#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:27:55 +0300 (Fri, 05 May 2023) $
#$Revision: 283486 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159197.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_7159197
loop_
_publ_author_name
'Singh, Gurdeep'
'Sharma, Sonam'
'Pandey, Rajat'
'Rekha, ?'
'Vijaya Anand, Ramasamy'
_publ_section_title
;
 Construction of heterocycle-fused tetrahydrocarbazoles through a formal
 [3 + 3]-annulation of 2-indolylmethanols with para-quinone
 methides.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2493
_journal_page_last               2498
_journal_paper_doi               10.1039/d3ob00124e
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C45 H42 F N2 O'
_chemical_formula_sum            'C45 H43 F N2 O'
_chemical_formula_weight         646.81
_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     dual
_audit_creation_date             2022-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-08-02 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                109.155(4)
_cell_angle_beta                 106.362(4)
_cell_angle_gamma                90.359(4)
_cell_formula_units_Z            2
_cell_length_a                   10.7970(5)
_cell_length_b                   11.7144(5)
_cell_length_c                   17.2757(7)
_cell_measurement_reflns_used    6391
_cell_measurement_temperature    298.01(1)
_cell_measurement_theta_max      27.4790
_cell_measurement_theta_min      2.6340
_cell_volume                     1968.69(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.01(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 119.00   0.50   10.00    --   29.89  54.00  60.00  376
  2  ω    -69.00 119.00   0.50   10.00    --   29.89  54.00-150.00  376
  3  ω    -69.00 119.00   0.50   10.00    --   29.89  54.00 120.00  376
  4  ω    -68.00 -39.00   0.50   10.00    --   29.89  54.00  60.00   58
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0205883000
_diffrn_orient_matrix_UB_12      -0.0334779000
_diffrn_orient_matrix_UB_13      -0.0447048000
_diffrn_orient_matrix_UB_21      -0.0202470000
_diffrn_orient_matrix_UB_22      0.0533111000
_diffrn_orient_matrix_UB_23      -0.0084922000
_diffrn_orient_matrix_UB_31      0.0625359000
_diffrn_orient_matrix_UB_32      0.0139781000
_diffrn_orient_matrix_UB_33      -0.0023880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29730
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.741
_diffrn_reflns_theta_min         2.558
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.091
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         13262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0804
_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)+(0.1312P)²+0.2017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2270
_refine_ls_wR_factor_ref         0.2817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6503
_reflns_number_total             13262
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00124e2.cif
_cod_data_source_block           xx-gs-40-rt
_cod_depositor_comments
'Adding full bibliography for 7159197--7159199.cif.'
_cod_database_code               7159197
_shelx_shelxl_version_number     2014/7
_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   0.993
_shelx_estimated_absorpt_t_min   0.993
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C7(H7), C21(H21), C35(H35), C29(H29), C18(H18), C46(H46),
 C20(H20), C39(H39), C32(H32), C19(H19), C30(H30), C37(H37), C38(H38), C36(H36),
  C45(H45), C42(H42), C44(H44), C43(H43)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C),
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.824
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
N1 N 0.13757(17) 0.73284(15) 0.52170(11) 0.0478(4) Uani 1 1 d . . . . .
O1 O 0.51833(17) 0.38814(17) 0.84429(12) 0.0718(5) Uani 1 1 d . . . . .
F1 F 0.88321(17) 1.12815(18) 0.99658(12) 0.1015(6) Uani 1 1 d . . . . .
N2 N 0.47103(17) 1.03034(16) 0.77334(11) 0.0516(4) Uani 1 1 d . . . . .
H2 H 0.4358 1.0972 0.7840 0.062 Uiso 1 1 calc R U . . .
C16 C 0.33533(19) 0.69060(17) 0.58846(12) 0.0431(4) Uani 1 1 d . . . . .
C9 C 0.58458(19) 0.55189(18) 0.71244(13) 0.0454(4) Uani 1 1 d . . . . .
H9 H 0.6475 0.5586 0.6864 0.054 Uiso 1 1 calc R U . . .
C26 C 0.41671(19) 0.92337(18) 0.70624(13) 0.0441(4) Uani 1 1 d . . . . .
C24 C 0.25668(19) 0.78152(18) 0.58463(12) 0.0432(4) Uani 1 1 d . . . . .
C28 C 0.6136(2) 0.8916(2) 0.78214(14) 0.0489(5) Uani 1 1 d . . . . .
C8 C 0.47929(19) 0.61881(17) 0.70194(12) 0.0428(4) Uani 1 1 d . . . . .
C15 C 0.46887(19) 0.70547(18) 0.65095(13) 0.0443(4) Uani 1 1 d . . . . .
H15 H 0.5317 0.6872 0.6184 0.053 Uiso 1 1 calc R U . . .
C27 C 0.49986(19) 0.83613(18) 0.70983(13) 0.0443(4) Uani 1 1 d . . . . .
C7 C 0.38629(19) 0.60827(18) 0.74118(12) 0.0443(4) Uani 1 1 d . . . . .
H7 H 0.3160 0.6534 0.7346 0.053 Uiso 1 1 calc R U . . .
C2 C 0.39308(19) 0.53340(18) 0.78982(12) 0.0431(4) Uani 1 1 d . . . . .
C10 C 0.59944(19) 0.47503(18) 0.76056(13) 0.0438(4) Uani 1 1 d . . . . .
C17 C 0.2644(2) 0.57972(18) 0.52443(12) 0.0456(4) Uani 1 1 d . . . . .
C25 C 0.28856(19) 0.91551(17) 0.63933(13) 0.0432(4) Uani 1 1 d . . . . .
C40 C 0.3095(2) 0.99301(18) 0.58569(13) 0.0470(4) Uani 1 1 d . . . . .
C1 C 0.50109(19) 0.46620(18) 0.79844(13) 0.0449(4) Uani 1 1 d . . . . .
C22 C 0.1419(2) 0.60917(18) 0.48488(13) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.2832(2) 0.5222(2) 0.82965(13) 0.0488(5) Uani 1 1 d . . . . .
C41 C 0.1804(2) 0.95609(19) 0.68253(14) 0.0482(5) Uani 1 1 d . . . . .
C11 C 0.7197(2) 0.4049(2) 0.77311(15) 0.0534(5) Uani 1 1 d . . . . .
C33 C 0.5906(2) 1.0124(2) 0.82026(14) 0.0507(5) Uani 1 1 d . . . . .
C21 C 0.0464(2) 0.5218(2) 0.42125(14) 0.0566(5) Uani 1 1 d . . . . .
H21 H -0.0349 0.5421 0.3968 0.068 Uiso 1 1 calc R U . . .
C35 C 0.3145(2) 0.9401(2) 0.50205(15) 0.0559(5) Uani 1 1 d . . . . .
H35 H 0.2998 0.8560 0.4760 0.067 Uiso 1 1 calc R U . . .
C29 C 0.7318(2) 0.8531(2) 0.81817(16) 0.0587(6) Uani 1 1 d . . . . .
H29 H 0.7503 0.7743 0.7936 0.070 Uiso 1 1 calc R U . . .
C18 C 0.2924(2) 0.4593(2) 0.49699(15) 0.0563(5) Uani 1 1 d . . . . .
H18 H 0.3726 0.4374 0.5218 0.068 Uiso 1 1 calc R U . . .
C46 C 0.1611(2) 0.9001(2) 0.73808(16) 0.0626(6) Uani 1 1 d . . . . .
H46 H 0.2178 0.8458 0.7525 0.075 Uiso 1 1 calc R U . . .
C20 C 0.0769(3) 0.4041(2) 0.39589(16) 0.0647(6) Uani 1 1 d . . . . .
H20 H 0.0147 0.3437 0.3535 0.078 Uiso 1 1 calc R U . . .
C39 C 0.3339(3) 1.1192(2) 0.62221(16) 0.0620(6) Uani 1 1 d . . . . .
H39 H 0.3327 1.1573 0.6784 0.074 Uiso 1 1 calc R U . . .
C32 C 0.6791(2) 1.0947(2) 0.89348(15) 0.0624(6) Uani 1 1 d . . . . .
H32 H 0.6622 1.1738 0.9188 0.075 Uiso 1 1 calc R U . . .
C19 C 0.1978(3) 0.3734(2) 0.43187(17) 0.0650(6) Uani 1 1 d . . . . .
H19 H 0.2159 0.2933 0.4119 0.078 Uiso 1 1 calc R U . . .
C23 C 0.0278(2) 0.7942(2) 0.49171(18) 0.0674(7) Uani 1 1 d . . . . .
H23A H -0.0309 0.7983 0.5249 0.101 Uiso 1 1 calc R U . . .
H23B H -0.0162 0.7499 0.4323 0.101 Uiso 1 1 calc R U . . .
H23C H 0.0579 0.8750 0.4980 0.101 Uiso 1 1 calc R U . . .
C4 C 0.3344(2) 0.5444(2) 0.92647(15) 0.0632(6) Uani 1 1 d . . . . .
H4A H 0.3944 0.4868 0.9363 0.095 Uiso 1 1 calc R U . . .
H4B H 0.2631 0.5350 0.9475 0.095 Uiso 1 1 calc R U . . .
H4C H 0.3778 0.6254 0.9560 0.095 Uiso 1 1 calc R U . . .
C30 C 0.8208(2) 0.9336(3) 0.89064(17) 0.0682(7) Uani 1 1 d . . . . .
H30 H 0.8991 0.9091 0.9157 0.082 Uiso 1 1 calc R U . . .
C37 C 0.3648(3) 1.1354(2) 0.49404(19) 0.0709(7) Uani 1 1 d . . . . .
H37 H 0.3838 1.1824 0.4638 0.085 Uiso 1 1 calc R U . . .
C6 C 0.1874(2) 0.6173(3) 0.82001(18) 0.0678(7) Uani 1 1 d . . . . .
H6A H 0.2321 0.6975 0.8513 0.102 Uiso 1 1 calc R U . . .
H6B H 0.1182 0.6060 0.8424 0.102 Uiso 1 1 calc R U . . .
H6C H 0.1522 0.6078 0.7604 0.102 Uiso 1 1 calc R U . . .
C31 C 0.7920(3) 1.0514(3) 0.92553(17) 0.0690(7) Uani 1 1 d . . . . .
C5 C 0.2050(2) 0.3959(2) 0.78116(17) 0.0666(6) Uani 1 1 d . . . . .
H5A H 0.1720 0.3844 0.7211 0.100 Uiso 1 1 calc R U . . .
H5B H 0.1338 0.3904 0.8033 0.100 Uiso 1 1 calc R U . . .
H5C H 0.2604 0.3342 0.7889 0.100 Uiso 1 1 calc R U . . .
C38 C 0.3600(3) 1.1894(2) 0.57627(19) 0.0707(7) Uani 1 1 d . . . . .
H38 H 0.3743 1.2736 0.6016 0.085 Uiso 1 1 calc R U . . .
C36 C 0.3411(3) 1.0110(2) 0.45652(17) 0.0674(7) Uani 1 1 d . . . . .
H36 H 0.3429 0.9739 0.4003 0.081 Uiso 1 1 calc R U . . .
C45 C 0.0582(3) 0.9237(3) 0.7727(2) 0.0770(8) Uani 1 1 d . . . . .
H45 H 0.0464 0.8849 0.8096 0.092 Uiso 1 1 calc R U . . .
C14 C 0.8093(3) 0.4282(3) 0.7229(2) 0.0890(10) Uani 1 1 d . . . . .
H14A H 0.7618 0.4040 0.6630 0.133 Uiso 1 1 calc R U . . .
H14B H 0.8821 0.3820 0.7303 0.133 Uiso 1 1 calc R U . . .
H14C H 0.8398 0.5132 0.7443 0.133 Uiso 1 1 calc R U . . .
C42 C 0.0965(3) 1.0385(3) 0.66454(18) 0.0702(7) Uani 1 1 d . . . . .
H42 H 0.1086 1.0788 0.6285 0.084 Uiso 1 1 calc R U . . .
C13 C 0.6814(3) 0.2672(2) 0.7376(2) 0.0825(9) Uani 1 1 d . . . . .
H13A H 0.6271 0.2467 0.7676 0.124 Uiso 1 1 calc R U . . .
H13B H 0.7582 0.2261 0.7454 0.124 Uiso 1 1 calc R U . . .
H13C H 0.6349 0.2425 0.6775 0.124 Uiso 1 1 calc R U . . .
C44 C -0.0256(3) 1.0041(3) 0.7525(2) 0.0875(9) Uani 1 1 d . . . . .
H44 H -0.0953 1.0190 0.7748 0.105 Uiso 1 1 calc R U . . .
C43 C -0.0061(3) 1.0623(3) 0.6995(2) 0.0880(9) Uani 1 1 d . . . . .
H43 H -0.0618 1.1182 0.6866 0.106 Uiso 1 1 calc R U . . .
C12 C 0.7981(3) 0.4445(3) 0.8671(2) 0.0938(10) Uani 1 1 d . . . . .
H12A H 0.8225 0.5307 0.8886 0.141 Uiso 1 1 calc R U . . .
H12B H 0.8748 0.4032 0.8732 0.141 Uiso 1 1 calc R U . . .
H12C H 0.7467 0.4248 0.8991 0.141 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 0.0033 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'
F F 0.0171 0.0103 '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
C24 N1 C23 129.46(18) . . ?
C22 N1 C24 107.85(16) . . ?
C22 N1 C23 122.56(18) . . ?
C26 N2 H2 125.6 . . ?
C33 N2 H2 125.6 . . ?
C33 N2 C26 108.87(18) . . ?
C24 C16 C15 125.69(18) . . ?
C24 C16 C17 107.16(18) . . ?
C17 C16 C15 127.11(17) . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.45(18) . . ?
C10 C9 H9 118.8 . . ?
N2 C26 C25 121.82(17) . . ?
C27 C26 N2 109.29(18) . . ?
C27 C26 C25 128.79(19) . . ?
N1 C24 C25 123.26(16) . . ?
C16 C24 N1 109.64(18) . . ?
C16 C24 C25 127.10(18) . . ?
C33 C28 C27 106.18(18) . . ?
C29 C28 C27 135.3(2) . . ?
C29 C28 C33 118.5(2) . . ?
C9 C8 C15 120.80(17) . . ?
C7 C8 C9 118.22(17) . . ?
C7 C8 C15 120.94(17) . . ?
C16 C15 C8 111.92(16) . . ?
C16 C15 H15 108.4 . . ?
C8 C15 H15 108.4 . . ?
C27 C15 C16 108.43(16) . . ?
C27 C15 C8 111.26(16) . . ?
C27 C15 H15 108.4 . . ?
C26 C27 C28 107.32(18) . . ?
C26 C27 C15 124.22(18) . . ?
C28 C27 C15 128.34(17) . . ?
C8 C7 H7 118.4 . . ?
C8 C7 C2 123.11(18) . . ?
C2 C7 H7 118.4 . . ?
C7 C2 C1 116.94(17) . . ?
C7 C2 C3 120.64(17) . . ?
C1 C2 C3 122.39(17) . . ?
C9 C10 C1 117.19(17) . . ?
C9 C10 C11 121.07(17) . . ?
C1 C10 C11 121.73(17) . . ?
C22 C17 C16 106.82(17) . . ?
C18 C17 C16 134.1(2) . . ?
C18 C17 C22 119.0(2) . . ?
C26 C25 C24 105.00(15) . . ?
C26 C25 C40 107.68(16) . . ?
C26 C25 C41 110.61(16) . . ?
C24 C25 C40 111.10(16) . . ?
C24 C25 C41 108.94(16) . . ?
C40 C25 C41 113.20(15) . . ?
C35 C40 C25 121.85(18) . . ?
C35 C40 C39 117.25(19) . . ?
C39 C40 C25 120.73(19) . . ?
O1 C1 C2 122.51(17) . . ?
O1 C1 C10 115.42(17) . . ?
C2 C1 C10 122.07(17) . . ?
N1 C22 C17 108.52(18) . . ?
N1 C22 C21 129.3(2) . . ?
C21 C22 C17 122.2(2) . . ?
C4 C3 C2 112.86(18) . . ?
C4 C3 C6 105.83(19) . . ?
C4 C3 C5 110.61(19) . . ?
C6 C3 C2 111.05(17) . . ?
C5 C3 C2 109.24(18) . . ?
C5 C3 C6 107.1(2) . . ?
C46 C41 C25 118.13(18) . . ?
C42 C41 C25 123.95(19) . . ?
C42 C41 C46 117.8(2) . . ?
C10 C11 C14 110.95(18) . . ?
C13 C11 C10 111.44(19) . . ?
C13 C11 C14 105.6(2) . . ?
C12 C11 C10 110.8(2) . . ?
C12 C11 C14 107.8(2) . . ?
C12 C11 C13 110.1(2) . . ?
N2 C33 C28 108.33(19) . . ?
N2 C33 C32 128.8(2) . . ?
C32 C33 C28 122.9(2) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 C22 117.3(2) . . ?
C20 C21 H21 121.3 . . ?
C40 C35 H35 119.5 . . ?
C40 C35 C36 121.1(2) . . ?
C36 C35 H35 119.5 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.3(2) . . ?
C30 C29 H29 120.3 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.3(2) . . ?
C19 C18 H18 120.8 . . ?
C41 C46 H46 119.4 . . ?
C41 C46 C45 121.2(2) . . ?
C45 C46 H46 119.4 . . ?
C21 C20 H20 119.2 . . ?
C21 C20 C19 121.6(2) . . ?
C19 C20 H20 119.2 . . ?
C40 C39 H39 119.3 . . ?
C38 C39 C40 121.3(2) . . ?
C38 C39 H39 119.3 . . ?
C33 C32 H32 122.2 . . ?
C31 C32 C33 115.7(2) . . ?
C31 C32 H32 122.2 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.4(2) . . ?
C31 C30 H30 120.3 . . ?
C38 C37 H37 120.3 . . ?
C38 C37 C36 119.3(2) . . ?
C36 C37 H37 120.3 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F1 C31 C30 117.4(2) . . ?
C32 C31 F1 118.4(3) . . ?
C32 C31 C30 124.2(2) . . ?
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 . . ?
C39 C38 H38 119.8 . . ?
C37 C38 C39 120.5(2) . . ?
C37 C38 H38 119.8 . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.5(2) . . ?
C37 C36 H36 119.7 . . ?
C46 C45 H45 120.0 . . ?
C44 C45 C46 120.0(3) . . ?
C44 C45 H45 120.0 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C41 C42 H42 119.5 . . ?
C41 C42 C43 121.0(3) . . ?
C43 C42 H42 119.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C45 C44 H44 120.2 . . ?
C43 C44 C45 119.5(3) . . ?
C43 C44 H44 120.2 . . ?
C42 C43 H43 119.8 . . ?
C44 C43 C42 120.5(3) . . ?
C44 C43 H43 119.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 C24 1.399(3) . ?
N1 C22 1.385(3) . ?
N1 C23 1.448(3) . ?
O1 C1 1.376(2) . ?
F1 C31 1.367(3) . ?
N2 H2 0.8600 . ?
N2 C26 1.383(3) . ?
N2 C33 1.376(3) . ?
C16 C24 1.373(3) . ?
C16 C15 1.507(3) . ?
C16 C17 1.437(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.389(3) . ?
C9 C10 1.395(3) . ?
C26 C27 1.370(3) . ?
C26 C25 1.512(3) . ?
C24 C25 1.520(3) . ?
C28 C27 1.443(3) . ?
C28 C33 1.409(3) . ?
C28 C29 1.401(3) . ?
C8 C15 1.534(2) . ?
C8 C7 1.386(3) . ?
C15 H15 0.9800 . ?
C15 C27 1.507(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.389(3) . ?
C2 C1 1.412(3) . ?
C2 C3 1.554(3) . ?
C10 C1 1.415(3) . ?
C10 C11 1.543(3) . ?
C17 C22 1.409(3) . ?
C17 C18 1.397(3) . ?
C25 C40 1.550(3) . ?
C25 C41 1.553(3) . ?
C40 C35 1.390(3) . ?
C40 C39 1.394(3) . ?
C22 C21 1.389(3) . ?
C3 C4 1.537(3) . ?
C3 C6 1.543(3) . ?
C3 C5 1.542(3) . ?
C41 C46 1.385(3) . ?
C41 C42 1.378(3) . ?
C11 C14 1.545(3) . ?
C11 C13 1.533(4) . ?
C11 C12 1.515(4) . ?
C33 C32 1.396(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.375(3) . ?
C35 H35 0.9300 . ?
C35 C36 1.394(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(3) . ?
C46 H46 0.9300 . ?
C46 C45 1.392(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(4) . ?
C39 H39 0.9300 . ?
C39 C38 1.392(3) . ?
C32 H32 0.9300 . ?
C32 C31 1.363(4) . ?
C19 H19 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C30 H30 0.9300 . ?
C30 C31 1.389(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.368(4) . ?
C37 C36 1.375(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C38 H38 0.9300 . ?
C36 H36 0.9300 . ?
C45 H45 0.9300 . ?
C45 C44 1.370(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C42 H42 0.9300 . ?
C42 C43 1.393(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C44 H44 0.9300 . ?
C44 C43 1.365(5) . ?
C43 H43 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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 C24 C25 C26 171.76(17) . . . . ?
N1 C24 C25 C40 -72.1(2) . . . . ?
N1 C24 C25 C41 53.3(2) . . . . ?
N1 C22 C21 C20 179.7(2) . . . . ?
N2 C26 C27 C28 -1.0(2) . . . . ?
N2 C26 C27 C15 175.23(17) . . . . ?
N2 C26 C25 C24 -173.50(17) . . . . ?
N2 C26 C25 C40 68.0(2) . . . . ?
N2 C26 C25 C41 -56.1(2) . . . . ?
N2 C33 C32 C31 -178.9(2) . . . . ?
C16 C24 C25 C26 -7.6(3) . . . . ?
C16 C24 C25 C40 108.5(2) . . . . ?
C16 C24 C25 C41 -126.1(2) . . . . ?
C16 C15 C27 C26 1.3(2) . . . . ?
C16 C15 C27 C28 176.71(18) . . . . ?
C16 C17 C22 N1 0.8(2) . . . . ?
C16 C17 C22 C21 -177.92(18) . . . . ?
C16 C17 C18 C19 179.7(2) . . . . ?
C9 C8 C15 C16 133.7(2) . . . . ?
C9 C8 C15 C27 -104.8(2) . . . . ?
C9 C8 C7 C2 -0.5(3) . . . . ?
C9 C10 C1 O1 179.08(19) . . . . ?
C9 C10 C1 C2 -1.1(3) . . . . ?
C9 C10 C11 C14 -2.8(3) . . . . ?
C9 C10 C11 C13 -120.1(2) . . . . ?
C9 C10 C11 C12 116.9(3) . . . . ?
C26 N2 C33 C28 0.3(2) . . . . ?
C26 N2 C33 C32 -179.6(2) . . . . ?
C26 C25 C40 C35 106.6(2) . . . . ?
C26 C25 C40 C39 -68.5(2) . . . . ?
C26 C25 C41 C46 -53.5(2) . . . . ?
C26 C25 C41 C42 131.1(2) . . . . ?
C24 N1 C22 C17 -0.3(2) . . . . ?
C24 N1 C22 C21 178.4(2) . . . . ?
C24 C16 C15 C8 124.5(2) . . . . ?
C24 C16 C15 C27 1.4(2) . . . . ?
C24 C16 C17 C22 -1.1(2) . . . . ?
C24 C16 C17 C18 179.0(2) . . . . ?
C24 C25 C40 C35 -7.9(3) . . . . ?
C24 C25 C40 C39 177.04(19) . . . . ?
C24 C25 C41 C46 61.4(2) . . . . ?
C24 C25 C41 C42 -114.0(2) . . . . ?
C28 C33 C32 C31 1.3(3) . . . . ?
C28 C29 C30 C31 -0.9(3) . . . . ?
C8 C9 C10 C1 0.6(3) . . . . ?
C8 C9 C10 C11 -178.16(19) . . . . ?
C8 C15 C27 C26 -122.2(2) . . . . ?
C8 C15 C27 C28 53.2(2) . . . . ?
C8 C7 C2 C1 0.0(3) . . . . ?
C8 C7 C2 C3 -177.92(19) . . . . ?
C15 C16 C24 N1 -176.93(17) . . . . ?
C15 C16 C24 C25 2.5(3) . . . . ?
C15 C16 C17 C22 176.76(17) . . . . ?
C15 C16 C17 C18 -3.2(3) . . . . ?
C15 C8 C7 C2 -178.35(19) . . . . ?
C27 C26 C25 C24 10.7(3) . . . . ?
C27 C26 C25 C40 -107.8(2) . . . . ?
C27 C26 C25 C41 128.1(2) . . . . ?
C27 C28 C33 N2 -0.9(2) . . . . ?
C27 C28 C33 C32 179.0(2) . . . . ?
C27 C28 C29 C30 -179.5(2) . . . . ?
C7 C8 C15 C16 -48.5(2) . . . . ?
C7 C8 C15 C27 73.0(2) . . . . ?
C7 C2 C1 O1 -179.42(19) . . . . ?
C7 C2 C1 C10 0.8(3) . . . . ?
C7 C2 C3 C4 -128.0(2) . . . . ?
C7 C2 C3 C6 -9.3(3) . . . . ?
C7 C2 C3 C5 108.5(2) . . . . ?
C10 C9 C8 C15 177.99(18) . . . . ?
C10 C9 C8 C7 0.1(3) . . . . ?
C17 C16 C24 N1 1.0(2) . . . . ?
C17 C16 C24 C25 -179.62(17) . . . . ?
C17 C16 C15 C8 -52.9(2) . . . . ?
C17 C16 C15 C27 -176.05(17) . . . . ?
C17 C22 C21 C20 -1.8(3) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
C25 C26 C27 C28 175.23(18) . . . . ?
C25 C26 C27 C15 -8.5(3) . . . . ?
C25 C40 C35 C36 -176.1(2) . . . . ?
C25 C40 C39 C38 176.4(2) . . . . ?
C25 C41 C46 C45 -173.9(2) . . . . ?
C25 C41 C42 C43 173.9(3) . . . . ?
C40 C25 C41 C46 -174.48(19) . . . . ?
C40 C25 C41 C42 10.1(3) . . . . ?
C40 C35 C36 C37 0.8(4) . . . . ?
C40 C39 C38 C37 -1.2(4) . . . . ?
C1 C2 C3 C4 54.2(3) . . . . ?
C1 C2 C3 C6 172.8(2) . . . . ?
C1 C2 C3 C5 -69.3(3) . . . . ?
C1 C10 C11 C14 178.5(2) . . . . ?
C1 C10 C11 C13 61.1(3) . . . . ?
C1 C10 C11 C12 -61.8(3) . . . . ?
C22 N1 C24 C16 -0.5(2) . . . . ?
C22 N1 C24 C25 -179.90(16) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C22 C21 C20 C19 -0.2(4) . . . . ?
C3 C2 C1 O1 -1.5(3) . . . . ?
C3 C2 C1 C10 178.71(19) . . . . ?
C41 C25 C40 C35 -130.8(2) . . . . ?
C41 C25 C40 C39 54.1(3) . . . . ?
C41 C46 C45 C44 -0.4(4) . . . . ?
C41 C42 C43 C44 0.0(5) . . . . ?
C11 C10 C1 O1 -2.1(3) . . . . ?
C11 C10 C1 C2 177.7(2) . . . . ?
C33 N2 C26 C27 0.5(2) . . . . ?
C33 N2 C26 C25 -176.07(18) . . . . ?
C33 C28 C27 C26 1.1(2) . . . . ?
C33 C28 C27 C15 -174.88(18) . . . . ?
C33 C28 C29 C30 1.3(3) . . . . ?
C33 C32 C31 F1 179.2(2) . . . . ?
C33 C32 C31 C30 -0.8(4) . . . . ?
C21 C20 C19 C18 2.0(4) . . . . ?
C35 C40 C39 C38 1.1(4) . . . . ?
C29 C28 C27 C26 -178.2(2) . . . . ?
C29 C28 C27 C15 5.8(4) . . . . ?
C29 C28 C33 N2 178.57(19) . . . . ?
C29 C28 C33 C32 -1.5(3) . . . . ?
C29 C30 C31 F1 -179.4(2) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C18 C17 C22 N1 -179.22(17) . . . . ?
C18 C17 C22 C21 2.0(3) . . . . ?
C46 C41 C42 C43 -1.5(4) . . . . ?
C46 C45 C44 C43 -1.1(5) . . . . ?
C39 C40 C35 C36 -0.9(3) . . . . ?
C23 N1 C24 C16 -176.3(2) . . . . ?
C23 N1 C24 C25 4.3(3) . . . . ?
C23 N1 C22 C17 175.9(2) . . . . ?
C23 N1 C22 C21 -5.5(3) . . . . ?
C38 C37 C36 C35 -1.0(4) . . . . ?
C36 C37 C38 C39 1.2(4) . . . . ?
C45 C44 C43 C42 1.3(5) . . . . ?
C42 C41 C46 C45 1.8(4) . . . . ?
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 0.345 0.155 1.000 380.0 70.9 ?
2 0.423 0.666 0.439 9.9 0.0 ?
3 0.577 0.334 0.561 9.9 0.0 ?
