# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_datam_a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.32

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

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

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

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

_cell_length_a                   8.4042(8)
_cell_length_b                   9.8413(9)
_cell_length_c                   10.3659(9)
_cell_angle_alpha                76.975(3)
_cell_angle_beta                 72.998(3)
_cell_angle_gamma                77.774(3)
_cell_volume                     788.93(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27639
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3226
_reflns_number_gt                2618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 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         3226
_refine_ls_number_parameters     228
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_restrained_S_all      1.238
_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 0.22655(12) 0.45696(10) 0.48113(10) 0.0462(3) Uani 1 1 d . U . . .
O3 O 0.33443(13) 0.09699(12) 0.23403(10) 0.0504(3) Uani 1 1 d . U . . .
N1 N 0.50624(14) 0.25575(11) 0.50167(11) 0.0346(3) Uani 1 1 d . U . . .
O4 O 0.54930(15) 0.18305(14) 0.07646(10) 0.0603(4) Uani 1 1 d . U . . .
O2 O 0.22406(14) 0.39780(12) 0.28882(11) 0.0574(3) Uani 1 1 d . U . . .
C8 C 0.43328(16) 0.26805(14) 0.39628(13) 0.0353(3) Uani 1 1 d . U . . .
C5 C 0.43478(17) 0.33650(14) 0.60584(14) 0.0364(3) Uani 1 1 d . U . . .
C11 C 0.66127(16) 0.09898(13) 0.37031(13) 0.0336(3) Uani 1 1 d . U . . .
C10 C 0.52526(16) 0.17183(14) 0.31414(13) 0.0346(3) Uani 1 1 d . U . . .
C15 C 0.79476(16) -0.01706(14) 0.32423(13) 0.0347(3) Uani 1 1 d . U . . .
C13 C 0.47525(17) 0.15313(15) 0.19351(14) 0.0387(3) Uani 1 1 d . U . . .
C12 C 0.64358(16) 0.15350(13) 0.48611(13) 0.0359(3) Uani 1 1 d . U . . .
H12 H 0.7147 0.1247 0.5444 0.043 Uiso 1 1 calc R U . . .
C6 C 0.29260(17) 0.43546(15) 0.59292(14) 0.0389(3) Uani 1 1 d . U . . .
C9 C 0.28952(18) 0.37519(15) 0.38164(15) 0.0403(4) Uani 1 1 d . U . . .
C16 C 0.88493(18) -0.10282(15) 0.41367(15) 0.0414(4) Uani 1 1 d . U . . .
H16 H 0.8621 -0.0852 0.5023 0.050 Uiso 1 1 calc R U . . .
C4 C 0.49443(19) 0.32166(16) 0.71978(15) 0.0459(4) Uani 1 1 d . U . . .
H4 H 0.5889 0.2555 0.7302 0.055 Uiso 1 1 calc R U . . .
C7 C 0.21151(19) 0.51666(16) 0.69279(17) 0.0462(4) Uani 1 1 d . U . . .
H7 H 0.1154 0.5811 0.6836 0.055 Uiso 1 1 calc R U . . .
C2 C 0.2718(2) 0.50299(17) 0.80614(16) 0.0472(4) Uani 1 1 d . U . . .
C20 C 0.8356(2) -0.04512(17) 0.19230(16) 0.0490(4) Uani 1 1 d . U . . .
H20 H 0.7795 0.0118 0.1293 0.059 Uiso 1 1 calc R U . . .
C17 C 1.00737(19) -0.21331(16) 0.37360(16) 0.0486(4) Uani 1 1 d . U . . .
H17 H 1.0660 -0.2692 0.4353 0.058 Uiso 1 1 calc R U . . .
C18 C 1.0439(2) -0.24198(17) 0.24322(18) 0.0513(4) Uani 1 1 d . U . . .
H18 H 1.1251 -0.3179 0.2169 0.062 Uiso 1 1 calc R U . . .
C3 C 0.4143(2) 0.40469(17) 0.81824(16) 0.0508(4) Uani 1 1 d . U . . .
H3 H 0.4565 0.3946 0.8940 0.061 Uiso 1 1 calc R U . . .
C19 C 0.9588(2) -0.15676(19) 0.15290(18) 0.0573(5) Uani 1 1 d . U . . .
H19 H 0.9840 -0.1741 0.0640 0.069 Uiso 1 1 calc R U . . .
C1 C 0.1852(2) 0.5927(2) 0.91489(18) 0.0648(5) Uani 1 1 d . U . . .
H1A H 0.2522 0.6631 0.9081 0.097 Uiso 1 1 calc R U . . .
H1B H 0.1717 0.5340 1.0038 0.097 Uiso 1 1 calc R U . . .
H1C H 0.0766 0.6380 0.9020 0.097 Uiso 1 1 calc R U . . .
C14 C 0.2599(2) 0.0902(2) 0.12733(19) 0.0709(6) Uani 1 1 d . U . . .
H14A H 0.2496 0.1811 0.0697 0.106 Uiso 1 1 calc R U . . .
H14B H 0.1504 0.0632 0.1677 0.106 Uiso 1 1 calc R U . . .
H14C H 0.3301 0.0218 0.0735 0.106 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 C9 1.3659(17) . ?
O1 C6 1.3826(17) . ?
O3 C13 1.3282(18) . ?
O3 C14 1.441(2) . ?
N1 C12 1.3577(15) . ?
N1 C8 1.3729(17) . ?
N1 C5 1.4013(17) . ?
O4 C13 1.1921(17) . ?
O2 C9 1.1997(17) . ?
C8 C10 1.3739(18) . ?
C8 C9 1.4457(19) . ?
C5 C4 1.380(2) . ?
C5 C6 1.391(2) . ?
C11 C12 1.3795(18) . ?
C11 C10 1.4190(18) . ?
C11 C15 1.4767(18) . ?
C10 C13 1.4894(19) . ?
C15 C20 1.386(2) . ?
C15 C16 1.390(2) . ?
C6 C7 1.380(2) . ?
C16 C17 1.3760(19) . ?
C4 C3 1.380(2) . ?
C7 C2 1.380(2) . ?
C2 C3 1.389(2) . ?
C2 C1 1.509(2) . ?
C20 C19 1.385(2) . ?
C17 C18 1.376(2) . ?
C18 C19 1.370(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
C9 O1 C6 121.91(11) . . ?
C13 O3 C14 116.06(12) . . ?
C12 N1 C8 108.44(11) . . ?
C12 N1 C5 130.11(11) . . ?
C8 N1 C5 121.38(11) . . ?
N1 C8 C10 108.54(11) . . ?
N1 C8 C9 120.78(12) . . ?
C10 C8 C9 130.58(13) . . ?
C4 C5 C6 118.89(13) . . ?
C4 C5 N1 124.23(12) . . ?
C6 C5 N1 116.87(13) . . ?
C12 C11 C10 106.29(12) . . ?
C12 C11 C15 124.09(12) . . ?
C10 C11 C15 129.57(13) . . ?
C8 C10 C11 107.33(12) . . ?
C8 C10 C13 122.26(12) . . ?
C11 C10 C13 130.37(13) . . ?
C20 C15 C16 117.45(13) . . ?
C20 C15 C11 122.19(12) . . ?
C16 C15 C11 120.36(12) . . ?
O4 C13 O3 123.78(13) . . ?
O4 C13 C10 125.85(14) . . ?
O3 C13 C10 110.37(11) . . ?
N1 C12 C11 109.39(11) . . ?
C7 C6 O1 117.23(13) . . ?
C7 C6 C5 120.66(14) . . ?
O1 C6 C5 122.11(13) . . ?
O2 C9 O1 118.45(12) . . ?
O2 C9 C8 124.95(14) . . ?
O1 C9 C8 116.60(12) . . ?
C17 C16 C15 121.26(14) . . ?
C3 C4 C5 120.18(14) . . ?
C2 C7 C6 120.56(14) . . ?
C7 C2 C3 118.58(14) . . ?
C7 C2 C1 120.89(16) . . ?
C3 C2 C1 120.52(16) . . ?
C19 C20 C15 120.89(14) . . ?
C18 C17 C16 120.68(14) . . ?
C19 C18 C17 118.83(14) . . ?
C4 C3 C2 121.12(15) . . ?
C18 C19 C20 120.86(15) . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 982192'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DATAM2_A

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N2 O10 S'
_chemical_formula_sum            'C19 H18 N2 O10 S'
_chemical_formula_weight         466.42

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                   7.2807(3)
_cell_length_b                   23.1644(11)
_cell_length_c                   12.4215(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.8900(14)
_cell_angle_gamma                90
_cell_volume                     2069.76(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1026
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67985
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4229
_reflns_number_gt                3429
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 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         4229
_refine_ls_number_parameters     289
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2480
_refine_ls_wR_factor_gt          0.2406
_refine_ls_goodness_of_fit_ref   1.999
_refine_ls_restrained_S_all      1.982
_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
S001 S 0.61396(11) 0.76079(3) 0.53337(8) 0.0582(3) Uani 1 1 d . U . . .
O12 O 0.7943(3) -0.00948(8) 1.10353(15) 0.0431(5) Uani 1 1 d . U . . .
O3 O 0.7537(3) 0.13829(8) 0.80375(16) 0.0493(6) Uani 1 1 d . U . . .
O2 O 0.8466(3) 0.05761(9) 0.72937(16) 0.0527(6) Uani 1 1 d . U . . .
O7 O 0.6650(3) -0.08376(9) 1.01372(18) 0.0530(6) Uani 1 1 d . U . . .
O1 O 1.0471(3) 0.21354(10) 1.14523(19) 0.0625(7) Uani 1 1 d . U . . .
H1A H 1.0102 0.2330 1.0910 0.094 Uiso 1 1 calc R U . . .
O007 O 0.5361(3) -0.11527(9) 0.6851(2) 0.0599(7) Uani 1 1 d . U . . .
H00A H 0.4994 -0.1400 0.6396 0.090 Uiso 1 1 calc R U . . .
O1W O 0.9295(3) 0.27926(11) 0.9695(2) 0.0644(7) Uani 1 1 d . . . . .
N2 N 0.6150(3) -0.03260(10) 0.8231(2) 0.0437(6) Uani 1 1 d . U . . .
H2A H 0.6347 -0.0691 0.8310 0.052 Uiso 1 1 calc R U . . .
O6 O 0.4490(3) 0.79522(10) 0.5592(3) 0.0783(9) Uani 1 1 d . U . . .
O4 O 0.1069(3) 0.10414(11) 0.49680(19) 0.0651(7) Uani 1 1 d . U . . .
O5 O 0.2670(4) 0.13875(10) 0.6424(2) 0.0700(8) Uani 1 1 d . U . . .
N1 N 0.2218(4) 0.09852(11) 0.5797(2) 0.0463(6) Uani 1 1 d . U . . .
C5 C 0.8455(3) 0.08046(11) 1.0136(2) 0.0309(6) Uani 1 1 d . U . . .
C15 C 0.7726(3) 0.05360(11) 0.9092(2) 0.0309(6) Uani 1 1 d . U . . .
C18 C 0.6994(3) -0.00057(10) 0.9088(2) 0.0332(6) Uani 1 1 d . U . . .
C00H C 0.7960(4) 0.08201(11) 0.8048(2) 0.0349(6) Uani 1 1 d . U . . .
C7 C 0.4241(4) 0.03522(11) 0.7018(2) 0.0344(6) Uani 1 1 d . U . . .
H7A H 0.4492 0.0659 0.7502 0.041 Uiso 1 1 calc R U . . .
C14 C 0.7171(4) -0.03464(12) 1.0108(2) 0.0378(6) Uani 1 1 d . U . . .
C6 C 0.9137(4) 0.13740(11) 1.0272(2) 0.0365(6) Uani 1 1 d . U . . .
H6B H 0.9129 0.1610 0.9666 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8543(4) 0.04748(12) 1.1071(2) 0.0355(6) Uani 1 1 d . U . . .
C12 C 0.5036(4) -0.01824(12) 0.7256(2) 0.0359(6) Uani 1 1 d . U . . .
C8 C 0.3053(4) 0.04217(12) 0.6035(2) 0.0372(6) Uani 1 1 d . U . . .
C9 C 0.2635(4) -0.00200(13) 0.5302(2) 0.0438(7) Uani 1 1 d . U . . .
H9A H 0.1847 0.0040 0.4647 0.053 Uiso 1 1 calc R U . . .
C11 C 0.4605(4) -0.06376(12) 0.6521(2) 0.0419(7) Uani 1 1 d . U . . .
C10 C 0.3404(4) -0.05504(13) 0.5555(2) 0.0457(7) Uani 1 1 d . U . . .
H10A H 0.3119 -0.0856 0.5073 0.055 Uiso 1 1 calc R U . . .
C1 C 0.9817(4) 0.15839(12) 1.1296(2) 0.0424(7) Uani 1 1 d . U . . .
C3 C 0.9242(4) 0.06761(14) 1.2095(2) 0.0462(7) Uani 1 1 d . U . . .
H3A H 0.9282 0.0438 1.2701 0.055 Uiso 1 1 calc R U . . .
C2 C 0.9885(4) 0.12395(13) 1.2207(2) 0.0478(8) Uani 1 1 d . U . . .
H2B H 1.0359 0.1384 1.2892 0.057 Uiso 1 1 calc R U . . .
C17 C 0.7939(6) 0.17058(15) 0.7101(3) 0.0687(11) Uani 1 1 d . U . . .
H17A H 0.7589 0.2102 0.7168 0.103 Uiso 1 1 calc R U . . .
H17B H 0.7250 0.1545 0.6448 0.103 Uiso 1 1 calc R U . . .
H17C H 0.9245 0.1684 0.7065 0.103 Uiso 1 1 calc R U . . .
C22 C 0.5230(6) 0.71188(17) 0.4312(3) 0.0727(11) Uani 1 1 d . U . . .
H22A H 0.4830 0.7324 0.3646 0.109 Uiso 1 1 calc R U . . .
H22B H 0.4190 0.6920 0.4529 0.109 Uiso 1 1 calc R U . . .
H22C H 0.6170 0.6844 0.4202 0.109 Uiso 1 1 calc R U . . .
C21 C 0.6738(7) 0.71309(18) 0.6412(3) 0.0816(13) Uani 1 1 d . U . . .
H21A H 0.7271 0.7342 0.7050 0.122 Uiso 1 1 calc R U . . .
H21B H 0.7628 0.6857 0.6227 0.122 Uiso 1 1 calc R U . . .
H21C H 0.5647 0.6931 0.6555 0.122 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
S001 O6 1.516(3) . ?
S001 C21 1.739(4) . ?
S001 C22 1.753(4) . ?
O12 C14 1.335(3) . ?
O12 C4 1.389(3) . ?
O3 C00H 1.339(3) . ?
O3 C17 1.451(4) . ?
O2 C00H 1.200(3) . ?
O7 C14 1.202(3) . ?
O1 C1 1.367(3) . ?
O007 C11 1.351(3) . ?
N2 C18 1.364(3) . ?
N2 C12 1.390(4) . ?
O4 N1 1.229(3) . ?
O5 N1 1.227(3) . ?
N1 C8 1.451(4) . ?
C5 C4 1.383(4) . ?
C5 C6 1.410(4) . ?
C5 C15 1.462(3) . ?
C15 C18 1.363(3) . ?
C15 C00H 1.487(4) . ?
C18 C14 1.481(4) . ?
C7 C12 1.379(4) . ?
C7 C8 1.392(4) . ?
C6 C1 1.380(4) . ?
C4 C3 1.376(4) . ?
C12 C11 1.398(4) . ?
C8 C9 1.372(4) . ?
C9 C10 1.367(4) . ?
C11 C10 1.386(4) . ?
C1 C2 1.380(4) . ?
C3 C2 1.386(4) . ?

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
O6 S001 C21 106.5(2) . . ?
O6 S001 C22 105.66(16) . . ?
C21 S001 C22 99.7(2) . . ?
C14 O12 C4 122.1(2) . . ?
C00H O3 C17 115.8(2) . . ?
C18 N2 C12 133.0(2) . . ?
O5 N1 O4 122.2(3) . . ?
O5 N1 C8 119.4(2) . . ?
O4 N1 C8 118.4(2) . . ?
C4 C5 C6 116.5(2) . . ?
C4 C5 C15 118.2(2) . . ?
C6 C5 C15 125.2(2) . . ?
C18 C15 C5 118.9(2) . . ?
C18 C15 C00H 120.1(2) . . ?
C5 C15 C00H 120.7(2) . . ?
C15 C18 N2 129.2(2) . . ?
C15 C18 C14 120.4(2) . . ?
N2 C18 C14 110.3(2) . . ?
O2 C00H O3 123.3(2) . . ?
O2 C00H C15 124.3(2) . . ?
O3 C00H C15 112.5(2) . . ?
C12 C7 C8 118.4(2) . . ?
O7 C14 O12 118.7(2) . . ?
O7 C14 C18 123.0(3) . . ?
O12 C14 C18 118.3(2) . . ?
C1 C6 C5 120.6(3) . . ?
C3 C4 C5 123.5(3) . . ?
C3 C4 O12 114.9(2) . . ?
C5 C4 O12 121.6(2) . . ?
C7 C12 N2 124.8(2) . . ?
C7 C12 C11 119.5(2) . . ?
N2 C12 C11 115.5(2) . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 N1 119.5(3) . . ?
C7 C8 N1 117.8(2) . . ?
C10 C9 C8 118.5(3) . . ?
O007 C11 C10 124.3(2) . . ?
O007 C11 C12 115.4(3) . . ?
C10 C11 C12 120.2(3) . . ?
C9 C10 C11 120.8(3) . . ?
O1 C1 C6 121.9(3) . . ?
O1 C1 C2 117.1(2) . . ?
C6 C1 C2 121.0(3) . . ?
C4 C3 C2 118.9(3) . . ?
C1 C2 C3 119.5(3) . . ?

_refine_diff_density_max         1.886
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 982194'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_DATAM_A

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N O6'
_chemical_formula_sum            'C22 H17 N O6'
_chemical_formula_weight         391.11

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                   8.447(6)
_cell_length_b                   9.631(6)
_cell_length_c                   22.349(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.54(2)
_cell_angle_gamma                90
_cell_volume                     1818(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.985
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34363
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3708
_reflns_number_gt                2558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 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         3708
_refine_ls_number_parameters     262
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1634
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
O4 O 0.06109(14) 0.29300(12) 0.65414(5) 0.0493(4) Uani 1 1 d . U . . .
O3 O 0.23035(16) 0.30340(12) 0.73310(5) 0.0555(4) Uani 1 1 d . U . . .
O1 O 0.34175(15) -0.21021(13) 0.77948(5) 0.0558(4) Uani 1 1 d . U . . .
O2 O 0.16840(17) -0.21800(13) 0.70501(6) 0.0652(4) Uani 1 1 d . U . . .
O5 O -0.37986(16) -0.06061(16) 0.64194(7) 0.0713(5) Uani 1 1 d . U . . .
H5 H -0.4292 -0.1042 0.6160 1.000 Uiso 1 1 calc R U . . .
N1 N 0.34551(17) 0.07609(14) 0.77699(6) 0.0486(4) Uani 1 1 d . U . . .
O8 O -0.28380(17) -0.19758(17) 0.54317(6) 0.0739(5) Uani 1 1 d . U . . .
H8 H -0.3710 -0.1894 0.5581 1.000 Uiso 1 1 calc R U . . .
C13 C 0.0364(2) 0.00944(16) 0.65315(7) 0.0385(4) Uani 1 1 d . U . . .
C14 C 0.0931(2) -0.05780(16) 0.59783(7) 0.0395(4) Uani 1 1 d . U . . .
C9 C 0.15259(19) 0.08033(16) 0.69506(7) 0.0387(4) Uani 1 1 d . U . . .
C15 C -0.0156(2) -0.12624(16) 0.55853(7) 0.0417(4) Uani 1 1 d . U . . .
C17 C -0.2398(2) -0.05675(18) 0.62959(8) 0.0476(5) Uani 1 1 d . U . . .
C8 C 0.2484(2) 0.01015(17) 0.73564(7) 0.0410(4) Uani 1 1 d . U . . .
C30 C -0.1196(2) 0.01237(17) 0.66609(8) 0.0447(4) Uani 1 1 d . U . . .
H30A H -0.1506 0.0608 0.6998 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1531(2) 0.23463(17) 0.69658(7) 0.0414(4) Uani 1 1 d . U . . .
C1 C 0.4230(2) 0.00670(19) 0.82431(7) 0.0459(4) Uani 1 1 d . U . . .
C2 C 0.4195(2) -0.13743(19) 0.82565(8) 0.0479(5) Uani 1 1 d . U . . .
C19 C 0.2520(2) -0.05502(18) 0.58282(8) 0.0491(5) Uani 1 1 d . U . . .
H19A H 0.3251 -0.0095 0.6077 0.059 Uiso 1 1 calc R U . . .
C16 C -0.1860(2) -0.13350(18) 0.57300(8) 0.0479(5) Uani 1 1 d . U . . .
C7 C 0.2466(2) -0.14687(18) 0.73780(8) 0.0460(4) Uani 1 1 d . U . . .
C22 C 0.0372(2) -0.18867(19) 0.50622(7) 0.0536(5) Uani 1 1 d . U . . .
H22A H -0.0348 -0.2327 0.4804 0.064 Uiso 1 1 calc R U . . .
C6 C 0.4988(2) 0.0781(2) 0.87130(8) 0.0556(5) Uani 1 1 d . U . . .
H6A H 0.5026 0.1746 0.8712 0.067 Uiso 1 1 calc R U . . .
C11 C 0.0604(3) 0.44490(17) 0.65478(9) 0.0550(5) Uani 1 1 d . U . . .
H11A H 0.1681 0.4798 0.6545 0.066 Uiso 1 1 calc R U . . .
H11B H 0.0110 0.4784 0.6907 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1958(3) -0.1853(2) 0.49274(8) 0.0601(5) Uani 1 1 d . U . . .
H21A H 0.2303 -0.2273 0.4580 0.072 Uiso 1 1 calc R U . . .
C20 C 0.3030(2) -0.1198(2) 0.53086(9) 0.0597(6) Uani 1 1 d . U . . .
H20A H 0.4099 -0.1187 0.5219 0.072 Uiso 1 1 calc R U . . .
C3 C 0.4893(2) -0.2116(2) 0.87173(8) 0.0592(5) Uani 1 1 d . U . . .
H3A H 0.4861 -0.3081 0.8717 0.071 Uiso 1 1 calc R U . . .
C4 C 0.5646(2) -0.1405(3) 0.91822(9) 0.0691(6) Uani 1 1 d . U . . .
H4A H 0.6128 -0.1893 0.9497 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5681(3) 0.0038(2) 0.91793(9) 0.0661(6) Uani 1 1 d . U . . .
H5A H 0.6177 0.0509 0.9495 0.079 Uiso 1 1 calc R U . . .
C12 C -0.0299(3) 0.4945(2) 0.60073(11) 0.0842(8) Uani 1 1 d . U . . .
H12A H -0.0317 0.5942 0.6005 0.126 Uiso 1 1 calc R U . . .
H12B H -0.1364 0.4598 0.6015 0.126 Uiso 1 1 calc R U . . .
H12C H 0.0202 0.4615 0.5654 0.126 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
O4 C10 1.334(2) . ?
O4 C11 1.463(2) . ?
O3 C10 1.226(2) . ?
O1 C7 1.358(2) . ?
O1 C2 1.397(2) . ?
O2 C7 1.190(2) . ?
O5 C17 1.223(2) . ?
N1 C8 1.374(2) . ?
N1 C1 1.399(2) . ?
O8 C16 1.216(2) . ?
C13 C30 1.357(3) . ?
C13 C14 1.486(2) . ?
C13 C9 1.502(2) . ?
C14 C19 1.393(3) . ?
C14 C15 1.416(2) . ?
C9 C8 1.377(2) . ?
C9 C10 1.486(2) . ?
C15 C22 1.398(2) . ?
C15 C16 1.486(3) . ?
C17 C30 1.447(3) . ?
C17 C16 1.544(3) . ?
C8 C7 1.513(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.373(3) . ?
C19 C20 1.396(3) . ?
C22 C21 1.381(3) . ?
C6 C5 1.381(3) . ?
C11 C12 1.490(3) . ?
C21 C20 1.380(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.390(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O4 C11 114.64(14) . . ?
C7 O1 C2 122.62(14) . . ?
C8 N1 C1 123.10(16) . . ?
C30 C13 C14 121.51(15) . . ?
C30 C13 C9 118.66(15) . . ?
C14 C13 C9 119.79(15) . . ?
C19 C14 C15 118.20(15) . . ?
C19 C14 C13 121.74(16) . . ?
C15 C14 C13 120.05(15) . . ?
C8 C9 C10 118.33(15) . . ?
C8 C9 C13 123.38(15) . . ?
C10 C9 C13 118.03(14) . . ?
C22 C15 C14 120.18(17) . . ?
C22 C15 C16 119.63(16) . . ?
C14 C15 C16 120.18(15) . . ?
O5 C17 C30 123.72(17) . . ?
O5 C17 C16 118.56(16) . . ?
C30 C17 C16 117.69(16) . . ?
N1 C8 C9 123.07(16) . . ?
N1 C8 C7 116.54(15) . . ?
C9 C8 C7 120.36(15) . . ?
C13 C30 C17 122.73(16) . . ?
O3 C10 O4 122.37(16) . . ?
O3 C10 C9 123.81(16) . . ?
O4 C10 C9 113.82(15) . . ?
C2 C1 N1 118.97(16) . . ?
C2 C1 C6 119.03(17) . . ?
N1 C1 C6 121.96(18) . . ?
C3 C2 C1 121.83(18) . . ?
C3 C2 O1 118.47(17) . . ?
C1 C2 O1 119.69(16) . . ?
C14 C19 C20 120.85(18) . . ?
O8 C16 C15 123.56(17) . . ?
O8 C16 C17 118.79(17) . . ?
C15 C16 C17 117.64(14) . . ?
O2 C7 O1 118.17(16) . . ?
O2 C7 C8 124.16(16) . . ?
O1 C7 C8 117.67(15) . . ?
C21 C22 C15 120.36(17) . . ?
C5 C6 C1 119.3(2) . . ?
O4 C11 C12 108.36(17) . . ?
C20 C21 C22 120.03(17) . . ?
C21 C20 C19 120.36(18) . . ?
C2 C3 C4 119.0(2) . . ?
C3 C4 C5 120.04(19) . . ?
C6 C5 C4 120.8(2) . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 982195'
