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#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/43/4074340.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_4074340
loop_
_publ_author_name
'Ilg, Rainer'
'Burschka, Christian'
'Schepmann, Dirk'
'Wünsch, Bernhard'
'Tacke, Reinhold'
_publ_section_title
;
 Synthesis and Pharmacological Characterization of Sila-panamesine, a
 Sila-Analogue of the σ Receptor Ligand Panamesine (EMD 57445)
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              5396
_journal_paper_doi               10.1021/om060562c
_journal_volume                  25
_journal_year                    2006
_chemical_formula_moiety         'C18 H20N O4 Si .  Cl '
_chemical_formula_sum            'C18 H20 Cl N O4 Si'
_chemical_formula_weight         377.89
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.3219(6)
_cell_length_b                   11.1170(7)
_cell_length_c                   30.546(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      6.65
_cell_volume                     3505.1(4)
_computing_cell_refinement       Stoe-IPDS
_computing_data_collection       Stoe-IPDS
_computing_data_reduction        Stoe-IPDS
_computing_molecular_graphics    Bruker-SHELXTL
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Stoe-IPDS
_diffrn_measurement_method       Stoe-IPDS
_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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20979
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelets
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .15
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0373
_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)+(0.0545P)²+1.4153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2695
_reflns_number_total             3567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om060562csi20060628_094023.cif
_cod_data_source_block           12_ilg12du
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4074340
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
Cl Cl 0.17458(5) 0.62410(4) 0.266904(16) 0.03557(14) Uani 1 1 d .
Si Si 0.92154(5) 0.29705(4) 0.356506(16) 0.02572(13) Uani 1 1 d .
O3 O 1.14248(15) -0.12821(12) 0.33168(4) 0.0381(4) Uani 1 1 d .
O4 O 1.15072(15) -0.18054(12) 0.40483(5) 0.0388(4) Uani 1 1 d .
N N 0.78363(17) 0.38513(15) 0.26972(5) 0.0301(4) Uani 1 1 d .
HN1A H 0.743(2) 0.441(2) 0.2532(7) 0.036 Uiso 1 1 d .
HN1B H 0.793(2) 0.311(2) 0.2564(7) 0.036 Uiso 1 1 d .
C1 C 0.93096(19) 0.41873(16) 0.39883(6) 0.0286(4) Uani 1 1 d .
O2 O 0.95483(18) 0.69292(16) 0.48996(5) 0.0531(4) Uani 1 1 d .
C8 C 0.99975(18) 0.15411(16) 0.37519(6) 0.0263(4) Uani 1 1 d .
C10 C 1.09142(18) -0.03605(16) 0.35686(6) 0.0275(4) Uani 1 1 d .
C2 C 0.8221(2) 0.4628(2) 0.42153(7) 0.0392(5) Uani 1 1 d .
H2 H 0.7380 0.4309 0.4165 0.047 Uiso 1 1 calc R
C18 C 0.7490(2) 0.26812(17) 0.33945(6) 0.0308(4) Uani 1 1 d .
H18A H 0.7439 0.1883 0.3252 0.037 Uiso 1 1 calc R
H18B H 0.6936 0.2657 0.3659 0.037 Uiso 1 1 calc R
C17 C 0.6961(2) 0.36352(18) 0.30796(6) 0.0338(4) Uani 1 1 d .
H17A H 0.6102 0.3374 0.2971 0.041 Uiso 1 1 calc R
H17B H 0.6841 0.4400 0.3241 0.041 Uiso 1 1 calc R
C13 C 1.0090(2) 0.12216(18) 0.41934(6) 0.0332(4) Uani 1 1 d .
H13 H 0.9812 0.1781 0.4409 0.040 Uiso 1 1 calc R
C9 C 1.04425(19) 0.07233(16) 0.34305(6) 0.0294(4) Uani 1 1 d .
H9 H 1.0414 0.0922 0.3128 0.035 Uiso 1 1 calc R
C15 C 1.00063(19) 0.35124(17) 0.30476(6) 0.0287(4) Uani 1 1 d .
H15A H 1.0835 0.3914 0.3120 0.034 Uiso 1 1 calc R
H15B H 1.0200 0.2816 0.2856 0.034 Uiso 1 1 calc R
C16 C 0.91290(19) 0.43913(17) 0.28040(7) 0.0315(4) Uani 1 1 d .
H16A H 0.8999 0.5118 0.2986 0.038 Uiso 1 1 calc R
H16B H 0.9559 0.4643 0.2529 0.038 Uiso 1 1 calc R
C4 C 0.9629(2) 0.60311(18) 0.45887(6) 0.0368(5) Uani 1 1 d .
C5 C 1.0712(2) 0.56127(19) 0.43821(7) 0.0392(5) Uani 1 1 d .
H5 H 1.1548 0.5931 0.4441 0.047 Uiso 1 1 calc R
C11 C 1.09701(19) -0.06720(17) 0.40062(6) 0.0308(4) Uani 1 1 d .
C12 C 1.0579(2) 0.01036(18) 0.43299(7) 0.0382(5) Uani 1 1 d .
H12 H 1.0635 -0.0105 0.4631 0.046 Uiso 1 1 calc R
C6 C 1.0522(2) 0.46876(18) 0.40779(7) 0.0364(5) Uani 1 1 d .
H6 H 1.1254 0.4385 0.3925 0.044 Uiso 1 1 calc R
C14 C 1.1503(2) -0.22898(17) 0.36097(7) 0.0359(5) Uani 1 1 d .
H14A H 1.2306 -0.2753 0.3555 0.043 Uiso 1 1 calc R
H14B H 1.0751 -0.2830 0.3568 0.043 Uiso 1 1 calc R
O1 O 0.75171(19) 0.6080(2) 0.47850(6) 0.0731(6) Uani 1 1 d .
C3 C 0.8420(2) 0.5539(2) 0.45127(7) 0.0425(5) Uani 1 1 d .
C7 C 0.8199(3) 0.7053(2) 0.49924(8) 0.0561(7) Uani 1 1 d .
H7A H 0.7878 0.7833 0.4880 0.067 Uiso 1 1 calc R
H7B H 0.8053 0.7031 0.5313 0.067 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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C8 Si C1 112.34(8)
C8 Si C15 109.97(8)
C1 Si C15 109.06(8)
C8 Si C18 110.32(8)
C1 Si C18 111.30(9)
C15 Si C18 103.47(9)
C10 O3 C14 104.63(14)
C11 O4 C14 104.62(14)
C17 N C16 115.59(15)
C6 C1 C2 118.68(18)
C6 C1 Si 117.99(14)
C2 C1 Si 123.33(15)
C4 O2 C7 105.36(18)
C13 C8 C9 118.95(17)
C13 C8 Si 122.65(14)
C9 C8 Si 118.30(14)
C9 C10 C11 122.31(17)
C9 C10 O3 128.05(17)
C11 C10 O3 109.62(16)
C3 C2 C1 117.5(2)
C17 C18 Si 113.10(13)
N C17 C18 112.70(16)
C8 C13 C12 122.40(18)
C10 C9 C8 117.92(17)
C16 C15 Si 110.97(13)
N C16 C15 112.21(15)
C5 C4 O2 127.8(2)
C5 C4 C3 121.78(18)
O2 C4 C3 110.36(19)
C4 C5 C6 116.2(2)
C12 C11 C10 121.80(18)
C12 C11 O4 128.56(18)
C10 C11 O4 109.58(16)
C11 C12 C13 116.58(18)
C1 C6 C5 123.3(2)
O3 C14 O4 106.70(14)
C3 O1 C7 105.2(2)
C2 C3 C4 122.5(2)
C2 C3 O1 128.0(2)
C4 C3 O1 109.50(19)
O2 C7 O1 108.52(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si C8 1.8715(19)
Si C1 1.8737(19)
Si C15 1.8783(19)
Si C18 1.883(2)
O3 C10 1.385(2)
O3 C14 1.436(2)
O4 C11 1.382(2)
O4 C14 1.444(2)
N C17 1.496(3)
N C16 1.499(3)
C1 C6 1.396(3)
C1 C2 1.409(3)
O2 C4 1.380(2)
O2 C7 1.428(3)
C8 C13 1.398(3)
C8 C9 1.415(3)
C10 C9 1.366(3)
C10 C11 1.382(3)
C2 C3 1.375(3)
C18 C17 1.532(3)
C13 C12 1.405(3)
C15 C16 1.526(3)
C4 C5 1.366(3)
C4 C3 1.382(3)
C5 C6 1.400(3)
C11 C12 1.373(3)
O1 C3 1.387(3)
O1 C7 1.437(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
C8 Si C1 C6 69.46(17)
C15 Si C1 C6 -52.72(17)
C18 Si C1 C6 -166.26(15)
C8 Si C1 C2 -111.31(17)
C15 Si C1 C2 126.51(17)
C18 Si C1 C2 12.97(19)
C1 Si C8 C13 27.49(19)
C15 Si C8 C13 149.17(16)
C18 Si C8 C13 -97.33(18)
C1 Si C8 C9 -156.30(15)
C15 Si C8 C9 -34.63(18)
C18 Si C8 C9 78.88(17)
C14 O3 C10 C9 -167.8(2)
C14 O3 C10 C11 13.8(2)
C6 C1 C2 C3 0.3(3)
Si C1 C2 C3 -178.90(16)
C8 Si C18 C17 -157.44(13)
C1 Si C18 C17 77.15(15)
C15 Si C18 C17 -39.85(15)
C16 N C17 C18 -65.6(2)
Si C18 C17 N 51.00(19)
C9 C8 C13 C12 -1.7(3)
Si C8 C13 C12 174.50(17)
C11 C10 C9 C8 -0.2(3)
O3 C10 C9 C8 -178.40(18)
C13 C8 C9 C10 1.7(3)
Si C8 C9 C10 -174.69(15)
C8 Si C15 C16 160.28(13)
C1 Si C15 C16 -76.11(15)
C18 Si C15 C16 42.44(15)
C17 N C16 C15 69.8(2)
Si C15 C16 N -57.28(18)
C7 O2 C4 C5 177.3(2)
C7 O2 C4 C3 -4.7(3)
O2 C4 C5 C6 -180.0(2)
C3 C4 C5 C6 2.2(3)
C9 C10 C11 C12 -1.4(3)
O3 C10 C11 C12 177.10(19)
C9 C10 C11 O4 -179.03(18)
O3 C10 C11 O4 -0.5(2)
C14 O4 C11 C12 169.7(2)
C14 O4 C11 C10 -12.9(2)
C10 C11 C12 C13 1.4(3)
O4 C11 C12 C13 178.5(2)
C8 C13 C12 C11 0.1(3)
C2 C1 C6 C5 -0.2(3)
Si C1 C6 C5 179.03(17)
C4 C5 C6 C1 -1.0(3)
C10 O3 C14 O4 -21.5(2)
C11 O4 C14 O3 21.2(2)
C1 C2 C3 C4 0.9(3)
C1 C2 C3 O1 -177.2(2)
C5 C4 C3 C2 -2.2(4)
O2 C4 C3 C2 179.6(2)
C5 C4 C3 O1 176.2(2)
O2 C4 C3 O1 -2.0(3)
C7 O1 C3 C2 -174.0(2)
C7 O1 C3 C4 7.7(3)
C4 O2 C7 O1 9.4(3)
C3 O1 C7 O2 -10.6(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139104828
