#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:56:56 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506936.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_4506936
loop_
_publ_author_name
'Banerjee, Subhabrata'
'Kumar, Dhurjati Prasad'
'Bandyopadhay, Sabyasachi'
'Adarsh, N. N.'
'Dastidar, Parthasarathi'
_publ_section_title
;
 A New Series of CuIICoordination Polymers Derived from
 Bis-pyridyl-bis-urea Ligands and Various Dicarboxylates and Their Role in
 Methanolysis of Epoxide Ring-Opening Catalysis
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5546
_journal_paper_doi               10.1021/cg3011037
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C16 H20 Cu N7 O8'
_chemical_formula_weight         501.93
_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                74.927(2)
_cell_angle_beta                 76.612(2)
_cell_angle_gamma                87.388(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5396(8)
_cell_length_b                   9.7085(8)
_cell_length_c                   12.6295(12)
_cell_measurement_temperature    293(2)
_cell_volume                     1098.61(17)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury 2.3'
_computing_publication_material  Shelxl-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'Omega scan'
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_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            13046
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  0.8842
_exptl_absorpt_correction_T_min  0.7573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0333
_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)+(0.0367P)²+0.4328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                3169
_reflns_number_total             3830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3011037_si_007.cif
_cod_data_source_block           sb0769a_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4506936
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
Cu1 Cu 0.66463(3) 0.59578(3) -0.39721(3) 0.03287(11) Uani 1 1 d .
N1 N 0.7220(2) 0.5056(2) -0.25333(17) 0.0342(5) Uani 1 1 d .
C2 C 0.8058(3) 0.3916(3) -0.2439(2) 0.0453(7) Uani 1 1 d .
H2 H 0.8393 0.3545 -0.3059 0.054 Uiso 1 1 calc R
C3 C 0.8434(4) 0.3285(4) -0.1445(3) 0.0627(9) Uani 1 1 d .
H3 H 0.9002 0.2476 -0.1386 0.075 Uiso 1 1 calc R
C4 C 0.7974(4) 0.3844(3) -0.0535(3) 0.0599(9) Uani 1 1 d .
H4 H 0.8234 0.3420 0.0140 0.072 Uiso 1 1 calc R
C5 C 0.7122(3) 0.5042(3) -0.0626(2) 0.0400(6) Uani 1 1 d .
C6 C 0.6750(3) 0.5603(3) -0.1649(2) 0.0360(6) Uani 1 1 d .
H6 H 0.6152 0.6390 -0.1723 0.043 Uiso 1 1 calc R
N7 N 0.6650(3) 0.5606(2) 0.02986(18) 0.0466(6) Uani 1 1 d .
H7 H 0.6703 0.5067 0.0946 0.056 Uiso 1 1 calc R
C8 C 0.6099(3) 0.6967(3) 0.0271(2) 0.0413(6) Uani 1 1 d .
O9 O 0.5977(3) 0.7817(2) -0.05925(17) 0.0676(7) Uani 1 1 d .
N10 N 0.5721(2) 0.7230(2) 0.12939(18) 0.0423(6) Uani 1 1 d .
H10 H 0.5823 0.6566 0.1872 0.051 Uiso 1 1 calc R
C11 C 0.5151(3) 0.8583(3) 0.1460(2) 0.0417(7) Uani 1 1 d .
H11A H 0.4410 0.8410 0.2153 0.050 Uiso 1 1 calc R
H11B H 0.4702 0.9042 0.0846 0.050 Uiso 1 1 calc R
C12 C 0.6291(3) 0.9588(3) 0.1521(2) 0.0467(7) Uani 1 1 d .
H12A H 0.7002 0.9812 0.0811 0.056 Uiso 1 1 calc R
H12B H 0.5842 1.0471 0.1633 0.056 Uiso 1 1 calc R
C13 C 0.7031(3) 0.8949(3) 0.2459(3) 0.0496(7) Uani 1 1 d .
H13A H 0.6309 0.8573 0.3145 0.059 Uiso 1 1 calc R
H13B H 0.7614 0.8159 0.2280 0.059 Uiso 1 1 calc R
N14 N 0.7945(2) 0.9977(2) 0.2652(2) 0.0496(6) Uani 1 1 d .
H14 H 0.7724 1.0864 0.2495 0.060 Uiso 1 1 calc R
C15 C 0.9112(3) 0.9594(3) 0.3064(2) 0.0360(6) Uani 1 1 d .
O16 O 0.95753(19) 0.83782(19) 0.32313(17) 0.0461(5) Uani 1 1 d .
N17 N 0.9756(2) 1.0687(2) 0.3289(2) 0.0457(6) Uani 1 1 d .
H17 H 0.9309 1.1484 0.3216 0.055 Uiso 1 1 calc R
C18 C 1.1054(3) 1.0650(3) 0.3624(2) 0.0336(6) Uani 1 1 d .
C19 C 1.1891(3) 0.9461(3) 0.3880(2) 0.0443(7) Uani 1 1 d .
H19 H 1.1599 0.8569 0.3858 0.053 Uiso 1 1 calc R
C20 C 1.3173(3) 0.9634(3) 0.4170(2) 0.0452(7) Uani 1 1 d .
H20 H 1.3748 0.8848 0.4352 0.054 Uiso 1 1 calc R
C21 C 1.3600(3) 1.0941(3) 0.4191(2) 0.0398(6) Uani 1 1 d .
H21 H 1.4477 1.1036 0.4370 0.048 Uiso 1 1 calc R
N22 N 1.2790(2) 1.2098(2) 0.39612(17) 0.0334(5) Uani 1 1 d .
C23 C 1.1543(3) 1.1936(3) 0.3695(2) 0.0360(6) Uani 1 1 d .
H23 H 1.0971 1.2733 0.3548 0.043 Uiso 1 1 calc R
O24 O 0.59893(18) 0.40774(17) -0.40483(14) 0.0367(4) Uani 1 1 d .
O25 O 0.53513(19) 0.67390(17) -0.50057(15) 0.0363(4) Uani 1 1 d .
C26 C 0.4814(3) 0.5766(2) -0.5275(2) 0.0315(6) Uani 1 1 d .
O27 O 0.8582(3) 0.5808(3) -0.5275(2) 0.0536(6) Uani 1 1 d .
N28 N 0.2417(3) 0.6127(3) 0.7068(2) 0.0566(7) Uani 1 1 d .
O29 O 0.2938(3) 0.4944(3) 0.7110(2) 0.0817(8) Uani 1 1 d .
O30 O 0.2694(4) 0.6830(3) 0.7665(2) 0.1130(12) Uani 1 1 d .
O31 O 0.1619(3) 0.6583(3) 0.6412(2) 0.0763(7) Uani 1 1 d .
H27B H 0.882(4) 0.651(4) -0.571(3) 0.068(14) Uiso 1 1 d .
H27A H 0.853(4) 0.521(4) -0.553(3) 0.078(15) Uiso 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
O25 Cu1 N1 158.27(8) . .
O25 Cu1 O24 83.99(6) . .
N1 Cu1 O24 90.81(7) . .
O25 Cu1 N22 92.07(7) . 2_775
N1 Cu1 N22 92.78(8) . 2_775
O24 Cu1 N22 176.05(7) . 2_775
O25 Cu1 O27 97.02(9) . .
N1 Cu1 O27 103.96(9) . .
O24 Cu1 O27 88.69(10) . .
N22 Cu1 O27 92.05(10) 2_775 .
C2 N1 C6 119.7(2) . .
C2 N1 Cu1 121.00(17) . .
C6 N1 Cu1 119.27(17) . .
N1 C2 C3 120.9(3) . .
N1 C2 H2 119.5 . .
C3 C2 H2 119.5 . .
C2 C3 C4 120.0(3) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C3 C4 C5 119.8(3) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C5 C6 117.2(2) . .
C4 C5 N7 119.8(2) . .
C6 C5 N7 123.0(2) . .
N1 C6 C5 122.4(2) . .
N1 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
C5 N7 C8 125.9(2) . .
C5 N7 H7 117.0 . .
C8 N7 H7 117.0 . .
O9 C8 N10 124.0(3) . .
O9 C8 N7 122.8(2) . .
N10 C8 N7 113.3(2) . .
C8 N10 C11 122.6(2) . .
C8 N10 H10 118.7 . .
C11 N10 H10 118.7 . .
N10 C11 C12 113.3(2) . .
N10 C11 H11A 108.9 . .
C12 C11 H11A 108.9 . .
N10 C11 H11B 108.9 . .
C12 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
C13 C12 C11 111.9(2) . .
C13 C12 H12A 109.2 . .
C11 C12 H12A 109.2 . .
C13 C12 H12B 109.2 . .
C11 C12 H12B 109.2 . .
H12A C12 H12B 107.9 . .
N14 C13 C12 112.6(2) . .
N14 C13 H13A 109.1 . .
C12 C13 H13A 109.1 . .
N14 C13 H13B 109.1 . .
C12 C13 H13B 109.1 . .
H13A C13 H13B 107.8 . .
C15 N14 C13 122.4(2) . .
C15 N14 H14 118.8 . .
C13 N14 H14 118.8 . .
O16 C15 N14 123.6(2) . .
O16 C15 N17 122.5(2) . .
N14 C15 N17 114.0(2) . .
C15 N17 C18 127.2(2) . .
C15 N17 H17 116.4 . .
C18 N17 H17 116.4 . .
C23 C18 C19 117.7(2) . .
C23 C18 N17 116.1(2) . .
C19 C18 N17 126.2(2) . .
C20 C19 C18 118.2(2) . .
C20 C19 H19 120.9 . .
C18 C19 H19 120.9 . .
C21 C20 C19 120.7(2) . .
C21 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
N22 C21 C20 121.7(2) . .
N22 C21 H21 119.1 . .
C20 C21 H21 119.1 . .
C23 N22 C21 117.9(2) . .
C23 N22 Cu1 118.27(16) . 2_775
C21 N22 Cu1 123.78(16) . 2_775
N22 C23 C18 123.7(2) . .
N22 C23 H23 118.1 . .
C18 C23 H23 118.1 . .
C26 O24 Cu1 110.89(15) 2_664 .
C26 O25 Cu1 111.28(15) . .
O25 C26 O24 126.4(2) . 2_664
O25 C26 C26 116.6(2) . 2_664
O24 C26 C26 117.1(2) 2_664 2_664
Cu1 O27 H27B 114(3) . .
Cu1 O27 H27A 112(3) . .
H27B O27 H27A 113(4) . .
O30 N28 O29 119.6(3) . .
O30 N28 O31 121.5(3) . .
O29 N28 O31 118.9(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O25 1.9879(16) .
Cu1 N1 1.989(2) .
Cu1 O24 1.9897(16) .
Cu1 N22 1.9908(19) 2_775
Cu1 O27 2.198(2) .
N1 C2 1.331(3) .
N1 C6 1.336(3) .
C2 C3 1.368(4) .
C2 H2 0.9300 .
C3 C4 1.369(4) .
C3 H3 0.9300 .
C4 C5 1.384(4) .
C4 H4 0.9300 .
C5 C6 1.386(3) .
C5 N7 1.390(3) .
C6 H6 0.9300 .
N7 C8 1.394(3) .
N7 H7 0.8600 .
C8 O9 1.211(3) .
C8 N10 1.346(3) .
N10 C11 1.446(3) .
N10 H10 0.8600 .
C11 C12 1.521(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.500(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 N14 1.457(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
N14 C15 1.333(3) .
N14 H14 0.8600 .
C15 O16 1.224(3) .
C15 N17 1.372(3) .
N17 C18 1.395(3) .
N17 H17 0.8600 .
C18 C23 1.383(3) .
C18 C19 1.385(3) .
C19 C20 1.384(4) .
C19 H19 0.9300 .
C20 C21 1.359(4) .
C20 H20 0.9300 .
C21 N22 1.341(3) .
C21 H21 0.9300 .
N22 C23 1.335(3) .
N22 Cu1 1.9908(19) 2_775
C23 H23 0.9300 .
O24 C26 1.251(3) 2_664
O25 C26 1.250(3) .
C26 O24 1.251(3) 2_664
C26 C26 1.533(5) 2_664
O27 H27B 0.76(4) .
O27 H27A 0.74(4) .
N28 O30 1.217(3) .
N28 O29 1.224(3) .
N28 O31 1.238(3) .
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
N7 H7 O30 0.86 2.34 3.170(3) 161.3 2_666
N7 H7 O29 0.86 2.55 3.289(3) 144.2 2_666
N10 H10 O29 0.86 2.18 2.982(3) 154.3 2_666
N14 H14 O30 0.86 2.22 3.071(4) 170.3 2_676
N17 H17 O31 0.86 2.15 2.977(3) 159.9 2_676
O27 H27B O16 0.76(4) 2.00(4) 2.761(4) 175(4) 1_554
O27 H27A O31 0.74(4) 2.32(4) 3.064(4) 177(4) 2_665
