#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/59/1505972.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_1505972
loop_
_publ_author_name
'Romero, Antonio'
'Woerpel, K. A.'
_publ_section_title
;
 Stereoselective synthesis of highly substituted gamma-lactams by the
 [3+2] annulation of alpha-siloxy allylic silanes with chlorosulfonyl
 isocyanate.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2127
_journal_page_last               2130
_journal_paper_doi               10.1021/ol060596g
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C18 H29 N O Si'
_chemical_formula_weight         303.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.358(5)
_cell_angle_beta                 83.355(5)
_cell_angle_gamma                63.325(4)
_cell_formula_units_Z            2
_cell_length_a                   8.194(2)
_cell_length_b                   8.643(3)
_cell_length_c                   14.789(4)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    168(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.26
_cell_volume                     905.5(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      168(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '25s frmes at 0.3 deg omega increments'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9730
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  .73
_exptl_absorpt_correction_type   'semi-empirical from equivalents'
_exptl_absorpt_process_details   'computed via SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.28
_refine_diff_density_max         3.359
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.1111
_refine_ls_shift/su_max          0.086
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.11P)²+5.4P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3022
_refine_ls_wR_factor_ref         0.3092
_reflns_number_gt                3677
_reflns_number_total             4348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060596gsi20060311_041638.cif
_cod_data_source_block           kaw83
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1505972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Si1 Si 0.17007(15) 0.27454(14) 0.33310(8) 0.0170(3) Uani 1 1 d .
O1 O 0.6576(6) -0.0959(6) 0.1061(3) 0.0553(12) Uani 1 1 d .
N1 N 0.3544(9) 0.1259(7) 0.0837(3) 0.0491(14) Uani 1 1 d .
H1 H 0.3426 0.1274 0.0264 0.059 Uiso 1 1 calc R
C1 C 0.2644(7) 0.1383(6) 0.2399(3) 0.0252(9) Uani 1 1 d .
C2 C 0.2023(8) 0.2448(7) 0.1377(3) 0.0360(12) Uani 1 1 d .
H2 H 0.2099 0.3580 0.1275 0.043 Uiso 1 1 calc R
C3 C 0.5021(9) 0.0227(7) 0.1297(4) 0.0404(13) Uani 1 1 d .
C4 C 0.4757(8) 0.0591(7) 0.2271(4) 0.0372(12) Uani 1 1 d .
H4 H 0.5118 0.1539 0.2246 0.045 Uiso 1 1 calc R
C5 C 0.2066(9) -0.0145(7) 0.2663(4) 0.0394(13) Uani 1 1 d .
H5A H 0.2442 -0.0795 0.3292 0.059 Uiso 1 1 calc R
H5B H 0.2634 -0.0928 0.2244 0.059 Uiso 1 1 calc R
H5C H 0.0763 0.0336 0.2619 0.059 Uiso 1 1 calc R
C6 C 0.0199(11) 0.2812(11) 0.1073(5) 0.0598(19) Uani 1 1 d .
H6A H 0.0001 0.3470 0.0434 0.090 Uiso 1 1 calc R
H6B H -0.0725 0.3494 0.1461 0.090 Uiso 1 1 calc R
H6C H 0.0141 0.1708 0.1124 0.090 Uiso 1 1 calc R
C7 C 0.5977(9) -0.1037(8) 0.2995(6) 0.061(2) Uani 1 1 d .
H7A H 0.5770 -0.0754 0.3598 0.091 Uiso 1 1 calc R
H7B H 0.7235 -0.1367 0.2822 0.091 Uiso 1 1 calc R
H7C H 0.5689 -0.2007 0.3019 0.091 Uiso 1 1 calc R
C8 C 0.2113(7) 0.1184(6) 0.4517(3) 0.0299(10) Uani 1 1 d .
H8A H 0.3403 0.0498 0.4621 0.045 Uiso 1 1 calc R
H8B H 0.1560 0.0401 0.4546 0.045 Uiso 1 1 calc R
H8C H 0.1586 0.1857 0.4989 0.045 Uiso 1 1 calc R
C9 C -0.0841(6) 0.3967(6) 0.3239(4) 0.0282(9) Uani 1 1 d .
H9A H -0.1171 0.4802 0.2646 0.042 Uiso 1 1 calc R
H9B H -0.1317 0.4590 0.3733 0.042 Uiso 1 1 calc R
H9C H -0.1343 0.3135 0.3289 0.042 Uiso 1 1 calc R
C10 C 0.2753(5) 0.4341(5) 0.3341(3) 0.0188(8) Uani 1 1 d .
C11 C 0.2837(6) 0.5404(5) 0.2356(3) 0.0188(8) Uani 1 1 d .
C12 C 0.4478(6) 0.5191(6) 0.1889(3) 0.0267(9) Uani 1 1 d .
H12 H 0.5574 0.4374 0.2188 0.032 Uiso 1 1 calc R
C13 C 0.4515(7) 0.6173(7) 0.0986(4) 0.0353(11) Uani 1 1 d .
H13 H 0.5628 0.6007 0.0690 0.042 Uiso 1 1 calc R
C14 C 0.2894(8) 0.7398(7) 0.0527(3) 0.0345(11) Uani 1 1 d .
H14 H 0.2916 0.8056 -0.0074 0.041 Uiso 1 1 calc R
C15 C 0.1250(7) 0.7633(6) 0.0971(3) 0.0303(10) Uani 1 1 d .
H15 H 0.0158 0.8449 0.0668 0.036 Uiso 1 1 calc R
C16 C 0.1227(6) 0.6653(5) 0.1867(3) 0.0229(8) Uani 1 1 d .
H16 H 0.0108 0.6827 0.2156 0.028 Uiso 1 1 calc R
C17 C 0.1528(7) 0.5630(6) 0.3956(3) 0.0276(9) Uani 1 1 d .
H17A H 0.1471 0.4967 0.4577 0.041 Uiso 1 1 calc R
H17B H 0.0321 0.6294 0.3697 0.041 Uiso 1 1 calc R
H17C H 0.2027 0.6434 0.3978 0.041 Uiso 1 1 calc R
C18 C 0.4633(6) 0.3297(7) 0.3812(3) 0.0292(10) Uani 1 1 d .
H18A H 0.4516 0.2653 0.4428 0.044 Uiso 1 1 calc R
H18B H 0.5110 0.4109 0.3853 0.044 Uiso 1 1 calc R
H18C H 0.5450 0.2478 0.3449 0.044 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'
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
C9 Si1 C8 104.1(2)
C9 Si1 C1 109.7(2)
C8 Si1 C1 108.9(2)
C9 Si1 C10 110.9(2)
C8 Si1 C10 107.2(2)
C1 Si1 C10 115.32(19)
C3 N1 C2 114.9(5)
C5 C1 C2 109.5(4)
C5 C1 C4 109.1(4)
C2 C1 C4 100.2(4)
C5 C1 Si1 107.7(3)
C2 C1 Si1 115.2(3)
C4 C1 Si1 114.9(3)
C6 C2 N1 111.8(5)
C6 C2 C1 118.5(5)
N1 C2 C1 100.1(4)
N1 C3 O1 131.5(5)
N1 C3 C4 108.2(5)
O1 C3 C4 120.2(6)
C3 C4 C1 102.7(5)
C3 C4 C7 112.0(5)
C1 C4 C7 119.2(5)
C11 C10 C18 112.3(3)
C11 C10 C17 109.2(3)
C18 C10 C17 106.5(4)
C11 C10 Si1 111.0(3)
C18 C10 Si1 110.0(3)
C17 C10 Si1 107.7(3)
C12 C11 C16 116.5(4)
C12 C11 C10 122.8(4)
C16 C11 C10 120.7(4)
C11 C12 C13 121.6(4)
C14 C13 C12 120.1(5)
C15 C14 C13 119.5(5)
C14 C15 C16 119.9(4)
C15 C16 C11 122.3(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C9 1.868(5)
Si1 C8 1.882(5)
Si1 C1 1.908(4)
Si1 C10 1.930(4)
O1 C3 1.304(7)
N1 C3 1.279(9)
N1 C2 1.511(7)
C1 C5 1.543(6)
C1 C2 1.562(7)
C1 C4 1.558(7)
C2 C6 1.483(9)
C3 C4 1.523(7)
C4 C7 1.532(9)
C10 C11 1.526(6)
C10 C18 1.535(6)
C10 C17 1.541(6)
C11 C12 1.395(6)
C11 C16 1.405(6)
C12 C13 1.396(7)
C13 C14 1.388(8)
C14 C15 1.380(7)
C15 C16 1.383(6)
