# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_mo_023RB143_0m
_database_code_depnum_ccdc_archive 'CCDC 1539385'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H12 N2, C4 H O4, 0.5(C4 O4), 2(H2 O)'
_chemical_formula_sum            'C13 H17 N2 O8'
_chemical_formula_weight         329.28

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/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                   4.7188(6)
_cell_length_b                   15.4660(14)
_cell_length_c                   20.0360(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.372(4)
_cell_angle_gamma                90
_cell_volume                     1442.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4055
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      23.23

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.641
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5635
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean photon
_diffrn_reflns_number            12685
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         23.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.790
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.790
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.790
_reflns_number_total             2071
_reflns_number_gt                1674
_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.
 The poor quality of reflections could be due to the fact
 that the crystal does not diffract very well. 
 Other attempts of crystallization were done, but no single
 crystals of better quality were obtained. 
 
 _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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_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)+(0.0490P)²+0.4066P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2071
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
N1 N 0.3234(3) -0.37757(9) -0.13314(7) 0.0130(4) Uani 1 1 d . . . . .
H1N H 0.4805 -0.3783 -0.1027 0.016 Uiso 1 1 d R U . . .
N2 N 0.2740(4) -0.08579(10) -0.06146(8) 0.0210(4) Uani 1 1 d . . . . .
H1 H 0.1420 -0.0523 -0.0452 0.025 Uiso 1 1 d R U . . .
H2 H 0.3436 -0.0568 -0.0949 0.025 Uiso 1 1 d R U . . .
H2N H 0.4208 -0.0982 -0.0274 0.025 Uiso 1 1 d R U . . .
C7 C 0.2103(4) -0.45332(12) -0.15772(9) 0.0160(5) Uani 1 1 d . . . . .
H7 H 0.2966 -0.5051 -0.1420 0.019 Uiso 1 1 calc R U . . .
C8 C -0.0322(5) -0.45411(12) -0.20590(9) 0.0186(5) Uani 1 1 d . . . . .
H8 H -0.1115 -0.5062 -0.2230 0.022 Uiso 1 1 calc R U . . .
C9 C -0.1571(4) -0.37651(12) -0.22873(10) 0.0173(5) Uani 1 1 d . . . . .
H9 H -0.3205 -0.3759 -0.2617 0.021 Uiso 1 1 calc R U . . .
C10 C -0.0379(4) -0.29992(12) -0.20226(9) 0.0157(5) Uani 1 1 d . . . . .
H10 H -0.1213 -0.2475 -0.2173 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2054(4) -0.30095(11) -0.15338(9) 0.0113(4) Uani 1 1 d . . . . .
C12 C 0.3476(4) -0.22103(11) -0.12170(9) 0.0140(4) Uani 1 1 d . . . . .
H12 H 0.4190 -0.1867 -0.1559 0.017 Uiso 1 1 calc R U . . .
H12A H 0.5098 -0.2370 -0.0877 0.017 Uiso 1 1 calc R U . . .
C13 C 0.1361(4) -0.16772(12) -0.08912(10) 0.0173(5) Uani 1 1 d . . . . .
H13 H -0.0315 -0.1546 -0.1225 0.021 Uiso 1 1 calc R U . . .
H13A H 0.0737 -0.2007 -0.0529 0.021 Uiso 1 1 calc R U . . .
O1 O -0.5447(3) -0.22969(8) -0.46057(6) 0.0152(3) Uani 1 1 d . . . . .
H1O H -0.5721 -0.1666 -0.4533 0.023 Uiso 1 1 d R U . . .
O2 O -0.2160(3) -0.40679(8) -0.46987(6) 0.0175(3) Uani 1 1 d . . . . .
O3 O 0.2802(3) -0.34974(8) -0.34454(6) 0.0188(3) Uani 1 1 d . . . . .
O4 O -0.0411(3) -0.16499(8) -0.33731(6) 0.0179(3) Uani 1 1 d . . . . .
C1 C -0.3056(4) -0.26008(11) -0.42732(9) 0.0129(4) Uani 1 1 d . . . . .
C2 C -0.1656(4) -0.34134(12) -0.43257(9) 0.0134(5) Uani 1 1 d . . . . .
C3 C 0.0626(4) -0.31557(12) -0.37653(9) 0.0136(5) Uani 1 1 d . . . . .
C4 C -0.0860(4) -0.23126(12) -0.37308(9) 0.0137(4) Uani 1 1 d . . . . .
O5 O 1.1842(3) -0.62618(8) 0.04881(6) 0.0149(3) Uani 1 1 d . . . . .
O6 O 0.6157(3) -0.57300(8) -0.05868(6) 0.0173(3) Uani 1 1 d . . . . .
C5 C 1.0847(4) -0.55702(12) 0.02197(9) 0.0121(4) Uani 1 1 d . . . . .
C6 C 0.8290(4) -0.53354(12) -0.02599(9) 0.0130(5) Uani 1 1 d . . . . .
O1W O 0.5095(3) -0.12648(8) -0.26721(6) 0.0196(3) Uani 1 1 d . . . . .
H1W H 0.3523 -0.1412 -0.2889 0.029 Uiso 1 1 d R U . . .
H3 H 0.6473 -0.1325 -0.2942 0.029 Uiso 1 1 d R U . . .
O2W O 0.6101(3) -0.02329(8) -0.15184(7) 0.0285(4) Uani 1 1 d . . . . .
H2W H 0.6513 0.0301 -0.1533 0.043 Uiso 1 1 d R U . . .
H4 H 0.6040 -0.0445 -0.1911 0.043 Uiso 1 1 d 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
N1 C11 1.344(2) . ?
N1 C7 1.347(2) . ?
N1 H1N 0.8799 . ?
N2 C13 1.490(2) . ?
N2 H1 0.9100 . ?
N2 H2 0.9101 . ?
N2 H2N 0.9099 . ?
C7 C8 1.372(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.497(3) . ?
C12 C13 1.521(3) . ?
C12 H12 0.9700 . ?
C12 H12A 0.9700 . ?
C13 H13 0.9700 . ?
C13 H13A 0.9700 . ?
O1 C1 1.301(2) . ?
O1 H1O 0.9983 . ?
O2 C2 1.258(2) . ?
O3 C3 1.237(2) . ?
O4 C4 1.249(2) . ?
C1 C2 1.432(3) . ?
C1 C4 1.445(3) . ?
C2 C3 1.478(3) . ?
C3 C4 1.487(3) . ?
O5 C5 1.254(2) . ?
O6 C6 1.265(2) . ?
C5 C6 1.457(3) 3_745 ?
C5 C6 1.461(3) . ?
C6 C5 1.457(3) 3_745 ?
O1W H1W 0.8283 . ?
O1W H3 0.9158 . ?
O2W H2W 0.8504 . ?
O2W H4 0.8476 . ?

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
C11 N1 C7 122.46(17) . . ?
C11 N1 H1N 118.8 . . ?
C7 N1 H1N 118.8 . . ?
C13 N2 H1 109.5 . . ?
C13 N2 H2 109.4 . . ?
H1 N2 H2 109.5 . . ?
C13 N2 H2N 109.5 . . ?
H1 N2 H2N 109.5 . . ?
H2 N2 H2N 109.5 . . ?
N1 C7 C8 120.03(17) . . ?
N1 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 119.16(18) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 119.54(19) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.13(18) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
N1 C11 C10 118.66(16) . . ?
N1 C11 C12 117.71(17) . . ?
C10 C11 C12 123.64(16) . . ?
C11 C12 C13 110.43(16) . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
H12 C12 H12A 108.1 . . ?
N2 C13 C12 110.08(16) . . ?
N2 C13 H13 109.6 . . ?
C12 C13 H13 109.6 . . ?
N2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
H13 C13 H13A 108.2 . . ?
C1 O1 H1O 113.6 . . ?
O1 C1 C2 130.65(18) . . ?
O1 C1 C4 136.88(17) . . ?
C2 C1 C4 92.46(16) . . ?
O2 C2 C1 134.86(19) . . ?
O2 C2 C3 135.41(18) . . ?
C1 C2 C3 89.73(15) . . ?
O3 C3 C2 135.96(18) . . ?
O3 C3 C4 135.09(18) . . ?
C2 C3 C4 88.92(15) . . ?
O4 C4 C1 135.94(18) . . ?
O4 C4 C3 135.17(18) . . ?
C1 C4 C3 88.88(15) . . ?
O5 C5 C6 135.62(18) . 3_745 ?
O5 C5 C6 134.90(17) . . ?
C6 C5 C6 89.47(15) 3_745 . ?
O6 C6 C5 133.15(18) . 3_745 ?
O6 C6 C5 136.32(17) . . ?
C5 C6 C5 90.53(15) 3_745 . ?
H1W O1W H3 108.9 . . ?
H2W O2W H4 108.5 . . ?

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
C11 N1 C7 C8 0.9(3) . . . . ?
N1 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C7 N1 C11 C10 -1.4(2) . . . . ?
C7 N1 C11 C12 179.06(16) . . . . ?
C9 C10 C11 N1 0.8(3) . . . . ?
C9 C10 C11 C12 -179.63(17) . . . . ?
N1 C11 C12 C13 -123.25(17) . . . . ?
C10 C11 C12 C13 57.2(2) . . . . ?
C11 C12 C13 N2 -176.53(15) . . . . ?
O1 C1 C2 O2 2.3(3) . . . . ?
C4 C1 C2 O2 -178.7(2) . . . . ?
O1 C1 C2 C3 -178.22(19) . . . . ?
C4 C1 C2 C3 0.81(14) . . . . ?
O2 C2 C3 O3 -3.0(4) . . . . ?
C1 C2 C3 O3 177.5(2) . . . . ?
O2 C2 C3 C4 178.7(2) . . . . ?
C1 C2 C3 C4 -0.79(13) . . . . ?
O1 C1 C4 O4 -0.5(4) . . . . ?
C2 C1 C4 O4 -179.4(2) . . . . ?
O1 C1 C4 C3 178.1(2) . . . . ?
C2 C1 C4 C3 -0.81(14) . . . . ?
O3 C3 C4 O4 1.2(4) . . . . ?
C2 C3 C4 O4 179.4(2) . . . . ?
O3 C3 C4 C1 -177.5(2) . . . . ?
C2 C3 C4 C1 0.78(13) . . . . ?
O5 C5 C6 O6 -0.8(4) . . . . ?
C6 C5 C6 O6 -180.0(3) 3_745 . . . ?
O5 C5 C6 C5 179.1(3) . . . 3_745 ?
C6 C5 C6 C5 -0.003(0) 3_745 . . 3_745 ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_mo_023SB127B_0ma_aa
_audit_block_doi                 10.5517/cc13597t
_database_code_depnum_ccdc_archive 'CCDC 1017985'
_audit_update_record             
;
2014-08-05 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '5(C20 H20 N2 O4), 4(C2 H6 O S), 2(H2 O)'
_chemical_formula_sum            'C108 H128 N10 O26 S4'
_chemical_formula_weight         2110.44

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'
S S 0.1246 0.1234 '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                   23.485(10)
_cell_length_b                   9.632(4)
_cell_length_c                   47.030(19)
_cell_angle_alpha                90
_cell_angle_beta                 96.764(10)
_cell_angle_gamma                90
_cell_volume                     10564(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    9915
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      21.83

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             4472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.189
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            173437
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         2.159
_diffrn_reflns_theta_max         29.115
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             27354
_reflns_number_gt                6230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)]
 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         27354
_refine_ls_number_parameters     1353
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.3231
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0520
_refine_ls_goodness_of_fit_ref   0.703
_refine_ls_restrained_S_all      0.704
_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
O1A O 0.91572(8) 0.74255(18) 0.19804(3) 0.0638(6) Uani 1 1 d . . . . .
H1AO H 0.9298 0.8154 0.2046 0.096 Uiso 1 1 calc R U . . .
O2A O 0.93025(8) 1.01517(18) 0.03334(4) 0.0526(6) Uani 1 1 d . U . . .
O3A O 0.88179(8) 1.11559(17) -0.03080(3) 0.0526(6) Uani 1 1 d . U . . .
O4A O 0.72258(8) 1.03899(17) -0.19561(3) 0.0650(6) Uani 1 1 d . . . . .
H4AO H 0.7474 1.0935 -0.1994 0.098 Uiso 1 1 calc R U . . .
N1A N 0.82161(8) 0.8028(2) 0.03325(4) 0.0393(6) Uani 1 1 d . . . . .
H1AA H 0.7921 0.7529 0.0275 0.047 Uiso 1 1 calc R U . . .
N2A N 0.77361(9) 0.9042(2) -0.03078(4) 0.0375(6) Uani 1 1 d . . . . .
H2AN H 0.7484 0.8492 -0.0252 0.045 Uiso 1 1 calc R U . . .
C1A C 0.87321(12) 0.9008(3) 0.12812(6) 0.0465(9) Uani 1 1 d . . . . .
H1A H 0.8795 0.9822 0.1183 0.056 Uiso 1 1 calc R U . . .
C2A C 0.89888(12) 0.8833(3) 0.15552(6) 0.0492(9) Uani 1 1 d . . . . .
H2A H 0.9223 0.9530 0.1641 0.059 Uiso 1 1 calc R U . . .
C3A C 0.89054(13) 0.7643(4) 0.17044(6) 0.0440(9) Uani 1 1 d . . . . .
C4A C 0.85491(13) 0.6629(3) 0.15764(7) 0.0519(10) Uani 1 1 d . . . . .
H4A H 0.8479 0.5826 0.1676 0.062 Uiso 1 1 calc R U . . .
C5A C 0.82986(12) 0.6811(3) 0.13007(6) 0.0448(9) Uani 1 1 d . . . . .
H5A H 0.8066 0.6110 0.1215 0.054 Uiso 1 1 calc R U . . .
C6A C 0.83793(12) 0.7992(3) 0.11467(6) 0.0389(8) Uani 1 1 d . . . . .
C7A C 0.81005(10) 0.8178(2) 0.08455(5) 0.0457(8) Uani 1 1 d . . . . .
H7AA H 0.7977 0.9136 0.0820 0.055 Uiso 1 1 calc R U . . .
H7AB H 0.7762 0.7596 0.0816 0.055 Uiso 1 1 calc R U . . .
C8A C 0.84886(10) 0.7823(2) 0.06215(5) 0.0375(8) Uani 1 1 d . . . . .
H8AA H 0.8830 0.8395 0.0651 0.045 Uiso 1 1 calc R U . . .
H8AB H 0.8607 0.6861 0.0645 0.045 Uiso 1 1 calc R U . . .
C9A C 0.83921(12) 0.8932(3) 0.01526(6) 0.0319(8) Uani 1 1 d . . . . .
C10A C 0.88883(12) 0.9857(3) 0.01592(6) 0.0371(8) Uani 1 1 d . U . . .
C11A C 0.86608(12) 1.0319(3) -0.01329(5) 0.0378(8) Uani 1 1 d . U . . .
C12A C 0.81840(12) 0.9359(3) -0.01269(6) 0.0320(8) Uani 1 1 d . . . . .
C13A C 0.76433(11) 0.9572(2) -0.05989(5) 0.0387(8) Uani 1 1 d . . . . .
H13A H 0.7925 1.0285 -0.0623 0.046 Uiso 1 1 calc R U . . .
H13B H 0.7266 0.9991 -0.0632 0.046 Uiso 1 1 calc R U . . .
C14A C 0.76898(11) 0.8431(2) -0.08141(5) 0.0441(8) Uani 1 1 d . . . . .
H14A H 0.8071 0.8029 -0.0782 0.053 Uiso 1 1 calc R U . . .
H14B H 0.7416 0.7707 -0.0784 0.053 Uiso 1 1 calc R U . . .
C15A C 0.75815(14) 0.8927(3) -0.11187(6) 0.0391(8) Uani 1 1 d . . . . .
C16A C 0.80102(12) 0.9425(3) -0.12659(6) 0.0451(9) Uani 1 1 d . . . . .
H16A H 0.8384 0.9447 -0.1175 0.054 Uiso 1 1 calc R U . . .
C17A C 0.79040(13) 0.9891(3) -0.15425(6) 0.0451(9) Uani 1 1 d . . . . .
H17A H 0.8206 1.0208 -0.1637 0.054 Uiso 1 1 calc R U . . .
C18A C 0.73628(15) 0.9893(3) -0.16801(6) 0.0439(9) Uani 1 1 d . . . . .
C19A C 0.69228(12) 0.9383(3) -0.15409(6) 0.0495(9) Uani 1 1 d . . . . .
H19A H 0.6550 0.9369 -0.1633 0.059 Uiso 1 1 calc R U . . .
C20A C 0.70384(13) 0.8893(3) -0.12642(6) 0.0473(9) Uani 1 1 d . . . . .
H20A H 0.6740 0.8530 -0.1174 0.057 Uiso 1 1 calc R U . . .
O1B O 0.87668(8) 0.17648(18) 0.20028(3) 0.0721(7) Uani 1 1 d . . . . .
H1BO H 0.9086 0.1414 0.2036 0.087 Uiso 1 1 calc R U . . .
O2B O 0.71865(7) 0.08556(17) 0.03450(3) 0.0499(6) Uani 1 1 d . U . . .
O3B O 0.66898(7) 0.19016(17) -0.02931(3) 0.0478(6) Uani 1 1 d . U . . .
O4B O 0.72554(7) 0.49213(17) -0.19543(3) 0.0587(6) Uani 1 1 d . . . . .
H4BO H 0.7464 0.5549 -0.1998 0.088 Uiso 1 1 calc R U . . .
N1B N 0.82436(9) 0.3056(2) 0.03496(4) 0.0404(7) Uani 1 1 d . . . . .
H1BN H 0.8485 0.3635 0.0292 0.048 Uiso 1 1 calc R U . . .
N2B N 0.77377(8) 0.41140(19) -0.02800(4) 0.0351(6) Uani 1 1 d . . . . .
H2BN H 0.8015 0.4655 -0.0217 0.042 Uiso 1 1 calc R U . . .
C1B C 0.90089(13) 0.3121(3) 0.12995(6) 0.0446(9) Uani 1 1 d . . . . .
H1B H 0.9308 0.3424 0.1202 0.054 Uiso 1 1 calc R U . . .
C2B C 0.91301(12) 0.2646(3) 0.15792(6) 0.0499(9) Uani 1 1 d . . . . .
H2B H 0.9505 0.2619 0.1668 0.060 Uiso 1 1 calc R U . . .
C3B C 0.86836(15) 0.2217(3) 0.17215(6) 0.0445(9) Uani 1 1 d . . . . .
C4B C 0.81372(13) 0.2257(3) 0.15913(6) 0.0482(9) Uani 1 1 d . . . . .
H4B H 0.7838 0.1967 0.1690 0.058 Uiso 1 1 calc R U . . .
C5B C 0.80242(11) 0.2723(3) 0.13155(5) 0.0442(8) Uani 1 1 d . . . . .
H5B H 0.7647 0.2747 0.1230 0.053 Uiso 1 1 calc R U . . .
C6B C 0.84554(14) 0.3156(3) 0.11627(6) 0.0363(8) Uani 1 1 d . . . . .
C7B C 0.83472(11) 0.3671(2) 0.08582(5) 0.0480(9) Uani 1 1 d . . . . .
H7BA H 0.7978 0.4131 0.0830 0.058 Uiso 1 1 calc R U . . .
H7BB H 0.8638 0.4350 0.0826 0.058 Uiso 1 1 calc R U . . .
C8B C 0.83546(10) 0.2518(2) 0.06416(5) 0.0414(8) Uani 1 1 d . . . . .
H8BA H 0.8725 0.2062 0.0667 0.050 Uiso 1 1 calc R U . . .
H8BB H 0.8065 0.1834 0.0673 0.050 Uiso 1 1 calc R U . . .
C9B C 0.77987(12) 0.2707(3) 0.01712(6) 0.0298(7) Uani 1 1 d . . . . .
C10B C 0.73322(12) 0.1718(3) 0.01734(5) 0.0320(8) Uani 1 1 d . U . . .
C11B C 0.71038(12) 0.2192(3) -0.01193(6) 0.0342(8) Uani 1 1 d . U . . .
C12B C 0.75789(11) 0.3167(3) -0.01066(5) 0.0282(7) Uani 1 1 d . U . . .
C13B C 0.74760(10) 0.4314(2) -0.05731(5) 0.0373(8) Uani 1 1 d . . . . .
H13C H 0.7439 0.5300 -0.0613 0.045 Uiso 1 1 calc R U . . .
H13D H 0.7095 0.3913 -0.0595 0.045 Uiso 1 1 calc R U . . .
C14B C 0.78271(11) 0.3653(2) -0.07825(5) 0.0546(9) Uani 1 1 d . . . . .
H14C H 0.7810 0.2653 -0.0761 0.066 Uiso 1 1 calc R U . . .
H14D H 0.8224 0.3933 -0.0735 0.066 Uiso 1 1 calc R U . . .
C15B C 0.76399(12) 0.4014(3) -0.10901(6) 0.0395(8) Uani 1 1 d . . . . .
C16B C 0.73175(12) 0.3120(3) -0.12718(6) 0.0415(8) Uani 1 1 d . . . . .
H16B H 0.7186 0.2293 -0.1201 0.050 Uiso 1 1 calc R U . . .
C17B C 0.71874(11) 0.3442(3) -0.15585(6) 0.0430(9) Uani 1 1 d . . . . .
H17B H 0.6976 0.2823 -0.1681 0.052 Uiso 1 1 calc R U . . .
C18B C 0.73670(12) 0.4658(3) -0.16621(6) 0.0372(8) Uani 1 1 d . . . . .
C19B C 0.76650(12) 0.5604(3) -0.14847(6) 0.0455(9) Uani 1 1 d . . . . .
H19B H 0.7769 0.6459 -0.1554 0.055 Uiso 1 1 calc R U . . .
C20B C 0.78064(11) 0.5261(3) -0.12009(6) 0.0442(9) Uani 1 1 d . . . . .
H20B H 0.8020 0.5884 -0.1080 0.053 Uiso 1 1 calc R U . . .
O1C O 0.50585(8) -0.02654(18) 0.19897(4) 0.0759(7) Uani 1 1 d . . . . .
H1CO H 0.5259 0.0412 0.2038 0.114 Uiso 1 1 calc R U . . .
O2C O 0.53121(8) 0.21285(18) 0.03212(4) 0.0513(6) Uani 1 1 d . U . . .
O3C O 0.48261(7) 0.31051(17) -0.03227(3) 0.0468(6) Uani 1 1 d . U . . .
O4C O 0.30357(8) 0.19227(17) -0.19627(3) 0.0698(7) Uani 1 1 d . . . . .
H4CO H 0.3244 0.2528 -0.2017 0.084 Uiso 1 1 calc R U . . .
N1C N 0.42459(8) -0.00513(19) 0.03193(4) 0.0354(6) Uani 1 1 d . U . . .
H1CN H 0.3962 -0.0582 0.0260 0.042 Uiso 1 1 calc R U . . .
N2C N 0.37624(9) 0.0937(2) -0.03194(4) 0.0389(6) Uani 1 1 d . . . . .
H2CN H 0.3513 0.0389 -0.0260 0.047 Uiso 1 1 calc R U . . .
C1C C 0.47018(12) 0.1081(3) 0.12635(6) 0.0457(9) Uani 1 1 d . . . . .
H1C H 0.4759 0.1877 0.1159 0.055 Uiso 1 1 calc R U . . .
C2C C 0.49406(12) 0.0997(3) 0.15453(6) 0.0500(9) Uani 1 1 d . . . . .
H2C H 0.5164 0.1723 0.1627 0.060 Uiso 1 1 calc R U . . .
C3C C 0.48483(14) -0.0153(4) 0.17046(6) 0.0523(10) Uani 1 1 d . . . . .
C4C C 0.45397(14) -0.1234(3) 0.15789(7) 0.0547(10) Uani 1 1 d . . . . .
H4C H 0.4487 -0.2032 0.1684 0.066 Uiso 1 1 calc R U . . .
C5C C 0.43053(12) -0.1151(3) 0.12972(7) 0.0505(9) Uani 1 1 d . . . . .
H5C H 0.4092 -0.1894 0.1215 0.061 Uiso 1 1 calc R U . . .
C6C C 0.43797(12) 0.0011(3) 0.11331(6) 0.0393(8) Uani 1 1 d . . . . .
C7C C 0.41112(11) 0.0125(3) 0.08275(5) 0.0496(9) Uani 1 1 d . . . . .
H7CA H 0.3785 -0.0496 0.0799 0.059 Uiso 1 1 calc R U . . .
H7CB H 0.3970 0.1064 0.0793 0.059 Uiso 1 1 calc R U . . .
C8C C 0.45150(10) -0.0217(2) 0.06123(4) 0.0388(8) Uani 1 1 d . U . . .
H8CA H 0.4848 0.0386 0.0643 0.047 Uiso 1 1 calc R U . . .
H8CB H 0.4646 -0.1167 0.0641 0.047 Uiso 1 1 calc R U . . .
C9C C 0.44157(11) 0.0868(3) 0.01416(5) 0.0296(7) Uani 1 1 d . . . . .
C10C C 0.48921(12) 0.1836(3) 0.01478(6) 0.0338(8) Uani 1 1 d . U . . .
C11C C 0.46764(11) 0.2272(3) -0.01459(5) 0.0337(8) Uani 1 1 d . U . . .
C12C C 0.42066(12) 0.1287(3) -0.01398(6) 0.0322(8) Uani 1 1 d . . . . .
C13C C 0.36645(11) 0.1417(2) -0.06127(5) 0.0379(8) Uani 1 1 d . . . . .
H13E H 0.3926 0.2174 -0.0639 0.046 Uiso 1 1 calc R U . . .
H13F H 0.3276 0.1769 -0.0651 0.046 Uiso 1 1 calc R U . . .
C14C C 0.37507(11) 0.0275(2) -0.08221(5) 0.0518(9) Uani 1 1 d . . . . .
H14E H 0.4151 0.0005 -0.0799 0.062 Uiso 1 1 calc R U . . .
H14F H 0.3527 -0.0528 -0.0778 0.062 Uiso 1 1 calc R U . . .
C15C C 0.35802(14) 0.0685(3) -0.11284(6) 0.0369(8) Uani 1 1 d . . . . .
C16C C 0.30243(13) 0.0532(3) -0.12522(6) 0.0474(9) Uani 1 1 d . . . . .
H16C H 0.2757 0.0140 -0.1145 0.057 Uiso 1 1 calc R U . . .
C17C C 0.28490(12) 0.0938(3) -0.15286(5) 0.0490(9) Uani 1 1 d . U . . .
H17C H 0.2470 0.0817 -0.1607 0.059 Uiso 1 1 calc R U . . .
C18C C 0.32401(15) 0.1525(3) -0.16886(6) 0.0446(9) Uani 1 1 d . U . . .
C19C C 0.37995(13) 0.1677(3) -0.15721(6) 0.0482(9) Uani 1 1 d . . . . .
H19C H 0.4067 0.2056 -0.1681 0.058 Uiso 1 1 calc R U . . .
C20C C 0.39652(12) 0.1272(3) -0.12944(6) 0.0487(9) Uani 1 1 d . . . . .
H20C H 0.4344 0.1395 -0.1216 0.058 Uiso 1 1 calc R U . . .
O1D O 0.47101(8) 0.38902(17) 0.20180(3) 0.0676(6) Uani 1 1 d . . . . .
H1DO H 0.5038 0.3601 0.2059 0.101 Uiso 1 1 calc R U . . .
O2D O 0.32205(7) 0.27473(17) 0.03383(3) 0.0500(6) Uani 1 1 d . . . . .
O3D O 0.27389(8) 0.37647(18) -0.03037(4) 0.0507(6) Uani 1 1 d . . . . .
O4D O 0.30438(8) 0.62171(18) -0.19675(4) 0.0728(7) Uani 1 1 d . . . . .
H4DO H 0.3131 0.5517 -0.2052 0.087 Uiso 1 1 calc R U . . .
N1D N 0.42600(9) 0.4997(2) 0.03535(4) 0.0400(7) Uani 1 1 d . . . . .
H1DN H 0.4504 0.5576 0.0299 0.048 Uiso 1 1 calc R U . . .
N2D N 0.37720(8) 0.5996(2) -0.02895(4) 0.0374(6) Uani 1 1 d . . . . .
H2DN H 0.4050 0.6544 -0.0230 0.045 Uiso 1 1 calc R U . . .
C1D C 0.49874(13) 0.5170(3) 0.13162(6) 0.0444(9) Uani 1 1 d . . . . .
H1D H 0.5295 0.5471 0.1225 0.053 Uiso 1 1 calc R U . . .
C2D C 0.50904(12) 0.4741(3) 0.15979(6) 0.0483(9) Uani 1 1 d . . . . .
H2D H 0.5461 0.4737 0.1692 0.058 Uiso 1 1 calc R U . . .
C3D C 0.46382(14) 0.4322(3) 0.17365(6) 0.0444(9) Uani 1 1 d . . . . .
C4D C 0.40951(13) 0.4338(3) 0.15952(6) 0.0522(9) Uani 1 1 d . . . . .
H4D H 0.3786 0.4069 0.1689 0.063 Uiso 1 1 calc R U . . .
C5D C 0.40060(12) 0.4754(2) 0.13135(5) 0.0447(9) Uani 1 1 d . . . . .
H5D H 0.3635 0.4755 0.1219 0.054 Uiso 1 1 calc R U . . .
C6D C 0.44538(14) 0.5171(3) 0.11668(6) 0.0373(8) Uani 1 1 d . . . . .
C7D C 0.43465(11) 0.5650(2) 0.08585(5) 0.0480(9) Uani 1 1 d . . . . .
H7DA H 0.3978 0.6114 0.0829 0.058 Uiso 1 1 calc R U . . .
H7DB H 0.4638 0.6321 0.0823 0.058 Uiso 1 1 calc R U . . .
C8D C 0.43517(10) 0.4480(2) 0.06460(5) 0.0419(8) Uani 1 1 d . . . . .
H8DA H 0.4717 0.4002 0.0677 0.050 Uiso 1 1 calc R U . . .
H8DB H 0.4053 0.3819 0.0676 0.050 Uiso 1 1 calc R U . . .
C9D C 0.38275(13) 0.4627(3) 0.01697(6) 0.0306(8) Uani 1 1 d . . . . .
C10D C 0.33608(12) 0.3609(3) 0.01672(6) 0.0359(8) Uani 1 1 d . . . . .
C11D C 0.31460(12) 0.4067(3) -0.01251(6) 0.0350(8) Uani 1 1 d . . . . .
C12D C 0.36184(12) 0.5058(3) -0.01114(6) 0.0321(8) Uani 1 1 d . . . . .
C13D C 0.34991(10) 0.6162(2) -0.05814(5) 0.0394(8) Uani 1 1 d . . . . .
H13G H 0.3408 0.7134 -0.0616 0.047 Uiso 1 1 calc R U . . .
H13H H 0.3143 0.5642 -0.0605 0.047 Uiso 1 1 calc R U . . .
C14D C 0.38793(11) 0.5666(3) -0.07962(5) 0.0537(9) Uani 1 1 d . . . . .
H14G H 0.4237 0.6179 -0.0769 0.064 Uiso 1 1 calc R U . . .
H14H H 0.3969 0.4694 -0.0760 0.064 Uiso 1 1 calc R U . . .
C15D C 0.36217(12) 0.5823(3) -0.11013(6) 0.0419(8) Uani 1 1 d . . . . .
C16D C 0.37224(12) 0.7005(3) -0.12536(6) 0.0511(9) Uani 1 1 d . . . . .
H16D H 0.3930 0.7729 -0.1161 0.061 Uiso 1 1 calc R U . . .
C17D C 0.35235(12) 0.7142(3) -0.15390(7) 0.0517(9) Uani 1 1 d . . . . .
H17D H 0.3594 0.7950 -0.1637 0.062 Uiso 1 1 calc R U . . .
C18D C 0.32212(13) 0.6077(3) -0.16764(6) 0.0427(9) Uani 1 1 d . U . . .
C19D C 0.30940(12) 0.4914(3) -0.15285(6) 0.0542(9) Uani 1 1 d . U . . .
H19D H 0.2872 0.4210 -0.1620 0.065 Uiso 1 1 calc R U . . .
C20D C 0.32971(13) 0.4795(3) -0.12440(6) 0.0485(9) Uani 1 1 d . . . . .
H20D H 0.3213 0.3999 -0.1145 0.058 Uiso 1 1 calc R U . . .
O1E O 0.11034(8) 0.15544(18) 0.19805(3) 0.0675(7) Uani 1 1 d . . . . .
H1EO H 0.1346 0.2153 0.2025 0.081 Uiso 1 1 calc R U . . .
O2E O 0.13414(8) 0.40516(19) 0.03165(4) 0.0539(6) Uani 1 1 d . U . . .
O3E O 0.08372(8) 0.50917(17) -0.03195(3) 0.0520(6) Uani 1 1 d . U . . .
O4E O -0.09882(8) 0.36745(17) -0.19619(3) 0.0682(7) Uani 1 1 d . . . . .
H4EO H -0.1304 0.3327 -0.2009 0.102 Uiso 1 1 calc R U . . .
N1E N 0.02496(9) 0.1973(2) 0.03292(4) 0.0428(7) Uani 1 1 d . . . . .
H1EN H -0.0040 0.1455 0.0272 0.051 Uiso 1 1 calc R U . . .
N2E N -0.02591(9) 0.3028(2) -0.03018(4) 0.0407(7) Uani 1 1 d . . . . .
H2EN H -0.0516 0.2519 -0.0237 0.049 Uiso 1 1 calc R U . . .
C1E C 0.03046(11) 0.0874(3) 0.12878(6) 0.0398(8) Uani 1 1 d . . . . .
H1E H 0.0088 0.0155 0.1198 0.048 Uiso 1 1 calc R U . . .
C2E C 0.05489(12) 0.0701(3) 0.15679(6) 0.0476(9) Uani 1 1 d . . . . .
H2E H 0.0502 -0.0129 0.1664 0.057 Uiso 1 1 calc R U . . .
C3E C 0.08634(13) 0.1769(4) 0.17041(6) 0.0434(9) Uani 1 1 d . . . . .
C4E C 0.09247(12) 0.2972(3) 0.15592(6) 0.0480(9) Uani 1 1 d . . . . .
H4E H 0.1132 0.3698 0.1652 0.058 Uiso 1 1 calc R U . . .
C5E C 0.06900(12) 0.3142(3) 0.12818(6) 0.0456(9) Uani 1 1 d . . . . .
H5E H 0.0742 0.3975 0.1188 0.055 Uiso 1 1 calc R U . . .
C6E C 0.03727(12) 0.2082(3) 0.11366(6) 0.0355(8) Uani 1 1 d . . . . .
C7E C 0.01141(11) 0.2230(3) 0.08326(5) 0.0495(9) Uani 1 1 d . . . . .
H7EA H 0.0001 0.3189 0.0798 0.059 Uiso 1 1 calc R U . . .
H7EB H -0.0229 0.1663 0.0802 0.059 Uiso 1 1 calc R U . . .
C8E C 0.05190(10) 0.1807(2) 0.06203(5) 0.0438(8) Uani 1 1 d . . . . .
H8EA H 0.0863 0.2372 0.0649 0.053 Uiso 1 1 calc R U . . .
H8EB H 0.0631 0.0845 0.0653 0.053 Uiso 1 1 calc R U . . .
C9E C 0.04210(12) 0.2862(3) 0.01486(5) 0.0322(8) Uani 1 1 d . . . . .
C10E C 0.09176(12) 0.3790(3) 0.01480(6) 0.0363(8) Uani 1 1 d . U . . .
C11E C 0.06880(12) 0.4263(3) -0.01431(5) 0.0362(8) Uani 1 1 d . U . . .
C12E C 0.02017(12) 0.3321(3) -0.01297(6) 0.0318(8) Uani 1 1 d . . . . .
C13E C -0.03633(11) 0.3507(2) -0.05941(5) 0.0416(8) Uani 1 1 d . . . . .
H13I H -0.0131 0.4324 -0.0616 0.050 Uiso 1 1 calc R U . . .
H13J H -0.0763 0.3775 -0.0635 0.050 Uiso 1 1 calc R U . . .
C14E C -0.02295(11) 0.2433(3) -0.08043(5) 0.0569(9) Uani 1 1 d . . . . .
H14I H -0.0406 0.1564 -0.0758 0.068 Uiso 1 1 calc R U . . .
H14J H 0.0182 0.2289 -0.0784 0.068 Uiso 1 1 calc R U . . .
C15E C -0.04276(13) 0.2783(3) -0.11103(6) 0.0425(8) Uani 1 1 d . U . . .
C16E C -0.09938(13) 0.2648(3) -0.12168(6) 0.0478(9) Uani 1 1 d . U . . .
H16E H -0.1254 0.2347 -0.1095 0.057 Uiso 1 1 calc R U . . .
C17E C -0.11900(12) 0.2941(3) -0.14963(6) 0.0474(9) Uani 1 1 d . . . . .
H17E H -0.1578 0.2848 -0.1562 0.057 Uiso 1 1 calc R U . . .
C18E C -0.08118(14) 0.3372(3) -0.16795(6) 0.0435(9) Uani 1 1 d . . . . .
C19E C -0.02472(14) 0.3536(3) -0.15773(6) 0.0528(10) Uani 1 1 d . . . . .
H19E H 0.0011 0.3845 -0.1699 0.063 Uiso 1 1 calc R U . . .
C20E C -0.00588(12) 0.3247(3) -0.12971(6) 0.0485(9) Uani 1 1 d . . . . .
H20E H 0.0327 0.3367 -0.1231 0.058 Uiso 1 1 calc R U . . .
S1A S 0.39362(4) 0.08474(9) 0.25499(2) 0.0848(3) Uani 1 1 d . . . . .
O5A O 0.35270(8) 0.09546(18) 0.27754(3) 0.0756(7) Uani 1 1 d . . . . .
C21A C 0.45181(12) 0.1906(3) 0.26751(5) 0.0981(12) Uani 1 1 d . . . . .
H21A H 0.4783 0.1944 0.2534 0.147 Uiso 1 1 calc R U . . .
H21B H 0.4708 0.1529 0.2850 0.147 Uiso 1 1 calc R U . . .
H21C H 0.4383 0.2825 0.2709 0.147 Uiso 1 1 calc R U . . .
C22A C 0.36646(12) 0.1914(3) 0.22639(5) 0.0985(12) Uani 1 1 d . . . . .
H22A H 0.3942 0.1991 0.2130 0.148 Uiso 1 1 calc R U . . .
H22B H 0.3585 0.2819 0.2335 0.148 Uiso 1 1 calc R U . . .
H22C H 0.3318 0.1517 0.2170 0.148 Uiso 1 1 calc R U . . .
S1B S 0.38342(4) 0.72721(8) 0.26087(2) 0.0608(3) Uani 1 1 d . . . . .
O5B O 0.44064(8) 0.71697(18) 0.27942(3) 0.0730(6) Uani 1 1 d . . . . .
C21B C 0.39727(12) 0.6910(3) 0.22607(5) 0.1113(14) Uani 1 1 d . . . . .
H21D H 0.3617 0.6827 0.2139 0.167 Uiso 1 1 calc R U . . .
H21E H 0.4182 0.6054 0.2259 0.167 Uiso 1 1 calc R U . . .
H21F H 0.4196 0.7648 0.2193 0.167 Uiso 1 1 calc R U . . .
C22B C 0.34554(11) 0.5746(2) 0.26827(5) 0.0880(11) Uani 1 1 d . . . . .
H22D H 0.3688 0.4947 0.2656 0.132 Uiso 1 1 calc R U . . .
H22E H 0.3106 0.5693 0.2555 0.132 Uiso 1 1 calc R U . . .
H22F H 0.3367 0.5773 0.2877 0.132 Uiso 1 1 calc R U . . .
S2C S 0.22525(3) 0.30670(8) 0.24688(2) 0.0576(3) Uani 1 1 d . . . . .
O5C O 0.20426(8) 0.31853(17) 0.21537(3) 0.0682(6) Uani 1 1 d . . . . .
C21C C 0.20375(12) 0.1402(2) 0.25798(5) 0.0910(12) Uani 1 1 d . . . . .
H21G H 0.1629 0.1316 0.2540 0.136 Uiso 1 1 calc R U . . .
H21H H 0.2150 0.1294 0.2782 0.136 Uiso 1 1 calc R U . . .
H21I H 0.2218 0.0697 0.2477 0.136 Uiso 1 1 calc R U . . .
C22C C 0.17841(13) 0.4091(3) 0.26431(6) 0.1169(14) Uani 1 1 d . . . . .
H22G H 0.1866 0.5054 0.2615 0.175 Uiso 1 1 calc R U . . .
H22H H 0.1834 0.3883 0.2844 0.175 Uiso 1 1 calc R U . . .
H22I H 0.1396 0.3896 0.2566 0.175 Uiso 1 1 calc R U . . .
S1D S 0.00972(4) 1.01253(8) 0.24438(2) 0.0730(3) Uani 1 1 d . . . . .
O5D O -0.03791(8) 0.99549(18) 0.22037(4) 0.0701(6) Uani 1 1 d . . . . .
C21D C -0.01187(13) 0.9206(3) 0.27390(5) 0.1016(13) Uani 1 1 d . . . . .
H21J H -0.0200 0.8259 0.2685 0.152 Uiso 1 1 calc R U . . .
H21K H -0.0457 0.9629 0.2797 0.152 Uiso 1 1 calc R U . . .
H21L H 0.0184 0.9231 0.2895 0.152 Uiso 1 1 calc R U . . .
C22D C 0.06421(11) 0.8971(3) 0.23687(5) 0.0919(11) Uani 1 1 d . . . . .
H22J H 0.0483 0.8060 0.2334 0.138 Uiso 1 1 calc R U . . .
H22K H 0.0935 0.8938 0.2529 0.138 Uiso 1 1 calc R U . . .
H22L H 0.0805 0.9285 0.2202 0.138 Uiso 1 1 calc R U . . .
O1W O 0.20952(12) 0.7760(3) 0.26927(5) 0.1001(10) Uani 1 1 d . . . . .
H1W H 0.2291(16) 0.824(3) 0.2793(7) 0.120 Uiso 1 1 d . U . . .
H1WA H 0.1798(12) 0.745(3) 0.2803(6) 0.120 Uiso 1 1 d . U . . .
O2W O 0.20944(9) 0.7430(2) 0.21358(4) 0.0655(7) Uani 1 1 d . . . . .
H2W H 0.2064(11) 0.762(2) 0.2330(5) 0.079 Uiso 1 1 d . U . . .
H2WA H 0.2352(11) 0.666(2) 0.2114(5) 0.079 Uiso 1 1 d . 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
O1A C3A 1.378(3) . ?
O1A H1AO 0.8200 . ?
O2A C10A 1.229(3) . ?
O3A C11A 1.239(2) . ?
O4A C18A 1.385(3) . ?
O4A H4AO 0.8200 . ?
N1A C9A 1.314(2) . ?
N1A C8A 1.446(2) . ?
N1A H1AA 0.8600 . ?
N2A C12A 1.309(3) . ?
N2A C13A 1.453(2) . ?
N2A H2AN 0.8600 . ?
C1A C2A 1.367(3) . ?
C1A C6A 1.386(3) . ?
C1A H1A 0.9300 . ?
C2A C3A 1.370(3) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.378(3) . ?
C4A C5A 1.371(3) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.374(3) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.500(3) . ?
C7A C8A 1.511(2) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C9A C12A 1.409(3) . ?
C9A C10A 1.465(3) . ?
C10A C11A 1.482(3) . ?
C11A C12A 1.455(3) . ?
C13A C14A 1.506(2) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.503(3) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A C16A 1.374(3) . ?
C15A C20A 1.375(3) . ?
C16A C17A 1.371(3) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.357(3) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.377(3) . ?
C19A C20A 1.381(3) . ?
C19A H19A 0.9300 . ?
C20A H20A 0.9300 . ?
O1B C3B 1.385(3) . ?
O1B H1BO 0.8200 . ?
O2B C10B 1.234(2) . ?
O3B C11B 1.226(3) . ?
O4B C18B 1.392(3) . ?
O4B H4BO 0.8200 . ?
N1B C9B 1.305(3) . ?
N1B C8B 1.462(2) . ?
N1B H1BN 0.8600 . ?
N2B C12B 1.307(2) . ?
N2B C13B 1.455(2) . ?
N2B H2BN 0.8600 . ?
C1B C6B 1.381(3) . ?
C1B C2B 1.390(3) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.372(3) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.356(3) . ?
C4B C5B 1.369(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.374(3) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.509(3) . ?
C7B C8B 1.508(3) . ?
C7B H7BA 0.9700 . ?
C7B H7BB 0.9700 . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C9B C12B 1.418(3) . ?
C9B C10B 1.452(3) . ?
C10B C11B 1.489(3) . ?
C11B C12B 1.455(3) . ?
C13B C14B 1.499(3) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.503(3) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B C16B 1.376(3) . ?
C15B C20B 1.384(3) . ?
C16B C17B 1.382(3) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.355(3) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.371(3) . ?
C19B C20B 1.377(3) . ?
C19B H19B 0.9300 . ?
C20B H20B 0.9300 . ?
O1C C3C 1.377(3) . ?
O1C H1CO 0.8200 . ?
O2C C10C 1.236(3) . ?
O3C C11C 1.236(2) . ?
O4C C18C 1.376(3) . ?
O4C H4CO 0.8200 . ?
N1C C9C 1.311(2) . ?
N1C C8C 1.455(2) . ?
N1C H1CN 0.8600 . ?
N2C C12C 1.307(3) . ?
N2C C13C 1.447(2) . ?
N2C H2CN 0.8600 . ?
C1C C6C 1.379(3) . ?
C1C C2C 1.379(3) . ?
C1C H1C 0.9300 . ?
C2C C3C 1.369(3) . ?
C2C H2C 0.9300 . ?
C3C C4C 1.363(3) . ?
C4C C5C 1.376(3) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.382(3) . ?
C5C H5C 0.9300 . ?
C6C C7C 1.504(3) . ?
C7C C8C 1.502(2) . ?
C7C H7CA 0.9700 . ?
C7C H7CB 0.9700 . ?
C8C H8CA 0.9700 . ?
C8C H8CB 0.9700 . ?
C9C C12C 1.415(3) . ?
C9C C10C 1.454(3) . ?
C10C C11C 1.475(3) . ?
C11C C12C 1.458(3) . ?
C13C C14C 1.506(3) . ?
C13C H13E 0.9700 . ?
C13C H13F 0.9700 . ?
C14C C15C 1.502(3) . ?
C14C H14E 0.9700 . ?
C14C H14F 0.9700 . ?
C15C C16C 1.373(3) . ?
C15C C20C 1.383(3) . ?
C16C C17C 1.373(3) . ?
C16C H16C 0.9300 . ?
C17C C18C 1.375(3) . ?
C17C H17C 0.9300 . ?
C18C C19C 1.370(3) . ?
C19C C20C 1.375(3) . ?
C19C H19C 0.9300 . ?
C20C H20C 0.9300 . ?
O1D C3D 1.379(3) . ?
O1D H1DO 0.8200 . ?
O2D C10D 1.228(2) . ?
O3D C11D 1.231(3) . ?
O4D C18D 1.390(3) . ?
O4D H4DO 0.8200 . ?
N1D C9D 1.303(3) . ?
N1D C8D 1.455(2) . ?
N1D H1DN 0.8600 . ?
N2D C12D 1.311(2) . ?
N2D C13D 1.454(2) . ?
N2D H2DN 0.8600 . ?
C1D C6D 1.363(3) . ?
C1D C2D 1.382(3) . ?
C1D H1D 0.9300 . ?
C2D C3D 1.370(3) . ?
C2D H2D 0.9300 . ?
C3D C4D 1.367(3) . ?
C4D C5D 1.376(3) . ?
C4D H4D 0.9300 . ?
C5D C6D 1.383(3) . ?
C5D H5D 0.9300 . ?
C6D C7D 1.514(3) . ?
C7D C8D 1.507(3) . ?
C7D H7DA 0.9700 . ?
C7D H7DB 0.9700 . ?
C8D H8DA 0.9700 . ?
C8D H8DB 0.9700 . ?
C9D C12D 1.418(3) . ?
C9D C10D 1.469(3) . ?
C10D C11D 1.475(3) . ?
C11D C12D 1.459(3) . ?
C13D C14D 1.503(2) . ?
C13D H13G 0.9700 . ?
C13D H13H 0.9700 . ?
C14D C15D 1.498(3) . ?
C14D H14G 0.9700 . ?
C14D H14H 0.9700 . ?
C15D C20D 1.376(3) . ?
C15D C16D 1.380(3) . ?
C16D C17D 1.375(3) . ?
C16D H16D 0.9300 . ?
C17D C18D 1.366(3) . ?
C17D H17D 0.9300 . ?
C18D C19D 1.370(3) . ?
C19D C20D 1.371(3) . ?
C19D H19D 0.9300 . ?
C20D H20D 0.9300 . ?
O1E C3E 1.370(3) . ?
O1E H1EO 0.8200 . ?
O2E C10E 1.223(3) . ?
O3E C11E 1.232(2) . ?
O4E C18E 1.375(3) . ?
O4E H4EO 0.8200 . ?
N1E C9E 1.303(2) . ?
N1E C8E 1.448(2) . ?
N1E H1EN 0.8600 . ?
N2E C12E 1.304(3) . ?
N2E C13E 1.444(2) . ?
N2E H2EN 0.8600 . ?
C1E C2E 1.384(3) . ?
C1E C6E 1.383(3) . ?
C1E H1E 0.9300 . ?
C2E C3E 1.379(3) . ?
C2E H2E 0.9300 . ?
C3E C4E 1.361(3) . ?
C4E C5E 1.365(3) . ?
C4E H4E 0.9300 . ?
C5E C6E 1.394(3) . ?
C5E H5E 0.9300 . ?
C6E C7E 1.493(3) . ?
C7E C8E 1.513(2) . ?
C7E H7EA 0.9700 . ?
C7E H7EB 0.9700 . ?
C8E H8EA 0.9700 . ?
C8E H8EB 0.9700 . ?
C9E C12E 1.419(3) . ?
C9E C10E 1.470(3) . ?
C10E C11E 1.482(3) . ?
C11E C12E 1.466(3) . ?
C13E C14E 1.490(3) . ?
C13E H13I 0.9700 . ?
C13E H13J 0.9700 . ?
C14E C15E 1.498(3) . ?
C14E H14I 0.9700 . ?
C14E H14J 0.9700 . ?
C15E C16E 1.371(3) . ?
C15E C20E 1.379(3) . ?
C16E C17E 1.370(3) . ?
C16E H16E 0.9300 . ?
C17E C18E 1.373(3) . ?
C17E H17E 0.9300 . ?
C18E C19E 1.365(3) . ?
C19E C20E 1.368(3) . ?
C19E H19E 0.9300 . ?
C20E H20E 0.9300 . ?
S1A O5A 1.5159(16) . ?
S1A C21A 1.750(3) . ?
S1A C22A 1.752(2) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C22A H22A 0.9600 . ?
C22A H22B 0.9600 . ?
C22A H22C 0.9600 . ?
S1B O5B 1.5169(19) . ?
S1B C21B 1.741(2) . ?
S1B C22B 1.774(2) . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
C22B H22D 0.9600 . ?
C22B H22E 0.9600 . ?
C22B H22F 0.9600 . ?
S2C O5C 1.5100(16) . ?
S2C C22C 1.751(2) . ?
S2C C21C 1.778(2) . ?
C21C H21G 0.9600 . ?
C21C H21H 0.9600 . ?
C21C H21I 0.9600 . ?
C22C H22G 0.9600 . ?
C22C H22H 0.9600 . ?
C22C H22I 0.9600 . ?
S1D O5D 1.5020(19) . ?
S1D C22D 1.762(3) . ?
S1D C21D 1.771(2) . ?
C21D H21J 0.9600 . ?
C21D H21K 0.9600 . ?
C21D H21L 0.9600 . ?
C22D H22J 0.9600 . ?
C22D H22K 0.9600 . ?
C22D H22L 0.9600 . ?
O1W H1W 0.77(3) . ?
O1W H1WA 0.96(3) . ?
O2W H2W 0.94(2) . ?
O2W H2WA 0.97(2) . ?

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
C3A O1A H1AO 109.5 . . ?
C18A O4A H4AO 109.5 . . ?
C9A N1A C8A 123.9(2) . . ?
C9A N1A H1AA 118.1 . . ?
C8A N1A H1AA 118.1 . . ?
C12A N2A C13A 123.4(2) . . ?
C12A N2A H2AN 118.3 . . ?
C13A N2A H2AN 118.3 . . ?
C2A C1A C6A 121.1(3) . . ?
C2A C1A H1A 119.4 . . ?
C6A C1A H1A 119.4 . . ?
C1A C2A C3A 120.8(3) . . ?
C1A C2A H2A 119.6 . . ?
C3A C2A H2A 119.6 . . ?
C2A C3A O1A 122.6(3) . . ?
C2A C3A C4A 119.0(3) . . ?
O1A C3A C4A 118.4(3) . . ?
C5A C4A C3A 119.6(3) . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A H4A 120.2 . . ?
C4A C5A C6A 122.3(3) . . ?
C4A C5A H5A 118.9 . . ?
C6A C5A H5A 118.9 . . ?
C5A C6A C1A 117.1(3) . . ?
C5A C6A C7A 121.7(3) . . ?
C1A C6A C7A 121.2(3) . . ?
C6A C7A C8A 113.5(2) . . ?
C6A C7A H7AA 108.9 . . ?
C8A C7A H7AA 108.9 . . ?
C6A C7A H7AB 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
H7AA C7A H7AB 107.7 . . ?
N1A C8A C7A 112.8(2) . . ?
N1A C8A H8AA 109.0 . . ?
C7A C8A H8AA 109.0 . . ?
N1A C8A H8AB 109.0 . . ?
C7A C8A H8AB 109.0 . . ?
H8AA C8A H8AB 107.8 . . ?
N1A C9A C12A 133.9(3) . . ?
N1A C9A C10A 134.4(3) . . ?
C12A C9A C10A 91.7(2) . . ?
O2A C10A C9A 136.0(3) . . ?
O2A C10A C11A 136.0(3) . . ?
C9A C10A C11A 87.9(2) . . ?
O3A C11A C12A 135.8(3) . . ?
O3A C11A C10A 135.1(3) . . ?
C12A C11A C10A 89.2(2) . . ?
N2A C12A C9A 134.6(3) . . ?
N2A C12A C11A 134.2(3) . . ?
C9A C12A C11A 91.2(2) . . ?
N2A C13A C14A 111.24(19) . . ?
N2A C13A H13A 109.4 . . ?
C14A C13A H13A 109.4 . . ?
N2A C13A H13B 109.4 . . ?
C14A C13A H13B 109.4 . . ?
H13A C13A H13B 108.0 . . ?
C15A C14A C13A 113.0(2) . . ?
C15A C14A H14A 109.0 . . ?
C13A C14A H14A 109.0 . . ?
C15A C14A H14B 109.0 . . ?
C13A C14A H14B 109.0 . . ?
H14A C14A H14B 107.8 . . ?
C16A C15A C20A 116.7(3) . . ?
C16A C15A C14A 122.6(3) . . ?
C20A C15A C14A 120.6(3) . . ?
C17A C16A C15A 122.0(3) . . ?
C17A C16A H16A 119.0 . . ?
C15A C16A H16A 119.0 . . ?
C18A C17A C16A 120.6(3) . . ?
C18A C17A H17A 119.7 . . ?
C16A C17A H17A 119.7 . . ?
C17A C18A C19A 119.1(3) . . ?
C17A C18A O4A 123.3(3) . . ?
C19A C18A O4A 117.7(3) . . ?
C18A C19A C20A 119.6(3) . . ?
C18A C19A H19A 120.2 . . ?
C20A C19A H19A 120.2 . . ?
C15A C20A C19A 121.9(3) . . ?
C15A C20A H20A 119.0 . . ?
C19A C20A H20A 119.0 . . ?
C3B O1B H1BO 109.5 . . ?
C18B O4B H4BO 109.5 . . ?
C9B N1B C8B 123.6(2) . . ?
C9B N1B H1BN 118.2 . . ?
C8B N1B H1BN 118.2 . . ?
C12B N2B C13B 124.3(2) . . ?
C12B N2B H2BN 117.8 . . ?
C13B N2B H2BN 117.8 . . ?
C6B C1B C2B 121.7(3) . . ?
C6B C1B H1B 119.2 . . ?
C2B C1B H1B 119.2 . . ?
C3B C2B C1B 118.5(3) . . ?
C3B C2B H2B 120.7 . . ?
C1B C2B H2B 120.7 . . ?
C4B C3B C2B 120.5(3) . . ?
C4B C3B O1B 117.4(3) . . ?
C2B C3B O1B 122.0(3) . . ?
C3B C4B C5B 120.3(3) . . ?
C3B C4B H4B 119.8 . . ?
C5B C4B H4B 119.8 . . ?
C4B C5B C6B 121.5(3) . . ?
C4B C5B H5B 119.2 . . ?
C6B C5B H5B 119.2 . . ?
C5B C6B C1B 117.4(3) . . ?
C5B C6B C7B 123.0(3) . . ?
C1B C6B C7B 119.6(3) . . ?
C8B C7B C6B 112.6(2) . . ?
C8B C7B H7BA 109.1 . . ?
C6B C7B H7BA 109.1 . . ?
C8B C7B H7BB 109.1 . . ?
C6B C7B H7BB 109.1 . . ?
H7BA C7B H7BB 107.8 . . ?
N1B C8B C7B 111.0(2) . . ?
N1B C8B H8BA 109.4 . . ?
C7B C8B H8BA 109.4 . . ?
N1B C8B H8BB 109.4 . . ?
C7B C8B H8BB 109.4 . . ?
H8BA C8B H8BB 108.0 . . ?
N1B C9B C12B 133.5(3) . . ?
N1B C9B C10B 135.4(3) . . ?
C12B C9B C10B 91.1(2) . . ?
O2B C10B C9B 135.5(3) . . ?
O2B C10B C11B 135.5(3) . . ?
C9B C10B C11B 89.0(2) . . ?
O3B C11B C12B 135.9(3) . . ?
O3B C11B C10B 135.8(3) . . ?
C12B C11B C10B 88.2(2) . . ?
N2B C12B C9B 133.9(3) . . ?
N2B C12B C11B 134.4(3) . . ?
C9B C12B C11B 91.7(2) . . ?
N2B C13B C14B 111.3(2) . . ?
N2B C13B H13C 109.4 . . ?
C14B C13B H13C 109.4 . . ?
N2B C13B H13D 109.4 . . ?
C14B C13B H13D 109.4 . . ?
H13C C13B H13D 108.0 . . ?
C13B C14B C15B 114.4(2) . . ?
C13B C14B H14C 108.7 . . ?
C15B C14B H14C 108.7 . . ?
C13B C14B H14D 108.7 . . ?
C15B C14B H14D 108.7 . . ?
H14C C14B H14D 107.6 . . ?
C16B C15B C20B 117.9(3) . . ?
C16B C15B C14B 122.0(3) . . ?
C20B C15B C14B 120.0(3) . . ?
C15B C16B C17B 120.5(3) . . ?
C15B C16B H16B 119.7 . . ?
C17B C16B H16B 119.7 . . ?
C18B C17B C16B 120.1(3) . . ?
C18B C17B H17B 119.9 . . ?
C16B C17B H17B 119.9 . . ?
C17B C18B C19B 120.9(3) . . ?
C17B C18B O4B 118.8(3) . . ?
C19B C18B O4B 120.2(3) . . ?
C18B C19B C20B 118.6(3) . . ?
C18B C19B H19B 120.7 . . ?
C20B C19B H19B 120.7 . . ?
C19B C20B C15B 121.8(3) . . ?
C19B C20B H20B 119.1 . . ?
C15B C20B H20B 119.1 . . ?
C3C O1C H1CO 109.5 . . ?
C18C O4C H4CO 109.5 . . ?
C9C N1C C8C 123.1(2) . . ?
C9C N1C H1CN 118.4 . . ?
C8C N1C H1CN 118.4 . . ?
C12C N2C C13C 124.0(2) . . ?
C12C N2C H2CN 118.0 . . ?
C13C N2C H2CN 118.0 . . ?
C6C C1C C2C 121.6(3) . . ?
C6C C1C H1C 119.2 . . ?
C2C C1C H1C 119.2 . . ?
C3C C2C C1C 120.0(3) . . ?
C3C C2C H2C 120.0 . . ?
C1C C2C H2C 120.0 . . ?
C4C C3C C2C 119.4(3) . . ?
C4C C3C O1C 118.3(3) . . ?
C2C C3C O1C 122.3(3) . . ?
C3C C4C C5C 120.4(3) . . ?
C3C C4C H4C 119.8 . . ?
C5C C4C H4C 119.8 . . ?
C4C C5C C6C 121.5(3) . . ?
C4C C5C H5C 119.3 . . ?
C6C C5C H5C 119.3 . . ?
C1C C6C C5C 117.1(3) . . ?
C1C C6C C7C 121.1(3) . . ?
C5C C6C C7C 121.8(3) . . ?
C8C C7C C6C 113.6(2) . . ?
C8C C7C H7CA 108.8 . . ?
C6C C7C H7CA 108.8 . . ?
C8C C7C H7CB 108.8 . . ?
C6C C7C H7CB 108.8 . . ?
H7CA C7C H7CB 107.7 . . ?
N1C C8C C7C 112.1(2) . . ?
N1C C8C H8CA 109.2 . . ?
C7C C8C H8CA 109.2 . . ?
N1C C8C H8CB 109.2 . . ?
C7C C8C H8CB 109.2 . . ?
H8CA C8C H8CB 107.9 . . ?
N1C C9C C12C 133.7(3) . . ?
N1C C9C C10C 135.3(3) . . ?
C12C C9C C10C 91.0(2) . . ?
O2C C10C C9C 135.4(3) . . ?
O2C C10C C11C 135.4(3) . . ?
C9C C10C C11C 89.2(2) . . ?
O3C C11C C12C 135.4(3) . . ?
O3C C11C C10C 136.2(3) . . ?
C12C C11C C10C 88.5(2) . . ?
N2C C12C C9C 133.9(3) . . ?
N2C C12C C11C 134.7(3) . . ?
C9C C12C C11C 91.4(2) . . ?
N2C C13C C14C 111.8(2) . . ?
N2C C13C H13E 109.3 . . ?
C14C C13C H13E 109.3 . . ?
N2C C13C H13F 109.3 . . ?
C14C C13C H13F 109.3 . . ?
H13E C13C H13F 107.9 . . ?
C15C C14C C13C 113.2(2) . . ?
C15C C14C H14E 108.9 . . ?
C13C C14C H14E 108.9 . . ?
C15C C14C H14F 108.9 . . ?
C13C C14C H14F 108.9 . . ?
H14E C14C H14F 107.8 . . ?
C16C C15C C20C 117.2(3) . . ?
C16C C15C C14C 120.7(3) . . ?
C20C C15C C14C 122.1(3) . . ?
C17C C16C C15C 122.3(3) . . ?
C17C C16C H16C 118.8 . . ?
C15C C16C H16C 118.8 . . ?
C16C C17C C18C 119.3(3) . . ?
C16C C17C H17C 120.3 . . ?
C18C C17C H17C 120.3 . . ?
C19C C18C C17C 119.7(3) . . ?
C19C C18C O4C 123.8(3) . . ?
C17C C18C O4C 116.4(3) . . ?
C18C C19C C20C 120.0(3) . . ?
C18C C19C H19C 120.0 . . ?
C20C C19C H19C 120.0 . . ?
C19C C20C C15C 121.4(3) . . ?
C19C C20C H20C 119.3 . . ?
C15C C20C H20C 119.3 . . ?
C3D O1D H1DO 109.5 . . ?
C18D O4D H4DO 109.5 . . ?
C9D N1D C8D 123.4(2) . . ?
C9D N1D H1DN 118.3 . . ?
C8D N1D H1DN 118.3 . . ?
C12D N2D C13D 123.7(2) . . ?
C12D N2D H2DN 118.1 . . ?
C13D N2D H2DN 118.1 . . ?
C6D C1D C2D 122.8(3) . . ?
C6D C1D H1D 118.6 . . ?
C2D C1D H1D 118.6 . . ?
C3D C2D C1D 119.1(3) . . ?
C3D C2D H2D 120.5 . . ?
C1D C2D H2D 120.5 . . ?
C4D C3D C2D 119.8(3) . . ?
C4D C3D O1D 118.1(3) . . ?
C2D C3D O1D 122.1(3) . . ?
C3D C4D C5D 119.9(3) . . ?
C3D C4D H4D 120.0 . . ?
C5D C4D H4D 120.0 . . ?
C4D C5D C6D 121.7(3) . . ?
C4D C5D H5D 119.1 . . ?
C6D C5D H5D 119.1 . . ?
C1D C6D C5D 116.7(3) . . ?
C1D C6D C7D 122.2(3) . . ?
C5D C6D C7D 121.0(3) . . ?
C8D C7D C6D 113.2(2) . . ?
C8D C7D H7DA 108.9 . . ?
C6D C7D H7DA 108.9 . . ?
C8D C7D H7DB 108.9 . . ?
C6D C7D H7DB 108.9 . . ?
H7DA C7D H7DB 107.8 . . ?
N1D C8D C7D 111.1(2) . . ?
N1D C8D H8DA 109.4 . . ?
C7D C8D H8DA 109.4 . . ?
N1D C8D H8DB 109.4 . . ?
C7D C8D H8DB 109.4 . . ?
H8DA C8D H8DB 108.0 . . ?
N1D C9D C12D 134.1(3) . . ?
N1D C9D C10D 135.2(3) . . ?
C12D C9D C10D 90.7(2) . . ?
O2D C10D C9D 134.7(3) . . ?
O2D C10D C11D 136.4(3) . . ?
C9D C10D C11D 88.9(2) . . ?
O3D C11D C12D 135.2(3) . . ?
O3D C11D C10D 135.9(3) . . ?
C12D C11D C10D 88.8(2) . . ?
N2D C12D C9D 135.0(3) . . ?
N2D C12D C11D 133.5(3) . . ?
C9D C12D C11D 91.6(2) . . ?
N2D C13D C14D 111.6(2) . . ?
N2D C13D H13G 109.3 . . ?
C14D C13D H13G 109.3 . . ?
N2D C13D H13H 109.3 . . ?
C14D C13D H13H 109.3 . . ?
H13G C13D H13H 108.0 . . ?
C15D C14D C13D 114.0(2) . . ?
C15D C14D H14G 108.8 . . ?
C13D C14D H14G 108.8 . . ?
C15D C14D H14H 108.8 . . ?
C13D C14D H14H 108.8 . . ?
H14G C14D H14H 107.6 . . ?
C20D C15D C16D 117.4(3) . . ?
C20D C15D C14D 122.2(3) . . ?
C16D C15D C14D 120.4(3) . . ?
C17D C16D C15D 121.8(3) . . ?
C17D C16D H16D 119.1 . . ?
C15D C16D H16D 119.1 . . ?
C18D C17D C16D 119.2(3) . . ?
C18D C17D H17D 120.4 . . ?
C16D C17D H17D 120.4 . . ?
C17D C18D C19D 120.4(3) . . ?
C17D C18D O4D 118.2(3) . . ?
C19D C18D O4D 121.4(3) . . ?
C18D C19D C20D 119.5(3) . . ?
C18D C19D H19D 120.3 . . ?
C20D C19D H19D 120.3 . . ?
C19D C20D C15D 121.7(3) . . ?
C19D C20D H20D 119.2 . . ?
C15D C20D H20D 119.2 . . ?
C3E O1E H1EO 109.5 . . ?
C18E O4E H4EO 109.5 . . ?
C9E N1E C8E 123.7(2) . . ?
C9E N1E H1EN 118.1 . . ?
C8E N1E H1EN 118.1 . . ?
C12E N2E C13E 123.9(2) . . ?
C12E N2E H2EN 118.1 . . ?
C13E N2E H2EN 118.1 . . ?
C2E C1E C6E 122.0(3) . . ?
C2E C1E H1E 119.0 . . ?
C6E C1E H1E 119.0 . . ?
C3E C2E C1E 119.5(3) . . ?
C3E C2E H2E 120.3 . . ?
C1E C2E H2E 120.3 . . ?
C4E C3E O1E 123.2(3) . . ?
C4E C3E C2E 119.0(3) . . ?
O1E C3E C2E 117.8(3) . . ?
C3E C4E C5E 121.7(3) . . ?
C3E C4E H4E 119.1 . . ?
C5E C4E H4E 119.1 . . ?
C4E C5E C6E 120.9(3) . . ?
C4E C5E H5E 119.6 . . ?
C6E C5E H5E 119.6 . . ?
C1E C6E C5E 116.9(3) . . ?
C1E C6E C7E 120.9(3) . . ?
C5E C6E C7E 122.2(3) . . ?
C6E C7E C8E 112.9(2) . . ?
C6E C7E H7EA 109.0 . . ?
C8E C7E H7EA 109.0 . . ?
C6E C7E H7EB 109.0 . . ?
C8E C7E H7EB 109.0 . . ?
H7EA C7E H7EB 107.8 . . ?
N1E C8E C7E 110.8(2) . . ?
N1E C8E H8EA 109.5 . . ?
C7E C8E H8EA 109.5 . . ?
N1E C8E H8EB 109.5 . . ?
C7E C8E H8EB 109.5 . . ?
H8EA C8E H8EB 108.1 . . ?
N1E C9E C12E 134.4(3) . . ?
N1E C9E C10E 135.0(3) . . ?
C12E C9E C10E 90.6(2) . . ?
O2E C10E C9E 135.2(3) . . ?
O2E C10E C11E 135.6(3) . . ?
C9E C10E C11E 89.2(2) . . ?
O3E C11E C12E 135.6(3) . . ?
O3E C11E C10E 136.0(3) . . ?
C12E C11E C10E 88.3(2) . . ?
N2E C12E C9E 133.6(3) . . ?
N2E C12E C11E 134.5(3) . . ?
C9E C12E C11E 91.9(2) . . ?
N2E C13E C14E 112.6(2) . . ?
N2E C13E H13I 109.1 . . ?
C14E C13E H13I 109.1 . . ?
N2E C13E H13J 109.1 . . ?
C14E C13E H13J 109.1 . . ?
H13I C13E H13J 107.8 . . ?
C13E C14E C15E 114.5(2) . . ?
C13E C14E H14I 108.6 . . ?
C15E C14E H14I 108.6 . . ?
C13E C14E H14J 108.6 . . ?
C15E C14E H14J 108.6 . . ?
H14I C14E H14J 107.6 . . ?
C16E C15E C20E 116.9(3) . . ?
C16E C15E C14E 120.5(3) . . ?
C20E C15E C14E 122.5(3) . . ?
C17E C16E C15E 122.2(3) . . ?
C17E C16E H16E 118.9 . . ?
C15E C16E H16E 118.9 . . ?
C16E C17E C18E 119.7(3) . . ?
C16E C17E H17E 120.2 . . ?
C18E C17E H17E 120.2 . . ?
C19E C18E C17E 119.2(3) . . ?
C19E C18E O4E 119.0(3) . . ?
C17E C18E O4E 121.8(3) . . ?
C18E C19E C20E 120.4(3) . . ?
C18E C19E H19E 119.8 . . ?
C20E C19E H19E 119.8 . . ?
C19E C20E C15E 121.6(3) . . ?
C19E C20E H20E 119.2 . . ?
C15E C20E H20E 119.2 . . ?
O5A S1A C21A 105.03(12) . . ?
O5A S1A C22A 107.07(13) . . ?
C21A S1A C22A 96.65(13) . . ?
S1A C21A H21A 109.5 . . ?
S1A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
S1A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
S1A C22A H22A 109.5 . . ?
S1A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
S1A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
O5B S1B C21B 106.06(13) . . ?
O5B S1B C22B 105.32(12) . . ?
C21B S1B C22B 99.90(13) . . ?
S1B C21B H21D 109.5 . . ?
S1B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
S1B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
S1B C22B H22D 109.5 . . ?
S1B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
S1B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
O5C S2C C22C 105.45(13) . . ?
O5C S2C C21C 106.56(12) . . ?
C22C S2C C21C 98.90(13) . . ?
S2C C21C H21G 109.5 . . ?
S2C C21C H21H 109.5 . . ?
H21G C21C H21H 109.5 . . ?
S2C C21C H21I 109.5 . . ?
H21G C21C H21I 109.5 . . ?
H21H C21C H21I 109.5 . . ?
S2C C22C H22G 109.5 . . ?
S2C C22C H22H 109.5 . . ?
H22G C22C H22H 109.5 . . ?
S2C C22C H22I 109.5 . . ?
H22G C22C H22I 109.5 . . ?
H22H C22C H22I 109.5 . . ?
O5D S1D C22D 105.93(12) . . ?
O5D S1D C21D 106.15(14) . . ?
C22D S1D C21D 97.09(12) . . ?
S1D C21D H21J 109.5 . . ?
S1D C21D H21K 109.5 . . ?
H21J C21D H21K 109.5 . . ?
S1D C21D H21L 109.5 . . ?
H21J C21D H21L 109.5 . . ?
H21K C21D H21L 109.5 . . ?
S1D C22D H22J 109.5 . . ?
S1D C22D H22K 109.5 . . ?
H22J C22D H22K 109.5 . . ?
S1D C22D H22L 109.5 . . ?
H22J C22D H22L 109.5 . . ?
H22K C22D H22L 109.5 . . ?
H1W O1W H1WA 106(3) . . ?
H2W O2W H2WA 112(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A C3A 0.2(4) . . . . ?
C1A C2A C3A O1A 179.8(2) . . . . ?
C1A C2A C3A C4A -1.2(4) . . . . ?
C2A C3A C4A C5A 1.8(4) . . . . ?
O1A C3A C4A C5A -179.2(2) . . . . ?
C3A C4A C5A C6A -1.5(4) . . . . ?
C4A C5A C6A C1A 0.5(4) . . . . ?
C4A C5A C6A C7A -179.8(2) . . . . ?
C2A C1A C6A C5A 0.2(4) . . . . ?
C2A C1A C6A C7A -179.6(2) . . . . ?
C5A C6A C7A C8A -97.5(3) . . . . ?
C1A C6A C7A C8A 82.3(3) . . . . ?
C9A N1A C8A C7A 116.7(2) . . . . ?
C6A C7A C8A N1A -179.1(2) . . . . ?
C8A N1A C9A C12A -176.1(3) . . . . ?
C8A N1A C9A C10A 6.3(4) . . . . ?
N1A C9A C10A O2A -2.6(6) . . . . ?
C12A C9A C10A O2A 179.1(4) . . . . ?
N1A C9A C10A C11A 179.2(3) . . . . ?
C12A C9A C10A C11A 0.9(2) . . . . ?
O2A C10A C11A O3A 1.7(6) . . . . ?
C9A C10A C11A O3A 179.9(3) . . . . ?
O2A C10A C11A C12A -179.1(4) . . . . ?
C9A C10A C11A C12A -0.9(2) . . . . ?
C13A N2A C12A C9A -175.0(3) . . . . ?
C13A N2A C12A C11A 6.5(5) . . . . ?
N1A C9A C12A N2A 1.8(5) . . . . ?
C10A C9A C12A N2A -179.9(3) . . . . ?
N1A C9A C12A C11A -179.3(3) . . . . ?
C10A C9A C12A C11A -0.9(2) . . . . ?
O3A C11A C12A N2A -1.0(6) . . . . ?
C10A C11A C12A N2A 179.8(3) . . . . ?
O3A C11A C12A C9A -179.9(3) . . . . ?
C10A C11A C12A C9A 0.9(2) . . . . ?
C12A N2A C13A C14A 112.0(3) . . . . ?
N2A C13A C14A C15A 178.5(2) . . . . ?
C13A C14A C15A C16A 89.1(3) . . . . ?
C13A C14A C15A C20A -91.1(3) . . . . ?
C20A C15A C16A C17A 1.1(4) . . . . ?
C14A C15A C16A C17A -179.1(2) . . . . ?
C15A C16A C17A C18A 1.0(4) . . . . ?
C16A C17A C18A C19A -1.9(4) . . . . ?
C16A C17A C18A O4A 177.9(2) . . . . ?
C17A C18A C19A C20A 0.6(4) . . . . ?
O4A C18A C19A C20A -179.2(2) . . . . ?
C16A C15A C20A C19A -2.4(4) . . . . ?
C14A C15A C20A C19A 177.9(2) . . . . ?
C18A C19A C20A C15A 1.5(4) . . . . ?
C6B C1B C2B C3B -0.7(4) . . . . ?
C1B C2B C3B C4B 0.1(4) . . . . ?
C1B C2B C3B O1B -178.3(2) . . . . ?
C2B C3B C4B C5B 0.2(5) . . . . ?
O1B C3B C4B C5B 178.6(2) . . . . ?
C3B C4B C5B C6B 0.2(4) . . . . ?
C4B C5B C6B C1B -0.9(4) . . . . ?
C4B C5B C6B C7B 179.8(2) . . . . ?
C2B C1B C6B C5B 1.1(4) . . . . ?
C2B C1B C6B C7B -179.5(2) . . . . ?
C5B C6B C7B C8B -89.1(3) . . . . ?
C1B C6B C7B C8B 91.5(3) . . . . ?
C9B N1B C8B C7B -117.1(3) . . . . ?
C6B C7B C8B N1B 179.5(2) . . . . ?
C8B N1B C9B C12B 173.7(2) . . . . ?
C8B N1B C9B C10B -5.9(5) . . . . ?
N1B C9B C10B O2B 0.3(5) . . . . ?
C12B C9B C10B O2B -179.4(3) . . . . ?
N1B C9B C10B C11B -179.8(3) . . . . ?
C12B C9B C10B C11B 0.5(2) . . . . ?
O2B C10B C11B O3B 0.5(6) . . . . ?
C9B C10B C11B O3B -179.4(3) . . . . ?
O2B C10B C11B C12B 179.4(3) . . . . ?
C9B C10B C11B C12B -0.5(2) . . . . ?
C13B N2B C12B C9B 173.2(2) . . . . ?
C13B N2B C12B C11B -8.3(4) . . . . ?
N1B C9B C12B N2B -1.2(5) . . . . ?
C10B C9B C12B N2B 178.5(3) . . . . ?
N1B C9B C12B C11B 179.8(3) . . . . ?
C10B C9B C12B C11B -0.5(2) . . . . ?
O3B C11B C12B N2B 0.4(6) . . . . ?
C10B C11B C12B N2B -178.5(3) . . . . ?
O3B C11B C12B C9B 179.4(3) . . . . ?
C10B C11B C12B C9B 0.5(2) . . . . ?
C12B N2B C13B C14B -99.6(3) . . . . ?
N2B C13B C14B C15B -170.3(2) . . . . ?
C13B C14B C15B C16B -101.2(3) . . . . ?
C13B C14B C15B C20B 80.8(3) . . . . ?
C20B C15B C16B C17B 2.7(4) . . . . ?
C14B C15B C16B C17B -175.3(2) . . . . ?
C15B C16B C17B C18B -1.4(4) . . . . ?
C16B C17B C18B C19B -1.8(4) . . . . ?
C16B C17B C18B O4B 176.7(2) . . . . ?
C17B C18B C19B C20B 3.5(4) . . . . ?
O4B C18B C19B C20B -175.0(2) . . . . ?
C18B C19B C20B C15B -2.1(4) . . . . ?
C16B C15B C20B C19B -1.0(4) . . . . ?
C14B C15B C20B C19B 177.1(2) . . . . ?
C6C C1C C2C C3C -1.6(4) . . . . ?
C1C C2C C3C C4C 2.7(4) . . . . ?
C1C C2C C3C O1C -177.5(2) . . . . ?
C2C C3C C4C C5C -2.3(5) . . . . ?
O1C C3C C4C C5C 177.9(2) . . . . ?
C3C C4C C5C C6C 0.8(5) . . . . ?
C2C C1C C6C C5C 0.1(4) . . . . ?
C2C C1C C6C C7C 178.7(2) . . . . ?
C4C C5C C6C C1C 0.3(4) . . . . ?
C4C C5C C6C C7C -178.3(2) . . . . ?
C1C C6C C7C C8C 82.7(3) . . . . ?
C5C C6C C7C C8C -98.8(3) . . . . ?
C9C N1C C8C C7C 115.9(2) . . . . ?
C6C C7C C8C N1C -178.1(2) . . . . ?
C8C N1C C9C C12C -175.0(2) . . . . ?
C8C N1C C9C C10C 6.8(4) . . . . ?
N1C C9C C10C O2C 1.0(6) . . . . ?
C12C C9C C10C O2C -177.7(3) . . . . ?
N1C C9C C10C C11C 178.6(3) . . . . ?
C12C C9C C10C C11C -0.2(2) . . . . ?
O2C C10C C11C O3C -2.1(6) . . . . ?
C9C C10C C11C O3C -179.6(3) . . . . ?
O2C C10C C11C C12C 177.7(3) . . . . ?
C9C C10C C11C C12C 0.1(2) . . . . ?
C13C N2C C12C C9C -173.5(2) . . . . ?
C13C N2C C12C C11C 7.8(5) . . . . ?
N1C C9C C12C N2C 2.3(5) . . . . ?
C10C C9C C12C N2C -178.9(3) . . . . ?
N1C C9C C12C C11C -178.6(3) . . . . ?
C10C C9C C12C C11C 0.2(2) . . . . ?
O3C C11C C12C N2C -1.3(5) . . . . ?
C10C C11C C12C N2C 178.9(3) . . . . ?
O3C C11C C12C C9C 179.6(3) . . . . ?
C10C C11C C12C C9C -0.2(2) . . . . ?
C12C N2C C13C C14C 108.5(3) . . . . ?
N2C C13C C14C C15C 172.6(2) . . . . ?
C13C C14C C15C C16C -87.1(3) . . . . ?
C13C C14C C15C C20C 90.6(3) . . . . ?
C20C C15C C16C C17C 0.0(4) . . . . ?
C14C C15C C16C C17C 177.8(2) . . . . ?
C15C C16C C17C C18C -0.3(4) . . . . ?
C16C C17C C18C C19C 1.0(4) . . . . ?
C16C C17C C18C O4C -179.3(2) . . . . ?
C17C C18C C19C C20C -1.4(4) . . . . ?
O4C C18C C19C C20C 178.9(2) . . . . ?
C18C C19C C20C C15C 1.1(4) . . . . ?
C16C C15C C20C C19C -0.4(4) . . . . ?
C14C C15C C20C C19C -178.2(2) . . . . ?
C6D C1D C2D C3D -1.3(4) . . . . ?
C1D C2D C3D C4D -0.2(4) . . . . ?
C1D C2D C3D O1D -179.6(2) . . . . ?
C2D C3D C4D C5D 1.1(5) . . . . ?
O1D C3D C4D C5D -179.6(2) . . . . ?
C3D C4D C5D C6D -0.5(4) . . . . ?
C2D C1D C6D C5D 1.8(4) . . . . ?
C2D C1D C6D C7D 179.7(2) . . . . ?
C4D C5D C6D C1D -0.9(4) . . . . ?
C4D C5D C6D C7D -178.9(2) . . . . ?
C1D C6D C7D C8D 93.9(3) . . . . ?
C5D C6D C7D C8D -88.3(3) . . . . ?
C9D N1D C8D C7D -119.2(3) . . . . ?
C6D C7D C8D N1D -178.7(2) . . . . ?
C8D N1D C9D C12D 173.5(2) . . . . ?
C8D N1D C9D C10D -6.5(5) . . . . ?
N1D C9D C10D O2D -0.5(5) . . . . ?
C12D C9D C10D O2D 179.5(3) . . . . ?
N1D C9D C10D C11D 179.8(3) . . . . ?
C12D C9D C10D C11D -0.1(2) . . . . ?
O2D C10D C11D O3D 1.5(6) . . . . ?
C9D C10D C11D O3D -178.9(3) . . . . ?
O2D C10D C11D C12D -179.5(3) . . . . ?
C9D C10D C11D C12D 0.1(2) . . . . ?
C13D N2D C12D C9D 175.4(3) . . . . ?
C13D N2D C12D C11D -6.8(4) . . . . ?
N1D C9D C12D N2D -1.4(5) . . . . ?
C10D C9D C12D N2D 178.5(3) . . . . ?
N1D C9D C12D C11D -179.8(3) . . . . ?
C10D C9D C12D C11D 0.1(2) . . . . ?
O3D C11D C12D N2D 0.5(6) . . . . ?
C10D C11D C12D N2D -178.6(3) . . . . ?
O3D C11D C12D C9D 178.9(3) . . . . ?
C10D C11D C12D C9D -0.1(2) . . . . ?
C12D N2D C13D C14D -107.7(3) . . . . ?
N2D C13D C14D C15D -179.5(2) . . . . ?
C13D C14D C15D C20D -90.1(3) . . . . ?
C13D C14D C15D C16D 92.3(3) . . . . ?
C20D C15D C16D C17D -2.0(4) . . . . ?
C14D C15D C16D C17D 175.7(2) . . . . ?
C15D C16D C17D C18D -0.4(4) . . . . ?
C16D C17D C18D C19D 3.1(4) . . . . ?
C16D C17D C18D O4D -177.5(2) . . . . ?
C17D C18D C19D C20D -3.2(4) . . . . ?
O4D C18D C19D C20D 177.4(2) . . . . ?
C18D C19D C20D C15D 0.7(4) . . . . ?
C16D C15D C20D C19D 1.9(4) . . . . ?
C14D C15D C20D C19D -175.8(2) . . . . ?
C6E C1E C2E C3E 1.1(4) . . . . ?
C1E C2E C3E C4E 0.1(4) . . . . ?
C1E C2E C3E O1E -179.4(2) . . . . ?
O1E C3E C4E C5E 178.6(2) . . . . ?
C2E C3E C4E C5E -0.9(4) . . . . ?
C3E C4E C5E C6E 0.5(4) . . . . ?
C2E C1E C6E C5E -1.4(4) . . . . ?
C2E C1E C6E C7E 178.8(2) . . . . ?
C4E C5E C6E C1E 0.7(4) . . . . ?
C4E C5E C6E C7E -179.5(2) . . . . ?
C1E C6E C7E C8E -92.3(3) . . . . ?
C5E C6E C7E C8E 87.9(3) . . . . ?
C9E N1E C8E C7E 114.4(3) . . . . ?
C6E C7E C8E N1E -179.8(2) . . . . ?
C8E N1E C9E C12E -172.1(3) . . . . ?
C8E N1E C9E C10E 8.4(4) . . . . ?
N1E C9E C10E O2E -0.1(6) . . . . ?
C12E C9E C10E O2E -179.8(4) . . . . ?
N1E C9E C10E C11E 179.5(3) . . . . ?
C12E C9E C10E C11E -0.2(2) . . . . ?
O2E C10E C11E O3E -0.6(6) . . . . ?
C9E C10E C11E O3E 179.8(3) . . . . ?
O2E C10E C11E C12E 179.8(4) . . . . ?
C9E C10E C11E C12E 0.2(2) . . . . ?
C13E N2E C12E C9E -172.3(2) . . . . ?
C13E N2E C12E C11E 9.2(5) . . . . ?
N1E C9E C12E N2E 1.6(5) . . . . ?
C10E C9E C12E N2E -178.7(3) . . . . ?
N1E C9E C12E C11E -179.5(3) . . . . ?
C10E C9E C12E C11E 0.2(2) . . . . ?
O3E C11E C12E N2E -0.9(6) . . . . ?
C10E C11E C12E N2E 178.7(3) . . . . ?
O3E C11E C12E C9E -179.8(3) . . . . ?
C10E C11E C12E C9E -0.2(2) . . . . ?
C12E N2E C13E C14E 99.3(3) . . . . ?
N2E C13E C14E C15E 169.6(2) . . . . ?
C13E C14E C15E C16E -77.2(4) . . . . ?
C13E C14E C15E C20E 102.9(3) . . . . ?
C20E C15E C16E C17E 0.7(4) . . . . ?
C14E C15E C16E C17E -179.1(2) . . . . ?
C15E C16E C17E C18E 0.7(4) . . . . ?
C16E C17E C18E C19E -1.7(4) . . . . ?
C16E C17E C18E O4E 179.8(2) . . . . ?
C17E C18E C19E C20E 1.3(4) . . . . ?
O4E C18E C19E C20E 179.8(2) . . . . ?
C18E C19E C20E C15E 0.1(4) . . . . ?
C16E C15E C20E C19E -1.1(4) . . . . ?
C14E C15E C20E C19E 178.7(2) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.038

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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. 
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#######################################################################

data_mo_023sb129_0ma_ab
_database_code_depnum_ccdc_archive 'CCDC 1539382'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 N O3'
_chemical_formula_sum            'C11 H10 N2 O3'
_chemical_formula_weight         218.21

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           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                   7.1055(13)
_cell_length_b                   10.956(2)
_cell_length_c                   14.797(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.699(7)
_cell_angle_gamma                90
_cell_volume                     1010.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    3494
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      28.10

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.256
_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  0.5775
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4251
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.433
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.553
_diffrn_measured_fraction_theta_full 0.539
_diffrn_reflns_Laue_measured_fraction_max 0.553
_diffrn_reflns_Laue_measured_fraction_full 0.539
_diffrn_reflns_point_group_measured_fraction_max 0.553
_diffrn_reflns_point_group_measured_fraction_full 0.539
_reflns_number_total             988
_reflns_number_gt                856
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 2008)'
_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)+(0.0837P)²+0.7910P]
 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         988
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1707
_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
O1 O 0.3943(6) 0.4101(2) 0.3479(2) 0.0512(10) Uani 1 1 d . . . . .
O2 O 0.1147(7) 0.3821(3) 0.4650(3) 0.0608(12) Uani 1 1 d . . . . .
O3 O 0.2538(6) 0.0982(2) 0.5103(3) 0.0518(10) Uani 1 1 d . . . . .
N1 N 0.5381(7) 0.1225(3) 0.3958(3) 0.0467(11) Uani 1 1 d . . . . .
H1N H 0.5382 0.0463 0.4100 0.056 Uiso 1 1 calc R U . . .
N2 N 0.7588(7) 0.1304(3) 0.1516(3) 0.0427(10) Uani 1 1 d . . . . .
H2N H 0.7172 0.0563 0.1499 0.051 Uiso 1 1 calc R U . . .
C1 C 0.3501(8) 0.3236(3) 0.3909(3) 0.0382(10) Uani 1 1 d . . . . .
C2 C 0.2183(8) 0.3134(3) 0.4438(3) 0.0392(11) Uani 1 1 d . . . . .
C3 C 0.2888(8) 0.1835(3) 0.4664(3) 0.0369(10) Uani 1 1 d . . . . .
C4 C 0.4125(7) 0.1989(3) 0.4131(3) 0.0336(10) Uani 1 1 d . . . . .
C5 C 0.6768(8) 0.1643(4) 0.3529(3) 0.0459(12) Uani 1 1 d . . . . .
H5 H 0.7910 0.1056 0.3695 0.055 Uiso 1 1 calc R U . . .
H5A H 0.7416 0.2419 0.3837 0.055 Uiso 1 1 calc R U . . .
C6 C 0.5459(9) 0.1785(4) 0.2364(3) 0.0446(11) Uani 1 1 d . . . . .
H6 H 0.4760 0.1019 0.2055 0.054 Uiso 1 1 calc R U . . .
H6A H 0.4360 0.2401 0.2195 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6937(8) 0.2155(3) 0.1947(3) 0.0367(10) Uani 1 1 d . . . . .
C8 C 0.7639(9) 0.3330(3) 0.2000(3) 0.0452(12) Uani 1 1 d . . . . .
H8 H 0.7219 0.3937 0.2305 0.054 Uiso 1 1 calc R U . . .
C9 C 0.8979(10) 0.3603(4) 0.1595(4) 0.0539(14) Uani 1 1 d . . . . .
H9 H 0.9454 0.4400 0.1621 0.065 Uiso 1 1 calc R U . . .
C10 C 0.9616(10) 0.2698(4) 0.1150(4) 0.0539(14) Uani 1 1 d . . . . .
H10 H 1.0540 0.2871 0.0887 0.065 Uiso 1 1 calc R U . . .
C11 C 0.8864(9) 0.1558(4) 0.1108(3) 0.0462(12) Uani 1 1 d . . . . .
H11 H 0.9237 0.0942 0.0791 0.055 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 C1 1.262(4) . ?
O2 C2 1.195(5) . ?
O3 C3 1.230(4) . ?
N1 C4 1.336(5) . ?
N1 C5 1.478(5) . ?
N1 H1N 0.8600 . ?
N2 C7 1.332(5) . ?
N2 C11 1.338(5) . ?
N2 H2N 0.8600 . ?
C1 C4 1.425(6) . ?
C1 C2 1.486(5) . ?
C2 C3 1.493(5) . ?
C3 C4 1.445(5) . ?
C5 C6 1.525(6) . ?
C5 H5 0.9700 . ?
C5 H5A 0.9700 . ?
C6 C7 1.507(5) . ?
C6 H6 0.9700 . ?
C6 H6A 0.9700 . ?
C7 C8 1.370(5) . ?
C8 C9 1.379(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.380(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.348(6) . ?
C10 H10 0.9300 . ?
C11 H11 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
C4 N1 C5 122.2(3) . . ?
C4 N1 H1N 118.9 . . ?
C5 N1 H1N 118.9 . . ?
C7 N2 C11 122.5(4) . . ?
C7 N2 H2N 118.8 . . ?
C11 N2 H2N 118.8 . . ?
O1 C1 C4 135.3(3) . . ?
O1 C1 C2 134.0(3) . . ?
C4 C1 C2 90.6(3) . . ?
O2 C2 C1 135.6(3) . . ?
O2 C2 C3 136.5(3) . . ?
C1 C2 C3 87.7(3) . . ?
O3 C3 C4 135.1(4) . . ?
O3 C3 C2 135.3(3) . . ?
C4 C3 C2 89.6(3) . . ?
N1 C4 C1 136.0(3) . . ?
N1 C4 C3 132.0(3) . . ?
C1 C4 C3 92.0(3) . . ?
N1 C5 C6 110.3(4) . . ?
N1 C5 H5 109.6 . . ?
C6 C5 H5 109.6 . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
H5 C5 H5A 108.1 . . ?
C7 C6 C5 108.9(4) . . ?
C7 C6 H6 109.9 . . ?
C5 C6 H6 109.9 . . ?
C7 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
H6 C6 H6A 108.3 . . ?
N2 C7 C8 119.0(3) . . ?
N2 C7 C6 118.6(3) . . ?
C8 C7 C6 122.4(3) . . ?
C7 C8 C9 119.2(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N2 C11 C10 120.7(4) . . ?
N2 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.042



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_annm61b
_database_code_depnum_ccdc_archive 'CCDC 1539383'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   7.435(5)
_cell_length_b                   14.028(7)
_cell_length_c                   12.008(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.07(3)
_cell_angle_gamma                90.00
_cell_volume                     1251.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    216
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11149
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         30.33
_reflns_number_total             3058
_reflns_number_gt                2598
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MARXDS
_computing_cell_refinement       AUTOMAR
_computing_data_reduction        MARSCALE
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.1199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.045(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     164
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.171
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.24187(14) 0.34894(7) 0.17897(8) 0.0645(3) Uani 1 1 d . . .
O2 O -0.10825(13) 0.55945(7) 0.26964(8) 0.0630(3) Uani 1 1 d . . .
O3 O 0.07917(12) 0.25278(6) 0.34078(8) 0.0548(2) Uani 1 1 d U . .
N1 N 0.19706(15) 0.45758(8) 0.42927(9) 0.0556(3) Uani 1 1 d . . .
H1 H 0.2047 0.5177 0.4429 0.067 Uiso 1 1 calc R . .
N2 N 0.73751(15) 0.33267(8) 0.53349(9) 0.0563(3) Uani 1 1 d U . .
C1 C -0.0648(2) 0.47615(11) 0.28595(12) 0.0625(4) Uani 1 1 d . . .
C2 C -0.1270(2) 0.38032(12) 0.24519(13) 0.0650(4) Uani 1 1 d . . .
C3 C 0.0152(2) 0.33898(10) 0.31766(12) 0.0594(3) Uani 1 1 d U . .
C4 C 0.07360(18) 0.42716(10) 0.35642(11) 0.0577(3) Uani 1 1 d . . .
C5 C -0.0170(2) 0.17266(11) 0.28877(13) 0.0675(4) Uani 1 1 d U . .
H5A H -0.0160 0.1782 0.2083 0.081 Uiso 1 1 calc R . .
H5B H -0.1412 0.1724 0.3109 0.081 Uiso 1 1 calc R . .
C6 C 0.0738(2) 0.08318(12) 0.32527(15) 0.0771(4) Uani 1 1 d . . .
H6A H 0.0122 0.0296 0.2918 0.116 Uiso 1 1 calc R . .
H6B H 0.0715 0.0781 0.4049 0.116 Uiso 1 1 calc R . .
H6C H 0.1963 0.0839 0.3027 0.116 Uiso 1 1 calc R . .
C7 C 0.32176(19) 0.39241(10) 0.48789(11) 0.0593(3) Uani 1 1 d . . .
H7A H 0.2564 0.3367 0.5120 0.071 Uiso 1 1 calc R . .
H7B H 0.3729 0.4238 0.5537 0.071 Uiso 1 1 calc R . .
C8 C 0.4738(2) 0.36108(11) 0.41328(12) 0.0620(3) Uani 1 1 d . . .
H8A H 0.4227 0.3304 0.3470 0.074 Uiso 1 1 calc R . .
H8B H 0.5403 0.4167 0.3900 0.074 Uiso 1 1 calc R . .
C9 C 0.60036(18) 0.29289(10) 0.47381(11) 0.0575(3) Uani 1 1 d . . .
C10 C 0.5766(2) 0.19578(11) 0.47057(13) 0.0677(4) Uani 1 1 d . . .
H10 H 0.4807 0.1699 0.4289 0.081 Uiso 1 1 calc R . .
C11 C 0.6940(2) 0.13649(12) 0.52866(14) 0.0713(4) Uani 1 1 d . . .
H11 H 0.6779 0.0708 0.5265 0.086 Uiso 1 1 calc R . .
C12 C 0.8340(2) 0.17529(11) 0.58936(13) 0.0658(4) Uani 1 1 d . . .
H12 H 0.9162 0.1372 0.6290 0.079 Uiso 1 1 calc R . .
C13 C 0.8495(2) 0.27575(11) 0.58965(12) 0.0638(4) Uani 1 1 d U . .
H13 H 0.9434 0.3032 0.6316 0.077 Uiso 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
O1 C2 1.2272(18) . ?
O2 C1 1.2262(18) . ?
O3 C3 1.3250(17) . ?
O3 C5 1.4604(18) . ?
N1 C4 1.3160(18) . ?
N1 C7 1.4642(18) . ?
N1 H1 0.8600 . ?
N2 C13 1.3209(19) . ?
N2 C9 1.3461(18) . ?
C1 C4 1.478(2) . ?
C1 C2 1.498(2) . ?
C2 C3 1.465(2) . ?
C3 C4 1.386(2) . ?
C5 C6 1.484(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.532(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.374(2) . ?
C10 C11 1.377(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.363(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.414(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
C3 O3 C5 116.51(12) . . ?
C4 N1 C7 122.10(12) . . ?
C4 N1 H1 119.0 . . ?
C7 N1 H1 119.0 . . ?
C13 N2 C9 118.19(13) . . ?
O2 C1 C4 135.10(14) . . ?
O2 C1 C2 136.61(14) . . ?
C4 C1 C2 88.29(12) . . ?
O1 C2 C3 135.52(16) . . ?
O1 C2 C1 137.13(15) . . ?
C3 C2 C1 87.33(12) . . ?
O3 C3 C4 129.69(14) . . ?
O3 C3 C2 137.02(13) . . ?
C4 C3 C2 93.26(12) . . ?
N1 C4 C3 135.66(13) . . ?
N1 C4 C1 133.18(14) . . ?
C3 C4 C1 91.12(12) . . ?
O3 C5 C6 108.31(13) . . ?
O3 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O3 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 C8 111.45(12) . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 111.13(12) . . ?
C9 C8 H8A 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C10 121.34(13) . . ?
N2 C9 C8 116.15(13) . . ?
C10 C9 C8 122.50(13) . . ?
C9 C10 C11 120.42(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 119.19(16) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 117.38(14) . . ?
C11 C12 H12 121.3 . . ?
C13 C12 H12 121.3 . . ?
N2 C13 C12 123.48(14) . . ?
N2 C13 H13 118.3 . . ?
C12 C13 H13 118.3 . . ?

_diffrn_measured_fraction_theta_max 0.812
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.944
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_anpm67b
_audit_block_doi                 10.5517/cc132w02
_database_code_depnum_ccdc_archive 'CCDC 1015653'
_audit_update_record             
;
2017-03-21 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O4, C2 H6 O'
_chemical_formula_sum            'C44 H52 N4 O10'
_chemical_formula_weight         796.89

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   46.922(5)
_cell_length_b                   6.086(4)
_cell_length_c                   7.467(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.72(6)
_cell_angle_gamma                90
_cell_volume                     2130(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    124
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 The ?Alert A? is due to it has been collected 89.7% 
 of the reflections . 
 This is due to the crystal does not diffract 
 very well and for the of detector that was used 
 (missing data due to data collection by rotation 
 around the spindle axis only ?image-plate detector?)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6362
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -69
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_max         32.315
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.698
_diffrn_measured_fraction_theta_full 0.897
_diffrn_reflns_Laue_measured_fraction_max 0.698
_diffrn_reflns_Laue_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.503
_diffrn_reflns_point_group_measured_fraction_full 0.716
_reflns_number_total             3820
_reflns_number_gt                2042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.439
_reflns_Friedel_fraction_max     0.307
_reflns_Friedel_fraction_full    0.535

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'MARXDS (Claudio Klein, 2005)'
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'


_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)+(0.1363P)²]
 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       .

_chemical_absolute_configuration rm
_refine_ls_number_reflns         3820
_refine_ls_number_parameters     241
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2424
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      1.002
_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 0.21355(14) 0.2264(10) -0.0269(9) 0.0755(16) Uani 1 1 d . . . . .
H1O H 0.2052 0.1195 0.0123 0.113 Uiso 1 1 calc R U . . .
O2 O 0.37999(15) -0.2874(8) 0.1458(9) 0.0688(16) Uani 1 1 d . U . . .
O3 O 0.44346(12) -0.2796(7) 0.3435(8) 0.0442(10) Uani 1 1 d . U . . .
O4 O 0.60865(15) 0.1432(10) 0.5205(8) 0.0748(16) Uani 1 1 d . . . . .
H4O H 0.6154 0.2378 0.5883 0.112 Uiso 1 1 calc R U . . .
N1 N 0.37864(15) 0.2627(10) 0.1580(9) 0.0521(15) Uani 1 1 d . . . . .
H1 H 0.3840 0.3973 0.1702 0.063 Uiso 1 1 calc R U . . .
N2 N 0.44269(14) 0.2496(8) 0.3482(8) 0.0376(11) Uani 1 1 d . . . . .
H2 H 0.4365 0.3824 0.3513 0.045 Uiso 1 1 calc R U . . .
C1 C 0.28390(12) 0.0805(7) 0.1898(7) 0.0450(15) Uani 1 1 d G . . . .
H1A H 0.2930 -0.0283 0.2587 0.054 Uiso 1 1 calc R U . . .
C2 C 0.25579(12) 0.0515(7) 0.1268(8) 0.068(2) Uani 1 1 d G . . . .
H2A H 0.2461 -0.0767 0.1536 0.082 Uiso 1 1 calc R U . . .
C3 C 0.24220(11) 0.2142(9) 0.0238(8) 0.067(2) Uani 1 1 d G . . . .
C4 C 0.25670(12) 0.4058(8) -0.0162(8) 0.060(2) Uani 1 1 d G . . . .
H4 H 0.2476 0.5146 -0.0852 0.071 Uiso 1 1 calc R U . . .
C5 C 0.28481(12) 0.4348(7) 0.0467(8) 0.0464(15) Uani 1 1 d G . . . .
H5 H 0.2945 0.5630 0.0199 0.056 Uiso 1 1 calc R U . . .
C6 C 0.29840(10) 0.2722(8) 0.1498(8) 0.0463(16) Uani 1 1 d G . . . .
C7 C 0.32914(16) 0.2987(12) 0.2193(10) 0.0546(18) Uani 1 1 d . U . . .
H7A H 0.3318 0.2172 0.3305 0.066 Uiso 1 1 calc R U . . .
H7B H 0.3325 0.4526 0.2465 0.066 Uiso 1 1 calc R U . . .
C8 C 0.35169(16) 0.2206(11) 0.0891(9) 0.0473(15) Uani 1 1 d . U . . .
H8A H 0.3495 0.0640 0.0681 0.057 Uiso 1 1 calc R U . . .
H8B H 0.3487 0.2955 -0.0249 0.057 Uiso 1 1 calc R U . . .
C9 C 0.39715(16) 0.1035(9) 0.2075(9) 0.0318(10) Uani 1 1 d . U . . .
C10 C 0.39659(15) -0.1388(8) 0.1973(8) 0.0257(9) Uani 1 1 d . U . . .
C11 C 0.42494(19) -0.1453(14) 0.2826(13) 0.059(2) Uani 1 1 d . U . . .
C12 C 0.42563(18) 0.0869(12) 0.2879(10) 0.0454(15) Uani 1 1 d . U . . .
C13 C 0.47317(15) 0.1972(12) 0.4110(10) 0.0472(16) Uani 1 1 d . . . . .
H13A H 0.4768 0.2502 0.5325 0.057 Uiso 1 1 calc R U . . .
H13B H 0.4762 0.0396 0.4102 0.057 Uiso 1 1 calc R U . . .
C14 C 0.49267(19) 0.3053(13) 0.2890(10) 0.061(2) Uani 1 1 d . . . . .
H14A H 0.4888 0.4619 0.2865 0.073 Uiso 1 1 calc R U . . .
H14B H 0.4891 0.2486 0.1685 0.073 Uiso 1 1 calc R U . . .
C15 C 0.52472(11) 0.2662(10) 0.3484(8) 0.0569(19) Uani 1 1 d G . . . .
C16 C 0.53870(13) 0.0735(9) 0.3048(8) 0.070(2) Uani 1 1 d G . . . .
H16 H 0.5290 -0.0350 0.2386 0.084 Uiso 1 1 calc R U . . .
C17 C 0.56713(13) 0.0430(9) 0.3601(9) 0.078(3) Uani 1 1 d G . . . .
H17 H 0.5765 -0.0859 0.3309 0.093 Uiso 1 1 calc R U . . .
C18 C 0.58157(11) 0.2053(12) 0.4590(9) 0.074(3) Uani 1 1 d G . . . .
C19 C 0.56759(14) 0.3980(10) 0.5026(9) 0.076(3) Uani 1 1 d G . . . .
H19 H 0.5773 0.5065 0.5688 0.091 Uiso 1 1 calc R U . . .
C20 C 0.53916(14) 0.4285(9) 0.4473(8) 0.074(2) Uani 1 1 d G . . . .
H20 H 0.5298 0.5574 0.4764 0.088 Uiso 1 1 calc R U . . .
O1W O 0.19597(8) -0.2161(12) 0.1148(6) 0.109(2) Uani 1 1 d D . . . .
H1W H 0.1966(4) -0.162(4) 0.2270(13) 0.164 Uiso 1 1 d D U . . .
C1W C 0.16880(10) -0.3066(18) 0.0496(10) 0.112(4) Uani 1 1 d D . . . .
H1W1 H 0.1606 -0.3781 0.1513 0.135 Uiso 1 1 calc R U . . .
H1W2 H 0.1732 -0.4222 -0.0341 0.135 Uiso 1 1 calc R U . . .
C2W C 0.1443(3) -0.167(2) -0.0433(18) 0.181(9) Uani 1 1 d D . . . .
H2W1 H 0.1285 -0.2608 -0.0763 0.271 Uiso 1 1 calc R U . . .
H2W2 H 0.1512 -0.0982 -0.1487 0.271 Uiso 1 1 calc R U . . .
H2W3 H 0.1383 -0.0560 0.0382 0.271 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 C3 1.381(6) . ?
O1 H1O 0.8200 . ?
O2 C10 1.242(7) . ?
O3 C11 1.262(9) . ?
O4 C18 1.383(7) . ?
O4 H4O 0.8200 . ?
N1 C9 1.341(8) . ?
N1 C8 1.367(9) . ?
N1 H1 0.8600 . ?
N2 C12 1.338(8) . ?
N2 C13 1.518(9) . ?
N2 H2 0.8600 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 H1A 0.9300 . ?
C2 C3 1.3900 . ?
C2 H2A 0.9300 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.518(7) . ?
C7 C8 1.545(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C12 1.442(6) . ?
C9 C10 1.477(8) . ?
C10 C11 1.448(7) . ?
C10 C12 2.028(9) . ?
C11 C12 1.414(11) . ?
C13 C14 1.476(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.565(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C16 H16 0.9300 . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1W C1W 1.4512(18) . ?
O1W H1W 0.9000(15) . ?
C1W C2W 1.564(9) . ?
C1W H1W1 0.9700 . ?
C1W H1W2 0.9700 . ?
C2W H2W1 0.9600 . ?
C2W H2W2 0.9600 . ?
C2W H2W3 0.9600 . ?

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
C3 O1 H1O 109.5 . . ?
C18 O4 H4O 109.5 . . ?
C9 N1 C8 122.9(6) . . ?
C9 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C12 N2 C13 119.2(5) . . ?
C12 N2 H2 120.4 . . ?
C13 N2 H2 120.4 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
O1 C3 C4 112.1(4) . . ?
O1 C3 C2 127.2(4) . . ?
C4 C3 C2 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 121.1(4) . . ?
C1 C6 C7 118.9(4) . . ?
C6 C7 C8 114.8(5) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
N1 C8 C7 110.8(5) . . ?
N1 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N1 C9 C12 137.8(7) . . ?
N1 C9 C10 134.2(6) . . ?
C12 C9 C10 88.0(5) . . ?
O2 C10 C11 131.7(7) . . ?
O2 C10 C9 138.8(6) . . ?
C11 C10 C9 89.5(6) . . ?
O2 C10 C12 175.9(5) . . ?
C11 C10 C12 44.2(4) . . ?
C9 C10 C12 45.3(3) . . ?
O3 C11 C12 128.5(7) . . ?
O3 C11 C10 141.1(8) . . ?
C12 C11 C10 90.3(6) . . ?
N2 C12 C11 139.6(6) . . ?
N2 C12 C9 128.0(7) . . ?
C11 C12 C9 92.2(6) . . ?
N2 C12 C10 174.5(6) . . ?
C11 C12 C10 45.5(4) . . ?
C9 C12 C10 46.7(4) . . ?
C14 C13 N2 108.6(6) . . ?
C14 C13 H13A 110.0 . . ?
N2 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
N2 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
C13 C14 C15 111.9(6) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C20 120.0 . . ?
C16 C15 C14 121.3(5) . . ?
C20 C15 C14 118.7(5) . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O4 C18 C19 126.1(5) . . ?
O4 C18 C17 113.5(5) . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C20 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C1W O1W H1W 116.0(12) . . ?
O1W C1W C2W 123.9(8) . . ?
O1W C1W H1W1 106.4 . . ?
C2W C1W H1W1 106.4 . . ?
O1W C1W H1W2 106.4 . . ?
C2W C1W H1W2 106.4 . . ?
H1W1 C1W H1W2 106.4 . . ?
C1W C2W H2W1 109.5 . . ?
C1W C2W H2W2 109.5 . . ?
H2W1 C2W H2W2 109.5 . . ?
C1W C2W H2W3 109.5 . . ?
H2W1 C2W H2W3 109.5 . . ?
H2W2 C2W H2W3 109.5 . . ?

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.064



