# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_1-ab-40bx3
_audit_block_doi                 10.5517/ccdc.csd.cc2g0wgv
_database_code_depnum_ccdc_archive 'CCDC 2264967'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c03131 2023
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT971_1-ab-40bx3          
;
PROBLEM: Check Calcd Resid. Dens.  0.92Ang From I2              2.64 eA-3  
RESPONSE: The large positive and negative electron densities in the difference 
electron density map are all near the I atom.  These fluctuations are likely 
due to series termination effects.
;
# end Validation Reply Form
_audit_creation_date             2023-05-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 I N2 O6'
_chemical_formula_sum            'C17 H15 I N2 O6'
_chemical_formula_weight         470.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H15N2O4I
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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.8128(4)
_cell_length_b                   11.8787(6)
_cell_length_c                   13.9111(5)
_cell_angle_alpha                96.120(4)
_cell_angle_beta                 91.980(3)
_cell_angle_gamma                96.465(4)
_cell_volume                     1763.32(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10217
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      76.3520
_cell_measurement_theta_min      3.2090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.611
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.890
_diffrn_reflns_theta_min         3.199
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -35.00   0.50    4.50    --  -48.08 -53.00  28.00  168
  2  ω     36.00 120.00   0.50    4.50    --   48.08  53.00 172.00  168
  3  ω    -23.00  57.00   0.50    4.50    --   48.08 -53.00  28.00  160
  4  ω   -176.00 -92.00   0.50   20.00    -- -105.11 -53.00  28.00  168
  5  ω    -63.00 -33.00   0.50   20.00    -- -105.11  53.00 172.00   60
  6  ω     93.00 176.00   0.50   20.00    --  105.11  53.00 172.00  166
  7  ω    -26.00  26.00   0.50    4.50    --  -48.08  19.00 120.00  104
  8  ω    -61.00  24.00   0.50    4.50    --  -48.08  53.00 172.00  170
  9  ω    -92.00 -13.00   0.50    4.50    --  -48.08 125.00 -60.00  158
 10  ω    -25.00  20.00   0.50    4.50    --   48.08 -19.00-120.00   90
 11  ω    -24.00  39.00   0.50    4.50    --   48.08 -38.00-150.00  126
 12  ω    -25.00  20.00   0.50    4.50    --   48.08 -19.00  90.00   90
 13  ω   -174.00 -87.00   0.50   20.00    -- -105.11-125.00 150.00  174
 14  ω   -176.00 -90.00   0.50   20.00    -- -105.11 -61.00 -30.00  172
 15  ω   -111.00 -36.00   0.50   20.00    -- -105.11 125.00   0.00  150
 16  ω   -174.00 -87.00   0.50   20.00    -- -105.11-125.00  90.00  174
 17  ω   -125.00 -33.00   0.50   20.00    -- -105.11 143.00  84.79  184
 18  ω   -176.00 -90.00   0.50   20.00    -- -105.11 -61.00 -41.44  172
 19  ω   -176.00-100.00   0.50   20.00    -- -105.11 -95.00 120.00  152
 20  ω    -75.00 -33.00   0.50   20.00    -- -105.11  61.00  90.00   84
 21  ω   -109.00 -37.00   0.50   20.00    -- -105.11 115.00  52.19  144
 22  ω   -116.00 -33.00   0.50   20.00    -- -105.11  77.00 120.00  166
 23  ω   -177.00 -95.00   0.50   20.00    -- -105.11 -15.00   0.00  164
 24  ω   -111.00 -36.00   0.50   20.00    -- -105.11 125.00-120.00  150
 25  ω   -111.00 -36.00   0.50   20.00    -- -105.11 125.00 150.00  150
 26  ω    -75.00 -33.00   0.50   20.00    -- -105.11  61.00  30.00   84
 27  ω    -90.00 -35.00   0.50   20.00    -- -105.11 104.00-121.59  110
 28  ω     33.00 105.00   0.50   20.00    --  105.11 -95.00   0.00  144
 29  ω     94.00 176.00   0.50   20.00    --  105.11  45.00  30.00  164
 30  ω     33.00 105.00   0.50   20.00    --  105.11 -95.00 -60.00  144
 31  ω     36.00 112.00   0.50   20.00    --  105.11-125.00-180.00  152
 32  ω     36.00 120.00   0.50    4.50    --   48.08  52.00 125.81  168
 33  ω     35.00 120.00   0.50    4.50    --   48.08  56.00  -6.17  170
 34  ω     36.00 120.00   0.50    4.50    --   48.08  53.00 -56.93  168
 35  ω     35.00 120.00   0.50    4.50    --   48.08  54.00-150.17  170
 36  ω     35.00 120.00   0.50    4.50    --   48.08  56.00-114.34  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0463695000
_diffrn_orient_matrix_UB_12      0.1184245000
_diffrn_orient_matrix_UB_13      0.0126135000
_diffrn_orient_matrix_UB_21      -0.1122626000
_diffrn_orient_matrix_UB_22      -0.0446662000
_diffrn_orient_matrix_UB_23      -0.0702860000
_diffrn_orient_matrix_UB_31      -0.0765030000
_diffrn_orient_matrix_UB_32      -0.0350725000
_diffrn_orient_matrix_UB_33      0.0856359000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6969
_reflns_number_total             7208
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.519
_refine_diff_density_min         -1.428
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7208
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0895P)²+5.9843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1437
_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. Restrained distances
 N3-H3 = N1-H1
 0.84 with sigma of 0.02
 O5-H5 = O11-H11
 0.84 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C29(H29), C30(H30), C31(H31), C32(H32)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C17(H17A,H17B,H17C), C23(H23A,H23B,H23C),
 C25(H25A,H25B,H25C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.14134(3) 0.74723(3) 0.70244(2) 0.03159(12) Uani 1 1 d . . . . .
I2 I 0.35156(3) 0.72202(3) 0.20240(2) 0.03096(12) Uani 1 1 d . . . . .
O1 O -0.1058(4) 0.8589(4) 0.7862(3) 0.0456(10) Uani 1 1 d . . . . .
O2 O -0.2500(4) 0.9184(3) 0.6875(3) 0.0406(9) Uani 1 1 d . . . . .
O3 O -0.0151(4) 0.8937(3) 0.2948(3) 0.0381(8) Uani 1 1 d . . . . .
O4 O -0.2047(4) 0.8897(4) 0.3543(3) 0.0422(9) Uani 1 1 d . . . . .
O5 O 0.1591(4) 0.7738(3) 0.3450(3) 0.0384(8) Uani 1 1 d D . . . .
H5 H 0.125(6) 0.828(4) 0.325(5) 0.05(2) Uiso 1 1 d D . . . .
O6 O 0.3046(3) 0.9544(3) 0.4888(4) 0.0417(9) Uani 1 1 d . . . . .
O7 O 0.6085(4) 0.6170(4) 0.2760(3) 0.0470(10) Uani 1 1 d . . . . .
O8 O 0.7771(3) 0.6274(3) 0.1851(3) 0.0366(8) Uani 1 1 d . . . . .
O9 O 0.5385(4) 0.6599(4) -0.2181(3) 0.0416(9) Uani 1 1 d . . . . .
O10 O 0.7037(4) 0.5934(4) -0.1560(3) 0.0425(9) Uani 1 1 d . . . . .
O11 O 0.3105(3) 0.6421(3) -0.1563(3) 0.0355(8) Uani 1 1 d D . . . .
H11 H 0.379(4) 0.652(7) -0.183(5) 0.05(2) Uiso 1 1 d D . . . .
O12 O 0.1834(3) 0.5391(3) -0.0018(3) 0.0343(8) Uani 1 1 d . . . . .
N1 N -0.1251(3) 0.8819(3) 0.5315(3) 0.0248(8) Uani 1 1 d D . . . .
H1 H -0.191(5) 0.910(7) 0.522(6) 0.07(3) Uiso 1 1 d D . . . .
N2 N 0.3725(4) 0.7832(4) 0.5153(4) 0.0399(11) Uani 1 1 d . . . . .
N3 N 0.6366(3) 0.6219(3) 0.0230(3) 0.0248(8) Uani 1 1 d D . . . .
H3 H 0.709(3) 0.605(5) 0.017(4) 0.023(13) Uiso 1 1 d D . . . .
N4 N 0.1299(4) 0.7214(4) 0.0037(4) 0.0398(11) Uani 1 1 d . . . . .
C1 C -0.0779(4) 0.8555(4) 0.6169(4) 0.0242(9) Uani 1 1 d . . . . .
C2 C 0.0333(4) 0.8099(4) 0.5977(3) 0.0237(8) Uani 1 1 d . . . . .
C3 C 0.0545(4) 0.8117(4) 0.4983(3) 0.0216(8) Uani 1 1 d . . . . .
C4 C -0.0470(4) 0.8583(4) 0.4592(3) 0.0237(9) Uani 1 1 d . . . . .
C5 C -0.1420(5) 0.8767(4) 0.7074(4) 0.0331(11) Uani 1 1 d . . . . .
C6 C -0.3209(7) 0.9465(6) 0.7708(6) 0.0529(16) Uani 1 1 d . . . . .
H6A H -0.274066 1.009190 0.813246 0.079 Uiso 1 1 calc R U . . .
H6B H -0.336310 0.879631 0.806201 0.079 Uiso 1 1 calc R U . . .
H6C H -0.400673 0.969776 0.749584 0.079 Uiso 1 1 calc R U . . .
C7 C -0.0836(5) 0.8818(4) 0.3610(4) 0.0317(10) Uani 1 1 d . . . . .
C8 C -0.2534(7) 0.9189(6) 0.2625(6) 0.0574(19) Uani 1 1 d . . . . .
H8A H -0.343282 0.922503 0.265541 0.086 Uiso 1 1 calc R U . . .
H8B H -0.237702 0.860646 0.210389 0.086 Uiso 1 1 calc R U . . .
H8C H -0.211981 0.993146 0.249705 0.086 Uiso 1 1 calc R U . . .
C9 C 0.1672(4) 0.7733(4) 0.4465(4) 0.0272(9) Uani 1 1 d . . . . .
C10 C 0.2877(4) 0.8518(4) 0.4870(4) 0.0321(11) Uani 1 1 d . . . . .
C11 C 0.3217(4) 0.6688(4) 0.5058(4) 0.0326(11) Uani 1 1 d . . . . .
C12 C 0.3740(5) 0.5766(5) 0.5346(4) 0.0369(11) Uani 1 1 d . . . . .
H12 H 0.455677 0.585523 0.563945 0.044 Uiso 1 1 calc R U . . .
C13 C 0.3043(5) 0.4706(4) 0.5196(4) 0.0348(11) Uani 1 1 d . . . . .
H13 H 0.339224 0.405771 0.538126 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1840(5) 0.4572(4) 0.4778(4) 0.0326(10) Uani 1 1 d . . . . .
H14 H 0.137834 0.383714 0.467843 0.039 Uiso 1 1 calc R U . . .
C15 C 0.1307(4) 0.5523(4) 0.4504(4) 0.0282(9) Uani 1 1 d . . . . .
H15 H 0.048577 0.543753 0.421860 0.034 Uiso 1 1 calc R U . . .
C16 C 0.1994(4) 0.6580(4) 0.4655(4) 0.0267(9) Uani 1 1 d . . . . .
C17 C 0.4979(5) 0.8242(5) 0.5544(7) 0.063(2) Uani 1 1 d . . . . .
H17A H 0.508461 0.907758 0.563117 0.094 Uiso 1 1 calc R U . . .
H17B H 0.558716 0.797015 0.509545 0.094 Uiso 1 1 calc R U . . .
H17C H 0.510947 0.795530 0.617061 0.094 Uiso 1 1 calc R U . . .
C18 C 0.5865(4) 0.6413(4) 0.1103(4) 0.0255(9) Uani 1 1 d . . . . .
C19 C 0.4673(4) 0.6731(4) 0.0936(3) 0.0225(8) Uani 1 1 d . . . . .
C20 C 0.4454(4) 0.6704(4) -0.0068(3) 0.0228(8) Uani 1 1 d . . . . .
C21 C 0.5545(4) 0.6384(4) -0.0491(3) 0.0237(8) Uani 1 1 d . . . . .
C22 C 0.6545(5) 0.6266(4) 0.1998(4) 0.0312(10) Uani 1 1 d . . . . .
C23 C 0.8526(6) 0.5972(5) 0.2645(5) 0.0447(14) Uani 1 1 d . . . . .
H23A H 0.836565 0.643459 0.324391 0.067 Uiso 1 1 calc R U . . .
H23B H 0.940960 0.611363 0.250802 0.067 Uiso 1 1 calc R U . . .
H23C H 0.831315 0.516274 0.271927 0.067 Uiso 1 1 calc R U . . .
C24 C 0.5943(5) 0.6311(4) -0.1494(4) 0.0341(11) Uani 1 1 d . . . . .
C25 C 0.7513(7) 0.5785(6) -0.2527(5) 0.0556(17) Uani 1 1 d . . . . .
H25A H 0.828134 0.542149 -0.250240 0.083 Uiso 1 1 calc R U . . .
H25B H 0.768810 0.653136 -0.276578 0.083 Uiso 1 1 calc R U . . .
H25C H 0.688995 0.530390 -0.296335 0.083 Uiso 1 1 calc R U . . .
C26 C 0.3260(4) 0.6944(4) -0.0589(4) 0.0286(10) Uani 1 1 d . . . . .
C27 C 0.2070(4) 0.6387(4) -0.0131(4) 0.0310(10) Uani 1 1 d . . . . .
C28 C 0.1883(5) 0.8285(4) -0.0127(5) 0.0368(12) Uani 1 1 d . . . . .
C29 C 0.1437(5) 0.9326(5) 0.0060(6) 0.0519(17) Uani 1 1 d . . . . .
H29 H 0.064795 0.938809 0.032855 0.062 Uiso 1 1 calc R U . . .
C30 C 0.2196(6) 1.0284(5) -0.0162(6) 0.0501(16) Uani 1 1 d . . . . .
H30 H 0.190535 1.101073 -0.005830 0.060 Uiso 1 1 calc R U . . .
C31 C 0.3355(6) 1.0206(5) -0.0529(5) 0.0412(13) Uani 1 1 d . . . . .
H31 H 0.385181 1.087339 -0.067254 0.049 Uiso 1 1 calc R U . . .
C32 C 0.3805(5) 0.9130(5) -0.0691(4) 0.0347(11) Uani 1 1 d . . . . .
H32 H 0.460469 0.906478 -0.093888 0.042 Uiso 1 1 calc R U . . .
C33 C 0.3063(4) 0.8193(4) -0.0483(4) 0.0295(10) Uani 1 1 d . . . . .
C34 C 0.0089(5) 0.7023(5) 0.0459(7) 0.060(2) Uani 1 1 d . . . . .
H34A H 0.009240 0.750769 0.107573 0.090 Uiso 1 1 calc R U . . .
H34B H -0.008059 0.622101 0.057140 0.090 Uiso 1 1 calc R U . . .
H34C H -0.055957 0.721296 0.001454 0.090 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
I1 C2 2.086(4) . ?
I2 C19 2.074(4) . ?
O1 C5 1.199(7) . ?
O2 C5 1.350(7) . ?
O2 C6 1.442(7) . ?
O3 C7 1.211(7) . ?
O4 C7 1.323(7) . ?
O4 C8 1.456(7) . ?
O5 H5 0.84(2) . ?
O5 C9 1.411(6) . ?
O6 C10 1.209(6) . ?
O7 C22 1.197(7) . ?
O8 C22 1.348(6) . ?
O8 C23 1.450(6) . ?
O9 C24 1.214(7) . ?
O10 C24 1.314(7) . ?
O10 C25 1.457(7) . ?
O11 H11 0.85(2) . ?
O11 C26 1.426(6) . ?
O12 C27 1.210(6) . ?
N1 H1 0.84(2) . ?
N1 C1 1.358(6) . ?
N1 C4 1.363(6) . ?
N2 C10 1.368(7) . ?
N2 C11 1.398(7) . ?
N2 C17 1.455(7) . ?
N3 H3 0.83(2) . ?
N3 C18 1.355(6) . ?
N3 C21 1.360(6) . ?
N4 C27 1.366(6) . ?
N4 C28 1.400(7) . ?
N4 C34 1.457(8) . ?
C1 C2 1.395(6) . ?
C1 C5 1.470(7) . ?
C2 C3 1.411(6) . ?
C3 C4 1.402(6) . ?
C3 C9 1.527(6) . ?
C4 C7 1.473(7) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.565(7) . ?
C9 C16 1.498(7) . ?
C11 C12 1.377(7) . ?
C11 C16 1.405(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.391(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.406(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.402(6) . ?
C18 C22 1.460(7) . ?
C19 C20 1.406(7) . ?
C20 C21 1.409(6) . ?
C20 C26 1.528(6) . ?
C21 C24 1.471(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.565(7) . ?
C26 C33 1.515(7) . ?
C28 C29 1.380(8) . ?
C28 C33 1.396(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.395(9) . ?
C30 H30 0.9500 . ?
C30 C31 1.378(9) . ?
C31 H31 0.9500 . ?
C31 C32 1.417(8) . ?
C32 H32 0.9500 . ?
C32 C33 1.360(7) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C5 O2 C6 114.8(5) . . ?
C7 O4 C8 116.3(5) . . ?
C9 O5 H5 115(5) . . ?
C22 O8 C23 115.8(5) . . ?
C24 O10 C25 116.4(5) . . ?
C26 O11 H11 109(5) . . ?
C1 N1 H1 128(6) . . ?
C1 N1 C4 110.4(4) . . ?
C4 N1 H1 122(6) . . ?
C10 N2 C11 111.5(4) . . ?
C10 N2 C17 124.4(5) . . ?
C11 N2 C17 124.1(5) . . ?
C18 N3 H3 123(4) . . ?
C18 N3 C21 110.3(4) . . ?
C21 N3 H3 127(4) . . ?
C27 N4 C28 111.5(4) . . ?
C27 N4 C34 123.6(5) . . ?
C28 N4 C34 124.4(5) . . ?
N1 C1 C2 107.0(4) . . ?
N1 C1 C5 121.4(4) . . ?
C2 C1 C5 131.6(5) . . ?
C1 C2 I1 123.4(3) . . ?
C1 C2 C3 108.5(4) . . ?
C3 C2 I1 128.1(3) . . ?
C2 C3 C9 126.2(4) . . ?
C4 C3 C2 105.7(4) . . ?
C4 C3 C9 128.0(4) . . ?
N1 C4 C3 108.3(4) . . ?
N1 C4 C7 117.9(4) . . ?
C3 C4 C7 133.8(4) . . ?
O1 C5 O2 125.1(5) . . ?
O1 C5 C1 126.0(5) . . ?
O2 C5 C1 108.9(5) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O4 123.6(5) . . ?
O3 C7 C4 126.3(5) . . ?
O4 C7 C4 110.1(5) . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 C3 114.4(4) . . ?
O5 C9 C10 108.2(4) . . ?
O5 C9 C16 106.9(4) . . ?
C3 C9 C10 109.6(4) . . ?
C16 C9 C3 115.1(4) . . ?
C16 C9 C10 101.6(4) . . ?
O6 C10 N2 126.3(5) . . ?
O6 C10 C9 125.9(5) . . ?
N2 C10 C9 107.7(4) . . ?
N2 C11 C16 109.7(4) . . ?
C12 C11 N2 128.4(5) . . ?
C12 C11 C16 121.8(5) . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.2(5) . . ?
C13 C12 H12 120.9 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.6 . . ?
C11 C16 C9 109.2(4) . . ?
C15 C16 C9 131.0(4) . . ?
C15 C16 C11 119.8(4) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 107.4(4) . . ?
N3 C18 C22 121.3(4) . . ?
C19 C18 C22 131.3(4) . . ?
C18 C19 I2 124.1(3) . . ?
C18 C19 C20 108.2(4) . . ?
C20 C19 I2 127.7(3) . . ?
C19 C20 C21 105.8(4) . . ?
C19 C20 C26 126.7(4) . . ?
C21 C20 C26 127.4(4) . . ?
N3 C21 C20 108.3(4) . . ?
N3 C21 C24 119.1(4) . . ?
C20 C21 C24 132.3(4) . . ?
O7 C22 O8 124.5(5) . . ?
O7 C22 C18 125.0(5) . . ?
O8 C22 C18 110.4(4) . . ?
O8 C23 H23A 109.5 . . ?
O8 C23 H23B 109.5 . . ?
O8 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O9 C24 O10 122.6(5) . . ?
O9 C24 C21 126.0(5) . . ?
O10 C24 C21 111.3(5) . . ?
O10 C25 H25A 109.5 . . ?
O10 C25 H25B 109.5 . . ?
O10 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O11 C26 C20 113.4(4) . . ?
O11 C26 C27 101.6(4) . . ?
O11 C26 C33 113.4(4) . . ?
C20 C26 C27 111.7(4) . . ?
C33 C26 C20 113.5(4) . . ?
C33 C26 C27 102.0(4) . . ?
O12 C27 N4 126.2(5) . . ?
O12 C27 C26 126.5(4) . . ?
N4 C27 C26 107.1(4) . . ?
C29 C28 N4 127.5(5) . . ?
C29 C28 C33 121.8(5) . . ?
C33 C28 N4 110.6(4) . . ?
C28 C29 H29 121.5 . . ?
C28 C29 C30 117.0(6) . . ?
C30 C29 H29 121.5 . . ?
C29 C30 H30 119.1 . . ?
C31 C30 C29 121.9(5) . . ?
C31 C30 H30 119.1 . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.0(5) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.9 . . ?
C33 C32 C31 118.3(5) . . ?
C33 C32 H32 120.9 . . ?
C28 C33 C26 108.0(4) . . ?
C32 C33 C26 131.0(5) . . ?
C32 C33 C28 121.0(5) . . ?
N4 C34 H34A 109.5 . . ?
N4 C34 H34B 109.5 . . ?
N4 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
I1 C2 C3 C4 177.8(3) . . . . ?
I1 C2 C3 C9 -3.7(7) . . . . ?
I2 C19 C20 C21 176.3(3) . . . . ?
I2 C19 C20 C26 -5.2(7) . . . . ?
O5 C9 C10 O6 68.9(7) . . . . ?
O5 C9 C10 N2 -108.1(5) . . . . ?
O5 C9 C16 C11 110.6(5) . . . . ?
O5 C9 C16 C15 -69.7(6) . . . . ?
O11 C26 C27 O12 65.7(6) . . . . ?
O11 C26 C27 N4 -109.0(5) . . . . ?
O11 C26 C33 C28 102.6(5) . . . . ?
O11 C26 C33 C32 -75.9(7) . . . . ?
N1 C1 C2 I1 -177.0(3) . . . . ?
N1 C1 C2 C3 1.4(5) . . . . ?
N1 C1 C5 O1 -177.9(5) . . . . ?
N1 C1 C5 O2 2.9(6) . . . . ?
N1 C4 C7 O3 160.1(5) . . . . ?
N1 C4 C7 O4 -19.3(6) . . . . ?
N2 C11 C12 C13 178.5(6) . . . . ?
N2 C11 C16 C9 0.3(6) . . . . ?
N2 C11 C16 C15 -179.4(5) . . . . ?
N3 C18 C19 I2 -176.3(3) . . . . ?
N3 C18 C19 C20 1.1(5) . . . . ?
N3 C18 C22 O7 -162.4(5) . . . . ?
N3 C18 C22 O8 18.7(6) . . . . ?
N3 C21 C24 O9 -168.5(5) . . . . ?
N3 C21 C24 O10 8.5(6) . . . . ?
N4 C28 C29 C30 179.7(6) . . . . ?
N4 C28 C33 C26 1.7(6) . . . . ?
N4 C28 C33 C32 -179.7(5) . . . . ?
C1 N1 C4 C3 1.5(5) . . . . ?
C1 N1 C4 C7 180.0(4) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C9 178.0(4) . . . . ?
C2 C1 C5 O1 1.5(9) . . . . ?
C2 C1 C5 O2 -177.7(5) . . . . ?
C2 C3 C4 N1 -0.5(5) . . . . ?
C2 C3 C4 C7 -178.8(5) . . . . ?
C2 C3 C9 O5 174.2(4) . . . . ?
C2 C3 C9 C10 -64.1(6) . . . . ?
C2 C3 C9 C16 49.7(6) . . . . ?
C3 C4 C7 O3 -21.8(8) . . . . ?
C3 C4 C7 O4 158.8(5) . . . . ?
C3 C9 C10 O6 -56.5(7) . . . . ?
C3 C9 C10 N2 126.5(5) . . . . ?
C3 C9 C16 C11 -121.1(5) . . . . ?
C3 C9 C16 C15 58.6(7) . . . . ?
C4 N1 C1 C2 -1.8(5) . . . . ?
C4 N1 C1 C5 177.8(4) . . . . ?
C4 C3 C9 O5 -7.6(7) . . . . ?
C4 C3 C9 C10 114.1(5) . . . . ?
C4 C3 C9 C16 -132.1(5) . . . . ?
C5 C1 C2 I1 3.5(7) . . . . ?
C5 C1 C2 C3 -178.1(5) . . . . ?
C6 O2 C5 O1 2.6(8) . . . . ?
C6 O2 C5 C1 -178.2(4) . . . . ?
C8 O4 C7 O3 -2.6(7) . . . . ?
C8 O4 C7 C4 176.8(5) . . . . ?
C9 C3 C4 N1 -179.1(4) . . . . ?
C9 C3 C4 C7 2.7(8) . . . . ?
C10 N2 C11 C12 -173.8(6) . . . . ?
C10 N2 C11 C16 2.7(7) . . . . ?
C10 C9 C16 C11 -2.7(5) . . . . ?
C10 C9 C16 C15 177.0(5) . . . . ?
C11 N2 C10 O6 178.6(6) . . . . ?
C11 N2 C10 C9 -4.4(7) . . . . ?
C11 C12 C13 C14 -0.9(9) . . . . ?
C12 C11 C16 C9 177.1(5) . . . . ?
C12 C11 C16 C15 -2.7(8) . . . . ?
C12 C13 C14 C15 -0.3(8) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C9 -178.3(5) . . . . ?
C14 C15 C16 C11 1.4(7) . . . . ?
C16 C9 C10 O6 -178.7(6) . . . . ?
C16 C9 C10 N2 4.2(6) . . . . ?
C16 C11 C12 C13 2.4(9) . . . . ?
C17 N2 C10 O6 1.2(11) . . . . ?
C17 N2 C10 C9 178.2(6) . . . . ?
C17 N2 C11 C12 3.6(11) . . . . ?
C17 N2 C11 C16 -179.9(7) . . . . ?
C18 N3 C21 C20 0.1(5) . . . . ?
C18 N3 C21 C24 175.0(4) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C18 C19 C20 C26 177.5(4) . . . . ?
C19 C18 C22 O7 16.5(9) . . . . ?
C19 C18 C22 O8 -162.4(5) . . . . ?
C19 C20 C21 N3 0.6(5) . . . . ?
C19 C20 C21 C24 -173.4(5) . . . . ?
C19 C20 C26 O11 -155.8(4) . . . . ?
C19 C20 C26 C27 -41.7(6) . . . . ?
C19 C20 C26 C33 73.0(6) . . . . ?
C20 C21 C24 O9 4.9(9) . . . . ?
C20 C21 C24 O10 -178.1(5) . . . . ?
C20 C26 C27 O12 -55.4(7) . . . . ?
C20 C26 C27 N4 129.8(5) . . . . ?
C20 C26 C33 C28 -126.2(5) . . . . ?
C20 C26 C33 C32 55.4(7) . . . . ?
C21 N3 C18 C19 -0.7(5) . . . . ?
C21 N3 C18 C22 178.4(4) . . . . ?
C21 C20 C26 O11 22.4(7) . . . . ?
C21 C20 C26 C27 136.5(5) . . . . ?
C21 C20 C26 C33 -108.8(5) . . . . ?
C22 C18 C19 I2 4.6(7) . . . . ?
C22 C18 C19 C20 -178.0(5) . . . . ?
C23 O8 C22 O7 9.7(7) . . . . ?
C23 O8 C22 C18 -171.4(4) . . . . ?
C25 O10 C24 O9 -4.9(8) . . . . ?
C25 O10 C24 C21 177.9(5) . . . . ?
C26 C20 C21 N3 -177.9(4) . . . . ?
C26 C20 C21 C24 8.1(8) . . . . ?
C27 N4 C28 C29 -173.1(7) . . . . ?
C27 N4 C28 C33 4.1(7) . . . . ?
C27 C26 C33 C28 -5.9(5) . . . . ?
C27 C26 C33 C32 175.7(5) . . . . ?
C28 N4 C27 O12 177.4(6) . . . . ?
C28 N4 C27 C26 -7.8(6) . . . . ?
C28 C29 C30 C31 -1.7(11) . . . . ?
C29 C28 C33 C26 179.1(6) . . . . ?
C29 C28 C33 C32 -2.3(9) . . . . ?
C29 C30 C31 C32 0.1(10) . . . . ?
C30 C31 C32 C33 0.5(8) . . . . ?
C31 C32 C33 C26 178.9(5) . . . . ?
C31 C32 C33 C28 0.6(8) . . . . ?
C33 C26 C27 O12 -177.0(5) . . . . ?
C33 C26 C27 N4 8.2(5) . . . . ?
C33 C28 C29 C30 2.7(10) . . . . ?
C34 N4 C27 O12 5.1(10) . . . . ?
C34 N4 C27 C26 179.8(6) . . . . ?
C34 N4 C28 C29 -0.8(11) . . . . ?
C34 N4 C28 C33 176.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.322
_oxdiff_exptl_absorpt_empirical_full_min 0.491
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-ab-183a
_audit_block_doi                 10.5517/ccdc.csd.cc2fpr74
_database_code_depnum_ccdc_archive 'CCDC 2255226'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c03131 2023
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;The University of Texas at Austin
United States of America
;
_audit_update_record             
;
2023-08-17 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'spiroindimicin F'
_chemical_formula_moiety         'C23 H18 Cl N3 O2'
_chemical_formula_sum            'C23 H18 Cl N3 O2'
_chemical_formula_weight         403.85
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.26480(10)
_cell_length_b                   14.87010(10)
_cell_length_c                   12.73740(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.8740(10)
_cell_angle_gamma                90
_cell_volume                     1925.89(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22973
_cell_measurement_temperature    100.01(12)
_cell_measurement_theta_max      76.8160
_cell_measurement_theta_min      2.9590
_shelx_estimated_absorpt_T_max   0.813
_shelx_estimated_absorpt_T_min   0.672
_exptl_absorpt_coefficient_mu    1.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -3 6 0.0705
2 -3 -8 0.0888
4 2 -7 0.0972
4 6 -4 0.0969
5 1 5 0.0477
-5 -1 -5 0.0627
-1 -2 8 0.0792
1 2 -8 0.0792
3 -6 -6 0.0876
-3 -8 3 0.0995
-2 8 4 0.0716
0 -5 7 0.0753
0 5 -7 0.0753
6 -2 -3 0.0927
-4 6 -4 0.0835

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.2584 -3.2059 6.4037 -0.0592 0.0676 0.9960
2.1186 -3.4692 -7.5438 -0.4258 0.4993 -0.7546
4.0221 1.9153 -7.0059 -0.0441 0.0533 -0.9976
4.3650 6.0785 -4.1613 0.3117 -0.3631 -0.8781
4.6281 0.9241 5.0536 -0.2322 -0.9701 0.0707
-4.6281 -0.9241 -5.0536 0.2322 0.9701 -0.0707
-1.0009 -1.9978 7.9963 -0.1611 -0.4734 0.8535
1.0009 1.9978 -7.9963 0.1611 0.4734 -0.8535
3.0011 -5.9975 -5.9956 -0.7269 0.3601 -0.6164
-2.9970 -7.9981 3.0003 -0.5739 0.3701 0.7174
-2.0017 7.9969 3.9962 0.8602 -0.3784 0.3047
-0.0005 -4.9964 6.9975 -0.5019 -0.4008 0.7649
0.0005 4.9964 -6.9975 0.5019 0.4008 -0.7649
5.9977 -1.9964 -2.9981 -0.5563 -0.3634 -0.6858
-3.9981 5.9944 -3.9992 0.8369 0.5726 -0.2085

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0067
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.999
_diffrn_reflns_theta_min         4.596
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00   3.00   0.50    6.50    --  -47.20 105.00  29.00  168
  2  ω     18.00  83.00   0.50    6.50    --   47.20-105.00 -69.00  130
  3  ω     37.00 107.00   0.50   26.00    --  107.75-105.00 -69.00  140
  4  ω    105.00 178.00   0.50   26.00    --  107.75 105.00  29.00  146
  5  ω   -120.00 -32.00   0.50    6.50    --  -47.20 -57.00 -90.00  176
  6  ω    -86.00 -13.00   0.50    6.50    --  -47.20 125.00  60.00  146
  7  ω    -60.00  26.00   0.50    6.50    --  -47.20  38.00  30.00  172
  8  ω     35.00 123.00   0.50   26.00    --  107.75 -57.00 -60.00  176
  9  ω     95.00 178.00   0.50   26.00    --  107.75  38.00-180.00  166
 10  ω     95.00 178.00   0.50   26.00    --  107.75  19.00  30.00  166
 11  ω     38.00 112.00   0.50   26.00    --  107.75-125.00-120.00  148
 12  ω     37.00 106.00   0.50   26.00    --  107.75 -99.00  60.00  138
 13  ω     35.00 120.00   0.50   26.00    --  107.75 -38.00-120.00  170
 14  ω     95.00 178.00   0.50   26.00    --  107.75  38.00  90.00  166
 15  ω     38.00 112.00   0.50   26.00    --  107.75-125.00  90.00  148
 16  ω     35.00 123.00   0.50   26.00    --  107.75 -57.00  60.00  176
 17  ω   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00  30.00  192
 18  ω   -120.00 -32.00   0.50    6.50    --  -47.20 -57.00  60.00  176
 19  ω   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00 150.00  192
 20  ω   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00 -30.00  192
 21  ω   -120.00 -24.00   0.50    6.50    --  -47.20 -77.00-120.00  192
 22  ω     95.00 178.00   0.50   26.00    --  107.75  19.00-120.00  166
 23  ω     95.00 178.00   0.50   26.00    --  107.75  19.00 -60.00  166
 24  ω     95.00 178.00   0.50   26.00    --  107.75  38.00 -30.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0638299000
_diffrn_orient_matrix_UB_12      0.0939262000
_diffrn_orient_matrix_UB_13      -0.0046709000
_diffrn_orient_matrix_UB_21      -0.1131250000
_diffrn_orient_matrix_UB_22      -0.0346492000
_diffrn_orient_matrix_UB_23      -0.0820224000
_diffrn_orient_matrix_UB_31      -0.0780436000
_diffrn_orient_matrix_UB_32      -0.0265727000
_diffrn_orient_matrix_UB_33      0.0903257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3942
_reflns_number_total             3983
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+1.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0895
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C9(H9), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_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 0.47477(4) 0.78976(2) 0.24602(3) 0.03653(12) Uani 1 1 d . . . . .
O1 O 0.63629(9) 0.10135(6) 0.14204(8) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.75756(9) 0.12540(6) 0.01025(7) 0.0283(2) Uani 1 1 d . . . . .
N1 N 0.43298(10) 0.41042(7) 0.35999(8) 0.0203(2) Uani 1 1 d . . . . .
N2 N 0.70966(11) 0.31295(7) 0.02686(9) 0.0240(2) Uani 1 1 d . . . . .
N3 N 0.41035(10) 0.16481(7) 0.34700(8) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.43616(11) 0.50247(8) 0.34522(9) 0.0196(2) Uani 1 1 d . . . . .
C2 C 0.38953(12) 0.57066(9) 0.40517(10) 0.0225(3) Uani 1 1 d . . . . .
H2A H 0.347162 0.557145 0.465068 0.027 Uiso 1 1 calc R U . . .
C3 C 0.40684(12) 0.65859(9) 0.37476(10) 0.0226(3) Uani 1 1 d . . . . .
H3 H 0.378040 0.706691 0.414950 0.027 Uiso 1 1 calc R U . . .
C4 C 0.46681(13) 0.67681(9) 0.28477(11) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.51508(12) 0.61113(9) 0.22471(10) 0.0228(3) Uani 1 1 d . . . . .
H5 H 0.556396 0.625975 0.164664 0.027 Uiso 1 1 calc R U . . .
C6 C 0.50112(12) 0.52103(8) 0.25536(9) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.53739(11) 0.43527(8) 0.21793(9) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.60569(12) 0.38726(8) 0.14119(10) 0.0197(2) Uani 1 1 d . . . . .
C9 C 0.67300(13) 0.39706(9) 0.05571(10) 0.0242(3) Uani 1 1 d . . . . .
H9 H 0.690858 0.452123 0.022650 0.029 Uiso 1 1 calc R U . . .
C10 C 0.66642(12) 0.24879(8) 0.09242(9) 0.0201(2) Uani 1 1 d . . . . .
C11 C 0.60071(11) 0.29389(8) 0.16427(9) 0.0182(2) Uani 1 1 d . . . . .
C12 C 0.53059(11) 0.27545(8) 0.26001(9) 0.0181(2) Uani 1 1 d . . . . .
C13 C 0.49498(11) 0.37164(8) 0.28354(9) 0.0187(2) Uani 1 1 d . . . . .
C14 C 0.69344(12) 0.15408(8) 0.07603(10) 0.0213(2) Uani 1 1 d . . . . .
C15 C 0.65577(15) 0.00570(9) 0.13091(13) 0.0333(3) Uani 1 1 d . . . . .
H15A H 0.616543 -0.013589 0.060005 0.050 Uiso 1 1 calc R U . . .
H15B H 0.613792 -0.026556 0.184407 0.050 Uiso 1 1 calc R U . . .
H15C H 0.750165 -0.007592 0.140776 0.050 Uiso 1 1 calc R U . . .
C16 C 0.61514(12) 0.23199(8) 0.35366(9) 0.0185(2) Uani 1 1 d . . . . .
C17 C 0.74456(12) 0.24842(9) 0.39423(10) 0.0219(3) Uani 1 1 d . . . . .
H17 H 0.794379 0.292311 0.362910 0.026 Uiso 1 1 calc R U . . .
C18 C 0.80095(13) 0.19905(9) 0.48252(10) 0.0249(3) Uani 1 1 d . . . . .
H18 H 0.890358 0.208657 0.510912 0.030 Uiso 1 1 calc R U . . .
C19 C 0.72682(13) 0.13628(8) 0.52858(10) 0.0250(3) Uani 1 1 d . . . . .
H19 H 0.766329 0.103206 0.588415 0.030 Uiso 1 1 calc R U . . .
C20 C 0.59479(13) 0.12057(8) 0.48876(10) 0.0233(3) Uani 1 1 d . . . . .
H20 H 0.543829 0.078260 0.521451 0.028 Uiso 1 1 calc R U . . .
C21 C 0.54042(12) 0.16894(8) 0.39963(9) 0.0189(2) Uani 1 1 d . . . . .
C22 C 0.41083(12) 0.21065(8) 0.24359(10) 0.0199(2) Uani 1 1 d . . . . .
H22A H 0.328139 0.244586 0.223808 0.024 Uiso 1 1 calc R U . . .
H22B H 0.420569 0.166418 0.187095 0.024 Uiso 1 1 calc R U . . .
C23 C 0.35055(13) 0.07559(8) 0.33674(10) 0.0235(3) Uani 1 1 d . . . . .
H23A H 0.399877 0.037427 0.293355 0.035 Uiso 1 1 calc R U . . .
H23B H 0.259236 0.080745 0.302797 0.035 Uiso 1 1 calc R U . . .
H23C H 0.352417 0.048714 0.407181 0.035 Uiso 1 1 calc R U . . .
H2 H 0.7523(17) 0.3014(12) -0.0239(15) 0.033(4) Uiso 1 1 d . . . . .
H1 H 0.3970(17) 0.3841(12) 0.4061(14) 0.034(5) 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
Cl1 C4 1.7557(13) . ?
O1 C14 1.3420(15) . ?
O1 C15 1.4460(16) . ?
O2 C14 1.2117(15) . ?
N1 C1 1.3827(16) . ?
N1 C13 1.3622(16) . ?
N1 H1 0.834(19) . ?
N2 C9 1.3707(16) . ?
N2 C10 1.3807(16) . ?
N2 H2 0.846(19) . ?
N3 C21 1.4109(15) . ?
N3 C22 1.4837(15) . ?
N3 C23 1.4602(15) . ?
C1 C2 1.3930(17) . ?
C1 C6 1.4282(16) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3821(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3998(18) . ?
C4 C5 1.3741(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4083(17) . ?
C6 C7 1.4286(17) . ?
C7 C8 1.4643(17) . ?
C7 C13 1.3721(17) . ?
C8 C9 1.3749(17) . ?
C8 C11 1.4216(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3825(17) . ?
C10 C14 1.4559(17) . ?
C11 C12 1.5235(16) . ?
C12 C13 1.5164(16) . ?
C12 C16 1.5199(16) . ?
C12 C22 1.5534(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3797(17) . ?
C16 C21 1.3904(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.4001(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.4001(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3943(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 C15 115.79(10) . . ?
C1 N1 H1 125.6(12) . . ?
C13 N1 C1 107.44(10) . . ?
C13 N1 H1 126.9(12) . . ?
C9 N2 C10 110.22(10) . . ?
C9 N2 H2 125.5(12) . . ?
C10 N2 H2 124.3(12) . . ?
C21 N3 C22 106.49(9) . . ?
C21 N3 C23 116.16(10) . . ?
C23 N3 C22 112.98(10) . . ?
N1 C1 C2 129.02(11) . . ?
N1 C1 C6 108.83(10) . . ?
C2 C1 C6 122.13(11) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 117.90(11) . . ?
C3 C2 H2A 121.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.03(11) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 Cl1 117.25(10) . . ?
C5 C4 Cl1 119.29(10) . . ?
C5 C4 C3 123.42(12) . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.63(12) . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C7 105.46(10) . . ?
C5 C6 C1 118.84(11) . . ?
C5 C6 C7 135.70(11) . . ?
C6 C7 C8 145.94(11) . . ?
C13 C7 C6 107.06(10) . . ?
C13 C7 C8 106.93(10) . . ?
C9 C8 C7 144.63(12) . . ?
C9 C8 C11 107.66(11) . . ?
C11 C8 C7 107.71(10) . . ?
N2 C9 C8 107.57(11) . . ?
N2 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
N2 C10 C11 106.95(11) . . ?
N2 C10 C14 119.90(11) . . ?
C11 C10 C14 133.15(11) . . ?
C8 C11 C12 112.06(10) . . ?
C10 C11 C8 107.60(10) . . ?
C10 C11 C12 140.31(11) . . ?
C11 C12 C22 117.12(10) . . ?
C13 C12 C11 98.14(9) . . ?
C13 C12 C16 111.91(9) . . ?
C13 C12 C22 113.83(10) . . ?
C16 C12 C11 115.03(10) . . ?
C16 C12 C22 101.43(9) . . ?
N1 C13 C7 111.21(11) . . ?
N1 C13 C12 133.59(11) . . ?
C7 C13 C12 115.14(10) . . ?
O1 C14 C10 111.54(10) . . ?
O2 C14 O1 123.58(12) . . ?
O2 C14 C10 124.87(12) . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C12 129.47(11) . . ?
C17 C16 C21 121.34(11) . . ?
C21 C16 C12 109.18(10) . . ?
C16 C17 H17 120.7 . . ?
C16 C17 C18 118.61(12) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.21(12) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.33(12) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 121.0 . . ?
C21 C20 C19 117.94(12) . . ?
C21 C20 H20 121.0 . . ?
C16 C21 N3 111.71(10) . . ?
C16 C21 C20 120.56(11) . . ?
C20 C21 N3 127.70(11) . . ?
N3 C22 C12 105.32(9) . . ?
N3 C22 H22A 110.7 . . ?
N3 C22 H22B 110.7 . . ?
C12 C22 H22A 110.7 . . ?
C12 C22 H22B 110.7 . . ?
H22A C22 H22B 108.8 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
Cl1 C4 C5 C6 -176.95(9) . . . . ?
N1 C1 C2 C3 178.81(12) . . . . ?
N1 C1 C6 C5 179.56(11) . . . . ?
N1 C1 C6 C7 -0.46(13) . . . . ?
N2 C10 C11 C8 -0.33(13) . . . . ?
N2 C10 C11 C12 -177.66(14) . . . . ?
N2 C10 C14 O1 -175.62(11) . . . . ?
N2 C10 C14 O2 3.29(19) . . . . ?
C1 N1 C13 C7 -0.82(14) . . . . ?
C1 N1 C13 C12 176.13(12) . . . . ?
C1 C2 C3 C4 1.49(18) . . . . ?
C1 C6 C7 C8 -176.24(17) . . . . ?
C1 C6 C7 C13 -0.03(13) . . . . ?
C2 C1 C6 C5 -1.83(18) . . . . ?
C2 C1 C6 C7 178.14(11) . . . . ?
C2 C3 C4 Cl1 175.63(10) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C4 C5 C6 C1 1.07(18) . . . . ?
C4 C5 C6 C7 -178.89(13) . . . . ?
C5 C6 C7 C8 3.7(3) . . . . ?
C5 C6 C7 C13 179.94(14) . . . . ?
C6 C1 C2 C3 0.51(18) . . . . ?
C6 C7 C8 C9 -3.3(3) . . . . ?
C6 C7 C8 C11 176.53(17) . . . . ?
C6 C7 C13 N1 0.53(14) . . . . ?
C6 C7 C13 C12 -177.04(10) . . . . ?
C7 C8 C9 N2 179.36(16) . . . . ?
C7 C8 C11 C10 -179.39(10) . . . . ?
C7 C8 C11 C12 -1.23(13) . . . . ?
C8 C7 C13 N1 178.31(10) . . . . ?
C8 C7 C13 C12 0.75(14) . . . . ?
C8 C11 C12 C13 1.52(12) . . . . ?
C8 C11 C12 C16 -117.35(11) . . . . ?
C8 C11 C12 C22 123.64(11) . . . . ?
C9 N2 C10 C11 0.07(14) . . . . ?
C9 N2 C10 C14 179.58(11) . . . . ?
C9 C8 C11 C10 0.48(14) . . . . ?
C9 C8 C11 C12 178.64(10) . . . . ?
C10 N2 C9 C8 0.23(15) . . . . ?
C10 C11 C12 C13 178.77(15) . . . . ?
C10 C11 C12 C16 59.9(2) . . . . ?
C10 C11 C12 C22 -59.1(2) . . . . ?
C11 C8 C9 N2 -0.43(14) . . . . ?
C11 C10 C14 O1 3.73(19) . . . . ?
C11 C10 C14 O2 -177.35(13) . . . . ?
C11 C12 C13 N1 -178.23(13) . . . . ?
C11 C12 C13 C7 -1.37(13) . . . . ?
C11 C12 C16 C17 39.81(17) . . . . ?
C11 C12 C16 C21 -141.29(11) . . . . ?
C11 C12 C22 N3 148.54(10) . . . . ?
C12 C16 C17 C18 179.77(11) . . . . ?
C12 C16 C21 N3 -0.50(13) . . . . ?
C12 C16 C21 C20 -178.81(11) . . . . ?
C13 N1 C1 C2 -177.70(12) . . . . ?
C13 N1 C1 C6 0.78(13) . . . . ?
C13 C7 C8 C9 -179.48(18) . . . . ?
C13 C7 C8 C11 0.31(13) . . . . ?
C13 C12 C16 C17 -71.06(16) . . . . ?
C13 C12 C16 C21 107.84(11) . . . . ?
C13 C12 C22 N3 -97.87(11) . . . . ?
C14 C10 C11 C8 -179.75(13) . . . . ?
C14 C10 C11 C12 2.9(3) . . . . ?
C15 O1 C14 O2 0.20(18) . . . . ?
C15 O1 C14 C10 179.14(11) . . . . ?
C16 C12 C13 N1 -57.02(17) . . . . ?
C16 C12 C13 C7 119.84(11) . . . . ?
C16 C12 C22 N3 22.49(11) . . . . ?
C16 C17 C18 C19 -1.05(18) . . . . ?
C17 C16 C21 N3 178.51(11) . . . . ?
C17 C16 C21 C20 0.19(18) . . . . ?
C17 C18 C19 C20 -0.06(19) . . . . ?
C18 C19 C20 C21 1.22(19) . . . . ?
C19 C20 C21 N3 -179.31(11) . . . . ?
C19 C20 C21 C16 -1.28(18) . . . . ?
C21 N3 C22 C12 -23.84(12) . . . . ?
C21 C16 C17 C18 0.99(18) . . . . ?
C22 N3 C21 C16 15.67(13) . . . . ?
C22 N3 C21 C20 -166.16(12) . . . . ?
C22 C12 C13 N1 57.26(17) . . . . ?
C22 C12 C13 C7 -125.88(11) . . . . ?
C22 C12 C16 C17 167.23(12) . . . . ?
C22 C12 C16 C21 -13.87(12) . . . . ?
C23 N3 C21 C16 142.46(11) . . . . ?
C23 N3 C21 C20 -39.36(17) . . . . ?
C23 N3 C22 C12 -152.52(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.840
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane, methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-ab-158a
_audit_block_doi                 10.5517/ccdc.csd.cc2g0whw
_database_code_depnum_ccdc_archive 'CCDC 2264968'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c03131 2023
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2023-05-23 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2023-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br Cl N2 O4'
_chemical_formula_sum            'C15 H12 Br Cl N2 O4'
_chemical_formula_weight         399.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H12N2O4ClBr
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1305(3)
_cell_length_b                   9.5099(3)
_cell_length_c                   9.6003(4)
_cell_angle_alpha                73.634(4)
_cell_angle_beta                 81.798(3)
_cell_angle_gamma                72.598(3)
_cell_volume                     761.66(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12449
_cell_measurement_temperature    100.02(14)
_cell_measurement_theta_max      76.6350
_cell_measurement_theta_min      4.8100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.503
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56807
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 -5 0.0614
-1 4 -2 0.1184
1 6 0 0.1244
3 6 2 0.1394
4 0 5 0.0552
-4 -5 0 0.1405
1 -5 -4 0.1198
2 -3 -5 0.1208
4 5 -1 0.1385
0 5 4 0.1173
-4 0 4 0.1068
4 -1 4 0.0477
6 2 2 0.0970
-6 -2 -2 0.0970
5 -2 2 0.0675
-5 2 -2 0.0755

_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.4312 -2.0147 -4.7431 -0.6766 0.6407 0.3630
-1.1393 4.3273 -2.3638 -0.5310 0.5044 -0.6809
1.1144 5.8806 -0.0764 -0.2259 0.2155 -0.9500
3.1377 5.9501 2.2902 0.1457 -0.1366 -0.9798
3.9488 0.1452 4.6166 0.7245 -0.6867 -0.0598
-3.5503 -5.3506 0.4257 0.2925 0.2488 0.9234
0.9674 -4.6170 -4.2944 -0.5708 -0.4890 0.6595
2.4529 -2.7022 -4.6954 -0.7194 -0.6156 0.3218
3.6904 5.1346 -0.7363 -0.3385 -0.2882 -0.8957
-0.4043 5.1298 3.9959 0.4973 0.4263 -0.7556
-3.6360 0.1721 4.3234 0.7564 0.6467 0.0979
4.0080 -0.7352 3.9848 0.6483 -0.7581 0.0707
5.7542 1.9025 2.3174 0.2604 -0.8788 -0.3999
-5.7542 -1.9025 -2.3174 -0.2604 0.8788 0.3999
4.7610 -1.5636 1.6682 0.2811 -0.9462 0.1600
-4.7610 1.5636 -1.6682 -0.2811 0.9462 -0.1600

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12747
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.971
_diffrn_reflns_theta_min         4.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.02(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -61.00   0.50    4.50    --  -47.07-143.00 -25.00  116
  2  ω    -99.00 -22.00   0.50    4.50    --  -47.07 143.00  28.00  154
  3  ω    -88.00 -14.00   0.50    4.50    --  -47.07 127.00-140.00  148
  4  ω   -119.00 -72.00   0.50    4.50    --  -47.07-127.00 143.00   94
  5  ω     36.00  96.00   0.50    4.50    --   47.07-127.00 143.00  120
  6  ω     44.00 105.00   0.50    4.50    --   47.07-143.00 -25.00  122
  7  ω     83.00 171.00   0.50   18.00    --  107.75 143.00  28.00  176
  8  ω     36.00 113.00   0.50   18.00    --  107.75-127.00 143.00  154
  9  ω     44.00 125.00   0.50   18.00    --  107.75-143.00 -25.00  162
 10  ω     94.00 178.00   0.50   18.00    --  107.75 127.00-140.00  168
 11  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 -30.00  190
 12  ω   -121.00 -34.00   0.50    4.50    --  -47.07 -19.00   0.00  174
 13  ω   -119.00 -73.00   0.50    4.50    --  -47.07-125.00   0.00   92
 14  ω     35.00 120.00   0.50   18.00    --  107.75 -38.00 120.00  170
 15  ω     85.00 178.00   0.50   18.00    --  107.75  77.00  30.00  186
 16  ω     35.00 120.00   0.50   18.00    --  107.75 -38.00 -90.00  170
 17  ω     35.00 106.00   0.50   18.00    --  107.75 -99.00 120.00  142
 18  ω     35.00 106.00   0.50   18.00    --  107.75 -99.00-150.00  142
 19  ω     35.00 106.00   0.50   18.00    --  107.75 -99.00 150.00  142
 20  ω     35.00 106.00   0.50   18.00    --  107.75 -99.00 -60.00  142
 21  ω     93.00 178.00   0.50   18.00    --  107.75  57.00-150.00  170
 22  ω     95.00 178.00   0.50   18.00    --  107.75  38.00 -60.00  166
 23  ω     35.00 106.00   0.50   18.00    --  107.75 -99.00  30.00  142
 24  ω     35.00 123.00   0.50   18.00    --  107.75 -57.00 -60.00  176
 25  ω     95.00 178.00   0.50   18.00    --  107.75  38.00 -30.00  166
 26  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00-150.00  190
 27  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 120.00  190
 28  ω   -118.00 -32.00   0.50    4.50    --  -47.07 -57.00-120.00  172
 29  ω   -118.00 -32.00   0.50    4.50    --  -47.07 -57.00 150.00  172
 30  ω   -119.00 -73.00   0.50    4.50    --  -47.07-125.00-180.00   92
 31  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00  90.00  190
 32  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00 -60.00  190
 33  ω   -119.00 -24.00   0.50    4.50    --  -47.07 -77.00  30.00  190
 34  ω     95.00 178.00   0.50   18.00    --  107.75  38.00  90.00  166
 35  ω     95.00 178.00   0.50   18.00    --  107.75  19.00 150.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0107940000
_diffrn_orient_matrix_UB_12      -0.0341925000
_diffrn_orient_matrix_UB_13      0.1672482000
_diffrn_orient_matrix_UB_21      -0.1755099000
_diffrn_orient_matrix_UB_22      0.0699013000
_diffrn_orient_matrix_UB_23      -0.0008109000
_diffrn_orient_matrix_UB_31      -0.0217618000
_diffrn_orient_matrix_UB_32      -0.1572873000
_diffrn_orient_matrix_UB_33      0.0106159000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3096
_reflns_number_total             3097
_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 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0237
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.8078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0620
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C11(H11)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57881(2) 0.43277(2) 0.69372(2) 0.01798(7) Uani 1 1 d . . . . .
Cl1 Cl 1.24390(6) 0.33508(6) 0.69169(6) 0.03054(12) Uani 1 1 d . . . . .
O1 O 0.61023(15) -0.00935(15) 0.65784(13) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.88510(15) -0.09443(14) 0.83711(14) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.835(3) -0.144(3) 0.840(3) 0.025(7) Uiso 1 1 d . . . . .
O3 O 0.24829(15) 0.33436(15) 1.12015(14) 0.0213(3) Uani 1 1 d . . . . .
O4 O 0.31718(14) 0.51944(14) 0.94350(14) 0.0181(3) Uani 1 1 d . . . . .
N1 N 0.77126(17) 0.12652(17) 0.51674(16) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.53252(17) 0.13336(17) 1.08097(17) 0.0156(3) Uani 1 1 d . . . . .
H2A H 0.493(3) 0.105(3) 1.157(3) 0.025(6) Uiso 1 1 d . . . . .
C1 C 0.7126(2) 0.05303(19) 0.64422(19) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.80027(19) 0.05678(19) 0.77073(18) 0.0148(3) Uani 1 1 d . . . . .
C3 C 0.91037(19) 0.14694(19) 0.68791(19) 0.0156(3) Uani 1 1 d . . . . .
C4 C 1.0185(2) 0.1927(2) 0.7378(2) 0.0178(3) Uani 1 1 d . . . . .
H4 H 1.032768 0.169478 0.838713 0.021 Uiso 1 1 calc R U . . .
C5 C 1.1060(2) 0.2747(2) 0.6338(2) 0.0208(4) Uani 1 1 d . . . . .
C6 C 1.0874(2) 0.3094(2) 0.4859(2) 0.0225(4) Uani 1 1 d . . . . .
H6 H 1.149927 0.364375 0.418313 0.027 Uiso 1 1 calc R U . . .
C7 C 0.9769(2) 0.2638(2) 0.4363(2) 0.0204(4) Uani 1 1 d . . . . .
H7 H 0.961971 0.287389 0.335511 0.024 Uiso 1 1 calc R U . . .
C8 C 0.8900(2) 0.1830(2) 0.5396(2) 0.0171(3) Uani 1 1 d . . . . .
C9 C 0.7159(2) 0.1457(2) 0.37596(19) 0.0210(4) Uani 1 1 d . . . . .
H9A H 0.800639 0.099630 0.313715 0.031 Uiso 1 1 calc R U . . .
H9B H 0.676388 0.254515 0.330051 0.031 Uiso 1 1 calc R U . . .
H9C H 0.633406 0.095851 0.389275 0.031 Uiso 1 1 calc R U . . .
C10 C 0.68800(19) 0.12519(19) 0.88085(19) 0.0149(3) Uani 1 1 d . . . . .
C11 C 0.65321(19) 0.04445(19) 1.01943(19) 0.0157(3) Uani 1 1 d . . . . .
H11 H 0.705991 -0.057549 1.064219 0.019 Uiso 1 1 calc R U . . .
C12 C 0.4845(2) 0.27347(19) 0.98570(19) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.58204(19) 0.27143(19) 0.86116(18) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.3400(2) 0.3770(2) 1.02405(19) 0.0161(3) Uani 1 1 d . . . . .
C15 C 0.1711(2) 0.6215(2) 0.9768(2) 0.0216(4) Uani 1 1 d . . . . .
H15A H 0.156241 0.610573 1.082027 0.032 Uiso 1 1 calc R U . . .
H15B H 0.087651 0.596215 0.943843 0.032 Uiso 1 1 calc R U . . .
H15C H 0.170788 0.726846 0.926926 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.8803(17) . ?
Cl1 C5 1.7422(19) . ?
O1 C1 1.223(2) . ?
O2 H2 0.74(3) . ?
O2 C2 1.426(2) . ?
O3 C14 1.220(2) . ?
O4 C14 1.328(2) . ?
O4 C15 1.450(2) . ?
N1 C1 1.352(2) . ?
N1 C8 1.413(2) . ?
N1 C9 1.455(2) . ?
N2 H2A 0.78(3) . ?
N2 C11 1.348(2) . ?
N2 C12 1.372(2) . ?
C1 C2 1.561(2) . ?
C2 C3 1.510(2) . ?
C2 C10 1.507(2) . ?
C3 C4 1.380(2) . ?
C3 C8 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(3) . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.382(2) . ?
C10 C13 1.416(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(2) . ?
C12 C14 1.461(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C2 O2 H2 106(2) . . ?
C14 O4 C15 114.33(14) . . ?
C1 N1 C8 111.01(14) . . ?
C1 N1 C9 123.68(15) . . ?
C8 N1 C9 125.30(15) . . ?
C11 N2 H2A 123.5(19) . . ?
C11 N2 C12 109.93(15) . . ?
C12 N2 H2A 126.4(19) . . ?
O1 C1 N1 125.57(16) . . ?
O1 C1 C2 125.59(16) . . ?
N1 C1 C2 108.81(14) . . ?
O2 C2 C1 109.10(14) . . ?
O2 C2 C3 109.40(14) . . ?
O2 C2 C10 110.49(14) . . ?
C3 C2 C1 101.10(13) . . ?
C10 C2 C1 110.10(13) . . ?
C10 C2 C3 116.15(14) . . ?
C4 C3 C2 130.16(16) . . ?
C4 C3 C8 120.67(16) . . ?
C8 C3 C2 109.17(15) . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.23(17) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 Cl1 118.88(15) . . ?
C6 C5 Cl1 118.80(14) . . ?
C6 C5 C4 122.31(17) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.16(17) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.40(17) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 N1 109.87(15) . . ?
C7 C8 N1 127.90(17) . . ?
C7 C8 C3 122.22(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 124.47(15) . . ?
C11 C10 C13 105.86(15) . . ?
C13 C10 C2 129.01(15) . . ?
N2 C11 C10 109.21(15) . . ?
N2 C11 H11 125.4 . . ?
C10 C11 H11 125.4 . . ?
N2 C12 C13 106.78(15) . . ?
N2 C12 C14 117.72(15) . . ?
C13 C12 C14 134.77(16) . . ?
C10 C13 Br1 124.84(13) . . ?
C12 C13 Br1 126.96(13) . . ?
C12 C13 C10 108.20(15) . . ?
O3 C14 O4 123.62(16) . . ?
O3 C14 C12 122.39(16) . . ?
O4 C14 C12 113.97(15) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C5 C6 C7 -179.41(15) . . . . ?
O1 C1 C2 O2 64.4(2) . . . . ?
O1 C1 C2 C3 179.63(16) . . . . ?
O1 C1 C2 C10 -57.0(2) . . . . ?
O2 C2 C3 C4 -66.4(2) . . . . ?
O2 C2 C3 C8 113.45(16) . . . . ?
O2 C2 C10 C11 -10.4(2) . . . . ?
O2 C2 C10 C13 -179.81(16) . . . . ?
N1 C1 C2 O2 -113.98(15) . . . . ?
N1 C1 C2 C3 1.24(17) . . . . ?
N1 C1 C2 C10 124.61(15) . . . . ?
N2 C12 C13 Br1 -177.83(12) . . . . ?
N2 C12 C13 C10 1.74(19) . . . . ?
N2 C12 C14 O3 -14.3(3) . . . . ?
N2 C12 C14 O4 166.78(15) . . . . ?
C1 N1 C8 C3 -0.5(2) . . . . ?
C1 N1 C8 C7 -179.98(17) . . . . ?
C1 C2 C3 C4 178.62(17) . . . . ?
C1 C2 C3 C8 -1.55(17) . . . . ?
C1 C2 C10 C11 110.15(18) . . . . ?
C1 C2 C10 C13 -59.2(2) . . . . ?
C2 C3 C4 C5 179.32(17) . . . . ?
C2 C3 C8 N1 1.38(19) . . . . ?
C2 C3 C8 C7 -179.14(16) . . . . ?
C2 C10 C11 N2 -170.57(15) . . . . ?
C2 C10 C13 Br1 -11.1(3) . . . . ?
C2 C10 C13 C12 169.30(16) . . . . ?
C3 C2 C10 C11 -135.77(17) . . . . ?
C3 C2 C10 C13 54.8(2) . . . . ?
C3 C4 C5 Cl1 179.95(13) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C3 C8 N1 -178.77(15) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 N1 179.21(17) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C8 N1 C1 O1 -178.89(16) . . . . ?
C8 N1 C1 C2 -0.51(19) . . . . ?
C8 C3 C4 C5 -0.5(3) . . . . ?
C9 N1 C1 O1 2.0(3) . . . . ?
C9 N1 C1 C2 -179.61(15) . . . . ?
C9 N1 C8 C3 178.54(16) . . . . ?
C9 N1 C8 C7 -0.9(3) . . . . ?
C10 C2 C3 C4 59.5(2) . . . . ?
C10 C2 C3 C8 -120.66(16) . . . . ?
C11 N2 C12 C13 -1.22(19) . . . . ?
C11 N2 C12 C14 170.46(14) . . . . ?
C11 C10 C13 Br1 177.97(12) . . . . ?
C11 C10 C13 C12 -1.61(19) . . . . ?
C12 N2 C11 C10 0.20(19) . . . . ?
C13 C10 C11 N2 0.87(19) . . . . ?
C13 C12 C14 O3 154.40(19) . . . . ?
C13 C12 C14 O4 -24.5(3) . . . . ?
C14 C12 C13 Br1 12.6(3) . . . . ?
C14 C12 C13 C10 -167.86(18) . . . . ?
C15 O4 C14 O3 -1.3(2) . . . . ?
C15 O4 C14 C12 177.55(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.833
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1-ab-101b-1vl
_audit_block_doi                 10.5517/ccdc.csd.cc2fhxd8
_database_code_depnum_ccdc_archive 'CCDC 2249620'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.3c03131 2023
loop_
_audit_author_name
_audit_author_address
'Vincent Lynch'
;University of Texas at Austin
United States of America
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
_audit_creation_date             2022-11-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12 Br Cl N2 O4'
_chemical_formula_sum            'C15 H12 Br Cl N2 O4'
_chemical_formula_weight         399.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H12 N2 O4 Cl Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.45120(10)
_cell_length_b                   8.02230(10)
_cell_length_c                   14.9534(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.1410(10)
_cell_angle_gamma                90
_cell_volume                     1564.72(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20055
_cell_measurement_temperature    100.1(4)
_cell_measurement_theta_max      76.8570
_cell_measurement_theta_min      3.0670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.358
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.299
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 5 -5 0.1111
-3 -1 9 0.0946
0 -5 2 0.1236
8 -1 0 0.0590
-8 1 0 0.0840
-2 1 9 0.1102
4 0 -9 0.0832
-4 0 9 0.0932
2 -5 -4 0.1359
-4 -1 -7 0.1112
-3 5 3 0.1436
-6 0 -5 0.0936
6 0 5 0.0896

_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.5604 4.5665 -4.6311 0.8334 -0.5097 0.2135
-3.4910 -0.7112 9.4777 -0.3333 0.2027 -0.9208
0.4963 -5.0311 2.2372 -0.8516 0.5212 0.0552
8.4399 -0.5516 -0.0751 0.3220 0.9119 0.2544
-8.4399 0.5516 0.0751 -0.3220 -0.9119 -0.2544
-2.0001 1.0000 9.0003 0.0372 0.2135 -0.9220
4.0001 -0.0000 -9.0002 0.2340 -0.0746 0.9253
-4.0001 0.0000 9.0002 -0.2340 0.0746 -0.9253
1.9996 -5.0000 -3.9994 -0.7468 0.3354 0.6617
-3.9996 -1.0001 -7.0008 -0.3415 -0.7286 0.5829
-2.9996 4.9999 2.9992 0.7014 -0.4940 -0.5966
-5.9995 -0.0001 -5.0010 -0.2760 -0.8967 0.2993
5.9995 0.0001 5.0010 0.2760 0.8967 -0.2993

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21679
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.235
_diffrn_reflns_theta_min         3.388
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -37.00   0.50    6.00    --  -48.82 -41.00  20.00  168
  2  ω     37.00 121.00   0.50    6.00    --   48.82  41.00 173.00  168
  3  ω    -23.00  61.00   0.50    6.00    --   48.82 -41.00  20.00  168
  4  ω     35.00 120.00   0.50   24.00    --  107.75 -41.00  20.00  170
  5  ω     96.00 178.00   0.50   24.00    --  107.75  41.00 173.00  164
  6  ω    -61.00  24.00   0.50    6.00    --  -48.82  41.00 173.00  170
  7  ω     34.00  97.00   0.50    6.00    --   48.82-125.00-120.00  126
  8  ω     34.00  97.00   0.50    6.00    --   48.82-125.00  60.00  126
  9  ω     35.00 123.00   0.50   24.00    --  107.75 -57.00 150.00  176
 10  ω     32.00 121.00   0.50   24.00    --  107.75 -19.00   0.00  178
 11  ω     35.00 106.00   0.50   24.00    --  107.75 -99.00-120.00  142
 12  ω     35.00 112.00   0.50   24.00    --  107.75-125.00-180.00  154
 13  ω     35.00 106.00   0.50   24.00    --  107.75 -99.00  30.00  142
 14  ω     95.00 178.00   0.50   24.00    --  107.75  19.00-150.00  166
 15  ω     32.00 121.00   0.50   24.00    --  107.75 -19.00-150.00  178
 16  ω     35.00 112.00   0.50   24.00    --  107.75-125.00  30.00  154
 17  ω     35.00 112.00   0.50   24.00    --  107.75-125.00-120.00  154
 18  ω     35.00 120.00   0.50   24.00    --  107.75 -38.00-150.00  170
 19  ω   -121.00 -34.00   0.50    6.00    --  -48.82 -57.00 -60.00  174
 20  ω   -121.00 -34.00   0.50    6.00    --  -48.82 -57.00   0.00  174
 21  ω   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00 120.00  190
 22  ω   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00-180.00  190
 23  ω   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00 -60.00  190
 24  ω   -121.00 -26.00   0.50    6.00    --  -48.82 -77.00-120.00  190
 25  ω     95.00 178.00   0.50   24.00    --  107.75  19.00  30.00  166
 26  ω     95.00 170.00   0.50   24.00    --  107.75  38.00 -60.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493815000
_diffrn_orient_matrix_UB_12      0.1723442000
_diffrn_orient_matrix_UB_13      -0.0040476000
_diffrn_orient_matrix_UB_21      0.1040185000
_diffrn_orient_matrix_UB_22      -0.0690987000
_diffrn_orient_matrix_UB_23      0.0545201000
_diffrn_orient_matrix_UB_31      0.0261264000
_diffrn_orient_matrix_UB_32      -0.0489447000
_diffrn_orient_matrix_UB_33      -0.0911992000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3238
_reflns_number_total             3240
_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 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Shelxtl-Plus, Bruker AXS, Inc. 2009'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.728
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+1.4442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0758
_refine_ls_wR_factor_ref         0.0758
_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 Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C12(H12)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_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
Br1 Br 0.29790(2) 0.20994(2) 0.58966(2) 0.02267(9) Uani 1 1 d . . . . .
Cl1 Cl 0.65565(3) 0.52298(7) 0.62617(3) 0.02987(13) Uani 1 1 d . . . . .
O1 O 0.12449(10) 0.6671(2) 0.69269(10) 0.0250(3) Uani 1 1 d . . . . .
O2 O 0.26680(11) 0.80957(16) 0.58110(10) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.08812(10) 0.87684(17) 0.46853(9) 0.0198(3) Uani 1 1 d . . . . .
O4 O -0.01891(10) 0.72785(17) 0.35874(9) 0.0209(3) Uani 1 1 d . . . . .
N1 N 0.28261(11) 0.5579(2) 0.76162(10) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.06563(12) 0.4395(2) 0.41584(10) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.21162(13) 0.6252(2) 0.69084(12) 0.0179(3) Uani 1 1 d . . . . .
C2 C 0.26005(13) 0.6411(2) 0.60568(12) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.36826(13) 0.5814(2) 0.64701(12) 0.0146(3) Uani 1 1 d . . . . .
C4 C 0.45312(13) 0.5798(2) 0.61052(12) 0.0171(3) Uani 1 1 d . . . . .
H4 H 0.449176 0.615478 0.549174 0.021 Uiso 1 1 calc R U . . .
C5 C 0.54479(13) 0.5235(2) 0.66770(13) 0.0183(4) Uani 1 1 d . . . . .
C6 C 0.55295(14) 0.4699(2) 0.75732(13) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.616431 0.428804 0.793279 0.023 Uiso 1 1 calc R U . . .
C7 C 0.46742(14) 0.4766(2) 0.79441(13) 0.0192(4) Uani 1 1 d . . . . .
H7 H 0.471379 0.442166 0.855979 0.023 Uiso 1 1 calc R U . . .
C8 C 0.37699(13) 0.5348(2) 0.73859(12) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.26663(17) 0.5258(3) 0.85288(14) 0.0291(5) Uani 1 1 d . . . . .
H9A H 0.310688 0.599673 0.897862 0.044 Uiso 1 1 calc R U . . .
H9B H 0.283756 0.409429 0.869928 0.044 Uiso 1 1 calc R U . . .
H9C H 0.194684 0.546567 0.852303 0.044 Uiso 1 1 calc R U . . .
C10 C 0.19527(13) 0.5339(2) 0.52965(11) 0.0143(3) Uani 1 1 d . . . . .
C11 C 0.10829(13) 0.5810(2) 0.46127(11) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.11982(14) 0.3044(2) 0.45181(13) 0.0177(4) Uani 1 1 d . . . . .
H12 H 0.105120 0.192216 0.432825 0.021 Uiso 1 1 calc R U . . .
C13 C 0.20062(13) 0.3585(2) 0.52127(12) 0.0164(3) Uani 1 1 d . . . . .
C14 C 0.06047(13) 0.7427(2) 0.43233(12) 0.0156(3) Uani 1 1 d . . . . .
C15 C -0.06871(16) 0.8838(3) 0.32416(14) 0.0269(4) Uani 1 1 d . . . . .
H15A H -0.127943 0.860865 0.272749 0.040 Uiso 1 1 calc R U . . .
H15B H -0.020101 0.955258 0.302798 0.040 Uiso 1 1 calc R U . . .
H15C H -0.091674 0.940406 0.373627 0.040 Uiso 1 1 calc R U . . .
H2A H 0.006(2) 0.437(3) 0.3755(19) 0.030(6) Uiso 1 1 d . . . . .
H2 H 0.214(2) 0.839(4) 0.5537(19) 0.032(7) 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
Br1 C13 1.8772(18) . ?
Cl1 C5 1.7499(18) . ?
O1 C1 1.226(2) . ?
O2 C2 1.409(2) . ?
O2 H2 0.76(3) . ?
O3 C14 1.221(2) . ?
O4 C14 1.338(2) . ?
O4 C15 1.453(2) . ?
N1 C1 1.353(2) . ?
N1 C8 1.406(2) . ?
N1 C9 1.455(2) . ?
N2 C11 1.374(2) . ?
N2 C12 1.343(2) . ?
N2 H2A 0.88(3) . ?
C1 C2 1.571(2) . ?
C2 C3 1.514(2) . ?
C2 C10 1.519(2) . ?
C3 C4 1.380(2) . ?
C3 C8 1.396(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 C6 1.386(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.404(2) . ?
C10 C13 1.417(2) . ?
C11 C14 1.465(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C2 O2 H2 109(2) . . ?
C14 O4 C15 114.95(16) . . ?
C1 N1 C8 111.59(15) . . ?
C1 N1 C9 124.51(16) . . ?
C8 N1 C9 123.72(16) . . ?
C11 N2 H2A 124.1(18) . . ?
C12 N2 C11 110.39(15) . . ?
C12 N2 H2A 124.9(18) . . ?
O1 C1 N1 126.01(17) . . ?
O1 C1 C2 125.72(17) . . ?
N1 C1 C2 108.27(14) . . ?
O2 C2 C1 110.83(15) . . ?
O2 C2 C3 107.06(14) . . ?
O2 C2 C10 114.17(14) . . ?
C3 C2 C1 101.01(13) . . ?
C3 C2 C10 116.41(15) . . ?
C10 C2 C1 106.56(13) . . ?
C4 C3 C2 130.33(16) . . ?
C4 C3 C8 120.38(16) . . ?
C8 C3 C2 109.10(15) . . ?
C3 C4 H4 121.5 . . ?
C3 C4 C5 116.99(16) . . ?
C5 C4 H4 121.5 . . ?
C4 C5 Cl1 119.10(14) . . ?
C6 C5 Cl1 117.99(14) . . ?
C6 C5 C4 122.90(17) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.62(16) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 121.2 . . ?
C8 C7 C6 117.64(17) . . ?
C8 C7 H7 121.2 . . ?
C3 C8 N1 109.89(15) . . ?
C7 C8 N1 127.76(17) . . ?
C7 C8 C3 122.35(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 128.03(16) . . ?
C11 C10 C13 104.73(15) . . ?
C13 C10 C2 126.62(16) . . ?
N2 C11 C10 108.10(16) . . ?
N2 C11 C14 119.00(15) . . ?
C10 C11 C14 132.90(16) . . ?
N2 C12 H12 126.3 . . ?
N2 C12 C13 107.40(16) . . ?
C13 C12 H12 126.3 . . ?
C10 C13 Br1 128.78(14) . . ?
C12 C13 Br1 121.85(13) . . ?
C12 C13 C10 109.37(16) . . ?
O3 C14 O4 122.56(17) . . ?
O3 C14 C11 125.80(16) . . ?
O4 C14 C11 111.64(16) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C5 C6 C7 176.75(14) . . . . ?
O1 C1 C2 O2 63.2(2) . . . . ?
O1 C1 C2 C3 176.43(18) . . . . ?
O1 C1 C2 C10 -61.5(2) . . . . ?
O2 C2 C3 C4 -57.0(2) . . . . ?
O2 C2 C3 C8 117.78(16) . . . . ?
O2 C2 C10 C11 -32.7(2) . . . . ?
O2 C2 C10 C13 157.74(17) . . . . ?
N1 C1 C2 O2 -116.58(16) . . . . ?
N1 C1 C2 C3 -3.38(18) . . . . ?
N1 C1 C2 C10 118.67(16) . . . . ?
N2 C11 C14 O3 177.30(16) . . . . ?
N2 C11 C14 O4 -3.4(2) . . . . ?
N2 C12 C13 Br1 -179.12(12) . . . . ?
N2 C12 C13 C10 1.0(2) . . . . ?
C1 N1 C8 C3 -2.8(2) . . . . ?
C1 N1 C8 C7 176.91(18) . . . . ?
C1 C2 C3 C4 -173.06(18) . . . . ?
C1 C2 C3 C8 1.76(18) . . . . ?
C1 C2 C10 C11 90.0(2) . . . . ?
C1 C2 C10 C13 -79.6(2) . . . . ?
C2 C3 C4 C5 176.98(17) . . . . ?
C2 C3 C8 N1 0.4(2) . . . . ?
C2 C3 C8 C7 -179.35(16) . . . . ?
C2 C10 C11 N2 -171.29(16) . . . . ?
C2 C10 C11 C14 9.5(3) . . . . ?
C2 C10 C13 Br1 -9.0(3) . . . . ?
C2 C10 C13 C12 170.88(16) . . . . ?
C3 C2 C10 C11 -158.28(17) . . . . ?
C3 C2 C10 C13 32.2(2) . . . . ?
C3 C4 C5 Cl1 -178.61(13) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C3 C8 N1 175.78(16) . . . . ?
C4 C3 C8 C7 -3.9(3) . . . . ?
C4 C5 C6 C7 -2.2(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 N1 -177.66(17) . . . . ?
C6 C7 C8 C3 2.0(3) . . . . ?
C8 N1 C1 O1 -175.92(18) . . . . ?
C8 N1 C1 C2 3.9(2) . . . . ?
C8 C3 C4 C5 2.7(3) . . . . ?
C9 N1 C1 O1 -0.7(3) . . . . ?
C9 N1 C1 C2 179.15(17) . . . . ?
C9 N1 C8 C3 -178.09(18) . . . . ?
C9 N1 C8 C7 1.6(3) . . . . ?
C10 C2 C3 C4 72.0(2) . . . . ?
C10 C2 C3 C8 -113.13(17) . . . . ?
C10 C11 C14 O3 -3.5(3) . . . . ?
C10 C11 C14 O4 175.76(17) . . . . ?
C11 N2 C12 C13 -1.0(2) . . . . ?
C11 C10 C13 Br1 179.48(13) . . . . ?
C11 C10 C13 C12 -0.6(2) . . . . ?
C12 N2 C11 C10 0.56(19) . . . . ?
C12 N2 C11 C14 179.93(15) . . . . ?
C13 C10 C11 N2 0.06(18) . . . . ?
C13 C10 C11 C14 -179.19(18) . . . . ?
C15 O4 C14 O3 1.0(2) . . . . ?
C15 O4 C14 C11 -178.32(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.079
_oxdiff_exptl_absorpt_empirical_full_min 0.513
