#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503180.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_1503180
loop_
_publ_author_name
'Matsuo, Jun-ichi'
'Kawano, Mizuki'
'Okuno, Ryosuke'
'Ishibashi, Hiroyuki'
_publ_section_title
;
 Titanium(IV) chloride-mediated carbon-carbon bond-forming reaction
 between 3,3-dialkylcyclobutanones and aldehydes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3960
_journal_page_last               3962
_journal_paper_doi               10.1021/ol101653b
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C20 H35 Cl O2 Si '
_chemical_formula_sum            'C20 H35 Cl O2 Si'
_chemical_formula_weight         371.03
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 109.09(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.956(6)
_cell_length_b                   20.04(1)
_cell_length_c                   11.392(7)
_cell_measurement_reflns_used    7026
_cell_measurement_temperature    123.2
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     2148(2)
_computing_cell_refinement       CRYSTALCLEAR
_computing_data_collection       CRYSTALCLEAR
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    DirectMethod
_diffrn_detector_area_resol_mean 14.46
_diffrn_measured_fraction_theta_full 0.9594
_diffrn_measured_fraction_theta_max 0.9594
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4896
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.12
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2601
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.0019
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00106|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0753
_reflns_number_gt                2601
_reflns_number_total             4772
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ol101653b_si_002.cif
_cod_data_source_block           '_matsuo11'
_cod_original_cell_volume        2147(2)
_cod_original_formula_sum        'C20 H35 Cl O2 Si '
_cod_database_code               1503180
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,-z
-x,-y,-z
1/2+x,1/2-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_calc_flag
Cl1 Cl 0.0578(1) 0.14689(6) 0.2243(1) 0.0322(3) Uani 1.00 d
Si1 Si 0.3030(1) 0.08130(6) 0.7141(1) 0.0217(3) Uani 1.00 d
O1 O 0.6254(3) 0.2135(2) 0.5229(3) 0.0267(9) Uani 1.00 d
O2 O 0.3594(3) 0.2638(1) 0.4620(3) 0.0238(8) Uani 1.00 d
C1 C 0.5862(4) 0.1493(2) 0.5558(4) 0.021(1) Uani 1.00 d
C2 C 0.6906(4) 0.1253(2) 0.6759(4) 0.023(1) Uani 1.00 d
C3 C 0.7430(5) 0.1691(2) 0.7746(4) 0.026(1) Uani 1.00 d
C4 C 0.8380(5) 0.1472(3) 0.8860(4) 0.036(1) Uani 1.00 d
C5 C 0.8825(5) 0.0814(3) 0.8995(5) 0.035(1) Uani 1.00 d
C6 C 0.8326(5) 0.0376(3) 0.8017(5) 0.034(1) Uani 1.00 d
C7 C 0.7377(5) 0.0605(2) 0.6921(4) 0.027(1) Uani 1.00 d
C8 C 0.4344(4) 0.1563(2) 0.5607(4) 0.020(1) Uani 1.00 d
C9 C 0.3728(4) 0.0875(2) 0.5801(4) 0.021(1) Uani 1.00 d
C10 C 0.4297(6) 0.1209(3) 0.8524(5) 0.036(2) Uani 1.00 d
C11 C 0.1284(5) 0.1249(3) 0.6736(5) 0.036(2) Uani 1.00 d
C12 C 0.2833(5) -0.0093(2) 0.7487(4) 0.024(1) Uani 1.00 d
C13 C 0.4242(5) -0.0444(2) 0.7742(4) 0.028(1) Uani 1.00 d
C14 C 0.2330(5) -0.0172(2) 0.8604(5) 0.033(1) Uani 1.00 d
C15 C 0.1742(5) -0.0437(3) 0.6364(5) 0.037(2) Uani 1.00 d
C16 C 0.3341(4) 0.1932(2) 0.4487(4) 0.021(1) Uani 1.00 d
C17 C 0.3411(4) 0.1688(2) 0.3242(4) 0.021(1) Uani 1.00 d
C18 C 0.2174(4) 0.1873(2) 0.2097(4) 0.023(1) Uani 1.00 d
C19 C 0.1852(5) 0.2613(3) 0.1930(5) 0.034(1) Uani 1.00 d
C20 C 0.2404(5) 0.1589(3) 0.0959(4) 0.031(1) Uani 1.00 d
H1 H 0.7250 0.2062 0.5210 0.0912 Uiso 1.00 calc
H2 H 0.5838 0.1171 0.4905 0.0267 Uiso 1.00 calc
H3 H 0.7117 0.2157 0.7649 0.0315 Uiso 1.00 calc
H4 H 0.8755 0.1783 0.9538 0.0452 Uiso 1.00 calc
H5 H 0.9455 0.0669 0.9791 0.0429 Uiso 1.00 calc
H6 H 0.8656 -0.0085 0.8105 0.0437 Uiso 1.00 calc
H7 H 0.7028 0.0309 0.6219 0.0339 Uiso 1.00 calc
H8 H 0.4432 0.1826 0.6343 0.0250 Uiso 1.00 calc
H9 H 0.4441 0.0549 0.5905 0.0279 Uiso 1.00 calc
H10 H 0.2954 0.0781 0.5057 0.0279 Uiso 1.00 calc
H11 H 0.4426 0.1670 0.8392 0.0433 Uiso 1.00 calc
H12 H 0.5217 0.0994 0.8746 0.0433 Uiso 1.00 calc
H13 H 0.3976 0.1170 0.9234 0.0433 Uiso 1.00 calc
H14 H 0.1381 0.1709 0.6546 0.0451 Uiso 1.00 calc
H15 H 0.0609 0.1048 0.6019 0.0451 Uiso 1.00 calc
H16 H 0.0911 0.1228 0.7406 0.0451 Uiso 1.00 calc
H17 H 0.4548 -0.0417 0.7029 0.0330 Uiso 1.00 calc
H18 H 0.4941 -0.0244 0.8429 0.0330 Uiso 1.00 calc
H19 H 0.4146 -0.0903 0.7920 0.0330 Uiso 1.00 calc
H20 H 0.2988 0.0018 0.9322 0.0425 Uiso 1.00 calc
H21 H 0.1428 0.0056 0.8440 0.0425 Uiso 1.00 calc
H22 H 0.2188 -0.0630 0.8745 0.0425 Uiso 1.00 calc
H23 H 0.1646 -0.0898 0.6541 0.0466 Uiso 1.00 calc
H24 H 0.0834 -0.0228 0.6176 0.0466 Uiso 1.00 calc
H25 H 0.2036 -0.0411 0.5644 0.0466 Uiso 1.00 calc
H26 H 0.2376 0.1861 0.4484 0.0283 Uiso 1.00 calc
H27 H 0.4605 0.2828 0.4966 0.0912 Uiso 1.00 calc
H28 H 0.4263 0.1861 0.3141 0.0228 Uiso 1.00 calc
H29 H 0.3486 0.1209 0.3276 0.0228 Uiso 1.00 calc
H30 H 0.1709 0.2805 0.2642 0.0440 Uiso 1.00 calc
H31 H 0.2632 0.2847 0.1780 0.0440 Uiso 1.00 calc
H32 H 0.1022 0.2688 0.1225 0.0440 Uiso 1.00 calc
H33 H 0.3253 0.1765 0.0860 0.0385 Uiso 1.00 calc
H34 H 0.1620 0.1707 0.0237 0.0385 Uiso 1.00 calc
H35 H 0.2474 0.1115 0.1004 0.0385 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Si Si 0.082 0.070
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
Cl Cl 0.148 0.159
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C9 Si1 C10 109.5(2) yes
C9 Si1 C11 109.3(2) yes
C9 Si1 C12 109.1(2) yes
C10 Si1 C11 109.4(2) yes
C10 Si1 C12 109.0(2) yes
C11 Si1 C12 110.6(2) yes
O1 C1 C2 111.1(3) yes
O1 C1 C8 106.5(3) yes
C2 C1 C8 113.1(3) yes
C1 C2 C3 120.1(4) yes
C1 C2 C7 122.0(4) yes
C3 C2 C7 117.9(4) yes
C2 C3 C4 120.4(4) yes
C3 C4 C5 120.1(5) yes
C4 C5 C6 120.0(4) yes
C5 C6 C7 118.7(5) yes
C2 C7 C6 122.8(5) yes
C1 C8 C9 111.3(3) yes
C1 C8 C16 113.2(3) yes
C9 C8 C16 111.6(3) yes
Si1 C9 C8 116.3(3) yes
Si1 C12 C13 109.6(3) yes
Si1 C12 C14 111.2(3) yes
Si1 C12 C15 110.5(3) yes
C13 C12 C14 109.2(4) yes
C13 C12 C15 108.0(4) yes
C14 C12 C15 108.2(4) yes
O2 C16 C8 110.1(3) yes
O2 C16 C17 110.8(3) yes
C8 C16 C17 113.9(3) yes
C16 C17 C18 116.8(4) yes
Cl1 C18 C17 107.3(3) yes
Cl1 C18 C19 106.8(3) yes
Cl1 C18 C20 106.9(3) yes
C17 C18 C19 115.2(4) yes
C17 C18 C20 109.9(4) yes
C19 C18 C20 110.4(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C18 1.839(4) yes
Si1 C9 1.876(4) yes
Si1 C10 1.845(5) yes
Si1 C11 1.864(5) yes
Si1 C12 1.881(5) yes
O1 C1 1.428(5) yes
O2 C16 1.435(5) yes
C1 C2 1.501(6) yes
C1 C8 1.537(6) yes
C2 C3 1.387(6) yes
C2 C7 1.373(6) yes
C3 C4 1.383(7) yes
C4 C5 1.384(8) yes
C5 C6 1.376(7) yes
C6 C7 1.375(6) yes
C8 C9 1.553(6) yes
C8 C16 1.530(6) yes
C12 C13 1.510(6) yes
C12 C14 1.520(7) yes
C12 C15 1.543(7) yes
C16 C17 1.523(6) yes
C17 C18 1.518(6) yes
C18 C19 1.516(7) yes
C18 C20 1.500(6) yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O1 O2 2.679(4) 4_555
O1 C16 3.111(5) 4_555
C5 C14 3.538(7) 3_657
