#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/28/2212841.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_2212841
loop_
_publ_author_name
'Li Wang'
'Jian-Fang Dong'
'Lian-Zhi Li'
'Lin-Wei Li'
'Da-Qi Wang'
_publ_section_title
Bis[1-(1-naphthyliminomethyl)-2-naphtholato-κ²N,O]copper(II)
_journal_coeditor_code           CV2211
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1059
_journal_page_last               m1060
_journal_paper_doi               10.1107/S160053680701152X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C21 H14 N1 O1)2]'
_chemical_formula_moiety         'C42 H28 Cu N2 O2'
_chemical_formula_sum            'C42 H28 Cu N2 O2'
_chemical_formula_weight         656.20
_chemical_name_systematic
;
Bis[1-(1-naphthyliminomethyl)2-naphtholato-κ²N,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                 109.405(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.958(4)
_cell_length_b                   14.5062(17)
_cell_length_c                   12.515(9)
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.8035
_cell_measurement_theta_min      2.230
_cell_volume                     1533.9(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Siemens SMART 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  0.0701
_diffrn_reflns_av_sigmaI/netI    0.1075
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9233
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.9149
_exptl_absorpt_correction_T_min  0.8223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.535
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1545
_refine_ls_R_factor_gt           0.0609
_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)+(0.1038P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.2123
_reflns_number_gt                1635
_reflns_number_total             3581
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2211.cif
_cod_data_source_block           I
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1534.0(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2212841
_cod_database_fobs_code          2212841
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
Cu Cu1 0.0000 0.5000 1.0000 0.0475(3) Uani d S 1
N N1 0.1476(5) 0.3945(3) 1.0218(3) 0.0510(10) Uani d . 1
O O1 -0.0347(4) 0.4994(2) 0.8441(3) 0.0551(9) Uani d . 1
C C1 0.1721(6) 0.3471(3) 0.9409(4) 0.0517(13) Uani d . 1
H H1 0.2410 0.2974 0.9628 0.062 Uiso calc R 1
C C2 0.1040(5) 0.3636(3) 0.8219(3) 0.0403(10) Uani d . 1
C C3 0.0045(5) 0.4394(3) 0.7813(4) 0.0457(11) Uani d . 1
C C4 -0.0578(6) 0.4551(4) 0.6610(4) 0.0536(13) Uani d . 1
H H4 -0.1221 0.5060 0.6333 0.064 Uiso calc R 1
C C5 -0.0245(6) 0.3974(4) 0.5884(4) 0.0554(13) Uani d . 1
H H5 -0.0689 0.4086 0.5111 0.067 Uiso calc R 1
C C6 0.0759(6) 0.3202(3) 0.6253(4) 0.0478(12) Uani d . 1
C C7 0.1392(6) 0.3010(3) 0.7431(4) 0.0457(11) Uani d . 1
C C8 0.2369(6) 0.2230(4) 0.7754(4) 0.0580(14) Uani d . 1
H H8 0.2793 0.2083 0.8519 0.070 Uiso calc R 1
C C9 0.2715(8) 0.1682(4) 0.6984(5) 0.0734(17) Uani d . 1
H H9 0.3357 0.1168 0.7233 0.088 Uiso calc R 1
C C10 0.2125(8) 0.1880(4) 0.5830(5) 0.0730(17) Uani d . 1
H H10 0.2396 0.1518 0.5308 0.088 Uiso calc R 1
C C11 0.1139(7) 0.2617(4) 0.5487(4) 0.0649(16) Uani d . 1
H H11 0.0701 0.2738 0.4716 0.078 Uiso calc R 1
C C12 0.2285(6) 0.3617(3) 1.1354(4) 0.0487(12) Uani d . 1
C C13 0.1791(7) 0.2869(4) 1.1766(4) 0.0601(14) Uani d . 1
H H13 0.0985 0.2514 1.1278 0.072 Uiso calc R 1
C C14 0.2435(7) 0.2597(4) 1.2902(4) 0.0639(15) Uani d . 1
H H14 0.2064 0.2070 1.3156 0.077 Uiso calc R 1
C C15 0.3607(7) 0.3109(5) 1.3628(4) 0.0710(17) Uani d . 1
H H15 0.4013 0.2947 1.4389 0.085 Uiso calc R 1
C C16 0.4219(6) 0.3903(4) 1.3219(4) 0.0558(13) Uani d . 1
C C17 0.3519(5) 0.4133(3) 1.2059(4) 0.0491(12) Uani d . 1
C C18 0.4170(7) 0.4927(4) 1.1643(6) 0.0712(16) Uani d . 1
H H18 0.3782 0.5093 1.0882 0.085 Uiso calc R 1
C C19 0.5368(8) 0.5422(5) 1.2399(7) 0.088(2) Uani d . 1
H H19 0.5767 0.5939 1.2148 0.106 Uiso calc R 1
C C20 0.5993(9) 0.5168(6) 1.3527(8) 0.105(3) Uani d . 1
H H20 0.6828 0.5504 1.4014 0.126 Uiso calc R 1
C C21 0.5412(7) 0.4447(6) 1.3925(6) 0.090(2) Uani d . 1
H H21 0.5817 0.4308 1.4693 0.108 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'
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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 3_567 . 180.0000(10) ?
O1 Cu1 N1 3_567 3_567 90.69(14) ?
O1 Cu1 N1 . . 90.69(14) y
O1 Cu1 N1 . 3_567 89.31(14) y
O1 Cu1 N1 3_567 . 89.31(14) ?
N1 Cu1 N1 3_567 . 180.000(2) ?
C1 N1 C12 . . 115.6(4) ?
C1 N1 Cu1 . . 125.3(3) ?
C12 N1 Cu1 . . 118.9(3) ?
C3 O1 Cu1 . . 130.6(3) ?
N1 C1 C2 . . 126.8(4) ?
N1 C1 H1 . . 116.6 ?
C2 C1 H1 . . 116.6 ?
C3 C2 C1 . . 120.6(4) ?
C3 C2 C7 . . 120.1(4) ?
C1 C2 C7 . . 119.3(4) ?
O1 C3 C2 . . 125.1(4) ?
O1 C3 C4 . . 116.0(4) ?
C2 C3 C4 . . 118.9(4) ?
C5 C4 C3 . . 121.0(5) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 122.3(4) ?
C4 C5 H5 . . 118.9 ?
C6 C5 H5 . . 118.9 ?
C11 C6 C5 . . 121.9(4) ?
C11 C6 C7 . . 119.1(5) ?
C5 C6 C7 . . 119.0(4) ?
C8 C7 C6 . . 116.9(4) ?
C8 C7 C2 . . 124.3(4) ?
C6 C7 C2 . . 118.7(4) ?
C9 C8 C7 . . 122.2(5) ?
C9 C8 H8 . . 118.9 ?
C7 C8 H8 . . 118.9 ?
C8 C9 C10 . . 121.1(5) ?
C8 C9 H9 . . 119.4 ?
C10 C9 H9 . . 119.4 ?
C11 C10 C9 . . 118.1(5) ?
C11 C10 H10 . . 121.0 ?
C9 C10 H10 . . 121.0 ?
C10 C11 C6 . . 122.6(5) ?
C10 C11 H11 . . 118.7 ?
C6 C11 H11 . . 118.7 ?
C13 C12 C17 . . 119.3(5) ?
C13 C12 N1 . . 121.6(5) ?
C17 C12 N1 . . 118.9(4) ?
C12 C13 C14 . . 122.8(5) ?
C12 C13 H13 . . 118.6 ?
C14 C13 H13 . . 118.6 ?
C15 C14 C13 . . 119.4(5) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.0(5) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C21 C16 C17 . . 120.3(6) ?
C21 C16 C15 . . 122.2(6) ?
C17 C16 C15 . . 117.5(5) ?
C12 C17 C16 . . 120.9(5) ?
C12 C17 C18 . . 121.9(5) ?
C16 C17 C18 . . 117.2(5) ?
C19 C18 C17 . . 118.6(6) ?
C19 C18 H18 . . 120.7 ?
C17 C18 H18 . . 120.7 ?
C18 C19 C20 . . 121.5(7) ?
C18 C19 H19 . . 119.3 ?
C20 C19 H19 . . 119.3 ?
C21 C20 C19 . . 120.8(7) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 C16 . . 121.5(7) ?
C20 C21 H21 . . 119.2 ?
C16 C21 H21 . . 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 3_567 1.871(3) ?
Cu1 O1 . 1.871(3) y
Cu1 N1 3_567 1.981(4) ?
Cu1 N1 . 1.981(4) y
N1 C1 . 1.301(6) ?
N1 C12 . 1.445(6) ?
O1 C3 . 1.297(5) ?
C1 C2 . 1.430(6) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.400(6) ?
C2 C7 . 1.451(6) ?
C3 C4 . 1.439(6) ?
C4 C5 . 1.339(7) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.415(7) ?
C5 H5 . 0.9300 ?
C6 C11 . 1.404(6) ?
C6 C7 . 1.420(6) ?
C7 C8 . 1.405(7) ?
C8 C9 . 1.362(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.393(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.363(7) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.339(7) ?
C12 C17 . 1.382(6) ?
C13 C14 . 1.401(7) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.358(7) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.441(8) ?
C15 H15 . 0.9300 ?
C16 C21 . 1.385(8) ?
C16 C17 . 1.417(6) ?
C17 C18 . 1.463(7) ?
C18 C19 . 1.374(8) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.385(10) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.336(10) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
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
O1 Cu1 N1 C1 3_567 172.2(4)
O1 Cu1 N1 C1 . -7.8(4)
N1 Cu1 N1 C1 3_567 -4E1(10)
O1 Cu1 N1 C12 3_567 -3.3(4)
O1 Cu1 N1 C12 . 176.7(4)
N1 Cu1 N1 C12 3_567 15E1(10)
O1 Cu1 O1 C3 3_567 0E1(10)
N1 Cu1 O1 C3 3_567 -169.0(4)
N1 Cu1 O1 C3 . 11.0(4)
C12 N1 C1 C2 . 178.6(4)
Cu1 N1 C1 C2 . 2.9(8)
N1 C1 C2 C3 . 2.9(8)
N1 C1 C2 C7 . -177.2(5)
Cu1 O1 C3 C2 . -8.9(7)
Cu1 O1 C3 C4 . 172.7(3)
C1 C2 C3 O1 . -0.2(7)
C7 C2 C3 O1 . 179.9(4)
C1 C2 C3 C4 . 178.2(4)
C7 C2 C3 C4 . -1.8(7)
O1 C3 C4 C5 . 179.9(5)
C2 C3 C4 C5 . 1.4(8)
C3 C4 C5 C6 . -1.7(8)
C4 C5 C6 C11 . -178.1(5)
C4 C5 C6 C7 . 2.4(8)
C11 C6 C7 C8 . -0.2(7)
C5 C6 C7 C8 . 179.3(5)
C11 C6 C7 C2 . 177.8(5)
C5 C6 C7 C2 . -2.7(7)
C3 C2 C7 C8 . -179.7(5)
C1 C2 C7 C8 . 0.3(7)
C3 C2 C7 C6 . 2.4(7)
C1 C2 C7 C6 . -177.5(4)
C6 C7 C8 C9 . 0.6(8)
C2 C7 C8 C9 . -177.3(5)
C7 C8 C9 C10 . 0.8(9)
C8 C9 C10 C11 . -2.5(9)
C9 C10 C11 C6 . 2.9(9)
C5 C6 C11 C10 . 178.9(5)
C7 C6 C11 C10 . -1.5(8)
C1 N1 C12 C13 . -75.5(6)
Cu1 N1 C12 C13 . 100.5(5)
C1 N1 C12 C17 . 109.8(5)
Cu1 N1 C12 C17 . -74.3(5)
C17 C12 C13 C14 . 2.3(8)
N1 C12 C13 C14 . -172.4(5)
C12 C13 C14 C15 . 0.3(9)
C13 C14 C15 C16 . -2.5(8)
C14 C15 C16 C21 . 180.0(5)
C14 C15 C16 C17 . 2.0(8)
C13 C12 C17 C16 . -2.7(7)
N1 C12 C17 C16 . 172.1(4)
C13 C12 C17 C18 . 176.5(5)
N1 C12 C17 C18 . -8.7(7)
C21 C16 C17 C12 . -177.4(5)
C15 C16 C17 C12 . 0.6(7)
C21 C16 C17 C18 . 3.4(7)
C15 C16 C17 C18 . -178.6(5)
C12 C17 C18 C19 . 178.2(5)
C16 C17 C18 C19 . -2.6(8)
C17 C18 C19 C20 . 2.0(10)
C18 C19 C20 C21 . -2.2(12)
C19 C20 C21 C16 . 3.0(12)
C17 C16 C21 C20 . -3.7(10)
C15 C16 C21 C20 . 178.4(7)
