#------------------------------------------------------------------------------
#$Date: 2016-03-23 00:32:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179115 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/77/4307733.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_4307733
loop_
_publ_author_name
'Guillermo A. Santillan'
'Carl J. Carrano'
_publ_section_title
;
Synthesis and Characterization of Copper(II) Complexes of Nonfacially
Coordinating Heteroscorpionate Ligands
(4-Carboxyphenyl)bis(3,5-dimethylpyrazolyl)methane and
(3-Carboxyphenyl)bis(3,5-dimethylpyrazolyl)methane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1751
_journal_page_last               1759
_journal_paper_doi               10.1021/ic062226u
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C23 H28 Cu N4 O8'
_chemical_formula_weight         552.03
_chemical_name_systematic
; 
 ? 
;
_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'
_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                 103.899(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.4844(7)
_cell_length_b                   10.9463(3)
_cell_length_c                   19.7862(5)
_cell_measurement_reflns_used    9012
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     5147.7(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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            51007
_diffrn_reflns_theta_full        26.67
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  0.8403
_exptl_absorpt_correction_T_min  0.6138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS: Area-Detector Absorption Correction'
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blue
_exptl_crystal_F_000             2296
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0548
_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)+(0.1062P)²+11.4222P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1824
_reflns_number_gt                4096
_reflns_number_total             5419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic062226usi20061229_035956.cif
_cod_data_source_block           justin112a
_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.

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' 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_database_code               4307733
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_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
Cu1 Cu 0.336931(17) 0.90663(4) 0.85006(2) 0.04545(18) Uani 1 1 d . . .
N1 N 0.38877(11) 1.0492(3) 0.84088(14) 0.0441(7) Uani 1 1 d . . .
N2 N 0.39946(11) 1.1359(3) 0.89200(15) 0.0416(6) Uani 1 1 d . . .
N3 N 0.37799(12) 0.8955(2) 0.95084(15) 0.0412(6) Uani 1 1 d . . .
N4 N 0.39833(11) 1.0007(2) 0.98434(14) 0.0380(6) Uani 1 1 d . . .
O1 O 0.10845(12) 1.1504(3) 0.93323(17) 0.0710(9) Uani 1 1 d . . .
O2 O 0.10909(12) 1.1857(4) 0.82415(16) 0.0820(11) Uani 1 1 d . . .
O3 O 0.38710(15) 0.7606(3) 0.80998(16) 0.0665(8) Uani 1 1 d . . .
H3A H 0.3785 0.7606 0.7673 0.100 Uiso 1 1 calc R . .
H3C H 0.415(3) 0.732(6) 0.823(3) 0.084(19) Uiso 1 1 d . . .
O4 O 0.29126(12) 0.9472(3) 0.76010(14) 0.0595(7) Uani 1 1 d . . .
O5 O 0.27915(12) 0.8088(3) 0.87304(15) 0.0646(8) Uani 1 1 d . . .
C1 C 0.4389(2) 1.3456(4) 0.9200(3) 0.0684(12) Uani 1 1 d . . .
H1A H 0.4280 1.3306 0.9627 0.103 Uiso 1 1 calc R . .
H1B H 0.4193 1.4159 0.8973 0.103 Uiso 1 1 calc R . .
H1C H 0.4787 1.3600 0.9299 0.103 Uiso 1 1 calc R . .
C2 C 0.42457(14) 1.2362(4) 0.8731(2) 0.0497(9) Uani 1 1 d . . .
C3 C 0.43145(16) 1.2109(4) 0.8083(2) 0.0587(10) Uani 1 1 d . . .
H3B H 0.4480 1.2620 0.7813 0.070 Uiso 1 1 calc R . .
C4 C 0.40957(16) 1.0960(4) 0.7897(2) 0.0541(10) Uani 1 1 d . . .
C5 C 0.4080(2) 1.0254(5) 0.7250(2) 0.0731(13) Uani 1 1 d . . .
H5A H 0.3907 0.9473 0.7278 0.110 Uiso 1 1 calc R . .
H5B H 0.4456 1.0136 0.7198 0.110 Uiso 1 1 calc R . .
H5C H 0.3865 1.0696 0.6856 0.110 Uiso 1 1 calc R . .
C6 C 0.46726(16) 1.0764(4) 1.0899(2) 0.0515(9) Uani 1 1 d . . .
H6A H 0.4553 1.1544 1.0696 0.077 Uiso 1 1 calc R . .
H6B H 0.5068 1.0664 1.0935 0.077 Uiso 1 1 calc R . .
H6C H 0.4601 1.0718 1.1355 0.077 Uiso 1 1 calc R . .
C7 C 0.43568(12) 0.9780(3) 1.04540(16) 0.0388(7) Uani 1 1 d . . .
C8 C 0.43772(15) 0.8539(3) 1.05204(17) 0.0446(8) Uani 1 1 d . . .
H8A H 0.4590 0.8101 1.0895 0.054 Uiso 1 1 calc R . .
C9 C 0.40209(14) 0.8048(3) 0.99258(17) 0.0434(7) Uani 1 1 d . . .
C10 C 0.3896(2) 0.6746(4) 0.9739(2) 0.0599(10) Uani 1 1 d . . .
H10A H 0.3631 0.6699 0.9295 0.090 Uiso 1 1 calc R . .
H10B H 0.3740 0.6364 1.0087 0.090 Uiso 1 1 calc R . .
H10C H 0.4237 0.6335 0.9715 0.090 Uiso 1 1 calc R . .
C11 C 0.37725(13) 1.1171(3) 0.95333(17) 0.0378(7) Uani 1 1 d . . .
H11A H 0.3920 1.1819 0.9869 0.045 Uiso 1 1 calc R . .
C12 C 0.31318(13) 1.1251(3) 0.93478(17) 0.0365(7) Uani 1 1 d . . .
C13 C 0.28307(15) 1.0840(3) 0.98130(18) 0.0458(8) Uani 1 1 d . . .
H13A H 0.3017 1.0475 1.0229 0.055 Uiso 1 1 calc R . .
C14 C 0.22507(15) 1.0974(3) 0.96575(19) 0.0461(8) Uani 1 1 d . . .
H14A H 0.2051 1.0704 0.9974 0.055 Uiso 1 1 calc R . .
C15 C 0.19653(13) 1.1503(3) 0.90388(17) 0.0396(7) Uani 1 1 d . . .
C16 C 0.22705(14) 1.1907(3) 0.85819(18) 0.0469(8) Uani 1 1 d . . .
H16A H 0.2085 1.2259 0.8162 0.056 Uiso 1 1 calc R . .
C17 C 0.28498(14) 1.1796(3) 0.87398(18) 0.0439(8) Uani 1 1 d . . .
H17A H 0.3050 1.2094 0.8431 0.053 Uiso 1 1 calc R . .
C18 C 0.13287(15) 1.1630(4) 0.8856(2) 0.0483(8) Uani 1 1 d . . .
C19 C 0.1880(3) 0.7599(8) 0.8817(4) 0.113(2) Uani 1 1 d . . .
H19A H 0.2100 0.7213 0.9229 0.169 Uiso 1 1 calc R . .
H19B H 0.1660 0.6995 0.8521 0.169 Uiso 1 1 calc R . .
H19C H 0.1635 0.8195 0.8945 0.169 Uiso 1 1 calc R . .
C20 C 0.22645(18) 0.8216(4) 0.8438(3) 0.0677(12) Uani 1 1 d . . .
C21 C 0.20518(19) 0.8836(5) 0.7822(3) 0.0724(13) Uani 1 1 d . . .
H21A H 0.1663 0.8871 0.7657 0.087 Uiso 1 1 calc R . .
C22 C 0.23740(19) 0.9400(4) 0.7439(2) 0.0645(12) Uani 1 1 d . . .
C23 C 0.2093(3) 1.0003(5) 0.6758(3) 0.102(2) Uani 1 1 d . . .
H23A H 0.2374 1.0365 0.6555 0.153 Uiso 1 1 calc R . .
H23B H 0.1840 1.0626 0.6840 0.153 Uiso 1 1 calc R . .
H23C H 0.1885 0.9403 0.6445 0.153 Uiso 1 1 calc R . .
O7 O -0.0061(2) 1.1176(5) 0.8774(4) 0.139(2) Uani 1 1 d . . .
O6 O -0.0011(7) 1.2594(15) 0.7634(16) 0.546(17) Uani 1 1 d . . .
O8 O 0.0447(4) 0.9605(10) 0.7807(10) 0.418(12) 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'
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'
Cu Cu 0.3201 1.2651 '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
O4 Cu1 O5 92.91(13) . . ?
O4 Cu1 N3 168.11(12) . . ?
O5 Cu1 N3 87.28(12) . . ?
O4 Cu1 N1 88.66(12) . . ?
O5 Cu1 N1 163.13(13) . . ?
N3 Cu1 N1 87.78(11) . . ?
O4 Cu1 O3 94.75(12) . . ?
O5 Cu1 O3 100.48(14) . . ?
N3 Cu1 O3 96.90(12) . . ?
N1 Cu1 O3 96.13(12) . . ?
C4 N1 N2 104.7(3) . . ?
C4 N1 Cu1 135.6(3) . . ?
N2 N1 Cu1 118.5(2) . . ?
C2 N2 N1 112.2(3) . . ?
C2 N2 C11 128.9(3) . . ?
N1 N2 C11 118.4(3) . . ?
C9 N3 N4 105.8(3) . . ?
C9 N3 Cu1 134.5(2) . . ?
N4 N3 Cu1 118.0(2) . . ?
C7 N4 N3 111.7(3) . . ?
C7 N4 C11 129.3(3) . . ?
N3 N4 C11 119.0(2) . . ?
C22 O4 Cu1 123.7(3) . . ?
C20 O5 Cu1 123.4(3) . . ?
N2 C2 C3 105.2(4) . . ?
N2 C2 C1 122.0(3) . . ?
C3 C2 C1 132.8(4) . . ?
C2 C3 C4 107.9(3) . . ?
N1 C4 C3 109.9(4) . . ?
N1 C4 C5 121.0(4) . . ?
C3 C4 C5 129.1(4) . . ?
N4 C7 C8 105.7(3) . . ?
N4 C7 C6 122.8(3) . . ?
C8 C7 C6 131.5(3) . . ?
C7 C8 C9 107.6(3) . . ?
N3 C9 C8 109.2(3) . . ?
N3 C9 C10 121.7(3) . . ?
C8 C9 C10 129.1(3) . . ?
N4 C11 N2 108.0(3) . . ?
N4 C11 C12 113.1(3) . . ?
N2 C11 C12 111.1(3) . . ?
C17 C12 C13 119.2(3) . . ?
C17 C12 C11 120.5(3) . . ?
C13 C12 C11 120.2(3) . . ?
C12 C13 C14 119.9(3) . . ?
C15 C14 C13 120.9(3) . . ?
C16 C15 C14 118.5(3) . . ?
C16 C15 C18 120.1(3) . . ?
C14 C15 C18 121.4(3) . . ?
C15 C16 C17 120.8(3) . . ?
C12 C17 C16 120.6(3) . . ?
O1 C18 O2 124.7(3) . . ?
O1 C18 C15 117.6(3) . . ?
O2 C18 C15 117.7(3) . . ?
O5 C20 C21 125.0(4) . . ?
O5 C20 C19 114.0(5) . . ?
C21 C20 C19 120.9(5) . . ?
C22 C21 C20 124.4(4) . . ?
O4 C22 C21 125.8(4) . . ?
O4 C22 C23 114.7(5) . . ?
C21 C22 C23 119.5(5) . . ?
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
Cu1 O4 1.913(3) . ?
Cu1 O5 1.914(3) . ?
Cu1 N3 2.010(3) . ?
Cu1 N1 2.047(3) . ?
Cu1 O3 2.272(3) . ?
N1 C4 1.340(5) . ?
N1 N2 1.365(4) . ?
N2 C2 1.354(5) . ?
N2 C11 1.459(4) . ?
N3 C9 1.335(4) . ?
N3 N4 1.362(4) . ?
N4 C7 1.352(4) . ?
N4 C11 1.455(4) . ?
O1 C18 1.239(5) . ?
O2 C18 1.240(5) . ?
O4 C22 1.282(5) . ?
O5 C20 1.289(5) . ?
C1 C2 1.503(6) . ?
C2 C3 1.362(6) . ?
C3 C4 1.382(6) . ?
C4 C5 1.489(6) . ?
C6 C7 1.485(5) . ?
C7 C8 1.364(5) . ?
C8 C9 1.393(5) . ?
C9 C10 1.485(5) . ?
C11 C12 1.525(4) . ?
C12 C17 1.372(5) . ?
C12 C13 1.385(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.383(5) . ?
C15 C16 1.377(5) . ?
C15 C18 1.519(5) . ?
C16 C17 1.383(5) . ?
C19 C20 1.498(7) . ?
C20 C21 1.383(7) . ?
C21 C22 1.366(7) . ?
C22 C23 1.510(7) . ?
O6 O6 0.55(7) 2_556 ?
