# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_AB_B2_0001
_database_code_depnum_ccdc_archive 'CCDC 2237386'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2023-01-20 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Helen Boffey'
_cambridge_user_crsid            hkb32
_cambridge_supervisor_name       'Steve Andrews'
_cambridge_supervisor_crsid      spa26
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             ARUK2000020-001
_cambridge_data_id               AB_B2_0001
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 F3 N6 O2 +, Cl -'
_chemical_formula_sum            'C17 H18 Cl F3 N6 O2'
_chemical_formula_weight         430.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.6397(2)
_cell_length_b                   10.0511(3)
_cell_length_c                   28.1099(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.840(2)
_cell_angle_gamma                90
_cell_volume                     1871.74(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      66.83

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    2.334
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17933
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         66.847
_diffrn_reflns_theta_full        66.847
_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             3304
_reflns_number_gt                2845
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0428P)²+1.0209P] 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         3304
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058

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 0.16457(6) 0.81874(4) 0.60206(2) 0.02573(13) Uani 1 1 d . . . . .
F1 F 0.1569(2) -0.37323(16) 0.25584(5) 0.0586(4) Uani 1 1 d . . . . .
F2 F 0.1700(2) -0.23909(16) 0.19790(5) 0.0568(4) Uani 1 1 d . . . . .
F3 F 0.36476(18) -0.40743(13) 0.20188(5) 0.0446(3) Uani 1 1 d . . . . .
O1 O 0.2605(2) -0.16074(14) 0.39608(5) 0.0338(3) Uani 1 1 d . . . . .
O2 O 0.2666(2) 0.52289(13) 0.48612(4) 0.0300(3) Uani 1 1 d . . . . .
N1 N 0.4908(2) -0.02277(15) 0.36480(5) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.3088(2) 0.27448(17) 0.45576(5) 0.0240(3) Uani 1 1 d . . . . .
N3 N 0.2535(2) 0.11152(15) 0.51358(5) 0.0213(3) Uani 1 1 d . . . . .
N4 N 0.2424(2) -0.10773(16) 0.49334(6) 0.0242(3) Uani 1 1 d . . . . .
N5 N 0.2488(2) 0.33257(15) 0.53364(5) 0.0232(3) Uani 1 1 d . . . . .
N6 N 0.2266(3) 0.52918(17) 0.56689(6) 0.0321(4) Uani 1 1 d . . . . .
C1 C 0.5335(3) -0.09458(17) 0.32343(6) 0.0199(4) Uani 1 1 d . . . . .
C2 C 0.3912(3) -0.17358(18) 0.29855(6) 0.0211(4) Uani 1 1 d . . . . .
H2A H 0.2616 -0.1867 0.3101 0.025 Uiso 1 1 calc R U . . .
C3 C 0.4417(3) -0.23319(17) 0.25634(6) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.6303(3) -0.21591(19) 0.23856(6) 0.0274(4) Uani 1 1 d . . . . .
H4A H 0.6622 -0.2569 0.2095 0.033 Uiso 1 1 calc R U . . .
C5 C 0.7705(3) -0.1374(2) 0.26422(7) 0.0317(4) Uani 1 1 d . . . . .
H5A H 0.9003 -0.1245 0.2527 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7240(3) -0.07780(19) 0.30636(7) 0.0269(4) Uani 1 1 d . . . . .
H6A H 0.8223 -0.0252 0.3238 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2859(3) -0.3140(2) 0.22865(7) 0.0295(4) Uani 1 1 d . . . . .
C8 C 0.3537(3) -0.05465(18) 0.39624(6) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.3238(2) 0.04966(18) 0.43265(6) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.3367(3) 0.18113(19) 0.42220(6) 0.0229(4) Uani 1 1 d . . . . .
H10A H 0.3656 0.2078 0.3910 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2705(2) 0.23616(18) 0.50055(6) 0.0203(4) Uani 1 1 d . . . . .
C12 C 0.2706(2) 0.01630(18) 0.47995(6) 0.0196(4) Uani 1 1 d . . . . .
C13 C 0.2489(3) 0.47093(18) 0.52536(6) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.2215(4) 0.30078(19) 0.58378(7) 0.0324(5) Uani 1 1 d . . . . .
H14A H 0.3385 0.2505 0.5982 0.039 Uiso 1 1 calc R U . . .
H14B H 0.0972 0.2480 0.5869 0.039 Uiso 1 1 calc R U . . .
C15 C 0.2050(3) 0.43922(18) 0.60738(6) 0.0251(4) Uani 1 1 d . . . . .
C16 C -0.0008(3) 0.4585(2) 0.62703(8) 0.0397(5) Uani 1 1 d . . . . .
H16A H -0.0142 0.3982 0.6540 0.059 Uiso 1 1 calc R U . . .
H16B H -0.0141 0.5507 0.6377 0.059 Uiso 1 1 calc R U . . .
H16C H -0.1067 0.4390 0.6020 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3742(4) 0.4645(2) 0.64518(9) 0.0457(6) Uani 1 1 d . . . . .
H17A H 0.3596 0.4044 0.6722 0.069 Uiso 1 1 calc R U . . .
H17B H 0.5044 0.4485 0.6317 0.069 Uiso 1 1 calc R U . . .
H17C H 0.3679 0.5569 0.6561 0.069 Uiso 1 1 calc R U . . .
H6 H 0.215(3) 0.614(3) 0.5704(8) 0.033(6) Uiso 1 1 d . . . . .
H1 H 0.577(3) 0.036(2) 0.3724(8) 0.032(6) Uiso 1 1 d . . . . .
H41 H 0.239(3) -0.169(2) 0.4727(9) 0.034(6) Uiso 1 1 d . . . . .
H2 H 0.312(3) 0.356(3) 0.4504(8) 0.035(6) Uiso 1 1 d . . . . .
H42 H 0.209(3) -0.128(2) 0.5225(9) 0.035(6) Uiso 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
F1 C7 1.327(2) . ?
F2 C7 1.349(2) . ?
F3 C7 1.332(2) . ?
O1 C8 1.233(2) . ?
O2 C13 1.233(2) . ?
N1 C8 1.349(2) . ?
N1 C1 1.414(2) . ?
N1 H1 0.84(2) . ?
N2 C10 1.352(2) . ?
N2 C11 1.357(2) . ?
N2 H2 0.83(3) . ?
N3 C11 1.312(2) . ?
N3 C12 1.355(2) . ?
N4 C12 1.319(2) . ?
N4 H41 0.85(3) . ?
N4 H42 0.89(3) . ?
N5 C11 1.358(2) . ?
N5 C13 1.410(2) . ?
N5 C14 1.468(2) . ?
N6 C13 1.323(2) . ?
N6 C15 1.468(2) . ?
N6 H6 0.86(2) . ?
C1 C2 1.387(2) . ?
C1 C6 1.393(3) . ?
C2 C3 1.390(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C7 1.493(3) . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C9 1.488(2) . ?
C9 C10 1.358(3) . ?
C9 C12 1.438(2) . ?
C10 H10A 0.9500 . ?
C14 C15 1.548(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.515(3) . ?
C15 C16 1.520(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 126.80(16) . . ?
C8 N1 H1 118.6(15) . . ?
C1 N1 H1 113.4(16) . . ?
C10 N2 C11 119.56(17) . . ?
C10 N2 H2 123.2(16) . . ?
C11 N2 H2 117.3(16) . . ?
C11 N3 C12 117.82(15) . . ?
C12 N4 H41 119.3(16) . . ?
C12 N4 H42 121.9(15) . . ?
H41 N4 H42 118(2) . . ?
C11 N5 C13 126.14(15) . . ?
C11 N5 C14 121.87(15) . . ?
C13 N5 C14 111.99(14) . . ?
C13 N6 C15 115.72(16) . . ?
C13 N6 H6 123.8(15) . . ?
C15 N6 H6 120.3(15) . . ?
C2 C1 C6 119.96(16) . . ?
C2 C1 N1 122.66(16) . . ?
C6 C1 N1 117.29(16) . . ?
C1 C2 C3 118.82(16) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 121.86(17) . . ?
C4 C3 C7 119.34(16) . . ?
C2 C3 C7 118.77(16) . . ?
C5 C4 C3 118.30(17) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
C6 C5 C4 120.84(18) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C1 120.21(17) . . ?
C5 C6 H6A 119.9 . . ?
C1 C6 H6A 119.9 . . ?
F1 C7 F3 107.62(17) . . ?
F1 C7 F2 104.87(17) . . ?
F3 C7 F2 105.11(15) . . ?
F1 C7 C3 113.29(16) . . ?
F3 C7 C3 113.17(16) . . ?
F2 C7 C3 112.10(17) . . ?
O1 C8 N1 124.30(16) . . ?
O1 C8 C9 121.48(16) . . ?
N1 C8 C9 114.22(15) . . ?
C10 C9 C12 116.74(16) . . ?
C10 C9 C8 121.59(16) . . ?
C12 C9 C8 121.61(16) . . ?
N2 C10 C9 120.73(16) . . ?
N2 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
N3 C11 N2 123.71(16) . . ?
N3 C11 N5 118.37(16) . . ?
N2 C11 N5 117.92(16) . . ?
N4 C12 N3 116.63(16) . . ?
N4 C12 C9 122.17(16) . . ?
N3 C12 C9 121.16(16) . . ?
O2 C13 N6 128.67(18) . . ?
O2 C13 N5 124.50(16) . . ?
N6 C13 N5 106.84(16) . . ?
N5 C14 C15 103.44(15) . . ?
N5 C14 H14A 111.1 . . ?
C15 C14 H14A 111.1 . . ?
N5 C14 H14B 111.1 . . ?
C15 C14 H14B 111.1 . . ?
H14A C14 H14B 109.0 . . ?
N6 C15 C17 109.53(17) . . ?
N6 C15 C16 109.88(16) . . ?
C17 C15 C16 111.47(18) . . ?
N6 C15 C14 102.01(14) . . ?
C17 C15 C14 112.37(17) . . ?
C16 C15 C14 111.17(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 27.9(3) . . . . ?
C8 N1 C1 C6 -155.58(17) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
N1 C1 C2 C3 175.49(16) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C1 C2 C3 C7 -177.73(16) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C7 C3 C4 C5 178.23(18) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N1 C1 C6 C5 -175.32(17) . . . . ?
C4 C3 C7 F1 151.21(18) . . . . ?
C2 C3 C7 F1 -30.9(2) . . . . ?
C4 C3 C7 F3 28.3(3) . . . . ?
C2 C3 C7 F3 -153.79(17) . . . . ?
C4 C3 C7 F2 -90.3(2) . . . . ?
C2 C3 C7 F2 87.5(2) . . . . ?
C1 N1 C8 O1 8.6(3) . . . . ?
C1 N1 C8 C9 -172.19(15) . . . . ?
O1 C8 C9 C10 -146.62(18) . . . . ?
N1 C8 C9 C10 34.2(2) . . . . ?
O1 C8 C9 C12 30.4(3) . . . . ?
N1 C8 C9 C12 -148.77(16) . . . . ?
C11 N2 C10 C9 1.0(3) . . . . ?
C12 C9 C10 N2 2.7(2) . . . . ?
C8 C9 C10 N2 179.91(16) . . . . ?
C12 N3 C11 N2 -1.6(2) . . . . ?
C12 N3 C11 N5 178.43(15) . . . . ?
C10 N2 C11 N3 -1.8(3) . . . . ?
C10 N2 C11 N5 178.25(16) . . . . ?
C13 N5 C11 N3 -175.52(16) . . . . ?
C14 N5 C11 N3 4.4(3) . . . . ?
C13 N5 C11 N2 4.5(3) . . . . ?
C14 N5 C11 N2 -175.58(17) . . . . ?
C11 N3 C12 N4 -176.55(15) . . . . ?
C11 N3 C12 C9 5.5(2) . . . . ?
C10 C9 C12 N4 176.07(16) . . . . ?
C8 C9 C12 N4 -1.1(3) . . . . ?
C10 C9 C12 N3 -6.1(2) . . . . ?
C8 C9 C12 N3 176.71(15) . . . . ?
C15 N6 C13 O2 178.74(19) . . . . ?
C15 N6 C13 N5 -1.2(2) . . . . ?
C11 N5 C13 O2 1.0(3) . . . . ?
C14 N5 C13 O2 -178.99(18) . . . . ?
C11 N5 C13 N6 -179.12(17) . . . . ?
C14 N5 C13 N6 0.9(2) . . . . ?
C11 N5 C14 C15 179.69(16) . . . . ?
C13 N5 C14 C15 -0.4(2) . . . . ?
C13 N6 C15 C17 120.2(2) . . . . ?
C13 N6 C15 C16 -117.07(19) . . . . ?
C13 N6 C15 C14 0.9(2) . . . . ?
N5 C14 C15 N6 -0.3(2) . . . . ?
N5 C14 C15 C17 -117.49(19) . . . . ?
N5 C14 C15 C16 116.79(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.84(2) 2.33(2) 3.1662(16) 174(2) 3_666
N2 H2 O2 0.83(3) 1.99(2) 2.660(2) 137(2) .
N4 H41 O1 0.85(3) 2.17(2) 2.796(2) 131(2) .
N4 H42 Cl1 0.89(3) 2.34(3) 3.2195(17) 173(2) 1_545
N6 H6 Cl1 0.86(2) 2.28(3) 3.1101(17) 163(2) .

####################################################################### 
# 
# 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_AB_B1_0015
_database_code_depnum_ccdc_archive 'CCDC 2237387'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2023-01-20 deposited with the CCDC.	2023-04-04 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2014/7

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Simon Edwards'
_cambridge_user_crsid            sde30
_cambridge_supervisor_name       ?
_cambridge_supervisor_crsid      ?
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid 'Andrew Bond'
_cambridge_sample_id             ARUK2001750-002
_cambridge_data_id               AB_B1_0015
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Cl2 N5 O'
_chemical_formula_sum            'C19 H15 Cl2 N5 O'
_chemical_formula_weight         400.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   11.3629(3)
_cell_length_b                   7.1919(2)
_cell_length_c                   22.2901(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.2056(12)
_cell_angle_gamma                90
_cell_volume                     1786.84(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      70.32

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.440
_shelx_estimated_absorpt_T_min   0.518
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5978
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30283
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.966
_diffrn_reflns_theta_max         70.316
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3416
_reflns_number_gt                3037
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0360P)²+0.8398P] 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         3416
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.054

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 0.19313(3) -0.06817(5) 0.69409(2) 0.02898(11) Uani 1 1 d . . . . .
Cl2 Cl 0.98297(4) 1.58852(7) 0.61669(2) 0.04412(14) Uani 1 1 d . . . . .
O1 O 0.14527(11) -0.12669(17) 0.56274(5) 0.0338(3) Uani 1 1 d . . . . .
N1 N 0.43594(12) 0.65550(18) 0.55810(6) 0.0244(3) Uani 1 1 d . . . . .
C2 C 0.50959(15) 0.7739(2) 0.53629(7) 0.0268(3) Uani 1 1 d . . . . .
H2A H 0.5146 0.7558 0.4946 0.032 Uiso 1 1 calc R U . . .
N3 N 0.57597(12) 0.91156(19) 0.56426(6) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.55934(13) 0.9311(2) 0.62222(6) 0.0191(3) Uani 1 1 d . . . . .
C5 C 0.48549(12) 0.8232(2) 0.65164(6) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.42365(12) 0.6759(2) 0.61639(6) 0.0193(3) Uani 1 1 d . . . . .
C7 C 0.50318(13) 0.8959(2) 0.71174(7) 0.0214(3) Uani 1 1 d . . . . .
H7A H 0.4641 0.8510 0.7429 0.026 Uiso 1 1 calc R U . . .
N8 N 0.58105(11) 1.03446(18) 0.71896(5) 0.0215(3) Uani 1 1 d . . . . .
N9 N 0.61496(11) 1.05697(17) 0.66348(5) 0.0200(3) Uani 1 1 d . . . . .
N10 N 0.35750(12) 0.55396(18) 0.64202(6) 0.0223(3) Uani 1 1 d . . . . .
H10 H 0.3592(16) 0.572(3) 0.6794(9) 0.028(5) Uiso 1 1 d . . . . .
C11 C 0.30237(13) 0.3867(2) 0.61758(7) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.27587(13) 0.2566(2) 0.65946(7) 0.0212(3) Uani 1 1 d . . . . .
H12A H 0.2944 0.2837 0.7020 0.025 Uiso 1 1 calc R U . . .
C13 C 0.22307(13) 0.0894(2) 0.63975(7) 0.0212(3) Uani 1 1 d . . . . .
C14 C 0.19551(13) 0.0432(2) 0.57765(7) 0.0248(3) Uani 1 1 d . . . . .
C15 C 0.22090(15) 0.1742(2) 0.53634(7) 0.0307(4) Uani 1 1 d . . . . .
H15A H 0.2026 0.1467 0.4939 0.037 Uiso 1 1 calc R U . . .
C16 C 0.27257(15) 0.3450(2) 0.55556(7) 0.0286(3) Uani 1 1 d . . . . .
H16A H 0.2875 0.4332 0.5262 0.034 Uiso 1 1 calc R U . . .
C17 C 0.12961(17) -0.1815(3) 0.49990(8) 0.0369(4) Uani 1 1 d . . . . .
H17A H 0.0965 -0.3076 0.4951 0.055 Uiso 1 1 calc R U . . .
H17B H 0.2073 -0.1791 0.4870 0.055 Uiso 1 1 calc R U . . .
H17C H 0.0743 -0.0953 0.4746 0.055 Uiso 1 1 calc R U . . .
C18 C 0.70493(13) 1.1887(2) 0.65504(6) 0.0197(3) Uani 1 1 d . . . . .
C19 C 0.66916(14) 1.3530(2) 0.62496(7) 0.0256(3) Uani 1 1 d . . . . .
H19A H 0.5862 1.3794 0.6119 0.031 Uiso 1 1 calc R U . . .
C20 C 0.75454(15) 1.4798(2) 0.61372(7) 0.0298(4) Uani 1 1 d . . . . .
H20A H 0.7311 1.5941 0.5936 0.036 Uiso 1 1 calc R U . . .
C21 C 0.87437(15) 1.4355(2) 0.63259(7) 0.0282(3) Uani 1 1 d . . . . .
C22 C 0.91032(14) 1.2716(2) 0.66282(7) 0.0283(3) Uani 1 1 d . . . . .
H22A H 0.9934 1.2455 0.6754 0.034 Uiso 1 1 calc R U . . .
C23 C 0.82559(14) 1.1440(2) 0.67507(7) 0.0241(3) Uani 1 1 d . . . . .
C24 C 0.86337(16) 0.9665(3) 0.70892(9) 0.0390(4) Uani 1 1 d . . . . .
H24A H 0.9466 0.9379 0.7064 0.058 Uiso 1 1 calc R U . . .
H24B H 0.8111 0.8648 0.6906 0.058 Uiso 1 1 calc R U . . .
H24C H 0.8571 0.9808 0.7519 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.7400(15) . ?
Cl2 C21 1.7405(16) . ?
O1 C14 1.3621(19) . ?
O1 C17 1.433(2) . ?
N1 C6 1.3415(19) . ?
N1 C2 1.349(2) . ?
C2 N3 1.325(2) . ?
C2 H2A 0.9500 . ?
N3 C4 1.3489(19) . ?
C4 N9 1.3562(19) . ?
C4 C5 1.397(2) . ?
C5 C7 1.416(2) . ?
C5 C6 1.421(2) . ?
C6 N10 1.3515(19) . ?
C7 N8 1.3213(19) . ?
C7 H7A 0.9500 . ?
N8 N9 1.3744(17) . ?
N9 C18 1.4329(18) . ?
N10 C11 1.4153(19) . ?
N10 H10 0.84(2) . ?
C11 C16 1.391(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.377(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.399(2) . ?
C14 C15 1.386(2) . ?
C15 C16 1.393(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.380(2) . ?
C18 C23 1.395(2) . ?
C19 C20 1.389(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.382(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.379(2) . ?
C22 C23 1.395(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.502(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O1 C17 116.87(13) . . ?
C6 N1 C2 117.96(13) . . ?
N3 C2 N1 129.67(14) . . ?
N3 C2 H2A 115.2 . . ?
N1 C2 H2A 115.2 . . ?
C2 N3 C4 110.83(13) . . ?
N3 C4 N9 125.83(13) . . ?
N3 C4 C5 126.92(14) . . ?
N9 C4 C5 107.21(12) . . ?
C4 C5 C7 104.54(13) . . ?
C4 C5 C6 115.62(13) . . ?
C7 C5 C6 139.73(14) . . ?
N1 C6 N10 120.64(13) . . ?
N1 C6 C5 118.92(13) . . ?
N10 C6 C5 120.38(13) . . ?
N8 C7 C5 111.26(13) . . ?
N8 C7 H7A 124.4 . . ?
C5 C7 H7A 124.4 . . ?
C7 N8 N9 106.11(12) . . ?
C4 N9 N8 110.87(11) . . ?
C4 N9 C18 127.07(12) . . ?
N8 N9 C18 121.87(11) . . ?
C6 N10 C11 129.01(13) . . ?
C6 N10 H10 114.2(13) . . ?
C11 N10 H10 116.0(13) . . ?
C16 C11 C12 118.55(14) . . ?
C16 C11 N10 124.76(14) . . ?
C12 C11 N10 116.70(13) . . ?
C13 C12 C11 120.62(14) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 121.55(14) . . ?
C12 C13 Cl1 118.60(11) . . ?
C14 C13 Cl1 119.83(12) . . ?
O1 C14 C15 125.38(14) . . ?
O1 C14 C13 117.21(14) . . ?
C15 C14 C13 117.41(14) . . ?
C14 C15 C16 121.65(15) . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C11 C16 C15 120.19(15) . . ?
C11 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
O1 C17 H17A 109.5 . . ?
O1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 122.11(14) . . ?
C19 C18 N9 118.66(13) . . ?
C23 C18 N9 119.18(13) . . ?
C18 C19 C20 119.96(15) . . ?
C18 C19 H19A 120.0 . . ?
C20 C19 H19A 120.0 . . ?
C21 C20 C19 118.36(15) . . ?
C21 C20 H20A 120.8 . . ?
C19 C20 H20A 120.8 . . ?
C22 C21 C20 121.76(15) . . ?
C22 C21 Cl2 119.03(13) . . ?
C20 C21 Cl2 119.20(13) . . ?
C21 C22 C23 120.52(15) . . ?
C21 C22 H22A 119.7 . . ?
C23 C22 H22A 119.7 . . ?
C18 C23 C22 117.28(15) . . ?
C18 C23 C24 121.60(14) . . ?
C22 C23 C24 121.12(15) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 N3 1.0(3) . . . . ?
N1 C2 N3 C4 -2.4(2) . . . . ?
C2 N3 C4 N9 178.97(14) . . . . ?
C2 N3 C4 C5 1.2(2) . . . . ?
N3 C4 C5 C7 178.05(15) . . . . ?
N9 C4 C5 C7 -0.06(16) . . . . ?
N3 C4 C5 C6 1.2(2) . . . . ?
N9 C4 C5 C6 -176.94(12) . . . . ?
C2 N1 C6 N10 -175.56(14) . . . . ?
C2 N1 C6 C5 1.8(2) . . . . ?
C4 C5 C6 N1 -2.7(2) . . . . ?
C7 C5 C6 N1 -178.01(17) . . . . ?
C4 C5 C6 N10 174.67(13) . . . . ?
C7 C5 C6 N10 -0.7(3) . . . . ?
C4 C5 C7 N8 -0.43(17) . . . . ?
C6 C5 C7 N8 175.21(17) . . . . ?
C5 C7 N8 N9 0.74(16) . . . . ?
N3 C4 N9 N8 -177.62(14) . . . . ?
C5 C4 N9 N8 0.51(16) . . . . ?
N3 C4 N9 C18 -2.6(2) . . . . ?
C5 C4 N9 C18 175.58(13) . . . . ?
C7 N8 N9 C4 -0.78(16) . . . . ?
C7 N8 N9 C18 -176.15(13) . . . . ?
N1 C6 N10 C11 6.1(2) . . . . ?
C5 C6 N10 C11 -171.19(14) . . . . ?
C6 N10 C11 C16 -22.2(2) . . . . ?
C6 N10 C11 C12 158.30(15) . . . . ?
C16 C11 C12 C13 1.0(2) . . . . ?
N10 C11 C12 C13 -179.48(13) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C12 C13 Cl1 179.51(11) . . . . ?
C17 O1 C14 C15 7.1(2) . . . . ?
C17 O1 C14 C13 -173.25(15) . . . . ?
C12 C13 C14 O1 178.91(14) . . . . ?
Cl1 C13 C14 O1 0.1(2) . . . . ?
C12 C13 C14 C15 -1.4(2) . . . . ?
Cl1 C13 C14 C15 179.80(12) . . . . ?
O1 C14 C15 C16 -179.96(16) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C12 C11 C16 C15 -2.0(2) . . . . ?
N10 C11 C16 C15 178.53(15) . . . . ?
C14 C15 C16 C11 1.3(3) . . . . ?
C4 N9 C18 C19 81.68(19) . . . . ?
N8 N9 C18 C19 -103.75(16) . . . . ?
C4 N9 C18 C23 -95.67(18) . . . . ?
N8 N9 C18 C23 78.91(18) . . . . ?
C23 C18 C19 C20 0.1(2) . . . . ?
N9 C18 C19 C20 -177.18(14) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C20 C21 C22 -1.1(2) . . . . ?
C19 C20 C21 Cl2 177.81(12) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
Cl2 C21 C22 C23 -178.56(12) . . . . ?
C19 C18 C23 C22 -0.8(2) . . . . ?
N9 C18 C23 C22 176.43(13) . . . . ?
C19 C18 C23 C24 178.71(16) . . . . ?
N9 C18 C23 C24 -4.0(2) . . . . ?
C21 C22 C23 C18 0.6(2) . . . . ?
C21 C22 C23 C24 -178.92(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 N8 0.84(2) 2.25(2) 3.0445(18) 157.4(17) 2_646

