#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:25:42 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179843 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/39/7013932.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_7013932
loop_
_publ_author_name
'Jain, Sneh L.'
'Bhattacharyya, Pravat'
'Milton, Heather L.'
'Slawin, Alexandra M. Z.'
'Crayston, Joe A.'
'Woollins, J. Derek'
_publ_section_title
;
 New pyridine carboxamide ligands and their complexation to copper(II).
 X-Ray crystal structures of mono-, di, tri- and tetranuclear copper
 complexes.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              862
_journal_page_last               871
_journal_paper_doi               10.1039/b316519a
_journal_year                    2004
_chemical_formula_moiety         'C19 H16 N4 O2'
_chemical_formula_sum            'C19 H16 N4 O2'
_chemical_formula_weight         332.36
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 115.623(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.893(5)
_cell_length_b                   9.1295(18)
_cell_length_c                   16.445(3)
_cell_measurement_reflns_used    71
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      12
_cell_volume                     3369.8(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 0.9
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6961
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.725780
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0030(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2386
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0640P)²+0.4333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1906
_reflns_number_total             2386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b316519a.txt
_cod_data_source_block           H2L12
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTISCAN' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7013932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.41785(6) 0.38249(16) 0.23016(9) 0.0332(4) Uani 1 1 d . . .
C2 C 0.37034(7) 0.46019(18) 0.22219(11) 0.0294(4) Uani 1 1 d . . .
C3 C 0.36328(7) 0.5151(2) 0.29523(12) 0.0383(5) Uani 1 1 d . . .
H3A H 0.3293 0.5718 0.2867 0.046 Uiso 1 1 calc R . .
C4 C 0.40664(8) 0.4859(2) 0.38094(12) 0.0421(5) Uani 1 1 d . . .
H4A H 0.4029 0.5216 0.4325 0.051 Uiso 1 1 calc R . .
C5 C 0.45520(7) 0.4043(2) 0.39020(12) 0.0362(4) Uani 1 1 d . . .
H5A H 0.4854 0.3811 0.4484 0.043 Uiso 1 1 calc R . .
C6 C 0.45950(7) 0.35669(19) 0.31399(11) 0.0338(4) Uani 1 1 d . . .
H6A H 0.4938 0.3025 0.3211 0.041 Uiso 1 1 calc R . .
C7 C 0.32210(7) 0.48151(18) 0.12857(11) 0.0302(4) Uani 1 1 d . . .
O7 O 0.27745(5) 0.55368(13) 0.11466(8) 0.0384(3) Uani 1 1 d . . .
N8 N 0.33267(6) 0.41273(15) 0.06416(9) 0.0310(4) Uani 1 1 d D . .
H8 H 0.3702(4) 0.3587(16) 0.0846(10) 0.037(5) Uiso 1 1 d D . .
C9 C 0.29308(7) 0.4056(2) -0.02865(11) 0.0326(4) Uani 1 1 d . . .
C10 C 0.29059(7) 0.27742(19) -0.07664(10) 0.0316(4) Uani 1 1 d . . .
C11 C 0.25078(7) 0.2691(2) -0.16775(11) 0.0417(5) Uani 1 1 d . . .
H11A H 0.2494 0.1827 -0.2009 0.050 Uiso 1 1 calc R . .
C12 C 0.21303(7) 0.3857(3) -0.21081(13) 0.0509(6) Uani 1 1 d . . .
C13 C 0.21607(9) 0.5128(3) -0.16260(14) 0.0548(6) Uani 1 1 d . . .
C14 C 0.25633(8) 0.5221(2) -0.07298(12) 0.0461(5) Uani 1 1 d . . .
H14A H 0.2589 0.6104 -0.0409 0.055 Uiso 1 1 calc R . .
N15 N 0.32485(6) 0.15087(16) -0.03502(8) 0.0301(4) Uani 1 1 d D . .
H15 H 0.3040(8) 0.0567(10) -0.0460(12) 0.050(6) Uiso 1 1 d D . .
C16 C 0.38467(7) 0.14640(18) 0.01005(10) 0.0277(4) Uani 1 1 d . . .
O16 O 0.41646(5) 0.25560(13) 0.02393(7) 0.0349(3) Uani 1 1 d . . .
C17 C 0.41080(7) -0.00076(19) 0.04448(10) 0.0313(4) Uani 1 1 d . . .
N18 N 0.37283(7) -0.11003(18) 0.03047(12) 0.0501(5) Uani 1 1 d . . .
C19 C 0.39572(11) -0.2413(2) 0.06255(17) 0.0656(7) Uani 1 1 d . . .
H19A H 0.3689 -0.3207 0.0525 0.079 Uiso 1 1 calc R . .
C20 C 0.45468(11) -0.2684(2) 0.10841(15) 0.0618(6) Uani 1 1 d . . .
H20A H 0.4688 -0.3635 0.1312 0.074 Uiso 1 1 calc R . .
C21 C 0.49321(10) -0.1557(3) 0.12095(16) 0.0656(7) Uani 1 1 d . . .
H21A H 0.5350 -0.1716 0.1517 0.079 Uiso 1 1 calc R . .
C22 C 0.47133(8) -0.0184(2) 0.08888(13) 0.0487(5) Uani 1 1 d . . .
H22A H 0.4975 0.0618 0.0973 0.058 Uiso 1 1 calc R . .
C23A C 0.16923(12) 0.3878(3) -0.30465(16) 0.0423(7) Uani 0.65 1 d P . .
H23A H 0.1882 0.3573 -0.3432 0.063 Uiso 0.65 1 calc PR . .
H23B H 0.1533 0.4871 -0.3211 0.063 Uiso 0.65 1 calc PR . .
H23C H 0.1367 0.3203 -0.3128 0.063 Uiso 0.65 1 calc PR . .
C23B C 0.1671(3) 0.5986(6) -0.2200(4) 0.0470(14) Uani 0.35 1 d P . .
H23D H 0.1312 0.5674 -0.2142 0.070 Uiso 0.35 1 calc PR . .
H23E H 0.1609 0.5860 -0.2826 0.070 Uiso 0.35 1 calc PR . .
H23F H 0.1751 0.7020 -0.2030 0.070 Uiso 0.35 1 calc PR . .
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'
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
_geom_angle_publ_flag
C2 N1 C6 116.91(14) . . ?
N1 C2 C3 123.19(15) . . ?
N1 C2 C7 116.83(14) . . ?
C3 C2 C7 119.93(14) . . ?
C4 C3 C2 118.71(16) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 118.74(16) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 118.90(16) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
N1 C6 C5 123.52(15) . . ?
N1 C6 H6A 118.2 . . ?
C5 C6 H6A 118.2 . . ?
O7 C7 N8 124.87(15) . . ?
O7 C7 C2 121.34(15) . . ?
N8 C7 C2 113.78(14) . . ?
C7 N8 C9 125.85(14) . . ?
C7 N8 H8 116.5(10) . . ?
C9 N8 H8 117.6(10) . . ?
C14 C9 C10 119.15(16) . . ?
C14 C9 N8 121.68(17) . . ?
C10 C9 N8 119.17(15) . . ?
C11 C10 C9 119.30(16) . . ?
C11 C10 N15 118.13(16) . . ?
C9 C10 N15 122.48(14) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11A 119.6 . . ?
C10 C11 H11A 119.6 . . ?
C13 C12 C11 119.33(17) . . ?
C13 C12 C23A 115.2(2) . . ?
C11 C12 C23A 125.5(2) . . ?
C14 C13 C12 119.74(19) . . ?
C14 C13 C23B 134.2(3) . . ?
C12 C13 C23B 105.3(3) . . ?
C13 C14 C9 121.6(2) . . ?
C13 C14 H14A 119.2 . . ?
C9 C14 H14A 119.2 . . ?
C16 N15 C10 125.41(14) . . ?
C16 N15 H15 116.5(11) . . ?
C10 N15 H15 117.7(11) . . ?
O16 C16 N15 123.12(15) . . ?
O16 C16 C17 121.23(14) . . ?
N15 C16 C17 115.64(14) . . ?
N18 C17 C22 122.80(17) . . ?
N18 C17 C16 116.78(15) . . ?
C22 C17 C16 120.42(16) . . ?
C17 N18 C19 117.21(18) . . ?
N18 C19 C20 124.1(2) . . ?
N18 C19 H19A 118.0 . . ?
C20 C19 H19A 118.0 . . ?
C19 C20 C21 118.0(2) . . ?
C19 C20 H20A 121.0 . . ?
C21 C20 H20A 121.0 . . ?
C20 C21 C22 119.6(2) . . ?
C20 C21 H21A 120.2 . . ?
C22 C21 H21A 120.2 . . ?
C17 C22 C21 118.2(2) . . ?
C17 C22 H22A 120.9 . . ?
C21 C22 H22A 120.9 . . ?
C12 C23A H23A 109.5 . . ?
C12 C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C12 C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C13 C23B H23D 109.5 . . ?
C13 C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C13 C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.336(2) . ?
N1 C6 1.340(2) . ?
C2 C3 1.381(2) . ?
C2 C7 1.500(2) . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.371(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.374(2) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 O7 1.2254(19) . ?
C7 N8 1.352(2) . ?
N8 C9 1.416(2) . ?
N8 H8 0.9797(11) . ?
C9 C14 1.386(2) . ?
C9 C10 1.398(3) . ?
C10 C11 1.396(2) . ?
C10 N15 1.423(2) . ?
C11 C12 1.394(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(3) . ?
C12 C23A 1.454(3) . ?
C13 C14 1.381(3) . ?
C13 C23B 1.413(6) . ?
C14 H14A 0.9500 . ?
N15 C16 1.347(2) . ?
N15 H15 0.9797(11) . ?
C16 O16 1.2313(19) . ?
C16 C17 1.493(2) . ?
C17 N18 1.324(2) . ?
C17 C22 1.370(3) . ?
N18 C19 1.334(3) . ?
C19 C20 1.352(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.360(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
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
N8 H8 O16 0.9797(11) 2.048(12) 2.8355(18) 135.9(13) .
N15 H15 O7 0.9797(11) 2.103(11) 2.9672(18) 146.1(16) 7
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.9(2) . . . . ?
C6 N1 C2 C7 -176.54(14) . . . . ?
N1 C2 C3 C4 -1.5(3) . . . . ?
C7 C2 C3 C4 175.92(16) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C2 N1 C6 C5 0.7(3) . . . . ?
C4 C5 C6 N1 -1.7(3) . . . . ?
N1 C2 C7 O7 -178.54(14) . . . . ?
C3 C2 C7 O7 3.9(2) . . . . ?
N1 C2 C7 N8 2.5(2) . . . . ?
C3 C2 C7 N8 -175.11(15) . . . . ?
O7 C7 N8 C9 -3.6(3) . . . . ?
C2 C7 N8 C9 175.34(14) . . . . ?
C7 N8 C9 C14 35.8(2) . . . . ?
C7 N8 C9 C10 -143.62(16) . . . . ?
C14 C9 C10 C11 -0.6(2) . . . . ?
N8 C9 C10 C11 178.79(14) . . . . ?
C14 C9 C10 N15 -177.04(14) . . . . ?
N8 C9 C10 N15 2.4(2) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
N15 C10 C11 C12 175.54(14) . . . . ?
C10 C11 C12 C13 1.3(2) . . . . ?
C10 C11 C12 C23A -178.80(19) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C23A C12 C13 C14 -179.85(19) . . . . ?
C11 C12 C13 C23B -171.3(3) . . . . ?
C23A C12 C13 C23B 8.8(3) . . . . ?
C12 C13 C14 C9 -1.7(3) . . . . ?
C23B C13 C14 C9 166.6(4) . . . . ?
C10 C9 C14 C13 2.0(3) . . . . ?
N8 C9 C14 C13 -177.39(16) . . . . ?
C11 C10 N15 C16 125.62(16) . . . . ?
C9 C10 N15 C16 -57.9(2) . . . . ?
C10 N15 C16 O16 3.7(2) . . . . ?
C10 N15 C16 C17 -177.43(13) . . . . ?
O16 C16 C17 N18 176.37(15) . . . . ?
N15 C16 C17 N18 -2.5(2) . . . . ?
O16 C16 C17 C22 -3.1(2) . . . . ?
N15 C16 C17 C22 178.02(15) . . . . ?
C22 C17 N18 C19 0.7(3) . . . . ?
C16 C17 N18 C19 -178.71(17) . . . . ?
C17 N18 C19 C20 0.4(3) . . . . ?
N18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
N18 C17 C22 C21 -0.7(3) . . . . ?
C16 C17 C22 C21 178.70(17) . . . . ?
C20 C21 C22 C17 -0.4(3) . . . . ?
