#------------------------------------------------------------------------------
#$Date: 2024-04-05 03:07:25 +0300 (Fri, 05 Apr 2024) $
#$Revision: 291035 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/30/7063042.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_7063042
loop_
_publ_author_name
'Zhang, Wen-Hui'
'Zhang, Bo'
'Pan, Bo-Wen'
'Liu, Xiong-Wei'
'Yin, Zhi-Gang'
'Zhuo, Yu-Zhou'
'Lei, Chuan-wen'
'Zhou, Ying'
_publ_section_title
;
 Design, synthesis, and evaluation of 1,4-naphthoquinone-chromene hybrids
 as potential anti-K562 and A549 agents
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5334
_journal_page_last               5345
_journal_paper_doi               10.1039/D3NJ05743G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C24 H17 F N2 O6'
_chemical_formula_sum            'C24 H17 F N2 O6'
_chemical_formula_weight         448.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-19
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-11-17 deposited with the CCDC.	2024-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                92.135(5)
_cell_angle_beta                 101.797(6)
_cell_angle_gamma                108.263(7)
_cell_formula_units_Z            2
_cell_length_a                   8.7150(8)
_cell_length_b                   10.4907(8)
_cell_length_c                   12.3492(6)
_cell_measurement_reflns_used    4907
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.7090
_cell_measurement_theta_min      3.6530
_cell_volume                     1043.27(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  33.00   1.00    1.00    --  -40.92  37.00 -30.00   97
  2  ω     89.00 115.00   1.00    1.00    --   40.92  37.00-150.00   26
  3  ω     79.00 144.00   1.00    1.00    --  107.58 -15.00 -90.00   65
  4  ω    147.00 178.00   1.00    1.00    --  107.58  61.00   0.00   31
  5  ω    152.00 178.00   1.00    1.00    --  107.58 125.00  60.00   26
  6  ω    104.00 162.00   1.00    1.00    --  107.58 125.00  30.00   58
  7  ω     97.00 176.00   1.00    1.00    --  107.58  45.00  90.00   79
  8  ω    106.00 132.00   1.00    1.00    --  107.58 -61.00 120.00   26
  9  ω     76.00 103.00   1.00    1.00    --  107.58 -94.00  90.00   27
 10  ω     45.00  74.00   1.00    1.00    --  107.58 -61.00 120.00   29
 11  ω     43.00 136.00   1.00    1.00    --  107.58 -30.00  60.00   93
 12  ω     80.00 119.00   1.00    1.00    --  107.58  61.00   0.00   39
 13  ω     32.00  60.00   1.00    1.00    --  107.58 -15.00 -90.00   28
 14  ω     36.00 121.00   1.00    1.00    --  107.58 -61.00   0.00   85
 15  ω     55.00 121.00   1.00    1.00    --  107.58-125.00-120.00   66
 16  ω     35.00  82.00   1.00    1.00    --   40.92 -99.00  30.00   47
 17  ω     35.00 108.00   1.00    1.00    --  107.58 -94.00 -30.00   73
 18  ω      2.00  36.00   1.00    1.00    --   40.92 -99.00  60.00   34
 19  ω   -106.00 -17.00   1.00    1.00    --  -40.92 -37.00 150.00   89
 20  ω    -54.00 -17.00   1.00    1.00    --  -40.92 125.00  60.00   37
 21  ω    -96.00 -56.00   1.00    1.00    --  -40.92 125.00  60.00   40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0974561000
_diffrn_orient_matrix_UB_12      -0.0867599000
_diffrn_orient_matrix_UB_13      -0.1109322000
_diffrn_orient_matrix_UB_21      -0.0847910000
_diffrn_orient_matrix_UB_22      -0.1145229000
_diffrn_orient_matrix_UB_23      0.0642509000
_diffrn_orient_matrix_UB_31      -0.1409228000
_diffrn_orient_matrix_UB_32      0.0596532000
_diffrn_orient_matrix_UB_33      -0.0015496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6860
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.837
_diffrn_reflns_theta_min         3.678
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         4079
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0400
_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)+(0.0645P)²+0.2765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3769
_reflns_number_total             4079
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj05743g2.cif
_cod_data_source_block           yes-21
_cod_depositor_comments          'Adding full bibliography for 7063042.cif.'
_cod_database_code               7063042
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 N2(H2A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2023-05-18
_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.429
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
F1 F 0.40692(12) 0.37690(9) 0.63247(7) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.73675(12) 0.64138(10) 0.11397(9) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.14025(11) 0.35812(10) 0.17284(9) 0.0335(2) Uani 1 1 d . . . . .
O3 O 0.70244(10) 0.40938(9) 0.18912(8) 0.0254(2) Uani 1 1 d . . . . .
O4 O 0.23290(11) 0.08252(9) 0.07167(7) 0.0258(2) Uani 1 1 d . . . . .
O5 O 0.68094(12) 0.04034(11) 0.31159(9) 0.0345(2) Uani 1 1 d . . . . .
O6 O 0.41528(11) 0.00259(9) 0.31730(8) 0.0260(2) Uani 1 1 d . . . . .
N1 N 0.12402(12) 0.08186(10) 0.22634(8) 0.0204(2) Uani 1 1 d . . . . .
N2 N 0.83887(15) 0.26929(14) 0.24212(12) 0.0371(3) Uani 1 1 d . . . . .
H2A H 0.831319 0.192628 0.262822 0.056 Uiso 1 1 calc R U . . .
H2B H 0.919(2) 0.326(2) 0.2149(16) 0.046(5) Uiso 1 1 d . . . . .
C1 C 0.46074(16) 0.63754(13) 0.10610(10) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.48542(18) 0.76462(14) 0.06874(11) 0.0288(3) Uani 1 1 d . . . . .
H2 H 0.590888 0.815732 0.057262 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3548(2) 0.81591(14) 0.04844(12) 0.0333(3) Uani 1 1 d . . . . .
H3 H 0.371373 0.902677 0.023346 0.040 Uiso 1 1 calc R U . . .
C4 C 0.19977(19) 0.74120(15) 0.06456(12) 0.0328(3) Uani 1 1 d . . . . .
H4 H 0.111024 0.777077 0.050352 0.039 Uiso 1 1 calc R U . . .
C5 C 0.17455(17) 0.61432(14) 0.10137(11) 0.0284(3) Uani 1 1 d . . . . .
H5 H 0.068598 0.563353 0.112181 0.034 Uiso 1 1 calc R U . . .
C6 C 0.30476(16) 0.56196(13) 0.12241(10) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.27729(15) 0.42608(13) 0.16181(10) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.41709(14) 0.37271(12) 0.18850(9) 0.0191(2) Uani 1 1 d . . . . .
C9 C 0.59941(16) 0.58248(13) 0.12798(10) 0.0232(3) Uani 1 1 d . . . . .
C10 C 0.56398(15) 0.44630(13) 0.16986(10) 0.0207(3) Uani 1 1 d . . . . .
C11 C 0.39275(14) 0.24026(12) 0.23984(10) 0.0186(2) Uani 1 1 d . . . . .
C12 C 0.55106(15) 0.20368(13) 0.25342(10) 0.0214(3) Uani 1 1 d . . . . .
C13 C 0.69212(16) 0.28781(14) 0.22928(11) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.55913(15) 0.07765(13) 0.29560(11) 0.0239(3) Uani 1 1 d . . . . .
C15 C 0.41690(18) -0.12196(14) 0.36426(13) 0.0307(3) Uani 1 1 d . . . . .
H15A H 0.506721 -0.102902 0.432350 0.037 Uiso 1 1 calc R U . . .
H15B H 0.435710 -0.184048 0.309957 0.037 Uiso 1 1 calc R U . . .
C16 C 0.2508(2) -0.18445(17) 0.39156(16) 0.0439(4) Uani 1 1 d . . . . .
H16A H 0.163268 -0.204401 0.323312 0.066 Uiso 1 1 calc R U . . .
H16B H 0.232948 -0.121418 0.444341 0.066 Uiso 1 1 calc R U . . .
H16C H 0.248036 -0.268275 0.424847 0.066 Uiso 1 1 calc R U . . .
C17 C 0.24162(14) 0.12607(12) 0.16601(10) 0.0196(2) Uani 1 1 d . . . . .
C18 C 0.33394(14) 0.24525(12) 0.34723(10) 0.0186(2) Uani 1 1 d . . . . .
C19 C 0.41442(15) 0.32269(12) 0.44694(10) 0.0221(3) Uani 1 1 d . . . . .
H19 H 0.522306 0.387003 0.457216 0.027 Uiso 1 1 calc R U . . .
C20 C 0.32966(17) 0.30202(13) 0.53214(11) 0.0262(3) Uani 1 1 d . . . . .
C21 C 0.17415(18) 0.21009(14) 0.52073(11) 0.0279(3) Uani 1 1 d . . . . .
H21 H 0.121408 0.200357 0.581507 0.034 Uiso 1 1 calc R U . . .
C22 C 0.09385(15) 0.13101(13) 0.41953(11) 0.0236(3) Uani 1 1 d . . . . .
H22 H -0.013711 0.066365 0.409798 0.028 Uiso 1 1 calc R U . . .
C23 C 0.17611(14) 0.14984(12) 0.33368(10) 0.0194(2) Uani 1 1 d . . . . .
C24 C -0.02947(15) -0.02909(14) 0.18459(11) 0.0272(3) Uani 1 1 d . . . . .
H24A H -0.047855 -0.047056 0.103714 0.041 Uiso 1 1 calc R U . . .
H24B H -0.122138 -0.005092 0.202452 0.041 Uiso 1 1 calc R U . . .
H24C H -0.022024 -0.110014 0.219434 0.041 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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O3 C13 118.08(10) . . ?
C14 O6 C15 115.39(10) . . ?
C17 N1 C23 111.49(10) . . ?
C17 N1 C24 122.97(10) . . ?
C23 N1 C24 125.38(10) . . ?
H2A N2 H2B 129.3 . . ?
C13 N2 H2A 109.5 . . ?
C13 N2 H2B 119.6(12) . . ?
C2 C1 C6 120.16(12) . . ?
C2 C1 C9 119.75(12) . . ?
C6 C1 C9 120.09(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.52(13) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.51(13) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.13(13) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.89(13) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 120.47(11) . . ?
C5 C6 C1 119.79(12) . . ?
C5 C6 C7 119.74(12) . . ?
O2 C7 C6 120.68(12) . . ?
O2 C7 C8 119.53(11) . . ?
C8 C7 C6 119.79(11) . . ?
C7 C8 C11 119.55(10) . . ?
C10 C8 C7 118.23(11) . . ?
C10 C8 C11 122.18(11) . . ?
O1 C9 C1 123.59(12) . . ?
O1 C9 C10 119.81(12) . . ?
C1 C9 C10 116.60(11) . . ?
O3 C10 C9 110.53(10) . . ?
C8 C10 O3 124.73(11) . . ?
C8 C10 C9 124.72(11) . . ?
C8 C11 C12 109.36(10) . . ?
C8 C11 C17 110.32(9) . . ?
C8 C11 C18 111.51(10) . . ?
C12 C11 C17 111.03(10) . . ?
C18 C11 C12 113.58(10) . . ?
C18 C11 C17 100.80(9) . . ?
C13 C12 C11 122.07(11) . . ?
C13 C12 C14 117.03(11) . . ?
C14 C12 C11 120.88(10) . . ?
N2 C13 O3 109.26(11) . . ?
N2 C13 C12 127.38(13) . . ?
C12 C13 O3 123.34(11) . . ?
O5 C14 O6 121.55(12) . . ?
O5 C14 C12 125.89(12) . . ?
O6 C14 C12 112.55(10) . . ?
O6 C15 H15A 110.3 . . ?
O6 C15 H15B 110.3 . . ?
O6 C15 C16 107.14(11) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 N1 126.11(11) . . ?
O4 C17 C11 125.34(10) . . ?
N1 C17 C11 108.53(10) . . ?
C19 C18 C11 129.62(11) . . ?
C19 C18 C23 121.17(11) . . ?
C23 C18 C11 109.16(10) . . ?
C18 C19 H19 121.8 . . ?
C18 C19 C20 116.45(12) . . ?
C20 C19 H19 121.8 . . ?
F1 C20 C19 117.81(12) . . ?
F1 C20 C21 118.65(12) . . ?
C21 C20 C19 123.54(12) . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.66(12) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 121.1 . . ?
C23 C22 C21 117.73(12) . . ?
C23 C22 H22 121.1 . . ?
C18 C23 N1 110.01(10) . . ?
C22 C23 N1 128.55(11) . . ?
C22 C23 C18 121.43(11) . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
F1 C20 1.3639(15) . ?
O1 C9 1.2139(16) . ?
O2 C7 1.2220(15) . ?
O3 C10 1.3583(15) . ?
O3 C13 1.3689(16) . ?
O4 C17 1.2142(15) . ?
O5 C14 1.2246(16) . ?
O6 C14 1.3408(15) . ?
O6 C15 1.4521(15) . ?
N1 C17 1.3640(15) . ?
N1 C23 1.3973(15) . ?
N1 C24 1.4516(15) . ?
N2 H2A 0.8400 . ?
N2 H2B 0.90(2) . ?
N2 C13 1.3317(17) . ?
C1 C2 1.3939(18) . ?
C1 C6 1.4019(18) . ?
C1 C9 1.4774(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3921(19) . ?
C6 C7 1.4871(17) . ?
C7 C8 1.4777(17) . ?
C8 C10 1.3424(17) . ?
C8 C11 1.5210(16) . ?
C9 C10 1.4993(17) . ?
C11 C12 1.5235(16) . ?
C11 C17 1.5620(16) . ?
C11 C18 1.5211(16) . ?
C12 C13 1.3669(17) . ?
C12 C14 1.4556(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.503(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C18 C19 1.3724(17) . ?
C18 C23 1.3972(16) . ?
C19 H19 0.9500 . ?
C19 C20 1.3908(18) . ?
C20 C21 1.371(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.3932(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3837(17) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
F1 C20 C21 C22 -179.02(12) . . . . ?
O1 C9 C10 O3 1.44(17) . . . . ?
O1 C9 C10 C8 179.83(12) . . . . ?
O2 C7 C8 C10 176.44(12) . . . . ?
O2 C7 C8 C11 -5.88(18) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C6 C7 O2 -177.73(12) . . . . ?
C1 C6 C7 C8 2.59(18) . . . . ?
C1 C9 C10 O3 -178.46(10) . . . . ?
C1 C9 C10 C8 -0.07(18) . . . . ?
C2 C1 C6 C5 -0.13(19) . . . . ?
C2 C1 C6 C7 179.75(11) . . . . ?
C2 C1 C9 O1 -0.9(2) . . . . ?
C2 C1 C9 C10 178.96(11) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C7 180.00(12) . . . . ?
C5 C6 C7 O2 2.15(19) . . . . ?
C5 C6 C7 C8 -177.53(11) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
C6 C1 C9 O1 178.79(12) . . . . ?
C6 C1 C9 C10 -1.32(17) . . . . ?
C6 C7 C8 C10 -3.87(17) . . . . ?
C6 C7 C8 C11 173.81(10) . . . . ?
C7 C8 C10 O3 -179.20(11) . . . . ?
C7 C8 C10 C9 2.64(18) . . . . ?
C7 C8 C11 C12 176.95(10) . . . . ?
C7 C8 C11 C17 54.56(14) . . . . ?
C7 C8 C11 C18 -56.59(14) . . . . ?
C8 C11 C12 C13 4.61(16) . . . . ?
C8 C11 C12 C14 -176.86(10) . . . . ?
C8 C11 C17 O4 64.31(15) . . . . ?
C8 C11 C17 N1 -117.18(10) . . . . ?
C8 C11 C18 C19 -65.57(16) . . . . ?
C8 C11 C18 C23 116.77(11) . . . . ?
C9 C1 C2 C3 -179.93(12) . . . . ?
C9 C1 C6 C5 -179.85(11) . . . . ?
C9 C1 C6 C7 0.03(18) . . . . ?
C10 O3 C13 N2 179.66(11) . . . . ?
C10 O3 C13 C12 -1.66(18) . . . . ?
C10 C8 C11 C12 -5.46(16) . . . . ?
C10 C8 C11 C17 -127.86(12) . . . . ?
C10 C8 C11 C18 121.00(12) . . . . ?
C11 C8 C10 O3 3.18(19) . . . . ?
C11 C8 C10 C9 -174.97(10) . . . . ?
C11 C12 C13 O3 -1.4(2) . . . . ?
C11 C12 C13 N2 177.03(13) . . . . ?
C11 C12 C14 O5 -178.45(12) . . . . ?
C11 C12 C14 O6 1.07(17) . . . . ?
C11 C18 C19 C20 -178.23(12) . . . . ?
C11 C18 C23 N1 -0.24(13) . . . . ?
C11 C18 C23 C22 178.83(11) . . . . ?
C12 C11 C17 O4 -57.10(16) . . . . ?
C12 C11 C17 N1 121.41(11) . . . . ?
C12 C11 C18 C19 58.55(17) . . . . ?
C12 C11 C18 C23 -119.11(11) . . . . ?
C13 O3 C10 C8 0.77(18) . . . . ?
C13 O3 C10 C9 179.15(10) . . . . ?
C13 C12 C14 O5 0.1(2) . . . . ?
C13 C12 C14 O6 179.67(11) . . . . ?
C14 O6 C15 C16 175.15(12) . . . . ?
C14 C12 C13 O3 -179.98(11) . . . . ?
C14 C12 C13 N2 -1.6(2) . . . . ?
C15 O6 C14 O5 2.12(18) . . . . ?
C15 O6 C14 C12 -177.43(11) . . . . ?
C17 N1 C23 C18 0.79(14) . . . . ?
C17 N1 C23 C22 -178.20(12) . . . . ?
C17 C11 C12 C13 126.58(12) . . . . ?
C17 C11 C12 C14 -54.89(15) . . . . ?
C17 C11 C18 C19 177.36(12) . . . . ?
C17 C11 C18 C23 -0.31(12) . . . . ?
C18 C11 C12 C13 -120.66(13) . . . . ?
C18 C11 C12 C14 57.86(15) . . . . ?
C18 C11 C17 O4 -177.74(12) . . . . ?
C18 C11 C17 N1 0.77(12) . . . . ?
C18 C19 C20 F1 179.58(11) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C18 C23 N1 -178.14(11) . . . . ?
C19 C18 C23 C22 0.93(18) . . . . ?
C19 C20 C21 C22 0.4(2) . . . . ?
C20 C21 C22 C23 -0.30(19) . . . . ?
C21 C22 C23 N1 178.53(12) . . . . ?
C21 C22 C23 C18 -0.35(18) . . . . ?
C23 N1 C17 O4 177.51(12) . . . . ?
C23 N1 C17 C11 -0.98(13) . . . . ?
C23 C18 C19 C20 -0.80(18) . . . . ?
C24 N1 C17 O4 1.8(2) . . . . ?
C24 N1 C17 C11 -176.73(11) . . . . ?
C24 N1 C23 C18 176.41(11) . . . . ?
C24 N1 C23 C22 -2.6(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 85.9 15.6 ?
