#------------------------------------------------------------------------------
#$Date: 2020-08-01 02:13:44 +0300 (Sat, 01 Aug 2020) $
#$Revision: 254712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/86/4038634.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_4038634
loop_
_publ_author_name
'Joshi, Dirgha Raj'
'Seo, Yohan'
'Heo, Yunkyung'
'Park, So-Hyeon'
'Lee, Yechan'
'Namkung, Wan'
'Kim, Ikyon'
_publ_section_title
;
 Domino [4+2] Annulation Access to Quinone-Indolizine Hybrids: Anticancer
 N-Fused Polycycles.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01291
_journal_year                    2020
_chemical_formula_moiety         'C20 H12 Cl N O4'
_chemical_formula_sum            'C20 H12 Cl N O4'
_chemical_formula_weight         365.76
_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             2020-01-03
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:19:11 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                96.365(3)
_cell_angle_beta                 98.489(3)
_cell_angle_gamma                108.418(4)
_cell_formula_units_Z            2
_cell_length_a                   8.2755(3)
_cell_length_b                   10.0566(4)
_cell_length_c                   14.2145(6)
_cell_measurement_reflns_used    7518
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0680
_cell_measurement_theta_min      2.7520
_cell_volume                     1094.34(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (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 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2262
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -45.00  14.00   1.00    8.78    --  -11.20  81.00 -53.00   59
  2  ω    -36.00 -11.00   1.00    8.78    --  -11.20 -81.00-176.00   25
  3  ω    -33.00  45.00   1.00    8.78    --   11.83 -81.00-176.00   78
  4  ω    -66.00  21.00   1.00    8.78    --  -11.20 -77.00  90.00   87
  5  ω    -64.00  44.00   1.00    8.78    --   11.83 -77.00  30.00  108
  6  ω    -15.00  75.00   1.00    8.78    --   11.83  57.00  90.00   90
  7  ω    -13.00  86.00   1.00    8.78    --   11.83  38.00 -90.00   99
  8  ω    -20.00  53.00   1.00    8.78    --   11.83 -99.00 -90.00   73
  9  ω    -12.00  53.00   1.00    8.78    --   11.83 -99.00 150.00   65
 10  ω    -13.00  83.00   1.00    8.78    --   11.83  38.00   0.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0885396000
_diffrn_orient_matrix_UB_12      0.0405594000
_diffrn_orient_matrix_UB_13      0.0185740000
_diffrn_orient_matrix_UB_21      -0.0237841000
_diffrn_orient_matrix_UB_22      0.0325156000
_diffrn_orient_matrix_UB_23      0.0401046000
_diffrn_orient_matrix_UB_31      0.0086090000
_diffrn_orient_matrix_UB_32      -0.0546264000
_diffrn_orient_matrix_UB_33      0.0258044000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22937
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light pink'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0967P)²+0.6182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1782
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4017
_reflns_number_total             4972
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01291_si_002.cif
_cod_data_source_block           exp_1418
_cod_database_code               4038634
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C24 H12 Cl N O6'
_chemical_oxdiff_usercomment     DR-327
_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   0.980
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C11(H11), C20(H20), C4(H4), C5(H5), C2(H2), C19(H19), C18(H18),
 C3(H3)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2020-01-02
_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 2.281
_oxdiff_exptl_absorpt_empirical_full_min 0.438
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
Cl1 Cl 0.42718(8) 1.14956(6) 0.85317(5) 0.03454(19) Uani 1 1 d . . . . .
O1 O 0.23195(18) 0.45039(15) 0.86600(10) 0.0187(3) Uani 1 1 d . . . . .
O4 O 0.2115(2) 0.27250(16) 0.35365(10) 0.0225(3) Uani 1 1 d . . . . .
O2 O 0.09372(19) 0.45987(16) 0.64670(10) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.5040(2) 0.26621(18) 0.44953(11) 0.0281(4) Uani 1 1 d . . . . .
N1 N 0.5678(2) 0.46645(17) 0.79639(11) 0.0152(3) Uani 1 1 d . . . . .
C7 C 0.3119(2) 0.5268(2) 0.81462(13) 0.0157(4) Uani 1 1 d . . . . .
C9 C 0.3587(2) 0.4162(2) 0.65297(13) 0.0146(4) Uani 1 1 d . . . . .
C15 C 0.4690(3) 0.3647(2) 0.60099(14) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.3378(2) 0.6806(2) 0.82275(14) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.4099(2) 0.4666(2) 0.74934(14) 0.0155(4) Uani 1 1 d . . . . .
C16 C 0.6264(3) 0.3656(2) 0.64824(15) 0.0181(4) Uani 1 1 d . . . . .
H16 H 0.699235 0.331868 0.613506 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6802(3) 0.4163(2) 0.74793(15) 0.0179(4) Uani 1 1 d . . . . .
C11 C 0.1441(3) 0.3707(2) 0.49836(14) 0.0179(4) Uani 1 1 d . . . . .
H11 H 0.038721 0.375322 0.464317 0.022 Uiso 1 1 calc R U . . .
C10 C 0.1903(3) 0.4184(2) 0.60211(14) 0.0165(4) Uani 1 1 d . . . . .
C20 C 0.6462(3) 0.5131(2) 0.89211(14) 0.0183(4) Uani 1 1 d . . . . .
H20 H 0.599331 0.552284 0.940937 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4221(3) 0.7600(2) 0.75856(15) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.461728 0.715108 0.708803 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2830(3) 0.7477(2) 0.89700(14) 0.0197(4) Uani 1 1 d . . . . .
H5 H 0.227009 0.694021 0.941132 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4152(3) 0.3125(2) 0.49627(15) 0.0198(4) Uani 1 1 d . . . . .
C2 C 0.3098(3) 0.8914(2) 0.90657(15) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.272385 0.937326 0.956856 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2447(3) 0.3201(2) 0.44852(14) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.8033(3) 0.4930(2) 0.90438(15) 0.0213(4) Uani 1 1 d . . . . .
H19 H 0.884295 0.516337 0.963568 0.026 Uiso 1 1 calc R U . . .
C18 C 0.8259(3) 0.4326(2) 0.81564(15) 0.0218(4) Uani 1 1 d . . . . .
H18 H 0.923547 0.407448 0.804236 0.026 Uiso 1 1 calc R U . . .
C1 C 0.3928(3) 0.9681(2) 0.84108(16) 0.0228(5) Uani 1 1 d . . . . .
C3 C 0.4478(3) 0.9043(2) 0.76757(15) 0.0233(5) Uani 1 1 d . . . . .
H3 H 0.502879 0.958506 0.723380 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0460(3) 0.2667(2) 0.30022(15) 0.0246(5) Uani 1 1 d . . . . .
H12A H 0.037935 0.234318 0.231519 0.037 Uiso 1 1 calc R U . . .
H12B H 0.035836 0.361536 0.309135 0.037 Uiso 1 1 calc R U . . .
H12C H -0.047857 0.200251 0.323754 0.037 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'
Cl Cl 0.1484 0.1585 '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 O4 C12 116.57(16) . . ?
C8 N1 C17 122.32(16) . . ?
C20 N1 C8 129.31(17) . . ?
C20 N1 C17 108.36(16) . . ?
O1 C7 C6 123.27(18) . . ?
O1 C7 C8 118.51(17) . . ?
C6 C7 C8 117.66(17) . . ?
C15 C9 C10 120.49(17) . . ?
C8 C9 C15 120.20(18) . . ?
C8 C9 C10 119.30(18) . . ?
C9 C15 C14 120.31(18) . . ?
C16 C15 C9 120.18(18) . . ?
C16 C15 C14 119.50(19) . . ?
C4 C6 C7 120.37(18) . . ?
C5 C6 C7 119.79(17) . . ?
C5 C6 C4 119.80(18) . . ?
N1 C8 C7 113.56(16) . . ?
C9 C8 N1 119.28(18) . . ?
C9 C8 C7 127.16(17) . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.18(19) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 N1 117.84(18) . . ?
C18 C17 N1 107.17(18) . . ?
C18 C17 C16 135.0(2) . . ?
C10 C11 H11 118.7 . . ?
C13 C11 H11 118.7 . . ?
C13 C11 C10 122.62(18) . . ?
O2 C10 C9 120.71(17) . . ?
O2 C10 C11 121.57(18) . . ?
C11 C10 C9 117.73(18) . . ?
N1 C20 H20 126.1 . . ?
C19 C20 N1 107.88(18) . . ?
C19 C20 H20 126.1 . . ?
C6 C4 H4 120.0 . . ?
C3 C4 C6 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C6 C5 H5 119.8 . . ?
C2 C5 C6 120.35(19) . . ?
C2 C5 H5 119.8 . . ?
O3 C14 C15 122.44(19) . . ?
O3 C14 C13 120.89(19) . . ?
C15 C14 C13 116.66(18) . . ?
C5 C2 H2 120.6 . . ?
C5 C2 C1 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
O4 C13 C11 126.63(18) . . ?
O4 C13 C14 111.23(17) . . ?
C11 C13 C14 122.14(18) . . ?
C20 C19 H19 125.4 . . ?
C20 C19 C18 109.12(18) . . ?
C18 C19 H19 125.4 . . ?
C17 C18 C19 107.47(19) . . ?
C17 C18 H18 126.3 . . ?
C19 C18 H18 126.3 . . ?
C2 C1 Cl1 118.90(17) . . ?
C3 C1 Cl1 119.29(16) . . ?
C3 C1 C2 121.80(19) . . ?
C4 C3 H3 120.3 . . ?
C1 C3 C4 119.30(19) . . ?
C1 C3 H3 120.3 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 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
Cl1 C1 1.740(2) . ?
O1 C7 1.228(2) . ?
O4 C13 1.337(2) . ?
O4 C12 1.445(3) . ?
O2 C10 1.231(3) . ?
O3 C14 1.221(3) . ?
N1 C8 1.378(2) . ?
N1 C17 1.415(3) . ?
N1 C20 1.378(2) . ?
C7 C6 1.482(3) . ?
C7 C8 1.514(3) . ?
C9 C15 1.435(3) . ?
C9 C8 1.361(3) . ?
C9 C10 1.480(3) . ?
C15 C16 1.372(3) . ?
C15 C14 1.474(3) . ?
C6 C4 1.398(3) . ?
C6 C5 1.397(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(3) . ?
C17 C18 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.453(3) . ?
C11 C13 1.348(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.367(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C2 1.379(3) . ?
C14 C13 1.501(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.396(3) . ?
C19 H19 0.9500 . ?
C19 C18 1.402(3) . ?
C18 H18 0.9500 . ?
C1 C3 1.374(3) . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
Cl1 C1 C3 C4 179.30(16) . . . . ?
O1 C7 C6 C4 -176.54(18) . . . . ?
O1 C7 C6 C5 5.6(3) . . . . ?
O1 C7 C8 N1 -79.6(2) . . . . ?
O1 C7 C8 C9 100.9(2) . . . . ?
O3 C14 C13 O4 -0.5(3) . . . . ?
O3 C14 C13 C11 179.99(19) . . . . ?
N1 C17 C18 C19 -0.4(2) . . . . ?
N1 C20 C19 C18 -0.1(2) . . . . ?
C7 C6 C4 C3 -179.15(18) . . . . ?
C7 C6 C5 C2 178.61(18) . . . . ?
C9 C15 C16 C17 0.3(3) . . . . ?
C9 C15 C14 O3 -179.11(19) . . . . ?
C9 C15 C14 C13 1.6(3) . . . . ?
C15 C9 C8 N1 -0.5(3) . . . . ?
C15 C9 C8 C7 178.93(18) . . . . ?
C15 C9 C10 O2 178.57(18) . . . . ?
C15 C9 C10 C11 -1.7(3) . . . . ?
C15 C16 C17 N1 -0.5(3) . . . . ?
C15 C16 C17 C18 -179.5(2) . . . . ?
C15 C14 C13 O4 178.82(16) . . . . ?
C15 C14 C13 C11 -0.7(3) . . . . ?
C6 C7 C8 N1 92.2(2) . . . . ?
C6 C7 C8 C9 -87.3(2) . . . . ?
C6 C4 C3 C1 1.3(3) . . . . ?
C6 C5 C2 C1 -0.2(3) . . . . ?
C8 N1 C17 C16 0.1(3) . . . . ?
C8 N1 C17 C18 179.40(17) . . . . ?
C8 N1 C20 C19 -179.10(18) . . . . ?
C8 C7 C6 C4 12.2(3) . . . . ?
C8 C7 C6 C5 -165.67(17) . . . . ?
C8 C9 C15 C16 0.2(3) . . . . ?
C8 C9 C15 C14 -178.91(18) . . . . ?
C8 C9 C10 O2 -2.9(3) . . . . ?
C8 C9 C10 C11 176.84(17) . . . . ?
C16 C15 C14 O3 1.8(3) . . . . ?
C16 C15 C14 C13 -177.55(17) . . . . ?
C16 C17 C18 C19 178.6(2) . . . . ?
C17 N1 C8 C7 -179.17(16) . . . . ?
C17 N1 C8 C9 0.4(3) . . . . ?
C17 N1 C20 C19 -0.1(2) . . . . ?
C10 C9 C15 C16 178.73(17) . . . . ?
C10 C9 C15 C14 -0.4(3) . . . . ?
C10 C9 C8 N1 -179.08(16) . . . . ?
C10 C9 C8 C7 0.4(3) . . . . ?
C10 C11 C13 O4 179.10(18) . . . . ?
C10 C11 C13 C14 -1.5(3) . . . . ?
C20 N1 C8 C7 -0.3(3) . . . . ?
C20 N1 C8 C9 179.20(18) . . . . ?
C20 N1 C17 C16 -178.91(17) . . . . ?
C20 N1 C17 C18 0.4(2) . . . . ?
C20 C19 C18 C17 0.4(2) . . . . ?
C4 C6 C5 C2 0.8(3) . . . . ?
C5 C6 C4 C3 -1.3(3) . . . . ?
C5 C2 C1 Cl1 -179.85(16) . . . . ?
C5 C2 C1 C3 0.2(3) . . . . ?
C14 C15 C16 C17 179.43(18) . . . . ?
C2 C1 C3 C4 -0.7(3) . . . . ?
C13 C11 C10 O2 -177.60(19) . . . . ?
C13 C11 C10 C9 2.7(3) . . . . ?
C12 O4 C13 C11 -4.0(3) . . . . ?
C12 O4 C13 C14 176.52(16) . . . . ?
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 -0.160 0.000 -0.622 360.6 99.1 ?
