#------------------------------------------------------------------------------
#$Date: 2022-08-06 14:38:14 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567166.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_1567166
loop_
_publ_author_name
'Zhang, Chang-Sheng'
'Shao, Ya-Ping'
'Zhang, Fu-Min'
'Han, Xue'
'Zhang, Xiao-Ming'
'Zhang, Kun'
'Tu, Yong-Qiang'
_publ_section_title
;
 Cu(ii)/SPDO complex catalyzed asymmetric Baeyer-Villiger oxidation of
 2-arylcyclobutanones and its application for the total synthesis of
 eupomatilones 5 and 6.
;
_journal_issue                   28
_journal_name_full               'Chemical science'
_journal_page_first              8429
_journal_page_last               8435
_journal_paper_doi               10.1039/d2sc02079c
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 O3'
_chemical_formula_sum            'C12 H12 O3'
_chemical_formula_weight         204.22
_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_creation_date             2022-04-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-04-28 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7960(2)
_cell_length_b                   10.4133(2)
_cell_length_c                   10.7857(2)
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.6670
_cell_measurement_theta_min      4.1060
_cell_volume                     987.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  22.00   0.50    0.05    --   47.57 -19.00  60.00   86
  2  ω     36.00  61.00   0.50    0.05    --  107.75 -57.00 120.00   50
  3  ω    127.00 172.00   0.50    0.05    --  107.75  37.00-150.00   90
  4  ω     98.00 124.00   0.50    0.05    --  107.75  37.00-150.00   52
  5  ω    -24.00  10.00   0.50    0.05    --  -47.57  17.00 -69.00   68
  6  ω    -10.00  28.00   0.50    0.05    --  -47.57  19.00  60.00   76
  7  ω    -44.00   8.00   0.50    0.05    --  -47.57  37.00  30.00  104
  8  ω   -112.00 -55.00   0.50    0.05    -- -100.00 133.00 147.00  114
  9  ω   -149.00-109.00   0.50    0.05    -- -100.00 -17.00 121.00   80
 10  ω   -167.00-139.00   0.50    0.05    -- -100.00-109.00 -24.00   56
 11  ω     78.00 106.00   0.50    0.05    --  107.75-125.00  30.00   56
 12  ω     35.00  61.00   0.50    0.05    --  107.75-125.00   0.00   52
 13  ω     35.00  71.00   0.50    0.05    --  107.75-125.00  30.00   72
 14  ω     71.00 102.00   0.50    0.05    --  107.75-125.00   0.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344154000
_diffrn_orient_matrix_UB_12      -0.1321906000
_diffrn_orient_matrix_UB_13      0.0574493000
_diffrn_orient_matrix_UB_21      0.0159795000
_diffrn_orient_matrix_UB_22      -0.0579983000
_diffrn_orient_matrix_UB_23      -0.1309105000
_diffrn_orient_matrix_UB_31      0.1708422000
_diffrn_orient_matrix_UB_32      0.0322976000
_diffrn_orient_matrix_UB_33      0.0007956000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3439
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.354
_diffrn_reflns_theta_min         5.907
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 610 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.877
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0298
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.548
_reflns_Friedel_fraction_full    0.822
_reflns_Friedel_fraction_max     0.720
_reflns_number_gt                1732
_reflns_number_total             1765
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02079c3.cif
_cod_data_source_block           zhangchsh_0412_1_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 1567165--1567169.cif.
;
_cod_database_code               1567166
_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   0.909
_shelx_estimated_absorpt_t_min   0.875
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.529
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 0.48782(15) 0.42239(12) 1.00560(10) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.30401(11) 0.24364(10) 0.46822(10) 0.0288(3) Uani 1 1 d . . . . .
O3 O 0.33331(16) 0.13272(15) 0.29346(12) 0.0496(4) Uani 1 1 d . . . . .
C1 C 0.41456(18) 0.38987(15) 0.89799(14) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.30040(18) 0.46171(15) 0.84432(14) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.268660 0.541235 0.878850 0.039 Uiso 1 1 calc R . . . .
C3 C 0.23361(17) 0.41240(14) 0.73709(14) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.154607 0.459489 0.697843 0.035 Uiso 1 1 calc R . . . .
C4 C 0.27985(17) 0.29587(14) 0.68612(12) 0.0254(3) Uani 1 1 d . . . . .
C5 C 0.39945(16) 0.22705(14) 0.74126(13) 0.0267(3) Uani 1 1 d . . . . .
H5 H 0.434029 0.148774 0.705881 0.032 Uiso 1 1 calc R . . . .
C6 C 0.46616(16) 0.27496(14) 0.84788(13) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.59447(18) 0.22771(16) 0.92871(15) 0.0355(4) Uani 1 1 d . . . . .
H7A H 0.694999 0.248297 0.892547 0.043 Uiso 1 1 calc R . . . .
H7B H 0.587502 0.134117 0.943809 0.043 Uiso 1 1 calc R . . . .
C8 C 0.56420(19) 0.30484(19) 1.04666(16) 0.0394(4) Uani 1 1 d . . . . .
H8A H 0.498452 0.255812 1.104180 0.047 Uiso 1 1 calc R . . . .
H8B H 0.660761 0.325522 1.089382 0.047 Uiso 1 1 calc R . . . .
C9 C 0.19876(15) 0.24467(13) 0.57463(13) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.111616 0.302867 0.554924 0.032 Uiso 1 1 calc R . . . .
C10 C 0.26882(18) 0.14566(15) 0.39069(15) 0.0333(4) Uani 1 1 d . . . . .
C11 C 0.14226(19) 0.06682(15) 0.44572(16) 0.0375(4) Uani 1 1 d . . . . .
H11A H 0.163449 -0.026148 0.437360 0.045 Uiso 1 1 calc R . . . .
H11B H 0.044058 0.086413 0.405065 0.045 Uiso 1 1 calc R . . . .
C12 C 0.14005(18) 0.10687(15) 0.58128(15) 0.0350(4) Uani 1 1 d . . . . .
H12A H 0.207875 0.052027 0.631894 0.042 Uiso 1 1 calc R . . . .
H12B H 0.035872 0.103483 0.615858 0.042 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
C1 O1 C8 105.39(12) . . ?
C10 O2 C9 110.03(11) . . ?
O1 C1 C2 124.32(14) . . ?
O1 C1 C6 112.88(13) . . ?
C2 C1 C6 122.79(14) . . ?
C1 C2 C3 117.06(14) . . ?
C4 C3 C2 121.66(14) . . ?
C3 C4 C5 119.73(13) . . ?
C3 C4 C9 119.23(13) . . ?
C5 C4 C9 121.02(12) . . ?
C6 C5 C4 119.03(13) . . ?
C1 C6 C7 107.49(13) . . ?
C5 C6 C1 119.69(14) . . ?
C5 C6 C7 132.82(15) . . ?
C6 C7 C8 100.33(13) . . ?
O1 C8 C7 105.52(13) . . ?
O2 C9 C4 109.20(10) . . ?
O2 C9 C12 104.01(11) . . ?
C4 C9 C12 117.28(12) . . ?
O2 C10 C11 109.65(13) . . ?
O3 C10 O2 121.06(16) . . ?
O3 C10 C11 129.27(15) . . ?
C10 C11 C12 103.83(12) . . ?
C11 C12 C9 102.02(12) . . ?
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 1.3700(18) . ?
O1 C8 1.465(2) . ?
O2 C9 1.4745(16) . ?
O2 C10 1.3550(18) . ?
O3 C10 1.200(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.389(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.405(2) . ?
C4 C9 1.4963(18) . ?
C5 C6 1.3841(19) . ?
C6 C7 1.509(2) . ?
C7 C8 1.528(2) . ?
C9 C12 1.527(2) . ?
C10 C11 1.505(2) . ?
C11 C12 1.521(2) . ?
