# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_2C
_database_code_depnum_ccdc_archive 'CCDC 1961234'
loop_
_audit_author_name
_audit_author_address
'Dr. E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N O3'
_chemical_formula_weight         219.23

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'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8505(12)
_cell_length_b                   11.594(2)
_cell_length_c                   16.205(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1099.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1264
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.35

_exptl_crystal_description       PLATES
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9691
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5494
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1934
_reflns_number_gt                1688
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0303P)²+1.2669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(3)
_refine_ls_number_reflns         1934
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.0539(6) 1.2103(2) 0.12160(17) 0.0242(8) Uani 1 1 d . . .
H2C H 0.0268 1.2435 0.0780 0.036 Uiso 1 1 calc R . .
O1 O -0.2125(5) 1.0122(2) 0.05035(18) 0.0258(8) Uani 1 1 d . . .
O3 O 0.4607(5) 1.1703(2) 0.0215(2) 0.0276(8) Uani 1 1 d . . .
H3C H 0.5782 1.1332 0.0290 0.041 Uiso 1 1 calc R . .
C7 C -0.0530(7) 1.0093(3) 0.0999(2) 0.0179(10) Uani 1 1 d . . .
C1 C 0.2772(8) 1.0543(3) 0.1771(2) 0.0165(9) Uani 1 1 d . . .
N1 N -0.0146(6) 0.9263(3) 0.1559(2) 0.0182(8) Uani 1 1 d . . .
C8 C 0.1399(7) 1.0987(4) 0.1048(2) 0.0164(10) Uani 1 1 d . . .
C6 C 0.1818(7) 0.9525(3) 0.2042(3) 0.0152(9) Uani 1 1 d . . .
C10 C -0.0684(9) 0.7212(4) 0.1212(3) 0.0290(12) Uani 1 1 d . . .
C12 C 0.2703(7) 1.0947(4) 0.0226(3) 0.0221(10) Uani 1 1 d . . .
H12A H 0.3227 1.0165 0.0128 0.027 Uiso 1 1 calc R . .
H12B H 0.1671 1.1154 -0.0218 0.027 Uiso 1 1 calc R . .
C2 C 0.4698(8) 1.0970(4) 0.2160(3) 0.0240(11) Uani 1 1 d . . .
H2A H 0.5361 1.1657 0.1985 0.029 Uiso 1 1 calc R . .
C9 C -0.1571(8) 0.8243(4) 0.1662(3) 0.0243(11) Uani 1 1 d . . .
C3 C 0.5625(8) 1.0360(4) 0.2813(3) 0.0256(11) Uani 1 1 d . . .
C5 C 0.2712(8) 0.8900(4) 0.2692(3) 0.0259(11) Uani 1 1 d . . .
C11 C 0.1076(10) 0.7172(5) 0.0727(3) 0.0333(13) Uani 1 1 d . . .
C4 C 0.4638(9) 0.9347(4) 0.3067(2) 0.0260(11) Uani 1 1 d . . .
H4 H 0.5287 0.8947 0.3506 0.031 Uiso 1 1 calc R . .
H5 H 0.193(8) 0.824(4) 0.290(3) 0.030(13) Uiso 1 1 d . . .
H9B H -0.165(7) 0.805(4) 0.223(3) 0.021(12) Uiso 1 1 d . . .
H10 H -0.155(7) 0.657(4) 0.130(2) 0.013(11) Uiso 1 1 d . . .
H9A H -0.299(8) 0.850(4) 0.144(3) 0.028(13) Uiso 1 1 d . . .
H11B H 0.151(8) 0.650(4) 0.042(3) 0.033(13) Uiso 1 1 d . . .
H3 H 0.702(7) 1.069(3) 0.309(2) 0.014(11) Uiso 1 1 d . . .
H11A H 0.194(7) 0.780(4) 0.066(2) 0.017(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.415(5) . ?
O2 H2C 0.8200 . ?
O1 C7 1.231(5) . ?
O3 C12 1.417(5) . ?
O3 H3C 0.8200 . ?
C7 N1 1.341(5) . ?
C7 C8 1.535(6) . ?
C1 C6 1.377(5) . ?
C1 C2 1.383(6) . ?
C1 C8 1.511(6) . ?
N1 C6 1.423(5) . ?
N1 C9 1.456(5) . ?
C8 C12 1.536(6) . ?
C6 C5 1.382(6) . ?
C10 C11 1.296(7) . ?
C10 C9 1.494(6) . ?
C10 H10 0.91(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 C3 1.384(6) . ?
C2 H2A 0.9300 . ?
C9 H9B 0.95(4) . ?
C9 H9A 0.96(5) . ?
C3 C4 1.372(6) . ?
C3 H3 1.01(4) . ?
C5 C4 1.380(6) . ?
C5 H5 0.95(5) . ?
C11 H11B 0.96(5) . ?
C11 H11A 0.89(4) . ?
C4 H4 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
C8 O2 H2C 109.5 . . ?
C12 O3 H3C 109.5 . . ?
O1 C7 N1 126.0(4) . . ?
O1 C7 C8 124.9(4) . . ?
N1 C7 C8 109.0(3) . . ?
C6 C1 C2 119.5(4) . . ?
C6 C1 C8 108.9(4) . . ?
C2 C1 C8 131.6(4) . . ?
C7 N1 C6 110.8(3) . . ?
C7 N1 C9 124.3(4) . . ?
C6 N1 C9 124.9(4) . . ?
O2 C8 C1 110.6(3) . . ?
O2 C8 C7 111.5(3) . . ?
C1 C8 C7 101.6(3) . . ?
O2 C8 C12 111.8(3) . . ?
C1 C8 C12 113.5(3) . . ?
C7 C8 C12 107.5(3) . . ?
C1 C6 C5 122.6(4) . . ?
C1 C6 N1 109.6(4) . . ?
C5 C6 N1 127.9(4) . . ?
C11 C10 C9 126.9(5) . . ?
C11 C10 H10 121(2) . . ?
C9 C10 H10 113(2) . . ?
O3 C12 C8 112.5(3) . . ?
O3 C12 H12A 109.1 . . ?
C8 C12 H12A 109.1 . . ?
O3 C12 H12B 109.1 . . ?
C8 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
N1 C9 C10 113.3(4) . . ?
N1 C9 H9B 109(3) . . ?
C10 C9 H9B 108(3) . . ?
N1 C9 H9A 101(3) . . ?
C10 C9 H9A 111(3) . . ?
H9B C9 H9A 114(4) . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 122(2) . . ?
C2 C3 H3 118(2) . . ?
C4 C5 C6 116.6(4) . . ?
C4 C5 H5 123(3) . . ?
C6 C5 H5 120(3) . . ?
C10 C11 H11B 124(3) . . ?
C10 C11 H11A 120(3) . . ?
H11B C11 H11A 116(4) . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_2G
_database_code_depnum_ccdc_archive 'CCDC 1961238'
loop_
_audit_author_name
_audit_author_address
'Dr. E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         303.73
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+3/4, -y+5/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+5/4, -y+3/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+5/4, -y+5/4, z+1/4'

_cell_length_a                   62.210(8)
_cell_length_b                   17.713(2)
_cell_length_c                   5.2259(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5758.6(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3579
_cell_measurement_theta_min      2.3900
_cell_measurement_theta_max      21.4440
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       ROD
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.068
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2528

_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'


_exptl_absorpt_correction_T_min  0.9060
_exptl_absorpt_correction_T_max  0.9820

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            18150
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_unetI/netI     0.1146
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -82
_diffrn_reflns_limit_h_max       81
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             18150
_reflns_number_gt                9343
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1730
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_number_reflns         18150
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_abs_structure_details 
;

Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)

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'
Cl Cl 0.1484 0.1585 '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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.04675(4) 0.03529(11) 0.8539(6) 0.0880(10) Uani d . . . 1 . .
O O1 0.09404(7) 0.4163(3) 0.7820(10) 0.0495(14) Uani d . . . 1 . .
O O2 0.10509(8) 0.3404(3) 1.2511(9) 0.0515(16) Uani d . . . 1 . .
H H2A 0.1111(13) 0.316(3) 1.352(13) 0.077 Uiso calc U . R 1 . .
O O3 0.12450(8) 0.2623(3) 0.6517(9) 0.0518(14) Uani d . . . 1 . .
H H3A 0.134345 0.232249 0.616633 0.078 Uiso d U . R 1 . .
N N1 0.07464(9) 0.3079(3) 0.7336(11) 0.0386(15) Uani d . . . 1 . .
C C1 0.03351(14) 0.3910(5) 0.8419(19) 0.064(2) Uani d . . . 1 . .
H H1 0.045025 0.410426 0.934367 0.077 Uiso calc U . R 1 . .
C C2 0.01288(17) 0.4060(5) 0.920(2) 0.085(3) Uani d . . . 1 . .
H H2 0.010595 0.435122 1.065547 0.102 Uiso calc U . R 1 . .
C C3 -0.00409(17) 0.3791(7) 0.788(3) 0.096(4) Uani d . . . 1 . .
H H3 -0.018016 0.390483 0.840419 0.115 Uiso calc U . R 1 . .
C C4 -0.00072(14) 0.3356(6) 0.581(2) 0.090(3) Uani d . . . 1 . .
H H4 -0.012414 0.316472 0.490495 0.108 Uiso calc U . R 1 . .
C C5 0.02008(13) 0.3188(4) 0.4989(17) 0.067(3) Uani d . . . 1 . .
H H5 0.022262 0.288103 0.3568 0.08 Uiso calc U . R 1 . .
C C6 0.03733(11) 0.3479(4) 0.6301(15) 0.0452(19) Uani d . . . 1 . .
C C7 0.05991(10) 0.3346(4) 0.5343(15) 0.0444(18) Uani d . . . 1 . .
H H7A 0.059475 0.297625 0.397385 0.053 Uiso calc U . R 1 . .
H H7B 0.065446 0.381318 0.463477 0.053 Uiso calc U . R 1 . .
C C8 0.07423(11) 0.2354(4) 0.8410(14) 0.0398(18) Uani d . . . 1 . .
C C9 0.06042(11) 0.1771(4) 0.7849(16) 0.048(2) Uani d . . . 1 . .
H H9 0.049648 0.181953 0.662605 0.058 Uiso calc U . R 1 . .
C C10 0.06342(12) 0.1103(4) 0.9207(17) 0.055(2) Uani d . . . 1 . .
C C11 0.07926(13) 0.1029(4) 1.1028(17) 0.058(2) Uani d . . . 1 . .
H H11 0.080692 0.057914 1.19309 0.07 Uiso calc U . R 1 . .
C C12 0.09314(12) 0.1629(4) 1.1515(15) 0.051(2) Uani d . . . 1 . .
H H12 0.103994 0.157855 1.272651 0.061 Uiso calc U . R 1 . .
C C13 0.09074(11) 0.2292(4) 1.0202(14) 0.0392(18) Uani d . . . 1 . .
C C14 0.10375(11) 0.3003(4) 1.0149(14) 0.0376(17) Uani d . . . 1 . .
C C15 0.09081(11) 0.3502(4) 0.8327(14) 0.0390(18) Uani d . . . 1 . .
C C16 0.12621(11) 0.2890(4) 0.9094(13) 0.0437(19) Uani d . . . 1 . .
H H16A 0.13405 0.336369 0.913136 0.052 Uiso calc U . R 1 . .
H H16B 0.133941 0.252584 1.012959 0.052 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C10 . 1.721(7) ?
O1 C15 . 1.217(7) ?
O2 C14 . 1.427(8) ?
O2 H2A . 0.78(9) ?
O3 C16 . 1.431(8) ?
O3 H3A . 0.8325 ?
N1 C15 . 1.357(8) ?
N1 C8 . 1.401(8) ?
N1 C7 . 1.466(8) ?
C1 C6 . 1.366(11) ?
C1 C2 . 1.373(11) ?
C1 H1 . 0.93 ?
C2 C3 . 1.347(14) ?
C2 H2 . 0.93 ?
C3 C4 . 1.349(15) ?
C3 H3 . 0.93 ?
C4 C5 . 1.395(11) ?
C4 H4 . 0.93 ?
C5 C6 . 1.374(10) ?
C5 H5 . 0.93 ?
C6 C7 . 1.510(9) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.376(9) ?
C8 C13 . 1.395(9) ?
C9 C10 . 1.391(9) ?
C9 H9 . 0.93 ?
C10 C11 . 1.376(10) ?
C11 C12 . 1.392(10) ?
C11 H11 . 0.93 ?
C12 C13 . 1.370(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.497(9) ?
C14 C16 . 1.516(9) ?
C14 C15 . 1.529(9) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O2 H2A . . 109.5 ?
C16 O3 H3A . . 111.3 ?
C15 N1 C8 . . 111.5(6) ?
C15 N1 C7 . . 123.8(6) ?
C8 N1 C7 . . 124.6(6) ?
C6 C1 C2 . . 120.8(9) ?
C6 C1 H1 . . 119.6 ?
C2 C1 H1 . . 119.6 ?
C3 C2 C1 . . 120.8(11) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.4(11) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.8(10) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 119.5(9) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C1 C6 C5 . . 118.6(8) ?
C1 C6 C7 . . 121.2(7) ?
C5 C6 C7 . . 120.2(8) ?
N1 C7 C6 . . 113.3(6) ?
N1 C7 H7A . . 108.9 ?
C6 C7 H7A . . 108.9 ?
N1 C7 H7B . . 108.9 ?
C6 C7 H7B . . 108.9 ?
H7A C7 H7B . . 107.7 ?
C9 C8 C13 . . 123.0(7) ?
C9 C8 N1 . . 127.9(7) ?
C13 C8 N1 . . 109.1(6) ?
C8 C9 C10 . . 116.5(7) ?
C8 C9 H9 . . 121.8 ?
C10 C9 H9 . . 121.8 ?
C11 C10 C9 . . 122.0(7) ?
C11 C10 Cl1 . . 119.8(6) ?
C9 C10 Cl1 . . 118.2(7) ?
C10 C11 C12 . . 119.8(7) ?
C10 C11 H11 . . 120.1 ?
C12 C11 H11 . . 120.1 ?
C13 C12 C11 . . 119.7(7) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C8 . . 119.0(6) ?
C12 C13 C14 . . 132.3(7) ?
C8 C13 C14 . . 108.6(6) ?
O2 C14 C13 . . 115.8(6) ?
O2 C14 C16 . . 109.1(6) ?
C13 C14 C16 . . 113.2(6) ?
O2 C14 C15 . . 106.4(5) ?
C13 C14 C15 . . 102.3(6) ?
C16 C14 C15 . . 109.6(6) ?
O1 C15 N1 . . 124.8(7) ?
O1 C15 C14 . . 127.2(7) ?
N1 C15 C14 . . 108.0(6) ?
O3 C16 C14 . . 108.5(6) ?
O3 C16 H16A . . 110.0 ?
C14 C16 H16A . . 110.0 ?
O3 C16 H16B . . 110.0 ?
C14 C16 H16B . . 110.0 ?
H16A C16 H16B . . 108.4 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.6(14) ?
C1 C2 C3 C4 . . . . 1.4(16) ?
C2 C3 C4 C5 . . . . -0.7(16) ?
C3 C4 C5 C6 . . . . -0.9(14) ?
C2 C1 C6 C5 . . . . -1.0(12) ?
C2 C1 C6 C7 . . . . 176.6(7) ?
C4 C5 C6 C1 . . . . 1.7(12) ?
C4 C5 C6 C7 . . . . -175.9(7) ?
C15 N1 C7 C6 . . . . -109.6(7) ?
C8 N1 C7 C6 . . . . 72.1(8) ?
C1 C6 C7 N1 . . . . 51.2(9) ?
C5 C6 C7 N1 . . . . -131.2(7) ?
C15 N1 C8 C9 . . . . -178.9(7) ?
C7 N1 C8 C9 . . . . -0.4(11) ?
C15 N1 C8 C13 . . . . 0.3(8) ?
C7 N1 C8 C13 . . . . 178.8(6) ?
C13 C8 C9 C10 . . . . 1.1(11) ?
N1 C8 C9 C10 . . . . -179.8(7) ?
C8 C9 C10 C11 . . . . 0.3(11) ?
C8 C9 C10 Cl1 . . . . -179.1(6) ?
C9 C10 C11 C12 . . . . -1.3(12) ?
Cl1 C10 C11 C12 . . . . 178.1(6) ?
C10 C11 C12 C13 . . . . 0.9(12) ?
C11 C12 C13 C8 . . . . 0.5(11) ?
C11 C12 C13 C14 . . . . -174.8(7) ?
C9 C8 C13 C12 . . . . -1.5(11) ?
N1 C8 C13 C12 . . . . 179.2(6) ?
C9 C8 C13 C14 . . . . 174.8(7) ?
N1 C8 C13 C14 . . . . -4.5(8) ?
C12 C13 C14 O2 . . . . -62.8(11) ?
C8 C13 C14 O2 . . . . 121.5(6) ?
C12 C13 C14 C16 . . . . 64.2(10) ?
C8 C13 C14 C16 . . . . -111.5(7) ?
C12 C13 C14 C15 . . . . -178.0(8) ?
C8 C13 C14 C15 . . . . 6.3(7) ?
C8 N1 C15 O1 . . . . -176.1(6) ?
C7 N1 C15 O1 . . . . 5.4(11) ?
C8 N1 C15 C14 . . . . 3.9(7) ?
C7 N1 C15 C14 . . . . -174.6(6) ?
O2 C14 C15 O1 . . . . 52.0(9) ?
C13 C14 C15 O1 . . . . 173.8(7) ?
C16 C14 C15 O1 . . . . -65.8(9) ?
O2 C14 C15 N1 . . . . -128.0(6) ?
C13 C14 C15 N1 . . . . -6.1(7) ?
C16 C14 C15 N1 . . . . 114.2(6) ?
O2 C14 C16 O3 . . . . -168.8(5) ?
C13 C14 C16 O3 . . . . 60.7(7) ?
C15 C14 C16 O3 . . . . -52.7(7) ?

####################################################################### 
# 
# 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_2B
_database_code_depnum_ccdc_archive 'CCDC 1961236'
loop_
_audit_author_name
_audit_author_address
'Dr. E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         193.20

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.3175(11)
_cell_length_b                   10.2481(16)
_cell_length_c                   10.9658(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.059(5)
_cell_angle_gamma                90
_cell_volume                     925.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6982
_cell_measurement_theta_min      3.1734
_cell_measurement_theta_max      28.2036
_cell_measurement_temperature    122.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.225
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'


_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9770

_exptl_special_details           
;
;

_diffrn_ambient_temperature      122.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11988
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_full        28.55
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2254
_reflns_number_gt                1811
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_gt          0.1858
_refine_ls_wR_factor_ref         0.1953
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_number_reflns         2254
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0834P)²+0.4936P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9502(2) 0.36102(19) 0.43044(18) 0.0668(6) Uani d . . . 1 . .
O O2 0.8396(2) 0.41773(17) 0.17009(16) 0.0506(5) Uani d . . . 1 . .
O O3 0.8067(2) 0.67865(15) 0.38409(16) 0.0457(4) Uani d . . . 1 . .
N N1 0.6751(3) 0.36164(17) 0.42755(17) 0.0479(5) Uani d . . . 1 . .
C C1 0.5928(2) 0.4783(2) 0.25349(19) 0.0394(5) Uani d . . . 1 . .
C C2 0.4816(3) 0.5333(3) 0.1648(3) 0.0560(6) Uani d . . . 1 . .
C C3 0.3186(4) 0.5152(4) 0.1705(4) 0.0767(10) Uani d . . . 1 . .
C C4 0.2695(4) 0.4436(4) 0.2630(4) 0.0796(11) Uani d . . . 1 . .
C C5 0.3784(4) 0.3901(3) 0.3546(3) 0.0677(9) Uani d . . . 1 . .
C C6 0.5409(3) 0.4087(2) 0.3483(2) 0.0439(5) Uani d . . . 1 . .
C C7 0.8143(3) 0.39321(19) 0.3858(2) 0.0433(5) Uani d . . . 1 . .
C C8 0.7741(2) 0.47492(19) 0.26905(19) 0.0376(5) Uani d . . . 1 . .
C C9 0.6646(5) 0.2787(3) 0.5328(3) 0.0794(11) Uani d . . . 1 . .
H H9A 0.611067 0.196581 0.505115 0.119 Uiso calc U . R 1 . .
H H9B 0.601432 0.3229 0.589587 0.119 Uiso calc U . R 1 . .
H H9C 0.77403 0.260404 0.575 0.119 Uiso calc U . R 1 . .
C C10 0.8544(3) 0.6083(2) 0.2850(2) 0.0454(5) Uani d . . . 1 . .
H H2 0.516(4) 0.577(3) 0.102(3) 0.068(9) Uiso d . . . 1 . .
H H3 0.241(5) 0.552(4) 0.115(4) 0.100(13) Uiso d . . . 1 . .
H H4 0.158(5) 0.429(4) 0.263(4) 0.105(13) Uiso d . . . 1 . .
H H3C 0.875(4) 0.669(3) 0.445(3) 0.067(9) Uiso d . . . 1 . .
H H5 0.350(4) 0.343(4) 0.415(3) 0.080(10) Uiso d . . . 1 . .
H H10A 0.818(3) 0.657(3) 0.205(3) 0.054(7) Uiso d . . . 1 . .
H H10B 0.973(4) 0.594(3) 0.297(3) 0.062(8) Uiso d . . . 1 . .
H H2CC 0.789(4) 0.341(3) 0.143(3) 0.065(8) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.214(3) ?
O2 C8 . 1.408(2) ?
O2 H2CC . 0.92(3) ?
O3 C10 . 1.406(3) ?
O3 H3C . 0.82(4) ?
N1 C7 . 1.343(3) ?
N1 C6 . 1.401(3) ?
N1 C9 . 1.446(3) ?
C1 C2 . 1.366(3) ?
C1 C6 . 1.379(3) ?
C1 C8 . 1.494(3) ?
C2 C3 . 1.379(5) ?
C2 H2 . 0.90(3) ?
C3 C4 . 1.361(6) ?
C3 H3 . 0.91(4) ?
C4 C5 . 1.369(6) ?
C4 H4 . 0.94(4) ?
C5 C6 . 1.376(3) ?
C5 H5 . 0.88(4) ?
C7 C8 . 1.527(3) ?
C8 C10 . 1.521(3) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 1.02(3) ?
C10 H10B . 0.99(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 O2 H2CC . . 113.5(19) ?
C10 O3 H3C . . 109.(2) ?
C7 N1 C6 . . 110.84(18) ?
C7 N1 C9 . . 124.4(2) ?
C6 N1 C9 . . 124.4(2) ?
C2 C1 C6 . . 119.9(2) ?
C2 C1 C8 . . 131.5(2) ?
C6 C1 C8 . . 108.65(19) ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2 . . 119.(2) ?
C3 C2 H2 . . 122.(2) ?
C4 C3 C2 . . 120.4(3) ?
C4 C3 H3 . . 118.(3) ?
C2 C3 H3 . . 122.(3) ?
C3 C4 C5 . . 121.7(3) ?
C3 C4 H4 . . 119.(3) ?
C5 C4 H4 . . 119.(3) ?
C4 C5 C6 . . 117.5(3) ?
C4 C5 H5 . . 123.(2) ?
C6 C5 H5 . . 119.(2) ?
C5 C6 C1 . . 121.5(3) ?
C5 C6 N1 . . 128.6(3) ?
C1 C6 N1 . . 109.82(19) ?
O1 C7 N1 . . 126.6(2) ?
O1 C7 C8 . . 124.7(2) ?
N1 C7 C8 . . 108.68(19) ?
O2 C8 C1 . . 114.51(17) ?
O2 C8 C10 . . 104.59(17) ?
C1 C8 C10 . . 114.35(17) ?
O2 C8 C7 . . 110.79(17) ?
C1 C8 C7 . . 101.94(17) ?
C10 C8 C7 . . 110.82(18) ?
N1 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
N1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O3 C10 C8 . . 112.52(18) ?
O3 C10 H10A . . 109.6(15) ?
C8 C10 H10A . . 105.4(15) ?
O3 C10 H10B . . 111.1(18) ?
C8 C10 H10B . . 107.0(17) ?
H10A C10 H10B . . 111.(2) ?

####################################################################### 
# 
# 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_2E
_database_code_depnum_ccdc_archive 'CCDC 1961237'
loop_
_audit_author_name
_audit_author_address
'Dr. E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         299.31
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   8.4593(5)
_cell_length_b                   5.8691(4)
_cell_length_c                   30.718(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.420(2)
_cell_angle_gamma                90
_cell_volume                     1512.33(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8889
_cell_measurement_theta_min      2.4337
_cell_measurement_theta_max      24.0465
_cell_measurement_temperature    305.(2)

_exptl_crystal_description       ROD
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.607
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.106
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'


_exptl_absorpt_correction_T_min  0.9450
_exptl_absorpt_correction_T_max  0.9900

_exptl_special_details           
;
;

_diffrn_ambient_temperature      305.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            22546
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38

_refine_special_details          
;
;

_reflns_number_total             5901
_reflns_number_gt                4746
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1430
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         5901
_refine_ls_number_parameters     469
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+0.2273P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.175
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1798 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.0422(5) -0.4630(6) 0.39072(13) 0.0743(10) Uani d . . . 1 . .
O O2 0.1478(4) -0.2327(7) 0.47589(11) 0.0664(9) Uani d . . . 1 . .
H H2A 0.256(9) -0.280(11) 0.4882(14) 0.1 Uiso calc U . R 1 . .
O O3 -0.0218(4) 0.0901(6) 0.38199(12) 0.0609(8) Uani d . . . 1 . .
O O4 0.5802(4) 0.4421(6) 0.46070(12) 0.0660(9) Uani d . . . 1 . .
O O5 0.4121(5) 0.3514(5) 0.61093(13) 0.0726(10) Uani d . . . 1 . .
O O6 0.4218(4) 0.5911(6) 0.52646(10) 0.0571(8) Uani d . . . 1 . .
H H6 0.498(7) 0.567(11) 0.5136(14) 0.086 Uiso calc U . R 1 . .
O O7 0.3560(4) 0.9051(6) 0.62246(11) 0.0619(8) Uani d . . . 1 . .
H H7 0.398(8) 1.066(12) 0.6238(3) 0.093 Uiso calc U . R 1 . .
O O8 0.8668(5) 1.2649(7) 0.53753(14) 0.0829(12) Uani d . . . 1 . .
N N1 0.2699(5) -0.2884(6) 0.37504(12) 0.0517(8) Uani d . . . 1 . .
N N2 0.6517(5) 0.5344(6) 0.62604(12) 0.0527(9) Uani d . . . 1 . .
C C1 0.1765(7) -0.0985(9) 0.28897(18) 0.0668(13) Uani d . . . 1 . .
C C2 0.1487(8) 0.0128(13) 0.2492(2) 0.0834(17) Uani d . . . 1 . .
H H2 0.08926 0.146527 0.246788 0.1 Uiso calc U . R 1 . .
C C3 0.2072(9) -0.0710(17) 0.2139(2) 0.102(2) Uani d . . . 1 . .
H H3 0.189359 0.00506 0.187106 0.122 Uiso calc U . R 1 . .
C C4 0.2944(10) -0.2719(17) 0.2175(2) 0.111(3) Uani d . . . 1 . .
H H4 0.332547 -0.33198 0.192871 0.134 Uiso calc U . R 1 . .
C C5 0.3257(8) -0.3851(14) 0.2577(2) 0.0852(18) Uani d . . . 1 . .
C C6 0.2658(6) -0.2951(8) 0.29374(16) 0.0569(11) Uani d . . . 1 . .
C C7 0.2981(7) -0.4225(8) 0.33707(17) 0.0665(13) Uani d . . . 1 . .
H H7A 0.230902 -0.556857 0.335614 0.08 Uiso calc U . R 1 . .
H H7B 0.408165 -0.473324 0.341008 0.08 Uiso calc U . R 1 . .
C C8 0.3670(5) -0.1025(7) 0.39200(13) 0.0438(9) Uani d . . . 1 . .
C C9 0.5038(5) -0.0191(8) 0.37854(17) 0.0546(11) Uani d . . . 1 . .
C C10 0.5787(5) 0.1648(8) 0.40115(16) 0.0526(10) Uani d . . . 1 . .
C C11 0.5141(5) 0.2596(7) 0.43611(14) 0.0447(9) Uani d . . . 1 . .
C C12 0.3742(5) 0.1747(7) 0.44954(14) 0.0455(9) Uani d . . . 1 . .
C C13 0.3018(5) -0.0073(7) 0.42712(13) 0.0431(8) Uani d . . . 1 . .
C C14 0.1520(5) -0.1340(7) 0.43348(14) 0.0467(9) Uani d . . . 1 . .
C C15 0.1453(5) -0.3163(7) 0.39801(15) 0.0528(11) Uani d . . . 1 . .
C C16 0.7230(6) 0.5377(10) 0.4485(2) 0.0718(15) Uani d . . . 1 . .
H H16A 0.702183 0.598925 0.419316 0.108 Uiso calc U . R 1 . .
H H16B 0.803142 0.421381 0.449245 0.108 Uiso calc U . R 1 . .
H H16C 0.759916 0.657072 0.468618 0.108 Uiso calc U . R 1 . .
C C17 0.0031(5) 0.0133(9) 0.42532(17) 0.0555(11) Uani d . . . 1 . .
C C18 0.8228(8) 0.4465(14) 0.7432(2) 0.0866(18) Uani d . . . 1 . .
C C19 0.8297(10) 0.5615(18) 0.7830(2) 0.112(3) Uani d . . . 1 . .
H H19 0.893162 0.503135 0.807477 0.134 Uiso calc U . R 1 . .
C C20 0.7464(8) 0.7564(17) 0.7873(2) 0.097(2) Uani d . . . 1 . .
C C21 0.6510(8) 0.8404(13) 0.7515(2) 0.0826(17) Uani d . . . 1 . .
C C22 0.6403(7) 0.7279(9) 0.71135(19) 0.0672(13) Uani d . . . 1 . .
C C23 0.7276(6) 0.5328(8) 0.70702(16) 0.0580(11) Uani d . . . 1 . .
C C24 0.7182(9) 0.4027(9) 0.66371(19) 0.0685(14) Uani d . . . 1 . .
C C25 0.7305(5) 0.7199(7) 0.60819(14) 0.0468(9) Uani d . . . 1 . .
C C26 0.8782(6) 0.8079(9) 0.62089(17) 0.0581(11) Uani d . . . 1 . .
C C27 0.9284(6) 0.9911(8) 0.59678(17) 0.0591(11) Uani d . . . 1 . .
H H27 1.029548 1.052412 0.604441 0.071 Uiso calc U . R 1 . .
C C28 0.8297(5) 1.0813(8) 0.56194(16) 0.0556(11) Uani d . . . 1 . .
C C29 0.6796(6) 0.9912(8) 0.54985(15) 0.0509(10) Uani d . . . 1 . .
C C30 0.6298(5) 0.8109(6) 0.57300(13) 0.0422(8) Uani d . . . 1 . .
C C31 0.4750(5) 0.6845(7) 0.56869(14) 0.0451(9) Uani d . . . 1 . .
C C32 0.5059(6) 0.4988(6) 0.60405(15) 0.0503(10) Uani d . . . 1 . .
C C33 1.0208(8) 1.3604(12) 0.5467(2) 0.090(2) Uani d . . . 1 . .
H H33A 1.098744 1.251061 0.540185 0.135 Uiso calc U . R 1 . .
H H33B 1.040483 1.401147 0.577216 0.135 Uiso calc U . R 1 . .
H H33C 1.027738 1.49398 0.529037 0.135 Uiso calc U . R 1 . .
C C34 0.3347(5) 0.8313(7) 0.57919(15) 0.0513(10) Uani d . . . 1 . .
H H34A 0.323907 0.962459 0.559818 0.062 Uiso calc U . R 1 . .
H H34B 0.237033 0.743326 0.573854 0.062 Uiso calc U . R 1 . .
H H1 0.136(6) -0.027(9) 0.3164(18) 0.059(13) Uiso d . . . 1 . .
H H3A 0.029(8) 0.234(11) 0.382(2) 0.087(18) Uiso d . . . 1 . .
H H5 0.387(8) -0.497(12) 0.260(2) 0.09(2) Uiso d . . . 1 . .
H H9 0.541(6) -0.072(9) 0.3545(18) 0.059(14) Uiso d . . . 1 . .
H H10 0.678(6) 0.238(9) 0.3955(16) 0.063(14) Uiso d . . . 1 . .
H H12 0.332(5) 0.247(7) 0.4741(15) 0.043(10) Uiso d . . . 1 . .
H H18 0.870(8) 0.322(11) 0.742(2) 0.074(18) Uiso d . . . 1 . .
H H17A 0.023(6) 0.146(10) 0.4462(18) 0.064(14) Uiso d . . . 1 . .
H H17B -0.084(6) -0.077(8) 0.4336(16) 0.056(13) Uiso d . . . 1 . .
H H20 0.750(8) 0.822(11) 0.816(3) 0.10(2) Uiso d . . . 1 . .
H H21 0.593(8) 0.997(12) 0.754(2) 0.090(19) Uiso d . . . 1 . .
H H22 0.582(7) 0.814(10) 0.688(2) 0.075(16) Uiso d . . . 1 . .
H H24A 0.655(8) 0.281(12) 0.665(2) 0.088(19) Uiso d . . . 1 . .
H H24B 0.831(8) 0.352(10) 0.6633(19) 0.075(17) Uiso d . . . 1 . .
H H26 0.953(6) 0.761(8) 0.6451(16) 0.050(12) Uiso d . . . 1 . .
H H29 0.610(6) 1.055(9) 0.5312(18) 0.057(14) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 . 1.225(5) ?
O2 C14 . 1.430(5) ?
O2 H2A . 0.99(8) ?
O3 C17 . 1.395(6) ?
O3 H3A . 0.95(7) ?
O4 C11 . 1.386(5) ?
O4 C16 . 1.426(5) ?
O5 C32 . 1.211(5) ?
O6 C31 . 1.427(5) ?
O6 H6 . 0.81(7) ?
O7 C34 . 1.387(6) ?
O7 H7 . 1.01(7) ?
O8 C28 . 1.372(6) ?
O8 C33 . 1.413(7) ?
N1 C15 . 1.352(6) ?
N1 C8 . 1.423(5) ?
N1 C7 . 1.452(6) ?
N2 C32 . 1.344(6) ?
N2 C25 . 1.423(6) ?
N2 C24 . 1.444(7) ?
C1 C6 . 1.377(8) ?
C1 C2 . 1.380(8) ?
C1 H1 . 1.04(5) ?
C2 C3 . 1.342(10) ?
C2 H2 . 0.93 ?
C3 C4 . 1.388(12) ?
C3 H3 . 0.93 ?
C4 C5 . 1.396(11) ?
C4 H4 . 0.93 ?
C5 C6 . 1.381(7) ?
C5 H5 . 0.83(7) ?
C6 C7 . 1.520(7) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.369(6) ?
C8 C13 . 1.391(6) ?
C9 C10 . 1.391(7) ?
C9 H9 . 0.89(5) ?
C10 C11 . 1.383(6) ?
C10 H10 . 0.98(5) ?
C11 C12 . 1.395(5) ?
C12 C13 . 1.372(6) ?
C12 H12 . 0.97(5) ?
C13 C14 . 1.503(5) ?
C14 C17 . 1.521(7) ?
C14 C15 . 1.523(6) ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 1.01(6) ?
C17 H17B . 0.97(5) ?
C18 C23 . 1.383(8) ?
C18 C19 . 1.392(11) ?
C18 H18 . 0.83(7) ?
C19 C20 . 1.359(12) ?
C19 H19 . 0.93 ?
C20 C21 . 1.369(10) ?
C20 H20 . 0.96(7) ?
C21 C22 . 1.393(8) ?
C21 H21 . 1.05(7) ?
C22 C23 . 1.378(7) ?
C22 H22 . 0.96(6) ?
C23 C24 . 1.527(8) ?
C24 H24A . 0.89(7) ?
C24 H24B . 1.00(6) ?
C25 C26 . 1.362(7) ?
C25 C30 . 1.393(6) ?
C26 C27 . 1.402(7) ?
C26 H26 . 0.95(5) ?
C27 C28 . 1.376(7) ?
C27 H27 . 0.93 ?
C28 C29 . 1.382(6) ?
C29 C30 . 1.371(6) ?
C29 H29 . 0.85(5) ?
C30 C31 . 1.496(5) ?
C31 C34 . 1.534(6) ?
C31 C32 . 1.537(6) ?
C33 H33A . 0.96 ?
C33 H33B . 0.96 ?
C33 H33C . 0.96 ?
C34 H34A . 0.97 ?
C34 H34B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O2 H2A . . 109.5 ?
C17 O3 H3A . . 106.(4) ?
C11 O4 C16 . . 117.1(4) ?
C31 O6 H6 . . 109.5 ?
C34 O7 H7 . . 109.5 ?
C28 O8 C33 . . 118.2(5) ?
C15 N1 C8 . . 110.7(3) ?
C15 N1 C7 . . 125.0(4) ?
C8 N1 C7 . . 124.2(4) ?
C32 N2 C25 . . 111.7(4) ?
C32 N2 C24 . . 123.9(4) ?
C25 N2 C24 . . 124.4(5) ?
C6 C1 C2 . . 121.3(6) ?
C6 C1 H1 . . 119.(3) ?
C2 C1 H1 . . 119.(3) ?
C3 C2 C1 . . 120.3(7) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C2 C3 C4 . . 119.5(6) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.0(6) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C6 C5 C4 . . 118.6(7) ?
C6 C5 H5 . . 121.(5) ?
C4 C5 H5 . . 120.(5) ?
C1 C6 C5 . . 119.2(6) ?
C1 C6 C7 . . 122.6(4) ?
C5 C6 C7 . . 118.1(5) ?
N1 C7 C6 . . 114.0(4) ?
N1 C7 H7A . . 108.7 ?
C6 C7 H7A . . 108.7 ?
N1 C7 H7B . . 108.7 ?
C6 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C9 C8 C13 . . 121.7(4) ?
C9 C8 N1 . . 129.4(4) ?
C13 C8 N1 . . 108.9(3) ?
C8 C9 C10 . . 118.4(4) ?
C8 C9 H9 . . 122.(3) ?
C10 C9 H9 . . 120.(3) ?
C11 C10 C9 . . 120.0(4) ?
C11 C10 H10 . . 113.(3) ?
C9 C10 H10 . . 127.(3) ?
C10 C11 O4 . . 124.2(4) ?
C10 C11 C12 . . 121.4(4) ?
O4 C11 C12 . . 114.4(4) ?
C13 C12 C11 . . 118.1(4) ?
C13 C12 H12 . . 123.(3) ?
C11 C12 H12 . . 119.(3) ?
C12 C13 C8 . . 120.4(4) ?
C12 C13 C14 . . 130.5(4) ?
C8 C13 C14 . . 109.1(3) ?
O2 C14 C13 . . 116.0(4) ?
O2 C14 C17 . . 105.2(3) ?
C13 C14 C17 . . 113.0(3) ?
O2 C14 C15 . . 111.4(3) ?
C13 C14 C15 . . 102.0(3) ?
C17 C14 C15 . . 109.2(4) ?
O1 C15 N1 . . 125.0(4) ?
O1 C15 C14 . . 125.7(4) ?
N1 C15 C14 . . 109.2(3) ?
O4 C16 H16A . . 109.5 ?
O4 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O4 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O3 C17 C14 . . 111.1(4) ?
O3 C17 H17A . . 111.(3) ?
C14 C17 H17A . . 105.(3) ?
O3 C17 H17B . . 114.(3) ?
C14 C17 H17B . . 107.(3) ?
H17A C17 H17B . . 109.(4) ?
C23 C18 C19 . . 118.9(7) ?
C23 C18 H18 . . 122.(5) ?
C19 C18 H18 . . 119.(4) ?
C20 C19 C18 . . 122.0(6) ?
C20 C19 H19 . . 119.0 ?
C18 C19 H19 . . 119.0 ?
C19 C20 C21 . . 119.0(7) ?
C19 C20 H20 . . 118.(4) ?
C21 C20 H20 . . 123.(4) ?
C20 C21 C22 . . 120.3(7) ?
C20 C21 H21 . . 119.(4) ?
C22 C21 H21 . . 120.(4) ?
C23 C22 C21 . . 120.3(6) ?
C23 C22 H22 . . 127.(4) ?
C21 C22 H22 . . 112.(4) ?
C22 C23 C18 . . 119.4(6) ?
C22 C23 C24 . . 122.1(5) ?
C18 C23 C24 . . 118.5(5) ?
N2 C24 C23 . . 113.7(4) ?
N2 C24 H24A . . 106.(4) ?
C23 C24 H24A . . 110.(4) ?
N2 C24 H24B . . 115.(3) ?
C23 C24 H24B . . 102.(3) ?
H24A C24 H24B . . 110.(5) ?
C26 C25 C30 . . 121.5(4) ?
C26 C25 N2 . . 129.6(4) ?
C30 C25 N2 . . 108.8(4) ?
C25 C26 C27 . . 117.9(4) ?
C25 C26 H26 . . 127.(3) ?
C27 C26 H26 . . 115.(3) ?
C28 C27 C26 . . 120.7(4) ?
C28 C27 H27 . . 119.6 ?
C26 C27 H27 . . 119.6 ?
O8 C28 C27 . . 124.6(4) ?
O8 C28 C29 . . 114.9(4) ?
C27 C28 C29 . . 120.4(4) ?
C30 C29 C28 . . 119.3(4) ?
C30 C29 H29 . . 117.(4) ?
C28 C29 H29 . . 123.(4) ?
C29 C30 C25 . . 120.1(4) ?
C29 C30 C31 . . 131.3(4) ?
C25 C30 C31 . . 108.6(3) ?
O6 C31 C30 . . 116.2(3) ?
O6 C31 C34 . . 104.2(3) ?
C30 C31 C34 . . 113.3(3) ?
O6 C31 C32 . . 112.0(3) ?
C30 C31 C32 . . 102.8(3) ?
C34 C31 C32 . . 108.4(3) ?
O5 C32 N2 . . 127.1(5) ?
O5 C32 C31 . . 125.1(5) ?
N2 C32 C31 . . 107.8(3) ?
O8 C33 H33A . . 109.5 ?
O8 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
O8 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
O7 C34 C31 . . 111.6(4) ?
O7 C34 H34A . . 109.3 ?
C31 C34 H34A . . 109.3 ?
O7 C34 H34B . . 109.3 ?
C31 C34 H34B . . 109.3 ?
H34A C34 H34B . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.9(10) ?
C1 C2 C3 C4 . . . . 0.7(11) ?
C2 C3 C4 C5 . . . . -1.6(13) ?
C3 C4 C5 C6 . . . . 1.0(12) ?
C2 C1 C6 C5 . . . . -1.5(9) ?
C2 C1 C6 C7 . . . . -179.8(5) ?
C4 C5 C6 C1 . . . . 0.5(10) ?
C4 C5 C6 C7 . . . . 178.9(6) ?
C15 N1 C7 C6 . . . . 107.0(5) ?
C8 N1 C7 C6 . . . . -70.2(6) ?
C1 C6 C7 N1 . . . . -17.6(7) ?
C5 C6 C7 N1 . . . . 164.2(5) ?
C15 N1 C8 C9 . . . . 179.5(4) ?
C7 N1 C8 C9 . . . . -2.9(7) ?
C15 N1 C8 C13 . . . . -0.2(5) ?
C7 N1 C8 C13 . . . . 177.4(4) ?
C13 C8 C9 C10 . . . . 0.5(7) ?
N1 C8 C9 C10 . . . . -179.1(4) ?
C8 C9 C10 C11 . . . . -0.4(7) ?
C9 C10 C11 O4 . . . . 179.8(4) ?
C9 C10 C11 C12 . . . . 0.0(7) ?
C16 O4 C11 C10 . . . . 0.6(7) ?
C16 O4 C11 C12 . . . . -179.6(4) ?
C10 C11 C12 C13 . . . . 0.2(7) ?
O4 C11 C12 C13 . . . . -179.5(4) ?
C11 C12 C13 C8 . . . . -0.2(6) ?
C11 C12 C13 C14 . . . . -179.6(4) ?
C9 C8 C13 C12 . . . . -0.2(6) ?
N1 C8 C13 C12 . . . . 179.5(4) ?
C9 C8 C13 C14 . . . . 179.4(4) ?
N1 C8 C13 C14 . . . . -0.9(5) ?
C12 C13 C14 O2 . . . . -57.7(6) ?
C8 C13 C14 O2 . . . . 122.8(4) ?
C12 C13 C14 C17 . . . . 64.0(6) ?
C8 C13 C14 C17 . . . . -115.6(4) ?
C12 C13 C14 C15 . . . . -179.0(4) ?
C8 C13 C14 C15 . . . . 1.5(4) ?
C8 N1 C15 O1 . . . . 179.9(4) ?
C7 N1 C15 O1 . . . . 2.4(7) ?
C8 N1 C15 C14 . . . . 1.2(5) ?
C7 N1 C15 C14 . . . . -176.4(4) ?
O2 C14 C15 O1 . . . . 55.2(6) ?
C13 C14 C15 O1 . . . . 179.6(4) ?
C17 C14 C15 O1 . . . . -60.5(5) ?
O2 C14 C15 N1 . . . . -126.1(4) ?
C13 C14 C15 N1 . . . . -1.6(5) ?
C17 C14 C15 N1 . . . . 118.2(4) ?
O2 C14 C17 O3 . . . . -170.1(4) ?
C13 C14 C17 O3 . . . . 62.3(5) ?
C15 C14 C17 O3 . . . . -50.5(5) ?
C23 C18 C19 C20 . . . . -0.4(13) ?
C18 C19 C20 C21 . . . . 1.1(13) ?
C19 C20 C21 C22 . . . . -0.4(11) ?
C20 C21 C22 C23 . . . . -1.0(10) ?
C21 C22 C23 C18 . . . . 1.7(9) ?
C21 C22 C23 C24 . . . . 179.4(6) ?
C19 C18 C23 C22 . . . . -1.0(10) ?
C19 C18 C23 C24 . . . . -178.8(7) ?
C32 N2 C24 C23 . . . . -107.8(6) ?
C25 N2 C24 C23 . . . . 70.8(7) ?
C22 C23 C24 N2 . . . . 17.8(8) ?
C18 C23 C24 N2 . . . . -164.5(6) ?
C32 N2 C25 C26 . . . . -179.7(4) ?
C24 N2 C25 C26 . . . . 1.5(7) ?
C32 N2 C25 C30 . . . . 0.6(5) ?
C24 N2 C25 C30 . . . . -178.2(4) ?
C30 C25 C26 C27 . . . . -1.4(7) ?
N2 C25 C26 C27 . . . . 178.9(4) ?
C25 C26 C27 C28 . . . . 1.2(7) ?
C33 O8 C28 C27 . . . . 4.3(8) ?
C33 O8 C28 C29 . . . . -177.4(5) ?
C26 C27 C28 O8 . . . . 177.7(5) ?
C26 C27 C28 C29 . . . . -0.6(8) ?
O8 C28 C29 C30 . . . . -178.3(4) ?
C27 C28 C29 C30 . . . . 0.1(7) ?
C28 C29 C30 C25 . . . . -0.3(6) ?
C28 C29 C30 C31 . . . . 177.8(4) ?
C26 C25 C30 C29 . . . . 1.0(6) ?
N2 C25 C30 C29 . . . . -179.3(4) ?
C26 C25 C30 C31 . . . . -177.5(4) ?
N2 C25 C30 C31 . . . . 2.3(4) ?
C29 C30 C31 O6 . . . . 55.2(6) ?
C25 C30 C31 O6 . . . . -126.6(4) ?
C29 C30 C31 C34 . . . . -65.4(6) ?
C25 C30 C31 C34 . . . . 112.9(4) ?
C29 C30 C31 C32 . . . . 177.9(4) ?
C25 C30 C31 C32 . . . . -3.9(4) ?
C25 N2 C32 O5 . . . . 178.5(4) ?
C24 N2 C32 O5 . . . . -2.7(7) ?
C25 N2 C32 C31 . . . . -3.1(5) ?
C24 N2 C32 C31 . . . . 175.7(4) ?
O6 C31 C32 O5 . . . . -51.9(6) ?
C30 C31 C32 O5 . . . . -177.4(4) ?
C34 C31 C32 O5 . . . . 62.5(5) ?
O6 C31 C32 N2 . . . . 129.6(4) ?
C30 C31 C32 N2 . . . . 4.2(4) ?
C34 C31 C32 N2 . . . . -116.0(4) ?
O6 C31 C34 O7 . . . . 170.0(3) ?
C30 C31 C34 O7 . . . . -62.9(5) ?
C32 C31 C34 O7 . . . . 50.5(4) ?

####################################################################### 
# 
# 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_2A
_database_code_depnum_ccdc_archive 'CCDC 1961235'
loop_
_audit_author_name
_audit_author_address
'Dr. E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-10-24 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C128 H120 N8 O24'
_chemical_formula_iupac          ?
_chemical_formula_weight         2154.31
_chemical_absolute_configuration ?

_chemical_melting_point          ?

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

_cell_length_a                   5.1638(3)
_cell_length_b                   19.3060(12)
_cell_length_c                   27.209(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2712.5(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1894
_cell_measurement_theta_min      2.4811
_cell_measurement_theta_max      20.1000
_cell_measurement_temperature    301.(2)

_exptl_crystal_description       ROD
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.448
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136

_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'


_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_T_max  0.9950

_exptl_special_details           
;
;

_diffrn_ambient_temperature      301.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            20795
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_unetI/netI     0.1510
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35

_refine_special_details          
;
;

_reflns_number_total             6671
_reflns_number_gt                2692
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2041
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1476
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_number_reflns         6671
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 713 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.8(10)

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5652(7) 0.42939(17) 0.57457(14) 0.0505(10) Uani d . . . 1 . .
O O2 1.0379(6) 0.39741(18) 0.52285(13) 0.0490(10) Uani d . . . 1 . .
H H2A 1.151(8) 0.378(3) 0.5032(13) 0.073 Uiso calc U . R 1 . .
O O3 0.4315(6) 0.3381(2) 0.46798(13) 0.0502(10) Uani d . . . 1 . .
H H3A 0.4369(8) 0.342(3) 0.440(2) 0.075 Uiso calc U . R 1 . .
O O4 0.4244(7) 0.34560(17) 0.36912(14) 0.0511(10) Uani d . . . 1 . .
O O5 0.9054(7) 0.27053(16) 0.36448(15) 0.0531(11) Uani d . . . 1 . .
H H5A 1.016(8) 0.243(2) 0.363(2) 0.08 Uiso calc U . R 1 . .
O O6 0.3071(6) 0.17248(18) 0.37042(14) 0.0505(11) Uani d . . . 1 . .
H H6A 0.259(5) 0.141(3) 0.3882(19) 0.076 Uiso calc U . R 1 . .
N N1 0.5248(7) 0.50107(19) 0.50821(16) 0.0422(11) Uani d . . . 1 . .
N N2 0.3960(8) 0.3006(2) 0.29194(17) 0.0510(12) Uani d . . . 1 . .
C C1 0.5974(13) 0.6196(3) 0.5794(3) 0.080(2) Uani d . . . 1 . .
H H1 0.692814 0.580636 0.588135 0.096 Uiso calc U . R 1 . .
C C2 0.6561(17) 0.6837(4) 0.5998(3) 0.105(3) Uani d . . . 1 . .
H H2 0.79196 0.687713 0.622022 0.125 Uiso calc U . R 1 . .
C C3 0.513(2) 0.7413(4) 0.5870(4) 0.117(4) Uani d . . . 1 . .
H H3 0.551768 0.784207 0.600802 0.141 Uiso calc U . R 1 . .
C C4 0.318(2) 0.7353(4) 0.5546(4) 0.122(3) Uani d . . . 1 . .
H H4 0.223044 0.774227 0.545701 0.147 Uiso calc U . R 1 . .
C C5 0.2575(13) 0.6720(3) 0.5343(3) 0.088(2) Uani d . . . 1 . .
H H5 0.12038 0.668518 0.512292 0.105 Uiso calc U . R 1 . .
C C6 0.3971(11) 0.6142(3) 0.5463(2) 0.0543(16) Uani d . . . 1 . .
C C7 0.3142(10) 0.5449(2) 0.5264(2) 0.0512(15) Uani d . . . 1 . .
H H7A 0.223358 0.520072 0.552155 0.061 Uiso calc U . R 1 . .
H H7B 0.192411 0.552569 0.499804 0.061 Uiso calc U . R 1 . .
C C8 0.6417(9) 0.5084(3) 0.4612(2) 0.0438(14) Uani d . . . 1 . .
C C9 0.6124(11) 0.5602(3) 0.4273(2) 0.0621(17) Uani d . . . 1 . .
H H9 0.49801 0.596646 0.432691 0.075 Uiso calc U . R 1 . .
C C10 0.7576(13) 0.5565(3) 0.3851(2) 0.076(2) Uani d . . . 1 . .
H H10 0.743231 0.59153 0.36174 0.091 Uiso calc U . R 1 . .
C C11 0.9240(13) 0.5021(3) 0.3766(2) 0.0698(18) Uani d . . . 1 . .
H H11 1.01851 0.500749 0.347544 0.084 Uiso calc U . R 1 . .
C C12 0.9532(11) 0.4492(3) 0.4108(2) 0.0554(15) Uani d . . . 1 . .
H H12 1.065261 0.412322 0.40504 0.066 Uiso calc U . R 1 . .
C C13 0.8102(10) 0.4531(2) 0.4536(2) 0.0412(13) Uani d . . . 1 . .
C C14 0.8003(9) 0.4060(2) 0.49762(19) 0.0413(13) Uani d . . . 1 . .
C C15 0.6188(9) 0.4453(3) 0.5328(2) 0.0429(13) Uani d . . . 1 . .
C C16 0.6881(9) 0.3342(2) 0.4870(2) 0.0446(14) Uani d . . . 1 . .
H H16A 0.798127 0.310526 0.463515 0.054 Uiso calc U . R 1 . .
H H16B 0.686967 0.307255 0.517121 0.054 Uiso calc U . R 1 . .
C C17 0.5231(15) 0.4454(4) 0.2609(3) 0.102(3) Uani d . . . 1 . .
H H17 0.584974 0.436196 0.292355 0.123 Uiso calc U . R 1 . .
C C18 0.629(2) 0.4981(4) 0.2345(4) 0.149(4) Uani d . . . 1 . .
H H18 0.760857 0.52463 0.248117 0.179 Uiso calc U . R 1 . .
C C19 0.545(2) 0.5120(5) 0.1888(4) 0.121(4) Uani d . . . 1 . .
H H19 0.622479 0.547189 0.170638 0.145 Uiso calc U . R 1 . .
C C20 0.354(3) 0.4758(5) 0.1700(3) 0.134(4) Uani d . . . 1 . .
H H20 0.292475 0.486358 0.138745 0.161 Uiso calc U . R 1 . .
C C21 0.2439(19) 0.4217(4) 0.1966(3) 0.111(3) Uani d . . . 1 . .
H H21 0.110145 0.395931 0.182887 0.133 Uiso calc U . R 1 . .
C C22 0.3295(11) 0.4064(3) 0.2423(2) 0.0585(16) Uani d . . . 1 . .
C C23 0.2060(10) 0.3495(3) 0.2721(2) 0.0609(17) Uani d . . . 1 . .
H H23A 0.109521 0.369925 0.298998 0.073 Uiso calc U . R 1 . .
H H23B 0.084421 0.32452 0.251465 0.073 Uiso calc U . R 1 . .
C C24 0.5200(11) 0.2480(3) 0.2648(2) 0.0508(15) Uani d . . . 1 . .
C C25 0.4907(14) 0.2322(4) 0.2154(2) 0.076(2) Uani d . . . 1 . .
H H25 0.375919 0.256425 0.195456 0.092 Uiso calc U . R 1 . .
C C26 0.6410(17) 0.1785(4) 0.1972(3) 0.090(2) Uani d . . . 1 . .
H H26 0.62388 0.165838 0.164393 0.108 Uiso calc U . R 1 . .
C C27 0.8140(17) 0.1435(4) 0.2262(3) 0.099(3) Uani d . . . 1 . .
H H27 0.915967 0.108654 0.212607 0.119 Uiso calc U . R 1 . .
C C28 0.8378(12) 0.1597(3) 0.2757(3) 0.0715(19) Uani d . . . 1 . .
H H28 0.951861 0.135104 0.295592 0.086 Uiso calc U . R 1 . .
C C29 0.6909(11) 0.2125(3) 0.2949(2) 0.0492(15) Uani d . . . 1 . .
C C30 0.6717(9) 0.2414(3) 0.34586(19) 0.0424(13) Uani d . . . 1 . .
C C31 0.4845(10) 0.3023(3) 0.3386(2) 0.0450(14) Uani d . . . 1 . .
C C32 0.5653(9) 0.1921(2) 0.3836(2) 0.0459(14) Uani d . . . 1 . .
H H32A 0.674294 0.151286 0.385412 0.055 Uiso calc U . R 1 . .
H H32B 0.564645 0.214163 0.415621 0.055 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 . 1.211(6) ?
O2 C14 . 1.416(5) ?
O2 H2A . 0.88(5) ?
O3 C16 . 1.425(5) ?
O3 H3A . 0.77(6) ?
O4 C31 . 1.219(6) ?
O5 C30 . 1.425(6) ?
O5 H5A . 0.78(5) ?
O6 C32 . 1.432(5) ?
O6 H6A . 0.82(5) ?
N1 C15 . 1.356(6) ?
N1 C8 . 1.422(6) ?
N1 C7 . 1.464(6) ?
N2 C31 . 1.349(6) ?
N2 C24 . 1.410(6) ?
N2 C23 . 1.465(6) ?
C1 C6 . 1.376(8) ?
C1 C2 . 1.388(8) ?
C1 H1 . 0.93 ?
C2 C3 . 1.380(11) ?
C2 H2 . 0.93 ?
C3 C4 . 1.346(12) ?
C3 H3 . 0.93 ?
C4 C5 . 1.375(9) ?
C4 H4 . 0.93 ?
C5 C6 . 1.369(8) ?
C5 H5 . 0.93 ?
C6 C7 . 1.505(7) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 C9 . 1.368(7) ?
C8 C13 . 1.393(6) ?
C9 C10 . 1.374(8) ?
C9 H9 . 0.93 ?
C10 C11 . 1.377(8) ?
C10 H10 . 0.93 ?
C11 C12 . 1.390(7) ?
C11 H11 . 0.93 ?
C12 C13 . 1.380(7) ?
C12 H12 . 0.93 ?
C13 C14 . 1.506(7) ?
C14 C16 . 1.530(6) ?
C14 C15 . 1.539(7) ?
C16 H16A . 0.97 ?
C16 H16B . 0.97 ?
C17 C22 . 1.350(8) ?
C17 C18 . 1.360(10) ?
C17 H17 . 0.93 ?
C18 C19 . 1.341(12) ?
C18 H18 . 0.93 ?
C19 C20 . 1.314(12) ?
C19 H19 . 0.93 ?
C20 C21 . 1.394(10) ?
C20 H20 . 0.93 ?
C21 C22 . 1.352(8) ?
C21 H21 . 0.93 ?
C22 C23 . 1.507(7) ?
C23 H23A . 0.97 ?
C23 H23B . 0.97 ?
C24 C29 . 1.385(7) ?
C24 C25 . 1.388(8) ?
C25 C26 . 1.387(9) ?
C25 H25 . 0.93 ?
C26 C27 . 1.369(10) ?
C26 H26 . 0.93 ?
C27 C28 . 1.389(9) ?
C27 H27 . 0.93 ?
C28 C29 . 1.374(7) ?
C28 H28 . 0.93 ?
C29 C30 . 1.498(7) ?
C30 C32 . 1.503(6) ?
C30 C31 . 1.535(7) ?
C32 H32A . 0.97 ?
C32 H32B . 0.97 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 O2 H2A . . 109.5 ?
C16 O3 H3A . . 109.5 ?
C30 O5 H5A . . 109.5 ?
C32 O6 H6A . . 109.5 ?
C15 N1 C8 . . 111.8(4) ?
C15 N1 C7 . . 123.9(4) ?
C8 N1 C7 . . 124.2(4) ?
C31 N2 C24 . . 110.8(5) ?
C31 N2 C23 . . 124.0(5) ?
C24 N2 C23 . . 125.1(5) ?
C6 C1 C2 . . 119.6(7) ?
C6 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C3 C2 C1 . . 120.1(8) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 119.7(8) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 120.7(9) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C6 C5 C4 . . 120.6(8) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.3(6) ?
C5 C6 C7 . . 119.3(6) ?
C1 C6 C7 . . 121.2(5) ?
N1 C7 C6 . . 115.1(4) ?
N1 C7 H7A . . 108.5 ?
C6 C7 H7A . . 108.5 ?
N1 C7 H7B . . 108.5 ?
C6 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C9 C8 C13 . . 121.9(5) ?
C9 C8 N1 . . 129.2(5) ?
C13 C8 N1 . . 108.8(4) ?
C8 C9 C10 . . 117.7(5) ?
C8 C9 H9 . . 121.1 ?
C10 C9 H9 . . 121.1 ?
C9 C10 C11 . . 121.3(6) ?
C9 C10 H10 . . 119.3 ?
C11 C10 H10 . . 119.3 ?
C10 C11 C12 . . 121.2(6) ?
C10 C11 H11 . . 119.4 ?
C12 C11 H11 . . 119.4 ?
C13 C12 C11 . . 117.7(5) ?
C13 C12 H12 . . 121.2 ?
C11 C12 H12 . . 121.2 ?
C12 C13 C8 . . 120.2(5) ?
C12 C13 C14 . . 131.0(5) ?
C8 C13 C14 . . 108.9(5) ?
O2 C14 C13 . . 115.3(4) ?
O2 C14 C16 . . 108.3(4) ?
C13 C14 C16 . . 114.2(4) ?
O2 C14 C15 . . 106.5(4) ?
C13 C14 C15 . . 102.5(4) ?
C16 C14 C15 . . 109.5(4) ?
O1 C15 N1 . . 125.6(5) ?
O1 C15 C14 . . 126.7(5) ?
N1 C15 C14 . . 107.7(5) ?
O3 C16 C14 . . 111.9(4) ?
O3 C16 H16A . . 109.2 ?
C14 C16 H16A . . 109.2 ?
O3 C16 H16B . . 109.2 ?
C14 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C22 C17 C18 . . 121.0(8) ?
C22 C17 H17 . . 119.5 ?
C18 C17 H17 . . 119.5 ?
C19 C18 C17 . . 120.7(9) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C20 C19 C18 . . 119.8(9) ?
C20 C19 H19 . . 120.1 ?
C18 C19 H19 . . 120.1 ?
C19 C20 C21 . . 120.2(9) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C22 C21 C20 . . 120.6(8) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C17 C22 C21 . . 117.7(7) ?
C17 C22 C23 . . 121.3(6) ?
C21 C22 C23 . . 121.0(6) ?
N2 C23 C22 . . 112.6(4) ?
N2 C23 H23A . . 109.1 ?
C22 C23 H23A . . 109.1 ?
N2 C23 H23B . . 109.1 ?
C22 C23 H23B . . 109.1 ?
H23A C23 H23B . . 107.8 ?
C29 C24 C25 . . 122.2(6) ?
C29 C24 N2 . . 109.7(5) ?
C25 C24 N2 . . 128.0(6) ?
C26 C25 C24 . . 116.7(7) ?
C26 C25 H25 . . 121.7 ?
C24 C25 H25 . . 121.7 ?
C27 C26 C25 . . 121.9(7) ?
C27 C26 H26 . . 119.0 ?
C25 C26 H26 . . 119.0 ?
C26 C27 C28 . . 120.3(7) ?
C26 C27 H27 . . 119.8 ?
C28 C27 H27 . . 119.8 ?
C29 C28 C27 . . 119.2(7) ?
C29 C28 H28 . . 120.4 ?
C27 C28 H28 . . 120.4 ?
C28 C29 C24 . . 119.6(6) ?
C28 C29 C30 . . 131.7(6) ?
C24 C29 C30 . . 108.7(5) ?
O5 C30 C29 . . 114.8(4) ?
O5 C30 C32 . . 108.4(4) ?
C29 C30 C32 . . 114.9(4) ?
O5 C30 C31 . . 106.1(4) ?
C29 C30 C31 . . 102.0(5) ?
C32 C30 C31 . . 110.1(4) ?
O4 C31 N2 . . 124.9(5) ?
O4 C31 C30 . . 126.7(5) ?
N2 C31 C30 . . 108.4(5) ?
O6 C32 C30 . . 109.7(4) ?
O6 C32 H32A . . 109.7 ?
C30 C32 H32A . . 109.7 ?
O6 C32 H32B . . 109.7 ?
C30 C32 H32B . . 109.7 ?
H32A C32 H32B . . 108.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.4(12) ?
C1 C2 C3 C4 . . . . -0.4(14) ?
C2 C3 C4 C5 . . . . 0.7(15) ?
C3 C4 C5 C6 . . . . -0.9(14) ?
C4 C5 C6 C1 . . . . 0.9(11) ?
C4 C5 C6 C7 . . . . 175.6(7) ?
C2 C1 C6 C5 . . . . -0.6(10) ?
C2 C1 C6 C7 . . . . -175.2(6) ?
C15 N1 C7 C6 . . . . 104.6(6) ?
C8 N1 C7 C6 . . . . -80.4(6) ?
C5 C6 C7 N1 . . . . 136.7(6) ?
C1 C6 C7 N1 . . . . -48.7(8) ?
C15 N1 C8 C9 . . . . -174.9(5) ?
C7 N1 C8 C9 . . . . 9.6(8) ?
C15 N1 C8 C13 . . . . 3.1(5) ?
C7 N1 C8 C13 . . . . -172.4(4) ?
C13 C8 C9 C10 . . . . -0.6(9) ?
N1 C8 C9 C10 . . . . 177.2(5) ?
C8 C9 C10 C11 . . . . 1.1(9) ?
C9 C10 C11 C12 . . . . -0.7(10) ?
C10 C11 C12 C13 . . . . -0.2(9) ?
C11 C12 C13 C8 . . . . 0.6(8) ?
C11 C12 C13 C14 . . . . -178.8(5) ?
C9 C8 C13 C12 . . . . -0.2(8) ?
N1 C8 C13 C12 . . . . -178.4(5) ?
C9 C8 C13 C14 . . . . 179.3(5) ?
N1 C8 C13 C14 . . . . 1.1(5) ?
C12 C13 C14 O2 . . . . 60.0(7) ?
C8 C13 C14 O2 . . . . -119.4(5) ?
C12 C13 C14 C16 . . . . -66.4(7) ?
C8 C13 C14 C16 . . . . 114.2(5) ?
C12 C13 C14 C15 . . . . 175.3(5) ?
C8 C13 C14 C15 . . . . -4.2(5) ?
C8 N1 C15 O1 . . . . 175.2(5) ?
C7 N1 C15 O1 . . . . -9.3(8) ?
C8 N1 C15 C14 . . . . -5.8(5) ?
C7 N1 C15 C14 . . . . 169.7(4) ?
O2 C14 C15 O1 . . . . -53.5(7) ?
C13 C14 C15 O1 . . . . -175.0(5) ?
C16 C14 C15 O1 . . . . 63.3(6) ?
O2 C14 C15 N1 . . . . 127.5(4) ?
C13 C14 C15 N1 . . . . 6.0(5) ?
C16 C14 C15 N1 . . . . -115.7(4) ?
O2 C14 C16 O3 . . . . 171.6(4) ?
C13 C14 C16 O3 . . . . -58.4(6) ?
C15 C14 C16 O3 . . . . 55.9(6) ?
C22 C17 C18 C19 . . . . -0.7(15) ?
C17 C18 C19 C20 . . . . 1.9(17) ?
C18 C19 C20 C21 . . . . -2.0(16) ?
C19 C20 C21 C22 . . . . 0.9(15) ?
C18 C17 C22 C21 . . . . -0.4(12) ?
C18 C17 C22 C23 . . . . -178.1(7) ?
C20 C21 C22 C17 . . . . 0.3(12) ?
C20 C21 C22 C23 . . . . 178.1(7) ?
C31 N2 C23 C22 . . . . 99.7(6) ?
C24 N2 C23 C22 . . . . -77.1(6) ?
C17 C22 C23 N2 . . . . -53.0(8) ?
C21 C22 C23 N2 . . . . 129.3(7) ?
C31 N2 C24 C29 . . . . 1.7(6) ?
C23 N2 C24 C29 . . . . 178.9(4) ?
C31 N2 C24 C25 . . . . -176.7(6) ?
C23 N2 C24 C25 . . . . 0.5(8) ?
C29 C24 C25 C26 . . . . 0.3(9) ?
N2 C24 C25 C26 . . . . 178.5(5) ?
C24 C25 C26 C27 . . . . -1.3(10) ?
C25 C26 C27 C28 . . . . 2.1(12) ?
C26 C27 C28 C29 . . . . -1.7(11) ?
C27 C28 C29 C24 . . . . 0.7(9) ?
C27 C28 C29 C30 . . . . 179.5(6) ?
C25 C24 C29 C28 . . . . 0.0(8) ?
N2 C24 C29 C28 . . . . -178.5(5) ?
C25 C24 C29 C30 . . . . -179.0(5) ?
N2 C24 C29 C30 . . . . 2.5(6) ?
C28 C29 C30 O5 . . . . 61.9(8) ?
C24 C29 C30 O5 . . . . -119.2(5) ?
C28 C29 C30 C32 . . . . -64.9(8) ?
C24 C29 C30 C32 . . . . 114.0(5) ?
C28 C29 C30 C31 . . . . 176.1(6) ?
C24 C29 C30 C31 . . . . -5.0(5) ?
C24 N2 C31 O4 . . . . 174.8(5) ?
C23 N2 C31 O4 . . . . -2.5(8) ?
C24 N2 C31 C30 . . . . -5.0(5) ?
C23 N2 C31 C30 . . . . 177.8(4) ?
O5 C30 C31 O4 . . . . -53.1(6) ?
C29 C30 C31 O4 . . . . -173.7(5) ?
C32 C30 C31 O4 . . . . 64.0(6) ?
O5 C30 C31 N2 . . . . 126.6(4) ?
C29 C30 C31 N2 . . . . 6.1(5) ?
C32 C30 C31 N2 . . . . -116.3(5) ?
O5 C30 C32 O6 . . . . 168.7(4) ?
C29 C30 C32 O6 . . . . -61.3(6) ?
C31 C30 C32 O6 . . . . 53.1(6) ?

