# 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_SPA713
_database_code_depnum_ccdc_archive 'CCDC 2128858'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   16.071(3)
_cell_length_b                   8.3680(17)
_cell_length_c                   23.949(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.49(3)
_cell_angle_gamma                90
_cell_volume                     3144.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    50712
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14235
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.544
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3938
_reflns_number_gt                3462
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1063P)²+0.8768P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1804
_refine_ls_wR_factor_gt          0.1753
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.60378(8) 0.53331(15) 0.41852(5) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.37353(7) 0.57274(13) 0.25561(5) 0.0409(3) Uani 1 1 d . . . . .
C1 C 0.50657(7) 0.92111(13) 0.37277(4) 0.0294(3) Uani 1 1 d . . . . .
C2 C 0.59404(7) 0.95580(13) 0.37693(5) 0.0299(3) Uani 1 1 d . . . . .
C3 C 0.64543(8) 0.87712(15) 0.34369(5) 0.0363(3) Uani 1 1 d . . . . .
H3 H 0.620448 0.800968 0.316307 0.044 Uiso 1 1 calc R U . . .
C4 C 0.73031(9) 0.91037(17) 0.35093(6) 0.0433(3) Uani 1 1 d . . . . .
H4 H 0.763059 0.855428 0.328999 0.052 Uiso 1 1 calc R U . . .
C5 C 0.76953(9) 1.02648(19) 0.39101(6) 0.0453(3) Uani 1 1 d . . . . .
H5 H 0.828287 1.046321 0.396267 0.054 Uiso 1 1 calc R U . . .
C6 C 0.72255(8) 1.10897(18) 0.42176(5) 0.0404(3) Uani 1 1 d . . . . .
H6 H 0.748969 1.187931 0.447500 0.048 Uiso 1 1 calc R U . . .
C7 C 0.63342(8) 1.07849(14) 0.41593(5) 0.0318(3) Uani 1 1 d . . . . .
C8 C 0.58506(8) 1.16324(15) 0.44732(5) 0.0335(3) Uani 1 1 d . . . . .
H8 H 0.611499 1.243069 0.472654 0.040 Uiso 1 1 calc R U . . .
C9 C 0.49853(8) 1.13359(14) 0.44241(4) 0.0318(3) Uani 1 1 d . . . . .
C10 C 0.44888(9) 1.22275(16) 0.47420(5) 0.0400(3) Uani 1 1 d . . . . .
H10 H 0.474821 1.305012 0.498588 0.048 Uiso 1 1 calc R U . . .
C11 C 0.36509(10) 1.19113(19) 0.46992(6) 0.0462(3) Uani 1 1 d . . . . .
H11 H 0.333243 1.252044 0.490840 0.055 Uiso 1 1 calc R U . . .
C12 C 0.32558(9) 1.06629(19) 0.43392(6) 0.0455(3) Uani 1 1 d . . . . .
H12 H 0.267552 1.044094 0.431431 0.055 Uiso 1 1 calc R U . . .
C13 C 0.37044(8) 0.97784(17) 0.40283(5) 0.0375(3) Uani 1 1 d . . . . .
H13 H 0.342990 0.894634 0.379557 0.045 Uiso 1 1 calc R U . . .
C14 C 0.45850(7) 1.00917(14) 0.40492(4) 0.0301(3) Uani 1 1 d . . . . .
C15 C 0.46288(7) 0.79403(14) 0.33480(5) 0.0324(3) Uani 1 1 d . . . . .
H15 H 0.417316 0.825915 0.305271 0.039 Uiso 1 1 calc R U . . .
C16 C 0.48158(7) 0.63715(14) 0.33809(4) 0.0292(3) Uani 1 1 d . . . . .
C17 C 0.55012(8) 0.58053(14) 0.38281(5) 0.0326(3) Uani 1 1 d . . . . .
C18 C 0.43269(7) 0.51518(14) 0.29923(4) 0.0296(3) Uani 1 1 d . . . . .
C19 C 0.44721(8) 0.35320(15) 0.30847(5) 0.0362(3) Uani 1 1 d . . . . .
H19 H 0.489217 0.316819 0.339494 0.043 Uiso 1 1 calc R U . . .
C20 C 0.39831(10) 0.24553(16) 0.27087(6) 0.0450(3) Uani 1 1 d . . . . .
H20 H 0.406539 0.134886 0.276174 0.054 Uiso 1 1 calc R U . . .
C21 C 0.33770(10) 0.30333(18) 0.22581(6) 0.0478(4) Uani 1 1 d . . . . .
H21 H 0.303858 0.233455 0.199617 0.057 Uiso 1 1 calc R U . . .
C22 C 0.32798(10) 0.46699(19) 0.22013(6) 0.0486(4) Uani 1 1 d . . . . .
H22 H 0.286584 0.506124 0.189265 0.058 Uiso 1 1 calc R U . . .


_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
N1 C17 1.1456(17) . ?
N2 C22 1.3311(17) . ?
N2 C18 1.3410(15) . ?
C1 C14 1.4106(17) . ?
C1 C2 1.4177(17) . ?
C1 C15 1.4747(16) . ?
C2 C3 1.4259(17) . ?
C2 C7 1.4393(16) . ?
C3 C4 1.3660(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.353(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.4319(17) . ?
C6 H6 0.9400 . ?
C7 C8 1.3873(18) . ?
C8 C9 1.3924(17) . ?
C8 H8 0.9400 . ?
C9 C10 1.4268(17) . ?
C9 C14 1.4332(16) . ?
C10 C11 1.354(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.415(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.362(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4296(17) . ?
C13 H13 0.9400 . ?
C15 C16 1.3452(17) . ?
C15 H15 0.9400 . ?
C16 C17 1.4405(16) . ?
C16 C18 1.4862(15) . ?
C18 C19 1.3850(17) . ?
C19 C20 1.3908(17) . ?
C19 H19 0.9400 . ?
C20 C21 1.376(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?

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
C22 N2 C18 117.26(12) . . ?
C14 C1 C2 120.43(10) . . ?
C14 C1 C15 117.99(11) . . ?
C2 C1 C15 121.58(11) . . ?
C1 C2 C3 123.47(11) . . ?
C1 C2 C7 118.80(11) . . ?
C3 C2 C7 117.72(11) . . ?
C4 C3 C2 121.21(12) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.81(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.05(12) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 121.36(13) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.46(11) . . ?
C8 C7 C2 119.81(11) . . ?
C6 C7 C2 118.72(11) . . ?
C7 C8 C9 121.97(11) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C10 121.69(11) . . ?
C8 C9 C14 119.15(11) . . ?
C10 C9 C14 119.15(11) . . ?
C11 C10 C9 121.27(13) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.89(13) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.91(13) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.22(12) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C1 C14 C13 122.68(11) . . ?
C1 C14 C9 119.79(11) . . ?
C13 C14 C9 117.52(11) . . ?
C16 C15 C1 126.66(10) . . ?
C16 C15 H15 116.7 . . ?
C1 C15 H15 116.7 . . ?
C15 C16 C17 119.32(10) . . ?
C15 C16 C18 123.53(10) . . ?
C17 C16 C18 117.09(10) . . ?
N1 C17 C16 178.82(14) . . ?
N2 C18 C19 122.86(11) . . ?
N2 C18 C16 115.53(11) . . ?
C19 C18 C16 121.61(10) . . ?
C18 C19 C20 118.59(12) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 119.03(13) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 118.13(12) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
N2 C22 C21 124.14(13) . . ?
N2 C22 H22 117.9 . . ?
C21 C22 H22 117.9 . . ?

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
C14 C1 C2 C3 -176.84(10) . . . . ?
C15 C1 C2 C3 2.67(17) . . . . ?
C14 C1 C2 C7 2.11(16) . . . . ?
C15 C1 C2 C7 -178.38(10) . . . . ?
C1 C2 C3 C4 -177.35(11) . . . . ?
C7 C2 C3 C4 3.69(18) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C4 C5 C6 C7 1.8(2) . . . . ?
C5 C6 C7 C8 -179.82(12) . . . . ?
C5 C6 C7 C2 0.81(18) . . . . ?
C1 C2 C7 C8 -1.85(16) . . . . ?
C3 C2 C7 C8 177.16(10) . . . . ?
C1 C2 C7 C6 177.53(10) . . . . ?
C3 C2 C7 C6 -3.46(16) . . . . ?
C6 C7 C8 C9 -179.37(11) . . . . ?
C2 C7 C8 C9 -0.01(17) . . . . ?
C7 C8 C9 C10 -179.08(11) . . . . ?
C7 C8 C9 C14 1.59(17) . . . . ?
C8 C9 C10 C11 -178.80(12) . . . . ?
C14 C9 C10 C11 0.52(19) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C2 C1 C14 C13 -179.24(10) . . . . ?
C15 C1 C14 C13 1.24(17) . . . . ?
C2 C1 C14 C9 -0.55(16) . . . . ?
C15 C1 C14 C9 179.92(9) . . . . ?
C12 C13 C14 C1 -179.25(11) . . . . ?
C12 C13 C14 C9 2.04(18) . . . . ?
C8 C9 C14 C1 -1.31(16) . . . . ?
C10 C9 C14 C1 179.35(10) . . . . ?
C8 C9 C14 C13 177.44(10) . . . . ?
C10 C9 C14 C13 -1.90(16) . . . . ?
C14 C1 C15 C16 -118.62(14) . . . . ?
C2 C1 C15 C16 61.86(17) . . . . ?
C1 C15 C16 C17 0.70(19) . . . . ?
C1 C15 C16 C18 177.98(10) . . . . ?
C22 N2 C18 C19 -0.34(19) . . . . ?
C22 N2 C18 C16 -179.49(12) . . . . ?
C15 C16 C18 N2 7.36(17) . . . . ?
C17 C16 C18 N2 -175.31(11) . . . . ?
C15 C16 C18 C19 -171.80(12) . . . . ?
C17 C16 C18 C19 5.54(17) . . . . ?
N2 C18 C19 C20 0.00(19) . . . . ?
C16 C18 C19 C20 179.10(11) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C18 N2 C22 C21 0.4(2) . . . . ?
C20 C21 C22 N2 -0.1(3) . . . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_SPA669
_database_code_depnum_ccdc_archive 'CCDC 2128859'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.306(2)
_cell_length_b                   18.839(4)
_cell_length_c                   8.9120(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.03(3)
_cell_angle_gamma                90
_cell_volume                     1603.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    50459
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.069
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14892
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.890
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3987
_reflns_number_gt                3472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+0.2360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3987
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1473
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.57431(12) 0.24002(6) 0.93421(15) 0.0419(3) Uani 1 1 d . . . . .
N2 N 0.90449(12) 0.32985(6) 0.71078(17) 0.0458(3) Uani 1 1 d . . . . .
C1 C 0.64716(12) 0.28201(6) 0.87288(16) 0.0344(3) Uani 1 1 d . . . . .
H1 H 0.740936 0.270116 0.893870 0.041 Uiso 1 1 calc R U . . .
C2 C 0.44168(13) 0.25719(8) 0.90228(17) 0.0409(3) Uani 1 1 d . . . . .
H2 H 0.389194 0.228387 0.944703 0.049 Uiso 1 1 calc R U . . .
C3 C 0.37714(13) 0.31505(8) 0.81019(19) 0.0460(4) Uani 1 1 d . . . . .
H3 H 0.282709 0.325113 0.789866 0.055 Uiso 1 1 calc R U . . .
C4 C 0.45346(13) 0.35808(7) 0.74816(17) 0.0396(3) Uani 1 1 d . . . . .
H4 H 0.411389 0.397839 0.684865 0.048 Uiso 1 1 calc R U . . .
C5 C 0.59238(11) 0.34219(6) 0.77995(12) 0.0257(2) Uani 1 1 d . . . . .
C6 C 0.67826(10) 0.38697(6) 0.71564(12) 0.0253(2) Uani 1 1 d . . . . .
C7 C 0.80355(11) 0.35484(6) 0.71011(14) 0.0307(3) Uani 1 1 d . . . . .
C8 C 0.64870(11) 0.45475(6) 0.66811(13) 0.0287(2) Uani 1 1 d . . . . .
H8 H 0.569408 0.474944 0.679285 0.034 Uiso 1 1 calc R U . . .
C9 C 0.72958(11) 0.50045(6) 0.59981(13) 0.0263(2) Uani 1 1 d . . . . .
C10 C 0.74590(11) 0.48239(6) 0.45375(13) 0.0270(2) Uani 1 1 d . . . . .
C11 C 0.67892(13) 0.42238(7) 0.35788(15) 0.0363(3) Uani 1 1 d . . . . .
H11 H 0.622792 0.392527 0.392884 0.044 Uiso 1 1 calc R U . . .
C12 C 0.69550(17) 0.40793(8) 0.21612(16) 0.0463(3) Uani 1 1 d . . . . .
H12 H 0.649995 0.368411 0.154330 0.056 Uiso 1 1 calc R U . . .
C13 C 0.78037(16) 0.45163(8) 0.16051(16) 0.0456(3) Uani 1 1 d . . . . .
H13 H 0.791895 0.440432 0.063467 0.055 Uiso 1 1 calc R U . . .
C14 C 0.84475(13) 0.50933(7) 0.24667(15) 0.0364(3) Uani 1 1 d . . . . .
H14 H 0.900813 0.537888 0.208800 0.044 Uiso 1 1 calc R U . . .
C15 C 0.82873(11) 0.52751(6) 0.39457(13) 0.0278(2) Uani 1 1 d . . . . .
C16 C 0.89086(11) 0.58809(6) 0.48070(14) 0.0295(2) Uani 1 1 d . . . . .
H16 H 0.947835 0.616249 0.443360 0.035 Uiso 1 1 calc R U . . .
C17 C 0.87083(11) 0.60811(6) 0.62096(14) 0.0287(2) Uani 1 1 d . . . . .
C18 C 0.93392(13) 0.67077(7) 0.70795(16) 0.0366(3) Uani 1 1 d . . . . .
H18 H 0.988686 0.699694 0.668936 0.044 Uiso 1 1 calc R U . . .
C19 C 0.91601(15) 0.68915(8) 0.84587(18) 0.0444(3) Uani 1 1 d . . . . .
H19 H 0.958186 0.730584 0.901736 0.053 Uiso 1 1 calc R U . . .
C20 C 0.83366(17) 0.64594(8) 0.90611(17) 0.0465(3) Uani 1 1 d . . . . .
H20 H 0.821501 0.659213 1.001672 0.056 Uiso 1 1 calc R U . . .
C21 C 0.77207(14) 0.58566(7) 0.82780(16) 0.0379(3) Uani 1 1 d . . . . .
H21 H 0.718168 0.557820 0.870164 0.046 Uiso 1 1 calc R U . . .
C22 C 0.78804(11) 0.56397(6) 0.68200(13) 0.0280(2) Uani 1 1 d . . . . .


_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
N1 C2 1.3275(17) . ?
N1 C1 1.3402(15) . ?
N2 C7 1.1399(16) . ?
C1 C5 1.3926(16) . ?
C1 H1 0.9400 . ?
C2 C3 1.3764(19) . ?
C2 H2 0.9400 . ?
C3 C4 1.3812(17) . ?
C3 H3 0.9400 . ?
C4 C5 1.3839(16) . ?
C4 H4 0.9400 . ?
C5 C6 1.4846(14) . ?
C6 C8 1.3438(16) . ?
C6 C7 1.4435(15) . ?
C8 C9 1.4790(14) . ?
C8 H8 0.9400 . ?
C9 C22 1.4143(16) . ?
C9 C10 1.4152(15) . ?
C10 C11 1.4289(16) . ?
C10 C15 1.4379(15) . ?
C11 C12 1.3644(18) . ?
C11 H11 0.9400 . ?
C12 C13 1.419(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.352(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.4301(16) . ?
C14 H14 0.9400 . ?
C15 C16 1.3902(16) . ?
C16 C17 1.3933(16) . ?
C16 H16 0.9400 . ?
C17 C18 1.4281(16) . ?
C17 C22 1.4365(15) . ?
C18 C19 1.3546(19) . ?
C18 H18 0.9400 . ?
C19 C20 1.419(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.3591(19) . ?
C20 H20 0.9400 . ?
C21 C22 1.4293(16) . ?
C21 H21 0.9400 . ?

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
C2 N1 C1 117.26(11) . . ?
N1 C1 C5 123.99(11) . . ?
N1 C1 H1 118.0 . . ?
C5 C1 H1 118.0 . . ?
N1 C2 C3 123.32(11) . . ?
N1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C2 C3 C4 118.88(11) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 119.46(11) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C1 117.08(10) . . ?
C4 C5 C6 121.26(10) . . ?
C1 C5 C6 121.66(9) . . ?
C8 C6 C7 119.18(9) . . ?
C8 C6 C5 124.34(9) . . ?
C7 C6 C5 116.45(9) . . ?
N2 C7 C6 177.87(14) . . ?
C6 C8 C9 125.93(10) . . ?
C6 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
C22 C9 C10 120.35(10) . . ?
C22 C9 C8 118.41(10) . . ?
C10 C9 C8 121.22(10) . . ?
C9 C10 C11 122.87(10) . . ?
C9 C10 C15 119.14(10) . . ?
C11 C10 C15 117.94(10) . . ?
C12 C11 C10 120.75(12) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 121.02(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 120.22(12) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.94(12) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 121.13(11) . . ?
C16 C15 C10 119.78(10) . . ?
C14 C15 C10 119.09(11) . . ?
C15 C16 C17 121.67(10) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 121.35(10) . . ?
C16 C17 C22 119.48(10) . . ?
C18 C17 C22 119.15(10) . . ?
C19 C18 C17 120.97(12) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.07(12) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 121.04(12) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.99(12) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C9 C22 C21 122.74(10) . . ?
C9 C22 C17 119.45(10) . . ?
C21 C22 C17 117.78(11) . . ?

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
C2 N1 C1 C5 0.6(2) . . . . ?
C1 N1 C2 C3 0.2(2) . . . . ?
N1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C1 0.8(2) . . . . ?
C3 C4 C5 C6 179.97(13) . . . . ?
N1 C1 C5 C4 -1.07(19) . . . . ?
N1 C1 C5 C6 179.74(12) . . . . ?
C4 C5 C6 C8 21.32(18) . . . . ?
C1 C5 C6 C8 -159.52(12) . . . . ?
C4 C5 C6 C7 -160.73(12) . . . . ?
C1 C5 C6 C7 18.43(16) . . . . ?
C7 C6 C8 C9 3.70(18) . . . . ?
C5 C6 C8 C9 -178.41(10) . . . . ?
C6 C8 C9 C22 -120.30(13) . . . . ?
C6 C8 C9 C10 61.18(16) . . . . ?
C22 C9 C10 C11 -174.24(10) . . . . ?
C8 C9 C10 C11 4.26(16) . . . . ?
C22 C9 C10 C15 3.22(15) . . . . ?
C8 C9 C10 C15 -178.29(9) . . . . ?
C9 C10 C11 C12 178.63(12) . . . . ?
C15 C10 C11 C12 1.15(18) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C14 -1.1(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 -177.81(11) . . . . ?
C13 C14 C15 C10 1.71(18) . . . . ?
C9 C10 C15 C16 -0.26(15) . . . . ?
C11 C10 C15 C16 177.32(10) . . . . ?
C9 C10 C15 C14 -179.79(10) . . . . ?
C11 C10 C15 C14 -2.21(15) . . . . ?
C14 C15 C16 C17 177.03(10) . . . . ?
C10 C15 C16 C17 -2.48(16) . . . . ?
C15 C16 C17 C18 -179.40(10) . . . . ?
C15 C16 C17 C22 2.24(16) . . . . ?
C16 C17 C18 C19 -178.77(12) . . . . ?
C22 C17 C18 C19 -0.39(18) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C10 C9 C22 C21 178.51(10) . . . . ?
C8 C9 C22 C21 -0.02(16) . . . . ?
C10 C9 C22 C17 -3.47(16) . . . . ?
C8 C9 C22 C17 178.00(9) . . . . ?
C20 C21 C22 C9 177.85(12) . . . . ?
C20 C21 C22 C17 -0.21(19) . . . . ?
C16 C17 C22 C9 0.76(16) . . . . ?
C18 C17 C22 C9 -177.65(10) . . . . ?
C16 C17 C22 C21 178.88(10) . . . . ?
C18 C17 C22 C21 0.47(16) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_SPA714
_database_code_depnum_ccdc_archive 'CCDC 2128861'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 N2, C7 H7 O3 S'
_chemical_formula_sum            'C29 H22 N2 O3 S'
_chemical_formula_weight         478.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1022 0.0976 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7390(14)
_cell_length_b                   11.596(2)
_cell_length_c                   15.268(3)
_cell_angle_alpha                103.81(3)
_cell_angle_beta                 92.11(3)
_cell_angle_gamma                95.34(3)
_cell_volume                     1151.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    37099
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.039
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10956
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.220
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             5499
_reflns_number_gt                4337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0846P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.2312(2) 0.49086(14) 0.44518(10) 0.0391(3) Uani 1 1 d . . . . .
N2 N 0.67748(19) 0.20706(11) 0.46157(8) 0.0250(3) Uani 1 1 d . . . . .
H2 H 0.763232 0.211730 0.421008 0.030 Uiso 1 1 calc R U . . .
C1 C 0.5536(2) 0.41476(13) 0.25871(10) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.3757(2) 0.39585(13) 0.20316(10) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.2172(2) 0.30561(14) 0.20512(11) 0.0316(3) Uani 1 1 d . . . . .
H3 H 0.229967 0.255637 0.244812 0.038 Uiso 1 1 calc R U . . .
C4 C 0.0485(3) 0.29112(16) 0.15038(12) 0.0366(4) Uani 1 1 d . . . . .
H4 H -0.055188 0.232545 0.153810 0.044 Uiso 1 1 calc R U . . .
C5 C 0.0266(3) 0.36288(17) 0.08832(14) 0.0425(4) Uani 1 1 d . . . . .
H5 H -0.090875 0.351408 0.050758 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1733(3) 0.44757(17) 0.08283(13) 0.0404(4) Uani 1 1 d . . . . .
H6 H 0.157526 0.493796 0.040656 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3527(2) 0.46858(14) 0.13995(11) 0.0311(3) Uani 1 1 d . . . . .
C8 C 0.5032(3) 0.55690(15) 0.13500(12) 0.0347(4) Uani 1 1 d . . . . .
H8 H 0.486418 0.603752 0.093338 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6789(2) 0.57769(14) 0.19043(11) 0.0305(3) Uani 1 1 d . . . . .
C10 C 0.8319(3) 0.66994(15) 0.18642(13) 0.0377(4) Uani 1 1 d . . . . .
H10 H 0.815110 0.717853 0.145515 0.045 Uiso 1 1 calc R U . . .
C11 C 1.0007(3) 0.68903(16) 0.24083(14) 0.0417(4) Uani 1 1 d . . . . .
H11 H 1.100024 0.750192 0.237699 0.050 Uiso 1 1 calc R U . . .
C12 C 1.0283(3) 0.61728(16) 0.30248(13) 0.0396(4) Uani 1 1 d . . . . .
H12 H 1.146946 0.630836 0.339429 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8862(2) 0.52911(15) 0.30921(12) 0.0331(3) Uani 1 1 d . . . . .
H13 H 0.907088 0.483394 0.351300 0.040 Uiso 1 1 calc R U . . .
C14 C 0.7056(2) 0.50512(13) 0.25310(10) 0.0282(3) Uani 1 1 d . . . . .
C15 C 0.5883(2) 0.33841(14) 0.32205(10) 0.0283(3) Uani 1 1 d . . . . .
H15 H 0.689220 0.287046 0.309884 0.034 Uiso 1 1 calc R U . . .
C16 C 0.4854(2) 0.33785(13) 0.39541(10) 0.0243(3) Uani 1 1 d . . . . .
C17 C 0.3387(2) 0.42117(14) 0.41959(10) 0.0284(3) Uani 1 1 d . . . . .
C18 C 0.5125(2) 0.26457(13) 0.46129(10) 0.0240(3) Uani 1 1 d . . . . .
C19 C 0.3754(2) 0.25491(15) 0.52535(11) 0.0310(3) Uani 1 1 d . . . . .
H19 H 0.258480 0.293433 0.526438 0.037 Uiso 1 1 calc R U . . .
C20 C 0.4101(3) 0.18864(15) 0.58780(12) 0.0348(4) Uani 1 1 d . . . . .
H20 H 0.316577 0.181687 0.630906 0.042 Uiso 1 1 calc R U . . .
C21 C 0.5832(3) 0.13275(15) 0.58643(11) 0.0326(3) Uani 1 1 d . . . . .
H21 H 0.609587 0.088685 0.629062 0.039 Uiso 1 1 calc R U . . .
C22 C 0.7153(2) 0.14277(14) 0.52182(11) 0.0297(3) Uani 1 1 d . . . . .
H22 H 0.832778 0.104615 0.519585 0.036 Uiso 1 1 calc R U . . .
S1 S 1.03625(5) 0.06176(3) 0.32214(3) 0.02704(12) Uani 1 1 d . . . . .
O1 O 0.98298(17) 0.18496(10) 0.35369(8) 0.0333(3) Uani 1 1 d . . . . .
O2 O 0.98269(17) -0.01018(11) 0.38518(8) 0.0352(3) Uani 1 1 d . . . . .
O3 O 1.24022(16) 0.05868(11) 0.29627(8) 0.0358(3) Uani 1 1 d . . . . .
C23 C 0.8802(2) -0.00100(13) 0.22276(10) 0.0268(3) Uani 1 1 d . . . . .
C24 C 0.6766(2) -0.01907(16) 0.23055(12) 0.0351(4) Uani 1 1 d . . . . .
H24 H 0.623612 0.004937 0.287366 0.042 Uiso 1 1 calc R U . . .
C25 C 0.5501(3) -0.07224(17) 0.15537(13) 0.0396(4) Uani 1 1 d . . . . .
H25 H 0.412161 -0.085429 0.161691 0.048 Uiso 1 1 calc R U . . .
C26 C 0.6263(3) -0.10652(15) 0.06989(12) 0.0356(4) Uani 1 1 d . . . . .
C27 C 0.8299(3) -0.08472(16) 0.06305(12) 0.0366(4) Uani 1 1 d . . . . .
H27 H 0.883198 -0.105723 0.006055 0.044 Uiso 1 1 calc R U . . .
C28 C 0.9569(2) -0.03259(15) 0.13841(11) 0.0321(3) Uani 1 1 d . . . . .
H28 H 1.094797 -0.018708 0.132298 0.038 Uiso 1 1 calc R U . . .
C29 C 0.4887(3) -0.16721(19) -0.01219(15) 0.0498(5) Uani 1 1 d . . . . .
H29A H 0.534328 -0.140791 -0.064406 0.075 Uiso 1 1 calc R U . . .
H29B H 0.354051 -0.146621 -0.001359 0.075 Uiso 1 1 calc R U . . .
H29C H 0.489835 -0.253074 -0.023339 0.075 Uiso 1 1 calc R U . . .


_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
N1 C17 1.145(2) . ?
N2 C22 1.3463(19) . ?
N2 C18 1.3492(19) . ?
N2 H2 0.8700 . ?
C1 C2 1.412(2) . ?
C1 C14 1.416(2) . ?
C1 C15 1.485(2) . ?
C2 C3 1.430(2) . ?
C2 C7 1.438(2) . ?
C3 C4 1.359(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.347(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.431(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.390(2) . ?
C8 C9 1.397(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.429(2) . ?
C9 C14 1.434(2) . ?
C10 C11 1.352(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.415(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.359(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.428(2) . ?
C13 H13 0.9400 . ?
C15 C16 1.340(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.443(2) . ?
C16 C18 1.4800(19) . ?
C18 C19 1.387(2) . ?
C19 C20 1.386(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.384(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.371(2) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
S1 O3 1.4454(12) . ?
S1 O2 1.4510(12) . ?
S1 O1 1.4772(12) . ?
S1 C23 1.7750(18) . ?
C23 C24 1.382(2) . ?
C23 C28 1.385(2) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.402(3) . ?
C25 H25 0.9400 . ?
C26 C27 1.384(3) . ?
C26 C29 1.516(3) . ?
C27 C28 1.386(3) . ?
C27 H27 0.9400 . ?
C28 H28 0.9400 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 0.9700 . ?

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
C22 N2 C18 122.92(13) . . ?
C22 N2 H2 118.5 . . ?
C18 N2 H2 118.5 . . ?
C2 C1 C14 120.42(13) . . ?
C2 C1 C15 120.99(13) . . ?
C14 C1 C15 118.57(14) . . ?
C1 C2 C3 123.14(14) . . ?
C1 C2 C7 118.97(14) . . ?
C3 C2 C7 117.88(14) . . ?
C4 C3 C2 120.91(15) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.98(16) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 120.27(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.29(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 121.31(15) . . ?
C8 C7 C2 120.05(15) . . ?
C6 C7 C2 118.64(15) . . ?
C7 C8 C9 121.59(14) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 121.52(15) . . ?
C8 C9 C14 119.19(15) . . ?
C10 C9 C14 119.29(15) . . ?
C11 C10 C9 120.70(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.24(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 121.17(16) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.77(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C1 C14 C13 122.38(14) . . ?
C1 C14 C9 119.78(14) . . ?
C13 C14 C9 117.83(14) . . ?
C16 C15 C1 124.36(14) . . ?
C16 C15 H15 117.8 . . ?
C1 C15 H15 117.8 . . ?
C15 C16 C17 119.34(14) . . ?
C15 C16 C18 127.15(14) . . ?
C17 C16 C18 113.39(13) . . ?
N1 C17 C16 174.52(17) . . ?
N2 C18 C19 118.00(13) . . ?
N2 C18 C16 119.82(13) . . ?
C19 C18 C16 122.16(13) . . ?
C20 C19 C18 120.23(15) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.73(15) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C22 C21 C20 118.85(15) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
N2 C22 C21 120.25(14) . . ?
N2 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
O3 S1 O2 114.37(7) . . ?
O3 S1 O1 112.29(7) . . ?
O2 S1 O1 111.67(7) . . ?
O3 S1 C23 107.01(8) . . ?
O2 S1 C23 105.72(7) . . ?
O1 S1 C23 104.99(7) . . ?
C24 C23 C28 119.53(16) . . ?
C24 C23 S1 118.59(12) . . ?
C28 C23 S1 121.89(12) . . ?
C23 C24 C25 120.55(16) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.43(16) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 118.17(17) . . ?
C27 C26 C29 121.27(17) . . ?
C25 C26 C29 120.55(17) . . ?
C26 C27 C28 121.43(16) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C23 C28 C27 119.85(15) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

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
C14 C1 C2 C3 179.55(15) . . . . ?
C15 C1 C2 C3 1.4(2) . . . . ?
C14 C1 C2 C7 0.9(2) . . . . ?
C15 C1 C2 C7 -177.21(14) . . . . ?
C1 C2 C3 C4 179.84(16) . . . . ?
C7 C2 C3 C4 -1.5(2) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 -179.28(19) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C1 C2 C7 C8 -0.8(2) . . . . ?
C3 C2 C7 C8 -179.52(15) . . . . ?
C1 C2 C7 C6 178.99(16) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C6 C7 C8 C9 -179.87(17) . . . . ?
C2 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -178.84(16) . . . . ?
C7 C8 C9 C14 0.8(3) . . . . ?
C8 C9 C10 C11 179.77(18) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C2 C1 C14 C13 178.67(15) . . . . ?
C15 C1 C14 C13 -3.2(2) . . . . ?
C2 C1 C14 C9 -0.2(2) . . . . ?
C15 C1 C14 C9 178.01(14) . . . . ?
C12 C13 C14 C1 -179.45(16) . . . . ?
C12 C13 C14 C9 -0.6(2) . . . . ?
C8 C9 C14 C1 -0.7(2) . . . . ?
C10 C9 C14 C1 178.97(15) . . . . ?
C8 C9 C14 C13 -179.61(16) . . . . ?
C10 C9 C14 C13 0.1(2) . . . . ?
C2 C1 C15 C16 -67.9(2) . . . . ?
C14 C1 C15 C16 113.92(18) . . . . ?
C1 C15 C16 C17 -4.1(2) . . . . ?
C1 C15 C16 C18 -179.82(14) . . . . ?
C22 N2 C18 C19 -1.0(2) . . . . ?
C22 N2 C18 C16 177.34(14) . . . . ?
C15 C16 C18 N2 13.6(2) . . . . ?
C17 C16 C18 N2 -162.26(13) . . . . ?
C15 C16 C18 C19 -168.10(16) . . . . ?
C17 C16 C18 C19 16.0(2) . . . . ?
N2 C18 C19 C20 0.6(2) . . . . ?
C16 C18 C19 C20 -177.74(14) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C22 -1.1(3) . . . . ?
C18 N2 C22 C21 0.4(2) . . . . ?
C20 C21 C22 N2 0.7(2) . . . . ?
O3 S1 C23 C24 173.91(12) . . . . ?
O2 S1 C23 C24 51.60(14) . . . . ?
O1 S1 C23 C24 -66.59(14) . . . . ?
O3 S1 C23 C28 -5.75(15) . . . . ?
O2 S1 C23 C28 -128.06(13) . . . . ?
O1 S1 C23 C28 113.75(14) . . . . ?
C28 C23 C24 C25 2.3(3) . . . . ?
S1 C23 C24 C25 -177.36(13) . . . . ?
C23 C24 C25 C26 -1.2(3) . . . . ?
C24 C25 C26 C27 -0.6(3) . . . . ?
C24 C25 C26 C29 178.64(16) . . . . ?
C25 C26 C27 C28 1.2(3) . . . . ?
C29 C26 C27 C28 -177.97(16) . . . . ?
C24 C23 C28 C27 -1.6(2) . . . . ?
S1 C23 C28 C27 178.01(12) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.87 1.84 2.6766(18) 160.2 . yes

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_SPA670
_database_code_depnum_ccdc_archive 'CCDC 2128860'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2021-12-15 deposited with the CCDC.	2022-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 N2'
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.045(3)
_cell_length_b                   12.833(3)
_cell_length_c                   17.198(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3099.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    84582
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.061
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.938
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27810
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.099
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3918
_reflns_number_gt                2270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3918
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_restrained_S_all      0.904
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.60104(11) 0.67966(10) 0.44045(9) 0.0487(4) Uani 1 1 d . . . . .
N2 N 0.46166(12) 0.28123(11) 0.31417(9) 0.0525(4) Uani 1 1 d . . . . .
C1 C 0.59454(11) 0.46275(11) 0.41959(8) 0.0296(3) Uani 1 1 d . . . . .
C2 C 0.55998(13) 0.53014(12) 0.36349(9) 0.0402(4) Uani 1 1 d . . . . .
H2 H 0.532864 0.504063 0.317460 0.048 Uiso 1 1 calc R U . . .
C3 C 0.56589(14) 0.63682(13) 0.37612(11) 0.0494(5) Uani 1 1 d . . . . .
H3 H 0.543695 0.681514 0.336794 0.059 Uiso 1 1 calc R U . . .
C4 C 0.63247(12) 0.61405(12) 0.49429(10) 0.0415(4) Uani 1 1 d . . . . .
H4 H 0.657548 0.642401 0.540343 0.050 Uiso 1 1 calc R U . . .
C5 C 0.63076(11) 0.50638(12) 0.48711(9) 0.0353(4) Uani 1 1 d . . . . .
H5 H 0.653788 0.463737 0.527378 0.042 Uiso 1 1 calc R U . . .
C6 C 0.59152(11) 0.34807(11) 0.40862(8) 0.0298(3) Uani 1 1 d . . . . .
C7 C 0.51962(13) 0.30953(11) 0.35559(9) 0.0358(4) Uani 1 1 d . . . . .
C8 C 0.64923(11) 0.28021(11) 0.44444(9) 0.0319(4) Uani 1 1 d . . . . .
H8 H 0.695269 0.307871 0.478312 0.038 Uiso 1 1 calc R U . . .
C9 C 0.64692(10) 0.16539(11) 0.43538(8) 0.0297(3) Uani 1 1 d . . . . .
C10 C 0.66505(11) 0.11860(11) 0.36264(9) 0.0319(4) Uani 1 1 d . . . . .
C11 C 0.69235(12) 0.17489(13) 0.29471(9) 0.0405(4) Uani 1 1 d . . . . .
H11 H 0.699924 0.247554 0.297757 0.049 Uiso 1 1 calc R U . . .
C12 C 0.70761(13) 0.12640(15) 0.22601(10) 0.0492(5) Uani 1 1 d . . . . .
H12 H 0.725966 0.165579 0.182328 0.059 Uiso 1 1 calc R U . . .
C13 C 0.69618(14) 0.01695(15) 0.21930(10) 0.0484(5) Uani 1 1 d . . . . .
H13 H 0.704543 -0.015681 0.170847 0.058 Uiso 1 1 calc R U . . .
C14 C 0.67344(13) -0.04005(13) 0.28196(10) 0.0432(4) Uani 1 1 d . . . . .
H14 H 0.666921 -0.112617 0.276800 0.052 Uiso 1 1 calc R U . . .
C15 C 0.65893(11) 0.00672(11) 0.35619(9) 0.0328(4) Uani 1 1 d . . . . .
C16 C 0.63848(11) -0.05203(11) 0.42182(9) 0.0349(4) Uani 1 1 d . . . . .
H16 H 0.634478 -0.124865 0.417057 0.042 Uiso 1 1 calc R U . . .
C17 C 0.62369(11) -0.00710(11) 0.49429(9) 0.0319(4) Uani 1 1 d . . . . .
C18 C 0.60341(12) -0.06778(13) 0.56138(9) 0.0385(4) Uani 1 1 d . . . . .
H18 H 0.600840 -0.140733 0.556955 0.046 Uiso 1 1 calc R U . . .
C19 C 0.58772(13) -0.02321(14) 0.63136(10) 0.0439(4) Uani 1 1 d . . . . .
H19 H 0.574966 -0.064946 0.675052 0.053 Uiso 1 1 calc R U . . .
C20 C 0.59058(13) 0.08703(14) 0.63864(10) 0.0438(4) Uani 1 1 d . . . . .
H20 H 0.579588 0.117979 0.687362 0.053 Uiso 1 1 calc R U . . .
C21 C 0.60897(12) 0.14796(12) 0.57617(9) 0.0368(4) Uani 1 1 d . . . . .
H21 H 0.609670 0.220746 0.582278 0.044 Uiso 1 1 calc R U . . .
C22 C 0.62727(10) 0.10466(11) 0.50152(9) 0.0298(3) Uani 1 1 d . . . . .


_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
N1 C4 1.327(2) . ?
N1 C3 1.330(2) . ?
N2 C7 1.141(2) . ?
C1 C2 1.384(2) . ?
C1 C5 1.386(2) . ?
C1 C6 1.4843(19) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9400 . ?
C3 H3 0.9400 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C8 1.340(2) . ?
C6 C7 1.448(2) . ?
C8 C9 1.4820(19) . ?
C8 H8 0.9400 . ?
C9 C22 1.4062(19) . ?
C9 C10 1.411(2) . ?
C10 C11 1.426(2) . ?
C10 C15 1.442(2) . ?
C11 C12 1.352(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.418(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.341(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.425(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.421(2) . ?
C17 C22 1.440(2) . ?
C18 C19 1.351(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.421(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.354(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.422(2) . ?
C21 H21 0.9400 . ?

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 N1 C3 116.19(14) . . ?
C2 C1 C5 117.42(14) . . ?
C2 C1 C6 121.41(14) . . ?
C5 C1 C6 121.17(13) . . ?
C1 C2 C3 119.09(16) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C3 C2 124.04(17) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C5 124.33(16) . . ?
N1 C4 H4 117.8 . . ?
C5 C4 H4 117.8 . . ?
C1 C5 C4 118.90(15) . . ?
C1 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C8 C6 C7 119.31(13) . . ?
C8 C6 C1 124.67(14) . . ?
C7 C6 C1 116.02(13) . . ?
N2 C7 C6 178.35(18) . . ?
C6 C8 C9 125.78(14) . . ?
C6 C8 H8 117.1 . . ?
C9 C8 H8 117.1 . . ?
C22 C9 C10 121.11(13) . . ?
C22 C9 C8 118.06(13) . . ?
C10 C9 C8 120.83(13) . . ?
C9 C10 C11 124.01(14) . . ?
C9 C10 C15 118.76(13) . . ?
C11 C10 C15 117.21(14) . . ?
C12 C11 C10 121.68(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.58(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.11(16) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.61(15) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 121.97(14) . . ?
C16 C15 C10 119.38(14) . . ?
C14 C15 C10 118.65(14) . . ?
C15 C16 C17 122.37(13) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C18 122.09(14) . . ?
C16 C17 C22 119.05(13) . . ?
C18 C17 C22 118.85(14) . . ?
C19 C18 C17 121.62(15) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.71(15) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 120.70(16) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 121.68(15) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C9 C22 C21 123.30(13) . . ?
C9 C22 C17 119.27(13) . . ?
C21 C22 C17 117.43(13) . . ?

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
C5 C1 C2 C3 2.0(2) . . . . ?
C6 C1 C2 C3 -178.98(15) . . . . ?
C4 N1 C3 C2 0.6(3) . . . . ?
C1 C2 C3 N1 -1.7(3) . . . . ?
C3 N1 C4 C5 0.1(3) . . . . ?
C2 C1 C5 C4 -1.4(2) . . . . ?
C6 C1 C5 C4 179.64(14) . . . . ?
N1 C4 C5 C1 0.3(3) . . . . ?
C2 C1 C6 C8 156.30(16) . . . . ?
C5 C1 C6 C8 -24.8(2) . . . . ?
C2 C1 C6 C7 -24.3(2) . . . . ?
C5 C1 C6 C7 154.63(14) . . . . ?
C7 C6 C8 C9 -0.3(2) . . . . ?
C1 C6 C8 C9 179.13(14) . . . . ?
C6 C8 C9 C22 -118.21(17) . . . . ?
C6 C8 C9 C10 62.5(2) . . . . ?
C22 C9 C10 C11 -175.14(15) . . . . ?
C8 C9 C10 C11 4.1(2) . . . . ?
C22 C9 C10 C15 2.8(2) . . . . ?
C8 C9 C10 C15 -178.01(14) . . . . ?
C9 C10 C11 C12 -179.05(16) . . . . ?
C15 C10 C11 C12 3.0(2) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -2.5(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 -177.84(17) . . . . ?
C13 C14 C15 C10 2.7(2) . . . . ?
C9 C10 C15 C16 -2.0(2) . . . . ?
C11 C10 C15 C16 176.01(14) . . . . ?
C9 C10 C15 C14 177.46(14) . . . . ?
C11 C10 C15 C14 -4.5(2) . . . . ?
C14 C15 C16 C17 -179.63(15) . . . . ?
C10 C15 C16 C17 -0.1(2) . . . . ?
C15 C16 C17 C18 -179.56(15) . . . . ?
C15 C16 C17 C22 1.6(2) . . . . ?
C16 C17 C18 C19 -178.98(16) . . . . ?
C22 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C10 C9 C22 C21 179.70(15) . . . . ?
C8 C9 C22 C21 0.4(2) . . . . ?
C10 C9 C22 C17 -1.3(2) . . . . ?
C8 C9 C22 C17 179.43(13) . . . . ?
C20 C21 C22 C9 -179.80(16) . . . . ?
C20 C21 C22 C17 1.2(2) . . . . ?
C16 C17 C22 C9 -0.9(2) . . . . ?
C18 C17 C22 C9 -179.75(14) . . . . ?
C16 C17 C22 C21 178.17(14) . . . . ?
C18 C17 C22 C21 -0.7(2) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049

