# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1941859'
loop_
_audit_author_name
_audit_author_address
'Rohit Kumar Varshnaya'
;Indian Institute of Technology, Ropar
India
;
_audit_update_record             
;
2019-07-20 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N O4'
_chemical_formula_sum            'C19 H17 N O4'
_chemical_formula_weight         323.33

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.752(5)
_cell_length_b                   15.203(5)
_cell_length_c                   12.876(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 105.763(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1648.8(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    16629
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      29.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.30
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6519
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean 10.233
_diffrn_reflns_number            16629
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.861
_diffrn_reflns_theta_max         29.128
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4357
_reflns_number_gt                3048
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'APEX2 (Bruker, 2014); SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014);XPREP(Sheldrick,2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP, Platon, Mercury'
_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)+(0.0236P)²+0.7252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4357
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1223
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
O3 O 0.69493(14) 0.43155(8) 0.71360(9) 0.0423(3) Uani 1 1 d . . . . .
O1 O 0.60837(15) 0.37871(9) 0.36656(9) 0.0508(3) Uani 1 1 d . . . . .
O4 O 1.03545(16) 0.33078(9) 0.70596(11) 0.0600(4) Uani 1 1 d . . . . .
N1 N 0.72531(17) 0.48011(10) 0.62342(11) 0.0421(3) Uani 1 1 d . . . . .
O2 O 0.74052(19) 0.50589(10) 0.40264(10) 0.0643(4) Uani 1 1 d . . . . .
C7 C 0.74514(19) 0.40690(11) 0.54702(12) 0.0385(4) Uani 1 1 d . . . . .
C6 C 0.5981(2) 0.29569(11) 0.76016(13) 0.0415(4) Uani 1 1 d . . . . .
C5 C 0.7302(2) 0.24829(14) 0.81612(15) 0.0478(4) Uani 1 1 d . . . . .
H5 H 0.8223 0.2499 0.7933 0.056(6) Uani 1 1 calc R . . . .
C10 C 0.6019(2) 0.35503(12) 0.66723(14) 0.0406(4) Uani 1 1 d . . . . .
H10 H 0.4934 0.3737 0.6308 0.045(5) Uani 1 1 calc R . . . .
C11 C 0.8858(2) 0.45158(12) 0.61801(13) 0.0411(4) Uani 1 1 d . . . . .
H11 H 0.9377 0.4930 0.5801 0.048(5) Uani 1 1 calc R . . . .
C9 C 0.6821(2) 0.32263(12) 0.58295(15) 0.0417(4) Uani 1 1 d . . . . .
H9A H 0.7676 0.2820 0.6143 0.057(6) Uani 1 1 calc R . . . .
H9B H 0.6065 0.2941 0.5232 0.051(5) Uani 1 1 calc R . . . .
C8 C 0.6980(2) 0.43712(12) 0.43152(13) 0.0428(4) Uani 1 1 d . . . . .
C19 C 0.5588(3) 0.40134(19) 0.25251(17) 0.0649(6) Uani 1 1 d . . . . .
H19A H 0.4947 0.3548 0.2129 0.18(2) Uani 1 1 calc R . . . .
H19B H 0.4982 0.4548 0.2429 0.154(18) Uani 1 1 calc R . . . .
H19C H 0.6508 0.4094 0.2265 0.136(15) Uani 1 1 calc R . . . .
C13 C 1.0660(2) 0.46054(14) 0.81084(13) 0.0477(4) Uani 1 1 d . . . . .
C12 C 0.9977(2) 0.40712(13) 0.71316(13) 0.0429(4) Uani 1 1 d . . . . .
C1 C 0.4628(3) 0.29162(16) 0.7953(2) 0.0632(6) Uani 1 1 d . . . . .
H1 H 0.3721 0.3220 0.7582 0.075(7) Uani 1 1 calc R . . . .
C18 C 1.0377(3) 0.54899(16) 0.81622(17) 0.0656(6) Uani 1 1 d . . . . .
H18 H 0.9695 0.5773 0.7577 0.094(9) Uani 1 1 calc R . . . .
C2 C 0.4617(3) 0.24228(18) 0.8860(2) 0.0813(8) Uani 1 1 d . . . . .
H2 H 0.3702 0.2400 0.9094 0.108(10) Uani 1 1 calc R . . . .
C14 C 1.1653(4) 0.4201(2) 0.8987(2) 0.0866(9) Uani 1 1 d . . . . .
H14 H 1.1854 0.3602 0.8969 0.104(11) Uani 1 1 calc R . . . .
C3 C 0.7269(3) 0.19880(15) 0.90528(17) 0.0580(5) Uani 1 1 d . . . . .
H3 H 0.8158 0.1665 0.9412 0.086(8) Uani 1 1 calc R . . . .
C4 C 0.5942(3) 0.19695(16) 0.9410(2) 0.0689(7) Uani 1 1 d . . . . .
H4 H 0.5935 0.1651 1.0025 0.093(9) Uani 1 1 calc R . . . .
C16 C 1.2078(4) 0.5565(3) 0.9940(2) 0.1014(11) Uani 1 1 d . . . . .
H16 H 1.2560 0.5888 1.0555 0.137(13) Uani 1 1 calc R . . . .
C17 C 1.1099(4) 0.5962(2) 0.9079(2) 0.0883(9) Uani 1 1 d . . . . .
H17 H 1.0906 0.6562 0.9103 0.162(17) Uani 1 1 calc R . . . .
C15 C 1.2357(5) 0.4688(3) 0.9903(2) 0.1196(14) Uani 1 1 d . . . . .
H15 H 1.3028 0.4411 1.0498 0.161(16) Uani 1 1 calc R . . . .


_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
O3 C10 1.452(2) . ?
O3 N1 1.4601(18) . ?
O1 C8 1.322(2) . ?
O1 C19 1.455(2) . ?
O4 C12 1.217(2) . ?
N1 C11 1.490(2) . ?
N1 C7 1.526(2) . ?
O2 C8 1.202(2) . ?
C7 C11 1.484(2) . ?
C7 C8 1.503(2) . ?
C7 C9 1.516(2) . ?
C6 C1 1.379(3) . ?
C6 C5 1.387(3) . ?
C6 C10 1.506(2) . ?
C5 C3 1.380(3) . ?
C10 C9 1.526(2) . ?
C11 C12 1.505(2) . ?
C13 C14 1.370(3) . ?
C13 C18 1.372(3) . ?
C13 C12 1.480(3) . ?
C1 C2 1.390(3) . ?
C18 C17 1.379(3) . ?
C2 C4 1.369(4) . ?
C14 C15 1.387(4) . ?
C3 C4 1.361(3) . ?
C16 C17 1.345(4) . ?
C16 C15 1.359(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 N1 106.32(11) . . ?
C8 O1 C19 116.29(17) . . ?
O3 N1 C11 105.52(12) . . ?
O3 N1 C7 102.77(12) . . ?
C11 N1 C7 58.92(10) . . ?
C11 C7 C8 115.36(15) . . ?
C11 C7 C9 120.58(15) . . ?
C8 C7 C9 122.37(15) . . ?
C11 C7 N1 59.31(11) . . ?
C8 C7 N1 111.47(14) . . ?
C9 C7 N1 107.77(13) . . ?
C1 C6 C5 118.39(18) . . ?
C1 C6 C10 119.54(17) . . ?
C5 C6 C10 121.96(16) . . ?
C3 C5 C6 120.84(19) . . ?
O3 C10 C6 106.49(13) . . ?
O3 C10 C9 103.64(14) . . ?
C6 C10 C9 119.03(15) . . ?
C7 C11 N1 61.77(11) . . ?
C7 C11 C12 122.92(16) . . ?
N1 C11 C12 120.40(14) . . ?
C7 C9 C10 102.72(14) . . ?
O2 C8 O1 124.68(16) . . ?
O2 C8 C7 123.16(16) . . ?
O1 C8 C7 112.14(15) . . ?
C14 C13 C18 118.7(2) . . ?
C14 C13 C12 118.3(2) . . ?
C18 C13 C12 122.94(17) . . ?
O4 C12 C13 122.17(16) . . ?
O4 C12 C11 119.76(16) . . ?
C13 C12 C11 117.95(16) . . ?
C6 C1 C2 120.2(2) . . ?
C13 C18 C17 120.4(2) . . ?
C4 C2 C1 120.5(2) . . ?
C13 C14 C15 119.9(3) . . ?
C4 C3 C5 120.4(2) . . ?
C3 C4 C2 119.7(2) . . ?
C17 C16 C15 119.4(3) . . ?
C16 C17 C18 120.8(3) . . ?
C16 C15 C14 120.7(3) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2003588'
loop_
_audit_author_name
_audit_author_address
'Sandeep Singh Dhankhar'
;IIT Ropar
India
;
_audit_update_record             
;
2020-05-12 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N O4'
_chemical_formula_sum            'C11 H11 N O4'
_chemical_formula_weight         221.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.2819(7)
_cell_length_b                   8.8634(5)
_cell_length_c                   10.5907(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.721(2)
_cell_angle_gamma                90
_cell_volume                     1056.80(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    27564
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      28.4

_exptl_crystal_description       rectangular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   Sadabs

_exptl_absorpt_special_details   
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker D8 Venture PHOTON 100 CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27564
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.925
_diffrn_reflns_theta_max         28.352
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2626
_reflns_number_gt                2150
_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       'APEX2 (Bruker, 2014.3)'
_computing_cell_refinement       'APEX2 (Bruker, 2014.3);SAINT (Bruker, 2014)'
_computing_data_reduction        'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond, Platon'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0573P)²+0.2018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2626
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.10594(8) 0.23062(11) 0.56303(10) 0.0558(3) Uani 1 1 d . . . . .
O4 O 0.81687(8) 0.34030(11) 0.26261(8) 0.0520(3) Uani 1 1 d . . . . .
O2 O 1.15642(10) 0.42951(13) 0.44656(11) 0.0682(3) Uani 1 1 d . . . . .
O3 O 0.97273(10) 0.49582(12) 0.25655(11) 0.0665(3) Uani 1 1 d . . . . .
N1 N 0.93379(9) 0.38384(12) 0.30858(10) 0.0458(3) Uani 1 1 d . . . . .
C6 C 0.66754(10) 0.18061(14) 0.34466(11) 0.0419(3) Uani 1 1 d . . . . .
C3 C 0.97449(11) 0.29776(13) 0.40155(11) 0.0414(3) Uani 1 1 d . . . . .
C4 C 0.88590(11) 0.18180(15) 0.43213(12) 0.0447(3) Uani 1 1 d . . . . .
C5 C 0.79636(11) 0.19109(15) 0.31763(12) 0.0441(3) Uani 1 1 d . . . . .
C2 C 1.08875(11) 0.32989(15) 0.46923(12) 0.0458(3) Uani 1 1 d . . . . .
C11 C 0.59480(13) 0.07718(17) 0.27986(13) 0.0523(3) Uani 1 1 d . . . . .
C7 C 0.62017(13) 0.27262(18) 0.43490(14) 0.0552(3) Uani 1 1 d . . . . .
C10 C 0.47601(14) 0.0642(2) 0.30573(16) 0.0650(4) Uani 1 1 d . . . . .
C8 C 0.50118(14) 0.2602(2) 0.45875(16) 0.0680(4) Uani 1 1 d . . . . .
C1 C 1.21020(14) 0.2531(2) 0.64797(18) 0.0643(4) Uani 1 1 d . . . . .
C9 C 0.42992(14) 0.1555(2) 0.39426(16) 0.0680(4) Uani 1 1 d . . . . .
H1C H 1.276(2) 0.219(3) 0.610(2) 0.097(7) Uiso 1 1 d . . . . .
H1A H 1.197(2) 0.181(3) 0.724(2) 0.115(8) Uiso 1 1 d . . . . .
H1B H 1.219(2) 0.354(3) 0.671(2) 0.114(8) Uiso 1 1 d . . . . .
H4A H 0.9217(14) 0.0810(19) 0.4402(15) 0.059(4) Uiso 1 1 d . . . . .
H4B H 0.8502(13) 0.2088(17) 0.5086(15) 0.049(4) Uiso 1 1 d . . . . .
H11 H 0.6261(15) 0.0171(19) 0.2174(17) 0.063(5) Uiso 1 1 d . . . . .
H7 H 0.6704(14) 0.3450(19) 0.4819(16) 0.061(4) Uiso 1 1 d . . . . .
H9 H 0.3467(16) 0.144(2) 0.4156(17) 0.075(5) Uiso 1 1 d . . . . .
H10 H 0.428(2) -0.005(2) 0.259(2) 0.088(6) Uiso 1 1 d . . . . .
H8 H 0.4683(18) 0.326(2) 0.517(2) 0.091(6) Uiso 1 1 d . . . . .
H5 H 0.8142(12) 0.1183(17) 0.2541(13) 0.044(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 C2 1.3318(16) . ?
O1 C1 1.4475(18) . ?
O4 N1 1.4292(14) . ?
O4 C5 1.4696(16) . ?
O2 C2 1.2016(16) . ?
O3 N1 1.2301(14) . ?
N1 C3 1.3052(16) . ?
C6 C11 1.3826(18) . ?
C6 C7 1.3894(19) . ?
C6 C5 1.5022(17) . ?
C3 C2 1.4617(18) . ?
C3 C4 1.4839(17) . ?
C4 C5 1.5293(18) . ?
C4 H4A 0.981(17) . ?
C4 H4B 0.958(16) . ?
C5 H5 0.963(14) . ?
C11 C10 1.390(2) . ?
C11 H11 0.936(17) . ?
C7 C8 1.386(2) . ?
C7 H7 0.972(17) . ?
C10 C9 1.367(3) . ?
C10 H10 0.94(2) . ?
C8 C9 1.380(3) . ?
C8 H8 0.94(2) . ?
C1 H1C 0.91(2) . ?
C1 H1A 1.05(3) . ?
C1 H1B 0.93(3) . ?
C9 H9 0.985(18) . ?

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
C2 O1 C1 116.47(12) . . ?
N1 O4 C5 105.88(8) . . ?
O3 N1 C3 133.73(12) . . ?
O3 N1 O4 114.45(10) . . ?
C3 N1 O4 111.76(10) . . ?
C11 C6 C7 119.22(13) . . ?
C11 C6 C5 119.79(12) . . ?
C7 C6 C5 120.99(12) . . ?
N1 C3 C2 120.79(11) . . ?
N1 C3 C4 111.14(11) . . ?
C2 C3 C4 127.80(11) . . ?
C3 C4 C5 102.08(10) . . ?
C3 C4 H4A 111.7(9) . . ?
C5 C4 H4A 111.4(10) . . ?
C3 C4 H4B 109.7(9) . . ?
C5 C4 H4B 111.4(9) . . ?
H4A C4 H4B 110.3(13) . . ?
O4 C5 C6 108.08(10) . . ?
O4 C5 C4 104.47(10) . . ?
C6 C5 C4 116.30(10) . . ?
O4 C5 H5 106.3(8) . . ?
C6 C5 H5 109.9(8) . . ?
C4 C5 H5 111.1(8) . . ?
O2 C2 O1 124.80(13) . . ?
O2 C2 C3 126.64(13) . . ?
O1 C2 C3 108.55(10) . . ?
C6 C11 C10 120.40(14) . . ?
C6 C11 H11 119.3(11) . . ?
C10 C11 H11 120.3(11) . . ?
C8 C7 C6 119.94(14) . . ?
C8 C7 H7 119.9(10) . . ?
C6 C7 H7 120.1(10) . . ?
C9 C10 C11 120.04(15) . . ?
C9 C10 H10 121.4(13) . . ?
C11 C10 H10 118.5(13) . . ?
C9 C8 C7 120.21(16) . . ?
C9 C8 H8 119.9(13) . . ?
C7 C8 H8 119.9(13) . . ?
O1 C1 H1C 109.4(14) . . ?
O1 C1 H1A 104.2(13) . . ?
H1C C1 H1A 107.4(18) . . ?
O1 C1 H1B 111.4(15) . . ?
H1C C1 H1B 111(2) . . ?
H1A C1 H1B 114(2) . . ?
C10 C9 C8 120.18(15) . . ?
C10 C9 H9 120.5(11) . . ?
C8 C9 H9 119.3(11) . . ?

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
C5 O4 N1 O3 169.35(10) . . . . ?
C5 O4 N1 C3 -13.15(12) . . . . ?
O3 N1 C3 C2 1.7(2) . . . . ?
O4 N1 C3 C2 -175.11(10) . . . . ?
O3 N1 C3 C4 176.15(13) . . . . ?
O4 N1 C3 C4 -0.70(14) . . . . ?
N1 C3 C4 C5 13.48(14) . . . . ?
C2 C3 C4 C5 -172.60(11) . . . . ?
N1 O4 C5 C6 145.09(9) . . . . ?
N1 O4 C5 C4 20.65(12) . . . . ?
C11 C6 C5 O4 115.06(12) . . . . ?
C7 C6 C5 O4 -65.51(15) . . . . ?
C11 C6 C5 C4 -127.91(13) . . . . ?
C7 C6 C5 C4 51.52(17) . . . . ?
C3 C4 C5 O4 -20.35(12) . . . . ?
C3 C4 C5 C6 -139.37(11) . . . . ?
C1 O1 C2 O2 4.6(2) . . . . ?
C1 O1 C2 C3 -174.66(12) . . . . ?
N1 C3 C2 O2 -2.5(2) . . . . ?
C4 C3 C2 O2 -175.89(13) . . . . ?
N1 C3 C2 O1 176.70(11) . . . . ?
C4 C3 C2 O1 3.30(17) . . . . ?
C7 C6 C11 C10 -0.7(2) . . . . ?
C5 C6 C11 C10 178.70(13) . . . . ?
C11 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 -179.59(14) . . . . ?
C6 C11 C10 C9 1.0(2) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C11 C10 C9 C8 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.035



