#------------------------------------------------------------------------------
#$Date: 2019-11-11 21:23:54 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227409 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/60/4036035.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_4036035
loop_
_publ_author_name
'Sako, Makoto'
'Aoki, Takanori'
'Zumbrägel, Nadine'
'Schober, Lukas'
'Gröger, Harald'
'Takizawa, Shinobu'
'Sasai, Hiroaki'
_publ_section_title
;
 Chiral Dinuclear Vanadium Complex-Mediated Oxidative Coupling of
 Resorcinols.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1580
_journal_page_last               1587
_journal_paper_doi               10.1021/acs.joc.8b02494
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C24 H18 O4'
_chemical_formula_sum            'C24 H18 O4'
_chemical_formula_weight         370.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.2833(2)
_cell_length_b                   12.8375(3)
_cell_length_c                   12.4934(9)
_cell_measurement_reflns_used    5502
_cell_measurement_temperature    123
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.44
_cell_volume                     1168.12(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2017/1 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID 191R'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            23058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_min         3.538
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             388.00
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.091
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0567P)²+0.9654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2058
_reflns_number_total             2151
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            jo8b02494_si_001.cif
_cod_data_source_block           No1_1_1
_cod_database_code               4036035
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,+Z
3 1/2+X,1/2-Y,-Z
4 1/2-X,1/2+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
O1 O 0.2752(4) 0.4651(2) 0.4485(2) 0.0492(8) Uani 1 1 d . .
H1 H 0.366985 0.425737 0.452884 0.059 Uiso 1 1 calc R U
O2 O 0.0380(4) 0.7779(2) 0.5852(3) 0.0530(8) Uani 1 1 d . .
H2 H 0.028863 0.807145 0.645098 0.064 Uiso 1 1 calc R U
C3 C 0.2906(5) 0.5435(3) 0.5222(3) 0.0391(9) Uani 1 1 d . .
C4 C 0.4307(5) 0.5441(3) 0.5992(3) 0.0345(8) Uani 1 1 d . .
C5 C 0.4348(5) 0.6250(3) 0.6731(3) 0.0382(9) Uani 1 1 d . .
C6 C 0.5742(6) 0.6302(3) 0.7604(3) 0.0438(10) Uani 1 1 d . .
C7 C 0.1674(6) 0.7006(3) 0.5908(4) 0.0439(10) Uani 1 1 d . .
C8 C 0.1592(6) 0.6199(3) 0.5163(4) 0.0453(10) Uani 1 1 d . .
H8 H 0.065894 0.617912 0.463216 0.054 Uiso 1 1 calc R U
C9 C 0.3018(6) 0.7050(3) 0.6690(4) 0.0457(10) Uani 1 1 d . .
H9 H 0.304468 0.760654 0.719077 0.055 Uiso 1 1 calc R U
C10 C 0.7625(6) 0.6200(3) 0.7408(4) 0.0457(10) Uani 1 1 d . .
H10 H 0.804145 0.610517 0.669366 0.055 Uiso 1 1 calc R U
C11 C 0.5181(8) 0.6446(4) 0.8667(4) 0.0537(12) Uani 1 1 d . .
H11 H 0.391011 0.651725 0.882196 0.064 Uiso 1 1 calc R U
C12 C 0.8310(8) 0.6377(4) 0.9274(4) 0.0632(14) Uani 1 1 d . .
H12 H 0.918348 0.640056 0.983799 0.076 Uiso 1 1 calc R U
C13 C 0.8889(8) 0.6233(4) 0.8229(4) 0.0576(12) Uani 1 1 d . .
H13 H 1.015965 0.615699 0.807693 0.069 Uiso 1 1 calc R U
C14 C 0.6446(9) 0.6487(4) 0.9497(4) 0.0658(15) Uani 1 1 d . .
H14 H 0.604319 0.658925 1.021243 0.079 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(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_3
C3 O1 H1 109.5 .
C7 O2 H2 109.5 .
O1 C3 C8 115.6(4) .
O1 C3 C4 121.6(4) .
C8 C3 C4 122.7(4) .
C5 C4 C3 118.3(4) .
C5 C4 C4 122.9(3) 2_665
C3 C4 C4 118.7(3) 2_665
C4 C5 C9 120.3(4) .
C4 C5 C6 122.2(4) .
C9 C5 C6 117.4(4) .
C10 C6 C11 117.7(4) .
C10 C6 C5 122.3(4) .
C11 C6 C5 120.0(4) .
O2 C7 C9 119.6(4) .
O2 C7 C8 118.3(4) .
C9 C7 C8 122.1(4) .
C3 C8 C7 117.8(4) .
C3 C8 H8 121.1 .
C7 C8 H8 121.1 .
C7 C9 C5 118.8(4) .
C7 C9 H9 120.6 .
C5 C9 H9 120.6 .
C13 C10 C6 121.4(4) .
C13 C10 H10 119.3 .
C6 C10 H10 119.3 .
C14 C11 C6 121.3(5) .
C14 C11 H11 119.4 .
C6 C11 H11 119.4 .
C13 C12 C14 119.9(5) .
C13 C12 H12 120.0 .
C14 C12 H12 120.0 .
C12 C13 C10 120.2(5) .
C12 C13 H13 119.9 .
C10 C13 H13 119.9 .
C11 C14 C12 119.6(5) .
C11 C14 H14 120.2 .
C12 C14 H14 120.2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.369(5) .
O1 H1 0.8400 .
O2 C7 1.370(5) .
O2 H2 0.8400 .
C3 C8 1.372(6) .
C3 C4 1.402(5) .
C4 C5 1.391(6) .
C4 C4 1.516(8) 2_665
C5 C9 1.412(6) .
C5 C6 1.492(6) .
C6 C10 1.399(6) .
C6 C11 1.402(6) .
C7 C9 1.385(6) .
C7 C8 1.394(6) .
C8 H8 0.9500 .
C9 H9 0.9500 .
C10 C13 1.379(6) .
C10 H10 0.9500 .
C11 C14 1.388(7) .
C11 H11 0.9500 .
C12 C13 1.384(7) .
C12 C14 1.393(8) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O2 4_546 2.794(4) 0.840 2.076 143.2 no
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_4
O1 C3 C4 C5 -178.4(4) . .
C8 C3 C4 C5 0.7(6) . .
O1 C3 C4 C4 0.8(6) . 2_665
C8 C3 C4 C4 179.9(4) . 2_665
C3 C4 C5 C9 -0.8(6) . .
C4 C4 C5 C9 -180.0(4) 2_665 .
C3 C4 C5 C6 177.7(4) . .
C4 C4 C5 C6 -1.5(6) 2_665 .
C4 C5 C6 C10 50.9(6) . .
C9 C5 C6 C10 -130.6(4) . .
C4 C5 C6 C11 -128.4(5) . .
C9 C5 C6 C11 50.2(6) . .
O1 C3 C8 C7 179.0(4) . .
C4 C3 C8 C7 -0.2(6) . .
O2 C7 C8 C3 179.5(4) . .
C9 C7 C8 C3 -0.2(6) . .
O2 C7 C9 C5 -179.6(4) . .
C8 C7 C9 C5 0.1(6) . .
C4 C5 C9 C7 0.4(6) . .
C6 C5 C9 C7 -178.2(4) . .
C11 C6 C10 C13 0.3(7) . .
C5 C6 C10 C13 -178.9(4) . .
C10 C6 C11 C14 0.1(7) . .
C5 C6 C11 C14 179.3(4) . .
C14 C12 C13 C10 0.1(8) . .
C6 C10 C13 C12 -0.4(7) . .
C6 C11 C14 C12 -0.4(8) . .
C13 C12 C14 C11 0.3(9) . .
