#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/80/2238066.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_2238066
loop_
_publ_author_name
'Benslimane, Meriem'
'Redjel, Yasmine Kheira'
'Merazig, Hocine'
'Daran, Jean-Claude'
_publ_section_title
;
 Bis(cinnamato-κO)(1,10-phenanthroline-κ²N,N')copper(II)
;
_journal_coeditor_code           VM2193
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m277
_journal_paper_doi               10.1107/S1600536813010350
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '[Cu (C9 H7 O2)2 (C12 H8 N2)]'
_chemical_formula_moiety         'C30 H22 Cu N2 O4'
_chemical_formula_sum            'C30 H22 Cu N2 O4'
_chemical_formula_weight         538.04
_chemical_name_systematic
;
Bis(cinnamato-κO)(1,10-phenanthroline-κ²N,N')copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.0
_cell_angle_beta                 109.623(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   24.486(5)
_cell_length_b                   9.986(5)
_cell_length_c                   10.710(5)
_cell_measurement_reflns_used    1791
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.91
_cell_measurement_theta_min      2.80
_cell_volume                     2466.7(18)
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6897
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         3.20
_exptl_absorpt_coefficient_mu    0.926
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.374
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0392
_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)+(0.0509P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                1698
_reflns_number_total             2172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            vm2193.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2238066
_cod_database_fobs_code          2238066
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -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_symmetry_multiplicity
Cu Cu1 0.0000 0.45859(4) 0.2500 0.03280(19) Uani d S 1 2
O O1 0.04096(9) 0.59098(18) 0.3818(2) 0.0401(5) Uani d . 1 1
O O2 0.10280(9) 0.5414(2) 0.2789(2) 0.0519(6) Uani d . 1 1
N N1 -0.03295(11) 0.3059(2) 0.1237(2) 0.0347(6) Uani d . 1 1
C C1 0.09029(13) 0.6012(3) 0.3663(3) 0.0370(7) Uani d . 1 1
C C4 0.17627(13) 0.7909(3) 0.6862(3) 0.0395(7) Uani d . 1 1
C C3 0.13359(13) 0.7143(3) 0.5815(3) 0.0408(7) Uani d . 1 1
H H3 0.1023 0.6808 0.6023 0.049 Uiso calc R 1 1
C C10 -0.01823(13) 0.1841(2) 0.1824(3) 0.0356(7) Uani d . 1 1
C C2 0.13404(13) 0.6868(3) 0.4616(3) 0.0404(7) Uani d . 1 1
H H2 0.1635 0.7232 0.4355 0.049 Uiso calc R 1 1
C C11 -0.03787(14) 0.0630(3) 0.1159(3) 0.0441(8) Uani d . 1 1
C C15 -0.01798(15) -0.0590(3) 0.1870(4) 0.0557(10) Uani d . 1 1
H H15 -0.0303 -0.1404 0.1446 0.067 Uiso calc R 1 1
C C13 -0.08989(16) 0.1950(3) -0.0730(3) 0.0532(9) Uani d . 1 1
H H13 -0.1148 0.2016 -0.1601 0.064 Uiso calc R 1 1
C C14 -0.06717(14) 0.3102(3) -0.0004(3) 0.0452(8) Uani d . 1 1
H H14 -0.0766 0.3932 -0.0415 0.054 Uiso calc R 1 1
C C12 -0.07512(16) 0.0728(3) -0.0149(4) 0.0553(9) Uani d . 1 1
H H12 -0.0900 -0.0045 -0.0627 0.066 Uiso calc R 1 1
C C5 0.22409(15) 0.8532(3) 0.6695(4) 0.0561(9) Uani d . 1 1
H H5 0.2299 0.8461 0.5882 0.067 Uiso calc R 1 1
C C9 0.16966(16) 0.8046(4) 0.8080(4) 0.0679(11) Uani d . 1 1
H H9 0.1381 0.7643 0.8227 0.081 Uiso calc R 1 1
C C6 0.26283(16) 0.9246(4) 0.7689(4) 0.0698(11) Uani d . 1 1
H H6 0.2946 0.9649 0.7553 0.084 Uiso calc R 1 1
C C7 0.25464(18) 0.9363(4) 0.8886(4) 0.0843(14) Uani d . 1 1
H H7 0.2807 0.9854 0.9566 0.101 Uiso calc R 1 1
C C8 0.20818(19) 0.8758(5) 0.9079(4) 0.0931(16) Uani d . 1 1
H H8 0.2027 0.8831 0.9895 0.112 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 0.0033 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
N1 Cu1 N1 . 2 81.84(14)
C1 O1 Cu1 . . 103.84(18)
C14 N1 C10 . . 118.5(2)
C14 N1 Cu1 . . 129.00(19)
C10 N1 Cu1 . . 112.4(2)
O2 C1 O1 . . 123.2(3)
O2 C1 C2 . . 119.8(3)
O1 C1 C2 . . 117.0(3)
C9 C4 C5 . . 116.8(3)
C9 C4 C3 . . 119.8(3)
C5 C4 C3 . . 123.4(3)
C2 C3 C4 . . 128.1(3)
C2 C3 H3 . . 115.9
C4 C3 H3 . . 115.9
N1 C10 C11 . . 122.9(3)
N1 C10 C10 . 2 116.64(16)
C11 C10 C10 . 2 120.45(19)
C3 C2 C1 . . 123.5(3)
C3 C2 H2 . . 118.2
C1 C2 H2 . . 118.2
C12 C11 C10 . . 116.5(3)
C12 C11 C15 . . 125.7(3)
C10 C11 C15 . . 117.8(3)
C15 C15 C11 2 . 121.72(19)
C15 C15 H15 2 . 119.1
C11 C15 H15 . . 119.1
C12 C13 C14 . . 119.3(3)
C12 C13 H13 . . 120.4
C14 C13 H13 . . 120.4
N1 C14 C13 . . 122.4(3)
N1 C14 H14 . . 118.8
C13 C14 H14 . . 118.8
C13 C12 C11 . . 120.3(3)
C13 C12 H12 . . 119.8
C11 C12 H12 . . 119.8
C6 C5 C4 . . 121.9(3)
C6 C5 H5 . . 119.1
C4 C5 H5 . . 119.1
C8 C9 C4 . . 121.7(3)
C8 C9 H9 . . 119.1
C4 C9 H9 . . 119.1
C5 C6 C7 . . 119.6(3)
C5 C6 H6 . . 120.2
C7 C6 H6 . . 120.2
C8 C7 C6 . . 119.8(4)
C8 C7 H7 . . 120.1
C6 C7 H7 . . 120.1
C9 C8 C7 . . 120.3(4)
C9 C8 H8 . . 119.9
C7 C8 H8 . . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O1 . 1.948(2)
Cu1 O1 2 1.948(2)
Cu1 N1 . 2.018(2)
Cu1 N1 2 2.018(2)
O1 C1 . 1.277(3)
O2 C1 . 1.232(3)
N1 C14 . 1.313(4)
N1 C10 . 1.360(3)
C1 C2 . 1.479(4)
C4 C9 . 1.374(5)
C4 C5 . 1.390(4)
C4 C3 . 1.466(4)
C3 C2 . 1.316(4)
C3 H3 . 0.9300
C10 C11 . 1.404(4)
C10 C10 2 1.424(6)
C2 H2 . 0.9300
C11 C12 . 1.395(5)
C11 C15 . 1.433(4)
C15 C15 2 1.342(7)
C15 H15 . 0.9300
C13 C12 . 1.363(5)
C13 C14 . 1.395(4)
C13 H13 . 0.9300
C14 H14 . 0.9300
C12 H12 . 0.9300
C5 C6 . 1.365(5)
C5 H5 . 0.9300
C9 C8 . 1.365(5)
C9 H9 . 0.9300
C6 C7 . 1.368(5)
C6 H6 . 0.9300
C7 C8 . 1.364(5)
C7 H7 . 0.9300
C8 H8 . 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
C14 H14 O2 5_565 0.9300 2.4900 3.176(5) 131.00 yes
