#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/81/2218163.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_2218163
loop_
_publ_author_name
'Qiu, Zhanglei'
'Li, Lianzhi'
'Liu, Yan'
'Xu, Tao'
'Wang, Daqi'
_publ_section_title
(2,2'-Bipyridine-κ²N,N')[N-(2-oxido-1-naphthylidene)threoninato-κ³O¹,N,O²]copper(II)
_journal_coeditor_code           HY2129
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m745
_journal_page_last               m746
_journal_paper_doi               10.1107/S1600536808012191
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C15 H13 N O4) (C10 H8 N2)]'
_chemical_formula_moiety         'C25 H21 Cu N3 O4'
_chemical_formula_sum            'C25 H21 Cu N3 O4'
_chemical_formula_weight         490.99
_chemical_name_systematic
;
(2,2'-Bipyridine-κ²N,N')[N-(2-oxido-1-
naphthylidene)threoninato-κ³O¹,N,O²]copper(II)
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.955(2)
_cell_length_b                   12.180(3)
_cell_length_c                   18.438(4)
_cell_measurement_reflns_used    5604
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.09
_cell_measurement_theta_min      2.325
_cell_volume                     2235.6(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14242
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.014
_exptl_absorpt_correction_T_max  0.8545
_exptl_absorpt_correction_T_min  0.7574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1012
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.540
_refine_ls_abs_structure_details 'Flack (1983), 2229 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.005(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         5278
_refine_ls_number_restraints     492
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0337
_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)+(0.0472P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0885
_reflns_number_gt                4243
_reflns_number_total             5278
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2129.cif
_cod_data_source_block           I
_cod_database_code               2218163
_cod_database_fobs_code          2218163
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
Cu Cu1 0.32501(3) 1.00767(2) 0.977106(17) 0.03806(10) Uani d . 1
N N1 0.1622(2) 1.08781(15) 0.95744(11) 0.0313(4) Uani d . 1
N N2 0.2672(3) 0.89079(19) 1.06492(15) 0.0491(6) Uani d . 1
N N3 0.5005(2) 0.93672(19) 1.00252(14) 0.0480(6) Uani d . 1
O O4 0.3191(2) 0.93362(17) 0.88490(11) 0.0498(5) Uani d . 1
O O2 0.29386(19) 1.31490(16) 1.05070(12) 0.0512(5) Uani d . 1
O O1 0.37076(18) 1.14608(15) 1.03256(11) 0.0424(4) Uani d . 1
O O3 -0.05190(19) 1.07490(16) 1.05400(12) 0.0474(5) Uani d . 1
H H3 -0.0961 1.1082 1.0236 0.071 Uiso calc R 1
C C1 0.2783(3) 1.2178(2) 1.03223(14) 0.0371(6) Uani d U 1
C C2 0.1394(3) 1.17825(19) 1.00763(13) 0.0319(5) Uani d U 1
H H28 0.0912 1.2379 0.9832 0.038 Uiso calc R 1
C C3 0.0596(3) 1.1395(2) 1.07501(15) 0.0368(6) Uani d U 1
H H29 0.1194 1.0925 1.1037 0.044 Uiso calc R 1
C C4 0.0177(3) 1.2351(3) 1.12313(16) 0.0510(7) Uani d U 1
H H21A -0.0285 1.2076 1.1651 0.077 Uiso calc R 1
H H21B -0.0409 1.2830 1.0965 0.077 Uiso calc R 1
H H21C 0.0960 1.2750 1.1382 0.077 Uiso calc R 1
C C5 0.0856(2) 1.0765(2) 0.90139(14) 0.0325(5) Uani d U 1
H H11 0.0125 1.1237 0.8978 0.039 Uiso calc R 1
C C6 0.1028(2) 0.9982(2) 0.84450(12) 0.0363(5) Uani d U 1
C C7 0.2228(3) 0.9366(2) 0.83774(15) 0.0415(6) Uani d U 1
C C8 0.2402(3) 0.8722(3) 0.77391(16) 0.0545(8) Uani d U 1
H H18 0.3199 0.8335 0.7678 0.065 Uiso calc R 1
C C9 0.1453(4) 0.8654(3) 0.72205(16) 0.0560(8) Uani d U 1
H H19 0.1615 0.8224 0.6813 0.067 Uiso calc R 1
C C10 0.0215(3) 0.9221(2) 0.72803(15) 0.0452(6) Uani d U 1
C C11 -0.0016(3) 0.9893(2) 0.78988(13) 0.0397(6) Uani d U 1
C C12 -0.1269(3) 1.0408(2) 0.79527(17) 0.0495(7) Uani d U 1
H H27 -0.1453 1.0845 0.8354 0.059 Uiso calc R 1
C C13 -0.2234(4) 1.0284(3) 0.74247(19) 0.0588(8) Uani d U 1
H H26 -0.3055 1.0640 0.7475 0.071 Uiso calc R 1
C C14 -0.2000(4) 0.9635(3) 0.68174(18) 0.0621(9) Uani d U 1
H H25 -0.2659 0.9556 0.6464 0.074 Uiso calc R 1
C C15 -0.0795(4) 0.9115(3) 0.67446(17) 0.0572(8) Uani d U 1
H H15 -0.0634 0.8685 0.6337 0.069 Uiso calc R 1
C C16 0.1466(4) 0.8711(3) 1.0941(2) 0.0660(9) Uani d U 1
H H17 0.0701 0.8976 1.0710 0.079 Uiso calc R 1
C C17 0.1333(6) 0.8119(3) 1.1577(3) 0.0965(13) Uani d U 1
H H22 0.0488 0.7999 1.1777 0.116 Uiso calc R 1
C C18 0.2463(6) 0.7710(4) 1.1912(3) 0.1063(14) Uani d U 1
H H36 0.2387 0.7302 1.2336 0.128 Uiso calc R 1
C C19 0.3693(5) 0.7909(3) 1.1617(3) 0.0883(12) Uani d U 1
H H37 0.4468 0.7665 1.1849 0.106 Uiso calc R 1
C C20 0.3776(4) 0.8483(2) 1.09632(19) 0.0579(8) Uani d U 1
C C21 0.5052(3) 0.8664(2) 1.05811(19) 0.0524(7) Uani d U 1
C C22 0.6242(4) 0.8126(3) 1.0751(2) 0.0701(10) Uani d U 1
H H33 0.6271 0.7624 1.1131 0.084 Uiso calc R 1
C C23 0.7371(4) 0.8343(3) 1.0354(3) 0.0775(11) Uani d U 1
H H23 0.8169 0.7986 1.0468 0.093 Uiso calc R 1
C C24 0.7348(3) 0.9067(3) 0.9799(3) 0.0719(10) Uani d U 1
H H24 0.8118 0.9222 0.9532 0.086 Uiso calc R 1
C C25 0.6136(3) 0.9570(3) 0.9642(2) 0.0634(9) Uani d U 1
H H32 0.6097 1.0066 0.9259 0.076 Uiso calc R 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'
Cu Cu 0.3201 1.2651 '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_publ_flag
O4 Cu1 N1 92.62(8) y
O4 Cu1 N3 91.77(9) y
N1 Cu1 N3 174.65(9) y
O4 Cu1 O1 147.49(9) y
N1 Cu1 O1 82.08(8) y
N3 Cu1 O1 92.57(9) y
O4 Cu1 N2 109.51(10) y
N1 Cu1 N2 104.07(9) y
N3 Cu1 N2 77.29(10) y
O1 Cu1 N2 102.88(9) y
C5 N1 C2 119.8(2) ?
C5 N1 Cu1 126.40(17) ?
C2 N1 Cu1 113.27(15) ?
C16 N2 C20 119.4(3) ?
C16 N2 Cu1 129.6(2) ?
C20 N2 Cu1 110.3(2) ?
C21 N3 C25 119.3(3) ?
C21 N3 Cu1 119.1(2) ?
C25 N3 Cu1 121.6(2) ?
C7 O4 Cu1 127.02(18) ?
C1 O1 Cu1 114.08(16) ?
C3 O3 H3 109.5 ?
O2 C1 O1 124.4(2) ?
O2 C1 C2 119.6(2) ?
O1 C1 C2 116.1(2) ?
N1 C2 C1 106.54(19) ?
N1 C2 C3 111.06(19) ?
C1 C2 C3 108.7(2) ?
N1 C2 H28 110.1 ?
C1 C2 H28 110.1 ?
C3 C2 H28 110.1 ?
O3 C3 C4 111.7(2) ?
O3 C3 C2 110.6(2) ?
C4 C3 C2 112.0(2) ?
O3 C3 H29 107.4 ?
C4 C3 H29 107.4 ?
C2 C3 H29 107.4 ?
C3 C4 H21A 109.5 ?
C3 C4 H21B 109.5 ?
H21A C4 H21B 109.5 ?
C3 C4 H21C 109.5 ?
H21A C4 H21C 109.5 ?
H21B C4 H21C 109.5 ?
N1 C5 C6 126.0(2) ?
N1 C5 H11 117.0 ?
C6 C5 H11 117.0 ?
C7 C6 C5 121.3(2) ?
C7 C6 C11 120.2(2) ?
C5 C6 C11 118.3(2) ?
O4 C7 C6 125.5(2) ?
O4 C7 C8 116.7(3) ?
C6 C7 C8 117.8(3) ?
C9 C8 C7 122.4(3) ?
C9 C8 H18 118.8 ?
C7 C8 H18 118.8 ?
C8 C9 C10 121.6(3) ?
C8 C9 H19 119.2 ?
C10 C9 H19 119.2 ?
C15 C10 C9 121.3(3) ?
C15 C10 C11 119.8(3) ?
C9 C10 C11 118.9(3) ?
C12 C11 C10 117.3(3) ?
C12 C11 C6 123.7(2) ?
C10 C11 C6 118.9(3) ?
C13 C12 C11 121.5(3) ?
C13 C12 H27 119.3 ?
C11 C12 H27 119.3 ?
C12 C13 C14 121.0(3) ?
C12 C13 H26 119.5 ?
C14 C13 H26 119.5 ?
C15 C14 C13 119.4(3) ?
C15 C14 H25 120.3 ?
C13 C14 H25 120.3 ?
C14 C15 C10 120.9(3) ?
C14 C15 H15 119.5 ?
C10 C15 H15 119.5 ?
N2 C16 C17 121.3(4) ?
N2 C16 H17 119.3 ?
C17 C16 H17 119.3 ?
C18 C17 C16 119.4(5) ?
C18 C17 H22 120.3 ?
C16 C17 H22 120.3 ?
C19 C18 C17 119.5(4) ?
C19 C18 H36 120.3 ?
C17 C18 H36 120.3 ?
C18 C19 C20 119.1(4) ?
C18 C19 H37 120.4 ?
C20 C19 H37 120.4 ?
N2 C20 C19 121.1(4) ?
N2 C20 C21 116.2(3) ?
C19 C20 C21 122.7(4) ?
N3 C21 C22 120.3(4) ?
N3 C21 C20 115.7(3) ?
C22 C21 C20 123.9(3) ?
C23 C22 C21 119.3(4) ?
C23 C22 H33 120.4 ?
C21 C22 H33 120.4 ?
C24 C23 C22 121.2(3) ?
C24 C23 H23 119.4 ?
C22 C23 H23 119.4 ?
C23 C24 C25 117.5(4) ?
C23 C24 H24 121.3 ?
C25 C24 H24 121.3 ?
N3 C25 C24 122.4(4) ?
N3 C25 H32 118.8 ?
C24 C25 H32 118.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O4 1.925(2) y
Cu1 N1 1.926(2) y
Cu1 N3 2.005(2) y
Cu1 O1 2.0236(18) y
Cu1 N2 2.231(3) y
N1 C5 1.292(3) ?
N1 C2 1.457(3) ?
N2 C16 1.338(4) ?
N2 C20 1.345(4) ?
N3 C21 1.337(4) ?
N3 C25 1.352(4) ?
O4 C7 1.295(4) ?
O2 C1 1.240(3) ?
O1 C1 1.269(3) ?
O3 C3 1.415(3) ?
O3 H3 0.8200 ?
C1 C2 1.533(4) ?
C2 C3 1.548(4) ?
C2 H28 0.9800 ?
C3 C4 1.522(4) ?
C3 H29 0.9800 ?
C4 H21A 0.9600 ?
C4 H21B 0.9600 ?
C4 H21C 0.9600 ?
C5 C6 1.428(3) ?
C5 H11 0.9300 ?
C6 C7 1.417(4) ?
C6 C11 1.452(3) ?
C7 C8 1.425(4) ?
C8 C9 1.346(5) ?
C8 H18 0.9300 ?
C9 C10 1.417(5) ?
C9 H19 0.9300 ?
C10 C15 1.415(4) ?
C10 C11 1.422(4) ?
C11 C12 1.400(4) ?
C12 C13 1.376(4) ?
C12 H27 0.9300 ?
C13 C14 1.390(5) ?
C13 H26 0.9300 ?
C14 C15 1.363(5) ?
C14 H25 0.9300 ?
C15 H15 0.9300 ?
C16 C17 1.384(5) ?
C16 H17 0.9300 ?
C17 C18 1.376(7) ?
C17 H22 0.9300 ?
C18 C19 1.362(7) ?
C18 H36 0.9300 ?
C19 C20 1.397(5) ?
C19 H37 0.9300 ?
C20 C21 1.469(5) ?
C21 C22 1.390(5) ?
C22 C23 1.366(6) ?
C22 H33 0.9300 ?
C23 C24 1.352(6) ?
C23 H23 0.9300 ?
C24 C25 1.384(5) ?
C24 H24 0.9300 ?
C25 H32 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
_geom_hbond_publ_flag
O3 H3 O2 4_477 0.82 1.99 2.808(3) 178 y
C5 H11 O2 4_477 0.93 2.49 3.311(3) 147 y
C12 H27 O2 4_477 0.93 2.50 3.431(4) 174 y
C14 H25 O3 2_474 0.93 2.52 3.445(4) 177 y
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
C1 C2 C3 C4 71.0(3)
