#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:07:04 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254920 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/67/7126766.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_7126766
loop_
_publ_author_name
'Niu, Jia-Pan'
'Nie, Jing'
'Li, Shen'
'Ma, Jun-An'
_publ_section_title
;
 Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot
 tandem dehydration/1,6-addition/decarboxylation transformation of β-keto
 acids and 4-hydroxybenzyl alcohols.
;
_journal_issue                   61
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8687
_journal_page_last               8690
_journal_paper_doi               10.1039/d0cc02213f
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H14 O3'
_chemical_formula_sum            'C15 H14 O3'
_chemical_formula_weight         242.26
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc25fv1j
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-06-11 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8696(4)
_cell_length_b                   10.0626(8)
_cell_length_c                   20.1420(16)
_cell_measurement_reflns_used    9317
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.672
_cell_measurement_theta_min      4.390
_cell_volume                     1189.66(16)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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_temperature      170
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16116
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.833
_diffrn_reflns_theta_min         4.390
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1657 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7604. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 901 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0340P)²+0.3622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2302
_reflns_number_total             2447
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02213f2.cif
_cod_data_source_block           0608648c_0m
_cod_depositor_comments
'Adding full bibliography for 7126766--7126768.cif.'
_cod_database_code               7126766
_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.
;
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.894
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C12(H12), C1(H1A), C3(H3), C11(H11), C5(H5), C2(H2A),
 C4(H4)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.4623(3) 1.02478(17) 0.53100(9) 0.0333(4) Uani 1 1 d . . . . .
H1 H 0.599168 1.044170 0.523591 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.3939(3) 0.4013(2) 0.49796(8) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.6850(3) 0.4094(2) 0.56852(8) 0.0357(4) Uani 1 1 d . . . . .
H2 H 0.759004 0.422076 0.533392 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.4086(4) 0.6570(2) 0.62611(11) 0.0277(5) Uani 1 1 d . . . . .
C14 C 0.2533(4) 0.8285(2) 0.55459(11) 0.0307(5) Uani 1 1 d . . . . .
H14 H 0.132486 0.860879 0.527682 0.037 Uiso 1 1 calc R . . . .
C13 C 0.4509(4) 0.9018(2) 0.56201(11) 0.0284(5) Uani 1 1 d . . . . .
C15 C 0.2331(4) 0.7071(2) 0.58685(11) 0.0292(5) Uani 1 1 d . . . . .
H15 H 0.096723 0.657093 0.582034 0.035 Uiso 1 1 calc R . . . .
C6 C 0.2277(4) 0.5396(2) 0.72278(11) 0.0285(5) Uani 1 1 d . . . . .
C7 C 0.3864(4) 0.5251(2) 0.66268(11) 0.0284(5) Uani 1 1 d . . . . .
H7 H 0.540910 0.502383 0.680274 0.034 Uiso 1 1 calc R . . . .
C9 C 0.4646(4) 0.4068(2) 0.55485(12) 0.0291(5) Uani 1 1 d . . . . .
C8 C 0.3164(4) 0.4121(2) 0.61551(11) 0.0303(5) Uani 1 1 d . . . . .
H8A H 0.326553 0.326300 0.639361 0.036 Uiso 1 1 calc R . . . .
H8B H 0.155989 0.425101 0.601810 0.036 Uiso 1 1 calc R . . . .
C12 C 0.6281(4) 0.8544(3) 0.60029(12) 0.0315(5) Uani 1 1 d . . . . .
H12 H 0.763878 0.904866 0.605039 0.038 Uiso 1 1 calc R . . . .
C1 C 0.2879(4) 0.6296(2) 0.77225(12) 0.0350(5) Uani 1 1 d . . . . .
H1A H 0.424891 0.679248 0.768114 0.042 Uiso 1 1 calc R . . . .
C3 C -0.0504(5) 0.5776(3) 0.83415(12) 0.0361(6) Uani 1 1 d . . . . .
H3 H -0.145690 0.591407 0.871650 0.043 Uiso 1 1 calc R . . . .
C11 C 0.6065(4) 0.7321(2) 0.63186(12) 0.0309(5) Uani 1 1 d . . . . .
H11 H 0.729226 0.699317 0.657855 0.037 Uiso 1 1 calc R . . . .
C5 C 0.0275(4) 0.4684(3) 0.73043(12) 0.0353(6) Uani 1 1 d . . . . .
H5 H -0.016113 0.405755 0.697506 0.042 Uiso 1 1 calc R . . . .
C2 C 0.1505(5) 0.6478(3) 0.82742(13) 0.0393(6) Uani 1 1 d . . . . .
H2A H 0.194809 0.708982 0.860921 0.047 Uiso 1 1 calc R . . . .
C4 C -0.1109(4) 0.4876(3) 0.78594(12) 0.0385(6) Uani 1 1 d . . . . .
H4 H -0.247855 0.438063 0.790439 0.046 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_
_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
C13 O1 H1 109.5 . . ?
C9 O2 H2 109.5 . . ?
C15 C10 C7 121.7(2) . . ?
C11 C10 C15 117.9(2) . . ?
C11 C10 C7 120.3(2) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(2) . . ?
C15 C14 H14 120.3 . . ?
C14 C13 O1 117.9(2) . . ?
C12 C13 O1 121.6(2) . . ?
C12 C13 C14 120.5(2) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C7 123.6(2) . . ?
C5 C6 C1 118.2(2) . . ?
C10 C7 C6 110.49(19) . . ?
C10 C7 H7 107.0 . . ?
C10 C7 C8 111.61(18) . . ?
C6 C7 H7 107.0 . . ?
C6 C7 C8 113.32(18) . . ?
C8 C7 H7 107.0 . . ?
O3 C9 O2 122.0(2) . . ?
O3 C9 C8 124.7(2) . . ?
O2 C9 C8 113.4(2) . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 C7 112.02(19) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C6 C1 H1A 119.6 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C4 C3 C2 119.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.3(2) . . ?
C12 C11 H11 119.4 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C4 C5 H5 119.6 . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2A 119.7 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 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 H1 0.8400 . ?
O1 C13 1.388(3) . ?
O3 C9 1.220(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.323(3) . ?
C10 C15 1.393(3) . ?
C10 C7 1.524(3) . ?
C10 C11 1.391(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.383(3) . ?
C14 C15 1.389(3) . ?
C13 C12 1.380(3) . ?
C15 H15 0.9500 . ?
C6 C7 1.534(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.385(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.537(3) . ?
C9 C8 1.501(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C11 1.390(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(4) . ?
C3 C4 1.375(4) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.395(3) . ?
C2 H2A 0.9500 . ?
C4 H4 0.9500 . ?
