# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc2hp62h
_database_code_depnum_ccdc_archive 'CCDC 2314276'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2024-5l0dx 2024
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_audit_creation_date             2023-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2 O3'
_chemical_formula_sum            'C22 H16 N2 O3'
_chemical_formula_weight         356.37
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3985(3)
_cell_length_b                   11.1440(6)
_cell_length_c                   24.0417(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1714.29(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4717
_cell_measurement_temperature    125
_cell_measurement_theta_max      74.0000
_cell_measurement_theta_min      4.3590
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.757
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9455
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.390
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_temperature      125
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   0.50    5.00    --  -25.00  26.00-144.00  360
  2  ω   -193.00 -13.00   0.50   10.00    -- -103.00  33.00-108.00  360
  3  ω   -192.50 -19.00   0.50   10.00    -- -103.00  20.00   0.00  347
  4  ω   -193.00 -29.00   0.50   10.00    -- -103.00  53.00 -72.00  328
  5  ω   -193.00 -92.00   0.50   10.00    -- -103.00  53.00 108.00  202
;
_diffrn_measurement_device       'AFC11: Quarter χ 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0919871000
_diffrn_orient_matrix_UB_12      0.1248737000
_diffrn_orient_matrix_UB_13      0.0125162000
_diffrn_orient_matrix_UB_21      -0.1229766000
_diffrn_orient_matrix_UB_22      0.0528434000
_diffrn_orient_matrix_UB_23      -0.0493910000
_diffrn_orient_matrix_UB_31      -0.1853516000
_diffrn_orient_matrix_UB_32      0.0268619000
_diffrn_orient_matrix_UB_33      0.0388933000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2542
_reflns_number_total             3412
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 835 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
O2 O 0.9395(4) 0.3790(2) 0.36497(12) 0.0432(7) Uani 1 1 d . . . . .
O6 O 0.9254(5) 0.2970(3) 0.24488(12) 0.0504(8) Uani 1 1 d . . . . .
O7 O 1.0709(6) 0.1110(3) 0.23001(15) 0.0685(11) Uani 1 1 d . . . . .
N3 N 0.6156(5) 0.4552(3) 0.33640(12) 0.0334(7) Uani 1 1 d . . . . .
N4 N 0.4833(5) 0.4422(3) 0.28997(12) 0.0370(8) Uani 1 1 d . . . . .
C1 C 0.7497(7) 0.3031(4) 0.28313(15) 0.0385(9) Uani 1 1 d . . . . .
C2 C 0.7895(6) 0.3822(4) 0.33391(15) 0.0354(9) Uani 1 1 d . . . . .
C5 C 0.5563(7) 0.3590(4) 0.25916(15) 0.0406(10) Uani 1 1 d . . . . .
C7 C 0.9406(8) 0.1732(4) 0.25140(17) 0.0517(11) Uani 1 1 d . . . . .
C8 C 0.7609(7) 0.1636(3) 0.29051(16) 0.0402(10) Uani 1 1 d . . . . .
H8 H 0.639271 0.124104 0.271891 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8012(6) 0.1072(3) 0.34695(17) 0.0377(9) Uani 1 1 d . . . . .
C10 C 0.6545(7) 0.1242(4) 0.39152(15) 0.0382(9) Uani 1 1 d . . . . .
C11 C 0.4664(6) 0.1902(4) 0.38504(16) 0.0396(9) Uani 1 1 d . . . . .
H11 H 0.433145 0.223175 0.349684 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3323(7) 0.2075(4) 0.42847(17) 0.0462(10) Uani 1 1 d . . . . .
H12 H 0.207925 0.252761 0.423355 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3791(8) 0.1581(4) 0.48082(18) 0.0518(12) Uani 1 1 d . . . . .
H13 H 0.287123 0.171492 0.511201 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5555(8) 0.0909(4) 0.48849(17) 0.0498(12) Uani 1 1 d . . . . .
H14 H 0.582846 0.056118 0.523826 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6967(7) 0.0728(4) 0.44450(17) 0.0419(10) Uani 1 1 d . . . . .
C16 C 0.8831(8) 0.0066(4) 0.4515(2) 0.0504(11) Uani 1 1 d . . . . .
H16 H 0.914881 -0.026065 0.486971 0.061 Uiso 1 1 calc R U . . .
C17 C 1.0185(8) -0.0116(4) 0.4085(2) 0.0536(12) Uani 1 1 d . . . . .
H17 H 1.140610 -0.058709 0.413782 0.064 Uiso 1 1 calc R U . . .
C18 C 0.9763(7) 0.0401(4) 0.3559(2) 0.0499(11) Uani 1 1 d . . . . .
H18 H 1.071933 0.027825 0.326237 0.060 Uiso 1 1 calc R U . . .
C19 C 0.5693(7) 0.5500(3) 0.37404(14) 0.0334(8) Uani 1 1 d . . . . .
C20 C 0.7288(7) 0.6126(4) 0.39989(15) 0.0386(9) Uani 1 1 d . . . . .
H20 H 0.870175 0.588636 0.395242 0.046 Uiso 1 1 calc R U . . .
C21 C 0.6790(7) 0.7112(4) 0.43274(15) 0.0399(9) Uani 1 1 d . . . . .
H21 H 0.787743 0.755324 0.450211 0.048 Uiso 1 1 calc R U . . .
C22 C 0.4773(7) 0.7452(4) 0.44023(14) 0.0397(10) Uani 1 1 d . . . . .
H22 H 0.446075 0.813741 0.462241 0.048 Uiso 1 1 calc R U . . .
C23 C 0.3165(7) 0.6804(4) 0.41585(17) 0.0437(10) Uani 1 1 d . . . . .
H23 H 0.175271 0.703263 0.421884 0.052 Uiso 1 1 calc R U . . .
C24 C 0.3624(7) 0.5818(4) 0.38257(16) 0.0384(9) Uani 1 1 d . . . . .
H24 H 0.253072 0.536677 0.365871 0.046 Uiso 1 1 calc R U . . .
C25 C 0.4577(8) 0.3252(4) 0.20542(17) 0.0539(12) Uani 1 1 d . . . . .
H25A H 0.416354 0.240558 0.206602 0.081 Uiso 1 1 calc R U . . .
H25B H 0.557844 0.337541 0.175106 0.081 Uiso 1 1 calc R U . . .
H25C H 0.333972 0.375184 0.199115 0.081 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
O2 C2 1.217(5) . ?
O6 C1 1.454(5) . ?
O6 C7 1.391(6) . ?
O7 C7 1.200(5) . ?
N3 N4 1.409(4) . ?
N3 C2 1.379(5) . ?
N3 C19 1.422(5) . ?
N4 C5 1.276(5) . ?
C1 C2 1.527(5) . ?
C1 C5 1.500(6) . ?
C1 C8 1.567(6) . ?
C5 C25 1.486(5) . ?
C7 C8 1.489(6) . ?
C8 H8 1.0000 . ?
C8 C9 1.517(6) . ?
C9 C10 1.437(6) . ?
C9 C18 1.364(6) . ?
C10 C11 1.419(6) . ?
C10 C15 1.422(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.365(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.406(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.367(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.405(6) . ?
C15 C16 1.412(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.364(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.414(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(5) . ?
C19 C24 1.386(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.358(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(6) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C7 O6 C1 91.7(3) . . ?
N4 N3 C19 117.1(3) . . ?
C2 N3 N4 112.9(3) . . ?
C2 N3 C19 129.3(3) . . ?
C5 N4 N3 108.3(3) . . ?
O6 C1 C2 113.8(3) . . ?
O6 C1 C5 114.5(3) . . ?
O6 C1 C8 89.4(3) . . ?
C2 C1 C8 118.4(3) . . ?
C5 C1 C2 101.8(3) . . ?
C5 C1 C8 119.6(4) . . ?
O2 C2 N3 128.8(4) . . ?
O2 C2 C1 127.2(4) . . ?
N3 C2 C1 103.9(3) . . ?
N4 C5 C1 112.4(3) . . ?
N4 C5 C25 122.2(4) . . ?
C25 C5 C1 125.4(4) . . ?
O6 C7 C8 95.1(3) . . ?
O7 C7 O6 125.0(5) . . ?
O7 C7 C8 139.9(5) . . ?
C1 C8 H8 110.5 . . ?
C7 C8 C1 83.8(3) . . ?
C7 C8 H8 110.5 . . ?
C7 C8 C9 117.6(4) . . ?
C9 C8 C1 121.3(3) . . ?
C9 C8 H8 110.5 . . ?
C10 C9 C8 120.1(4) . . ?
C18 C9 C8 120.5(4) . . ?
C18 C9 C10 119.4(4) . . ?
C11 C10 C9 122.7(4) . . ?
C11 C10 C15 117.9(4) . . ?
C15 C10 C9 119.4(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C10 119.6(4) . . ?
C14 C15 C16 121.9(4) . . ?
C16 C15 C10 118.5(4) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(4) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.7(4) . . ?
C18 C17 H17 120.2 . . ?
C9 C18 C17 121.4(5) . . ?
C9 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 N3 120.4(4) . . ?
C20 C19 C24 120.6(4) . . ?
C24 C19 N3 118.9(3) . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.0(4) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.2(4) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.9(4) . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 119.2(4) . . ?
C19 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C5 C25 H25A 109.5 . . ?
C5 C25 H25B 109.5 . . ?
C5 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O6 C1 C2 O2 -50.0(5) . . . . ?
O6 C1 C2 N3 130.9(3) . . . . ?
O6 C1 C5 N4 -128.8(4) . . . . ?
O6 C1 C5 C25 50.4(6) . . . . ?
O6 C1 C8 C7 0.8(3) . . . . ?
O6 C1 C8 C9 119.5(4) . . . . ?
O6 C7 C8 C1 -0.8(3) . . . . ?
O6 C7 C8 C9 -123.1(4) . . . . ?
O7 C7 C8 C1 177.1(7) . . . . ?
O7 C7 C8 C9 54.8(8) . . . . ?
N3 N4 C5 C1 1.4(5) . . . . ?
N3 N4 C5 C25 -177.8(4) . . . . ?
N3 C19 C20 C21 174.6(3) . . . . ?
N3 C19 C24 C23 -175.0(3) . . . . ?
N4 N3 C2 O2 173.8(4) . . . . ?
N4 N3 C2 C1 -7.2(4) . . . . ?
N4 N3 C19 C20 -143.9(4) . . . . ?
N4 N3 C19 C24 33.4(5) . . . . ?
C1 O6 C7 O7 -177.5(5) . . . . ?
C1 O6 C7 C8 0.9(3) . . . . ?
C1 C8 C9 C10 62.9(5) . . . . ?
C1 C8 C9 C18 -117.1(5) . . . . ?
C2 N3 N4 C5 3.9(4) . . . . ?
C2 N3 C19 C20 26.1(6) . . . . ?
C2 N3 C19 C24 -156.6(4) . . . . ?
C2 C1 C5 N4 -5.5(4) . . . . ?
C2 C1 C5 C25 173.7(4) . . . . ?
C2 C1 C8 C7 -116.1(4) . . . . ?
C2 C1 C8 C9 2.5(6) . . . . ?
C5 C1 C2 O2 -173.8(4) . . . . ?
C5 C1 C2 N3 7.2(4) . . . . ?
C5 C1 C8 C7 118.9(4) . . . . ?
C5 C1 C8 C9 -122.5(4) . . . . ?
C7 O6 C1 C2 120.1(4) . . . . ?
C7 O6 C1 C5 -123.3(4) . . . . ?
C7 O6 C1 C8 -0.9(3) . . . . ?
C7 C8 C9 C10 163.0(4) . . . . ?
C7 C8 C9 C18 -17.0(6) . . . . ?
C8 C1 C2 O2 53.0(6) . . . . ?
C8 C1 C2 N3 -126.1(4) . . . . ?
C8 C1 C5 N4 127.1(4) . . . . ?
C8 C1 C5 C25 -53.8(6) . . . . ?
C8 C9 C10 C11 1.6(6) . . . . ?
C8 C9 C10 C15 -178.7(4) . . . . ?
C8 C9 C18 C17 178.9(4) . . . . ?
C9 C10 C11 C12 -178.3(4) . . . . ?
C9 C10 C15 C14 178.9(4) . . . . ?
C9 C10 C15 C16 0.1(6) . . . . ?
C10 C9 C18 C17 -1.1(6) . . . . ?
C10 C11 C12 C13 -0.7(7) . . . . ?
C10 C15 C16 C17 -1.9(6) . . . . ?
C11 C10 C15 C14 -1.4(6) . . . . ?
C11 C10 C15 C16 179.9(4) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C15 1.8(7) . . . . ?
C13 C14 C15 C10 -0.5(6) . . . . ?
C13 C14 C15 C16 178.3(4) . . . . ?
C14 C15 C16 C17 179.4(4) . . . . ?
C15 C10 C11 C12 2.0(6) . . . . ?
C15 C16 C17 C18 2.2(7) . . . . ?
C16 C17 C18 C9 -0.6(7) . . . . ?
C18 C9 C10 C11 -178.4(4) . . . . ?
C18 C9 C10 C15 1.3(6) . . . . ?
C19 N3 N4 C5 175.6(3) . . . . ?
C19 N3 C2 O2 3.4(7) . . . . ?
C19 N3 C2 C1 -177.5(4) . . . . ?
C19 C20 C21 C22 0.9(6) . . . . ?
C20 C19 C24 C23 2.4(6) . . . . ?
C20 C21 C22 C23 1.2(6) . . . . ?
C21 C22 C23 C24 -1.5(6) . . . . ?
C22 C23 C24 C19 -0.3(6) . . . . ?
C24 C19 C20 C21 -2.7(6) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane'
_chemical_properties_physical    'X-ray sensitive'
####################################################################### 
# 
# 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_21
_audit_block_doi                 10.5517/ccdc.csd.cc2hp63j
_database_code_depnum_ccdc_archive 'CCDC 2314277'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2024-5l0dx 2024
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2023-12-13 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_audit_creation_date             2023-12-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 Cl N3 O4, C H Cl3'
_chemical_formula_sum            'C23 H23 Cl4 N3 O4'
_chemical_formula_weight         547.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.043(2)
_cell_length_b                   10.783(3)
_cell_length_c                   28.473(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2469.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4274
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.515
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1128
_exptl_crystal_preparation       Loop
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            32369
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.338
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Dectris PILATUS P200K'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
scan:
	Number of images: 324
	           Slice: -112.0000 - 50.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 160.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 346
	           Slice: -109.0000 - 64.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: -20.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 168
	           Slice: -88.0000 - -4.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 305.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 90
	           Slice: -102.0000 - -57.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 16.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 360
	           Slice: -112.0000 - 68.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 52.0000
	             XTD: 50.0488
	          2theta: -22.1712
scan:
	Number of images: 248
	           Slice: -79.5000 - 44.5000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 88.0000
	             XTD: 50.0488
	          2theta: -22.1712
;
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.053152
_diffrn_orient_matrix_UB_12      -0.040637
_diffrn_orient_matrix_UB_13      -0.104798
_diffrn_orient_matrix_UB_21      -0.037052
_diffrn_orient_matrix_UB_22      0.071232
_diffrn_orient_matrix_UB_23      -0.046414
_diffrn_orient_matrix_UB_31      0.028481
_diffrn_orient_matrix_UB_32      0.019340
_diffrn_orient_matrix_UB_33      0.006946
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             3.0
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3977
_reflns_number_total             4495
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0871P)²+1.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1390
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.98 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6), C31(H31)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.80181(16) 0.69989(14) 0.49550(4) 0.0504(4) Uani 1 1 d . . . . .
Cl31 Cl 0.8946(3) 0.07241(16) 0.50970(7) 0.0776(5) Uani 1 1 d . . . . .
Cl32 Cl 0.7192(3) 0.2200(2) 0.57836(7) 0.0852(6) Uani 1 1 d . . . . .
Cl33 Cl 0.8177(3) 0.3264(2) 0.48979(9) 0.1034(8) Uani 1 1 d . . . . .
O1 O 0.5692(4) 0.8903(3) 0.70694(11) 0.0328(7) Uani 1 1 d D . . . .
H1 H 0.577(8) 0.942(5) 0.7335(15) 0.056(17) Uiso 1 1 d D . . . .
O2 O 0.7908(4) 0.6633(3) 0.70544(11) 0.0402(8) Uani 1 1 d . . . . .
O7 O 0.4012(4) 0.5297(3) 0.71702(11) 0.0335(7) Uani 1 1 d . . . . .
O11 O 0.0381(4) 0.4379(3) 0.59203(12) 0.0417(8) Uani 1 1 d . . . . .
N3 N 0.6648(4) 0.6664(3) 0.77841(11) 0.0249(7) Uani 1 1 d . . . . .
N4 N 0.5139(4) 0.7093(3) 0.79809(12) 0.0261(7) Uani 1 1 d . . . . .
N8 N 0.1939(4) 0.5690(3) 0.66590(12) 0.0261(7) Uani 1 1 d . . . . .
C1 C 0.5217(5) 0.7676(3) 0.71908(14) 0.0235(8) Uani 1 1 d . . . . .
C2 C 0.6761(5) 0.6909(4) 0.73122(14) 0.0266(8) Uani 1 1 d . . . . .
C5 C 0.4319(5) 0.7640(3) 0.76619(14) 0.0246(8) Uani 1 1 d . . . . .
C6 C 0.4177(5) 0.7225(3) 0.67708(13) 0.0216(8) Uani 1 1 d . . . . .
H6 H 0.327312 0.784576 0.671779 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3348(5) 0.5983(3) 0.68820(14) 0.0236(8) Uani 1 1 d . . . . .
C9 C 0.1171(5) 0.6352(4) 0.62646(16) 0.0289(9) Uani 1 1 d . . . . .
H9A H 0.178811 0.712860 0.620227 0.035 Uiso 1 1 calc R U . . .
H9B H 0.000944 0.657094 0.634466 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1193(6) 0.5548(4) 0.58356(16) 0.0351(10) Uani 1 1 d . . . . .
H10A H 0.062482 0.598374 0.557493 0.042 Uiso 1 1 calc R U . . .
H10B H 0.235863 0.539669 0.573978 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1175(6) 0.3732(4) 0.62932(18) 0.0377(11) Uani 1 1 d . . . . .
H12A H 0.234498 0.356181 0.620700 0.045 Uiso 1 1 calc R U . . .
H12B H 0.060971 0.292796 0.634423 0.045 Uiso 1 1 calc R U . . .
C13 C 0.1126(6) 0.4482(4) 0.67407(17) 0.0347(10) Uani 1 1 d . . . . .
H13A H -0.004113 0.461185 0.683918 0.042 Uiso 1 1 calc R U . . .
H13B H 0.171073 0.402902 0.699418 0.042 Uiso 1 1 calc R U . . .
C14 C 0.5187(5) 0.7139(4) 0.63191(13) 0.0224(8) Uani 1 1 d . . . . .
C15 C 0.5497(5) 0.8217(4) 0.60650(14) 0.0269(9) Uani 1 1 d . . . . .
H15 H 0.509028 0.898804 0.617828 0.032 Uiso 1 1 calc R U . . .
C16 C 0.6392(5) 0.8181(4) 0.56480(15) 0.0297(9) Uani 1 1 d . . . . .
H16 H 0.660892 0.892058 0.547708 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6959(5) 0.7055(5) 0.54873(14) 0.0328(10) Uani 1 1 d . . . . .
C18 C 0.6681(6) 0.5971(4) 0.57328(16) 0.0330(10) Uani 1 1 d . . . . .
H18 H 0.708526 0.520119 0.561776 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5793(5) 0.6030(4) 0.61542(15) 0.0286(9) Uani 1 1 d . . . . .
H19 H 0.560575 0.529271 0.632909 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7767(5) 0.6011(4) 0.80839(15) 0.0276(9) Uani 1 1 d . . . . .
C21 C 0.9348(5) 0.5708(5) 0.79261(18) 0.0405(11) Uani 1 1 d . . . . .
H21 H 0.969919 0.593031 0.761888 0.049 Uiso 1 1 calc R U . . .
C22 C 1.0410(6) 0.5070(6) 0.8228(2) 0.0547(15) Uani 1 1 d . . . . .
H22 H 1.148773 0.484425 0.812164 0.066 Uiso 1 1 calc R U . . .
C23 C 0.9933(7) 0.4761(5) 0.8677(2) 0.0492(14) Uani 1 1 d . . . . .
H23 H 1.066848 0.432528 0.887929 0.059 Uiso 1 1 calc R U . . .
C24 C 0.8346(7) 0.5100(4) 0.88300(19) 0.0426(12) Uani 1 1 d . . . . .
H24 H 0.800020 0.489940 0.913983 0.051 Uiso 1 1 calc R U . . .
C25 C 0.7282(5) 0.5723(4) 0.85336(15) 0.0310(9) Uani 1 1 d . . . . .
H25 H 0.620695 0.595446 0.864056 0.037 Uiso 1 1 calc R U . . .
C26 C 0.2682(5) 0.8229(4) 0.77569(16) 0.0334(10) Uani 1 1 d . . . . .
H26A H 0.235800 0.807001 0.808312 0.050 Uiso 1 1 calc R U . . .
H26B H 0.184392 0.788072 0.754490 0.050 Uiso 1 1 calc R U . . .
H26C H 0.276626 0.912576 0.770528 0.050 Uiso 1 1 calc R U . . .
C31 C 0.8679(9) 0.2215(6) 0.5338(2) 0.0640(17) Uani 1 1 d . . . . .
H31 H 0.976174 0.247774 0.547929 0.077 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 C17 1.739(4) . ?
Cl31 C31 1.762(7) . ?
Cl32 C31 1.743(7) . ?
Cl33 C31 1.736(7) . ?
O1 H1 0.94(3) . ?
O1 C1 1.420(5) . ?
O2 C2 1.216(5) . ?
O7 C7 1.227(5) . ?
O11 C10 1.440(6) . ?
O11 C12 1.422(6) . ?
N3 N4 1.414(5) . ?
N3 C2 1.372(5) . ?
N3 C20 1.426(5) . ?
N4 C5 1.268(5) . ?
N8 C7 1.337(5) . ?
N8 C9 1.467(5) . ?
N8 C13 1.476(5) . ?
C1 C2 1.531(6) . ?
C1 C5 1.524(5) . ?
C1 C6 1.538(5) . ?
C5 C26 1.486(6) . ?
C6 H6 1.0000 . ?
C6 C7 1.529(5) . ?
C6 C14 1.524(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.498(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.509(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.392(6) . ?
C14 C19 1.374(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.376(7) . ?
C17 C18 1.380(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.398(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(6) . ?
C20 C25 1.374(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.393(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.376(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.397(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C31 H31 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
C1 O1 H1 112(4) . . ?
C12 O11 C10 110.5(3) . . ?
N4 N3 C20 117.7(3) . . ?
C2 N3 N4 112.4(3) . . ?
C2 N3 C20 129.7(3) . . ?
C5 N4 N3 108.3(3) . . ?
C7 N8 C9 127.3(3) . . ?
C7 N8 C13 120.6(4) . . ?
C9 N8 C13 111.3(3) . . ?
O1 C1 C2 109.9(3) . . ?
O1 C1 C5 111.5(3) . . ?
O1 C1 C6 104.6(3) . . ?
C2 C1 C6 116.4(3) . . ?
C5 C1 C2 99.9(3) . . ?
C5 C1 C6 114.7(3) . . ?
O2 C2 N3 126.5(4) . . ?
O2 C2 C1 127.7(4) . . ?
N3 C2 C1 105.7(3) . . ?
N4 C5 C1 113.3(3) . . ?
N4 C5 C26 121.9(4) . . ?
C26 C5 C1 124.7(4) . . ?
C1 C6 H6 107.5 . . ?
C7 C6 C1 110.7(3) . . ?
C7 C6 H6 107.5 . . ?
C14 C6 C1 112.7(3) . . ?
C14 C6 H6 107.5 . . ?
C14 C6 C7 110.7(3) . . ?
O7 C7 N8 122.9(4) . . ?
O7 C7 C6 118.5(4) . . ?
N8 C7 C6 118.6(3) . . ?
N8 C9 H9A 109.7 . . ?
N8 C9 H9B 109.7 . . ?
N8 C9 C10 109.8(3) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
O11 C10 C9 111.4(4) . . ?
O11 C10 H10A 109.4 . . ?
O11 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
O11 C12 C13 110.9(4) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
N8 C13 C12 109.1(4) . . ?
N8 C13 H13A 109.9 . . ?
N8 C13 H13B 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C15 C14 C6 118.9(3) . . ?
C19 C14 C6 122.0(4) . . ?
C19 C14 C15 119.1(4) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(4) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 Cl1 118.9(4) . . ?
C16 C17 C18 121.7(4) . . ?
C18 C17 Cl1 119.4(4) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.6(4) . . ?
C19 C18 H18 120.7 . . ?
C14 C19 C18 120.9(4) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 N3 120.0(4) . . ?
C25 C20 N3 119.4(4) . . ?
C25 C20 C21 120.6(4) . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.6(5) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.5(5) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.6 . . ?
C22 C23 C24 118.8(5) . . ?
C24 C23 H23 120.6 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.3(4) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C5 C26 H26A 109.5 . . ?
C5 C26 H26B 109.5 . . ?
C5 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
Cl31 C31 H31 108.0 . . ?
Cl32 C31 Cl31 111.0(4) . . ?
Cl32 C31 H31 108.0 . . ?
Cl33 C31 Cl31 109.9(3) . . ?
Cl33 C31 Cl32 111.9(4) . . ?
Cl33 C31 H31 108.0 . . ?

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
_geom_hbond_publ_flag
O1 H1 O7 0.94(3) 1.70(3) 2.646(4) 176(6) 3_656 yes

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
Cl1 C17 C18 C19 -178.5(3) . . . . ?
O1 C1 C2 O2 -63.6(5) . . . . ?
O1 C1 C2 N3 112.3(3) . . . . ?
O1 C1 C5 N4 -112.2(4) . . . . ?
O1 C1 C5 C26 65.0(5) . . . . ?
O1 C1 C6 C7 -171.3(3) . . . . ?
O1 C1 C6 C14 64.1(4) . . . . ?
O11 C12 C13 N8 -57.9(5) . . . . ?
N3 N4 C5 C1 -1.2(4) . . . . ?
N3 N4 C5 C26 -178.4(4) . . . . ?
N3 C20 C21 C22 179.9(4) . . . . ?
N3 C20 C25 C24 -179.6(4) . . . . ?
N4 N3 C2 O2 -179.2(4) . . . . ?
N4 N3 C2 C1 4.9(4) . . . . ?
N4 N3 C20 C21 -171.8(4) . . . . ?
N4 N3 C20 C25 6.0(5) . . . . ?
N8 C9 C10 O11 56.3(5) . . . . ?
C1 C6 C7 O7 -26.8(5) . . . . ?
C1 C6 C7 N8 153.6(3) . . . . ?
C1 C6 C14 C15 -79.7(4) . . . . ?
C1 C6 C14 C19 100.6(4) . . . . ?
C2 N3 N4 C5 -2.5(5) . . . . ?
C2 N3 C20 C21 11.6(6) . . . . ?
C2 N3 C20 C25 -170.6(4) . . . . ?
C2 C1 C5 N4 3.9(4) . . . . ?
C2 C1 C5 C26 -178.9(4) . . . . ?
C2 C1 C6 C7 67.3(4) . . . . ?
C2 C1 C6 C14 -57.4(4) . . . . ?
C5 C1 C2 O2 179.2(4) . . . . ?
C5 C1 C2 N3 -5.0(4) . . . . ?
C5 C1 C6 C7 -48.8(4) . . . . ?
C5 C1 C6 C14 -173.5(3) . . . . ?
C6 C1 C2 O2 55.1(6) . . . . ?
C6 C1 C2 N3 -129.1(3) . . . . ?
C6 C1 C5 N4 129.2(4) . . . . ?
C6 C1 C5 C26 -53.6(5) . . . . ?
C6 C14 C15 C16 -179.1(4) . . . . ?
C6 C14 C19 C18 178.4(4) . . . . ?
C7 N8 C9 C10 114.4(5) . . . . ?
C7 N8 C13 C12 -114.6(4) . . . . ?
C7 C6 C14 C15 155.7(4) . . . . ?
C7 C6 C14 C19 -24.0(5) . . . . ?
C9 N8 C7 O7 -170.7(4) . . . . ?
C9 N8 C7 C6 8.8(6) . . . . ?
C9 N8 C13 C12 55.8(5) . . . . ?
C10 O11 C12 C13 59.8(5) . . . . ?
C12 O11 C10 C9 -59.1(5) . . . . ?
C13 N8 C7 O7 -1.9(6) . . . . ?
C13 N8 C7 C6 177.6(3) . . . . ?
C13 N8 C9 C10 -55.3(5) . . . . ?
C14 C6 C7 O7 98.9(4) . . . . ?
C14 C6 C7 N8 -80.7(4) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C14 C19 C18 -1.3(6) . . . . ?
C15 C16 C17 Cl1 177.8(3) . . . . ?
C15 C16 C17 C18 -1.0(7) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C17 C18 C19 C14 0.9(7) . . . . ?
C19 C14 C15 C16 0.6(6) . . . . ?
C20 N3 N4 C5 -179.7(3) . . . . ?
C20 N3 C2 O2 -2.4(7) . . . . ?
C20 N3 C2 C1 -178.3(4) . . . . ?
C20 C21 C22 C23 -1.2(8) . . . . ?
C21 C20 C25 C24 -1.7(6) . . . . ?
C21 C22 C23 C24 -0.1(8) . . . . ?
C22 C23 C24 C25 0.5(8) . . . . ?
C23 C24 C25 C20 0.4(7) . . . . ?
C25 C20 C21 C22 2.1(7) . . . . ?


#==END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane/ethyl acetate'
