data_2013ncs0116
_audit_creation_date              2013-08-14
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.04.25 svn.r2679, GUI svn.r4466)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_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/[σ²(Fo²)+(0.1555P)²+0.1171P] where P=(Fo²+2Fc²)/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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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 . . .


_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 . . ?

