#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/32/7123238.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_7123238
loop_
_publ_author_name
'Harrowven, David'
'Vendeville, Jean-Baptiste'
'Matters, Rebecca'
'Chen, Anqi'
'Tizzard, Graham J.'
'Light, Mark E.'
'Chai, Christina L. L.'
_publ_section_title
;
 A Synthetic Approach to Chrysophaentin F
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01666J
_journal_year                    2019
_chemical_compound_source        'Jean-Baptiste Vendeville'
_chemical_formula_sum            'C20 H22 O7'
_chemical_formula_weight         374.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2019-02-21 deposited with the CCDC.    2019-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.966(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.898(3)
_cell_length_b                   16.287(4)
_cell_length_c                   8.832(2)
_cell_measurement_reflns_used    4223
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.9
_cell_volume                     1832.7(7)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8404
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chip
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0404P)²+0.2319P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                3012
_reflns_number_total             4165
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c9cc01666j2.cif
_cod_data_source_block           2012sot0077
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1832.8(8)
_cod_original_sg_symbol_H-M      'P 21/C'
_cod_database_code               7123238
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.8001(2) 0.54032(15) 0.4136(3) 0.0351(6) Uani 1 1 d .
H2 H 0.8724 0.5373 0.4676 0.053 Uiso 1 1 calc R
H3 H 0.7733 0.5962 0.4211 0.053 Uiso 1 1 calc R
H1 H 0.7988 0.5261 0.3055 0.053 Uiso 1 1 calc R
C2 C 0.76011(17) 0.40362(14) 0.4719(2) 0.0219(5) Uani 1 1 d .
C3 C 0.69139(16) 0.34940(13) 0.5488(2) 0.0189(5) Uani 1 1 d .
C4 C 0.61346(16) 0.38199(14) 0.6241(2) 0.0198(5) Uani 1 1 d .
H5 H 0.6032 0.4397 0.6279 0.024 Uiso 1 1 calc R
C5 C 0.55103(17) 0.32872(13) 0.6937(2) 0.0203(5) Uani 1 1 d .
C6 C 0.56593(16) 0.24419(13) 0.6856(2) 0.0183(5) Uani 1 1 d .
C7 C 0.64409(17) 0.21232(13) 0.6097(2) 0.0187(5) Uani 1 1 d .
C8 C 0.70794(16) 0.26525(13) 0.5422(2) 0.0194(5) Uani 1 1 d .
H4 H 0.7623 0.2442 0.4920 0.023 Uiso 1 1 calc R
C9 C 0.46334(19) 0.43884(14) 0.8014(3) 0.0293(6) Uani 1 1 d .
H6 H 0.5313 0.4601 0.8510 0.044 Uiso 1 1 calc R
H8 H 0.4108 0.4472 0.8690 0.044 Uiso 1 1 calc R
H7 H 0.4416 0.4680 0.7046 0.044 Uiso 1 1 calc R
C10 C 0.73710(18) 0.09528(14) 0.5439(3) 0.0264(5) Uani 1 1 d .
H10 H 0.7322 0.1128 0.4369 0.040 Uiso 1 1 calc R
H11 H 0.7348 0.0352 0.5486 0.040 Uiso 1 1 calc R
H9 H 0.8033 0.1149 0.6024 0.040 Uiso 1 1 calc R
C11 C 0.40835(16) 0.17015(12) 0.6901(2) 0.0180(5) Uani 1 1 d .
C12 C 0.36043(16) 0.20352(13) 0.5534(2) 0.0176(5) Uani 1 1 d .
H12 H 0.3960 0.2435 0.5022 0.021 Uiso 1 1 calc R
C13 C 0.25937(16) 0.17834(13) 0.4906(2) 0.0182(5) Uani 1 1 d .
C14 C 0.20876(16) 0.11974(13) 0.5658(2) 0.0181(5) Uani 1 1 d .
C15 C 0.25751(17) 0.08599(13) 0.7032(2) 0.0213(5) Uani 1 1 d .
H14 H 0.2226 0.0454 0.7539 0.026 Uiso 1 1 calc R
C16 C 0.35704(17) 0.11188(13) 0.7656(2) 0.0194(5) Uani 1 1 d .
H13 H 0.3903 0.0897 0.8604 0.023 Uiso 1 1 calc R
C17 C 0.20327(17) 0.21390(14) 0.3433(2) 0.0232(5) Uani 1 1 d .
H15 H 0.1790 0.2701 0.3621 0.028 Uiso 1 1 calc R
H01B H 0.2524 0.2175 0.2679 0.028 Uiso 1 1 calc R
C18 C 0.05096(17) 0.14220(14) 0.3915(2) 0.0215(5) Uani 1 1 d .
C19 C 0.00955(18) 0.21561(15) 0.4682(3) 0.0300(6) Uani 1 1 d .
H16 H 0.0683 0.2453 0.5279 0.045 Uiso 1 1 calc R
H18 H -0.0387 0.1970 0.5366 0.045 Uiso 1 1 calc R
H17 H -0.0278 0.2522 0.3900 0.045 Uiso 1 1 calc R
C20 C -0.03442(18) 0.08788(14) 0.3092(3) 0.0296(6) Uani 1 1 d .
H19 H -0.0787 0.1198 0.2300 0.044 Uiso 1 1 calc R
H20 H -0.0774 0.0666 0.3826 0.044 Uiso 1 1 calc R
H02C H -0.0027 0.0419 0.2613 0.044 Uiso 1 1 calc R
O1 O 0.73505(13) 0.48340(9) 0.48215(17) 0.0274(4) Uani 1 1 d .
O2 O 0.83134(12) 0.38007(10) 0.40835(17) 0.0284(4) Uani 1 1 d .
O3 O 0.47259(12) 0.35264(9) 0.77125(17) 0.0249(4) Uani 1 1 d .
O4 O 0.65106(12) 0.12871(9) 0.60792(16) 0.0241(4) Uani 1 1 d .
O5 O 0.50854(11) 0.19119(9) 0.76144(15) 0.0206(3) Uani 1 1 d .
O6 O 0.11521(12) 0.16435(9) 0.28198(16) 0.0228(4) Uani 1 1 d .
O7 O 0.11073(11) 0.09055(9) 0.50674(16) 0.0227(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'
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
O2 C2 O1 123.0(2)
O2 C2 C3 124.9(2)
O1 C2 C3 112.1(2)
C8 C3 C4 121.5(2)
C8 C3 C2 117.3(2)
C4 C3 C2 121.1(2)
C5 C4 C3 118.9(2)
O3 C5 C4 124.7(2)
O3 C5 C6 115.28(19)
C4 C5 C6 120.0(2)
O5 C6 C5 120.3(2)
O5 C6 C7 118.9(2)
C5 C6 C7 120.6(2)
O4 C7 C8 124.7(2)
O4 C7 C6 115.52(19)
C8 C7 C6 119.8(2)
C7 C8 C3 119.2(2)
C12 C11 C16 120.58(19)
C12 C11 O5 123.92(19)
C16 C11 O5 115.50(18)
C11 C12 C13 119.68(19)
C14 C13 C12 119.53(18)
C14 C13 C17 118.83(19)
C12 C13 C17 121.63(19)
O7 C14 C13 122.06(18)
O7 C14 C15 117.30(19)
C13 C14 C15 120.61(19)
C16 C15 C14 119.6(2)
C15 C16 C11 120.04(19)
O6 C17 C13 110.94(17)
O6 C18 O7 108.93(17)
O6 C18 C20 106.32(18)
O7 C18 C20 105.50(17)
O6 C18 C19 112.96(19)
O7 C18 C19 109.35(17)
C20 C18 C19 113.43(19)
C2 O1 C1 115.46(19)
C5 O3 C9 117.47(17)
C7 O4 C10 116.19(17)
C6 O5 C11 117.79(15)
C18 O6 C17 113.59(16)
C14 O7 C18 115.06(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.445(3)
C2 O2 1.211(3)
C2 O1 1.345(3)
C2 C3 1.489(3)
C3 C8 1.390(3)
C3 C4 1.394(3)
C4 C5 1.390(3)
C5 O3 1.364(2)
C5 C6 1.394(3)
C6 O5 1.377(2)
C6 C7 1.395(3)
C7 O4 1.365(2)
C7 C8 1.390(3)
C9 O3 1.437(2)
C10 O4 1.429(3)
C11 C12 1.379(3)
C11 C16 1.386(3)
C11 O5 1.389(2)
C12 C13 1.396(3)
C13 C14 1.384(3)
C13 C17 1.503(3)
C14 O7 1.375(2)
C14 C15 1.390(3)
C15 C16 1.382(3)
C17 O6 1.429(2)
C18 O6 1.415(3)
C18 O7 1.447(2)
C18 C20 1.508(3)
C18 C19 1.512(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189690
