# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_35
_database_code_depnum_ccdc_archive 'CCDC 1815202'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2017-08-28
_audit_creation_method           CRYSTALS_ver_14.61_build_6236

_oxford_structure_analysis_title 051eaa17
_chemical_name_systematic        .
_chemical_melting_point          395-400

_cell_length_a                   10.0967(3)
_cell_length_b                   11.1751(3)
_cell_length_c                   13.8100(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.850(3)
_cell_angle_gamma                90
_cell_volume                     1506.16(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

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

# Given Formula = C14 H18 N2 O5 S1 
# Dc =      1.44 Fooo =    688.00 Mu =     21.53 M =    326.37
# Found Formula = C14 H18 N2 O5 S1 
# Dc =      1.44 FOOO =    688.00 Mu =     21.53 M =    326.37

_chemical_formula_sum            'C14 H18 N2 O5 S1'
_chemical_formula_moiety         'C14 H18 N2 O5 S1'
_chemical_compound_source        synthetic
_chemical_formula_weight         326.37


_cell_measurement_reflns_used    7675
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_max          0.30

_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.153

# Sheldrick geometric approximatio 0.76 0.79 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.79
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_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      150
_diffrn_reflns_number            14431
_reflns_number_total             3125
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0288
# Number of reflections with Friedels Law is 3125 
# Theoretical number of reflections is about 6313 


_diffrn_reflns_theta_min         4.531
_diffrn_reflns_theta_max         76.278
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        74.753
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.93
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.28


# 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         3124
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0319
_refine_ls_wR_factor_ref         0.0803
_refine_ls_goodness_of_fit_ref   1.0085
_refine_ls_shift/su_max          0.0006150
_refine_ls_shift/su_mean         0.0000483


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3124
_refine_ls_R_factor_all          0.0319
_refine_ls_wR_factor_all         0.0803

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2897
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_gt          0.0781

# 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 Fsqd
_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= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.68P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# 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 0.40456(10) 1.06744(9) 0.34891(8) 0.0203 1.0000 Uani . . . . . .
C2 C 0.43250(13) 1.19681(11) 0.34442(10) 0.0244 1.0000 Uani . . . . . .
C3 C 0.48819(13) 1.23966(12) 0.45090(10) 0.0266 1.0000 Uani . . . . . .
C4 C 0.38399(13) 1.21401(12) 0.51057(10) 0.0253 1.0000 Uani . . . . . .
C5 C 0.33583(12) 1.08714(11) 0.49342(9) 0.0200 1.0000 Uani . . . . . .
N6 N 0.34305(10) 1.02046(9) 0.41939(8) 0.0190 1.0000 Uani . . . . . .
S7 S 0.36149(3) 0.98817(3) 0.24255(2) 0.0232 1.0000 Uani . . . . . .
O8 O 0.42831(10) 1.04833(11) 0.17651(7) 0.0347 1.0000 Uani . . . . . .
O9 O 0.39154(10) 0.86545(9) 0.26885(7) 0.0304 1.0000 Uani . . . . . .
C10 C 0.18276(13) 1.00201(12) 0.19628(9) 0.0240 1.0000 Uani . . . . . .
C11 C 0.12872(16) 1.09557(16) 0.13217(12) 0.0385 1.0000 Uani . . . . . .
C12 C -0.01240(16) 1.10761(16) 0.09924(12) 0.0429 1.0000 Uani . . . . . .
C13 C -0.10013(14) 1.02775(14) 0.12864(11) 0.0304 1.0000 Uani . . . . . .
C14 C -0.04378(14) 0.93452(13) 0.19238(10) 0.0280 1.0000 Uani . . . . . .
C15 C 0.09727(14) 0.92125(12) 0.22691(10) 0.0251 1.0000 Uani . . . . . .
C16 C -0.25346(15) 1.04351(16) 0.09225(13) 0.0403 1.0000 Uani . . . . . .
O17 O 0.30993(11) 1.25805(9) 0.30018(8) 0.0339 1.0000 Uani . . . . . .
C18 C 0.27054(12) 1.03234(12) 0.56870(9) 0.0226 1.0000 Uani . . . . . .
O19 O 0.25259(11) 1.08892(10) 0.63886(8) 0.0361 1.0000 Uani . . . . . .
O20 O 0.23428(9) 0.91865(8) 0.55061(7) 0.0256 1.0000 Uani . . . . . .
C21 C 0.17446(14) 0.85917(14) 0.62374(11) 0.0307 1.0000 Uani . . . . . .
C22 C 0.02146(14) 0.87626(13) 0.59740(11) 0.0313 1.0000 Uani . . . . . .
H21 H 0.5008 1.2076 0.3060 0.0277 1.0000 Uiso R . . . . .
H31 H 0.5033 1.3241 0.4459 0.0309 1.0000 Uiso R . . . . .
H32 H 0.5766 1.1980 0.4829 0.0302 1.0000 Uiso R . . . . .
H41 H 0.4213 1.2285 0.5814 0.0292 1.0000 Uiso R . . . . .
H42 H 0.3045 1.2660 0.4870 0.0290 1.0000 Uiso R . . . . .
H111 H 0.1896 1.1513 0.1123 0.0446 1.0000 Uiso R . . . . .
H121 H -0.0494 1.1737 0.0557 0.0498 1.0000 Uiso R . . . . .
H141 H -0.1015 0.8776 0.2138 0.0331 1.0000 Uiso R . . . . .
H151 H 0.1373 0.8569 0.2709 0.0302 1.0000 Uiso R . . . . .
H161 H -0.2997 0.9902 0.1296 0.0602 1.0000 Uiso R . . . . .
H162 H -0.2772 1.1268 0.1032 0.0595 1.0000 Uiso R . . . . .
H163 H -0.2847 1.0278 0.0218 0.0598 1.0000 Uiso R . . . . .
H211 H 0.2161 0.8913 0.6904 0.0355 1.0000 Uiso R . . . . .
H212 H 0.1984 0.7734 0.6218 0.0364 1.0000 Uiso R . . . . .
H222 H -0.0148 0.8309 0.6457 0.0457 1.0000 Uiso R . . . . .
H223 H 0.0007 0.9582 0.6001 0.0448 1.0000 Uiso R . . . . .
H221 H -0.0192 0.8435 0.5302 0.0450 1.0000 Uiso R . . . . .
H171 H 0.3169 1.2935 0.2491 0.0507 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.62(14)
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 . 1.4773(16) yes
N1 . N6 . 1.3851(14) yes
N1 . S7 . 1.6745(11) yes
C2 . C3 . 1.5112(19) yes
C2 . O17 . 1.4091(16) yes
C2 . H21 . 0.980 no
C3 . C4 . 1.5207(18) yes
C3 . H31 . 0.961 no
C3 . H32 . 1.004 no
C4 . C5 . 1.4978(17) yes
C4 . H41 . 0.968 no
C4 . H42 . 0.977 no
C5 . N6 . 1.2823(16) yes
C5 . C18 . 1.4971(17) yes
S7 . O8 . 1.4332(10) yes
S7 . O9 . 1.4312(11) yes
S7 . C10 . 1.7600(13) yes
C10 . C11 . 1.388(2) yes
C10 . C15 . 1.3876(18) yes
C11 . C12 . 1.387(2) yes
C11 . H111 . 0.962 no
C12 . C13 . 1.389(2) yes
C12 . H121 . 0.965 no
C13 . C14 . 1.388(2) yes
C13 . C16 . 1.510(2) yes
C14 . C15 . 1.3891(19) yes
C14 . H141 . 0.959 no
C15 . H151 . 0.961 no
C16 . H161 . 0.981 no
C16 . H162 . 0.982 no
C16 . H163 . 0.959 no
O17 . H171 . 0.828 no
C18 . O19 . 1.2089(16) yes
C18 . O20 . 1.3280(16) yes
O20 . C21 . 1.4627(15) yes
C21 . C22 . 1.5056(19) yes
C21 . H211 . 0.977 no
C21 . H212 . 0.990 no
C22 . H222 . 0.981 no
C22 . H223 . 0.943 no
C22 . H221 . 0.984 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 . N6 . 121.68(10) yes
C2 . N1 . S7 . 119.36(8) yes
N6 . N1 . S7 . 110.70(8) yes
N1 . C2 . C3 . 107.26(10) yes
N1 . C2 . O17 . 109.73(10) yes
C3 . C2 . O17 . 109.54(11) yes
N1 . C2 . H21 . 108.1 no
C3 . C2 . H21 . 110.5 no
O17 . C2 . H21 . 111.5 no
C2 . C3 . C4 . 109.33(10) yes
C2 . C3 . H31 . 105.5 no
C4 . C3 . H31 . 111.6 no
C2 . C3 . H32 . 110.4 no
C4 . C3 . H32 . 109.6 no
H31 . C3 . H32 . 110.3 no
C3 . C4 . C5 . 109.54(10) yes
C3 . C4 . H41 . 111.9 no
C5 . C4 . H41 . 110.2 no
C3 . C4 . H42 . 109.3 no
C5 . C4 . H42 . 107.8 no
H41 . C4 . H42 . 108.1 no
C4 . C5 . N6 . 126.41(11) yes
C4 . C5 . C18 . 117.41(11) yes
N6 . C5 . C18 . 116.17(11) yes
N1 . N6 . C5 . 117.86(10) yes
N1 . S7 . O8 . 104.55(6) yes
N1 . S7 . O9 . 107.08(6) yes
O8 . S7 . O9 . 120.48(6) yes
N1 . S7 . C10 . 106.47(6) yes
O8 . S7 . C10 . 109.50(6) yes
O9 . S7 . C10 . 107.90(6) yes
S7 . C10 . C11 . 119.77(10) yes
S7 . C10 . C15 . 119.49(10) yes
C11 . C10 . C15 . 120.71(12) yes
C10 . C11 . C12 . 119.02(13) yes
C10 . C11 . H111 . 119.6 no
C12 . C11 . H111 . 121.4 no
C11 . C12 . C13 . 121.35(14) yes
C11 . C12 . H121 . 118.7 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 118.62(13) yes
C12 . C13 . C16 . 120.25(14) yes
C14 . C13 . C16 . 121.13(13) yes
C13 . C14 . C15 . 121.01(13) yes
C13 . C14 . H141 . 120.7 no
C15 . C14 . H141 . 118.3 no
C14 . C15 . C10 . 119.28(12) yes
C14 . C15 . H151 . 121.7 no
C10 . C15 . H151 . 119.1 no
C13 . C16 . H161 . 109.9 no
C13 . C16 . H162 . 109.2 no
H161 . C16 . H162 . 109.1 no
C13 . C16 . H163 . 111.0 no
H161 . C16 . H163 . 110.2 no
H162 . C16 . H163 . 107.4 no
C2 . O17 . H171 . 110.2 no
C5 . C18 . O19 . 121.71(12) yes
C5 . C18 . O20 . 114.20(10) yes
O19 . C18 . O20 . 124.08(12) yes
C18 . O20 . C21 . 116.59(10) yes
O20 . C21 . C22 . 110.81(11) yes
O20 . C21 . H211 . 109.2 no
C22 . C21 . H211 . 110.4 no
O20 . C21 . H212 . 105.9 no
C22 . C21 . H212 . 111.0 no
H211 . C21 . H212 . 109.3 no
C21 . C22 . H222 . 108.0 no
C21 . C22 . H223 . 109.8 no
H222 . C22 . H223 . 110.4 no
C21 . C22 . H221 . 109.6 no
H222 . C22 . H221 . 108.1 no
H223 . C22 . H221 . 110.9 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
C2 . H21 . O9 4_655 140 0.98 2.44 3.253(2) yes
C3 . H32 . O20 2_676 144 1.00 2.45 3.318(2) yes
C14 . H141 . O17 4_545 156 0.96 2.46 3.356(2) yes
O17 . H171 . O19 3_574 152 0.83 1.99 2.750(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 0 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
