#------------------------------------------------------------------------------
#$Date: 2021-07-04 04:31:05 +0300 (Sun, 04 Jul 2021) $
#$Revision: 266955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/88/4518821.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_4518821
loop_
_publ_author_name
'Xu, Hao'
'Tan, Yun-Xuan'
'Xie, Pei-Pei'
'Ding, Rui'
'Liao, Qi'
'Zhang, Jian-Wei'
'Li, Qing-Hua'
'Wang, Yu-Hui'
'Hong, Xin'
'Lin, Guo-Qiang'
'Tian, Ping'
_publ_section_title
;
 Rhodium(III)-Catalyzed Asymmetric Reductive Cyclization of
 Cyclohexadienone-Containing 1,6-Dienes via an Anti-Michael/Michael
 Cascade Process
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              8015
_journal_page_last               8022
_journal_paper_doi               10.1021/acscatal.1c02431
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.27
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5908(6)
_cell_length_b                   12.4361(12)
_cell_length_c                   16.2473(15)
_cell_measurement_reflns_used    7032
_cell_measurement_temperature    237.(2)
_cell_measurement_theta_max      65.4333
_cell_measurement_theta_min      3.5541
_cell_volume                     1129.64(19)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      237.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'd8 venture'
_diffrn_radiation_type           'cu k\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8039
_diffrn_reflns_theta_full        65.59
_diffrn_reflns_theta_max         65.59
_diffrn_reflns_theta_min         4.48
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.156
_refine_ls_abs_structure_details
;

Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0295
_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)+(0.0337P)²+0.2104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                1901
_reflns_number_total             1938
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c02431_si_004.cif
_cod_data_source_block           2020050565A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4518820--4518825.cif.
;
_cod_database_code               4518821
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.4571(2) 0.59900(10) 0.59470(8) 0.0267(3) Uani d . . . 1 . .
O O2 0.9144(3) 0.42667(12) 0.81984(8) 0.0382(4) Uani d . . . 1 . .
O O3 0.5941(2) 0.38496(11) 0.63263(7) 0.0255(3) Uani d . . . 1 . .
H H18 0.521(5) 0.446(2) 0.6212(16) 0.049(8) Uiso d . . . 1 . .
C C1 0.8903(4) 0.20607(15) 0.58855(12) 0.0328(5) Uani d . . . 1 . .
H H3 0.71781 0.198483 0.590953 0.049 Uiso calc U . R 1 . .
H H4 0.965045 0.139642 0.606401 0.049 Uiso calc U . R 1 . .
H H1 0.938491 0.221822 0.532478 0.049 Uiso calc U . R 1 . .
C C2 0.9685(4) 0.29766(14) 0.64488(11) 0.0268(4) Uani d . . . 1 . .
H H17 0.933312 0.277937 0.702014 0.032 Uiso calc U . R 1 . .
H H16 1.141938 0.307046 0.640023 0.032 Uiso calc U . R 1 . .
C C3 0.8460(3) 0.40418(14) 0.62540(10) 0.0222(4) Uani d . . . 1 . .
C C4 0.9254(3) 0.49722(13) 0.68345(10) 0.0223(4) Uani d . . . 1 . .
H H12 1.101807 0.493949 0.688246 0.027 Uiso calc U . R 1 . .
C C5 0.8621(3) 0.60233(14) 0.63758(11) 0.0235(4) Uani d . . . 1 . .
H H13 0.987043 0.657384 0.64693 0.028 Uiso calc U . R 1 . .
C C6 0.6128(4) 0.64886(13) 0.65612(10) 0.0235(4) Uani d . . . 1 . .
C C7 0.5100(4) 0.61853(15) 0.73852(11) 0.0274(4) Uani d . . . 1 . .
H H2 0.368965 0.653175 0.755473 0.033 Uiso calc U . R 1 . .
C C8 0.9116(4) 0.45080(15) 0.54105(11) 0.0264(4) Uani d . . . 1 . .
H H5 0.819766 0.415216 0.497502 0.032 Uiso calc U . R 1 . .
H H6 1.082451 0.440662 0.529939 0.032 Uiso calc U . R 1 . .
C C9 0.8503(4) 0.57130(15) 0.54449(11) 0.0274(4) Uani d . . . 1 . .
H H15 0.966568 0.613874 0.512071 0.033 Uiso calc U . R 1 . .
C C10 0.5934(4) 0.59863(17) 0.51937(10) 0.0318(5) Uani d . . . 1 . .
H H8 0.586823 0.669289 0.492756 0.038 Uiso calc U . R 1 . .
H H7 0.530809 0.544613 0.481104 0.038 Uiso calc U . R 1 . .
C C11 0.6077(4) 0.77086(15) 0.64664(13) 0.0338(5) Uani d . . . 1 . .
H H11 0.686044 0.790891 0.595629 0.051 Uiso calc U . R 1 . .
H H10 0.690641 0.803801 0.692608 0.051 Uiso calc U . R 1 . .
H H9 0.443053 0.795463 0.645642 0.051 Uiso calc U . R 1 . .
C C12 0.6051(4) 0.54622(15) 0.78885(11) 0.0299(4) Uani d . . . 1 . .
H H14 0.52928 0.532988 0.839499 0.036 Uiso calc U . R 1 . .
C C13 0.8232(3) 0.48598(15) 0.76898(10) 0.0257(4) Uani d . . . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O1 C6 . . 105.43(14) ?
C3 O3 H18 . . 107.1(19) ?
C2 C1 H3 . . 109.5 ?
C2 C1 H4 . . 109.5 ?
H3 C1 H4 . . 109.5 ?
C2 C1 H1 . . 109.5 ?
H3 C1 H1 . . 109.5 ?
H4 C1 H1 . . 109.5 ?
C3 C2 C1 . . 113.32(16) ?
C3 C2 H17 . . 108.9 ?
C1 C2 H17 . . 108.9 ?
C3 C2 H16 . . 108.9 ?
C1 C2 H16 . . 108.9 ?
H17 C2 H16 . . 107.7 ?
O3 C3 C2 . . 106.22(15) ?
O3 C3 C8 . . 111.82(15) ?
C2 C3 C8 . . 114.02(15) ?
O3 C3 C4 . . 110.75(14) ?
C2 C3 C4 . . 113.07(15) ?
C8 C3 C4 . . 101.08(14) ?
C13 C4 C5 . . 115.82(15) ?
C13 C4 C3 . . 112.38(14) ?
C5 C4 C3 . . 105.72(14) ?
C13 C4 H12 . . 107.5 ?
C5 C4 H12 . . 107.5 ?
C3 C4 H12 . . 107.5 ?
C6 C5 C4 . . 115.54(15) ?
C6 C5 C9 . . 104.14(14) ?
C4 C5 C9 . . 105.52(14) ?
C6 C5 H13 . . 110.4 ?
C4 C5 H13 . . 110.4 ?
C9 C5 H13 . . 110.4 ?
O1 C6 C7 . . 105.88(15) ?
O1 C6 C11 . . 109.98(15) ?
C7 C6 C11 . . 109.39(15) ?
O1 C6 C5 . . 104.24(13) ?
C7 C6 C5 . . 115.20(15) ?
C11 C6 C5 . . 111.80(17) ?
C12 C7 C6 . . 124.44(17) ?
C12 C7 H2 . . 117.8 ?
C6 C7 H2 . . 117.8 ?
C3 C8 C9 . . 106.43(14) ?
C3 C8 H5 . . 110.4 ?
C9 C8 H5 . . 110.4 ?
C3 C8 H6 . . 110.4 ?
C9 C8 H6 . . 110.4 ?
H5 C8 H6 . . 108.6 ?
C10 C9 C8 . . 114.56(17) ?
C10 C9 C5 . . 104.04(15) ?
C8 C9 C5 . . 105.44(14) ?
C10 C9 H15 . . 110.8 ?
C8 C9 H15 . . 110.8 ?
C5 C9 H15 . . 110.8 ?
O1 C10 C9 . . 105.68(14) ?
O1 C10 H8 . . 110.6 ?
C9 C10 H8 . . 110.6 ?
O1 C10 H7 . . 110.6 ?
C9 C10 H7 . . 110.6 ?
H8 C10 H7 . . 108.7 ?
C6 C11 H11 . . 109.5 ?
C6 C11 H10 . . 109.5 ?
H11 C11 H10 . . 109.5 ?
C6 C11 H9 . . 109.5 ?
H11 C11 H9 . . 109.5 ?
H10 C11 H9 . . 109.5 ?
C7 C12 C13 . . 122.91(17) ?
C7 C12 H14 . . 118.5 ?
C13 C12 H14 . . 118.5 ?
O2 C13 C12 . . 120.48(17) ?
O2 C13 C4 . . 121.44(17) ?
C12 C13 C4 . . 118.05(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 . 1.442(2) ?
O1 C6 . 1.462(2) ?
O2 C13 . 1.219(2) ?
O3 C3 . 1.433(2) ?
O3 H18 . 0.88(3) ?
C1 C2 . 1.525(3) ?
C1 H3 . 0.97 ?
C1 H4 . 0.97 ?
C1 H1 . 0.97 ?
C2 C3 . 1.524(3) ?
C2 H17 . 0.98 ?
C2 H16 . 0.98 ?
C3 C8 . 1.533(2) ?
C3 C4 . 1.557(2) ?
C4 C13 . 1.509(2) ?
C4 C5 . 1.546(2) ?
C4 H12 . 0.99 ?
C5 C6 . 1.539(3) ?
C5 C9 . 1.562(2) ?
C5 H13 . 0.99 ?
C6 C7 . 1.505(3) ?
C6 C11 . 1.525(2) ?
C7 C12 . 1.326(3) ?
C7 H2 . 0.94 ?
C8 C9 . 1.538(3) ?
C8 H5 . 0.98 ?
C8 H6 . 0.98 ?
C9 C10 . 1.531(3) ?
C9 H15 . 0.99 ?
C10 H8 . 0.98 ?
C10 H7 . 0.98 ?
C11 H11 . 0.97 ?
C11 H10 . 0.97 ?
C11 H9 . 0.97 ?
C12 C13 . 1.467(3) ?
C12 H14 . 0.94 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 O3 . . . . 58.00(19) ?
C1 C2 C3 C8 . . . . -65.6(2) ?
C1 C2 C3 C4 . . . . 179.66(15) ?
O3 C3 C4 C13 . . . . 46.2(2) ?
C2 C3 C4 C13 . . . . -72.85(19) ?
C8 C3 C4 C13 . . . . 164.86(15) ?
O3 C3 C4 C5 . . . . -81.01(17) ?
C2 C3 C4 C5 . . . . 159.91(15) ?
C8 C3 C4 C5 . . . . 37.62(17) ?
C13 C4 C5 C6 . . . . -33.6(2) ?
C3 C4 C5 C6 . . . . 91.52(17) ?
C13 C4 C5 C9 . . . . -148.07(15) ?
C3 C4 C5 C9 . . . . -22.92(18) ?
C10 O1 C6 C7 . . . . -162.32(15) ?
C10 O1 C6 C11 . . . . 79.60(19) ?
C10 O1 C6 C5 . . . . -40.39(17) ?
C4 C5 C6 O1 . . . . -90.06(17) ?
C9 C5 C6 O1 . . . . 25.17(17) ?
C4 C5 C6 C7 . . . . 25.5(2) ?
C9 C5 C6 C7 . . . . 140.73(15) ?
C4 C5 C6 C11 . . . . 151.19(16) ?
C9 C5 C6 C11 . . . . -93.59(17) ?
O1 C6 C7 C12 . . . . 105.9(2) ?
C11 C6 C7 C12 . . . . -135.7(2) ?
C5 C6 C7 C12 . . . . -8.7(3) ?
O3 C3 C8 C9 . . . . 79.34(19) ?
C2 C3 C8 C9 . . . . -160.14(16) ?
C4 C3 C8 C9 . . . . -38.51(19) ?
C3 C8 C9 C10 . . . . -88.70(18) ?
C3 C8 C9 C5 . . . . 25.1(2) ?
C6 C5 C9 C10 . . . . -2.18(18) ?
C4 C5 C9 C10 . . . . 119.92(16) ?
C6 C5 C9 C8 . . . . -123.09(16) ?
C4 C5 C9 C8 . . . . -1.0(2) ?
C6 O1 C10 C9 . . . . 39.32(19) ?
C8 C9 C10 O1 . . . . 92.57(18) ?
C5 C9 C10 O1 . . . . -22.02(19) ?
C6 C7 C12 C13 . . . . -0.7(3) ?
C7 C12 C13 O2 . . . . 174.12(19) ?
C7 C12 C13 C4 . . . . -7.7(3) ?
C5 C4 C13 O2 . . . . -156.98(18) ?
C3 C4 C13 O2 . . . . 81.4(2) ?
C5 C4 C13 C12 . . . . 24.8(2) ?
C3 C4 C13 C12 . . . . -96.81(19) ?
