#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/60/7206058.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7206058
loop_
_publ_author_name
'Zhang, Ying'
'Lai, Shiu-Lun'
'Tong, Qing-Xiao'
'Chan, Mei-Yee'
'Ng, Tsz-Wai'
'Wen, Zhi-Chun'
'Zhang, Guo-Qiang'
'Lee, Shuit-Tong'
'Kwong, Hoi-Lun'
'Lee, Chun-Sing'
_publ_section_title
;
 Synthesis and characterization of phenanthroimidazole derivatives for
 applications in organic electroluminescent devices
;
_journal_issue                   22
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              8206
_journal_paper_doi               10.1039/c1jm10326a
_journal_volume                  21
_journal_year                    2011
_chemical_formula_sum            'C39 H30 N2 S'
_chemical_formula_weight         558.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.3580(10)
_cell_angle_beta                 97.9750(10)
_cell_angle_gamma                101.6110(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4051(8)
_cell_length_b                   11.1593(10)
_cell_length_c                   14.8250(13)
_cell_measurement_reflns_used    4921
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.1255
_cell_measurement_theta_min      2.26
_cell_volume                     1430.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Smart Apex CCD diffractometer'
_diffrn_measurement_method       '/f and /w 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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10113
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         4959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0427
_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)+(0.0815P)²+0.1972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                4234
_reflns_number_total             4959
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1jm10326a_1n-tpi.txt
_cod_data_source_block           1N-TPI
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7206058
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.47104(5) 0.56369(4) 0.29344(3) 0.04790(17) Uani 1 1 d . . .
N1 N 0.39321(15) 0.69215(13) 0.55969(9) 0.0396(3) Uani 1 1 d . . .
N2 N 0.30907(15) 0.50601(13) 0.43779(9) 0.0412(3) Uani 1 1 d . . .
C1 C 0.64706(18) 0.62522(16) 0.16995(11) 0.0414(4) Uani 1 1 d . . .
C2 C 0.23374(17) 0.50091(15) 0.51029(11) 0.0392(4) Uani 1 1 d . . .
C3 C 0.40371(17) 0.62079(15) 0.46924(11) 0.0385(4) Uani 1 1 d . . .
C4 C 0.28131(17) 0.61444(16) 0.58603(11) 0.0392(4) Uani 1 1 d . . .
C5 C 0.50420(17) 0.80326(15) 0.62461(11) 0.0386(4) Uani 1 1 d . . .
C6 C 0.61417(19) 0.78214(16) 0.68563(12) 0.0456(4) Uani 1 1 d . . .
H6 H 0.6155 0.6986 0.6843 0.055 Uiso 1 1 calc R . .
C7 C 0.63592(17) 0.70001(16) 0.10640(11) 0.0419(4) Uani 1 1 d . . .
C8 C 0.12066(18) 0.39495(16) 0.51225(12) 0.0421(4) Uani 1 1 d . . .
C9 C 0.21140(18) 0.64110(17) 0.66691(11) 0.0432(4) Uani 1 1 d . . .
C10 C 0.09090(19) 0.54123(18) 0.66648(12) 0.0454(4) Uani 1 1 d . . .
C11 C 0.50011(18) 0.66472(15) 0.41007(11) 0.0398(4) Uani 1 1 d . . .
C12 C 0.61005(18) 0.66550(16) 0.26638(12) 0.0417(4) Uani 1 1 d . . .
C13 C 0.05111(18) 0.41474(17) 0.59170(12) 0.0449(4) Uani 1 1 d . . .
C14 C 0.72445(19) 1.01311(16) 0.75272(11) 0.0441(4) Uani 1 1 d . . .
C15 C 0.67340(19) 0.65659(17) 0.01513(12) 0.0465(4) Uani 1 1 d . . .
C16 C 0.6125(2) 1.03062(17) 0.69004(13) 0.0489(4) Uani 1 1 d . . .
H16 H 0.6110 1.1139 0.6905 0.059 Uiso 1 1 calc R . .
C17 C 0.7219(2) 0.88602(18) 0.74860(12) 0.0494(4) Uani 1 1 d . . .
H17 H 0.7955 0.8711 0.7897 0.059 Uiso 1 1 calc R . .
C18 C 0.5027(2) 0.92697(17) 0.62663(12) 0.0476(4) Uani 1 1 d . . .
H18 H 0.4283 0.9411 0.5856 0.057 Uiso 1 1 calc R . .
C19 C 0.0811(2) 0.27479(17) 0.44030(13) 0.0502(4) Uani 1 1 d . . .
H19 H 0.1254 0.2634 0.3872 0.060 Uiso 1 1 calc R . .
C20 C 0.6737(2) 0.77182(18) 0.34410(13) 0.0509(4) Uani 1 1 d . . .
H20 H 0.7504 0.8385 0.3435 0.061 Uiso 1 1 calc R . .
C21 C 0.6904(2) 0.51314(18) 0.14073(13) 0.0519(5) Uani 1 1 d . . .
H21 H 0.6950 0.4634 0.1814 0.062 Uiso 1 1 calc R . .
C22 C 0.7213(2) 0.54194(19) -0.00980(13) 0.0561(5) Uani 1 1 d . . .
H22 H 0.7485 0.5143 -0.0687 0.067 Uiso 1 1 calc R . .
C23 C 0.2478(2) 0.76020(19) 0.74120(12) 0.0544(5) Uani 1 1 d . . .
H23 H 0.3280 0.8255 0.7427 0.065 Uiso 1 1 calc R . .
C24 C 0.5867(2) 0.81403(18) 0.12926(14) 0.0541(5) Uani 1 1 d . . .
H24 H 0.5628 0.8451 0.1888 0.065 Uiso 1 1 calc R . .
C25 C -0.0556(2) 0.3087(2) 0.59520(14) 0.0582(5) Uani 1 1 d . . .
H25 H -0.1040 0.3189 0.6464 0.070 Uiso 1 1 calc R . .
C26 C 0.61267(19) 0.77178(17) 0.42576(12) 0.0479(4) Uani 1 1 d . . .
H26 H 0.6456 0.8378 0.4843 0.058 Uiso 1 1 calc R . .
C27 C 0.0096(2) 0.5680(2) 0.73901(13) 0.0568(5) Uani 1 1 d . . .
H27 H -0.0713 0.5044 0.7390 0.068 Uiso 1 1 calc R . .
C28 C 0.8509(2) 1.12421(19) 0.82083(13) 0.0579(5) Uani 1 1 d . . .
C29 C 0.6590(2) 0.7275(2) -0.04922(14) 0.0608(5) Uani 1 1 d . . .
H29 H 0.6835 0.6993 -0.1089 0.073 Uiso 1 1 calc R . .
C30 C -0.0225(2) 0.17349(19) 0.44730(15) 0.0603(5) Uani 1 1 d . . .
H30 H -0.0470 0.0936 0.3996 0.072 Uiso 1 1 calc R . .
C31 C -0.0901(2) 0.1907(2) 0.52532(16) 0.0634(5) Uani 1 1 d . . .
H31 H -0.1594 0.1219 0.5305 0.076 Uiso 1 1 calc R . .
C32 C 0.0461(2) 0.6848(2) 0.80960(14) 0.0662(6) Uani 1 1 d . . .
H32 H -0.0100 0.6998 0.8567 0.079 Uiso 1 1 calc R . .
C33 C 0.7282(2) 0.4714(2) 0.05090(14) 0.0598(5) Uani 1 1 d . . .
H33 H 0.7582 0.3951 0.0329 0.072 Uiso 1 1 calc R . .
C34 C 0.1663(2) 0.7810(2) 0.81135(14) 0.0656(6) Uani 1 1 d . . .
H34 H 0.1919 0.8598 0.8603 0.079 Uiso 1 1 calc R . .
C35 C 0.6102(3) 0.8354(2) -0.02545(17) 0.0723(6) Uani 1 1 d . . .
H35 H 0.6007 0.8809 -0.0688 0.087 Uiso 1 1 calc R . .
C36 C 0.8186(3) 1.2560(2) 0.82945(17) 0.0789(7) Uani 1 1 d . . .
H36A H 0.7308 1.2604 0.8550 0.118 Uiso 1 1 calc R . .
H36B H 0.8039 1.2668 0.7671 0.118 Uiso 1 1 calc R . .
H36C H 0.9010 1.3232 0.8716 0.118 Uiso 1 1 calc R . .
C37 C 0.9900(2) 1.1200(3) 0.77958(18) 0.0821(7) Uani 1 1 d . . .
H37A H 1.0688 1.1938 0.8175 0.123 Uiso 1 1 calc R . .
H37B H 0.9701 1.1208 0.7145 0.123 Uiso 1 1 calc R . .
H37C H 1.0189 1.0426 0.7807 0.123 Uiso 1 1 calc R . .
C38 C 0.5740(3) 0.8792(2) 0.06423(17) 0.0701(6) Uani 1 1 d . . .
H38 H 0.5406 0.9540 0.0800 0.084 Uiso 1 1 calc R . .
C39 C 0.8746(4) 1.1130(3) 0.92178(16) 0.1048(10) Uani 1 1 d . . .
H39A H 0.9511 1.1857 0.9640 0.157 Uiso 1 1 calc R . .
H39B H 0.9036 1.0348 0.9200 0.157 Uiso 1 1 calc R . .
H39C H 0.7840 1.1115 0.9448 0.157 Uiso 1 1 calc R . .
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C11 92.67(8) . . ?
C3 N1 C4 105.93(13) . . ?
C3 N1 C5 125.84(13) . . ?
C4 N1 C5 125.53(13) . . ?
C3 N2 C2 105.24(13) . . ?
C21 C1 C7 119.29(15) . . ?
C21 C1 C12 119.24(15) . . ?
C7 C1 C12 121.46(15) . . ?
N2 C2 C4 111.11(14) . . ?
N2 C2 C8 127.22(15) . . ?
C4 C2 C8 121.67(15) . . ?
N2 C3 N1 112.34(14) . . ?
N2 C3 C11 121.63(14) . . ?
N1 C3 C11 125.95(14) . . ?
C2 C4 N1 105.38(13) . . ?
C2 C4 C9 123.03(15) . . ?
N1 C4 C9 131.31(15) . . ?
C18 C5 C6 120.16(15) . . ?
C18 C5 N1 122.02(14) . . ?
C6 C5 N1 117.82(14) . . ?
C17 C6 C5 119.38(16) . . ?
C17 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C24 C7 C15 118.17(16) . . ?
C24 C7 C1 123.01(16) . . ?
C15 C7 C1 118.80(15) . . ?
C19 C8 C13 120.26(16) . . ?
C19 C8 C2 122.41(16) . . ?
C13 C8 C2 117.32(15) . . ?
C23 C9 C10 119.20(16) . . ?
C23 C9 C4 124.67(16) . . ?
C10 C9 C4 115.99(15) . . ?
C27 C10 C9 117.86(17) . . ?
C27 C10 C13 121.08(17) . . ?
C9 C10 C13 121.05(15) . . ?
C26 C11 C3 134.02(15) . . ?
C26 C11 S1 110.18(12) . . ?
C3 C11 S1 115.80(12) . . ?
C20 C12 C1 130.65(16) . . ?
C20 C12 S1 110.22(13) . . ?
C1 C12 S1 119.05(12) . . ?
C25 C13 C8 117.04(17) . . ?
C25 C13 C10 122.65(17) . . ?
C8 C13 C10 120.30(15) . . ?
C16 C14 C17 116.83(16) . . ?
C16 C14 C28 123.23(17) . . ?
C17 C14 C28 119.88(17) . . ?
C29 C15 C22 121.42(17) . . ?
C29 C15 C7 119.37(17) . . ?
C22 C15 C7 119.20(16) . . ?
C14 C16 C18 121.61(17) . . ?
C14 C16 H16 119.2 . . ?
C18 C16 H16 119.2 . . ?
C6 C17 C14 122.19(16) . . ?
C6 C17 H17 118.9 . . ?
C14 C17 H17 118.9 . . ?
C5 C18 C16 119.83(16) . . ?
C5 C18 H18 120.1 . . ?
C16 C18 H18 120.1 . . ?
C30 C19 C8 120.65(18) . . ?
C30 C19 H19 119.7 . . ?
C8 C19 H19 119.7 . . ?
C12 C20 C26 113.86(16) . . ?
C12 C20 H20 123.1 . . ?
C26 C20 H20 123.1 . . ?
C1 C21 C33 121.56(17) . . ?
C1 C21 H21 119.2 . . ?
C33 C21 H21 119.2 . . ?
C33 C22 C15 120.89(17) . . ?
C33 C22 H22 119.6 . . ?
C15 C22 H22 119.6 . . ?
C34 C23 C9 120.72(19) . . ?
C34 C23 H23 119.6 . . ?
C9 C23 H23 119.6 . . ?
C38 C24 C7 120.30(19) . . ?
C38 C24 H24 119.8 . . ?
C7 C24 H24 119.8 . . ?
C31 C25 C13 121.88(19) . . ?
C31 C25 H25 119.1 . . ?
C13 C25 H25 119.1 . . ?
C11 C26 C20 113.06(15) . . ?
C11 C26 H26 123.5 . . ?
C20 C26 H26 123.5 . . ?
C32 C27 C10 121.78(19) . . ?
C32 C27 H27 119.1 . . ?
C10 C27 H27 119.1 . . ?
C37 C28 C39 111.1(2) . . ?
C37 C28 C14 107.72(15) . . ?
C39 C28 C14 110.84(17) . . ?
C37 C28 C36 108.17(18) . . ?
C39 C28 C36 107.15(19) . . ?
C14 C28 C36 111.86(18) . . ?
C35 C29 C15 120.94(19) . . ?
C35 C29 H29 119.5 . . ?
C15 C29 H29 119.5 . . ?
C19 C30 C31 119.81(19) . . ?
C19 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C25 C31 C30 120.32(18) . . ?
C25 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C27 C32 C34 120.21(19) . . ?
C27 C32 H32 119.9 . . ?
C34 C32 H32 119.9 . . ?
C22 C33 C21 120.21(18) . . ?
C22 C33 H33 119.9 . . ?
C21 C33 H33 119.9 . . ?
C23 C34 C32 120.18(19) . . ?
C23 C34 H34 119.9 . . ?
C32 C34 H34 119.9 . . ?
C29 C35 C38 120.10(19) . . ?
C29 C35 H35 120.0 . . ?
C38 C35 H35 120.0 . . ?
C28 C36 H36A 109.5 . . ?
C28 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C28 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C28 C37 H37A 109.5 . . ?
C28 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C28 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C24 C38 C35 121.1(2) . . ?
C24 C38 H38 119.4 . . ?
C35 C38 H38 119.4 . . ?
C28 C39 H39A 109.5 . . ?
C28 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C28 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C12 1.7221(17) . ?
S1 C11 1.7269(16) . ?
N1 C3 1.382(2) . ?
N1 C4 1.396(2) . ?
N1 C5 1.443(2) . ?
N2 C3 1.319(2) . ?
N2 C2 1.375(2) . ?
C1 C21 1.366(2) . ?
C1 C7 1.430(2) . ?
C1 C12 1.485(2) . ?
C2 C4 1.377(2) . ?
C2 C8 1.433(2) . ?
C3 C11 1.455(2) . ?
C4 C9 1.433(2) . ?
C5 C18 1.375(2) . ?
C5 C6 1.379(2) . ?
C6 C17 1.378(2) . ?
C6 H6 0.9300 . ?
C7 C24 1.409(2) . ?
C7 C15 1.422(2) . ?
C8 C19 1.399(2) . ?
C8 C13 1.410(2) . ?
C9 C23 1.409(2) . ?
C9 C10 1.418(2) . ?
C10 C27 1.403(2) . ?
C10 C13 1.467(3) . ?
C11 C26 1.367(2) . ?
C12 C20 1.359(2) . ?
C13 C25 1.408(3) . ?
C14 C16 1.387(3) . ?
C14 C17 1.397(3) . ?
C14 C28 1.529(2) . ?
C15 C29 1.409(3) . ?
C15 C22 1.410(3) . ?
C16 C18 1.387(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C30 1.375(3) . ?
C19 H19 0.9300 . ?
C20 C26 1.410(2) . ?
C20 H20 0.9300 . ?
C21 C33 1.402(3) . ?
C21 H21 0.9300 . ?
C22 C33 1.355(3) . ?
C22 H22 0.9300 . ?
C23 C34 1.371(3) . ?
C23 H23 0.9300 . ?
C24 C38 1.368(3) . ?
C24 H24 0.9300 . ?
C25 C31 1.370(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.365(3) . ?
C27 H27 0.9300 . ?
C28 C37 1.523(3) . ?
C28 C39 1.526(3) . ?
C28 C36 1.535(3) . ?
C29 C35 1.347(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(3) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C34 1.385(3) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C38 1.396(3) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26947393
