#------------------------------------------------------------------------------
#$Date: 2025-12-02 04:11:17 +0100 (Tue 02 de Dec de 2025) $
#$Revision: 303996 $
#$URL: svn://www.crystallography.net/cod/cif/1/57/63/1576362.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_1576362
loop_
_publ_author_name
'Xia, Wen-Li'
'Ran, Xiaoyun'
'Zhao, Yu'
'Zhang, Hong'
'Zhou, Qian'
'Yu, Xiao-Qi'
'Li, Kun'
_publ_section_title
;
 Fine-Tuning J-Aggregation via Steric Hindrance for High-Efficiency NIR-II
 Bioimaging and Photothermal Therapy
;
_journal_name_full               'Materials Horizons'
_journal_paper_doi               10.1039/D5MH01966D
_journal_year                    2026
_chemical_formula_moiety         'C52 H30 N6, 1[C5H12O]'
_chemical_formula_sum            'C57 H42 N6 O'
_chemical_formula_weight         826.96
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-20
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-11-22 deposited with the CCDC.	2025-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.148(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.354(3)
_cell_length_b                   19.366(3)
_cell_length_c                   18.938(4)
_cell_measurement_reflns_used    5561
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.41
_cell_volume                     4485.1(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2025/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.1474
_diffrn_reflns_av_unetI/netI     0.1222
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34412
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.969
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3727
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1703 before and 0.1150 after correction.
The Ratio of minimum to maximum transmission is 0.4999.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7892
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0796
_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)+(0.1278P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4997
_reflns_number_total             7892
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5mh01966d3.cif
_cod_data_source_block           mo_lk_xwl_c_0m_a
_cod_original_cell_volume        4485.2(15)
_cod_database_code               1576362
_shelx_shelxl_version_number     2025/1
_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   0.997
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C15, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C56(H56), C57(H57), C3(H3), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36), C40(H40), C41(H41), C42(H42), C43(H43)
;
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.4667(2) 0.82465(13) 0.91625(13) 0.0367(7) Uani 1 1 d . . . . .
C2 C 0.4299(2) 0.75223(13) 0.73574(15) 0.0278(7) Uani 1 1 d . . . . .
N3 N 0.3378(2) 0.86245(12) 0.49510(14) 0.0377(7) Uani 1 1 d . . . . .
N4 N 0.6775(2) 0.46928(14) 0.52511(16) 0.0501(8) Uani 1 1 d . . . . .
N5 N 0.6681(2) 0.66636(15) 0.61686(17) 0.0542(9) Uani 1 1 d . . . . .
N6 N 0.1274(2) 0.46009(13) 0.79112(16) 0.0455(7) Uani 1 1 d . . . . .
N7 N 0.1977(2) 0.66682(14) 0.76365(17) 0.0505(8) Uani 1 1 d . . . . .
C56 C 0.5192(3) 0.75593(19) 1.1285(2) 0.0541(10) Uani 1 1 d . . . . .
H56 H 0.531279 0.739691 1.176284 0.065 Uiso 1 1 calc R U . . .
C57 C 0.4159(3) 0.7566(2) 1.0918(2) 0.0625(11) Uani 1 1 d . . . . .
H57 H 0.356554 0.741395 1.114592 0.075 Uiso 1 1 calc R U . . .
C3 C 0.3962(3) 0.7793(2) 1.02135(19) 0.0542(10) Uani 1 1 d . . . . .
H3 H 0.324175 0.779474 0.995863 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4842(2) 0.80175(15) 0.98931(16) 0.0354(8) Uani 1 1 d . . . . .
C5 C 0.4590(2) 0.77816(15) 0.86159(16) 0.0322(7) Uani 1 1 d . . . . .
C6 C 0.4395(2) 0.80070(14) 0.78911(16) 0.0314(7) Uani 1 1 d . . . . .
H6 H 0.433171 0.848497 0.778018 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4094(2) 0.75955(14) 0.65779(15) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.3830(2) 0.81498(14) 0.61448(16) 0.0310(7) Uani 1 1 d . . . . .
H8 H 0.377618 0.859600 0.634520 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3636(2) 0.80602(14) 0.53969(16) 0.0319(7) Uani 1 1 d . . . . .
C10 C 0.3465(3) 0.85754(15) 0.42060(18) 0.0384(8) Uani 1 1 d . . . . .
C11 C 0.2535(3) 0.8516(2) 0.3717(2) 0.0661(12) Uani 1 1 d . . . . .
H11 H 0.184363 0.852650 0.388211 0.079 Uiso 1 1 calc R U . . .
C12 C 0.2567(5) 0.8441(3) 0.3001(3) 0.1021(19) Uani 1 1 d . . . . .
H12 H 0.190943 0.839596 0.267707 0.123 Uiso 1 1 calc R U . . .
C13 C 0.3528(5) 0.8434(3) 0.2767(3) 0.0840(15) Uani 1 1 d . U . . .
H13 H 0.354923 0.838291 0.226993 0.101 Uiso 1 1 calc R U . . .
C14 C 0.4463(3) 0.8564(2) 0.3975(2) 0.0668(13) Uani 1 1 d . . . . .
H14 H 0.512011 0.860080 0.430023 0.080 Uiso 1 1 calc R U . . .
C15 C 0.4484(4) 0.8496(2) 0.3214(3) 0.0812(16) Uani 1 1 d . U . . .
H15 H 0.516067 0.849376 0.303089 0.097 Uiso 1 1 calc R U . . .
C16 C 0.2778(3) 0.91989(16) 0.51696(17) 0.0445(9) Uani 1 1 d . . . . .
C17 C 0.3091(4) 0.98601(19) 0.5030(2) 0.0738(14) Uani 1 1 d . . . . .
H17 H 0.372454 0.993500 0.480912 0.089 Uiso 1 1 calc R U . . .
C18 C 0.2486(6) 1.0416(2) 0.5211(3) 0.102(2) Uani 1 1 d . . . . .
H18 H 0.270329 1.087340 0.511576 0.123 Uiso 1 1 calc R U . . .
C19 C 0.1578(6) 1.0306(3) 0.5527(3) 0.104(2) Uani 1 1 d . . . . .
H19 H 0.115905 1.069025 0.564430 0.125 Uiso 1 1 calc R U . . .
C20 C 0.1257(4) 0.9654(3) 0.5679(2) 0.0815(15) Uani 1 1 d . . . . .
H20 H 0.063453 0.958716 0.591351 0.098 Uiso 1 1 calc R U . . .
C21 C 0.1844(3) 0.9088(2) 0.5489(2) 0.0564(10) Uani 1 1 d . . . . .
H21 H 0.161189 0.863220 0.557584 0.068 Uiso 1 1 calc R U . . .
C22 C 0.3707(3) 0.73967(15) 0.51045(16) 0.0342(7) Uani 1 1 d . . . . .
H22 H 0.359991 0.733715 0.460150 0.041 Uiso 1 1 calc R U . . .
C23 C 0.3935(2) 0.68263(14) 0.55497(16) 0.0316(7) Uani 1 1 d . . . . .
H23 H 0.395333 0.637633 0.535193 0.038 Uiso 1 1 calc R U . . .
C24 C 0.4132(2) 0.69182(13) 0.62774(15) 0.0282(7) Uani 1 1 d . . . . .
C25 C 0.4297(2) 0.64277(14) 0.68611(15) 0.0296(7) Uani 1 1 d . . . . .
C26 C 0.4424(2) 0.68033(14) 0.75126(15) 0.0303(7) Uani 1 1 d . . . . .
C27 C 0.4724(2) 0.70641(15) 0.87684(16) 0.0354(7) Uani 1 1 d . . . . .
H27 H 0.486841 0.691177 0.924938 0.042 Uiso 1 1 calc R U . . .
C28 C 0.4645(2) 0.65904(15) 0.82212(16) 0.0336(7) Uani 1 1 d . . . . .
H28 H 0.474126 0.611311 0.832804 0.040 Uiso 1 1 calc R U . . .
C29 C 0.6066(3) 0.77879(19) 1.0964(2) 0.0517(9) Uani 1 1 d . . . . .
H29 H 0.678529 0.778809 1.121994 0.062 Uiso 1 1 calc R U . . .
C30 C 0.5880(3) 0.80143(16) 1.02698(18) 0.0417(8) Uani 1 1 d . . . . .
H30 H 0.647696 0.817088 1.004642 0.050 Uiso 1 1 calc R U . . .
C31 C 0.4709(3) 0.89873(15) 0.90558(16) 0.0368(8) Uani 1 1 d . . . . .
C32 C 0.3895(3) 0.94020(16) 0.92722(17) 0.0405(8) Uani 1 1 d . . . . .
H32 H 0.330660 0.919903 0.947112 0.049 Uiso 1 1 calc R U . . .
C33 C 0.3949(3) 1.01072(18) 0.91960(18) 0.0466(9) Uani 1 1 d . . . . .
H33 H 0.339406 1.039189 0.934125 0.056 Uiso 1 1 calc R U . . .
C34 C 0.4808(3) 1.04036(17) 0.89081(18) 0.0482(9) Uani 1 1 d . . . . .
H34 H 0.484256 1.089053 0.885440 0.058 Uiso 1 1 calc R U . . .
C35 C 0.5620(3) 0.99864(17) 0.86984(19) 0.0490(9) Uani 1 1 d . . . . .
H35 H 0.620928 1.018885 0.849999 0.059 Uiso 1 1 calc R U . . .
C36 C 0.5573(3) 0.92745(16) 0.87775(18) 0.0426(8) Uani 1 1 d . . . . .
H36 H 0.613350 0.898914 0.864044 0.051 Uiso 1 1 calc R U . . .
C37 C 0.4242(2) 0.56853(14) 0.67862(15) 0.0289(7) Uani 1 1 d . . . . .
C38 C 0.3526(2) 0.52432(14) 0.71140(15) 0.0286(7) Uani 1 1 d . . . . .
C39 C 0.3715(2) 0.45259(14) 0.68799(16) 0.0324(7) Uani 1 1 d . . . . .
C40 C 0.3278(3) 0.38970(15) 0.70512(18) 0.0388(8) Uani 1 1 d . . . . .
H40 H 0.279791 0.387443 0.740066 0.047 Uiso 1 1 calc R U . . .
C41 C 0.3547(3) 0.33057(15) 0.6709(2) 0.0484(9) Uani 1 1 d . . . . .
H41 H 0.325806 0.287333 0.682864 0.058 Uiso 1 1 calc R U . . .
C42 C 0.4236(3) 0.33377(16) 0.6193(2) 0.0560(11) Uani 1 1 d . . . . .
H42 H 0.439473 0.292935 0.594898 0.067 Uiso 1 1 calc R U . . .
C43 C 0.4693(3) 0.39571(15) 0.60288(19) 0.0449(9) Uani 1 1 d . . . . .
H43 H 0.517190 0.397362 0.567869 0.054 Uiso 1 1 calc R U . . .
C44 C 0.4450(2) 0.45546(14) 0.63762(16) 0.0320(7) Uani 1 1 d . . . . .
C45 C 0.4843(2) 0.52749(14) 0.63441(15) 0.0289(7) Uani 1 1 d . . . . .
C46 C 0.5724(2) 0.54786(14) 0.60178(15) 0.0303(7) Uani 1 1 d . . . . .
C47 C 0.6293(2) 0.50307(15) 0.55973(17) 0.0364(8) Uani 1 1 d . . . . .
C48 C 0.6235(2) 0.61412(16) 0.61047(17) 0.0348(7) Uani 1 1 d . . . . .
C49 C 0.2668(2) 0.54321(14) 0.74705(15) 0.0296(7) Uani 1 1 d . . . . .
C50 C 0.1916(2) 0.49557(15) 0.77134(16) 0.0352(7) Uani 1 1 d . . . . .
C51 C 0.2316(2) 0.61269(15) 0.75579(17) 0.0354(8) 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'
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
C4 N1 C31 115.8(2) . . ?
C5 N1 C4 120.7(3) . . ?
C5 N1 C31 123.1(2) . . ?
C6 C2 C7 131.2(3) . . ?
C6 C2 C26 121.4(3) . . ?
C26 C2 C7 107.4(2) . . ?
C9 N3 C10 120.2(2) . . ?
C9 N3 C16 121.3(2) . . ?
C16 N3 C10 116.8(3) . . ?
C57 C56 H56 119.9 . . ?
C57 C56 C29 120.3(4) . . ?
C29 C56 H56 119.9 . . ?
C56 C57 H57 119.5 . . ?
C56 C57 C3 121.1(3) . . ?
C3 C57 H57 119.5 . . ?
C57 C3 H3 120.8 . . ?
C4 C3 C57 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 N1 119.8(3) . . ?
C30 C4 N1 120.1(3) . . ?
C30 C4 C3 120.2(3) . . ?
N1 C5 C6 120.8(3) . . ?
N1 C5 C27 119.7(3) . . ?
C27 C5 C6 119.5(3) . . ?
C2 C6 C5 119.0(3) . . ?
C2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C2 132.4(2) . . ?
C8 C7 C24 120.0(3) . . ?
C24 C7 C2 107.5(2) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.9(2) . . ?
C9 C8 H8 120.0 . . ?
N3 C9 C8 120.3(2) . . ?
N3 C9 C22 120.0(3) . . ?
C22 C9 C8 119.7(3) . . ?
C11 C10 N3 119.8(3) . . ?
C14 C10 N3 120.9(4) . . ?
C14 C10 C11 119.3(4) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 C10 122.5(4) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(6) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C15 122.1(5) . . ?
C15 C13 H13 119.0 . . ?
C10 C14 H14 121.2 . . ?
C10 C14 C15 117.6(4) . . ?
C15 C14 H14 121.2 . . ?
C13 C15 C14 119.5(4) . . ?
C13 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 N3 119.8(3) . . ?
C17 C16 C21 120.0(3) . . ?
C21 C16 N3 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(5) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(5) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 119.1(4) . . ?
C20 C21 H21 120.5 . . ?
C9 C22 H22 119.9 . . ?
C23 C22 C9 120.3(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.2 . . ?
C7 C24 C25 107.8(2) . . ?
C23 C24 C7 120.3(3) . . ?
C23 C24 C25 131.6(2) . . ?
C26 C25 C24 108.2(2) . . ?
C26 C25 C37 126.3(3) . . ?
C37 C25 C24 125.3(3) . . ?
C25 C26 C2 109.0(3) . . ?
C28 C26 C2 119.2(3) . . ?
C28 C26 C25 131.8(3) . . ?
C5 C27 H27 119.9 . . ?
C28 C27 C5 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C26 C28 H28 119.6 . . ?
C27 C28 C26 120.7(3) . . ?
C27 C28 H28 119.6 . . ?
C56 C29 H29 120.4 . . ?
C30 C29 C56 119.2(4) . . ?
C30 C29 H29 120.4 . . ?
C4 C30 H30 119.5 . . ?
C29 C30 C4 120.9(3) . . ?
C29 C30 H30 119.5 . . ?
C32 C31 N1 119.2(3) . . ?
C36 C31 N1 119.9(3) . . ?
C36 C31 C32 120.8(3) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 C31 119.6(3) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.1 . . ?
C33 C34 C35 119.8(3) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.9 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 119.3(3) . . ?
C31 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C38 C37 C25 125.1(2) . . ?
C38 C37 C45 108.9(2) . . ?
C45 C37 C25 126.0(2) . . ?
C37 C38 C39 107.2(2) . . ?
C49 C38 C37 128.0(2) . . ?
C49 C38 C39 123.8(2) . . ?
C40 C39 C38 131.8(2) . . ?
C40 C39 C44 120.1(3) . . ?
C44 C39 C38 108.0(2) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 C39 119.4(3) . . ?
C41 C40 H40 120.3 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.5(3) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 H42 119.7 . . ?
C43 C42 C41 120.6(3) . . ?
C43 C42 H42 119.7 . . ?
C42 C43 H43 120.1 . . ?
C42 C43 C44 119.8(3) . . ?
C44 C43 H43 120.1 . . ?
C39 C44 C45 108.1(2) . . ?
C43 C44 C39 119.5(3) . . ?
C43 C44 C45 132.4(2) . . ?
C37 C45 C44 107.4(2) . . ?
C46 C45 C37 127.4(2) . . ?
C46 C45 C44 124.7(2) . . ?
C45 C46 C47 123.8(3) . . ?
C45 C46 C48 124.6(2) . . ?
C47 C46 C48 111.4(2) . . ?
N4 C47 C46 177.2(3) . . ?
N5 C48 C46 177.5(3) . . ?
C38 C49 C50 124.3(2) . . ?
C38 C49 C51 124.9(2) . . ?
C50 C49 C51 110.3(2) . . ?
N6 C50 C49 176.4(3) . . ?
N7 C51 C49 176.0(3) . . ?
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 C4 1.440(4) . ?
N1 C5 1.365(4) . ?
N1 C31 1.451(4) . ?
C2 C6 1.372(4) . ?
C2 C7 1.469(4) . ?
C2 C26 1.427(4) . ?
N3 C9 1.390(4) . ?
N3 C10 1.433(4) . ?
N3 C16 1.430(4) . ?
N4 C47 1.151(3) . ?
N5 C48 1.150(4) . ?
N6 C50 1.152(4) . ?
N7 C51 1.146(4) . ?
C56 H56 0.9500 . ?
C56 C57 1.364(6) . ?
C56 C29 1.385(5) . ?
C57 H57 0.9500 . ?
C57 C3 1.392(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
C4 C30 1.377(5) . ?
C5 C6 1.428(4) . ?
C5 C27 1.424(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.362(4) . ?
C7 C24 1.433(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.413(4) . ?
C9 C22 1.407(4) . ?
C10 C11 1.375(5) . ?
C10 C14 1.366(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.326(7) . ?
C13 H13 0.9500 . ?
C13 C15 1.357(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.450(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(5) . ?
C16 C21 1.393(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.361(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.367(8) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.394(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(4) . ?
C24 C25 1.450(4) . ?
C25 C26 1.422(4) . ?
C25 C37 1.445(4) . ?
C26 C28 1.393(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.377(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.373(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(4) . ?
C31 C36 1.374(4) . ?
C32 H32 0.9500 . ?
C32 C33 1.376(5) . ?
C33 H33 0.9500 . ?
C33 C34 1.385(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(5) . ?
C35 H35 0.9500 . ?
C35 C36 1.389(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.434(4) . ?
C37 C45 1.435(4) . ?
C38 C39 1.487(4) . ?
C38 C49 1.384(4) . ?
C39 C40 1.389(4) . ?
C39 C44 1.409(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.379(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.386(5) . ?
C42 H42 0.9500 . ?
C42 C43 1.379(4) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(4) . ?
C44 C45 1.481(4) . ?
C45 C46 1.383(4) . ?
C46 C47 1.428(4) . ?
C46 C48 1.429(4) . ?
C49 C50 1.431(4) . ?
C49 C51 1.431(4) . ?
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 C4 C30 C29 -179.0(3) . . . . ?
N1 C5 C6 C2 -178.6(3) . . . . ?
N1 C5 C27 C28 179.8(3) . . . . ?
N1 C31 C32 C33 177.8(3) . . . . ?
N1 C31 C36 C35 -178.1(3) . . . . ?
C2 C7 C8 C9 -177.5(3) . . . . ?
C2 C7 C24 C23 178.0(2) . . . . ?
C2 C7 C24 C25 3.1(3) . . . . ?
C2 C26 C28 C27 1.1(4) . . . . ?
N3 C9 C22 C23 -178.1(3) . . . . ?
N3 C10 C11 C12 -177.5(4) . . . . ?
N3 C10 C14 C15 178.4(3) . . . . ?
N3 C16 C17 C18 177.1(4) . . . . ?
N3 C16 C21 C20 -178.2(4) . . . . ?
C56 C57 C3 C4 -0.4(6) . . . . ?
C56 C29 C30 C4 0.1(5) . . . . ?
C57 C56 C29 C30 -0.7(5) . . . . ?
C57 C3 C4 N1 179.1(3) . . . . ?
C57 C3 C4 C30 -0.2(5) . . . . ?
C3 C4 C30 C29 0.3(5) . . . . ?
C4 N1 C5 C6 178.7(2) . . . . ?
C4 N1 C5 C27 -2.3(4) . . . . ?
C4 N1 C31 C32 -67.5(4) . . . . ?
C4 N1 C31 C36 109.3(3) . . . . ?
C5 N1 C4 C3 -82.1(4) . . . . ?
C5 N1 C4 C30 97.2(3) . . . . ?
C5 N1 C31 C32 119.6(3) . . . . ?
C5 N1 C31 C36 -63.6(4) . . . . ?
C5 C27 C28 C26 -0.5(4) . . . . ?
C6 C2 C7 C8 -7.6(5) . . . . ?
C6 C2 C7 C24 177.0(3) . . . . ?
C6 C2 C26 C25 -179.3(2) . . . . ?
C6 C2 C26 C28 0.2(4) . . . . ?
C6 C5 C27 C28 -1.2(4) . . . . ?
C7 C2 C6 C5 179.6(3) . . . . ?
C7 C2 C26 C25 -0.5(3) . . . . ?
C7 C2 C26 C28 179.0(2) . . . . ?
C7 C8 C9 N3 -179.3(3) . . . . ?
C7 C8 C9 C22 0.6(4) . . . . ?
C7 C24 C25 C26 -3.4(3) . . . . ?
C7 C24 C25 C37 171.6(2) . . . . ?
C8 C7 C24 C23 1.9(4) . . . . ?
C8 C7 C24 C25 -173.0(2) . . . . ?
C8 C9 C22 C23 1.9(4) . . . . ?
C9 N3 C10 C11 104.8(4) . . . . ?
C9 N3 C10 C14 -73.1(4) . . . . ?
C9 N3 C16 C17 137.2(4) . . . . ?
C9 N3 C16 C21 -46.2(5) . . . . ?
C9 C22 C23 C24 -2.5(4) . . . . ?
C10 N3 C9 C8 163.4(3) . . . . ?
C10 N3 C9 C22 -16.5(4) . . . . ?
C10 N3 C16 C17 -57.7(5) . . . . ?
C10 N3 C16 C21 118.9(4) . . . . ?
C10 C11 C12 C13 -0.7(8) . . . . ?
C10 C14 C15 C13 -1.1(6) . . . . ?
C11 C10 C14 C15 0.5(5) . . . . ?
C11 C12 C13 C15 0.1(9) . . . . ?
C12 C13 C15 C14 0.8(8) . . . . ?
C14 C10 C11 C12 0.4(7) . . . . ?
C16 N3 C9 C8 -32.0(4) . . . . ?
C16 N3 C9 C22 148.1(3) . . . . ?
C16 N3 C10 C11 -60.5(4) . . . . ?
C16 N3 C10 C14 121.7(4) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C16 C21 C20 -1.6(6) . . . . ?
C17 C18 C19 C20 0.9(9) . . . . ?
C18 C19 C20 C21 -2.1(8) . . . . ?
C19 C20 C21 C16 2.4(7) . . . . ?
C21 C16 C17 C18 0.5(7) . . . . ?
C22 C23 C24 C7 0.6(4) . . . . ?
C22 C23 C24 C25 174.2(3) . . . . ?
C23 C24 C25 C26 -177.6(3) . . . . ?
C23 C24 C25 C37 -2.5(5) . . . . ?
C24 C7 C8 C9 -2.5(4) . . . . ?
C24 C25 C26 C2 2.4(3) . . . . ?
C24 C25 C26 C28 -177.0(3) . . . . ?
C24 C25 C37 C38 -122.7(3) . . . . ?
C24 C25 C37 C45 53.5(4) . . . . ?
C25 C26 C28 C27 -179.6(3) . . . . ?
C25 C37 C38 C39 178.4(3) . . . . ?
C25 C37 C38 C49 9.7(5) . . . . ?
C25 C37 C45 C44 -174.4(3) . . . . ?
C25 C37 C45 C46 13.4(5) . . . . ?
C26 C2 C6 C5 -1.9(4) . . . . ?
C26 C2 C7 C8 173.8(3) . . . . ?
C26 C2 C7 C24 -1.7(3) . . . . ?
C26 C25 C37 C38 51.5(5) . . . . ?
C26 C25 C37 C45 -132.3(3) . . . . ?
C27 C5 C6 C2 2.4(4) . . . . ?
C29 C56 C57 C3 0.8(6) . . . . ?
C31 N1 C4 C3 104.8(3) . . . . ?
C31 N1 C4 C30 -75.9(3) . . . . ?
C31 N1 C5 C6 -8.8(4) . . . . ?
C31 N1 C5 C27 170.2(3) . . . . ?
C31 C32 C33 C34 -0.2(5) . . . . ?
C32 C31 C36 C35 -1.3(5) . . . . ?
C32 C33 C34 C35 -0.2(5) . . . . ?
C33 C34 C35 C36 -0.1(5) . . . . ?
C34 C35 C36 C31 0.9(5) . . . . ?
C36 C31 C32 C33 1.0(5) . . . . ?
C37 C25 C26 C2 -172.6(3) . . . . ?
C37 C25 C26 C28 8.0(5) . . . . ?
C37 C38 C39 C40 177.5(3) . . . . ?
C37 C38 C39 C44 -5.2(3) . . . . ?
C37 C38 C49 C50 172.7(3) . . . . ?
C37 C38 C49 C51 2.0(5) . . . . ?
C37 C45 C46 C47 178.5(3) . . . . ?
C37 C45 C46 C48 3.9(5) . . . . ?
C38 C37 C45 C44 2.4(3) . . . . ?
C38 C37 C45 C46 -169.9(3) . . . . ?
C38 C39 C40 C41 175.3(3) . . . . ?
C38 C39 C44 C43 -174.6(3) . . . . ?
C38 C39 C44 C45 6.6(3) . . . . ?
C39 C38 C49 C50 5.8(5) . . . . ?
C39 C38 C49 C51 -164.9(3) . . . . ?
C39 C40 C41 C42 -0.8(6) . . . . ?
C39 C44 C45 C37 -5.6(3) . . . . ?
C39 C44 C45 C46 166.9(3) . . . . ?
C40 C39 C44 C43 3.1(5) . . . . ?
C40 C39 C44 C45 -175.7(3) . . . . ?
C40 C41 C42 C43 2.2(6) . . . . ?
C41 C42 C43 C44 -0.9(6) . . . . ?
C42 C43 C44 C39 -1.7(5) . . . . ?
C42 C43 C44 C45 176.7(4) . . . . ?
C43 C44 C45 C37 175.8(4) . . . . ?
C43 C44 C45 C46 -11.7(6) . . . . ?
C44 C39 C40 C41 -1.8(5) . . . . ?
C44 C45 C46 C47 7.6(5) . . . . ?
C44 C45 C46 C48 -167.1(3) . . . . ?
C45 C37 C38 C39 1.6(3) . . . . ?
C45 C37 C38 C49 -167.0(3) . . . . ?
C49 C38 C39 C40 -13.3(5) . . . . ?
C49 C38 C39 C44 164.1(3) . . . . ?
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 0.255 0.108 0.328 238.6 51.7 '1 C5H12O'
2 -0.255 -0.108 0.672 238.6 51.7 '1 C5H12O'
3 -0.245 0.392 0.828 238.6 51.7 '1 C5H12O'
4 0.245 0.608 0.172 238.6 51.7 '1 C5H12O'
