#------------------------------------------------------------------------------
#$Date: 2023-04-04 13:03:34 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/83/1568355.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_1568355
loop_
_publ_author_name
'Mehra, Kundan Singh'
'Jha, Shivangee'
'Menon, Anila M.'
'Chopra, Deepak'
'Sankar, Jeyaraman'
_publ_section_title
;
 The deeper it goes, the brighter it glows: NIR emissive nitro-terrylene
 diimides with deep LUMOs.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3147
_journal_page_last               3153
_journal_paper_doi               10.1039/d2sc06162g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C58 H43 N5 O10'
_chemical_formula_sum            'C58 H43 N5 O10'
_chemical_formula_weight         969.97
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2022-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-30 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                100.242(6)
_cell_angle_beta                 95.440(6)
_cell_angle_gamma                96.856(7)
_cell_formula_units_Z            1
_cell_length_a                   8.7404(11)
_cell_length_b                   9.8973(14)
_cell_length_c                   15.641(2)
_cell_measurement_reflns_used    6974
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.36
_cell_volume                     1312.6(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1360
_diffrn_reflns_av_unetI/netI     0.2754
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16099
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         2.112
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.3872
_exptl_absorpt_correction_T_min  0.2333
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1317 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.6025.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear greenish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6375
_refine_ls_number_restraints     354
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.2968
_refine_ls_R_factor_gt           0.1396
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3880
_refine_ls_wR_factor_ref         0.4474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2044
_reflns_number_total             6375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           TDI_N3
_cod_depositor_comments
'Adding full bibliography for 1568354--1568358.cif.'
_cod_database_code               1568355
_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   0.994
_shelx_estimated_absorpt_t_min   0.978
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
3. Others
 Fixed Sof: N2(0.5) O3(0.5) O4(0.5) C19A(0.5) C20A(0.5) C14B(0.5) C18B(0.5)
 H18B(0.5) C19B(0.5) H19B(0.5) C20B(0.5) C14A(0.5) C18A(0.5) H18A(0.5)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C24(H24), C7(H7), C8(H8), C6(H6), C18B(H18B), C19B(H19B),
 C18A(H18A)
4.c Fitted hexagon refined as free rotating group:
 C15(C14B,C18B,C19B,C20B,C21)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C12(H12B,H12A,H12C), C11(H11A,H11B,H11C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_original_sample_id TDI_N3
_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
O2 O 0.7092(5) 0.3286(4) 0.1102(3) 0.0406(11) Uani 1 1 d . U . . .
N1 N 0.5294(6) 0.3272(5) 0.2044(3) 0.0356(8) Uani 1 1 d . U . . .
O1 O 0.3454(5) 0.3309(5) 0.2994(3) 0.0497(12) Uani 1 1 d . U . . .
O6 O 1.2451(5) 0.7156(5) 0.2963(4) 0.0521(13) Uani 1 1 d . U . . .
N3 N 1.1380(7) 0.7108(6) 0.2430(4) 0.0486(11) Uani 1 1 d . U . . .
C29 C 0.9556(7) 0.9386(6) 0.4728(4) 0.0343(11) Uani 1 1 d . U . . .
C28 C 0.9972(7) 1.1078(6) 0.6115(4) 0.0332(12) Uani 1 1 d . U . . .
C27 C 0.8826(7) 1.0258(6) 0.6405(4) 0.0334(10) Uani 1 1 d . U . . .
H27 H 0.858256 1.051864 0.698530 0.040 Uiso 1 1 calc R U . . .
C16 C 0.7522(7) 0.5124(6) 0.2326(4) 0.0344(9) Uani 1 1 d . U . . .
C22 C 0.9238(7) 0.7550(7) 0.3378(4) 0.0343(10) Uani 1 1 d . U . . .
C25 C 0.8264(7) 0.8708(6) 0.5025(4) 0.0347(8) Uani 1 1 d . U . . .
C26 C 0.8029(7) 0.9085(7) 0.5887(4) 0.0336(10) Uani 1 1 d . U . . .
H26 H 0.729598 0.851507 0.612661 0.040 Uiso 1 1 calc R U . . .
C13 C 0.4698(7) 0.3862(7) 0.2776(4) 0.0375(9) Uani 1 1 d . U . . .
O5 O 1.1473(6) 0.7203(6) 0.1664(4) 0.0731(15) Uani 1 1 d . U . . .
C1 C 0.4448(7) 0.1998(7) 0.1540(4) 0.0382(9) Uani 1 1 d . U . . .
C24 C 0.8897(7) 0.5659(7) 0.2108(5) 0.0377(10) Uani 1 1 d . U . . .
H24 H 0.927277 0.524201 0.158869 0.045 Uiso 1 1 calc R U . . .
C23 C 0.9763(7) 0.6828(7) 0.2651(5) 0.0398(9) Uani 1 1 d . U . . .
C9 C 0.3247(8) 0.2052(7) 0.0867(5) 0.0424(10) Uani 1 1 d . U . . .
C2 C 0.4876(7) 0.0739(7) 0.1687(4) 0.0405(10) Uani 1 1 d . U . . .
C17 C 0.6633(7) 0.3842(7) 0.1753(4) 0.0350(9) Uani 1 1 d . U . . .
C7 C 0.2927(8) -0.0444(7) 0.0548(5) 0.0428(11) Uani 1 1 d . U . . .
H7 H 0.240924 -0.129364 0.020444 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2498(8) 0.0786(7) 0.0393(5) 0.0433(11) Uani 1 1 d . U . . .
H8 H 0.166957 0.077245 -0.004944 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6216(7) 0.0697(7) 0.2397(5) 0.0434(11) Uani 1 1 d . U . . .
H3 H 0.646413 0.164893 0.276467 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4092(7) -0.0460(7) 0.1193(5) 0.0414(11) Uani 1 1 d . U . . .
H6 H 0.436024 -0.132375 0.129781 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2841(8) 0.3404(8) 0.0681(5) 0.0492(12) Uani 1 1 d . U . . .
H10 H 0.341384 0.417637 0.114243 0.059 Uiso 1 1 calc R U . . .
C5 C 0.7652(8) 0.0368(8) 0.2011(5) 0.0527(17) Uani 1 1 d . U . . .
H5A H 0.742507 -0.051902 0.159689 0.079 Uiso 1 1 calc R U . . .
H5B H 0.845571 0.030387 0.247711 0.079 Uiso 1 1 calc R U . . .
H5C H 0.801841 0.110205 0.170287 0.079 Uiso 1 1 calc R U . . .
C4 C 0.5757(8) -0.0279(8) 0.2999(5) 0.0547(17) Uani 1 1 d . U . . .
H4A H 0.487941 0.002119 0.329253 0.082 Uiso 1 1 calc R U . . .
H4B H 0.663782 -0.027121 0.343827 0.082 Uiso 1 1 calc R U . . .
H4C H 0.545722 -0.122003 0.265709 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3239(10) 0.3627(9) -0.0196(6) 0.0680(19) Uani 1 1 d . U . . .
H12B H 0.436307 0.367540 -0.020675 0.102 Uiso 1 1 calc R U . . .
H12A H 0.290691 0.449681 -0.030901 0.102 Uiso 1 1 calc R U . . .
H12C H 0.270737 0.285483 -0.064822 0.102 Uiso 1 1 calc R U . . .
C11 C 0.1132(9) 0.3480(9) 0.0647(6) 0.0708(19) Uani 1 1 d . U . . .
H11A H 0.056391 0.270302 0.021137 0.106 Uiso 1 1 calc R U . . .
H11B H 0.091716 0.435634 0.048409 0.106 Uiso 1 1 calc R U . . .
H11C H 0.079912 0.343070 0.122275 0.106 Uiso 1 1 calc R U . . .
N2 N 0.4743(12) 0.7895(12) 0.5069(7) 0.0381(11) Uani 0.5 1 d . U P A 1
O3 O 0.4127(11) 0.7294(10) 0.5550(7) 0.0515(19) Uani 0.5 1 d . U P A 1
O4 O 0.4616(10) 0.9053(10) 0.4994(6) 0.0425(18) Uani 0.5 1 d . U P A 1
C19A C 0.5657(15) 0.7079(14) 0.4437(9) 0.0365(9) Uani 0.5 1 d . U P A 1
C20A C 0.7159(15) 0.7623(14) 0.4403(9) 0.0358(9) Uani 0.5 1 d . U P A 1
C15 C 0.6965(6) 0.5765(5) 0.3100(3) 0.0340(8) Uani 1 1 d G U . . .
C14B C 0.5628(7) 0.5144(7) 0.3368(5) 0.0362(9) Uani 0.5 1 d G U P A 2
C18B C 0.5148(7) 0.5703(9) 0.4161(5) 0.0366(9) Uani 0.5 1 d G U P A 2
H18B H 0.423425 0.527907 0.434468 0.044 Uiso 0.5 1 calc R U P A 2
C19B C 0.6005(9) 0.6883(10) 0.4687(4) 0.0366(9) Uani 0.5 1 d G U P A 2
H19B H 0.567647 0.726486 0.522882 0.044 Uiso 0.5 1 calc R U P A 2
C20B C 0.7342(8) 0.7504(7) 0.4418(4) 0.0357(9) Uani 0.5 1 d G U P A 2
C21 C 0.7822(5) 0.6945(5) 0.3625(3) 0.0340(8) Uani 1 1 d G U . A .
C14A C 0.5551(15) 0.5220(15) 0.3287(10) 0.0361(9) Uani 0.5 1 d . U P A 1
C18A C 0.4827(15) 0.5902(14) 0.3952(9) 0.0365(9) Uani 0.5 1 d . U P A 1
H18A H 0.381410 0.556618 0.406195 0.044 Uiso 0.5 1 calc R U P A 1
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'
O O 0.0106 0.0060 '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
C13 N1 C1 117.2(6) . . ?
C13 N1 C17 124.1(6) . . ?
C17 N1 C1 118.7(5) . . ?
O6 N3 O5 124.9(6) . . ?
O6 N3 C23 120.3(7) . . ?
O5 N3 C23 114.7(6) . . ?
C28 C29 C29 117.6(8) 2_776 2_776 ?
C25 C29 C29 120.0(7) . 2_776 ?
C25 C29 C28 122.4(6) . 2_776 ?
C29 C28 C22 117.1(6) 2_776 2_776 ?
C27 C28 C29 118.8(6) . 2_776 ?
C27 C28 C22 124.1(6) . 2_776 ?
C28 C27 H27 118.9 . . ?
C26 C27 C28 122.2(6) . . ?
C26 C27 H27 118.9 . . ?
C24 C16 C17 119.1(6) . . ?
C24 C16 C15 119.6(6) . . ?
C15 C16 C17 121.3(6) . . ?
C23 C22 C28 124.1(6) . 2_776 ?
C23 C22 C21 116.3(6) . . ?
C21 C22 C28 119.5(5) . 2_776 ?
C29 C25 C20A 119.9(8) . . ?
C29 C25 C20B 117.6(6) . . ?
C26 C25 C29 118.7(6) . . ?
C26 C25 C20A 121.4(8) . . ?
C26 C25 C20B 123.3(6) . . ?
C27 C26 C25 121.3(7) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
N1 C13 C14B 118.8(6) . . ?
N1 C13 C14A 117.3(8) . . ?
O1 C13 N1 121.0(6) . . ?
O1 C13 C14B 120.0(6) . . ?
O1 C13 C14A 121.6(8) . . ?
C9 C1 N1 119.3(5) . . ?
C2 C1 N1 119.3(5) . . ?
C2 C1 C9 121.4(6) . . ?
C16 C24 H24 120.1 . . ?
C16 C24 C23 119.7(6) . . ?
C23 C24 H24 120.1 . . ?
C22 C23 N3 123.2(6) . . ?
C22 C23 C24 123.3(6) . . ?
C24 C23 N3 113.0(6) . . ?
C1 C9 C10 121.4(6) . . ?
C8 C9 C1 116.4(6) . . ?
C8 C9 C10 122.3(6) . . ?
C1 C2 C3 120.8(6) . . ?
C6 C2 C1 118.8(6) . . ?
C6 C2 C3 120.3(6) . . ?
O2 C17 N1 121.1(6) . . ?
O2 C17 C16 122.0(6) . . ?
N1 C17 C16 116.7(6) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(7) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 C9 121.5(6) . . ?
C7 C8 H8 119.2 . . ?
C2 C3 H3 107.1 . . ?
C5 C3 C2 111.9(6) . . ?
C5 C3 H3 107.1 . . ?
C5 C3 C4 111.2(6) . . ?
C4 C3 C2 112.3(6) . . ?
C4 C3 H3 107.1 . . ?
C2 C6 C7 121.2(6) . . ?
C2 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C11 112.6(7) . . ?
C12 C10 C9 111.7(6) . . ?
C12 C10 H10 109.3 . . ?
C12 C10 C11 104.6(7) . . ?
C11 C10 H10 109.3 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12B C12 H12A 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 N2 O4 125.5(12) . . ?
O3 N2 C19A 116.6(11) . . ?
O4 N2 C19A 117.6(12) . . ?
C20A C19A N2 117.5(12) . . ?
C18A C19A N2 113.8(11) . . ?
C18A C19A C20A 128.6(12) . . ?
C19A C20A C25 131.8(12) . . ?
C19A C20A C21 113.1(11) . . ?
C21 C20A C25 115.0(10) . . ?
C14B C15 C16 119.7(5) . . ?
C14B C15 C21 120.0 . . ?
C21 C15 C16 120.1(5) . . ?
C14A C15 C16 118.1(8) . . ?
C14A C15 C21 121.8(8) . . ?
C15 C14B C13 119.0(5) . . ?
C15 C14B C18B 120.0 . . ?
C18B C14B C13 121.0(5) . . ?
C14B C18B H18B 120.0 . . ?
C19B C18B C14B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B C18B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C19B C20B C25 117.9(5) . . ?
C19B C20B C21 120.0 . . ?
C21 C20B C25 122.0(5) . . ?
C22 C21 C20A 121.0(7) . . ?
C15 C21 C22 120.5(4) . . ?
C15 C21 C20A 118.3(7) . . ?
C20B C21 C22 119.4(4) . . ?
C20B C21 C15 120.0 . . ?
C15 C14A C13 121.9(11) . . ?
C15 C14A C18A 121.4(12) . . ?
C18A C14A C13 116.7(11) . . ?
C19A C18A C14A 115.7(13) . . ?
C19A C18A H18A 122.2 . . ?
C14A C18A H18A 122.2 . . ?
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
O2 C17 1.196(7) . ?
N1 C13 1.368(8) . ?
N1 C1 1.439(8) . ?
N1 C17 1.389(8) . ?
O1 C13 1.261(8) . ?
O6 N3 1.184(7) . ?
N3 O5 1.228(8) . ?
N3 C23 1.492(9) . ?
C29 C29 1.444(12) 2_776 ?
C29 C28 1.432(9) 2_776 ?
C29 C25 1.404(9) . ?
C28 C27 1.375(9) . ?
C28 C22 1.496(9) 2_776 ?
C27 H27 0.9500 . ?
C27 C26 1.362(8) . ?
C16 C24 1.353(9) . ?
C16 C17 1.498(9) . ?
C16 C15 1.420(8) . ?
C22 C23 1.379(9) . ?
C22 C21 1.427(8) . ?
C25 C26 1.376(9) . ?
C25 C20A 1.496(15) . ?
C25 C20B 1.482(8) . ?
C26 H26 0.9500 . ?
C13 C14B 1.524(8) . ?
C13 C14A 1.506(15) . ?
C1 C9 1.427(9) . ?
C1 C2 1.393(9) . ?
C24 H24 0.9500 . ?
C24 C23 1.397(9) . ?
C9 C8 1.390(9) . ?
C9 C10 1.495(9) . ?
C2 C3 1.546(9) . ?
C2 C6 1.362(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.370(9) . ?
C7 C6 1.367(9) . ?
C8 H8 0.9500 . ?
C3 H3 1.0000 . ?
C3 C5 1.489(10) . ?
C3 C4 1.510(10) . ?
C6 H6 0.9500 . ?
C10 H10 1.0000 . ?
C10 C12 1.494(11) . ?
C10 C11 1.501(10) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N2 O3 1.170(14) . ?
N2 O4 1.190(13) . ?
N2 C19A 1.512(16) . ?
C19A C20A 1.368(18) . ?
C19A C18A 1.356(17) . ?
C20A C21 1.484(15) . ?
C15 C14B 1.3900 . ?
C15 C21 1.3900 . ?
C15 C14A 1.367(16) . ?
C14B C18B 1.3900 . ?
C18B H18B 0.9500 . ?
C18B C19B 1.3900 . ?
C19B H19B 0.9500 . ?
C19B C20B 1.3900 . ?
C20B C21 1.3900 . ?
C14A C18A 1.384(18) . ?
C18A H18A 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
N1 C13 C14B C15 7.1(8) . . . . ?
N1 C13 C14B C18B -173.7(5) . . . . ?
N1 C13 C14A C15 -8.0(16) . . . . ?
N1 C13 C14A C18A 171.3(10) . . . . ?
N1 C1 C9 C8 178.7(6) . . . . ?
N1 C1 C9 C10 -0.5(10) . . . . ?
N1 C1 C2 C3 1.5(10) . . . . ?
N1 C1 C2 C6 -178.5(6) . . . . ?
O1 C13 C14B C15 -177.7(5) . . . . ?
O1 C13 C14B C18B 1.5(8) . . . . ?
O1 C13 C14A C15 174.3(10) . . . . ?
O1 C13 C14A C18A -6.4(15) . . . . ?
O6 N3 C23 C22 50.8(9) . . . . ?
O6 N3 C23 C24 -122.0(7) . . . . ?
C29 C29 C25 C26 -11.2(10) 2_776 . . . ?
C29 C29 C25 C20A 167.6(8) 2_776 . . . ?
C29 C29 C25 C20B 176.4(7) 2_776 . . . ?
C29 C28 C27 C26 -6.1(9) 2_776 . . . ?
C29 C25 C26 C27 12.9(9) . . . . ?
C29 C25 C20A C19A -160.1(13) . . . . ?
C29 C25 C20A C21 23.8(14) . . . . ?
C29 C25 C20B C19B -176.0(5) . . . . ?
C29 C25 C20B C21 7.7(8) . . . . ?
C28 C29 C25 C26 170.1(5) 2_776 . . . ?
C28 C29 C25 C20A -11.2(10) 2_776 . . . ?
C28 C29 C25 C20B -2.3(9) 2_776 . . . ?
C28 C27 C26 C25 -4.3(9) . . . . ?
C28 C22 C23 N3 18.0(10) 2_776 . . . ?
C28 C22 C23 C24 -170.0(6) 2_776 . . . ?
C28 C22 C21 C20A -3.0(11) 2_776 . . . ?
C28 C22 C21 C15 171.7(5) 2_776 . . . ?
C28 C22 C21 C20B -11.5(7) 2_776 . . . ?
C16 C24 C23 N3 167.7(6) . . . . ?
C16 C24 C23 C22 -5.1(10) . . . . ?
C16 C15 C14B C13 -6.1(6) . . . . ?
C16 C15 C14B C18B 174.7(5) . . . . ?
C16 C15 C21 C22 2.1(7) . . . . ?
C16 C15 C21 C20A 176.9(8) . . . . ?
C16 C15 C21 C20B -174.7(5) . . . . ?
C16 C15 C14A C13 9.1(16) . . . . ?
C16 C15 C14A C18A -170.2(10) . . . . ?
C22 C28 C27 C26 173.2(5) 2_776 . . . ?
C25 C20A C21 C22 -16.5(15) . . . . ?
C25 C20A C21 C15 168.7(6) . . . . ?
C25 C20B C21 C22 -0.6(7) . . . . ?
C25 C20B C21 C15 176.3(7) . . . . ?
C26 C25 C20A C19A 18.6(19) . . . . ?
C26 C25 C20A C21 -157.5(8) . . . . ?
C26 C25 C20B C19B 12.0(8) . . . . ?
C26 C25 C20B C21 -164.3(5) . . . . ?
C13 N1 C1 C9 88.2(8) . . . . ?
C13 N1 C1 C2 -95.3(7) . . . . ?
C13 N1 C17 O2 -179.1(5) . . . . ?
C13 N1 C17 C16 4.8(8) . . . . ?
C13 C14B C18B C19B -179.2(7) . . . . ?
C13 C14A C18A C19A 176.2(11) . . . . ?
O5 N3 C23 C22 -132.8(7) . . . . ?
O5 N3 C23 C24 54.4(8) . . . . ?
C1 N1 C13 O1 -0.3(9) . . . . ?
C1 N1 C13 C14B 174.9(6) . . . . ?
C1 N1 C13 C14A -178.0(7) . . . . ?
C1 N1 C17 O2 -0.6(8) . . . . ?
C1 N1 C17 C16 -176.7(5) . . . . ?
C1 C9 C8 C7 -1.9(11) . . . . ?
C1 C9 C10 C12 112.9(8) . . . . ?
C1 C9 C10 C11 -129.8(8) . . . . ?
C1 C2 C3 C5 -104.5(8) . . . . ?
C1 C2 C3 C4 129.7(7) . . . . ?
C1 C2 C6 C7 1.4(11) . . . . ?
C24 C16 C17 O2 -1.1(9) . . . . ?
C24 C16 C17 N1 174.9(6) . . . . ?
C24 C16 C15 C14B -173.9(5) . . . . ?
C24 C16 C15 C21 0.7(8) . . . . ?
C24 C16 C15 C14A 178.2(9) . . . . ?
C23 C22 C21 C20A 179.3(8) . . . . ?
C23 C22 C21 C15 -6.1(8) . . . . ?
C23 C22 C21 C20B 170.7(5) . . . . ?
C9 C1 C2 C3 177.9(7) . . . . ?
C9 C1 C2 C6 -2.0(11) . . . . ?
C2 C1 C9 C8 2.2(10) . . . . ?
C2 C1 C9 C10 -177.0(7) . . . . ?
C17 N1 C13 O1 178.3(6) . . . . ?
C17 N1 C13 C14B -6.6(9) . . . . ?
C17 N1 C13 C14A 0.5(10) . . . . ?
C17 N1 C1 C9 -90.4(7) . . . . ?
C17 N1 C1 C2 86.1(8) . . . . ?
C17 C16 C24 C23 -177.9(5) . . . . ?
C17 C16 C15 C14B 4.5(7) . . . . ?
C17 C16 C15 C21 179.2(5) . . . . ?
C17 C16 C15 C14A -3.3(11) . . . . ?
C8 C9 C10 C12 -66.3(9) . . . . ?
C8 C9 C10 C11 51.1(10) . . . . ?
C8 C7 C6 C2 -1.2(11) . . . . ?
C3 C2 C6 C7 -178.5(7) . . . . ?
C6 C2 C3 C5 75.5(9) . . . . ?
C6 C2 C3 C4 -50.4(9) . . . . ?
C6 C7 C8 C9 1.4(11) . . . . ?
C10 C9 C8 C7 177.3(7) . . . . ?
N2 C19A C20A C25 18(2) . . . . ?
N2 C19A C20A C21 -165.7(10) . . . . ?
N2 C19A C18A C14A 171.8(12) . . . . ?
O3 N2 C19A C20A -128.1(14) . . . . ?
O3 N2 C19A C18A 54.0(15) . . . . ?
O4 N2 C19A C20A 57.3(16) . . . . ?
O4 N2 C19A C18A -120.6(13) . . . . ?
C19A C20A C21 C22 166.6(9) . . . . ?
C19A C20A C21 C15 -8.1(16) . . . . ?
C20A C25 C26 C27 -165.8(8) . . . . ?
C20A C19A C18A C14A -6(2) . . . . ?
C15 C16 C24 C23 0.6(9) . . . . ?
C15 C16 C17 O2 -179.6(6) . . . . ?
C15 C16 C17 N1 -3.6(8) . . . . ?
C15 C14B C18B C19B 0.0 . . . . ?
C15 C14A C18A C19A -4.5(19) . . . . ?
C14B C15 C21 C22 176.8(5) . . . . ?
C14B C15 C21 C20B 0.0 . . . . ?
C14B C18B C19B C20B 0.0 . . . . ?
C18B C19B C20B C25 -176.4(7) . . . . ?
C18B C19B C20B C21 0.0 . . . . ?
C19B C20B C21 C22 -176.8(5) . . . . ?
C19B C20B C21 C15 0.0 . . . . ?
C20B C25 C26 C27 -175.1(6) . . . . ?
C21 C22 C23 N3 -164.4(6) . . . . ?
C21 C22 C23 C24 7.7(9) . . . . ?
C21 C15 C14B C13 179.3(7) . . . . ?
C21 C15 C14B C18B 0.0 . . . . ?
C21 C15 C14A C13 -173.5(7) . . . . ?
C21 C15 C14A C18A 7.2(18) . . . . ?
C14A C15 C21 C22 -175.3(9) . . . . ?
C14A C15 C21 C20A -0.5(14) . . . . ?
C18A C19A C20A C25 -164.3(13) . . . . ?
C18A C19A C20A C21 12(2) . . . . ?
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 0.500 0.500 171.3 46.0 '1 TOLUENE'
2 0.459 0.650 0.167 15.4 0.0 ?
3 0.541 0.350 0.833 15.4 0.0 ?
