# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_tamal1_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc29zhqj
_database_code_depnum_ccdc_archive 'CCDC 2144478'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N O6'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.26

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   25.911(4)
_cell_length_b                   4.6748(7)
_cell_length_c                   23.299(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.436(2)
_cell_angle_gamma                90
_cell_volume                     2733.1(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2128
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13697
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.105
_diffrn_reflns_theta_max         28.315
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3406
_reflns_number_gt                2507
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0398P)²+2.2478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1221
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25079(6) 0.9388(3) 0.56471(6) 0.0386(4) Uani 1 1 d . . . . .
O2 O 0.27698(5) 1.0680(3) 0.65632(6) 0.0289(3) Uani 1 1 d . . . . .
O3 O 0.47994(5) 0.2365(3) 0.53522(5) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.51914(5) 0.6405(3) 0.57555(5) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.515505 0.686599 0.539914 0.033 Uiso 1 1 calc R U . . .
O5 O 0.56117(5) -0.0682(3) 0.70282(5) 0.0209(3) Uani 1 1 d . . . . .
O6 O 0.58933(5) 0.1475(3) 0.62956(5) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.28099(6) 0.9198(3) 0.61434(7) 0.0234(3) Uani 1 1 d . . . . .
C1 C 0.32476(6) 0.7111(4) 0.62333(7) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.33096(7) 0.5520(4) 0.57555(8) 0.0228(4) Uani 1 1 d . . . . .
H2A H 0.306933 0.572882 0.537656 0.027 Uiso 1 1 calc R U . . .
C3 C 0.37306(7) 0.3615(4) 0.58430(8) 0.0226(4) Uani 1 1 d . . . . .
H3 H 0.378025 0.250237 0.551971 0.027 Uiso 1 1 calc R U . . .
C4 C 0.40841(7) 0.3304(4) 0.64007(7) 0.0191(4) Uani 1 1 d . . . . .
C5 C 0.40008(7) 0.4931(4) 0.68691(7) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.423648 0.472163 0.725074 0.025 Uiso 1 1 calc R U . . .
C6 C 0.35834(7) 0.6845(4) 0.67921(8) 0.0205(4) Uani 1 1 d . . . . .
H6 H 0.352897 0.794698 0.711462 0.025 Uiso 1 1 calc R U . . .
C7 C 0.45558(7) 0.1313(4) 0.64884(8) 0.0239(4) Uani 1 1 d . . . . .
H7A H 0.446703 -0.027646 0.619978 0.029 Uiso 1 1 calc R U . . .
H7B H 0.462889 0.048115 0.689146 0.029 Uiso 1 1 calc R U . . .
C8 C 0.50503(6) 0.2812(4) 0.64113(7) 0.0185(4) Uani 1 1 d . . . . .
H8 H 0.510241 0.454621 0.667059 0.022 Uiso 1 1 calc R U . . .
C9 C 0.49999(6) 0.3831(4) 0.57828(7) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.55462(6) 0.0956(4) 0.66171(7) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.63840(7) -0.0247(4) 0.64099(8) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.631679 -0.217411 0.656316 0.029 Uiso 1 1 calc R U . . .
C12 C 0.68118(7) 0.1275(5) 0.68641(9) 0.0309(5) Uani 1 1 d . . . . .
H12A H 0.688829 0.312297 0.670480 0.046 Uiso 1 1 calc R U . . .
H12B H 0.713593 0.010573 0.695828 0.046 Uiso 1 1 calc R U . . .
H12C H 0.668928 0.158523 0.722465 0.046 Uiso 1 1 calc R U . . .
C13 C 0.65077(8) -0.0558(5) 0.58148(9) 0.0385(5) Uani 1 1 d . . . . .
H13A H 0.620784 -0.149231 0.553797 0.058 Uiso 1 1 calc R U . . .
H13B H 0.682950 -0.172226 0.585658 0.058 Uiso 1 1 calc R U . . .
H13C H 0.656615 0.133682 0.566270 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.2273(19) . ?
O2 N1 1.224(2) . ?
O3 C9 1.219(2) . ?
O4 C9 1.309(2) . ?
O4 H4 0.8400 . ?
O5 C10 1.205(2) . ?
O6 C10 1.329(2) . ?
O6 C11 1.472(2) . ?
N1 C1 1.471(2) . ?
C1 C6 1.379(2) . ?
C1 C2 1.381(2) . ?
C2 C3 1.384(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C7 1.509(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.510(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(2) . ?
C8 C10 1.525(2) . ?
C8 H8 1.0000 . ?
C11 C13 1.506(3) . ?
C11 C12 1.507(3) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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 O4 H4 109.5 . . ?
C10 O6 C11 118.27(13) . . ?
O2 N1 O1 123.41(16) . . ?
O2 N1 C1 118.54(15) . . ?
O1 N1 C1 118.05(15) . . ?
C6 C1 C2 122.65(16) . . ?
C6 C1 N1 118.47(16) . . ?
C2 C1 N1 118.87(15) . . ?
C1 C2 C3 118.29(16) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 C4 120.91(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.58(16) . . ?
C5 C4 C7 120.67(16) . . ?
C3 C4 C7 120.72(16) . . ?
C6 C5 C4 121.51(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 118.06(16) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C4 C7 C8 112.36(15) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 C9 112.94(14) . . ?
C7 C8 C10 111.84(14) . . ?
C9 C8 C10 110.23(13) . . ?
C7 C8 H8 107.2 . . ?
C9 C8 H8 107.2 . . ?
C10 C8 H8 107.2 . . ?
O3 C9 O4 124.43(15) . . ?
O3 C9 C8 122.38(15) . . ?
O4 C9 C8 113.19(14) . . ?
O5 C10 O6 125.69(15) . . ?
O5 C10 C8 123.52(15) . . ?
O6 C10 C8 110.76(13) . . ?
O6 C11 C13 104.99(14) . . ?
O6 C11 C12 108.65(15) . . ?
C13 C11 C12 113.84(17) . . ?
O6 C11 H11 109.7 . . ?
C13 C11 H11 109.7 . . ?
C12 C11 H11 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.493
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_tamal3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2173993'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2022-05-20 deposited with the CCDC.	2022-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 O4'
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.5868(15)
_cell_length_b                   8.2313(18)
_cell_length_c                   11.126(3)
_cell_angle_alpha                106.015(3)
_cell_angle_beta                 97.159(3)
_cell_angle_gamma                95.387(3)
_cell_volume                     570.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1528
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.21

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.650
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6051
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         28.325
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2827
_reflns_number_gt                1873
_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 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0525P)²+0.0367P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2827
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.74681(15) 0.56505(12) 0.48030(9) 0.0502(3) Uani 1 1 d . . . . .
O2 O 0.98135(15) 0.76142(13) 0.43271(10) 0.0562(3) Uani 1 1 d . . . . .
O3 O 0.64644(17) 0.30853(13) 0.34795(10) 0.0588(3) Uani 1 1 d . . . . .
O4 O 1.11153(18) 0.69097(16) 0.25565(12) 0.0752(4) Uani 1 1 d . . . . .
C1 C 0.8003(2) 0.74299(18) 0.49158(14) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.7204(2) 0.45273(18) 0.36366(14) 0.0461(3) Uani 1 1 d . . . . .
C3 C 0.8067(2) 0.51827(18) 0.26644(14) 0.0459(3) Uani 1 1 d . . . . .
C4 C 0.9792(2) 0.6614(2) 0.31414(15) 0.0535(4) Uani 1 1 d . . . . .
C5 C 0.6236(3) 0.8119(2) 0.43253(16) 0.0592(4) Uani 1 1 d . . . . .
H5A H 0.588427 0.749717 0.344370 0.089 Uiso 1 1 calc R U . . .
H5B H 0.662656 0.930331 0.441141 0.089 Uiso 1 1 calc R U . . .
H5C H 0.506404 0.799635 0.474253 0.089 Uiso 1 1 calc R U . . .
C6 C 0.8647(3) 0.8312(2) 0.63006(16) 0.0654(5) Uani 1 1 d . . . . .
H6A H 0.752796 0.813319 0.674626 0.098 Uiso 1 1 calc R U . . .
H6B H 0.900321 0.951189 0.642819 0.098 Uiso 1 1 calc R U . . .
H6C H 0.982189 0.785624 0.661502 0.098 Uiso 1 1 calc R U . . .
C7 C 0.7465(2) 0.45643(18) 0.14119(14) 0.0511(4) Uani 1 1 d . . . . .
H7 H 0.831901 0.496602 0.092108 0.061 Uiso 1 1 calc R U . . .
C8 C 0.5669(2) 0.33526(18) 0.07023(13) 0.0495(4) Uani 1 1 d . . . . .
C9 C 0.5810(3) 0.2256(2) -0.04765(15) 0.0642(5) Uani 1 1 d . . . . .
H9 H 0.704176 0.229331 -0.080174 0.077 Uiso 1 1 calc R U . . .
C10 C 0.4111(4) 0.1108(2) -0.11646(16) 0.0800(6) Uani 1 1 d . . . . .
H10 H 0.421955 0.034192 -0.193642 0.096 Uiso 1 1 calc R U . . .
C11 C 0.2273(4) 0.1098(3) -0.0710(2) 0.0839(6) Uani 1 1 d . . . . .
H11 H 0.113600 0.032857 -0.117763 0.101 Uiso 1 1 calc R U . . .
C12 C 0.2098(3) 0.2210(2) 0.04225(19) 0.0741(5) Uani 1 1 d . . . . .
H12 H 0.083455 0.221395 0.071353 0.089 Uiso 1 1 calc R U . . .
C13 C 0.3781(2) 0.3324(2) 0.11362(15) 0.0575(4) Uani 1 1 d . . . . .
H13 H 0.365570 0.406340 0.191525 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3493(17) . ?
O1 C1 1.4408(17) . ?
O2 C4 1.3460(18) . ?
O2 C1 1.4456(16) . ?
O3 C2 1.1968(16) . ?
O4 C4 1.1966(17) . ?
C1 C6 1.498(2) . ?
C1 C5 1.499(2) . ?
C2 C3 1.484(2) . ?
C3 C7 1.338(2) . ?
C3 C4 1.488(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.459(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.389(2) . ?
C8 C9 1.392(2) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C13 H13 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
C2 O1 C1 117.84(11) . . ?
C4 O2 C1 118.07(11) . . ?
O1 C1 O2 108.50(11) . . ?
O1 C1 C6 106.20(12) . . ?
O2 C1 C6 106.32(12) . . ?
O1 C1 C5 110.94(12) . . ?
O2 C1 C5 111.27(12) . . ?
C6 C1 C5 113.32(13) . . ?
O3 C2 O1 119.50(13) . . ?
O3 C2 C3 125.12(14) . . ?
O1 C2 C3 115.11(12) . . ?
C7 C3 C2 125.59(13) . . ?
C7 C3 C4 118.17(13) . . ?
C2 C3 C4 116.21(13) . . ?
O4 C4 O2 119.63(14) . . ?
O4 C4 C3 124.94(14) . . ?
O2 C4 C3 115.43(12) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C3 C7 C8 129.57(13) . . ?
C3 C7 H7 115.2 . . ?
C8 C7 H7 115.2 . . ?
C13 C8 C9 118.75(15) . . ?
C13 C8 C7 121.91(13) . . ?
C9 C8 C7 119.24(15) . . ?
C10 C9 C8 119.85(18) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.12(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.45(18) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.29(19) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.46(16) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040

