#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:42:44 +0300 (Sun, 04 Oct 2020) $
#$Revision: 256987 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517829.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_4517829
loop_
_publ_author_name
'Mao, Ying'
'Wang, Zehua'
'Wang, Gang'
'Zhao, Ran'
'Kan, Linglong'
'Pan, Xiaoguang'
'Liu, Lei'
_publ_section_title
;
 Redox Deracemization of Tertiary Stereocenters Adjacent to an
 Electron-Withdrawing Group
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              7785
_journal_page_last               7791
_journal_paper_doi               10.1021/acscatal.0c02486
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H13 N O'
_chemical_formula_sum            'C15 H13 N O'
_chemical_formula_weight         223.26
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.652(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6989(2)
_cell_length_b                   5.6085(2)
_cell_length_c                   13.5280(4)
_cell_measurement_reflns_used    5588
_cell_measurement_temperature    172.99(10)
_cell_measurement_theta_max      76.4260
_cell_measurement_theta_min      3.2230
_cell_volume                     583.50(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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      172.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -90.00 -63.00   1.00    0.10    --  -48.45 -15.00  -3.00   27
  2  ω      5.00  30.00   1.00    0.10    --   48.45 -15.00  -3.00   25
  3  ω     59.00  97.00   1.00    0.10    --   48.45  15.00 166.00   38
  4  ω    -87.00 -55.00   1.00    0.40    --  -86.25  15.00 166.00   32
  5  ω   -118.00 -90.00   1.00    0.40    --  -86.25 -15.00  -3.00   28
  6  ω     60.00 102.00   1.00    0.40    --  106.49 -15.00  -3.00   42
  7  ω    142.00 168.00   1.00    0.40    --  106.49  15.00 166.00   26
  8  ω     95.00 139.00   1.00    0.40    --  106.49  15.00 166.00   44
  9  ω    -55.00 -26.00   1.00    0.10    --  -48.45 -77.00 -90.00   29
 10  ω    -66.00 -12.00   1.00    0.10    --  -48.45 125.00-120.00   54
 11  ω    -80.00 -36.00   1.00    0.10    --  -48.45 -19.00-120.00   44
 12  ω    -60.00 -28.00   1.00    0.10    --  -48.45 -77.00 -30.00   32
 13  ω    -70.00 -33.00   1.00    0.10    --  -48.45 -77.00-180.00   37
 14  ω    -53.00 -28.00   1.00    0.10    --  -48.45 -77.00-120.00   25
 15  ω    -42.00 -16.00   1.00    0.10    --  -48.45  15.00 166.00   26
 16  ω    -59.00 -34.00   1.00    0.10    --  -48.45 -77.00-150.00   25
 17  ω     42.00  67.00   1.00    0.10    --   48.45  37.00 -90.00   25
 18  ω    -77.00 -15.00   1.00    0.40    --  -86.25  61.00-120.00   62
 19  ω    -87.00 -62.00   1.00    0.40    --  -86.25 -79.00 -55.92   25
 20  ω   -117.00 -74.00   1.00    0.40    --  -86.25 -61.00 -60.00   43
 21  ω    -47.00 -13.00   1.00    0.40    --  -86.25  77.00  30.00   34
 22  ω    -88.00 -62.00   1.00    0.40    --  -86.25 -81.00 -71.32   26
 23  ω   -155.00 -73.00   1.00    0.40    --  -86.25 -61.00 -90.00   82
 24  ω    -96.00 -65.00   1.00    0.40    --  -86.25 -81.00-100.72   31
 25  ω    -95.00 -70.00   1.00    0.40    --  -86.25 -59.00 -47.05   25
 26  ω   -123.00 -65.00   1.00    0.40    --  -86.25 -72.00-136.57   58
 27  ω    -89.00 -64.00   1.00    0.40    --  -86.25 -75.00 -55.24   25
 28  ω    -88.00 -63.00   1.00    0.40    --  -86.25 -77.00 -30.00   25
 29  ω    -88.00 -63.00   1.00    0.40    --  -86.25 -77.00 -90.00   25
 30  ω    -97.00 -72.00   1.00    0.40    --  -86.25 -55.00 -48.69   25
 31  ω   -116.00 -65.00   1.00    0.40    --  -86.25 -72.00-149.76   51
 32  ω    -89.00 -64.00   1.00    0.40    --  -86.25 -77.00-120.00   25
 33  ω    -89.00 -64.00   1.00    0.40    --  -86.25 -77.00-150.00   25
 34  ω   -113.00 -63.00   1.00    0.40    --  -86.25 -80.00 -93.54   50
 35  ω    110.00 135.00   1.00    0.40    --  106.49  45.00 -30.00   25
 36  ω     50.00  99.00   1.00    0.40    --  106.49 -94.00-180.00   49
 37  ω     37.00 107.00   1.00    0.40    --  106.49 -94.00 120.00   70
 38  ω     35.00 113.00   1.00    0.40    --  106.49 -61.00  60.00   78
 39  ω    101.00 126.00   1.00    0.40    --  106.49  61.00-120.00   25
 40  ω    110.00 171.00   1.00    0.40    --  106.49  77.00 -30.00   61
 41  ω     54.00 108.00   1.00    0.40    --  106.49 -94.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356842000
_diffrn_orient_matrix_UB_12      -0.0079829000
_diffrn_orient_matrix_UB_13      -0.1110179000
_diffrn_orient_matrix_UB_21      -0.1933152000
_diffrn_orient_matrix_UB_22      -0.0556023000
_diffrn_orient_matrix_UB_23      -0.0244699000
_diffrn_orient_matrix_UB_31      -0.0389156000
_diffrn_orient_matrix_UB_32      0.2688278000
_diffrn_orient_matrix_UB_33      -0.0082955000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6647
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.270
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75556
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0307
_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)+(0.0475P)²+0.0743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                1975
_reflns_number_total             2043
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02486_si_002.cif
_cod_data_source_block           190415c
_cod_depositor_comments          'Adding full bibliography for 4517829.cif.'
_cod_database_code               4517829
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         CNO
_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   0.981
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.524
_oxdiff_exptl_absorpt_empirical_full_min 0.691
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 0.95619(17) 0.6393(3) 0.95368(10) 0.0381(4) Uani 1 1 d . . . . .
H1 H 0.9771 0.5347 0.9971 0.057 Uiso 1 1 calc GR . . . .
N1 N 0.1175(2) 0.1564(4) 0.83042(12) 0.0394(5) Uani 1 1 d . . . . .
C1 C 0.2245(3) 0.7393(5) 0.35782(16) 0.0462(6) Uani 1 1 d . . . . .
H1A H 0.3012 0.6310 0.3234 0.069 Uiso 1 1 calc GR . . . .
H1B H 0.2590 0.9046 0.3458 0.069 Uiso 1 1 calc GR . . . .
H1C H 0.1041 0.7152 0.3331 0.069 Uiso 1 1 calc GR . . . .
C2 C 0.2385(2) 0.6887(4) 0.46752(15) 0.0330(5) Uani 1 1 d . . . . .
C3 C 0.3195(3) 0.4858(5) 0.50609(15) 0.0367(5) Uani 1 1 d . . . . .
H3 H 0.3702 0.3756 0.4625 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3279(3) 0.4408(4) 0.60728(15) 0.0343(5) Uani 1 1 d . . . . .
H4 H 0.3842 0.3008 0.6320 0.041 Uiso 1 1 calc R . . . .
C5 C 0.2549(2) 0.5986(4) 0.67225(14) 0.0276(4) Uani 1 1 d . . . . .
C6 C 0.1716(3) 0.7998(4) 0.63396(16) 0.0367(5) Uani 1 1 d . . . . .
H6 H 0.1190 0.9085 0.6774 0.044 Uiso 1 1 calc R . . . .
C7 C 0.1643(3) 0.8441(4) 0.53304(16) 0.0384(5) Uani 1 1 d . . . . .
H7 H 0.1074 0.9836 0.5084 0.046 Uiso 1 1 calc R . . . .
C8 C 0.2666(2) 0.5585(4) 0.78461(14) 0.0283(4) Uani 1 1 d . . . . .
H8 H 0.1995 0.6898 0.8152 0.034 Uiso 1 1 calc R . . . .
C9 C 0.1822(3) 0.3331(4) 0.80985(14) 0.0309(5) Uani 1 1 d . . . . .
C10 C 0.4525(2) 0.5690(4) 0.83024(13) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.5188(3) 0.3981(4) 0.89592(15) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.4487 0.2660 0.9126 0.037 Uiso 1 1 calc R . . . .
C12 C 0.6866(3) 0.4180(4) 0.93764(15) 0.0333(5) Uani 1 1 d . . . . .
H12 H 0.7307 0.2996 0.9823 0.040 Uiso 1 1 calc R . . . .
C13 C 0.7893(2) 0.6099(4) 0.91408(13) 0.0293(5) Uani 1 1 d . . . . .
C14 C 0.7256(3) 0.7817(4) 0.84924(15) 0.0355(5) Uani 1 1 d . . . . .
H14 H 0.7961 0.9137 0.8329 0.043 Uiso 1 1 calc R . . . .
C15 C 0.5579(3) 0.7609(4) 0.80779(16) 0.0348(5) Uani 1 1 d . . . . .
H15 H 0.5144 0.8800 0.7633 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'
N N 0.0311 0.0180 '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
C3 C2 C1 122.3(2) . . ?
C7 C2 C1 119.9(2) . . ?
C7 C2 C3 117.82(19) . . ?
C2 C3 C4 121.2(2) . . ?
C5 C4 C3 120.5(2) . . ?
C4 C5 C6 118.51(18) . . ?
C4 C5 C8 121.89(18) . . ?
C6 C5 C8 119.59(18) . . ?
C7 C6 C5 120.7(2) . . ?
C2 C7 C6 121.2(2) . . ?
C9 C8 C5 110.49(16) . . ?
C9 C8 C10 110.74(16) . . ?
C10 C8 C5 113.80(15) . . ?
N1 C9 C8 179.2(2) . . ?
C11 C10 C8 122.69(17) . . ?
C11 C10 C15 118.26(17) . . ?
C15 C10 C8 119.02(17) . . ?
C10 C11 C12 120.80(19) . . ?
C13 C12 C11 119.98(18) . . ?
O1 C13 C12 122.42(18) . . ?
C14 C13 O1 117.51(19) . . ?
C14 C13 C12 120.07(18) . . ?
C13 C14 C15 119.7(2) . . ?
C14 C15 C10 121.20(19) . . ?
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 C13 1.379(2) . ?
N1 C9 1.149(3) . ?
C1 C2 1.510(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.386(3) . ?
C5 C8 1.535(3) . ?
C6 C7 1.386(3) . ?
C8 C9 1.468(3) . ?
C8 C10 1.534(3) . ?
C10 C11 1.388(3) . ?
C10 C15 1.390(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.389(3) . ?
