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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s15ab4
_database_code_depnum_ccdc_archive 'CCDC 1523960'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H22 N2 O7 S'
_chemical_formula_sum            'C18 H22 N2 O7 S'
_chemical_formula_weight         410.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.44190(10)
_cell_length_b                   14.7348(2)
_cell_length_c                   10.71760(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.3100(10)
_cell_angle_gamma                90
_cell_volume                     976.37(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10085
_cell_measurement_theta_min      4.2920
_cell_measurement_theta_max      72.4000

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.859
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_T_min  0.52689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            14552
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.298
_diffrn_reflns_theta_max         72.553
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3741
_reflns_number_gt                3658
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.966

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          
;
The hetero atom hydrogen has been found in the difference Fourier map 
and was refined freely.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0462P)²+0.0664P] 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_abs_structure_details 
;
 Flack x determined using 1642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3741
_refine_ls_number_parameters     260
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0742
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
S1 S 0.19487(8) 0.45619(4) 0.53476(5) 0.02399(14) Uani 1 1 d . . . . .
O1 O 0.0999(3) 0.46403(13) 0.39811(16) 0.0313(4) Uani 1 1 d . . . . .
O2 O 0.4193(3) 0.43405(12) 0.58531(19) 0.0337(4) Uani 1 1 d . . . . .
O3 O 0.0543(3) 0.37935(11) 0.57555(16) 0.0242(3) Uani 1 1 d . . . . .
N1 N -0.1263(3) 0.13503(13) 0.76734(18) 0.0220(4) Uani 1 1 d . . . . .
N2 N -0.3748(3) 0.02504(13) 0.7892(2) 0.0249(4) Uani 1 1 d . . . . .
O4 O 0.3651(3) 0.26685(12) 0.96384(16) 0.0283(4) Uani 1 1 d . . . . .
H4A H 0.354(5) 0.321(3) 0.988(3) 0.039(9) Uiso 1 1 d . . . . .
O5 O 0.1718(2) 0.18839(11) 0.70705(16) 0.0230(3) Uani 1 1 d . . . . .
O6 O -0.4405(2) 0.11456(12) 0.60790(17) 0.0274(4) Uani 1 1 d . . . . .
O7 O -0.3116(3) -0.06035(13) 0.97324(19) 0.0385(4) Uani 1 1 d . . . . .
C1 C 0.0045(8) 0.7859(2) 0.8191(4) 0.0596(10) Uani 1 1 d . . . . .
H1A H -0.0455 0.8367 0.7592 0.089 Uiso 1 1 calc R U . . .
H1B H 0.1358 0.8036 0.8862 0.089 Uiso 1 1 calc R U . . .
H1C H -0.1085 0.7694 0.8600 0.089 Uiso 1 1 calc R U . . .
C2 C 0.0532(6) 0.70552(19) 0.7447(3) 0.0414(7) Uani 1 1 d . . . . .
C3 C -0.1084(5) 0.6663(2) 0.6450(3) 0.0373(6) Uani 1 1 d . . . . .
H3 H -0.2493 0.6921 0.6213 0.045 Uiso 1 1 calc R U . . .
C4 C -0.0671(4) 0.59041(18) 0.5796(2) 0.0310(5) Uani 1 1 d . . . . .
H4 H -0.1784 0.5642 0.5114 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1392(4) 0.55302(17) 0.6150(2) 0.0255(5) Uani 1 1 d . . . . .
C6 C 0.3035(5) 0.5918(2) 0.7122(3) 0.0409(6) Uani 1 1 d . . . . .
H6 H 0.4451 0.5668 0.7342 0.049 Uiso 1 1 calc R U . . .
C7 C 0.2593(5) 0.6678(2) 0.7773(3) 0.0471(8) Uani 1 1 d . . . . .
H7 H 0.3712 0.6943 0.8448 0.057 Uiso 1 1 calc R U . . .
C8 C 0.1244(3) 0.34785(15) 0.7106(2) 0.0202(4) Uani 1 1 d . . . . .
H8 H 0.1789 0.3989 0.7726 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2921(4) 0.27194(15) 0.7263(2) 0.0222(5) Uani 1 1 d . . . . .
H9 H 0.3680 0.2782 0.6572 0.027 Uiso 1 1 calc R U . . .
C10 C 0.4580(4) 0.27204(17) 0.8584(2) 0.0268(5) Uani 1 1 d . . . . .
H10A H 0.5568 0.2199 0.8633 0.032 Uiso 1 1 calc R U . . .
H10B H 0.5454 0.3282 0.8672 0.032 Uiso 1 1 calc R U . . .
C11 C -0.0687(4) 0.30126(15) 0.7365(2) 0.0234(5) Uani 1 1 d . . . . .
H11A H -0.2058 0.3301 0.6867 0.028 Uiso 1 1 calc R U . . .
H11B H -0.0598 0.3026 0.8302 0.028 Uiso 1 1 calc R U . . .
C12 C -0.0517(4) 0.20436(15) 0.6902(2) 0.0215(4) Uani 1 1 d . . . . .
H12 H -0.1334 0.1985 0.5963 0.026 Uiso 1 1 calc R U . . .
C13 C -0.3217(4) 0.09322(15) 0.7129(2) 0.0221(4) Uani 1 1 d . . . . .
C14 C -0.5804(4) -0.02199(19) 0.7310(3) 0.0387(7) Uani 1 1 d . . . . .
H14A H -0.7003 0.0211 0.7188 0.058 Uiso 1 1 calc R U . . .
H14B H -0.5986 -0.0711 0.7888 0.058 Uiso 1 1 calc R U . . .
H14C H -0.5796 -0.0474 0.6467 0.058 Uiso 1 1 calc R U . . .
C15 C -0.2487(4) -0.00142(16) 0.9107(2) 0.0270(5) Uani 1 1 d . . . . .
C16 C -0.0428(4) 0.04431(17) 0.9588(2) 0.0285(5) Uani 1 1 d . . . . .
C17 C 0.1078(5) 0.0146(2) 1.0856(3) 0.0439(7) Uani 1 1 d . . . . .
H17A H 0.1552 -0.0478 1.0776 0.066 Uiso 1 1 calc R U . . .
H17B H 0.0329 0.0173 1.1534 0.066 Uiso 1 1 calc R U . . .
H17C H 0.2339 0.0549 1.1087 0.066 Uiso 1 1 calc R U . . .
C18 C 0.0077(4) 0.11012(17) 0.8862(2) 0.0265(5) Uani 1 1 d . . . . .
H18 H 0.1419 0.1408 0.9182 0.032 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
S1 O1 1.4246(17) . ?
S1 O2 1.4318(18) . ?
S1 O3 1.5859(16) . ?
S1 C5 1.754(3) . ?
O3 C8 1.465(3) . ?
N1 C18 1.373(3) . ?
N1 C13 1.376(3) . ?
N1 C12 1.477(3) . ?
N2 C15 1.384(3) . ?
N2 C13 1.397(3) . ?
N2 C14 1.470(3) . ?
O4 C10 1.422(3) . ?
O4 H4A 0.85(4) . ?
O5 C12 1.419(3) . ?
O5 C9 1.438(3) . ?
O6 C13 1.211(3) . ?
O7 C15 1.233(3) . ?
C1 C2 1.508(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.390(5) . ?
C2 C3 1.391(4) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C11 1.514(3) . ?
C8 C9 1.531(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.515(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.447(3) . ?
C16 C18 1.340(3) . ?
C16 C17 1.496(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.27(11) . . ?
O1 S1 O3 103.16(10) . . ?
O2 S1 O3 109.09(10) . . ?
O1 S1 C5 110.51(12) . . ?
O2 S1 C5 108.87(12) . . ?
O3 S1 C5 103.56(10) . . ?
C8 O3 S1 117.19(13) . . ?
C18 N1 C13 122.42(19) . . ?
C18 N1 C12 119.05(19) . . ?
C13 N1 C12 118.37(18) . . ?
C15 N2 C13 125.3(2) . . ?
C15 N2 C14 119.2(2) . . ?
C13 N2 C14 115.5(2) . . ?
C10 O4 H4A 107(2) . . ?
C12 O5 C9 111.26(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.9(3) . . ?
C7 C2 C1 120.4(3) . . ?
C3 C2 C1 120.7(3) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 S1 119.1(2) . . ?
C4 C5 S1 120.0(2) . . ?
C5 C6 C7 119.3(3) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O3 C8 C11 106.50(17) . . ?
O3 C8 C9 110.66(17) . . ?
C11 C8 C9 103.84(18) . . ?
O3 C8 H8 111.8 . . ?
C11 C8 H8 111.8 . . ?
C9 C8 H8 111.8 . . ?
O5 C9 C10 110.20(19) . . ?
O5 C9 C8 105.94(17) . . ?
C10 C9 C8 113.15(18) . . ?
O5 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
C8 C9 H9 109.2 . . ?
O4 C10 C9 113.47(19) . . ?
O4 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
O4 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C8 C11 C12 103.08(17) . . ?
C8 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C8 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
O5 C12 N1 106.98(17) . . ?
O5 C12 C11 106.08(18) . . ?
N1 C12 C11 113.60(18) . . ?
O5 C12 H12 110.0 . . ?
N1 C12 H12 110.0 . . ?
C11 C12 H12 110.0 . . ?
O6 C13 N1 122.8(2) . . ?
O6 C13 N2 122.4(2) . . ?
N1 C13 N2 114.8(2) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O7 C15 N2 121.0(2) . . ?
O7 C15 C16 122.9(2) . . ?
N2 C15 C16 116.2(2) . . ?
C18 C16 C15 118.5(2) . . ?
C18 C16 C17 122.5(2) . . ?
C15 C16 C17 118.9(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 N1 122.7(2) . . ?
C16 C18 H18 118.6 . . ?
N1 C18 H18 118.6 . . ?

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
O1 S1 O3 C8 174.01(15) . . . . ?
O2 S1 O3 C8 45.06(18) . . . . ?
C5 S1 O3 C8 -70.75(17) . . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C4 -177.5(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C3 C4 C5 S1 179.4(2) . . . . ?
O1 S1 C5 C6 -135.8(2) . . . . ?
O2 S1 C5 C6 -1.7(2) . . . . ?
O3 S1 C5 C6 114.3(2) . . . . ?
O1 S1 C5 C4 43.3(2) . . . . ?
O2 S1 C5 C4 177.49(19) . . . . ?
O3 S1 C5 C4 -66.5(2) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
S1 C5 C6 C7 -179.1(2) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
C1 C2 C7 C6 177.7(3) . . . . ?
C5 C6 C7 C2 -0.7(5) . . . . ?
S1 O3 C8 C11 161.13(14) . . . . ?
S1 O3 C8 C9 -86.64(19) . . . . ?
C12 O5 C9 C10 118.54(19) . . . . ?
C12 O5 C9 C8 -4.2(2) . . . . ?
O3 C8 C9 O5 -91.8(2) . . . . ?
C11 C8 C9 O5 22.1(2) . . . . ?
O3 C8 C9 C10 147.36(18) . . . . ?
C11 C8 C9 C10 -98.7(2) . . . . ?
O5 C9 C10 O4 -62.3(2) . . . . ?
C8 C9 C10 O4 56.1(3) . . . . ?
O3 C8 C11 C12 86.4(2) . . . . ?
C9 C8 C11 C12 -30.5(2) . . . . ?
C9 O5 C12 N1 -137.06(18) . . . . ?
C9 O5 C12 C11 -15.5(2) . . . . ?
C18 N1 C12 O5 38.4(3) . . . . ?
C13 N1 C12 O5 -137.02(19) . . . . ?
C18 N1 C12 C11 -78.3(3) . . . . ?
C13 N1 C12 C11 106.3(2) . . . . ?
C8 C11 C12 O5 28.7(2) . . . . ?
C8 C11 C12 N1 145.95(18) . . . . ?
C18 N1 C13 O6 -179.7(2) . . . . ?
C12 N1 C13 O6 -4.5(3) . . . . ?
C18 N1 C13 N2 1.4(3) . . . . ?
C12 N1 C13 N2 176.59(18) . . . . ?
C15 N2 C13 O6 -178.7(2) . . . . ?
C14 N2 C13 O6 2.6(3) . . . . ?
C15 N2 C13 N1 0.3(3) . . . . ?
C14 N2 C13 N1 -178.5(2) . . . . ?
C13 N2 C15 O7 177.5(2) . . . . ?
C14 N2 C15 O7 -3.8(4) . . . . ?
C13 N2 C15 C16 -2.1(3) . . . . ?
C14 N2 C15 C16 176.6(2) . . . . ?
O7 C15 C16 C18 -177.3(2) . . . . ?
N2 C15 C16 C18 2.3(3) . . . . ?
O7 C15 C16 C17 4.5(4) . . . . ?
N2 C15 C16 C17 -175.9(2) . . . . ?
C15 C16 C18 N1 -0.9(4) . . . . ?
C17 C16 C18 N1 177.3(3) . . . . ?
C13 N1 C18 C16 -1.0(4) . . . . ?
C12 N1 C18 C16 -176.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O7 0.85(4) 1.83(4) 2.681(3) 175(3) 2_557

_refine_diff_density_max         0.135
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_s15ab6a
_database_code_depnum_ccdc_archive 'CCDC 1523961'
_audit_update_record             
;
2016-12-21 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O6'
_chemical_formula_sum            'C12 H14 N2 O6'
_chemical_formula_weight         282.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.0627(2)
_cell_length_b                   9.6573(4)
_cell_length_c                   10.0320(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.448(4)
_cell_angle_gamma                90
_cell_volume                     641.13(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3370
_cell_measurement_theta_min      4.7020
_cell_measurement_theta_max      71.9870

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.016
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_T_min  0.78559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_reflns_number            5532
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.572
_diffrn_reflns_theta_max         72.400
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_full 0.865
_reflns_number_total             2172
_reflns_number_gt                2076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.625
_reflns_Friedel_fraction_max     0.699
_reflns_Friedel_fraction_full    0.716

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_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)+(0.0444P)²+0.0470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2172
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0779
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6373(3) 0.5499(3) 0.6252(3) 0.0351(6) Uani 1 1 d . . . . .
C2 C 0.3242(3) 0.4580(3) 0.6475(2) 0.0249(5) Uani 1 1 d . . . . .
H2 H 0.3366 0.4158 0.7412 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1593(3) 0.3894(3) 0.5259(2) 0.0248(5) Uani 1 1 d . . . . .
H3A H 0.0498 0.3543 0.5570 0.030 Uiso 1 1 calc R U . . .
H3B H 0.2137 0.3118 0.4856 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0842(3) 0.5069(3) 0.4180(2) 0.0249(5) Uani 1 1 d . . . . .
H4 H -0.0667 0.5109 0.3847 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2544(3) 0.6049(3) 0.6373(2) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.1499 0.6147 0.6829 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4232(4) 0.7042(3) 0.7038(3) 0.0351(6) Uani 1 1 d . . . . .
H6A H 0.3754 0.7997 0.6745 0.042 Uiso 1 1 calc R U . . .
H6B H 0.4639 0.6987 0.8086 0.042 Uiso 1 1 calc R U . . .
C7 C 0.0401(3) 0.4029(3) 0.1893(2) 0.0283(5) Uani 1 1 d . . . . .
C8 C -0.0135(6) 0.2962(4) -0.0402(3) 0.0544(9) Uani 1 1 d . . . . .
H8A H -0.1561 0.2999 -0.0491 0.082 Uiso 1 1 calc R U . . .
H8B H 0.0370 0.2015 -0.0172 0.082 Uiso 1 1 calc R U . . .
H8C H 0.0000 0.3246 -0.1302 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2712(4) 0.4557(3) 0.0596(2) 0.0291(5) Uani 1 1 d . . . . .
C10 C 0.3807(3) 0.5475(3) 0.1746(2) 0.0246(5) Uani 1 1 d . . . . .
C11 C 0.5590(4) 0.6230(3) 0.1624(3) 0.0336(6) Uani 1 1 d . . . . .
H11A H 0.6457 0.5578 0.1356 0.050 Uiso 1 1 calc R U . . .
H11B H 0.6358 0.6656 0.2541 0.050 Uiso 1 1 calc R U . . .
H11C H 0.5121 0.6952 0.0896 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3159(3) 0.5636(2) 0.2845(2) 0.0222(4) Uani 1 1 d . . . . .
H12 H 0.3869 0.6250 0.3592 0.027 Uiso 1 1 calc R U . . .
N1 N 0.1497(3) 0.4940(2) 0.29270(18) 0.0239(4) Uani 1 1 d . . . . .
N2 N 0.1040(3) 0.3899(2) 0.0734(2) 0.0322(5) Uani 1 1 d . . . . .
O1 O 0.7849(3) 0.5331(3) 0.5936(3) 0.0559(6) Uani 1 1 d . . . . .
O2 O 0.5126(2) 0.4453(2) 0.61781(19) 0.0340(4) Uani 1 1 d . . . . .
O3 O 0.5976(3) 0.6753(2) 0.6627(2) 0.0408(5) Uani 1 1 d . . . . .
O4 O 0.1647(2) 0.63166(18) 0.48712(16) 0.0277(4) Uani 1 1 d . . . . .
O5 O -0.1034(3) 0.3384(2) 0.19854(19) 0.0375(4) Uani 1 1 d . . . . .
O6 O 0.3186(3) 0.4344(2) -0.04480(18) 0.0449(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.202(3) . ?
C1 O2 1.326(3) . ?
C1 O3 1.326(4) . ?
C2 O2 1.466(2) . ?
C2 C5 1.494(4) . ?
C2 C3 1.514(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O4 1.407(3) . ?
C4 N1 1.489(3) . ?
C4 H4 1.0000 . ?
C5 O4 1.439(3) . ?
C5 C6 1.493(3) . ?
C5 H5 1.0000 . ?
C6 O3 1.456(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O5 1.221(3) . ?
C7 N1 1.374(3) . ?
C7 N2 1.392(3) . ?
C8 N2 1.464(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O6 1.224(3) . ?
C9 N2 1.390(3) . ?
C9 C10 1.446(3) . ?
C10 C12 1.342(3) . ?
C10 C11 1.497(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.380(3) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 120.2(3) . . ?
O1 C1 O3 119.2(3) . . ?
O2 C1 O3 120.6(2) . . ?
O2 C2 C5 111.52(18) . . ?
O2 C2 C3 107.26(17) . . ?
C5 C2 C3 102.58(18) . . ?
O2 C2 H2 111.7 . . ?
C5 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
C2 C3 C4 102.98(19) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O4 C4 N1 107.26(17) . . ?
O4 C4 C3 107.82(17) . . ?
N1 C4 C3 113.68(18) . . ?
O4 C4 H4 109.3 . . ?
N1 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
O4 C5 C6 110.1(2) . . ?
O4 C5 C2 104.84(17) . . ?
C6 C5 C2 112.7(2) . . ?
O4 C5 H5 109.7 . . ?
C6 C5 H5 109.7 . . ?
C2 C5 H5 109.7 . . ?
O3 C6 C5 111.9(2) . . ?
O3 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
O3 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O5 C7 N1 122.2(2) . . ?
O5 C7 N2 122.5(2) . . ?
N1 C7 N2 115.3(2) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C9 N2 120.3(2) . . ?
O6 C9 C10 123.8(2) . . ?
N2 C9 C10 115.91(19) . . ?
C12 C10 C9 119.1(2) . . ?
C12 C10 C11 123.3(2) . . ?
C9 C10 C11 117.6(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 N1 122.2(2) . . ?
C10 C12 H12 118.9 . . ?
N1 C12 H12 118.9 . . ?
C7 N1 C12 122.26(18) . . ?
C7 N1 C4 115.58(18) . . ?
C12 N1 C4 122.09(17) . . ?
C9 N2 C7 125.2(2) . . ?
C9 N2 C8 118.4(2) . . ?
C7 N2 C8 116.4(2) . . ?
C1 O2 C2 123.9(2) . . ?
C1 O3 C6 122.6(2) . . ?
C4 O4 C5 108.47(18) . . ?

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
O2 C2 C3 C4 -88.0(2) . . . . ?
C5 C2 C3 C4 29.61(19) . . . . ?
C2 C3 C4 O4 -12.6(2) . . . . ?
C2 C3 C4 N1 106.17(19) . . . . ?
O2 C2 C5 O4 77.6(2) . . . . ?
C3 C2 C5 O4 -36.87(19) . . . . ?
O2 C2 C5 C6 -42.1(2) . . . . ?
C3 C2 C5 C6 -156.61(18) . . . . ?
O4 C5 C6 O3 -71.1(3) . . . . ?
C2 C5 C6 O3 45.6(3) . . . . ?
O6 C9 C10 C12 -180.0(3) . . . . ?
N2 C9 C10 C12 -0.2(3) . . . . ?
O6 C9 C10 C11 1.6(4) . . . . ?
N2 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C12 N1 1.0(3) . . . . ?
C11 C10 C12 N1 179.2(2) . . . . ?
O5 C7 N1 C12 177.9(2) . . . . ?
N2 C7 N1 C12 -2.3(3) . . . . ?
O5 C7 N1 C4 1.0(3) . . . . ?
N2 C7 N1 C4 -179.2(2) . . . . ?
C10 C12 N1 C7 0.4(3) . . . . ?
C10 C12 N1 C4 177.0(2) . . . . ?
O4 C4 N1 C7 -161.33(19) . . . . ?
C3 C4 N1 C7 79.6(2) . . . . ?
O4 C4 N1 C12 21.8(3) . . . . ?
C3 C4 N1 C12 -97.3(2) . . . . ?
O6 C9 N2 C7 177.8(2) . . . . ?
C10 C9 N2 C7 -2.0(4) . . . . ?
O6 C9 N2 C8 -0.5(4) . . . . ?
C10 C9 N2 C8 179.7(3) . . . . ?
O5 C7 N2 C9 -177.0(2) . . . . ?
N1 C7 N2 C9 3.2(4) . . . . ?
O5 C7 N2 C8 1.4(4) . . . . ?
N1 C7 N2 C8 -178.5(3) . . . . ?
O1 C1 O2 C2 -176.9(2) . . . . ?
O3 C1 O2 C2 0.8(3) . . . . ?
C5 C2 O2 C1 19.6(3) . . . . ?
C3 C2 O2 C1 131.2(2) . . . . ?
O1 C1 O3 C6 -179.4(2) . . . . ?
O2 C1 O3 C6 2.9(4) . . . . ?
C5 C6 O3 C1 -26.6(4) . . . . ?
N1 C4 O4 C5 -133.35(17) . . . . ?
C3 C4 O4 C5 -10.5(2) . . . . ?
C6 C5 O4 C4 151.54(19) . . . . ?
C2 C5 O4 C4 30.0(2) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037

