# 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
#  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_Furosemide-Na-trihydrate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Furosemide sodium salt trihydrate'
_chemical_melting_point          '523 K'
_chemical_formula_moiety         'C12 H10 Cl N2 O5 S Na . 3H2O'
_chemical_formula_sum            'C12 H16 Cl N2 Na O8 S'
_chemical_formula_weight         406.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.9184(10)
_cell_length_b                   10.4771(6)
_cell_length_c                   7.8468(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.790(4)
_cell_angle_gamma                90.00
_cell_volume                     1710.96(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2067
_cell_measurement_theta_min      2.7533
_cell_measurement_theta_max      29.0020

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8258
_exptl_absorpt_correction_T_max  0.9071
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6383
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0822
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         24.71
_reflns_number_total             2921
_reflns_number_gt                1797
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0344P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2921
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.29100(4) -0.07974(8) 0.40932(10) 0.0329(2) Uani 1 1 d . . .
Cl1 Cl 0.15017(4) -0.01860(9) 0.53856(12) 0.0494(3) Uani 1 1 d . . .
Na1 Na 0.45809(6) -0.13938(12) 0.39654(18) 0.0441(4) Uani 1 1 d . . .
O1 O 0.35452(10) -0.0627(2) 0.3578(3) 0.0450(7) Uani 1 1 d . . .
O3 O 0.38527(11) 0.3733(2) 0.3496(3) 0.0403(6) Uani 1 1 d . . .
O4 O 0.31455(11) 0.5217(2) 0.4021(3) 0.0459(7) Uani 1 1 d . . .
C4 C 0.26222(15) 0.0748(3) 0.4388(4) 0.0284(8) Uani 1 1 d . . .
N2 N 0.20064(14) 0.4520(3) 0.4937(4) 0.0384(8) Uani 1 1 d . . .
C3 C 0.30082(14) 0.1781(3) 0.4064(4) 0.0276(8) Uani 1 1 d . . .
H3 H 0.3410 0.1612 0.3706 0.033 Uiso 1 1 calc R . .
O2 O 0.24560(11) -0.1517(2) 0.2991(3) 0.0457(7) Uani 1 1 d . . .
O5 O 0.05473(12) 0.4387(2) 0.3456(3) 0.0519(7) Uani 1 1 d . . .
N1 N 0.29887(19) -0.1532(3) 0.5904(4) 0.0447(9) Uani 1 1 d . . .
C2 C 0.28339(14) 0.3040(3) 0.4237(4) 0.0266(8) Uani 1 1 d . . .
C1 C 0.33053(16) 0.4071(3) 0.3904(4) 0.0307(8) Uani 1 1 d . . .
C7 C 0.22023(15) 0.3312(3) 0.4745(4) 0.0297(8) Uani 1 1 d . . .
C6 C 0.18143(15) 0.2261(3) 0.5039(4) 0.0354(9) Uani 1 1 d . . .
H6 H 0.1402 0.2409 0.5343 0.043 Uiso 1 1 calc R . .
C9 C 0.08982(16) 0.5330(4) 0.4290(4) 0.0361(9) Uani 1 1 d . . .
C5 C 0.20147(15) 0.1027(3) 0.4899(4) 0.0323(8) Uani 1 1 d . . .
C8 C 0.14187(15) 0.4937(3) 0.5614(4) 0.0414(9) Uani 1 1 d . . .
H8C H 0.1520 0.5651 0.6382 0.050 Uiso 1 1 calc R . .
H8D H 0.1261 0.4248 0.6283 0.050 Uiso 1 1 calc R . .
C11 C 0.0162(2) 0.6232(5) 0.2442(5) 0.0659(13) Uani 1 1 d . . .
H11 H -0.0084 0.6842 0.1814 0.079 Uiso 1 1 calc R . .
C12 C 0.01013(18) 0.4987(5) 0.2334(5) 0.0642(13) Uani 1 1 d . . .
H12 H -0.0204 0.4568 0.1593 0.077 Uiso 1 1 calc R . .
C10 C 0.06832(19) 0.6453(4) 0.3722(5) 0.0606(12) Uani 1 1 d . . .
H10 H 0.0843 0.7245 0.4091 0.073 Uiso 1 1 calc R . .
O7 O 0.54545(12) -0.2744(3) 0.3625(4) 0.0422(7) Uani 1 1 d . . .
O8 O 0.52517(15) 0.0325(3) 0.3175(4) 0.0477(7) Uani 1 1 d . . .
O6 O 0.41878(16) -0.3183(4) 0.5631(4) 0.0563(8) Uani 1 1 d . . .
H7B H 0.5688(17) -0.245(3) 0.305(5) 0.044(13) Uiso 1 1 d . . .
H1A H 0.2658(18) -0.189(4) 0.604(5) 0.055(14) Uiso 1 1 d . . .
H8B H 0.5530(18) 0.003(4) 0.272(5) 0.053(14) Uiso 1 1 d . . .
H1B H 0.3140(16) -0.102(3) 0.687(4) 0.051(12) Uiso 1 1 d . . .
H8A H 0.501(2) 0.092(5) 0.251(6) 0.103(19) Uiso 1 1 d . . .
H2 H 0.2278(17) 0.509(3) 0.479(5) 0.056(13) Uiso 1 1 d . . .
H7A H 0.574(3) -0.303(5) 0.476(7) 0.14(2) Uiso 1 1 d . . .
H6A H 0.400(3) -0.387(5) 0.527(7) 0.12(2) Uiso 1 1 d . . .
H6B H 0.389(3) -0.284(5) 0.580(7) 0.12(3) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.432(2) . ?
S1 O1 1.439(2) . ?
S1 N1 1.610(3) . ?
S1 C4 1.751(3) . ?
Cl1 C5 1.730(3) . ?
Na1 O1 2.302(3) . ?
Na1 O7 2.348(3) . ?
Na1 O8 2.403(3) . ?
Na1 O6 2.473(3) . ?
Na1 O8 2.501(3) 3_656 ?
Na1 O6 2.699(3) 4 ?
Na1 Na1 3.697(3) 3_656 ?
Na1 H6B 2.62(5) . ?
O3 C1 1.270(4) . ?
O4 C1 1.252(4) . ?
C4 C3 1.389(4) . ?
C4 C5 1.401(4) . ?
N2 C7 1.344(4) . ?
N2 C8 1.455(4) . ?
N2 H2 0.84(3) . ?
C3 C2 1.380(4) . ?
C3 H3 0.9300 . ?
O5 C9 1.358(4) . ?
O5 C12 1.369(4) . ?
N1 H1A 0.80(4) . ?
N1 H1B 0.96(4) . ?
C2 C7 1.446(4) . ?
C2 C1 1.503(4) . ?
C7 C6 1.401(4) . ?
C6 C5 1.367(4) . ?
C6 H6 0.9300 . ?
C9 C10 1.321(5) . ?
C9 C8 1.485(5) . ?
C8 H8C 0.9700 . ?
C8 H8D 0.9700 . ?
C11 C12 1.312(5) . ?
C11 C10 1.425(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
O7 H7B 0.77(3) . ?
O7 H7A 1.06(6) . ?
O8 Na1 2.501(3) 3_656 ?
O8 H8B 0.78(4) . ?
O8 H8A 0.93(5) . ?
O6 Na1 2.699(3) 4_556 ?
O6 H6A 0.86(6) . ?
O6 H6B 0.74(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 118.07(14) . . ?
O2 S1 N1 106.49(18) . . ?
O1 S1 N1 107.00(17) . . ?
O2 S1 C4 110.51(15) . . ?
O1 S1 C4 105.19(14) . . ?
N1 S1 C4 109.36(16) . . ?
O1 Na1 O7 158.18(11) . . ?
O1 Na1 O8 105.70(11) . . ?
O7 Na1 O8 86.60(11) . . ?
O1 Na1 O6 88.61(11) . . ?
O7 Na1 O6 84.69(13) . . ?
O8 Na1 O6 159.82(13) . . ?
O1 Na1 O8 90.41(11) . 3_656 ?
O7 Na1 O8 109.38(12) . 3_656 ?
O8 Na1 O8 82.15(10) . 3_656 ?
O6 Na1 O8 83.63(12) . 3_656 ?
O1 Na1 O6 74.85(10) . 4 ?
O7 Na1 O6 87.42(11) . 4 ?
O8 Na1 O6 90.10(12) . 4 ?
O6 Na1 O6 107.63(10) . 4 ?
O8 Na1 O6 160.89(12) 3_656 4 ?
O1 Na1 Na1 100.41(8) . 3_656 ?
O7 Na1 Na1 100.72(8) . 3_656 ?
O8 Na1 Na1 42.07(7) . 3_656 ?
O6 Na1 Na1 122.34(11) . 3_656 ?
O8 Na1 Na1 40.08(7) 3_656 3_656 ?
O6 Na1 Na1 129.81(11) 4 3_656 ?
O1 Na1 H6B 73.2(12) . . ?
O7 Na1 H6B 101.0(12) . . ?
O8 Na1 H6B 160.8(12) . . ?
O6 Na1 H6B 16.3(12) . . ?
O8 Na1 H6B 78.7(12) 3_656 . ?
O6 Na1 H6B 107.7(13) 4 . ?
Na1 Na1 H6B 118.7(12) 3_656 . ?
S1 O1 Na1 143.44(14) . . ?
C3 C4 C5 116.8(3) . . ?
C3 C4 S1 118.8(2) . . ?
C5 C4 S1 124.4(2) . . ?
C7 N2 C8 127.1(3) . . ?
C7 N2 H2 116(3) . . ?
C8 N2 H2 116(3) . . ?
C2 C3 C4 124.2(3) . . ?
C2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C9 O5 C12 106.0(3) . . ?
S1 N1 H1A 109(3) . . ?
S1 N1 H1B 115(2) . . ?
H1A N1 H1B 112(3) . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 119.1(3) . . ?
C7 C2 C1 122.7(3) . . ?
O4 C1 O3 122.7(3) . . ?
O4 C1 C2 119.5(3) . . ?
O3 C1 C2 117.9(3) . . ?
N2 C7 C6 122.3(3) . . ?
N2 C7 C2 120.9(3) . . ?
C6 C7 C2 116.8(3) . . ?
C5 C6 C7 122.9(3) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C10 C9 O5 109.6(3) . . ?
C10 C9 C8 133.1(4) . . ?
O5 C9 C8 117.3(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 Cl1 118.3(2) . . ?
C4 C5 Cl1 120.7(3) . . ?
N2 C8 C9 114.5(3) . . ?
N2 C8 H8C 108.6 . . ?
C9 C8 H8C 108.6 . . ?
N2 C8 H8D 108.6 . . ?
C9 C8 H8D 108.6 . . ?
H8C C8 H8D 107.6 . . ?
C12 C11 C10 105.6(4) . . ?
C12 C11 H11 127.2 . . ?
C10 C11 H11 127.2 . . ?
C11 C12 O5 111.1(4) . . ?
C11 C12 H12 124.5 . . ?
O5 C12 H12 124.5 . . ?
C9 C10 C11 107.7(4) . . ?
C9 C10 H10 126.2 . . ?
C11 C10 H10 126.2 . . ?
Na1 O7 H7B 112(3) . . ?
Na1 O7 H7A 117(3) . . ?
H7B O7 H7A 106(4) . . ?
Na1 O8 Na1 97.85(10) . 3_656 ?
Na1 O8 H8B 108(3) . . ?
Na1 O8 H8B 123(3) 3_656 . ?
Na1 O8 H8A 111(3) . . ?
Na1 O8 H8A 103(3) 3_656 . ?
H8B O8 H8A 113(4) . . ?
Na1 O6 Na1 123.50(15) . 4_556 ?
Na1 O6 H6A 129(3) . . ?
Na1 O6 H6A 105(4) 4_556 . ?
Na1 O6 H6B 93(4) . . ?
Na1 O6 H6B 95(5) 4_556 . ?
H6A O6 H6B 95(5) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 938492'
#######################################################################
#
#                 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_Furosemide-K-monohydrate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Furosemide potassuium salt monohydrate'
_chemical_melting_point          '523 K'
_chemical_formula_moiety         'C12 H10 Cl N2 O5 S K . H2O'
_chemical_formula_sum            'C12 H12 Cl K N2 O6 S'
_chemical_formula_weight         386.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.8967(10)
_cell_length_b                   11.1734(6)
_cell_length_c                   7.3056(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.346(5)
_cell_angle_gamma                90.00
_cell_volume                     1542.08(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1679
_cell_measurement_theta_min      2.7834
_cell_measurement_theta_max      26.3143

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7346
_exptl_absorpt_correction_T_max  0.8529
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3291
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5512
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         24.71
_reflns_number_total             2636
_reflns_number_gt                2068
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0838P)²+7.2642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2237
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.19354(10) 0.58437(16) 0.4327(3) 0.0482(5) Uani 1 1 d . . .
N2 N 0.1887(3) 0.1335(5) 0.3828(8) 0.0363(13) Uani 1 1 d . . .
H2 H 0.2095 0.0677 0.3552 0.044 Uiso 1 1 calc R . .
C7 C 0.2264(3) 0.2340(6) 0.3661(8) 0.0274(13) Uani 1 1 d . . .
O5 O 0.0432(3) 0.0147(5) 0.2278(7) 0.0490(13) Uani 1 1 d . . .
C8 C 0.1164(3) 0.1243(7) 0.4428(10) 0.0418(17) Uani 1 1 d . . .
H8A H 0.0888 0.1903 0.3924 0.050 Uiso 1 1 calc R . .
H8B H 0.1156 0.1297 0.5752 0.050 Uiso 1 1 calc R . .
C10 C 0.0886(4) -0.1033(8) 0.4408(11) 0.053(2) Uani 1 1 d . . .
H10 H 0.1130 -0.1308 0.5446 0.064 Uiso 1 1 calc R . .
C9 C 0.0848(3) 0.0108(7) 0.3835(9) 0.0365(16) Uani 1 1 d . . .
C11 C 0.0493(5) -0.1737(8) 0.3162(12) 0.059(2) Uani 1 1 d . . .
H11 H 0.0431 -0.2562 0.3206 0.071 Uiso 1 1 calc R . .
C12 C 0.0233(4) -0.1003(8) 0.1927(12) 0.058(2) Uani 1 1 d . . .
H12 H -0.0052 -0.1236 0.0935 0.070 Uiso 1 1 calc R . .
C2 C 0.2967(3) 0.2297(5) 0.3011(7) 0.0258(13) Uani 1 1 d . . .
S1 S 0.35098(9) 0.57437(15) 0.2454(2) 0.0402(5) Uani 1 1 d . . .
O3 O 0.4002(2) 0.1213(4) 0.2309(6) 0.0351(11) Uani 1 1 d . . .
C4 C 0.3017(3) 0.4479(6) 0.3025(8) 0.0287(13) Uani 1 1 d . . .
C6 C 0.1978(3) 0.3472(6) 0.4075(8) 0.0296(14) Uani 1 1 d . . .
H6 H 0.1530 0.3513 0.4573 0.036 Uiso 1 1 calc R . .
C5 C 0.2337(3) 0.4502(5) 0.3768(8) 0.0275(13) Uani 1 1 d . . .
O4 O 0.3040(2) 0.0175(4) 0.2874(6) 0.0387(11) Uani 1 1 d . . .
C3 C 0.3311(3) 0.3362(5) 0.2704(7) 0.0258(13) Uani 1 1 d . . .
H3 H 0.3767 0.3331 0.2256 0.031 Uiso 1 1 calc R . .
C1 C 0.3361(3) 0.1142(6) 0.2705(8) 0.0286(13) Uani 1 1 d . . .
K1 K 0.44053(10) -0.11169(17) 0.2643(3) 0.0577(6) Uani 1 1 d . . .
O6 O 0.5160(3) -0.2466(6) 0.0134(9) 0.0417(13) Uani 1 1 d . . .
O1 O 0.4149(3) 0.5313(5) 0.1672(8) 0.0562(15) Uani 1 1 d . . .
O2 O 0.3573(3) 0.6558(5) 0.3951(8) 0.0590(15) Uani 1 1 d . . .
N1 N 0.3010(5) 0.6395(7) 0.0939(10) 0.059(2) Uani 1 1 d . . .
H1A H 0.306(5) 0.602(9) 0.005(14) 0.071 Uiso 1 1 d . . .
H1B H 0.317(5) 0.706(10) 0.097(12) 0.071 Uiso 1 1 d . . .
H6A H 0.538(5) -0.210(8) -0.050(12) 0.05(3) Uiso 1 1 d . . .
H6B H 0.534(4) -0.281(7) 0.072(10) 0.02(2) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.733(6) . ?
N2 C7 1.336(8) . ?
N2 C8 1.448(8) . ?
N2 H2 0.8600 . ?
C7 C6 1.410(9) . ?
C7 C2 1.422(8) . ?
O5 C12 1.361(10) . ?
O5 C9 1.367(8) . ?
C8 C9 1.464(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C9 1.343(10) . ?
C10 C11 1.401(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.307(12) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C2 C3 1.377(8) . ?
C2 C1 1.509(8) . ?
S1 O2 1.426(5) . ?
S1 O1 1.431(5) . ?
S1 N1 1.611(8) . ?
S1 C4 1.749(6) . ?
O3 C1 1.255(7) . ?
O3 K1 2.722(5) . ?
C4 C3 1.389(9) . ?
C4 C5 1.405(8) . ?
C6 C5 1.359(9) . ?
C6 H6 0.9300 . ?
O4 C1 1.247(7) . ?
O4 K1 2.964(5) . ?
C3 H3 0.9300 . ?
K1 O6 2.781(6) 4_556 ?
K1 O6 2.791(6) . ?
K1 O1 3.126(6) 4_566 ?
K1 O2 3.129(6) 4_565 ?
K1 O2 3.195(6) 1_545 ?
K1 O1 3.195(6) 2_645 ?
K1 K1 4.773(4) 3_656 ?
K1 K1 4.785(2) 4_556 ?
K1 K1 4.785(2) 4 ?
K1 H6B 2.96(7) . ?
O6 K1 2.781(6) 4 ?
O6 H6A 0.75(9) . ?
O6 H6B 0.66(7) . ?
O1 K1 3.126(6) 4_565 ?
O1 K1 3.195(6) 2_655 ?
O2 K1 3.129(6) 4_566 ?
O2 K1 3.195(6) 1_565 ?
N1 H1A 0.78(10) . ?
N1 H1B 0.80(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C8 126.6(6) . . ?
C7 N2 H2 116.7 . . ?
C8 N2 H2 116.7 . . ?
N2 C7 C6 121.7(5) . . ?
N2 C7 C2 120.4(6) . . ?
C6 C7 C2 117.9(5) . . ?
C12 O5 C9 106.1(6) . . ?
N2 C8 C9 110.7(6) . . ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C9 C10 C11 107.8(7) . . ?
C9 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
C10 C9 O5 108.4(6) . . ?
C10 C9 C8 135.4(7) . . ?
O5 C9 C8 116.2(6) . . ?
C12 C11 C10 106.3(8) . . ?
C12 C11 H11 126.8 . . ?
C10 C11 H11 126.8 . . ?
C11 C12 O5 111.4(7) . . ?
C11 C12 H12 124.3 . . ?
O5 C12 H12 124.3 . . ?
C3 C2 C7 118.3(5) . . ?
C3 C2 C1 118.5(5) . . ?
C7 C2 C1 123.2(5) . . ?
O2 S1 O1 117.7(4) . . ?
O2 S1 N1 106.0(4) . . ?
O1 S1 N1 111.3(4) . . ?
O2 S1 C4 111.6(3) . . ?
O1 S1 C4 106.5(3) . . ?
N1 S1 C4 102.8(4) . . ?
C1 O3 K1 100.9(4) . . ?
C3 C4 C5 117.1(5) . . ?
C3 C4 S1 117.9(4) . . ?
C5 C4 S1 125.0(5) . . ?
C5 C6 C7 121.9(5) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C5 C4 120.9(6) . . ?
C6 C5 Cl1 118.1(5) . . ?
C4 C5 Cl1 121.1(5) . . ?
C1 O4 K1 89.5(4) . . ?
C2 C3 C4 123.8(5) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
O4 C1 O3 123.5(6) . . ?
O4 C1 C2 118.9(5) . . ?
O3 C1 C2 117.6(5) . . ?
O3 K1 O6 137.85(19) . 4_556 ?
O3 K1 O6 127.16(19) . . ?
O6 K1 O6 81.95(11) 4_556 . ?
O3 K1 O4 45.37(13) . . ?
O6 K1 O4 132.36(17) 4_556 . ?
O6 K1 O4 139.40(18) . . ?
O3 K1 O1 76.13(14) . 4_566 ?
O6 K1 O1 68.65(18) 4_556 4_566 ?
O6 K1 O1 150.05(18) . 4_566 ?
O4 K1 O1 69.64(14) . 4_566 ?
O3 K1 O2 86.54(14) . 4_565 ?
O6 K1 O2 135.57(19) 4_556 4_565 ?
O6 K1 O2 66.62(17) . 4_565 ?
O4 K1 O2 72.86(14) . 4_565 ?
O1 K1 O2 140.43(16) 4_566 4_565 ?
O3 K1 O2 131.75(15) . 1_545 ?
O6 K1 O2 65.78(17) 4_556 1_545 ?
O6 K1 O2 91.15(17) . 1_545 ?
O4 K1 O2 86.77(14) . 1_545 ?
O1 K1 O2 82.16(14) 4_566 1_545 ?
O2 K1 O2 83.61(15) 4_565 1_545 ?
O3 K1 O1 76.82(14) . 2_645 ?
O6 K1 O1 76.03(17) 4_556 2_645 ?
O6 K1 O1 85.67(15) . 2_645 ?
O4 K1 O1 119.33(14) . 2_645 ?
O1 K1 O1 81.94(15) 4_566 2_645 ?
O2 K1 O1 128.65(16) 4_565 2_645 ?
O2 K1 O1 141.74(16) 1_545 2_645 ?
O3 K1 K1 71.96(11) . 3_656 ?
O6 K1 K1 66.41(16) 4_556 3_656 ?
O6 K1 K1 121.13(13) . 3_656 ?
O4 K1 K1 95.74(11) . 3_656 ?
O1 K1 K1 41.51(11) 4_566 3_656 ?
O2 K1 K1 157.37(12) 4_565 3_656 ?
O2 K1 K1 115.86(12) 1_545 3_656 ?
O1 K1 K1 40.43(11) 2_645 3_656 ?
O3 K1 K1 132.93(10) . 4_556 ?
O6 K1 K1 30.88(12) 4_556 4_556 ?
O6 K1 K1 99.30(16) . 4_556 ?
O4 K1 K1 104.80(9) . 4_556 ?
O1 K1 K1 57.58(9) 4_566 4_556 ?
O2 K1 K1 123.18(12) 4_565 4_556 ?
O2 K1 K1 40.32(11) 1_545 4_556 ?
O1 K1 K1 102.64(10) 2_645 4_556 ?
K1 K1 K1 78.19(3) 3_656 4_556 ?
O3 K1 K1 123.68(10) . 4 ?
O6 K1 K1 97.04(17) 4_556 4 ?
O6 K1 K1 30.76(12) . 4 ?
O4 K1 K1 111.94(9) . 4 ?
O1 K1 K1 155.11(12) 4_566 4 ?
O2 K1 K1 41.34(10) 4_565 4 ?
O2 K1 K1 73.26(11) 1_545 4 ?
O1 K1 K1 115.30(10) 2_645 4 ?
K1 K1 K1 151.67(4) 3_656 4 ?
K1 K1 K1 99.53(7) 4_556 4 ?
O3 K1 H6B 137.4(14) . . ?
O6 K1 H6B 69.2(14) 4_556 . ?
O6 K1 H6B 12.7(14) . . ?
O4 K1 H6B 150.0(14) . . ?
O1 K1 H6B 137.5(14) 4_566 . ?
O2 K1 H6B 77.5(14) 4_565 . ?
O2 K1 H6B 85.8(14) 1_545 . ?
O1 K1 H6B 82.9(14) 2_645 . ?
K1 K1 H6B 113.6(14) 3_656 . ?
K1 K1 H6B 87.8(14) 4_556 . ?
K1 K1 H6B 38.3(14) 4 . ?
K1 O6 K1 118.4(2) 4 . ?
K1 O6 H6A 101(7) 4 . ?
K1 O6 H6A 114(7) . . ?
K1 O6 H6B 110(6) 4 . ?
K1 O6 H6B 99(6) . . ?
H6A O6 H6B 115(9) . . ?
S1 O1 K1 115.5(3) . 4_565 ?
S1 O1 K1 146.3(3) . 2_655 ?
K1 O1 K1 98.06(15) 4_565 2_655 ?
S1 O2 K1 126.3(3) . 4_566 ?
S1 O2 K1 108.8(3) . 1_565 ?
K1 O2 K1 98.33(15) 4_566 1_565 ?
S1 N1 H1A 105(8) . . ?
S1 N1 H1B 100(7) . . ?
H1A N1 H1B 118(10) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.104
_database_code_depnum_ccdc_archive 'CCDC 938493'
