#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234621.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_7234621
loop_
_publ_author_name
'Shuzhen Li'
'Yanjun Lin'
'Dongpeng Yan'
_publ_section_title
;
 Two-component molecular cocrystals of 9-acetylanthracene with highly
 tunable one-/two-photon fluorescence and aggregation induced emission
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2527
_journal_page_last               2534
_journal_paper_doi               10.1039/C6TC00067C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 O, C10 H2 N4'
_chemical_formula_sum            'C26 H14 N4 O'
_chemical_formula_weight         398.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 95.710(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4098(14)
_cell_length_b                   8.1627(6)
_cell_length_c                   17.1171(11)
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    100.6
_cell_measurement_theta_max      29.5649
_cell_measurement_theta_min      2.9655
_cell_volume                     2003.4(3)
_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      100.6
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2918  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043 -131.0000  -93.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -47.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043  -37.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043   77.0000  -60.0000 82
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0419394000
_diffrn_orient_matrix_UB_12      -0.0459670000
_diffrn_orient_matrix_UB_13      0.0047471000
_diffrn_orient_matrix_UB_21      0.0261929000
_diffrn_orient_matrix_UB_22      0.0737173000
_diffrn_orient_matrix_UB_23      0.0015869000
_diffrn_orient_matrix_UB_31      -0.0008752000
_diffrn_orient_matrix_UB_32      0.0024883000
_diffrn_orient_matrix_UB_33      0.0413401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9790
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93225
_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_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0536
_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)+(0.0226P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                2488
_reflns_number_total             3922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-2527.cif
_cod_data_source_block           exp_3352
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7234621
_reflns_odcompleteness_completeness 99.73
_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+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
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
O1 O 0.24319(11) 0.67719(19) 0.34525(9) 0.0369(4) Uani 1 1 d . . .
N4 N 0.40823(13) 0.6197(2) -0.04913(10) 0.0258(5) Uani 1 1 d . . .
C22 C 0.26585(14) 0.3258(3) 0.02785(11) 0.0198(5) Uani 1 1 d . . .
H22 H 0.2377 0.4232 0.0447 0.024 Uiso 1 1 calc R . .
N3 N 0.52735(13) 0.2026(2) -0.12070(10) 0.0278(5) Uani 1 1 d . . .
N1 N 0.08520(14) 0.1609(2) 0.12403(11) 0.0346(5) Uani 1 1 d . . .
C2 C 0.16174(15) 0.3021(3) 0.33358(11) 0.0214(5) Uani 1 1 d . . .
C17 C 0.23044(14) 0.1740(3) 0.04619(11) 0.0195(5) Uani 1 1 d . . .
C1 C 0.21872(14) 0.4094(3) 0.29507(11) 0.0189(5) Uani 1 1 d . . .
C19 C 0.34779(14) 0.0389(3) -0.02313(11) 0.0205(5) Uani 1 1 d . . .
H19 H 0.3754 -0.0585 -0.0406 0.025 Uiso 1 1 calc R . .
C10 C 0.38787(15) 0.1193(3) 0.21646(11) 0.0238(5) Uani 1 1 d . . .
H10 H 0.4001 0.0050 0.2155 0.029 Uiso 1 1 calc R . .
C9 C 0.31155(15) 0.1782(3) 0.25569(11) 0.0209(5) Uani 1 1 d . . .
C12 C 0.42567(15) 0.3950(3) 0.18118(12) 0.0260(6) Uani 1 1 d . . .
H12 H 0.4648 0.4675 0.1560 0.031 Uiso 1 1 calc R . .
C25 C 0.46333(15) 0.1989(2) -0.08632(12) 0.0196(5) Uani 1 1 d . . .
N2 N 0.20714(14) -0.2567(2) 0.05189(11) 0.0336(5) Uani 1 1 d . . .
C20 C 0.38348(15) 0.1910(3) -0.04121(11) 0.0194(5) Uani 1 1 d . . .
C11 C 0.44350(15) 0.2243(3) 0.18035(11) 0.0270(6) Uani 1 1 d . . .
H11 H 0.4941 0.1832 0.1547 0.032 Uiso 1 1 calc R . .
C21 C 0.34256(14) 0.3353(3) -0.01531(11) 0.0180(5) Uani 1 1 d . . .
C14 C 0.29380(15) 0.3510(3) 0.25627(11) 0.0192(5) Uani 1 1 d . . .
C8 C 0.25526(14) 0.0723(3) 0.29451(11) 0.0221(5) Uani 1 1 d . . .
H8 H 0.2678 -0.0420 0.2944 0.027 Uiso 1 1 calc R . .
C13 C 0.35371(15) 0.4567(3) 0.21734(11) 0.0243(5) Uani 1 1 d . . .
H13 H 0.3429 0.5715 0.2168 0.029 Uiso 1 1 calc R . .
C23 C 0.14974(16) 0.1659(3) 0.09003(12) 0.0236(5) Uani 1 1 d . . .
C7 C 0.18120(15) 0.1302(3) 0.33334(11) 0.0210(5) Uani 1 1 d . . .
C24 C 0.23548(16) -0.1288(3) 0.03838(12) 0.0256(6) Uani 1 1 d . . .
C6 C 0.12406(15) 0.0228(3) 0.37420(11) 0.0275(6) Uani 1 1 d . . .
H6 H 0.1366 -0.0914 0.3753 0.033 Uiso 1 1 calc R . .
C15 C 0.19950(16) 0.5903(3) 0.29660(12) 0.0241(5) Uani 1 1 d . . .
C3 C 0.08607(14) 0.3596(3) 0.37459(11) 0.0252(5) Uani 1 1 d . . .
H3 H 0.0727 0.4735 0.3757 0.030 Uiso 1 1 calc R . .
C26 C 0.37901(15) 0.4935(3) -0.03441(11) 0.0194(5) Uani 1 1 d . . .
C4 C 0.03319(16) 0.2525(3) 0.41194(12) 0.0298(6) Uani 1 1 d . . .
H4 H -0.0169 0.2923 0.4387 0.036 Uiso 1 1 calc R . .
C16 C 0.12684(17) 0.6554(3) 0.23609(12) 0.0348(6) Uani 1 1 d . . .
H16A H 0.1206 0.7739 0.2430 0.052 Uiso 1 1 calc R . .
H16B H 0.0670 0.6022 0.2421 0.052 Uiso 1 1 calc R . .
H16C H 0.1453 0.6326 0.1836 0.052 Uiso 1 1 calc R . .
C5 C 0.05208(16) 0.0821(3) 0.41140(12) 0.0307(6) Uani 1 1 d . . .
H5 H 0.0141 0.0087 0.4373 0.037 Uiso 1 1 calc R . .
C18 C 0.27173(15) 0.0295(3) 0.02055(11) 0.0220(5) 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'
O O 0.0106 0.0060 '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
C17 C22 H22 120.0 . .
C17 C22 C21 119.9(2) . .
C21 C22 H22 120.0 . .
C1 C2 C7 119.01(19) . .
C1 C2 C3 122.2(2) . .
C7 C2 C3 118.8(2) . .
C22 C17 C23 119.36(19) . .
C22 C17 C18 120.03(19) . .
C18 C17 C23 120.59(19) . .
C2 C1 C15 119.07(19) . .
C14 C1 C2 121.4(2) . .
C14 C1 C15 119.50(19) . .
C20 C19 H19 120.1 . .
C18 C19 H19 120.1 . .
C18 C19 C20 119.9(2) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C11 C10 C9 121.1(2) . .
C10 C9 C14 118.76(19) . .
C8 C9 C10 121.7(2) . .
C8 C9 C14 119.53(19) . .
C11 C12 H12 119.4 . .
C13 C12 H12 119.4 . .
C13 C12 C11 121.1(2) . .
N3 C25 C20 178.4(2) . .
C19 C20 C25 119.25(19) . .
C19 C20 C21 120.07(19) . .
C21 C20 C25 120.68(19) . .
C10 C11 C12 119.9(2) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C22 C21 C20 120.05(19) . .
C22 C21 C26 119.72(19) . .
C20 C21 C26 120.23(18) . .
C1 C14 C9 118.85(19) . .
C1 C14 C13 122.9(2) . .
C13 C14 C9 118.25(19) . .
C9 C8 H8 119.2 . .
C7 C8 C9 121.6(2) . .
C7 C8 H8 119.2 . .
C12 C13 C14 120.9(2) . .
C12 C13 H13 119.6 . .
C14 C13 H13 119.6 . .
N1 C23 C17 179.1(3) . .
C2 C7 C6 118.45(19) . .
C8 C7 C2 119.56(19) . .
C8 C7 C6 122.0(2) . .
N2 C24 C18 179.0(2) . .
C7 C6 H6 119.5 . .
C5 C6 C7 120.9(2) . .
C5 C6 H6 119.5 . .
O1 C15 C1 119.96(19) . .
O1 C15 C16 123.0(2) . .
C16 C15 C1 117.01(19) . .
C2 C3 H3 119.7 . .
C4 C3 C2 120.6(2) . .
C4 C3 H3 119.7 . .
N4 C26 C21 179.6(2) . .
C3 C4 H4 119.6 . .
C3 C4 C5 120.7(2) . .
C5 C4 H4 119.6 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C6 C5 C4 120.5(2) . .
C6 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
C17 C18 C24 120.79(19) . .
C19 C18 C17 120.1(2) . .
C19 C18 C24 119.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C15 1.220(2) .
N4 C26 1.150(3) .
C22 H22 0.9500 .
C22 C17 1.388(3) .
C22 C21 1.392(3) .
N3 C25 1.143(3) .
N1 C23 1.146(3) .
C2 C1 1.409(3) .
C2 C7 1.431(3) .
C2 C3 1.433(3) .
C17 C23 1.447(3) .
C17 C18 1.411(3) .
C1 C14 1.408(3) .
C1 C15 1.503(3) .
C19 H19 0.9500 .
C19 C20 1.391(3) .
C19 C18 1.389(3) .
C10 H10 0.9500 .
C10 C9 1.428(3) .
C10 C11 1.363(3) .
C9 C14 1.434(3) .
C9 C8 1.398(3) .
C12 H12 0.9500 .
C12 C11 1.417(3) .
C12 C13 1.356(3) .
C25 C20 1.450(3) .
N2 C24 1.153(3) .
C20 C21 1.408(3) .
C11 H11 0.9500 .
C21 C26 1.444(3) .
C14 C13 1.431(3) .
C8 H8 0.9500 .
C8 C7 1.395(3) .
C13 H13 0.9500 .
C7 C6 1.432(3) .
C24 C18 1.438(3) .
C6 H6 0.9500 .
C6 C5 1.359(3) .
C15 C16 1.495(3) .
C3 H3 0.9500 .
C3 C4 1.361(3) .
C4 H4 0.9500 .
C4 C5 1.418(3) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C5 H5 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C22 C17 C23 N1 51(17) . . . .
C22 C17 C18 C19 0.0(3) . . . .
C22 C17 C18 C24 -179.44(19) . . . .
C22 C21 C26 N4 68(36) . . . .
N3 C25 C20 C19 -52(9) . . . .
N3 C25 C20 C21 128(9) . . . .
C2 C1 C14 C9 0.6(3) . . . .
C2 C1 C14 C13 -179.27(18) . . . .
C2 C1 C15 O1 96.4(3) . . . .
C2 C1 C15 C16 -84.4(2) . . . .
C2 C7 C6 C5 1.0(3) . . . .
C2 C3 C4 C5 0.3(3) . . . .
C17 C22 C21 C20 0.8(3) . . . .
C17 C22 C21 C26 179.86(18) . . . .
C1 C2 C7 C8 -0.6(3) . . . .
C1 C2 C7 C6 178.61(18) . . . .
C1 C2 C3 C4 -179.20(19) . . . .
C1 C14 C13 C12 179.51(19) . . . .
C19 C20 C21 C22 -0.5(3) . . . .
C19 C20 C21 C26 -179.59(18) . . . .
C10 C9 C14 C1 -179.85(18) . . . .
C10 C9 C14 C13 0.0(3) . . . .
C10 C9 C8 C7 179.48(19) . . . .
C9 C10 C11 C12 -0.2(3) . . . .
C9 C14 C13 C12 -0.3(3) . . . .
C9 C8 C7 C2 0.1(3) . . . .
C9 C8 C7 C6 -179.08(19) . . . .
C25 C20 C21 C22 179.91(18) . . . .
C25 C20 C21 C26 0.9(3) . . . .
N2 C24 C18 C17 165(100) . . . .
N2 C24 C18 C19 -14(18) . . . .
C20 C19 C18 C17 0.3(3) . . . .
C20 C19 C18 C24 179.71(19) . . . .
C20 C21 C26 N4 -113(36) . . . .
C11 C10 C9 C14 0.3(3) . . . .
C11 C10 C9 C8 -178.50(19) . . . .
C11 C12 C13 C14 0.4(3) . . . .
C21 C22 C17 C23 -179.02(18) . . . .
C21 C22 C17 C18 -0.5(3) . . . .
C14 C1 C15 O1 -82.7(3) . . . .
C14 C1 C15 C16 96.5(2) . . . .
C14 C9 C8 C7 0.7(3) . . . .
C8 C9 C14 C1 -1.0(3) . . . .
C8 C9 C14 C13 178.79(18) . . . .
C8 C7 C6 C5 -179.8(2) . . . .
C13 C12 C11 C10 -0.1(3) . . . .
C23 C17 C18 C19 178.44(18) . . . .
C23 C17 C18 C24 -1.0(3) . . . .
C7 C2 C1 C14 0.3(3) . . . .
C7 C2 C1 C15 -178.83(18) . . . .
C7 C2 C3 C4 -0.6(3) . . . .
C7 C6 C5 C4 -1.3(3) . . . .
C15 C1 C14 C9 179.66(18) . . . .
C15 C1 C14 C13 -0.2(3) . . . .
C3 C2 C1 C14 178.84(18) . . . .
C3 C2 C1 C15 -0.3(3) . . . .
C3 C2 C7 C8 -179.24(18) . . . .
C3 C2 C7 C6 0.0(3) . . . .
C3 C4 C5 C6 0.7(3) . . . .
C18 C17 C23 N1 -128(17) . . . .
C18 C19 C20 C25 179.53(18) . . . .
C18 C19 C20 C21 0.0(3) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339023
