#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/87/4068706.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_4068706
loop_
_publ_author_name
'Lippe, Katrin'
'Gerlach, Daniela'
'Kroke, Edwin'
'Wagler, Jörg'
_publ_section_title
;
 Hypercoordinate Organosilicon Complexes of an ONN′O′
 Chelating Ligand: Regio- and Diastereoselectivity of Rearrangement
 Reactions in Si−Salphen Systems
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              621
_journal_paper_doi               10.1021/om801049q
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C34 H28 N2 O4'
_chemical_formula_sum            'C34 H28 N2 O4'
_chemical_formula_weight         528.58
_chemical_melting_point          512
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_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                 112.577(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.5225(10)
_cell_length_b                   8.4242(7)
_cell_length_c                   13.9239(10)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      37.82
_cell_measurement_theta_min      2.99
_cell_volume                     1356.29(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP32 (Farugia)'
_computing_publication_material  'Ciftab (Sheldrick)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16715
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       piece
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0400
_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)+(0.0501P)²+0.4612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2945
_reflns_number_total             3275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om801049q_si_001.cif
_cod_data_source_block           compound_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '512 K' was changed to '512' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1356.29(18)
_cod_original_sg_symbol_Hall     -P2yc
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4068706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
O1 O 0.02886(6) 0.33399(9) 0.04103(6) 0.01939(17) Uani 1 1 d .
H1 H 0.0229(12) 0.4140(19) 0.0814(11) 0.029 Uiso 1 1 d .
O2 O 0.29556(6) -0.08893(9) 0.08030(6) 0.02086(17) Uani 1 1 d .
N1 N 0.07413(7) 0.52527(9) 0.19707(6) 0.01427(17) Uani 1 1 d .
C1 C 0.13101(8) 0.26493(11) 0.09651(7) 0.01393(19) Uani 1 1 d .
C2 C 0.15926(8) 0.12685(11) 0.05561(7) 0.01547(19) Uani 1 1 d .
H2 H 0.1094 0.0882 -0.0106 0.019 Uiso 1 1 calc R
C3 C 0.26057(8) 0.04696(11) 0.11250(8) 0.0158(2) Uani 1 1 d .
C4 C 0.33522(8) 0.10358(12) 0.20963(8) 0.0179(2) Uani 1 1 d .
H4 H 0.4030 0.0460 0.2495 0.022 Uiso 1 1 calc R
C5 C 0.30918(8) 0.24371(12) 0.24673(7) 0.0163(2) Uani 1 1 d .
H5 H 0.3617 0.2842 0.3113 0.020 Uiso 1 1 calc R
C6 C 0.20731(8) 0.32858(11) 0.19198(7) 0.01362(19) Uani 1 1 d .
C7 C 0.17951(8) 0.47509(11) 0.23468(7) 0.01334(19) Uani 1 1 d .
C8 C 0.27517(8) 0.56029(11) 0.31845(7) 0.01473(19) Uani 1 1 d .
C9 C 0.36627(9) 0.62307(13) 0.29647(8) 0.0196(2) Uani 1 1 d .
H9 H 0.3697 0.6054 0.2303 0.024 Uiso 1 1 calc R
C10 C 0.45197(9) 0.71134(13) 0.37104(9) 0.0236(2) Uani 1 1 d .
H10 H 0.5125 0.7575 0.3552 0.028 Uiso 1 1 calc R
C11 C 0.44875(9) 0.73183(13) 0.46903(9) 0.0246(2) Uani 1 1 d .
H11 H 0.5075 0.7919 0.5202 0.030 Uiso 1 1 calc R
C12 C 0.36046(10) 0.66520(13) 0.49242(8) 0.0232(2) Uani 1 1 d .
H12 H 0.3602 0.6766 0.5602 0.028 Uiso 1 1 calc R
C13 C 0.27228(9) 0.58168(12) 0.41681(8) 0.0185(2) Uani 1 1 d .
H13 H 0.2102 0.5393 0.4320 0.022 Uiso 1 1 calc R
C14 C 0.22933(10) -0.14170(14) -0.02333(9) 0.0259(2) Uani 1 1 d .
H14A H 0.1507 -0.1679 -0.0296 0.039 Uiso 1 1 calc R
H14B H 0.2658 -0.2361 -0.0386 0.039 Uiso 1 1 calc R
H14C H 0.2262 -0.0572 -0.0727 0.039 Uiso 1 1 calc R
C15 C 0.04177(8) 0.67238(11) 0.22790(7) 0.01350(19) Uani 1 1 d .
C16 C 0.08292(9) 0.81601(12) 0.20625(7) 0.0165(2) Uani 1 1 d .
H16 H 0.1394 0.8163 0.1762 0.020 Uiso 1 1 calc R
C17 C 0.04174(9) 0.95863(12) 0.22832(7) 0.0178(2) Uani 1 1 d .
H17 H 0.0705 1.0563 0.2139 0.021 Uiso 1 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'
N N 0.0061 0.0033 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 H1 104.7(9) . .
C3 O2 C14 117.25(8) . .
C7 N1 C15 121.96(8) . .
O1 C1 C2 117.31(8) . .
O1 C1 C6 121.79(8) . .
C2 C1 C6 120.91(9) . .
C3 C2 C1 119.38(9) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
O2 C3 C2 124.06(9) . .
O2 C3 C4 115.13(8) . .
C2 C3 C4 120.81(9) . .
C5 C4 C3 119.21(9) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 121.96(9) . .
C4 C5 H5 119.0 . .
C6 C5 H5 119.0 . .
C5 C6 C1 117.59(8) . .
C5 C6 C7 121.00(8) . .
C1 C6 C7 121.37(8) . .
N1 C7 C6 118.40(8) . .
N1 C7 C8 123.20(8) . .
C6 C7 C8 118.40(8) . .
C9 C8 C13 119.88(9) . .
C9 C8 C7 119.26(8) . .
C13 C8 C7 120.83(9) . .
C10 C9 C8 120.13(9) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 119.66(10) . .
C9 C10 H10 120.2 . .
C11 C10 H10 120.2 . .
C12 C11 C10 120.43(10) . .
C12 C11 H11 119.8 . .
C10 C11 H11 119.8 . .
C11 C12 C13 120.06(10) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C12 C13 C8 119.77(10) . .
C12 C13 H13 120.1 . .
C8 C13 H13 120.1 . .
O2 C14 H14A 109.5 . .
O2 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
O2 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C16 C15 C15 119.68(5) . 2
C16 C15 N1 121.36(8) . .
C15 C15 N1 118.68(5) 2 .
C17 C16 C15 120.30(9) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C16 C17 C17 120.02(6) . 2
C16 C17 H17 120.0 . .
C17 C17 H17 120.0 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3463(11) .
O1 H1 0.899(16) .
O2 C3 1.3617(11) .
O2 C14 1.4313(13) .
N1 C7 1.2899(12) .
N1 C15 1.4205(12) .
C1 C2 1.3990(13) .
C1 C6 1.4115(13) .
C2 C3 1.3850(13) .
C2 H2 0.9500 .
C3 C4 1.3999(14) .
C4 C5 1.3769(14) .
C4 H4 0.9500 .
C5 C6 1.4047(13) .
C5 H5 0.9500 .
C6 C7 1.4686(13) .
C7 C8 1.4959(12) .
C8 C9 1.3938(14) .
C8 C13 1.3956(13) .
C9 C10 1.3882(14) .
C9 H9 0.9500 .
C10 C11 1.3911(16) .
C10 H10 0.9500 .
C11 C12 1.3856(17) .
C11 H11 0.9500 .
C12 C13 1.3892(15) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 C16 1.3927(13) .
C15 C15 1.4027(18) 2
C16 C17 1.3876(14) .
C16 H16 0.9500 .
C17 C17 1.394(2) 2
C17 H17 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 -176.61(8) . .
C6 C1 C2 C3 3.59(14) . .
C14 O2 C3 C2 6.96(14) . .
C14 O2 C3 C4 -173.02(9) . .
C1 C2 C3 O2 179.41(8) . .
C1 C2 C3 C4 -0.62(14) . .
O2 C3 C4 C5 177.49(8) . .
C2 C3 C4 C5 -2.49(15) . .
C3 C4 C5 C6 2.70(15) . .
C4 C5 C6 C1 0.19(14) . .
C4 C5 C6 C7 177.98(9) . .
O1 C1 C6 C5 176.85(8) . .
C2 C1 C6 C5 -3.36(13) . .
O1 C1 C6 C7 -0.94(14) . .
C2 C1 C6 C7 178.85(8) . .
C15 N1 C7 C6 -174.76(8) . .
C15 N1 C7 C8 4.20(14) . .
C5 C6 C7 N1 -161.88(9) . .
C1 C6 C7 N1 15.83(13) . .
C5 C6 C7 C8 19.11(13) . .
C1 C6 C7 C8 -163.17(8) . .
N1 C7 C8 C9 -115.56(11) . .
C6 C7 C8 C9 63.40(12) . .
N1 C7 C8 C13 62.44(13) . .
C6 C7 C8 C13 -118.60(10) . .
C13 C8 C9 C10 -2.19(15) . .
C7 C8 C9 C10 175.83(9) . .
C8 C9 C10 C11 2.37(16) . .
C9 C10 C11 C12 -0.22(17) . .
C10 C11 C12 C13 -2.12(16) . .
C11 C12 C13 C8 2.30(15) . .
C9 C8 C13 C12 -0.15(15) . .
C7 C8 C13 C12 -178.14(9) . .
C7 N1 C15 C16 64.78(13) . .
C7 N1 C15 C15 -121.33(12) . 2
C15 C15 C16 C17 0.08(16) 2 .
N1 C15 C16 C17 173.91(9) . .
C15 C16 C17 C17 -0.45(17) . 2
