# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_KA1113_0m
_database_code_depnum_ccdc_archive 'CCDC 2104599'
loop_
_audit_author_name
_audit_author_address
'Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N O3'
_chemical_formula_sum            'C12 H9 N O3'
_chemical_formula_weight         215.20

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.0423(14)
_cell_length_b                   8.8382(13)
_cell_length_c                   17.048(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1061.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    3047
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.66

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6303
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10127
_diffrn_reflns_av_unetI/netI     0.0675
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         26.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2198
_reflns_number_gt                1613
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2198
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1375
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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
C1 C 0.4114(6) 0.3055(4) 0.3850(2) 0.0373(9) Uani 1 1 d . . . . .
C2 C 0.2282(6) 0.2605(4) 0.3672(2) 0.0378(9) Uani 1 1 d . . . . .
C3 C 0.1578(7) 0.1183(5) 0.3867(3) 0.0522(11) Uani 1 1 d . . . . .
H3 H 0.035185 0.088629 0.373493 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2809(9) 0.0231(5) 0.4270(3) 0.0628(15) Uani 1 1 d . . . . .
H4 H 0.239688 -0.073080 0.441079 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4625(9) 0.0673(5) 0.4466(3) 0.0636(15) Uani 1 1 d . . . . .
H5 H 0.540656 0.001118 0.474052 0.076 Uiso 1 1 calc R U . . .
C6 C 0.5302(7) 0.2091(5) 0.4260(2) 0.0528(12) Uani 1 1 d . . . . .
H6 H 0.652734 0.238682 0.439388 0.063 Uiso 1 1 calc R U . . .
C7 C 0.4408(5) 0.4644(4) 0.3531(2) 0.0333(9) Uani 1 1 d . . . . .
C8 C 0.2477(6) 0.4974(4) 0.3158(2) 0.0417(9) Uani 1 1 d . . . . .
C9 C 0.4742(6) 0.5868(4) 0.4172(3) 0.0433(10) Uani 1 1 d . . . . .
C10 C 0.6072(5) 0.4914(4) 0.2945(2) 0.0415(9) Uani 1 1 d . . . . .
H10 H 0.558144 0.512350 0.241807 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7085(6) 0.6275(4) 0.3267(3) 0.0472(10) Uani 1 1 d . . . . .
H11 H 0.811809 0.672658 0.302072 0.057 Uiso 1 1 calc R U . . .
C12 C 0.6363(7) 0.6764(4) 0.3935(3) 0.0504(11) Uani 1 1 d . . . . .
H12 H 0.683631 0.758167 0.421767 0.061 Uiso 1 1 calc R U . . .
O1 O 0.3754(6) 0.6016(4) 0.4747(2) 0.0752(11) Uani 1 1 d . . . . .
O2 O 0.2041(4) 0.6147(3) 0.2815(2) 0.0679(10) Uani 1 1 d . . . . .
O3 O 0.7426(4) 0.3738(3) 0.2921(2) 0.0574(9) Uani 1 1 d . . . . .
H3O H 0.701(9) 0.306(7) 0.253(4) 0.12(2) Uiso 1 1 d . . . . .
N1 N 0.1334(5) 0.3772(4) 0.3269(2) 0.0448(9) Uani 1 1 d . . . . .
H1N H 0.015(6) 0.372(5) 0.311(2) 0.048(12) Uiso 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
C1 C6 1.384(5) . ?
C1 C2 1.384(6) . ?
C1 C7 1.520(5) . ?
C2 C3 1.392(5) . ?
C2 N1 1.408(5) . ?
C3 C4 1.390(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.528(5) . ?
C7 C9 1.556(5) . ?
C7 C10 1.558(5) . ?
C8 O2 1.230(4) . ?
C8 N1 1.346(5) . ?
C9 O1 1.209(5) . ?
C9 C12 1.447(6) . ?
C10 O3 1.411(5) . ?
C10 C11 1.502(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.320(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
O3 H3O 0.94(7) . ?
N1 H1N 0.88(4) . ?

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
C6 C1 C2 119.8(4) . . ?
C6 C1 C7 131.9(4) . . ?
C2 C1 C7 108.3(3) . . ?
C1 C2 C3 122.6(4) . . ?
C1 C2 N1 109.8(3) . . ?
C3 C2 N1 127.5(4) . . ?
C4 C3 C2 116.3(5) . . ?
C4 C3 H3 121.9 . . ?
C2 C3 H3 121.9 . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C1 C7 C8 101.8(3) . . ?
C1 C7 C9 114.3(3) . . ?
C8 C7 C9 107.1(3) . . ?
C1 C7 C10 118.2(3) . . ?
C8 C7 C10 111.9(3) . . ?
C9 C7 C10 103.3(3) . . ?
O2 C8 N1 125.6(4) . . ?
O2 C8 C7 125.5(4) . . ?
N1 C8 C7 108.9(3) . . ?
O1 C9 C12 128.4(4) . . ?
O1 C9 C7 123.9(4) . . ?
C12 C9 C7 107.7(3) . . ?
O3 C10 C11 106.2(3) . . ?
O3 C10 C7 114.4(3) . . ?
C11 C10 C7 104.2(3) . . ?
O3 C10 H10 110.6 . . ?
C11 C10 H10 110.6 . . ?
C7 C10 H10 110.6 . . ?
C12 C11 C10 113.2(4) . . ?
C12 C11 H11 123.4 . . ?
C10 C11 H11 123.4 . . ?
C11 C12 C9 111.4(4) . . ?
C11 C12 H12 124.3 . . ?
C9 C12 H12 124.3 . . ?
C10 O3 H3O 106(4) . . ?
C8 N1 C2 111.2(4) . . ?
C8 N1 H1N 124(3) . . ?
C2 N1 H1N 125(3) . . ?

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
C6 C1 C2 C3 -2.1(5) . . . . ?
C7 C1 C2 C3 178.4(3) . . . . ?
C6 C1 C2 N1 178.9(3) . . . . ?
C7 C1 C2 N1 -0.7(4) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
N1 C2 C3 C4 -179.9(4) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C1 -0.1(7) . . . . ?
C2 C1 C6 C5 1.5(6) . . . . ?
C7 C1 C6 C5 -179.1(4) . . . . ?
C6 C1 C7 C8 -179.5(4) . . . . ?
C2 C1 C7 C8 0.0(4) . . . . ?
C6 C1 C7 C9 -64.5(5) . . . . ?
C2 C1 C7 C9 115.0(4) . . . . ?
C6 C1 C7 C10 57.5(5) . . . . ?
C2 C1 C7 C10 -123.0(3) . . . . ?
C1 C7 C8 O2 -179.4(4) . . . . ?
C9 C7 C8 O2 60.4(5) . . . . ?
C10 C7 C8 O2 -52.2(5) . . . . ?
C1 C7 C8 N1 0.7(4) . . . . ?
C9 C7 C8 N1 -119.5(4) . . . . ?
C10 C7 C8 N1 127.9(3) . . . . ?
C1 C7 C9 O1 -48.8(6) . . . . ?
C8 C7 C9 O1 63.1(5) . . . . ?
C10 C7 C9 O1 -178.6(4) . . . . ?
C1 C7 C9 C12 132.6(3) . . . . ?
C8 C7 C9 C12 -115.5(3) . . . . ?
C10 C7 C9 C12 2.8(4) . . . . ?
C1 C7 C10 O3 -15.2(5) . . . . ?
C8 C7 C10 O3 -132.9(3) . . . . ?
C9 C7 C10 O3 112.2(3) . . . . ?
C1 C7 C10 C11 -130.7(3) . . . . ?
C8 C7 C10 C11 111.5(3) . . . . ?
C9 C7 C10 C11 -3.4(4) . . . . ?
O3 C10 C11 C12 -118.2(4) . . . . ?
C7 C10 C11 C12 3.1(5) . . . . ?
C10 C11 C12 C9 -1.3(5) . . . . ?
O1 C9 C12 C11 -179.6(5) . . . . ?
C7 C9 C12 C11 -1.1(5) . . . . ?
O2 C8 N1 C2 178.9(4) . . . . ?
C7 C8 N1 C2 -1.2(4) . . . . ?
C1 C2 N1 C8 1.2(4) . . . . ?
C3 C2 N1 C8 -177.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O2 0.94(7) 1.91(7) 2.638(4) 132(5) 3_645 yes
N1 H1N O3 0.88(4) 1.94(5) 2.815(5) 170(4) 1_455 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_KB14_0m
_database_code_depnum_ccdc_archive 'CCDC 2104601'
loop_
_audit_author_name
_audit_author_address
'Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.5740(7)
_cell_length_b                   8.6042(6)
_cell_length_c                   14.8471(8)
_cell_angle_alpha                102.836(3)
_cell_angle_beta                 101.585(8)
_cell_angle_gamma                99.182(9)
_cell_volume                     783.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.97

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10367
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3214
_reflns_number_gt                2187
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0717P)²+0.0353P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3214
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
C1 C 0.5694(3) 0.1579(2) 0.75140(13) 0.0385(4) Uani 1 1 d . . . . .
C2 C 0.3969(3) 0.0215(2) 0.71892(14) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.2422(4) -0.0043(2) 0.76841(16) 0.0530(6) Uani 1 1 d . . . . .
H3 H 0.131059 -0.095566 0.746123 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2604(4) 0.1107(3) 0.85160(17) 0.0634(7) Uani 1 1 d . . . . .
H4 H 0.158817 0.096938 0.886261 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4266(4) 0.2476(3) 0.88571(16) 0.0638(7) Uani 1 1 d . . . . .
H5 H 0.433125 0.323530 0.942182 0.077 Uiso 1 1 calc R U . . .
C6 C 0.5820(4) 0.2724(2) 0.83696(14) 0.0524(6) Uani 1 1 d . . . . .
H6 H 0.693256 0.363610 0.860512 0.063 Uiso 1 1 calc R U . . .
C7 C 0.6966(3) 0.14149(19) 0.68270(13) 0.0371(4) Uani 1 1 d . . . . .
C8 C 0.5995(3) 0.0008(2) 0.61474(14) 0.0436(5) Uani 1 1 d . . . . .
H8 H 0.648610 -0.040681 0.561751 0.052 Uiso 1 1 calc R U . . .
C9 C 0.9007(3) 0.2520(2) 0.68713(13) 0.0380(4) Uani 1 1 d . . . . .
H9 H 0.994364 0.265945 0.749975 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8901(3) 0.42696(18) 0.67556(12) 0.0305(4) Uani 1 1 d . . . . .
C11 C 1.0648(3) 0.4623(2) 0.62280(14) 0.0402(4) Uani 1 1 d . . . . .
C12 C 1.1123(3) 0.3060(2) 0.58117(17) 0.0530(5) Uani 1 1 d . . . . .
H12 H 1.195580 0.289399 0.537571 0.064 Uiso 1 1 calc R U . . .
C13 C 1.0190(3) 0.1917(2) 0.61494(15) 0.0481(5) Uani 1 1 d . . . . .
H13 H 1.026155 0.082691 0.595452 0.058 Uiso 1 1 calc R U . . .
C14 C 0.9020(3) 0.55925(19) 0.76240(12) 0.0332(4) Uani 1 1 d . . . . .
C15 C 0.7300(3) 0.63198(19) 0.74468(12) 0.0352(4) Uani 1 1 d . . . . .
C16 C 0.6823(3) 0.43128(18) 0.60730(12) 0.0294(4) Uani 1 1 d . . . . .
C17 C 1.0452(4) 0.6115(2) 0.85002(14) 0.0504(5) Uani 1 1 d . . . . .
H17 H 1.162473 0.564808 0.862795 0.061 Uiso 1 1 calc R U . . .
C18 C 1.0099(4) 0.7361(3) 0.91914(15) 0.0645(7) Uani 1 1 d . . . . .
H18 H 1.104539 0.772862 0.978883 0.077 Uiso 1 1 calc R U . . .
C19 C 0.8383(5) 0.8050(3) 0.90035(15) 0.0636(7) Uani 1 1 d . . . . .
H19 H 0.817895 0.887641 0.947790 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6939(4) 0.7549(2) 0.81242(15) 0.0541(6) Uani 1 1 d . . . . .
H20 H 0.577448 0.802356 0.799660 0.065 Uiso 1 1 calc R U . . .
O1 O 1.1447(2) 0.59678(16) 0.61941(11) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.6029(2) 0.34207(14) 0.52805(9) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.4194(3) -0.07146(19) 0.63495(13) 0.0471(4) Uani 1 1 d . . . . .
H1N H 0.340(4) -0.167(3) 0.5993(15) 0.061(7) Uiso 1 1 d . . . . .
N2 N 0.6065(3) 0.55655(17) 0.65166(11) 0.0387(4) Uani 1 1 d . . . . .
H2N H 0.492(3) 0.587(2) 0.6222(15) 0.058 Uiso 1 1 d . 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
C1 C6 1.403(3) . ?
C1 C2 1.414(3) . ?
C1 C7 1.441(3) . ?
C2 N1 1.373(2) . ?
C2 C3 1.387(3) . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.358(3) . ?
C7 C9 1.496(2) . ?
C8 N1 1.367(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.496(3) . ?
C9 C10 1.563(2) . ?
C9 H9 0.9800 . ?
C10 C14 1.498(2) . ?
C10 C16 1.540(2) . ?
C10 C11 1.543(2) . ?
C11 O1 1.208(2) . ?
C11 C12 1.460(3) . ?
C12 C13 1.321(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C17 1.376(2) . ?
C14 C15 1.385(2) . ?
C15 C20 1.375(2) . ?
C15 N2 1.404(2) . ?
C16 O2 1.213(2) . ?
C16 N2 1.353(2) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1N 0.89(2) . ?
N2 H2N 0.90(2) . ?

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
C6 C1 C2 118.13(18) . . ?
C6 C1 C7 134.96(18) . . ?
C2 C1 C7 106.90(16) . . ?
N1 C2 C3 129.88(19) . . ?
N1 C2 C1 107.22(17) . . ?
C3 C2 C1 122.89(19) . . ?
C4 C3 C2 117.1(2) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C8 C7 C1 106.19(17) . . ?
C8 C7 C9 126.48(18) . . ?
C1 C7 C9 127.27(17) . . ?
C7 C8 N1 110.64(18) . . ?
C7 C8 H8 124.7 . . ?
N1 C8 H8 124.7 . . ?
C7 C9 C13 116.09(16) . . ?
C7 C9 C10 117.42(14) . . ?
C13 C9 C10 102.18(14) . . ?
C7 C9 H9 106.8 . . ?
C13 C9 H9 106.8 . . ?
C10 C9 H9 106.8 . . ?
C14 C10 C16 102.75(13) . . ?
C14 C10 C11 114.54(14) . . ?
C16 C10 C11 104.87(13) . . ?
C14 C10 C9 118.40(13) . . ?
C16 C10 C9 112.80(13) . . ?
C11 C10 C9 102.99(13) . . ?
O1 C11 C12 128.33(18) . . ?
O1 C11 C10 124.52(17) . . ?
C12 C11 C10 107.15(15) . . ?
C13 C12 C11 109.55(18) . . ?
C13 C12 H12 125.2 . . ?
C11 C12 H12 125.2 . . ?
C12 C13 C9 114.50(17) . . ?
C12 C13 H13 122.7 . . ?
C9 C13 H13 122.7 . . ?
C17 C14 C15 119.83(17) . . ?
C17 C14 C10 131.44(16) . . ?
C15 C14 C10 108.73(15) . . ?
C20 C15 C14 122.30(18) . . ?
C20 C15 N2 128.58(18) . . ?
C14 C15 N2 109.10(15) . . ?
O2 C16 N2 126.14(16) . . ?
O2 C16 C10 126.90(15) . . ?
N2 C16 C10 106.95(14) . . ?
C14 C17 C18 118.2(2) . . ?
C14 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.5(2) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C15 C20 C19 117.2(2) . . ?
C15 C20 H20 121.4 . . ?
C19 C20 H20 121.4 . . ?
C8 N1 C2 109.04(17) . . ?
C8 N1 H1N 122.4(15) . . ?
C2 N1 H1N 128.5(15) . . ?
C16 N2 C15 112.34(15) . . ?
C16 N2 H2N 121.9(13) . . ?
C15 N2 H2N 125.8(13) . . ?

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
C6 C1 C2 N1 179.95(16) . . . . ?
C7 C1 C2 N1 -0.19(19) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 179.15(16) . . . . ?
N1 C2 C3 C4 179.98(19) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C7 C1 C6 C5 -179.82(19) . . . . ?
C6 C1 C7 C8 179.5(2) . . . . ?
C2 C1 C7 C8 -0.32(19) . . . . ?
C6 C1 C7 C9 2.3(3) . . . . ?
C2 C1 C7 C9 -177.57(15) . . . . ?
C1 C7 C8 N1 0.7(2) . . . . ?
C9 C7 C8 N1 178.00(15) . . . . ?
C8 C7 C9 C13 -6.8(3) . . . . ?
C1 C7 C9 C13 169.96(16) . . . . ?
C8 C7 C9 C10 114.5(2) . . . . ?
C1 C7 C9 C10 -68.8(2) . . . . ?
C7 C9 C10 C14 86.4(2) . . . . ?
C13 C9 C10 C14 -145.40(16) . . . . ?
C7 C9 C10 C16 -33.6(2) . . . . ?
C13 C9 C10 C16 94.65(17) . . . . ?
C7 C9 C10 C11 -146.09(16) . . . . ?
C13 C9 C10 C11 -17.86(17) . . . . ?
C14 C10 C11 O1 -31.6(2) . . . . ?
C16 C10 C11 O1 80.3(2) . . . . ?
C9 C10 C11 O1 -161.51(19) . . . . ?
C14 C10 C11 C12 147.63(16) . . . . ?
C16 C10 C11 C12 -100.52(16) . . . . ?
C9 C10 C11 C12 17.70(19) . . . . ?
O1 C11 C12 C13 168.8(2) . . . . ?
C10 C11 C12 C13 -10.4(2) . . . . ?
C11 C12 C13 C9 -2.2(3) . . . . ?
C7 C9 C13 C12 142.44(18) . . . . ?
C10 C9 C13 C12 13.4(2) . . . . ?
C16 C10 C14 C17 176.77(18) . . . . ?
C11 C10 C14 C17 -70.1(2) . . . . ?
C9 C10 C14 C17 51.7(3) . . . . ?
C16 C10 C14 C15 -1.85(16) . . . . ?
C11 C10 C14 C15 111.26(16) . . . . ?
C9 C10 C14 C15 -126.88(16) . . . . ?
C17 C14 C15 C20 -0.8(3) . . . . ?
C10 C14 C15 C20 177.99(16) . . . . ?
C17 C14 C15 N2 -179.13(16) . . . . ?
C10 C14 C15 N2 -0.32(19) . . . . ?
C14 C10 C16 O2 -177.91(15) . . . . ?
C11 C10 C16 O2 62.0(2) . . . . ?
C9 C10 C16 O2 -49.3(2) . . . . ?
C14 C10 C16 N2 3.44(16) . . . . ?
C11 C10 C16 N2 -116.60(15) . . . . ?
C9 C10 C16 N2 132.06(15) . . . . ?
C15 C14 C17 C18 0.8(3) . . . . ?
C10 C14 C17 C18 -177.72(18) . . . . ?
C14 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C14 C15 C20 C19 0.3(3) . . . . ?
N2 C15 C20 C19 178.23(18) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C7 C8 N1 C2 -0.9(2) . . . . ?
C3 C2 N1 C8 -178.64(19) . . . . ?
C1 C2 N1 C8 0.6(2) . . . . ?
O2 C16 N2 C15 177.42(15) . . . . ?
C10 C16 N2 C15 -3.92(19) . . . . ?
C20 C15 N2 C16 -175.38(18) . . . . ?
C14 C15 N2 C16 2.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O1 0.89(2) 2.34(2) 3.059(2) 138.6(19) 1_445 yes
N1 H1N O2 0.89(2) 2.28(2) 2.923(2) 129.6(19) 2_656 yes
N2 H2N O1 0.90(2) 2.29(2) 3.065(2) 144.1(18) 1_455 yes
N2 H2N O2 0.90(2) 2.43(2) 3.1173(19) 133.5(18) 2_666 yes

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_KA1120_0m
_database_code_depnum_ccdc_archive 'CCDC 2104600'
loop_
_audit_author_name
_audit_author_address
' Dr. B. Sridhar'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N O2'
_chemical_formula_sum            'C25 H21 N O2'
_chemical_formula_weight         367.43

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                   12.2675(6)
_cell_length_b                   11.9199(7)
_cell_length_c                   12.9994(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.172(3)
_cell_angle_gamma                90
_cell_volume                     1895.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.14

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6838
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40343
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.204
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4669
_reflns_number_gt                3060
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.6396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4669
_refine_ls_number_parameters     259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.015
_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
C1 C 0.38408(13) 0.23891(14) 0.67489(12) 0.0339(4) Uani 1 1 d . . . . .
C2 C 0.48281(14) 0.22653(16) 0.73399(15) 0.0452(4) Uani 1 1 d . . . . .
H2 H 0.504792 0.282077 0.781281 0.054 Uiso 1 1 calc R U . . .
C3 C 0.54860(16) 0.13409(19) 0.72410(17) 0.0548(5) Uani 1 1 d . . . . .
H3 H 0.614209 0.127473 0.764222 0.066 Uiso 1 1 calc R U . . .
C4 C 0.51651(17) 0.05201(18) 0.65463(17) 0.0580(6) Uani 1 1 d . . . . .
H4 H 0.560314 -0.010922 0.648226 0.070 Uiso 1 1 calc R U . . .
C5 C 0.41998(16) 0.06174(16) 0.59412(15) 0.0500(5) Uani 1 1 d . . . . .
H5 H 0.398781 0.006154 0.546598 0.060 Uiso 1 1 calc R U . . .
C6 C 0.35477(14) 0.15557(14) 0.60502(13) 0.0372(4) Uani 1 1 d . . . . .
C7 C 0.18355(14) 0.24073(14) 0.55997(13) 0.0374(4) Uani 1 1 d . . . . .
C8 C 0.20321(12) 0.32751(13) 0.62918(12) 0.0328(4) Uani 1 1 d . . . . .
C9 C 0.31163(12) 0.33973(13) 0.68997(12) 0.0312(3) Uani 1 1 d . . . . .
C10 C 0.08320(16) 0.22819(18) 0.50501(15) 0.0526(5) Uani 1 1 d . . . . .
H10 H 0.071557 0.168986 0.458918 0.063 Uiso 1 1 calc R U . . .
C11 C 0.00088(16) 0.3039(2) 0.51906(16) 0.0577(6) Uani 1 1 d . . . . .
H11 H -0.066467 0.296144 0.482031 0.069 Uiso 1 1 calc R U . . .
C12 C 0.01807(15) 0.39101(19) 0.58784(16) 0.0521(5) Uani 1 1 d . . . . .
H12 H -0.037622 0.442072 0.597382 0.063 Uiso 1 1 calc R U . . .
C13 C 0.11777(14) 0.40237(16) 0.64242(14) 0.0421(4) Uani 1 1 d . . . . .
H13 H 0.128521 0.461135 0.689123 0.051 Uiso 1 1 calc R U . . .
C14 C 0.29335(13) 0.34551(15) 0.80667(13) 0.0371(4) Uani 1 1 d . . . . .
C15 C 0.33654(15) 0.45162(17) 0.84700(15) 0.0473(5) Uani 1 1 d . . . . .
H15 H 0.336052 0.474183 0.915447 0.057 Uiso 1 1 calc R U . . .
C16 C 0.37648(15) 0.51144(16) 0.77314(15) 0.0478(5) Uani 1 1 d . . . . .
H16 H 0.404464 0.583312 0.784110 0.057 Uiso 1 1 calc R U . . .
C17 C 0.37326(13) 0.45455(14) 0.67013(13) 0.0361(4) Uani 1 1 d . . . . .
H17 H 0.448478 0.436804 0.655129 0.043 Uiso 1 1 calc R U . . .
C18 C 0.33523(13) 0.50513(14) 0.48621(14) 0.0381(4) Uani 1 1 d . . . . .
C19 C 0.29588(15) 0.58233(17) 0.41220(16) 0.0503(5) Uani 1 1 d . . . . .
H19 H 0.267634 0.650592 0.432457 0.060 Uiso 1 1 calc R U . . .
C20 C 0.29881(15) 0.5575(2) 0.30887(16) 0.0571(6) Uani 1 1 d . . . . .
H20 H 0.272409 0.610377 0.260666 0.068 Uiso 1 1 calc R U . . .
C21 C 0.33954(15) 0.45692(19) 0.27367(15) 0.0510(5) Uani 1 1 d . . . . .
C22 C 0.38182(15) 0.38097(16) 0.34707(15) 0.0453(4) Uani 1 1 d . . . . .
C23 C 0.37964(14) 0.40615(15) 0.45152(14) 0.0417(4) Uani 1 1 d . . . . .
H23 H 0.408991 0.354805 0.499784 0.050 Uiso 1 1 calc R U . . .
C24 C 0.3348(2) 0.4337(3) 0.15906(17) 0.0776(8) Uani 1 1 d . . . . .
H24A H 0.304794 0.497632 0.122109 0.116 Uiso 1 1 calc R U . . .
H24B H 0.289401 0.369393 0.143548 0.116 Uiso 1 1 calc R U . . .
H24C H 0.407176 0.419257 0.138778 0.116 Uiso 1 1 calc R U . . .
C25 C 0.4291(2) 0.2702(2) 0.3183(2) 0.0725(7) Uani 1 1 d . . . . .
H25A H 0.382895 0.210581 0.339062 0.109 Uiso 1 1 calc R U . . .
H25B H 0.500768 0.261832 0.352331 0.109 Uiso 1 1 calc R U . . .
H25C H 0.434013 0.267188 0.244929 0.109 Uiso 1 1 calc R U . . .
O1 O 0.26053(10) 0.16030(10) 0.54044(9) 0.0462(3) Uani 1 1 d . . . . .
O2 O 0.25119(11) 0.27200(12) 0.85419(10) 0.0540(4) Uani 1 1 d . . . . .
N1 N 0.32732(13) 0.52684(13) 0.59014(12) 0.0432(4) Uani 1 1 d . . . . .
H1N H 0.3008(16) 0.5918(18) 0.6055(15) 0.050(6) Uiso 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
C1 C6 1.376(2) . ?
C1 C2 1.394(2) . ?
C1 C9 1.516(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.370(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 O1 1.380(2) . ?
C7 C8 1.381(2) . ?
C7 O1 1.382(2) . ?
C7 C10 1.386(2) . ?
C8 C13 1.397(2) . ?
C8 C9 1.504(2) . ?
C9 C14 1.551(2) . ?
C9 C17 1.594(2) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O2 1.210(2) . ?
C14 C15 1.454(3) . ?
C15 C16 1.319(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.499(2) . ?
C16 H16 0.9300 . ?
C17 N1 1.434(2) . ?
C17 H17 0.9800 . ?
C18 N1 1.386(2) . ?
C18 C23 1.388(2) . ?
C18 C19 1.392(2) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(3) . ?
C21 C24 1.512(3) . ?
C22 C23 1.393(3) . ?
C22 C25 1.501(3) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1N 0.87(2) . ?

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
C6 C1 C2 117.52(15) . . ?
C6 C1 C9 122.02(14) . . ?
C2 C1 C9 120.44(15) . . ?
C3 C2 C1 121.65(18) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 C3 C2 119.39(18) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.67(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.15(19) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 O1 122.63(15) . . ?
C1 C6 C5 121.61(16) . . ?
O1 C6 C5 115.75(16) . . ?
C8 C7 O1 123.37(14) . . ?
C8 C7 C10 121.56(17) . . ?
O1 C7 C10 115.07(16) . . ?
C7 C8 C13 117.51(15) . . ?
C7 C8 C9 121.39(14) . . ?
C13 C8 C9 121.09(15) . . ?
C8 C9 C1 111.08(13) . . ?
C8 C9 C14 109.44(13) . . ?
C1 C9 C14 106.83(13) . . ?
C8 C9 C17 114.20(13) . . ?
C1 C9 C17 111.74(12) . . ?
C14 C9 C17 102.95(12) . . ?
C11 C10 C7 119.59(19) . . ?
C11 C10 H10 120.2 . . ?
C7 C10 H10 120.2 . . ?
C10 C11 C12 120.10(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.86(18) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 121.38(18) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
O2 C14 C15 127.16(17) . . ?
O2 C14 C9 124.39(16) . . ?
C15 C14 C9 108.44(15) . . ?
C16 C15 C14 110.66(17) . . ?
C16 C15 H15 124.7 . . ?
C14 C15 H15 124.7 . . ?
C15 C16 C17 114.75(17) . . ?
C15 C16 H16 122.6 . . ?
C17 C16 H16 122.6 . . ?
N1 C17 C16 111.06(15) . . ?
N1 C17 C9 117.87(13) . . ?
C16 C17 C9 103.06(14) . . ?
N1 C17 H17 108.1 . . ?
C16 C17 H17 108.1 . . ?
C9 C17 H17 108.1 . . ?
N1 C18 C23 122.15(16) . . ?
N1 C18 C19 120.33(17) . . ?
C23 C18 C19 117.50(17) . . ?
C20 C19 C18 119.96(19) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 122.79(19) . . ?
C19 C20 H20 118.6 . . ?
C21 C20 H20 118.6 . . ?
C22 C21 C20 117.51(18) . . ?
C22 C21 C24 122.9(2) . . ?
C20 C21 C24 119.6(2) . . ?
C21 C22 C23 119.79(19) . . ?
C21 C22 C25 122.29(19) . . ?
C23 C22 C25 117.91(19) . . ?
C18 C23 C22 122.38(17) . . ?
C18 C23 H23 118.8 . . ?
C22 C23 H23 118.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C6 O1 C7 118.05(13) . . ?
C18 N1 C17 122.89(15) . . ?
C18 N1 H1N 116.4(13) . . ?
C17 N1 H1N 120.2(13) . . ?

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
C6 C1 C2 C3 -0.6(3) . . . . ?
C9 C1 C2 C3 177.99(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C2 C1 C6 O1 -178.16(16) . . . . ?
C9 C1 C6 O1 3.3(2) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C9 C1 C6 C5 -177.87(16) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 O1 178.81(17) . . . . ?
O1 C7 C8 C13 -179.30(15) . . . . ?
C10 C7 C8 C13 0.3(3) . . . . ?
O1 C7 C8 C9 -0.7(2) . . . . ?
C10 C7 C8 C9 178.97(16) . . . . ?
C7 C8 C9 C1 -7.7(2) . . . . ?
C13 C8 C9 C1 170.90(15) . . . . ?
C7 C8 C9 C14 -125.41(16) . . . . ?
C13 C8 C9 C14 53.2(2) . . . . ?
C7 C8 C9 C17 119.80(16) . . . . ?
C13 C8 C9 C17 -61.6(2) . . . . ?
C6 C1 C9 C8 6.5(2) . . . . ?
C2 C1 C9 C8 -172.06(15) . . . . ?
C6 C1 C9 C14 125.79(16) . . . . ?
C2 C1 C9 C14 -52.76(19) . . . . ?
C6 C1 C9 C17 -122.32(16) . . . . ?
C2 C1 C9 C17 59.1(2) . . . . ?
C8 C7 C10 C11 0.2(3) . . . . ?
O1 C7 C10 C11 179.89(17) . . . . ?
C7 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?
C7 C8 C13 C12 -0.7(3) . . . . ?
C9 C8 C13 C12 -179.33(16) . . . . ?
C8 C9 C14 O2 60.4(2) . . . . ?
C1 C9 C14 O2 -60.0(2) . . . . ?
C17 C9 C14 O2 -177.79(16) . . . . ?
C8 C9 C14 C15 -120.45(15) . . . . ?
C1 C9 C14 C15 119.19(15) . . . . ?
C17 C9 C14 C15 1.37(16) . . . . ?
O2 C14 C15 C16 -179.96(18) . . . . ?
C9 C14 C15 C16 0.9(2) . . . . ?
C14 C15 C16 C17 -3.1(2) . . . . ?
C15 C16 C17 N1 130.93(18) . . . . ?
C15 C16 C17 C9 3.8(2) . . . . ?
C8 C9 C17 N1 -7.0(2) . . . . ?
C1 C9 C17 N1 120.17(16) . . . . ?
C14 C9 C17 N1 -125.52(15) . . . . ?
C8 C9 C17 C16 115.70(15) . . . . ?
C1 C9 C17 C16 -117.15(14) . . . . ?
C14 C9 C17 C16 -2.84(15) . . . . ?
N1 C18 C19 C20 -176.58(17) . . . . ?
C23 C18 C19 C20 2.0(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C22 -2.1(3) . . . . ?
C19 C20 C21 C24 176.99(19) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C24 C21 C22 C23 -177.46(18) . . . . ?
C20 C21 C22 C25 -179.34(18) . . . . ?
C24 C21 C22 C25 1.6(3) . . . . ?
N1 C18 C23 C22 176.05(16) . . . . ?
C19 C18 C23 C22 -2.5(2) . . . . ?
C21 C22 C23 C18 0.7(3) . . . . ?
C25 C22 C23 C18 -178.41(17) . . . . ?
C1 C6 O1 C7 -12.3(2) . . . . ?
C5 C6 O1 C7 168.79(15) . . . . ?
C8 C7 O1 C6 11.0(2) . . . . ?
C10 C7 O1 C6 -168.64(15) . . . . ?
C23 C18 N1 C17 6.1(3) . . . . ?
C19 C18 N1 C17 -175.39(16) . . . . ?
C16 C17 N1 C18 166.21(16) . . . . ?
C9 C17 N1 C18 -75.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N O2 0.87(2) 2.31(2) 3.177(2) 173.9(18) 2_556 yes

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.046

