# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2011
data_global
_journal_name_full               'Chemical Science'

_journal_coden_Cambridge         1475
_journal_year                    2010

_publ_contact_author_name        'Gale, Philip'
_publ_contact_author_email       philip.gale@soton.ac.uk

_publ_section_title              
;
Structurally simple lipid bilayer transport
agents for chloride and bicarbonate
;
loop_
_publ_author_name
P.Gale
J.Davis
C.Haynes
M.Light
S.Moore
C.Tong
W.Harrell

# Attachment '2010sot0773-2010sot0813-combined.cif'

data_2010sot0773
_database_code_depnum_ccdc_archive 'CCDC 791977'
#TrackingRef '2010sot0773-2010sot0813-combined.cif'

_chemical_compound_source        'Stephen Moore'
_database_code_CSD               10ST0773

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 N2 O'
_chemical_formula_weight         206.28

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pccn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   21.8777(7)
_cell_length_b                   24.4332(8)
_cell_length_c                   8.9667(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4793.1(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    56488
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1792
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9854
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55376
_diffrn_reflns_av_R_equivalents  0.1849
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4234
_reflns_number_gt                2561
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Disorder in the alkyl chain was treated using thermal parameter
restraints and constraints and geometry restraints.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+13.9543P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4234
_refine_ls_number_parameters     287
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.1841
_refine_ls_R_factor_gt           0.1143
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.002

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
C1 C -0.08080(19) 0.13096(17) 0.6504(5) 0.0486(12) Uani 1 1 d . . .
H1 H -0.0953 0.1533 0.7295 0.058 Uiso 1 1 calc R . .
C2 C -0.1004(2) 0.07702(17) 0.6400(6) 0.0556(13) Uani 1 1 d . . .
H2 H -0.1279 0.0627 0.7121 0.067 Uiso 1 1 calc R . .
C3 C -0.0801(2) 0.04440(18) 0.5259(5) 0.0521(13) Uani 1 1 d . . .
H3 H -0.0928 0.0073 0.5192 0.063 Uiso 1 1 calc R . .
C4 C -0.0410(2) 0.06607(17) 0.4214(4) 0.0476(12) Uani 1 1 d . . .
H4 H -0.0275 0.0438 0.3410 0.057 Uiso 1 1 calc R . .
C5 C -0.02108(19) 0.11938(16) 0.4307(4) 0.0412(11) Uani 1 1 d . . .
H5 H 0.0060 0.1335 0.3574 0.049 Uiso 1 1 calc R . .
C6 C -0.04058(16) 0.15258(15) 0.5473(4) 0.0322(9) Uani 1 1 d . . .
C7 C 0.00033(17) 0.24251(15) 0.4668(3) 0.0292(9) Uani 1 1 d . . .
N2A N 0.02347(14) 0.28941(12) 0.5210(3) 0.0367(8) Uani 0.482(5) 1 d PDU A 1
H2A H 0.0344 0.2920 0.6152 0.044 Uiso 0.482(5) 1 calc PR A 1
C8A C 0.0302(4) 0.3365(2) 0.4189(7) 0.0385(12) Uani 0.482(5) 1 d PDU A 1
H8A1 H -0.0099 0.3457 0.3743 0.046 Uiso 0.482(5) 1 calc PR A 1
H8A2 H 0.0588 0.3271 0.3372 0.046 Uiso 0.482(5) 1 calc PR A 1
C9A C 0.0542(4) 0.3846(2) 0.5043(8) 0.0380(9) Uani 0.482(5) 1 d PDU A 1
H9A1 H 0.0779 0.3696 0.5893 0.046 Uiso 0.482(5) 1 calc PR A 1
H9A2 H 0.0184 0.4035 0.5475 0.046 Uiso 0.482(5) 1 calc PR A 1
C10A C 0.0894(5) 0.4336(4) 0.2655(7) 0.061(2) Uani 0.482(5) 1 d PDU A 1
H10A H 0.1212 0.4587 0.2303 0.092 Uiso 0.482(5) 1 calc PR A 1
H10B H 0.0491 0.4480 0.2384 0.092 Uiso 0.482(5) 1 calc PR A 1
H10C H 0.0951 0.3977 0.2192 0.092 Uiso 0.482(5) 1 calc PR A 1
C11A C 0.0935(4) 0.4281(2) 0.4332(7) 0.0449(13) Uani 0.482(5) 1 d PDU A 1
H11A H 0.1362 0.4149 0.4505 0.054 Uiso 0.482(5) 1 calc PR A 1
C12A C 0.0910(6) 0.4822(3) 0.5154(10) 0.0622(15) Uani 0.482(5) 1 d PDU A 1
H12A H 0.0995 0.4761 0.6214 0.093 Uiso 0.482(5) 1 calc PR A 1
H12B H 0.0503 0.4983 0.5041 0.093 Uiso 0.482(5) 1 calc PR A 1
H12C H 0.1217 0.5072 0.4737 0.093 Uiso 0.482(5) 1 calc PR A 1
N2B N 0.02347(14) 0.28941(12) 0.5210(3) 0.0367(8) Uani 0.518(5) 1 d PDU A 2
H2B H 0.0176 0.2961 0.6163 0.044 Uiso 0.518(5) 1 calc PR A 2
C8B C 0.0575(3) 0.3303(2) 0.4360(7) 0.0385(12) Uani 0.518(5) 1 d PDU A 2
H8B1 H 0.0403 0.3326 0.3340 0.046 Uiso 0.518(5) 1 calc PR A 2
H8B2 H 0.1006 0.3184 0.4273 0.046 Uiso 0.518(5) 1 calc PR A 2
C9B C 0.0556(4) 0.3857(2) 0.5059(8) 0.0380(9) Uani 0.518(5) 1 d PDU A 2
H9B1 H 0.0860 0.3865 0.5878 0.046 Uiso 0.518(5) 1 calc PR A 2
H9B2 H 0.0148 0.3908 0.5512 0.046 Uiso 0.518(5) 1 calc PR A 2
C10B C 0.1185(4) 0.4216(4) 0.2895(8) 0.061(2) Uani 0.518(5) 1 d PDU A 2
H10D H 0.1081 0.3882 0.2347 0.092 Uiso 0.518(5) 1 calc PR A 2
H10E H 0.1574 0.4163 0.3419 0.092 Uiso 0.518(5) 1 calc PR A 2
H10F H 0.1224 0.4522 0.2194 0.092 Uiso 0.518(5) 1 calc PR A 2
C11B C 0.0681(3) 0.4343(2) 0.4030(7) 0.0449(13) Uani 0.518(5) 1 d PDU A 2
H11B H 0.0297 0.4434 0.3478 0.054 Uiso 0.518(5) 1 calc PR A 2
C12B C 0.0868(6) 0.4837(3) 0.4967(11) 0.0622(15) Uani 0.518(5) 1 d PDU A 2
H12D H 0.0578 0.4883 0.5792 0.093 Uiso 0.518(5) 1 calc PR A 2
H12E H 0.0866 0.5166 0.4343 0.093 Uiso 0.518(5) 1 calc PR A 2
H12F H 0.1279 0.4779 0.5368 0.093 Uiso 0.518(5) 1 calc PR A 2
N1 N -0.01938(14) 0.20632(13) 0.5704(3) 0.0352(8) Uani 1 1 d . A .
H1A H -0.0189 0.2178 0.6634 0.042 Uiso 1 1 calc R . .
O1 O -0.00341(14) 0.23315(11) 0.3311(3) 0.0485(8) Uani 1 1 d . A .
C13 C 0.1643(2) 0.38188(17) 0.8744(5) 0.0487(12) Uani 1 1 d . . .
H13 H 0.1556 0.4110 0.9413 0.058 Uiso 1 1 calc R . .
C14 C 0.1392(2) 0.33039(19) 0.8988(5) 0.0555(13) Uani 1 1 d . . .
H14 H 0.1134 0.3246 0.9825 0.067 Uiso 1 1 calc R . .
C15 C 0.1512(2) 0.2878(2) 0.8030(6) 0.0679(16) Uani 1 1 d . . .
H15 H 0.1342 0.2526 0.8206 0.082 Uiso 1 1 calc R . .
C16 C 0.1883(2) 0.29674(18) 0.6808(7) 0.0667(16) Uani 1 1 d . . .
H16 H 0.1961 0.2677 0.6129 0.080 Uiso 1 1 calc R . .
C17 C 0.21398(19) 0.34732(18) 0.6567(5) 0.0502(12) Uani 1 1 d . . .
H17 H 0.2401 0.3526 0.5734 0.060 Uiso 1 1 calc R . .
C18 C 0.20228(19) 0.39095(17) 0.7526(4) 0.0406(11) Uani 1 1 d . . .
C19 C 0.23562(17) 0.48580(16) 0.8099(4) 0.0356(10) Uani 1 1 d . . .
N4 N 0.25699(15) 0.53111(12) 0.7440(3) 0.0388(9) Uani 1 1 d D . .
H4A H 0.2616 0.5317 0.6465 0.047 Uiso 1 1 calc R . .
C20 C 0.27282(18) 0.57948(14) 0.8311(4) 0.0357(10) Uani 1 1 d D . .
H20A H 0.3043 0.5696 0.9057 0.043 Uiso 1 1 calc R . .
H20B H 0.2362 0.5924 0.8855 0.043 Uiso 1 1 calc R . .
C21 C 0.29664(18) 0.62503(14) 0.7343(4) 0.0380(10) Uani 1 1 d D . .
H21A H 0.2651 0.6345 0.6595 0.046 Uiso 1 1 calc R . .
H21B H 0.3331 0.6118 0.6797 0.046 Uiso 1 1 calc R . .
C22 C 0.3644(2) 0.66608(18) 0.9339(5) 0.0585(14) Uani 1 1 d D . .
H22A H 0.3516 0.6371 1.0026 0.088 Uiso 1 1 calc R . .
H22B H 0.3725 0.6997 0.9902 0.088 Uiso 1 1 calc R . .
H22C H 0.4016 0.6547 0.8815 0.088 Uiso 1 1 calc R . .
C23 C 0.31381(18) 0.67661(14) 0.8210(4) 0.0434(11) Uani 1 1 d D . .
H23 H 0.2768 0.6891 0.8768 0.052 Uiso 1 1 calc R . .
C24 C 0.3321(2) 0.72202(16) 0.7130(5) 0.0619(14) Uani 1 1 d D . .
H24A H 0.2988 0.7285 0.6421 0.093 Uiso 1 1 calc R . .
H24B H 0.3690 0.7111 0.6587 0.093 Uiso 1 1 calc R . .
H24C H 0.3403 0.7557 0.7690 0.093 Uiso 1 1 calc R . .
N3 N 0.22745(16) 0.44215(13) 0.7175(3) 0.0454(10) Uani 1 1 d . . .
H3A H 0.2394 0.4466 0.6246 0.054 Uiso 1 1 calc R . .
O2 O 0.22449(12) 0.48440(11) 0.9462(3) 0.0405(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.055(3) 0.042(3) 0.049(2) 0.002(2) 0.017(2) 0.010(2)
C2 0.050(3) 0.038(2) 0.079(3) 0.018(2) 0.009(3) 0.006(2)
C3 0.056(3) 0.036(2) 0.064(3) 0.001(2) -0.012(3) 0.002(2)
C4 0.069(3) 0.038(2) 0.036(2) -0.0051(19) -0.011(2) 0.008(2)
C5 0.053(3) 0.041(2) 0.030(2) -0.0042(19) -0.0002(19) 0.004(2)
C6 0.031(2) 0.037(2) 0.0290(18) -0.0004(17) -0.0018(17) 0.0069(18)
C7 0.0356(19) 0.034(2) 0.0183(16) 0.0014(15) 0.0015(16) 0.0051(17)
N2A 0.0494(18) 0.0440(17) 0.0166(13) 0.0042(13) 0.0037(13) -0.0060(15)
C8A 0.046(3) 0.044(2) 0.0263(18) 0.0030(17) 0.005(2) -0.003(2)
C9A 0.0386(18) 0.0429(18) 0.0325(16) 0.0037(15) -0.0055(16) -0.0049(16)
C10A 0.071(5) 0.056(4) 0.056(3) 0.032(3) -0.004(4) -0.011(4)
C11A 0.049(3) 0.045(2) 0.041(2) 0.009(2) -0.006(2) -0.004(2)
C12A 0.057(3) 0.059(3) 0.070(3) 0.007(3) -0.010(3) -0.021(2)
N2B 0.0494(18) 0.0440(17) 0.0166(13) 0.0042(13) 0.0037(13) -0.0060(15)
C8B 0.046(3) 0.044(2) 0.0263(18) 0.0030(17) 0.005(2) -0.003(2)
C9B 0.0386(18) 0.0429(18) 0.0325(16) 0.0037(15) -0.0055(16) -0.0049(16)
C10B 0.071(5) 0.056(4) 0.056(3) 0.032(3) -0.004(4) -0.011(4)
C11B 0.049(3) 0.045(2) 0.041(2) 0.009(2) -0.006(2) -0.004(2)
C12B 0.057(3) 0.059(3) 0.070(3) 0.007(3) -0.010(3) -0.021(2)
N1 0.050(2) 0.0378(18) 0.0179(14) -0.0005(14) 0.0065(14) -0.0059(16)
O1 0.089(2) 0.0403(17) 0.0167(12) 0.0006(11) -0.0009(14) 0.0024(16)
C13 0.070(3) 0.040(2) 0.037(2) -0.004(2) -0.010(2) -0.006(2)
C14 0.054(3) 0.053(3) 0.060(3) 0.009(2) -0.016(2) -0.019(2)
C15 0.049(3) 0.046(3) 0.109(4) 0.015(3) -0.022(3) -0.007(2)
C16 0.046(3) 0.032(2) 0.122(5) -0.019(3) -0.017(3) 0.005(2)
C17 0.043(2) 0.048(3) 0.060(3) -0.008(2) -0.008(2) 0.007(2)
C18 0.050(2) 0.043(2) 0.0293(19) -0.0020(18) -0.0140(19) 0.004(2)
C19 0.044(2) 0.041(2) 0.0220(17) 0.0001(17) 0.0011(17) 0.0035(19)
N4 0.057(2) 0.0383(18) 0.0208(14) -0.0018(14) 0.0022(15) 0.0005(17)
C20 0.048(2) 0.037(2) 0.0222(17) -0.0026(17) -0.0016(18) 0.0049(19)
C21 0.041(2) 0.040(2) 0.033(2) 0.0043(18) 0.0014(18) 0.0030(19)
C22 0.068(3) 0.052(3) 0.056(3) -0.016(2) 0.003(3) -0.013(2)
C23 0.043(2) 0.036(2) 0.051(2) -0.008(2) 0.014(2) 0.004(2)
C24 0.070(3) 0.039(3) 0.077(3) 0.003(2) 0.025(3) -0.001(2)
N3 0.073(3) 0.041(2) 0.0225(15) -0.0019(15) 0.0019(17) -0.0048(19)
O2 0.0574(17) 0.0435(16) 0.0205(12) -0.0014(12) -0.0001(13) 0.0019(14)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.381(5) . ?
C1 C2 1.389(6) . ?
C2 C3 1.371(6) . ?
C3 C4 1.374(6) . ?
C4 C5 1.376(6) . ?
C5 C6 1.391(5) . ?
C6 N1 1.408(5) . ?
C7 O1 1.241(4) . ?
C7 N2A 1.344(5) . ?
C7 N1 1.353(4) . ?
N2A C8A 1.478(6) . ?
C8A C9A 1.498(7) . ?
C9A C11A 1.509(6) . ?
C10A C11A 1.512(7) . ?
C11A C12A 1.514(7) . ?
C8B C9B 1.492(6) . ?
C9B C11B 1.528(6) . ?
C10B C11B 1.533(7) . ?
C11B C12B 1.527(7) . ?
C13 C18 1.390(6) . ?
C13 C14 1.391(6) . ?
C14 C15 1.375(7) . ?
C15 C16 1.380(7) . ?
C16 C17 1.375(6) . ?
C17 C18 1.393(6) . ?
C18 N3 1.403(5) . ?
C19 O2 1.247(4) . ?
C19 N4 1.339(5) . ?
C19 N3 1.362(5) . ?
N4 C20 1.458(4) . ?
C20 C21 1.504(4) . ?
C21 C23 1.528(5) . ?
C22 C23 1.522(5) . ?
C23 C24 1.526(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
C6 C1 C2 121.0(4) . . ?
C3 C2 C1 120.1(4) . . ?
C2 C3 C4 119.1(4) . . ?
C3 C4 C5 121.3(4) . . ?
C4 C5 C6 120.0(4) . . ?
C1 C6 C5 118.4(4) . . ?
C1 C6 N1 117.9(3) . . ?
C5 C6 N1 123.6(3) . . ?
O1 C7 N2A 122.4(3) . . ?
O1 C7 N1 122.1(3) . . ?
N2A C7 N1 115.4(3) . . ?
C7 N2A C8A 118.5(3) . . ?
N2A C8A C9A 109.2(5) . . ?
C8A C9A C11A 122.4(5) . . ?
C9A C11A C10A 116.7(6) . . ?
C9A C11A C12A 112.9(6) . . ?
C10A C11A C12A 113.8(6) . . ?
C8B C9B C11B 116.5(5) . . ?
C12B C11B C9B 109.3(6) . . ?
C12B C11B C10B 109.4(6) . . ?
C9B C11B C10B 111.8(6) . . ?
C7 N1 C6 127.9(3) . . ?
C18 C13 C14 120.3(4) . . ?
C15 C14 C13 120.7(5) . . ?
C14 C15 C16 119.3(5) . . ?
C17 C16 C15 120.4(5) . . ?
C16 C17 C18 121.1(5) . . ?
C13 C18 C17 118.2(4) . . ?
C13 C18 N3 123.6(4) . . ?
C17 C18 N3 118.2(4) . . ?
O2 C19 N4 121.6(3) . . ?
O2 C19 N3 123.3(4) . . ?
N4 C19 N3 115.1(3) . . ?
C19 N4 C20 121.1(3) . . ?
N4 C20 C21 111.9(3) . . ?
C20 C21 C23 113.7(3) . . ?
C22 C23 C24 110.7(3) . . ?
C22 C23 C21 112.2(3) . . ?
C24 C23 C21 110.0(3) . . ?
C19 N3 C18 127.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2A H2A O1 0.88 2.19 2.895(4) 136.4 7_566
N2B H2B O1 0.88 2.11 2.895(4) 149.0 7_566
N1 H1A O1 0.88 1.95 2.788(4) 158.0 7_566
N4 H4A O2 0.88 2.16 2.933(4) 146.5 8_655
N3 H3A O2 0.88 2.01 2.844(4) 158.1 8_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.058

_iucr_refine_instruction_details 
;
TITL new in Pccn
CELL 0.71073 21.8777 24.4332 8.9667 90.000 90.000 90.000
ZERR 16.00 0.0007 0.0008 0.0002 0.000 0.000 0.000
LATT 1
SYMM 1/2 - X, 1/2 - Y, Z
SYMM - X, 1/2 + Y, 1/2 - Z
SYMM 1/2 + X, - Y, 1/2 - Z
SFAC C H N O
UNIT 192 288 32 16
MERG 2
SHEL 7 0.84
ACTA 55
TEMP -153
HTAB
HTAB N2A O1_$1
EQIV $1 [ x, -y+1/2, z+1/2 ]
HTAB N2B O1_$1
HTAB N1 O1_$1

HTAB N4 O2_$2
EQIV $2 [ -x+1/2, y, z-1/2 ]
HTAB N3 O2_$2

SIZE 0.2 0.1 0.04
EADP N2A N2B
EXYZ N2A N2B
EADP C8A C8B
EADP C9A C9B
EADP C10A C10B
EADP C11A C11B
EADP C12A C12B
SIMU 0.01 N2A C8A C9A C10A C11A C12A N2B C8B C9B C10B C11B C12B
DFIX 1.54 C22 C23 C23 C24
FMAP 2
BUMP
PLAN 20
BOND
L.S. 14
DAMP 500.00 15.00
WGHT 0.000000 13.954300
FVAR 0.21332 0.48246
MOLE 1
C1 1 -0.080804 0.130956 0.650356 11.00000 0.05508 0.04182 =
0.04898 0.00237 0.01730 0.01013
AFIX 43
H1 2 -0.095302 0.153312 0.729492 11.00000 -1.20000
AFIX 0
C2 1 -0.100383 0.077021 0.640036 11.00000 0.05004 0.03831 =
0.07858 0.01830 0.00945 0.00610
AFIX 43
H2 2 -0.127890 0.062707 0.712142 11.00000 -1.20000
AFIX 0
C3 1 -0.080060 0.044396 0.525883 11.00000 0.05649 0.03559 =
0.06418 0.00104 -0.01190 0.00217
AFIX 43
H3 2 -0.092808 0.007310 0.519151 11.00000 -1.20000
AFIX 0
C4 1 -0.041004 0.066066 0.421353 11.00000 0.06861 0.03845 =
0.03570 -0.00509 -0.01054 0.00827
AFIX 43
H4 2 -0.027485 0.043788 0.341031 11.00000 -1.20000
AFIX 0
C5 1 -0.021080 0.119385 0.430679 11.00000 0.05279 0.04082 =
0.02998 -0.00419 -0.00023 0.00419
AFIX 43
H5 2 0.006010 0.133521 0.357382 11.00000 -1.20000
AFIX 0
C6 1 -0.040581 0.152584 0.547340 11.00000 0.03106 0.03654 =
0.02897 -0.00039 -0.00175 0.00685
C7 1 0.000328 0.242510 0.466831 11.00000 0.03563 0.03373 =
0.01834 0.00135 0.00154 0.00513
PART 1
SAME 0.01 N4 > C24
N2A 3 0.023470 0.289408 0.520976 21.00000 0.04940 0.04403 =
0.01664 0.00419 0.00372 -0.00599
AFIX 43
H2A 2 0.034391 0.292022 0.615163 21.00000 -1.20000
AFIX 0
C8A 1 0.030185 0.336515 0.418870 21.00000 0.04555 0.04374 =
0.02632 0.00303 0.00537 -0.00263
AFIX 23
H8A1 2 -0.009908 0.345739 0.374270 21.00000 -1.20000
H8A2 2 0.058751 0.327070 0.337199 21.00000 -1.20000
AFIX 0
C9A 1 0.054242 0.384591 0.504339 21.00000 0.03862 0.04294 =
0.03245 0.00369 -0.00553 -0.00493
AFIX 23
H9A1 2 0.077862 0.369649 0.589257 21.00000 -1.20000
H9A2 2 0.018354 0.403529 0.547467 21.00000 -1.20000
AFIX 0
C10A 1 0.089354 0.433619 0.265520 21.00000 0.07145 0.05580 =
0.05583 0.03182 -0.00444 -0.01073
AFIX 33
H10A 2 0.121157 0.458731 0.230287 21.00000 -1.50000
H10B 2 0.049065 0.448044 0.238378 21.00000 -1.50000
H10C 2 0.095131 0.397653 0.219236 21.00000 -1.50000
AFIX 0
C11A 1 0.093534 0.428105 0.433186 21.00000 0.04853 0.04511 =
0.04101 0.00943 -0.00581 -0.00361
AFIX 13
H11A 2 0.136221 0.414921 0.450494 21.00000 -1.20000
AFIX 0
C12A 1 0.091027 0.482185 0.515351 21.00000 0.05744 0.05926 =
0.07001 0.00728 -0.00951 -0.02083
AFIX 33
H12A 2 0.099547 0.476125 0.621371 21.00000 -1.50000
H12B 2 0.050257 0.498283 0.504131 21.00000 -1.50000
H12C 2 0.121653 0.507155 0.473740 21.00000 -1.50000
AFIX 0
PART 2
SAME 0.01 N4 > C24
N2B 3 0.023470 0.289408 0.520976 -21.00000 0.04940 0.04403 =
0.01664 0.00419 0.00372 -0.00599
AFIX 43
H2B 2 0.017570 0.296112 0.616322 -21.00000 -1.20000
AFIX 0
C8B 1 0.057541 0.330287 0.435962 -21.00000 0.04555 0.04374 =
0.02632 0.00303 0.00537 -0.00263
AFIX 23
H8B1 2 0.040349 0.332557 0.334019 -21.00000 -1.20000
H8B2 2 0.100650 0.318386 0.427289 -21.00000 -1.20000
AFIX 0
C9B 1 0.055620 0.385698 0.505859 -21.00000 0.03862 0.04294 =
0.03245 0.00369 -0.00553 -0.00493
AFIX 23
H9B1 2 0.085951 0.386549 0.587763 -21.00000 -1.20000
H9B2 2 0.014756 0.390780 0.551216 -21.00000 -1.20000
AFIX 0
C10B 1 0.118535 0.421610 0.289525 -21.00000 0.07145 0.05580 =
0.05583 0.03182 -0.00444 -0.01073
AFIX 33
H10D 2 0.108078 0.388195 0.234720 -21.00000 -1.50000
H10E 2 0.157408 0.416337 0.341896 -21.00000 -1.50000
H10F 2 0.122371 0.452185 0.219406 -21.00000 -1.50000
AFIX 0
C11B 1 0.068093 0.434301 0.402995 -21.00000 0.04853 0.04511 =
0.04101 0.00943 -0.00581 -0.00361
AFIX 13
H11B 2 0.029693 0.443398 0.347811 -21.00000 -1.20000
AFIX 0
C12B 1 0.086772 0.483726 0.496702 -21.00000 0.05744 0.05926 =
0.07001 0.00728 -0.00951 -0.02083
AFIX 33
H12D 2 0.057824 0.488348 0.579152 -21.00000 -1.50000
H12E 2 0.086554 0.516642 0.434253 -21.00000 -1.50000
H12F 2 0.127926 0.477910 0.536844 -21.00000 -1.50000
AFIX 0
PART 0
N1 3 -0.019380 0.206322 0.570385 11.00000 0.05000 0.03784 =
0.01792 -0.00047 0.00648 -0.00591
AFIX 43
H1A 2 -0.018887 0.217759 0.663439 11.00000 -1.20000
AFIX 0
O1 4 -0.003412 0.233151 0.331074 11.00000 0.08862 0.04027 =
0.01674 0.00064 -0.00092 0.00238
MOLE 2
C13 1 0.164350 0.381880 0.874417 11.00000 0.06951 0.03989 =
0.03682 -0.00438 -0.01025 -0.00607
AFIX 43
H13 2 0.155579 0.410979 0.941349 11.00000 -1.20000
AFIX 0
C14 1 0.139187 0.330388 0.898775 11.00000 0.05435 0.05259 =
0.05959 0.00934 -0.01614 -0.01863
AFIX 43
H14 2 0.113410 0.324570 0.982548 11.00000 -1.20000
AFIX 0
C15 1 0.151208 0.287815 0.802960 11.00000 0.04875 0.04619 =
0.10886 0.01458 -0.02181 -0.00718
AFIX 43
H15 2 0.134178 0.252640 0.820605 11.00000 -1.20000
AFIX 0
C16 1 0.188298 0.296735 0.680806 11.00000 0.04613 0.03159 =
0.12233 -0.01922 -0.01685 0.00479
AFIX 43
H16 2 0.196127 0.267720 0.612917 11.00000 -1.20000
AFIX 0
C17 1 0.213982 0.347323 0.656732 11.00000 0.04306 0.04751 =
0.06009 -0.00823 -0.00834 0.00653
AFIX 43
H17 2 0.240136 0.352609 0.573393 11.00000 -1.20000
AFIX 0
C18 1 0.202277 0.390951 0.752560 11.00000 0.04971 0.04264 =
0.02935 -0.00203 -0.01402 0.00364
C19 1 0.235617 0.485803 0.809894 11.00000 0.04403 0.04062 =
0.02203 0.00008 0.00115 0.00351
N4 3 0.256986 0.531113 0.744038 11.00000 0.05736 0.03827 =
0.02076 -0.00184 0.00225 0.00054
AFIX 43
H4A 2 0.261551 0.531705 0.646545 11.00000 -1.20000
AFIX 0
C20 1 0.272821 0.579483 0.831054 11.00000 0.04808 0.03670 =
0.02221 -0.00261 -0.00157 0.00488
AFIX 23
H20A 2 0.304292 0.569604 0.905682 11.00000 -1.20000
H20B 2 0.236177 0.592378 0.885474 11.00000 -1.20000
AFIX 0
C21 1 0.296638 0.625030 0.734284 11.00000 0.04108 0.04016 =
0.03275 0.00434 0.00139 0.00300
AFIX 23
H21A 2 0.265080 0.634537 0.659515 11.00000 -1.20000
H21B 2 0.333098 0.611802 0.679719 11.00000 -1.20000
AFIX 0
C22 1 0.364394 0.666078 0.933877 11.00000 0.06795 0.05167 =
0.05575 -0.01561 0.00279 -0.01286
AFIX 33
H22A 2 0.351621 0.637069 1.002619 11.00000 -1.50000
H22B 2 0.372528 0.699670 0.990206 11.00000 -1.50000
H22C 2 0.401608 0.654715 0.881514 11.00000 -1.50000
AFIX 0
C23 1 0.313814 0.676607 0.820985 11.00000 0.04335 0.03631 =
0.05061 -0.00768 0.01370 0.00426
AFIX 13
H23 2 0.276794 0.689126 0.876796 11.00000 -1.20000
AFIX 0
C24 1 0.332144 0.722021 0.713050 11.00000 0.06994 0.03878 =
0.07708 0.00310 0.02456 -0.00074
AFIX 33
H24A 2 0.298848 0.728466 0.642078 11.00000 -1.50000
H24B 2 0.369042 0.711079 0.658724 11.00000 -1.50000
H24C 2 0.340314 0.755684 0.769032 11.00000 -1.50000
AFIX 0
N3 3 0.227451 0.442151 0.717513 11.00000 0.07292 0.04079 =
0.02246 -0.00187 0.00190 -0.00477
AFIX 43
H3A 2 0.239419 0.446616 0.624610 11.00000 -1.20000
AFIX 0
O2 4 0.224493 0.484398 0.946185 11.00000 0.05742 0.04355 =
0.02046 -0.00138 -0.00010 0.00191
HKLF 4

REM new in Pccn
REM R1 = 0.1143 for 2561 Fo > 4sig(Fo) and 0.1841 for all 4234 data
REM 287 parameters refined using 189 restraints

END

WGHT 0.0000 13.6119
REM Highest difference peak 0.247, deepest hole -0.261, 1-sigma level 0.058
Q1 1 0.1755 0.4024 0.9543 11.00000 0.05 0.23
Q2 1 0.0451 0.3930 0.6103 11.00000 0.05 0.23
Q3 1 0.1931 0.3778 0.6586 11.00000 0.05 0.22
Q4 1 0.0300 0.2287 0.3983 11.00000 0.05 0.21
Q5 1 0.1034 0.4099 0.2127 11.00000 0.05 0.21
Q6 1 0.2839 0.5230 0.6579 11.00000 0.05 0.21
Q7 1 0.2242 0.3014 0.7525 11.00000 0.05 0.21
Q8 1 0.0505 0.4401 0.2815 11.00000 0.05 0.21
Q9 1 0.1683 0.2289 0.8973 11.00000 0.05 0.21
Q10 1 0.3900 0.7194 0.7059 11.00000 0.05 0.20
Q11 1 0.0618 0.2899 0.9872 11.00000 0.05 0.20
Q12 1 0.2121 0.3899 0.8450 11.00000 0.05 0.20
Q13 1 -0.1425 0.0191 0.6950 11.00000 0.05 0.20
Q14 1 0.3691 0.7033 0.9266 11.00000 0.05 0.20
Q15 1 0.0972 0.3332 0.3940 11.00000 0.05 0.19
Q16 1 0.1604 0.3781 0.3002 11.00000 0.05 0.19
Q17 1 0.1568 0.2901 1.0391 11.00000 0.05 0.19
Q18 1 0.0729 0.3198 0.3098 11.00000 0.05 0.19
Q19 1 0.2500 0.7500 0.6599 10.50000 0.05 0.18
Q20 1 0.1052 0.3589 0.5095 11.00000 0.05 0.18
;

#==END

data_2010sot0813
_database_code_depnum_ccdc_archive 'CCDC 793790'
#TrackingRef '2010sot0773-2010sot0813-combined.cif'

_chemical_compound_source        'Calley Haynes'
_database_code_CSD               10ST0813

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N3 S'
_chemical_formula_weight         261.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/a
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   29.2158(5)
_cell_length_b                   29.2158(5)
_cell_length_c                   7.5897(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6478.3(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    35224
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2240
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans to fill the asymmetric unit'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2849
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2849
_reflns_number_gt                2185
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

All hydrogens were identified in the difference map and subsequently
placed in idealised positions and refined using a riding model.

An unidentified (probably Et2O) disordered solvent is present in channels
running along the c direction. This was treated using the Squeeze algorithm
(SQUEEZE - Sluis, P. v.d. & Spek, A. L. (1990) Acta Cryst. A46, 194-201.).
This has left a void of 252.00 A**3

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+39.3188P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1815
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002

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 0.72845(3) 0.78786(3) 0.00978(11) 0.0375(2) Uani 1 1 d . . .
N1 N 0.85227(8) 0.70208(9) -0.2097(3) 0.0268(6) Uani 1 1 d . . .
H1 H 0.8236 0.7068 -0.2408 0.032 Uiso 1 1 calc R . .
N2 N 0.80506(8) 0.74646(9) 0.1019(3) 0.0273(6) Uani 1 1 d . . .
H2A H 0.7873 0.7337 0.1817 0.033 Uiso 1 1 calc R . .
N3 N 0.81160(9) 0.79840(10) -0.1240(4) 0.0362(7) Uani 1 1 d . . .
H3A H 0.8412 0.7932 -0.1200 0.043 Uiso 1 1 calc R . .
C1 C 0.87118(10) 0.71272(10) -0.0482(4) 0.0228(7) Uani 1 1 d . . .
C2 C 0.88544(11) 0.68292(10) -0.3136(4) 0.0291(8) Uani 1 1 d . . .
H2 H 0.8809 0.6727 -0.4312 0.035 Uiso 1 1 calc R . .
C3 C 0.92561(10) 0.68052(10) -0.2251(4) 0.0257(7) Uani 1 1 d . . .
H3 H 0.9537 0.6688 -0.2692 0.031 Uiso 1 1 calc R . .
C4 C 0.91787(10) 0.69906(9) -0.0520(4) 0.0225(7) Uani 1 1 d . . .
C5 C 0.94444(10) 0.70365(10) 0.1007(4) 0.0239(7) Uani 1 1 d . . .
H5 H 0.9756 0.6945 0.1017 0.029 Uiso 1 1 calc R . .
C6 C 0.92426(10) 0.72172(10) 0.2496(4) 0.0258(7) Uani 1 1 d . . .
H6 H 0.9416 0.7241 0.3550 0.031 Uiso 1 1 calc R . .
C7 C 0.87888(10) 0.73659(10) 0.2485(4) 0.0245(7) Uani 1 1 d . . .
H7 H 0.8663 0.7497 0.3523 0.029 Uiso 1 1 calc R . .
C8 C 0.85203(9) 0.73269(10) 0.1003(4) 0.0218(7) Uani 1 1 d . . .
C9 C 0.78545(11) 0.77714(11) -0.0073(4) 0.0298(8) Uani 1 1 d . . .
C10 C 0.79470(13) 0.83011(14) -0.2599(5) 0.0488(10) Uani 1 1 d . . .
H10A H 0.7789 0.8126 -0.3535 0.059 Uiso 1 1 calc R . .
H10B H 0.7724 0.8516 -0.2069 0.059 Uiso 1 1 calc R . .
C11 C 0.83291(13) 0.85608(15) -0.3369(6) 0.0551(11) Uani 1 1 d . . .
H11A H 0.8568 0.8343 -0.3756 0.066 Uiso 1 1 calc R . .
H11B H 0.8465 0.8758 -0.2444 0.066 Uiso 1 1 calc R . .
C12 C 0.81941(13) 0.88615(14) -0.4936(5) 0.0494(11) Uani 1 1 d . . .
H12 H 0.7909 0.9032 -0.4619 0.059 Uiso 1 1 calc R . .
C13 C 0.81067(17) 0.86012(17) -0.6615(7) 0.0715(14) Uani 1 1 d . . .
H13A H 0.8034 0.8817 -0.7564 0.107 Uiso 1 1 calc R . .
H13B H 0.7849 0.8392 -0.6444 0.107 Uiso 1 1 calc R . .
H13C H 0.8380 0.8425 -0.6931 0.107 Uiso 1 1 calc R . .
C14 C 0.85758(16) 0.92071(16) -0.5203(7) 0.0671(14) Uani 1 1 d . . .
H14A H 0.8865 0.9045 -0.5401 0.101 Uiso 1 1 calc R . .
H14B H 0.8603 0.9400 -0.4152 0.101 Uiso 1 1 calc R . .
H14C H 0.8506 0.9399 -0.6228 0.101 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0222(4) 0.0663(6) 0.0238(4) 0.0061(4) 0.0021(3) 0.0124(4)
N1 0.0246(13) 0.0337(14) 0.0221(13) 0.0006(11) -0.0029(11) 0.0039(11)
N2 0.0184(12) 0.0387(15) 0.0247(14) 0.0071(12) 0.0052(11) 0.0027(11)
N3 0.0264(14) 0.0444(16) 0.0377(16) 0.0119(13) 0.0069(13) 0.0102(12)
C1 0.0270(15) 0.0229(15) 0.0185(15) 0.0038(12) 0.0001(12) -0.0019(12)
C2 0.0367(17) 0.0301(16) 0.0206(16) -0.0015(14) 0.0017(14) 0.0009(14)
C3 0.0248(15) 0.0235(15) 0.0289(17) 0.0018(13) 0.0044(13) 0.0049(12)
C4 0.0226(14) 0.0191(14) 0.0258(16) 0.0017(12) 0.0029(13) 0.0025(12)
C5 0.0186(14) 0.0243(15) 0.0288(16) 0.0037(13) -0.0018(13) 0.0020(12)
C6 0.0248(15) 0.0298(16) 0.0229(16) 0.0008(13) -0.0035(13) -0.0014(13)
C7 0.0273(15) 0.0254(15) 0.0208(15) 0.0021(13) 0.0031(13) -0.0009(12)
C8 0.0185(14) 0.0234(14) 0.0236(15) 0.0025(13) 0.0029(12) 0.0016(11)
C9 0.0283(16) 0.0380(18) 0.0230(16) -0.0016(14) 0.0004(14) 0.0052(14)
C10 0.044(2) 0.053(2) 0.049(2) 0.0216(19) 0.0079(18) 0.0174(17)
C11 0.046(2) 0.062(2) 0.057(3) 0.022(2) 0.011(2) 0.0158(19)
C12 0.047(2) 0.054(2) 0.048(2) 0.0174(19) 0.0118(19) 0.0141(18)
C13 0.077(3) 0.076(3) 0.062(3) 0.003(3) -0.011(3) -0.006(3)
C14 0.061(3) 0.071(3) 0.069(3) 0.004(3) 0.003(2) -0.004(2)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.699(3) . ?
N1 C2 1.369(4) . ?
N1 C1 1.380(4) . ?
N2 C9 1.349(4) . ?
N2 C8 1.430(4) . ?
N3 C9 1.324(4) . ?
N3 C10 1.472(5) . ?
C1 C8 1.387(4) . ?
C1 C4 1.422(4) . ?
C2 C3 1.354(4) . ?
C3 C4 1.439(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.395(4) . ?
C7 C8 1.376(4) . ?
C10 C11 1.471(5) . ?
C11 C12 1.530(5) . ?
C12 C13 1.506(6) . ?
C12 C14 1.518(6) . ?

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
C2 N1 C1 108.7(2) . . ?
C9 N2 C8 126.1(3) . . ?
C9 N3 C10 124.8(3) . . ?
N1 C1 C8 130.9(3) . . ?
N1 C1 C4 107.6(3) . . ?
C8 C1 C4 121.4(3) . . ?
C3 C2 N1 110.4(3) . . ?
C2 C3 C4 107.3(3) . . ?
C5 C4 C1 119.2(3) . . ?
C5 C4 C3 134.8(3) . . ?
C1 C4 C3 106.0(3) . . ?
C6 C5 C4 118.5(3) . . ?
C5 C6 C7 121.4(3) . . ?
C8 C7 C6 121.4(3) . . ?
C7 C8 C1 118.0(3) . . ?
C7 C8 N2 121.1(3) . . ?
C1 C8 N2 120.8(3) . . ?
N3 C9 N2 118.5(3) . . ?
N3 C9 S1 122.0(2) . . ?
N2 C9 S1 119.5(2) . . ?
C11 C10 N3 110.4(3) . . ?
C10 C11 C12 114.2(3) . . ?
C13 C12 C14 110.3(4) . . ?
C13 C12 C11 114.3(4) . . ?
C14 C12 C11 107.2(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.88 2.55 3.292(3) 142.3 13_664
N2 H2A S1 0.88 2.47 3.263(3) 150.5 13_665

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.070

_iucr_refine_instruction_details 
;
TITL 2010sot0813 in I4(1)/a
CELL 0.71073 29.2158 29.2158 7.5897 90.000 90.000 90.000
ZERR 16.00 0.0005 0.0005 0.0002 0.000 0.000 0.000
LATT 2
SYMM 1/2 - X, - Y, 1/2 + Z
SYMM 3/4 - Y, 1/4 + X, 1/4 + Z
SYMM 3/4 + Y, 3/4 - X, 3/4 + Z
SFAC C H N S
UNIT 224 304 48 16
MERG 2
SHEL 7 0.84
ACTA 55
TEMP -153
HTAB
SIZE 0.23 0.03 0.03
HTAB N1 S1_$1
EQIV $1 [ -x+3/2, -y+3/2, -z-1/2 ]
HTAB N2 S1_$2
EQIV $2[ -x+3/2, -y+3/2, -z+1/2 ]
DAMP 500
FMAP 2
PLAN 20
BOND
L.S. 4

WGHT 0.060900 39.318798
FVAR 1.00817
S1 4 0.728450 0.787861 0.009779 11.00000 0.02222 0.06633 =
0.02383 0.00607 0.00207 0.01236
N1 3 0.852268 0.702085 -0.209717 11.00000 0.02462 0.03373 =
0.02206 0.00061 -0.00291 0.00390
AFIX 43
H1 2 0.823640 0.706835 -0.240785 11.00000 -1.20000
AFIX 0
N2 3 0.805060 0.746458 0.101928 11.00000 0.01838 0.03869 =
0.02472 0.00710 0.00517 0.00266
AFIX 43
H2A 2 0.787287 0.733720 0.181670 11.00000 -1.20000
AFIX 0
N3 3 0.811600 0.798395 -0.124000 11.00000 0.02645 0.04442 =
0.03769 0.01194 0.00687 0.01024
AFIX 43
H3A 2 0.841246 0.793173 -0.120003 11.00000 -1.20000
AFIX 0

C1 1 0.871176 0.712721 -0.048204 11.00000 0.02704 0.02289 =
0.01847 0.00381 0.00013 -0.00192
C2 1 0.885437 0.682917 -0.313590 11.00000 0.03672 0.03010 =
0.02059 -0.00145 0.00165 0.00093
AFIX 43
H2 2 0.880903 0.672733 -0.431174 11.00000 -1.20000
AFIX 0
C3 1 0.925613 0.680519 -0.225146 11.00000 0.02483 0.02346 =
0.02890 0.00177 0.00441 0.00488
AFIX 43
H3 2 0.953695 0.668781 -0.269190 11.00000 -1.20000
AFIX 0
C4 1 0.917865 0.699059 -0.051998 11.00000 0.02259 0.01908 =
0.02583 0.00170 0.00293 0.00249
C5 1 0.944438 0.703652 0.100742 11.00000 0.01864 0.02430 =
0.02877 0.00365 -0.00177 0.00202
AFIX 43
H5 2 0.975647 0.694528 0.101718 11.00000 -1.20000
AFIX 0
C6 1 0.924260 0.721716 0.249598 11.00000 0.02481 0.02975 =
0.02287 0.00078 -0.00347 -0.00141
AFIX 43
H6 2 0.941621 0.724078 0.355041 11.00000 -1.20000
AFIX 0
C7 1 0.878880 0.736590 0.248530 11.00000 0.02732 0.02541 =
0.02082 0.00207 0.00309 -0.00091
AFIX 43
H7 2 0.866254 0.749683 0.352284 11.00000 -1.20000
AFIX 0
C8 1 0.852028 0.732689 0.100305 11.00000 0.01847 0.02342 =
0.02355 0.00247 0.00290 0.00159
C9 1 0.785448 0.777143 -0.007327 11.00000 0.02829 0.03802 =
0.02304 -0.00159 0.00041 0.00517
C10 1 0.794699 0.830114 -0.259870 11.00000 0.04429 0.05292 =
0.04928 0.02162 0.00791 0.01743
AFIX 23
H10A 2 0.778877 0.812630 -0.353549 11.00000 -1.20000
H10B 2 0.772374 0.851568 -0.206867 11.00000 -1.20000
AFIX 0
C11 1 0.832908 0.856082 -0.336912 11.00000 0.04643 0.06173 =
0.05719 0.02161 0.01085 0.01581
AFIX 23
H11A 2 0.856798 0.834256 -0.375630 11.00000 -1.20000
H11B 2 0.846450 0.875759 -0.244392 11.00000 -1.20000
AFIX 0
C12 1 0.819409 0.886153 -0.493599 11.00000 0.04665 0.05408 =
0.04750 0.01738 0.01181 0.01409
AFIX 13
H12 2 0.790881 0.903180 -0.461903 11.00000 -1.20000
AFIX 0
C13 1 0.810668 0.860123 -0.661532 11.00000 0.07676 0.07586 =
0.06180 0.00262 -0.01078 -0.00609
AFIX 137
H13A 2 0.803433 0.881704 -0.756375 11.00000 -1.50000
H13B 2 0.784850 0.839178 -0.644370 11.00000 -1.50000
H13C 2 0.838035 0.842549 -0.693129 11.00000 -1.50000
AFIX 0
C14 1 0.857578 0.920713 -0.520285 11.00000 0.06138 0.07054 =
0.06932 0.00407 0.00334 -0.00383
AFIX 137
H14A 2 0.886511 0.904538 -0.540058 11.00000 -1.50000
H14B 2 0.860261 0.940033 -0.415236 11.00000 -1.50000
H14C 2 0.850604 0.939882 -0.622789 11.00000 -1.50000

HKLF 4

REM 2010sot0813 in I4(1)/a
REM R1 = 0.0815 for 2185 Fo > 4sig(Fo) and 0.1060 for all 2849 data
REM 165 parameters refined using 0 restraints

END

WGHT 0.0607 39.3826
REM Highest difference peak 0.592, deepest hole -0.314, 1-sigma level 0.070
Q1 1 0.8148 0.8314 -0.4068 11.00000 0.05 0.59
Q2 1 0.8179 0.8502 -0.1819 11.00000 0.05 0.48
Q3 1 0.7417 0.8172 0.0537 11.00000 0.05 0.37
Q4 1 0.8319 0.8092 -0.0563 11.00000 0.05 0.32
Q5 1 0.8913 0.6621 -0.2656 11.00000 0.05 0.27
Q6 1 0.7011 0.7677 0.0743 11.00000 0.05 0.27
Q7 1 0.7068 0.7612 0.0994 11.00000 0.05 0.26
Q8 1 0.9257 0.6859 0.0461 11.00000 0.05 0.24
Q9 1 0.8908 0.7116 0.2992 11.00000 0.05 0.23
Q10 1 0.7386 0.9617 -0.3309 11.00000 0.05 0.23
Q11 1 0.7437 0.9922 -0.2526 11.00000 0.05 0.22
Q12 1 0.8912 0.7219 -0.0723 11.00000 0.05 0.22
Q13 1 0.9194 0.7013 0.1807 11.00000 0.05 0.22
Q14 1 0.8511 0.7262 -0.2301 11.00000 0.05 0.22
Q15 1 0.9000 0.8300 -0.3973 11.00000 0.05 0.21
Q16 1 0.8982 0.7211 0.2783 11.00000 0.05 0.21
Q17 1 0.8986 0.7570 0.2485 11.00000 0.05 0.21
Q18 1 0.8754 0.6784 -0.3984 11.00000 0.05 0.21
Q19 1 0.8301 0.7412 0.0919 11.00000 0.05 0.21
Q20 1 0.8546 0.7007 -0.1225 11.00000 0.05 0.21
;

#==END