# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mn111045a
_database_code_depnum_ccdc_archive 'CCDC 1832969'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

_audit_creation_date             2016-02-18T13:57:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H13 N O5 S'
_chemical_formula_sum            'C13 H13 N O5 S'
_chemical_formula_weight         295.3
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.9869(2)
_cell_length_b                   11.7644(5)
_cell_length_c                   22.1329(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1298.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      28.91
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.978

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_number            29132
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2649
_reflns_number_gt                2479
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_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, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0406P)²+0.1864P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2649
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.0248
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
S1 S 0.65649(8) 1.00493(4) 0.886257(17) 0.01574(11) Uani 1 1 d . . .
O1 O 0.7549(3) 0.66608(11) 0.75788(6) 0.0225(3) Uani 1 1 d . . .
O2 O 0.7339(2) 0.95596(10) 0.71141(5) 0.0163(3) Uani 1 1 d . . .
O3 O 0.5968(2) 0.68107(10) 0.85376(5) 0.0170(3) Uani 1 1 d . . .
O4 O 0.5423(3) 0.73260(10) 0.95086(5) 0.0188(3) Uani 1 1 d . . .
O5 O 0.4082(2) 0.89496(10) 0.77346(5) 0.0182(3) Uani 1 1 d . . .
N1 N 0.9695(3) 0.77434(12) 0.83031(6) 0.0163(3) Uani 1 1 d . . .
H2 H 1.0991 0.8044 0.8086 0.02 Uiso 1 1 calc R . .
C1 C 0.7834(4) 0.70516(14) 0.80732(8) 0.0163(4) Uani 1 1 d . . .
C2 C 0.9374(3) 0.79514(14) 0.89441(7) 0.0152(4) Uani 1 1 d . . .
H13 H 1.0829 0.7549 0.917 0.018 Uiso 1 1 calc R . .
C3 C 0.9328(4) 0.91944(15) 0.91339(7) 0.0168(4) Uani 1 1 d . . .
H12 H 1.1017 0.9552 0.8996 0.02 Uiso 1 1 calc R . .
H11 H 0.9321 0.9224 0.9581 0.02 Uiso 1 1 calc R . .
C4 C 0.7409(4) 1.03094(14) 0.80825(7) 0.0160(4) Uani 1 1 d . . .
H3 H 0.691 1.1101 0.798 0.019 Uiso 1 1 calc R . .
H10 H 0.9376 1.024 0.8035 0.019 Uiso 1 1 calc R . .
C5 C 0.6063(3) 0.95176(14) 0.76397(7) 0.0139(3) Uani 1 1 d . . .
C6 C 0.6167(4) 0.88996(15) 0.66180(7) 0.0174(4) Uani 1 1 d . . .
H4 H 0.4477 0.9254 0.6478 0.021 Uiso 1 1 calc R . .
H9 H 0.5781 0.8113 0.6751 0.021 Uiso 1 1 calc R . .
C7 C 0.8219(3) 0.89014(14) 0.61218(7) 0.0145(3) Uani 1 1 d . . .
C8 C 0.8643(3) 0.98816(14) 0.57826(7) 0.0159(3) Uani 1 1 d . . .
H8 H 0.7588 1.054 0.5856 0.019 Uiso 1 1 calc R . .
C9 C 1.0605(4) 0.99000(15) 0.53365(7) 0.0163(3) Uani 1 1 d . . .
H7 H 1.0905 1.0573 0.5109 0.02 Uiso 1 1 calc R . .
C10 C 1.2120(4) 0.89396(15) 0.52229(8) 0.0162(4) Uani 1 1 d . . .
H1 H 1.3448 0.8952 0.4915 0.019 Uiso 1 1 calc R . .
C11 C 0.6734(4) 0.73573(14) 0.90588(7) 0.0150(4) Uani 1 1 d . . .
C12 C 1.1708(4) 0.79611(15) 0.55557(8) 0.0183(4) Uani 1 1 d . . .
H6 H 1.2753 0.7302 0.5477 0.022 Uiso 1 1 calc R . .
C13 C 0.9757(4) 0.79426(14) 0.60066(7) 0.0161(4) Uani 1 1 d . . .
H5 H 0.9479 0.7271 0.6236 0.019 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C4 1.8033(16) . ?
S1 C3 1.8084(19) . ?
O1 C1 1.195(2) . ?
O2 C5 1.3271(19) . ?
O2 C6 1.466(2) . ?
O3 C11 1.375(2) . ?
O3 C1 1.415(2) . ?
O4 C11 1.192(2) . ?
O5 C5 1.211(2) . ?
N1 C1 1.335(2) . ?
N1 C2 1.449(2) . ?
N1 H2 0.88 . ?
C2 C11 1.512(2) . ?
C2 C3 1.522(2) . ?
C2 H13 1 . ?
C3 H12 0.99 . ?
C3 H11 0.99 . ?
C4 C5 1.510(2) . ?
C4 H3 0.99 . ?
C4 H10 0.99 . ?
C6 C7 1.501(2) . ?
C6 H4 0.99 . ?
C6 H9 0.99 . ?
C7 C13 1.388(2) . ?
C7 C8 1.392(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.95 . ?
C9 C10 1.382(3) . ?
C9 H7 0.95 . ?
C10 C12 1.382(2) . ?
C10 H1 0.95 . ?
C12 C13 1.394(3) . ?
C12 H6 0.95 . ?
C13 H5 0.95 . ?

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 S1 C3 103.56(9) . . ?
C5 O2 C6 116.46(13) . . ?
C11 O3 C1 109.47(13) . . ?
C1 N1 C2 113.55(14) . . ?
C1 N1 H2 123.2 . . ?
C2 N1 H2 123.2 . . ?
O1 C1 N1 131.75(17) . . ?
O1 C1 O3 120.64(17) . . ?
N1 C1 O3 107.60(14) . . ?
N1 C2 C11 100.51(14) . . ?
N1 C2 C3 115.75(14) . . ?
C11 C2 C3 112.61(14) . . ?
N1 C2 H13 109.2 . . ?
C11 C2 H13 109.2 . . ?
C3 C2 H13 109.2 . . ?
C2 C3 S1 117.03(12) . . ?
C2 C3 H12 108 . . ?
S1 C3 H12 108 . . ?
C2 C3 H11 108 . . ?
S1 C3 H11 108 . . ?
H12 C3 H11 107.3 . . ?
C5 C4 S1 114.39(12) . . ?
C5 C4 H3 108.7 . . ?
S1 C4 H3 108.7 . . ?
C5 C4 H10 108.7 . . ?
S1 C4 H10 108.7 . . ?
H3 C4 H10 107.6 . . ?
O5 C5 O2 124.33(15) . . ?
O5 C5 C4 126.20(15) . . ?
O2 C5 C4 109.44(14) . . ?
O2 C6 C7 106.00(13) . . ?
O2 C6 H4 110.5 . . ?
C7 C6 H4 110.5 . . ?
O2 C6 H9 110.5 . . ?
C7 C6 H9 110.5 . . ?
H4 C6 H9 108.7 . . ?
C13 C7 C8 119.36(15) . . ?
C13 C7 C6 120.67(15) . . ?
C8 C7 C6 119.95(15) . . ?
C9 C8 C7 120.19(16) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.08(16) . . ?
C10 C9 H7 120 . . ?
C8 C9 H7 120 . . ?
C12 C10 C9 120.18(16) . . ?
C12 C10 H1 119.9 . . ?
C9 C10 H1 119.9 . . ?
O4 C11 O3 122.29(16) . . ?
O4 C11 C2 129.23(16) . . ?
O3 C11 C2 108.48(14) . . ?
C10 C12 C13 119.89(16) . . ?
C10 C12 H6 120.1 . . ?
C13 C12 H6 120.1 . . ?
C7 C13 C12 120.31(15) . . ?
C7 C13 H5 119.8 . . ?
C12 C13 H5 119.8 . . ?

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
N1 H2 O5 0.88 2.03 2.8956(19) 168.2 1_655
C2 H13 O4 1 2.42 3.347(2) 153 1_655
C4 H3 O1 0.99 2.63 3.284(2) 123.8 3_656
C4 H10 O1 0.99 2.64 3.315(2) 125.3 3_756

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
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# END of CIF
