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

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

data_6
_audit_block_doi                 10.5517/ccdc.csd.cc27tpvm
_database_code_depnum_ccdc_archive 'CCDC 2080281'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202103152 2021
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H12 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5514(2)
_cell_length_b                   12.5565(2)
_cell_length_c                   23.3730(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2509.69(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6369
_cell_measurement_temperature    120
_cell_measurement_theta_max      75.8890
_cell_measurement_theta_min      3.7590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 15 0.0220
0 1 -15 0.0220
-5 1 7 0.0405
5 -1 -7 0.0405
-1 -7 -6 0.0377
1 7 6 0.0377
3 -7 1 0.0394
-3 7 -1 0.0394
-4 -2 -9 0.0459
4 2 9 0.0459

_exptl_crystal_size_max          0.115
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.044
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0008 -0.9889 15.0140 -0.2488 -0.8221 0.5048
-0.0008 0.9889 -15.0140 0.2488 0.8221 -0.5048
-4.9983 1.0100 7.0232 -0.1811 -0.8291 -0.5656
4.9983 -1.0100 -7.0232 0.1811 0.8291 0.5656
-1.0008 -7.0034 -5.9839 0.9582 0.0022 -0.0873
1.0008 7.0034 5.9839 -0.9582 -0.0022 0.0873
2.9986 -7.0021 1.0054 0.7083 0.0256 0.7307
-2.9986 7.0021 -1.0054 -0.7083 -0.0256 -0.7307
-3.9998 -2.0027 -8.9861 0.5248 0.0204 -0.8090
3.9998 2.0027 8.9861 -0.5248 -0.0204 0.8090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17380
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.665
_diffrn_reflns_theta_min         3.782
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -3.00   1.00    5.00    --  -41.65 125.00   0.00   93
  2  ω   -114.00 -14.00   1.00    5.00    --  -41.65 -57.00 -90.00  100
  3  ω     15.00  99.00   1.00    5.00    --   41.65  57.00-120.00   84
  4  ω     17.00 116.00   1.00    5.00    --   41.65  37.00-180.00   99
  5  ω     80.00 116.00   1.00   27.00    --  112.00-111.00   0.00   36
  6  ω     36.00 115.00   1.00   27.00    --  112.00-111.00-180.00   79
  7  ω     50.00 138.00   1.00   27.00    --  112.00 -77.00   0.00   88
  8  ω     88.00 168.00   1.00   27.00    --  112.00  45.00  30.00   80
  9  ω     43.00 137.00   1.00   27.00    --  112.00 -61.00-120.00   94
 10  ω     45.00  71.00   1.00   27.00    --  112.00-111.00   0.00   26
 11  ω     37.00 114.00   1.00   27.00    --  112.00-111.00 -90.00   77
 12  ω     36.00 140.00   1.00   27.00    --  112.00 -30.00   0.00  104
 13  ω    104.00 178.00   1.00   27.00    --  112.00 111.00 -30.00   74
 14  ω     52.00 165.00   1.00   27.00    --  112.00 -15.00-180.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0204521000
_diffrn_orient_matrix_UB_12      -0.1133595000
_diffrn_orient_matrix_UB_13      -0.0240368000
_diffrn_orient_matrix_UB_21      0.0979845000
_diffrn_orient_matrix_UB_22      0.0307391000
_diffrn_orient_matrix_UB_23      -0.0527343000
_diffrn_orient_matrix_UB_31      0.1498864000
_diffrn_orient_matrix_UB_32      -0.0356737000
_diffrn_orient_matrix_UB_33      0.0312634000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4643
_reflns_number_total             5197
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.2(5)
 -0.2(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25),
  C28(H28), C29(H29), C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C37(H37)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1862(2) 0.70808(16) 0.54804(8) 0.0284(4) Uani 1 1 d . . . . .
N7 N 0.8993(2) 0.91198(14) 0.64529(8) 0.0229(4) Uani 1 1 d . . . . .
C2 C 1.0312(3) 0.69399(17) 0.55141(9) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.9875 0.6374 0.5313 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9316(3) 0.75836(16) 0.58293(9) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.8248 0.7446 0.5842 0.028 Uiso 1 1 calc R . . . .
C4 C 0.9952(2) 0.84390(16) 0.61266(9) 0.0217(4) Uani 1 1 d . . . . .
C5 C 1.1560(3) 0.86105(18) 0.60923(10) 0.0255(4) Uani 1 1 d . . . . .
H5 H 1.2024 0.9179 0.6283 0.031 Uiso 1 1 calc R . . . .
C6 C 1.2449(3) 0.79134(19) 0.57679(10) 0.0282(5) Uani 1 1 d . . . . .
H6 H 1.3522 0.8031 0.5748 0.034 Uiso 1 1 calc R . . . .
C8 C 0.7581(2) 0.95758(15) 0.62756(9) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.6845(3) 0.95253(16) 0.57444(10) 0.0240(4) Uani 1 1 d . . . . .
H9 H 0.7266 0.9134 0.5444 0.029 Uiso 1 1 calc R . . . .
C10 C 0.5453(3) 1.00879(17) 0.56843(10) 0.0279(4) Uani 1 1 d . . . . .
H10 H 0.4934 1.0072 0.5335 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4814(3) 1.06759(18) 0.61338(11) 0.0300(5) Uani 1 1 d . . . . .
H11 H 0.3877 1.1038 0.6080 0.036 Uiso 1 1 calc R . . . .
C12 C 0.5558(3) 1.07269(17) 0.66589(10) 0.0275(4) Uani 1 1 d . . . . .
H12 H 0.5127 1.1118 0.6958 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6965(3) 1.01813(16) 0.67312(9) 0.0229(4) Uani 1 1 d . . . . .
C14 C 0.8035(3) 1.00764(16) 0.72063(9) 0.0237(4) Uani 1 1 d . . . . .
C15 C 0.8032(3) 1.04774(18) 0.77673(10) 0.0280(5) Uani 1 1 d . . . . .
H15 H 0.7229 1.0918 0.7893 0.034 Uiso 1 1 calc R . . . .
C16 C 0.9246(3) 1.02032(19) 0.81273(9) 0.0310(5) Uani 1 1 d . . . . .
H16 H 0.9266 1.0469 0.8499 0.037 Uiso 1 1 calc R . . . .
C17 C 1.0447(3) 0.95297(19) 0.79406(10) 0.0306(5) Uani 1 1 d . . . . .
H17 H 1.1243 0.9349 0.8194 0.037 Uiso 1 1 calc R . . . .
C18 C 1.0484(3) 0.91249(18) 0.73879(9) 0.0268(4) Uani 1 1 d . . . . .
H18 H 1.1283 0.8677 0.7267 0.032 Uiso 1 1 calc R . . . .
C19 C 0.9267(3) 0.94205(16) 0.70222(9) 0.0229(4) Uani 1 1 d . . . . .
N20 N 0.7088(2) 0.53708(17) 0.54109(9) 0.0348(5) Uani 1 1 d . . . . .
N26 N 0.3738(2) 0.35405(14) 0.62987(8) 0.0226(4) Uani 1 1 d . . . . .
C21 C 0.7474(3) 0.4480(2) 0.56941(10) 0.0314(5) Uani 1 1 d . . . . .
H21 H 0.8518 0.4272 0.5691 0.038 Uiso 1 1 calc R . . . .
C22 C 0.6420(3) 0.38487(18) 0.59907(10) 0.0259(4) Uani 1 1 d . . . . .
H22 H 0.6749 0.3235 0.6178 0.031 Uiso 1 1 calc R . . . .
C23 C 0.4858(2) 0.41553(16) 0.60010(9) 0.0219(4) Uani 1 1 d . . . . .
C24 C 0.4426(3) 0.50731(18) 0.57083(10) 0.0281(5) Uani 1 1 d . . . . .
H24 H 0.3391 0.5300 0.5705 0.034 Uiso 1 1 calc R . . . .
C25 C 0.5566(3) 0.56395(19) 0.54224(11) 0.0333(5) Uani 1 1 d . . . . .
H25 H 0.5262 0.6248 0.5224 0.040 Uiso 1 1 calc R . . . .
C27 C 0.3875(3) 0.31837(17) 0.68633(9) 0.0236(4) Uani 1 1 d . . . . .
C28 C 0.5020(3) 0.34146(18) 0.72662(10) 0.0271(5) Uani 1 1 d . . . . .
H28 H 0.5845 0.3871 0.7182 0.033 Uiso 1 1 calc R . . . .
C29 C 0.4886(3) 0.29359(19) 0.78018(10) 0.0301(5) Uani 1 1 d . . . . .
H29 H 0.5642 0.3067 0.8079 0.036 Uiso 1 1 calc R . . . .
C30 C 0.3628(3) 0.22600(19) 0.79299(10) 0.0331(5) Uani 1 1 d . . . . .
H30 H 0.3571 0.1943 0.8289 0.040 Uiso 1 1 calc R . . . .
C31 C 0.2474(3) 0.20570(18) 0.75325(10) 0.0300(5) Uani 1 1 d . . . . .
H31 H 0.1632 0.1620 0.7624 0.036 Uiso 1 1 calc R . . . .
C32 C 0.2592(3) 0.25206(16) 0.69894(9) 0.0243(4) Uani 1 1 d . . . . .
C33 C 0.1647(3) 0.24651(16) 0.64777(10) 0.0244(4) Uani 1 1 d . . . . .
C34 C 0.0291(3) 0.19078(17) 0.63359(11) 0.0309(5) Uani 1 1 d . . . . .
H34 H -0.0221 0.1497 0.6609 0.037 Uiso 1 1 calc R . . . .
C35 C -0.0283(3) 0.19742(19) 0.57843(12) 0.0341(5) Uani 1 1 d . . . . .
H35 H -0.1179 0.1597 0.5685 0.041 Uiso 1 1 calc R . . . .
C36 C 0.0470(3) 0.26037(19) 0.53731(11) 0.0320(5) Uani 1 1 d . . . . .
H36 H 0.0063 0.2637 0.5005 0.038 Uiso 1 1 calc R . . . .
C37 C 0.1816(3) 0.31820(17) 0.55030(10) 0.0267(4) Uani 1 1 d . . . . .
H37 H 0.2311 0.3602 0.5230 0.032 Uiso 1 1 calc R . . . .
C38 C 0.2389(2) 0.31030(16) 0.60620(9) 0.0230(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.340(3) . ?
N1 C6 1.340(3) . ?
N7 C4 1.409(3) . ?
N7 C8 1.399(3) . ?
N7 C19 1.403(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.394(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.393(3) . ?
C8 C13 1.410(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(3) . ?
C13 C14 1.445(3) . ?
C14 C15 1.404(3) . ?
C14 C19 1.405(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.400(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.397(3) . ?
N20 C21 1.341(3) . ?
N20 C25 1.345(3) . ?
N26 C23 1.413(3) . ?
N26 C27 1.399(3) . ?
N26 C38 1.392(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(3) . ?
C23 C24 1.390(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.380(3) . ?
C25 H25 0.9300 . ?
C27 C28 1.389(3) . ?
C27 C32 1.409(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.393(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.402(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.379(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.400(3) . ?
C32 C33 1.445(3) . ?
C33 C34 1.394(3) . ?
C33 C38 1.410(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.382(4) . ?
C35 H35 0.9300 . ?
C35 C36 1.401(4) . ?
C36 H36 0.9300 . ?
C36 C37 1.394(3) . ?
C37 H37 0.9300 . ?
C37 C38 1.399(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

C2 N1 C6 116.4(2) . . ?
C8 N7 C4 126.18(18) . . ?
C8 N7 C19 108.36(17) . . ?
C19 N7 C4 125.42(18) . . ?
N1 C2 H2 117.9 . . ?
N1 C2 C3 124.2(2) . . ?
C3 C2 H2 117.9 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.5(2) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 N7 120.80(19) . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 N7 120.8(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 124.2(2) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
N7 C8 C13 108.61(18) . . ?
C9 C8 N7 129.4(2) . . ?
C9 C8 C13 121.9(2) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.5 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 C14 107.15(19) . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 C14 133.2(2) . . ?
C15 C14 C13 133.1(2) . . ?
C19 C14 C13 107.03(19) . . ?
C19 C14 C15 119.8(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.8(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 121.5 . . ?
C17 C18 C19 117.1(2) . . ?
C19 C18 H18 121.5 . . ?
N7 C19 C14 108.85(19) . . ?
C18 C19 N7 129.3(2) . . ?
C18 C19 C14 121.8(2) . . ?
C21 N20 C25 116.0(2) . . ?
C27 N26 C23 125.62(19) . . ?
C38 N26 C23 125.56(19) . . ?
C38 N26 C27 108.55(17) . . ?
N20 C21 H21 117.9 . . ?
N20 C21 C22 124.3(2) . . ?
C22 C21 H21 117.9 . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.4(2) . . ?
C23 C22 H22 120.8 . . ?
C22 C23 N26 120.56(19) . . ?
C22 C23 C24 118.5(2) . . ?
C24 C23 N26 121.0(2) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.5(2) . . ?
C25 C24 H24 120.7 . . ?
N20 C25 C24 124.4(2) . . ?
N20 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
N26 C27 C32 108.75(19) . . ?
C28 C27 N26 129.2(2) . . ?
C28 C27 C32 122.0(2) . . ?
C27 C28 H28 121.3 . . ?
C27 C28 C29 117.4(2) . . ?
C29 C28 H28 121.3 . . ?
C28 C29 H29 119.5 . . ?
C28 C29 C30 121.1(2) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.1(2) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 120.6 . . ?
C30 C31 C32 118.8(2) . . ?
C32 C31 H31 120.6 . . ?
C27 C32 C33 106.92(19) . . ?
C31 C32 C27 119.4(2) . . ?
C31 C32 C33 133.6(2) . . ?
C34 C33 C32 133.3(2) . . ?
C34 C33 C38 119.7(2) . . ?
C38 C33 C32 106.92(19) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 C33 119.1(2) . . ?
C35 C34 H34 120.4 . . ?
C34 C35 H35 119.6 . . ?
C34 C35 C36 120.7(2) . . ?
C36 C35 H35 119.6 . . ?
C35 C36 H36 119.2 . . ?
C37 C36 C35 121.6(2) . . ?
C37 C36 H36 119.2 . . ?
C36 C37 H37 121.4 . . ?
C36 C37 C38 117.1(2) . . ?
C38 C37 H37 121.4 . . ?
N26 C38 C33 108.87(19) . . ?
N26 C38 C37 129.3(2) . . ?
C37 C38 C33 121.7(2) . . ?


_ins_header                      
;
TITL OHI-088_scale in P2(1)2(1)2(1) 
REM P2(1)2(1)2(1) (#19 in standard setting)
CELL 1.54184   8.551408  12.556489  23.372982  90.0000  90.0000  90.0000
ZERR    7.00   0.000153   0.000195   0.000476   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N
UNIT 119.00 84.00 14.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.266
_oxdiff_exptl_absorpt_empirical_full_min 0.788
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.2(5)
2 -0.2(5)

####################################################################### 
# 
# 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_L6
_database_code_depnum_ccdc_archive 'CCDC 2080284'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 N O'
_chemical_formula_sum            'C25 H17 N O'
_chemical_formula_weight         347.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.7787(3)
_cell_length_b                   10.2421(2)
_cell_length_c                   14.8133(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.6600(10)
_cell_angle_gamma                90
_cell_volume                     1775.81(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4464
_cell_measurement_temperature    170
_cell_measurement_theta_max      28.700
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0788 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.9083.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13317
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.492
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3128
_reflns_number_total             3912
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+0.8527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O21 O 0.01958(9) 0.34244(12) 0.52407(9) 0.0384(3) Uani 1 1 d . . . . .
N10 N 0.49399(10) 0.53769(12) 0.85246(9) 0.0250(3) Uani 1 1 d . . . . .
C1 C 0.56476(13) 0.81853(15) 1.07088(12) 0.0301(4) Uani 1 1 d . . . . .
H1 H 0.5837 0.8791 1.1236 0.036 Uiso 1 1 calc R . . . .
C2 C 0.64436(13) 0.72739(14) 1.07119(11) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.7185 0.7259 1.1230 0.031 Uiso 1 1 calc R . . . .
C3 C 0.61414(12) 0.63726(14) 0.99411(11) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.67580(12) 0.53281(14) 0.97130(11) 0.0236(3) Uani 1 1 d . . . . .
C5 C 0.78732(13) 0.48563(16) 1.01877(12) 0.0293(3) Uani 1 1 d . . . . .
H5 H 0.8401 0.5273 1.0764 0.035 Uiso 1 1 calc R . . . .
C6 C 0.81949(14) 0.37708(17) 0.98026(12) 0.0339(4) Uani 1 1 d . . . . .
H6 H 0.8954 0.3448 1.0109 0.041 Uiso 1 1 calc R . . . .
C7 C 0.74109(14) 0.31471(16) 0.89662(12) 0.0322(4) Uani 1 1 d . . . . .
H7 H 0.7642 0.2389 0.8726 0.039 Uiso 1 1 calc R . . . .
C8 C 0.63051(13) 0.36044(15) 0.84779(12) 0.0282(3) Uani 1 1 d . . . . .
H8 H 0.5778 0.3174 0.7909 0.034 Uiso 1 1 calc R . . . .
C9 C 0.59936(12) 0.47187(14) 0.88508(11) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.50348(12) 0.63867(14) 0.91894(11) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.42409(13) 0.73378(15) 0.91697(12) 0.0280(3) Uani 1 1 d . . . . .
H12 H 0.3504 0.7372 0.8647 0.034 Uiso 1 1 calc R . . . .
C13 C 0.45643(13) 0.82263(15) 0.99363(12) 0.0314(4) Uani 1 1 d . . . . .
H13 H 0.4038 0.8880 0.9938 0.038 Uiso 1 1 calc R . . . .
C14 C 0.39592(12) 0.50594(14) 0.76695(11) 0.0233(3) Uani 1 1 d . . . . .
C15 C 0.40738(12) 0.46898(14) 0.68123(11) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.4809 0.4679 0.6794 0.030 Uiso 1 1 calc R . . . .
C16 C 0.31261(13) 0.43377(14) 0.59850(11) 0.0256(3) Uani 1 1 d . . . . .
H16 H 0.3217 0.4083 0.5404 0.031 Uiso 1 1 calc R . . . .
C17 C 0.20358(12) 0.43508(14) 0.59911(11) 0.0250(3) Uani 1 1 d . . . . .
C18 C 0.19254(12) 0.47281(14) 0.68539(11) 0.0256(3) Uani 1 1 d . . . . .
H18 H 0.1191 0.4738 0.6872 0.031 Uiso 1 1 calc R . . . .
C19 C 0.28697(12) 0.50874(15) 0.76810(11) 0.0262(3) Uani 1 1 d . . . . .
H19 H 0.2780 0.5354 0.8260 0.031 Uiso 1 1 calc R . . . .
C20 C 0.10139(13) 0.38987(15) 0.51248(12) 0.0281(3) Uani 1 1 d . . . . .
C22 C 0.10030(12) 0.40007(15) 0.41150(12) 0.0277(3) Uani 1 1 d . . . . .
C23 C 0.15137(13) 0.50396(16) 0.38360(12) 0.0312(4) Uani 1 1 d . . . . .
H23 H 0.1886 0.5710 0.4296 0.037 Uiso 1 1 calc R . . . .
C24 C 0.14800(14) 0.50984(19) 0.28902(13) 0.0400(4) Uani 1 1 d . . . . .
H24 H 0.1825 0.5812 0.2704 0.048 Uiso 1 1 calc R . . . .
C25 C 0.09441(15) 0.4121(2) 0.22133(13) 0.0444(5) Uani 1 1 d . . . . .
H25 H 0.0943 0.4150 0.1572 0.053 Uiso 1 1 calc R . . . .
C26 C 0.04092(15) 0.30983(19) 0.24770(13) 0.0420(4) Uani 1 1 d . . . . .
H26 H 0.0028 0.2437 0.2011 0.050 Uiso 1 1 calc R . . . .
C27 C 0.04327(13) 0.30438(16) 0.34159(12) 0.0342(4) Uani 1 1 d . . . . .
H27 H 0.0057 0.2349 0.3590 0.041 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O21 C20 1.2257(18) . ?
N10 C9 1.4067(18) . ?
N10 C11 1.3995(19) . ?
N10 C14 1.4166(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(2) . ?
C1 C13 1.399(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(2) . ?
C3 C4 1.447(2) . ?
C3 C11 1.406(2) . ?
C4 C5 1.398(2) . ?
C4 C9 1.405(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.397(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(2) . ?
C11 C12 1.398(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 C19 1.399(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(2) . ?
C17 C18 1.395(2) . ?
C17 C20 1.490(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(2) . ?
C19 H19 0.9500 . ?
C20 C22 1.494(2) . ?
C22 C23 1.395(2) . ?
C22 C27 1.399(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(2) . ?
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
C9 N10 C14 125.35(12) . . ?
C11 N10 C9 108.17(12) . . ?
C11 N10 C14 126.48(12) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C13 120.63(15) . . ?
C13 C1 H1 119.7 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.88(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 132.98(14) . . ?
C2 C3 C11 120.06(13) . . ?
C11 C3 C4 106.96(13) . . ?
C5 C4 C3 132.75(14) . . ?
C5 C4 C9 120.01(14) . . ?
C9 C4 C3 107.20(12) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.77(15) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.44(15) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.79(15) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.62(14) . . ?
C9 C8 H8 121.2 . . ?
C4 C9 N10 108.65(12) . . ?
C8 C9 N10 129.98(14) . . ?
C8 C9 C4 121.28(13) . . ?
N10 C11 C3 108.99(12) . . ?
C12 C11 N10 130.01(14) . . ?
C12 C11 C3 120.97(14) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.78(14) . . ?
C13 C12 H12 121.1 . . ?
C1 C13 H13 119.2 . . ?
C12 C13 C1 121.58(14) . . ?
C12 C13 H13 119.2 . . ?
C15 C14 N10 120.03(13) . . ?
C15 C14 C19 119.18(13) . . ?
C19 C14 N10 120.78(13) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.41(14) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.90(14) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C20 121.53(14) . . ?
C18 C17 C16 118.44(13) . . ?
C18 C17 C20 119.93(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.87(14) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.21(14) . . ?
C18 C19 H19 119.9 . . ?
O21 C20 C17 120.29(15) . . ?
O21 C20 C22 120.14(14) . . ?
C17 C20 C22 119.56(13) . . ?
C23 C22 C20 122.17(14) . . ?
C23 C22 C27 118.79(15) . . ?
C27 C22 C20 119.00(14) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.29(16) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.35(17) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.77(18) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.97(17) . . ?
C27 C26 H26 120.0 . . ?
C22 C27 H27 119.6 . . ?
C26 C27 C22 120.78(17) . . ?
C26 C27 H27 119.6 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L4He
_database_code_depnum_ccdc_archive 'CCDC 2080294'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7

# start Validation Reply Form
_vrf_PLAT353_L4He                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2, C2 H Br2 O2'
_chemical_formula_sum            'C25 H18 Br2 N2 O2'
_chemical_formula_weight         538.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.9258(3)
_cell_length_b                   10.6675(2)
_cell_length_c                   21.9071(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4189.15(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.697
_shelx_estimated_absorpt_T_min   0.246
_exptl_absorpt_coefficient_mu    3.896
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.5579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0997 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.7481.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8728
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         2.272
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3611
_reflns_number_total             4614
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+5.7203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0870
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C76(H76)
2.b Aromatic/amide H refined with riding coordinates:
 N23(H23), C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br73 Br 0.33045(2) 0.56404(3) 0.68836(2) 0.03786(10) Uani 1 1 d . . . . .
Br74 Br 0.31379(2) 0.81546(3) 0.76278(2) 0.03560(10) Uani 1 1 d . . . . .
O71 O 0.32050(12) 0.8572(2) 0.62289(11) 0.0416(6) Uani 1 1 d . . . . .
O72 O 0.43974(14) 0.7979(2) 0.61624(12) 0.0464(6) Uani 1 1 d . . . . .
N10 N 0.43246(13) 1.7562(2) 0.39110(12) 0.0246(5) Uani 1 1 d . . . . .
N23 N 0.35539(14) 1.0631(2) 0.56572(12) 0.0314(6) Uani 1 1 d . . . . .
H23 H 0.3437 0.9784 0.5871 0.038 Uiso 1 1 calc R . . . .
C1 C 0.31122(18) 2.0873(3) 0.38315(16) 0.0341(7) Uani 1 1 d . . . . .
H1 H 0.2860 2.1632 0.3803 0.041 Uiso 1 1 calc R . . . .
C2 C 0.37683(17) 2.0701(3) 0.35147(15) 0.0311(7) Uani 1 1 d . . . . .
H2 H 0.3958 2.1337 0.3269 0.037 Uiso 1 1 calc R . . . .
C3 C 0.41452(16) 1.9558(3) 0.35672(14) 0.0249(6) Uani 1 1 d . . . . .
C4 C 0.48044(16) 1.9067(3) 0.32808(14) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.53206(17) 1.9550(3) 0.28692(15) 0.0304(7) Uani 1 1 d . . . . .
H5 H 0.5266 2.0360 0.2719 0.036 Uiso 1 1 calc R . . . .
C6 C 0.59152(18) 1.8817(3) 0.26842(15) 0.0331(7) Uani 1 1 d . . . . .
H6 H 0.6260 1.9134 0.2407 0.040 Uiso 1 1 calc R . . . .
C7 C 0.60004(17) 1.7606(3) 0.29102(15) 0.0320(7) Uani 1 1 d . . . . .
H7 H 0.6407 1.7130 0.2783 0.038 Uiso 1 1 calc R . . . .
C8 C 0.54980(16) 1.7089(3) 0.33188(15) 0.0276(7) Uani 1 1 d . . . . .
H8 H 0.5560 1.6279 0.3468 0.033 Uiso 1 1 calc R . . . .
C9 C 0.48965(16) 1.7829(3) 0.34984(13) 0.0240(6) Uani 1 1 d . . . . .
C11 C 0.38563(15) 1.8621(3) 0.39517(14) 0.0240(6) Uani 1 1 d . . . . .
C12 C 0.31915(16) 1.8775(3) 0.42677(15) 0.0289(7) Uani 1 1 d . . . . .
H12 H 0.3000 1.8146 0.4517 0.035 Uiso 1 1 calc R . . . .
C13 C 0.28253(17) 1.9911(3) 0.41949(16) 0.0347(7) Uani 1 1 d . . . . .
H13 H 0.2374 2.0036 0.4395 0.042 Uiso 1 1 calc R . . . .
C14 C 0.42184(15) 1.6393(3) 0.42110(14) 0.0243(6) Uani 1 1 d . . . . .
C15 C 0.43043(16) 1.5283(3) 0.38868(14) 0.0256(6) Uani 1 1 d . . . . .
H15 H 0.4419 1.5309 0.3473 0.031 Uiso 1 1 calc R . . . .
C16 C 0.42197(16) 1.4138(3) 0.41761(14) 0.0267(6) Uani 1 1 d . . . . .
H16 H 0.4296 1.3400 0.3959 0.032 Uiso 1 1 calc R . . . .
C17 C 0.40206(15) 1.4084(3) 0.47911(14) 0.0249(6) Uani 1 1 d . . . . .
C18 C 0.39374(15) 1.5208(3) 0.51126(14) 0.0268(6) Uani 1 1 d . . . . .
H18 H 0.3809 1.5184 0.5524 0.032 Uiso 1 1 calc R . . . .
C19 C 0.40427(15) 1.6356(3) 0.48307(14) 0.0267(6) Uani 1 1 d . . . . .
H19 H 0.3997 1.7096 0.5052 0.032 Uiso 1 1 calc R . . . .
C20 C 0.38689(16) 1.2871(3) 0.50934(14) 0.0256(6) Uani 1 1 d . . . . .
C21 C 0.42851(16) 1.1795(3) 0.49640(14) 0.0279(6) Uani 1 1 d . . . . .
H21 H 0.4671 1.1823 0.4681 0.033 Uiso 1 1 calc R . . . .
C22 C 0.41170(16) 1.0696(3) 0.52599(15) 0.0301(7) Uani 1 1 d . . . . .
H22 H 0.4401 0.9984 0.5182 0.036 Uiso 1 1 calc R . . . .
C24 C 0.31419(17) 1.1631(3) 0.57829(16) 0.0340(7) Uani 1 1 d . . . . .
H24 H 0.2751 1.1563 0.6060 0.041 Uiso 1 1 calc R . . . .
C25 C 0.32839(17) 1.2768(3) 0.55082(15) 0.0323(7) Uani 1 1 d . . . . .
H25 H 0.2991 1.3463 0.5599 0.039 Uiso 1 1 calc R . . . .
C75 C 0.37844(18) 0.8018(3) 0.64110(15) 0.0307(7) Uani 1 1 d . . . . .
C76 C 0.37310(16) 0.7298(3) 0.70196(14) 0.0288(7) Uani 1 1 d . . . . .
H76 H 0.4237 0.7191 0.7182 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br73 C76 1.949(3) . ?
Br74 C76 1.934(3) . ?
O71 C75 1.259(4) . ?
O72 C75 1.227(4) . ?
N10 C9 1.396(4) . ?
N10 C11 1.410(3) . ?
N10 C14 1.422(3) . ?
N23 H23 1.0400 . ?
N23 C22 1.335(4) . ?
N23 C24 1.326(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(5) . ?
C1 C13 1.397(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.399(4) . ?
C3 C4 1.437(4) . ?
C3 C11 1.406(4) . ?
C4 C5 1.391(4) . ?
C4 C9 1.413(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.392(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(4) . ?
C11 C12 1.388(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(4) . ?
C14 C19 1.394(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.395(4) . ?
C17 C18 1.398(4) . ?
C17 C20 1.479(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.398(4) . ?
C20 C25 1.392(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.378(4) . ?
C25 H25 0.9300 . ?
C75 C76 1.542(4) . ?
C76 H76 0.9800 . ?

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
C9 N10 C11 108.3(2) . . ?
C9 N10 C14 125.2(2) . . ?
C11 N10 C14 126.4(2) . . ?
C22 N23 H23 119.5 . . ?
C24 N23 H23 119.5 . . ?
C24 N23 C22 121.0(3) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C13 120.2(3) . . ?
C13 C1 H1 119.9 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.1(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 132.8(3) . . ?
C2 C3 C11 119.4(3) . . ?
C11 C3 C4 107.8(2) . . ?
C5 C4 C3 134.1(3) . . ?
C5 C4 C9 119.1(3) . . ?
C9 C4 C3 106.8(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.3 . . ?
C7 C8 C9 117.4(3) . . ?
C9 C8 H8 121.3 . . ?
N10 C9 C4 108.9(2) . . ?
C8 C9 N10 129.4(3) . . ?
C8 C9 C4 121.6(3) . . ?
C3 C11 N10 108.2(2) . . ?
C12 C11 N10 129.6(3) . . ?
C12 C11 C3 122.1(3) . . ?
C11 C12 H12 121.6 . . ?
C13 C12 C11 116.9(3) . . ?
C13 C12 H12 121.6 . . ?
C1 C13 H13 118.9 . . ?
C12 C13 C1 122.2(3) . . ?
C12 C13 H13 118.9 . . ?
C15 C14 N10 119.7(3) . . ?
C15 C14 C19 119.9(3) . . ?
C19 C14 N10 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 C20 121.0(3) . . ?
C18 C17 C20 120.3(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.3(3) . . ?
C18 C19 H19 120.3 . . ?
C21 C20 C17 122.0(3) . . ?
C25 C20 C17 120.0(3) . . ?
C25 C20 C21 118.0(3) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(3) . . ?
C22 C21 H21 120.4 . . ?
N23 C22 C21 121.2(3) . . ?
N23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
N23 C24 H24 119.5 . . ?
N23 C24 C25 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.6(3) . . ?
C24 C25 H25 120.2 . . ?
O71 C75 C76 117.2(3) . . ?
O72 C75 O71 127.9(3) . . ?
O72 C75 C76 115.0(3) . . ?
Br73 C76 H76 108.3 . . ?
Br74 C76 Br73 108.57(14) . . ?
Br74 C76 H76 108.3 . . ?
C75 C76 Br73 110.1(2) . . ?
C75 C76 Br74 113.2(2) . . ?
C75 C76 H76 108.3 . . ?

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
O71 C75 C76 Br73 82.9(3) . . . . ?
O71 C75 C76 Br74 -38.9(3) . . . . ?
O72 C75 C76 Br73 -97.2(3) . . . . ?
O72 C75 C76 Br74 141.0(2) . . . . ?
N10 C11 C12 C13 -176.3(3) . . . . ?
N10 C14 C15 C16 178.5(3) . . . . ?
N10 C14 C19 C18 179.6(2) . . . . ?
N23 C24 C25 C20 -0.1(5) . . . . ?
C1 C2 C3 C4 176.3(3) . . . . ?
C1 C2 C3 C11 -1.4(4) . . . . ?
C2 C1 C13 C12 2.0(5) . . . . ?
C2 C3 C4 C5 2.8(6) . . . . ?
C2 C3 C4 C9 -177.6(3) . . . . ?
C2 C3 C11 N10 178.5(3) . . . . ?
C2 C3 C11 C12 2.3(4) . . . . ?
C3 C4 C5 C6 179.2(3) . . . . ?
C3 C4 C9 N10 -0.8(3) . . . . ?
C3 C4 C9 C8 -178.6(3) . . . . ?
C3 C11 C12 C13 -1.0(4) . . . . ?
C4 C3 C11 N10 0.2(3) . . . . ?
C4 C3 C11 C12 -176.0(3) . . . . ?
C4 C5 C6 C7 -0.4(5) . . . . ?
C5 C4 C9 N10 178.9(3) . . . . ?
C5 C4 C9 C8 1.1(4) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 N10 -178.2(3) . . . . ?
C7 C8 C9 C4 -0.9(4) . . . . ?
C9 N10 C11 C3 -0.7(3) . . . . ?
C9 N10 C11 C12 175.1(3) . . . . ?
C9 N10 C14 C15 -42.4(4) . . . . ?
C9 N10 C14 C19 136.4(3) . . . . ?
C9 C4 C5 C6 -0.4(5) . . . . ?
C11 N10 C9 C4 1.0(3) . . . . ?
C11 N10 C9 C8 178.5(3) . . . . ?
C11 N10 C14 C15 134.1(3) . . . . ?
C11 N10 C14 C19 -47.1(4) . . . . ?
C11 C3 C4 C5 -179.3(3) . . . . ?
C11 C3 C4 C9 0.4(3) . . . . ?
C11 C12 C13 C1 -1.2(5) . . . . ?
C13 C1 C2 C3 -0.7(5) . . . . ?
C14 N10 C9 C4 178.0(3) . . . . ?
C14 N10 C9 C8 -4.4(5) . . . . ?
C14 N10 C11 C3 -177.7(3) . . . . ?
C14 N10 C11 C12 -1.9(5) . . . . ?
C14 C15 C16 C17 2.3(4) . . . . ?
C15 C14 C19 C18 -1.6(4) . . . . ?
C15 C16 C17 C18 -2.4(4) . . . . ?
C15 C16 C17 C20 175.0(3) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C16 C17 C20 C21 38.1(4) . . . . ?
C16 C17 C20 C25 -140.0(3) . . . . ?
C17 C18 C19 C14 1.5(4) . . . . ?
C17 C20 C21 C22 -180.0(3) . . . . ?
C17 C20 C25 C24 179.3(3) . . . . ?
C18 C17 C20 C21 -144.4(3) . . . . ?
C18 C17 C20 C25 37.4(4) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
C20 C17 C18 C19 -177.0(3) . . . . ?
C20 C21 C22 N23 1.6(5) . . . . ?
C21 C20 C25 C24 1.1(5) . . . . ?
C22 N23 C24 C25 -0.2(5) . . . . ?
C24 N23 C22 C21 -0.6(5) . . . . ?
C25 C20 C21 C22 -1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L3Ha
_database_code_depnum_ccdc_archive 'CCDC 2080289'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_STRVA01_L3Ha                
;
PROBLEM: Flack test results are meaningless.
RESPONSE: A light-atom structure was measured 
using Mo radiation and therefore the error on 
the Flack parameter was bad.  
;
_vrf_PLAT029_L3Ha                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.976 Why?  
RESPONSE: ...
;
_vrf_PLAT244_L3Ha                
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C73 Check 
RESPONSE: Due to a disordered anion.
;
_vrf_PLAT250_L3Ha                
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: Due to a disordered anion.
;
_vrf_PLAT340_L3Ha                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00439 Ang.  
RESPONSE: Due to a disordered anion.
;
_vrf_PLAT353_L3Ha                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N17      - H17      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N2, C2 F3 O2, H2 O'
_chemical_formula_sum            'C19 H15 F3 N2 O3'
_chemical_formula_weight         376.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.0779(7)
_cell_length_b                   4.9534(2)
_cell_length_c                   13.5651(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.798(2)
_cell_angle_gamma                90
_cell_volume                     877.70(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0825 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.6948.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7548
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.503
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                3056
_reflns_number_total             3522
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.2465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(14)
 0.2(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 F78-F80
 -2 with sigma of 0.02
4. Rigid body (RIGU) restrains
 O71, O72, C73, C74, F75, F76, F77, F78, F79, F80
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(F78)=Sof(F79)=Sof(F80)=1-FVAR(1)
 Sof(F75)=Sof(F76)=Sof(F77)=FVAR(1)
6.a Free rotating group:
 O91(H91A,H91B)
6.b Aromatic/amide H refined with riding coordinates:
 N17(H17), C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O71 O 0.10823(16) 0.9231(5) 0.43213(16) 0.0511(6) Uani 1 1 d . U . . .
O72 O 0.25829(18) 1.0743(8) 0.3880(2) 0.0878(12) Uani 1 1 d . U . . .
C73 C 0.1664(2) 1.0498(7) 0.3796(2) 0.0431(7) Uani 1 1 d . U . . .
C74 C 0.1091(3) 1.1952(9) 0.2939(3) 0.0562(9) Uani 1 1 d . U . . .
F75 F 0.1698(8) 1.434(3) 0.2729(14) 0.066(4) Uani 0.283(18) 1 d . U P A 1
F76 F 0.0227(13) 1.320(5) 0.3136(14) 0.060(3) Uani 0.283(18) 1 d . U P A 1
F77 F 0.0504(12) 0.980(4) 0.2371(13) 0.054(3) Uani 0.283(18) 1 d . U P A 1
F78 F 0.1670(4) 1.305(2) 0.2286(6) 0.094(3) Uani 0.717(18) 1 d D U P A 2
F79 F 0.0422(7) 1.3696(19) 0.3307(8) 0.086(2) Uani 0.717(18) 1 d . U P A 2
F80 F 0.0617(7) 1.045(2) 0.2319(7) 0.102(2) Uani 0.717(18) 1 d D U P A 2
O91 O 0.45732(17) 1.0098(5) 0.47015(18) 0.0459(5) Uani 1 1 d . . . . .
H91A H 0.3982 1.0355 0.4429 0.069 Uiso 1 1 d G . . . .
H91B H 0.4764 1.1654 0.4901 0.069 Uiso 1 1 d G . . . .
N5 N 0.30985(17) 0.1205(5) 0.79361(17) 0.0324(5) Uani 1 1 d . . . . .
N17 N 0.19325(18) 0.6029(5) 0.56567(18) 0.0358(6) Uani 1 1 d . . . . .
H17 H 0.1637 0.7255 0.5089 0.043 Uiso 1 1 calc R . . . .
C1 C 0.1784(3) -0.2495(8) 1.0302(3) 0.0544(9) Uani 1 1 d . . . . .
H1 H 0.1511 -0.3409 1.0846 0.065 Uiso 1 1 calc R . . . .
C2 C 0.1205(3) -0.0515(8) 0.9812(3) 0.0519(8) Uani 1 1 d . . . . .
H2 H 0.0550 -0.0069 1.0039 0.062 Uiso 1 1 calc R . . . .
C3 C 0.1562(2) 0.0829(7) 0.9000(2) 0.0429(7) Uani 1 1 d . . . . .
H3 H 0.1165 0.2182 0.8666 0.052 Uiso 1 1 calc R . . . .
C4 C 0.2525(2) 0.0114(6) 0.86953(19) 0.0344(6) Uani 1 1 d . . . . .
C6 C 0.4079(2) -0.0024(6) 0.79863(19) 0.0309(6) Uani 1 1 d . . . . .
C7 C 0.4894(2) 0.0278(6) 0.7374(2) 0.0365(6) Uani 1 1 d . . . . .
H7 H 0.4871 0.1545 0.6848 0.044 Uiso 1 1 calc R . . . .
C8 C 0.5748(2) -0.1358(7) 0.7567(2) 0.0419(7) Uani 1 1 d . . . . .
H8 H 0.6321 -0.1184 0.7168 0.050 Uiso 1 1 calc R . . . .
C9 C 0.5781(3) -0.3238(7) 0.8329(2) 0.0475(8) Uani 1 1 d . . . . .
H9 H 0.6375 -0.4323 0.8440 0.057 Uiso 1 1 calc R . . . .
C10 C 0.4971(3) -0.3548(7) 0.8920(2) 0.0427(8) Uani 1 1 d . . . . .
H10 H 0.4999 -0.4845 0.9437 0.051 Uiso 1 1 calc R . . . .
C11 C 0.4104(2) -0.1937(6) 0.8755(2) 0.0355(6) Uani 1 1 d . . . . .
C12 C 0.3131(2) -0.1834(6) 0.9209(2) 0.0367(7) Uani 1 1 d . . . . .
C13 C 0.2742(3) -0.3156(7) 1.0016(2) 0.0473(8) Uani 1 1 d . . . . .
H13 H 0.3136 -0.4496 1.0362 0.057 Uiso 1 1 calc R . . . .
C14 C 0.2711(2) 0.2837(5) 0.71685(19) 0.0291(6) Uani 1 1 d . . . . .
C15 C 0.1693(2) 0.2550(6) 0.6810(2) 0.0335(6) Uani 1 1 d . . . . .
H15 H 0.1260 0.1239 0.7085 0.040 Uiso 1 1 calc R . . . .
C16 C 0.1331(2) 0.4187(6) 0.6057(2) 0.0371(7) Uani 1 1 d . . . . .
H16 H 0.0641 0.4009 0.5815 0.045 Uiso 1 1 calc R . . . .
C18 C 0.2915(2) 0.6315(6) 0.5980(2) 0.0333(6) Uani 1 1 d . . . . .
H18 H 0.3332 0.7625 0.5682 0.040 Uiso 1 1 calc R . . . .
C19 C 0.3325(2) 0.4753(6) 0.67303(19) 0.0300(6) Uani 1 1 d . . . . .
H19 H 0.4021 0.4970 0.6951 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O71 C73 1.238(4) . ?
O72 C73 1.208(4) . ?
C73 C74 1.532(4) . ?
C74 F75 1.459(12) . ?
C74 F76 1.327(19) . ?
C74 F77 1.505(18) . ?
C74 F78 1.311(5) . ?
C74 F79 1.343(9) . ?
C74 F80 1.262(10) . ?
O91 H91A 0.8503 . ?
O91 H91B 0.8503 . ?
N5 C4 1.411(4) . ?
N5 C6 1.418(3) . ?
N5 C14 1.394(3) . ?
N17 H17 1.0400 . ?
N17 C16 1.337(4) . ?
N17 C18 1.345(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(5) . ?
C1 C13 1.370(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C12 1.412(4) . ?
C6 C7 1.391(4) . ?
C6 C11 1.409(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.393(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(4) . ?
C11 C12 1.441(5) . ?
C12 C13 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(4) . ?
C14 C19 1.395(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(4) . ?
C16 H16 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.367(4) . ?
C19 H19 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
O71 C73 C74 112.6(3) . . ?
O72 C73 O71 129.2(3) . . ?
O72 C73 C74 118.1(3) . . ?
F75 C74 C73 106.2(6) . . ?
F75 C74 F77 138.0(11) . . ?
F76 C74 C73 117.1(9) . . ?
F76 C74 F75 98.0(11) . . ?
F76 C74 F77 90.9(11) . . ?
F77 C74 C73 105.9(7) . . ?
F78 C74 C73 115.5(3) . . ?
F78 C74 F79 113.1(7) . . ?
F79 C74 C73 108.8(5) . . ?
F80 C74 C73 115.7(6) . . ?
F80 C74 F78 94.4(9) . . ?
F80 C74 F79 108.6(7) . . ?
H91A O91 H91B 104.4 . . ?
C4 N5 C6 108.2(2) . . ?
C14 N5 C4 125.5(2) . . ?
C14 N5 C6 125.4(2) . . ?
C16 N17 H17 119.6 . . ?
C16 N17 C18 120.7(3) . . ?
C18 N17 H17 119.6 . . ?
C2 C1 H1 119.4 . . ?
C13 C1 H1 119.4 . . ?
C13 C1 C2 121.2(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
N5 C4 C12 108.4(2) . . ?
C3 C4 N5 129.9(3) . . ?
C3 C4 C12 121.5(3) . . ?
C7 C6 N5 130.0(3) . . ?
C7 C6 C11 121.6(3) . . ?
C11 C6 N5 108.2(2) . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.1(3) . . ?
C8 C7 H7 121.4 . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.2(3) . . ?
C11 C10 H10 120.4 . . ?
C6 C11 C12 107.7(2) . . ?
C10 C11 C6 119.5(3) . . ?
C10 C11 C12 132.8(3) . . ?
C4 C12 C11 107.4(2) . . ?
C13 C12 C4 119.4(3) . . ?
C13 C12 C11 133.1(3) . . ?
C1 C13 C12 119.0(3) . . ?
C1 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N5 C14 C15 120.3(2) . . ?
N5 C14 C19 121.1(2) . . ?
C19 C14 C15 118.5(2) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 H15 120.5 . . ?
N17 C16 C15 121.2(3) . . ?
N17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
N17 C18 H18 119.4 . . ?
N17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 H19 120.3 . . ?
C18 C19 C14 119.3(2) . . ?
C18 C19 H19 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(14)
2 0.2(14)

####################################################################### 
# 
# 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_L4Ha
_database_code_depnum_ccdc_archive 'CCDC 2080290'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7

# start Validation Reply Form
_vrf_PLAT244_L4Ha                
;
PROBLEM: Low    'Solvent' Ueq as Compared to Neighbors of        C76 Check 
RESPONSE: This is caused by a disordered anion, which was 
modelled over two positions.
;
_vrf_PLAT250_L4Ha                
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.7 Note  
RESPONSE: This is caused by a disordered anion, which was 
modelled over two positions. 
;
_vrf_PLAT353_L4Ha                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2, C2 F3 O2'
_chemical_formula_sum            'C25 H17 F3 N2 O2'
_chemical_formula_weight         434.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6972(4)
_cell_length_b                   11.4158(4)
_cell_length_c                   19.0822(6)
_cell_angle_alpha                90
_cell_angle_beta                 118.604(2)
_cell_angle_gamma                90
_cell_volume                     3958.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    170
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0720 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.8596.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10345
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         2.107
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             4342
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4342
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0370P)²+7.6868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 C76, F73A, C77, F74B, F75A, F73B, F75B, F74A, O71, O72
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(F73B)=Sof(F74B)=Sof(F75B)=1-FVAR(1)
 Sof(F73A)=Sof(F74A)=Sof(F75A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N23(H23), C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F73A F 0.5049(5) 0.0631(12) 0.4393(6) 0.078(2) Uani 0.422(5) 1 d . U P A 2
F73B F 0.5295(3) 0.0611(8) 0.4380(4) 0.083(2) Uani 0.578(5) 1 d . U P A 1
F74A F 0.5475(3) 0.1080(6) 0.3576(4) 0.0901(19) Uani 0.422(5) 1 d . U P A 2
F74B F 0.4976(4) 0.0535(4) 0.3203(3) 0.1028(18) Uani 0.578(5) 1 d . U P A 1
F75A F 0.4420(3) 0.0435(5) 0.3032(4) 0.082(2) Uani 0.422(5) 1 d . U P A 2
F75B F 0.41863(17) 0.0269(3) 0.3582(3) 0.0712(14) Uani 0.578(5) 1 d . U P A 1
O71 O 0.39307(9) 0.24819(15) 0.30949(10) 0.0409(5) Uani 1 1 d . U . . .
O72 O 0.50647(9) 0.29743(19) 0.40404(12) 0.0521(5) Uani 1 1 d . U . . .
N10 N 0.20705(9) 1.04792(16) 0.48114(11) 0.0262(4) Uani 1 1 d . . . . .
N23 N 0.34784(10) 0.45293(17) 0.32807(11) 0.0294(4) Uani 1 1 d . . . . .
H23 H 0.3662 0.3784 0.3117 0.035 Uiso 1 1 calc R . . . .
C1 C 0.01604(12) 1.2442(2) 0.39994(15) 0.0343(6) Uani 1 1 d . . . . .
H1 H -0.0264 1.2920 0.3832 0.041 Uiso 1 1 calc R . . . .
C2 C 0.07750(12) 1.2657(2) 0.47253(14) 0.0306(5) Uani 1 1 d . . . . .
H2 H 0.0776 1.3274 0.5060 0.037 Uiso 1 1 calc R . . . .
C3 C 0.13938(11) 1.1948(2) 0.49571(13) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.21183(12) 1.1961(2) 0.56449(13) 0.0260(5) Uani 1 1 d . . . . .
C5 C 0.24455(12) 1.2646(2) 0.63340(13) 0.0311(5) Uani 1 1 d . . . . .
H5 H 0.2177 1.3257 0.6416 0.037 Uiso 1 1 calc R . . . .
C6 C 0.31635(13) 1.2423(2) 0.68939(14) 0.0335(5) Uani 1 1 d . . . . .
H6 H 0.3392 1.2891 0.7362 0.040 Uiso 1 1 calc R . . . .
C7 C 0.35588(12) 1.1521(2) 0.67848(14) 0.0324(5) Uani 1 1 d . . . . .
H7 H 0.4053 1.1385 0.7181 0.039 Uiso 1 1 calc R . . . .
C8 C 0.32473(12) 1.0817(2) 0.61109(13) 0.0294(5) Uani 1 1 d . . . . .
H8 H 0.3517 1.0195 0.6042 0.035 Uiso 1 1 calc R . . . .
C9 C 0.25237(11) 1.1055(2) 0.55379(13) 0.0261(5) Uani 1 1 d . . . . .
C11 C 0.13804(11) 1.1032(2) 0.44593(13) 0.0257(5) Uani 1 1 d . . . . .
C12 C 0.07615(12) 1.0819(2) 0.37279(14) 0.0308(5) Uani 1 1 d . . . . .
H12 H 0.0755 1.0202 0.3390 0.037 Uiso 1 1 calc R . . . .
C13 C 0.01560(12) 1.1534(2) 0.35100(14) 0.0338(6) Uani 1 1 d . . . . .
H13 H -0.0274 1.1403 0.3014 0.041 Uiso 1 1 calc R . . . .
C14 C 0.22777(11) 0.9512(2) 0.44982(13) 0.0258(5) Uani 1 1 d . . . . .
C15 C 0.29716(12) 0.9489(2) 0.45497(13) 0.0281(5) Uani 1 1 d . . . . .
H15 H 0.3290 1.0145 0.4760 0.034 Uiso 1 1 calc R . . . .
C16 C 0.32002(12) 0.8513(2) 0.42962(13) 0.0279(5) Uani 1 1 d . . . . .
H16 H 0.3683 0.8492 0.4357 0.033 Uiso 1 1 calc R . . . .
C17 C 0.27311(11) 0.7562(2) 0.39535(12) 0.0257(5) Uani 1 1 d . . . . .
C18 C 0.20233(12) 0.7614(2) 0.38741(13) 0.0278(5) Uani 1 1 d . . . . .
H18 H 0.1690 0.6986 0.3623 0.033 Uiso 1 1 calc R . . . .
C19 C 0.18021(12) 0.8565(2) 0.41558(13) 0.0275(5) Uani 1 1 d . . . . .
H19 H 0.1327 0.8573 0.4117 0.033 Uiso 1 1 calc R . . . .
C20 C 0.29885(11) 0.65035(19) 0.37129(13) 0.0251(5) Uani 1 1 d . . . . .
C21 C 0.37121(12) 0.6108(2) 0.41688(13) 0.0290(5) Uani 1 1 d . . . . .
H21 H 0.4044 0.6522 0.4635 0.035 Uiso 1 1 calc R . . . .
C22 C 0.39410(12) 0.5117(2) 0.39398(14) 0.0313(5) Uani 1 1 d . . . . .
H22 H 0.4432 0.4847 0.4252 0.038 Uiso 1 1 calc R . . . .
C24 C 0.27790(12) 0.4889(2) 0.28275(13) 0.0291(5) Uani 1 1 d . . . . .
H24 H 0.2461 0.4461 0.2361 0.035 Uiso 1 1 calc R . . . .
C25 C 0.25204(12) 0.5863(2) 0.30303(13) 0.0268(5) Uani 1 1 d . . . . .
H25 H 0.2025 0.6105 0.2709 0.032 Uiso 1 1 calc R . . . .
C76 C 0.45873(12) 0.2291(2) 0.36000(14) 0.0343(5) Uani 1 1 d . U . . .
C77 C 0.47915(15) 0.0986(3) 0.3673(2) 0.0576(8) Uani 1 1 d . 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
F73A C77 1.278(10) . ?
F73B C77 1.320(7) . ?
F74A C77 1.515(6) . ?
F74B C77 1.243(5) . ?
F75A C77 1.259(5) . ?
F75B C77 1.435(5) . ?
O71 C76 1.253(3) . ?
O72 C76 1.223(3) . ?
N10 C9 1.410(3) . ?
N10 C11 1.404(3) . ?
N10 C14 1.416(3) . ?
N23 H23 1.0400 . ?
N23 C22 1.340(3) . ?
N23 C24 1.346(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(3) . ?
C1 C13 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 C4 1.445(3) . ?
C3 C11 1.404(3) . ?
C4 C5 1.395(3) . ?
C4 C9 1.408(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(3) . ?
C11 C12 1.392(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 C19 1.397(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C17 C18 1.400(3) . ?
C17 C20 1.480(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(3) . ?
C20 C25 1.400(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(3) . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.368(3) . ?
C25 H25 0.9500 . ?
C76 C77 1.536(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C14 125.79(18) . . ?
C11 N10 C9 107.84(18) . . ?
C11 N10 C14 126.36(18) . . ?
C22 N23 H23 119.5 . . ?
C22 N23 C24 121.0(2) . . ?
C24 N23 H23 119.5 . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C13 120.8(2) . . ?
C13 C1 H1 119.6 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 132.7(2) . . ?
C2 C3 C11 120.0(2) . . ?
C11 C3 C4 107.36(19) . . ?
C5 C4 C3 133.4(2) . . ?
C5 C4 C9 119.7(2) . . ?
C9 C4 C3 106.97(19) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.5(2) . . ?
C9 C8 H8 121.2 . . ?
C4 C9 N10 108.85(18) . . ?
C8 C9 N10 129.7(2) . . ?
C8 C9 C4 121.4(2) . . ?
C3 C11 N10 108.97(18) . . ?
C12 C11 N10 129.7(2) . . ?
C12 C11 C3 121.3(2) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.7(2) . . ?
C13 C12 H12 121.2 . . ?
C1 C13 H13 119.2 . . ?
C12 C13 C1 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C15 C14 N10 119.7(2) . . ?
C15 C14 C19 119.4(2) . . ?
C19 C14 N10 120.88(19) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 118.4(2) . . ?
C16 C17 C20 120.56(19) . . ?
C18 C17 C20 121.0(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(2) . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C17 120.5(2) . . ?
C21 C20 C25 117.9(2) . . ?
C25 C20 C17 121.55(19) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
N23 C22 C21 120.6(2) . . ?
N23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
N23 C24 H24 119.6 . . ?
N23 C24 C25 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
O71 C76 C77 112.9(2) . . ?
O72 C76 O71 129.7(3) . . ?
O72 C76 C77 117.3(2) . . ?
F73A C77 F74A 102.7(5) . . ?
F73A C77 C76 111.1(7) . . ?
F73B C77 F75B 99.0(5) . . ?
F73B C77 C76 117.1(5) . . ?
F74A C77 C76 98.8(3) . . ?
F74B C77 F73B 103.8(5) . . ?
F74B C77 F75B 103.2(4) . . ?
F74B C77 C76 120.1(4) . . ?
F75A C77 F73A 129.3(8) . . ?
F75A C77 F74A 95.0(5) . . ?
F75A C77 C76 112.5(3) . . ?
F75B C77 C76 110.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L4Hc
_database_code_depnum_ccdc_archive 'CCDC 2080292'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L4Hc                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2, C6 H5 O3 S'
_chemical_formula_sum            'C29 H22 N2 O3 S'
_chemical_formula_weight         478.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H22 N2 O3 S'
_chemical_oxdiff_usercomment     MeOH
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.2538(3)
_cell_length_b                   10.06550(10)
_cell_length_c                   12.6514(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.699(2)
_cell_angle_gamma                90
_cell_volume                     2267.63(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6605
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.2740
_cell_measurement_theta_min      2.4480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.561
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 6 1 0.0263
2 -6 0 0.0383
1 -3 -7 0.1080
0 -3 7 0.0813
12 1 0 0.0116
-12 -1 0 0.0116

_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.023
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 6.0000 1.0000 -0.8271 -0.0923 0.4318
2.0001 -6.0000 -0.0000 0.8735 0.1001 -0.3161
0.9999 -3.0000 -7.0000 0.1119 -0.0045 -0.9676
0.0002 -3.0000 7.0000 0.7505 0.0194 0.6412
12.0000 1.0000 -0.0000 -0.0087 1.0336 0.1802
-12.0000 -1.0000 0.0000 0.0087 -1.0336 -0.1802

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.122
_diffrn_reflns_theta_min         2.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  31.00   1.00    7.50    --  -41.65  57.00-120.00  100
  2  ω    -94.00 -51.00   1.00    7.50    --  -41.65 125.00 -60.00   43
  3  ω    -65.00  33.00   1.00    7.50    --  -41.65  37.00  30.00   98
  4  ω   -109.00 -20.00   1.00    7.50    --  -41.65 -57.00  90.00   89
  5  ω     29.00 108.00   1.00   30.00    --  112.00 -94.00-120.00   79
  6  ω    137.00 178.00   1.00   30.00    --  112.00 111.00 -90.00   41
  7  ω    101.00 177.00   1.00   30.00    --  112.00 120.00 -55.00   76
  8  ω     37.00 116.00   1.00   30.00    --  112.00-111.00 150.00   79
  9  ω     42.00 140.00   1.00   30.00    --  112.00 -30.00 -30.00   98
 10  ω     39.00 137.00   1.00   30.00    --  112.00 -45.00-150.00   98
 11  ω     85.00 178.00   1.00   30.00    --  112.00  30.00  30.00   93
 12  ω     71.00 116.00   1.00   30.00    --  112.00-111.00 -30.00   45
 13  ω     89.00 178.00   1.00   30.00    --  112.00  30.00 -60.00   89
 14  ω     47.00 143.00   1.00   30.00    --  112.00 -77.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0110967000
_diffrn_orient_matrix_UB_12      -0.1418847000
_diffrn_orient_matrix_UB_13      0.0464129000
_diffrn_orient_matrix_UB_21      0.0851558000
_diffrn_orient_matrix_UB_22      0.0117103000
_diffrn_orient_matrix_UB_23      0.0077872000
_diffrn_orient_matrix_UB_31      0.0103367000
_diffrn_orient_matrix_UB_32      0.0561320000
_diffrn_orient_matrix_UB_33      0.1156548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3753
_reflns_number_total             4474
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.7918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N23(H23), C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25),
  C76(H76), C77(H77), C78(H78), C79(H79), C80(H80)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S74 S 0.41442(2) 0.78108(4) 0.80315(3) 0.01890(11) Uani 1 1 d . . . . .
O71 O 0.46584(7) 0.87940(11) 0.77317(9) 0.0234(2) Uani 1 1 d . . . . .
O72 O 0.43662(7) 0.64699(11) 0.78110(10) 0.0284(3) Uani 1 1 d . . . . .
O73 O 0.40199(7) 0.80190(14) 0.91104(10) 0.0298(3) Uani 1 1 d . . . . .
N10 N 0.81931(8) 0.65267(13) 0.18739(11) 0.0203(3) Uani 1 1 d . . . . .
N23 N 0.53921(8) 0.78081(14) 0.62634(11) 0.0227(3) Uani 1 1 d . . . . .
H23 H 0.5098 0.7990 0.6865 0.027 Uiso 1 1 calc R . . . .
C1 C 0.98613(10) 0.37407(18) 0.18249(13) 0.0254(3) Uani 1 1 d . . . . .
H1 H 1.0250 0.3150 0.1807 0.030 Uiso 1 1 calc R . . . .
C2 C 0.98470(9) 0.49670(18) 0.13229(13) 0.0239(3) Uani 1 1 d . . . . .
H2 H 1.0223 0.5205 0.0969 0.029 Uiso 1 1 calc R . . . .
C3 C 0.92570(9) 0.58397(16) 0.13570(12) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.90750(9) 0.71664(16) 0.09357(12) 0.0208(3) Uani 1 1 d . . . . .
C5 C 0.94037(10) 0.80266(18) 0.03099(13) 0.0249(3) Uani 1 1 d . . . . .
H5 H 0.9832 0.7775 0.0077 0.030 Uiso 1 1 calc R . . . .
C6 C 0.90817(10) 0.92598(18) 0.00420(14) 0.0286(4) Uani 1 1 d . . . . .
H6 H 0.9297 0.9843 -0.0372 0.034 Uiso 1 1 calc R . . . .
C7 C 0.84355(10) 0.96369(17) 0.03875(14) 0.0277(4) Uani 1 1 d . . . . .
H7 H 0.8226 1.0468 0.0194 0.033 Uiso 1 1 calc R . . . .
C8 C 0.80988(10) 0.88012(17) 0.10120(13) 0.0238(3) Uani 1 1 d . . . . .
H8 H 0.7669 0.9057 0.1241 0.029 Uiso 1 1 calc R . . . .
C9 C 0.84286(9) 0.75610(16) 0.12839(12) 0.0203(3) Uani 1 1 d . . . . .
C11 C 0.87009(9) 0.54751(15) 0.19178(12) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.87105(9) 0.42382(16) 0.24212(13) 0.0217(3) Uani 1 1 d . . . . .
H12 H 0.8340 0.3996 0.2784 0.026 Uiso 1 1 calc R . . . .
C13 C 0.92975(10) 0.33851(17) 0.23567(13) 0.0248(3) Uani 1 1 d . . . . .
H13 H 0.9315 0.2551 0.2678 0.030 Uiso 1 1 calc R . . . .
C14 C 0.76830(9) 0.66939(16) 0.25672(12) 0.0191(3) Uani 1 1 d . . . . .
C15 C 0.77380(9) 0.78380(16) 0.32032(13) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.8110 0.8462 0.3179 0.026 Uiso 1 1 calc R . . . .
C16 C 0.72438(9) 0.80467(15) 0.38667(13) 0.0206(3) Uani 1 1 d . . . . .
H16 H 0.7276 0.8826 0.4270 0.025 Uiso 1 1 calc R . . . .
C17 C 0.66955(9) 0.71062(15) 0.39436(12) 0.0188(3) Uani 1 1 d . . . . .
C18 C 0.66544(9) 0.59427(15) 0.33255(13) 0.0194(3) Uani 1 1 d . . . . .
H18 H 0.6301 0.5296 0.3382 0.023 Uiso 1 1 calc R . . . .
C19 C 0.71365(9) 0.57465(15) 0.26298(13) 0.0201(3) Uani 1 1 d . . . . .
H19 H 0.7095 0.4984 0.2206 0.024 Uiso 1 1 calc R . . . .
C20 C 0.62045(9) 0.73314(15) 0.47122(12) 0.0190(3) Uani 1 1 d . . . . .
C21 C 0.60001(9) 0.86268(16) 0.49432(13) 0.0213(3) Uani 1 1 d . . . . .
H21 H 0.6134 0.9343 0.4561 0.026 Uiso 1 1 calc R . . . .
C22 C 0.56036(9) 0.88373(17) 0.57314(13) 0.0229(3) Uani 1 1 d . . . . .
H22 H 0.5481 0.9698 0.5897 0.028 Uiso 1 1 calc R . . . .
C24 C 0.55486(9) 0.65438(17) 0.60434(13) 0.0234(3) Uani 1 1 d . . . . .
H24 H 0.5381 0.5847 0.6411 0.028 Uiso 1 1 calc R . . . .
C25 C 0.59556(9) 0.62858(16) 0.52759(13) 0.0215(3) Uani 1 1 d . . . . .
H25 H 0.6067 0.5413 0.5129 0.026 Uiso 1 1 calc R . . . .
C75 C 0.32681(9) 0.81046(15) 0.71153(13) 0.0202(3) Uani 1 1 d . . . . .
C76 C 0.26565(10) 0.85516(15) 0.74940(14) 0.0235(3) Uani 1 1 d . . . . .
H76 H 0.2697 0.8688 0.8232 0.028 Uiso 1 1 calc R . . . .
C77 C 0.19793(10) 0.87963(17) 0.67646(16) 0.0281(4) Uani 1 1 d . . . . .
H77 H 0.1567 0.9096 0.7016 0.034 Uiso 1 1 calc R . . . .
C78 C 0.19182(10) 0.85943(17) 0.56652(16) 0.0308(4) Uani 1 1 d . . . . .
H78 H 0.1464 0.8749 0.5179 0.037 Uiso 1 1 calc R . . . .
C79 C 0.25378(11) 0.81600(18) 0.52924(14) 0.0302(4) Uani 1 1 d . . . . .
H79 H 0.2498 0.8038 0.4553 0.036 Uiso 1 1 calc R . . . .
C80 C 0.32144(10) 0.79067(16) 0.60097(14) 0.0248(3) Uani 1 1 d . . . . .
H80 H 0.3627 0.7609 0.5757 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S74 O71 1.4699(12) . ?
S74 O72 1.4538(12) . ?
S74 O73 1.4473(12) . ?
S74 C75 1.7813(17) . ?
N10 C9 1.402(2) . ?
N10 C11 1.400(2) . ?
N10 C14 1.423(2) . ?
N23 H23 1.0400 . ?
N23 C22 1.338(2) . ?
N23 C24 1.347(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(3) . ?
C1 C13 1.394(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(2) . ?
C3 C4 1.449(2) . ?
C3 C11 1.409(2) . ?
C4 C5 1.395(2) . ?
C4 C9 1.404(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.398(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(2) . ?
C11 C12 1.397(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(2) . ?
C14 C19 1.395(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.397(2) . ?
C17 C18 1.401(2) . ?
C17 C20 1.478(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.405(2) . ?
C20 C25 1.402(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(2) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.371(2) . ?
C25 H25 0.9300 . ?
C75 C76 1.383(2) . ?
C75 C80 1.395(2) . ?
C76 H76 0.9300 . ?
C76 C77 1.392(3) . ?
C77 H77 0.9300 . ?
C77 C78 1.386(3) . ?
C78 H78 0.9300 . ?
C78 C79 1.388(3) . ?
C79 H79 0.9300 . ?
C79 C80 1.386(3) . ?
C80 H80 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O71 S74 C75 104.66(7) . . ?
O72 S74 O71 110.78(7) . . ?
O72 S74 C75 106.11(7) . . ?
O73 S74 O71 112.79(7) . . ?
O73 S74 O72 115.05(8) . . ?
O73 S74 C75 106.58(8) . . ?
C9 N10 C14 123.99(13) . . ?
C11 N10 C9 107.74(13) . . ?
C11 N10 C14 125.62(13) . . ?
C22 N23 H23 119.0 . . ?
C22 N23 C24 122.01(14) . . ?
C24 N23 H23 119.0 . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C13 120.55(15) . . ?
C13 C1 H1 119.7 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.86(15) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 133.13(15) . . ?
C2 C3 C11 119.82(15) . . ?
C11 C3 C4 107.03(14) . . ?
C5 C4 C3 133.50(16) . . ?
C5 C4 C9 119.89(15) . . ?
C9 C4 C3 106.60(14) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.91(16) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.63(16) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.58(16) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.51(16) . . ?
C9 C8 H8 121.2 . . ?
N10 C9 C4 109.50(14) . . ?
C8 C9 N10 128.98(15) . . ?
C8 C9 C4 121.48(15) . . ?
N10 C11 C3 109.09(14) . . ?
C12 C11 N10 129.34(14) . . ?
C12 C11 C3 121.57(15) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.17(15) . . ?
C13 C12 H12 121.4 . . ?
C1 C13 H13 119.0 . . ?
C12 C13 C1 122.02(16) . . ?
C12 C13 H13 119.0 . . ?
C15 C14 N10 118.63(14) . . ?
C19 C14 N10 121.83(14) . . ?
C19 C14 C15 119.54(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.24(15) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.98(15) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 118.62(14) . . ?
C16 C17 C20 119.31(14) . . ?
C18 C17 C20 121.99(14) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.60(14) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 119.97(14) . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C17 120.44(14) . . ?
C25 C20 C17 122.07(14) . . ?
C25 C20 C21 117.42(15) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.10(15) . . ?
C22 C21 H21 120.0 . . ?
N23 C22 C21 120.20(15) . . ?
N23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
N23 C24 H24 120.1 . . ?
N23 C24 C25 119.87(15) . . ?
C25 C24 H24 120.1 . . ?
C20 C25 H25 119.8 . . ?
C24 C25 C20 120.32(15) . . ?
C24 C25 H25 119.8 . . ?
C76 C75 S74 120.40(13) . . ?
C76 C75 C80 120.64(16) . . ?
C80 C75 S74 118.95(13) . . ?
C75 C76 H76 120.2 . . ?
C75 C76 C77 119.64(16) . . ?
C77 C76 H76 120.2 . . ?
C76 C77 H77 119.9 . . ?
C78 C77 C76 120.20(17) . . ?
C78 C77 H77 119.9 . . ?
C77 C78 H78 120.2 . . ?
C77 C78 C79 119.70(16) . . ?
C79 C78 H78 120.2 . . ?
C78 C79 H79 119.6 . . ?
C80 C79 C78 120.71(16) . . ?
C80 C79 H79 119.6 . . ?
C75 C80 H80 120.4 . . ?
C79 C80 C75 119.10(16) . . ?
C79 C80 H80 120.4 . . ?


_ins_header                      
;
TITL OHI-082_scale in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  18.253752  10.065530  12.651444  90.0000 102.6988  90.0000
ZERR    4.00   0.000278   0.000125   0.000168   0.0000   0.0015   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O S
UNIT 116.00 88.00 8.00 12.00 4.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_L1He
_database_code_depnum_ccdc_archive 'CCDC 2080288'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L1He                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 N2 O, C2 H Br2 O2'
_chemical_formula_sum            'C32 H22 Br2 N2 O3'
_chemical_formula_weight         642.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8699(3)
_cell_length_b                   11.5839(5)
_cell_length_c                   13.0739(6)
_cell_angle_alpha                76.151(4)
_cell_angle_beta                 77.907(3)
_cell_angle_gamma                66.362(4)
_cell_volume                     1318.67(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5942
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.3540
_cell_measurement_theta_min      3.4760
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             644
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 5 1 0.0491
-6 -5 -1 0.0491
1 -6 2 0.0396
-1 6 -2 0.0396
2 1 8 0.0326
-1 -1 -8 0.0463
2 -2 -7 0.0529
0 5 7 0.0411
0 -5 -7 0.0411

_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9791
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.121
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -28.00   1.00    1.00    --  -41.78 -37.00  90.00   88
  2  ω   -110.00 -10.00   1.00    1.00    --  -41.78 -77.00-150.00  100
  3  ω      1.00  43.00   1.00    1.00    --   41.78 -99.00 -30.00   42
  4  ω     76.00 116.00   1.00    1.00    --   41.78  37.00  60.00   40
  5  ω     23.00  98.00   1.00    1.00    --   41.78-125.00  60.00   75
  6  ω     21.00  48.00   1.00    1.00    --   41.78  37.00  60.00   27
  7  ω     43.00 116.00   1.00    3.00    --  112.00-111.00 -30.00   73
  8  ω     84.00 168.00   1.00    3.00    --  112.00  61.00  60.00   84
  9  ω     38.00 137.00   1.00    3.00    --  112.00 -30.00 120.00   99
 10  ω    103.00 178.00   1.00    3.00    --  112.00  61.00  90.00   75
 11  ω     85.00 176.00   1.00    3.00    --  112.00  61.00 150.00   91
 12  ω     70.00 109.00   1.00    3.00    --  112.00 -94.00  90.00   39
 13  ω     95.00 122.00   1.00    3.00    --  112.00  30.00   0.00   27
 14  ω    103.00 131.00   1.00    3.00    --  112.00 111.00   0.00   28
 15  ω     55.00 115.00   1.00    3.00    --  112.00-111.00-150.00   60
 16  ω    144.00 174.00   1.00    3.00    --  112.00 111.00   0.00   30
 17  ω     45.00 103.00   1.00    3.00    --  112.00-111.00 -60.00   58
 18  ω    149.00 178.00   1.00    3.00    --  112.00  30.00   0.00   29
 19  ω     35.00  75.00   1.00    3.00    --  112.00 -94.00   0.00   40
 20  ω     81.00 107.00   1.00    3.00    --  112.00 -94.00   0.00   26
 21  ω     43.00 138.00   1.00    3.00    --  112.00 -61.00   0.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4558
_reflns_number_total             5164
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.891
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+0.8495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0799
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C54(H54)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br55 Br 0.38170(3) 0.07512(2) 1.24287(2) 0.03357(9) Uani 1 1 d . . . . .
Br56 Br 0.22442(3) 0.32270(3) 1.35453(2) 0.03074(8) Uani 1 1 d . . . . .
O51 O 0.18986(19) 0.42438(17) 1.08905(14) 0.0293(4) Uani 1 1 d . . . . .
O52 O 0.4310(2) 0.3185(2) 1.10660(15) 0.0366(4) Uani 1 1 d . . . . .
C53 C 0.2984(3) 0.3377(2) 1.13195(18) 0.0221(4) Uani 1 1 d . . . . .
C54 C 0.2462(2) 0.2508(2) 1.22795(18) 0.0222(4) Uani 1 1 d . . . . .
H54 H 0.1484 0.2545 1.2188 0.027 Uiso 1 1 calc R . . . .
O27 O -0.03896(19) 0.81129(18) -0.10043(14) 0.0304(4) Uani 1 1 d . . . . .
N1 N 0.2607(2) 0.51484(18) 0.89318(15) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.2470 0.4843 0.9749 0.027 Uiso 1 1 calc R . . . .
N11 N 0.3926(2) 0.74500(19) 0.23013(15) 0.0217(4) Uani 1 1 d . . . . .
C2 C 0.1558(3) 0.5296(2) 0.83574(19) 0.0251(5) Uani 1 1 d . . . . .
H2 H 0.0708 0.5134 0.8694 0.030 Uiso 1 1 calc R . . . .
C3 C 0.1720(2) 0.5684(2) 0.72772(19) 0.0245(5) Uani 1 1 d . . . . .
H3 H 0.0977 0.5783 0.6892 0.029 Uiso 1 1 calc R . . . .
C4 C 0.2986(2) 0.5933(2) 0.67473(17) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.4047(3) 0.5780(2) 0.73847(18) 0.0236(4) Uani 1 1 d . . . . .
H5 H 0.4904 0.5944 0.7072 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3838(3) 0.5391(2) 0.84641(18) 0.0234(4) Uani 1 1 d . . . . .
H6 H 0.4553 0.5294 0.8875 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3182(2) 0.6342(2) 0.55856(17) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.2131(3) 0.6406(2) 0.49651(18) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.1314 0.6195 0.5307 0.031 Uiso 1 1 calc R . . . .
C9 C 0.2264(3) 0.6769(3) 0.38758(19) 0.0271(5) Uani 1 1 d . . . . .
H9 H 0.1549 0.6810 0.3490 0.033 Uiso 1 1 calc R . . . .
C10 C 0.3504(2) 0.7071(2) 0.33687(18) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.5294(2) 0.7603(2) 0.21988(18) 0.0202(4) Uani 1 1 d . . . . .
C13 C 0.6213(3) 0.7855(2) 0.12803(18) 0.0232(4) Uani 1 1 d . . . . .
H13 H 0.5940 0.7994 0.0610 0.028 Uiso 1 1 calc R . . . .
C14 C 0.7557(3) 0.7892(2) 0.14086(19) 0.0255(5) Uani 1 1 d . . . . .
H14 H 0.8203 0.8045 0.0810 0.031 Uiso 1 1 calc R . . . .
C15 C 0.7964(3) 0.7706(3) 0.2416(2) 0.0288(5) Uani 1 1 d . . . . .
H15 H 0.8856 0.7765 0.2475 0.035 Uiso 1 1 calc R . . . .
C16 C 0.7055(3) 0.7436(2) 0.33257(19) 0.0254(5) Uani 1 1 d . . . . .
H16 H 0.7329 0.7311 0.3994 0.030 Uiso 1 1 calc R . . . .
C17 C 0.5717(2) 0.7356(2) 0.32186(17) 0.0209(4) Uani 1 1 d . . . . .
C18 C 0.4576(2) 0.7017(2) 0.39680(18) 0.0201(4) Uani 1 1 d . . . . .
C19 C 0.4408(2) 0.6656(2) 0.50651(17) 0.0200(4) Uani 1 1 d . . . . .
H19 H 0.5115 0.6623 0.5455 0.024 Uiso 1 1 calc R . . . .
C20 C 0.3086(2) 0.7718(2) 0.14554(17) 0.0210(4) Uani 1 1 d . . . . .
C21 C 0.2401(2) 0.6900(2) 0.13858(18) 0.0229(4) Uani 1 1 d . . . . .
H21 H 0.2500 0.6165 0.1892 0.028 Uiso 1 1 calc R . . . .
C22 C 0.1579(2) 0.7182(2) 0.05665(18) 0.0226(4) Uani 1 1 d . . . . .
H22 H 0.1068 0.6666 0.0550 0.027 Uiso 1 1 calc R . . . .
C23 C 0.1505(2) 0.8235(2) -0.02403(18) 0.0219(4) Uani 1 1 d . . . . .
C24 C 0.2198(3) 0.9050(2) -0.01731(18) 0.0231(4) Uani 1 1 d . . . . .
H24 H 0.2149 0.9757 -0.0704 0.028 Uiso 1 1 calc R . . . .
C25 C 0.2958(3) 0.8811(2) 0.06813(18) 0.0230(4) Uani 1 1 d . . . . .
H25 H 0.3381 0.9376 0.0739 0.028 Uiso 1 1 calc R . . . .
C26 C 0.0666(2) 0.8463(2) -0.11442(18) 0.0228(4) Uani 1 1 d . . . . .
C28 C 0.1138(3) 0.9084(2) -0.22195(18) 0.0226(4) Uani 1 1 d . . . . .
C29 C 0.0056(3) 0.9782(2) -0.2902(2) 0.0292(5) Uani 1 1 d . . . . .
H29 H -0.0939 0.9898 -0.2666 0.035 Uiso 1 1 calc R . . . .
C30 C 0.0470(3) 1.0298(3) -0.3931(2) 0.0362(6) Uani 1 1 d . . . . .
H30 H -0.0254 1.0782 -0.4379 0.043 Uiso 1 1 calc R . . . .
C31 C 0.1957(3) 1.0099(3) -0.4299(2) 0.0360(6) Uani 1 1 d . . . . .
H31 H 0.2231 1.0430 -0.4997 0.043 Uiso 1 1 calc R . . . .
C32 C 0.3038(3) 0.9404(3) -0.3624(2) 0.0323(5) Uani 1 1 d . . . . .
H32 H 0.4035 0.9268 -0.3872 0.039 Uiso 1 1 calc R . . . .
C33 C 0.2633(3) 0.8910(2) -0.25808(19) 0.0248(5) Uani 1 1 d . . . . .
H33 H 0.3353 0.8466 -0.2124 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br55 C54 1.925(2) . ?
Br56 C54 1.961(2) . ?
O51 C53 1.261(3) . ?
O52 C53 1.222(3) . ?
C53 C54 1.547(3) . ?
C54 H54 0.9800 . ?
O27 C26 1.227(3) . ?
N1 H1 1.0400 . ?
N1 C2 1.337(3) . ?
N1 C6 1.345(3) . ?
N11 C10 1.387(3) . ?
N11 C12 1.406(3) . ?
N11 C20 1.422(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.403(3) . ?
C4 C7 1.475(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(3) . ?
C7 C19 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(3) . ?
C10 C18 1.418(3) . ?
C12 C13 1.392(3) . ?
C12 C17 1.410(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.399(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.398(3) . ?
C17 C18 1.445(3) . ?
C18 C19 1.389(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(3) . ?
C20 C25 1.399(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.397(3) . ?
C23 C24 1.396(3) . ?
C23 C26 1.496(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(3) . ?
C25 H25 0.9300 . ?
C26 C28 1.491(3) . ?
C28 C29 1.397(3) . ?
C28 C33 1.398(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.384(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.388(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.389(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.389(3) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O51 C53 C54 111.75(19) . . ?
O52 C53 O51 127.9(2) . . ?
O52 C53 C54 120.4(2) . . ?
Br55 C54 Br56 110.97(11) . . ?
Br55 C54 H54 108.7 . . ?
Br56 C54 H54 108.7 . . ?
C53 C54 Br55 112.87(15) . . ?
C53 C54 Br56 106.89(15) . . ?
C53 C54 H54 108.7 . . ?
C2 N1 H1 119.6 . . ?
C2 N1 C6 120.7(2) . . ?
C6 N1 H1 119.6 . . ?
C10 N11 C12 108.38(18) . . ?
C10 N11 C20 126.24(19) . . ?
C12 N11 C20 125.27(19) . . ?
N1 C2 H2 119.6 . . ?
N1 C2 C3 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 116.2(2) . . ?
C3 C4 C7 121.6(2) . . ?
C5 C4 C7 122.2(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 120.4(2) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C4 120.4(2) . . ?
C19 C7 C4 121.5(2) . . ?
C19 C7 C8 118.2(2) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.1(2) . . ?
C10 C9 H9 121.0 . . ?
N11 C10 C9 130.6(2) . . ?
N11 C10 C18 109.06(19) . . ?
C9 C10 C18 120.4(2) . . ?
N11 C12 C17 108.83(19) . . ?
C13 C12 N11 129.1(2) . . ?
C13 C12 C17 121.9(2) . . ?
C12 C13 H13 121.4 . . ?
C14 C13 C12 117.2(2) . . ?
C14 C13 H13 121.4 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.7(2) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.7 . . ?
C15 C16 C17 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C12 C17 C18 106.9(2) . . ?
C16 C17 C12 119.7(2) . . ?
C16 C17 C18 133.4(2) . . ?
C10 C18 C17 106.83(19) . . ?
C19 C18 C10 120.3(2) . . ?
C19 C18 C17 132.9(2) . . ?
C7 C19 H19 119.9 . . ?
C18 C19 C7 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C21 C20 N11 120.8(2) . . ?
C21 C20 C25 119.9(2) . . ?
C25 C20 N11 119.3(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(2) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.2(2) . . ?
C22 C23 C26 118.8(2) . . ?
C24 C23 C26 122.1(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
O27 C26 C23 120.0(2) . . ?
O27 C26 C28 120.2(2) . . ?
C28 C26 C23 119.9(2) . . ?
C29 C28 C26 118.1(2) . . ?
C29 C28 C33 119.8(2) . . ?
C33 C28 C26 121.9(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.5(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 119.9(2) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.2(3) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.8(2) . . ?
C32 C33 H33 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L1Hb
_database_code_depnum_ccdc_archive 'CCDC 2080286'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-04-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L1Hb                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        BpCzdPy/TCA
_chemical_formula_moiety         'C30 H21 N2 O, C2 Cl3 O2'
_chemical_formula_sum            'C32 H21 Cl3 N2 O3'
_chemical_formula_weight         587.86
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3051(4)
_cell_length_b                   11.6453(4)
_cell_length_c                   12.1129(5)
_cell_angle_alpha                64.6230(10)
_cell_angle_beta                 73.099(2)
_cell_angle_gamma                87.411(2)
_cell_volume                     1372.74(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3760
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      28.700
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.8197.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7013
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.944
_diffrn_reflns_theta_min         1.944
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4031
_reflns_number_total             7013
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2015)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         7013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.0765
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1053P)²+0.4675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.2262
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.746(3)
 0.254(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3. Others
 Sof(Cl62)=Sof(Cl63)=Sof(Cl64)=Sof(O58)=Sof(O59)=Sof(C60)=Sof(C61)=1-FVAR(1)
 Sof(Cl55)=Sof(Cl56)=Sof(Cl57)=Sof(O51)=Sof(O52)=Sof(C53)=Sof(C54)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O27 O 0.6448(3) 0.8727(3) -0.3879(2) 0.0798(9) Uani 1 1 d . . . . .
N1 N 0.4313(3) 0.0198(2) 0.8281(3) 0.0487(6) Uani 1 1 d . . . . .
H1 H 0.3935 -0.0609 0.9134 0.058 Uiso 1 1 calc R . . . .
N11 N 0.7495(2) 0.6786(2) 0.1486(2) 0.0447(6) Uani 1 1 d . . . . .
C2 C 0.4122(4) 0.0312(3) 0.7207(3) 0.0589(9) Uani 1 1 d . . . . .
H2 H 0.3640 -0.0349 0.7229 0.071 Uiso 1 1 calc R . . . .
C3 C 0.4609(3) 0.1364(3) 0.6072(3) 0.0513(8) Uani 1 1 d . . . . .
H3 H 0.4461 0.1420 0.5319 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5317(3) 0.2355(3) 0.6002(3) 0.0382(6) Uani 1 1 d . . . . .
C5 C 0.5500(3) 0.2183(3) 0.7152(3) 0.0521(8) Uani 1 1 d . . . . .
H5 H 0.5990 0.2819 0.7161 0.062 Uiso 1 1 calc R . . . .
C6 C 0.4988(3) 0.1120(3) 0.8265(3) 0.0536(8) Uani 1 1 d . . . . .
H6 H 0.5115 0.1035 0.9037 0.064 Uiso 1 1 calc R . . . .
C7 C 0.5851(3) 0.3500(3) 0.4791(3) 0.0378(6) Uani 1 1 d . . . . .
C8 C 0.5735(3) 0.3608(3) 0.3623(3) 0.0452(7) Uani 1 1 d . . . . .
H8 H 0.5290 0.2932 0.3629 0.054 Uiso 1 1 calc R . . . .
C9 C 0.6237(3) 0.4647(3) 0.2483(3) 0.0465(7) Uani 1 1 d . . . . .
H9 H 0.6146 0.4697 0.1709 0.056 Uiso 1 1 calc R . . . .
C10 C 0.6890(3) 0.5634(3) 0.2490(3) 0.0405(6) Uani 1 1 d . . . . .
C12 C 0.8008(3) 0.7453(3) 0.1997(3) 0.0429(7) Uani 1 1 d . . . . .
C13 C 0.8619(3) 0.8662(3) 0.1400(3) 0.0528(8) Uani 1 1 d . . . . .
H13 H 0.8779 0.9174 0.0506 0.063 Uiso 1 1 calc R . . . .
C14 C 0.8989(3) 0.9095(4) 0.2164(4) 0.0604(9) Uani 1 1 d . . . . .
H14 H 0.9401 0.9928 0.1781 0.072 Uiso 1 1 calc R . . . .
C15 C 0.8780(3) 0.8358(3) 0.3454(3) 0.0538(8) Uani 1 1 d . . . . .
H15 H 0.9072 0.8681 0.3936 0.065 Uiso 1 1 calc R . . . .
C16 C 0.8152(3) 0.7152(3) 0.4062(3) 0.0490(8) Uani 1 1 d . . . . .
H16 H 0.8001 0.6648 0.4956 0.059 Uiso 1 1 calc R . . . .
C17 C 0.7747(3) 0.6698(3) 0.3329(3) 0.0413(7) Uani 1 1 d . . . . .
C18 C 0.7033(3) 0.5549(3) 0.3639(3) 0.0385(6) Uani 1 1 d . . . . .
C19 C 0.6516(3) 0.4488(3) 0.4778(3) 0.0399(6) Uani 1 1 d . . . . .
H19 H 0.6613 0.4430 0.5552 0.048 Uiso 1 1 calc R . . . .
C20 C 0.7456(3) 0.7304(3) 0.0204(3) 0.0420(7) Uani 1 1 d . . . . .
C21 C 0.6334(3) 0.7261(3) -0.0039(3) 0.0444(7) Uani 1 1 d . . . . .
H21 H 0.5605 0.6834 0.0648 0.053 Uiso 1 1 calc R . . . .
C22 C 0.6289(3) 0.7839(3) -0.1278(3) 0.0448(7) Uani 1 1 d . . . . .
H22 H 0.5531 0.7773 -0.1447 0.054 Uiso 1 1 calc R . . . .
C23 C 0.7332(3) 0.8519(3) -0.2288(3) 0.0433(7) Uani 1 1 d . . . . .
C24 C 0.8456(3) 0.8519(3) -0.2044(3) 0.0456(7) Uani 1 1 d . . . . .
H24 H 0.9183 0.8954 -0.2730 0.055 Uiso 1 1 calc R . . . .
C25 C 0.8524(3) 0.7884(3) -0.0801(3) 0.0441(7) Uani 1 1 d . . . . .
H25 H 0.9302 0.7849 -0.0641 0.053 Uiso 1 1 calc R . . . .
C26 C 0.7180(3) 0.9202(3) -0.3591(3) 0.0492(8) Uani 1 1 d . . . . .
C28 C 0.7856(3) 1.0474(3) -0.4514(3) 0.0442(7) Uani 1 1 d . . . . .
C29 C 0.7896(3) 1.0931(4) -0.5796(3) 0.0556(8) Uani 1 1 d . . . . .
H29 H 0.7539 1.0404 -0.6057 0.067 Uiso 1 1 calc R . . . .
C30 C 0.8437(4) 1.2124(4) -0.6684(3) 0.0630(10) Uani 1 1 d . . . . .
H30 H 0.8453 1.2419 -0.7551 0.076 Uiso 1 1 calc R . . . .
C31 C 0.8958(3) 1.2894(4) -0.6318(4) 0.0644(10) Uani 1 1 d . . . . .
H31 H 0.9343 1.3718 -0.6935 0.077 Uiso 1 1 calc R . . . .
C32 C 0.8924(4) 1.2471(3) -0.5053(4) 0.0614(9) Uani 1 1 d . . . . .
H32 H 0.9280 1.3008 -0.4802 0.074 Uiso 1 1 calc R . . . .
C33 C 0.8372(3) 1.1269(3) -0.4153(3) 0.0512(8) Uani 1 1 d . . . . .
H33 H 0.8346 1.0984 -0.3284 0.061 Uiso 1 1 calc R . . . .
Cl55 Cl 0.1361(9) -0.4723(7) 1.0683(7) 0.090(2) Uani 0.495(15) 1 d . . P A 1
Cl56 Cl 0.3194(4) -0.4798(4) 1.1915(7) 0.0846(16) Uani 0.495(15) 1 d . . P A 1
Cl57 Cl 0.1004(9) -0.3548(11) 1.2433(9) 0.107(3) Uani 0.495(15) 1 d . . P A 1
O51 O 0.3342(13) -0.197(2) 1.0389(19) 0.055(5) Uani 0.495(15) 1 d . . P A 1
O52 O 0.2106(14) -0.1990(9) 0.9252(11) 0.100(4) Uani 0.495(15) 1 d . . P A 1
C53 C 0.2515(17) -0.2377(16) 1.008(2) 0.050(3) Uani 0.495(15) 1 d . . P A 1
C54 C 0.218(2) -0.378(2) 1.113(2) 0.046(4) Uani 0.495(15) 1 d . . P A 1
Cl62 Cl 0.3114(5) -0.4868(5) 1.1380(11) 0.1096(18) Uani 0.505(15) 1 d . . P A 2
Cl63 Cl 0.0902(9) -0.4358(8) 1.0689(8) 0.105(2) Uani 0.505(15) 1 d . . P A 2
Cl64 Cl 0.1220(10) -0.3761(10) 1.2575(7) 0.102(3) Uani 0.505(15) 1 d . . P A 2
O58 O 0.3288(18) -0.186(2) 1.041(2) 0.072(6) Uani 0.505(15) 1 d . . P A 2
O59 O 0.2959(13) -0.2444(10) 0.9004(6) 0.094(4) Uani 0.505(15) 1 d . . P A 2
C60 C 0.2863(15) -0.2635(14) 1.0135(19) 0.043(3) Uani 0.505(15) 1 d . . P A 2
C61 C 0.190(2) -0.388(2) 1.125(2) 0.044(4) Uani 0.505(15) 1 d . . 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
O27 C26 1.220(4) . ?
N1 H1 1.0400 . ?
N1 C2 1.330(4) . ?
N1 C6 1.335(4) . ?
N11 C10 1.396(4) . ?
N11 C12 1.408(4) . ?
N11 C20 1.419(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 C5 1.396(4) . ?
C4 C7 1.475(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.366(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.410(4) . ?
C7 C19 1.394(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(4) . ?
C10 C18 1.409(4) . ?
C12 C13 1.380(4) . ?
C12 C17 1.412(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.374(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(4) . ?
C17 C18 1.440(4) . ?
C18 C19 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(4) . ?
C20 C25 1.382(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.390(4) . ?
C23 C24 1.386(4) . ?
C23 C26 1.490(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(4) . ?
C25 H25 0.9500 . ?
C26 C28 1.488(5) . ?
C28 C29 1.396(4) . ?
C28 C33 1.391(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.369(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.374(6) . ?
C31 H31 0.9500 . ?
C31 C32 1.383(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(5) . ?
C33 H33 0.9500 . ?
Cl55 C54 1.81(2) . ?
Cl56 C54 1.78(3) . ?
Cl57 C54 1.85(3) . ?
O51 C53 1.28(2) . ?
O52 C53 1.14(2) . ?
C53 C54 1.55(3) . ?
Cl62 C61 1.75(2) . ?
Cl63 C61 1.70(2) . ?
Cl64 C61 1.62(3) . ?
O58 C60 1.24(3) . ?
O59 C60 1.26(2) . ?
C60 C61 1.65(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 119.9 . . ?
C2 N1 C6 120.1(3) . . ?
C6 N1 H1 119.9 . . ?
C10 N11 C12 108.2(2) . . ?
C10 N11 C20 126.6(2) . . ?
C12 N11 C20 124.5(2) . . ?
N1 C2 H2 119.5 . . ?
N1 C2 C3 121.1(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 115.4(3) . . ?
C3 C4 C7 122.3(3) . . ?
C5 C4 C7 122.3(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 120.8(3) . . ?
N1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C4 121.3(2) . . ?
C19 C7 C4 120.2(2) . . ?
C19 C7 C8 118.6(3) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 H8 118.7 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(3) . . ?
C10 C9 H9 121.0 . . ?
N11 C10 C9 130.4(3) . . ?
N11 C10 C18 108.8(2) . . ?
C9 C10 C18 120.8(3) . . ?
N11 C12 C17 108.6(2) . . ?
C13 C12 N11 129.7(3) . . ?
C13 C12 C17 121.7(3) . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 117.0(3) . . ?
C14 C13 H13 121.5 . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.2(3) . . ?
C17 C16 H16 120.9 . . ?
C12 C17 C18 107.0(2) . . ?
C16 C17 C12 119.8(3) . . ?
C16 C17 C18 133.2(3) . . ?
C10 C18 C17 107.4(2) . . ?
C19 C18 C10 120.0(2) . . ?
C19 C18 C17 132.7(3) . . ?
C7 C19 H19 120.0 . . ?
C18 C19 C7 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C21 C20 N11 119.9(3) . . ?
C25 C20 N11 120.0(3) . . ?
C25 C20 C21 120.1(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.1(3) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C26 117.7(3) . . ?
C24 C23 C22 118.9(3) . . ?
C24 C23 C26 123.4(3) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 119.8(3) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
O27 C26 C23 119.0(3) . . ?
O27 C26 C28 119.7(3) . . ?
C28 C26 C23 121.2(3) . . ?
C29 C28 C26 118.2(3) . . ?
C33 C28 C26 123.4(3) . . ?
C33 C28 C29 118.2(3) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 C28 121.4(3) . . ?
C30 C29 H29 119.3 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.9 . . ?
C30 C31 C32 120.1(3) . . ?
C32 C31 H31 119.9 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.1(3) . . ?
C33 C32 H32 119.9 . . ?
C28 C33 H33 119.9 . . ?
C32 C33 C28 120.3(3) . . ?
C32 C33 H33 119.9 . . ?
O51 C53 C54 102.7(17) . . ?
O52 C53 O51 136(2) . . ?
O52 C53 C54 121.5(17) . . ?
Cl55 C54 Cl57 105.4(12) . . ?
Cl56 C54 Cl55 105.8(13) . . ?
Cl56 C54 Cl57 104.1(12) . . ?
C53 C54 Cl55 111.7(16) . . ?
C53 C54 Cl56 126.6(15) . . ?
C53 C54 Cl57 101.0(16) . . ?
O58 C60 O59 123.6(17) . . ?
O58 C60 C61 121(2) . . ?
O59 C60 C61 114.3(15) . . ?
Cl63 C61 Cl62 109.8(14) . . ?
Cl64 C61 Cl62 112.6(13) . . ?
Cl64 C61 Cl63 113.2(13) . . ?
Cl64 C61 C60 114.9(17) . . ?
C60 C61 Cl62 91.5(13) . . ?
C60 C61 Cl63 112.8(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.746(3)
2 0.254(3)

####################################################################### 
# 
# 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_L5
_database_code_depnum_ccdc_archive 'CCDC 2080283'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
# start Validation Reply Form
_vrf_DIFMX02_L5                  
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: The largest residual Q-peak (Q1) was found 1.31 
angstroms from the atom F72 and no twin law or 
apparent disorder were observed. 
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N2, F6 P'
_chemical_formula_sum            'C18 H15 F6 N2 P'
_chemical_formula_weight         404.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H15 N2 P1 F6'
_chemical_oxdiff_usercomment     ACN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.3513(4)
_cell_length_b                   20.6761(7)
_cell_length_c                   7.9162(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.920(4)
_cell_angle_gamma                90
_cell_volume                     1663.58(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1979
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.1720
_cell_measurement_theta_min      4.2450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78267
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 -1 1 0.0418
6 3 0 0.0180
-2 7 4 0.1065
2 -7 -4 0.1065
-3 -3 5 0.0661
3 4 -5 0.0452
0 13 1 0.1023
0 -13 0 0.1072
-6 -4 -1 0.0593
-6 4 -1 0.0531
2 -10 3 0.0950

_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.075
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-7.0000 -1.0000 1.0000 -0.3695 0.9345 -0.2854
6.0000 3.0000 0.0000 0.3091 -0.8837 0.0268
-2.0000 7.0000 4.0000 -0.0357 -0.0155 -0.9488
2.0000 -7.0000 -4.0000 0.0357 0.0155 0.9488
-3.0000 -3.0000 5.0000 0.5199 0.4902 -0.7468
3.0000 4.0000 -5.0000 -0.5712 -0.5281 0.7084
0.0000 13.0000 1.0000 -0.5478 -0.4946 -0.6572
-0.0000 -13.0000 -0.0000 0.6673 0.4929 0.4990
-6.0000 -4.0000 -1.0000 -0.3773 0.9233 0.1698
-6.0000 4.0000 -1.0000 -0.7879 0.6200 -0.1373
2.0000 -10.0000 3.0000 1.0261 0.1174 -0.0434

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.100
_diffrn_reflns_theta_min         4.277
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -15.00   1.00    1.00    --  -41.65 -57.00 -30.00   98
  2  ω     41.00  78.00   1.00    1.00    --   41.65-125.00 -60.00   37
  3  ω    -37.00  44.00   1.00    1.00    --   41.65 -19.00 150.00   81
  4  ω     81.00 178.00   1.00    3.00    --  112.00  77.00 -60.00   97
  5  ω     34.00 109.00   1.00    3.00    --  112.00 -94.00  30.00   75
  6  ω     64.00 104.00   1.00    3.00    --  112.00 -94.00-180.00   40
  7  ω     44.00 127.00   1.00    3.00    --  112.00 -45.00 150.00   83
  8  ω     58.00 139.00   1.00    3.00    --  112.00 178.00  90.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0771833000
_diffrn_orient_matrix_UB_12      -0.0513293000
_diffrn_orient_matrix_UB_13      0.1194956000
_diffrn_orient_matrix_UB_21      -0.1283302000
_diffrn_orient_matrix_UB_22      -0.0379139000
_diffrn_orient_matrix_UB_23      -0.0016996000
_diffrn_orient_matrix_UB_31      0.0236521000
_diffrn_orient_matrix_UB_32      -0.0383862000
_diffrn_orient_matrix_UB_33      -0.1581976000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             1637
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.343
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0887P)²+5.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1667
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H20A(0.5) H20B(0.5) H20C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C12(H12), C13(H13), C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P70 P 0.5000 0.77951(4) 0.7500 0.0135(3) Uani 1 2 d S T P . .
F72 F 0.5648(2) 0.72502(10) 0.6498(3) 0.0422(5) Uani 1 1 d . . . . .
F75 F 0.56492(19) 0.83432(10) 0.6495(3) 0.0457(6) Uani 1 1 d . . . . .
F76 F 0.37152(18) 0.78008(9) 0.6013(2) 0.0367(5) Uani 1 1 d . . . . .
N10 N 0.5000 0.57548(16) 0.2500 0.0250(7) Uani 1 2 d S T P . .
N17 N 0.5000 0.77623(15) 0.2500 0.0250(7) Uani 1 2 d S T P . .
C4 C 0.4357(3) 0.47074(14) 0.1955(4) 0.0272(6) Uani 1 1 d . . . . .
C5 C 0.3522(3) 0.42105(14) 0.1202(4) 0.0320(7) Uani 1 1 d . . . . .
H5 H 0.3761 0.3779 0.1395 0.038 Uiso 1 1 calc R . . . .
C6 C 0.2340(3) 0.43726(15) 0.0169(4) 0.0343(7) Uani 1 1 d . . . . .
H6 H 0.1770 0.4047 -0.0320 0.041 Uiso 1 1 calc R . . . .
C11 C 0.3975(3) 0.53537(13) 0.1645(4) 0.0257(6) Uani 1 1 d . . . . .
C12 C 0.2802(3) 0.55187(15) 0.0565(4) 0.0298(6) Uani 1 1 d . . . . .
H12 H 0.2572 0.5949 0.0330 0.036 Uiso 1 1 calc R . . . .
C13 C 0.1986(3) 0.50190(16) -0.0152(4) 0.0334(7) Uani 1 1 d . . . . .
H13 H 0.1187 0.5116 -0.0861 0.040 Uiso 1 1 calc R . . . .
C14 C 0.5000 0.64257(19) 0.2500 0.0240(8) Uani 1 2 d S T P . .
C18 C 0.3872(3) 0.74380(14) 0.2503(4) 0.0259(6) Uani 1 1 d . . . . .
H18 H 0.3099 0.7668 0.2500 0.031 Uiso 1 1 calc R . . . .
C19 C 0.3844(3) 0.67755(13) 0.2510(4) 0.0255(6) Uani 1 1 d . . . . .
H19 H 0.3058 0.6559 0.2521 0.031 Uiso 1 1 calc R . . . .
C20 C 0.5000 0.84758(19) 0.2500 0.0313(9) Uani 1 2 d S T P . .
H20A H 0.4202 0.8631 0.1794 0.047 Uiso 0.5 1 calc GR . . A -1
H20B H 0.5741 0.8631 0.2051 0.047 Uiso 0.5 1 calc GR . . A -1
H20C H 0.5056 0.8631 0.3655 0.047 Uiso 0.5 1 calc GR . . A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P70 F72 1.5969(19) 2_656 ?
P70 F72 1.5969(19) . ?
P70 F75 1.6034(19) . ?
P70 F75 1.6033(19) 2_656 ?
P70 F76 1.6005(18) 2_656 ?
P70 F76 1.6005(18) . ?
N10 C11 1.414(3) 2_655 ?
N10 C11 1.414(3) . ?
N10 C14 1.387(5) . ?
N17 C18 1.347(3) . ?
N17 C18 1.347(3) 2_655 ?
N17 C20 1.475(5) . ?
C4 C4 1.442(6) 2_655 ?
C4 C5 1.401(4) . ?
C4 C11 1.402(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(5) . ?
C6 H6 0.9300 . ?
C6 C13 1.396(5) . ?
C11 C12 1.389(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.400(3) 2_655 ?
C14 C19 1.400(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(4) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
F72 P70 F72 90.26(16) 2_656 . ?
F72 P70 F75 179.89(12) 2_656 . ?
F72 P70 F75 89.85(12) . . ?
F72 P70 F75 179.89(13) . 2_656 ?
F72 P70 F75 89.84(12) 2_656 2_656 ?
F72 P70 F76 90.48(10) 2_656 2_656 ?
F72 P70 F76 90.12(11) . 2_656 ?
F72 P70 F76 90.48(10) . . ?
F72 P70 F76 90.12(11) 2_656 . ?
F75 P70 F75 90.05(17) 2_656 . ?
F76 P70 F75 89.52(10) . 2_656 ?
F76 P70 F75 89.88(10) 2_656 2_656 ?
F76 P70 F75 89.52(10) 2_656 . ?
F76 P70 F75 89.88(10) . . ?
F76 P70 F76 179.15(14) 2_656 . ?
C11 N10 C11 108.2(3) . 2_655 ?
C14 N10 C11 125.90(16) . 2_655 ?
C14 N10 C11 125.90(16) . . ?
C18 N17 C18 120.3(3) . 2_655 ?
C18 N17 C20 119.86(17) 2_655 . ?
C18 N17 C20 119.86(17) . . ?
C5 C4 C4 132.81(18) . 2_655 ?
C5 C4 C11 119.5(3) . . ?
C11 C4 C4 107.63(17) . 2_655 ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C13 120.9(3) . . ?
C13 C6 H6 119.5 . . ?
C4 C11 N10 108.3(3) . . ?
C12 C11 N10 129.8(3) . . ?
C12 C11 C4 121.8(3) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 C11 117.5(3) . . ?
C13 C12 H12 121.2 . . ?
C6 C13 H13 119.3 . . ?
C12 C13 C6 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
N10 C14 C19 121.11(18) . . ?
N10 C14 C19 121.11(18) . 2_655 ?
C19 C14 C19 117.8(4) 2_655 . ?
N17 C18 H18 119.4 . . ?
N17 C18 C19 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
N17 C20 H20A 109.5 . . ?
N17 C20 H20B 109.5 . . ?
N17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?


_ins_header                      
;
TITL OHI-114_scale in C2/c 
REM C2/c (#15 in standard setting)
CELL 1.54184  10.351337  20.676078   7.916156  90.0000 100.9201  90.0000
ZERR    3.00   0.000411   0.000705   0.000301   0.0000   0.0039   0.0000
LATT  7
SYMM -x, y,-z+1/2 
SFAC C H N F P
UNIT 54.00 45.00 6.00 18.00 3.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_L1Hc
_database_code_depnum_ccdc_archive 'CCDC 2080287'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L1Hc                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 N2 O, C6 H5 O3 S, C H Cl3'
_chemical_formula_sum            'C37 H27 Cl3 N2 O4 S'
_chemical_formula_weight         702.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7931(3)
_cell_length_b                   10.2392(4)
_cell_length_c                   17.2182(5)
_cell_angle_alpha                89.8210(10)
_cell_angle_beta                 76.475(2)
_cell_angle_gamma                73.060(2)
_cell_volume                     1601.89(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    170
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878
_shelx_estimated_absorpt_T_max   0.943
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.8674.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12863
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.084
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4263
_reflns_number_total             5620
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+3.1384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1300
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C74(H74)
2.b Aromatic/amide H refined with riding coordinates:
 C56(H56), C57(H57), C58(H58), C59(H59), C60(H60), N1(H1), C2(H2), C3(H3),
 C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31),
  C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl71 Cl 0.98010(14) 0.12663(18) -0.11508(10) 0.1044(6) Uani 1 1 d . . . . .
Cl72 Cl 1.07243(15) 0.35068(15) -0.07413(10) 0.0874(5) Uani 1 1 d . . . . .
Cl73 Cl 0.89300(15) 0.2438(2) 0.04608(7) 0.1022(6) Uani 1 1 d . . . . .
C74 C 1.0326(4) 0.2039(4) -0.0417(2) 0.0420(9) Uani 1 1 d . . . . .
H74 H 1.1209 0.1401 -0.0304 0.050 Uiso 1 1 calc R . . . .
S54 S -0.26726(8) 0.83571(8) 0.56990(5) 0.02301(19) Uani 1 1 d . . . . .
O51 O -0.1685(2) 0.9020(2) 0.59493(13) 0.0289(5) Uani 1 1 d . . . . .
O52 O -0.1960(2) 0.6905(2) 0.55105(14) 0.0351(6) Uani 1 1 d . . . . .
O53 O -0.3310(2) 0.9064(2) 0.50787(12) 0.0278(5) Uani 1 1 d . . . . .
C55 C -0.4180(3) 0.8527(3) 0.65423(18) 0.0234(7) Uani 1 1 d . . . . .
C56 C -0.3984(4) 0.7702(3) 0.71711(19) 0.0296(8) Uani 1 1 d . . . . .
H56 H -0.3084 0.7046 0.7141 0.036 Uiso 1 1 calc R . . . .
C57 C -0.5128(4) 0.7856(4) 0.7843(2) 0.0351(8) Uani 1 1 d . . . . .
H57 H -0.4994 0.7309 0.8267 0.042 Uiso 1 1 calc R . . . .
C58 C -0.6476(4) 0.8828(4) 0.7884(2) 0.0394(9) Uani 1 1 d . . . . .
H58 H -0.7242 0.8941 0.8339 0.047 Uiso 1 1 calc R . . . .
C59 C -0.6675(4) 0.9624(4) 0.7249(2) 0.0405(9) Uani 1 1 d . . . . .
H59 H -0.7582 1.0265 0.7273 0.049 Uiso 1 1 calc R . . . .
C60 C -0.5526(3) 0.9475(4) 0.6570(2) 0.0321(8) Uani 1 1 d . . . . .
H60 H -0.5664 1.0008 0.6140 0.038 Uiso 1 1 calc R . . . .
O27 O 1.3436(3) -0.0322(2) -0.01199(13) 0.0346(6) Uani 1 1 d . . . . .
N1 N 0.1192(3) 0.7482(3) 0.52373(16) 0.0277(6) Uani 1 1 d . . . . .
H1 H 0.0102 0.7887 0.5555 0.033 Uiso 1 1 calc R . . . .
N11 N 0.9967(3) 0.4534(3) 0.25536(15) 0.0255(6) Uani 1 1 d . . . . .
C2 C 0.1686(4) 0.6175(3) 0.49447(19) 0.0294(8) Uani 1 1 d . . . . .
H2 H 0.1051 0.5639 0.5027 0.035 Uiso 1 1 calc R . . . .
C3 C 0.3112(3) 0.5620(3) 0.45266(19) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.3441 0.4706 0.4335 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4086(3) 0.6409(3) 0.43826(18) 0.0229(7) Uani 1 1 d . . . . .
C5 C 0.3527(3) 0.7761(3) 0.4709(2) 0.0305(8) Uani 1 1 d . . . . .
H5 H 0.4141 0.8317 0.4642 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2088(4) 0.8280(3) 0.5126(2) 0.0310(8) Uani 1 1 d . . . . .
H6 H 0.1729 0.9186 0.5333 0.037 Uiso 1 1 calc R . . . .
C7 C 0.5622(3) 0.5853(3) 0.39024(18) 0.0230(7) Uani 1 1 d . . . . .
C8 C 0.6102(3) 0.4581(3) 0.34546(19) 0.0277(7) Uani 1 1 d . . . . .
H8 H 0.5437 0.4086 0.3469 0.033 Uiso 1 1 calc R . . . .
C9 C 0.7521(3) 0.4046(3) 0.29971(19) 0.0266(7) Uani 1 1 d . . . . .
H9 H 0.7816 0.3203 0.2709 0.032 Uiso 1 1 calc R . . . .
C10 C 0.8505(3) 0.4805(3) 0.29782(18) 0.0238(7) Uani 1 1 d . . . . .
C12 C 1.0459(3) 0.5639(3) 0.27240(18) 0.0244(7) Uani 1 1 d . . . . .
C13 C 1.1851(3) 0.5819(3) 0.24665(19) 0.0287(7) Uani 1 1 d . . . . .
H13 H 1.2618 0.5169 0.2120 0.034 Uiso 1 1 calc R . . . .
C14 C 1.2042(4) 0.7001(3) 0.27466(19) 0.0305(8) Uani 1 1 d . . . . .
H14 H 1.2959 0.7145 0.2583 0.037 Uiso 1 1 calc R . . . .
C15 C 1.0905(3) 0.7984(3) 0.32663(19) 0.0285(7) Uani 1 1 d . . . . .
H15 H 1.1068 0.8772 0.3439 0.034 Uiso 1 1 calc R . . . .
C16 C 0.9536(3) 0.7792(3) 0.35260(18) 0.0263(7) Uani 1 1 d . . . . .
H16 H 0.8776 0.8443 0.3876 0.032 Uiso 1 1 calc R . . . .
C17 C 0.9314(3) 0.6605(3) 0.32548(18) 0.0226(7) Uani 1 1 d . . . . .
C18 C 0.8057(3) 0.6076(3) 0.34172(18) 0.0221(7) Uani 1 1 d . . . . .
C19 C 0.6623(3) 0.6596(3) 0.38793(18) 0.0230(7) Uani 1 1 d . . . . .
H19 H 0.6330 0.7435 0.4172 0.028 Uiso 1 1 calc R . . . .
C20 C 1.0831(3) 0.3323(3) 0.20675(18) 0.0255(7) Uani 1 1 d . . . . .
C21 C 1.0864(3) 0.2049(3) 0.23628(19) 0.0262(7) Uani 1 1 d . . . . .
H21 H 1.0297 0.1990 0.2869 0.031 Uiso 1 1 calc R . . . .
C22 C 1.1744(3) 0.0870(3) 0.18982(18) 0.0263(7) Uani 1 1 d . . . . .
H22 H 1.1785 0.0020 0.2100 0.032 Uiso 1 1 calc R . . . .
C23 C 1.2566(3) 0.0945(3) 0.11326(18) 0.0249(7) Uani 1 1 d . . . . .
C24 C 1.2523(3) 0.2222(3) 0.08421(19) 0.0278(7) Uani 1 1 d . . . . .
H24 H 1.3072 0.2279 0.0331 0.033 Uiso 1 1 calc R . . . .
C25 C 1.1671(3) 0.3407(3) 0.13077(19) 0.0280(7) Uani 1 1 d . . . . .
H25 H 1.1660 0.4258 0.1113 0.034 Uiso 1 1 calc R . . . .
C26 C 1.3408(3) -0.0317(3) 0.05955(19) 0.0261(7) Uani 1 1 d . . . . .
C28 C 1.4206(3) -0.1562(3) 0.09414(18) 0.0261(7) Uani 1 1 d . . . . .
C29 C 1.4869(3) -0.1462(4) 0.15625(19) 0.0311(8) Uani 1 1 d . . . . .
H29 H 1.4765 -0.0608 0.1794 0.037 Uiso 1 1 calc R . . . .
C30 C 1.5687(4) -0.2640(4) 0.1834(2) 0.0397(9) Uani 1 1 d . . . . .
H30 H 1.6150 -0.2577 0.2240 0.048 Uiso 1 1 calc R . . . .
C31 C 1.5812(4) -0.3906(4) 0.1502(2) 0.0455(10) Uani 1 1 d . . . . .
H31 H 1.6355 -0.4695 0.1687 0.055 Uiso 1 1 calc R . . . .
C32 C 1.5141(4) -0.4007(4) 0.0899(2) 0.0432(9) Uani 1 1 d . . . . .
H32 H 1.5221 -0.4865 0.0684 0.052 Uiso 1 1 calc R . . . .
C33 C 1.4350(4) -0.2848(4) 0.0610(2) 0.0344(8) Uani 1 1 d . . . . .
H33 H 1.3913 -0.2925 0.0194 0.041 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl71 C74 1.742(4) . ?
Cl72 C74 1.719(4) . ?
Cl73 C74 1.742(4) . ?
C74 H74 0.9800 . ?
S54 O51 1.470(2) . ?
S54 O52 1.448(2) . ?
S54 O53 1.449(2) . ?
S54 C55 1.780(3) . ?
C55 C56 1.385(4) . ?
C55 C60 1.381(4) . ?
C56 H56 0.9300 . ?
C56 C57 1.381(5) . ?
C57 H57 0.9300 . ?
C57 C58 1.389(5) . ?
C58 H58 0.9300 . ?
C58 C59 1.379(5) . ?
C59 H59 0.9300 . ?
C59 C60 1.393(5) . ?
C60 H60 0.9300 . ?
O27 C26 1.226(4) . ?
N1 H1 1.0400 . ?
N1 C2 1.339(4) . ?
N1 C6 1.346(4) . ?
N11 C10 1.394(4) . ?
N11 C12 1.409(4) . ?
N11 C20 1.420(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.401(4) . ?
C4 C5 1.397(4) . ?
C4 C7 1.481(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.411(4) . ?
C7 C19 1.400(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.398(4) . ?
C10 C18 1.405(4) . ?
C12 C13 1.397(4) . ?
C12 C17 1.397(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.393(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.396(4) . ?
C17 C18 1.454(4) . ?
C18 C19 1.390(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(4) . ?
C20 C25 1.390(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.390(4) . ?
C23 C24 1.391(4) . ?
C23 C26 1.495(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(5) . ?
C25 H25 0.9300 . ?
C26 C28 1.491(4) . ?
C28 C29 1.393(4) . ?
C28 C33 1.392(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.387(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(5) . ?
C31 H31 0.9300 . ?
C31 C32 1.370(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.377(5) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl71 C74 H74 108.8 . . ?
Cl72 C74 Cl71 110.6(2) . . ?
Cl72 C74 Cl73 109.4(2) . . ?
Cl72 C74 H74 108.8 . . ?
Cl73 C74 Cl71 110.4(2) . . ?
Cl73 C74 H74 108.8 . . ?
O51 S54 C55 106.52(13) . . ?
O52 S54 O51 110.95(13) . . ?
O52 S54 O53 114.51(14) . . ?
O52 S54 C55 106.75(14) . . ?
O53 S54 O51 112.04(13) . . ?
O53 S54 C55 105.45(14) . . ?
C56 C55 S54 119.2(2) . . ?
C60 C55 S54 120.3(2) . . ?
C60 C55 C56 120.5(3) . . ?
C55 C56 H56 120.0 . . ?
C57 C56 C55 119.9(3) . . ?
C57 C56 H56 120.0 . . ?
C56 C57 H57 120.0 . . ?
C56 C57 C58 120.0(3) . . ?
C58 C57 H57 120.0 . . ?
C57 C58 H58 120.1 . . ?
C59 C58 C57 119.8(3) . . ?
C59 C58 H58 120.1 . . ?
C58 C59 H59 119.8 . . ?
C58 C59 C60 120.4(3) . . ?
C60 C59 H59 119.8 . . ?
C55 C60 C59 119.3(3) . . ?
C55 C60 H60 120.4 . . ?
C59 C60 H60 120.4 . . ?
C2 N1 H1 119.6 . . ?
C2 N1 C6 120.9(3) . . ?
C6 N1 H1 119.6 . . ?
C10 N11 C12 108.0(3) . . ?
C10 N11 C20 125.9(2) . . ?
C12 N11 C20 126.0(2) . . ?
N1 C2 H2 119.7 . . ?
N1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 122.1(3) . . ?
C5 C4 C3 116.4(3) . . ?
C5 C4 C7 121.5(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 120.2(3) . . ?
N1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C4 121.1(3) . . ?
C19 C7 C4 120.1(3) . . ?
C19 C7 C8 118.8(3) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.3(3) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.2(3) . . ?
C10 C9 H9 120.9 . . ?
N11 C10 C9 130.2(3) . . ?
N11 C10 C18 109.0(3) . . ?
C9 C10 C18 120.8(3) . . ?
C13 C12 N11 129.5(3) . . ?
C17 C12 N11 109.2(3) . . ?
C17 C12 C13 121.2(3) . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.4(3) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 H14 119.0 . . ?
C13 C14 C15 122.0(3) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.9(3) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C18 106.7(3) . . ?
C16 C17 C12 120.1(3) . . ?
C16 C17 C18 133.1(3) . . ?
C10 C18 C17 107.0(3) . . ?
C19 C18 C10 120.3(3) . . ?
C19 C18 C17 132.7(3) . . ?
C7 C19 H19 120.1 . . ?
C18 C19 C7 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C21 C20 N11 119.7(3) . . ?
C25 C20 N11 120.2(3) . . ?
C25 C20 C21 120.1(3) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(3) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 C26 121.2(3) . . ?
C24 C23 C26 119.4(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.1 . . ?
C24 C25 C20 119.8(3) . . ?
C24 C25 H25 120.1 . . ?
O27 C26 C23 120.1(3) . . ?
O27 C26 C28 120.7(3) . . ?
C28 C26 C23 119.2(3) . . ?
C29 C28 C26 121.3(3) . . ?
C33 C28 C26 119.2(3) . . ?
C33 C28 C29 119.5(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 C28 119.7(3) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C30 C31 H31 119.8 . . ?
C32 C31 C30 120.4(4) . . ?
C32 C31 H31 119.8 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.5(4) . . ?
C33 C32 H32 119.7 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.9(3) . . ?
C32 C33 H33 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L4Hd
_database_code_depnum_ccdc_archive 'CCDC 2080293'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7

# start Validation Reply Form
_vrf_PLAT353_L4Hd                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2, C2 H Cl2 O2'
_chemical_formula_sum            'C25 H18 Cl2 N2 O2'
_chemical_formula_weight         449.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.8180(9)
_cell_length_b                   10.5771(8)
_cell_length_c                   21.7225(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4093.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    170
_cell_measurement_reflns_used    4958
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1007 before and 0.0748 after correction.
The Ratio of minimum to maximum transmission is 0.6729.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0852
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21176
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.875
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2727
_reflns_number_total             4510
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.245
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1166P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1924
_refine_ls_wR_factor_ref         0.2204
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C96(H96)
2.b Aromatic/amide H refined with riding coordinates:
 N23(H23), C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl93 Cl 0.17833(6) 0.69905(11) 0.75893(5) 0.0496(3) Uani 1 1 d . . . . .
Cl94 Cl 0.16749(7) 0.92874(11) 0.68697(5) 0.0531(3) Uani 1 1 d . . . . .
O91 O 0.18033(15) 0.6470(3) 0.62399(14) 0.0527(8) Uani 1 1 d . . . . .
O92 O 0.06034(17) 0.7028(3) 0.61503(14) 0.0560(9) Uani 1 1 d . . . . .
N10 N 0.06426(16) -0.2552(3) 0.38907(14) 0.0326(7) Uani 1 1 d . . . . .
N23 N 0.14763(17) 0.4420(3) 0.56394(15) 0.0386(8) Uani 1 1 d . . . . .
H23 H 0.1595 0.5272 0.5858 0.046 Uiso 1 1 calc R . . . .
C1 C -0.1016(2) -0.3818(4) 0.27039(19) 0.0416(10) Uani 1 1 d . . . . .
H1 H -0.1387 -0.4151 0.2435 0.050 Uiso 1 1 calc R . . . .
C2 C -0.0400(2) -0.4548(4) 0.28657(18) 0.0382(9) Uani 1 1 d . . . . .
H2 H -0.0343 -0.5375 0.2702 0.046 Uiso 1 1 calc R . . . .
C3 C 0.01333(19) -0.4064(4) 0.32674(17) 0.0320(9) Uani 1 1 d . . . . .
C4 C 0.0814(2) -0.4565(4) 0.35302(17) 0.0335(9) Uani 1 1 d . . . . .
C5 C 0.1191(2) -0.5706(4) 0.34593(19) 0.0410(10) Uani 1 1 d . . . . .
H5 H 0.0986 -0.6361 0.3212 0.049 Uiso 1 1 calc R . . . .
C6 C 0.1875(2) -0.5871(4) 0.3758(2) 0.0459(11) Uani 1 1 d . . . . .
H6 H 0.2140 -0.6645 0.3714 0.055 Uiso 1 1 calc R . . . .
C7 C 0.2174(2) -0.4910(4) 0.4121(2) 0.0440(10) Uani 1 1 d . . . . .
H7 H 0.2647 -0.5036 0.4314 0.053 Uiso 1 1 calc R . . . .
C8 C 0.1804(2) -0.3784(4) 0.4208(2) 0.0399(9) Uani 1 1 d . . . . .
H8 H 0.2011 -0.3141 0.4462 0.048 Uiso 1 1 calc R . . . .
C9 C 0.11154(19) -0.3615(4) 0.39124(17) 0.0327(8) Uani 1 1 d . . . . .
C11 C 0.00469(19) -0.2828(4) 0.34899(17) 0.0323(9) Uani 1 1 d . . . . .
C12 C -0.0568(2) -0.2078(4) 0.33276(18) 0.0370(9) Uani 1 1 d . . . . .
H12 H -0.0624 -0.1243 0.3481 0.044 Uiso 1 1 calc R . . . .
C13 C -0.1092(2) -0.2606(4) 0.29342(19) 0.0402(9) Uani 1 1 d . . . . .
H13 H -0.1518 -0.2120 0.2818 0.048 Uiso 1 1 calc R . . . .
C14 C 0.07652(18) -0.1386(4) 0.41897(17) 0.0315(8) Uani 1 1 d . . . . .
C15 C 0.0960(2) -0.1341(4) 0.48084(18) 0.0354(9) Uani 1 1 d . . . . .
H15 H 0.1009 -0.2102 0.5037 0.043 Uiso 1 1 calc R . . . .
C16 C 0.10827(19) -0.0194(4) 0.50904(18) 0.0346(9) Uani 1 1 d . . . . .
H16 H 0.1227 -0.0172 0.5511 0.041 Uiso 1 1 calc R . . . .
C17 C 0.09978(19) 0.0939(4) 0.47667(17) 0.0321(9) Uani 1 1 d . . . . .
C18 C 0.07797(19) 0.0890(4) 0.41543(18) 0.0346(9) Uani 1 1 d . . . . .
H18 H 0.0697 0.1652 0.3933 0.041 Uiso 1 1 calc R . . . .
C19 C 0.0682(2) -0.0259(4) 0.38661(18) 0.0351(9) Uani 1 1 d . . . . .
H19 H 0.0557 -0.0282 0.3441 0.042 Uiso 1 1 calc R . . . .
C20 C 0.11566(19) 0.2160(4) 0.50666(17) 0.0351(9) Uani 1 1 d . . . . .
C21 C 0.1754(2) 0.2283(4) 0.54812(18) 0.0393(10) Uani 1 1 d . . . . .
H21 H 0.2059 0.1570 0.5571 0.047 Uiso 1 1 calc R . . . .
C22 C 0.1902(2) 0.3407(4) 0.57574(19) 0.0439(10) Uani 1 1 d . . . . .
H22 H 0.2311 0.3475 0.6036 0.053 Uiso 1 1 calc R . . . .
C24 C 0.0903(2) 0.4356(4) 0.52463(19) 0.0411(10) Uani 1 1 d . . . . .
H24 H 0.0607 0.5087 0.5169 0.049 Uiso 1 1 calc R . . . .
C25 C 0.07345(19) 0.3240(4) 0.49511(18) 0.0369(9) Uani 1 1 d . . . . .
H25 H 0.0329 0.3207 0.4668 0.044 Uiso 1 1 calc R . . . .
C95 C 0.1217(2) 0.7027(4) 0.64091(19) 0.0393(9) Uani 1 1 d . . . . .
C96 C 0.1262(2) 0.7783(4) 0.70159(18) 0.0403(10) Uani 1 1 d . . . . .
H96 H 0.0740 0.7918 0.7173 0.048 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl93 C96 1.766(4) . ?
Cl94 C96 1.782(4) . ?
O91 C95 1.254(5) . ?
O92 C95 1.230(5) . ?
N10 C9 1.406(5) . ?
N10 C11 1.403(5) . ?
N10 C14 1.411(5) . ?
N23 H23 1.0400 . ?
N23 C22 1.337(5) . ?
N23 C24 1.334(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(5) . ?
C1 C13 1.382(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 C4 1.441(5) . ?
C3 C11 1.403(5) . ?
C4 C5 1.390(5) . ?
C4 C9 1.410(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.392(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.373(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.397(5) . ?
C11 C12 1.398(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(5) . ?
C14 C19 1.392(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(5) . ?
C17 C18 1.387(5) . ?
C17 C20 1.474(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(5) . ?
C20 C25 1.391(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.358(6) . ?
C22 H22 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.376(5) . ?
C25 H25 0.9500 . ?
C95 C96 1.544(6) . ?
C96 H96 1.0000 . ?

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
C9 N10 C14 126.2(3) . . ?
C11 N10 C9 107.9(3) . . ?
C11 N10 C14 125.8(3) . . ?
C22 N23 H23 119.4 . . ?
C24 N23 H23 119.4 . . ?
C24 N23 C22 121.1(4) . . ?
C2 C1 H1 120.0 . . ?
C13 C1 H1 120.0 . . ?
C13 C1 C2 120.1(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 133.6(4) . . ?
C2 C3 C11 119.0(3) . . ?
C11 C3 C4 107.4(3) . . ?
C5 C4 C3 133.0(4) . . ?
C5 C4 C9 120.0(4) . . ?
C9 C4 C3 107.0(3) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(4) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.5(4) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 118.0(4) . . ?
C9 C8 H8 121.0 . . ?
N10 C9 C4 108.8(3) . . ?
C8 C9 N10 130.2(4) . . ?
C8 C9 C4 120.9(4) . . ?
C3 C11 N10 108.9(3) . . ?
C12 C11 N10 129.2(4) . . ?
C12 C11 C3 121.9(3) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.1(4) . . ?
C13 C12 H12 121.4 . . ?
C1 C13 C12 122.1(4) . . ?
C1 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C15 C14 N10 120.9(4) . . ?
C15 C14 C19 119.1(4) . . ?
C19 C14 N10 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C20 120.5(3) . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 C20 120.7(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C17 120.8(3) . . ?
C25 C20 C17 122.4(3) . . ?
C25 C20 C21 116.8(4) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(4) . . ?
C22 C21 H21 119.5 . . ?
N23 C22 C21 120.4(4) . . ?
N23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
N23 C24 H24 119.7 . . ?
N23 C24 C25 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.2(4) . . ?
C24 C25 H25 119.9 . . ?
O91 C95 C96 116.8(3) . . ?
O92 C95 O91 127.4(4) . . ?
O92 C95 C96 115.8(4) . . ?
Cl93 C96 Cl94 109.4(2) . . ?
Cl93 C96 H96 108.5 . . ?
Cl94 C96 H96 108.5 . . ?
C95 C96 Cl93 112.6(3) . . ?
C95 C96 Cl94 109.3(3) . . ?
C95 C96 H96 108.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L4Hb
_database_code_depnum_ccdc_archive 'CCDC 2080291'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L4Hb                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N2, C2 Cl3 O2'
_chemical_formula_sum            'C25 H17 Cl3 N2 O2'
_chemical_formula_weight         483.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H17 N2 O2 Cl3'
_chemical_oxdiff_usercomment     CHCl3/DIPE
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4592(2)
_cell_length_b                   18.8630(3)
_cell_length_c                   22.0371(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.284(2)
_cell_angle_gamma                90
_cell_volume                     4302.38(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11133
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.1940
_cell_measurement_theta_min      3.0480
_shelx_estimated_absorpt_T_max   0.854
_shelx_estimated_absorpt_T_min   0.286
_exptl_absorpt_coefficient_mu    4.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.554
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 12 3 0.0469
0 -12 -3 0.0633
-6 -2 -3 0.1738
6 -4 2 0.1854
4 9 4 0.0996
0 0 -14 0.0199
0 0 14 0.0199

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 12.0000 2.9998 -0.0521 -0.1801 0.9853
-0.0001 -12.0000 -2.9998 0.0521 0.1801 -0.9853
-6.0000 -2.0000 -2.9998 0.2102 0.9365 -0.0535
6.0000 -4.0000 1.9998 -0.2188 -0.8512 -0.4342
4.0001 9.0000 3.9997 -0.1792 -0.7401 0.6660
-0.0001 -0.0000 -13.9997 0.9699 0.1344 -0.1367
0.0001 0.0000 13.9997 -0.9699 -0.1344 0.1367

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            30480
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.500
_diffrn_reflns_theta_min         3.098
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -16.00   1.00    1.50    --  -42.32 -57.00   0.00   96
  2  ω    -59.00  31.00   1.00    1.50    --  -42.32  77.00-150.00   90
  3  ω   -112.00 -18.00   1.00    1.50    --  -42.32 -57.00  90.00   94
  4  ω      1.00  82.00   1.00    1.50    --   42.32 -99.00 -30.00   81
  5  ω     83.00 178.00   1.00    3.00    --  111.00  61.00 120.00   95
  6  ω     87.00 178.00   1.00    3.00    --  111.00  30.00  90.00   91
  7  ω     83.00 116.00   1.00    3.00    --  111.00-111.00  60.00   33
  8  ω     45.00 127.00   1.00    3.00    --  111.00 -77.00-180.00   82
  9  ω     83.00 109.00   1.00    3.00    --  111.00 -94.00 150.00   26
 10  ω     36.00  63.00   1.00    3.00    --  111.00-111.00  60.00   27
 11  ω     75.00 136.00   1.00    3.00    --  111.00 -77.00  60.00   61
 12  ω     87.00 177.00   1.00    3.00    --  111.00  45.00-180.00   90
 13  ω     41.00 127.00   1.00    3.00    --  111.00 -30.00 150.00   86
 14  ω     40.00 116.00   1.00    3.00    --  111.00-111.00 -30.00   76
 15  ω     37.00  65.00   1.00    3.00    --  111.00 -94.00 150.00   28
 16  ω     41.00 136.00   1.00    3.00    --  111.00 -61.00 -30.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047187000
_diffrn_orient_matrix_UB_12      0.0129772000
_diffrn_orient_matrix_UB_13      -0.0692814000
_diffrn_orient_matrix_UB_21      -0.1470759000
_diffrn_orient_matrix_UB_22      -0.0126040000
_diffrn_orient_matrix_UB_23      -0.0095985000
_diffrn_orient_matrix_UB_31      -0.0225155000
_diffrn_orient_matrix_UB_32      0.0796651000
_diffrn_orient_matrix_UB_33      0.0097637000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7474
_reflns_number_total             8759
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.962
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         8759
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+11.4894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1555
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C85-Cl80
 1.77 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(N48) \\sim Ueq, Uanis(C47) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 C85, Cl84, Cl83, Cl81, Cl80
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(Cl80)=Sof(Cl83)=1-FVAR(1)
 Sof(Cl81)=Sof(Cl84)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N23(H23), N48(H48), C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C24(H24),
  C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C33(H33),
 C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47),
  C49(H49), C50(H50)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl73 Cl 0.76315(8) 0.42855(4) 0.28685(4) 0.03157(19) Uani 1 1 d . . . . .
Cl74 Cl 0.89230(7) 0.30463(4) 0.34222(4) 0.03042(19) Uani 1 1 d . . . . .
Cl75 Cl 0.64752(8) 0.29127(5) 0.26469(4) 0.0331(2) Uani 1 1 d . . . . .
Cl80 Cl 0.1551(13) 0.1823(7) 0.2615(5) 0.046(2) Uani 0.201(14) 1 d D U P A 2
Cl81 Cl 0.1713(3) 0.1638(3) 0.25041(12) 0.0462(8) Uani 0.799(14) 1 d . U P A 1
Cl82 Cl 0.40012(7) 0.18586(4) 0.33776(4) 0.02623(18) Uani 1 1 d . . . . .
Cl83 Cl 0.2725(11) 0.0581(6) 0.2896(10) 0.054(3) Uani 0.201(14) 1 d . U P A 2
Cl84 Cl 0.2976(3) 0.04572(11) 0.3189(2) 0.0433(8) Uani 0.799(14) 1 d . U P A 1
O71 O 0.6184(2) 0.29969(14) 0.39619(12) 0.0360(6) Uani 1 1 d . . . . .
O72 O 0.6766(2) 0.41384(14) 0.40366(11) 0.0354(6) Uani 1 1 d . . . . .
O78 O 0.1634(3) 0.09745(17) 0.41004(12) 0.0426(7) Uani 1 1 d . . . . .
O79 O 0.1232(3) 0.20780(14) 0.37738(14) 0.0427(7) Uani 1 1 d . . . . .
N10 N -0.2235(2) 0.45150(15) 0.62011(12) 0.0243(6) Uani 1 1 d . . . . .
N23 N 0.4360(3) 0.34909(16) 0.45878(13) 0.0291(6) Uani 1 1 d . . . . .
H23 H 0.5162 0.3343 0.4388 0.035 Uiso 1 1 calc R . . . .
N35 N -0.7272(3) 0.08231(17) 0.62117(14) 0.0322(7) Uani 1 1 d . . . . .
N48 N -0.0360(3) 0.12010(18) 0.47001(15) 0.0384(7) Uani 1 1 d . U . . .
H48 H 0.0488 0.1199 0.4505 0.046 Uiso 1 1 calc R . . . .
C1 C -0.5388(3) 0.3317(2) 0.65229(17) 0.0359(8) Uani 1 1 d . . . . .
H1 H -0.6106 0.3066 0.6610 0.043 Uiso 1 1 calc R . . . .
C2 C -0.5210(3) 0.4005(2) 0.67210(16) 0.0312(7) Uani 1 1 d . . . . .
H2 H -0.5797 0.4220 0.6942 0.037 Uiso 1 1 calc R . . . .
C3 C -0.4129(3) 0.43790(19) 0.65846(14) 0.0265(7) Uani 1 1 d . . . . .
C4 C -0.3640(3) 0.50815(19) 0.67388(14) 0.0254(7) Uani 1 1 d . . . . .
C5 C -0.4083(3) 0.5654(2) 0.70526(15) 0.0296(7) Uani 1 1 d . . . . .
H5 H -0.4858 0.5622 0.7211 0.036 Uiso 1 1 calc R . . . .
C6 C -0.3360(3) 0.6265(2) 0.71255(16) 0.0316(7) Uani 1 1 d . . . . .
H6 H -0.3651 0.6645 0.7337 0.038 Uiso 1 1 calc R . . . .
C7 C -0.2190(3) 0.63259(19) 0.68855(16) 0.0305(7) Uani 1 1 d . . . . .
H7 H -0.1718 0.6745 0.6939 0.037 Uiso 1 1 calc R . . . .
C8 C -0.1732(3) 0.57666(18) 0.65692(15) 0.0274(7) Uani 1 1 d . . . . .
H8 H -0.0963 0.5805 0.6406 0.033 Uiso 1 1 calc R . . . .
C9 C -0.2462(3) 0.51429(18) 0.65023(14) 0.0234(6) Uani 1 1 d . . . . .
C11 C -0.3247(3) 0.40402(18) 0.62530(15) 0.0248(6) Uani 1 1 d . . . . .
C12 C -0.3422(3) 0.3346(2) 0.60528(16) 0.0303(7) Uani 1 1 d . . . . .
H12 H -0.2836 0.3128 0.5833 0.036 Uiso 1 1 calc R . . . .
C13 C -0.4504(3) 0.2987(2) 0.61918(17) 0.0344(8) Uani 1 1 d . . . . .
H13 H -0.4644 0.2520 0.6063 0.041 Uiso 1 1 calc R . . . .
C14 C -0.1126(3) 0.43659(17) 0.59230(14) 0.0225(6) Uani 1 1 d . . . . .
C15 C 0.0099(3) 0.45157(18) 0.62357(15) 0.0254(7) Uani 1 1 d . . . . .
H15 H 0.0187 0.4703 0.6630 0.031 Uiso 1 1 calc R . . . .
C16 C 0.1186(3) 0.43862(18) 0.59609(15) 0.0250(7) Uani 1 1 d . . . . .
H16 H 0.1998 0.4507 0.6165 0.030 Uiso 1 1 calc R . . . .
C17 C 0.1077(3) 0.40761(17) 0.53810(14) 0.0222(6) Uani 1 1 d . . . . .
C18 C -0.0160(3) 0.39394(18) 0.50652(14) 0.0253(7) Uani 1 1 d . . . . .
H18 H -0.0247 0.3745 0.4674 0.030 Uiso 1 1 calc R . . . .
C19 C -0.1253(3) 0.40900(18) 0.53283(15) 0.0251(7) Uani 1 1 d . . . . .
H19 H -0.2069 0.4008 0.5110 0.030 Uiso 1 1 calc R . . . .
C20 C 0.2238(3) 0.38847(17) 0.51067(14) 0.0223(6) Uani 1 1 d . . . . .
C21 C 0.3360(3) 0.42928(17) 0.51990(15) 0.0242(6) Uani 1 1 d . . . . .
H21 H 0.3401 0.4699 0.5440 0.029 Uiso 1 1 calc R . . . .
C22 C 0.4412(3) 0.40836(19) 0.49270(16) 0.0287(7) Uani 1 1 d . . . . .
H22 H 0.5161 0.4356 0.4980 0.034 Uiso 1 1 calc R . . . .
C24 C 0.3305(3) 0.3089(2) 0.45014(16) 0.0336(8) Uani 1 1 d . . . . .
H24 H 0.3299 0.2679 0.4267 0.040 Uiso 1 1 calc R . . . .
C25 C 0.2229(3) 0.32712(19) 0.47525(15) 0.0280(7) Uani 1 1 d . . . . .
H25 H 0.1494 0.2988 0.4688 0.034 Uiso 1 1 calc R . . . .
C26 C -0.8463(4) -0.0919(2) 0.71273(17) 0.0377(9) Uani 1 1 d . . . . .
H26 H -0.8771 -0.1300 0.7332 0.045 Uiso 1 1 calc R . . . .
C27 C -0.9158(3) -0.0292(2) 0.70644(16) 0.0326(8) Uani 1 1 d . . . . .
H27 H -0.9929 -0.0251 0.7225 0.039 Uiso 1 1 calc R . . . .
C28 C -0.8687(3) 0.0279(2) 0.67560(15) 0.0301(7) Uani 1 1 d . . . . .
C29 C -0.9130(3) 0.0994(2) 0.66222(15) 0.0299(7) Uani 1 1 d . . . . .
C30 C -1.0175(3) 0.1392(2) 0.67636(16) 0.0349(8) Uani 1 1 d . . . . .
H30 H -1.0760 0.1194 0.6996 0.042 Uiso 1 1 calc R . . . .
C31 C -1.0333(4) 0.2084(2) 0.65553(18) 0.0394(9) Uani 1 1 d . . . . .
H31 H -1.1031 0.2349 0.6646 0.047 Uiso 1 1 calc R . . . .
C32 C -0.9450(4) 0.2389(2) 0.62097(18) 0.0395(9) Uani 1 1 d . . . . .
H32 H -0.9576 0.2853 0.6071 0.047 Uiso 1 1 calc R . . . .
C33 C -0.8392(3) 0.2012(2) 0.60704(17) 0.0351(8) Uani 1 1 d . . . . .
H33 H -0.7805 0.2216 0.5843 0.042 Uiso 1 1 calc R . . . .
C34 C -0.8236(3) 0.1316(2) 0.62814(16) 0.0314(8) Uani 1 1 d . . . . .
C36 C -0.7527(3) 0.0194(2) 0.65096(15) 0.0301(7) Uani 1 1 d . . . . .
C37 C -0.6815(4) -0.0429(2) 0.65718(17) 0.0364(8) Uani 1 1 d . . . . .
H37 H -0.6046 -0.0472 0.6410 0.044 Uiso 1 1 calc R . . . .
C38 C -0.7298(4) -0.0985(2) 0.68859(18) 0.0387(9) Uani 1 1 d . . . . .
H38 H -0.6840 -0.1409 0.6937 0.046 Uiso 1 1 calc R . . . .
C39 C -0.6123(3) 0.0952(2) 0.59515(16) 0.0305(7) Uani 1 1 d . . . . .
C40 C -0.6173(3) 0.1067(2) 0.53290(17) 0.0383(9) Uani 1 1 d . . . . .
H40 H -0.6967 0.1082 0.5078 0.046 Uiso 1 1 calc R . . . .
C41 C -0.5042(4) 0.1161(2) 0.50788(16) 0.0388(9) Uani 1 1 d . . . . .
H41 H -0.5083 0.1251 0.4662 0.047 Uiso 1 1 calc R . . . .
C42 C -0.3848(3) 0.11204(18) 0.54481(15) 0.0263(7) Uani 1 1 d . . . . .
C43 C -0.3816(3) 0.1034(2) 0.60797(17) 0.0376(9) Uani 1 1 d . . . . .
H43 H -0.3027 0.1029 0.6335 0.045 Uiso 1 1 calc R . . . .
C44 C -0.4949(3) 0.0957(2) 0.63284(17) 0.0377(9) Uani 1 1 d . . . . .
H44 H -0.4919 0.0909 0.6750 0.045 Uiso 1 1 calc R . . . .
C45 C -0.2628(3) 0.11733(18) 0.51838(15) 0.0256(7) Uani 1 1 d . . . . .
C46 C -0.2502(4) 0.1624(2) 0.47008(16) 0.0354(8) Uani 1 1 d . . . . .
H46 H -0.3170 0.1925 0.4540 0.042 Uiso 1 1 calc R . . . .
C47 C -0.1322(4) 0.1611(2) 0.44619(19) 0.0429(9) Uani 1 1 d . U . . .
H47 H -0.1221 0.1897 0.4129 0.051 Uiso 1 1 calc R . . . .
C49 C -0.0441(4) 0.0792(2) 0.51801(19) 0.0368(8) Uani 1 1 d . . . . .
H49 H 0.0271 0.0526 0.5350 0.044 Uiso 1 1 calc R . . . .
C50 C -0.1563(3) 0.07573(19) 0.54274(18) 0.0328(8) Uani 1 1 d . . . . .
H50 H -0.1623 0.0458 0.5758 0.039 Uiso 1 1 calc R . . . .
C76 C 0.7391(3) 0.34545(18) 0.32075(15) 0.0248(7) Uani 1 1 d . . . . .
C77 C 0.6702(3) 0.35467(19) 0.38007(15) 0.0266(7) Uani 1 1 d . . . . .
C85 C 0.2530(3) 0.13717(18) 0.32160(15) 0.0270(6) Uani 1 1 d D U . . .
C86 C 0.1702(3) 0.14906(19) 0.37536(15) 0.0259(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl73 C76 1.770(3) . ?
Cl74 C76 1.779(3) . ?
Cl75 C76 1.774(3) . ?
Cl80 C85 1.7710(10) . ?
Cl81 C85 1.748(4) . ?
Cl82 C85 1.783(3) . ?
Cl83 C85 1.675(8) . ?
Cl84 C85 1.790(4) . ?
O71 C77 1.245(4) . ?
O72 C77 1.229(4) . ?
O78 C86 1.246(4) . ?
O79 C86 1.216(4) . ?
N10 C9 1.395(4) . ?
N10 C11 1.404(4) . ?
N10 C14 1.416(4) . ?
N23 H23 1.0400 . ?
N23 C22 1.342(5) . ?
N23 C24 1.330(5) . ?
N35 C34 1.397(5) . ?
N35 C36 1.400(5) . ?
N35 C39 1.425(4) . ?
N48 H48 1.0400 . ?
N48 C47 1.316(5) . ?
N48 C49 1.322(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.374(6) . ?
C1 C13 1.403(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.401(5) . ?
C3 C4 1.443(5) . ?
C3 C11 1.410(4) . ?
C4 C5 1.396(5) . ?
C4 C9 1.410(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.406(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.399(5) . ?
C11 C12 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.391(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(4) . ?
C14 C19 1.398(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.395(4) . ?
C17 C18 1.401(4) . ?
C17 C20 1.477(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.393(4) . ?
C20 C25 1.395(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.368(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C26 C27 1.384(6) . ?
C26 C38 1.404(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.401(5) . ?
C28 C29 1.442(5) . ?
C28 C36 1.409(5) . ?
C29 C30 1.398(5) . ?
C29 C34 1.418(5) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(6) . ?
C31 H31 0.9300 . ?
C31 C32 1.402(5) . ?
C32 H32 0.9300 . ?
C32 C33 1.387(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.393(5) . ?
C36 C37 1.386(5) . ?
C37 H37 0.9300 . ?
C37 C38 1.392(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.382(5) . ?
C39 C44 1.380(5) . ?
C40 H40 0.9300 . ?
C40 C41 1.386(5) . ?
C41 H41 0.9300 . ?
C41 C42 1.392(5) . ?
C42 C43 1.397(5) . ?
C42 C45 1.480(4) . ?
C43 H43 0.9300 . ?
C43 C44 1.382(5) . ?
C44 H44 0.9300 . ?
C45 C46 1.383(5) . ?
C45 C50 1.404(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.410(5) . ?
C47 H47 0.9300 . ?
C49 H49 0.9300 . ?
C49 C50 1.365(5) . ?
C50 H50 0.9300 . ?
C76 C77 1.590(4) . ?
C85 C86 1.581(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N10 C11 108.7(3) . . ?
C9 N10 C14 125.5(3) . . ?
C11 N10 C14 125.7(3) . . ?
C22 N23 H23 119.3 . . ?
C24 N23 H23 119.3 . . ?
C24 N23 C22 121.4(3) . . ?
C34 N35 C36 108.9(3) . . ?
C34 N35 C39 126.5(3) . . ?
C36 N35 C39 124.2(3) . . ?
C47 N48 H48 119.0 . . ?
C47 N48 C49 121.9(3) . . ?
C49 N48 H48 119.0 . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C13 121.0(3) . . ?
C13 C1 H1 119.5 . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 132.9(3) . . ?
C2 C3 C11 119.4(3) . . ?
C11 C3 C4 107.6(3) . . ?
C5 C4 C3 134.0(3) . . ?
C5 C4 C9 119.3(3) . . ?
C9 C4 C3 106.7(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 118.0(3) . . ?
C9 C8 H8 121.0 . . ?
N10 C9 C4 108.9(3) . . ?
N10 C9 C8 129.6(3) . . ?
C8 C9 C4 121.5(3) . . ?
N10 C11 C3 108.1(3) . . ?
C12 C11 N10 130.0(3) . . ?
C12 C11 C3 121.8(3) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.7(3) . . ?
C13 C12 H12 121.1 . . ?
C1 C13 H13 119.5 . . ?
C12 C13 C1 121.1(4) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 N10 119.9(3) . . ?
C15 C14 C19 119.7(3) . . ?
C19 C14 N10 120.4(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 C20 120.9(3) . . ?
C18 C17 C20 120.4(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.9(3) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 120.1 . . ?
C18 C19 C14 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C17 122.0(3) . . ?
C21 C20 C25 118.6(3) . . ?
C25 C20 C17 119.4(3) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.0(3) . . ?
C22 C21 H21 120.5 . . ?
N23 C22 C21 120.5(3) . . ?
N23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
N23 C24 H24 119.6 . . ?
N23 C24 C25 120.9(3) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 120.2 . . ?
C24 C25 C20 119.7(3) . . ?
C24 C25 H25 120.2 . . ?
C27 C26 H26 119.7 . . ?
C27 C26 C38 120.7(4) . . ?
C38 C26 H26 119.7 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.3(3) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C29 133.9(3) . . ?
C27 C28 C36 118.8(4) . . ?
C36 C28 C29 107.3(3) . . ?
C30 C29 C28 134.0(3) . . ?
C30 C29 C34 118.9(3) . . ?
C34 C29 C28 107.0(3) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 C29 119.5(3) . . ?
C31 C30 H30 120.3 . . ?
C30 C31 H31 119.6 . . ?
C30 C31 C32 120.7(4) . . ?
C32 C31 H31 119.6 . . ?
C31 C32 H32 119.4 . . ?
C33 C32 C31 121.2(4) . . ?
C33 C32 H32 119.4 . . ?
C32 C33 H33 121.0 . . ?
C32 C33 C34 117.9(3) . . ?
C34 C33 H33 121.0 . . ?
N35 C34 C29 108.3(3) . . ?
C33 C34 N35 129.9(3) . . ?
C33 C34 C29 121.8(3) . . ?
N35 C36 C28 108.5(3) . . ?
C37 C36 N35 128.9(3) . . ?
C37 C36 C28 122.6(3) . . ?
C36 C37 H37 121.3 . . ?
C36 C37 C38 117.4(3) . . ?
C38 C37 H37 121.3 . . ?
C26 C38 H38 119.4 . . ?
C37 C38 C26 121.2(4) . . ?
C37 C38 H38 119.4 . . ?
C40 C39 N35 120.8(3) . . ?
C44 C39 N35 119.2(3) . . ?
C44 C39 C40 120.0(3) . . ?
C39 C40 H40 119.9 . . ?
C39 C40 C41 120.1(3) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 119.8 . . ?
C40 C41 C42 120.4(3) . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C43 118.6(3) . . ?
C41 C42 C45 121.2(3) . . ?
C43 C42 C45 120.1(3) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 C42 120.6(3) . . ?
C44 C43 H43 119.7 . . ?
C39 C44 C43 120.1(3) . . ?
C39 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C46 C45 C42 121.8(3) . . ?
C46 C45 C50 118.6(3) . . ?
C50 C45 C42 119.5(3) . . ?
C45 C46 H46 121.2 . . ?
C45 C46 C47 117.5(4) . . ?
C47 C46 H46 121.2 . . ?
N48 C47 C46 121.4(4) . . ?
N48 C47 H47 119.3 . . ?
C46 C47 H47 119.3 . . ?
N48 C49 H49 119.8 . . ?
N48 C49 C50 120.3(4) . . ?
C50 C49 H49 119.8 . . ?
C45 C50 H50 120.0 . . ?
C49 C50 C45 120.1(4) . . ?
C49 C50 H50 120.0 . . ?
Cl73 C76 Cl74 108.55(17) . . ?
Cl73 C76 Cl75 108.15(18) . . ?
Cl75 C76 Cl74 108.13(17) . . ?
C77 C76 Cl73 111.0(2) . . ?
C77 C76 Cl74 109.0(2) . . ?
C77 C76 Cl75 111.9(2) . . ?
O71 C77 C76 114.3(3) . . ?
O72 C77 O71 129.4(3) . . ?
O72 C77 C76 116.3(3) . . ?
Cl80 C85 Cl82 106.9(5) . . ?
Cl81 C85 Cl82 109.1(2) . . ?
Cl81 C85 Cl84 110.0(2) . . ?
Cl82 C85 Cl84 106.35(19) . . ?
Cl83 C85 Cl80 101.9(6) . . ?
Cl83 C85 Cl82 112.9(4) . . ?
C86 C85 Cl80 99.9(6) . . ?
C86 C85 Cl81 112.5(3) . . ?
C86 C85 Cl82 109.1(2) . . ?
C86 C85 Cl83 123.7(6) . . ?
C86 C85 Cl84 109.6(2) . . ?
O78 C86 C85 115.8(3) . . ?
O79 C86 O78 129.1(3) . . ?
O79 C86 C85 115.1(3) . . ?


_ins_header                      
;
TITL OHI-074_numabs in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  10.459158  18.862980  22.037062  90.0000  98.2843  90.0000
ZERR    8.00   0.000158   0.000319   0.000448   0.0000   0.0017   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O Cl
UNIT 200.00 136.00 16.00 16.00 24.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_7
_audit_block_doi                 10.5517/ccdc.csd.cc27tpwn
_database_code_depnum_ccdc_archive 'CCDC 2080282'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202103152 2021
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N2'
_chemical_formula_sum            'C23 H16 N2'
_chemical_formula_weight         320.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H16 N2'
_chemical_oxdiff_usercomment     CHCl3/DIPE
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.6497(2)
_cell_length_b                   8.90710(10)
_cell_length_c                   23.1915(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3232.74(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8253
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.2350
_cell_measurement_theta_min      3.8110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
10 -1 -2 0.1057
-10 0 2 0.1244
0 -6 -1 0.0389
0 6 1 0.0271
-1 0 15 0.0098
1 0 -15 0.0098

_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9.9949 -0.9987 -1.9887 -0.2267 -0.9613 -0.2000
-9.9944 -0.0015 1.9891 0.2223 0.8977 0.3608
0.0025 -6.0015 -0.9980 -0.0925 -0.3750 0.9654
-0.0025 6.0015 0.9980 0.0925 0.3750 -0.9654
-0.9957 0.0021 15.0023 1.0012 -0.0044 0.0250
0.9957 -0.0021 -15.0023 -1.0012 0.0044 -0.0250

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20126
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.626
_diffrn_reflns_theta_min         3.812
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  27.00   1.00    7.50    --  -42.45  57.00  60.00   91
  2  ω    -63.00  29.00   1.00    7.50    --  -42.45  37.00-150.00   92
  3  ω   -113.00 -18.00   1.00    7.50    --  -42.45 -57.00 -90.00   95
  4  ω     14.00  82.00   1.00    7.50    --   42.45 -99.00-150.00   68
  5  ω     37.00 112.00   1.00   30.00    --  111.00-111.00  90.00   75
  6  ω     85.00 178.00   1.00   30.00    --  111.00  61.00 -30.00   93
  7  ω     96.00 178.00   1.00   30.00    --  111.00  30.00  30.00   82
  8  ω     37.00 116.00   1.00   30.00    --  111.00-111.00-180.00   79
  9  ω     65.00 116.00   1.00   30.00    --  111.00-111.00 -30.00   51
 10  ω     43.00 137.00   1.00   30.00    --  111.00 -61.00-180.00   94
 11  ω     91.00 178.00   1.00   30.00    --  111.00  77.00-120.00   87
 12  ω     49.00 135.00   1.00   30.00    --  111.00 -61.00 -60.00   86
 13  ω    112.00 172.00   1.00   30.00    --  111.00  30.00 -60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0090841000
_diffrn_orient_matrix_UB_12      0.0044146000
_diffrn_orient_matrix_UB_13      0.0661353000
_diffrn_orient_matrix_UB_21      -0.0910975000
_diffrn_orient_matrix_UB_22      0.0635110000
_diffrn_orient_matrix_UB_23      -0.0063476000
_diffrn_orient_matrix_UB_31      -0.0362126000
_diffrn_orient_matrix_UB_32      -0.1607524000
_diffrn_orient_matrix_UB_33      -0.0007126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2868
_reflns_number_total             3359
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.7161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0971
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C3(H3), C8(H8), C5(H5), C24(H24), C23(H23), C11(H11),
 C21(H21), C15(H15), C6(H6), C22(H22), C2(H2), C18(H18), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N13 N 0.45240(6) 0.53555(11) 0.65237(4) 0.0267(2) Uani 1 1 d . . . . .
N1 N 0.34024(7) -0.30563(12) 0.49225(5) 0.0347(2) Uani 1 1 d . . . . .
C10 C 0.43111(7) 0.39561(13) 0.62669(5) 0.0255(2) Uani 1 1 d . . . . .
C9 C 0.42775(8) 0.38342(13) 0.56680(5) 0.0268(2) Uani 1 1 d . . . . .
H9 H 0.4381 0.4672 0.5439 0.032 Uiso 1 1 calc R . . . .
C25 C 0.40299(8) 0.61407(13) 0.69222(5) 0.0257(2) Uani 1 1 d . . . . .
C4 C 0.37353(7) -0.02694(13) 0.54674(5) 0.0264(2) Uani 1 1 d . . . . .
C7 C 0.39260(7) 0.11908(13) 0.57475(5) 0.0257(2) Uani 1 1 d . . . . .
C14 C 0.52548(8) 0.61971(13) 0.64034(5) 0.0269(2) Uani 1 1 d . . . . .
C12 C 0.39483(8) 0.13396(14) 0.63470(5) 0.0293(3) Uani 1 1 d . . . . .
H12 H 0.3832 0.0509 0.6577 0.035 Uiso 1 1 calc R . . . .
C3 C 0.39511(8) -0.05328(14) 0.48918(5) 0.0293(3) Uani 1 1 d . . . . .
H3 H 0.4213 0.0216 0.4676 0.035 Uiso 1 1 calc R . . . .
C8 C 0.40907(8) 0.24700(13) 0.54154(5) 0.0273(2) Uani 1 1 d . . . . .
H8 H 0.4074 0.2399 0.5015 0.033 Uiso 1 1 calc R . . . .
C20 C 0.44506(8) 0.74943(13) 0.70618(5) 0.0274(2) Uani 1 1 d . . . . .
C5 C 0.33381(8) -0.14512(14) 0.57592(6) 0.0306(3) Uani 1 1 d . . . . .
H5 H 0.3171 -0.1336 0.6141 0.037 Uiso 1 1 calc R . . . .
C24 C 0.32358(8) 0.57738(14) 0.71541(5) 0.0292(3) Uani 1 1 d . . . . .
H24 H 0.2953 0.4897 0.7049 0.035 Uiso 1 1 calc R . . . .
C19 C 0.52255(8) 0.75399(14) 0.67248(5) 0.0282(3) Uani 1 1 d . . . . .
C23 C 0.28833(8) 0.67679(15) 0.75488(5) 0.0334(3) Uani 1 1 d . . . . .
H23 H 0.2355 0.6550 0.7712 0.040 Uiso 1 1 calc R . . . .
C11 C 0.41406(8) 0.27030(14) 0.66059(5) 0.0300(3) Uani 1 1 d . . . . .
H11 H 0.4155 0.2779 0.7006 0.036 Uiso 1 1 calc R . . . .
C21 C 0.40815(9) 0.84678(14) 0.74652(5) 0.0322(3) Uani 1 1 d . . . . .
H21 H 0.4356 0.9354 0.7568 0.039 Uiso 1 1 calc R . . . .
C15 C 0.59463(8) 0.58406(15) 0.60496(5) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.5970 0.4937 0.5850 0.038 Uiso 1 1 calc R . . . .
C6 C 0.31956(8) -0.27957(14) 0.54745(6) 0.0334(3) Uani 1 1 d . . . . .
H6 H 0.2939 -0.3570 0.5680 0.040 Uiso 1 1 calc R . . . .
C22 C 0.33055(9) 0.80920(15) 0.77071(5) 0.0350(3) Uani 1 1 d . . . . .
H22 H 0.3059 0.8726 0.7979 0.042 Uiso 1 1 calc R . . . .
C2 C 0.37734(8) -0.19111(15) 0.46442(6) 0.0332(3) Uani 1 1 d . . . . .
H2 H 0.3921 -0.2052 0.4260 0.040 Uiso 1 1 calc R . . . .
C18 C 0.58844(9) 0.85927(15) 0.66657(5) 0.0347(3) Uani 1 1 d . . . . .
H18 H 0.5867 0.9497 0.6866 0.042 Uiso 1 1 calc R . . . .
C16 C 0.65968(8) 0.68940(17) 0.60093(5) 0.0367(3) Uani 1 1 d . . . . .
H16 H 0.7070 0.6684 0.5780 0.044 Uiso 1 1 calc R . . . .
C17 C 0.65603(9) 0.82629(16) 0.63041(6) 0.0385(3) Uani 1 1 d . . . . .
H17 H 0.6997 0.8960 0.6256 0.046 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N13 C10 1.4210(15) . ?
N13 C25 1.3933(15) . ?
N13 C14 1.3956(15) . ?
N1 C6 1.3407(18) . ?
N1 C2 1.3395(18) . ?
C10 C9 1.3943(16) . ?
C10 C11 1.3910(16) . ?
C9 H9 0.9300 . ?
C9 C8 1.3803(16) . ?
C25 C20 1.4113(17) . ?
C25 C24 1.3929(17) . ?
C4 C7 1.4841(16) . ?
C4 C3 1.3968(17) . ?
C4 C5 1.3973(17) . ?
C7 C12 1.3973(17) . ?
C7 C8 1.3992(16) . ?
C14 C19 1.4100(17) . ?
C14 C15 1.3947(17) . ?
C12 H12 0.9300 . ?
C12 C11 1.3876(17) . ?
C3 H3 0.9300 . ?
C3 C2 1.3836(18) . ?
C8 H8 0.9300 . ?
C20 C19 1.4433(18) . ?
C20 C21 1.4002(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3856(18) . ?
C24 H24 0.9300 . ?
C24 C23 1.3880(17) . ?
C19 C18 1.4006(18) . ?
C23 H23 0.9300 . ?
C23 C22 1.4009(19) . ?
C11 H11 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.3876(19) . ?
C6 H6 0.9300 . ?
C22 H22 0.9300 . ?
C2 H2 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.381(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(2) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 N13 C10 126.02(10) . . ?
C25 N13 C14 108.52(10) . . ?
C14 N13 C10 125.42(10) . . ?
C2 N1 C6 115.66(11) . . ?
C9 C10 N13 119.64(10) . . ?
C11 C10 N13 120.80(10) . . ?
C11 C10 C9 119.55(11) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 119.96(11) . . ?
C8 C9 H9 120.0 . . ?
N13 C25 C20 108.79(10) . . ?
C24 C25 N13 129.30(11) . . ?
C24 C25 C20 121.87(11) . . ?
C3 C4 C7 121.12(11) . . ?
C3 C4 C5 116.35(11) . . ?
C5 C4 C7 122.53(11) . . ?
C12 C7 C4 121.58(11) . . ?
C12 C7 C8 117.77(11) . . ?
C8 C7 C4 120.65(10) . . ?
N13 C14 C19 108.87(10) . . ?
C15 C14 N13 129.13(11) . . ?
C15 C14 C19 121.96(11) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.26(11) . . ?
C11 C12 H12 119.4 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.82(12) . . ?
C2 C3 H3 120.1 . . ?
C9 C8 C7 121.48(11) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C25 C20 C19 106.96(10) . . ?
C21 C20 C25 119.33(12) . . ?
C21 C20 C19 133.71(12) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.47(12) . . ?
C6 C5 H5 120.3 . . ?
C25 C24 H24 121.3 . . ?
C23 C24 C25 117.36(12) . . ?
C23 C24 H24 121.3 . . ?
C14 C19 C20 106.84(10) . . ?
C18 C19 C14 119.49(12) . . ?
C18 C19 C20 133.67(12) . . ?
C24 C23 H23 119.3 . . ?
C24 C23 C22 121.49(12) . . ?
C22 C23 H23 119.3 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.96(11) . . ?
C12 C11 H11 120.0 . . ?
C20 C21 H21 120.5 . . ?
C22 C21 C20 119.00(12) . . ?
C22 C21 H21 120.5 . . ?
C14 C15 H15 121.5 . . ?
C16 C15 C14 117.06(13) . . ?
C16 C15 H15 121.5 . . ?
N1 C6 C5 124.46(12) . . ?
N1 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
C23 C22 H22 119.6 . . ?
C21 C22 C23 120.87(12) . . ?
C21 C22 H22 119.6 . . ?
N1 C2 C3 124.24(12) . . ?
N1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.74(13) . . ?
C17 C18 H18 120.6 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.76(13) . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 120.88(12) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?


_ins_header                      
;
TITL OHI-075_ana in Pbca 
REM Pbca (#61, found as Pcab in ba-c setting)
CELL 1.54184  15.649742   8.907111  23.191462  90.0000  90.0000  90.0000
ZERR    7.00   0.000225   0.000117   0.000312   0.0000   0.0000   0.0000
LATT  1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SFAC C H N
UNIT 175.00 112.00 14.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.122
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# 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_L1Ha
_database_code_depnum_ccdc_archive 'CCDC 2080285'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-27 deposited with the CCDC.	2022-01-04 downloaded from the CCDC.
;
_audit_creation_date             2020-11-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
# start Validation Reply Form
_vrf_PLAT353_L1Ha                
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N23      - H23      .       1.04 Ang.  
RESPONSE: The N-H bond was set to 
1.04 Angstroms to best approximate the 
average of the neutron diffraction 
data for this bond.
;
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 N2 O, C2 F3 O2'
_chemical_formula_sum            'C32 H21 F3 N2 O3'
_chemical_formula_weight         538.51
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H20 F3 N2 O3 S1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9194(5)
_cell_length_b                   12.6370(6)
_cell_length_c                   18.3088(8)
_cell_angle_alpha                94.871(4)
_cell_angle_beta                 94.604(4)
_cell_angle_gamma                101.786(4)
_cell_volume                     2451.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5663
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      28.4800
_cell_measurement_theta_min      2.1200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 11 -21 0.0281
-3 -11 21 0.0281
1 13 14 0.0377
-1 -13 -14 0.0377
-13 12 5 0.0491
13 -12 -5 0.0431
14 0 6 0.0566
-13 -2 -8 0.0678

_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.056
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0020 10.9747 -21.0014 0.9739 -0.2554 0.1154
-3.0020 -10.9747 21.0014 -0.9739 0.2554 -0.1154
1.0038 12.9810 13.9467 -0.0606 -0.0124 0.9854
-1.0038 -12.9810 -13.9467 0.0606 0.0124 -0.9854
-12.9777 11.9820 4.9456 0.2161 0.8550 0.4753
12.9777 -11.9820 -4.9456 -0.2161 -0.8550 -0.4753
13.9811 -0.0001 6.0077 -0.2119 -0.8777 0.3913
-12.9833 -1.9971 -7.9985 0.2144 0.8061 -0.5185

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            27245
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.044
_diffrn_reflns_theta_min         1.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0053
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  88.00   1.00   75.00    --   19.23  57.00  90.00   90
  2  ω    -11.00  89.00   1.00   75.00    --   19.23  77.00-150.00  100
  3  ω    -20.00  61.00   1.00   75.00    --   19.23 -99.00 -30.00   81
  4  ω    -51.00  49.00   1.00   75.00    --   19.23 -77.00  90.00  100
  5  ω    -25.00  92.00   1.00   75.00    --   19.23  19.00  30.00  117
  6  ω     34.00  78.00   1.00   75.00    --   19.23-178.00 -60.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0016778000
_diffrn_orient_matrix_UB_12      0.0291684000
_diffrn_orient_matrix_UB_13      -0.0313704000
_diffrn_orient_matrix_UB_21      -0.0641740000
_diffrn_orient_matrix_UB_22      0.0005089000
_diffrn_orient_matrix_UB_23      0.0032540000
_diffrn_orient_matrix_UB_31      0.0180735000
_diffrn_orient_matrix_UB_32      0.0497227000
_diffrn_orient_matrix_UB_33      0.0230730000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7515
_reflns_number_total             11328
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     727
_refine_ls_number_reflns         11328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+1.9142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F139) = Uanis(F142) = Uanis(F145) = Uanis(F138) = Uanis(F141) =
Uanis(F144) = Uanis(F140) = Uanis(F143) = Uanis(F146)
3. Others
 Fixed Sof: F138(0.4) F139(0.4) F140(0.4) F141(0.35) F142(0.35) F143(0.35)
 F144(0.25) F145(0.25) F146(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), N101(H101), C102(H102), C103(H103),
 C105(H105), C106(H106), C108(H108), C109(H109), C113(H113), C114(H114),
 C115(H115), C116(H116), C119(H119), C121(H121), C122(H122), C124(H124),
 C125(H125), C129(H129), C130(H130), C131(H131), C132(H132), C133(H133)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.19933(19) 0.93694(16) 0.51809(11) 0.0194(5) Uani 1 1 d . . . . .
H1 H 0.2095 1.0013 0.4857 0.023 Uiso 1 1 calc R . . . .
C2 C 0.0840(2) 0.8863(2) 0.53147(14) 0.0214(6) Uani 1 1 d . . . . .
H2 H 0.0141 0.9093 0.5116 0.026 Uiso 1 1 calc R . . . .
C3 C 0.0676(2) 0.8015(2) 0.57380(14) 0.0206(5) Uani 1 1 d . . . . .
H3 H -0.0133 0.7674 0.5820 0.025 Uiso 1 1 calc R . . . .
C4 C 0.1708(2) 0.76551(19) 0.60497(13) 0.0168(5) Uani 1 1 d . . . . .
C5 C 0.2896(2) 0.8210(2) 0.58937(13) 0.0203(5) Uani 1 1 d . . . . .
H5 H 0.3615 0.8002 0.6087 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3011(2) 0.9051(2) 0.54620(14) 0.0213(6) Uani 1 1 d . . . . .
H6 H 0.3806 0.9405 0.5363 0.026 Uiso 1 1 calc R . . . .
C7 C 0.1561(2) 0.67449(19) 0.65082(13) 0.0161(5) Uani 1 1 d . . . . .
C8 C 0.0362(2) 0.6257(2) 0.67001(13) 0.0195(5) Uani 1 1 d . . . . .
H8 H -0.0330 0.6519 0.6524 0.023 Uiso 1 1 calc R . . . .
C9 C 0.0173(2) 0.5416(2) 0.71330(13) 0.0199(5) Uani 1 1 d . . . . .
H9 H -0.0629 0.5108 0.7246 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1216(2) 0.50381(19) 0.73979(13) 0.0172(5) Uani 1 1 d . . . . .
N11 N 0.13115(19) 0.42244(16) 0.78547(11) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.2579(2) 0.41442(19) 0.79467(13) 0.0183(5) Uani 1 1 d . . . . .
C13 C 0.3162(2) 0.3508(2) 0.83897(14) 0.0221(6) Uani 1 1 d . . . . .
H13 H 0.2701 0.3029 0.8676 0.027 Uiso 1 1 calc R . . . .
C14 C 0.4445(2) 0.3612(2) 0.83898(15) 0.0262(6) Uani 1 1 d . . . . .
H14 H 0.4850 0.3187 0.8675 0.031 Uiso 1 1 calc R . . . .
C15 C 0.5149(3) 0.4339(2) 0.79723(15) 0.0276(6) Uani 1 1 d . . . . .
H15 H 0.6010 0.4382 0.7977 0.033 Uiso 1 1 calc R . . . .
C16 C 0.4579(2) 0.4996(2) 0.75519(15) 0.0244(6) Uani 1 1 d . . . . .
H16 H 0.5053 0.5493 0.7283 0.029 Uiso 1 1 calc R . . . .
C17 C 0.3286(2) 0.4900(2) 0.75374(13) 0.0186(5) Uani 1 1 d . . . . .
C18 C 0.2420(2) 0.54788(19) 0.71976(13) 0.0165(5) Uani 1 1 d . . . . .
C19 C 0.2580(2) 0.63296(19) 0.67590(13) 0.0171(5) Uani 1 1 d . . . . .
H19 H 0.3377 0.6624 0.6632 0.021 Uiso 1 1 calc R . . . .
C20 C 0.0316(2) 0.3618(2) 0.81965(13) 0.0174(5) Uani 1 1 d . . . . .
C21 C -0.0602(2) 0.4117(2) 0.84736(13) 0.0183(5) Uani 1 1 d . . . . .
H21 H -0.0558 0.4853 0.8439 0.022 Uiso 1 1 calc R . . . .
C22 C -0.1574(2) 0.3521(2) 0.87986(12) 0.0183(5) Uani 1 1 d . . . . .
H22 H -0.2205 0.3851 0.8959 0.022 Uiso 1 1 calc R . . . .
C23 C -0.1623(2) 0.2430(2) 0.88897(13) 0.0184(5) Uani 1 1 d . . . . .
C24 C -0.0705(2) 0.1938(2) 0.86133(13) 0.0188(5) Uani 1 1 d . . . . .
H24 H -0.0730 0.1209 0.8667 0.023 Uiso 1 1 calc R . . . .
C25 C 0.0246(2) 0.25200(19) 0.82588(13) 0.0181(5) Uani 1 1 d . . . . .
H25 H 0.0839 0.2175 0.8062 0.022 Uiso 1 1 calc R . . . .
C26 C -0.2679(2) 0.1822(2) 0.92575(13) 0.0194(5) Uani 1 1 d . . . . .
O27 O -0.37108(17) 0.20581(15) 0.91961(10) 0.0277(4) Uani 1 1 d . . . . .
C28 C -0.2461(2) 0.0936(2) 0.97075(13) 0.0191(5) Uani 1 1 d . . . . .
C29 C -0.3462(3) 0.0082(2) 0.97728(14) 0.0249(6) Uani 1 1 d . . . . .
H29 H -0.4241 0.0052 0.9516 0.030 Uiso 1 1 calc R . . . .
C30 C -0.3309(3) -0.0722(2) 1.02161(16) 0.0327(7) Uani 1 1 d . . . . .
H30 H -0.3980 -0.1295 1.0253 0.039 Uiso 1 1 calc R . . . .
C31 C -0.2164(3) -0.0673(2) 1.06026(15) 0.0308(7) Uani 1 1 d . . . . .
H31 H -0.2064 -0.1215 1.0902 0.037 Uiso 1 1 calc R . . . .
C32 C -0.1158(3) 0.0173(2) 1.05515(14) 0.0255(6) Uani 1 1 d . . . . .
H32 H -0.0389 0.0204 1.0819 0.031 Uiso 1 1 calc R . . . .
C33 C -0.1304(2) 0.0977(2) 1.00977(13) 0.0204(5) Uani 1 1 d . . . . .
H33 H -0.0627 0.1542 1.0056 0.025 Uiso 1 1 calc R . . . .
O34 O 0.21350(17) 1.10617(14) 0.44168(10) 0.0259(4) Uani 1 1 d . . . . .
C35 C 0.3109(2) 1.1239(2) 0.40912(14) 0.0203(5) Uani 1 1 d . . . . .
O36 O 0.41140(18) 1.0989(2) 0.42354(12) 0.0448(6) Uani 1 1 d . . . . .
C37 C 0.2999(2) 1.1834(2) 0.33925(15) 0.0246(6) Uani 1 1 d . . . . .
F38 F 0.27135(15) 1.11082(13) 0.27888(8) 0.0326(4) Uani 1 1 d . . . . .
F39 F 0.21133(15) 1.24166(13) 0.33841(9) 0.0334(4) Uani 1 1 d . . . . .
F40 F 0.40791(15) 1.25071(13) 0.32949(9) 0.0379(4) Uani 1 1 d . . . . .
N101 N 0.29734(19) -0.44863(16) 0.96467(11) 0.0190(5) Uani 1 1 d . . . . .
H101 H 0.2880 -0.5142 0.9960 0.023 Uiso 1 1 calc R . . . .
C102 C 0.1956(2) -0.4120(2) 0.94181(13) 0.0189(5) Uani 1 1 d . . . . .
H102 H 0.1173 -0.4447 0.9548 0.023 Uiso 1 1 calc R . . . .
C103 C 0.2056(2) -0.32678(19) 0.89940(13) 0.0177(5) Uani 1 1 d . . . . .
H103 H 0.1339 -0.3025 0.8840 0.021 Uiso 1 1 calc R . . . .
C104 C 0.3226(2) -0.27591(19) 0.87908(12) 0.0161(5) Uani 1 1 d . . . . .
C105 C 0.4260(2) -0.3164(2) 0.90561(14) 0.0206(5) Uani 1 1 d . . . . .
H105 H 0.5061 -0.2848 0.8945 0.025 Uiso 1 1 calc R . . . .
C106 C 0.4111(2) -0.4012(2) 0.94730(14) 0.0217(6) Uani 1 1 d . . . . .
H106 H 0.4811 -0.4268 0.9641 0.026 Uiso 1 1 calc R . . . .
C107 C 0.3370(2) -0.18443(19) 0.83336(13) 0.0169(5) Uani 1 1 d . . . . .
C108 C 0.4569(2) -0.1353(2) 0.81489(14) 0.0216(6) Uani 1 1 d . . . . .
H108 H 0.5256 -0.1638 0.8304 0.026 Uiso 1 1 calc R . . . .
C109 C 0.4765(2) -0.0473(2) 0.77493(14) 0.0218(6) Uani 1 1 d . . . . .
H109 H 0.5566 -0.0165 0.7635 0.026 Uiso 1 1 calc R . . . .
C110 C 0.3736(2) -0.0056(2) 0.75216(13) 0.0186(5) Uani 1 1 d . . . . .
N111 N 0.36687(19) 0.08166(17) 0.71128(11) 0.0208(5) Uani 1 1 d . . . . .
C112 C 0.2402(2) 0.0873(2) 0.69884(13) 0.0192(5) Uani 1 1 d . . . . .
C113 C 0.1872(2) 0.1622(2) 0.66304(13) 0.0218(6) Uani 1 1 d . . . . .
H113 H 0.2370 0.2198 0.6436 0.026 Uiso 1 1 calc R . . . .
C114 C 0.0575(3) 0.1481(2) 0.65723(14) 0.0242(6) Uani 1 1 d . . . . .
H114 H 0.0197 0.1967 0.6330 0.029 Uiso 1 1 calc R . . . .
C115 C -0.0179(2) 0.0624(2) 0.68691(14) 0.0242(6) Uani 1 1 d . . . . .
H115 H -0.1049 0.0536 0.6811 0.029 Uiso 1 1 calc R . . . .
C116 C 0.0359(2) -0.0094(2) 0.72487(14) 0.0213(6) Uani 1 1 d . . . . .
H116 H -0.0142 -0.0654 0.7457 0.026 Uiso 1 1 calc R . . . .
C117 C 0.1662(2) 0.0031(2) 0.73154(13) 0.0181(5) Uani 1 1 d . . . . .
C118 C 0.2515(2) -0.05507(19) 0.76631(13) 0.0162(5) Uani 1 1 d . . . . .
C119 C 0.2345(2) -0.14403(19) 0.80717(13) 0.0170(5) Uani 1 1 d . . . . .
H119 H 0.1540 -0.1766 0.8170 0.020 Uiso 1 1 calc R . . . .
C120 C 0.4697(2) 0.1470(2) 0.68250(13) 0.0191(5) Uani 1 1 d . . . . .
C121 C 0.5833(2) 0.1845(2) 0.72532(14) 0.0220(6) Uani 1 1 d . . . . .
H121 H 0.5918 0.1691 0.7740 0.026 Uiso 1 1 calc R . . . .
C122 C 0.6840(2) 0.2448(2) 0.69543(14) 0.0223(6) Uani 1 1 d . . . . .
H122 H 0.7619 0.2654 0.7230 0.027 Uiso 1 1 calc R . . . .
C123 C 0.6695(2) 0.27482(19) 0.62432(14) 0.0196(5) Uani 1 1 d . . . . .
C124 C 0.5542(2) 0.23917(19) 0.58249(14) 0.0197(5) Uani 1 1 d . . . . .
H124 H 0.5434 0.2600 0.5353 0.024 Uiso 1 1 calc R . . . .
C125 C 0.4557(2) 0.17339(19) 0.61004(13) 0.0200(5) Uani 1 1 d . . . . .
H125 H 0.3803 0.1467 0.5807 0.024 Uiso 1 1 calc R . . . .
C126 C 0.7774(2) 0.3432(2) 0.59415(13) 0.0204(5) Uani 1 1 d . . . . .
O127 O 0.88233(18) 0.32361(15) 0.60211(11) 0.0325(5) Uani 1 1 d . . . . .
C128 C 0.7549(2) 0.4372(2) 0.55485(13) 0.0204(5) Uani 1 1 d . . . . .
C129 C 0.6567(3) 0.4882(2) 0.56850(15) 0.0258(6) Uani 1 1 d . . . . .
H129 H 0.5998 0.4614 0.6011 0.031 Uiso 1 1 calc R . . . .
C130 C 0.6432(3) 0.5789(2) 0.53364(16) 0.0317(7) Uani 1 1 d . . . . .
H130 H 0.5775 0.6131 0.5429 0.038 Uiso 1 1 calc R . . . .
C131 C 0.7278(3) 0.6183(2) 0.48505(16) 0.0341(7) Uani 1 1 d . . . . .
H131 H 0.7186 0.6792 0.4617 0.041 Uiso 1 1 calc R . . . .
C132 C 0.8257(3) 0.5681(2) 0.47080(15) 0.0293(7) Uani 1 1 d . . . . .
H132 H 0.8821 0.5947 0.4379 0.035 Uiso 1 1 calc R . . . .
C133 C 0.8389(2) 0.4781(2) 0.50588(13) 0.0238(6) Uani 1 1 d . . . . .
H133 H 0.9050 0.4444 0.4966 0.029 Uiso 1 1 calc R . . . .
O134 O 0.29234(17) -0.61072(15) 1.04725(10) 0.0310(5) Uani 1 1 d . . . . .
C135 C 0.1866(2) -0.6442(2) 1.06829(14) 0.0202(5) Uani 1 1 d . . . . .
O136 O 0.08362(17) -0.62852(16) 1.04629(11) 0.0316(5) Uani 1 1 d . . . . .
C137 C 0.1896(2) -0.7123(2) 1.13410(15) 0.0261(6) Uani 1 1 d . . . . .
F138 F 0.2790(4) -0.7635(4) 1.1423(3) 0.0326(5) Uani 0.4 1 d . . P A 1
F139 F 0.2125(4) -0.6346(4) 1.1983(3) 0.0326(5) Uani 0.4 1 d . . P A 1
F140 F 0.0824(7) -0.7761(5) 1.1416(4) 0.0326(5) Uani 0.4 1 d . . P A 1
F141 F 0.2475(6) -0.7983(4) 1.1175(3) 0.0326(5) Uani 0.35 1 d . . P A 2
F142 F 0.2589(5) -0.6562(5) 1.1929(3) 0.0326(5) Uani 0.35 1 d . . P A 2
F143 F 0.0745(9) -0.7558(6) 1.1553(4) 0.0326(5) Uani 0.35 1 d . . P A 2
F144 F 0.1844(7) -0.8225(6) 1.1043(4) 0.0326(5) Uani 0.25 1 d . . P A 3
F145 F 0.2952(6) -0.6951(7) 1.1773(4) 0.0326(5) Uani 0.25 1 d . . P A 3
F146 F 0.0935(8) -0.7212(6) 1.1721(5) 0.0326(5) Uani 0.25 1 d . . P A 3


_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 H1 1.0400 . ?
N1 C2 1.342(3) . ?
N1 C6 1.337(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(3) . ?
C4 C5 1.406(3) . ?
C4 C7 1.471(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.414(3) . ?
C7 C19 1.386(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 N11 1.394(3) . ?
C10 C18 1.409(3) . ?
N11 C12 1.406(3) . ?
N11 C20 1.418(3) . ?
C12 C13 1.395(3) . ?
C12 C17 1.408(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C17 C18 1.442(3) . ?
C18 C19 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.394(3) . ?
C20 C25 1.389(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.393(3) . ?
C23 C24 1.389(3) . ?
C23 C26 1.491(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.385(3) . ?
C25 H25 0.9300 . ?
C26 O27 1.222(3) . ?
C26 C28 1.491(3) . ?
C28 C29 1.391(3) . ?
C28 C33 1.390(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.380(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.382(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.392(3) . ?
C33 H33 0.9300 . ?
O34 C35 1.251(3) . ?
C35 O36 1.217(3) . ?
C35 C37 1.547(3) . ?
C37 F38 1.348(3) . ?
C37 F39 1.329(3) . ?
C37 F40 1.341(3) . ?
N101 H101 1.0400 . ?
N101 C102 1.338(3) . ?
N101 C106 1.340(3) . ?
C102 H102 0.9300 . ?
C102 C103 1.372(3) . ?
C103 H103 0.9300 . ?
C103 C104 1.401(3) . ?
C104 C105 1.402(3) . ?
C104 C107 1.474(3) . ?
C105 H105 0.9300 . ?
C105 C106 1.358(3) . ?
C106 H106 0.9300 . ?
C107 C108 1.410(3) . ?
C107 C119 1.390(3) . ?
C108 H108 0.9300 . ?
C108 C109 1.373(3) . ?
C109 H109 0.9300 . ?
C109 C110 1.385(3) . ?
C110 N111 1.395(3) . ?
C110 C118 1.406(3) . ?
N111 C112 1.401(3) . ?
N111 C120 1.417(3) . ?
C112 C113 1.388(3) . ?
C112 C117 1.407(3) . ?
C113 H113 0.9300 . ?
C113 C114 1.385(4) . ?
C114 H114 0.9300 . ?
C114 C115 1.397(4) . ?
C115 H115 0.9300 . ?
C115 C116 1.382(3) . ?
C116 H116 0.9300 . ?
C116 C117 1.394(3) . ?
C117 C118 1.441(3) . ?
C118 C119 1.392(3) . ?
C119 H119 0.9300 . ?
C120 C121 1.385(3) . ?
C120 C125 1.399(3) . ?
C121 H121 0.9300 . ?
C121 C122 1.384(3) . ?
C122 H122 0.9300 . ?
C122 C123 1.393(3) . ?
C123 C124 1.389(3) . ?
C123 C126 1.486(3) . ?
C124 H124 0.9300 . ?
C124 C125 1.377(3) . ?
C125 H125 0.9300 . ?
C126 O127 1.221(3) . ?
C126 C128 1.492(3) . ?
C128 C129 1.387(4) . ?
C128 C133 1.389(3) . ?
C129 H129 0.9300 . ?
C129 C130 1.386(4) . ?
C130 H130 0.9300 . ?
C130 C131 1.383(4) . ?
C131 H131 0.9300 . ?
C131 C132 1.381(4) . ?
C132 H132 0.9300 . ?
C132 C133 1.380(4) . ?
C133 H133 0.9300 . ?
O134 C135 1.249(3) . ?
C135 O136 1.224(3) . ?
C135 C137 1.541(4) . ?
C137 F138 1.283(5) . ?
C137 F139 1.438(6) . ?
C137 F140 1.303(8) . ?
C137 F141 1.389(7) . ?
C137 F142 1.324(6) . ?
C137 F143 1.365(9) . ?
C137 F144 1.440(8) . ?
C137 F145 1.313(7) . ?
C137 F146 1.295(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1 119.8 . . ?
C6 N1 H1 119.8 . . ?
C6 N1 C2 120.4(2) . . ?
N1 C2 H2 119.4 . . ?
N1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 116.0(2) . . ?
C3 C4 C7 122.0(2) . . ?
C5 C4 C7 122.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
N1 C6 C5 120.7(2) . . ?
N1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C4 120.6(2) . . ?
C19 C7 C4 121.6(2) . . ?
C19 C7 C8 117.8(2) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.0(2) . . ?
C9 C8 H8 118.5 . . ?
C8 C9 H9 121.0 . . ?
C8 C9 C10 118.0(2) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 N11 130.5(2) . . ?
C9 C10 C18 120.6(2) . . ?
N11 C10 C18 108.9(2) . . ?
C10 N11 C12 108.11(19) . . ?
C10 N11 C20 126.0(2) . . ?
C12 N11 C20 125.8(2) . . ?
N11 C12 C17 109.0(2) . . ?
C13 C12 N11 130.0(2) . . ?
C13 C12 C17 120.9(2) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 C12 117.9(2) . . ?
C14 C13 H13 121.1 . . ?
C13 C14 H14 119.2 . . ?
C13 C14 C15 121.6(2) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.8(2) . . ?
C17 C16 H16 120.6 . . ?
C12 C17 C18 106.7(2) . . ?
C16 C17 C12 120.0(2) . . ?
C16 C17 C18 133.2(2) . . ?
C10 C18 C17 107.3(2) . . ?
C19 C18 C10 119.9(2) . . ?
C19 C18 C17 132.7(2) . . ?
C7 C19 C18 120.6(2) . . ?
C7 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 N11 120.4(2) . . ?
C25 C20 N11 120.3(2) . . ?
C25 C20 C21 119.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.1(2) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C26 119.0(2) . . ?
C24 C23 C22 118.6(2) . . ?
C24 C23 C26 122.3(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 119.9 . . ?
C24 C25 C20 120.1(2) . . ?
C24 C25 H25 119.9 . . ?
C23 C26 C28 119.5(2) . . ?
O27 C26 C23 120.1(2) . . ?
O27 C26 C28 120.4(2) . . ?
C29 C28 C26 119.0(2) . . ?
C33 C28 C26 121.6(2) . . ?
C33 C28 C29 119.3(2) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C29 C30 H30 120.1 . . ?
C31 C30 C29 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C30 C31 H31 119.7 . . ?
C30 C31 C32 120.7(3) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.2 . . ?
C31 C32 C33 119.7(3) . . ?
C33 C32 H32 120.2 . . ?
C28 C33 C32 120.0(2) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
O34 C35 C37 114.8(2) . . ?
O36 C35 O34 129.4(2) . . ?
O36 C35 C37 115.8(2) . . ?
F38 C37 C35 110.1(2) . . ?
F39 C37 C35 114.1(2) . . ?
F39 C37 F38 106.5(2) . . ?
F39 C37 F40 107.0(2) . . ?
F40 C37 C35 112.4(2) . . ?
F40 C37 F38 106.3(2) . . ?
C102 N101 H101 119.9 . . ?
C102 N101 C106 120.2(2) . . ?
C106 N101 H101 119.9 . . ?
N101 C102 H102 119.6 . . ?
N101 C102 C103 120.8(2) . . ?
C103 C102 H102 119.6 . . ?
C102 C103 H103 119.6 . . ?
C102 C103 C104 120.8(2) . . ?
C104 C103 H103 119.6 . . ?
C103 C104 C105 115.9(2) . . ?
C103 C104 C107 122.4(2) . . ?
C105 C104 C107 121.7(2) . . ?
C104 C105 H105 119.5 . . ?
C106 C105 C104 121.0(2) . . ?
C106 C105 H105 119.5 . . ?
N101 C106 C105 121.2(2) . . ?
N101 C106 H106 119.4 . . ?
C105 C106 H106 119.4 . . ?
C108 C107 C104 120.2(2) . . ?
C119 C107 C104 121.7(2) . . ?
C119 C107 C108 118.1(2) . . ?
C107 C108 H108 118.6 . . ?
C109 C108 C107 122.7(2) . . ?
C109 C108 H108 118.6 . . ?
C108 C109 H109 120.9 . . ?
C108 C109 C110 118.1(2) . . ?
C110 C109 H109 120.9 . . ?
C109 C110 N111 129.9(2) . . ?
C109 C110 C118 121.1(2) . . ?
N111 C110 C118 109.0(2) . . ?
C110 N111 C112 108.0(2) . . ?
C110 N111 C120 125.5(2) . . ?
C112 N111 C120 126.3(2) . . ?
N111 C112 C117 109.0(2) . . ?
C113 C112 N111 129.3(2) . . ?
C113 C112 C117 121.6(2) . . ?
C112 C113 H113 121.2 . . ?
C114 C113 C112 117.6(2) . . ?
C114 C113 H113 121.2 . . ?
C113 C114 H114 119.3 . . ?
C113 C114 C115 121.5(2) . . ?
C115 C114 H114 119.3 . . ?
C114 C115 H115 119.7 . . ?
C116 C115 C114 120.5(2) . . ?
C116 C115 H115 119.7 . . ?
C115 C116 H116 120.5 . . ?
C115 C116 C117 119.1(2) . . ?
C117 C116 H116 120.5 . . ?
C112 C117 C118 106.7(2) . . ?
C116 C117 C112 119.6(2) . . ?
C116 C117 C118 133.7(2) . . ?
C110 C118 C117 107.2(2) . . ?
C119 C118 C110 119.5(2) . . ?
C119 C118 C117 133.3(2) . . ?
C107 C119 C118 120.4(2) . . ?
C107 C119 H119 119.8 . . ?
C118 C119 H119 119.8 . . ?
C121 C120 N111 120.6(2) . . ?
C121 C120 C125 120.0(2) . . ?
C125 C120 N111 119.4(2) . . ?
C120 C121 H121 120.1 . . ?
C122 C121 C120 119.8(2) . . ?
C122 C121 H121 120.1 . . ?
C121 C122 H122 119.8 . . ?
C121 C122 C123 120.5(2) . . ?
C123 C122 H122 119.8 . . ?
C122 C123 C126 119.7(2) . . ?
C124 C123 C122 119.1(2) . . ?
C124 C123 C126 121.1(2) . . ?
C123 C124 H124 119.6 . . ?
C125 C124 C123 120.8(2) . . ?
C125 C124 H124 119.6 . . ?
C120 C125 H125 120.2 . . ?
C124 C125 C120 119.6(2) . . ?
C124 C125 H125 120.2 . . ?
C123 C126 C128 118.5(2) . . ?
O127 C126 C123 120.7(2) . . ?
O127 C126 C128 120.8(2) . . ?
C129 C128 C126 122.0(2) . . ?
C129 C128 C133 119.2(2) . . ?
C133 C128 C126 118.7(2) . . ?
C128 C129 H129 119.9 . . ?
C130 C129 C128 120.1(3) . . ?
C130 C129 H129 119.9 . . ?
C129 C130 H130 120.1 . . ?
C131 C130 C129 119.8(3) . . ?
C131 C130 H130 120.1 . . ?
C130 C131 H131 119.7 . . ?
C132 C131 C130 120.6(3) . . ?
C132 C131 H131 119.7 . . ?
C131 C132 H132 120.4 . . ?
C133 C132 C131 119.3(3) . . ?
C133 C132 H132 120.4 . . ?
C128 C133 H133 119.5 . . ?
C132 C133 C128 120.9(3) . . ?
C132 C133 H133 119.5 . . ?
O134 C135 C137 113.7(2) . . ?
O136 C135 O134 130.2(2) . . ?
O136 C135 C137 116.1(2) . . ?
F138 C137 C135 118.0(3) . . ?
F138 C137 F139 103.2(3) . . ?
F138 C137 F140 110.1(4) . . ?
F139 C137 C135 105.1(3) . . ?
F140 C137 C135 114.3(4) . . ?
F140 C137 F139 104.5(4) . . ?
F141 C137 C135 110.1(3) . . ?
F142 C137 C135 112.2(3) . . ?
F142 C137 F141 104.5(4) . . ?
F142 C137 F143 107.5(4) . . ?
F143 C137 C135 115.0(4) . . ?
F143 C137 F141 106.9(4) . . ?
F144 C137 C135 107.0(3) . . ?
F145 C137 C135 117.2(3) . . ?
F145 C137 F144 99.5(5) . . ?
F146 C137 C135 116.1(4) . . ?
F146 C137 F144 103.3(5) . . ?
F146 C137 F145 111.2(5) . . ?


_ins_header                      
;
TITL ET-BpCzPy_2_181221_scale in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073  10.919382  12.637026  18.308806  94.8707  94.6042 101.7856
ZERR    3.00   0.000491   0.000611   0.000757   0.0036   0.0035   0.0039
LATT  1
SFAC C H N O F S
UNIT 96.00 60.00 6.00 9.00 9.00 3.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.891
