# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Fluorene_7-7-8-8-Tetracyanoquinodimethane
_audit_block_doi                 10.5517/ccdc.csd.cc2b039s
_database_code_depnum_ccdc_archive 'CCDC 2145054'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaoxu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2021-12-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 N4, C13 H10'
_chemical_formula_sum            'C25 H14 N4'
_chemical_formula_weight         370.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.0146(6)
_cell_length_b                   13.1035(6)
_cell_length_c                   6.7957(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.571(6)
_cell_angle_gamma                90
_cell_volume                     953.44(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1120
_cell_measurement_temperature    295.10(10)
_cell_measurement_theta_max      76.8480
_cell_measurement_theta_min      5.3020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       acicular
_exptl_crystal_F_000             384
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2504
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.023
_diffrn_reflns_theta_min         5.335
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00  89.00   0.50    0.50    --    0.00  57.00  90.00   52
  2  ω     59.00  84.00   0.50    0.50    --    0.00  57.00-120.00   50
  3  ω    -27.00  42.00   0.50    0.50    --    0.00  57.00-120.00  138
  4  ω      4.00  29.00   0.50    0.50    --    0.00  57.00  90.00   50
  5  ω     88.00 114.00   0.50    2.00    --  106.20  77.00 -60.00   52
  6  ω     47.00 139.00   0.50    2.00    --  106.20 -77.00   0.00  184
  7  ω    109.00 140.00   0.50    2.00    --  106.20 -82.00 120.00   62
  8  ω     17.00 101.00   0.50    2.00    --  106.20 -82.00 120.00  168
  9  ω     78.00 182.00   0.50    2.00    --  106.20  45.00  60.00  208
 10  ω     25.00  97.00   0.50    2.00    --  106.20 -30.00 -90.00  144
 11  ω    147.00 196.00   0.50    2.00    --  106.20  77.00 -60.00   98
 12  ω    161.00 187.00   0.50    2.00    --  106.20  82.00-150.00   52
 13  ω    101.00 130.00   0.50    2.00    --  106.20 -82.00  90.00   58
 14  ω    104.00 137.00   0.50    2.00    --  106.20  82.00-150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0414166000
_diffrn_orient_matrix_UB_12      0.0211799000
_diffrn_orient_matrix_UB_13      -0.2290326000
_diffrn_orient_matrix_UB_21      0.1372951000
_diffrn_orient_matrix_UB_22      -0.0032086000
_diffrn_orient_matrix_UB_23      -0.0151706000
_diffrn_orient_matrix_UB_31      -0.0115722000
_diffrn_orient_matrix_UB_32      -0.1155836000
_diffrn_orient_matrix_UB_33      -0.0416187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                844
_reflns_number_total             1051
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         1051
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.188
_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)+(0.0643P)²+0.1021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1274
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C16-C2 \\sim C16-C14 \\sim C5-C14 \\sim C5-C11 \\sim C2-C11
 with sigma of 0.01
 C11-C16 \\sim C16-C5
 with sigma of 0.01
3. Restrained planarity
 C10, C14, C16, C9, C5, C11, C7, C17, C12, C13, C15, C2, C3
 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C10, C12, C14, C16, C17, C9, C5, C11, C3, C13, C7, C15, C2
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
5. Others
 Fixed Sof: C10(0.25) H10(0.25) C12(0.25) H12(0.25) C14(0.25) C16(0.25)
 C17(0.25) H17(0.25) C9(0.25) H9(0.25) C5(0.25) H5A(0.25) H5B(0.25) C11(0.25)
 C3(0.25) H3(0.25) C13(0.25) H13(0.25) C7(0.25) H7(0.25) C15(0.25) H15(0.25)
 C2(0.25)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C12(H12), C17(H17), C9(H9), C3(H3), C13(H13), C7(H7),
 C15(H15)
6.c Fitted hexagon refined as free rotating group:
 C10(C12,C14,C16,C17,C9), C11(C3,C13,C7,C15,C2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C 0.13238(15) 0.500000 0.0507(2) 0.0492(4) Uani 1 2 d S T P . .
C4 C 0.26027(16) 0.500000 0.1005(2) 0.0532(4) Uani 1 2 d S T P . .
C6 C 0.06242(11) 0.40578(8) 0.02392(16) 0.0522(3) Uani 1 1 d . . . . .
H6 H 0.105034 0.343937 0.040255 0.063 Uiso 1 1 calc R U . . .
N1 N 0.38926(12) 0.66562(9) 0.1526(2) 0.0830(5) Uani 1 1 d . . . . .
C8 C 0.33160(12) 0.59240(9) 0.1290(2) 0.0606(4) Uani 1 1 d . . . . .
C10 C 0.8198(5) 1.0054(7) 0.6237(12) 0.0545(13) Uani 0.25 1 d G . P A -1
H10 H 0.905337 1.017615 0.657208 0.065 Uiso 0.25 1 calc R U P A -1
C12 C 0.7365(7) 1.0867(5) 0.5891(15) 0.0573(16) Uani 0.25 1 d G . P A -1
H12 H 0.766246 1.153350 0.599453 0.069 Uiso 0.25 1 calc R U P A -1
C14 C 0.6086(7) 1.0684(5) 0.5389(14) 0.0492(14) Uani 0.25 1 d DG . P A -1
C16 C 0.5641(5) 0.9687(6) 0.5234(12) 0.0477(14) Uani 0.25 1 d DG . P A -1
C17 C 0.6474(8) 0.8874(4) 0.5580(15) 0.0464(12) Uani 0.25 1 d G . P A -1
H17 H 0.617587 0.820741 0.547590 0.056 Uiso 0.25 1 calc R U P A -1
C9 C 0.7753(7) 0.9057(6) 0.6081(14) 0.0540(18) Uani 0.25 1 d G . P A -1
H9 H 0.831006 0.851308 0.631276 0.065 Uiso 0.25 1 calc R U P A -1
C5 C 0.5107(7) 1.1474(2) 0.4986(18) 0.0542(9) Uani 0.25 1 d D . P A -1
H5A H 0.516803 1.189386 0.383732 0.065 Uiso 0.25 1 calc R U P A -1
H5B H 0.515449 1.190743 0.615825 0.065 Uiso 0.25 1 calc R U P A -1
C11 C 0.3946(6) 1.0864(6) 0.4541(15) 0.0542(18) Uani 0.25 1 d DG . P A -1
C3 C 0.2686(7) 1.1117(4) 0.4037(15) 0.0540(13) Uani 0.25 1 d G . P A -1
H3 H 0.244273 1.179803 0.392702 0.065 Uiso 0.25 1 calc R U P A -1
C13 C 0.1788(5) 1.0351(5) 0.3698(13) 0.061(2) Uani 0.25 1 d G . P A -1
H13 H 0.094410 1.051929 0.336090 0.073 Uiso 0.25 1 calc R U P A -1
C7 C 0.2151(7) 0.9332(5) 0.3862(14) 0.0565(19) Uani 0.25 1 d G . P A -1
H7 H 0.154996 0.881955 0.363539 0.068 Uiso 0.25 1 calc R U P A -1
C15 C 0.3412(8) 0.9080(5) 0.4366(15) 0.059(2) Uani 0.25 1 d G . P A -1
H15 H 0.365444 0.839855 0.447601 0.071 Uiso 0.25 1 calc R U P A -1
C2 C 0.4309(6) 0.9846(7) 0.4705(13) 0.0539(16) Uani 0.25 1 d DG . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C4 1.369(2) . ?
C1 C6 1.4440(14) 6_565 ?
C1 C6 1.4440(14) . ?
C4 C8 1.4316(15) 6_565 ?
C4 C8 1.4315(15) . ?
C6 C6 1.337(2) 2 ?
C6 H6 0.9300 . ?
N1 C8 1.1409(16) . ?
C10 H10 0.9300 . ?
C10 C12 1.3900 . ?
C10 C9 1.3900 . ?
C12 H12 0.9300 . ?
C12 C14 1.3900 . ?
C14 C16 1.3900 . ?
C14 C5 1.474(5) . ?
C16 C17 1.3900 . ?
C16 C2 1.440(3) . ?
C17 H17 0.9300 . ?
C17 C9 1.3900 . ?
C9 H9 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C11 1.477(5) . ?
C11 C3 1.3900 . ?
C11 C2 1.3900 . ?
C3 H3 0.9300 . ?
C3 C13 1.3900 . ?
C13 H13 0.9300 . ?
C13 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C2 1.3900 . ?

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
C4 C1 C6 121.25(7) . . ?
C4 C1 C6 121.24(7) . 6_565 ?
C6 C1 C6 117.51(15) . 6_565 ?
C1 C4 C8 122.24(7) . . ?
C1 C4 C8 122.24(7) . 6_565 ?
C8 C4 C8 115.51(15) . 6_565 ?
C1 C6 H6 119.4 . . ?
C6 C6 C1 121.25(7) 2 . ?
C6 C6 H6 119.4 2 . ?
N1 C8 C4 179.43(16) . . ?
C12 C10 H10 120.0 . . ?
C12 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C12 H12 120.0 . . ?
C14 C12 C10 120.0 . . ?
C14 C12 H12 120.0 . . ?
C12 C14 C16 120.0 . . ?
C12 C14 C5 125.4(6) . . ?
C16 C14 C5 114.6(6) . . ?
C14 C16 C2 101.8(8) . . ?
C17 C16 C14 120.0 . . ?
C17 C16 C2 138.2(8) . . ?
C16 C17 H17 120.0 . . ?
C9 C17 C16 120.0 . . ?
C9 C17 H17 120.0 . . ?
C10 C9 H9 120.0 . . ?
C17 C9 C10 120.0 . . ?
C17 C9 H9 120.0 . . ?
C14 C5 H5A 111.2 . . ?
C14 C5 H5B 111.2 . . ?
C14 C5 C11 102.6(2) . . ?
H5A C5 H5B 109.2 . . ?
C11 C5 H5A 111.2 . . ?
C11 C5 H5B 111.2 . . ?
C3 C11 C5 133.5(5) . . ?
C3 C11 C2 120.0 . . ?
C2 C11 C5 106.5(5) . . ?
C11 C3 H3 120.0 . . ?
C13 C3 C11 120.0 . . ?
C13 C3 H3 120.0 . . ?
C3 C13 H13 120.0 . . ?
C3 C13 C7 120.0 . . ?
C7 C13 H13 120.0 . . ?
C13 C7 H7 120.0 . . ?
C13 C7 C15 120.0 . . ?
C15 C7 H7 120.0 . . ?
C7 C15 H15 120.0 . . ?
C2 C15 C7 120.0 . . ?
C2 C15 H15 120.0 . . ?
C11 C2 C16 114.5(8) . . ?
C15 C2 C16 125.5(8) . . ?
C15 C2 C11 120.0 . . ?

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
_geom_torsion_publ_flag
C4 C1 C6 C6 179.76(13) . . . 2 ?
C6 C1 C4 C8 -179.63(12) . . . . ?
C6 C1 C4 C8 179.63(12) 6_565 . . 6_565 ?
C6 C1 C4 C8 0.1(2) 6_565 . . . ?
C6 C1 C4 C8 -0.1(2) . . . 6_565 ?
C6 C1 C6 C6 0.0(2) 6_565 . . 2 ?
C10 C12 C14 C16 0.0 . . . . ?
C10 C12 C14 C5 -179.98(15) . . . . ?
C12 C10 C9 C17 0.0 . . . . ?
C12 C14 C16 C17 0.0 . . . . ?
C12 C14 C16 C2 179.99(8) . . . . ?
C12 C14 C5 C11 -179.98(10) . . . . ?
C14 C16 C17 C9 0.0 . . . . ?
C14 C16 C2 C11 0.01(11) . . . . ?
C14 C16 C2 C15 179.98(11) . . . . ?
C14 C5 C11 C3 -179.98(13) . . . . ?
C14 C5 C11 C2 0.0(2) . . . . ?
C16 C14 C5 C11 0.0(2) . . . . ?
C16 C17 C9 C10 0.0 . . . . ?
C17 C16 C2 C11 179.99(8) . . . . ?
C17 C16 C2 C15 -0.03(19) . . . . ?
C9 C10 C12 C14 0.0 . . . . ?
C5 C14 C16 C17 179.98(14) . . . . ?
C5 C14 C16 C2 -0.03(16) . . . . ?
C5 C11 C3 C13 180.0(3) . . . . ?
C5 C11 C2 C16 0.01(18) . . . . ?
C5 C11 C2 C15 -179.96(19) . . . . ?
C11 C3 C13 C7 0.0 . . . . ?
C3 C11 C2 C16 179.98(15) . . . . ?
C3 C11 C2 C15 0.0 . . . . ?
C3 C13 C7 C15 0.0 . . . . ?
C13 C7 C15 C2 0.0 . . . . ?
C7 C15 C2 C16 -179.97(16) . . . . ?
C7 C15 C2 C11 0.0 . . . . ?
C2 C16 C17 C9 -179.98(11) . . . . ?
C2 C11 C3 C13 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.842
_oxdiff_exptl_absorpt_empirical_full_min 0.611
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Dibenzofuran_7-7-8-8-Tetracyanoquinodimethane
_database_code_depnum_ccdc_archive 'CCDC 2145058'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaoxu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H4 N4, C12 H8 O'
_chemical_formula_sum            'C24 H12 N4 O'
_chemical_formula_weight         372.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7631(11)
_cell_length_b                   8.0049(16)
_cell_length_c                   9.0066(11)
_cell_angle_alpha                99.642(13)
_cell_angle_beta                 97.616(11)
_cell_angle_gamma                100.727(15)
_cell_volume                     465.52(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2389
_cell_measurement_temperature    293.39(10)
_cell_measurement_theta_max      78.3750
_cell_measurement_theta_min      6.6930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       acicular
_exptl_crystal_F_000             192
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4446
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.322
_diffrn_reflns_theta_min         5.054
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.39(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  88.00   0.50    0.50    --    0.00  57.00   0.00  106
  2  ω     28.00  55.00   0.50    0.50    --    0.00  57.00-120.00   54
  3  ω    -26.00  30.00   0.50    0.50    --    0.00  57.00   0.00  112
  4  ω     39.00  85.00   0.50    0.50    --    0.00  57.00  90.00   92
  5  ω    -24.00  21.00   0.50    0.50    --    0.00  57.00-120.00   90
  6  ω     20.00 134.00   0.50    4.60    --  106.20 -82.00 120.00  228
  7  ω    116.00 165.00   0.50    4.60    --  106.20  30.00 -60.00   98
  8  ω     48.00  91.00   0.50    4.60    --  106.20 -30.00 -30.00   86
  9  ω     41.00  67.00   0.50    4.60    --  106.20 -82.00 -90.00   52
 10  ω     80.00 142.00   0.50    4.60    --  106.20 -82.00-180.00  124
 11  ω     91.00 128.00   0.50    4.60    --  106.20 -82.00 -90.00   74
 12  ω     80.00 110.00   0.50    4.60    --  106.20  30.00-120.00   60
 13  ω    126.00 179.00   0.50    4.60    --  106.20  30.00-120.00  106
 14  ω     38.00  78.00   0.50    4.60    --  106.20 -82.00   0.00   80
 15  ω     76.00 112.00   0.50    4.60    --  106.20  30.00 -60.00   72
 16  ω    109.00 187.00   0.50    4.60    --  106.20  30.00 -30.00  156
 17  ω     78.00 103.00   0.50    4.60    --  106.20  30.00 -30.00   50
 18  ω     88.00 128.00   0.50    4.60    --  106.20 -82.00   0.00   80
 19  ω     76.00 189.00   0.50    4.60    --  106.20  30.00   0.00  226
 20  ω     97.00 137.00   0.50    4.60    --  106.20 -30.00 -30.00   80
 21  ω    145.00 190.00   0.50    4.60    --  106.20  30.00-150.00   90
 22  ω     78.00 104.00   0.50    4.60    --  106.20 -61.00   0.00   52
 23  ω     53.00 138.00   0.50    4.60    --  106.20 -82.00 -60.00  170
 24  ω     32.00 136.00   0.50    4.60    --  106.20 -61.00 120.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0709244000
_diffrn_orient_matrix_UB_12      0.1617170000
_diffrn_orient_matrix_UB_13      -0.0395719000
_diffrn_orient_matrix_UB_21      -0.1137459000
_diffrn_orient_matrix_UB_22      -0.1069701000
_diffrn_orient_matrix_UB_23      -0.1564278000
_diffrn_orient_matrix_UB_31      -0.1932935000
_diffrn_orient_matrix_UB_32      -0.0482294000
_diffrn_orient_matrix_UB_33      0.0703658000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1630
_reflns_number_total             1932
_reflns_odcompleteness_completeness 98.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1932
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.200
_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)+(0.0814P)²+0.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1672
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C3(0.5) H3(0.5) C2(0.5) H2(0.5) C1(0.5) C6(0.5) C5(0.5) H5(0.5)
 C4(0.5) H4(0.5) O1(0.5) C10(0.5) H10(0.5) C9(0.5) H9(0.5) C8(0.5) H8(0.5)
 C7(0.5) C12(0.5) C11(0.5) H11(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C3(H3), C2(H2), C5(H5), C4(H4), C10(H10), C9(H9), C8(H8),
 C11(H11)
3.b Fitted hexagon refined as free rotating group:
 C3(C2,C1,C6,C5,C4), C10(C9,C8,C7,C12,C11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C16 C 0.4466(2) 0.86801(17) 0.36691(14) 0.0411(3) Uani 1 1 d . . . . .
C18 C 0.5194(2) 0.95131(18) 0.64390(15) 0.0443(4) Uani 1 1 d . . . . .
H18 H 0.532529 0.921081 0.739473 0.053 Uiso 1 1 calc R . . . .
C15 C 0.3947(2) 0.73946(18) 0.23837(15) 0.0449(4) Uani 1 1 d . . . . .
C17 C 0.4691(2) 0.82649(18) 0.51741(15) 0.0446(4) Uani 1 1 d . . . . .
H17 H 0.448363 0.710861 0.526866 0.053 Uiso 1 1 calc R . . . .
N1 N 0.3470(3) 0.7970(2) -0.03561(16) 0.0717(5) Uani 1 1 d . . . . .
C13 C 0.3695(2) 0.77426(19) 0.08682(16) 0.0507(4) Uani 1 1 d . . . . .
N2 N 0.3301(3) 0.41537(19) 0.25144(19) 0.0760(5) Uani 1 1 d . . . . .
C14 C 0.3593(3) 0.5595(2) 0.24667(17) 0.0531(4) Uani 1 1 d . . . . .
C3 C -0.1312(7) -0.2788(8) 0.1622(3) 0.090(3) Uani 0.5 1 d . . P A -1
H3 H -0.163798 -0.338278 0.061255 0.108 Uiso 0.5 1 calc R . P A -1
C2 C -0.0882(6) -0.0986(8) 0.1949(5) 0.082(2) Uani 0.5 1 d G . P A -1
H2 H -0.092038 -0.037419 0.115747 0.098 Uiso 0.5 1 calc R . P A -1
C1 C -0.0394(6) -0.0097(4) 0.3458(7) 0.0607(14) Uani 0.5 1 d G . P A -1
C6 C -0.0336(5) -0.1011(6) 0.4640(3) 0.0482(9) Uani 0.5 1 d G . P A -1
C5 C -0.0766(4) -0.2814(6) 0.4314(4) 0.0606(12) Uani 0.5 1 d G . P A -1
H5 H -0.072689 -0.342530 0.510527 0.073 Uiso 0.5 1 calc R . P A -1
C4 C -0.1254(7) -0.3702(4) 0.2805(6) 0.0751(18) Uani 0.5 1 d G . P A -1
H4 H -0.154124 -0.490837 0.258648 0.090 Uiso 0.5 1 calc R . P A -1
O1 O 0.0051(4) 0.1634(4) 0.3939(3) 0.0723(8) Uani 0.5 1 d . . P A -1
C10 C 0.1293(7) 0.3428(3) 0.8083(6) 0.086(2) Uani 0.5 1 d . . P A -1
H10 H 0.165737 0.447352 0.878422 0.103 Uiso 0.5 1 calc R . P A -1
C9 C 0.1065(6) 0.1868(6) 0.8591(3) 0.0710(17) Uani 0.5 1 d G . P A -1
H9 H 0.127809 0.186938 0.963297 0.085 Uiso 0.5 1 calc R . P A -1
C8 C 0.0520(5) 0.0306(3) 0.7543(5) 0.0601(14) Uani 0.5 1 d G . P A -1
H8 H 0.036791 -0.073806 0.788291 0.072 Uiso 0.5 1 calc R . P A -1
C7 C 0.0202(5) 0.0304(4) 0.5986(4) 0.0469(12) Uani 0.5 1 d G . P A -1
C12 C 0.0429(5) 0.1864(7) 0.5477(3) 0.0591(13) Uani 0.5 1 d G . P A -1
C11 C 0.0974(6) 0.3426(4) 0.6526(6) 0.077(2) Uani 0.5 1 d G . P A -1
H11 H 0.112644 0.447019 0.618536 0.092 Uiso 0.5 1 calc R . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C16 C18 1.4435(19) 2_676 ?
C16 C15 1.372(2) . ?
C16 C17 1.4443(18) . ?
C18 C17 1.342(2) . ?
C15 C13 1.4329(19) . ?
C15 C14 1.432(2) . ?
N1 C13 1.143(2) . ?
N2 C14 1.143(2) . ?
C3 C2 1.3900 . ?
C3 C4 1.3900 . ?
C2 C1 1.3900 . ?
C1 C6 1.3900 . ?
C1 O1 1.345(4) . ?
C6 C5 1.3900 . ?
C6 C7 1.422(3) . ?
C5 C4 1.3900 . ?
O1 C12 1.349(4) . ?
C10 C9 1.3900 . ?
C10 C11 1.3900 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C12 1.3900 . ?
C12 C11 1.3900 . ?

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
C18 C16 C17 117.96(12) 2_676 . ?
C15 C16 C18 121.13(12) . 2_676 ?
C15 C16 C17 120.91(13) . . ?
C17 C18 C16 120.66(12) . 2_676 ?
C16 C15 C13 122.92(13) . . ?
C16 C15 C14 121.98(12) . . ?
C14 C15 C13 115.09(12) . . ?
C18 C17 C16 121.37(13) . . ?
N1 C13 C15 178.02(16) . . ?
N2 C14 C15 179.17(16) . . ?
C2 C3 C4 120.0 . . ?
C1 C2 C3 120.0 . . ?
C2 C1 C6 120.0 . . ?
O1 C1 C2 126.4(5) . . ?
O1 C1 C6 113.6(5) . . ?
C1 C6 C5 120.0 . . ?
C1 C6 C7 104.0(6) . . ?
C5 C6 C7 136.0(6) . . ?
C4 C5 C6 120.0 . . ?
C5 C4 C3 120.0 . . ?
C1 O1 C12 104.4(2) . . ?
C9 C10 C11 120.0 . . ?
C8 C9 C10 120.0 . . ?
C7 C8 C9 120.0 . . ?
C8 C7 C6 134.6(6) . . ?
C8 C7 C12 120.0 . . ?
C12 C7 C6 105.4(6) . . ?
O1 C12 C7 112.5(4) . . ?
O1 C12 C11 127.5(4) . . ?
C11 C12 C7 120.0 . . ?
C12 C11 C10 120.0 . . ?

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
_geom_torsion_publ_flag
C16 C18 C17 C16 -0.2(2) 2_676 . . . ?
C18 C16 C15 C13 -0.4(2) 2_676 . . . ?
C18 C16 C15 C14 -179.67(13) 2_676 . . . ?
C18 C16 C17 C18 0.2(2) 2_676 . . . ?
C15 C16 C17 C18 -179.84(13) . . . . ?
C17 C16 C15 C13 179.65(13) . . . . ?
C17 C16 C15 C14 0.4(2) . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C3 C2 C1 O1 -179.9(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C1 C6 C7 -179.9(3) . . . . ?
C2 C1 O1 C12 -179.5(3) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C1 C6 C7 C8 -180.0(2) . . . . ?
C1 C6 C7 C12 -0.5(3) . . . . ?
C1 O1 C12 C7 -0.9(3) . . . . ?
C1 O1 C12 C11 179.6(2) . . . . ?
C6 C1 O1 C12 0.6(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C6 C7 C12 O1 0.9(3) . . . . ?
C6 C7 C12 C11 -179.6(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C6 C7 C12 179.6(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
O1 C1 C6 C5 179.9(4) . . . . ?
O1 C1 C6 C7 0.0(3) . . . . ?
O1 C12 C11 C10 179.4(3) . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C8 C7 C6 179.4(3) . . . . ?
C9 C8 C7 C12 0.0 . . . . ?
C8 C7 C12 O1 -179.5(3) . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C7 C6 C5 C4 179.9(4) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.879
_oxdiff_exptl_absorpt_empirical_full_min 0.557
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Dibenzothiophene_7-7-8-8-Tetracyanoquinodimethane
_database_code_depnum_ccdc_archive 'CCDC 2145059'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaoxu'
;Tianjin University of Technology
China
;
_audit_update_record             
;
2022-01-28 deposited with the CCDC.	2022-10-31 downloaded from the CCDC.
;
_audit_creation_date             2022-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 S, C12 H4 N4'
_chemical_formula_sum            'C24 H12 N4 S'
_chemical_formula_weight         388.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.84060(10)
_cell_length_b                   8.9140(2)
_cell_length_c                   16.3304(3)
_cell_angle_alpha                100.164(2)
_cell_angle_beta                 98.574(2)
_cell_angle_gamma                98.373(2)
_cell_volume                     953.96(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5351
_cell_measurement_temperature    295.07(17)
_cell_measurement_theta_max      78.7130
_cell_measurement_theta_min      5.0720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       acicular
_exptl_crystal_F_000             400
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10867
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.460
_diffrn_reflns_theta_min         5.121
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.07(17)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  24.00   0.50    0.50    --    0.00 -37.00   0.00   98
  2  ω    -63.00 -36.00   0.50    0.50    --    0.00 -37.00   0.00   54
  3  ω    -89.00 -42.00   0.50    0.50    --    0.00 -77.00-120.00   94
  4  ω    -29.00  68.00   0.50    0.50    --    0.00  37.00   0.00  194
  5  ω    -11.00  29.00   0.50    0.50    --    0.00 -77.00-120.00   80
  6  ω     44.00  85.00   0.50    2.90    --  106.20 -77.00 -60.00   82
  7  ω    158.00 184.00   0.50    2.90    --  106.20  82.00-120.00   52
  8  ω     72.00 130.00   0.50    2.90    --  106.20 -61.00 -30.00  116
  9  ω    144.00 196.00   0.50    2.90    --  106.20  30.00-150.00  104
 10  ω     93.00 140.00   0.50    2.90    --  106.20 -30.00 -60.00   94
 11  ω     80.00 112.00   0.50    2.90    --  106.20 -82.00 -60.00   64
 12  ω     19.00 143.00   0.50    2.90    --  106.20 -82.00 150.00  248
 13  ω    103.00 129.00   0.50    2.90    --  106.20  82.00-120.00   52
 14  ω     74.00  99.00   0.50    2.90    --  106.20  30.00 -90.00   50
 15  ω     45.00  73.00   0.50    2.90    --  106.20 -30.00 -60.00   56
 16  ω    109.00 183.00   0.50    2.90    --  106.20  30.00 -90.00  148
 17  ω     17.00 141.00   0.50    2.90    --  106.20 -82.00-120.00  248
 18  ω     17.00  60.00   0.50    2.90    --  106.20 -82.00  30.00   86
 19  ω     92.00 128.00   0.50    2.90    --  106.20 -82.00  30.00   72
 20  ω     93.00 119.00   0.50    2.90    --  106.20  30.00-150.00   52
 21  ω     81.00 196.00   0.50    2.90    --  106.20  30.00 -30.00  230
 22  ω     29.00  64.00   0.50    2.90    --  106.20 -45.00   0.00   70
 23  ω     31.00  57.00   0.50    2.90    --  106.20 -61.00 -30.00   52
 24  ω     27.00 142.00   0.50    2.90    --  106.20 -82.00   0.00  230
 25  ω     96.00 122.00   0.50    2.90    --  106.20 -82.00 120.00   52
 26  ω     41.00 100.00   0.50    2.90    --  106.20 -45.00  60.00  118
 27  ω     23.00 118.00   0.50    2.90    --  106.20 -61.00 150.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080360000
_diffrn_orient_matrix_UB_12      0.1558088000
_diffrn_orient_matrix_UB_13      0.0599940000
_diffrn_orient_matrix_UB_21      -0.0861458000
_diffrn_orient_matrix_UB_22      0.0671523000
_diffrn_orient_matrix_UB_23      -0.0755252000
_diffrn_orient_matrix_UB_31      -0.2146069000
_diffrn_orient_matrix_UB_32      -0.0550955000
_diffrn_orient_matrix_UB_33      0.0137103000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3414
_reflns_number_total             4032
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.063
_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)+(0.1211P)²+0.3232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2023
_refine_ls_wR_factor_ref         0.2094
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C19(H19), C20(H20), C8(H8), C5(H5), C9(H9), C11(H11),
 C10(H10), C4(H4), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.02439(9) 0.13776(8) 0.15398(4) 0.0604(3) Uani 1 1 d . . . . .
C21 C 0.5835(3) 1.1322(2) 0.32324(13) 0.0379(4) Uani 1 1 d . . . . .
C16 C 0.4790(3) 0.8654(2) 0.19279(13) 0.0371(4) Uani 1 1 d . . . . .
C18 C 0.5059(3) 0.8520(2) 0.28047(13) 0.0390(4) Uani 1 1 d . . . . .
H18 H 0.488959 0.754619 0.294194 0.047 Uiso 1 1 calc R . . . .
C15 C 0.4269(3) 0.7357(2) 0.12906(14) 0.0412(5) Uani 1 1 d . . . . .
C22 C 0.6343(3) 1.2619(2) 0.38700(13) 0.0407(5) Uani 1 1 d . . . . .
C7 C 0.0528(3) 0.0389(3) 0.29607(14) 0.0411(5) Uani 1 1 d . . . . .
C17 C 0.5071(3) 1.0180(2) 0.17361(13) 0.0401(4) Uani 1 1 d . . . . .
H17 H 0.490816 1.028727 0.117490 0.048 Uiso 1 1 calc R . . . .
C19 C 0.5567(3) 1.1452(2) 0.23579(13) 0.0400(4) Uani 1 1 d . . . . .
H19 H 0.573743 1.242703 0.222120 0.048 Uiso 1 1 calc R . . . .
C20 C 0.5554(3) 0.9795(2) 0.34241(13) 0.0400(4) Uani 1 1 d . . . . .
H20 H 0.571807 0.968996 0.398565 0.048 Uiso 1 1 calc R . . . .
C6 C -0.0022(3) -0.0988(3) 0.23004(14) 0.0431(5) Uani 1 1 d . . . . .
N3 N 0.6882(4) 1.5405(2) 0.36116(16) 0.0687(7) Uani 1 1 d . . . . .
N2 N 0.3686(4) 0.4606(3) 0.15969(18) 0.0723(7) Uani 1 1 d . . . . .
C24 C 0.6627(4) 1.2527(3) 0.47447(15) 0.0488(5) Uani 1 1 d . . . . .
C23 C 0.6637(4) 1.4161(3) 0.37119(15) 0.0489(5) Uani 1 1 d . . . . .
C12 C 0.0726(3) 0.1749(3) 0.26346(16) 0.0479(5) Uani 1 1 d . . . . .
N4 N 0.6869(4) 1.2490(3) 0.54481(15) 0.0681(6) Uani 1 1 d . . . . .
C8 C 0.0865(3) 0.0500(3) 0.38386(15) 0.0480(5) Uani 1 1 d . . . . .
H8 H 0.074540 -0.038916 0.406492 0.058 Uiso 1 1 calc R . . . .
N1 N 0.3807(4) 0.7546(3) -0.02818(16) 0.0744(7) Uani 1 1 d . . . . .
C14 C 0.3944(4) 0.5826(3) 0.14600(15) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.4007(4) 0.7457(3) 0.04169(15) 0.0500(5) Uani 1 1 d . . . . .
C1 C -0.0248(3) -0.0608(3) 0.14941(15) 0.0520(6) Uani 1 1 d . . . . .
C5 C -0.0364(4) -0.2538(3) 0.23731(17) 0.0536(6) Uani 1 1 d . . . . .
H5 H -0.022890 -0.279958 0.290284 0.064 Uiso 1 1 calc R . . . .
C9 C 0.1377(4) 0.1943(3) 0.43631(17) 0.0597(6) Uani 1 1 d . . . . .
H9 H 0.160143 0.202267 0.494626 0.072 Uiso 1 1 calc R . . . .
C11 C 0.1260(4) 0.3212(3) 0.3184(2) 0.0606(7) Uani 1 1 d . . . . .
H11 H 0.140351 0.411444 0.297111 0.073 Uiso 1 1 calc R . . . .
C10 C 0.1561(4) 0.3274(3) 0.4033(2) 0.0662(7) Uani 1 1 d . . . . .
H10 H 0.189811 0.423372 0.440053 0.079 Uiso 1 1 calc R . . . .
C4 C -0.0903(4) -0.3673(4) 0.1651(2) 0.0700(8) Uani 1 1 d . . . . .
H4 H -0.112462 -0.470854 0.169281 0.084 Uiso 1 1 calc R . . . .
C2 C -0.0808(4) -0.1784(5) 0.07651(18) 0.0710(9) Uani 1 1 d . . . . .
H2 H -0.096199 -0.154376 0.023039 0.085 Uiso 1 1 calc R . . . .
C3 C -0.1119(4) -0.3282(4) 0.0856(2) 0.0787(10) Uani 1 1 d . . . . .
H3 H -0.148657 -0.406772 0.037591 0.094 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C12 1.732(3) . ?
S1 C1 1.739(3) . ?
C21 C22 1.375(3) . ?
C21 C19 1.440(3) . ?
C21 C20 1.443(3) . ?
C16 C18 1.444(3) . ?
C16 C15 1.376(3) . ?
C16 C17 1.442(3) . ?
C18 H18 0.9300 . ?
C18 C20 1.345(3) . ?
C15 C14 1.432(3) . ?
C15 C13 1.431(3) . ?
C22 C24 1.431(3) . ?
C22 C23 1.434(3) . ?
C7 C6 1.445(3) . ?
C7 C12 1.404(3) . ?
C7 C8 1.401(3) . ?
C17 H17 0.9300 . ?
C17 C19 1.346(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C6 C1 1.409(3) . ?
C6 C5 1.396(3) . ?
N3 C23 1.142(3) . ?
N2 C14 1.142(3) . ?
C24 N4 1.143(3) . ?
C12 C11 1.411(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
N1 C13 1.147(3) . ?
C1 C2 1.403(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.375(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.361(4) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.394(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(5) . ?
C3 H3 0.9300 . ?

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
C12 S1 C1 91.38(11) . . ?
C22 C21 C19 120.97(18) . . ?
C22 C21 C20 120.73(19) . . ?
C19 C21 C20 118.30(18) . . ?
C15 C16 C18 120.82(18) . . ?
C15 C16 C17 120.75(19) . . ?
C17 C16 C18 118.43(18) . . ?
C16 C18 H18 119.8 . . ?
C20 C18 C16 120.46(18) . . ?
C20 C18 H18 119.8 . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 C13 121.93(19) . . ?
C13 C15 C14 115.96(19) . . ?
C21 C22 C24 122.25(19) . . ?
C21 C22 C23 122.82(19) . . ?
C24 C22 C23 114.93(19) . . ?
C12 C7 C6 112.2(2) . . ?
C8 C7 C6 128.5(2) . . ?
C8 C7 C12 119.3(2) . . ?
C16 C17 H17 119.5 . . ?
C19 C17 C16 120.91(19) . . ?
C19 C17 H17 119.5 . . ?
C21 C19 H19 119.6 . . ?
C17 C19 C21 120.78(18) . . ?
C17 C19 H19 119.6 . . ?
C21 C20 H20 119.4 . . ?
C18 C20 C21 121.13(19) . . ?
C18 C20 H20 119.4 . . ?
C1 C6 C7 111.1(2) . . ?
C5 C6 C7 129.0(2) . . ?
C5 C6 C1 119.8(2) . . ?
N4 C24 C22 178.4(2) . . ?
N3 C23 C22 178.0(2) . . ?
C7 C12 S1 112.54(18) . . ?
C7 C12 C11 120.4(2) . . ?
C11 C12 S1 127.0(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
N2 C14 C15 179.9(3) . . ?
N1 C13 C15 179.5(3) . . ?
C6 C1 S1 112.73(18) . . ?
C2 C1 S1 127.1(2) . . ?
C2 C1 C6 120.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 H5 120.4 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.6(2) . . ?
C10 C11 H11 120.7 . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C5 C4 H4 119.7 . . ?
C5 C4 C3 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C4 C3 H3 119.1 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?

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
_geom_torsion_publ_flag
S1 C12 C11 C10 179.3(2) . . . . ?
S1 C1 C2 C3 179.6(2) . . . . ?
C16 C18 C20 C21 -0.2(3) . . . . ?
C16 C17 C19 C21 0.2(3) . . . . ?
C18 C16 C15 C14 0.9(3) . . . . ?
C18 C16 C15 C13 -179.53(19) . . . . ?
C18 C16 C17 C19 -0.2(3) . . . . ?
C15 C16 C18 C20 -179.5(2) . . . . ?
C15 C16 C17 C19 179.5(2) . . . . ?
C22 C21 C19 C17 180.0(2) . . . . ?
C22 C21 C20 C18 -179.9(2) . . . . ?
C7 C6 C1 S1 1.1(2) . . . . ?
C7 C6 C1 C2 -179.1(2) . . . . ?
C7 C6 C5 C4 179.2(2) . . . . ?
C7 C12 C11 C10 -0.5(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C17 C16 C18 C20 0.2(3) . . . . ?
C17 C16 C15 C14 -178.9(2) . . . . ?
C17 C16 C15 C13 0.7(3) . . . . ?
C19 C21 C22 C24 -179.8(2) . . . . ?
C19 C21 C22 C23 -0.1(3) . . . . ?
C19 C21 C20 C18 0.2(3) . . . . ?
C20 C21 C22 C24 0.4(3) . . . . ?
C20 C21 C22 C23 -180.0(2) . . . . ?
C20 C21 C19 C17 -0.2(3) . . . . ?
C6 C7 C12 S1 0.3(2) . . . . ?
C6 C7 C12 C11 -179.9(2) . . . . ?
C6 C7 C8 C9 -179.8(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C5 C4 C3 -0.4(4) . . . . ?
C12 S1 C1 C6 -0.83(18) . . . . ?
C12 S1 C1 C2 179.5(2) . . . . ?
C12 C7 C6 C1 -0.9(3) . . . . ?
C12 C7 C6 C5 -179.6(2) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
C12 C11 C10 C9 0.7(4) . . . . ?
C8 C7 C6 C1 179.2(2) . . . . ?
C8 C7 C6 C5 0.5(4) . . . . ?
C8 C7 C12 S1 -179.81(16) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C1 S1 C12 C7 0.31(18) . . . . ?
C1 S1 C12 C11 -179.5(2) . . . . ?
C1 C6 C5 C4 0.5(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C5 C6 C1 S1 179.99(17) . . . . ?
C5 C6 C1 C2 -0.3(4) . . . . ?
C5 C4 C3 C2 0.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.776
_oxdiff_exptl_absorpt_empirical_full_min 0.368
