#------------------------------------------------------------------------------
#$Date: 2017-07-14 04:08:15 +0300 (Fri, 14 Jul 2017) $
#$Revision: 198702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/04/7120444.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_7120444
loop_
_publ_author_name
'Rovira, Mireia'
'Jašíková, Lucie'
'Andris, Erik'
'Acuña-Pares, Ferran'
'Soler, Marta'
'Güell, Imma'
'Wang, Ming-Zheng'
'Gomez, Laura'
'Luis, Josep M.'
'Roithova, Jana'
'Ribas, Xavi'
_publ_section_title
;
 CuI/CuIII prototypical organometallic mechanism for the deactivation of
 an active pincer-like CuI catalyst in Ullmann-type couplings
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04491G
_journal_year                    2017
_chemical_formula_moiety         'C9 H15 Br Cu N3, 0.33(O H2)'
_chemical_formula_sum            'C9 H15.66 Br Cu N3 O0.33'
_chemical_formula_weight         314.68
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 113.710(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.533(12)
_cell_length_b                   15.50(2)
_cell_length_c                   8.885(11)
_cell_measurement_reflns_used    5681
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      2.33
_cell_volume                     1202(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13398
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    5.113
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.645998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             627
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.606
_refine_diff_density_rms
'0.109 &#x00EF;&#x00BB;&#x00BF;#######################################################################'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+1.8506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2437
_reflns_number_total             2909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc04491g2.cif
_cod_data_source_block           mingbr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7120444
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.73842(5) 0.10265(3) 0.74896(5) 0.04558(16) Uani 1 1 d .
Cu1 Cu 0.56026(6) 0.16284(4) 0.47502(7) 0.04337(18) Uani 1 1 d .
N1 N 0.4288(4) 0.2779(2) 0.4935(4) 0.0337(7) Uani 1 1 d .
C1 C 0.2780(4) 0.2667(3) 0.3981(5) 0.0363(8) Uani 1 1 d .
N2 N 0.3378(4) 0.1101(2) 0.4091(5) 0.0406(8) Uani 1 1 d .
H2 H 0.320(6) 0.064(4) 0.345(7) 0.055(15) Uiso 1 1 d .
C2 C 0.1711(5) 0.3330(3) 0.3710(5) 0.0426(10) Uani 1 1 d .
H2A H 0.0659 0.3229 0.3044 0.051 Uiso 1 1 calc R
N3 N 0.6818(4) 0.3138(2) 0.8319(4) 0.0361(7) Uani 1 1 d .
H3 H 0.663(6) 0.257(4) 0.805(7) 0.054(15) Uiso 1 1 d .
C3 C 0.2187(6) 0.4136(3) 0.4414(6) 0.0458(10) Uani 1 1 d .
H3A H 0.1479 0.4596 0.4227 0.055 Uiso 1 1 calc R
C4 C 0.3743(6) 0.4248(3) 0.5405(5) 0.0434(10) Uani 1 1 d .
H4A H 0.4110 0.4791 0.5901 0.052 Uiso 1 1 calc R
C5 C 0.4751(5) 0.3560(3) 0.5662(5) 0.0377(8) Uani 1 1 d .
C6 C 0.2323(5) 0.1792(3) 0.3159(6) 0.0440(10) Uani 1 1 d .
H6A H 0.1274 0.1651 0.3051 0.053 Uiso 1 1 calc R
H6B H 0.2308 0.1822 0.2040 0.053 Uiso 1 1 calc R
C8 C 0.6437(5) 0.3642(3) 0.6782(5) 0.0415(9) Uani 1 1 d .
H8A H 0.7063 0.3431 0.6198 0.050 Uiso 1 1 calc R
H8B H 0.6691 0.4257 0.7059 0.050 Uiso 1 1 calc R
C7 C 0.3087(7) 0.0822(4) 0.5538(7) 0.0576(13) Uani 1 1 d .
H7A H 0.2012 0.0649 0.5179 0.086 Uiso 1 1 calc R
H7B H 0.3304 0.1301 0.6319 0.086 Uiso 1 1 calc R
H7C H 0.3752 0.0333 0.6070 0.086 Uiso 1 1 calc R
C9 C 0.8515(5) 0.3179(4) 0.9320(7) 0.0571(13) Uani 1 1 d .
H9A H 0.8784 0.2804 1.0284 0.086 Uiso 1 1 calc R
H9B H 0.8812 0.3774 0.9681 0.086 Uiso 1 1 calc R
H9C H 0.9058 0.2985 0.8650 0.086 Uiso 1 1 calc R
O1W O 0.9345(12) 0.1619(9) 1.0265(16) 0.070(3) Uani 0.33 1 d P
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'
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'
O O 0.0106 0.0060 '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
N3 Cu1 N2 129.94(15) 4_565 .
N3 Cu1 N1 112.15(15) 4_565 .
N2 Cu1 N1 78.40(15) . .
N3 Cu1 Br1 109.39(14) 4_565 .
N2 Cu1 Br1 109.53(12) . .
N1 Cu1 Br1 113.98(10) . .
C1 N1 C5 118.1(3) . .
C1 N1 Cu1 109.8(3) . .
C5 N1 Cu1 131.6(3) . .
N1 C1 C2 122.0(4) . .
N1 C1 C6 116.3(4) . .
C2 C1 C6 121.7(4) . .
C6 N2 C7 112.0(4) . .
C6 N2 Cu1 104.8(3) . .
C7 N2 Cu1 112.8(3) . .
C6 N2 H2 109(4) . .
C7 N2 H2 105(4) . .
Cu1 N2 H2 114(3) . .
C3 C2 C1 120.0(4) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C8 N3 C9 109.3(4) . .
C8 N3 Cu1 118.9(3) . 4_566
C9 N3 Cu1 111.4(3) . 4_566
C8 N3 H3 108(3) . .
C9 N3 H3 104(3) . .
Cu1 N3 H3 104(3) 4_566 .
C2 C3 C4 117.8(4) . .
C2 C3 H3A 121.1 . .
C4 C3 H3A 121.1 . .
C5 C4 C3 119.8(4) . .
C5 C4 H4A 120.1 . .
C3 C4 H4A 120.1 . .
N1 C5 C4 122.2(4) . .
N1 C5 C8 116.2(4) . .
C4 C5 C8 121.6(4) . .
N2 C6 C1 112.3(3) . .
N2 C6 H6A 109.1 . .
C1 C6 H6A 109.1 . .
N2 C6 H6B 109.1 . .
C1 C6 H6B 109.1 . .
H6A C6 H6B 107.9 . .
N3 C8 C5 111.2(3) . .
N3 C8 H8A 109.4 . .
C5 C8 H8A 109.4 . .
N3 C8 H8B 109.4 . .
C5 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
N2 C7 H7A 109.5 . .
N2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
N2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N3 C9 H9A 109.5 . .
N3 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N3 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
Br1 Cu1 2.521(2) .
Cu1 N3 2.068(4) 4_565
Cu1 N2 2.124(4) .
Cu1 N1 2.223(4) .
N1 C1 1.355(5) .
N1 C5 1.360(5) .
C1 C2 1.398(6) .
C1 C6 1.518(6) .
N2 C6 1.475(6) .
N2 C7 1.484(6) .
N2 H2 0.89(6) .
C2 C3 1.389(7) .
C2 H2A 0.9500 .
N3 C8 1.485(6) .
N3 C9 1.502(6) .
N3 Cu1 2.068(4) 4_566
N3 H3 0.91(6) .
C3 C4 1.398(7) .
C3 H3A 0.9500 .
C4 C5 1.391(6) .
C4 H4A 0.9500 .
C5 C8 1.518(6) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
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
N3 Cu1 N1 C1 105.0(3) 4_565
N2 Cu1 N1 C1 -23.6(3) .
Br1 Cu1 N1 C1 -130.0(2) .
N3 Cu1 N1 C5 -67.1(4) 4_565
N2 Cu1 N1 C5 164.3(4) .
Br1 Cu1 N1 C5 57.9(3) .
C5 N1 C1 C2 1.1(5) .
Cu1 N1 C1 C2 -172.2(3) .
C5 N1 C1 C6 178.4(3) .
Cu1 N1 C1 C6 5.1(4) .
N3 Cu1 N2 C6 -73.4(3) 4_565
N1 Cu1 N2 C6 35.9(3) .
Br1 Cu1 N2 C6 147.4(2) .
N3 Cu1 N2 C7 164.5(3) 4_565
N1 Cu1 N2 C7 -86.2(3) .
Br1 Cu1 N2 C7 25.4(3) .
N1 C1 C2 C3 0.7(6) .
C6 C1 C2 C3 -176.5(4) .
C1 C2 C3 C4 -1.0(6) .
C2 C3 C4 C5 -0.3(6) .
C1 N1 C5 C4 -2.5(5) .
Cu1 N1 C5 C4 169.1(3) .
C1 N1 C5 C8 177.2(3) .
Cu1 N1 C5 C8 -11.2(5) .
C3 C4 C5 N1 2.2(6) .
C3 C4 C5 C8 -177.6(4) .
C7 N2 C6 C1 77.8(5) .
Cu1 N2 C6 C1 -44.8(4) .
N1 C1 C6 N2 27.1(5) .
C2 C1 C6 N2 -155.6(4) .
C9 N3 C8 C5 175.4(4) .
Cu1 N3 C8 C5 -55.3(4) 4_566
N1 C5 C8 N3 -70.6(4) .
C4 C5 C8 N3 109.2(4) .
