#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/24/2102495.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_2102495
loop_
_publ_author_name
'Turkington, David E.'
'Lough, Alan J.'
'Ferguson, George'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen-bonded adducts of triphenylsilanol with diamines: a finite
 ten-molecule aggregate, and chain, sheet and framework structures
 built from O---H···O,
 O---H···N and
 C---H···π(arene) hydrogen bonds
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              238
_journal_page_last               248
_journal_paper_doi               10.1107/S0108768104002344
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         '2(C18 H16 O Si), C6 H14 N2'
_chemical_formula_sum            'C42 H46 N2 O2 Si2'
_chemical_formula_weight         666.98
_chemical_name_systematic
;
Triphenylsilanol--N,N'-dimethylpiperazine (2/1)
;
_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                 117.868(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.6528(10)
_cell_length_b                   8.1361(4)
_cell_length_c                   16.7852(10)
_cell_measurement_reflns_used    3291
_cell_measurement_temperature    150.0(10)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.75
_cell_volume                     1769.00(19)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD server software (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material
'SHELXL-97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150.0(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Kappa-CCD
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0987
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15411
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.398
_refine_ls_extinction_coef       0.011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0714P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                2276
_reflns_number_total             3291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na5012.cif
_cod_data_source_block           III
_cod_depositor_comments
;

2019-10-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1769.00(18)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_moiety     'C18 H16 O Si, 0.5(C6 H14 N2)'
_cod_original_formula_sum        'C21 H23 N O Si'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     333.49
_cod_database_code               2102495
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_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_type_symbol
Si1 0.75554(5) 0.84180(7) 0.53089(4) 0.0313(2) Uani d . 1 Si
O1 0.71129(13) 0.77748(18) 0.59784(11) 0.0377(4) Uani d . 1 O
C11 0.79164(17) 0.6738(2) 0.47673(16) 0.0323(5) Uani d . 1 C
C12 0.85027(18) 0.5440(3) 0.52875(17) 0.0389(6) Uani d . 1 C
C13 0.88142(19) 0.4214(3) 0.49045(18) 0.0451(6) Uani d . 1 C
C14 0.8558(2) 0.4267(3) 0.40022(19) 0.0463(7) Uani d . 1 C
C15 0.7982(2) 0.5520(3) 0.34725(18) 0.0437(6) Uani d . 1 C
C16 0.76619(18) 0.6739(3) 0.38579(16) 0.0371(6) Uani d . 1 C
C21 0.87396(17) 0.9627(2) 0.60015(15) 0.0302(5) Uani d . 1 C
C22 0.87587(19) 1.0727(3) 0.66397(15) 0.0385(6) Uani d . 1 C
C23 0.9627(2) 1.1639(3) 0.71579(17) 0.0451(6) Uani d . 1 C
C24 1.0503(2) 1.1485(3) 0.70511(17) 0.0438(6) Uani d . 1 C
C25 1.04989(19) 1.0430(3) 0.64162(17) 0.0404(6) Uani d . 1 C
C26 0.96331(17) 0.9509(3) 0.58995(16) 0.0346(5) Uani d . 1 C
C31 0.65816(17) 0.9741(3) 0.44083(15) 0.0324(5) Uani d . 1 C
C32 0.55277(18) 0.9617(3) 0.41415(17) 0.0403(6) Uani d . 1 C
C33 0.4805(2) 1.0508(3) 0.34309(18) 0.0485(7) Uani d . 1 C
C34 0.5120(2) 1.1564(3) 0.29671(17) 0.0479(7) Uani d . 1 C
C35 0.6158(2) 1.1749(3) 0.32381(17) 0.0452(6) Uani d . 1 C
C36 0.68803(19) 1.0854(3) 0.39457(16) 0.0391(6) Uani d . 1 C
N1 0.60535(15) 0.4909(2) 0.57194(13) 0.0369(5) Uani d . 1 N
C1 0.57249(19) 0.4123(3) 0.48410(16) 0.0404(6) Uani d . 1 C
C2 0.51628(18) 0.5000(3) 0.58999(16) 0.0384(6) Uani d . 1 C
C3 0.6892(2) 0.4008(3) 0.64375(18) 0.0487(7) Uani d . 1 C
H1 0.6768 0.6913 0.5767 0.057 Uiso calc R 1 H
H12 0.8691 0.5396 0.5911 0.047 Uiso calc R 1 H
H13 0.9210 0.3320 0.5265 0.054 Uiso calc R 1 H
H14 0.8787 0.3419 0.3750 0.056 Uiso calc R 1 H
H15 0.7803 0.5557 0.2851 0.052 Uiso calc R 1 H
H16 0.7252 0.7612 0.3488 0.045 Uiso calc R 1 H
H22 0.8163 1.0853 0.6721 0.037(6) Uiso calc R 1 H
H23 0.9625 1.2382 0.7593 0.052(7) Uiso calc R 1 H
H24 1.1104 1.2108 0.7416 0.056(8) Uiso calc R 1 H
H25 1.1094 1.0331 0.6331 0.047(7) Uiso calc R 1 H
H26 0.9642 0.8775 0.5463 0.040(7) Uiso calc R 1 H
H32 0.5304 0.8896 0.4460 0.046(7) Uiso calc R 1 H
H33 0.4092 1.0395 0.3261 0.068(9) Uiso calc R 1 H
H34 0.4625 1.2161 0.2464 0.062(8) Uiso calc R 1 H
H35 0.6377 1.2506 0.2931 0.052(7) Uiso calc R 1 H
H36 0.7593 1.0997 0.4121 0.054(8) Uiso calc R 1 H
H1A 0.5523 0.2972 0.4870 0.046(7) Uiso calc R 1 H
H1B 0.6313 0.4101 0.4704 0.050(7) Uiso calc R 1 H
H2A 0.5368 0.5585 0.6476 0.051(7) Uiso calc R 1 H
H2B 0.4947 0.3874 0.5961 0.047(7) Uiso calc R 1 H
H3A 0.6665 0.2887 0.6465 0.071(9) Uiso calc R 1 H
H3B 0.7092 0.4562 0.7014 0.048(7) Uiso calc R 1 H
H3C 0.7486 0.3969 0.6318 0.065(9) Uiso calc R 1 H
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
O1 Si1 C11 . . 113.59(9) no
O1 Si1 C21 . . 107.23(9) no
C11 Si1 C21 . . 107.52(10) no
O1 Si1 C31 . . 110.24(10) no
C11 Si1 C31 . . 108.35(10) no
C21 Si1 C31 . . 109.85(9) no
Si1 O1 H1 . . 109.5 no
C12 C11 C16 . . 117.5(2) no
C12 C11 Si1 . . 119.30(18) no
C16 C11 Si1 . . 123.16(17) no
C13 C12 C11 . . 120.2(2) no
C13 C12 H12 . . 119.9 no
C11 C12 H12 . . 119.9 no
C12 C13 C14 . . 120.7(2) no
C12 C13 H13 . . 119.7 no
C14 C13 H13 . . 119.7 no
C15 C14 C13 . . 120.7(2) no
C15 C14 H14 . . 119.7 no
C13 C14 H14 . . 119.7 no
C14 C15 C16 . . 118.4(2) no
C14 C15 H15 . . 120.8 no
C16 C15 H15 . . 120.8 no
C15 C16 C11 . . 122.6(2) no
C15 C16 H16 . . 118.7 no
C11 C16 H16 . . 118.7 no
C22 C21 C26 . . 117.2(2) no
C22 C21 Si1 . . 120.10(17) no
C26 C21 Si1 . . 122.73(17) no
C23 C22 C21 . . 121.0(2) no
C23 C22 H22 . . 119.5 no
C21 C22 H22 . . 119.5 no
C22 C23 C24 . . 120.7(2) no
C22 C23 H23 . . 119.7 no
C24 C23 H23 . . 119.7 no
C25 C24 C23 . . 119.5(2) no
C25 C24 H24 . . 120.3 no
C23 C24 H24 . . 120.3 no
C24 C25 C26 . . 120.0(2) no
C24 C25 H25 . . 120.0 no
C26 C25 H25 . . 120.0 no
C25 C26 C21 . . 121.6(2) no
C25 C26 H26 . . 119.2 no
C21 C26 H26 . . 119.2 no
C36 C31 C32 . . 117.2(2) no
C36 C31 Si1 . . 120.56(17) no
C32 C31 Si1 . . 122.13(18) no
C33 C32 C31 . . 121.9(2) no
C33 C32 H32 . . 119.1 no
C31 C32 H32 . . 119.1 no
C32 C33 C34 . . 119.6(2) no
C32 C33 H33 . . 120.2 no
C34 C33 H33 . . 120.2 no
C33 C34 C35 . . 119.5(2) no
C33 C34 H34 . . 120.3 no
C35 C34 H34 . . 120.3 no
C36 C35 C34 . . 120.9(2) no
C36 C35 H35 . . 119.6 no
C34 C35 H35 . . 119.6 no
C35 C36 C31 . . 120.8(2) no
C35 C36 H36 . . 119.6 no
C31 C36 H36 . . 119.6 no
C3 N1 C1 . . 111.52(19) no
C3 N1 C2 . . 109.98(19) no
C1 N1 C2 . . 108.83(18) no
N1 C1 C2 . 3_666 112.16(19) no
N1 C1 H1A . . 109.2 no
C2 C1 H1A 3_666 . 109.2 no
N1 C1 H1B . . 109.2 no
C2 C1 H1B 3_666 . 109.2 no
H1A C1 H1B . . 107.9 no
N1 C2 C1 . 3_666 111.3(2) no
N1 C2 H2A . . 109.4 no
C1 C2 H2A 3_666 . 109.4 no
N1 C2 H2B . . 109.4 no
C1 C2 H2B 3_666 . 109.4 no
H2A C2 H2B . . 108.0 no
N1 C3 H3A . . 109.5 no
N1 C3 H3B . . 109.5 no
H3A C3 H3B . . 109.5 no
N1 C3 H3C . . 109.5 no
H3A C3 H3C . . 109.5 no
H3B C3 H3C . . 109.5 no
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 O1 . 1.6242(16) no
Si1 C11 . 1.850(2) no
Si1 C21 . 1.856(2) no
Si1 C31 . 1.861(2) no
O1 H1 . 0.84 no
C11 C12 . 1.384(3) no
C11 C16 . 1.392(3) no
C12 C13 . 1.375(3) no
C12 H12 . 0.95 no
C13 C14 . 1.380(4) no
C13 H13 . 0.95 no
C14 C15 . 1.356(3) no
C14 H14 . 0.95 no
C15 C16 . 1.380(3) no
C15 H15 . 0.95 no
C16 H16 . 0.95 no
C21 C22 . 1.386(3) no
C21 C26 . 1.401(3) no
C22 C23 . 1.376(3) no
C22 H22 . 0.95 no
C23 C24 . 1.382(4) no
C23 H23 . 0.95 no
C24 C25 . 1.366(3) no
C24 H24 . 0.95 no
C25 C26 . 1.376(3) no
C25 H25 . 0.95 no
C26 H26 . 0.95 no
C31 C36 . 1.390(3) no
C31 C32 . 1.396(3) no
C32 C33 . 1.374(3) no
C32 H32 . 0.95 no
C33 C34 . 1.376(4) no
C33 H33 . 0.95 no
C34 C35 . 1.378(4) no
C34 H34 . 0.95 no
C35 C36 . 1.373(3) no
C35 H35 . 0.95 no
C36 H36 . 0.95 no
N1 C3 . 1.454(3) no
N1 C1 . 1.467(3) no
N1 C2 . 1.473(3) no
C1 C2 3_666 1.495(3) no
C1 H1A . 0.99 no
C1 H1B . 0.99 no
C2 C1 3_666 1.495(3) no
C2 H2A . 0.99 no
C2 H2B . 0.99 no
C3 H3A . 0.98 no
C3 H3B . 0.98 no
C3 H3C . 0.98 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.92 2.721(2) 159 y
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_4
_geom_torsion
_geom_torsion_publ_flag
O1 Si1 C11 C12 . -46.8(2) no
C21 Si1 C11 C12 . 71.71(19) no
C31 Si1 C11 C12 . -169.61(17) no
O1 Si1 C11 C16 . 135.91(19) no
C21 Si1 C11 C16 . -105.62(19) no
C31 Si1 C11 C16 . 13.1(2) no
C16 C11 C12 C13 . 0.1(3) no
Si1 C11 C12 C13 . -177.36(18) no
C11 C12 C13 C14 . 0.7(4) no
C12 C13 C14 C15 . -0.9(4) no
C13 C14 C15 C16 . 0.2(4) no
C14 C15 C16 C11 . 0.7(4) no
C12 C11 C16 C15 . -0.8(3) no
Si1 C11 C16 C15 . 176.55(18) no
O1 Si1 C21 C22 . -42.9(2) no
C11 Si1 C21 C22 . -165.43(18) no
C31 Si1 C21 C22 . 76.9(2) no
O1 Si1 C21 C26 . 138.36(18) no
C11 Si1 C21 C26 . 15.9(2) no
C31 Si1 C21 C26 . -101.85(19) no
C26 C21 C22 C23 . -1.0(3) no
Si1 C21 C22 C23 . -179.78(17) no
C21 C22 C23 C24 . 0.3(4) no
C22 C23 C24 C25 . 0.8(4) no
C23 C24 C25 C26 . -1.1(4) no
C24 C25 C26 C21 . 0.4(3) no
C22 C21 C26 C25 . 0.7(3) no
Si1 C21 C26 C25 . 179.43(17) no
O1 Si1 C31 C36 . 158.60(17) no
C11 Si1 C31 C36 . -76.5(2) no
C21 Si1 C31 C36 . 40.7(2) no
O1 Si1 C31 C32 . -24.2(2) no
C11 Si1 C31 C32 . 100.69(19) no
C21 Si1 C31 C32 . -142.13(18) no
C36 C31 C32 C33 . 2.3(3) no
Si1 C31 C32 C33 . -174.98(18) no
C31 C32 C33 C34 . -0.4(4) no
C32 C33 C34 C35 . -1.8(4) no
C33 C34 C35 C36 . 2.1(4) no
C34 C35 C36 C31 . -0.2(4) no
C32 C31 C36 C35 . -2.0(3) no
Si1 C31 C36 C35 . 175.34(18) no
C3 N1 C1 C2 3_666 177.9(2) no
C2 N1 C1 C2 3_666 56.4(3) no
C3 N1 C2 C1 3_666 -178.35(19) no
C1 N1 C2 C1 3_666 -55.9(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139063545
