#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/29/2212967.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_2212967
loop_
_publ_author_name
'Wang, Jia'
'Ye, Jun-Wei'
'Wang, Yue'
_publ_section_title
;
 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
;
_journal_coeditor_code           NC2031
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2007
_journal_page_last               o2008
_journal_paper_doi               10.1107/S1600536807012974
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C26 H20 N2'
_chemical_formula_moiety         'C26 H20 N2'
_chemical_formula_sum            'C26 H20 N2'
_chemical_formula_weight         360.44
_chemical_name_systematic
;
2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline
;
_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                90.00
_cell_angle_beta                 109.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.4953(19)
_cell_length_b                   10.6869(10)
_cell_length_c                   11.4661(10)
_cell_measurement_reflns_used    5602
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      1.88
_cell_volume                     1909.8(5)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8924
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.31
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9783
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.162
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0398
_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)+(0.0315P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                1182
_reflns_number_total             2194
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2031.cif
_cod_data_source_block           I
_cod_original_cell_volume        1909.7(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2212967
_cod_database_fobs_code          2212967
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
C C1 0.39584(10) 0.43765(14) 1.01487(14) 0.0407(4) Uani d . 1
C C2 0.37423(10) 0.54724(14) 0.94448(13) 0.0415(4) Uani d . 1
H H2 0.3441 0.5416 0.8605 0.050 Uiso calc R 1
C C3 0.39665(9) 0.66245(14) 0.99720(13) 0.0369(4) Uani d . 1
C C4 0.44689(9) 0.66567(13) 1.12434(12) 0.0347(3) Uani d . 1
C C5 0.47134(9) 0.55137(13) 1.18605(12) 0.0350(4) Uani d . 1
C C6 0.47574(10) 0.77956(13) 1.18997(11) 0.0408(4) Uani d . 1
H H6 0.4607 0.8555 1.1489 0.049 Uiso calc R 1
C C7 0.36349(12) 0.31287(15) 0.95793(15) 0.0601(5) Uani d . 1
H H7A 0.4040 0.2489 0.9975 0.090 Uiso calc R 1
H H7B 0.3566 0.3149 0.8715 0.090 Uiso calc R 1
H H7C 0.3092 0.2952 0.9684 0.090 Uiso calc R 1
C C8 0.37227(10) 0.77897(13) 0.92277(12) 0.0380(4) Uani d . 1
C C9 0.40088(10) 0.79918(15) 0.82345(13) 0.0480(4) Uani d . 1
H H9 0.4332 0.7383 0.8009 0.058 Uiso calc R 1
C C10 0.38146(12) 0.90951(16) 0.75808(15) 0.0581(5) Uani d . 1
H H10 0.4015 0.9231 0.6921 0.070 Uiso calc R 1
C C11 0.33264(11) 1.00009(17) 0.78940(15) 0.0552(5) Uani d . 1
H H11 0.3212 1.0753 0.7462 0.066 Uiso calc R 1
C C12 0.30098(11) 0.97885(15) 0.88455(15) 0.0523(5) Uani d . 1
H H12 0.2663 1.0383 0.9039 0.063 Uiso calc R 1
C C13 0.32078(10) 0.86947(14) 0.95103(14) 0.0468(4) Uani d . 1
H H13 0.2995 0.8557 1.0157 0.056 Uiso calc R 1
N N1 0.44397(8) 0.43857(10) 1.13279(11) 0.0394(3) 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'
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 C1 C2 . . 122.43(14)
N1 C1 C7 . . 117.29(14)
C2 C1 C7 . . 120.28(14)
C3 C2 C1 . . 121.13(14)
C3 C2 H2 . . 119.4
C1 C2 H2 . . 119.4
C2 C3 C4 . . 117.21(13)
C2 C3 C8 . . 121.09(13)
C4 C3 C8 . . 121.66(13)
C5 C4 C3 . . 118.08(13)
C5 C4 C6 . . 119.03(12)
C3 C4 C6 . . 122.85(13)
N1 C5 C4 . . 123.17(12)
N1 C5 C5 . 2_657 117.45(8)
C4 C5 C5 . 2_657 119.38(8)
C6 C6 C4 2_657 . 121.49(8)
C6 C6 H6 2_657 . 119.3
C4 C6 H6 . . 119.3
C1 C7 H7A . . 109.5
C1 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C1 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C9 C8 C13 . . 118.73(14)
C9 C8 C3 . . 120.07(14)
C13 C8 C3 . . 121.20(13)
C10 C9 C8 . . 119.98(15)
C10 C9 H9 . . 120.0
C8 C9 H9 . . 120.0
C11 C10 C9 . . 120.69(16)
C11 C10 H10 . . 119.7
C9 C10 H10 . . 119.7
C12 C11 C10 . . 119.79(16)
C12 C11 H11 . . 120.1
C10 C11 H11 . . 120.1
C13 C12 C11 . . 119.84(16)
C13 C12 H12 . . 120.1
C11 C12 H12 . . 120.1
C12 C13 C8 . . 120.88(15)
C12 C13 H13 . . 119.6
C8 C13 H13 . . 119.6
C1 N1 C5 . . 117.69(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.3249(19)
C1 C2 . 1.401(2)
C1 C7 . 1.504(2)
C2 C3 . 1.368(2)
C2 H2 . 0.9300
C3 C4 . 1.4219(19)
C3 C8 . 1.489(2)
C4 C5 . 1.4030(19)
C4 C6 . 1.4281(19)
C5 N1 . 1.3599(17)
C5 C5 2_657 1.462(3)
C6 C6 2_657 1.347(3)
C6 H6 . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C9 . 1.3851(19)
C8 C13 . 1.394(2)
C9 C10 . 1.377(2)
C9 H9 . 0.9300
C10 C11 . 1.380(2)
C10 H10 . 0.9300
C11 C12 . 1.374(2)
C11 H11 . 0.9300
C12 C13 . 1.375(2)
C12 H12 . 0.9300
C13 H13 . 0.9300
