#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/21/1512106.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1512106
loop_
_publ_author_name
'Poittevin, Clément'
'Liautard, Virginie'
'Beniazza, Redouane'
'Robert, Frédéric'
'Landais, Yannick'
_publ_section_title
;
 Free-Radical Carbo-alkenylation of Enamides and Ene-carbamates.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2814
_journal_page_last               2817
_journal_paper_doi               10.1021/ol401147w
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C21 H31 N O5 S Si'
_chemical_formula_sum            'C21 H31 N O5 S Si'
_chemical_formula_weight         437.62
_chemical_name_common            CP197PPf2'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.8080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7276(7)
_cell_length_b                   9.5070(6)
_cell_length_c                   20.4752(13)
_cell_measurement_reflns_used    5746
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.69
_cell_measurement_theta_min      1.77
_cell_volume                     2242.4(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker AXS Inc.)'
_computing_data_collection       'APEX2 2012.2 (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT v7.68A (Bruker AXS Inc.)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX Duo'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            59922
_diffrn_reflns_theta_full        29.69
_diffrn_reflns_theta_max         29.69
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9159
_exptl_absorpt_correction_T_min  0.8960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'translucent cube'
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         6325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0389P)²+1.0626P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                5746
_reflns_number_total             6325
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol401147w_si_004.cif
_cod_data_source_block           mo_cp197ppf2gontran_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1512106
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'
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
H10 H 0.5394 0.8742 0.1444 0.050 Uiso 1 1 d .
H9 H 0.5865 0.6144 0.0894 0.050 Uiso 1 1 d .
H11 H 0.3902 0.6429 0.1073 0.050 Uiso 1 1 d .
H18 H 0.3038 0.9162 0.0843 0.050 Uiso 1 1 d .
S1 S 0.739971(19) 0.76616(3) 0.107995(12) 0.01315(6) Uani 1 1 d .
Si2 Si 0.16415(2) 0.74838(3) 0.036766(14) 0.01493(7) Uani 1 1 d .
O25 O 0.51144(6) 0.78957(8) -0.05628(4) 0.01728(14) Uani 1 1 d .
O7 O 0.77094(6) 0.72395(9) 0.04601(4) 0.02068(16) Uani 1 1 d .
O24 O 0.38952(7) 0.62497(8) -0.02938(4) 0.02068(15) Uani 1 1 d .
C9 C 0.60031(8) 0.70055(10) 0.10873(5) 0.01459(17) Uani 1 1 d .
O8 O 0.74254(6) 0.91388(8) 0.12487(4) 0.01919(15) Uani 1 1 d .
O14 O 0.37998(8) 0.50945(8) 0.20846(4) 0.02705(18) Uani 1 1 d .
C10 C 0.52005(8) 0.78092(11) 0.12836(5) 0.01500(17) Uani 1 1 d .
C18 C 0.31620(8) 0.82551(10) 0.06468(5) 0.01326(17) Uani 1 1 d .
C1 C 0.83320(8) 0.67846(10) 0.17303(5) 0.01484(17) Uani 1 1 d .
N12 N 0.35205(7) 0.74395(8) 0.18219(4) 0.01372(15) Uani 1 1 d .
C26 C 0.57094(9) 0.68354(11) -0.08874(5) 0.01777(19) Uani 1 1 d .
H26A H 0.5161 0.6372 -0.1250 0.021 Uiso 1 1 calc R
H26B H 0.6058 0.6110 -0.0564 0.021 Uiso 1 1 calc R
C11 C 0.39428(8) 0.73637(10) 0.11912(5) 0.01294(17) Uani 1 1 d .
C20 C 0.15776(9) 0.55783(11) 0.05774(5) 0.01952(19) Uani 1 1 d .
H20A H 0.1875 0.5444 0.1053 0.029 Uiso 1 1 calc R
H20B H 0.2053 0.5038 0.0320 0.029 Uiso 1 1 calc R
H20C H 0.0772 0.5252 0.0469 0.029 Uiso 1 1 calc R
C23 C 0.42442(8) 0.74508(10) -0.02721(5) 0.01477(18) Uani 1 1 d .
C19 C 0.06501(9) 0.85313(13) 0.07975(7) 0.0262(2) Uani 1 1 d .
H19A H -0.0156 0.8252 0.0629 0.039 Uiso 1 1 calc R
H19B H 0.0743 0.9535 0.0711 0.039 Uiso 1 1 calc R
H19C H 0.0843 0.8356 0.1277 0.039 Uiso 1 1 calc R
C22 C 0.37809(8) 0.86629(10) 0.00735(5) 0.01574(18) Uani 1 1 d .
H22A H 0.3230 0.9200 -0.0260 0.019 Uiso 1 1 calc R
H22B H 0.4435 0.9297 0.0251 0.019 Uiso 1 1 calc R
C6 C 0.82510(9) 0.70833(12) 0.23853(5) 0.0202(2) Uani 1 1 d .
H6 H 0.7669 0.7702 0.2483 0.024 Uiso 1 1 calc R
C27 C 0.66408(10) 0.76056(12) -0.11626(6) 0.0227(2) Uani 1 1 d .
H27A H 0.6281 0.8317 -0.1482 0.034 Uiso 1 1 calc R
H27B H 0.7074 0.6935 -0.1386 0.034 Uiso 1 1 calc R
H27C H 0.7172 0.8065 -0.0798 0.034 Uiso 1 1 calc R
C15 C 0.32270(10) 0.67584(12) 0.28740(5) 0.0213(2) Uani 1 1 d .
H15A H 0.3911 0.6727 0.3240 0.026 Uiso 1 1 calc R
H15B H 0.2610 0.6151 0.2992 0.026 Uiso 1 1 calc R
C5 C 0.90398(10) 0.64573(13) 0.28950(6) 0.0257(2) Uani 1 1 d .
H5 H 0.8990 0.6635 0.3345 0.031 Uiso 1 1 calc R
C21 C 0.11463(11) 0.77103(14) -0.05491(6) 0.0278(2) Uani 1 1 d .
H21A H 0.1643 0.7154 -0.0786 0.042 Uiso 1 1 calc R
H21B H 0.1196 0.8705 -0.0665 0.042 Uiso 1 1 calc R
H21C H 0.0341 0.7390 -0.0676 0.042 Uiso 1 1 calc R
C17 C 0.33695(9) 0.87590(11) 0.21701(5) 0.01896(19) Uani 1 1 d .
H17A H 0.2863 0.9423 0.1876 0.023 Uiso 1 1 calc R
H17B H 0.4126 0.9216 0.2338 0.023 Uiso 1 1 calc R
C13 C 0.35468(9) 0.62923(11) 0.22254(5) 0.01717(18) Uani 1 1 d .
C16 C 0.27947(10) 0.82653(12) 0.27431(5) 0.0230(2) Uani 1 1 d .
H16A H 0.3036 0.8861 0.3142 0.028 Uiso 1 1 calc R
H16B H 0.1938 0.8292 0.2614 0.028 Uiso 1 1 calc R
C3 C 0.99638(10) 0.52799(14) 0.20942(7) 0.0297(3) Uani 1 1 d .
H3 H 1.0552 0.4670 0.1998 0.036 Uiso 1 1 calc R
C2 C 0.91677(9) 0.58764(12) 0.15752(6) 0.0225(2) Uani 1 1 d .
H2 H 0.9198 0.5665 0.1125 0.027 Uiso 1 1 calc R
C4 C 0.99002(10) 0.55725(14) 0.27476(6) 0.0288(3) Uani 1 1 d .
H4 H 1.0448 0.5167 0.3098 0.035 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O7 S1 O8 118.93(5)
O7 S1 C9 107.36(5)
O8 S1 C9 108.72(5)
O7 S1 C1 108.06(5)
O8 S1 C1 107.24(5)
C9 S1 C1 105.82(5)
C20 Si2 C21 108.93(5)
C20 Si2 C19 110.67(5)
C21 Si2 C19 107.90(6)
C20 Si2 C18 112.24(4)
C21 Si2 C18 110.62(5)
C19 Si2 C18 106.38(5)
C23 O25 C26 116.98(8)
C10 C9 S1 120.81(8)
C9 C10 C11 121.99(9)
C22 C18 C11 112.65(7)
C22 C18 Si2 114.50(7)
C11 C18 Si2 113.32(6)
C2 C1 C6 121.78(9)
C2 C1 S1 119.04(8)
C6 C1 S1 119.08(8)
C13 N12 C11 121.31(8)
C13 N12 C17 112.31(8)
C11 N12 C17 124.01(8)
O25 C26 C27 106.09(8)
N12 C11 C10 110.98(8)
N12 C11 C18 110.69(7)
C10 C11 C18 111.51(8)
O24 C23 O25 124.10(9)
O24 C23 C22 126.12(9)
O25 C23 C22 109.78(8)
C23 C22 C18 115.37(8)
C1 C6 C5 118.66(10)
C13 C15 C16 104.45(8)
C4 C5 C6 120.24(11)
N12 C17 C16 102.72(8)
O14 C13 N12 125.41(10)
O14 C13 C15 126.15(10)
N12 C13 C15 108.43(9)
C15 C16 C17 104.04(8)
C4 C3 C2 120.34(11)
C1 C2 C3 118.61(11)
C3 C4 C5 120.35(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O7 1.4411(8)
S1 O8 1.4452(8)
S1 C9 1.7553(10)
S1 C1 1.7657(10)
Si2 C20 1.8666(11)
Si2 C21 1.8703(12)
Si2 C19 1.8713(11)
Si2 C18 1.9136(10)
O25 C23 1.3425(12)
O25 C26 1.4556(12)
O24 C23 1.2110(12)
C9 C10 1.3316(13)
O14 C13 1.2247(13)
C10 C11 1.5119(13)
C18 C22 1.5408(13)
C18 C11 1.5545(13)
C1 C2 1.3870(14)
C1 C6 1.3915(14)
N12 C13 1.3649(13)
N12 C11 1.4690(12)
N12 C17 1.4699(13)
C26 C27 1.5092(14)
C23 C22 1.5061(14)
C6 C5 1.3917(15)
C15 C13 1.5125(14)
C15 C16 1.5266(16)
C5 C4 1.3897(18)
C17 C16 1.5323(14)
C3 C4 1.3822(19)
C3 C2 1.3965(16)
