# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_15a
_database_code_depnum_ccdc_archive 'CCDC 1520833'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H13 N O7'
_chemical_formula_sum            'C10 H13 N O7'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         259.21

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'
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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.0454(6)
_cell_length_b                   14.0347(14)
_cell_length_c                   7.1416(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.033(3)
_cell_angle_gamma                90
_cell_volume                     594.73(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    6262
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      30.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            20042
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_av_R_equivalents  0.1169
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.903
_diffrn_reflns_theta_max         30.409
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3515
_reflns_number_gt                2242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.969

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.1462P)²+1.0323P] 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_abs_structure_details 
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1675
_refine_ls_R_factor_gt           0.1101
_refine_ls_wR_factor_ref         0.3029
_refine_ls_wR_factor_gt          0.2694
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.4051(13) 0.5907(6) 0.4801(14) 0.0404(19) Uani 1 1 d . . . . .
H1 H 0.277170 0.614425 0.537862 0.049 Uiso 1 1 calc R U . . .
C2 C 0.4242(14) 0.6498(5) 0.3103(13) 0.0391(18) Uani 1 1 d . . . . .
H2A H 0.362447 0.615277 0.190927 0.047 Uiso 1 1 calc R U . . .
H2B H 0.341188 0.710568 0.311640 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7671(14) 0.6561(5) 0.5045(15) 0.044(2) Uani 1 1 d . . . . .
C4 C 0.6514(14) 0.6012(5) 0.8105(13) 0.041(2) Uani 1 1 d . . . . .
C5 C 0.8802(15) 0.6259(7) 0.9221(15) 0.051(2) Uani 1 1 d . . . . .
H5A H 0.908187 0.694095 0.908800 0.077 Uiso 1 1 calc R U . . .
H5B H 0.994889 0.589083 0.873481 0.077 Uiso 1 1 calc R U . . .
H5C H 0.887075 0.610614 1.057013 0.077 Uiso 1 1 calc R U . . .
C6 C 0.3734(12) 0.4853(5) 0.4344(11) 0.0313(15) Uani 1 1 d . . . . .
H7 H 0.232349 0.476623 0.336850 0.038 Uiso 1 1 calc R U . . .
C7 C 0.3554(12) 0.4270(5) 0.6113(12) 0.0335(16) Uani 1 1 d . . . . .
C8 C 0.1012(16) 0.3800(7) 0.8003(15) 0.050(2) Uani 1 1 d . . . . .
H00E H -0.055782 0.389729 0.813058 0.075 Uiso 1 1 calc R U . . .
H00F H 0.201935 0.402577 0.915857 0.075 Uiso 1 1 calc R U . . .
H00G H 0.127706 0.311989 0.782513 0.075 Uiso 1 1 calc R U . . .
C9 C 0.5409(12) 0.3746(5) 0.2668(10) 0.0280(13) Uani 1 1 d . . . . .
C10 C 0.7387(15) 0.3486(5) 0.1851(13) 0.0388(18) Uani 1 1 d . . . . .
H10A H 0.722962 0.282813 0.138647 0.058 Uiso 1 1 calc R U . . .
H10B H 0.875440 0.354340 0.283375 0.058 Uiso 1 1 calc R U . . .
H10C H 0.749272 0.391513 0.078846 0.058 Uiso 1 1 calc R U . . .
N N 0.6221(10) 0.6070(5) 0.6152(12) 0.046(2) Uani 1 1 d . . . . .
O1 O 0.4950(13) 0.5766(5) 0.8773(11) 0.0564(18) Uani 1 1 d . . . . .
O2 O 0.6617(10) 0.6674(5) 0.3249(10) 0.0508(17) Uani 1 1 d . . . . .
O3 O 0.9602(12) 0.6751(5) 0.5586(12) 0.0612(19) Uani 1 1 d . . . . .
O4 O 0.5042(8) 0.3804(4) 0.7036(8) 0.0329(11) Uani 1 1 d . . . . .
O5 O 0.1441(7) 0.4317(3) 0.6400(7) 0.0273(10) Uani 1 1 d . . . . .
O6 O 0.5641(9) 0.4604(4) 0.3507(8) 0.0351(12) Uani 1 1 d . . . . .
O7 O 0.3783(12) 0.3247(5) 0.2645(10) 0.0539(18) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N 1.490(11) . ?
C1 C2 1.492(12) . ?
C1 C6 1.519(10) . ?
C1 H1 1.0000 . ?
C2 O2 1.441(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O3 1.188(12) . ?
C3 O2 1.328(12) . ?
C3 N 1.460(12) . ?
C4 O1 1.189(11) . ?
C4 N 1.375(13) . ?
C4 C5 1.499(12) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O6 1.440(8) . ?
C6 C7 1.526(11) . ?
C6 H7 1.0000 . ?
C7 O4 1.202(10) . ?
C7 O5 1.333(8) . ?
C8 O5 1.421(9) . ?
C8 H00E 0.9800 . ?
C8 H00F 0.9800 . ?
C8 H00G 0.9800 . ?
C9 O7 1.204(9) . ?
C9 O6 1.340(9) . ?
C9 C10 1.473(10) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
N C1 C2 104.2(7) . . ?
N C1 C6 110.3(6) . . ?
C2 C1 C6 113.1(8) . . ?
N C1 H1 109.7 . . ?
C2 C1 H1 109.7 . . ?
C6 C1 H1 109.7 . . ?
O2 C2 C1 105.5(7) . . ?
O2 C2 H2A 110.6 . . ?
C1 C2 H2A 110.6 . . ?
O2 C2 H2B 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
O3 C3 O2 123.2(9) . . ?
O3 C3 N 125.8(10) . . ?
O2 C3 N 110.6(7) . . ?
O1 C4 N 117.8(8) . . ?
O1 C4 C5 125.3(10) . . ?
N C4 C5 116.9(8) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O6 C6 C1 104.4(6) . . ?
O6 C6 C7 113.7(6) . . ?
C1 C6 C7 111.7(7) . . ?
O6 C6 H7 108.9 . . ?
C1 C6 H7 108.9 . . ?
C7 C6 H7 108.9 . . ?
O4 C7 O5 125.5(7) . . ?
O4 C7 C6 125.5(7) . . ?
O5 C7 C6 108.8(6) . . ?
O5 C8 H00E 109.5 . . ?
O5 C8 H00F 109.5 . . ?
H00E C8 H00F 109.5 . . ?
O5 C8 H00G 109.5 . . ?
H00E C8 H00G 109.5 . . ?
H00F C8 H00G 109.5 . . ?
O7 C9 O6 122.9(7) . . ?
O7 C9 C10 125.0(7) . . ?
O6 C9 C10 112.1(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N C3 127.1(7) . . ?
C4 N C1 125.0(7) . . ?
C3 N C1 105.5(8) . . ?
C3 O2 C2 109.7(6) . . ?
C7 O5 C8 115.3(6) . . ?
C9 O6 C6 112.4(5) . . ?

_refine_diff_density_max         1.060
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_17a
_database_code_depnum_ccdc_archive 'CCDC 1520834'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H27 N O6 Si'
_chemical_formula_sum            'C19 H27 N O6 Si'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         393.50

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.1774(4)
_cell_length_b                   8.2158(3)
_cell_length_c                   15.0345(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.231(2)
_cell_angle_gamma                90
_cell_volume                     999.67(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9018
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.52
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   SADABS
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42103
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         30.554
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6114
_reflns_number_gt                5766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.0304P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2568 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6114
_refine_ls_number_parameters     252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0288
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.68576(19) 0.20004(19) 0.42655(10) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.7480(2) 0.2299(2) 0.52659(10) 0.0268(4) Uani 1 1 d . . . . .
H2A H 0.723206 0.342131 0.542183 0.040 Uiso 1 1 calc R U . . .
H2B H 0.867622 0.212005 0.538254 0.040 Uiso 1 1 calc R U . . .
H2C H 0.692768 0.154456 0.563133 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4982(2) 0.2316(2) 0.40872(12) 0.0235(3) Uani 1 1 d . . . . .
H3A H 0.441863 0.156661 0.444969 0.035 Uiso 1 1 calc R U . . .
H3B H 0.457840 0.214141 0.344873 0.035 Uiso 1 1 calc R U . . .
H3C H 0.475702 0.344060 0.424988 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7192(2) 0.0211(2) 0.40336(12) 0.0231(3) Uani 1 1 d . . . . .
H4A H 0.837406 -0.002190 0.418622 0.035 Uiso 1 1 calc R U . . .
H4B H 0.685063 0.002926 0.338956 0.035 Uiso 1 1 calc R U . . .
H4C H 0.656258 -0.051068 0.437803 0.035 Uiso 1 1 calc R U . . .
C5 C 1.02209(19) 0.30039(19) 0.37160(11) 0.0196(3) Uani 1 1 d . . . . .
H5A H 1.042682 0.182931 0.370685 0.029 Uiso 1 1 calc R U . . .
H5B H 1.071459 0.345274 0.429672 0.029 Uiso 1 1 calc R U . . .
H5C H 1.071498 0.352909 0.323313 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7535(2) 0.55771(19) 0.37602(11) 0.0209(3) Uani 1 1 d . . . . .
H6A H 0.804413 0.625516 0.333892 0.031 Uiso 1 1 calc R U . . .
H6B H 0.800490 0.585730 0.437765 0.031 Uiso 1 1 calc R U . . .
H6C H 0.633981 0.576854 0.367591 0.031 Uiso 1 1 calc R U . . .
C7 C 0.74445(16) 0.36086(17) 0.17077(9) 0.0119(2) Uani 1 1 d . . . . .
H7 H 0.805757 0.465019 0.185304 0.014 Uiso 1 1 calc R U . . .
C8 C 0.85073(17) 0.24684(18) 0.12256(9) 0.0139(3) Uani 1 1 d . . . . .
C9 C 1.0197(2) 0.2358(3) 0.00800(12) 0.0299(4) Uani 1 1 d . . . . .
H9A H 1.116071 0.193411 0.047484 0.045 Uiso 1 1 calc R U . . .
H9B H 1.056757 0.305350 -0.038185 0.045 Uiso 1 1 calc R U . . .
H9C H 0.954979 0.144894 -0.020806 0.045 Uiso 1 1 calc R U . . .
C10 C 0.57772(17) 0.39862(16) 0.11341(9) 0.0115(2) Uani 1 1 d . . . . .
H10 H 0.510227 0.296717 0.109832 0.014 Uiso 1 1 calc R U . . .
C11 C 0.58649(18) 0.45454(18) 0.01670(9) 0.0148(3) Uani 1 1 d . . . . .
H11A H 0.675172 0.536574 0.016714 0.018 Uiso 1 1 calc R U . . .
H11B H 0.613044 0.360595 -0.019914 0.018 Uiso 1 1 calc R U . . .
C12 C 0.33522(17) 0.49238(17) 0.18588(9) 0.0119(2) Uani 1 1 d . . . . .
C13 C 0.27415(17) 0.65407(16) 0.21089(9) 0.0116(2) Uani 1 1 d . . . . .
C14 C 0.12463(17) 0.69727(18) 0.23700(10) 0.0148(3) Uani 1 1 d . . . . .
H14 H 0.044639 0.617459 0.246147 0.018 Uiso 1 1 calc R U . . .
C15 C 0.09575(18) 0.86246(19) 0.24941(10) 0.0168(3) Uani 1 1 d . . . . .
H15 H -0.006441 0.896248 0.266468 0.020 Uiso 1 1 calc R U . . .
C16 C 0.21485(19) 0.97891(18) 0.23711(10) 0.0161(3) Uani 1 1 d . . . . .
H16 H 0.192009 1.090658 0.245918 0.019 Uiso 1 1 calc R U . . .
C17 C 0.36650(19) 0.93483(17) 0.21220(10) 0.0143(3) Uani 1 1 d . . . . .
H17 H 0.448308 1.013821 0.204784 0.017 Uiso 1 1 calc R U . . .
C18 C 0.39256(17) 0.77050(16) 0.19874(9) 0.0113(2) Uani 1 1 d . . . . .
C19 C 0.53222(16) 0.68622(16) 0.16493(9) 0.0117(2) Uani 1 1 d . . . . .
N N 0.49136(14) 0.52083(14) 0.16015(8) 0.0115(2) Uani 1 1 d . . . . .
O1 O 0.71130(13) 0.28851(13) 0.25103(7) 0.0157(2) Uani 1 1 d . . . . .
O2 O 0.91838(13) 0.33009(16) 0.06048(7) 0.0208(2) Uani 1 1 d . . . . .
O3 O 0.87133(15) 0.10479(14) 0.13845(8) 0.0220(2) Uani 1 1 d . . . . .
O4 O 0.43245(14) 0.52311(14) -0.02142(8) 0.0197(2) Uani 1 1 d . . . . .
H4 H 0.385(2) 0.461(2) -0.0565(16) 0.030 Uiso 1 1 calc R U . . .
O5 O 0.26874(13) 0.36116(13) 0.18550(7) 0.0177(2) Uani 1 1 d . . . . .
O6 O 0.65754(13) 0.74417(13) 0.14354(7) 0.0163(2) Uani 1 1 d . . . . .
Si Si 0.79462(5) 0.33858(5) 0.35468(2) 0.01243(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.537(2) . ?
C1 C3 1.540(2) . ?
C1 C4 1.544(2) . ?
C1 Si 1.8791(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 Si 1.8675(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 Si 1.8676(16) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 O1 1.4059(16) . ?
C7 C8 1.5293(19) . ?
C7 C10 1.5369(19) . ?
C7 H7 1.0000 . ?
C8 O3 1.1983(18) . ?
C8 O2 1.3389(18) . ?
C9 O2 1.4480(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N 1.4638(17) . ?
C10 C11 1.5364(19) . ?
C10 H10 1.0000 . ?
C11 O4 1.4233(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O5 1.2070(17) . ?
C12 N 1.4057(18) . ?
C12 C13 1.4863(19) . ?
C13 C14 1.383(2) . ?
C13 C18 1.3916(19) . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3862(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.4861(19) . ?
C19 O6 1.2144(17) . ?
C19 N 1.3987(17) . ?
O1 Si 1.6606(11) . ?
O4 H4 0.79(3) . ?

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 C1 C3 108.98(13) . . ?
C2 C1 C4 109.16(13) . . ?
C3 C1 C4 108.96(13) . . ?
C2 C1 Si 110.40(11) . . ?
C3 C1 Si 109.86(11) . . ?
C4 C1 Si 109.46(10) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si C5 H5A 109.5 . . ?
Si C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si C6 H6A 109.5 . . ?
Si C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 109.89(11) . . ?
O1 C7 C10 107.60(11) . . ?
C8 C7 C10 112.11(11) . . ?
O1 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
C10 C7 H7 109.1 . . ?
O3 C8 O2 125.18(14) . . ?
O3 C8 C7 125.12(14) . . ?
O2 C8 C7 109.70(12) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N C10 C11 109.90(11) . . ?
N C10 C7 108.62(11) . . ?
C11 C10 C7 115.70(11) . . ?
N C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C7 C10 H10 107.4 . . ?
O4 C11 C10 109.93(12) . . ?
O4 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
O4 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
O5 C12 N 124.99(13) . . ?
O5 C12 C13 129.20(13) . . ?
N C12 C13 105.80(11) . . ?
C14 C13 C18 121.39(13) . . ?
C14 C13 C12 130.08(13) . . ?
C18 C13 C12 108.41(12) . . ?
C13 C14 C15 117.47(13) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C14 C15 C16 120.95(13) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 121.46(13) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 116.97(14) . . ?
C18 C17 H17 121.5 . . ?
C16 C17 H17 121.5 . . ?
C17 C18 C13 121.73(14) . . ?
C17 C18 C19 130.20(13) . . ?
C13 C18 C19 107.93(12) . . ?
O6 C19 N 124.87(13) . . ?
O6 C19 C18 128.82(13) . . ?
N C19 C18 106.29(11) . . ?
C19 N C12 111.54(11) . . ?
C19 N C10 124.26(11) . . ?
C12 N C10 122.53(11) . . ?
C7 O1 Si 126.66(9) . . ?
C8 O2 C9 115.62(14) . . ?
C11 O4 H4 109.5 . . ?
O1 Si C5 110.67(6) . . ?
O1 Si C6 109.89(7) . . ?
C5 Si C6 109.81(7) . . ?
O1 Si C1 103.00(6) . . ?
C5 Si C1 111.38(7) . . ?
C6 Si C1 111.92(7) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_21a
_database_code_depnum_ccdc_archive 'CCDC 1520835'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H9 N O5'
_chemical_formula_sum            'C12 H9 N O5'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         247.20

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.2084(14)
_cell_length_b                   5.2477(8)
_cell_length_c                   24.351(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.768(5)
_cell_angle_gamma                90
_cell_volume                     1048.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9549
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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            20958
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         26.435
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4289
_reflns_number_gt                3895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.991

_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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_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)+(0.1169P)²+15.4246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.12(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(6)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21'
_symmetry_int_tables_number      4
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4289
_refine_ls_number_parameters     202
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1589
_refine_ls_R_factor_gt           0.1518
_refine_ls_wR_factor_ref         0.3717
_refine_ls_wR_factor_gt          0.3679
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.151
_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
C1 C 0.2380(15) 0.447(3) 0.1771(5) 0.0180(10) Uani 1 1 d . . . . .
C2 C 0.2167(15) 0.364(3) 0.2348(5) 0.0180(10) Uani 1 1 d . U . . .
C3 C 0.2830(15) 0.466(3) 0.2835(5) 0.0180(10) Uani 1 1 d . U . . .
H3 H 0.349436 0.613691 0.283017 0.022 Uiso 1 1 calc R U . . .
C4 C 0.2486(15) 0.344(3) 0.3316(5) 0.0180(10) Uani 1 1 d . U . . .
H4 H 0.287413 0.414137 0.365311 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1533(15) 0.110(3) 0.3321(5) 0.0180(10) Uani 1 1 d . U . . .
H5 H 0.135235 0.022340 0.365648 0.022 Uiso 1 1 calc R U . . .
C6 C 0.0902(15) 0.018(3) 0.2837(5) 0.0180(10) Uani 1 1 d . U . . .
H6 H 0.023830 -0.130519 0.283326 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1252(15) 0.145(3) 0.2351(5) 0.0180(10) Uani 1 1 d . U . . .
C8 C 0.0762(15) 0.085(3) 0.1770(5) 0.0180(10) Uani 1 1 d . . . . .
C9 C 0.134(2) 0.272(3) 0.0865(6) 0.027(3) Uani 1 1 d . . . . .
H9 H 0.077194 0.109705 0.076458 0.033 Uiso 1 1 calc R U . . .
C10 C 0.024(2) 0.502(3) 0.0614(8) 0.041(4) Uani 1 1 d . . . . .
H10A H -0.090836 0.447041 0.056066 0.050 Uiso 1 1 calc R U . . .
H10B H 0.026765 0.652522 0.085791 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2437(19) 0.439(4) 0.0058(7) 0.037(4) Uani 1 1 d . . . . .
C12 C 0.295(2) 0.273(4) 0.0559(7) 0.040(4) Uani 1 1 d . . . . .
H12 H 0.383665 0.354321 0.078020 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7647(15) 0.415(3) 0.3259(6) 0.0199(9) Uani 1 1 d . U . . .
C14 C 0.7244(15) 0.353(3) 0.2683(5) 0.0199(9) Uani 1 1 d . . . . .
C15 C 0.7611(15) 0.474(3) 0.2194(5) 0.0199(9) Uani 1 1 d . . . . .
H15 H 0.824832 0.624671 0.219156 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7024(15) 0.368(3) 0.1706(6) 0.0199(9) Uani 1 1 d . . . . .
H16 H 0.727023 0.450010 0.136966 0.024 Uiso 1 1 calc R U . . .
C17 C 0.6125(15) 0.156(3) 0.1694(6) 0.0199(9) Uani 1 1 d . . . . .
H17 H 0.576897 0.087513 0.135132 0.024 Uiso 1 1 calc R U . . .
C18 C 0.5687(15) 0.027(3) 0.2203(5) 0.0199(9) Uani 1 1 d . . . . .
H18 H 0.503442 -0.122114 0.220177 0.024 Uiso 1 1 calc R U . . .
C19 C 0.6261(15) 0.132(3) 0.2684(6) 0.0199(9) Uani 1 1 d . . . . .
C20 C 0.6030(15) 0.056(3) 0.3262(5) 0.0199(9) Uani 1 1 d . U . . .
C21 C 0.6861(14) 0.221(2) 0.4186(5) 0.013(2) Uani 1 1 d . U . . .
H21 H 0.612031 0.080529 0.430608 0.016 Uiso 1 1 calc R U . . .
C22 C 0.8634(15) 0.170(3) 0.4428(6) 0.021(3) Uani 1 1 d . . . . .
H22A H 0.886079 -0.015221 0.444983 0.026 Uiso 1 1 calc R U . . .
H22B H 0.946960 0.251475 0.419695 0.026 Uiso 1 1 calc R U . . .
C23 C 0.7391(15) 0.453(3) 0.5009(5) 0.0192(12) Uani 1 1 d . . . . .
C24 C 0.6397(15) 0.462(3) 0.4472(5) 0.0192(12) Uani 1 1 d . . . . .
H24 H 0.681651 0.607541 0.424958 0.023 Uiso 1 1 calc R U . . .
N1 N 0.1531(13) 0.271(2) 0.1444(5) 0.0180(10) Uani 1 1 d . . . . .
N2 N 0.6860(13) 0.231(2) 0.3579(5) 0.0199(9) Uani 1 1 d . U . . .
O1 O 0.3133(12) 0.6276(19) 0.1587(4) 0.023(2) Uani 1 1 d . . . . .
O2 O -0.0084(12) -0.0868(19) 0.1608(4) 0.025(2) Uani 1 1 d . . . . .
O3 O 0.0980(14) 0.555(2) 0.0103(5) 0.039(3) Uani 1 1 d . . . . .
O4 O 0.3295(16) 0.474(4) -0.0365(6) 0.059(4) Uani 1 1 d . . . . .
O5 O 0.3356(17) 0.033(3) 0.0399(5) 0.052(4) Uani 1 1 d . . . . .
H5A H 0.437557 0.018558 0.039634 0.077 Uiso 1 1 calc R U . . .
O6 O 0.8481(10) 0.5932(19) 0.3457(4) 0.0199(9) Uani 1 1 d . . . . .
O7 O 0.5297(11) -0.1290(19) 0.3440(4) 0.0199(9) Uani 1 1 d . . . . .
O8 O 0.8613(11) 0.2827(19) 0.4969(4) 0.0192(12) Uani 1 1 d . . . . .
O9 O 0.7242(10) 0.5815(19) 0.5418(4) 0.0192(12) Uani 1 1 d . . . . .
O10 O 0.4745(10) 0.5064(19) 0.4563(4) 0.022(2) Uani 1 1 d . . . . .
H10 H 0.420966 0.374408 0.448563 0.033 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
C1 O1 1.220(17) . ?
C1 N1 1.398(17) . ?
C1 C2 1.484(18) . ?
C2 C7 1.370(19) . ?
C2 C3 1.405(18) . ?
C3 C4 1.365(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.458(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.499(17) . ?
C8 O2 1.200(16) . ?
C8 N1 1.416(17) . ?
C9 N1 1.417(17) . ?
C9 C12 1.52(2) . ?
C9 C10 1.62(2) . ?
C9 H9 1.0000 . ?
C10 O3 1.42(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O4 1.27(2) . ?
C11 O3 1.35(2) . ?
C11 C12 1.55(3) . ?
C12 O5 1.36(2) . ?
C12 H12 1.0000 . ?
C13 O6 1.250(17) . ?
C13 N2 1.406(17) . ?
C13 C14 1.473(19) . ?
C14 C15 1.385(19) . ?
C14 C19 1.412(19) . ?
C15 C16 1.390(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.337(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.460(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.480(18) . ?
C20 O7 1.224(17) . ?
C20 N2 1.374(18) . ?
C21 N2 1.478(16) . ?
C21 C24 1.498(18) . ?
C21 C22 1.585(16) . ?
C21 H21 1.0000 . ?
C22 O8 1.445(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 O9 1.210(16) . ?
C23 O8 1.350(16) . ?
C23 C24 1.532(18) . ?
C24 O10 1.396(15) . ?
C24 H24 1.0000 . ?
O5 H5A 0.8400 . ?
O10 H10 0.8400 . ?

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
O1 C1 N1 123.7(12) . . ?
O1 C1 C2 130.0(12) . . ?
N1 C1 C2 106.3(11) . . ?
C7 C2 C3 121.3(13) . . ?
C7 C2 C1 108.9(11) . . ?
C3 C2 C1 129.7(12) . . ?
C4 C3 C2 117.7(13) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.2(12) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 119.1(12) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 118.8(13) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 121.7(12) . . ?
C2 C7 C8 108.3(12) . . ?
C6 C7 C8 130.1(12) . . ?
O2 C8 N1 126.5(12) . . ?
O2 C8 C7 128.1(13) . . ?
N1 C8 C7 105.4(11) . . ?
N1 C9 C12 113.7(13) . . ?
N1 C9 C10 115.5(13) . . ?
C12 C9 C10 107.3(13) . . ?
N1 C9 H9 106.6 . . ?
C12 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
O3 C10 C9 103.4(13) . . ?
O3 C10 H10A 111.1 . . ?
C9 C10 H10A 111.1 . . ?
O3 C10 H10B 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.0 . . ?
O4 C11 O3 120.4(16) . . ?
O4 C11 C12 124.8(16) . . ?
O3 C11 C12 114.7(14) . . ?
O5 C12 C9 111.0(15) . . ?
O5 C12 C11 111.1(14) . . ?
C9 C12 C11 99.2(14) . . ?
O5 C12 H12 111.6 . . ?
C9 C12 H12 111.6 . . ?
C11 C12 H12 111.6 . . ?
O6 C13 N2 123.6(12) . . ?
O6 C13 C14 130.3(12) . . ?
N2 C13 C14 106.1(11) . . ?
C15 C14 C19 120.4(13) . . ?
C15 C14 C13 132.0(13) . . ?
C19 C14 C13 107.5(12) . . ?
C14 C15 C16 118.4(13) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 122.4(13) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 120.5(13) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 117.0(13) . . ?
C19 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C18 C19 C14 121.2(13) . . ?
C18 C19 C20 131.0(13) . . ?
C14 C19 C20 107.7(12) . . ?
O7 C20 N2 125.0(12) . . ?
O7 C20 C19 128.5(12) . . ?
N2 C20 C19 106.5(11) . . ?
N2 C21 C24 116.0(11) . . ?
N2 C21 C22 111.4(10) . . ?
C24 C21 C22 102.0(10) . . ?
N2 C21 H21 109.1 . . ?
C24 C21 H21 109.1 . . ?
C22 C21 H21 109.1 . . ?
O8 C22 C21 104.3(10) . . ?
O8 C22 H22A 110.9 . . ?
C21 C22 H22A 110.9 . . ?
O8 C22 H22B 110.9 . . ?
C21 C22 H22B 110.9 . . ?
H22A C22 H22B 108.9 . . ?
O9 C23 O8 120.8(12) . . ?
O9 C23 C24 128.9(12) . . ?
O8 C23 C24 110.2(11) . . ?
O10 C24 C21 117.9(11) . . ?
O10 C24 C23 112.2(11) . . ?
C21 C24 C23 103.6(11) . . ?
O10 C24 H24 107.5 . . ?
C21 C24 H24 107.5 . . ?
C23 C24 H24 107.5 . . ?
C1 N1 C8 111.1(11) . . ?
C1 N1 C9 127.8(12) . . ?
C8 N1 C9 121.0(12) . . ?
C20 N2 C13 112.1(11) . . ?
C20 N2 C21 122.1(11) . . ?
C13 N2 C21 125.8(11) . . ?
C11 O3 C10 112.0(13) . . ?
C12 O5 H5A 109.5 . . ?
C23 O8 C22 110.9(10) . . ?
C24 O10 H10 109.5 . . ?

_refine_diff_density_max         1.245
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.201

