# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mo_PK231_B_TP_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2290607'
loop_
_audit_author_name
_audit_author_address
'PALLAB KARJEE'
;IITGuwahati
India
;
_audit_update_record             
;
2023-08-24 deposited with the CCDC.	2024-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0187(6)
_cell_length_b                   15.8815(10)
_cell_length_c                   10.6953(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.728(2)
_cell_angle_gamma                90
_cell_volume                     1677.28(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7508
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      25.24

_exptl_crystal_description       Neddle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   none
_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            33086
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_max         28.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4177
_reflns_number_gt                2685
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1500P)²+0.5612P] 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         4177
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2209
_refine_ls_wR_factor_gt          0.1850
_refine_ls_goodness_of_fit_ref   0.853
_refine_ls_restrained_S_all      0.853
_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
N1 N 0.65100(16) 0.37151(10) 0.57973(15) 0.0479(4) Uani 1 1 d . . . . .
O2 O 0.5618(2) 0.37514(18) 0.97397(18) 0.1089(9) Uani 1 1 d . . . . .
C18 C 0.72878(19) 0.37903(12) 0.69775(18) 0.0463(5) Uani 1 1 d . . . . .
C7 C 0.40790(19) 0.34691(13) 0.47999(19) 0.0490(5) Uani 1 1 d . . . . .
C19 C 0.64176(19) 0.36750(13) 0.78551(19) 0.0487(5) Uani 1 1 d . . . . .
O1 O 0.7790(2) 0.3639(2) 0.9907(2) 0.1169(9) Uani 1 1 d . . . . .
C4 C 0.2786(2) 0.39643(14) 0.2829(2) 0.0580(5) Uani 1 1 d . . . . .
H4 H 0.2670 0.4358 0.2175 0.070 Uiso 1 1 calc R U . . .
C5 C 0.3865(2) 0.40527(13) 0.3812(2) 0.0548(5) Uani 1 1 d . . . . .
H5 H 0.4454 0.4506 0.3815 0.066 Uiso 1 1 calc R U . . .
C17 C 0.87347(19) 0.40043(13) 0.7061(2) 0.0501(5) Uani 1 1 d . . . . .
C2 C 0.1878(2) 0.33092(14) 0.2791(2) 0.0568(5) Uani 1 1 d . . . . .
C8 C 0.51736(19) 0.35655(13) 0.58985(19) 0.0495(5) Uani 1 1 d . . . . .
C6 C 0.3171(2) 0.28053(15) 0.4759(2) 0.0589(5) Uani 1 1 d . . . . .
H6 H 0.3286 0.2407 0.5406 0.071 Uiso 1 1 calc R U . . .
C20 C 0.6717(2) 0.36961(15) 0.9240(2) 0.0581(6) Uani 1 1 d . . . . .
C9 C 0.5109(2) 0.35323(14) 0.7162(2) 0.0537(5) Uani 1 1 d . . . . .
H9 H 0.4333 0.3432 0.7508 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9522(2) 0.43247(15) 0.8150(2) 0.0611(6) Uani 1 1 d . . . . .
H16 H 0.9141 0.4400 0.8877 0.073 Uiso 1 1 calc R U . . .
C3 C 0.2093(2) 0.27298(15) 0.3764(2) 0.0634(6) Uani 1 1 d . . . . .
H3 H 0.1501 0.2278 0.3754 0.076 Uiso 1 1 calc R U . . .
C12 C 0.9323(2) 0.39023(13) 0.5974(2) 0.0568(5) Uani 1 1 d . . . . .
C13 C 1.0676(2) 0.41266(16) 0.6016(3) 0.0688(7) Uani 1 1 d . . . . .
H13 H 1.1065 0.4070 0.5291 0.083 Uiso 1 1 calc R U . . .
C10 C 0.7054(2) 0.38296(17) 0.4626(2) 0.0611(6) Uani 1 1 d . . . . .
H10A H 0.7011 0.4420 0.4390 0.073 Uiso 1 1 calc R U . . .
H10B H 0.6514 0.3513 0.3946 0.073 Uiso 1 1 calc R U . . .
C11 C 0.8504(2) 0.35315(18) 0.4806(2) 0.0659(6) Uani 1 1 d . . . . .
H11A H 0.8526 0.2922 0.4870 0.079 Uiso 1 1 calc R U . . .
H11B H 0.8900 0.3690 0.4073 0.079 Uiso 1 1 calc R U . . .
C15 C 1.0866(2) 0.45330(16) 0.8170(3) 0.0718(7) Uani 1 1 d . . . . .
H15 H 1.1381 0.4745 0.8909 0.086 Uiso 1 1 calc R U . . .
C14 C 1.1443(2) 0.44289(16) 0.7106(3) 0.0744(7) Uani 1 1 d . . . . .
H14 H 1.2349 0.4563 0.7124 0.089 Uiso 1 1 calc R U . . .
C1 C 0.0688(3) 0.32329(18) 0.1736(3) 0.0790(8) Uani 1 1 d . . . . .
H1A H 0.0879 0.2817 0.1139 0.118 Uiso 1 1 calc R U . . .
H1B H 0.0522 0.3766 0.1316 0.118 Uiso 1 1 calc R U . . .
H1C H -0.0098 0.3066 0.2079 0.118 Uiso 1 1 calc R U . . .
C21 C 0.5806(4) 0.3770(3) 1.1108(3) 0.1288(17) Uani 1 1 d . . . . .
H21A H 0.6283 0.3273 1.1443 0.193 Uiso 1 1 calc R U . . .
H21B H 0.4939 0.3790 1.1376 0.193 Uiso 1 1 calc R U . . .
H21C H 0.6322 0.4260 1.1414 0.193 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
N1 C18 1.372(3) . ?
N1 C8 1.382(2) . ?
N1 C10 1.460(3) . ?
O2 C20 1.306(3) . ?
O2 C21 1.444(3) . ?
C18 C19 1.397(3) . ?
C18 C17 1.477(3) . ?
C7 C6 1.388(3) . ?
C7 C5 1.394(3) . ?
C7 C8 1.473(3) . ?
C19 C9 1.411(3) . ?
C19 C20 1.461(3) . ?
O1 C20 1.189(3) . ?
C4 C2 1.378(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C17 C16 1.389(3) . ?
C17 C12 1.398(3) . ?
C2 C3 1.379(3) . ?
C2 C1 1.502(3) . ?
C8 C9 1.364(3) . ?
C6 C3 1.387(3) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C16 C15 1.383(3) . ?
C16 H16 0.9300 . ?
C3 H3 0.9300 . ?
C12 C13 1.395(3) . ?
C12 C11 1.494(4) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C14 1.370(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C18 N1 C8 110.49(16) . . ?
C18 N1 C10 122.84(16) . . ?
C8 N1 C10 126.59(17) . . ?
C20 O2 C21 116.2(3) . . ?
N1 C18 C19 106.55(16) . . ?
N1 C18 C17 118.33(17) . . ?
C19 C18 C17 135.03(19) . . ?
C6 C7 C5 117.72(19) . . ?
C6 C7 C8 119.95(19) . . ?
C5 C7 C8 122.23(19) . . ?
C18 C19 C9 107.32(18) . . ?
C18 C19 C20 129.33(19) . . ?
C9 C19 C20 123.34(19) . . ?
C2 C4 C5 121.8(2) . . ?
C2 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C7 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C7 C5 H5 119.7 . . ?
C16 C17 C12 118.71(19) . . ?
C16 C17 C18 123.20(19) . . ?
C12 C17 C18 118.06(19) . . ?
C3 C2 C4 117.6(2) . . ?
C3 C2 C1 121.1(2) . . ?
C4 C2 C1 121.3(2) . . ?
C9 C8 N1 107.03(17) . . ?
C9 C8 C7 129.21(18) . . ?
N1 C8 C7 123.76(18) . . ?
C3 C6 C7 120.7(2) . . ?
C3 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
O1 C20 O2 119.9(2) . . ?
O1 C20 C19 128.1(2) . . ?
O2 C20 C19 112.0(2) . . ?
C8 C9 C19 108.60(19) . . ?
C8 C9 H9 125.7 . . ?
C19 C9 H9 125.7 . . ?
C15 C16 C17 120.9(2) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C2 C3 C6 121.5(2) . . ?
C2 C3 H3 119.2 . . ?
C6 C3 H3 119.2 . . ?
C13 C12 C17 119.1(2) . . ?
C13 C12 C11 121.4(2) . . ?
C17 C12 C11 119.44(19) . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
N1 C10 C11 110.01(18) . . ?
N1 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 C10 111.34(19) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
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 . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.044



