# Electronic Supplementary Material (ESI) for Chemical Science
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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_2011sot0370
_database_code_depnum_ccdc_archive 'CCDC 879843'
#TrackingRef '- combined structures.cif'


_chemical_compound_source        'Stephen Moore'
_database_code_CSD               11ST0370
_database_code_depnum_ccdc_archive ?

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H49 Cl N4 S'
_chemical_formula_weight         545.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Pc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   10.0881(4)
_cell_length_b                   9.5939(2)
_cell_length_c                   17.0202(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.8840(10)
_cell_angle_gamma                90.00
_cell_volume                     1592.02(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11354
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Slab
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9357
_exptl_absorpt_correction_T_max  0.9916
_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  graphite
_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            17355
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5499
_reflns_number_gt                4989
_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.
;

_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^)+(0.0315P)^2^+0.2630P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(5)
_refine_ls_number_reflns         5499
_refine_ls_number_parameters     338
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.35607(6) 0.84241(7) 0.21776(4) 0.03195(16) Uani 1 1 d . . .
N1 N -0.1577(2) 0.7865(2) 0.23350(13) 0.0258(5) Uani 1 1 d . . .
H901 H -0.1284 0.7009 0.2460 0.031 Uiso 1 1 calc R . .
N2 N 0.14398(19) 0.79170(19) 0.28384(13) 0.0253(4) Uani 1 1 d . . .
H902 H 0.1126 0.7365 0.3163 0.030 Uiso 1 1 calc R . .
N3 N 0.28568(19) 0.61097(19) 0.28580(13) 0.0278(5) Uani 1 1 d . . .
H903 H 0.2241 0.5685 0.3057 0.033 Uiso 1 1 calc R . .
C1 C -0.2930(3) 0.8271(3) 0.20665(17) 0.0328(6) Uani 1 1 d . . .
H1 H -0.3699 0.7668 0.1992 0.039 Uiso 1 1 calc R . .
C2 C -0.2995(3) 0.9674(3) 0.19242(18) 0.0387(7) Uani 1 1 d . . .
H2 H -0.3808 1.0206 0.1731 0.046 Uiso 1 1 calc R . .
C3 C -0.1631(3) 1.0200(2) 0.21166(16) 0.0285(6) Uani 1 1 d . . .
C4 C -0.1021(3) 1.1522(3) 0.21200(17) 0.0355(7) Uani 1 1 d . . .
H4 H -0.1573 1.2328 0.1966 0.043 Uiso 1 1 calc R . .
C5 C 0.0376(3) 1.1630(3) 0.23476(16) 0.0355(7) Uani 1 1 d . . .
H5 H 0.0781 1.2523 0.2345 0.043 Uiso 1 1 calc R . .
C6 C 0.1232(3) 1.0475(2) 0.25847(15) 0.0297(6) Uani 1 1 d . . .
H6 H 0.2199 1.0595 0.2738 0.036 Uiso 1 1 calc R . .
C7 C 0.0672(2) 0.9152(2) 0.25960(14) 0.0239(5) Uani 1 1 d . . .
C8 C -0.0757(2) 0.9037(2) 0.23751(14) 0.0225(5) Uani 1 1 d . . .
C9 C 0.2596(2) 0.7460(2) 0.26416(15) 0.0236(5) Uani 1 1 d . . .
C10 C 0.4005(2) 0.5296(3) 0.28019(15) 0.0266(5) Uani 1 1 d . . .
C11 C 0.5342(2) 0.5769(3) 0.31060(17) 0.0338(6) Uani 1 1 d . . .
H11 H 0.5511 0.6679 0.3330 0.041 Uiso 1 1 calc R . .
C12 C 0.6423(3) 0.4897(3) 0.30777(18) 0.0419(8) Uani 1 1 d . . .
H12 H 0.7339 0.5223 0.3270 0.050 Uiso 1 1 calc R . .
C13 C 0.6188(3) 0.3560(4) 0.27740(18) 0.0493(9) Uani 1 1 d . . .
H13 H 0.6938 0.2970 0.2760 0.059 Uiso 1 1 calc R . .
C14 C 0.4856(3) 0.3084(3) 0.24905(19) 0.0495(8) Uani 1 1 d . . .
H14 H 0.4688 0.2160 0.2288 0.059 Uiso 1 1 calc R . .
C15 C 0.3769(3) 0.3955(3) 0.25020(17) 0.0362(6) Uani 1 1 d . . .
H15 H 0.2855 0.3630 0.2302 0.043 Uiso 1 1 calc R . .
N4 N -0.00127(19) 0.86684(19) -0.00599(11) 0.0212(4) Uani 1 1 d . . .
C16 C -0.1344(2) 0.9138(2) -0.06577(14) 0.0238(5) Uani 1 1 d . . .
H16A H -0.1117 0.9845 -0.1026 0.029 Uiso 1 1 calc R . .
H16B H -0.1751 0.8328 -0.0994 0.029 Uiso 1 1 calc R . .
C17 C -0.2414(2) 0.9746(2) -0.02719(16) 0.0293(6) Uani 1 1 d . . .
H17A H -0.2049 1.0608 0.0026 0.035 Uiso 1 1 calc R . .
H17B H -0.2607 0.9072 0.0125 0.035 Uiso 1 1 calc R . .
C18 C -0.3741(3) 1.0081(3) -0.09047(18) 0.0365(6) Uani 1 1 d . . .
H18A H -0.4123 0.9213 -0.1189 0.044 Uiso 1 1 calc R . .
H18B H -0.3542 1.0728 -0.1313 0.044 Uiso 1 1 calc R . .
C19 C -0.4801(3) 1.0742(3) -0.05213(19) 0.0388(7) Uani 1 1 d . . .
H19A H -0.4977 1.0117 -0.0104 0.058 Uiso 1 1 calc R . .
H19B H -0.5656 1.0898 -0.0941 0.058 Uiso 1 1 calc R . .
H19C H -0.4452 1.1634 -0.0273 0.058 Uiso 1 1 calc R . .
C20 C 0.0669(2) 0.9898(2) 0.04604(15) 0.0233(5) Uani 1 1 d . . .
H20A H 0.0013 1.0282 0.0748 0.028 Uiso 1 1 calc R . .
H20B H 0.1473 0.9546 0.0878 0.028 Uiso 1 1 calc R . .
C21 C 0.1141(2) 1.1078(2) -0.00028(15) 0.0262(5) Uani 1 1 d . . .
H21A H 0.0340 1.1500 -0.0392 0.031 Uiso 1 1 calc R . .
H21B H 0.1771 1.0710 -0.0313 0.031 Uiso 1 1 calc R . .
C22 C 0.1877(3) 1.2181(3) 0.06050(17) 0.0352(6) Uani 1 1 d . . .
H22A H 0.1227 1.2566 0.0897 0.042 Uiso 1 1 calc R . .
H22B H 0.2639 1.1734 0.1012 0.042 Uiso 1 1 calc R . .
C23 C 0.2448(3) 1.3371(3) 0.01913(19) 0.0408(7) Uani 1 1 d . . .
H23A H 0.3087 1.2993 -0.0102 0.061 Uiso 1 1 calc R . .
H23B H 0.2932 1.4035 0.0603 0.061 Uiso 1 1 calc R . .
H23C H 0.1692 1.3846 -0.0192 0.061 Uiso 1 1 calc R . .
C24 C 0.0916(2) 0.8088(2) -0.05600(15) 0.0257(5) Uani 1 1 d . . .
H24A H 0.0449 0.7287 -0.0881 0.031 Uiso 1 1 calc R . .
H24B H 0.1042 0.8813 -0.0948 0.031 Uiso 1 1 calc R . .
C25 C 0.2322(2) 0.7615(3) -0.00637(16) 0.0309(6) Uani 1 1 d . . .
H25A H 0.2216 0.6835 0.0296 0.037 Uiso 1 1 calc R . .
H25B H 0.2785 0.8393 0.0282 0.037 Uiso 1 1 calc R . .
C26 C 0.3196(3) 0.7145(3) -0.06285(18) 0.0362(6) Uani 1 1 d . . .
H26A H 0.2718 0.6378 -0.0978 0.043 Uiso 1 1 calc R . .
H26B H 0.3292 0.7931 -0.0987 0.043 Uiso 1 1 calc R . .
C27 C 0.4613(3) 0.6652(3) -0.0171(2) 0.0424(7) Uani 1 1 d . . .
H27A H 0.5098 0.7410 0.0170 0.064 Uiso 1 1 calc R . .
H27B H 0.5129 0.6370 -0.0560 0.064 Uiso 1 1 calc R . .
H27C H 0.4526 0.5855 0.0173 0.064 Uiso 1 1 calc R . .
C28 C -0.0303(2) 0.7574(2) 0.05195(14) 0.0240(5) Uani 1 1 d . . .
H28A H -0.0855 0.8007 0.0858 0.029 Uiso 1 1 calc R . .
H28B H 0.0579 0.7274 0.0887 0.029 Uiso 1 1 calc R . .
C29 C -0.1061(3) 0.6289(2) 0.01041(16) 0.0286(6) Uani 1 1 d . . .
H29A H -0.1993 0.6563 -0.0209 0.034 Uiso 1 1 calc R . .
H29B H -0.0569 0.5911 -0.0283 0.034 Uiso 1 1 calc R . .
C30 C -0.1173(4) 0.5173(3) 0.0702(2) 0.0610(10) Uani 1 1 d . . .
H30A H -0.1673 0.5546 0.1087 0.073 Uiso 1 1 calc R . .
H30B H -0.0242 0.4901 0.1019 0.073 Uiso 1 1 calc R . .
C31 C -0.1924(4) 0.3890(3) 0.0275(2) 0.0642(11) Uani 1 1 d . . .
H31A H -0.2873 0.4139 0.0002 0.096 Uiso 1 1 calc R . .
H31B H -0.1921 0.3157 0.0676 0.096 Uiso 1 1 calc R . .
H31C H -0.1460 0.3551 -0.0129 0.096 Uiso 1 1 calc R . .
Cl1 Cl 0.00116(5) 0.51087(5) 0.31853(4) 0.02890(15) 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
S1 0.0220(3) 0.0416(4) 0.0324(4) 0.0135(3) 0.0072(3) -0.0001(3)
N1 0.0235(10) 0.0263(10) 0.0291(13) 0.0032(9) 0.0095(9) 0.0036(8)
N2 0.0243(11) 0.0251(10) 0.0289(12) 0.0066(9) 0.0111(9) 0.0007(8)
N3 0.0183(11) 0.0277(11) 0.0391(14) 0.0032(9) 0.0105(10) 0.0012(8)
C1 0.0223(13) 0.0487(16) 0.0282(15) 0.0069(12) 0.0082(12) 0.0040(11)
C2 0.0352(15) 0.0513(17) 0.0341(16) 0.0145(13) 0.0171(13) 0.0207(12)
C3 0.0342(15) 0.0332(13) 0.0218(14) 0.0046(11) 0.0141(12) 0.0128(11)
C4 0.057(2) 0.0294(14) 0.0270(15) 0.0070(11) 0.0241(14) 0.0164(12)
C5 0.0607(19) 0.0252(13) 0.0260(16) 0.0014(11) 0.0211(14) -0.0018(12)
C6 0.0428(15) 0.0286(13) 0.0199(14) -0.0022(11) 0.0120(12) -0.0028(11)
C7 0.0287(13) 0.0269(12) 0.0164(13) -0.0027(10) 0.0063(11) 0.0016(10)
C8 0.0291(13) 0.0243(12) 0.0170(13) 0.0017(9) 0.0110(11) 0.0044(9)
C9 0.0181(12) 0.0302(13) 0.0211(14) -0.0003(10) 0.0024(10) -0.0031(9)
C10 0.0196(12) 0.0374(14) 0.0244(14) 0.0060(11) 0.0083(11) 0.0039(10)
C11 0.0237(14) 0.0415(15) 0.0362(16) 0.0140(12) 0.0076(12) -0.0009(10)
C12 0.0185(13) 0.068(2) 0.0407(18) 0.0252(15) 0.0099(13) 0.0103(12)
C13 0.0396(18) 0.080(2) 0.0321(18) 0.0150(16) 0.0167(14) 0.0352(16)
C14 0.054(2) 0.0560(18) 0.0365(18) -0.0106(14) 0.0076(15) 0.0239(15)
C15 0.0298(14) 0.0441(16) 0.0308(16) -0.0058(12) 0.0009(12) 0.0061(11)
N4 0.0262(11) 0.0233(10) 0.0139(10) -0.0035(8) 0.0050(8) -0.0004(8)
C16 0.0271(13) 0.0268(12) 0.0149(13) 0.0021(10) 0.0008(10) -0.0021(9)
C17 0.0278(13) 0.0307(13) 0.0290(15) -0.0004(11) 0.0067(11) -0.0007(10)
C18 0.0319(15) 0.0410(15) 0.0326(16) 0.0001(12) 0.0013(12) 0.0072(11)
C19 0.0269(14) 0.0394(15) 0.0481(19) 0.0022(13) 0.0060(13) 0.0078(11)
C20 0.0288(13) 0.0211(12) 0.0205(13) -0.0052(9) 0.0072(11) -0.0030(9)
C21 0.0297(14) 0.0276(13) 0.0212(14) -0.0024(10) 0.0064(11) -0.0024(10)
C22 0.0400(16) 0.0327(15) 0.0287(16) 0.0008(11) 0.0014(12) -0.0096(11)
C23 0.0497(18) 0.0321(15) 0.0389(18) -0.0020(12) 0.0085(14) -0.0126(12)
C24 0.0292(13) 0.0281(12) 0.0227(14) -0.0065(10) 0.0120(11) -0.0016(10)
C25 0.0322(14) 0.0314(13) 0.0310(16) -0.0016(11) 0.0118(12) 0.0038(10)
C26 0.0261(14) 0.0447(16) 0.0394(18) -0.0136(13) 0.0111(13) -0.0032(11)
C27 0.0352(16) 0.0377(16) 0.057(2) -0.0020(14) 0.0158(15) 0.0024(11)
C28 0.0318(13) 0.0235(11) 0.0167(13) 0.0028(9) 0.0064(11) -0.0001(9)
C29 0.0318(14) 0.0254(12) 0.0270(15) -0.0001(10) 0.0048(12) -0.0026(10)
C30 0.106(3) 0.0324(16) 0.0324(18) 0.0076(13) -0.0047(19) -0.0249(16)
C31 0.107(3) 0.0335(16) 0.038(2) 0.0092(14) -0.007(2) -0.0276(17)
Cl1 0.0222(3) 0.0256(3) 0.0399(4) 0.0069(3) 0.0098(3) 0.0009(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 1.680(2) . ?
N1 C1 1.379(3) . ?
N1 C8 1.387(3) . ?
N2 C9 1.365(3) . ?
N2 C7 1.418(3) . ?
N3 C9 1.354(3) . ?
N3 C10 1.420(3) . ?
C1 C2 1.367(4) . ?
C2 C3 1.422(4) . ?
C3 C4 1.410(4) . ?
C3 C8 1.421(3) . ?
C4 C5 1.365(4) . ?
C5 C6 1.399(4) . ?
C6 C7 1.392(3) . ?
C7 C8 1.397(3) . ?
C10 C15 1.382(4) . ?
C10 C11 1.391(3) . ?
C11 C12 1.386(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.384(5) . ?
C14 C15 1.383(4) . ?
N4 C28 1.519(3) . ?
N4 C24 1.524(3) . ?
N4 C20 1.528(3) . ?
N4 C16 1.530(3) . ?
C16 C17 1.517(3) . ?
C17 C18 1.521(4) . ?
C18 C19 1.527(4) . ?
C20 C21 1.524(3) . ?
C21 C22 1.532(3) . ?
C22 C23 1.530(4) . ?
C24 C25 1.521(3) . ?
C25 C26 1.530(3) . ?
C26 C27 1.517(4) . ?
C28 C29 1.526(3) . ?
C29 C30 1.501(4) . ?
C30 C31 1.529(4) . ?

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
C1 N1 C8 108.33(19) . . ?
C9 N2 C7 129.4(2) . . ?
C9 N3 C10 127.79(19) . . ?
C2 C1 N1 109.6(2) . . ?
C1 C2 C3 108.0(2) . . ?
C4 C3 C8 118.0(2) . . ?
C4 C3 C2 135.7(2) . . ?
C8 C3 C2 106.3(2) . . ?
C5 C4 C3 119.2(2) . . ?
C4 C5 C6 122.5(2) . . ?
C7 C6 C5 120.2(3) . . ?
C6 C7 C8 117.6(2) . . ?
C6 C7 N2 124.9(2) . . ?
C8 C7 N2 117.47(19) . . ?
N1 C8 C7 129.7(2) . . ?
N1 C8 C3 107.8(2) . . ?
C7 C8 C3 122.5(2) . . ?
N3 C9 N2 111.04(19) . . ?
N3 C9 S1 123.97(17) . . ?
N2 C9 S1 124.98(18) . . ?
C15 C10 C11 120.0(2) . . ?
C15 C10 N3 118.1(2) . . ?
C11 C10 N3 121.7(2) . . ?
C12 C11 C10 119.1(3) . . ?
C13 C12 C11 120.9(3) . . ?
C12 C13 C14 119.7(2) . . ?
C15 C14 C13 119.8(3) . . ?
C10 C15 C14 120.5(3) . . ?
C28 N4 C24 111.03(17) . . ?
C28 N4 C20 106.86(17) . . ?
C24 N4 C20 110.87(17) . . ?
C28 N4 C16 110.63(17) . . ?
C24 N4 C16 107.27(18) . . ?
C20 N4 C16 110.22(17) . . ?
C17 C16 N4 115.23(19) . . ?
C16 C17 C18 111.7(2) . . ?
C17 C18 C19 111.8(2) . . ?
C21 C20 N4 115.3(2) . . ?
C20 C21 C22 109.0(2) . . ?
C23 C22 C21 112.3(2) . . ?
C25 C24 N4 114.7(2) . . ?
C24 C25 C26 110.1(2) . . ?
C27 C26 C25 112.9(2) . . ?
N4 C28 C29 114.50(19) . . ?
C30 C29 C28 112.2(2) . . ?
C29 C30 C31 111.5(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
N1 H901 Cl1 0.88 2.39 3.235(2) 160.1 .
N2 H902 Cl1 0.88 2.44 3.1813(19) 141.6 .
N3 H903 Cl1 0.88 2.38 3.208(2) 156.9 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037

_iucr_refine_instruction_details 
;
TITL 2011sot0370 in Pc
CELL 0.71073 10.0881 9.5939 17.0202 90.000 104.884 90.000
ZERR 2.00 0.0004 0.0002 0.0007 0.000 0.001 0.000
LATT -1
SYMM X, - Y, 1/2 + Z
SFAC C H N S CL
UNIT 62 98 8 2 2
MERG 2
SHEL 7 0.84
OMIT 0 0 -4
OMIT 0 0 4
OMIT 1 1 -1
FMAP 2
PLAN 10
SIZE 0.04 0.24 0.32
ACTA 55.00
HTAB
HTAB N1 CL1
HTAB N2 CL1
HTAB N3 CL1
BOND
L.S. 4
TEMP -153.00
WGHT 0.031500 0.263000
FVAR 0.23475
MOLE 1
S1 4 0.356069 0.842415 0.217758 11.00000 0.02201 0.04158 =
0.03240 0.01350 0.00723 -0.00011
N1 3 -0.157704 0.786498 0.233500 11.00000 0.02348 0.02635 =
0.02906 0.00318 0.00953 0.00357
AFIX 43
H901 2 -0.128450 0.700894 0.245955 11.00000 -1.20000
AFIX 0
N2 3 0.143979 0.791701 0.283836 11.00000 0.02428 0.02507 =
0.02892 0.00659 0.01106 0.00070
AFIX 43
H902 2 0.112642 0.736506 0.316254 11.00000 -1.20000
AFIX 0
N3 3 0.285677 0.610966 0.285801 11.00000 0.01829 0.02768 =
0.03905 0.00316 0.01055 0.00125
AFIX 43
H903 2 0.224126 0.568550 0.305729 11.00000 -1.20000
AFIX 0
C1 1 -0.292984 0.827108 0.206655 11.00000 0.02228 0.04873 =
0.02823 0.00688 0.00817 0.00400
AFIX 43
H1 2 -0.369878 0.766758 0.199201 11.00000 -1.20000
AFIX 0
C2 1 -0.299463 0.967449 0.192421 11.00000 0.03524 0.05127 =
0.03413 0.01449 0.01715 0.02066
AFIX 43
H2 2 -0.380786 1.020574 0.173067 11.00000 -1.20000
AFIX 0
C3 1 -0.163139 1.019992 0.211661 11.00000 0.03422 0.03322 =
0.02176 0.00457 0.01409 0.01282
C4 1 -0.102056 1.152205 0.211996 11.00000 0.05744 0.02935 =
0.02696 0.00703 0.02409 0.01635
AFIX 43
H4 2 -0.157327 1.232802 0.196576 11.00000 -1.20000
AFIX 0
C5 1 0.037564 1.162959 0.234765 11.00000 0.06069 0.02518 =
0.02603 0.00136 0.02108 -0.00185
AFIX 43
H5 2 0.078097 1.252279 0.234496 11.00000 -1.20000
AFIX 0
C6 1 0.123219 1.047545 0.258469 11.00000 0.04276 0.02862 =
0.01990 -0.00223 0.01199 -0.00284
AFIX 43
H6 2 0.219937 1.059512 0.273846 11.00000 -1.20000
AFIX 0
C7 1 0.067160 0.915159 0.259600 11.00000 0.02874 0.02690 =
0.01636 -0.00270 0.00633 0.00158
C8 1 -0.075660 0.903651 0.237509 11.00000 0.02913 0.02432 =
0.01698 0.00165 0.01100 0.00435
C9 1 0.259559 0.746035 0.264157 11.00000 0.01809 0.03025 =
0.02109 -0.00031 0.00239 -0.00311
C10 1 0.400457 0.529599 0.280194 11.00000 0.01960 0.03744 =
0.02438 0.00597 0.00835 0.00388
C11 1 0.534180 0.576932 0.310597 11.00000 0.02366 0.04155 =
0.03617 0.01403 0.00759 -0.00089
AFIX 43
H11 2 0.551143 0.667879 0.333002 11.00000 -1.20000
AFIX 0
C12 1 0.642328 0.489658 0.307768 11.00000 0.01846 0.06765 =
0.04071 0.02523 0.00990 0.01034
AFIX 43
H12 2 0.733867 0.522271 0.326991 11.00000 -1.20000
AFIX 0
C13 1 0.618818 0.356002 0.277397 11.00000 0.03959 0.08026 =
0.03215 0.01503 0.01668 0.03517
AFIX 43
H13 2 0.693763 0.296967 0.275959 11.00000 -1.20000
AFIX 0
C14 1 0.485573 0.308362 0.249045 11.00000 0.05376 0.05598 =
0.03653 -0.01060 0.00763 0.02391
AFIX 43
H14 2 0.468788 0.215986 0.228835 11.00000 -1.20000
AFIX 0
C15 1 0.376948 0.395515 0.250203 11.00000 0.02984 0.04408 =
0.03075 -0.00580 0.00088 0.00609
AFIX 43
H15 2 0.285518 0.362996 0.230242 11.00000 -1.20000
AFIX 0
MOLE 2
N4 3 -0.001268 0.866841 -0.005991 11.00000 0.02624 0.02325 =
0.01391 -0.00352 0.00498 -0.00041
C16 1 -0.134403 0.913797 -0.065771 11.00000 0.02713 0.02676 =
0.01489 0.00205 0.00082 -0.00207
AFIX 23
H16A 2 -0.111694 0.984519 -0.102624 11.00000 -1.20000
H16B 2 -0.175136 0.832792 -0.099431 11.00000 -1.20000
AFIX 0
C17 1 -0.241433 0.974642 -0.027193 11.00000 0.02775 0.03069 =
0.02898 -0.00044 0.00666 -0.00073
AFIX 23
H17A 2 -0.204921 1.060812 0.002586 11.00000 -1.20000
H17B 2 -0.260661 0.907248 0.012527 11.00000 -1.20000
AFIX 0
C18 1 -0.374067 1.008090 -0.090467 11.00000 0.03189 0.04097 =
0.03264 0.00013 0.00128 0.00715
AFIX 23
H18A 2 -0.412311 0.921300 -0.118873 11.00000 -1.20000
H18B 2 -0.354249 1.072785 -0.131320 11.00000 -1.20000
AFIX 0
C19 1 -0.480126 1.074167 -0.052128 11.00000 0.02688 0.03938 =
0.04813 0.00221 0.00599 0.00781
AFIX 137
H19A 2 -0.497702 1.011715 -0.010366 11.00000 -1.50000
H19B 2 -0.565598 1.089756 -0.094140 11.00000 -1.50000
H19C 2 -0.445156 1.163444 -0.027269 11.00000 -1.50000
AFIX 0
C20 1 0.066863 0.989766 0.046041 11.00000 0.02882 0.02105 =
0.02046 -0.00524 0.00723 -0.00296
AFIX 23
H20A 2 0.001324 1.028232 0.074841 11.00000 -1.20000
H20B 2 0.147288 0.954615 0.087753 11.00000 -1.20000
AFIX 0
C21 1 0.114085 1.107761 -0.000284 11.00000 0.02968 0.02759 =
0.02115 -0.00237 0.00638 -0.00242
AFIX 23
H21A 2 0.034024 1.149956 -0.039200 11.00000 -1.20000
H21B 2 0.177089 1.070981 -0.031323 11.00000 -1.20000
AFIX 0
C22 1 0.187726 1.218061 0.060501 11.00000 0.03996 0.03271 =
0.02875 0.00078 0.00142 -0.00961
AFIX 23
H22A 2 0.122739 1.256627 0.089657 11.00000 -1.20000
H22B 2 0.263945 1.173415 0.101153 11.00000 -1.20000
AFIX 0
C23 1 0.244833 1.337080 0.019128 11.00000 0.04975 0.03209 =
0.03895 -0.00203 0.00853 -0.01256
AFIX 137
H23A 2 0.308651 1.299345 -0.010226 11.00000 -1.50000
H23B 2 0.293222 1.403513 0.060330 11.00000 -1.50000
H23C 2 0.169210 1.384633 -0.019224 11.00000 -1.50000
AFIX 0
C24 1 0.091605 0.808798 -0.056000 11.00000 0.02920 0.02807 =
0.02272 -0.00655 0.01199 -0.00158
AFIX 23
H24A 2 0.044894 0.728652 -0.088140 11.00000 -1.20000
H24B 2 0.104223 0.881328 -0.094816 11.00000 -1.20000
AFIX 0
C25 1 0.232161 0.761534 -0.006366 11.00000 0.03217 0.03138 =
0.03104 -0.00158 0.01176 0.00377
AFIX 23
H25A 2 0.221623 0.683453 0.029576 11.00000 -1.20000
H25B 2 0.278469 0.839269 0.028247 11.00000 -1.20000
AFIX 0
C26 1 0.319577 0.714524 -0.062850 11.00000 0.02609 0.04472 =
0.03942 -0.01356 0.01114 -0.00319
AFIX 23
H26A 2 0.271755 0.637844 -0.097784 11.00000 -1.20000
H26B 2 0.329157 0.793116 -0.098683 11.00000 -1.20000
AFIX 0
C27 1 0.461265 0.665156 -0.017091 11.00000 0.03521 0.03773 =
0.05657 -0.00201 0.01581 0.00240
AFIX 137
H27A 2 0.509776 0.741044 0.017002 11.00000 -1.50000
H27B 2 0.512921 0.637042 -0.056009 11.00000 -1.50000
H27C 2 0.452616 0.585493 0.017291 11.00000 -1.50000
AFIX 0
C28 1 -0.030318 0.757447 0.051952 11.00000 0.03182 0.02347 =
0.01667 0.00283 0.00640 -0.00014
AFIX 23
H28A 2 -0.085491 0.800736 0.085850 11.00000 -1.20000
H28B 2 0.057868 0.727416 0.088724 11.00000 -1.20000
AFIX 0
C29 1 -0.106068 0.628901 0.010412 11.00000 0.03179 0.02535 =
0.02699 -0.00014 0.00476 -0.00261
AFIX 23
H29A 2 -0.199266 0.656321 -0.020932 11.00000 -1.20000
H29B 2 -0.056950 0.591072 -0.028337 11.00000 -1.20000
AFIX 0
C30 1 -0.117291 0.517336 0.070234 11.00000 0.10571 0.03243 =
0.03239 0.00763 -0.00470 -0.02493
AFIX 23
H30A 2 -0.167293 0.554570 0.108691 11.00000 -1.20000
H30B 2 -0.024230 0.490077 0.101880 11.00000 -1.20000
AFIX 0
C31 1 -0.192397 0.389004 0.027462 11.00000 0.10668 0.03346 =
0.03840 0.00917 -0.00703 -0.02756
AFIX 137
H31A 2 -0.287273 0.413926 0.000199 11.00000 -1.50000
H31B 2 -0.192055 0.315704 0.067616 11.00000 -1.50000
H31C 2 -0.146014 0.355106 -0.012850 11.00000 -1.50000
AFIX 0
MOLE 3
CL1 5 0.001162 0.510868 0.318532 11.00000 0.02222 0.02556 =
0.03991 0.00694 0.00980 0.00086
HKLF 4

REM 2011sot0370 in Pc
REM R1 = 0.0374 for 4989 Fo > 4sig(Fo) and 0.0443 for all 5499 data
REM 338 parameters refined using 2 restraints

END

WGHT 0.0266 0.3169
REM Highest difference peak 0.165, deepest hole -0.174, 1-sigma level 0.037
Q1 1 0.6858 0.2153 0.2701 11.00000 0.05 0.17
Q2 1 -0.0786 0.5297 0.1318 11.00000 0.05 0.15
Q3 1 -0.3830 0.6878 0.1977 11.00000 0.05 0.15
Q4 1 0.1014 0.6620 0.2097 11.00000 0.05 0.14
Q5 1 0.0637 0.7043 0.2960 11.00000 0.05 0.14
Q6 1 0.8258 0.3625 0.2604 11.00000 0.05 0.14
Q7 1 0.4725 0.8638 -0.0267 11.00000 0.05 0.13
Q8 1 0.0004 0.9079 0.2551 11.00000 0.05 0.13
Q9 1 0.5380 0.6282 -0.0757 11.00000 0.05 0.13
Q10 1 0.7557 0.6571 0.2977 11.00000 0.05 0.13
;


data_2011sot0549
_database_code_depnum_ccdc_archive 'CCDC 879844'
#TrackingRef '- combined structures.cif'


_chemical_compound_source        'Stephen Moore'
_database_code_CSD               1SOT0549

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 F3 N3 O, C16 H36 N, Cl'
_chemical_formula_sum            'C36 H64 Cl F3 N4 O'
_chemical_formula_weight         661.36

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
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                   17.0415(6)
_cell_length_b                   14.5286(8)
_cell_length_c                   17.7209(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.023(2)
_cell_angle_gamma                90.00
_cell_volume                     3942.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    39359
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.37

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9972
_exptl_absorpt_process_details   
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;

_exptl_special_details           
;
SADABS was used to perform the Absorption correction
Parameter refinement on 19753 reflections reduced R(int) from 0.1955 to 0.0846
Ratio of minimum to maximum apparent transmission: 0.699270
The given Tmin and Tmax were generated using the SHELX SIZE command
;

_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            31420
_diffrn_reflns_av_R_equivalents  0.1506
_diffrn_reflns_av_sigmaI/netI    0.1326
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6931
_reflns_number_gt                3943
_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    'CAMERON (Watkin, et al., 1993)'
_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.
;

_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^+16.1552P] 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         6931
_refine_ls_number_parameters     412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2056
_refine_ls_R_factor_gt           0.1167
_refine_ls_wR_factor_ref         0.2232
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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 0.16806(9) 0.69259(11) 0.57160(9) 0.0322(4) Uani 1 1 d . . .
F1 F 0.1815(2) 0.2627(3) 0.2825(2) 0.0462(10) Uani 1 1 d . . .
F2 F 0.3119(3) 0.2208(3) 0.3576(3) 0.0664(14) Uani 1 1 d . . .
F3 F 0.2851(3) 0.3219(3) 0.2633(3) 0.0694(14) Uani 1 1 d . . .
O1 O 0.0180(2) 0.4696(3) 0.3329(2) 0.0293(10) Uani 1 1 d . . .
N1 N 0.3198(3) 0.5792(3) 0.5524(3) 0.0300(12) Uani 1 1 d . . .
H1 H 0.2853 0.6167 0.5630 0.036 Uiso 1 1 calc R . .
N2 N 0.1388(3) 0.5340(3) 0.4416(3) 0.0283(12) Uani 1 1 d . . .
H2 H 0.1540 0.5776 0.4798 0.034 Uiso 1 1 calc R . .
N3 N 0.0006(3) 0.5763(3) 0.4177(3) 0.0304(12) Uani 1 1 d . . .
H3 H 0.0269 0.6159 0.4588 0.036 Uiso 1 1 calc R . .
C1 C 0.4373(7) 0.8914(7) 0.5652(7) 0.104(4) Uani 1 1 d . . .
H1A H 0.3761 0.9060 0.5501 0.157 Uiso 1 1 calc R . .
H1B H 0.4523 0.9127 0.5207 0.157 Uiso 1 1 calc R . .
H1C H 0.4749 0.9221 0.6180 0.157 Uiso 1 1 calc R . .
C2 C 0.4512(5) 0.7845(6) 0.5761(5) 0.068(2) Uani 1 1 d . . .
H2A H 0.4139 0.7543 0.5220 0.081 Uiso 1 1 calc R . .
H2B H 0.5128 0.7704 0.5895 0.081 Uiso 1 1 calc R . .
C3 C 0.4307(5) 0.7445(6) 0.6429(5) 0.061(2) Uani 1 1 d . . .
H3A H 0.3670 0.7486 0.6247 0.074 Uiso 1 1 calc R . .
H3B H 0.4600 0.7817 0.6946 0.074 Uiso 1 1 calc R . .
C4 C 0.4586(4) 0.6463(5) 0.6628(4) 0.0439(18) Uani 1 1 d . . .
H4A H 0.4507 0.6275 0.7128 0.053 Uiso 1 1 calc R . .
H4B H 0.5216 0.6419 0.6776 0.053 Uiso 1 1 calc R . .
C5 C 0.4100(4) 0.5797(4) 0.5928(4) 0.0307(15) Uani 1 1 d . . .
C6 C 0.4409(4) 0.5113(4) 0.5597(3) 0.0298(14) Uani 1 1 d . . .
H6 H 0.5005 0.4966 0.5762 0.036 Uiso 1 1 calc R . .
C7 C 0.3673(3) 0.4662(4) 0.4962(3) 0.0249(13) Uani 1 1 d . . .
C8 C 0.3570(4) 0.3935(4) 0.4407(4) 0.0267(14) Uani 1 1 d . . .
H8 H 0.4062 0.3621 0.4415 0.032 Uiso 1 1 calc R . .
C9 C 0.2733(3) 0.3689(4) 0.3849(3) 0.0242(13) Uani 1 1 d . . .
C10 C 0.1984(3) 0.4131(4) 0.3817(3) 0.0221(13) Uani 1 1 d . . .
H10 H 0.1420 0.3939 0.3421 0.027 Uiso 1 1 calc R . .
C11 C 0.2073(3) 0.4851(4) 0.4368(3) 0.0240(13) Uani 1 1 d . . .
C12 C 0.2929(3) 0.5109(4) 0.4929(3) 0.0258(13) Uani 1 1 d . . .
C13 C 0.2633(4) 0.2950(4) 0.3237(4) 0.0291(14) Uani 1 1 d . . .
C14 C 0.0495(3) 0.5219(4) 0.3930(3) 0.0243(13) Uani 1 1 d . . .
C15 C -0.0942(3) 0.5710(4) 0.3781(4) 0.0269(14) Uani 1 1 d . . .
H15A H -0.1126 0.5089 0.3871 0.032 Uiso 1 1 calc R . .
H15B H -0.1167 0.5808 0.3169 0.032 Uiso 1 1 calc R . .
C16 C -0.1325(3) 0.6428(4) 0.4142(4) 0.0280(14) Uani 1 1 d . . .
H16A H -0.1127 0.7045 0.4063 0.034 Uiso 1 1 calc R . .
H16B H -0.1106 0.6321 0.4753 0.034 Uiso 1 1 calc R . .
C17 C -0.2323(3) 0.6404(4) 0.3728(4) 0.0264(13) Uani 1 1 d . . .
H17A H -0.2540 0.6481 0.3114 0.032 Uiso 1 1 calc R . .
H17B H -0.2519 0.5795 0.3829 0.032 Uiso 1 1 calc R . .
C18 C -0.2723(4) 0.7148(4) 0.4054(4) 0.0344(15) Uani 1 1 d . . .
H18A H -0.2542 0.7043 0.4660 0.041 Uiso 1 1 calc R . .
H18B H -0.2491 0.7754 0.3994 0.041 Uiso 1 1 calc R . .
C19 C -0.3711(4) 0.7173(5) 0.3600(4) 0.0467(19) Uani 1 1 d . . .
H19A H -0.3943 0.6568 0.3662 0.056 Uiso 1 1 calc R . .
H19B H -0.3892 0.7276 0.2994 0.056 Uiso 1 1 calc R . .
C20 C -0.4113(5) 0.7922(6) 0.3925(5) 0.073(3) Uani 1 1 d . . .
H20A H -0.3916 0.7842 0.4530 0.109 Uiso 1 1 calc R . .
H20B H -0.4751 0.7877 0.3636 0.109 Uiso 1 1 calc R . .
H20C H -0.3930 0.8528 0.3818 0.109 Uiso 1 1 calc R . .
N4 N 0.1312(3) 0.7710(3) 0.2905(3) 0.0266(11) Uani 1 1 d . . .
C21 C 0.1757(4) 0.8590(4) 0.2808(3) 0.0300(14) Uani 1 1 d . . .
H21A H 0.1951 0.8484 0.2364 0.036 Uiso 1 1 calc R . .
H21B H 0.1317 0.9089 0.2611 0.036 Uiso 1 1 calc R . .
C22 C 0.2538(4) 0.8923(4) 0.3593(4) 0.0348(15) Uani 1 1 d . . .
H22A H 0.2961 0.8414 0.3833 0.042 Uiso 1 1 calc R . .
H22B H 0.2342 0.9118 0.4018 0.042 Uiso 1 1 calc R . .
C23 C 0.2980(4) 0.9734(5) 0.3376(4) 0.0406(17) Uani 1 1 d . . .
H23A H 0.2527 1.0188 0.3041 0.049 Uiso 1 1 calc R . .
H23B H 0.3384 1.0039 0.3903 0.049 Uiso 1 1 calc R . .
C24 C 0.3476(4) 0.9464(6) 0.2896(5) 0.057(2) Uani 1 1 d . . .
H24A H 0.3913 0.8999 0.3214 0.085 Uiso 1 1 calc R . .
H24B H 0.3768 1.0006 0.2809 0.085 Uiso 1 1 calc R . .
H24C H 0.3072 0.9209 0.2351 0.085 Uiso 1 1 calc R . .
C25 C 0.1939(4) 0.6911(4) 0.3161(4) 0.0327(15) Uani 1 1 d . . .
H25A H 0.1618 0.6353 0.3188 0.039 Uiso 1 1 calc R . .
H25B H 0.2397 0.7030 0.3736 0.039 Uiso 1 1 calc R . .
C26 C 0.2382(4) 0.6701(5) 0.2605(4) 0.0409(17) Uani 1 1 d . . .
H26A H 0.1933 0.6621 0.2019 0.049 Uiso 1 1 calc R . .
H26B H 0.2755 0.7229 0.2618 0.049 Uiso 1 1 calc R . .
C27 C 0.2933(5) 0.5844(5) 0.2884(5) 0.053(2) Uani 1 1 d . . .
H27A H 0.2560 0.5327 0.2895 0.063 Uiso 1 1 calc R . .
H27B H 0.3390 0.5937 0.3465 0.063 Uiso 1 1 calc R . .
C28 C 0.3365(5) 0.5583(6) 0.2333(5) 0.069(3) Uani 1 1 d . . .
H28A H 0.2918 0.5478 0.1758 0.104 Uiso 1 1 calc R . .
H28B H 0.3708 0.5020 0.2549 0.104 Uiso 1 1 calc R . .
H28C H 0.3752 0.6083 0.2333 0.104 Uiso 1 1 calc R . .
C29 C 0.1003(4) 0.7829(4) 0.3582(3) 0.0305(14) Uani 1 1 d . . .
H29A H 0.0801 0.7224 0.3685 0.037 Uiso 1 1 calc R . .
H29B H 0.1510 0.8015 0.4108 0.037 Uiso 1 1 calc R . .
C30 C 0.0283(4) 0.8518(4) 0.3400(3) 0.0263(13) Uani 1 1 d . . .
H30A H -0.0265 0.8283 0.2943 0.032 Uiso 1 1 calc R . .
H30B H 0.0434 0.9102 0.3209 0.032 Uiso 1 1 calc R . .
C31 C 0.0139(4) 0.8698(4) 0.4180(4) 0.0304(14) Uani 1 1 d . . .
H31A H 0.0047 0.8104 0.4403 0.036 Uiso 1 1 calc R . .
H31B H 0.0671 0.8986 0.4618 0.036 Uiso 1 1 calc R . .
C32 C -0.0643(4) 0.9325(5) 0.3996(4) 0.0416(17) Uani 1 1 d . . .
H32A H -0.0567 0.9903 0.3751 0.062 Uiso 1 1 calc R . .
H32B H -0.0686 0.9455 0.4519 0.062 Uiso 1 1 calc R . .
H32C H -0.1178 0.9019 0.3600 0.062 Uiso 1 1 calc R . .
C33 C 0.0547(4) 0.7563(4) 0.2042(3) 0.0281(14) Uani 1 1 d . . .
H33A H 0.0178 0.8122 0.1894 0.034 Uiso 1 1 calc R . .
H33B H 0.0784 0.7499 0.1625 0.034 Uiso 1 1 calc R . .
C34 C -0.0029(4) 0.6739(4) 0.1960(4) 0.0299(14) Uani 1 1 d . . .
H34A H -0.0274 0.6781 0.2373 0.036 Uiso 1 1 calc R . .
H34B H 0.0313 0.6163 0.2065 0.036 Uiso 1 1 calc R . .
C35 C -0.0768(4) 0.6746(4) 0.1061(4) 0.0347(15) Uani 1 1 d . . .
H35A H -0.1081 0.7342 0.0958 0.042 Uiso 1 1 calc R . .
H35B H -0.0512 0.6695 0.0658 0.042 Uiso 1 1 calc R . .
C36 C -0.1421(4) 0.5965(5) 0.0901(4) 0.0443(17) Uani 1 1 d . . .
H36A H -0.1127 0.5373 0.0950 0.066 Uiso 1 1 calc R . .
H36B H -0.1899 0.6026 0.0334 0.066 Uiso 1 1 calc R . .
H36C H -0.1657 0.5995 0.1315 0.066 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
Cl1 0.0320(8) 0.0374(9) 0.0267(8) -0.0076(7) 0.0124(6) 0.0021(7)
F1 0.034(2) 0.047(2) 0.054(2) -0.0297(19) 0.0166(18) -0.0087(18)
F2 0.062(3) 0.044(3) 0.064(3) -0.019(2) 0.001(2) 0.026(2)
F3 0.116(4) 0.063(3) 0.065(3) -0.030(2) 0.073(3) -0.034(3)
O1 0.026(2) 0.030(2) 0.028(2) -0.011(2) 0.0082(18) -0.0027(18)
N1 0.027(3) 0.034(3) 0.029(3) -0.008(2) 0.013(2) -0.001(2)
N2 0.025(3) 0.029(3) 0.028(3) -0.006(2) 0.009(2) -0.003(2)
N3 0.028(3) 0.030(3) 0.032(3) -0.008(2) 0.011(2) 0.002(2)
C1 0.096(7) 0.066(7) 0.098(8) -0.011(6) -0.006(6) 0.010(6)
C2 0.062(5) 0.064(6) 0.061(5) 0.005(5) 0.011(4) 0.005(4)
C3 0.036(4) 0.070(6) 0.065(5) -0.024(5) 0.009(4) 0.002(4)
C4 0.027(3) 0.058(5) 0.041(4) -0.019(4) 0.011(3) -0.010(3)
C5 0.023(3) 0.040(4) 0.029(3) -0.005(3) 0.012(3) -0.003(3)
C6 0.021(3) 0.041(4) 0.025(3) 0.002(3) 0.008(3) 0.003(3)
C7 0.028(3) 0.023(3) 0.024(3) 0.006(3) 0.012(3) 0.006(3)
C8 0.028(3) 0.022(3) 0.036(3) 0.002(3) 0.020(3) 0.000(3)
C9 0.024(3) 0.022(3) 0.027(3) 0.002(3) 0.012(3) 0.004(2)
C10 0.016(3) 0.028(3) 0.017(3) 0.003(2) 0.003(2) 0.001(2)
C11 0.025(3) 0.025(3) 0.025(3) 0.004(3) 0.014(3) 0.001(3)
C12 0.025(3) 0.032(4) 0.022(3) 0.002(3) 0.011(3) 0.003(3)
C13 0.029(3) 0.028(4) 0.033(3) -0.008(3) 0.017(3) -0.002(3)
C14 0.025(3) 0.023(3) 0.027(3) 0.001(3) 0.013(3) -0.004(3)
C15 0.020(3) 0.031(4) 0.029(3) 0.000(3) 0.009(3) -0.006(3)
C16 0.026(3) 0.030(4) 0.031(3) 0.001(3) 0.016(3) 0.000(3)
C17 0.025(3) 0.028(4) 0.027(3) 0.003(3) 0.012(3) -0.002(3)
C18 0.033(3) 0.038(4) 0.034(3) 0.009(3) 0.017(3) 0.009(3)
C19 0.034(3) 0.070(6) 0.042(4) 0.023(4) 0.022(3) 0.020(4)
C20 0.061(5) 0.109(8) 0.059(5) 0.020(5) 0.036(4) 0.045(5)
N4 0.033(3) 0.023(3) 0.025(3) 0.006(2) 0.014(2) 0.005(2)
C21 0.034(3) 0.029(4) 0.027(3) 0.004(3) 0.013(3) -0.001(3)
C22 0.036(3) 0.031(4) 0.031(4) 0.001(3) 0.009(3) 0.001(3)
C23 0.030(3) 0.040(4) 0.045(4) 0.001(3) 0.010(3) 0.003(3)
C24 0.047(4) 0.060(6) 0.071(5) 0.004(4) 0.033(4) -0.003(4)
C25 0.036(3) 0.033(4) 0.031(3) 0.011(3) 0.016(3) 0.008(3)
C26 0.047(4) 0.041(4) 0.046(4) 0.017(3) 0.030(3) 0.018(3)
C27 0.064(5) 0.051(5) 0.063(5) 0.021(4) 0.047(4) 0.023(4)
C28 0.089(6) 0.068(6) 0.081(6) 0.026(5) 0.065(5) 0.030(5)
C29 0.034(3) 0.038(4) 0.021(3) 0.005(3) 0.013(3) 0.002(3)
C30 0.028(3) 0.025(3) 0.026(3) 0.001(3) 0.011(3) 0.001(3)
C31 0.036(3) 0.029(4) 0.031(3) -0.002(3) 0.018(3) -0.003(3)
C32 0.048(4) 0.041(4) 0.042(4) -0.004(3) 0.026(3) 0.002(3)
C33 0.031(3) 0.031(4) 0.022(3) 0.002(3) 0.011(3) 0.003(3)
C34 0.042(3) 0.023(4) 0.033(3) 0.003(3) 0.024(3) 0.000(3)
C35 0.038(3) 0.030(4) 0.035(4) 0.002(3) 0.015(3) 0.001(3)
C36 0.046(4) 0.032(4) 0.052(4) -0.005(3) 0.018(4) -0.004(3)

_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
F1 C13 1.344(6) . ?
F2 C13 1.332(7) . ?
F3 C13 1.335(7) . ?
O1 C14 1.224(6) . ?
N1 C12 1.372(7) . ?
N1 C5 1.382(7) . ?
N2 C14 1.392(7) . ?
N2 C11 1.401(7) . ?
N3 C14 1.354(7) . ?
N3 C15 1.455(6) . ?
C1 C2 1.570(12) . ?
C2 C3 1.492(11) . ?
C3 C4 1.497(10) . ?
C4 C5 1.502(8) . ?
C5 C6 1.372(8) . ?
C6 C7 1.424(8) . ?
C7 C8 1.402(8) . ?
C7 C12 1.403(7) . ?
C8 C9 1.380(8) . ?
C9 C10 1.408(7) . ?
C9 C13 1.481(8) . ?
C10 C11 1.393(8) . ?
C11 C12 1.409(8) . ?
C15 C16 1.513(8) . ?
C16 C17 1.529(7) . ?
C17 C18 1.519(8) . ?
C18 C19 1.515(8) . ?
C19 C20 1.527(10) . ?
N4 C25 1.507(7) . ?
N4 C29 1.517(7) . ?
N4 C33 1.527(7) . ?
N4 C21 1.535(7) . ?
C21 C22 1.521(8) . ?
C22 C23 1.536(9) . ?
C23 C24 1.490(9) . ?
C25 C26 1.512(8) . ?
C26 C27 1.506(9) . ?
C27 C28 1.508(9) . ?
C29 C30 1.505(8) . ?
C30 C31 1.527(8) . ?
C31 C32 1.527(8) . ?
C33 C34 1.514(8) . ?
C34 C35 1.538(8) . ?
C35 C36 1.527(8) . ?

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
C12 N1 C5 108.9(5) . . ?
C14 N2 C11 127.7(5) . . ?
C14 N3 C15 121.6(5) . . ?
C3 C2 C1 114.1(8) . . ?
C2 C3 C4 113.4(7) . . ?
C3 C4 C5 114.6(6) . . ?
C6 C5 N1 108.8(5) . . ?
C6 C5 C4 130.1(5) . . ?
N1 C5 C4 121.1(5) . . ?
C5 C6 C7 107.5(5) . . ?
C8 C7 C12 119.1(5) . . ?
C8 C7 C6 134.2(5) . . ?
C12 C7 C6 106.7(5) . . ?
C9 C8 C7 118.1(5) . . ?
C8 C9 C10 123.0(5) . . ?
C8 C9 C13 117.6(5) . . ?
C10 C9 C13 119.3(5) . . ?
C11 C10 C9 119.8(5) . . ?
C10 C11 N2 125.9(5) . . ?
C10 C11 C12 117.1(5) . . ?
N2 C11 C12 117.1(5) . . ?
N1 C12 C7 108.1(5) . . ?
N1 C12 C11 128.9(5) . . ?
C7 C12 C11 123.0(5) . . ?
F2 C13 F3 105.1(5) . . ?
F2 C13 F1 104.7(5) . . ?
F3 C13 F1 104.7(5) . . ?
F2 C13 C9 114.1(5) . . ?
F3 C13 C9 113.1(5) . . ?
F1 C13 C9 114.2(5) . . ?
O1 C14 N3 123.2(5) . . ?
O1 C14 N2 124.1(5) . . ?
N3 C14 N2 112.7(5) . . ?
N3 C15 C16 110.7(5) . . ?
C15 C16 C17 112.2(5) . . ?
C18 C17 C16 113.1(5) . . ?
C19 C18 C17 113.2(5) . . ?
C18 C19 C20 113.3(6) . . ?
C25 N4 C29 107.2(4) . . ?
C25 N4 C33 112.0(4) . . ?
C29 N4 C33 111.6(4) . . ?
C25 N4 C21 110.8(4) . . ?
C29 N4 C21 110.7(4) . . ?
C33 N4 C21 104.5(4) . . ?
C22 C21 N4 116.1(5) . . ?
C21 C22 C23 110.1(5) . . ?
C24 C23 C22 113.8(6) . . ?
N4 C25 C26 116.7(5) . . ?
C27 C26 C25 111.7(5) . . ?
C26 C27 C28 114.0(6) . . ?
C30 C29 N4 116.1(4) . . ?
C29 C30 C31 111.0(5) . . ?
C32 C31 C30 112.3(5) . . ?
C34 C33 N4 116.0(5) . . ?
C33 C34 C35 107.2(5) . . ?
C36 C35 C34 112.7(5) . . ?

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 Cl1 0.88 2.34 3.208(5) 166.7 .
N2 H2 Cl1 0.88 2.27 3.140(5) 170.1 .
N3 H3 Cl1 0.88 2.61 3.406(5) 151.2 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.080


data_2011sot0559
_database_code_depnum_ccdc_archive 'CCDC 879845'
#TrackingRef '- combined structures.cif'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   19.510(13)
_cell_length_b                   4.657(3)
_cell_length_c                   16.320(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.506(16)
_cell_angle_gamma                90.00
_cell_volume                     1414.13
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N1 N 0.05898(13) 0.1221(5) 0.38951(15)
H1 H 0.0634 0.3074 0.3818
F1 F -0.23865(10) -0.5220(4) 0.33475(12)
O1 O 0.12051(11) -0.3010(4) 0.43044(13)
N2 N 0.18162(13) 0.1207(5) 0.45290(15)
H2 H 0.1799 0.3091 0.4486
C2 C -0.15132(17) -0.2001(6) 0.31445(19)
C5 C -0.01103(16) 0.0066(6) 0.36424(18)
C10 C 0.31275(17) 0.1903(6) 0.5148(2)
H10A H 0.3164 0.2898 0.4627
H10B H 0.3035 0.3369 0.5541
C4 C -0.06176(17) 0.1158(6) 0.29128(19)
H4 H -0.0483 0.2619 0.2585
C6 C -0.03177(17) -0.2053(6) 0.41219(19)
H6 H 0.0021 -0.2795 0.4624
F3 F -0.27520(10) -0.1049(4) 0.28753(15)
C7 C -0.10155(17) -0.3080(6) 0.38688(19)
H7 H -0.1153 -0.4538 0.4196
C9 C 0.25071(16) -0.0204(6) 0.49010(19)
H9A H 0.2588 -0.1596 0.4481
H9B H 0.2494 -0.1290 0.5418
C8 C 0.12058(17) -0.0316(6) 0.42509(18)
F2 F -0.24614(11) -0.4109(5) 0.20522(12)
C3 C -0.13117(17) 0.0138(6) 0.26630(19)
H3 H -0.1653 0.0887 0.2164
C1 C -0.22661(18) -0.3059(7) 0.2859(2)
C12 C 0.44722(17) 0.2386(7) 0.5918(2)
H12A H 0.4374 0.3729 0.6340
H12B H 0.4531 0.3539 0.5434
C11 C 0.38316(17) 0.0394(6) 0.5585(2)
H11A H 0.3936 -0.0965 0.5171
H11B H 0.3774 -0.0744 0.6072
C13 C 0.51713(18) 0.0790(7) 0.6343(2)
H13A H 0.5109 -0.0393 0.6819
H13B H 0.5273 -0.0526 0.5917
C14 C 0.5814(2) 0.2777(8) 0.6694(3)
H14A H 0.5899 0.3869 0.6221
H14B H 0.6241 0.1631 0.6977
H14C H 0.5715 0.4106 0.7110

#END