#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154538.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_7154538
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            'C15 H16 N2 O7 S Si'
_chemical_formula_weight         396.45
_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                 101.968(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5825(3)
_cell_length_b                   10.5322(2)
_cell_length_c                   12.8580(3)
_cell_measurement_reflns_used    3477
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.63
_cell_measurement_theta_min      3.33
_cell_volume                     1799.40(7)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9327
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         67.80
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    2.617
_exptl_absorpt_correction_T_max  0.7798
_exptl_absorpt_correction_T_min  0.477511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0367
_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)+(0.0498P)²+0.5335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2774
_reflns_number_total             3225
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01239b2.cif
_cod_data_source_block           s3727na
_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_sg_symbol_H-M      P2(1)/c
_cod_database_code               7154538
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 0.26980(14) 0.63612(18) 0.95705(14) 0.0197(4) Uani 1 1 d .
C2 C 0.34209(13) 0.59998(18) 0.90092(14) 0.0197(4) Uani 1 1 d .
C3 C 0.34966(15) 0.46823(19) 0.88626(16) 0.0250(4) Uani 1 1 d .
H3 H 0.3973 0.4372 0.8478 0.030 Uiso 1 1 calc R
C4 C 0.28929(15) 0.3820(2) 0.92646(17) 0.0277(4) Uani 1 1 d .
H4 H 0.2951 0.2937 0.9139 0.033 Uiso 1 1 calc R
C5 C 0.22057(15) 0.4249(2) 0.98480(16) 0.0270(4) Uani 1 1 d .
H5 H 0.1806 0.3659 1.0136 0.032 Uiso 1 1 calc R
C6 C 0.21033(14) 0.5542(2) 1.00094(15) 0.0252(4) Uani 1 1 d .
H6 H 0.1639 0.5852 1.0409 0.030 Uiso 1 1 calc R
C7 C 0.52677(16) 0.6290(2) 0.80320(19) 0.0345(5) Uani 1 1 d .
H7A H 0.5753 0.6887 0.7837 0.052 Uiso 1 1 calc R
H7B H 0.4955 0.5791 0.7407 0.052 Uiso 1 1 calc R
H7C H 0.5616 0.5719 0.8591 0.052 Uiso 1 1 calc R
C8 C 0.35127(18) 0.8144(2) 0.74274(17) 0.0331(5) Uani 1 1 d .
H8A H 0.3961 0.8571 0.7031 0.050 Uiso 1 1 calc R
H8B H 0.3123 0.8780 0.7725 0.050 Uiso 1 1 calc R
H8C H 0.3053 0.7582 0.6948 0.050 Uiso 1 1 calc R
C9 C 0.48767(16) 0.8224(2) 0.96641(18) 0.0328(5) Uani 1 1 d .
H9A H 0.5113 0.7699 1.0296 0.049 Uiso 1 1 calc R
H9B H 0.4383 0.8840 0.9811 0.049 Uiso 1 1 calc R
H9C H 0.5448 0.8675 0.9481 0.049 Uiso 1 1 calc R
C10 C 0.11190(13) 0.87424(18) 1.04216(14) 0.0190(4) Uani 1 1 d .
C11 C 0.14525(13) 0.96516(18) 1.12046(14) 0.0190(4) Uani 1 1 d .
C12 C 0.09485(14) 0.98780(18) 1.20128(15) 0.0214(4) Uani 1 1 d .
H12 H 0.1173 1.0508 1.2537 0.026 Uiso 1 1 calc R
C13 C 0.01073(14) 0.91561(18) 1.20300(14) 0.0211(4) Uani 1 1 d .
C14 C -0.02595(14) 0.82579(19) 1.12706(16) 0.0238(4) Uani 1 1 d .
H14 H -0.0845 0.7780 1.1308 0.029 Uiso 1 1 calc R
C15 C 0.02456(14) 0.80651(19) 1.04472(16) 0.0240(4) Uani 1 1 d .
H15 H -0.0006 0.7470 0.9902 0.029 Uiso 1 1 calc R
N1 N 0.23707(12) 1.04033(16) 1.12213(13) 0.0244(4) Uani 1 1 d .
N2 N -0.04208(12) 0.93459(17) 1.29121(13) 0.0268(4) Uani 1 1 d .
O1 O 0.26480(10) 0.76982(13) 0.97750(10) 0.0224(3) Uani 1 1 d .
O2 O 0.10094(11) 0.77963(15) 0.85381(11) 0.0299(3) Uani 1 1 d .
O3 O 0.20447(11) 0.97160(14) 0.90463(11) 0.0290(3) Uani 1 1 d .
O4 O 0.31498(10) 0.98289(14) 1.12378(12) 0.0301(3) Uani 1 1 d .
O5 O 0.22881(13) 1.15525(14) 1.12535(16) 0.0440(4) Uani 1 1 d .
O6 O -0.10776(12) 0.85893(17) 1.29994(13) 0.0384(4) Uani 1 1 d .
O7 O -0.01575(12) 1.02433(16) 1.35104(12) 0.0370(4) Uani 1 1 d .
S1 S 0.16915(3) 0.85133(4) 0.93099(3) 0.02122(15) Uani 1 1 d .
Si1 Si 0.42785(4) 0.71894(5) 0.85293(4) 0.02233(15) 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'
S S 0.3331 0.5567 '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
C6 C1 C2 125.35(18)
C6 C1 O1 118.97(17)
C2 C1 O1 115.45(16)
C1 C2 C3 114.81(17)
C1 C2 Si1 122.43(14)
C3 C2 Si1 122.71(14)
C4 C3 C2 121.89(18)
C4 C3 H3 119.1
C2 C3 H3 119.1
C5 C4 C3 120.10(19)
C5 C4 H4 119.9
C3 C4 H4 119.9
C6 C5 C4 119.96(19)
C6 C5 H5 120.0
C4 C5 H5 120.0
C1 C6 C5 117.82(18)
C1 C6 H6 121.1
C5 C6 H6 121.1
Si1 C7 H7A 109.5
Si1 C7 H7B 109.5
H7A C7 H7B 109.5
Si1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
Si1 C8 H8A 109.5
Si1 C8 H8B 109.5
H8A C8 H8B 109.5
Si1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
Si1 C9 H9A 109.5
Si1 C9 H9B 109.5
H9A C9 H9B 109.5
Si1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C15 C10 C11 119.07(17)
C15 C10 S1 117.81(14)
C11 C10 S1 122.83(14)
C12 C11 C10 121.67(17)
C12 C11 N1 116.56(17)
C10 C11 N1 121.76(16)
C13 C12 C11 117.40(18)
C13 C12 H12 121.3
C11 C12 H12 121.3
C14 C13 C12 123.22(17)
C14 C13 N2 118.43(17)
C12 C13 N2 118.35(17)
C13 C14 C15 118.50(18)
C13 C14 H14 120.7
C15 C14 H14 120.7
C10 C15 C14 120.07(18)
C10 C15 H15 120.0
C14 C15 H15 120.0
O5 N1 O4 125.50(18)
O5 N1 C11 116.81(16)
O4 N1 C11 117.65(16)
O6 N2 O7 124.82(17)
O6 N2 C13 117.64(17)
O7 N2 C13 117.53(17)
C1 O1 S1 122.24(12)
O3 S1 O2 120.62(9)
O3 S1 O1 106.57(8)
O2 S1 O1 110.05(8)
O3 S1 C10 107.23(9)
O2 S1 C10 107.57(9)
O1 S1 C10 103.49(8)
C7 Si1 C9 109.71(10)
C7 Si1 C8 109.96(11)
C9 Si1 C8 111.24(11)
C7 Si1 C2 108.12(10)
C9 Si1 C2 109.15(9)
C8 Si1 C2 108.60(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.380(3)
C1 C2 1.387(3)
C1 O1 1.437(2)
C2 C3 1.407(3)
C2 Si1 1.8989(19)
C3 C4 1.393(3)
C3 H3 0.9500
C4 C5 1.389(3)
C4 H4 0.9500
C5 C6 1.388(3)
C5 H5 0.9500
C6 H6 0.9500
C7 Si1 1.862(2)
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 Si1 1.868(2)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 Si1 1.867(2)
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 C15 1.390(3)
C10 C11 1.395(3)
C10 S1 1.7796(18)
C11 C12 1.379(3)
C11 N1 1.474(2)
C12 C13 1.376(3)
C12 H12 0.9500
C13 C14 1.376(3)
C13 N2 1.476(2)
C14 C15 1.391(3)
C14 H14 0.9500
C15 H15 0.9500
N1 O5 1.217(2)
N1 O4 1.215(2)
N2 O6 1.219(2)
N2 O7 1.224(2)
O1 S1 1.5685(13)
O2 S1 1.4256(15)
O3 S1 1.4203(16)
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
C6 C1 C2 C3 2.6(3)
O1 C1 C2 C3 176.86(16)
C6 C1 C2 Si1 -174.91(15)
O1 C1 C2 Si1 -0.6(2)
C1 C2 C3 C4 -0.6(3)
Si1 C2 C3 C4 176.88(15)
C2 C3 C4 C5 -1.4(3)
C3 C4 C5 C6 1.5(3)
C2 C1 C6 C5 -2.5(3)
O1 C1 C6 C5 -176.55(16)
C4 C5 C6 C1 0.3(3)
C15 C10 C11 C12 1.2(3)
S1 C10 C11 C12 174.86(14)
C15 C10 C11 N1 -179.87(17)
S1 C10 C11 N1 -6.2(3)
C10 C11 C12 C13 1.0(3)
N1 C11 C12 C13 -177.95(16)
C11 C12 C13 C14 -1.8(3)
C11 C12 C13 N2 177.58(16)
C12 C13 C14 C15 0.3(3)
N2 C13 C14 C15 -179.09(17)
C11 C10 C15 C14 -2.8(3)
S1 C10 C15 C14 -176.73(15)
C13 C14 C15 C10 2.1(3)
C12 C11 N1 O5 -54.5(2)
C10 C11 N1 O5 126.5(2)
C12 C11 N1 O4 123.05(19)
C10 C11 N1 O4 -55.9(2)
C14 C13 N2 O6 9.1(3)
C12 C13 N2 O6 -170.27(18)
C14 C13 N2 O7 -171.78(18)
C12 C13 N2 O7 8.8(3)
C6 C1 O1 S1 -68.7(2)
C2 C1 O1 S1 116.63(16)
C1 O1 S1 O3 -142.98(14)
C1 O1 S1 O2 -10.59(16)
C1 O1 S1 C10 104.12(14)
C15 C10 S1 O3 141.06(15)
C11 C10 S1 O3 -32.66(18)
C15 C10 S1 O2 9.95(17)
C11 C10 S1 O2 -163.76(15)
C15 C10 S1 O1 -106.52(15)
C11 C10 S1 O1 79.76(16)
C1 C2 Si1 C7 170.23(16)
C3 C2 Si1 C7 -7.06(19)
C1 C2 Si1 C9 50.94(18)
C3 C2 Si1 C9 -126.35(17)
C1 C2 Si1 C8 -70.49(17)
C3 C2 Si1 C8 112.22(17)
