#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223260.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_2223260
loop_
_publ_author_name
'Wang, B. S.'
'Zhong, H.'
_publ_section_title
Dichlorido(2,9-dimethyl-1,10-phenanthroline-κ²N,N')copper(II)
_journal_coeditor_code           AT2860
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1156
_journal_paper_doi               10.1107/S1600536809034187
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu Cl2 (C14 H12 N2)]'
_chemical_formula_moiety         'C14 H12 Cl2 Cu N2'
_chemical_formula_sum            'C14 H12 Cl2 Cu N2'
_chemical_formula_weight         342.70
_chemical_name_systematic
Dichlorido(2,9-dimethyl-1,10-phenanthroline-κ²N,N')copper(II)
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                   11.239(2)
_cell_length_b                   7.4651(18)
_cell_length_c                   17.663(5)
_cell_measurement_reflns_used    5426
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.978
_cell_measurement_theta_min      2.306
_cell_volume                     1481.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'APEX2 (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10738
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.820
_exptl_absorpt_correction_T_max  0.7011
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plane
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0264
_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)+(0.0553P)²+0.1694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                1601
_reflns_number_total             1951
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2860.cif
_cod_data_source_block           global
_cod_database_code               2223260
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.76127(2) 0.7500 0.610028(14) 0.04178(12) Uani d S 1 . .
N N1 0.79467(16) 0.7500 0.49476(10) 0.0418(4) Uani d S 1 . .
N N2 0.58758(17) 0.7500 0.57229(11) 0.0445(4) Uani d S 1 . .
C C1 1.0098(2) 0.7500 0.50503(18) 0.0684(8) Uani d S 1 . .
H H1A 1.0316 0.8711 0.5170 0.103 Uiso calc PR 0.50 . .
H H1B 1.0728 0.6946 0.4767 0.103 Uiso calc PR 0.50 . .
H H1C 0.9967 0.6843 0.5510 0.103 Uiso calc PR 0.50 . .
C C13 0.6920(2) 0.7500 0.45450(12) 0.0406(5) Uani d S 1 . .
C C11 0.4872(3) 0.7500 0.61234(14) 0.0558(6) Uani d S 1 . .
C C2 0.8982(2) 0.7500 0.45874(15) 0.0517(6) Uani d S 1 . .
C C12 0.58155(19) 0.7500 0.49535(12) 0.0403(5) Uani d S 1 . .
C C14 0.4987(3) 0.7500 0.69623(17) 0.0803(10) Uani d S 1 . .
H H14A 0.5697 0.8130 0.7105 0.120 Uiso calc PR 0.50 . .
H H14B 0.5030 0.6288 0.7142 0.120 Uiso calc PR 0.50 . .
H H14C 0.4307 0.8082 0.7182 0.120 Uiso calc PR 0.50 . .
C C10 0.3763(2) 0.7500 0.5751(2) 0.0711(8) Uani d S 1 . .
H H10 0.3067 0.7500 0.6035 0.085 Uiso calc SR 1 . .
C C8 0.4741(2) 0.7500 0.45551(15) 0.0500(6) Uani d S 1 . .
C C7 0.4757(3) 0.7500 0.37518(16) 0.0624(7) Uani d S 1 . .
H H7 0.4041 0.7500 0.3487 0.075 Uiso calc SR 1 . .
C C5 0.6901(2) 0.7500 0.37527(13) 0.0502(6) Uani d S 1 . .
C C6 0.5787(3) 0.7500 0.33689(15) 0.0610(7) Uani d S 1 . .
H H6 0.5774 0.7500 0.2842 0.073 Uiso calc SR 1 . .
C C9 0.3695(2) 0.7500 0.49900(19) 0.0664(8) Uani d S 1 . .
H H9 0.2957 0.7500 0.4753 0.080 Uiso calc SR 1 . .
C C3 0.9025(3) 0.7500 0.37937(16) 0.0676(8) Uani d S 1 . .
H H3 0.9756 0.7500 0.3547 0.081 Uiso calc SR 1 . .
C C4 0.8005(3) 0.7500 0.33845(16) 0.0687(8) Uani d S 1 . .
H H4 0.8038 0.7500 0.2858 0.082 Uiso calc SR 1 . .
Cl Cl1 0.81305(5) 1.00503(6) 0.66249(3) 0.06566(17) Uani 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'
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'
Cl Cl 0.1484 0.1585 '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
Cl1 Cu1 Cl1 . 7_575 120.23(3) no
N1 Cu1 Cl1 . . 111.53(3) no
N1 Cu1 Cl1 . 7_575 111.53(3) no
N2 Cu1 N1 . . 81.60(7) no
N2 Cu1 Cl1 . . 112.78(2) no
N2 Cu1 Cl1 . 7_575 112.78(2) no
C2 N1 C13 . . 119.7(2) ?
C2 N1 Cu1 . . 129.12(17) ?
C13 N1 Cu1 . . 111.21(15) ?
C11 N2 C12 . . 119.2(2) ?
C11 N2 Cu1 . . 129.05(18) ?
C12 N2 Cu1 . . 111.71(14) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C13 C5 . . 122.6(2) ?
N1 C13 C12 . . 118.2(2) ?
C5 C13 C12 . . 119.2(2) ?
N2 C11 C10 . . 120.1(2) ?
N2 C11 C14 . . 117.1(3) ?
C10 C11 C14 . . 122.8(3) ?
N1 C2 C3 . . 120.6(2) ?
N1 C2 C1 . . 118.2(2) ?
C3 C2 C1 . . 121.1(2) ?
N2 C12 C8 . . 123.1(2) ?
N2 C12 C13 . . 117.30(19) ?
C8 C12 C13 . . 119.6(2) ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C9 C10 C11 . . 121.1(3) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C12 C8 C9 . . 116.6(2) ?
C12 C8 C7 . . 119.5(2) ?
C9 C8 C7 . . 123.9(2) ?
C6 C7 C8 . . 121.0(2) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C13 C5 C4 . . 116.7(2) ?
C13 C5 C6 . . 119.4(2) ?
C4 C5 C6 . . 123.9(2) ?
C7 C6 C5 . . 121.3(2) ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C10 C9 C8 . . 119.9(3) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C4 C3 C2 . . 120.3(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
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 Cl1 . 2.1958(6) no
Cu1 Cl1 7_575 2.1958(6) no
Cu1 N1 . 2.070(2) no
Cu1 N2 . 2.063(2) no
N1 C2 . 1.326(3) ?
N1 C13 . 1.355(3) ?
N2 C11 . 1.331(3) ?
N2 C12 . 1.361(3) ?
C1 C2 . 1.498(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C13 C5 . 1.400(3) ?
C13 C12 . 1.436(3) ?
C11 C10 . 1.409(4) ?
C11 C14 . 1.487(4) ?
C2 C3 . 1.403(3) ?
C12 C8 . 1.398(3) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C10 C9 . 1.346(5) ?
C10 H10 . 0.9300 ?
C8 C9 . 1.404(4) ?
C8 C7 . 1.419(4) ?
C7 C6 . 1.341(4) ?
C7 H7 . 0.9300 ?
C5 C4 . 1.401(4) ?
C5 C6 . 1.423(4) ?
C6 H6 . 0.9300 ?
C9 H9 . 0.9300 ?
C3 C4 . 1.355(4) ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9300 ?
