# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_g240329b_auto
_database_code_depnum_ccdc_archive 'CCDC 2425883'
loop_
_audit_author_name
_audit_author_address
'Juan Zhao'
;Soochow University
China
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-06-26 downloaded from the CCDC.
;
_audit_creation_date             2025-02-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        '2-(4-bromophenyl)isoquinolin-2-ium iodide'
_chemical_formula_moiety         'I, C15 H11 Br N'
_chemical_formula_sum            'C15 H11 Br I N'
_chemical_formula_weight         412.06
_chemical_melting_point          507.9
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'
I I -0.4742 1.8119 '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'

_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                   9.7506(11)
_cell_length_b                   11.3088(13)
_cell_length_c                   13.4947(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.994(12)
_cell_angle_gamma                90
_cell_volume                     1423.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    294.45(11)
_cell_measurement_theta_max      26.0810
_cell_measurement_theta_min      2.2280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.923
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8125
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.497
_diffrn_reflns_theta_min         2.290
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.45(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -10.00   1.00    1.00    --   12.87 -37.00 -90.00   52
  2  ω    -41.00 -14.00   1.00    1.00    --  -13.65  77.00 -30.00   27
  3  ω    -18.00  26.00   1.00    1.00    --  -13.65 -99.00  90.00   44
  4  ω    -38.00  43.00   1.00    1.00    --  -13.65  37.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080213000
_diffrn_orient_matrix_UB_12      -0.0544885000
_diffrn_orient_matrix_UB_13      -0.0237937000
_diffrn_orient_matrix_UB_21      -0.0110511000
_diffrn_orient_matrix_UB_22      -0.0310946000
_diffrn_orient_matrix_UB_23      0.0426776000
_diffrn_orient_matrix_UB_31      -0.0747973000
_diffrn_orient_matrix_UB_32      -0.0012527000
_diffrn_orient_matrix_UB_33      -0.0251184000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2330
_reflns_number_total             3752
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.656
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.191
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.036
_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)+(0.0442P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1190
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C11(H11), C7(H7), C6(H6), C14(H14), C13(H13), C1(H1),
 C9(H9), C2(H2), C3(H3)
;
_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
I1 I 0.42126(4) 0.42914(4) 0.21520(3) 0.04871(16) Uani 1 1 d . . . . .
Br1 Br 0.22196(6) 0.13971(6) 0.61068(5) 0.04846(19) Uani 1 1 d . . . . .
N1 N 0.7169(5) 0.2825(4) 0.4474(3) 0.0398(11) Uani 1 1 d . . . . .
C5 C 0.8565(5) 0.4267(5) 0.3906(4) 0.0372(12) Uani 1 1 d . . . . .
C8 C 0.7394(5) 0.3941(5) 0.4259(4) 0.0391(13) Uani 1 1 d . . . . .
H8 H 0.676249 0.452263 0.434377 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4610(6) 0.2805(5) 0.6040(4) 0.0441(14) Uani 1 1 d . . . . .
H12 H 0.445014 0.319403 0.660317 0.053 Uiso 1 1 calc R U . . .
C4 C 0.9487(6) 0.3365(6) 0.3757(4) 0.0425(14) Uani 1 1 d . . . . .
C10 C 0.5961(5) 0.2523(5) 0.4849(4) 0.0390(13) Uani 1 1 d . . . . .
C11 C 0.5736(6) 0.3137(5) 0.5669(4) 0.0454(14) Uani 1 1 d . . . . .
H11 H 0.633032 0.376425 0.596929 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3732(6) 0.1893(5) 0.5565(4) 0.0406(13) Uani 1 1 d . . . . .
C7 C 0.9192(6) 0.2198(6) 0.3977(4) 0.0499(15) Uani 1 1 d . . . . .
H7 H 0.977916 0.158968 0.387435 0.060 Uiso 1 1 calc R U . . .
C6 C 0.8799(6) 0.5455(6) 0.3692(4) 0.0465(15) Uani 1 1 d . . . . .
H6 H 0.818094 0.604127 0.378788 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3930(7) 0.1298(6) 0.4726(4) 0.0528(16) Uani 1 1 d . . . . .
H14 H 0.331418 0.069047 0.441045 0.063 Uiso 1 1 calc R U . . .
C13 C 0.5057(7) 0.1622(6) 0.4363(5) 0.0539(16) Uani 1 1 d . . . . .
H13 H 0.520918 0.123595 0.379509 0.065 Uiso 1 1 calc R U . . .
C1 C 0.9934(7) 0.5741(6) 0.3344(5) 0.0535(16) Uani 1 1 d . . . . .
H1 H 1.009798 0.652556 0.320631 0.064 Uiso 1 1 calc R U . . .
C9 C 0.8076(6) 0.1943(6) 0.4332(5) 0.0523(16) Uani 1 1 d . . . . .
H9 H 0.791055 0.116313 0.448477 0.063 Uiso 1 1 calc R U . . .
C2 C 1.0856(6) 0.4852(7) 0.3194(5) 0.0558(17) Uani 1 1 d . . . . .
H2 H 1.161923 0.505788 0.294631 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0662(6) 0.3694(7) 0.3402(5) 0.0577(18) Uani 1 1 d . . . . .
H3 H 1.130069 0.312209 0.331123 0.069 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 C15 1.912(6) . ?
N1 C8 1.328(7) . ?
N1 C10 1.451(7) . ?
N1 C9 1.384(7) . ?
C5 C8 1.410(8) . ?
C5 C4 1.411(8) . ?
C5 C6 1.407(8) . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.385(8) . ?
C12 C15 1.374(7) . ?
C4 C7 1.401(9) . ?
C4 C3 1.415(9) . ?
C10 C11 1.378(8) . ?
C10 C13 1.382(8) . ?
C11 H11 0.9300 . ?
C15 C14 1.378(8) . ?
C7 H7 0.9300 . ?
C7 C9 1.343(9) . ?
C6 H6 0.9300 . ?
C6 C1 1.362(9) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(9) . ?
C13 H13 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.402(10) . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.365(10) . ?
C3 H3 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 C10 120.2(5) . . ?
C8 N1 C9 120.2(5) . . ?
C9 N1 C10 119.7(5) . . ?
C8 C5 C4 118.2(5) . . ?
C6 C5 C8 120.9(5) . . ?
C6 C5 C4 120.9(5) . . ?
N1 C8 C5 121.6(5) . . ?
N1 C8 H8 119.2 . . ?
C5 C8 H8 119.2 . . ?
C11 C12 H12 120.4 . . ?
C15 C12 H12 120.4 . . ?
C15 C12 C11 119.1(5) . . ?
C5 C4 C3 118.1(6) . . ?
C7 C4 C5 118.2(5) . . ?
C7 C4 C3 123.7(6) . . ?
C11 C10 N1 119.8(5) . . ?
C11 C10 C13 121.6(5) . . ?
C13 C10 N1 118.6(5) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11 120.6 . . ?
C12 C15 Br1 119.1(4) . . ?
C12 C15 C14 122.1(6) . . ?
C14 C15 Br1 118.7(4) . . ?
C4 C7 H7 119.5 . . ?
C9 C7 C4 121.0(6) . . ?
C9 C7 H7 119.5 . . ?
C5 C6 H6 120.2 . . ?
C1 C6 C5 119.6(6) . . ?
C1 C6 H6 120.2 . . ?
C15 C14 H14 120.6 . . ?
C13 C14 C15 118.7(6) . . ?
C13 C14 H14 120.6 . . ?
C10 C13 H13 120.3 . . ?
C14 C13 C10 119.5(6) . . ?
C14 C13 H13 120.3 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.0(7) . . ?
C2 C1 H1 120.0 . . ?
N1 C9 H9 119.6 . . ?
C7 C9 N1 120.8(6) . . ?
C7 C9 H9 119.6 . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.7(6) . . ?
C3 C2 H2 119.2 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3 120.1 . . ?

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
Br1 C15 C14 C13 -177.2(5) . . . . ?
N1 C10 C11 C12 -177.5(5) . . . . ?
N1 C10 C13 C14 178.1(5) . . . . ?
C5 C4 C7 C9 -0.9(8) . . . . ?
C5 C4 C3 C2 -1.4(8) . . . . ?
C5 C6 C1 C2 0.5(9) . . . . ?
C8 N1 C10 C11 -50.4(7) . . . . ?
C8 N1 C10 C13 129.3(6) . . . . ?
C8 N1 C9 C7 0.0(8) . . . . ?
C8 C5 C4 C7 -0.5(7) . . . . ?
C8 C5 C4 C3 180.0(5) . . . . ?
C8 C5 C6 C1 -179.5(5) . . . . ?
C12 C15 C14 C13 0.9(9) . . . . ?
C4 C5 C8 N1 1.7(7) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
C4 C7 C9 N1 1.2(9) . . . . ?
C10 N1 C8 C5 179.3(5) . . . . ?
C10 N1 C9 C7 179.3(5) . . . . ?
C11 C12 C15 Br1 177.8(4) . . . . ?
C11 C12 C15 C14 -0.3(9) . . . . ?
C11 C10 C13 C14 -2.2(9) . . . . ?
C15 C12 C11 C10 -1.5(9) . . . . ?
C15 C14 C13 C10 0.4(9) . . . . ?
C7 C4 C3 C2 179.1(5) . . . . ?
C6 C5 C8 N1 -179.3(5) . . . . ?
C6 C5 C4 C7 -179.5(5) . . . . ?
C6 C5 C4 C3 0.9(8) . . . . ?
C6 C1 C2 C3 -1.0(9) . . . . ?
C13 C10 C11 C12 2.8(9) . . . . ?
C1 C2 C3 C4 1.4(9) . . . . ?
C9 N1 C8 C5 -1.4(8) . . . . ?
C9 N1 C10 C11 130.3(6) . . . . ?
C9 N1 C10 C13 -50.0(7) . . . . ?
C3 C4 C7 C9 178.6(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 3.001
_oxdiff_exptl_absorpt_empirical_full_min 0.577
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_r20230407a_autored
_database_code_depnum_ccdc_archive 'CCDC 2425884'
loop_
_audit_author_name
_audit_author_address
'Juan Zhao'
;Soochow University
China
;
_audit_update_record             
;
2025-02-21 deposited with the CCDC.	2025-06-26 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_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        (E)-3-methyl-N,2-di-p-tolylisoindolin-1-imine
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37
_chemical_melting_point          117.8
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.6041(3)
_cell_length_b                   10.4311(2)
_cell_length_c                   21.7838(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3318.47(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18303
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      31.5510
_cell_measurement_theta_min      1.9770
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45891
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.333
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00   0.00   0.00  360
  2  ω    -47.00  70.00   0.50    1.00    --  -20.00  70.00  90.00  234
  3  ω    -47.00  70.00   0.50    1.00    --  -20.00  70.00 180.00  234
  4  ω    -25.00  70.00   0.50    1.00    --  -20.00  70.00   0.00  190
  5  ω   -110.00 -15.00   0.50    1.00    --  -20.00 -70.00   0.00  190
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0319530000
_diffrn_orient_matrix_UB_12      -0.0101596000
_diffrn_orient_matrix_UB_13      0.0240327000
_diffrn_orient_matrix_UB_21      0.0356324000
_diffrn_orient_matrix_UB_22      0.0236235000
_diffrn_orient_matrix_UB_23      -0.0190021000
_diffrn_orient_matrix_UB_31      -0.0082331000
_diffrn_orient_matrix_UB_32      0.0629626000
_diffrn_orient_matrix_UB_33      0.0110165000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2930
_reflns_number_total             3390
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.140
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.073
_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)+(0.0564P)²+0.6356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00F(H00G), C00G(H00H), C00H(H00I),
 C00I(H00J), C00J(H00K), C00K(H00L), C00L(H00M), C00M(H00N), C00N(H00O),
 C005(H005), C009(H009)
2.c Idealised Me refined as rotating group:
 C00E(H00B,H00E,H00F)
;
_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
N001 N 0.62232(8) 0.75806(13) 0.76394(5) 0.0553(3) Uani 1 1 d . . . . .
N002 N 0.75924(8) 0.71199(13) 0.71364(5) 0.0578(3) Uani 1 1 d . . . . .
C00A C 0.53317(12) 0.61114(17) 0.57375(8) 0.0706(5) Uani 1 1 d . . . . .
H00A H 0.538111 0.580579 0.533779 0.085 Uiso 1 1 calc R U . . .
C00B C 0.66091(11) 0.79653(16) 0.82079(7) 0.0599(4) Uani 1 1 d . . . . .
C00C C 0.91301(13) 0.6133(2) 0.55854(9) 0.0803(5) Uani 1 1 d . . . . .
H00C H 0.947301 0.591650 0.524095 0.096 Uiso 1 1 calc R U . . .
C00D C 0.43757(11) 0.67534(16) 0.65767(8) 0.0652(4) Uani 1 1 d . . . . .
H00D H 0.379768 0.687884 0.674551 0.078 Uiso 1 1 calc R U . . .
C00E C 0.47651(11) 0.88097(16) 0.76476(9) 0.0684(4) Uani 1 1 d . . . . .
H00B H 0.487959 0.910333 0.805817 0.103 Uiso 1 1 calc R U . . .
H00E H 0.411729 0.872307 0.758534 0.103 Uiso 1 1 calc R U . . .
H00F H 0.500750 0.941830 0.735975 0.103 Uiso 1 1 calc R U . . .
C00F C 0.89416(13) 0.52360(19) 0.60234(8) 0.0763(5) Uani 1 1 d . . . . .
H00G H 0.916117 0.440466 0.597741 0.092 Uiso 1 1 calc R U . . .
C00G C 0.82935(12) 0.76799(17) 0.61639(7) 0.0647(4) Uani 1 1 d . . . . .
H00H H 0.808680 0.851781 0.620949 0.078 Uiso 1 1 calc R U . . .
C00H C 0.88088(13) 0.7354(2) 0.56590(8) 0.0776(5) Uani 1 1 d . . . . .
H00I H 0.894019 0.797231 0.536413 0.093 Uiso 1 1 calc R U . . .
C00I C 0.44764(12) 0.62939(18) 0.59876(9) 0.0741(5) Uani 1 1 d . . . . .
H00J H 0.395902 0.610444 0.575583 0.089 Uiso 1 1 calc R U . . .
C00J C 0.72969(12) 0.8858(2) 0.82326(9) 0.0764(5) Uani 1 1 d . . . . .
H00K H 0.752325 0.922181 0.787360 0.092 Uiso 1 1 calc R U . . .
C00K C 0.76519(15) 0.9214(3) 0.87976(12) 0.1053(8) Uani 1 1 d . . . . .
H00L H 0.812206 0.981365 0.881545 0.126 Uiso 1 1 calc R U . . .
C00L C 0.62667(17) 0.7467(2) 0.87455(8) 0.0944(7) Uani 1 1 d . . . . .
H00M H 0.578913 0.687796 0.873347 0.113 Uiso 1 1 calc R U . . .
C00M C 0.7320(2) 0.8694(3) 0.93283(11) 0.1222(11) Uani 1 1 d . . . . .
H00N H 0.756832 0.892825 0.970516 0.147 Uiso 1 1 calc R U . . .
C00N C 0.6628(3) 0.7837(3) 0.93007(10) 0.1239(10) Uani 1 1 d . . . . .
H00O H 0.639320 0.749325 0.966165 0.149 Uiso 1 1 calc R U . . .
C003 C 0.60249(9) 0.68362(13) 0.66616(6) 0.0473(3) Uani 1 1 d . . . . .
C004 C 0.67168(9) 0.71763(13) 0.71346(6) 0.0476(3) Uani 1 1 d . . . . .
C005 C 0.61204(11) 0.63722(15) 0.60672(7) 0.0571(4) Uani 1 1 d . . . . .
H005 H 0.669632 0.624095 0.589617 0.069 Uiso 1 1 calc R U . . .
C006 C 0.80796(9) 0.67736(14) 0.66047(6) 0.0499(3) Uani 1 1 d . . . . .
C007 C 0.51589(9) 0.70230(13) 0.69103(7) 0.0512(3) Uani 1 1 d . . . . .
C008 C 0.52252(9) 0.75197(14) 0.75521(7) 0.0538(4) Uani 1 1 d . . . . .
H008 H 0.496329 0.689070 0.783643 0.065 Uiso 1 1 calc R U . . .
C009 C 0.84291(11) 0.55490(16) 0.65334(7) 0.0619(4) Uani 1 1 d . . . . .
H009 H 0.831715 0.493176 0.683219 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
N001 C00B 1.4187(19) . ?
N001 C004 1.3808(17) . ?
N001 C008 1.4712(17) . ?
N002 C004 1.2801(18) . ?
N002 C006 1.4066(17) . ?
C00A H00A 0.9300 . ?
C00A C00I 1.376(3) . ?
C00A C005 1.384(2) . ?
C00B C00J 1.371(2) . ?
C00B C00L 1.375(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.365(3) . ?
C00C C00H 1.367(3) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.378(3) . ?
C00D C007 1.384(2) . ?
C00E H00B 0.9600 . ?
C00E H00E 0.9600 . ?
C00E H00F 0.9600 . ?
C00E C008 1.518(2) . ?
C00F H00G 0.9300 . ?
C00F C009 1.379(2) . ?
C00G H00H 0.9300 . ?
C00G C00H 1.375(2) . ?
C00G C006 1.383(2) . ?
C00H H00I 0.9300 . ?
C00I H00J 0.9300 . ?
C00J H00K 0.9300 . ?
C00J C00K 1.386(3) . ?
C00K H00L 0.9300 . ?
C00K C00M 1.366(4) . ?
C00L H00M 0.9300 . ?
C00L C00N 1.375(3) . ?
C00M H00N 0.9300 . ?
C00M C00N 1.350(4) . ?
C00N H00O 0.9300 . ?
C003 C004 1.4860(19) . ?
C003 C005 1.389(2) . ?
C003 C007 1.3896(19) . ?
C005 H005 0.9300 . ?
C006 C009 1.384(2) . ?
C007 C008 1.494(2) . ?
C008 H008 0.9800 . ?
C009 H009 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
C00B N001 C008 121.24(12) . . ?
C004 N001 C00B 125.05(12) . . ?
C004 N001 C008 113.64(11) . . ?
C004 N002 C006 120.97(12) . . ?
C00I C00A H00A 119.2 . . ?
C00I C00A C005 121.51(16) . . ?
C005 C00A H00A 119.2 . . ?
C00J C00B N001 121.17(15) . . ?
C00J C00B C00L 119.32(17) . . ?
C00L C00B N001 119.48(17) . . ?
C00F C00C H00C 120.4 . . ?
C00F C00C C00H 119.20(16) . . ?
C00H C00C H00C 120.4 . . ?
C00I C00D H00D 120.9 . . ?
C00I C00D C007 118.14(15) . . ?
C007 C00D H00D 120.9 . . ?
H00B C00E H00E 109.5 . . ?
H00B C00E H00F 109.5 . . ?
H00E C00E H00F 109.5 . . ?
C008 C00E H00B 109.5 . . ?
C008 C00E H00E 109.5 . . ?
C008 C00E H00F 109.5 . . ?
C00C C00F H00G 119.7 . . ?
C00C C00F C009 120.70(17) . . ?
C009 C00F H00G 119.7 . . ?
C00H C00G H00H 119.7 . . ?
C00H C00G C006 120.66(16) . . ?
C006 C00G H00H 119.7 . . ?
C00C C00H C00G 120.78(17) . . ?
C00C C00H H00I 119.6 . . ?
C00G C00H H00I 119.6 . . ?
C00A C00I C00D 120.92(15) . . ?
C00A C00I H00J 119.5 . . ?
C00D C00I H00J 119.5 . . ?
C00B C00J H00K 120.3 . . ?
C00B C00J C00K 119.4(2) . . ?
C00K C00J H00K 120.3 . . ?
C00J C00K H00L 119.6 . . ?
C00M C00K C00J 120.9(3) . . ?
C00M C00K H00L 119.6 . . ?
C00B C00L H00M 119.9 . . ?
C00N C00L C00B 120.2(3) . . ?
C00N C00L H00M 119.9 . . ?
C00K C00M H00N 120.3 . . ?
C00N C00M C00K 119.4(2) . . ?
C00N C00M H00N 120.3 . . ?
C00L C00N H00O 119.6 . . ?
C00M C00N C00L 120.8(3) . . ?
C00M C00N H00O 119.6 . . ?
C005 C003 C004 131.37(13) . . ?
C005 C003 C007 120.24(13) . . ?
C007 C003 C004 108.37(12) . . ?
N001 C004 C003 105.67(11) . . ?
N002 C004 N001 122.21(12) . . ?
N002 C004 C003 132.10(12) . . ?
C00A C005 C003 117.93(14) . . ?
C00A C005 H005 121.0 . . ?
C003 C005 H005 121.0 . . ?
C00G C006 N002 120.69(14) . . ?
C00G C006 C009 118.01(13) . . ?
C009 C006 N002 121.06(13) . . ?
C00D C007 C003 121.27(14) . . ?
C00D C007 C008 127.98(14) . . ?
C003 C007 C008 110.75(12) . . ?
N001 C008 C00E 112.49(13) . . ?
N001 C008 C007 101.54(11) . . ?
N001 C008 H008 109.5 . . ?
C00E C008 H008 109.5 . . ?
C007 C008 C00E 114.00(13) . . ?
C007 C008 H008 109.5 . . ?
C00F C009 C006 120.60(15) . . ?
C00F C009 H009 119.7 . . ?
C006 C009 H009 119.7 . . ?

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
N001 C00B C00J C00K 179.62(17) . . . . ?
N001 C00B C00L C00N -179.5(2) . . . . ?
N002 C006 C009 C00F -177.00(15) . . . . ?
C00B N001 C004 N002 -0.4(2) . . . . ?
C00B N001 C004 C003 178.11(14) . . . . ?
C00B N001 C008 C00E 60.18(19) . . . . ?
C00B N001 C008 C007 -177.55(13) . . . . ?
C00B C00J C00K C00M -0.5(3) . . . . ?
C00B C00L C00N C00M 0.2(4) . . . . ?
C00C C00F C009 C006 1.3(3) . . . . ?
C00D C007 C008 N001 179.15(15) . . . . ?
C00D C007 C008 C00E -59.6(2) . . . . ?
C00F C00C C00H C00G -0.6(3) . . . . ?
C00G C006 C009 C00F -2.7(2) . . . . ?
C00H C00C C00F C009 0.4(3) . . . . ?
C00H C00G C006 N002 176.76(16) . . . . ?
C00H C00G C006 C009 2.5(2) . . . . ?
C00I C00A C005 C003 -0.4(3) . . . . ?
C00I C00D C007 C003 -0.1(2) . . . . ?
C00I C00D C007 C008 -179.72(15) . . . . ?
C00J C00B C00L C00N -1.7(3) . . . . ?
C00J C00K C00M C00N -1.0(4) . . . . ?
C00K C00M C00N C00L 1.2(4) . . . . ?
C00L C00B C00J C00K 1.9(3) . . . . ?
C003 C007 C008 N001 -0.50(16) . . . . ?
C003 C007 C008 C00E 120.71(14) . . . . ?
C004 N001 C00B C00J 51.0(2) . . . . ?
C004 N001 C00B C00L -131.25(18) . . . . ?
C004 N001 C008 C00E -122.71(14) . . . . ?
C004 N001 C008 C007 -0.44(16) . . . . ?
C004 N002 C006 C00G 84.51(19) . . . . ?
C004 N002 C006 C009 -101.37(17) . . . . ?
C004 C003 C005 C00A 178.38(15) . . . . ?
C004 C003 C007 C00D -178.49(13) . . . . ?
C004 C003 C007 C008 1.19(16) . . . . ?
C005 C00A C00I C00D 0.4(3) . . . . ?
C005 C003 C004 N001 -179.77(15) . . . . ?
C005 C003 C004 N002 -1.4(3) . . . . ?
C005 C003 C007 C00D 0.1(2) . . . . ?
C005 C003 C007 C008 179.77(13) . . . . ?
C006 N002 C004 N001 -176.39(14) . . . . ?
C006 N002 C004 C003 5.5(2) . . . . ?
C006 C00G C00H C00C -0.8(3) . . . . ?
C007 C00D C00I C00A -0.2(3) . . . . ?
C007 C003 C004 N001 -1.42(15) . . . . ?
C007 C003 C004 N002 176.91(15) . . . . ?
C007 C003 C005 C00A 0.2(2) . . . . ?
C008 N001 C00B C00J -132.25(16) . . . . ?
C008 N001 C00B C00L 45.5(2) . . . . ?
C008 N001 C004 N002 -177.39(14) . . . . ?
C008 N001 C004 C003 1.14(16) . . . . ?

_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 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.666
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
