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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2520804'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2026-01-06 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N2 O2'
_chemical_formula_weight         330.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   5.4675(13)
_cell_length_b                   13.060(3)
_cell_length_c                   23.252(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.515(4)
_cell_angle_gamma                90
_cell_volume                     1652.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2678
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      20.67

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.594
_exptl_crystal_size_mid          0.381
_exptl_crystal_size_min          0.265
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9108
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS-2012/1 - Bruker AXS area detector 
 scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23859
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         25.254
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2997
_reflns_number_gt                1727
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0625P)²+0.5324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0092(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2997
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3884(5) 0.89073(19) 0.05792(11) 0.0504(7) Uani 1 1 d . . . . .
C2 C 0.2890(5) 0.80581(19) 0.08942(11) 0.0479(7) Uani 1 1 d . . . . .
C3 C 0.3805(5) 0.76972(19) 0.14060(12) 0.0523(7) Uani 1 1 d . . . . .
H3 H 0.287670 0.716486 0.153781 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5932(5) 0.79500(19) 0.18042(11) 0.0496(7) Uani 1 1 d . . . . .
C5 C 0.6344(6) 0.7290(2) 0.22685(12) 0.0626(8) Uani 1 1 d . . . . .
H5 H 0.526361 0.674721 0.229964 0.075 Uiso 1 1 calc R U . . .
C6 C 0.8298(6) 0.7403(3) 0.26892(13) 0.0734(9) Uani 1 1 d . . . . .
H6 H 0.853275 0.693417 0.299070 0.088 Uiso 1 1 calc R U . . .
C7 C 0.9858(6) 0.8197(3) 0.26585(12) 0.0692(9) Uani 1 1 d . . . . .
H7 H 1.114842 0.827737 0.294588 0.083 Uiso 1 1 calc R U . . .
C8 C 0.9573(5) 0.8912(2) 0.21972(11) 0.0553(7) Uani 1 1 d . . . . .
C9 C 0.7602(5) 0.87830(19) 0.17502(10) 0.0467(6) Uani 1 1 d . . . . .
C10 C 0.7519(5) 0.94977(18) 0.12832(10) 0.0475(6) Uani 1 1 d . . . . .
C11 C 0.9200(5) 1.0280(2) 0.12902(12) 0.0603(8) Uani 1 1 d . . . . .
H11 H 0.909809 1.074377 0.098529 0.072 Uiso 1 1 calc R U . . .
C12 C 1.1039(5) 1.0400(2) 0.17359(13) 0.0670(8) Uani 1 1 d . . . . .
H12 H 1.213934 1.094202 0.172928 0.080 Uiso 1 1 calc R U . . .
C13 C 1.1243(5) 0.9728(2) 0.21836(13) 0.0669(8) Uani 1 1 d . . . . .
H13 H 1.248927 0.980826 0.248167 0.080 Uiso 1 1 calc R U . . .
C14 C 0.0609(5) 0.7588(2) 0.05722(12) 0.0587(8) Uani 1 1 d . . . . .
H14A H -0.058106 0.813008 0.048398 0.070 Uiso 1 1 calc R U . . .
H14B H 0.105737 0.732155 0.020738 0.070 Uiso 1 1 calc R U . . .
C15 C 0.0269(3) 0.57690(10) 0.08952(8) 0.0523(7) Uani 1 1 d G . . . .
C16 C -0.0992(3) 0.50747(14) 0.12106(8) 0.0645(8) Uani 1 1 d G . . . .
H16 H -0.228789 0.529687 0.141016 0.077 Uiso 1 1 calc R U . . .
C17 C -0.0315(3) 0.40485(13) 0.12277(8) 0.0693(9) Uani 1 1 d G . . . .
H17 H -0.115874 0.358397 0.143870 0.083 Uiso 1 1 calc R U . . .
C18 C 0.1622(3) 0.37164(10) 0.09294(8) 0.0576(7) Uani 1 1 d G . . . .
C19 C 0.2883(3) 0.44107(13) 0.06141(8) 0.0664(8) Uani 1 1 d G . . . .
H19 H 0.417891 0.418850 0.041454 0.080 Uiso 1 1 calc R U . . .
C20 C 0.2206(3) 0.54369(12) 0.05970(8) 0.0683(9) Uani 1 1 d G . . . .
H20 H 0.304979 0.590141 0.038599 0.082 Uiso 1 1 calc R U . . .
C21 C 0.3982(6) 0.2290(2) 0.06555(16) 0.0870(11) Uani 1 1 d . . . . .
H21A H 0.367835 0.248875 0.025753 0.131 Uiso 1 1 calc R U . . .
H21B H 0.400601 0.155661 0.068273 0.131 Uiso 1 1 calc R U . . .
H21C H 0.553964 0.255842 0.081267 0.131 Uiso 1 1 calc R U . . .
N1 N 0.5869(4) 0.94620(17) 0.07778(10) 0.0534(6) Uani 1 1 d . . . . .
H1N H 0.626(5) 0.992(2) 0.0500(12) 0.064 Uiso 1 1 d . U . . .
N2 N -0.0567(4) 0.67858(19) 0.08617(12) 0.0669(8) Uani 1 1 d . . . . .
H2N H -0.146(6) 0.695(2) 0.1100(13) 0.080 Uiso 1 1 d . U . . .
O1 O 0.2854(4) 0.91282(14) 0.00951(8) 0.0698(6) Uani 1 1 d . . . . .
O2 O 0.2107(4) 0.26812(15) 0.09690(9) 0.0814(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.243(3) . ?
C1 N1 1.349(3) . ?
C1 C2 1.462(4) . ?
C2 C3 1.332(3) . ?
C2 C14 1.521(3) . ?
C3 C4 1.453(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 C9 1.434(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.349(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.420(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.406(4) . ?
C8 C9 1.433(3) . ?
C9 C10 1.429(3) . ?
C10 C11 1.374(4) . ?
C10 N1 1.412(3) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N2 1.431(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C15 N2 1.404(3) . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 O2 1.379(2) . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O2 1.410(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N1 H1N 0.92(3) . ?
N2 H2N 0.80(3) . ?

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
O1 C1 N1 117.7(2) . . ?
O1 C1 C2 118.1(2) . . ?
N1 C1 C2 124.2(2) . . ?
C3 C2 C1 126.2(2) . . ?
C3 C2 C14 121.1(2) . . ?
C1 C2 C14 112.7(2) . . ?
C2 C3 C4 134.3(3) . . ?
C2 C3 H3 112.9 . . ?
C4 C3 H3 112.9 . . ?
C5 C4 C9 118.9(3) . . ?
C5 C4 C3 114.6(2) . . ?
C9 C4 C3 126.4(2) . . ?
C4 C5 C6 122.8(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.5(3) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C13 C8 C7 119.4(3) . . ?
C13 C8 C9 121.2(3) . . ?
C7 C8 C9 119.4(3) . . ?
C10 C9 C8 116.1(2) . . ?
C10 C9 C4 126.0(2) . . ?
C8 C9 C4 117.8(2) . . ?
C11 C10 N1 114.1(2) . . ?
C11 C10 C9 120.3(2) . . ?
N1 C10 C9 125.6(2) . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
N2 C14 C2 116.6(2) . . ?
N2 C14 H14A 108.1 . . ?
C2 C14 H14A 108.1 . . ?
N2 C14 H14B 108.1 . . ?
C2 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 N2 118.10(15) . . ?
C20 C15 N2 121.79(15) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O2 C18 C19 124.94(16) . . ?
O2 C18 C17 115.05(16) . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C10 137.0(2) . . ?
C1 N1 H1N 110.1(17) . . ?
C10 N1 H1N 112.9(17) . . ?
C15 N2 C14 124.1(2) . . ?
C15 N2 H2N 115(2) . . ?
C14 N2 H2N 118(2) . . ?
C18 O2 C21 117.7(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
O1 C1 C2 C3 177.6(2) . . . . ?
N1 C1 C2 C3 -1.7(4) . . . . ?
O1 C1 C2 C14 -2.0(3) . . . . ?
N1 C1 C2 C14 178.7(2) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C14 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C4 C5 -173.1(3) . . . . ?
C2 C3 C4 C9 5.5(5) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 C6 179.3(3) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C6 C7 C8 C13 180.0(3) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C13 C8 C9 C10 2.9(3) . . . . ?
C7 C8 C9 C10 -176.4(2) . . . . ?
C13 C8 C9 C4 -178.1(2) . . . . ?
C7 C8 C9 C4 2.5(3) . . . . ?
C5 C4 C9 C10 176.4(2) . . . . ?
C3 C4 C9 C10 -2.2(4) . . . . ?
C5 C4 C9 C8 -2.5(3) . . . . ?
C3 C4 C9 C8 179.0(2) . . . . ?
C8 C9 C10 C11 -2.7(3) . . . . ?
C4 C9 C10 C11 178.4(2) . . . . ?
C8 C9 C10 N1 174.5(2) . . . . ?
C4 C9 C10 N1 -4.4(4) . . . . ?
N1 C10 C11 C12 -176.5(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C7 C8 C13 C12 178.0(3) . . . . ?
C9 C8 C13 C12 -1.4(4) . . . . ?
C3 C2 C14 N2 3.5(4) . . . . ?
C1 C2 C14 N2 -176.8(2) . . . . ?
C20 C15 C16 C17 0.0 . . . . ?
N2 C15 C16 C17 176.3(2) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 O2 -179.00(18) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
O2 C18 C19 C20 178.9(2) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C15 0.0 . . . . ?
C16 C15 C20 C19 0.0 . . . . ?
N2 C15 C20 C19 -176.2(2) . . . . ?
O1 C1 N1 C10 178.5(3) . . . . ?
C2 C1 N1 C10 -2.2(5) . . . . ?
C11 C10 N1 C1 -175.6(3) . . . . ?
C9 C10 N1 C1 7.0(5) . . . . ?
C16 C15 N2 C14 177.4(2) . . . . ?
C20 C15 N2 C14 -6.4(3) . . . . ?
C2 C14 N2 C15 -78.8(3) . . . . ?
C19 C18 O2 C21 -1.6(3) . . . . ?
C17 C18 O2 C21 177.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 O1 0.93 2.64 3.397(3) 139.1 3_675 yes
N1 H1N O1 0.92(3) 1.95(3) 2.876(3) 178(2) 3_675 yes

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_2054r
_database_code_depnum_ccdc_archive 'CCDC 2521104'
loop_
_audit_author_name
_audit_author_address
'Dr. D. Elias Jesu Packiam'
;IIT Madras
India
;
_audit_update_record             
;
2026-01-07 deposited with the CCDC.	2026-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19.54 N O'
_chemical_formula_weight         313.92

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8979(4)
_cell_length_b                   9.6890(5)
_cell_length_c                   10.6306(5)
_cell_angle_alpha                97.870(2)
_cell_angle_beta                 91.598(2)
_cell_angle_gamma                111.305(2)
_cell_volume                     842.81(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      25.03

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             333
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10106
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.941
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2982
_reflns_number_gt                2214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0749P)²+0.2290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2982
_refine_ls_number_parameters     245
_refine_ls_number_restraints     47
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1380
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2872(3) 0.7996(2) 0.4598(2) 0.0636(6) Uani 1 1 d . . . . .
C2 C 0.1541(3) 0.8449(3) 0.4466(3) 0.0755(7) Uani 1 1 d . . . . .
H2 H 0.075303 0.823710 0.504394 0.091 Uiso 1 1 calc R U . . .
C3 C 0.1406(3) 0.9188(3) 0.3505(3) 0.0744(7) Uani 1 1 d . . . . .
H3 H 0.055550 0.952433 0.344970 0.089 Uiso 1 1 calc R U . . .
C4 C 0.2530(2) 0.9448(2) 0.2601(2) 0.0606(6) Uani 1 1 d . . . . .
H4 H 0.239831 0.993061 0.193216 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3835(2) 0.90101(19) 0.26691(18) 0.0466(5) Uani 1 1 d . . . . .
C6 C 0.4080(2) 0.83033(19) 0.37080(18) 0.0490(5) Uani 1 1 d . . . . .
C7 C 0.5456(3) 0.7917(2) 0.39271(18) 0.0556(5) Uani 1 1 d . . . . .
C8 C 0.5540(3) 0.7201(3) 0.4935(2) 0.0794(7) Uani 1 1 d . . . . .
H8 H 0.642218 0.692186 0.506008 0.095 Uiso 1 1 calc R U . . .
C9 C 0.4329(4) 0.6878(4) 0.5783(3) 0.0993(10) Uani 1 1 d . . . . .
H9 H 0.441467 0.639363 0.646309 0.119 Uiso 1 1 calc R U . . .
C10 C 0.3038(4) 0.7268(3) 0.5616(2) 0.0900(9) Uani 1 1 d . . . . .
H10 H 0.224244 0.705051 0.618669 0.108 Uiso 1 1 calc R U . . .
C11 C 0.5701(2) 0.85919(19) 0.10184(18) 0.0454(4) Uani 1 1 d . . . . .
C12 C 0.6421(2) 0.7753(2) 0.17288(18) 0.0511(5) Uani 1 1 d D U . . .
C13 C 0.6852(2) 0.8343(2) 0.31190(19) 0.0585(5) Uani 1 1 d . . . . .
H13A H 0.765534 0.797957 0.342265 0.070 Uiso 1 1 calc R U . . .
H13B H 0.734478 0.942910 0.322826 0.070 Uiso 1 1 calc R U . . .
C17 C 0.9058(3) 0.4025(2) 0.1417(2) 0.0637(6) Uani 1 1 d . . . . .
C18 C 0.8695(3) 0.2510(3) 0.1023(2) 0.0702(6) Uani 1 1 d . . . . .
H18 H 0.776387 0.194936 0.048961 0.084 Uiso 1 1 calc R U . . .
C19 C 0.9694(4) 0.1824(3) 0.1412(3) 0.0804(7) Uani 1 1 d . . . . .
H19 H 0.944787 0.080963 0.112708 0.096 Uiso 1 1 calc R U . . .
C20 C 1.1044(3) 0.2625(3) 0.2215(3) 0.0811(8) Uani 1 1 d . . . . .
H20 H 1.171891 0.215802 0.247550 0.097 Uiso 1 1 calc R U . . .
C21 C 1.1400(3) 0.4099(3) 0.2632(3) 0.0787(7) Uani 1 1 d . . . . .
H21 H 1.231887 0.464367 0.318264 0.094 Uiso 1 1 calc R U . . .
C22 C 1.0415(3) 0.4794(3) 0.2247(2) 0.0730(7) Uani 1 1 d . . . . .
H22 H 1.066671 0.580491 0.255140 0.088 Uiso 1 1 calc R U . . .
N1 N 0.48270(18) 0.93190(16) 0.16444(15) 0.0486(4) Uani 1 1 d . . . . .
H1 H 0.488780 1.012722 0.136330 0.058 Uiso 1 1 calc R U . . .
O1 O 0.59616(18) 0.87376(15) -0.00991(13) 0.0602(4) Uani 1 1 d . . . . .
C14 C 0.6436(8) 0.6425(8) 0.1102(7) 0.0555(16) Uani 0.540(7) 1 d D U P A 1
H14A H 0.646373 0.645503 0.019472 0.067 Uiso 0.540(7) 1 calc R U P A 1
H14B H 0.546068 0.560515 0.123611 0.067 Uiso 0.540(7) 1 calc R U P A 1
C15 C 0.8090(7) 0.6141(6) 0.1661(4) 0.0645(15) Uani 0.540(7) 1 d D U P A 1
H15A H 0.907753 0.683009 0.139066 0.077 Uiso 0.540(7) 1 calc R U P A 1
H15B H 0.817117 0.624584 0.258410 0.077 Uiso 0.540(7) 1 calc R U P A 1
C16 C 0.7754(7) 0.4562(6) 0.1061(6) 0.0569(15) Uani 0.540(7) 1 d D U P A 1
H16A H 0.673576 0.391292 0.132119 0.068 Uiso 0.540(7) 1 calc R U P A 1
H16B H 0.764274 0.449240 0.014188 0.068 Uiso 0.540(7) 1 calc R U P A 1
C14' C 0.7084(9) 0.6883(8) 0.1088(7) 0.0462(15) Uani 0.460(7) 1 d D U P A 2
H14' H 0.760908 0.716297 0.036639 0.055 Uiso 0.460(7) 1 calc R U P A 2
C15' C 0.6983(8) 0.5291(7) 0.1568(5) 0.0573(17) Uani 0.460(7) 1 d D U P A 2
H15C H 0.723375 0.541059 0.247947 0.069 Uiso 0.460(7) 1 calc R U P A 2
H15D H 0.594625 0.448223 0.131177 0.069 Uiso 0.460(7) 1 calc R U P A 2
C16' C 0.8346(10) 0.5097(11) 0.0795(8) 0.073(2) Uani 0.460(7) 1 d D U P A 2
H16C H 0.919813 0.606654 0.079374 0.088 Uiso 0.460(7) 1 calc R U P A 2
H16D H 0.792825 0.466086 -0.007996 0.088 Uiso 0.460(7) 1 calc R U P A 2


_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
C1 C10 1.402(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.428(3) . ?
C2 C3 1.351(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.417(2) . ?
C5 C6 1.428(3) . ?
C6 C7 1.426(3) . ?
C7 C8 1.369(3) . ?
C7 C13 1.495(3) . ?
C8 C9 1.399(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.347(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.234(2) . ?
C11 N1 1.357(2) . ?
C11 C12 1.471(3) . ?
C12 C14' 1.322(8) . ?
C12 C14 1.370(7) . ?
C12 C13 1.495(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C17 C22 1.378(3) . ?
C17 C18 1.384(3) . ?
C17 C16 1.492(6) . ?
C17 C16' 1.599(8) . ?
C18 C19 1.373(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.351(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?
C14 C15 1.699(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.492(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14' C15' 1.663(8) . ?
C14' H14' 0.9300 . ?
C15' C16' 1.536(8) . ?
C15' H15C 0.9700 . ?
C15' H15D 0.9700 . ?
C16' H16C 0.9700 . ?
C16' H16D 0.9700 . ?

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
C10 C1 C2 120.5(2) . . ?
C10 C1 C6 119.3(2) . . ?
C2 C1 C6 120.2(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 121.7(2) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 N1 114.12(18) . . ?
C4 C5 C6 119.93(18) . . ?
N1 C5 C6 125.94(17) . . ?
C7 C6 C5 124.54(18) . . ?
C7 C6 C1 118.28(19) . . ?
C5 C6 C1 117.16(19) . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 C13 119.0(2) . . ?
C6 C7 C13 121.52(18) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C1 121.3(3) . . ?
C9 C10 H10 119.4 . . ?
C1 C10 H10 119.4 . . ?
O1 C11 N1 119.30(16) . . ?
O1 C11 C12 121.87(17) . . ?
N1 C11 C12 118.64(17) . . ?
C14' C12 C11 118.6(4) . . ?
C14 C12 C11 117.4(3) . . ?
C14' C12 C13 122.5(4) . . ?
C14 C12 C13 126.5(3) . . ?
C11 C12 C13 115.52(16) . . ?
C7 C13 C12 114.61(17) . . ?
C7 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C7 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C22 C17 C18 117.5(2) . . ?
C22 C17 C16 127.2(3) . . ?
C18 C17 C16 114.3(3) . . ?
C22 C17 C16' 113.5(4) . . ?
C18 C17 C16' 127.4(4) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 119.9(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 121.3(2) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C11 N1 C5 132.71(15) . . ?
C11 N1 H1 113.6 . . ?
C5 N1 H1 113.6 . . ?
C12 C14 C15 109.4(5) . . ?
C12 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C12 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C14 101.9(5) . . ?
C16 C15 H15A 111.4 . . ?
C14 C15 H15A 111.4 . . ?
C16 C15 H15B 111.4 . . ?
C14 C15 H15B 111.4 . . ?
H15A C15 H15B 109.3 . . ?
C17 C16 C15 112.5(4) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C12 C14' C15' 120.2(5) . . ?
C12 C14' H14' 119.9 . . ?
C15' C14' H14' 119.9 . . ?
C16' C15' C14' 95.7(6) . . ?
C16' C15' H15C 112.6 . . ?
C14' C15' H15C 112.6 . . ?
C16' C15' H15D 112.6 . . ?
C14' C15' H15D 112.6 . . ?
H15C C15' H15D 110.1 . . ?
C15' C16' C17 109.4(5) . . ?
C15' C16' H16C 109.8 . . ?
C17 C16' H16C 109.8 . . ?
C15' C16' H16D 109.8 . . ?
C17 C16' H16D 109.8 . . ?
H16C C16' H16D 108.2 . . ?

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
C10 C1 C2 C3 178.1(2) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 3.1(3) . . . . ?
C2 C3 C4 C5 -2.0(3) . . . . ?
C3 C4 C5 N1 177.96(19) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 -174.66(17) . . . . ?
N1 C5 C6 C7 5.8(3) . . . . ?
C4 C5 C6 C1 4.0(3) . . . . ?
N1 C5 C6 C1 -175.58(16) . . . . ?
C10 C1 C6 C7 -2.9(3) . . . . ?
C2 C1 C6 C7 175.82(18) . . . . ?
C10 C1 C6 C5 178.38(19) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
C5 C6 C7 C8 -178.08(19) . . . . ?
C1 C6 C7 C8 3.3(3) . . . . ?
C5 C6 C7 C13 5.0(3) . . . . ?
C1 C6 C7 C13 -173.62(17) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C13 C7 C8 C9 175.0(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C1 0.2(4) . . . . ?
C2 C1 C10 C9 -177.5(2) . . . . ?
C6 C1 C10 C9 1.2(4) . . . . ?
O1 C11 C12 C14' -14.0(4) . . . . ?
N1 C11 C12 C14' 171.1(4) . . . . ?
O1 C11 C12 C14 -42.6(4) . . . . ?
N1 C11 C12 C14 142.5(3) . . . . ?
O1 C11 C12 C13 145.58(19) . . . . ?
N1 C11 C12 C13 -29.3(3) . . . . ?
C8 C7 C13 C12 124.7(2) . . . . ?
C6 C7 C13 C12 -58.4(3) . . . . ?
C14' C12 C13 C7 -121.7(4) . . . . ?
C14 C12 C13 C7 -91.4(4) . . . . ?
C11 C12 C13 C7 79.6(2) . . . . ?
C22 C17 C18 C19 -2.5(4) . . . . ?
C16 C17 C18 C19 -172.2(4) . . . . ?
C16' C17 C18 C19 162.2(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C17 -1.0(4) . . . . ?
C18 C17 C22 C21 2.3(4) . . . . ?
C16 C17 C22 C21 170.5(4) . . . . ?
C16' C17 C22 C21 -164.5(3) . . . . ?
O1 C11 N1 C5 152.85(19) . . . . ?
C12 C11 N1 C5 -32.1(3) . . . . ?
C4 C5 N1 C11 -146.2(2) . . . . ?
C6 C5 N1 C11 33.4(3) . . . . ?
C11 C12 C14 C15 148.6(4) . . . . ?
C13 C12 C14 C15 -40.6(6) . . . . ?
C12 C14 C15 C16 170.3(4) . . . . ?
C22 C17 C16 C15 3.2(8) . . . . ?
C18 C17 C16 C15 171.7(4) . . . . ?
C14 C15 C16 C17 -179.7(4) . . . . ?
C11 C12 C14' C15' -145.8(5) . . . . ?
C13 C12 C14' C15' 56.1(7) . . . . ?
C12 C14' C15' C16' -162.7(6) . . . . ?
C14' C15' C16' C17 158.2(5) . . . . ?
C22 C17 C16' C15' -95.6(7) . . . . ?
C18 C17 C16' C15' 99.2(7) . . . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.042



