#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:02:04 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179552 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/21/4502119.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_4502119
loop_
_publ_author_name
'Adarsh, N. N.'
'Sahoo, Pathik'
'Dastidar, Parthasarathi'
_publ_section_title
;
 Is a Crystal Engineering Approach Useful in Designing Metallogels? A Case
 Study
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4976
_journal_paper_doi               10.1021/cg101078f
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C20 H18 Cu N4 O8'
_chemical_formula_weight         505.92
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.464(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.151(2)
_cell_length_b                   7.9995(13)
_cell_length_c                   18.864(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1975.5(5)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker Apex II'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Mercury 2.3, Ortep3v2'
_computing_publication_material  Shelxtl-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker CCD Area Detector'
_diffrn_measurement_method       'Phi-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  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15192
_diffrn_reflns_theta_full        23.02
_diffrn_reflns_theta_max         23.02
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.166
_exptl_absorpt_correction_T_max  0.9125
_exptl_absorpt_correction_T_min  0.7360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0397
_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)+(0.0601P)²+1.2031P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2176
_reflns_number_total             2750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg101078f_si_002.cif
_cod_data_source_block           1a
_cod_original_cell_volume        1975.4(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4502119
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.61652(4) 0.27989(7) 0.83122(2) 0.0285(2) Uani 1 1 d .
N1 N 0.5003(2) 0.3202(4) 0.89101(17) 0.0278(8) Uani 1 1 d .
C2 C 0.4477(3) 0.4651(5) 0.8852(2) 0.0303(10) Uani 1 1 d .
H2 H 0.4583 0.5381 0.8483 0.036 Uiso 1 1 calc R
C3 C 0.3777(3) 0.5080(5) 0.9334(2) 0.0254(9) Uani 1 1 d .
C4 C 0.3634(3) 0.3971(5) 0.9877(2) 0.0338(11) Uani 1 1 d .
H4 H 0.3175 0.4226 1.0208 0.041 Uiso 1 1 calc R
C5 C 0.4164(4) 0.2505(5) 0.9930(2) 0.0378(12) Uani 1 1 d .
H5 H 0.4067 0.1747 1.0292 0.045 Uiso 1 1 calc R
C6 C 0.4850(3) 0.2164(5) 0.9435(2) 0.0333(11) Uani 1 1 d .
H6 H 0.5216 0.1168 0.9473 0.040 Uiso 1 1 calc R
N7 N 0.3244(2) 0.6597(4) 0.93144(17) 0.0283(8) Uani 1 1 d .
H7 H 0.2945 0.6835 0.9688 0.034 Uiso 1 1 calc R
C8 C 0.3140(3) 0.7738(5) 0.8780(2) 0.0306(10) Uani 1 1 d .
O9 O 0.3555(3) 0.7605(4) 0.82329(17) 0.0502(10) Uani 1 1 d .
C10 C 0.2438(3) 0.9171(5) 0.8890(2) 0.0274(10) Uani 1 1 d .
C11 C 0.1967(3) 0.9973(5) 0.8290(2) 0.0321(10) Uani 1 1 d .
H11 H 0.2146 0.9690 0.7840 0.039 Uiso 1 1 calc R
C12 C 0.1242(3) 1.1177(6) 0.8359(2) 0.0351(11) Uani 1 1 d .
H12 H 0.0919 1.1685 0.7955 0.042 Uiso 1 1 calc R
C13 C 0.0985(3) 1.1644(5) 0.9029(2) 0.0303(10) Uani 1 1 d .
H13 H 0.0480 1.2441 0.9071 0.036 Uiso 1 1 calc R
C14 C 0.1479(3) 1.0924(5) 0.9631(2) 0.0262(10) Uani 1 1 d .
C15 C 0.2197(3) 0.9669(5) 0.9554(2) 0.0274(10) Uani 1 1 d .
H15 H 0.2518 0.9158 0.9957 0.033 Uiso 1 1 calc R
C16 C 0.1294(3) 1.1369(5) 1.0376(2) 0.0328(10) Uani 1 1 d .
O17 O 0.1907(3) 1.0956(6) 1.08699(17) 0.0765(14) Uani 1 1 d .
N18 N 0.0439(3) 1.2214(4) 1.04847(17) 0.0277(8) Uani 1 1 d .
H18 H 0.0040 1.2472 1.0113 0.033 Uiso 1 1 calc R
C19 C 0.0130(3) 1.2718(5) 1.1144(2) 0.0246(9) Uani 1 1 d .
C20 C -0.0682(3) 1.3825(5) 1.1145(2) 0.0282(10) Uani 1 1 d .
H20 H -0.0997 1.4238 1.0719 0.034 Uiso 1 1 calc R
C21 C -0.1019(3) 1.4307(5) 1.1785(2) 0.0302(10) Uani 1 1 d .
H21 H -0.1574 1.5026 1.1794 0.036 Uiso 1 1 calc R
C22 C -0.0524(3) 1.3709(5) 1.2407(2) 0.0294(10) Uani 1 1 d .
H22 H -0.0750 1.4036 1.2839 0.035 Uiso 1 1 calc R
N23 N 0.0271(3) 1.2676(4) 1.24127(17) 0.0264(8) Uani 1 1 d .
C24 C 0.0587(3) 1.2184(5) 1.1797(2) 0.0280(10) Uani 1 1 d .
H24 H 0.1138 1.1452 1.1805 0.034 Uiso 1 1 calc R
O25 O 0.7400(2) 0.2670(4) 0.78191(15) 0.0364(8) Uani 1 1 d .
C26 C 0.8217(3) 0.3025(6) 0.8210(2) 0.0327(10) Uani 1 1 d .
O27 O 0.9055(2) 0.3210(5) 0.79972(17) 0.0599(10) Uani 1 1 d .
C28 C 0.8071(3) 0.3196(5) 0.9014(2) 0.0317(10) Uani 1 1 d .
O29 O 0.7149(2) 0.3059(4) 0.91619(14) 0.0320(7) Uani 1 1 d .
O30 O 0.8799(2) 0.3443(4) 0.94523(15) 0.0448(8) Uani 1 1 d .
O31 O 0.6175(2) -0.0258(4) 0.84826(16) 0.0459(8) Uani 1 1 d .
O32 O 0.6403(3) 0.5868(5) 0.8164(2) 0.0696(11) 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
O25 Cu1 O29 83.18(11) . .
O25 Cu1 N23 91.96(13) . 4_675
O29 Cu1 N23 173.33(12) . 4_675
O25 Cu1 N1 171.33(13) . .
O29 Cu1 N1 90.12(12) . .
N23 Cu1 N1 95.14(13) 4_675 .
C6 N1 C2 119.1(3) . .
C6 N1 Cu1 119.8(3) . .
C2 N1 Cu1 120.3(3) . .
N1 C2 C3 121.5(4) . .
N1 C2 H2 119.2 . .
C3 C2 H2 119.2 . .
C4 C3 C2 118.0(4) . .
C4 C3 N7 118.2(3) . .
C2 C3 N7 123.7(4) . .
C5 C4 C3 120.1(4) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 118.7(4) . .
C4 C5 H5 120.6 . .
C6 C5 H5 120.6 . .
N1 C6 C5 122.4(4) . .
N1 C6 H6 118.8 . .
C5 C6 H6 118.8 . .
C8 N7 C3 128.1(3) . .
C8 N7 H7 116.0 . .
C3 N7 H7 116.0 . .
O9 C8 N7 123.3(4) . .
O9 C8 C10 121.1(4) . .
N7 C8 C10 115.5(3) . .
C15 C10 C11 118.7(4) . .
C15 C10 C8 123.0(4) . .
C11 C10 C8 118.1(4) . .
C12 C11 C10 120.4(4) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C13 120.4(4) . .
C11 C12 H12 119.8 . .
C13 C12 H12 119.8 . .
C14 C13 C12 120.0(4) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C15 119.0(4) . .
C13 C14 C16 124.7(4) . .
C15 C14 C16 116.3(3) . .
C10 C15 C14 121.3(4) . .
C10 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
O17 C16 N18 121.4(4) . .
O17 C16 C14 120.0(4) . .
N18 C16 C14 118.5(4) . .
C16 N18 C19 126.6(3) . .
C16 N18 H18 116.7 . .
C19 N18 H18 116.7 . .
C24 C19 C20 117.6(4) . .
C24 C19 N18 124.2(4) . .
C20 C19 N18 118.2(3) . .
C21 C20 C19 119.5(4) . .
C21 C20 H20 120.3 . .
C19 C20 H20 120.3 . .
C22 C21 C20 119.0(4) . .
C22 C21 H21 120.5 . .
C20 C21 H21 120.5 . .
N23 C22 C21 122.0(4) . .
N23 C22 H22 119.0 . .
C21 C22 H22 119.0 . .
C24 N23 C22 119.2(3) . .
C24 N23 Cu1 118.4(3) . 4_576
C22 N23 Cu1 121.3(3) . 4_576
N23 C24 C19 122.7(4) . .
N23 C24 H24 118.7 . .
C19 C24 H24 118.7 . .
C26 O25 Cu1 113.9(3) . .
O27 C26 O25 125.1(4) . .
O27 C26 C28 120.8(4) . .
O25 C26 C28 114.1(4) . .
O30 C28 O29 124.6(4) . .
O30 C28 C26 120.9(4) . .
O29 C28 C26 114.5(4) . .
C28 O29 Cu1 113.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O25 1.950(3) .
Cu1 O29 1.973(3) .
Cu1 N23 2.006(3) 4_675
Cu1 N1 2.010(3) .
N1 C6 1.322(5) .
N1 C2 1.349(5) .
C2 C3 1.397(5) .
C2 H2 0.9300 .
C3 C4 1.382(6) .
C3 N7 1.400(5) .
C4 C5 1.363(6) .
C4 H4 0.9300 .
C5 C6 1.387(6) .
C5 H5 0.9300 .
C6 H6 0.9300 .
N7 C8 1.358(5) .
N7 H7 0.8600 .
C8 O9 1.216(5) .
C8 C10 1.499(6) .
C10 C15 1.379(5) .
C10 C11 1.394(6) .
C11 C12 1.370(6) .
C11 H11 0.9300 .
C12 C13 1.390(6) .
C12 H12 0.9300 .
C13 C14 1.379(6) .
C13 H13 0.9300 .
C14 C15 1.395(5) .
C14 C16 1.492(5) .
C15 H15 0.9300 .
C16 O17 1.218(5) .
C16 N18 1.345(5) .
N18 C19 1.404(5) .
N18 H18 0.8600 .
C19 C24 1.386(5) .
C19 C20 1.388(5) .
C20 C21 1.379(5) .
C20 H20 0.9300 .
C21 C22 1.374(6) .
C21 H21 0.9300 .
C22 N23 1.332(5) .
C22 H22 0.9300 .
N23 C24 1.329(5) .
N23 Cu1 2.006(3) 4_576
C24 H24 0.9300 .
O25 C26 1.275(5) .
C26 O27 1.218(5) .
C26 C28 1.552(6) .
C28 O30 1.221(5) .
C28 O29 1.274(5) .
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 O29 0.86 2.19 2.982(4) 153.5 3_667
N18 H18 O30 0.86 2.10 2.934(4) 161.6 1_465
