#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224832.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224832
loop_
_publ_author_name
'Guzei, Ilia A.'
'Spencer, Lara C.'
'Zakai, Uzma I.'
_publ_section_title
;
 2-{[(4-Methoxyphenyl)dimethylsilyl]methyl}isoindoline-1,3-dione
;
_journal_coeditor_code           ZS2023
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o219
_journal_page_last               o220
_journal_paper_doi               10.1107/S1600536809054129
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H19 N O3 Si'
_chemical_formula_moiety         'C18 H19 N O3 Si'
_chemical_formula_sum            'C18 H19 N O3 Si'
_chemical_formula_weight         325.43
_chemical_name_systematic
;
2-{[(4-Methoxyphenyl)dimethylsilyl]methyl}isoindoline-1,3-dione
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.355(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2713(16)
_cell_length_b                   14.061(3)
_cell_length_c                   12.069(2)
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.8277
_cell_measurement_theta_min      2.2596
_cell_volume                     1695.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'GIS (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), modiCIFer (Guzei, 2007)
and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009)
and FCF_filter (Guzei, 2007)
;
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11394
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.71
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_correction_T_min  0.9277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0457
_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)+(0.0812P)²+0.1363P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2338
_reflns_number_total             3197
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2023.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2224832
_cod_database_fobs_code          2224832
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si1 -0.00370(6) 0.19378(4) 0.82075(5) 0.0462(2) Uani d . 1 . .
O O1 -0.34928(17) 0.48107(11) 0.99174(16) 0.0762(5) Uani d . 1 . .
O O2 0.14405(16) -0.05076(11) 0.93970(14) 0.0674(5) Uani d . 1 . .
O O3 0.38001(16) 0.20812(11) 0.87061(17) 0.0779(5) Uani d . 1 . .
N N1 0.23597(15) 0.09334(11) 0.90879(13) 0.0439(4) Uani d . 1 . .
C C1 -0.3261(3) 0.57979(18) 0.9894(3) 0.0880(9) Uani d . 1 . .
H H1A -0.2364 0.5935 1.0307 0.132 Uiso calc R 1 . .
H H1B -0.3884 0.6127 1.0240 0.132 Uiso calc R 1 . .
H H1C -0.3377 0.6004 0.9119 0.132 Uiso calc R 1 . .
C C2 -0.2647(2) 0.42125(15) 0.95212(18) 0.0518(5) Uani d . 1 . .
C C3 -0.2964(2) 0.32606(16) 0.9526(2) 0.0603(6) Uani d . 1 . .
H H3 -0.3712 0.3068 0.9779 0.072 Uiso calc R 1 . .
C C4 -0.2182(2) 0.25971(15) 0.91604(18) 0.0532(5) Uani d . 1 . .
H H4 -0.2403 0.1958 0.9189 0.064 Uiso calc R 1 . .
C C5 -0.10617(18) 0.28429(13) 0.87447(16) 0.0426(5) Uani d . 1 . .
C C6 -0.0790(2) 0.38081(15) 0.87433(18) 0.0521(5) Uani d . 1 . .
H H6 -0.0060 0.4007 0.8470 0.063 Uiso calc R 1 . .
C C7 -0.1555(2) 0.44937(15) 0.91292(19) 0.0552(6) Uani d . 1 . .
H H7 -0.1330 0.5134 0.9122 0.066 Uiso calc R 1 . .
C C8 -0.1060(2) 0.08665(17) 0.7693(2) 0.0682(7) Uani d . 1 . .
H H8A -0.1350 0.0579 0.8316 0.102 Uiso calc R 1 . .
H H8B -0.0531 0.0419 0.7385 0.102 Uiso calc R 1 . .
H H8C -0.1827 0.1048 0.7112 0.102 Uiso calc R 1 . .
C C9 0.0661(3) 0.2458(2) 0.7055(2) 0.0755(7) Uani d . 1 . .
H H9A -0.0049 0.2730 0.6484 0.113 Uiso calc R 1 . .
H H9B 0.1098 0.1969 0.6719 0.113 Uiso calc R 1 . .
H H9C 0.1297 0.2944 0.7367 0.113 Uiso calc R 1 . .
C C10 0.1385(2) 0.15592(15) 0.94299(17) 0.0494(5) Uani d . 1 . .
H H10A 0.1844 0.2123 0.9785 0.059 Uiso calc R 1 . .
H H10B 0.1014 0.1235 0.9996 0.059 Uiso calc R 1 . .
C C11 0.2303(2) -0.00539(14) 0.91102(16) 0.0449(5) Uani d . 1 . .
C C12 0.34907(19) -0.03966(14) 0.87220(16) 0.0466(5) Uani d . 1 . .
C C13 0.3901(2) -0.13083(17) 0.85585(19) 0.0637(6) Uani d . 1 . .
H H13 0.3418 -0.1836 0.8699 0.076 Uiso calc R 1 . .
C C14 0.5067(3) -0.1404(2) 0.8175(2) 0.0792(8) Uani d . 1 . .
H H14 0.5375 -0.2009 0.8055 0.095 Uiso calc R 1 . .
C C15 0.5775(3) -0.0621(2) 0.7968(2) 0.0838(9) Uani d . 1 . .
H H15 0.6555 -0.0710 0.7715 0.101 Uiso calc R 1 . .
C C16 0.5365(2) 0.0289(2) 0.8124(2) 0.0713(7) Uani d . 1 . .
H H16 0.5847 0.0815 0.7977 0.086 Uiso calc R 1 . .
C C17 0.4204(2) 0.03886(15) 0.85097(17) 0.0498(5) Uani d . 1 . .
C C18 0.34950(19) 0.12526(16) 0.87585(17) 0.0515(5) Uani d . 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 Si1 C8 . . 110.81(13) ?
C9 Si1 C5 . . 109.82(10) ?
C8 Si1 C5 . . 110.42(10) ?
C9 Si1 C10 . . 109.38(11) ?
C8 Si1 C10 . . 107.86(10) ?
C5 Si1 C10 . . 108.48(8) ?
C2 O1 C1 . . 118.2(2) ?
C11 N1 C18 . . 111.69(16) ?
C11 N1 C10 . . 124.13(16) ?
C18 N1 C10 . . 124.10(17) ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C7 . . 125.3(2) ?
O1 C2 C3 . . 115.12(19) ?
C7 C2 C3 . . 119.63(19) ?
C4 C3 C2 . . 120.2(2) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 122.63(19) ?
C3 C4 H4 . . 118.7 ?
C5 C4 H4 . . 118.7 ?
C6 C5 C4 . . 115.11(18) ?
C6 C5 Si1 . . 122.64(15) ?
C4 C5 Si1 . . 122.24(15) ?
C5 C6 C7 . . 123.3(2) ?
C5 C6 H6 . . 118.3 ?
C7 C6 H6 . . 118.3 ?
C2 C7 C6 . . 119.06(19) ?
C2 C7 H7 . . 120.5 ?
C6 C7 H7 . . 120.5 ?
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 ?
N1 C10 Si1 . . 113.82(13) ?
N1 C10 H10A . . 108.8 ?
Si1 C10 H10A . . 108.8 ?
N1 C10 H10B . . 108.8 ?
Si1 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
O2 C11 N1 . . 124.82(18) ?
O2 C11 C12 . . 129.12(19) ?
N1 C11 C12 . . 106.06(17) ?
C13 C12 C17 . . 121.6(2) ?
C13 C12 C11 . . 130.4(2) ?
C17 C12 C11 . . 108.00(17) ?
C12 C13 C14 . . 117.0(2) ?
C12 C13 H13 . . 121.5 ?
C14 C13 H13 . . 121.5 ?
C15 C14 C13 . . 121.1(2) ?
C15 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
C16 C15 C14 . . 122.0(2) ?
C16 C15 H15 . . 119.0 ?
C14 C15 H15 . . 119.0 ?
C15 C16 C17 . . 117.1(3) ?
C15 C16 H16 . . 121.4 ?
C17 C16 H16 . . 121.4 ?
C12 C17 C16 . . 121.1(2) ?
C12 C17 C18 . . 108.11(18) ?
C16 C17 C18 . . 130.8(2) ?
O3 C18 N1 . . 124.7(2) ?
O3 C18 C17 . . 129.2(2) ?
N1 C18 C17 . . 106.09(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 C9 . 1.856(2) ?
Si1 C8 . 1.859(2) ?
Si1 C5 . 1.8609(19) ?
Si1 C10 . 1.897(2) ?
O1 C2 . 1.372(2) ?
O1 C1 . 1.410(3) ?
O2 C11 . 1.205(2) ?
O3 C18 . 1.212(2) ?
N1 C11 . 1.390(3) ?
N1 C18 . 1.390(2) ?
N1 C10 . 1.462(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.372(3) ?
C2 C3 . 1.378(3) ?
C3 C4 . 1.369(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.400(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(3) ?
C6 C7 . 1.390(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.485(3) ?
C12 C13 . 1.378(3) ?
C12 C17 . 1.381(3) ?
C13 C14 . 1.386(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.374(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.383(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.482(3) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 O1 C2 C7 . . . . 2.1(3) ?
C1 O1 C2 C3 . . . . -177.5(2) ?
O1 C2 C3 C4 . . . . -179.3(2) ?
C7 C2 C3 C4 . . . . 1.1(3) ?
C2 C3 C4 C5 . . . . -1.6(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C3 C4 C5 Si1 . . . . -178.04(17) ?
C9 Si1 C5 C6 . . . . -30.5(2) ?
C8 Si1 C5 C6 . . . . -153.00(17) ?
C10 Si1 C5 C6 . . . . 88.99(18) ?
C9 Si1 C5 C4 . . . . 148.23(18) ?
C8 Si1 C5 C4 . . . . 25.73(19) ?
C10 Si1 C5 C4 . . . . -92.27(18) ?
C4 C5 C6 C7 . . . . 0.4(3) ?
Si1 C5 C6 C7 . . . . 179.23(16) ?
O1 C2 C7 C6 . . . . -179.48(19) ?
C3 C2 C7 C6 . . . . 0.0(3) ?
C5 C6 C7 C2 . . . . -0.8(3) ?
C11 N1 C10 Si1 . . . . -93.1(2) ?
C18 N1 C10 Si1 . . . . 90.5(2) ?
C9 Si1 C10 N1 . . . . -53.22(18) ?
C8 Si1 C10 N1 . . . . 67.39(17) ?
C5 Si1 C10 N1 . . . . -172.99(14) ?
C18 N1 C11 O2 . . . . 177.87(19) ?
C10 N1 C11 O2 . . . . 1.1(3) ?
C18 N1 C11 C12 . . . . -2.0(2) ?
C10 N1 C11 C12 . . . . -178.81(15) ?
O2 C11 C12 C13 . . . . 1.9(4) ?
N1 C11 C12 C13 . . . . -178.2(2) ?
O2 C11 C12 C17 . . . . -178.8(2) ?
N1 C11 C12 C17 . . . . 1.1(2) ?
C17 C12 C13 C14 . . . . 0.2(3) ?
C11 C12 C13 C14 . . . . 179.45(19) ?
C12 C13 C14 C15 . . . . 0.0(4) ?
C13 C14 C15 C16 . . . . -0.3(4) ?
C14 C15 C16 C17 . . . . 0.4(4) ?
C13 C12 C17 C16 . . . . -0.1(3) ?
C11 C12 C17 C16 . . . . -179.46(18) ?
C13 C12 C17 C18 . . . . 179.50(18) ?
C11 C12 C17 C18 . . . . 0.1(2) ?
C15 C16 C17 C12 . . . . -0.3(3) ?
C15 C16 C17 C18 . . . . -179.7(2) ?
C11 N1 C18 O3 . . . . -177.6(2) ?
C10 N1 C18 O3 . . . . -0.8(3) ?
C11 N1 C18 C17 . . . . 2.1(2) ?
C10 N1 C18 C17 . . . . 178.88(16) ?
C12 C17 C18 O3 . . . . 178.3(2) ?
C16 C17 C18 O3 . . . . -2.2(4) ?
C12 C17 C18 N1 . . . . -1.3(2) ?
C16 C17 C18 N1 . . . . 178.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744149
