#------------------------------------------------------------------------------
#$Date: 2022-08-27 01:37:51 +0300 (Sat, 27 Aug 2022) $
#$Revision: 277414 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/75/1567526.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_1567526
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_formula_sum            'C28 H36 N2'
_chemical_formula_weight         400.59
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_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             2022-05-30T15:54:19-00:00
_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                73.723(11)
_cell_angle_beta                 77.522(10)
_cell_angle_gamma                79.838(8)
_cell_formula_units_Z            1
_cell_length_a                   6.2887(6)
_cell_length_b                   9.7101(10)
_cell_length_c                   10.8010(14)
_cell_measurement_reflns_used    520
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      59.73
_cell_measurement_theta_min      4.78
_cell_measurement_wavelength     1.54184
_cell_volume                     613.42(12)
_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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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      0.04854
_diffrn_orient_matrix_UB_12      0.058324
_diffrn_orient_matrix_UB_13      -0.150052
_diffrn_orient_matrix_UB_21      -0.05242
_diffrn_orient_matrix_UB_22      0.156011
_diffrn_orient_matrix_UB_23      0.015469
_diffrn_orient_matrix_UB_31      0.242536
_diffrn_orient_matrix_UB_32      0.000579
_diffrn_orient_matrix_UB_33      0.005625
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3087
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_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        61.543
_diffrn_reflns_theta_max         61.543
_diffrn_reflns_theta_min         4.332
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             218
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and ethyl acetate'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.813
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     137
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0502
_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)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0
_reflns_number_gt                1672
_reflns_number_total             3087
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc03418b2.cif
_cod_data_source_block           2118mg16
_cod_database_code               1567526
_shelx_shelxl_version_number     2018/1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C3 C 0.4850(4) 0.3701(3) 0.1737(2) 0.0366(7) Uani 1 1 d . . . . .
C11 C 0.5643(4) 0.4262(3) 0.0279(2) 0.0368(6) Uani 1 1 d . . . . .
H11 H 0.721111 0.441906 0.016117 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3359(5) 0.2683(3) 0.4478(3) 0.0387(7) Uani 1 1 d . . . . .
N1 N 1.0742(5) 0.1640(3) 0.0223(3) 0.0660(8) Uani 1 1 d . . . . .
C4 C 0.2832(5) 0.3189(3) 0.2228(3) 0.0476(8) Uani 1 1 d . . . . .
H4 H 0.191546 0.318347 0.16361 0.057 Uiso 1 1 calc R U . . .
C12 C 0.5585(5) 0.3172(3) -0.0485(3) 0.0444(7) Uani 1 1 d . . . . .
H12A H 0.629756 0.353897 -0.140426 0.053 Uiso 1 1 calc R U . . .
H12B H 0.403316 0.310631 -0.048932 0.053 Uiso 1 1 calc R U . . .
C5 C 0.2124(5) 0.2686(3) 0.3561(3) 0.0481(8) Uani 1 1 d . . . . .
H5 H 0.074034 0.233075 0.385745 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6711(4) 0.1646(3) 0.0052(3) 0.0499(8) Uani 1 1 d . . . . .
H13A H 0.588311 0.121873 0.092633 0.06 Uiso 1 1 calc R U . . .
H13B H 0.667426 0.103258 -0.053512 0.06 Uiso 1 1 calc R U . . .
C2 C 0.6090(5) 0.3696(3) 0.2654(3) 0.0497(8) Uani 1 1 d . . . . .
H2 H 0.74803 0.404282 0.235906 0.06 Uiso 1 1 calc R U . . .
C7 C 0.2519(5) 0.2154(3) 0.5947(3) 0.0476(8) Uani 1 1 d . . . . .
C1 C 0.5366(5) 0.3201(4) 0.3983(3) 0.0527(8) Uani 1 1 d . . . . .
H1 H 0.627405 0.321718 0.457614 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8932(6) 0.1645(3) 0.0158(3) 0.0506(8) Uani 1 1 d . . . . .
C8 C 0.4312(6) 0.1872(5) 0.6752(3) 0.0888(14) Uani 1 1 d . . . . .
H8A H 0.499687 0.275461 0.657669 0.133 Uiso 1 1 calc R U . . .
H8B H 0.368116 0.157888 0.768559 0.133 Uiso 1 1 calc R U . . .
H8C H 0.54213 0.109829 0.651719 0.133 Uiso 1 1 calc R U . . .
C9 C 0.0751(6) 0.3326(5) 0.6364(3) 0.0964(15) Uani 1 1 d . . . . .
H9A H -0.042028 0.351674 0.584673 0.145 Uiso 1 1 calc R U . . .
H9B H 0.013857 0.299443 0.729606 0.145 Uiso 1 1 calc R U . . .
H9C H 0.140683 0.421527 0.621433 0.145 Uiso 1 1 calc R U . . .
C10 C 0.1499(8) 0.0763(5) 0.6246(4) 0.1016(16) Uani 1 1 d . . . . .
H10A H 0.032799 0.091867 0.573406 0.152 Uiso 1 1 calc R U . . .
H10B H 0.262573 -0.000315 0.60137 0.152 Uiso 1 1 calc R U . . .
H10C H 0.08856 0.047745 0.71821 0.152 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 0 '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
C2 C3 C4 116.3(2) . . ?
C2 C3 C11 121.7(2) . . ?
C4 C3 C11 122.0(2) . . ?
C3 C11 C12 112.2(2) . . ?
C3 C11 C11 111.5(3) . 2_665 ?
C12 C11 C11 111.2(3) . 2_665 ?
C5 C6 C1 116.0(2) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 122.6(3) . . ?
C5 C4 C3 121.4(3) . . ?
C11 C12 C13 114.8(2) . . ?
C6 C5 C4 122.4(3) . . ?
C14 C13 C12 112.5(2) . . ?
C1 C2 C3 122.0(3) . . ?
C8 C7 C10 107.9(3) . . ?
C8 C7 C6 112.6(3) . . ?
C10 C7 C6 110.8(3) . . ?
C8 C7 C9 108.9(3) . . ?
C10 C7 C9 108.8(3) . . ?
C6 C7 C9 107.8(2) . . ?
C2 C1 C6 121.9(3) . . ?
N1 C14 C13 178.8(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
C3 C2 1.385(4) . ?
C3 C4 1.387(4) . ?
C3 C11 1.516(4) . ?
C11 C12 1.523(4) . ?
C11 C11 1.546(5) 2_665 ?
C6 C5 1.383(4) . ?
C6 C1 1.384(4) . ?
C6 C7 1.529(4) . ?
N1 C14 1.155(4) . ?
C4 C5 1.385(4) . ?
C12 C13 1.535(4) . ?
C13 C14 1.425(4) . ?
C2 C1 1.382(4) . ?
C7 C8 1.512(4) . ?
C7 C10 1.520(5) . ?
C7 C9 1.536(5) . ?
