#------------------------------------------------------------------------------
#$Date: 2022-12-10 04:02:39 +0200 (Sat, 10 Dec 2022) $
#$Revision: 279830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245993.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_7245993
loop_
_publ_author_name
'Tong, Zhou'
'Peng, Xinju'
'Tang, Zhi'
'Yang, Weijun'
'Deng, Wei'
'Yin, Shuang-Feng'
'Kambe, Nobuaki'
'Qiu, Renhua'
_publ_section_title
;
 DTBP-mediated cross-dehydrogenative coupling of 3-aryl
 benzofuran-2(3H)-ones with toluenes/phenols for all-carbon quaternary
 centers
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              35215
_journal_page_last               35220
_journal_paper_doi               10.1039/D2RA06231C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-27 deposited with the CCDC.	2022-12-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.571(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6597(9)
_cell_length_b                   9.1073(4)
_cell_length_c                   10.5974(6)
_cell_measurement_reflns_used    3745
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      29.1210
_cell_measurement_theta_min      2.4330
_cell_volume                     1602.78(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -33.00  58.00   1.00    2.50    --  -11.43  57.00  30.00   91
  2  ω    -74.00  17.00   1.00    2.50    --  -11.43 -77.00 120.00   91
  3  ω    -81.00  17.00   1.00    2.50    --  -11.43 -57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0322620000
_diffrn_orient_matrix_UB_12      -0.0435437000
_diffrn_orient_matrix_UB_13      -0.0189436000
_diffrn_orient_matrix_UB_21      0.0012552000
_diffrn_orient_matrix_UB_22      0.0429513000
_diffrn_orient_matrix_UB_23      -0.0555772000
_diffrn_orient_matrix_UB_31      0.0279459000
_diffrn_orient_matrix_UB_32      0.0483326000
_diffrn_orient_matrix_UB_33      0.0324650000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5926
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.646
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.301
_diffrn_reflns_theta_min         2.453
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 846 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0322
_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)+(0.0376P)²+0.4721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.464
_reflns_Friedel_fraction_full    0.554
_reflns_Friedel_fraction_max     0.410
_reflns_number_gt                2758
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra06231c2.cif
_cod_data_source_block           tz-1
_cod_database_code               7245993
_shelx_shelxl_version_number     2018/3
_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 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C19(H19), C17(H17), C4(H4), C2(H2), C3(H3), C5(H5),
 C12(H12), C13(H13), C20(H20), C14(H14), C11(H11)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.402
_oxdiff_exptl_absorpt_empirical_full_min 0.764
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 0.56412(8) 0.70472(14) 0.72693(13) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.67625(9) 0.60928(15) 0.65704(14) 0.0258(3) Uani 1 1 d . . . . .
C15 C 0.61204(11) 0.66641(19) 0.63210(19) 0.0181(4) Uani 1 1 d . . . . .
C21 C 0.49381(11) 0.76964(19) 0.67049(19) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.62462(12) 0.9600(2) 0.4645(2) 0.0207(4) Uani 1 1 d . . . . .
H10 H 0.596210 0.991210 0.531613 0.025 Uiso 1 1 calc R . . . .
C6 C 0.52877(12) 0.3374(2) 0.56535(19) 0.0199(4) Uani 1 1 d . . . . .
H6 H 0.584301 0.325415 0.576989 0.024 Uiso 1 1 calc R . . . .
C19 C 0.36486(12) 0.87668(19) 0.6631(2) 0.0198(4) Uani 1 1 d . . . . .
H19 H 0.321098 0.910774 0.703872 0.024 Uiso 1 1 calc R . . . .
C1 C 0.49669(12) 0.45316(19) 0.49014(19) 0.0180(4) Uani 1 1 d . . . . .
C16 C 0.49367(11) 0.77559(19) 0.54029(19) 0.0161(4) Uani 1 1 d . . . . .
C17 C 0.42783(11) 0.8344(2) 0.4690(2) 0.0174(4) Uani 1 1 d . . . . .
H17 H 0.427626 0.840631 0.381385 0.021 Uiso 1 1 calc R . . . .
C4 C 0.39551(12) 0.2582(2) 0.6076(2) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.361930 0.194633 0.647481 0.026 Uiso 1 1 calc R . . . .
C9 C 0.62217(11) 0.8114(2) 0.42925(19) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.41308(12) 0.4676(2) 0.4734(2) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.390726 0.542208 0.422021 0.024 Uiso 1 1 calc R . . . .
C3 C 0.36269(12) 0.3721(2) 0.5323(2) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.307144 0.384168 0.521386 0.027 Uiso 1 1 calc R . . . .
C5 C 0.47841(12) 0.2400(2) 0.6230(2) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.500394 0.162739 0.671658 0.026 Uiso 1 1 calc R . . . .
C12 C 0.71134(12) 1.0159(2) 0.3001(2) 0.0235(4) Uani 1 1 d . . . . .
H12 H 0.740311 1.083621 0.256241 0.028 Uiso 1 1 calc R . . . .
C13 C 0.71039(12) 0.8689(2) 0.2653(2) 0.0233(4) Uani 1 1 d . . . . .
H13 H 0.739295 0.838182 0.198607 0.028 Uiso 1 1 calc R . . . .
C20 C 0.43112(12) 0.8200(2) 0.7360(2) 0.0203(4) Uani 1 1 d . . . . .
H20 H 0.432896 0.816471 0.823876 0.024 Uiso 1 1 calc R . . . .
C18 C 0.36178(11) 0.88414(19) 0.5308(2) 0.0179(4) Uani 1 1 d . . . . .
C7 C 0.55168(12) 0.55876(19) 0.42679(19) 0.0175(4) Uani 1 1 d . . . . .
H7A H 0.527077 0.582600 0.343263 0.021 Uiso 1 1 calc R . . . .
H7B H 0.602217 0.509312 0.415760 0.021 Uiso 1 1 calc R . . . .
C14 C 0.66634(11) 0.7670(2) 0.32989(19) 0.0192(4) Uani 1 1 d . . . . .
H14 H 0.666502 0.668666 0.306301 0.023 Uiso 1 1 calc R . . . .
C11 C 0.66894(13) 1.0614(2) 0.4004(2) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.670081 1.159454 0.424887 0.030 Uiso 1 1 calc R . . . .
C8 C 0.57006(11) 0.70491(19) 0.50074(19) 0.0162(4) Uani 1 1 d . . . . .
C22 C 0.28860(12) 0.9453(2) 0.4551(2) 0.0235(4) Uani 1 1 d . . . . .
H22A H 0.241825 0.930613 0.500967 0.035 Uiso 1 1 calc GR . . . .
H22B H 0.281458 0.895654 0.375076 0.035 Uiso 1 1 calc GR . . . .
H22C H 0.296027 1.048372 0.441221 0.035 Uiso 1 1 calc GR . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C21 107.96(15) . . ?
O1 C15 C8 110.63(15) . . ?
O2 C15 O1 120.49(18) . . ?
O2 C15 C8 128.86(18) . . ?
C16 C21 O1 112.18(16) . . ?
C20 C21 O1 124.48(18) . . ?
C20 C21 C16 123.33(18) . . ?
C11 C10 C9 121.00(19) . . ?
C5 C6 C1 120.80(18) . . ?
C20 C19 C18 122.45(18) . . ?
C6 C1 C7 120.72(17) . . ?
C2 C1 C6 118.31(18) . . ?
C2 C1 C7 120.96(17) . . ?
C21 C16 C17 119.81(17) . . ?
C21 C16 C8 108.98(16) . . ?
C17 C16 C8 131.14(19) . . ?
C16 C17 C18 119.12(19) . . ?
C5 C4 C3 119.86(18) . . ?
C10 C9 C8 118.80(17) . . ?
C14 C9 C10 118.36(18) . . ?
C14 C9 C8 122.83(16) . . ?
C3 C2 C1 121.06(18) . . ?
C2 C3 C4 119.94(19) . . ?
C4 C5 C6 120.00(18) . . ?
C11 C12 C13 119.73(19) . . ?
C12 C13 C14 120.4(2) . . ?
C21 C20 C19 116.25(19) . . ?
C19 C18 C22 120.84(17) . . ?
C17 C18 C19 119.01(17) . . ?
C17 C18 C22 120.14(18) . . ?
C1 C7 C8 114.72(16) . . ?
C9 C14 C13 120.54(18) . . ?
C12 C11 C10 119.91(19) . . ?
C15 C8 C7 108.34(14) . . ?
C16 C8 C15 100.18(16) . . ?
C16 C8 C9 112.80(14) . . ?
C16 C8 C7 111.43(15) . . ?
C9 C8 C15 110.68(15) . . ?
C9 C8 C7 112.65(16) . . ?
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 C15 1.377(2) . ?
O1 C21 1.403(2) . ?
O2 C15 1.200(2) . ?
C15 C8 1.547(3) . ?
C21 C16 1.381(3) . ?
C21 C20 1.378(3) . ?
C10 C9 1.404(3) . ?
C10 C11 1.392(3) . ?
C6 C1 1.402(3) . ?
C6 C5 1.395(3) . ?
C19 C20 1.395(3) . ?
C19 C18 1.401(3) . ?
C1 C2 1.396(3) . ?
C1 C7 1.521(3) . ?
C16 C17 1.389(3) . ?
C16 C8 1.515(3) . ?
C17 C18 1.400(3) . ?
C4 C3 1.393(3) . ?
C4 C5 1.388(3) . ?
C9 C14 1.392(3) . ?
C9 C8 1.540(3) . ?
C2 C3 1.391(3) . ?
C12 C13 1.388(3) . ?
C12 C11 1.385(3) . ?
C13 C14 1.396(3) . ?
C18 C22 1.511(3) . ?
C7 C8 1.562(3) . ?
