#------------------------------------------------------------------------------
#$Date: 2020-05-28 00:51:21 +0300 (Thu, 28 May 2020) $
#$Revision: 252390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/77/4517722.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_4517722
loop_
_publ_author_name
'Farias, Kaio'
'da Costa, Roner F.'
'Meira, Assuero S.'
'Diniz-Filho, Jairo'
'Bezerra, Eveline M.'
'Freire, Valder N.'
'Guest, Prue'
'Nikahd, Maryam'
'Ma, Xinghua'
'Gardiner, Michael G.'
'Banwell, Martin G.'
'de Oliveira, Maria da C. F.'
'de Moraes, Manoel O.'
'do Ó Pessoa, Claudia'
_publ_section_title
;
 Antitumor Potential of the Isoflavonoids (+)- and
 (−)-2,3,9-Trimethoxypterocarpan: Mechanism-of-Action Studies
;
_journal_name_full               'ACS Medicinal Chemistry Letters'
_journal_paper_doi               10.1021/acsmedchemlett.0c00097
_journal_year                    2020
_chemical_formula_moiety         'C22 H24 O6'
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41
_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     dual
_audit_creation_date             2020-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.836(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0596(19)
_cell_length_b                   4.9375(7)
_cell_length_c                   24.003(3)
_cell_measurement_reflns_used    490
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      58.7910
_cell_measurement_theta_min      5.9810
_cell_volume                     1839.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00  130.00    --  -36.84 125.00-150.00   81
  2  ω   -103.00 -56.00   1.00  130.00    --  -36.84 -38.00  60.00   47
  3  ω    -53.00 -18.00   1.00  130.00    --  -36.84 -38.00  60.00   35
  4  ω     28.00 111.00   1.00  180.00    --   84.62-125.00 -30.00   83
  5  ω     64.00 154.00   1.00  180.00    --   84.62  30.00  90.00   90
  6  ω     50.00 102.00   1.00  180.00    --   84.62 -61.00 -60.00   52
  7  ω     28.00 111.00   1.00  180.00    --   84.62-125.00-180.00   83
  8  ω     70.00 140.00   1.00  180.00    --   84.62  15.00  30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0209595000
_diffrn_orient_matrix_UB_12      -0.2846536000
_diffrn_orient_matrix_UB_13      0.0190518000
_diffrn_orient_matrix_UB_21      0.0680652000
_diffrn_orient_matrix_UB_22      -0.1232807000
_diffrn_orient_matrix_UB_23      -0.0274771000
_diffrn_orient_matrix_UB_31      0.0689539000
_diffrn_orient_matrix_UB_32      0.0352731000
_diffrn_orient_matrix_UB_33      0.0574059000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.1482
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4792
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        61.069
_diffrn_reflns_theta_max         61.069
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_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     257
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0762
_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)+(0.0360P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1392
_reflns_number_total             2751
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ml0c00097_si_003.cif
_cod_data_source_block           mn-fc-178scaled
_cod_database_code               4517722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H24 O6 '
_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.
;
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C17(H17), C22(H22)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_ins_header
;
TITL MN-FC-178scaled in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  16.059572   4.937543  24.002774  90.0000 104.8364  90.0000
ZERR    4.00   0.001872   0.000726   0.003341   0.0000   0.0115   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H O
UNIT 88.00 96.00 24.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-01-28
_olex2_date_sample_submission    2019-12-10
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder with oil'
_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.640
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
O1 O 0.8572(2) 0.1006(8) 0.20446(15) 0.0369(10) Uani 1 1 d . . . . .
O2 O 0.5763(2) -0.2682(8) 0.11782(15) 0.0357(10) Uani 1 1 d . . . . .
O3 O 0.5033(2) 0.0633(8) 0.17285(16) 0.0365(10) Uani 1 1 d . . . . .
O4 O 0.9523(2) 0.6852(8) 0.39562(16) 0.0384(11) Uani 1 1 d . . . . .
O5 O 0.7836(2) 0.9596(9) 0.52475(17) 0.0442(12) Uani 1 1 d . . . . .
O6 O 0.6666(2) 0.6077(9) 0.48205(17) 0.0464(12) Uani 1 1 d . . . . .
C1 C 0.8948(3) 0.3634(13) 0.2186(2) 0.0377(15) Uani 1 1 d . . . . .
H1A H 0.870494 0.487321 0.187324 0.045 Uiso 1 1 calc R . . . .
H1B H 0.956251 0.351843 0.222272 0.045 Uiso 1 1 calc R . . . .
C2 C 0.8804(3) 0.4753(13) 0.2734(2) 0.0369(16) Uani 1 1 d . . . . .
H2 H 0.900256 0.663217 0.279516 0.044 Uiso 1 1 calc R . . . .
C3 C 0.7863(3) 0.4461(12) 0.2784(2) 0.0319(15) Uani 1 1 d . . . . .
H3 H 0.758655 0.620689 0.281252 0.038 Uiso 1 1 calc R . . . .
C4 C 0.7321(3) 0.2628(12) 0.2329(2) 0.0306(14) Uani 1 1 d . . . . .
C5 C 0.7680(3) 0.0964(12) 0.2000(2) 0.0311(14) Uani 1 1 d . . . . .
C6 C 0.6409(3) 0.2544(12) 0.2245(2) 0.0323(14) Uani 1 1 d . . . . .
H6 H 0.614479 0.368024 0.245751 0.039 Uiso 1 1 calc R . . . .
C7 C 0.5931(3) 0.0820(11) 0.1859(2) 0.0290(14) Uani 1 1 d . . . . .
C8 C 0.4606(4) 0.2940(13) 0.1892(3) 0.0418(16) Uani 1 1 d . . . . .
H8A H 0.478957 0.455165 0.173369 0.063 Uiso 1 1 calc GR . . . .
H8B H 0.474790 0.307653 0.230427 0.063 Uiso 1 1 calc GR . . . .
H8C H 0.399405 0.273479 0.174628 0.063 Uiso 1 1 calc GR . . . .
C9 C 0.6306(3) -0.0983(12) 0.1544(2) 0.0299(14) Uani 1 1 d . . . . .
C10 C 0.6130(4) -0.4530(12) 0.0851(2) 0.0408(16) Uani 1 1 d . . . . .
H10A H 0.639660 -0.353610 0.059962 0.061 Uiso 1 1 calc GR . . . .
H10B H 0.568519 -0.567132 0.062586 0.061 Uiso 1 1 calc GR . . . .
H10C H 0.655393 -0.562644 0.110753 0.061 Uiso 1 1 calc GR . . . .
C11 C 0.7205(3) -0.0843(12) 0.1604(2) 0.0306(14) Uani 1 1 d . . . . .
H11 H 0.746813 -0.193449 0.138285 0.037 Uiso 1 1 calc R . . . .
C12 C 0.9811(3) 0.4324(13) 0.3771(2) 0.0367(16) Uani 1 1 d . . . . .
H12A H 0.995050 0.307856 0.409392 0.044 Uiso 1 1 calc R . . . .
H12B H 1.033063 0.463346 0.364496 0.044 Uiso 1 1 calc R . . . .
C13 C 0.9132(3) 0.3049(12) 0.3282(2) 0.0333(15) Uani 1 1 d . . . . .
H13 H 0.930494 0.123266 0.318995 0.040 Uiso 1 1 calc R . . . .
C14 C 0.8222(3) 0.3024(12) 0.3393(2) 0.0316(15) Uani 1 1 d . . . . .
H14 H 0.799403 0.118884 0.340410 0.038 Uiso 1 1 calc R . . . .
C15 C 0.8154(3) 0.4695(12) 0.3893(2) 0.0299(14) Uani 1 1 d . . . . .
C16 C 0.8784(3) 0.6595(12) 0.4147(2) 0.0315(14) Uani 1 1 d . . . . .
C17 C 0.7432(3) 0.4537(13) 0.4120(2) 0.0346(15) Uani 1 1 d . . . . .
H17 H 0.700160 0.329008 0.396329 0.041 Uiso 1 1 calc R . . . .
C18 C 0.7339(3) 0.6158(13) 0.4563(2) 0.0355(15) Uani 1 1 d . . . . .
C19 C 0.6047(3) 0.3977(13) 0.4633(2) 0.0452(17) Uani 1 1 d . . . . .
H19A H 0.575766 0.424738 0.423433 0.068 Uiso 1 1 calc GR . . . .
H19B H 0.563322 0.401740 0.485942 0.068 Uiso 1 1 calc GR . . . .
H19C H 0.633297 0.225353 0.467915 0.068 Uiso 1 1 calc GR . . . .
C20 C 0.7984(4) 0.8087(13) 0.4803(2) 0.0381(16) Uani 1 1 d . . . . .
C21 C 0.8467(4) 1.1530(12) 0.5507(3) 0.0449(17) Uani 1 1 d . . . . .
H21A H 0.856908 1.273309 0.521762 0.067 Uiso 1 1 calc GR . . . .
H21B H 0.899340 1.061740 0.569262 0.067 Uiso 1 1 calc GR . . . .
H21C H 0.826799 1.255007 0.578832 0.067 Uiso 1 1 calc GR . . . .
C22 C 0.8705(3) 0.8239(11) 0.4595(2) 0.0272(13) Uani 1 1 d . . . . .
H22 H 0.914050 0.945990 0.475623 0.033 Uiso 1 1 calc R . . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 4 0.0070
5 0 -4 0.0094
3 0 5 0.0070
-3 0 -5 0.0094
-2 3 2 0.0802
2 -3 -2 0.0802
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
C5 O1 C1 112.9(4) . . ?
C9 O2 C10 117.7(4) . . ?
C7 O3 C8 115.1(4) . . ?
C16 O4 C12 113.1(5) . . ?
C20 O5 C21 117.5(5) . . ?
C18 O6 C19 116.3(5) . . ?
O1 C1 C2 113.0(5) . . ?
C1 C2 C3 113.9(4) . . ?
C1 C2 C13 116.9(5) . . ?
C13 C2 C3 90.6(4) . . ?
C2 C3 C14 88.9(4) . . ?
C4 C3 C2 113.1(5) . . ?
C4 C3 C14 113.7(5) . . ?
C5 C4 C3 121.8(5) . . ?
C5 C4 C6 118.2(5) . . ?
C6 C4 C3 120.0(5) . . ?
C4 C5 O1 121.3(5) . . ?
C4 C5 C11 123.1(5) . . ?
C11 C5 O1 115.7(5) . . ?
C7 C6 C4 119.9(5) . . ?
O3 C7 C9 113.4(5) . . ?
C6 C7 O3 124.8(5) . . ?
C6 C7 C9 121.8(5) . . ?
O2 C9 C7 116.7(5) . . ?
O2 C9 C11 124.4(5) . . ?
C7 C9 C11 118.9(5) . . ?
C5 C11 C9 118.0(5) . . ?
O4 C12 C13 112.0(4) . . ?
C2 C13 C14 91.1(4) . . ?
C12 C13 C2 117.1(5) . . ?
C12 C13 C14 113.0(5) . . ?
C13 C14 C3 88.5(4) . . ?
C15 C14 C3 114.2(5) . . ?
C15 C14 C13 113.8(5) . . ?
C16 C15 C14 122.0(5) . . ?
C16 C15 C17 116.5(5) . . ?
C17 C15 C14 121.5(5) . . ?
O4 C16 C15 120.2(5) . . ?
C22 C16 O4 117.6(5) . . ?
C22 C16 C15 122.2(5) . . ?
C18 C17 C15 122.3(5) . . ?
O6 C18 C20 114.4(5) . . ?
C17 C18 O6 125.9(5) . . ?
C17 C18 C20 119.7(5) . . ?
O5 C20 C18 115.3(5) . . ?
O5 C20 C22 125.7(5) . . ?
C22 C20 C18 119.0(6) . . ?
C20 C22 C16 120.4(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
O1 C1 1.435(7) . ?
O1 C5 1.408(6) . ?
O2 C9 1.358(6) . ?
O2 C10 1.426(6) . ?
O3 C7 1.399(6) . ?
O3 C8 1.435(7) . ?
O4 C12 1.440(7) . ?
O4 C16 1.383(6) . ?
O5 C20 1.370(7) . ?
O5 C21 1.416(6) . ?
O6 C18 1.376(7) . ?
O6 C19 1.427(7) . ?
C1 C2 1.498(8) . ?
C2 C3 1.553(7) . ?
C2 C13 1.536(7) . ?
C3 C4 1.511(7) . ?
C3 C14 1.595(7) . ?
C4 C5 1.365(8) . ?
C4 C6 1.427(7) . ?
C5 C11 1.382(7) . ?
C6 C7 1.344(7) . ?
C7 C9 1.399(7) . ?
C9 C11 1.416(7) . ?
C12 C13 1.519(7) . ?
C13 C14 1.552(7) . ?
C14 C15 1.484(8) . ?
C15 C16 1.401(8) . ?
C15 C17 1.403(7) . ?
C16 C22 1.378(7) . ?
C17 C18 1.370(8) . ?
C18 C20 1.417(8) . ?
C20 C22 1.375(7) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0032 -0.0020 4.0012 0.1817 -0.4502 -0.1154
5.0032 0.0020 -4.0012 -0.1817 0.4502 0.1154
3.0004 -0.0044 4.9933 0.0335 0.0676 0.4934
-3.0004 0.0044 -4.9933 -0.0335 -0.0676 -0.4934
-2.0143 2.9933 2.0568 -0.7707 -0.5626 0.0848
2.0143 -2.9933 -2.0568 0.7707 0.5626 -0.0848
