#------------------------------------------------------------------------------
#$Date: 2016-03-23 22:30:31 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179483 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/80/4338096.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_4338096
loop_
_publ_author_name
'Liu, Min-Min'
'Hou, Juan-Juan'
'Qi, Zhi-Kai'
'Duan, Li Na'
'Ji, Wen-Juan'
'Han, Cai-Yun'
'Zhang, Xian-Ming'
_publ_section_title
;
 Tuning of valence States, bonding types, hierarchical structures, and
 physical properties in copper/halide/isonicotinate system.
;
_journal_issue                   8
_journal_name_full               'Inorganic chemistry'
_journal_page_first              4130
_journal_page_last               4143
_journal_paper_doi               10.1021/ic5001232
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C14 H13 Cl Cu2 N2 O8'
_chemical_formula_sum            'C14 H13 Cl Cu2 N2 O8'
_chemical_formula_weight         499.79
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-01-12
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.6352(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3747(4)
_cell_length_b                   12.1459(4)
_cell_length_c                   12.6348(5)
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.390
_cell_measurement_theta_min      2.327
_cell_volume                     1743.73(11)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6149
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.61
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.588233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
R(int) was 0.0489 before and 0.0162 after correction.
The Ratio of minimum to maximum transmission is 0.5882.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0263
_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)+(0.0490P)²+0.3758P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                2668
_reflns_number_total             2933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic5001232_si_002.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 4338090--4338098.cif.'
_cod_database_code               4338096
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, 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
Cu2 Cu -0.01427(3) 0.89476(2) 0.40088(2) 0.02329(12) Uani 1 1 d .
Cu1 Cu 0.11391(3) 0.37740(2) 0.88819(2) 0.02422(12) Uani 1 1 d .
Cl1 Cl 0.15339(6) 0.95742(5) 0.48411(5) 0.03050(17) Uani 1 1 d .
O1 O 0.10151(18) 0.48674(15) 0.77534(15) 0.0357(5) Uani 1 1 d .
N1 N -0.01295(19) 0.76525(17) 0.50068(16) 0.0266(5) Uani 1 1 d .
O6 O 0.08520(16) 0.25995(15) 0.78027(14) 0.0293(4) Uani 1 1 d .
O5W O 0.14722(18) 0.49229(15) 0.99400(14) 0.0332(4) Uani 1 1 d .
H5WA H 0.1135 0.5520 0.9739 0.050 Uiso 1 1 d R
H5WB H 0.2214 0.5028 1.0007 0.050 Uiso 1 1 d R
O8 O -0.16593(16) 0.84282(14) 0.34243(13) 0.0288(4) Uani 1 1 d .
O4 O 0.11252(17) 0.27051(15) 1.00483(14) 0.0343(5) Uani 1 1 d .
N2 N -0.00390(19) 0.00430(17) 1.28219(16) 0.0245(5) Uani 1 1 d .
C3 C 0.0024(3) 0.5313(2) 0.7548(2) 0.0282(6) Uani 1 1 d .
O7 O 0.29894(16) 0.32596(14) 0.85896(14) 0.0286(4) Uani 1 1 d D
H7 H 0.322(3) 0.2942(18) 0.9141(11) 0.043 Uiso 1 1 d D
O2 O -0.08773(19) 0.51750(18) 0.80510(15) 0.0432(5) Uani 1 1 d .
C14 C 0.1081(3) 0.10697(19) 1.1605(2) 0.0272(6) Uani 1 1 d .
H14 H 0.1807 0.1223 1.1328 0.033 Uiso 1 1 calc R
C10 C 0.0072(2) 0.1605(2) 1.12191(19) 0.0242(5) Uani 1 1 d .
C9 C 0.0128(3) 0.2484(2) 1.03805(18) 0.0267(6) Uani 1 1 d .
C4 C -0.0041(2) 0.60961(19) 0.6620(2) 0.0246(6) Uani 1 1 d .
C13 C 0.0990(2) 0.0312(2) 1.2401(2) 0.0266(6) Uani 1 1 d .
H13 H 0.1673 -0.0034 1.2663 0.032 Uiso 1 1 calc R
C2 C 0.1719(2) 0.22233(19) 0.73562(18) 0.0234(5) Uani 1 1 d .
C8 C -0.0983(3) 0.6807(2) 0.6483(2) 0.0317(6) Uani 1 1 d .
H8 H -0.1606 0.6770 0.6933 0.038 Uiso 1 1 calc R
C7 C -0.0994(2) 0.7570(2) 0.5679(2) 0.0318(6) Uani 1 1 d .
H7A H -0.1631 0.8048 0.5600 0.038 Uiso 1 1 calc R
C5 C 0.0833(3) 0.6146(2) 0.5895(2) 0.0359(7) Uani 1 1 d .
H5 H 0.1462 0.5658 0.5940 0.043 Uiso 1 1 calc R
C12 C -0.1018(2) 0.0536(2) 1.2427(2) 0.0308(6) Uani 1 1 d .
H12 H -0.1738 0.0346 1.2696 0.037 Uiso 1 1 calc R
C11 C -0.0994(3) 0.1319(2) 1.1631(2) 0.0319(6) Uani 1 1 d .
H11 H -0.1688 0.1651 1.1375 0.038 Uiso 1 1 calc R
O3 O -0.08103(18) 0.29403(15) 1.00782(15) 0.0363(5) Uani 1 1 d .
C1 C 0.2951(2) 0.2536(2) 0.7718(2) 0.0346(7) Uani 1 1 d D
H1A H 0.3387 0.1874 0.7909 0.041 Uiso 1 1 calc R
H1B H 0.3335 0.2882 0.7135 0.041 Uiso 1 1 calc R
C6 C 0.0758(3) 0.6930(2) 0.5105(2) 0.0375(7) Uani 1 1 d .
H6 H 0.1348 0.6957 0.4620 0.045 Uiso 1 1 calc R
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
N1 Cu2 Cl1 89.42(7) . .
O8 Cu2 Cl1 174.38(6) . .
O8 Cu2 N1 88.02(8) . .
O8 Cu2 N2 90.73(8) . 1_564
N2 Cu2 Cl1 92.69(6) 1_564 .
N2 Cu2 N1 169.48(9) 1_564 .
O1 Cu1 O6 89.03(8) . .
O1 Cu1 O5W 91.10(8) . .
O1 Cu1 O4 175.08(8) . .
O1 Cu1 O7 96.10(8) . .
O6 Cu1 O7 79.23(7) . .
O5W Cu1 O6 178.29(8) . .
O5W Cu1 O4 88.10(8) . .
O5W Cu1 O7 99.06(7) . .
O4 Cu1 O6 91.92(8) . .
O4 Cu1 O7 88.82(7) . .
C3 O1 Cu1 118.36(17) . .
C7 N1 Cu2 118.20(17) . .
C7 N1 C6 117.9(2) . .
C6 N1 Cu2 123.59(17) . .
C2 O6 Cu1 117.72(16) . .
C2 O8 Cu2 120.86(17) 3_566 .
C9 O4 Cu1 115.49(16) . .
C13 N2 Cu2 122.41(17) . 1_546
C12 N2 Cu2 119.79(17) . 1_546
C12 N2 C13 117.8(2) . .
O1 C3 C4 116.1(2) . .
O2 C3 O1 125.8(2) . .
O2 C3 C4 118.1(2) . .
C1 O7 Cu1 107.89(15) . .
C13 C14 C10 118.9(3) . .
C14 C10 C9 121.1(2) . .
C11 C10 C14 118.4(2) . .
C11 C10 C9 120.5(2) . .
O4 C9 C10 117.0(2) . .
O3 C9 O4 125.2(2) . .
O3 C9 C10 117.8(2) . .
C8 C4 C3 120.0(2) . .
C8 C4 C5 117.8(2) . .
C5 C4 C3 122.1(2) . .
N2 C13 C14 123.2(2) . .
O6 C2 O8 124.6(2) . 3_566
O6 C2 C1 121.1(2) . .
O8 C2 C1 114.3(2) 3_566 .
C7 C8 C4 119.6(2) . .
N1 C7 C8 122.6(2) . .
C6 C5 C4 119.2(3) . .
N2 C12 C11 122.2(3) . .
C10 C11 C12 119.4(3) . .
O7 C1 C2 113.0(2) . .
N1 C6 C5 122.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu2 Cl1 2.2667(7) .
Cu2 N1 2.0156(19) .
Cu2 O8 1.9499(18) .
Cu2 N2 2.0122(19) 1_564
Cu1 O1 1.9489(17) .
Cu1 O6 1.9900(18) .
Cu1 O5W 1.9574(18) .
Cu1 O4 1.9646(17) .
Cu1 O7 2.2422(19) .
O1 C3 1.267(3) .
N1 C7 1.332(3) .
N1 C6 1.339(3) .
O6 C2 1.245(3) .
O8 C2 1.264(3) 3_566
O4 C9 1.256(3) .
N2 Cu2 2.0122(19) 1_546
N2 C13 1.349(3) .
N2 C12 1.341(3) .
C3 O2 1.242(3) .
C3 C4 1.509(3) .
O7 C1 1.408(3) .
C14 C10 1.388(4) .
C14 C13 1.370(4) .
C10 C9 1.508(3) .
C10 C11 1.385(4) .
C9 O3 1.247(3) .
C4 C8 1.381(4) .
C4 C5 1.383(4) .
C2 O8 1.264(3) 3_566
C2 C1 1.503(4) .
C8 C7 1.376(4) .
C5 C6 1.379(4) .
C12 C11 1.386(4) .
