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

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

data_DLR08_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2124566'
loop_
_audit_author_name
_audit_author_address
'E Suresh'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 F N2 O'
_chemical_formula_weight         340.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.213(4)
_cell_length_b                   7.512(2)
_cell_length_c                   18.352(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.058(11)
_cell_angle_gamma                90
_cell_volume                     1539.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2132
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      22.75

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17598
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.1495
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         23.597
_diffrn_reflns_theta_full        23.597
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2315
_reflns_number_gt                1426
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2315
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1202
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1928
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.8748(2) 0.4266(3) 0.51818(12) 0.0398(7) Uani 1 1 d . . . . .
O1 O 0.7279(2) 0.4724(3) 0.39024(13) 0.0274(8) Uani 1 1 d . . . . .
N1 N 0.5197(3) 0.2562(4) 0.49243(17) 0.0255(8) Uani 1 1 d . . . . .
C1 C 0.8643(4) 0.4669(5) 0.5900(2) 0.0284(11) Uani 1 1 d . . . . .
N2 N 0.5674(3) 0.2641(4) 0.61169(17) 0.0264(9) Uani 1 1 d . . . . .
C2 C 0.9593(4) 0.5490(5) 0.6290(2) 0.0311(11) Uani 1 1 d . . . . .
H2 H 1.030383 0.575758 0.606659 0.037 Uiso 1 1 calc R U . . .
C3 C 0.9491(4) 0.5917(5) 0.7017(2) 0.0322(11) Uani 1 1 d . . . . .
H3 H 1.012582 0.651465 0.729423 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8457(4) 0.5466(5) 0.7336(2) 0.0312(11) Uani 1 1 d . . . . .
H4 H 0.839008 0.574183 0.783607 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7527(4) 0.4624(5) 0.6935(2) 0.0288(11) Uani 1 1 d . . . . .
H5 H 0.682853 0.431265 0.716419 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7596(4) 0.4215(5) 0.6191(2) 0.0252(10) Uani 1 1 d . . . . .
C7 C 0.6578(4) 0.3413(5) 0.5763(2) 0.0270(10) Uani 1 1 d . . . . .
C8 C 0.6298(4) 0.3380(5) 0.4994(2) 0.0247(10) Uani 1 1 d . . . . .
C9 C 0.6438(4) 0.3821(5) 0.4256(2) 0.0252(10) Uani 1 1 d . . . . .
C10 C 0.5467(4) 0.3255(5) 0.3784(2) 0.0262(10) Uani 1 1 d . . . . .
C11 C 0.4614(4) 0.2453(5) 0.4230(2) 0.0254(10) Uani 1 1 d . . . . .
C12 C 0.3481(4) 0.1711(5) 0.4216(2) 0.0276(11) Uani 1 1 d . . . . .
H12 H 0.300943 0.154607 0.376487 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3041(4) 0.1206(5) 0.4879(2) 0.0307(11) Uani 1 1 d . . . . .
H13 H 0.226322 0.069684 0.486192 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3680(4) 0.1411(5) 0.5563(2) 0.0277(11) Uani 1 1 d . . . . .
H14 H 0.334318 0.105590 0.599723 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4823(4) 0.2148(5) 0.5591(2) 0.0268(10) Uani 1 1 d . . . . .
C16 C 0.5701(4) 0.3876(5) 0.3071(2) 0.0261(10) Uani 1 1 d . . . . .
C17 C 0.6803(4) 0.4777(5) 0.3173(2) 0.0255(10) Uani 1 1 d . . . . .
C18 C 0.7327(4) 0.5631(5) 0.2625(2) 0.0285(11) Uani 1 1 d . . . . .
H18 H 0.806152 0.625385 0.271731 0.034 Uiso 1 1 calc R U . . .
C19 C 0.6745(4) 0.5549(5) 0.1934(2) 0.0292(11) Uani 1 1 d . . . . .
H19 H 0.709054 0.613216 0.154427 0.035 Uiso 1 1 calc R U . . .
C20 C 0.5650(4) 0.4626(5) 0.1784(2) 0.0286(11) Uani 1 1 d . . . . .
C21 C 0.5128(4) 0.3790(5) 0.2355(2) 0.0260(10) Uani 1 1 d . . . . .
H21 H 0.439325 0.316678 0.226325 0.031 Uiso 1 1 calc R U . . .
C22 C 0.5076(4) 0.4517(5) 0.1014(2) 0.0363(12) Uani 1 1 d . . . . .
H22A H 0.522044 0.562675 0.075581 0.054 Uiso 1 1 calc R U . . .
H22B H 0.421160 0.433557 0.102416 0.054 Uiso 1 1 calc R U . . .
H22C H 0.541982 0.351712 0.076137 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.368(4) . ?
O1 C9 1.370(5) . ?
O1 C17 1.397(4) . ?
N1 C15 1.364(5) . ?
N1 C8 1.375(5) . ?
N1 C11 1.382(5) . ?
C1 C2 1.375(6) . ?
C1 C6 1.376(6) . ?
N2 C15 1.347(5) . ?
N2 C7 1.379(5) . ?
C2 C3 1.386(6) . ?
C3 C4 1.386(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.409(5) . ?
C6 C7 1.458(5) . ?
C7 C8 1.419(5) . ?
C8 C9 1.416(5) . ?
C9 C10 1.397(5) . ?
C10 C16 1.435(5) . ?
C10 C11 1.445(6) . ?
C11 C12 1.385(6) . ?
C12 C13 1.406(6) . ?
C13 C14 1.397(5) . ?
C14 C15 1.393(6) . ?
C16 C17 1.407(6) . ?
C16 C21 1.412(5) . ?
C17 C18 1.368(6) . ?
C18 C19 1.374(5) . ?
C19 C20 1.416(6) . ?
C20 C21 1.394(6) . ?
C20 C22 1.501(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
C9 O1 C17 104.3(3) . . ?
C15 N1 C8 111.3(3) . . ?
C15 N1 C11 131.0(4) . . ?
C8 N1 C11 117.4(3) . . ?
F1 C1 C2 118.2(4) . . ?
F1 C1 C6 117.9(4) . . ?
C2 C1 C6 123.9(4) . . ?
C15 N2 C7 106.4(3) . . ?
C1 C2 C3 118.7(4) . . ?
C2 C3 C4 119.5(4) . . ?
C5 C4 C3 120.6(4) . . ?
C4 C5 C6 121.0(4) . . ?
C1 C6 C5 116.3(4) . . ?
C1 C6 C7 123.3(4) . . ?
C5 C6 C7 120.4(4) . . ?
N2 C7 C8 110.7(3) . . ?
N2 C7 C6 119.6(4) . . ?
C8 C7 C6 129.6(4) . . ?
N1 C8 C9 101.0(3) . . ?
N1 C8 C7 102.6(4) . . ?
C9 C8 C7 156.0(4) . . ?
O1 C9 C10 112.9(3) . . ?
O1 C9 C8 135.0(4) . . ?
C10 C9 C8 112.0(4) . . ?
C9 C10 C16 105.7(4) . . ?
C9 C10 C11 107.1(4) . . ?
C16 C10 C11 146.7(4) . . ?
N1 C11 C12 113.6(4) . . ?
N1 C11 C10 102.4(3) . . ?
C12 C11 C10 144.0(4) . . ?
C11 C12 C13 118.9(4) . . ?
C14 C13 C12 123.8(4) . . ?
C15 C14 C13 118.3(4) . . ?
N2 C15 N1 109.0(4) . . ?
N2 C15 C14 136.6(4) . . ?
N1 C15 C14 114.3(4) . . ?
C17 C16 C21 117.9(4) . . ?
C17 C16 C10 105.3(3) . . ?
C21 C16 C10 136.8(4) . . ?
C18 C17 O1 124.5(4) . . ?
C18 C17 C16 123.8(4) . . ?
O1 C17 C16 111.8(3) . . ?
C17 C18 C19 117.3(4) . . ?
C18 C19 C20 122.3(4) . . ?
C21 C20 C19 119.2(4) . . ?
C21 C20 C22 120.6(4) . . ?
C19 C20 C22 120.2(4) . . ?
C20 C21 C16 119.5(4) . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.076



####################################################################### 
# 
# 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_DLR88_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2124567'
loop_
_audit_author_name
_audit_author_address
'E Suresh'
;CSIR CSMCRI
India
;
_audit_update_record             
;
2021-11-26 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Cl N3'
_chemical_formula_weight         355.81

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   17.667(2)
_cell_length_b                   13.2247(15)
_cell_length_c                   7.1270(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.212(5)
_cell_angle_gamma                90
_cell_volume                     1648.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3399
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      26.08

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.5633
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'MICRO FOCUS TUBE'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33131
_diffrn_reflns_av_unetI/netI     0.1106
_diffrn_reflns_av_R_equivalents  0.1367
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.954
_reflns_number_total             7145
_reflns_number_gt                4725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.873
_reflns_Friedel_fraction_full    0.909

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0523P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1663 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.46(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7145
_refine_ls_number_parameters     471
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
Cl1_1 Cl 0.43401(8) 1.10930(11) 0.79695(19) 0.0386(4) Uani 1 1 d . . . . .
N1_1 N 0.6478(3) 0.9749(4) 0.6880(6) 0.0239(11) Uani 1 1 d . . . . .
N2_1 N 0.6204(2) 0.8116(3) 0.6993(6) 0.0252(11) Uani 1 1 d . . . . .
N3_1 N 0.7676(3) 1.1853(3) 0.6398(6) 0.0280(11) Uani 1 1 d . . . . .
C1_1 C 0.7432(3) 0.7373(4) 0.6378(7) 0.0241(12) Uani 1 1 d . . . . .
C2_1 C 0.8222(3) 0.7469(4) 0.6514(7) 0.0291(13) Uani 1 1 d . . . . .
H2_1 H 0.845267 0.811237 0.676457 0.035 Uiso 1 1 calc R U . . .
C3_1 C 0.8674(3) 0.6640(4) 0.6288(8) 0.0355(14) Uani 1 1 d . . . . .
H3_1 H 0.921263 0.671475 0.638661 0.043 Uiso 1 1 calc R U . . .
C4_1 C 0.8344(4) 0.5702(4) 0.5921(8) 0.0355(14) Uani 1 1 d . . . . .
H4_1 H 0.865655 0.513225 0.576404 0.043 Uiso 1 1 calc R U . . .
C5_1 C 0.7566(4) 0.5591(4) 0.5781(8) 0.0363(15) Uani 1 1 d . . . . .
H5_1 H 0.733974 0.494593 0.551377 0.044 Uiso 1 1 calc R U . . .
C6_1 C 0.7108(3) 0.6420(4) 0.6030(7) 0.0278(13) Uani 1 1 d . . . . .
H6_1 H 0.657044 0.633594 0.596336 0.033 Uiso 1 1 calc R U . . .
C7_1 C 0.6953(3) 0.8250(4) 0.6636(6) 0.0219(12) Uani 1 1 d . . . . .
C8_1 C 0.7144(3) 0.9287(4) 0.6559(7) 0.0224(12) Uani 1 1 d . . . . .
C9_1 C 0.5922(3) 0.9068(4) 0.7139(7) 0.0252(13) Uani 1 1 d . . . . .
C10_1 C 0.7641(3) 1.0128(4) 0.6305(7) 0.0241(12) Uani 1 1 d . . . . .
C11_1 C 0.7230(3) 1.1012(4) 0.6543(7) 0.0233(12) Uani 1 1 d . . . . .
C12_1 C 0.6475(3) 1.0785(4) 0.6908(7) 0.0236(12) Uani 1 1 d . . . . .
C13_1 C 0.8390(3) 1.0439(4) 0.5970(7) 0.0236(12) Uani 1 1 d . . . . .
C14_1 C 0.8385(3) 1.1510(4) 0.6081(7) 0.0277(13) Uani 1 1 d . . . . .
C15_1 C 0.5227(3) 0.9486(5) 0.7498(7) 0.0288(14) Uani 1 1 d . . . . .
H15_1 H 0.480553 0.907411 0.770101 0.035 Uiso 1 1 calc R U . . .
C16_1 C 0.5790(3) 1.1208(4) 0.7258(8) 0.0258(11) Uani 1 1 d . . . . .
H16_1 H 0.572553 1.192061 0.730684 0.031 Uiso 1 1 calc R U . . .
C17_1 C 0.5189(3) 1.0535(4) 0.7540(7) 0.0266(13) Uani 1 1 d . . . . .
C18_1 C 0.9061(3) 0.9964(4) 0.5576(7) 0.0280(13) Uani 1 1 d . . . . .
H18_1 H 0.908116 0.924890 0.546427 0.034 Uiso 1 1 calc R U . . .
C19_1 C 0.9692(3) 1.0546(5) 0.5353(8) 0.0340(14) Uani 1 1 d . . . . .
H19_1 H 1.014595 1.022282 0.509029 0.041 Uiso 1 1 calc R U . . .
C20_1 C 0.9677(3) 1.1589(5) 0.5506(8) 0.0375(15) Uani 1 1 d . . . . .
H20_1 H 1.012205 1.196600 0.535714 0.045 Uiso 1 1 calc R U . . .
C21_1 C 0.9030(4) 1.2092(5) 0.5868(8) 0.0375(15) Uani 1 1 d . . . . .
H21_1 H 0.902150 1.280849 0.597026 0.045 Uiso 1 1 calc R U . . .
C22_1 C 0.7421(4) 1.2893(4) 0.6376(8) 0.0375(15) Uani 1 1 d . . . . .
H22A_1 H 0.771210 1.325992 0.743588 0.056 Uiso 1 1 calc R U . . .
H22B_1 H 0.687532 1.291221 0.649868 0.056 Uiso 1 1 calc R U . . .
H22C_1 H 0.750104 1.321085 0.517812 0.056 Uiso 1 1 calc R U . . .
Cl1_2 Cl 0.57784(9) 0.55533(11) 0.2030(2) 0.0395(4) Uani 1 1 d . . . . .
N1_2 N 0.3865(2) 0.2586(3) 0.2625(6) 0.0267(11) Uani 1 1 d . . . . .
N2_2 N 0.3572(2) 0.4204(3) 0.2468(6) 0.0247(10) Uani 1 1 d . . . . .
N3_2 N 0.2352(3) 0.6304(3) 0.2733(6) 0.0292(11) Uani 1 1 d . . . . .
C1_2 C 0.2598(3) 0.1843(4) 0.2946(7) 0.0257(12) Uani 1 1 d . . . . .
C2_2 C 0.1810(3) 0.1947(4) 0.2420(7) 0.0294(12) Uani 1 1 d . . . . .
H2_2 H 0.160358 0.257260 0.193386 0.035 Uiso 1 1 calc R U . . .
C3_2 C 0.1331(3) 0.1137(4) 0.2606(8) 0.0368(14) Uani 1 1 d . . . . .
H3_2 H 0.079539 0.120864 0.223059 0.044 Uiso 1 1 calc R U . . .
C4_2 C 0.1620(4) 0.0228(5) 0.3327(8) 0.0383(15) Uani 1 1 d . . . . .
H4_2 H 0.128664 -0.032223 0.346293 0.046 Uiso 1 1 calc R U . . .
C5_2 C 0.2405(4) 0.0123(4) 0.3857(8) 0.0356(15) Uani 1 1 d . . . . .
H5_2 H 0.260865 -0.050313 0.434941 0.043 Uiso 1 1 calc R U . . .
C6_2 C 0.2891(3) 0.0929(4) 0.3667(7) 0.0300(13) Uani 1 1 d . . . . .
H6_2 H 0.342612 0.085314 0.403376 0.036 Uiso 1 1 calc R U . . .
C7_2 C 0.3104(3) 0.2714(4) 0.2785(7) 0.0267(13) Uani 1 1 d . . . . .
C8_2 C 0.4150(3) 0.3520(4) 0.2438(8) 0.0280(13) Uani 1 1 d . . . . .
C9_2 C 0.2901(3) 0.3744(4) 0.2697(7) 0.0260(13) Uani 1 1 d . . . . .
C10_2 C 0.4862(3) 0.3948(4) 0.2267(8) 0.0285(13) Uani 1 1 d . . . . .
H10_2 H 0.530018 0.353972 0.220795 0.034 Uiso 1 1 calc R U . . .
C11_2 C 0.4898(3) 0.4997(4) 0.2187(7) 0.0262(13) Uani 1 1 d . . . . .
C12_2 C 0.4279(3) 0.5661(4) 0.2257(7) 0.0306(13) Uani 1 1 d . . . . .
H12_2 H 0.434606 0.637267 0.219593 0.037 Uiso 1 1 calc R U . . .
C13_2 C 0.3574(3) 0.5249(4) 0.2419(7) 0.0259(13) Uani 1 1 d . . . . .
C14_2 C 0.2382(3) 0.4581(4) 0.2840(7) 0.0250(12) Uani 1 1 d . . . . .
C15_2 C 0.2794(3) 0.5462(4) 0.2650(7) 0.0254(12) Uani 1 1 d . . . . .
C16_2 C 0.1631(3) 0.5970(4) 0.3034(7) 0.0283(13) Uani 1 1 d . . . . .
C17_2 C 0.1624(3) 0.4890(4) 0.3116(7) 0.0259(12) Uani 1 1 d . . . . .
C18_2 C 0.2594(4) 0.7350(4) 0.2669(8) 0.0360(15) Uani 1 1 d . . . . .
H18A_2 H 0.217062 0.775992 0.203795 0.054 Uiso 1 1 calc R U . . .
H18B_2 H 0.302990 0.739669 0.196399 0.054 Uiso 1 1 calc R U . . .
H18C_2 H 0.274499 0.759883 0.396376 0.054 Uiso 1 1 calc R U . . .
C19_2 C 0.0983(3) 0.6542(5) 0.3255(7) 0.0350(14) Uani 1 1 d . . . . .
H19_2 H 0.099032 0.725923 0.320406 0.042 Uiso 1 1 calc R U . . .
C20_2 C 0.0336(3) 0.6027(5) 0.3546(7) 0.0376(15) Uani 1 1 d . . . . .
H20_2 H -0.011447 0.639904 0.366620 0.045 Uiso 1 1 calc R U . . .
C21_2 C 0.0320(3) 0.4977(5) 0.3672(7) 0.0360(14) Uani 1 1 d . . . . .
H21_2 H -0.013640 0.465065 0.390867 0.043 Uiso 1 1 calc R U . . .
C22_2 C 0.0956(3) 0.4398(4) 0.3458(7) 0.0291(13) Uani 1 1 d . . . . .
H22_2 H 0.093846 0.368163 0.354237 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1_1 C17_1 1.738(5) . ?
N1_1 C9_1 1.365(7) . ?
N1_1 C12_1 1.370(7) . ?
N1_1 C8_1 1.373(7) . ?
N2_1 C9_1 1.364(6) . ?
N2_1 C7_1 1.394(7) . ?
N3_1 C11_1 1.376(7) . ?
N3_1 C14_1 1.381(7) . ?
N3_1 C22_1 1.447(7) . ?
C1_1 C2_1 1.391(7) . ?
C1_1 C6_1 1.392(7) . ?
C1_1 C7_1 1.463(7) . ?
C2_1 C3_1 1.379(7) . ?
C3_1 C4_1 1.379(8) . ?
C4_1 C5_1 1.373(8) . ?
C5_1 C6_1 1.389(8) . ?
C7_1 C8_1 1.415(7) . ?
C8_1 C10_1 1.444(8) . ?
C9_1 C15_1 1.402(8) . ?
C10_1 C11_1 1.399(7) . ?
C10_1 C13_1 1.438(7) . ?
C11_1 C12_1 1.426(8) . ?
C12_1 C16_1 1.388(8) . ?
C13_1 C18_1 1.405(8) . ?
C13_1 C14_1 1.419(7) . ?
C14_1 C21_1 1.400(8) . ?
C15_1 C17_1 1.389(7) . ?
C16_1 C17_1 1.423(8) . ?
C18_1 C19_1 1.382(8) . ?
C19_1 C20_1 1.384(8) . ?
C20_1 C21_1 1.379(9) . ?
Cl1_2 C11_2 1.739(5) . ?
N1_2 C8_2 1.348(7) . ?
N1_2 C7_2 1.375(7) . ?
N2_2 C9_2 1.363(7) . ?
N2_2 C8_2 1.367(7) . ?
N2_2 C13_2 1.383(7) . ?
N3_2 C15_2 1.366(7) . ?
N3_2 C16_2 1.393(7) . ?
N3_2 C18_2 1.450(7) . ?
C1_2 C6_2 1.385(7) . ?
C1_2 C2_2 1.395(7) . ?
C1_2 C7_2 1.473(8) . ?
C2_2 C3_2 1.384(7) . ?
C3_2 C4_2 1.376(8) . ?
C4_2 C5_2 1.391(8) . ?
C5_2 C6_2 1.387(8) . ?
C7_2 C9_2 1.407(8) . ?
C8_2 C10_2 1.399(8) . ?
C9_2 C14_2 1.450(8) . ?
C10_2 C11_2 1.390(7) . ?
C11_2 C12_2 1.409(8) . ?
C12_2 C13_2 1.380(8) . ?
C13_2 C15_2 1.439(8) . ?
C14_2 C15_2 1.390(7) . ?
C14_2 C17_2 1.440(7) . ?
C16_2 C19_2 1.400(8) . ?
C16_2 C17_2 1.431(8) . ?
C17_2 C22_2 1.400(7) . ?
C19_2 C20_2 1.370(8) . ?
C20_2 C21_2 1.393(8) . ?
C21_2 C22_2 1.386(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9_1 N1_1 C12_1 130.8(5) . . ?
C9_1 N1_1 C8_1 112.3(4) . . ?
C12_1 N1_1 C8_1 116.9(5) . . ?
C9_1 N2_1 C7_1 105.2(4) . . ?
C11_1 N3_1 C14_1 106.9(4) . . ?
C11_1 N3_1 C22_1 126.0(5) . . ?
C14_1 N3_1 C22_1 126.8(5) . . ?
C2_1 C1_1 C6_1 118.5(5) . . ?
C2_1 C1_1 C7_1 120.8(5) . . ?
C6_1 C1_1 C7_1 120.6(5) . . ?
C3_1 C2_1 C1_1 120.8(5) . . ?
C4_1 C3_1 C2_1 120.1(6) . . ?
C5_1 C4_1 C3_1 120.1(6) . . ?
C4_1 C5_1 C6_1 120.2(6) . . ?
C5_1 C6_1 C1_1 120.3(6) . . ?
N2_1 C7_1 C8_1 111.6(5) . . ?
N2_1 C7_1 C1_1 120.2(5) . . ?
C8_1 C7_1 C1_1 128.2(5) . . ?
N1_1 C8_1 C7_1 102.2(4) . . ?
N1_1 C8_1 C10_1 103.2(5) . . ?
C7_1 C8_1 C10_1 154.6(5) . . ?
N2_1 C9_1 N1_1 108.7(5) . . ?
N2_1 C9_1 C15_1 135.7(5) . . ?
N1_1 C9_1 C15_1 115.5(5) . . ?
C11_1 C10_1 C13_1 106.7(5) . . ?
C11_1 C10_1 C8_1 107.0(5) . . ?
C13_1 C10_1 C8_1 146.2(5) . . ?
N3_1 C11_1 C10_1 110.7(5) . . ?
N3_1 C11_1 C12_1 138.1(5) . . ?
C10_1 C11_1 C12_1 111.2(5) . . ?
N1_1 C12_1 C16_1 114.3(5) . . ?
N1_1 C12_1 C11_1 101.6(4) . . ?
C16_1 C12_1 C11_1 144.1(5) . . ?
C18_1 C13_1 C14_1 117.9(5) . . ?
C18_1 C13_1 C10_1 136.8(5) . . ?
C14_1 C13_1 C10_1 105.3(5) . . ?
N3_1 C14_1 C21_1 127.4(5) . . ?
N3_1 C14_1 C13_1 110.4(5) . . ?
C21_1 C14_1 C13_1 122.1(5) . . ?
C17_1 C15_1 C9_1 116.3(5) . . ?
C12_1 C16_1 C17_1 117.4(5) . . ?
C15_1 C17_1 C16_1 125.7(5) . . ?
C15_1 C17_1 Cl1_1 118.3(4) . . ?
C16_1 C17_1 Cl1_1 116.1(4) . . ?
C19_1 C18_1 C13_1 119.5(5) . . ?
C18_1 C19_1 C20_1 121.3(6) . . ?
C21_1 C20_1 C19_1 121.5(5) . . ?
C20_1 C21_1 C14_1 117.6(5) . . ?
C8_2 N1_2 C7_2 106.2(4) . . ?
C9_2 N2_2 C8_2 111.8(5) . . ?
C9_2 N2_2 C13_2 117.1(5) . . ?
C8_2 N2_2 C13_2 131.0(5) . . ?
C15_2 N3_2 C16_2 106.8(5) . . ?
C15_2 N3_2 C18_2 127.1(5) . . ?
C16_2 N3_2 C18_2 125.9(5) . . ?
C6_2 C1_2 C2_2 119.4(5) . . ?
C6_2 C1_2 C7_2 120.8(5) . . ?
C2_2 C1_2 C7_2 119.7(5) . . ?
C3_2 C2_2 C1_2 120.0(5) . . ?
C4_2 C3_2 C2_2 120.8(6) . . ?
C3_2 C4_2 C5_2 119.4(6) . . ?
C6_2 C5_2 C4_2 120.2(6) . . ?
C1_2 C6_2 C5_2 120.2(6) . . ?
N1_2 C7_2 C9_2 111.2(5) . . ?
N1_2 C7_2 C1_2 121.5(5) . . ?
C9_2 C7_2 C1_2 127.3(5) . . ?
N1_2 C8_2 N2_2 108.3(5) . . ?
N1_2 C8_2 C10_2 137.1(5) . . ?
N2_2 C8_2 C10_2 114.6(5) . . ?
N2_2 C9_2 C7_2 102.5(5) . . ?
N2_2 C9_2 C14_2 103.7(5) . . ?
C7_2 C9_2 C14_2 153.6(5) . . ?
C11_2 C10_2 C8_2 117.0(5) . . ?
C10_2 C11_2 C12_2 125.5(5) . . ?
C10_2 C11_2 Cl1_2 118.2(4) . . ?
C12_2 C11_2 Cl1_2 116.4(4) . . ?
C13_2 C12_2 C11_2 118.1(5) . . ?
C12_2 C13_2 N2_2 113.7(5) . . ?
C12_2 C13_2 C15_2 145.5(5) . . ?
N2_2 C13_2 C15_2 100.7(4) . . ?
C15_2 C14_2 C17_2 106.6(5) . . ?
C15_2 C14_2 C9_2 106.8(5) . . ?
C17_2 C14_2 C9_2 146.7(5) . . ?
N3_2 C15_2 C14_2 111.6(5) . . ?
N3_2 C15_2 C13_2 136.6(5) . . ?
C14_2 C15_2 C13_2 111.8(5) . . ?
N3_2 C16_2 C19_2 128.9(5) . . ?
N3_2 C16_2 C17_2 109.6(5) . . ?
C19_2 C16_2 C17_2 121.5(5) . . ?
C22_2 C17_2 C16_2 118.9(5) . . ?
C22_2 C17_2 C14_2 135.8(5) . . ?
C16_2 C17_2 C14_2 105.3(5) . . ?
C20_2 C19_2 C16_2 117.6(6) . . ?
C19_2 C20_2 C21_2 122.0(6) . . ?
C22_2 C21_2 C20_2 121.3(6) . . ?
C21_2 C22_2 C17_2 118.7(6) . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.067



