#------------------------------------------------------------------------------
#$Date: 2023-06-08 10:32:11 +0300 (Thu, 08 Jun 2023) $
#$Revision: 284400 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/73/8107308.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_8107308
loop_
_publ_author_name
'Liu, Juan'
'Chen, Sai'
'Wang, Meng'
'Yuan, Wei-Hua'
'Li, Honglei'
_publ_section_title
;
 The crystal structure of 3,7-dihydroxy-9-methoxy-4a-methyl-4aH-benzo[c]
 chromene-2,6-dione ---dichloromethane (1/1), C16H14Cl2O6
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1117
_journal_page_last               1118
_journal_paper_doi               10.1515/ncrs-2022-0418
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C15 H12 O6, C H2 Cl2'
_chemical_formula_sum            'C16 H14 Cl2 O6'
_chemical_formula_weight         373.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 115.942(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9847(19)
_cell_length_b                   18.284(4)
_cell_length_c                   11.107(3)
_cell_measurement_reflns_used    9082
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.23
_cell_volume                     1640.8(7)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9082
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.425
_exptl_absorpt_correction_T_max  0.8484
_exptl_absorpt_correction_T_min  0.7845
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0649P)²+0.9041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1358
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2691
_reflns_number_total             3381
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0418_suppl.cif
_cod_data_source_block           p21c
_cod_original_cell_volume        1640.7(7)
_cod_database_code               8107308
_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   0.848
_shelx_estimated_absorpt_t_min   0.785
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5A), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.3475(3) 0.64101(11) 0.67713(19) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.4069(3) 0.66159(13) 0.8211(2) 0.0474(5) Uani 1 1 d . . . . .
H2A H 0.462287 0.705694 0.851398 0.057 Uiso 1 1 calc R U . . .
C3 C 0.3822(3) 0.61821(13) 0.9068(2) 0.0441(5) Uani 1 1 d . . . . .
C4 C 0.3147(3) 0.54387(12) 0.8701(2) 0.0426(5) Uani 1 1 d . . . . .
C5 C 0.2807(3) 0.51836(12) 0.7355(2) 0.0406(5) Uani 1 1 d . . . . .
H5A H 0.243896 0.470670 0.710935 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3011(2) 0.56187(11) 0.64671(19) 0.0348(4) Uani 1 1 d . . . . .
C7 C 0.2779(3) 0.53801(11) 0.51289(19) 0.0354(4) Uani 1 1 d . . . . .
C8 C 0.1787(3) 0.48014(12) 0.4454(2) 0.0421(5) Uani 1 1 d . . . . .
H8 H 0.121254 0.454140 0.483687 0.051 Uiso 1 1 calc R U . . .
C9 C 0.1643(3) 0.46036(12) 0.3184(2) 0.0427(5) Uani 1 1 d . . . . .
C10 C 0.2483(3) 0.49823(12) 0.2598(2) 0.0446(5) Uani 1 1 d . . . . .
H10 H 0.237945 0.484940 0.175654 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3484(3) 0.55648(12) 0.3284(2) 0.0405(5) Uani 1 1 d . . . . .
C12 C 0.3643(3) 0.57801(11) 0.45461(19) 0.0363(4) Uani 1 1 d . . . . .
C13 C 0.4759(3) 0.63741(11) 0.5261(2) 0.0390(5) Uani 1 1 d . . . . .
C14 C 0.2025(3) 0.69049(13) 0.5913(2) 0.0531(6) Uani 1 1 d . . . . .
H14A H 0.236715 0.740707 0.607569 0.080 Uiso 1 1 calc R U . . .
H14B H 0.112252 0.682522 0.614027 0.080 Uiso 1 1 calc R U . . .
H14C H 0.167518 0.679309 0.498390 0.080 Uiso 1 1 calc R U . . .
C15 C 0.0447(4) 0.37962(17) 0.1308(3) 0.0668(8) Uani 1 1 d . . . . .
H15A H 0.002696 0.419544 0.068879 0.100 Uiso 1 1 calc R U . . .
H15B H -0.031350 0.339349 0.100190 0.100 Uiso 1 1 calc R U . . .
H15C H 0.150129 0.364629 0.136792 0.100 Uiso 1 1 calc R U . . .
O1 O 0.48593(19) 0.65877(8) 0.64487(14) 0.0428(4) Uani 1 1 d . . . . .
O2 O 0.4191(3) 0.64085(10) 1.03263(16) 0.0639(5) Uani 1 1 d . . . . .
H2 H 0.398690 0.607983 1.073400 0.096 Uiso 1 1 calc R U . . .
O3 O 0.2942(2) 0.50546(10) 0.95164(16) 0.0579(5) Uani 1 1 d . . . . .
O4 O 0.0637(2) 0.40260(10) 0.26065(16) 0.0569(5) Uani 1 1 d . . . . .
O5 O 0.4293(2) 0.59183(10) 0.26814(16) 0.0546(4) Uani 1 1 d . . . . .
H5 H 0.490919 0.622716 0.319255 0.082 Uiso 1 1 calc R U . . .
O6 O 0.5651(2) 0.66846(9) 0.48549(17) 0.0525(4) Uani 1 1 d . . . . .
C16 C -0.2044(4) 0.6940(2) 0.1712(3) 0.0839(10) Uani 1 1 d . . . . .
H16A H -0.286731 0.661832 0.106888 0.101 Uiso 1 1 calc R U . . .
H16B H -0.224726 0.743024 0.134180 0.101 Uiso 1 1 calc R U . . .
Cl1 Cl -0.22673(9) 0.69349(4) 0.32053(8) 0.0703(2) Uani 1 1 d . . . . .
Cl2 Cl -0.01065(12) 0.66619(7) 0.19446(9) 0.0991(4) 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 114.63(17) . .
C2 C1 C14 109.03(19) . .
C6 C1 C14 110.66(18) . .
O1 C1 C2 105.08(17) . .
O1 C1 C6 109.75(16) . .
O1 C1 C14 107.31(17) . .
C1 C2 H2A 119.3 . .
C3 C2 C1 121.5(2) . .
C3 C2 H2A 119.3 . .
C2 C3 C4 122.02(19) . .
C2 C3 O2 121.0(2) . .
O2 C3 C4 117.01(19) . .
C5 C4 C3 116.97(18) . .
O3 C4 C3 120.2(2) . .
O3 C4 C5 122.8(2) . .
C4 C5 H5A 119.1 . .
C6 C5 C4 121.8(2) . .
C6 C5 H5A 119.1 . .
C5 C6 C1 121.32(18) . .
C5 C6 C7 124.17(19) . .
C7 C6 C1 114.50(17) . .
C8 C7 C6 123.32(19) . .
C8 C7 C12 120.24(18) . .
C12 C7 C6 116.43(18) . .
C7 C8 H8 120.1 . .
C7 C8 C9 119.9(2) . .
C9 C8 H8 120.1 . .
C10 C9 C8 121.0(2) . .
O4 C9 C8 115.1(2) . .
O4 C9 C10 123.86(19) . .
C9 C10 H10 120.5 . .
C9 C10 C11 118.91(19) . .
C11 C10 H10 120.5 . .
C10 C11 C12 121.5(2) . .
O5 C11 C10 117.14(19) . .
O5 C11 C12 121.4(2) . .
C7 C12 C13 121.46(18) . .
C11 C12 C7 118.48(19) . .
C11 C12 C13 119.95(19) . .
O1 C13 C12 119.19(18) . .
O6 C13 C12 123.61(19) . .
O6 C13 O1 117.18(19) . .
C1 C14 H14A 109.5 . .
C1 C14 H14B 109.5 . .
C1 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O4 C15 H15A 109.5 . .
O4 C15 H15B 109.5 . .
O4 C15 H15C 109.5 . .
C13 O1 C1 118.34(16) . .
C3 O2 H2 109.5 . .
C9 O4 C15 117.7(2) . .
C11 O5 H5 109.5 . .
H16A C16 H16B 107.8 . .
Cl1 C16 H16A 109.1 . .
Cl1 C16 H16B 109.1 . .
Cl2 C16 H16A 109.1 . .
Cl2 C16 H16B 109.1 . .
Cl2 C16 Cl1 112.52(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.496(3) .
C1 C6 1.503(3) .
C1 C14 1.529(3) .
C1 O1 1.474(3) .
C2 H2A 0.9300 .
C2 C3 1.330(3) .
C3 C4 1.472(3) .
C3 O2 1.353(2) .
C4 C5 1.465(3) .
C4 O3 1.222(3) .
C5 H5A 0.9300 .
C5 C6 1.340(3) .
C6 C7 1.474(3) .
C7 C8 1.375(3) .
C7 C12 1.413(3) .
C8 H8 0.9300 .
C8 C9 1.407(3) .
C9 C10 1.379(3) .
C9 O4 1.355(3) .
C10 H10 0.9300 .
C10 C11 1.387(3) .
C11 C12 1.402(3) .
C11 O5 1.349(3) .
C12 C13 1.456(3) .
C13 O1 1.340(2) .
C13 O6 1.218(3) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C15 O4 1.439(3) .
O2 H2 0.8200 .
O5 H5 0.8200 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 Cl1 1.756(3) .
C16 Cl2 1.721(3) .
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
C1 C2 C3 C4 7.9(4) . . . .
C1 C2 C3 O2 -172.3(2) . . . .
C1 C6 C7 C8 -154.3(2) . . . .
C1 C6 C7 C12 25.7(3) . . . .
C2 C1 C6 C5 13.8(3) . . . .
C2 C1 C6 C7 -167.28(19) . . . .
C2 C1 O1 C13 171.68(17) . . . .
C2 C3 C4 C5 2.1(3) . . . .
C2 C3 C4 O3 179.7(2) . . . .
C3 C4 C5 C6 -3.6(3) . . . .
C4 C5 C6 C1 -4.8(3) . . . .
C4 C5 C6 C7 176.4(2) . . . .
C5 C6 C7 C8 24.5(3) . . . .
C5 C6 C7 C12 -155.4(2) . . . .
C6 C1 C2 C3 -15.4(3) . . . .
C6 C1 O1 C13 47.9(2) . . . .
C6 C7 C8 C9 -179.4(2) . . . .
C6 C7 C12 C11 178.85(18) . . . .
C6 C7 C12 C13 2.7(3) . . . .
C7 C8 C9 C10 -0.1(3) . . . .
C7 C8 C9 O4 179.9(2) . . . .
C7 C12 C13 O1 -5.9(3) . . . .
C7 C12 C13 O6 172.4(2) . . . .
C8 C7 C12 C11 -1.1(3) . . . .
C8 C7 C12 C13 -177.2(2) . . . .
C8 C9 C10 C11 0.2(3) . . . .
C8 C9 O4 C15 -179.7(2) . . . .
C9 C10 C11 C12 -0.8(3) . . . .
C9 C10 C11 O5 179.6(2) . . . .
C10 C9 O4 C15 0.3(3) . . . .
C10 C11 C12 C7 1.2(3) . . . .
C10 C11 C12 C13 177.4(2) . . . .
C11 C12 C13 O1 178.03(19) . . . .
C11 C12 C13 O6 -3.7(3) . . . .
C12 C7 C8 C9 0.5(3) . . . .
C12 C13 O1 C1 -21.1(3) . . . .
C14 C1 C2 C3 109.2(3) . . . .
C14 C1 C6 C5 -110.0(2) . . . .
C14 C1 C6 C7 68.9(2) . . . .
C14 C1 O1 C13 -72.4(2) . . . .
O1 C1 C2 C3 -136.0(2) . . . .
O1 C1 C6 C5 131.8(2) . . . .
O1 C1 C6 C7 -49.3(2) . . . .
O2 C3 C4 C5 -177.7(2) . . . .
O2 C3 C4 O3 0.0(3) . . . .
O3 C4 C5 C6 178.8(2) . . . .
O4 C9 C10 C11 -179.8(2) . . . .
O5 C11 C12 C7 -179.15(19) . . . .
O5 C11 C12 C13 -3.0(3) . . . .
O6 C13 O1 C1 160.47(19) . . . .
