# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_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                   11.4883(6)
_cell_length_b                   9.6632(5)
_cell_length_c                   16.1106(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.252(2)
_cell_angle_gamma                90
_cell_volume                     1754.12(16)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?
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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C34 H30 Cl2 N6 O10 S2 
# Dc =      1.55 Fooo =    844.00 Mu =      3.73 M =    408.84
# Found Formula = C34 H30 Cl2 N6 O10 S2 
# Dc =      1.55 FOOO =    844.00 Mu =      3.73 M =    408.84

_chemical_formula_sum            'C34 H30 Cl2 N6 O10 S2'
_chemical_formula_moiety         'C34 H30 Cl2 N6 O10 S2'
_chemical_compound_source        ?
_chemical_formula_weight         817.68


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.120
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.160

_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.373

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_T_max  0.9562
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      100
_diffrn_reflns_number            69747
_reflns_number_total             13661
_diffrn_reflns_av_R_equivalents  0.046
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 13661 
# Theoretical number of reflections is about 27748 


_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         44.253
_diffrn_measured_fraction_theta_max 0.982

_diffrn_reflns_theta_full        37.173
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -22
_reflns_limit_h_max              22
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   1.13
_oxford_diffrn_Wilson_scale      72.45

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.62


# 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>2.0\s(I)
_refine_ls_number_reflns         8688
_refine_ls_number_restraints     0
_refine_ls_number_parameters     244
_oxford_refine_ls_R_factor_ref   0.0427
_refine_ls_wR_factor_ref         0.0465
_refine_ls_goodness_of_fit_ref   1.0761
_refine_ls_shift/su_max          0.0015800
_refine_ls_shift/su_mean         0.0000853


# The values computed from all data 
_oxford_reflns_number_all        13651
_refine_ls_R_factor_all          0.0818
_refine_ls_wR_factor_all         0.1082

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                8688
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.0465

# 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 # none, 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: 
 0.189 0.173 0.547E-01 
;

# 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
H1 H 0.7131 1.1294 -0.2017 0.0500 1.0000 Uiso R . . . . .
H2 H 1.1052 0.9733 0.1769 0.0500 1.0000 Uiso R . . . . .
H3 H 1.0735 1.0552 0.2523 0.0500 1.0000 Uiso R . . . . .
H4 H 0.8324 1.0588 -0.0022 0.0150 1.0000 Uiso R . . . . .
H5 H 0.7768 1.4450 0.1580 0.0152 1.0000 Uiso R . . . . .
H6 H 0.6609 1.4803 -0.0537 0.0500 1.0000 Uiso R . . . . .
H7 H 0.7253 1.6398 0.0825 0.0183 1.0000 Uiso R . . . . .
H8 H 0.5983 1.5709 0.0800 0.0190 1.0000 Uiso R . . . . .
H9 H 0.6611 1.9026 0.0249 0.0246 1.0000 Uiso R . . . . .
H10 H 0.4218 1.7765 -0.1790 0.0233 1.0000 Uiso R . . . . .
H11 H 0.5176 1.9894 -0.1088 0.0254 1.0000 Uiso R . . . . .
H14 H 0.5060 1.1525 0.3954 0.0191 1.0000 Uiso R . . . . .
H15 H 0.4062 0.7918 0.4853 0.0205 1.0000 Uiso R . . . . .
H16 H 0.4088 1.0859 0.2598 0.0207 1.0000 Uiso R . . . . .
H17 H 0.3098 0.7375 0.3483 0.0234 1.0000 Uiso R . . . . .
O415 O 0.51986(7) 1.66672(8) -0.08438(5) 0.0180 1.0000 Uani . . . . . .
C9 C 0.61102(10) 1.84972(10) -0.01544(7) 0.0199 1.0000 Uani . . . . . .
C1 C 0.86064(7) 1.13331(9) 0.11719(5) 0.0121 1.0000 Uani . . . . . .
C2 C 0.84480(7) 1.25307(9) 0.16358(5) 0.0121 1.0000 Uani . . . . . .
C3 C 0.82138(7) 1.13641(9) 0.02992(5) 0.0122 1.0000 Uani . . . . . .
C4 C 0.76494(7) 1.25181(9) -0.01191(5) 0.0116 1.0000 Uani . . . . . .
C5 C 0.78798(8) 1.36821(9) 0.12489(5) 0.0127 1.0000 Uani . . . . . .
C6 C 0.74499(7) 1.37066(9) 0.03607(5) 0.0116 1.0000 Uani . . . . . .
C7 C 0.65482(9) 1.60097(9) 0.04562(6) 0.0156 1.0000 Uani . . . . . .
C8 C 0.60011(8) 1.71019(9) -0.01471(6) 0.0141 1.0000 Uani . . . . . .
C10 C 0.47949(9) 1.78305(11) -0.12968(6) 0.0188 1.0000 Uani . . . . . .
C11 C 0.53161(10) 1.89732(11) -0.09060(7) 0.0205 1.0000 Uani . . . . . .
C12 C 0.72354(7) 1.24574(9) -0.10528(5) 0.0126 1.0000 Uani . . . . . .
C13 C 0.46894(7) 0.98018(9) 0.45667(5) 0.0118 1.0000 Uani . . . . . .
C14 C 0.46793(9) 1.06818(10) 0.38771(5) 0.0157 1.0000 Uani . . . . . .
C15 C 0.40894(9) 0.85374(10) 0.44111(6) 0.0166 1.0000 Uani . . . . . .
C16 C 0.40919(9) 1.02798(11) 0.30796(6) 0.0176 1.0000 Uani . . . . . .
C17 C 0.35164(9) 0.82154(11) 0.35940(6) 0.0185 1.0000 Uani . . . . . .
S1 S 0.91599(2) 0.97650(2) 0.165336(14) 0.0140 1.0000 Uani . . . . . .
Cl1 Cl 0.89824(2) 1.26105(2) 0.271814(13) 0.0166 1.0000 Uani . . . . . .
O2 O 0.67086(7) 1.34419(8) -0.14578(4) 0.0172 1.0000 Uani . . . . . .
N1 N 0.68933(7) 1.48404(8) -0.00122(5) 0.0146 1.0000 Uani . . . . . .
O1 O 0.74660(7) 1.13057(8) -0.14126(4) 0.0169 1.0000 Uani . . . . . .
N3 N 0.35223(7) 0.90664(9) 0.29406(5) 0.0163 1.0000 Uani . . . . . .
O4 O 0.91147(8) 0.87788(8) 0.09773(5) 0.0220 1.0000 Uani . . . . . .
N2 N 1.05364(8) 0.99292(10) 0.20799(6) 0.0199 1.0000 Uani . . . . . .
O3 O 0.85134(8) 0.94850(9) 0.23129(6) 0.0234 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11907(12)
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
H1 . O1 . 0.975 no
H2 . N2 . 0.868 no
H3 . N2 . 0.927 no
H4 . C3 . 0.933 no
H5 . C5 . 0.938 no
H6 . N1 . 0.846 no
H7 . C7 . 0.980 no
H8 . C7 . 0.976 no
H9 . C9 . 0.933 no
H10 . C10 . 0.932 no
H11 . C11 . 0.941 no
H14 . C14 . 0.922 no
H15 . C15 . 0.936 no
H16 . C16 . 0.956 no
H17 . C17 . 0.943 no
O415 . C8 . 1.3721(11) yes
O415 . C10 . 1.3709(12) yes
C9 . C8 . 1.3544(13) yes
C9 . C11 . 1.4418(15) yes
C1 . C2 . 1.4086(12) yes
C1 . C3 . 1.3905(11) yes
C1 . S1 . 1.7634(8) yes
C2 . C5 . 1.3761(12) yes
C2 . Cl1 . 1.7336(8) yes
C3 . C4 . 1.3955(12) yes
C4 . C6 . 1.4277(12) yes
C4 . C12 . 1.4877(11) yes
C5 . C6 . 1.4201(11) yes
C6 . N1 . 1.3491(11) yes
C7 . C8 . 1.4883(13) yes
C7 . N1 . 1.4560(12) yes
C10 . C11 . 1.3517(15) yes
C12 . O2 . 1.2421(11) yes
C12 . O1 . 1.3055(11) yes
C13 . C13 2_676 1.4887(15) yes
C13 . C14 . 1.3974(12) yes
C13 . C15 . 1.4011(13) yes
C14 . C16 . 1.3851(12) yes
C15 . C17 . 1.3874(12) yes
C16 . N3 . 1.3402(13) yes
C17 . N3 . 1.3369(13) yes
S1 . O4 . 1.4405(8) yes
S1 . N2 . 1.6044(9) yes
S1 . O3 . 1.4359(9) yes
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
C8 . O415 . C10 . 106.73(7) yes
H9 . C9 . C8 . 125.8 no
H9 . C9 . C11 . 127.9 no
C8 . C9 . C11 . 106.28(9) yes
C2 . C1 . C3 . 117.96(7) yes
C2 . C1 . S1 . 123.05(6) yes
C3 . C1 . S1 . 118.77(6) yes
C1 . C2 . C5 . 121.52(7) yes
C1 . C2 . Cl1 . 120.88(6) yes
C5 . C2 . Cl1 . 117.59(6) yes
C1 . C3 . H4 . 119.4 no
C1 . C3 . C4 . 122.28(8) yes
H4 . C3 . C4 . 118.4 no
C3 . C4 . C6 . 119.33(7) yes
C3 . C4 . C12 . 118.92(7) yes
C6 . C4 . C12 . 121.72(7) yes
H5 . C5 . C2 . 119.2 no
H5 . C5 . C6 . 120.1 no
C2 . C5 . C6 . 120.73(8) yes
C4 . C6 . C5 . 118.11(7) yes
C4 . C6 . N1 . 121.63(7) yes
C5 . C6 . N1 . 120.24(8) yes
H7 . C7 . H8 . 109.4 no
H7 . C7 . C8 . 108.5 no
H8 . C7 . C8 . 109.8 no
H7 . C7 . N1 . 109.6 no
H8 . C7 . N1 . 110.0 no
C8 . C7 . N1 . 109.57(7) yes
C7 . C8 . O415 . 116.60(8) yes
C7 . C8 . C9 . 133.13(9) yes
O415 . C8 . C9 . 110.26(8) yes
H10 . C10 . O415 . 120.5 no
H10 . C10 . C11 . 129.0 no
O415 . C10 . C11 . 110.41(9) yes
C9 . C11 . H11 . 127.2 no
C9 . C11 . C10 . 106.31(9) yes
H11 . C11 . C10 . 126.5 no
C4 . C12 . O2 . 121.85(8) yes
C4 . C12 . O1 . 115.47(7) yes
O2 . C12 . O1 . 122.68(8) yes
C13 2_676 C13 . C14 . 121.13(10) yes
C13 2_676 C13 . C15 . 121.42(9) yes
C14 . C13 . C15 . 117.45(7) yes
C13 . C14 . H14 . 120.1 no
C13 . C14 . C16 . 119.59(9) yes
H14 . C14 . C16 . 120.3 no
C13 . C15 . H15 . 120.7 no
C13 . C15 . C17 . 119.41(8) yes
H15 . C15 . C17 . 119.9 no
H16 . C16 . C14 . 120.8 no
H16 . C16 . N3 . 116.9 no
C14 . C16 . N3 . 122.28(9) yes
H17 . C17 . C15 . 120.2 no
H17 . C17 . N3 . 117.4 no
C15 . C17 . N3 . 122.33(9) yes
C1 . S1 . O4 . 106.21(4) yes
C1 . S1 . N2 . 110.13(5) yes
O4 . S1 . N2 . 106.04(5) yes
C1 . S1 . O3 . 107.05(5) yes
O4 . S1 . O3 . 119.16(6) yes
N2 . S1 . O3 . 108.10(5) yes
C7 . N1 . C6 . 123.56(7) yes
C7 . N1 . H6 . 117.4 no
C6 . N1 . H6 . 117.9 no
H1 . O1 . C12 . 112.3 no
C16 . N3 . C17 . 118.94(8) yes
H3 . N2 . H2 . 119.5 no
H3 . N2 . S1 . 117.9 no
H2 . N2 . S1 . 117.2 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
O1 . H1 . C16 2_675 138.48 0.975 2.506 3.2997(13) yes
O1 . H1 . C17 2_675 167.24 0.975 2.549 3.5058(13) yes
O1 . H1 . N3 2_675 166.45 0.975 1.569 2.5273(13) yes
N2 . H2 . O1 2_775 157.18 0.868 2.149 2.9680(13) yes
N2 . H3 . O2 4_575 160.25 0.927 2.044 2.9332(13) yes
C5 . H5 . O3 3_655 125.17 0.938 2.525 3.1590(13) yes
N1 . H6 . O2 . 134.57 0.846 2.002 2.6650(13) yes
C14 . H14 . O4 3_655 173.74 0.922 2.369 3.2869(13) yes
C15 . H15 . O4 4_465 175.84 0.936 2.435 3.3688(13) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 05/09/12 at 15:06:03
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   9,X'S) H   (   9,X'S) 
RIDE C   (   3,X'S) H   (   4,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   7,X'S) H   (   7,X'S) H   (   8,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  17,X'S) H   (  17,X'S) 
RIDE N   (   1,X'S) H   (   6,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE N   (   2,X'S) H   (   3,X'S) H   (   2,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 05/09/12 at 15:06:03
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        'Furosemide - bipyridyl'
_database_code_depnum_ccdc_archive 'CCDC 943029'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FUS-BP-DMSO
_audit_creation_date             12-06-08
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 'x84196_0m in P-1'
_chemical_name_systematic        'Furosemide - bipyridyl-DMSO'
_chemical_melting_point          ?

# Hand-made tables can be put in the cif. The number of columns 
# is set in the loop header. 
# The contants of each column can either be a piece of text 
# without any spaces (eg a number) or other text enclosed in " " 
# Remove the leading # in the following example 

#geom_extra_table_head_A 
#; 
#Table 2. 
#Molecular parameters deviating most from MOGUL averages 
#; 
# 
#loop_ 
#_geom_extra_tableA_col_1 
#_geom_extra_tableA_col_2 
#_geom_extra_tableA_col_3 
#_geom_extra_tableA_col_4 
# 
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" 
#N5-C6-C4 129 124 "7 (\%)" 
#C3-O10-C2 105 109 "2 (\%)" 
#C6-O7 1.25 1.22 ".02 (\%A)" 
# 



_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                   9.7483(4)
_cell_length_b                   10.4805(4)
_cell_length_c                   14.1432(5)
_cell_angle_alpha                96.253(2)
_cell_angle_beta                 93.883(2)
_cell_angle_gamma                114.448(2)
_cell_volume                     1297.39(9)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C24 H29 Cl1 N4 O4 S1 
# Dc =      1.29 Fooo =    588.00 Mu =      2.64 M =    505.04
# Found Formula = C24 H25 Cl1 N4 O6 S2 
# Dc =      1.45 FOOO =    588.00 Mu =      3.56 M =    565.07

_chemical_formula_sum            'C24 H25 Cl1 N4 O6 S2'
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S, C10 H8 N2, C2 H6 O S'
_chemical_compound_source        ?
_chemical_formula_weight         565.07


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.110
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_max          0.210

_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.356

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9514
_exptl_absorpt_correction_T_max  0.9616
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      100
_diffrn_reflns_number            33521
_reflns_number_total             10086
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 10086 
# Theoretical number of reflections is about 21574 


_diffrn_reflns_theta_min         1.460
_diffrn_reflns_theta_max         34.248
_diffrn_measured_fraction_theta_max 0.934

_diffrn_reflns_theta_full        25.001
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -15
_reflns_limit_h_max              15
_reflns_limit_k_min              -16
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.64
_refine_diff_density_max         1.19


# 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>2.0\s(I)
_refine_ls_number_reflns         7440
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0446
_refine_ls_wR_factor_ref         0.0452
_refine_ls_goodness_of_fit_ref   1.1186
_refine_ls_shift/su_max          0.0009639
_refine_ls_shift/su_mean         0.0000434


# The values computed from all data 
_oxford_reflns_number_all        10067
_refine_ls_R_factor_all          0.0651
_refine_ls_wR_factor_all         0.0753

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7440
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_gt          0.0452

# 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 # none, 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: 
 0.146 0.925E-01 0.332E-01 
;

# 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
H1 H 0.1223 0.8863 1.0074 0.0500 1.0000 Uiso R . . . . .
H2 H 0.5175 1.2450 0.9941 0.0500 1.0000 Uiso R . . . . .
H3 H 0.2736 0.7981 0.8451 0.0193 1.0000 Uiso R . . . . .
H5 H 0.7191 1.1914 0.8173 0.0222 1.0000 Uiso R . . . . .
H6 H 0.3816 0.7409 0.5607 0.0500 1.0000 Uiso R . . . . .
H7 H 0.2425 0.7122 0.6055 0.0500 1.0000 Uiso R . . . . .
H8 H 0.7970 1.3166 0.9753 0.0296 1.0000 Uiso R . . . . .
H9 H 0.7386 1.4138 1.0339 0.0296 1.0000 Uiso R . . . . .
H10 H 0.9648 1.4559 0.8459 0.0388 1.0000 Uiso R . . . . .
H11 H 0.9444 1.6600 0.7561 0.0706 1.0000 Uiso R . . . . .
H12 H 0.7266 1.6910 0.8053 0.0686 1.0000 Uiso R . . . . .
H13 H 0.3688 0.6059 0.3628 0.0291 1.0000 Uiso R . . . . .
H14 H 0.6187 0.9986 0.4814 0.0276 1.0000 Uiso R . . . . .
H15 H 0.7936 1.0261 0.3741 0.0242 1.0000 Uiso R . . . . .
H16 H 0.5336 0.6201 0.2497 0.0250 1.0000 Uiso R . . . . .
H19 H 0.7213 0.6304 0.1759 0.0336 1.0000 Uiso R . . . . .
H20 H 0.9133 1.0561 0.2576 0.0250 1.0000 Uiso R . . . . .
H21 H 1.0805 1.0750 0.1453 0.0255 1.0000 Uiso R . . . . .
H22 H 0.8910 0.6634 0.0639 0.0365 1.0000 Uiso R . . . . .
H23 H 0.0097 0.2366 0.5923 0.0500 1.0000 Uiso R . . . . .
H24 H -0.0700 0.3307 0.5939 0.0500 1.0000 Uiso R . . . . .
H25 H 0.0972 0.3888 0.6355 0.0500 1.0000 Uiso R . . . . .
H26 H 0.2179 0.2493 0.4887 0.0500 1.0000 Uiso R . . . . .
H27 H 0.3254 0.3968 0.5280 0.0500 1.0000 Uiso R . . . . .
H28 H 0.2813 0.3493 0.4194 0.0500 1.0000 Uiso R . . . . .
S1 S 0.39570(4) 0.69510(4) 0.70295(2) 0.0188 1.0000 Uani . . . . . .
S2 S 0.07960(4) 0.37381(4) 0.47527(3) 0.0186 1.0000 Uani . . . . . .
N1 N 0.31389(14) 0.69605(13) 0.60055(9) 0.0205 1.0000 Uani . . . . . .
N2 N 0.57489(15) 1.24961(13) 0.95227(9) 0.0225 1.0000 Uani . . . . . .
N3 N 0.47800(16) 0.79951(15) 0.43383(9) 0.0234 1.0000 Uani . . . . . .
N4 N 1.00006(14) 0.87157(13) 0.09464(9) 0.0200 1.0000 Uani . . . . . .
O1 O 0.17746(12) 0.88552(11) 0.96713(8) 0.0207 1.0000 Uani . . . . . .
O2 O 0.31357(12) 1.11544(11) 1.02490(8) 0.0216 1.0000 Uani . . . . . .
O3 O 0.28031(15) 0.59853(12) 0.75146(8) 0.0268 1.0000 Uani . . . . . .
O4 O 0.52463(15) 0.66712(13) 0.68521(9) 0.0300 1.0000 Uani . . . . . .
O5 O 0.69490(17) 1.53730(15) 0.88957(12) 0.0438 1.0000 Uani . . . . . .
O6 O -0.03860(13) 0.25932(12) 0.40116(8) 0.0257 1.0000 Uani . . . . . .
C1 C 0.45671(15) 0.86387(15) 0.77273(9) 0.0168 1.0000 Uani . . . . . .
C2 C 0.58841(15) 0.98479(15) 0.76491(9) 0.0174 1.0000 Uani . . . . . .
C3 C 0.36435(15) 0.87830(14) 0.83963(9) 0.0160 1.0000 Uani . . . . . .
C4 C 0.39914(15) 1.00550(14) 0.89913(9) 0.0155 1.0000 Uani . . . . . .
C5 C 0.62818(16) 1.11195(15) 0.82367(10) 0.0185 1.0000 Uani . . . . . .
C6 C 0.53570(15) 1.12568(14) 0.89307(9) 0.0173 1.0000 Uani . . . . . .
C7 C 0.29395(15) 1.00878(15) 0.96969(10) 0.0172 1.0000 Uani . . . . . .
C8 C 0.72944(18) 1.36082(16) 0.97297(11) 0.0247 1.0000 Uani . . . . . .
C9 C 0.77590(17) 1.46194(15) 0.90204(11) 0.0226 1.0000 Uani . . . . . .
C10 C 0.8927(2) 1.4948(2) 0.84988(13) 0.0323 1.0000 Uani . . . . . .
C11 C 0.8796(3) 1.6093(2) 0.79942(15) 0.0588 1.0000 Uani . . . . . .
C12 C 0.7613(3) 1.6254(2) 0.8269(2) 0.0571 1.0000 Uani . . . . . .
C13 C 0.45657(18) 0.69237(17) 0.36513(11) 0.0242 1.0000 Uani . . . . . .
C14 C 0.60197(18) 0.92028(16) 0.43418(11) 0.0230 1.0000 Uani . . . . . .
C15 C 0.70716(17) 0.93807(15) 0.36990(10) 0.0202 1.0000 Uani . . . . . .
C16 C 0.55482(17) 0.69968(15) 0.29699(10) 0.0208 1.0000 Uani . . . . . .
C17 C 0.68481(15) 0.82520(14) 0.29885(9) 0.0161 1.0000 Uani . . . . . .
C18 C 0.79517(15) 0.84049(14) 0.22881(9) 0.0156 1.0000 Uani . . . . . .
C19 C 0.7927(2) 0.72336(16) 0.17041(13) 0.0280 1.0000 Uani . . . . . .
C20 C 0.90605(16) 0.97326(15) 0.21857(11) 0.0208 1.0000 Uani . . . . . .
C21 C 1.00547(16) 0.98385(15) 0.15124(11) 0.0212 1.0000 Uani . . . . . .
C22 C 0.8953(2) 0.74390(17) 0.10425(13) 0.0304 1.0000 Uani . . . . . .
C23 C 0.0224(2) 0.3274(2) 0.58872(12) 0.0309 1.0000 Uani . . . . . .
C24 C 0.2433(2) 0.3378(2) 0.48059(14) 0.0309 1.0000 Uani . . . . . .
Cl1 Cl 0.70703(4) 0.98190(4) 0.67937(3) 0.0260 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.14723(15)
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
H1 . O1 . 0.812 no
H2 . N2 . 0.833 no
H3 . C3 . 0.950 no
H5 . C5 . 0.950 no
H6 . N1 . 0.909 no
H7 . N1 . 0.787 no
H8 . C8 . 0.950 no
H9 . C8 . 0.950 no
H10 . C10 . 0.950 no
H11 . C11 . 0.950 no
H12 . C12 . 0.950 no
H13 . C13 . 0.950 no
H14 . C14 . 0.950 no
H15 . C15 . 0.950 no
H16 . C16 . 0.950 no
H19 . C19 . 0.950 no
H20 . C20 . 0.950 no
H21 . C21 . 0.950 no
H22 . C22 . 0.950 no
H23 . C23 . 0.915 no
H24 . C23 . 0.923 no
H25 . C23 . 0.914 no
H26 . C24 . 0.879 no
H27 . C24 . 0.948 no
H28 . C24 . 0.965 no
S1 . N1 . 1.6083(13) yes
S1 . O3 . 1.4401(12) yes
S1 . O4 . 1.4354(12) yes
S1 . C1 . 1.7679(14) yes
S2 . O6 . 1.5113(11) yes
S2 . C23 . 1.7855(17) yes
S2 . C24 . 1.7844(16) yes
N2 . C6 . 1.3576(18) yes
N2 . C8 . 1.4582(19) yes
N3 . C13 . 1.338(2) yes
N3 . C14 . 1.339(2) yes
N4 . C21 . 1.3290(19) yes
N4 . C22 . 1.334(2) yes
O1 . C7 . 1.3152(17) yes
O2 . C7 . 1.2282(17) yes
O5 . C9 . 1.344(2) yes
O5 . C12 . 1.349(3) yes
C1 . C2 . 1.4034(19) yes
C1 . C3 . 1.3878(18) yes
C2 . C5 . 1.380(2) yes
C2 . Cl1 . 1.7355(14) yes
C3 . C4 . 1.3939(18) yes
C4 . C6 . 1.4203(18) yes
C4 . C7 . 1.4862(19) yes
C5 . C6 . 1.4118(19) yes
C8 . C9 . 1.494(2) yes
C9 . C10 . 1.343(2) yes
C10 . C11 . 1.506(3) yes
C11 . C12 . 1.310(4) yes
C13 . C16 . 1.390(2) yes
C14 . C15 . 1.385(2) yes
C15 . C17 . 1.3980(19) yes
C16 . C17 . 1.3947(19) yes
C17 . C18 . 1.4835(19) yes
C18 . C19 . 1.393(2) yes
C18 . C20 . 1.3948(19) yes
C19 . C22 . 1.384(2) yes
C20 . C21 . 1.385(2) yes
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
N1 . S1 . O3 . 106.81(7) yes
N1 . S1 . O4 . 107.13(7) yes
O3 . S1 . O4 . 118.37(8) yes
N1 . S1 . C1 . 108.78(7) yes
O3 . S1 . C1 . 105.61(7) yes
O4 . S1 . C1 . 109.82(7) yes
O6 . S2 . C23 . 105.59(8) yes
O6 . S2 . C24 . 106.51(8) yes
C23 . S2 . C24 . 98.16(9) yes
H6 . N1 . S1 . 112.4 no
H6 . N1 . H7 . 119.5 no
S1 . N1 . H7 . 112.1 no
H2 . N2 . C6 . 114.2 no
H2 . N2 . C8 . 116.9 no
C6 . N2 . C8 . 123.74(13) yes
C13 . N3 . C14 . 116.28(13) yes
C21 . N4 . C22 . 118.25(13) yes
H1 . O1 . C7 . 113.1 no
C9 . O5 . C12 . 106.65(19) yes
S1 . C1 . C2 . 125.70(10) yes
S1 . C1 . C3 . 116.93(10) yes
C2 . C1 . C3 . 117.35(12) yes
C1 . C2 . C5 . 121.62(12) yes
C1 . C2 . Cl1 . 121.43(11) yes
C5 . C2 . Cl1 . 116.95(10) yes
H3 . C3 . C1 . 118.6 no
H3 . C3 . C4 . 118.6 no
C1 . C3 . C4 . 122.75(12) yes
C3 . C4 . C6 . 119.35(12) yes
C3 . C4 . C7 . 118.43(12) yes
C6 . C4 . C7 . 122.18(12) yes
H5 . C5 . C2 . 119.5 no
H5 . C5 . C6 . 119.5 no
C2 . C5 . C6 . 120.94(12) yes
C4 . C6 . C5 . 117.94(12) yes
C4 . C6 . N2 . 120.62(13) yes
C5 . C6 . N2 . 121.45(13) yes
C4 . C7 . O1 . 113.09(12) yes
C4 . C7 . O2 . 123.60(13) yes
O1 . C7 . O2 . 123.31(13) yes
N2 . C8 . H9 . 108.0 no
N2 . C8 . H8 . 108.0 no
H9 . C8 . H8 . 109.5 no
N2 . C8 . C9 . 115.32(13) yes
H9 . C8 . C9 . 108.0 no
H8 . C8 . C9 . 108.0 no
C8 . C9 . O5 . 117.06(15) yes
C8 . C9 . C10 . 129.64(16) yes
O5 . C9 . C10 . 113.24(16) yes
H10 . C10 . C9 . 129.0 no
H10 . C10 . C11 . 129.0 no
C9 . C10 . C11 . 101.96(19) yes
C10 . C11 . H11 . 126.7 no
C10 . C11 . C12 . 106.63(18) yes
H11 . C11 . C12 . 126.7 no
H12 . C12 . O5 . 124.3 no
H12 . C12 . C11 . 124.2 no
O5 . C12 . C11 . 111.5(2) yes
H13 . C13 . N3 . 118.0 no
H13 . C13 . C16 . 118.0 no
N3 . C13 . C16 . 124.07(14) yes
H14 . C14 . N3 . 118.0 no
H14 . C14 . C15 . 118.0 no
N3 . C14 . C15 . 124.09(14) yes
H15 . C15 . C14 . 120.3 no
H15 . C15 . C17 . 120.3 no
C14 . C15 . C17 . 119.32(13) yes
H16 . C16 . C13 . 120.4 no
H16 . C16 . C17 . 120.4 no
C13 . C16 . C17 . 119.22(14) yes
C15 . C17 . C16 . 117.01(12) yes
C15 . C17 . C18 . 120.77(12) yes
C16 . C17 . C18 . 122.21(12) yes
C17 . C18 . C19 . 121.63(12) yes
C17 . C18 . C20 . 121.26(12) yes
C19 . C18 . C20 . 117.11(13) yes
H19 . C19 . C18 . 120.4 no
H19 . C19 . C22 . 120.3 no
C18 . C19 . C22 . 119.29(14) yes
H20 . C20 . C18 . 120.1 no
H20 . C20 . C21 . 120.1 no
C18 . C20 . C21 . 119.71(13) yes
H21 . C21 . C20 . 118.7 no
H21 . C21 . N4 . 118.7 no
C20 . C21 . N4 . 122.62(13) yes
H22 . C22 . C19 . 118.5 no
H22 . C22 . N4 . 118.5 no
C19 . C22 . N4 . 123.00(14) yes
S2 . C23 . H24 . 108.7 no
S2 . C23 . H23 . 109.8 no
H24 . C23 . H23 . 107.9 no
S2 . C23 . H25 . 108.0 no
H24 . C23 . H25 . 112.8 no
H23 . C23 . H25 . 109.6 no
S2 . C24 . H28 . 107.4 no
S2 . C24 . H27 . 116.6 no
H28 . C24 . H27 . 106.8 no
S2 . C24 . H26 . 110.1 no
H28 . C24 . H26 . 107.5 no
H27 . C24 . H26 . 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
O1 . H1 . N4 1_456 174.70 0.812 1.747 2.556(2) yes
N2 . H2 . O2 . 139.56 0.833 2.000 2.688(2) yes
N1 . H6 . N3 . 160.92 0.909 2.114 2.988(2) yes
N1 . H7 . O6 2_566 172.02 0.787 2.126 2.908(2) yes
C8 . H8 . O1 2_677 141.03 0.950 2.449 3.243(2) yes
C11 . H11 . O6 2_676 160.18 0.950 2.559 3.468(2) yes
C12 . H12 . O4 1_565 133.19 0.950 2.423 3.151(2) yes
C15 . H15 . O6 1_665 165.36 0.950 2.280 3.209(2) yes
C23 . H25 . O3 . 166.42 0.914 2.506 3.402(2) yes
C24 . H28 . O4 2_666 146.95 0.965 2.527 3.377(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/06/12 at 13:04:08
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE N   (   1,X'S) H   (   6,X'S) H   (   7,X'S) 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   8,X'S) H   (   9,X'S) H   (   8,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
RIDE C   (  21,X'S) H   (  21,X'S) 
RIDE C   (  22,X'S) H   (  22,X'S) 
RIDE C   (  23,X'S) H   (  24,X'S) H   (  23,X'S) H   (  25,X'S) 
RIDE C   (  24,X'S) H   (  28,X'S) H   (  27,X'S) H   (  26,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/06/12 at 13:04:08
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 943030'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FUS-BP-MeOH

_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                   7.3552(9)
_cell_length_b                   9.3457(11)
_cell_length_c                   18.124(2)
_cell_angle_alpha                80.525(6)
_cell_angle_beta                 82.376(6)
_cell_angle_gamma                75.758(6)
_cell_volume                     1185.5(2)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C22 H18 Cl1 N4 O6 S1 
# Dc =      1.41 Fooo =    540.00 Mu =      2.95 M =    501.93
# Found Formula = C23 H23 Cl1 N4 O6 S1 
# Dc =      1.45 FOOO =    540.00 Mu =      2.97 M =    518.98

_chemical_formula_sum            'C23 H23 Cl1 N4 O6 S1'
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S, C10 H8 N2, C H4 O '
_chemical_compound_source        ?
_chemical_formula_weight         518.98


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.140
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             540
_exptl_absorpt_coefficient_mu    0.297

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9592
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      293
_diffrn_reflns_number            38717
_reflns_number_total             12046
_diffrn_reflns_av_R_equivalents  0.031
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 12046 
# Theoretical number of reflections is about 28699 


_diffrn_reflns_theta_min         1.144
_diffrn_reflns_theta_max         39.815
_diffrn_measured_fraction_theta_max 0.829

_diffrn_reflns_theta_full        25.084
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -14
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.43
_refine_diff_density_max         0.64


# 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>2.0\s(I)
_refine_ls_number_reflns         9112
_refine_ls_number_restraints     0
_refine_ls_number_parameters     316
_oxford_refine_ls_R_factor_ref   0.0417
_refine_ls_wR_factor_ref         0.0447
_refine_ls_goodness_of_fit_ref   1.0771
_refine_ls_shift/su_max          0.0013569
_refine_ls_shift/su_mean         0.0000632


# The values computed from all data 
_oxford_reflns_number_all        12030
_refine_ls_R_factor_all          0.0604
_refine_ls_wR_factor_all         0.0601

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9112
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_gt          0.0447

# 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 # none, 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: 
 0.351 0.288 0.183 
;

# 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
H18 H 1.0574 1.0623 0.5865 0.0464 1.0000 Uiso R . . . . .
H23 H 0.8889 1.0607 0.6477 0.0464 1.0000 Uiso R . . . . .
H24 H 0.8687 1.0400 0.5662 0.0464 1.0000 Uiso R . . . . .
N3 N 0.37117(15) 0.33445(12) 0.51338(5) 0.0207 1.0000 Uani . . . . . .
N4 N -0.09539(12) 0.36748(9) 0.88275(4) 0.0129 1.0000 Uani . . . . . .
H25 H 0.9104 0.8446 0.6365 0.0500 1.0000 Uiso R . . . . .
H1 H 0.2238 0.6139 1.0235 0.0500 1.0000 Uiso R . . . . .
H2 H 0.3708 0.2061 0.9518 0.0500 1.0000 Uiso R . . . . .
H3 H 0.3857 0.6812 0.8558 0.0142 1.0000 Uiso R . . . . .
H5 H 0.5772 0.2144 0.7716 0.0145 1.0000 Uiso R . . . . .
H6 H 0.4725 0.7132 0.5940 0.0500 1.0000 Uiso R . . . . .
H7 H 0.2929 0.7793 0.6315 0.0500 1.0000 Uiso R . . . . .
H8 H 0.4168 0.0521 0.8408 0.0173 1.0000 Uiso R . . . . .
H9 H 0.4054 -0.0180 0.9246 0.0173 1.0000 Uiso R . . . . .
H10 H 0.7597 -0.0695 0.7692 0.0219 1.0000 Uiso R . . . . .
H11 H 1.0863 -0.1822 0.8181 0.0262 1.0000 Uiso R . . . . .
H12 H 1.0485 -0.1578 0.9533 0.0261 1.0000 Uiso R . . . . .
H13 H -0.1006 0.5835 0.8584 0.0171 1.0000 Uiso R . . . . .
H14 H -0.0593 0.1494 0.8859 0.0179 1.0000 Uiso R . . . . .
H15 H 0.0955 0.1297 0.7663 0.0169 1.0000 Uiso R . . . . .
H16 H 0.0555 0.5768 0.7378 0.0165 1.0000 Uiso R . . . . .
H26 H 0.3360 0.1269 0.6757 0.0194 1.0000 Uiso R . . . . .
H20 H 0.0720 0.5594 0.6160 0.0230 1.0000 Uiso R . . . . .
H21 H 0.2312 0.5450 0.4968 0.0283 1.0000 Uiso R . . . . .
H22 H 0.4802 0.1249 0.5536 0.0223 1.0000 Uiso R . . . . .
S1 S 0.51726(3) 0.74463(2) 0.703764(12) 0.0115 1.0000 Uani . . . . . .
N1 N 0.41754(12) 0.75673(10) 0.62903(4) 0.0155 1.0000 Uani . . . . . .
N2 N 0.42473(12) 0.19247(9) 0.91013(4) 0.0128 1.0000 Uani . . . . . .
O1 O 0.28326(11) 0.61391(8) 0.98424(4) 0.0139 1.0000 Uani . . . . . .
O2 O 0.26392(12) 0.37510(9) 1.01080(4) 0.0179 1.0000 Uani . . . . . .
O3 O 0.71559(11) 0.73548(9) 0.68036(4) 0.0168 1.0000 Uani . . . . . .
O4 O 0.41414(12) 0.86446(8) 0.74468(4) 0.0166 1.0000 Uani . . . . . .
O5 O 0.76792(11) -0.05664(8) 0.94184(4) 0.0165 1.0000 Uani . . . . . .
O6 O 1.01535(14) 0.86426(12) 0.62245(8) 0.0351 1.0000 Uani . . . . . .
C1 C 0.49722(12) 0.57838(10) 0.76383(5) 0.0109 1.0000 Uani . . . . . .
C2 C 0.55809(12) 0.43582(10) 0.74126(4) 0.0106 1.0000 Uani . . . . . .
C3 C 0.42167(12) 0.58656(10) 0.83846(5) 0.0111 1.0000 Uani . . . . . .
C4 C 0.39727(12) 0.46046(10) 0.88858(4) 0.0101 1.0000 Uani . . . . . .
C5 C 0.53541(13) 0.30846(10) 0.78907(5) 0.0114 1.0000 Uani . . . . . .
C6 C 0.45123(12) 0.31683(10) 0.86379(4) 0.0104 1.0000 Uani . . . . . .
C7 C 0.30959(13) 0.47803(10) 0.96664(5) 0.0114 1.0000 Uani . . . . . .
C8 C 0.46614(13) 0.04429(10) 0.88765(5) 0.0135 1.0000 Uani . . . . . .
C9 C 0.67241(13) -0.02835(10) 0.87873(5) 0.0132 1.0000 Uani . . . . . .
C10 C 0.79139(15) -0.07639(12) 0.81927(6) 0.0174 1.0000 Uani . . . . . .
C11 C 0.97297(16) -0.13930(12) 0.84641(7) 0.0210 1.0000 Uani . . . . . .
C12 C 0.95105(16) -0.12524(12) 0.92042(7) 0.0208 1.0000 Uani . . . . . .
C13 C -0.06033(14) 0.49061(11) 0.83915(5) 0.0137 1.0000 Uani . . . . . .
C14 C -0.03635(14) 0.23720(11) 0.85508(5) 0.0143 1.0000 Uani . . . . . .
C15 C 0.05684(14) 0.22414(10) 0.78377(5) 0.0133 1.0000 Uani . . . . . .
C16 C 0.03232(14) 0.48761(10) 0.76705(5) 0.0132 1.0000 Uani . . . . . .
C17 C 0.09208(12) 0.35207(10) 0.73763(5) 0.0108 1.0000 Uani . . . . . .
C18 C 0.18760(13) 0.34444(10) 0.66048(5) 0.0120 1.0000 Uani . . . . . .
C19 C 0.31128(14) 0.21458(11) 0.63998(5) 0.0154 1.0000 Uani . . . . . .
C20 C 0.15669(16) 0.46877(12) 0.60493(5) 0.0184 1.0000 Uani . . . . . .
C21 C 0.25218(18) 0.45858(13) 0.53353(6) 0.0226 1.0000 Uani . . . . . .
C22 C 0.39716(15) 0.21500(12) 0.56668(5) 0.0178 1.0000 Uani . . . . . .
C23 C 0.9526(2) 1.01943(18) 0.60422(11) 0.0386 1.0000 Uani . . . . . .
Cl1 Cl 0.66707(3) 0.41261(3) 0.651583(11) 0.0140 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2955(3)
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
H18 . C23 . 0.950 no
H23 . C23 . 0.950 no
H24 . C23 . 0.950 no
N3 . C21 . 1.3417(15) yes
N3 . C22 . 1.3435(15) yes
N4 . C13 . 1.3445(12) yes
N4 . C14 . 1.3438(12) yes
H25 . O6 . 0.834 no
H1 . O1 . 0.784 no
H2 . N2 . 0.820 no
H3 . C3 . 0.952 no
H5 . C5 . 0.949 no
H6 . N1 . 0.817 no
H7 . N1 . 0.885 no
H8 . C8 . 0.952 no
H9 . C8 . 0.952 no
H10 . C10 . 0.954 no
H11 . C11 . 0.953 no
H12 . C12 . 0.953 no
H13 . C13 . 0.953 no
H14 . C14 . 0.952 no
H15 . C15 . 0.951 no
H16 . C16 . 0.952 no
H26 . C19 . 0.952 no
H20 . C20 . 0.953 no
H21 . C21 . 0.953 no
H22 . C22 . 0.955 no
S1 . N1 . 1.5993(9) yes
S1 . O3 . 1.4497(8) yes
S1 . O4 . 1.4442(8) yes
S1 . C1 . 1.7703(9) yes
N2 . C6 . 1.3568(12) yes
N2 . C8 . 1.4566(12) yes
O1 . C7 . 1.3221(11) yes
O2 . C7 . 1.2301(11) yes
O5 . C9 . 1.3763(12) yes
O5 . C12 . 1.3764(14) yes
O6 . C23 . 1.4067(19) yes
C1 . C2 . 1.4072(12) yes
C1 . C3 . 1.3993(12) yes
C2 . C5 . 1.3839(12) yes
C2 . Cl1 . 1.7366(8) yes
C3 . C4 . 1.3980(12) yes
C4 . C6 . 1.4318(12) yes
C4 . C7 . 1.4922(11) yes
C5 . C6 . 1.4184(12) yes
C8 . C9 . 1.5010(13) yes
C9 . C10 . 1.3581(13) yes
C10 . C11 . 1.4367(17) yes
C11 . C12 . 1.3537(18) yes
C13 . C16 . 1.3925(13) yes
C14 . C15 . 1.3895(12) yes
C15 . C17 . 1.4006(13) yes
C16 . C17 . 1.4030(13) yes
C17 . C18 . 1.4837(12) yes
C18 . C19 . 1.3979(14) yes
C18 . C20 . 1.4003(13) yes
C19 . C22 . 1.3930(13) yes
C20 . C21 . 1.3940(14) yes
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
C21 . N3 . C22 . 116.36(9) yes
C13 . N4 . C14 . 117.93(8) yes
N1 . S1 . O3 . 106.51(5) yes
N1 . S1 . O4 . 108.07(5) yes
O3 . S1 . O4 . 118.57(5) yes
N1 . S1 . C1 . 110.23(5) yes
O3 . S1 . C1 . 107.84(5) yes
O4 . S1 . C1 . 105.53(4) yes
H7 . N1 . H6 . 116.0 no
H7 . N1 . S1 . 119.0 no
H6 . N1 . S1 . 120.8 no
H2 . N2 . C6 . 115.6 no
H2 . N2 . C8 . 119.5 no
C6 . N2 . C8 . 124.46(8) yes
H1 . O1 . C7 . 106.1 no
C9 . O5 . C12 . 106.48(8) yes
H25 . O6 . C23 . 97.8 no
S1 . C1 . C2 . 123.48(6) yes
S1 . C1 . C3 . 119.14(7) yes
C2 . C1 . C3 . 117.35(8) yes
C1 . C2 . C5 . 121.96(8) yes
C1 . C2 . Cl1 . 120.96(6) yes
C5 . C2 . Cl1 . 117.08(7) yes
H3 . C3 . C1 . 118.9 no
H3 . C3 . C4 . 118.8 no
C1 . C3 . C4 . 122.32(8) yes
C3 . C4 . C6 . 119.70(7) yes
C3 . C4 . C7 . 119.45(8) yes
C6 . C4 . C7 . 120.82(7) yes
H5 . C5 . C2 . 119.5 no
H5 . C5 . C6 . 119.7 no
C2 . C5 . C6 . 120.84(8) yes
C4 . C6 . C5 . 117.69(8) yes
C4 . C6 . N2 . 121.41(7) yes
C5 . C6 . N2 . 120.89(8) yes
C4 . C7 . O1 . 114.44(7) yes
C4 . C7 . O2 . 122.87(8) yes
O1 . C7 . O2 . 122.69(8) yes
N2 . C8 . H8 . 108.4 no
N2 . C8 . H9 . 108.7 no
H8 . C8 . H9 . 109.1 no
N2 . C8 . C9 . 114.14(8) yes
H8 . C8 . C9 . 108.2 no
H9 . C8 . C9 . 108.3 no
C8 . C9 . O5 . 117.03(8) yes
C8 . C9 . C10 . 132.98(9) yes
O5 . C9 . C10 . 109.99(9) yes
H10 . C10 . C9 . 126.3 no
H10 . C10 . C11 . 126.9 no
C9 . C10 . C11 . 106.76(10) yes
C10 . C11 . H11 . 127.0 no
C10 . C11 . C12 . 106.17(9) yes
H11 . C11 . C12 . 126.8 no
H12 . C12 . O5 . 124.4 no
H12 . C12 . C11 . 125.0 no
O5 . C12 . C11 . 110.59(10) yes
H13 . C13 . N4 . 118.7 no
H13 . C13 . C16 . 118.8 no
N4 . C13 . C16 . 122.55(9) yes
H14 . C14 . N4 . 118.4 no
H14 . C14 . C15 . 118.3 no
N4 . C14 . C15 . 123.30(8) yes
H15 . C15 . C14 . 120.5 no
H15 . C15 . C17 . 120.3 no
C14 . C15 . C17 . 119.17(8) yes
H16 . C16 . C13 . 120.3 no
H16 . C16 . C17 . 120.0 no
C13 . C16 . C17 . 119.67(8) yes
C16 . C17 . C15 . 117.38(8) yes
C16 . C17 . C18 . 121.40(8) yes
C15 . C17 . C18 . 121.22(8) yes
C17 . C18 . C19 . 122.02(8) yes
C17 . C18 . C20 . 120.76(8) yes
C19 . C18 . C20 . 117.22(8) yes
H26 . C19 . C18 . 120.3 no
H26 . C19 . C22 . 120.5 no
C18 . C19 . C22 . 119.18(9) yes
H20 . C20 . C18 . 120.3 no
H20 . C20 . C21 . 120.5 no
C18 . C20 . C21 . 119.19(10) yes
H21 . C21 . C20 . 118.0 no
H21 . C21 . N3 . 118.1 no
C20 . C21 . N3 . 123.98(10) yes
H22 . C22 . C19 . 118.0 no
H22 . C22 . N3 . 118.0 no
C19 . C22 . N3 . 124.06(10) yes
O6 . C23 . H23 . 109.4 no
O6 . C23 . H18 . 109.6 no
H23 . C23 . H18 . 109.5 no
O6 . C23 . H24 . 109.4 no
H23 . C23 . H24 . 109.5 no
H18 . C23 . H24 . 109.5 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
O6 . H25 . O3 . 161.44 0.834 1.969 2.7725(14) yes
O1 . H1 . N4 2_567 173.25 0.784 1.844 2.6242(14) yes
N2 . H2 . O2 . 138.55 0.820 1.994 2.6647(14) yes
N2 . H2 . O5 2_657 136.27 0.820 2.449 3.0939(14) yes
N1 . H6 . N3 2_666 162.45 0.817 2.179 2.9684(14) yes
N1 . H7 . O6 1_455 169.06 0.885 2.018 2.8924(14) yes
C12 . H12 . O1 1_645 136.12 0.953 2.428 3.1846(14) yes
C13 . H13 . O2 2_567 126.40 0.953 2.556 3.2142(14) yes
C14 . H14 . O5 1_455 158.27 0.952 2.563 3.4654(14) yes
C14 . H14 . C12 1_455 156.59 0.952 2.524 3.4189(14) yes
C19 . H26 . O4 1_545 167.11 0.952 2.529 3.4639(14) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 19/06/12 at 13:02:34
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE N   (   1,X'S) H   (   7,X'S) H   (   6,X'S) 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE O   (   6,X'S) H   (  25,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   8,X'S) H   (   8,X'S) H   (   9,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  19,X'S) H   (  26,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
RIDE C   (  21,X'S) H   (  21,X'S) 
RIDE C   (  22,X'S) H   (  22,X'S) 
RIDE C   (  23,X'S) H   (  23,X'S) H   (  18,X'S) H   (  24,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 19/06/12 at 13:02:34
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        'Furosemide - bipyridyl-MeOH'
_database_code_depnum_ccdc_archive 'CCDC 943031'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FUS-BP-EG
_audit_creation_date             12-06-08
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 'x84195_0m in P-1'
_chemical_name_systematic        'Furosemide - bipyridyl-Eg'
_chemical_melting_point          ?

# Hand-made tables can be put in the cif. The number of columns 
# is set in the loop header. 
# The contants of each column can either be a piece of text 
# without any spaces (eg a number) or other text enclosed in " " 
# Remove the leading # in the following example 

#geom_extra_table_head_A 
#; 
#Table 2. 
#Molecular parameters deviating most from MOGUL averages 
#; 
# 
#loop_ 
#_geom_extra_tableA_col_1 
#_geom_extra_tableA_col_2 
#_geom_extra_tableA_col_3 
#_geom_extra_tableA_col_4 
# 
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" 
#N5-C6-C4 129 124 "7 (\%)" 
#C3-O10-C2 105 109 "2 (\%)" 
#C6-O7 1.25 1.22 ".02 (\%A)" 
# 


_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                   6.7510(5)
_cell_length_b                   9.5719(6)
_cell_length_c                   18.6178(13)
_cell_angle_alpha                84.977(4)
_cell_angle_beta                 89.783(4)
_cell_angle_gamma                73.488(4)
_cell_volume                     1148.76(14)

_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 0.0033 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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C24 H30 Cl1 N4 O4 S1 
# Dc =      1.46 Fooo =    538.00 Mu =      2.98 M =    506.05
# Found Formula = C23 H22 Cl1 N4 O6 S1 
# Dc =      1.50 FOOO =    538.00 Mu =      3.07 M =    517.97

_chemical_formula_sum            'C23 H22 Cl1 N4 O6 S1'
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S, C10 H8 N2, 0.5(C2 H6 O2)'
_chemical_compound_source        ?
_chemical_formula_weight         517.97


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.080
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_max          0.180

_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             538
_exptl_absorpt_coefficient_mu    0.307

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9758
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      100
_diffrn_reflns_number            8592
_reflns_number_total             8592
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 8592 
# Theoretical number of reflections is about 18591 


_diffrn_reflns_theta_min         1.098
_diffrn_reflns_theta_max         33.895
_diffrn_measured_fraction_theta_max 0.925

_diffrn_reflns_theta_full        25.082
_diffrn_measured_fraction_theta_full 0.980


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              -14
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.73
_refine_diff_density_max         0.98


# 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>2.0\s(I)
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_number_parameters     319
_oxford_refine_ls_R_factor_ref   0.0673
_refine_ls_wR_factor_ref         0.0640
_refine_ls_goodness_of_fit_ref   0.9645
_refine_ls_shift/su_max          0.0007181
_refine_ls_shift/su_mean         0.0000279


# The values computed from all data 
_oxford_reflns_number_all        8569
_refine_ls_R_factor_all          0.0882
_refine_ls_wR_factor_all         0.0913

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6368
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_gt          0.0640

# 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 # none, 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: 
 0.479 0.541 0.207 
;

# 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
H1 H 0.2443 1.1307 0.0535 0.0500 1.0000 Uiso R . . . . .
H2 H 0.3896 0.7190 0.1677 0.0500 1.0000 Uiso R . . . . .
H3 H 0.2040 1.1826 0.2248 0.0144 1.0000 Uiso R . . . . .
H5 H 0.4069 0.7169 0.3500 0.0141 1.0000 Uiso R . . . . .
H6 H 0.1086 1.1962 0.4764 0.0500 1.0000 Uiso R . . . . .
H7 H -0.0599 1.3143 0.4214 0.0500 1.0000 Uiso R . . . . .
H8 H 0.5759 0.5416 0.2770 0.0190 1.0000 Uiso R . . . . .
H9 H 0.3563 0.5260 0.2649 0.0190 1.0000 Uiso R . . . . .
H10 H 0.8628 0.3623 0.1915 0.0298 1.0000 Uiso R . . . . .
H11 H 0.8174 0.2637 0.0701 0.0342 1.0000 Uiso R . . . . .
H12 H 0.4494 0.3530 0.0377 0.0360 1.0000 Uiso R . . . . .
H13 H -0.1967 1.0295 0.3997 0.0179 1.0000 Uiso R . . . . .
H14 H -0.0493 0.6012 0.4104 0.0183 1.0000 Uiso R . . . . .
H15 H -0.0694 0.6043 0.2862 0.0167 1.0000 Uiso R . . . . .
H16 H -0.2188 1.0471 0.2749 0.0155 1.0000 Uiso R . . . . .
H19 H -0.3080 1.0490 0.1654 0.0174 1.0000 Uiso R . . . . .
H20 H -0.0019 0.6164 0.1760 0.0185 1.0000 Uiso R . . . . .
H21 H -0.0226 0.6304 0.0516 0.0221 1.0000 Uiso R . . . . .
H22 H -0.3187 1.0497 0.0407 0.0204 1.0000 Uiso R . . . . .
H23 H 0.3123 0.6028 0.4797 0.0187 1.0000 Uiso R . . . . .
H24 H 0.3329 0.4419 0.5080 0.0187 1.0000 Uiso R . . . . .
H25 H 0.4570 0.6014 0.5966 0.0500 1.0000 Uiso R . . . . .
S1 S 0.22402(8) 1.23870(5) 0.36690(3) 0.0119 1.0000 Uani . . . . . .
N1 N 0.0561(3) 1.2468(2) 0.42747(10) 0.0221 1.0000 Uani . . . . . .
N2 N 0.3995(3) 0.70341(19) 0.21075(9) 0.0151 1.0000 Uani . . . . . .
N3 N -0.1205(3) 0.8143(2) 0.41714(9) 0.0158 1.0000 Uani . . . . . .
N4 N -0.1725(3) 0.8408(2) 0.03470(9) 0.0178 1.0000 Uani . . . . . .
O1 O 0.2094(3) 1.12730(17) 0.10528(8) 0.0185 1.0000 Uani . . . . . .
O2 O 0.2968(3) 0.88698(18) 0.09195(8) 0.0183 1.0000 Uani . . . . . .
O3 O 0.4193(3) 1.23023(17) 0.40144(9) 0.0185 1.0000 Uani . . . . . .
O4 O 0.1411(3) 1.35579(17) 0.31165(8) 0.0174 1.0000 Uani . . . . . .
O5 O 0.4037(3) 0.4547(2) 0.13201(10) 0.0248 1.0000 Uani . . . . . .
O6 O 0.3697(3) 0.56258(18) 0.58360(8) 0.0169 1.0000 Uani . . . . . .
C1 C 0.2616(3) 1.0761(2) 0.32469(10) 0.0111 1.0000 Uani . . . . . .
C2 C 0.3235(3) 0.9345(2) 0.36068(10) 0.0114 1.0000 Uani . . . . . .
C3 C 0.2446(3) 1.0879(2) 0.25005(10) 0.0121 1.0000 Uani . . . . . .
C4 C 0.2851(3) 0.9660(2) 0.21070(10) 0.0120 1.0000 Uani . . . . . .
C5 C 0.3664(3) 0.8109(2) 0.32404(10) 0.0117 1.0000 Uani . . . . . .
C6 C 0.3506(3) 0.8232(2) 0.24767(10) 0.0117 1.0000 Uani . . . . . .
C7 C 0.2641(3) 0.9886(2) 0.13086(10) 0.0133 1.0000 Uani . . . . . .
C8 C 0.4686(3) 0.5523(2) 0.24233(11) 0.0158 1.0000 Uani . . . . . .
C9 C 0.5467(3) 0.4570(2) 0.18360(12) 0.0171 1.0000 Uani . . . . . .
C10 C 0.7373(4) 0.3782(3) 0.16503(15) 0.0249 1.0000 Uani . . . . . .
C11 C 0.7121(4) 0.3231(3) 0.09726(15) 0.0285 1.0000 Uani . . . . . .
C12 C 0.5105(5) 0.3724(3) 0.08019(14) 0.0300 1.0000 Uani . . . . . .
C13 C -0.1696(3) 0.9420(2) 0.37627(11) 0.0149 1.0000 Uani . . . . . .
C14 C -0.0844(3) 0.6931(2) 0.38238(10) 0.0152 1.0000 Uani . . . . . .
C15 C -0.0952(3) 0.6936(2) 0.30804(10) 0.0139 1.0000 Uani . . . . . .
C16 C -0.1833(3) 0.9537(2) 0.30139(10) 0.0129 1.0000 Uani . . . . . .
C17 C -0.1444(3) 0.8267(2) 0.26563(10) 0.0118 1.0000 Uani . . . . . .
C18 C -0.1532(3) 0.8318(2) 0.18577(10) 0.0116 1.0000 Uani . . . . . .
C19 C -0.2480(3) 0.9613(2) 0.14345(11) 0.0145 1.0000 Uani . . . . . .
C20 C -0.0682(3) 0.7071(2) 0.14954(11) 0.0154 1.0000 Uani . . . . . .
C21 C -0.0812(4) 0.7163(2) 0.07514(11) 0.0184 1.0000 Uani . . . . . .
C22 C -0.2539(4) 0.9607(2) 0.06877(11) 0.0170 1.0000 Uani . . . . . .
C23 C 0.3881(3) 0.5220(2) 0.51128(11) 0.0156 1.0000 Uani . . . . . .
Cl1 Cl 0.35121(8) 0.91036(5) 0.45382(2) 0.0140 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1537(5)

loop_
_oxford_twin_element_scale_factors
0.599(3)
0.150
0.178(5)
0.073(3)
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
H1 . O1 . 0.991 no
H2 . N2 . 0.801 no
H3 . C3 . 0.950 no
H5 . C5 . 0.950 no
H6 . N1 . 1.009 no
H7 . N1 . 0.862 no
H8 . C8 . 0.950 no
H9 . C8 . 0.950 no
H10 . C10 . 0.950 no
H11 . C11 . 0.950 no
H12 . C12 . 0.950 no
H13 . C13 . 0.950 no
H14 . C14 . 0.950 no
H15 . C15 . 0.950 no
H16 . C16 . 0.950 no
H19 . C19 . 0.950 no
H20 . C20 . 0.950 no
H21 . C21 . 0.950 no
H22 . C22 . 0.950 no
H23 . C23 . 0.950 no
H24 . C23 . 0.950 no
H25 . O6 . 0.828 no
S1 . N1 . 1.587(2) yes
S1 . O3 . 1.4472(17) yes
S1 . O4 . 1.4400(16) yes
S1 . C1 . 1.759(2) yes
N2 . C6 . 1.348(3) yes
N2 . C8 . 1.458(3) yes
N3 . C13 . 1.338(3) yes
N3 . C14 . 1.340(3) yes
N4 . C21 . 1.340(3) yes
N4 . C22 . 1.337(3) yes
O1 . C7 . 1.318(3) yes
O2 . C7 . 1.233(2) yes
O5 . C9 . 1.370(3) yes
O5 . C12 . 1.370(3) yes
O6 . C23 . 1.429(3) yes
C1 . C2 . 1.408(3) yes
C1 . C3 . 1.387(3) yes
C2 . C5 . 1.376(3) yes
C2 . Cl1 . 1.7331(18) yes
C3 . C4 . 1.393(3) yes
C4 . C6 . 1.425(3) yes
C4 . C7 . 1.485(3) yes
C5 . C6 . 1.418(3) yes
C8 . C9 . 1.484(3) yes
C9 . C10 . 1.355(3) yes
C10 . C11 . 1.438(4) yes
C11 . C12 . 1.337(4) yes
C13 . C16 . 1.390(3) yes
C14 . C15 . 1.386(3) yes
C15 . C17 . 1.394(3) yes
C16 . C17 . 1.396(3) yes
C17 . C18 . 1.484(3) yes
C18 . C19 . 1.396(3) yes
C18 . C20 . 1.400(3) yes
C19 . C22 . 1.392(3) yes
C20 . C21 . 1.382(3) yes
C23 . C23 2_666 1.517(4) yes
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
N1 . S1 . O3 . 108.30(11) yes
N1 . S1 . O4 . 107.99(10) yes
O3 . S1 . O4 . 118.48(10) yes
N1 . S1 . C1 . 109.74(11) yes
O3 . S1 . C1 . 106.41(10) yes
O4 . S1 . C1 . 105.71(9) yes
H6 . N1 . H7 . 122.5 no
H6 . N1 . S1 . 116.2 no
H7 . N1 . S1 . 118.1 no
H2 . N2 . C6 . 115.5 no
H2 . N2 . C8 . 118.8 no
C6 . N2 . C8 . 125.76(17) yes
C13 . N3 . C14 . 116.65(17) yes
C21 . N4 . C22 . 117.67(18) yes
H1 . O1 . C7 . 107.3 no
C9 . O5 . C12 . 106.4(2) yes
H25 . O6 . C23 . 115.2 no
S1 . C1 . C2 . 124.66(14) yes
S1 . C1 . C3 . 117.51(14) yes
C2 . C1 . C3 . 117.63(17) yes
C1 . C2 . C5 . 122.01(17) yes
C1 . C2 . Cl1 . 120.48(15) yes
C5 . C2 . Cl1 . 117.51(15) yes
H3 . C3 . C1 . 118.8 no
H3 . C3 . C4 . 118.8 no
C1 . C3 . C4 . 122.41(18) yes
C3 . C4 . C6 . 119.44(17) yes
C3 . C4 . C7 . 118.87(17) yes
C6 . C4 . C7 . 121.67(17) yes
H5 . C5 . C2 . 119.9 no
H5 . C5 . C6 . 119.9 no
C2 . C5 . C6 . 120.26(18) yes
C4 . C6 . C5 . 118.24(17) yes
C4 . C6 . N2 . 120.69(17) yes
C5 . C6 . N2 . 121.06(18) yes
C4 . C7 . O1 . 113.87(17) yes
C4 . C7 . O2 . 123.12(18) yes
O1 . C7 . O2 . 123.01(18) yes
N2 . C8 . H8 . 109.8 no
N2 . C8 . H9 . 109.8 no
H8 . C8 . H9 . 109.5 no
N2 . C8 . C9 . 108.17(17) yes
H8 . C8 . C9 . 109.8 no
H9 . C8 . C9 . 109.8 no
C8 . C9 . O5 . 115.94(19) yes
C8 . C9 . C10 . 133.8(2) yes
O5 . C9 . C10 . 109.9(2) yes
H10 . C10 . C9 . 126.8 no
H10 . C10 . C11 . 126.7 no
C9 . C10 . C11 . 106.5(2) yes
C10 . C11 . H11 . 127.0 no
C10 . C11 . C12 . 106.1(2) yes
H11 . C11 . C12 . 126.9 no
H12 . C12 . O5 . 124.5 no
H12 . C12 . C11 . 124.5 no
O5 . C12 . C11 . 111.1(2) yes
H13 . C13 . N3 . 118.2 no
H13 . C13 . C16 . 118.2 no
N3 . C13 . C16 . 123.67(19) yes
H14 . C14 . N3 . 118.0 no
H14 . C14 . C15 . 118.0 no
N3 . C14 . C15 . 123.91(19) yes
H15 . C15 . C14 . 120.4 no
H15 . C15 . C17 . 120.4 no
C14 . C15 . C17 . 119.26(19) yes
H16 . C16 . C13 . 120.4 no
H16 . C16 . C17 . 120.4 no
C13 . C16 . C17 . 119.27(19) yes
C16 . C17 . C15 . 117.24(18) yes
C16 . C17 . C18 . 121.85(18) yes
C15 . C17 . C18 . 120.91(18) yes
C17 . C18 . C19 . 121.40(18) yes
C17 . C18 . C20 . 121.59(17) yes
C19 . C18 . C20 . 117.01(17) yes
H19 . C19 . C18 . 120.3 no
H19 . C19 . C22 . 120.3 no
C18 . C19 . C22 . 119.41(19) yes
H20 . C20 . C18 . 120.1 no
H20 . C20 . C21 . 120.1 no
C18 . C20 . C21 . 119.74(19) yes
H21 . C21 . C20 . 118.4 no
H21 . C21 . N4 . 118.5 no
C20 . C21 . N4 . 123.1(2) yes
H22 . C22 . C19 . 118.4 no
H22 . C22 . N4 . 118.5 no
C19 . C22 . N4 . 123.10(19) yes
C23 2_666 C23 . O6 . 111.4(2) yes
C23 2_666 C23 . H23 . 109.0 no
O6 . C23 . H23 . 109.0 no
C23 2_666 C23 . H24 . 109.0 no
O6 . C23 . H24 . 109.0 no
H23 . C23 . H24 . 109.5 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
O1 . H1 . N4 2_575 150.90 0.991 1.691 2.602(3) yes
O1 . H1 . C22 2_575 151.87 0.991 2.503 3.410(3) yes
N2 . H2 . O2 . 139.82 0.801 2.002 2.664(3) yes
N1 . H6 . N3 2_576 152.71 1.009 1.977 2.910(3) yes
N1 . H7 . O6 2_576 166.21 0.862 2.086 2.931(3) yes
C8 . H9 . O4 1_545 157.01 0.950 2.571 3.465(3) yes
C15 . H15 . O4 1_545 137.08 0.950 2.405 3.168(3) yes
C22 . H22 . O2 2_575 128.93 0.950 2.505 3.188(3) yes
O6 . H25 . O3 2_676 153.47 0.828 2.018 2.783(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/06/12 at 13:04:30
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE N   (   1,X'S) H   (   6,X'S) H   (   7,X'S) 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE O   (   6,X'S) H   (  25,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   8,X'S) H   (   8,X'S) H   (   9,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
RIDE C   (  21,X'S) H   (  21,X'S) 
RIDE C   (  22,X'S) H   (  22,X'S) 
RIDE C   (  23,X'S) H   (  23,X'S) H   (  24,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/06/12 at 13:04:30
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# 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 3 x .
0 0 4 x .
0 7 1 x .
0 -3 13 x .
0 3 2 x .
0 4 3 x .
0 4 4 x .
0 -1 3 x .
_database_code_depnum_ccdc_archive 'CCDC 943032'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_FUS-BP-HYD
_audit_creation_date             12-06-08
_audit_creation_method           CRYSTALS_ver_14.23

_oxford_structure_analysis_title 'x84313_0m in P-1'
_chemical_name_systematic        'Furosemide - bipyridyl-hydroquinone'
_chemical_melting_point          ?

# Hand-made tables can be put in the cif. The number of columns 
# is set in the loop header. 
# The contants of each column can either be a piece of text 
# without any spaces (eg a number) or other text enclosed in " " 
# Remove the leading # in the following example 

#geom_extra_table_head_A 
#; 
#Table 2. 
#Molecular parameters deviating most from MOGUL averages 
#; 
# 
#loop_ 
#_geom_extra_tableA_col_1 
#_geom_extra_tableA_col_2 
#_geom_extra_tableA_col_3 
#_geom_extra_tableA_col_4 
# 
#Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" 
#N5-C6-C4 129 124 "7 (\%)" 
#C3-O10-C2 105 109 "2 (\%)" 
#C6-O7 1.25 1.22 ".02 (\%A)" 
# 


_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                   6.9302(4)
_cell_length_b                   9.9356(6)
_cell_length_c                   18.6298(11)
_cell_angle_alpha                83.633(3)
_cell_angle_beta                 89.624(3)
_cell_angle_gamma                72.794(3)
_cell_volume                     1217.34(13)

_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 0.0033 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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C25 H21 Cl1 N4 O6 S1 
# Dc =      0.74 Fooo =    562.00 Mu =      1.47 M =    270.49
# Found Formula = C50 H44 Cl2 N8 O12 S2 
# Dc =      1.48 FOOO =    562.00 Mu =      2.93 M =    541.99

_chemical_formula_sum            'C25 H22 Cl N4 O6 S'
_chemical_formula_moiety         'C12 H11 Cl N2 O5 S, C10 H8 N2, 0.5(C6 H6 O2)'
_chemical_compound_source        ?
_chemical_formula_weight         541.98


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_max          0.120

_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             562
_exptl_absorpt_coefficient_mu    0.293

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9854
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      100
_diffrn_reflns_number            21940
_reflns_number_total             6308
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6308 
# Theoretical number of reflections is about 12852 


_diffrn_reflns_theta_min         1.100
_diffrn_reflns_theta_max         28.922
_diffrn_measured_fraction_theta_max 0.981

_diffrn_reflns_theta_full        25.162
_diffrn_measured_fraction_theta_full 0.993


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.43


# 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>2.0\s(I)
_refine_ls_number_reflns         5405
_refine_ls_number_restraints     0
_refine_ls_number_parameters     334
_oxford_refine_ls_R_factor_ref   0.0436
_refine_ls_wR_factor_ref         0.0366
_refine_ls_goodness_of_fit_ref   1.0981
_refine_ls_shift/su_max          0.0009833
_refine_ls_shift/su_mean         0.0000484


# The values computed from all data 
_oxford_reflns_number_all        6292
_refine_ls_R_factor_all          0.0543
_refine_ls_wR_factor_all         0.0477

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5405
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_gt          0.0366

# 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 # none, 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: 
 0.263 0.296 0.132 
;

# 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
H1 H 0.8385 0.3565 0.9996 0.0500 1.0000 Uiso R . . . . .
H2 H 0.6269 0.7510 0.8857 0.0500 1.0000 Uiso R . . . . .
H3 H 0.8597 0.2966 0.8373 0.0148 1.0000 Uiso R . . . . .
H5 H 0.6517 0.7478 0.7062 0.0149 1.0000 Uiso R . . . . .
H6 H 0.7496 0.2837 0.5927 0.0500 1.0000 Uiso R . . . . .
H7 H 0.6611 0.1987 0.6462 0.0500 1.0000 Uiso R . . . . .
H8 H 0.6604 0.9260 0.7788 0.0194 1.0000 Uiso R . . . . .
H9 H 0.4438 0.9119 0.7745 0.0194 1.0000 Uiso R . . . . .
H10 H 0.1750 1.0844 0.8598 0.0261 1.0000 Uiso R . . . . .
H11 H 0.2323 1.2343 0.9567 0.0271 1.0000 Uiso R . . . . .
H12 H 0.5981 1.1811 0.9738 0.0274 1.0000 Uiso R . . . . .
H13 H 0.2898 0.4554 0.5439 0.0240 1.0000 Uiso R . . . . .
H14 H 0.2058 0.8660 0.5225 0.0230 1.0000 Uiso R . . . . .
H15 H 0.1793 0.8730 0.6461 0.0203 1.0000 Uiso R . . . . .
H16 H 0.2610 0.4489 0.6679 0.0199 1.0000 Uiso R . . . . .
H19 H 0.3363 0.4488 0.7795 0.0173 1.0000 Uiso R . . . . .
H20 H 0.0478 0.8716 0.7526 0.0185 1.0000 Uiso R . . . . .
H21 H 0.0225 0.8641 0.8769 0.0200 1.0000 Uiso R . . . . .
H22 H 0.3079 0.4555 0.9034 0.0191 1.0000 Uiso R . . . . .
H23 H 1.2571 0.1133 0.4090 0.0181 1.0000 Uiso R . . . . .
H24 H 1.2144 0.1821 0.5256 0.0184 1.0000 Uiso R . . . . .
H25 H 1.3402 0.1268 0.6435 0.0500 1.0000 Uiso R . . . . .
O6 O 1.45802(17) 0.07522(12) 0.63932(6) 0.0178 1.0000 Uani . . . . . .
C23 C 1.3560(2) 0.06733(16) 0.44598(8) 0.0150 1.0000 Uani . . . . . .
C24 C 1.3302(2) 0.10809(16) 0.51525(8) 0.0153 1.0000 Uani . . . . . .
C25 C 1.4748(2) 0.03990(15) 0.56946(8) 0.0139 1.0000 Uani . . . . . .
S1 S 0.90945(6) 0.24503(4) 0.692772(19) 0.0134 1.0000 Uani . . . . . .
N1 N 0.7522(2) 0.23840(15) 0.63265(7) 0.0213 1.0000 Uani . . . . . .
N2 N 0.6257(2) 0.76286(13) 0.84367(6) 0.0147 1.0000 Uani . . . . . .
N3 N 0.2486(2) 0.66113(15) 0.52080(7) 0.0186 1.0000 Uani . . . . . .
N4 N 0.1647(2) 0.65979(14) 0.90145(7) 0.0156 1.0000 Uani . . . . . .
O1 O 0.83874(17) 0.35492(11) 0.95768(5) 0.0164 1.0000 Uani . . . . . .
O2 O 0.6990(2) 0.58677(12) 0.96471(6) 0.0219 1.0000 Uani . . . . . .
O3 O 1.08839(17) 0.25795(12) 0.65571(6) 0.0200 1.0000 Uani . . . . . .
O4 O 0.92922(19) 0.12743(11) 0.74723(6) 0.0194 1.0000 Uani . . . . . .
O5 O 0.63298(18) 1.04283(12) 0.89635(6) 0.0208 1.0000 Uani . . . . . .
C1 C 0.8168(2) 0.40060(15) 0.73545(8) 0.0122 1.0000 Uani . . . . . .
C2 C 0.7558(2) 0.53718(15) 0.69798(7) 0.0115 1.0000 Uani . . . . . .
C3 C 0.8174(2) 0.38834(15) 0.81097(7) 0.0123 1.0000 Uani . . . . . .
C4 C 0.7578(2) 0.50681(15) 0.84860(7) 0.0118 1.0000 Uani . . . . . .
C5 C 0.6935(2) 0.65677(15) 0.73328(7) 0.0124 1.0000 Uani . . . . . .
C6 C 0.6912(2) 0.64507(15) 0.80977(7) 0.0120 1.0000 Uani . . . . . .
C7 C 0.7617(2) 0.48720(15) 0.92875(8) 0.0135 1.0000 Uani . . . . . .
C8 C 0.5538(2) 0.90601(15) 0.80606(8) 0.0161 1.0000 Uani . . . . . .
C9 C 0.4861(2) 1.01176(16) 0.85817(8) 0.0164 1.0000 Uani . . . . . .
C10 C 0.3015(3) 1.08669(17) 0.87805(9) 0.0218 1.0000 Uani . . . . . .
C11 C 0.3333(3) 1.17030(17) 0.93209(9) 0.0225 1.0000 Uani . . . . . .
C12 C 0.5336(3) 1.14034(17) 0.94097(9) 0.0229 1.0000 Uani . . . . . .
C13 C 0.2654(3) 0.54160(18) 0.56489(8) 0.0200 1.0000 Uani . . . . . .
C14 C 0.2173(3) 0.78001(17) 0.55252(8) 0.0191 1.0000 Uani . . . . . .
C15 C 0.2006(2) 0.78553(16) 0.62656(8) 0.0169 1.0000 Uani . . . . . .
C16 C 0.2492(2) 0.53649(16) 0.63931(8) 0.0166 1.0000 Uani . . . . . .
C17 C 0.2154(2) 0.66092(15) 0.67200(7) 0.0121 1.0000 Uani . . . . . .
C18 C 0.1960(2) 0.66031(15) 0.75143(7) 0.0119 1.0000 Uani . . . . . .
C19 C 0.2725(2) 0.53584(16) 0.79811(8) 0.0144 1.0000 Uani . . . . . .
C20 C 0.1020(2) 0.78444(16) 0.78234(8) 0.0154 1.0000 Uani . . . . . .
C21 C 0.0886(2) 0.77923(16) 0.85666(8) 0.0166 1.0000 Uani . . . . . .
C22 C 0.2542(2) 0.54078(16) 0.87214(8) 0.0160 1.0000 Uani . . . . . .
Cl1 Cl 0.75328(6) 0.56237(4) 0.604483(18) 0.0151 1.0000 Uani . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.11443(13)
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
H1 . O1 . 0.783 no
H2 . N2 . 0.778 no
H3 . C3 . 0.950 no
H5 . C5 . 0.950 no
H6 . N1 . 0.824 no
H7 . N1 . 0.860 no
H8 . C8 . 0.950 no
H9 . C8 . 0.950 no
H10 . C10 . 0.950 no
H11 . C11 . 0.950 no
H12 . C12 . 0.950 no
H13 . C13 . 0.950 no
H14 . C14 . 0.950 no
H15 . C15 . 0.950 no
H16 . C16 . 0.950 no
H19 . C19 . 0.950 no
H20 . C20 . 0.950 no
H21 . C21 . 0.950 no
H22 . C22 . 0.950 no
H23 . C23 . 0.950 no
H24 . C24 . 0.950 no
H25 . O6 . 0.834 no
O6 . C25 . 1.3806(17) yes
C23 . C25 2_856 1.385(2) yes
C23 . C24 . 1.390(2) yes
C24 . C25 . 1.394(2) yes
S1 . N1 . 1.5880(14) yes
S1 . O3 . 1.4472(12) yes
S1 . O4 . 1.4344(11) yes
S1 . C1 . 1.7642(14) yes
N2 . C6 . 1.3493(18) yes
N2 . C8 . 1.4582(19) yes
N3 . C13 . 1.342(2) yes
N3 . C14 . 1.339(2) yes
N4 . C21 . 1.3412(19) yes
N4 . C22 . 1.336(2) yes
O1 . C7 . 1.3169(18) yes
O2 . C7 . 1.2269(18) yes
O5 . C9 . 1.3717(19) yes
O5 . C12 . 1.3713(19) yes
C1 . C2 . 1.4006(19) yes
C1 . C3 . 1.3986(19) yes
C2 . C5 . 1.3773(19) yes
C2 . Cl1 . 1.7315(14) yes
C3 . C4 . 1.3926(19) yes
C4 . C6 . 1.4255(19) yes
C4 . C7 . 1.4836(19) yes
C5 . C6 . 1.4171(19) yes
C8 . C9 . 1.482(2) yes
C9 . C10 . 1.349(2) yes
C10 . C11 . 1.431(2) yes
C11 . C12 . 1.338(3) yes
C13 . C16 . 1.387(2) yes
C14 . C15 . 1.389(2) yes
C15 . C17 . 1.398(2) yes
C16 . C17 . 1.396(2) yes
C17 . C18 . 1.4845(19) yes
C18 . C19 . 1.395(2) yes
C18 . C20 . 1.398(2) yes
C19 . C22 . 1.389(2) yes
C20 . C21 . 1.383(2) yes
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
H25 . O6 . C25 . 107.4 no
H23 . C23 . C25 2_856 119.8 no
H23 . C23 . C24 . 119.9 no
C25 2_856 C23 . C24 . 120.29(14) yes
H24 . C24 . C23 . 120.1 no
H24 . C24 . C25 . 120.1 no
C23 . C24 . C25 . 119.75(14) yes
C24 . C25 . C23 2_856 119.96(13) yes
C24 . C25 . O6 . 122.60(14) yes
C23 2_856 C25 . O6 . 117.43(13) yes
N1 . S1 . O3 . 106.89(7) yes
N1 . S1 . O4 . 108.04(7) yes
O3 . S1 . O4 . 118.56(7) yes
N1 . S1 . C1 . 110.41(7) yes
O3 . S1 . C1 . 105.96(7) yes
O4 . S1 . C1 . 106.90(7) yes
H7 . N1 . H6 . 123.2 no
H7 . N1 . S1 . 117.0 no
H6 . N1 . S1 . 119.0 no
H2 . N2 . C6 . 116.1 no
H2 . N2 . C8 . 120.1 no
C6 . N2 . C8 . 123.75(12) yes
C13 . N3 . C14 . 116.31(13) yes
C21 . N4 . C22 . 117.82(13) yes
H1 . O1 . C7 . 106.5 no
C9 . O5 . C12 . 106.21(13) yes
S1 . C1 . C2 . 123.49(11) yes
S1 . C1 . C3 . 118.50(11) yes
C2 . C1 . C3 . 117.85(13) yes
C1 . C2 . C5 . 121.95(12) yes
C1 . C2 . Cl1 . 120.97(11) yes
C5 . C2 . Cl1 . 117.07(11) yes
H3 . C3 . C1 . 119.1 no
H3 . C3 . C4 . 119.1 no
C1 . C3 . C4 . 121.86(13) yes
C3 . C4 . C6 . 119.71(13) yes
C3 . C4 . C7 . 119.43(13) yes
C6 . C4 . C7 . 120.84(12) yes
H5 . C5 . C2 . 119.8 no
H5 . C5 . C6 . 119.7 no
C2 . C5 . C6 . 120.49(13) yes
C4 . C6 . C5 . 118.10(13) yes
C4 . C6 . N2 . 121.97(12) yes
C5 . C6 . N2 . 119.92(13) yes
C4 . C7 . O1 . 114.50(12) yes
C4 . C7 . O2 . 122.35(13) yes
O1 . C7 . O2 . 123.16(13) yes
N2 . C8 . H8 . 109.2 no
N2 . C8 . H9 . 109.1 no
H8 . C8 . H9 . 109.5 no
N2 . C8 . C9 . 110.77(12) yes
H8 . C8 . C9 . 109.1 no
H9 . C8 . C9 . 109.1 no
C8 . C9 . O5 . 117.26(14) yes
C8 . C9 . C10 . 132.71(15) yes
O5 . C9 . C10 . 110.02(13) yes
H10 . C10 . C9 . 126.7 no
H10 . C10 . C11 . 126.7 no
C9 . C10 . C11 . 106.64(15) yes
C10 . C11 . H11 . 126.8 no
C10 . C11 . C12 . 106.33(15) yes
H11 . C11 . C12 . 126.8 no
H12 . C12 . O5 . 124.6 no
H12 . C12 . C11 . 124.6 no
O5 . C12 . C11 . 110.80(14) yes
H13 . C13 . N3 . 118.1 no
H13 . C13 . C16 . 118.1 no
N3 . C13 . C16 . 123.86(15) yes
H14 . C14 . N3 . 117.9 no
H14 . C14 . C15 . 117.9 no
N3 . C14 . C15 . 124.10(14) yes
H15 . C15 . C14 . 120.4 no
H15 . C15 . C17 . 120.4 no
C14 . C15 . C17 . 119.22(14) yes
H16 . C16 . C13 . 120.2 no
H16 . C16 . C17 . 120.2 no
C13 . C16 . C17 . 119.54(14) yes
C15 . C17 . C16 . 116.97(13) yes
C15 . C17 . C18 . 121.75(13) yes
C16 . C17 . C18 . 121.29(13) yes
C17 . C18 . C19 . 121.18(13) yes
C17 . C18 . C20 . 121.35(13) yes
C19 . C18 . C20 . 117.47(13) yes
H19 . C19 . C18 . 120.4 no
H19 . C19 . C22 . 120.4 no
C18 . C19 . C22 . 119.20(14) yes
H20 . C20 . C18 . 120.3 no
H20 . C20 . C21 . 120.3 no
C18 . C20 . C21 . 119.42(14) yes
H21 . C21 . C20 . 118.5 no
H21 . C21 . N4 . 118.5 no
C20 . C21 . N4 . 122.96(14) yes
H22 . C22 . C19 . 118.4 no
H22 . C22 . N4 . 118.5 no
C19 . C22 . N4 . 123.11(14) yes
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
O1 . H1 . N4 2_667 173.59 0.783 1.833 2.613(2) yes
N2 . H2 . O2 . 138.13 0.778 2.018 2.649(2) yes
N1 . H6 . N3 2_666 162.40 0.824 2.125 2.921(2) yes
N1 . H7 . O6 1_455 157.88 0.860 2.136 2.951(2) yes
C11 . H11 . O2 2_677 124.37 0.950 2.572 3.206(2) yes
C16 . H16 . O3 1_455 131.27 0.950 2.554 3.260(2) yes
C20 . H20 . O4 1_465 146.17 0.950 2.420 3.252(2) yes
C22 . H22 . O2 2_667 129.60 0.950 2.449 3.141(2) yes
O6 . H25 . O3 . 173.60 0.834 1.873 2.704(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/06/12 at 13:05:19
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE O   (   6,X'S) H   (  25,X'S) 
RIDE C   (  23,X'S) H   (  23,X'S) 
RIDE C   (  24,X'S) H   (  24,X'S) 
RIDE N   (   1,X'S) H   (   7,X'S) H   (   6,X'S) 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE O   (   1,X'S) H   (   1,X'S) 
RIDE C   (   3,X'S) H   (   3,X'S) 
RIDE C   (   5,X'S) H   (   5,X'S) 
RIDE C   (   8,X'S) H   (   8,X'S) H   (   9,X'S) 
RIDE C   (  10,X'S) H   (  10,X'S) 
RIDE C   (  11,X'S) H   (  11,X'S) 
RIDE C   (  12,X'S) H   (  12,X'S) 
RIDE C   (  13,X'S) H   (  13,X'S) 
RIDE C   (  14,X'S) H   (  14,X'S) 
RIDE C   (  15,X'S) H   (  15,X'S) 
RIDE C   (  16,X'S) H   (  16,X'S) 
RIDE C   (  19,X'S) H   (  19,X'S) 
RIDE C   (  20,X'S) H   (  20,X'S) 
RIDE C   (  21,X'S) H   (  21,X'S) 
RIDE C   (  22,X'S) H   (  22,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/06/12 at 13:05:19
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 943033'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_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                   7.3972(7)
_cell_length_b                   9.3373(8)
_cell_length_c                   18.1141(16)
_cell_angle_alpha                80.504(4)
_cell_angle_beta                 82.039(4)
_cell_angle_gamma                75.173(4)
_cell_volume                     1186.81(19)

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
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 0.0033 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'
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 0.1246 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'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C20 H24 Cl1 N4 O6 S1 
# Dc =      1.35 Fooo =    554.00 Mu =      2.91 M =    483.95
# Found Formula = C24 H24 Cl1 N4 O6 S1 
# Dc =      1.49 FOOO =    554.00 Mu =      2.99 M =    532.00

_chemical_formula_sum            'C24 H24 Cl1 N4 O6 S1'
_chemical_formula_moiety         'C24 H24 Cl1 N4 O6 S1'
_chemical_compound_source        ?
_chemical_formula_weight         532.00


_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             554
_exptl_absorpt_coefficient_mu    0.299

# Sheldrick geometric approximatio 0.96 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_T_max  0.9705
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_device       Serial
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_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      100
_diffrn_reflns_number            41318
_reflns_number_total             11284
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11284 
# Theoretical number of reflections is about 23423 


_diffrn_reflns_theta_min         1.146
_diffrn_reflns_theta_max         36.572
_diffrn_measured_fraction_theta_max 0.962

_diffrn_reflns_theta_full        25.601
_diffrn_measured_fraction_theta_full 0.988


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              -15
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.56


# 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         7624
_refine_ls_number_restraints     0
_refine_ls_number_parameters     325
_oxford_refine_ls_R_factor_ref   0.0376
_refine_ls_wR_factor_ref         0.0423
_refine_ls_goodness_of_fit_ref   1.0302
_refine_ls_shift/su_max          0.0015313
_refine_ls_shift/su_mean         0.0000640


# The values computed from all data 
_oxford_reflns_number_all        11266
_refine_ls_R_factor_all          0.0600
_refine_ls_wR_factor_all         0.0684

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                9213
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_gt          0.0482

# 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 # none, 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: 
 0.185 0.162 0.544E-01 
;

# 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
Cl1 Cl 0.66664(4) 0.90882(3) 0.651019(13) 0.0147 1.0000 Uani . . . . . .
C2 C 0.55890(15) 0.93284(12) 0.74098(5) 0.0111 1.0000 Uani . . . . . .
C3 C 0.53534(15) 0.80600(12) 0.78866(6) 0.0123 1.0000 Uani . . . . . .
C4 C 0.45112(15) 0.81528(12) 0.86345(6) 0.0114 1.0000 Uani . . . . . .
N5 N 0.42337(14) 0.69152(11) 0.90942(5) 0.0142 1.0000 Uani . . . . . .
C6 C 0.46726(17) 0.54222(13) 0.88732(6) 0.0157 1.0000 Uani . . . . . .
C7 C 0.67281(17) 0.47005(12) 0.87919(6) 0.0151 1.0000 Uani . . . . . .
O8 O 0.76531(13) 0.44293(10) 0.94276(5) 0.0189 1.0000 Uani . . . . . .
C9 C 0.94913(19) 0.37445(15) 0.92214(8) 0.0231 1.0000 Uani . . . . . .
C10 C 0.97415(19) 0.35991(14) 0.84814(8) 0.0223 1.0000 Uani . . . . . .
C11 C 0.79427(18) 0.42141(14) 0.82027(7) 0.0191 1.0000 Uani . . . . . .
C12 C 0.39843(15) 0.95906(12) 0.88826(5) 0.0113 1.0000 Uani . . . . . .
C13 C 0.42498(15) 1.08471(12) 0.83840(5) 0.0116 1.0000 Uani . . . . . .
C14 C 0.50046(15) 1.07559(12) 0.76385(5) 0.0112 1.0000 Uani . . . . . .
S15 S 0.52309(4) 1.24165(3) 0.704063(14) 0.0119 1.0000 Uani . . . . . .
O16 O 0.42573(14) 1.36250(10) 0.74589(5) 0.0175 1.0000 Uani . . . . . .
O17 O 0.72050(13) 1.22758(10) 0.67883(5) 0.0178 1.0000 Uani . . . . . .
N18 N 0.41947(15) 1.25844(12) 0.63040(5) 0.0159 1.0000 Uani . . . . . .
C19 C 0.31086(15) 0.97751(12) 0.96625(6) 0.0129 1.0000 Uani . . . . . .
O20 O 0.28492(13) 1.11323(9) 0.98383(4) 0.0160 1.0000 Uani . . . . . .
O21 O 0.26550(14) 0.87510(10) 1.01034(5) 0.0197 1.0000 Uani . . . . . .
O22 O 0.01668(14) 1.36204(12) 0.63941(6) 0.0227 1.0000 Uani . . . . . .
C23 C -0.0594(2) 1.51284(15) 0.60723(8) 0.0221 1.0000 Uani . . . . . .
C24 C -0.09099(19) 1.52461(16) 0.52503(8) 0.0230 1.0000 Uani . . . . . .
N25 N -0.09678(14) 0.86708(11) 0.88291(5) 0.0139 1.0000 Uani . . . . . .
C26 C -0.04249(18) 0.73708(13) 0.85447(6) 0.0160 1.0000 Uani . . . . . .
C27 C 0.05167(17) 0.72323(13) 0.78309(6) 0.0147 1.0000 Uani . . . . . .
C28 C 0.09151(15) 0.85024(12) 0.73822(5) 0.0112 1.0000 Uani . . . . . .
C29 C 0.18806(15) 0.84217(12) 0.66120(6) 0.0122 1.0000 Uani . . . . . .
C30 C 0.31122(16) 0.71074(13) 0.64069(6) 0.0143 1.0000 Uani . . . . . .
C31 C 0.39760(17) 0.70994(14) 0.56743(6) 0.0171 1.0000 Uani . . . . . .
N32 N 0.37337(17) 0.82927(14) 0.51441(6) 0.0216 1.0000 Uani . . . . . .
C33 C 0.2550(2) 0.95505(16) 0.53449(7) 0.0251 1.0000 Uani . . . . . .
C34 C 0.15870(19) 0.96655(14) 0.60557(6) 0.0198 1.0000 Uani . . . . . .
C35 C 0.03632(16) 0.98511(12) 0.76844(6) 0.0134 1.0000 Uani . . . . . .
C36 C -0.05683(17) 0.98889(13) 0.84052(6) 0.0146 1.0000 Uani . . . . . .
H31 H 0.5757 0.7132 0.7702 0.0151 1.0000 Uiso R . . . . .
H62 H 0.4052 0.4797 0.9266 0.0199 1.0000 Uiso R . . . . .
H61 H 0.4171 0.5457 0.8390 0.0204 1.0000 Uiso R . . . . .
H91 H 1.0357 0.3453 0.9580 0.0286 1.0000 Uiso R . . . . .
H101 H 1.0886 0.3166 0.8212 0.0286 1.0000 Uiso R . . . . .
H111 H 0.7641 0.4274 0.7704 0.0244 1.0000 Uiso R . . . . .
H131 H 0.3925 1.1779 0.8561 0.0134 1.0000 Uiso R . . . . .
H232 H 0.0297 1.5728 0.6117 0.0273 1.0000 Uiso R . . . . .
H231 H -0.1796 1.5515 0.6360 0.0268 1.0000 Uiso R . . . . .
H241 H -0.1486 1.6287 0.5070 0.0292 1.0000 Uiso R . . . . .
H242 H -0.1777 1.4614 0.5205 0.0291 1.0000 Uiso R . . . . .
H261 H -0.0713 0.6522 0.8846 0.0206 1.0000 Uiso R . . . . .
H271 H 0.0868 0.6293 0.7653 0.0180 1.0000 Uiso R . . . . .
H301 H 0.3376 0.6238 0.6750 0.0182 1.0000 Uiso R . . . . .
H311 H 0.4791 0.6204 0.5538 0.0215 1.0000 Uiso R . . . . .
H331 H 0.2348 1.0394 0.4967 0.0316 1.0000 Uiso R . . . . .
H341 H 0.0746 1.0569 0.6156 0.0242 1.0000 Uiso R . . . . .
H351 H 0.0626 1.0739 0.7418 0.0172 1.0000 Uiso R . . . . .
H361 H -0.0939 1.0794 0.8612 0.0178 1.0000 Uiso R . . . . .
H1 H 0.3689 0.7049 0.9529 0.0500 1.0000 Uiso R . . . . .
H2 H 0.2973 1.2804 0.6342 0.0500 1.0000 Uiso R . . . . .
H3 H -0.0780 1.3218 0.6497 0.0500 1.0000 Uiso R . . . . .
H4 H 0.4848 1.2094 0.5927 0.0500 1.0000 Uiso R . . . . .
H5 H 0.2355 1.1097 1.0275 0.0500 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.13854(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
Cl1 . C2 . 1.7350(10) yes
C2 . C3 . 1.3804(15) yes
C2 . C14 . 1.4046(15) yes
C3 . C4 . 1.4172(14) yes
C3 . H31 . 0.942 no
C4 . N5 . 1.3518(14) yes
C4 . C12 . 1.4279(15) yes
N5 . C6 . 1.4578(15) yes
N5 . H1 . 0.847 no
C6 . C7 . 1.4947(17) yes
C6 . H62 . 0.983 no
C6 . H61 . 0.989 no
C7 . O8 . 1.3753(15) yes
C7 . C11 . 1.3558(16) yes
O8 . C9 . 1.3750(16) yes
C9 . C10 . 1.352(2) yes
C9 . H91 . 0.934 no
C10 . C11 . 1.433(2) yes
C10 . H101 . 0.946 no
C11 . H111 . 0.950 no
C12 . C13 . 1.3965(15) yes
C12 . C19 . 1.4881(14) yes
C13 . C14 . 1.3955(14) yes
C13 . H131 . 0.939 no
C14 . S15 . 1.7702(11) yes
S15 . O16 . 1.4426(9) yes
S15 . O17 . 1.4475(9) yes
S15 . N18 . 1.5954(10) yes
N18 . H2 . 0.870 no
N18 . H4 . 0.899 no
C19 . O20 . 1.3175(14) yes
C19 . O21 . 1.2260(14) yes
O20 . H5 . 0.824 no
O22 . C23 . 1.4331(17) yes
O22 . H3 . 0.861 no
C23 . C24 . 1.521(2) yes
C23 . H232 . 0.986 no
C23 . H231 . 0.982 no
C24 . C24 2_586 1.526(3) yes
C24 . H241 . 0.977 no
C24 . H242 . 0.996 no
N25 . C26 . 1.3415(15) yes
N25 . C36 . 1.3385(15) yes
C26 . C27 . 1.3905(15) yes
C26 . H261 . 0.940 no
C27 . C28 . 1.3958(15) yes
C27 . H271 . 0.945 no
C28 . C29 . 1.4809(14) yes
C28 . C35 . 1.3981(15) yes
C29 . C30 . 1.3995(15) yes
C29 . C34 . 1.3989(16) yes
C30 . C31 . 1.3911(15) yes
C30 . H301 . 0.933 no
C31 . N32 . 1.3373(17) yes
C31 . H311 . 0.944 no
N32 . C33 . 1.3433(18) yes
C33 . C34 . 1.3890(16) yes
C33 . H331 . 0.950 no
C34 . H341 . 0.939 no
C35 . C36 . 1.3908(15) yes
C35 . H351 . 0.939 no
C36 . H361 . 0.942 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
Cl1 . C2 . C3 . 117.10(8) yes
Cl1 . C2 . C14 . 120.93(8) yes
C3 . C2 . C14 . 121.97(9) yes
C2 . C3 . C4 . 120.79(10) yes
C2 . C3 . H31 . 118.4 no
C4 . C3 . H31 . 120.8 no
C3 . C4 . N5 . 120.72(10) yes
C3 . C4 . C12 . 117.68(9) yes
N5 . C4 . C12 . 121.60(9) yes
C4 . N5 . C6 . 124.70(9) yes
C4 . N5 . H1 . 116.1 no
C6 . N5 . H1 . 119.0 no
N5 . C6 . C7 . 113.85(10) yes
N5 . C6 . H62 . 107.4 no
C7 . C6 . H62 . 108.4 no
N5 . C6 . H61 . 110.3 no
C7 . C6 . H61 . 108.2 no
H62 . C6 . H61 . 108.7 no
C6 . C7 . O8 . 116.94(9) yes
C6 . C7 . C11 . 133.09(11) yes
O8 . C7 . C11 . 109.96(11) yes
C7 . O8 . C9 . 106.52(10) yes
O8 . C9 . C10 . 110.45(12) yes
O8 . C9 . H91 . 119.9 no
C10 . C9 . H91 . 129.7 no
C9 . C10 . C11 . 106.31(11) yes
C9 . C10 . H101 . 125.9 no
C11 . C10 . H101 . 127.8 no
C10 . C11 . C7 . 106.75(11) yes
C10 . C11 . H111 . 127.3 no
C7 . C11 . H111 . 125.9 no
C4 . C12 . C13 . 119.80(9) yes
C4 . C12 . C19 . 120.80(9) yes
C13 . C12 . C19 . 119.38(9) yes
C12 . C13 . C14 . 122.17(10) yes
C12 . C13 . H131 . 118.6 no
C14 . C13 . H131 . 119.2 no
C2 . C14 . C13 . 117.48(9) yes
C2 . C14 . S15 . 123.53(8) yes
C13 . C14 . S15 . 118.97(8) yes
C14 . S15 . O16 . 105.65(5) yes
C14 . S15 . O17 . 107.88(5) yes
O16 . S15 . O17 . 118.70(6) yes
C14 . S15 . N18 . 110.24(5) yes
O16 . S15 . N18 . 107.93(6) yes
O17 . S15 . N18 . 106.35(5) yes
S15 . N18 . H2 . 119.0 no
S15 . N18 . H4 . 116.7 no
H2 . N18 . H4 . 119.5 no
C12 . C19 . O20 . 114.47(9) yes
C12 . C19 . O21 . 122.76(10) yes
O20 . C19 . O21 . 122.77(9) yes
C19 . O20 . H5 . 105.5 no
C23 . O22 . H3 . 105.0 no
O22 . C23 . C24 . 112.46(11) yes
O22 . C23 . H232 . 107.8 no
C24 . C23 . H232 . 109.5 no
O22 . C23 . H231 . 108.6 no
C24 . C23 . H231 . 109.1 no
H232 . C23 . H231 . 109.2 no
C24 2_586 C24 . C23 . 112.78(15) yes
C24 2_586 C24 . H241 . 108.3 no
C23 . C24 . H241 . 108.7 no
C24 2_586 C24 . H242 . 108.7 no
C23 . C24 . H242 . 109.4 no
H241 . C24 . H242 . 108.9 no
C26 . N25 . C36 . 118.18(9) yes
N25 . C26 . C27 . 123.20(11) yes
N25 . C26 . H261 . 117.5 no
C27 . C26 . H261 . 119.3 no
C26 . C27 . C28 . 118.89(10) yes
C26 . C27 . H271 . 120.2 no
C28 . C27 . H271 . 120.9 no
C27 . C28 . C29 . 121.04(9) yes
C27 . C28 . C35 . 117.66(9) yes
C29 . C28 . C35 . 121.30(10) yes
C28 . C29 . C30 . 121.86(10) yes
C28 . C29 . C34 . 121.01(10) yes
C30 . C29 . C34 . 117.13(9) yes
C29 . C30 . C31 . 119.23(11) yes
C29 . C30 . H301 . 121.7 no
C31 . C30 . H301 . 119.1 no
C30 . C31 . N32 . 123.96(11) yes
C30 . C31 . H311 . 118.7 no
N32 . C31 . H311 . 117.3 no
C31 . N32 . C33 . 116.48(10) yes
N32 . C33 . C34 . 124.02(12) yes
N32 . C33 . H331 . 116.8 no
C34 . C33 . H331 . 119.1 no
C29 . C34 . C33 . 119.15(11) yes
C29 . C34 . H341 . 121.0 no
C33 . C34 . H341 . 119.9 no
C28 . C35 . C36 . 119.69(10) yes
C28 . C35 . H351 . 121.9 no
C36 . C35 . H351 . 118.4 no
C35 . C36 . N25 . 122.37(10) yes
C35 . C36 . H361 . 120.0 no
N25 . C36 . H361 . 117.6 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
C6 . H61 . O16 1_545 137.39 0.989 2.578 3.3725(17) yes
C9 . H91 . O20 1_645 131.76 0.934 2.485 3.1838(17) yes
C26 . H261 . O8 1_455 162.52 0.940 2.562 3.4702(17) yes
C26 . H261 . C9 1_455 155.52 0.940 2.541 3.4188(17) yes
C30 . H301 . O16 1_545 169.02 0.933 2.532 3.4518(17) yes
C36 . H361 . O21 2_577 127.96 0.942 2.537 3.2042(17) yes
N5 . H1 . O8 2_667 136.27 0.847 2.405 3.0734(17) yes
N5 . H1 . O21 . 137.12 0.847 1.974 2.6575(17) yes
N18 . H2 . O22 . 171.81 0.870 2.015 2.8779(17) yes
O22 . H3 . O17 1_455 175.95 0.861 1.891 2.7504(17) yes
N18 . H4 . N32 2_676 160.15 0.899 2.114 2.9755(17) yes
O20 . H5 . N25 2_577 169.46 0.824 1.809 2.6235(17) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/01/13 at 17:47:41
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE N   (   5,X'S) H   (   1,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE N   (  18,X'S) H   (   2,X'S) H   (   4,X'S) 
RIDE O   (  20,X'S) H   (   5,X'S) 
RIDE O   (  22,X'S) H   (   3,X'S) 
RIDE C   (  23,X'S) H   ( 232,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/01/13 at 17:47:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_systematic        'Furosemide - bipyridyl-14butanediol'
_database_code_depnum_ccdc_archive 'CCDC 943034'
