#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:53:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/42/1554205.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_1554205
loop_
_publ_author_name
'Peng, Zhe'
'Ji, Yingchun'
'Huang, Zihan'
'Tong, Bin'
'Shi, Jianbing'
'Dong, Yuping'
_publ_section_title
;
 A strategy for the molecular design of aggregation-induced emission units
 further modified by substituents
;
_journal_issue                   6
_journal_name_full               'Materials Chemistry Frontiers'
_journal_page_first              1175
_journal_paper_doi               10.1039/C8QM00096D
_journal_volume                  2
_journal_year                    2018
_chemical_formula_moiety         '2(C16 H10 N2)'
_chemical_formula_sum            'C32 H20 N4'
_chemical_formula_weight         460.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-05
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2017-04-18 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.209(10)
_cell_angle_beta                 98.460(10)
_cell_angle_gamma                102.006(10)
_cell_formula_units_Z            1
_cell_length_a                   6.0244(7)
_cell_length_b                   9.5199(11)
_cell_length_c                   10.6867(14)
_cell_measurement_reflns_used    839
_cell_measurement_temperature    102.4
_cell_measurement_theta_max      29.5482
_cell_measurement_theta_min      3.1753
_cell_volume                     585.20(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      102.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -120.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000    0.0000 90
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0485447000
_diffrn_orient_matrix_UB_12      -0.0150650000
_diffrn_orient_matrix_UB_13      -0.0662383000
_diffrn_orient_matrix_UB_21      0.0395392000
_diffrn_orient_matrix_UB_22      -0.0652880000
_diffrn_orient_matrix_UB_23      -0.0059898000
_diffrn_orient_matrix_UB_31      -0.1051332000
_diffrn_orient_matrix_UB_32      -0.0382990000
_diffrn_orient_matrix_UB_33      0.0141770000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3754
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0486
_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)+(0.0405P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                1746
_reflns_number_total             2302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qm00096d2.cif
_cod_data_source_block           exp_3317
_cod_original_cell_volume        585.20(12)
_cod_database_code               1554205
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.0395(2) 0.35108(15) 0.90334(14) 0.0173(3) Uani 1 1 d .
C7 C 0.5873(3) 0.35769(19) 0.56924(17) 0.0192(4) Uani 1 1 d .
C5 C 0.2401(3) 0.30555(18) 0.65726(17) 0.0190(4) Uani 1 1 d .
H5 H 0.0898 0.2521 0.6510 0.023 Uiso 1 1 calc R
C10 C 0.7136(3) 0.32826(19) 0.46765(18) 0.0208(4) Uani 1 1 d .
C6 C 0.3625(3) 0.27730(19) 0.56100(17) 0.0205(4) Uani 1 1 d .
H6 H 0.2952 0.2049 0.4910 0.025 Uiso 1 1 calc R
N2 N 0.8118(3) 0.30267(17) 0.38689(16) 0.0270(4) Uani 1 1 d .
C4 C 0.3390(3) 0.41366(18) 0.76424(17) 0.0169(4) Uani 1 1 d .
C11 C -0.0224(3) 0.19624(18) 0.86667(17) 0.0183(4) Uani 1 1 d .
C9 C 0.5648(3) 0.49301(18) 0.76996(17) 0.0181(4) Uani 1 1 d .
H9 H 0.6330 0.5651 0.8401 0.022 Uiso 1 1 calc R
C8 C 0.6883(3) 0.46686(18) 0.67426(17) 0.0193(4) Uani 1 1 d .
H8 H 0.8376 0.5214 0.6795 0.023 Uiso 1 1 calc R
C2 C 0.2115(3) 0.45119(18) 0.86489(16) 0.0173(4) Uani 1 1 d .
C12 C 0.1443(3) 0.1157(2) 0.88328(18) 0.0230(4) Uani 1 1 d .
H12 H 0.2956 0.1613 0.9211 0.028 Uiso 1 1 calc R
C16 C -0.2487(3) 0.1292(2) 0.81445(17) 0.0232(4) Uani 1 1 d .
H16 H -0.3598 0.1836 0.8050 0.028 Uiso 1 1 calc R
C13 C 0.0822(4) -0.0331(2) 0.84281(19) 0.0292(5) Uani 1 1 d .
H13 H 0.1931 -0.0878 0.8518 0.035 Uiso 1 1 calc R
C3 C 0.2236(3) 0.58978(18) 0.92901(17) 0.0182(4) Uani 1 1 d .
H3 H 0.3220 0.6762 0.9212 0.022 Uiso 1 1 calc R
C15 C -0.3088(3) -0.0213(2) 0.77594(19) 0.0313(5) Uani 1 1 d .
H15 H -0.4611 -0.0677 0.7413 0.038 Uiso 1 1 calc R
C14 C -0.1440(4) -0.1011(2) 0.7890(2) 0.0343(5) Uani 1 1 d .
H14 H -0.1844 -0.2012 0.7617 0.041 Uiso 1 1 calc R
C1 C -0.0560(3) 0.42786(18) 0.99173(17) 0.0175(4) Uani 1 1 d .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C11 127.83(13) . .
C1 N1 C11 124.52(14) . .
C1 N1 C2 107.54(13) . .
C6 C7 C10 119.47(16) . .
C6 C7 C8 120.12(15) . .
C8 C7 C10 120.41(15) . .
C6 C5 H5 119.5 . .
C6 C5 C4 121.03(16) . .
C4 C5 H5 119.5 . .
N2 C10 C7 178.90(18) . .
C7 C6 H6 120.1 . .
C5 C6 C7 119.80(16) . .
C5 C6 H6 120.1 . .
C5 C4 C2 122.59(15) . .
C9 C4 C5 117.99(15) . .
C9 C4 C2 119.33(15) . .
C12 C11 N1 120.09(16) . .
C16 C11 N1 118.99(15) . .
C16 C11 C12 120.92(16) . .
C4 C9 H9 119.2 . .
C8 C9 C4 121.63(16) . .
C8 C9 H9 119.2 . .
C7 C8 H8 120.3 . .
C9 C8 C7 119.43(16) . .
C9 C8 H8 120.3 . .
N1 C2 C4 123.92(15) . .
C3 C2 N1 109.12(14) . .
C3 C2 C4 126.72(16) . .
C11 C12 H12 120.5 . .
C13 C12 C11 119.06(18) . .
C13 C12 H12 120.5 . .
C11 C16 H16 120.4 . .
C11 C16 C15 119.19(18) . .
C15 C16 H16 120.4 . .
C12 C13 H13 119.8 . .
C12 C13 C14 120.39(18) . .
C14 C13 H13 119.8 . .
C2 C3 H3 127.1 . .
C2 C3 C1 105.76(15) . 2_567
C1 C3 H3 127.1 2_567 .
C16 C15 H15 119.9 . .
C14 C15 C16 120.24(19) . .
C14 C15 H15 119.9 . .
C13 C14 H14 119.9 . .
C15 C14 C13 120.16(18) . .
C15 C14 H14 119.9 . .
N1 C1 C3 142.43(15) . 2_567
C1 C1 N1 107.95(17) 2_567 .
C1 C1 C3 109.62(17) 2_567 2_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C11 1.431(2) .
N1 C2 1.401(2) .
N1 C1 1.385(2) .
C7 C10 1.446(2) .
C7 C6 1.394(2) .
C7 C8 1.398(2) .
C5 H5 0.9300 .
C5 C6 1.382(2) .
C5 C4 1.404(2) .
C10 N2 1.145(2) .
C6 H6 0.9300 .
C4 C9 1.400(2) .
C4 C2 1.461(2) .
C11 C12 1.389(2) .
C11 C16 1.379(2) .
C9 H9 0.9300 .
C9 C8 1.378(2) .
C8 H8 0.9300 .
C2 C3 1.391(2) .
C12 H12 0.9300 .
C12 C13 1.383(3) .
C16 H16 0.9300 .
C16 C15 1.394(3) .
C13 H13 0.9300 .
C13 C14 1.384(3) .
C3 H3 0.9300 .
C3 C1 1.408(2) 2_567
C15 H15 0.9300 .
C15 C14 1.373(3) .
C14 H14 0.9300 .
C1 C3 1.408(2) 2_567
C1 C1 1.375(3) 2_567
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
_geom_torsion_site_symmetry_4
N1 C11 C12 C13 -177.65(16) .
N1 C11 C16 C15 178.58(16) .
N1 C2 C3 C1 0.4(2) 2_567
C5 C4 C9 C8 -0.1(3) .
C5 C4 C2 N1 32.7(3) .
C5 C4 C2 C3 -141.15(19) .
C10 C7 C6 C5 -179.52(17) .
C10 C7 C8 C9 -179.98(16) .
C6 C7 C10 N2 -32(11) .
C6 C7 C8 C9 0.7(3) .
C6 C5 C4 C9 0.6(3) .
C6 C5 C4 C2 177.11(17) .
C4 C5 C6 C7 -0.4(3) .
C4 C9 C8 C7 -0.6(3) .
C4 C2 C3 C1 174.93(17) 2_567
C11 N1 C2 C4 8.9(3) .
C11 N1 C2 C3 -176.41(17) .
C11 N1 C1 C3 -2.8(4) 2_567
C11 N1 C1 C1 176.14(19) 2_567
C11 C12 C13 C14 -1.4(3) .
C11 C16 C15 C14 -0.5(3) .
C9 C4 C2 N1 -150.87(17) .
C9 C4 C2 C3 35.3(3) .
C8 C7 C10 N2 149(10) .
C8 C7 C6 C5 -0.2(3) .
C2 N1 C11 C12 54.3(3) .
C2 N1 C11 C16 -125.38(19) .
C2 N1 C1 C3 -179.4(2) 2_567
C2 N1 C1 C1 -0.5(2) 2_567
C2 C4 C9 C8 -176.71(16) .
C12 C11 C16 C15 -1.1(3) .
C12 C13 C14 C15 -0.3(3) .
C16 C11 C12 C13 2.1(3) .
C16 C15 C14 C13 1.2(3) .
C1 N1 C11 C12 -121.56(19) .
C1 N1 C11 C16 58.7(2) .
C1 N1 C2 C4 -174.70(16) .
C1 N1 C2 C3 0.0(2) .
