#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/95/2019579.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019579
loop_
_publ_author_name
'Zabierowski, Piotr'
'Szklarzewicz, Janusz'
'Nitek, Wojciech'
_publ_section_title
;
 Disentangling steric and electronic factors in monomeric
 bis(2-bromo-4-chloro-6-{[(2-hydroxyethyl)imino]methyl}phenolato-κ²N,O)copper(II)
;
_journal_coeditor_code           FM3019
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              659
_journal_page_last               661
_journal_paper_doi               10.1107/S2053229614012273
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Cu (C9 H8 Br1 Cl1 N1 O2)2]'
_chemical_formula_moiety         'C18 H16 Br2 Cl2 Cu N2 O4'
_chemical_formula_sum            'C18 H16 Br2 Cl2 Cu N2 O4'
_chemical_formula_weight         618.59
_chemical_name_systematic
Bis(2-bromo-4-chloro-6-{[(2-hydroxyethyl)imino]methyl}phenolato-κ²N,O)copper(II)
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.977(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1298(6)
_cell_length_b                   4.65020(10)
_cell_length_c                   16.957(2)
_cell_measurement_reflns_used    6191
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.677
_cell_measurement_theta_min      4.211
_cell_volume                     1035.18(13)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2010)
;
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Agilent SuperNova (Dual, Cu at zero, Atlas)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12608
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         71.101
_diffrn_reflns_theta_min         4.224
_exptl_absorpt_coefficient_mu    8.644
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.26583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.985
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.585
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0412P)²+0.3308P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                1774
_reflns_number_total             1998
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fm3019sup1.cf
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 2019579.cif.'
_cod_original_cell_volume        1035.20(13)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2019579
_cod_database_fobs_code          2019579
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cu Cu1 0 0.5 0.5 0.03380(14) Uani d 1
Cl Cl1 0.51349(5) 0.0906(2) 0.38758(5) 0.0743(3) Uani d 1
Br Br1 0.11786(2) -0.17824(8) 0.30816(2) 0.05847(13) Uani d 1
N N1 0.12873(15) 0.6497(4) 0.55269(11) 0.0358(4) Uani d 1
C C2 0.21922(18) 0.5765(6) 0.53272(14) 0.0390(5) Uani d 1
H H2 0.2725 0.6697 0.559 0.047 Uiso calc 1
C C3 0.24752(18) 0.3676(6) 0.47457(14) 0.0394(5) Uani d 1
C C4 0.17325(18) 0.2105(5) 0.43017(13) 0.0367(5) Uani d 1
C C5 0.21223(19) 0.0212(5) 0.37315(14) 0.0393(5) Uani d 1
C C6 0.3142(2) -0.0192(6) 0.36112(15) 0.0451(6) Uani d 1
H H6 0.3363 -0.1492 0.3234 0.054 Uiso calc 1
C C7 0.38386(19) 0.1368(7) 0.40601(16) 0.0477(6) Uani d 1
C C8 0.35205(19) 0.3276(6) 0.46146(15) 0.0461(6) Uani d 1
H H8 0.3998 0.4319 0.4908 0.055 Uiso calc 1
O O9 0.07575(13) 0.2348(4) 0.44007(10) 0.0437(4) Uani d 1
C C10 0.12363(19) 0.8628(5) 0.61661(14) 0.0391(5) Uani d 1
H H10A 0.0652 0.9871 0.6077 0.047 Uiso calc 1
H H10B 0.1844 0.9813 0.6164 0.047 Uiso calc 1
C C11 0.1148(2) 0.7177(6) 0.69618(15) 0.0446(6) Uani d 1
H H11A 0.0952 0.8595 0.7351 0.053 Uiso calc 1
H H11B 0.0615 0.5733 0.6932 0.053 Uiso calc 1
O O12 0.20696(17) 0.5858(5) 0.72096(13) 0.0584(5) Uani d 1
H H12 0.247(3) 0.715(7) 0.733(2) 0.072(12) Uiso d 1
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'
O O 0.0492 0.0322 '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'
Cu Cu -1.9646 0.5888 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O9 Cu1 O9 . 3_566 180 ?
O9 Cu1 N1 . 3_566 88.93(8) ?
O9 Cu1 N1 3_566 3_566 91.07(8) ?
O9 Cu1 N1 . . 91.07(8) y
O9 Cu1 N1 3_566 . 88.93(8) y
N1 Cu1 N1 3_566 . 180 y
C2 N1 C10 . . 115.2(2) ?
C2 N1 Cu1 . . 124.15(17) ?
C10 N1 Cu1 . . 120.62(15) ?
N1 C2 C3 . . 127.6(2) ?
N1 C2 H2 . . 116.2 ?
C3 C2 H2 . . 116.2 ?
C8 C3 C4 . . 120.7(2) ?
C8 C3 C2 . . 117.5(2) ?
C4 C3 C2 . . 121.8(2) ?
O9 C4 C5 . . 120.9(2) ?
O9 C4 C3 . . 123.7(2) ?
C5 C4 C3 . . 115.4(2) ?
C6 C5 C4 . . 123.7(2) ?
C6 C5 Br1 . . 118.62(19) ?
C4 C5 Br1 . . 117.70(18) ?
C5 C6 C7 . . 118.9(2) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C8 C7 C6 . . 120.9(2) ?
C8 C7 Cl1 . . 120.9(2) ?
C6 C7 Cl1 . . 118.2(2) ?
C7 C8 C3 . . 120.4(2) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
C4 O9 Cu1 . . 130.89(17) ?
N1 C10 C11 . . 111.2(2) ?
N1 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
N1 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108 ?
O12 C11 C10 . . 112.3(2) ?
O12 C11 H11A . . 109.1 ?
C10 C11 H11A . . 109.1 ?
O12 C11 H11B . . 109.1 ?
C10 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.9 ?
C11 O12 H12 . . 107(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 . 2.0219(19) y
Cu1 O9 . 1.8913(18) y
Cu1 O9 3_566 1.8913(18) ?
Cu1 N1 3_566 2.0219(19) ?
Cl1 C7 . 1.749(3) ?
Br1 C5 . 1.888(2) ?
N1 C2 . 1.287(3) y
N1 C10 . 1.471(3) ?
C2 C3 . 1.438(4) ?
C2 H2 . 0.93 ?
C3 C8 . 1.406(4) ?
C3 C4 . 1.423(3) ?
C4 O9 . 1.299(3) y
C4 C5 . 1.410(3) ?
C5 C6 . 1.371(4) ?
C6 C7 . 1.385(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.363(4) ?
C8 H8 . 0.93 ?
C10 C11 . 1.515(3) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 O12 . 1.414(3) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
O12 H12 . 0.821(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O12 H12 O12 2_556 0.821(19) 1.98(2) 2.760(2) 158(4)
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_site_symmetry_1
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C2 C3 . 177.7(2) ?
Cu1 N1 C2 C3 . -4.2(4) ?
N1 C2 C3 C8 . 178.7(2) ?
N1 C2 C3 C4 . 0.1(4) ?
C8 C3 C4 O9 . 179.1(2) ?
C2 C3 C4 O9 . -2.4(4) ?
C8 C3 C4 C5 . -0.8(3) ?
C2 C3 C4 C5 . 177.6(2) ?
O9 C4 C5 C6 . -178.4(2) ?
C3 C4 C5 C6 . 1.5(4) ?
O9 C4 C5 Br1 . 3.5(3) ?
C3 C4 C5 Br1 . -176.59(17) ?
C4 C5 C6 C7 . -1.2(4) ?
Br1 C5 C6 C7 . 176.9(2) ?
C5 C6 C7 C8 . 0.1(4) ?
C5 C6 C7 Cl1 . -178.0(2) ?
C6 C7 C8 C3 . 0.6(4) ?
Cl1 C7 C8 C3 . 178.6(2) ?
C4 C3 C8 C7 . -0.2(4) ?
C2 C3 C8 C7 . -178.7(2) ?
C5 C4 O9 Cu1 . -170.48(17) ?
C3 C4 O9 Cu1 . 9.6(4) y
N1 Cu1 O9 C4 3_566 169.6(2) ?
N1 Cu1 O9 C4 . -10.4(2) ?
C2 N1 C10 C11 . -93.3(3) ?
Cu1 N1 C10 C11 . 88.6(2) ?
N1 C10 C11 O12 . 72.5(3) ?
