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#$Date: 2020-07-23 04:05:25 +0300 (Thu, 23 Jul 2020) $
#$Revision: 254490 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/86/1558659.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_1558659
loop_
_publ_author_name
'Yuan, Yuan'
'Zhang, Xue'
'Qian, Hui'
'Ma, Shengming'
_publ_section_title
;
 Catalytic enantioselective allene-anhydride approach to β,γ-unsaturated
 enones bearing an α-all-carbon-quaternary center
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03227A
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C23 H20 O'
_chemical_formula_weight         312.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-11 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.3690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8749(4)
_cell_length_b                   6.1545(2)
_cell_length_c                   12.1392(4)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      140.282
_cell_measurement_theta_min      7.553
_cell_volume                     855.46(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11285
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.384
_diffrn_reflns_theta_min         3.776
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_extinction_coef       0.069(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0389
_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)+(0.0733P)²+0.0304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1109
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2937
_reflns_number_total             3022
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03227a3.cif
_cod_data_source_block           cu_d8v19418_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558659
_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_min   0.897
_shelx_estimated_absorpt_t_max   0.931
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23583(15) 0.1839(3) 0.07775(15) 0.0624(5) Uani 1 1 d . . . . .
C1 C 0.28711(18) 0.3264(3) 0.13989(17) 0.0459(5) Uani 1 1 d . . . . .
C2 C 0.21844(17) 0.4797(3) 0.19948(17) 0.0442(5) Uani 1 1 d . . . . .
C3 C 0.21071(17) 0.6919(3) 0.13343(18) 0.0461(5) Uani 1 1 d . . . . .
H3 H 0.2387 0.8204 0.1751 0.055 Uiso 1 1 calc R U . . .
C4 C 0.1675(2) 0.7082(4) 0.0218(2) 0.0535(5) Uani 1 1 d . . . . .
C5 C 0.09404(18) 0.3798(4) 0.18408(18) 0.0488(5) Uani 1 1 d . . . . .
H5A H 0.0544 0.3720 0.1014 0.059 Uiso 1 1 calc R U . . .
H5B H 0.1027 0.2294 0.2140 0.059 Uiso 1 1 calc R U . . .
C6 C 0.01731(17) 0.5049(4) 0.24299(18) 0.0494(5) Uani 1 1 d . . . . .
C7 C -0.03776(19) 0.6962(5) 0.1982(2) 0.0581(6) Uani 1 1 d . . . . .
H7 H -0.0308 0.7473 0.1265 0.070 Uiso 1 1 calc R U . . .
C8 C -0.1031(2) 0.8144(5) 0.2570(2) 0.0671(7) Uani 1 1 d . . . . .
H8 H -0.1387 0.9473 0.2264 0.080 Uiso 1 1 calc R U . . .
C9 C -0.1163(2) 0.7385(5) 0.3599(2) 0.0672(7) Uani 1 1 d . . . . .
H9 H -0.1607 0.8194 0.4003 0.081 Uiso 1 1 calc R U . . .
C10 C -0.0655(2) 0.5469(6) 0.4035(2) 0.0671(7) Uani 1 1 d . . . . .
H10 H -0.0762 0.4924 0.4732 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0020(2) 0.4311(5) 0.3456(2) 0.0601(6) Uani 1 1 d . . . . .
H11 H 0.0381 0.2993 0.3772 0.072 Uiso 1 1 calc R U . . .
C12 C 0.27713(17) 0.5034(3) 0.32766(17) 0.0442(5) Uani 1 1 d . . . . .
C13 C 0.26484(19) 0.6903(4) 0.3871(2) 0.0521(5) Uani 1 1 d . . . . .
H13 H 0.2224 0.8103 0.3474 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3141(2) 0.7038(5) 0.5045(2) 0.0595(6) Uani 1 1 d . . . . .
H14 H 0.3055 0.8330 0.5443 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3758(2) 0.5296(5) 0.56374(19) 0.0600(6) Uani 1 1 d . . . . .
H15 H 0.4100 0.5394 0.6437 0.072 Uiso 1 1 calc R U . . .
C16 C 0.3869(2) 0.3423(5) 0.50548(19) 0.0585(6) Uani 1 1 d . . . . .
H16 H 0.4287 0.2221 0.5456 0.070 Uiso 1 1 calc R U . . .
C17 C 0.33762(19) 0.3279(4) 0.38862(19) 0.0512(5) Uani 1 1 d . . . . .
H17 H 0.3451 0.1970 0.3496 0.061 Uiso 1 1 calc R U . . .
C18 C 0.41562(19) 0.3574(4) 0.15331(17) 0.0460(5) Uani 1 1 d . . . . .
C19 C 0.47766(18) 0.5401(4) 0.20332(18) 0.0516(5) Uani 1 1 d . . . . .
H19 H 0.4387 0.6529 0.2319 0.062 Uiso 1 1 calc R U . . .
C20 C 0.5964(2) 0.5584(5) 0.2117(2) 0.0592(6) Uani 1 1 d . . . . .
H20 H 0.6382 0.6838 0.2455 0.071 Uiso 1 1 calc R U . . .
C21 C 0.6537(2) 0.3934(5) 0.1706(2) 0.0640(7) Uani 1 1 d . . . . .
H21 H 0.7350 0.4051 0.1768 0.077 Uiso 1 1 calc R U . . .
C22 C 0.5924(2) 0.2117(5) 0.1206(2) 0.0643(7) Uani 1 1 d . . . . .
H22 H 0.6317 0.0988 0.0923 0.077 Uiso 1 1 calc R U . . .
C23 C 0.4740(2) 0.1938(4) 0.11160(18) 0.0552(6) Uani 1 1 d . . . . .
H23 H 0.4324 0.0690 0.0767 0.066 Uiso 1 1 calc R U . . .
H4A H 0.172(2) 0.849(5) -0.019(2) 0.055(7) Uiso 1 1 d . . . . .
H4B H 0.137(3) 0.582(6) -0.025(3) 0.072(9) Uiso 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 0.0181 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_
_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
O1 C1 C18 119.23(19) . . ?
O1 C1 C2 119.54(19) . . ?
C18 C1 C2 121.17(17) . . ?
C3 C2 C12 113.60(16) . . ?
C3 C2 C1 104.05(16) . . ?
C12 C2 C1 112.24(16) . . ?
C3 C2 C5 110.54(16) . . ?
C12 C2 C5 108.62(16) . . ?
C1 C2 C5 107.60(16) . . ?
C4 C3 C2 124.0(2) . . ?
C4 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
C3 C4 H4A 120.7(16) . . ?
C3 C4 H4B 121.3(19) . . ?
H4A C4 H4B 118(2) . . ?
C6 C5 C2 114.33(17) . . ?
C6 C5 H5A 108.7 . . ?
C2 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C2 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C11 C6 C7 118.1(2) . . ?
C11 C6 C5 119.9(2) . . ?
C7 C6 C5 121.9(2) . . ?
C6 C7 C8 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.0(3) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C6 C11 C10 121.1(3) . . ?
C6 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C17 118.48(19) . . ?
C13 C12 C2 121.65(18) . . ?
C17 C12 C2 119.71(18) . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.4(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.7(2) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C23 C18 C19 119.1(2) . . ?
C23 C18 C1 117.23(19) . . ?
C19 C18 C1 123.69(19) . . ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C18 120.4(2) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
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 1.211(3) . ?
C1 C18 1.503(3) . ?
C1 C2 1.546(3) . ?
C2 C3 1.522(3) . ?
C2 C12 1.534(3) . ?
C2 C5 1.565(3) . ?
C3 C4 1.320(3) . ?
C3 H3 0.9500 . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.98(3) . ?
C5 C6 1.510(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.382(3) . ?
C6 C7 1.386(4) . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C12 C17 1.396(3) . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.392(3) . ?
C18 C19 1.392(3) . ?
C19 C20 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
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
_geom_torsion_publ_flag
O1 C1 C2 C3 -105.3(2) . . . . ?
C18 C1 C2 C3 71.7(2) . . . . ?
O1 C1 C2 C12 131.4(2) . . . . ?
C18 C1 C2 C12 -51.5(2) . . . . ?
O1 C1 C2 C5 12.0(3) . . . . ?
C18 C1 C2 C5 -170.93(17) . . . . ?
C12 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C4 55.1(3) . . . . ?
C5 C2 C3 C4 -60.1(3) . . . . ?
C3 C2 C5 C6 -70.0(2) . . . . ?
C12 C2 C5 C6 55.3(2) . . . . ?
C1 C2 C5 C6 177.03(17) . . . . ?
C2 C5 C6 C11 -101.8(2) . . . . ?
C2 C5 C6 C7 77.1(3) . . . . ?
C11 C6 C7 C8 2.2(3) . . . . ?
C5 C6 C7 C8 -176.7(2) . . . . ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C7 C6 C11 C10 -0.9(4) . . . . ?
C5 C6 C11 C10 178.1(2) . . . . ?
C9 C10 C11 C6 -1.1(4) . . . . ?
C3 C2 C12 C13 33.8(3) . . . . ?
C1 C2 C12 C13 151.5(2) . . . . ?
C5 C2 C12 C13 -89.6(2) . . . . ?
C3 C2 C12 C17 -150.9(2) . . . . ?
C1 C2 C12 C17 -33.2(3) . . . . ?
C5 C2 C12 C17 85.7(2) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
C2 C12 C13 C14 176.8(2) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C12 0.8(3) . . . . ?
C13 C12 C17 C16 -1.7(3) . . . . ?
C2 C12 C17 C16 -177.12(19) . . . . ?
O1 C1 C18 C23 -12.5(3) . . . . ?
C2 C1 C18 C23 170.38(19) . . . . ?
O1 C1 C18 C19 166.7(2) . . . . ?
C2 C1 C18 C19 -10.4(3) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C1 C18 C19 C20 -179.3(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -0.4(4) . . . . ?
C19 C18 C23 C22 0.5(3) . . . . ?
C1 C18 C23 C22 179.8(2) . . . . ?
