#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/53/1505373.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_1505373
loop_
_publ_author_name
'Koo, Bonsuk'
'McDonald, Frank E.'
_publ_section_title
;
 Fischer carbene catalysis of alkynol cycloisomerization: application to
 the synthesis of the altromycin B disaccharide.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1737
_journal_page_last               1740
_journal_paper_doi               10.1021/ol070435s
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C16 H21 N O3 Si'
_chemical_formula_weight         303.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 101.346(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6408(8)
_cell_length_b                   6.0649(5)
_cell_length_c                   13.6002(10)
_cell_measurement_reflns_used    4023
_cell_measurement_temperature    446(2)
_cell_measurement_theta_max      65.27
_cell_measurement_theta_min      3.31
_cell_volume                     860.54(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      446(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6072
_diffrn_reflns_theta_full        65.71
_diffrn_reflns_theta_max         65.71
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    1.280
_exptl_absorpt_correction_T_max  0.9272
_exptl_absorpt_correction_T_min  0.6285
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.2007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0729
_reflns_number_gt                2314
_reflns_number_total             2403
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070435ssi20070220_045620.cif
_cod_data_source_block           bko4s
_cod_original_cell_volume        860.54(11)
_cod_database_code               1505373
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 0.55017(17) 0.7544(3) 0.14767(14) 0.0344(5) Uani 1 1 d .
C2 C 0.45088(17) 0.8835(3) 0.09632(13) 0.0310(4) Uani 1 1 d .
H2 H 0.4686 1.0019 0.0577 0.037 Uiso 1 1 calc R
C3 C 0.32491(17) 0.8357(3) 0.10267(13) 0.0302(4) Uani 1 1 d .
H3 H 0.2587 0.9225 0.0680 0.036 Uiso 1 1 calc R
C4 C 0.29667(16) 0.6597(3) 0.16022(12) 0.0284(4) Uani 1 1 d .
C5 C 0.39683(19) 0.5346(4) 0.21293(16) 0.0447(6) Uani 1 1 d .
H5 H 0.3797 0.4193 0.2534 0.054 Uiso 1 1 calc R
C6 C 0.52178(19) 0.5802(4) 0.20558(17) 0.0484(6) Uani 1 1 d .
H6 H 0.5879 0.4928 0.2400 0.058 Uiso 1 1 calc R
C7 C 0.05290(15) 0.6735(3) 0.11139(12) 0.0275(4) Uani 1 1 d .
C8 C -0.02159(17) 0.5464(3) 0.17853(13) 0.0292(4) Uani 1 1 d .
H8 H -0.0569 0.6479 0.2222 0.035 Uiso 1 1 calc R
C9 C 0.11426(17) 0.4575(3) 0.23343(12) 0.0281(4) Uani 1 1 d .
C10 C 0.13362(18) 0.2131(4) 0.21745(14) 0.0358(5) Uani 1 1 d .
H10A H 0.2210 0.1743 0.2445 0.054 Uiso 1 1 calc R
H10B H 0.1144 0.1809 0.1470 0.054 Uiso 1 1 calc R
H10C H 0.0777 0.1296 0.2507 0.054 Uiso 1 1 calc R
C11 C 0.15374(17) 0.5257(3) 0.33891(13) 0.0312(4) Uani 1 1 d .
C12 C 0.18660(19) 0.5846(4) 0.42420(15) 0.0387(5) Uani 1 1 d .
C13 C 0.70785(19) 0.9459(4) 0.07853(18) 0.0505(6) Uani 1 1 d .
H13A H 0.6601 0.9163 0.0123 0.076 Uiso 1 1 calc R
H13B H 0.7979 0.9402 0.0781 0.076 Uiso 1 1 calc R
H13C H 0.6861 1.0898 0.0994 0.076 Uiso 1 1 calc R
C14 C 0.4095(2) 0.5972(5) 0.59739(19) 0.0636(7) Uani 1 1 d .
H14A H 0.4138 0.4399 0.5907 0.095 Uiso 1 1 calc R
H14B H 0.4368 0.6371 0.6666 0.095 Uiso 1 1 calc R
H14C H 0.4646 0.6659 0.5583 0.095 Uiso 1 1 calc R
C15 C 0.2338(5) 0.9966(6) 0.5432(3) 0.158(3) Uani 1 1 d .
H15A H 0.2935 1.0484 0.5038 0.237 Uiso 1 1 calc R
H15B H 0.2548 1.0593 0.6092 0.237 Uiso 1 1 calc R
H15C H 0.1486 1.0401 0.5118 0.237 Uiso 1 1 calc R
C16 C 0.1368(3) 0.5873(8) 0.63307(18) 0.1002(15) Uani 1 1 d .
H16A H 0.0495 0.6228 0.6039 0.150 Uiso 1 1 calc R
H16B H 0.1596 0.6547 0.6980 0.150 Uiso 1 1 calc R
H16C H 0.1460 0.4303 0.6397 0.150 Uiso 1 1 calc R
N1 N 0.16844(13) 0.6074(3) 0.16455(10) 0.0288(4) Uani 1 1 d .
O1 O 0.67735(12) 0.7846(3) 0.14640(12) 0.0497(4) Uani 1 1 d .
O2 O 0.02361(12) 0.7902(2) 0.03711(9) 0.0334(3) Uani 1 1 d .
O3 O -0.11427(12) 0.3965(2) 0.13411(9) 0.0366(3) Uani 1 1 d .
H3A H -0.0921 0.3396 0.0855 0.055 Uiso 1 1 calc R
Si1 Si 0.24249(6) 0.69085(11) 0.55220(4) 0.04830(18) Uani 1 1 d .
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
O1 C1 C6 115.82(17)
O1 C1 C2 125.08(17)
C6 C1 C2 119.10(17)
C1 C2 C3 119.91(18)
C2 C3 C4 120.84(17)
C5 C4 C3 118.78(16)
C5 C4 N1 120.36(17)
C3 C4 N1 120.85(16)
C6 C5 C4 120.37(19)
C5 C6 C1 120.97(19)
O2 C7 N1 131.87(16)
O2 C7 C8 134.99(16)
N1 C7 C8 93.14(14)
O3 C8 C7 118.49(14)
O3 C8 C9 119.07(16)
C7 C8 C9 85.47(13)
C11 C9 N1 111.54(15)
C11 C9 C10 113.15(16)
N1 C9 C10 115.01(14)
C11 C9 C8 114.98(15)
N1 C9 C8 85.79(13)
C10 C9 C8 113.67(15)
C12 C11 C9 178.9(2)
C11 C12 Si1 176.16(19)
C7 N1 C4 133.78(15)
C7 N1 C9 95.29(13)
C4 N1 C9 130.92(15)
C1 O1 C13 116.84(15)
C16 Si1 C12 108.99(13)
C16 Si1 C14 110.98(14)
C12 Si1 C14 108.46(11)
C16 Si1 C15 110.7(2)
C12 Si1 C15 106.50(14)
C14 Si1 C15 111.09(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.369(2)
C1 C6 1.386(3)
C1 C2 1.388(3)
C2 C3 1.391(2)
C3 C4 1.391(3)
C4 C5 1.388(3)
C4 N1 1.413(2)
C5 C6 1.381(3)
C7 O2 1.223(2)
C7 N1 1.358(2)
C7 C8 1.530(3)
C8 O3 1.389(2)
C8 C9 1.585(2)
C9 C11 1.473(3)
C9 N1 1.500(2)
C9 C10 1.518(3)
C11 C12 1.198(3)
C12 Si1 1.842(2)
C13 O1 1.425(3)
C14 Si1 1.852(3)
C15 Si1 1.860(4)
C16 Si1 1.832(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
O3 H3A O2 0.82 1.97 2.7663(17) 163.6 2_545
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 179.46(19)
C6 C1 C2 C3 -0.6(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 1.2(3)
C2 C3 C4 N1 -178.29(17)
C3 C4 C5 C6 -2.0(3)
N1 C4 C5 C6 177.4(2)
C4 C5 C6 C1 1.6(4)
O1 C1 C6 C5 179.7(2)
C2 C1 C6 C5 -0.2(3)
O2 C7 C8 O3 54.5(3)
N1 C7 C8 O3 -124.98(17)
O2 C7 C8 C9 175.2(2)
N1 C7 C8 C9 -4.22(13)
O3 C8 C9 C11 -124.12(18)
C7 C8 C9 C11 115.65(17)
O3 C8 C9 N1 124.05(16)
C7 C8 C9 N1 3.82(12)
O3 C8 C9 C10 8.5(2)
C7 C8 C9 C10 -111.68(16)
N1 C9 C11 C12 12(11)
C10 C9 C11 C12 144(11)
C8 C9 C11 C12 -83(11)
C9 C11 C12 Si1 -9(13)
O2 C7 N1 C4 5.9(4)
C8 C7 N1 C4 -174.63(19)
O2 C7 N1 C9 -175.0(2)
C8 C7 N1 C9 4.46(14)
C5 C4 N1 C7 -168.0(2)
C3 C4 N1 C7 11.5(3)
C5 C4 N1 C9 13.2(3)
C3 C4 N1 C9 -167.36(17)
C11 C9 N1 C7 -119.54(17)
C10 C9 N1 C7 109.88(17)
C8 C9 N1 C7 -4.31(14)
C11 C9 N1 C4 59.6(2)
C10 C9 N1 C4 -71.0(2)
C8 C9 N1 C4 174.82(18)
C6 C1 O1 C13 172.9(2)
C2 C1 O1 C13 -7.2(3)
C11 C12 Si1 C16 156(3)
C11 C12 Si1 C14 -83(3)
C11 C12 Si1 C15 37(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199573 ChemSpider
