#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/52/7115246.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_7115246
loop_
_publ_author_name
'Knölker, Hans-Joachim'
'Schmitt, Oliver'
'Wanzl, Günter'
'Baum, Gerhard'
_publ_section_title
;
 Stereoselective total synthesis of (+-)-fragranol by TiCl4 promoted [2+2]
 cycloaddition of allyl-tert-butyldiphenylsilane and methyl
 methacrylate†
;
_journal_issue                   17
_journal_name_full               'Chemical Communications'
_journal_page_first              1737
_journal_paper_doi               10.1039/a905019a
_journal_year                    1999
_chemical_formula_sum            'C24 H32 O2 Si'
_chemical_formula_weight         380.59
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.900(3)
_cell_length_b                   14.751(5)
_cell_length_c                   18.956(6)
_cell_measurement_temperature    200(2)
_cell_volume                     2209.0(13)
_computing_cell_refinement       'STOE IPDS software'
_computing_data_collection       'STOE IPDS software'
_computing_data_reduction        'STOE IPDS software'
_computing_molecular_graphics    'SCHAKAL-97 (Keller Freiburg 1997'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Area detector (IPDS, STOE)'
_diffrn_measurement_method       'Image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10267
_diffrn_reflns_theta_full        25.82
_diffrn_reflns_theta_max         25.82
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.121
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0523
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0974P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                3964
_reflns_number_total             4228
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            905019a.txt
_cod_data_source_block           anti-5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7115246
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_calc_flag
_atom_site_refinement_flags
C1 C 0.2385(3) 0.05168(17) 0.64179(11) 0.0374(5) Uani 1 d .
C2 C 0.1727(3) 0.04830(15) 0.71990(10) 0.0309(4) Uani 1 d .
H2 H 0.2568 0.0156 0.7500 0.037 Uiso 1 calc R
C3 C 0.2040(3) 0.15104(17) 0.72472(12) 0.0415(5) Uani 1 d .
H3A H 0.0998 0.1878 0.7199 0.050 Uiso 1 calc R
H3B H 0.2693 0.1694 0.7670 0.050 Uiso 1 calc R
C4 C 0.3103(5) 0.1468(2) 0.65720(15) 0.0623(9) Uani 1 d .
H4A H 0.4338 0.1474 0.6658 0.075 Uiso 1 calc R
H4B H 0.2784 0.1929 0.6216 0.075 Uiso 1 calc R
C5 C 0.3741(3) -0.0166(2) 0.62446(11) 0.0449(6) Uani 1 d .
O1 O 0.5091(3) 0.00036(19) 0.59973(14) 0.0787(7) Uani 1 d .
O2 O 0.3253(3) -0.10089(13) 0.64044(11) 0.0531(5) Uani 1 d .
C6 C 0.4476(5) -0.1713(3) 0.6266(2) 0.0752(10) Uani 1 d .
H6A H 0.4888 -0.1658 0.5781 0.113 Uiso 1 calc R
H6B H 0.3943 -0.2307 0.6331 0.113 Uiso 1 calc R
H6C H 0.5428 -0.1652 0.6594 0.113 Uiso 1 calc R
C7 C 0.1018(4) 0.0488(2) 0.58572(11) 0.0461(6) Uani 1 d .
H7A H 0.1516 0.0625 0.5396 0.069 Uiso 1 calc R
H7B H 0.0144 0.0938 0.5967 0.069 Uiso 1 calc R
H7C H 0.0509 -0.0118 0.5846 0.069 Uiso 1 calc R
C8 C -0.0046(3) 0.01253(15) 0.73531(10) 0.0306(4) Uani 1 d .
H8A H -0.0207 -0.0454 0.7098 0.037 Uiso 1 calc R
H8B H -0.0887 0.0563 0.7169 0.037 Uiso 1 calc R
Si Si -0.04697(7) -0.00675(4) 0.83190(2) 0.02648(17) Uani 1 d .
C9 C -0.2831(3) -0.02710(17) 0.84590(12) 0.0380(5) Uani 1 d .
C10 C -0.3381(4) -0.1022(3) 0.7959(2) 0.0741(10) Uani 1 d .
H10A H -0.4590 -0.1144 0.8025 0.111 Uiso 1 calc R
H10B H -0.2731 -0.1573 0.8059 0.111 Uiso 1 calc R
H10C H -0.3177 -0.0832 0.7471 0.111 Uiso 1 calc R
C11 C -0.3220(4) -0.0555(4) 0.92139(18) 0.0909(14) Uani 1 d .
H11A H -0.2974 -0.0051 0.9534 0.136 Uiso 1 calc R
H11B H -0.2517 -0.1078 0.9341 0.136 Uiso 1 calc R
H11C H -0.4418 -0.0720 0.9253 0.136 Uiso 1 calc R
C12 C -0.3880(4) 0.0563(2) 0.8282(2) 0.0681(9) Uani 1 d .
H12A H -0.5086 0.0410 0.8307 0.102 Uiso 1 calc R
H12B H -0.3604 0.0769 0.7804 0.102 Uiso 1 calc R
H12C H -0.3628 0.1046 0.8620 0.102 Uiso 1 calc R
C13 C 0.0734(3) -0.11009(14) 0.86036(10) 0.0298(4) Uani 1 d .
C14 C 0.1580(3) -0.16555(15) 0.81184(11) 0.0345(5) Uani 1 d .
H14 H 0.1565 -0.1494 0.7633 0.041 Uiso 1 calc R
C15 C 0.2434(3) -0.24295(16) 0.83206(15) 0.0419(5) Uani 1 d .
H15 H 0.2996 -0.2787 0.7975 0.050 Uiso 1 calc R
C16 C 0.2481(3) -0.26901(17) 0.90217(16) 0.0460(6) Uani 1 d .
H16 H 0.3066 -0.3223 0.9162 0.055 Uiso 1 calc R
C17 C 0.1662(4) -0.21595(18) 0.95113(13) 0.0490(6) Uani 1 d .
H17 H 0.1682 -0.2332 0.9994 0.059 Uiso 1 calc R
C18 C 0.0814(3) -0.13837(17) 0.93163(11) 0.0405(5) Uani 1 d .
H18 H 0.0269 -0.1030 0.9668 0.049 Uiso 1 calc R
C19 C 0.0350(3) 0.09531(15) 0.88094(9) 0.0313(4) Uani 1 d .
C20 C 0.1758(3) 0.09041(18) 0.92528(12) 0.0414(5) Uani 1 d .
H20 H 0.2258 0.0331 0.9347 0.050 Uiso 1 calc R
C21 C 0.2438(4) 0.1676(2) 0.95586(14) 0.0558(7) Uani 1 d .
H21 H 0.3403 0.1627 0.9855 0.067 Uiso 1 calc R
C22 C 0.1725(4) 0.2513(2) 0.94353(15) 0.0564(8) Uani 1 d .
H22 H 0.2187 0.3038 0.9652 0.068 Uiso 1 calc R
C23 C 0.0345(4) 0.25861(17) 0.89988(14) 0.0500(6) Uani 1 d .
H23 H -0.0150 0.3162 0.8910 0.060 Uiso 1 calc R
C24 C -0.0325(3) 0.18111(16) 0.86870(13) 0.0409(5) Uani 1 d .
H24 H -0.1272 0.1869 0.8381 0.049 Uiso 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'
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
C5 C1 C7 109.6(2)
C5 C1 C4 112.9(2)
C7 C1 C4 114.9(2)
C5 C1 C2 114.8(2)
C7 C1 C2 115.10(19)
C4 C1 C2 88.40(17)
C8 C2 C3 118.5(2)
C8 C2 C1 119.72(18)
C3 C2 C1 88.37(17)
C4 C3 C2 89.91(18)
C3 C4 C1 89.65(19)
O1 C5 O2 122.9(3)
O1 C5 C1 125.6(3)
O2 C5 C1 111.5(2)
C5 O2 C6 115.8(3)
C2 C8 Si 113.67(14)
C13 Si C8 108.20(9)
C13 Si C19 109.46(9)
C8 Si C19 107.34(9)
C13 Si C9 109.14(10)
C8 Si C9 109.43(10)
C19 Si C9 113.15(10)
C12 C9 C10 107.2(3)
C12 C9 C11 108.7(3)
C10 C9 C11 109.1(3)
C12 C9 Si 112.03(17)
C10 C9 Si 107.88(18)
C11 C9 Si 111.8(2)
C14 C13 C18 115.7(2)
C14 C13 Si 121.85(16)
C18 C13 Si 122.45(17)
C15 C14 C13 122.3(2)
C14 C15 C16 120.6(2)
C17 C16 C15 118.5(2)
C16 C17 C18 121.4(2)
C17 C18 C13 121.5(2)
C24 C19 C20 116.9(2)
C24 C19 Si 120.80(17)
C20 C19 Si 121.98(18)
C21 C20 C19 121.2(3)
C22 C21 C20 120.5(3)
C23 C22 C21 119.9(2)
C22 C23 C24 119.5(3)
C23 C24 C19 122.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C5 1.507(4)
C1 C7 1.516(4)
C1 C4 1.541(4)
C1 C2 1.570(3)
C2 C8 1.525(3)
C2 C3 1.538(3)
C3 C4 1.532(3)
C5 O1 1.191(3)
C5 O2 1.336(4)
O2 C6 1.442(4)
C8 Si 1.883(2)
Si C13 1.876(2)
Si C19 1.884(2)
Si C9 1.908(2)
C9 C12 1.521(4)
C9 C10 1.521(4)
C9 C11 1.522(4)
C13 C14 1.401(3)
C13 C18 1.415(3)
C14 C15 1.381(3)
C15 C16 1.384(4)
C16 C17 1.376(4)
C17 C18 1.377(4)
C19 C24 1.393(3)
C19 C20 1.396(3)
C20 C21 1.386(4)
C21 C22 1.376(5)
C22 C23 1.373(5)
C23 C24 1.392(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11036294
