# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        S.Brooker
_publ_contact_author_email       sbrooker@alkali.otago.ac.nz

_publ_section_title              
;
The tail that wags the dog: room-temperature
spin crossover and Langmuir-Blodgett film formation of an iron(II)
triazole complex featuring a long alkyl chain substituent
;
_publ_author_name                S.Brooker

# Attachment 'jakc16dpt.cif.txt'

data_jakc16dpt
_database_code_depnum_ccdc_archive 'CCDC 773454'
#TrackingRef 'jakc16dpt.cif.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H41 N5'
_chemical_formula_weight         447.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   65.021(8)
_cell_length_b                   4.6519(4)
_cell_length_c                   17.505(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.188(4)
_cell_angle_gamma                90.00
_cell_volume                     5109.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    3201
_cell_measurement_theta_min      2.327
_cell_measurement_theta_max      23.702

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8467
_exptl_absorpt_correction_T_max  0.9869
_exptl_absorpt_process_details   'SCALE(Bruker, 2004)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa Apex II area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            31132
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -80
_diffrn_reflns_limit_h_max       80
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         0.65
_diffrn_reflns_theta_max         26.40
_reflns_number_total             5212
_reflns_number_gt                3566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Entire C16-dpt molecule in asym unit. No solvent, no disorder. All non-H
ANIS. All H calc and ride. EXTI card used to correct for extinction.
The residual e density is +0.54/-0.45 which is fine.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0890P)^2^+1.9809P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0061(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5212
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2012
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.20429(3) 0.5341(4) 0.30819(12) 0.0263(5) Uani 1 1 d . . .
N2 N 0.21580(3) 0.6435(4) 0.51965(12) 0.0295(5) Uani 1 1 d . . .
N3 N 0.20437(3) 0.8040(4) 0.56009(12) 0.0299(5) Uani 1 1 d . . .
N4 N 0.15803(3) 1.2449(4) 0.47445(12) 0.0316(5) Uani 1 1 d . . .
N5 N 0.19090(3) 0.8788(4) 0.43207(11) 0.0219(5) Uani 1 1 d . . .
C1 C 0.21264(4) 0.3878(5) 0.25729(15) 0.0279(6) Uani 1 1 d . . .
H1 H 0.2046 0.3785 0.2036 0.033 Uiso 1 1 calc R . .
C2 C 0.23209(4) 0.2501(5) 0.27761(16) 0.0322(6) Uani 1 1 d . . .
H2 H 0.2369 0.1421 0.2395 0.039 Uiso 1 1 calc R . .
C3 C 0.24447(4) 0.2729(6) 0.35470(17) 0.0375(7) Uani 1 1 d . . .
H3 H 0.2581 0.1838 0.3706 0.045 Uiso 1 1 calc R . .
C4 C 0.23663(4) 0.4275(5) 0.40775(16) 0.0315(6) Uani 1 1 d . . .
H4 H 0.2449 0.4509 0.4608 0.038 Uiso 1 1 calc R . .
C5 C 0.21639(4) 0.5498(5) 0.38329(14) 0.0236(6) Uani 1 1 d . . .
C6 C 0.20763(4) 0.6909(5) 0.44324(14) 0.0226(5) Uani 1 1 d . . .
C7 C 0.18956(4) 0.9435(5) 0.50717(14) 0.0245(6) Uani 1 1 d . . .
C8 C 0.17446(4) 1.1416(5) 0.53035(14) 0.0247(6) Uani 1 1 d . . .
C9 C 0.17812(4) 1.2139(5) 0.61003(15) 0.0315(6) Uani 1 1 d . . .
H9 H 0.1900 1.1361 0.6484 0.038 Uiso 1 1 calc R . .
C10 C 0.16428(4) 1.4001(6) 0.63216(16) 0.0342(7) Uani 1 1 d . . .
H10 H 0.1664 1.4523 0.6861 0.041 Uiso 1 1 calc R . .
C11 C 0.14733(4) 1.5098(5) 0.57504(16) 0.0322(6) Uani 1 1 d . . .
H11 H 0.1376 1.6399 0.5886 0.039 Uiso 1 1 calc R . .
C12 C 0.14490(4) 1.4262(5) 0.49807(16) 0.0336(6) Uani 1 1 d . . .
H12 H 0.1331 1.5016 0.4589 0.040 Uiso 1 1 calc R . .
C13 C 0.17748(4) 0.9918(5) 0.35701(14) 0.0235(6) Uani 1 1 d . . .
H13A H 0.1854 0.9800 0.3160 0.028 Uiso 1 1 calc R . .
H13B H 0.1743 1.1968 0.3640 0.028 Uiso 1 1 calc R . .
C14 C 0.15665(4) 0.8275(5) 0.32894(14) 0.0251(6) Uani 1 1 d . . .
H14A H 0.1503 0.8002 0.3740 0.030 Uiso 1 1 calc R . .
H14B H 0.1596 0.6351 0.3099 0.030 Uiso 1 1 calc R . .
C15 C 0.14083(4) 0.9862(5) 0.26242(15) 0.0275(6) Uani 1 1 d . . .
H15A H 0.1365 1.1672 0.2837 0.033 Uiso 1 1 calc R . .
H15B H 0.1480 1.0374 0.2208 0.033 Uiso 1 1 calc R . .
C16 C 0.12099(4) 0.8108(6) 0.22538(14) 0.0285(6) Uani 1 1 d . . .
H16A H 0.1147 0.7424 0.2678 0.034 Uiso 1 1 calc R . .
H16B H 0.1252 0.6398 0.1993 0.034 Uiso 1 1 calc R . .
C17 C 0.10414(4) 0.9781(6) 0.16483(15) 0.0344(7) Uani 1 1 d . . .
H17A H 0.0988 1.1363 0.1924 0.041 Uiso 1 1 calc R . .
H17B H 0.1109 1.0659 0.1261 0.041 Uiso 1 1 calc R . .
C18 C 0.08524(4) 0.7998(6) 0.12021(15) 0.0368(7) Uani 1 1 d . . .
H18A H 0.0791 0.6994 0.1589 0.044 Uiso 1 1 calc R . .
H18B H 0.0903 0.6516 0.0889 0.044 Uiso 1 1 calc R . .
C19 C 0.06781(4) 0.9764(7) 0.06484(15) 0.0411(7) Uani 1 1 d . . .
H19A H 0.0623 1.1175 0.0969 0.049 Uiso 1 1 calc R . .
H19B H 0.0743 1.0859 0.0284 0.049 Uiso 1 1 calc R . .
C20 C 0.04929(4) 0.8045(7) 0.01603(16) 0.0447(8) Uani 1 1 d . . .
H20A H 0.0432 0.6883 0.0522 0.054 Uiso 1 1 calc R . .
H20B H 0.0547 0.6698 -0.0180 0.054 Uiso 1 1 calc R . .
C21 C 0.03163(4) 0.9847(8) -0.03605(16) 0.0478(8) Uani 1 1 d . . .
H21A H 0.0261 1.1167 -0.0018 0.057 Uiso 1 1 calc R . .
H21B H 0.0378 1.1041 -0.0713 0.057 Uiso 1 1 calc R . .
C22 C 0.01319(4) 0.8157(8) -0.08647(16) 0.0531(9) Uani 1 1 d . . .
H22A H 0.0070 0.6953 -0.0513 0.064 Uiso 1 1 calc R . .
H22B H 0.0187 0.6849 -0.1211 0.064 Uiso 1 1 calc R . .
C23 C -0.00444(4) 0.9983(8) -0.13781(16) 0.0549(10) Uani 1 1 d . . .
H23A H -0.0098 1.1300 -0.1031 0.066 Uiso 1 1 calc R . .
H23B H 0.0017 1.1180 -0.1730 0.066 Uiso 1 1 calc R . .
C24 C -0.02303(4) 0.8320(9) -0.18826(16) 0.0570(10) Uani 1 1 d . . .
H24A H -0.0294 0.7144 -0.1531 0.068 Uiso 1 1 calc R . .
H24B H -0.0176 0.6986 -0.2226 0.068 Uiso 1 1 calc R . .
C25 C -0.04046(4) 1.0170(9) -0.24024(16) 0.0567(10) Uani 1 1 d . . .
H25A H -0.0456 1.1528 -0.2059 0.068 Uiso 1 1 calc R . .
H25B H -0.0341 1.1323 -0.2759 0.068 Uiso 1 1 calc R . .
C26 C -0.05936(4) 0.8536(8) -0.29009(17) 0.0568(10) Uani 1 1 d . . .
H26A H -0.0658 0.7402 -0.2545 0.068 Uiso 1 1 calc R . .
H26B H -0.0542 0.7164 -0.3241 0.068 Uiso 1 1 calc R . .
C27 C -0.07646(4) 1.0410(8) -0.34222(17) 0.0549(9) Uani 1 1 d . . .
H27A H -0.0813 1.1827 -0.3084 0.066 Uiso 1 1 calc R . .
H27B H -0.0701 1.1493 -0.3792 0.066 Uiso 1 1 calc R . .
C28 C -0.09564(5) 0.8761(8) -0.38982(18) 0.0597(10) Uani 1 1 d . . .
H28A H -0.0910 0.7338 -0.4232 0.072 Uiso 1 1 calc R . .
H28B H -0.1057 1.0098 -0.4234 0.072 Uiso 1 1 calc R . .
H28C H -0.1026 0.7778 -0.3537 0.072 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0212(11) 0.0252(11) 0.0295(12) 0.0018(9) 0.0010(9) 0.0002(9)
N2 0.0237(11) 0.0297(11) 0.0311(13) 0.0051(9) 0.0003(9) 0.0008(9)
N3 0.0257(12) 0.0314(11) 0.0282(12) 0.0030(9) -0.0010(10) -0.0007(10)
N4 0.0347(13) 0.0278(11) 0.0314(12) 0.0065(9) 0.0067(10) 0.0067(10)
N5 0.0188(10) 0.0177(10) 0.0255(12) 0.0026(8) -0.0007(8) -0.0006(8)
C1 0.0222(13) 0.0283(13) 0.0310(15) -0.0009(11) 0.0033(11) 0.0003(11)
C2 0.0272(14) 0.0273(13) 0.0422(17) 0.0034(11) 0.0094(12) -0.0001(11)
C3 0.0230(14) 0.0350(15) 0.0517(18) 0.0089(13) 0.0049(13) 0.0087(12)
C4 0.0218(13) 0.0313(13) 0.0358(15) 0.0060(11) -0.0024(11) 0.0024(11)
C5 0.0197(13) 0.0152(11) 0.0323(14) 0.0057(10) 0.0003(10) -0.0027(9)
C6 0.0169(12) 0.0186(11) 0.0267(13) 0.0053(10) -0.0043(10) -0.0020(10)
C7 0.0225(13) 0.0214(12) 0.0250(14) 0.0036(10) -0.0020(10) -0.0070(10)
C8 0.0248(13) 0.0194(12) 0.0280(14) 0.0017(10) 0.0034(11) -0.0059(10)
C9 0.0272(14) 0.0346(14) 0.0304(15) 0.0005(11) 0.0033(11) -0.0075(12)
C10 0.0323(15) 0.0409(15) 0.0299(15) -0.0049(12) 0.0092(12) -0.0122(13)
C11 0.0347(16) 0.0272(13) 0.0392(16) -0.0030(11) 0.0179(13) -0.0058(12)
C12 0.0355(16) 0.0287(14) 0.0363(16) 0.0051(11) 0.0091(12) 0.0042(12)
C13 0.0234(13) 0.0205(11) 0.0235(13) 0.0067(10) 0.0009(10) 0.0037(10)
C14 0.0214(13) 0.0273(13) 0.0244(13) 0.0060(10) 0.0021(10) 0.0027(10)
C15 0.0226(13) 0.0307(13) 0.0270(14) 0.0068(11) 0.0025(11) 0.0085(11)
C16 0.0226(13) 0.0398(14) 0.0211(13) 0.0048(11) 0.0021(10) 0.0074(11)
C17 0.0244(14) 0.0485(16) 0.0268(14) 0.0085(12) 0.0004(11) 0.0084(12)
C18 0.0220(14) 0.0622(18) 0.0230(14) 0.0068(13) 0.0002(11) 0.0126(13)
C19 0.0279(15) 0.069(2) 0.0225(14) 0.0041(13) 0.0004(12) 0.0196(14)
C20 0.0229(14) 0.086(2) 0.0221(14) 0.0036(14) 0.0004(11) 0.0144(15)
C21 0.0224(15) 0.097(2) 0.0213(15) 0.0055(15) 0.0003(12) 0.0204(15)
C22 0.0236(15) 0.110(3) 0.0228(15) 0.0024(16) 0.0011(12) 0.0188(17)
C23 0.0250(16) 0.115(3) 0.0227(15) 0.0039(17) 0.0032(12) 0.0225(17)
C24 0.0265(16) 0.123(3) 0.0192(15) 0.0049(16) 0.0015(12) 0.0239(18)
C25 0.0242(16) 0.121(3) 0.0213(15) 0.0037(16) 0.0000(12) 0.0260(17)
C26 0.0259(16) 0.115(3) 0.0263(16) 0.0052(17) 0.0013(13) 0.0196(18)
C27 0.0231(15) 0.111(3) 0.0254(16) 0.0016(16) -0.0034(12) 0.0226(17)
C28 0.0290(16) 0.111(3) 0.0330(17) 0.0049(18) -0.0023(13) 0.0184(18)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.344(3) . ?
N1 C5 1.346(3) . ?
N2 C6 1.322(3) . ?
N2 N3 1.374(3) . ?
N3 C7 1.319(3) . ?
N4 C8 1.335(3) . ?
N4 C12 1.340(3) . ?
N5 C6 1.369(3) . ?
N5 C7 1.373(3) . ?
N5 C13 1.471(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.473(3) . ?
C7 C8 1.479(3) . ?
C8 C9 1.393(4) . ?
C9 C10 1.376(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.521(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.527(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.521(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.518(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.524(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.510(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.518(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.510(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.518(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.510(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.521(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.512(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.516(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.515(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.2(2) . . ?
C6 N2 N3 107.60(19) . . ?
C7 N3 N2 107.4(2) . . ?
C8 N4 C12 116.9(2) . . ?
C6 N5 C7 104.51(19) . . ?
C6 N5 C13 128.2(2) . . ?
C7 N5 C13 127.3(2) . . ?
N1 C1 C2 124.5(2) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 118.5(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 118.4(2) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 C6 118.9(2) . . ?
C4 C5 C6 118.3(2) . . ?
N2 C6 N5 110.2(2) . . ?
N2 C6 C5 121.2(2) . . ?
N5 C6 C5 128.6(2) . . ?
N3 C7 N5 110.3(2) . . ?
N3 C7 C8 122.0(2) . . ?
N5 C7 C8 127.8(2) . . ?
N4 C8 C9 122.8(2) . . ?
N4 C8 C7 119.0(2) . . ?
C9 C8 C7 118.3(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 119.1(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
N4 C12 C11 124.3(2) . . ?
N4 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
N5 C13 C14 112.26(18) . . ?
N5 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N5 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.61(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 113.1(2) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 C17 113.4(2) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 114.6(2) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 113.5(2) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 115.1(3) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 C21 114.4(3) . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C21 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C20 115.1(3) . . ?
C22 C21 H21A 108.5 . . ?
C20 C21 H21A 108.5 . . ?
C22 C21 H21B 108.5 . . ?
C20 C21 H21B 108.5 . . ?
H21A C21 H21B 107.5 . . ?
C21 C22 C23 114.6(3) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 115.1(3) . . ?
C24 C23 H23A 108.5 . . ?
C22 C23 H23A 108.5 . . ?
C24 C23 H23B 108.5 . . ?
C22 C23 H23B 108.5 . . ?
H23A C23 H23B 107.5 . . ?
C23 C24 C25 114.6(3) . . ?
C23 C24 H24A 108.6 . . ?
C25 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C25 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 115.2(3) . . ?
C26 C25 H25A 108.5 . . ?
C24 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C24 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C25 C26 C27 114.5(3) . . ?
C25 C26 H26A 108.6 . . ?
C27 C26 H26A 108.6 . . ?
C25 C26 H26B 108.6 . . ?
C27 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C28 C27 C26 114.1(3) . . ?
C28 C27 H27A 108.7 . . ?
C26 C27 H27A 108.7 . . ?
C28 C27 H27B 108.7 . . ?
C26 C27 H27B 108.7 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 C7 0.2(2) . . . . ?
C5 N1 C1 C2 1.8(3) . . . . ?
N1 C1 C2 C3 -3.0(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
C1 N1 C5 C4 1.2(3) . . . . ?
C1 N1 C5 C6 -176.1(2) . . . . ?
C3 C4 C5 N1 -2.9(4) . . . . ?
C3 C4 C5 C6 174.4(2) . . . . ?
N3 N2 C6 N5 -0.3(2) . . . . ?
N3 N2 C6 C5 179.9(2) . . . . ?
C7 N5 C6 N2 0.3(2) . . . . ?
C13 N5 C6 N2 179.4(2) . . . . ?
C7 N5 C6 C5 -179.9(2) . . . . ?
C13 N5 C6 C5 -0.9(4) . . . . ?
N1 C5 C6 N2 160.6(2) . . . . ?
C4 C5 C6 N2 -16.8(3) . . . . ?
N1 C5 C6 N5 -19.2(3) . . . . ?
C4 C5 C6 N5 163.5(2) . . . . ?
N2 N3 C7 N5 0.0(3) . . . . ?
N2 N3 C7 C8 -179.08(19) . . . . ?
C6 N5 C7 N3 -0.2(2) . . . . ?
C13 N5 C7 N3 -179.2(2) . . . . ?
C6 N5 C7 C8 178.8(2) . . . . ?
C13 N5 C7 C8 -0.2(4) . . . . ?
C12 N4 C8 C9 0.3(3) . . . . ?
C12 N4 C8 C7 -179.3(2) . . . . ?
N3 C7 C8 N4 -170.7(2) . . . . ?
N5 C7 C8 N4 10.4(4) . . . . ?
N3 C7 C8 C9 9.7(3) . . . . ?
N5 C7 C8 C9 -169.2(2) . . . . ?
N4 C8 C9 C10 -0.2(4) . . . . ?
C7 C8 C9 C10 179.4(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C8 N4 C12 C11 -0.1(4) . . . . ?
C10 C11 C12 N4 -0.3(4) . . . . ?
C6 N5 C13 C14 97.7(3) . . . . ?
C7 N5 C13 C14 -83.4(3) . . . . ?
N5 C13 C14 C15 166.9(2) . . . . ?
C13 C14 C15 C16 172.3(2) . . . . ?
C14 C15 C16 C17 174.1(2) . . . . ?
C15 C16 C17 C18 173.5(2) . . . . ?
C16 C17 C18 C19 175.4(2) . . . . ?
C17 C18 C19 C20 176.8(2) . . . . ?
C18 C19 C20 C21 177.4(2) . . . . ?
C19 C20 C21 C22 178.8(2) . . . . ?
C20 C21 C22 C23 179.6(2) . . . . ?
C21 C22 C23 C24 -179.7(2) . . . . ?
C22 C23 C24 C25 -179.2(2) . . . . ?
C23 C24 C25 C26 -179.0(2) . . . . ?
C24 C25 C26 C27 -179.4(3) . . . . ?
C25 C26 C27 C28 -178.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.156