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#$Date: 2019-11-22 21:45:04 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516550.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_4516550
loop_
_publ_author_name
'Carlotto, Silvia'
'Casarin, Maurizio'
'Lanza, Arianna'
'Nestola, Fabrizio'
'Pandolfo, Luciano'
'Pettinari, Claudio'
'Scatena, Rebecca'
_publ_section_title
;
 Reaction of Copper(II) Chloroacetate with Pyrazole. Synthesis of a
 One-Dimensional Coordination Polymer and Unexpected Dehydrochlorination
 Reaction
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5910
_journal_paper_doi               10.1021/acs.cgd.5b01365
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C22 H30 Cl2 Cu4 N8 O12'
_chemical_formula_sum            'C22 H30 Cl2 Cu4 N8 O12'
_chemical_formula_weight         923.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                90
_cell_angle_beta                 109.0254(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.49653(9)
_cell_length_b                   16.08972(15)
_cell_length_c                   12.88024(14)
_cell_measurement_reflns_used    21259
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      30.7680
_cell_measurement_theta_min      2.0850
_cell_volume                     1664.63(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      297(2)
_diffrn_detector_type            'Pilatus 200/300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset, Pilatus 200/300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36780
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.043
_diffrn_reflns_theta_min         2.097
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.751
_exptl_absorpt_correction_T_max  0.758
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.4632
_exptl_crystal_size_mid          0.1539
_exptl_crystal_size_min          0.1243
_refine_diff_density_max         1.167
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         5161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0506P)²+1.1106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4599
_reflns_number_total             5161
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b01365_si_003.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4516550
_shelx_shelxl_version_number     2014/7
_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   0.362
_shelx_estimated_absorpt_t_max   0.726
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu2 Cu 0.78582(3) -0.14021(2) 0.95547(2) 0.03286(7) Uani 1 1 d . .
Cu1 Cu 0.92652(3) 0.03347(2) 0.87110(2) 0.03078(7) Uani 1 1 d . .
Cl1 Cl 1.18813(12) 0.08497(6) 0.60571(6) 0.0763(2) Uani 1 1 d . .
O3 O 0.7204(2) 0.18459(10) 1.02921(15) 0.0468(4) Uani 1 1 d . .
O4 O 1.0508(2) 0.08840(11) 0.78572(13) 0.0438(3) Uani 1 1 d . .
O1 O 0.81260(18) -0.01904(8) 0.96138(12) 0.0349(3) Uani 1 1 d . .
O5 O 1.2777(2) 0.14118(10) 0.90960(13) 0.0452(4) Uani 1 1 d . .
O2 O 0.86898(19) 0.13585(8) 0.92905(13) 0.0375(3) Uani 1 1 d . .
O6 O 0.5075(2) -0.15275(14) 0.86799(15) 0.0557(5) Uani 1 1 d D .
N2 N 0.9210(2) -0.07002(11) 0.79385(14) 0.0348(3) Uani 1 1 d . .
N1 N 0.8530(2) -0.13896(10) 0.82335(14) 0.0354(3) Uani 1 1 d . .
N4 N 0.9787(3) -0.29658(12) 0.9966(2) 0.0516(5) Uani 1 1 d . .
H4N H 1.0700 -0.2687 1.0147 0.062 Uiso 1 1 calc R U
N3 N 0.8274(2) -0.26290(11) 0.97256(16) 0.0400(4) Uani 1 1 d . .
C8 C 0.7688(2) 0.12637(12) 0.98505(17) 0.0334(4) Uani 1 1 d . .
C7 C 0.7112(2) 0.03812(12) 0.99393(18) 0.0354(4) Uani 1 1 d . .
H7A H 0.7171 0.0269 1.0691 0.042 Uiso 1 1 calc R U
H7B H 0.5963 0.0318 0.9474 0.042 Uiso 1 1 calc R U
C10 C 1.2689(4) 0.14326(19) 0.7275(2) 0.0579(7) Uani 1 1 d . .
H10A H 1.3880 0.1339 0.7574 0.069 Uiso 1 1 calc R U
H10B H 1.2514 0.2019 0.7099 0.069 Uiso 1 1 calc R U
C3 C 0.9604(3) -0.08858(15) 0.70361(17) 0.0437(5) Uani 1 1 d . .
H3 H 1.0092 -0.0521 0.6671 0.052 Uiso 1 1 calc R U
C4 C 0.7220(3) -0.32575(16) 0.9495(3) 0.0587(7) Uani 1 1 d . .
H4 H 0.6070 -0.3208 0.9302 0.070 Uiso 1 1 calc R U
C9 C 1.1900(3) 0.12161(13) 0.81494(17) 0.0377(4) Uani 1 1 d . .
C2 C 0.9176(3) -0.16996(16) 0.67317(19) 0.0499(5) Uani 1 1 d . .
H2 H 0.9304 -0.1986 0.6137 0.060 Uiso 1 1 calc R U
C1 C 0.8512(3) -0.19927(14) 0.75109(19) 0.0448(5) Uani 1 1 d . .
H1 H 0.8112 -0.2529 0.7530 0.054 Uiso 1 1 calc R U
C11 C 0.4262(4) -0.1304(3) 0.7591(3) 0.0856(12) Uani 1 1 d . .
H11A H 0.3092 -0.1414 0.7408 0.128 Uiso 1 1 calc R U
H11B H 0.4429 -0.0722 0.7497 0.128 Uiso 1 1 calc R U
H11C H 0.4703 -0.1621 0.7118 0.128 Uiso 1 1 calc R U
C5 C 0.8079(4) -0.40058(17) 0.9581(3) 0.0676(8) Uani 1 1 d . .
H5 H 0.7631 -0.4538 0.9454 0.081 Uiso 1 1 calc R U
C6 C 0.9691(4) -0.37925(17) 0.9887(3) 0.0644(8) Uani 1 1 d . .
H6 H 1.0585 -0.4157 1.0020 0.077 Uiso 1 1 calc R U
H6M H 0.445(4) -0.161(2) 0.912(2) 0.061(9) Uiso 1 1 d 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'
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'
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
O1 Cu2 N1 87.74(6) . .
O1 Cu2 O5 92.01(6) . 3_757
N1 Cu2 O5 178.97(7) . 3_757
O1 Cu2 N3 163.82(7) . .
N1 Cu2 N3 90.84(8) . .
O5 Cu2 N3 89.12(7) 3_757 .
O1 Cu2 O6 101.32(7) . .
N1 Cu2 O6 96.94(7) . .
O5 Cu2 O6 84.09(7) 3_757 .
N3 Cu2 O6 94.85(8) . .
N2 Cu1 O1 90.02(6) . .
N2 Cu1 O2 164.79(7) . .
O1 Cu1 O2 84.32(6) . .
N2 Cu1 O4 91.52(7) . .
O1 Cu1 O4 177.27(7) . .
O2 Cu1 O4 94.72(7) . .
N2 Cu1 O1 103.04(6) . 3_757
O1 Cu1 O1 85.34(6) . 3_757
O2 Cu1 O1 90.60(6) . 3_757
O4 Cu1 O1 92.12(6) . 3_757
C9 O4 Cu1 131.12(14) . .
C7 O1 Cu1 111.55(11) . .
C7 O1 Cu2 125.71(11) . .
Cu1 O1 Cu2 119.05(7) . .
C9 O5 Cu2 127.57(15) . 3_757
C8 O2 Cu1 114.21(12) . .
C11 O6 Cu2 124.79(19) . .
C11 O6 H6M 118(2) . .
Cu2 O6 H6M 116(2) . .
C3 N2 N1 107.97(17) . .
C3 N2 Cu1 131.74(15) . .
N1 N2 Cu1 119.98(12) . .
C1 N1 N2 107.82(18) . .
C1 N1 Cu2 130.77(15) . .
N2 N1 Cu2 121.35(12) . .
C6 N4 N3 110.9(2) . .
C6 N4 H4N 124.6 . .
N3 N4 H4N 124.6 . .
C4 N3 N4 105.8(2) . .
C4 N3 Cu2 130.40(17) . .
N4 N3 Cu2 123.15(14) . .
O3 C8 O2 123.16(18) . .
O3 C8 C7 120.75(18) . .
O2 C8 C7 116.09(17) . .
O1 C7 C8 110.07(15) . .
O1 C7 H7A 109.6 . .
C8 C7 H7A 109.6 . .
O1 C7 H7B 109.6 . .
C8 C7 H7B 109.6 . .
H7A C7 H7B 108.2 . .
C9 C10 Cl1 113.44(18) . .
C9 C10 H10A 108.9 . .
Cl1 C10 H10A 108.9 . .
C9 C10 H10B 108.9 . .
Cl1 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
N2 C3 C2 109.8(2) . .
N2 C3 H3 125.1 . .
C2 C3 H3 125.1 . .
N3 C4 C5 110.2(2) . .
N3 C4 H4 124.9 . .
C5 C4 H4 124.9 . .
O4 C9 O5 127.91(19) . .
O4 C9 C10 118.6(2) . .
O5 C9 C10 113.4(2) . .
C3 C2 C1 104.43(19) . .
C3 C2 H2 127.8 . .
C1 C2 H2 127.8 . .
N1 C1 C2 109.9(2) . .
N1 C1 H1 125.0 . .
C2 C1 H1 125.0 . .
O6 C11 H11A 109.5 . .
O6 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O6 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C6 C5 C4 105.1(2) . .
C6 C5 H5 127.5 . .
C4 C5 H5 127.5 . .
N4 C6 C5 108.0(3) . .
N4 C6 H6 126.0 . .
C5 C6 H6 126.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu2 O1 1.9615(14) .
Cu2 N1 1.9637(18) .
Cu2 O5 1.9810(16) 3_757
Cu2 N3 2.0048(18) .
Cu2 O6 2.2725(18) .
Cu1 N2 1.9325(17) .
Cu1 O1 1.9331(13) .
Cu1 O2 1.9359(15) .
Cu1 O4 1.9655(15) .
Cu1 O1 2.5504(16) 3_757
Cl1 C10 1.764(3) .
O3 C8 1.234(3) .
O4 C9 1.239(3) .
O1 C7 1.414(2) .
O5 C9 1.245(3) .
O5 Cu2 1.9809(16) 3_757
O2 C8 1.292(2) .
O6 C11 1.394(4) .
O6 H6M 0.910(18) .
N2 C3 1.344(3) .
N2 N1 1.361(2) .
N1 C1 1.341(3) .
N4 C6 1.334(3) .
N4 N3 1.335(3) .
N4 H4N 0.8600 .
N3 C4 1.318(3) .
C8 C7 1.518(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C10 C9 1.527(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C3 C2 1.381(4) .
C3 H3 0.9300 .
C4 C5 1.393(4) .
C4 H4 0.9300 .
C2 C1 1.384(4) .
C2 H2 0.9300 .
C1 H1 0.9300 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C5 C6 1.340(4) .
C5 H5 0.9300 .
C6 H6 0.9300 .
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
N4 H4N O3 0.86 2.45 3.233(3) 152.4 3_757
N4 H4N O2 0.86 2.26 2.911(3) 132.2 3_757
C3 H3 Cl1 0.93 2.93 3.837(3) 165.4 .
C4 H4 Cl1 0.93 2.84 3.619(3) 142.6 2_646
C2 H2 O3 0.93 2.65 3.414(3) 139.8 2_646
C6 H6 Cl1 0.93 2.92 3.550(3) 126.5 2_746
O6 H6M O3 0.910(18) 1.834(19) 2.727(2) 166(3) 3_657
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
C3 N2 N1 C1 0.0(2) .
Cu1 N2 N1 C1 174.41(15) .
C3 N2 N1 Cu2 177.49(15) .
Cu1 N2 N1 Cu2 -8.1(2) .
C6 N4 N3 C4 0.1(3) .
C6 N4 N3 Cu2 -171.6(2) .
Cu1 O2 C8 O3 179.08(17) .
Cu1 O2 C8 C7 -1.2(2) .
Cu1 O1 C7 C8 -20.7(2) .
Cu2 O1 C7 C8 -178.67(12) .
O3 C8 C7 O1 -165.55(19) .
O2 C8 C7 O1 14.7(3) .
N1 N2 C3 C2 0.3(3) .
Cu1 N2 C3 C2 -173.24(17) .
N4 N3 C4 C5 -0.5(3) .
Cu2 N3 C4 C5 170.4(2) .
Cu1 O4 C9 O5 -13.2(4) .
Cu1 O4 C9 C10 167.41(18) .
Cu2 O5 C9 O4 -9.0(3) 3_757
Cu2 O5 C9 C10 170.46(17) 3_757
Cl1 C10 C9 O4 -22.1(3) .
Cl1 C10 C9 O5 158.45(19) .
N2 C3 C2 C1 -0.4(3) .
N2 N1 C1 C2 -0.3(3) .
Cu2 N1 C1 C2 -177.44(17) .
C3 C2 C1 N1 0.4(3) .
N3 C4 C5 C6 0.7(4) .
N3 N4 C6 C5 0.4(4) .
C4 C5 C6 N4 -0.6(4) .
