#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:52:01 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179132 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/94/4309441.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_4309441
loop_
_publ_author_name
'Chang-Chuan Chou'
'Chan-Cheng Su'
'Andrew Yeh'
_publ_section_title
;
Mononuclear and Dinuclear Copper(I) Complexes of
Bis(3,5-dimethylpyrazol-1-yl)methane: Synthesis, Structure, and Reactivity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6122
_journal_page_last               6128
_journal_paper_doi               10.1021/ic050568e
_journal_volume                  44
_journal_year                    2005
_chemical_formula_moiety         'C16 H22 Cl1 Cu1 N4 O5'
_chemical_formula_sum            'C12 H16 Cl Cu N4 O5'
_chemical_formula_weight         395.28
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.1980(10)
_cell_angle_beta                 97.5550(10)
_cell_angle_gamma                103.242(2)
_cell_formula_units_Z            2
_cell_length_a                   7.7670(3)
_cell_length_b                   9.7260(4)
_cell_length_c                   12.1940(5)
_cell_measurement_reflns_used    16038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     805.55(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 19'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0705
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9001
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    1.551
_exptl_absorpt_correction_T_max  0.8599
_exptl_absorpt_correction_T_min  0.7478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.885
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0449
_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)+(0.0711P)²+1.4206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                2404
_reflns_number_total             2797
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050568esi20050412_085511_2.cif
_cod_data_source_block           3229
_cod_database_code               4309441
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3834(6) 0.0757(6) 0.2447(4) 0.0291(10) Uani 1 1 d . . .
H1A H 0.4398 0.0456 0.3032 0.044 Uiso 1 1 calc R . .
H1B H 0.2904 -0.0133 0.1822 0.044 Uiso 1 1 calc R . .
H1C H 0.3298 0.1549 0.2848 0.044 Uiso 1 1 calc R . .
C2 C 0.5239(6) 0.1380(5) 0.1884(4) 0.0214(9) Uani 1 1 d . . .
C3 C 0.4995(6) 0.1948(5) 0.0988(4) 0.0224(9) Uani 1 1 d . . .
H3 H 0.3959 0.2045 0.0533 0.027 Uiso 1 1 d R . .
C4 C 0.6702(6) 0.2428(5) 0.0800(4) 0.0216(9) Uani 1 1 d . . .
C5 C 0.7305(6) 0.3178(5) -0.0017(4) 0.0261(10) Uani 1 1 d . . .
H5A H 0.6272 0.3278 -0.0473 0.031 Uiso 1 1 d R . .
H5B H 0.7874 0.2541 -0.0571 0.031 Uiso 1 1 d R . .
H5C H 0.8163 0.4191 0.0471 0.031 Uiso 1 1 d R . .
C6 C 0.9778(6) 0.2253(5) 0.1627(4) 0.0215(9) Uani 1 1 d . . .
H6A H 0.9936 0.1257 0.1498 0.026 Uiso 1 1 d R . .
H6B H 1.0164 0.2551 0.1011 0.026 Uiso 1 1 d R . .
C7 C 1.2881(6) 0.5274(5) 0.2192(4) 0.0246(10) Uani 1 1 d . . .
H7A H 1.2088 0.4595 0.1401 0.037 Uiso 1 1 d R . .
H7B H 1.4113 0.5276 0.2171 0.037 Uiso 1 1 d R . .
H7C H 1.2806 0.6312 0.2412 0.037 Uiso 1 1 d R . .
C8 C 1.2328(6) 0.4691(5) 0.3109(4) 0.0215(9) Uani 1 1 d . . .
C9 C 1.3039(6) 0.5264(5) 0.4348(4) 0.0208(9) Uani 1 1 d . . .
H9 H 1.4026 0.6156 0.4915 0.025 Uiso 1 1 d R . .
C10 C 1.1996(6) 0.4270(5) 0.4758(4) 0.0199(9) Uani 1 1 d . . .
C11 C 1.2176(6) 0.4345(5) 0.6017(4) 0.0246(10) Uani 1 1 d . . .
H11A H 1.3174 0.5237 0.6571 0.030 Uiso 1 1 d R . .
H11B H 1.2399 0.3415 0.6021 0.030 Uiso 1 1 d R . .
H11C H 1.1069 0.4432 0.6265 0.030 Uiso 1 1 d R . .
C12 C 0.7614(6) 0.1109(6) 0.4898(4) 0.0300(11) Uani 1 1 d . . .
Cl1 Cl 0.87274(13) -0.19456(12) 0.19218(9) 0.0210(3) Uani 1 1 d . . .
Cu1 Cu 0.84702(7) 0.14969(6) 0.37032(4) 0.0204(2) Uani 1 1 d . . .
N1 N 0.6979(5) 0.1475(4) 0.2218(3) 0.0196(8) Uani 1 1 d . . .
N2 N 0.7863(5) 0.2130(4) 0.1548(3) 0.0194(8) Uani 1 1 d . . .
N3 N 1.0917(5) 0.3394(4) 0.2815(3) 0.0192(8) Uani 1 1 d . . .
N4 N 1.0701(5) 0.3112(4) 0.3823(3) 0.0185(7) Uani 1 1 d . . .
O1 O 0.7005(5) 0.0871(6) 0.5619(4) 0.0552(12) Uani 1 1 d . . .
O2 O 0.9687(4) -0.0434(4) 0.2928(3) 0.0315(8) Uani 1 1 d . . .
O3 O 0.8829(5) -0.1784(5) 0.0807(3) 0.0400(9) Uani 1 1 d . . .
O4 O 0.9638(5) -0.3038(4) 0.2019(3) 0.0344(8) Uani 1 1 d . . .
O5 O 0.6874(4) -0.2413(4) 0.1982(3) 0.0384(9) Uani 1 1 d . . .
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'
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'
N N 0.0061 0.0033 '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
_geom_angle_publ_flag
N1 C2 C3 110.6(4) . . ?
N1 C2 C1 121.3(4) . . ?
C3 C2 C1 128.1(4) . . ?
C4 C3 C2 106.0(4) . . ?
N2 C4 C3 106.3(4) . . ?
N2 C4 C5 123.2(4) . . ?
C3 C4 C5 130.4(4) . . ?
N2 C6 N3 111.9(3) . . ?
N3 C8 C9 105.8(4) . . ?
N3 C8 C7 123.2(4) . . ?
C9 C8 C7 130.9(4) . . ?
C8 C9 C10 107.1(4) . . ?
N4 C10 C9 110.1(4) . . ?
N4 C10 C11 120.4(4) . . ?
C9 C10 C11 129.5(4) . . ?
O1 C12 Cu1 176.8(4) . . ?
O5 Cl1 O4 111.1(2) . . ?
O5 Cl1 O3 110.6(2) . . ?
O4 Cl1 O3 110.0(2) . . ?
O5 Cl1 O2 109.5(2) . . ?
O4 Cl1 O2 108.0(2) . . ?
O3 Cl1 O2 107.5(2) . . ?
C12 Cu1 N4 129.65(18) . . ?
C12 Cu1 N1 126.30(17) . . ?
N4 Cu1 N1 95.26(14) . . ?
C12 Cu1 O2 102.35(19) . . ?
N4 Cu1 O2 92.36(13) . . ?
N1 Cu1 O2 103.46(13) . . ?
C2 N1 N2 105.2(3) . . ?
C2 N1 Cu1 133.1(3) . . ?
N2 N1 Cu1 118.4(3) . . ?
C4 N2 N1 111.8(3) . . ?
C4 N2 C6 129.4(4) . . ?
N1 N2 C6 118.4(3) . . ?
C8 N3 N4 111.6(3) . . ?
C8 N3 C6 129.8(4) . . ?
N4 N3 C6 118.3(3) . . ?
C10 N4 N3 105.3(3) . . ?
C10 N4 Cu1 133.8(3) . . ?
N3 N4 Cu1 119.6(2) . . ?
Cl1 O2 Cu1 125.19(18) . . ?
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
C1 C2 1.496(6) . ?
C2 N1 1.331(6) . ?
C2 C3 1.409(6) . ?
C3 C4 1.380(6) . ?
C4 N2 1.354(5) . ?
C4 C5 1.503(6) . ?
C6 N2 1.452(5) . ?
C6 N3 1.454(5) . ?
C7 C8 1.501(6) . ?
C8 N3 1.357(6) . ?
C8 C9 1.379(6) . ?
C9 C10 1.398(6) . ?
C10 N4 1.338(5) . ?
C10 C11 1.496(6) . ?
C12 O1 1.124(6) . ?
C12 Cu1 1.806(5) . ?
Cl1 O5 1.427(3) . ?
Cl1 O4 1.435(3) . ?
Cl1 O3 1.436(3) . ?
Cl1 O2 1.455(3) . ?
Cu1 N4 2.001(3) . ?
Cu1 N1 2.007(3) . ?
Cu1 O2 2.240(3) . ?
N1 N2 1.374(5) . ?
N3 N4 1.379(5) . ?
