#------------------------------------------------------------------------------
#$Date: 2021-08-26 01:11:19 +0300 (Thu, 26 Aug 2021) $
#$Revision: 268205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564398.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_1564398
loop_
_publ_author_name
'Wu, Xiao-Feng'
'Yuan, Yang'
'Zhao, Fengqian'
_publ_section_title
;
 Copper-Catalyzed Enantioselective Carbonylation Toward α-Chiral
 Secondary Amides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04210F
_journal_year                    2021
_chemical_formula_sum            'C21 H33 N O'
_chemical_formula_weight         315.48
_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_method           SHELXL-2018/3
_audit_update_record
;
2021-05-18 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.2538(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.08320(10)
_cell_length_b                   22.6617(7)
_cell_length_c                   8.1122(2)
_cell_measurement_reflns_used    4415
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      3.90
_cell_volume                     909.59(4)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         microfocus
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.610
_diffrn_reflns_theta_max         66.610
_diffrn_reflns_theta_min         3.901
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       'part of a needle'
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0329
_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)+(0.0563P)²+0.0353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0847
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3079
_reflns_number_total             3203
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc04210f2.cif
_cod_data_source_block           AX2108
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1564398
_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.
;
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
C1 C 0.5716(4) 0.63914(9) 0.9726(2) 0.0260(4) Uani 1 1 d . . . . .
C2 C 0.7135(4) 0.57994(9) 1.0249(3) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.886348 0.579717 0.985810 0.030 Uiso 1 1 calc R U . . .
C3 C 0.5368(5) 0.52963(10) 0.9351(3) 0.0316(5) Uani 1 1 d . . . . .
H3A H 0.624514 0.491771 0.971076 0.047 Uiso 1 1 calc R U . . .
H3B H 0.512447 0.533950 0.812283 0.047 Uiso 1 1 calc R U . . .
H3C H 0.360194 0.530913 0.964255 0.047 Uiso 1 1 calc R U . . .
C4 C 0.7837(4) 0.57526(8) 1.2173(3) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.6280(4) 0.54270(9) 1.3051(3) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.471492 0.522653 1.244301 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6989(5) 0.53923(10) 1.4802(3) 0.0304(5) Uani 1 1 d . . . . .
H6 H 0.591470 0.516545 1.538292 0.036 Uiso 1 1 calc R U . . .
C7 C 0.9251(5) 0.56853(10) 1.5714(3) 0.0321(5) Uani 1 1 d . . . . .
H7 H 0.972955 0.566173 1.691543 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0806(5) 0.60133(10) 1.4851(3) 0.0337(5) Uani 1 1 d . . . . .
H8 H 1.235639 0.621680 1.546547 0.040 Uiso 1 1 calc R U . . .
C9 C 1.0117(5) 0.60467(10) 1.3101(3) 0.0300(5) Uani 1 1 d . . . . .
H9 H 1.120487 0.627171 1.252494 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6261(4) 0.74125(10) 0.8866(3) 0.0264(4) Uani 1 1 d . . . . .
H10 H 0.494891 0.751278 0.957240 0.032 Uiso 1 1 calc R U . . .
C11 C 0.8576(4) 0.78618(9) 0.9289(3) 0.0266(4) Uani 1 1 d . . . . .
H11A H 0.975565 0.781379 0.848196 0.032 Uiso 1 1 calc R U . . .
H11B H 0.967805 0.778189 1.044150 0.032 Uiso 1 1 calc R U . . .
C12 C 0.7536(4) 0.84999(9) 0.9205(3) 0.0285(4) Uani 1 1 d . . . . .
H12A H 0.604066 0.854270 0.818857 0.034 Uiso 1 1 calc R U . . .
H12B H 0.678856 0.857569 1.020980 0.034 Uiso 1 1 calc R U . . .
C13 C 0.9686(4) 0.89689(10) 0.9138(3) 0.0302(5) Uani 1 1 d . . . . .
H13A H 0.897499 0.936138 0.935189 0.036 Uiso 1 1 calc R U . . .
H13B H 1.130466 0.889006 1.005354 0.036 Uiso 1 1 calc R U . . .
C14 C 1.0518(4) 0.89838(9) 0.7443(3) 0.0292(4) Uani 1 1 d . . . . .
H14A H 1.100510 0.857885 0.716456 0.035 Uiso 1 1 calc R U . . .
H14B H 1.215316 0.923230 0.756694 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8331(4) 0.92215(10) 0.5956(3) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.653583 0.909449 0.610400 0.037 Uiso 1 1 calc R U . . .
H15B H 0.837522 0.965817 0.598387 0.037 Uiso 1 1 calc R U . . .
C16 C 0.8678(5) 0.90118(10) 0.4225(3) 0.0335(5) Uani 1 1 d . . . . .
H16A H 1.051377 0.911980 0.410788 0.040 Uiso 1 1 calc R U . . .
H16B H 0.736372 0.922375 0.333165 0.040 Uiso 1 1 calc R U . . .
C17 C 0.8283(5) 0.83464(11) 0.3930(3) 0.0318(5) Uani 1 1 d . . . . .
H17A H 0.889882 0.823897 0.289649 0.038 Uiso 1 1 calc R U . . .
H17B H 0.945135 0.813532 0.489407 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5378(5) 0.81313(11) 0.3733(3) 0.0327(5) Uani 1 1 d . . . . .
H18A H 0.431014 0.825053 0.260303 0.039 Uiso 1 1 calc R U . . .
H18B H 0.458549 0.832959 0.459311 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5123(5) 0.74638(11) 0.3921(3) 0.0334(5) Uani 1 1 d . . . . .
H19A H 0.604764 0.726494 0.312486 0.040 Uiso 1 1 calc R U . . .
H19B H 0.318709 0.735501 0.359400 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6313(4) 0.72343(10) 0.5714(3) 0.0294(4) Uani 1 1 d . . . . .
H20A H 0.637735 0.679787 0.568393 0.035 Uiso 1 1 calc R U . . .
H20B H 0.819186 0.737945 0.609172 0.035 Uiso 1 1 calc R U . . .
C21 C 0.4703(4) 0.74244(10) 0.7002(3) 0.0266(4) Uani 1 1 d . . . . .
H21A H 0.310767 0.716348 0.687639 0.032 Uiso 1 1 calc R U . . .
H21B H 0.403028 0.783054 0.672105 0.032 Uiso 1 1 calc R U . . .
N1 N 0.7300(4) 0.68206(8) 0.9357(2) 0.0266(4) Uani 1 1 d . . . . .
H1 H 0.895(7) 0.6751(14) 0.940(4) 0.036(7) Uiso 1 1 d . . . . .
O1 O 0.3302(3) 0.64611(7) 0.9680(2) 0.0322(4) Uani 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 0.0181 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
O1 C1 N1 123.15(19) . . ?
O1 C1 C2 121.54(19) . . ?
N1 C1 C2 115.30(17) . . ?
C4 C2 C3 114.23(18) . . ?
C4 C2 C1 109.17(16) . . ?
C3 C2 C1 109.41(18) . . ?
C4 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C9 118.41(19) . . ?
C5 C4 C2 122.31(19) . . ?
C9 C4 C2 119.29(18) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
N1 C10 C11 109.69(17) . . ?
N1 C10 C21 110.87(18) . . ?
C11 C10 C21 113.82(17) . . ?
N1 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C21 C10 H10 107.4 . . ?
C10 C11 C12 112.10(17) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 114.40(18) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 113.14(18) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 114.44(19) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.33(19) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 114.21(18) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 114.76(19) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 114.03(19) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 C20 113.98(18) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 113.34(18) . . ?
C21 C20 H20A 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C10 115.56(17) . . ?
C20 C21 H21A 108.4 . . ?
C10 C21 H21A 108.4 . . ?
C20 C21 H21B 108.4 . . ?
C10 C21 H21B 108.4 . . ?
H21A C21 H21B 107.5 . . ?
C1 N1 C10 121.91(18) . . ?
C1 N1 H1 120(2) . . ?
C10 N1 H1 118(2) . . ?
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
C1 O1 1.229(3) . ?
C1 N1 1.340(3) . ?
C1 C2 1.536(3) . ?
C2 C4 1.523(3) . ?
C2 C3 1.529(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.391(3) . ?
C4 C9 1.398(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 N1 1.463(3) . ?
C10 C11 1.535(3) . ?
C10 C21 1.538(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.536(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.534(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.538(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.531(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.533(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.528(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.529(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.532(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.529(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
N1 H1 0.85(4) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C4 -80.4(3) . . . . ?
N1 C1 C2 C4 98.6(2) . . . . ?
O1 C1 C2 C3 45.3(3) . . . . ?
N1 C1 C2 C3 -135.71(19) . . . . ?
C3 C2 C4 C5 -22.6(3) . . . . ?
C1 C2 C4 C5 100.3(2) . . . . ?
C3 C2 C4 C9 157.6(2) . . . . ?
C1 C2 C4 C9 -79.6(2) . . . . ?
C9 C4 C5 C6 -0.5(3) . . . . ?
C2 C4 C5 C6 179.68(19) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 0.3(3) . . . . ?
C5 C4 C9 C8 0.1(3) . . . . ?
C2 C4 C9 C8 179.9(2) . . . . ?
N1 C10 C11 C12 -166.35(16) . . . . ?
C21 C10 C11 C12 68.8(2) . . . . ?
C10 C11 C12 C13 -164.31(18) . . . . ?
C11 C12 C13 C14 71.5(2) . . . . ?
C12 C13 C14 C15 70.1(2) . . . . ?
C13 C14 C15 C16 -156.81(19) . . . . ?
C14 C15 C16 C17 66.1(3) . . . . ?
C15 C16 C17 C18 69.6(3) . . . . ?
C16 C17 C18 C19 -164.28(18) . . . . ?
C17 C18 C19 C20 67.6(3) . . . . ?
C18 C19 C20 C21 69.0(3) . . . . ?
C19 C20 C21 C10 -158.45(19) . . . . ?
N1 C10 C21 C20 -58.4(2) . . . . ?
C11 C10 C21 C20 65.9(2) . . . . ?
O1 C1 N1 C10 0.0(3) . . . . ?
C2 C1 N1 C10 -178.95(17) . . . . ?
C11 C10 N1 C1 154.79(19) . . . . ?
C21 C10 N1 C1 -78.7(2) . . . . ?
