# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_ans4
_database_code_depnum_ccdc_archive 'CCDC 2414088'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;IACS, Kolkata
India
;
_audit_update_record             
;
2025-01-02 deposited with the CCDC.	2025-07-17 downloaded from the CCDC.
;
_audit_creation_date             2024-06-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O3'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.2794(11)
_cell_length_b                   4.2726(3)
_cell_length_c                   22.8872(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.816(3)
_cell_angle_gamma                90
_cell_volume                     1371.55(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4910
_cell_measurement_temperature    298.33
_cell_measurement_theta_max      27.915
_cell_measurement_theta_min      2.526
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1686 before and 0.0930 after correction.
The Ratio of minimum to maximum transmission is 0.8070.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_preparation       
'SLOW EVAPORATION OF ISOPROPANOL AND CHOLOROFORM MIXTURE'
_exptl_crystal_recrystallization_method 'SLOW EVAPORATION'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11523
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.957
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_temperature      298.33
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2185
_reflns_number_total             3265
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0473P)²+0.3247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1298
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C16(H16), C5(H5), C15(H15), C14(H14), C6(H6)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.80341(8) 0.7107(3) 0.36637(5) 0.0477(3) Uani 1 1 d . . . . .
O1 O 0.93249(8) 0.7324(3) 0.55825(6) 0.0550(4) Uani 1 1 d . . . . .
N1 N 0.80295(8) 0.8401(3) 0.48611(6) 0.0362(3) Uani 1 1 d . . . . .
O3 O 0.78225(10) 0.0542(3) 0.70399(6) 0.0601(4) Uani 1 1 d . . . . .
N2 N 0.64741(9) 0.6587(3) 0.49017(6) 0.0399(3) Uani 1 1 d . . . . .
C4 C 0.68465(11) 0.5207(4) 0.54437(7) 0.0378(4) Uani 1 1 d . . . . .
C9 C 0.67069(11) 0.9361(4) 0.40312(7) 0.0387(4) Uani 1 1 d . . . . .
C3 C 0.78181(10) 0.5286(4) 0.56940(7) 0.0371(4) Uani 1 1 d . . . . .
C8 C 0.70633(10) 0.8031(4) 0.46294(7) 0.0364(4) Uani 1 1 d . . . . .
C13 C 0.58561(11) 1.1013(4) 0.39164(8) 0.0452(4) Uani 1 1 d . . . . .
H13 H 0.551306 1.131788 0.421926 0.054 Uiso 1 1 calc R U . . .
C12 C 0.86058(11) 1.0368(4) 0.45362(7) 0.0417(4) Uani 1 1 d . . . . .
H12A H 0.918913 1.097251 0.480221 0.050 Uiso 1 1 calc R U . . .
H12B H 0.825478 1.225929 0.440214 0.050 Uiso 1 1 calc R U . . .
C7 C 0.84652(11) 0.7032(4) 0.53929(7) 0.0390(4) Uani 1 1 d . . . . .
C10 C 0.72036(11) 0.8873(4) 0.35655(8) 0.0412(4) Uani 1 1 d . . . . .
C2 C 0.81805(12) 0.3747(4) 0.62301(7) 0.0422(4) Uani 1 1 d . . . . .
H2 H 0.882896 0.380670 0.639007 0.051 Uiso 1 1 calc R U . . .
C16 C 0.68490(13) 1.0005(4) 0.30031(8) 0.0499(4) Uani 1 1 d . . . . .
H16 H 0.717495 0.963632 0.269417 0.060 Uiso 1 1 calc R U . . .
C5 C 0.62316(12) 0.3567(4) 0.57476(8) 0.0473(4) Uani 1 1 d . . . . .
H5 H 0.558166 0.349082 0.559229 0.057 Uiso 1 1 calc R U . . .
C11 C 0.88505(12) 0.8671(4) 0.40077(8) 0.0474(4) Uani 1 1 d . . . . .
H11A H 0.910049 1.015811 0.375579 0.057 Uiso 1 1 calc R U . . .
H11B H 0.934475 0.714085 0.414489 0.057 Uiso 1 1 calc R U . . .
C1 C 0.75621(13) 0.2152(4) 0.65148(8) 0.0459(4) Uani 1 1 d . . . . .
C15 C 0.60077(14) 1.1689(5) 0.29003(9) 0.0555(5) Uani 1 1 d . . . . .
H15 H 0.577315 1.247459 0.252223 0.067 Uiso 1 1 calc R U . . .
C14 C 0.55123(12) 1.2215(4) 0.33550(9) 0.0529(5) Uani 1 1 d . . . . .
H14 H 0.495042 1.337035 0.328434 0.063 Uiso 1 1 calc R U . . .
C6 C 0.65879(13) 0.2084(5) 0.62712(8) 0.0510(5) Uani 1 1 d . . . . .
H6 H 0.617471 0.100930 0.646928 0.061 Uiso 1 1 calc R U . . .
C17 C 0.87846(16) 0.0655(7) 0.73228(10) 0.0790(7) Uani 1 1 d . . . . .
H17A H 0.917316 -0.027305 0.706961 0.118 Uiso 1 1 calc R U . . .
H17B H 0.886559 -0.047861 0.769099 0.118 Uiso 1 1 calc R U . . .
H17C H 0.897234 0.279485 0.740108 0.118 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
O2 C10 1.3880(19) . ?
O2 C11 1.443(2) . ?
O1 C7 1.2293(17) . ?
N1 C8 1.3910(18) . ?
N1 C12 1.4716(19) . ?
N1 C7 1.388(2) . ?
O3 C1 1.374(2) . ?
O3 C17 1.406(2) . ?
N2 C4 1.387(2) . ?
N2 C8 1.294(2) . ?
C4 C3 1.398(2) . ?
C4 C5 1.405(2) . ?
C9 C8 1.481(2) . ?
C9 C13 1.387(2) . ?
C9 C10 1.402(2) . ?
C3 C7 1.457(2) . ?
C3 C2 1.402(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.506(2) . ?
C10 C16 1.379(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.373(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C1 C6 1.398(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C10 O2 C11 114.51(13) . . ?
C8 N1 C12 118.74(13) . . ?
C7 N1 C8 122.39(13) . . ?
C7 N1 C12 118.86(12) . . ?
C1 O3 C17 117.80(15) . . ?
C8 N2 C4 117.33(13) . . ?
N2 C4 C3 122.73(14) . . ?
N2 C4 C5 118.99(14) . . ?
C3 C4 C5 118.25(15) . . ?
C13 C9 C8 120.47(15) . . ?
C13 C9 C10 118.79(16) . . ?
C10 C9 C8 120.69(14) . . ?
C4 C3 C7 119.14(14) . . ?
C4 C3 C2 121.45(15) . . ?
C2 C3 C7 119.41(14) . . ?
N1 C8 C9 116.93(13) . . ?
N2 C8 N1 123.97(15) . . ?
N2 C8 C9 119.10(14) . . ?
C9 C13 H13 119.7 . . ?
C14 C13 C9 120.65(17) . . ?
C14 C13 H13 119.7 . . ?
N1 C12 H12A 109.3 . . ?
N1 C12 H12B 109.3 . . ?
N1 C12 C11 111.53(13) . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
O1 C7 N1 121.35(15) . . ?
O1 C7 C3 124.39(15) . . ?
N1 C7 C3 114.26(13) . . ?
O2 C10 C9 119.77(15) . . ?
C16 C10 O2 119.63(15) . . ?
C16 C10 C9 120.52(16) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 118.90(16) . . ?
C1 C2 H2 120.5 . . ?
C10 C16 H16 120.1 . . ?
C10 C16 C15 119.77(18) . . ?
C15 C16 H16 120.1 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.05(16) . . ?
C6 C5 H5 120.0 . . ?
O2 C11 C12 112.07(13) . . ?
O2 C11 H11A 109.2 . . ?
O2 C11 H11B 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O3 C1 C6 115.08(16) . . ?
C2 C1 O3 124.83(17) . . ?
C2 C1 C6 120.09(17) . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.52(17) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.72(17) . . ?
C15 C14 H14 120.1 . . ?
C5 C6 C1 121.25(16) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 C10 C16 C15 178.17(16) . . . . ?
N1 C12 C11 O2 46.10(19) . . . . ?
O3 C1 C6 C5 -179.47(16) . . . . ?
N2 C4 C3 C7 3.5(2) . . . . ?
N2 C4 C3 C2 -177.07(14) . . . . ?
N2 C4 C5 C6 177.46(16) . . . . ?
C4 N2 C8 N1 -3.2(2) . . . . ?
C4 N2 C8 C9 176.04(13) . . . . ?
C4 C3 C7 O1 177.89(16) . . . . ?
C4 C3 C7 N1 -1.8(2) . . . . ?
C4 C3 C2 C1 -0.5(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C9 C13 C14 C15 1.8(3) . . . . ?
C9 C10 C16 C15 1.3(3) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C2 C1 O3 179.77(15) . . . . ?
C3 C2 C1 C6 -0.2(3) . . . . ?
C8 N1 C12 C11 -77.66(18) . . . . ?
C8 N1 C7 O1 178.17(15) . . . . ?
C8 N1 C7 C3 -2.1(2) . . . . ?
C8 N2 C4 C3 -1.0(2) . . . . ?
C8 N2 C4 C5 -178.83(15) . . . . ?
C8 C9 C13 C14 -178.90(15) . . . . ?
C8 C9 C10 O2 0.5(2) . . . . ?
C8 C9 C10 C16 177.32(15) . . . . ?
C13 C9 C8 N1 -136.30(15) . . . . ?
C13 C9 C8 N2 44.4(2) . . . . ?
C13 C9 C10 O2 -177.13(14) . . . . ?
C13 C9 C10 C16 -0.3(2) . . . . ?
C12 N1 C8 N2 -173.77(14) . . . . ?
C12 N1 C8 C9 6.9(2) . . . . ?
C12 N1 C7 O1 -3.1(2) . . . . ?
C12 N1 C7 C3 176.62(13) . . . . ?
C7 N1 C8 N2 5.0(2) . . . . ?
C7 N1 C8 C9 -174.31(13) . . . . ?
C7 N1 C12 C11 103.55(16) . . . . ?
C7 C3 C2 C1 178.95(15) . . . . ?
C10 O2 C11 C12 43.90(19) . . . . ?
C10 C9 C8 N1 46.1(2) . . . . ?
C10 C9 C8 N2 -133.21(16) . . . . ?
C10 C9 C13 C14 -1.3(2) . . . . ?
C10 C16 C15 C14 -0.8(3) . . . . ?
C2 C3 C7 O1 -1.5(2) . . . . ?
C2 C3 C7 N1 178.76(14) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C16 C15 C14 C13 -0.7(3) . . . . ?
C5 C4 C3 C7 -178.64(14) . . . . ?
C5 C4 C3 C2 0.8(2) . . . . ?
C11 O2 C10 C9 -74.01(18) . . . . ?
C11 O2 C10 C16 109.14(17) . . . . ?
C17 O3 C1 C2 3.3(3) . . . . ?
C17 O3 C1 C6 -176.81(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_jd281024_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2414089'
loop_
_audit_author_name
_audit_author_address
'Jyotirmayee Dash'
;IACS, Kolkata
India
;
_audit_update_record             
;
2025-01-02 deposited with the CCDC.	2025-07-17 downloaded from the CCDC.
;
_audit_creation_date             2024-12-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   15.052(3)
_cell_length_b                   22.635(5)
_cell_length_c                   4.2116(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1434.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2718
_cell_measurement_temperature    160.01
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1461 before and 0.1064 after correction.
The Ratio of minimum to maximum transmission is 0.7118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_preparation       'Slow evaporation of Isoprpanol'
_exptl_crystal_recrystallization_method 'Slow evaporation'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13575
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         2.251
_diffrn_ambient_temperature      160.01
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.569
_reflns_Friedel_fraction_full    0.777
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                1561
_reflns_number_total             2357
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.087
_refine_ls_abs_structure_details 
;
 Flack x determined using 469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0702
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1025P)²+0.6704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.2181
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C19(H19a,H19b)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C1(H1), C2(H2), C11(H11), C12(H12), C16(H16), C18(H18), C4(H4),
 C3(H3), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.5075(3) 0.6595(2) 0.3309(12) 0.0381(12) Uani 1 1 d . . . . .
O002 O 0.3818(3) 0.48996(19) 0.4453(15) 0.0449(13) Uani 1 1 d . . . . .
N003 N 0.3709(3) 0.5892(2) 0.5332(13) 0.0320(14) Uani 1 1 d . . . . .
N004 N 0.2482(3) 0.6457(2) 0.3550(15) 0.0354(14) Uani 1 1 d . . . . .
C005 C 0.3262(4) 0.6422(3) 0.4867(17) 0.0306(15) Uani 1 1 d . . . . .
C006 C 0.4621(4) 0.7041(3) 0.4887(19) 0.0331(15) Uani 1 1 d . . . . .
C007 C 0.2533(4) 0.5396(3) 0.2520(18) 0.0326(16) Uani 1 1 d . . . . .
C008 C 0.3388(4) 0.5359(3) 0.4126(17) 0.0331(16) Uani 1 1 d . . . . .
C009 C 0.2095(4) 0.5942(3) 0.2456(19) 0.0341(16) Uani 1 1 d . . . . .
C00A C 0.3300(4) 0.7469(3) 0.7181(17) 0.0323(15) Uani 1 1 d . . . . .
C00B C 0.3773(4) 0.8005(3) 0.7680(18) 0.0352(17) Uani 1 1 d . . . . .
C00C C 0.2402(4) 0.7453(3) 0.822(2) 0.0373(17) Uani 1 1 d . . . . .
H00C H 0.206561 0.710224 0.792906 0.045 Uiso 1 1 calc R U . . .
C00D C 0.3744(4) 0.6976(3) 0.5721(16) 0.0315(17) Uani 1 1 d . . . . .
C00E C 0.2135(4) 0.4898(3) 0.1192(18) 0.0389(18) Uani 1 1 d . . . . .
H00E H 0.243965 0.453020 0.121343 0.047 Uiso 1 1 calc R U . . .
C00F C 0.4534(4) 0.5888(3) 0.716(2) 0.0361(16) Uani 1 1 d . . . . .
H00A H 0.464539 0.548363 0.796816 0.043 Uiso 1 1 calc R U . . .
H00B H 0.447126 0.615389 0.901275 0.043 Uiso 1 1 calc R U . . .
C00G C 0.1307(4) 0.4936(3) -0.014(2) 0.0416(18) Uani 1 1 d . . . . .
H00G H 0.103860 0.459760 -0.106437 0.050 Uiso 1 1 calc R U . . .
C00H C 0.5084(4) 0.7573(3) 0.5298(19) 0.0363(17) Uani 1 1 d . . . . .
H00H H 0.568762 0.760567 0.465882 0.044 Uiso 1 1 calc R U . . .
C00I C 0.4661(4) 0.8041(3) 0.662(2) 0.0397(18) Uani 1 1 d . . . . .
H00I H 0.497173 0.840384 0.683119 0.048 Uiso 1 1 calc R U . . .
C00J C 0.2013(5) 0.7924(3) 0.963(2) 0.0429(18) Uani 1 1 d . . . . .
H00J H 0.140822 0.790022 1.026182 0.051 Uiso 1 1 calc R U . . .
C00K C 0.3355(5) 0.8484(3) 0.9142(19) 0.0412(19) Uani 1 1 d . . . . .
H00K H 0.367877 0.884024 0.943774 0.049 Uiso 1 1 calc R U . . .
C00L C 0.5312(4) 0.6083(3) 0.519(2) 0.0400(18) Uani 1 1 d . . . . .
H00D H 0.581665 0.618256 0.660266 0.048 Uiso 1 1 calc R U . . .
H00F H 0.549928 0.575708 0.377881 0.048 Uiso 1 1 calc R U . . .
C00M C 0.1242(4) 0.5969(3) 0.1111(19) 0.0412(19) Uani 1 1 d . . . . .
H00M H 0.092935 0.633336 0.107286 0.049 Uiso 1 1 calc R U . . .
C00N C 0.0863(4) 0.5475(3) -0.014(2) 0.0452(19) Uani 1 1 d . . . . .
H00N H 0.028367 0.549889 -0.102402 0.054 Uiso 1 1 calc R U . . .
C00O C 0.2494(5) 0.8454(3) 1.016(2) 0.047(2) Uani 1 1 d . . . . .
H00O H 0.222383 0.878042 1.120140 0.056 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 C006 1.390(8) . ?
O001 C00L 1.448(8) . ?
O002 C008 1.234(7) . ?
N003 C005 1.391(7) . ?
N003 C008 1.394(8) . ?
N003 C00F 1.462(8) . ?
N004 C005 1.302(8) . ?
N004 C009 1.382(8) . ?
C005 C00D 1.492(8) . ?
C006 C00D 1.374(8) . ?
C006 C00H 1.402(8) . ?
C007 C008 1.455(9) . ?
C007 C009 1.400(8) . ?
C007 C00E 1.394(9) . ?
C009 C00M 1.405(9) . ?
C00A C00B 1.423(8) . ?
C00A C00C 1.422(9) . ?
C00A C00D 1.439(9) . ?
C00B C00I 1.413(9) . ?
C00B C00K 1.396(9) . ?
C00C H00C 0.9500 . ?
C00C C00J 1.352(9) . ?
C00E H00E 0.9500 . ?
C00E C00G 1.370(10) . ?
C00F H00A 0.9900 . ?
C00F H00B 0.9900 . ?
C00F C00L 1.500(10) . ?
C00G H00G 0.9500 . ?
C00G C00N 1.391(9) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.353(9) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00O 1.419(10) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.368(9) . ?
C00L H00D 0.9900 . ?
C00L H00F 0.9900 . ?
C00M H00M 0.9500 . ?
C00M C00N 1.361(9) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?

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
C006 O001 C00L 116.1(6) . . ?
C005 N003 C008 121.9(5) . . ?
C005 N003 C00F 119.4(5) . . ?
C008 N003 C00F 118.8(5) . . ?
C005 N004 C009 118.1(5) . . ?
N003 C005 C00D 117.1(5) . . ?
N004 C005 N003 123.2(5) . . ?
N004 C005 C00D 119.5(5) . . ?
O001 C006 C00H 116.1(5) . . ?
C00D C006 O001 121.1(5) . . ?
C00D C006 C00H 122.6(6) . . ?
C009 C007 C008 118.4(6) . . ?
C00E C007 C008 121.3(6) . . ?
C00E C007 C009 120.2(6) . . ?
O002 C008 N003 120.4(6) . . ?
O002 C008 C007 124.3(6) . . ?
N003 C008 C007 115.3(5) . . ?
N004 C009 C007 122.7(5) . . ?
N004 C009 C00M 118.8(6) . . ?
C007 C009 C00M 118.5(6) . . ?
C00B C00A C00D 119.5(6) . . ?
C00C C00A C00B 116.8(6) . . ?
C00C C00A C00D 123.7(6) . . ?
C00I C00B C00A 118.4(6) . . ?
C00K C00B C00A 120.2(6) . . ?
C00K C00B C00I 121.4(6) . . ?
C00A C00C H00C 119.1 . . ?
C00J C00C C00A 121.8(6) . . ?
C00J C00C H00C 119.1 . . ?
C006 C00D C005 119.8(6) . . ?
C006 C00D C00A 118.2(5) . . ?
C00A C00D C005 121.9(5) . . ?
C007 C00E H00E 119.9 . . ?
C00G C00E C007 120.3(6) . . ?
C00G C00E H00E 119.9 . . ?
N003 C00F H00A 109.3 . . ?
N003 C00F H00B 109.3 . . ?
N003 C00F C00L 111.7(6) . . ?
H00A C00F H00B 107.9 . . ?
C00L C00F H00A 109.3 . . ?
C00L C00F H00B 109.3 . . ?
C00E C00G H00G 120.2 . . ?
C00E C00G C00N 119.5(7) . . ?
C00N C00G H00G 120.2 . . ?
C006 C00H H00H 120.4 . . ?
C00I C00H C006 119.2(6) . . ?
C00I C00H H00H 120.4 . . ?
C00B C00I H00I 119.0 . . ?
C00H C00I C00B 122.1(6) . . ?
C00H C00I H00I 119.0 . . ?
C00C C00J H00J 119.5 . . ?
C00C C00J C00O 121.0(7) . . ?
C00O C00J H00J 119.5 . . ?
C00B C00K H00K 119.1 . . ?
C00O C00K C00B 121.8(6) . . ?
C00O C00K H00K 119.1 . . ?
O001 C00L C00F 110.3(5) . . ?
O001 C00L H00D 109.6 . . ?
O001 C00L H00F 109.6 . . ?
C00F C00L H00D 109.6 . . ?
C00F C00L H00F 109.6 . . ?
H00D C00L H00F 108.1 . . ?
C009 C00M H00M 119.9 . . ?
C00N C00M C009 120.2(7) . . ?
C00N C00M H00M 119.9 . . ?
C00G C00N H00N 119.4 . . ?
C00M C00N C00G 121.3(7) . . ?
C00M C00N H00N 119.4 . . ?
C00J C00O H00O 120.8 . . ?
C00K C00O C00J 118.4(7) . . ?
C00K C00O H00O 120.8 . . ?

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 C006 C00D C005 -1.3(10) . . . . ?
O001 C006 C00D C00A -176.3(6) . . . . ?
O001 C006 C00H C00I 175.4(7) . . . . ?
N003 C005 C00D C006 43.4(9) . . . . ?
N003 C005 C00D C00A -141.8(7) . . . . ?
N003 C00F C00L O001 43.6(8) . . . . ?
N004 C005 C00D C006 -132.2(7) . . . . ?
N004 C005 C00D C00A 42.7(10) . . . . ?
N004 C009 C00M C00N 176.6(7) . . . . ?
C005 N003 C008 O002 176.7(6) . . . . ?
C005 N003 C008 C007 -3.4(9) . . . . ?
C005 N003 C00F C00L -80.3(7) . . . . ?
C005 N004 C009 C007 -4.4(10) . . . . ?
C005 N004 C009 C00M 178.2(7) . . . . ?
C006 O001 C00L C00F 46.0(8) . . . . ?
C006 C00H C00I C00B 1.9(11) . . . . ?
C007 C009 C00M C00N -1.0(11) . . . . ?
C007 C00E C00G C00N -0.6(12) . . . . ?
C008 N003 C005 N004 6.5(10) . . . . ?
C008 N003 C005 C00D -168.8(6) . . . . ?
C008 N003 C00F C00L 100.3(7) . . . . ?
C008 C007 C009 N004 7.1(11) . . . . ?
C008 C007 C009 C00M -175.4(7) . . . . ?
C008 C007 C00E C00G 176.1(7) . . . . ?
C009 N004 C005 N003 -2.5(10) . . . . ?
C009 N004 C005 C00D 172.7(6) . . . . ?
C009 C007 C008 O002 176.9(7) . . . . ?
C009 C007 C008 N003 -3.0(9) . . . . ?
C009 C007 C00E C00G -1.0(11) . . . . ?
C009 C00M C00N C00G -0.6(13) . . . . ?
C00A C00B C00I C00H -3.5(11) . . . . ?
C00A C00B C00K C00O 0.6(12) . . . . ?
C00A C00C C00J C00O -1.0(13) . . . . ?
C00B C00A C00C C00J 0.0(11) . . . . ?
C00B C00A C00D C005 -174.3(6) . . . . ?
C00B C00A C00D C006 0.7(10) . . . . ?
C00B C00K C00O C00J -1.7(12) . . . . ?
C00C C00A C00B C00I -178.7(7) . . . . ?
C00C C00A C00B C00K 0.2(10) . . . . ?
C00C C00A C00D C005 6.7(10) . . . . ?
C00C C00A C00D C006 -178.4(6) . . . . ?
C00C C00J C00O C00K 1.8(12) . . . . ?
C00D C006 C00H C00I 1.2(11) . . . . ?
C00D C00A C00B C00I 2.1(10) . . . . ?
C00D C00A C00B C00K -178.9(7) . . . . ?
C00D C00A C00C C00J 179.1(8) . . . . ?
C00E C007 C008 O002 -0.3(11) . . . . ?
C00E C007 C008 N003 179.8(6) . . . . ?
C00E C007 C009 N004 -175.7(7) . . . . ?
C00E C007 C009 C00M 1.7(11) . . . . ?
C00E C00G C00N C00M 1.4(13) . . . . ?
C00F N003 C005 N004 -172.9(7) . . . . ?
C00F N003 C005 C00D 11.8(9) . . . . ?
C00F N003 C008 O002 -3.9(10) . . . . ?
C00F N003 C008 C007 176.0(6) . . . . ?
C00H C006 C00D C005 172.7(7) . . . . ?
C00H C006 C00D C00A -2.4(11) . . . . ?
C00I C00B C00K C00O 179.6(7) . . . . ?
C00K C00B C00I C00H 177.6(8) . . . . ?
C00L O001 C006 C00D -73.6(8) . . . . ?
C00L O001 C006 C00H 112.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
