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

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

data_3J
_database_code_depnum_ccdc_archive 'CCDC 2253523'
loop_
_audit_author_name
_audit_author_address
'Arunava Sengupta'
;Indian Institute of Technology (ISM) Dhanbad
India
;
_audit_update_record             
;
2023-04-03 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Isatin
_chemical_name_systematic        3J
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_absolute_configuration .
_chemical_melting_point          413.0
_chemical_oxdiff_formula         'C68 H52 O8 N1 '
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.5072(8)
_cell_length_b                   23.008(3)
_cell_length_c                   7.4733(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1290.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1217
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0680
_cell_measurement_theta_min      3.5370
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.512
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'orange red'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.991
_exptl_transmission_factor_min   0.975
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3374
_diffrn_reflns_point_group_measured_fraction_full 0.768
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_theta_full        25.019
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  42.00   1.00   32.50    --   13.76  77.00  90.00   52
  2  ω    -82.00 -19.00   1.00   32.50    --  -15.95 -57.00   0.00   63
  3  ω    -29.00  -3.00   1.00   32.50    --  -15.95 -57.00 -90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0513890000
_diffrn_orient_matrix_UB_12      0.0207508000
_diffrn_orient_matrix_UB_13      0.0249770000
_diffrn_orient_matrix_UB_21      -0.0791611000
_diffrn_orient_matrix_UB_22      -0.0137151000
_diffrn_orient_matrix_UB_23      -0.0161792000
_diffrn_orient_matrix_UB_31      0.0002802000
_diffrn_orient_matrix_UB_32      -0.0916717000
_diffrn_orient_matrix_UB_33      0.0080851000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.420
_reflns_Friedel_fraction_full    0.496
_reflns_Friedel_fraction_max     0.495
_reflns_number_gt                1259
_reflns_number_total             1746
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   .
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      0.975
_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)+(0.0308P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0731
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C16(H16), C12(H12), C13(H13), C5(H5), C15(H15), C14(H14)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.3435(4) 0.21669(11) 0.2073(3) 0.0758(8) Uani 1 1 d . . . . .
O1 O 0.3011(3) 0.34326(10) 0.1728(3) 0.0782(8) Uani 1 1 d . . . . .
N1 N 0.4402(3) 0.34229(11) 0.4480(3) 0.0503(7) Uani 1 1 d . . . . .
C8 C 0.5045(4) 0.29851(13) 0.5676(4) 0.0428(8) Uani 1 1 d . . . . .
C9 C 0.4750(4) 0.24367(13) 0.4917(4) 0.0446(8) Uani 1 1 d . . . . .
C11 C 0.5895(4) 0.43902(13) 0.4331(4) 0.0459(8) Uani 1 1 d . . . . .
C7 C 0.5845(4) 0.30390(15) 0.7346(4) 0.0484(8) Uani 1 1 d . . . . .
C4 C 0.5194(4) 0.19240(14) 0.5805(5) 0.0543(9) Uani 1 1 d . . . . .
H4 H 0.499271 0.156236 0.528778 0.065 Uiso 1 1 calc R U . . .
C3 C 0.3924(4) 0.25141(15) 0.3184(4) 0.0528(9) Uani 1 1 d . . . . .
C1 C 0.4248(4) 0.40462(13) 0.4796(4) 0.0579(9) Uani 1 1 d . . . . .
H1A H 0.397044 0.410899 0.604855 0.069 Uiso 1 1 calc R U . . .
H1B H 0.325752 0.419439 0.409768 0.069 Uiso 1 1 calc R U . . .
C6 C 0.6264(4) 0.25157(17) 0.8202(4) 0.0564(9) Uani 1 1 d . . . . .
H6 H 0.679114 0.253440 0.932604 0.068 Uiso 1 1 calc R U . . .
C2 C 0.3698(5) 0.31821(16) 0.2970(5) 0.0566(9) Uani 1 1 d . . . . .
C16 C 0.7218(5) 0.41696(13) 0.3260(4) 0.0568(9) Uani 1 1 d . . . . .
H16 H 0.711992 0.379118 0.283333 0.068 Uiso 1 1 calc R U . . .
C12 C 0.6077(5) 0.49571(14) 0.4948(5) 0.0626(10) Uani 1 1 d . . . . .
H12 H 0.519877 0.511550 0.567788 0.075 Uiso 1 1 calc R U . . .
C13 C 0.7530(6) 0.52857(16) 0.4496(6) 0.0748(12) Uani 1 1 d . . . . .
H13 H 0.762760 0.566436 0.491940 0.090 Uiso 1 1 calc R U . . .
C5 C 0.5943(4) 0.19749(17) 0.7483(4) 0.0599(10) Uani 1 1 d . . . . .
H5 H 0.623324 0.164294 0.813093 0.072 Uiso 1 1 calc R U . . .
C10 C 0.6301(5) 0.36022(15) 0.8266(5) 0.0703(11) Uani 1 1 d . . . . .
H10A H 0.682204 0.386523 0.741744 0.105 Uiso 1 1 calc R U . . .
H10B H 0.713447 0.352869 0.921419 0.105 Uiso 1 1 calc R U . . .
H10C H 0.523803 0.377154 0.875356 0.105 Uiso 1 1 calc R U . . .
C15 C 0.8693(5) 0.44973(17) 0.2801(5) 0.0735(12) Uani 1 1 d . . . . .
H15 H 0.957912 0.433968 0.207848 0.088 Uiso 1 1 calc R U . . .
C14 C 0.8841(6) 0.50603(18) 0.3423(6) 0.0800(12) Uani 1 1 d . . . . .
H14 H 0.982401 0.528537 0.311608 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
O2 C3 1.209(4) . ?
O1 C2 1.208(4) . ?
N1 C8 1.431(4) . ?
N1 C1 1.458(3) . ?
N1 C2 1.364(4) . ?
C8 C9 1.401(4) . ?
C8 C7 1.391(4) . ?
C9 C4 1.394(4) . ?
C9 C3 1.447(4) . ?
C11 C1 1.509(4) . ?
C11 C16 1.373(4) . ?
C11 C12 1.390(4) . ?
C7 C6 1.399(4) . ?
C7 C10 1.506(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C3 C2 1.555(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C5 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.383(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.369(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.372(5) . ?
C5 H5 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.381(5) . ?
C14 H14 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
C8 N1 C1 128.2(3) . . ?
C2 N1 C8 111.2(3) . . ?
C2 N1 C1 120.2(3) . . ?
C9 C8 N1 109.1(3) . . ?
C7 C8 N1 130.1(3) . . ?
C7 C8 C9 120.8(3) . . ?
C8 C9 C3 108.6(3) . . ?
C4 C9 C8 122.1(3) . . ?
C4 C9 C3 129.3(3) . . ?
C16 C11 C1 122.2(3) . . ?
C16 C11 C12 118.0(3) . . ?
C12 C11 C1 119.8(3) . . ?
C8 C7 C6 115.5(3) . . ?
C8 C7 C10 125.8(3) . . ?
C6 C7 C10 118.7(3) . . ?
C9 C4 H4 121.4 . . ?
C5 C4 C9 117.3(3) . . ?
C5 C4 H4 121.4 . . ?
O2 C3 C9 131.6(3) . . ?
O2 C3 C2 123.3(3) . . ?
C9 C3 C2 105.1(3) . . ?
N1 C1 C11 114.4(3) . . ?
N1 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C11 C1 H1A 108.7 . . ?
C11 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C7 C6 H6 117.9 . . ?
C5 C6 C7 124.1(3) . . ?
C5 C6 H6 117.9 . . ?
O1 C2 N1 127.4(3) . . ?
O1 C2 C3 126.7(3) . . ?
N1 C2 C3 105.9(3) . . ?
C11 C16 H16 119.3 . . ?
C11 C16 C15 121.5(3) . . ?
C15 C16 H16 119.3 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.8 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?

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
O2 C3 C2 O1 1.0(6) . . . . ?
O2 C3 C2 N1 180.0(3) . . . . ?
N1 C8 C9 C4 -178.1(3) . . . . ?
N1 C8 C9 C3 0.8(3) . . . . ?
N1 C8 C7 C6 177.8(3) . . . . ?
N1 C8 C7 C10 -3.0(5) . . . . ?
C8 N1 C1 C11 88.5(3) . . . . ?
C8 N1 C2 O1 178.1(3) . . . . ?
C8 N1 C2 C3 -0.8(3) . . . . ?
C8 C9 C4 C5 0.1(4) . . . . ?
C8 C9 C3 O2 -179.8(4) . . . . ?
C8 C9 C3 C2 -1.3(3) . . . . ?
C8 C7 C6 C5 0.5(5) . . . . ?
C9 C8 C7 C6 -1.9(4) . . . . ?
C9 C8 C7 C10 177.3(3) . . . . ?
C9 C4 C5 C6 -1.5(5) . . . . ?
C9 C3 C2 O1 -177.7(3) . . . . ?
C9 C3 C2 N1 1.3(3) . . . . ?
C11 C16 C15 C14 -0.3(5) . . . . ?
C11 C12 C13 C14 -0.1(6) . . . . ?
C7 C8 C9 C4 1.7(4) . . . . ?
C7 C8 C9 C3 -179.4(3) . . . . ?
C7 C6 C5 C4 1.2(5) . . . . ?
C4 C9 C3 O2 -1.0(6) . . . . ?
C4 C9 C3 C2 177.5(3) . . . . ?
C3 C9 C4 C5 -178.6(3) . . . . ?
C1 N1 C8 C9 172.4(3) . . . . ?
C1 N1 C8 C7 -7.3(5) . . . . ?
C1 N1 C2 O1 5.1(5) . . . . ?
C1 N1 C2 C3 -173.9(3) . . . . ?
C1 C11 C16 C15 177.9(3) . . . . ?
C1 C11 C12 C13 -177.8(3) . . . . ?
C2 N1 C8 C9 0.0(3) . . . . ?
C2 N1 C8 C7 -179.7(3) . . . . ?
C2 N1 C1 C11 -99.7(3) . . . . ?
C16 C11 C1 N1 17.1(4) . . . . ?
C16 C11 C12 C13 0.2(5) . . . . ?
C16 C15 C14 C13 0.4(6) . . . . ?
C12 C11 C1 N1 -165.0(3) . . . . ?
C12 C11 C16 C15 0.0(5) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C10 C7 C6 C5 -178.8(3) . . . . ?

_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.705
####################################################################### 
# 
# 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_2K
_database_code_depnum_ccdc_archive 'CCDC 2253525'
loop_
_audit_author_name
_audit_author_address
'Arunava Sengupta'
;Indian Institute of Technology (ISM) Dhanbad
India
;
_audit_update_record             
;
2023-05-11 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            3-acetoxy-indole
_chemical_name_systematic        2K
_chemical_formula_moiety         'C17 H14 Br N O2'
_chemical_formula_sum            'C17 H14 Br N O2'
_chemical_formula_weight         344.20
_chemical_melting_point          448.0
_chemical_oxdiff_formula         'C68 H56 Br4 N8 O4 '
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'
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           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                   9.6226(8)
_cell_length_b                   17.3895(10)
_cell_length_c                   9.3029(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.767(9)
_cell_angle_gamma                90
_cell_volume                     1490.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2713
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7950
_cell_measurement_theta_min      2.9130
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.372
_exptl_absorpt_coefficient_mu    2.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   0.680
_exptl_transmission_factor_min   0.613
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.407
_diffrn_reflns_theta_min         2.210
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0303
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  29.00   1.00   37.50    --   13.76 -57.00 -30.00   39
  2  ω    -78.00   6.00   1.00   37.50    --  -15.95   0.00-120.00   84
  3  ω     11.00  53.00   1.00   37.50    --  -15.95   0.00-120.00   42
  4  ω    -40.00   7.00   1.00   37.50    --  -15.95 -77.00  60.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011594000
_diffrn_orient_matrix_UB_12      0.0378162000
_diffrn_orient_matrix_UB_13      -0.0282707000
_diffrn_orient_matrix_UB_21      0.0668275000
_diffrn_orient_matrix_UB_22      0.0071047000
_diffrn_orient_matrix_UB_23      0.0553592000
_diffrn_orient_matrix_UB_31      0.0381729000
_diffrn_orient_matrix_UB_32      -0.0135538000
_diffrn_orient_matrix_UB_33      -0.0497681000
_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              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2543
_reflns_number_total             3479
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.117
_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)+(0.0413P)²+0.4537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C2(H2), C15(H15), C6(H6), C11(H11), C13(H13), C14(H14),
 C12(H12)
1.c Idealised Me refined as rotating group:
 C00I(H00A,H00B,H00C)
;
_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
Br1 Br 0.74221(4) 0.23499(2) 0.32957(4) 0.06637(15) Uani 1 1 d . . . . .
O1 O 0.6346(2) 0.52294(12) 0.63287(19) 0.0506(5) Uani 1 1 d . . . . .
N1 N 0.8414(2) 0.57485(14) 0.3861(2) 0.0467(6) Uani 1 1 d . . . . .
O2 O 0.8069(2) 0.45511(15) 0.7953(2) 0.0712(7) Uani 1 1 d . . . . .
C9 C 0.7495(3) 0.46421(16) 0.4483(3) 0.0407(6) Uani 1 1 d . . . . .
C8 C 0.8276(3) 0.49788(17) 0.3560(3) 0.0421(6) Uani 1 1 d . . . . .
C4 C 0.7217(3) 0.38558(17) 0.4402(3) 0.0448(6) Uani 1 1 d . . . . .
H4 H 0.671269 0.362439 0.500139 0.054 Uiso 1 1 calc R U . . .
C10 C 0.8181(3) 0.64874(15) 0.1533(3) 0.0425(6) Uani 1 1 d . . . . .
C3 C 0.7186(3) 0.52650(17) 0.5329(3) 0.0437(6) Uani 1 1 d . . . . .
C00A C 0.6906(3) 0.48362(16) 0.7622(3) 0.0460(6) Uani 1 1 d . . . . .
C5 C 0.7715(3) 0.34332(18) 0.3403(3) 0.0472(7) Uani 1 1 d . . . . .
C7 C 0.8757(3) 0.45345(19) 0.2551(3) 0.0496(7) Uani 1 1 d . . . . .
H7 H 0.926131 0.475605 0.194140 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7730(3) 0.59181(18) 0.4929(3) 0.0487(7) Uani 1 1 d . . . . .
H2 H 0.765497 0.640480 0.531416 0.058 Uiso 1 1 calc R U . . .
C15 C 0.6740(3) 0.66872(17) 0.1245(3) 0.0502(7) Uani 1 1 d . . . . .
H15 H 0.632595 0.670548 0.203224 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8466(3) 0.37654(19) 0.2483(3) 0.0534(7) Uani 1 1 d . . . . .
H6 H 0.877272 0.345842 0.181468 0.064 Uiso 1 1 calc R U . . .
C1 C 0.9103(3) 0.63027(18) 0.3110(3) 0.0508(7) Uani 1 1 d . . . . .
H1A H 1.002834 0.609815 0.306746 0.061 Uiso 1 1 calc R U . . .
H1B H 0.929209 0.677320 0.369401 0.061 Uiso 1 1 calc R U . . .
C11 C 0.8776(3) 0.64608(19) 0.0344(3) 0.0536(7) Uani 1 1 d . . . . .
H11 H 0.974453 0.632491 0.051268 0.064 Uiso 1 1 calc R U . . .
C00I C 0.5872(3) 0.4827(2) 0.8539(3) 0.0595(8) Uani 1 1 d . . . . .
H00A H 0.590790 0.531165 0.904073 0.089 Uiso 1 1 calc R U . . .
H00B H 0.613379 0.442236 0.927053 0.089 Uiso 1 1 calc R U . . .
H00C H 0.490716 0.473923 0.789801 0.089 Uiso 1 1 calc R U . . .
C13 C 0.6511(4) 0.68333(19) -0.1352(3) 0.0623(8) Uani 1 1 d . . . . .
H13 H 0.595236 0.695005 -0.232244 0.075 Uiso 1 1 calc R U . . .
C14 C 0.5906(3) 0.68596(19) -0.0184(3) 0.0591(8) Uani 1 1 d . . . . .
H14 H 0.493536 0.699360 -0.035990 0.071 Uiso 1 1 calc R U . . .
C12 C 0.7937(4) 0.6635(2) -0.1084(3) 0.0619(9) Uani 1 1 d . . . . .
H12 H 0.834506 0.661776 -0.187618 0.074 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 C5 1.903(3) . ?
O1 C3 1.398(3) . ?
O1 C00A 1.354(3) . ?
N1 C8 1.366(4) . ?
N1 C2 1.373(3) . ?
N1 C1 1.457(3) . ?
O2 C00A 1.180(3) . ?
C9 C8 1.421(3) . ?
C9 C4 1.391(4) . ?
C9 C3 1.420(4) . ?
C8 C7 1.393(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(4) . ?
C10 C15 1.378(4) . ?
C10 C1 1.514(4) . ?
C10 C11 1.385(4) . ?
C3 C2 1.347(4) . ?
C00A C00I 1.485(4) . ?
C5 C6 1.395(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.364(4) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.373(4) . ?
C6 H6 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C12 1.375(4) . ?
C00I H00A 0.9600 . ?
C00I H00B 0.9600 . ?
C00I H00C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.374(4) . ?
C13 C12 1.366(5) . ?
C14 H14 0.9300 . ?
C12 H12 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
C00A O1 C3 117.1(2) . . ?
C8 N1 C2 108.7(2) . . ?
C8 N1 C1 125.5(2) . . ?
C2 N1 C1 125.8(3) . . ?
C4 C9 C8 119.9(2) . . ?
C4 C9 C3 135.4(2) . . ?
C3 C9 C8 104.7(2) . . ?
N1 C8 C9 108.5(2) . . ?
N1 C8 C7 130.5(2) . . ?
C7 C8 C9 121.0(3) . . ?
C9 C4 H4 121.2 . . ?
C5 C4 C9 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
C15 C10 C1 121.1(2) . . ?
C15 C10 C11 118.5(3) . . ?
C11 C10 C1 120.3(3) . . ?
O1 C3 C9 126.1(3) . . ?
C2 C3 O1 124.5(3) . . ?
C2 C3 C9 109.2(2) . . ?
O1 C00A C00I 110.8(2) . . ?
O2 C00A O1 123.2(2) . . ?
O2 C00A C00I 125.9(3) . . ?
C4 C5 Br1 119.3(2) . . ?
C4 C5 C6 122.4(3) . . ?
C6 C5 Br1 118.2(2) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 C8 118.1(3) . . ?
C6 C7 H7 120.9 . . ?
N1 C2 H2 125.5 . . ?
C3 C2 N1 108.9(3) . . ?
C3 C2 H2 125.5 . . ?
C10 C15 H15 119.4 . . ?
C14 C15 C10 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
N1 C1 C10 112.6(2) . . ?
N1 C1 H1A 109.1 . . ?
N1 C1 H1B 109.1 . . ?
C10 C1 H1A 109.1 . . ?
C10 C1 H1B 109.1 . . ?
H1A C1 H1B 107.8 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C00A C00I H00A 109.5 . . ?
C00A C00I H00B 109.5 . . ?
C00A C00I H00C 109.5 . . ?
H00A C00I H00B 109.5 . . ?
H00A C00I H00C 109.5 . . ?
H00B C00I H00C 109.5 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(3) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?

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
Br1 C5 C6 C7 -177.5(2) . . . . ?
O1 C3 C2 N1 -176.1(2) . . . . ?
N1 C8 C7 C6 179.9(3) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C9 C4 C5 Br1 177.85(19) . . . . ?
C9 C4 C5 C6 -0.4(4) . . . . ?
C9 C3 C2 N1 -1.0(3) . . . . ?
C8 N1 C2 C3 1.2(3) . . . . ?
C8 N1 C1 C10 73.9(4) . . . . ?
C8 C9 C4 C5 -0.4(4) . . . . ?
C8 C9 C3 O1 175.4(2) . . . . ?
C8 C9 C3 C2 0.4(3) . . . . ?
C8 C7 C6 C5 -0.3(4) . . . . ?
C4 C9 C8 N1 -179.5(2) . . . . ?
C4 C9 C8 C7 0.9(4) . . . . ?
C4 C9 C3 O1 -4.9(5) . . . . ?
C4 C9 C3 C2 -179.9(3) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C10 C15 C14 C13 0.0(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C3 O1 C00A O2 2.6(4) . . . . ?
C3 O1 C00A C00I -178.0(2) . . . . ?
C3 C9 C8 N1 0.3(3) . . . . ?
C3 C9 C8 C7 -179.4(2) . . . . ?
C3 C9 C4 C5 180.0(3) . . . . ?
C00A O1 C3 C9 69.3(3) . . . . ?
C00A O1 C3 C2 -116.4(3) . . . . ?
C2 N1 C8 C9 -0.9(3) . . . . ?
C2 N1 C8 C7 178.8(3) . . . . ?
C2 N1 C1 C10 -102.5(3) . . . . ?
C15 C10 C1 N1 49.8(4) . . . . ?
C15 C10 C11 C12 0.3(4) . . . . ?
C1 N1 C8 C9 -177.7(2) . . . . ?
C1 N1 C8 C7 1.9(5) . . . . ?
C1 N1 C2 C3 178.0(3) . . . . ?
C1 C10 C15 C14 179.6(3) . . . . ?
C1 C10 C11 C12 -179.5(3) . . . . ?
C11 C10 C15 C14 -0.2(4) . . . . ?
C11 C10 C1 N1 -130.4(3) . . . . ?
C14 C13 C12 C11 0.0(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?

_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.610
