#------------------------------------------------------------------------------
#$Date: 2022-08-27 01:37:51 +0300 (Sat, 27 Aug 2022) $
#$Revision: 277414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567527.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_1567527
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 Br N'
_chemical_formula_weight         274.16
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_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             2022-05-30T14:50:26-00:00
_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                   11.5971(6)
_cell_length_b                   17.1790(10)
_cell_length_c                   5.9922(3)
_cell_measurement_reflns_used    1171
_cell_measurement_temperature    194(2)
_cell_measurement_theta_max      61.34
_cell_measurement_theta_min      4.6
_cell_measurement_wavelength     1.54184
_cell_volume                     1193.81(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)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      194(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.02
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      0.091467
_diffrn_orient_matrix_UB_12      0.064391
_diffrn_orient_matrix_UB_13      0.026688
_diffrn_orient_matrix_UB_21      -0.090944
_diffrn_orient_matrix_UB_22      0.061894
_diffrn_orient_matrix_UB_23      -0.060112
_diffrn_orient_matrix_UB_31      -0.031806
_diffrn_orient_matrix_UB_32      0.008157
_diffrn_orient_matrix_UB_33      0.248495
_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     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2736
_diffrn_reflns_point_group_measured_fraction_full 0.745
_diffrn_reflns_point_group_measured_fraction_max 0.745
_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        61.486
_diffrn_reflns_theta_max         61.486
_diffrn_reflns_theta_min         4.6
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.436
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.881
_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    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate and petroleum ether'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.27
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1382
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0342
_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)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.346
_reflns_Friedel_fraction_full    0.43
_reflns_Friedel_fraction_max     0.43
_reflns_number_gt                1246
_reflns_number_total             1382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03418b2.cif
_cod_data_source_block           2214mg14
_cod_database_code               1567527
_shelx_estimated_absorpt_t_min   0.471
_shelx_estimated_absorpt_t_max   0.917
_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 0.7673(5) 0.4442(4) 0.2398(10) 0.0364(14) Uani 1 1 d . . . . .
H1 H 0.839889 0.453798 0.171549 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7422(5) 0.4769(4) 0.4493(10) 0.0363(14) Uani 1 1 d . . . . .
H2 H 0.798408 0.507542 0.523833 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6370(4) 0.4645(3) 0.5460(10) 0.0338(12) Uani 1 1 d . . . . .
H3 H 0.62057 0.487304 0.686888 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5532(4) 0.4189(3) 0.4411(9) 0.0278(12) Uani 1 1 d . . . . .
C5 C 0.5780(5) 0.3845(3) 0.2293(8) 0.0292(13) Uani 1 1 d . . . . .
C6 C 0.6882(4) 0.3992(3) 0.1350(13) 0.0361(12) Uani 1 1 d . . . . .
H6 H 0.707005 0.376763 -0.005335 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4430(4) 0.4043(3) 0.5378(10) 0.0309(12) Uani 1 1 d . . . . .
H7 H 0.425212 0.426571 0.678686 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3627(5) 0.3594(3) 0.4346(9) 0.0301(12) Uani 1 1 d . . . . .
C9 C 0.3897(5) 0.3248(3) 0.2258(9) 0.0366(14) Uani 1 1 d . . . . .
H9 H 0.334319 0.29282 0.153459 0.044 Uiso 1 1 calc R U . . .
C10 C 0.4939(4) 0.3370(3) 0.1288(12) 0.0373(14) Uani 1 1 d . . . . .
H10 H 0.510512 0.31281 -0.010151 0.045 Uiso 1 1 calc R U . . .
C11 C 0.2469(4) 0.3469(3) 0.5454(10) 0.0309(12) Uani 1 1 d . . . . .
H11 H 0.242528 0.382082 0.678015 0.037 Uiso 1 1 calc R U . . .
C12 C 0.1447(5) 0.3636(5) 0.3992(11) 0.0498(17) Uani 1 1 d . . . . .
H12A H 0.152541 0.332749 0.260578 0.06 Uiso 1 1 calc R U . . .
H12B H 0.14703 0.419303 0.356597 0.06 Uiso 1 1 calc R U . . .
C13 C 0.0263(6) 0.3465(5) 0.5008(13) 0.0550(19) Uani 1 1 d . . . . .
H13A H -0.034501 0.362952 0.394943 0.066 Uiso 1 1 calc R U . . .
H13B H 0.018486 0.289712 0.524467 0.066 Uiso 1 1 calc R U . . .
C14 C 0.0097(5) 0.3869(5) 0.7139(14) 0.057(2) Uani 1 1 d . . . . .
Br1 Br 0.24166(5) 0.23796(3) 0.6542(3) 0.0514(3) Uani 1 1 d . . . . .
N1 N -0.0008(5) 0.4179(6) 0.8772(16) 0.083(3) 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'
Br Br -0.6763 1.2805 '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 120.1(5) . . ?
C3 C2 C1 120.1(6) . . ?
C2 C3 C4 121.1(6) . . ?
C3 C4 C7 122.6(5) . . ?
C3 C4 C5 119.4(5) . . ?
C7 C4 C5 118.0(5) . . ?
C10 C5 C6 123.8(5) . . ?
C10 C5 C4 118.7(5) . . ?
C6 C5 C4 117.5(5) . . ?
C1 C6 C5 121.7(6) . . ?
C8 C7 C4 122.0(5) . . ?
C7 C8 C9 119.2(5) . . ?
C7 C8 C11 119.3(5) . . ?
C9 C8 C11 121.5(5) . . ?
C10 C9 C8 120.6(6) . . ?
C9 C10 C5 121.5(6) . . ?
C12 C11 C8 114.7(5) . . ?
C12 C11 Br1 110.4(4) . . ?
C8 C11 Br1 107.8(4) . . ?
C11 C12 C13 116.0(5) . . ?
C14 C13 C12 112.0(7) . . ?
N1 C14 C13 178.7(8) . . ?
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 1.355(9) . ?
C1 C2 1.405(9) . ?
C2 C3 1.367(8) . ?
C3 C4 1.398(8) . ?
C4 C7 1.425(8) . ?
C4 C5 1.429(8) . ?
C5 C10 1.407(8) . ?
C5 C6 1.420(8) . ?
C7 C8 1.357(8) . ?
C8 C9 1.420(8) . ?
C8 C11 1.513(7) . ?
C9 C10 1.358(8) . ?
C11 C12 1.502(8) . ?
C11 Br1 1.983(5) . ?
C12 C13 1.530(10) . ?
C13 C14 1.466(12) . ?
C14 N1 1.121(11) . ?
