# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_ml-88_auto
_database_code_depnum_ccdc_archive 'CCDC 2487225'
loop_
_audit_author_name
_audit_author_address
Monika
;Department of Chemistry, University of Delhi
India
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-09-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        
3-(2-chloro-4-fluorophenyl)-1-methylquinoxalin-2(1H)-one
_chemical_formula_moiety         'C15 H10 Cl F N2 O'
_chemical_formula_sum            'C15 H10 Cl F N2 O'
_chemical_formula_weight         288.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.4093(3)
_cell_length_b                   7.4847(4)
_cell_length_c                   12.1426(7)
_cell_angle_alpha                89.291(4)
_cell_angle_beta                 78.306(4)
_cell_angle_gamma                87.354(4)
_cell_volume                     658.70(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3443
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0030
_cell_measurement_theta_min      2.7010
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.121a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'slow evapouration in chloroform'
_exptl_crystal_recrystallization_method 'slow evapouration in chloroform'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.805
_diffrn_reflns_theta_min         1.713
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  40.00   0.50    1.50    --   -4.88  81.00 125.00  134
  2  ω    -21.00  14.00   0.50    1.50    --   -4.88 -99.00 -30.00   70
  3  ω    -10.00  24.00   0.50    1.50    --   -4.88 -99.00-120.00   68
  4  ω    -15.00  12.00   0.50    1.50    --   -4.88 -99.00-150.00   54
  5  ω    -23.00  28.00   0.50    1.50    --   -4.88 -99.00-180.00  102
  6  ω    -24.00   2.00   0.50    1.50    --   -4.88 -81.00   2.00   52
  7  ω    -23.00  11.00   0.50    1.50    --    6.28 -99.00  60.00   68
  8  ω    -33.00  28.00   0.50    1.50    --    6.28 -81.00   2.00  122
  9  ω    -68.00  14.00   0.50    1.50    --    6.28 -19.00  90.00  164
;
_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      -0.0783936000
_diffrn_orient_matrix_UB_12      0.0268802000
_diffrn_orient_matrix_UB_13      -0.0223326000
_diffrn_orient_matrix_UB_21      0.0307083000
_diffrn_orient_matrix_UB_22      -0.0582979000
_diffrn_orient_matrix_UB_23      -0.0462860000
_diffrn_orient_matrix_UB_31      -0.0498743000
_diffrn_orient_matrix_UB_32      -0.0698475000
_diffrn_orient_matrix_UB_33      0.0302874000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name ML-88.par
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2155
_reflns_number_total             3334
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.44.121a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.107
_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)+(0.0879P)²+0.1186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1867
_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:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl00 Cl 0.49708(11) 0.58967(9) 0.80876(7) 0.0807(3) Uani 1 1 d . . . . .
N002 N 0.6289(2) 0.1847(2) 0.62150(14) 0.0458(4) Uani 1 1 d . . . . .
O003 O 0.8633(2) 0.3103(3) 0.83368(14) 0.0708(6) Uani 1 1 d . . . . .
N004 N 0.9754(2) 0.2937(2) 0.64469(15) 0.0463(4) Uani 1 1 d . . . . .
F005 F 0.0543(3) 0.2282(4) 1.07758(14) 0.1159(9) Uani 1 1 d . . . . .
C006 C 0.7733(3) 0.1905(3) 0.52922(17) 0.0435(5) Uani 1 1 d . . . . .
C007 C 0.9479(3) 0.2477(3) 0.53910(18) 0.0435(5) Uani 1 1 d . . . . .
C008 C 0.5016(3) 0.2294(3) 0.81664(17) 0.0458(5) Uani 1 1 d . . . . .
C009 C 0.6577(3) 0.2306(3) 0.71804(17) 0.0432(5) Uani 1 1 d . . . . .
C00A C 0.8389(3) 0.2824(3) 0.73915(19) 0.0486(5) Uani 1 1 d . . . . .
C00B C 0.4195(3) 0.3877(3) 0.86546(18) 0.0502(5) Uani 1 1 d . . . . .
C00C C 0.7434(3) 0.1394(3) 0.42464(19) 0.0525(6) Uani 1 1 d . . . . .
H00C H 0.628818 0.099648 0.418498 0.063 Uiso 1 1 calc R U . . .
C00D C 1.0866(3) 0.2557(3) 0.4421(2) 0.0539(6) Uani 1 1 d . . . . .
H00D H 1.202119 0.295083 0.446641 0.065 Uiso 1 1 calc R U . . .
C00E C 0.8807(4) 0.1470(4) 0.3312(2) 0.0577(6) Uani 1 1 d . . . . .
H00E H 0.859582 0.113201 0.261633 0.069 Uiso 1 1 calc R U . . .
C00F C 1.0522(4) 0.2056(4) 0.3405(2) 0.0599(6) Uani 1 1 d . . . . .
H00F H 1.145270 0.210855 0.276603 0.072 Uiso 1 1 calc R U . . .
C00G C 0.2703(4) 0.3892(4) 0.9543(2) 0.0674(7) Uani 1 1 d . . . . .
H00G H 0.217010 0.495746 0.987071 0.081 Uiso 1 1 calc R U . . .
C00H C 1.1562(3) 0.3495(4) 0.6589(2) 0.0617(7) Uani 1 1 d . . . . .
H00A H 1.245954 0.252529 0.639111 0.093 Uiso 1 1 calc R U . . .
H00B H 1.149505 0.382145 0.735929 0.093 Uiso 1 1 calc R U . . .
H00H H 1.191671 0.450367 0.611152 0.093 Uiso 1 1 calc R U . . .
C00I C 0.4287(4) 0.0703(4) 0.8586(2) 0.0636(7) Uani 1 1 d . . . . .
H00I H 0.480582 -0.037010 0.826334 0.076 Uiso 1 1 calc R U . . .
C00J C 0.2042(4) 0.2276(5) 0.9919(2) 0.0724(8) Uani 1 1 d . . . . .
C00K C 0.2788(4) 0.0679(5) 0.9483(3) 0.0796(9) Uani 1 1 d . . . . .
H00K H 0.231008 -0.039464 0.977601 0.096 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
Cl00 C00B 1.728(2) . ?
N002 C006 1.386(3) . ?
N002 C009 1.287(3) . ?
O003 C00A 1.220(3) . ?
N004 C007 1.388(3) . ?
N004 C00A 1.371(3) . ?
N004 C00H 1.465(3) . ?
F005 C00J 1.359(3) . ?
C006 C007 1.409(3) . ?
C006 C00C 1.394(3) . ?
C007 C00D 1.400(3) . ?
C008 C009 1.487(3) . ?
C008 C00B 1.389(3) . ?
C008 C00I 1.379(3) . ?
C009 C00A 1.486(3) . ?
C00B C00G 1.379(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.364(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.369(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.389(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.365(4) . ?
C00H H00A 0.9600 . ?
C00H H00B 0.9600 . ?
C00H H00H 0.9600 . ?
C00I H00I 0.9300 . ?
C00I C00K 1.390(4) . ?
C00J C00K 1.360(5) . ?
C00K H00K 0.9300 . ?

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
C009 N002 C006 118.48(17) . . ?
C007 N004 C00H 120.30(18) . . ?
C00A N004 C007 121.95(17) . . ?
C00A N004 C00H 117.71(18) . . ?
N002 C006 C007 121.46(18) . . ?
N002 C006 C00C 118.76(18) . . ?
C00C C006 C007 119.78(19) . . ?
N004 C007 C006 118.62(18) . . ?
N004 C007 C00D 122.68(19) . . ?
C00D C007 C006 118.70(19) . . ?
C00B C008 C009 121.2(2) . . ?
C00I C008 C009 120.5(2) . . ?
C00I C008 C00B 118.2(2) . . ?
N002 C009 C008 118.63(17) . . ?
N002 C009 C00A 124.48(18) . . ?
C00A C009 C008 116.88(17) . . ?
O003 C00A N004 123.15(19) . . ?
O003 C00A C009 122.1(2) . . ?
N004 C00A C009 114.79(18) . . ?
C008 C00B Cl00 119.36(17) . . ?
C00G C00B Cl00 118.5(2) . . ?
C00G C00B C008 122.0(2) . . ?
C006 C00C H00C 119.7 . . ?
C00E C00C C006 120.6(2) . . ?
C00E C00C H00C 119.7 . . ?
C007 C00D H00D 120.0 . . ?
C00F C00D C007 120.0(2) . . ?
C00F C00D H00D 120.0 . . ?
C00C C00E H00E 120.2 . . ?
C00C C00E C00F 119.7(2) . . ?
C00F C00E H00E 120.2 . . ?
C00D C00F C00E 121.2(2) . . ?
C00D C00F H00F 119.4 . . ?
C00E C00F H00F 119.4 . . ?
C00B C00G H00G 121.5 . . ?
C00J C00G C00B 117.1(3) . . ?
C00J C00G H00G 121.5 . . ?
N004 C00H H00A 109.5 . . ?
N004 C00H H00B 109.5 . . ?
N004 C00H H00H 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00H 109.5 . . ?
H00B C00H H00H 109.5 . . ?
C008 C00I H00I 119.5 . . ?
C008 C00I C00K 121.0(3) . . ?
C00K C00I H00I 119.5 . . ?
F005 C00J C00G 117.4(3) . . ?
F005 C00J C00K 118.7(3) . . ?
C00K C00J C00G 123.9(2) . . ?
C00I C00K H00K 121.1 . . ?
C00J C00K C00I 117.8(3) . . ?
C00J C00K H00K 121.1 . . ?

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
Cl00 C00B C00G C00J 175.46(19) . . . . ?
N002 C006 C007 N004 1.9(3) . . . . ?
N002 C006 C007 C00D -178.1(2) . . . . ?
N002 C006 C00C C00E 178.5(2) . . . . ?
N002 C009 C00A O003 -173.7(2) . . . . ?
N002 C009 C00A N004 5.5(3) . . . . ?
N004 C007 C00D C00F 178.9(2) . . . . ?
F005 C00J C00K C00I 178.2(2) . . . . ?
C006 N002 C009 C008 178.30(19) . . . . ?
C006 N002 C009 C00A -2.9(3) . . . . ?
C006 C007 C00D C00F -1.1(3) . . . . ?
C006 C00C C00E C00F 0.3(4) . . . . ?
C007 N004 C00A O003 174.8(2) . . . . ?
C007 N004 C00A C009 -4.3(3) . . . . ?
C007 C006 C00C C00E -1.2(4) . . . . ?
C007 C00D C00F C00E 0.3(4) . . . . ?
C008 C009 C00A O003 5.2(3) . . . . ?
C008 C009 C00A N004 -175.68(19) . . . . ?
C008 C00B C00G C00J -0.8(4) . . . . ?
C008 C00I C00K C00J 1.3(4) . . . . ?
C009 N002 C006 C007 -0.9(3) . . . . ?
C009 N002 C006 C00C 179.4(2) . . . . ?
C009 C008 C00B Cl00 1.3(3) . . . . ?
C009 C008 C00B C00G 177.6(2) . . . . ?
C009 C008 C00I C00K -177.8(2) . . . . ?
C00A N004 C007 C006 1.0(3) . . . . ?
C00A N004 C007 C00D -179.0(2) . . . . ?
C00B C008 C009 N002 -108.7(2) . . . . ?
C00B C008 C009 C00A 72.4(3) . . . . ?
C00B C008 C00I C00K -0.9(4) . . . . ?
C00B C00G C00J F005 -178.4(2) . . . . ?
C00B C00G C00J C00K 1.2(4) . . . . ?
C00C C006 C007 N004 -178.4(2) . . . . ?
C00C C006 C007 C00D 1.6(3) . . . . ?
C00C C00E C00F C00D 0.1(4) . . . . ?
C00G C00J C00K C00I -1.4(5) . . . . ?
C00H N004 C007 C006 178.5(2) . . . . ?
C00H N004 C007 C00D -1.5(3) . . . . ?
C00H N004 C00A O003 -2.7(4) . . . . ?
C00H N004 C00A C009 178.16(19) . . . . ?
C00I C008 C009 N002 68.1(3) . . . . ?
C00I C008 C009 C00A -110.9(2) . . . . ?
C00I C008 C00B Cl00 -175.53(17) . . . . ?
C00I C008 C00B C00G 0.7(3) . . . . ?

_olex2_submission_original_sample_id 'ML 88'
_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 1.487
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_ml-95_auto
_database_code_depnum_ccdc_archive 'CCDC 2487347'
loop_
_audit_author_name
_audit_author_address
Monika
;Department of Chemistry, University of Delhi
India
;
_audit_update_record             
;
2025-09-11 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-09-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        
3-(2-bromophenyl)-6,7-dichloro-1-methylquinoxalin-2(1H)-one
_chemical_formula_moiety         'C15 H9 Br Cl2 N2 O'
_chemical_formula_sum            'C15 H9 Br Cl2 N2 O'
_chemical_formula_weight         384.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I 1 a 1'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   6.8975(7)
_cell_length_b                   31.1454(18)
_cell_length_c                   7.4421(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.773(11)
_cell_angle_gamma                90
_cell_volume                     1484.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4987
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1910
_cell_measurement_theta_min      2.9980
_shelx_estimated_absorpt_T_max   0.745
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    3.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.121a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_preparation       'slow evapouration in chloroform'
_exptl_crystal_recrystallization_method 'slow evapouration in chloroform'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1559
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32431
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.076
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      293(2)
_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 0.913
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  78.00   0.50    0.05    --    5.81  57.00 120.00  174
  2  ω    -67.00  19.00   0.50    0.05    --    5.81 -38.00  60.00  172
  3  ω    -67.00  19.00   0.50    0.05    --    5.81 -38.00  30.00  172
  4  ω    -68.00  19.00   0.50    0.05    --    5.81 -19.00  90.00  174
  5  ω    -68.00  19.00   0.50    0.05    --    5.81 -19.00 150.00  174
  6  ω    -68.00  20.00   0.50    0.05    --    5.81 -33.00 -88.51  176
  7  ω    -68.00  19.00   0.50    0.05    --    5.81 -19.00-150.00  174
  8  ω    -67.00  15.00   0.50    0.05    --    5.81 -38.00-180.00  164
  9  ω     -7.00  81.00   0.50    0.05    --    5.81  19.00-120.00  176
 10  ω    -17.00  71.00   0.50    0.05    --   -4.41  19.00 -30.00  176
 11  ω    -40.00   7.00   0.50    0.05    --   -4.41 103.00  54.00   94
 12  ω    -23.00  39.00   0.50    0.05    --    5.81 -99.00 150.00  124
 13  ω    -23.00  29.00   0.50    0.05    --   -4.41 -99.00   0.00  104
 14  ω     -7.00  41.00   0.50    0.05    --    5.81-103.00 -47.00   96
 15  ω    -23.00  29.00   0.50    0.05    --   -4.41 -99.00-120.00  104
 16  ω    -17.00  71.00   0.50    0.05    --   -4.41  19.00  60.00  176
;
_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      0.0134953000
_diffrn_orient_matrix_UB_12      -0.0217804000
_diffrn_orient_matrix_UB_13      -0.0205781000
_diffrn_orient_matrix_UB_21      -0.1088169000
_diffrn_orient_matrix_UB_22      -0.0017984000
_diffrn_orient_matrix_UB_23      -0.0533323000
_diffrn_orient_matrix_UB_31      0.0154535000
_diffrn_orient_matrix_UB_32      0.0063800000
_diffrn_orient_matrix_UB_33      -0.0851953000
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_oxdiff_measurement_exp_name ML-95.par
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                2293
_reflns_number_total             4106
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.44.121a (Rigaku OD, 2025)'
_computing_data_collection       'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_data_reduction        'CrysAlisPro 1.171.44.121a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 841 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.104(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4106
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1185
_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:
 C00B(H00B), C00D(H00D), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00I(H00A,H00C,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.15413(14) 0.68892(3) 0.55122(13) 0.0680(3) Uani 1 1 d . . . . .
Cl00 Cl 0.5011(3) 0.42561(5) 0.5088(3) 0.0587(5) Uani 1 1 d . . . . .
Cl1 Cl 0.3669(3) 0.44476(6) 0.0616(3) 0.0640(6) Uani 1 1 d . . . . .
O004 O 0.4624(13) 0.67480(18) 0.3001(8) 0.077(2) Uani 1 1 d . . . . .
N005 N 0.5379(9) 0.58705(16) 0.6203(8) 0.0370(12) Uani 1 1 d . . . . .
N006 N 0.4215(9) 0.60424(16) 0.2236(8) 0.0381(13) Uani 1 1 d . . . . .
C007 C 0.4396(11) 0.5620(2) 0.2873(10) 0.0347(14) Uani 1 1 d . . . . .
C008 C 0.5224(10) 0.62561(19) 0.5588(9) 0.0353(15) Uani 1 1 d . . . . .
C009 C 0.5797(12) 0.6612(2) 0.7035(10) 0.0416(16) Uani 1 1 d . . . . .
C00A C 0.4957(10) 0.55363(19) 0.4849(9) 0.0342(14) Uani 1 1 d . . . . .
C00B C 0.5115(10) 0.5119(2) 0.5510(10) 0.0386(15) Uani 1 1 d . . . . .
H00B H 0.546845 0.506510 0.682272 0.046 Uiso 1 1 calc R U . . .
C00C C 0.4181(11) 0.4860(2) 0.2252(11) 0.0442(17) Uani 1 1 d . . . . .
C00D C 0.4006(11) 0.5276(2) 0.1582(10) 0.0423(16) Uani 1 1 d . . . . .
H00D H 0.362736 0.532816 0.026566 0.051 Uiso 1 1 calc R U . . .
C00E C 0.4750(10) 0.47777(19) 0.4222(10) 0.0399(16) Uani 1 1 d . . . . .
C00F C 0.4657(13) 0.6382(2) 0.3526(10) 0.0471(18) Uani 1 1 d . . . . .
C00G C 0.4396(13) 0.6920(2) 0.7172(11) 0.0469(18) Uani 1 1 d . . . . .
C00H C 0.7828(14) 0.6637(3) 0.8337(11) 0.054(2) Uani 1 1 d . . . . .
H00H H 0.878957 0.643280 0.828346 0.065 Uiso 1 1 calc R U . . .
C00I C 0.3638(14) 0.6147(3) 0.0181(10) 0.056(2) Uani 1 1 d . . . . .
H00A H 0.471448 0.604941 -0.024902 0.084 Uiso 1 1 calc R U . . .
H00C H 0.347482 0.645174 0.000578 0.084 Uiso 1 1 calc R U . . .
H00E H 0.234691 0.600706 -0.055960 0.084 Uiso 1 1 calc R U . . .
C00J C 0.7034(18) 0.7258(3) 0.9794(13) 0.073(3) Uani 1 1 d . . . . .
H00J H 0.745355 0.747534 1.071664 0.087 Uiso 1 1 calc R U . . .
C00K C 0.5024(17) 0.7242(2) 0.8545(12) 0.061(2) Uani 1 1 d . . . . .
H00K H 0.407133 0.744713 0.861001 0.073 Uiso 1 1 calc R U . . .
C00L C 0.8472(16) 0.6957(3) 0.9719(12) 0.068(2) Uani 1 1 d . . . . .
H00L H 0.984969 0.696878 1.058428 0.081 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00G 1.899(9) . ?
Cl00 C00E 1.732(6) . ?
Cl1 C00C 1.715(7) . ?
O004 C00F 1.202(8) . ?
N005 C008 1.275(8) . ?
N005 C00A 1.402(8) . ?
N006 C007 1.389(8) . ?
N006 C00F 1.384(8) . ?
N006 C00I 1.467(9) . ?
C007 C00A 1.400(9) . ?
C007 C00D 1.396(9) . ?
C008 C009 1.493(9) . ?
C008 C00F 1.489(9) . ?
C009 C00G 1.391(10) . ?
C009 C00H 1.378(11) . ?
C00A C00B 1.381(9) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.389(9) . ?
C00C C00D 1.377(10) . ?
C00C C00E 1.394(10) . ?
C00D H00D 0.9300 . ?
C00G C00K 1.383(10) . ?
C00H H00H 0.9300 . ?
C00H C00L 1.382(11) . ?
C00I H00A 0.9600 . ?
C00I H00C 0.9600 . ?
C00I H00E 0.9600 . ?
C00J H00J 0.9300 . ?
C00J C00K 1.354(13) . ?
C00J C00L 1.382(14) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?

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
C008 N005 C00A 118.3(6) . . ?
C007 N006 C00I 121.4(5) . . ?
C00F N006 C007 121.3(5) . . ?
C00F N006 C00I 117.3(6) . . ?
N006 C007 C00A 119.3(6) . . ?
N006 C007 C00D 121.5(6) . . ?
C00D C007 C00A 119.3(6) . . ?
N005 C008 C009 118.4(6) . . ?
N005 C008 C00F 124.9(6) . . ?
C00F C008 C009 116.5(5) . . ?
C00G C009 C008 124.0(7) . . ?
C00H C009 C008 118.5(6) . . ?
C00H C009 C00G 117.6(7) . . ?
C007 C00A N005 121.3(6) . . ?
C00B C00A N005 118.4(6) . . ?
C00B C00A C007 120.2(6) . . ?
C00A C00B H00B 119.9 . . ?
C00A C00B C00E 120.3(6) . . ?
C00E C00B H00B 119.9 . . ?
C00D C00C Cl1 118.7(6) . . ?
C00D C00C C00E 120.5(6) . . ?
C00E C00C Cl1 120.8(5) . . ?
C007 C00D H00D 119.9 . . ?
C00C C00D C007 120.2(6) . . ?
C00C C00D H00D 119.9 . . ?
C00B C00E Cl00 119.5(5) . . ?
C00B C00E C00C 119.5(6) . . ?
C00C C00E Cl00 120.9(5) . . ?
O004 C00F N006 121.8(6) . . ?
O004 C00F C008 123.4(6) . . ?
N006 C00F C008 114.8(5) . . ?
C009 C00G Br01 119.9(5) . . ?
C00K C00G Br01 118.8(7) . . ?
C00K C00G C009 121.2(8) . . ?
C009 C00H H00H 119.1 . . ?
C009 C00H C00L 121.7(8) . . ?
C00L C00H H00H 119.1 . . ?
N006 C00I H00A 109.5 . . ?
N006 C00I H00C 109.5 . . ?
N006 C00I H00E 109.5 . . ?
H00A C00I H00C 109.5 . . ?
H00A C00I H00E 109.5 . . ?
H00C C00I H00E 109.5 . . ?
C00K C00J H00J 119.5 . . ?
C00K C00J C00L 121.0(8) . . ?
C00L C00J H00J 119.5 . . ?
C00G C00K H00K 120.2 . . ?
C00J C00K C00G 119.6(8) . . ?
C00J C00K H00K 120.2 . . ?
C00H C00L C00J 118.9(9) . . ?
C00H C00L H00L 120.6 . . ?
C00J C00L H00L 120.6 . . ?

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
Br01 C00G C00K C00J 177.2(6) . . . . ?
Cl1 C00C C00D C007 179.5(5) . . . . ?
Cl1 C00C C00E Cl00 1.4(8) . . . . ?
Cl1 C00C C00E C00B -178.7(5) . . . . ?
N005 C008 C009 C00G -116.4(7) . . . . ?
N005 C008 C009 C00H 62.7(9) . . . . ?
N005 C008 C00F O004 -176.2(8) . . . . ?
N005 C008 C00F N006 2.2(11) . . . . ?
N005 C00A C00B C00E -178.7(6) . . . . ?
N006 C007 C00A N005 -1.3(9) . . . . ?
N006 C007 C00A C00B 179.0(6) . . . . ?
N006 C007 C00D C00C -179.5(6) . . . . ?
C007 N006 C00F O004 175.6(7) . . . . ?
C007 N006 C00F C008 -2.9(10) . . . . ?
C007 C00A C00B C00E 0.9(10) . . . . ?
C008 N005 C00A C007 0.6(9) . . . . ?
C008 N005 C00A C00B -179.8(6) . . . . ?
C008 C009 C00G Br01 2.2(9) . . . . ?
C008 C009 C00G C00K -180.0(6) . . . . ?
C008 C009 C00H C00L -179.9(7) . . . . ?
C009 C008 C00F O004 -0.8(12) . . . . ?
C009 C008 C00F N006 177.6(6) . . . . ?
C009 C00G C00K C00J -0.6(11) . . . . ?
C009 C00H C00L C00J 0.2(13) . . . . ?
C00A N005 C008 C009 -176.4(6) . . . . ?
C00A N005 C008 C00F -1.1(10) . . . . ?
C00A C007 C00D C00C -0.3(10) . . . . ?
C00A C00B C00E Cl00 178.6(5) . . . . ?
C00A C00B C00E C00C -1.2(10) . . . . ?
C00D C007 C00A N005 179.5(6) . . . . ?
C00D C007 C00A C00B -0.2(10) . . . . ?
C00D C00C C00E Cl00 -179.1(6) . . . . ?
C00D C00C C00E C00B 0.8(10) . . . . ?
C00E C00C C00D C007 0.0(11) . . . . ?
C00F N006 C007 C00A 2.5(10) . . . . ?
C00F N006 C007 C00D -178.2(7) . . . . ?
C00F C008 C009 C00G 67.9(9) . . . . ?
C00F C008 C009 C00H -113.0(8) . . . . ?
C00G C009 C00H C00L -0.7(11) . . . . ?
C00H C009 C00G Br01 -176.9(5) . . . . ?
C00H C009 C00G C00K 0.9(10) . . . . ?
C00I N006 C007 C00A 179.8(7) . . . . ?
C00I N006 C007 C00D -1.0(10) . . . . ?
C00I N006 C00F O004 -1.8(12) . . . . ?
C00I N006 C00F C008 179.8(7) . . . . ?
C00K C00J C00L C00H 0.2(13) . . . . ?
C00L C00J C00K C00G 0.0(13) . . . . ?

_olex2_submission_original_sample_id 'ML 95'
_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 1.638
_oxdiff_exptl_absorpt_empirical_full_min 0.592
