#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:09:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180290 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/04/7150438.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_7150438
loop_
_publ_author_name
'Ahmed, Omar'
'Hitchcock, Peter B.'
'Young, Douglas W.'
_publ_section_title
;
 Investigation of a route to ibotenic acid analogues via a reduced
 pyroglutamate template.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1596
_journal_page_last               1603
_journal_paper_doi               10.1039/b600195e
_journal_volume                  4
_journal_year                    2006
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C28 H39 N O6 Si'
_chemical_formula_structural     'C28 H39 N O6 Si'
_chemical_formula_sum            'C28 H39 N O6 Si'
_chemical_formula_weight         513.69
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2000-10-27T14:56:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 102.434(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6412(4)
_cell_length_b                   11.8424(9)
_cell_length_c                   15.8245(7)
_cell_measurement_reflns_used    4220
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     1398.37(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6757
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.78
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.22
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.22
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.3855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                3372
_reflns_number_total             3805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b600195e.txt
_cod_data_source_block           oct3700
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150438
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si 0.53002(9) 0.28615(7) 0.83925(5) 0.02261(19) Uani 1 1 d . . .
O1 O 0.4756(3) 0.6993(2) 0.76420(13) 0.0366(6) Uani 1 1 d . . .
O2 O 0.3845(3) 0.6296(2) 0.59228(13) 0.0386(6) Uani 1 1 d . . .
O3 O 0.5955(2) 0.5128(2) 0.55933(11) 0.0292(5) Uani 1 1 d . . .
O4 O 0.6493(2) 0.38900(18) 0.80946(11) 0.0236(5) Uani 1 1 d . B .
O6 O 0.9435(3) 0.7240(2) 0.70912(17) 0.0518(7) Uani 1 1 d . . .
N N 0.6295(3) 0.5731(2) 0.69482(14) 0.0226(5) Uani 1 1 d . . .
C1 C 0.6065(4) 0.6418(3) 0.76269(17) 0.0247(7) Uani 1 1 d . . .
C2 C 0.7920(3) 0.5023(3) 0.71869(17) 0.0230(6) Uani 1 1 d . B .
H2 H 0.8552 0.5 0.6695 0.028 Uiso 1 1 calc R . .
C3 C 0.9074(3) 0.5662(3) 0.79532(17) 0.0247(7) Uani 1 1 d . . .
H3 H 0.9724 0.5113 0.839 0.03 Uiso 1 1 calc R A 1
C4 C 0.7713(4) 0.6321(3) 0.83349(18) 0.0273(7) Uani 1 1 d . B .
H4A H 0.744 0.5916 0.8838 0.033 Uiso 1 1 calc R . .
H4B H 0.8184 0.708 0.8525 0.033 Uiso 1 1 calc R . .
C5 C 0.5211(4) 0.5770(3) 0.61197(18) 0.0269(7) Uani 1 1 d . . .
C6 C 0.5217(4) 0.5131(3) 0.46449(17) 0.0311(7) Uani 1 1 d . . .
C7 C 0.6567(5) 0.4387(4) 0.4328(2) 0.0447(10) Uani 1 1 d . . .
H7A H 0.6526 0.3622 0.4559 0.067 Uiso 1 1 calc R . .
H7B H 0.7773 0.47 0.4525 0.067 Uiso 1 1 calc R . .
H7C H 0.6271 0.436 0.3694 0.067 Uiso 1 1 calc R . .
C8 C 0.5224(5) 0.6317(3) 0.4306(2) 0.0430(9) Uani 1 1 d . . .
H8A H 0.6445 0.6621 0.4454 0.065 Uiso 1 1 calc R . .
H8B H 0.443 0.679 0.4567 0.065 Uiso 1 1 calc R . .
H8C H 0.4802 0.6313 0.3676 0.065 Uiso 1 1 calc R . .
C9 C 0.3370(4) 0.4592(4) 0.4449(2) 0.0448(9) Uani 1 1 d . . .
H9A H 0.3451 0.3823 0.4684 0.067 Uiso 1 1 calc R . .
H9B H 0.2913 0.4565 0.3821 0.067 Uiso 1 1 calc R . .
H9C H 0.2555 0.504 0.4715 0.067 Uiso 1 1 calc R . .
C10 C 0.7438(4) 0.3834(3) 0.74065(17) 0.0247(7) Uani 1 1 d . . .
H10A H 0.6676 0.3474 0.6892 0.03 Uiso 1 1 calc R B .
H10B H 0.8539 0.3377 0.7588 0.03 Uiso 1 1 calc R . .
C11 C 0.4757(4) 0.3394(3) 0.94263(17) 0.0278(7) Uani 1 1 d . . .
C12 C 0.6464(5) 0.3671(4) 1.0106(2) 0.0519(11) Uani 1 1 d . . .
H12A H 0.7181 0.4223 0.9866 0.078 Uiso 1 1 calc R . .
H12B H 0.7165 0.298 1.0262 0.078 Uiso 1 1 calc R . .
H12C H 0.6134 0.3987 1.0622 0.078 Uiso 1 1 calc R . .
C13 C 0.3660(5) 0.4480(3) 0.9233(2) 0.0439(9) Uani 1 1 d . . .
H13A H 0.4357 0.5047 0.8995 0.066 Uiso 1 1 calc R . .
H13B H 0.3375 0.4768 0.9768 0.066 Uiso 1 1 calc R . .
H13C H 0.2547 0.4322 0.881 0.066 Uiso 1 1 calc R . .
C14 C 0.3654(5) 0.2523(4) 0.9793(2) 0.0561(11) Uani 1 1 d . . .
H14A H 0.256 0.2352 0.9362 0.084 Uiso 1 1 calc R . .
H14B H 0.3334 0.2826 1.0316 0.084 Uiso 1 1 calc R . .
H14C H 0.436 0.1832 0.9938 0.084 Uiso 1 1 calc R . .
C15 C 0.6692(4) 0.1542(3) 0.85257(17) 0.0268(7) Uani 1 1 d . . .
C16 C 0.8439(4) 0.1568(3) 0.9035(2) 0.0358(8) Uani 1 1 d . . .
H16 H 0.8876 0.2246 0.9325 0.043 Uiso 1 1 calc R . .
C17 C 0.9538(4) 0.0629(3) 0.9123(2) 0.0400(8) Uani 1 1 d . . .
H17 H 1.071 0.0669 0.9477 0.048 Uiso 1 1 calc R . .
C18 C 0.8952(4) -0.0368(3) 0.8701(2) 0.0387(8) Uani 1 1 d . . .
H18 H 0.9718 -0.1009 0.8759 0.046 Uiso 1 1 calc R . .
C19 C 0.7243(4) -0.0420(3) 0.8196(2) 0.0378(8) Uani 1 1 d . . .
H19 H 0.682 -0.11 0.7904 0.045 Uiso 1 1 calc R . .
C20 C 0.6142(4) 0.0521(3) 0.81151(19) 0.0315(8) Uani 1 1 d . . .
H20 H 0.4966 0.0469 0.7766 0.038 Uiso 1 1 calc R . .
C21 C 0.3198(3) 0.2655(3) 0.75379(17) 0.0263(7) Uani 1 1 d . . .
C22 C 0.2045(4) 0.1732(3) 0.7533(2) 0.0335(8) Uani 1 1 d . . .
H22 H 0.2314 0.1189 0.7985 0.04 Uiso 1 1 calc R . .
C23 C 0.0510(4) 0.1595(3) 0.6880(2) 0.0402(9) Uani 1 1 d . . .
H23 H -0.0251 0.0963 0.6891 0.048 Uiso 1 1 calc R . .
C24 C 0.0098(4) 0.2371(4) 0.6220(2) 0.0401(9) Uani 1 1 d . . .
H24 H -0.0924 0.2264 0.5765 0.048 Uiso 1 1 calc R . .
C25 C 0.1183(4) 0.3308(3) 0.62244(19) 0.0378(9) Uani 1 1 d . . .
H25 H 0.0887 0.3858 0.578 0.045 Uiso 1 1 calc R . .
C26 C 0.2706(4) 0.3445(3) 0.68797(18) 0.0308(8) Uani 1 1 d . . .
H26 H 0.3431 0.4096 0.6877 0.037 Uiso 1 1 calc R . .
C28 C 1.0565(5) 0.7974(5) 0.6719(4) 0.098(2) Uani 1 1 d . B .
H28A H 0.9823 0.8529 0.6343 0.148 Uiso 1 1 calc R . .
H28B H 1.1242 0.7527 0.6378 0.148 Uiso 1 1 calc R . .
H28C H 1.1401 0.8368 0.7182 0.148 Uiso 1 1 calc R . .
C27 C 1.0414(4) 0.6431(3) 0.76494(19) 0.0304(7) Uani 0.597(6) 1 d P B 1
H27 H 1.1167 0.5976 0.7331 0.036 Uiso 0.597(6) 1 calc PR B 1
O5 O 1.1473(4) 0.6960(4) 0.8324(2) 0.0350(13) Uani 0.597(6) 1 d P B 1
H5 H 1.248 0.7084 0.821 0.053 Uiso 0.597(6) 1 calc PR B 1
C27A C 1.0414(4) 0.6431(3) 0.76494(19) 0.0304(7) Uani 0.403(6) 1 d P B 2
H27A H 1.1167 0.6821 0.8161 0.036 Uiso 0.403(6) 1 calc PR B 2
O5A O 1.1448(7) 0.5855(5) 0.7251(4) 0.0403(19) Uani 0.403(6) 1 d P B 2
H5A H 1.1477 0.617 0.6778 0.061 Uiso 0.403(6) 1 calc PR B 2
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 0 '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 0.006 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Si C15 108.20(11) . . ?
O4 Si C21 109.24(12) . . ?
C15 Si C21 110.38(14) . . ?
O4 Si C11 103.89(12) . . ?
C15 Si C11 114.04(13) . . ?
C21 Si C11 110.79(12) . . ?
C5 O3 C6 120.5(2) . . ?
C10 O4 Si 125.70(18) . . ?
C27 O6 C28 112.6(2) . . ?
C1 N C5 124.0(2) . . ?
C1 N C2 112.0(2) . . ?
C5 N C2 123.8(2) . . ?
O1 C1 N 125.9(3) . . ?
O1 C1 C4 126.2(3) . . ?
N C1 C4 107.9(2) . . ?
N C2 C10 110.7(2) . . ?
N C2 C3 103.3(2) . . ?
C10 C2 C3 113.8(2) . . ?
C27 C3 C4 112.4(3) . . ?
C27 C3 C2 110.9(2) . . ?
C4 C3 C2 103.9(2) . . ?
C1 C4 C3 106.1(2) . . ?
O2 C5 O3 126.5(3) . . ?
O2 C5 N 124.8(3) . . ?
O3 C5 N 108.7(2) . . ?
O3 C6 C8 109.5(3) . . ?
O3 C6 C9 109.8(2) . . ?
C8 C6 C9 113.2(3) . . ?
O3 C6 C7 101.3(2) . . ?
C8 C6 C7 111.6(3) . . ?
C9 C6 C7 110.8(3) . . ?
O4 C10 C2 108.6(2) . . ?
C14 C11 C13 108.8(3) . . ?
C14 C11 C12 109.5(3) . . ?
C13 C11 C12 107.8(3) . . ?
C14 C11 Si 110.4(2) . . ?
C13 C11 Si 108.7(2) . . ?
C12 C11 Si 111.5(2) . . ?
C20 C15 C16 116.2(3) . . ?
C20 C15 Si 124.3(2) . . ?
C16 C15 Si 119.5(3) . . ?
C17 C16 C15 121.5(3) . . ?
C16 C17 C18 120.8(3) . . ?
C19 C18 C17 119.1(3) . . ?
C18 C19 C20 119.9(3) . . ?
C19 C20 C15 122.5(3) . . ?
C26 C21 C22 116.9(3) . . ?
C26 C21 Si 120.2(2) . . ?
C22 C21 Si 122.9(2) . . ?
C23 C22 C21 121.4(3) . . ?
C24 C23 C22 120.2(3) . . ?
C23 C24 C25 119.5(3) . . ?
C24 C25 C26 120.1(3) . . ?
C21 C26 C25 121.9(3) . . ?
O5 C27 O6 109.1(3) . . ?
O5 C27 C3 111.0(3) . . ?
O6 C27 C3 107.7(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si O4 1.650(2) . ?
Si C15 1.877(3) . ?
Si C21 1.880(3) . ?
Si C11 1.881(3) . ?
O1 C1 1.214(3) . ?
O2 C5 1.198(3) . ?
O3 C5 1.341(4) . ?
O3 C6 1.485(3) . ?
O4 C10 1.432(3) . ?
O6 C27 1.405(4) . ?
O6 C28 1.438(4) . ?
N C1 1.389(4) . ?
N C5 1.393(3) . ?
N C2 1.478(3) . ?
C1 C4 1.499(4) . ?
C2 C10 1.514(4) . ?
C2 C3 1.537(4) . ?
C3 C27 1.523(4) . ?
C3 C4 1.525(4) . ?
C6 C8 1.503(5) . ?
C6 C9 1.519(4) . ?
C6 C7 1.522(5) . ?
C11 C14 1.523(5) . ?
C11 C13 1.530(5) . ?
C11 C12 1.536(4) . ?
C15 C20 1.393(5) . ?
C15 C16 1.403(4) . ?
C16 C17 1.382(5) . ?
C17 C18 1.382(5) . ?
C18 C19 1.378(5) . ?
C19 C20 1.386(5) . ?
C21 C26 1.390(4) . ?
C21 C22 1.403(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.376(5) . ?
C24 C25 1.385(5) . ?
C25 C26 1.392(4) . ?
C27 O5 1.347(4) . ?
