#------------------------------------------------------------------------------
#$Date: 2019-11-24 06:53:20 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/42/1554201.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_1554201
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                90.852(6)
_cell_angle_beta                 104.072(7)
_cell_angle_gamma                112.181(7)
_cell_formula_units_Z            1
_cell_length_a                   6.6509(6)
_cell_length_b                   7.9140(6)
_cell_length_c                   12.3019(11)
_cell_measurement_reflns_used    1368
_cell_measurement_temperature    102.3
_cell_measurement_theta_max      29.3193
_cell_measurement_theta_min      3.1002
_cell_volume                     577.49(9)
_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      102.3
_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  -46.00   42.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   83.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  3 omega   51.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -37.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega    8.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -37.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0655779000
_diffrn_orient_matrix_UB_12      -0.0907231000
_diffrn_orient_matrix_UB_13      -0.0271960000
_diffrn_orient_matrix_UB_21      0.0512997000
_diffrn_orient_matrix_UB_22      0.0212323000
_diffrn_orient_matrix_UB_23      -0.0450435000
_diffrn_orient_matrix_UB_31      0.0858148000
_diffrn_orient_matrix_UB_32      -0.0286460000
_diffrn_orient_matrix_UB_33      0.0285536000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4122
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96645
_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    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0419
_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)+(0.0322P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1848
_reflns_number_total             2262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qm00096d2.cif
_cod_data_source_block           exp_3313
_cod_original_cell_volume        577.48(8)
_cod_database_code               1554201
_reflns_odcompleteness_completeness 99.92
_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 0.50587(19) 0.65005(15) 0.10600(10) 0.0173(3) Uani 1 1 d .
C5 C 0.2127(2) 0.76631(19) 0.08112(13) 0.0191(3) Uani 1 1 d .
H5 H 0.1127 0.6573 0.0324 0.023 Uiso 1 1 calc R
C10 C 0.2042(2) 1.20262(19) 0.19074(13) 0.0201(3) Uani 1 1 d .
C6 C 0.1375(2) 0.90053(19) 0.10165(13) 0.0193(3) Uani 1 1 d .
H6 H -0.0142 0.8837 0.0675 0.023 Uiso 1 1 calc R
C8 C 0.5057(2) 1.08411(19) 0.22354(13) 0.0201(3) Uani 1 1 d .
H8 H 0.6051 1.1926 0.2728 0.024 Uiso 1 1 calc R
N2 N 0.1359(2) 1.31310(17) 0.20277(12) 0.0263(3) Uani 1 1 d .
C7 C 0.2841(2) 1.06124(18) 0.17266(12) 0.0184(3) Uani 1 1 d .
C9 C 0.5813(2) 0.95011(19) 0.20273(13) 0.0197(3) Uani 1 1 d .
H9 H 0.7329 0.9668 0.2369 0.024 Uiso 1 1 calc R
C4 C 0.4341(2) 0.78934(18) 0.13121(12) 0.0169(3) Uani 1 1 d .
C16 C 0.6351(3) 0.65827(19) 0.36818(13) 0.0219(3) Uani 1 1 d .
H16 H 0.4786 0.6291 0.3379 0.026 Uiso 1 1 calc R
C2 C 0.6698(2) 0.59647(18) 0.17411(13) 0.0180(3) Uani 1 1 d .
C1 C 0.4384(2) 0.55330(18) -0.00094(12) 0.0169(3) Uani 1 1 d .
C11 C 0.7665(2) 0.65309(18) 0.29615(13) 0.0185(3) Uani 1 1 d .
C3 C 0.7055(2) 0.47115(18) 0.11065(12) 0.0176(3) Uani 1 1 d .
H3 H 0.8069 0.4127 0.1356 0.021 Uiso 1 1 calc R
C12 C 0.9953(3) 0.6934(2) 0.34345(14) 0.0253(4) Uani 1 1 d .
H12 H 1.0872 0.6891 0.2961 0.030 Uiso 1 1 calc R
C15 C 0.7310(3) 0.7056(2) 0.48343(14) 0.0254(4) Uani 1 1 d .
H15 H 0.6403 0.7098 0.5315 0.030 Uiso 1 1 calc R
C13 C 1.0892(3) 0.7398(2) 0.45902(14) 0.0320(4) Uani 1 1 d .
H13 H 1.2450 0.7670 0.4902 0.038 Uiso 1 1 calc R
C14 C 0.9580(3) 0.7467(2) 0.52884(14) 0.0296(4) Uani 1 1 d .
H14 H 1.0233 0.7797 0.6078 0.036 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'
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 C4 129.05(12) . .
C1 N1 C4 123.34(12) . .
C1 N1 C2 107.25(11) . .
C6 C5 H5 119.8 . .
C6 C5 C4 120.40(13) . .
C4 C5 H5 119.8 . .
N2 C10 C7 178.25(16) . .
C5 C6 H6 120.0 . .
C5 C6 C7 119.98(13) . .
C7 C6 H6 120.0 . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C9 C8 C7 120.33(13) . .
C6 C7 C10 119.23(13) . .
C8 C7 C10 121.05(13) . .
C8 C7 C6 119.71(13) . .
C8 C9 H9 120.1 . .
C8 C9 C4 119.84(14) . .
C4 C9 H9 120.1 . .
C5 C4 N1 118.61(13) . .
C5 C4 C9 119.73(13) . .
C9 C4 N1 121.64(13) . .
C11 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C15 C16 C11 120.58(14) . .
N1 C2 C11 124.15(12) . .
C3 C2 N1 109.19(13) . .
C3 C2 C11 126.37(13) . .
N1 C1 C3 142.88(13) . 2_665
C1 C1 N1 107.91(16) 2_665 .
C1 C1 C3 109.19(16) 2_665 2_665
C16 C11 C2 122.29(13) . .
C12 C11 C16 118.37(14) . .
C12 C11 C2 119.24(13) . .
C2 C3 C1 106.45(12) . 2_665
C2 C3 H3 126.8 . .
C1 C3 H3 126.8 2_665 .
C11 C12 H12 119.7 . .
C13 C12 C11 120.53(15) . .
C13 C12 H12 119.7 . .
C16 C15 H15 119.8 . .
C14 C15 C16 120.36(15) . .
C14 C15 H15 119.8 . .
C12 C13 H13 119.8 . .
C14 C13 C12 120.42(15) . .
C14 C13 H13 119.8 . .
C15 C14 H14 120.1 . .
C13 C14 C15 119.74(16) . .
C13 C14 H14 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C4 1.4136(17) .
N1 C2 1.4091(18) .
N1 C1 1.3936(18) .
C5 H5 0.9500 .
C5 C6 1.3774(19) .
C5 C4 1.3906(19) .
C10 N2 1.1494(18) .
C10 C7 1.4432(19) .
C6 H6 0.9500 .
C6 C7 1.396(2) .
C8 H8 0.9500 .
C8 C7 1.394(2) .
C8 C9 1.3783(19) .
C9 H9 0.9500 .
C9 C4 1.400(2) .
C16 H16 0.9500 .
C16 C11 1.398(2) .
C16 C15 1.386(2) .
C2 C11 1.470(2) .
C2 C3 1.377(2) .
C1 C1 1.377(3) 2_665
C1 C3 1.414(2) 2_665
C11 C12 1.397(2) .
C3 C1 1.414(2) 2_665
C3 H3 0.9500 .
C12 H12 0.9500 .
C12 C13 1.388(2) .
C15 H15 0.9500 .
C15 C14 1.382(2) .
C13 H13 0.9500 .
C13 C14 1.379(2) .
C14 H14 0.9500 .
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 C2 C11 C16 41.8(2) .
N1 C2 C11 C12 -141.87(14) .
N1 C2 C3 C1 0.15(16) 2_665
C5 C6 C7 C10 178.29(13) .
C5 C6 C7 C8 -0.7(2) .
C6 C5 C4 N1 -178.66(13) .
C6 C5 C4 C9 -0.1(2) .
C8 C9 C4 N1 178.82(13) .
C8 C9 C4 C5 0.3(2) .
N2 C10 C7 C6 -15(5) .
N2 C10 C7 C8 164(5) .
C7 C8 C9 C4 -0.7(2) .
C9 C8 C7 C10 -178.05(13) .
C9 C8 C7 C6 0.9(2) .
C4 N1 C2 C11 13.4(2) .
C4 N1 C2 C3 -172.38(12) .
C4 N1 C1 C1 172.24(14) 2_665
C4 N1 C1 C3 -5.4(3) 2_665
C4 C5 C6 C7 0.3(2) .
C16 C11 C12 C13 -0.8(2) .
C16 C15 C14 C13 -0.3(2) .
C2 N1 C4 C5 -149.57(14) .
C2 N1 C4 C9 31.9(2) .
C2 N1 C1 C1 -1.38(18) 2_665
C2 N1 C1 C3 -179.03(18) 2_665
C2 C11 C12 C13 -177.31(13) .
C1 N1 C4 C5 38.28(18) .
C1 N1 C4 C9 -140.23(14) .
C1 N1 C2 C11 -173.43(12) .
C1 N1 C2 C3 0.76(15) .
C11 C16 C15 C14 -0.6(2) .
C11 C2 C3 C1 174.18(13) 2_665
C11 C12 C13 C14 0.0(2) .
C3 C2 C11 C16 -131.36(16) .
C3 C2 C11 C12 45.0(2) .
C12 C13 C14 C15 0.6(2) .
C15 C16 C11 C2 177.50(13) .
C15 C16 C11 C12 1.2(2) .
