# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SND59
_database_code_depnum_ccdc_archive 'CCDC 2105918'
loop_
_audit_author_name
_audit_author_address
'Dr. Pabitra Baran Chatterjee'
;Central Salt and Marine Chemicals Research Institute, Bhavnagar
India
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            INORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H42 Cu2 N6 O16'
_chemical_formula_iupac          ?
_chemical_formula_weight         869.77

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   6.5708(5)
_cell_length_b                   7.9441(6)
_cell_length_c                   17.2086(14)
_cell_angle_alpha                100.632(2)
_cell_angle_beta                 93.802(2)
_cell_angle_gamma                96.173(2)
_cell_volume                     874.32(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.4178
_cell_measurement_theta_max      30.5681
_cell_measurement_temperature    111.(2)

_exptl_crystal_description       ROD
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.074
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450

_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_correction_T_min  0.4900
_exptl_absorpt_correction_T_max  0.9100

_exptl_special_details           
;
;

_diffrn_ambient_temperature      111.(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            32888
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_full        30.59
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             5371
_reflns_number_gt                5078
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0605
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         5371
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0266P)²+0.4793P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.317
_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'
Cu Cu 0.3201 1.2651 '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
Cu Cu1 0.12887(2) 0.33843(2) 0.79785(2) 0.01260(4) Uani d . . . 1 . .
O O1 0.17372(14) 0.47546(11) 0.71817(5) 0.01617(16) Uani d . . . 1 . .
O O2 0.25920(13) 0.03331(10) 0.49982(5) 0.01385(15) Uani d . . . 1 . .
O O3 0.29156(14) -0.18151(11) 0.40214(5) 0.01729(16) Uani d . . . 1 . .
O O4 0.08418(14) 0.54654(11) 0.87595(5) 0.01644(16) Uani d . . . 1 . .
O O5 0.53349(14) 0.50231(11) 0.85342(6) 0.02182(18) Uani d . . . 1 . .
O O6 0.75483(14) 0.72996(12) 0.86241(6) 0.02358(19) Uani d . . . 1 . .
O O7 0.43943(14) 0.75790(12) 0.88499(6) 0.02352(19) Uani d . . . 1 . .
O O8 -0.22738(14) 0.27586(12) 0.76424(6) 0.01806(16) Uani d . . . 1 . .
N N1 0.21569(15) 0.13734(12) 0.73257(6) 0.01430(17) Uani d . . . 1 . .
N N2 0.11514(15) 0.19061(13) 0.88395(6) 0.01497(18) Uani d . . . 1 . .
N N3 0.57596(15) 0.66283(13) 0.86661(6) 0.01593(18) Uani d . . . 1 . .
C C1 0.20210(17) 0.42131(14) 0.64466(6) 0.01336(19) Uani d . . . 1 . .
C C2 0.21456(18) 0.54375(14) 0.59345(7) 0.0152(2) Uani d . . . 1 . .
C C3 0.24006(18) 0.49765(15) 0.51454(7) 0.0149(2) Uani d . . . 1 . .
C C4 0.25449(17) 0.32386(14) 0.47937(6) 0.01322(19) Uani d . . . 1 . .
C C5 0.27755(17) 0.26572(15) 0.39646(7) 0.01432(19) Uani d . . . 1 . .
C C6 0.29067(18) 0.09544(15) 0.36963(7) 0.0160(2) Uani d . . . 1 . .
C C7 0.28143(17) -0.02731(15) 0.42072(6) 0.01404(19) Uani d . . . 1 . .
C C8 0.24625(16) 0.20424(14) 0.52887(6) 0.01220(18) Uani d . . . 1 . .
C C9 0.22438(16) 0.24692(14) 0.61101(6) 0.01210(18) Uani d . . . 1 . .
C C10 0.23788(17) 0.11586(14) 0.65776(7) 0.01338(19) Uani d . . . 1 . .
C C11 0.2463(2) -0.00235(16) 0.77530(7) 0.0198(2) Uani d . . . 1 . .
C C12 0.0987(2) 0.01014(15) 0.83978(7) 0.0171(2) Uani d . . . 1 . .
C C13 0.3052(2) 0.23243(18) 0.93847(8) 0.0244(3) Uani d . . . 1 . .
C C14 -0.0633(2) 0.20952(19) 0.93150(8) 0.0247(3) Uani d . . . 1 . .
C C15 0.2847(2) 0.38897(16) 0.34056(7) 0.0183(2) Uani d . . . 1 . .
H H2 0.248(3) 0.581(2) 0.4836(11) 0.023(4) Uiso d . . . 1 . .
H H4 0.204(3) 0.662(2) 0.6138(11) 0.028(4) Uiso d . . . 1 . .
H H4C 0.189(3) 0.619(3) 0.8775(12) 0.041(6) Uiso d . . . 1 . .
H H4D -0.020(3) 0.590(3) 0.8664(12) 0.037(5) Uiso d . . . 1 . .
H H6 0.306(2) 0.052(2) 0.3143(10) 0.019(4) Uiso d . . . 1 . .
H H8C -0.290(3) 0.347(3) 0.7850(12) 0.032(5) Uiso d . . . 1 . .
H H8D -0.249(3) 0.263(2) 0.7182(12) 0.029(5) Uiso d . . . 1 . .
H H10 0.267(2) 0.009(2) 0.6323(10) 0.019(4) Uiso d . . . 1 . .
H H11A 0.394(3) 0.014(2) 0.7987(11) 0.025(4) Uiso d . . . 1 . .
H H11B 0.224(3) -0.108(2) 0.7415(11) 0.030(5) Uiso d . . . 1 . .
H H12A -0.042(3) -0.022(2) 0.8157(10) 0.019(4) Uiso d . . . 1 . .
H H12B 0.126(3) -0.063(2) 0.8766(10) 0.019(4) Uiso d . . . 1 . .
H H13A 0.306(3) 0.154(2) 0.9751(11) 0.028(4) Uiso d . . . 1 . .
H H13B 0.307(3) 0.349(2) 0.9653(11) 0.029(5) Uiso d . . . 1 . .
H H13C 0.421(3) 0.219(2) 0.9091(11) 0.028(5) Uiso d . . . 1 . .
H H14A -0.187(3) 0.178(2) 0.8957(12) 0.032(5) Uiso d . . . 1 . .
H H14B -0.058(3) 0.323(3) 0.9599(12) 0.035(5) Uiso d . . . 1 . .
H H14C -0.066(3) 0.130(2) 0.9667(10) 0.022(4) Uiso d . . . 1 . .
H H15A 0.153(3) 0.412(3) 0.3280(12) 0.038(5) Uiso d . . . 1 . .
H H15B 0.372(3) 0.495(2) 0.3632(11) 0.028(4) Uiso d . . . 1 . .
H H15C 0.339(4) 0.341(3) 0.2943(14) 0.053(6) 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
Cu1 O1 . 1.9202(8) ?
Cu1 N1 . 1.9386(10) ?
Cu1 O4 . 1.9906(9) ?
Cu1 N2 . 2.0540(10) ?
Cu1 O8 . 2.3506(9) ?
O1 C1 . 1.2915(13) ?
O2 C8 . 1.3715(13) ?
O2 C7 . 1.3805(13) ?
O3 C7 . 1.2179(14) ?
O4 H4C . 0.84(2) ?
O4 H4D . 0.82(2) ?
O5 N3 . 1.2505(13) ?
O6 N3 . 1.2497(13) ?
O7 N3 . 1.2531(13) ?
O8 H8C . 0.78(2) ?
O8 H8D . 0.78(2) ?
N1 C10 . 1.2872(14) ?
N1 C11 . 1.4636(15) ?
N2 C14 . 1.4790(16) ?
N2 C13 . 1.4801(17) ?
N2 C12 . 1.4828(15) ?
C1 C9 . 1.4265(15) ?
C1 C2 . 1.4277(15) ?
C2 C3 . 1.3660(15) ?
C2 H4 . 0.952(18) ?
C3 C4 . 1.4173(15) ?
C3 H2 . 0.920(18) ?
C4 C8 . 1.3876(15) ?
C4 C5 . 1.4395(15) ?
C5 C6 . 1.3603(16) ?
C5 C15 . 1.4932(16) ?
C6 C7 . 1.4275(16) ?
C6 H6 . 0.967(17) ?
C8 C9 . 1.4122(14) ?
C9 C10 . 1.4348(15) ?
C10 H10 . 0.925(17) ?
C11 C12 . 1.5180(17) ?
C11 H11A . 1.009(18) ?
C11 H11B . 0.918(19) ?
C12 H12A . 0.978(17) ?
C12 H12B . 0.953(17) ?
C13 H13A . 0.963(19) ?
C13 H13B . 0.952(19) ?
C13 H13C . 0.945(19) ?
C14 H14A . 0.97(2) ?
C14 H14B . 0.94(2) ?
C14 H14C . 0.951(17) ?
C15 H15A . 0.92(2) ?
C15 H15B . 0.971(19) ?
C15 H15C . 0.93(2) ?

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
O1 Cu1 N1 . . 92.33(4) ?
O1 Cu1 O4 . . 90.78(4) ?
N1 Cu1 O4 . . 170.33(4) ?
O1 Cu1 N2 . . 173.70(4) ?
N1 Cu1 N2 . . 85.00(4) ?
O4 Cu1 N2 . . 90.96(4) ?
O1 Cu1 O8 . . 94.56(4) ?
N1 Cu1 O8 . . 98.70(4) ?
O4 Cu1 O8 . . 90.17(4) ?
N2 Cu1 O8 . . 91.49(4) ?
C1 O1 Cu1 . . 127.22(7) ?
C8 O2 C7 . . 121.87(9) ?
Cu1 O4 H4C . . 106.2(14) ?
Cu1 O4 H4D . . 115.6(14) ?
H4C O4 H4D . . 110.(2) ?
Cu1 O8 H8C . . 113.3(15) ?
Cu1 O8 H8D . . 108.9(14) ?
H8C O8 H8D . . 110.0(19) ?
C10 N1 C11 . . 119.83(10) ?
C10 N1 Cu1 . . 126.44(8) ?
C11 N1 Cu1 . . 113.65(7) ?
C14 N2 C13 . . 108.54(11) ?
C14 N2 C12 . . 108.78(10) ?
C13 N2 C12 . . 110.35(10) ?
C14 N2 Cu1 . . 114.33(8) ?
C13 N2 Cu1 . . 110.08(8) ?
C12 N2 Cu1 . . 104.70(7) ?
O6 N3 O5 . . 120.48(10) ?
O6 N3 O7 . . 119.39(10) ?
O5 N3 O7 . . 120.12(10) ?
O1 C1 C9 . . 124.38(10) ?
O1 C1 C2 . . 118.19(10) ?
C9 C1 C2 . . 117.42(10) ?
C3 C2 C1 . . 122.27(10) ?
C3 C2 H4 . . 117.6(11) ?
C1 C2 H4 . . 120.1(11) ?
C2 C3 C4 . . 121.12(10) ?
C2 C3 H2 . . 119.6(11) ?
C4 C3 H2 . . 119.3(11) ?
C8 C4 C3 . . 117.11(10) ?
C8 C4 C5 . . 118.82(10) ?
C3 C4 C5 . . 124.07(10) ?
C6 C5 C4 . . 118.70(10) ?
C6 C5 C15 . . 120.41(10) ?
C4 C5 C15 . . 120.89(10) ?
C5 C6 C7 . . 122.30(10) ?
C5 C6 H6 . . 120.9(10) ?
C7 C6 H6 . . 116.8(10) ?
O3 C7 O2 . . 115.75(10) ?
O3 C7 C6 . . 126.93(10) ?
O2 C7 C6 . . 117.32(10) ?
O2 C8 C4 . . 120.99(10) ?
O2 C8 C9 . . 115.40(9) ?
C4 C8 C9 . . 123.61(10) ?
C8 C9 C1 . . 118.39(10) ?
C8 C9 C10 . . 118.69(10) ?
C1 C9 C10 . . 122.81(10) ?
N1 C10 C9 . . 124.62(10) ?
N1 C10 H10 . . 118.1(10) ?
C9 C10 H10 . . 117.3(10) ?
N1 C11 C12 . . 106.71(9) ?
N1 C11 H11A . . 108.8(10) ?
C12 C11 H11A . . 111.3(10) ?
N1 C11 H11B . . 111.0(12) ?
C12 C11 H11B . . 111.8(12) ?
H11A C11 H11B . . 107.3(15) ?
N2 C12 C11 . . 109.82(10) ?
N2 C12 H12A . . 107.5(10) ?
C11 C12 H12A . . 109.6(10) ?
N2 C12 H12B . . 108.5(10) ?
C11 C12 H12B . . 112.2(10) ?
H12A C12 H12B . . 109.1(14) ?
N2 C13 H13A . . 110.2(11) ?
N2 C13 H13B . . 106.6(11) ?
H13A C13 H13B . . 111.6(15) ?
N2 C13 H13C . . 109.7(11) ?
H13A C13 H13C . . 107.5(15) ?
H13B C13 H13C . . 111.2(16) ?
N2 C14 H14A . . 108.2(11) ?
N2 C14 H14B . . 110.8(12) ?
H14A C14 H14B . . 110.5(16) ?
N2 C14 H14C . . 109.4(10) ?
H14A C14 H14C . . 107.1(15) ?
H14B C14 H14C . . 110.6(16) ?
C5 C15 H15A . . 109.3(13) ?
C5 C15 H15B . . 111.5(11) ?
H15A C15 H15B . . 110.0(16) ?
C5 C15 H15C . . 110.1(14) ?
H15A C15 H15C . . 109.0(19) ?
H15B C15 H15C . . 106.8(18) ?



####################################################################### 
# 
# 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_SND29A_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2105919'
loop_
_audit_author_name
_audit_author_address
'Dr. Pabitra Baran Chatterjee'
;Central Salt and Marine Chemicals Research Institute, Bhavnagar
India
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N2 O3'
_chemical_formula_weight         274.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9174(3)
_cell_length_b                   8.2811(3)
_cell_length_c                   11.2569(5)
_cell_angle_alpha                73.4860(10)
_cell_angle_beta                 72.5660(10)
_cell_angle_gamma                83.895(2)
_cell_volume                     674.92(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6118
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      31.51

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   0.6973
_exptl_transmission_factor_max   0.7462
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.945
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'MICROFOCUS SEALED TUBE'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9015
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         31.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4351
_reflns_number_gt                3863
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4351
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.88192(7) 0.57594(7) 0.18457(5) 0.01466(12) Uani 1 1 d . . . . .
O2 O 1.03616(8) 0.76772(8) 0.01775(6) 0.02191(14) Uani 1 1 d . . . . .
O3 O 0.56603(8) 0.14113(8) 0.52756(6) 0.02027(13) Uani 1 1 d . . . . .
N1 N 0.63450(8) 0.13534(8) 0.28770(6) 0.01425(13) Uani 1 1 d . . . . .
N2 N 0.40998(9) 0.27874(9) 0.10581(7) 0.01856(14) Uani 1 1 d . . . . .
C1 C 0.97272(10) 0.72605(9) 0.13409(8) 0.01590(15) Uani 1 1 d . . . . .
C2 C 0.98188(10) 0.81508(10) 0.22408(8) 0.01716(15) Uani 1 1 d . . . . .
H2 H 1.040133 0.919787 0.192356 0.021 Uiso 1 1 calc R U . . .
C3 C 0.90975(10) 0.75414(10) 0.35329(8) 0.01585(15) Uani 1 1 d . . . . .
C4 C 0.82165(10) 0.59560(9) 0.40186(7) 0.01455(14) Uani 1 1 d . . . . .
C5 C 0.74183(10) 0.51941(10) 0.53535(8) 0.01736(15) Uani 1 1 d . . . . .
H5 H 0.747107 0.574995 0.597226 0.021 Uiso 1 1 calc R U . . .
C6 C 0.65845(11) 0.36991(10) 0.57702(7) 0.01810(15) Uani 1 1 d . . . . .
H6 H 0.607720 0.323679 0.667013 0.022 Uiso 1 1 calc R U . . .
C7 C 0.64512(10) 0.27997(10) 0.48823(7) 0.01538(14) Uani 1 1 d . . . . .
C8 C 0.72537(9) 0.35509(9) 0.35232(7) 0.01341(14) Uani 1 1 d . . . . .
C9 C 0.81070(9) 0.51102(9) 0.31439(7) 0.01304(14) Uani 1 1 d . . . . .
C10 C 0.91985(11) 0.85130(11) 0.44461(9) 0.02124(17) Uani 1 1 d . . . . .
H10A H 0.986843 0.953903 0.395981 0.032 Uiso 1 1 calc R U . . .
H10B H 0.979372 0.781806 0.507193 0.032 Uiso 1 1 calc R U . . .
H10C H 0.799934 0.881758 0.490397 0.032 Uiso 1 1 calc R U . . .
C11 C 0.71426(9) 0.27705(9) 0.25770(7) 0.01350(14) Uani 1 1 d . . . . .
H11 H 0.767070 0.330346 0.169153 0.016 Uiso 1 1 calc R U . . .
C12 C 0.60639(9) 0.05699(9) 0.19467(7) 0.01453(14) Uani 1 1 d . . . . .
H12A H 0.619226 -0.066942 0.225279 0.017 Uiso 1 1 calc R U . . .
H12B H 0.696376 0.095868 0.110484 0.017 Uiso 1 1 calc R U . . .
C13 C 0.42152(10) 0.10359(10) 0.17832(8) 0.01689(15) Uani 1 1 d . . . . .
H13A H 0.392043 0.029427 0.132524 0.020 Uiso 1 1 calc R U . . .
H13B H 0.333940 0.085088 0.264480 0.020 Uiso 1 1 calc R U . . .
C14 C 0.22798(12) 0.34413(13) 0.13599(10) 0.0284(2) Uani 1 1 d . . . . .
H14A H 0.224162 0.461919 0.086079 0.043 Uiso 1 1 calc R U . . .
H14B H 0.184572 0.337133 0.228453 0.043 Uiso 1 1 calc R U . . .
H14C H 0.152994 0.277237 0.113708 0.043 Uiso 1 1 calc R U . . .
C15 C 0.47878(13) 0.29737(11) -0.03290(8) 0.02451(18) Uani 1 1 d . . . . .
H15A H 0.477506 0.416952 -0.079278 0.037 Uiso 1 1 calc R U . . .
H15B H 0.404566 0.235557 -0.059989 0.037 Uiso 1 1 calc R U . . .
H15C H 0.600480 0.252114 -0.052577 0.037 Uiso 1 1 calc R U . . .
H1C H 0.5829(19) 0.0890(18) 0.3740(15) 0.041(4) 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
O1 C9 1.3662(9) . ?
O1 C1 1.3887(9) . ?
O2 C1 1.2133(10) . ?
O3 C7 1.2679(9) . ?
N1 C11 1.3018(9) . ?
N1 C12 1.4572(9) . ?
N1 H1C 0.917(15) . ?
N2 C13 1.4567(10) . ?
N2 C15 1.4594(11) . ?
N2 C14 1.4596(11) . ?
C1 C2 1.4335(11) . ?
C2 C3 1.3575(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.4378(10) . ?
C3 C10 1.4978(11) . ?
C4 C9 1.3870(10) . ?
C4 C5 1.4256(11) . ?
C5 C6 1.3590(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.4381(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.4463(10) . ?
C8 C9 1.4161(10) . ?
C8 C11 1.4211(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C12 C13 1.5251(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 122.02(6) . . ?
C11 N1 C12 124.79(6) . . ?
C11 N1 H1C 116.2(9) . . ?
C12 N1 H1C 118.7(9) . . ?
C13 N2 C15 110.98(6) . . ?
C13 N2 C14 111.23(7) . . ?
C15 N2 C14 109.76(7) . . ?
O2 C1 O1 116.09(7) . . ?
O2 C1 C2 126.92(7) . . ?
O1 C1 C2 116.99(7) . . ?
C3 C2 C1 121.93(7) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.27(7) . . ?
C2 C3 C10 120.59(7) . . ?
C4 C3 C10 120.14(7) . . ?
C9 C4 C5 117.25(7) . . ?
C9 C4 C3 118.65(7) . . ?
C5 C4 C3 124.10(7) . . ?
C6 C5 C4 122.18(7) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 121.61(7) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
O3 C7 C6 121.35(7) . . ?
O3 C7 C8 121.57(7) . . ?
C6 C7 C8 117.08(7) . . ?
C9 C8 C11 120.27(7) . . ?
C9 C8 C7 118.90(7) . . ?
C11 C8 C7 120.80(7) . . ?
O1 C9 C4 121.09(7) . . ?
O1 C9 C8 115.92(6) . . ?
C4 C9 C8 122.99(7) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C8 122.52(7) . . ?
N1 C11 H11 118.7 . . ?
C8 C11 H11 118.7 . . ?
N1 C12 C13 109.73(6) . . ?
N1 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 C12 111.43(6) . . ?
N2 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C9 O1 C1 O2 177.15(7) . . . . ?
C9 O1 C1 C2 -2.81(10) . . . . ?
O2 C1 C2 C3 -178.17(8) . . . . ?
O1 C1 C2 C3 1.79(11) . . . . ?
C1 C2 C3 C4 0.09(12) . . . . ?
C1 C2 C3 C10 -179.30(7) . . . . ?
C2 C3 C4 C9 -1.04(11) . . . . ?
C10 C3 C4 C9 178.35(7) . . . . ?
C2 C3 C4 C5 179.78(7) . . . . ?
C10 C3 C4 C5 -0.83(11) . . . . ?
C9 C4 C5 C6 0.22(12) . . . . ?
C3 C4 C5 C6 179.41(7) . . . . ?
C4 C5 C6 C7 -0.33(12) . . . . ?
C5 C6 C7 O3 -179.47(7) . . . . ?
C5 C6 C7 C8 0.36(11) . . . . ?
O3 C7 C8 C9 179.54(7) . . . . ?
C6 C7 C8 C9 -0.29(10) . . . . ?
O3 C7 C8 C11 1.55(11) . . . . ?
C6 C7 C8 C11 -178.28(6) . . . . ?
C1 O1 C9 C4 1.94(11) . . . . ?
C1 O1 C9 C8 -178.56(6) . . . . ?
C5 C4 C9 O1 179.30(6) . . . . ?
C3 C4 C9 O1 0.06(11) . . . . ?
C5 C4 C9 C8 -0.16(11) . . . . ?
C3 C4 C9 C8 -179.39(6) . . . . ?
C11 C8 C9 O1 -1.28(10) . . . . ?
C7 C8 C9 O1 -179.27(6) . . . . ?
C11 C8 C9 C4 178.21(6) . . . . ?
C7 C8 C9 C4 0.21(11) . . . . ?
C12 N1 C11 C8 174.65(6) . . . . ?
C9 C8 C11 N1 -178.76(6) . . . . ?
C7 C8 C11 N1 -0.80(11) . . . . ?
C11 N1 C12 C13 -96.31(8) . . . . ?
C15 N2 C13 C12 82.04(8) . . . . ?
C14 N2 C13 C12 -155.46(7) . . . . ?
N1 C12 C13 N2 72.67(8) . . . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SND78
_database_code_depnum_ccdc_archive 'CCDC 2105920'
loop_
_audit_author_name
_audit_author_address
'Dr. Pabitra Baran Chatterjee'
;Central Salt and Marine Chemicals Research Institute, Bhavnagar
India
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         260.29

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   24.1002(10)
_cell_length_b                   7.6010(3)
_cell_length_c                   6.9925(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.323(2)
_cell_angle_gamma                90
_cell_volume                     1275.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5241
_cell_measurement_theta_min      2.5463
_cell_measurement_theta_max      30.5598
_cell_measurement_temperature    117.(2)

_exptl_crystal_description       PLATES
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.012
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9990

_exptl_special_details           
;
;

_diffrn_ambient_temperature      117.(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            19598
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_full        30.56
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             3823
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_gt          0.1764
_refine_ls_wR_factor_ref         0.1960
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     214
_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)+(0.0687P)²+1.4490P] 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         0.640
_refine_diff_density_min         -0.288
_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 0.77948(7) 0.4633(2) 0.7771(3) 0.0390(4) Uani d . . . 1 . .
O O2 0.62753(5) 0.11362(18) 0.52240(19) 0.0200(3) Uani d . . . 1 . .
O O3 0.55897(6) -0.0613(2) 0.4081(2) 0.0286(4) Uani d . . . 1 . .
N N1 0.78378(8) 0.1228(3) 0.7870(3) 0.0293(4) Uani d . . . 1 . .
N N2 0.89695(9) 0.0426(3) 0.6698(4) 0.0449(6) Uani d . . . 1 . .
C C1 0.73024(9) 0.4511(3) 0.6938(3) 0.0290(5) Uani d . . . 1 . .
C C2 0.69811(12) 0.6033(3) 0.6350(4) 0.0375(6) Uani d . . . 1 . .
C C3 0.64584(11) 0.5920(3) 0.5472(3) 0.0314(5) Uani d . . . 1 . .
C C4 0.61993(9) 0.4272(3) 0.5061(3) 0.0226(4) Uani d . . . 1 . .
C C5 0.56469(9) 0.4059(3) 0.4154(3) 0.0251(4) Uani d . . . 1 . .
C C6 0.54235(8) 0.2467(3) 0.3818(3) 0.0250(4) Uani d . . . 1 . .
C C7 0.57349(8) 0.0891(3) 0.4334(3) 0.0221(4) Uani d . . . 1 . .
C C8 0.64976(8) 0.2772(3) 0.5593(3) 0.0193(4) Uani d . . . 1 . .
C C9 0.70439(8) 0.2825(3) 0.6520(3) 0.0218(4) Uani d . . . 1 . .
C C10 0.73342(9) 0.1265(3) 0.7020(3) 0.0246(4) Uani d . . . 1 . .
C C11 0.81475(10) -0.0378(3) 0.8361(4) 0.0380(6) Uani d . . . 1 . .
C C12 0.85296(11) -0.0839(3) 0.6860(4) 0.0389(6) Uani d . . . 1 . .
C C13 0.94127(13) 0.0209(5) 0.8213(6) 0.0660(10) Uani d . . . 1 . .
H H13A 0.956456 -0.098401 0.816362 0.099 Uiso calc U . R 1 . .
H H13B 0.926662 0.039894 0.945853 0.099 Uiso calc U . R 1 . .
H H13C 0.970812 0.106651 0.804545 0.099 Uiso calc U . R 1 . .
C C14 0.91958(15) 0.0239(5) 0.4821(6) 0.0660(10) Uani d . . . 1 . .
H H14A 0.89015 0.048208 0.379169 0.099 Uiso calc U . R 1 . .
H H14B 0.933377 -0.096308 0.468457 0.099 Uiso calc U . R 1 . .
H H14C 0.950255 0.10738 0.473867 0.099 Uiso calc U . R 1 . .
H H2 0.7138(13) 0.712(4) 0.661(4) 0.050(9) Uiso d . . . 1 . .
H H1C 0.7981(13) 0.225(4) 0.809(4) 0.047(9) Uiso d . . . 1 . .
H H3 0.6262(13) 0.690(4) 0.512(4) 0.048(8) Uiso d . . . 1 . .
H H5 0.5436(11) 0.504(4) 0.378(4) 0.029(6) Uiso d . . . 1 . .
H H6 0.5057(12) 0.230(4) 0.328(4) 0.039(7) Uiso d . . . 1 . .
H H10 0.7157(11) 0.014(4) 0.680(4) 0.031(7) Uiso d . . . 1 . .
H H11A 0.8373(12) -0.018(4) 0.966(4) 0.039(7) Uiso d . . . 1 . .
H H11B 0.7891(12) -0.134(4) 0.848(4) 0.039(7) Uiso d . . . 1 . .
H H12A 0.8307(14) -0.093(4) 0.560(5) 0.058(10) Uiso d . . . 1 . .
H H12B 0.8699(12) -0.200(4) 0.716(4) 0.041(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 C1 . 1.276(3) ?
O2 C8 . 1.369(2) ?
O2 C7 . 1.403(2) ?
O3 C7 . 1.204(3) ?
N1 C10 . 1.301(3) ?
N1 C11 . 1.455(3) ?
N1 H1C . 0.86(3) ?
N2 C13 . 1.442(4) ?
N2 C12 . 1.443(4) ?
N2 C14 . 1.474(4) ?
C1 C2 . 1.432(3) ?
C1 C9 . 1.443(3) ?
C2 C3 . 1.352(4) ?
C2 H2 . 0.92(3) ?
C3 C4 . 1.418(3) ?
C3 H3 . 0.91(3) ?
C4 C8 . 1.380(3) ?
C4 C5 . 1.430(3) ?
C5 C6 . 1.337(3) ?
C5 H5 . 0.93(3) ?
C6 C7 . 1.442(3) ?
C6 H6 . 0.94(3) ?
C8 C9 . 1.413(3) ?
C9 C10 . 1.404(3) ?
C10 H10 . 0.96(3) ?
C11 C12 . 1.501(4) ?
C11 H11A . 1.03(3) ?
C11 H11B . 0.97(3) ?
C12 H12A . 0.99(4) ?
C12 H12B . 0.98(3) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?

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 C7 . . 122.37(15) ?
C10 N1 C11 . . 124.2(2) ?
C10 N1 H1C . . 114.(2) ?
C11 N1 H1C . . 122.(2) ?
C13 N2 C12 . . 111.4(3) ?
C13 N2 C14 . . 109.4(3) ?
C12 N2 C14 . . 109.9(3) ?
O1 C1 C2 . . 121.9(2) ?
O1 C1 C9 . . 121.5(2) ?
C2 C1 C9 . . 116.59(19) ?
C3 C2 C1 . . 122.4(2) ?
C3 C2 H2 . . 120.(2) ?
C1 C2 H2 . . 118.(2) ?
C2 C3 C4 . . 121.5(2) ?
C2 C3 H3 . . 121.(2) ?
C4 C3 H3 . . 118.(2) ?
C8 C4 C3 . . 117.83(19) ?
C8 C4 C5 . . 117.81(19) ?
C3 C4 C5 . . 124.35(19) ?
C6 C5 C4 . . 121.55(19) ?
C6 C5 H5 . . 118.6(16) ?
C4 C5 H5 . . 119.9(16) ?
C5 C6 C7 . . 121.11(18) ?
C5 C6 H6 . . 122.8(18) ?
C7 C6 H6 . . 116.1(18) ?
O3 C7 O2 . . 115.92(18) ?
O3 C7 C6 . . 127.92(19) ?
O2 C7 C6 . . 116.16(17) ?
O2 C8 C4 . . 120.97(17) ?
O2 C8 C9 . . 116.37(16) ?
C4 C8 C9 . . 122.66(18) ?
C10 C9 C8 . . 120.75(18) ?
C10 C9 C1 . . 120.23(18) ?
C8 C9 C1 . . 119.02(18) ?
N1 C10 C9 . . 123.7(2) ?
N1 C10 H10 . . 115.8(16) ?
C9 C10 H10 . . 120.5(16) ?
N1 C11 C12 . . 111.4(2) ?
N1 C11 H11A . . 107.8(16) ?
C12 C11 H11A . . 110.1(16) ?
N1 C11 H11B . . 109.9(17) ?
C12 C11 H11B . . 108.8(17) ?
H11A C11 H11B . . 109.(2) ?
N2 C12 C11 . . 113.7(2) ?
N2 C12 H12A . . 109.(2) ?
C11 C12 H12A . . 109.(2) ?
N2 C12 H12B . . 108.6(17) ?
C11 C12 H12B . . 109.4(17) ?
H12A C12 H12B . . 108.(3) ?
N2 C13 H13A . . 109.5 ?
N2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 H14A . . 109.5 ?
N2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?



####################################################################### 
# 
# 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_SND79
_database_code_depnum_ccdc_archive 'CCDC 2105921'
loop_
_audit_author_name
_audit_author_address
'Dr. Pabitra Baran Chatterjee'
;Central Salt and Marine Chemicals Research Institute, Bhavnagar
India
;
_audit_update_record             
;
2021-08-27 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         288.34

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.661(2)
_cell_length_b                   24.120(5)
_cell_length_c                   10.644(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.846(13)
_cell_angle_gamma                90
_cell_volume                     2906.8(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9942
_cell_measurement_theta_min      2.4710
_cell_measurement_theta_max      28.3165
_cell_measurement_temperature    113.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.523
_exptl_crystal_size_mid          0.502
_exptl_crystal_size_min          0.490
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232

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


_exptl_absorpt_correction_T_min  0.9540
_exptl_absorpt_correction_T_max  0.9560

_exptl_special_details           
;
;

_diffrn_ambient_temperature      113.(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            43570
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             7164
_reflns_number_gt                6531
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1122
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         7164
_refine_ls_number_parameters     539
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0614P)²+0.9387P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.190
_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 0.88007(7) 0.48246(3) 0.26596(7) 0.02396(17) Uani d . . . 1 . .
H H1C 0.9141(14) 0.4479(7) 0.4346(15) 0.038(4) Uiso d . . . 1 . .
O O2 1.02728(6) 0.30221(3) 0.21639(6) 0.01755(15) Uani d . . . 1 . .
O O3 1.11060(7) 0.22011(3) 0.20738(8) 0.02428(17) Uani d . . . 1 . .
O O4 0.82806(7) 0.51641(3) 0.52454(7) 0.02188(16) Uani d . . . 1 . .
O O5 0.67535(6) 0.69549(3) 0.57033(7) 0.01908(15) Uani d . . . 1 . .
O O6 0.60362(8) 0.77981(3) 0.58078(8) 0.02837(18) Uani d . . . 1 . .
N N1 0.93396(7) 0.41248(3) 0.46103(8) 0.01654(16) Uani d . . . 1 . .
N N2 0.75963(8) 0.33497(4) 0.51146(9) 0.02172(18) Uani d . . . 1 . .
N N3 0.77176(7) 0.58538(3) 0.32922(8) 0.01700(16) Uani d . . . 1 . .
N N4 0.52610(8) 0.57495(4) 0.15483(9) 0.02270(19) Uani d . . . 1 . .
C C1 0.90756(9) 0.44513(4) 0.19496(9) 0.01854(19) Uani d . . . 1 . .
C C2 0.90188(10) 0.45509(4) 0.05964(10) 0.0222(2) Uani d . . . 1 . .
C C3 0.93833(9) 0.41657(4) -0.01520(10) 0.0220(2) Uani d . . . 1 . .
C C4 0.98202(9) 0.36365(4) 0.03401(9) 0.01853(19) Uani d . . . 1 . .
C C5 1.02782(9) 0.32316(4) -0.03855(9) 0.0212(2) Uani d . . . 1 . .
C C6 1.07331(9) 0.27478(4) 0.01555(10) 0.0218(2) Uani d . . . 1 . .
C C7 1.07432(9) 0.26208(4) 0.14818(10) 0.01896(19) Uani d . . . 1 . .
C C8 0.98454(8) 0.35211(4) 0.16289(9) 0.01599(18) Uani d . . . 1 . .
C C9 0.94784(8) 0.39065(4) 0.24526(9) 0.01635(18) Uani d . . . 1 . .
C C10 0.95478(8) 0.37709(4) 0.37701(9) 0.01604(18) Uani d . . . 1 . .
C C11 0.92893(9) 0.39715(4) 0.59194(9) 0.01747(18) Uani d . . . 1 . .
C C12 0.80149(9) 0.38266(4) 0.59442(10) 0.0204(2) Uani d . . . 1 . .
C C13 0.63898(11) 0.34056(5) 0.43277(13) 0.0324(3) Uani d . . . 1 . .
C C14 0.63115(13) 0.38165(6) 0.32316(15) 0.0416(3) Uani d . . . 1 . .
C C15 0.78467(11) 0.28159(5) 0.57818(12) 0.0304(2) Uani d . . . 1 . .
C C16 0.70676(18) 0.26559(6) 0.66796(17) 0.0512(4) Uani d . . . 1 . .
C C17 0.79334(8) 0.55243(4) 0.59329(9) 0.01719(18) Uani d . . . 1 . .
C C18 0.79362(9) 0.54172(4) 0.72701(10) 0.0201(2) Uani d . . . 1 . .
C C19 0.75563(9) 0.58030(4) 0.80078(10) 0.0202(2) Uani d . . . 1 . .
C C20 0.71360(9) 0.63348(4) 0.75160(9) 0.01819(19) Uani d . . . 1 . .
C C21 0.66998(9) 0.67491(4) 0.82396(10) 0.0208(2) Uani d . . . 1 . .
C C22 0.62992(9) 0.72418(4) 0.77028(10) 0.0216(2) Uani d . . . 1 . .
C C23 0.63323(9) 0.73707(4) 0.63909(10) 0.0205(2) Uani d . . . 1 . .
C C24 0.71333(8) 0.64509(4) 0.62376(9) 0.01610(18) Uani d . . . 1 . .
C C25 0.75096(8) 0.60648(4) 0.54189(9) 0.01610(18) Uani d . . . 1 . .
C C26 0.73900(8) 0.61918(4) 0.40907(9) 0.01646(18) Uani d . . . 1 . .
C C27 0.74105(9) 0.59232(4) 0.18918(9) 0.01862(19) Uani d . . . 1 . .
C C28 0.63680(9) 0.55386(4) 0.13191(10) 0.0220(2) Uani d . . . 1 . .
C C29 0.45539(10) 0.60276(5) 0.03881(11) 0.0267(2) Uani d . . . 1 . .
C C30 0.36613(12) 0.64301(6) 0.06867(16) 0.0398(3) Uani d . . . 1 . .
C C31 0.45807(11) 0.53197(5) 0.20296(11) 0.0292(2) Uani d . . . 1 . .
C C32 0.49897(12) 0.52411(6) 0.34770(12) 0.0342(3) Uani d . . . 1 . .
H H2 0.8710(13) 0.4916(7) 0.0249(15) 0.035(4) Uiso d . . . 1 . .
H H3 0.9383(13) 0.4252(6) -0.1044(15) 0.032(4) Uiso d . . . 1 . .
H H3C 0.8003(14) 0.5518(7) 0.3612(16) 0.040(4) Uiso d . . . 1 . .
H H5 1.0273(13) 0.3310(6) -0.1259(15) 0.032(4) Uiso d . . . 1 . .
H H6 1.1058(13) 0.2472(6) -0.0297(14) 0.031(4) Uiso d . . . 1 . .
H H10 0.9768(11) 0.3401(5) 0.4070(12) 0.018(3) Uiso d . . . 1 . .
H H11A 0.9572(11) 0.4286(5) 0.6507(12) 0.019(3) Uiso d . . . 1 . .
H H11B 0.9820(11) 0.3662(5) 0.6191(12) 0.020(3) Uiso d . . . 1 . .
H H12A 0.7523(12) 0.4146(5) 0.5649(13) 0.021(3) Uiso d . . . 1 . .
H H12B 0.7996(12) 0.3755(6) 0.6862(14) 0.027(3) Uiso d . . . 1 . .
H H13A 0.6124(14) 0.3031(7) 0.3988(15) 0.037(4) Uiso d . . . 1 . .
H H13B 0.5871(14) 0.3490(6) 0.4877(15) 0.036(4) Uiso d . . . 1 . .
H H14A 0.6838(19) 0.3673(9) 0.264(2) 0.068(6) Uiso d . . . 1 . .
H H14B 0.5470(16) 0.3855(7) 0.2729(17) 0.049(5) Uiso d . . . 1 . .
H H14C 0.6590(15) 0.4193(7) 0.3575(16) 0.043(4) Uiso d . . . 1 . .
H H15A 0.7732(14) 0.2482(7) 0.5121(15) 0.039(4) Uiso d . . . 1 . .
H H15B 0.8706(15) 0.2835(7) 0.6321(16) 0.041(4) Uiso d . . . 1 . .
H H16A 0.7045(18) 0.2959(9) 0.732(2) 0.066(6) Uiso d . . . 1 . .
H H16B 0.618(2) 0.2590(9) 0.616(2) 0.074(6) Uiso d . . . 1 . .
H H16C 0.7374(19) 0.2297(9) 0.718(2) 0.069(6) Uiso d . . . 1 . .
H H18 0.8249(12) 0.5051(6) 0.7630(13) 0.025(3) Uiso d . . . 1 . .
H H19 0.7582(13) 0.5723(6) 0.8899(15) 0.032(4) Uiso d . . . 1 . .
H H21 0.6691(13) 0.6677(6) 0.9133(15) 0.032(4) Uiso d . . . 1 . .
H H22 0.6023(13) 0.7530(6) 0.8173(14) 0.033(4) Uiso d . . . 1 . .
H H26 0.7033(12) 0.6531(6) 0.3750(13) 0.023(3) Uiso d . . . 1 . .
H H27A 0.7203(12) 0.6306(6) 0.1698(12) 0.021(3) Uiso d . . . 1 . .
H H27B 0.8102(11) 0.5812(5) 0.1581(12) 0.019(3) Uiso d . . . 1 . .
H H28A 0.6564(13) 0.5174(6) 0.1750(14) 0.031(4) Uiso d . . . 1 . .
H H28B 0.6326(12) 0.5497(6) 0.0376(14) 0.030(4) Uiso d . . . 1 . .
H H29A 0.5119(13) 0.6234(6) -0.0024(15) 0.033(4) Uiso d . . . 1 . .
H H29B 0.4121(13) 0.5743(6) -0.0277(14) 0.030(4) Uiso d . . . 1 . .
H H30A 0.4085(17) 0.6729(8) 0.1266(18) 0.054(5) Uiso d . . . 1 . .
H H30B 0.3111(17) 0.6230(8) 0.1150(18) 0.056(5) Uiso d . . . 1 . .
H H30C 0.3166(19) 0.6611(8) -0.016(2) 0.066(6) Uiso d . . . 1 . .
H H31A 0.4643(13) 0.4947(6) 0.1586(15) 0.034(4) Uiso d . . . 1 . .
H H31B 0.3741(15) 0.5437(7) 0.1829(15) 0.039(4) Uiso d . . . 1 . .
H H32A 0.4866(15) 0.5591(7) 0.3939(16) 0.044(4) Uiso d . . . 1 . .
H H32B 0.4509(16) 0.4945(8) 0.3777(17) 0.051(5) Uiso d . . . 1 . .
H H32C 0.5846(15) 0.5138(6) 0.3730(15) 0.036(4) 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 C1 . 1.2652(12) ?
O2 C8 . 1.3733(11) ?
O2 C7 . 1.3984(11) ?
O3 C7 . 1.2138(13) ?
O4 C17 . 1.2633(12) ?
O5 C24 . 1.3698(11) ?
O5 C23 . 1.3983(12) ?
O6 C23 . 1.2101(13) ?
N1 C10 . 1.3006(12) ?
N1 C11 . 1.4563(12) ?
N1 H1C . 0.911(16) ?
N2 C12 . 1.4611(13) ?
N2 C13 . 1.4612(15) ?
N2 C15 . 1.4656(14) ?
N3 C26 . 1.2993(13) ?
N3 C27 . 1.4569(12) ?
N3 H3C . 0.911(17) ?
N4 C28 . 1.4613(14) ?
N4 C31 . 1.4701(14) ?
N4 C29 . 1.4723(14) ?
C1 C2 . 1.4460(14) ?
C1 C9 . 1.4537(13) ?
C2 C3 . 1.3566(15) ?
C2 H2 . 0.989(16) ?
C3 C4 . 1.4268(14) ?
C3 H3 . 0.972(15) ?
C4 C8 . 1.3931(13) ?
C4 C5 . 1.4258(14) ?
C5 C6 . 1.3521(15) ?
C5 H5 . 0.947(15) ?
C6 C7 . 1.4418(14) ?
C6 H6 . 0.951(15) ?
C8 C9 . 1.4126(13) ?
C9 C10 . 1.4232(13) ?
C10 H10 . 0.962(13) ?
C11 C12 . 1.5330(14) ?
C11 H11A . 0.988(13) ?
C11 H11B . 0.968(13) ?
C12 H12A . 0.966(13) ?
C12 H12B . 0.998(14) ?
C13 C14 . 1.517(2) ?
C13 H13A . 0.994(16) ?
C13 H13B . 0.958(16) ?
C14 H14A . 1.04(2) ?
C14 H14B . 1.003(18) ?
C14 H14C . 1.003(17) ?
C15 C16 . 1.5177(19) ?
C15 H15A . 1.057(16) ?
C15 H15B . 1.030(17) ?
C16 H16A . 1.01(2) ?
C16 H16B . 1.07(2) ?
C16 H16C . 1.04(2) ?
C17 C18 . 1.4458(14) ?
C17 C25 . 1.4539(13) ?
C18 C19 . 1.3583(15) ?
C18 H18 . 0.996(14) ?
C19 C20 . 1.4271(14) ?
C19 H19 . 0.962(15) ?
C20 C24 . 1.3885(13) ?
C20 C21 . 1.4276(14) ?
C21 C22 . 1.3524(15) ?
C21 H21 . 0.969(15) ?
C22 C23 . 1.4400(14) ?
C22 H22 . 0.957(15) ?
C24 C25 . 1.4150(13) ?
C25 C26 . 1.4203(13) ?
C26 H26 . 0.950(14) ?
C27 C28 . 1.5347(14) ?
C27 H27A . 0.965(13) ?
C27 H27B . 0.979(13) ?
C28 H28A . 0.992(15) ?
C28 H28B . 0.998(14) ?
C29 C30 . 1.5117(17) ?
C29 H29A . 1.006(15) ?
C29 H29B . 1.028(15) ?
C30 H30A . 0.999(19) ?
C30 H30B . 1.019(19) ?
C30 H30C . 1.04(2) ?
C31 C32 . 1.5117(16) ?
C31 H31A . 1.026(15) ?
C31 H31B . 0.992(16) ?
C32 H32A . 1.005(17) ?
C32 H32B . 1.005(18) ?
C32 H32C . 1.001(16) ?

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 C7 . . 122.69(8) ?
C24 O5 C23 . . 122.57(8) ?
C10 N1 C11 . . 123.23(8) ?
C10 N1 H1C . . 118.6(10) ?
C11 N1 H1C . . 117.9(10) ?
C12 N2 C13 . . 114.23(9) ?
C12 N2 C15 . . 113.56(9) ?
C13 N2 C15 . . 114.31(9) ?
C26 N3 C27 . . 123.95(8) ?
C26 N3 H3C . . 116.9(10) ?
C27 N3 H3C . . 117.6(10) ?
C28 N4 C31 . . 112.62(9) ?
C28 N4 C29 . . 111.00(8) ?
C31 N4 C29 . . 111.90(9) ?
O1 C1 C2 . . 121.26(9) ?
O1 C1 C9 . . 121.93(9) ?
C2 C1 C9 . . 116.80(9) ?
C3 C2 C1 . . 121.66(9) ?
C3 C2 H2 . . 121.9(9) ?
C1 C2 H2 . . 116.5(9) ?
C2 C3 C4 . . 122.12(9) ?
C2 C3 H3 . . 119.9(9) ?
C4 C3 H3 . . 117.9(9) ?
C8 C4 C5 . . 118.31(9) ?
C8 C4 C3 . . 117.50(9) ?
C5 C4 C3 . . 124.14(9) ?
C6 C5 C4 . . 121.34(9) ?
C6 C5 H5 . . 120.0(9) ?
C4 C5 H5 . . 118.6(9) ?
C5 C6 C7 . . 120.72(9) ?
C5 C6 H6 . . 123.5(9) ?
C7 C6 H6 . . 115.8(9) ?
O3 C7 O2 . . 116.04(9) ?
O3 C7 C6 . . 127.28(9) ?
O2 C7 C6 . . 116.67(8) ?
O2 C8 C4 . . 120.22(8) ?
O2 C8 C9 . . 116.96(8) ?
C4 C8 C9 . . 122.79(9) ?
C8 C9 C10 . . 120.39(9) ?
C8 C9 C1 . . 119.03(8) ?
C10 C9 C1 . . 120.53(8) ?
N1 C10 C9 . . 123.40(9) ?
N1 C10 H10 . . 117.4(8) ?
C9 C10 H10 . . 119.2(8) ?
N1 C11 C12 . . 109.61(8) ?
N1 C11 H11A . . 109.1(7) ?
C12 C11 H11A . . 110.0(7) ?
N1 C11 H11B . . 108.2(8) ?
C12 C11 H11B . . 111.9(8) ?
H11A C11 H11B . . 108.1(11) ?
N2 C12 C11 . . 110.74(8) ?
N2 C12 H12A . . 110.1(8) ?
C11 C12 H12A . . 108.4(8) ?
N2 C12 H12B . . 112.0(8) ?
C11 C12 H12B . . 107.8(8) ?
H12A C12 H12B . . 107.7(11) ?
N2 C13 C14 . . 111.94(10) ?
N2 C13 H13A . . 107.4(9) ?
C14 C13 H13A . . 111.0(9) ?
N2 C13 H13B . . 109.3(9) ?
C14 C13 H13B . . 113.6(9) ?
H13A C13 H13B . . 103.1(13) ?
C13 C14 H14A . . 108.2(12) ?
C13 C14 H14B . . 110.0(10) ?
H14A C14 H14B . . 110.7(15) ?
C13 C14 H14C . . 110.9(10) ?
H14A C14 H14C . . 109.7(15) ?
H14B C14 H14C . . 107.4(14) ?
N2 C15 C16 . . 116.66(11) ?
N2 C15 H15A . . 111.6(9) ?
C16 C15 H15A . . 103.0(9) ?
N2 C15 H15B . . 106.5(9) ?
C16 C15 H15B . . 108.0(9) ?
H15A C15 H15B . . 110.9(12) ?
C15 C16 H16A . . 111.2(12) ?
C15 C16 H16B . . 111.7(12) ?
H16A C16 H16B . . 106.2(16) ?
C15 C16 H16C . . 110.8(12) ?
H16A C16 H16C . . 108.3(16) ?
H16B C16 H16C . . 108.5(16) ?
O4 C17 C18 . . 121.46(9) ?
O4 C17 C25 . . 121.73(9) ?
C18 C17 C25 . . 116.81(9) ?
C19 C18 C17 . . 121.50(9) ?
C19 C18 H18 . . 121.7(8) ?
C17 C18 H18 . . 116.8(8) ?
C18 C19 C20 . . 122.31(9) ?
C18 C19 H19 . . 119.6(9) ?
C20 C19 H19 . . 118.0(9) ?
C24 C20 C19 . . 117.44(9) ?
C24 C20 C21 . . 118.03(9) ?
C19 C20 C21 . . 124.52(9) ?
C22 C21 C20 . . 121.25(9) ?
C22 C21 H21 . . 119.3(9) ?
C20 C21 H21 . . 119.5(9) ?
C21 C22 C23 . . 120.85(9) ?
C21 C22 H22 . . 122.9(9) ?
C23 C22 H22 . . 116.1(9) ?
O6 C23 O5 . . 115.81(9) ?
O6 C23 C22 . . 127.65(9) ?
O5 C23 C22 . . 116.54(9) ?
O5 C24 C20 . . 120.70(8) ?
O5 C24 C25 . . 116.45(8) ?
C20 C24 C25 . . 122.85(9) ?
C24 C25 C26 . . 120.00(8) ?
C24 C25 C17 . . 119.08(8) ?
C26 C25 C17 . . 120.76(8) ?
N3 C26 C25 . . 122.79(9) ?
N3 C26 H26 . . 117.5(8) ?
C25 C26 H26 . . 119.7(8) ?
N3 C27 C28 . . 108.32(8) ?
N3 C27 H27A . . 108.4(8) ?
C28 C27 H27A . . 111.1(8) ?
N3 C27 H27B . . 107.1(8) ?
C28 C27 H27B . . 109.8(7) ?
H27A C27 H27B . . 112.0(11) ?
N4 C28 C27 . . 111.75(8) ?
N4 C28 H28A . . 110.3(9) ?
C27 C28 H28A . . 106.2(8) ?
N4 C28 H28B . . 111.7(8) ?
C27 C28 H28B . . 107.7(8) ?
H28A C28 H28B . . 109.0(12) ?
N4 C29 C30 . . 113.07(11) ?
N4 C29 H29A . . 107.3(9) ?
C30 C29 H29A . . 109.3(9) ?
N4 C29 H29B . . 111.0(8) ?
C30 C29 H29B . . 108.9(8) ?
H29A C29 H29B . . 107.2(12) ?
C29 C30 H30A . . 109.2(11) ?
C29 C30 H30B . . 110.1(11) ?
H30A C30 H30B . . 108.5(15) ?
C29 C30 H30C . . 110.7(11) ?
H30A C30 H30C . . 108.7(15) ?
H30B C30 H30C . . 109.5(16) ?
N4 C31 C32 . . 112.25(9) ?
N4 C31 H31A . . 110.8(9) ?
C32 C31 H31A . . 108.6(8) ?
N4 C31 H31B . . 108.2(9) ?
C32 C31 H31B . . 108.0(9) ?
H31A C31 H31B . . 109.0(12) ?
C31 C32 H32A . . 110.2(10) ?
C31 C32 H32B . . 110.4(10) ?
H32A C32 H32B . . 106.5(14) ?
C31 C32 H32C . . 110.8(9) ?
H32A C32 H32C . . 109.2(13) ?
H32B C32 H32C . . 109.5(14) ?

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
O1 C1 C2 C3 . . . . 175.71(10) ?
C9 C1 C2 C3 . . . . -3.44(15) ?
C1 C2 C3 C4 . . . . 1.34(17) ?
C2 C3 C4 C8 . . . . 0.97(15) ?
C2 C3 C4 C5 . . . . -176.10(10) ?
C8 C4 C5 C6 . . . . -0.34(15) ?
C3 C4 C5 C6 . . . . 176.71(10) ?
C4 C5 C6 C7 . . . . 1.48(16) ?
C8 O2 C7 O3 . . . . 178.97(8) ?
C8 O2 C7 C6 . . . . -1.64(13) ?
C5 C6 C7 O3 . . . . 178.79(10) ?
C5 C6 C7 O2 . . . . -0.52(14) ?
C7 O2 C8 C4 . . . . 2.82(13) ?
C7 O2 C8 C9 . . . . -175.27(8) ?
C5 C4 C8 O2 . . . . -1.78(14) ?
C3 C4 C8 O2 . . . . -179.03(8) ?
C5 C4 C8 C9 . . . . 176.20(9) ?
C3 C4 C8 C9 . . . . -1.05(14) ?
O2 C8 C9 C10 . . . . -0.56(13) ?
C4 C8 C9 C10 . . . . -178.60(9) ?
O2 C8 C9 C1 . . . . 176.90(8) ?
C4 C8 C9 C1 . . . . -1.14(14) ?
O1 C1 C9 C8 . . . . -175.86(9) ?
C2 C1 C9 C8 . . . . 3.28(14) ?
O1 C1 C9 C10 . . . . 1.60(15) ?
C2 C1 C9 C10 . . . . -179.26(9) ?
C11 N1 C10 C9 . . . . 173.31(9) ?
C8 C9 C10 N1 . . . . 172.75(9) ?
C1 C9 C10 N1 . . . . -4.68(15) ?
C10 N1 C11 C12 . . . . -91.42(11) ?
C13 N2 C12 C11 . . . . -137.44(10) ?
C15 N2 C12 C11 . . . . 89.04(10) ?
N1 C11 C12 N2 . . . . 62.03(10) ?
C12 N2 C13 C14 . . . . 72.61(13) ?
C15 N2 C13 C14 . . . . -154.22(11) ?
C12 N2 C15 C16 . . . . 76.16(14) ?
C13 N2 C15 C16 . . . . -57.32(15) ?
O4 C17 C18 C19 . . . . -179.59(9) ?
C25 C17 C18 C19 . . . . 0.25(14) ?
C17 C18 C19 C20 . . . . -0.15(16) ?
C18 C19 C20 C24 . . . . -0.42(15) ?
C18 C19 C20 C21 . . . . 178.34(10) ?
C24 C20 C21 C22 . . . . -0.27(15) ?
C19 C20 C21 C22 . . . . -179.03(10) ?
C20 C21 C22 C23 . . . . -1.84(16) ?
C24 O5 C23 O6 . . . . 179.27(9) ?
C24 O5 C23 C22 . . . . -0.82(14) ?
C21 C22 C23 O6 . . . . -177.74(11) ?
C21 C22 C23 O5 . . . . 2.35(15) ?
C23 O5 C24 C20 . . . . -1.26(14) ?
C23 O5 C24 C25 . . . . 178.51(8) ?
C19 C20 C24 O5 . . . . -179.33(8) ?
C21 C20 C24 O5 . . . . 1.82(14) ?
C19 C20 C24 C25 . . . . 0.90(14) ?
C21 C20 C24 C25 . . . . -177.94(9) ?
O5 C24 C25 C26 . . . . -5.16(13) ?
C20 C24 C25 C26 . . . . 174.61(9) ?
O5 C24 C25 C17 . . . . 179.42(8) ?
C20 C24 C25 C17 . . . . -0.81(14) ?
O4 C17 C25 C24 . . . . -179.95(9) ?
C18 C17 C25 C24 . . . . 0.21(13) ?
O4 C17 C25 C26 . . . . 4.67(14) ?
C18 C17 C25 C26 . . . . -175.17(9) ?
C27 N3 C26 C25 . . . . 168.02(9) ?
C24 C25 C26 N3 . . . . -179.89(9) ?
C17 C25 C26 N3 . . . . -4.55(14) ?
C26 N3 C27 C28 . . . . -99.84(11) ?
C31 N4 C28 C27 . . . . -133.26(9) ?
C29 N4 C28 C27 . . . . 100.39(10) ?
N3 C27 C28 N4 . . . . 74.43(10) ?
C28 N4 C29 C30 . . . . -158.37(10) ?
C31 N4 C29 C30 . . . . 74.88(12) ?
C28 N4 C31 C32 . . . . 83.61(13) ?
C29 N4 C31 C32 . . . . -150.52(11) ?



