#------------------------------------------------------------------------------
#$Date: 2015-06-09 03:59:24 +0300 (Tue, 09 Jun 2015) $
#$Revision: 138945 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/21/7112159.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_7112159
loop_
_publ_author_name
'Tran, Ngon T.'
'Wilson, Sean O.'
'Franz, Annaliese K.'
_publ_section_title
;
 Supramolecular hydrogen-bonding assembly of silanediols with bifunctional
 heterocycles
;
_journal_name_full               Chem.Commun.
_journal_page_first              3738
_journal_paper_doi               10.1039/C4CC00672K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C18 H24 O2 Si, 0.5(C10 H8 N2), C H2 Cl2'
_chemical_formula_sum            'C24 H30 Cl2 N O2 Si'
_chemical_formula_weight         463.48
_chemical_name_common
'dimesitylsilanediol with 4,4'-dipyridyl solvate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-09-01 # Formatted by publCIF
;
_cell_angle_alpha                99.002(18)
_cell_angle_beta                 98.19(2)
_cell_angle_gamma                108.44(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4628(15)
_cell_length_b                   12.198(3)
_cell_length_c                   12.589(2)
_cell_measurement_reflns_used    7694
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.0
_cell_volume                     1191.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8841
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.8832
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         5204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.6524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                4543
_reflns_number_total             5204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc00672k2.cif
_cod_data_source_block           a3
_cod_original_cell_volume        1191.9(4)
_cod_database_code               7112159
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Si1 Si 0.31146(5) 0.37231(3) 0.56724(3) 0.01434(10) Uani 1 1 d
O1 O 0.49186(13) 0.35765(9) 0.54563(8) 0.0172(2) Uani 1 1 d
H1 H 0.560(3) 0.3746(19) 0.6054(19) 0.038(6) Uiso 1 1 d
O2 O 0.32900(14) 0.51109(9) 0.58468(9) 0.0199(2) Uani 1 1 d
H2 H 0.372(3) 0.546(2) 0.5461(19) 0.039(6) Uiso 1 1 d
C1 C 0.13372(17) 0.28876(12) 0.44416(11) 0.0160(3) Uani 1 1 d
C2 C -0.02925(18) 0.29483(13) 0.45129(12) 0.0184(3) Uani 1 1 d
C3 C -0.16504(19) 0.24463(14) 0.36109(13) 0.0217(3) Uani 1 1 d
H3 H -0.270(3) 0.2521(17) 0.3687(15) 0.025(5) Uiso 1 1 d
C4 C -0.14671(19) 0.18702(13) 0.26195(12) 0.0217(3) Uani 1 1 d
C5 C 0.01220(19) 0.17866(13) 0.25518(12) 0.0197(3) Uani 1 1 d
H5 H 0.028(2) 0.1370(16) 0.1848(15) 0.022(4) Uiso 1 1 d
C6 C 0.15216(18) 0.22879(12) 0.34341(12) 0.0172(3) Uani 1 1 d
C7 C 0.31969(19) 0.21932(14) 0.32363(13) 0.0208(3) Uani 1 1 d
H7A H 0.394(3) 0.2946(19) 0.3239(17) 0.033(5) Uiso 1 1 d
H7B H 0.302(2) 0.1669(17) 0.2521(16) 0.028(5) Uiso 1 1 d
H7C H 0.370(3) 0.1888(18) 0.3799(17) 0.031(5) Uiso 1 1 d
C8 C -0.2954(2) 0.13531(17) 0.16477(15) 0.0306(4) Uani 1 1 d
H8A H -0.264(3) 0.099(2) 0.100(2) 0.054(7) Uiso 1 1 d
H8B H -0.385(3) 0.071(2) 0.177(2) 0.059(7) Uiso 1 1 d
H8C H -0.340(3) 0.195(2) 0.148(2) 0.051(7) Uiso 1 1 d
C9 C -0.0640(2) 0.35606(15) 0.55474(13) 0.0228(3) Uani 1 1 d
H9A H -0.183(3) 0.345(2) 0.547(2) 0.051(7) Uiso 1 1 d
H9B H -0.008(3) 0.435(3) 0.571(2) 0.061(8) Uiso 1 1 d
H9C H -0.019(3) 0.337(2) 0.617(2) 0.050(7) Uiso 1 1 d
C10 C 0.27770(17) 0.32088(12) 0.69899(11) 0.0161(3) Uani 1 1 d
C11 C 0.24147(17) 0.19898(13) 0.69779(12) 0.0185(3) Uani 1 1 d
C12 C 0.23353(19) 0.15796(14) 0.79514(13) 0.0226(3) Uani 1 1 d
H12 H 0.215(2) 0.0798(18) 0.7931(15) 0.025(5) Uiso 1 1 d
C13 C 0.25914(19) 0.23378(15) 0.89588(13) 0.0243(3) Uani 1 1 d
C14 C 0.2945(2) 0.35296(15) 0.89728(13) 0.0228(3) Uani 1 1 d
H14 H 0.312(2) 0.4081(17) 0.9665(16) 0.027(5) Uiso 1 1 d
C15 C 0.30561(18) 0.39805(13) 0.80186(12) 0.0192(3) Uani 1 1 d
C16 C 0.3543(2) 0.53071(14) 0.81632(13) 0.0261(3) Uani 1 1 d
H16A H 0.360(3) 0.5644(18) 0.8910(18) 0.036(5) Uiso 1 1 d
H16B H 0.271(3) 0.5553(18) 0.7685(18) 0.037(5) Uiso 1 1 d
H16C H 0.469(3) 0.5674(19) 0.7959(17) 0.036(5) Uiso 1 1 d
C17 C 0.2518(3) 0.1880(2) 1.00065(16) 0.0353(4) Uani 1 1 d
H17A H 0.163(4) 0.118(3) 0.992(2) 0.067(8) Uiso 1 1 d
H17B H 0.242(4) 0.245(3) 1.057(2) 0.070(9) Uiso 1 1 d
H17C H 0.350(4) 0.170(3) 1.022(2) 0.075(9) Uiso 1 1 d
C18 C 0.2110(2) 0.10876(14) 0.59294(13) 0.0237(3) Uani 1 1 d
H18A H 0.302(3) 0.1291(18) 0.5544(17) 0.031(5) Uiso 1 1 d
H18B H 0.204(2) 0.0314(17) 0.6078(15) 0.025(5) Uiso 1 1 d
H18C H 0.109(3) 0.1041(19) 0.5424(18) 0.039(6) Uiso 1 1 d
N21 N 0.71015(15) 0.41708(11) 0.74248(10) 0.0195(3) Uani 1 1 d
C21 C 0.8433(2) 0.51854(14) 0.76974(13) 0.0244(3) Uani 1 1 d
H21 H 0.863(2) 0.5687(18) 0.7147(16) 0.030(5) Uiso 1 1 d
C22 C 0.9581(2) 0.55477(14) 0.86954(13) 0.0247(3) Uani 1 1 d
H22 H 1.049(3) 0.6292(19) 0.8828(17) 0.036(5) Uiso 1 1 d
C23 C 0.93913(17) 0.48290(12) 0.94620(11) 0.0170(3) Uani 1 1 d
C24 C 0.80003(19) 0.37766(13) 0.91732(12) 0.0211(3) Uani 1 1 d
H24 H 0.780(2) 0.3232(17) 0.9640(16) 0.027(5) Uiso 1 1 d
C25 C 0.68978(19) 0.34923(14) 0.81670(13) 0.0225(3) Uani 1 1 d
H25 H 0.591(3) 0.2757(18) 0.7976(16) 0.032(5) Uiso 1 1 d
C31 C 0.8149(2) 0.09809(18) 0.72894(16) 0.0337(4) Uani 1 1 d
H31A H 0.885(3) 0.179(2) 0.7352(18) 0.043(6) Uiso 1 1 d
H31B H 0.865(3) 0.040(2) 0.6953(19) 0.045(6) Uiso 1 1 d
Cl31 Cl 0.78189(6) 0.07820(4) 0.86127(4) 0.03733(12) Uani 1 1 d
Cl32 Cl 0.62259(6) 0.07093(5) 0.63680(4) 0.04362(14) Uani 1 1 d
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
_geom_angle_site_symmetry_3
O2 Si1 O1 109.80(6) .
O2 Si1 C10 108.99(6) .
O1 Si1 C10 105.67(6) .
O2 Si1 C1 107.20(6) .
O1 Si1 C1 110.56(6) .
C10 Si1 C1 114.58(6) .
Si1 O1 H1 109.8(15) .
Si1 O2 H2 117.2(18) .
C6 C1 C2 117.63(13) .
C6 C1 Si1 125.67(11) .
C2 C1 Si1 116.52(11) .
C3 C2 C1 120.67(14) .
C3 C2 C9 117.07(13) .
C1 C2 C9 122.26(13) .
C4 C3 C2 121.77(14) .
C4 C3 H3 120.2(12) .
C2 C3 H3 118.0(12) .
C3 C4 C5 117.81(13) .
C3 C4 C8 120.66(15) .
C5 C4 C8 121.53(15) .
C4 C5 C6 122.21(14) .
C4 C5 H5 119.3(10) .
C6 C5 H5 118.5(11) .
C5 C6 C1 119.89(13) .
C5 C6 C7 117.05(13) .
C1 C6 C7 123.02(13) .
C6 C7 H7A 108.8(13) .
C6 C7 H7B 109.8(11) .
H7A C7 H7B 109.3(17) .
C6 C7 H7C 111.3(12) .
H7A C7 H7C 108.6(17) .
H7B C7 H7C 109.0(17) .
C4 C8 H8A 112.0(15) .
C4 C8 H8B 112.8(16) .
H8A C8 H8B 102(2) .
C4 C8 H8C 110.3(15) .
H8A C8 H8C 110(2) .
H8B C8 H8C 109(2) .
C2 C9 H9A 110.6(14) .
C2 C9 H9B 112.9(17) .
H9A C9 H9B 107(2) .
C2 C9 H9C 113.4(15) .
H9A C9 H9C 114(2) .
H9B C9 H9C 99(2) .
C11 C10 C15 117.53(13) .
C11 C10 Si1 117.97(11) .
C15 C10 Si1 124.08(11) .
C12 C11 C10 120.46(14) .
C12 C11 C18 117.44(14) .
C10 C11 C18 122.10(13) .
C13 C12 C11 121.88(15) .
C13 C12 H12 118.9(12) .
C11 C12 H12 119.1(12) .
C14 C13 C12 117.78(14) .
C14 C13 C17 121.03(16) .
C12 C13 C17 121.18(16) .
C13 C14 C15 122.21(15) .
C13 C14 H14 119.7(11) .
C15 C14 H14 118.1(11) .
C14 C15 C10 120.13(14) .
C14 C15 C16 116.57(14) .
C10 C15 C16 123.27(13) .
C15 C16 H16A 109.1(13) .
C15 C16 H16B 113.3(12) .
H16A C16 H16B 107.8(17) .
C15 C16 H16C 111.4(12) .
H16A C16 H16C 109.5(18) .
H16B C16 H16C 105.6(17) .
C13 C17 H17A 112.9(18) .
C13 C17 H17B 110.0(18) .
H17A C17 H17B 109(2) .
C13 C17 H17C 110.2(19) .
H17A C17 H17C 105(2) .
H17B C17 H17C 110(3) .
C11 C18 H18A 112.5(12) .
C11 C18 H18B 111.6(11) .
H18A C18 H18B 104.9(16) .
C11 C18 H18C 110.3(13) .
H18A C18 H18C 105.9(17) .
H18B C18 H18C 111.5(17) .
C25 N21 C21 117.04(13) .
N21 C21 C22 123.25(14) .
N21 C21 H21 118.3(12) .
C22 C21 H21 118.4(12) .
C21 C22 C23 119.80(14) .
C21 C22 H22 117.9(13) .
C23 C22 H22 122.3(13) .
C24 C23 C22 116.57(13) .
C24 C23 C23 121.66(16) 2_767
C22 C23 C23 121.77(16) 2_767
C25 C24 C23 119.88(14) .
C25 C24 H24 118.3(12) .
C23 C24 H24 121.8(12) .
N21 C25 C24 123.43(14) .
N21 C25 H25 117.2(12) .
C24 C25 H25 119.4(12) .
Cl32 C31 Cl31 112.03(10) .
Cl32 C31 H31A 107.7(14) .
Cl31 C31 H31A 108.3(14) .
Cl32 C31 H31B 105.2(13) .
Cl31 C31 H31B 110.7(13) .
H31A C31 H31B 112.9(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 O2 1.6283(12) .
Si1 O1 1.6470(11) .
Si1 C10 1.8904(15) .
Si1 C1 1.8904(16) .
O1 H1 0.83(2) .
O2 H2 0.75(2) .
C1 C6 1.417(2) .
C1 C2 1.419(2) .
C2 C3 1.397(2) .
C2 C9 1.511(2) .
C3 C4 1.388(2) .
C3 H3 0.94(2) .
C4 C5 1.394(2) .
C4 C8 1.515(2) .
C5 C6 1.402(2) .
C5 H5 1.000(19) .
C6 C7 1.510(2) .
C7 H7A 0.93(2) .
C7 H7B 0.98(2) .
C7 H7C 0.96(2) .
C8 H8A 0.97(3) .
C8 H8B 0.95(3) .
C8 H8C 0.96(3) .
C9 H9A 0.96(3) .
C9 H9B 0.90(3) .
C9 H9C 0.92(3) .
C10 C11 1.417(2) .
C10 C15 1.418(2) .
C11 C12 1.397(2) .
C11 C18 1.513(2) .
C12 C13 1.392(2) .
C12 H12 0.91(2) .
C13 C14 1.385(2) .
C13 C17 1.512(2) .
C14 C15 1.400(2) .
C14 H14 0.97(2) .
C15 C16 1.512(2) .
C16 H16A 0.95(2) .
C16 H16B 1.01(2) .
C16 H16C 1.02(2) .
C17 H17A 0.92(3) .
C17 H17B 0.95(3) .
C17 H17C 0.94(3) .
C18 H18A 0.95(2) .
C18 H18B 0.977(19) .
C18 H18C 0.98(2) .
N21 C25 1.336(2) .
N21 C21 1.339(2) .
C21 C22 1.387(2) .
C21 H21 0.99(2) .
C22 C23 1.395(2) .
C22 H22 0.96(2) .
C23 C24 1.394(2) .
C23 C23 1.491(3) 2_767
C24 C25 1.384(2) .
C24 H24 0.95(2) .
C25 H25 0.98(2) .
C31 Cl32 1.7619(19) .
C31 Cl31 1.769(2) .
C31 H31A 0.96(2) .
C31 H31B 1.01(2) .
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_site_symmetry_A
O2 H2 O1 0.75(2) 2.00(2) 2.7476(16) 174(2) 2_666
O1 H1 N21 0.83(2) 1.88(2) 2.7138(18) 178(2) .
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
O2 Si1 C1 C6 115.20(12) . .
O1 Si1 C1 C6 -4.46(14) . .
C10 Si1 C1 C6 -123.72(12) . .
O2 Si1 C1 C2 -59.74(12) . .
O1 Si1 C1 C2 -179.40(10) . .
C10 Si1 C1 C2 61.33(12) . .
C6 C1 C2 C3 -0.9(2) . .
Si1 C1 C2 C3 174.44(11) . .
C6 C1 C2 C9 179.74(13) . .
Si1 C1 C2 C9 -4.89(18) . .
C1 C2 C3 C4 0.2(2) . .
C9 C2 C3 C4 179.59(14) . .
C2 C3 C4 C5 1.1(2) . .
C2 C3 C4 C8 -178.88(15) . .
C3 C4 C5 C6 -1.7(2) . .
C8 C4 C5 C6 178.26(14) . .
C4 C5 C6 C1 1.0(2) . .
C4 C5 C6 C7 -176.75(14) . .
C2 C1 C6 C5 0.3(2) . .
Si1 C1 C6 C5 -174.57(10) . .
C2 C1 C6 C7 177.95(13) . .
Si1 C1 C6 C7 3.1(2) . .
O2 Si1 C10 C11 173.50(10) . .
O1 Si1 C10 C11 -68.56(12) . .
C1 Si1 C10 C11 53.41(13) . .
O2 Si1 C10 C15 -14.15(14) . .
O1 Si1 C10 C15 103.80(12) . .
C1 Si1 C10 C15 -134.23(12) . .
C15 C10 C11 C12 0.2(2) . .
Si1 C10 C11 C12 173.06(11) . .
C15 C10 C11 C18 -179.47(13) . .
Si1 C10 C11 C18 -6.61(19) . .
C10 C11 C12 C13 0.5(2) . .
C18 C11 C12 C13 -179.80(14) . .
C11 C12 C13 C14 -0.5(2) . .
C11 C12 C13 C17 -179.37(15) . .
C12 C13 C14 C15 -0.3(2) . .
C17 C13 C14 C15 178.59(15) . .
C13 C14 C15 C10 1.0(2) . .
C13 C14 C15 C16 -176.81(15) . .
C11 C10 C15 C14 -1.0(2) . .
Si1 C10 C15 C14 -173.34(11) . .
C11 C10 C15 C16 176.75(14) . .
Si1 C10 C15 C16 4.4(2) . .
C25 N21 C21 C22 0.1(2) . .
N21 C21 C22 C23 1.2(3) . .
C21 C22 C23 C24 -1.3(2) . .
C21 C22 C23 C23 178.99(17) . 2_767
C22 C23 C24 C25 0.2(2) . .
C23 C23 C24 C25 179.89(17) 2_767 .
C21 N21 C25 C24 -1.3(2) . .
C23 C24 C25 N21 1.2(2) . .
