#------------------------------------------------------------------------------
#$Date: 2025-11-25 12:44:40 +0100 (Tue 25 de Nov de 2025) $
#$Revision: 303376 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/12/7251282.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251282
loop_
_publ_author_name
'Thakur, Jyoti Swarup'
'Dash, Omkar'
'Bhale, Nagesh A.'
'Mondal, Pradip Kumar'
'Dikundwar, Amol Gopalrao'
'Polentarutti, Maurizio'
'Nayak, Susanta K.'
_publ_section_title
;
 Structural and computational study of reversibly photo switchable
 (E)-4-((4-alkoxyphenyl)diazenyl)benzonitrile based liquid crystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00980D
_journal_year                    2025
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_chemical_name_common            Azonitrile
_chemical_name_systematic        (E)-4-((4-propoxyphenyl)diazenyl)benzonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                73.39(3)
_cell_angle_beta                 87.85(3)
_cell_angle_gamma                88.91(3)
_cell_formula_units_Z            6
_cell_length_a                   5.9500(12)
_cell_length_b                   18.537(4)
_cell_length_c                   19.114(4)
_cell_measurement_reflns_used    11765
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      1.1
_cell_volume                     2018.7(8)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35341
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.749
_diffrn_reflns_theta_min         1.096
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      1.31
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         11765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0632
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1331P)²+0.2051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10388
_reflns_number_total             11765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00980d3.cif
_cod_data_source_block           AZN-3
_cod_database_code               7251282
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(O4)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=1-FVAR(1)
 Sof(O3)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C14(H14A,
 H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B)
3.b Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C49(H49A,H49B,H49C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C34(H34),
  C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.10012(10) 0.15957(3) 0.01778(3) 0.02508(14) Uani 1 1 d . . . . .
O2 O -0.13024(10) 0.47364(4) 0.29982(3) 0.02564(14) Uani 1 1 d . . . . .
O3 O -0.0472(3) 0.17000(11) 0.64092(10) 0.0297(4) Uani 0.531(3) 1 d . . P A 1
C46 C 0.0285(4) 0.21809(12) 0.68178(12) 0.0364(5) Uani 0.531(3) 1 d . . P A 1
H46A H 0.066224 0.268288 0.648469 0.044 Uiso 0.531(3) 1 calc R U P A 1
H46B H 0.164842 0.196397 0.708381 0.044 Uiso 0.531(3) 1 calc R U P A 1
C47 C -0.1583(4) 0.22520(12) 0.73520(11) 0.0409(6) Uani 0.531(3) 1 d . . P A 1
H47A H -0.207261 0.174159 0.763668 0.049 Uiso 0.531(3) 1 calc R U P A 1
H47B H -0.099149 0.250320 0.769868 0.049 Uiso 0.531(3) 1 calc R U P A 1
C51 C -0.3543(6) 0.2679(2) 0.69992(15) 0.0814(13) Uani 0.531(3) 1 d . . P A 1
H51A H -0.469105 0.270548 0.737284 0.122 Uiso 0.531(3) 1 calc R U P A 1
H51B H -0.308207 0.318993 0.672587 0.122 Uiso 0.531(3) 1 calc R U P A 1
H51C H -0.416405 0.242771 0.666382 0.122 Uiso 0.531(3) 1 calc R U P A 1
C48 C -0.2693(3) 0.21684(12) 0.70238(12) 0.0333(5) Uani 0.469(3) 1 d . . P A 2
H48A H -0.395324 0.228972 0.668439 0.040 Uiso 0.469(3) 1 calc R U P A 2
H48B H -0.304416 0.168984 0.740085 0.040 Uiso 0.469(3) 1 calc R U P A 2
C49 C -0.2470(5) 0.27852(17) 0.73831(18) 0.0533(8) Uani 0.469(3) 1 d . . P A 2
H49A H -0.387789 0.283526 0.764880 0.080 Uiso 0.469(3) 1 calc R U P A 2
H49B H -0.123916 0.266162 0.772527 0.080 Uiso 0.469(3) 1 calc R U P A 2
H49C H -0.214730 0.326089 0.700954 0.080 Uiso 0.469(3) 1 calc R U P A 2
O4 O -0.0960(3) 0.15126(12) 0.62452(10) 0.0268(4) Uani 0.469(3) 1 d . . P A 2
C50 C -0.0556(4) 0.20725(12) 0.66077(13) 0.0272(4) Uani 0.469(3) 1 d . . P A 2
H50A H -0.014286 0.255494 0.624609 0.033 Uiso 0.469(3) 1 calc R U P A 2
H50B H 0.069270 0.191091 0.694748 0.033 Uiso 0.469(3) 1 calc R U P A 2
N1 N 0.53556(12) 0.26193(4) 0.25255(4) 0.02114(14) Uani 1 1 d . . . . .
N2 N 0.47525(12) 0.21598(4) 0.21947(4) 0.02119(14) Uani 1 1 d . . . . .
N3 N -0.20970(14) 0.33428(5) 0.50147(5) 0.03692(19) Uani 1 1 d . . . . .
N4 N 0.47342(12) 0.38718(4) 0.06444(4) 0.02255(15) Uani 1 1 d . . . . .
N5 N 0.51994(12) 0.43472(4) 0.09759(4) 0.02232(15) Uani 1 1 d . . . . .
N6 N 1.24470(14) 0.34510(5) -0.19108(5) 0.03672(19) Uani 1 1 d . . . . .
N7 N 0.46016(13) 0.05327(4) 0.39508(4) 0.02975(17) Uani 1 1 d . . . . .
N8 N 0.52338(13) 0.10076(5) 0.42566(4) 0.02744(16) Uani 1 1 d . . . . .
N9 N 1.19195(17) -0.02233(6) 0.14412(5) 0.0435(2) Uani 1 1 d . . . . .
C1 C 0.37080(13) 0.27388(4) 0.30436(4) 0.02006(15) Uani 1 1 d . . . . .
C2 C 0.16211(13) 0.23860(4) 0.31809(4) 0.02201(16) Uani 1 1 d . . . . .
H2 H 0.122963 0.204004 0.292345 0.026 Uiso 1 1 calc R U . . .
C3 C 0.01209(13) 0.25397(5) 0.36916(4) 0.02313(16) Uani 1 1 d . . . . .
H3 H -0.130433 0.230239 0.378552 0.028 Uiso 1 1 calc R U . . .
C4 C 0.07270(14) 0.30489(5) 0.40685(4) 0.02313(16) Uani 1 1 d . . . . .
C5 C 0.28148(14) 0.34005(5) 0.39353(4) 0.02412(16) Uani 1 1 d . . . . .
H5 H 0.321436 0.374282 0.419586 0.029 Uiso 1 1 calc R U . . .
C6 C 0.43070(13) 0.32462(4) 0.34182(4) 0.02230(16) Uani 1 1 d . . . . .
H6 H 0.572873 0.348562 0.332078 0.027 Uiso 1 1 calc R U . . .
C7 C 0.63779(13) 0.20379(4) 0.16792(4) 0.01984(15) Uani 1 1 d . . . . .
C8 C 0.57762(13) 0.15481(4) 0.12861(4) 0.02247(16) Uani 1 1 d . . . . .
H8 H 0.433725 0.131985 0.137121 0.027 Uiso 1 1 calc R U . . .
C9 C 0.72681(14) 0.13905(5) 0.07695(4) 0.02375(16) Uani 1 1 d . . . . .
H9 H 0.684488 0.106017 0.049894 0.029 Uiso 1 1 calc R U . . .
C10 C 0.93856(13) 0.17202(4) 0.06515(4) 0.02110(15) Uani 1 1 d . . . . .
C11 C 0.99904(13) 0.22202(4) 0.10427(4) 0.02088(15) Uani 1 1 d . . . . .
H11 H 1.142543 0.245114 0.095657 0.025 Uiso 1 1 calc R U . . .
C12 C 0.84994(13) 0.23747(4) 0.15509(4) 0.02067(15) Uani 1 1 d . . . . .
H12 H 0.891207 0.271150 0.181586 0.025 Uiso 1 1 calc R U . . .
C13 C -0.08356(15) 0.32119(5) 0.45963(5) 0.02782(18) Uani 1 1 d . . . . .
C14 C 1.05475(14) 0.10573(5) -0.02095(5) 0.02779(17) Uani 1 1 d . . . . .
H14A H 0.945552 0.126993 -0.059481 0.033 Uiso 1 1 calc R U . . .
H14B H 0.990106 0.059500 0.013053 0.033 Uiso 1 1 calc R U . . .
C15 C 1.27409(14) 0.08757(5) -0.05464(5) 0.02707(17) Uani 1 1 d . . . . .
H15A H 1.247014 0.048618 -0.079525 0.032 Uiso 1 1 calc R U . . .
H15B H 1.380280 0.066103 -0.015212 0.032 Uiso 1 1 calc R U . . .
C16 C 1.38216(18) 0.15495(5) -0.10907(6) 0.0389(2) Uani 1 1 d . . . . .
H16A H 1.280475 0.175558 -0.149260 0.058 Uiso 1 1 calc R U . . .
H16B H 1.523948 0.139360 -0.128409 0.058 Uiso 1 1 calc R U . . .
H16C H 1.411987 0.193546 -0.084754 0.058 Uiso 1 1 calc R U . . .
C17 C 0.64472(13) 0.37943(4) 0.01283(4) 0.02165(16) Uani 1 1 d . . . . .
C18 C 0.84893(14) 0.41745(5) 0.00198(4) 0.02360(16) Uani 1 1 d . . . . .
H18 H 0.880755 0.450539 0.030132 0.028 Uiso 1 1 calc R U . . .
C19 C 1.00515(14) 0.40694(5) -0.04978(4) 0.02436(17) Uani 1 1 d . . . . .
H19 H 1.144772 0.432504 -0.057212 0.029 Uiso 1 1 calc R U . . .
C20 C 0.95547(14) 0.35833(5) -0.09105(4) 0.02436(17) Uani 1 1 d . . . . .
C21 C 0.75216(15) 0.31974(5) -0.08002(5) 0.02658(17) Uani 1 1 d . . . . .
H21 H 0.720217 0.286608 -0.108116 0.032 Uiso 1 1 calc R U . . .
C22 C 0.59702(14) 0.33018(5) -0.02765(5) 0.02488(17) Uani 1 1 d . . . . .
H22 H 0.458688 0.303822 -0.019410 0.030 Uiso 1 1 calc R U . . .
C23 C 0.35081(13) 0.44328(4) 0.14879(4) 0.02048(15) Uani 1 1 d . . . . .
C24 C 0.14483(13) 0.40544(4) 0.15994(4) 0.02211(16) Uani 1 1 d . . . . .
H24 H 0.113354 0.371502 0.132645 0.027 Uiso 1 1 calc R U . . .
C25 C -0.01182(13) 0.41743(4) 0.21042(4) 0.02226(16) Uani 1 1 d . . . . .
H25 H -0.152004 0.392227 0.217530 0.027 Uiso 1 1 calc R U . . .
C26 C 0.03566(14) 0.46689(5) 0.25135(4) 0.02205(16) Uani 1 1 d . . . . .
C27 C 0.24050(14) 0.50473(5) 0.24048(4) 0.02361(16) Uani 1 1 d . . . . .
H27 H 0.272654 0.538393 0.268000 0.028 Uiso 1 1 calc R U . . .
C28 C 0.39713(14) 0.49264(5) 0.18894(4) 0.02329(16) Uani 1 1 d . . . . .
H28 H 0.536578 0.518316 0.181191 0.028 Uiso 1 1 calc R U . . .
C29 C 1.11572(15) 0.35019(5) -0.14645(5) 0.02788(18) Uani 1 1 d . . . . .
C30 C -0.09347(15) 0.52170(5) 0.34506(5) 0.02683(17) Uani 1 1 d . . . . .
H30A H -0.046335 0.572224 0.314646 0.032 Uiso 1 1 calc R U . . .
H30B H 0.026237 0.500398 0.379847 0.032 Uiso 1 1 calc R U . . .
C31 C -0.31150(15) 0.52728(5) 0.38587(5) 0.03169(19) Uani 1 1 d . . . . .
H31A H -0.364113 0.476024 0.412197 0.038 Uiso 1 1 calc R U . . .
H31B H -0.426892 0.551736 0.350573 0.038 Uiso 1 1 calc R U . . .
C32 C -0.2853(2) 0.57205(7) 0.44003(7) 0.0458(3) Uani 1 1 d . . . . .
H32A H -0.223822 0.621688 0.414609 0.069 Uiso 1 1 calc R U . . .
H32B H -0.182741 0.545261 0.477958 0.069 Uiso 1 1 calc R U . . .
H32C H -0.432402 0.578175 0.462567 0.069 Uiso 1 1 calc R U . . .
C33 C 0.62155(15) 0.03957(5) 0.34321(5) 0.02688(18) Uani 1 1 d . . . . .
C34 C 0.83217(15) 0.07358(5) 0.32866(5) 0.02667(17) Uani 1 1 d . . . . .
H34 H 0.875061 0.107889 0.354259 0.032 Uiso 1 1 calc R U . . .
C35 C 0.97847(15) 0.05751(5) 0.27715(5) 0.02669(17) Uani 1 1 d . . . . .
H35 H 1.121821 0.080625 0.267135 0.032 Uiso 1 1 calc R U . . .
C36 C 0.91317(16) 0.00678(5) 0.23986(5) 0.02882(18) Uani 1 1 d . . . . .
C37 C 0.70319(17) -0.02741(5) 0.25427(6) 0.0342(2) Uani 1 1 d . . . . .
H37 H 0.659927 -0.061578 0.228563 0.041 Uiso 1 1 calc R U . . .
C38 C 0.55767(16) -0.01128(5) 0.30635(6) 0.0324(2) Uani 1 1 d . . . . .
H38 H 0.414998 -0.034819 0.316851 0.039 Uiso 1 1 calc R U . . .
C39 C 0.36613(14) 0.11519(5) 0.47748(5) 0.0303(2) Uani 1 1 d . . . . .
C40 C 0.15339(16) 0.08198(7) 0.49343(6) 0.0415(3) Uani 1 1 d . . . . .
H40 H 0.106559 0.047833 0.468186 0.050 Uiso 1 1 calc R U . . .
C41 C 0.01237(17) 0.09861(8) 0.54543(7) 0.0519(4) Uani 1 1 d . . . . .
H41 H -0.131240 0.075778 0.556285 0.062 Uiso 1 1 calc R U . . .
C42 C 0.08106(19) 0.14946(8) 0.58251(6) 0.0506(4) Uani 1 1 d . . . . .
C43 C 0.28892(19) 0.18360(7) 0.56598(6) 0.0430(3) Uani 1 1 d . . . . .
H43 H 0.334199 0.218843 0.590201 0.052 Uiso 1 1 calc R U . . .
C44 C 0.43135(16) 0.16591(6) 0.51356(5) 0.0328(2) Uani 1 1 d . . . . .
H44 H 0.574663 0.188923 0.502479 0.039 Uiso 1 1 calc R U . . .
C45 C 1.06728(18) -0.00951(6) 0.18634(6) 0.0339(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C10 O1 C14 117.93(7) . . ?
C26 O2 C30 118.35(7) . . ?
C46 O3 C42 125.77(17) . . ?
O3 C46 H46A 110.1 . . ?
O3 C46 H46B 110.1 . . ?
O3 C46 C47 108.08(19) . . ?
H46A C46 H46B 108.4 . . ?
C47 C46 H46A 110.1 . . ?
C47 C46 H46B 110.1 . . ?
C46 C47 H47A 108.9 . . ?
C46 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
C51 C47 C46 113.40(18) . . ?
C51 C47 H47A 108.9 . . ?
C51 C47 H47B 108.9 . . ?
C47 C51 H51A 109.5 . . ?
C47 C51 H51B 109.5 . . ?
C47 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
H48A C48 H48B 108.0 . . ?
C49 C48 H48A 109.4 . . ?
C49 C48 H48B 109.4 . . ?
C49 C48 C50 111.18(19) . . ?
C50 C48 H48A 109.4 . . ?
C50 C48 H48B 109.4 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C42 O4 C50 106.87(18) . . ?
C48 C50 H50A 110.2 . . ?
C48 C50 H50B 110.2 . . ?
O4 C50 C48 107.6(2) . . ?
O4 C50 H50A 110.2 . . ?
O4 C50 H50B 110.2 . . ?
H50A C50 H50B 108.5 . . ?
N2 N1 C1 113.58(7) . . ?
N1 N2 C7 113.97(7) . . ?
N5 N4 C17 113.34(8) . . ?
N4 N5 C23 113.98(7) . . ?
N8 N7 C33 113.41(8) . . ?
N7 N8 C39 114.45(8) . . ?
C2 C1 N1 124.07(7) . . ?
C6 C1 N1 115.33(7) . . ?
C6 C1 C2 120.60(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(8) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(8) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C13 119.29(8) . . ?
C5 C4 C3 120.87(8) . . ?
C5 C4 C13 119.83(8) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.49(8) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.71(8) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 N2 116.33(7) . . ?
C8 C7 C12 119.58(7) . . ?
C12 C7 N2 124.09(7) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.48(7) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.60(7) . . ?
C10 C9 H9 120.2 . . ?
O1 C10 C9 125.03(7) . . ?
O1 C10 C11 114.91(7) . . ?
C9 C10 C11 120.05(7) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.91(7) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.36(7) . . ?
C11 C12 H12 119.8 . . ?
N3 C13 C4 179.51(10) . . ?
O1 C14 H14A 110.1 . . ?
O1 C14 H14B 110.1 . . ?
O1 C14 C15 107.80(7) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.73(8) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N4 123.89(8) . . ?
C22 C17 N4 115.59(7) . . ?
C22 C17 C18 120.52(8) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.99(8) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.35(8) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 C29 118.69(8) . . ?
C21 C20 C19 120.87(8) . . ?
C21 C20 C29 120.43(8) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.43(8) . . ?
C22 C21 H21 120.3 . . ?
C17 C22 H22 120.1 . . ?
C21 C22 C17 119.82(8) . . ?
C21 C22 H22 120.1 . . ?
C24 C23 N5 123.66(7) . . ?
C28 C23 N5 116.40(7) . . ?
C28 C23 C24 119.94(8) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.06(8) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 119.99(7) . . ?
C26 C25 H25 120.0 . . ?
O2 C26 C25 114.70(7) . . ?
O2 C26 C27 125.10(8) . . ?
C27 C26 C25 120.20(8) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.38(8) . . ?
C28 C27 H27 120.3 . . ?
C23 C28 C27 120.43(8) . . ?
C23 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
N6 C29 C20 178.72(9) . . ?
O2 C30 H30A 110.2 . . ?
O2 C30 H30B 110.2 . . ?
O2 C30 C31 107.54(7) . . ?
H30A C30 H30B 108.5 . . ?
C31 C30 H30A 110.2 . . ?
C31 C30 H30B 110.2 . . ?
C30 C31 H31A 109.3 . . ?
C30 C31 H31B 109.3 . . ?
C30 C31 C32 111.64(8) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 N7 123.87(9) . . ?
C38 C33 N7 115.79(8) . . ?
C38 C33 C34 120.34(9) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.23(9) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.4 . . ?
C34 C35 C36 119.29(8) . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C45 118.73(9) . . ?
C37 C36 C35 120.71(9) . . ?
C37 C36 C45 120.56(9) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.66(9) . . ?
C38 C37 H37 120.2 . . ?
C33 C38 H38 120.1 . . ?
C37 C38 C33 119.77(9) . . ?
C37 C38 H38 120.1 . . ?
C40 C39 N8 124.28(11) . . ?
C44 C39 N8 116.25(8) . . ?
C44 C39 C40 119.46(10) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.30(13) . . ?
C41 C40 H40 119.8 . . ?
C40 C41 H41 120.1 . . ?
C40 C41 C42 119.88(11) . . ?
C42 C41 H41 120.1 . . ?
O4 C42 C41 101.27(15) . . ?
O4 C42 C43 138.55(19) . . ?
C41 C42 O3 125.76(14) . . ?
C43 C42 O3 114.10(17) . . ?
C43 C42 C41 120.12(11) . . ?
C42 C43 H43 120.2 . . ?
C42 C43 C44 119.54(13) . . ?
C44 C43 H43 120.2 . . ?
C39 C44 C43 120.68(10) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
N9 C45 C36 179.25(11) . . ?
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
O1 C10 1.3576(10) . ?
O1 C14 1.4368(10) . ?
O2 C26 1.3569(10) . ?
O2 C30 1.4323(10) . ?
O3 C46 1.431(3) . ?
O3 C42 1.464(2) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.511(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C51 1.470(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.503(3) . ?
C48 C50 1.509(3) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
O4 C50 1.431(3) . ?
O4 C42 1.3060(19) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
N1 N2 1.2612(10) . ?
N1 C1 1.4266(10) . ?
N2 C7 1.4159(11) . ?
N3 C13 1.1493(12) . ?
N4 N5 1.2636(11) . ?
N4 C17 1.4257(11) . ?
N5 C23 1.4158(11) . ?
N6 C29 1.1488(12) . ?
N7 N8 1.2575(13) . ?
N7 C33 1.4257(13) . ?
N8 C39 1.4144(12) . ?
N9 C45 1.1472(15) . ?
C1 C2 1.3952(12) . ?
C1 C6 1.3934(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.3837(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.4005(12) . ?
C4 C5 1.3946(12) . ?
C4 C13 1.4375(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.3904(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.3927(11) . ?
C7 C12 1.4010(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.3921(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.3931(12) . ?
C10 C11 1.4059(11) . ?
C11 H11 0.9500 . ?
C11 C12 1.3776(11) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5085(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5144(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.3950(12) . ?
C17 C22 1.3939(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.3839(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.3984(12) . ?
C20 C21 1.3954(13) . ?
C20 C29 1.4364(12) . ?
C21 H21 0.9500 . ?
C21 C22 1.3879(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.4026(12) . ?
C23 C28 1.3889(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.3771(11) . ?
C25 H25 0.9500 . ?
C25 C26 1.4032(12) . ?
C26 C27 1.3967(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.3924(11) . ?
C28 H28 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.5058(12) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.5142(13) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.3961(13) . ?
C33 C38 1.3939(14) . ?
C34 H34 0.9500 . ?
C34 C35 1.3819(13) . ?
C35 H35 0.9500 . ?
C35 C36 1.4003(12) . ?
C36 C37 1.3939(14) . ?
C36 C45 1.4403(14) . ?
C37 H37 0.9500 . ?
C37 C38 1.3878(15) . ?
C38 H38 0.9500 . ?
C39 C40 1.4027(14) . ?
C39 C44 1.3839(16) . ?
C40 H40 0.9500 . ?
C40 C41 1.3747(17) . ?
C41 H41 0.9500 . ?
C41 C42 1.406(2) . ?
C42 C43 1.3842(19) . ?
C43 H43 0.9500 . ?
C43 C44 1.3941(14) . ?
C44 H44 0.9500 . ?
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
O1 C10 C11 C12 -178.53(6) . . . . ?
O1 C14 C15 C16 -61.28(10) . . . . ?
O2 C26 C27 C28 179.87(7) . . . . ?
O2 C30 C31 C32 175.41(8) . . . . ?
O3 C46 C47 C51 -69.0(3) . . . . ?
O3 C42 C43 C44 177.10(9) . . . . ?
C46 O3 C42 C41 175.84(14) . . . . ?
C46 O3 C42 C43 -2.6(2) . . . . ?
C49 C48 C50 O4 -176.3(2) . . . . ?
O4 C42 C43 C44 -177.98(15) . . . . ?
C50 O4 C42 C41 -174.61(13) . . . . ?
C50 O4 C42 C43 2.3(2) . . . . ?
N1 N2 C7 C8 -178.57(6) . . . . ?
N1 N2 C7 C12 1.58(11) . . . . ?
N1 C1 C2 C3 -179.64(6) . . . . ?
N1 C1 C6 C5 -179.97(6) . . . . ?
N2 N1 C1 C2 0.11(11) . . . . ?
N2 N1 C1 C6 -179.69(6) . . . . ?
N2 C7 C8 C9 -179.70(6) . . . . ?
N2 C7 C12 C11 179.46(6) . . . . ?
N4 N5 C23 C24 -2.82(12) . . . . ?
N4 N5 C23 C28 177.48(7) . . . . ?
N4 C17 C18 C19 -179.52(6) . . . . ?
N4 C17 C22 C21 179.07(6) . . . . ?
N5 N4 C17 C18 2.98(12) . . . . ?
N5 N4 C17 C22 -177.16(7) . . . . ?
N5 C23 C24 C25 -179.40(6) . . . . ?
N5 C23 C28 C27 179.89(6) . . . . ?
N7 N8 C39 C40 -1.69(13) . . . . ?
N7 N8 C39 C44 178.63(7) . . . . ?
N7 C33 C34 C35 -179.63(7) . . . . ?
N7 C33 C38 C37 179.28(7) . . . . ?
N8 N7 C33 C34 1.64(12) . . . . ?
N8 N7 C33 C38 -178.47(7) . . . . ?
N8 C39 C40 C41 179.15(8) . . . . ?
N8 C39 C44 C43 -179.61(7) . . . . ?
C1 N1 N2 C7 180.00(5) . . . . ?
C1 C2 C3 C4 -0.25(12) . . . . ?
C2 C1 C6 C5 0.22(12) . . . . ?
C2 C3 C4 C5 -0.02(12) . . . . ?
C2 C3 C4 C13 179.66(6) . . . . ?
C3 C4 C5 C6 0.38(12) . . . . ?
C4 C5 C6 C1 -0.48(12) . . . . ?
C6 C1 C2 C3 0.15(12) . . . . ?
C7 C8 C9 C10 0.66(12) . . . . ?
C8 C7 C12 C11 -0.39(12) . . . . ?
C8 C9 C10 O1 178.25(7) . . . . ?
C8 C9 C10 C11 -1.23(12) . . . . ?
C9 C10 C11 C12 1.00(12) . . . . ?
C10 O1 C14 C15 -166.11(7) . . . . ?
C10 C11 C12 C7 -0.19(12) . . . . ?
C12 C7 C8 C9 0.15(12) . . . . ?
C13 C4 C5 C6 -179.30(7) . . . . ?
C14 O1 C10 C9 -3.04(12) . . . . ?
C14 O1 C10 C11 176.46(7) . . . . ?
C17 N4 N5 C23 179.71(5) . . . . ?
C17 C18 C19 C20 0.31(12) . . . . ?
C18 C17 C22 C21 -1.07(13) . . . . ?
C18 C19 C20 C21 -0.81(12) . . . . ?
C18 C19 C20 C29 177.69(7) . . . . ?
C19 C20 C21 C22 0.37(13) . . . . ?
C20 C21 C22 C17 0.57(13) . . . . ?
C22 C17 C18 C19 0.62(12) . . . . ?
C23 C24 C25 C26 -0.74(12) . . . . ?
C24 C23 C28 C27 0.18(12) . . . . ?
C24 C25 C26 O2 -179.39(6) . . . . ?
C24 C25 C26 C27 0.74(12) . . . . ?
C25 C26 C27 C28 -0.27(12) . . . . ?
C26 O2 C30 C31 172.56(7) . . . . ?
C26 C27 C28 C23 -0.19(12) . . . . ?
C28 C23 C24 C25 0.28(12) . . . . ?
C29 C20 C21 C22 -178.11(7) . . . . ?
C30 O2 C26 C25 178.59(6) . . . . ?
C30 O2 C26 C27 -1.54(12) . . . . ?
C33 N7 N8 C39 -179.88(6) . . . . ?
C33 C34 C35 C36 -0.05(13) . . . . ?
C34 C33 C38 C37 -0.82(13) . . . . ?
C34 C35 C36 C37 -0.04(13) . . . . ?
C34 C35 C36 C45 -179.97(7) . . . . ?
C35 C36 C37 C38 -0.30(13) . . . . ?
C36 C37 C38 C33 0.72(14) . . . . ?
C38 C33 C34 C35 0.49(13) . . . . ?
C39 C40 C41 C42 0.36(14) . . . . ?
C40 C39 C44 C43 0.69(13) . . . . ?
C40 C41 C42 O3 -177.40(10) . . . . ?
C40 C41 C42 O4 178.62(11) . . . . ?
C40 C41 C42 C43 0.95(15) . . . . ?
C41 C42 C43 C44 -1.43(15) . . . . ?
C42 O3 C46 C47 178.86(14) . . . . ?
C42 O4 C50 C48 173.20(15) . . . . ?
C42 C43 C44 C39 0.61(14) . . . . ?
C44 C39 C40 C41 -1.18(14) . . . . ?
C45 C36 C37 C38 179.63(8) . . . . ?
