# Supplementary Information (SI) for Chemical Science.
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 2345700'
loop_
_audit_author_name
_audit_author_address
'Debasish Mandal'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2024-08-19 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-08-17
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H32 N4 O2'
_chemical_formula_sum            'C38 H32 N4 O2'
_chemical_formula_weight         576.67
_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'
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                   7.2089(7)
_cell_length_b                   9.3281(9)
_cell_length_c                   11.0857(13)
_cell_angle_alpha                97.148(9)
_cell_angle_beta                 92.220(9)
_cell_angle_gamma                96.254(8)
_cell_volume                     734.23(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      21.12
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.2656
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1140 after correction.
The Ratio of minimum to maximum transmission is 0.3564.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1144
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18304
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.854
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -349.73  10.27   1.00   10.00  26.42 -22.85 -31.50    --   360
  2  ω    -80.86   6.14   1.00   10.00    --  -22.85  89.85-137.66   87
  3  ω   -127.56  18.44   1.00   10.00    --  -22.85 -59.25-135.92  146
  4  ω    -80.85   6.15   1.00   10.00    --  -22.85  89.85  18.34   87
  5  ω   -127.56  18.44   1.00   10.00    --  -22.85 -59.25  71.08  146
  6  ω    -80.85   6.15   1.00   10.00    --  -22.85  89.85 120.33   87
  7  ω   -127.56  18.44   1.00   10.00    --  -22.85 -59.25 -84.92  146
  8  ω   -127.56  18.44   1.00   10.00    --  -22.85 -59.25 122.08  146
  9  ω    -80.86   6.14   1.00   10.00    --  -22.85  89.85 171.34   87
 10  ω   -127.56  18.44   1.00   10.00    --  -22.85 -59.25  20.08  146
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2017
_reflns_number_total             2537
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0874
_refine_ls_restrained_S_all      1.071
_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)+(0.0691P)²+2.4270P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2197
_refine_ls_wR_factor_ref         0.2307
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Rotating group:
 O1(H1)
1.b Aromatic/amide H refined with riding coordinates:
 N1(H1A), C10(H10), C6(H6), C11(H11), C13(H13), C3(H3), C4(H4), C7(H7),
 C15(H15), C18(H18), C17(H17), C16(H16)
1.c Idealised Me refined as rotating group:
 C1(H1B,H1C,H1D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.7614(5) 0.0977(3) 0.8613(3) 0.0455(9) Uani 1 1 d . . . . .
H1 H 0.664862 0.093431 0.808954 0.055 Uiso 1 1 d R U . . .
N1 N 0.2779(4) 0.2078(3) 0.6033(3) 0.0242(7) Uani 1 1 d . . . . .
H1A H 0.315109 0.135007 0.637755 0.029 Uiso 1 1 calc R U . . .
N2 N 0.6250(5) 0.2952(4) 0.7387(3) 0.0317(8) Uani 1 1 d . . . . .
C9 C 0.1225(5) 0.1983(4) 0.5255(3) 0.0235(8) Uani 1 1 d . . . . .
C8 C -0.0046(5) 0.0675(4) 0.4826(3) 0.0217(8) Uani 1 1 d . . . . .
C5 C -0.1504(5) 0.0964(4) 0.3916(3) 0.0218(8) Uani 1 1 d . . . . .
C10 C 0.1130(5) 0.3367(4) 0.4918(4) 0.0275(9) Uani 1 1 d . . . . .
H10 H 0.020409 0.363777 0.438392 0.033 Uiso 1 1 calc R U . . .
C6 C -0.3238(5) 0.1357(4) 0.4269(4) 0.0271(9) Uani 1 1 d . . . . .
H6 H -0.352950 0.139939 0.509992 0.033 Uiso 1 1 calc R U . . .
C11 C 0.2657(5) 0.4289(4) 0.5514(4) 0.0310(9) Uani 1 1 d . . . . .
H11 H 0.294081 0.529583 0.545495 0.037 Uiso 1 1 calc R U . . .
C2 C -0.4152(6) 0.1643(4) 0.2199(4) 0.0309(9) Uani 1 1 d . . . . .
C13 C 0.5390(6) 0.3872(4) 0.6896(4) 0.0313(9) Uani 1 1 d . . . . .
H13 H 0.591838 0.486037 0.699977 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3668(5) 0.3478(4) 0.6196(4) 0.0272(9) Uani 1 1 d . . . . .
C3 C -0.2449(6) 0.1208(5) 0.1845(4) 0.0353(10) Uani 1 1 d . . . . .
H3 H -0.217764 0.113212 0.100900 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1137(6) 0.0882(4) 0.2689(4) 0.0286(9) Uani 1 1 d . . . . .
H4 H 0.002305 0.059924 0.242571 0.034 Uiso 1 1 calc R U . . .
C7 C -0.4544(6) 0.1688(4) 0.3419(4) 0.0309(9) Uani 1 1 d . . . . .
H7 H -0.571850 0.194690 0.367618 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8062(6) 0.3342(5) 0.7970(4) 0.0333(10) Uani 1 1 d . . . . .
C19 C 0.8745(6) 0.2262(5) 0.8583(4) 0.0364(10) Uani 1 1 d . . . . .
C15 C 0.9239(6) 0.4638(5) 0.7942(4) 0.0404(11) Uani 1 1 d . . . . .
H15 H 0.881592 0.537592 0.751870 0.048 Uiso 1 1 calc R U . . .
C18 C 1.0520(7) 0.2459(5) 0.9156(4) 0.0385(11) Uani 1 1 d . . . . .
H18 H 1.095112 0.171786 0.957253 0.046 Uiso 1 1 calc R U . . .
C17 C 1.1641(6) 0.3734(6) 0.9114(4) 0.0447(12) Uani 1 1 d . . . . .
H17 H 1.286541 0.386779 0.948991 0.054 Uiso 1 1 calc R U . . .
C1 C -0.5520(7) 0.2102(5) 0.1282(5) 0.0431(12) Uani 1 1 d . . . . .
H1B H -0.509723 0.308987 0.111581 0.065 Uiso 1 1 calc R U . . .
H1C H -0.676131 0.208291 0.161385 0.065 Uiso 1 1 calc R U . . .
H1D H -0.558316 0.143029 0.052388 0.065 Uiso 1 1 calc R U . . .
C16 C 1.0990(6) 0.4860(6) 0.8514(4) 0.0443(12) Uani 1 1 d . . . . .
H16 H 1.175629 0.575431 0.850821 0.053 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
O1 H1 0.8829 . ?
O1 C19 1.378(5) . ?
N1 H1A 0.8800 . ?
N1 C9 1.375(5) . ?
N1 C12 1.378(5) . ?
N2 C13 1.274(5) . ?
N2 C14 1.425(5) . ?
C9 C8 1.460(5) . ?
C9 C10 1.396(5) . ?
C8 C8 1.370(7) 2_556 ?
C8 C5 1.498(5) . ?
C5 C6 1.397(5) . ?
C5 C4 1.389(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.409(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(6) . ?
C2 C3 1.390(6) . ?
C2 C7 1.389(6) . ?
C2 C1 1.521(6) . ?
C13 H13 0.9500 . ?
C13 C12 1.426(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(6) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C14 C19 1.405(6) . ?
C14 C15 1.403(6) . ?
C19 C18 1.390(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.373(6) . ?
C18 H18 0.9500 . ?
C18 C17 1.370(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.423(7) . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C16 H16 0.9500 . ?

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
C19 O1 H1 109.1 . . ?
C9 N1 H1A 125.0 . . ?
C9 N1 C12 110.1(3) . . ?
C12 N1 H1A 125.0 . . ?
C13 N2 C14 121.5(4) . . ?
N1 C9 C8 126.7(3) . . ?
N1 C9 C10 106.9(3) . . ?
C10 C9 C8 126.4(3) . . ?
C9 C8 C5 111.7(3) . . ?
C8 C8 C9 126.0(4) 2_556 . ?
C8 C8 C5 122.3(4) 2_556 . ?
C6 C5 C8 121.6(3) . . ?
C4 C5 C8 120.2(3) . . ?
C4 C5 C6 118.1(3) . . ?
C9 C10 H10 126.3 . . ?
C9 C10 C11 107.5(3) . . ?
C11 C10 H10 126.3 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 H6 119.6 . . ?
C10 C11 H11 125.9 . . ?
C12 C11 C10 108.2(4) . . ?
C12 C11 H11 125.9 . . ?
C3 C2 C1 120.8(4) . . ?
C7 C2 C3 118.2(4) . . ?
C7 C2 C1 121.0(4) . . ?
N2 C13 H13 118.7 . . ?
N2 C13 C12 122.7(4) . . ?
C12 C13 H13 118.7 . . ?
N1 C12 C13 122.3(3) . . ?
C11 C12 N1 107.4(3) . . ?
C11 C12 C13 130.2(4) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.7(4) . . ?
C3 C4 H4 119.6 . . ?
C6 C7 H7 119.6 . . ?
C2 C7 C6 120.8(4) . . ?
C2 C7 H7 119.6 . . ?
C19 C14 N2 114.9(4) . . ?
C15 C14 N2 127.2(4) . . ?
C15 C14 C19 117.8(4) . . ?
O1 C19 C14 118.7(4) . . ?
O1 C19 C18 119.6(4) . . ?
C18 C19 C14 121.7(4) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C19 C18 H18 120.4 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.4 . . ?
C18 C17 H17 119.7 . . ?
C18 C17 C16 120.6(4) . . ?
C16 C17 H17 119.7 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C15 C16 C17 119.2(5) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?

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
O1 C19 C18 C17 179.5(4) . . . . ?
N1 C9 C8 C8 3.2(7) . . . 2_556 ?
N1 C9 C8 C5 -175.8(3) . . . . ?
N1 C9 C10 C11 -0.1(4) . . . . ?
N2 C13 C12 N1 2.1(7) . . . . ?
N2 C13 C12 C11 -173.0(4) . . . . ?
N2 C14 C19 O1 -2.6(6) . . . . ?
N2 C14 C19 C18 177.5(4) . . . . ?
N2 C14 C15 C16 -177.8(4) . . . . ?
C9 N1 C12 C11 0.3(4) . . . . ?
C9 N1 C12 C13 -175.8(4) . . . . ?
C9 C8 C5 C6 -92.1(4) . . . . ?
C9 C8 C5 C4 86.2(4) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C8 C9 C10 C11 -178.1(4) . . . . ?
C8 C8 C5 C6 88.8(6) 2_556 . . . ?
C8 C8 C5 C4 -92.8(5) 2_556 . . . ?
C8 C5 C6 C7 177.0(3) . . . . ?
C8 C5 C4 C3 -177.3(4) . . . . ?
C5 C6 C7 C2 -0.4(6) . . . . ?
C10 C9 C8 C8 -179.2(5) . . . 2_556 ?
C10 C9 C8 C5 1.8(5) . . . . ?
C10 C11 C12 N1 -0.4(5) . . . . ?
C10 C11 C12 C13 175.3(4) . . . . ?
C6 C5 C4 C3 1.2(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C13 N2 C14 C19 173.4(4) . . . . ?
C13 N2 C14 C15 -10.0(7) . . . . ?
C12 N1 C9 C8 177.9(4) . . . . ?
C12 N1 C9 C10 -0.1(4) . . . . ?
C3 C2 C7 C6 2.3(6) . . . . ?
C4 C5 C6 C7 -1.4(6) . . . . ?
C7 C2 C3 C4 -2.6(6) . . . . ?
C14 N2 C13 C12 173.2(4) . . . . ?
C14 C19 C18 C17 -0.6(7) . . . . ?
C14 C15 C16 C17 2.0(7) . . . . ?
C19 C14 C15 C16 -1.3(7) . . . . ?
C19 C18 C17 C16 1.3(7) . . . . ?
C15 C14 C19 O1 -179.5(4) . . . . ?
C15 C14 C19 C18 0.6(7) . . . . ?
C18 C17 C16 C15 -2.0(7) . . . . ?
C1 C2 C3 C4 175.6(4) . . . . ?
C1 C2 C7 C6 -175.8(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_6d
_database_code_depnum_ccdc_archive 'CCDC 2348084'
loop_
_audit_author_name
_audit_author_address
'Debasish Mandal'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2024-08-19 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-08-17
_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            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H34 N4 O2, 2(C2 F3 O2)'
_chemical_formula_sum            'C42 H34 F6 N4 O6'
_chemical_formula_weight         804.73
_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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   13.3398(8)
_cell_length_b                   12.3038(7)
_cell_length_c                   25.4069(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.608(5)
_cell_angle_gamma                90
_cell_volume                     4133.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2913
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      22.1610
_cell_measurement_theta_min      1.6250
_shelx_estimated_absorpt_T_max   1.00000
_shelx_estimated_absorpt_T_min   0.29758
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull pinkish red'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   pinkish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1083
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            31728
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.469
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -121.73  70.27   2.00   10.00  31.11 -18.16 -31.50    --    96
  2  φ    -38.27 177.73   2.00   10.00  72.69 -18.16  31.50    --   108
  3  ω   -122.88  23.12   2.00   10.00    --  -18.16 -59.25  71.08   73
  4  ω   -122.88  23.12   2.00   10.00    --  -18.16 -59.25  20.08   73
  5  φ    -95.42  88.58   2.00   10.00  23.19 -18.16 -59.25    --    92
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2256
_reflns_number_total             3616
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0740
_refine_ls_restrained_S_all      1.059
_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)+(0.0940P)²+4.2888P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2075
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1A), C7(H7), C18(H18), C10(H10), C5(H5), C14(H14), C2(H2A),
 C17(H17), C9(H9), C4(H4), C3(H3), C15(H15)
1.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
1.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6485(2) 0.5415(2) 0.51101(10) 0.0527(7) Uani 1 1 d . . . . .
H1 H 0.612884 0.525537 0.482258 0.079 Uiso 1 1 calc R U . . .
O3 O 0.46893(19) 0.3830(2) 0.40348(10) 0.0480(7) Uani 1 1 d . . . . .
O2 O 0.5488(2) 0.5435(2) 0.41451(11) 0.0581(8) Uani 1 1 d . . . . .
N2 N 0.6285(2) 0.7704(2) 0.66164(11) 0.0364(7) Uani 1 1 d . . . . .
H2 H 0.588395 0.725848 0.641571 0.044 Uiso 1 1 calc R U . . .
N1 N 0.7418(2) 0.6884(3) 0.57627(11) 0.0378(7) Uani 1 1 d . . . . .
H1A H 0.680941 0.661997 0.577860 0.045 Uiso 1 1 calc R U . . .
F3 F 0.4551(2) 0.4629(3) 0.29776(10) 0.0930(10) Uani 1 1 d . . . . .
F2 F 0.3314(2) 0.4981(3) 0.33741(13) 0.0987(11) Uani 1 1 d . . . . .
F1 F 0.4366(3) 0.6211(3) 0.33029(14) 0.1201(14) Uani 1 1 d . . . . .
C13 C 0.4188(3) 0.7935(3) 0.68085(13) 0.0367(9) Uani 1 1 d . . . . .
C7 C 0.7748(3) 0.7618(3) 0.61172(14) 0.0389(9) Uani 1 1 d . . . . .
H7 H 0.839748 0.791691 0.609351 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7243(3) 0.8004(3) 0.65257(13) 0.0371(9) Uani 1 1 d . . . . .
C11 C 0.6057(3) 0.8197(3) 0.70598(14) 0.0371(9) Uani 1 1 d . . . . .
C6 C 0.7948(3) 0.6472(3) 0.53540(13) 0.0378(9) Uani 1 1 d . . . . .
C12 C 0.5060(3) 0.8066(3) 0.72374(13) 0.0360(8) Uani 1 1 d . . . . .
C1 C 0.7434(3) 0.5708(3) 0.50127(15) 0.0422(9) Uani 1 1 d . . . . .
C18 C 0.3489(3) 0.7102(3) 0.68282(14) 0.0395(9) Uani 1 1 d . . . . .
H18 H 0.357091 0.659897 0.711431 0.047 Uiso 1 1 calc R U . . .
C10 C 0.6886(3) 0.8852(3) 0.72594(15) 0.0426(9) Uani 1 1 d . . . . .
H10 H 0.693740 0.928928 0.756988 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8905(3) 0.6824(3) 0.52725(14) 0.0424(9) Uani 1 1 d . . . . .
H5 H 0.924765 0.735902 0.549836 0.051 Uiso 1 1 calc R U . . .
C14 C 0.4071(3) 0.8632(3) 0.63723(15) 0.0442(10) Uani 1 1 d . . . . .
H14 H 0.455643 0.918695 0.634471 0.053 Uiso 1 1 calc R U . . .
C2 C 0.7888(3) 0.5282(3) 0.46029(15) 0.0451(10) Uani 1 1 d . . . . .
H2A H 0.753865 0.476174 0.437035 0.054 Uiso 1 1 calc R U . . .
C17 C 0.2668(3) 0.7002(3) 0.64285(15) 0.0447(10) Uani 1 1 d . . . . .
H17 H 0.219137 0.643476 0.644904 0.054 Uiso 1 1 calc R U . . .
C9 C 0.7612(3) 0.8744(3) 0.69231(15) 0.0433(10) Uani 1 1 d . . . . .
H9 H 0.824620 0.910589 0.695529 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9353(3) 0.6390(4) 0.48608(16) 0.0498(11) Uani 1 1 d . . . . .
H4 H 1.000849 0.662497 0.480393 0.060 Uiso 1 1 calc R U . . .
C16 C 0.2533(3) 0.7720(4) 0.60002(15) 0.0470(10) Uani 1 1 d . . . . .
C20 C 0.4894(3) 0.4778(4) 0.39109(16) 0.0430(9) Uani 1 1 d . . . . .
C3 C 0.8850(3) 0.5609(3) 0.45285(16) 0.0499(11) Uani 1 1 d . . . . .
H3 H 0.916839 0.530095 0.425046 0.060 Uiso 1 1 calc R U . . .
C15 C 0.3250(3) 0.8524(4) 0.59772(16) 0.0499(11) Uani 1 1 d . . . . .
H15 H 0.318031 0.901365 0.568538 0.060 Uiso 1 1 calc R U . . .
C21 C 0.4301(3) 0.5172(4) 0.33885(17) 0.0530(11) Uani 1 1 d . . . . .
C19 C 0.1632(3) 0.7625(4) 0.55815(17) 0.0605(12) Uani 1 1 d . . . . .
H19A H 0.181072 0.718567 0.528593 0.091 Uiso 1 1 calc R U . . .
H19B H 0.142287 0.835154 0.545194 0.091 Uiso 1 1 calc R U . . .
H19C H 0.107512 0.727695 0.573304 0.091 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
O1 H1 0.8400 . ?
O1 C1 1.371(4) . ?
O3 C20 1.247(5) . ?
O2 C20 1.229(5) . ?
N2 H2 0.8800 . ?
N2 C8 1.378(4) . ?
N2 C11 1.350(4) . ?
N1 H1A 0.8800 . ?
N1 C7 1.310(5) . ?
N1 C6 1.425(4) . ?
F3 C21 1.319(5) . ?
F2 C21 1.333(5) . ?
F1 C21 1.302(5) . ?
C13 C12 1.493(5) . ?
C13 C18 1.391(5) . ?
C13 C14 1.394(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.394(5) . ?
C8 C9 1.400(5) . ?
C11 C12 1.469(5) . ?
C11 C10 1.408(5) . ?
C6 C1 1.396(5) . ?
C6 C5 1.390(5) . ?
C12 C12 1.365(7) 2_656 ?
C1 C2 1.375(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.398(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.380(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.382(5) . ?
C17 H17 0.9500 . ?
C17 C16 1.394(6) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.391(6) . ?
C16 C15 1.383(6) . ?
C16 C19 1.500(5) . ?
C20 C21 1.531(6) . ?
C3 H3 0.9500 . ?
C15 H15 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C8 N2 H2 125.2 . . ?
C11 N2 H2 125.2 . . ?
C11 N2 C8 109.6(3) . . ?
C7 N1 H1A 116.8 . . ?
C7 N1 C6 126.3(3) . . ?
C6 N1 H1A 116.8 . . ?
C18 C13 C12 121.0(3) . . ?
C18 C13 C14 118.5(3) . . ?
C14 C13 C12 120.6(3) . . ?
N1 C7 H7 116.8 . . ?
N1 C7 C8 126.5(3) . . ?
C8 C7 H7 116.8 . . ?
N2 C8 C7 125.7(3) . . ?
N2 C8 C9 107.4(3) . . ?
C7 C8 C9 126.9(3) . . ?
N2 C11 C12 121.4(3) . . ?
N2 C11 C10 107.7(3) . . ?
C10 C11 C12 130.8(3) . . ?
C1 C6 N1 116.3(3) . . ?
C5 C6 N1 123.5(3) . . ?
C5 C6 C1 120.2(3) . . ?
C11 C12 C13 115.9(3) . . ?
C12 C12 C13 122.2(4) 2_656 . ?
C12 C12 C11 121.9(4) 2_656 . ?
O1 C1 C6 117.0(3) . . ?
O1 C1 C2 123.1(4) . . ?
C2 C1 C6 119.9(4) . . ?
C13 C18 H18 119.9 . . ?
C13 C18 C17 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C11 C10 H10 126.1 . . ?
C9 C10 C11 107.7(3) . . ?
C9 C10 H10 126.1 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.7 . . ?
C1 C2 H2A 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2A 119.9 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C8 C9 H9 126.2 . . ?
C10 C9 C8 107.5(3) . . ?
C10 C9 H9 126.2 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C3 C4 H4 119.8 . . ?
C17 C16 C19 120.8(4) . . ?
C15 C16 C17 117.9(3) . . ?
C15 C16 C19 121.3(4) . . ?
O3 C20 C21 114.2(4) . . ?
O2 C20 O3 129.9(4) . . ?
O2 C20 C21 115.9(4) . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
F3 C21 F2 103.9(4) . . ?
F3 C21 C20 111.7(3) . . ?
F2 C21 C20 111.2(4) . . ?
F1 C21 F3 109.6(4) . . ?
F1 C21 F2 104.8(4) . . ?
F1 C21 C20 114.7(4) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.7(4) . . . . ?
O3 C20 C21 F3 -66.4(5) . . . . ?
O3 C20 C21 F2 49.3(5) . . . . ?
O3 C20 C21 F1 168.0(4) . . . . ?
O2 C20 C21 F3 114.0(4) . . . . ?
O2 C20 C21 F2 -130.3(4) . . . . ?
O2 C20 C21 F1 -11.5(6) . . . . ?
N2 C8 C9 C10 2.1(4) . . . . ?
N2 C11 C12 C13 -32.9(5) . . . . ?
N2 C11 C12 C12 147.3(2) . . . 2_656 ?
N2 C11 C10 C9 0.4(4) . . . . ?
N1 C7 C8 N2 -2.4(6) . . . . ?
N1 C7 C8 C9 176.3(4) . . . . ?
N1 C6 C1 O1 -1.3(5) . . . . ?
N1 C6 C1 C2 179.1(3) . . . . ?
N1 C6 C5 C4 -179.0(3) . . . . ?
C13 C18 C17 C16 0.7(5) . . . . ?
C13 C14 C15 C16 -0.7(6) . . . . ?
C7 N1 C6 C1 -178.6(3) . . . . ?
C7 N1 C6 C5 -1.3(6) . . . . ?
C7 C8 C9 C10 -176.8(4) . . . . ?
C8 N2 C11 C12 177.0(3) . . . . ?
C8 N2 C11 C10 0.9(4) . . . . ?
C11 N2 C8 C7 177.1(3) . . . . ?
C11 N2 C8 C9 -1.9(4) . . . . ?
C11 C10 C9 C8 -1.5(4) . . . . ?
C6 N1 C7 C8 -178.3(3) . . . . ?
C6 C1 C2 C3 0.0(6) . . . . ?
C6 C5 C4 C3 0.3(6) . . . . ?
C12 C13 C18 C17 178.9(3) . . . . ?
C12 C13 C14 C15 -178.8(3) . . . . ?
C12 C11 C10 C9 -175.1(4) . . . . ?
C1 C6 C5 C4 -1.8(6) . . . . ?
C1 C2 C3 C4 -1.5(6) . . . . ?
C18 C13 C12 C11 131.0(4) . . . . ?
C18 C13 C12 C12 -49.1(4) . . . 2_656 ?
C18 C13 C14 C15 2.6(5) . . . . ?
C18 C17 C16 C15 1.2(5) . . . . ?
C18 C17 C16 C19 -178.2(4) . . . . ?
C10 C11 C12 C13 142.2(4) . . . . ?
C10 C11 C12 C12 -37.7(5) . . . 2_656 ?
C5 C6 C1 O1 -178.7(3) . . . . ?
C5 C6 C1 C2 1.7(6) . . . . ?
C5 C4 C3 C2 1.4(6) . . . . ?
C14 C13 C12 C11 -47.5(5) . . . . ?
C14 C13 C12 C12 132.4(3) . . . 2_656 ?
C14 C13 C18 C17 -2.6(5) . . . . ?
C17 C16 C15 C14 -1.2(6) . . . . ?
C19 C16 C15 C14 178.2(4) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 212 electrons were 
found in a volume of 568Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.5[CHCl3] per Asymmetric Unit 
which account for 232 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.367 0.250 141.9 52.6 '1 CHCl3'
2 0.000 0.633 0.750 141.9 52.6 '1 CHCl3'
3 0.500 0.133 0.750 141.9 52.6 '1 CHCl3'
4 0.500 0.867 0.250 141.9 52.6 '1 CHCl3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
;
####################################################################### 
# 
# 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_6b
_database_code_depnum_ccdc_archive 'CCDC 2368499'
loop_
_audit_author_name
_audit_author_address
'Debasish Mandal'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2024-08-19 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2024-08-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C19 H17 N3'
_chemical_formula_sum            'C19 H17 N3'
_chemical_formula_weight         287.367
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.295(2)
_cell_length_b                   9.499(2)
_cell_length_c                   10.348(2)
_cell_angle_alpha                79.673(10)
_cell_angle_beta                 65.183(8)
_cell_angle_gamma                63.713(9)
_cell_volume                     743.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2202
_cell_measurement_temperature    105.00
_cell_measurement_theta_max      21.12
_cell_measurement_theta_min      2.39
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.2656
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1709 before and 0.1140 after correction.
The Ratio of minimum to maximum transmission is 0.3564.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       needle
_exptl_crystal_F_000             304.170
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.1581
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19667
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9981
_diffrn_reflns_theta_full        25.1665
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.17
_diffrn_ambient_temperature      105.00
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -10
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1639
_reflns_number_total             2666
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3804
_refine_diff_density_min         -0.3871
_refine_diff_density_rms         0.1008
_refine_ls_d_res_high            0.8357
_refine_ls_d_res_low             9.3917
_refine_ls_goodness_of_fit_ref   1.0988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.0988
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+0.0619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1736
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
N1 N 0.6141(3) 0.6683(3) 0.2649(2) 0.0289(6) Uani 1.000000 .
N2 N 0.7500(3) 0.7193(3) -0.0380(2) 0.0320(6) Uani 1.000000 .
N3 N 0.9697(4) 0.4815(3) -0.2376(3) 0.0429(7) Uani 1.000000 .
C5 C 0.4317(3) 0.6228(3) 0.6637(3) 0.0261(7) Uani 1.000000 .
C8 C 0.5015(3) 0.5664(3) 0.5149(3) 0.0273(7) Uani 1.000000 .
C9 C 0.5694(3) 0.6699(3) 0.4093(3) 0.0282(7) Uani 1.000000 .
C12 C 0.6672(3) 0.7867(3) 0.2017(3) 0.0294(7) Uani 1.000000 .
C6 C 0.2541(3) 0.7158(3) 0.7325(3) 0.0312(7) Uani 1.000000 .
C10 C 0.5960(3) 0.7935(3) 0.4365(3) 0.0321(7) Uani 1.000000 .
C13 C 0.7252(3) 0.8121(3) 0.0525(3) 0.0315(7) Uani 1.000000 .
C14 C 0.8043(3) 0.7592(3) -0.1848(3) 0.0305(7) Uani 1.000000 .
C11 C 0.6557(4) 0.8656(3) 0.3073(3) 0.0328(7) Uani 1.000000 .
C3 C 0.4732(4) 0.6418(3) 0.8735(3) 0.0328(7) Uani 1.000000 .
C4 C 0.5387(4) 0.5892(3) 0.7363(3) 0.0310(7) Uani 1.000000 .
C7 C 0.1893(4) 0.7659(3) 0.8716(3) 0.0333(7) Uani 1.000000 .
C2 C 0.2962(4) 0.7299(3) 0.9452(3) 0.0329(7) Uani 1.000000 .
C15 C 0.9215(4) 0.6347(4) -0.2851(3) 0.0304(7) Uani 1.000000 .
C19 C 0.7470(4) 0.9120(4) -0.2341(3) 0.0362(8) Uani 1.000000 .
C16 C 0.9793(4) 0.6726(4) -0.4286(3) 0.0390(8) Uani 1.000000 .
C17 C 0.9247(4) 0.8253(4) -0.4738(3) 0.0435(9) Uani 1.000000 .
C1 C 0.2242(5) 0.7803(4) 1.0967(3) 0.0424(9) Uani 1.000000 .
C18 C 0.8057(4) 0.9467(4) -0.3761(3) 0.0441(8) Uani 1.000000 .
H1a H 0.179(4) 0.711(4) 1.162(3) 0.055(10) Uiso 1.000000 .
H4 H 0.6601(4) 0.5286(3) 0.6905(3) 0.0372(9) Uiso 1.000000 R
H3 H 0.5503(4) 0.6175(3) 0.9201(3) 0.0394(9) Uiso 1.000000 R
H7 H 0.0681(4) 0.8266(3) 0.9178(3) 0.0400(9) Uiso 1.000000 R
H6 H 0.1781(3) 0.7445(3) 0.6841(3) 0.0375(9) Uiso 1.000000 R
H19 H 0.6646(4) 0.9951(4) -0.1673(3) 0.0435(9) Uiso 1.000000 R
H18 H 0.7655(4) 1.0523(4) -0.4072(3) 0.0529(10) Uiso 1.000000 R
H17 H 0.9687(4) 0.8479(4) -0.5723(3) 0.0521(10) Uiso 1.000000 R
H16 H 1.0585(4) 0.5908(4) -0.4972(3) 0.0468(10) Uiso 1.000000 R
H10 H 0.5769(3) 0.8233(3) 0.5272(3) 0.0385(9) Uiso 1.000000 R
H13 H 0.7468(3) 0.9033(3) 0.0176(3) 0.0378(9) Uiso 1.000000 R
H11 H 0.6834(4) 0.9534(3) 0.2946(3) 0.0393(9) Uiso 1.000000 R
H1 H 0.6095(3) 0.6014(3) 0.2195(2) 0.0346(7) Uiso 1.000000 R
H1b H 0.315(4) 0.783(4) 1.130(3) 0.065(11) Uiso 1.000000 .
H1c H 0.126(4) 0.882(4) 1.118(3) 0.064(11) Uiso 1.000000 .
H3a H 0.946(5) 0.474(4) -0.129(4) 0.080(12) Uiso 1.000000 .
H3b H 1.081(6) 0.406(5) -0.307(4) 0.101(15) Uiso 1.000000 .


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
N1 C9 1.374(3) . ?
N1 C12 1.376(3) . ?
N1 H1 0.8800 . ?
N2 C13 1.281(3) . ?
N2 C14 1.423(3) . ?
N3 C15 1.382(4) . ?
N3 H3a 1.05(4) . ?
N3 H3b 1.00(4) . ?
C5 C8 1.492(4) . ?
C5 C6 1.400(4) . ?
C5 C4 1.385(4) . ?
C8 C8 1.365(5) 2_666 ?
C8 C9 1.465(4) . ?
C9 C10 1.397(4) . ?
C12 C13 1.420(4) . ?
C12 C11 1.375(4) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9500 . ?
C10 C11 1.397(4) . ?
C10 H10 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.419(4) . ?
C14 C19 1.389(4) . ?
C11 H11 0.9500 . ?
C3 C4 1.376(4) . ?
C3 C2 1.392(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C7 C2 1.388(4) . ?
C7 H7 0.9500 . ?
C2 C1 1.496(4) . ?
C15 C16 1.390(4) . ?
C19 C18 1.371(4) . ?
C19 H19 0.9500 . ?
C16 C17 1.372(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C1 H1a 0.96(3) . ?
C1 H1b 1.04(4) . ?
C1 H1c 0.97(3) . ?
C18 H18 0.9500 . ?

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
C12 N1 C9 110.0(2) . . ?
H1 N1 C9 125.01(15) . . ?
H1 N1 C12 125.01(15) . . ?
C14 N2 C13 118.8(2) . . ?
H3a N3 C15 112.6(19) . . ?
H3b N3 C15 113(2) . . ?
H3b N3 H3a 120(3) . . ?
C6 C5 C8 120.1(2) . . ?
C4 C5 C8 121.9(2) . . ?
C4 C5 C6 118.0(2) . . ?
C8 C8 C5 122.3(3) 2_666 . ?
C9 C8 C5 112.2(2) . . ?
C8 C9 N1 127.0(2) . . ?
C10 C9 N1 106.4(2) . . ?
C10 C9 C8 126.6(2) . . ?
C13 C12 N1 122.9(3) . . ?
C11 C12 N1 107.7(2) . . ?
C11 C12 C13 129.5(3) . . ?
C7 C6 C5 119.9(3) . . ?
H6 C6 C5 120.05(16) . . ?
H6 C6 C7 120.05(17) . . ?
C11 C10 C9 108.1(2) . . ?
H10 C10 C9 125.93(16) . . ?
H10 C10 C11 125.93(16) . . ?
C12 C13 N2 123.9(3) . . ?
H13 C13 N2 118.06(17) . . ?
H13 C13 C12 118.06(17) . . ?
C15 C14 N2 117.6(3) . . ?
C19 C14 N2 123.6(3) . . ?
C19 C14 C15 118.9(3) . . ?
C10 C11 C12 107.8(3) . . ?
H11 C11 C12 126.10(16) . . ?
H11 C11 C10 126.10(16) . . ?
C2 C3 C4 121.3(3) . . ?
H3 C3 C4 119.37(17) . . ?
H3 C3 C2 119.37(17) . . ?
C3 C4 C5 121.5(3) . . ?
H4 C4 C5 119.27(16) . . ?
H4 C4 C3 119.27(17) . . ?
C2 C7 C6 122.0(3) . . ?
H7 C7 C6 118.98(17) . . ?
H7 C7 C2 118.98(16) . . ?
C7 C2 C3 117.3(3) . . ?
C1 C2 C3 121.1(3) . . ?
C1 C2 C7 121.6(3) . . ?
C14 C15 N3 119.2(3) . . ?
C16 C15 N3 122.7(3) . . ?
C16 C15 C14 118.0(3) . . ?
C18 C19 C14 122.0(3) . . ?
H19 C19 C14 118.98(17) . . ?
H19 C19 C18 119.0(2) . . ?
C17 C16 C15 121.7(3) . . ?
H16 C16 C15 119.15(19) . . ?
H16 C16 C17 119.15(19) . . ?
C18 C17 C16 120.3(3) . . ?
H17 C17 C16 119.85(19) . . ?
H17 C17 C18 119.85(19) . . ?
H1a C1 C2 112.0(19) . . ?
H1b C1 C2 114.7(17) . . ?
H1b C1 H1a 104(3) . . ?
H1c C1 C2 113(2) . . ?
H1c C1 H1a 104(3) . . ?
H1c C1 H1b 108(3) . . ?
C17 C18 C19 119.0(3) . . ?
H18 C18 C19 120.5(2) . . ?
H18 C18 C17 120.51(19) . . ?

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
N1 C9 C8 C5 -167.7(3) . . . . ?
N1 C9 C8 C8 11.7(3) . . . 2_666 ?
N1 C9 C10 C11 0.4(2) . . . . ?
N1 C12 C13 N2 -7.2(3) . . . . ?
N1 C12 C11 C10 0.4(2) . . . . ?
N2 C13 C12 C11 171.2(3) . . . . ?
N2 C14 C15 N3 3.6(3) . . . . ?
N2 C14 C15 C16 -178.2(2) . . . . ?
N2 C14 C19 C18 178.2(3) . . . . ?
N3 C15 C14 C19 -175.5(3) . . . . ?
N3 C15 C16 C17 177.6(3) . . . . ?
C5 C8 C8 C5 180.0(3) . . 2_666 2_666 ?
C5 C8 C8 C9 -0.6(3) . . 2_666 2_666 ?
C5 C8 C9 C10 10.0(3) . . . . ?
C5 C6 C7 C2 1.6(3) . . . . ?
C5 C4 C3 C2 0.5(3) . . . . ?
C8 C8 C9 C10 -170.6(3) 2_666 . . . ?
C8 C9 C10 C11 -177.7(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C6 C7 C2 C3 0.5(3) . . . . ?
C6 C7 C2 C1 -178.1(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C14 C19 C18 C17 0.6(3) . . . . ?
C15 C16 C17 C18 -1.6(3) . . . . ?
C19 C18 C17 C16 1.6(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
