#------------------------------------------------------------------------------
#$Date: 2024-01-06 10:17:57 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/99/1569909.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_1569909
loop_
_publ_author_name
'Fang, Lingyi'
'Zhang, Yuyan'
'Cai, Yaohang'
'Zhang, Jing'
'Wei, Yuefang'
'Yuan, Yi'
'Wang, Peng'
_publ_section_title
;
 Solution-processable organic semiconductors with over 220 °C glass
 transition temperature: manipulating morphology using a helical
 polycyclic heteroaromatic motif
;
_journal_issue                   11
_journal_name_full               'Energy & Environmental Science'
_journal_page_first              5231
_journal_page_last               5242
_journal_paper_doi               10.1039/D3EE02601A
_journal_volume                  16
_journal_year                    2023
_chemical_formula_moiety         'C39 H27 N3'
_chemical_formula_sum            'C39 H27 N3'
_chemical_formula_weight         537.63
_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_Hall           '-P 3'
_space_group_name_H-M_alt        'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-06 deposited with the CCDC.	2023-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            8
_cell_length_a                   19.8544(9)
_cell_length_b                   19.8544(9)
_cell_length_c                   16.6635(11)
_cell_measurement_reflns_used    6606
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      50.138
_cell_measurement_theta_min      3.213
_cell_volume                     5688.7(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1801
_diffrn_reflns_av_unetI/netI     0.1249
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            71060
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.104
_diffrn_reflns_theta_min         3.213
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1572 before and 0.1055 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7688
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1510
_refine_ls_R_factor_gt           0.0927
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1151P)²+3.5928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             7688
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ee02601a2.cif
_cod_data_source_block           230726_a_cl_0m
_cod_depositor_comments
'Adding full bibliography for 1569909--1569911.cif.'
_cod_original_cell_volume        5688.7(6)
_cod_database_code               1569909
_shelx_shelxl_version_number     2019/2
_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   0.986
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C21(H21), C22(H22), C25(H25),
 C26(H26), C27(H27), C28(H28), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38),
  C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46), C47(H47)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C29(H29A,H29B,H29C), C52(H52A,H52B,
 H52C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 206 electrons were 
found in a volume of 670Å³ in 3 voids per unit cell. 
This is consistent with the presence of 
0.375[C4H4O], 0.375[C4H4O] per Asymmetric Unit 
which account for 216 electrons 
per unit cell.
;
_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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
N1 N 0.63786(19) 0.57824(19) 0.64856(17) 0.0466(8) Uani 1 1 d . . . . .
C1 C 0.8718(3) 0.8266(3) 0.5673(3) 0.0663(12) Uani 1 1 d . . . . .
H1 H 0.905814 0.855542 0.524634 0.080 Uiso 1 1 calc R U . . .
N2 N 0.40959(19) 0.33006(19) 0.60520(17) 0.0473(8) Uani 1 1 d . . . . .
C2 C 0.8845(3) 0.8584(3) 0.6417(3) 0.0758(14) Uani 1 1 d . . . . .
H2 H 0.927366 0.909073 0.650670 0.091 Uiso 1 1 calc R U . . .
N3 N 0.59389(19) 0.45188(19) 0.39195(17) 0.0475(8) Uani 1 1 d . . . . .
C3 C 0.8353(3) 0.8173(3) 0.7051(3) 0.0705(13) Uani 1 1 d . . . . .
H3 H 0.844761 0.840571 0.756716 0.085 Uiso 1 1 calc R U . . .
C4 C 0.7741(3) 0.7446(3) 0.6944(3) 0.0578(11) Uani 1 1 d . . . . .
H4 H 0.740713 0.718028 0.738226 0.069 Uiso 1 1 calc R U . . .
C5 C 0.7592(2) 0.7072(3) 0.6170(2) 0.0542(10) Uani 1 1 d . . . . .
C6 C 0.8087(2) 0.7510(2) 0.5521(3) 0.0549(10) Uani 1 1 d . . . . .
C7 C 0.7930(3) 0.7200(3) 0.4734(3) 0.0589(11) Uani 1 1 d . . . . .
H7 H 0.825265 0.750768 0.430566 0.071 Uiso 1 1 calc R U . . .
C8 C 0.7329(2) 0.6474(3) 0.4574(2) 0.0532(10) Uani 1 1 d . . . . .
H8 H 0.723253 0.628425 0.403910 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6847(2) 0.6003(2) 0.5207(2) 0.0472(9) Uani 1 1 d . . . . .
C10 C 0.6968(2) 0.6309(2) 0.5982(2) 0.0477(9) Uani 1 1 d . . . . .
C11 C 0.6450(3) 0.5749(3) 0.7350(2) 0.0636(12) Uani 1 1 d . . . . .
H11A H 0.625779 0.606311 0.761098 0.095 Uiso 1 1 calc R U . . .
H11B H 0.699723 0.595365 0.749189 0.095 Uiso 1 1 calc R U . . .
H11C H 0.614276 0.520856 0.753098 0.095 Uiso 1 1 calc R U . . .
C12 C 0.5868(2) 0.5144(2) 0.6034(2) 0.0448(9) Uani 1 1 d . . . . .
C13 C 0.6168(2) 0.5236(2) 0.5242(2) 0.0439(9) Uani 1 1 d . . . . .
C14 C 0.5750(2) 0.4606(2) 0.4701(2) 0.0451(9) Uani 1 1 d . . . . .
C15 C 0.5036(2) 0.3945(2) 0.4912(2) 0.0434(9) Uani 1 1 d . . . . .
C16 C 0.4761(2) 0.3898(2) 0.5707(2) 0.0447(9) Uani 1 1 d . . . . .
C17 C 0.5141(2) 0.4507(2) 0.6264(2) 0.0444(9) Uani 1 1 d . . . . .
C18 C 0.6730(2) 0.4876(3) 0.3622(3) 0.0617(12) Uani 1 1 d . . . . .
H18A H 0.682070 0.447567 0.338648 0.093 Uiso 1 1 calc R U . . .
H18B H 0.709435 0.513014 0.406633 0.093 Uiso 1 1 calc R U . . .
H18C H 0.681072 0.526330 0.321232 0.093 Uiso 1 1 calc R U . . .
C19 C 0.5321(2) 0.3837(2) 0.3600(2) 0.0462(9) Uani 1 1 d . . . . .
C20 C 0.4746(2) 0.3479(2) 0.4192(2) 0.0445(9) Uani 1 1 d . . . . .
C21 C 0.4037(2) 0.2822(2) 0.3989(2) 0.0500(10) Uani 1 1 d . . . . .
H21 H 0.363294 0.258760 0.437596 0.060 Uiso 1 1 calc R U . . .
C22 C 0.3926(3) 0.2517(2) 0.3228(2) 0.0512(10) Uani 1 1 d . . . . .
H22 H 0.344347 0.207078 0.309727 0.061 Uiso 1 1 calc R U . . .
C23 C 0.4510(2) 0.2850(2) 0.2636(2) 0.0501(10) Uani 1 1 d . . . . .
C24 C 0.5240(2) 0.3533(2) 0.2804(2) 0.0503(10) Uani 1 1 d . . . . .
C25 C 0.5789(3) 0.3858(3) 0.2174(2) 0.0571(11) Uani 1 1 d . . . . .
H25 H 0.626401 0.432841 0.226232 0.068 Uiso 1 1 calc R U . . .
C26 C 0.5646(3) 0.3503(3) 0.1434(2) 0.0601(11) Uani 1 1 d . . . . .
H26 H 0.602607 0.372409 0.102234 0.072 Uiso 1 1 calc R U . . .
C27 C 0.4950(3) 0.2826(3) 0.1287(3) 0.0717(14) Uani 1 1 d . . . . .
H27 H 0.486002 0.258333 0.077609 0.086 Uiso 1 1 calc R U . . .
C28 C 0.4393(3) 0.2502(3) 0.1868(3) 0.0625(12) Uani 1 1 d . . . . .
H28 H 0.391943 0.203762 0.175620 0.075 Uiso 1 1 calc R U . . .
C29 C 0.3806(3) 0.2482(3) 0.5856(3) 0.0658(12) Uani 1 1 d . . . . .
H29A H 0.376666 0.219388 0.634840 0.099 Uiso 1 1 calc R U . . .
H29B H 0.416512 0.244159 0.548240 0.099 Uiso 1 1 calc R U . . .
H29C H 0.329119 0.226135 0.560719 0.099 Uiso 1 1 calc R U . . .
C30 C 0.4003(2) 0.3548(2) 0.6808(2) 0.0461(9) Uani 1 1 d . . . . .
C31 C 0.4628(2) 0.4292(2) 0.6952(2) 0.0448(9) Uani 1 1 d . . . . .
C32 C 0.4610(3) 0.4691(2) 0.7650(2) 0.0512(10) Uani 1 1 d . . . . .
H32 H 0.501222 0.520965 0.774950 0.061 Uiso 1 1 calc R U . . .
C33 C 0.4008(3) 0.4322(2) 0.8178(2) 0.0514(10) Uani 1 1 d . . . . .
H33 H 0.401144 0.459041 0.865112 0.062 Uiso 1 1 calc R U . . .
C34 C 0.3382(2) 0.3563(2) 0.8055(2) 0.0505(10) Uani 1 1 d . . . . .
C35 C 0.3353(2) 0.3159(2) 0.7335(2) 0.0510(10) Uani 1 1 d . . . . .
C36 C 0.2685(3) 0.2426(3) 0.7206(3) 0.0604(11) Uani 1 1 d . . . . .
H36 H 0.264446 0.214772 0.672802 0.072 Uiso 1 1 calc R U . . .
C37 C 0.2097(3) 0.2109(3) 0.7753(3) 0.0692(13) Uani 1 1 d . . . . .
H37 H 0.165423 0.161403 0.765011 0.083 Uiso 1 1 calc R U . . .
C38 C 0.2135(3) 0.2496(3) 0.8455(3) 0.0687(13) Uani 1 1 d . . . . .
H38 H 0.172283 0.226316 0.883345 0.082 Uiso 1 1 calc R U . . .
C39 C 0.2761(3) 0.3211(3) 0.8607(3) 0.0606(11) Uani 1 1 d . . . . .
H39 H 0.278002 0.347438 0.908908 0.073 Uiso 1 1 calc R U . . .
N4 N 0.76743(19) 0.49335(19) 0.91577(18) 0.0492(8) Uani 1 1 d . . . . .
C40 C 0.6909(3) 0.6960(3) 0.9292(2) 0.0643(12) Uani 1 1 d . . . . .
H40 H 0.649119 0.706467 0.930634 0.077 Uiso 1 1 calc R U . . .
C41 C 0.7654(3) 0.7566(3) 0.9264(3) 0.0705(13) Uani 1 1 d . . . . .
H41 H 0.775157 0.808606 0.925915 0.085 Uiso 1 1 calc R U . . .
C42 C 0.8280(3) 0.7421(3) 0.9242(3) 0.0686(13) Uani 1 1 d . . . . .
H42 H 0.879851 0.784533 0.922937 0.082 Uiso 1 1 calc R U . . .
C43 C 0.8150(3) 0.6677(3) 0.9239(3) 0.0636(12) Uani 1 1 d . . . . .
H43 H 0.857936 0.659005 0.923578 0.076 Uiso 1 1 calc R U . . .
C44 C 0.7377(3) 0.6028(2) 0.9241(2) 0.0512(10) Uani 1 1 d . . . . .
C45 C 0.6741(3) 0.6174(3) 0.9301(2) 0.0544(10) Uani 1 1 d . . . . .
C46 C 0.5979(3) 0.5560(3) 0.9382(2) 0.0579(11) Uani 1 1 d . . . . .
H46 H 0.556794 0.567035 0.943666 0.069 Uiso 1 1 calc R U . . .
C47 C 0.5810(3) 0.4801(3) 0.9385(2) 0.0561(11) Uani 1 1 d . . . . .
H47 H 0.528904 0.439581 0.946189 0.067 Uiso 1 1 calc R U . . .
C48 C 0.6403(2) 0.4617(2) 0.9275(2) 0.0463(9) Uani 1 1 d . . . . .
C49 C 0.7178(2) 0.5238(2) 0.9215(2) 0.0471(9) Uani 1 1 d . . . . .
C50 C 0.7218(2) 0.4127(2) 0.9208(2) 0.0459(9) Uani 1 1 d . . . . .
C51 C 0.6440(2) 0.3912(2) 0.9232(2) 0.0467(9) Uani 1 1 d . . . . .
C52 C 0.8406(3) 0.5319(3) 0.8722(3) 0.0662(12) Uani 1 1 d . . . . .
H52A H 0.837165 0.563243 0.828780 0.099 Uiso 1 1 calc R U . . .
H52B H 0.851469 0.492687 0.849586 0.099 Uiso 1 1 calc R U . . .
H52C H 0.882655 0.565588 0.908962 0.099 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 '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 N1 C11 124.6(3) . . ?
C12 N1 C10 108.4(3) . . ?
C12 N1 C11 122.7(3) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.1(5) . . ?
C6 C1 H1 119.5 . . ?
C16 N2 C29 122.4(3) . . ?
C16 N2 C30 108.1(3) . . ?
C30 N2 C29 122.9(3) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(5) . . ?
C3 C2 H2 119.7 . . ?
C14 N3 C18 123.6(3) . . ?
C14 N3 C19 108.4(3) . . ?
C19 N3 C18 123.7(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 C10 116.5(4) . . ?
C10 C5 C4 125.9(4) . . ?
C1 C6 C5 119.1(4) . . ?
C7 C6 C1 120.8(4) . . ?
C7 C6 C5 120.1(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C13 133.9(4) . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 C13 106.7(3) . . ?
N1 C10 C5 128.2(4) . . ?
N1 C10 C9 109.5(3) . . ?
C9 C10 C5 122.2(4) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 108.6(3) . . ?
N1 C12 C17 128.6(3) . . ?
C17 C12 C13 122.7(3) . . ?
C12 C13 C9 106.5(3) . . ?
C12 C13 C14 116.9(3) . . ?
C14 C13 C9 136.6(3) . . ?
N3 C14 C13 128.9(4) . . ?
N3 C14 C15 109.0(3) . . ?
C15 C14 C13 122.1(3) . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 C20 106.3(3) . . ?
C16 C15 C20 135.7(4) . . ?
N2 C16 C15 128.0(3) . . ?
N2 C16 C17 109.5(3) . . ?
C17 C16 C15 122.5(3) . . ?
C12 C17 C31 136.9(3) . . ?
C16 C17 C12 117.2(3) . . ?
C16 C17 C31 105.8(3) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 108.6(3) . . ?
N3 C19 C24 128.3(4) . . ?
C20 C19 C24 123.1(4) . . ?
C19 C20 C15 107.3(3) . . ?
C21 C20 C15 133.5(4) . . ?
C21 C20 C19 119.1(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.8(4) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 120.8(3) . . ?
C22 C23 C28 120.5(4) . . ?
C28 C23 C24 118.6(4) . . ?
C23 C24 C19 115.3(4) . . ?
C25 C24 C19 126.6(4) . . ?
C25 C24 C23 118.1(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.0(4) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(4) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(4) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 H28 119.5 . . ?
C27 C28 C23 121.0(4) . . ?
C27 C28 H28 119.5 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29B 109.5 . . ?
N2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N2 C30 C35 127.4(4) . . ?
C31 C30 N2 108.9(3) . . ?
C31 C30 C35 123.4(3) . . ?
C30 C31 C17 107.3(3) . . ?
C30 C31 C32 118.4(4) . . ?
C32 C31 C17 134.0(4) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 C31 119.2(4) . . ?
C33 C32 H32 120.4 . . ?
C32 C33 H33 118.3 . . ?
C32 C33 C34 123.3(4) . . ?
C34 C33 H33 118.3 . . ?
C33 C34 C35 119.2(4) . . ?
C33 C34 C39 121.4(4) . . ?
C39 C34 C35 119.3(4) . . ?
C30 C35 C34 116.3(4) . . ?
C36 C35 C30 126.4(4) . . ?
C36 C35 C34 117.3(4) . . ?
C35 C36 H36 119.3 . . ?
C37 C36 C35 121.5(4) . . ?
C37 C36 H36 119.3 . . ?
C36 C37 H37 119.6 . . ?
C36 C37 C38 120.9(5) . . ?
C38 C37 H37 119.6 . . ?
C37 C38 H38 119.9 . . ?
C39 C38 C37 120.3(4) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 H39 119.6 . . ?
C38 C39 C34 120.8(4) . . ?
C38 C39 H39 119.6 . . ?
C49 N4 C52 122.9(3) . . ?
C50 N4 C49 107.4(3) . . ?
C50 N4 C52 122.7(3) . . ?
C41 C40 H40 119.2 . . ?
C41 C40 C45 121.6(5) . . ?
C45 C40 H40 119.2 . . ?
C40 C41 H41 120.0 . . ?
C40 C41 C42 119.9(4) . . ?
C42 C41 H41 120.0 . . ?
C41 C42 H42 119.6 . . ?
C43 C42 C41 120.8(5) . . ?
C43 C42 H42 119.6 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C44 120.8(5) . . ?
C44 C43 H43 119.6 . . ?
C43 C44 C45 118.5(4) . . ?
C49 C44 C43 125.3(4) . . ?
C49 C44 C45 116.1(4) . . ?
C40 C45 C44 118.3(4) . . ?
C46 C45 C40 121.0(4) . . ?
C46 C45 C44 120.7(4) . . ?
C45 C46 H46 119.2 . . ?
C47 C46 C45 121.6(4) . . ?
C47 C46 H46 119.2 . . ?
C46 C47 H47 119.7 . . ?
C46 C47 C48 120.5(4) . . ?
C48 C47 H47 119.7 . . ?
C47 C48 C49 118.0(4) . . ?
C47 C48 C51 135.6(4) . . ?
C49 C48 C51 106.4(3) . . ?
N4 C49 C44 128.2(4) . . ?
N4 C49 C48 108.8(3) . . ?
C44 C49 C48 123.0(4) . . ?
N4 C50 C51 128.1(4) . 3_665 ?
C51 C50 N4 110.0(3) . . ?
C51 C50 C51 121.9(4) . 3_665 ?
C48 C51 C50 135.1(4) . 2_655 ?
C50 C51 C48 107.0(3) . . ?
C50 C51 C50 117.9(4) . 2_655 ?
N4 C52 H52A 109.5 . . ?
N4 C52 H52B 109.5 . . ?
N4 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
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 C10 1.394(5) . ?
N1 C11 1.452(5) . ?
N1 C12 1.384(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.357(7) . ?
C1 C6 1.417(6) . ?
N2 C16 1.384(5) . ?
N2 C29 1.465(5) . ?
N2 C30 1.397(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(7) . ?
N3 C14 1.390(5) . ?
N3 C18 1.450(5) . ?
N3 C19 1.401(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.355(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.443(6) . ?
C5 C6 1.427(6) . ?
C5 C10 1.432(6) . ?
C6 C7 1.415(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.361(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.416(6) . ?
C9 C10 1.396(5) . ?
C9 C13 1.445(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.422(5) . ?
C12 C17 1.415(5) . ?
C13 C14 1.424(5) . ?
C14 C15 1.413(5) . ?
C15 C16 1.417(5) . ?
C15 C20 1.448(5) . ?
C16 C17 1.409(5) . ?
C17 C31 1.449(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.404(5) . ?
C19 C24 1.433(5) . ?
C20 C21 1.401(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.374(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.409(6) . ?
C23 C24 1.433(6) . ?
C23 C28 1.416(6) . ?
C24 C25 1.416(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.376(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.366(7) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.396(6) . ?
C30 C35 1.426(6) . ?
C31 C32 1.418(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.365(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.409(6) . ?
C34 C35 1.429(6) . ?
C34 C39 1.410(6) . ?
C35 C36 1.413(6) . ?
C36 H36 0.9500 . ?
C36 C37 1.362(6) . ?
C37 H37 0.9500 . ?
C37 C38 1.380(7) . ?
C38 H38 0.9500 . ?
C38 C39 1.364(7) . ?
C39 H39 0.9500 . ?
N4 C49 1.394(5) . ?
N4 C50 1.393(5) . ?
N4 C52 1.454(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.364(7) . ?
C40 C45 1.424(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.410(7) . ?
C42 H42 0.9500 . ?
C42 C43 1.367(6) . ?
C43 H43 0.9500 . ?
C43 C44 1.428(6) . ?
C44 C45 1.432(6) . ?
C44 C49 1.413(6) . ?
C45 C46 1.396(6) . ?
C46 H46 0.9500 . ?
C46 C47 1.369(6) . ?
C47 H47 0.9500 . ?
C47 C48 1.408(6) . ?
C48 C49 1.414(6) . ?
C48 C51 1.440(6) . ?
C50 C51 1.382(6) . ?
C50 C51 1.447(6) 3_665 ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
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
N1 C12 C13 C9 -6.0(4) . . . . ?
N1 C12 C13 C14 175.4(3) . . . . ?
N1 C12 C17 C16 -175.1(4) . . . . ?
N1 C12 C17 C31 6.8(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C1 C6 C7 C8 179.8(4) . . . . ?
N2 C16 C17 C12 175.2(3) . . . . ?
N2 C16 C17 C31 -6.1(4) . . . . ?
N2 C30 C31 C17 -1.5(4) . . . . ?
N2 C30 C31 C32 173.3(3) . . . . ?
N2 C30 C35 C34 -176.0(4) . . . . ?
N2 C30 C35 C36 2.8(7) . . . . ?
C2 C1 C6 C5 -1.5(7) . . . . ?
C2 C1 C6 C7 176.1(5) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
N3 C14 C15 C16 176.3(3) . . . . ?
N3 C14 C15 C20 -6.0(4) . . . . ?
N3 C19 C20 C15 -2.0(4) . . . . ?
N3 C19 C20 C21 174.1(3) . . . . ?
N3 C19 C24 C23 -175.4(4) . . . . ?
N3 C19 C24 C25 1.6(7) . . . . ?
C3 C4 C5 C6 -3.0(6) . . . . ?
C3 C4 C5 C10 179.9(4) . . . . ?
C4 C5 C6 C1 3.1(6) . . . . ?
C4 C5 C6 C7 -174.5(4) . . . . ?
C4 C5 C10 N1 1.1(7) . . . . ?
C4 C5 C10 C9 177.4(4) . . . . ?
C5 C6 C7 C8 -2.6(6) . . . . ?
C6 C1 C2 C3 -0.4(8) . . . . ?
C6 C5 C10 N1 -176.0(4) . . . . ?
C6 C5 C10 C9 0.3(6) . . . . ?
C6 C7 C8 C9 -0.8(6) . . . . ?
C7 C8 C9 C10 3.9(6) . . . . ?
C7 C8 C9 C13 178.1(4) . . . . ?
C8 C9 C10 N1 173.3(3) . . . . ?
C8 C9 C10 C5 -3.6(6) . . . . ?
C8 C9 C13 C12 -169.6(4) . . . . ?
C8 C9 C13 C14 8.4(8) . . . . ?
C9 C13 C14 N3 6.9(7) . . . . ?
C9 C13 C14 C15 -172.8(4) . . . . ?
C10 N1 C12 C13 4.6(4) . . . . ?
C10 N1 C12 C17 -172.1(4) . . . . ?
C10 C5 C6 C1 -179.5(4) . . . . ?
C10 C5 C6 C7 2.8(6) . . . . ?
C10 C9 C13 C12 5.1(4) . . . . ?
C10 C9 C13 C14 -176.8(4) . . . . ?
C11 N1 C10 C5 -27.6(6) . . . . ?
C11 N1 C10 C9 155.8(4) . . . . ?
C11 N1 C12 C13 -153.0(4) . . . . ?
C11 N1 C12 C17 30.3(6) . . . . ?
C12 N1 C10 C5 175.3(4) . . . . ?
C12 N1 C10 C9 -1.3(4) . . . . ?
C12 C13 C14 N3 -175.2(4) . . . . ?
C12 C13 C14 C15 5.1(5) . . . . ?
C12 C17 C31 C30 -177.1(4) . . . . ?
C12 C17 C31 C32 9.3(8) . . . . ?
C13 C9 C10 N1 -2.4(4) . . . . ?
C13 C9 C10 C5 -179.3(3) . . . . ?
C13 C12 C17 C16 8.6(5) . . . . ?
C13 C12 C17 C31 -169.5(4) . . . . ?
C13 C14 C15 C16 -4.0(6) . . . . ?
C13 C14 C15 C20 173.7(3) . . . . ?
C14 N3 C19 C20 -1.8(4) . . . . ?
C14 N3 C19 C24 176.8(4) . . . . ?
C14 C15 C16 N2 -177.8(4) . . . . ?
C14 C15 C16 C17 5.1(6) . . . . ?
C14 C15 C20 C19 4.9(4) . . . . ?
C14 C15 C20 C21 -170.4(4) . . . . ?
C15 C16 C17 C12 -7.3(6) . . . . ?
C15 C16 C17 C31 171.4(3) . . . . ?
C15 C20 C21 C22 177.8(4) . . . . ?
C16 N2 C30 C31 -2.3(4) . . . . ?
C16 N2 C30 C35 172.2(4) . . . . ?
C16 C15 C20 C19 -178.0(4) . . . . ?
C16 C15 C20 C21 6.7(8) . . . . ?
C16 C17 C31 C30 4.6(4) . . . . ?
C16 C17 C31 C32 -169.0(4) . . . . ?
C17 C12 C13 C9 171.0(3) . . . . ?
C17 C12 C13 C14 -7.6(5) . . . . ?
C17 C31 C32 C33 176.7(4) . . . . ?
C18 N3 C14 C13 27.8(6) . . . . ?
C18 N3 C14 C15 -152.4(4) . . . . ?
C18 N3 C19 C20 155.6(4) . . . . ?
C18 N3 C19 C24 -25.9(6) . . . . ?
C19 N3 C14 C13 -174.8(4) . . . . ?
C19 N3 C14 C15 4.9(4) . . . . ?
C19 C20 C21 C22 3.0(6) . . . . ?
C19 C24 C25 C26 179.3(4) . . . . ?
C20 C15 C16 N2 5.3(7) . . . . ?
C20 C15 C16 C17 -171.8(4) . . . . ?
C20 C19 C24 C23 2.9(6) . . . . ?
C20 C19 C24 C25 179.9(4) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C21 C22 C23 C24 -1.3(6) . . . . ?
C21 C22 C23 C28 177.1(4) . . . . ?
C22 C23 C24 C19 0.0(5) . . . . ?
C22 C23 C24 C25 -177.3(4) . . . . ?
C22 C23 C28 C27 179.1(4) . . . . ?
C23 C24 C25 C26 -3.8(6) . . . . ?
C24 C19 C20 C15 179.4(4) . . . . ?
C24 C19 C20 C21 -4.5(6) . . . . ?
C24 C23 C28 C27 -2.5(6) . . . . ?
C24 C25 C26 C27 1.4(7) . . . . ?
C25 C26 C27 C28 0.6(7) . . . . ?
C26 C27 C28 C23 0.0(7) . . . . ?
C28 C23 C24 C19 -178.4(4) . . . . ?
C28 C23 C24 C25 4.3(6) . . . . ?
C29 N2 C16 C15 35.8(6) . . . . ?
C29 N2 C16 C17 -146.8(4) . . . . ?
C29 N2 C30 C31 149.7(4) . . . . ?
C29 N2 C30 C35 -35.8(6) . . . . ?
C30 N2 C16 C15 -172.0(4) . . . . ?
C30 N2 C16 C17 5.3(4) . . . . ?
C30 C31 C32 C33 3.6(5) . . . . ?
C30 C35 C36 C37 -180.0(4) . . . . ?
C31 C30 C35 C34 -2.3(6) . . . . ?
C31 C30 C35 C36 176.5(4) . . . . ?
C31 C32 C33 C34 -1.9(6) . . . . ?
C32 C33 C34 C35 -2.0(6) . . . . ?
C32 C33 C34 C39 -178.4(4) . . . . ?
C33 C34 C35 C30 3.9(5) . . . . ?
C33 C34 C35 C36 -175.0(4) . . . . ?
C33 C34 C39 C38 175.7(4) . . . . ?
C34 C35 C36 C37 -1.2(6) . . . . ?
C35 C30 C31 C17 -176.3(4) . . . . ?
C35 C30 C31 C32 -1.5(6) . . . . ?
C35 C34 C39 C38 -0.7(6) . . . . ?
C35 C36 C37 C38 0.0(7) . . . . ?
C36 C37 C38 C39 0.9(8) . . . . ?
C37 C38 C39 C34 -0.5(7) . . . . ?
C39 C34 C35 C30 -179.6(4) . . . . ?
C39 C34 C35 C36 1.5(6) . . . . ?
N4 C50 C51 C48 -5.5(4) . . . . ?
N4 C50 C51 C50 174.2(2) . . . 2_655 ?
C40 C41 C42 C43 0.8(7) . . . . ?
C40 C45 C46 C47 179.5(4) . . . . ?
C41 C40 C45 C44 -2.9(6) . . . . ?
C41 C40 C45 C46 175.8(4) . . . . ?
C41 C42 C43 C44 1.3(7) . . . . ?
C42 C43 C44 C45 -4.2(6) . . . . ?
C42 C43 C44 C49 178.1(4) . . . . ?
C43 C44 C45 C40 4.9(5) . . . . ?
C43 C44 C45 C46 -173.9(4) . . . . ?
C43 C44 C49 N4 -2.2(6) . . . . ?
C43 C44 C49 C48 175.3(4) . . . . ?
C44 C45 C46 C47 -1.8(6) . . . . ?
C45 C40 C41 C42 0.1(7) . . . . ?
C45 C44 C49 N4 -180.0(3) . . . . ?
C45 C44 C49 C48 -2.4(5) . . . . ?
C45 C46 C47 C48 -2.4(6) . . . . ?
C46 C47 C48 C49 4.0(5) . . . . ?
C46 C47 C48 C51 -178.9(4) . . . . ?
C47 C48 C49 N4 176.4(3) . . . . ?
C47 C48 C49 C44 -1.5(5) . . . . ?
C47 C48 C51 C50 7.2(7) . . . 2_655 ?
C47 C48 C51 C50 -173.1(4) . . . . ?
C49 N4 C50 C51 -175.5(3) . . . 3_665 ?
C49 N4 C50 C51 4.6(4) . . . . ?
C49 C44 C45 C40 -177.2(3) . . . . ?
C49 C44 C45 C46 4.1(5) . . . . ?
C49 C48 C51 C50 -175.4(4) . . . 2_655 ?
C49 C48 C51 C50 4.2(4) . . . . ?
C50 N4 C49 C44 176.0(3) . . . . ?
C50 N4 C49 C48 -1.8(4) . . . . ?
C51 C48 C49 N4 -1.5(4) . . . . ?
C51 C48 C49 C44 -179.4(3) . . . . ?
C51 C50 C51 C48 174.6(3) 3_665 . . . ?
C51 C50 C51 C50 -5.7(7) 3_665 . . 2_655 ?
C52 N4 C49 C44 -32.7(6) . . . . ?
C52 N4 C49 C48 149.5(4) . . . . ?
C52 N4 C50 C51 -146.8(4) . . . . ?
C52 N4 C50 C51 33.1(6) . . . 3_665 ?
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 0.000 0.000 0.000 235.8 100.2 '3 C4H4O'
2 0.000 0.000 0.500 20.1 6.4 ?
3 0.333 0.667 0.365 207.4 50.0 '1.5 C4H4O'
4 0.667 0.333 0.635 207.4 50.1 '1.5 C4H4O'
