#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019477.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_2019477
loop_
_publ_author_name
'Krause, Jeanette A.'
'Zhao, Daoli'
'Chatterjee, Sayandev'
'Falcon, Roland'
'Stoltz, Kristen'
'Warren, John C.'
'Wiswell, Sara E.'
'Connick, William B.'
'Collins, Sibrina N.'
_publ_section_title
;
 In-house and synchrotron X-ray diffraction studies of
 2-phenyl-1,10-phenanthroline, protonated salts, complexes with gold(III)
 and copper(II), and an orthometallation product with palladium(II)
;
_journal_coeditor_code           GZ3246
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              260
_journal_page_last               266
_journal_paper_doi               10.1107/S2053229614001843
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '[Cu Cl2 (C18 H12 N2)]'
_chemical_formula_moiety         'C18 H12 Cl2 Cu N2'
_chemical_formula_sum            'C18 H12 Cl2 Cu N2'
_chemical_formula_weight         390.74
_chemical_name_systematic
;
Dichlorido(2-phenyl-1,10-phenanthroline-κ²N,N')copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 103.4080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9946(2)
_cell_length_b                   19.2773(5)
_cell_length_c                   10.3823(2)
_cell_measurement_reflns_used    7410
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.59
_cell_measurement_theta_min      4.38
_cell_volume                     1556.45(6)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008b)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART6000 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13203
_diffrn_reflns_theta_full        68.03
_diffrn_reflns_theta_max         68.03
_diffrn_reflns_theta_min         4.59
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    5.120
_exptl_absorpt_correction_T_max  0.9506
_exptl_absorpt_correction_T_min  0.4275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blade
_exptl_crystal_F_000             788
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0287
_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)+(0.0440P)²+0.9787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                2444
_reflns_number_total             2755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gz3246sup1.cif
_cod_data_source_block           VII
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2019477
_cod_database_fobs_code          2019477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.26805(4) 0.547963(15) 0.87148(3) 0.02034(12) Uani d . 1 1
Cl Cl1 0.34828(7) 0.53638(3) 1.08968(5) 0.02637(14) Uani d . 1 1
Cl Cl2 0.14664(7) 0.65355(3) 0.85895(5) 0.02490(14) Uani d . 1 1
N N1 0.1660(2) 0.45241(9) 0.82921(18) 0.0194(4) Uani d . 1 1
N N2 0.2993(2) 0.54171(9) 0.68323(17) 0.0182(4) Uani d . 1 1
C C1 0.0952(3) 0.41107(12) 0.9035(2) 0.0244(5) Uani d . 1 1
H H1 0.1016 0.4236 0.9930 0.029 Uiso calc R 1 1
C C2 0.0112(3) 0.34939(12) 0.8546(3) 0.0292(5) Uani d . 1 1
H H2 -0.0394 0.3211 0.9102 0.035 Uiso calc R 1 1
C C3 0.0024(3) 0.33003(12) 0.7260(2) 0.0273(5) Uani d . 1 1
H H3 -0.0516 0.2877 0.6926 0.033 Uiso calc R 1 1
C C4 0.0744(3) 0.37363(11) 0.6438(2) 0.0227(5) Uani d . 1 1
C C5 0.1560(3) 0.43456(11) 0.7007(2) 0.0191(4) Uani d . 1 1
C C6 0.0666(3) 0.35997(12) 0.5069(2) 0.0281(5) Uani d . 1 1
H H6 0.0129 0.3187 0.4676 0.034 Uiso calc R 1 1
C C7 0.1345(3) 0.40485(13) 0.4326(2) 0.0281(5) Uani d . 1 1
H H7 0.1283 0.3944 0.3422 0.034 Uiso calc R 1 1
C C8 0.2156(3) 0.46797(12) 0.4878(2) 0.0226(5) Uani d . 1 1
C C9 0.2276(2) 0.48253(11) 0.6227(2) 0.0191(4) Uani d . 1 1
C C10 0.2806(3) 0.51850(13) 0.4144(2) 0.0257(5) Uani d . 1 1
H H10 0.2744 0.5115 0.3228 0.031 Uiso calc R 1 1
C C11 0.3524(3) 0.57743(12) 0.4754(2) 0.0261(5) Uani d . 1 1
H H11 0.3965 0.6114 0.4258 0.031 Uiso calc R 1 1
C C12 0.3624(3) 0.58885(11) 0.6120(2) 0.0207(4) Uani d . 1 1
C C13 0.4401(3) 0.65285(11) 0.6773(2) 0.0224(5) Uani d . 1 1
C C14 0.3999(3) 0.71634(12) 0.6127(2) 0.0278(5) Uani d . 1 1
H H14 0.3309 0.7174 0.5249 0.033 Uiso calc R 1 1
C C15 0.4601(3) 0.77756(13) 0.6758(3) 0.0333(6) Uani d . 1 1
H H15 0.4296 0.8207 0.6327 0.040 Uiso calc R 1 1
C C16 0.5651(3) 0.77571(13) 0.8022(3) 0.0324(6) Uani d . 1 1
H H16 0.6056 0.8178 0.8460 0.039 Uiso calc R 1 1
C C17 0.6118(3) 0.71253(13) 0.8657(2) 0.0303(5) Uani d . 1 1
H H17 0.6868 0.7116 0.9513 0.036 Uiso calc R 1 1
C C18 0.5491(3) 0.65125(12) 0.8042(2) 0.0261(5) Uani d . 1 1
H H18 0.5796 0.6082 0.8477 0.031 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
N1 Cu1 N2 82.56(7) y
N1 Cu1 Cl1 97.85(5) y
N2 Cu1 Cl1 154.97(5) y
N1 Cu1 Cl2 131.77(5) y
N2 Cu1 Cl2 98.40(5) y
Cl1 Cu1 Cl2 99.74(2) y
C1 N1 C5 118.86(19) ?
C1 N1 Cu1 128.88(15) ?
C5 N1 Cu1 111.83(14) ?
C12 N2 C9 118.98(18) ?
C12 N2 Cu1 129.50(15) ?
C9 N2 Cu1 111.16(14) ?
N1 C1 C2 122.2(2) ?
N1 C1 H1 118.9 ?
C2 C1 H1 118.9 ?
C3 C2 C1 119.7(2) ?
C3 C2 H2 120.1 ?
C1 C2 H2 120.1 ?
C2 C3 C4 119.3(2) ?
C2 C3 H3 120.3 ?
C4 C3 H3 120.3 ?
C5 C4 C3 117.2(2) ?
C5 C4 C6 118.7(2) ?
C3 C4 C6 124.1(2) ?
N1 C5 C4 122.6(2) ?
N1 C5 C9 116.75(19) ?
C4 C5 C9 120.6(2) ?
C7 C6 C4 121.1(2) ?
C7 C6 H6 119.4 ?
C4 C6 H6 119.4 ?
C6 C7 C8 121.2(2) ?
C6 C7 H7 119.4 ?
C8 C7 H7 119.4 ?
C10 C8 C9 116.8(2) ?
C10 C8 C7 124.0(2) ?
C9 C8 C7 119.1(2) ?
N2 C9 C8 123.3(2) ?
N2 C9 C5 117.39(18) ?
C8 C9 C5 119.3(2) ?
C11 C10 C8 119.6(2) ?
C11 C10 H10 120.2 ?
C8 C10 H10 120.2 ?
C10 C11 C12 121.0(2) ?
C10 C11 H11 119.5 ?
C12 C11 H11 119.5 ?
N2 C12 C11 120.3(2) ?
N2 C12 C13 119.09(19) ?
C11 C12 C13 120.6(2) ?
C14 C13 C18 119.6(2) ?
C14 C13 C12 119.2(2) ?
C18 C13 C12 121.18(19) ?
C15 C14 C13 120.4(2) ?
C15 C14 H14 119.8 ?
C13 C14 H14 119.8 ?
C14 C15 C16 119.7(2) ?
C14 C15 H15 120.2 ?
C16 C15 H15 120.2 ?
C15 C16 C17 120.5(2) ?
C15 C16 H16 119.7 ?
C17 C16 H16 119.7 ?
C18 C17 C16 120.0(2) ?
C18 C17 H17 120.0 ?
C16 C17 H17 120.0 ?
C17 C18 C13 119.7(2) ?
C17 C18 H18 120.1 ?
C13 C18 H18 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 2.0212(17) y
Cu1 N2 2.0306(18) y
Cu1 Cl1 2.2180(6) y
Cu1 Cl2 2.2458(6) y
N1 C1 1.324(3) ?
N1 C5 1.362(3) ?
N2 C12 1.341(3) ?
N2 C9 1.363(3) ?
C1 C2 1.402(3) ?
C1 H1 0.9500 ?
C2 C3 1.372(3) ?
C2 H2 0.9500 ?
C3 C4 1.412(3) ?
C3 H3 0.9500 ?
C4 C5 1.406(3) ?
C4 C6 1.433(3) ?
C5 C9 1.433(3) ?
C6 C7 1.354(3) ?
C6 H6 0.9500 ?
C7 C8 1.434(3) ?
C7 H7 0.9500 ?
C8 C10 1.409(3) ?
C8 C9 1.410(3) ?
C10 C11 1.361(3) ?
C10 H10 0.9500 ?
C11 C12 1.420(3) ?
C11 H11 0.9500 ?
C12 C13 1.474(3) ?
C13 C14 1.397(3) ?
C13 C18 1.401(3) ?
C14 C15 1.381(4) ?
C14 H14 0.9500 ?
C15 C16 1.385(4) ?
C15 H15 0.9500 ?
C16 C17 1.394(4) ?
C16 H16 0.9500 ?
C17 C18 1.381(3) ?
C17 H17 0.9500 ?
C18 H18 0.9500 ?
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
N2 Cu1 N1 C1 -177.1(2)
Cl1 Cu1 N1 C1 28.13(19)
Cl2 Cu1 N1 C1 -82.5(2)
N2 Cu1 N1 C5 -4.79(14)
Cl1 Cu1 N1 C5 -159.53(13)
Cl2 Cu1 N1 C5 89.86(14)
N1 Cu1 N2 C12 177.69(18)
Cl1 Cu1 N2 C12 -89.7(2)
Cl2 Cu1 N2 C12 46.41(18)
N1 Cu1 N2 C9 4.74(13)
Cl1 Cu1 N2 C9 97.38(17)
Cl2 Cu1 N2 C9 -126.54(13)
C5 N1 C1 C2 0.3(3)
Cu1 N1 C1 C2 172.20(16)
N1 C1 C2 C3 0.7(3)
C1 C2 C3 C4 -1.7(3)
C2 C3 C4 C5 1.6(3)
C2 C3 C4 C6 -177.4(2)
C1 N1 C5 C4 -0.4(3)
Cu1 N1 C5 C4 -173.61(16)
C1 N1 C5 C9 177.24(18)
Cu1 N1 C5 C9 4.0(2)
C3 C4 C5 N1 -0.5(3)
C6 C4 C5 N1 178.51(19)
C3 C4 C5 C9 -178.09(19)
C6 C4 C5 C9 0.9(3)
C5 C4 C6 C7 -0.7(3)
C3 C4 C6 C7 178.3(2)
C4 C6 C7 C8 -0.4(3)
C6 C7 C8 C10 -176.5(2)
C6 C7 C8 C9 1.3(3)
C12 N2 C9 C8 -0.1(3)
Cu1 N2 C9 C8 173.68(16)
C12 N2 C9 C5 -177.77(18)
Cu1 N2 C9 C5 -4.0(2)
C10 C8 C9 N2 -0.7(3)
C7 C8 C9 N2 -178.67(19)
C10 C8 C9 C5 176.96(18)
C7 C8 C9 C5 -1.0(3)
N1 C5 C9 N2 0.0(3)
C4 C5 C9 N2 177.69(18)
N1 C5 C9 C8 -177.79(18)
C4 C5 C9 C8 -0.1(3)
C9 C8 C10 C11 0.8(3)
C7 C8 C10 C11 178.7(2)
C8 C10 C11 C12 -0.2(3)
C9 N2 C12 C11 0.7(3)
Cu1 N2 C12 C11 -171.73(15)
C9 N2 C12 C13 -179.94(18)
Cu1 N2 C12 C13 7.6(3)
C10 C11 C12 N2 -0.6(3)
C10 C11 C12 C13 -179.9(2)
N2 C12 C13 C14 -135.8(2)
C11 C12 C13 C14 43.5(3)
N2 C12 C13 C18 42.2(3)
C11 C12 C13 C18 -138.5(2)
C18 C13 C14 C15 -3.2(3)
C12 C13 C14 C15 174.9(2)
C13 C14 C15 C16 2.0(4)
C14 C15 C16 C17 0.6(4)
C15 C16 C17 C18 -2.0(4)
C16 C17 C18 C13 0.8(3)
C14 C13 C18 C17 1.8(3)
C12 C13 C18 C17 -176.2(2)
