#------------------------------------------------------------------------------
#$Date: 2022-08-27 01:37:51 +0300 (Sat, 27 Aug 2022) $
#$Revision: 277414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567530.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_1567530
loop_
_publ_author_name
'Gonzálvez, Miguel A.'
'Su, Chuyi'
'Williams, Craig M.'
'Bernhardt, Paul V.'
_publ_section_title
;
 Organocopper(ii) complexes: new catalysts for carbon--carbon bond
 formation via electrochemical atom transfer radical addition (eATRA)
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03418B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 Cl N'
_chemical_formula_weight         229.7
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_creation_date             2022-05-30T14:31:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-06-01 deposited with the CCDC.	2022-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6527(6)
_cell_length_b                   16.6170(8)
_cell_length_c                   5.9865(4)
_cell_measurement_reflns_used    813
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      60.88
_cell_measurement_theta_min      4.62
_cell_measurement_wavelength     1.54184
_cell_volume                     1159.18(11)
_computing_cell_refinement       'CrysalisPro (Agilent Technologies,     )'
_computing_data_collection       'CrysalisPro (Agilent Technologies,     )'
_computing_data_reduction        'CrysalisPro (Agilent Technologies,     )'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, EosS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.071392
_diffrn_orient_matrix_UB_12      -0.073053
_diffrn_orient_matrix_UB_13      0.076406
_diffrn_orient_matrix_UB_21      -0.109941
_diffrn_orient_matrix_UB_22      0.051402
_diffrn_orient_matrix_UB_23      -0.011069
_diffrn_orient_matrix_UB_31      -0.017039
_diffrn_orient_matrix_UB_32      -0.025015
_diffrn_orient_matrix_UB_33      -0.245371
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2672
_diffrn_reflns_point_group_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        61.428
_diffrn_reflns_theta_max         61.428
_diffrn_reflns_theta_min         4.635
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.65
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: petroleum ether'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0616P)²+0.4844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.423
_reflns_Friedel_fraction_full    0.525
_reflns_Friedel_fraction_max     0.525
_reflns_number_gt                1206
_reflns_number_total             1403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03418b2.cif
_cod_data_source_block           2130lesley2
_cod_database_code               1567530
_shelx_shelxl_version_number     2018/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
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 0.7647(5) 0.4393(3) 0.2318(10) 0.0419(14) Uani 1 1 d . . . . .
H1 H 0.837523 0.447991 0.164901 0.05 Uiso 1 1 calc R U . . .
C2 C 0.7396(5) 0.4732(3) 0.4400(11) 0.0423(15) Uani 1 1 d . . . . .
H2 H 0.795953 0.504719 0.514196 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6352(4) 0.4617(3) 0.5378(10) 0.0369(13) Uani 1 1 d . . . . .
H3 H 0.619515 0.485428 0.678876 0.044 Uiso 1 1 calc R U . . .
C4 C 0.5500(4) 0.4148(3) 0.4314(9) 0.0311(12) Uani 1 1 d . . . . .
C5 C 0.5746(4) 0.3795(3) 0.2211(9) 0.0337(12) Uani 1 1 d . . . . .
C6 C 0.6843(4) 0.3936(3) 0.1250(12) 0.0408(13) Uani 1 1 d . . . . .
H6 H 0.702057 0.370722 -0.016261 0.049 Uiso 1 1 calc R U . . .
C7 C 0.4413(4) 0.4017(3) 0.5302(10) 0.0326(12) Uani 1 1 d . . . . .
H7 H 0.424438 0.425612 0.670465 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3607(5) 0.3556(3) 0.4287(10) 0.0357(13) Uani 1 1 d . . . . .
C9 C 0.3851(5) 0.3196(3) 0.2219(11) 0.0439(15) Uani 1 1 d . . . . .
H9 H 0.329043 0.286717 0.15154 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4892(4) 0.3315(3) 0.1212(12) 0.0411(13) Uani 1 1 d . . . . .
H10 H 0.50411 0.306896 -0.019081 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2465(4) 0.3435(3) 0.5442(10) 0.0397(14) Uani 1 1 d . . . . .
H11 H 0.243849 0.379346 0.678325 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1440(5) 0.3622(4) 0.3990(11) 0.0467(15) Uani 1 1 d . . . . .
H12A H 0.150145 0.330121 0.26014 0.056 Uiso 1 1 calc R U . . .
H12B H 0.147422 0.419697 0.356239 0.056 Uiso 1 1 calc R U . . .
C13 C 0.0270(5) 0.3458(4) 0.5039(13) 0.0559(18) Uani 1 1 d . . . . .
H13A H -0.033814 0.363609 0.399435 0.067 Uiso 1 1 calc R U . . .
H13B H 0.018044 0.287145 0.526589 0.067 Uiso 1 1 calc R U . . .
C14 C 0.0112(5) 0.3871(4) 0.7193(15) 0.0546(18) Uani 1 1 d . . . . .
Cl1 Cl 0.24010(12) 0.23944(7) 0.6387(4) 0.0583(5) Uani 1 1 d . . . . .
N1 N 0.0015(5) 0.4184(5) 0.8842(15) 0.080(2) 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 0 '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 0.018 '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
C6 C1 C2 119.9(5) . . ?
C3 C2 C1 120.8(6) . . ?
C2 C3 C4 120.7(6) . . ?
C3 C4 C7 121.7(5) . . ?
C3 C4 C5 119.1(5) . . ?
C7 C4 C5 119.2(5) . . ?
C10 C5 C4 117.9(5) . . ?
C10 C5 C6 123.9(5) . . ?
C4 C5 C6 118.2(5) . . ?
C1 C6 C5 121.3(6) . . ?
C8 C7 C4 121.3(5) . . ?
C7 C8 C9 119.7(5) . . ?
C7 C8 C11 118.6(5) . . ?
C9 C8 C11 121.6(5) . . ?
C10 C9 C8 120.4(5) . . ?
C9 C10 C5 121.4(6) . . ?
C12 C11 C8 113.9(5) . . ?
C12 C11 Cl1 110.0(4) . . ?
C8 C11 Cl1 107.7(3) . . ?
C11 C12 C13 115.7(6) . . ?
C14 C13 C12 112.9(6) . . ?
N1 C14 C13 178.6(7) . . ?
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 C6 1.364(8) . ?
C1 C2 1.399(9) . ?
C2 C3 1.363(8) . ?
C3 C4 1.413(8) . ?
C4 C7 1.415(7) . ?
C4 C5 1.419(8) . ?
C5 C10 1.408(8) . ?
C5 C6 1.422(7) . ?
C7 C8 1.355(8) . ?
C8 C9 1.404(9) . ?
C8 C11 1.514(7) . ?
C9 C10 1.369(8) . ?
C11 C12 1.510(8) . ?
C11 Cl1 1.821(5) . ?
C12 C13 1.526(8) . ?
C13 C14 1.472(11) . ?
C14 N1 1.122(10) . ?
