#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:58:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180282 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/68/7116890.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_7116890
loop_
_publ_author_name
'Ying Zhang'
'Jun-Hao Wang'
'Ji Zheng'
'Dan Li'
_publ_section_title
;
 A Br-substituted phenanthroimidazole derivative with aggregation induced
 emission from intermolecular halogen-hydrogen interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              6350
_journal_paper_doi               10.1039/C5cc00490J
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C29 H23 Br N2 S'
_chemical_formula_sum            'C29 H23 Br N2 S'
_chemical_formula_weight         511.46
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2014-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-01-15 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                99.988(5)
_cell_angle_beta                 101.997(6)
_cell_angle_gamma                95.944(5)
_cell_formula_units_Z            2
_cell_length_a                   9.2263(7)
_cell_length_b                   11.3952(5)
_cell_length_c                   12.1843(9)
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.4880
_cell_measurement_theta_min      3.2940
_cell_volume                     1221.01(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 10.4098
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_details
;
  1 omega  -50.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.7136  -57.0000  -30.0000 76

  2 omega  -47.00   81.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.7136    0.0000 -180.0000 128

  3 omega  -12.00   39.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.7136  -99.0000 -120.0000 51
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0487230000
_diffrn_orient_matrix_UB_12      -0.0018206000
_diffrn_orient_matrix_UB_13      0.0528287000
_diffrn_orient_matrix_UB_21      0.0590826000
_diffrn_orient_matrix_UB_22      -0.0086397000
_diffrn_orient_matrix_UB_23      -0.0282896000
_diffrn_orient_matrix_UB_31      0.0210932000
_diffrn_orient_matrix_UB_32      0.0632643000
_diffrn_orient_matrix_UB_33      0.0099484000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7668
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.080(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0513
_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)+(0.0756P)²+0.9747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                2582
_reflns_number_total             3492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc00490j2.cif
_cod_data_source_block           131005c
_cod_original_cell_volume        1221.01(14)
_cod_database_code               7116890
#BEGIN Tags that were not found in dictionaries:
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     20.77
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C24(H24), C4(H4), C1(H1), C3(H3), C17(H17), C18(H18), C25(H25),
 C22(H22), C13(H13), C14(H14), C2(H2), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br -0.01231(7) 0.82014(5) 0.02886(5) 0.0824(3) Uani 1 d . . .
S1 S 0.09154(14) 0.96901(10) 0.27575(10) 0.0565(4) Uani 1 d . . .
N1 N 0.1859(4) 1.1100(3) 0.5087(3) 0.0458(9) Uani 1 d . . .
N2 N -0.0009(4) 1.2200(3) 0.5151(3) 0.0425(8) Uani 1 d . . .
C20 C -0.1407(4) 1.2625(3) 0.4747(4) 0.0403(10) Uani 1 d . . .
C21 C -0.1423(5) 1.3522(4) 0.4136(4) 0.0511(11) Uani 1 d . . .
H21 H -0.0531 1.3918 0.4052 0.061 Uiso 1 calc . . R
C7 C 0.1020(5) 1.2566(3) 0.6199(4) 0.0417(10) Uani 1 d . . .
C15 C 0.0564(5) 1.1318(4) 0.4518(4) 0.0453(11) Uani 1 d . . .
C6 C 0.1048(5) 1.3459(3) 0.7197(4) 0.0433(10) Uani 1 d . . .
C9 C 0.3395(5) 1.1957(4) 0.7073(4) 0.0469(11) Uani 1 d . . .
C5 C 0.2302(5) 1.3590(4) 0.8127(4) 0.0452(10) Uani 1 d . . .
C16 C -0.0111(5) 1.0704(4) 0.3355(4) 0.0469(11) Uani 1 d . . .
C24 C -0.4060(5) 1.2399(4) 0.4423(4) 0.0531(12) Uani 1 d . . .
H24 H -0.4943 1.2019 0.4537 0.064 Uiso 1 calc . . R
C4 C 0.2398(6) 1.4491(4) 0.9089(4) 0.0591(12) Uani 1 d . . .
H4 H 0.3223 1.4599 0.9702 0.071 Uiso 1 calc . . R
C23 C -0.4131(5) 1.3276(4) 0.3763(4) 0.0463(11) Uani 1 d . . .
C8 C 0.2141(5) 1.1867(3) 0.6130(4) 0.0433(10) Uani 1 d . . .
C1 C -0.0073(5) 1.4199(4) 0.7296(4) 0.0528(11) Uani 1 d . . .
H1 H -0.0918 1.4102 0.6701 0.063 Uiso 1 calc . . R
C3 C 0.1322(6) 1.5213(5) 0.9154(5) 0.0665(14) Uani 1 d . . .
H3 H 0.1423 1.5813 0.9800 0.080 Uiso 1 calc . . R
C17 C -0.1421(6) 1.0718(4) 0.2585(4) 0.0610(13) Uani 1 d . . .
H17 H -0.2131 1.1205 0.2742 0.073 Uiso 1 calc . . R
C18 C -0.1582(6) 0.9919(5) 0.1527(4) 0.0679(14) Uani 1 d . . .
H18 H -0.2406 0.9822 0.0915 0.081 Uiso 1 calc . . R
C10 C 0.3465(5) 1.2808(4) 0.8077(4) 0.0487(11) Uani 1 d . . .
C25 C -0.2708(5) 1.2071(4) 0.4916(4) 0.0511(11) Uani 1 d . . .
H25 H -0.2684 1.1482 0.5357 0.061 Uiso 1 calc . . R
C22 C -0.2782(5) 1.3836(4) 0.3642(4) 0.0544(12) Uani 1 d . . .
H22 H -0.2790 1.4440 0.3217 0.065 Uiso 1 calc . . R
C13 C 0.5630(6) 1.1259(6) 0.7979(6) 0.0847(18) Uani 1 d . . .
H13 H 0.6355 1.0751 0.7953 0.102 Uiso 1 calc . . R
C14 C 0.4492(5) 1.1192(5) 0.7035(5) 0.0654(14) Uani 1 d . . .
H14 H 0.4447 1.0639 0.6366 0.079 Uiso 1 calc . . R
C2 C 0.0079(6) 1.5055(4) 0.8261(5) 0.0638(13) Uani 1 d . . .
H2 H -0.0666 1.5538 0.8317 0.077 Uiso 1 calc . . R
C26 C -0.5638(5) 1.3540(5) 0.3126(5) 0.0633(14) Uani 1 d . . .
C19 C -0.0412(6) 0.9316(4) 0.1506(4) 0.0573(13) Uani 1 d . . .
C11 C 0.4656(6) 1.2845(5) 0.9021(5) 0.0699(15) Uani 1 d . . .
H11 H 0.4736 1.3402 0.9693 0.084 Uiso 1 calc . . R
C12 C 0.5693(7) 1.2083(6) 0.8970(6) 0.0870(18) Uani 1 d . . .
H12 H 0.6456 1.2117 0.9613 0.104 Uiso 1 calc . . R
C27 C -0.5517(7) 1.4701(8) 0.2711(9) 0.147(4) Uani 1 d . . .
H27A H -0.5061 1.5349 0.3345 0.221 Uiso 1 calc . . GR
H27B H -0.6498 1.4848 0.2366 0.221 Uiso 1 calc . . GR
H27C H -0.4914 1.4652 0.2155 0.221 Uiso 1 calc . . GR
C29 C -0.6776(7) 1.3551(9) 0.3837(8) 0.138(4) Uani 1 d . . .
H29A H -0.6901 1.2793 0.4072 0.206 Uiso 1 calc . . GR
H29B H -0.7714 1.3681 0.3394 0.206 Uiso 1 calc . . GR
H29C H -0.6444 1.4187 0.4501 0.206 Uiso 1 calc . . GR
C28 C -0.6219(12) 1.2505(10) 0.2115(9) 0.186(5) Uani 1 d . . .
H28A H -0.5698 1.2601 0.1524 0.278 Uiso 1 calc . . GR
H28B H -0.7271 1.2497 0.1826 0.278 Uiso 1 calc . . GR
H28C H -0.6056 1.1760 0.2354 0.278 Uiso 1 calc . . GR
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'
Br Br -0.2901 2.4595 '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
C19 S1 C16 91.8(2) . .
C15 N1 C8 105.1(3) . .
C7 N2 C20 129.4(3) . .
C15 N2 C20 124.3(4) . .
C15 N2 C7 106.2(3) . .
C21 C20 N2 119.3(4) . .
C21 C20 C25 120.9(4) . .
C25 C20 N2 119.7(4) . .
C20 C21 H21 120.4 . .
C20 C21 C22 119.2(4) . .
C22 C21 H21 120.4 . .
N2 C7 C6 132.1(4) . .
C8 C7 N2 105.2(4) . .
C8 C7 C6 122.8(4) . .
N1 C15 N2 112.2(4) . .
N1 C15 C16 122.3(4) . .
N2 C15 C16 125.6(4) . .
C5 C6 C7 116.4(4) . .
C5 C6 C1 119.2(4) . .
C1 C6 C7 124.4(4) . .
C10 C9 C8 117.7(4) . .
C14 C9 C8 122.0(4) . .
C14 C9 C10 120.2(4) . .
C6 C5 C10 120.9(4) . .
C4 C5 C6 117.8(4) . .
C4 C5 C10 121.3(4) . .
C15 C16 S1 115.0(3) . .
C17 C16 S1 110.0(3) . .
C17 C16 C15 134.9(4) . .
C23 C24 H24 119.1 . .
C23 C24 C25 121.7(4) . .
C25 C24 H24 119.1 . .
C5 C4 H4 119.0 . .
C3 C4 C5 122.0(5) . .
C3 C4 H4 119.0 . .
C24 C23 C26 121.1(4) . .
C22 C23 C24 116.9(4) . .
C22 C23 C26 121.8(4) . .
N1 C8 C7 111.3(4) . .
N1 C8 C9 126.9(4) . .
C7 C8 C9 121.7(4) . .
C6 C1 H1 119.9 . .
C2 C1 C6 120.2(5) . .
C2 C1 H1 119.9 . .
C4 C3 H3 120.1 . .
C4 C3 C2 119.9(5) . .
C2 C3 H3 120.1 . .
C16 C17 H17 123.4 . .
C16 C17 C18 113.2(5) . .
C18 C17 H17 123.4 . .
C17 C18 H18 123.9 . .
C19 C18 C17 112.3(5) . .
C19 C18 H18 123.9 . .
C9 C10 C5 120.3(4) . .
C9 C10 C11 117.4(4) . .
C11 C10 C5 122.3(4) . .
C20 C25 C24 119.3(4) . .
C20 C25 H25 120.3 . .
C24 C25 H25 120.3 . .
C21 C22 H22 119.1 . .
C23 C22 C21 121.9(4) . .
C23 C22 H22 119.1 . .
C14 C13 H13 120.2 . .
C14 C13 C12 119.6(5) . .
C12 C13 H13 120.2 . .
C9 C14 H14 119.9 . .
C13 C14 C9 120.3(5) . .
C13 C14 H14 119.9 . .
C1 C2 C3 120.9(5) . .
C1 C2 H2 119.6 . .
C3 C2 H2 119.6 . .
C27 C26 C23 113.1(4) . .
C27 C26 C29 108.9(6) . .
C27 C26 C28 109.6(7) . .
C29 C26 C23 112.1(5) . .
C29 C26 C28 106.4(7) . .
C28 C26 C23 106.5(5) . .
S1 C19 Br1 120.1(3) . .
C18 C19 Br1 127.2(4) . .
C18 C19 S1 112.7(4) . .
C10 C11 H11 119.3 . .
C12 C11 C10 121.4(5) . .
C12 C11 H11 119.3 . .
C13 C12 H12 119.5 . .
C11 C12 C13 121.0(5) . .
C11 C12 H12 119.5 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C26 C29 H29A 109.5 . .
C26 C29 H29B 109.5 . .
C26 C29 H29C 109.5 . .
H29A C29 H29B 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C26 C28 H28A 109.5 . .
C26 C28 H28B 109.5 . .
C26 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C19 1.862(5) .
S1 C16 1.727(5) .
S1 C19 1.702(5) .
N1 C15 1.321(6) .
N1 C8 1.369(5) .
N2 C20 1.445(5) .
N2 C7 1.391(5) .
N2 C15 1.377(6) .
C20 C21 1.365(6) .
C20 C25 1.368(6) .
C21 H21 0.9300 .
C21 C22 1.384(6) .
C7 C6 1.438(6) .
C7 C8 1.377(6) .
C15 C16 1.444(6) .
C6 C5 1.416(6) .
C6 C1 1.411(6) .
C9 C8 1.432(6) .
C9 C10 1.408(6) .
C9 C14 1.405(6) .
C5 C4 1.399(6) .
C5 C10 1.468(6) .
C16 C17 1.370(7) .
C24 H24 0.9300 .
C24 C23 1.386(6) .
C24 C25 1.385(6) .
C4 H4 0.9300 .
C4 C3 1.360(7) .
C23 C22 1.387(6) .
C23 C26 1.532(6) .
C1 H1 0.9300 .
C1 C2 1.363(7) .
C3 H3 0.9300 .
C3 C2 1.379(7) .
C17 H17 0.9300 .
C17 C18 1.414(7) .
C18 H18 0.9300 .
C18 C19 1.341(7) .
C10 C11 1.407(7) .
C25 H25 0.9300 .
C22 H22 0.9300 .
C13 H13 0.9300 .
C13 C14 1.373(8) .
C13 C12 1.382(9) .
C14 H14 0.9300 .
C2 H2 0.9300 .
C26 C27 1.498(8) .
C26 C29 1.493(8) .
C26 C28 1.512(10) .
C11 H11 0.9300 .
C11 C12 1.361(8) .
C12 H12 0.9300 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
