#------------------------------------------------------------------------------
#$Date: 2017-05-06 00:39:52 +0300 (Sat, 06 May 2017) $
#$Revision: 196312 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/40/1544005.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_1544005
loop_
_publ_author_name
'Zhang, Jing Nan'
'Kang, Hui'
'Li, Nan'
'Zhou, Shi Ming'
'Sun, Hua Ming'
'Yin, Shi Wei'
'Zhao, Na'
'Tang, Ben Zhong'
_publ_section_title
;
 Organic solid fluorophores regulated by subtle structure modification:
 color-tunable and aggregation-induced emission.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              577
_journal_page_last               582
_journal_paper_doi               10.1039/c6sc02875f
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         '0.09(C28 H18 N4 O2)'
_chemical_formula_sum            'C2.545 H1.636 N0.364 O0.182'
_chemical_formula_weight         40.23
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2016-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                113.309(5)
_cell_angle_beta                 95.997(5)
_cell_angle_gamma                104.217(5)
_cell_formula_units_Z            11
_cell_length_a                   6.5174(4)
_cell_length_b                   9.8469(5)
_cell_length_c                   10.3476(5)
_cell_measurement_reflns_used    4977
_cell_measurement_theta_max      72.4360
_cell_measurement_theta_min      8.4320
_cell_volume                     575.83(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.9851
_diffrn_measured_fraction_theta_max 0.9851
_diffrn_measurement_details
;
  1 omega   -3.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 45

  2 omega   -3.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000   60.0000 43

  3 omega    1.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000    0.0000 28

  4 omega    0.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 34

  5 omega   78.00  103.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  152.0000  136.0000 25

  6 omega  -14.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -19.0000 -150.0000 109

  7 omega    3.00   76.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -57.0000   30.0000 73

  8 omega   63.00  127.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   37.0000 -150.0000 64

  9 omega  -12.00   78.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -77.0000  150.0000 90

 10 omega   25.00   98.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522  -99.0000  -60.0000 73

 11 omega   40.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -25.0000  120.0000 55

 12 omega  146.00  172.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   30.0000 26

 13 omega   49.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -37.0000  -90.0000 46

 14 omega   73.00  128.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000   90.0000 55

 15 omega   90.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   30.0000 36

 16 omega   92.00  149.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000  -30.0000 57

 17 omega   54.00   96.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -25.0000   60.0000 42

 18 omega   56.00  106.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -50.0000   30.0000 50

 19 omega   42.00  115.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000   90.0000 73

 20 omega   46.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000  -90.0000 49

 21 omega   44.00   95.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -37.0000 -150.0000 51

 22 omega   51.00  139.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -12.0000  -30.0000 88

 23 omega   55.00   81.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000 -180.0000 26

 24 omega  104.00  141.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -77.0000 -180.0000 37

 25 omega   78.00  149.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  -91.0000  -90.0000 71

 26 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000    0.0000 100

 27 omega  -74.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  152.0000  136.0000 60

 28 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000   90.0000 100

 29 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -150.0000 100

 30 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  150.0000 100

 31 omega   17.00  113.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522 -124.0000   30.0000 96

 32 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  -90.0000 100

 33 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000    0.0000 100

 34 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -180.0000 96

 35 omega   89.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   63.0000    0.0000 89

 36 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -90.0000 96

 37 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -150.0000 96

 38 omega   90.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   50.0000   60.0000 88

 39 omega   39.00  115.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044 -111.0000    0.0000 76

 40 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  120.0000 96

 41 omega   40.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   12.0000 -180.0000 138

 42 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000 -120.0000 96

 43 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -60.0000 96

 44 omega  -21.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 90

 45 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000  150.0000 98

 46 omega   17.00  113.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522 -124.0000 -150.0000 96

 47 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -120.0000 100

 48 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  -60.0000 100

 49 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000  120.0000 100

 50 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000   30.0000 100

 51 omega   26.00  126.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -       55.8522   77.0000 -180.0000 100

 52 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000   60.0000 96

 53 omega   56.00  150.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044  179.0000   30.0000 94

 54 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  150.0000 96

 55 omega   82.00  178.00   1.0000    3.2000
omega____ theta____ kappa____ phi______ frames
    -      111.7044   77.0000  -30.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0887718000
_diffrn_orient_matrix_UB_12      0.1792574000
_diffrn_orient_matrix_UB_13      0.0713465000
_diffrn_orient_matrix_UB_21      0.0096852000
_diffrn_orient_matrix_UB_22      -0.0027547000
_diffrn_orient_matrix_UB_23      -0.1491073000
_diffrn_orient_matrix_UB_31      -0.2338852000
_diffrn_orient_matrix_UB_32      0.0075853000
_diffrn_orient_matrix_UB_33      -0.0194477000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10627
_diffrn_reflns_theta_full        72.6743
_diffrn_reflns_theta_max         72.67
_diffrn_reflns_theta_min         4.78
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.2759
_exptl_crystal_description
;
;
_exptl_crystal_F_000             230.7271
_refine_diff_density_max         0.1426
_refine_diff_density_min         -0.2216
_refine_diff_density_rms         0.0432
_refine_ls_d_res_high            0.8076
_refine_ls_d_res_low             9.2561
_refine_ls_goodness_of_fit_ref   1.0717
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0717
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0614P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2024
_reflns_number_total             2254
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6sc02875f2.cif
_cod_data_source_block           exp_12595
_cod_depositor_comments
;Adding full bibliography for 1544005.cif.

 Adding full bibliography for 1544005.cif.
;
_cod_original_cell_volume        575.82(7)
_cod_database_code               1544005
_chemical_oxdiff_formula         'C O N'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C9(H9), C13(H13), C11(H11), C10(H10), C7(H7), C4(H4)
2.b Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_refinement_flags_posn
C1 C -0.4147(2) 0.56371(15) 0.86745(16) 0.0545(3) Uani 1.000000 .
C2 C -0.1724(2) 0.40530(14) 0.82205(15) 0.0495(3) Uani 1.000000 .
C3 C -0.1987(2) 0.55621(13) 0.86133(13) 0.0432(3) Uani 1.000000 .
C4 C -0.0263(2) 0.67879(13) 0.88877(13) 0.0427(3) Uani 1.000000 .
H4 H 0.1030(2) 0.65792(13) 0.87330(13) 0.0513(4) Uiso 1.000000 R
C5 C -0.01879(19) 0.84166(13) 0.94033(13) 0.0408(3) Uani 1.000000 .
C6 C 0.11689(19) 0.94020(13) 0.89375(13) 0.0410(3) Uani 1.000000 .
C7 C 0.1311(2) 1.09690(13) 0.95499(13) 0.0427(3) Uani 1.000000 .
H7 H 0.2189(2) 1.16315(13) 0.92488(13) 0.0513(3) Uiso 1.000000 R
C8 C 0.2385(2) 0.88243(13) 0.78138(13) 0.0428(3) Uani 1.000000 .
C9 C 0.1451(2) 0.74262(15) 0.65708(15) 0.0563(4) Uani 1.000000 .
H9 H 0.0036(2) 0.68255(15) 0.64496(15) 0.0676(4) Uiso 1.000000 R
C10 C 0.4489(2) 0.96916(14) 0.79374(14) 0.0486(3) Uani 1.000000 .
H10 H 0.5148(2) 1.06295(14) 0.87557(14) 0.0584(4) Uiso 1.000000 R
C11 C 0.5633(2) 0.92042(16) 0.68817(16) 0.0543(3) Uani 1.000000 .
H11 H 0.7038(2) 0.98115(16) 0.69894(16) 0.0652(4) Uiso 1.000000 R
C12 C 0.4672(2) 0.78045(16) 0.56624(16) 0.0566(4) Uani 1.000000 .
C13 C 0.2580(3) 0.69184(17) 0.55208(17) 0.0671(4) Uani 1.000000 .
H13 H 0.1933(3) 0.59723(17) 0.47092(17) 0.0805(5) Uiso 1.000000 R
C14 C 0.7474(3) 0.8239(2) 0.4431(2) 0.0822(5) Uani 1.000000 .
H14a H 0.7922(16) 0.7699(6) 0.3567(9) 0.1232(8) Uiso 1.000000 GR
H14b H 0.7099(8) 0.9106(10) 0.4388(17) 0.1232(8) Uiso 1.000000 GR
H14c H 0.8642(9) 0.8609(14) 0.5255(9) 0.1232(8) Uiso 1.000000 GR
N1 N -0.5857(2) 0.56818(18) 0.8731(2) 0.0837(5) Uani 1.000000 .
N2 N -0.1434(2) 0.28844(14) 0.79284(17) 0.0715(4) Uani 1.000000 .
O1 O 0.5643(2) 0.72095(14) 0.45541(13) 0.0806(4) Uani 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
N1 C1 C3 179.04(16) . .
N2 C2 C3 177.45(15) . .
C2 C3 C1 116.08(11) . .
C4 C3 C1 124.27(11) . .
C4 C3 C2 119.65(11) . .
C5 C4 C3 127.23(11) . .
C6 C5 C4 120.13(11) . .
C7 C5 C4 119.85(11) 2_577 .
C7 C5 C6 119.78(11) 2_577 .
C7 C6 C5 117.71(11) . .
C8 C6 C5 122.68(10) . .
C8 C6 C7 119.59(11) . .
C6 C7 C5 122.51(11) . 2_577
C9 C8 C6 121.80(11) . .
C10 C8 C6 120.87(11) . .
C10 C8 C9 117.29(12) . .
C13 C9 C8 121.28(12) . .
C11 C10 C8 122.04(12) . .
C12 C11 C10 119.49(12) . .
C13 C12 C11 119.41(13) . .
O1 C12 C11 124.58(13) . .
O1 C12 C13 116.01(13) . .
C12 C13 C9 120.49(13) . .
C14 O1 C12 117.87(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C3 1.4337(18) .
C1 N1 1.1330(18) .
C2 C3 1.4371(16) .
C2 N2 1.1378(17) .
C3 C4 1.3403(17) .
C4 C5 1.4622(16) .
C5 C6 1.4120(17) .
C5 C7 1.3925(17) 2_577
C6 C7 1.3910(16) .
C6 C8 1.4815(16) .
C8 C9 1.3942(17) .
C8 C10 1.3880(18) .
C9 C13 1.3749(19) .
C10 C11 1.3825(18) .
C11 C12 1.385(2) .
C12 C13 1.383(2) .
C12 O1 1.3643(16) .
C14 O1 1.417(2) .
