#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/67/2236789.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236789
loop_
_publ_author_name
'Kunnath, Roji J.'
'Prathapachandra Kurup, M.R.'
'Ng, Seik Weng'
_publ_section_title
;
 (Cyanato-κN){1-[(E)-phenyl(pyridin-2-yl-κN)methylidene]semicarbazidato-κ²N¹,O}copper(II)
;
_journal_coeditor_code           ZS2226
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1180
_journal_paper_doi               10.1107/S1600536812035386
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Cu (C13 H11 N4 O) (N C O)]'
_chemical_formula_moiety         'C14 H11 Cu N5 O2'
_chemical_formula_sum            'C14 H11 Cu N5 O2'
_chemical_formula_weight         344.82
_chemical_name_systematic
;
(Cyanato-κN){1-[(E)-phenyl(pyridin-2-yl-
κN)methylidene]semicarbazidato-κ²N¹,O}copper(II)
;
_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                 96.7467(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.76010(10)
_cell_length_b                   7.67320(10)
_cell_length_c                   20.0819(3)
_cell_measurement_reflns_used    838
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3324
_cell_measurement_theta_min      2.4418
_cell_volume                     1340.52(3)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11886
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  0.7345
_exptl_absorpt_correction_T_min  0.6383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.465
_refine_ls_extinction_coef       0.0221(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.5121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                2728
_reflns_number_total             3069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2226.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2236789
_cod_database_fobs_code          2236789
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cu Cu1 0.31070(2) 0.50325(3) 0.506177(10) 0.03203(12) Uani d . 1 1
O O1 0.28257(17) 0.3049(2) 0.56285(6) 0.0473(4) Uani d . 1 1
O O2 0.5831(2) 0.6387(3) 0.67349(8) 0.0696(6) Uani d . 1 1
N N1 0.26412(17) 0.6848(2) 0.43675(7) 0.0323(3) Uani d . 1 1
N N2 0.13987(16) 0.38948(19) 0.45304(7) 0.0287(3) Uani d . 1 1
N N3 0.09476(17) 0.2331(2) 0.47511(7) 0.0332(3) Uani d . 1 1
N N4 0.1503(3) 0.0571(3) 0.56674(9) 0.0526(5) Uani d D 1 1
H H41 0.078(2) -0.018(3) 0.5525(15) 0.057(8) Uiso d D 1 1
H H42 0.196(3) 0.034(4) 0.6065(8) 0.059(8) Uiso d D 1 1
N N5 0.47729(18) 0.6213(2) 0.56268(8) 0.0391(4) Uani d . 1 1
C C1 0.3226(2) 0.8437(3) 0.43590(10) 0.0425(4) Uani d . 1 1
H H1 0.3972 0.8773 0.4703 0.051 Uiso calc R 1 1
C C2 0.2763(3) 0.9611(3) 0.38550(13) 0.0480(5) Uani d . 1 1
H H2 0.3178 1.0727 0.3862 0.058 Uiso calc R 1 1
C C3 0.1682(2) 0.9104(3) 0.33440(11) 0.0448(5) Uani d . 1 1
H H3 0.1354 0.9875 0.2999 0.054 Uiso calc R 1 1
C C4 0.1084(2) 0.7441(3) 0.33435(9) 0.0383(4) Uani d . 1 1
H H4 0.0364 0.7071 0.2995 0.046 Uiso calc R 1 1
C C5 0.15699(19) 0.6327(2) 0.38691(8) 0.0299(3) Uani d . 1 1
C C6 0.09472(19) 0.4563(3) 0.39498(8) 0.0289(3) Uani d . 1 1
C C7 -0.00451(19) 0.3697(2) 0.34034(8) 0.0295(3) Uani d . 1 1
C C8 0.0435(2) 0.3596(3) 0.27703(9) 0.0373(4) Uani d . 1 1
H H8 0.1360 0.4106 0.2691 0.045 Uiso calc R 1 1
C C9 -0.0453(2) 0.2744(3) 0.22558(9) 0.0438(5) Uani d . 1 1
H H9 -0.0119 0.2674 0.1834 0.053 Uiso calc R 1 1
C C10 -0.1826(2) 0.2003(3) 0.23667(10) 0.0453(5) Uani d . 1 1
H H10 -0.2419 0.1424 0.2021 0.054 Uiso calc R 1 1
C C11 -0.2324(2) 0.2114(3) 0.29881(11) 0.0438(5) Uani d . 1 1
H H11 -0.3263 0.1626 0.3060 0.053 Uiso calc R 1 1
C C12 -0.1440(2) 0.2947(3) 0.35081(9) 0.0351(4) Uani d . 1 1
H H12 -0.1779 0.3006 0.3929 0.042 Uiso calc R 1 1
C C13 0.1784(2) 0.2042(3) 0.53522(8) 0.0369(4) Uani d . 1 1
C C14 0.5253(2) 0.6252(3) 0.61718(10) 0.0396(4) Uani d . 1 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'
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_site_symmetry_3
_geom_angle
O1 Cu1 N2 . 79.99(6)
O1 Cu1 N5 . 99.25(6)
N2 Cu1 N5 . 177.52(6)
O1 Cu1 N1 . 159.83(6)
N2 Cu1 N1 . 81.22(6)
N5 Cu1 N1 . 99.23(7)
O1 Cu1 N5 3_666 99.82(6)
N2 Cu1 N5 3_666 95.41(6)
N5 Cu1 N5 3_666 87.05(6)
N1 Cu1 N5 3_666 89.15(6)
C13 O1 Cu1 . 110.84(11)
C1 N1 C5 . 119.97(16)
C1 N1 Cu1 . 127.54(13)
C5 N1 Cu1 . 112.47(12)
C6 N2 N3 . 125.23(14)
C6 N2 Cu1 . 116.88(12)
N3 N2 Cu1 . 117.03(10)
N2 N3 C13 . 106.76(14)
C13 N4 H41 . 124(2)
C13 N4 H42 . 121(2)
H41 N4 H42 . 114(3)
C14 N5 Cu1 . 137.89(16)
N1 C1 C2 . 121.99(19)
N1 C1 H1 . 119.0
C2 C1 H1 . 119.0
C3 C2 C1 . 118.8(2)
C3 C2 H2 . 120.6
C1 C2 H2 . 120.6
C2 C3 C4 . 119.53(19)
C2 C3 H3 . 120.2
C4 C3 H3 . 120.2
C3 C4 C5 . 119.16(18)
C3 C4 H4 . 120.4
C5 C4 H4 . 120.4
N1 C5 C4 . 120.48(17)
N1 C5 C6 . 115.08(15)
C4 C5 C6 . 124.40(16)
N2 C6 C7 . 125.67(17)
N2 C6 C5 . 112.66(15)
C7 C6 C5 . 121.65(15)
C8 C7 C12 . 118.85(16)
C8 C7 C6 . 119.40(16)
C12 C7 C6 . 121.74(16)
C9 C8 C7 . 120.43(18)
C9 C8 H8 . 119.8
C7 C8 H8 . 119.8
C10 C9 C8 . 120.13(19)
C10 C9 H9 . 119.9
C8 C9 H9 . 119.9
C9 C10 C11 . 120.02(17)
C9 C10 H10 . 120.0
C11 C10 H10 . 120.0
C10 C11 C12 . 120.38(18)
C10 C11 H11 . 119.8
C12 C11 H11 . 119.8
C11 C12 C7 . 120.18(18)
C11 C12 H12 . 119.9
C7 C12 H12 . 119.9
O1 C13 N4 . 118.09(17)
O1 C13 N3 . 125.08(17)
N4 C13 N3 . 116.82(17)
N5 C14 O2 . 175.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O1 . 1.9335(14)
Cu1 N2 . 1.9404(14)
Cu1 N5 . 1.9618(16)
Cu1 N1 . 1.9790(15)
Cu1 N5 3_666 2.6225(17)
O1 C13 . 1.272(2)
O2 C14 . 1.188(2)
N1 C1 . 1.324(2)
N1 C5 . 1.349(2)
N2 C6 . 1.293(2)
N2 N3 . 1.354(2)
N3 C13 . 1.355(2)
N4 C13 . 1.331(3)
N4 H41 . 0.876(10)
N4 H42 . 0.869(10)
N5 C14 . 1.126(2)
C1 C2 . 1.380(3)
C1 H1 . 0.9300
C2 C3 . 1.368(3)
C2 H2 . 0.9300
C3 C4 . 1.379(3)
C3 H3 . 0.9300
C4 C5 . 1.385(2)
C4 H4 . 0.9300
C5 C6 . 1.475(2)
C6 C7 . 1.475(2)
C7 C8 . 1.388(2)
C7 C12 . 1.388(2)
C8 C9 . 1.382(3)
C8 H8 . 0.9300
C9 C10 . 1.372(3)
C9 H9 . 0.9300
C10 C11 . 1.372(3)
C10 H10 . 0.9300
C11 C12 . 1.382(3)
C11 H11 . 0.9300
C12 H12 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H41 N3 3_556 0.880(10) 2.270(10) 3.139(2) 173(3)
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_site_symmetry_1
_geom_torsion
N2 Cu1 O1 C13 . 3.55(14)
N5 Cu1 O1 C13 . -178.85(14)
N1 Cu1 O1 C13 . 25.1(3)
N5 Cu1 O1 C13 3_666 -90.27(14)
O1 Cu1 N1 C1 . 150.16(19)
N2 Cu1 N1 C1 . 171.58(18)
N5 Cu1 N1 C1 . -5.94(18)
N5 Cu1 N1 C1 3_666 -92.81(17)
O1 Cu1 N1 C5 . -28.2(3)
N2 Cu1 N1 C5 . -6.80(12)
N5 Cu1 N1 C5 . 175.67(12)
N5 Cu1 N1 C5 3_666 88.80(12)
O1 Cu1 N2 C6 . -175.17(14)
N1 Cu1 N2 C6 . 12.18(13)
N5 Cu1 N2 C6 3_666 -76.12(14)
O1 Cu1 N2 N3 . -5.25(12)
N1 Cu1 N2 N3 . -177.90(13)
N5 Cu1 N2 N3 3_666 93.80(12)
C6 N2 N3 C13 . 174.42(17)
Cu1 N2 N3 C13 . 5.43(18)
O1 Cu1 N5 C14 . -22.4(3)
N1 Cu1 N5 C14 . 149.4(2)
N5 Cu1 N5 C14 3_666 -121.9(3)
C5 N1 C1 C2 . 0.7(3)
Cu1 N1 C1 C2 . -177.57(16)
N1 C1 C2 C3 . -1.0(3)
C1 C2 C3 C4 . 0.0(3)
C2 C3 C4 C5 . 1.3(3)
C1 N1 C5 C4 . 0.6(3)
Cu1 N1 C5 C4 . 179.09(14)
C1 N1 C5 C6 . -177.08(16)
Cu1 N1 C5 C6 . 1.45(19)
C3 C4 C5 N1 . -1.5(3)
C3 C4 C5 C6 . 175.87(18)
N3 N2 C6 C7 . -4.9(3)
Cu1 N2 C6 C7 . 164.10(13)
N3 N2 C6 C5 . 176.72(15)
Cu1 N2 C6 C5 . -14.28(19)
N1 C5 C6 N2 . 8.2(2)
C4 C5 C6 N2 . -169.37(17)
N1 C5 C6 C7 . -170.28(15)
C4 C5 C6 C7 . 12.2(3)
N2 C6 C7 C8 . -126.9(2)
C5 C6 C7 C8 . 51.4(2)
N2 C6 C7 C12 . 51.9(3)
C5 C6 C7 C12 . -129.86(18)
C12 C7 C8 C9 . -0.8(3)
C6 C7 C8 C9 . 178.00(19)
C7 C8 C9 C10 . 0.5(3)
C8 C9 C10 C11 . 0.4(3)
C9 C10 C11 C12 . -1.0(3)
C10 C11 C12 C7 . 0.8(3)
C8 C7 C12 C11 . 0.2(3)
C6 C7 C12 C11 . -178.62(18)
Cu1 O1 C13 N4 . 176.97(17)
Cu1 O1 C13 N3 . -1.7(3)
N2 N3 C13 O1 . -2.4(3)
N2 N3 C13 N4 . 178.93(19)
