# Electronic Supplementary Material (ESI) for Green 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_200331BJHF_0m
_database_code_depnum_ccdc_archive 'CCDC 2054405'
loop_
_audit_author_name
_audit_author_address
'Naeem Iqbal'
;ChungAng University
South Korea
;
_audit_update_record             
;
2021-01-07 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.60(2)
_cell_length_b                   14.98(5)
_cell_length_c                   9.85(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.15(4)
_cell_angle_gamma                90
_cell_volume                     798(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3464
_diffrn_reflns_av_unetI/netI     0.1107
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.611
_diffrn_reflns_theta_max         28.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.710
_diffrn_reflns_point_group_measured_fraction_full 0.779
_reflns_number_total             2845
_reflns_number_gt                1399
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.536
_reflns_Friedel_fraction_max     0.515
_reflns_Friedel_fraction_full    0.605

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1023P)²+1.1479P] 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_abs_structure_details 
;
 Flack x determined using 455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2845
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1539
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2623
_refine_ls_wR_factor_gt          0.2264
_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
O001 O 0.8999(14) 0.4210(5) 0.7782(7) 0.076(2) Uani 1 1 d . . . . .
N002 N 0.8027(14) 0.4302(5) 0.5359(8) 0.0491(19) Uani 1 1 d . . . . .
C00A C 0.1365(17) 0.5558(7) 0.0547(9) 0.055(3) Uani 1 1 d . . . . .
H00A H 0.052376 0.504115 0.017535 0.066 Uiso 1 1 calc R U . . .
C00B C 0.3811(16) 0.5505(7) 0.1314(8) 0.048(2) Uani 1 1 d . . . . .
C00C C 0.6264(16) 0.4704(7) 0.4258(9) 0.049(2) Uani 1 1 d . . . . .
C00D C 0.155(2) 0.6130(8) 0.5407(12) 0.067(3) Uani 1 1 d . . . . .
H00D H 0.015534 0.648250 0.507875 0.080 Uiso 1 1 calc R U . . .
C00E C 0.5014(17) 0.6285(7) 0.1828(9) 0.054(2) Uani 1 1 d . . . . .
H00E H 0.666149 0.626914 0.234167 0.065 Uiso 1 1 calc R U . . .
C00F C 0.454(2) 0.5503(8) 0.7338(10) 0.066(3) Uani 1 1 d . . . . .
H00F H 0.518300 0.541975 0.829999 0.079 Uiso 1 1 calc R U . . .
C00G C 0.0161(19) 0.6370(9) 0.0329(10) 0.067(3) Uani 1 1 d . . . . .
H00G H -0.148547 0.639450 -0.018580 0.080 Uiso 1 1 calc R U . . .
C00H C 0.5067(16) 0.4627(7) 0.1592(9) 0.051(2) Uani 1 1 d . . . . .
C00I C 1.0103(18) 0.3402(8) 0.2557(12) 0.064(3) Uani 1 1 d . . . . .
H00I H 0.962433 0.343262 0.158043 0.076 Uiso 1 1 calc R U . . .
C00J C 0.378(2) 0.7093(8) 0.1581(11) 0.069(3) Uani 1 1 d . . . . .
H00J H 0.462023 0.761657 0.191748 0.083 Uiso 1 1 calc R U . . .
C00K C 1.163(2) 0.3294(7) 0.5489(13) 0.067(3) Uani 1 1 d . . . . .
H00K H 1.213697 0.326820 0.646602 0.080 Uiso 1 1 calc R U . . .
C00L C 1.289(2) 0.2853(8) 0.4693(15) 0.077(3) Uani 1 1 d . . . . .
H00L H 1.426105 0.250852 0.512650 0.093 Uiso 1 1 calc R U . . .
C00M C 1.216(2) 0.2911(8) 0.3238(15) 0.076(3) Uani 1 1 d . . . . .
H00M H 1.306837 0.261468 0.271011 0.092 Uiso 1 1 calc R U . . .
C00N C 0.471(2) 0.4007(8) 0.0581(10) 0.072(3) Uani 1 1 d . . . . .
H00B H 0.544424 0.344895 0.077277 0.086 Uiso 1 1 calc R U . . .
H00C H 0.371659 0.413424 -0.031370 0.086 Uiso 1 1 calc R U . . .
C00O C 0.136(2) 0.7137(7) 0.0857(10) 0.067(3) Uani 1 1 d . . . . .
H00O H 0.052896 0.768095 0.072400 0.080 Uiso 1 1 calc R U . . .
C00P C 0.249(2) 0.6029(8) 0.6828(12) 0.074(4) Uani 1 1 d . . . . .
H00P H 0.173709 0.631456 0.744624 0.089 Uiso 1 1 calc R U . . .
C003 C 0.7742(19) 0.4502(7) 0.6690(10) 0.056(3) Uani 1 1 d . . . . .
C004 C 0.2617(17) 0.5727(6) 0.4438(10) 0.052(2) Uani 1 1 d . . . . .
H004 H 0.194107 0.580037 0.347629 0.063 Uiso 1 1 calc R U . . .
C005 C 0.8761(17) 0.3847(6) 0.3351(10) 0.051(2) Uani 1 1 d . . . . .
C006 C 0.6625(15) 0.4429(6) 0.3002(9) 0.047(2) Uani 1 1 d . . . . .
C007 C 0.4698(16) 0.5217(6) 0.4943(9) 0.045(2) Uani 1 1 d . . . . .
C008 C 0.9600(18) 0.3779(7) 0.4812(10) 0.053(2) Uani 1 1 d . . . . .
C009 C 0.5619(19) 0.5107(6) 0.6394(9) 0.052(2) Uani 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
O001 C003 1.203(11) . ?
N002 C008 1.389(13) . ?
N002 C003 1.394(13) . ?
N002 C00C 1.398(11) . ?
C00A C00G 1.381(15) . ?
C00A C00B 1.383(12) . ?
C00A H00A 0.9300 . ?
C00B C00E 1.378(13) . ?
C00B C00H 1.483(14) . ?
C00C C006 1.369(13) . ?
C00C C007 1.457(13) . ?
C00D C00P 1.368(15) . ?
C00D C004 1.389(13) . ?
C00D H00D 0.9300 . ?
C00E C00J 1.384(15) . ?
C00E H00E 0.9300 . ?
C00F C009 1.369(14) . ?
C00F C00P 1.377(17) . ?
C00F H00F 0.9300 . ?
C00G C00O 1.362(15) . ?
C00G H00G 0.9300 . ?
C00H C00N 1.338(13) . ?
C00H C006 1.465(13) . ?
C00I C00M 1.383(16) . ?
C00I C005 1.389(14) . ?
C00I H00I 0.9300 . ?
C00J C00O 1.359(15) . ?
C00J H00J 0.9300 . ?
C00K C00L 1.356(17) . ?
C00K C008 1.368(14) . ?
C00K H00K 0.9300 . ?
C00L C00M 1.387(19) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00B 0.9300 . ?
C00N H00C 0.9300 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C003 C009 1.462(15) . ?
C004 C007 1.374(13) . ?
C004 H004 0.9300 . ?
C005 C008 1.396(14) . ?
C005 C006 1.448(13) . ?
C007 C009 1.398(14) . ?

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
C008 N002 C003 136.6(8) . . ?
C008 N002 C00C 109.5(8) . . ?
C003 N002 C00C 113.9(8) . . ?
C00G C00A C00B 120.6(9) . . ?
C00G C00A H00A 119.7 . . ?
C00B C00A H00A 119.7 . . ?
C00E C00B C00A 118.1(9) . . ?
C00E C00B C00H 121.5(9) . . ?
C00A C00B C00H 120.4(8) . . ?
C006 C00C N002 109.3(8) . . ?
C006 C00C C007 145.7(9) . . ?
N002 C00C C007 104.9(7) . . ?
C00P C00D C004 122.5(11) . . ?
C00P C00D H00D 118.7 . . ?
C004 C00D H00D 118.7 . . ?
C00B C00E C00J 120.2(9) . . ?
C00B C00E H00E 119.9 . . ?
C00J C00E H00E 119.9 . . ?
C009 C00F C00P 118.4(10) . . ?
C009 C00F H00F 120.8 . . ?
C00P C00F H00F 120.8 . . ?
C00O C00G C00A 120.8(10) . . ?
C00O C00G H00G 119.6 . . ?
C00A C00G H00G 119.6 . . ?
C00N C00H C006 120.1(10) . . ?
C00N C00H C00B 120.4(9) . . ?
C006 C00H C00B 119.4(8) . . ?
C00M C00I C005 119.1(11) . . ?
C00M C00I H00I 120.4 . . ?
C005 C00I H00I 120.4 . . ?
C00O C00J C00E 121.2(10) . . ?
C00O C00J H00J 119.4 . . ?
C00E C00J H00J 119.4 . . ?
C00L C00K C008 118.0(11) . . ?
C00L C00K H00K 121.0 . . ?
C008 C00K H00K 121.0 . . ?
C00K C00L C00M 120.6(11) . . ?
C00K C00L H00L 119.7 . . ?
C00M C00L H00L 119.7 . . ?
C00I C00M C00L 121.2(11) . . ?
C00I C00M H00M 119.4 . . ?
C00L C00M H00M 119.4 . . ?
C00H C00N H00B 120.0 . . ?
C00H C00N H00C 120.0 . . ?
H00B C00N H00C 120.0 . . ?
C00J C00O C00G 118.9(11) . . ?
C00J C00O H00O 120.5 . . ?
C00G C00O H00O 120.5 . . ?
C00D C00P C00F 119.8(10) . . ?
C00D C00P H00P 120.1 . . ?
C00F C00P H00P 120.1 . . ?
O001 C003 N002 125.3(11) . . ?
O001 C003 C009 131.2(9) . . ?
N002 C003 C009 103.5(8) . . ?
C007 C004 C00D 117.9(10) . . ?
C007 C004 H004 121.0 . . ?
C00D C004 H004 121.0 . . ?
C00I C005 C008 117.4(9) . . ?
C00I C005 C006 133.7(9) . . ?
C008 C005 C006 108.9(8) . . ?
C00C C006 C005 105.9(8) . . ?
C00C C006 C00H 127.2(9) . . ?
C005 C006 C00H 126.8(8) . . ?
C004 C007 C009 119.2(9) . . ?
C004 C007 C00C 133.0(9) . . ?
C009 C007 C00C 107.7(8) . . ?
C00K C008 N002 129.9(10) . . ?
C00K C008 C005 123.7(10) . . ?
N002 C008 C005 106.4(8) . . ?
C00F C009 C007 122.2(10) . . ?
C00F C009 C003 127.8(9) . . ?
C007 C009 C003 109.9(8) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039

