# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1494932'
_audit_update_record             
;
2016-07-20 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.2425(11)
_cell_length_b                   8.4394(10)
_cell_length_c                   13.236(2)
_cell_angle_alpha                90.149(11)
_cell_angle_beta                 100.435(12)
_cell_angle_gamma                104.134(11)
_cell_volume                     877.0(2)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C8 H10 N2 O1 S1'
_chemical_formula_moiety         'C8 H10 N2 O1 S1'
_chemical_compound_source        ?
_chemical_formula_weight         182.25


_cell_measurement_reflns_used    5724
_cell_measurement_theta_min      5
_cell_measurement_theta_max      71
_cell_measurement_temperature    180

_exptl_crystal_description       planar
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.220

_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    2.894

# Sheldrick geometric approximatio 0.59 0.79 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.79
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      180
_diffrn_reflns_number            12822
_reflns_number_total             3331
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3331 
# Theoretical number of reflections is about 6705 


_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         70.466
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        69.057
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.25


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_number_parameters     217
_oxford_refine_ls_R_factor_ref   0.0340
_refine_ls_wR_factor_ref         0.0425
_refine_ls_goodness_of_fit_ref   1.0588
_refine_ls_shift/su_max          0.0012226
_refine_ls_shift/su_mean         0.0000493


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3317
_refine_ls_R_factor_all          0.0417
_refine_ls_wR_factor_all         0.0428

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2868
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_gt          0.0425

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 11.3 -0.914 9.69 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 1.4056(2) 0.7216(2) 0.51910(12) 0.0471 1.0000 Uani . . . . . .
C2 C 1.5164(2) 0.6695(2) 0.59039(14) 0.0376 1.0000 Uani . . . . . .
C3 C 1.4666(2) 0.58143(19) 0.67309(13) 0.0328 1.0000 Uani . . . . . .
C4 C 1.2964(2) 0.54474(19) 0.68445(13) 0.0303 1.0000 Uani . . . . . .
C5 C 1.1824(2) 0.6015(2) 0.61100(15) 0.0396 1.0000 Uani . . . . . .
C6 C 1.2430(3) 0.6872(2) 0.53086(16) 0.0482 1.0000 Uani . . . . . .
C7 C 1.23884(19) 0.44741(18) 0.76964(13) 0.0285 1.0000 Uani . . . . . .
S8 S 1.03543(5) 0.33844(5) 0.75391(3) 0.0355 1.0000 Uani . . . . . .
O9 O 1.01814(15) 0.25476(15) 0.85495(10) 0.0398 1.0000 Uani . . . . . .
N10 N 1.34351(17) 0.44043(17) 0.85614(11) 0.0326 1.0000 Uani . . . . . .
C11 C 1.6996(3) 0.7124(3) 0.57608(17) 0.0501 1.0000 Uani . . . . . .
C12 C 1.7766(3) 0.8957(3) 0.58380(17) 0.0531 1.0000 Uani . . . . . .
N21 N 0.46902(16) -0.09063(17) 0.86163(11) 0.0316 1.0000 Uani . . . . . .
C22 C 0.35980(19) -0.0284(2) 0.79415(13) 0.0305 1.0000 Uani . . . . . .
C23 C 0.18838(19) -0.05550(19) 0.80109(12) 0.0292 1.0000 Uani . . . . . .
C24 C 0.12645(18) -0.15023(18) 0.87833(12) 0.0263 1.0000 Uani . . . . . .
C25 C 0.2402(2) -0.21161(19) 0.94913(13) 0.0305 1.0000 Uani . . . . . .
C26 C 0.4086(2) -0.17789(19) 0.93652(14) 0.0323 1.0000 Uani . . . . . .
C27 C -0.05623(18) -0.18744(19) 0.88610(11) 0.0265 1.0000 Uani . . . . . .
S28 S -0.14470(4) -0.38218(4) 0.90636(3) 0.0304 1.0000 Uani . . . . . .
O29 O -0.32418(13) -0.38727(14) 0.92550(9) 0.0348 1.0000 Uani . . . . . .
N30 N -0.14107(16) -0.07281(16) 0.87777(11) 0.0306 1.0000 Uani . . . . . .
C31 C 0.4292(2) 0.0716(2) 0.71017(14) 0.0399 1.0000 Uani . . . . . .
H31 H 1.5472 0.5452 0.7211 0.0409 1.0000 Uiso R . . . . .
C32 C 0.5930(2) 0.1997(2) 0.74814(15) 0.0400 1.0000 Uani . . . . . .
H51 H 1.0671 0.5838 0.6180 0.0489 1.0000 Uiso R . . . . .
H61 H 1.1648 0.7255 0.4823 0.0592 1.0000 Uiso R . . . . .
H101 H 1.4478 0.5014 0.8693 0.0407 1.0000 Uiso R . . . . .
H102 H 1.3080 0.3889 0.9102 0.0421 1.0000 Uiso R . . . . .
H111 H 1.7657 0.6622 0.6278 0.0624 1.0000 Uiso R . . . . .
H112 H 1.7057 0.6695 0.5099 0.0609 1.0000 Uiso R . . . . .
H121 H 1.7783 0.9407 0.6511 0.0811 1.0000 Uiso R . . . . .
H122 H 1.7087 0.9454 0.5322 0.0805 1.0000 Uiso R . . . . .
H123 H 1.8907 0.9175 0.5711 0.0794 1.0000 Uiso R . . . . .
H231 H 0.1166 -0.0098 0.7538 0.0367 1.0000 Uiso R . . . . .
H251 H 0.2067 -0.2707 1.0036 0.0374 1.0000 Uiso R . . . . .
H261 H 0.4867 -0.2201 0.9833 0.0400 1.0000 Uiso R . . . . .
H301 H -0.0892 0.0303 0.8726 0.0395 1.0000 Uiso R . . . . .
H302 H -0.2502 -0.0975 0.8778 0.0370 1.0000 Uiso R . . . . .
H311 H 0.3457 0.1267 0.6759 0.0498 1.0000 Uiso R . . . . .
H312 H 0.4483 -0.0024 0.6628 0.0499 1.0000 Uiso R . . . . .
H321 H 0.6790 0.1477 0.7777 0.0612 1.0000 Uiso R . . . . .
H322 H 0.6252 0.2629 0.6910 0.0601 1.0000 Uiso R . . . . .
H323 H 0.5761 0.2727 0.7989 0.0609 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.343(3) yes
N1 . C6 . 1.338(3) yes
C2 . C3 . 1.392(2) yes
C2 . C11 . 1.511(3) yes
C3 . C4 . 1.397(2) yes
C3 . H31 . 0.941 no
C4 . C5 . 1.396(2) yes
C4 . C7 . 1.476(2) yes
C5 . C6 . 1.385(3) yes
C5 . H51 . 0.946 no
C6 . H61 . 0.941 no
C7 . S8 . 1.6792(15) yes
C7 . N10 . 1.314(2) yes
S8 . O9 . 1.5272(13) yes
N10 . H101 . 0.873 no
N10 . H102 . 0.895 no
C11 . C12 . 1.517(3) yes
C11 . H111 . 0.962 no
C11 . H112 . 0.961 no
C12 . H121 . 0.964 no
C12 . H122 . 0.966 no
C12 . H123 . 0.959 no
N21 . C22 . 1.351(2) yes
N21 . C26 . 1.333(2) yes
C22 . C23 . 1.395(2) yes
C22 . C31 . 1.508(2) yes
C23 . C24 . 1.392(2) yes
C23 . H231 . 0.932 no
C24 . C25 . 1.395(2) yes
C24 . C27 . 1.4839(19) yes
C25 . C26 . 1.389(2) yes
C25 . H251 . 0.922 no
C26 . H261 . 0.945 no
C27 . S28 . 1.6711(15) yes
C27 . N30 . 1.319(2) yes
S28 . O29 . 1.5360(11) yes
N30 . H301 . 0.879 no
N30 . H302 . 0.873 no
C31 . C32 . 1.511(2) yes
C31 . H311 . 0.970 no
C31 . H312 . 0.943 no
C32 . H321 . 0.949 no
C32 . H322 . 0.966 no
C32 . H323 . 0.962 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 117.31(16) yes
N1 . C2 . C3 . 122.27(17) yes
N1 . C2 . C11 . 116.14(17) yes
C3 . C2 . C11 . 121.59(17) yes
C2 . C3 . C4 . 120.14(16) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 117.30(16) yes
C3 . C4 . C7 . 121.34(15) yes
C5 . C4 . C7 . 121.35(15) yes
C4 . C5 . C6 . 118.61(17) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 121.6 no
C5 . C6 . N1 . 124.35(18) yes
C5 . C6 . H61 . 117.6 no
N1 . C6 . H61 . 118.1 no
C4 . C7 . S8 . 118.94(12) yes
C4 . C7 . N10 . 121.78(14) yes
S8 . C7 . N10 . 119.25(12) yes
C7 . S8 . O9 . 105.67(8) yes
C7 . N10 . H101 . 122.0 no
C7 . N10 . H102 . 122.4 no
H101 . N10 . H102 . 114.6 no
C2 . C11 . C12 . 112.24(18) yes
C2 . C11 . H111 . 109.2 no
C12 . C11 . H111 . 108.8 no
C2 . C11 . H112 . 109.3 no
C12 . C11 . H112 . 109.1 no
H111 . C11 . H112 . 108.0 no
C11 . C12 . H121 . 110.7 no
C11 . C12 . H122 . 108.3 no
H121 . C12 . H122 . 109.8 no
C11 . C12 . H123 . 109.4 no
H121 . C12 . H123 . 109.4 no
H122 . C12 . H123 . 109.3 no
C22 . N21 . C26 . 117.95(13) yes
N21 . C22 . C23 . 121.55(15) yes
N21 . C22 . C31 . 117.71(14) yes
C23 . C22 . C31 . 120.74(15) yes
C22 . C23 . C24 . 119.77(15) yes
C22 . C23 . H231 . 119.4 no
C24 . C23 . H231 . 120.8 no
C23 . C24 . C25 . 118.55(14) yes
C23 . C24 . C27 . 121.55(14) yes
C25 . C24 . C27 . 119.89(14) yes
C24 . C25 . C26 . 117.67(15) yes
C24 . C25 . H251 . 121.9 no
C26 . C25 . H251 . 120.4 no
C25 . C26 . N21 . 124.47(15) yes
C25 . C26 . H261 . 118.6 no
N21 . C26 . H261 . 116.9 no
C24 . C27 . S28 . 115.53(11) yes
C24 . C27 . N30 . 121.49(13) yes
S28 . C27 . N30 . 122.97(11) yes
C27 . S28 . O29 . 106.34(7) yes
C27 . N30 . H301 . 121.0 no
C27 . N30 . H302 . 120.6 no
H301 . N30 . H302 . 118.3 no
C22 . C31 . C32 . 113.78(15) yes
C22 . C31 . H311 . 109.6 no
C32 . C31 . H311 . 107.9 no
C22 . C31 . H312 . 106.8 no
C32 . C31 . H312 . 109.3 no
H311 . C31 . H312 . 109.3 no
C31 . C32 . H321 . 109.4 no
C31 . C32 . H322 . 108.8 no
H321 . C32 . H322 . 111.0 no
C31 . C32 . H323 . 109.9 no
H321 . C32 . H323 . 109.5 no
H322 . C32 . H323 . 108.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N10 . H101 . O29 1_765 167.74(5) 0.873 1.897 2.756(3) yes
N10 . H102 . O29 2_657 148.01(5) 0.895 2.155 2.953(3) yes
C26 . H261 . O29 1_655 122.82(5) 0.945 2.550 3.164(3) yes
N30 . H301 . O9 1_455 177.39(6) 0.879 1.920 2.799(3) yes
N30 . H302 . N21 1_455 164.05(5) 0.873 2.300 3.148(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 29/01/15 at 11:35:21
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE N   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE N   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 29/01/15 at 11:35:21
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
