# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

data_a1b


_publ_section_references         
;
((1)A short history of SHELX, George M. Sheldrick, Acta Cryst. (2008).
A64, 112-122 References:

(2) Bruker (2002). SMART (Version 5.054) Bruker (2004) SMART APEX
(Version 1.2.1.21) and SAINT (Version 7.23a). Bruker AXS Inc., Madison,
Wisconsin, USA.

(3) An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

(4) Sheldrick, G.M., SADABS (2003). Version 2.10, 'Siemens Area Detector
Absorption Correction' Universitat Gottingen: Gottingen, Germany.

(5) Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

(6) Sheldrick, G. M., (1997). SHELXS97 and SHELXL97. Universitat
Gottingen: Gottingen, Germany.

(7) On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

(8) Sheldrick, G. M., (2008). SHELXS97 and SHELXL97. Acta Cryst.
A64, 112-122. 8.

(9) Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann,
H., OLEX2: A complete structure solution, refinement and analysis
program (2009). J. Appl. Cryst., 42, 339-341.

(10) Hooft, R.W.W, Straver, L.H. & Spek,A.L. (2008). J. Appl, Cryst. 41,
96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron
;
#Added by publCIF




_publ_section_acknowledgements   
;
The authors gratefully acknowledge UC Davis, 3M Corporation, National Science
Foundation (CHE-0847358), UC Davis Bradford Borge Fellowship,Achievement
Rewards for College Scientists Scholarship(ARCS),and the U.S. Department of
Education Graduate Assistance in Areas of National Need (GAANN) Fellowship. We
thank the National Science Foundation (#0840444) for the Bruker AXS Dual
source diffractometer.
;
#Added by publCIF




_publ_section_synopsis           .
#Added by publCIF




_publ_section_keywords           
;
Cooperative hydrogen bonding, silanediol, self-association
;

#Added by publCIF



_publ_section_related_literature ?

_publ_contact_author_name        'Ngon T. Tran'

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;


_publ_requested_category         ?

_publ_requested_journal          ?

_publ_contact_author_fax         530-752-8995

_publ_contact_author_phone       530-752-9820

_publ_contact_author_email       akfranz@ucdavis.edu

_publ_contact_author_address     
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;


# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Tran, Ngon T.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Wilson, Sean O.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Franz, Annaliese K.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. ?




_publ_section_abstract           
;
The structure of dimesitylsilanediol with 7-azaindole,
C₁₈H₂₄O₂Si.C₇H₆N₂, at 90 K has monoclinic (P2₁/c)
symmetry. It is of interest with respect to catalysis. The structure displays
O---H...N, O---H...O, N---H...O hydrogen bonding. Contact distances are given.
;


_publ_section_title              
;
X-ray Crystallographic and NMR Studies of Silanediol Hydrogen-bonding Patterns
with Bifunctional Lewis Bases
;
#Added by publCIF



_audit_update_record             
;
2013-09-01 # Formatted by publCIF

;

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents


section
;
Introduction
;
;

;
section
;
Experimental
;
;
A suitable crystal was mounted on a glass fiber with silicone grease and placed
in the cold dinitrogen stream of a Bruker SMART diffractometer with Mo
Ka radiation at 90((22)) K.
;
subsection
;
Synthesis and crystallization
;
;
Crystals were grown from slow evaporation of solution that contained 1:1
mixture of dimesitylsilanediol and 7-azaindole in benzene. A suitable crystal
was mounted on a glass fiber with silicone grease and placed in the cold
dinitrogen stream of a Bruker SMART diffractometer with Mo Ka radiation
at 90((22)) K.
;
subsection
;
Refinement
;
;
Crystal data, data collection and structure refinement details are summarized
in Table 1. Structures were solved by direct methods and refined using all
data. All protons were located from a difference-Fourier map after all
non-hydrogen atoms were refined anisotropically several times. Positions and
thermal parameters were allowed to refine freely (xyzU).
;
section
;
Results and discussion
;
;

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            'dimesitylsilanediol with 7-azaindole'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 O2 Si, C7 H6 N2'
_chemical_formula_sum            'C25 H30 N2 O2 Si'
_chemical_formula_weight         418.60

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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'

_cell_length_a                   11.9457(10)
_cell_length_b                   11.0271(10)
_cell_length_c                   17.2592(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9210(10)
_cell_angle_gamma                90.00
_cell_volume                     2251.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9424
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23897
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.51
_reflns_number_total             5185
_reflns_number_gt                4384
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.9604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5185
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.83461(3) 0.48582(3) -0.08433(2) 0.01744(11) Uani 1 1 d . . .
O1 O 0.95673(8) 0.42082(9) -0.08894(6) 0.0202(2) Uani 1 1 d . . .
H1 H 0.958(2) 0.340(3) -0.0833(16) 0.078(9) Uiso 1 1 d . . .
O2 O 0.83815(8) 0.54270(9) 0.00422(6) 0.0211(2) Uani 1 1 d . . .
H2 H 0.901(2) 0.541(2) 0.0294(14) 0.054(7) Uiso 1 1 d . . .
C1 C 0.80586(11) 0.61660(12) -0.15404(8) 0.0189(3) Uani 1 1 d . . .
C2 C 0.69887(11) 0.67386(12) -0.15800(8) 0.0214(3) Uani 1 1 d . . .
C3 C 0.66985(12) 0.76817(13) -0.21084(8) 0.0244(3) Uani 1 1 d . . .
H3 H 0.5965(15) 0.8062(16) -0.2116(10) 0.029(4) Uiso 1 1 d . . .
C4 C 0.74289(13) 0.80847(13) -0.26128(8) 0.0256(3) Uani 1 1 d . . .
C5 C 0.84854(12) 0.75414(13) -0.25653(8) 0.0233(3) Uani 1 1 d . . .
H5 H 0.9030(15) 0.7811(17) -0.2896(11) 0.029(4) Uiso 1 1 d . . .
C6 C 0.88153(11) 0.66035(12) -0.20385(8) 0.0209(3) Uani 1 1 d . . .
C7 C 0.99977(12) 0.61038(14) -0.20256(9) 0.0257(3) Uani 1 1 d . . .
H7A H 1.0401(16) 0.6573(18) -0.2370(11) 0.037(5) Uiso 1 1 d . . .
H7B H 1.0436(15) 0.6113(17) -0.1487(12) 0.033(5) Uiso 1 1 d . . .
H7C H 0.9987(17) 0.526(2) -0.2201(12) 0.041(5) Uiso 1 1 d . . .
C8 C 0.70950(18) 0.91071(17) -0.31790(11) 0.0372(4) Uani 1 1 d . . .
H8A H 0.755(2) 0.915(2) -0.3593(15) 0.060(7) Uiso 1 1 d . . .
H8B H 0.635(3) 0.905(3) -0.3413(18) 0.084(9) Uiso 1 1 d . . .
H8C H 0.713(2) 0.985(3) -0.2931(17) 0.080(9) Uiso 1 1 d . . .
C9 C 0.61112(12) 0.63467(14) -0.10767(9) 0.0259(3) Uani 1 1 d . . .
H9A H 0.6443(15) 0.6212(17) -0.0531(11) 0.030(5) Uiso 1 1 d . . .
H9B H 0.5516(17) 0.6997(19) -0.1078(12) 0.043(5) Uiso 1 1 d . . .
H9C H 0.5712(15) 0.5626(18) -0.1285(11) 0.033(5) Uiso 1 1 d . . .
C10 C 0.72375(11) 0.36384(12) -0.10594(8) 0.0191(3) Uani 1 1 d . . .
C11 C 0.70353(11) 0.31778(12) -0.18355(8) 0.0199(3) Uani 1 1 d . . .
C12 C 0.62756(11) 0.22203(13) -0.20179(8) 0.0219(3) Uani 1 1 d . . .
H12 H 0.6164(14) 0.1928(16) -0.2541(10) 0.025(4) Uiso 1 1 d . . .
C13 C 0.57033(11) 0.16835(13) -0.14610(9) 0.0236(3) Uani 1 1 d . . .
C14 C 0.58998(12) 0.21405(13) -0.07006(9) 0.0239(3) Uani 1 1 d . . .
H14 H 0.5502(14) 0.1799(16) -0.0295(10) 0.028(4) Uiso 1 1 d . . .
C15 C 0.66500(11) 0.30930(13) -0.04918(8) 0.0217(3) Uani 1 1 d . . .
C16 C 0.68143(14) 0.34782(16) 0.03597(9) 0.0305(3) Uani 1 1 d . . .
H16A H 0.6368(16) 0.2933(18) 0.0661(11) 0.036(5) Uiso 1 1 d . . .
H16B H 0.7624(18) 0.3447(19) 0.0589(12) 0.043(5) Uiso 1 1 d . . .
H16C H 0.6568(17) 0.430(2) 0.0420(12) 0.046(6) Uiso 1 1 d . . .
C17 C 0.49166(14) 0.06234(15) -0.16570(10) 0.0300(3) Uani 1 1 d . . .
H17A H 0.4140(18) 0.0807(19) -0.1607(12) 0.043(5) Uiso 1 1 d . . .
H17B H 0.4931(18) 0.0343(19) -0.2203(13) 0.043(5) Uiso 1 1 d . . .
H17C H 0.512(2) -0.001(2) -0.1289(14) 0.057(7) Uiso 1 1 d . . .
C18 C 0.76494(13) 0.36473(13) -0.24846(8) 0.0232(3) Uani 1 1 d . . .
H18A H 0.7531(15) 0.3125(17) -0.2938(11) 0.031(5) Uiso 1 1 d . . .
H18B H 0.7388(16) 0.4453(19) -0.2662(11) 0.037(5) Uiso 1 1 d . . .
H18C H 0.8447(16) 0.3713(18) -0.2341(11) 0.035(5) Uiso 1 1 d . . .
N21 N 0.82319(10) 0.80020(12) 0.03988(7) 0.0249(3) Uani 1 1 d . . .
H21 H 0.8211(17) 0.721(2) 0.0258(13) 0.047(6) Uiso 1 1 d . . .
C21 C 0.91768(11) 0.86510(12) 0.06725(8) 0.0206(3) Uani 1 1 d . . .
N22 N 1.02272(10) 0.82076(10) 0.08113(7) 0.0220(2) Uani 1 1 d . . .
C22 C 1.10279(12) 0.90367(14) 0.10417(8) 0.0255(3) Uani 1 1 d . . .
H22 H 1.1823(16) 0.8740(18) 0.1125(11) 0.034(5) Uiso 1 1 d . . .
C23 C 1.08067(14) 1.02510(14) 0.11469(9) 0.0282(3) Uani 1 1 d . . .
H23 H 1.1495(18) 1.082(2) 0.1307(13) 0.049(6) Uiso 1 1 d . . .
C24 C 0.97222(14) 1.06839(14) 0.10314(9) 0.0292(3) Uani 1 1 d . . .
H24 H 0.9546(17) 1.1623(19) 0.1107(12) 0.046(6) Uiso 1 1 d . . .
C25 C 0.88629(13) 0.98731(13) 0.07835(8) 0.0255(3) Uani 1 1 d . . .
C26 C 0.76522(15) 0.99261(15) 0.05601(10) 0.0325(3) Uani 1 1 d . . .
H26 H 0.719(2) 1.059(2) 0.0540(14) 0.054(6) Uiso 1 1 d . . .
C27 C 0.73186(13) 0.87798(15) 0.03268(10) 0.0310(3) Uani 1 1 d . . .
H27 H 0.6572(18) 0.8499(19) 0.0154(12) 0.043(5) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Si1 O1 1.6371(10) . ?
Si1 O2 1.6472(10) . ?
Si1 C1 1.8793(14) . ?
Si1 C10 1.8883(14) . ?
O1 H1 0.90(3) . ?
O2 H2 0.82(2) . ?
C1 C6 1.4153(19) . ?
C1 C2 1.4187(18) . ?
C2 C3 1.395(2) . ?
C2 C9 1.514(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.970(18) . ?
C4 C5 1.389(2) . ?
C4 C8 1.509(2) . ?
C5 C6 1.3974(19) . ?
C5 H5 0.969(18) . ?
C6 C7 1.5134(19) . ?
C7 H7A 0.97(2) . ?
C7 H7B 1.00(2) . ?
C7 H7C 0.98(2) . ?
C8 H8A 0.96(3) . ?
C8 H8B 0.93(3) . ?
C8 H8C 0.92(3) . ?
C9 H9A 0.982(19) . ?
C9 H9B 1.01(2) . ?
C9 H9C 0.97(2) . ?
C10 C15 1.4154(19) . ?
C10 C11 1.4219(18) . ?
C11 C12 1.3995(18) . ?
C11 C18 1.5125(19) . ?
C12 C13 1.387(2) . ?
C12 H12 0.950(18) . ?
C13 C14 1.395(2) . ?
C13 C17 1.5089(19) . ?
C14 C15 1.3955(19) . ?
C14 H14 0.975(18) . ?
C15 C16 1.516(2) . ?
C16 H16A 1.00(2) . ?
C16 H16B 0.99(2) . ?
C16 H16C 0.97(2) . ?
C17 H17A 0.96(2) . ?
C17 H17B 0.99(2) . ?
C17 H17C 0.95(2) . ?
C18 H18A 0.966(19) . ?
C18 H18B 0.98(2) . ?
C18 H18C 0.954(19) . ?
N21 C21 1.3647(18) . ?
N21 C27 1.380(2) . ?
N21 H21 0.90(2) . ?
C21 N22 1.3372(17) . ?
C21 C25 1.4189(19) . ?
N22 C22 1.3432(18) . ?
C22 C23 1.382(2) . ?
C22 H22 0.997(19) . ?
C23 C24 1.369(2) . ?
C23 H23 1.04(2) . ?
C24 C25 1.384(2) . ?
C24 H24 1.07(2) . ?
C25 C26 1.446(2) . ?
C26 C27 1.369(2) . ?
C26 H26 0.91(2) . ?
C27 H27 0.95(2) . ?

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
O1 Si1 O2 107.62(5) . . ?
O1 Si1 C1 112.97(6) . . ?
O2 Si1 C1 106.31(6) . . ?
O1 Si1 C10 106.50(6) . . ?
O2 Si1 C10 112.47(6) . . ?
C1 Si1 C10 111.03(6) . . ?
Si1 O1 H1 115.4(17) . . ?
Si1 O2 H2 113.1(17) . . ?
C6 C1 C2 117.75(12) . . ?
C6 C1 Si1 125.09(10) . . ?
C2 C1 Si1 117.14(10) . . ?
C3 C2 C1 120.28(13) . . ?
C3 C2 C9 117.30(12) . . ?
C1 C2 C9 122.41(12) . . ?
C4 C3 C2 121.85(13) . . ?
C4 C3 H3 119.9(11) . . ?
C2 C3 H3 118.3(11) . . ?
C3 C4 C5 118.00(13) . . ?
C3 C4 C8 120.83(14) . . ?
C5 C4 C8 121.14(15) . . ?
C4 C5 C6 122.00(14) . . ?
C4 C5 H5 120.7(11) . . ?
C6 C5 H5 117.3(11) . . ?
C5 C6 C1 120.07(13) . . ?
C5 C6 C7 117.26(13) . . ?
C1 C6 C7 122.67(12) . . ?
C6 C7 H7A 109.8(11) . . ?
C6 C7 H7B 112.1(11) . . ?
H7A C7 H7B 109.0(15) . . ?
C6 C7 H7C 111.7(12) . . ?
H7A C7 H7C 107.9(17) . . ?
H7B C7 H7C 106.2(16) . . ?
C4 C8 H8A 113.2(15) . . ?
C4 C8 H8B 112.7(19) . . ?
H8A C8 H8B 107(2) . . ?
C4 C8 H8C 111.6(18) . . ?
H8A C8 H8C 108(2) . . ?
H8B C8 H8C 104(3) . . ?
C2 C9 H9A 111.9(10) . . ?
C2 C9 H9B 109.8(12) . . ?
H9A C9 H9B 107.5(16) . . ?
C2 C9 H9C 111.4(11) . . ?
H9A C9 H9C 110.2(15) . . ?
H9B C9 H9C 105.8(15) . . ?
C15 C10 C11 117.66(12) . . ?
C15 C10 Si1 124.55(10) . . ?
C11 C10 Si1 117.65(10) . . ?
C12 C11 C10 120.14(12) . . ?
C12 C11 C18 117.22(12) . . ?
C10 C11 C18 122.60(12) . . ?
C13 C12 C11 122.17(13) . . ?
C13 C12 H12 119.7(10) . . ?
C11 C12 H12 118.1(10) . . ?
C12 C13 C14 117.57(13) . . ?
C12 C13 C17 121.78(13) . . ?
C14 C13 C17 120.63(14) . . ?
C15 C14 C13 122.25(13) . . ?
C15 C14 H14 117.7(10) . . ?
C13 C14 H14 120.1(10) . . ?
C14 C15 C10 120.20(13) . . ?
C14 C15 C16 117.00(13) . . ?
C10 C15 C16 122.78(12) . . ?
C15 C16 H16A 109.2(11) . . ?
C15 C16 H16B 111.4(12) . . ?
H16A C16 H16B 109.5(16) . . ?
C15 C16 H16C 111.5(13) . . ?
H16A C16 H16C 108.6(16) . . ?
H16B C16 H16C 106.5(17) . . ?
C13 C17 H17A 113.3(13) . . ?
C13 C17 H17B 111.2(12) . . ?
H17A C17 H17B 106.9(17) . . ?
C13 C17 H17C 109.0(14) . . ?
H17A C17 H17C 104.8(19) . . ?
H17B C17 H17C 111.4(19) . . ?
C11 C18 H18A 111.3(11) . . ?
C11 C18 H18B 112.1(11) . . ?
H18A C18 H18B 106.5(15) . . ?
C11 C18 H18C 113.8(12) . . ?
H18A C18 H18C 106.6(16) . . ?
H18B C18 H18C 106.0(16) . . ?
C21 N21 C27 108.13(12) . . ?
C21 N21 H21 126.1(13) . . ?
C27 N21 H21 125.6(13) . . ?
N22 C21 N21 125.54(12) . . ?
N22 C21 C25 125.59(13) . . ?
N21 C21 C25 108.87(12) . . ?
C21 N22 C22 114.61(12) . . ?
N22 C22 C23 123.87(14) . . ?
N22 C22 H22 116.4(11) . . ?
C23 C22 H22 119.7(11) . . ?
C24 C23 C22 120.86(14) . . ?
C24 C23 H23 121.7(12) . . ?
C22 C23 H23 117.5(12) . . ?
C23 C24 C25 117.80(14) . . ?
C23 C24 H24 121.2(11) . . ?
C25 C24 H24 120.9(11) . . ?
C24 C25 C21 117.19(14) . . ?
C24 C25 C26 136.76(14) . . ?
C21 C25 C26 106.00(13) . . ?
C27 C26 C25 106.32(14) . . ?
C27 C26 H26 125.7(15) . . ?
C25 C26 H26 127.9(15) . . ?
C26 C27 N21 110.67(14) . . ?
C26 C27 H27 127.9(13) . . ?
N21 C27 H27 121.4(13) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Si1 C1 C6 -2.52(13) . . . . ?
O2 Si1 C1 C6 115.29(11) . . . . ?
C10 Si1 C1 C6 -122.09(11) . . . . ?
O1 Si1 C1 C2 176.03(9) . . . . ?
O2 Si1 C1 C2 -66.16(11) . . . . ?
C10 Si1 C1 C2 56.46(11) . . . . ?
C6 C1 C2 C3 1.39(19) . . . . ?
Si1 C1 C2 C3 -177.26(10) . . . . ?
C6 C1 C2 C9 179.88(12) . . . . ?
Si1 C1 C2 C9 1.22(17) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C9 C2 C3 C4 -178.04(13) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C2 C3 C4 C8 -179.99(14) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
C8 C4 C5 C6 179.23(14) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 -178.49(13) . . . . ?
C2 C1 C6 C5 -2.12(19) . . . . ?
Si1 C1 C6 C5 176.42(10) . . . . ?
C2 C1 C6 C7 177.32(12) . . . . ?
Si1 C1 C6 C7 -4.14(19) . . . . ?
O1 Si1 C10 C15 105.93(12) . . . . ?
O2 Si1 C10 C15 -11.72(13) . . . . ?
C1 Si1 C10 C15 -130.71(11) . . . . ?
O1 Si1 C10 C11 -69.53(11) . . . . ?
O2 Si1 C10 C11 172.83(9) . . . . ?
C1 Si1 C10 C11 53.84(12) . . . . ?
C15 C10 C11 C12 0.18(19) . . . . ?
Si1 C10 C11 C12 175.95(10) . . . . ?
C15 C10 C11 C18 -177.24(12) . . . . ?
Si1 C10 C11 C18 -1.47(17) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C18 C11 C12 C13 177.14(13) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C12 C13 C17 -177.85(13) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C17 C13 C14 C15 177.83(13) . . . . ?
C13 C14 C15 C10 0.5(2) . . . . ?
C13 C14 C15 C16 -178.15(14) . . . . ?
C11 C10 C15 C14 -0.21(19) . . . . ?
Si1 C10 C15 C14 -175.66(10) . . . . ?
C11 C10 C15 C16 178.34(13) . . . . ?
Si1 C10 C15 C16 2.9(2) . . . . ?
C27 N21 C21 N22 -179.48(13) . . . . ?
C27 N21 C21 C25 0.35(16) . . . . ?
N21 C21 N22 C22 176.78(13) . . . . ?
C25 C21 N22 C22 -3.0(2) . . . . ?
C21 N22 C22 C23 1.2(2) . . . . ?
N22 C22 C23 C24 1.2(2) . . . . ?
C22 C23 C24 C25 -1.9(2) . . . . ?
C23 C24 C25 C21 0.3(2) . . . . ?
C23 C24 C25 C26 -176.48(17) . . . . ?
N22 C21 C25 C24 2.3(2) . . . . ?
N21 C21 C25 C24 -177.52(13) . . . . ?
N22 C21 C25 C26 -179.96(14) . . . . ?
N21 C21 C25 C26 0.21(16) . . . . ?
C24 C25 C26 C27 176.36(18) . . . . ?
C21 C25 C26 C27 -0.69(17) . . . . ?
C25 C26 C27 N21 0.93(19) . . . . ?
C21 N21 C27 C26 -0.82(18) . . . . ?

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
O1 H1 N22 0.90(3) 1.79(3) 2.6769(15) 171(3) 3_765
O2 H2 O1 0.82(2) 1.91(2) 2.7049(14) 166(2) 3_765
N21 H21 O2 0.90(2) 2.02(2) 2.9161(16) 172(2) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.054

_database_code_depnum_ccdc_archive 'CCDC 958784'
data_a4


_publ_section_references         
;
(1)A short history of SHELX, George M. Sheldrick, Acta Cryst. (2008).
A64, 112-122 References:

(2) Bruker (2002). SMART (Version 5.054) Bruker (2004) SMART APEX
(Version 1.2.1.21) and SAINT (Version 7.23a). Bruker AXS Inc., Madison,
Wisconsin, USA.

(3) An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

(4) Sheldrick, G.M., SADABS (2003). Version 2.10, 'Siemens Area Detector
Absorption Correction' Universitat Gottingen: Gottingen, Germany.

(5) Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

(6) Sheldrick, G. M., (1997). SHELXS97 and SHELXL97. Universitat
Gottingen: Gottingen, Germany.

(7) On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

(8) Sheldrick, G. M., (2008). SHELXS97 and SHELXL97. Acta Cryst.
A64, 112-122. 8.

(9) Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann,
H., OLEX2: A complete structure solution, refinement and analysis
program (2009). J. Appl. Cryst., 42, 339-341.

(10) Hooft, R.W.W, Straver, L.H. & Spek,A.L. (2008). J. Appl, Cryst. 41,
96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron
;
#Added by publCIF




_publ_section_acknowledgements   
;
The authors gratefully acknowledge UC Davis, 3M Corporation, National Science
Foundation (CHE-0847358), UC Davis Bradford Borge Fellowship,Achievement
Rewards for College Scientists Scholarship(ARCS),and the U.S. Department of
Education Graduate Assistance in Areas of National Need (GAANN) Fellowship. We
thank the National Science Foundation (#0840444) for the Bruker AXS Dual
source diffractometer.
;
#Added by publCIF




_publ_section_synopsis           .
#Added by publCIF




_publ_section_keywords           
;
Cooperative hydrogen bonding, silanediol, self-association
;

#Added by publCIF



_publ_section_related_literature ?

_publ_contact_author_name        'Annaliese K. Franz'

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;


_publ_requested_category         ?

_publ_requested_journal          ?

_publ_contact_author_fax         530-752-8995

_publ_contact_author_phone       530-752-9820

_publ_contact_author_email       akfranz@ucdavis.edu

_publ_contact_author_address     
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616


;


# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Tran, Ngon T.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Wilson, Sean O.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Franz, Annaliese K.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. ?




_publ_section_abstract           
;
The structure of dimesitylsilanediol with phenazine solvate,
C₁₈H₂₄O₂Si.0.5(C₁₂H₈N₂), at 90 K has monoclinic
(P2₁/n) symmetry. It is of interest with respect to biological
activity. The structure displays O---H...O, O---H...N hydrogen bonding.
Contact distances are given.
;


_publ_section_title              
;
X-ray Crystallographic and NMR Studies of Silanediol Hydrogen-bonding Patterns
with Bifunctional Lewis Bases
;
#Added by publCIF



_audit_update_record             
;
2013-09-02 # Formatted by publCIF

;

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents


section
;
Introduction
;
;

;
section
;
Experimental
;
;
A suitable crystal was mounted on a glass fiber with silicone grease and placed
in the cold dinitrogen stream of a Bruker SMART APEXII CCD diffractometer with
Mo Ka radiation at 90((22)) K.
;
subsection
;
Synthesis and crystallization
;
;
Crystals were grown from slow evaporation of solution that contained 1:1 mixture
of dimesitylsilanediol and phenazine in benzene.
;
subsection
;
Refinement
;
;
Crystal data, data collection and structure refinement details are summarized in
Table 1. Structures were solved by direct methods and refined using all data.
All protons were located from a difference-Fourier map after all non-hydrogen
atoms were refined anisotropically several times. Positions and thermal
parameters were allowed to refine freely (xyzU).
;
section
;
Results and discussion
;
;

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            'dimesitylsilanediol with phenazine solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 O2 Si, 0.5(C12 H8 N2)'
_chemical_formula_sum            'C24 H28 N O2 Si'
_chemical_formula_weight         390.56

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7044(6)
_cell_length_b                   11.1778(6)
_cell_length_c                   16.8654(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.2130(10)
_cell_angle_gamma                90.00
_cell_volume                     2107.66(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23090
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4821
_reflns_number_gt                4515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0498P)²+0.7919P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4821
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.65959(2) 0.60386(2) 1.012073(17) 0.01382(9) Uani 1 1 d . . .
O1 O 0.52773(6) 0.64588(7) 0.95053(5) 0.01768(16) Uani 1 1 d . . .
H1 H 0.5026(15) 0.7148(17) 0.9597(10) 0.040(4) Uiso 1 1 d . . .
O2 O 0.64146(7) 0.53170(7) 1.09147(5) 0.01860(16) Uani 1 1 d . . .
H2 H 0.5947(16) 0.4744(17) 1.0800(11) 0.043(5) Uiso 1 1 d . . .
C1 C 0.74509(9) 0.74643(9) 1.04955(6) 0.01533(19) Uani 1 1 d . . .
C2 C 0.75457(9) 0.79878(9) 1.12795(6) 0.0171(2) Uani 1 1 d . . .
C3 C 0.79590(9) 0.91640(10) 1.14449(7) 0.0197(2) Uani 1 1 d . . .
H3 H 0.8005(13) 0.9517(14) 1.1980(9) 0.029(4) Uiso 1 1 d . . .
C4 C 0.83083(10) 0.98487(10) 1.08700(7) 0.0211(2) Uani 1 1 d . . .
C5 C 0.82757(9) 0.93167(10) 1.01178(7) 0.0203(2) Uani 1 1 d . . .
H5 H 0.8531(14) 0.9776(14) 0.9719(10) 0.032(4) Uiso 1 1 d . . .
C6 C 0.78540(9) 0.81525(9) 0.99225(6) 0.0170(2) Uani 1 1 d . . .
C7 C 0.78331(10) 0.76739(10) 0.90783(7) 0.0202(2) Uani 1 1 d . . .
H7A H 0.8357(14) 0.6977(15) 0.9112(10) 0.033(4) Uiso 1 1 d . . .
H7B H 0.7040(14) 0.7387(14) 0.8754(10) 0.029(4) Uiso 1 1 d . . .
H7C H 0.8060(14) 0.8308(15) 0.8763(10) 0.036(4) Uiso 1 1 d . . .
C8 C 0.86916(13) 1.11361(11) 1.10457(9) 0.0302(3) Uani 1 1 d . . .
H8A H 0.8102(19) 1.166(2) 1.0715(13) 0.064(6) Uiso 1 1 d . . .
H8B H 0.943(2) 1.129(2) 1.0920(14) 0.075(7) Uiso 1 1 d . . .
H8C H 0.8843(19) 1.1343(19) 1.1614(14) 0.064(6) Uiso 1 1 d . . .
C9 C 0.72183(11) 0.73424(11) 1.19713(7) 0.0237(2) Uani 1 1 d . . .
H9A H 0.6361(15) 0.7173(15) 1.1827(10) 0.036(4) Uiso 1 1 d . . .
H9B H 0.7629(14) 0.6575(15) 1.2096(9) 0.031(4) Uiso 1 1 d . . .
H9C H 0.7443(14) 0.7818(15) 1.2470(10) 0.036(4) Uiso 1 1 d . . .
C10 C 0.72968(9) 0.49730(9) 0.95328(6) 0.01428(19) Uani 1 1 d . . .
C11 C 0.68394(9) 0.46808(9) 0.86781(6) 0.01480(19) Uani 1 1 d . . .
C12 C 0.74452(9) 0.38557(9) 0.83260(6) 0.0167(2) Uani 1 1 d . . .
H12 H 0.7114(12) 0.3668(13) 0.7740(9) 0.021(3) Uiso 1 1 d . . .
C13 C 0.84795(9) 0.32756(9) 0.87856(7) 0.0181(2) Uani 1 1 d . . .
C14 C 0.89312(9) 0.35682(10) 0.96222(7) 0.0182(2) Uani 1 1 d . . .
H14 H 0.9661(13) 0.3177(13) 0.9951(9) 0.023(3) Uiso 1 1 d . . .
C15 C 0.83666(9) 0.43971(9) 0.99974(6) 0.0161(2) Uani 1 1 d . . .
C16 C 0.89390(10) 0.46316(10) 1.09141(6) 0.0202(2) Uani 1 1 d . . .
H16A H 0.9765(13) 0.4376(14) 1.1074(9) 0.027(4) Uiso 1 1 d . . .
H16B H 0.8950(13) 0.5460(15) 1.1066(9) 0.031(4) Uiso 1 1 d . . .
H16C H 0.8516(14) 0.4225(15) 1.1248(10) 0.034(4) Uiso 1 1 d . . .
C17 C 0.90771(11) 0.23468(11) 0.83977(8) 0.0247(2) Uani 1 1 d . . .
H17A H 0.892(2) 0.156(2) 0.8546(15) 0.082(7) Uiso 1 1 d . . .
H17B H 0.991(2) 0.247(2) 0.8539(14) 0.072(7) Uiso 1 1 d . . .
H17C H 0.872(2) 0.230(2) 0.7814(15) 0.071(6) Uiso 1 1 d . . .
C18 C 0.56845(9) 0.51715(10) 0.81037(6) 0.0177(2) Uani 1 1 d . . .
H18A H 0.5571(13) 0.6032(14) 0.8176(9) 0.027(4) Uiso 1 1 d . . .
H18B H 0.5005(13) 0.4770(14) 0.8210(9) 0.027(4) Uiso 1 1 d . . .
H18C H 0.5637(13) 0.5027(13) 0.7540(10) 0.027(4) Uiso 1 1 d . . .
C21 C 0.55757(11) 0.99403(11) 0.79995(7) 0.0239(2) Uani 1 1 d . . .
H21 H 0.5642(13) 0.9665(14) 0.7479(10) 0.029(4) Uiso 1 1 d . . .
C22 C 0.51410(10) 0.91872(10) 0.84744(7) 0.0207(2) Uani 1 1 d . . .
H22 H 0.4887(13) 0.8404(15) 0.8292(9) 0.028(4) Uiso 1 1 d . . .
C23 C 0.50615(9) 0.95759(9) 0.92625(7) 0.0173(2) Uani 1 1 d . . .
N23 N 0.46535(8) 0.88178(8) 0.97341(6) 0.01788(18) Uani 1 1 d . . .
C24 C 0.45791(9) 0.92259(9) 1.04669(7) 0.0177(2) Uani 1 1 d . . .
C25 C 0.41268(10) 0.84640(10) 1.09829(7) 0.0230(2) Uani 1 1 d . . .
H25 H 0.3874(14) 0.7660(14) 1.0793(9) 0.031(4) Uiso 1 1 d . . .
C26 C 0.40503(11) 0.88780(11) 1.17244(8) 0.0257(2) Uani 1 1 d . . .
H26 H 0.3730(15) 0.8358(16) 1.2065(10) 0.040(4) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Si1 O2 1.6300(8) . ?
Si1 O1 1.6528(8) . ?
Si1 C10 1.8858(10) . ?
Si1 C1 1.8885(10) . ?
O1 H1 0.855(19) . ?
O2 H2 0.828(19) . ?
C1 C2 1.4200(14) . ?
C1 C6 1.4206(14) . ?
C2 C3 1.4001(15) . ?
C2 C9 1.5143(15) . ?
C3 C4 1.3884(16) . ?
C3 H3 0.972(15) . ?
C4 C5 1.3913(16) . ?
C4 C8 1.5104(15) . ?
C5 C6 1.3962(15) . ?
C5 H5 0.962(16) . ?
C6 C7 1.5145(14) . ?
C7 H7A 0.983(17) . ?
C7 H7B 0.982(16) . ?
C7 H7C 0.969(17) . ?
C8 H8A 0.95(2) . ?
C8 H8B 0.97(2) . ?
C8 H8C 0.95(2) . ?
C9 H9A 0.979(17) . ?
C9 H9B 0.975(17) . ?
C9 H9C 0.964(17) . ?
C10 C11 1.4194(13) . ?
C10 C15 1.4198(14) . ?
C11 C12 1.3982(14) . ?
C11 C18 1.5138(14) . ?
C12 C13 1.3898(15) . ?
C12 H12 0.972(14) . ?
C13 C14 1.3913(15) . ?
C13 C17 1.5052(15) . ?
C14 C15 1.3940(14) . ?
C14 H14 0.974(15) . ?
C15 C16 1.5148(14) . ?
C16 H16A 0.967(15) . ?
C16 H16B 0.960(16) . ?
C16 H16C 0.966(17) . ?
C17 H17A 0.95(3) . ?
C17 H17B 0.94(2) . ?
C17 H17C 0.95(2) . ?
C18 H18A 0.983(15) . ?
C18 H18B 0.975(15) . ?
C18 H18C 0.949(15) . ?
C21 C22 1.3603(16) . ?
C21 C26 1.4257(17) 3_677 ?
C21 H21 0.955(15) . ?
C22 C23 1.4273(15) . ?
C22 H22 0.946(16) . ?
C23 N23 1.3429(14) . ?
C23 C24 1.4372(15) 3_677 ?
N23 C24 1.3442(14) . ?
C24 C25 1.4268(15) . ?
C24 C23 1.4372(15) 3_677 ?
C25 C26 1.3609(17) . ?
C25 H25 0.970(16) . ?
C26 C21 1.4257(17) 3_677 ?
C26 H26 0.968(18) . ?

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
O2 Si1 O1 109.40(4) . . ?
O2 Si1 C10 107.58(4) . . ?
O1 Si1 C10 108.66(4) . . ?
O2 Si1 C1 109.12(4) . . ?
O1 Si1 C1 105.91(4) . . ?
C10 Si1 C1 116.05(4) . . ?
Si1 O1 H1 116.7(12) . . ?
Si1 O2 H2 115.4(12) . . ?
C2 C1 C6 117.40(9) . . ?
C2 C1 Si1 123.17(8) . . ?
C6 C1 Si1 118.62(8) . . ?
C3 C2 C1 119.97(10) . . ?
C3 C2 C9 116.44(9) . . ?
C1 C2 C9 123.59(9) . . ?
C4 C3 C2 122.30(10) . . ?
C4 C3 H3 118.6(9) . . ?
C2 C3 H3 119.1(9) . . ?
C3 C4 C5 117.84(10) . . ?
C3 C4 C8 121.33(11) . . ?
C5 C4 C8 120.83(11) . . ?
C4 C5 C6 121.72(10) . . ?
C4 C5 H5 118.7(10) . . ?
C6 C5 H5 119.6(9) . . ?
C5 C6 C1 120.64(10) . . ?
C5 C6 C7 117.21(9) . . ?
C1 C6 C7 122.14(9) . . ?
C6 C7 H7A 112.9(9) . . ?
C6 C7 H7B 112.9(9) . . ?
H7A C7 H7B 104.1(13) . . ?
C6 C7 H7C 109.1(10) . . ?
H7A C7 H7C 110.1(13) . . ?
H7B C7 H7C 107.5(13) . . ?
C4 C8 H8A 110.5(13) . . ?
C4 C8 H8B 111.2(14) . . ?
H8A C8 H8B 107.7(18) . . ?
C4 C8 H8C 112.7(13) . . ?
H8A C8 H8C 109.1(18) . . ?
H8B C8 H8C 105.4(18) . . ?
C2 C9 H9A 112.1(10) . . ?
C2 C9 H9B 111.3(9) . . ?
H9A C9 H9B 106.7(13) . . ?
C2 C9 H9C 110.1(10) . . ?
H9A C9 H9C 108.6(13) . . ?
H9B C9 H9C 107.9(13) . . ?
C11 C10 C15 117.53(9) . . ?
C11 C10 Si1 125.97(8) . . ?
C15 C10 Si1 116.49(7) . . ?
C12 C11 C10 119.79(9) . . ?
C12 C11 C18 115.86(9) . . ?
C10 C11 C18 124.30(9) . . ?
C13 C12 C11 122.57(10) . . ?
C13 C12 H12 119.1(8) . . ?
C11 C12 H12 118.3(8) . . ?
C12 C13 C14 117.57(9) . . ?
C12 C13 C17 121.30(10) . . ?
C14 C13 C17 121.12(10) . . ?
C13 C14 C15 121.85(10) . . ?
C13 C14 H14 118.6(8) . . ?
C15 C14 H14 119.6(8) . . ?
C14 C15 C10 120.66(9) . . ?
C14 C15 C16 116.90(9) . . ?
C10 C15 C16 122.43(9) . . ?
C15 C16 H16A 109.7(9) . . ?
C15 C16 H16B 114.0(9) . . ?
H16A C16 H16B 106.1(13) . . ?
C15 C16 H16C 111.4(10) . . ?
H16A C16 H16C 110.0(13) . . ?
H16B C16 H16C 105.5(13) . . ?
C13 C17 H17A 112.0(15) . . ?
C13 C17 H17B 111.7(14) . . ?
H17A C17 H17B 110(2) . . ?
C13 C17 H17C 111.9(14) . . ?
H17A C17 H17C 99.3(19) . . ?
H17B C17 H17C 111.8(18) . . ?
C11 C18 H18A 113.8(9) . . ?
C11 C18 H18B 109.8(9) . . ?
H18A C18 H18B 106.3(12) . . ?
C11 C18 H18C 110.8(9) . . ?
H18A C18 H18C 108.6(12) . . ?
H18B C18 H18C 107.2(12) . . ?
C22 C21 C26 120.87(11) . 3_677 ?
C22 C21 H21 119.2(9) . . ?
C26 C21 H21 119.9(9) 3_677 . ?
C21 C22 C23 119.92(10) . . ?
C21 C22 H22 121.2(9) . . ?
C23 C22 H22 118.9(9) . . ?
N23 C23 C22 119.48(10) . . ?
N23 C23 C24 121.46(10) . 3_677 ?
C22 C23 C24 119.06(10) . 3_677 ?
C23 N23 C24 117.49(9) . . ?
N23 C24 C25 119.67(10) . . ?
N23 C24 C23 121.05(10) . 3_677 ?
C25 C24 C23 119.28(10) . 3_677 ?
C26 C25 C24 119.65(11) . . ?
C26 C25 H25 121.4(9) . . ?
C24 C25 H25 118.9(9) . . ?
C25 C26 C21 121.19(11) . 3_677 ?
C25 C26 H26 118.9(10) . . ?
C21 C26 H26 119.9(10) 3_677 . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Si1 C1 C2 -19.18(10) . . . . ?
O1 Si1 C1 C2 98.49(9) . . . . ?
C10 Si1 C1 C2 -140.87(8) . . . . ?
O2 Si1 C1 C6 171.42(7) . . . . ?
O1 Si1 C1 C6 -70.92(8) . . . . ?
C10 Si1 C1 C6 49.72(9) . . . . ?
C6 C1 C2 C3 3.60(14) . . . . ?
Si1 C1 C2 C3 -165.93(8) . . . . ?
C6 C1 C2 C9 -176.52(10) . . . . ?
Si1 C1 C2 C9 13.95(14) . . . . ?
C1 C2 C3 C4 -1.23(16) . . . . ?
C9 C2 C3 C4 178.89(10) . . . . ?
C2 C3 C4 C5 -2.11(16) . . . . ?
C2 C3 C4 C8 176.86(11) . . . . ?
C3 C4 C5 C6 3.00(16) . . . . ?
C8 C4 C5 C6 -175.97(11) . . . . ?
C4 C5 C6 C1 -0.57(16) . . . . ?
C4 C5 C6 C7 178.66(10) . . . . ?
C2 C1 C6 C5 -2.74(15) . . . . ?
Si1 C1 C6 C5 167.28(8) . . . . ?
C2 C1 C6 C7 178.07(9) . . . . ?
Si1 C1 C6 C7 -11.91(13) . . . . ?
O2 Si1 C10 C11 124.89(9) . . . . ?
O1 Si1 C10 C11 6.55(10) . . . . ?
C1 Si1 C10 C11 -112.60(9) . . . . ?
O2 Si1 C10 C15 -53.75(8) . . . . ?
O1 Si1 C10 C15 -172.08(7) . . . . ?
C1 Si1 C10 C15 68.76(9) . . . . ?
C15 C10 C11 C12 -0.23(14) . . . . ?
Si1 C10 C11 C12 -178.86(7) . . . . ?
C15 C10 C11 C18 177.29(9) . . . . ?
Si1 C10 C11 C18 -1.34(14) . . . . ?
C10 C11 C12 C13 1.54(15) . . . . ?
C18 C11 C12 C13 -176.19(9) . . . . ?
C11 C12 C13 C14 -1.90(16) . . . . ?
C11 C12 C13 C17 176.94(10) . . . . ?
C12 C13 C14 C15 1.00(16) . . . . ?
C17 C13 C14 C15 -177.84(10) . . . . ?
C13 C14 C15 C10 0.23(16) . . . . ?
C13 C14 C15 C16 179.45(10) . . . . ?
C11 C10 C15 C14 -0.62(14) . . . . ?
Si1 C10 C15 C14 178.14(8) . . . . ?
C11 C10 C15 C16 -179.80(9) . . . . ?
Si1 C10 C15 C16 -1.04(13) . . . . ?
C26 C21 C22 C23 -0.35(17) 3_677 . . . ?
C21 C22 C23 N23 -178.68(10) . . . . ?
C21 C22 C23 C24 1.35(15) . . . 3_677 ?
C22 C23 N23 C24 -179.17(9) . . . . ?
C24 C23 N23 C24 0.80(16) 3_677 . . . ?
C23 N23 C24 C25 178.65(9) . . . . ?
C23 N23 C24 C23 -0.80(16) . . . 3_677 ?
N23 C24 C25 C26 -179.93(10) . . . . ?
C23 C24 C25 C26 -0.47(16) 3_677 . . . ?
C24 C25 C26 C21 -0.55(18) . . . 3_677 ?

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 0.828(19) 1.920(19) 2.7446(11) 173.7(18) 3_667
O1 H1 N23 0.855(19) 1.946(19) 2.7932(12) 170.8(16) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.043

_database_code_depnum_ccdc_archive 'CCDC 958790'
data_a3


_publ_section_references         
;
(1)A short history of SHELX, George M. Sheldrick, Acta Cryst. (2008).
A64, 112-122 References:

(2) Bruker (2002). SMART (Version 5.054) Bruker (2004) SMART APEX
(Version 1.2.1.21) and SAINT (Version 7.23a). Bruker AXS Inc., Madison,
Wisconsin, USA.

(3) An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

(4) Sheldrick, G.M., SADABS (2003). Version 2.10, 'Siemens Area Detector
Absorption Correction' Universitat Gottingen: Gottingen, Germany.

(5) Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

(6) Sheldrick, G. M., (1997). SHELXS97 and SHELXL97. Universitat
Gottingen: Gottingen, Germany.

(7) On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

(8) Sheldrick, G. M., (2008). SHELXS97 and SHELXL97. Acta Cryst.
A64, 112-122. 8.

(9) Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann,
H., OLEX2: A complete structure solution, refinement and analysis
program (2009). J. Appl. Cryst., 42, 339-341.

(10) Hooft, R.W.W, Straver, L.H. & Spek,A.L. (2008). J. Appl, Cryst. 41,
96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron
;
#Added by publCIF




_publ_section_acknowledgements   
;
The authors gratefully acknowledge UC Davis, 3M Corporation, National Science
Foundation (CHE-0847358), UC Davis Bradford Borge Fellowship,Achievement
Rewards for College Scientists Scholarship(ARCS),and the U.S. Department of
Education Graduate Assistance in Areas of National Need (GAANN) Fellowship. We
thank the National Science Foundation (#0840444) for the Bruker AXS Dual
source diffractometer.
;
#Added by publCIF




_publ_section_keywords           
;
Cooperative hydrogen bonding, silanediol, self-association
;

#Added by publCIF



_publ_section_related_literature ?

_publ_contact_author_name        'Annaliese K. Franz'

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;


_publ_requested_category         ?

_publ_requested_journal          ?

_publ_contact_author_fax         530-752-8995

_publ_contact_author_phone       530-752-9820

_publ_contact_author_email       akfranz@ucdavis.edu

_publ_contact_author_address     
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616


;


# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Tran, Ngon T.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Wilson, Sean O.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Franz, Annaliese K.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. ?




_publ_section_abstract           
;
The structure of dimesitylsilanediol with 1,4-dimethoxybenzene solvate,
C₁₈H₂₄O₂Si.0.5(C₈H₁₀O₂), at 90 K has triclinic (P\=1)
symmetry. It is of interest with respect to catalysis. The structure displays
O---H...O hydrogen bonding. Contact distances are given.
;


_publ_section_title              
;
X-ray Crystallographic and NMR Studies of Silanediol Hydrogen-bonding Patterns
with Bifunctional Lewis Bases
;
#Added by publCIF



_audit_update_record             
;
2013-09-02 # Formatted by publCIF

;

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents


section
;
Introduction
;
;

;
section
;
Experimental
;
;
A suitable crystal was mounted on a glass fiber with silicone grease and placed
in the cold dinitrogen stream of a Bruker SMART APEXII CCD diffractometer with
Mo Ka radiation at 90((22)) K.
;
subsection
;
Synthesis and crystallization
;
;
Crystals were grown from slow evaporation of solution that contained 1:1
mixture of dimesitylsilanediol and 1,4-dimethoxybenzene in benzene.
;
subsection
;
Refinement
;
;
Crystal data, data collection and structure refinement details are summarized
in Table 1. Structures were solved by direct methods and refined using all
data. All protons were located from a difference-Fourier map after all
non-hydrogen atoms were refined anisotropically several times. Positions and
thermal parameters were allowed to refine freely (xyzU).
;
section
;
Results and discussion
;
;

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            
'dimesitylsilanediol with 1,4-dimethoxybenzene solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H24 O2 Si, 0.5(C8 H10 O2)'
_chemical_formula_sum            'C22 H29 O3 Si'
_chemical_formula_weight         369.54

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4092(2)
_cell_length_b                   9.0220(2)
_cell_length_c                   13.4486(3)
_cell_angle_alpha                99.15
_cell_angle_beta                 97.10
_cell_angle_gamma                93.79
_cell_volume                     995.76(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    8679
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      33.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             398
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9504
_exptl_absorpt_correction_T_max  0.9530
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15470
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         33.27
_reflns_number_total             7069
_reflns_number_gt                6024
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.1714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7069
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Si1 Si 0.06201(3) 0.56367(3) 0.172557(17) 0.01402(6) Uani 1 1 d . . .
O1 O 0.18426(8) 0.63664(7) 0.10226(5) 0.01762(12) Uani 1 1 d . . .
H1 H 0.1918(19) 0.7325(19) 0.1053(12) 0.041(4) Uiso 1 1 d . . .
O2 O -0.03987(8) 0.41625(7) 0.10139(5) 0.01773(12) Uani 1 1 d . . .
H2 H -0.089(2) 0.419(2) 0.0406(14) 0.051(5) Uiso 1 1 d . . .
C1 C -0.06064(10) 0.72134(9) 0.21920(6) 0.01625(15) Uani 1 1 d . . .
C2 C 0.00435(11) 0.83178(10) 0.30428(7) 0.02036(17) Uani 1 1 d . . .
C3 C -0.08816(12) 0.94610(10) 0.34151(7) 0.02254(18) Uani 1 1 d . . .
H3 H -0.0403(17) 1.0216(16) 0.4012(11) 0.029(3) Uiso 1 1 d . . .
C4 C -0.24388(12) 0.95644(10) 0.29662(7) 0.02098(17) Uani 1 1 d . . .
C5 C -0.30446(11) 0.85294(10) 0.20977(7) 0.01899(16) Uani 1 1 d . . .
H5 H -0.4122(16) 0.8631(15) 0.1793(10) 0.024(3) Uiso 1 1 d . . .
C6 C -0.21659(10) 0.73675(9) 0.17066(6) 0.01614(15) Uani 1 1 d . . .
C7 C -0.29393(11) 0.63243(11) 0.07535(7) 0.01988(16) Uani 1 1 d . . .
H7A H -0.3992(18) 0.6654(16) 0.0534(11) 0.033(4) Uiso 1 1 d . . .
H7B H -0.3133(16) 0.5289(16) 0.0869(10) 0.027(3) Uiso 1 1 d . . .
H7C H -0.2312(16) 0.6357(15) 0.0219(10) 0.026(3) Uiso 1 1 d . . .
C8 C -0.34752(15) 1.07387(12) 0.33959(9) 0.0287(2) Uani 1 1 d . . .
H8A H -0.448(2) 1.029(2) 0.3554(14) 0.054(5) Uiso 1 1 d . . .
H8B H -0.367(2) 1.1416(19) 0.2944(13) 0.046(4) Uiso 1 1 d . . .
H8C H -0.293(2) 1.1366(19) 0.4013(13) 0.044(4) Uiso 1 1 d . . .
C9 C 0.17411(13) 0.83187(13) 0.35732(9) 0.0310(2) Uani 1 1 d . . .
H9A H 0.208(2) 0.9307(19) 0.3995(12) 0.043(4) Uiso 1 1 d . . .
H9B H 0.2517(19) 0.8121(17) 0.3103(12) 0.035(4) Uiso 1 1 d . . .
H9C H 0.182(2) 0.753(2) 0.3998(14) 0.051(5) Uiso 1 1 d . . .
C10 C 0.16597(10) 0.47589(9) 0.27780(6) 0.01538(14) Uani 1 1 d . . .
C11 C 0.33246(10) 0.45866(9) 0.29244(6) 0.01594(15) Uani 1 1 d . . .
C12 C 0.39791(11) 0.38838(10) 0.37179(7) 0.01799(16) Uani 1 1 d . . .
H12 H 0.5163(17) 0.3803(15) 0.3810(10) 0.026(3) Uiso 1 1 d . . .
C13 C 0.30371(11) 0.33284(10) 0.43784(7) 0.01944(16) Uani 1 1 d . . .
C14 C 0.13952(12) 0.34781(11) 0.42268(7) 0.02152(17) Uani 1 1 d . . .
H14 H 0.0714(16) 0.3095(15) 0.4683(10) 0.025(3) Uiso 1 1 d . . .
C15 C 0.06939(11) 0.41702(10) 0.34419(7) 0.01913(16) Uani 1 1 d . . .
C16 C -0.11089(12) 0.42342(15) 0.33194(9) 0.0291(2) Uani 1 1 d . . .
H16A H -0.1563(18) 0.3922(17) 0.3909(12) 0.035(4) Uiso 1 1 d . . .
H16B H -0.163(2) 0.360(2) 0.2710(14) 0.051(5) Uiso 1 1 d . . .
H16C H -0.139(2) 0.523(2) 0.3284(13) 0.050(5) Uiso 1 1 d . . .
C17 C 0.37743(14) 0.25671(12) 0.52240(8) 0.0259(2) Uani 1 1 d . . .
H17A H 0.489(2) 0.290(2) 0.5439(14) 0.054(5) Uiso 1 1 d . . .
H17B H 0.327(2) 0.281(2) 0.5827(14) 0.055(5) Uiso 1 1 d . . .
H17C H 0.3690(19) 0.1501(19) 0.5020(12) 0.042(4) Uiso 1 1 d . . .
C18 C 0.44686(11) 0.51363(12) 0.22543(7) 0.02185(17) Uani 1 1 d . . .
H18A H 0.5526(19) 0.4828(17) 0.2425(11) 0.034(4) Uiso 1 1 d . . .
H18B H 0.4554(18) 0.6205(17) 0.2330(11) 0.033(4) Uiso 1 1 d . . .
H18C H 0.4138(17) 0.4761(16) 0.1522(11) 0.030(3) Uiso 1 1 d . . .
O21 O 0.21153(9) 0.94177(8) 0.07318(6) 0.02667(15) Uani 1 1 d . . .
C21 C 0.35465(12) 0.97674(10) 0.03800(7) 0.02155(17) Uani 1 1 d . . .
C22 C 0.39845(12) 0.87095(10) -0.03892(7) 0.02260(18) Uani 1 1 d . . .
H22 H 0.3261(17) 0.7813(16) -0.0660(10) 0.027(3) Uiso 1 1 d . . .
C23 C 0.54325(13) 0.89306(10) -0.07654(7) 0.02253(17) Uani 1 1 d . . .
H23 H 0.5682(18) 0.8186(17) -0.1314(11) 0.032(4) Uiso 1 1 d . . .
C24 C 0.13972(16) 1.06276(13) 0.12926(10) 0.0329(2) Uani 1 1 d . . .
H24A H 0.0356(19) 1.0251(17) 0.1411(11) 0.036(4) Uiso 1 1 d . . .
H24B H 0.1309(19) 1.1443(18) 0.0892(12) 0.042(4) Uiso 1 1 d . . .
H24C H 0.2069(19) 1.0952(17) 0.1968(12) 0.038(4) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
Si1 O2 1.6311(7) . ?
Si1 O1 1.6531(7) . ?
Si1 C10 1.8808(9) . ?
Si1 C1 1.8844(9) . ?
O1 H1 0.857(17) . ?
O2 H2 0.874(18) . ?
C1 C6 1.4166(12) . ?
C1 C2 1.4182(12) . ?
C2 C3 1.3992(13) . ?
C2 C9 1.5148(14) . ?
C3 C4 1.3880(14) . ?
C3 H3 0.991(14) . ?
C4 C5 1.3924(13) . ?
C4 C8 1.5059(13) . ?
C5 C6 1.3945(12) . ?
C5 H5 0.964(14) . ?
C6 C7 1.5103(12) . ?
C7 H7A 0.978(15) . ?
C7 H7B 0.977(14) . ?
C7 H7C 0.946(14) . ?
C8 H8A 0.971(19) . ?
C8 H8B 0.937(18) . ?
C8 H8C 0.969(17) . ?
C9 H9A 0.981(17) . ?
C9 H9B 0.969(16) . ?
C9 H9C 0.983(19) . ?
C10 C11 1.4119(12) . ?
C10 C15 1.4184(12) . ?
C11 C12 1.4000(12) . ?
C11 C18 1.5090(12) . ?
C12 C13 1.3895(13) . ?
C12 H12 0.997(14) . ?
C13 C14 1.3893(14) . ?
C13 C17 1.5100(13) . ?
C14 C15 1.3988(13) . ?
C14 H14 0.975(14) . ?
C15 C16 1.5106(13) . ?
C16 H16A 0.993(15) . ?
C16 H16B 0.959(18) . ?
C16 H16C 0.950(18) . ?
C17 H17A 0.961(19) . ?
C17 H17B 0.964(18) . ?
C17 H17C 0.952(17) . ?
C18 H18A 0.961(15) . ?
C18 H18B 0.950(15) . ?
C18 H18C 0.988(14) . ?
O21 C21 1.3820(12) . ?
O21 C24 1.4363(13) . ?
C21 C22 1.3940(14) . ?
C21 C23 1.3959(13) 2_675 ?
C22 C23 1.3895(15) . ?
C22 H22 0.971(14) . ?
C23 C21 1.3959(13) 2_675 ?
C23 H23 0.969(14) . ?
C24 H24A 0.959(16) . ?
C24 H24B 0.980(17) . ?
C24 H24C 0.998(16) . ?

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
O2 Si1 O1 107.30(3) . . ?
O2 Si1 C10 101.01(4) . . ?
O1 Si1 C10 114.52(4) . . ?
O2 Si1 C1 115.54(4) . . ?
O1 Si1 C1 105.27(4) . . ?
C10 Si1 C1 113.36(4) . . ?
Si1 O1 H1 117.8(11) . . ?
Si1 O2 H2 122.3(12) . . ?
C6 C1 C2 117.77(8) . . ?
C6 C1 Si1 122.29(6) . . ?
C2 C1 Si1 119.92(6) . . ?
C3 C2 C1 120.21(8) . . ?
C3 C2 C9 117.75(8) . . ?
C1 C2 C9 122.04(8) . . ?
C4 C3 C2 121.73(8) . . ?
C4 C3 H3 119.6(8) . . ?
C2 C3 H3 118.7(8) . . ?
C3 C4 C5 118.03(8) . . ?
C3 C4 C8 122.08(9) . . ?
C5 C4 C8 119.89(9) . . ?
C4 C5 C6 121.95(8) . . ?
C4 C5 H5 116.6(8) . . ?
C6 C5 H5 121.4(8) . . ?
C5 C6 C1 120.15(8) . . ?
C5 C6 C7 117.22(8) . . ?
C1 C6 C7 122.63(7) . . ?
C6 C7 H7A 109.1(8) . . ?
C6 C7 H7B 112.1(8) . . ?
H7A C7 H7B 106.5(12) . . ?
C6 C7 H7C 110.9(8) . . ?
H7A C7 H7C 107.5(12) . . ?
H7B C7 H7C 110.5(11) . . ?
C4 C8 H8A 112.2(11) . . ?
C4 C8 H8B 110.0(10) . . ?
H8A C8 H8B 110.8(15) . . ?
C4 C8 H8C 112.1(10) . . ?
H8A C8 H8C 107.4(14) . . ?
H8B C8 H8C 104.1(14) . . ?
C2 C9 H9A 109.5(10) . . ?
C2 C9 H9B 112.9(9) . . ?
H9A C9 H9B 107.6(13) . . ?
C2 C9 H9C 111.3(11) . . ?
H9A C9 H9C 109.8(14) . . ?
H9B C9 H9C 105.6(13) . . ?
C11 C10 C15 117.79(8) . . ?
C11 C10 Si1 124.44(6) . . ?
C15 C10 Si1 117.70(6) . . ?
C12 C11 C10 120.12(8) . . ?
C12 C11 C18 117.18(8) . . ?
C10 C11 C18 122.70(8) . . ?
C13 C12 C11 122.09(8) . . ?
C13 C12 H12 119.9(8) . . ?
C11 C12 H12 118.0(8) . . ?
C14 C13 C12 117.87(8) . . ?
C14 C13 C17 121.18(9) . . ?
C12 C13 C17 120.95(9) . . ?
C13 C14 C15 121.80(8) . . ?
C13 C14 H14 119.1(8) . . ?
C15 C14 H14 119.1(8) . . ?
C14 C15 C10 120.30(8) . . ?
C14 C15 C16 117.79(8) . . ?
C10 C15 C16 121.89(8) . . ?
C15 C16 H16A 110.8(9) . . ?
C15 C16 H16B 112.0(11) . . ?
H16A C16 H16B 108.6(13) . . ?
C15 C16 H16C 111.1(11) . . ?
H16A C16 H16C 107.1(13) . . ?
H16B C16 H16C 107.1(15) . . ?
C13 C17 H17A 112.4(11) . . ?
C13 C17 H17B 111.1(11) . . ?
H17A C17 H17B 104.5(15) . . ?
C13 C17 H17C 111.0(10) . . ?
H17A C17 H17C 108.2(14) . . ?
H17B C17 H17C 109.4(15) . . ?
C11 C18 H18A 110.7(9) . . ?
C11 C18 H18B 111.2(9) . . ?
H18A C18 H18B 107.9(12) . . ?
C11 C18 H18C 113.7(8) . . ?
H18A C18 H18C 107.2(12) . . ?
H18B C18 H18C 105.9(12) . . ?
C21 O21 C24 117.51(8) . . ?
O21 C21 C22 116.36(8) . . ?
O21 C21 C23 124.14(9) . 2_675 ?
C22 C21 C23 119.47(9) . 2_675 ?
C23 C22 C21 120.68(9) . . ?
C23 C22 H22 120.3(8) . . ?
C21 C22 H22 119.0(8) . . ?
C22 C23 C21 119.85(9) . 2_675 ?
C22 C23 H23 118.4(9) . . ?
C21 C23 H23 121.7(9) 2_675 . ?
O21 C24 H24A 108.4(9) . . ?
O21 C24 H24B 108.5(9) . . ?
H24A C24 H24B 110.9(13) . . ?
O21 C24 H24C 108.6(9) . . ?
H24A C24 H24C 107.7(13) . . ?
H24B C24 H24C 112.7(13) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Si1 C1 C6 -20.86(9) . . . . ?
O1 Si1 C1 C6 97.31(7) . . . . ?
C10 Si1 C1 C6 -136.78(7) . . . . ?
O2 Si1 C1 C2 160.66(7) . . . . ?
O1 Si1 C1 C2 -81.17(8) . . . . ?
C10 Si1 C1 C2 44.74(8) . . . . ?
C6 C1 C2 C3 3.71(14) . . . . ?
Si1 C1 C2 C3 -177.75(7) . . . . ?
C6 C1 C2 C9 -175.83(9) . . . . ?
Si1 C1 C2 C9 2.72(13) . . . . ?
C1 C2 C3 C4 -0.68(15) . . . . ?
C9 C2 C3 C4 178.87(10) . . . . ?
C2 C3 C4 C5 -2.78(14) . . . . ?
C2 C3 C4 C8 176.56(9) . . . . ?
C3 C4 C5 C6 3.21(14) . . . . ?
C8 C4 C5 C6 -176.15(9) . . . . ?
C4 C5 C6 C1 -0.15(14) . . . . ?
C4 C5 C6 C7 -179.30(8) . . . . ?
C2 C1 C6 C5 -3.30(13) . . . . ?
Si1 C1 C6 C5 178.19(7) . . . . ?
C2 C1 C6 C7 175.81(8) . . . . ?
Si1 C1 C6 C7 -2.70(12) . . . . ?
O2 Si1 C10 C11 109.21(7) . . . . ?
O1 Si1 C10 C11 -5.74(8) . . . . ?
C1 Si1 C10 C11 -126.56(7) . . . . ?
O2 Si1 C10 C15 -67.85(7) . . . . ?
O1 Si1 C10 C15 177.20(6) . . . . ?
C1 Si1 C10 C15 56.38(8) . . . . ?
C15 C10 C11 C12 -1.39(12) . . . . ?
Si1 C10 C11 C12 -178.44(6) . . . . ?
C15 C10 C11 C18 178.71(8) . . . . ?
Si1 C10 C11 C18 1.66(12) . . . . ?
C10 C11 C12 C13 0.40(13) . . . . ?
C18 C11 C12 C13 -179.70(8) . . . . ?
C11 C12 C13 C14 0.49(13) . . . . ?
C11 C12 C13 C17 179.64(8) . . . . ?
C12 C13 C14 C15 -0.35(14) . . . . ?
C17 C13 C14 C15 -179.50(9) . . . . ?
C13 C14 C15 C10 -0.67(14) . . . . ?
C13 C14 C15 C16 178.10(9) . . . . ?
C11 C10 C15 C14 1.52(13) . . . . ?
Si1 C10 C15 C14 178.78(7) . . . . ?
C11 C10 C15 C16 -177.20(9) . . . . ?
Si1 C10 C15 C16 0.06(12) . . . . ?
C24 O21 C21 C22 -162.31(9) . . . . ?
C24 O21 C21 C23 19.55(14) . . . 2_675 ?
O21 C21 C22 C23 -177.46(8) . . . . ?
C23 C21 C22 C23 0.77(16) 2_675 . . . ?
C21 C22 C23 C21 -0.77(16) . . . 2_675 ?

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 0.874(18) 1.961(18) 2.8087(9) 163.1(17) 2_565
O1 H1 O21 0.857(17) 2.004(17) 2.8399(9) 164.9(15) .

_diffrn_measured_fraction_theta_max 0.954
_diffrn_reflns_theta_full        33.27
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.052

_database_code_depnum_ccdc_archive 'CCDC 958824'
data_a3


_publ_section_figure_captions    
;

;
#Added by publCIF




_publ_section_references         
;
(1)A short history of SHELX, George M. Sheldrick, Acta Cryst. (2008).
A64, 112-122 References:

(2) Bruker (2002). SMART (Version 5.054) Bruker (2004) SMART APEX
(Version 1.2.1.21) and SAINT (Version 7.23a). Bruker AXS Inc., Madison,
Wisconsin, USA.

(3) An Empirical Correction for Absorption Anisotropy, Blessing, R. H. (1995).
Acta Cryst., A51, 33-38.

(4) Sheldrick, G.M., SADABS (2003). Version 2.10, 'Siemens Area Detector
Absorption Correction' Universitat Gottingen: Gottingen, Germany.

(5) Sheldrick, G.M., (2002). SHELXTL. Version 6.1. Bruker AXS Inc.,
Madison, Wisconsin, USA.

(6) Sheldrick, G. M., (1997). SHELXS97 and SHELXL97. Universitat
Gottingen: Gottingen, Germany.

(7) On Enantiomorph-Polarity Estimation, Flack, H.D. (1983). Acta Cryst., A39,
876-881.

(8) Sheldrick, G. M., (2008). SHELXS97 and SHELXL97. Acta Cryst.
A64, 112-122. 8.

(9) Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann,
H., OLEX2: A complete structure solution, refinement and analysis
program (2009). J. Appl. Cryst., 42, 339-341.

(10) Hooft, R.W.W, Straver, L.H. & Spek,A.L. (2008). J. Appl, Cryst. 41,
96-103. Thompson,A.L. & Watkin, D.J. (2009). Tetrahedron
;
#Added by publCIF




_publ_section_acknowledgements   
;
The authors gratefully acknowledge UC Davis, 3M Corporation, National Science
Foundation (CHE-0847358), UC Davis Bradford Borge Fellowship,Achievement
Rewards for College Scientists Scholarship(ARCS),and the U.S. Department of
Education Graduate Assistance in Areas of National Need (GAANN) Fellowship. We
thank the National Science Foundation (#0840444) for the Bruker AXS Dual
source diffractometer.
;
#Added by publCIF




_publ_section_synopsis           .
#Added by publCIF




_publ_section_keywords           
;
Cooperative hydrogen bonding, silanediol, self-association
;

#Added by publCIF



_publ_section_related_literature ?

_publ_contact_author_name        'Annaliese K. Franz'

_publ_contact_letter             
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;


_publ_requested_category         ?

_publ_requested_journal          ?

_publ_contact_author_fax         530-752-8995

_publ_contact_author_phone       530-752-9820

_publ_contact_author_email       akfranz@ucdavis.edu

_publ_contact_author_address     
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616


;


# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Tran, Ngon T.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Wilson, Sean O.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. .
'Franz, Annaliese K.'
;
Department of Chemistry
University of California, Davis
One Shields Ave
Davis, CA 95616
;
. ?




_publ_section_abstract           
;
The structure of dimesitylsilanediol with 4,4'-dipyridyl solvate,
C₁₈H₂₄O₂Si.0.5(C₁₀H₈N₂).CH₂Cl₂, at 90 K has triclinic
(P\=1) symmetry. It is of interest with respect to catalysis. The
structure displays O---H...O, O---H...N hydrogen bonding. Contact distances
are given.
;


_publ_section_title              
;
X-ray Crystallographic and NMR Studies of Silanediol Hydrogen-bonding Patterns
with Bifunctional Lewis Bases
;
#Added by publCIF


_publcif_datablock.id            {ac0efd36-45ce-42c9-ad3d-db89b4f4b36c}
_audit_update_record             
;
2013-09-01 # Formatted by publCIF

;

# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents


section
;
Introduction
;
;

;
section
;
Experimental
;
;
A suitable crystal was mounted on a glass fiber with silicone grease and placed
in the cold dinitrogen stream of a Bruker SMART diffractometer with Mo
Ka radiation at 90((22)) K.
;
subsection
;
Synthesis and crystallization
;
;
Crystals were grown from slow evaporation of solution that contained 1:1
mixture of dimesitylsilanediol and 4,4'-dipyridyl in benzene.
;
subsection
;
Refinement
;
;
Crystal data, data collection and structure refinement details are summarized
in Table 1. Structures were solved by direct methods and refined using all
data. All protons were located from a difference-Fourier map after all
non-hydrogen atoms were refined anisotropically several times. Positions and
thermal parameters were allowed to refine freely (xyzU).
;
section
;
Results and discussion
;
;

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            
"dimesitylsilanediol with 4,4'-dipyridyl solvate"
_chemical_melting_point          ?
_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

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4628(15)
_cell_length_b                   12.198(3)
_cell_length_c                   12.589(2)
_cell_angle_alpha                99.002(18)
_cell_angle_beta                 98.19(2)
_cell_angle_gamma                108.44(2)
_cell_volume                     1191.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    7694
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.6

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             490
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_T_max  0.8832
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2006)'

_exptl_special_details           ?

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8841
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.57
_reflns_number_total             5204
_reflns_number_gt                4543
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.6524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5204
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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
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_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
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

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) .

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.948
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.051
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{ac0efd36-45ce-42c9-ad3d-db89b4f4b36c} y y y

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{ac0efd36-45ce-42c9-ad3d-db89b4f4b36c} '_publcif_info_datablock.publ_exptl'
{ac0efd36-45ce-42c9-ad3d-db89b4f4b36c} '_geom_hbond_atom_site_label_D'

_database_code_depnum_ccdc_archive 'CCDC 958825'
