#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/49/1504925.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_1504925
loop_
_publ_author_name
'Glass, Adam C.'
'Morris, Benjamin B.'
'Zakharov, Lev N.'
'Liu, Shih-Yuan'
_publ_section_title
;
 Synthesis of substituted naphthalenes via a catalytic ring-expansion
 rearrangement.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4855
_journal_page_last               4857
_journal_paper_doi               10.1021/ol8019617
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C13 H16 O Si'
_chemical_formula_weight         216.35
_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           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 108.965(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5789(12)
_cell_length_b                   12.6743(16)
_cell_length_c                   10.9538(14)
_cell_measurement_reflns_used    3850
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.25
_cell_volume                     1257.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13877
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0557P)²+0.2893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                2342
_reflns_number_total             2744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8019617_si_003.cif
_cod_data_source_block           liu15
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1504925
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
Si1 Si 0.06666(4) 0.17708(3) 0.21956(3) 0.02789(13) Uani 1 1 d
O1 O 0.24159(13) -0.12500(8) 0.53647(11) 0.0422(3) Uani 1 1 d
C1 C 0.17327(15) 0.12451(10) 0.38302(13) 0.0264(3) Uani 1 1 d
C2 C 0.34076(15) 0.12152(11) 0.42575(14) 0.0285(3) Uani 1 1 d
C3 C 0.25628(15) 0.01955(11) 0.39583(13) 0.0281(3) Uani 1 1 d
C4 C 0.28434(15) -0.03732(11) 0.52134(13) 0.0289(3) Uani 1 1 d
C5 C 0.38041(14) 0.03258(10) 0.62421(13) 0.0275(3) Uani 1 1 d
C6 C 0.41627(14) 0.12237(10) 0.56801(14) 0.0285(3) Uani 1 1 d
C7 C 0.51042(17) 0.19680(12) 0.64509(17) 0.0374(4) Uani 1 1 d
C8 C 0.56689(18) 0.17949(13) 0.77699(17) 0.0420(4) Uani 1 1 d
C9 C 0.53023(17) 0.08974(13) 0.83213(16) 0.0397(4) Uani 1 1 d
C10 C 0.43560(16) 0.01459(13) 0.75625(14) 0.0336(3) Uani 1 1 d
C11 C 0.0773(2) 0.32330(13) 0.22668(17) 0.0416(4) Uani 1 1 d
C12 C -0.12851(19) 0.13348(16) 0.1752(2) 0.0451(4) Uani 1 1 d
C13 C 0.1516(2) 0.12677(17) 0.10039(18) 0.0478(4) Uani 1 1 d
H1 H 0.1337(18) 0.1397(12) 0.4548(16) 0.032(4) Uiso 1 1 d
H2 H 0.3891(18) 0.1483(13) 0.3680(16) 0.034(4) Uiso 1 1 d
H3 H 0.2477(17) -0.0202(13) 0.3224(16) 0.033(4) Uiso 1 1 d
H7 H 0.5384(19) 0.2572(14) 0.6059(17) 0.041(5) Uiso 1 1 d
H8 H 0.630(2) 0.2303(14) 0.8300(18) 0.044(5) Uiso 1 1 d
H9 H 0.5743(19) 0.0770(13) 0.9207(18) 0.042(5) Uiso 1 1 d
H10 H 0.4111(18) -0.0498(14) 0.7963(16) 0.038(4) Uiso 1 1 d
H11A H 0.173(3) 0.3470(18) 0.252(2) 0.076(7) Uiso 1 1 d
H11B H 0.032(2) 0.3521(16) 0.145(2) 0.062(6) Uiso 1 1 d
H11C H 0.031(2) 0.3481(16) 0.286(2) 0.055(6) Uiso 1 1 d
H12A H -0.186(3) 0.1667(17) 0.106(2) 0.070(7) Uiso 1 1 d
H12B H -0.167(3) 0.1557(19) 0.244(3) 0.086(8) Uiso 1 1 d
H12C H -0.143(3) 0.057(2) 0.159(2) 0.081(7) Uiso 1 1 d
H13A H 0.254(3) 0.146(2) 0.124(3) 0.098(9) Uiso 1 1 d
H13B H 0.103(3) 0.1551(18) 0.022(3) 0.079(7) Uiso 1 1 d
H13C H 0.146(2) 0.0511(18) 0.094(2) 0.062(6) Uiso 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 0.0033 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
C11 Si1 C12 110.19(9)
C11 Si1 C13 109.93(9)
C12 Si1 C13 110.32(10)
C11 Si1 C1 108.04(7)
C12 Si1 C1 109.54(8)
C13 Si1 C1 108.78(8)
C2 C1 C3 59.03(9)
C2 C1 Si1 119.80(10)
C3 C1 Si1 120.13(10)
C2 C1 H1 113.4(9)
C3 C1 H1 114.5(9)
Si1 C1 H1 117.2(9)
C6 C2 C3 106.15(12)
C6 C2 C1 115.30(12)
C3 C2 C1 60.95(9)
C6 C2 H2 120.9(10)
C3 C2 H2 120.1(10)
C1 C2 H2 118.4(10)
C4 C3 C2 106.88(11)
C4 C3 C1 115.78(12)
C2 C3 C1 60.02(9)
C4 C3 H3 118.2(10)
C2 C3 H3 123.0(10)
C1 C3 H3 119.6(10)
O1 C4 C5 126.35(13)
O1 C4 C3 126.74(13)
C5 C4 C3 106.87(12)
C6 C5 C10 122.08(13)
C6 C5 C4 109.41(12)
C10 C5 C4 128.45(13)
C7 C6 C5 119.56(14)
C7 C6 C2 129.85(14)
C5 C6 C2 110.59(12)
C6 C7 C8 118.92(15)
C6 C7 H7 119.5(11)
C8 C7 H7 121.5(11)
C9 C8 C7 121.07(15)
C9 C8 H8 119.7(11)
C7 C8 H8 119.3(11)
C8 C9 C10 120.70(15)
C8 C9 H9 120.0(11)
C10 C9 H9 119.2(11)
C5 C10 C9 117.67(15)
C5 C10 H10 122.1(10)
C9 C10 H10 120.2(10)
Si1 C11 H11A 112.1(14)
Si1 C11 H11B 110.4(13)
H11A C11 H11B 106(2)
Si1 C11 H11C 109.0(12)
H11A C11 H11C 109(2)
H11B C11 H11C 110.5(18)
Si1 C12 H12A 112.1(15)
Si1 C12 H12B 108.1(15)
H12A C12 H12B 104(2)
Si1 C12 H12C 114.1(14)
H12A C12 H12C 108(2)
H12B C12 H12C 111(2)
Si1 C13 H13A 111.3(17)
Si1 C13 H13B 108.8(16)
H13A C13 H13B 109(2)
Si1 C13 H13C 111.4(13)
H13A C13 H13C 107(2)
H13B C13 H13C 109.0(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C11 1.8564(17)
Si1 C12 1.8564(17)
Si1 C13 1.8611(18)
Si1 C1 1.8719(14)
O1 C4 1.2141(17)
C1 C2 1.5188(19)
C1 C3 1.5328(18)
C1 H1 0.996(16)
C2 C6 1.490(2)
C2 C3 1.5034(19)
C2 H2 0.959(18)
C3 C4 1.4972(19)
C3 H3 0.930(16)
C4 C5 1.4925(18)
C5 C6 1.389(2)
C5 C10 1.388(2)
C6 C7 1.386(2)
C7 C8 1.386(3)
C7 H7 0.957(18)
C8 C9 1.386(3)
C8 H8 0.943(19)
C9 C10 1.389(2)
C9 H9 0.937(18)
C10 H10 0.990(18)
C11 H11A 0.92(3)
C11 H11B 0.93(2)
C11 H11C 0.96(2)
C12 H12A 0.88(2)
C12 H12B 0.98(3)
C12 H12C 0.99(3)
C13 H13A 0.96(3)
C13 H13B 0.91(3)
C13 H13C 0.96(2)
