#------------------------------------------------------------------------------
#$Date: 2015-12-09 15:14:42 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171095 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/18/7221818.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_7221818
loop_
_publ_author_name
'Ghosh, Dipankar'
'Lebedytė, Ieva'
'Yufit, Dmitry S.'
'Damodaran, Krishna K.'
'Steed, Jonathan W.'
_publ_section_title
;
 Selective gelation of N-(4-pyridyl)nicotinamide by copper(ii) salts
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              8130
_journal_paper_doi               10.1039/C5CE00901D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C26 H24 Cu N6 O6'
_chemical_formula_sum            'C26 H24 Cu N6 O6'
_chemical_formula_weight         580.05
_chemical_name_systematic
;
di(N-4-pyridylnicotinamide)copper(II)acetate 
;
_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   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-22
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-08-05 deposited with the CCDC.
2015-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                79.288(5)
_cell_angle_beta                 69.725(6)
_cell_angle_gamma                82.953(6)
_cell_formula_units_Z            1
_cell_length_a                   8.0578(6)
_cell_length_b                   8.3568(6)
_cell_length_c                   10.1944(6)
_cell_measurement_reflns_used    3243
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.4900
_cell_measurement_theta_min      2.4730
_cell_volume                     631.44(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -90.00  -64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000   90.0000 26

  2 omega  -81.00  -21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  124.0000  -32.0000 60

  3 omega -100.00   22.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337    0.0000  -30.0000 122

  4 omega   60.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000 -180.0000 31

  5 omega  -19.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -180.0000 90

  6 omega    0.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -60.0000 99

  7 omega    3.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   38.0000 -150.0000 94
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0428552000
_diffrn_orient_matrix_UB_12      0.0741789000
_diffrn_orient_matrix_UB_13      0.0228330000
_diffrn_orient_matrix_UB_21      0.0265067000
_diffrn_orient_matrix_UB_22      0.0397144000
_diffrn_orient_matrix_UB_23      -0.0712078000
_diffrn_orient_matrix_UB_31      -0.0793870000
_diffrn_orient_matrix_UB_32      -0.0203015000
_diffrn_orient_matrix_UB_33      -0.0065849000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0416
_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            7769
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.16
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             299
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0348
_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)+(0.0300P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                3339
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce00901d2.cif
_cod_data_source_block           Complex1
_cod_depositor_comments
'Adding full bibliography for 7221817--7221820.cif.'
_cod_original_cell_volume        631.44(7)
_cod_database_code               7221818
_chemical_oxdiff_formula         'C26 H26 Cu1 N6 O4'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.0000 0.0000 0.5000 0.01534(8) Uani 1 d 2 S T P
O1 O 0.25188(19) 0.1760(2) 1.04336(15) 0.0456(4) Uani 1 d 1 . . .
O2 O 0.00501(14) 0.23201(13) 0.40396(12) 0.0184(2) Uani 1 d 1 . . .
O3 O -0.21288(14) 0.21793(14) 0.60889(13) 0.0216(2) Uani 1 d 1 . . .
N1 N 0.15311(17) 0.04691(15) 0.60262(14) 0.0165(3) Uani 1 d 1 . . .
N2 N 0.45146(18) 0.19230(17) 0.82067(15) 0.0183(3) Uani 1 d 1 . . .
N3 N 0.5719(2) 0.3562(2) 1.20911(17) 0.0326(4) Uani 1 d 1 . . .
C1 C 0.3035(2) 0.12400(19) 0.53538(17) 0.0176(3) Uani 1 d 1 . . .
C2 C 0.4038(2) 0.17089(19) 0.60543(17) 0.0170(3) Uani 1 d 1 . . .
C3 C 0.3477(2) 0.14046(18) 0.75298(17) 0.0163(3) Uani 1 d 1 . . .
C4 C 0.1926(2) 0.0586(2) 0.82335(19) 0.0239(3) Uani 1 d 1 . . .
C5 C 0.1019(2) 0.0136(2) 0.74387(18) 0.0229(3) Uani 1 d 1 . . .
C6 C 0.3987(2) 0.2074(2) 0.96079(18) 0.0233(3) Uani 1 d 1 . . .
C7 C 0.5314(2) 0.2682(2) 1.01021(17) 0.0214(3) Uani 1 d 1 . . .
C8 C 0.7085(2) 0.2897(2) 0.93028(19) 0.0263(4) Uani 1 d 1 . . .
C9 C 0.8152(3) 0.3444(3) 0.9920(2) 0.0326(4) Uani 1 d 1 . . .
C10 C 0.7421(3) 0.3741(3) 1.1303(2) 0.0334(4) Uani 1 d 1 . . .
C11 C 0.4699(3) 0.3040(2) 1.14816(19) 0.0259(4) Uani 1 d 1 . . .
C12 C -0.1266(2) 0.29720(19) 0.49275(18) 0.0184(3) Uani 1 d 1 . . .
C13 C -0.1828(3) 0.4731(2) 0.4546(2) 0.0308(4) Uani 1 d 1 . . .
H1 H 0.339(2) 0.150(2) 0.435(2) 0.019(5) Uiso 1 d 1 . . .
H2 H 0.553(3) 0.217(2) 0.763(2) 0.028(5) Uiso 1 d 1 . . .
H2A H 0.506(3) 0.229(2) 0.551(2) 0.022(5) Uiso 1 d 1 . . .
H4 H 0.152(2) 0.031(2) 0.919(2) 0.023(5) Uiso 1 d 1 . . .
H5 H -0.004(3) -0.042(2) 0.791(2) 0.027(5) Uiso 1 d 1 . . .
H8 H 0.760(3) 0.263(3) 0.837(2) 0.034(6) Uiso 1 d 1 . . .
H9 H 0.940(3) 0.354(3) 0.942(3) 0.047(7) Uiso 1 d 1 . . .
H10 H 0.810(3) 0.408(3) 1.175(3) 0.047(7) Uiso 1 d 1 . . .
H11 H 0.347(3) 0.294(3) 1.206(2) 0.040(6) Uiso 1 d 1 . . .
H13A H -0.092(3) 0.530(3) 0.377(3) 0.043(6) Uiso 1 d 1 . . .
H13B H -0.281(3) 0.478(3) 0.425(3) 0.045(7) Uiso 1 d 1 . . .
H13C H -0.222(3) 0.524(3) 0.535(3) 0.061(8) Uiso 1 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 0.0033 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'
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
O2 Cu1 O2 180 2_556 .
N1 Cu1 O2 89.75(5) 2_556 .
N1 Cu1 O2 89.75(5) . 2_556
N1 Cu1 O2 90.25(5) . .
N1 Cu1 O2 90.25(5) 2_556 2_556
N1 Cu1 N1 180 2_556 .
C12 O2 Cu1 100.81(10) . .
C1 N1 Cu1 121.88(11) . .
C5 N1 Cu1 120.42(10) . .
C5 N1 C1 117.50(13) . .
C3 N2 H2 111.4(14) . .
C6 N2 C3 125.73(14) . .
C6 N2 H2 122.8(14) . .
C10 N3 C11 116.51(16) . .
N1 C1 C2 122.99(15) . .
N1 C1 H1 117.7(11) . .
C2 C1 H1 119.3(11) . .
C1 C2 C3 119.52(14) . .
C1 C2 H2A 118.2(12) . .
C3 C2 H2A 122.2(12) . .
C2 C3 N2 117.94(14) . .
C2 C3 C4 117.72(14) . .
C4 C3 N2 124.34(14) . .
C3 C4 H4 121.8(12) . .
C5 C4 C3 118.70(16) . .
C5 C4 H4 119.4(12) . .
N1 C5 C4 123.53(15) . .
N1 C5 H5 117.3(12) . .
C4 C5 H5 119.1(12) . .
O1 C6 N2 123.05(15) . .
O1 C6 C7 120.30(15) . .
N2 C6 C7 116.64(14) . .
C8 C7 C6 125.26(15) . .
C8 C7 C11 118.32(15) . .
C11 C7 C6 116.42(15) . .
C7 C8 H8 122.2(12) . .
C9 C8 C7 118.34(17) . .
C9 C8 H8 119.4(12) . .
C8 C9 H9 120.4(14) . .
C10 C9 C8 118.92(18) . .
C10 C9 H9 120.5(14) . .
N3 C10 C9 124.04(16) . .
N3 C10 H10 115.1(15) . .
C9 C10 H10 120.8(16) . .
N3 C11 C7 123.85(17) . .
N3 C11 H11 115.4(13) . .
C7 C11 H11 120.7(13) . .
O2 C12 C13 118.62(16) . .
O3 C12 O2 121.89(14) . .
O3 C12 C13 119.46(16) . .
C12 C13 H13A 112.4(14) . .
C12 C13 H13B 108.9(14) . .
C12 C13 H13C 109.8(17) . .
H13A C13 H13B 107(2) . .
H13A C13 H13C 113(2) . .
H13B C13 H13C 106(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 2.0013(11) 2_556
Cu1 O2 2.0013(11) .
Cu1 N1 1.9839(12) 2_556
Cu1 N1 1.9839(12) .
O1 C6 1.217(2) .
O2 C12 1.2715(19) .
O3 C12 1.255(2) .
N1 C1 1.343(2) .
N1 C5 1.337(2) .
N2 C3 1.4012(18) .
N2 C6 1.368(2) .
N2 H2 0.85(2) .
N3 C10 1.338(3) .
N3 C11 1.340(2) .
C1 C2 1.378(2) .
C1 H1 0.952(19) .
C2 C3 1.395(2) .
C2 H2A 0.95(2) .
C3 C4 1.396(2) .
C4 C5 1.387(2) .
C4 H4 0.91(2) .
C5 H5 0.95(2) .
C6 C7 1.502(2) .
C7 C8 1.391(2) .
C7 C11 1.396(2) .
C8 C9 1.386(2) .
C8 H8 0.96(2) .
C9 C10 1.384(3) .
C9 H9 0.96(2) .
C10 H10 0.92(2) .
C11 H11 0.97(2) .
C12 C13 1.504(2) .
C13 H13A 0.97(2) .
C13 H13B 0.93(2) .
C13 H13C 0.93(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
N2 H2 O3 0.85(2) 1.99(2) 2.8188(18) 164.2(19) 1_655
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
C2 C3 N2 C6 164.03(16)
C3 N2 C6 O1 0.2(3)
C4 C3 N2 C6 -16.7(3)
C7 C6 N2 C3 -178.96(14)
C8 C7 C6 O1 172.07(19)
C8 C7 C6 N2 -8.8(3)
C11 C7 C6 O1 -7.4(3)
C11 C7 C6 N2 171.79(15)
