#------------------------------------------------------------------------------
#$Date: 2019-11-10 01:23:14 +0200 (Sun, 10 Nov 2019) $
#$Revision: 225524 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/53/4515371.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_4515371
loop_
_publ_author_name
'Song, Inho'
'Lee, Seung-Chul'
'Shang, Xiaobo'
'Ahn, Jaeyong'
'Jung, Hoon-Joo'
'Jeong, Chan-Uk'
'Kim, Sang-Wook'
'Yoon, Woojin'
'Yun, Hoseop'
'Kwon, O-Pil'
'Oh, Joon Hak'
_publ_section_title
;
 High-Performance Visible-Blind UV Phototransistors Based on n-Type
 Naphthalene Diimide Nanomaterials.
;
_journal_issue                   14
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              11826
_journal_page_last               11836
_journal_paper_doi               10.1021/acsami.8b01500
_journal_volume                  10
_journal_year                    2018
_chemical_formula_sum            'C12 H7 N O2 S'
_chemical_formula_weight         229.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-10 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 95.6420(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1040(4)
_cell_length_b                   4.4160(2)
_cell_length_c                   27.7650(13)
_cell_measurement_reflns_used    5829
_cell_measurement_temperature    290(1)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      3.19
_cell_volume                     988.82(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      290(1)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-axis Rapid S'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.190
_diffrn_source                   'Sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Brightyellow
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       Needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0525P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1513
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am8b01500_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4515371
_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.
;
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
S1 S 0.41465(6) 0.34416(13) 0.84635(2) 0.0602(2) Uani 1 1 d . .
O1 O 1.01117(17) 0.2224(4) 0.85360(5) 0.0683(4) Uani 1 1 d . .
O2 O 0.62190(17) 0.5892(4) 0.94471(5) 0.0707(4) Uani 1 1 d . .
N1 N 0.81781(17) 0.4085(3) 0.89960(5) 0.0490(4) Uani 1 1 d . .
C4 C 1.0341(2) 0.0653(4) 0.93529(6) 0.0458(4) Uani 1 1 d . .
C2 C 0.8198(2) 0.2569(4) 0.98442(7) 0.0464(4) Uani 1 1 d . .
C3 C 0.96318(19) 0.0806(4) 0.97988(6) 0.0433(4) Uani 1 1 d . .
C5 C 1.1748(2) -0.1070(5) 0.93190(7) 0.0533(5) Uani 1 1 d . .
H5 H 1.2215 -0.1169 0.9027 0.064 Uiso 1 1 calc R U
C7 C 0.9574(2) 0.2330(4) 0.89267(7) 0.0508(5) Uani 1 1 d . .
C6 C 0.7436(2) 0.4294(4) 0.94272(7) 0.0510(5) Uani 1 1 d . .
C1 C 0.7523(2) 0.2663(5) 1.02811(7) 0.0548(5) Uani 1 1 d . .
H1 H 0.6572 0.3800 1.0309 0.066 Uiso 1 1 calc R U
C8 C 0.7390(2) 0.5781(4) 0.85705(7) 0.0546(5) Uani 1 1 d . .
H8A H 0.8237 0.6367 0.8365 0.066 Uiso 1 1 calc R U
H8B H 0.6889 0.7615 0.8682 0.066 Uiso 1 1 calc R U
C10 C 0.6234(2) 0.2524(5) 0.78545(7) 0.0546(5) Uani 1 1 d . .
H10 H 0.7197 0.2533 0.7698 0.065 Uiso 1 1 calc R U
C9 C 0.6092(2) 0.3947(4) 0.82807(7) 0.0480(4) Uani 1 1 d . .
C12 C 0.3542(2) 0.1327(5) 0.79656(8) 0.0605(5) Uani 1 1 d . .
H12 H 0.2492 0.0480 0.7903 0.073 Uiso 1 1 calc R U
C11 C 0.4761(3) 0.1022(5) 0.76737(8) 0.0623(5) Uani 1 1 d . .
H11 H 0.4647 -0.0057 0.7385 0.075 Uiso 1 1 calc R U
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'
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
C12 S1 C9 91.75(10) . .
C6 N1 C7 125.25(16) . .
C6 N1 C8 117.42(15) . .
C7 N1 C8 117.31(15) . .
C5 C4 C3 119.60(17) . .
C5 C4 C7 120.36(16) . .
C3 C4 C7 120.04(15) . .
C1 C2 C3 119.66(18) . .
C1 C2 C6 120.34(16) . .
C3 C2 C6 119.99(16) . .
C3 C3 C2 119.70(19) 3_757 .
C3 C3 C4 119.54(19) 3_757 .
C2 C3 C4 120.75(17) . .
C4 C5 C1 120.72(16) . 3_757
O1 C7 N1 120.79(18) . .
O1 C7 C4 122.57(17) . .
N1 C7 C4 116.64(16) . .
O2 C6 N1 119.77(18) . .
O2 C6 C2 122.92(17) . .
N1 C6 C2 117.30(15) . .
C2 C1 C5 120.76(17) . 3_757
N1 C8 C9 112.21(15) . .
C9 C10 C11 112.72(18) . .
C10 C9 C8 127.20(17) . .
C10 C9 S1 110.92(15) . .
C8 C9 S1 121.88(14) . .
C11 C12 S1 112.04(16) . .
C12 C11 C10 112.56(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C12 1.700(2) .
S1 C9 1.7179(18) .
O1 C7 1.209(2) .
O2 C6 1.218(2) .
N1 C6 1.395(2) .
N1 C7 1.400(2) .
N1 C8 1.488(2) .
C4 C5 1.382(2) .
C4 C3 1.417(2) .
C4 C7 1.480(3) .
C2 C1 1.379(2) .
C2 C3 1.415(2) .
C2 C6 1.470(3) .
C3 C3 1.407(4) 3_757
C5 C1 1.395(3) 3_757
C1 C5 1.396(3) 3_757
C8 C9 1.498(3) .
C10 C9 1.355(3) .
C10 C11 1.414(3) .
C12 C11 1.345(3) .
