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#$Date: 2020-10-04 06:25:54 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/50/4135014.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_4135014
loop_
_publ_author_name
'Qiu, Hui'
'Shuai, Bin'
'Wang, Yun-Zhao'
'Liu, Dong'
'Chen, Yue-Gang'
'Gao, Pei-Sen'
'Ma, Hong-Xing'
'Chen, Song'
'Mei, Tian-Sheng'
_publ_section_title
;
 Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl
 Atropisomers.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9872
_journal_page_last               9878
_journal_paper_doi               10.1021/jacs.9b13117
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H16 N2 O'
_chemical_formula_weight         264.32
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 103.8900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.3490(3)
_cell_length_b                   8.6180(4)
_cell_length_c                   13.1236(6)
_cell_measurement_reflns_used    8884
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.174
_cell_measurement_theta_min      10.263
_cell_volume                     697.07(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9842
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.474
_diffrn_reflns_theta_min         8.711
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.019
_refine_ls_abs_structure_details
; 
 Flack x determined using 1075 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_coef       0.098(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0287
_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)+(0.0363P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                2379
_reflns_number_total             2399
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b13117_si_006.cif
_cod_data_source_block           cu_d8v19673_0m
_cod_depositor_comments
;Adding full bibliography for 4135012--4135016.cif.

 Adding full bibliography for 4135012--4135016.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4135014
_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_min   0.895
_shelx_estimated_absorpt_t_max   0.917
_shelxl_version_number           2013-4
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 0.4932(2) 0.39864(17) 0.13416(10) 0.0512(4) Uani 1 1 d . . . . .
N1 N 0.2084(2) 0.36391(18) 0.20724(12) 0.0420(4) Uani 1 1 d . . . . .
N2 N 0.4810(2) 0.19463(17) 0.37216(12) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.1003(3) 0.6289(2) 0.14441(14) 0.0420(4) Uani 1 1 d . . . . .
C2 C -0.0331(3) 0.6859(3) 0.20495(16) 0.0524(5) Uani 1 1 d . . . . .
H2 H -0.1267 0.6200 0.2290 0.063 Uiso 1 1 calc R U . . .
C3 C -0.0254(4) 0.8422(3) 0.22918(18) 0.0638(6) Uani 1 1 d . . . . .
H3 H -0.1148 0.8821 0.2695 0.077 Uiso 1 1 calc R U . . .
C4 C 0.1153(4) 0.9396(3) 0.19359(19) 0.0645(6) Uani 1 1 d . . . . .
H4 H 0.1206 1.0444 0.2108 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2471(4) 0.8828(3) 0.13314(18) 0.0587(6) Uani 1 1 d . . . . .
H5 H 0.3410 0.9489 0.1095 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2393(3) 0.7262(2) 0.10754(14) 0.0475(5) Uani 1 1 d . . . . .
C7 C 0.3621(4) 0.6389(3) 0.04085(18) 0.0598(6) Uani 1 1 d . . . . .
H7A H 0.5164 0.6598 0.0633 0.072 Uiso 1 1 calc R U . . .
H7B H 0.3114 0.6671 -0.0325 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3143(3) 0.4688(3) 0.05790(14) 0.0511(5) Uani 1 1 d . . . . .
H8 H 0.2797 0.4109 -0.0083 0.061 Uiso 1 1 calc R U . . .
C9 C 0.1270(3) 0.4623(2) 0.11408(14) 0.0438(4) Uani 1 1 d . . . . .
H9 H -0.0064 0.4206 0.0685 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4063(3) 0.34015(19) 0.21205(13) 0.0378(4) Uani 1 1 d . . . . .
C11 C 0.5637(3) 0.26025(19) 0.29733(13) 0.0366(4) Uani 1 1 d . . . . .
C12 C 0.7830(3) 0.2615(2) 0.30024(15) 0.0467(5) Uani 1 1 d . . . . .
H12 H 0.8338 0.3069 0.2464 0.056 Uiso 1 1 calc R U . . .
C13 C 0.9243(3) 0.1938(3) 0.38486(17) 0.0546(5) Uani 1 1 d . . . . .
H13 H 1.0727 0.1930 0.3894 0.066 Uiso 1 1 calc R U . . .
C14 C 0.8422(3) 0.1277(3) 0.46244(17) 0.0542(5) Uani 1 1 d . . . . .
H14 H 0.9349 0.0823 0.5205 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6187(3) 0.1291(2) 0.45342(15) 0.0435(4) Uani 1 1 d . . . . .
C16 C 0.5219(4) 0.0614(3) 0.53744(17) 0.0563(5) Uani 1 1 d . . . . .
H16A H 0.6270 -0.0074 0.5811 0.068 Uiso 1 1 calc R U . . .
H16B H 0.3958 0.0000 0.5047 0.068 Uiso 1 1 calc R U . . .
C17 C 0.4556(4) 0.1836(3) 0.60576(17) 0.0637(6) Uani 1 1 d . . . . .
H17A H 0.3473 0.2496 0.5634 0.096 Uiso 1 1 calc R U . . .
H17B H 0.5799 0.2445 0.6387 0.096 Uiso 1 1 calc R U . . .
H17C H 0.3973 0.1344 0.6587 0.096 Uiso 1 1 calc R U . . .
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
C10 O1 C8 106.19(14) . . ?
C10 N1 C9 106.38(14) . . ?
C15 N2 C11 117.86(14) . . ?
C2 C1 C6 121.02(17) . . ?
C2 C1 C9 127.71(17) . . ?
C6 C1 C9 111.20(16) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.7(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 C7 111.28(17) . . ?
C5 C6 C7 129.25(19) . . ?
C6 C7 C8 104.25(16) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C7 110.55(18) . . ?
O1 C8 C9 102.73(14) . . ?
C7 C8 C9 107.98(17) . . ?
O1 C8 H8 111.7 . . ?
C7 C8 H8 111.7 . . ?
C9 C8 H8 111.7 . . ?
N1 C9 C1 111.54(14) . . ?
N1 C9 C8 105.06(14) . . ?
C1 C9 C8 103.83(15) . . ?
N1 C9 H9 112.0 . . ?
C1 C9 H9 112.0 . . ?
C8 C9 H9 112.0 . . ?
N1 C10 O1 118.60(16) . . ?
N1 C10 C11 126.73(15) . . ?
O1 C10 C11 114.60(14) . . ?
N2 C11 C12 123.35(16) . . ?
N2 C11 C10 115.94(14) . . ?
C12 C11 C10 120.65(15) . . ?
C13 C12 C11 118.36(17) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 118.90(17) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 119.49(18) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N2 C15 C14 122.03(17) . . ?
N2 C15 C16 116.55(16) . . ?
C14 C15 C16 121.39(18) . . ?
C15 C16 C17 112.77(19) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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 C10 1.369(2) . ?
O1 C8 1.453(2) . ?
N1 C10 1.260(2) . ?
N1 C9 1.476(2) . ?
N2 C15 1.331(2) . ?
N2 C11 1.344(2) . ?
C1 C2 1.383(3) . ?
C1 C6 1.386(3) . ?
C1 C9 1.511(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(3) . ?
C7 C8 1.524(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.544(3) . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C10 C11 1.479(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.503(3) . ?
C16 C17 1.507(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C6 C1 C2 C3 -0.4(3) . . . . ?
C9 C1 C2 C3 176.25(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C9 C1 C6 C5 -176.21(17) . . . . ?
C2 C1 C6 C7 -178.14(17) . . . . ?
C9 C1 C6 C7 4.7(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C1 C6 C7 C8 -10.5(2) . . . . ?
C5 C6 C7 C8 170.44(19) . . . . ?
C10 O1 C8 C7 123.47(16) . . . . ?
C10 O1 C8 C9 8.46(19) . . . . ?
C6 C7 C8 O1 -99.47(18) . . . . ?
C6 C7 C8 C9 12.2(2) . . . . ?
C10 N1 C9 C1 -103.71(18) . . . . ?
C10 N1 C9 C8 8.15(18) . . . . ?
C2 C1 C9 N1 -61.1(2) . . . . ?
C6 C1 C9 N1 115.83(16) . . . . ?
C2 C1 C9 C8 -173.75(17) . . . . ?
C6 C1 C9 C8 3.20(19) . . . . ?
O1 C8 C9 N1 -10.04(19) . . . . ?
C7 C8 C9 N1 -126.89(16) . . . . ?
O1 C8 C9 C1 107.20(16) . . . . ?
C7 C8 C9 C1 -9.7(2) . . . . ?
C9 N1 C10 O1 -3.0(2) . . . . ?
C9 N1 C10 C11 173.81(16) . . . . ?
C8 O1 C10 N1 -4.0(2) . . . . ?
C8 O1 C10 C11 178.88(15) . . . . ?
C15 N2 C11 C12 0.7(3) . . . . ?
C15 N2 C11 C10 -176.30(15) . . . . ?
N1 C10 C11 N2 6.4(2) . . . . ?
O1 C10 C11 N2 -176.69(14) . . . . ?
N1 C10 C11 C12 -170.63(18) . . . . ?
O1 C10 C11 C12 6.3(2) . . . . ?
N2 C11 C12 C13 -0.9(3) . . . . ?
C10 C11 C12 C13 175.94(18) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
C11 N2 C15 C14 0.2(3) . . . . ?
C11 N2 C15 C16 178.06(16) . . . . ?
C13 C14 C15 N2 -0.8(3) . . . . ?
C13 C14 C15 C16 -178.6(2) . . . . ?
N2 C15 C16 C17 -74.8(2) . . . . ?
C14 C15 C16 C17 103.1(2) . . . . ?
