#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012302.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_2012302
loop_
_publ_author_name
'Liu, Xiaoming'
'Kilner, Colin A.'
'Thornton-Pett, Mark'
'Halcrow, Malcolm A.'
_publ_section_title
;
 Two complexes of CuBr₂ with 5-tert-butylpyrazole
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1253
_journal_page_last               1255
_journal_paper_doi               10.1107/S0108270101012653
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '[Cu Br2 (C7 H12 N2)4]'
_chemical_formula_moiety         'C28 H48 Br2 Cu N8'
_chemical_formula_sum            'C28 H48 Br2 Cu N8'
_chemical_formula_weight         720.10
_chemical_name_systematic
;
trans-dibromotetrakis(5-tert-butylpyrazole-N²)copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.8260(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.5985(3)
_cell_length_b                   11.9918(2)
_cell_length_c                   15.9131(2)
_cell_measurement_reflns_used    29739
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.68
_cell_volume                     3518.24(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       area-detector
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .077
_diffrn_reflns_av_sigmaI/netI    .032
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            29739
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    2.921
_exptl_absorpt_correction_T_max  .637
_exptl_absorpt_correction_T_min  .329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SORTAV; Blessing, 1995)'
_exptl_crystal_colour            'Deep blue'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular prism'
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          .49
_exptl_crystal_size_mid          .34
_exptl_crystal_size_min          .17
_refine_diff_density_max         .26
_refine_diff_density_min         -.44
_refine_ls_extinction_coef       .0027(2)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          .0300
_refine_ls_R_factor_gt           .0263
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0327P)²+2.2831P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0702
_reflns_number_gt                3655
_reflns_number_total             4019
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1461.cif
_cod_data_source_block           II
_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 

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.

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2012302
_cod_database_fobs_code          2012302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 .2500 .2500 .0000 .03027(10) Uani d S 1 . . Cu
N2 .35090(8) .31214(12) .05144(9) .0314(3) Uani d . 1 . . N
N3 .41078(8) .24737(13) .06997(10) .0303(3) Uani d . 1 . . N
H3 .4028(11) .1775(18) .0576(13) .031(5) Uiso d . 1 . . H
C4 .47233(9) .30750(15) .09398(12) .0331(4) Uani d . 1 . . C
C5 .45117(11) .41710(17) .09161(17) .0488(5) Uani d . 1 . . C
H5 .4812 .4794 .1052 .059 Uiso calc R 1 . . H
C6 .37558(11) .41606(17) .06466(15) .0457(5) Uani d . 1 . . C
H6 .3466 .4793 .0570 .055 Uiso calc R 1 . . H
C7 .54601(10) .25549(16) .11226(13) .0381(4) Uani d . 1 . . C
C8 .56461(15) .2589(3) .02676(18) .0686(8) Uani d . 1 . . C
H8A .6115 .2261 .0376 .082 Uiso calc R 1 . . H
H8B .5652 .3349 .0081 .082 Uiso calc R 1 . . H
H8C .5289 .2178 -.0192 .082 Uiso calc R 1 . . H
C9 .60229(13) .3221(2) .18558(18) .0640(7) Uani d . 1 . . C
H9A .6493 .2893 .1976 .077 Uiso calc R 1 . . H
H9B .5898 .3210 .2389 .077 Uiso calc R 1 . . H
H9C .6030 .3978 .1662 .077 Uiso calc R 1 . . H
C10 .54679(14) .1342(2) .1417(2) .0708(8) Uani d . 1 . . C
H10A .5943 .1034 .1531 .085 Uiso calc R 1 . . H
H10B .5120 .0922 .0953 .085 Uiso calc R 1 . . H
H10C .5346 .1308 .1952 .085 Uiso calc R 1 . . H
N11 .24815(8) .20208(12) .11981(9) .0303(3) Uani d . 1 . . N
N12 .20697(8) .25908(12) .15857(10) .0284(3) Uani d . 1 . . N
H12 .1929(11) .3200(18) .1395(13) .031(5) Uiso d . 1 . . H
C13 .19824(9) .20293(14) .22722(10) .0282(3) Uani d . 1 . . C
C14 .23621(11) .10438(16) .23377(12) .0370(4) Uani d . 1 . . C
H14 .2411 .0475 .2751 .044 Uiso calc R 1 . . H
C15 .26576(10) .10787(16) .16548(12) .0363(4) Uani d . 1 . . C
H15 .2940 .0517 .1536 .044 Uiso calc R 1 . . H
C16 .15555(10) .24795(15) .28280(12) .0346(4) Uani d . 1 . . C
C17 .11354(12) .35283(18) .24082(14) .0451(5) Uani d . 1 . . C
H17A .0869 .3796 .2774 .054 Uiso calc R 1 . . H
H17B .0804 .3356 .1823 .054 Uiso calc R 1 . . H
H17C .1469 .4093 .2364 .054 Uiso calc R 1 . . H
C18 .10189(17) .1578(2) .2878(2) .0751(9) Uani d . 1 . . C
H18A .0738 .1845 .3227 .090 Uiso calc R 1 . . H
H18B .1280 .0921 .3151 .090 Uiso calc R 1 . . H
H18C .0701 .1402 .2286 .090 Uiso calc R 1 . . H
C19 .20784(15) .2747(2) .37618(14) .0625(7) Uani d . 1 . . C
H19A .1812 .3036 .4120 .075 Uiso calc R 1 . . H
H19B .2424 .3293 .3721 .075 Uiso calc R 1 . . H
H19C .2329 .2080 .4032 .075 Uiso calc R 1 . . H
Br20 .181354(10) .468494(13) .023977(11) .03249(8) Uani d . 1 . . Br
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu .3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 '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
N2 Cu1 N11 . . 92.96(6) yes
N2 Cu1 Br20 . . 92.62(4) yes
N11 Cu1 Br20 . . 88.63(4) yes
N2 Cu1 N11 . 7 87.04(6) ?
N11 Cu1 Br20 7 . 91.37(4) ?
N2 Cu1 Br20 7 . 87.38(4) ?
N2 Cu1 N2 7 . 180 ?
N11 Cu1 N11 7 . 180 ?
Br20 Cu1 Br20 7 . 180 ?
C6 N2 N3 . . 105.17(14) ?
C6 N2 Cu1 . . 131.92(13) ?
N3 N2 Cu1 . . 122.46(11) ?
C4 N3 N2 . . 112.47(15) ?
C4 N3 H3 . . 131.5(13) ?
N2 N3 H3 . . 115.5(13) ?
N3 C4 C5 . . 105.76(16) ?
N3 C4 C7 . . 122.76(16) ?
C5 C4 C7 . . 131.36(18) ?
C4 C5 C6 . . 106.18(18) ?
C4 C5 H5 . . 126.9 ?
C6 C5 H5 . . 126.9 ?
N2 C6 C5 . . 110.42(17) ?
N2 C6 H6 . . 124.8 ?
C5 C6 H6 . . 124.8 ?
C4 C7 C8 . . 108.67(16) ?
C4 C7 C10 . . 111.25(17) ?
C8 C7 C10 . . 108.6(2) ?
C4 C7 C9 . . 109.05(17) ?
C8 C7 C9 . . 109.7(2) ?
C10 C7 C9 . . 109.5(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C15 N11 N12 . . 105.36(14) ?
C15 N11 Cu1 . . 132.97(12) ?
N12 N11 Cu1 . . 119.62(11) ?
C13 N12 N11 . . 112.17(14) ?
C13 N12 H12 . . 129.9(15) ?
N11 N12 H12 . . 117.9(15) ?
N12 C13 C14 . . 106.03(15) ?
N12 C13 C16 . . 123.14(15) ?
C14 C13 C16 . . 130.82(16) ?
C13 C14 C15 . . 105.72(15) ?
C13 C14 H14 . . 127.1 ?
C15 C14 H14 . . 127.1 ?
N11 C15 C14 . . 110.70(16) ?
N11 C15 H15 . . 124.6 ?
C14 C15 H15 . . 124.6 ?
C13 C16 C19 . . 108.86(16) ?
C13 C16 C17 . . 111.23(15) ?
C19 C16 C17 . . 109.71(17) ?
C13 C16 C18 . . 107.78(16) ?
C19 C16 C18 . . 110.2(2) ?
C17 C16 C18 . . 109.06(19) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
H3 Br20 H12 7 . 76.1(6) ?
H3 Br20 Cu1 7 . 64.1(5) ?
H12 Br20 Cu1 . . 63.0(5) ?
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 N2 . 2.0094(14) yes
Cu1 N11 . 2.0032(14) yes
Cu1 Br20 . 3.02801(16) yes
N2 C6 . 1.328(3) ?
N2 N3 . 1.354(2) ?
N3 C4 . 1.345(2) ?
N3 H3 . .86(2) ?
C4 C5 . 1.375(3) ?
C4 C7 . 1.508(2) ?
C5 C6 . 1.396(3) ?
C5 H5 . .9300 ?
C6 H6 . .9300 ?
C7 C8 . 1.524(3) ?
C7 C10 . 1.526(3) ?
C7 C9 . 1.531(3) ?
C8 H8A . .9600 ?
C8 H8B . .9600 ?
C8 H8C . .9600 ?
C9 H9A . .9600 ?
C9 H9B . .9600 ?
C9 H9C . .9600 ?
C10 H10A . .9600 ?
C10 H10B . .9600 ?
C10 H10C . .9600 ?
N11 C15 . 1.324(2) ?
N11 N12 . 1.355(2) ?
N12 C13 . 1.343(2) ?
N12 H12 . .80(2) ?
C13 C14 . 1.382(3) ?
C13 C16 . 1.509(2) ?
C14 C15 . 1.395(3) ?
C14 H14 . .9300 ?
C15 H15 . .9300 ?
C16 C19 . 1.526(3) ?
C16 C17 . 1.527(3) ?
C16 C18 . 1.528(3) ?
C17 H17A . .9600 ?
C17 H17B . .9600 ?
C17 H17C . .9600 ?
C18 H18A . .9600 ?
C18 H18B . .9600 ?
C18 H18C . .9600 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .9600 ?
Br20 H3 7 2.45(2) ?
Br20 H12 . 2.51(2) ?
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
N3 H3 Br20 7 .86(2) 2.45(2) 3.2195(15) 148(2)
N12 H12 Br20 . .80(2) 2.51(2) 3.2275(15) 149(2)
