#------------------------------------------------------------------------------
#$Date: 2021-11-03 22:03:11 +0200 (Wed, 03 Nov 2021) $
#$Revision: 270227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519088.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_4519088
loop_
_publ_author_name
'Zhou, Pan-Ke'
'Zong, Lu-Lu'
'Song, Kai-Yue'
'Yang, Zhen-Cong'
'Li, Hao-Hong'
'Chen, Zhi-Rong'
_publ_section_title
;
 Embedding Azobenzol-Decorated Tetraphenylethylene into the Polymer Matrix
 to Implement a Ternary Memory Device with High Working
 Temperature/Humidity.
;
_journal_issue                   42
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              50350
_journal_page_last               50357
_journal_paper_doi               10.1021/acsami.1c14686
_journal_volume                  13
_journal_year                    2021
_chemical_formula_moiety         '0.5(C32 H24 N2)'
_chemical_formula_sum            'C16 H12 N'
_chemical_formula_weight         218.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 121.647(4)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   54.739(9)
_cell_length_b                   5.6219(8)
_cell_length_c                   36.439(6)
_cell_measurement_reflns_used    4154
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.290
_cell_measurement_theta_min      2.266
_cell_volume                     9546(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1202
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_h_min       -64
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            52740
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.051
_diffrn_reflns_theta_max         25.051
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0885 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.8588.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       needle
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.900
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         8426
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.2348
_refine_ls_R_factor_gt           0.1272
_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)+(0.1387P)²+60.4828P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3101
_refine_ls_wR_factor_ref         0.3748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3986
_reflns_number_total             8426
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am1c14686_si_002.cif
_cod_data_source_block           c2-c
_cod_database_code               4519088
_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   0.996
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C4-N2
 2.2 with sigma of 0.02
 N1-C7
 2.2 with sigma of 0.02
 C45-C46
 1.35 with sigma of 0.02
 C13-C14
 1.35 with sigma of 0.02
 C14-C21
 1.5 with sigma of 0.02
 C14-C15
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C45) \\sim Ueq, Uanis(C46) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.005
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.005
Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.002
Uanis(C20) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.01
Uanis(C30) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.02
Uanis(C13) = Uanis(C14)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
 C33(H33), C34(H34), C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43),
  C44(H44), C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C56(H56),
 C57(H57), C58(H58), C54(H54), C55(H55), C60(H60), C61(H61), C62(H62), C63(H63),
  C64(H64)
4.b Fitted hexagon refined as free rotating group:
 C56(C57,C58,C53,C54,C55)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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'
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
C1 C 0.80375(13) 0.1788(12) 0.7766(2) 0.0468(16) Uani 1 1 d . . . . .
H1 H 0.820528 0.164315 0.804497 0.056 Uiso 1 1 calc R U . . .
C2 C 0.79675(13) 0.0029(12) 0.7457(2) 0.0521(17) Uani 1 1 d . . . . .
H2 H 0.808779 -0.132582 0.752795 0.063 Uiso 1 1 calc R U . . .
C3 C 0.77266(14) 0.0227(13) 0.7051(2) 0.0531(18) Uani 1 1 d . . . . .
H3 H 0.767976 -0.096976 0.684053 0.064 Uiso 1 1 calc R U . . .
C4 C 0.75550(12) 0.2201(14) 0.6959(2) 0.0530(19) Uani 1 1 d D . . . .
C5 C 0.76191(13) 0.3951(12) 0.7259(2) 0.0516(17) Uani 1 1 d . . . . .
H5 H 0.749748 0.529659 0.718856 0.062 Uiso 1 1 calc R U . . .
C6 C 0.78617(14) 0.3736(13) 0.7665(2) 0.0537(18) Uani 1 1 d . . . . .
H6 H 0.790735 0.493774 0.787449 0.064 Uiso 1 1 calc R U . . .
C7 C 0.69292(15) 0.301(2) 0.5914(2) 0.081(3) Uani 1 1 d D . . . .
C8 C 0.68646(15) 0.1218(15) 0.5621(3) 0.067(2) Uani 1 1 d . . . . .
H8 H 0.698914 -0.011042 0.569468 0.080 Uiso 1 1 calc R U . . .
C9 C 0.66167(14) 0.1357(11) 0.5217(2) 0.0484(16) Uani 1 1 d . . . . .
H9 H 0.657200 0.013017 0.501150 0.058 Uiso 1 1 calc R U . . .
C10 C 0.64329(12) 0.3294(10) 0.51110(18) 0.0370(14) Uani 1 1 d . . . . .
C11 C 0.65116(14) 0.5070(12) 0.5418(2) 0.0508(17) Uani 1 1 d . . . . .
H11 H 0.639053 0.641793 0.535024 0.061 Uiso 1 1 calc R U . . .
C12 C 0.67559(17) 0.4942(16) 0.5813(2) 0.066(2) Uani 1 1 d . . . . .
H12 H 0.680524 0.618732 0.601609 0.080 Uiso 1 1 calc R U . . .
C13 C 0.6155(2) 0.3466(16) 0.4713(3) 0.125(3) Uani 1 1 d D . . . .
C14 C 0.6029(2) 0.3305(15) 0.4352(3) 0.125(3) Uani 1 1 d D U . . .
C15 C 0.62723(13) 0.2682(13) 0.4257(2) 0.0580(19) Uani 1 1 d D . . . .
C16 C 0.64795(12) 0.4219(12) 0.42954(18) 0.0428(16) Uani 1 1 d . . . . .
H16 H 0.652098 0.562172 0.446328 0.051 Uiso 1 1 calc R U . . .
C17 C 0.66265(19) 0.3758(17) 0.4096(3) 0.080(3) Uani 1 1 d . . . . .
H17 H 0.676396 0.487915 0.411966 0.096 Uiso 1 1 calc R U . . .
C18 C 0.6583(3) 0.181(2) 0.3872(3) 0.108(3) Uani 1 1 d . U . . .
H18 H 0.670362 0.146889 0.376236 0.129 Uiso 1 1 calc R U . . .
C19 C 0.6381(2) 0.0353(18) 0.3797(3) 0.096(3) Uani 1 1 d . U . . .
H19 H 0.633982 -0.094237 0.360565 0.115 Uiso 1 1 calc R U . . .
C20 C 0.62138(18) 0.0649(16) 0.4001(3) 0.090(3) Uani 1 1 d . U . . .
H20 H 0.607256 -0.047634 0.396138 0.109 Uiso 1 1 calc R U . . .
C21 C 0.57138(15) 0.3493(14) 0.4006(2) 0.077(3) Uani 1 1 d D . . . .
C22 C 0.56673(16) 0.4902(14) 0.3672(3) 0.068(2) Uani 1 1 d . . . . .
H22 H 0.581781 0.587733 0.369969 0.082 Uiso 1 1 calc R U . . .
C23 C 0.5400(3) 0.4926(18) 0.3289(3) 0.099(3) Uani 1 1 d . . . . .
H23 H 0.536451 0.597206 0.306117 0.119 Uiso 1 1 calc R U . . .
C24 C 0.5191(2) 0.342(2) 0.3247(4) 0.115(5) Uani 1 1 d . . . . .
H24 H 0.501059 0.338020 0.298420 0.138 Uiso 1 1 calc R U . . .
C25 C 0.5238(2) 0.202(2) 0.3567(4) 0.105(4) Uani 1 1 d . . . . .
H25 H 0.509147 0.097388 0.353350 0.126 Uiso 1 1 calc R U . . .
C26 C 0.5490(2) 0.2072(18) 0.3940(3) 0.103(4) Uani 1 1 d . . . . .
H26 H 0.551649 0.108060 0.416881 0.123 Uiso 1 1 calc R U . . .
C27 C 0.58626(16) 0.4231(13) 0.4839(2) 0.0592(19) Uani 1 1 d . . . . .
C28 C 0.5696(2) 0.6215(15) 0.4736(3) 0.097(3) Uani 1 1 d . U . . .
H28 H 0.567538 0.725164 0.451540 0.117 Uiso 1 1 calc R U . . .
C29 C 0.5555(2) 0.6725(19) 0.4958(5) 0.121(6) Uani 1 1 d . U . . .
H29 H 0.544174 0.812088 0.489303 0.146 Uiso 1 1 calc R U . . .
C30 C 0.5583(2) 0.522(2) 0.5262(5) 0.120(5) Uani 1 1 d . U . . .
H30 H 0.548697 0.556232 0.540945 0.144 Uiso 1 1 calc R U . . .
C31 C 0.57400(15) 0.3257(17) 0.5363(2) 0.068(2) Uani 1 1 d . . . . .
H31 H 0.575271 0.220999 0.557723 0.082 Uiso 1 1 calc R U . . .
C32 C 0.58840(12) 0.2748(12) 0.51581(18) 0.0440(16) Uani 1 1 d . . . . .
H32 H 0.599984 0.136052 0.523585 0.053 Uiso 1 1 calc R U . . .
C33 C 0.78917(14) 0.6602(13) 0.5023(2) 0.0560(18) Uani 1 1 d . . . . .
H33 H 0.805678 0.641772 0.530317 0.067 Uiso 1 1 calc R U . . .
C34 C 0.78595(13) 0.8615(13) 0.4783(2) 0.0566(19) Uani 1 1 d . . . . .
H34 H 0.800409 0.980594 0.489749 0.068 Uiso 1 1 calc R U . . .
C35 C 0.76192(13) 0.8896(14) 0.4381(2) 0.0561(19) Uani 1 1 d . . . . .
H35 H 0.759717 1.027667 0.421552 0.067 Uiso 1 1 calc R U . . .
C36 C 0.74098(13) 0.7163(15) 0.4217(2) 0.0565(19) Uani 1 1 d . . . . .
C37 C 0.74434(14) 0.5139(15) 0.4448(2) 0.065(2) Uani 1 1 d . . . . .
H37 H 0.730138 0.392677 0.432967 0.078 Uiso 1 1 calc R U . . .
C38 C 0.76836(15) 0.4868(14) 0.4853(2) 0.063(2) Uani 1 1 d . . . . .
H38 H 0.770575 0.347785 0.501584 0.075 Uiso 1 1 calc R U . . .
C39 C 0.6772(2) 0.802(2) 0.3203(2) 0.096(4) Uani 1 1 d . . . . .
C40 C 0.67626(13) 1.0025(17) 0.2978(2) 0.065(2) Uani 1 1 d . . . . .
H40 H 0.692322 1.106390 0.309468 0.079 Uiso 1 1 calc R U . . .
C41 C 0.65230(13) 1.0524(12) 0.25881(18) 0.0477(17) Uani 1 1 d . . . . .
H41 H 0.652065 1.187985 0.243058 0.057 Uiso 1 1 calc R U . . .
C42 C 0.62836(13) 0.9079(12) 0.2420(2) 0.0533(18) Uani 1 1 d . . . . .
C43 C 0.62969(17) 0.7082(13) 0.2649(3) 0.069(2) Uani 1 1 d . . . . .
H43 H 0.613460 0.606329 0.253436 0.082 Uiso 1 1 calc R U . . .
C44 C 0.6534(3) 0.6532(18) 0.3030(3) 0.094(3) Uani 1 1 d . . . . .
H44 H 0.653773 0.513653 0.318028 0.113 Uiso 1 1 calc R U . . .
C45 C 0.6037(2) 0.9616(14) 0.1979(4) 0.126(5) Uani 1 1 d D U . . .
C46 C 0.5811(2) 1.0100(14) 0.1778(3) 0.129(5) Uani 1 1 d D U . . .
C47 C 0.61388(13) 0.9908(11) 0.15928(19) 0.0448(16) Uani 1 1 d . . . . .
C48 C 0.63228(13) 0.8105(11) 0.16338(18) 0.0465(16) Uani 1 1 d . . . . .
H48 H 0.635231 0.678530 0.181544 0.056 Uiso 1 1 calc R U . . .
C49 C 0.64634(13) 0.8206(12) 0.1414(2) 0.0504(17) Uani 1 1 d . . . . .
H49 H 0.659016 0.695843 0.144534 0.060 Uiso 1 1 calc R U . . .
C50 C 0.64225(14) 1.0083(13) 0.1150(2) 0.0540(18) Uani 1 1 d . . . . .
H50 H 0.651900 1.013616 0.099696 0.065 Uiso 1 1 calc R U . . .
C51 C 0.62430(14) 1.1882(12) 0.1108(2) 0.0527(18) Uani 1 1 d . . . . .
H51 H 0.621651 1.319926 0.092765 0.063 Uiso 1 1 calc R U . . .
C52 C 0.60981(12) 1.1809(12) 0.1327(2) 0.0477(17) Uani 1 1 d . . . . .
H52 H 0.597156 1.306155 0.129411 0.057 Uiso 1 1 calc R U . . .
C56 C 0.54631(16) 1.0018(13) 0.2675(2) 0.136(5) Uani 1 1 d G . . . .
H56 H 0.537437 1.006700 0.283966 0.163 Uiso 1 1 calc R U . . .
C57 C 0.57050(15) 1.1394(11) 0.27965(15) 0.103(4) Uani 1 1 d G . . . .
H57 H 0.578161 1.238233 0.304423 0.124 Uiso 1 1 calc R U . . .
C58 C 0.58348(10) 1.1323(9) 0.25555(17) 0.076(2) Uani 1 1 d G . . . .
H58 H 0.600009 1.226269 0.263854 0.092 Uiso 1 1 calc R U . . .
C53 C 0.57226(10) 0.9876(9) 0.21930(15) 0.0536(18) Uani 1 1 d G . . . .
C54 C 0.54807(10) 0.8501(8) 0.20714(15) 0.063(2) Uani 1 1 d G . . . .
H54 H 0.540409 0.751238 0.182369 0.075 Uiso 1 1 calc R U . . .
C55 C 0.53509(11) 0.8572(11) 0.2312(2) 0.101(3) Uani 1 1 d G . . . .
H55 H 0.518561 0.763198 0.222938 0.122 Uiso 1 1 calc R U . . .
C59 C 0.55666(14) 1.0643(12) 0.13671(19) 0.0515(17) Uani 1 1 d . . . . .
C60 C 0.5413(2) 1.2664(14) 0.1324(3) 0.077(2) Uani 1 1 d . . . . .
H60 H 0.548096 1.371417 0.156233 0.093 Uiso 1 1 calc R U . . .
C61 C 0.5163(2) 1.3209(19) 0.0945(4) 0.099(4) Uani 1 1 d . . . . .
H61 H 0.506136 1.463010 0.091983 0.118 Uiso 1 1 calc R U . . .
C62 C 0.50632(17) 1.166(2) 0.0604(4) 0.110(4) Uani 1 1 d . . . . .
H62 H 0.489154 1.201452 0.033942 0.132 Uiso 1 1 calc R U . . .
C63 C 0.52070(18) 0.9651(19) 0.0644(2) 0.085(3) Uani 1 1 d . . . . .
H63 H 0.513289 0.856746 0.040936 0.102 Uiso 1 1 calc R U . . .
C64 C 0.54619(12) 0.9137(13) 0.10224(19) 0.0501(17) Uani 1 1 d . . . . .
H64 H 0.556468 0.773203 0.104275 0.060 Uiso 1 1 calc R U . . .
N1 N 0.72853(15) 0.1814(13) 0.6421(3) 0.105(3) Uani 1 1 d D . . . .
N2 N 0.71939(19) 0.3426(14) 0.6441(3) 0.115(4) Uani 1 1 d D . . . .
N3 N 0.71469(14) 0.8303(14) 0.3703(3) 0.087(2) Uani 1 1 d . . . . .
N4 N 0.7023(3) 0.6818(14) 0.3694(4) 0.136(4) 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 0.0033 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'
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
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C6 C1 C2 119.4(6) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(6) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.4(6) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 N1 104.0(6) . . ?
C5 C4 C3 121.7(6) . . ?
C5 C4 N1 134.3(6) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(6) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.2(7) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N2 134.0(9) . . ?
C12 C7 C8 121.2(6) . . ?
C12 C7 N2 104.7(9) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(7) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(6) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C13 123.7(7) . . ?
C11 C10 C9 117.7(6) . . ?
C11 C10 C13 118.4(7) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.1(7) . . ?
C12 C11 H11 118.9 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.3(7) . . ?
C11 C12 H12 120.4 . . ?
C10 C13 C27 110.0(7) . . ?
C14 C13 C10 147.3(14) . . ?
C14 C13 C27 102.7(10) . . ?
C13 C14 C15 101.7(10) . . ?
C13 C14 C21 134.5(13) . . ?
C21 C14 C15 123.7(8) . . ?
C16 C15 C14 125.7(6) . . ?
C16 C15 C20 117.9(7) . . ?
C20 C15 C14 113.7(7) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(7) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(10) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(11) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(9) . . ?
C20 C19 H19 119.3 . . ?
C15 C20 C19 116.5(8) . . ?
C15 C20 H20 121.7 . . ?
C19 C20 H20 121.7 . . ?
C22 C21 C14 112.5(7) . . ?
C22 C21 C26 116.8(7) . . ?
C26 C21 C14 128.7(8) . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.5(8) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.8(9) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(9) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(10) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 118.6 . . ?
C25 C26 C21 122.8(9) . . ?
C25 C26 H26 118.6 . . ?
C28 C27 C13 129.4(8) . . ?
C28 C27 C32 118.3(8) . . ?
C32 C27 C13 110.5(6) . . ?
C27 C28 H28 120.1 . . ?
C27 C28 C29 119.8(9) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 119.1(9) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 118.8 . . ?
C31 C30 C29 122.3(11) . . ?
C31 C30 H30 118.8 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.7(9) . . ?
C32 C31 H31 120.2 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.8(7) . . ?
C31 C32 H32 119.6 . . ?
C34 C33 H33 120.2 . . ?
C38 C33 H33 120.2 . . ?
C38 C33 C34 119.7(6) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 C33 120.2(7) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.6(7) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 N3 103.3(6) . . ?
C37 C36 C35 120.5(6) . . ?
C37 C36 N3 136.1(6) . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.7(7) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 C37 120.3(7) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C40 C39 C44 119.3(7) . . ?
C40 C39 N3 100.8(9) . . ?
C40 C39 N4 134.5(11) . . ?
C44 C39 N3 139.9(9) . . ?
C44 C39 N4 106.2(10) . . ?
N4 C39 N3 33.7(3) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.2(8) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 119.6 . . ?
C40 C41 C42 120.7(7) . . ?
C42 C41 H41 119.6 . . ?
C41 C42 C45 118.2(6) . . ?
C43 C42 C41 118.3(6) . . ?
C43 C42 C45 123.2(7) . . ?
C42 C43 H43 119.1 . . ?
C44 C43 C42 121.9(8) . . ?
C44 C43 H43 119.1 . . ?
C39 C44 H44 120.2 . . ?
C43 C44 C39 119.6(8) . . ?
C43 C44 H44 120.2 . . ?
C42 C45 C47 112.8(8) . . ?
C46 C45 C42 147.6(15) . . ?
C46 C45 C47 99.2(12) . . ?
C45 C46 C53 97.1(11) . . ?
C45 C46 C59 150.7(15) . . ?
C59 C46 C53 112.0(9) . . ?
C48 C47 C45 111.2(6) . . ?
C52 C47 C45 128.8(6) . . ?
C52 C47 C48 119.0(6) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 C47 120.5(6) . . ?
C49 C48 H48 119.8 . . ?
C48 C49 H49 119.8 . . ?
C50 C49 C48 120.5(6) . . ?
C50 C49 H49 119.8 . . ?
C49 C50 H50 120.1 . . ?
C51 C50 C49 119.8(6) . . ?
C51 C50 H50 120.1 . . ?
C50 C51 H51 119.7 . . ?
C50 C51 C52 120.6(6) . . ?
C52 C51 H51 119.7 . . ?
C47 C52 C51 119.7(6) . . ?
C47 C52 H52 120.2 . . ?
C51 C52 H52 120.2 . . ?
C57 C56 H56 120.0 . . ?
C57 C56 C55 120.0 . . ?
C55 C56 H56 120.0 . . ?
C56 C57 H57 120.0 . . ?
C56 C57 C58 120.0 . . ?
C58 C57 H57 120.0 . . ?
C57 C58 H58 120.0 . . ?
C53 C58 C57 120.0 . . ?
C53 C58 H58 120.0 . . ?
C58 C53 C46 124.9(4) . . ?
C58 C53 C54 120.0 . . ?
C54 C53 C46 113.5(4) . . ?
C53 C54 H54 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C54 C55 C56 120.0 . . ?
C54 C55 H55 120.0 . . ?
C60 C59 C46 118.7(7) . . ?
C64 C59 C46 122.9(7) . . ?
C64 C59 C60 118.1(6) . . ?
C59 C60 H60 119.1 . . ?
C59 C60 C61 121.8(8) . . ?
C61 C60 H60 119.1 . . ?
C60 C61 H61 120.6 . . ?
C60 C61 C62 118.7(9) . . ?
C62 C61 H61 120.6 . . ?
C61 C62 H62 119.9 . . ?
C63 C62 C61 120.3(8) . . ?
C63 C62 H62 119.9 . . ?
C62 C63 H63 119.6 . . ?
C62 C63 C64 120.8(9) . . ?
C64 C63 H63 119.6 . . ?
C59 C64 C63 120.3(7) . . ?
C59 C64 H64 119.9 . . ?
C63 C64 H64 119.9 . . ?
N2 N1 C4 88.1(9) . . ?
N1 N2 C7 87.6(9) . . ?
C36 N3 C39 148.0(7) . . ?
N4 N3 C36 84.2(10) . . ?
N4 N3 C39 63.8(9) . . ?
N3 N4 C39 82.5(9) . . ?
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
C1 H1 0.9500 . ?
C1 C2 1.393(9) . ?
C1 C6 1.374(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(9) . ?
C4 C5 1.374(10) . ?
C4 N1 1.741(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(12) . ?
C7 C12 1.359(12) . ?
C7 N2 1.710(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(8) . ?
C10 C11 1.390(8) . ?
C10 C13 1.453(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.357(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.124(10) . ?
C13 C27 1.931(15) . ?
C14 C15 1.582(12) . ?
C14 C21 1.515(10) . ?
C15 C16 1.373(9) . ?
C15 C20 1.403(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.363(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.312(13) . ?
C18 H18 0.9500 . ?
C18 C19 1.287(13) . ?
C19 H19 0.9500 . ?
C19 C20 1.459(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.359(10) . ?
C21 C26 1.372(11) . ?
C22 H22 0.9500 . ?
C22 C23 1.393(12) . ?
C23 H23 0.9500 . ?
C23 C24 1.366(15) . ?
C24 H24 0.9500 . ?
C24 C25 1.316(15) . ?
C25 H25 0.9500 . ?
C25 C26 1.336(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.362(11) . ?
C27 C32 1.385(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.411(15) . ?
C29 H29 0.9500 . ?
C29 C30 1.337(17) . ?
C30 H30 0.9500 . ?
C30 C31 1.325(14) . ?
C31 H31 0.9500 . ?
C31 C32 1.371(9) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C33 C34 1.383(9) . ?
C33 C38 1.375(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.372(8) . ?
C35 H35 0.9500 . ?
C35 C36 1.379(10) . ?
C36 C37 1.370(10) . ?
C36 N3 1.778(11) . ?
C37 H37 0.9500 . ?
C37 C38 1.375(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.377(14) . ?
C39 C44 1.394(14) . ?
C39 N3 1.905(12) . ?
C39 N4 1.724(13) . ?
C40 H40 0.9500 . ?
C40 C41 1.364(9) . ?
C41 H41 0.9500 . ?
C41 C42 1.382(8) . ?
C42 C43 1.377(9) . ?
C42 C45 1.490(11) . ?
C43 H43 0.9500 . ?
C43 C44 1.348(12) . ?
C44 H44 0.9500 . ?
C45 C46 1.087(10) . ?
C45 C47 1.774(15) . ?
C46 C53 1.820(14) . ?
C46 C59 1.423(10) . ?
C47 C48 1.381(9) . ?
C47 C52 1.379(9) . ?
C48 H48 0.9500 . ?
C48 C49 1.373(9) . ?
C49 H49 0.9500 . ?
C49 C50 1.364(9) . ?
C50 H50 0.9500 . ?
C50 C51 1.362(9) . ?
C51 H51 0.9500 . ?
C51 C52 1.390(9) . ?
C52 H52 0.9500 . ?
C56 H56 0.9500 . ?
C56 C57 1.3900 . ?
C56 C55 1.3900 . ?
C57 H57 0.9500 . ?
C57 C58 1.3900 . ?
C58 H58 0.9500 . ?
C58 C53 1.3900 . ?
C53 C54 1.3900 . ?
C54 H54 0.9500 . ?
C54 C55 1.3900 . ?
C55 H55 0.9500 . ?
C59 C60 1.373(10) . ?
C59 C64 1.367(9) . ?
C60 H60 0.9500 . ?
C60 C61 1.373(12) . ?
C61 H61 0.9500 . ?
C61 C62 1.374(15) . ?
C62 H62 0.9500 . ?
C62 C63 1.340(14) . ?
C63 H63 0.9500 . ?
C63 C64 1.383(10) . ?
C64 H64 0.9500 . ?
N1 N2 1.056(8) . ?
N3 N4 1.066(9) . ?
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
C1 C2 C3 C4 -0.4(10) . . . . ?
C2 C1 C6 C5 -0.4(9) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C2 C3 C4 N1 178.4(5) . . . . ?
C3 C4 C5 C6 0.2(10) . . . . ?
C3 C4 N1 N2 179.1(7) . . . . ?
C4 C5 C6 C1 0.0(10) . . . . ?
C4 N1 N2 C7 -179.6(4) . . . . ?
C5 C4 N1 N2 -2.8(10) . . . . ?
C6 C1 C2 C3 0.6(10) . . . . ?
C7 C8 C9 C10 -0.7(10) . . . . ?
C8 C7 C12 C11 1.4(11) . . . . ?
C8 C7 N2 N1 4.4(10) . . . . ?
C8 C9 C10 C11 1.6(9) . . . . ?
C8 C9 C10 C13 -173.4(7) . . . . ?
C9 C10 C11 C12 -1.0(9) . . . . ?
C9 C10 C13 C14 -49.2(19) . . . . ?
C9 C10 C13 C27 128.5(7) . . . . ?
C10 C11 C12 C7 -0.5(10) . . . . ?
C10 C13 C14 C15 -2.2(19) . . . . ?
C10 C13 C14 C21 175.8(10) . . . . ?
C11 C10 C13 C14 135.9(15) . . . . ?
C11 C10 C13 C27 -46.4(8) . . . . ?
C12 C7 C8 C9 -0.8(11) . . . . ?
C12 C7 N2 N1 -179.0(7) . . . . ?
C13 C10 C11 C12 174.2(7) . . . . ?
C13 C14 C15 C16 -71.3(10) . . . . ?
C13 C14 C15 C20 127.8(9) . . . . ?
C13 C14 C21 C22 132.4(12) . . . . ?
C13 C14 C21 C26 -64.0(17) . . . . ?
C13 C27 C28 C29 -162.1(8) . . . . ?
C13 C27 C32 C31 166.4(6) . . . . ?
C14 C15 C16 C17 -161.3(7) . . . . ?
C14 C15 C20 C19 162.7(7) . . . . ?
C14 C21 C22 C23 167.7(8) . . . . ?
C14 C21 C26 C25 -162.3(11) . . . . ?
C15 C14 C21 C22 -49.8(11) . . . . ?
C15 C14 C21 C26 113.7(11) . . . . ?
C15 C16 C17 C18 -2.2(12) . . . . ?
C16 C15 C20 C19 0.1(11) . . . . ?
C16 C17 C18 C19 6.6(15) . . . . ?
C17 C18 C19 C20 -7.5(16) . . . . ?
C18 C19 C20 C15 4.1(13) . . . . ?
C20 C15 C16 C17 -1.0(10) . . . . ?
C21 C14 C15 C16 110.4(9) . . . . ?
C21 C14 C15 C20 -50.6(11) . . . . ?
C21 C22 C23 C24 -3.4(14) . . . . ?
C22 C21 C26 C25 0.6(15) . . . . ?
C22 C23 C24 C25 2.1(16) . . . . ?
C23 C24 C25 C26 0.5(18) . . . . ?
C24 C25 C26 C21 -1.9(17) . . . . ?
C26 C21 C22 C23 2.0(13) . . . . ?
C27 C13 C14 C15 180.0(5) . . . . ?
C27 C13 C14 C21 -2.0(14) . . . . ?
C27 C28 C29 C30 -1.3(14) . . . . ?
C28 C27 C32 C31 0.4(10) . . . . ?
C28 C29 C30 C31 0.3(16) . . . . ?
C29 C30 C31 C32 1.0(14) . . . . ?
C30 C31 C32 C27 -1.4(11) . . . . ?
C32 C27 C28 C29 1.0(12) . . . . ?
C33 C34 C35 C36 0.2(10) . . . . ?
C34 C33 C38 C37 -0.5(11) . . . . ?
C34 C35 C36 C37 -1.7(11) . . . . ?
C34 C35 C36 N3 179.5(6) . . . . ?
C35 C36 C37 C38 2.1(11) . . . . ?
C35 C36 N3 C39 -171.4(8) . . . . ?
C35 C36 N3 N4 -173.2(7) . . . . ?
C36 C37 C38 C33 -1.0(11) . . . . ?
C36 N3 N4 C39 178.9(4) . . . . ?
C37 C36 N3 C39 10.1(14) . . . . ?
C37 C36 N3 N4 8.3(10) . . . . ?
C38 C33 C34 C35 0.9(11) . . . . ?
C39 C40 C41 C42 2.2(10) . . . . ?
C40 C39 C44 C43 -0.5(13) . . . . ?
C40 C39 N4 N3 -2.4(10) . . . . ?
C40 C41 C42 C43 -2.2(10) . . . . ?
C40 C41 C42 C45 -175.7(8) . . . . ?
C41 C42 C43 C44 0.8(11) . . . . ?
C41 C42 C45 C46 -119.0(16) . . . . ?
C41 C42 C45 C47 51.5(9) . . . . ?
C42 C43 C44 C39 0.5(12) . . . . ?
C42 C45 C46 C53 -7.0(18) . . . . ?
C42 C45 C46 C59 179.5(11) . . . . ?
C42 C45 C47 C48 45.3(8) . . . . ?
C42 C45 C47 C52 -123.0(7) . . . . ?
C43 C42 C45 C46 67.9(19) . . . . ?
C43 C42 C45 C47 -121.6(8) . . . . ?
C44 C39 C40 C41 -0.9(11) . . . . ?
C44 C39 N4 N3 179.9(8) . . . . ?
C45 C42 C43 C44 173.9(9) . . . . ?
C45 C46 C53 C58 64.9(8) . . . . ?
C45 C46 C53 C54 -129.5(7) . . . . ?
C45 C46 C59 C60 -129.8(18) . . . . ?
C45 C46 C59 C64 56(2) . . . . ?
C45 C47 C48 C49 -169.5(6) . . . . ?
C45 C47 C52 C51 167.3(6) . . . . ?
C46 C45 C47 C48 -139.8(7) . . . . ?
C46 C45 C47 C52 51.8(10) . . . . ?
C46 C53 C54 C55 -166.3(5) . . . . ?
C46 C59 C60 C61 -175.3(9) . . . . ?
C46 C59 C64 C63 173.5(9) . . . . ?
C47 C45 C46 C53 -178.0(4) . . . . ?
C47 C45 C46 C59 8(2) . . . . ?
C47 C48 C49 C50 -0.3(9) . . . . ?
C48 C47 C52 C51 -0.3(9) . . . . ?
C48 C49 C50 C51 0.6(10) . . . . ?
C49 C50 C51 C52 -0.8(10) . . . . ?
C50 C51 C52 C47 0.6(9) . . . . ?
C52 C47 C48 C49 0.1(9) . . . . ?
C56 C57 C58 C53 0.0 . . . . ?
C57 C56 C55 C54 0.0 . . . . ?
C57 C58 C53 C46 164.7(6) . . . . ?
C57 C58 C53 C54 0.0 . . . . ?
C58 C53 C54 C55 0.0 . . . . ?
C53 C46 C59 C60 57.0(9) . . . . ?
C53 C46 C59 C64 -116.9(7) . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C55 C56 C57 C58 0.0 . . . . ?
C59 C46 C53 C58 -118.5(6) . . . . ?
C59 C46 C53 C54 47.1(7) . . . . ?
C59 C60 C61 C62 1.1(13) . . . . ?
C60 C59 C64 C63 -0.4(11) . . . . ?
C60 C61 C62 C63 0.4(15) . . . . ?
C61 C62 C63 C64 -2.0(14) . . . . ?
C62 C63 C64 C59 2.0(12) . . . . ?
C64 C59 C60 C61 -1.1(12) . . . . ?
N1 C4 C5 C6 -177.7(6) . . . . ?
N2 C7 C8 C9 175.3(6) . . . . ?
N2 C7 C12 C11 -175.7(6) . . . . ?
N3 C36 C37 C38 -179.6(7) . . . . ?
N3 C39 C40 C41 -179.8(6) . . . . ?
N3 C39 C44 C43 177.8(7) . . . . ?
N4 C39 C40 C41 -178.4(7) . . . . ?
N4 C39 C44 C43 177.7(7) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.019 0.217 0.114 8.7 0.3 ?
2 0.019 0.217 0.386 8.7 0.3 ?
3 -0.019 0.783 0.614 8.7 0.3 ?
4 0.019 0.783 0.886 8.7 0.3 ?
5 0.099 0.119 0.315 14.7 0.4 ?
6 0.099 0.881 0.815 14.7 0.4 ?
7 0.401 0.381 0.685 14.7 0.4 ?
8 0.401 0.619 0.185 14.7 0.4 ?
9 0.481 0.283 0.614 8.7 0.3 ?
10 0.481 0.717 0.114 8.7 0.3 ?
11 0.519 0.283 0.886 8.7 0.3 ?
12 0.519 0.717 0.386 8.7 0.3 ?
13 0.599 0.381 0.815 14.7 0.4 ?
14 0.599 0.619 0.315 14.7 0.4 ?
15 0.901 0.119 0.185 14.7 0.4 ?
16 0.901 -0.119 0.685 14.7 0.4 ?
