#------------------------------------------------------------------------------
#$Date: 2017-03-02 08:09:48 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192767 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/53/1545382.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_1545382
loop_
_publ_author_name
'Chkirate, Karim'
'Sebbar, Nada Kheira'
'Ouzidan, Younes'
'Essassi, El Mokhtar'
'Mague, Joel T.'
_publ_section_title
;
 trans-Bis(N-{2-[2-(3-methyl-1H-pyrazol-5-yl-κN²)acetamido-κO]phenyl}benzamide)bis(perchlorato-κO)copper(II)
;
_journal_coeditor_code           ZQ4016
_journal_issue                   2
_journal_name_full               IUCrData
_journal_page_first              x170285
_journal_paper_doi               10.1107/S2414314617002851
_journal_volume                  2
_journal_year                    2017
_chemical_formula_iupac          '[Cu (C19 H18 N4 O2)2 (Cl O4)2]'
_chemical_formula_moiety         'C38 H36 Cl2 Cu N8 O12'
_chemical_formula_sum            'C38 H36 Cl2 Cu N8 O12'
_chemical_formula_weight         931.19
_chemical_name_systematic
trans-Bis(N-{2-[2-(3-methyl-1H-pyrazol-5-yl-κN²)acetamido-κO]phenyl}benzamide)bis(perchlorato-κO)copper(II)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                79.4060(10)
_cell_angle_beta                 86.2400(10)
_cell_angle_gamma                67.8950(10)
_cell_formula_units_Z            1
_cell_length_a                   8.6572(2)
_cell_length_b                   8.8108(2)
_cell_length_c                   14.2054(3)
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.9062
_cell_measurement_theta_min      5.5014
_cell_volume                     986.78(4)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT  (Bruker, 2016)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL 2014/7 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7804
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         71.939
_diffrn_reflns_theta_min         3.165
_exptl_absorpt_coefficient_mu    2.678
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            'pale green-blue'
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             479
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.512
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0604P)²+0.5402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                2999
_reflns_number_total             3702
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zq4016sup1.cif
_cod_data_source_block           I
_cod_database_code               1545382
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.566
_shelx_estimated_absorpt_t_max   0.948
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.5000 0.5000 0.0000 0.03299(17) Uani d 1
O O1 0.5561(2) 0.5620(2) 0.11555(12) 0.0359(4) Uani d 1
O O2 0.2816(3) 0.6621(3) 0.54249(14) 0.0454(5) Uani d 1
N N1 0.6439(3) 0.2722(3) 0.04252(15) 0.0348(5) Uani d 1
N N2 0.6726(3) 0.1487(3) -0.00892(16) 0.0393(5) Uani d 1
H H2 0.6280 0.1756 -0.0688 0.047 Uiso d 1
N N3 0.5944(3) 0.5296(3) 0.27323(14) 0.0312(5) Uani d 1
H H3A 0.6406 0.4602 0.3283 0.037 Uiso d 1
N N4 0.3221(3) 0.5880(3) 0.39480(15) 0.0331(5) Uani d 1
H H4A 0.3106 0.5185 0.3580 0.040 Uiso d 1
C C1 0.8316(5) -0.1514(4) -0.0073(3) 0.0580(9) Uani d 1
H H1A 0.8567 -0.1261 -0.0753 0.087 Uiso calc 1
H H1B 0.7407 -0.1934 -0.0007 0.087 Uiso calc 1
H H1C 0.9310 -0.2360 0.0259 0.087 Uiso calc 1
C C2 0.7805(4) 0.0020(3) 0.0353(2) 0.0388(6) Uani d 1
C C3 0.8220(4) 0.0325(3) 0.1198(2) 0.0386(6) Uani d 1
H H3 0.8957 -0.0464 0.1676 0.046 Uiso calc 1
C C4 0.7359(3) 0.2003(3) 0.12200(18) 0.0308(5) Uani d 1
C C5 0.7426(4) 0.2942(4) 0.1983(2) 0.0439(7) Uani d 1
H H5A 0.8567 0.2945 0.1991 0.053 Uiso calc 1
H H5B 0.7253 0.2313 0.2607 0.053 Uiso calc 1
C C6 0.6223(3) 0.4703(3) 0.19184(17) 0.0295(5) Uani d 1
C C7 0.4904(3) 0.6970(3) 0.28058(17) 0.0306(5) Uani d 1
C C8 0.5246(4) 0.8292(4) 0.2270(2) 0.0403(6) Uani d 1
H H8 0.6167 0.8088 0.1844 0.048 Uiso calc 1
C C9 0.4245(4) 0.9903(4) 0.2358(2) 0.0466(7) Uani d 1
H H9 0.4472 1.0810 0.1990 0.056 Uiso calc 1
C C10 0.2916(4) 1.0194(4) 0.2981(2) 0.0473(7) Uani d 1
H H10 0.2222 1.1304 0.3035 0.057 Uiso calc 1
C C11 0.2587(4) 0.8881(4) 0.3527(2) 0.0414(6) Uani d 1
H H11 0.1683 0.9093 0.3964 0.050 Uiso calc 1
C C12 0.3569(3) 0.7258(3) 0.34409(18) 0.0317(5) Uani d 1
C C13 0.2845(3) 0.5649(3) 0.48871(18) 0.0326(6) Uani d 1
C C14 0.2482(3) 0.4123(3) 0.52507(18) 0.0332(6) Uani d 1
C C15 0.1334(4) 0.4169(4) 0.5994(2) 0.0414(7) Uani d 1
H H15 0.0806 0.5160 0.6252 0.050 Uiso calc 1
C C16 0.0962(4) 0.2784(4) 0.6353(2) 0.0508(8) Uani d 1
H H16 0.0173 0.2825 0.6854 0.061 Uiso calc 1
C C17 0.1736(4) 0.1337(4) 0.5985(3) 0.0534(8) Uani d 1
H H17 0.1473 0.0385 0.6229 0.064 Uiso calc 1
C C18 0.2895(4) 0.1271(4) 0.5261(2) 0.0501(8) Uani d 1
H H18 0.3442 0.0266 0.5019 0.060 Uiso calc 1
C C19 0.3261(4) 0.2659(4) 0.4889(2) 0.0427(7) Uani d 1
H H19 0.4048 0.2611 0.4386 0.051 Uiso calc 1
Cl Cl1 0.18597(9) 0.49021(9) 0.17026(5) 0.04040(19) Uani d 1
O O3 0.3013(4) 0.3972(3) 0.24714(19) 0.0717(8) Uani d 1
O O4 0.2600(3) 0.4391(3) 0.08272(17) 0.0620(7) Uani d 1
O O5 0.0374(4) 0.4586(4) 0.1863(2) 0.0851(10) Uani d 1
O O6 0.1550(3) 0.6626(3) 0.16559(18) 0.0596(6) Uani 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
Cu Cu -1.9646 0.5888 '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'
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
N1 Cu1 N1 2_665 . 180.0
N1 Cu1 O1 2_665 . 89.97(8)
N1 Cu1 O1 . . 90.03(8)
N1 Cu1 O1 2_665 2_665 90.03(8)
N1 Cu1 O1 . 2_665 89.97(8)
O1 Cu1 O1 . 2_665 180.0
C6 O1 Cu1 . . 129.02(17)
C4 N1 N2 . . 105.5(2)
C4 N1 Cu1 . . 130.81(17)
N2 N1 Cu1 . . 123.71(17)
C2 N2 N1 . . 112.2(2)
C2 N2 H2 . . 128.9
N1 N2 H2 . . 118.5
C6 N3 C7 . . 123.7(2)
C6 N3 H3A . . 119.1
C7 N3 H3A . . 117.2
C13 N4 C12 . . 125.5(2)
C13 N4 H4A . . 118.6
C12 N4 H4A . . 115.3
C2 C1 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
N2 C2 C3 . . 105.6(2)
N2 C2 C1 . . 122.0(3)
C3 C2 C1 . . 132.4(3)
C2 C3 C4 . . 107.1(2)
C2 C3 H3 . . 126.4
C4 C3 H3 . . 126.4
N1 C4 C3 . . 109.6(2)
N1 C4 C5 . . 122.9(2)
C3 C4 C5 . . 127.4(2)
C4 C5 C6 . . 118.1(2)
C4 C5 H5A . . 107.8
C6 C5 H5A . . 107.8
C4 C5 H5B . . 107.8
C6 C5 H5B . . 107.8
H5A C5 H5B . . 107.1
O1 C6 N3 . . 120.3(2)
O1 C6 C5 . . 124.1(2)
N3 C6 C5 . . 115.5(2)
C8 C7 C12 . . 120.4(2)
C8 C7 N3 . . 120.4(2)
C12 C7 N3 . . 119.1(2)
C9 C8 C7 . . 119.8(3)
C9 C8 H8 . . 120.1
C7 C8 H8 . . 120.1
C10 C9 C8 . . 120.0(3)
C10 C9 H9 . . 120.0
C8 C9 H9 . . 120.0
C9 C10 C11 . . 120.4(3)
C9 C10 H10 . . 119.8
C11 C10 H10 . . 119.8
C10 C11 C12 . . 120.4(3)
C10 C11 H11 . . 119.8
C12 C11 H11 . . 119.8
C11 C12 C7 . . 119.0(3)
C11 C12 N4 . . 122.2(3)
C7 C12 N4 . . 118.8(2)
O2 C13 N4 . . 123.1(3)
O2 C13 C14 . . 121.4(2)
N4 C13 C14 . . 115.5(2)
C19 C14 C15 . . 119.2(3)
C19 C14 C13 . . 122.4(3)
C15 C14 C13 . . 118.4(3)
C16 C15 C14 . . 120.3(3)
C16 C15 H15 . . 119.8
C14 C15 H15 . . 119.8
C15 C16 C17 . . 120.0(3)
C15 C16 H16 . . 120.0
C17 C16 H16 . . 120.0
C16 C17 C18 . . 120.1(3)
C16 C17 H17 . . 120.0
C18 C17 H17 . . 120.0
C19 C18 C17 . . 120.3(3)
C19 C18 H18 . . 119.8
C17 C18 H18 . . 119.8
C18 C19 C14 . . 120.0(3)
C18 C19 H19 . . 120.0
C14 C19 H19 . . 120.0
O5 Cl1 O6 . . 111.27(18)
O5 Cl1 O4 . . 109.48(17)
O6 Cl1 O4 . . 109.57(15)
O5 Cl1 O3 . . 109.7(2)
O6 Cl1 O3 . . 108.17(15)
O4 Cl1 O3 . . 108.60(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N1 2_665 1.928(2)
Cu1 N1 . 1.928(2)
Cu1 O1 . 1.9652(17)
Cu1 O1 2_665 1.9653(17)
Cu1 O4 . 2.505(3)
O1 C6 . 1.252(3)
O2 C13 . 1.241(3)
N1 C4 . 1.336(3)
N1 N2 . 1.358(3)
N2 C2 . 1.345(4)
N2 H2 . 0.9099
N3 C6 . 1.326(3)
N3 C7 . 1.429(3)
N3 H3A . 0.9099
N4 C13 . 1.349(3)
N4 C12 . 1.418(3)
N4 H4A . 0.9099
C1 C2 . 1.486(4)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 C3 . 1.374(4)
C3 C4 . 1.389(4)
C3 H3 . 0.9500
C4 C5 . 1.495(4)
C5 C6 . 1.498(4)
C5 H5A . 0.9900
C5 H5B . 0.9900
C7 C8 . 1.388(4)
C7 C12 . 1.393(4)
C8 C9 . 1.381(4)
C8 H8 . 0.9500
C9 C10 . 1.378(5)
C9 H9 . 0.9500
C10 C11 . 1.382(4)
C10 H10 . 0.9500
C11 C12 . 1.385(4)
C11 H11 . 0.9500
C13 C14 . 1.488(4)
C14 C19 . 1.388(4)
C14 C15 . 1.397(4)
C15 C16 . 1.378(4)
C15 H15 . 0.9500
C16 C17 . 1.379(5)
C16 H16 . 0.9500
C17 C18 . 1.382(5)
C17 H17 . 0.9500
C18 C19 . 1.381(4)
C18 H18 . 0.9500
C19 H19 . 0.9500
Cl1 O5 . 1.411(3)
Cl1 O6 . 1.429(2)
Cl1 O4 . 1.430(2)
Cl1 O3 . 1.435(3)
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 H3A O2 2_666 0.91 1.97 2.870(3) 171
N4 H4A O3 . 0.91 2.08 2.971(3) 166
C5 H5A O5 1_655 0.99 2.48 3.358(4) 148
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
C4 N1 N2 C2 -0.5(3)
Cu1 N1 N2 C2 178.5(2)
N1 N2 C2 C3 0.6(3)
N1 N2 C2 C1 -179.8(3)
N2 C2 C3 C4 -0.5(3)
C1 C2 C3 C4 -180.0(3)
N2 N1 C4 C3 0.2(3)
Cu1 N1 C4 C3 -178.8(2)
N2 N1 C4 C5 179.0(3)
Cu1 N1 C4 C5 0.1(4)
C2 C3 C4 N1 0.2(3)
C2 C3 C4 C5 -178.6(3)
N1 C4 C5 C6 9.1(4)
C3 C4 C5 C6 -172.3(3)
Cu1 O1 C6 N3 -153.74(19)
Cu1 O1 C6 C5 29.7(4)
C7 N3 C6 O1 -0.1(4)
C7 N3 C6 C5 176.8(2)
C4 C5 C6 O1 -24.4(4)
C4 C5 C6 N3 158.8(3)
C6 N3 C7 C8 -58.0(3)
C6 N3 C7 C12 123.7(3)
C12 C7 C8 C9 -0.8(4)
N3 C7 C8 C9 -179.1(2)
C7 C8 C9 C10 0.4(4)
C8 C9 C10 C11 0.7(5)
C9 C10 C11 C12 -1.3(5)
C10 C11 C12 C7 0.9(4)
C10 C11 C12 N4 -176.5(3)
C8 C7 C12 C11 0.2(4)
N3 C7 C12 C11 178.5(2)
C8 C7 C12 N4 177.6(2)
N3 C7 C12 N4 -4.1(3)
C13 N4 C12 C11 -46.5(4)
C13 N4 C12 C7 136.2(3)
C12 N4 C13 O2 -2.4(4)
C12 N4 C13 C14 178.4(2)
O2 C13 C14 C19 -146.2(3)
N4 C13 C14 C19 33.1(4)
O2 C13 C14 C15 32.7(4)
N4 C13 C14 C15 -148.0(3)
C19 C14 C15 C16 -1.0(4)
C13 C14 C15 C16 -179.9(2)
C14 C15 C16 C17 0.6(4)
C15 C16 C17 C18 0.5(5)
C16 C17 C18 C19 -1.3(5)
C17 C18 C19 C14 0.9(5)
C15 C14 C19 C18 0.2(4)
C13 C14 C19 C18 179.1(3)

_cod_database_fobs_code 1545382
