#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:52:38 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260685 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/74/7127411.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_7127411
loop_
_publ_author_name
'Xu, Huacheng'
'Nazli, Adila'
'Zou, Cheng'
'Wang, Zhi-Peng'
'He, Yun'
_publ_section_title
;
 Bench-stable imine surrogates for the one-pot and catalytic asymmetric
 synthesis of α-amino esters/ketones.
;
_journal_issue                   91
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14243
_journal_page_last               14246
_journal_paper_doi               10.1039/d0cc06055k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H23 Cl2 N O6'
_chemical_formula_sum            'C23 H23 Cl2 N O6'
_chemical_formula_weight         480.32
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2020-06-02 deposited with the CCDC.	2020-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   12.39590(15)
_cell_length_b                   12.39590(15)
_cell_length_c                   13.34104(13)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    293.07(10)
_cell_measurement_theta_max      71.6830
_cell_measurement_theta_min      4.1090
_cell_volume                     1775.32(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.07(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0243
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00  -7.00   1.00    1.00    --  -35.97 -19.00 -60.00   99
  2  ω     24.00  90.00   1.00    1.00    --   35.97-126.00  90.00   66
  3  ω    -31.00  53.00   1.00    1.00    --   35.97 -57.00-120.00   84
  4  ω     91.00 176.00   1.00    3.00    --  107.97  45.00  90.00   85
  5  ω     38.00 112.00   1.00    3.00    --  107.97-112.00-180.00   74
  6  ω     41.00 126.00   1.00    3.00    --  107.97 -61.00-120.00   85
  7  ω     38.00 129.00   1.00    3.00    --  107.97 -30.00 -60.00   91
  8  ω   -105.00 -17.00   1.00    1.00    --  -35.97 -38.00-180.00   88
  9  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00 -90.00   84
 10  ω   -103.00 -19.00   1.00    1.00    --  -35.97 -57.00  90.00   84
 11  ω     87.00 112.00   1.00    3.00    --  107.97  30.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1239942000
_diffrn_orient_matrix_UB_12      0.0362170000
_diffrn_orient_matrix_UB_13      -0.0529742000
_diffrn_orient_matrix_UB_21      0.0490297000
_diffrn_orient_matrix_UB_22      -0.0286446000
_diffrn_orient_matrix_UB_23      0.0966268000
_diffrn_orient_matrix_UB_31      -0.0530948000
_diffrn_orient_matrix_UB_32      -0.1358749000
_diffrn_orient_matrix_UB_33      -0.0345169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6370
_diffrn_reflns_point_group_measured_fraction_full 0.789
_diffrn_reflns_point_group_measured_fraction_max 0.757
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.759
_diffrn_reflns_theta_min         4.118
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (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    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0542
_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)+(0.1089P)²+0.0371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.555
_reflns_Friedel_fraction_full    0.578
_reflns_Friedel_fraction_max     0.541
_reflns_number_gt                3413
_reflns_number_total             3530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc06055k2.cif
_cod_data_source_block           zzl_200521
_cod_depositor_comments          'Adding full bibliography for 7127411.cif.'
_cod_original_cell_volume        1775.32(5)
_cod_database_code               7127411
_chemical_oxdiff_formula         'C23 H22 Cl2 N O6'
_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.
;
_reflns_odcompleteness_completeness 99.95
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C20(H20), C19(H19), C13(H13), C23(H23), C15(H15), C22(H22),
 C12(H12)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2017/1
_olex2_date_sample_data_collection 2020-05-21
_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.657
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
Cl1 Cl -0.18988(17) -0.68150(16) -0.43081(14) 0.0958(5) Uani 1 1 d . . . . .
Cl2 Cl 0.28172(17) 0.0492(2) -1.00654(13) 0.1100(7) Uani 1 1 d . . . . .
O6 O -0.4967(2) -0.2236(3) -0.93982(17) 0.0490(6) Uani 1 1 d . . . . .
O5 O -0.2848(3) -0.1077(3) -0.9409(2) 0.0528(6) Uani 1 1 d . . . . .
C4 C -0.3829(3) -0.1717(3) -0.8990(2) 0.0390(7) Uani 1 1 d . . . . .
O1 O -0.2759(3) -0.3792(3) -0.8363(3) 0.0663(8) Uani 1 1 d . . . . .
O4 O -0.4018(4) -0.0652(4) -0.6511(3) 0.0704(10) Uani 1 1 d . . . . .
N1 N -0.3947(3) -0.2031(3) -0.8009(2) 0.0461(7) Uani 1 1 d . . . . .
H1 H -0.466806 -0.257003 -0.778335 0.055 Uiso 1 1 calc R . . . .
O2 O -0.4455(3) -0.3755(4) -0.6440(3) 0.0695(10) Uani 1 1 d . . . . .
O3 O -0.2672(4) -0.0917(4) -0.5597(2) 0.0784(12) Uani 1 1 d . . . . .
C18 C -0.0802(4) -0.1948(3) -0.8470(2) 0.0407(7) Uani 1 1 d . . . . .
C17 C -0.2035(4) -0.2789(4) -0.7993(3) 0.0440(7) Uani 1 1 d . . . . .
C14 C -0.2332(5) -0.5870(4) -0.4962(4) 0.0598(10) Uani 1 1 d . . . . .
C2 C -0.3186(4) -0.1004(4) -0.6374(3) 0.0480(8) Uani 1 1 d . . . . .
C3 C -0.2898(4) -0.1489(3) -0.7327(2) 0.0428(7) Uani 1 1 d . . . . .
H3 H -0.221661 -0.077141 -0.766848 0.051 Uiso 1 1 calc R . . . .
C9 C -0.2412(3) -0.2375(3) -0.7044(2) 0.0416(7) Uani 1 1 d . . . . .
H9 H -0.167451 -0.192260 -0.661726 0.050 Uiso 1 1 calc R . . . .
C10 C -0.3382(3) -0.3524(4) -0.6475(3) 0.0464(8) Uani 1 1 d . . . . .
C11 C -0.2981(3) -0.4336(4) -0.5977(3) 0.0449(8) Uani 1 1 d . . . . .
C16 C -0.1738(4) -0.3956(4) -0.5794(4) 0.0590(10) Uani 1 1 d . . . . .
H16 H -0.111873 -0.317929 -0.601503 0.071 Uiso 1 1 calc R . . . .
C20 C 0.1209(5) -0.0082(5) -0.8529(4) 0.0620(11) Uani 1 1 d . . . . .
H20 H 0.180280 0.066627 -0.824328 0.074 Uiso 1 1 calc R . . . .
C19 C 0.0094(4) -0.0834(4) -0.8048(3) 0.0495(8) Uani 1 1 d . . . . .
H19 H -0.006077 -0.058853 -0.743120 0.059 Uiso 1 1 calc R . . . .
C5 C -0.5159(4) -0.2194(4) -1.0487(3) 0.0519(9) Uani 1 1 d . . . . .
C13 C -0.3570(5) -0.6285(5) -0.5141(5) 0.0705(13) Uani 1 1 d . . . . .
H13 H -0.418043 -0.707112 -0.492801 0.085 Uiso 1 1 calc R . . . .
C23 C -0.0545(4) -0.2314(5) -0.9387(3) 0.0559(10) Uani 1 1 d . . . . .
H23 H -0.113264 -0.306490 -0.967360 0.067 Uiso 1 1 calc R . . . .
C15 C -0.1415(5) -0.4728(5) -0.5284(5) 0.0697(13) Uani 1 1 d . . . . .
H15 H -0.058261 -0.447162 -0.516125 0.084 Uiso 1 1 calc R . . . .
C22 C 0.0567(5) -0.1580(5) -0.9873(3) 0.0645(12) Uani 1 1 d . . . . .
H22 H 0.073562 -0.182984 -1.048139 0.077 Uiso 1 1 calc R . . . .
C21 C 0.1429(4) -0.0461(5) -0.9440(3) 0.0613(11) Uani 1 1 d . . . . .
C12 C -0.3890(4) -0.5509(4) -0.5645(4) 0.0616(11) Uani 1 1 d . . . . .
H12 H -0.472550 -0.577487 -0.576419 0.074 Uiso 1 1 calc R . . . .
C7 C -0.4540(6) -0.0888(6) -1.0874(4) 0.0840(18) Uani 1 1 d . . . . .
H7A H -0.473070 -0.038770 -1.044068 0.126 Uiso 1 1 calc GR . . . .
H7B H -0.483725 -0.088485 -1.153765 0.126 Uiso 1 1 calc GR . . . .
H7C H -0.365494 -0.055395 -1.089173 0.126 Uiso 1 1 calc GR . . . .
C6 C -0.6570(5) -0.2808(6) -1.0558(4) 0.0710(13) Uani 1 1 d . . . . .
H6A H -0.694760 -0.358825 -1.020667 0.107 Uiso 1 1 calc GR . . . .
H6B H -0.681671 -0.295087 -1.124941 0.107 Uiso 1 1 calc GR . . . .
H6C H -0.683422 -0.227218 -1.026320 0.107 Uiso 1 1 calc GR . . . .
C8 C -0.4681(6) -0.2971(6) -1.0998(4) 0.0778(16) Uani 1 1 d . . . . .
H8A H -0.383295 -0.267336 -1.080234 0.117 Uiso 1 1 calc GR . . . .
H8B H -0.472277 -0.290187 -1.171213 0.117 Uiso 1 1 calc GR . . . .
H8C H -0.518525 -0.382686 -1.080284 0.117 Uiso 1 1 calc GR . . . .
C1 C -0.4290(8) -0.0110(8) -0.5642(6) 0.096(2) Uani 1 1 d . . . . .
H1A H -0.493711 0.006898 -0.581036 0.144 Uiso 1 1 calc GR . . . .
H1B H -0.355296 0.064565 -0.545150 0.144 Uiso 1 1 calc GR . . . .
H1C H -0.455877 -0.068977 -0.509456 0.144 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.3639 0.7018 '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
C4 O6 C5 122.2(3) . . ?
O6 C4 N1 108.6(3) . . ?
O5 C4 O6 126.9(3) . . ?
O5 C4 N1 124.5(3) . . ?
C2 O4 C1 116.2(4) . . ?
C4 N1 C3 122.1(3) . . ?
C19 C18 C17 123.5(3) . . ?
C19 C18 C23 118.7(4) . . ?
C23 C18 C17 117.8(4) . . ?
O1 C17 C18 121.0(3) . . ?
O1 C17 C9 119.2(4) . . ?
C18 C17 C9 119.8(3) . . ?
C13 C14 Cl1 119.8(4) . . ?
C15 C14 Cl1 118.4(4) . . ?
C15 C14 C13 121.8(4) . . ?
O4 C2 C3 113.1(3) . . ?
O3 C2 O4 124.1(4) . . ?
O3 C2 C3 122.7(4) . . ?
N1 C3 C2 112.0(3) . . ?
N1 C3 C9 113.8(3) . . ?
C2 C3 C9 109.2(3) . . ?
C17 C9 C3 109.3(3) . . ?
C17 C9 C10 109.2(3) . . ?
C10 C9 C3 112.3(3) . . ?
O2 C10 C9 119.8(4) . . ?
O2 C10 C11 121.5(4) . . ?
C11 C10 C9 118.7(3) . . ?
C16 C11 C10 122.7(3) . . ?
C16 C11 C12 118.7(4) . . ?
C12 C11 C10 118.6(4) . . ?
C15 C16 C11 120.4(4) . . ?
C21 C20 C19 118.8(4) . . ?
C20 C19 C18 121.1(4) . . ?
O6 C5 C7 111.9(4) . . ?
O6 C5 C6 102.1(3) . . ?
O6 C5 C8 107.4(4) . . ?
C7 C5 C6 111.1(5) . . ?
C7 C5 C8 112.3(5) . . ?
C8 C5 C6 111.7(4) . . ?
C14 C13 C12 118.6(4) . . ?
C22 C23 C18 120.9(4) . . ?
C14 C15 C16 119.4(5) . . ?
C23 C22 C21 118.9(4) . . ?
C20 C21 Cl2 119.3(4) . . ?
C20 C21 C22 121.6(4) . . ?
C22 C21 Cl2 119.1(4) . . ?
C13 C12 C11 121.1(4) . . ?
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
Cl1 C14 1.746(5) . ?
Cl2 C21 1.738(5) . ?
O6 C4 1.339(4) . ?
O6 C5 1.477(4) . ?
O5 C4 1.207(5) . ?
C4 N1 1.351(4) . ?
O1 C17 1.216(5) . ?
O4 C2 1.318(5) . ?
O4 C1 1.461(6) . ?
N1 C3 1.448(5) . ?
O2 C10 1.213(5) . ?
O3 C2 1.193(5) . ?
C18 C17 1.495(5) . ?
C18 C19 1.387(5) . ?
C18 C23 1.396(5) . ?
C17 C9 1.525(5) . ?
C14 C13 1.373(7) . ?
C14 C15 1.368(7) . ?
C2 C3 1.523(5) . ?
C3 C9 1.541(5) . ?
C9 C10 1.529(5) . ?
C10 C11 1.484(5) . ?
C11 C16 1.389(6) . ?
C11 C12 1.393(6) . ?
C16 C15 1.386(7) . ?
C20 C19 1.380(6) . ?
C20 C21 1.378(7) . ?
C5 C7 1.495(7) . ?
C5 C6 1.521(6) . ?
C5 C8 1.521(7) . ?
C13 C12 1.385(7) . ?
C23 C22 1.375(7) . ?
C22 C21 1.384(8) . ?
