#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:34:55 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257389 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557750.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_1557750
loop_
_publ_author_name
'Baek, Doohyun'
'Ryu, Huijeong'
'Ryu, Ji Yeon'
'Lee, Junseong'
'Stoltz, Brian M.'
'Hong, Sukwon'
_publ_section_title
;
 Catalytic enantioselective synthesis of tetrasubstituted chromanones via
 palladium-catalyzed asymmetric conjugate arylation using chiral
 pyridine-dihydroisoquinoline ligands
;
_journal_issue                   18
_journal_name_full               'Chemical Science'
_journal_page_first              4602
_journal_page_last               4607
_journal_paper_doi               10.1039/D0SC00412J
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C20 H22 O2'
_chemical_formula_sum            'C20 H22 O2'
_chemical_formula_weight         294.37
_chemical_name_systematic
(S)-2-(4-(tert-butyl)phenyl)-2-methylchroman-4-one
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-09-20 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.9349(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.2747(4)
_cell_length_b                   6.77810(10)
_cell_length_c                   10.2443(2)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.61
_cell_volume                     1615.20(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12536
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.424
_diffrn_reflns_theta_min         1.751
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0306
_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)+(0.0501P)²+0.4895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2880
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc00412j2.cif
_cod_data_source_block           hsw58-1
_cod_depositor_comments
;Adding full bibliography for 1557749--1557750.cif.

 Adding full bibliography for 1557749--1557750.cif.
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               1557750
_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   0.985
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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 0.82315(7) 1.0358(2) 0.40751(14) 0.0409(4) Uani 1 1 d . . . . .
O2 O 0.84674(5) 0.77465(19) 0.05311(11) 0.0247(3) Uani 1 1 d . . . . .
C1 C 0.82765(8) 0.9618(3) 0.30018(18) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.80026(7) 0.7732(3) 0.26200(16) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.80983(7) 0.6927(3) 0.13882(16) 0.0214(4) Uani 1 1 d . . . . .
C4 C 0.88971(7) 0.9109(3) 0.10712(17) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.85963(8) 1.0606(3) 0.19274(19) 0.0281(4) Uani 1 1 d . . . . .
H5A H 0.8880 1.1503 0.2310 0.034 Uiso 1 1 calc R U . . .
H5B H 0.8328 1.1375 0.1390 0.034 Uiso 1 1 calc R U . . .
C6 C 0.76189(7) 0.6776(3) 0.34329(17) 0.0274(4) Uani 1 1 d . . . . .
H6 H 0.7557 0.7283 0.4260 0.033 Uiso 1 1 calc R U . . .
C7 C 0.73324(7) 0.5096(3) 0.30269(18) 0.0297(4) Uani 1 1 d . . . . .
H7 H 0.7080 0.4469 0.3576 0.036 Uiso 1 1 calc R U . . .
C8 C 0.74244(8) 0.4343(3) 0.17859(19) 0.0299(4) Uani 1 1 d . . . . .
H8 H 0.7228 0.3217 0.1505 0.036 Uiso 1 1 calc R U . . .
C9 C 0.78048(7) 0.5249(3) 0.09642(17) 0.0270(4) Uani 1 1 d . . . . .
H9 H 0.7863 0.4738 0.0136 0.032 Uiso 1 1 calc R U . . .
C10 C 0.91402(8) 1.0090(3) -0.01302(19) 0.0352(5) Uani 1 1 d . . . . .
H10A H 0.8837 1.0750 -0.0614 0.053 Uiso 1 1 calc R U . . .
H10B H 0.9309 0.9105 -0.0672 0.053 Uiso 1 1 calc R U . . .
H10C H 0.9429 1.1032 0.0139 0.053 Uiso 1 1 calc R U . . .
C11 C 0.93697(7) 0.7938(3) 0.17985(16) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.95035(8) 0.6038(3) 0.1407(2) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.9277 0.5427 0.0760 0.040 Uiso 1 1 calc R U . . .
C13 C 0.99698(8) 0.5037(3) 0.1968(2) 0.0344(4) Uani 1 1 d . . . . .
H13 H 1.0049 0.3766 0.1684 0.041 Uiso 1 1 calc R U . . .
C14 C 1.03217(7) 0.5875(3) 0.29412(16) 0.0228(4) Uani 1 1 d . . . . .
C15 C 1.01794(8) 0.7764(3) 0.33375(17) 0.0259(4) Uani 1 1 d . . . . .
H15 H 1.0402 0.8372 0.3992 0.031 Uiso 1 1 calc R U . . .
C16 C 0.97125(8) 0.8774(3) 0.27826(18) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.9629 1.0035 0.3078 0.032 Uiso 1 1 calc R U . . .
C17 C 1.08623(7) 0.4803(3) 0.34771(18) 0.0262(4) Uani 1 1 d . . . . .
C18 C 1.13274(9) 0.5026(4) 0.2458(3) 0.0473(6) Uani 1 1 d . . . . .
H18A H 1.1674 0.4385 0.2768 0.071 Uiso 1 1 calc R U . . .
H18B H 1.1403 0.6401 0.2318 0.071 Uiso 1 1 calc R U . . .
H18C H 1.1196 0.4432 0.1651 0.071 Uiso 1 1 calc R U . . .
C19 C 1.07472(9) 0.2601(3) 0.3667(2) 0.0373(5) Uani 1 1 d . . . . .
H19A H 1.0448 0.2433 0.4279 0.056 Uiso 1 1 calc R U . . .
H19B H 1.1091 0.1968 0.3997 0.056 Uiso 1 1 calc R U . . .
H19C H 1.0630 0.2021 0.2845 0.056 Uiso 1 1 calc R U . . .
C20 C 1.10830(10) 0.5654(4) 0.4771(2) 0.0509(7) Uani 1 1 d . . . . .
H20A H 1.1211 0.6984 0.4642 0.076 Uiso 1 1 calc R U . . .
H20B H 1.1398 0.4869 0.5107 0.076 Uiso 1 1 calc R U . . .
H20C H 1.0779 0.5647 0.5383 0.076 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 0.0033 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
C3 O2 C4 116.87(12) . . ?
O1 C1 C2 123.18(18) . . ?
O1 C1 C5 122.50(18) . . ?
C2 C1 C5 114.26(16) . . ?
C3 C2 C6 118.66(17) . . ?
C3 C2 C1 119.77(16) . . ?
C6 C2 C1 121.46(16) . . ?
O2 C3 C9 116.42(15) . . ?
O2 C3 C2 122.90(16) . . ?
C9 C3 C2 120.66(16) . . ?
O2 C4 C10 103.81(14) . . ?
O2 C4 C5 108.49(13) . . ?
C10 C4 C5 111.36(16) . . ?
O2 C4 C11 109.21(14) . . ?
C10 C4 C11 109.83(14) . . ?
C5 C4 C11 113.65(14) . . ?
C1 C5 C4 111.86(16) . . ?
C7 C6 C2 121.02(17) . . ?
C6 C7 C8 119.38(17) . . ?
C9 C8 C7 120.88(18) . . ?
C8 C9 C3 119.38(16) . . ?
C16 C11 C12 117.40(16) . . ?
C16 C11 C4 121.96(16) . . ?
C12 C11 C4 120.39(16) . . ?
C11 C12 C13 120.96(18) . . ?
C12 C13 C14 122.04(19) . . ?
C15 C14 C13 116.52(17) . . ?
C15 C14 C17 122.14(15) . . ?
C13 C14 C17 121.21(17) . . ?
C14 C15 C16 121.74(16) . . ?
C11 C16 C15 121.31(17) . . ?
C20 C17 C19 108.34(18) . . ?
C20 C17 C18 109.30(18) . . ?
C19 C17 C18 108.22(17) . . ?
C20 C17 C14 112.37(16) . . ?
C19 C17 C14 111.19(15) . . ?
C18 C17 C14 107.32(15) . . ?
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 1.216(2) . ?
O2 C3 1.367(2) . ?
O2 C4 1.457(2) . ?
C1 C2 1.475(3) . ?
C1 C5 1.506(3) . ?
C2 C3 1.400(2) . ?
C2 C6 1.401(3) . ?
C3 C9 1.389(3) . ?
C4 C10 1.524(2) . ?
C4 C5 1.526(3) . ?
C4 C11 1.530(2) . ?
C6 C7 1.377(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.386(3) . ?
C11 C16 1.386(2) . ?
C11 C12 1.387(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.387(3) . ?
C14 C17 1.538(2) . ?
C15 C16 1.389(3) . ?
C17 C20 1.519(3) . ?
C17 C19 1.530(3) . ?
C17 C18 1.537(3) . ?
