#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:58:55 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272749 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158417.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_7158417
loop_
_publ_author_name
'Camats, Marc'
'Favier, Isabelle'
'Mallet-Ladeira, Sonia'
'Pla, Daniel'
'Gómez, Montserrat'
_publ_section_title
;
 Understanding Cu(II)-based systems for C(sp³)-H bond
 functionalization: insights into the synthesis of aza-heterocycles.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              219
_journal_page_last               227
_journal_paper_doi               10.1039/d1ob02118d
_journal_volume                  20
_journal_year                    2021
_chemical_formula_moiety         'C18 H22 Br4 Cu2 F2 N4'
_chemical_formula_sum            'C18 H22 Br4 Cu2 F2 N4'
_chemical_formula_weight         779.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-12 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_cell_angle_alpha                71.537(2)
_cell_angle_beta                 79.335(2)
_cell_angle_gamma                70.634(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8883(6)
_cell_length_b                   8.1714(7)
_cell_length_c                   10.3538(8)
_cell_measurement_reflns_used    6626
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.75
_cell_volume                     594.83(8)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16362
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.269
_diffrn_source                   'Incoatec microfocus sealed tube'
_exptl_absorpt_coefficient_mu    8.534
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_description       needle
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0136P)²+0.5897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2338
_reflns_number_total             2720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02118d2.cif
_cod_data_source_block           CuA
_cod_depositor_comments
'Adding full bibliography for 7158417--7158420.cif.'
_cod_database_code               7158417
_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. 
;
_shelx_estimated_absorpt_t_min   0.224
_shelx_estimated_absorpt_t_max   0.628
loop_
_space_group_symop_operation_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
Cu1 Cu 0.46642(4) 0.78358(4) 0.58999(3) 0.02159(8) Uani 1 1 d . . . . .
Br1 Br 0.74491(3) 0.86109(4) 0.50101(3) 0.02598(7) Uani 1 1 d . . . . .
Br2 Br 0.52132(4) 0.74356(4) 0.81864(3) 0.03326(8) Uani 1 1 d . . . . .
F1 F 0.1027(2) 0.6110(2) 0.31238(17) 0.0373(4) Uani 1 1 d . . . . .
N1 N 0.4400(3) 0.7457(3) 0.4076(2) 0.0220(4) Uani 1 1 d . . . . .
N2 N 0.2497(3) 0.6851(3) 0.6468(2) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.5318(4) 0.7884(4) 0.2864(3) 0.0257(6) Uani 1 1 d . . . . .
H1 H 0.632110 0.830995 0.280336 0.031 Uiso 1 1 calc R U . . .
C2 C 0.4857(4) 0.7727(4) 0.1687(3) 0.0279(6) Uani 1 1 d . . . . .
H2 H 0.553765 0.805043 0.083883 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3421(4) 0.7104(4) 0.1748(3) 0.0286(6) Uani 1 1 d . . . . .
H3 H 0.309409 0.696635 0.095873 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2474(3) 0.6689(4) 0.3008(3) 0.0260(6) Uani 1 1 d . . . . .
C5 C 0.2962(3) 0.6864(3) 0.4156(2) 0.0212(5) Uani 1 1 d . . . . .
C6 C 0.1999(3) 0.6488(3) 0.5520(3) 0.0239(5) Uani 1 1 d . . . . .
H6 H 0.102552 0.598595 0.568943 0.029 Uiso 1 1 calc R U . . .
C7 C 0.1469(4) 0.6549(4) 0.7819(3) 0.0290(6) Uani 1 1 d . . . . .
H7A H 0.231720 0.587508 0.853390 0.035 Uiso 1 1 calc R U . . .
H7B H 0.068244 0.580742 0.785607 0.035 Uiso 1 1 calc R U . . .
C8 C 0.0323(4) 0.8315(4) 0.8104(3) 0.0337(7) Uani 1 1 d . . . . .
H8A H -0.057280 0.896454 0.742001 0.040 Uiso 1 1 calc R U . . .
H8B H 0.109715 0.908494 0.802685 0.040 Uiso 1 1 calc R U . . .
C9 C -0.0651(4) 0.7958(5) 0.9537(3) 0.0397(7) Uani 1 1 d . . . . .
H9A H -0.147182 0.725813 0.959298 0.060 Uiso 1 1 calc R U . . .
H9B H -0.134246 0.910912 0.972939 0.060 Uiso 1 1 calc R U . . .
H9C H 0.023673 0.727682 1.020878 0.060 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N2 Cu1 N1 80.11(8) . . ?
N2 Cu1 Br2 94.48(6) . . ?
N1 Cu1 Br2 165.05(6) . . ?
N2 Cu1 Br1 170.04(6) . . ?
N1 Cu1 Br1 92.33(6) . . ?
Br2 Cu1 Br1 91.240(14) . . ?
N2 Cu1 Br1 93.48(6) . 2_676 ?
N1 Cu1 Br1 88.27(6) . 2_676 ?
Br2 Cu1 Br1 106.057(15) . 2_676 ?
Br1 Cu1 Br1 92.761(13) . 2_676 ?
Cu1 Br1 Cu1 87.238(13) . 2_676 ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cu1 128.78(17) . . ?
C5 N1 Cu1 112.13(16) . . ?
C6 N2 C7 118.0(2) . . ?
C6 N2 Cu1 114.37(17) . . ?
C7 N2 Cu1 127.58(17) . . ?
N1 C1 C2 122.2(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
F1 C4 C5 118.8(2) . . ?
F1 C4 C3 119.5(2) . . ?
C5 C4 C3 121.6(2) . . ?
N1 C5 C4 120.5(2) . . ?
N1 C5 C6 114.8(2) . . ?
C4 C5 C6 124.7(2) . . ?
N2 C6 C5 118.4(2) . . ?
N2 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C8 111.4(2) . . ?
N2 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N2 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 110.0(2) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Cu1 N2 2.039(2) . ?
Cu1 N1 2.065(2) . ?
Cu1 Br2 2.3862(4) . ?
Cu1 Br1 2.4249(4) . ?
Cu1 Br1 2.7813(5) 2_676 ?
Cu1 Cu1 3.6008(7) 2_676 ?
F1 C4 1.347(3) . ?
N1 C1 1.331(3) . ?
N1 C5 1.354(3) . ?
N2 C6 1.269(3) . ?
N2 C7 1.472(3) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C5 C6 1.465(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.514(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.526(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
