# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_SB_C_210_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2334015'
loop_
_audit_author_name
_audit_author_address
'Subhamoy Biswas'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2024-02-20 deposited with the CCDC.	2024-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34

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                   12.5261(6)
_cell_length_b                   7.3772(4)
_cell_length_c                   16.8208(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.222(2)
_cell_angle_gamma                90
_cell_volume                     1538.39(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    8977
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.084
_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   ?
_diffrn_ambient_temperature      297(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            32704
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_full        25.044
_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             2718
_reflns_number_gt                1849
_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-2019/1 (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)+(0.0326P)²+1.1298P] 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         2718
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_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
O1 O 0.59964(17) 0.1764(3) 0.50100(12) 0.0653(6) Uani 1 1 d . . . . .
O2 O 0.63626(17) 0.3428(3) 0.25152(12) 0.0676(6) Uani 1 1 d . . . . .
N1 N 0.4844(2) 0.0721(3) 0.39561(15) 0.0620(7) Uani 1 1 d . . . . .
H1 H 0.466185 -0.014856 0.424967 0.074 Uiso 1 1 calc R U . . .
N2 N 0.58983(18) 0.3250(3) 0.38235(13) 0.0506(6) Uani 1 1 d . . . . .
C1 C 0.4643(2) 0.2157(4) 0.26703(17) 0.0523(7) Uani 1 1 d . . . . .
C2 C 0.4144(3) 0.2181(5) 0.18741(19) 0.0706(9) Uani 1 1 d . . . . .
H00E H 0.435132 0.305088 0.152602 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3357(3) 0.0955(5) 0.1590(2) 0.0793(11) Uani 1 1 d . . . . .
H3 H 0.303039 0.100151 0.105828 0.095 Uiso 1 1 calc R U . . .
C4 C 0.3055(3) -0.0342(5) 0.2101(2) 0.0760(10) Uani 1 1 d . . . . .
H4 H 0.251779 -0.117037 0.191341 0.091 Uiso 1 1 calc R U . . .
C5 C 0.3540(3) -0.0426(4) 0.2885(2) 0.0646(9) Uani 1 1 d . . . . .
H00C H 0.333328 -0.131024 0.322682 0.078 Uiso 1 1 calc R U . . .
C6 C 0.4340(2) 0.0814(4) 0.31679(18) 0.0516(7) Uani 1 1 d . . . . .
C7 C 0.5599(2) 0.1896(4) 0.42954(18) 0.0521(7) Uani 1 1 d . . . . .
C8 C 0.5473(2) 0.3564(4) 0.29656(17) 0.0511(7) Uani 1 1 d . . . . .
C9 C 0.5062(2) 0.5499(4) 0.28219(19) 0.0610(8) Uani 1 1 d . . . . .
H9 H 0.442350 0.551847 0.242038 0.073 Uiso 1 1 calc R U . . .
H00B H 0.488127 0.602042 0.331513 0.073 Uiso 1 1 calc R U . . .
C10 C 0.5964(3) 0.6546(5) 0.2533(2) 0.0858(11) Uani 1 1 d . . . . .
H10 H 0.568554 0.748524 0.215625 0.103 Uiso 1 1 calc R U . . .
H00L H 0.642920 0.709530 0.297904 0.103 Uiso 1 1 calc R U . . .
C11 C 0.6551(3) 0.5129(6) 0.2134(2) 0.0917(12) Uani 1 1 d . . . . .
H00M H 0.628159 0.507728 0.156452 0.110 Uiso 1 1 calc R U . . .
H00N H 0.731640 0.539778 0.219992 0.110 Uiso 1 1 calc R U . . .
C12 C 0.6694(2) 0.4514(4) 0.41993(16) 0.0502(7) Uani 1 1 d . . . . .
C13 C 0.6386(3) 0.5946(4) 0.46380(19) 0.0651(9) Uani 1 1 d . . . . .
H00D H 0.566758 0.607348 0.471108 0.078 Uiso 1 1 calc R U . . .
C14 C 0.7140(3) 0.7192(5) 0.4969(2) 0.0797(11) Uani 1 1 d . . . . .
H00G H 0.692275 0.816192 0.526073 0.096 Uiso 1 1 calc R U . . .
C15 C 0.8208(3) 0.7028(5) 0.4878(2) 0.0813(11) Uani 1 1 d . . . . .
C16 C 0.8495(3) 0.5599(6) 0.4444(2) 0.0875(12) Uani 1 1 d . . . . .
H16 H 0.921254 0.547257 0.436896 0.105 Uiso 1 1 calc R U . . .
C17 C 0.7754(3) 0.4334(5) 0.41113(19) 0.0699(10) Uani 1 1 d . . . . .
H00F H 0.797641 0.335649 0.382678 0.084 Uiso 1 1 calc R U . . .
C18 C 0.9024(4) 0.8398(7) 0.5266(3) 0.136(2) Uani 1 1 d . . . . .
H00O H 0.964654 0.838906 0.499311 0.204 Uiso 1 1 calc R U . . .
H00P H 0.923436 0.808652 0.582025 0.204 Uiso 1 1 calc R U . . .
H00Q H 0.870657 0.958510 0.522990 0.204 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 C7 1.237(3) . ?
O2 C8 1.438(3) . ?
O2 C11 1.444(4) . ?
N1 C7 1.348(4) . ?
N1 C6 1.386(4) . ?
N2 C7 1.362(3) . ?
N2 C12 1.443(3) . ?
N2 C8 1.483(3) . ?
C1 C6 1.385(4) . ?
C1 C2 1.394(4) . ?
C1 C8 1.503(4) . ?
C2 C3 1.373(5) . ?
C3 C4 1.374(5) . ?
C4 C5 1.373(4) . ?
C5 C6 1.390(4) . ?
C8 C9 1.525(4) . ?
C9 C10 1.505(4) . ?
C10 C11 1.491(5) . ?
C12 C17 1.364(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.378(5) . ?
C14 C15 1.373(5) . ?
C15 C16 1.360(5) . ?
C15 C18 1.517(5) . ?
C16 C17 1.377(5) . ?

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 C11 111.2(2) . . ?
C7 N1 C6 124.7(3) . . ?
C7 N2 C12 116.7(2) . . ?
C7 N2 C8 126.3(2) . . ?
C12 N2 C8 117.1(2) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 C8 122.1(3) . . ?
C2 C1 C8 120.2(3) . . ?
C3 C2 C1 121.7(3) . . ?
C2 C3 C4 119.3(3) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 C6 119.8(3) . . ?
C1 C6 N1 119.1(3) . . ?
C1 C6 C5 120.7(3) . . ?
N1 C6 C5 120.1(3) . . ?
O1 C7 N1 121.4(3) . . ?
O1 C7 N2 121.2(3) . . ?
N1 C7 N2 117.4(3) . . ?
O2 C8 N2 107.7(2) . . ?
O2 C8 C1 109.2(2) . . ?
N2 C8 C1 110.4(2) . . ?
O2 C8 C9 104.6(2) . . ?
N2 C8 C9 111.5(2) . . ?
C1 C8 C9 113.1(2) . . ?
C10 C9 C8 106.2(3) . . ?
C11 C10 C9 103.1(3) . . ?
O2 C11 C10 106.7(3) . . ?
C17 C12 C13 119.0(3) . . ?
C17 C12 N2 120.8(3) . . ?
C13 C12 N2 120.2(3) . . ?
C12 C13 C14 120.1(3) . . ?
C15 C14 C13 121.2(3) . . ?
C16 C15 C14 117.7(3) . . ?
C16 C15 C18 122.3(4) . . ?
C14 C15 C18 120.0(4) . . ?
C15 C16 C17 121.9(4) . . ?
C12 C17 C16 120.0(3) . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.037

