# 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 2020

####################################################################### 
# 
# 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_HYANTVAN_1_a
_database_code_depnum_ccdc_archive 'CCDC 1483217'
loop_
_audit_author_name
_audit_author_address
'SOMNATH KHANRA'
;THE UNIVERSITY OF BURDWAN
India
;
_audit_update_record             
;
2019-04-19 deposited with the CCDC.	2020-04-17 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            'C23 H18 N2 O2'
_chemical_formula_weight         354.39

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                   9.4580(12)
_cell_length_b                   9.6384(12)
_cell_length_c                   20.324(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.752(9)
_cell_angle_gamma                90
_cell_volume                     1820.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6389
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      22.03

_exptl_crystal_description       Plate
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.083
_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      293(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            18989
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.702
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4516
_reflns_number_gt                1674
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0639P)²+0.2770P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0010(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4516
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1927
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1840
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O001 O 0.2411(2) -0.2687(2) 0.20226(10) 0.0709(6) Uani 1 1 d . . . . .
H001 H 0.2889 -0.2825 0.1731 0.106 Uiso 1 1 calc R U . . .
O002 O 0.4445(2) -0.0988(2) 0.17265(10) 0.0814(7) Uani 1 1 d . . . . .
N5 N 0.6475(3) 0.1393(2) 0.40599(10) 0.0600(6) Uani 1 1 d . . . . .
N004 N 0.7047(3) 0.1938(2) 0.47002(11) 0.0685(7) Uani 1 1 d . . . . .
C005 C 0.4225(3) -0.0957(3) 0.23725(13) 0.0562(7) Uani 1 1 d . . . . .
C006 C 0.8579(3) 0.3667(3) 0.52991(13) 0.0562(7) Uani 1 1 d . . . . .
C007 C 0.3153(3) -0.1848(3) 0.25002(14) 0.0560(7) Uani 1 1 d . . . . .
C008 C 0.4650(3) -0.0213(3) 0.35140(14) 0.0588(7) Uani 1 1 d . . . . .
C009 C 0.7865(3) 0.2934(3) 0.46942(13) 0.0637(8) Uani 1 1 d . . . . .
H009 H 0.8039 0.3239 0.4282 0.076 Uiso 1 1 calc R U . . .
C00A C 0.8320(3) 0.5093(3) 0.53424(15) 0.0609(8) Uani 1 1 d . . . . .
C00B C 0.4958(3) -0.0147(3) 0.28718(14) 0.0620(8) Uani 1 1 d . . . . .
H00B H 0.5669 0.0453 0.2783 0.074 Uiso 1 1 calc R U . . .
C00C C 0.5448(3) 0.0552(3) 0.40768(14) 0.0657(8) Uani 1 1 d . . . . .
H00C H 0.5183 0.0414 0.4490 0.079 Uiso 1 1 calc R U . . .
C00D C 0.9515(3) 0.2979(3) 0.58061(14) 0.0629(8) Uani 1 1 d . . . . .
C00E C 0.3572(3) -0.1075(3) 0.36320(15) 0.0697(8) Uani 1 1 d . . . . .
H00E H 0.3352 -0.1119 0.4059 0.084 Uiso 1 1 calc R U . . .
C00F C 0.2807(3) -0.1878(3) 0.31243(15) 0.0699(8) Uani 1 1 d . . . . .
H00F H 0.2059 -0.2439 0.3207 0.084 Uiso 1 1 calc R U . . .
C00G C 1.0193(3) 0.3739(4) 0.63814(16) 0.0770(9) Uani 1 1 d . . . . .
C00H C 0.8999(3) 0.5838(3) 0.59172(17) 0.0722(9) Uani 1 1 d . . . . .
C00I C 0.9896(4) 0.5148(4) 0.64193(17) 0.0856(10) Uani 1 1 d . . . . .
H00I H 1.0321 0.5639 0.6799 0.103 Uiso 1 1 calc R U . . .
C00J C 0.7397(4) 0.5839(3) 0.48360(18) 0.0828(10) Uani 1 1 d . . . . .
H00J H 0.6930 0.5371 0.4457 0.099 Uiso 1 1 calc R U . . .
C00K C 0.9844(4) 0.1536(3) 0.57816(17) 0.0839(10) Uani 1 1 d . . . . .
H00K H 0.9437 0.1017 0.5408 0.101 Uiso 1 1 calc R U . . .
C00L C 0.8730(5) 0.7284(4) 0.5956(2) 0.1033(13) Uani 1 1 d . . . . .
H00L H 0.9166 0.7781 0.6332 0.124 Uiso 1 1 calc R U . . .
C00M C 0.7182(4) 0.7212(4) 0.4891(2) 0.1111(14) Uani 1 1 d . . . . .
H00M H 0.6580 0.7684 0.4550 0.133 Uiso 1 1 calc R U . . .
C00N C 1.1132(4) 0.3024(6) 0.6903(2) 0.1176(15) Uani 1 1 d . . . . .
H00N H 1.1580 0.3508 0.7281 0.141 Uiso 1 1 calc R U . . .
C00O C 0.5603(4) -0.0264(5) 0.15542(18) 0.1200(15) Uani 1 1 d . . . . .
H00A H 0.5499 0.0708 0.1637 0.180 Uiso 1 1 calc R U . . .
H00D H 0.5619 -0.0406 0.1088 0.180 Uiso 1 1 calc R U . . .
H00G H 0.6486 -0.0596 0.1819 0.180 Uiso 1 1 calc R U . . .
C00P C 1.0728(5) 0.0920(4) 0.6287(3) 0.1152(14) Uani 1 1 d . . . . .
H00P H 1.0916 -0.0023 0.6260 0.138 Uiso 1 1 calc R U . . .
C00Q C 0.7866(5) 0.7932(4) 0.5464(3) 0.1222(16) Uani 1 1 d . . . . .
H00Q H 0.7709 0.8880 0.5498 0.147 Uiso 1 1 calc R U . . .
C00R C 1.1374(5) 0.1657(7) 0.6854(3) 0.142(2) Uani 1 1 d . . . . .
H00R H 1.1977 0.1200 0.7200 0.170 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
O001 C007 1.355(3) . ?
O001 H001 0.8200 . ?
O002 C005 1.367(3) . ?
O002 C00O 1.397(4) . ?
N5 C00C 1.270(3) . ?
N5 N004 1.414(3) . ?
N004 C009 1.235(3) . ?
C005 C00B 1.363(4) . ?
C005 C007 1.390(4) . ?
C006 C00D 1.394(4) . ?
C006 C00A 1.401(3) . ?
C006 C009 1.469(4) . ?
C007 C00F 1.368(4) . ?
C008 C00E 1.371(4) . ?
C008 C00B 1.391(4) . ?
C008 C00C 1.449(4) . ?
C009 H009 0.9300 . ?
C00A C00J 1.415(4) . ?
C00A C00H 1.419(4) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00D C00G 1.427(4) . ?
C00D C00K 1.428(4) . ?
C00E C00F 1.382(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G C00I 1.392(5) . ?
C00G C00N 1.427(5) . ?
C00H C00I 1.371(4) . ?
C00H C00L 1.422(4) . ?
C00I H00I 0.9300 . ?
C00J C00M 1.347(4) . ?
C00J H00J 0.9300 . ?
C00K C00P 1.337(5) . ?
C00K H00K 0.9300 . ?
C00L C00Q 1.324(5) . ?
C00L H00L 0.9300 . ?
C00M C00Q 1.405(5) . ?
C00M H00M 0.9300 . ?
C00N C00R 1.344(6) . ?
C00N H00N 0.9300 . ?
C00O H00A 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00G 0.9600 . ?
C00P C00R 1.393(6) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00R H00R 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
C007 O001 H001 109.5 . . ?
C005 O002 C00O 119.7(2) . . ?
C00C N5 N004 112.0(2) . . ?
C009 N004 N5 114.4(2) . . ?
C00B C005 O002 125.5(3) . . ?
C00B C005 C007 120.1(3) . . ?
O002 C005 C007 114.4(2) . . ?
C00D C006 C00A 121.0(3) . . ?
C00D C006 C009 121.3(2) . . ?
C00A C006 C009 117.7(2) . . ?
O001 C007 C00F 118.0(3) . . ?
O001 C007 C005 122.2(3) . . ?
C00F C007 C005 119.7(2) . . ?
C00E C008 C00B 119.0(3) . . ?
C00E C008 C00C 117.7(3) . . ?
C00B C008 C00C 123.3(3) . . ?
N004 C009 C006 123.9(3) . . ?
N004 C009 H009 118.1 . . ?
C006 C009 H009 118.1 . . ?
C006 C00A C00J 122.9(3) . . ?
C006 C00A C00H 119.4(3) . . ?
C00J C00A C00H 117.7(3) . . ?
C005 C00B C008 120.4(3) . . ?
C005 C00B H00B 119.8 . . ?
C008 C00B H00B 119.8 . . ?
N5 C00C C008 126.3(3) . . ?
N5 C00C H00C 116.9 . . ?
C008 C00C H00C 116.9 . . ?
C006 C00D C00G 119.2(3) . . ?
C006 C00D C00K 123.4(3) . . ?
C00G C00D C00K 117.5(3) . . ?
C008 C00E C00F 120.8(3) . . ?
C008 C00E H00E 119.6 . . ?
C00F C00E H00E 119.6 . . ?
C007 C00F C00E 119.9(3) . . ?
C007 C00F H00F 120.1 . . ?
C00E C00F H00F 120.1 . . ?
C00I C00G C00D 118.8(3) . . ?
C00I C00G C00N 122.3(4) . . ?
C00D C00G C00N 118.9(4) . . ?
C00I C00H C00A 119.3(3) . . ?
C00I C00H C00L 121.7(4) . . ?
C00A C00H C00L 118.9(4) . . ?
C00H C00I C00G 122.4(3) . . ?
C00H C00I H00I 118.8 . . ?
C00G C00I H00I 118.8 . . ?
C00M C00J C00A 121.4(3) . . ?
C00M C00J H00J 119.3 . . ?
C00A C00J H00J 119.3 . . ?
C00P C00K C00D 121.0(4) . . ?
C00P C00K H00K 119.5 . . ?
C00D C00K H00K 119.5 . . ?
C00Q C00L C00H 120.8(4) . . ?
C00Q C00L H00L 119.6 . . ?
C00H C00L H00L 119.6 . . ?
C00J C00M C00Q 120.0(4) . . ?
C00J C00M H00M 120.0 . . ?
C00Q C00M H00M 120.0 . . ?
C00R C00N C00G 120.6(4) . . ?
C00R C00N H00N 119.7 . . ?
C00G C00N H00N 119.7 . . ?
O002 C00O H00A 109.5 . . ?
O002 C00O H00D 109.5 . . ?
H00A C00O H00D 109.5 . . ?
O002 C00O H00G 109.5 . . ?
H00A C00O H00G 109.5 . . ?
H00D C00O H00G 109.5 . . ?
C00K C00P C00R 121.6(4) . . ?
C00K C00P H00P 119.2 . . ?
C00R C00P H00P 119.2 . . ?
C00L C00Q C00M 121.1(4) . . ?
C00L C00Q H00Q 119.4 . . ?
C00M C00Q H00Q 119.4 . . ?
C00N C00R C00P 120.5(4) . . ?
C00N C00R H00R 119.8 . . ?
C00P C00R H00R 119.8 . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036

