# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2142869'
loop_
_audit_author_name
_audit_author_address
'Veera Reddy Yatham'
;Indian Institute of Science Education and Research, Thiruvananthapuram
India
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39

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                   12.3306(9)
_cell_length_b                   15.8437(12)
_cell_length_c                   8.6085(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.257(3)
_cell_angle_gamma                90
_cell_volume                     1677.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25392
_cell_measurement_theta_min      1.656
_cell_measurement_theta_max      28.392

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.038
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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            25392
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.656
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4194
_reflns_number_gt                2013
_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       'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al. , 2008)'
_computing_publication_material  'WINZX (Farrugia, 2014) and PLATON(Spek, 2009)'
_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)+(0.0700P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4194
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.77317(11) 0.63970(9) 1.17779(15) 0.0687(4) Uani 1 1 d . . . . .
N1 N 0.79764(12) 0.44812(9) 0.55542(16) 0.0435(4) Uani 1 1 d . . . . .
O1 O 0.88786(11) 0.55109(10) 1.06078(17) 0.0772(5) Uani 1 1 d . . . . .
C13 C 0.81343(14) 0.39437(11) 0.43302(19) 0.0417(4) Uani 1 1 d . . . . .
C9 C 0.70285(14) 0.45149(11) 0.61259(19) 0.0405(4) Uani 1 1 d . . . . .
C10 C 0.61131(14) 0.40069(11) 0.55241(19) 0.0421(4) Uani 1 1 d . . . . .
C11 C 0.62568(14) 0.34524(11) 0.42746(19) 0.0432(5) Uani 1 1 d . . . . .
C12 C 0.73097(14) 0.34251(11) 0.3639(2) 0.0437(5) Uani 1 1 d . . . . .
C6 C 0.69346(14) 0.50894(12) 0.75142(19) 0.0441(5) Uani 1 1 d . . . . .
H6 H 0.620320 0.533514 0.743769 0.053 Uiso 1 1 calc R U . . .
C5 C 0.77521(15) 0.58075(11) 0.7561(2) 0.0488(5) Uani 1 1 d . . . . .
H5A H 0.763341 0.614489 0.662316 0.059 Uiso 1 1 calc R U . . .
H5B H 0.848221 0.557734 0.758706 0.059 Uiso 1 1 calc R U . . .
C4 C 0.76490(16) 0.63674(12) 0.8986(2) 0.0528(5) Uani 1 1 d . . . . .
H4A H 0.818728 0.681428 0.899807 0.063 Uiso 1 1 calc R U . . .
H4B H 0.693414 0.662603 0.892981 0.063 Uiso 1 1 calc R U . . .
C21 C 0.50933(15) 0.40287(13) 0.6159(2) 0.0528(5) Uani 1 1 d . . . . .
H21 H 0.498161 0.439712 0.697281 0.063 Uiso 1 1 calc R U . . .
C14 C 0.91671(15) 0.39287(12) 0.3761(2) 0.0536(5) Uani 1 1 d . . . . .
H14 H 0.971521 0.426968 0.421956 0.064 Uiso 1 1 calc R U . . .
C3 C 0.78137(16) 0.58554(13) 1.0460(2) 0.0539(5) Uani 1 1 d . . . . .
C18 C 0.53816(16) 0.29457(12) 0.3713(2) 0.0565(5) Uani 1 1 d . . . . .
H18 H 0.546700 0.258679 0.287614 0.068 Uiso 1 1 calc R U . . .
C7 C 0.70739(17) 0.45829(12) 0.9031(2) 0.0568(5) Uani 1 1 d . . . . .
H7A H 0.651154 0.415473 0.902816 0.068 Uiso 1 1 calc R U . . .
H7B H 0.777260 0.429888 0.908822 0.068 Uiso 1 1 calc R U . . .
C8 C 0.70088(17) 0.51428(13) 1.0456(2) 0.0612(6) Uani 1 1 d . . . . .
H8A H 0.627998 0.537189 1.046782 0.073 Uiso 1 1 calc R U . . .
H8B H 0.715214 0.480653 1.139022 0.073 Uiso 1 1 calc R U . . .
C20 C 0.42666(16) 0.35152(15) 0.5593(2) 0.0618(6) Uani 1 1 d . . . . .
H20 H 0.360065 0.353217 0.603324 0.074 Uiso 1 1 calc R U . . .
C19 C 0.44118(17) 0.29671(14) 0.4364(3) 0.0640(6) Uani 1 1 d . . . . .
H19 H 0.384675 0.261643 0.398879 0.077 Uiso 1 1 calc R U . . .
C17 C 0.75568(18) 0.29091(12) 0.2388(2) 0.0606(6) Uani 1 1 d . . . . .
H17 H 0.702120 0.256147 0.191600 0.073 Uiso 1 1 calc R U . . .
C15 C 0.93814(18) 0.34200(14) 0.2541(3) 0.0693(6) Uani 1 1 d . . . . .
H15 H 1.007111 0.341633 0.217080 0.083 Uiso 1 1 calc R U . . .
C1 C 0.9507(2) 0.5978(2) 1.1721(3) 0.0721(7) Uani 1 1 d . . . . .
C16 C 0.85699(19) 0.29100(14) 0.1856(3) 0.0728(7) Uani 1 1 d . . . . .
H16 H 0.871740 0.256460 0.102358 0.087 Uiso 1 1 calc R U . . .
C2 C 0.86878(19) 0.63068(17) 1.2756(3) 0.0812(7) Uani 1 1 d . . . . .
H2A H 0.857982 0.591246 1.359211 0.097 Uiso 1 1 calc R U . . .
H2B H 0.891651 0.684557 1.320368 0.097 Uiso 1 1 calc R U . . .
H1A H 1.006(2) 0.5635(15) 1.221(3) 0.087(8) Uiso 1 1 d . . . . .
H1B H 0.983(2) 0.643(2) 1.115(3) 0.132(12) Uiso 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
O2 C2 1.404(3) . ?
O2 C3 1.432(2) . ?
N1 C9 1.303(2) . ?
N1 C13 1.380(2) . ?
O1 C1 1.399(3) . ?
O1 C3 1.419(2) . ?
C13 C14 1.398(2) . ?
C13 C12 1.405(2) . ?
C9 C10 1.450(2) . ?
C9 C6 1.514(2) . ?
C10 C21 1.408(2) . ?
C10 C11 1.410(2) . ?
C11 C18 1.402(2) . ?
C11 C12 1.446(2) . ?
C12 C17 1.403(2) . ?
C6 C5 1.519(2) . ?
C6 C7 1.531(2) . ?
C6 H6 0.9800 . ?
C5 C4 1.527(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 C3 1.507(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C21 C20 1.366(3) . ?
C21 H21 0.9300 . ?
C14 C15 1.365(3) . ?
C14 H14 0.9300 . ?
C3 C8 1.503(3) . ?
C18 C19 1.358(3) . ?
C18 H18 0.9300 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C20 C19 1.391(3) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C17 C16 1.362(3) . ?
C17 H17 0.9300 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C1 C2 1.489(3) . ?
C1 H1A 0.95(2) . ?
C1 H1B 0.98(3) . ?
C16 H16 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C2 O2 C3 107.96(15) . . ?
C9 N1 C13 119.68(15) . . ?
C1 O1 C3 108.65(16) . . ?
N1 C13 C14 117.51(16) . . ?
N1 C13 C12 123.08(16) . . ?
C14 C13 C12 119.41(16) . . ?
N1 C9 C10 122.59(16) . . ?
N1 C9 C6 116.51(15) . . ?
C10 C9 C6 120.84(15) . . ?
C21 C10 C11 118.54(17) . . ?
C21 C10 C9 122.78(17) . . ?
C11 C10 C9 118.66(16) . . ?
C18 C11 C10 118.86(17) . . ?
C18 C11 C12 122.83(17) . . ?
C10 C11 C12 118.31(16) . . ?
C17 C12 C13 118.31(17) . . ?
C17 C12 C11 124.04(17) . . ?
C13 C12 C11 117.65(16) . . ?
C9 C6 C5 112.45(14) . . ?
C9 C6 C7 110.35(15) . . ?
C5 C6 C7 109.75(15) . . ?
C9 C6 H6 108.1 . . ?
C5 C6 H6 108.1 . . ?
C7 C6 H6 108.1 . . ?
C6 C5 C4 111.20(15) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C3 C4 C5 110.47(15) . . ?
C3 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C20 C21 C10 120.75(19) . . ?
C20 C21 H21 119.6 . . ?
C10 C21 H21 119.6 . . ?
C15 C14 C13 120.86(18) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O1 C3 O2 106.18(15) . . ?
O1 C3 C8 108.53(17) . . ?
O2 C3 C8 111.50(15) . . ?
O1 C3 C4 110.40(16) . . ?
O2 C3 C4 109.35(16) . . ?
C8 C3 C4 110.78(16) . . ?
C19 C18 C11 121.5(2) . . ?
C19 C18 H18 119.3 . . ?
C11 C18 H18 119.3 . . ?
C8 C7 C6 111.89(16) . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C3 C8 C7 111.44(16) . . ?
C3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C16 C17 C12 120.96(19) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C14 C15 C16 119.84(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
O1 C1 C2 103.2(2) . . ?
O1 C1 H1A 110.2(14) . . ?
C2 C1 H1A 116.0(14) . . ?
O1 C1 H1B 105.8(17) . . ?
C2 C1 H1B 111.5(17) . . ?
H1A C1 H1B 110(2) . . ?
C17 C16 C15 120.62(19) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O2 C2 C1 104.71(19) . . ?
O2 C2 H2A 110.8 . . ?
C1 C2 H2A 110.8 . . ?
O2 C2 H2B 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?

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
C9 N1 C13 C14 -179.81(17) . . . . ?
C9 N1 C13 C12 0.7(2) . . . . ?
C13 N1 C9 C10 -0.2(2) . . . . ?
C13 N1 C9 C6 177.26(14) . . . . ?
N1 C9 C10 C21 178.69(16) . . . . ?
C6 C9 C10 C21 1.4(2) . . . . ?
N1 C9 C10 C11 0.3(2) . . . . ?
C6 C9 C10 C11 -177.08(15) . . . . ?
C21 C10 C11 C18 0.0(2) . . . . ?
C9 C10 C11 C18 178.52(15) . . . . ?
C21 C10 C11 C12 -179.27(15) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
N1 C13 C12 C17 179.30(16) . . . . ?
C14 C13 C12 C17 -0.2(3) . . . . ?
N1 C13 C12 C11 -1.2(2) . . . . ?
C14 C13 C12 C11 179.30(16) . . . . ?
C18 C11 C12 C17 1.4(3) . . . . ?
C10 C11 C12 C17 -179.31(17) . . . . ?
C18 C11 C12 C13 -178.05(16) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
N1 C9 C6 C5 26.2(2) . . . . ?
C10 C9 C6 C5 -156.35(16) . . . . ?
N1 C9 C6 C7 -96.74(18) . . . . ?
C10 C9 C6 C7 80.75(19) . . . . ?
C9 C6 C5 C4 -179.11(15) . . . . ?
C7 C6 C5 C4 -55.9(2) . . . . ?
C6 C5 C4 C3 58.2(2) . . . . ?
C11 C10 C21 C20 1.0(3) . . . . ?
C9 C10 C21 C20 -177.45(17) . . . . ?
N1 C13 C14 C15 -179.25(18) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C1 O1 C3 O2 -14.5(2) . . . . ?
C1 O1 C3 C8 -134.5(2) . . . . ?
C1 O1 C3 C4 103.9(2) . . . . ?
C2 O2 C3 O1 -5.7(2) . . . . ?
C2 O2 C3 C8 112.4(2) . . . . ?
C2 O2 C3 C4 -124.78(19) . . . . ?
C5 C4 C3 O1 62.5(2) . . . . ?
C5 C4 C3 O2 179.01(15) . . . . ?
C5 C4 C3 C8 -57.7(2) . . . . ?
C10 C11 C18 C19 -1.2(3) . . . . ?
C12 C11 C18 C19 178.01(18) . . . . ?
C9 C6 C7 C8 178.77(15) . . . . ?
C5 C6 C7 C8 54.3(2) . . . . ?
O1 C3 C8 C7 -65.1(2) . . . . ?
O2 C3 C8 C7 178.33(15) . . . . ?
C4 C3 C8 C7 56.3(2) . . . . ?
C6 C7 C8 C3 -55.0(2) . . . . ?
C10 C21 C20 C19 -0.8(3) . . . . ?
C11 C18 C19 C20 1.5(3) . . . . ?
C21 C20 C19 C18 -0.4(3) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 -179.48(19) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C3 O1 C1 C2 27.5(3) . . . . ?
C12 C17 C16 C15 0.2(3) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C3 O2 C2 C1 22.1(3) . . . . ?
O1 C1 C2 O2 -30.3(3) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049

