#------------------------------------------------------------------------------
#$Date: 2020-04-14 00:17:29 +0300 (Tue, 14 Apr 2020) $
#$Revision: 250684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517564.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_4517564
loop_
_publ_author_name
'Xu, Letian'
'Zhou, Kun'
'Ma, Huili'
'Lv, Anqi'
'Pei, Dandan'
'Li, Guoping'
'Zhang, Yanfeng'
'An, Zhongfu'
'Li, Ang'
'He, Gang'
_publ_section_title
;
 Ultralong Organic Phosphorescent Nanocrystals with Long-Lived Triplet
 Excited States for Afterglow Imaging and Photodynamic Therapy.
;
_journal_name_full               'ACS applied materials & interfaces'
_journal_paper_doi               10.1021/acsami.0c04005
_journal_year                    2020
_chemical_formula_moiety         'C36 H24 N2 S'
_chemical_formula_sum            'C36 H24 N2 S'
_chemical_formula_weight         516.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 127.417(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.278(7)
_cell_length_b                   5.5097(13)
_cell_length_c                   20.597(5)
_cell_measurement_reflns_used    8011
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.566
_cell_measurement_theta_min      2.490
_cell_volume                     2548.8(11)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17965
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.689
_diffrn_reflns_theta_min         1.813
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+2.0465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             2959
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am0c04005_si_004.cif
_cod_data_source_block           a
_cod_original_cell_volume        2548.7(11)
_cod_database_code               4517564
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.926
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C15(H15), C5(H5), C18(H18), C16(H16), C11(H11),
 C17(H17), C9(H9), C8(H8), C10(H10)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.5000 1.18725(8) 0.7500 0.03103(14) Uani 1 2 d S T P . .
N1 N 0.35321(5) 0.5733(2) 0.44771(6) 0.0284(2) Uani 1 1 d . . . . .
C1 C 0.45974(6) 0.9898(2) 0.66405(7) 0.0243(3) Uani 1 1 d . . . . .
C6 C 0.45312(6) 1.0598(2) 0.59370(7) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.4731 1.2003 0.5949 0.033 Uiso 1 1 calc R . . . .
C13 C 0.33265(6) 0.2747(2) 0.35646(7) 0.0276(3) Uani 1 1 d . . . . .
C2 C 0.43148(6) 0.7795(2) 0.66231(7) 0.0264(3) Uani 1 1 d . . . . .
H2 H 0.4358 0.7302 0.7098 0.032 Uiso 1 1 calc R . . . .
C12 C 0.28589(6) 0.2752(2) 0.36574(7) 0.0286(3) Uani 1 1 d . . . . .
C14 C 0.37336(6) 0.4599(2) 0.40747(7) 0.0266(3) Uani 1 1 d . . . . .
C3 C 0.39717(6) 0.6424(2) 0.59138(8) 0.0269(3) Uani 1 1 d . . . . .
H3 H 0.3789 0.4971 0.5910 0.032 Uiso 1 1 calc R . . . .
C4 C 0.38921(5) 0.7165(2) 0.52033(7) 0.0253(3) Uani 1 1 d . . . . .
C7 C 0.29958(6) 0.4618(2) 0.42151(8) 0.0292(3) Uani 1 1 d . . . . .
C15 C 0.42452(6) 0.5029(2) 0.41385(8) 0.0306(3) Uani 1 1 d . . . . .
H15 H 0.4516 0.6281 0.4480 0.037 Uiso 1 1 calc R . . . .
C5 C 0.41742(6) 0.9253(2) 0.52187(7) 0.0282(3) Uani 1 1 d . . . . .
H5 H 0.4124 0.9764 0.4740 0.034 Uiso 1 1 calc R . . . .
C18 C 0.34402(6) 0.1293(3) 0.31142(8) 0.0331(3) Uani 1 1 d . . . . .
H18 H 0.3170 0.0044 0.2768 0.040 Uiso 1 1 calc R . . . .
C16 C 0.43469(7) 0.3558(3) 0.36839(8) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.4693 0.3819 0.3716 0.042 Uiso 1 1 calc R . . . .
C11 C 0.23403(6) 0.1382(3) 0.33121(8) 0.0352(3) Uani 1 1 d . . . . .
H11 H 0.2249 0.0084 0.2949 0.042 Uiso 1 1 calc R . . . .
C17 C 0.39514(7) 0.1706(3) 0.31817(8) 0.0369(3) Uani 1 1 d . . . . .
H17 H 0.4034 0.0720 0.2884 0.044 Uiso 1 1 calc R . . . .
C9 C 0.20969(7) 0.3856(3) 0.40433(9) 0.0414(4) Uani 1 1 d . . . . .
H9 H 0.1828 0.4234 0.4161 0.050 Uiso 1 1 calc R . . . .
C8 C 0.26143(6) 0.5204(3) 0.44056(9) 0.0384(3) Uani 1 1 d . . . . .
H8 H 0.2706 0.6490 0.4773 0.046 Uiso 1 1 calc R . . . .
C10 C 0.19626(7) 0.1945(3) 0.35061(9) 0.0397(3) Uani 1 1 d . . . . .
H10 H 0.1609 0.1028 0.3273 0.048 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'
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
_geom_angle_publ_flag
C1 S1 C1 104.59(8) . 2_656 ?
C14 N1 C4 125.16(11) . . ?
C7 N1 C14 107.98(11) . . ?
C7 N1 C4 124.01(11) . . ?
C6 C1 S1 117.67(10) . . ?
C2 C1 S1 122.92(9) . . ?
C2 C1 C6 119.26(11) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.54(12) . . ?
C5 C6 H6 119.7 . . ?
C14 C13 C12 107.30(11) . . ?
C18 C13 C12 133.13(13) . . ?
C18 C13 C14 119.53(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.16(11) . . ?
C3 C2 H2 119.9 . . ?
C7 C12 C13 106.77(12) . . ?
C11 C12 C13 133.76(13) . . ?
C11 C12 C7 119.46(13) . . ?
N1 C14 C13 108.66(12) . . ?
C15 C14 N1 129.75(12) . . ?
C15 C14 C13 121.57(12) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.50(12) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 N1 119.51(12) . . ?
C5 C4 N1 120.97(11) . . ?
C5 C4 C3 119.51(11) . . ?
N1 C7 C12 109.28(12) . . ?
C8 C7 N1 129.11(12) . . ?
C8 C7 C12 121.54(13) . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.68(13) . . ?
C16 C15 H15 121.2 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.99(11) . . ?
C4 C5 H5 120.0 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 119.00(13) . . ?
C17 C18 H18 120.5 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.49(14) . . ?
C17 C16 H16 119.3 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.13(13) . . ?
C10 C11 H11 120.4 . . ?
C18 C17 C16 120.72(13) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.21(14) . . ?
C10 C9 H9 119.4 . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 117.97(14) . . ?
C9 C8 H8 121.0 . . ?
C11 C10 C9 120.63(14) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7790(13) . ?
S1 C1 1.7791(12) 2_656 ?
N1 C14 1.4059(16) . ?
N1 C4 1.4304(16) . ?
N1 C7 1.4048(18) . ?
C1 C6 1.3977(17) . ?
C1 C2 1.3953(18) . ?
C6 H6 0.9500 . ?
C6 C5 1.3935(17) . ?
C13 C12 1.446(2) . ?
C13 C14 1.4142(18) . ?
C13 C18 1.4028(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3872(17) . ?
C12 C7 1.4091(18) . ?
C12 C11 1.399(2) . ?
C14 C15 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3994(18) . ?
C4 C5 1.3895(19) . ?
C7 C8 1.392(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.3941(18) . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.399(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(2) . ?
C17 H17 0.9500 . ?
C9 H9 0.9500 . ?
C9 C8 1.387(2) . ?
C9 C10 1.402(2) . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
