# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1481646'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H16 O Si, C6 H8 N, Cl'
_chemical_formula_sum            'C24 H24 Cl N O Si'
_chemical_formula_weight         405.98

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

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

_cell_length_a                   8.8980(18)
_cell_length_b                   9.2470(18)
_cell_length_c                   14.663(3)
_cell_angle_alpha                93.17(3)
_cell_angle_beta                 98.79(3)
_cell_angle_gamma                114.16(3)
_cell_volume                     1078.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3609
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'NONIUS KAPPA CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32962
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4905
_reflns_number_gt                3609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XSEED
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0774P)²+0.8566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4905
_refine_ls_number_parameters     246
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1640
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.32768(8) 0.22467(8) 0.23502(4) 0.03043(18) Uani 1 1 d . . .
Cl1 Cl 0.27584(9) 0.27604(9) 0.51152(5) 0.03473(19) Uani 0.82 1 d P A 1
O1 O 0.4246(2) 0.2329(2) 0.34029(12) 0.0412(4) Uani 1 1 d . . .
C14 C 0.1233(3) 0.0431(3) 0.20611(16) 0.0303(5) Uani 1 1 d . . .
C8 C 0.4718(3) 0.2176(3) 0.15652(17) 0.0317(5) Uani 1 1 d . . .
C2 C 0.2891(3) 0.4067(3) 0.22002(16) 0.0316(5) Uani 1 1 d . . .
C18 C -0.0941(3) -0.1766(3) 0.09634(19) 0.0410(6) Uani 1 1 d . . .
H18 H -0.1357 -0.2321 0.0349 0.049 Uiso 1 1 calc R . .
C15 C 0.0284(3) -0.0145(3) 0.27504(18) 0.0357(5) Uani 1 1 d . . .
H15 H 0.0694 0.0399 0.3367 0.043 Uiso 1 1 calc R . .
C19 C 0.0581(3) -0.0413(3) 0.11648(17) 0.0343(5) Uani 1 1 d . . .
H19 H 0.1191 -0.0055 0.0682 0.041 Uiso 1 1 calc R . .
C13 C 0.4976(3) 0.3053(3) 0.08151(18) 0.0386(6) Uani 1 1 d . . .
H13 H 0.4397 0.3707 0.0695 0.046 Uiso 1 1 calc R . .
C9 C 0.5607(3) 0.1236(3) 0.1719(2) 0.0402(6) Uani 1 1 d . . .
H9 H 0.5466 0.0630 0.2228 0.048 Uiso 1 1 calc R . .
C3 C 0.1415(3) 0.4016(3) 0.16746(19) 0.0400(6) Uani 1 1 d . . .
H3 H 0.0542 0.3014 0.1394 0.048 Uiso 1 1 calc R . .
C7 C 0.4143(3) 0.5571(3) 0.25913(19) 0.0412(6) Uani 1 1 d . . .
H7 H 0.5163 0.5643 0.2947 0.049 Uiso 1 1 calc R . .
C10 C 0.6689(3) 0.1169(3) 0.1144(2) 0.0476(7) Uani 1 1 d . . .
H10 H 0.7275 0.0519 0.1259 0.057 Uiso 1 1 calc R . .
C17 C -0.1849(3) -0.2301(3) 0.1658(2) 0.0446(6) Uani 1 1 d . . .
H17 H -0.2888 -0.3225 0.1521 0.054 Uiso 1 1 calc R . .
C4 C 0.1202(4) 0.5409(4) 0.1556(2) 0.0471(7) Uani 1 1 d . . .
H4 H 0.0189 0.5350 0.1198 0.057 Uiso 1 1 calc R . .
C12 C 0.6059(3) 0.2992(4) 0.0238(2) 0.0468(7) Uani 1 1 d . . .
H12 H 0.6212 0.3598 -0.0270 0.056 Uiso 1 1 calc R . .
C11 C 0.6910(3) 0.2049(4) 0.0407(2) 0.0475(7) Uani 1 1 d . . .
H11 H 0.7651 0.2006 0.0014 0.057 Uiso 1 1 calc R . .
C16 C -0.1242(3) -0.1492(3) 0.2552(2) 0.0437(6) Uani 1 1 d . . .
H16 H -0.1866 -0.1855 0.3030 0.052 Uiso 1 1 calc R . .
C6 C 0.3938(4) 0.6957(3) 0.2474(2) 0.0494(7) Uani 1 1 d . . .
H6 H 0.4810 0.7964 0.2748 0.059 Uiso 1 1 calc R . .
C5 C 0.2464(4) 0.6877(4) 0.1958(2) 0.0488(7) Uani 1 1 d . . .
H5 H 0.2317 0.7827 0.1879 0.059 Uiso 1 1 calc R . .
H1 H 0.3743 0.2499 0.3919 0.080(12) Uiso 1 1 d R . .
N20 N 0.2505(4) 0.6002(4) 0.5293(2) 0.0359(6) Uiso 0.82 1 d P B 1
H20 H 0.2649 0.5115 0.5272 0.043 Uiso 0.82 1 calc PR B 1
C21 C 0.1724(4) 0.6287(4) 0.5951(2) 0.0389(7) Uiso 0.82 1 d P B 1
C22 C 0.1471(5) 0.7657(6) 0.5956(3) 0.0494(9) Uiso 0.82 1 d P B 1
H22 H 0.0910 0.7891 0.6405 0.059 Uiso 0.82 1 calc PR B 1
C25 C 0.3070(5) 0.6985(5) 0.4677(3) 0.0519(9) Uiso 0.82 1 d P B 1
H25 H 0.3632 0.6741 0.4232 0.062 Uiso 0.82 1 calc PR B 1
C26 C 0.1225(5) 0.5101(5) 0.6637(3) 0.0548(9) Uiso 0.82 1 d P B 1
H26A H 0.0845 0.4017 0.6318 0.082 Uiso 0.82 1 calc PR B 1
H26B H 0.0313 0.5182 0.6904 0.082 Uiso 0.82 1 calc PR B 1
H26C H 0.2193 0.5333 0.7135 0.082 Uiso 0.82 1 calc PR B 1
C24 C 0.2832(6) 0.8364(6) 0.4690(4) 0.0615(11) Uiso 0.82 1 d P B 1
H24 H 0.3241 0.9084 0.4255 0.074 Uiso 0.82 1 calc PR B 1
C23 C 0.2025(6) 0.8696(6) 0.5315(3) 0.0630(11) Uiso 0.82 1 d P B 1
H23 H 0.1837 0.9636 0.5315 0.076 Uiso 0.82 1 calc PR B 1
N27 N 0.2171(18) 0.551(2) 0.5524(10) 0.051(4) Uiso 0.18 1 d PD C 2
H27 H 0.2279 0.4608 0.5488 0.062 Uiso 0.18 1 calc PR C 2
C30 C 0.1685(18) 0.8277(19) 0.5618(11) 0.038(3) Uiso 0.18 1 d PD C 2
H30 H 0.1508 0.9223 0.5633 0.045 Uiso 0.18 1 calc PR C 2
C29 C 0.123(2) 0.716(2) 0.6222(14) 0.061(5) Uiso 0.18 1 d PD C 2
H29 H 0.0695 0.7368 0.6695 0.073 Uiso 0.18 1 calc PR C 2
C28 C 0.146(2) 0.579(2) 0.6217(12) 0.054(4) Uiso 0.18 1 d PD C 2
H28 H 0.1137 0.5078 0.6669 0.065 Uiso 0.18 1 calc PR C 2
C32 C 0.274(3) 0.647(2) 0.4881(15) 0.070(6) Uiso 0.18 1 d PD C 2
H32 H 0.3270 0.6248 0.4413 0.085 Uiso 0.18 1 calc PR C 2
C31 C 0.244(4) 0.780(3) 0.4989(18) 0.110(10) Uiso 0.18 1 d PD C 2
C33 C 0.3114 0.8866 0.4422 0.18(2) Uiso 0.18 1 d P C 2
H33A H 0.2431 0.8495 0.3793 0.271 Uiso 0.18 1 calc PR C 2
H33B H 0.4256 0.8984 0.4408 0.271 Uiso 0.18 1 calc PR C 2
H33C H 0.3150 0.9900 0.4648 0.271 Uiso 0.18 1 calc PR C 2
Cl2 Cl 0.2782 0.2016 0.5217 0.177 Uiso 0.18 1 d P D 2


_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 1.6304(19) . ?
Si1 C8 1.867(2) . ?
Si1 C2 1.868(2) . ?
Si1 C14 1.869(3) . ?
O1 H1 0.9733 . ?
C14 C19 1.399(3) . ?
C14 C15 1.404(3) . ?
C8 C13 1.394(4) . ?
C8 C9 1.401(3) . ?
C2 C7 1.398(4) . ?
C2 C3 1.399(4) . ?
C18 C17 1.383(4) . ?
C18 C19 1.391(4) . ?
C18 H18 0.9500 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C13 C12 1.392(4) . ?
C13 H13 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C3 C4 1.393(4) . ?
C3 H3 0.9500 . ?
C7 C6 1.383(4) . ?
C7 H7 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10 0.9500 . ?
C17 C16 1.385(4) . ?
C17 H17 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C12 C11 1.379(4) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C16 H16 0.9500 . ?
C6 C5 1.382(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
N20 C25 1.324(6) . ?
N20 C21 1.345(5) . ?
N20 H20 0.8800 . ?
C21 C22 1.374(6) . ?
C21 C26 1.508(5) . ?
C22 C23 1.380(6) . ?
C22 H22 0.9500 . ?
C25 C24 1.374(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C24 C23 1.341(7) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
N27 C32 1.3401(11) . ?
N27 C28 1.3400(11) . ?
N27 H27 0.8800 . ?
C30 C31 1.3701(11) . ?
C30 C29 1.3702(11) . ?
C30 H30 0.9500 . ?
C29 C28 1.3701(11) . ?
C29 H29 0.9500 . ?
C28 H28 0.9500 . ?
C32 C31 1.3701(11) . ?
C32 H32 0.9500 . ?
C31 C33 1.33(3) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

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 C8 105.87(10) . . ?
O1 Si1 C2 111.65(11) . . ?
C8 Si1 C2 108.39(11) . . ?
O1 Si1 C14 110.59(11) . . ?
C8 Si1 C14 110.96(11) . . ?
C2 Si1 C14 109.33(11) . . ?
Si1 O1 H1 117.9 . . ?
C19 C14 C15 117.1(2) . . ?
C19 C14 Si1 122.41(18) . . ?
C15 C14 Si1 120.53(18) . . ?
C13 C8 C9 117.1(2) . . ?
C13 C8 Si1 122.34(18) . . ?
C9 C8 Si1 120.52(19) . . ?
C7 C2 C3 117.2(2) . . ?
C7 C2 Si1 119.62(19) . . ?
C3 C2 Si1 123.09(19) . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C18 C19 C14 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C12 C13 C8 121.7(2) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C6 C7 C2 121.8(3) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C11 C10 C9 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C17 C16 C15 119.8(2) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C25 N20 C21 123.5(3) . . ?
C25 N20 H20 118.3 . . ?
C21 N20 H20 118.3 . . ?
N20 C21 C22 117.4(4) . . ?
N20 C21 C26 117.7(3) . . ?
C22 C21 C26 125.0(4) . . ?
C21 C22 C23 120.6(4) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
N20 C25 C24 119.1(4) . . ?
N20 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C23 C24 C25 120.3(5) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C23 C22 119.2(5) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C32 N27 C28 127.0(17) . . ?
C32 N27 H27 116.5 . . ?
C28 N27 H27 116.5 . . ?
C31 C30 C29 108.8(19) . . ?
C31 C30 H30 125.6 . . ?
C29 C30 H30 125.6 . . ?
C28 C29 C30 127.1(18) . . ?
C28 C29 H29 116.5 . . ?
C30 C29 H29 116.5 . . ?
N27 C28 C29 114.8(17) . . ?
N27 C28 H28 122.6 . . ?
C29 C28 H28 122.6 . . ?
N27 C32 C31 111(2) . . ?
N27 C32 H32 124.5 . . ?
C31 C32 H32 124.5 . . ?
C33 C31 C30 115.1(18) . . ?
C33 C31 C32 113.4(14) . . ?
C30 C31 C32 131(2) . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

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 Cl1 0.97 2.12 3.091(2) 174.8 .
O1 H1 Cl2 0.97 2.20 3.1134(19) 156.3 .
N20 H20 Cl1 0.88 2.22 3.096(3) 174.1 .
N27 H27 Cl2 0.88 2.63 3.508(16) 173.3 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1481647'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O, C6 H8 N, Cl'
_chemical_formula_sum            'C25 H24 Cl N O'
_chemical_formula_weight         389.90

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'
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

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

_cell_length_a                   8.8297(18)
_cell_length_b                   9.1147(18)
_cell_length_c                   14.282(3)
_cell_angle_alpha                91.02(3)
_cell_angle_beta                 99.85(3)
_cell_angle_gamma                115.48(3)
_cell_volume                     1016.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'NONIUS KAPPA CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28528
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         27.53
_reflns_number_total             4664
_reflns_number_gt                3573
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XSEED
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0551P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4664
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
Cl1 Cl 0.28101(5) 0.79096(4) 0.00820(3) 0.03250(12) Uani 1 1 d . . .
N21 N 0.26014(16) 0.11427(15) 0.02946(9) 0.0302(3) Uani 1 1 d . . .
H21 H 0.2778 0.0263 0.0293 0.036 Uiso 1 1 calc R . .
C22 C 0.17419(18) 0.13505(18) 0.09312(11) 0.0298(3) Uani 1 1 d . . .
C26 C 0.3207(2) 0.2203(2) -0.03402(12) 0.0425(4) Uani 1 1 d . . .
H26 H 0.3832 0.2013 -0.0768 0.051 Uiso 1 1 calc R . .
C24 C 0.2007(3) 0.3805(2) 0.02580(15) 0.0520(5) Uani 1 1 d . . .
H24 H 0.1772 0.4729 0.0240 0.062 Uiso 1 1 calc R . .
C23 C 0.1438(2) 0.2712(2) 0.09083(13) 0.0436(4) Uani 1 1 d . . .
H23 H 0.0827 0.2893 0.1349 0.052 Uiso 1 1 calc R . .
C27 C 0.1209(2) 0.0113(2) 0.16211(13) 0.0449(4) Uani 1 1 d . . .
H27A H 0.0982 -0.0956 0.1322 0.067 Uiso 1 1 calc R . .
H27B H 0.0168 0.0052 0.1809 0.067 Uiso 1 1 calc R . .
H27C H 0.2125 0.0426 0.2188 0.067 Uiso 1 1 calc R . .
C25 C 0.2917(2) 0.3568(2) -0.03675(15) 0.0526(5) Uani 1 1 d . . .
H25 H 0.3339 0.4335 -0.0812 0.063 Uiso 1 1 calc R . .
O1 O 0.58633(13) 0.26836(12) 0.17318(7) 0.0282(2) Uani 1 1 d . . .
C9 C 0.84400(17) 0.43654(16) 0.29057(10) 0.0229(3) Uani 1 1 d . . .
C15 C 0.55287(17) 0.28266(17) 0.33228(10) 0.0240(3) Uani 1 1 d . . .
C2 C 0.67583(17) 0.27862(17) 0.26903(9) 0.0227(3) Uani 1 1 d . . .
C3 C 0.70828(18) 0.12682(17) 0.28214(10) 0.0237(3) Uani 1 1 d . . .
C8 C 0.85944(18) 0.13348(18) 0.33426(10) 0.0279(3) Uani 1 1 d . . .
H8 H 0.9504 0.2362 0.3609 0.034 Uiso 1 1 calc R . .
C10 C 0.90636(18) 0.52594(18) 0.38027(10) 0.0270(3) Uani 1 1 d . . .
H10 H 0.8423 0.4906 0.4294 0.032 Uiso 1 1 calc R . .
C14 C 0.94180(18) 0.49105(17) 0.22028(10) 0.0270(3) Uani 1 1 d . . .
H14 H 0.9018 0.4316 0.1588 0.032 Uiso 1 1 calc R . .
C11 C 1.06127(19) 0.66626(19) 0.39874(11) 0.0320(3) Uani 1 1 d . . .
H11 H 1.1017 0.7263 0.4601 0.038 Uiso 1 1 calc R . .
C16 C 0.52550(19) 0.19647(19) 0.41187(11) 0.0305(3) Uani 1 1 d . . .
H16 H 0.5825 0.1299 0.4281 0.037 Uiso 1 1 calc R . .
C6 C 0.7481(2) -0.15920(19) 0.30991(11) 0.0334(4) Uani 1 1 d . . .
H6 H 0.7614 -0.2562 0.3193 0.040 Uiso 1 1 calc R . .
C12 C 1.1568(2) 0.71885(19) 0.32826(12) 0.0338(4) Uani 1 1 d . . .
H12 H 1.2626 0.8145 0.3411 0.041 Uiso 1 1 calc R . .
C13 C 1.0968(2) 0.63089(19) 0.23879(12) 0.0332(3) Uani 1 1 d . . .
H13 H 1.1618 0.6663 0.1901 0.040 Uiso 1 1 calc R . .
C20 C 0.46754(19) 0.37970(18) 0.31018(11) 0.0304(3) Uani 1 1 d . . .
H20 H 0.4851 0.4401 0.2563 0.036 Uiso 1 1 calc R . .
C5 C 0.5968(2) -0.16708(19) 0.25796(11) 0.0330(3) Uani 1 1 d . . .
H5 H 0.5057 -0.2702 0.2320 0.040 Uiso 1 1 calc R . .
C7 C 0.8795(2) -0.00896(19) 0.34801(11) 0.0329(3) Uani 1 1 d . . .
H7 H 0.9838 -0.0025 0.3836 0.040 Uiso 1 1 calc R . .
C19 C 0.3573(2) 0.3887(2) 0.36619(12) 0.0368(4) Uani 1 1 d . . .
H19 H 0.2992 0.4544 0.3501 0.044 Uiso 1 1 calc R . .
C17 C 0.4154(2) 0.2067(2) 0.46814(12) 0.0367(4) Uani 1 1 d . . .
H17 H 0.3979 0.1473 0.5225 0.044 Uiso 1 1 calc R . .
C4 C 0.57706(19) -0.02566(18) 0.24358(11) 0.0294(3) Uani 1 1 d . . .
H4 H 0.4731 -0.0327 0.2071 0.035 Uiso 1 1 calc R . .
C18 C 0.3317(2) 0.3025(2) 0.44520(12) 0.0377(4) Uani 1 1 d . . .
H18 H 0.2567 0.3093 0.4836 0.045 Uiso 1 1 calc R . .
H1 H 0.6401 0.2436 0.1299 0.068(7) Uiso 1 1 d R . .


_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
N21 C22 1.339(2) . ?
N21 C26 1.340(2) . ?
N21 H21 0.8800 . ?
C22 C23 1.378(2) . ?
C22 C27 1.485(2) . ?
C26 C25 1.374(3) . ?
C26 H26 0.9500 . ?
C24 C25 1.370(3) . ?
C24 C23 1.367(3) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C25 H25 0.9500 . ?
O1 C2 1.4384(16) . ?
O1 H1 0.9199 . ?
C9 C10 1.394(2) . ?
C9 C14 1.395(2) . ?
C9 C2 1.536(2) . ?
C15 C16 1.389(2) . ?
C15 C20 1.397(2) . ?
C15 C2 1.5378(19) . ?
C2 C3 1.5374(19) . ?
C3 C8 1.388(2) . ?
C3 C4 1.395(2) . ?
C8 C7 1.397(2) . ?
C8 H8 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C14 C13 1.390(2) . ?
C14 H14 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C6 C7 1.381(2) . ?
C6 C5 1.385(2) . ?
C6 H6 0.9500 . ?
C12 C13 1.387(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C20 C19 1.388(2) . ?
C20 H20 0.9500 . ?
C5 C4 1.387(2) . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C19 C18 1.381(2) . ?
C19 H19 0.9500 . ?
C17 C18 1.378(2) . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C18 H18 0.9500 . ?

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
C22 N21 C26 123.45(14) . . ?
C22 N21 H21 118.3 . . ?
C26 N21 H21 118.3 . . ?
N21 C22 C23 117.57(15) . . ?
N21 C22 C27 117.74(14) . . ?
C23 C22 C27 124.69(16) . . ?
N21 C26 C25 119.48(17) . . ?
N21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C25 C24 C23 120.04(17) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C23 C22 120.63(17) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C25 C26 118.81(17) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C2 O1 H1 110.2 . . ?
C10 C9 C14 118.16(13) . . ?
C10 C9 C2 121.89(13) . . ?
C14 C9 C2 119.92(12) . . ?
C16 C15 C20 118.39(13) . . ?
C16 C15 C2 122.81(12) . . ?
C20 C15 C2 118.78(13) . . ?
O1 C2 C9 109.99(11) . . ?
O1 C2 C3 109.91(11) . . ?
C9 C2 C3 111.40(11) . . ?
O1 C2 C15 104.21(10) . . ?
C9 C2 C15 110.51(11) . . ?
C3 C2 C15 110.58(11) . . ?
C8 C3 C4 118.36(13) . . ?
C8 C3 C2 123.03(13) . . ?
C4 C3 C2 118.54(12) . . ?
C3 C8 C7 120.84(14) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C11 C10 C9 120.80(14) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C13 C14 C9 121.07(14) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
C12 C11 C10 120.37(14) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C15 C16 C17 120.69(14) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C7 C6 C5 119.40(14) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C11 C12 C13 119.53(14) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.08(15) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C19 C20 C15 120.67(15) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C4 C5 C6 120.52(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C7 C8 120.17(14) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C18 C19 C20 120.21(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C18 C17 C16 120.20(15) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C5 C4 C3 120.70(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C17 C18 C19 119.83(15) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?

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 Cl1 0.92 2.26 3.1478(13) 161.9 2_665
N21 H21 Cl1 0.88 2.17 3.0439(14) 169.7 1_545

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1481648'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H16 O Si), C6 H8 N, Cl'
_chemical_formula_sum            'C42 H40 Cl N O2 Si2'
_chemical_formula_weight         682.38

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

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

_cell_length_a                   10.008(2)
_cell_length_b                   14.177(3)
_cell_length_c                   14.937(3)
_cell_angle_alpha                64.62(3)
_cell_angle_beta                 72.74(3)
_cell_angle_gamma                77.69(3)
_cell_volume                     1819.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4361
_cell_measurement_theta_min      1.55
_cell_measurement_theta_max      26.70

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 apex II duo'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26963
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         26.70
_reflns_number_total             7613
_reflns_number_gt                4631
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0477P)²+0.7227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7613
_refine_ls_number_parameters     501
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.003
_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 0.13203(7) 0.56651(5) 0.15578(5) 0.02811(18) Uani 1 1 d . . .
Si2 Si 0.64660(7) 0.07620(5) 0.63450(5) 0.02813(18) Uani 1 1 d . . .
O1 O 0.16032(18) 0.46902(13) 0.11845(13) 0.0378(4) Uani 1 1 d . . .
H1 H 0.1765 0.4124 0.1665 0.045 Uiso 1 1 calc R . .
O2 O 0.67590(18) -0.01939(13) 0.59508(13) 0.0388(4) Uani 1 1 d . . .
H2 H 0.7139 -0.0730 0.6354 0.047 Uiso 1 1 calc R . .
C9 C 0.0025(2) 0.53940(18) 0.28167(18) 0.0281(5) Uani 1 1 d . . .
C3 C 0.0579(2) 0.68257(19) 0.05657(17) 0.0289(6) Uani 1 1 d . . .
C27 C 0.5190(2) 0.04433(19) 0.76142(18) 0.0298(6) Uani 1 1 d . . .
C15 C 0.3020(2) 0.59640(18) 0.16170(18) 0.0294(6) Uani 1 1 d . . .
C26 C 0.6145(3) 0.2913(2) 0.4975(2) 0.0368(6) Uani 1 1 d . . .
H26 H 0.6866 0.3011 0.5213 0.044 Uiso 1 1 calc R . .
C21 C 0.5701(2) 0.19196(19) 0.53623(17) 0.0275(5) Uani 1 1 d . . .
C33 C 0.8141(2) 0.10627(18) 0.64392(18) 0.0295(6) Uani 1 1 d . . .
C10 C 0.0195(3) 0.4472(2) 0.36711(19) 0.0353(6) Uani 1 1 d . . .
H10 H 0.0982 0.3975 0.3609 0.042 Uiso 1 1 calc R . .
C14 C -0.1147(2) 0.6103(2) 0.29534(19) 0.0344(6) Uani 1 1 d . . .
H14 H -0.1293 0.6737 0.2392 0.041 Uiso 1 1 calc R . .
C8 C -0.0550(3) 0.6740(2) 0.02398(19) 0.0380(6) Uani 1 1 d . . .
H8 H -0.0908 0.6078 0.0511 0.046 Uiso 1 1 calc R . .
C22 C 0.4630(2) 0.1817(2) 0.49924(19) 0.0358(6) Uani 1 1 d . . .
H22 H 0.4301 0.1149 0.5240 0.043 Uiso 1 1 calc R . .
C32 C 0.5423(3) -0.0481(2) 0.8453(2) 0.0376(6) Uani 1 1 d . . .
H32 H 0.6239 -0.0949 0.8369 0.045 Uiso 1 1 calc R . .
C4 C 0.1064(3) 0.7811(2) 0.01485(19) 0.0354(6) Uani 1 1 d . . .
H4 H 0.1826 0.7900 0.0352 0.042 Uiso 1 1 calc R . .
C20 C 0.4261(3) 0.5846(2) 0.0914(2) 0.0417(7) Uani 1 1 d . . .
H20 H 0.4236 0.5572 0.0441 0.050 Uiso 1 1 calc R . .
C6 C -0.0650(3) 0.8554(2) -0.0864(2) 0.0430(7) Uani 1 1 d . . .
H6 H -0.1064 0.9141 -0.1349 0.052 Uiso 1 1 calc R . .
C11 C -0.0756(3) 0.4273(2) 0.4600(2) 0.0413(7) Uani 1 1 d . . .
H11 H -0.0622 0.3641 0.5166 0.050 Uiso 1 1 calc R . .
C34 C 0.9355(3) 0.1136(2) 0.5658(2) 0.0439(7) Uani 1 1 d . . .
H34 H 0.9322 0.1014 0.5088 0.053 Uiso 1 1 calc R . .
C23 C 0.4041(3) 0.2666(2) 0.4276(2) 0.0411(7) Uani 1 1 d . . .
H23 H 0.3309 0.2580 0.4041 0.049 Uiso 1 1 calc R . .
C7 C -0.1160(3) 0.7591(2) -0.0467(2) 0.0422(7) Uani 1 1 d . . .
H7 H -0.1924 0.7511 -0.0676 0.051 Uiso 1 1 calc R . .
C28 C 0.3974(3) 0.1104(2) 0.77844(19) 0.0352(6) Uani 1 1 d . . .
H28 H 0.3781 0.1735 0.7236 0.042 Uiso 1 1 calc R . .
C12 C -0.1900(3) 0.4987(2) 0.4709(2) 0.0384(6) Uani 1 1 d . . .
H12 H -0.2550 0.4849 0.5349 0.046 Uiso 1 1 calc R . .
C38 C 0.8246(3) 0.12462(19) 0.72600(19) 0.0333(6) Uani 1 1 d . . .
H38 H 0.7442 0.1208 0.7803 0.040 Uiso 1 1 calc R . .
C16 C 0.3110(3) 0.63561(19) 0.23041(19) 0.0337(6) Uani 1 1 d . . .
H16 H 0.2288 0.6445 0.2792 0.040 Uiso 1 1 calc R . .
C30 C 0.3304(3) -0.0054(2) 0.9535(2) 0.0456(7) Uani 1 1 d . . .
H30 H 0.2666 -0.0222 1.0183 0.055 Uiso 1 1 calc R . .
C25 C 0.5561(3) 0.3768(2) 0.4248(2) 0.0435(7) Uani 1 1 d . . .
H25 H 0.5885 0.4439 0.3993 0.052 Uiso 1 1 calc R . .
C17 C 0.4379(3) 0.6620(2) 0.2290(2) 0.0430(7) Uani 1 1 d . . .
H17 H 0.4418 0.6885 0.2767 0.052 Uiso 1 1 calc R . .
C24 C 0.4515(3) 0.3638(2) 0.3901(2) 0.0411(7) Uani 1 1 d . . .
H24 H 0.4117 0.4219 0.3403 0.049 Uiso 1 1 calc R . .
C5 C 0.0454(3) 0.8667(2) -0.0562(2) 0.0448(7) Uani 1 1 d . . .
H5 H 0.0802 0.9333 -0.0838 0.054 Uiso 1 1 calc R . .
C37 C 0.9496(3) 0.1483(2) 0.7304(2) 0.0421(7) Uani 1 1 d . . .
H37 H 0.9543 0.1595 0.7877 0.051 Uiso 1 1 calc R . .
C13 C -0.2098(3) 0.5905(2) 0.3884(2) 0.0410(7) Uani 1 1 d . . .
H13 H -0.2886 0.6398 0.3956 0.049 Uiso 1 1 calc R . .
C29 C 0.3045(3) 0.0863(2) 0.8729(2) 0.0437(7) Uani 1 1 d . . .
H29 H 0.2230 0.1329 0.8823 0.052 Uiso 1 1 calc R . .
C31 C 0.4495(3) -0.0725(2) 0.9395(2) 0.0452(7) Uani 1 1 d . . .
H31 H 0.4675 -0.1356 0.9948 0.054 Uiso 1 1 calc R . .
C19 C 0.5523(3) 0.6118(2) 0.0891(2) 0.0521(8) Uani 1 1 d . . .
H19 H 0.6347 0.6045 0.0397 0.062 Uiso 1 1 calc R . .
C35 C 1.0600(3) 0.1381(3) 0.5691(2) 0.0547(8) Uani 1 1 d . . .
H35 H 1.1406 0.1428 0.5147 0.066 Uiso 1 1 calc R . .
C36 C 1.0670(3) 0.1556(2) 0.6517(2) 0.0476(8) Uani 1 1 d . . .
H36 H 1.1523 0.1725 0.6543 0.057 Uiso 1 1 calc R . .
C18 C 0.5576(3) 0.6498(2) 0.1590(2) 0.0488(8) Uani 1 1 d . . .
H18 H 0.6442 0.6675 0.1585 0.059 Uiso 1 1 calc R . .
Cl1 Cl 0.17973(12) 0.23194(6) 0.27597(7) 0.0756(3) Uani 1 1 d . . .
C39A C 0.6609(14) 0.2757(11) 0.2127(14) 0.051(4) Uani 0.55 1 d P A 1
H39A H 0.6006 0.3334 0.1791 0.062 Uiso 0.55 1 calc PR A 1
C44A C 0.7807(8) 0.2960(5) 0.2225(5) 0.0406(14) Uani 0.55 1 d P A 1
C41A C 0.7104(7) 0.0930(6) 0.2981(5) 0.0647(19) Uani 0.55 1 d P A 1
H41A H 0.6863 0.0231 0.3258 0.078 Uiso 0.55 1 calc PR A 1
C40A C 0.6216(7) 0.1768(7) 0.2486(6) 0.0604(19) Uani 0.55 1 d P A 1
H40A H 0.5367 0.1658 0.2399 0.073 Uiso 0.55 1 calc PR A 1
N43A N 0.8656(13) 0.2119(7) 0.2695(9) 0.052(3) Uani 0.55 1 d P A 1
H43A H 0.9449 0.2222 0.2764 0.062 Uiso 0.55 1 calc PR A 1
C45A C 0.8265(7) 0.4005(5) 0.1865(6) 0.070(2) Uani 0.55 1 d P A 1
H45A H 0.7948 0.4256 0.2419 0.105 Uiso 0.55 1 calc PR A 1
H45B H 0.7859 0.4491 0.1289 0.105 Uiso 0.55 1 calc PR A 1
H45C H 0.9293 0.3965 0.1648 0.105 Uiso 0.55 1 calc PR A 1
C52B C 0.8660(8) 0.3263(8) 0.2058(6) 0.068(3) Uani 0.45 1 d PD B 2
H52B H 0.9241 0.3818 0.1778 0.081 Uiso 0.45 1 calc PR B 2
C50B C 0.5305(8) 0.2738(7) 0.1791(6) 0.075(2) Uani 0.45 1 d P B 2
H50A H 0.5552 0.2557 0.1193 0.113 Uiso 0.45 1 calc PR B 2
H50B H 0.4890 0.3468 0.1606 0.113 Uiso 0.45 1 calc PR B 2
H50C H 0.4626 0.2274 0.2335 0.113 Uiso 0.45 1 calc PR B 2
C51B C 0.7457(8) 0.3385(8) 0.1743(8) 0.058(2) Uani 0.45 1 d PD B 2
H51B H 0.7224 0.4032 0.1225 0.070 Uiso 0.45 1 calc PR B 2
N46B N 0.8991(16) 0.2337(8) 0.2772(11) 0.069(4) Uani 0.45 1 d PD B 2
H46B H 0.9766 0.2248 0.2975 0.082 Uiso 0.45 1 calc PR B 2
C47B C 0.8189(12) 0.1539(10) 0.3190(10) 0.076(4) Uani 0.45 1 d PD B 2
H47B H 0.8454 0.0889 0.3691 0.091 Uiso 0.45 1 calc PR B 2
C48B C 0.6978(10) 0.1684(7) 0.2877(6) 0.069(3) Uani 0.45 1 d PD B 2
H48B H 0.6397 0.1126 0.3176 0.083 Uiso 0.45 1 calc PR B 2
C49B C 0.6578(18) 0.2609(10) 0.2147(14) 0.050(6) Uani 0.45 1 d PD B 2
C42A C 0.8319(11) 0.1129(8) 0.3059(8) 0.062(3) Uani 0.55 1 d P A 1
H42A H 0.8946 0.0560 0.3378 0.074 Uiso 0.55 1 calc PR A 1


_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 1.6435(18) . ?
Si1 C3 1.870(3) . ?
Si1 C15 1.873(2) . ?
Si1 C9 1.874(3) . ?
Si2 O2 1.6375(18) . ?
Si2 C21 1.871(3) . ?
Si2 C27 1.872(3) . ?
Si2 C33 1.873(2) . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?
C9 C14 1.400(3) . ?
C9 C10 1.404(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.402(3) . ?
C27 C28 1.399(3) . ?
C27 C32 1.406(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.400(3) . ?
C26 C21 1.390(3) . ?
C26 C25 1.392(3) . ?
C26 H26 0.9500 . ?
C21 C22 1.401(3) . ?
C33 C38 1.394(3) . ?
C33 C34 1.399(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C14 C13 1.382(3) . ?
C14 H14 0.9500 . ?
C8 C7 1.385(3) . ?
C8 H8 0.9500 . ?
C22 C23 1.382(3) . ?
C22 H22 0.9500 . ?
C32 C31 1.381(4) . ?
C32 H32 0.9500 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9500 . ?
C20 C19 1.384(4) . ?
C20 H20 0.9500 . ?
C6 C5 1.373(4) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9500 . ?
C11 C12 1.377(4) . ?
C11 H11 0.9500 . ?
C34 C35 1.382(4) . ?
C34 H34 0.9500 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9500 . ?
C7 H7 0.9500 . ?
C28 C29 1.384(3) . ?
C28 H28 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C38 C37 1.389(3) . ?
C38 H38 0.9500 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9500 . ?
C30 C29 1.381(4) . ?
C30 C31 1.381(4) . ?
C30 H30 0.9500 . ?
C25 C24 1.373(4) . ?
C25 H25 0.9500 . ?
C17 C18 1.372(4) . ?
C17 H17 0.9500 . ?
C24 H24 0.9500 . ?
C5 H5 0.9500 . ?
C37 C36 1.379(4) . ?
C37 H37 0.9500 . ?
C13 H13 0.9500 . ?
C29 H29 0.9500 . ?
C31 H31 0.9500 . ?
C19 C18 1.382(4) . ?
C19 H19 0.9500 . ?
C35 C36 1.383(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C18 H18 0.9500 . ?
C39A C44A 1.353(12) . ?
C39A C40A 1.369(13) . ?
C39A H39A 0.9500 . ?
C44A N43A 1.357(11) . ?
C44A C45A 1.468(8) . ?
C41A C42A 1.353(11) . ?
C41A C40A 1.391(11) . ?
C41A H41A 0.9500 . ?
C40A H40A 0.9500 . ?
N43A C42A 1.348(13) . ?
N43A H43A 0.8800 . ?
C45A H45A 0.9800 . ?
C45A H45B 0.9800 . ?
C45A H45C 0.9800 . ?
C52B N46B 1.3400(12) . ?
C52B C51B 1.3698(11) . ?
C52B H52B 0.9500 . ?
C50B C49B 1.470(13) . ?
C50B H50A 0.9800 . ?
C50B H50B 0.9800 . ?
C50B H50C 0.9800 . ?
C51B C49B 1.3700(12) . ?
C51B H51B 0.9500 . ?
N46B C47B 1.3400(12) . ?
N46B H46B 0.8800 . ?
C47B C48B 1.3699(11) . ?
C47B H47B 0.9500 . ?
C48B C49B 1.3699(12) . ?
C48B H48B 0.9500 . ?
C42A H42A 0.9500 . ?

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 C3 106.20(10) . . ?
O1 Si1 C15 110.07(10) . . ?
C3 Si1 C15 109.00(11) . . ?
O1 Si1 C9 112.44(10) . . ?
C3 Si1 C9 108.72(11) . . ?
C15 Si1 C9 110.27(11) . . ?
O2 Si2 C21 105.45(10) . . ?
O2 Si2 C27 111.77(11) . . ?
C21 Si2 C27 109.63(11) . . ?
O2 Si2 C33 110.94(10) . . ?
C21 Si2 C33 110.10(11) . . ?
C27 Si2 C33 108.90(11) . . ?
Si1 O1 H1 109.5 . . ?
Si2 O2 H2 109.5 . . ?
C14 C9 C10 116.9(2) . . ?
C14 C9 Si1 121.76(19) . . ?
C10 C9 Si1 121.36(18) . . ?
C4 C3 C8 116.9(2) . . ?
C4 C3 Si1 122.75(19) . . ?
C8 C3 Si1 120.25(18) . . ?
C28 C27 C32 116.6(2) . . ?
C28 C27 Si2 122.47(19) . . ?
C32 C27 Si2 120.92(19) . . ?
C16 C15 C20 117.1(2) . . ?
C16 C15 Si1 122.94(18) . . ?
C20 C15 Si1 119.9(2) . . ?
C21 C26 C25 121.7(2) . . ?
C21 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C21 C22 117.0(2) . . ?
C26 C21 Si2 122.32(18) . . ?
C22 C21 Si2 120.66(18) . . ?
C38 C33 C34 116.7(2) . . ?
C38 C33 Si2 122.83(18) . . ?
C34 C33 Si2 120.4(2) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C13 C14 C9 121.7(2) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C7 C8 C3 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
C23 C22 C21 121.4(2) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C31 C32 C27 121.6(3) . . ?
C31 C32 H32 119.2 . . ?
C27 C32 H32 119.2 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C19 C20 C15 121.8(3) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C35 C34 C33 122.0(3) . . ?
C35 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C6 C7 C8 119.5(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C29 C28 C27 121.9(2) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C37 C38 C33 121.7(2) . . ?
C37 C38 H38 119.2 . . ?
C33 C38 H38 119.2 . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C29 C30 C31 119.7(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C24 C25 C26 119.8(2) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C36 C37 C38 120.0(3) . . ?
C36 C37 H37 120.0 . . ?
C38 C37 H37 120.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C30 C29 C28 120.0(3) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C37 C36 C35 119.7(2) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C44A C39A C40A 123.7(10) . . ?
C44A C39A H39A 118.1 . . ?
C40A C39A H39A 118.1 . . ?
C39A C44A N43A 116.7(8) . . ?
C39A C44A C45A 125.7(9) . . ?
N43A C44A C45A 117.6(7) . . ?
C42A C41A C40A 118.7(8) . . ?
C42A C41A H41A 120.6 . . ?
C40A C41A H41A 120.6 . . ?
C39A C40A C41A 117.7(9) . . ?
C39A C40A H40A 121.2 . . ?
C41A C40A H40A 121.2 . . ?
C42A N43A C44A 121.9(9) . . ?
C42A N43A H43A 119.0 . . ?
C44A N43A H43A 119.0 . . ?
N46B C52B C51B 118.0(11) . . ?
N46B C52B H52B 121.0 . . ?
C51B C52B H52B 121.0 . . ?
C49B C50B H50A 109.5 . . ?
C49B C50B H50B 109.5 . . ?
H50A C50B H50B 109.5 . . ?
C49B C50B H50C 109.5 . . ?
H50A C50B H50C 109.5 . . ?
H50B C50B H50C 109.5 . . ?
C52B C51B C49B 122.5(11) . . ?
C52B C51B H51B 118.8 . . ?
C49B C51B H51B 118.8 . . ?
C52B N46B C47B 122.6(12) . . ?
C52B N46B H46B 118.7 . . ?
C47B N46B H46B 118.7 . . ?
N46B C47B C48B 118.4(12) . . ?
N46B C47B H47B 120.8 . . ?
C48B C47B H47B 120.8 . . ?
C49B C48B C47B 122.1(11) . . ?
C49B C48B H48B 119.0 . . ?
C47B C48B H48B 119.0 . . ?
C48B C49B C51B 116.4(11) . . ?
C48B C49B C50B 121.4(8) . . ?
C51B C49B C50B 122.2(8) . . ?
N43A C42A C41A 121.3(10) . . ?
N43A C42A H42A 119.4 . . ?
C41A C42A H42A 119.4 . . ?

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 Cl1 0.84 2.37 3.176(2) 160.2 .
N43A H43A Cl1 0.88 2.38 3.250(10) 169.3 1_655
N46B H46B Cl1 0.88 1.98 2.798(13) 154.2 1_655

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.70
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.913
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1481649'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O, C6 H8 N, Cl, H2 O'
_chemical_formula_sum            'C25 H26 Cl N O2'
_chemical_formula_weight         407.92

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'
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

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

_cell_length_a                   8.5764(17)
_cell_length_b                   8.9494(18)
_cell_length_c                   15.567(3)
_cell_angle_alpha                89.44(3)
_cell_angle_beta                 85.34(3)
_cell_angle_gamma                63.17(3)
_cell_volume                     1062.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4217
_cell_measurement_theta_min      1.31
_cell_measurement_theta_max      28.31

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 APEX II DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28589
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         28.35
_reflns_number_total             5297
_reflns_number_gt                4217
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0448P)²+0.3626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    NOREF
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5297
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Cl1 Cl 0.26477(5) 0.95368(5) 0.44156(3) 0.03750(12) Uani 1 1 d . . .
O1 O 0.64971(13) 0.21035(12) 0.30033(6) 0.0246(2) Uani 1 1 d . . .
H1 H 0.6478 0.1198 0.3134 0.030 Uiso 1 1 calc R . .
C3 C 0.88314(16) 0.04037(16) 0.19114(9) 0.0190(3) Uani 1 1 d . . .
C15 C 0.74135(17) 0.35813(16) 0.20026(9) 0.0194(3) Uani 1 1 d . . .
C2 C 0.71175(17) 0.20198(16) 0.21107(8) 0.0190(3) Uani 1 1 d . . .
C20 C 0.88296(18) 0.35822(17) 0.14997(9) 0.0239(3) Uani 1 1 d . . .
H20 H 0.9670 0.2578 0.1209 0.029 Uiso 1 1 calc R . .
C8 C 0.92940(17) -0.03903(17) 0.11017(9) 0.0226(3) Uani 1 1 d . . .
H8 H 0.8537 0.0071 0.0655 0.027 Uiso 1 1 calc R . .
C14 C 0.53466(18) 0.30079(18) 0.07859(9) 0.0245(3) Uani 1 1 d . . .
H14 H 0.5906 0.3694 0.0645 0.029 Uiso 1 1 calc R . .
N21 N 0.93612(19) 0.28894(17) 0.49713(10) 0.0361(3) Uani 1 1 d . . .
C9 C 0.57202(16) 0.20751(16) 0.15301(9) 0.0200(3) Uani 1 1 d . . .
C16 C 0.61889(18) 0.50796(17) 0.24183(10) 0.0247(3) Uani 1 1 d . . .
H16 H 0.5204 0.5107 0.2757 0.030 Uiso 1 1 calc R . .
C7 C 1.08552(19) -0.18551(18) 0.09375(10) 0.0272(3) Uani 1 1 d . . .
H7 H 1.1152 -0.2386 0.0382 0.033 Uiso 1 1 calc R . .
C4 C 0.99825(18) -0.02882(18) 0.25542(10) 0.0260(3) Uani 1 1 d . . .
H4 H 0.9698 0.0245 0.3109 0.031 Uiso 1 1 calc R . .
C19 C 0.9029(2) 0.50415(19) 0.14183(10) 0.0286(3) Uani 1 1 d . . .
H19 H 0.9998 0.5027 0.1069 0.034 Uiso 1 1 calc R . .
C10 C 0.48662(18) 0.10891(18) 0.17242(10) 0.0266(3) Uani 1 1 d . . .
H10 H 0.5101 0.0449 0.2230 0.032 Uiso 1 1 calc R . .
C17 C 0.6396(2) 0.65299(18) 0.23418(10) 0.0294(3) Uani 1 1 d . . .
H17 H 0.5558 0.7537 0.2631 0.035 Uiso 1 1 calc R . .
C13 C 0.41579(19) 0.2942(2) 0.02457(10) 0.0309(3) Uani 1 1 d . . .
H13 H 0.3919 0.3578 -0.0262 0.037 Uiso 1 1 calc R . .
C18 C 0.7821(2) 0.65106(18) 0.18440(10) 0.0301(3) Uani 1 1 d . . .
H18 H 0.7968 0.7499 0.1795 0.036 Uiso 1 1 calc R . .
C6 C 1.19758(19) -0.25394(18) 0.15835(10) 0.0296(3) Uani 1 1 d . . .
H6 H 1.3035 -0.3543 0.1473 0.036 Uiso 1 1 calc R . .
C11 C 0.3675(2) 0.1032(2) 0.11857(11) 0.0324(4) Uani 1 1 d . . .
H11 H 0.3100 0.0358 0.1326 0.039 Uiso 1 1 calc R . .
C25 C 0.8291(2) 0.5175(2) 0.59678(10) 0.0312(3) Uani 1 1 d . . .
C24 C 0.6920(2) 0.6024(2) 0.54501(11) 0.0339(4) Uani 1 1 d . . .
H24 H 0.6062 0.7129 0.5614 0.041 Uiso 1 1 calc R . .
C12 C 0.33260(19) 0.1959(2) 0.04448(11) 0.0327(4) Uani 1 1 d . . .
H12 H 0.2517 0.1917 0.0075 0.039 Uiso 1 1 calc R . .
C5 C 1.15414(19) -0.17516(19) 0.23883(10) 0.0302(3) Uani 1 1 d . . .
H5 H 1.2311 -0.2211 0.2831 0.036 Uiso 1 1 calc R . .
C27 C 0.9516(2) 0.3578(2) 0.56954(11) 0.0317(3) Uani 1 1 d . . .
H27 H 1.0477 0.2964 0.6027 0.038 Uiso 1 1 calc R . .
C23 C 0.6791(2) 0.5282(2) 0.47026(11) 0.0375(4) Uani 1 1 d . . .
H23 H 0.5856 0.5873 0.4353 0.045 Uiso 1 1 calc R . .
C22 C 0.8027(2) 0.3686(2) 0.44720(12) 0.0388(4) Uani 1 1 d . . .
H22 H 0.7946 0.3146 0.3967 0.047 Uiso 1 1 calc R . .
C26 C 0.8447(3) 0.5957(3) 0.67842(12) 0.0487(5) Uani 1 1 d . . .
H26A H 0.7643 0.5877 0.7246 0.073 Uiso 1 1 calc R . .
H26B H 0.8145 0.7138 0.6693 0.073 Uiso 1 1 calc R . .
H26C H 0.9653 0.5367 0.6947 0.073 Uiso 1 1 calc R . .
O2 O 0.63671(17) -0.05543(15) 0.38609(8) 0.0351(3) Uani 1 1 d . . .
H2A H 0.659(3) -0.025(3) 0.4347(15) 0.058(7) Uiso 1 1 d . . .
H2B H 0.534(3) -0.050(3) 0.3987(16) 0.067(7) Uiso 1 1 d . . .
H21 H 1.027(3) 0.178(3) 0.4783(15) 0.065(7) 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
O1 C2 1.4370(17) . ?
O1 H1 0.8400 . ?
C3 C8 1.390(2) . ?
C3 C4 1.3985(19) . ?
C3 C2 1.5376(19) . ?
C15 C20 1.391(2) . ?
C15 C16 1.398(2) . ?
C15 C2 1.5344(19) . ?
C2 C9 1.5417(18) . ?
C20 C19 1.395(2) . ?
C20 H20 0.9500 . ?
C8 C7 1.394(2) . ?
C8 H8 0.9500 . ?
C14 C13 1.394(2) . ?
C14 C9 1.393(2) . ?
C14 H14 0.9500 . ?
N21 C27 1.334(2) . ?
N21 C22 1.349(2) . ?
N21 H21 0.97(2) . ?
C9 C10 1.396(2) . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C7 C6 1.387(2) . ?
C7 H7 0.9500 . ?
C4 C5 1.393(2) . ?
C4 H4 0.9500 . ?
C19 C18 1.385(2) . ?
C19 H19 0.9500 . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C13 C12 1.380(2) . ?
C13 H13 0.9500 . ?
C18 H18 0.9500 . ?
C6 C5 1.382(2) . ?
C6 H6 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C25 C27 1.382(2) . ?
C25 C24 1.394(2) . ?
C25 C26 1.501(2) . ?
C24 C23 1.382(2) . ?
C24 H24 0.9500 . ?
C12 H12 0.9500 . ?
C5 H5 0.9500 . ?
C27 H27 0.9500 . ?
C23 C22 1.369(3) . ?
C23 H23 0.9500 . ?
C22 H22 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O2 H2A 0.87(2) . ?
O2 H2B 0.87(3) . ?

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
C2 O1 H1 109.5 . . ?
C8 C3 C4 118.42(12) . . ?
C8 C3 C2 121.94(12) . . ?
C4 C3 C2 119.63(12) . . ?
C20 C15 C16 118.44(13) . . ?
C20 C15 C2 123.05(12) . . ?
C16 C15 C2 118.50(12) . . ?
O1 C2 C15 104.09(11) . . ?
O1 C2 C3 110.25(11) . . ?
C15 C2 C3 111.45(11) . . ?
O1 C2 C9 110.14(11) . . ?
C15 C2 C9 111.00(11) . . ?
C3 C2 C9 109.79(11) . . ?
C15 C20 C19 120.71(14) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C3 C8 C7 120.84(13) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C13 C14 C9 120.55(14) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C27 N21 C22 122.79(15) . . ?
C27 N21 H21 118.8(13) . . ?
C22 N21 H21 118.4(13) . . ?
C10 C9 C14 118.45(13) . . ?
C10 C9 C2 119.33(12) . . ?
C14 C9 C2 122.11(12) . . ?
C17 C16 C15 120.80(14) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C6 C7 C8 120.18(14) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C5 C4 C3 120.61(14) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C18 C19 C20 120.25(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C11 C10 C9 120.85(14) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C18 C17 C16 120.18(14) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C12 C13 C14 120.35(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C19 C18 C17 119.61(14) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C5 C6 C7 119.56(13) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C12 C11 C10 120.00(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C27 C25 C24 117.20(15) . . ?
C27 C25 C26 121.06(15) . . ?
C24 C25 C26 121.74(15) . . ?
C23 C24 C25 121.02(15) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C13 C12 C11 119.79(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C6 C5 C4 120.39(14) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N21 C27 C25 120.62(15) . . ?
N21 C27 H27 119.7 . . ?
C25 C27 H27 119.7 . . ?
C22 C23 C24 119.23(16) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N21 C22 C23 119.12(16) . . ?
N21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H2A O2 H2B 102(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
O1 H1 O2 0.84 1.96 2.7578(17) 158.7 .
O2 H2A Cl1 0.87(2) 2.27(2) 3.1387(16) 176(2) 2_666
O2 H2B Cl1 0.87(3) 2.33(3) 3.2011(16) 176(2) 1_545
N21 H21 Cl1 0.97(2) 2.16(2) 3.117(2) 168(2) 1_645

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1481650'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C18 H16 O Si), C6 H8 N, Cl'
_chemical_formula_sum            'C42 H40 Cl N O2 Si2'
_chemical_formula_weight         682.38

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

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

_cell_length_a                   8.7610(18)
_cell_length_b                   9.6081(19)
_cell_length_c                   23.756(5)
_cell_angle_alpha                91.94(3)
_cell_angle_beta                 93.39(3)
_cell_angle_gamma                113.90(3)
_cell_volume                     1821.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6927
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 apex II duo'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            46660
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.36
_reflns_number_total             9092
_reflns_number_gt                6927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0718P)²+0.8830P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9092
_refine_ls_number_parameters     430
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1410
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.28367(6) 1.20687(5) 0.639603(19) 0.02723(12) Uani 1 1 d . . .
Si2 Si 0.72598(6) 0.78483(5) 0.858503(19) 0.02865(12) Uani 1 1 d . . .
Cl1 Cl 0.53280(10) 1.00491(6) 0.74366(2) 0.0726(2) Uani 1 1 d . . .
O1 O 0.35087(17) 1.21201(15) 0.70592(5) 0.0395(3) Uani 1 1 d . . .
O2 O 0.66467(18) 0.77297(15) 0.79133(5) 0.0413(3) Uani 1 1 d . . .
C7 C 0.2407(2) 1.38107(17) 0.63303(7) 0.0286(3) Uani 1 1 d . . .
C1 C 0.0865(2) 1.03213(17) 0.62117(7) 0.0293(3) Uani 1 1 d . . .
C13 C 0.4463(2) 1.21381(17) 0.59075(7) 0.0275(3) Uani 1 1 d . . .
C25 C 0.7665(2) 0.61102(18) 0.86971(7) 0.0296(3) Uani 1 1 d . . .
C31 C 0.9231(2) 0.96131(18) 0.87562(7) 0.0320(4) Uani 1 1 d . . .
C19 C 0.5633(2) 0.78636(18) 0.90587(7) 0.0293(3) Uani 1 1 d . . .
C6 C 0.0518(2) 0.95096(19) 0.56894(7) 0.0326(4) Uani 1 1 d . . .
H6 H 0.1326 0.9824 0.5418 0.039 Uiso 1 1 calc R . .
C8 C 0.0944(2) 1.3765(2) 0.60506(8) 0.0353(4) Uani 1 1 d . . .
H8 H 0.0120 1.2816 0.5894 0.042 Uiso 1 1 calc R . .
C14 C 0.5219(2) 1.10978(19) 0.59353(8) 0.0349(4) Uani 1 1 d . . .
H14 H 0.4898 1.0349 0.6207 0.042 Uiso 1 1 calc R . .
C32 C 0.9604(2) 1.04183(19) 0.92801(8) 0.0351(4) Uani 1 1 d . . .
H32 H 0.8829 1.0079 0.9561 0.042 Uiso 1 1 calc R . .
C12 C 0.3593(2) 1.5237(2) 0.65514(8) 0.0376(4) Uani 1 1 d . . .
H12 H 0.4606 1.5304 0.6743 0.045 Uiso 1 1 calc R . .
C15 C 0.6425(2) 1.1142(2) 0.55738(9) 0.0406(4) Uani 1 1 d . . .
H15 H 0.6925 1.0433 0.5602 0.049 Uiso 1 1 calc R . .
C23 C 0.3705(3) 0.8937(2) 0.93541(9) 0.0444(5) Uani 1 1 d . . .
H23 H 0.3212 0.9646 0.9305 0.053 Uiso 1 1 calc R . .
C27 C 0.6750(3) 0.3362(2) 0.85536(9) 0.0431(4) Uani 1 1 d . . .
H27 H 0.5938 0.2403 0.8401 0.052 Uiso 1 1 calc R . .
C18 C 0.4971(2) 1.3212(2) 0.54978(8) 0.0348(4) Uani 1 1 d . . .
H18 H 0.4484 1.3930 0.5468 0.042 Uiso 1 1 calc R . .
C24 C 0.4890(2) 0.8905(2) 0.89976(8) 0.0378(4) Uani 1 1 d . . .
H24 H 0.5204 0.9599 0.8707 0.045 Uiso 1 1 calc R . .
C16 C 0.6900(2) 1.2221(2) 0.51724(8) 0.0399(4) Uani 1 1 d . . .
H16 H 0.7723 1.2251 0.4925 0.048 Uiso 1 1 calc R . .
C28 C 0.8187(3) 0.3452(2) 0.88550(9) 0.0435(5) Uani 1 1 d . . .
H28 H 0.8372 0.2554 0.8905 0.052 Uiso 1 1 calc R . .
C30 C 0.9089(2) 0.6163(2) 0.90042(8) 0.0358(4) Uani 1 1 d . . .
H30 H 0.9899 0.7115 0.9164 0.043 Uiso 1 1 calc R . .
C5 C -0.0986(2) 0.8247(2) 0.55564(9) 0.0411(4) Uani 1 1 d . . .
H5 H -0.1189 0.7702 0.5199 0.049 Uiso 1 1 calc R . .
C22 C 0.3236(2) 0.7937(2) 0.97814(9) 0.0437(4) Uani 1 1 d . . .
H22 H 0.2428 0.7963 1.0026 0.052 Uiso 1 1 calc R . .
C17 C 0.6173(2) 1.3253(2) 0.51332(8) 0.0411(4) Uani 1 1 d . . .
H17 H 0.6494 1.3991 0.4857 0.049 Uiso 1 1 calc R . .
C11 C 0.3318(3) 1.6551(2) 0.64959(9) 0.0426(4) Uani 1 1 d . . .
H11 H 0.4139 1.7507 0.6648 0.051 Uiso 1 1 calc R . .
C9 C 0.0665(3) 1.5086(2) 0.59962(9) 0.0448(5) Uani 1 1 d . . .
H9 H -0.0343 1.5033 0.5805 0.054 Uiso 1 1 calc R . .
C10 C 0.1856(3) 1.6470(2) 0.62206(9) 0.0428(4) Uani 1 1 d . . .
H10 H 0.1665 1.7369 0.6185 0.051 Uiso 1 1 calc R . .
C33 C 1.1090(3) 1.1711(2) 0.94018(9) 0.0434(4) Uani 1 1 d . . .
H33 H 1.1315 1.2245 0.9762 0.052 Uiso 1 1 calc R . .
C29 C 0.9351(3) 0.4838(2) 0.90825(9) 0.0453(5) Uani 1 1 d . . .
H29 H 1.0333 0.4895 0.9293 0.054 Uiso 1 1 calc R . .
C21 C 0.3948(3) 0.6901(2) 0.98508(9) 0.0434(4) Uani 1 1 d . . .
H21 H 0.3629 0.6214 1.0143 0.052 Uiso 1 1 calc R . .
C20 C 0.5131(2) 0.6865(2) 0.94931(8) 0.0364(4) Uani 1 1 d . . .
H20 H 0.5611 0.6146 0.9544 0.044 Uiso 1 1 calc R . .
C26 C 0.6499(2) 0.4679(2) 0.84756(8) 0.0383(4) Uani 1 1 d . . .
H26 H 0.5509 0.4608 0.8266 0.046 Uiso 1 1 calc R . .
C34 C 1.2233(3) 1.2217(2) 0.89996(10) 0.0491(5) Uani 1 1 d . . .
H34 H 1.3248 1.3096 0.9083 0.059 Uiso 1 1 calc R . .
C4 C -0.2185(3) 0.7784(2) 0.59428(10) 0.0474(5) Uani 1 1 d . . .
H4 H -0.3213 0.6926 0.5851 0.057 Uiso 1 1 calc R . .
C2 C -0.0372(3) 0.9815(2) 0.65961(9) 0.0490(5) Uani 1 1 d . . .
H7 H -0.0172 1.0338 0.6958 0.059 Uiso 1 1 calc R . .
C36 C 1.0414(3) 1.0158(2) 0.83565(9) 0.0482(5) Uani 1 1 d . . .
H36 H 1.0197 0.9634 0.7995 0.058 Uiso 1 1 calc R . .
C35 C 1.1896(3) 1.1443(3) 0.84760(10) 0.0569(6) Uani 1 1 d . . .
H35 H 1.2678 1.1789 0.8197 0.068 Uiso 1 1 calc R . .
C3 C -0.1884(3) 0.8569(3) 0.64609(11) 0.0589(6) Uani 1 1 d . . .
H3 H -0.2711 0.8259 0.6726 0.071 Uiso 1 1 calc R . .
N37A N 0.8157(6) 0.3265(6) 0.7288(2) 0.0574(12) Uiso 0.56 1 d P A 1
H37A H 0.7414 0.2316 0.7228 0.069 Uiso 0.56 1 calc PR A 1
C39A C 1.0865(5) 0.5062(5) 0.76656(16) 0.0395(8) Uiso 0.56 1 d P A 1
C41A C 1.0409(5) 0.6202(5) 0.74919(17) 0.0451(9) Uiso 0.56 1 d P A 1
H41A H 1.1156 0.7244 0.7560 0.054 Uiso 0.56 1 calc PR A 1
C42A C 0.8821(8) 0.5794(7) 0.7212(3) 0.0704(15) Uiso 0.56 1 d P A 1
H42A H 0.8509 0.6577 0.7087 0.084 Uiso 0.56 1 calc PR A 1
C43A C 0.7795(9) 0.4430(8) 0.7121(3) 0.074(2) Uiso 0.56 1 d P A 1
H43A H 0.6734 0.4214 0.6930 0.088 Uiso 0.56 1 calc PR A 1
C38A C 0.9762(7) 0.3601(7) 0.7562(2) 0.0554(12) Uiso 0.56 1 d P A 1
H38A H 1.0058 0.2796 0.7672 0.066 Uiso 0.56 1 calc PR A 1
C40A C 1.2502(7) 0.5442(6) 0.7971(2) 0.0777(14) Uiso 0.56 1 d P A 1
H40A H 1.3247 0.6499 0.7913 0.117 Uiso 0.56 1 calc PR A 1
H40B H 1.2991 0.4757 0.7830 0.117 Uiso 0.56 1 calc PR A 1
H40C H 1.2362 0.5323 0.8376 0.117 Uiso 0.56 1 calc PR A 1
C48B C 1.1862(12) 0.7262(10) 0.7769(4) 0.108(3) Uiso 0.44 1 d P B 2
H48A H 1.2271 0.7789 0.7427 0.162 Uiso 0.44 1 calc PR B 2
H48B H 1.2798 0.7203 0.7998 0.162 Uiso 0.44 1 calc PR B 2
H48C H 1.1358 0.7827 0.7987 0.162 Uiso 0.44 1 calc PR B 2
C46B C 1.0853(14) 0.4427(12) 0.7684(4) 0.098(3) Uiso 0.44 1 d P B 2
H46B H 1.1918 0.4463 0.7812 0.117 Uiso 0.44 1 calc PR B 2
C47B C 1.0571(8) 0.5680(9) 0.7606(3) 0.0607(14) Uiso 0.44 1 d P B 2
C45B C 0.9449(14) 0.3067(12) 0.7561(5) 0.099(3) Uiso 0.44 1 d P B 2
H45B H 0.9553 0.2171 0.7677 0.118 Uiso 0.44 1 calc PR B 2
C50B C 0.7746(10) 0.4039(10) 0.7213(3) 0.064(2) Uiso 0.44 1 d P B 2
H50B H 0.6684 0.3877 0.7033 0.076 Uiso 0.44 1 calc PR B 2
C49B C 0.9097(12) 0.5593(10) 0.7384(4) 0.081(2) Uiso 0.44 1 d P B 2
H49B H 0.8906 0.6488 0.7334 0.097 Uiso 0.44 1 calc PR B 2
N44B N 0.8209(8) 0.2893(7) 0.7343(3) 0.0632(19) Uiso 0.44 1 d P B 2
H44B H 0.7488 0.1951 0.7249 0.076 Uiso 0.44 1 calc PR B 2
H2 H 0.6321 0.8385 0.7813 0.051(7) Uiso 1 1 d R . .
H1 H 0.3822 1.1467 0.7132 0.054(7) Uiso 1 1 d R . .


_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 1.6409(14) . ?
Si1 C7 1.8680(16) . ?
Si1 C13 1.8722(18) . ?
Si1 C1 1.8721(19) . ?
Si2 O2 1.6385(14) . ?
Si2 C25 1.8667(16) . ?
Si2 C19 1.8714(18) . ?
Si2 C31 1.877(2) . ?
O1 H1 0.8004 . ?
O2 H2 0.8259 . ?
C7 C8 1.392(2) . ?
C7 C12 1.402(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.402(3) . ?
C13 C18 1.399(2) . ?
C13 C14 1.407(2) . ?
C25 C30 1.390(2) . ?
C25 C26 1.400(3) . ?
C31 C32 1.391(3) . ?
C31 C36 1.400(3) . ?
C19 C20 1.399(2) . ?
C19 C24 1.405(2) . ?
C6 C5 1.392(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C32 C33 1.394(3) . ?
C32 H32 0.9500 . ?
C12 C11 1.388(2) . ?
C12 H12 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C23 C22 1.385(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C27 C28 1.381(3) . ?
C27 C26 1.385(2) . ?
C27 H27 0.9500 . ?
C18 C17 1.392(3) . ?
C18 H18 0.9500 . ?
C24 H24 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C28 C29 1.375(3) . ?
C28 H28 0.9500 . ?
C30 C29 1.398(2) . ?
C30 H30 0.9500 . ?
C5 C4 1.381(3) . ?
C5 H5 0.9500 . ?
C22 C21 1.381(3) . ?
C22 H22 0.9500 . ?
C17 H17 0.9500 . ?
C11 C10 1.375(3) . ?
C11 H11 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C33 C34 1.379(3) . ?
C33 H33 0.9500 . ?
C29 H29 0.9500 . ?
C21 C20 1.389(3) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?
C26 H26 0.9500 . ?
C34 C35 1.380(3) . ?
C34 H34 0.9500 . ?
C4 C3 1.375(3) . ?
C4 H4 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H7 0.9500 . ?
C36 C35 1.387(3) . ?
C36 H36 0.9500 . ?
C35 H35 0.9500 . ?
C3 H3 0.9500 . ?
N37A C43A 1.346(8) . ?
N37A C38A 1.420(8) . ?
N37A H37A 0.8800 . ?
C39A C38A 1.347(8) . ?
C39A C41A 1.377(6) . ?
C39A C40A 1.467(7) . ?
C41A C42A 1.400(8) . ?
C41A H41A 0.9500 . ?
C42A C43A 1.255(9) . ?
C42A H42A 0.9500 . ?
C43A H43A 0.9500 . ?
C38A H38A 0.9500 . ?
C40A H40A 0.9800 . ?
C40A H40B 0.9800 . ?
C40A H40C 0.9800 . ?
C48B C47B 1.501(11) . ?
C48B H48A 0.9800 . ?
C48B H48B 0.9800 . ?
C48B H48C 0.9800 . ?
C46B C47B 1.341(11) . ?
C46B C45B 1.391(14) . ?
C46B H46B 0.9500 . ?
C47B C49B 1.335(11) . ?
C45B N44B 1.121(11) . ?
C45B H45B 0.9500 . ?
C50B N44B 1.357(10) . ?
C50B C49B 1.506(12) . ?
C50B H50B 0.9500 . ?
C49B H49B 0.9500 . ?
N44B H44B 0.8800 . ?

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 C7 105.63(8) . . ?
O1 Si1 C13 111.47(8) . . ?
C7 Si1 C13 109.13(8) . . ?
O1 Si1 C1 110.74(8) . . ?
C7 Si1 C1 109.82(8) . . ?
C13 Si1 C1 109.94(8) . . ?
O2 Si2 C25 105.54(8) . . ?
O2 Si2 C19 112.80(8) . . ?
C25 Si2 C19 108.94(8) . . ?
O2 Si2 C31 110.01(8) . . ?
C25 Si2 C31 110.27(8) . . ?
C19 Si2 C31 109.22(8) . . ?
Si1 O1 H1 114.7 . . ?
Si2 O2 H2 115.6 . . ?
C8 C7 C12 117.42(15) . . ?
C8 C7 Si1 122.22(13) . . ?
C12 C7 Si1 120.33(13) . . ?
C6 C1 C2 117.01(17) . . ?
C6 C1 Si1 122.71(13) . . ?
C2 C1 Si1 120.22(14) . . ?
C18 C13 C14 117.09(15) . . ?
C18 C13 Si1 121.81(12) . . ?
C14 C13 Si1 121.10(13) . . ?
C30 C25 C26 117.33(15) . . ?
C30 C25 Si2 122.56(13) . . ?
C26 C25 Si2 120.10(13) . . ?
C32 C31 C36 117.11(17) . . ?
C32 C31 Si2 122.40(14) . . ?
C36 C31 Si2 120.49(15) . . ?
C20 C19 C24 117.32(16) . . ?
C20 C19 Si2 121.67(12) . . ?
C24 C19 Si2 121.00(13) . . ?
C1 C6 C5 121.46(17) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C7 C8 C9 121.24(17) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C15 C14 C13 121.39(16) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C31 C32 C33 121.47(18) . . ?
C31 C32 H32 119.3 . . ?
C33 C32 H32 119.3 . . ?
C11 C12 C7 121.34(18) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C16 C15 C14 120.03(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C22 C23 C24 120.21(17) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C28 C27 C26 119.60(18) . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C17 C18 C13 121.60(15) . . ?
C17 C18 H18 119.2 . . ?
C13 C18 H18 119.2 . . ?
C23 C24 C19 121.14(17) . . ?
C23 C24 H24 119.4 . . ?
C19 C24 H24 119.4 . . ?
C17 C16 C15 119.89(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C29 C28 C27 120.14(17) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C25 C30 C29 121.12(18) . . ?
C25 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C4 C5 C6 120.12(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C21 C22 C23 119.82(18) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C16 C17 C18 119.99(17) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C10 C11 C12 119.94(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C9 C8 119.82(18) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.23(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C34 C33 C32 120.1(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C28 C29 C30 120.04(18) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C22 C21 C20 120.03(18) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C20 C19 121.48(16) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C27 C26 C25 121.76(18) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C33 C34 C35 119.7(2) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C3 C4 C5 119.81(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C3 C2 C1 121.61(19) . . ?
C3 C2 H7 119.2 . . ?
C1 C2 H7 119.2 . . ?
C35 C36 C31 121.6(2) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?
C34 C35 C36 120.0(2) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C43A N37A C38A 118.5(5) . . ?
C43A N37A H37A 120.7 . . ?
C38A N37A H37A 120.7 . . ?
C38A C39A C41A 118.6(4) . . ?
C38A C39A C40A 121.0(5) . . ?
C41A C39A C40A 120.3(4) . . ?
C39A C41A C42A 118.6(4) . . ?
C39A C41A H41A 120.7 . . ?
C42A C41A H41A 120.7 . . ?
C43A C42A C41A 122.4(6) . . ?
C43A C42A H42A 118.8 . . ?
C41A C42A H42A 118.8 . . ?
C42A C43A N37A 121.9(7) . . ?
C42A C43A H43A 119.1 . . ?
N37A C43A H43A 119.1 . . ?
C39A C38A N37A 119.9(5) . . ?
C39A C38A H38A 120.0 . . ?
N37A C38A H38A 120.0 . . ?
C47B C48B H48A 109.5 . . ?
C47B C48B H48B 109.5 . . ?
H48A C48B H48B 109.5 . . ?
C47B C48B H48C 109.5 . . ?
H48A C48B H48C 109.5 . . ?
H48B C48B H48C 109.5 . . ?
C47B C46B C45B 114.0(10) . . ?
C47B C46B H46B 123.0 . . ?
C45B C46B H46B 123.0 . . ?
C49B C47B C46B 121.6(8) . . ?
C49B C47B C48B 115.6(8) . . ?
C46B C47B C48B 122.8(8) . . ?
N44B C45B C46B 128.3(11) . . ?
N44B C45B H45B 115.8 . . ?
C46B C45B H45B 115.8 . . ?
N44B C50B C49B 112.6(8) . . ?
N44B C50B H50B 123.7 . . ?
C49B C50B H50B 123.7 . . ?
C47B C49B C50B 118.3(8) . . ?
C47B C49B H49B 120.9 . . ?
C50B C49B H49B 120.9 . . ?
C45B N44B C50B 124.4(9) . . ?
C45B N44B H44B 117.8 . . ?
C50B N44B H44B 117.8 . . ?

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 Cl1 0.83 2.29 3.1122(15) 173.5 .
O1 H1 Cl1 0.80 2.35 3.1345(16) 166.1 .
N37A H37A Cl1 0.88 2.30 3.129(5) 157.1 1_545
N44B H44B Cl1 0.88 2.11 2.900(6) 148.2 1_545

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1481651'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 O, C6 H8 N, Cl'
_chemical_formula_sum            'C25 H24 Cl N O'
_chemical_formula_weight         389.90

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   P21/C

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                   14.078(3)
_cell_length_b                   9.2242(18)
_cell_length_c                   16.232(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.74(3)
_cell_angle_gamma                90.00
_cell_volume                     2093.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3503
_cell_measurement_theta_min      1.46
_cell_measurement_theta_max      27.54

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'NONIUS KAPPA CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            71176
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4800
_reflns_number_gt                3503
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (2000)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XSEED
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0455P)²+0.7229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    NOREF
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4800
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Cl1 Cl 0.98510(3) 0.61090(4) 0.15371(3) 0.03803(12) Uani 1 1 d . . .
O1 O 0.76783(7) 0.70257(11) 0.13146(6) 0.0284(2) Uani 1 1 d . . .
C3 C 0.70048(10) 0.64053(15) -0.00849(9) 0.0253(3) Uani 1 1 d . . .
C2 C 0.69257(10) 0.62049(15) 0.08481(9) 0.0244(3) Uani 1 1 d . . .
C20 C 0.74722(11) 0.41657(16) 0.18429(9) 0.0300(3) Uani 1 1 d . . .
H20 H 0.7767 0.4869 0.2217 0.036 Uiso 1 1 calc R . .
C16 C 0.65841(11) 0.35503(16) 0.05417(9) 0.0308(3) Uani 1 1 d . . .
H16 H 0.6272 0.3828 0.0015 0.037 Uiso 1 1 calc R . .
C4 C 0.78634(11) 0.60191(17) -0.03780(10) 0.0330(3) Uani 1 1 d . . .
H4 H 0.8372 0.5642 -0.0003 0.040 Uiso 1 1 calc R . .
C14 C 0.53071(10) 0.60642(17) 0.14360(9) 0.0307(3) Uani 1 1 d . . .
H14 H 0.5372 0.5041 0.1483 0.037 Uiso 1 1 calc R . .
C9 C 0.60057(10) 0.68652(16) 0.11096(9) 0.0263(3) Uani 1 1 d . . .
N21 N 0.95221(10) 0.11049(16) 0.16137(9) 0.0404(3) Uani 1 1 d . . .
H21 H 0.9762 0.1168 0.2138 0.049 Uiso 1 1 calc R . .
C7 C 0.64027(12) 0.71143(18) -0.14817(10) 0.0386(4) Uani 1 1 d . . .
H7 H 0.5898 0.7497 -0.1859 0.046 Uiso 1 1 calc R . .
C15 C 0.70084(10) 0.46011(15) 0.10798(9) 0.0252(3) Uani 1 1 d . . .
C5 C 0.79836(12) 0.61781(19) -0.12076(10) 0.0392(4) Uani 1 1 d . . .
H5 H 0.8570 0.5898 -0.1397 0.047 Uiso 1 1 calc R . .
C12 C 0.44088(11) 0.82235(19) 0.16360(10) 0.0383(4) Uani 1 1 d . . .
H12 H 0.3871 0.8687 0.1823 0.046 Uiso 1 1 calc R . .
C11 C 0.50936(12) 0.90326(18) 0.13028(11) 0.0398(4) Uani 1 1 d . . .
H11 H 0.5023 1.0054 0.1253 0.048 Uiso 1 1 calc R . .
C24 C 0.87835(12) 0.0905(2) -0.00117(11) 0.0431(4) Uani 1 1 d . . .
C6 C 0.72578(13) 0.67401(19) -0.17612(10) 0.0395(4) Uani 1 1 d . . .
H6 H 0.7346 0.6868 -0.2328 0.047 Uiso 1 1 calc R . .
C19 C 0.75075(11) 0.27163(17) 0.20628(10) 0.0340(4) Uani 1 1 d . . .
H19 H 0.7832 0.2431 0.2584 0.041 Uiso 1 1 calc R . .
C8 C 0.62735(11) 0.69355(17) -0.06500(9) 0.0319(3) Uani 1 1 d . . .
H2 H 0.5677 0.7180 -0.0468 0.038 Uiso 1 1 calc R . .
C17 C 0.66137(11) 0.21061(17) 0.07685(10) 0.0349(4) Uani 1 1 d . . .
H17 H 0.6316 0.1399 0.0399 0.042 Uiso 1 1 calc R . .
C22 C 0.91975(13) -0.01663(18) 0.13157(11) 0.0419(4) Uani 1 1 d . . .
H22 H 0.9226 -0.0992 0.1668 0.050 Uiso 1 1 calc R . .
C13 C 0.45083(11) 0.67413(19) 0.16970(10) 0.0363(4) Uani 1 1 d . . .
H13 H 0.4032 0.6179 0.1917 0.044 Uiso 1 1 calc R . .
C10 C 0.58832(11) 0.83588(17) 0.10403(10) 0.0340(4) Uani 1 1 d . . .
H10 H 0.6349 0.8925 0.0809 0.041 Uiso 1 1 calc R . .
C23 C 0.88231(12) -0.02870(19) 0.05026(11) 0.0427(4) Uani 1 1 d . . .
H23 H 0.8589 -0.1196 0.0291 0.051 Uiso 1 1 calc R . .
C26 C 0.94935(13) 0.22872(19) 0.11387(13) 0.0459(5) Uani 1 1 d . . .
H26 H 0.9721 0.3187 0.1369 0.055 Uiso 1 1 calc R . .
C18 C 0.70747(11) 0.16832(17) 0.15314(10) 0.0349(4) Uani 1 1 d . . .
H18 H 0.7092 0.0690 0.1687 0.042 Uiso 1 1 calc R . .
C25 C 0.91374(13) 0.2202(2) 0.03239(13) 0.0479(5) Uani 1 1 d . . .
H25 H 0.9132 0.3040 -0.0017 0.057 Uiso 1 1 calc R . .
C27 C 0.83486(17) 0.0805(3) -0.08985(13) 0.0758(7) Uani 1 1 d . . .
H27A H 0.8275 -0.0216 -0.1059 0.114 Uiso 1 1 calc R . .
H27B H 0.8766 0.1290 -0.1255 0.114 Uiso 1 1 calc R . .
H27C H 0.7720 0.1276 -0.0960 0.114 Uiso 1 1 calc R . .
H1 H 0.8271 0.6509 0.1354 0.074(7) Uiso 1 1 d R . .


_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
O1 C2 1.4426(17) . ?
O1 H1 0.9566 . ?
C3 C8 1.385(2) . ?
C3 C4 1.396(2) . ?
C3 C2 1.543(2) . ?
C2 C15 1.528(2) . ?
C2 C9 1.535(2) . ?
C20 C19 1.383(2) . ?
C20 C15 1.390(2) . ?
C20 H20 0.9500 . ?
C16 C17 1.381(2) . ?
C16 C15 1.392(2) . ?
C16 H16 0.9500 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C14 C9 1.384(2) . ?
C14 C13 1.395(2) . ?
C14 H14 0.9500 . ?
C9 C10 1.391(2) . ?
N21 C22 1.329(2) . ?
N21 C26 1.334(2) . ?
N21 H21 0.8800 . ?
C7 C6 1.379(2) . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C12 C13 1.377(2) . ?
C12 C11 1.379(2) . ?
C12 H12 0.9500 . ?
C11 C10 1.384(2) . ?
C11 H11 0.9500 . ?
C24 C23 1.378(2) . ?
C24 C25 1.383(3) . ?
C24 C27 1.500(3) . ?
C6 H6 0.9500 . ?
C19 C18 1.378(2) . ?
C19 H19 0.9500 . ?
C8 H2 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C22 C23 1.367(2) . ?
C22 H22 0.9500 . ?
C13 H13 0.9500 . ?
C10 H10 0.9500 . ?
C23 H23 0.9500 . ?
C26 C25 1.361(3) . ?
C26 H26 0.9500 . ?
C18 H18 0.9500 . ?
C25 H25 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C2 O1 H1 110.8 . . ?
C8 C3 C4 118.06(14) . . ?
C8 C3 C2 123.97(13) . . ?
C4 C3 C2 117.98(13) . . ?
O1 C2 C15 110.42(11) . . ?
O1 C2 C9 103.78(11) . . ?
C15 C2 C9 111.01(12) . . ?
O1 C2 C3 108.62(11) . . ?
C15 C2 C3 110.22(11) . . ?
C9 C2 C3 112.60(12) . . ?
C19 C20 C15 120.53(14) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C17 C16 C15 120.47(14) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C5 C4 C3 120.92(15) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C9 C14 C13 120.76(15) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C9 C10 118.20(14) . . ?
C14 C9 C2 123.66(13) . . ?
C10 C9 C2 118.10(13) . . ?
C22 N21 C26 121.69(16) . . ?
C22 N21 H21 119.2 . . ?
C26 N21 H21 119.2 . . ?
C6 C7 C8 120.49(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C20 C15 C16 118.70(14) . . ?
C20 C15 C2 120.90(13) . . ?
C16 C15 C2 120.34(13) . . ?
C6 C5 C4 120.50(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C13 C12 C11 119.72(15) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C11 C10 120.11(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C23 C24 C25 117.70(17) . . ?
C23 C24 C27 121.02(19) . . ?
C25 C24 C27 121.26(19) . . ?
C7 C6 C5 119.20(15) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C18 C19 C20 120.47(15) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C3 C8 C7 120.80(15) . . ?
C3 C8 H2 119.6 . . ?
C7 C8 H2 119.6 . . ?
C16 C17 C18 120.41(15) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
N21 C22 C23 120.04(16) . . ?
N21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C12 C13 C14 120.11(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C11 C10 C9 121.08(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C22 C23 C24 120.23(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
N21 C26 C25 119.86(16) . . ?
N21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C19 C18 C17 119.41(15) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C26 C25 C24 120.48(17) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

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
N21 H21 Cl1 0.88 2.16 3.0277(17) 170.5 2_745
O1 H1 Cl1 0.96 2.24 3.1531(12) 159.4 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.060
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_7
_database_code_depnum_ccdc_archive 'CCDC 1481652'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'0.271(C18 H16 O Si), 0.729(C19 H16 O), C6 H8 N, Cl'
_chemical_formula_sum            'C24.73 H24 Cl N O Si0.27'
_chemical_formula_weight         394.24

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'
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'
O O 0.0106 0.0060 '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

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

_cell_length_a                   8.8493(18)
_cell_length_b                   9.1507(18)
_cell_length_c                   14.380(3)
_cell_angle_alpha                91.40(3)
_cell_angle_beta                 99.68(3)
_cell_angle_gamma                115.03(3)
_cell_volume                     1034.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3890
_cell_measurement_theta_min      1.44
_cell_measurement_theta_max      27.55

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 apex II DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14134
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.55
_reflns_number_total             4771
_reflns_number_gt                3890
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0652P)²+0.8661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4771
_refine_ls_number_parameters     218
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1435
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.72068(7) 0.71285(7) 0.49058(4) 0.03547(15) Uani 1 1 d . . .
Si1 Si 0.6710(4) 0.7825(4) 0.7612(3) 0.0263(16) Uani 0.271(3) 1 d PD A 2
O1 O 0.5735(12) 0.7730(12) 0.6529(4) 0.0203(19) Uiso 0.271(3) 1 d PD A 2
H1 H 0.5939 0.7129 0.6168 0.024 Uiso 0.271(3) 1 calc PR A 2
N1 N 0.7433(2) 0.3899(2) 0.47061(14) 0.0358(4) Uani 1 1 d . . .
H1A H 0.7275 0.4786 0.4714 0.043 Uiso 1 1 calc R . .
C1 C 0.7142(12) 0.6023(8) 0.7840(10) 0.038 Uiso 0.271(3) 1 d PD A 2
C2 C 0.8663(13) 0.6127(12) 0.8379(11) 0.038 Uiso 0.271(3) 1 d PD A 2
H2 H 0.9581 0.7114 0.8675 0.046 Uiso 0.271(3) 1 calc PR A 2
C3 C 0.8672(14) 0.4604(9) 0.8429(10) 0.038 Uiso 0.271(3) 1 d PD A 2
H3 H 0.9665 0.4536 0.8754 0.046 Uiso 0.271(3) 1 calc PR A 2
C4 C 0.7250(10) 0.3181(12) 0.8013(9) 0.038 Uiso 0.271(3) 1 d PD A 2
H4 H 0.7274 0.2158 0.8069 0.046 Uiso 0.271(3) 1 calc PR A 2
C5 C 0.5794(13) 0.3266(14) 0.7513(10) 0.038 Uiso 0.271(3) 1 d PD A 2
H5 H 0.4836 0.2276 0.7259 0.046 Uiso 0.271(3) 1 calc PR A 2
C6 C 0.5657(14) 0.4714(11) 0.7361(11) 0.038 Uiso 0.271(3) 1 d PD A 2
H6 H 0.4705 0.4796 0.6992 0.046 Uiso 0.271(3) 1 calc PR A 2
C7 C 0.5293(13) 0.7861(13) 0.8432(6) 0.038 Uiso 0.271(3) 1 d PD A 2
C8 C 0.4408(12) 0.8813(13) 0.8250(7) 0.038 Uiso 0.271(3) 1 d PD A 2
H8 H 0.4515 0.9442 0.7728 0.046 Uiso 0.271(3) 1 calc PR A 2
C9 C 0.3356(12) 0.8783(12) 0.8883(6) 0.038 Uiso 0.271(3) 1 d PD A 2
H9 H 0.2745 0.9424 0.8793 0.046 Uiso 0.271(3) 1 calc PR A 2
C10 C 0.3177(13) 0.7836(12) 0.9643(7) 0.038 Uiso 0.271(3) 1 d PD A 2
H10 H 0.2506 0.7883 1.0083 0.046 Uiso 0.271(3) 1 calc PR A 2
C11 C 0.3998(14) 0.6818(12) 0.9747(9) 0.038 Uiso 0.271(3) 1 d PD A 2
H11 H 0.3773 0.6080 1.0215 0.046 Uiso 0.271(3) 1 calc PR A 2
C12 C 0.515(3) 0.687(2) 0.9172(12) 0.038 Uiso 0.271(3) 1 d PD A 2
H12 H 0.5795 0.6270 0.9279 0.046 Uiso 0.271(3) 1 calc PR A 2
C20 C 0.8270(3) 0.3669(3) 0.40647(17) 0.0358(5) Uani 1 1 d . . .
C13 C 0.8797(8) 0.9661(9) 0.7935(6) 0.038 Uiso 0.271(3) 1 d PD A 2
C14 C 0.9729(11) 1.0169(13) 0.7214(7) 0.038 Uiso 0.271(3) 1 d PD A 2
H14 H 0.9317 0.9610 0.6593 0.046 Uiso 0.271(3) 1 calc PR A 2
C15 C 1.1297(11) 1.1538(12) 0.7450(7) 0.038 Uiso 0.271(3) 1 d PD A 2
H15 H 1.1959 1.1888 0.6973 0.046 Uiso 0.271(3) 1 calc PR A 2
C16 C 1.1945(11) 1.2421(13) 0.8348(6) 0.038 Uiso 0.271(3) 1 d PD A 2
H16 H 1.3022 1.3336 0.8494 0.046 Uiso 0.271(3) 1 calc PR A 2
C17 C 1.0906(12) 1.1868(13) 0.9019(8) 0.038 Uiso 0.271(3) 1 d PD A 2
H17 H 1.1286 1.2466 0.9628 0.046 Uiso 0.271(3) 1 calc PR A 2
C18 C 0.9343(13) 1.0488(13) 0.8848(6) 0.038 Uiso 0.271(3) 1 d PD A 2
H18 H 0.8687 1.0133 0.9327 0.046 Uiso 0.271(3) 1 calc PR A 2
C22 C 0.7985(4) 0.1228(3) 0.4725(2) 0.0599(8) Uani 1 1 d . . .
H22 H 0.8203 0.0296 0.4735 0.072 Uiso 1 1 calc R . .
C19 C 0.8793(4) 0.4877(3) 0.3379(2) 0.0512(7) Uani 1 1 d . . .
H19A H 0.9011 0.5944 0.3672 0.077 Uiso 1 1 calc R . .
H19B H 0.7883 0.4559 0.2815 0.077 Uiso 1 1 calc R . .
H19C H 0.9831 0.4931 0.3195 0.077 Uiso 1 1 calc R . .
C21 C 0.8549(3) 0.2296(3) 0.4085(2) 0.0504(7) Uani 1 1 d . . .
H21 H 0.9146 0.2096 0.3644 0.060 Uiso 1 1 calc R . .
C24 C 0.6825(3) 0.2856(4) 0.5334(2) 0.0498(7) Uani 1 1 d . . .
H24 H 0.6207 0.3060 0.5760 0.060 Uiso 1 1 calc R . .
C23 C 0.7100(4) 0.1486(4) 0.5359(2) 0.0600(8) Uani 1 1 d . . .
H23 H 0.6688 0.0736 0.5804 0.072 Uiso 1 1 calc R . .
C13B C 0.8432(3) 0.9338(3) 0.7901(2) 0.0232(6) Uiso 0.729(3) 1 d PD A 1
C14B C 0.9413(5) 0.9918(5) 0.7210(3) 0.038 Uiso 0.729(3) 1 d P A 1
H14B H 0.9015 0.9339 0.6594 0.046 Uiso 0.729(3) 1 calc PR A 1
C15B C 1.0935(5) 1.1297(5) 0.7383(3) 0.038 Uiso 0.729(3) 1 d P A 1
H15B H 1.1569 1.1654 0.6895 0.046 Uiso 0.729(3) 1 calc PR A 1
C16B C 1.1533(5) 1.2159(5) 0.8281(3) 0.038 Uiso 0.729(3) 1 d P A 1
H16B H 1.2573 1.3118 0.8406 0.046 Uiso 0.729(3) 1 calc PR A 1
C17B C 1.0611(5) 1.1619(5) 0.8989(3) 0.038 Uiso 0.729(3) 1 d P A 1
H17B H 1.1023 1.2196 0.9606 0.046 Uiso 0.729(3) 1 calc PR A 1
C18B C 0.9086(6) 1.0234(5) 0.8796(3) 0.038 Uiso 0.729(3) 1 d P A 1
H18B H 0.8460 0.9879 0.9287 0.046 Uiso 0.729(3) 1 calc PR A 1
C25 C 0.6775(3) 0.7770(3) 0.7704(2) 0.0148(17) Uani 0.729(3) 1 d PD A 1
O1B O 0.5876(4) 0.7668(5) 0.6753(2) 0.0312(6) Uani 0.729(3) 1 d PD A 1
H1B H 0.6482 0.7656 0.6364 0.037 Uiso 0.729(3) 1 calc PR A 1
C1B C 0.7081(6) 0.6250(4) 0.7806(4) 0.038 Uiso 0.729(3) 1 d PD A 1
C2B C 0.8573(6) 0.6289(5) 0.8323(4) 0.038 Uiso 0.729(3) 1 d P A 1
H2B H 0.9468 0.7317 0.8579 0.046 Uiso 0.729(3) 1 calc PR A 1
C3B C 0.8842(6) 0.4916(4) 0.8489(4) 0.038 Uiso 0.729(3) 1 d P A 1
H3B H 0.9887 0.5022 0.8858 0.046 Uiso 0.729(3) 1 calc PR A 1
C4B C 0.7580(5) 0.3393(5) 0.8113(3) 0.038 Uiso 0.729(3) 1 d P A 1
H4B H 0.7757 0.2451 0.8216 0.046 Uiso 0.729(3) 1 calc PR A 1
C5B C 0.6060(5) 0.3264(6) 0.7587(4) 0.038 Uiso 0.729(3) 1 d P A 1
H5B H 0.5180 0.2232 0.7323 0.046 Uiso 0.729(3) 1 calc PR A 1
C6B C 0.5840(6) 0.4659(5) 0.7450(4) 0.038 Uiso 0.729(3) 1 d P A 1
H6B H 0.4782 0.4542 0.7093 0.046 Uiso 0.729(3) 1 calc PR A 1
C7B C 0.5533(4) 0.7826(4) 0.8314(2) 0.0249(6) Uiso 0.729(3) 1 d PD A 1
C8B C 0.4671(5) 0.8781(5) 0.8105(3) 0.038 Uiso 0.729(3) 1 d P A 1
H8B H 0.4849 0.9374 0.7569 0.046 Uiso 0.729(3) 1 calc PR A 1
C9B C 0.3562(5) 0.8906(5) 0.8646(3) 0.038 Uiso 0.729(3) 1 d P A 1
H9B H 0.2993 0.9567 0.8476 0.046 Uiso 0.729(3) 1 calc PR A 1
C10B C 0.3289(5) 0.8061(5) 0.9435(3) 0.038 Uiso 0.729(3) 1 d P A 1
H10B H 0.2517 0.8123 0.9803 0.046 Uiso 0.729(3) 1 calc PR A 1
C11B C 0.4145(6) 0.7132(5) 0.9681(3) 0.038 Uiso 0.729(3) 1 d P A 1
H11B H 0.4001 0.6584 1.0235 0.046 Uiso 0.729(3) 1 calc PR A 1
C12B C 0.5223(10) 0.6994(9) 0.9117(5) 0.038 Uiso 0.729(3) 1 d P A 1
H12B H 0.5767 0.6312 0.9283 0.046 Uiso 0.729(3) 1 calc PR A 1


_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 1.6295(11) . ?
Si1 C1 1.8684(11) . ?
Si1 C13 1.8699(14) . ?
Si1 C7 1.8700(11) . ?
O1 H1 0.8400 . ?
N1 C24 1.337(3) . ?
N1 C20 1.340(3) . ?
N1 H1A 0.8800 . ?
C1 C6 1.3992(13) . ?
C1 C2 1.3994(11) . ?
C2 C3 1.4001(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3999(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3999(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3996(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.3996(11) . ?
C7 C8 1.3997(11) . ?
C8 C9 1.4000(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3997(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.3997(11) . ?
C10 H10 0.9500 . ?
C11 C12 1.3998(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C20 C21 1.379(3) . ?
C20 C19 1.478(4) . ?
C13 C14 1.3995(11) . ?
C13 C18 1.3996(12) . ?
C14 C15 1.3999(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.3995(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.3995(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.4000(12) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C22 C21 1.355(4) . ?
C22 C23 1.374(5) . ?
C22 H22 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 H21 0.9500 . ?
C24 C23 1.375(4) . ?
C24 H24 0.9500 . ?
C23 H23 0.9500 . ?
C13B C14B 1.397(4) . ?
C13B C18B 1.399(4) . ?
C13B C25 1.5327(13) . ?
C14B C15B 1.379(5) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.391(5) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.382(5) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.384(5) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C25 O1B 1.4418(11) . ?
C25 C1B 1.5313(11) . ?
C25 C7B 1.5324(11) . ?
O1B H1B 0.8400 . ?
C1B C2B 1.388(5) . ?
C1B C6B 1.417(5) . ?
C2B C3B 1.393(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.387(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.384(5) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.385(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.392(4) . ?
C7B C12B 1.400(4) . ?
C8B C9B 1.389(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.386(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.375(5) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.394(5) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?

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 C1 113.2(6) . . ?
O1 Si1 C13 112.5(5) . . ?
C1 Si1 C13 107.0(5) . . ?
O1 Si1 C7 108.1(5) . . ?
C1 Si1 C7 106.4(6) . . ?
C13 Si1 C7 109.4(5) . . ?
Si1 O1 H1 109.5 . . ?
C24 N1 C20 123.6(2) . . ?
C24 N1 H1A 118.2 . . ?
C20 N1 H1A 118.2 . . ?
C6 C1 C2 132.8(6) . . ?
C6 C1 Si1 103.8(6) . . ?
C2 C1 Si1 123.5(6) . . ?
C1 C2 C3 112.1(9) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 H2 124.0 . . ?
C4 C3 C2 121.4(11) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.0(11) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 124.3(11) . . ?
C6 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C1 C6 C5 109.3(8) . . ?
C1 C6 H6 125.3 . . ?
C5 C6 H6 125.3 . . ?
C12 C7 C8 124.4(7) . . ?
C12 C7 Si1 117.0(6) . . ?
C8 C7 Si1 118.6(5) . . ?
C7 C8 C9 116.1(7) . . ?
C7 C8 H8 122.0 . . ?
C9 C8 H8 122.0 . . ?
C10 C9 C8 122.0(8) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 119.3(8) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.9(10) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C7 C12 C11 117.0(9) . . ?
C7 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
N1 C20 C21 117.2(2) . . ?
N1 C20 C19 117.9(2) . . ?
C21 C20 C19 124.9(2) . . ?
C14 C13 C18 122.9(6) . . ?
C14 C13 Si1 116.5(5) . . ?
C18 C13 Si1 120.6(5) . . ?
C13 C14 C15 117.0(8) . . ?
C13 C14 H14 121.5 . . ?
C15 C14 H14 121.5 . . ?
C16 C15 C14 123.7(9) . . ?
C16 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
C17 C16 C15 115.7(9) . . ?
C17 C16 H16 122.1 . . ?
C15 C16 H16 122.1 . . ?
C16 C17 C18 124.2(10) . . ?
C16 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C13 C18 C17 116.5(8) . . ?
C13 C18 H18 121.8 . . ?
C17 C18 H18 121.8 . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
N1 C24 C23 119.5(3) . . ?
N1 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C22 C23 C24 118.5(3) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
C14B C13B C18B 116.1(3) . . ?
C14B C13B C25 121.9(3) . . ?
C18B C13B C25 121.9(3) . . ?
C15B C14B C13B 122.7(4) . . ?
C15B C14B H14B 118.6 . . ?
C13B C14B H14B 118.6 . . ?
C14B C15B C16B 119.3(4) . . ?
C14B C15B H15B 120.3 . . ?
C16B C15B H15B 120.3 . . ?
C17B C16B C15B 119.9(4) . . ?
C17B C16B H16B 120.1 . . ?
C15B C16B H16B 120.1 . . ?
C16B C17B C18B 119.6(4) . . ?
C16B C17B H17B 120.2 . . ?
C18B C17B H17B 120.2 . . ?
C17B C18B C13B 122.3(4) . . ?
C17B C18B H18B 118.8 . . ?
C13B C18B H18B 118.8 . . ?
O1B C25 C1B 108.7(3) . . ?
O1B C25 C7B 102.8(3) . . ?
C1B C25 C7B 111.9(3) . . ?
O1B C25 C13B 109.1(3) . . ?
C1B C25 C13B 112.6(3) . . ?
C7B C25 C13B 111.2(3) . . ?
C2B C1B C6B 113.2(3) . . ?
C2B C1B C25 122.7(3) . . ?
C6B C1B C25 123.9(3) . . ?
C1B C2B C3B 124.1(4) . . ?
C1B C2B H2B 117.9 . . ?
C3B C2B H2B 117.9 . . ?
C4B C3B C2B 119.8(5) . . ?
C4B C3B H3B 120.1 . . ?
C2B C3B H3B 120.1 . . ?
C3B C4B C5B 119.2(4) . . ?
C3B C4B H4B 120.4 . . ?
C5B C4B H4B 120.4 . . ?
C6B C5B C4B 119.1(4) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
C5B C6B C1B 124.6(4) . . ?
C5B C6B H6B 117.7 . . ?
C1B C6B H6B 117.7 . . ?
C8B C7B C12B 115.6(3) . . ?
C8B C7B C25 120.5(3) . . ?
C12B C7B C25 123.9(3) . . ?
C7B C8B C9B 122.9(3) . . ?
C7B C8B H8B 118.6 . . ?
C9B C8B H8B 118.6 . . ?
C8B C9B C10B 119.7(4) . . ?
C8B C9B H9B 120.2 . . ?
C10B C9B H9B 120.2 . . ?
C11B C10B C9B 119.5(3) . . ?
C11B C10B H10B 120.3 . . ?
C9B C10B H10B 120.3 . . ?
C10B C11B C12B 119.9(4) . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C11B C12B C7B 122.4(4) . . ?
C11B C12B H12B 118.8 . . ?
C7B C12B H12B 118.8 . . ?

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 Cl1 0.84 2.29 3.002(9) 143.0 .
N1 H1A Cl1 0.88 2.18 3.055(2) 171.6 .
O1B H1B Cl1 0.84 2.39 3.188(4) 159.2 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.055
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_8
_database_code_depnum_ccdc_archive 'CCDC 1481653'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'0.244(C18 H16 O Si), 0.756(C19 H16 O), C6 H8 N, Cl '
_chemical_formula_sum            'C24.76 H24 Cl N O Si0.24'
_chemical_formula_weight         393.76

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

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

_cell_length_a                   8.8549(18)
_cell_length_b                   9.1480(18)
_cell_length_c                   14.370(3)
_cell_angle_alpha                91.44(3)
_cell_angle_beta                 99.75(3)
_cell_angle_gamma                115.05(3)
_cell_volume                     1033.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3795
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.96

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 APEX II DUO'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21550
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.96
_reflns_number_total             4954
_reflns_number_gt                3795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0563P)²+1.0858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    NOREF
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4954
_refine_ls_number_parameters     215
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1585
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.22100(8) 0.21123(7) 0.49079(4) 0.03518(16) Uani 1 1 d . . .
C1 C 0.1772(4) 0.2773(4) 0.7708(2) 0.0173(19) Uani 0.756(3) 1 d PD A 1
O1 O 0.0886(5) 0.2666(5) 0.6750(2) 0.0323(7) Uani 0.756(3) 1 d PD A 1
N25 N 0.2430(3) 0.8889(2) 0.47061(15) 0.0341(5) Uani 1 1 d . . .
H25 H 0.2272 0.9776 0.4712 0.041 Uiso 1 1 calc R . .
C2 C 0.3432(5) 0.4338(5) 0.7903(3) 0.037 Uiso 0.756(3) 1 d PD A 1
C8 C 0.2075(6) 0.1250(4) 0.7803(4) 0.037 Uiso 0.756(3) 1 d PD A 1
C14 C 0.0530(6) 0.2829(6) 0.8315(3) 0.037 Uiso 0.756(3) 1 d PD A 1
C23 C 0.3267(3) 0.8653(3) 0.40670(18) 0.0332(5) Uani 1 1 d . . .
C15 C 0.0225(8) 0.2001(9) 0.9114(5) 0.037 Uiso 0.756(3) 1 d P A 1
H15 H 0.0768 0.1316 0.9276 0.044 Uiso 0.756(3) 1 calc PR A 1
C3 C 0.4405(5) 0.4917(5) 0.7203(3) 0.037 Uiso 0.756(3) 1 d P A 1
H3 H 0.4002 0.4341 0.6585 0.044 Uiso 0.756(3) 1 calc PR A 1
C9 C 0.3576(6) 0.1296(5) 0.8323(4) 0.037 Uiso 0.756(3) 1 d P A 1
H9 H 0.4471 0.2324 0.8582 0.044 Uiso 0.756(3) 1 calc PR A 1
C7 C 0.4089(5) 0.5229(5) 0.8801(3) 0.037 Uiso 0.756(3) 1 d P A 1
H7 H 0.3474 0.4863 0.9296 0.044 Uiso 0.756(3) 1 calc PR A 1
C6 C 0.5609(5) 0.6629(5) 0.8992(3) 0.037 Uiso 0.756(3) 1 d P A 1
H6 H 0.6012 0.7219 0.9606 0.044 Uiso 0.756(3) 1 calc PR A 1
C5 C 0.6535(5) 0.7159(5) 0.8284(3) 0.037 Uiso 0.756(3) 1 d P A 1
H5 H 0.7584 0.8110 0.8412 0.044 Uiso 0.756(3) 1 calc PR A 1
C10 C 0.3837(6) -0.0084(4) 0.8484(4) 0.037 Uiso 0.756(3) 1 d P A 1
H10 H 0.4883 0.0019 0.8851 0.044 Uiso 0.756(3) 1 calc PR A 1
C19 C -0.0337(5) 0.3785(5) 0.8100(3) 0.037 Uiso 0.756(3) 1 d P A 1
H19 H -0.0167 0.4373 0.7562 0.044 Uiso 0.756(3) 1 calc PR A 1
C13 C 0.0833(6) -0.0339(5) 0.7452(4) 0.037 Uiso 0.756(3) 1 d P A 1
H13 H -0.0232 -0.0454 0.7106 0.044 Uiso 0.756(3) 1 calc PR A 1
C16 C -0.0848(5) 0.2136(5) 0.9686(4) 0.037 Uiso 0.756(3) 1 d P A 1
H16 H -0.0984 0.1592 1.0242 0.044 Uiso 0.756(3) 1 calc PR A 1
C11 C 0.2573(5) -0.1604(5) 0.8110(3) 0.037 Uiso 0.756(3) 1 d P A 1
H11 H 0.2747 -0.2546 0.8218 0.044 Uiso 0.756(3) 1 calc PR A 1
C4 C 0.5931(5) 0.6300(5) 0.7384(3) 0.037 Uiso 0.756(3) 1 d P A 1
H4 H 0.6563 0.6662 0.6897 0.044 Uiso 0.756(3) 1 calc PR A 1
C18 C -0.1439(5) 0.3905(5) 0.8648(3) 0.037 Uiso 0.756(3) 1 d P A 1
H18 H -0.2010 0.4564 0.8480 0.044 Uiso 0.756(3) 1 calc PR A 1
C22 C 0.3545(4) 0.7280(4) 0.4084(2) 0.0475(7) Uani 1 1 d . . .
H22 H 0.4142 0.7079 0.3644 0.057 Uiso 1 1 calc R . .
C12 C 0.1047(5) -0.1742(6) 0.7574(4) 0.037 Uiso 0.756(3) 1 d P A 1
H12 H 0.0174 -0.2772 0.7298 0.044 Uiso 0.756(3) 1 calc PR A 1
C17 C -0.1705(5) 0.3064(5) 0.9437(3) 0.037 Uiso 0.756(3) 1 d P A 1
H17 H -0.2475 0.3127 0.9806 0.044 Uiso 0.756(3) 1 calc PR A 1
C24 C 0.1822(4) 0.7847(4) 0.5335(2) 0.0482(7) Uani 1 1 d . . .
H24 H 0.1209 0.8056 0.5762 0.058 Uiso 1 1 calc R . .
C21 C 0.2969(4) 0.6205(4) 0.4730(3) 0.0578(9) Uani 1 1 d . . .
H21 H 0.3179 0.5268 0.4742 0.069 Uiso 1 1 calc R . .
C25 C 0.3801(4) 0.9870(4) 0.3383(2) 0.0501(7) Uani 1 1 d . . .
H25A H 0.2889 0.9563 0.2820 0.075 Uiso 1 1 calc R . .
H25B H 0.4831 0.9912 0.3195 0.075 Uiso 1 1 calc R . .
H25C H 0.4036 1.0939 0.3681 0.075 Uiso 1 1 calc R . .
C20 C 0.2088(4) 0.6476(4) 0.5361(3) 0.0576(9) Uani 1 1 d . . .
H20 H 0.1671 0.5728 0.5807 0.069 Uiso 1 1 calc R . .
Si1 Si 0.1699(5) 0.2813(5) 0.7600(4) 0.0227(17) Uani 0.244(3) 1 d PD A 2
O2 O 0.0725(13) 0.2749(13) 0.6520(5) 0.016(2) Uiso 0.244(3) 1 d PD A 2
H2 H 0.1432 0.3028 0.6160 0.019 Uiso 0.244(3) 1 calc PR A 2
C2B C 0.3777(10) 0.4657(12) 0.7932(7) 0.037 Uiso 0.244(3) 1 d PD A 2
C3B C 0.4754(12) 0.5192(14) 0.7232(8) 0.037 Uiso 0.244(3) 1 d PD A 2
H3B H 0.4351 0.4635 0.6610 0.044 Uiso 0.244(3) 1 calc PR A 2
C4B C 0.6328(12) 0.6557(13) 0.7458(8) 0.037 Uiso 0.244(3) 1 d PD A 2
H4B H 0.6990 0.6881 0.6980 0.044 Uiso 0.244(3) 1 calc PR A 2
C5B C 0.6980(13) 0.7469(14) 0.8349(7) 0.037 Uiso 0.244(3) 1 d PD A 2
H5B H 0.8038 0.8409 0.8489 0.044 Uiso 0.244(3) 1 calc PR A 2
C6B C 0.5947(13) 0.6883(15) 0.9019(9) 0.037 Uiso 0.244(3) 1 d PD A 2
H6B H 0.6344 0.7449 0.9639 0.044 Uiso 0.244(3) 1 calc PR A 2
C7B C 0.4369(14) 0.5519(14) 0.8838(8) 0.037 Uiso 0.244(3) 1 d PD A 2
H7B H 0.3716 0.5187 0.9319 0.044 Uiso 0.244(3) 1 calc PR A 2
C8B C 0.2136(14) 0.1018(9) 0.7848(12) 0.037 Uiso 0.244(3) 1 d PD A 2
C9B C 0.3654(15) 0.1090(14) 0.8373(12) 0.037 Uiso 0.244(3) 1 d PD A 2
H9B H 0.4588 0.2073 0.8665 0.044 Uiso 0.244(3) 1 calc PR A 2
C10B C 0.3653(15) -0.0437(10) 0.8423(11) 0.037 Uiso 0.244(3) 1 d PD A 2
H10B H 0.4645 -0.0512 0.8742 0.044 Uiso 0.244(3) 1 calc PR A 2
C11B C 0.2216(11) -0.1855(13) 0.8012(10) 0.037 Uiso 0.244(3) 1 d PD A 2
H11B H 0.2223 -0.2888 0.8043 0.044 Uiso 0.244(3) 1 calc PR A 2
C12B C 0.0770(15) -0.1706(16) 0.7553(12) 0.037 Uiso 0.244(3) 1 d PD A 2
H12B H -0.0233 -0.2687 0.7354 0.044 Uiso 0.244(3) 1 calc PR A 2
C13B C 0.0641(16) -0.0268(13) 0.7356(12) 0.037 Uiso 0.244(3) 1 d PD A 2
H13B H -0.0288 -0.0181 0.6963 0.044 Uiso 0.244(3) 1 calc PR A 2
C14B C 0.0300(16) 0.2853(16) 0.8430(8) 0.037 Uiso 0.244(3) 1 d PD A 2
C15B C 0.014(2) 0.187(3) 0.9172(13) 0.037 Uiso 0.244(3) 1 d PD A 2
H15B H 0.0806 0.1280 0.9290 0.044 Uiso 0.244(3) 1 calc PR A 2
C16B C -0.1039(15) 0.1778(13) 0.9731(10) 0.037 Uiso 0.244(3) 1 d PD A 2
H16B H -0.1297 0.0998 1.0175 0.044 Uiso 0.244(3) 1 calc PR A 2
C17B C -0.1851(15) 0.2804(14) 0.9654(8) 0.037 Uiso 0.244(3) 1 d PD A 2
H17B H -0.2513 0.2847 1.0101 0.044 Uiso 0.244(3) 1 calc PR A 2
C18B C -0.1657(14) 0.3765(14) 0.8900(7) 0.037 Uiso 0.244(3) 1 d PD A 2
H18B H -0.2276 0.4399 0.8806 0.044 Uiso 0.244(3) 1 calc PR A 2
C19B C -0.0575(14) 0.3818(14) 0.8282(7) 0.037 Uiso 0.244(3) 1 d PD A 2
H19B H -0.0440 0.4487 0.7778 0.044 Uiso 0.244(3) 1 calc PR A 2
H2B H 0.0912 0.2118 0.6171 0.044 Uiso 0.756(3) 1 d PRD A 1


_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
C1 O1 1.4422(11) . ?
C1 C14 1.5318(11) . ?
C1 C8 1.5319(11) . ?
C1 C2 1.5319(12) . ?
O1 H2B 0.9690 . ?
N25 C24 1.337(4) . ?
N25 C23 1.340(3) . ?
N25 H25 0.8800 . ?
C2 C7 1.399(5) . ?
C2 C3 1.403(5) . ?
C8 C9 1.394(5) . ?
C8 C13 1.413(5) . ?
C14 C15 1.393(5) . ?
C14 C19 1.397(5) . ?
C23 C22 1.379(4) . ?
C23 C25 1.482(4) . ?
C15 C16 1.397(5) . ?
C15 H15 0.9500 . ?
C3 C4 1.382(5) . ?
C3 H3 0.9500 . ?
C9 C10 1.394(5) . ?
C9 H9 0.9500 . ?
C7 C6 1.387(5) . ?
C7 H7 0.9500 . ?
C6 C5 1.384(5) . ?
C6 H6 0.9500 . ?
C5 C4 1.390(5) . ?
C5 H5 0.9500 . ?
C10 C11 1.384(5) . ?
C10 H10 0.9500 . ?
C19 C18 1.388(5) . ?
C19 H19 0.9500 . ?
C13 C12 1.386(5) . ?
C13 H13 0.9500 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C18 C17 1.384(5) . ?
C18 H18 0.9500 . ?
C22 C21 1.368(5) . ?
C22 H22 0.9500 . ?
C12 H12 0.9500 . ?
C17 H17 0.9500 . ?
C24 C20 1.371(4) . ?
C24 H24 0.9500 . ?
C21 C20 1.373(5) . ?
C21 H21 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C20 H20 0.9500 . ?
Si1 O2 1.6297(11) . ?
Si1 C2B 1.8690(14) . ?
Si1 C8B 1.8692(11) . ?
Si1 C14B 1.8693(11) . ?
O2 H2 0.8400 . ?
O2 H2B 0.8399 . ?
C2B C7B 1.3998(12) . ?
C2B C3B 1.3998(11) . ?
C3B C4B 1.3999(12) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3995(12) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3995(11) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.4000(12) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C8B C13B 1.3994(13) . ?
C8B C9B 1.3996(11) . ?
C9B C10B 1.4001(11) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3999(13) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3999(11) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3998(11) . ?
C12B H12B 0.9500 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3999(11) . ?
C14B C19B 1.4000(11) . ?
C15B C16B 1.3998(11) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3999(11) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3998(11) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.4000(11) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?

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 C1 C14 103.3(3) . . ?
O1 C1 C8 108.0(3) . . ?
C14 C1 C8 112.2(3) . . ?
O1 C1 C2 108.8(3) . . ?
C14 C1 C2 111.5(3) . . ?
C8 C1 C2 112.5(3) . . ?
C1 O1 H2B 129.3 . . ?
C24 N25 C23 123.4(2) . . ?
C24 N25 H25 118.3 . . ?
C23 N25 H25 118.3 . . ?
C7 C2 C3 116.6(3) . . ?
C7 C2 C1 121.6(3) . . ?
C3 C2 C1 121.8(3) . . ?
C9 C8 C13 113.4(3) . . ?
C9 C8 C1 122.3(3) . . ?
C13 C8 C1 124.1(3) . . ?
C15 C14 C19 116.0(4) . . ?
C15 C14 C1 123.7(3) . . ?
C19 C14 C1 120.3(3) . . ?
N25 C23 C22 117.6(3) . . ?
N25 C23 C25 117.7(2) . . ?
C22 C23 C25 124.7(3) . . ?
C14 C15 C16 122.6(4) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C8 C9 C10 123.6(4) . . ?
C8 C9 H9 118.2 . . ?
C10 C9 H9 118.2 . . ?
C6 C7 C2 122.2(4) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C18 C19 C14 122.2(4) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?
C12 C13 C8 125.1(4) . . ?
C12 C13 H13 117.4 . . ?
C8 C13 H13 117.4 . . ?
C17 C16 C15 119.5(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C13 C12 C11 118.2(4) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C16 C17 C18 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
N25 C24 C20 119.7(3) . . ?
N25 C24 H24 120.1 . . ?
C20 C24 H24 120.1 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C20 C21 118.6(3) . . ?
C24 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
O2 Si1 C2B 112.1(6) . . ?
O2 Si1 C8B 115.0(6) . . ?
C2B Si1 C8B 107.0(6) . . ?
O2 Si1 C14B 108.2(6) . . ?
C2B Si1 C14B 108.6(6) . . ?
C8B Si1 C14B 105.6(7) . . ?
Si1 O2 H2 109.5 . . ?
Si1 O2 H2B 107.4 . . ?
H2 O2 H2B 54.1 . . ?
C7B C2B C3B 119.5(7) . . ?
C7B C2B Si1 122.7(6) . . ?
C3B C2B Si1 117.8(6) . . ?
C2B C3B C4B 119.4(9) . . ?
C2B C3B H3B 120.3 . . ?
C4B C3B H3B 120.3 . . ?
C5B C4B C3B 123.6(11) . . ?
C5B C4B H4B 118.2 . . ?
C3B C4B H4B 118.2 . . ?
C6B C5B C4B 114.5(10) . . ?
C6B C5B H5B 122.7 . . ?
C4B C5B H5B 122.7 . . ?
C5B C6B C7B 124.5(11) . . ?
C5B C6B H6B 117.7 . . ?
C7B C6B H6B 117.7 . . ?
C2B C7B C6B 118.5(9) . . ?
C2B C7B H7B 120.8 . . ?
C6B C7B H7B 120.8 . . ?
C13B C8B C9B 132.8(7) . . ?
C13B C8B Si1 102.1(6) . . ?
C9B C8B Si1 125.1(7) . . ?
C8B C9B C10B 113.0(10) . . ?
C8B C9B H9B 123.5 . . ?
C10B C9B H9B 123.5 . . ?
C11B C10B C9B 121.1(12) . . ?
C11B C10B H10B 119.4 . . ?
C9B C10B H10B 119.4 . . ?
C10B C11B C12B 118.1(12) . . ?
C10B C11B H11B 121.0 . . ?
C12B C11B H11B 120.9 . . ?
C13B C12B C11B 127.1(12) . . ?
C13B C12B H12B 116.5 . . ?
C11B C12B H12B 116.5 . . ?
C8B C13B C12B 107.1(10) . . ?
C8B C13B H13B 126.4 . . ?
C12B C13B H13B 126.4 . . ?
C15B C14B C19B 122.5(7) . . ?
C15B C14B Si1 117.8(7) . . ?
C19B C14B Si1 119.7(6) . . ?
C14B C15B C16B 117.4(11) . . ?
C14B C15B H15B 121.3 . . ?
C16B C15B H15B 121.3 . . ?
C17B C16B C15B 121.9(12) . . ?
C17B C16B H16B 119.0 . . ?
C15B C16B H16B 119.0 . . ?
C18B C17B C16B 118.0(10) . . ?
C18B C17B H17B 121.0 . . ?
C16B C17B H17B 121.0 . . ?
C17B C18B C19B 121.8(10) . . ?
C17B C18B H18B 119.1 . . ?
C19B C18B H18B 119.1 . . ?
C18B C19B C14B 117.8(8) . . ?
C18B C19B H19B 121.1 . . ?
C14B C19B H19B 121.1 . . ?

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 Cl1 0.84 2.29 3.008(10) 143.5 .
O1 H2B Cl1 0.97 2.31 3.182(4) 149.6 .
N25 H25 Cl1 0.88 2.17 3.046(2) 171.3 1_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.96
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.089
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.060
