# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_MM_147_OME_TP_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2069088'
loop_
_audit_author_name
_audit_author_address
'Manmath Mishra'
;Indian institute of Technology, Guwahati
India
;
_audit_update_record             
;
2021-03-11 deposited with the CCDC.	2022-05-30 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            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

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                   14.2857(15)
_cell_length_b                   5.8924(5)
_cell_length_c                   21.571(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.328(4)
_cell_angle_gamma                90
_cell_volume                     1815.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5009
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.10

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_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   none
_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            19935
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.393
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3187
_reflns_number_gt                2373
_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)+(0.1000P)²+0.2668P] 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         3187
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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
O2 O 0.26660(9) 0.03053(19) 0.71990(6) 0.0569(4) Uani 1 1 d . . . . .
O1 O 0.02307(10) 0.4845(3) 0.92351(6) 0.0715(4) Uani 1 1 d . . . . .
N1 N 0.22309(10) 0.3540(2) 0.66311(7) 0.0492(4) Uani 1 1 d . . . . .
N2 N 0.27666(11) 0.2849(3) 0.61441(7) 0.0541(4) Uani 1 1 d . . . . .
C16 C 0.46070(13) 0.2990(3) 0.67460(9) 0.0533(5) Uani 1 1 d . . . . .
H16 H 0.4181 0.4146 0.6822 0.064 Uiso 1 1 calc R U . . .
C8 C 0.22131(12) 0.2325(3) 0.71228(8) 0.0470(4) Uani 1 1 d . . . . .
C11 C 0.43259(12) 0.1121(3) 0.64049(8) 0.0471(4) Uani 1 1 d . . . . .
C7 C 0.16911(12) 0.3039(3) 0.76660(8) 0.0468(4) Uani 1 1 d . . . . .
C17 C 0.27522(13) 0.4243(3) 0.56184(8) 0.0519(5) Uani 1 1 d . . . . .
C10 C 0.33227(13) 0.0784(3) 0.61854(9) 0.0524(5) Uani 1 1 d . . . . .
H10 H 0.3328 0.0084 0.5773 0.063 Uiso 1 1 calc R U . . .
C22 C 0.20261(13) 0.5782(3) 0.55174(8) 0.0530(5) Uani 1 1 d . . . . .
H22 H 0.1537 0.5860 0.5794 0.064 Uiso 1 1 calc R U . . .
C15 C 0.55141(14) 0.3162(3) 0.69761(9) 0.0599(5) Uani 1 1 d . . . . .
H15 H 0.5696 0.4433 0.7205 0.072 Uiso 1 1 calc R U . . .
C9 C 0.28058(14) -0.0797(3) 0.66180(9) 0.0594(5) Uani 1 1 d . . . . .
H9A H 0.2205 -0.1211 0.6432 0.071 Uiso 1 1 calc R U . . .
H9B H 0.3167 -0.2173 0.6683 0.071 Uiso 1 1 calc R U . . .
C2 C 0.06934(13) 0.4361(3) 0.87031(9) 0.0550(5) Uani 1 1 d . . . . .
C5 C 0.11440(14) 0.4977(3) 0.76572(9) 0.0599(5) Uani 1 1 d . . . . .
H5 H 0.1113 0.5856 0.7299 0.072 Uiso 1 1 calc R U . . .
C14 C 0.61462(14) 0.1473(4) 0.68692(10) 0.0653(6) Uani 1 1 d . . . . .
H14 H 0.6755 0.1586 0.7028 0.078 Uiso 1 1 calc R U . . .
C6 C 0.17313(14) 0.1788(3) 0.82112(9) 0.0590(5) Uani 1 1 d . . . . .
H6 H 0.2094 0.0477 0.8230 0.071 Uiso 1 1 calc R U . . .
C12 C 0.49793(15) -0.0562(3) 0.62943(10) 0.0637(5) Uani 1 1 d . . . . .
H12 H 0.4806 -0.1823 0.6059 0.076 Uiso 1 1 calc R U . . .
C21 C 0.20309(16) 0.7195(4) 0.50062(9) 0.0661(6) Uani 1 1 d . . . . .
H21 H 0.1548 0.8237 0.4946 0.079 Uiso 1 1 calc R U . . .
C3 C 0.12466(14) 0.2445(3) 0.87234(9) 0.0642(5) Uani 1 1 d . . . . .
H3 H 0.1292 0.1594 0.9086 0.077 Uiso 1 1 calc R U . . .
C4 C 0.06440(14) 0.5639(3) 0.81657(9) 0.0628(5) Uani 1 1 d . . . . .
H4 H 0.0275 0.6939 0.8147 0.075 Uiso 1 1 calc R U . . .
C13 C 0.58781(15) -0.0390(4) 0.65270(11) 0.0705(6) Uani 1 1 d . . . . .
H13 H 0.6307 -0.1539 0.6453 0.085 Uiso 1 1 calc R U . . .
C18 C 0.34610(15) 0.4128(4) 0.51897(9) 0.0686(6) Uani 1 1 d . . . . .
H18 H 0.3947 0.3091 0.5245 0.082 Uiso 1 1 calc R U . . .
C1 C -0.03032(16) 0.6865(4) 0.92542(11) 0.0776(7) Uani 1 1 d . . . . .
H1A H 0.0097 0.8146 0.9187 0.116 Uiso 1 1 calc R U . . .
H1B H -0.0585 0.6999 0.9652 0.116 Uiso 1 1 calc R U . . .
H1C H -0.0784 0.6820 0.8936 0.116 Uiso 1 1 calc R U . . .
C20 C 0.27358(19) 0.7085(4) 0.45867(10) 0.0797(7) Uani 1 1 d . . . . .
H20 H 0.2732 0.8039 0.4243 0.096 Uiso 1 1 calc R U . . .
C19 C 0.34456(18) 0.5552(4) 0.46805(10) 0.0809(7) Uani 1 1 d . . . . .
H19 H 0.3925 0.5467 0.4397 0.097 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.363(2) . ?
O2 C9 1.430(2) . ?
O1 C2 1.368(2) . ?
O1 C1 1.415(2) . ?
N1 C8 1.280(2) . ?
N1 N2 1.376(2) . ?
N2 C17 1.400(2) . ?
N2 C10 1.454(2) . ?
C16 C11 1.379(2) . ?
C16 C15 1.381(3) . ?
C16 H16 0.9300 . ?
C8 C7 1.465(2) . ?
C11 C12 1.386(2) . ?
C11 C10 1.512(3) . ?
C7 C5 1.384(3) . ?
C7 C6 1.388(2) . ?
C17 C18 1.389(3) . ?
C17 C22 1.391(3) . ?
C10 C9 1.522(3) . ?
C10 H10 0.9800 . ?
C22 C21 1.382(3) . ?
C22 H22 0.9300 . ?
C15 C14 1.367(3) . ?
C15 H15 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 C3 1.378(3) . ?
C2 C4 1.383(3) . ?
C5 C4 1.379(3) . ?
C5 H5 0.9300 . ?
C14 C13 1.372(3) . ?
C14 H14 0.9300 . ?
C6 C3 1.373(3) . ?
C6 H6 0.9300 . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C21 C20 1.371(3) . ?
C21 H21 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C20 C19 1.370(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C9 111.49(14) . . ?
C2 O1 C1 118.13(16) . . ?
C8 N1 N2 119.28(14) . . ?
N1 N2 C17 116.55(14) . . ?
N1 N2 C10 120.90(14) . . ?
C17 N2 C10 122.55(15) . . ?
C11 C16 C15 120.65(17) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N1 C8 O2 124.74(16) . . ?
N1 C8 C7 121.47(15) . . ?
O2 C8 C7 113.79(14) . . ?
C16 C11 C12 118.31(17) . . ?
C16 C11 C10 122.28(15) . . ?
C12 C11 C10 119.30(16) . . ?
C5 C7 C6 117.55(17) . . ?
C5 C7 C8 121.59(16) . . ?
C6 C7 C8 120.86(16) . . ?
C18 C17 C22 118.68(17) . . ?
C18 C17 N2 120.91(17) . . ?
C22 C17 N2 120.41(16) . . ?
N2 C10 C11 114.95(14) . . ?
N2 C10 C9 106.11(14) . . ?
C11 C10 C9 110.98(15) . . ?
N2 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C9 C10 H10 108.2 . . ?
C21 C22 C17 120.02(19) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C14 C15 C16 120.27(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O2 C9 C10 109.83(14) . . ?
O2 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O1 C2 C3 115.61(17) . . ?
O1 C2 C4 125.00(17) . . ?
C3 C2 C4 119.39(18) . . ?
C4 C5 C7 121.68(18) . . ?
C4 C5 H5 119.2 . . ?
C7 C5 H5 119.2 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C3 C6 C7 121.32(17) . . ?
C3 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C13 C12 C11 120.83(18) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C20 C21 C22 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C6 C3 C2 120.34(18) . . ?
C6 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C2 119.71(18) . . ?
C5 C4 H4 120.1 . . ?
C2 C4 H4 120.1 . . ?
C12 C13 C14 120.21(19) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C19 C20 C21 119.1(2) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028



