#------------------------------------------------------------------------------
#$Date: 2020-04-07 02:27:16 +0300 (Tue, 07 Apr 2020) $
#$Revision: 250422 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/81/4038194.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_4038194
loop_
_publ_author_name
'Zhang, Yue'
'Li, Jun-Kuan'
'Zhang, Fa-Guang'
'Ma, Jun-An'
_publ_section_title
;
 Catalytic Asymmetric Access to Noncanonical Chiral α-Amino Acids from
 Cyclic Iminoglyoxylates and Enamides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00436
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 Cl N O3'
_chemical_formula_sum            'C24 H20 Cl N O3'
_chemical_formula_weight         405.86
_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   mixed
_audit_creation_date             2018-10-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.416(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2465(3)
_cell_length_b                   7.9689(3)
_cell_length_c                   13.2794(6)
_cell_measurement_reflns_used    6850
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      28.7100
_cell_measurement_theta_min      2.2180
_cell_volume                     965.30(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      4.00  30.00   0.50    3.00    --    5.07 -98.00  -8.00   52
  2  ω      5.00  30.00   0.50    3.00    --    5.07  98.00  98.00   50
  3  ω    -25.00  40.00   0.50    3.00    --    5.07 -99.00 -60.00  130
  4  ω    -18.00   8.00   0.50    3.00    --    5.07 -99.00-150.00   52
  5  ω     -8.00  79.00   0.50    3.00    --    5.07  37.00 -60.00  174
  6  ω    -23.00  24.00   0.50    3.00    --   -6.71 -99.00  90.00   94
  7  ω    -22.00   5.00   0.50    3.00    --   -6.79 -98.00  -9.00   54
  8  ω    -61.00   2.00   0.50    3.00    --   -6.79 -57.00-120.00  126
  9  ω    -26.00   0.00   0.50    3.00    --   -6.79 -99.00 -30.00   52
 10  ω    -78.00  -7.00   0.50    3.00    --   -6.79 -77.00  60.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0515337000
_diffrn_orient_matrix_UB_12      0.0599082000
_diffrn_orient_matrix_UB_13      -0.0116720000
_diffrn_orient_matrix_UB_21      -0.0265090000
_diffrn_orient_matrix_UB_22      0.0588611000
_diffrn_orient_matrix_UB_23      0.0326806000
_diffrn_orient_matrix_UB_31      0.0518152000
_diffrn_orient_matrix_UB_32      -0.0295113000
_diffrn_orient_matrix_UB_33      0.0415601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15330
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.794
_diffrn_reflns_theta_min         2.233
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1536 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4868
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0429
_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)+(0.0413P)²+0.0496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0926
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                4052
_reflns_number_total             4868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00436_si_002.cif
_cod_data_source_block           zy_346_1b
_cod_database_code               4038194
_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   0.978
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C8(H8a,H8b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C22(H22), C18(H18), C24(H24), C14(H14), C20(H20), C23(H23), C2(H2),
 C15(H15), C17(H17), C16(H16), C21(H21), C3(H3), C4(H4)
;
_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 1.162
_oxdiff_exptl_absorpt_empirical_full_min 0.892
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
Cl1 Cl 0.64641(8) 0.26543(9) 1.01324(6) 0.0330(2) Uani 1 1 d . . . . .
O3 O 0.12139(19) 0.8093(2) 0.37480(15) 0.0195(4) Uani 1 1 d . . . . .
O1 O 0.47320(19) 0.5766(3) 0.67054(15) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.0043(2) 0.8098(2) 0.50712(16) 0.0224(4) Uani 1 1 d . . . . .
N1 N 0.2685(2) 0.5259(3) 0.45927(17) 0.0175(5) Uani 1 1 d . . . . .
C1 C 0.3467(3) 0.4545(3) 0.7917(2) 0.0176(5) Uani 1 1 d . . . . .
C10 C 0.1114(3) 0.7687(4) 0.4728(2) 0.0182(5) Uani 1 1 d . . . . .
C19 C 0.1979(3) 0.4697(3) 0.2768(2) 0.0186(6) Uani 1 1 d . . . . .
C12 C 0.2940(3) 0.5779(3) 0.3561(2) 0.0168(5) Uani 1 1 d . . . . .
C6 C 0.4795(3) 0.4099(3) 0.8518(2) 0.0202(6) Uani 1 1 d . . . . .
H6 H 0.567758 0.436214 0.830567 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3543(3) 0.5441(3) 0.6943(2) 0.0179(5) Uani 1 1 d . . . . .
C9 C 0.2391(3) 0.6648(3) 0.5261(2) 0.0169(5) Uani 1 1 d . . . . .
H9 H 0.326101 0.736863 0.538179 0.020 Uiso 1 1 calc R . . . .
C8 C 0.2125(3) 0.5971(4) 0.6279(2) 0.0181(5) Uani 1 1 d . . . . .
H8A H 0.146969 0.501472 0.616579 0.022 Uiso 1 1 calc R . . . .
H8B H 0.165358 0.682743 0.663046 0.022 Uiso 1 1 calc R . . . .
C22 C 0.0247(3) 0.2575(4) 0.1374(2) 0.0235(6) Uani 1 1 d . . . . .
H22 H -0.032424 0.187313 0.090945 0.028 Uiso 1 1 calc R . . . .
C18 C 0.5051(3) 0.5238(4) 0.2566(2) 0.0213(6) Uani 1 1 d . . . . .
H18 H 0.436622 0.502287 0.198555 0.026 Uiso 1 1 calc R . . . .
C24 C 0.0864(3) 0.5342(4) 0.2040(2) 0.0216(6) Uani 1 1 d . . . . .
H24 H 0.068688 0.649109 0.201571 0.026 Uiso 1 1 calc R . . . .
C14 C 0.5619(3) 0.5944(3) 0.4341(2) 0.0204(6) Uani 1 1 d . . . . .
H14 H 0.531859 0.618619 0.495988 0.025 Uiso 1 1 calc R . . . .
C20 C 0.2205(3) 0.2961(3) 0.2793(2) 0.0218(6) Uani 1 1 d . . . . .
H20 H 0.293952 0.250323 0.327691 0.026 Uiso 1 1 calc R . . . .
C5 C 0.4794(3) 0.3270(4) 0.9426(2) 0.0238(6) Uani 1 1 d . . . . .
C23 C 0.0011(3) 0.4286(4) 0.1346(2) 0.0231(6) Uani 1 1 d . . . . .
H23 H -0.072423 0.473823 0.086031 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2155(3) 0.4149(3) 0.8250(2) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.126385 0.441327 0.784730 0.026 Uiso 1 1 calc R . . . .
C15 C 0.7103(3) 0.5929(4) 0.4279(2) 0.0219(6) Uani 1 1 d . . . . .
H15 H 0.779082 0.617553 0.485244 0.026 Uiso 1 1 calc R . . . .
C17 C 0.6537(3) 0.5197(4) 0.2508(2) 0.0239(6) Uani 1 1 d . . . . .
H17 H 0.684340 0.493355 0.189440 0.029 Uiso 1 1 calc R . . . .
C16 C 0.7559(3) 0.5548(4) 0.3362(2) 0.0230(6) Uani 1 1 d . . . . .
H16 H 0.855371 0.552910 0.332225 0.028 Uiso 1 1 calc R . . . .
C11 C 0.2598(3) 0.7665(4) 0.3435(2) 0.0187(5) Uani 1 1 d . . . . .
H11A H 0.337819 0.830212 0.384046 0.022 Uiso 1 1 calc R . . . .
H11B H 0.256474 0.797708 0.272552 0.022 Uiso 1 1 calc R . . . .
C13 C 0.4576(3) 0.5598(3) 0.3484(2) 0.0176(5) Uani 1 1 d . . . . .
C21 C 0.1347(3) 0.1914(4) 0.2104(2) 0.0245(6) Uani 1 1 d . . . . .
H21 H 0.151043 0.076219 0.213065 0.029 Uiso 1 1 calc R . . . .
C3 C 0.2180(3) 0.3360(4) 0.9183(2) 0.0257(6) Uani 1 1 d . . . . .
H3 H 0.130182 0.313286 0.941216 0.031 Uiso 1 1 calc R . . . .
C4 C 0.3500(3) 0.2903(4) 0.9784(2) 0.0255(6) Uani 1 1 d . . . . .
H4 H 0.351483 0.236716 1.040765 0.031 Uiso 1 1 calc R . . . .
H1 H 0.192(4) 0.461(4) 0.452(2) 0.028(9) Uiso 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C10 O3 C11 114.85(19) . . ?
C9 N1 C12 114.8(2) . . ?
C6 C1 C7 117.2(2) . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 C7 123.5(2) . . ?
O3 C10 C9 114.0(2) . . ?
O2 C10 O3 119.2(2) . . ?
O2 C10 C9 126.7(2) . . ?
C24 C19 C12 123.5(2) . . ?
C24 C19 C20 118.2(3) . . ?
C20 C19 C12 118.3(2) . . ?
N1 C12 C19 108.4(2) . . ?
N1 C12 C11 108.2(2) . . ?
N1 C12 C13 109.9(2) . . ?
C19 C12 C11 112.9(2) . . ?
C19 C12 C13 111.6(2) . . ?
C13 C12 C11 105.7(2) . . ?
C5 C6 C1 119.8(3) . . ?
O1 C7 C1 119.9(2) . . ?
O1 C7 C8 121.4(2) . . ?
C1 C7 C8 118.7(2) . . ?
N1 C9 C10 109.6(2) . . ?
N1 C9 C8 110.1(2) . . ?
C8 C9 C10 112.6(2) . . ?
C9 C8 C7 111.6(2) . . ?
C23 C22 C21 119.2(3) . . ?
C17 C18 C13 120.7(3) . . ?
C19 C24 C23 120.8(3) . . ?
C15 C14 C13 120.6(3) . . ?
C21 C20 C19 120.8(3) . . ?
C6 C5 Cl1 118.7(2) . . ?
C6 C5 C4 121.7(3) . . ?
C4 C5 Cl1 119.6(2) . . ?
C22 C23 C24 120.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C17 C18 120.0(3) . . ?
C17 C16 C15 120.0(2) . . ?
O3 C11 C12 112.0(2) . . ?
C18 C13 C12 122.1(2) . . ?
C18 C13 C14 118.7(2) . . ?
C14 C13 C12 118.9(2) . . ?
C20 C21 C22 120.4(3) . . ?
C2 C3 C4 121.0(3) . . ?
C5 C4 C3 118.2(3) . . ?
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 C5 1.741(3) . ?
O3 C10 1.359(3) . ?
O3 C11 1.449(3) . ?
O1 C7 1.220(3) . ?
O2 C10 1.201(3) . ?
N1 C12 1.486(3) . ?
N1 C9 1.472(3) . ?
C1 C6 1.397(4) . ?
C1 C7 1.489(4) . ?
C1 C2 1.395(4) . ?
C10 C9 1.519(4) . ?
C19 C12 1.529(4) . ?
C19 C24 1.391(4) . ?
C19 C20 1.399(4) . ?
C12 C11 1.540(4) . ?
C12 C13 1.539(3) . ?
C6 C5 1.375(4) . ?
C7 C8 1.515(4) . ?
C9 C8 1.513(4) . ?
C22 C23 1.381(4) . ?
C22 C21 1.389(4) . ?
C18 C17 1.389(4) . ?
C18 C13 1.392(4) . ?
C24 C23 1.393(4) . ?
C14 C15 1.388(4) . ?
C14 C13 1.393(4) . ?
C20 C21 1.388(4) . ?
C5 C4 1.388(4) . ?
C2 C3 1.386(4) . ?
C15 C16 1.385(4) . ?
C17 C16 1.381(4) . ?
C3 C4 1.393(4) . ?
