# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_SPA401
_database_code_depnum_ccdc_archive 'CCDC 1945296'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   13.200(3)
_cell_length_b                   12.855(3)
_cell_length_c                   11.449(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1942.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    61611
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.055
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.930
_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     0.610
_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            19074
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_av_R_equivalents  0.0646
_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       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_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             5406
_reflns_number_gt                5014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5406
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.09038(12) 0.37326(12) 0.38755(15) 0.0274(3) Uani 1 1 d . . . . .
N2 N 0.41631(14) 0.43893(18) 0.86914(17) 0.0474(5) Uani 1 1 d . . . . .
C1 C 0.01190(12) 0.44361(14) 0.40658(16) 0.0254(3) Uani 1 1 d . . . . .
C2 C 0.00831(14) 0.52845(14) 0.48215(18) 0.0305(4) Uani 1 1 d . . . . .
H2 H 0.063015 0.544452 0.531557 0.037 Uiso 1 1 calc R U . . .
C3 C -0.07872(15) 0.58820(15) 0.4817(2) 0.0353(4) Uani 1 1 d . . . . .
H3 H -0.083015 0.646031 0.531752 0.042 Uiso 1 1 calc R U . . .
C4 C -0.16078(15) 0.56470(16) 0.4086(2) 0.0380(5) Uani 1 1 d . . . . .
H4 H -0.219062 0.606684 0.410441 0.046 Uiso 1 1 calc R U . . .
C5 C -0.15682(14) 0.48052(14) 0.33385(18) 0.0333(4) Uani 1 1 d . . . . .
H5 H -0.212146 0.464632 0.285339 0.040 Uiso 1 1 calc R U . . .
C6 C -0.06939(13) 0.41927(13) 0.33134(16) 0.0259(3) Uani 1 1 d . . . . .
C7 C -0.03843(14) 0.32980(14) 0.26298(15) 0.0271(3) Uani 1 1 d . . . . .
C8 C -0.08520(16) 0.26959(16) 0.17758(16) 0.0336(4) Uani 1 1 d . . . . .
H8 H -0.151057 0.285805 0.152183 0.040 Uiso 1 1 calc R U . . .
C9 C -0.03378(18) 0.18539(17) 0.13025(17) 0.0394(5) Uani 1 1 d . . . . .
H9 H -0.064577 0.144785 0.071925 0.047 Uiso 1 1 calc R U . . .
C10 C 0.06404(19) 0.16077(16) 0.16924(18) 0.0386(5) Uani 1 1 d . . . . .
H10 H 0.097715 0.103166 0.136824 0.046 Uiso 1 1 calc R U . . .
C11 C 0.11210(15) 0.21903(14) 0.25406(18) 0.0334(4) Uani 1 1 d . . . . .
H11 H 0.177533 0.201696 0.279976 0.040 Uiso 1 1 calc R U . . .
C12 C 0.06064(14) 0.30423(13) 0.29998(16) 0.0265(3) Uani 1 1 d . . . . .
C13 C 0.18818(14) 0.37677(13) 0.43926(16) 0.0254(4) Uani 1 1 d . . . . .
C14 C 0.19880(15) 0.37335(15) 0.56034(17) 0.0299(4) Uani 1 1 d . . . . .
H14 H 0.141020 0.370472 0.608225 0.036 Uiso 1 1 calc R U . . .
C15 C 0.29446(15) 0.37417(15) 0.61013(16) 0.0298(4) Uani 1 1 d . . . . .
H15 H 0.301013 0.372922 0.691877 0.036 Uiso 1 1 calc R U . . .
C16 C 0.38182(13) 0.37686(13) 0.54003(16) 0.0255(4) Uani 1 1 d . . . . .
C17 C 0.36888(14) 0.38057(14) 0.41853(16) 0.0278(4) Uani 1 1 d . . . . .
H17 H 0.426303 0.382338 0.370008 0.033 Uiso 1 1 calc R U . . .
C18 C 0.27334(14) 0.38168(14) 0.36841(16) 0.0279(4) Uani 1 1 d . . . . .
H18 H 0.266250 0.385740 0.286845 0.033 Uiso 1 1 calc R U . . .
C19 C 0.48598(14) 0.37225(14) 0.58260(17) 0.0280(4) Uani 1 1 d . . . . .
H19 H 0.534405 0.356811 0.524948 0.034 Uiso 1 1 calc R U . . .
C20 C 0.52467(14) 0.38639(14) 0.69069(17) 0.0272(4) Uani 1 1 d . . . . .
C21 C 0.46219(15) 0.41360(16) 0.78894(18) 0.0324(4) Uani 1 1 d . . . . .
C22 C 0.63492(14) 0.37823(14) 0.71672(18) 0.0288(4) Uani 1 1 d . . . . .
C23 C 0.66763(16) 0.34524(16) 0.8265(2) 0.0371(4) Uani 1 1 d . . . . .
H23 H 0.619896 0.329772 0.884884 0.044 Uiso 1 1 calc R U . . .
C24 C 0.77055(19) 0.33513(18) 0.8499(2) 0.0458(5) Uani 1 1 d . . . . .
H24 H 0.792040 0.312512 0.923959 0.055 Uiso 1 1 calc R U . . .
C25 C 0.84096(16) 0.35805(18) 0.7653(3) 0.0468(6) Uani 1 1 d . . . . .
H25 H 0.910412 0.350957 0.781651 0.056 Uiso 1 1 calc R U . . .
C26 C 0.80997(16) 0.3914(2) 0.6566(3) 0.0452(6) Uani 1 1 d . . . . .
H26 H 0.858351 0.406761 0.598821 0.054 Uiso 1 1 calc R U . . .
C27 C 0.70744(16) 0.40248(18) 0.6321(2) 0.0371(4) Uani 1 1 d . . . . .
H27 H 0.686767 0.426377 0.558225 0.045 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 C1 1.392(2) . ?
N1 C12 1.395(2) . ?
N1 C13 1.421(2) . ?
N2 C21 1.147(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.411(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.450(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.413(2) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.402(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.392(3) . ?
C11 H11 0.9400 . ?
C13 C18 1.388(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.405(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.402(2) . ?
C16 C19 1.460(2) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.351(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.438(3) . ?
C20 C22 1.489(3) . ?
C22 C23 1.395(3) . ?
C22 C27 1.397(3) . ?
C23 C24 1.391(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.374(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.379(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.389(3) . ?
C26 H26 0.9400 . ?
C27 H27 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
C1 N1 C12 108.43(15) . . ?
C1 N1 C13 126.17(15) . . ?
C12 N1 C13 125.12(15) . . ?
N1 C1 C2 129.13(16) . . ?
N1 C1 C6 109.04(15) . . ?
C2 C1 C6 121.80(16) . . ?
C3 C2 C1 117.47(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.63(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.65(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.06(16) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.38(16) . . ?
C5 C6 C7 133.70(16) . . ?
C1 C6 C7 106.92(15) . . ?
C8 C7 C12 119.46(18) . . ?
C8 C7 C6 134.05(18) . . ?
C12 C7 C6 106.47(15) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.14(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 121.64(19) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 117.92(19) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 N1 129.39(17) . . ?
C11 C12 C7 121.42(16) . . ?
N1 C12 C7 109.13(15) . . ?
C18 C13 C14 120.08(18) . . ?
C18 C13 N1 119.60(16) . . ?
C14 C13 N1 120.31(17) . . ?
C15 C14 C13 120.04(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.86(17) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 117.87(17) . . ?
C17 C16 C19 116.56(17) . . ?
C15 C16 C19 125.53(17) . . ?
C18 C17 C16 121.46(17) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 119.66(17) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C20 C19 C16 131.01(17) . . ?
C20 C19 H19 114.5 . . ?
C16 C19 H19 114.5 . . ?
C19 C20 C21 122.17(18) . . ?
C19 C20 C22 122.90(17) . . ?
C21 C20 C22 114.90(17) . . ?
N2 C21 C20 176.4(2) . . ?
C23 C22 C27 118.72(19) . . ?
C23 C22 C20 120.28(19) . . ?
C27 C22 C20 121.00(18) . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.2(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C27 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?

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
C12 N1 C1 C2 -177.42(18) . . . . ?
C13 N1 C1 C2 -3.3(3) . . . . ?
C12 N1 C1 C6 0.5(2) . . . . ?
C13 N1 C1 C6 174.56(17) . . . . ?
N1 C1 C2 C3 178.1(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
N1 C1 C6 C5 -179.26(17) . . . . ?
C2 C1 C6 C5 -1.2(3) . . . . ?
N1 C1 C6 C7 -0.19(19) . . . . ?
C2 C1 C6 C7 177.87(17) . . . . ?
C5 C6 C7 C8 -2.6(4) . . . . ?
C1 C6 C7 C8 178.5(2) . . . . ?
C5 C6 C7 C12 178.73(19) . . . . ?
C1 C6 C7 C12 -0.14(19) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C6 C7 C8 C9 -178.46(19) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 N1 178.05(19) . . . . ?
C10 C11 C12 C7 1.1(3) . . . . ?
C1 N1 C12 C11 -177.78(19) . . . . ?
C13 N1 C12 C11 8.0(3) . . . . ?
C1 N1 C12 C7 -0.5(2) . . . . ?
C13 N1 C12 C7 -174.73(16) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C6 C7 C12 C11 177.92(16) . . . . ?
C8 C7 C12 N1 -178.46(16) . . . . ?
C6 C7 C12 N1 0.4(2) . . . . ?
C1 N1 C13 C18 -122.1(2) . . . . ?
C12 N1 C13 C18 51.0(2) . . . . ?
C1 N1 C13 C14 59.1(3) . . . . ?
C12 N1 C13 C14 -127.8(2) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
N1 C13 C14 C15 178.38(15) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C14 C15 C16 C19 -176.46(17) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C19 C16 C17 C18 177.88(15) . . . . ?
C16 C17 C18 C13 -1.4(3) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
N1 C13 C18 C17 -177.22(16) . . . . ?
C17 C16 C19 C20 166.6(2) . . . . ?
C15 C16 C19 C20 -15.7(3) . . . . ?
C16 C19 C20 C21 -1.9(3) . . . . ?
C16 C19 C20 C22 179.99(18) . . . . ?
C19 C20 C22 C23 -149.9(2) . . . . ?
C21 C20 C22 C23 31.8(2) . . . . ?
C19 C20 C22 C27 29.6(3) . . . . ?
C21 C20 C22 C27 -148.69(19) . . . . ?
C27 C22 C23 C24 -1.1(3) . . . . ?
C20 C22 C23 C24 178.40(18) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C24 C25 C26 C27 0.3(4) . . . . ?
C25 C26 C27 C22 -1.1(4) . . . . ?
C23 C22 C27 C26 1.5(3) . . . . ?
C20 C22 C27 C26 -178.0(2) . . . . ?

_refine_diff_density_max         0.267
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_SPA207
_database_code_depnum_ccdc_archive 'CCDC 1945297'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 '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                   9.4870(19)
_cell_length_b                   13.015(3)
_cell_length_c                   15.666(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.28(3)
_cell_angle_gamma                90
_cell_volume                     1931.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    65917
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20482
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5651
_reflns_number_gt                4461
_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-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0780P)²+0.2192P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.066(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5651
_refine_ls_number_parameters     300
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   1.071
_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 0.20072(10) 0.72639(6) 0.36507(6) 0.01941(19) Uani 1 1 d . . . . .
N2 N 0.13427(12) 0.23510(8) 0.19905(7) 0.0311(2) Uani 1 1 d . . . . .
C1 C 0.15100(11) 0.70868(8) 0.44576(7) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.13180(12) 0.61571(8) 0.48779(7) 0.0233(2) Uani 1 1 d . . . . .
H2 H 0.148596 0.551868 0.460782 0.028 Uiso 1 1 calc R U . . .
C3 C 0.08731(13) 0.61996(9) 0.57043(7) 0.0263(2) Uani 1 1 d . . . . .
H3 H 0.073426 0.557736 0.600510 0.032 Uiso 1 1 calc R U . . .
C4 C 0.06224(13) 0.71404(9) 0.61081(7) 0.0264(2) Uani 1 1 d . . . . .
H4 H 0.030378 0.714607 0.667208 0.032 Uiso 1 1 calc R U . . .
C5 C 0.08363(12) 0.80576(8) 0.56905(7) 0.0234(2) Uani 1 1 d . . . . .
H5 H 0.068241 0.869366 0.596773 0.028 Uiso 1 1 calc R U . . .
C6 C 0.12810(11) 0.80390(8) 0.48562(7) 0.0197(2) Uani 1 1 d . . . . .
C7 C 0.16482(11) 0.88304(8) 0.42612(7) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.16461(12) 0.99045(8) 0.42899(7) 0.0223(2) Uani 1 1 d . . . . .
H8 H 0.137764 1.025454 0.478743 0.027 Uiso 1 1 calc R U . . .
C9 C 0.20413(12) 1.04521(8) 0.35820(8) 0.0243(2) Uani 1 1 d . . . . .
H9 H 0.204030 1.118187 0.359403 0.029 Uiso 1 1 calc R U . . .
C10 C 0.24415(12) 0.99355(8) 0.28502(8) 0.0234(2) Uani 1 1 d . . . . .
H10 H 0.268601 1.032391 0.236698 0.028 Uiso 1 1 calc R U . . .
C11 C 0.24903(11) 0.88710(8) 0.28125(7) 0.0214(2) Uani 1 1 d . . . . .
H11 H 0.278571 0.852646 0.231887 0.026 Uiso 1 1 calc R U . . .
C12 C 0.20904(11) 0.83261(7) 0.35245(7) 0.0186(2) Uani 1 1 d . . . . .
C13 C 0.23781(11) 0.64993(7) 0.30601(7) 0.0187(2) Uani 1 1 d . . . . .
C14 C 0.36925(12) 0.65329(8) 0.27062(7) 0.0224(2) Uani 1 1 d . . . . .
H14 H 0.435077 0.705615 0.287180 0.027 Uiso 1 1 calc R U . . .
C15 C 0.40335(11) 0.57984(8) 0.21110(7) 0.0216(2) Uani 1 1 d . . . . .
H15 H 0.491203 0.584306 0.185119 0.026 Uiso 1 1 calc R U . . .
C16 C 0.31067(11) 0.49905(7) 0.18847(7) 0.0185(2) Uani 1 1 d . . . . .
C17 C 0.17857(11) 0.49682(7) 0.22485(7) 0.0187(2) Uani 1 1 d . . . . .
H17 H 0.113625 0.443309 0.209983 0.022 Uiso 1 1 calc R U . . .
C18 C 0.14239(11) 0.57217(7) 0.28229(7) 0.0188(2) Uani 1 1 d . . . . .
H18 H 0.052123 0.570778 0.305572 0.023 Uiso 1 1 calc R U . . .
C19 C 0.35542(11) 0.42643(7) 0.12397(7) 0.0191(2) Uani 1 1 d . . . . .
H19 H 0.426406 0.451194 0.088851 0.023 Uiso 1 1 calc R U . . .
C20 C 0.31111(11) 0.32948(8) 0.10676(7) 0.0185(2) Uani 1 1 d . . . . .
C21 C 0.21089(12) 0.27918(7) 0.15856(7) 0.0214(2) Uani 1 1 d . . . . .
C22A C 0.35787(19) 0.26920(13) 0.03304(12) 0.0169(3) Uani 0.883(3) 1 d . . P A
1
C23A C 0.26603(14) 0.19903(9) -0.00745(8) 0.0229(3) Uani 0.883(3) 1 d . . P A 1
H23A H 0.175720 0.187324 0.013952 0.028 Uiso 0.883(3) 1 calc R U P A 1
C24A C 0.30598(15) 0.14591(10) -0.07920(9) 0.0281(3) Uani 0.883(3) 1 d . . P A
1
H24A H 0.241497 0.099927 -0.107854 0.034 Uiso 0.883(3) 1 calc R U P A 1
C25A C 0.43924(16) 0.15967(10) -0.10913(9) 0.0269(3) Uani 0.883(3) 1 d . . P A
1
H25A H 0.466075 0.123088 -0.158100 0.032 Uiso 0.883(3) 1 calc R U P A 1
C26A C 0.53312(13) 0.22669(9) -0.06765(8) 0.0259(2) Uani 0.883(3) 1 d . . P A 1
H26A H 0.625903 0.234188 -0.086623 0.031 Uiso 0.883(3) 1 calc R U P A 1
C27A C 0.49145(12) 0.28301(8) 0.00180(7) 0.0234(2) Uani 0.883(3) 1 d . . P A 1
H27A H 0.554583 0.331538 0.028387 0.028 Uiso 0.883(3) 1 calc R U P A 1
C22B C 0.3797(16) 0.2523(12) 0.0476(10) 0.020(4) Uani 0.117(3) 1 d . U P A 2
C23B C 0.3461(13) 0.1437(9) 0.0455(9) 0.048(4) Uani 0.117(3) 1 d . . P A 2
H23B H 0.279693 0.117570 0.083190 0.058 Uiso 0.117(3) 1 calc R U P A 2
C24B C 0.4081(15) 0.0774(11) -0.0098(11) 0.070(6) Uani 0.117(3) 1 d . . P A 2
H24B H 0.387686 0.005987 -0.007725 0.083 Uiso 0.117(3) 1 calc R U P A 2
C25B C 0.5012(15) 0.1146(10) -0.0691(10) 0.046(4) Uani 0.117(3) 1 d . . P A 2
H25B H 0.542301 0.069903 -0.108648 0.055 Uiso 0.117(3) 1 calc R U P A 2
C26B C 0.53312(13) 0.22669(9) -0.06765(8) 0.0259(2) Uani 0.117(3) 1 d . . P A 2
H26B H 0.580249 0.258429 -0.112608 0.031 Uiso 0.117(3) 1 calc R U P A 2
C27B C 0.49145(12) 0.28301(8) 0.00180(7) 0.0234(2) Uani 0.117(3) 1 d . . P A 2
H27B H 0.541191 0.343977 0.017941 0.028 Uiso 0.117(3) 1 calc R U P A 2


_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 C1 1.3934(13) . ?
N1 C12 1.3994(12) . ?
N1 C13 1.4169(12) . ?
N2 C21 1.1456(15) . ?
C1 C2 1.3944(14) . ?
C1 C6 1.4102(14) . ?
C2 C3 1.3856(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4047(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3819(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3963(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4452(14) . ?
C7 C8 1.3986(14) . ?
C7 C12 1.4122(14) . ?
C8 C9 1.3878(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4001(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3876(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3926(14) . ?
C11 H11 0.9500 . ?
C13 C18 1.3940(14) . ?
C13 C14 1.3941(15) . ?
C14 C15 1.3866(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.4030(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.4065(14) . ?
C16 C19 1.4642(14) . ?
C17 C18 1.3873(13) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3522(14) . ?
C19 H19 0.9500 . ?
C20 C21 1.4421(14) . ?
C20 C22A 1.4847(18) . ?
C20 C22B 1.536(16) . ?
C22A C23A 1.390(2) . ?
C22A C27A 1.396(2) . ?
C23A C24A 1.3906(17) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.3849(19) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.3821(18) . ?
C25A H25A 0.9500 . ?
C26A C27A 1.3881(15) . ?
C26A H26A 0.9500 . ?
C27A H27A 0.9500 . ?
C22B C27B 1.373(16) . ?
C22B C23B 1.450(19) . ?
C23B C24B 1.378(17) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.404(19) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.490(13) . ?
C25B H25B 0.9500 . ?
C26B C27B 1.3881(15) . ?
C26B H26B 0.9500 . ?
C27B H27B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.45(8) . . ?
C1 N1 C13 125.86(8) . . ?
C12 N1 C13 125.69(8) . . ?
N1 C1 C2 129.20(9) . . ?
N1 C1 C6 108.97(9) . . ?
C2 C1 C6 121.72(10) . . ?
C3 C2 C1 117.49(10) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.61(10) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.43(10) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.25(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 119.49(10) . . ?
C5 C6 C7 133.49(9) . . ?
C1 C6 C7 106.96(9) . . ?
C8 C7 C12 119.47(10) . . ?
C8 C7 C6 133.69(10) . . ?
C12 C7 C6 106.84(9) . . ?
C9 C8 C7 119.11(10) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.40(10) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 121.71(10) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.59(10) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 N1 129.53(9) . . ?
C11 C12 C7 121.68(9) . . ?
N1 C12 C7 108.77(9) . . ?
C18 C13 C14 119.92(9) . . ?
C18 C13 N1 120.15(9) . . ?
C14 C13 N1 119.93(9) . . ?
C15 C14 C13 119.62(10) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.31(10) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C17 118.24(9) . . ?
C15 C16 C19 117.12(9) . . ?
C17 C16 C19 124.51(9) . . ?
C18 C17 C16 120.50(9) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.34(9) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C20 C19 C16 129.86(10) . . ?
C20 C19 H19 115.1 . . ?
C16 C19 H19 115.1 . . ?
C19 C20 C21 121.26(9) . . ?
C19 C20 C22A 123.01(10) . . ?
C21 C20 C22A 115.71(10) . . ?
C19 C20 C22B 126.3(6) . . ?
C21 C20 C22B 111.0(6) . . ?
N2 C21 C20 176.90(11) . . ?
C23A C22A C27A 118.84(13) . . ?
C23A C22A C20 119.66(13) . . ?
C27A C22A C20 121.48(13) . . ?
C22A C23A C24A 120.18(12) . . ?
C22A C23A H23A 119.9 . . ?
C24A C23A H23A 119.9 . . ?
C25A C24A C23A 120.38(12) . . ?
C25A C24A H24A 119.8 . . ?
C23A C24A H24A 119.8 . . ?
C26A C25A C24A 119.92(11) . . ?
C26A C25A H25A 120.0 . . ?
C24A C25A H25A 120.0 . . ?
C25A C26A C27A 119.80(11) . . ?
C25A C26A H26A 120.1 . . ?
C27A C26A H26A 120.1 . . ?
C26A C27A C22A 120.79(12) . . ?
C26A C27A H27A 119.6 . . ?
C22A C27A H27A 119.6 . . ?
C27B C22B C23B 116.6(12) . . ?
C27B C22B C20 119.5(11) . . ?
C23B C22B C20 123.4(12) . . ?
C24B C23B C22B 121.6(13) . . ?
C24B C23B H23B 119.2 . . ?
C22B C23B H23B 119.2 . . ?
C23B C24B C25B 120.5(12) . . ?
C23B C24B H24B 119.8 . . ?
C25B C24B H24B 119.8 . . ?
C24B C25B C26B 117.6(9) . . ?
C24B C25B H25B 121.2 . . ?
C26B C25B H25B 121.2 . . ?
C27B C26B C25B 117.5(5) . . ?
C27B C26B H26B 121.2 . . ?
C25B C26B H26B 121.2 . . ?
C22B C27B C26B 121.3(7) . . ?
C22B C27B H27B 119.4 . . ?
C26B C27B H27B 119.4 . . ?

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
C12 N1 C1 C2 -176.70(11) . . . . ?
C13 N1 C1 C2 2.80(19) . . . . ?
C12 N1 C1 C6 -0.42(12) . . . . ?
C13 N1 C1 C6 179.07(10) . . . . ?
N1 C1 C2 C3 176.67(11) . . . . ?
C6 C1 C2 C3 0.82(17) . . . . ?
C1 C2 C3 C4 0.00(18) . . . . ?
C2 C3 C4 C5 -0.98(19) . . . . ?
C3 C4 C5 C6 1.11(18) . . . . ?
C4 C5 C6 C1 -0.31(17) . . . . ?
C4 C5 C6 C7 -177.21(12) . . . . ?
N1 C1 C6 C5 -177.28(10) . . . . ?
C2 C1 C6 C5 -0.68(17) . . . . ?
N1 C1 C6 C7 0.37(12) . . . . ?
C2 C1 C6 C7 176.97(10) . . . . ?
C5 C6 C7 C8 -2.7(2) . . . . ?
C1 C6 C7 C8 -179.86(12) . . . . ?
C5 C6 C7 C12 177.01(12) . . . . ?
C1 C6 C7 C12 -0.17(12) . . . . ?
C12 C7 C8 C9 1.83(16) . . . . ?
C6 C7 C8 C9 -178.51(11) . . . . ?
C7 C8 C9 C10 -0.23(17) . . . . ?
C8 C9 C10 C11 -1.55(18) . . . . ?
C9 C10 C11 C12 1.60(17) . . . . ?
C10 C11 C12 N1 178.29(11) . . . . ?
C10 C11 C12 C7 0.06(16) . . . . ?
C1 N1 C12 C11 -178.10(11) . . . . ?
C13 N1 C12 C11 2.41(18) . . . . ?
C1 N1 C12 C7 0.31(12) . . . . ?
C13 N1 C12 C7 -179.19(10) . . . . ?
C8 C7 C12 C11 -1.79(16) . . . . ?
C6 C7 C12 C11 178.48(10) . . . . ?
C8 C7 C12 N1 179.66(10) . . . . ?
C6 C7 C12 N1 -0.08(12) . . . . ?
C1 N1 C13 C18 53.09(15) . . . . ?
C12 N1 C13 C18 -127.50(11) . . . . ?
C1 N1 C13 C14 -127.82(12) . . . . ?
C12 N1 C13 C14 51.59(15) . . . . ?
C18 C13 C14 C15 0.84(16) . . . . ?
N1 C13 C14 C15 -178.24(10) . . . . ?
C13 C14 C15 C16 -2.97(17) . . . . ?
C14 C15 C16 C17 2.89(16) . . . . ?
C14 C15 C16 C19 179.01(10) . . . . ?
C15 C16 C17 C18 -0.73(15) . . . . ?
C19 C16 C17 C18 -176.54(10) . . . . ?
C16 C17 C18 C13 -1.33(16) . . . . ?
C14 C13 C18 C17 1.28(16) . . . . ?
N1 C13 C18 C17 -179.63(9) . . . . ?
C15 C16 C19 C20 159.66(12) . . . . ?
C17 C16 C19 C20 -24.49(18) . . . . ?
C16 C19 C20 C21 -4.28(19) . . . . ?
C16 C19 C20 C22A 173.89(13) . . . . ?
C16 C19 C20 C22B -169.6(6) . . . . ?
C19 C20 C22A C23A -147.42(15) . . . . ?
C21 C20 C22A C23A 30.8(2) . . . . ?
C19 C20 C22A C27A 31.0(2) . . . . ?
C21 C20 C22A C27A -150.72(15) . . . . ?
C27A C22A C23A C24A -1.7(3) . . . . ?
C20 C22A C23A C24A 176.75(14) . . . . ?
C22A C23A C24A C25A 2.3(2) . . . . ?
C23A C24A C25A C26A -0.1(2) . . . . ?
C24A C25A C26A C27A -2.6(2) . . . . ?
C25A C26A C27A C22A 3.1(2) . . . . ?
C23A C22A C27A C26A -1.0(2) . . . . ?
C20 C22A C27A C26A -179.43(13) . . . . ?
C19 C20 C22B C27B -4.8(13) . . . . ?
C21 C20 C22B C27B -171.3(7) . . . . ?
C19 C20 C22B C23B 166.6(8) . . . . ?
C21 C20 C22B C23B 0.0(12) . . . . ?
C27B C22B C23B C24B -9.8(13) . . . . ?
C20 C22B C23B C24B 178.7(12) . . . . ?
C22B C23B C24B C25B -3.2(16) . . . . ?
C23B C24B C25B C26B 2(2) . . . . ?
C24B C25B C26B C27B 12.2(16) . . . . ?
C23B C22B C27B C26B 24.9(12) . . . . ?
C20 C22B C27B C26B -163.2(6) . . . . ?
C25B C26B C27B C22B -26.3(9) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_SPA317
_database_code_depnum_ccdc_archive 'CCDC 1945301'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 Cl N2'
_chemical_formula_sum            'C27 H17 Cl N2'
_chemical_formula_weight         404.88

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'
Cl Cl 0.1230 0.1255 '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                   16.062(3)
_cell_length_b                   15.690(3)
_cell_length_c                   8.0340(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.04(3)
_cell_angle_gamma                90
_cell_volume                     2004.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    58619
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.018
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.151
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.857
_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            19406
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.616
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             5100
_reflns_number_gt                4110
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&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)+(0.0797P)²+0.3499P] 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         5100
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.83368(2) 0.42400(2) -0.20780(5) 0.04002(12) Uani 1 1 d . . . . .
C1 C 0.16309(8) 0.36598(8) 0.26626(19) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.24681(7) 0.37951(7) 0.33741(15) 0.0269(2) Uani 1 1 d . . . . .
N2 N 0.53531(8) 0.11777(8) 0.1081(2) 0.0423(3) Uani 1 1 d . . . . .
C2 C 0.13116(10) 0.33824(10) 0.1051(2) 0.0382(3) Uani 1 1 d . . . . .
H2 H 0.166816 0.320730 0.028215 0.046 Uiso 1 1 calc R U . . .
C4 C -0.00889(10) 0.36287(14) 0.1781(3) 0.0532(5) Uani 1 1 d . . . . .
H4 H -0.067387 0.362870 0.144945 0.064 Uiso 1 1 calc R U . . .
C3 C 0.04418(11) 0.33766(13) 0.0631(2) 0.0492(4) Uani 1 1 d . . . . .
H3 H 0.020511 0.319916 -0.044956 0.059 Uiso 1 1 calc R U . . .
C5 C 0.02284(10) 0.38766(12) 0.3386(2) 0.0451(4) Uani 1 1 d . . . . .
H5 H -0.013363 0.403189 0.415804 0.054 Uiso 1 1 calc R U . . .
C6 C 0.11016(9) 0.38931(9) 0.3846(2) 0.0331(3) Uani 1 1 d . . . . .
C7 C 0.16398(9) 0.41608(9) 0.5350(2) 0.0315(3) Uani 1 1 d . . . . .
C8 C 0.14859(11) 0.44206(10) 0.6940(2) 0.0405(4) Uani 1 1 d . . . . .
H8 H 0.093288 0.445679 0.719157 0.049 Uiso 1 1 calc R U . . .
C9 C 0.21600(12) 0.46235(10) 0.8136(2) 0.0432(4) Uani 1 1 d . . . . .
H9 H 0.206331 0.479868 0.921173 0.052 Uiso 1 1 calc R U . . .
C10 C 0.29806(11) 0.45722(10) 0.7772(2) 0.0393(3) Uani 1 1 d . . . . .
H10 H 0.342729 0.471522 0.861042 0.047 Uiso 1 1 calc R U . . .
C11 C 0.31572(9) 0.43168(8) 0.62123(19) 0.0313(3) Uani 1 1 d . . . . .
H11 H 0.371296 0.428212 0.597547 0.038 Uiso 1 1 calc R U . . .
C12 C 0.24733(8) 0.41120(8) 0.50010(17) 0.0264(3) Uani 1 1 d . . . . .
C13 C 0.31844(8) 0.36944(8) 0.25500(17) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.33040(8) 0.29381(8) 0.16988(18) 0.0291(3) Uani 1 1 d . . . . .
H14 H 0.289713 0.250429 0.163515 0.035 Uiso 1 1 calc R U . . .
C15 C 0.40195(8) 0.28270(8) 0.09509(18) 0.0295(3) Uani 1 1 d . . . . .
H15 H 0.408839 0.232080 0.035932 0.035 Uiso 1 1 calc R U . . .
C16 C 0.46454(8) 0.34552(8) 0.10571(17) 0.0269(3) Uani 1 1 d . . . . .
C17 C 0.45014(8) 0.42223(8) 0.18716(18) 0.0272(3) Uani 1 1 d . . . . .
H17 H 0.490111 0.466231 0.191704 0.033 Uiso 1 1 calc R U . . .
C18 C 0.37805(8) 0.43415(8) 0.26090(18) 0.0270(3) Uani 1 1 d . . . . .
H18 H 0.369394 0.485895 0.314892 0.032 Uiso 1 1 calc R U . . .
C19 C 0.54388(8) 0.33582(8) 0.03860(18) 0.0285(3) Uani 1 1 d . . . . .
H19 H 0.568158 0.386767 0.006883 0.034 Uiso 1 1 calc R U . . .
C20 C 0.58742(8) 0.26418(8) 0.01552(16) 0.0257(3) Uani 1 1 d . . . . .
C21 C 0.55680(8) 0.18294(9) 0.06584(19) 0.0301(3) Uani 1 1 d . . . . .
C22 C 0.66942(8) 0.26139(8) -0.04949(16) 0.0251(3) Uani 1 1 d . . . . .
C23 C 0.70939(8) 0.33624(8) -0.09166(17) 0.0271(3) Uani 1 1 d . . . . .
H23 H 0.684227 0.389592 -0.079927 0.033 Uiso 1 1 calc R U . . .
C24 C 0.78591(9) 0.33099(8) -0.15051(18) 0.0286(3) Uani 1 1 d . . . . .
C25 C 0.82565(9) 0.25398(10) -0.1686(2) 0.0350(3) Uani 1 1 d . . . . .
H25 H 0.878105 0.251879 -0.207690 0.042 Uiso 1 1 calc R U . . .
C26 C 0.78599(10) 0.18010(9) -0.1275(2) 0.0381(3) Uani 1 1 d . . . . .
H26 H 0.811868 0.127081 -0.138766 0.046 Uiso 1 1 calc R U . . .
C27 C 0.70879(9) 0.18331(9) -0.07004(19) 0.0325(3) Uani 1 1 d . . . . .
H27 H 0.682449 0.132394 -0.044492 0.039 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
Cl1 C24 1.7404(14) . ?
C1 C2 1.394(2) . ?
C1 N1 1.4017(17) . ?
C1 C6 1.410(2) . ?
N1 C12 1.3974(18) . ?
N1 C13 1.4143(17) . ?
N2 C21 1.1457(19) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9400 . ?
C4 C5 1.375(3) . ?
C4 C3 1.399(3) . ?
C4 H4 0.9400 . ?
C3 H3 0.9400 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.446(2) . ?
C7 C8 1.395(2) . ?
C7 C12 1.4078(19) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9400 . ?
C13 C18 1.3917(18) . ?
C13 C14 1.3963(18) . ?
C14 C15 1.3804(19) . ?
C14 H14 0.9400 . ?
C15 C16 1.4018(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.4045(18) . ?
C16 C19 1.4595(19) . ?
C17 C18 1.3852(19) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3503(18) . ?
C19 H19 0.9400 . ?
C20 C21 1.4441(19) . ?
C20 C22 1.4839(18) . ?
C22 C27 1.3991(18) . ?
C22 C23 1.4025(19) . ?
C23 C24 1.3797(19) . ?
C23 H23 0.9400 . ?
C24 C25 1.3835(19) . ?
C25 C26 1.385(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.383(2) . ?
C26 H26 0.9400 . ?
C27 H27 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 C1 N1 129.30(14) . . ?
C2 C1 C6 121.96(13) . . ?
N1 C1 C6 108.68(13) . . ?
C12 N1 C1 108.38(12) . . ?
C12 N1 C13 125.36(11) . . ?
C1 N1 C13 126.08(12) . . ?
C3 C2 C1 116.98(17) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C5 C4 C3 121.27(15) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C2 C3 C4 121.50(17) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C4 C5 C6 118.65(17) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.58(15) . . ?
C5 C6 C7 133.30(16) . . ?
C1 C6 C7 107.01(12) . . ?
C8 C7 C12 119.55(14) . . ?
C8 C7 C6 133.47(14) . . ?
C12 C7 C6 106.97(13) . . ?
C9 C8 C7 118.86(15) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.90(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.86(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.15(14) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
N1 C12 C11 129.32(13) . . ?
N1 C12 C7 108.91(12) . . ?
C11 C12 C7 121.67(13) . . ?
C18 C13 C14 119.71(12) . . ?
C18 C13 N1 120.23(11) . . ?
C14 C13 N1 120.06(11) . . ?
C15 C14 C13 120.03(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 121.22(12) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 117.87(12) . . ?
C15 C16 C19 124.06(12) . . ?
C17 C16 C19 118.07(12) . . ?
C18 C17 C16 121.13(12) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 119.95(11) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C16 129.28(12) . . ?
C20 C19 H19 115.4 . . ?
C16 C19 H19 115.4 . . ?
C19 C20 C21 119.55(13) . . ?
C19 C20 C22 125.10(12) . . ?
C21 C20 C22 115.23(11) . . ?
N2 C21 C20 177.62(14) . . ?
C27 C22 C23 118.36(13) . . ?
C27 C22 C20 120.36(12) . . ?
C23 C22 C20 121.28(11) . . ?
C24 C23 C22 119.51(12) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C23 C24 C25 122.30(13) . . ?
C23 C24 Cl1 119.17(10) . . ?
C25 C24 Cl1 118.52(11) . . ?
C24 C25 C26 118.14(13) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C27 C26 C25 120.86(13) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 120.82(13) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?

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 C1 N1 C12 177.24(14) . . . . ?
C6 C1 N1 C12 0.04(14) . . . . ?
C2 C1 N1 C13 1.9(2) . . . . ?
C6 C1 N1 C13 -175.35(12) . . . . ?
N1 C1 C2 C3 -174.43(14) . . . . ?
C6 C1 C2 C3 2.4(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C5 C4 C3 C2 -1.3(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C4 C5 C6 C7 175.76(16) . . . . ?
C2 C1 C6 C5 -2.3(2) . . . . ?
N1 C1 C6 C5 175.19(13) . . . . ?
C2 C1 C6 C7 -178.88(13) . . . . ?
N1 C1 C6 C7 -1.43(15) . . . . ?
C5 C6 C7 C8 7.4(3) . . . . ?
C1 C6 C7 C8 -176.63(15) . . . . ?
C5 C6 C7 C12 -173.70(16) . . . . ?
C1 C6 C7 C12 2.26(15) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
C6 C7 C8 C9 178.73(15) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C1 N1 C12 C11 177.79(13) . . . . ?
C13 N1 C12 C11 -6.8(2) . . . . ?
C1 N1 C12 C7 1.42(14) . . . . ?
C13 N1 C12 C7 176.85(12) . . . . ?
C10 C11 C12 N1 -176.11(13) . . . . ?
C10 C11 C12 C7 -0.15(19) . . . . ?
C8 C7 C12 N1 176.80(12) . . . . ?
C6 C7 C12 N1 -2.27(14) . . . . ?
C8 C7 C12 C11 0.1(2) . . . . ?
C6 C7 C12 C11 -178.97(12) . . . . ?
C12 N1 C13 C18 -45.15(19) . . . . ?
C1 N1 C13 C18 129.48(14) . . . . ?
C12 N1 C13 C14 133.68(14) . . . . ?
C1 N1 C13 C14 -51.70(19) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
N1 C13 C14 C15 -177.46(12) . . . . ?
C13 C14 C15 C16 1.4(2) . . . . ?
C14 C15 C16 C17 -3.4(2) . . . . ?
C14 C15 C16 C19 176.10(13) . . . . ?
C15 C16 C17 C18 2.7(2) . . . . ?
C19 C16 C17 C18 -176.85(13) . . . . ?
C16 C17 C18 C13 0.0(2) . . . . ?
C14 C13 C18 C17 -2.1(2) . . . . ?
N1 C13 C18 C17 176.75(12) . . . . ?
C15 C16 C19 C20 -27.7(2) . . . . ?
C17 C16 C19 C20 151.75(15) . . . . ?
C16 C19 C20 C21 -2.1(2) . . . . ?
C16 C19 C20 C22 -178.09(13) . . . . ?
C19 C20 C22 C27 -179.38(13) . . . . ?
C21 C20 C22 C27 4.52(18) . . . . ?
C19 C20 C22 C23 0.7(2) . . . . ?
C21 C20 C22 C23 -175.45(12) . . . . ?
C27 C22 C23 C24 -0.5(2) . . . . ?
C20 C22 C23 C24 179.51(12) . . . . ?
C22 C23 C24 C25 -0.5(2) . . . . ?
C22 C23 C24 Cl1 178.31(10) . . . . ?
C23 C24 C25 C26 0.8(2) . . . . ?
Cl1 C24 C25 C26 -178.09(12) . . . . ?
C24 C25 C26 C27 0.0(2) . . . . ?
C25 C26 C27 C22 -1.0(2) . . . . ?
C23 C22 C27 C26 1.2(2) . . . . ?
C20 C22 C27 C26 -178.75(14) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_SPA299
_database_code_depnum_ccdc_archive 'CCDC 1945304'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 Cl N2'
_chemical_formula_sum            'C27 H17 Cl N2'
_chemical_formula_weight         404.88

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'
Cl Cl 0.1230 0.1255 '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                   9.0860(18)
_cell_length_b                   13.597(3)
_cell_length_c                   16.250(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.35(3)
_cell_angle_gamma                90
_cell_volume                     1991.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    58159
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yello
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.054
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.958
_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            19243
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.737
_diffrn_reflns_theta_max         25.500
_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             5320
_reflns_number_gt                4118
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&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)+(0.1050P)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         5320
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1774
_refine_ls_wR_factor_gt          0.1695
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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 0.81127(14) 0.26270(8) 0.14116(7) 0.0364(3) Uani 1 1 d . . . . .
N2 N 0.8364(2) 0.73949(11) 0.26810(11) 0.0652(5) Uani 1 1 d . . . . .
C1 C 0.85869(17) 0.28225(10) 0.06443(8) 0.0363(3) Uani 1 1 d . . . . .
C2 C 0.8777(2) 0.37247(11) 0.02630(10) 0.0444(4) Uani 1 1 d . . . . .
H2 H 0.862569 0.432057 0.053332 0.053 Uiso 1 1 calc R U . . .
C3 C 0.9193(2) 0.37134(13) -0.05240(10) 0.0512(4) Uani 1 1 d . . . . .
H3 H 0.931600 0.431291 -0.079504 0.061 Uiso 1 1 calc R U . . .
C4 C 0.9437(2) 0.28301(13) -0.09291(10) 0.0504(4) Uani 1 1 d . . . . .
H4 H 0.974950 0.284384 -0.145861 0.061 Uiso 1 1 calc R U . . .
C5 C 0.92230(18) 0.19431(12) -0.05558(9) 0.0444(4) Uani 1 1 d . . . . .
H5 H 0.936895 0.135127 -0.083314 0.053 Uiso 1 1 calc R U . . .
C6 C 0.87867(17) 0.19265(10) 0.02382(9) 0.0373(3) Uani 1 1 d . . . . .
C7 C 0.84032(16) 0.11506(10) 0.07789(9) 0.0356(3) Uani 1 1 d . . . . .
C8 C 0.83331(17) 0.01256(10) 0.07099(9) 0.0408(3) Uani 1 1 d . . . . .
H8 H 0.856510 -0.018746 0.022710 0.049 Uiso 1 1 calc R U . . .
C9 C 0.79195(17) -0.04215(11) 0.13588(11) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.786626 -0.111037 0.131655 0.053 Uiso 1 1 calc R U . . .
C10 C 0.75785(17) 0.00456(11) 0.20802(10) 0.0427(3) Uani 1 1 d . . . . .
H10 H 0.732326 -0.033992 0.252079 0.051 Uiso 1 1 calc R U . . .
C11 C 0.76078(17) 0.10617(11) 0.21612(9) 0.0394(3) Uani 1 1 d . . . . .
H11 H 0.737061 0.136977 0.264509 0.047 Uiso 1 1 calc R U . . .
C12 C 0.80020(16) 0.16072(10) 0.14982(9) 0.0349(3) Uani 1 1 d . . . . .
C13 C 0.77383(16) 0.33476(10) 0.19797(8) 0.0336(3) Uani 1 1 d . . . . .
C14 C 0.87031(16) 0.41270(10) 0.21958(8) 0.0349(3) Uani 1 1 d . . . . .
H14 H 0.961392 0.415785 0.198010 0.042 Uiso 1 1 calc R U . . .
C15 C 0.83319(16) 0.48574(10) 0.27260(8) 0.0335(3) Uani 1 1 d . . . . .
H15 H 0.897853 0.539098 0.285417 0.040 Uiso 1 1 calc R U . . .
C16 C 0.69979(15) 0.48070(9) 0.30735(7) 0.0315(3) Uani 1 1 d . . . . .
C17 C 0.60736(16) 0.39924(10) 0.28786(9) 0.0355(3) Uani 1 1 d . . . . .
H17 H 0.520147 0.392917 0.312918 0.043 Uiso 1 1 calc R U . . .
C18 C 0.64149(16) 0.32794(10) 0.23261(9) 0.0364(3) Uani 1 1 d . . . . .
H18 H 0.576008 0.275309 0.218528 0.044 Uiso 1 1 calc R U . . .
C19 C 0.65487(15) 0.55432(10) 0.36494(8) 0.0327(3) Uani 1 1 d . . . . .
H19 H 0.593015 0.530923 0.402777 0.039 Uiso 1 1 calc R U . . .
C20 C 0.68889(15) 0.65027(10) 0.37175(8) 0.0332(3) Uani 1 1 d . . . . .
C21 C 0.77397(19) 0.69734(11) 0.31336(10) 0.0424(4) Uani 1 1 d . . . . .
Cl1A Cl 0.5057(4) 0.9074(6) 0.6401(3) 0.0690(10) Uani 0.500(16) 1 d . . P A 1
C22A C 0.64111(16) 0.71697(10) 0.43538(8) 0.0349(3) Uani 0.500(16) 1 d . . P A
1
C23A C 0.7212(9) 0.7962(7) 0.4633(6) 0.0507(17) Uani 0.500(16) 1 d . . P A 1
H23A H 0.807196 0.811470 0.439342 0.061 Uiso 0.500(16) 1 calc R U P A 1
C24A C 0.6821(9) 0.8558(7) 0.5255(7) 0.060(2) Uani 0.500(16) 1 d . . P A 1
H24A H 0.739104 0.911410 0.543023 0.072 Uiso 0.500(16) 1 calc R U P A 1
C25A C 0.5538(16) 0.8311(8) 0.5627(7) 0.0450(19) Uani 0.500(16) 1 d . . P A 1
C26A C 0.48477(19) 0.75478(13) 0.54120(10) 0.0469(4) Uani 0.500(16) 1 d . . P A
1
H26A H 0.400067 0.739095 0.566247 0.056 Uiso 0.500(16) 1 calc R U P A 1
C27A C 0.52761(17) 0.69174(11) 0.48170(9) 0.0407(3) Uani 0.500(16) 1 d . . P A
1
H27A H 0.479349 0.630857 0.472344 0.049 Uiso 0.500(16) 1 calc R U P A 1
Cl1B Cl 0.4999(5) 0.9378(5) 0.6188(5) 0.0790(10) Uani 0.500(16) 1 d . . P A 2
C22B C 0.64111(16) 0.71697(10) 0.43538(8) 0.0349(3) Uani 0.500(16) 1 d . . P A
2
C23B C 0.6934(11) 0.8185(7) 0.4370(6) 0.0534(18) Uani 0.500(16) 1 d . . P A 2
H23B H 0.756423 0.839613 0.398981 0.064 Uiso 0.500(16) 1 calc R U P A 2
C24B C 0.6498(11) 0.8839(7) 0.4949(7) 0.064(2) Uani 0.500(16) 1 d . . P A 2
H24B H 0.686581 0.948559 0.497369 0.077 Uiso 0.500(16) 1 calc R U P A 2
C25B C 0.5561(17) 0.8553(8) 0.5468(7) 0.047(2) Uani 0.500(16) 1 d . . P A 2
C26B C 0.48477(19) 0.75478(13) 0.54120(10) 0.0469(4) Uani 0.500(16) 1 d . . P A
2
H26B H 0.414997 0.736030 0.576245 0.056 Uiso 0.500(16) 1 calc R U P A 2
C27B C 0.52761(17) 0.69174(11) 0.48170(9) 0.0407(3) Uani 0.500(16) 1 d . . P A
2
H27B H 0.479349 0.630857 0.472344 0.049 Uiso 0.500(16) 1 calc R U P A 2


_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 C1 1.3958(18) . ?
N1 C12 1.3986(17) . ?
N1 C13 1.4172(16) . ?
N2 C21 1.139(2) . ?
C1 C2 1.395(2) . ?
C1 C6 1.4083(18) . ?
C2 C3 1.379(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.401(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.444(2) . ?
C7 C8 1.3989(19) . ?
C7 C12 1.4120(18) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.402(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.392(2) . ?
C11 H11 0.9400 . ?
C13 C14 1.391(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.3845(17) . ?
C14 H14 0.9400 . ?
C15 C16 1.4027(19) . ?
C15 H15 0.9400 . ?
C16 C17 1.402(2) . ?
C16 C19 1.4636(17) . ?
C17 C18 1.3833(19) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3420(19) . ?
C19 H19 0.9400 . ?
C20 C21 1.4475(19) . ?
C20 C22B 1.4816(18) . ?
C20 C22A 1.4816(18) . ?
Cl1A C25A 1.729(13) . ?
C22A C23A 1.345(8) . ?
C22A C27A 1.395(2) . ?
C23A C24A 1.377(11) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.420(14) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.239(13) . ?
C26A C27A 1.385(2) . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9400 . ?
Cl1B C25B 1.744(12) . ?
C22B C27B 1.395(2) . ?
C22B C23B 1.459(9) . ?
C23B C24B 1.387(11) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.331(13) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.510(11) . ?
C26B C27B 1.385(2) . ?
C26B H26B 0.9400 . ?
C27B H27B 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
C1 N1 C12 108.25(11) . . ?
C1 N1 C13 125.27(11) . . ?
C12 N1 C13 126.41(12) . . ?
C2 C1 N1 129.35(13) . . ?
C2 C1 C6 121.46(13) . . ?
N1 C1 C6 109.07(12) . . ?
C3 C2 C1 117.78(14) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.60(15) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.32(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.63(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.17(14) . . ?
C5 C6 C7 133.84(13) . . ?
C1 C6 C7 106.94(12) . . ?
C8 C7 C12 119.37(14) . . ?
C8 C7 C6 133.73(13) . . ?
C12 C7 C6 106.88(12) . . ?
C9 C8 C7 119.31(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.33(14) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 121.77(14) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.44(13) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 N1 129.43(12) . . ?
C11 C12 C7 121.71(13) . . ?
N1 C12 C7 108.85(12) . . ?
C14 C13 C18 119.79(12) . . ?
C14 C13 N1 119.67(12) . . ?
C18 C13 N1 120.54(13) . . ?
C15 C14 C13 120.50(13) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.48(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.13(12) . . ?
C17 C16 C19 118.48(12) . . ?
C15 C16 C19 123.36(12) . . ?
C18 C17 C16 121.53(13) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.46(13) . . ?
C17 C18 H18 120.3 . . ?
C13 C18 H18 120.3 . . ?
C20 C19 C16 129.61(12) . . ?
C20 C19 H19 115.2 . . ?
C16 C19 H19 115.2 . . ?
C19 C20 C21 120.83(12) . . ?
C19 C20 C22B 124.59(12) . . ?
C21 C20 C22B 114.56(12) . . ?
C19 C20 C22A 124.59(12) . . ?
C21 C20 C22A 114.56(12) . . ?
N2 C21 C20 175.85(17) . . ?
C23A C22A C27A 114.8(4) . . ?
C23A C22A C20 122.1(4) . . ?
C27A C22A C20 121.93(13) . . ?
C22A C23A C24A 122.7(6) . . ?
C22A C23A H23A 118.7 . . ?
C24A C23A H23A 118.7 . . ?
C23A C24A C25A 118.4(8) . . ?
C23A C24A H24A 120.8 . . ?
C25A C24A H24A 120.8 . . ?
C26A C25A C24A 119.4(10) . . ?
C26A C25A Cl1A 122.8(8) . . ?
C24A C25A Cl1A 117.7(8) . . ?
C25A C26A C27A 122.5(6) . . ?
C25A C26A H26A 118.7 . . ?
C27A C26A H26A 118.7 . . ?
C26A C27A C22A 121.18(15) . . ?
C26A C27A H27A 119.4 . . ?
C22A C27A H27A 119.4 . . ?
C27B C22B C23B 118.9(4) . . ?
C27B C22B C20 121.93(13) . . ?
C23B C22B C20 117.9(4) . . ?
C24B C23B C22B 119.9(6) . . ?
C24B C23B H23B 120.1 . . ?
C22B C23B H23B 120.1 . . ?
C25B C24B C23B 120.2(8) . . ?
C25B C24B H24B 119.9 . . ?
C23B C24B H24B 119.9 . . ?
C24B C25B C26B 122.1(9) . . ?
C24B C25B Cl1B 120.2(7) . . ?
C26B C25B Cl1B 117.5(7) . . ?
C27B C26B C25B 116.4(5) . . ?
C27B C26B H26B 121.8 . . ?
C25B C26B H26B 121.8 . . ?
C26B C27B C22B 121.18(15) . . ?
C26B C27B H27B 119.4 . . ?
C22B C27B H27B 119.4 . . ?

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
C12 N1 C1 C2 175.98(16) . . . . ?
C13 N1 C1 C2 -1.1(3) . . . . ?
C12 N1 C1 C6 -0.21(17) . . . . ?
C13 N1 C1 C6 -177.25(13) . . . . ?
N1 C1 C2 C3 -176.85(16) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 176.41(16) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
N1 C1 C6 C5 178.26(14) . . . . ?
C2 C1 C6 C7 -175.98(14) . . . . ?
N1 C1 C6 C7 0.57(16) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C1 C6 C7 C8 177.59(16) . . . . ?
C5 C6 C7 C12 -177.91(17) . . . . ?
C1 C6 C7 C12 -0.70(16) . . . . ?
C12 C7 C8 C9 -2.1(2) . . . . ?
C6 C7 C8 C9 179.76(16) . . . . ?
C7 C8 C9 C10 -0.2(2) . . . . ?
C8 C9 C10 C11 1.6(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 N1 179.62(15) . . . . ?
C10 C11 C12 C7 -1.9(2) . . . . ?
C1 N1 C12 C11 178.37(15) . . . . ?
C13 N1 C12 C11 -4.6(3) . . . . ?
C1 N1 C12 C7 -0.24(17) . . . . ?
C13 N1 C12 C7 176.75(13) . . . . ?
C8 C7 C12 C11 3.3(2) . . . . ?
C6 C7 C12 C11 -178.16(14) . . . . ?
C8 C7 C12 N1 -178.00(13) . . . . ?
C6 C7 C12 N1 0.58(16) . . . . ?
C1 N1 C13 C14 -49.4(2) . . . . ?
C12 N1 C13 C14 134.14(15) . . . . ?
C1 N1 C13 C18 130.91(16) . . . . ?
C12 N1 C13 C18 -45.6(2) . . . . ?
C18 C13 C14 C15 -2.6(2) . . . . ?
N1 C13 C14 C15 177.62(12) . . . . ?
C13 C14 C15 C16 2.0(2) . . . . ?
C14 C15 C16 C17 1.0(2) . . . . ?
C14 C15 C16 C19 178.88(12) . . . . ?
C15 C16 C17 C18 -3.4(2) . . . . ?
C19 C16 C17 C18 178.66(13) . . . . ?
C16 C17 C18 C13 2.7(2) . . . . ?
C14 C13 C18 C17 0.3(2) . . . . ?
N1 C13 C18 C17 -179.94(12) . . . . ?
C17 C16 C19 C20 -153.84(15) . . . . ?
C15 C16 C19 C20 28.3(2) . . . . ?
C16 C19 C20 C21 4.7(2) . . . . ?
C16 C19 C20 C22B -177.38(13) . . . . ?
C16 C19 C20 C22A -177.38(13) . . . . ?
C19 C20 C22A C23A 151.5(5) . . . . ?
C21 C20 C22A C23A -30.4(6) . . . . ?
C19 C20 C22A C27A -15.6(2) . . . . ?
C21 C20 C22A C27A 162.50(15) . . . . ?
C27A C22A C23A C24A -8.5(8) . . . . ?
C20 C22A C23A C24A -176.4(5) . . . . ?
C22A C23A C24A C25A 1.3(11) . . . . ?
C23A C24A C25A C26A 3.4(14) . . . . ?
C23A C24A C25A Cl1A -179.4(7) . . . . ?
C24A C25A C26A C27A -0.1(13) . . . . ?
Cl1A C25A C26A C27A -177.1(5) . . . . ?
C25A C26A C27A C22A -7.8(8) . . . . ?
C23A C22A C27A C26A 11.7(5) . . . . ?
C20 C22A C27A C26A 179.71(14) . . . . ?
C19 C20 C22B C27B -15.6(2) . . . . ?
C21 C20 C22B C27B 162.50(15) . . . . ?
C19 C20 C22B C23B 177.1(5) . . . . ?
C21 C20 C22B C23B -4.8(5) . . . . ?
C27B C22B C23B C24B 11.4(8) . . . . ?
C20 C22B C23B C24B 179.2(5) . . . . ?
C22B C23B C24B C25B -2.5(12) . . . . ?
C23B C24B C25B C26B -4.7(16) . . . . ?
C23B C24B C25B Cl1B -179.3(7) . . . . ?
C24B C25B C26B C27B 3.1(14) . . . . ?
Cl1B C25B C26B C27B 177.9(6) . . . . ?
C25B C26B C27B C22B 6.0(7) . . . . ?
C23B C22B C27B C26B -13.1(6) . . . . ?
C20 C22B C27B C26B 179.71(14) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_SPA209
_database_code_depnum_ccdc_archive 'CCDC 1945306'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H17 Br N2'
_chemical_formula_sum            'C27 H17 Br N2'
_chemical_formula_weight         449.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1086 1.8591 '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                   8.9710(18)
_cell_length_b                   13.595(3)
_cell_length_c                   16.421(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.70(3)
_cell_angle_gamma                90
_cell_volume                     1989.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    67696
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    1.340
_shelx_estimated_absorpt_T_min   0.842
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21085
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             5660
_reflns_number_gt                4593
_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-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0610P)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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0181(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5660
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.48670(2) 0.93706(2) 0.37111(2) 0.03631(9) Uani 1 1 d . . . . .
N1 N 0.18953(15) 0.25530(9) 0.85424(7) 0.0139(2) Uani 1 1 d . . . . .
N2 N 0.16329(19) 0.72931(11) 0.73651(10) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.14384(17) 0.27787(11) 0.93074(9) 0.0141(3) Uani 1 1 d . . . . .
C2 C 0.12814(18) 0.36951(11) 0.96692(9) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.144767 0.428620 0.938464 0.021 Uiso 1 1 calc R U . . .
C3 C 0.08750(19) 0.37147(12) 1.04569(10) 0.0205(3) Uani 1 1 d . . . . .
H3 H 0.076690 0.433029 1.071741 0.025 Uiso 1 1 calc R U . . .
C4 C 0.06196(19) 0.28445(12) 1.08784(9) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.031026 0.287775 1.141161 0.024 Uiso 1 1 calc R U . . .
C5 C 0.08155(18) 0.19377(12) 1.05224(9) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.066558 0.134967 1.081458 0.021 Uiso 1 1 calc R U . . .
C6 C 0.12349(17) 0.18940(11) 0.97309(9) 0.0146(3) Uani 1 1 d . . . . .
C7 C 0.16011(17) 0.11006(11) 0.92046(9) 0.0142(3) Uani 1 1 d . . . . .
C8 C 0.16645(17) 0.00751(11) 0.92925(10) 0.0161(3) Uani 1 1 d . . . . .
H8 H 0.143259 -0.022715 0.978394 0.019 Uiso 1 1 calc R U . . .
C9 C 0.20699(18) -0.04906(11) 0.86527(10) 0.0179(3) Uani 1 1 d . . . . .
H9 H 0.212247 -0.118565 0.870835 0.021 Uiso 1 1 calc R U . . .
C10 C 0.24042(17) -0.00496(11) 0.79231(10) 0.0168(3) Uani 1 1 d . . . . .
H10 H 0.265854 -0.045419 0.748828 0.020 Uiso 1 1 calc R U . . .
C11 C 0.23719(17) 0.09670(11) 0.78216(9) 0.0154(3) Uani 1 1 d . . . . .
H11 H 0.260009 0.126327 0.732705 0.018 Uiso 1 1 calc R U . . .
C12 C 0.19910(17) 0.15334(10) 0.84750(9) 0.0135(3) Uani 1 1 d . . . . .
C13 C 0.22625(17) 0.32613(10) 0.79646(8) 0.0123(3) Uani 1 1 d . . . . .
C14 C 0.36004(17) 0.31919(10) 0.76132(9) 0.0138(3) Uani 1 1 d . . . . .
H14 H 0.426894 0.265900 0.774793 0.017 Uiso 1 1 calc R U . . .
C15 C 0.39441(16) 0.39095(10) 0.70649(9) 0.0129(3) Uani 1 1 d . . . . .
H15 H 0.483122 0.384682 0.680473 0.015 Uiso 1 1 calc R U . . .
C16 C 0.30079(16) 0.47257(11) 0.68870(8) 0.0119(3) Uani 1 1 d . . . . .
C17 C 0.16556(16) 0.47706(11) 0.72298(9) 0.0126(3) Uani 1 1 d . . . . .
H17 H 0.099131 0.530742 0.710218 0.015 Uiso 1 1 calc R U . . .
C18 C 0.12763(17) 0.40377(11) 0.77548(9) 0.0132(3) Uani 1 1 d . . . . .
H18 H 0.034135 0.406425 0.797249 0.016 Uiso 1 1 calc R U . . .
C19 C 0.34630(17) 0.54787(10) 0.63267(9) 0.0129(3) Uani 1 1 d . . . . .
H19 H 0.409141 0.525915 0.593616 0.015 Uiso 1 1 calc R U . . .
C20 C 0.31058(16) 0.64417(11) 0.62936(8) 0.0128(3) Uani 1 1 d . . . . .
C21 C 0.22569(18) 0.68827(11) 0.68954(10) 0.0171(3) Uani 1 1 d . . . . .
C22 C 0.35561(16) 0.71390(10) 0.56734(9) 0.0133(3) Uani 1 1 d . . . . .
C23 C 0.2788(2) 0.80212(14) 0.55310(13) 0.0320(5) Uani 1 1 d . . . . .
H23 H 0.198359 0.817382 0.583805 0.038 Uiso 1 1 calc R U . . .
C24 C 0.3175(2) 0.86822(16) 0.49485(15) 0.0409(6) Uani 1 1 d . . . . .
H24 H 0.263864 0.928205 0.485579 0.049 Uiso 1 1 calc R U . . .
C25 C 0.43445(19) 0.84619(13) 0.45046(10) 0.0231(4) Uani 1 1 d . . . . .
C26 C 0.51448(18) 0.75960(12) 0.46354(9) 0.0170(3) Uani 1 1 d . . . . .
H26 H 0.595674 0.745373 0.433112 0.020 Uiso 1 1 calc R U . . .
C27 C 0.47430(17) 0.69371(11) 0.52188(9) 0.0156(3) Uani 1 1 d . . . . .
H27 H 0.528458 0.633906 0.531003 0.019 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
Br1 C25 1.8938(16) . ?
N1 C12 1.3939(19) . ?
N1 C1 1.4003(19) . ?
N1 C13 1.4173(17) . ?
N2 C21 1.149(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.412(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(2) . ?
C7 C8 1.402(2) . ?
C7 C12 1.415(2) . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(2) . ?
C16 C19 1.4658(19) . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.348(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.446(2) . ?
C20 C22 1.4815(19) . ?
C22 C23 1.389(2) . ?
C22 C27 1.397(2) . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C26 C27 1.389(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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 N1 C1 108.44(12) . . ?
C12 N1 C13 126.95(12) . . ?
C1 N1 C13 124.54(12) . . ?
C2 C1 N1 129.25(13) . . ?
C2 C1 C6 121.74(13) . . ?
N1 C1 C6 108.87(13) . . ?
C3 C2 C1 117.76(14) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.38(15) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.43(14) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.50(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.12(14) . . ?
C5 C6 C7 133.96(14) . . ?
C1 C6 C7 106.86(12) . . ?
C8 C7 C12 119.32(14) . . ?
C8 C7 C6 133.67(14) . . ?
C12 C7 C6 106.99(12) . . ?
C9 C8 C7 119.03(14) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.79(14) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.53(14) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 117.36(14) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
N1 C12 C11 129.26(13) . . ?
N1 C12 C7 108.83(13) . . ?
C11 C12 C7 121.91(13) . . ?
C14 C13 C18 120.06(13) . . ?
C14 C13 N1 120.64(13) . . ?
C18 C13 N1 119.29(13) . . ?
C15 C14 C13 119.24(13) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.28(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.55(13) . . ?
C17 C16 C19 122.75(13) . . ?
C15 C16 C19 118.66(13) . . ?
C18 C17 C16 120.47(14) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 120.21(14) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C16 128.43(14) . . ?
C20 C19 H19 115.8 . . ?
C16 C19 H19 115.8 . . ?
C19 C20 C21 121.12(13) . . ?
C19 C20 C22 124.53(13) . . ?
C21 C20 C22 114.33(13) . . ?
N2 C21 C20 175.25(17) . . ?
C23 C22 C27 118.28(14) . . ?
C23 C22 C20 119.89(14) . . ?
C27 C22 C20 121.83(13) . . ?
C24 C23 C22 121.10(16) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 119.44(17) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 121.09(15) . . ?
C24 C25 Br1 119.13(13) . . ?
C26 C25 Br1 119.77(13) . . ?
C25 C26 C27 118.96(15) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 H26 120.5 . . ?
C26 C27 C22 121.12(14) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?

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
C12 N1 C1 C2 175.46(16) . . . . ?
C13 N1 C1 C2 -1.7(3) . . . . ?
C12 N1 C1 C6 -0.23(17) . . . . ?
C13 N1 C1 C6 -177.37(13) . . . . ?
N1 C1 C2 C3 -176.96(16) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 2.0(3) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 176.29(16) . . . . ?
C2 C1 C6 C5 2.2(2) . . . . ?
N1 C1 C6 C5 178.30(14) . . . . ?
C2 C1 C6 C7 -175.38(14) . . . . ?
N1 C1 C6 C7 0.70(17) . . . . ?
C5 C6 C7 C8 0.4(3) . . . . ?
C1 C6 C7 C8 177.45(16) . . . . ?
C5 C6 C7 C12 -177.98(17) . . . . ?
C1 C6 C7 C12 -0.90(16) . . . . ?
C12 C7 C8 C9 -1.7(2) . . . . ?
C6 C7 C8 C9 -179.87(16) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 1.4(2) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C1 N1 C12 C11 178.69(15) . . . . ?
C13 N1 C12 C11 -4.3(3) . . . . ?
C1 N1 C12 C7 -0.34(17) . . . . ?
C13 N1 C12 C7 176.71(13) . . . . ?
C10 C11 C12 N1 178.98(15) . . . . ?
C10 C11 C12 C7 -2.1(2) . . . . ?
C8 C7 C12 N1 -177.86(13) . . . . ?
C6 C7 C12 N1 0.77(17) . . . . ?
C8 C7 C12 C11 3.0(2) . . . . ?
C6 C7 C12 C11 -178.35(14) . . . . ?
C12 N1 C13 C14 -46.8(2) . . . . ?
C1 N1 C13 C14 129.77(16) . . . . ?
C12 N1 C13 C18 133.77(16) . . . . ?
C1 N1 C13 C18 -49.6(2) . . . . ?
C18 C13 C14 C15 0.9(2) . . . . ?
N1 C13 C14 C15 -178.46(13) . . . . ?
C13 C14 C15 C16 3.0(2) . . . . ?
C14 C15 C16 C17 -4.5(2) . . . . ?
C14 C15 C16 C19 177.62(13) . . . . ?
C15 C16 C17 C18 2.0(2) . . . . ?
C19 C16 C17 C18 179.82(13) . . . . ?
C16 C17 C18 C13 1.8(2) . . . . ?
C14 C13 C18 C17 -3.4(2) . . . . ?
N1 C13 C18 C17 176.05(13) . . . . ?
C17 C16 C19 C20 29.1(2) . . . . ?
C15 C16 C19 C20 -153.16(16) . . . . ?
C16 C19 C20 C21 5.0(2) . . . . ?
C16 C19 C20 C22 -176.57(14) . . . . ?
C19 C20 C22 C23 160.66(17) . . . . ?
C21 C20 C22 C23 -20.8(2) . . . . ?
C19 C20 C22 C27 -19.2(2) . . . . ?
C21 C20 C22 C27 159.31(14) . . . . ?
C27 C22 C23 C24 0.6(3) . . . . ?
C20 C22 C23 C24 -179.3(2) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C23 C24 C25 Br1 -179.91(18) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
Br1 C25 C26 C27 -179.85(12) . . . . ?
C25 C26 C27 C22 -0.3(2) . . . . ?
C23 C22 C27 C26 -0.3(2) . . . . ?
C20 C22 C27 C26 179.56(14) . . . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.938
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_SPA403
_database_code_depnum_ccdc_archive 'CCDC 1945298'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 F N2'
_chemical_formula_sum            'C27 H17 F N2'
_chemical_formula_weight         388.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0124 0.0074 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   13.351(3)
_cell_length_b                   12.726(3)
_cell_length_c                   11.533(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1959.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    65413
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.062
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.953
_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     0.610
_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            19429
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5352
_reflns_number_gt                5200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.993

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_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          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²+0.0917P] 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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration RM
_refine_ls_number_reflns         5352
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
F1 F 0.79003(11) 0.30368(15) 0.90931(14) 0.0571(4) Uani 1 1 d . . . . .
N1 N 0.09075(10) 0.37490(12) 0.34613(13) 0.0248(3) Uani 1 1 d . . . . .
N2 N 0.41480(13) 0.43908(19) 0.82497(16) 0.0435(4) Uani 1 1 d . . . . .
C1 C 0.01191(10) 0.44506(13) 0.36574(13) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.00737(11) 0.53083(14) 0.44060(16) 0.0272(3) Uani 1 1 d . . . . .
H2 H 0.061497 0.548114 0.489112 0.033 Uiso 1 1 calc R U . . .
C3 C -0.08006(13) 0.58979(15) 0.44087(19) 0.0320(4) Uani 1 1 d . . . . .
H3 H -0.084975 0.648438 0.490084 0.038 Uiso 1 1 calc R U . . .
C4 C -0.16144(13) 0.56366(16) 0.36909(19) 0.0339(4) Uani 1 1 d . . . . .
H4 H -0.220121 0.604389 0.371806 0.041 Uiso 1 1 calc R U . . .
C5 C -0.15616(11) 0.47868(14) 0.29448(17) 0.0290(3) Uani 1 1 d . . . . .
H5 H -0.210733 0.461521 0.246583 0.035 Uiso 1 1 calc R U . . .
C006 C 0.06201(11) 0.30477(13) 0.25933(14) 0.0229(3) Uani 1 1 d . . . . .
C6 C -0.06832(11) 0.41862(12) 0.29140(14) 0.0224(3) Uani 1 1 d . . . . .
C7 C -0.03661(11) 0.32916(13) 0.22360(13) 0.0230(3) Uani 1 1 d . . . . .
C8 C -0.08237(13) 0.26829(15) 0.13798(14) 0.0284(3) Uani 1 1 d . . . . .
H8 H -0.147639 0.283885 0.112727 0.034 Uiso 1 1 calc R U . . .
C9 C -0.02993(15) 0.18429(16) 0.09068(15) 0.0335(4) Uani 1 1 d . . . . .
H9 H -0.059919 0.142873 0.032802 0.040 Uiso 1 1 calc R U . . .
C10 C 0.06676(16) 0.16087(15) 0.12827(17) 0.0336(4) Uani 1 1 d . . . . .
H10 H 0.100746 0.103605 0.095069 0.040 Uiso 1 1 calc R U . . .
C11 C 0.11426(13) 0.21975(14) 0.21334(16) 0.0293(3) Uani 1 1 d . . . . .
H11 H 0.179151 0.202890 0.238914 0.035 Uiso 1 1 calc R U . . .
C12 C 0.18729(11) 0.37947(12) 0.39711(14) 0.0225(3) Uani 1 1 d . . . . .
C13 C 0.19803(12) 0.37831(14) 0.51750(15) 0.0262(3) Uani 1 1 d . . . . .
H13 H 0.140976 0.376692 0.565235 0.031 Uiso 1 1 calc R U . . .
C14 C 0.29285(12) 0.37955(15) 0.56680(14) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.299576 0.380331 0.647925 0.032 Uiso 1 1 calc R U . . .
C15 C 0.37882(11) 0.37964(13) 0.49671(14) 0.0226(3) Uani 1 1 d . . . . .
C16 C 0.36639(12) 0.38152(13) 0.37602(14) 0.0244(3) Uani 1 1 d . . . . .
H16 H 0.423177 0.382188 0.327852 0.029 Uiso 1 1 calc R U . . .
C17 C 0.27137(12) 0.38242(13) 0.32629(14) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.264169 0.385016 0.245264 0.031 Uiso 1 1 calc R U . . .
C18 C 0.48214(12) 0.37489(14) 0.53839(14) 0.0249(3) Uani 1 1 d . . . . .
H18 H 0.529952 0.360259 0.480777 0.030 Uiso 1 1 calc R U . . .
C19 C 0.52047(12) 0.38807(14) 0.64617(14) 0.0241(3) Uani 1 1 d . . . . .
C20 C 0.45910(12) 0.41465(16) 0.74416(16) 0.0290(3) Uani 1 1 d . . . . .
C21 C 0.62949(12) 0.37930(13) 0.67178(16) 0.0253(3) Uani 1 1 d . . . . .
C22 C 0.66012(14) 0.34593(15) 0.78132(16) 0.0309(4) Uani 1 1 d . . . . .
H22 H 0.612861 0.330408 0.839254 0.037 Uiso 1 1 calc R U . . .
C23 C 0.76126(15) 0.33622(16) 0.80274(19) 0.0365(4) Uani 1 1 d . . . . .
C24 C 0.83410(14) 0.35827(18) 0.7217(2) 0.0400(5) Uani 1 1 d . . . . .
H24 H 0.902475 0.350751 0.739281 0.048 Uiso 1 1 calc R U . . .
C25 C 0.80279(14) 0.39197(19) 0.6133(2) 0.0390(4) Uani 1 1 d . . . . .
H25 H 0.850707 0.407092 0.555936 0.047 Uiso 1 1 calc R U . . .
C26 C 0.70176(13) 0.40369(17) 0.58813(18) 0.0333(4) Uani 1 1 d . . . . .
H26 H 0.681828 0.428070 0.514734 0.040 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
F1 C23 1.353(2) . ?
N1 C006 1.395(2) . ?
N1 C1 1.399(2) . ?
N1 C12 1.4179(19) . ?
N2 C20 1.147(3) . ?
C1 C2 1.393(2) . ?
C1 C6 1.4127(19) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9400 . ?
C006 C11 1.392(2) . ?
C006 C7 1.414(2) . ?
C6 C7 1.445(2) . ?
C7 C8 1.396(2) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 C17 1.389(2) . ?
C12 C13 1.396(2) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.404(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.402(2) . ?
C15 C18 1.462(2) . ?
C16 C17 1.392(2) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 C19 1.355(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.436(2) . ?
C19 C21 1.489(2) . ?
C21 C22 1.394(2) . ?
C21 C26 1.399(3) . ?
C22 C23 1.378(2) . ?
C22 H22 0.9400 . ?
C23 C24 1.378(3) . ?
C24 C25 1.387(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.388(2) . ?
C25 H25 0.9400 . ?
C26 H26 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
C006 N1 C1 108.51(12) . . ?
C006 N1 C12 125.02(13) . . ?
C1 N1 C12 126.22(13) . . ?
C2 C1 N1 129.28(14) . . ?
C2 C1 C6 121.99(14) . . ?
N1 C1 C6 108.69(13) . . ?
C3 C2 C1 117.49(15) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.39(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 120.78(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.01(15) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C11 C006 N1 129.25(15) . . ?
C11 C006 C7 121.74(15) . . ?
N1 C006 C7 108.95(14) . . ?
C5 C6 C1 119.32(15) . . ?
C5 C6 C7 133.58(15) . . ?
C1 C6 C7 107.10(13) . . ?
C8 C7 C006 119.46(16) . . ?
C8 C7 C6 133.79(15) . . ?
C006 C7 C6 106.75(13) . . ?
C9 C8 C7 118.96(16) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.59(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.84(17) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C006 117.38(17) . . ?
C10 C11 H11 121.3 . . ?
C006 C11 H11 121.3 . . ?
C17 C12 C13 120.15(14) . . ?
C17 C12 N1 119.48(14) . . ?
C13 C12 N1 120.36(15) . . ?
C14 C13 C12 120.07(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.66(15) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.35(14) . . ?
C16 C15 C18 116.03(14) . . ?
C14 C15 C18 125.60(15) . . ?
C17 C16 C15 121.13(14) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C12 C17 C16 119.61(15) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C15 130.77(15) . . ?
C19 C18 H18 114.6 . . ?
C15 C18 H18 114.6 . . ?
C18 C19 C20 122.38(15) . . ?
C18 C19 C21 122.82(15) . . ?
C20 C19 C21 114.77(15) . . ?
N2 C20 C19 176.0(2) . . ?
C22 C21 C26 119.34(16) . . ?
C22 C21 C19 119.29(16) . . ?
C26 C21 C19 121.37(15) . . ?
C23 C22 C21 118.50(18) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
F1 C23 C24 118.57(18) . . ?
F1 C23 C22 117.94(19) . . ?
C24 C23 C22 123.49(19) . . ?
C23 C24 C25 117.51(18) . . ?
C23 C24 H24 121.2 . . ?
C25 C24 H24 121.2 . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C21 120.16(19) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?

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
C006 N1 C1 C2 -177.24(17) . . . . ?
C12 N1 C1 C2 -2.8(3) . . . . ?
C006 N1 C1 C6 0.60(19) . . . . ?
C12 N1 C1 C6 175.05(16) . . . . ?
N1 C1 C2 C3 178.26(18) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C1 N1 C006 C11 -177.95(17) . . . . ?
C12 N1 C006 C11 7.5(3) . . . . ?
C1 N1 C006 C7 -0.67(19) . . . . ?
C12 N1 C006 C7 -175.21(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -177.87(18) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
N1 C1 C6 C5 -179.51(15) . . . . ?
C2 C1 C6 C7 177.73(15) . . . . ?
N1 C1 C6 C7 -0.30(18) . . . . ?
C11 C006 C7 C8 -1.6(2) . . . . ?
N1 C006 C7 C8 -179.11(15) . . . . ?
C11 C006 C7 C6 178.00(15) . . . . ?
N1 C006 C7 C6 0.47(18) . . . . ?
C5 C6 C7 C8 -1.6(3) . . . . ?
C1 C6 C7 C8 179.39(18) . . . . ?
C5 C6 C7 C006 178.94(18) . . . . ?
C1 C6 C7 C006 -0.11(17) . . . . ?
C006 C7 C8 C9 0.6(2) . . . . ?
C6 C7 C8 C9 -178.83(17) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C006 -0.8(3) . . . . ?
N1 C006 C11 C10 178.63(17) . . . . ?
C7 C006 C11 C10 1.7(3) . . . . ?
C006 N1 C12 C17 49.3(2) . . . . ?
C1 N1 C12 C17 -124.26(18) . . . . ?
C006 N1 C12 C13 -129.06(18) . . . . ?
C1 N1 C12 C13 57.4(2) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
N1 C12 C13 C14 178.02(15) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C16 1.8(3) . . . . ?
C13 C14 C15 C18 -176.33(17) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C18 C15 C16 C17 177.80(14) . . . . ?
C13 C12 C17 C16 1.6(2) . . . . ?
N1 C12 C17 C16 -176.75(15) . . . . ?
C15 C16 C17 C12 -1.2(3) . . . . ?
C16 C15 C18 C19 168.58(19) . . . . ?
C14 C15 C18 C19 -13.2(3) . . . . ?
C15 C18 C19 C20 -2.3(3) . . . . ?
C15 C18 C19 C21 179.55(17) . . . . ?
C18 C19 C21 C22 -150.74(18) . . . . ?
C20 C19 C21 C22 31.0(2) . . . . ?
C18 C19 C21 C26 29.1(3) . . . . ?
C20 C19 C21 C26 -149.14(19) . . . . ?
C26 C21 C22 C23 -1.2(3) . . . . ?
C19 C21 C22 C23 178.69(17) . . . . ?
C21 C22 C23 F1 -179.94(19) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
F1 C23 C24 C25 -179.7(2) . . . . ?
C22 C23 C24 C25 0.0(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C25 C26 C21 -1.4(3) . . . . ?
C22 C21 C26 C25 1.7(3) . . . . ?
C19 C21 C26 C25 -178.16(18) . . . . ?

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_SPA298
_database_code_depnum_ccdc_archive 'CCDC 1945299'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 F N2'
_chemical_formula_sum            'C27 H17 F N2'
_chemical_formula_weight         388.42

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'
F F 0.0134 0.0079 '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                   9.4000(19)
_cell_length_b                   13.351(3)
_cell_length_c                   15.562(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.44(3)
_cell_angle_gamma                90
_cell_volume                     1936.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    55418
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.961
_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            18743
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.788
_diffrn_reflns_theta_max         25.499
_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             5177
_reflns_number_gt                3986
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&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)+(0.0922P)²+0.1734P] 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         5177
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1636
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.80928(13) 0.72489(9) 0.13449(7) 0.0412(3) Uani 1 1 d . . . . .
N2 N 0.84577(19) 0.23733(11) 0.28734(10) 0.0651(4) Uani 1 1 d . . . . .
C1 C 0.86143(15) 0.70838(11) 0.05545(9) 0.0410(3) Uani 1 1 d . . . . .
C2 C 0.88320(18) 0.61865(12) 0.01382(10) 0.0479(4) Uani 1 1 d . . . . .
H2 H 0.867351 0.556693 0.039651 0.058 Uiso 1 1 calc R U . . .
C3 C 0.9290(2) 0.62384(13) -0.06704(10) 0.0551(4) Uani 1 1 d . . . . .
H3 H 0.943794 0.564144 -0.096678 0.066 Uiso 1 1 calc R U . . .
C4 C 0.95402(19) 0.71553(14) -0.10583(10) 0.0563(4) Uani 1 1 d . . . . .
H4 H 0.987649 0.716655 -0.160136 0.068 Uiso 1 1 calc R U . . .
C5 C 0.92968(17) 0.80409(12) -0.06503(9) 0.0481(4) Uani 1 1 d . . . . .
H5 H 0.944701 0.865690 -0.091685 0.058 Uiso 1 1 calc R U . . .
C6 C 0.88242(15) 0.80160(11) 0.01644(9) 0.0409(3) Uani 1 1 d . . . . .
C7 C 0.84037(14) 0.87776(11) 0.07342(9) 0.0405(3) Uani 1 1 d . . . . .
C8 C 0.83500(16) 0.98223(11) 0.06930(10) 0.0456(3) Uani 1 1 d . . . . .
H8 H 0.861065 1.016011 0.020698 0.055 Uiso 1 1 calc R U . . .
C9 C 0.79106(16) 1.03545(12) 0.13730(11) 0.0506(4) Uani 1 1 d . . . . .
H9 H 0.787314 1.105771 0.134925 0.061 Uiso 1 1 calc R U . . .
C10 C 0.75213(17) 0.98533(11) 0.20964(11) 0.0484(4) Uani 1 1 d . . . . .
H10 H 0.724753 1.022823 0.255928 0.058 Uiso 1 1 calc R U . . .
C11 C 0.75294(16) 0.88124(11) 0.21473(10) 0.0443(3) Uani 1 1 d . . . . .
H11 H 0.725003 0.847893 0.263048 0.053 Uiso 1 1 calc R U . . .
C12 C 0.79656(15) 0.82844(10) 0.14579(9) 0.0396(3) Uani 1 1 d . . . . .
C13 C 0.77132(15) 0.64965(10) 0.19147(8) 0.0386(3) Uani 1 1 d . . . . .
C14 C 0.86479(14) 0.57107(10) 0.21633(8) 0.0382(3) Uani 1 1 d . . . . .
H14 H 0.954254 0.568283 0.195550 0.046 Uiso 1 1 calc R U . . .
C15 C 0.82734(15) 0.49696(10) 0.27137(9) 0.0378(3) Uani 1 1 d . . . . .
H15 H 0.890295 0.443196 0.286265 0.045 Uiso 1 1 calc R U . . .
C16 C 0.69600(15) 0.50143(10) 0.30516(8) 0.0378(3) Uani 1 1 d . . . . .
C17 C 0.60554(15) 0.58284(11) 0.28140(10) 0.0434(3) Uani 1 1 d . . . . .
H17 H 0.518835 0.588500 0.305084 0.052 Uiso 1 1 calc R U . . .
C18 C 0.64025(15) 0.65493(11) 0.22419(10) 0.0442(3) Uani 1 1 d . . . . .
H18 H 0.575911 0.707361 0.207324 0.053 Uiso 1 1 calc R U . . .
C19 C 0.64981(15) 0.42993(10) 0.36733(9) 0.0396(3) Uani 1 1 d . . . . .
H19 H 0.584653 0.455818 0.402633 0.048 Uiso 1 1 calc R U . . .
C20 C 0.68535(14) 0.33318(10) 0.38222(8) 0.0367(3) Uani 1 1 d . . . . .
C21 C 0.77732(17) 0.28187(11) 0.32896(9) 0.0444(3) Uani 1 1 d . . . . .
F1A F 0.5042(8) 0.1171(7) 0.6540(4) 0.0866(19) Uani 0.492(14) 1 d . . P A 1
C23A C 0.7135(7) 0.1957(6) 0.4881(4) 0.0517(13) Uani 0.492(14) 1 d . . P A 1
H23A H 0.801221 0.180300 0.468267 0.062 Uiso 0.492(14) 1 calc R U P A 1
C24A C 0.6700(8) 0.1412(6) 0.5556(5) 0.070(2) Uani 0.492(14) 1 d . . P A 1
H24A H 0.722916 0.085569 0.578936 0.084 Uiso 0.492(14) 1 calc R U P A 1
C25A C 0.5462(9) 0.1708(6) 0.5876(5) 0.0534(14) Uani 0.492(14) 1 d . . P A 1
C22A C 0.63198(15) 0.27077(11) 0.45041(9) 0.0416(3) Uani 0.492(14) 1 d . . P A
1
C26A C 0.46852(17) 0.24314(14) 0.55615(10) 0.0530(4) Uani 0.492(14) 1 d . . P A
1
H26A H 0.379602 0.256640 0.575238 0.064 Uiso 0.492(14) 1 calc R U P A 1
C27A C 0.51830(16) 0.30124(12) 0.49322(10) 0.0461(3) Uani 0.492(14) 1 d . . P A
1
H27A H 0.474172 0.363241 0.478787 0.055 Uiso 0.492(14) 1 calc R U P A 1
F1B F 0.4612(7) 0.0775(6) 0.6204(6) 0.0950(19) Uani 0.508(14) 1 d . . P A 2
C22B C 0.63198(15) 0.27077(11) 0.45041(9) 0.0416(3) Uani 0.508(14) 1 d . . P A
2
C23B C 0.6708(9) 0.1642(5) 0.4561(7) 0.067(2) Uani 0.508(14) 1 d . . P A 2
H23B H 0.734235 0.138129 0.419823 0.081 Uiso 0.508(14) 1 calc R U P A 2
C24B C 0.6148(10) 0.1015(6) 0.5148(8) 0.089(3) Uani 0.508(14) 1 d . . P A 2
H24B H 0.643829 0.034191 0.520089 0.107 Uiso 0.508(14) 1 calc R U P A 2
C25B C 0.5185(9) 0.1379(6) 0.5640(6) 0.0626(18) Uani 0.508(14) 1 d . . P A 2
C26B C 0.46852(17) 0.24314(14) 0.55615(10) 0.0530(4) Uani 0.508(14) 1 d . . P A
2
H26B H 0.405391 0.269230 0.592664 0.064 Uiso 0.508(14) 1 calc R U P A 2
C27B C 0.51830(16) 0.30124(12) 0.49322(10) 0.0461(3) Uani 0.508(14) 1 d . . P A
2
H27B H 0.474172 0.363241 0.478787 0.055 Uiso 0.508(14) 1 calc R U P A 2


_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 C1 1.3993(18) . ?
N1 C12 1.4006(18) . ?
N1 C13 1.4158(17) . ?
N2 C21 1.138(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.4097(19) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.438(2) . ?
C7 C8 1.397(2) . ?
C7 C12 1.4112(19) . ?
C8 C9 1.381(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.399(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.392(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9400 . ?
C13 C14 1.3908(19) . ?
C13 C18 1.3945(19) . ?
C14 C15 1.3838(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.4044(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.3998(19) . ?
C16 C19 1.4644(18) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3468(19) . ?
C19 H19 0.9400 . ?
C20 C21 1.4455(19) . ?
C20 C22B 1.4865(18) . ?
C20 C22A 1.4865(18) . ?
F1A C25A 1.358(8) . ?
C23A C22A 1.349(5) . ?
C23A C24A 1.383(7) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.382(9) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.270(8) . ?
C22A C27A 1.3912(19) . ?
C26A C27A 1.378(2) . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9400 . ?
F1B C25B 1.354(8) . ?
C22B C27B 1.3912(19) . ?
C22B C23B 1.468(6) . ?
C23B C24B 1.391(7) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.349(10) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.482(8) . ?
C26B C27B 1.378(2) . ?
C26B H26B 0.9400 . ?
C27B H27B 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
C1 N1 C12 108.13(11) . . ?
C1 N1 C13 125.74(11) . . ?
C12 N1 C13 126.10(11) . . ?
C2 C1 N1 129.43(13) . . ?
C2 C1 C6 121.53(13) . . ?
N1 C1 C6 108.90(12) . . ?
C3 C2 C1 117.58(14) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.73(15) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.41(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.34(14) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.37(14) . . ?
C5 C6 C7 133.47(13) . . ?
C1 C6 C7 107.09(12) . . ?
C8 C7 C12 119.34(14) . . ?
C8 C7 C6 133.56(13) . . ?
C12 C7 C6 107.10(12) . . ?
C9 C8 C7 119.41(14) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.38(14) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 121.57(15) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 117.56(14) . . ?
C12 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C11 C12 N1 129.52(13) . . ?
C11 C12 C7 121.69(13) . . ?
N1 C12 C7 108.78(12) . . ?
C14 C13 C18 119.52(12) . . ?
C14 C13 N1 120.54(12) . . ?
C18 C13 N1 119.94(13) . . ?
C15 C14 C13 120.63(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.52(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 117.87(12) . . ?
C17 C16 C19 117.30(12) . . ?
C15 C16 C19 124.74(12) . . ?
C18 C17 C16 121.74(12) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C13 119.65(13) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C20 C19 C16 130.60(12) . . ?
C20 C19 H19 114.7 . . ?
C16 C19 H19 114.7 . . ?
C19 C20 C21 120.62(12) . . ?
C19 C20 C22B 124.15(12) . . ?
C21 C20 C22B 115.20(12) . . ?
C19 C20 C22A 124.15(12) . . ?
C21 C20 C22A 115.20(12) . . ?
N2 C21 C20 176.62(16) . . ?
C22A C23A C24A 121.0(4) . . ?
C22A C23A H23A 119.5 . . ?
C24A C23A H23A 119.5 . . ?
C25A C24A C23A 117.9(5) . . ?
C25A C24A H24A 121.0 . . ?
C23A C24A H24A 121.0 . . ?
C26A C25A F1A 119.1(6) . . ?
C26A C25A C24A 123.2(5) . . ?
F1A C25A C24A 117.7(6) . . ?
C23A C22A C27A 115.9(2) . . ?
C23A C22A C20 120.1(3) . . ?
C27A C22A C20 121.94(13) . . ?
C25A C26A C27A 118.1(3) . . ?
C25A C26A H26A 121.0 . . ?
C27A C26A H26A 121.0 . . ?
C26A C27A C22A 121.89(15) . . ?
C26A C27A H27A 119.1 . . ?
C22A C27A H27A 119.1 . . ?
C27B C22B C23B 117.0(2) . . ?
C27B C22B C20 121.94(13) . . ?
C23B C22B C20 118.8(3) . . ?
C24B C23B C22B 120.7(5) . . ?
C24B C23B H23B 119.6 . . ?
C22B C23B H23B 119.6 . . ?
C25B C24B C23B 119.6(5) . . ?
C25B C24B H24B 120.2 . . ?
C23B C24B H24B 120.2 . . ?
C24B C25B F1B 120.4(6) . . ?
C24B C25B C26B 121.6(5) . . ?
F1B C25B C26B 118.0(6) . . ?
C27B C26B C25B 117.3(3) . . ?
C27B C26B H26B 121.3 . . ?
C25B C26B H26B 121.3 . . ?
C26B C27B C22B 121.89(15) . . ?
C26B C27B H27B 119.1 . . ?
C22B C27B H27B 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
C12 N1 C1 C2 -175.59(15) . . . . ?
C13 N1 C1 C2 2.4(2) . . . . ?
C12 N1 C1 C6 0.19(16) . . . . ?
C13 N1 C1 C6 178.15(12) . . . . ?
N1 C1 C2 C3 176.51(15) . . . . ?
C6 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -176.09(15) . . . . ?
C2 C1 C6 C5 -1.6(2) . . . . ?
N1 C1 C6 C5 -177.82(13) . . . . ?
C2 C1 C6 C7 175.68(13) . . . . ?
N1 C1 C6 C7 -0.50(16) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C1 C6 C7 C8 -178.83(15) . . . . ?
C5 C6 C7 C12 177.40(16) . . . . ?
C1 C6 C7 C12 0.62(15) . . . . ?
C12 C7 C8 C9 1.9(2) . . . . ?
C6 C7 C8 C9 -178.67(15) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -1.6(2) . . . . ?
C9 C10 C11 C12 1.2(2) . . . . ?
C10 C11 C12 N1 179.10(15) . . . . ?
C10 C11 C12 C7 0.8(2) . . . . ?
C1 N1 C12 C11 -178.28(14) . . . . ?
C13 N1 C12 C11 3.8(2) . . . . ?
C1 N1 C12 C7 0.21(16) . . . . ?
C13 N1 C12 C7 -177.75(12) . . . . ?
C8 C7 C12 C11 -2.3(2) . . . . ?
C6 C7 C12 C11 178.12(13) . . . . ?
C8 C7 C12 N1 179.03(13) . . . . ?
C6 C7 C12 N1 -0.51(15) . . . . ?
C1 N1 C13 C14 49.8(2) . . . . ?
C12 N1 C13 C14 -132.64(15) . . . . ?
C1 N1 C13 C18 -131.28(16) . . . . ?
C12 N1 C13 C18 46.3(2) . . . . ?
C18 C13 C14 C15 1.6(2) . . . . ?
N1 C13 C14 C15 -179.40(12) . . . . ?
C13 C14 C15 C16 -1.9(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C14 C15 C16 C19 -176.58(13) . . . . ?
C15 C16 C17 C18 2.4(2) . . . . ?
C19 C16 C17 C18 179.17(13) . . . . ?
C16 C17 C18 C13 -2.7(2) . . . . ?
C14 C13 C18 C17 0.6(2) . . . . ?
N1 C13 C18 C17 -178.32(13) . . . . ?
C17 C16 C19 C20 156.83(15) . . . . ?
C15 C16 C19 C20 -26.6(2) . . . . ?
C16 C19 C20 C21 -4.0(2) . . . . ?
C16 C19 C20 C22B 178.01(13) . . . . ?
C16 C19 C20 C22A 178.01(13) . . . . ?
C22A C23A C24A C25A -5.0(8) . . . . ?
C23A C24A C25A C26A 2.6(9) . . . . ?
C23A C24A C25A F1A -179.8(5) . . . . ?
C24A C23A C22A C27A 11.5(6) . . . . ?
C24A C23A C22A C20 175.7(4) . . . . ?
C19 C20 C22A C23A -150.0(4) . . . . ?
C21 C20 C22A C23A 31.9(5) . . . . ?
C19 C20 C22A C27A 13.2(2) . . . . ?
C21 C20 C22A C27A -164.92(15) . . . . ?
F1A C25A C26A C27A 175.3(4) . . . . ?
C24A C25A C26A C27A -7.2(7) . . . . ?
C25A C26A C27A C22A 14.4(5) . . . . ?
C23A C22A C27A C26A -16.4(5) . . . . ?
C20 C22A C27A C26A 179.72(14) . . . . ?
C19 C20 C22B C27B 13.2(2) . . . . ?
C21 C20 C22B C27B -164.92(15) . . . . ?
C19 C20 C22B C23B 175.8(5) . . . . ?
C21 C20 C22B C23B -2.3(6) . . . . ?
C27B C22B C23B C24B -11.8(8) . . . . ?
C20 C22B C23B C24B -175.3(5) . . . . ?
C22B C23B C24B C25B 3.2(10) . . . . ?
C23B C24B C25B F1B 179.0(6) . . . . ?
C23B C24B C25B C26B 1.1(10) . . . . ?
C24B C25B C26B C27B 3.5(8) . . . . ?
F1B C25B C26B C27B -174.5(4) . . . . ?
C25B C26B C27B C22B -12.8(5) . . . . ?
C23B C22B C27B C26B 16.8(6) . . . . ?
C20 C22B C27B C26B 179.72(14) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_SPA300
_database_code_depnum_ccdc_archive 'CCDC 1945303'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 Cl N2'
_chemical_formula_sum            'C27 H17 Cl N2'
_chemical_formula_weight         404.88

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'
Cl Cl 0.1230 0.1255 '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                   9.0810(18)
_cell_length_b                   13.600(3)
_cell_length_c                   16.245(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.35(3)
_cell_angle_gamma                90
_cell_volume                     1989.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    60617
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.956
_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            19365
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.737
_diffrn_reflns_theta_max         25.498
_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             5317
_reflns_number_gt                4289
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&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)+(0.0978P)²+0.2303P] 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         5317
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1734
_refine_ls_wR_factor_gt          0.1660
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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 0.81091(14) 0.73724(8) 0.14112(7) 0.0360(3) Uani 1 1 d . . . . .
N2 N 0.8364(2) 0.26049(12) 0.26814(11) 0.0645(5) Uani 1 1 d . . . . .
C1 C 0.85880(16) 0.71781(11) 0.06439(9) 0.0368(3) Uani 1 1 d . . . . .
C2 C 0.87725(19) 0.62755(12) 0.02633(10) 0.0437(4) Uani 1 1 d . . . . .
H2 H 0.861540 0.568004 0.053272 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9196(2) 0.62878(13) -0.05261(10) 0.0502(4) Uani 1 1 d . . . . .
H3 H 0.932272 0.568894 -0.079717 0.060 Uiso 1 1 calc R U . . .
C4 C 0.9439(2) 0.71715(14) -0.09293(10) 0.0507(4) Uani 1 1 d . . . . .
H4 H 0.975161 0.715879 -0.145882 0.061 Uiso 1 1 calc R U . . .
C5 C 0.92224(18) 0.80571(12) -0.05565(9) 0.0438(4) Uani 1 1 d . . . . .
H5 H 0.936659 0.864896 -0.083415 0.053 Uiso 1 1 calc R U . . .
C6 C 0.87868(16) 0.80737(11) 0.02384(9) 0.0370(3) Uani 1 1 d . . . . .
C7 C 0.84013(16) 0.88480(10) 0.07772(9) 0.0355(3) Uani 1 1 d . . . . .
C8 C 0.83321(16) 0.98747(11) 0.07094(10) 0.0397(3) Uani 1 1 d . . . . .
H8 H 0.856509 1.018844 0.022694 0.048 Uiso 1 1 calc R U . . .
C9 C 0.79186(17) 1.04203(11) 0.13582(11) 0.0442(4) Uani 1 1 d . . . . .
H9 H 0.786373 1.110896 0.131522 0.053 Uiso 1 1 calc R U . . .
C10 C 0.75794(17) 0.99553(11) 0.20817(10) 0.0421(3) Uani 1 1 d . . . . .
H10 H 0.732666 1.034040 0.252321 0.050 Uiso 1 1 calc R U . . .
C11 C 0.76091(17) 0.89373(11) 0.21596(10) 0.0386(3) Uani 1 1 d . . . . .
H11 H 0.737258 0.862812 0.264333 0.046 Uiso 1 1 calc R U . . .
C12 C 0.80011(15) 0.83923(10) 0.14963(9) 0.0343(3) Uani 1 1 d . . . . .
C13 C 0.77381(15) 0.66534(10) 0.19796(8) 0.0329(3) Uani 1 1 d . . . . .
C14 C 0.87038(15) 0.58721(10) 0.21954(9) 0.0344(3) Uani 1 1 d . . . . .
H14 H 0.961393 0.583986 0.197853 0.041 Uiso 1 1 calc R U . . .
C15 C 0.83325(15) 0.51439(10) 0.27263(8) 0.0326(3) Uani 1 1 d . . . . .
H15 H 0.898185 0.461197 0.285592 0.039 Uiso 1 1 calc R U . . .
C16 C 0.69956(15) 0.51907(10) 0.30738(8) 0.0309(3) Uani 1 1 d . . . . .
C17 C 0.60733(15) 0.60087(10) 0.28791(9) 0.0352(3) Uani 1 1 d . . . . .
H17 H 0.520163 0.607390 0.313020 0.042 Uiso 1 1 calc R U . . .
C18 C 0.64158(16) 0.67186(10) 0.23282(9) 0.0359(3) Uani 1 1 d . . . . .
H18 H 0.576028 0.724482 0.218815 0.043 Uiso 1 1 calc R U . . .
C19 C 0.65462(15) 0.44586(10) 0.36499(8) 0.0328(3) Uani 1 1 d . . . . .
H19 H 0.592742 0.469292 0.402828 0.039 Uiso 1 1 calc R U . . .
C20 C 0.68896(15) 0.34970(10) 0.37176(8) 0.0320(3) Uani 1 1 d . . . . .
C21 C 0.77427(18) 0.30261(11) 0.31342(10) 0.0420(3) Uani 1 1 d . . . . .
Cl1A Cl 0.4979(5) 0.0607(5) 0.6179(5) 0.0770(10) Uani 0.467(16) 1 d . . P A 1
C22A C 0.64110(15) 0.28292(11) 0.43545(8) 0.0344(3) Uani 0.467(16) 1 d . . P A
1
C23A C 0.6919(11) 0.1800(6) 0.4369(6) 0.0502(17) Uani 0.467(16) 1 d . . P A 1
H23A H 0.755022 0.158865 0.398865 0.060 Uiso 0.467(16) 1 calc R U P A 1
C24A C 0.6480(11) 0.1148(7) 0.4931(6) 0.0607(19) Uani 0.467(16) 1 d . . P A 1
H24A H 0.684021 0.049948 0.494547 0.073 Uiso 0.467(16) 1 calc R U P A 1
C25A C 0.5534(15) 0.1427(8) 0.5468(8) 0.045(2) Uani 0.467(16) 1 d . . P A 1
C26A C 0.48465(18) 0.24525(14) 0.54122(10) 0.0463(4) Uani 0.467(16) 1 d . . P A
1
H26A H 0.416091 0.264859 0.576739 0.056 Uiso 0.467(16) 1 calc R U P A 1
C27A C 0.52746(17) 0.30822(11) 0.48168(9) 0.0404(3) Uani 0.467(16) 1 d . . P A
1
H27A H 0.479133 0.369064 0.472244 0.049 Uiso 0.467(16) 1 calc R U P A 1
Cl1B Cl 0.5066(4) 0.0917(5) 0.6396(3) 0.0689(9) Uani 0.533(16) 1 d . . P A 2
C22B C 0.64110(15) 0.28292(11) 0.43545(8) 0.0344(3) Uani 0.533(16) 1 d . . P A
2
C23B C 0.7211(8) 0.2041(6) 0.4621(6) 0.0503(16) Uani 0.533(16) 1 d . . P A 2
H23B H 0.807247 0.189142 0.438050 0.060 Uiso 0.533(16) 1 calc R U P A 2
C24B C 0.6806(8) 0.1433(6) 0.5245(6) 0.062(2) Uani 0.533(16) 1 d . . P A 2
H24B H 0.735683 0.086488 0.540882 0.074 Uiso 0.533(16) 1 calc R U P A 2
C25B C 0.5565(12) 0.1689(7) 0.5618(7) 0.0424(16) Uani 0.533(16) 1 d . . P A 2
C26B C 0.48465(18) 0.24525(14) 0.54122(10) 0.0463(4) Uani 0.533(16) 1 d . . P A
2
H26B H 0.400014 0.260222 0.566620 0.056 Uiso 0.533(16) 1 calc R U P A 2
C27B C 0.52746(17) 0.30822(11) 0.48168(9) 0.0404(3) Uani 0.533(16) 1 d . . P A
2
H27B H 0.479133 0.369064 0.472244 0.049 Uiso 0.533(16) 1 calc R U P A 2


_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 C1 1.3968(18) . ?
N1 C12 1.3987(17) . ?
N1 C13 1.4148(17) . ?
N2 C21 1.137(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.4073(19) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.374(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.441(2) . ?
C7 C8 1.401(2) . ?
C7 C12 1.4104(19) . ?
C8 C9 1.380(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.403(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9400 . ?
C13 C14 1.3936(19) . ?
C13 C18 1.394(2) . ?
C14 C15 1.3832(18) . ?
C14 H14 0.9400 . ?
C15 C16 1.4043(18) . ?
C15 H15 0.9400 . ?
C16 C17 1.4041(19) . ?
C16 C19 1.4598(18) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3457(19) . ?
C19 H19 0.9400 . ?
C20 C21 1.448(2) . ?
C20 C22B 1.4829(18) . ?
C20 C22A 1.4829(18) . ?
Cl1A C25A 1.725(13) . ?
C22A C27A 1.395(2) . ?
C22A C23A 1.473(8) . ?
C23A C24A 1.368(12) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.355(15) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.526(11) . ?
C26A C27A 1.384(2) . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9400 . ?
Cl1B C25B 1.747(11) . ?
C22B C23B 1.336(7) . ?
C22B C27B 1.395(2) . ?
C23B C24B 1.393(9) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.391(12) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.249(11) . ?
C26B C27B 1.384(2) . ?
C26B H26B 0.9400 . ?
C27B H27B 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
C1 N1 C12 108.03(11) . . ?
C1 N1 C13 125.38(12) . . ?
C12 N1 C13 126.54(12) . . ?
C2 C1 N1 129.13(13) . . ?
C2 C1 C6 121.64(13) . . ?
N1 C1 C6 109.10(12) . . ?
C3 C2 C1 117.60(14) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.51(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.43(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.65(14) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.13(14) . . ?
C5 C6 C7 133.80(14) . . ?
C1 C6 C7 107.01(12) . . ?
C8 C7 C12 119.29(14) . . ?
C8 C7 C6 133.82(13) . . ?
C12 C7 C6 106.88(12) . . ?
C9 C8 C7 119.32(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.52(14) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 121.42(15) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 117.64(14) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
C11 C12 N1 129.27(13) . . ?
C11 C12 C7 121.74(13) . . ?
N1 C12 C7 108.98(13) . . ?
C14 C13 C18 119.55(12) . . ?
C14 C13 N1 119.76(12) . . ?
C18 C13 N1 120.69(13) . . ?
C15 C14 C13 120.46(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.70(12) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 117.82(12) . . ?
C17 C16 C19 118.50(12) . . ?
C15 C16 C19 123.63(12) . . ?
C18 C17 C16 121.57(13) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.77(13) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 C16 129.37(12) . . ?
C20 C19 H19 115.3 . . ?
C16 C19 H19 115.3 . . ?
C19 C20 C21 120.93(12) . . ?
C19 C20 C22B 124.52(12) . . ?
C21 C20 C22B 114.52(12) . . ?
C19 C20 C22A 124.52(12) . . ?
C21 C20 C22A 114.52(12) . . ?
N2 C21 C20 175.76(17) . . ?
C27A C22A C23A 118.5(4) . . ?
C27A C22A C20 121.84(13) . . ?
C23A C22A C20 118.3(4) . . ?
C24A C23A C22A 120.6(7) . . ?
C24A C23A H23A 119.7 . . ?
C22A C23A H23A 119.7 . . ?
C25A C24A C23A 120.8(8) . . ?
C25A C24A H24A 119.6 . . ?
C23A C24A H24A 119.6 . . ?
C24A C25A C26A 120.4(9) . . ?
C24A C25A Cl1A 120.9(7) . . ?
C26A C25A Cl1A 118.6(8) . . ?
C27A C26A C25A 117.3(5) . . ?
C27A C26A H26A 121.4 . . ?
C25A C26A H26A 121.4 . . ?
C26A C27A C22A 121.12(15) . . ?
C26A C27A H27A 119.4 . . ?
C22A C27A H27A 119.4 . . ?
C23B C22B C27B 115.6(3) . . ?
C23B C22B C20 121.5(3) . . ?
C27B C22B C20 121.84(13) . . ?
C22B C23B C24B 121.9(6) . . ?
C22B C23B H23B 119.0 . . ?
C24B C23B H23B 119.0 . . ?
C25B C24B C23B 118.2(7) . . ?
C25B C24B H24B 120.9 . . ?
C23B C24B H24B 120.9 . . ?
C26B C25B C24B 121.1(8) . . ?
C26B C25B Cl1B 121.2(7) . . ?
C24B C25B Cl1B 117.7(7) . . ?
C25B C26B C27B 121.2(5) . . ?
C25B C26B H26B 119.4 . . ?
C27B C26B H26B 119.4 . . ?
C26B C27B C22B 121.12(15) . . ?
C26B C27B H27B 119.4 . . ?
C22B C27B H27B 119.4 . . ?

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
C12 N1 C1 C2 -175.77(16) . . . . ?
C13 N1 C1 C2 1.6(3) . . . . ?
C12 N1 C1 C6 0.02(16) . . . . ?
C13 N1 C1 C6 177.43(13) . . . . ?
N1 C1 C2 C3 176.83(16) . . . . ?
C6 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -176.33(16) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
N1 C1 C6 C5 -178.06(14) . . . . ?
C2 C1 C6 C7 175.67(14) . . . . ?
N1 C1 C6 C7 -0.50(16) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C1 C6 C7 C8 -177.77(16) . . . . ?
C5 C6 C7 C12 177.83(16) . . . . ?
C1 C6 C7 C12 0.78(15) . . . . ?
C12 C7 C8 C9 2.0(2) . . . . ?
C6 C7 C8 C9 -179.60(15) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 N1 -179.62(15) . . . . ?
C10 C11 C12 C7 1.9(2) . . . . ?
C1 N1 C12 C11 -178.14(14) . . . . ?
C13 N1 C12 C11 4.5(2) . . . . ?
C1 N1 C12 C7 0.48(16) . . . . ?
C13 N1 C12 C7 -176.89(13) . . . . ?
C8 C7 C12 C11 -3.2(2) . . . . ?
C6 C7 C12 C11 177.96(13) . . . . ?
C8 C7 C12 N1 178.02(13) . . . . ?
C6 C7 C12 N1 -0.77(16) . . . . ?
C1 N1 C13 C14 48.9(2) . . . . ?
C12 N1 C13 C14 -134.13(15) . . . . ?
C1 N1 C13 C18 -131.16(16) . . . . ?
C12 N1 C13 C18 45.8(2) . . . . ?
C18 C13 C14 C15 2.5(2) . . . . ?
N1 C13 C14 C15 -177.61(12) . . . . ?
C13 C14 C15 C16 -1.6(2) . . . . ?
C14 C15 C16 C17 -1.42(19) . . . . ?
C14 C15 C16 C19 -178.83(13) . . . . ?
C15 C16 C17 C18 3.7(2) . . . . ?
C19 C16 C17 C18 -178.79(13) . . . . ?
C16 C17 C18 C13 -2.8(2) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
N1 C13 C18 C17 179.81(13) . . . . ?
C17 C16 C19 C20 154.09(15) . . . . ?
C15 C16 C19 C20 -28.5(2) . . . . ?
C16 C19 C20 C21 -4.6(2) . . . . ?
C16 C19 C20 C22B 177.45(13) . . . . ?
C16 C19 C20 C22A 177.45(13) . . . . ?
C19 C20 C22A C27A 15.5(2) . . . . ?
C21 C20 C22A C27A -162.54(15) . . . . ?
C19 C20 C22A C23A -177.9(5) . . . . ?
C21 C20 C22A C23A 4.0(5) . . . . ?
C27A C22A C23A C24A -11.4(8) . . . . ?
C20 C22A C23A C24A -178.4(5) . . . . ?
C22A C23A C24A C25A 2.1(12) . . . . ?
C23A C24A C25A C26A 4.6(14) . . . . ?
C23A C24A C25A Cl1A -179.9(7) . . . . ?
C24A C25A C26A C27A -2.3(12) . . . . ?
Cl1A C25A C26A C27A -177.8(5) . . . . ?
C25A C26A C27A C22A -7.2(6) . . . . ?
C23A C22A C27A C26A 13.8(5) . . . . ?
C20 C22A C27A C26A -179.65(14) . . . . ?
C19 C20 C22B C23B -152.2(5) . . . . ?
C21 C20 C22B C23B 29.7(6) . . . . ?
C19 C20 C22B C27B 15.5(2) . . . . ?
C21 C20 C22B C27B -162.54(15) . . . . ?
C27B C22B C23B C24B 8.7(7) . . . . ?
C20 C22B C23B C24B 177.1(4) . . . . ?
C22B C23B C24B C25B -2.7(9) . . . . ?
C23B C24B C25B C26B -1.3(11) . . . . ?
C23B C24B C25B Cl1B 179.7(5) . . . . ?
C24B C25B C26B C27B -1.3(10) . . . . ?
Cl1B C25B C26B C27B 177.6(4) . . . . ?
C25B C26B C27B C22B 7.9(6) . . . . ?
C23B C22B C27B C26B -11.3(5) . . . . ?
C20 C22B C27B C26B -179.65(14) . . . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.313
_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_SPA208
_database_code_depnum_ccdc_archive 'CCDC 1945305'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H17 Br N2'
_chemical_formula_sum            'C27 H17 Br N2'
_chemical_formula_weight         449.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0018 0.0011 '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 0.0038 0.0023 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1086 1.8591 '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                   15.974(3)
_cell_length_b                   15.801(3)
_cell_length_c                   7.9960(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.10(3)
_cell_angle_gamma                90
_cell_volume                     1998.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    66411
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.334
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.890
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.600
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20887
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.538
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        21.100
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             5722
_reflns_number_gt                4808
_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-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.6'
_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)+(0.0608P)²+0.2784P] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0299(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5722
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0902
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.84233(2) 0.57237(2) -0.21825(2) 0.01664(7) Uani 1 1 d . . . . .
N1 N 0.24878(9) 0.62260(9) 0.34421(17) 0.0122(3) Uani 1 1 d . . . . .
N2 N 0.53758(10) 0.88208(10) 0.1127(2) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.24967(11) 0.59089(10) 0.5075(2) 0.0126(3) Uani 1 1 d . . . . .
C2 C 0.31870(11) 0.57038(10) 0.6280(2) 0.0149(3) Uani 1 1 d . . . . .
H2 H 0.375064 0.574019 0.603482 0.018 Uiso 1 1 calc R U . . .
C3 C 0.30126(12) 0.54445(11) 0.7854(2) 0.0179(3) Uani 1 1 d . . . . .
H3 H 0.346773 0.530040 0.870374 0.022 Uiso 1 1 calc R U . . .
C4 C 0.21844(13) 0.53902(12) 0.8220(2) 0.0203(4) Uani 1 1 d . . . . .
H4 H 0.208877 0.521161 0.931170 0.024 Uiso 1 1 calc R U . . .
C5 C 0.15011(12) 0.55913(13) 0.7024(2) 0.0196(4) Uani 1 1 d . . . . .
H5 H 0.093989 0.555128 0.728207 0.024 Uiso 1 1 calc R U . . .
C6 C 0.16552(11) 0.58552(11) 0.5425(2) 0.0144(3) Uani 1 1 d . . . . .
C7 C 0.11128(11) 0.61164(11) 0.3914(2) 0.0155(3) Uani 1 1 d . . . . .
C8 C 0.02341(11) 0.61147(13) 0.3445(2) 0.0218(4) Uani 1 1 d . . . . .
H8 H -0.013204 0.595281 0.422801 0.026 Uiso 1 1 calc R U . . .
C9 C -0.00892(12) 0.63542(14) 0.1815(3) 0.0258(4) Uani 1 1 d . . . . .
H9 H -0.068278 0.634027 0.146686 0.031 Uiso 1 1 calc R U . . .
C10 C 0.04475(12) 0.66166(13) 0.0674(2) 0.0238(4) Uani 1 1 d . . . . .
H10 H 0.020828 0.679221 -0.042677 0.029 Uiso 1 1 calc R U . . .
C11 C 0.13198(12) 0.66269(12) 0.1108(2) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.168086 0.680979 0.033140 0.022 Uiso 1 1 calc R U . . .
C12 C 0.16450(10) 0.63573(11) 0.2733(2) 0.0139(3) Uani 1 1 d . . . . .
C13 C 0.32056(10) 0.63227(11) 0.26057(19) 0.0111(3) Uani 1 1 d . . . . .
C14 C 0.38020(11) 0.56794(10) 0.2658(2) 0.0127(3) Uani 1 1 d . . . . .
H14 H 0.371656 0.516162 0.321355 0.015 Uiso 1 1 calc R U . . .
C15 C 0.45244(11) 0.57949(10) 0.1895(2) 0.0129(3) Uani 1 1 d . . . . .
H15 H 0.492866 0.535193 0.193066 0.015 Uiso 1 1 calc R U . . .
C16 C 0.46648(10) 0.65544(10) 0.10741(19) 0.0122(3) Uani 1 1 d . . . . .
C17 C 0.40373(10) 0.71808(11) 0.09739(19) 0.0134(3) Uani 1 1 d . . . . .
H17 H 0.410547 0.768800 0.036949 0.016 Uiso 1 1 calc R U . . .
C18 C 0.33190(10) 0.70715(10) 0.1743(2) 0.0136(3) Uani 1 1 d . . . . .
H18 H 0.290493 0.750616 0.168254 0.016 Uiso 1 1 calc R U . . .
C19 C 0.54586(11) 0.66503(11) 0.0381(2) 0.0139(3) Uani 1 1 d . . . . .
H19 H 0.570347 0.614096 0.004534 0.017 Uiso 1 1 calc R U . . .
C20 C 0.58916(10) 0.73680(10) 0.01541(19) 0.0118(3) Uani 1 1 d . . . . .
C21 C 0.55890(10) 0.81709(11) 0.0676(2) 0.0146(3) Uani 1 1 d . . . . .
C22 C 0.67120(10) 0.74008(10) -0.05238(19) 0.0119(3) Uani 1 1 d . . . . .
C23 C 0.71197(10) 0.66596(11) -0.09378(19) 0.0129(3) Uani 1 1 d . . . . .
H23 H 0.687335 0.612142 -0.079949 0.016 Uiso 1 1 calc R U . . .
C24 C 0.78869(10) 0.67223(11) -0.15515(19) 0.0125(3) Uani 1 1 d . . . . .
C25 C 0.82773(11) 0.74942(11) -0.1753(2) 0.0165(3) Uani 1 1 d . . . . .
H25 H 0.880901 0.752077 -0.215333 0.020 Uiso 1 1 calc R U . . .
C26 C 0.78674(12) 0.82250(12) -0.1351(2) 0.0179(3) Uani 1 1 d . . . . .
H26 H 0.811890 0.876066 -0.148959 0.022 Uiso 1 1 calc R U . . .
C27 C 0.70931(11) 0.81838(11) -0.0748(2) 0.0150(3) Uani 1 1 d . . . . .
H27 H 0.682004 0.869110 -0.048568 0.018 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
Br1 C24 1.8974(17) . ?
N1 C1 1.396(2) . ?
N1 C12 1.401(2) . ?
N1 C13 1.415(2) . ?
N2 C21 1.156(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.414(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(2) . ?
C7 C8 1.401(2) . ?
C7 C12 1.409(2) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.390(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.401(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(2) . ?
C16 C19 1.461(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.354(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.440(2) . ?
C20 C22 1.488(2) . ?
C22 C27 1.401(2) . ?
C22 C23 1.402(2) . ?
C23 C24 1.386(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(2) . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 108.32(14) . . ?
C1 N1 C13 125.34(14) . . ?
C12 N1 C13 126.11(14) . . ?
N1 C1 C2 129.17(16) . . ?
N1 C1 C6 108.78(14) . . ?
C2 C1 C6 121.98(15) . . ?
C3 C2 C1 117.03(16) . . ?
C3 C2 H2 121.5 . . ?
C1 C2 H2 121.5 . . ?
C2 C3 C4 121.64(17) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.30(16) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.49(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.57(16) . . ?
C5 C6 C7 133.43(17) . . ?
C1 C6 C7 107.00(15) . . ?
C8 C7 C12 119.84(16) . . ?
C8 C7 C6 133.13(17) . . ?
C12 C7 C6 106.88(15) . . ?
C9 C8 C7 118.54(18) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C8 C9 C10 120.85(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.73(17) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.26(18) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 N1 129.22(16) . . ?
C11 C12 C7 121.71(16) . . ?
N1 C12 C7 108.95(15) . . ?
C14 C13 C18 119.96(15) . . ?
C14 C13 N1 120.31(15) . . ?
C18 C13 N1 119.73(15) . . ?
C13 C14 C15 119.89(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 121.01(15) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 118.09(15) . . ?
C15 C16 C19 118.10(15) . . ?
C17 C16 C19 123.80(15) . . ?
C18 C17 C16 121.06(15) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 119.89(15) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 C16 128.66(16) . . ?
C20 C19 H19 115.7 . . ?
C16 C19 H19 115.7 . . ?
C19 C20 C21 120.01(15) . . ?
C19 C20 C22 124.82(15) . . ?
C21 C20 C22 115.07(14) . . ?
N2 C21 C20 177.46(17) . . ?
C27 C22 C23 118.86(15) . . ?
C27 C22 C20 119.87(15) . . ?
C23 C22 C20 121.27(14) . . ?
C24 C23 C22 119.14(15) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 122.49(16) . . ?
C23 C24 Br1 119.31(12) . . ?
C25 C24 Br1 118.19(13) . . ?
C26 C25 C24 118.02(16) . . ?
C26 C25 H25 121.0 . . ?
C24 C25 H25 121.0 . . ?
C25 C26 C27 120.87(16) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 120.61(16) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?

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
C12 N1 C1 C2 -178.13(17) . . . . ?
C13 N1 C1 C2 7.1(3) . . . . ?
C12 N1 C1 C6 -1.31(18) . . . . ?
C13 N1 C1 C6 -176.09(15) . . . . ?
N1 C1 C2 C3 176.29(16) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -179.29(18) . . . . ?
N1 C1 C6 C5 -176.95(16) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C7 2.52(18) . . . . ?
C2 C1 C6 C7 179.61(15) . . . . ?
C5 C6 C7 C8 -8.0(3) . . . . ?
C1 C6 C7 C8 172.62(19) . . . . ?
C5 C6 C7 C12 176.61(19) . . . . ?
C1 C6 C7 C12 -2.76(19) . . . . ?
C12 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 -175.01(19) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C8 C9 C10 C11 1.7(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 N1 173.18(17) . . . . ?
C10 C11 C12 C7 -2.5(3) . . . . ?
C1 N1 C12 C11 -176.59(17) . . . . ?
C13 N1 C12 C11 -1.9(3) . . . . ?
C1 N1 C12 C7 -0.46(19) . . . . ?
C13 N1 C12 C7 174.27(15) . . . . ?
C8 C7 C12 C11 2.4(3) . . . . ?
C6 C7 C12 C11 178.48(16) . . . . ?
C8 C7 C12 N1 -174.11(16) . . . . ?
C6 C7 C12 N1 2.00(19) . . . . ?
C1 N1 C13 C14 44.9(2) . . . . ?
C12 N1 C13 C14 -128.98(17) . . . . ?
C1 N1 C13 C18 -134.35(17) . . . . ?
C12 N1 C13 C18 51.8(2) . . . . ?
C18 C13 C14 C15 2.1(2) . . . . ?
N1 C13 C14 C15 -177.17(14) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C17 -3.0(2) . . . . ?
C14 C15 C16 C19 176.68(15) . . . . ?
C15 C16 C17 C18 3.4(2) . . . . ?
C19 C16 C17 C18 -176.17(15) . . . . ?
C16 C17 C18 C13 -1.2(2) . . . . ?
C14 C13 C18 C17 -1.6(2) . . . . ?
N1 C13 C18 C17 177.65(14) . . . . ?
C15 C16 C19 C20 -151.39(17) . . . . ?
C17 C16 C19 C20 28.2(3) . . . . ?
C16 C19 C20 C21 2.1(3) . . . . ?
C16 C19 C20 C22 178.29(15) . . . . ?
C19 C20 C22 C27 178.28(15) . . . . ?
C21 C20 C22 C27 -5.4(2) . . . . ?
C19 C20 C22 C23 -2.1(2) . . . . ?
C21 C20 C22 C23 174.20(14) . . . . ?
C27 C22 C23 C24 0.2(2) . . . . ?
C20 C22 C23 C24 -179.44(14) . . . . ?
C22 C23 C24 C25 0.9(2) . . . . ?
C22 C23 C24 Br1 -177.97(11) . . . . ?
C23 C24 C25 C26 -1.3(2) . . . . ?
Br1 C24 C25 C26 177.58(13) . . . . ?
C24 C25 C26 C27 0.7(3) . . . . ?
C25 C26 C27 C22 0.4(3) . . . . ?
C23 C22 C27 C26 -0.8(2) . . . . ?
C20 C22 C27 C26 178.82(15) . . . . ?

_refine_diff_density_max         0.595
_refine_diff_density_min         -1.168
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_SPA297
_database_code_depnum_ccdc_archive 'CCDC 1945300'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 F N2'
_chemical_formula_sum            'C27 H17 F N2'
_chemical_formula_weight         388.42

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'
F F 0.0134 0.0079 '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                   9.4070(19)
_cell_length_b                   13.348(3)
_cell_length_c                   15.571(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.33(3)
_cell_angle_gamma                90
_cell_volume                     1939.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    58682
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.963
_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            18843
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5029
_reflns_number_gt                4209
_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, 2015a)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4(Putz&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)+(0.0898P)²+0.1466P] 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         5029
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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 0.19077(11) 0.72497(7) 0.86581(6) 0.0438(2) Uani 1 1 d . . . . .
N2 N 0.15346(15) 0.23731(9) 0.71233(9) 0.0672(3) Uani 1 1 d . . . . .
C1 C 0.13906(12) 0.70836(8) 0.94446(7) 0.0432(2) Uani 1 1 d . . . . .
C2 C 0.11725(14) 0.61853(9) 0.98633(8) 0.0508(3) Uani 1 1 d . . . . .
H2 H 0.133121 0.556527 0.960558 0.061 Uiso 1 1 calc R U . . .
C3 C 0.07153(16) 0.62371(10) 1.06698(9) 0.0582(3) Uani 1 1 d . . . . .
H3 H 0.056861 0.563953 1.096564 0.070 Uiso 1 1 calc R U . . .
C4 C 0.04639(16) 0.71536(11) 1.10598(9) 0.0588(3) Uani 1 1 d . . . . .
H4 H 0.012763 0.716415 1.160286 0.071 Uiso 1 1 calc R U . . .
C5 C 0.07078(14) 0.80411(10) 1.06500(8) 0.0511(3) Uani 1 1 d . . . . .
H5 H 0.055830 0.865752 1.091633 0.061 Uiso 1 1 calc R U . . .
C6 C 0.11772(12) 0.80157(8) 0.98382(7) 0.0435(2) Uani 1 1 d . . . . .
C7 C 0.15957(11) 0.87790(8) 0.92652(7) 0.0430(2) Uani 1 1 d . . . . .
C8 C 0.16475(12) 0.98241(8) 0.93072(8) 0.0479(3) Uani 1 1 d . . . . .
H8 H 0.138612 1.016178 0.979311 0.057 Uiso 1 1 calc R U . . .
C9 C 0.20870(13) 1.03560(9) 0.86269(9) 0.0521(3) Uani 1 1 d . . . . .
H9 H 0.212508 1.105933 0.864973 0.063 Uiso 1 1 calc R U . . .
C10 C 0.24748(13) 0.98532(9) 0.79058(9) 0.0513(3) Uani 1 1 d . . . . .
H10 H 0.274675 1.022849 0.744262 0.062 Uiso 1 1 calc R U . . .
C11 C 0.24705(12) 0.88142(8) 0.78530(8) 0.0466(3) Uani 1 1 d . . . . .
H11 H 0.275143 0.848231 0.736954 0.056 Uiso 1 1 calc R U . . .
C12 C 0.20347(11) 0.82837(8) 0.85427(7) 0.0418(2) Uani 1 1 d . . . . .
C13 C 0.22884(11) 0.64977(8) 0.80857(7) 0.0409(2) Uani 1 1 d . . . . .
C14 C 0.13518(11) 0.57118(8) 0.78383(7) 0.0409(2) Uani 1 1 d . . . . .
H14 H 0.045792 0.568431 0.804685 0.049 Uiso 1 1 calc R U . . .
C15 C 0.17273(11) 0.49702(7) 0.72872(7) 0.0401(2) Uani 1 1 d . . . . .
H15 H 0.109826 0.443278 0.713804 0.048 Uiso 1 1 calc R U . . .
C16 C 0.30416(12) 0.50152(7) 0.69493(7) 0.0401(2) Uani 1 1 d . . . . .
C17 C 0.39452(12) 0.58277(8) 0.71848(8) 0.0459(3) Uani 1 1 d . . . . .
H17 H 0.481092 0.588413 0.694660 0.055 Uiso 1 1 calc R U . . .
C18 C 0.35986(12) 0.65495(8) 0.77584(8) 0.0464(3) Uani 1 1 d . . . . .
H18 H 0.424249 0.707295 0.792723 0.056 Uiso 1 1 calc R U . . .
C19 C 0.35021(11) 0.43005(8) 0.63274(7) 0.0418(2) Uani 1 1 d . . . . .
H19 H 0.415592 0.455888 0.597537 0.050 Uiso 1 1 calc R U . . .
C20 C 0.31435(11) 0.33332(8) 0.61761(7) 0.0388(2) Uani 1 1 d . . . . .
C21 C 0.22245(13) 0.28209(8) 0.67067(8) 0.0463(3) Uani 1 1 d . . . . .
F1A F 0.5395(6) 0.0771(4) 0.3801(5) 0.0965(16) Uani 0.486(10) 1 d . . P A 1
C22A C 0.3652(9) 0.2637(11) 0.5492(6) 0.046(2) Uani 0.486(10) 1 d . . P A 1
C23A C 0.3296(7) 0.1639(4) 0.5447(6) 0.0710(17) Uani 0.486(10) 1 d . . P A 1
H23A H 0.265999 0.138158 0.581103 0.085 Uiso 0.486(10) 1 calc R U P A 1
C24A C 0.3869(8) 0.0999(5) 0.4865(6) 0.091(2) Uani 0.486(10) 1 d . . P A 1
H24A H 0.359366 0.032241 0.481934 0.109 Uiso 0.486(10) 1 calc R U P A 1
C25A C 0.4827(7) 0.1375(5) 0.4368(5) 0.0649(14) Uani 0.486(10) 1 d . . P A 1
C26A C 0.5336(7) 0.2470(7) 0.4451(5) 0.0478(19) Uani 0.486(10) 1 d . . P A 1
H26A H 0.596904 0.274297 0.409246 0.057 Uiso 0.486(10) 1 calc R U P A 1
C27A C 0.48187(13) 0.30134(9) 0.50702(8) 0.0479(3) Uani 0.486(10) 1 d . . P A 1
H27A H 0.522126 0.364189 0.522788 0.057 Uiso 0.486(10) 1 calc R U P A 1
F2B F 0.4954(6) 0.1172(5) 0.3457(3) 0.0911(15) Uani 0.514(10) 1 d . . P A 2
C22B C 0.3692(9) 0.2767(10) 0.5498(6) 0.0396(14) Uani 0.514(10) 1 d . . P A 2
C23B C 0.2865(5) 0.1959(4) 0.5114(3) 0.0560(11) Uani 0.514(10) 1 d . . P A 2
H23B H 0.200060 0.179008 0.532178 0.067 Uiso 0.514(10) 1 calc R U P A 2
C24B C 0.3299(6) 0.1416(5) 0.4443(4) 0.0743(16) Uani 0.514(10) 1 d . . P A 2
H24B H 0.276651 0.086092 0.421193 0.089 Uiso 0.514(10) 1 calc R U P A 2
C25B C 0.4528(6) 0.1702(5) 0.4116(3) 0.0566(11) Uani 0.514(10) 1 d . . P A 2
C26B C 0.5273(8) 0.2386(7) 0.4422(5) 0.063(3) Uani 0.514(10) 1 d . . P A 2
H26B H 0.616428 0.250253 0.422675 0.076 Uiso 0.514(10) 1 calc R U P A 2
C27B C 0.48187(13) 0.30134(9) 0.50702(8) 0.0479(3) Uani 0.514(10) 1 d . . P A 2
H27B H 0.530976 0.361705 0.520874 0.057 Uiso 0.514(10) 1 calc R U P A 2


_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 C1 1.3920(15) . ?
N1 C12 1.3988(14) . ?
N1 C13 1.4183(13) . ?
N2 C21 1.1432(16) . ?
C1 C2 1.3925(16) . ?
C1 C6 1.4126(15) . ?
C2 C3 1.3802(19) . ?
C2 H2 0.9400 . ?
C3 C4 1.3992(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.3915(17) . ?
C5 H5 0.9400 . ?
C6 C7 1.4418(16) . ?
C7 C8 1.3971(16) . ?
C7 C12 1.4113(15) . ?
C8 C9 1.3816(19) . ?
C8 H8 0.9400 . ?
C9 C10 1.3960(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.3892(16) . ?
C10 H10 0.9400 . ?
C11 C12 1.3911(16) . ?
C11 H11 0.9400 . ?
C13 C14 1.3923(15) . ?
C13 C18 1.3943(16) . ?
C14 C15 1.3850(14) . ?
C14 H14 0.9400 . ?
C15 C16 1.4053(15) . ?
C15 H15 0.9400 . ?
C16 C17 1.3977(15) . ?
C16 C19 1.4639(14) . ?
C17 C18 1.3807(15) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3475(15) . ?
C19 H19 0.9400 . ?
C20 C21 1.4422(15) . ?
C20 C22B 1.447(10) . ?
C20 C22A 1.535(10) . ?
F1A C25A 1.355(6) . ?
C22A C23A 1.374(15) . ?
C22A C27A 1.439(10) . ?
C23A C24A 1.402(6) . ?
C23A H23A 0.9400 . ?
C24A C25A 1.356(7) . ?
C24A H24A 0.9400 . ?
C25A C26A 1.539(11) . ?
C26A C27A 1.346(8) . ?
C26A H26A 0.9400 . ?
C27A H27A 0.9400 . ?
F2B C25B 1.349(5) . ?
C22B C27B 1.361(10) . ?
C22B C23B 1.417(12) . ?
C23B C24B 1.376(5) . ?
C23B H23B 0.9400 . ?
C24B C25B 1.375(6) . ?
C24B H24B 0.9400 . ?
C25B C26B 1.211(10) . ?
C26B C27B 1.420(7) . ?
C26B H26B 0.9400 . ?
C27B H27B 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
C1 N1 C12 108.38(9) . . ?
C1 N1 C13 125.78(9) . . ?
C12 N1 C13 125.81(9) . . ?
N1 C1 C2 129.64(10) . . ?
N1 C1 C6 109.05(10) . . ?
C2 C1 C6 121.18(11) . . ?
C3 C2 C1 117.68(11) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.88(12) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.21(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.36(11) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 119.65(11) . . ?
C5 C6 C7 133.50(10) . . ?
C1 C6 C7 106.78(10) . . ?
C8 C7 C12 119.54(11) . . ?
C8 C7 C6 133.41(11) . . ?
C12 C7 C6 107.04(9) . . ?
C9 C8 C7 119.29(11) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.27(11) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 121.90(12) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 117.48(11) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 N1 129.78(10) . . ?
C11 C12 C7 121.46(10) . . ?
N1 C12 C7 108.74(10) . . ?
C14 C13 C18 119.60(10) . . ?
C14 C13 N1 120.37(10) . . ?
C18 C13 N1 120.03(10) . . ?
C15 C14 C13 120.50(10) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.49(10) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 118.01(9) . . ?
C17 C16 C19 117.24(10) . . ?
C15 C16 C19 124.65(10) . . ?
C18 C17 C16 121.68(10) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.64(10) . . ?
C17 C18 H18 120.2 . . ?
C13 C18 H18 120.2 . . ?
C20 C19 C16 130.65(10) . . ?
C20 C19 H19 114.7 . . ?
C16 C19 H19 114.7 . . ?
C19 C20 C21 120.61(9) . . ?
C19 C20 C22B 121.6(5) . . ?
C21 C20 C22B 117.8(5) . . ?
C19 C20 C22A 127.4(5) . . ?
C21 C20 C22A 111.9(5) . . ?
N2 C21 C20 176.63(13) . . ?
C23A C22A C27A 120.7(7) . . ?
C23A C22A C20 121.8(7) . . ?
C27A C22A C20 115.4(9) . . ?
C22A C23A C24A 120.8(5) . . ?
C22A C23A H23A 119.6 . . ?
C24A C23A H23A 119.6 . . ?
C25A C24A C23A 118.8(4) . . ?
C25A C24A H24A 120.6 . . ?
C23A C24A H24A 120.6 . . ?
F1A C25A C24A 119.8(5) . . ?
F1A C25A C26A 118.4(5) . . ?
C24A C25A C26A 121.7(5) . . ?
C27A C26A C25A 115.8(6) . . ?
C27A C26A H26A 122.1 . . ?
C25A C26A H26A 122.1 . . ?
C26A C27A C22A 120.4(6) . . ?
C26A C27A H27A 119.8 . . ?
C22A C27A H27A 119.8 . . ?
C27B C22B C23B 113.4(7) . . ?
C27B C22B C20 127.1(9) . . ?
C23B C22B C20 118.5(7) . . ?
C24B C23B C22B 121.4(5) . . ?
C24B C23B H23B 119.3 . . ?
C22B C23B H23B 119.3 . . ?
C25B C24B C23B 118.7(3) . . ?
C25B C24B H24B 120.7 . . ?
C23B C24B H24B 120.7 . . ?
C26B C25B F2B 118.8(5) . . ?
C26B C25B C24B 122.4(5) . . ?
F2B C25B C24B 118.7(4) . . ?
C25B C26B C27B 120.8(6) . . ?
C25B C26B H26B 119.6 . . ?
C27B C26B H26B 119.6 . . ?
C22B C27B C26B 121.9(6) . . ?
C22B C27B H27B 119.0 . . ?
C26B C27B H27B 119.0 . . ?

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
C12 N1 C1 C2 -175.63(12) . . . . ?
C13 N1 C1 C2 2.4(2) . . . . ?
C12 N1 C1 C6 0.21(13) . . . . ?
C13 N1 C1 C6 178.20(10) . . . . ?
N1 C1 C2 C3 176.56(12) . . . . ?
C6 C1 C2 C3 1.15(19) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C4 C5 C6 C1 0.29(18) . . . . ?
C4 C5 C6 C7 -176.23(12) . . . . ?
N1 C1 C6 C5 -177.81(10) . . . . ?
C2 C1 C6 C5 -1.56(18) . . . . ?
N1 C1 C6 C7 -0.45(13) . . . . ?
C2 C1 C6 C7 175.81(11) . . . . ?
C5 C6 C7 C8 -1.9(2) . . . . ?
C1 C6 C7 C8 -178.76(12) . . . . ?
C5 C6 C7 C12 177.35(12) . . . . ?
C1 C6 C7 C12 0.51(12) . . . . ?
C12 C7 C8 C9 1.97(17) . . . . ?
C6 C7 C8 C9 -178.84(12) . . . . ?
C7 C8 C9 C10 0.00(17) . . . . ?
C8 C9 C10 C11 -1.67(19) . . . . ?
C9 C10 C11 C12 1.26(18) . . . . ?
C10 C11 C12 N1 179.06(12) . . . . ?
C10 C11 C12 C7 0.77(16) . . . . ?
C1 N1 C12 C11 -178.34(11) . . . . ?
C13 N1 C12 C11 3.67(18) . . . . ?
C1 N1 C12 C7 0.12(12) . . . . ?
C13 N1 C12 C7 -177.87(10) . . . . ?
C8 C7 C12 C11 -2.39(16) . . . . ?
C6 C7 C12 C11 178.22(10) . . . . ?
C8 C7 C12 N1 179.00(10) . . . . ?
C6 C7 C12 N1 -0.39(12) . . . . ?
C1 N1 C13 C14 49.78(16) . . . . ?
C12 N1 C13 C14 -132.58(12) . . . . ?
C1 N1 C13 C18 -131.06(12) . . . . ?
C12 N1 C13 C18 46.58(16) . . . . ?
C18 C13 C14 C15 1.57(16) . . . . ?
N1 C13 C14 C15 -179.27(10) . . . . ?
C13 C14 C15 C16 -1.86(16) . . . . ?
C14 C15 C16 C17 -0.17(16) . . . . ?
C14 C15 C16 C19 -176.54(10) . . . . ?
C15 C16 C17 C18 2.54(17) . . . . ?
C19 C16 C17 C18 179.18(11) . . . . ?
C16 C17 C18 C13 -2.86(18) . . . . ?
C14 C13 C18 C17 0.76(17) . . . . ?
N1 C13 C18 C17 -178.40(10) . . . . ?
C17 C16 C19 C20 157.09(12) . . . . ?
C15 C16 C19 C20 -26.51(19) . . . . ?
C16 C19 C20 C21 -4.12(19) . . . . ?
C16 C19 C20 C22B 177.6(4) . . . . ?
C16 C19 C20 C22A 178.5(5) . . . . ?
C19 C20 C22A C23A 174.8(7) . . . . ?
C21 C20 C22A C23A -2.8(10) . . . . ?
C19 C20 C22A C27A 11.2(10) . . . . ?
C21 C20 C22A C27A -166.4(5) . . . . ?
C27A C22A C23A C24A -12.0(12) . . . . ?
C20 C22A C23A C24A -174.7(6) . . . . ?
C22A C23A C24A C25A 2.5(10) . . . . ?
C23A C24A C25A F1A 180.0(5) . . . . ?
C23A C24A C25A C26A 2.2(9) . . . . ?
F1A C25A C26A C27A -175.1(5) . . . . ?
C24A C25A C26A C27A 2.7(9) . . . . ?
C25A C26A C27A C22A -12.0(9) . . . . ?
C23A C22A C27A C26A 17.2(12) . . . . ?
C20 C22A C27A C26A -179.1(6) . . . . ?
C19 C20 C22B C27B 15.5(10) . . . . ?
C21 C20 C22B C27B -162.8(6) . . . . ?
C19 C20 C22B C23B -152.6(6) . . . . ?
C21 C20 C22B C23B 29.1(9) . . . . ?
C27B C22B C23B C24B 7.7(10) . . . . ?
C20 C22B C23B C24B 177.4(5) . . . . ?
C22B C23B C24B C25B -3.2(8) . . . . ?
C23B C24B C25B C26B 3.3(9) . . . . ?
C23B C24B C25B F2B -179.9(4) . . . . ?
F2B C25B C26B C27B 175.1(6) . . . . ?
C24B C25B C26B C27B -8.0(12) . . . . ?
C23B C22B C27B C26B -12.4(10) . . . . ?
C20 C22B C27B C26B 179.0(7) . . . . ?
C25B C26B C27B C22B 13.3(12) . . . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_SPA432
_database_code_depnum_ccdc_archive 'CCDC 1945302'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2019-09-26 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         'C27 H17 Cl N2'
_chemical_formula_sum            'C27 H17 Cl N2'
_chemical_formula_weight         404.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0019 0.0011 '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 0.0040 0.0024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1166 0.1176 '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                   14.470(3)
_cell_length_b                   8.4370(17)
_cell_length_c                   17.241(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.23(3)
_cell_angle_gamma                90
_cell_volume                     1975.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    64029
_cell_measurement_theta_min      0.350
_cell_measurement_theta_max      33.679

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.925
_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     0.610
_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            19626
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        21.469
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             5321
_reflns_number_gt                4594
_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)+(0.0941P)²+0.2522P] 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         5321
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.39051(3) 0.39596(5) 0.94037(2) 0.04634(14) Uani 1 1 d . . . . .
N1 N 0.29368(7) 0.61800(13) 0.29950(6) 0.0252(2) Uani 1 1 d . . . . .
N2 N 0.00595(9) 0.66826(18) 0.56129(8) 0.0437(3) Uani 1 1 d . . . . .
C1 C 0.23110(8) 0.55938(15) 0.22358(6) 0.0240(2) Uani 1 1 d . . . . .
C2 C 0.14322(9) 0.47586(17) 0.20596(7) 0.0311(3) Uani 1 1 d . . . . .
H2 H 0.116216 0.454024 0.247177 0.037 Uiso 1 1 calc R U . . .
C3 C 0.09721(10) 0.42626(18) 0.12501(8) 0.0361(3) Uani 1 1 d . . . . .
H3 H 0.037682 0.369795 0.111134 0.043 Uiso 1 1 calc R U . . .
C4 C 0.13726(10) 0.45825(19) 0.06348(8) 0.0364(3) Uani 1 1 d . . . . .
H4 H 0.103873 0.424167 0.009030 0.044 Uiso 1 1 calc R U . . .
C5 C 0.22511(9) 0.53916(17) 0.08169(7) 0.0308(3) Uani 1 1 d . . . . .
H5 H 0.251944 0.559760 0.040235 0.037 Uiso 1 1 calc R U . . .
C6 C 0.27360(8) 0.59006(14) 0.16299(7) 0.0240(2) Uani 1 1 d . . . . .
C7 C 0.36632(8) 0.66832(14) 0.20382(7) 0.0242(2) Uani 1 1 d . . . . .
C8 C 0.44137(9) 0.72453(17) 0.17733(8) 0.0319(3) Uani 1 1 d . . . . .
H8 H 0.435795 0.716274 0.121520 0.038 Uiso 1 1 calc R U . . .
C9 C 0.52402(10) 0.79255(18) 0.23459(9) 0.0373(3) Uani 1 1 d . . . . .
H9 H 0.575122 0.829732 0.217458 0.045 Uiso 1 1 calc R U . . .
C10 C 0.53242(9) 0.80661(17) 0.31747(9) 0.0355(3) Uani 1 1 d . . . . .
H10 H 0.588933 0.854395 0.354968 0.043 Uiso 1 1 calc R U . . .
C11 C 0.45944(9) 0.75181(15) 0.34585(7) 0.0291(2) Uani 1 1 d . . . . .
H11 H 0.465295 0.761662 0.401656 0.035 Uiso 1 1 calc R U . . .
C12 C 0.37711(8) 0.68156(14) 0.28808(7) 0.0235(2) Uani 1 1 d . . . . .
C13 C 0.28035(8) 0.59591(15) 0.37636(6) 0.0250(2) Uani 1 1 d . . . . .
C14 C 0.19404(8) 0.64774(17) 0.38744(7) 0.0304(3) Uani 1 1 d . . . . .
H14 H 0.146307 0.702923 0.344777 0.036 Uiso 1 1 calc R U . . .
C15 C 0.17847(9) 0.61814(17) 0.46109(7) 0.0307(3) Uani 1 1 d . . . . .
H15 H 0.119469 0.651387 0.467405 0.037 Uiso 1 1 calc R U . . .
C16 C 0.24961(8) 0.53927(15) 0.52621(7) 0.0260(2) Uani 1 1 d . . . . .
C17 C 0.33692(9) 0.49276(17) 0.51447(7) 0.0304(3) Uani 1 1 d . . . . .
H17 H 0.386252 0.441823 0.557800 0.037 Uiso 1 1 calc R U . . .
C18 C 0.35223(9) 0.52002(17) 0.44069(7) 0.0302(3) Uani 1 1 d . . . . .
H18 H 0.411201 0.487181 0.434183 0.036 Uiso 1 1 calc R U . . .
C19 C 0.24168(9) 0.49820(16) 0.60606(7) 0.0275(2) Uani 1 1 d . . . . .
H19 H 0.296087 0.442125 0.641441 0.033 Uiso 1 1 calc R U . . .
C20 C 0.17025(8) 0.52629(15) 0.63823(7) 0.0249(2) Uani 1 1 d . . . . .
C21 C 0.07991(9) 0.60684(16) 0.59334(7) 0.0298(3) Uani 1 1 d . . . . .
C22 C 0.17832(9) 0.47251(14) 0.72248(7) 0.0254(2) Uani 1 1 d . . . . .
C23 C 0.27059(9) 0.45803(15) 0.78468(7) 0.0279(2) Uani 1 1 d . . . . .
H23 H 0.328174 0.485799 0.774350 0.033 Uiso 1 1 calc R U . . .
C24 C 0.27598(10) 0.40217(16) 0.86177(7) 0.0306(3) Uani 1 1 d . . . . .
C25 C 0.19311(10) 0.35629(18) 0.87888(8) 0.0357(3) Uani 1 1 d . . . . .
H25 H 0.198688 0.313907 0.930733 0.043 Uiso 1 1 calc R U . . .
C26 C 0.10178(10) 0.3745(2) 0.81759(9) 0.0387(3) Uani 1 1 d . . . . .
H26 H 0.044502 0.346187 0.828294 0.046 Uiso 1 1 calc R U . . .
C27 C 0.09405(9) 0.43427(18) 0.74037(8) 0.0332(3) Uani 1 1 d . . . . .
H27 H 0.031538 0.449007 0.699933 0.040 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
Cl1 C24 1.7415(15) . ?
N1 C12 1.3957(14) . ?
N1 C1 1.3993(14) . ?
N1 C13 1.4159(14) . ?
N2 C21 1.1447(18) . ?
C1 C2 1.3924(16) . ?
C1 C6 1.4074(15) . ?
C2 C3 1.3869(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.3998(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.3801(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.4005(16) . ?
C5 H5 0.9400 . ?
C6 C7 1.4416(16) . ?
C7 C8 1.3985(16) . ?
C7 C12 1.4107(15) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9400 . ?
C9 C10 1.397(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.3876(17) . ?
C10 H10 0.9400 . ?
C11 C12 1.3936(16) . ?
C11 H11 0.9400 . ?
C13 C18 1.3872(17) . ?
C13 C14 1.3973(16) . ?
C14 C15 1.3868(16) . ?
C14 H14 0.9400 . ?
C15 C16 1.4013(16) . ?
C15 H15 0.9400 . ?
C16 C17 1.4028(16) . ?
C16 C19 1.4621(15) . ?
C17 C18 1.3838(15) . ?
C17 H17 0.9400 . ?
C18 H18 0.9400 . ?
C19 C20 1.3523(15) . ?
C19 H19 0.9400 . ?
C20 C21 1.4387(17) . ?
C20 C22 1.4874(15) . ?
C22 C27 1.3951(16) . ?
C22 C23 1.3991(17) . ?
C23 C24 1.3867(16) . ?
C23 H23 0.9400 . ?
C24 C25 1.3855(18) . ?
C25 C26 1.386(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.3916(18) . ?
C26 H26 0.9400 . ?
C27 H27 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
C12 N1 C1 108.38(9) . . ?
C12 N1 C13 125.94(10) . . ?
C1 N1 C13 125.13(10) . . ?
C2 C1 N1 129.03(10) . . ?
C2 C1 C6 122.11(10) . . ?
N1 C1 C6 108.77(10) . . ?
C3 C2 C1 117.17(11) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.60(12) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.87(11) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.86(11) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.36(11) . . ?
C5 C6 C7 133.53(11) . . ?
C1 C6 C7 107.06(9) . . ?
C8 C7 C12 119.17(11) . . ?
C8 C7 C6 133.82(11) . . ?
C12 C7 C6 106.98(9) . . ?
C9 C8 C7 118.97(11) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 120.85(12) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 121.65(12) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 117.16(11) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 121.4 . . ?
C11 C12 N1 129.05(10) . . ?
C11 C12 C7 122.17(10) . . ?
N1 C12 C7 108.76(10) . . ?
C18 C13 C14 119.58(10) . . ?
C18 C13 N1 120.12(10) . . ?
C14 C13 N1 120.28(11) . . ?
C15 C14 C13 120.31(11) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.81(11) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 117.77(10) . . ?
C15 C16 C19 126.29(10) . . ?
C17 C16 C19 115.93(11) . . ?
C18 C17 C16 121.64(11) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 119.84(11) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 C16 131.65(11) . . ?
C20 C19 H19 114.2 . . ?
C16 C19 H19 114.2 . . ?
C19 C20 C21 122.91(10) . . ?
C19 C20 C22 122.28(11) . . ?
C21 C20 C22 114.80(10) . . ?
N2 C21 C20 175.90(13) . . ?
C27 C22 C23 119.07(11) . . ?
C27 C22 C20 120.46(11) . . ?
C23 C22 C20 120.47(10) . . ?
C24 C23 C22 119.13(11) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 122.21(12) . . ?
C25 C24 Cl1 119.12(10) . . ?
C23 C24 Cl1 118.63(10) . . ?
C24 C25 C26 118.29(11) . . ?
C24 C25 H25 120.9 . . ?
C26 C25 H25 120.9 . . ?
C25 C26 C27 120.64(12) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 120.54(12) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?

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
C12 N1 C1 C2 174.93(13) . . . . ?
C13 N1 C1 C2 3.0(2) . . . . ?
C12 N1 C1 C6 -1.74(13) . . . . ?
C13 N1 C1 C6 -173.67(11) . . . . ?
N1 C1 C2 C3 -177.69(13) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C1 -0.82(19) . . . . ?
C4 C5 C6 C7 176.39(13) . . . . ?
C2 C1 C6 C5 1.78(19) . . . . ?
N1 C1 C6 C5 178.73(11) . . . . ?
C2 C1 C6 C7 -176.10(12) . . . . ?
N1 C1 C6 C7 0.85(13) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C1 C6 C7 C8 178.62(14) . . . . ?
C5 C6 C7 C12 -177.11(13) . . . . ?
C1 C6 C7 C12 0.35(13) . . . . ?
C12 C7 C8 C9 -0.38(19) . . . . ?
C6 C7 C8 C9 -178.49(13) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 N1 -179.58(12) . . . . ?
C10 C11 C12 C7 -1.14(19) . . . . ?
C1 N1 C12 C11 -179.44(12) . . . . ?
C13 N1 C12 C11 -7.6(2) . . . . ?
C1 N1 C12 C7 1.96(13) . . . . ?
C13 N1 C12 C7 173.81(11) . . . . ?
C8 C7 C12 C11 1.29(18) . . . . ?
C6 C7 C12 C11 179.87(11) . . . . ?
C8 C7 C12 N1 -179.99(11) . . . . ?
C6 C7 C12 N1 -1.42(13) . . . . ?
C12 N1 C13 C18 -49.96(18) . . . . ?
C1 N1 C13 C18 120.57(14) . . . . ?
C12 N1 C13 C14 131.21(14) . . . . ?
C1 N1 C13 C14 -58.25(17) . . . . ?
C18 C13 C14 C15 -2.5(2) . . . . ?
N1 C13 C14 C15 176.31(12) . . . . ?
C13 C14 C15 C16 1.5(2) . . . . ?
C14 C15 C16 C17 0.5(2) . . . . ?
C14 C15 C16 C19 -178.77(13) . . . . ?
C15 C16 C17 C18 -1.4(2) . . . . ?
C19 C16 C17 C18 177.92(13) . . . . ?
C16 C17 C18 C13 0.4(2) . . . . ?
C14 C13 C18 C17 1.6(2) . . . . ?
N1 C13 C18 C17 -177.24(12) . . . . ?
C15 C16 C19 C20 -2.0(2) . . . . ?
C17 C16 C19 C20 178.74(14) . . . . ?
C16 C19 C20 C21 1.6(2) . . . . ?
C16 C19 C20 C22 -179.90(13) . . . . ?
C19 C20 C22 C27 -149.81(13) . . . . ?
C21 C20 C22 C27 28.83(17) . . . . ?
C19 C20 C22 C23 29.54(19) . . . . ?
C21 C20 C22 C23 -151.81(12) . . . . ?
C27 C22 C23 C24 1.66(19) . . . . ?
C20 C22 C23 C24 -177.70(12) . . . . ?
C22 C23 C24 C25 1.6(2) . . . . ?
C22 C23 C24 Cl1 -176.20(10) . . . . ?
C23 C24 C25 C26 -3.1(2) . . . . ?
Cl1 C24 C25 C26 174.70(11) . . . . ?
C24 C25 C26 C27 1.3(2) . . . . ?
C25 C26 C27 C22 1.9(2) . . . . ?
C23 C22 C27 C26 -3.4(2) . . . . ?
C20 C22 C27 C26 175.95(13) . . . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058

