# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_24
_database_code_depnum_ccdc_archive 'CCDC 1453550'
_audit_update_record             
;
2016-02-16 deposited with the CCDC.
2016-05-09 downloaded from the CCDC.
;
#==============================================================================

_audit_creation_date             2015-09-17
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 'X:\SIMS\User\MT9981-24-05-14\010 At 17:46 on'
_chemical_name_systematic        24
_chemical_melting_point          'not measured'

_cell_length_a                   9.66860(10)
_cell_length_b                   35.1961(4)
_cell_length_c                   15.4447(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.1030(12)
_cell_angle_gamma                90
_cell_volume                     5174.29(11)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,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 0.0033 0.0016 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'
I -0.488 1.723 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 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 0.0106 0.0060 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 0.119 0.1234 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            8

# Given Formula = C23 H27 I1 N4 O5 S2 
# Dc =      1.62 Fooo =   2544.00 Mu =     14.40 M =   1261.06
# Found Formula = C23 H27 I1 N4 O5 S2 
# Dc =      1.62 FOOO =   2544.00 Mu =     14.40 M =   1261.05

_chemical_formula_sum            'C23 H27 I1 N4 O5 S2'
_chemical_formula_moiety         'C23 H27 I1 N4 O5 S2'
_chemical_compound_source        synthesis
_chemical_formula_weight         630.53


_cell_measurement_reflns_used    12155
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    100

_exptl_crystal_description       needles
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.005
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_max          0.020

_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2544
_exptl_absorpt_coefficient_mu    1.440

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       'profile data from ω-scans'

# 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       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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      100
_diffrn_reflns_number            87503
_reflns_number_total             14386
_diffrn_reflns_av_R_equivalents  0.083
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 14386 
# Theoretical number of reflections is about 24488 


_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         29.305
_diffrn_measured_fraction_theta_max 0.926

_diffrn_reflns_theta_full        25.203
_diffrn_measured_fraction_theta_full 0.993


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              49
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   1.40
_oxford_diffrn_Wilson_scale      0.66

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

_refine_diff_density_min         -0.78
_refine_diff_density_max         0.96


# 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         12148
_refine_ls_number_restraints     0
_refine_ls_number_parameters     631
_oxford_refine_ls_R_factor_ref   0.0525
_refine_ls_wR_factor_ref         0.0763
_refine_ls_goodness_of_fit_ref   0.9203
_refine_ls_shift/su_max          0.0018958
_refine_ls_shift/su_mean         0.0000437


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        12148
_refine_ls_R_factor_all          0.0525
_refine_ls_wR_factor_all         0.0763

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9627
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_gt          0.0660

# 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    mixed #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: 
 961. 0.141E+04 822. 295. 56.0 
;

# 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
I1 I 0.51300(2) 0.394904(6) 0.677628(15) 0.0173 1.0000 Uani . . . . . .
C2 C 0.3431(4) 0.41090(10) 0.5822(2) 0.0154 1.0000 Uani . . . . . .
C3 C 0.2886(4) 0.38431(9) 0.5179(2) 0.0138 1.0000 Uani . . . . . .
N4 N 0.3421(3) 0.34792(8) 0.51169(19) 0.0154 1.0000 Uani . . . . . .
C5 C 0.2653(4) 0.33009(10) 0.4470(2) 0.0178 1.0000 Uani . . . . . .
S6 S 0.12041(10) 0.35443(3) 0.38819(6) 0.0193 1.0000 Uani . . . . . .
C7 C 0.1691(4) 0.39362(10) 0.4563(2) 0.0171 1.0000 Uani . . . . . .
C8 C 0.1069(4) 0.42907(10) 0.4558(2) 0.0178 1.0000 Uani . . . . . .
C9 C 0.1644(4) 0.45572(10) 0.5176(2) 0.0174 1.0000 Uani . . . . . .
C10 C 0.2827(4) 0.44669(10) 0.5821(2) 0.0139 1.0000 Uani . . . . . .
N11 N 0.3438(3) 0.47389(8) 0.6446(2) 0.0163 1.0000 Uani . . . . . .
C12 C 0.2711(4) 0.50013(10) 0.6842(2) 0.0152 1.0000 Uani . . . . . .
O13 O 0.1429(3) 0.50487(8) 0.66761(17) 0.0198 1.0000 Uani . . . . . .
N14 N 0.3573(3) 0.52118(9) 0.7462(2) 0.0161 1.0000 Uani . . . . . .
C15 C 0.3152(4) 0.55250(10) 0.7892(2) 0.0147 1.0000 Uani . . . . . .
S16 S 0.17038(9) 0.57952(2) 0.74730(6) 0.0161 1.0000 Uani . . . . . .
C17 C 0.2060(4) 0.61197(10) 0.8332(2) 0.0170 1.0000 Uani . . . . . .
C18 C 0.3213(4) 0.60150(10) 0.8912(2) 0.0184 1.0000 Uani . . . . . .
C19 C 0.3864(3) 0.56737(10) 0.8670(2) 0.0150 1.0000 Uani . . . . . .
C20 C 0.5092(4) 0.54853(10) 0.9181(2) 0.0160 1.0000 Uani . . . . . .
O21 O 0.5534(3) 0.56521(7) 0.99630(16) 0.0188 1.0000 Uani . . . . . .
C22 C 0.6733(4) 0.54691(11) 1.0509(2) 0.0187 1.0000 Uani . . . . . .
C23 C 0.7175(5) 0.57124(14) 1.1305(3) 0.0339 1.0000 Uani . . . . . .
O24 O 0.5640(3) 0.52009(7) 0.89386(17) 0.0201 1.0000 Uani . . . . . .
C25 C 0.1091(4) 0.64548(10) 0.8345(2) 0.0191 1.0000 Uani . . . . . .
C26 C 0.1183(4) 0.66217(11) 0.9258(3) 0.0239 1.0000 Uani . . . . . .
N27 N 0.3030(3) 0.29345(9) 0.4253(2) 0.0181 1.0000 Uani . . . . . .
C28 C 0.4375(4) 0.27818(11) 0.4717(3) 0.0228 1.0000 Uani . . . . . .
C29 C 0.2109(4) 0.27164(11) 0.3668(3) 0.0216 1.0000 Uani . . . . . .
O30 O 0.2671(3) 0.23700(7) 0.36016(18) 0.0238 1.0000 Uani . . . . . .
C31 C 0.1775(4) 0.20597(10) 0.3147(3) 0.0212 1.0000 Uani . . . . . .
C32 C 0.0571(4) 0.19867(12) 0.3637(3) 0.0285 1.0000 Uani . . . . . .
C33 C 0.2782(4) 0.17253(10) 0.3249(3) 0.0236 1.0000 Uani . . . . . .
C34 C 0.1293(4) 0.21577(11) 0.2174(3) 0.0236 1.0000 Uani . . . . . .
O35 O 0.0995(3) 0.28303(8) 0.3282(2) 0.0289 1.0000 Uani . . . . . .
I101 I 0.98667(2) 0.391310(6) 0.664745(15) 0.0173 1.0000 Uani . . . . . .
C102 C 0.8232(3) 0.41228(10) 0.5703(2) 0.0147 1.0000 Uani . . . . . .
C103 C 0.7611(4) 0.38828(10) 0.5027(2) 0.0158 1.0000 Uani . . . . . .
N104 N 0.8028(3) 0.35156(8) 0.4882(2) 0.0173 1.0000 Uani . . . . . .
C105 C 0.7252(4) 0.33797(10) 0.4184(2) 0.0156 1.0000 Uani . . . . . .
S106 S 0.59150(9) 0.36713(2) 0.36282(6) 0.0168 1.0000 Uani . . . . . .
C107 C 0.6450(4) 0.40161(10) 0.4423(2) 0.0150 1.0000 Uani . . . . . .
C108 C 0.5916(4) 0.43817(10) 0.4481(2) 0.0173 1.0000 Uani . . . . . .
C109 C 0.6573(4) 0.46160(10) 0.5147(2) 0.0150 1.0000 Uani . . . . . .
C110 C 0.7731(4) 0.44915(10) 0.5763(2) 0.0136 1.0000 Uani . . . . . .
N111 N 0.8406(3) 0.47412(8) 0.64205(19) 0.0152 1.0000 Uani . . . . . .
C112 C 0.7734(4) 0.49997(10) 0.6860(2) 0.0150 1.0000 Uani . . . . . .
O113 O 0.6455(2) 0.50494(7) 0.67415(17) 0.0167 1.0000 Uani . . . . . .
N114 N 0.8652(3) 0.52009(9) 0.7469(2) 0.0169 1.0000 Uani . . . . . .
C115 C 0.8278(4) 0.55038(10) 0.7955(2) 0.0160 1.0000 Uani . . . . . .
S116 S 0.69029(9) 0.58065(2) 0.75556(6) 0.0165 1.0000 Uani . . . . . .
C117 C 0.7296(4) 0.61013(10) 0.8471(2) 0.0162 1.0000 Uani . . . . . .
C118 C 0.8411(4) 0.59665(10) 0.9038(2) 0.0154 1.0000 Uani . . . . . .
C119 C 0.9001(4) 0.56265(10) 0.8752(2) 0.0153 1.0000 Uani . . . . . .
C120 C 1.0237(4) 0.54235(10) 0.9215(2) 0.0157 1.0000 Uani . . . . . .
O121 O 1.0725(3) 0.55794(7) 1.00008(16) 0.0175 1.0000 Uani . . . . . .
C122 C 1.1964(4) 0.53949(10) 1.0500(2) 0.0183 1.0000 Uani . . . . . .
C123 C 1.2453(5) 0.56260(13) 1.1304(3) 0.0361 1.0000 Uani . . . . . .
O124 O 1.0761(3) 0.51461(7) 0.89307(17) 0.0195 1.0000 Uani . . . . . .
C125 C 0.6439(4) 0.64530(10) 0.8520(3) 0.0209 1.0000 Uani . . . . . .
C126 C 0.6705(5) 0.66400(12) 0.9429(3) 0.0340 1.0000 Uani . . . . . .
N127 N 0.7470(3) 0.30101(8) 0.3909(2) 0.0171 1.0000 Uani . . . . . .
C129 C 0.6824(4) 0.28865(10) 0.3085(2) 0.0192 1.0000 Uani . . . . . .
O130 O 0.7243(3) 0.25365(7) 0.29143(17) 0.0197 1.0000 Uani . . . . . .
C131 C 0.6590(4) 0.23516(11) 0.2074(2) 0.0208 1.0000 Uani . . . . . .
C134 C 0.5006(4) 0.23262(13) 0.2021(3) 0.0281 1.0000 Uani . . . . . .
C133 C 0.7243(5) 0.19602(11) 0.2160(3) 0.0299 1.0000 Uani . . . . . .
C132 C 0.6987(5) 0.25667(12) 0.1305(3) 0.0299 1.0000 Uani . . . . . .
O135 O 0.5976(3) 0.30782(8) 0.26037(18) 0.0267 1.0000 Uani . . . . . .
C128 C 0.8433(4) 0.27733(11) 0.4522(3) 0.0237 1.0000 Uani . . . . . .
H81 H 0.0271 0.4349 0.4145 0.0207 1.0000 Uiso R . . . . .
H91 H 0.1259 0.4799 0.5165 0.0217 1.0000 Uiso R . . . . .
H181 H 0.3551 0.6152 0.9420 0.0226 1.0000 Uiso R . . . . .
H221 H 0.7489 0.5437 1.0179 0.0223 1.0000 Uiso R . . . . .
H222 H 0.6431 0.5221 1.0695 0.0233 1.0000 Uiso R . . . . .
H232 H 0.7946 0.5594 1.1687 0.0529 1.0000 Uiso R . . . . .
H231 H 0.7463 0.5958 1.1141 0.0527 1.0000 Uiso R . . . . .
H233 H 0.6398 0.5742 1.1615 0.0529 1.0000 Uiso R . . . . .
H252 H 0.1353 0.6649 0.7966 0.0250 1.0000 Uiso R . . . . .
H251 H 0.0132 0.6375 0.8123 0.0250 1.0000 Uiso R . . . . .
H261 H 0.0525 0.6826 0.9254 0.0362 1.0000 Uiso R . . . . .
H263 H 0.2114 0.6718 0.9481 0.0355 1.0000 Uiso R . . . . .
H262 H 0.0978 0.6431 0.9659 0.0356 1.0000 Uiso R . . . . .
H281 H 0.4834 0.2642 0.4315 0.0338 1.0000 Uiso R . . . . .
H282 H 0.4207 0.2621 0.5192 0.0342 1.0000 Uiso R . . . . .
H283 H 0.4963 0.2990 0.4957 0.0344 1.0000 Uiso R . . . . .
H321 H 0.0102 0.1757 0.3414 0.0423 1.0000 Uiso R . . . . .
H322 H -0.0086 0.2193 0.3562 0.0425 1.0000 Uiso R . . . . .
H323 H 0.0950 0.1957 0.4250 0.0427 1.0000 Uiso R . . . . .
H331 H 0.2284 0.1501 0.3016 0.0367 1.0000 Uiso R . . . . .
H332 H 0.3162 0.1681 0.3862 0.0370 1.0000 Uiso R . . . . .
H333 H 0.3554 0.1770 0.2941 0.0368 1.0000 Uiso R . . . . .
H341 H 0.0857 0.1938 0.1867 0.0369 1.0000 Uiso R . . . . .
H342 H 0.0625 0.2363 0.2120 0.0367 1.0000 Uiso R . . . . .
H343 H 0.2087 0.2229 0.1915 0.0369 1.0000 Uiso R . . . . .
H1081 H 0.5143 0.4466 0.4089 0.0209 1.0000 Uiso R . . . . .
H1091 H 0.6244 0.4863 0.5192 0.0181 1.0000 Uiso R . . . . .
H1181 H 0.8766 0.6081 0.9573 0.0189 1.0000 Uiso R . . . . .
H1222 H 1.2700 0.5379 1.0146 0.0223 1.0000 Uiso R . . . . .
H1221 H 1.1730 0.5140 1.0670 0.0217 1.0000 Uiso R . . . . .
H1231 H 1.3242 0.5505 1.1657 0.0539 1.0000 Uiso R . . . . .
H1233 H 1.2725 0.5876 1.1136 0.0538 1.0000 Uiso R . . . . .
H1232 H 1.1705 0.5647 1.1637 0.0535 1.0000 Uiso R . . . . .
H1251 H 0.6644 0.6633 0.8092 0.0255 1.0000 Uiso R . . . . .
H1252 H 0.5459 0.6387 0.8375 0.0259 1.0000 Uiso R . . . . .
H1261 H 0.6135 0.6864 0.9426 0.0520 1.0000 Uiso R . . . . .
H1262 H 0.7688 0.6710 0.9592 0.0520 1.0000 Uiso R . . . . .
H1263 H 0.6475 0.6464 0.9862 0.0521 1.0000 Uiso R . . . . .
H1342 H 0.4639 0.2140 0.1592 0.0426 1.0000 Uiso R . . . . .
H1341 H 0.4561 0.2568 0.1861 0.0429 1.0000 Uiso R . . . . .
H1343 H 0.4792 0.2246 0.2572 0.0425 1.0000 Uiso R . . . . .
H1332 H 0.6862 0.1810 0.1660 0.0439 1.0000 Uiso R . . . . .
H1331 H 0.8245 0.1979 0.2194 0.0441 1.0000 Uiso R . . . . .
H1333 H 0.7048 0.1839 0.2686 0.0437 1.0000 Uiso R . . . . .
H1322 H 0.6682 0.2423 0.0781 0.0461 1.0000 Uiso R . . . . .
H1321 H 0.6528 0.2811 0.1256 0.0459 1.0000 Uiso R . . . . .
H1323 H 0.7992 0.2599 0.1390 0.0463 1.0000 Uiso R . . . . .
H1282 H 0.8247 0.2511 0.4384 0.0350 1.0000 Uiso R . . . . .
H1281 H 0.9376 0.2836 0.4464 0.0356 1.0000 Uiso R . . . . .
H1283 H 0.8283 0.2824 0.5109 0.0349 1.0000 Uiso R . . . . .
H1111 H 0.9303 0.4755 0.6500 0.0177 1.0000 Uiso . . . . . .
H111 H 0.4339 0.4746 0.6574 0.0209 1.0000 Uiso . . . . . .
H141 H 0.4448 0.5144 0.7595 0.0200 1.0000 Uiso . . . . . .
H1141 H 0.9498 0.5117 0.7607 0.0214 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.2335(19)
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
I1 . C2 . 2.082(3) yes
C2 . C3 . 1.399(5) yes
C2 . C10 . 1.388(5) yes
C3 . N4 . 1.391(4) yes
C3 . C7 . 1.401(5) yes
N4 . C5 . 1.297(4) yes
C5 . S6 . 1.753(4) yes
C5 . N27 . 1.397(5) yes
S6 . C7 . 1.748(3) yes
C7 . C8 . 1.384(5) yes
C8 . C9 . 1.383(5) yes
C8 . H81 . 0.934 no
C9 . C10 . 1.415(5) yes
C9 . H91 . 0.929 no
C10 . N11 . 1.414(4) yes
N11 . C12 . 1.368(5) yes
N11 . H111 . 0.859 no
C12 . O13 . 1.233(4) yes
C12 . N14 . 1.371(4) yes
N14 . C15 . 1.385(4) yes
N14 . H141 . 0.867 no
C15 . S16 . 1.722(3) yes
C15 . C19 . 1.379(5) yes
S16 . C17 . 1.738(4) yes
C17 . C18 . 1.353(5) yes
C17 . C25 . 1.508(5) yes
C18 . C19 . 1.436(5) yes
C18 . H181 . 0.930 no
C19 . C20 . 1.464(5) yes
C20 . O21 . 1.344(4) yes
C20 . O24 . 1.222(4) yes
O21 . C22 . 1.459(4) yes
C22 . C23 . 1.498(5) yes
C22 . H221 . 0.968 no
C22 . H222 . 0.980 no
C23 . H232 . 0.961 no
C23 . H231 . 0.957 no
C23 . H233 . 0.964 no
C25 . C26 . 1.517(5) yes
C25 . H252 . 0.962 no
C25 . H251 . 0.972 no
C26 . H261 . 0.959 no
C26 . H263 . 0.967 no
C26 . H262 . 0.958 no
N27 . C28 . 1.472(5) yes
N27 . C29 . 1.384(5) yes
C28 . H281 . 0.960 no
C28 . H282 . 0.964 no
C28 . H283 . 0.961 no
C29 . O30 . 1.346(5) yes
C29 . O35 . 1.205(5) yes
O30 . C31 . 1.491(4) yes
C31 . C32 . 1.518(6) yes
C31 . C33 . 1.518(5) yes
C31 . C34 . 1.532(5) yes
C32 . H321 . 0.961 no
C32 . H322 . 0.959 no
C32 . H323 . 0.959 no
C33 . H331 . 0.960 no
C33 . H332 . 0.966 no
C33 . H333 . 0.965 no
C34 . H341 . 0.964 no
C34 . H342 . 0.962 no
C34 . H343 . 0.960 no
I101 . C102 . 2.089(3) yes
C102 . C103 . 1.394(5) yes
C102 . C110 . 1.394(5) yes
C103 . N104 . 1.383(4) yes
C103 . C107 . 1.408(5) yes
N104 . C105 . 1.292(5) yes
C105 . S106 . 1.753(3) yes
C105 . N127 . 1.396(4) yes
S106 . C107 . 1.739(3) yes
C107 . C108 . 1.395(5) yes
C108 . C109 . 1.384(5) yes
C108 . H1081 . 0.924 no
C109 . C110 . 1.406(5) yes
C109 . H1091 . 0.933 no
C110 . N111 . 1.413(4) yes
N111 . C112 . 1.366(5) yes
N111 . H1111 . 0.855 no
C112 . O113 . 1.230(4) yes
C112 . N114 . 1.372(4) yes
N114 . C115 . 1.388(5) yes
N114 . H1141 . 0.860 no
C115 . S116 . 1.731(4) yes
C115 . C119 . 1.375(5) yes
S116 . C117 . 1.741(4) yes
C117 . C118 . 1.350(5) yes
C117 . C125 . 1.498(5) yes
C118 . C119 . 1.429(5) yes
C118 . H1181 . 0.928 no
C119 . C120 . 1.466(5) yes
C120 . O121 . 1.340(4) yes
C120 . O124 . 1.217(4) yes
O121 . C122 . 1.459(4) yes
C122 . C123 . 1.490(5) yes
C122 . H1222 . 0.972 no
C122 . H1221 . 0.973 no
C123 . H1231 . 0.957 no
C123 . H1233 . 0.965 no
C123 . H1232 . 0.961 no
C125 . C126 . 1.531(5) yes
C125 . H1251 . 0.960 no
C125 . H1252 . 0.963 no
C126 . H1261 . 0.963 no
C126 . H1262 . 0.971 no
C126 . H1263 . 0.967 no
N127 . C129 . 1.386(5) yes
N127 . C128 . 1.465(4) yes
C129 . O130 . 1.338(4) yes
C129 . O135 . 1.211(5) yes
O130 . C131 . 1.490(4) yes
C131 . C134 . 1.522(5) yes
C131 . C133 . 1.512(5) yes
C131 . C132 . 1.513(6) yes
C134 . H1342 . 0.955 no
C134 . H1341 . 0.967 no
C134 . H1343 . 0.954 no
C133 . H1332 . 0.955 no
C133 . H1331 . 0.963 no
C133 . H1333 . 0.965 no
C132 . H1322 . 0.957 no
C132 . H1321 . 0.964 no
C132 . H1323 . 0.964 no
C128 . H1282 . 0.957 no
C128 . H1281 . 0.957 no
C128 . H1283 . 0.960 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
I1 . C2 . C3 . 118.3(2) yes
I1 . C2 . C10 . 121.7(2) yes
C3 . C2 . C10 . 120.0(3) yes
C2 . C3 . N4 . 124.5(3) yes
C2 . C3 . C7 . 119.3(3) yes
N4 . C3 . C7 . 116.1(3) yes
C3 . N4 . C5 . 109.2(3) yes
N4 . C5 . S6 . 117.4(3) yes
N4 . C5 . N27 . 119.6(3) yes
S6 . C5 . N27 . 123.0(3) yes
C5 . S6 . C7 . 88.15(17) yes
S6 . C7 . C3 . 109.1(3) yes
S6 . C7 . C8 . 129.6(3) yes
C3 . C7 . C8 . 121.3(3) yes
C7 . C8 . C9 . 119.1(3) yes
C7 . C8 . H81 . 120.5 no
C9 . C8 . H81 . 120.4 no
C8 . C9 . C10 . 120.7(3) yes
C8 . C9 . H91 . 119.9 no
C10 . C9 . H91 . 119.3 no
C9 . C10 . C2 . 119.5(3) yes
C9 . C10 . N11 . 121.2(3) yes
C2 . C10 . N11 . 119.2(3) yes
C10 . N11 . C12 . 125.2(3) yes
C10 . N11 . H111 . 117.5 no
C12 . N11 . H111 . 117.3 no
N11 . C12 . O13 . 125.2(3) yes
N11 . C12 . N14 . 112.3(3) yes
O13 . C12 . N14 . 122.5(3) yes
C12 . N14 . C15 . 124.8(3) yes
C12 . N14 . H141 . 117.7 no
C15 . N14 . H141 . 117.4 no
N14 . C15 . S16 . 123.2(2) yes
N14 . C15 . C19 . 125.2(3) yes
S16 . C15 . C19 . 111.5(3) yes
C15 . S16 . C17 . 92.14(17) yes
S16 . C17 . C18 . 110.9(3) yes
S16 . C17 . C25 . 118.9(3) yes
C18 . C17 . C25 . 130.2(3) yes
C17 . C18 . C19 . 113.8(3) yes
C17 . C18 . H181 . 123.0 no
C19 . C18 . H181 . 123.2 no
C18 . C19 . C15 . 111.7(3) yes
C18 . C19 . C20 . 126.1(3) yes
C15 . C19 . C20 . 122.1(3) yes
C19 . C20 . O21 . 112.8(3) yes
C19 . C20 . O24 . 124.1(3) yes
O21 . C20 . O24 . 123.2(3) yes
C20 . O21 . C22 . 114.9(3) yes
O21 . C22 . C23 . 107.8(3) yes
O21 . C22 . H221 . 110.1 no
C23 . C22 . H221 . 111.5 no
O21 . C22 . H222 . 108.4 no
C23 . C22 . H222 . 109.0 no
H221 . C22 . H222 . 110.0 no
C22 . C23 . H232 . 109.5 no
C22 . C23 . H231 . 110.7 no
H232 . C23 . H231 . 108.9 no
C22 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 109.3 no
H231 . C23 . H233 . 108.8 no
C17 . C25 . C26 . 112.3(3) yes
C17 . C25 . H252 . 108.6 no
C26 . C25 . H252 . 108.1 no
C17 . C25 . H251 . 109.0 no
C26 . C25 . H251 . 109.6 no
H252 . C25 . H251 . 109.1 no
C25 . C26 . H261 . 110.7 no
C25 . C26 . H263 . 111.4 no
H261 . C26 . H263 . 108.5 no
C25 . C26 . H262 . 110.2 no
H261 . C26 . H262 . 108.5 no
H263 . C26 . H262 . 107.6 no
C5 . N27 . C28 . 117.8(3) yes
C5 . N27 . C29 . 120.3(3) yes
C28 . N27 . C29 . 121.8(3) yes
N27 . C28 . H281 . 110.0 no
N27 . C28 . H282 . 109.5 no
H281 . C28 . H282 . 110.4 no
N27 . C28 . H283 . 108.8 no
H281 . C28 . H283 . 109.3 no
H282 . C28 . H283 . 108.7 no
N27 . C29 . O30 . 109.3(3) yes
N27 . C29 . O35 . 123.7(4) yes
O30 . C29 . O35 . 127.0(3) yes
C29 . O30 . C31 . 119.4(3) yes
O30 . C31 . C32 . 108.8(3) yes
O30 . C31 . C33 . 102.1(3) yes
C32 . C31 . C33 . 110.5(3) yes
O30 . C31 . C34 . 110.4(3) yes
C32 . C31 . C34 . 113.6(3) yes
C33 . C31 . C34 . 110.8(3) yes
C31 . C32 . H321 . 108.6 no
C31 . C32 . H322 . 111.2 no
H321 . C32 . H322 . 109.4 no
C31 . C32 . H323 . 108.5 no
H321 . C32 . H323 . 109.7 no
H322 . C32 . H323 . 109.4 no
C31 . C33 . H331 . 109.1 no
C31 . C33 . H332 . 110.7 no
H331 . C33 . H332 . 108.3 no
C31 . C33 . H333 . 111.1 no
H331 . C33 . H333 . 109.2 no
H332 . C33 . H333 . 108.3 no
C31 . C34 . H341 . 109.4 no
C31 . C34 . H342 . 109.8 no
H341 . C34 . H342 . 109.3 no
C31 . C34 . H343 . 109.9 no
H341 . C34 . H343 . 108.5 no
H342 . C34 . H343 . 110.0 no
I101 . C102 . C103 . 118.9(2) yes
I101 . C102 . C110 . 120.8(2) yes
C103 . C102 . C110 . 120.4(3) yes
C102 . C103 . N104 . 126.0(3) yes
C102 . C103 . C107 . 118.8(3) yes
N104 . C103 . C107 . 115.2(3) yes
C103 . N104 . C105 . 109.7(3) yes
N104 . C105 . S106 . 117.5(3) yes
N104 . C105 . N127 . 120.1(3) yes
S106 . C105 . N127 . 122.3(3) yes
C105 . S106 . C107 . 87.72(16) yes
C103 . C107 . S106 . 109.8(3) yes
C103 . C107 . C108 . 121.7(3) yes
S106 . C107 . C108 . 128.4(3) yes
C107 . C108 . C109 . 118.1(3) yes
C107 . C108 . H1081 . 121.4 no
C109 . C108 . H1081 . 120.5 no
C108 . C109 . C110 . 121.7(3) yes
C108 . C109 . H1091 . 119.5 no
C110 . C109 . H1091 . 118.8 no
C109 . C110 . C102 . 119.3(3) yes
C109 . C110 . N111 . 120.3(3) yes
C102 . C110 . N111 . 120.3(3) yes
C110 . N111 . C112 . 124.8(3) yes
C110 . N111 . H1111 . 117.8 no
C112 . N111 . H1111 . 116.7 no
N111 . C112 . O113 . 125.1(3) yes
N111 . C112 . N114 . 112.2(3) yes
O113 . C112 . N114 . 122.8(3) yes
C112 . N114 . C115 . 124.7(3) yes
C112 . N114 . H1141 . 117.8 no
C115 . N114 . H1141 . 117.1 no
N114 . C115 . S116 . 122.5(3) yes
N114 . C115 . C119 . 125.9(3) yes
S116 . C115 . C119 . 111.3(3) yes
C115 . S116 . C117 . 91.90(17) yes
S116 . C117 . C118 . 110.7(3) yes
S116 . C117 . C125 . 119.3(3) yes
C118 . C117 . C125 . 130.0(3) yes
C117 . C118 . C119 . 114.3(3) yes
C117 . C118 . H1181 . 123.6 no
C119 . C118 . H1181 . 122.1 no
C118 . C119 . C115 . 111.8(3) yes
C118 . C119 . C120 . 126.4(3) yes
C115 . C119 . C120 . 121.8(3) yes
C119 . C120 . O121 . 111.7(3) yes
C119 . C120 . O124 . 124.8(3) yes
O121 . C120 . O124 . 123.5(3) yes
C120 . O121 . C122 . 115.0(3) yes
O121 . C122 . C123 . 107.9(3) yes
O121 . C122 . H1222 . 110.1 no
C123 . C122 . H1222 . 110.2 no
O121 . C122 . H1221 . 110.1 no
C123 . C122 . H1221 . 109.5 no
H1222 . C122 . H1221 . 109.0 no
C122 . C123 . H1231 . 109.7 no
C122 . C123 . H1233 . 109.6 no
H1231 . C123 . H1233 . 109.3 no
C122 . C123 . H1232 . 109.3 no
H1231 . C123 . H1232 . 109.2 no
H1233 . C123 . H1232 . 109.8 no
C117 . C125 . C126 . 113.3(3) yes
C117 . C125 . H1251 . 109.1 no
C126 . C125 . H1251 . 109.0 no
C117 . C125 . H1252 . 108.6 no
C126 . C125 . H1252 . 108.4 no
H1251 . C125 . H1252 . 108.3 no
C125 . C126 . H1261 . 110.1 no
C125 . C126 . H1262 . 110.3 no
H1261 . C126 . H1262 . 109.0 no
C125 . C126 . H1263 . 109.7 no
H1261 . C126 . H1263 . 109.1 no
H1262 . C126 . H1263 . 108.5 no
C105 . N127 . C129 . 120.3(3) yes
C105 . N127 . C128 . 116.5(3) yes
C129 . N127 . C128 . 123.2(3) yes
N127 . C129 . O130 . 111.5(3) yes
N127 . C129 . O135 . 122.5(3) yes
O130 . C129 . O135 . 126.0(3) yes
C129 . O130 . C131 . 118.5(3) yes
O130 . C131 . C134 . 110.0(3) yes
O130 . C131 . C133 . 102.4(3) yes
C134 . C131 . C133 . 110.6(3) yes
O130 . C131 . C132 . 109.7(3) yes
C134 . C131 . C132 . 112.3(3) yes
C133 . C131 . C132 . 111.4(4) yes
C131 . C134 . H1342 . 109.0 no
C131 . C134 . H1341 . 111.2 no
H1342 . C134 . H1341 . 109.4 no
C131 . C134 . H1343 . 110.1 no
H1342 . C134 . H1343 . 107.7 no
H1341 . C134 . H1343 . 109.4 no
C131 . C133 . H1332 . 109.8 no
C131 . C133 . H1331 . 110.2 no
H1332 . C133 . H1331 . 108.9 no
C131 . C133 . H1333 . 109.6 no
H1332 . C133 . H1333 . 109.3 no
H1331 . C133 . H1333 . 109.1 no
C131 . C132 . H1322 . 108.4 no
C131 . C132 . H1321 . 109.4 no
H1322 . C132 . H1321 . 109.6 no
C131 . C132 . H1323 . 110.0 no
H1322 . C132 . H1323 . 109.3 no
H1321 . C132 . H1323 . 110.1 no
N127 . C128 . H1282 . 109.3 no
N127 . C128 . H1281 . 108.4 no
H1282 . C128 . H1281 . 110.3 no
N127 . C128 . H1283 . 108.7 no
H1282 . C128 . H1283 . 109.7 no
H1281 . C128 . H1283 . 110.5 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
C108 . H1081 . O113 2_666 155.78 0.924 2.499 3.363(5) yes
N111 . H1111 . O13 1_655 156.1 0.855 2.274 3.076(5) yes
N11 . H111 . O113 . 153.1 0.859 2.283 3.073(5) yes
N14 . H141 . O24 . 121.8 0.867 2.200 2.757(5) yes
N14 . H141 . O113 . 135.4 0.867 2.552 3.227(5) yes
N114 . H1141 . O13 1_655 130.4 0.860 2.560 3.185(5) yes
N114 . H1141 . O124 . 124.4 0.860 2.192 2.771(5) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 17/09/15 at 11:30:57
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) H   ( 233,X'S) 
RIDE C   (  25,X'S) H   ( 252,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 263,X'S) H   ( 262,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) H   ( 323,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) H   ( 333,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) H   ( 343,X'S) 
RIDE C   ( 108,X'S) H   (1081,X'S) 
RIDE C   ( 109,X'S) H   (1091,X'S) 
RIDE C   ( 118,X'S) H   (1181,X'S) 
RIDE C   ( 122,X'S) H   (1222,X'S) H   (1221,X'S) 
RIDE C   ( 123,X'S) H   (1231,X'S) H   (1233,X'S) H   (1232,X'S) 
RIDE C   ( 125,X'S) H   (1251,X'S) H   (1252,X'S) 
RIDE C   ( 126,X'S) H   (1261,X'S) H   (1262,X'S) H   (1263,X'S) 
RIDE C   ( 134,X'S) H   (1342,X'S) H   (1341,X'S) H   (1343,X'S) 
RIDE C   ( 133,X'S) H   (1332,X'S) H   (1331,X'S) H   (1333,X'S) 
RIDE C   ( 132,X'S) H   (1322,X'S) H   (1321,X'S) H   (1323,X'S) 
RIDE C   ( 128,X'S) H   (1282,X'S) H   (1281,X'S) H   (1283,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 17/09/15 at 11:30:57
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
