#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/97/2229759.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_2229759
loop_
_publ_author_name
'Ma, Ling'
'Lu, Liping'
'Zhu, Miaoli'
_publ_section_title
;
 2-(4-Methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
;
_journal_coeditor_code           LW2058
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o864
_journal_page_last               o865
_journal_paper_doi               10.1107/S1600536811008853
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H14 N4'
_chemical_formula_moiety         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_chemical_name_systematic
;
2-(4-Methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline
;
_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                 108.8920(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1609(8)
_cell_length_b                   15.5398(13)
_cell_length_c                   11.7250(10)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.47
_cell_volume                     1579.2(2)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and SHELXTL/PC (Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10917
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0373
_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)+(0.0470P)²+0.4106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                2182
_reflns_number_total             2790
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lw2058.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229759
_cod_database_fobs_code          2229759
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1494(2) 0.34388(11) 0.29392(16) 0.0569(5) Uani d . 1 . .
H H1 0.0796 0.3893 0.2775 0.068 Uiso calc R 1 . .
C C2 0.2314(2) 0.32622(12) 0.41361(15) 0.0600(5) Uani d . 1 . .
H H2 0.2142 0.3582 0.4751 0.072 Uiso calc R 1 . .
C C3 0.3377(2) 0.26132(11) 0.43997(14) 0.0497(4) Uani d . 1 . .
H H3 0.3958 0.2495 0.5195 0.060 Uiso calc R 1 . .
C C4 0.35793(17) 0.21310(9) 0.34572(13) 0.0394(4) Uani d . 1 . .
C C5 0.26563(18) 0.23316(10) 0.22634(13) 0.0413(4) Uani d . 1 . .
C C6 0.27420(18) 0.18067(10) 0.12531(13) 0.0424(4) Uani d . 1 . .
C C7 0.37132(17) 0.10795(10) 0.14623(13) 0.0405(4) Uani d . 1 . .
C C8 0.3685(2) 0.05668(11) 0.04748(14) 0.0506(4) Uani d . 1 . .
H H8 0.4290 0.0073 0.0587 0.061 Uiso calc R 1 . .
C C9 0.2767(2) 0.07936(12) -0.06532(15) 0.0607(5) Uani d . 1 . .
H H9 0.2740 0.0464 -0.1321 0.073 Uiso calc R 1 . .
C C10 0.1872(2) 0.15308(12) -0.07761(15) 0.0635(5) Uani d . 1 . .
H H10 0.1256 0.1686 -0.1548 0.076 Uiso calc R 1 . .
C C11 0.46288(17) 0.14274(10) 0.36043(13) 0.0386(4) Uani d . 1 . .
C C12 0.46786(17) 0.09098(10) 0.26710(13) 0.0390(4) Uani d . 1 . .
C C13 0.63601(17) 0.04011(10) 0.42481(13) 0.0415(4) Uani d . 1 . .
C C14 0.76079(17) -0.01205(10) 0.50460(13) 0.0433(4) Uani d . 1 . .
C C15 0.8293(2) -0.07558(12) 0.45554(16) 0.0549(5) Uani d . 1 . .
H H15 0.7935 -0.0854 0.3728 0.066 Uiso calc R 1 . .
C C16 0.9495(2) -0.12424(13) 0.52785(17) 0.0615(5) Uani d . 1 . .
H H16 0.9942 -0.1658 0.4926 0.074 Uiso calc R 1 . .
C C17 1.0053(2) -0.11301(13) 0.65087(16) 0.0567(5) Uani d . 1 . .
C C18 0.9361(2) -0.05052(13) 0.69982(16) 0.0600(5) Uani d . 1 . .
H H18 0.9709 -0.0419 0.7828 0.072 Uiso calc R 1 . .
C C19 0.8162(2) -0.00045(12) 0.62845(15) 0.0538(4) Uani d . 1 . .
H H19 0.7725 0.0414 0.6639 0.065 Uiso calc R 1 . .
C C20 1.1369(2) -0.16699(15) 0.7291(2) 0.0798(7) Uani d . 1 . .
H H20A 1.2040 -0.1317 0.7914 0.120 Uiso calc R 1 . .
H H20B 1.1938 -0.1907 0.6806 0.120 Uiso calc R 1 . .
H H20C 1.0966 -0.2129 0.7649 0.120 Uiso calc R 1 . .
N N1 0.16445(16) 0.29995(9) 0.20174(12) 0.0501(4) Uani d . 1 . .
N N2 0.18375(17) 0.20271(9) 0.01305(12) 0.0560(4) Uani d . 1 . .
N N3 0.57503(14) 0.02646(8) 0.30708(11) 0.0433(3) Uani d . 1 . .
N N4 0.57054(15) 0.10950(8) 0.46160(11) 0.0416(3) Uani d . 1 . .
H H4 0.603(2) 0.1350(12) 0.5353(17) 0.062(5) Uiso 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
_geom_angle_publ_flag
N1 C1 C2 . . 123.95(16) ?
N1 C1 H1 . . 118.0 ?
C2 C1 H1 . . 118.0 ?
C3 C2 C1 . . 119.18(16) ?
C3 C2 H2 . . 120.4 ?
C1 C2 H2 . . 120.4 ?
C2 C3 C4 . . 118.99(15) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 118.32(14) ?
C3 C4 C11 . . 124.86(14) ?
C5 C4 C11 . . 116.79(13) ?
N1 C5 C4 . . 121.73(14) ?
N1 C5 C6 . . 117.80(13) ?
C4 C5 C6 . . 120.46(14) ?
N2 C6 C7 . . 121.69(14) ?
N2 C6 C5 . . 118.08(14) ?
C7 C6 C5 . . 120.20(13) ?
C8 C7 C6 . . 118.11(14) ?
C8 C7 C12 . . 123.68(14) ?
C6 C7 C12 . . 118.22(13) ?
C9 C8 C7 . . 119.71(16) ?
C9 C8 H8 . . 120.1 ?
C7 C8 H8 . . 120.1 ?
C8 C9 C10 . . 118.15(16) ?
C8 C9 H9 . . 120.9 ?
C10 C9 H9 . . 120.9 ?
N2 C10 C9 . . 124.39(16) ?
N2 C10 H10 . . 117.8 ?
C9 C10 H10 . . 117.8 ?
C12 C11 N4 . . 105.57(13) ?
C12 C11 C4 . . 123.21(13) ?
N4 C11 C4 . . 131.17(14) ?
C11 C12 N3 . . 111.12(13) ?
C11 C12 C7 . . 120.85(14) ?
N3 C12 C7 . . 128.03(13) ?
N3 C13 N4 . . 111.93(13) ?
N3 C13 C14 . . 123.65(14) ?
N4 C13 C14 . . 124.41(14) ?
C19 C14 C15 . . 117.68(15) ?
C19 C14 C13 . . 122.85(16) ?
C15 C14 C13 . . 119.47(14) ?
C16 C15 C14 . . 120.86(17) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C17 C16 C15 . . 121.78(19) ?
C17 C16 H16 . . 119.1 ?
C15 C16 H16 . . 119.1 ?
C16 C17 C18 . . 117.37(16) ?
C16 C17 C20 . . 121.20(19) ?
C18 C17 C20 . . 121.43(18) ?
C17 C18 C19 . . 121.64(17) ?
C17 C18 H18 . . 119.2 ?
C19 C18 H18 . . 119.2 ?
C18 C19 C14 . . 120.66(18) ?
C18 C19 H19 . . 119.7 ?
C14 C19 H19 . . 119.7 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C1 N1 C5 . . 117.73(14) ?
C10 N2 C6 . . 117.91(15) ?
C13 N3 C12 . . 104.57(13) ?
C13 N4 C11 . . 106.80(13) ?
C13 N4 H4 . . 127.0(12) ?
C11 N4 H4 . . 125.3(12) ?
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
C1 N1 . 1.323(2) ?
C1 C2 . 1.388(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.366(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.396(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.416(2) ?
C4 C11 . 1.429(2) ?
C5 N1 . 1.359(2) ?
C5 C6 . 1.461(2) ?
C6 N2 . 1.3528(19) ?
C6 C7 . 1.410(2) ?
C7 C8 . 1.399(2) ?
C7 C12 . 1.431(2) ?
C8 C9 . 1.364(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.389(3) ?
C9 H9 . 0.9300 ?
C10 N2 . 1.322(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.371(2) ?
C11 N4 . 1.3744(19) ?
C12 N3 . 1.3751(19) ?
C13 N3 . 1.3278(19) ?
C13 N4 . 1.370(2) ?
C13 C14 . 1.465(2) ?
C14 C19 . 1.386(2) ?
C14 C15 . 1.390(2) ?
C15 C16 . 1.378(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.376(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.382(3) ?
C17 C20 . 1.511(2) ?
C18 C19 . 1.384(2) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
N4 H4 . 0.908(19) ?
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
N4 H4 N1 4_666 0.908(19) 2.106(19) 3.0131(19) 176.0(17) y
C1 H1 N3 2_555 0.93 2.57 3.479(2) 165 y
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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 C3 . . . . 1.8(3) ?
C1 C2 C3 C4 . . . . -1.7(3) ?
C2 C3 C4 C5 . . . . -0.6(2) ?
C2 C3 C4 C11 . . . . -178.91(16) ?
C3 C4 C5 N1 . . . . 3.1(2) ?
C11 C4 C5 N1 . . . . -178.52(14) ?
C3 C4 C5 C6 . . . . -175.51(14) ?
C11 C4 C5 C6 . . . . 2.9(2) ?
N1 C5 C6 N2 . . . . 1.5(2) ?
C4 C5 C6 N2 . . . . -179.89(14) ?
N1 C5 C6 C7 . . . . -176.74(14) ?
C4 C5 C6 C7 . . . . 1.9(2) ?
N2 C6 C7 C8 . . . . -2.1(2) ?
C5 C6 C7 C8 . . . . 176.11(15) ?
N2 C6 C7 C12 . . . . 177.60(14) ?
C5 C6 C7 C12 . . . . -4.2(2) ?
C6 C7 C8 C9 . . . . 1.9(3) ?
C12 C7 C8 C9 . . . . -177.75(16) ?
C7 C8 C9 C10 . . . . -0.6(3) ?
C8 C9 C10 N2 . . . . -0.6(3) ?
C3 C4 C11 C12 . . . . 172.70(15) ?
C5 C4 C11 C12 . . . . -5.6(2) ?
C3 C4 C11 N4 . . . . -4.5(3) ?
C5 C4 C11 N4 . . . . 177.23(15) ?
N4 C11 C12 N3 . . . . 0.13(17) ?
C4 C11 C12 N3 . . . . -177.65(13) ?
N4 C11 C12 C7 . . . . -178.88(13) ?
C4 C11 C12 C7 . . . . 3.3(2) ?
C8 C7 C12 C11 . . . . -178.62(15) ?
C6 C7 C12 C11 . . . . 1.7(2) ?
C8 C7 C12 N3 . . . . 2.6(3) ?
C6 C7 C12 N3 . . . . -177.08(14) ?
N3 C13 C14 C19 . . . . -175.68(15) ?
N4 C13 C14 C19 . . . . 5.7(2) ?
N3 C13 C14 C15 . . . . 5.1(2) ?
N4 C13 C14 C15 . . . . -173.46(15) ?
C19 C14 C15 C16 . . . . -0.9(3) ?
C13 C14 C15 C16 . . . . 178.34(16) ?
C14 C15 C16 C17 . . . . 0.9(3) ?
C15 C16 C17 C18 . . . . -0.1(3) ?
C15 C16 C17 C20 . . . . 179.85(17) ?
C16 C17 C18 C19 . . . . -0.5(3) ?
C20 C17 C18 C19 . . . . 179.49(17) ?
C17 C18 C19 C14 . . . . 0.5(3) ?
C15 C14 C19 C18 . . . . 0.3(3) ?
C13 C14 C19 C18 . . . . -178.97(15) ?
C2 C1 N1 C5 . . . . 0.6(3) ?
C4 C5 N1 C1 . . . . -3.0(2) ?
C6 C5 N1 C1 . . . . 175.60(15) ?
C9 C10 N2 C6 . . . . 0.5(3) ?
C7 C6 N2 C10 . . . . 0.9(3) ?
C5 C6 N2 C10 . . . . -177.34(17) ?
N4 C13 N3 C12 . . . . 1.02(17) ?
C14 C13 N3 C12 . . . . -177.72(14) ?
C11 C12 N3 C13 . . . . -0.70(17) ?
C7 C12 N3 C13 . . . . 178.22(15) ?
N3 C13 N4 C11 . . . . -0.97(17) ?
C14 C13 N4 C11 . . . . 177.76(14) ?
C12 C11 N4 C13 . . . . 0.48(16) ?
C4 C11 N4 C13 . . . . 178.01(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21377789
