# Supplementary Information (SI) for Dalton Transactions.
# 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_hqbic_3_0m
_database_code_depnum_ccdc_archive 'CCDC 2387451'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 N3 O'
_chemical_formula_sum            'C16 H11 N3 O'
_chemical_formula_weight         261.28

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   41.92(4)
_cell_length_b                   5.948(5)
_cell_length_c                   9.899(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.88(4)
_cell_angle_gamma                90
_cell_volume                     2460(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    1274
_cell_measurement_theta_min      0.982
_cell_measurement_theta_max      0.984

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9972
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_av_R_equivalents  0.1177
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.926
_diffrn_reflns_theta_max         25.894
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2261
_reflns_number_gt                1274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          '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)+(0.0651P)²+2.4916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0055(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1544
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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
O1 O 0.53383(5) 1.1287(4) 0.6532(3) 0.0640(8) Uani 1 1 d . . . . .
H1 H 0.519413 1.084573 0.598408 0.096 Uiso 1 1 calc R U . . .
N3 N 0.52932(6) 0.7746(5) 0.4886(3) 0.0488(8) Uani 1 1 d . . . . .
N2 N 0.65492(6) 0.4895(5) 0.7741(3) 0.0432(7) Uani 1 1 d . . . . .
H2 H 0.650191 0.528679 0.853647 0.052 Uiso 1 1 calc R U . . .
N1 N 0.65190(6) 0.4638(5) 0.5545(3) 0.0461(8) Uani 1 1 d . . . . .
C11 C 0.55910(7) 0.9926(6) 0.6503(4) 0.0463(9) Uani 1 1 d . . . . .
C10 C 0.58609(8) 1.0326(6) 0.7305(4) 0.0520(10) Uani 1 1 d . . . . .
H10 H 0.587374 1.158349 0.786514 0.062 Uiso 1 1 calc R U . . .
C9 C 0.61205(7) 0.8869(6) 0.7302(4) 0.0481(9) Uani 1 1 d . . . . .
H9 H 0.630469 0.918150 0.786170 0.058 Uiso 1 1 calc R U . . .
C8 C 0.61136(7) 0.7010(6) 0.6509(3) 0.0424(9) Uani 1 1 d . . . . .
C13 C 0.58350(7) 0.6565(5) 0.5652(3) 0.0390(8) Uani 1 1 d . . . . .
C12 C 0.55744(7) 0.8039(6) 0.5660(3) 0.0430(9) Uani 1 1 d . . . . .
C16 C 0.52729(8) 0.5973(6) 0.4125(4) 0.0530(10) Uani 1 1 d . . . . .
H16 H 0.508336 0.574111 0.358430 0.064 Uiso 1 1 calc R U . . .
C15 C 0.55140(8) 0.4402(6) 0.4063(4) 0.0527(10) Uani 1 1 d . . . . .
H15 H 0.548396 0.315443 0.349994 0.063 Uiso 1 1 calc R U . . .
C14 C 0.57940(8) 0.4692(6) 0.4828(4) 0.0475(9) Uani 1 1 d . . . . .
H14 H 0.595750 0.364058 0.479954 0.057 Uiso 1 1 calc R U . . .
C2 C 0.63918(7) 0.5503(6) 0.6570(3) 0.0424(8) Uani 1 1 d . . . . .
C3 C 0.67979(7) 0.3545(5) 0.7460(3) 0.0419(8) Uani 1 1 d . . . . .
C4 C 0.70319(7) 0.2455(6) 0.8272(4) 0.0518(10) Uani 1 1 d . . . . .
H4 H 0.704217 0.256536 0.921159 0.062 Uiso 1 1 calc R U . . .
C5 C 0.72471(8) 0.1212(6) 0.7642(4) 0.0557(10) Uani 1 1 d . . . . .
H5 H 0.740601 0.042539 0.815767 0.067 Uiso 1 1 calc R U . . .
C6 C 0.72327(8) 0.1106(6) 0.6279(4) 0.0591(11) Uani 1 1 d . . . . .
H6 H 0.738597 0.027391 0.587100 0.071 Uiso 1 1 calc R U . . .
C7 C 0.70006(8) 0.2182(6) 0.5481(4) 0.0555(10) Uani 1 1 d . . . . .
H7 H 0.699412 0.208677 0.454173 0.067 Uiso 1 1 calc R U . . .
C1 C 0.67775(7) 0.3403(6) 0.6088(3) 0.0440(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.336(4) . ?
O1 H1 0.8200 . ?
N3 C16 1.294(4) . ?
N3 C12 1.361(4) . ?
N2 C2 1.335(4) . ?
N2 C3 1.363(4) . ?
N2 H2 0.8600 . ?
N1 C2 1.292(4) . ?
N1 C1 1.380(4) . ?
C11 C10 1.347(5) . ?
C11 C12 1.397(5) . ?
C10 C9 1.392(4) . ?
C10 H10 0.9300 . ?
C9 C8 1.355(5) . ?
C9 H9 0.9300 . ?
C8 C13 1.409(4) . ?
C8 C2 1.468(4) . ?
C13 C14 1.383(5) . ?
C13 C12 1.401(4) . ?
C16 C15 1.382(5) . ?
C16 H16 0.9300 . ?
C15 C14 1.352(5) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C3 C1 1.356(5) . ?
C3 C4 1.376(5) . ?
C4 C5 1.358(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.348(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.360(5) . ?
C6 H6 0.9300 . ?
C7 C1 1.363(4) . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 H1 109.5 . . ?
C16 N3 C12 116.3(3) . . ?
C2 N2 C3 108.2(3) . . ?
C2 N2 H2 125.9 . . ?
C3 N2 H2 125.9 . . ?
C2 N1 C1 105.6(3) . . ?
O1 C11 C10 120.6(3) . . ?
O1 C11 C12 120.0(3) . . ?
C10 C11 C12 119.4(3) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C8 C9 C10 122.1(3) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C9 C8 C13 118.5(3) . . ?
C9 C8 C2 119.8(3) . . ?
C13 C8 C2 121.6(3) . . ?
C14 C13 C12 116.7(3) . . ?
C14 C13 C8 124.2(3) . . ?
C12 C13 C8 119.1(3) . . ?
N3 C12 C11 115.8(3) . . ?
N3 C12 C13 123.7(3) . . ?
C11 C12 C13 120.4(3) . . ?
N3 C16 C15 124.4(3) . . ?
N3 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C14 C15 C16 119.5(4) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
N1 C2 N2 111.6(3) . . ?
N1 C2 C8 126.2(3) . . ?
N2 C2 C8 122.2(3) . . ?
C1 C3 N2 104.9(3) . . ?
C1 C3 C4 122.4(3) . . ?
N2 C3 C4 132.6(3) . . ?
C5 C4 C3 117.2(4) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C1 118.6(4) . . ?
C6 C7 H7 120.7 . . ?
C1 C7 H7 120.7 . . ?
C3 C1 C7 119.2(3) . . ?
C3 C1 N1 109.7(3) . . ?
C7 C1 N1 131.1(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
O1 C11 C10 C9 178.2(3) . . . . ?
C12 C11 C10 C9 -0.4(5) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
C10 C9 C8 C13 0.8(5) . . . . ?
C10 C9 C8 C2 -178.6(3) . . . . ?
C9 C8 C13 C14 -177.9(3) . . . . ?
C2 C8 C13 C14 1.5(5) . . . . ?
C9 C8 C13 C12 -0.8(5) . . . . ?
C2 C8 C13 C12 178.6(3) . . . . ?
C16 N3 C12 C11 -178.4(3) . . . . ?
C16 N3 C12 C13 0.9(5) . . . . ?
O1 C11 C12 N3 1.2(5) . . . . ?
C10 C11 C12 N3 179.7(3) . . . . ?
O1 C11 C12 C13 -178.2(3) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C14 C13 C12 N3 -1.8(5) . . . . ?
C8 C13 C12 N3 -179.1(3) . . . . ?
C14 C13 C12 C11 177.5(3) . . . . ?
C8 C13 C12 C11 0.2(5) . . . . ?
C12 N3 C16 C15 0.3(5) . . . . ?
N3 C16 C15 C14 -0.5(6) . . . . ?
C16 C15 C14 C13 -0.5(5) . . . . ?
C12 C13 C14 C15 1.5(5) . . . . ?
C8 C13 C14 C15 178.6(3) . . . . ?
C1 N1 C2 N2 -0.5(4) . . . . ?
C1 N1 C2 C8 178.3(3) . . . . ?
C3 N2 C2 N1 0.3(4) . . . . ?
C3 N2 C2 C8 -178.6(3) . . . . ?
C9 C8 C2 N1 -135.1(4) . . . . ?
C13 C8 C2 N1 45.5(5) . . . . ?
C9 C8 C2 N2 43.6(5) . . . . ?
C13 C8 C2 N2 -135.8(3) . . . . ?
C2 N2 C3 C1 0.0(4) . . . . ?
C2 N2 C3 C4 -179.5(4) . . . . ?
C1 C3 C4 C5 0.3(5) . . . . ?
N2 C3 C4 C5 179.7(3) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C5 C6 C7 C1 0.2(6) . . . . ?
N2 C3 C1 C7 178.8(3) . . . . ?
C4 C3 C1 C7 -1.6(5) . . . . ?
N2 C3 C1 N1 -0.3(4) . . . . ?
C4 C3 C1 N1 179.3(3) . . . . ?
C6 C7 C1 C3 1.4(5) . . . . ?
C6 C7 C1 N1 -179.8(3) . . . . ?
C2 N1 C1 C3 0.5(4) . . . . ?
C2 N1 C1 C7 -178.4(4) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.063



####################################################################### 
# 
# 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_bt_tbaf_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2387452'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 N2 O S'
_chemical_formula_sum            'C16 H10 N2 O S'
_chemical_formula_weight         278.32

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'
S S 0.1246 0.1234 '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                   8.0639(10)
_cell_length_b                   8.1559(11)
_cell_length_c                   10.4359(14)
_cell_angle_alpha                99.948(5)
_cell_angle_beta                 108.024(4)
_cell_angle_gamma                96.408(5)
_cell_volume                     632.80(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    1768
_cell_measurement_theta_min      0.946
_cell_measurement_theta_max      0.956

_exptl_crystal_description       Rod
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20160
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.698
_diffrn_reflns_theta_max         27.529
_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             2915
_reflns_number_gt                1768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          '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)+(0.0508P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.01593(9) 0.48299(9) 0.18891(7) 0.0617(3) Uani 1 1 d . . . . .
O1 O 0.7836(2) 0.2992(2) 0.4119(2) 0.0651(5) Uani 1 1 d . . . . .
H1 H 0.873592 0.370027 0.453179 0.098 Uiso 1 1 calc R U . . .
N3 N 0.8340(3) 0.6415(2) 0.4796(2) 0.0492(5) Uani 1 1 d . . . . .
N1 N 0.1838(3) 0.7635(3) 0.2082(2) 0.0569(6) Uani 1 1 d . . . . .
C13 C 0.5207(3) 0.6390(3) 0.3576(2) 0.0443(5) Uani 1 1 d . . . . .
C8 C 0.3525(3) 0.5383(3) 0.2738(2) 0.0466(6) Uani 1 1 d . . . . .
C12 C 0.6675(3) 0.5576(3) 0.4027(2) 0.0443(5) Uani 1 1 d . . . . .
C16 C 0.8566(3) 0.8077(3) 0.5145(3) 0.0532(6) Uani 1 1 d . . . . .
H16 H 0.969586 0.866818 0.567171 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6456(3) 0.3776(3) 0.3663(3) 0.0490(6) Uani 1 1 d . . . . .
C14 C 0.5539(3) 0.8170(3) 0.3992(3) 0.0500(6) Uani 1 1 d . . . . .
H14 H 0.462298 0.877516 0.373738 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7207(3) 0.8998(3) 0.4768(3) 0.0554(6) Uani 1 1 d . . . . .
H15 H 0.743607 1.017108 0.504451 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1906(3) 0.6106(3) 0.2252(2) 0.0493(6) Uani 1 1 d . . . . .
C1 C 0.0095(3) 0.7910(3) 0.1659(3) 0.0553(7) Uani 1 1 d . . . . .
C9 C 0.3409(3) 0.3655(3) 0.2402(3) 0.0545(6) Uani 1 1 d . . . . .
H9 H 0.232279 0.299617 0.184576 0.065 Uiso 1 1 calc R U . . .
C10 C 0.4848(4) 0.2853(3) 0.2859(3) 0.0562(6) Uani 1 1 d . . . . .
H10 H 0.470740 0.168122 0.261354 0.067 Uiso 1 1 calc R U . . .
C3 C -0.1178(3) 0.6509(3) 0.1494(2) 0.0536(6) Uani 1 1 d . . . . .
C5 C -0.3450(4) 0.8149(5) 0.0910(3) 0.0794(10) Uani 1 1 d . . . . .
H5 H -0.463907 0.824903 0.066299 0.095 Uiso 1 1 calc R U . . .
C7 C -0.0436(4) 0.9423(4) 0.1433(3) 0.0740(9) Uani 1 1 d . . . . .
H7 H 0.039789 1.036306 0.153315 0.089 Uiso 1 1 calc R U . . .
C4 C -0.2968(4) 0.6622(4) 0.1117(3) 0.0665(8) Uani 1 1 d . . . . .
H4 H -0.381641 0.569001 0.100886 0.080 Uiso 1 1 calc R U . . .
C6 C -0.2203(5) 0.9524(5) 0.1061(3) 0.0826(9) Uani 1 1 d . . . . .
H6 H -0.256058 1.053915 0.090891 0.099 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
S1 C3 1.720(3) . ?
S1 C2 1.757(2) . ?
O1 C11 1.346(3) . ?
O1 H1 0.8200 . ?
N3 C16 1.318(3) . ?
N3 C12 1.362(3) . ?
N1 C2 1.294(3) . ?
N1 C1 1.393(3) . ?
C13 C14 1.411(3) . ?
C13 C12 1.416(3) . ?
C13 C8 1.431(3) . ?
C8 C9 1.378(3) . ?
C8 C2 1.475(3) . ?
C12 C11 1.427(3) . ?
C16 C15 1.393(3) . ?
C16 H16 0.9300 . ?
C11 C10 1.358(4) . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C1 C7 1.385(4) . ?
C1 C3 1.396(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C3 C4 1.391(4) . ?
C5 C6 1.372(5) . ?
C5 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C7 C6 1.372(4) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C2 89.32(12) . . ?
C11 O1 H1 109.5 . . ?
C16 N3 C12 117.2(2) . . ?
C2 N1 C1 111.1(2) . . ?
C14 C13 C12 116.2(2) . . ?
C14 C13 C8 124.9(2) . . ?
C12 C13 C8 118.9(2) . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C2 118.7(2) . . ?
C13 C8 C2 123.0(2) . . ?
N3 C12 C13 123.7(2) . . ?
N3 C12 C11 116.3(2) . . ?
C13 C12 C11 120.0(2) . . ?
N3 C16 C15 123.6(2) . . ?
N3 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
O1 C11 C10 119.9(2) . . ?
O1 C11 C12 120.2(2) . . ?
C10 C11 C12 119.9(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N1 C2 C8 126.3(2) . . ?
N1 C2 S1 115.03(19) . . ?
C8 C2 S1 118.67(18) . . ?
C7 C1 N1 125.8(3) . . ?
C7 C1 C3 119.4(2) . . ?
N1 C1 C3 114.7(2) . . ?
C8 C9 C10 122.8(2) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C4 C3 C1 120.8(3) . . ?
C4 C3 S1 129.4(2) . . ?
C1 C3 S1 109.80(19) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C7 C1 119.5(3) . . ?
C6 C7 H7 120.3 . . ?
C1 C7 H7 120.3 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?

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
C14 C13 C8 C9 179.3(2) . . . . ?
C12 C13 C8 C9 -0.1(3) . . . . ?
C14 C13 C8 C2 -2.5(4) . . . . ?
C12 C13 C8 C2 178.1(2) . . . . ?
C16 N3 C12 C13 0.8(3) . . . . ?
C16 N3 C12 C11 -179.8(2) . . . . ?
C14 C13 C12 N3 -1.2(3) . . . . ?
C8 C13 C12 N3 178.2(2) . . . . ?
C14 C13 C12 C11 179.5(2) . . . . ?
C8 C13 C12 C11 -1.1(3) . . . . ?
C12 N3 C16 C15 -0.1(4) . . . . ?
N3 C12 C11 O1 2.4(3) . . . . ?
C13 C12 C11 O1 -178.2(2) . . . . ?
N3 C12 C11 C10 -177.9(2) . . . . ?
C13 C12 C11 C10 1.5(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C8 C13 C14 C15 -178.6(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
N3 C16 C15 C14 -0.3(4) . . . . ?
C1 N1 C2 C8 -177.8(2) . . . . ?
C1 N1 C2 S1 0.9(3) . . . . ?
C9 C8 C2 N1 -156.7(2) . . . . ?
C13 C8 C2 N1 25.1(4) . . . . ?
C9 C8 C2 S1 24.7(3) . . . . ?
C13 C8 C2 S1 -153.53(19) . . . . ?
C3 S1 C2 N1 -0.5(2) . . . . ?
C3 S1 C2 C8 178.23(19) . . . . ?
C2 N1 C1 C7 177.6(3) . . . . ?
C2 N1 C1 C3 -0.8(3) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
C2 C8 C9 C10 -177.4(2) . . . . ?
O1 C11 C10 C9 179.0(2) . . . . ?
C12 C11 C10 C9 -0.7(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C7 C1 C3 C4 -0.6(4) . . . . ?
N1 C1 C3 C4 178.0(2) . . . . ?
C7 C1 C3 S1 -178.1(2) . . . . ?
N1 C1 C3 S1 0.5(3) . . . . ?
C2 S1 C3 C4 -177.2(2) . . . . ?
C2 S1 C3 C1 0.02(19) . . . . ?
N1 C1 C7 C6 -177.9(3) . . . . ?
C3 C1 C7 C6 0.5(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C1 C3 C4 C5 0.1(4) . . . . ?
S1 C3 C4 C5 177.1(2) . . . . ?
C1 C7 C6 C5 0.0(5) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_24domem_a_a
_database_code_depnum_ccdc_archive 'CCDC 2387455'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 O2, C16 H36 N, F, 4(H2 O)'
_chemical_formula_sum            'C29 H54 F N3 O6'
_chemical_formula_weight         559.75
_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'
F F 0.0171 0.0103 '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                   19.939(7)
_cell_length_b                   16.407(5)
_cell_length_c                   20.147(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.563(12)
_cell_angle_gamma                90
_cell_volume                     6591(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7721
_cell_measurement_temperature    299.00
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5478
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.2040 before and 0.0944 after correction.
The Ratio of minimum to maximum transmission is 0.7349.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             2448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2001
_diffrn_reflns_av_unetI/netI     0.1413
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            61333
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.256
_diffrn_ambient_temperature      299.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4095
_reflns_number_total             11601
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     732
_refine_ls_number_reflns         11601
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2421
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      0.868
_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)+(0.0967P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.2229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11B
 0.84 with sigma of 0.02
3.a Riding coordinates:
 O4(H4), O3(H3), N5(H5), O2(H2), O1(H1), N2(H2A), O7(H7A,H7B)
3.b Free rotating group:
 O12(H12A,H12B), O9(H9A,H9B), O10(H10A,H10B), O11(H11A,H11B), O6(H6A,H6B),
 O5(H5B,H5C), O8(H8A,H8B)
3.c Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C20(H20A,H20B), C19(H19A,H19B), C18(H18A,H18B),
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C59(H59A,H59B), C60(H60A,H60B),
  C61(H61A,H61B), C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C51(H51A,
 H51B), C53(H53A,H53B), C52(H52A,H52B), C47(H47A,H47B), C48(H48A,H48B),
 C49(H49A,H49B)
3.d Aromatic/amide H refined with riding coordinates:
 C33(H33), C34(H34), C35(H35), C36(H36), C42(H42), C41(H41), C39(H39), C7(H7),
 C6(H6), C5(H5A), C4(H4A), C10(H10), C12(H12), C13(H13)
3.e Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C17(H17A,H17B,H17C), C21(H21A,H21B,H21C), C25(H25A,H25B,
 H25C), C62(H62A,H62B,H62C), C58(H58A,H58B,H58C), C54(H54A,H54B,H54C), C50(H50A,
 H50B,H50C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O4 O 0.32200(12) -0.43434(18) 0.14950(13) 0.0832(9) Uani 1 1 d . . . . .
H4 H 0.281976 -0.444275 0.144304 0.125 Uiso 1 1 d R U . . .
O3 O 0.50500(13) -0.50229(17) 0.29099(13) 0.0828(9) Uani 1 1 d . . . . .
H3 H 0.525440 -0.481968 0.260070 0.124 Uiso 1 1 d R U . . .
N5 N 0.18027(15) -0.51683(17) 0.28677(15) 0.0579(8) Uani 1 1 d . . . . .
H5 H 0.186679 -0.535167 0.326294 0.069 Uiso 1 1 d R U . . .
N3 N 0.20225(15) -0.46986(18) 0.18479(15) 0.0582(8) Uani 1 1 d . . . . .
C33 C 0.0543(2) -0.5164(3) 0.2764(2) 0.0853(14) Uani 1 1 d . . . . .
H33 H 0.045276 -0.537642 0.318213 0.102 Uiso 1 1 calc R U . . .
C34 C 0.0033(2) -0.4949(3) 0.2325(3) 0.0955(16) Uani 1 1 d . . . . .
H34 H -0.041053 -0.501457 0.245153 0.115 Uiso 1 1 calc R U . . .
C35 C 0.0169(2) -0.4641(3) 0.1708(3) 0.0872(14) Uani 1 1 d . . . . .
H35 H -0.018703 -0.450317 0.142917 0.105 Uiso 1 1 calc R U . . .
C36 C 0.0813(2) -0.4528(3) 0.1487(2) 0.0766(13) Uani 1 1 d . . . . .
H36 H 0.089867 -0.431311 0.106918 0.092 Uiso 1 1 calc R U . . .
C32 C 0.11873(18) -0.5048(2) 0.25489(19) 0.0569(10) Uani 1 1 d . . . . .
C30 C 0.13346(19) -0.4754(2) 0.19208(19) 0.0584(10) Uani 1 1 d . . . . .
C31 C 0.22821(18) -0.4943(2) 0.24290(18) 0.0509(9) Uani 1 1 d . . . . .
C37 C 0.29952(18) -0.4966(2) 0.25579(17) 0.0467(9) Uani 1 1 d . . . . .
C42 C 0.32735(19) -0.5275(2) 0.31453(18) 0.0555(10) Uani 1 1 d . . . . .
H42 H 0.298879 -0.547334 0.347065 0.067 Uiso 1 1 calc R U . . .
C41 C 0.3955(2) -0.5296(2) 0.32579(19) 0.0621(11) Uani 1 1 d . . . . .
H41 H 0.412658 -0.551392 0.365053 0.074 Uiso 1 1 calc R U . . .
C40 C 0.43831(19) -0.4991(2) 0.2781(2) 0.0616(11) Uani 1 1 d . . . . .
C39 C 0.41249(19) -0.4671(2) 0.21997(19) 0.0611(11) Uani 1 1 d . . . . .
H39 H 0.441305 -0.445627 0.188423 0.073 Uiso 1 1 calc R U . . .
C38 C 0.34398(19) -0.4666(2) 0.20825(19) 0.0582(10) Uani 1 1 d . . . . .
O2 O 0.14481(12) -1.03324(18) 0.16848(13) 0.0818(9) Uani 1 1 d . . . . .
H2 H 0.146280 -1.039067 0.208889 0.123 Uiso 1 1 d R U . . .
O1 O 0.28905(13) -0.99555(16) -0.01475(13) 0.0738(8) Uani 1 1 d . . . . .
H1 H 0.253180 -0.998939 -0.034815 0.111 Uiso 1 1 d R U . . .
N1 N 0.19112(15) -1.02104(18) 0.28662(15) 0.0600(9) Uani 1 1 d . . . . .
N2 N 0.29731(15) -0.98504(17) 0.30746(15) 0.0558(8) Uani 1 1 d . . . . .
H2A H 0.338299 -0.971718 0.300429 0.067 Uiso 1 1 d R U . . .
C7 C 0.1568(2) -1.0284(2) 0.4068(2) 0.0680(12) Uani 1 1 d . . . . .
H7 H 0.112413 -1.043203 0.398782 0.082 Uiso 1 1 calc R U . . .
C6 C 0.1816(2) -1.0185(2) 0.4712(2) 0.0712(12) Uani 1 1 d . . . . .
H6 H 0.153057 -1.026874 0.506790 0.085 Uiso 1 1 calc R U . . .
C5 C 0.2475(2) -0.9966(2) 0.4838(2) 0.0698(12) Uani 1 1 d . . . . .
H5A H 0.262385 -0.990386 0.527403 0.084 Uiso 1 1 calc R U . . .
C4 C 0.2907(2) -0.9840(2) 0.4330(2) 0.0659(11) Uani 1 1 d . . . . .
H4A H 0.335096 -0.969621 0.441445 0.079 Uiso 1 1 calc R U . . .
C3 C 0.26748(19) -0.9928(2) 0.36847(18) 0.0528(10) Uani 1 1 d . . . . .
C1 C 0.20052(18) -1.0154(2) 0.35553(19) 0.0541(10) Uani 1 1 d . . . . .
C2 C 0.24982(17) -1.0021(2) 0.25963(18) 0.0500(9) Uani 1 1 d . . . . .
C8 C 0.26098(17) -0.9997(2) 0.18948(17) 0.0503(9) Uani 1 1 d . . . . .
C9 C 0.20708(18) -1.0154(2) 0.14560(18) 0.0541(10) Uani 1 1 d . . . . .
C10 C 0.21571(18) -1.0140(2) 0.07756(19) 0.0585(10) Uani 1 1 d . . . . .
H10 H 0.179388 -1.024220 0.049462 0.070 Uiso 1 1 calc R U . . .
C11 C 0.2776(2) -0.9977(2) 0.05118(19) 0.0547(10) Uani 1 1 d . . . . .
C12 C 0.3318(2) -0.9826(2) 0.0939(2) 0.0633(11) Uani 1 1 d . . . . .
H12 H 0.373941 -0.971787 0.076481 0.076 Uiso 1 1 calc R U . . .
C13 C 0.32330(18) -0.9837(2) 0.1609(2) 0.0591(10) Uani 1 1 d . . . . .
H13 H 0.360006 -0.973524 0.188513 0.071 Uiso 1 1 calc R U . . .
N4 N 0.20957(15) -0.73288(18) 0.10845(16) 0.0638(9) Uani 1 1 d . . . . .
C26 C 0.2701(2) -0.6886(2) 0.1376(2) 0.0756(12) Uani 1 1 d . . . . .
H26A H 0.287955 -0.652373 0.104080 0.091 Uiso 1 1 calc R U . . .
H26B H 0.255285 -0.655130 0.174368 0.091 Uiso 1 1 calc R U . . .
C27 C 0.3260(2) -0.7440(3) 0.1621(3) 0.0934(15) Uani 1 1 d . . . . .
H27A H 0.308178 -0.781296 0.194802 0.112 Uiso 1 1 calc R U . . .
H27B H 0.342200 -0.776132 0.125128 0.112 Uiso 1 1 calc R U . . .
C28 C 0.3830(2) -0.6987(3) 0.1920(3) 0.1040(17) Uani 1 1 d . . . . .
H28A H 0.366716 -0.666245 0.228709 0.125 Uiso 1 1 calc R U . . .
H28B H 0.400917 -0.661509 0.159136 0.125 Uiso 1 1 calc R U . . .
C29 C 0.4387(3) -0.7530(4) 0.2167(3) 0.149(3) Uani 1 1 d . . . . .
H29A H 0.453603 -0.787283 0.181218 0.224 Uiso 1 1 calc R U . . .
H29B H 0.422535 -0.786227 0.252390 0.224 Uiso 1 1 calc R U . . .
H29C H 0.475376 -0.720106 0.232396 0.224 Uiso 1 1 calc R U . . .
C14 C 0.2296(2) -0.7831(2) 0.0489(2) 0.0730(12) Uani 1 1 d . . . . .
H14A H 0.190183 -0.811586 0.032597 0.088 Uiso 1 1 calc R U . . .
H14B H 0.261578 -0.823970 0.063671 0.088 Uiso 1 1 calc R U . . .
C15 C 0.2602(2) -0.7370(3) -0.0087(2) 0.0853(14) Uani 1 1 d . . . . .
H15A H 0.227874 -0.697807 -0.025599 0.102 Uiso 1 1 calc R U . . .
H15B H 0.299167 -0.707070 0.007066 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2807(2) -0.7922(3) -0.0638(2) 0.0921(15) Uani 1 1 d . . . . .
H16A H 0.241880 -0.823126 -0.078665 0.110 Uiso 1 1 calc R U . . .
H16B H 0.313688 -0.830607 -0.046987 0.110 Uiso 1 1 calc R U . . .
C17 C 0.3096(3) -0.7479(3) -0.1221(3) 0.125(2) Uani 1 1 d . . . . .
H17A H 0.317611 -0.785893 -0.157435 0.187 Uiso 1 1 calc R U . . .
H17B H 0.351134 -0.722607 -0.109173 0.187 Uiso 1 1 calc R U . . .
H17C H 0.278612 -0.706924 -0.137092 0.187 Uiso 1 1 calc R U . . .
C21 C -0.0203(2) -0.6736(4) 0.0101(3) 0.124(2) Uani 1 1 d . . . . .
H21A H -0.010129 -0.703796 -0.029375 0.186 Uiso 1 1 calc R U . . .
H21B H -0.050154 -0.629646 -0.000792 0.186 Uiso 1 1 calc R U . . .
H21C H -0.041213 -0.709045 0.041668 0.186 Uiso 1 1 calc R U . . .
C20 C 0.0432(3) -0.6400(3) 0.0394(3) 0.1147(18) Uani 1 1 d . . . . .
H20A H 0.062878 -0.602796 0.007671 0.138 Uiso 1 1 calc R U . . .
H20B H 0.032043 -0.608633 0.078635 0.138 Uiso 1 1 calc R U . . .
C19 C 0.0938(2) -0.7015(3) 0.0580(2) 0.0908(15) Uani 1 1 d . . . . .
H19A H 0.104827 -0.732934 0.018846 0.109 Uiso 1 1 calc R U . . .
H19B H 0.074093 -0.738633 0.089844 0.109 Uiso 1 1 calc R U . . .
C18 C 0.1583(2) -0.6678(2) 0.0877(2) 0.0770(13) Uani 1 1 d . . . . .
H18A H 0.147287 -0.635207 0.126234 0.092 Uiso 1 1 calc R U . . .
H18B H 0.178802 -0.631944 0.055424 0.092 Uiso 1 1 calc R U . . .
C22 C 0.1793(2) -0.7898(2) 0.1600(2) 0.0710(12) Uani 1 1 d . . . . .
H22A H 0.141797 -0.818261 0.139461 0.085 Uiso 1 1 calc R U . . .
H22B H 0.212658 -0.830461 0.171825 0.085 Uiso 1 1 calc R U . . .
C23 C 0.1550(2) -0.7504(3) 0.2230(2) 0.0877(14) Uani 1 1 d . . . . .
H23A H 0.191372 -0.719473 0.243093 0.105 Uiso 1 1 calc R U . . .
H23B H 0.118972 -0.712715 0.212387 0.105 Uiso 1 1 calc R U . . .
C24 C 0.1305(3) -0.8119(3) 0.2715(2) 0.1086(17) Uani 1 1 d . . . . .
H24A H 0.166645 -0.849569 0.281785 0.130 Uiso 1 1 calc R U . . .
H24B H 0.094356 -0.842887 0.251071 0.130 Uiso 1 1 calc R U . . .
C25 C 0.1059(3) -0.7751(4) 0.3347(3) 0.137(2) Uani 1 1 d . . . . .
H25A H 0.067771 -0.741153 0.325345 0.206 Uiso 1 1 calc R U . . .
H25B H 0.140946 -0.742870 0.354494 0.206 Uiso 1 1 calc R U . . .
H25C H 0.093267 -0.817702 0.364733 0.206 Uiso 1 1 calc R U . . .
N6 N 0.29934(15) -0.23334(18) -0.11517(15) 0.0593(9) Uani 1 1 d . . . . .
C59 C 0.27909(19) -0.2810(2) -0.05403(18) 0.0613(11) Uani 1 1 d . . . . .
H59A H 0.247960 -0.323308 -0.067843 0.074 Uiso 1 1 calc R U . . .
H59B H 0.318729 -0.307864 -0.036309 0.074 Uiso 1 1 calc R U . . .
C60 C 0.2473(2) -0.2333(2) 0.0013(2) 0.0755(13) Uani 1 1 d . . . . .
H60A H 0.278202 -0.191585 0.016624 0.091 Uiso 1 1 calc R U . . .
H60B H 0.207194 -0.206449 -0.015376 0.091 Uiso 1 1 calc R U . . .
C61 C 0.2291(2) -0.2870(3) 0.0583(2) 0.0877(14) Uani 1 1 d . . . . .
H61A H 0.197762 -0.328092 0.042631 0.105 Uiso 1 1 calc R U . . .
H61B H 0.269244 -0.315046 0.073650 0.105 Uiso 1 1 calc R U . . .
C62 C 0.1988(3) -0.2434(3) 0.1156(2) 0.1117(19) Uani 1 1 d . . . . .
H62A H 0.158126 -0.217076 0.101463 0.168 Uiso 1 1 calc R U . . .
H62B H 0.229764 -0.203337 0.132216 0.168 Uiso 1 1 calc R U . . .
H62C H 0.188953 -0.281840 0.150159 0.168 Uiso 1 1 calc R U . . .
C55 C 0.3491(2) -0.1668(2) -0.0960(2) 0.0688(12) Uani 1 1 d . . . . .
H55A H 0.361845 -0.138016 -0.136048 0.083 Uiso 1 1 calc R U . . .
H55B H 0.326490 -0.128025 -0.067606 0.083 Uiso 1 1 calc R U . . .
C56 C 0.4127(2) -0.1950(3) -0.0607(2) 0.0816(13) Uani 1 1 d . . . . .
H56A H 0.400753 -0.223440 -0.020282 0.098 Uiso 1 1 calc R U . . .
H56B H 0.436316 -0.233101 -0.088918 0.098 Uiso 1 1 calc R U . . .
C57 C 0.4584(2) -0.1256(3) -0.0436(3) 0.1036(16) Uani 1 1 d . . . . .
H57A H 0.434164 -0.086597 -0.016755 0.124 Uiso 1 1 calc R U . . .
H57B H 0.471398 -0.098298 -0.084223 0.124 Uiso 1 1 calc R U . . .
C58 C 0.5207(3) -0.1518(4) -0.0065(3) 0.135(2) Uani 1 1 d . . . . .
H58A H 0.547174 -0.186355 -0.034418 0.202 Uiso 1 1 calc R U . . .
H58B H 0.508287 -0.181157 0.032701 0.202 Uiso 1 1 calc R U . . .
H58C H 0.546403 -0.104580 0.005815 0.202 Uiso 1 1 calc R U . . .
C51 C 0.33033(19) -0.2927(2) -0.16399(19) 0.0627(11) Uani 1 1 d . . . . .
H51A H 0.367864 -0.319451 -0.142118 0.075 Uiso 1 1 calc R U . . .
H51B H 0.297340 -0.334316 -0.174461 0.075 Uiso 1 1 calc R U . . .
C53 C 0.3792(2) -0.3219(3) -0.2737(2) 0.0853(14) Uani 1 1 d . . . . .
H53A H 0.342614 -0.359617 -0.282221 0.102 Uiso 1 1 calc R U . . .
H53B H 0.414604 -0.351863 -0.251215 0.102 Uiso 1 1 calc R U . . .
C54 C 0.4055(3) -0.2917(3) -0.3400(2) 0.1133(18) Uani 1 1 d . . . . .
H54A H 0.419606 -0.337310 -0.366166 0.170 Uiso 1 1 calc R U . . .
H54B H 0.442953 -0.255934 -0.332335 0.170 Uiso 1 1 calc R U . . .
H54C H 0.370662 -0.262653 -0.363148 0.170 Uiso 1 1 calc R U . . .
C52 C 0.3548(2) -0.2566(2) -0.2285(2) 0.0752(13) Uani 1 1 d . . . . .
H52A H 0.318605 -0.226910 -0.249962 0.090 Uiso 1 1 calc R U . . .
H52B H 0.390990 -0.218558 -0.219317 0.090 Uiso 1 1 calc R U . . .
C47 C 0.23773(19) -0.1922(2) -0.1459(2) 0.0673(11) Uani 1 1 d . . . . .
H47A H 0.219900 -0.153823 -0.114022 0.081 Uiso 1 1 calc R U . . .
H47B H 0.251889 -0.161215 -0.184347 0.081 Uiso 1 1 calc R U . . .
C48 C 0.1818(2) -0.2492(3) -0.1673(2) 0.0823(13) Uani 1 1 d . . . . .
H48A H 0.199902 -0.290251 -0.196846 0.099 Uiso 1 1 calc R U . . .
H48B H 0.164549 -0.276898 -0.128538 0.099 Uiso 1 1 calc R U . . .
C49 C 0.1251(2) -0.2054(3) -0.2021(2) 0.0945(15) Uani 1 1 d . . . . .
H49A H 0.107517 -0.163961 -0.172733 0.113 Uiso 1 1 calc R U . . .
H49B H 0.142442 -0.178202 -0.241105 0.113 Uiso 1 1 calc R U . . .
C50 C 0.0690(3) -0.2612(4) -0.2229(3) 0.137(2) Uani 1 1 d . . . . .
H50A H 0.084717 -0.298088 -0.256366 0.205 Uiso 1 1 calc R U . . .
H50B H 0.032494 -0.229553 -0.240481 0.205 Uiso 1 1 calc R U . . .
H50C H 0.054084 -0.291730 -0.185187 0.205 Uiso 1 1 calc R U . . .
F1 F 0.42645(10) -0.96652(15) 0.31048(12) 0.0900(8) Uani 1 1 d . . . . .
F2 F 0.18283(11) -0.98947(16) -0.08272(11) 0.0885(8) Uani 1 1 d . . . . .
O12 O 0.4661(2) -0.6329(2) -0.0896(2) 0.1243(12) Uani 1 1 d G . . . .
H12A H 0.455051 -0.594759 -0.115954 0.186 Uiso 1 1 d G U . . .
H12B H 0.503018 -0.616940 -0.072260 0.186 Uiso 1 1 d G U . . .
O9 O 0.4085(2) -0.4078(3) 0.0371(2) 0.1343(14) Uani 1 1 d G . . . .
H9A H 0.377859 -0.405693 0.065982 0.201 Uiso 1 1 d G U . . .
H9B H 0.409377 -0.467513 0.040279 0.201 Uiso 1 1 d G U . . .
O10 O 0.41416(19) -0.5927(4) 0.0395(2) 0.1496(16) Uani 1 1 d G . . . .
H10A H 0.452604 -0.596995 0.057785 0.224 Uiso 1 1 d G U . . .
H10B H 0.419541 -0.611748 0.000605 0.224 Uiso 1 1 d G U . . .
O11 O 0.54391(19) -0.5914(2) 0.09878(19) 0.1069(11) Uani 1 1 d DG . . . .
H11A H 0.548489 -0.547481 0.120689 0.160 Uiso 1 1 d G U . . .
H11B H 0.564941 -0.576844 0.055771 0.160 Uiso 1 1 d DG U . . .
O6 O 0.0418(2) -1.1053(4) 0.08096(19) 0.1614(18) Uani 1 1 d G . . . .
H6A H 0.000262 -1.115755 0.084481 0.242 Uiso 1 1 d G U . . .
H6B H 0.061525 -1.115109 0.117757 0.242 Uiso 1 1 d G U . . .
O7 O -0.09126(16) -0.8923(2) 0.04747(16) 0.1157(12) Uani 1 1 d . . . . .
H7A H -0.113576 -0.932635 0.061892 0.174 Uiso 1 1 d R U . . .
H7B H -0.092976 -0.897215 0.005492 0.174 Uiso 1 1 d R U . . .
O5 O 0.04507(19) -0.9049(2) 0.0921(2) 0.1170(12) Uani 1 1 d G . . . .
H5B H 0.005600 -0.903439 0.075743 0.175 Uiso 1 1 d G U . . .
H5C H 0.056327 -0.954106 0.099238 0.175 Uiso 1 1 d G U . . .
O8 O 0.09284(19) -0.8816(2) -0.03752(18) 0.1065(11) Uani 1 1 d G . . . .
H8A H 0.080527 -0.897806 0.000522 0.160 Uiso 1 1 d G U . . .
H8B H 0.115881 -0.918678 -0.056035 0.160 Uiso 1 1 d G 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
O4 H4 0.8201 . ?
O4 C38 1.365(4) . ?
O3 H3 0.8187 . ?
O3 C40 1.353(4) . ?
N5 H5 0.8596 . ?
N5 C32 1.393(4) . ?
N5 C31 1.360(4) . ?
N3 C30 1.384(4) . ?
N3 C31 1.337(4) . ?
C33 H33 0.9300 . ?
C33 C34 1.386(6) . ?
C33 C32 1.374(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.370(6) . ?
C35 H35 0.9300 . ?
C35 C36 1.376(5) . ?
C36 H36 0.9300 . ?
C36 C30 1.401(5) . ?
C32 C30 1.388(5) . ?
C31 C37 1.443(5) . ?
C37 C42 1.397(5) . ?
C37 C38 1.401(5) . ?
C42 H42 0.9300 . ?
C42 C41 1.376(5) . ?
C41 H41 0.9300 . ?
C41 C40 1.386(5) . ?
C40 C39 1.378(5) . ?
C39 H39 0.9300 . ?
C39 C38 1.384(5) . ?
O2 H2 0.8200 . ?
O2 C9 1.360(4) . ?
O1 H1 0.8200 . ?
O1 C11 1.350(4) . ?
N1 C1 1.402(4) . ?
N1 C2 1.332(4) . ?
N2 H2A 0.8591 . ?
N2 C3 1.377(4) . ?
N2 C2 1.373(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.395(5) . ?
C7 C1 1.374(5) . ?
C6 H6 0.9300 . ?
C6 C5 1.382(6) . ?
C5 H5A 0.9300 . ?
C5 C4 1.361(5) . ?
C4 H4A 0.9300 . ?
C4 C3 1.383(5) . ?
C3 C1 1.408(5) . ?
C2 C8 1.433(5) . ?
C8 C9 1.409(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(5) . ?
C11 C12 1.398(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(5) . ?
C13 H13 0.9300 . ?
N4 C26 1.521(5) . ?
N4 C14 1.512(5) . ?
N4 C18 1.535(5) . ?
N4 C22 1.526(5) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.517(6) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.482(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.504(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.518(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.492(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.501(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 C20 1.497(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.474(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.516(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.510(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.490(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.496(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N6 C59 1.517(4) . ?
N6 C55 1.523(4) . ?
N6 C51 1.520(4) . ?
N6 C47 1.528(4) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C59 C60 1.508(5) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C60 C61 1.494(5) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C61 C62 1.492(5) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
C55 C56 1.521(5) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C56 C57 1.496(5) . ?
C57 H57A 0.9700 . ?
C57 H57B 0.9700 . ?
C57 C58 1.506(6) . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C51 C52 1.513(5) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C53 C54 1.522(5) . ?
C53 C52 1.490(5) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 C48 1.514(5) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C48 C49 1.507(5) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C49 C50 1.502(6) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
O12 H12A 0.8489 . ?
O12 H12B 0.8517 . ?
O9 H9A 0.8486 . ?
O9 H9B 0.9823 . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8515 . ?
O11 H11A 0.8494 . ?
O11 H11B 0.9954 . ?
O6 H6A 0.8495 . ?
O6 H6B 0.8511 . ?
O7 H7A 0.8503 . ?
O7 H7B 0.8500 . ?
O5 H5B 0.8505 . ?
O5 H5C 0.8496 . ?
O8 H8A 0.8497 . ?
O8 H8B 0.8507 . ?

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
C38 O4 H4 109.7 . . ?
C40 O3 H3 109.5 . . ?
C32 N5 H5 126.8 . . ?
C31 N5 H5 126.8 . . ?
C31 N5 C32 106.5(3) . . ?
C31 N3 C30 105.3(3) . . ?
C34 C33 H33 121.8 . . ?
C32 C33 H33 121.8 . . ?
C32 C33 C34 116.4(4) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 C33 121.5(4) . . ?
C35 C34 H34 119.2 . . ?
C34 C35 H35 118.8 . . ?
C34 C35 C36 122.5(4) . . ?
C36 C35 H35 118.8 . . ?
C35 C36 H36 121.6 . . ?
C35 C36 C30 116.8(4) . . ?
C30 C36 H36 121.6 . . ?
C33 C32 N5 131.1(4) . . ?
C33 C32 C30 122.9(4) . . ?
C30 C32 N5 106.0(3) . . ?
N3 C30 C36 130.3(4) . . ?
N3 C30 C32 109.8(3) . . ?
C32 C30 C36 119.9(4) . . ?
N5 C31 C37 125.0(3) . . ?
N3 C31 N5 112.5(3) . . ?
N3 C31 C37 122.5(3) . . ?
C42 C37 C31 123.0(3) . . ?
C42 C37 C38 117.3(3) . . ?
C38 C37 C31 119.8(3) . . ?
C37 C42 H42 118.9 . . ?
C41 C42 C37 122.1(3) . . ?
C41 C42 H42 118.9 . . ?
C42 C41 H41 120.3 . . ?
C42 C41 C40 119.4(4) . . ?
C40 C41 H41 120.3 . . ?
O3 C40 C41 117.6(4) . . ?
O3 C40 C39 122.4(4) . . ?
C39 C40 C41 120.0(4) . . ?
C40 C39 H39 119.8 . . ?
C40 C39 C38 120.4(4) . . ?
C38 C39 H39 119.8 . . ?
O4 C38 C37 122.0(3) . . ?
O4 C38 C39 117.3(3) . . ?
C39 C38 C37 120.8(4) . . ?
C9 O2 H2 109.7 . . ?
C11 O1 H1 109.1 . . ?
C2 N1 C1 106.2(3) . . ?
C3 N2 H2A 126.2 . . ?
C2 N2 H2A 125.9 . . ?
C2 N2 C3 107.9(3) . . ?
C6 C7 H7 121.3 . . ?
C1 C7 H7 121.3 . . ?
C1 C7 C6 117.3(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 C7 121.9(4) . . ?
C5 C6 H6 119.0 . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5A 119.7 . . ?
C5 C4 H4A 120.6 . . ?
C5 C4 C3 118.9(4) . . ?
C3 C4 H4A 120.6 . . ?
N2 C3 C4 133.3(4) . . ?
N2 C3 C1 106.0(3) . . ?
C4 C3 C1 120.7(4) . . ?
N1 C1 C3 108.5(3) . . ?
C7 C1 N1 130.8(4) . . ?
C7 C1 C3 120.6(4) . . ?
N1 C2 N2 111.3(3) . . ?
N1 C2 C8 123.7(3) . . ?
N2 C2 C8 125.0(3) . . ?
C9 C8 C2 119.3(3) . . ?
C13 C8 C2 123.9(3) . . ?
C13 C8 C9 116.8(3) . . ?
O2 C9 C8 121.3(3) . . ?
O2 C9 C10 117.5(3) . . ?
C10 C9 C8 121.1(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
O1 C11 C10 123.2(4) . . ?
O1 C11 C12 117.6(3) . . ?
C10 C11 C12 119.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.9 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.0(4) . . ?
C12 C13 H13 119.0 . . ?
C26 N4 C18 107.3(3) . . ?
C26 N4 C22 110.3(3) . . ?
C14 N4 C26 110.6(3) . . ?
C14 N4 C18 110.1(3) . . ?
C14 N4 C22 108.4(3) . . ?
C22 N4 C18 110.2(3) . . ?
N4 C26 H26A 108.6 . . ?
N4 C26 H26B 108.6 . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 N4 114.6(3) . . ?
C27 C26 H26A 108.6 . . ?
C27 C26 H26B 108.6 . . ?
C26 C27 H27A 109.0 . . ?
C26 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 C26 113.0(4) . . ?
C28 C27 H27A 109.0 . . ?
C28 C27 H27B 109.0 . . ?
C27 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
C27 C28 C29 113.4(5) . . ?
H28A C28 H28B 107.7 . . ?
C29 C28 H28A 108.9 . . ?
C29 C28 H28B 108.9 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C14 H14A 108.1 . . ?
N4 C14 H14B 108.1 . . ?
N4 C14 C15 116.6(3) . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.4(4) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C15 C16 C17 113.5(4) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
H20A C20 H20B 107.5 . . ?
C19 C20 C21 115.0(4) . . ?
C19 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C20 C19 C18 115.2(4) . . ?
H19A C19 H19B 107.5 . . ?
C18 C19 H19A 108.5 . . ?
C18 C19 H19B 108.5 . . ?
N4 C18 H18A 108.6 . . ?
N4 C18 H18B 108.6 . . ?
C19 C18 N4 114.4(3) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
N4 C22 H22A 108.2 . . ?
N4 C22 H22B 108.2 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 N4 116.2(3) . . ?
C23 C22 H22A 108.2 . . ?
C23 C22 H22B 108.2 . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22 111.8(4) . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.3(4) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C59 N6 C55 110.0(3) . . ?
C59 N6 C51 108.0(3) . . ?
C59 N6 C47 109.8(3) . . ?
C55 N6 C47 107.8(3) . . ?
C51 N6 C55 110.8(3) . . ?
C51 N6 C47 110.5(3) . . ?
N6 C59 H59A 108.1 . . ?
N6 C59 H59B 108.1 . . ?
H59A C59 H59B 107.3 . . ?
C60 C59 N6 116.8(3) . . ?
C60 C59 H59A 108.1 . . ?
C60 C59 H59B 108.1 . . ?
C59 C60 H60A 109.3 . . ?
C59 C60 H60B 109.3 . . ?
H60A C60 H60B 108.0 . . ?
C61 C60 C59 111.7(3) . . ?
C61 C60 H60A 109.3 . . ?
C61 C60 H60B 109.3 . . ?
C60 C61 H61A 108.6 . . ?
C60 C61 H61B 108.6 . . ?
H61A C61 H61B 107.6 . . ?
C62 C61 C60 114.5(4) . . ?
C62 C61 H61A 108.6 . . ?
C62 C61 H61B 108.6 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
C61 C62 H62C 109.5 . . ?
H62A C62 H62B 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
N6 C55 H55A 108.3 . . ?
N6 C55 H55B 108.3 . . ?
H55A C55 H55B 107.4 . . ?
C56 C55 N6 116.0(3) . . ?
C56 C55 H55A 108.3 . . ?
C56 C55 H55B 108.3 . . ?
C55 C56 H56A 109.2 . . ?
C55 C56 H56B 109.2 . . ?
H56A C56 H56B 107.9 . . ?
C57 C56 C55 112.3(4) . . ?
C57 C56 H56A 109.2 . . ?
C57 C56 H56B 109.2 . . ?
C56 C57 H57A 108.9 . . ?
C56 C57 H57B 108.9 . . ?
C56 C57 C58 113.2(4) . . ?
H57A C57 H57B 107.8 . . ?
C58 C57 H57A 108.9 . . ?
C58 C57 H57B 108.9 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
N6 C51 H51A 108.2 . . ?
N6 C51 H51B 108.2 . . ?
H51A C51 H51B 107.4 . . ?
C52 C51 N6 116.2(3) . . ?
C52 C51 H51A 108.2 . . ?
C52 C51 H51B 108.2 . . ?
H53A C53 H53B 107.5 . . ?
C54 C53 H53A 108.6 . . ?
C54 C53 H53B 108.6 . . ?
C52 C53 H53A 108.6 . . ?
C52 C53 H53B 108.6 . . ?
C52 C53 C54 114.8(4) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C53 C52 C51 110.7(3) . . ?
C53 C52 H52A 109.5 . . ?
C53 C52 H52B 109.5 . . ?
H52A C52 H52B 108.1 . . ?
N6 C47 H47A 108.4 . . ?
N6 C47 H47B 108.4 . . ?
H47A C47 H47B 107.5 . . ?
C48 C47 N6 115.4(3) . . ?
C48 C47 H47A 108.4 . . ?
C48 C47 H47B 108.4 . . ?
C47 C48 H48A 109.1 . . ?
C47 C48 H48B 109.1 . . ?
H48A C48 H48B 107.8 . . ?
C49 C48 C47 112.6(4) . . ?
C49 C48 H48A 109.1 . . ?
C49 C48 H48B 109.1 . . ?
C48 C49 H49A 109.0 . . ?
C48 C49 H49B 109.0 . . ?
H49A C49 H49B 107.8 . . ?
C50 C49 C48 113.1(4) . . ?
C50 C49 H49A 109.0 . . ?
C50 C49 H49B 109.0 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
H12A O12 H12B 104.4 . . ?
H9A O9 H9B 90.5 . . ?
H10A O10 H10B 104.3 . . ?
H11A O11 H11B 101.8 . . ?
H6A O6 H6B 109.4 . . ?
H7A O7 H7B 104.5 . . ?
H5B O5 H5C 109.5 . . ?
H8A O8 H8B 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
O3 C40 C39 C38 178.6(3) . . . . ?
N5 C32 C30 N3 0.5(4) . . . . ?
N5 C32 C30 C36 -176.5(3) . . . . ?
N5 C31 C37 C42 4.0(5) . . . . ?
N5 C31 C37 C38 -175.7(3) . . . . ?
N3 C31 C37 C42 -175.2(3) . . . . ?
N3 C31 C37 C38 5.0(5) . . . . ?
C33 C34 C35 C36 0.1(8) . . . . ?
C33 C32 C30 N3 179.8(4) . . . . ?
C33 C32 C30 C36 2.8(6) . . . . ?
C34 C33 C32 N5 177.2(4) . . . . ?
C34 C33 C32 C30 -1.8(6) . . . . ?
C34 C35 C36 C30 0.8(7) . . . . ?
C35 C36 C30 N3 -178.4(4) . . . . ?
C35 C36 C30 C32 -2.1(6) . . . . ?
C32 N5 C31 N3 -1.0(4) . . . . ?
C32 N5 C31 C37 179.7(3) . . . . ?
C32 C33 C34 C35 0.4(7) . . . . ?
C30 N3 C31 N5 1.3(4) . . . . ?
C30 N3 C31 C37 -179.4(3) . . . . ?
C31 N5 C32 C33 -178.9(4) . . . . ?
C31 N5 C32 C30 0.3(4) . . . . ?
C31 N3 C30 C36 175.5(4) . . . . ?
C31 N3 C30 C32 -1.1(4) . . . . ?
C31 C37 C42 C41 179.6(3) . . . . ?
C31 C37 C38 O4 0.4(5) . . . . ?
C31 C37 C38 C39 179.0(3) . . . . ?
C37 C42 C41 C40 1.1(6) . . . . ?
C42 C37 C38 O4 -179.3(3) . . . . ?
C42 C37 C38 C39 -0.8(5) . . . . ?
C42 C41 C40 O3 -179.9(3) . . . . ?
C42 C41 C40 C39 -0.1(6) . . . . ?
C41 C40 C39 C38 -1.2(6) . . . . ?
C40 C39 C38 O4 -179.7(3) . . . . ?
C40 C39 C38 C37 1.7(6) . . . . ?
C38 C37 C42 C41 -0.6(5) . . . . ?
O2 C9 C10 C11 -179.0(3) . . . . ?
O1 C11 C12 C13 179.8(3) . . . . ?
N1 C2 C8 C9 2.2(5) . . . . ?
N1 C2 C8 C13 -176.8(3) . . . . ?
N2 C3 C1 N1 0.1(4) . . . . ?
N2 C3 C1 C7 179.8(3) . . . . ?
N2 C2 C8 C9 -177.5(3) . . . . ?
N2 C2 C8 C13 3.5(6) . . . . ?
C7 C6 C5 C4 -0.1(6) . . . . ?
C6 C7 C1 N1 179.4(4) . . . . ?
C6 C7 C1 C3 -0.2(6) . . . . ?
C6 C5 C4 C3 0.5(6) . . . . ?
C5 C4 C3 N2 -179.7(4) . . . . ?
C5 C4 C3 C1 -0.7(6) . . . . ?
C4 C3 C1 N1 -179.1(3) . . . . ?
C4 C3 C1 C7 0.5(5) . . . . ?
C3 N2 C2 N1 -0.5(4) . . . . ?
C3 N2 C2 C8 179.3(3) . . . . ?
C1 N1 C2 N2 0.6(4) . . . . ?
C1 N1 C2 C8 -179.2(3) . . . . ?
C1 C7 C6 C5 -0.1(6) . . . . ?
C2 N1 C1 C7 180.0(4) . . . . ?
C2 N1 C1 C3 -0.4(4) . . . . ?
C2 N2 C3 C4 179.3(4) . . . . ?
C2 N2 C3 C1 0.2(4) . . . . ?
C2 C8 C9 O2 -0.4(5) . . . . ?
C2 C8 C9 C10 -179.8(3) . . . . ?
C2 C8 C13 C12 179.5(4) . . . . ?
C8 C9 C10 C11 0.4(6) . . . . ?
C9 C8 C13 C12 0.5(5) . . . . ?
C9 C10 C11 O1 180.0(3) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C8 0.0(6) . . . . ?
C13 C8 C9 O2 178.7(3) . . . . ?
C13 C8 C9 C10 -0.7(5) . . . . ?
N4 C26 C27 C28 -178.2(4) . . . . ?
N4 C14 C15 C16 177.8(3) . . . . ?
N4 C22 C23 C24 -176.3(4) . . . . ?
C26 N4 C14 C15 -59.7(4) . . . . ?
C26 N4 C18 C19 -179.3(4) . . . . ?
C26 N4 C22 C23 59.7(4) . . . . ?
C26 C27 C28 C29 179.7(4) . . . . ?
C14 N4 C26 C27 -60.9(5) . . . . ?
C14 N4 C18 C19 60.3(5) . . . . ?
C14 N4 C22 C23 -179.0(3) . . . . ?
C14 C15 C16 C17 178.7(4) . . . . ?
C21 C20 C19 C18 179.9(4) . . . . ?
C20 C19 C18 N4 178.4(4) . . . . ?
C18 N4 C26 C27 179.1(4) . . . . ?
C18 N4 C14 C15 58.7(4) . . . . ?
C18 N4 C22 C23 -58.5(4) . . . . ?
C22 N4 C26 C27 59.1(5) . . . . ?
C22 N4 C14 C15 179.2(3) . . . . ?
C22 N4 C18 C19 -59.2(5) . . . . ?
C22 C23 C24 C25 -179.9(4) . . . . ?
N6 C59 C60 C61 179.5(3) . . . . ?
N6 C55 C56 C57 -179.8(4) . . . . ?
N6 C51 C52 C53 -175.7(3) . . . . ?
N6 C47 C48 C49 -175.4(3) . . . . ?
C59 N6 C55 C56 57.0(4) . . . . ?
C59 N6 C51 C52 -179.2(3) . . . . ?
C59 N6 C47 C48 -59.3(4) . . . . ?
C59 C60 C61 C62 178.7(4) . . . . ?
C55 N6 C59 C60 58.7(4) . . . . ?
C55 N6 C51 C52 -58.7(4) . . . . ?
C55 N6 C47 C48 -179.1(3) . . . . ?
C55 C56 C57 C58 178.1(4) . . . . ?
C51 N6 C59 C60 179.7(3) . . . . ?
C51 N6 C55 C56 -62.3(4) . . . . ?
C51 N6 C47 C48 59.6(4) . . . . ?
C54 C53 C52 C51 -179.5(4) . . . . ?
C47 N6 C59 C60 -59.7(4) . . . . ?
C47 N6 C55 C56 176.6(3) . . . . ?
C47 N6 C51 C52 60.7(4) . . . . ?
C47 C48 C49 C50 -179.4(4) . . . . ?

_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_bihqtbaf_pra_0m
_database_code_depnum_ccdc_archive 'CCDC 2387453'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H34.55 N, C16 H11 N3 O, F, 2(H2 O)'
_chemical_formula_sum            'C32 H49.55 F N4 O3'
_chemical_formula_weight         557.30

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'
F F 0.0171 0.0103 '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                   8.2214(14)
_cell_length_b                   17.687(3)
_cell_length_c                   23.149(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.908(5)
_cell_angle_gamma                90
_cell_volume                     3334.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    3585
_cell_measurement_theta_min      0.985
_cell_measurement_theta_max      0.987

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             1210
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299.00
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44154
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5837
_reflns_number_gt                3585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          '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)+(0.1099P)²+0.1279P] 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     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.043(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5837
_refine_ls_number_parameters     451
_refine_ls_number_restraints     211
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1977
_refine_ls_wR_factor_gt          0.1739
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5179(2) 0.68175(7) 0.54459(6) 0.0990(5) Uani 1 1 d . . . . .
O1 O -0.1337(2) 1.10820(8) 0.87213(6) 0.0792(5) Uani 1 1 d . . . . .
H1 H -0.104529 1.128380 0.903755 0.119 Uiso 1 1 calc R U . . .
O3 O 0.5968(3) 0.78505(11) 0.63047(10) 0.0988(6) Uani 1 1 d D . . . .
N1 N -0.3255(2) 0.74662(10) 0.86685(8) 0.0696(5) Uani 1 1 d . . . . .
O2 O -0.0758(3) 1.18958(11) 0.76367(8) 0.0988(6) Uani 1 1 d G . . . .
H2A H -0.115424 1.146674 0.770681 0.148 Uiso 1 1 d G U . . .
H2B H -0.116816 1.199153 0.728639 0.148 Uiso 1 1 d G U . . .
N2 N -0.1564(2) 0.76207(9) 0.95072(7) 0.0663(5) Uani 1 1 d . . . . .
H2 H -0.090713 0.783905 0.977773 0.080 Uiso 1 1 calc R U . . .
N3 N -0.2111(3) 1.02613(11) 0.77646(8) 0.0778(6) Uani 1 1 d . . . . .
C2 C -0.2325(3) 0.79529(12) 0.90082(9) 0.0615(5) Uani 1 1 d . . . . .
C11 C -0.1601(3) 1.03451(11) 0.88014(9) 0.0602(5) Uani 1 1 d . . . . .
C13 C -0.2241(2) 0.91059(11) 0.83403(8) 0.0587(5) Uani 1 1 d . . . . .
C12 C -0.1993(2) 0.98940(11) 0.82931(8) 0.0603(5) Uani 1 1 d . . . . .
C10 C -0.1506(3) 1.00102(12) 0.93352(9) 0.0650(6) Uani 1 1 d . . . . .
H10 H -0.127698 1.030319 0.967018 0.078 Uiso 1 1 calc R U . . .
C8 C -0.2106(3) 0.87660(11) 0.89101(8) 0.0588(5) Uani 1 1 d . . . . .
C1 C -0.3090(3) 0.67879(12) 0.89753(10) 0.0701(6) Uani 1 1 d . . . . .
N4 N 0.0945(3) 0.70092(15) 0.64585(9) 0.0928(7) Uani 1 1 d D . . . .
C9 C -0.1748(3) 0.92321(12) 0.93858(9) 0.0649(6) Uani 1 1 d . . . . .
H9 H -0.166361 0.902097 0.975671 0.078 Uiso 1 1 calc R U . . .
C14 C -0.2594(3) 0.87022(13) 0.78100(9) 0.0735(6) Uani 1 1 d . . . . .
H14 H -0.274840 0.818149 0.781579 0.088 Uiso 1 1 calc R U . . .
C3 C -0.2036(3) 0.68761(11) 0.94980(10) 0.0675(6) Uani 1 1 d . . . . .
C7 C -0.3824(4) 0.60872(14) 0.88396(12) 0.0886(8) Uani 1 1 d . . . . .
H7 H -0.455023 0.601542 0.849898 0.106 Uiso 1 1 calc R U . . .
C15 C -0.2706(3) 0.90732(15) 0.72937(10) 0.0857(7) Uani 1 1 d . . . . .
H15 H -0.294467 0.881032 0.694437 0.103 Uiso 1 1 calc R U . . .
C16 C -0.2459(4) 0.98534(15) 0.72917(10) 0.0892(8) Uani 1 1 d . . . . .
H16 H -0.254633 1.009833 0.693323 0.107 Uiso 1 1 calc R U . . .
C29 C 0.025(3) 0.6972(18) 0.7044(7) 0.099(6) Uani 0.306(10) 1 d D . P A 1
H29A H 0.010997 0.748253 0.718278 0.119 Uiso 0.306(10) 1 calc R U P A 1
H29B H -0.083052 0.673773 0.697946 0.119 Uiso 0.306(10) 1 calc R U P A 1
C4 C -0.1647(4) 0.62899(14) 0.98872(11) 0.0871(8) Uani 1 1 d . . . . .
H4 H -0.093647 0.635851 1.023213 0.104 Uiso 1 1 calc R U . . .
C6 C -0.3433(4) 0.55091(16) 0.92275(14) 0.1071(10) Uani 1 1 d . . . . .
H6 H -0.390502 0.503687 0.914420 0.129 Uiso 1 1 calc R U . . .
C21 C -0.0400(3) 0.71656(18) 0.59593(11) 0.0942(8) Uani 1 1 d . . . . .
H21A H -0.101886 0.760150 0.606066 0.113 Uiso 1 1 calc R U . . .
H21B H -0.114403 0.673710 0.592065 0.113 Uiso 1 1 calc R U . . .
C17 C 0.1996(3) 0.63490(19) 0.63253(13) 0.1005(9) Uani 1 1 d . . . . .
H17A H 0.253898 0.648124 0.599288 0.121 Uiso 1 1 calc R U . . .
H17B H 0.284273 0.627353 0.665558 0.121 Uiso 1 1 calc R U . . .
C22 C 0.0154(4) 0.7313(2) 0.53681(13) 0.1096(10) Uani 1 1 d . . . . .
H22A H 0.055515 0.684589 0.521891 0.132 Uiso 1 1 calc R U . . .
H22B H 0.104825 0.767474 0.541278 0.132 Uiso 1 1 calc R U . . .
C5 C -0.2358(4) 0.56015(15) 0.97408(14) 0.1048(10) Uani 1 1 d . . . . .
H5 H -0.211648 0.519089 0.998880 0.126 Uiso 1 1 calc R U . . .
C23 C -0.1257(4) 0.7618(2) 0.49352(14) 0.1206(11) Uani 1 1 d . . . . .
H23A H -0.094286 0.760385 0.454649 0.145 Uiso 1 1 calc R U . . .
H23B H -0.220462 0.729198 0.493712 0.145 Uiso 1 1 calc R U . . .
C18 C 0.1113(4) 0.5618(2) 0.61965(16) 0.1166(10) Uani 1 1 d . . . . .
H18A H 0.026452 0.567899 0.586464 0.140 Uiso 1 1 calc R U . . .
H18B H 0.059229 0.546495 0.652942 0.140 Uiso 1 1 calc R U . . .
C30 C 0.134(4) 0.653(2) 0.7520(7) 0.117(6) Uani 0.306(10) 1 d D . P A 1
H30A H 0.133564 0.599542 0.741244 0.140 Uiso 0.306(10) 1 calc R U P A 1
H30B H 0.246310 0.670733 0.754452 0.140 Uiso 0.306(10) 1 calc R U P A 1
C24 C -0.1735(6) 0.8423(3) 0.5071(2) 0.1562(15) Uani 1 1 d . . . . .
H24A H -0.260641 0.859020 0.477973 0.234 Uiso 1 1 calc R U . . .
H24B H -0.080210 0.874904 0.507046 0.234 Uiso 1 1 calc R U . . .
H24C H -0.209874 0.843689 0.544720 0.234 Uiso 1 1 calc R U . . .
C19 C 0.2312(5) 0.5019(2) 0.6065(2) 0.1419(13) Uani 1 1 d D . . . .
H19A H 0.283487 0.518387 0.573560 0.170 Uiso 1 1 calc R U . . .
H19B H 0.316103 0.497051 0.639780 0.170 Uiso 1 1 calc R U . . .
C31 C 0.077(3) 0.6603(11) 0.8112(8) 0.142(8) Uani 0.306(10) 1 d D . P A 1
H31A H -0.039571 0.649362 0.808247 0.170 Uiso 0.306(10) 1 calc R U P A 1
H31B H 0.135795 0.625183 0.838681 0.170 Uiso 0.306(10) 1 calc R U P A 1
C20 C 0.1579(7) 0.4278(3) 0.5932(3) 0.231(3) Uani 1 1 d D . . . .
H20A H 0.060730 0.433195 0.565346 0.346 Uiso 1 1 calc R U . . .
H20B H 0.129726 0.405376 0.628260 0.346 Uiso 1 1 calc R U . . .
H20C H 0.235118 0.395904 0.577202 0.346 Uiso 1 1 calc R U . . .
C34 C 0.1100(19) 0.7401(10) 0.8315(7) 0.163(7) Uani 0.306(10) 1 d D . P A 1
H34A H 0.224330 0.745611 0.846246 0.245 Uiso 0.306(10) 1 calc R U P A 1
H34B H 0.045096 0.751665 0.861767 0.245 Uiso 0.306(10) 1 calc R U P A 1
H34C H 0.081762 0.774141 0.799333 0.245 Uiso 0.306(10) 1 calc R U P A 1
C25 C 0.218(2) 0.7658(8) 0.6528(12) 0.104(4) Uani 0.517(13) 1 d D U P A 1
H25A H 0.267410 0.771371 0.617249 0.125 Uiso 0.517(13) 1 calc R U P A 1
H25B H 0.305390 0.754412 0.684362 0.125 Uiso 0.517(13) 1 calc R U P A 1
C36 C 0.1334(16) 0.8397(7) 0.6660(7) 0.124(4) Uani 0.517(13) 1 d D U P A 1
H36A H 0.059005 0.856245 0.632174 0.148 Uiso 0.517(13) 1 calc R U P A 1
H36B H 0.071273 0.832896 0.698339 0.148 Uiso 0.517(13) 1 calc R U P A 1
C35 C 0.2675(15) 0.8967(6) 0.6813(5) 0.156(5) Uani 0.517(13) 1 d D U P A 1
H35A H 0.361373 0.871908 0.703412 0.187 Uiso 0.517(13) 1 calc R U P A 1
H35B H 0.301681 0.916116 0.645671 0.187 Uiso 0.517(13) 1 calc R U P A 1
C28 C 0.2163(18) 0.9597(8) 0.7154(7) 0.261(9) Uani 0.517(13) 1 d D U P A 1
H28A H 0.305851 0.994516 0.724057 0.391 Uiso 0.517(13) 1 calc R U P A 1
H28B H 0.124825 0.985077 0.693326 0.391 Uiso 0.517(13) 1 calc R U P A 1
H28C H 0.184508 0.940876 0.751059 0.391 Uiso 0.517(13) 1 calc R U P A 1
H3A H 0.577(4) 0.7517(14) 0.6021(9) 0.119(11) Uiso 1 1 d D . . . .
H3B H 0.592(5) 0.7546(16) 0.6600(9) 0.139(14) Uiso 1 1 d D . . . .
C5A C 0.294(3) 0.9485(12) 0.6512(9) 0.332(12) Uani 0.483(13) 1 d D . P A 2
C27 C 0.251(2) 0.9064(11) 0.7046(9) 0.252(10) Uani 0.483(13) 1 d D . P A 2
H27A H 0.203040 0.939975 0.730802 0.303 Uiso 0.483(13) 1 calc R U P A 2
H27B H 0.346349 0.881632 0.725684 0.303 Uiso 0.483(13) 1 calc R U P A 2
C26 C 0.123(3) 0.8478(10) 0.6756(13) 0.219(10) Uani 0.483(13) 1 d D . P A 2
H26A H 0.041300 0.838879 0.701363 0.263 Uiso 0.483(13) 1 calc R U P A 2
H26B H 0.066833 0.868992 0.639567 0.263 Uiso 0.483(13) 1 calc R U P A 2
C2A C 0.200(2) 0.7734(9) 0.6624(14) 0.119(5) Uani 0.483(13) 1 d D . P A 2
H2AA H 0.277755 0.760550 0.696329 0.143 Uiso 0.483(13) 1 calc R U P A 2
H2AB H 0.263108 0.782581 0.630743 0.143 Uiso 0.483(13) 1 calc R U P A 2
C32 C 0.1234(9) 0.6494(7) 0.8606(3) 0.235(7) Uani 0.694(10) 1 d D . P A 2
H32A H 0.054488 0.644929 0.890697 0.352 Uiso 0.694(10) 1 calc R U P A 2
H32B H 0.183112 0.603181 0.857976 0.352 Uiso 0.694(10) 1 calc R U P A 2
H32C H 0.199275 0.690337 0.869693 0.352 Uiso 0.694(10) 1 calc R U P A 2
C0 C 0.0211(15) 0.6644(6) 0.8045(3) 0.142(4) Uani 0.694(10) 1 d D . P A 2
H0A H -0.040810 0.710541 0.807749 0.171 Uiso 0.694(10) 1 calc R U P A 2
H0B H -0.056966 0.623419 0.796036 0.171 Uiso 0.694(10) 1 calc R U P A 2
C33 C 0.1184(16) 0.6722(10) 0.7550(4) 0.138(5) Uani 0.694(10) 1 d D . P A 2
H33A H 0.187019 0.627939 0.753149 0.165 Uiso 0.694(10) 1 calc R U P A 2
H33B H 0.189332 0.716131 0.761203 0.165 Uiso 0.694(10) 1 calc R U P A 2
C37 C 0.0032(10) 0.6809(7) 0.6972(3) 0.084(2) Uani 0.694(10) 1 d D . P A 2
H37A H -0.056251 0.633985 0.688587 0.100 Uiso 0.694(10) 1 calc R U P A 2
H37B H -0.076570 0.720199 0.701524 0.100 Uiso 0.694(10) 1 calc R U P A 2


_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
O1 C11 1.338(2) . ?
O1 H1 0.8200 . ?
O3 H3A 0.881(17) . ?
O3 H3B 0.874(18) . ?
N1 C2 1.333(3) . ?
N1 C1 1.391(3) . ?
O2 H2A 0.8502 . ?
O2 H2B 0.8513 . ?
N2 C2 1.369(3) . ?
N2 C3 1.372(3) . ?
N2 H2 0.8600 . ?
N3 C16 1.310(3) . ?
N3 C12 1.377(3) . ?
C2 C8 1.471(3) . ?
C11 C10 1.363(3) . ?
C11 C12 1.421(3) . ?
C13 C12 1.415(3) . ?
C13 C14 1.415(3) . ?
C13 C8 1.440(3) . ?
C10 C9 1.398(3) . ?
C10 H10 0.9300 . ?
C8 C9 1.375(3) . ?
C1 C7 1.395(3) . ?
C1 C3 1.397(3) . ?
N4 C17 1.509(4) . ?
N4 C21 1.511(3) . ?
N4 C25 1.528(10) . ?
N4 C37 1.531(7) . ?
N4 C29 1.545(14) . ?
N4 C2A 1.564(11) . ?
C9 H9 0.9300 . ?
C14 C15 1.356(3) . ?
C14 H14 0.9300 . ?
C3 C4 1.382(3) . ?
C7 C6 1.369(4) . ?
C7 H7 0.9300 . ?
C15 C16 1.395(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C29 C30 1.541(16) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.390(4) . ?
C6 H6 0.9300 . ?
C21 C22 1.523(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C17 C18 1.493(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C22 C23 1.524(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C5 H5 0.9300 . ?
C23 C24 1.520(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C18 C19 1.506(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C30 C31 1.515(14) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C19 C20 1.457(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C31 C34 1.500(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C25 C36 1.534(10) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C36 C35 1.499(9) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C35 C28 1.460(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C5A C27 1.525(15) . ?
C27 C26 1.562(13) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C26 C2A 1.510(12) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C2A H2AA 0.9700 . ?
C2A H2AB 0.9700 . ?
C32 C0 1.471(10) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C0 C33 1.491(9) . ?
C0 H0A 0.9700 . ?
C0 H0B 0.9700 . ?
C33 C37 1.537(9) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?

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
C11 O1 H1 109.5 . . ?
H3A O3 H3B 98(2) . . ?
C2 N1 C1 104.37(18) . . ?
H2A O2 H2B 104.3 . . ?
C2 N2 C3 107.65(17) . . ?
C2 N2 H2 126.2 . . ?
C3 N2 H2 126.2 . . ?
C16 N3 C12 117.6(2) . . ?
N1 C2 N2 112.29(18) . . ?
N1 C2 C8 127.78(19) . . ?
N2 C2 C8 119.90(17) . . ?
O1 C11 C10 123.96(18) . . ?
O1 C11 C12 117.05(17) . . ?
C10 C11 C12 118.99(19) . . ?
C12 C13 C14 116.39(18) . . ?
C12 C13 C8 119.22(17) . . ?
C14 C13 C8 124.38(19) . . ?
N3 C12 C13 122.69(18) . . ?
N3 C12 C11 116.79(18) . . ?
C13 C12 C11 120.51(17) . . ?
C11 C10 C9 120.85(18) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C9 C8 C13 117.68(18) . . ?
C9 C8 C2 118.68(18) . . ?
C13 C8 C2 123.64(17) . . ?
N1 C1 C7 130.0(2) . . ?
N1 C1 C3 110.55(18) . . ?
C7 C1 C3 119.5(2) . . ?
C17 N4 C21 111.4(2) . . ?
C17 N4 C25 102.1(7) . . ?
C21 N4 C25 110.5(11) . . ?
C17 N4 C37 109.6(4) . . ?
C21 N4 C37 104.5(4) . . ?
C17 N4 C29 116.0(11) . . ?
C21 N4 C29 111.0(9) . . ?
C25 N4 C29 105.2(15) . . ?
C17 N4 C2A 111.8(8) . . ?
C21 N4 C2A 111.1(12) . . ?
C37 N4 C2A 108.2(12) . . ?
C8 C9 C10 122.72(18) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N2 C3 C4 132.1(2) . . ?
N2 C3 C1 105.14(18) . . ?
C4 C3 C1 122.8(2) . . ?
C6 C7 C1 117.4(3) . . ?
C6 C7 H7 121.3 . . ?
C1 C7 H7 121.3 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N3 C16 C15 123.9(2) . . ?
N3 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C30 C29 N4 113.4(15) . . ?
C30 C29 H29A 108.9 . . ?
N4 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
N4 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
C5 C4 C3 116.9(3) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
C7 C6 C5 122.5(3) . . ?
C7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
N4 C21 C22 116.1(2) . . ?
N4 C21 H21A 108.3 . . ?
C22 C21 H21A 108.3 . . ?
N4 C21 H21B 108.3 . . ?
C22 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C18 C17 N4 115.8(2) . . ?
C18 C17 H17A 108.3 . . ?
N4 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N4 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C21 C22 C23 110.9(2) . . ?
C21 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.0 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C24 C23 C22 113.0(3) . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C17 C18 C19 109.6(3) . . ?
C17 C18 H18A 109.7 . . ?
C19 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C19 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C31 C30 C29 112.0(16) . . ?
C31 C30 H30A 109.2 . . ?
C29 C30 H30A 109.2 . . ?
C31 C30 H30B 109.2 . . ?
C29 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C19 C18 114.3(4) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C34 C31 C30 107.6(18) . . ?
C34 C31 H31A 110.2 . . ?
C30 C31 H31A 110.2 . . ?
C34 C31 H31B 110.2 . . ?
C30 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C25 C36 110.2(9) . . ?
N4 C25 H25A 109.6 . . ?
C36 C25 H25A 109.6 . . ?
N4 C25 H25B 109.6 . . ?
C36 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C35 C36 C25 106.2(8) . . ?
C35 C36 H36A 110.5 . . ?
C25 C36 H36A 110.5 . . ?
C35 C36 H36B 110.5 . . ?
C25 C36 H36B 110.5 . . ?
H36A C36 H36B 108.7 . . ?
C28 C35 C36 112.5(10) . . ?
C28 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
C28 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C28 H28A 109.5 . . ?
C35 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C35 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C5A C27 C26 101.1(15) . . ?
C5A C27 H27A 111.5 . . ?
C26 C27 H27A 111.5 . . ?
C5A C27 H27B 111.5 . . ?
C26 C27 H27B 111.5 . . ?
H27A C27 H27B 109.4 . . ?
C2A C26 C27 112.9(14) . . ?
C2A C26 H26A 109.0 . . ?
C27 C26 H26A 109.0 . . ?
C2A C26 H26B 109.0 . . ?
C27 C26 H26B 109.0 . . ?
H26A C26 H26B 107.8 . . ?
C26 C2A N4 122.1(12) . . ?
C26 C2A H2AA 106.8 . . ?
N4 C2A H2AA 106.8 . . ?
C26 C2A H2AB 106.8 . . ?
N4 C2A H2AB 106.8 . . ?
H2AA C2A H2AB 106.7 . . ?
C0 C32 H32A 109.5 . . ?
C0 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C0 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C32 C0 C33 113.2(8) . . ?
C32 C0 H0A 108.9 . . ?
C33 C0 H0A 108.9 . . ?
C32 C0 H0B 108.9 . . ?
C33 C0 H0B 108.9 . . ?
H0A C0 H0B 107.8 . . ?
C0 C33 C37 110.3(8) . . ?
C0 C33 H33A 109.6 . . ?
C37 C33 H33A 109.6 . . ?
C0 C33 H33B 109.6 . . ?
C37 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N4 C37 C33 112.9(7) . . ?
N4 C37 H37A 109.0 . . ?
C33 C37 H37A 109.0 . . ?
N4 C37 H37B 109.0 . . ?
C33 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?

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
C1 N1 C2 N2 0.9(2) . . . . ?
C1 N1 C2 C8 -176.9(2) . . . . ?
C3 N2 C2 N1 -0.8(2) . . . . ?
C3 N2 C2 C8 177.25(18) . . . . ?
C16 N3 C12 C13 -0.4(3) . . . . ?
C16 N3 C12 C11 179.5(2) . . . . ?
C14 C13 C12 N3 1.2(3) . . . . ?
C8 C13 C12 N3 -179.59(19) . . . . ?
C14 C13 C12 C11 -178.8(2) . . . . ?
C8 C13 C12 C11 0.5(3) . . . . ?
O1 C11 C12 N3 -1.8(3) . . . . ?
C10 C11 C12 N3 178.6(2) . . . . ?
O1 C11 C12 C13 178.13(19) . . . . ?
C10 C11 C12 C13 -1.5(3) . . . . ?
O1 C11 C10 C9 -178.0(2) . . . . ?
C12 C11 C10 C9 1.6(3) . . . . ?
C12 C13 C8 C9 0.5(3) . . . . ?
C14 C13 C8 C9 179.6(2) . . . . ?
C12 C13 C8 C2 -179.41(19) . . . . ?
C14 C13 C8 C2 -0.2(3) . . . . ?
N1 C2 C8 C9 151.2(2) . . . . ?
N2 C2 C8 C9 -26.5(3) . . . . ?
N1 C2 C8 C13 -28.9(3) . . . . ?
N2 C2 C8 C13 153.4(2) . . . . ?
C2 N1 C1 C7 177.9(3) . . . . ?
C2 N1 C1 C3 -0.7(2) . . . . ?
C13 C8 C9 C10 -0.4(3) . . . . ?
C2 C8 C9 C10 179.5(2) . . . . ?
C11 C10 C9 C8 -0.6(3) . . . . ?
C12 C13 C14 C15 -1.2(3) . . . . ?
C8 C13 C14 C15 179.6(2) . . . . ?
C2 N2 C3 C4 -179.8(3) . . . . ?
C2 N2 C3 C1 0.3(2) . . . . ?
N1 C1 C3 N2 0.3(2) . . . . ?
C7 C1 C3 N2 -178.5(2) . . . . ?
N1 C1 C3 C4 -179.6(2) . . . . ?
C7 C1 C3 C4 1.6(4) . . . . ?
N1 C1 C7 C6 -180.0(3) . . . . ?
C3 C1 C7 C6 -1.5(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C12 N3 C16 C15 -0.4(4) . . . . ?
C14 C15 C16 N3 0.3(5) . . . . ?
C17 N4 C29 C30 29(3) . . . . ?
C21 N4 C29 C30 158(2) . . . . ?
C25 N4 C29 C30 -83(3) . . . . ?
N2 C3 C4 C5 179.7(3) . . . . ?
C1 C3 C4 C5 -0.4(4) . . . . ?
C1 C7 C6 C5 0.3(5) . . . . ?
C17 N4 C21 C22 -56.4(3) . . . . ?
C25 N4 C21 C22 56.4(8) . . . . ?
C37 N4 C21 C22 -174.6(5) . . . . ?
C29 N4 C21 C22 172.7(13) . . . . ?
C2A N4 C21 C22 68.9(10) . . . . ?
C21 N4 C17 C18 -58.6(3) . . . . ?
C25 N4 C17 C18 -176.6(12) . . . . ?
C37 N4 C17 C18 56.6(5) . . . . ?
C29 N4 C17 C18 69.6(11) . . . . ?
C2A N4 C17 C18 176.5(14) . . . . ?
N4 C21 C22 C23 -168.4(3) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C7 C6 C5 C4 0.9(5) . . . . ?
C21 C22 C23 C24 70.8(4) . . . . ?
N4 C17 C18 C19 179.2(3) . . . . ?
N4 C29 C30 C31 171(2) . . . . ?
C17 C18 C19 C20 -180.0(5) . . . . ?
C29 C30 C31 C34 -70(3) . . . . ?
C17 N4 C25 C36 179.2(14) . . . . ?
C21 N4 C25 C36 60.7(18) . . . . ?
C29 N4 C25 C36 -59(2) . . . . ?
N4 C25 C36 C35 171.3(15) . . . . ?
C25 C36 C35 C28 -158.4(17) . . . . ?
C5A C27 C26 C2A 92(3) . . . . ?
C27 C26 C2A N4 167(2) . . . . ?
C17 N4 C2A C26 178(2) . . . . ?
C21 N4 C2A C26 53(3) . . . . ?
C37 N4 C2A C26 -61(3) . . . . ?
C32 C0 C33 C37 175.1(12) . . . . ?
C17 N4 C37 C33 67.5(11) . . . . ?
C21 N4 C37 C33 -173.0(9) . . . . ?
C2A N4 C37 C33 -54.6(15) . . . . ?
C0 C33 C37 N4 171.5(9) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_24diohbicyc
_database_code_depnum_ccdc_archive 'CCDC 2394711'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-10-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 O2, H O0.5'
_chemical_formula_sum            'C13 H11 N2 O2.50'
_chemical_formula_weight         235.24
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8217(9)
_cell_length_b                   5.7898(11)
_cell_length_c                   24.196(5)
_cell_angle_alpha                94.416(7)
_cell_angle_beta                 91.100(9)
_cell_angle_gamma                93.667(8)
_cell_volume                     532.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1178
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.980
_cell_measurement_theta_min      0.978
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8067
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_min         2.534
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   microfocus
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1178
_reflns_number_total             2435
_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       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1660
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.084
_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)+(0.0624P)²+0.2484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.2003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-H3
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), C10(H10), C13(H13), C7(H7), C12(H12), C4(H4), C5(H5), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
O2 O 0.5062(7) 0.1901(4) 0.72813(9) 0.0500(7) Uani 1 1 d . . . . .
H2 H 0.581248 0.248202 0.758367 0.075 Uiso 1 1 calc R U . . .
O1 O 0.4924(8) 0.3413(5) 0.53807(10) 0.0638(8) Uani 1 1 d . . . . .
H1 H 0.328851 0.242117 0.536799 0.096 Uiso 1 1 calc R U . . .
N1 N 0.8063(7) 0.4911(4) 0.80116(11) 0.0387(7) Uani 1 1 d . . . . .
N2 N 1.0486(7) 0.8284(4) 0.77700(11) 0.0409(7) Uani 1 1 d . . . . .
H2A H 1.115993 0.936591 0.756403 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7702(8) 0.5541(5) 0.70232(13) 0.0339(7) Uani 1 1 d . . . . .
C9 C 0.5919(8) 0.3349(5) 0.68853(13) 0.0369(8) Uani 1 1 d . . . . .
C3 C 1.0978(8) 0.8318(5) 0.83367(13) 0.0383(8) Uani 1 1 d . . . . .
C2 C 0.8736(8) 0.6221(5) 0.75953(13) 0.0353(8) Uani 1 1 d . . . . .
C1 C 0.9469(8) 0.6186(5) 0.84856(13) 0.0380(8) Uani 1 1 d . . . . .
C10 C 0.4995(9) 0.2661(5) 0.63385(13) 0.0422(8) Uani 1 1 d . . . . .
H10 H 0.383779 0.121524 0.624794 0.051 Uiso 1 1 calc R U . . .
C11 C 0.5793(9) 0.4120(6) 0.59292(13) 0.0422(8) Uani 1 1 d . . . . .
C13 C 0.8461(9) 0.6949(5) 0.65949(13) 0.0425(9) Uani 1 1 d . . . . .
H13 H 0.965290 0.838863 0.667760 0.051 Uiso 1 1 calc R U . . .
C7 C 0.9504(9) 0.5691(6) 0.90374(14) 0.0466(9) Uani 1 1 d . . . . .
H7 H 0.851228 0.429264 0.914532 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7506(9) 0.6277(6) 0.60538(14) 0.0458(9) Uani 1 1 d . . . . .
H12 H 0.800344 0.725981 0.577512 0.055 Uiso 1 1 calc R U . . .
C4 C 1.2550(9) 0.9977(6) 0.87219(15) 0.0475(9) Uani 1 1 d . . . . .
H4 H 1.355247 1.137927 0.861768 0.057 Uiso 1 1 calc R U . . .
C5 C 1.2552(10) 0.9445(6) 0.92676(16) 0.0521(10) Uani 1 1 d . . . . .
H5 H 1.357225 1.051566 0.953930 0.063 Uiso 1 1 calc R U . . .
C6 C 1.1063(10) 0.7346(7) 0.94199(15) 0.0537(10) Uani 1 1 d . . . . .
H6 H 1.111849 0.704693 0.979201 0.064 Uiso 1 1 calc R U . . .
O3 O 1.000000 1.000000 0.500000 0.120(2) Uani 1 2 d DS . P . .
H3 H 0.850(15) 1.101(10) 0.499(3) 0.15(3) Uiso 1 1 d 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
O2 H2 0.8200 . ?
O2 C9 1.352(4) . ?
O1 H1 0.8200 . ?
O1 C11 1.386(4) . ?
N1 C2 1.326(4) . ?
N1 C1 1.395(4) . ?
N2 H2A 0.8600 . ?
N2 C3 1.379(4) . ?
N2 C2 1.364(4) . ?
C8 C9 1.414(4) . ?
C8 C2 1.450(4) . ?
C8 C13 1.391(4) . ?
C9 C10 1.384(4) . ?
C3 C1 1.404(4) . ?
C3 C4 1.385(5) . ?
C1 C7 1.387(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 C12 1.382(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.372(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.378(5) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?
O3 H3 0.843(19) 2_776 ?
O3 H3 0.843(19) . ?

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
C9 O2 H2 109.5 . . ?
C11 O1 H1 109.5 . . ?
C2 N1 C1 105.7(3) . . ?
C3 N2 H2A 126.2 . . ?
C2 N2 H2A 126.2 . . ?
C2 N2 C3 107.6(3) . . ?
C9 C8 C2 119.7(3) . . ?
C13 C8 C9 117.8(3) . . ?
C13 C8 C2 122.4(3) . . ?
O2 C9 C8 121.0(3) . . ?
O2 C9 C10 118.8(3) . . ?
C10 C9 C8 120.1(3) . . ?
N2 C3 C1 105.6(3) . . ?
N2 C3 C4 131.9(3) . . ?
C4 C3 C1 122.5(3) . . ?
N1 C2 N2 112.0(3) . . ?
N1 C2 C8 123.8(3) . . ?
N2 C2 C8 124.2(3) . . ?
N1 C1 C3 109.1(3) . . ?
C7 C1 N1 131.1(3) . . ?
C7 C1 C3 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 O1 119.9(3) . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 O1 119.0(3) . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 122.0(3) . . ?
C12 C13 H13 119.0 . . ?
C1 C7 H7 121.2 . . ?
C6 C7 C1 117.6(3) . . ?
C6 C7 H7 121.2 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C3 C4 H4 121.7 . . ?
C5 C4 C3 116.6(3) . . ?
C5 C4 H4 121.7 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 122.1(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
H3 O3 H3 180.00(14) . 2_776 ?

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 C9 C10 C11 179.0(3) . . . . ?
O1 C11 C12 C13 -178.0(3) . . . . ?
N1 C1 C7 C6 -178.7(3) . . . . ?
N2 C3 C1 N1 -0.6(3) . . . . ?
N2 C3 C1 C7 -179.4(3) . . . . ?
N2 C3 C4 C5 179.3(3) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C8 C13 C12 C11 -1.2(5) . . . . ?
C9 C8 C2 N1 -1.1(5) . . . . ?
C9 C8 C2 N2 179.5(3) . . . . ?
C9 C8 C13 C12 0.6(5) . . . . ?
C9 C10 C11 O1 178.8(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C3 N2 C2 N1 -0.1(4) . . . . ?
C3 N2 C2 C8 179.4(3) . . . . ?
C3 C1 C7 C6 -0.2(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C2 N1 C1 C3 0.5(3) . . . . ?
C2 N1 C1 C7 179.1(3) . . . . ?
C2 N2 C3 C1 0.4(3) . . . . ?
C2 N2 C3 C4 -179.3(3) . . . . ?
C2 C8 C9 O2 2.1(5) . . . . ?
C2 C8 C9 C10 -178.4(3) . . . . ?
C2 C8 C13 C12 179.2(3) . . . . ?
C1 N1 C2 N2 -0.3(4) . . . . ?
C1 N1 C2 C8 -179.8(3) . . . . ?
C1 C3 C4 C5 -0.4(5) . . . . ?
C1 C7 C6 C5 0.1(5) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
C13 C8 C9 O2 -179.3(3) . . . . ?
C13 C8 C9 C10 0.2(5) . . . . ?
C13 C8 C2 N1 -179.7(3) . . . . ?
C13 C8 C2 N2 0.9(5) . . . . ?
C4 C3 C1 N1 179.1(3) . . . . ?
C4 C3 C1 C7 0.4(5) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?

_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_pra
_database_code_depnum_ccdc_archive 'CCDC 2387454'
loop_
_audit_author_name
_audit_author_address
'Priyanka Angarkhe'
;Institute of Chemical Technology Indian Oil Odisha Campus Bhubaneswar
India
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H46 F N3 O S'
_chemical_formula_sum            'C32 H46 F N3 O S'
_chemical_formula_weight         539.78

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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   8.2612(12)
_cell_length_b                   9.5452(14)
_cell_length_c                   9.9777(12)
_cell_angle_alpha                94.986(4)
_cell_angle_beta                 93.564(4)
_cell_angle_gamma                98.378(5)
_cell_volume                     773.21(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    3589
_cell_measurement_theta_min      0.974
_cell_measurement_theta_max      0.977

_exptl_crystal_description       Yellow
_exptl_crystal_colour            Block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18283
_diffrn_reflns_av_unetI/netI     0.0882
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         27.591
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             6329
_reflns_number_gt                4506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_max     0.781
_reflns_Friedel_fraction_full    0.830

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          '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)+(0.0475P)²+0.0634P] 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 1469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6329
_refine_ls_number_parameters     377
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.76220(12) 0.02399(10) 1.20177(10) 0.0608(3) Uani 1 1 d . . . . .
O1 O 0.6492(4) 0.4999(4) 1.6900(3) 0.0770(9) Uani 1 1 d D . . . .
H1 H 0.727(17) 0.512(19) 1.754(14) 0.39(10) Uiso 1 1 d D . . . .
N3 N 0.7992(4) 0.6562(4) 1.5028(3) 0.0646(9) Uani 1 1 d . . . . .
N1 N 0.7636(4) 0.2500(3) 1.0754(3) 0.0486(7) Uani 1 1 d . . . . .
C13 C 0.7834(4) 0.4413(3) 1.3476(3) 0.0426(7) Uani 1 1 d . . . . .
C12 C 0.7539(4) 0.5141(4) 1.4731(3) 0.0473(8) Uani 1 1 d . . . . .
C3 C 0.7710(4) 0.0043(4) 1.0281(4) 0.0518(8) Uani 1 1 d . . . . .
C4 C 0.7752(4) -0.1179(4) 0.9432(4) 0.0589(9) Uani 1 1 d . . . . .
H4 H 0.774768 -0.205540 0.977413 0.071 Uiso 1 1 calc R U . . .
C8 C 0.7325(4) 0.2910(3) 1.3217(3) 0.0450(8) Uani 1 1 d . . . . .
C14 C 0.8669(4) 0.5262(4) 1.2565(3) 0.0526(8) Uani 1 1 d . . . . .
H14 H 0.894134 0.483941 1.175099 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7812(5) 0.0247(5) 0.7569(4) 0.0703(11) Uani 1 1 d . . . . .
H6 H 0.783391 0.030524 0.664495 0.084 Uiso 1 1 calc R U . . .
C2 C 0.7543(4) 0.2074(3) 1.1960(3) 0.0452(7) Uani 1 1 d . . . . .
C9 C 0.6554(4) 0.2222(4) 1.4226(4) 0.0546(9) Uani 1 1 d . . . . .
H9 H 0.621474 0.124545 1.407665 0.066 Uiso 1 1 calc R U . . .
C1 C 0.7729(4) 0.1369(4) 0.9793(3) 0.0502(8) Uani 1 1 d . . . . .
C10 C 0.6265(5) 0.2911(4) 1.5439(4) 0.0588(9) Uani 1 1 d . . . . .
H10 H 0.572465 0.238220 1.606294 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6746(4) 0.4364(4) 1.5771(3) 0.0565(9) Uani 1 1 d . . . . .
C7 C 0.7790(5) 0.1473(4) 0.8415(4) 0.0643(10) Uani 1 1 d . . . . .
H7 H 0.781649 0.234913 0.806829 0.077 Uiso 1 1 calc R U . . .
C16 C 0.8693(5) 0.7290(4) 1.4111(5) 0.0683(11) Uani 1 1 d . . . . .
H16 H 0.895231 0.827157 1.430343 0.082 Uiso 1 1 calc R U . . .
C5 C 0.7801(5) -0.1062(4) 0.8065(4) 0.0648(11) Uani 1 1 d . . . . .
H5 H 0.782623 -0.186727 0.747563 0.078 Uiso 1 1 calc R U . . .
C15 C 0.9078(5) 0.6697(4) 1.2870(4) 0.0654(10) Uani 1 1 d . . . . .
H15 H 0.960096 0.726313 1.226444 0.078 Uiso 1 1 calc R U . . .
F1 F 0.8228(4) 0.5293(3) 0.9281(3) 0.0992(9) Uani 1 1 d . . . . .
N4 N 1.2682(4) 0.6495(3) 0.7870(3) 0.0543(8) Uani 1 1 d D . . . .
C29 C 1.149(3) 0.742(3) 0.851(4) 0.069(3) Uani 0.365(14) 1 d D . P A 2
H29A H 1.078164 0.768034 0.779503 0.083 Uiso 0.365(14) 1 calc R U P A 2
H29B H 1.080034 0.683774 0.907016 0.083 Uiso 0.365(14) 1 calc R U P A 2
C19 C 1.4135(6) 0.5055(6) 1.1213(5) 0.0850(14) Uani 1 1 d . . . . .
H19A H 1.478075 0.437563 1.082089 0.102 Uiso 1 1 calc R U . . .
H19B H 1.487718 0.591936 1.153411 0.102 Uiso 1 1 calc R U . . .
C35 C 1.1838(17) 0.7707(13) 0.847(2) 0.069(3) Uani 0.635(14) 1 d D . P A 1
H35A H 1.123694 0.806393 0.773852 0.083 Uiso 0.635(14) 1 calc R U P A 1
H35B H 1.104319 0.731768 0.906604 0.083 Uiso 0.635(14) 1 calc R U P A 1
C36 C 1.2944(16) 0.8936(12) 0.9236(18) 0.112(4) Uani 0.635(14) 1 d D . P A 1
H36A H 1.354855 0.858290 0.996695 0.134 Uiso 0.635(14) 1 calc R U P A 1
H36B H 1.373484 0.933353 0.863977 0.134 Uiso 0.635(14) 1 calc R U P A 1
C25 C 1.3809(5) 0.7116(4) 0.6854(4) 0.0585(9) Uani 1 1 d . . . . .
H25A H 1.453019 0.793596 0.730555 0.070 Uiso 1 1 calc R U . . .
H25B H 1.449093 0.641420 0.657365 0.070 Uiso 1 1 calc R U . . .
C23 C 1.0885(6) 0.2963(5) 0.5796(7) 0.0996(18) Uani 1 1 d . . . . .
H23A H 1.029793 0.341623 0.512552 0.120 Uiso 1 1 calc R U . . .
H23B H 1.010658 0.263252 0.643177 0.120 Uiso 1 1 calc R U . . .
C34 C 1.304(2) 1.1308(13) 1.019(2) 0.180(9) Uani 0.635(14) 1 d D . P A 1
H34A H 1.361345 1.163131 0.943346 0.270 Uiso 0.635(14) 1 calc R U P A 1
H34B H 1.382525 1.118518 1.090211 0.270 Uiso 0.635(14) 1 calc R U P A 1
H34C H 1.237991 1.199843 1.049535 0.270 Uiso 0.635(14) 1 calc R U P A 1
C31 C 1.282(3) 0.999(2) 0.863(3) 0.138(8) Uani 0.365(14) 1 d D . P A 2
H31A H 1.400297 1.005576 0.858811 0.166 Uiso 0.365(14) 1 calc R U P A 2
H31B H 1.234162 0.979307 0.770764 0.166 Uiso 0.365(14) 1 calc R U P A 2
C20 C 1.3301(8) 0.4452(7) 1.2395(6) 0.1060(18) Uani 1 1 d . . . . .
H20A H 1.263615 0.355590 1.209396 0.159 Uiso 1 1 calc R U . . .
H20B H 1.262047 0.510298 1.275909 0.159 Uiso 1 1 calc R U . . .
H20C H 1.411737 0.431652 1.307876 0.159 Uiso 1 1 calc R U . . .
C22 C 1.2171(5) 0.4052(5) 0.6531(5) 0.0712(12) Uani 1 1 d . . . . .
H22A H 1.294134 0.441632 0.590330 0.085 Uiso 1 1 calc R U . . .
H22B H 1.276827 0.361685 0.720829 0.085 Uiso 1 1 calc R U . . .
C27 C 1.4215(6) 0.8249(6) 0.4721(5) 0.0883(14) Uani 1 1 d . . . . .
H27A H 1.498409 0.759922 0.451354 0.106 Uiso 1 1 calc R U . . .
H27B H 1.482761 0.910036 0.521750 0.106 Uiso 1 1 calc R U . . .
C18 C 1.2900(5) 0.5387(5) 1.0129(4) 0.0696(11) Uani 1 1 d . . . . .
H18A H 1.216653 0.452231 0.979342 0.084 Uiso 1 1 calc R U . . .
H18B H 1.224589 0.606124 1.051770 0.084 Uiso 1 1 calc R U . . .
C24 C 1.1461(8) 0.1706(6) 0.5110(7) 0.111(2) Uani 1 1 d . . . . .
H24A H 1.230339 0.201645 0.453349 0.167 Uiso 1 1 calc R U . . .
H24B H 1.055916 0.112686 0.457877 0.167 Uiso 1 1 calc R U . . .
H24C H 1.189496 0.116034 0.577271 0.167 Uiso 1 1 calc R U . . .
C21 C 1.1441(5) 0.5273(4) 0.7206(4) 0.0598(9) Uani 1 1 d . . . . .
H21A H 1.075073 0.563372 0.653616 0.072 Uiso 1 1 calc R U . . .
H21B H 1.074327 0.490905 0.788411 0.072 Uiso 1 1 calc R U . . .
C28 C 1.3461(7) 0.8643(6) 0.3420(5) 0.0901(15) Uani 1 1 d . . . . .
H28A H 1.284913 0.780732 0.292174 0.135 Uiso 1 1 calc R U . . .
H28B H 1.431310 0.904767 0.289440 0.135 Uiso 1 1 calc R U . . .
H28C H 1.274069 0.932557 0.361467 0.135 Uiso 1 1 calc R U . . .
C17 C 1.3771(5) 0.6002(4) 0.8974(4) 0.0602(9) Uani 1 1 d . . . . .
H17A H 1.435912 0.528925 0.856119 0.072 Uiso 1 1 calc R U . . .
H17B H 1.457990 0.680569 0.934162 0.072 Uiso 1 1 calc R U . . .
C33 C 1.2100(14) 1.0086(11) 0.9808(17) 0.137(6) Uani 0.635(14) 1 d D . P A 1
H33A H 1.125825 1.024634 0.914130 0.164 Uiso 0.635(14) 1 calc R U P A 1
H33B H 1.155341 0.976485 1.058367 0.164 Uiso 0.635(14) 1 calc R U P A 1
C30 C 1.227(3) 0.8741(19) 0.935(3) 0.112(4) Uani 0.365(14) 1 d D . P A 2
H30A H 1.148964 0.900775 0.998060 0.134 Uiso 0.365(14) 1 calc R U P A 2
H30B H 1.320766 0.852124 0.988286 0.134 Uiso 0.365(14) 1 calc R U P A 2
C32 C 1.253(6) 1.121(3) 0.907(4) 0.21(2) Uani 0.365(14) 1 d D . P A 2
H32A H 1.167334 1.110898 0.967072 0.322 Uiso 0.365(14) 1 calc R U P A 2
H32B H 1.220022 1.170583 0.832242 0.322 Uiso 0.365(14) 1 calc R U P A 2
H32C H 1.350863 1.174786 0.953830 0.322 Uiso 0.365(14) 1 calc R U P A 2
C26 C 1.2982(5) 0.7567(5) 0.5605(5) 0.0670(10) Uani 1 1 d . . . . .
H26A H 1.232548 0.674231 0.509971 0.080 Uiso 1 1 calc R U . . .
H26B H 1.225312 0.823554 0.586732 0.080 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
S1 C3 1.734(4) . ?
S1 C2 1.767(3) . ?
O1 C11 1.276(4) . ?
O1 H1 0.86(3) . ?
N3 C16 1.309(6) . ?
N3 C12 1.355(5) . ?
N1 C2 1.307(4) . ?
N1 C1 1.393(4) . ?
C13 C14 1.415(5) . ?
C13 C12 1.431(4) . ?
C13 C8 1.431(5) . ?
C12 C11 1.461(5) . ?
C3 C4 1.387(5) . ?
C3 C1 1.393(5) . ?
C4 C5 1.380(6) . ?
C4 H4 0.9300 . ?
C8 C9 1.387(5) . ?
C8 C2 1.462(4) . ?
C14 C15 1.364(5) . ?
C14 H14 0.9300 . ?
C6 C5 1.382(6) . ?
C6 C7 1.386(5) . ?
C6 H6 0.9300 . ?
C9 C10 1.377(5) . ?
C9 H9 0.9300 . ?
C1 C7 1.391(5) . ?
C10 C11 1.390(6) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C16 C15 1.391(6) . ?
C16 H16 0.9300 . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
N4 C21 1.511(5) . ?
N4 C25 1.519(5) . ?
N4 C17 1.527(5) . ?
N4 C35 1.532(10) . ?
N4 C29 1.545(18) . ?
C29 C30 1.492(18) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C19 C20 1.517(7) . ?
C19 C18 1.525(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C35 C36 1.497(12) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 C33 1.477(13) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C25 C26 1.509(6) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C23 C22 1.482(6) . ?
C23 C24 1.484(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C34 C33 1.316(14) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C31 C32 1.27(2) . ?
C31 C30 1.48(2) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 C21 1.514(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C27 C26 1.502(6) . ?
C27 C28 1.505(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C18 C17 1.513(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?

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
C3 S1 C2 89.96(16) . . ?
C11 O1 H1 118(10) . . ?
C16 N3 C12 118.2(3) . . ?
C2 N1 C1 111.2(3) . . ?
C14 C13 C12 115.9(3) . . ?
C14 C13 C8 124.0(3) . . ?
C12 C13 C8 120.1(3) . . ?
N3 C12 C13 122.5(3) . . ?
N3 C12 C11 116.7(3) . . ?
C13 C12 C11 120.7(3) . . ?
C4 C3 C1 121.9(4) . . ?
C4 C3 S1 129.2(3) . . ?
C1 C3 S1 108.8(3) . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C9 C8 C13 117.1(3) . . ?
C9 C8 C2 118.7(3) . . ?
C13 C8 C2 124.2(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C5 C6 C7 121.6(4) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
N1 C2 C8 128.1(3) . . ?
N1 C2 S1 114.0(2) . . ?
C8 C2 S1 117.8(2) . . ?
C10 C9 C8 123.4(3) . . ?
C10 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C7 C1 C3 119.2(3) . . ?
C7 C1 N1 124.9(3) . . ?
C3 C1 N1 115.9(3) . . ?
C9 C10 C11 122.8(3) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
O1 C11 C10 122.8(4) . . ?
O1 C11 C12 121.3(4) . . ?
C10 C11 C12 115.9(3) . . ?
C6 C7 C1 118.7(4) . . ?
C6 C7 H7 120.7 . . ?
C1 C7 H7 120.7 . . ?
N3 C16 C15 124.5(4) . . ?
N3 C16 H16 117.8 . . ?
C15 C16 H16 117.8 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C14 C15 C16 118.3(4) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C21 N4 C25 111.0(3) . . ?
C21 N4 C17 111.0(3) . . ?
C25 N4 C17 107.0(3) . . ?
C21 N4 C35 111.2(6) . . ?
C25 N4 C35 106.8(8) . . ?
C17 N4 C35 109.6(10) . . ?
C21 N4 C29 98.9(10) . . ?
C25 N4 C29 118.9(15) . . ?
C17 N4 C29 109.9(18) . . ?
C30 C29 N4 115.9(19) . . ?
C30 C29 H29A 108.3 . . ?
N4 C29 H29A 108.3 . . ?
C30 C29 H29B 108.3 . . ?
N4 C29 H29B 108.3 . . ?
H29A C29 H29B 107.4 . . ?
C20 C19 C18 112.0(4) . . ?
C20 C19 H19A 109.2 . . ?
C18 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
C18 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C36 C35 N4 116.0(10) . . ?
C36 C35 H35A 108.3 . . ?
N4 C35 H35A 108.3 . . ?
C36 C35 H35B 108.3 . . ?
N4 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
C33 C36 C35 114.9(10) . . ?
C33 C36 H36A 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C33 C36 H36B 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C26 C25 N4 116.3(3) . . ?
C26 C25 H25A 108.2 . . ?
N4 C25 H25A 108.2 . . ?
C26 C25 H25B 108.2 . . ?
N4 C25 H25B 108.2 . . ?
H25A C25 H25B 107.4 . . ?
C22 C23 C24 116.1(4) . . ?
C22 C23 H23A 108.3 . . ?
C24 C23 H23A 108.3 . . ?
C22 C23 H23B 108.3 . . ?
C24 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C31 C30 120(2) . . ?
C32 C31 H31A 107.4 . . ?
C30 C31 H31A 107.4 . . ?
C32 C31 H31B 107.4 . . ?
C30 C31 H31B 107.4 . . ?
H31A C31 H31B 106.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C22 C21 111.5(4) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C26 C27 C28 113.7(4) . . ?
C26 C27 H27A 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C17 C18 C19 110.6(4) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N4 C21 C22 114.9(3) . . ?
N4 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N4 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C18 C17 N4 116.0(3) . . ?
C18 C17 H17A 108.3 . . ?
N4 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
N4 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C34 C33 C36 115.6(11) . . ?
C34 C33 H33A 108.4 . . ?
C36 C33 H33A 108.4 . . ?
C34 C33 H33B 108.4 . . ?
C36 C33 H33B 108.4 . . ?
H33A C33 H33B 107.4 . . ?
C31 C30 C29 117(2) . . ?
C31 C30 H30A 108.1 . . ?
C29 C30 H30A 108.1 . . ?
C31 C30 H30B 108.1 . . ?
C29 C30 H30B 108.1 . . ?
H30A C30 H30B 107.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C26 C25 111.5(4) . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
C25 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?

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
C16 N3 C12 C13 1.5(5) . . . . ?
C16 N3 C12 C11 -179.5(3) . . . . ?
C14 C13 C12 N3 1.5(5) . . . . ?
C8 C13 C12 N3 -179.9(3) . . . . ?
C14 C13 C12 C11 -177.5(3) . . . . ?
C8 C13 C12 C11 1.1(5) . . . . ?
C2 S1 C3 C4 -177.8(3) . . . . ?
C2 S1 C3 C1 1.9(3) . . . . ?
C1 C3 C4 C5 -0.5(5) . . . . ?
S1 C3 C4 C5 179.2(3) . . . . ?
C14 C13 C8 C9 178.4(3) . . . . ?
C12 C13 C8 C9 -0.1(5) . . . . ?
C14 C13 C8 C2 -2.6(5) . . . . ?
C12 C13 C8 C2 178.9(3) . . . . ?
C12 C13 C14 C15 -3.1(5) . . . . ?
C8 C13 C14 C15 178.4(4) . . . . ?
C1 N1 C2 C8 -175.8(3) . . . . ?
C1 N1 C2 S1 1.7(4) . . . . ?
C9 C8 C2 N1 151.8(3) . . . . ?
C13 C8 C2 N1 -27.1(5) . . . . ?
C9 C8 C2 S1 -25.6(4) . . . . ?
C13 C8 C2 S1 155.5(3) . . . . ?
C3 S1 C2 N1 -2.2(3) . . . . ?
C3 S1 C2 C8 175.6(3) . . . . ?
C13 C8 C9 C10 0.0(5) . . . . ?
C2 C8 C9 C10 -179.0(3) . . . . ?
C4 C3 C1 C7 0.0(5) . . . . ?
S1 C3 C1 C7 -179.7(3) . . . . ?
C4 C3 C1 N1 178.3(3) . . . . ?
S1 C3 C1 N1 -1.5(4) . . . . ?
C2 N1 C1 C7 178.0(4) . . . . ?
C2 N1 C1 C3 -0.2(4) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C9 C10 C11 O1 -179.3(4) . . . . ?
C9 C10 C11 C12 2.0(5) . . . . ?
N3 C12 C11 O1 0.2(5) . . . . ?
C13 C12 C11 O1 179.3(3) . . . . ?
N3 C12 C11 C10 178.9(3) . . . . ?
C13 C12 C11 C10 -2.0(5) . . . . ?
C5 C6 C7 C1 -1.1(6) . . . . ?
C3 C1 C7 C6 0.8(6) . . . . ?
N1 C1 C7 C6 -177.3(4) . . . . ?
C12 N3 C16 C15 -3.1(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C7 C6 C5 C4 0.6(6) . . . . ?
C13 C14 C15 C16 1.7(6) . . . . ?
N3 C16 C15 C14 1.5(6) . . . . ?
C21 N4 C29 C30 177(2) . . . . ?
C25 N4 C29 C30 -63(3) . . . . ?
C17 N4 C29 C30 61(3) . . . . ?
C21 N4 C35 C36 176.0(12) . . . . ?
C25 N4 C35 C36 -62.8(16) . . . . ?
C17 N4 C35 C36 52.8(16) . . . . ?
N4 C35 C36 C33 -179.7(17) . . . . ?
C21 N4 C25 C26 54.0(4) . . . . ?
C17 N4 C25 C26 175.2(3) . . . . ?
C35 N4 C25 C26 -67.5(9) . . . . ?
C29 N4 C25 C26 -59.7(17) . . . . ?
C24 C23 C22 C21 -179.2(5) . . . . ?
C20 C19 C18 C17 179.3(4) . . . . ?
C25 N4 C21 C22 58.6(5) . . . . ?
C17 N4 C21 C22 -60.3(4) . . . . ?
C35 N4 C21 C22 177.4(10) . . . . ?
C29 N4 C21 C22 -175.7(18) . . . . ?
C23 C22 C21 N4 -174.6(4) . . . . ?
C19 C18 C17 N4 -175.2(3) . . . . ?
C21 N4 C17 C18 -60.8(4) . . . . ?
C25 N4 C17 C18 178.0(3) . . . . ?
C35 N4 C17 C18 62.5(7) . . . . ?
C29 N4 C17 C18 47.6(11) . . . . ?
C35 C36 C33 C34 -163.7(17) . . . . ?
C32 C31 C30 C29 136(3) . . . . ?
N4 C29 C30 C31 81(4) . . . . ?
C28 C27 C26 C25 176.6(4) . . . . ?
N4 C25 C26 C27 176.3(4) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.033



