# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_NO_01_71_P
_database_code_depnum_ccdc_archive 'CCDC 2265977'
loop_
_audit_author_name
_audit_author_address
'Tapasi Chand'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2024-01-15 downloaded from the CCDC.
;
_audit_creation_date             2023-05-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         '0.2(C13 H9 N O3)'
_chemical_formula_sum            'C2.6 H1.8 N0.2 O0.6'
_chemical_formula_weight         45.444
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   3.8378(2)
_cell_length_b                   8.6367(5)
_cell_length_c                   29.4303(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     975.49(10)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    9536
_cell_measurement_temperature    185.00
_cell_measurement_theta_max      74.58
_cell_measurement_theta_min      3.96
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       irregular
_exptl_crystal_F_000             473.758
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.32
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.9731
_diffrn_reflns_Laue_measured_fraction_max 0.9731
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            4526
_diffrn_reflns_point_group_measured_fraction_full 0.9596
_diffrn_reflns_point_group_measured_fraction_max 0.9596
_diffrn_reflns_theta_full        66.5754
_diffrn_reflns_theta_max         66.58
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      185.00
_diffrn_measured_fraction_theta_full 0.9731
_diffrn_measured_fraction_theta_max 0.9731
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_reflns_Friedel_coverage         0.937
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              34
_reflns_limit_l_min              -34
_reflns_number_gt                1509
_reflns_number_total             1661
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.3834
_refine_diff_density_min         -0.2474
_refine_diff_density_rms         0.0676
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_d_res_high            0.8401
_refine_ls_d_res_low             14.7151
_refine_ls_extinction_coef       0.055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0463
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.0463
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+0.1125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1390
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00B), C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00H(H00a,H00c,H00d)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
O001 O 0.1575(5) 0.3479(2) 0.26851(5) 0.0415(5) Uani 1.000000 .
O002 O 0.6935(6) 0.0905(2) 0.38320(6) 0.0473(6) Uani 1.000000 .
O003 O 0.0087(6) 0.8501(2) 0.42627(6) 0.0480(6) Uani 1.000000 .
H003 H -0.057(11) 0.9284(15) 0.41171(14) 0.0720(8) Uiso 1.000000 GR
N004 N 0.4320(6) 0.2209(2) 0.32607(7) 0.0336(5) Uani 1.000000 .
C005 C 0.3007(6) 0.4723(3) 0.38476(8) 0.0300(5) Uani 1.000000 .
C006 C 0.4654(6) 0.3379(3) 0.40167(8) 0.0308(5) Uani 1.000000 .
C007 C 0.5686(7) 0.3302(3) 0.44661(8) 0.0351(6) Uani 1.000000 .
H007 H 0.6784(7) 0.2392(3) 0.45775(8) 0.0421(7) Uiso 1.000000 R
C008 C 0.2378(6) 0.5991(3) 0.41459(7) 0.0306(5) Uani 1.000000 .
C009 C -0.0263(7) 0.7396(3) 0.35172(8) 0.0350(6) Uani 1.000000 .
H009 H -0.1364(7) 0.8300(3) 0.34020(8) 0.0420(7) Uiso 1.000000 R
C00A C 0.1938(6) 0.4810(3) 0.33876(7) 0.0294(5) Uani 1.000000 .
C00B C 0.0374(7) 0.6145(3) 0.32311(8) 0.0336(6) Uani 1.000000 .
H00B H -0.0284(7) 0.6212(3) 0.29206(8) 0.0403(7) Uiso 1.000000 R
C00C C 0.2540(6) 0.3502(3) 0.30802(8) 0.0326(6) Uani 1.000000 .
C00D C 0.5371(7) 0.2078(3) 0.37068(8) 0.0346(6) Uani 1.000000 .
C00E C 0.3507(7) 0.5870(3) 0.46038(8) 0.0348(6) Uani 1.000000 .
H00E H 0.3139(7) 0.6712(3) 0.48061(8) 0.0418(7) Uiso 1.000000 R
C00F C 0.5119(7) 0.4557(3) 0.47578(7) 0.0367(6) Uani 1.000000 .
H00F H 0.5860(7) 0.4497(3) 0.50653(7) 0.0440(7) Uiso 1.000000 R
C00G C 0.0711(7) 0.7324(3) 0.39699(8) 0.0332(6) Uani 1.000000 .
C00H C 0.5122(8) 0.0928(3) 0.29522(9) 0.0437(7) Uani 1.000000 .
H00a H 0.364(4) 0.0039(9) 0.3025(5) 0.0656(10) Uiso 1.000000 GR
H00c H 0.469(5) 0.1252(9) 0.26381(10) 0.0656(10) Uiso 1.000000 GR
H00d H 0.7574(17) 0.0634(16) 0.2987(5) 0.0656(10) Uiso 1.000000 GR


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 C00C 1.220(3) . ?
O002 C00D 1.234(3) . ?
O003 H003 0.8400 . ?
O003 C00G 1.354(3) . ?
N004 C00C 1.412(3) . ?
N004 C00D 1.378(3) . ?
N004 C00H 1.464(3) . ?
C005 C006 1.412(3) . ?
C005 C008 1.424(3) . ?
C005 C00A 1.417(3) . ?
C006 C007 1.382(3) . ?
C006 C00D 1.473(3) . ?
C007 H007 0.9500 . ?
C007 C00F 1.400(3) . ?
C008 C00E 1.419(3) . ?
C008 C00G 1.415(3) . ?
C009 H009 0.9500 . ?
C009 C00B 1.392(3) . ?
C009 C00G 1.385(3) . ?
C00A C00B 1.379(3) . ?
C00A C00C 1.466(3) . ?
C00B H00B 0.9500 . ?
C00E H00E 0.9500 . ?
C00E C00F 1.369(4) . ?
C00F H00F 0.9500 . ?
C00H H00a 0.9800 . ?
C00H H00c 0.9800 . ?
C00H H00d 0.9800 . ?

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
C00G O003 H003 109.5 . . ?
C00D N004 C00C 124.4(2) . . ?
C00H N004 C00C 117.8(2) . . ?
C00H N004 C00D 117.8(2) . . ?
C008 C005 C006 119.4(2) . . ?
C00A C005 C006 120.7(2) . . ?
C00A C005 C008 119.9(2) . . ?
C007 C006 C005 120.4(2) . . ?
C00D C006 C005 119.5(2) . . ?
C00D C006 C007 120.1(2) . . ?
H007 C007 C006 119.84(14) . . ?
C00F C007 C006 120.3(2) . . ?
C00F C007 H007 119.84(14) . . ?
C00E C008 C005 118.5(2) . . ?
C00G C008 C005 118.5(2) . . ?
C00G C008 C00E 123.1(2) . . ?
C00B C009 H009 120.03(13) . . ?
C00G C009 H009 120.03(14) . . ?
C00G C009 C00B 119.9(2) . . ?
C00B C00A C005 119.3(2) . . ?
C00C C00A C005 120.2(2) . . ?
C00C C00A C00B 120.5(2) . . ?
C00A C00B C009 121.6(2) . . ?
H00B C00B C009 119.21(13) . . ?
H00B C00B C00A 119.21(13) . . ?
N004 C00C O001 119.5(2) . . ?
C00A C00C O001 123.5(2) . . ?
C00A C00C N004 117.0(2) . . ?
N004 C00D O002 119.6(2) . . ?
C006 C00D O002 122.2(2) . . ?
C006 C00D N004 118.2(2) . . ?
H00E C00E C008 119.56(15) . . ?
C00F C00E C008 120.9(2) . . ?
C00F C00E H00E 119.56(14) . . ?
C00E C00F C007 120.6(2) . . ?
H00F C00F C007 119.71(14) . . ?
H00F C00F C00E 119.71(14) . . ?
C008 C00G O003 117.2(2) . . ?
C009 C00G O003 122.0(2) . . ?
C009 C00G C008 120.7(2) . . ?
H00a C00H N004 109.5 . . ?
H00c C00H N004 109.5 . . ?
H00c C00H H00a 109.5 . . ?
H00d C00H N004 109.5 . . ?
H00d C00H H00a 109.5 . . ?
H00d C00H H00c 109.5 . . ?

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
O001 C00C N004 C00D -176.6(2) . . . . ?
O001 C00C N004 C00H 3.8(3) . . . . ?
O001 C00C C00A C005 177.3(2) . . . . ?
O001 C00C C00A C00B -3.7(3) . . . . ?
O002 C00D N004 C00C -179.5(2) . . . . ?
O002 C00D N004 C00H 0.1(3) . . . . ?
O002 C00D C006 C005 176.9(2) . . . . ?
O002 C00D C006 C007 -1.2(3) . . . . ?
O003 C00G C008 C005 178.8(2) . . . . ?
O003 C00G C008 C00E -2.3(3) . . . . ?
O003 C00G C009 C00B -178.8(2) . . . . ?
N004 C00C C00A C005 -2.3(2) . . . . ?
N004 C00C C00A C00B 176.7(2) . . . . ?
N004 C00D C006 C005 -1.5(3) . . . . ?
N004 C00D C006 C007 -179.5(2) . . . . ?
C005 C006 C007 C00F -0.3(3) . . . . ?
C005 C008 C00E C00F -0.9(3) . . . . ?
C005 C008 C00G C009 -0.5(3) . . . . ?
C005 C00A C00B C009 -1.7(3) . . . . ?
C006 C007 C00F C00E 0.7(3) . . . . ?
C007 C00F C00E C008 -0.1(3) . . . . ?
C008 C00G C009 C00B 0.5(3) . . . . ?
C009 C00B C00A C00C 179.3(2) . . . . ?


_olex2_submission_original_sample_id NO-01-71-P
_olex2_submission_special_instructions 'No special instructions were received'
