#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154541.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_7154541
loop_
_publ_author_name
'Rasheed, O. K.'
'Hardcastle, I. R.'
'Raftery, J.'
'Quayle, P.'
_publ_section_title
;
 Aryne generation vs. Truce-Smiles and fries rearrangements during the
 Kobayashi fragmentation reaction: a new bi-aryl synthesis.
;
_journal_issue                   29
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8048
_journal_page_last               8052
_journal_paper_doi               10.1039/c5ob01239b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C14 H16 N2 O5 S Si'
_chemical_formula_weight         352.44
_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           SHELXL-97
_audit_update_record
;
2015-03-30 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.8790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2148(2)
_cell_length_b                   10.9938(2)
_cell_length_c                   12.0527(2)
_cell_measurement_reflns_used    9042
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.16
_cell_measurement_theta_min      3.60
_cell_volume                     1624.91(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15650
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         72.15
_diffrn_reflns_theta_min         3.60
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  0.6695
_exptl_absorpt_correction_T_min  0.553297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.5935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                2930
_reflns_number_total             3176
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01239b2.cif
_cod_data_source_block           s3883ma
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154537--7154542.cif.
;
_cod_original_cell_volume        1624.90(5)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154541
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
_atom_site_refinement_flags
C1 C 1.06569(14) 0.27306(16) 1.31857(14) 0.0333(3) Uani 1 1 d .
H1A H 1.1347 0.2281 1.3452 0.050 Uiso 1 1 calc R
H1B H 1.0132 0.2298 1.3440 0.050 Uiso 1 1 calc R
H1C H 1.0782 0.3547 1.3538 0.050 Uiso 1 1 calc R
C2 C 0.99433(12) 0.13015(13) 1.08706(14) 0.0269(3) Uani 1 1 d .
H2A H 0.9520 0.1343 1.0009 0.040 Uiso 1 1 calc R
H2B H 0.9562 0.0785 1.1252 0.040 Uiso 1 1 calc R
H2C H 1.0664 0.0957 1.1009 0.040 Uiso 1 1 calc R
C3 C 1.10184(12) 0.38372(14) 1.10455(14) 0.0276(3) Uani 1 1 d .
H3A H 1.1720 0.3426 1.1228 0.041 Uiso 1 1 calc R
H3B H 1.1135 0.4613 1.1476 0.041 Uiso 1 1 calc R
H3C H 1.0682 0.3988 1.0183 0.041 Uiso 1 1 calc R
C4 C 0.87076(11) 0.35718(12) 1.10459(12) 0.0196(3) Uani 1 1 d .
C5 C 0.80076(11) 0.35047(11) 0.97868(12) 0.0181(3) Uani 1 1 d .
C6 C 0.65888(12) 0.45423(14) 1.03208(14) 0.0278(3) Uani 1 1 d .
H6 H 0.5879 0.4887 1.0067 0.033 Uiso 1 1 calc R
C7 C 0.72719(13) 0.46662(14) 1.14578(14) 0.0305(3) Uani 1 1 d .
H7 H 0.7056 0.5104 1.2012 0.037 Uiso 1 1 calc R
C8 C 0.83276(12) 0.41317(13) 1.18248(13) 0.0251(3) Uani 1 1 d .
H8 H 0.8787 0.4166 1.2646 0.030 Uiso 1 1 calc R
C9 C 0.62654(10) 0.43994(12) 0.70992(12) 0.0204(3) Uani 1 1 d .
C10 C 0.59350(12) 0.56075(13) 0.69596(13) 0.0261(3) Uani 1 1 d .
H10 H 0.5586 0.5951 0.7447 0.031 Uiso 1 1 calc R
C11 C 0.61238(13) 0.63021(14) 0.60987(14) 0.0276(3) Uani 1 1 d .
H11 H 0.5914 0.7133 0.5987 0.033 Uiso 1 1 calc R
C12 C 0.66240(11) 0.57562(13) 0.54068(12) 0.0232(3) Uani 1 1 d .
C13 C 0.69559(12) 0.45538(14) 0.55366(13) 0.0269(3) Uani 1 1 d .
H13 H 0.7298 0.4211 0.5042 0.032 Uiso 1 1 calc R
C14 C 0.67763(12) 0.38636(13) 0.64050(13) 0.0260(3) Uani 1 1 d .
H14 H 0.6999 0.3037 0.6524 0.031 Uiso 1 1 calc R
N1 N 0.69129(9) 0.39111(10) 0.95080(10) 0.0208(2) Uani 1 1 d .
N2 N 0.68155(11) 0.65015(12) 0.44819(11) 0.0294(3) Uani 1 1 d .
O1 O 0.82686(8) 0.31140(9) 0.89842(8) 0.0228(2) Uani 1 1 d .
O2 O 0.60870(9) 0.22655(9) 0.79679(10) 0.0299(2) Uani 1 1 d .
O3 O 0.49524(8) 0.39589(11) 0.81973(10) 0.0327(3) Uani 1 1 d .
O4 O 0.73680(10) 0.60634(12) 0.39643(10) 0.0380(3) Uani 1 1 d .
O5 O 0.64149(12) 0.75162(12) 0.42897(12) 0.0450(3) Uani 1 1 d .
S1 S 0.59573(3) 0.35218(3) 0.81561(3) 0.02270(11) Uani 1 1 d .
Si1 Si 1.01031(3) 0.28570(3) 1.15196(3) 0.01942(11) 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'
S S 0.3331 0.5567 '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
Si1 C1 H1A 109.5
Si1 C1 H1B 109.5
H1A C1 H1B 109.5
Si1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
Si1 C2 H2A 109.5
Si1 C2 H2B 109.5
H2A C2 H2B 109.5
Si1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
Si1 C3 H3A 109.5
Si1 C3 H3B 109.5
H3A C3 H3B 109.5
Si1 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C8 C4 C5 119.09(13)
C8 C4 Si1 123.24(11)
C5 C4 Si1 117.66(10)
O1 C5 N1 118.96(12)
O1 C5 C4 125.95(12)
N1 C5 C4 115.07(11)
C7 C6 N1 120.31(13)
C7 C6 H6 119.8
N1 C6 H6 119.8
C6 C7 C8 119.02(13)
C6 C7 H7 120.5
C8 C7 H7 120.5
C4 C8 C7 122.78(14)
C4 C8 H8 118.6
C7 C8 H8 118.6
C14 C9 C10 122.33(13)
C14 C9 S1 119.93(11)
C10 C9 S1 117.67(11)
C11 C10 C9 118.83(13)
C11 C10 H10 120.6
C9 C10 H10 120.6
C12 C11 C10 118.30(13)
C12 C11 H11 120.8
C10 C11 H11 120.8
C11 C12 C13 123.40(14)
C11 C12 N2 118.02(13)
C13 C12 N2 118.58(13)
C14 C13 C12 118.25(13)
C14 C13 H13 120.9
C12 C13 H13 120.9
C13 C14 C9 118.88(13)
C13 C14 H14 120.6
C9 C14 H14 120.6
C6 N1 C5 122.70(12)
C6 N1 S1 119.07(10)
C5 N1 S1 118.11(9)
O5 N2 O4 124.28(14)
O5 N2 C12 117.76(13)
O4 N2 C12 117.96(13)
O2 S1 O3 120.07(7)
O2 S1 N1 107.86(6)
O3 S1 N1 104.44(6)
O2 S1 C9 110.05(7)
O3 S1 C9 107.98(7)
N1 S1 C9 105.39(6)
C2 Si1 C3 112.84(7)
C2 Si1 C1 108.74(7)
C3 Si1 C1 109.50(8)
C2 Si1 C4 108.11(6)
C3 Si1 C4 109.85(6)
C1 Si1 C4 107.66(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Si1 1.8686(16)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 Si1 1.8595(15)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 Si1 1.8617(15)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C8 1.3652(19)
C4 C5 1.4553(19)
C4 Si1 1.8867(14)
C5 O1 1.2198(16)
C5 N1 1.4293(17)
C6 C7 1.338(2)
C6 N1 1.3919(18)
C6 H6 0.9500
C7 C8 1.424(2)
C7 H7 0.9500
C8 H8 0.9500
C9 C14 1.387(2)
C9 C10 1.389(2)
C9 S1 1.7624(14)
C10 C11 1.384(2)
C10 H10 0.9500
C11 C12 1.380(2)
C11 H11 0.9500
C12 C13 1.383(2)
C12 N2 1.4793(19)
C13 C14 1.383(2)
C13 H13 0.9500
C14 H14 0.9500
N1 S1 1.7027(12)
N2 O5 1.2194(19)
N2 O4 1.2221(18)
O2 S1 1.4203(11)
O3 S1 1.4304(11)
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
C8 C4 C5 O1 174.27(13)
Si1 C4 C5 O1 -6.33(18)
C8 C4 C5 N1 -7.57(18)
Si1 C4 C5 N1 171.84(9)
N1 C6 C7 C8 -0.7(2)
C5 C4 C8 C7 -0.5(2)
Si1 C4 C8 C7 -179.87(12)
C6 C7 C8 C4 5.0(2)
C14 C9 C10 C11 -0.1(2)
S1 C9 C10 C11 -177.17(11)
C9 C10 C11 C12 0.7(2)
C10 C11 C12 C13 -0.6(2)
C10 C11 C12 N2 179.54(13)
C11 C12 C13 C14 0.0(2)
N2 C12 C13 C14 179.86(13)
C12 C13 C14 C9 0.5(2)
C10 C9 C14 C13 -0.5(2)
S1 C9 C14 C13 176.50(11)
C7 C6 N1 C5 -8.2(2)
C7 C6 N1 S1 167.76(12)
O1 C5 N1 C6 -169.62(13)
C4 C5 N1 C6 12.07(18)
O1 C5 N1 S1 14.43(16)
C4 C5 N1 S1 -163.88(9)
C11 C12 N2 O5 -8.0(2)
C13 C12 N2 O5 172.20(14)
C11 C12 N2 O4 171.73(14)
C13 C12 N2 O4 -8.1(2)
C6 N1 S1 O2 -130.05(11)
C5 N1 S1 O2 46.05(11)
C6 N1 S1 O3 -1.25(12)
C5 N1 S1 O3 174.85(10)
C6 N1 S1 C9 112.42(11)
C5 N1 S1 C9 -71.48(11)
C14 C9 S1 O2 -12.37(13)
C10 C9 S1 O2 164.77(11)
C14 C9 S1 O3 -145.15(12)
C10 C9 S1 O3 31.99(13)
C14 C9 S1 N1 103.67(12)
C10 C9 S1 N1 -79.19(12)
C8 C4 Si1 C2 130.89(12)
C5 C4 Si1 C2 -48.48(12)
C8 C4 Si1 C3 -105.59(13)
C5 C4 Si1 C3 75.03(11)
C8 C4 Si1 C1 13.58(14)
C5 C4 Si1 C1 -165.80(10)
