#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:47:12 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179733 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/29/7002939.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_7002939
loop_
_publ_author_name
'Tremelling, Grant W.'
'Foxman, Bruce M.'
'Landee, Christopher P.'
'Turnbull, Mark M.'
'Willett, Roger D.'
_publ_section_title
;
 Transition metal complexes of 2-amino-3,5-dihalopyridines: Syntheses,
 structures and magnetic properties of (3,5-diCAPH)2CuX4 and
 (3,5-diBAPH)2CuX4
;
_journal_issue                   47
_journal_name_full               'Dalton Transactions'
_journal_page_first              10518
_journal_page_last               10526
_journal_paper_doi               10.1039/b914392k
_journal_year                    2009
_chemical_formula_sum            'C10 H10 Br4 Cl4 Cu N4'
_chemical_formula_weight         711.20
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 94.001(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.3124(10)
_cell_length_b                   7.9776(5)
_cell_length_c                   14.6739(9)
_cell_measurement_reflns_used    9502
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.50
_cell_volume                     1904.9(2)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45303
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.25
_exptl_absorpt_coefficient_mu    10.098
_exptl_absorpt_correction_T_max  0.2499
_exptl_absorpt_correction_T_min  0.0778
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       square
_exptl_crystal_F_000             1340
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.759
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0208
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0104P)²+2.7715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0398
_refine_ls_wR_factor_ref         0.0431
_reflns_number_gt                4929
_reflns_number_total             5541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b914392k.txt
_cod_data_source_block           mmt133
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7002939
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.797061(15) 0.06040(3) 0.821861(16) 0.01381(5) Uani 1 1 d . . .
Cl1 Cl 0.67112(3) -0.04443(7) 0.83734(3) 0.01773(10) Uani 1 1 d . . .
Cl2 Cl 0.82338(3) 0.13500(7) 0.96954(3) 0.02007(10) Uani 1 1 d . . .
Cl3 Cl 0.76938(3) 0.19847(7) 0.68701(3) 0.01783(10) Uani 1 1 d . . .
Cl4 Cl 0.92521(3) -0.01415(7) 0.79920(3) 0.01837(10) Uani 1 1 d . . .
N11 N 0.58559(11) 0.1392(2) 0.62681(12) 0.0155(3) Uani 1 1 d . . .
H11 H 0.6316(16) 0.135(3) 0.6482(17) 0.019 Uiso 1 1 d . . .
C12 C 0.57288(12) 0.2237(3) 0.54694(14) 0.0148(4) Uani 1 1 d . . .
N12 N 0.63630(12) 0.2892(3) 0.50831(14) 0.0200(4) Uani 1 1 d . . .
H12A H 0.6834(18) 0.283(3) 0.5324(18) 0.024 Uiso 1 1 d . . .
H12B H 0.6306(17) 0.343(3) 0.4602(19) 0.024 Uiso 1 1 d . . .
C13 C 0.49003(12) 0.2334(3) 0.51036(13) 0.0137(4) Uani 1 1 d . . .
Br13 Br 0.467257(13) 0.34927(3) 0.400023(14) 0.01725(5) Uani 1 1 d . . .
C14 C 0.42786(12) 0.1631(3) 0.55463(13) 0.0142(4) Uani 1 1 d . . .
H14 H 0.3726 0.1729 0.5301 0.017 Uiso 1 1 calc R . .
C15 C 0.44596(12) 0.0757(3) 0.63708(13) 0.0145(4) Uani 1 1 d . . .
Br15 Br 0.361747(13) -0.02875(3) 0.697942(14) 0.01821(5) Uani 1 1 d . . .
C16 C 0.52510(13) 0.0660(3) 0.67195(14) 0.0154(4) Uani 1 1 d . . .
H16 H 0.5381 0.0082 0.7277 0.018 Uiso 1 1 calc R . .
N21 N 0.98450(11) -0.2368(2) 1.02642(12) 0.0157(3) Uani 1 1 d . . .
H21 H 1.0309(16) -0.197(3) 1.0434(17) 0.019 Uiso 1 1 d . . .
C22 C 0.97731(12) -0.3222(3) 0.94628(13) 0.0142(4) Uani 1 1 d . . .
N22 N 1.04298(11) -0.3434(2) 0.89893(13) 0.0175(4) Uani 1 1 d . . .
H22A H 1.0889(17) -0.303(3) 0.9177(18) 0.021 Uiso 1 1 d . . .
H22B H 1.0401(16) -0.395(3) 0.8480(18) 0.021 Uiso 1 1 d . . .
C23 C 0.89874(13) -0.3881(3) 0.92045(13) 0.0153(4) Uani 1 1 d . . .
Br23 Br 0.883636(13) -0.51396(3) 0.812799(14) 0.01825(5) Uani 1 1 d . . .
C24 C 0.83445(13) -0.3649(3) 0.97376(14) 0.0168(4) Uani 1 1 d . . .
H24 H 0.7819 -0.4100 0.9557 0.020 Uiso 1 1 calc R . .
C25 C 0.84634(13) -0.2739(3) 1.05547(14) 0.0169(4) Uani 1 1 d . . .
Br25 Br 0.757349(13) -0.23573(3) 1.127546(15) 0.02366(5) Uani 1 1 d . . .
C26 C 0.92164(13) -0.2116(3) 1.08124(14) 0.0175(4) Uani 1 1 d . . .
H26 H 0.9305 -0.1512 1.1368 0.021 Uiso 1 1 calc R . .
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'
Cl Cl 0.1484 0.1585 '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
Cl4 Cu Cl1 142.50(2) . . ?
Cl4 Cu Cl2 95.53(2) . . ?
Cl1 Cu Cl2 96.61(2) . . ?
Cl4 Cu Cl3 97.51(2) . . ?
Cl1 Cu Cl3 98.08(2) . . ?
Cl2 Cu Cl3 135.84(2) . . ?
C12 N11 C16 124.27(18) . . ?
N12 C12 N11 119.37(19) . . ?
N12 C12 C13 124.7(2) . . ?
N11 C12 C13 115.96(18) . . ?
C14 C13 C12 121.15(18) . . ?
C14 C13 Br13 120.29(15) . . ?
C12 C13 Br13 118.55(15) . . ?
C13 C14 C15 119.64(19) . . ?
C16 C15 C14 119.25(18) . . ?
C16 C15 Br15 120.11(15) . . ?
C14 C15 Br15 120.64(15) . . ?
C15 C16 N11 119.72(19) . . ?
C22 N21 C26 124.26(19) . . ?
N22 C22 N21 119.57(19) . . ?
N22 C22 C23 124.2(2) . . ?
N21 C22 C23 116.19(18) . . ?
C24 C23 C22 121.00(19) . . ?
C24 C23 Br23 119.69(16) . . ?
C22 C23 Br23 119.30(15) . . ?
C23 C24 C25 119.6(2) . . ?
C26 C25 C24 119.79(19) . . ?
C26 C25 Br25 120.30(16) . . ?
C24 C25 Br25 119.90(15) . . ?
C25 C26 N21 119.1(2) . . ?
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
Cu Cl4 2.2206(6) . ?
Cu Cl1 2.2443(6) . ?
Cu Cl2 2.2594(6) . ?
Cu Cl3 2.2821(5) . ?
N11 C12 1.355(3) . ?
N11 C16 1.358(3) . ?
C12 N12 1.321(3) . ?
C12 C13 1.421(3) . ?
C13 C14 1.363(3) . ?
C13 Br13 1.879(2) . ?
C14 C15 1.410(3) . ?
C15 C16 1.357(3) . ?
C15 Br15 1.884(2) . ?
N21 C22 1.357(3) . ?
N21 C26 1.362(3) . ?
C22 N22 1.328(3) . ?
C22 C23 1.412(3) . ?
C23 C24 1.364(3) . ?
C23 Br23 1.873(2) . ?
C24 C25 1.403(3) . ?
C25 C26 1.354(3) . ?
C25 Br25 1.880(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 Cl3 0.79(3) 2.33(3) 3.1020(19) 163(3) .
N12 H12A Cl2 0.82(3) 2.61(3) 3.201(2) 130(2) 4_565
N12 H12A Cl3 0.82(3) 2.67(3) 3.364(2) 143(2) .
N12 H12B Cl1 0.83(3) 2.54(3) 3.311(2) 157(2) 4_565
N21 H21 Cl2 0.84(3) 2.45(3) 3.2340(19) 156(2) 3_757
N21 H21 Cl4 0.84(3) 2.91(3) 3.4928(19) 128(2) 3_757
N22 H22A Cl2 0.85(3) 2.50(3) 3.264(2) 151(2) 3_757
N22 H22A Cl3 0.85(3) 2.86(3) 3.4073(19) 124(2) 2_746
N22 H22B Cl4 0.85(3) 2.46(3) 3.284(2) 163(2) 2_746
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 N11 C12 N12 -179.5(2) . . . . ?
C16 N11 C12 C13 0.0(3) . . . . ?
N12 C12 C13 C14 -179.7(2) . . . . ?
N11 C12 C13 C14 0.8(3) . . . . ?
N12 C12 C13 Br13 -0.8(3) . . . . ?
N11 C12 C13 Br13 179.74(14) . . . . ?
C12 C13 C14 C15 -1.5(3) . . . . ?
Br13 C13 C14 C15 179.63(15) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C13 C14 C15 Br15 -178.04(15) . . . . ?
C14 C15 C16 N11 -0.4(3) . . . . ?
Br15 C15 C16 N11 178.87(15) . . . . ?
C12 N11 C16 C15 -0.2(3) . . . . ?
C26 N21 C22 N22 -178.3(2) . . . . ?
C26 N21 C22 C23 -0.3(3) . . . . ?
N22 C22 C23 C24 178.3(2) . . . . ?
N21 C22 C23 C24 0.4(3) . . . . ?
N22 C22 C23 Br23 -0.1(3) . . . . ?
N21 C22 C23 Br23 -178.00(15) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
Br23 C23 C24 C25 178.50(16) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C23 C24 C25 Br25 178.15(16) . . . . ?
C24 C25 C26 N21 0.8(3) . . . . ?
Br25 C25 C26 N21 -178.05(16) . . . . ?
C22 N21 C26 C25 -0.3(3) . . . . ?
