# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2000976'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-07-10 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        1
_chemical_name_common            Isoquinoline+Trifluoroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H8 N, C2 F3 O2'
_chemical_formula_sum            'C11 H8 F3 N O2'
_chemical_formula_weight         243.18

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.7905(3)
_cell_length_b                   10.1855(7)
_cell_length_c                   11.2559(9)
_cell_angle_alpha                78.8360(10)
_cell_angle_beta                 80.287(2)
_cell_angle_gamma                80.584(2)
_cell_volume                     526.21(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1744
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.878

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6256
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4832
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         26.240
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2095
_reflns_number_gt                1219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.6253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2095
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0721
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.8122(6) 0.4261(3) 0.1880(3) 0.0344(7) Uani 1 1 d . . . . .
H2N H 0.637033 0.497115 0.167769 0.041 Uiso 1 1 calc R U . . .
C1 C 0.8962(7) 0.4120(3) 0.2961(3) 0.0320(8) Uani 1 1 d . . . . .
H1 H 0.796384 0.467018 0.353103 0.038 Uiso 1 1 calc R U . . .
C3 C 0.9472(7) 0.3508(4) 0.1019(3) 0.0350(8) Uani 1 1 d . . . . .
H3 H 0.881097 0.363620 0.024931 0.042 Uiso 1 1 calc R U . . .
C4 C 1.1756(7) 0.2578(4) 0.1264(3) 0.0340(8) Uani 1 1 d . . . . .
H4 H 1.270001 0.205912 0.066041 0.041 Uiso 1 1 calc R U . . .
C4A C 1.2749(7) 0.2372(3) 0.2403(3) 0.0305(8) Uani 1 1 d . . . . .
C5 C 1.5095(6) 0.1396(3) 0.2726(3) 0.0342(8) Uani 1 1 d . . . . .
H5 H 1.607491 0.083162 0.216508 0.041 Uiso 1 1 calc R U . . .
C6 C 1.5930(7) 0.1275(4) 0.3837(3) 0.0384(9) Uani 1 1 d . . . . .
H6 H 1.752652 0.063144 0.403783 0.046 Uiso 1 1 calc R U . . .
C7 C 1.4504(7) 0.2073(4) 0.4705(3) 0.0400(9) Uani 1 1 d . . . . .
H7 H 1.514009 0.196363 0.547813 0.048 Uiso 1 1 calc R U . . .
C8 C 1.2212(7) 0.3002(4) 0.4435(3) 0.0378(9) Uani 1 1 d . . . . .
H8 H 1.123039 0.353457 0.502214 0.045 Uiso 1 1 calc R U . . .
C8A C 1.1305(6) 0.3171(3) 0.3283(3) 0.0299(8) Uani 1 1 d . . . . .
F1 F -0.1221(5) 0.8076(3) 0.1673(3) 0.1016(12) Uani 1 1 d . . . . .
F2 F 0.2523(6) 0.8910(3) 0.0876(3) 0.0955(11) Uani 1 1 d . . . . .
F3 F 0.1000(6) 0.8947(3) 0.2718(3) 0.0823(9) Uani 1 1 d . . . . .
O1 O 0.3870(5) 0.6173(2) 0.1318(2) 0.0412(7) Uani 1 1 d . . . . .
O2 O 0.3494(6) 0.6433(3) 0.3273(2) 0.0526(8) Uani 1 1 d . . . . .
C9 C 0.3087(7) 0.6784(4) 0.2213(3) 0.0357(9) Uani 1 1 d . . . . .
C10 C 0.1331(7) 0.8176(4) 0.1873(4) 0.0416(9) 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
N2 C1 1.319(4) . ?
N2 C3 1.364(4) . ?
N2 H2N 1.0400 . ?
C1 C8A 1.405(4) . ?
C1 H1 0.9500 . ?
C3 C4 1.354(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.409(5) . ?
C4 H4 0.9500 . ?
C4A C5 1.419(4) . ?
C4A C8A 1.420(4) . ?
C5 C6 1.354(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.408(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.362(5) . ?
C7 H7 0.9500 . ?
C8 C8A 1.407(5) . ?
C8 H8 0.9500 . ?
F1 C10 1.303(4) . ?
F2 C10 1.320(4) . ?
F3 C10 1.321(4) . ?
O1 C9 1.258(4) . ?
O2 C9 1.217(4) . ?
C9 C10 1.540(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C3 122.3(3) . . ?
C1 N2 H2N 118.8 . . ?
C3 N2 H2N 118.8 . . ?
N2 C1 C8A 121.1(3) . . ?
N2 C1 H1 119.4 . . ?
C8A C1 H1 119.4 . . ?
C4 C3 N2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
N2 C3 H3 120.1 . . ?
C3 C4 C4A 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C4 C4A C5 123.5(3) . . ?
C4 C4A C8A 118.3(3) . . ?
C5 C4A C8A 118.2(3) . . ?
C6 C5 C4A 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C4A C5 H5 120.2 . . ?
C5 C6 C7 122.0(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C8A 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C1 C8A C8 121.8(3) . . ?
C1 C8A C4A 117.7(3) . . ?
C8 C8A C4A 120.5(3) . . ?
O2 C9 O1 129.8(3) . . ?
O2 C9 C10 117.4(3) . . ?
O1 C9 C10 112.8(3) . . ?
F1 C10 F2 106.3(4) . . ?
F1 C10 F3 106.8(3) . . ?
F2 C10 F3 104.2(3) . . ?
F1 C10 C9 112.1(3) . . ?
F2 C10 C9 113.1(3) . . ?
F3 C10 C9 113.6(3) . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2000978'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        3
_chemical_name_common            Isoquinoline+Benzenesulfonate
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 O3 S, C9 H8 N [+ C H2 Cl2]'
_chemical_formula_sum            'C15 H13 N O3 S'
_chemical_formula_weight         287.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.8573(9)
_cell_length_b                   11.8280(15)
_cell_length_c                   16.5782(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.242(3)
_cell_angle_gamma                90
_cell_volume                     1531.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    3433
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8792
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.013
_diffrn_reflns_theta_max         25.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2720
_reflns_number_gt                2127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+4.6107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2720
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2104
_refine_ls_wR_factor_gt          0.1976
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.5934(6) 0.7293(4) 0.5494(3) 0.0547(11) Uani 1 1 d . . . . .
H2N H 0.553601 0.659878 0.581030 0.066 Uiso 1 1 calc R U . . .
C1 C 0.6364(6) 0.8241(4) 0.5894(3) 0.0433(11) Uani 1 1 d . . . . .
H1 H 0.627695 0.828443 0.646020 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6003(6) 0.7209(4) 0.4673(3) 0.0486(12) Uani 1 1 d . . . . .
H3 H 0.563778 0.653017 0.440023 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6568(6) 0.8056(4) 0.4254(3) 0.0486(12) Uani 1 1 d . . . . .
H4 H 0.663132 0.797295 0.368786 0.058 Uiso 1 1 calc R U . . .
C4A C 0.7073(5) 0.9076(4) 0.4641(3) 0.0385(10) Uani 1 1 d . . . . .
C5 C 0.7687(6) 1.0005(4) 0.4222(3) 0.0502(12) Uani 1 1 d . . . . .
H5 H 0.779855 0.994332 0.365880 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8116(7) 1.0980(5) 0.4617(3) 0.0573(14) Uani 1 1 d . . . . .
H6 H 0.852887 1.159771 0.432752 0.069 Uiso 1 1 calc R U . . .
C7 C 0.7960(7) 1.1094(4) 0.5459(4) 0.0582(14) Uani 1 1 d . . . . .
H7 H 0.825785 1.178773 0.572620 0.070 Uiso 1 1 calc R U . . .
C8 C 0.7384(6) 1.0215(4) 0.5884(3) 0.0491(12) Uani 1 1 d . . . . .
H8 H 0.727655 1.029605 0.644603 0.059 Uiso 1 1 calc R U . . .
C8A C 0.6947(5) 0.9178(4) 0.5486(3) 0.0359(9) Uani 1 1 d . . . . .
S1 S 0.55669(13) 0.49745(11) 0.69397(7) 0.0427(3) Uani 1 1 d . . . . .
O1 O 0.5255(5) 0.5065(4) 0.6052(2) 0.0680(11) Uani 1 1 d . . . . .
O2 O 0.4113(4) 0.4515(4) 0.7296(3) 0.0678(11) Uani 1 1 d . . . . .
O3 O 0.6195(4) 0.6041(3) 0.7282(2) 0.0481(8) Uani 1 1 d . . . . .
C9 C 0.7247(5) 0.3976(4) 0.7143(2) 0.0342(9) Uani 1 1 d . . . . .
C10 C 0.6925(6) 0.2909(4) 0.7424(3) 0.0412(11) Uani 1 1 d . . . . .
H10 H 0.579044 0.269193 0.750312 0.049 Uiso 1 1 calc R U . . .
C11 C 0.8283(6) 0.2146(4) 0.7593(3) 0.0482(12) Uani 1 1 d . . . . .
H11 H 0.807227 0.141200 0.779228 0.058 Uiso 1 1 calc R U . . .
C12 C 0.9939(6) 0.2465(4) 0.7469(3) 0.0504(12) Uani 1 1 d . . . . .
H12 H 1.086417 0.195383 0.758948 0.060 Uiso 1 1 calc R U . . .
C13 C 1.0228(6) 0.3523(4) 0.7171(3) 0.0485(12) Uani 1 1 d . . . . .
H13 H 1.135763 0.373181 0.707789 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8903(5) 0.4294(4) 0.7003(3) 0.0412(10) Uani 1 1 d . . . . .
H14 H 0.911829 0.502390 0.679757 0.049 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C1 1.328(6) . ?
N2 C3 1.372(6) . ?
N2 H2N 1.0400 . ?
C1 C8A 1.400(6) . ?
C1 H1 0.9500 . ?
C3 C4 1.323(7) . ?
C3 H3 0.9500 . ?
C4 C4A 1.404(6) . ?
C4 H4 0.9500 . ?
C4A C5 1.413(6) . ?
C4A C8A 1.421(6) . ?
C5 C6 1.351(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.361(7) . ?
C7 H7 0.9500 . ?
C8 C8A 1.417(6) . ?
C8 H8 0.9500 . ?
S1 O2 1.448(3) . ?
S1 O3 1.448(4) . ?
S1 O1 1.470(4) . ?
S1 C9 1.776(4) . ?
C9 C10 1.379(6) . ?
C9 C14 1.397(5) . ?
C10 C11 1.402(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.373(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(7) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C3 121.4(4) . . ?
C1 N2 H2N 119.3 . . ?
C3 N2 H2N 119.3 . . ?
N2 C1 C8A 120.4(4) . . ?
N2 C1 H1 119.8 . . ?
C8A C1 H1 119.8 . . ?
C4 C3 N2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
N2 C3 H3 119.4 . . ?
C3 C4 C4A 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C4A C4 H4 119.8 . . ?
C4 C4A C5 122.6(4) . . ?
C4 C4A C8A 118.5(4) . . ?
C5 C4A C8A 118.9(4) . . ?
C6 C5 C4A 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C7 120.9(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 119.9(5) . . ?
C7 C8 H8 120.1 . . ?
C8A C8 H8 120.1 . . ?
C1 C8A C8 122.4(4) . . ?
C1 C8A C4A 118.1(4) . . ?
C8 C8A C4A 119.5(4) . . ?
O2 S1 O3 114.7(2) . . ?
O2 S1 O1 112.5(2) . . ?
O3 S1 O1 110.0(2) . . ?
O2 S1 C9 106.1(2) . . ?
O3 S1 C9 106.89(19) . . ?
O1 S1 C9 106.1(2) . . ?
C10 C9 C14 120.8(4) . . ?
C10 C9 S1 120.8(3) . . ?
C14 C9 S1 118.4(3) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.0(5) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 121.4(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 118.7(4) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.075




####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2000983'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        8
_chemical_name_common            Acridine+Dibromoacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, 2(C2 H1.50 Br2 O2)'
_chemical_formula_sum            'C17 H13 Br4 N O4'
_chemical_formula_weight         614.92

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.3247(2)
_cell_length_b                   7.9047(4)
_cell_length_c                   10.1134(5)
_cell_angle_alpha                103.479(2)
_cell_angle_beta                 96.829(3)
_cell_angle_gamma                95.388(3)
_cell_volume                     484.31(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1734
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.999

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_F_000             294
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    8.332
_shelx_estimated_absorpt_T_min   0.250
_shelx_estimated_absorpt_T_max   0.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3936
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4378
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         26.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1936
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0123P)²+1.5291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N -0.0058(7) 0.4716(6) 0.1286(4) 0.0371(9) Uani 0.5 1 d . . P A 1
H10 H -0.009671 0.448697 0.225541 0.044 Uiso 0.5 1 calc R U P A 1
C9 C -0.0058(7) 0.4716(6) 0.1286(4) 0.0371(9) Uani 0.5 1 d . . P A 2
H9 H -0.009332 0.450678 0.217155 0.044 Uiso 0.5 1 calc R U P A 2
C1 C 0.3592(9) 0.7018(7) -0.0496(6) 0.0508(13) Uani 1 1 d . . . . .
H1 H 0.366265 0.724319 -0.137320 0.061 Uiso 1 1 calc R U . . .
C2 C 0.5231(9) 0.7678(8) 0.0547(7) 0.0569(15) Uani 1 1 d . . . . .
H2 H 0.644362 0.836845 0.038997 0.068 Uiso 1 1 calc R U . . .
C3 C 0.5177(9) 0.7365(8) 0.1852(6) 0.0570(15) Uani 1 1 d . . . . .
H3 H 0.635571 0.783240 0.255940 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3457(8) 0.6401(7) 0.2115(5) 0.0449(12) Uani 1 1 d . . . . .
H4 H 0.343894 0.619313 0.300200 0.054 Uiso 1 1 calc R U . . .
C4A C 0.1687(7) 0.5703(6) 0.1066(4) 0.0348(10) Uani 1 1 d . . . . .
C9A C 0.1778(8) 0.5992(6) -0.0267(5) 0.0362(10) Uani 1 1 d . . . . .
Br1 Br 0.07881(9) 0.04949(7) 0.18430(5) 0.04916(18) Uani 1 1 d . . . . .
Br2 Br 0.50763(8) 0.19807(8) 0.39603(5) 0.0537(2) Uani 1 1 d . . . . .
O1 O 0.0597(8) 0.3824(5) 0.4124(4) 0.0702(13) Uani 1 1 d . . . . .
H1O H -0.000807 0.452528 0.466939 0.105 Uiso 0.5 1 calc R U P . .
O2 O 0.0507(6) 0.2312(5) 0.5701(4) 0.0531(9) Uani 1 1 d . . . . .
C11 C 0.0963(8) 0.2533(6) 0.4617(5) 0.0386(10) Uani 1 1 d . . . . .
C12 C 0.2061(7) 0.1123(6) 0.3751(5) 0.0355(10) Uani 1 1 d . . . . .
H12 H 0.191478 0.005371 0.411729 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C4A 1.362(6) . ?
N10 C9A 1.382(6) 2_565 ?
N10 H10 1.0400 . ?
C9 C4A 1.362(6) . ?
C9 C9A 1.382(6) 2_565 ?
C9 H9 0.9500 . ?
C1 C2 1.357(8) . ?
C1 C9A 1.416(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.402(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9500 . ?
C4 C4A 1.419(6) . ?
C4 H4 0.9500 . ?
C4A C9A 1.426(6) . ?
Br1 C12 1.931(4) . ?
Br2 C12 1.933(5) . ?
O1 C11 1.264(6) . ?
O1 H1O 0.8400 . ?
O2 C11 1.213(6) . ?
C11 C12 1.525(6) . ?
C12 H12 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
C4A N10 C9A 122.3(4) . 2_565 ?
C4A N10 H10 118.9 . . ?
C9A N10 H10 118.9 2_565 . ?
C4A C9 C9A 122.3(4) . 2_565 ?
C4A C9 H9 118.9 . . ?
C9A C9 H9 118.9 2_565 . ?
C2 C1 C9A 119.5(5) . . ?
C2 C1 H1 120.2 . . ?
C9A C1 H1 120.2 . . ?
C1 C2 C3 121.6(5) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C4A 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C9 C4A C4 121.7(4) . . ?
N10 C4A C4 121.7(4) . . ?
C9 C4A C9A 119.3(4) . . ?
N10 C4A C9A 119.3(4) . . ?
C4 C4A C9A 118.9(4) . . ?
N10 C9A C1 122.3(4) 2_565 . ?
N10 C9A C4A 118.4(4) 2_565 . ?
C1 C9A C4A 119.3(5) . . ?
C11 O1 H1O 109.5 . . ?
O2 C11 O1 126.1(5) . . ?
O2 C11 C12 117.6(4) . . ?
O1 C11 C12 116.4(4) . . ?
C11 C12 Br1 112.0(3) . . ?
C11 C12 Br2 108.1(3) . . ?
Br1 C12 Br2 111.3(2) . . ?
C11 C12 H12 108.5 . . ?
Br1 C12 H12 108.5 . . ?
Br2 C12 H12 108.5 . . ?

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2000982'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        7
_chemical_name_common            Acridine+Dichloroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, 2(C2 H1.50 Cl2 O2)'
_chemical_formula_sum            'C17 H13 Cl4 N O4'
_chemical_formula_weight         437.08

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.0822(3)
_cell_length_b                   7.8975(4)
_cell_length_c                   9.9912(19)
_cell_angle_alpha                104.058(3)
_cell_angle_beta                 96.799(2)
_cell_angle_gamma                95.159(3)
_cell_volume                     458.75(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1530
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.999

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_F_000             222
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3384
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.096
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1624
_reflns_number_gt                1433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0026P)²+0.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1624
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.0005(5) 0.4695(4) 0.1303(3) 0.0323(6) Uani 0.5 1 d . . P A 1
H10N H 0.001409 0.445572 0.228196 0.039 Uiso 0.5 1 calc R U P A 1
C9 C 0.0005(5) 0.4695(4) 0.1303(3) 0.0323(6) Uani 0.5 1 d . . P A 2
H9 H 0.001326 0.447645 0.219724 0.039 Uiso 0.5 1 calc R U P A 2
C1 C 0.3608(6) 0.7115(4) -0.0519(4) 0.0434(9) Uani 1 1 d . . . . .
H1 H 0.363576 0.734555 -0.140748 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5331(6) 0.7804(4) 0.0536(5) 0.0496(10) Uani 1 1 d . . . . .
H2 H 0.656875 0.850892 0.037014 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5315(6) 0.7494(5) 0.1857(4) 0.0485(10) Uani 1 1 d . . . . .
H3 H 0.653570 0.800240 0.257079 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3601(6) 0.6488(4) 0.2139(4) 0.0406(8) Uani 1 1 d . . . . .
H4 H 0.362087 0.627847 0.303726 0.049 Uiso 1 1 calc R U . . .
C4A C 0.1761(5) 0.5744(4) 0.1067(3) 0.0324(7) Uani 1 1 d . . . . .
C9A C 0.1780(5) 0.6052(4) -0.0272(3) 0.0319(7) Uani 1 1 d . . . . .
Cl1 Cl 0.09575(14) 0.05894(11) 0.19153(9) 0.0430(3) Uani 1 1 d . . . . .
Cl2 Cl 0.49944(14) 0.18557(13) 0.39324(10) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.0635(6) 0.3832(3) 0.4108(3) 0.0805(12) Uani 1 1 d . . . . .
H1O H 0.000337 0.454602 0.465797 0.121 Uiso 0.5 1 calc R U P . .
O2 O 0.0431(4) 0.2294(3) 0.5671(3) 0.0436(6) Uani 1 1 d . . . . .
C11 C 0.0958(5) 0.2520(4) 0.4598(4) 0.0339(7) Uani 1 1 d . . . . .
C12 C 0.2107(5) 0.1099(4) 0.3697(3) 0.0327(7) Uani 1 1 d . . . . .
H12 H 0.191527 0.000761 0.403282 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C4A 1.370(4) . ?
N10 C9A 1.383(4) 2_565 ?
N10 H10N 1.0400 . ?
C9 C4A 1.370(4) . ?
C9 C9A 1.383(4) 2_565 ?
C9 H9 0.9500 . ?
C1 C2 1.365(5) . ?
C1 C9A 1.414(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.352(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.427(5) . ?
C4 H4 0.9500 . ?
C4A C9A 1.418(5) . ?
Cl1 C12 1.768(3) . ?
Cl2 C12 1.772(3) . ?
O1 C11 1.270(4) . ?
O1 H1O 0.8400 . ?
O2 C11 1.203(4) . ?
C11 C12 1.535(4) . ?
C12 H12 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
C4A N10 C9A 121.7(3) . 2_565 ?
C4A N10 H10N 119.2 . . ?
C9A N10 H10N 119.2 2_565 . ?
C4A C9 C9A 121.7(3) . 2_565 ?
C4A C9 H9 119.2 . . ?
C9A C9 H9 119.2 2_565 . ?
C2 C1 C9A 119.1(4) . . ?
C2 C1 H1 120.5 . . ?
C9A C1 H1 120.5 . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C4A 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C4A C4 H4 120.5 . . ?
C9 C4A C9A 119.5(3) . . ?
N10 C4A C9A 119.5(3) . . ?
C9 C4A C4 120.9(3) . . ?
N10 C4A C4 120.9(3) . . ?
C9A C4A C4 119.6(3) . . ?
N10 C9A C1 121.7(3) 2_565 . ?
N10 C9A C4A 118.8(3) 2_565 . ?
C1 C9A C4A 119.5(3) . . ?
C11 O1 H1O 109.5 . . ?
O2 C11 O1 126.3(3) . . ?
O2 C11 C12 118.4(3) . . ?
O1 C11 C12 115.3(3) . . ?
C11 C12 Cl1 112.0(2) . . ?
C11 C12 Cl2 108.1(2) . . ?
Cl1 C12 Cl2 110.83(18) . . ?
C11 C12 H12 108.6 . . ?
Cl1 C12 H12 108.6 . . ?
Cl2 C12 H12 108.6 . . ?

_refine_diff_density_max         0.284
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.052

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 2000984'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        9
_chemical_name_common            Acridine+Chloroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 H2 Cl O2'
_chemical_formula_sum            'C15 H12 Cl N O2'
_chemical_formula_weight         273.71

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2478(4)
_cell_length_b                   8.8083(3)
_cell_length_c                   11.5321(6)
_cell_angle_alpha                69.5500(10)
_cell_angle_beta                 73.313(2)
_cell_angle_gamma                67.4180(10)
_cell_volume                     626.90(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1700
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.301
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6513
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5222
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.601
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2513
_reflns_number_gt                1953
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.4739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.7124(3) 0.4409(2) 0.66074(17) 0.0209(4) Uani 1 1 d . . . . .
H10N H 0.765164 0.335136 0.733437 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3478(4) 0.8771(3) 0.6250(2) 0.0277(6) Uani 1 1 d . . . . .
H1 H 0.294268 0.975625 0.561365 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2841(4) 0.8784(3) 0.7471(2) 0.0297(6) Uani 1 1 d . . . . .
H2 H 0.187019 0.977993 0.768492 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3615(4) 0.7321(3) 0.8432(2) 0.0291(6) Uani 1 1 d . . . . .
H3 H 0.314588 0.734669 0.928576 0.035 Uiso 1 1 calc R U . . .
C4 C 0.5012(4) 0.5885(3) 0.8156(2) 0.0257(5) Uani 1 1 d . . . . .
H4 H 0.551445 0.491530 0.881217 0.031 Uiso 1 1 calc R U . . .
C4A C 0.5721(3) 0.5837(3) 0.6882(2) 0.0208(5) Uani 1 1 d . . . . .
C5 C 0.9332(4) 0.2813(3) 0.5146(2) 0.0269(5) Uani 1 1 d . . . . .
H5 H 0.980165 0.185076 0.581493 0.032 Uiso 1 1 calc R U . . .
C6 C 1.0072(4) 0.2750(3) 0.3930(3) 0.0323(6) Uani 1 1 d . . . . .
H6 H 1.107616 0.174080 0.375891 0.039 Uiso 1 1 calc R U . . .
C7 C 0.9374(4) 0.4163(3) 0.2915(2) 0.0328(6) Uani 1 1 d . . . . .
H7 H 0.991901 0.408986 0.207528 0.039 Uiso 1 1 calc R U . . .
C8 C 0.7933(4) 0.5617(3) 0.3134(2) 0.0284(6) Uani 1 1 d . . . . .
H8 H 0.746018 0.654823 0.244842 0.034 Uiso 1 1 calc R U . . .
C8A C 0.7129(4) 0.5751(3) 0.4387(2) 0.0224(5) Uani 1 1 d . . . . .
C9 C 0.5648(4) 0.7216(3) 0.4664(2) 0.0228(5) Uani 1 1 d . . . . .
H9 H 0.511690 0.816278 0.400301 0.027 Uiso 1 1 calc R U . . .
C9A C 0.4945(4) 0.7294(3) 0.5908(2) 0.0226(5) Uani 1 1 d . . . . .
C10A C 0.7851(3) 0.4331(3) 0.5405(2) 0.0213(5) Uani 1 1 d . . . . .
Cl1 Cl 0.74022(11) -0.26384(8) 0.98773(6) 0.0362(2) Uani 1 1 d . . . . .
O1 O 0.8174(3) 0.18444(19) 0.84776(15) 0.0272(4) Uani 1 1 d . . . . .
O2 O 0.6768(3) 0.0531(2) 0.77921(17) 0.0401(5) Uani 1 1 d . . . . .
C11 C 0.7519(4) 0.0621(3) 0.8570(2) 0.0252(5) Uani 1 1 d . . . . .
C12 C 0.7769(4) -0.0730(3) 0.9827(2) 0.0269(5) Uani 1 1 d . . . . .
H12A H 0.678006 -0.025379 1.050669 0.032 Uiso 1 1 calc R U . . .
H12B H 0.914853 -0.100932 0.998753 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C10A 1.350(3) . ?
N10 C4A 1.352(3) . ?
N10 H10N 1.0400 . ?
C1 C2 1.353(3) . ?
C1 C9A 1.426(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.417(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.356(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.420(3) . ?
C4 H4 0.9500 . ?
C4A C9A 1.424(3) . ?
C5 C6 1.362(3) . ?
C5 C10A 1.422(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(4) . ?
C7 H7 0.9500 . ?
C8 C8A 1.423(3) . ?
C8 H8 0.9500 . ?
C8A C9 1.395(3) . ?
C8A C10A 1.428(3) . ?
C9 C9A 1.394(3) . ?
C9 H9 0.9500 . ?
Cl1 C12 1.779(2) . ?
O1 C11 1.297(3) . ?
O2 C11 1.213(3) . ?
C11 C12 1.527(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C10A N10 C4A 121.14(19) . . ?
C10A N10 H10N 119.4 . . ?
C4A N10 H10N 119.4 . . ?
C2 C1 C9A 120.7(2) . . ?
C2 C1 H1 119.6 . . ?
C9A C1 H1 119.6 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C4A 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C4A C4 H4 120.1 . . ?
N10 C4A C4 119.7(2) . . ?
N10 C4A C9A 120.7(2) . . ?
C4 C4A C9A 119.6(2) . . ?
C6 C5 C10A 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C10A C5 H5 120.3 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C8A 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C9 C8A C8 122.5(2) . . ?
C9 C8A C10A 118.5(2) . . ?
C8 C8A C10A 119.0(2) . . ?
C9A C9 C8A 120.2(2) . . ?
C9A C9 H9 119.9 . . ?
C8A C9 H9 119.9 . . ?
C9 C9A C4A 118.7(2) . . ?
C9 C9A C1 122.9(2) . . ?
C4A C9A C1 118.3(2) . . ?
N10 C10A C5 119.8(2) . . ?
N10 C10A C8A 120.8(2) . . ?
C5 C10A C8A 119.4(2) . . ?
O2 C11 O1 126.2(2) . . ?
O2 C11 C12 122.7(2) . . ?
O1 C11 C12 111.1(2) . . ?
C11 C12 Cl1 112.93(17) . . ?
C11 C12 H12A 109.0 . . ?
Cl1 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
Cl1 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2000987'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        12
_chemical_name_common            Benzoquinoline+Benzenesulfonate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C6 H5 O3 S [+ C H2 Cl2]'
_chemical_formula_sum            'C19 H15 N O3 S'
_chemical_formula_weight         337.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.4888(2)
_cell_length_b                   12.3779(4)
_cell_length_c                   19.0995(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.448(2)
_cell_angle_gamma                90
_cell_volume                     1755.50(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    5313
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.200
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13309
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.966
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3168
_reflns_number_gt                2278
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+2.4083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6146(4) 0.2669(2) 0.49967(13) 0.0225(6) Uani 1 1 d . . . . .
H1N H 0.622698 0.250268 0.446797 0.027 Uiso 1 1 calc R U . . .
C1A C 0.6630(4) 0.3675(2) 0.52452(15) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.5576(5) 0.1887(3) 0.53953(17) 0.0270(7) Uani 1 1 d . . . . .
H2 H 0.529200 0.119456 0.519636 0.032 Uiso 1 1 calc R U . . .
C3 C 0.5395(5) 0.2079(3) 0.60986(17) 0.0296(8) Uani 1 1 d . . . . .
H3 H 0.497535 0.152920 0.638319 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5837(5) 0.3080(3) 0.63727(17) 0.0256(7) Uani 1 1 d . . . . .
H4 H 0.570708 0.322641 0.685178 0.031 Uiso 1 1 calc R U . . .
C4A C 0.6475(4) 0.3891(3) 0.59607(15) 0.0210(7) Uani 1 1 d . . . . .
C5 C 0.6952(4) 0.4941(3) 0.62382(16) 0.0255(7) Uani 1 1 d . . . . .
H5 H 0.681719 0.510363 0.671459 0.031 Uiso 1 1 calc R U . . .
C6 C 0.7589(4) 0.5699(3) 0.58318(17) 0.0265(7) Uani 1 1 d . . . . .
H6 H 0.793947 0.638262 0.603034 0.032 Uiso 1 1 calc R U . . .
C6A C 0.7749(4) 0.5494(3) 0.51029(16) 0.0245(7) Uani 1 1 d . . . . .
C7 C 0.8408(5) 0.6304(3) 0.46815(18) 0.0293(8) Uani 1 1 d . . . . .
H7 H 0.875489 0.698528 0.488448 0.035 Uiso 1 1 calc R U . . .
C8 C 0.8550(5) 0.6119(3) 0.39897(18) 0.0339(8) Uani 1 1 d . . . . .
H8 H 0.898780 0.667386 0.371317 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8056(5) 0.5120(3) 0.36803(17) 0.0320(8) Uani 1 1 d . . . . .
H9 H 0.815560 0.500121 0.319546 0.038 Uiso 1 1 calc R U . . .
C10 C 0.7429(5) 0.4311(3) 0.40745(16) 0.0268(7) Uani 1 1 d . . . . .
H10 H 0.709999 0.363323 0.386214 0.032 Uiso 1 1 calc R U . . .
C10A C 0.7271(4) 0.4482(3) 0.47990(16) 0.0218(7) Uani 1 1 d . . . . .
S1 S 0.47520(13) 0.10319(7) 0.34442(4) 0.0280(2) Uani 1 1 d . . . . .
O1 O 0.6133(3) 0.18415(19) 0.36800(11) 0.0318(6) Uani 1 1 d . . . . .
O2 O 0.5296(4) 0.0340(2) 0.28970(12) 0.0391(7) Uani 1 1 d . . . . .
O3 O 0.4154(4) 0.0456(2) 0.40317(12) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.2861(5) 0.1789(3) 0.30508(16) 0.0265(7) Uani 1 1 d . . . . .
C12 C 0.3130(5) 0.2744(3) 0.26950(16) 0.0265(7) Uani 1 1 d . . . . .
H12 H 0.431563 0.299936 0.266789 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1650(5) 0.3322(3) 0.23799(17) 0.0340(9) Uani 1 1 d . . . . .
H13 H 0.182413 0.396757 0.212868 0.041 Uiso 1 1 calc R U . . .
C14 C -0.0070(6) 0.2961(3) 0.24302(19) 0.0406(9) Uani 1 1 d . . . . .
H14 H -0.107954 0.336254 0.221876 0.049 Uiso 1 1 calc R U . . .
C15 C -0.0326(6) 0.2018(4) 0.2787(2) 0.0481(11) Uani 1 1 d . . . . .
H15 H -0.151417 0.177357 0.281958 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1137(5) 0.1421(3) 0.30995(19) 0.0395(10) Uani 1 1 d . . . . .
H16 H 0.095530 0.076913 0.334305 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.336(4) . ?
N1 C1A 1.365(4) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.412(4) . ?
C1A C10A 1.436(4) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.397(4) . ?
C4 H4 0.9500 . ?
C4A C5 1.431(4) . ?
C5 C6 1.344(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.435(4) . ?
C6 H6 0.9500 . ?
C6A C10A 1.407(5) . ?
C6A C7 1.414(5) . ?
C7 C8 1.359(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9500 . ?
C10 C10A 1.420(4) . ?
C10 H10 0.9500 . ?
S1 O3 1.449(2) . ?
S1 O2 1.450(2) . ?
S1 O1 1.468(3) . ?
S1 C11 1.781(4) . ?
C11 C16 1.383(5) . ?
C11 C12 1.392(5) . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(6) . ?
C15 H15 0.9500 . ?
C16 H16 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
C2 N1 C1A 123.6(3) . . ?
C2 N1 H1N 118.2 . . ?
C1A N1 H1N 118.2 . . ?
N1 C1A C4A 117.3(3) . . ?
N1 C1A C10A 121.5(3) . . ?
C4A C1A C10A 121.3(3) . . ?
N1 C2 C3 120.4(3) . . ?
N1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C4A 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C1A 119.1(3) . . ?
C4 C4A C5 122.1(3) . . ?
C1A C4A C5 118.8(3) . . ?
C6 C5 C4A 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C6A 121.1(3) . . ?
C5 C6 H6 119.4 . . ?
C6A C6 H6 119.4 . . ?
C10A C6A C7 119.0(3) . . ?
C10A C6A C6 120.6(3) . . ?
C7 C6A C6 120.4(3) . . ?
C8 C7 C6A 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C6A C7 H7 119.6 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C10A 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C10A C10 H10 119.9 . . ?
C6A C10A C10 119.1(3) . . ?
C6A C10A C1A 117.5(3) . . ?
C10 C10A C1A 123.4(3) . . ?
O3 S1 O2 114.28(16) . . ?
O3 S1 O1 111.99(14) . . ?
O2 S1 O1 111.84(16) . . ?
O3 S1 C11 106.09(16) . . ?
O2 S1 C11 106.82(14) . . ?
O1 S1 C11 105.07(15) . . ?
C16 C11 C12 120.6(3) . . ?
C16 C11 S1 119.7(3) . . ?
C12 C11 S1 119.7(3) . . ?
C13 C12 C11 119.4(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.7(4) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.1(4) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2000980'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        5
_chemical_name_common            Acridine+Trichloroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 Cl3 O2'
_chemical_formula_sum            'C15 H10 Cl3 N O2'
_chemical_formula_weight         342.59

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.8497(4)
_cell_length_b                   9.3744(8)
_cell_length_c                   12.0307(10)
_cell_angle_alpha                76.517(3)
_cell_angle_beta                 74.637(5)
_cell_angle_gamma                79.462(5)
_cell_volume                     718.31(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2181
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.640
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6478
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         26.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2875
_reflns_number_gt                2068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+0.5339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2875
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.2728(3) 0.3897(2) 0.48416(17) 0.0334(5) Uani 1 1 d . . . . .
H10N H 0.311006 0.336135 0.413248 0.040 Uiso 1 1 calc R U . . .
C1 C 0.1882(4) 0.7725(3) 0.5327(2) 0.0415(7) Uani 1 1 d . . . . .
H1 H 0.149975 0.825256 0.595271 0.050 Uiso 1 1 calc R U . . .
C2 C 0.2272(4) 0.8471(3) 0.4197(3) 0.0454(7) Uani 1 1 d . . . . .
H2 H 0.216027 0.952084 0.403477 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2843(4) 0.7696(4) 0.3260(2) 0.0447(7) Uani 1 1 d . . . . .
H3 H 0.312795 0.823651 0.247500 0.054 Uiso 1 1 calc R U . . .
C4 C 0.2994(4) 0.6198(3) 0.3453(2) 0.0400(7) Uani 1 1 d . . . . .
H4 H 0.336836 0.569818 0.281122 0.048 Uiso 1 1 calc R U . . .
C4A C 0.2588(3) 0.5390(3) 0.4625(2) 0.0333(6) Uani 1 1 d . . . . .
C5 C 0.2612(4) 0.1508(3) 0.6111(2) 0.0412(7) Uani 1 1 d . . . . .
H5 H 0.297612 0.102902 0.545717 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2292(4) 0.0707(4) 0.7223(3) 0.0481(7) Uani 1 1 d . . . . .
H6 H 0.245369 -0.034148 0.734070 0.058 Uiso 1 1 calc R U . . .
C7 C 0.1728(4) 0.1388(4) 0.8206(3) 0.0501(8) Uani 1 1 d . . . . .
H7 H 0.150203 0.079398 0.897357 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1502(4) 0.2882(4) 0.8073(2) 0.0454(7) Uani 1 1 d . . . . .
H8 H 0.111325 0.332681 0.874542 0.054 Uiso 1 1 calc R U . . .
C8A C 0.1846(4) 0.3788(3) 0.6923(2) 0.0348(6) Uani 1 1 d . . . . .
C9 C 0.1676(4) 0.5319(3) 0.6720(2) 0.0367(6) Uani 1 1 d . . . . .
H9 H 0.130226 0.580827 0.736788 0.044 Uiso 1 1 calc R U . . .
C9A C 0.2045(3) 0.6152(3) 0.5577(2) 0.0345(6) Uani 1 1 d . . . . .
C10A C 0.2394(3) 0.3071(3) 0.5941(2) 0.0342(6) Uani 1 1 d . . . . .
Cl1 Cl 0.25820(12) 0.43688(9) 0.04949(7) 0.0544(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17523(14) 0.13712(10) 0.14237(7) 0.0649(3) Uani 1 1 d . . . . .
Cl3 Cl 0.57444(13) 0.19569(10) 0.00593(7) 0.0641(3) Uani 1 1 d . . . . .
O1 O 0.2853(3) 0.2545(3) 0.31461(17) 0.0599(6) Uani 1 1 d . . . . .
O2 O 0.5955(3) 0.2997(3) 0.21102(19) 0.0632(6) Uani 1 1 d . . . . .
C12 C 0.3627(4) 0.2584(3) 0.1105(2) 0.0377(6) Uani 1 1 d . . . . .
C11 C 0.4245(4) 0.2715(3) 0.2240(2) 0.0396(6) 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
N10 C10A 1.352(3) . ?
N10 C4A 1.353(3) . ?
N10 H10N 1.0400 . ?
C1 C2 1.357(4) . ?
C1 C9A 1.424(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.412(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9500 . ?
C4 C4A 1.418(4) . ?
C4 H4 0.9500 . ?
C4A C9A 1.420(3) . ?
C5 C6 1.355(4) . ?
C5 C10A 1.417(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(4) . ?
C7 H7 0.9500 . ?
C8 C8A 1.429(4) . ?
C8 H8 0.9500 . ?
C8A C9 1.387(4) . ?
C8A C10A 1.425(4) . ?
C9 C9A 1.398(4) . ?
C9 H9 0.9500 . ?
Cl1 C12 1.766(3) . ?
Cl2 C12 1.778(3) . ?
Cl3 C12 1.760(3) . ?
O1 C11 1.244(3) . ?
O2 C11 1.209(3) . ?
C12 C11 1.569(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
C10A N10 C4A 122.8(2) . . ?
C10A N10 H10N 118.6 . . ?
C4A N10 H10N 118.6 . . ?
C2 C1 C9A 120.2(3) . . ?
C2 C1 H1 119.9 . . ?
C9A C1 H1 119.9 . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C4A 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C4A C4 H4 120.4 . . ?
N10 C4A C4 120.4(2) . . ?
N10 C4A C9A 119.8(2) . . ?
C4 C4A C9A 119.8(3) . . ?
C6 C5 C10A 118.9(3) . . ?
C6 C5 H5 120.6 . . ?
C10A C5 H5 120.6 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C9 C8A C10A 118.8(2) . . ?
C9 C8A C8 123.3(2) . . ?
C10A C8A C8 117.9(3) . . ?
C8A C9 C9A 121.0(2) . . ?
C8A C9 H9 119.5 . . ?
C9A C9 H9 119.5 . . ?
C9 C9A C4A 118.2(3) . . ?
C9 C9A C1 123.0(2) . . ?
C4A C9A C1 118.8(2) . . ?
N10 C10A C5 120.1(2) . . ?
N10 C10A C8A 119.4(2) . . ?
C5 C10A C8A 120.5(2) . . ?
C11 C12 Cl3 111.87(19) . . ?
C11 C12 Cl1 107.14(18) . . ?
Cl3 C12 Cl1 108.99(14) . . ?
C11 C12 Cl2 112.10(18) . . ?
Cl3 C12 Cl2 108.31(15) . . ?
Cl1 C12 Cl2 108.33(15) . . ?
O2 C11 O1 129.6(3) . . ?
O2 C11 C12 116.5(2) . . ?
O1 C11 C12 113.8(2) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.052

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 2000979'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        4
_chemical_name_common            Acridine+Trifluoroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 F3 O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.5335(3)
_cell_length_b                   18.6879(5)
_cell_length_c                   7.1523(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.999(2)
_cell_angle_gamma                90
_cell_volume                     1264.77(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2838
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8996
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         26.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2545
_reflns_number_gt                2064
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.8788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2545
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.56569(16) 0.46913(8) 0.7502(2) 0.0277(4) Uani 1 1 d . . . . .
H10N H 0.625192 0.509135 0.696467 0.033 Uiso 1 1 calc R U . . .
C1 C 0.2007(2) 0.44486(12) 0.8599(3) 0.0399(5) Uani 1 1 d . . . . .
H1 H 0.143165 0.410137 0.910717 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1448(2) 0.50909(13) 0.8040(3) 0.0419(5) Uani 1 1 d . . . . .
H2 H 0.048094 0.518738 0.813238 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2300(2) 0.56188(12) 0.7319(3) 0.0390(5) Uani 1 1 d . . . . .
H3 H 0.189363 0.606892 0.694957 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3691(2) 0.54990(11) 0.7141(3) 0.0332(4) Uani 1 1 d . . . . .
H4 H 0.425010 0.586150 0.666565 0.040 Uiso 1 1 calc R U . . .
C4A C 0.42799(19) 0.48271(10) 0.7675(2) 0.0289(4) Uani 1 1 d . . . . .
C5 C 0.7735(2) 0.39542(10) 0.7767(3) 0.0320(4) Uani 1 1 d . . . . .
H5 H 0.825526 0.431805 0.722965 0.038 Uiso 1 1 calc R U . . .
C6 C 0.8361(2) 0.33225(11) 0.8331(3) 0.0359(5) Uani 1 1 d . . . . .
H6 H 0.932639 0.324783 0.817985 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7603(2) 0.27745(11) 0.9137(3) 0.0402(5) Uani 1 1 d . . . . .
H7 H 0.807164 0.234239 0.953764 0.048 Uiso 1 1 calc R U . . .
C8 C 0.6217(2) 0.28587(11) 0.9344(3) 0.0390(5) Uani 1 1 d . . . . .
H8 H 0.571721 0.248336 0.986745 0.047 Uiso 1 1 calc R U . . .
C8A C 0.5511(2) 0.35086(10) 0.8779(3) 0.0311(4) Uani 1 1 d . . . . .
C9 C 0.4098(2) 0.36386(11) 0.8977(3) 0.0358(5) Uani 1 1 d . . . . .
H9 H 0.356243 0.327655 0.949533 0.043 Uiso 1 1 calc R U . . .
C9A C 0.3453(2) 0.42863(11) 0.8433(3) 0.0322(4) Uani 1 1 d . . . . .
C10A C 0.62925(19) 0.40596(10) 0.7997(2) 0.0285(4) Uani 1 1 d . . . . .
F1 F 0.94727(14) 0.66870(8) 0.78104(19) 0.0542(4) Uani 1 1 d . . . . .
F2 F 0.83942(16) 0.74187(8) 0.5872(3) 0.0805(6) Uani 1 1 d . . . . .
F3 F 0.94154(14) 0.65002(8) 0.4884(2) 0.0611(4) Uani 1 1 d . . . . .
O1 O 0.75151(15) 0.56440(7) 0.6644(2) 0.0406(4) Uani 1 1 d . . . . .
O2 O 0.61494(16) 0.65860(9) 0.5754(3) 0.0545(5) Uani 1 1 d . . . . .
C11 C 0.72678(19) 0.62813(10) 0.6195(3) 0.0308(4) Uani 1 1 d . . . . .
C12 C 0.8624(2) 0.67286(10) 0.6178(3) 0.0347(5) 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
N10 C10A 1.354(2) . ?
N10 C4A 1.357(2) . ?
N10 H10N 1.0400 . ?
C1 C2 1.354(3) . ?
C1 C9A 1.431(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.414(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.409(3) . ?
C4 H4 0.9500 . ?
C4A C9A 1.429(3) . ?
C5 C6 1.361(3) . ?
C5 C10A 1.419(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.357(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.423(3) . ?
C8 H8 0.9500 . ?
C8A C9 1.393(3) . ?
C8A C10A 1.425(3) . ?
C9 C9A 1.391(3) . ?
C9 H9 0.9500 . ?
F1 C12 1.340(2) . ?
F2 C12 1.322(2) . ?
F3 C12 1.334(2) . ?
O1 C11 1.248(2) . ?
O2 C11 1.216(2) . ?
C11 C12 1.541(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
C10A N10 C4A 123.09(16) . . ?
C10A N10 H10N 118.5 . . ?
C4A N10 H10N 118.5 . . ?
C2 C1 C9A 120.79(19) . . ?
C2 C1 H1 119.6 . . ?
C9A C1 H1 119.6 . . ?
C1 C2 C3 120.25(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C4A 118.67(18) . . ?
C3 C4 H4 120.7 . . ?
C4A C4 H4 120.7 . . ?
N10 C4A C4 119.97(16) . . ?
N10 C4A C9A 119.13(18) . . ?
C4 C4A C9A 120.88(17) . . ?
C6 C5 C10A 118.82(18) . . ?
C6 C5 H5 120.6 . . ?
C10A C5 H5 120.6 . . ?
C5 C6 C7 121.39(19) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 120.85(19) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C8A 120.07(18) . . ?
C7 C8 H8 120.0 . . ?
C8A C8 H8 120.0 . . ?
C9 C8A C8 123.35(18) . . ?
C9 C8A C10A 118.18(18) . . ?
C8 C8A C10A 118.46(18) . . ?
C9A C9 C8A 121.56(17) . . ?
C9A C9 H9 119.2 . . ?
C8A C9 H9 119.2 . . ?
C9 C9A C4A 118.42(17) . . ?
C9 C9A C1 123.98(18) . . ?
C4A C9A C1 117.60(19) . . ?
N10 C10A C5 119.99(16) . . ?
N10 C10A C8A 119.60(17) . . ?
C5 C10A C8A 120.40(18) . . ?
O2 C11 O1 130.21(19) . . ?
O2 C11 C12 116.99(18) . . ?
O1 C11 C12 112.79(17) . . ?
F2 C12 F3 107.09(18) . . ?
F2 C12 F1 105.71(18) . . ?
F3 C12 F1 104.67(16) . . ?
F2 C12 C11 114.12(17) . . ?
F3 C12 C11 112.24(17) . . ?
F1 C12 C11 112.32(16) . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.044

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2000977'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_date             2020-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            'isoquinolinium trichloroacatate'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 N, C2 Cl3 O2'
_chemical_formula_sum            'C11 H8 Cl3 N O2'
_chemical_formula_weight         292.53
_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      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                   10.1155(6)
_cell_length_b                   11.3509(4)
_cell_length_c                   11.1128(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.011(2)
_cell_angle_gamma                90
_cell_volume                     1191.13(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    170
_cell_measurement_theta_max      30.999
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0820 before and 0.0725 after correction. The Ratio of minimum to maximum transmission is 0.8937. 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    1.631
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.350
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             3863
_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         0.373
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0548
_refine_ls_restrained_S_all      1.047
_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)+(0.0327P)²+1.0988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1205
_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:
 N2(H2), C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
;
_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
Cl1 Cl 0.06013(7) 0.49975(5) 0.85922(7) 0.03408(17) Uani 1 1 d . . . . .
Cl2 Cl 0.21532(7) 0.68438(6) 1.02829(6) 0.03208(16) Uani 1 1 d . . . . .
Cl3 Cl 0.05409(7) 0.73292(6) 0.76049(7) 0.03269(17) Uani 1 1 d . . . . .
O1 O 0.3507(2) 0.69169(15) 0.8040(2) 0.0344(5) Uani 1 1 d . . . . .
O2 O 0.3449(2) 0.50087(16) 0.8522(2) 0.0395(5) Uani 1 1 d . . . . .
N2 N 0.5308(2) 0.63344(18) 0.6940(2) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.4620 0.6601 0.7394 0.031 Uiso 1 1 calc R . . . .
C1 C 0.5760(3) 0.7119(2) 0.6294(2) 0.0243(5) Uani 1 1 d . . . . .
H1 H 0.5460 0.7915 0.6264 0.029 Uiso 1 1 calc R . . . .
C3 C 0.5721(3) 0.5187(2) 0.7024(3) 0.0313(6) Uani 1 1 d . . . . .
H3 H 0.5385 0.4647 0.7503 0.038 Uiso 1 1 calc R . . . .
C4A C 0.7097(3) 0.5600(2) 0.5713(2) 0.0246(5) Uani 1 1 d . . . . .
C4 C 0.6600(3) 0.4805(2) 0.6436(3) 0.0303(6) Uani 1 1 d . . . . .
H4 H 0.6884 0.4002 0.6508 0.036 Uiso 1 1 calc R . . . .
C5 C 0.7984(3) 0.5264(2) 0.5037(3) 0.0317(6) Uani 1 1 d . . . . .
H5 H 0.8276 0.4467 0.5052 0.038 Uiso 1 1 calc R . . . .
C6 C 0.8420(3) 0.6090(2) 0.4361(3) 0.0334(6) Uani 1 1 d . . . . .
H6 H 0.9013 0.5857 0.3906 0.040 Uiso 1 1 calc R . . . .
C7 C 0.8006(3) 0.7280(3) 0.4326(3) 0.0314(6) Uani 1 1 d . . . . .
H7 H 0.8331 0.7837 0.3858 0.038 Uiso 1 1 calc R . . . .
C8A C 0.6669(2) 0.6798(2) 0.5656(2) 0.0217(5) Uani 1 1 d . . . . .
C8 C 0.7144(3) 0.7638(2) 0.4958(2) 0.0273(5) Uani 1 1 d . . . . .
H8 H 0.6865 0.8440 0.4932 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3005(3) 0.6020(2) 0.8383(2) 0.0237(5) Uani 1 1 d . . . . .
C10 C 0.1629(3) 0.62726(19) 0.8684(2) 0.0208(5) 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
Cl1 C10 1.763(2) . ?
Cl2 C10 1.784(2) . ?
Cl3 C10 1.772(2) . ?
O1 C9 1.256(3) . ?
O2 C9 1.222(3) . ?
N2 H2 1.0400 . ?
N2 C1 1.324(3) . ?
N2 C3 1.361(3) . ?
C1 H1 0.9500 . ?
C1 C8A 1.397(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.350(4) . ?
C4A C4 1.416(4) . ?
C4A C5 1.413(4) . ?
C4A C8A 1.422(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.370(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.364(4) . ?
C8A C8 1.417(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.570(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
C1 N2 H2 119.2 . . ?
C1 N2 C3 121.6(2) . . ?
C3 N2 H2 119.2 . . ?
N2 C1 H1 119.4 . . ?
N2 C1 C8A 121.2(2) . . ?
C8A C1 H1 119.4 . . ?
N2 C3 H3 119.5 . . ?
C4 C3 N2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C4 C4A C8A 118.1(2) . . ?
C5 C4A C4 123.6(2) . . ?
C5 C4A C8A 118.4(2) . . ?
C3 C4 C4A 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C4A C4 H4 120.0 . . ?
C4A C5 H5 120.1 . . ?
C6 C5 C4A 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C1 C8A C4A 118.2(2) . . ?
C1 C8A C8 121.1(2) . . ?
C8 C8A C4A 120.7(2) . . ?
C7 C8 C8A 119.0(2) . . ?
C7 C8 H8 120.5 . . ?
C8A C8 H8 120.5 . . ?
O1 C9 C10 113.7(2) . . ?
O2 C9 O1 129.0(2) . . ?
O2 C9 C10 117.3(2) . . ?
Cl1 C10 Cl2 108.35(12) . . ?
Cl1 C10 Cl3 107.83(13) . . ?
Cl3 C10 Cl2 108.59(12) . . ?
C9 C10 Cl1 112.75(16) . . ?
C9 C10 Cl2 108.00(16) . . ?
C9 C10 Cl3 111.22(16) . . ?

_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_13
_database_code_depnum_ccdc_archive 'CCDC 2000988'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        13
_chemical_name_common            Benzoquinoline+Dichloroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 H Cl2 O2, C2 H2 Cl2 O2'
_chemical_formula_sum            'C17 H13 Cl4 N O4'
_chemical_formula_weight         437.08

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4155(3)
_cell_length_b                   11.3195(5)
_cell_length_c                   19.7432(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.939(2)
_cell_angle_gamma                90
_cell_volume                     1878.25(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4984
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.653
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10664
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3787
_reflns_number_gt                2567
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0396P)²+1.4530P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6162(3) 0.53984(18) 0.39351(12) 0.0441(6) Uani 1 1 d . . . . .
H1N H 0.650285 0.627154 0.386633 0.053 Uiso 1 1 calc R U . . .
C1A C 0.6702(3) 0.4830(2) 0.45101(14) 0.0392(6) Uani 1 1 d . . . . .
C2 C 0.5221(4) 0.4893(3) 0.34579(16) 0.0545(8) Uani 1 1 d . . . . .
H2 H 0.488337 0.533445 0.306744 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4730(4) 0.3743(3) 0.35198(18) 0.0576(8) Uani 1 1 d . . . . .
H3 H 0.405752 0.338545 0.317714 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5230(4) 0.3128(2) 0.40848(18) 0.0553(9) Uani 1 1 d . . . . .
H4 H 0.490170 0.233064 0.413453 0.066 Uiso 1 1 calc R U . . .
C4A C 0.6220(3) 0.3650(2) 0.45942(16) 0.0466(7) Uani 1 1 d . . . . .
C5 C 0.6727(4) 0.3045(3) 0.51976(19) 0.0632(9) Uani 1 1 d . . . . .
H5 H 0.639670 0.225310 0.526543 0.076 Uiso 1 1 calc R U . . .
C6 C 0.7667(5) 0.3580(3) 0.56716(19) 0.0686(10) Uani 1 1 d . . . . .
H6 H 0.799401 0.315410 0.606914 0.082 Uiso 1 1 calc R U . . .
C6A C 0.8196(4) 0.4776(3) 0.55992(16) 0.0542(8) Uani 1 1 d . . . . .
C7 C 0.9154(5) 0.5345(3) 0.6103(2) 0.0735(11) Uani 1 1 d . . . . .
H7 H 0.948651 0.492094 0.650026 0.088 Uiso 1 1 calc R U . . .
C8 C 0.9618(5) 0.6482(4) 0.6037(2) 0.0774(11) Uani 1 1 d . . . . .
H8 H 1.026447 0.684558 0.638570 0.093 Uiso 1 1 calc R U . . .
C9 C 0.9147(4) 0.7119(3) 0.5457(2) 0.0687(10) Uani 1 1 d . . . . .
H9 H 0.947823 0.791593 0.541055 0.082 Uiso 1 1 calc R U . . .
C10 C 0.8209(4) 0.6598(2) 0.49557(17) 0.0530(8) Uani 1 1 d . . . . .
H10 H 0.789084 0.703921 0.456243 0.064 Uiso 1 1 calc R U . . .
C10A C 0.7711(3) 0.5421(2) 0.50146(15) 0.0428(7) Uani 1 1 d . . . . .
Cl1 Cl 0.73431(10) 1.08620(6) 0.31222(5) 0.0619(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68275(16) 0.98858(9) 0.44473(5) 0.0947(4) Uani 1 1 d . . . . .
O1 O 0.6152(3) 0.76781(17) 0.36154(12) 0.0667(7) Uani 1 1 d . . . . .
O2 O 0.7997(3) 0.83800(16) 0.29577(13) 0.0623(6) Uani 1 1 d . . . . .
C11 C 0.6920(3) 0.8474(2) 0.33585(15) 0.0418(7) Uani 1 1 d . . . . .
C12 C 0.6410(4) 0.9723(2) 0.35665(15) 0.0451(7) Uani 1 1 d . . . . .
H12 H 0.523366 0.979409 0.347571 0.054 Uiso 1 1 calc R U . . .
Cl3 Cl 0.76538(10) 0.35408(6) 0.22820(5) 0.0627(3) Uani 1 1 d . . . . .
Cl4 Cl 0.85562(15) 0.46026(8) 0.10269(5) 0.0867(4) Uani 1 1 d . . . . .
O3 O 0.8909(3) 0.63839(18) 0.25916(12) 0.0606(6) Uani 1 1 d . . . . .
H3O H 0.847(5) 0.717(4) 0.273(2) 0.111(14) Uiso 1 1 d . . . . .
O4 O 0.6724(3) 0.6219(2) 0.19382(15) 0.0870(9) Uani 1 1 d . . . . .
C13 C 0.7998(3) 0.5874(2) 0.21442(15) 0.0426(7) Uani 1 1 d . . . . .
C14 C 0.8705(3) 0.4709(2) 0.19135(15) 0.0434(7) Uani 1 1 d . . . . .
H14 H 0.985065 0.466861 0.207326 0.052 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.329(4) . ?
N1 C1A 1.362(3) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.409(4) . ?
C1A C10A 1.439(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.403(4) . ?
C4 H4 0.9500 . ?
C4A C5 1.421(4) . ?
C5 C6 1.339(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.434(5) . ?
C6 H6 0.9500 . ?
C6A C7 1.404(5) . ?
C6A C10A 1.408(4) . ?
C7 C8 1.352(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.368(4) . ?
C9 H9 0.9500 . ?
C10 C10A 1.404(4) . ?
C10 H10 0.9500 . ?
Cl1 C12 1.766(3) . ?
Cl2 C12 1.766(3) . ?
O1 C11 1.233(3) . ?
O2 C11 1.238(3) . ?
C11 C12 1.539(4) . ?
C12 H12 1.0000 . ?
Cl3 C14 1.768(3) . ?
Cl4 C14 1.753(3) . ?
O3 C13 1.277(3) . ?
O3 H3O 1.00(4) . ?
O4 C13 1.192(3) . ?
C13 C14 1.526(4) . ?
C14 H14 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
C2 N1 C1A 123.3(2) . . ?
C2 N1 H1N 118.4 . . ?
C1A N1 H1N 118.4 . . ?
N1 C1A C4A 117.4(3) . . ?
N1 C1A C10A 121.1(2) . . ?
C4A C1A C10A 121.5(3) . . ?
N1 C2 C3 121.1(3) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C4A 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C1A 118.6(3) . . ?
C4 C4A C5 122.7(3) . . ?
C1A C4A C5 118.7(3) . . ?
C6 C5 C4A 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C6A 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C6A C6 H6 118.9 . . ?
C7 C6A C10A 118.3(3) . . ?
C7 C6A C6 122.2(3) . . ?
C10A C6A C6 119.5(3) . . ?
C8 C7 C6A 121.8(4) . . ?
C8 C7 H7 119.1 . . ?
C6A C7 H7 119.1 . . ?
C7 C8 C9 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C10A 120.9(3) . . ?
C9 C10 H10 119.6 . . ?
C10A C10 H10 119.6 . . ?
C10 C10A C6A 119.0(3) . . ?
C10 C10A C1A 123.5(3) . . ?
C6A C10A C1A 117.5(3) . . ?
O1 C11 O2 128.0(3) . . ?
O1 C11 C12 113.7(3) . . ?
O2 C11 C12 118.2(2) . . ?
C11 C12 Cl2 108.33(19) . . ?
C11 C12 Cl1 113.6(2) . . ?
Cl2 C12 Cl1 109.97(15) . . ?
C11 C12 H12 108.3 . . ?
Cl2 C12 H12 108.3 . . ?
Cl1 C12 H12 108.3 . . ?
C13 O3 H3O 112(2) . . ?
O4 C13 O3 125.8(3) . . ?
O4 C13 C14 122.6(3) . . ?
O3 C13 C14 111.5(2) . . ?
C13 C14 Cl4 110.4(2) . . ?
C13 C14 Cl3 108.2(2) . . ?
Cl4 C14 Cl3 110.34(14) . . ?
C13 C14 H14 109.3 . . ?
Cl4 C14 H14 109.3 . . ?
Cl3 C14 H14 109.3 . . ?

_refine_diff_density_max         0.335
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2000981'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        6
_chemical_name_common            Acridine+Benzenesulfonate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C6 H5 O3 S'
_chemical_formula_sum            'C19 H15 N O3 S'
_chemical_formula_weight         337.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.1261(2)
_cell_length_b                   9.7581(4)
_cell_length_c                   22.8711(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.978(2)
_cell_angle_gamma                90
_cell_volume                     1590.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    4832
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.999

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.221
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10920
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.269
_diffrn_reflns_theta_max         26.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3197
_reflns_number_gt                2497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+1.3230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3197
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N10 N 0.7503(2) 0.55408(19) 0.52139(8) 0.0261(4) Uani 1 1 d . . . . .
H10N H 0.743859 0.619052 0.557340 0.031 Uiso 1 1 calc R U . . .
C1 C 0.8676(3) 0.5775(3) 0.36547(10) 0.0352(6) Uani 1 1 d . . . . .
H1 H 0.876590 0.520709 0.331899 0.042 Uiso 1 1 calc R U . . .
C2 C 0.9061(3) 0.7125(3) 0.36148(12) 0.0406(6) Uani 1 1 d . . . . .
H2 H 0.939289 0.750585 0.324851 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8974(3) 0.7981(3) 0.41138(12) 0.0404(6) Uani 1 1 d . . . . .
H3 H 0.926610 0.892682 0.407671 0.049 Uiso 1 1 calc R U . . .
C4 C 0.8482(3) 0.7481(3) 0.46461(11) 0.0337(5) Uani 1 1 d . . . . .
H4 H 0.844656 0.806372 0.497841 0.040 Uiso 1 1 calc R U . . .
C4A C 0.8026(3) 0.6079(2) 0.46933(10) 0.0257(5) Uani 1 1 d . . . . .
C5 C 0.6508(3) 0.3711(3) 0.58458(10) 0.0316(5) Uani 1 1 d . . . . .
H5 H 0.641534 0.431768 0.616904 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6111(3) 0.2348(3) 0.59053(11) 0.0357(6) Uani 1 1 d . . . . .
H6 H 0.572149 0.201360 0.627403 0.043 Uiso 1 1 calc R U . . .
C7 C 0.6266(3) 0.1425(3) 0.54357(11) 0.0373(6) Uani 1 1 d . . . . .
H7 H 0.600427 0.048065 0.549313 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6787(3) 0.1879(3) 0.48989(11) 0.0327(5) Uani 1 1 d . . . . .
H8 H 0.688791 0.124901 0.458420 0.039 Uiso 1 1 calc R U . . .
C8A C 0.7182(3) 0.3288(2) 0.48079(10) 0.0259(5) Uani 1 1 d . . . . .
C9 C 0.7723(3) 0.3817(2) 0.42677(10) 0.0266(5) Uani 1 1 d . . . . .
H9 H 0.781076 0.321917 0.394142 0.032 Uiso 1 1 calc R U . . .
C9A C 0.8133(3) 0.5197(2) 0.41993(10) 0.0270(5) Uani 1 1 d . . . . .
C10A C 0.7060(3) 0.4201(2) 0.52893(9) 0.0256(5) Uani 1 1 d . . . . .
S1 S 0.85545(8) 0.80375(6) 0.64683(3) 0.02889(17) Uani 1 1 d . . . . .
O1 O 0.7350(3) 0.6993(2) 0.61993(8) 0.0489(5) Uani 1 1 d . . . . .
O2 O 0.9574(3) 0.8811(2) 0.60443(9) 0.0549(6) Uani 1 1 d . . . . .
O3 O 0.9713(3) 0.7484(2) 0.69339(9) 0.0580(6) Uani 1 1 d . . . . .
C11 C 0.6975(3) 0.9189(2) 0.68081(9) 0.0235(4) Uani 1 1 d . . . . .
C12 C 0.7681(3) 1.0235(2) 0.71553(10) 0.0295(5) Uani 1 1 d . . . . .
H12 H 0.899868 1.034691 0.720498 0.035 Uiso 1 1 calc R U . . .
C13 C 0.6459(3) 1.1118(3) 0.74300(10) 0.0370(6) Uani 1 1 d . . . . .
H13 H 0.693775 1.184344 0.766574 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4535(4) 1.0946(3) 0.73620(11) 0.0418(6) Uani 1 1 d . . . . .
H14 H 0.369701 1.154262 0.755659 0.050 Uiso 1 1 calc R U . . .
C15 C 0.3840(3) 0.9906(3) 0.70114(12) 0.0415(6) Uani 1 1 d . . . . .
H15 H 0.252295 0.979248 0.696260 0.050 Uiso 1 1 calc R U . . .
C16 C 0.5055(3) 0.9030(2) 0.67307(10) 0.0315(5) Uani 1 1 d . . . . .
H16 H 0.457524 0.832138 0.648573 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N10 C10A 1.356(3) . ?
N10 C4A 1.359(3) . ?
N10 H10N 1.0400 . ?
C1 C2 1.350(4) . ?
C1 C9A 1.426(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(4) . ?
C3 H3 0.9500 . ?
C4 C4A 1.410(3) . ?
C4 H4 0.9500 . ?
C4A C9A 1.423(3) . ?
C5 C6 1.368(4) . ?
C5 C10A 1.421(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.363(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.419(3) . ?
C8 H8 0.9500 . ?
C8A C9 1.399(3) . ?
C8A C10A 1.420(3) . ?
C9 C9A 1.388(3) . ?
C9 H9 0.9500 . ?
S1 O2 1.4356(19) . ?
S1 O3 1.441(2) . ?
S1 O1 1.4615(19) . ?
S1 C11 1.778(2) . ?
C11 C12 1.383(3) . ?
C11 C16 1.385(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 H16 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
C10A N10 C4A 123.48(19) . . ?
C10A N10 H10N 118.3 . . ?
C4A N10 H10N 118.3 . . ?
C2 C1 C9A 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C9A C1 H1 119.9 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C4A 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C4A C4 H4 120.7 . . ?
N10 C4A C4 120.6(2) . . ?
N10 C4A C9A 118.8(2) . . ?
C4 C4A C9A 120.7(2) . . ?
C6 C5 C10A 118.5(2) . . ?
C6 C5 H5 120.8 . . ?
C10A C5 H5 120.8 . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C8A 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C9 C8A C8 123.0(2) . . ?
C9 C8A C10A 118.3(2) . . ?
C8 C8A C10A 118.6(2) . . ?
C9A C9 C8A 121.3(2) . . ?
C9A C9 H9 119.4 . . ?
C8A C9 H9 119.4 . . ?
C9 C9A C4A 118.9(2) . . ?
C9 C9A C1 122.9(2) . . ?
C4A C9A C1 118.2(2) . . ?
N10 C10A C8A 119.3(2) . . ?
N10 C10A C5 120.4(2) . . ?
C8A C10A C5 120.3(2) . . ?
O2 S1 O3 113.96(13) . . ?
O2 S1 O1 112.49(12) . . ?
O3 S1 O1 111.99(13) . . ?
O2 S1 C11 107.11(11) . . ?
O3 S1 C11 105.82(11) . . ?
O1 S1 C11 104.66(10) . . ?
C12 C11 C16 120.3(2) . . ?
C12 C11 S1 119.38(16) . . ?
C16 C11 S1 120.29(17) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 119.8(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.052

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

data_11
_database_code_depnum_ccdc_archive 'CCDC 2000986'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        11
_chemical_name_common            Benzoquinoline+Trichloroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 Cl3 O2'
_chemical_formula_sum            'C15 H10 Cl3 N O2'
_chemical_formula_weight         342.59

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.6910(2)
_cell_length_b                   24.1354(7)
_cell_length_c                   18.5026(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.611(2)
_cell_angle_gamma                90
_cell_volume                     2984.88(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    7316
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      30.508

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.616
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13612
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.360
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5345
_reflns_number_gt                4025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0747P)²+4.1538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5345
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1727
_refine_ls_wR_factor_gt          0.1612
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8611(4) 0.54530(12) 0.15949(15) 0.0276(6) Uani 1 1 d . . . . .
H1N H 0.860112 0.504461 0.177412 0.033 Uiso 1 1 calc R U . . .
C1A C 0.8622(4) 0.58668(14) 0.20938(18) 0.0243(7) Uani 1 1 d . . . . .
C2 C 0.8613(5) 0.55494(16) 0.08843(19) 0.0320(8) Uani 1 1 d . . . . .
H2 H 0.861235 0.524566 0.055770 0.038 Uiso 1 1 calc R U . . .
C3 C 0.8616(5) 0.60810(16) 0.0617(2) 0.0343(8) Uani 1 1 d . . . . .
H3 H 0.861549 0.614675 0.011126 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8620(5) 0.65153(16) 0.1098(2) 0.0335(8) Uani 1 1 d . . . . .
H4 H 0.861831 0.688486 0.092102 0.040 Uiso 1 1 calc R U . . .
C4A C 0.8626(5) 0.64191(14) 0.18493(19) 0.0272(7) Uani 1 1 d . . . . .
C5 C 0.8622(5) 0.68587(15) 0.2363(2) 0.0340(9) Uani 1 1 d . . . . .
H5 H 0.864172 0.723168 0.219902 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8591(5) 0.67534(16) 0.3078(2) 0.0350(9) Uani 1 1 d . . . . .
H6 H 0.857713 0.705303 0.341048 0.042 Uiso 1 1 calc R U . . .
C6A C 0.8579(5) 0.61955(15) 0.3343(2) 0.0307(8) Uani 1 1 d . . . . .
C7 C 0.8516(5) 0.60889(18) 0.4093(2) 0.0375(9) Uani 1 1 d . . . . .
H7 H 0.845671 0.639005 0.442210 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8538(6) 0.55583(19) 0.4351(2) 0.0409(10) Uani 1 1 d . . . . .
H8 H 0.850488 0.549351 0.485652 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8611(5) 0.51111(17) 0.3874(2) 0.0365(9) Uani 1 1 d . . . . .
H9 H 0.863526 0.474359 0.405850 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8648(5) 0.51980(15) 0.31416(19) 0.0299(8) Uani 1 1 d . . . . .
H10 H 0.869147 0.489021 0.282259 0.036 Uiso 1 1 calc R U . . .
C10A C 0.8620(5) 0.57413(14) 0.28588(18) 0.0266(7) Uani 1 1 d . . . . .
Cl1 Cl 0.5167(2) 0.33555(6) 0.11677(9) 0.0746(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9134(2) 0.30250(5) 0.08553(8) 0.0699(4) Uani 1 1 d . . . . .
Cl3 Cl 0.8135(3) 0.32908(6) 0.23131(7) 0.0906(6) Uani 1 1 d . . . . .
O1 O 0.8445(6) 0.43743(11) 0.17962(15) 0.0610(9) Uani 1 1 d . . . . .
O2 O 0.8286(7) 0.42250(13) 0.06249(16) 0.0721(11) Uani 1 1 d . . . . .
C11 C 0.8231(6) 0.40914(15) 0.12517(19) 0.0323(8) Uani 1 1 d . . . . .
C12 C 0.7764(7) 0.34640(16) 0.1403(2) 0.0406(10) Uani 1 1 d . . . . .
N13 N 0.3703(4) 0.54818(12) 0.32938(15) 0.0261(6) Uani 1 1 d . . . . .
H13N H 0.369864 0.586556 0.354929 0.031 Uiso 1 1 calc R U . . .
C13A C 0.3633(5) 0.54661(14) 0.25527(18) 0.0249(7) Uani 1 1 d . . . . .
C14 C 0.3778(5) 0.50264(15) 0.3701(2) 0.0312(8) Uani 1 1 d . . . . .
H14 H 0.385592 0.505929 0.421305 0.037 Uiso 1 1 calc R U . . .
C15 C 0.3743(6) 0.45062(16) 0.3387(2) 0.0364(9) Uani 1 1 d . . . . .
H15 H 0.378147 0.418271 0.367975 0.044 Uiso 1 1 calc R U . . .
C16 C 0.3651(5) 0.44644(16) 0.2649(2) 0.0372(9) Uani 1 1 d . . . . .
H16 H 0.362186 0.410900 0.242806 0.045 Uiso 1 1 calc R U . . .
C16A C 0.3599(5) 0.49448(15) 0.22128(19) 0.0302(8) Uani 1 1 d . . . . .
C17 C 0.3538(5) 0.49158(17) 0.1439(2) 0.0368(9) Uani 1 1 d . . . . .
H17 H 0.350186 0.456511 0.120543 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3530(5) 0.53838(17) 0.10396(19) 0.0343(9) Uani 1 1 d . . . . .
H18 H 0.349468 0.535643 0.052697 0.041 Uiso 1 1 calc R U . . .
C18A C 0.3574(5) 0.59169(16) 0.13675(19) 0.0305(8) Uani 1 1 d . . . . .
C19 C 0.3578(5) 0.64027(17) 0.0944(2) 0.0356(9) Uani 1 1 d . . . . .
H19 H 0.355401 0.637268 0.043167 0.043 Uiso 1 1 calc R U . . .
C20 C 0.3614(5) 0.69146(17) 0.1256(2) 0.0370(9) Uani 1 1 d . . . . .
H20 H 0.362946 0.723636 0.096021 0.044 Uiso 1 1 calc R U . . .
C21 C 0.3629(5) 0.69683(16) 0.2010(2) 0.0355(8) Uani 1 1 d . . . . .
H21 H 0.364511 0.732649 0.222283 0.043 Uiso 1 1 calc R U . . .
C22 C 0.3621(5) 0.65044(15) 0.24449(19) 0.0295(8) Uani 1 1 d . . . . .
H22 H 0.362525 0.654463 0.295574 0.035 Uiso 1 1 calc R U . . .
C22A C 0.3607(4) 0.59719(15) 0.21356(18) 0.0262(7) Uani 1 1 d . . . . .
Cl4 Cl 0.5084(2) 0.69513(5) 0.57655(8) 0.0752(5) Uani 1 1 d . . . . .
Cl5 Cl 0.1107(2) 0.65077(5) 0.59319(6) 0.0664(4) Uani 1 1 d . . . . .
Cl6 Cl 0.17958(15) 0.72931(4) 0.48193(5) 0.0409(3) Uani 1 1 d . . . . .
O3 O 0.3508(4) 0.63513(11) 0.41477(13) 0.0378(6) Uani 1 1 d . . . . .
O4 O 0.3755(4) 0.57878(11) 0.51117(14) 0.0433(7) Uani 1 1 d . . . . .
C23 C 0.3422(5) 0.62264(15) 0.47949(18) 0.0286(8) Uani 1 1 d . . . . .
C24 C 0.2858(6) 0.67242(15) 0.5297(2) 0.0363(9) 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 1.335(4) . ?
N1 C1A 1.360(4) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.408(5) . ?
C1A C10A 1.447(5) . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.410(5) . ?
C4 H4 0.9500 . ?
C4A C5 1.424(5) . ?
C5 C6 1.348(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.433(5) . ?
C6 H6 0.9500 . ?
C6A C7 1.414(5) . ?
C6A C10A 1.417(5) . ?
C7 C8 1.366(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C10A 1.412(5) . ?
C10 H10 0.9500 . ?
Cl1 C12 1.791(5) . ?
Cl2 C12 1.753(4) . ?
Cl3 C12 1.742(4) . ?
O1 C11 1.220(4) . ?
O2 C11 1.206(4) . ?
C11 C12 1.574(5) . ?
N13 C14 1.332(4) . ?
N13 C13A 1.370(4) . ?
N13 H13N 1.0400 . ?
C13A C16A 1.407(5) . ?
C13A C22A 1.444(5) . ?
C14 C15 1.383(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9500 . ?
C16 C16A 1.412(5) . ?
C16 H16 0.9500 . ?
C16A C17 1.432(5) . ?
C17 C18 1.350(6) . ?
C17 H17 0.9500 . ?
C18 C18A 1.422(5) . ?
C18 H18 0.9500 . ?
C18A C19 1.410(5) . ?
C18A C22A 1.427(5) . ?
C19 C20 1.363(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 C22A 1.407(5) . ?
C22 H22 0.9500 . ?
Cl4 C24 1.776(4) . ?
Cl5 C24 1.775(4) . ?
Cl6 C24 1.765(4) . ?
O3 C23 1.239(4) . ?
O4 C23 1.225(4) . ?
C23 C24 1.575(5) . ?

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 C1A 122.7(3) . . ?
C2 N1 H1N 118.6 . . ?
C1A N1 H1N 118.7 . . ?
N1 C1A C4A 118.5(3) . . ?
N1 C1A C10A 120.7(3) . . ?
C4A C1A C10A 120.8(3) . . ?
N1 C2 C3 121.1(3) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C4A 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C1A C4A C4 118.2(3) . . ?
C1A C4A C5 119.4(3) . . ?
C4 C4A C5 122.4(3) . . ?
C6 C5 C4A 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4A C5 H5 119.5 . . ?
C5 C6 C6A 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
C6A C6 H6 119.6 . . ?
C7 C6A C10A 118.8(3) . . ?
C7 C6A C6 120.5(3) . . ?
C10A C6A C6 120.7(3) . . ?
C8 C7 C6A 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C6A C7 H7 119.6 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C10A 120.5(3) . . ?
C9 C10 H10 119.8 . . ?
C10A C10 H10 119.8 . . ?
C10 C10A C6A 119.0(3) . . ?
C10 C10A C1A 123.8(3) . . ?
C6A C10A C1A 117.2(3) . . ?
O2 C11 O1 129.6(4) . . ?
O2 C11 C12 116.3(3) . . ?
O1 C11 C12 114.1(3) . . ?
C11 C12 Cl3 112.5(3) . . ?
C11 C12 Cl2 111.4(3) . . ?
Cl3 C12 Cl2 111.0(2) . . ?
C11 C12 Cl1 107.2(3) . . ?
Cl3 C12 Cl1 107.1(2) . . ?
Cl2 C12 Cl1 107.4(2) . . ?
C14 N13 C13A 122.8(3) . . ?
C14 N13 H13N 118.6 . . ?
C13A N13 H13N 118.6 . . ?
N13 C13A C16A 118.1(3) . . ?
N13 C13A C22A 120.7(3) . . ?
C16A C13A C22A 121.2(3) . . ?
N13 C14 C15 120.8(3) . . ?
N13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C16A 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C16A C16 H16 119.7 . . ?
C13A C16A C16 118.6(3) . . ?
C13A C16A C17 119.3(3) . . ?
C16 C16A C17 122.0(3) . . ?
C18 C17 C16A 120.4(4) . . ?
C18 C17 H17 119.8 . . ?
C16A C17 H17 119.8 . . ?
C17 C18 C18A 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C18A C18 H18 119.2 . . ?
C19 C18A C18 121.0(3) . . ?
C19 C18A C22A 118.4(3) . . ?
C18 C18A C22A 120.5(3) . . ?
C20 C19 C18A 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C18A C19 H19 119.4 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C22A 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C22A C22 H22 119.9 . . ?
C22 C22A C18A 119.3(3) . . ?
C22 C22A C13A 123.7(3) . . ?
C18A C22A C13A 116.9(3) . . ?
O4 C23 O3 131.1(3) . . ?
O4 C23 C24 114.8(3) . . ?
O3 C23 C24 114.1(3) . . ?
C23 C24 Cl6 113.6(2) . . ?
C23 C24 Cl5 110.4(3) . . ?
Cl6 C24 Cl5 107.3(2) . . ?
C23 C24 Cl4 107.8(3) . . ?
Cl6 C24 Cl4 108.3(2) . . ?
Cl5 C24 Cl4 109.4(2) . . ?

_refine_diff_density_max         1.405
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2000985'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        10
_chemical_name_common            Benzoquinoline+Trifluoroacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 F3 O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0948(10)
_cell_length_b                   5.0687(3)
_cell_length_c                   24.9448(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.411(3)
_cell_angle_gamma                90
_cell_volume                     1276.33(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2066
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      29.131

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.131
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4542
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4994
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         25.196
_diffrn_reflns_theta_full        25.196
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2203
_reflns_number_gt                1351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+1.3875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2203
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4730(2) 0.4752(5) 0.39620(10) 0.0338(6) Uani 1 1 d . . . . .
H1N H 0.557084 0.379483 0.382212 0.041 Uiso 1 1 calc R U . . .
C1A C 0.4197(3) 0.6734(6) 0.36593(13) 0.0320(7) Uani 1 1 d . . . . .
C2 C 0.4226(3) 0.3993(7) 0.44259(13) 0.0383(8) Uani 1 1 d . . . . .
H2 H 0.463123 0.258774 0.461826 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3113(3) 0.5220(7) 0.46355(14) 0.0469(9) Uani 1 1 d . . . . .
H3 H 0.275170 0.466167 0.496726 0.056 Uiso 1 1 calc R U . . .
C4 C 0.2553(3) 0.7242(7) 0.43545(14) 0.0432(9) Uani 1 1 d . . . . .
H4 H 0.179863 0.811795 0.449465 0.052 Uiso 1 1 calc R U . . .
C4A C 0.3076(3) 0.8052(6) 0.38590(13) 0.0354(8) Uani 1 1 d . . . . .
C5 C 0.2510(3) 1.0163(7) 0.35538(14) 0.0414(8) Uani 1 1 d . . . . .
H5 H 0.175563 1.107029 0.368562 0.050 Uiso 1 1 calc R U . . .
C6 C 0.3036(3) 1.0874(7) 0.30818(14) 0.0399(8) Uani 1 1 d . . . . .
H6 H 0.265778 1.231134 0.289030 0.048 Uiso 1 1 calc R U . . .
C6A C 0.4149(3) 0.9529(6) 0.28598(13) 0.0346(8) Uani 1 1 d . . . . .
C7 C 0.4648(3) 1.0220(7) 0.23508(14) 0.0408(8) Uani 1 1 d . . . . .
H7 H 0.426727 1.165963 0.216085 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5667(3) 0.8853(7) 0.21287(14) 0.0424(9) Uani 1 1 d . . . . .
H8 H 0.598075 0.931777 0.178319 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6248(3) 0.6775(7) 0.24087(14) 0.0414(8) Uani 1 1 d . . . . .
H9 H 0.695639 0.582570 0.225034 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5817(3) 0.6069(6) 0.29096(13) 0.0369(8) Uani 1 1 d . . . . .
H10 H 0.623692 0.466319 0.309668 0.044 Uiso 1 1 calc R U . . .
C10A C 0.4752(3) 0.7429(6) 0.31468(13) 0.0325(7) Uani 1 1 d . . . . .
F1 F 0.8956(2) -0.2118(6) 0.45678(12) 0.0933(11) Uani 1 1 d . . . . .
F2 F 0.9458(2) 0.1710(5) 0.43134(12) 0.0836(9) Uani 1 1 d . . . . .
F3 F 0.9129(2) -0.1244(5) 0.37369(10) 0.0744(8) Uani 1 1 d . . . . .
O1 O 0.6977(2) 0.2167(5) 0.38242(10) 0.0548(7) Uani 1 1 d . . . . .
O2 O 0.6457(2) -0.0623(5) 0.44884(10) 0.0517(7) Uani 1 1 d . . . . .
C11 C 0.7205(3) 0.0449(7) 0.41709(13) 0.0383(8) Uani 1 1 d . . . . .
C12 C 0.8672(3) -0.0346(7) 0.41982(14) 0.0430(9) 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 1.325(4) . ?
N1 C1A 1.365(4) . ?
N1 H1N 1.0400 . ?
C1A C4A 1.408(4) . ?
C1A C10A 1.443(4) . ?
C2 C3 1.389(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9500 . ?
C4 C4A 1.409(5) . ?
C4 H4 0.9500 . ?
C4A C5 1.430(5) . ?
C5 C6 1.345(5) . ?
C5 H5 0.9500 . ?
C6 C6A 1.429(5) . ?
C6 H6 0.9500 . ?
C6A C7 1.414(4) . ?
C6A C10A 1.418(4) . ?
C7 C8 1.361(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9500 . ?
C10 C10A 1.410(4) . ?
C10 H10 0.9500 . ?
F1 C12 1.317(4) . ?
F2 C12 1.340(4) . ?
F3 C12 1.324(4) . ?
O1 C11 1.247(4) . ?
O2 C11 1.225(4) . ?
C11 C12 1.536(5) . ?

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 C1A 123.0(3) . . ?
C2 N1 H1N 118.5 . . ?
C1A N1 H1N 118.5 . . ?
N1 C1A C4A 117.9(3) . . ?
N1 C1A C10A 121.0(3) . . ?
C4A C1A C10A 121.0(3) . . ?
N1 C2 C3 121.0(3) . . ?
N1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C4A 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C4A C4 H4 119.6 . . ?
C4 C4A C1A 118.7(3) . . ?
C4 C4A C5 122.3(3) . . ?
C1A C4A C5 119.1(3) . . ?
C6 C5 C4A 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
C5 C6 C6A 121.9(3) . . ?
C5 C6 H6 119.1 . . ?
C6A C6 H6 119.1 . . ?
C7 C6A C10A 119.0(3) . . ?
C7 C6A C6 121.1(3) . . ?
C10A C6A C6 119.9(3) . . ?
C8 C7 C6A 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6A C7 H7 119.5 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C10A 120.1(3) . . ?
C9 C10 H10 119.9 . . ?
C10A C10 H10 119.9 . . ?
C10 C10A C6A 118.7(3) . . ?
C10 C10A C1A 123.7(3) . . ?
C6A C10A C1A 117.5(3) . . ?
O2 C11 O1 130.3(3) . . ?
O2 C11 C12 117.0(3) . . ?
O1 C11 C12 112.8(3) . . ?
F1 C12 F3 107.4(3) . . ?
F1 C12 F2 104.7(3) . . ?
F3 C12 F2 104.1(3) . . ?
F1 C12 C11 114.5(3) . . ?
F3 C12 C11 113.2(3) . . ?
F2 C12 C11 112.0(3) . . ?

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.052

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

data_14
_database_code_depnum_ccdc_archive 'CCDC 2000989'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-05-04 deposited with the CCDC.	2020-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        14
_chemical_name_common            Benzoquinoline+Dibromoacetate
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N, C2 H Br2 O2, C2 H2 Br2 O2'
_chemical_formula_sum            'C17 H13 Br4 N O4'
_chemical_formula_weight         614.92

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'

_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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   4.3451(2)
_cell_length_b                   19.0711(5)
_cell_length_c                   23.2876(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1929.75(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2785
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      28.283

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.117
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    8.364
_shelx_estimated_absorpt_T_min   0.135
_shelx_estimated_absorpt_T_max   0.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4217
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18405
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.308
_diffrn_reflns_theta_max         26.249
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3887
_reflns_number_gt                3508
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0076P)²+3.1774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1327 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.227(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8864(10) 0.4185(2) 0.68041(16) 0.0244(9) Uani 1 1 d . . . . .
H1 H 0.807467 0.372020 0.662241 0.029 Uiso 1 1 calc R U . . .
C1A C 0.7788(12) 0.4804(3) 0.6588(2) 0.0261(11) Uani 1 1 d . . . . .
C2 C 1.0884(13) 0.4144(3) 0.7238(2) 0.0296(12) Uani 1 1 d . . . . .
H2 H 1.158634 0.369912 0.736596 0.036 Uiso 1 1 calc R U . . .
C3 C 1.1942(13) 0.4746(3) 0.7498(2) 0.0317(13) Uani 1 1 d . . . . .
H3 H 1.338297 0.471956 0.780419 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0888(14) 0.5388(3) 0.7309(2) 0.0327(13) Uani 1 1 d . . . . .
H4 H 1.159564 0.580603 0.748821 0.039 Uiso 1 1 calc R U . . .
C4A C 0.8779(13) 0.5428(3) 0.6856(2) 0.0281(12) Uani 1 1 d . . . . .
C5 C 0.7618(14) 0.6085(3) 0.6648(2) 0.0328(13) Uani 1 1 d . . . . .
H5 H 0.824429 0.650960 0.682674 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5656(14) 0.6106(3) 0.6203(2) 0.0357(13) Uani 1 1 d . . . . .
H6 H 0.490719 0.654622 0.607408 0.043 Uiso 1 1 calc R U . . .
C6A C 0.4659(12) 0.5478(3) 0.5918(2) 0.0275(12) Uani 1 1 d . . . . .
C7 C 0.2614(14) 0.5506(3) 0.5447(2) 0.0348(13) Uani 1 1 d . . . . .
H7 H 0.187317 0.594671 0.531613 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1699(13) 0.4910(3) 0.5180(2) 0.0371(14) Uani 1 1 d . . . . .
H8 H 0.032135 0.493875 0.486385 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2749(15) 0.4255(3) 0.5362(2) 0.0350(13) Uani 1 1 d . . . . .
H9 H 0.209724 0.384190 0.516937 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4723(13) 0.4210(3) 0.5819(2) 0.0288(13) Uani 1 1 d . . . . .
H10 H 0.543725 0.376438 0.594277 0.035 Uiso 1 1 calc R U . . .
C10A C 0.5697(12) 0.4817(3) 0.6106(2) 0.0246(11) Uani 1 1 d . . . . .
Br1 Br 0.30015(17) 0.22760(3) 0.56377(3) 0.04486(18) Uani 1 1 d . . . . .
Br2 Br 0.58379(17) 0.09605(3) 0.62669(2) 0.04192(17) Uani 1 1 d . . . . .
O2 O 0.5996(15) 0.2036(2) 0.72699(17) 0.0643(16) Uani 1 1 d . . . . .
O1 O 0.6813(12) 0.2861(2) 0.66273(18) 0.0529(13) Uani 1 1 d . . . . .
C11 C 0.5736(14) 0.2309(3) 0.6788(2) 0.0313(12) Uani 1 1 d . . . . .
C12 C 0.3795(14) 0.1857(3) 0.6374(2) 0.0309(12) Uani 1 1 d . . . . .
H12 H 0.176595 0.176526 0.656209 0.037 Uiso 1 1 calc R U . . .
Br3 Br 0.71883(15) 0.29334(3) 0.94850(2) 0.03776(16) Uani 1 1 d . . . . .
Br4 Br 0.87230(15) 0.44056(3) 0.89204(3) 0.04093(17) Uani 1 1 d . . . . .
O3 O 0.8587(12) 0.2599(2) 0.80929(18) 0.0494(12) Uani 1 1 d . . . . .
H3A H 0.766528 0.247950 0.779116 0.074 Uiso 1 1 calc R U . . .
O4 O 0.5248(10) 0.3477(3) 0.80857(18) 0.0474(12) Uani 1 1 d . . . . .
C13 C 0.7403(13) 0.3163(3) 0.8288(2) 0.0272(12) Uani 1 1 d . . . . .
C14 C 0.9036(12) 0.3412(3) 0.8830(2) 0.0266(11) Uani 1 1 d . . . . .
H14 H 1.125992 0.328055 0.880607 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.340(7) . ?
N1 C1A 1.367(6) . ?
N1 H1 1.0400 . ?
C1A C4A 1.411(7) . ?
C1A C10A 1.443(7) . ?
C2 C3 1.378(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(8) . ?
C3 H3 0.9500 . ?
C4 C4A 1.401(8) . ?
C4 H4 0.9500 . ?
C4A C5 1.435(8) . ?
C5 C6 1.342(8) . ?
C5 H5 0.9500 . ?
C6 C6A 1.436(8) . ?
C6 H6 0.9500 . ?
C6A C10A 1.410(7) . ?
C6A C7 1.412(8) . ?
C7 C8 1.355(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(8) . ?
C9 H9 0.9500 . ?
C10 C10A 1.401(7) . ?
C10 H10 0.9500 . ?
Br1 C12 1.923(5) . ?
Br2 C12 1.942(6) . ?
O2 C11 1.243(7) . ?
O1 C11 1.210(7) . ?
C11 C12 1.545(7) . ?
C12 H12 1.0000 . ?
Br3 C14 1.950(5) . ?
Br4 C14 1.911(5) . ?
O3 C13 1.276(7) . ?
O3 H3A 0.8400 . ?
O4 C13 1.207(7) . ?
C13 C14 1.525(7) . ?
C14 H14 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
C2 N1 C1A 123.5(5) . . ?
C2 N1 H1 118.2 . . ?
C1A N1 H1 118.2 . . ?
N1 C1A C4A 117.5(5) . . ?
N1 C1A C10A 121.1(5) . . ?
C4A C1A C10A 121.4(5) . . ?
N1 C2 C3 120.1(5) . . ?
N1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C4A 120.4(5) . . ?
C3 C4 H4 119.8 . . ?
C4A C4 H4 119.8 . . ?
C4 C4A C1A 119.2(5) . . ?
C4 C4A C5 122.1(5) . . ?
C1A C4A C5 118.7(5) . . ?
C6 C5 C4A 120.6(5) . . ?
C6 C5 H5 119.7 . . ?
C4A C5 H5 119.7 . . ?
C5 C6 C6A 121.7(5) . . ?
C5 C6 H6 119.2 . . ?
C6A C6 H6 119.2 . . ?
C10A C6A C7 118.5(5) . . ?
C10A C6A C6 120.3(5) . . ?
C7 C6A C6 121.2(5) . . ?
C8 C7 C6A 120.6(5) . . ?
C8 C7 H7 119.7 . . ?
C6A C7 H7 119.7 . . ?
C7 C8 C9 121.0(5) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C10A 120.6(5) . . ?
C9 C10 H10 119.7 . . ?
C10A C10 H10 119.7 . . ?
C10 C10A C6A 119.6(5) . . ?
C10 C10A C1A 123.2(5) . . ?
C6A C10A C1A 117.3(5) . . ?
O1 C11 O2 127.4(6) . . ?
O1 C11 C12 120.3(5) . . ?
O2 C11 C12 112.3(5) . . ?
C11 C12 Br1 115.0(4) . . ?
C11 C12 Br2 108.8(4) . . ?
Br1 C12 Br2 109.5(3) . . ?
C11 C12 H12 107.8 . . ?
Br1 C12 H12 107.8 . . ?
Br2 C12 H12 107.8 . . ?
C13 O3 H3A 109.5 . . ?
O4 C13 O3 126.3(5) . . ?
O4 C13 C14 121.9(5) . . ?
O3 C13 C14 111.7(5) . . ?
C13 C14 Br4 111.5(4) . . ?
C13 C14 Br3 108.0(4) . . ?
Br4 C14 Br3 110.4(2) . . ?
C13 C14 H14 108.9 . . ?
Br4 C14 H14 108.9 . . ?
Br3 C14 H14 108.9 . . ?

_refine_diff_density_max         0.747
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.075

