# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics
# This journal is © The Owner Societies 2013

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#                                CCDC 
# 
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#  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.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_2013ncs0116
_audit_creation_date             2013-08-14
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H29 N2 S, F6 P'
_chemical_formula_sum            'C21 H29 F6 N2 P S'
_chemical_formula_weight         486.49
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   8.459(3)
_cell_length_b                   15.354(6)
_cell_length_c                   8.964(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.690(12)
_cell_angle_gamma                90.00
_cell_volume                     1160.3(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9448
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         5.73
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3698
_reflns_number_total             3719
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(19)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3719
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1555P)^2^+0.1171P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1692
_refine_ls_wR_factor_ref         0.1695
_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^ > 2sigma(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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C016(H016), C018(H018)
2.b Secondary CH2 refined with riding coordinates:
 C019(H01D,H01E), C020(H02A,H02B), C024(H02F,H02G)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C011(H011), C012(H012), C015(H015), C017(H017), C021(H021),
 C023(H023), C025(H025), C028(H028), C029(H029)
2.d Idealised Me refined as rotating group:
 C014(H01A,H01B,H01C), C022(H02C,H02D,H02E), C027(H02H,H02I,H02J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.59357(8) 0.43923(6) 0.02018(8) 0.0260(2) Uani 1 1 d . . .
P2 P 0.14144(9) 0.23775(5) -0.00598(9) 0.0247(3) Uani 1 1 d . . .
F001 F 0.1020(3) 0.23305(17) -0.1835(2) 0.0394(5) Uani 1 1 d . . .
F002 F -0.0143(2) 0.29541(15) 0.0056(2) 0.0350(5) Uani 1 1 d . . .
F003 F 0.1760(4) 0.2420(2) 0.1710(3) 0.0564(7) Uani 1 1 d . . .
F004 F 0.0392(3) 0.15008(15) 0.0115(3) 0.0412(6) Uani 1 1 d . . .
F005 F 0.2443(3) 0.32291(16) -0.0246(3) 0.0468(6) Uani 1 1 d . . .
F006 F 0.2950(3) 0.17821(18) -0.0214(4) 0.0537(7) Uani 1 1 d . . .
N007 N 0.7465(3) 0.37425(17) 0.2627(3) 0.0219(6) Uani 1 1 d . . .
N008 N 0.8874(3) 0.47713(18) 0.1407(3) 0.0203(5) Uani 1 1 d . . .
C009 C 1.0559(4) 0.5321(3) 0.6920(4) 0.0298(7) Uani 1 1 d . . .
H009 H 1.0618 0.5486 0.7945 0.036 Uiso 1 1 calc R . .
C010 C 0.7572(3) 0.4302(2) 0.1518(3) 0.0201(6) Uani 1 1 d . . .
C011 C 0.5471(4) 0.2384(2) 0.7250(4) 0.0289(7) Uani 1 1 d . . .
H011 H 0.5291 0.2232 0.8249 0.035 Uiso 1 1 calc R . .
C012 C 0.7267(4) 0.2759(2) 0.5406(4) 0.0260(7) Uani 1 1 d . . .
H012 H 0.8320 0.2855 0.5148 0.031 Uiso 1 1 calc R . .
C013 C 1.0394(3) 0.4842(2) 0.3912(3) 0.0193(6) Uani 1 1 d . . .
C014 C 0.4854(5) 0.5228(2) -0.5414(4) 0.0310(8) Uani 1 1 d . . .
H01A H 0.5308 0.5447 -0.6313 0.046 Uiso 1 1 calc R . .
H01B H 0.3979 0.5608 -0.5170 0.046 Uiso 1 1 calc R . .
H01C H 0.4455 0.4636 -0.5598 0.046 Uiso 1 1 calc R . .
C015 C 1.0883(3) 0.4245(2) 0.5024(3) 0.0229(7) Uani 1 1 d . . .
H015 H 1.1157 0.3669 0.4755 0.028 Uiso 1 1 calc R . .
C016 C 0.6232(4) 0.3065(2) 0.2703(3) 0.0223(7) Uani 1 1 d . . .
H016 H 0.5211 0.3306 0.2234 0.027 Uiso 1 1 calc R . .
C017 C 1.0973(4) 0.4483(2) 0.6523(4) 0.0283(7) Uani 1 1 d . . .
H017 H 1.1318 0.4074 0.7275 0.034 Uiso 1 1 calc R . .
C018 C 1.0400(4) 0.45789(19) 0.2292(3) 0.0195(6) Uani 1 1 d . . .
H018 H 1.0590 0.3937 0.2252 0.023 Uiso 1 1 calc R . .
C019 C 0.5489(4) 0.4858(2) -0.2695(4) 0.0239(6) Uani 1 1 d . . .
H01D H 0.4597 0.5222 -0.2410 0.029 Uiso 1 1 calc R . .
H01E H 0.5088 0.4259 -0.2882 0.029 Uiso 1 1 calc R . .
C020 C 0.6122(4) 0.5220(2) -0.4116(4) 0.0271(7) Uani 1 1 d . . .
H02A H 0.6513 0.5821 -0.3925 0.033 Uiso 1 1 calc R . .
H02B H 0.7027 0.4860 -0.4385 0.033 Uiso 1 1 calc R . .
C021 C 0.4194(4) 0.2459(2) 0.6173(4) 0.0289(7) Uani 1 1 d . . .
H021 H 0.3144 0.2355 0.6433 0.035 Uiso 1 1 calc R . .
C022 C 0.6643(5) 0.2254(2) 0.1819(4) 0.0307(7) Uani 1 1 d . . .
H02C H 0.6754 0.2415 0.0774 0.046 Uiso 1 1 calc R . .
H02D H 0.5795 0.1822 0.1859 0.046 Uiso 1 1 calc R . .
H02E H 0.7643 0.2007 0.2256 0.046 Uiso 1 1 calc R . .
C023 C 0.9971(4) 0.5686(2) 0.4321(4) 0.0244(6) Uani 1 1 d . . .
H023 H 0.9626 0.6098 0.3573 0.029 Uiso 1 1 calc R . .
C024 C 0.6793(4) 0.4847(2) -0.1428(3) 0.0233(6) Uani 1 1 d . . .
H02F H 0.7184 0.5446 -0.1212 0.028 Uiso 1 1 calc R . .
H02G H 0.7693 0.4485 -0.1701 0.028 Uiso 1 1 calc R . .
C025 C 1.0057(4) 0.5918(2) 0.5819(4) 0.0293(7) Uani 1 1 d . . .
H025 H 0.9770 0.6491 0.6095 0.035 Uiso 1 1 calc R . .
C026 C 0.5998(4) 0.2847(2) 0.4319(3) 0.0212(6) Uani 1 1 d . . .
C027 C 1.1726(4) 0.5039(3) 0.1521(3) 0.0274(7) Uani 1 1 d . . .
H02H H 1.1634 0.4895 0.0452 0.041 Uiso 1 1 calc R . .
H02I H 1.2760 0.4845 0.1974 0.041 Uiso 1 1 calc R . .
H02J H 1.1630 0.5671 0.1645 0.041 Uiso 1 1 calc R . .
C028 C 0.6996(4) 0.2531(2) 0.6868(4) 0.0289(7) Uani 1 1 d . . .
H028 H 0.7864 0.2476 0.7604 0.035 Uiso 1 1 calc R . .
C029 C 0.4468(4) 0.2688(2) 0.4718(4) 0.0247(7) Uani 1 1 d . . .
H029 H 0.3598 0.2736 0.3982 0.030 Uiso 1 1 calc R . .
H007 H 0.825(6) 0.375(3) 0.347(6) 0.035(11) Uiso 1 1 d . . .
H008 H 0.889(7) 0.522(4) 0.072(7) 0.053(15) Uiso 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 0.0195(4) 0.0399(5) 0.0182(4) 0.0061(3) -0.0006(3) -0.0038(3)
P2 0.0245(4) 0.0234(4) 0.0263(5) 0.0008(3) 0.0032(3) -0.0025(3)
F001 0.0492(13) 0.0450(12) 0.0258(11) -0.0085(10) 0.0139(9) -0.0040(10)
F002 0.0335(11) 0.0426(11) 0.0293(10) -0.0086(9) 0.0053(8) 0.0077(9)
F003 0.0742(18) 0.0642(17) 0.0274(13) 0.0064(12) -0.0168(12) -0.0028(15)
F004 0.0450(12) 0.0300(11) 0.0512(14) 0.0000(9) 0.0209(10) -0.0102(9)
F005 0.0417(12) 0.0353(12) 0.0618(17) 0.0070(10) -0.0058(11) -0.0158(10)
F006 0.0377(13) 0.0463(14) 0.0795(19) 0.0221(13) 0.0186(12) 0.0137(11)
N007 0.0231(12) 0.0272(14) 0.0155(13) 0.0026(10) 0.0013(11) -0.0030(10)
N008 0.0202(13) 0.0278(13) 0.0125(11) 0.0025(10) -0.0003(9) -0.0032(10)
C009 0.0313(17) 0.0438(19) 0.0149(14) -0.0046(13) 0.0049(12) -0.0107(15)
C010 0.0218(14) 0.0257(15) 0.0131(12) -0.0005(12) 0.0027(10) 0.0008(12)
C011 0.0409(19) 0.0255(15) 0.0213(15) 0.0006(12) 0.0084(14) -0.0033(14)
C012 0.0219(15) 0.0327(16) 0.0230(16) 0.0035(13) 0.0006(12) -0.0027(12)
C013 0.0155(13) 0.0266(15) 0.0156(15) -0.0024(11) 0.0005(11) -0.0024(11)
C014 0.0368(19) 0.0344(18) 0.0200(16) 0.0064(13) -0.0076(15) -0.0032(14)
C015 0.0229(15) 0.0238(16) 0.0219(16) 0.0025(12) 0.0001(12) -0.0011(11)
C016 0.0228(15) 0.0263(15) 0.0178(15) 0.0016(12) 0.0020(12) -0.0058(11)
C017 0.0269(15) 0.0398(18) 0.0179(14) 0.0096(13) -0.0007(12) -0.0068(14)
C018 0.0190(14) 0.0258(15) 0.0137(13) -0.0034(11) 0.0003(10) 0.0012(10)
C019 0.0258(15) 0.0251(16) 0.0201(15) 0.0006(12) -0.0024(12) -0.0013(11)
C020 0.0320(17) 0.0310(17) 0.0174(15) 0.0017(12) -0.0040(13) -0.0039(13)
C021 0.0309(16) 0.0320(16) 0.0252(17) -0.0010(13) 0.0109(13) -0.0055(14)
C022 0.0399(19) 0.0304(17) 0.0219(16) -0.0028(13) 0.0028(14) -0.0054(13)
C023 0.0291(15) 0.0245(14) 0.0198(14) 0.0000(12) 0.0029(12) -0.0001(12)
C024 0.0212(14) 0.0298(16) 0.0187(15) 0.0025(12) 0.0006(12) -0.0062(12)
C025 0.0305(17) 0.0295(17) 0.0289(17) -0.0051(15) 0.0075(13) -0.0029(13)
C026 0.0238(15) 0.0214(14) 0.0188(15) 0.0014(12) 0.0034(12) -0.0009(11)
C027 0.0208(15) 0.0457(18) 0.0164(15) 0.0002(13) 0.0053(12) -0.0034(13)
C028 0.0354(18) 0.0278(16) 0.0229(16) 0.0032(12) -0.0007(13) -0.0005(13)
C029 0.0247(15) 0.0255(15) 0.0239(16) -0.0004(12) 0.0026(12) -0.0016(12)

_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 C010 1.749(3) . ?
S1 C024 1.822(3) . ?
P2 F001 1.600(2) . ?
P2 F002 1.598(2) . ?
P2 F003 1.591(2) . ?
P2 F004 1.615(2) . ?
P2 F005 1.587(2) . ?
P2 F006 1.604(3) . ?
N007 C010 1.322(4) . ?
N007 C016 1.478(4) . ?
N007 H007 0.97(5) . ?
N008 C010 1.327(4) . ?
N008 C018 1.488(4) . ?
N008 H008 0.92(6) . ?
C009 H009 0.9500 . ?
C009 C017 1.387(6) . ?
C009 C025 1.388(5) . ?
C011 H011 0.9500 . ?
C011 C021 1.393(5) . ?
C011 C028 1.380(5) . ?
C012 H012 0.9500 . ?
C012 C026 1.396(5) . ?
C012 C028 1.394(5) . ?
C013 C015 1.392(4) . ?
C013 C018 1.508(4) . ?
C013 C023 1.402(4) . ?
C014 H01A 0.9800 . ?
C014 H01B 0.9800 . ?
C014 H01C 0.9800 . ?
C014 C020 1.517(5) . ?
C015 H015 0.9500 . ?
C015 C017 1.389(5) . ?
C016 H016 1.0000 . ?
C016 C022 1.531(5) . ?
C016 C026 1.515(4) . ?
C017 H017 0.9500 . ?
C018 H018 1.0000 . ?
C018 C027 1.537(4) . ?
C019 H01D 0.9900 . ?
C019 H01E 0.9900 . ?
C019 C020 1.527(4) . ?
C019 C024 1.517(4) . ?
C020 H02A 0.9900 . ?
C020 H02B 0.9900 . ?
C021 H021 0.9500 . ?
C021 C029 1.389(5) . ?
C022 H02C 0.9800 . ?
C022 H02D 0.9800 . ?
C022 H02E 0.9800 . ?
C023 H023 0.9500 . ?
C023 C025 1.386(5) . ?
C024 H02F 0.9900 . ?
C024 H02G 0.9900 . ?
C025 H025 0.9500 . ?
C026 C029 1.392(5) . ?
C027 H02H 0.9800 . ?
C027 H02I 0.9800 . ?
C027 H02J 0.9800 . ?
C028 H028 0.9500 . ?
C029 H029 0.9500 . ?

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
C010 S1 C024 103.08(14) . . ?
F001 P2 F004 89.38(13) . . ?
F001 P2 F006 89.59(15) . . ?
F002 P2 F001 89.08(12) . . ?
F002 P2 F004 90.25(14) . . ?
F002 P2 F006 178.32(16) . . ?
F003 P2 F001 178.56(15) . . ?
F003 P2 F002 89.88(14) . . ?
F003 P2 F004 89.63(15) . . ?
F003 P2 F006 91.43(17) . . ?
F005 P2 F001 90.22(14) . . ?
F005 P2 F002 90.72(14) . . ?
F005 P2 F003 90.79(16) . . ?
F005 P2 F004 178.95(15) . . ?
F005 P2 F006 90.32(15) . . ?
F006 P2 F004 88.70(14) . . ?
C010 N007 C016 125.7(3) . . ?
C010 N007 H007 119(3) . . ?
C016 N007 H007 115(3) . . ?
C010 N008 C018 122.8(3) . . ?
C010 N008 H008 121(4) . . ?
C018 N008 H008 116(4) . . ?
C017 C009 H009 120.0 . . ?
C017 C009 C025 119.9(3) . . ?
C025 C009 H009 120.0 . . ?
N007 C010 S1 117.4(2) . . ?
N007 C010 N008 121.2(3) . . ?
N008 C010 S1 121.5(2) . . ?
C021 C011 H011 119.9 . . ?
C028 C011 H011 119.9 . . ?
C028 C011 C021 120.2(3) . . ?
C026 C012 H012 119.8 . . ?
C028 C012 H012 119.8 . . ?
C028 C012 C026 120.3(3) . . ?
C015 C013 C018 119.3(3) . . ?
C015 C013 C023 119.3(3) . . ?
C023 C013 C018 121.4(3) . . ?
H01A C014 H01B 109.5 . . ?
H01A C014 H01C 109.5 . . ?
H01B C014 H01C 109.5 . . ?
C020 C014 H01A 109.5 . . ?
C020 C014 H01B 109.5 . . ?
C020 C014 H01C 109.5 . . ?
C013 C015 H015 119.7 . . ?
C017 C015 C013 120.6(3) . . ?
C017 C015 H015 119.7 . . ?
N007 C016 H016 107.9 . . ?
N007 C016 C022 110.9(3) . . ?
N007 C016 C026 110.3(3) . . ?
C022 C016 H016 107.9 . . ?
C026 C016 H016 107.9 . . ?
C026 C016 C022 111.6(3) . . ?
C009 C017 C015 119.8(3) . . ?
C009 C017 H017 120.1 . . ?
C015 C017 H017 120.1 . . ?
N008 C018 C013 112.9(2) . . ?
N008 C018 H018 108.2 . . ?
N008 C018 C027 107.6(2) . . ?
C013 C018 H018 108.2 . . ?
C013 C018 C027 111.7(3) . . ?
C027 C018 H018 108.2 . . ?
H01D C019 H01E 108.1 . . ?
C020 C019 H01D 109.6 . . ?
C020 C019 H01E 109.6 . . ?
C024 C019 H01D 109.6 . . ?
C024 C019 H01E 109.6 . . ?
C024 C019 C020 110.2(3) . . ?
C014 C020 C019 111.6(3) . . ?
C014 C020 H02A 109.3 . . ?
C014 C020 H02B 109.3 . . ?
C019 C020 H02A 109.3 . . ?
C019 C020 H02B 109.3 . . ?
H02A C020 H02B 108.0 . . ?
C011 C021 H021 120.3 . . ?
C029 C021 C011 119.5(3) . . ?
C029 C021 H021 120.3 . . ?
C016 C022 H02C 109.5 . . ?
C016 C022 H02D 109.5 . . ?
C016 C022 H02E 109.5 . . ?
H02C C022 H02D 109.5 . . ?
H02C C022 H02E 109.5 . . ?
H02D C022 H02E 109.5 . . ?
C013 C023 H023 120.1 . . ?
C025 C023 C013 119.8(3) . . ?
C025 C023 H023 120.1 . . ?
S1 C024 H02F 110.3 . . ?
S1 C024 H02G 110.3 . . ?
C019 C024 S1 106.9(2) . . ?
C019 C024 H02F 110.3 . . ?
C019 C024 H02G 110.3 . . ?
H02F C024 H02G 108.6 . . ?
C009 C025 H025 119.7 . . ?
C023 C025 C009 120.6(3) . . ?
C023 C025 H025 119.7 . . ?
C012 C026 C016 122.4(3) . . ?
C029 C026 C012 118.8(3) . . ?
C029 C026 C016 118.7(3) . . ?
C018 C027 H02H 109.5 . . ?
C018 C027 H02I 109.5 . . ?
C018 C027 H02J 109.5 . . ?
H02H C027 H02I 109.5 . . ?
H02H C027 H02J 109.5 . . ?
H02I C027 H02J 109.5 . . ?
C011 C028 C012 120.2(3) . . ?
C011 C028 H028 119.9 . . ?
C012 C028 H028 119.9 . . ?
C021 C029 C026 121.1(3) . . ?
C021 C029 H029 119.5 . . ?
C026 C029 H029 119.5 . . ?

_database_code_depnum_ccdc_archive 'CCDC 955868'
#######################################################################
#
#                 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_2013ncs0121

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 Br N2 S'
_chemical_formula_weight         393.38

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'
Br Br -0.2901 2.4595 '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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   12.0601(8)
_cell_length_b                   12.5854(3)
_cell_length_c                   12.9527(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1965.98(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15819
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4486
_reflns_number_gt                3978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 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^ > 2sigma(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^)+(0.0132P)^2^+0.0000P] 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    mixed
_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   -0.006(5)
_refine_ls_number_reflns         4486
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0428
_refine_ls_wR_factor_gt          0.0407
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_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
Br1 Br -0.623843(14) -0.430681(14) -0.027047(13) 0.02270(5) Uani 1 1 d . . .
S1 S -0.52615(4) -0.74691(4) -0.24283(4) 0.02502(11) Uani 1 1 d . . .
N1 N -0.61201(11) -0.79769(11) -0.42674(10) 0.0182(3) Uani 1 1 d . . .
H1 H -0.5492 -0.8326 -0.4335 0.022 Uiso 1 1 calc R . .
C18 C -0.83604(15) -1.06040(16) -0.39927(14) 0.0281(4) Uani 1 1 d . . .
H18 H -0.8151 -1.1269 -0.3707 0.034 Uiso 1 1 calc R . .
N0AA N -0.70162(11) -0.66322(12) -0.33639(11) 0.0205(3) Uani 1 1 d . . .
H0AA H -0.7372 -0.6448 -0.3930 0.025 Uiso 1 1 calc R . .
C16 C -0.97709(14) -0.93794(16) -0.45052(14) 0.0276(4) Uani 1 1 d . . .
H16 H -1.0533 -0.9205 -0.4582 0.033 Uiso 1 1 calc R . .
C3 C -0.62295(14) -0.73600(13) -0.34474(12) 0.0181(4) Uani 1 1 d . . .
C8 C -0.85830(14) -0.74894(15) -0.00525(15) 0.0308(5) Uani 1 1 d . . .
H8 H -0.8492 -0.7485 0.0676 0.037 Uiso 1 1 calc R . .
C15 C -0.89679(12) -0.86595(13) -0.48122(14) 0.0216(4) Uani 1 1 d . . .
H15 H -0.9181 -0.7992 -0.5090 0.026 Uiso 1 1 calc R . .
C14 C -0.78443(12) -0.89118(12) -0.47145(14) 0.0164(3) Uani 1 1 d . . .
C10 C -0.52116(15) -0.89059(15) -0.22271(15) 0.0273(4) Uani 1 1 d . . .
H10A H -0.4999 -0.9255 -0.2882 0.033 Uiso 1 1 calc R . .
H10B H -0.4633 -0.9070 -0.1709 0.033 Uiso 1 1 calc R . .
C11 C -0.63108(16) -0.93611(16) -0.18620(14) 0.0366(5) Uani 1 1 d . . .
H11A H -0.6882 -0.9227 -0.2384 0.055 Uiso 1 1 calc R . .
H11B H -0.6525 -0.9021 -0.1211 0.055 Uiso 1 1 calc R . .
H11C H -0.6234 -1.0128 -0.1755 0.055 Uiso 1 1 calc R . .
C17 C -0.94766(15) -1.03475(16) -0.40891(15) 0.0290(5) Uani 1 1 d . . .
H17 H -1.0031 -1.0834 -0.3871 0.035 Uiso 1 1 calc R . .
C9 C -0.79106(14) -0.68538(14) -0.06574(14) 0.0227(4) Uani 1 1 d . . .
H9 H -0.7360 -0.6421 -0.0344 0.027 Uiso 1 1 calc R . .
C4 C -0.80394(13) -0.68466(14) -0.17255(14) 0.0198(4) Uani 1 1 d . . .
C13 C -0.64069(15) -0.84915(16) -0.60723(13) 0.0285(5) Uani 1 1 d . . .
H13A H -0.5876 -0.7949 -0.6297 0.043 Uiso 1 1 calc R . .
H13B H -0.6966 -0.8598 -0.6611 0.043 Uiso 1 1 calc R . .
H13C H -0.6015 -0.9161 -0.5946 0.043 Uiso 1 1 calc R . .
C5 C -0.88433(14) -0.75008(13) -0.21609(14) 0.0283(4) Uani 1 1 d . . .
H5 H -0.8937 -0.7509 -0.2889 0.034 Uiso 1 1 calc R . .
C12 C -0.69709(13) -0.81298(14) -0.50837(13) 0.0185(4) Uani 1 1 d . . .
H12 H -0.7339 -0.7431 -0.5217 0.022 Uiso 1 1 calc R . .
C19 C -0.75541(15) -0.98955(15) -0.43106(14) 0.0222(4) Uani 1 1 d . . .
H19 H -0.6794 -1.0083 -0.4252 0.027 Uiso 1 1 calc R . .
C2 C -0.79580(14) -0.50775(14) -0.26309(14) 0.0265(4) Uani 1 1 d . . .
H2A H -0.7494 -0.4631 -0.3075 0.040 Uiso 1 1 calc R . .
H2B H -0.8123 -0.4697 -0.1989 0.040 Uiso 1 1 calc R . .
H2C H -0.8652 -0.5245 -0.2989 0.040 Uiso 1 1 calc R . .
C6 C -0.73446(14) -0.61010(14) -0.23824(13) 0.0199(4) Uani 1 1 d . . .
H6 H -0.6656 -0.5918 -0.1990 0.024 Uiso 1 1 calc R . .
C7 C -0.93861(15) -0.81310(15) -0.04916(18) 0.0360(6) Uani 1 1 d . . .
H7 H -0.9848 -0.8561 -0.0069 0.043 Uiso 1 1 calc R . .
C1A C -0.95071(16) -0.81386(17) -0.15504(18) 0.0358(5) Uani 1 1 d . . .
H1A H -1.0049 -0.8584 -0.1861 0.043 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
Br1 0.02374(8) 0.02084(8) 0.02351(9) -0.00393(8) 0.00593(8) -0.00362(8)
S1 0.0220(2) 0.0295(3) 0.0236(2) -0.0020(2) -0.0082(2) 0.0025(2)
N1 0.0124(7) 0.0235(7) 0.0188(7) -0.0011(6) 0.0004(6) 0.0006(7)
C18 0.0379(10) 0.0218(10) 0.0245(10) 0.0041(9) 0.0012(8) -0.0020(9)
N0AA 0.0188(7) 0.0269(9) 0.0156(8) -0.0015(7) -0.0038(6) 0.0036(7)
C16 0.0198(8) 0.0299(10) 0.0331(11) -0.0058(10) 0.0023(8) -0.0027(9)
C3 0.0133(7) 0.0235(9) 0.0175(8) 0.0013(7) -0.0001(8) -0.0049(9)
C8 0.0328(11) 0.0305(10) 0.0292(10) 0.0058(8) 0.0063(9) 0.0065(9)
C15 0.0200(8) 0.0206(9) 0.0241(9) -0.0009(8) -0.0021(8) 0.0010(7)
C14 0.0182(8) 0.0192(8) 0.0118(8) -0.0036(8) -0.0004(8) -0.0025(7)
C10 0.0306(10) 0.0309(10) 0.0203(10) 0.0052(9) -0.0042(9) 0.0060(9)
C11 0.0437(11) 0.0424(12) 0.0238(10) 0.0102(10) 0.0022(10) -0.0069(14)
C17 0.0284(10) 0.0297(12) 0.0289(11) -0.0035(9) 0.0064(9) -0.0131(9)
C9 0.0197(9) 0.0239(10) 0.0246(10) -0.0003(8) 0.0004(8) 0.0022(8)
C4 0.0163(9) 0.0201(10) 0.0229(10) -0.0037(8) 0.0011(8) 0.0045(8)
C13 0.0262(10) 0.0422(12) 0.0170(10) -0.0034(9) 0.0026(9) -0.0098(10)
C5 0.0215(9) 0.0328(11) 0.0305(10) -0.0080(9) 0.0006(9) -0.0001(10)
C12 0.0171(8) 0.0228(9) 0.0157(10) 0.0005(7) -0.0005(7) -0.0001(7)
C19 0.0208(9) 0.0235(10) 0.0223(10) -0.0014(8) -0.0009(8) 0.0021(8)
C2 0.0301(10) 0.0261(10) 0.0234(10) -0.0007(9) 0.0000(9) 0.0029(9)
C6 0.0184(8) 0.0246(9) 0.0168(9) -0.0044(8) 0.0000(8) 0.0019(8)
C7 0.0284(10) 0.0251(11) 0.0546(16) 0.0087(11) 0.0155(10) 0.0013(9)
C1A 0.0242(10) 0.0285(12) 0.0546(15) -0.0111(10) 0.0049(10) -0.0065(9)

_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 C3 1.7675(16) . ?
S1 C10 1.8280(19) . ?
N1 C3 1.322(2) . ?
N1 C12 1.486(2) . ?
C18 C19 1.382(3) . ?
C18 C17 1.390(3) . ?
N0AA C3 1.323(2) . ?
N0AA C6 1.490(2) . ?
C16 C17 1.379(3) . ?
C16 C15 1.385(2) . ?
C8 C9 1.382(2) . ?
C8 C7 1.383(3) . ?
C15 C14 1.398(2) . ?
C14 C19 1.389(2) . ?
C14 C12 1.519(2) . ?
C10 C11 1.520(3) . ?
C9 C4 1.392(2) . ?
C4 C5 1.391(2) . ?
C4 C6 1.519(2) . ?
C13 C12 1.520(2) . ?
C5 C1A 1.382(3) . ?
C2 C6 1.520(2) . ?
C7 C1A 1.379(3) . ?

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
C3 S1 C10 101.83(8) . . ?
C3 N1 C12 125.36(14) . . ?
C19 C18 C17 120.32(19) . . ?
C3 N0AA C6 124.82(14) . . ?
C17 C16 C15 120.70(17) . . ?
N1 C3 N0AA 122.94(15) . . ?
N1 C3 S1 119.23(13) . . ?
N0AA C3 S1 117.79(12) . . ?
C9 C8 C7 121.03(19) . . ?
C16 C15 C14 120.23(17) . . ?
C19 C14 C15 118.75(16) . . ?
C19 C14 C12 121.43(14) . . ?
C15 C14 C12 119.77(15) . . ?
C11 C10 S1 112.87(14) . . ?
C16 C17 C18 119.32(18) . . ?
C8 C9 C4 120.10(18) . . ?
C5 C4 C9 118.47(17) . . ?
C5 C4 C6 121.53(17) . . ?
C9 C4 C6 119.95(16) . . ?
C1A C5 C4 121.02(19) . . ?
N1 C12 C14 109.79(14) . . ?
N1 C12 C13 109.22(12) . . ?
C14 C12 C13 112.43(14) . . ?
C18 C19 C14 120.66(17) . . ?
N0AA C6 C4 110.33(14) . . ?
N0AA C6 C2 109.20(14) . . ?
C4 C6 C2 111.95(14) . . ?
C1A C7 C8 119.14(19) . . ?
C7 C1A C5 120.23(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 955869'