#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/53/24/1532477.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1532477
loop_
_publ_author_name
'Hadlington, Terrance J.'
'Hermann, Markus'
'Frenking, Gernot'
'Jones, Cameron'
_publ_section_title
;
 Two-coordinate group 14 element(ii) hydrides as reagents for the facile,
 and sometimes reversible, hydrogermylation/hydrostannylation of
 unactivated alkenes and alkynes
;
_journal_issue                   12
_journal_name_full               'Chem. Sci.'
_journal_page_first              7249
_journal_paper_doi               10.1039/C5SC03376D
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C52 H68 N Si Sn'
_chemical_formula_weight         853.85
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-09-07 deposited with the CCDC.
2015-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                99.111(7)
_cell_angle_beta                 105.293(8)
_cell_angle_gamma                95.189(7)
_cell_formula_units_Z            2
_cell_length_a                   10.2591(9)
_cell_length_b                   13.6505(10)
_cell_length_c                   17.3164(15)
_cell_measurement_temperature    123(2)
_cell_volume                     2287.3(3)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_molecular_graphics    X-Seed
_computing_publication_material  CifTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Gemini Ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_sigmaI/netI    0.1692
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17097
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SCALE3 ABSPACK'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             902
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.098
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0191P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                5584
_reflns_number_total             8971
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc03376d2.cif
_cod_data_source_block           compound13
_cod_depositor_comments
'Adding full bibliography for 1532469--1532486.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1532477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Sn1 Sn 0.82725(4) 0.87366(3) 0.73178(2) 0.02877(13) Uani 1 1 d .
Si1 Si 0.50814(16) 0.94839(9) 0.74034(8) 0.0194(3) Uani 1 1 d .
N1 N 0.6167(4) 0.8579(3) 0.7263(2) 0.0165(9) Uani 1 1 d .
C3 C 0.4149(5) 0.6087(3) 0.6188(3) 0.0164(11) Uani 1 1 d .
H3 H 0.3671 0.5760 0.5647 0.020 Uiso 1 1 calc R
C1 C 0.5561(5) 0.7544(3) 0.7107(3) 0.0164(11) Uani 1 1 d .
C2 C 0.4892(5) 0.7032(3) 0.6301(3) 0.0178(12) Uani 1 1 d .
C44 C 0.5608(6) 1.0331(4) 0.6090(3) 0.0303(14) Uani 1 1 d .
H44A H 0.4661 1.0103 0.5762 0.045 Uiso 1 1 calc R
H44B H 0.6163 0.9795 0.6016 0.045 Uiso 1 1 calc R
H44C H 0.5966 1.0922 0.5914 0.045 Uiso 1 1 calc R
C10 C 0.5085(5) 0.7451(4) 0.5567(3) 0.0201(12) Uani 1 1 d .
H10 H 0.5070 0.8189 0.5700 0.024 Uiso 1 1 calc R
C23 C 0.6555(5) 0.7467(3) 0.8596(3) 0.0195(12) Uani 1 1 d .
H23 H 0.6484 0.8200 0.8688 0.023 Uiso 1 1 calc R
C17 C 0.3932(6) 0.7055(3) 0.4781(3) 0.0186(12) Uani 1 1 d .
C4 C 0.4072(5) 0.5603(3) 0.6818(3) 0.0189(12) Uani 1 1 d .
C16 C 0.7180(6) 0.6539(4) 0.5705(3) 0.0238(13) Uani 1 1 d .
H16 H 0.6756 0.6061 0.5938 0.029 Uiso 1 1 calc R
C11 C 0.6498(6) 0.7319(4) 0.5460(3) 0.0217(12) Uani 1 1 d .
C6 C 0.5604(5) 0.7026(3) 0.7745(3) 0.0163(11) Uani 1 1 d .
C24 C 0.6119(6) 0.7067(3) 0.9278(3) 0.0208(12) Uani 1 1 d .
C7 C 0.3085(6) 0.4651(3) 0.6665(3) 0.0247(13) Uani 1 1 d .
H7 H 0.3073 0.4262 0.6122 0.030 Uiso 1 1 calc R
C36 C 0.5178(6) 0.9861(3) 0.8531(3) 0.0219(12) Uani 1 1 d .
H36 H 0.4985 0.9217 0.8713 0.026 Uiso 1 1 calc R
C38 C 0.4084(6) 1.0489(4) 0.8706(3) 0.0346(15) Uani 1 1 d .
H38A H 0.4078 1.0519 0.9274 0.052 Uiso 1 1 calc R
H38B H 0.3187 1.0179 0.8342 0.052 Uiso 1 1 calc R
H38C H 0.4288 1.1168 0.8612 0.052 Uiso 1 1 calc R
C42 C 0.5659(6) 1.0605(3) 0.6997(3) 0.0253(13) Uani 1 1 d .
H42 H 0.6648 1.0802 0.7297 0.030 Uiso 1 1 calc R
C5 C 0.4870(5) 0.6080(3) 0.7602(3) 0.0195(12) Uani 1 1 d .
H5 H 0.4908 0.5744 0.8046 0.023 Uiso 1 1 calc R
C39 C 0.3266(5) 0.8898(3) 0.6832(3) 0.0224(12) Uani 1 1 d .
H39 H 0.3346 0.8438 0.6341 0.027 Uiso 1 1 calc R
C12 C 0.7129(6) 0.7988(4) 0.5098(3) 0.0281(14) Uani 1 1 d .
H12 H 0.6668 0.8512 0.4905 0.034 Uiso 1 1 calc R
C30 C 0.8040(6) 0.7386(4) 0.8621(3) 0.0210(12) Uani 1 1 d .
C40 C 0.2274(6) 0.9603(4) 0.6489(3) 0.0382(15) Uani 1 1 d .
H40A H 0.1370 0.9219 0.6218 0.057 Uiso 1 1 calc R
H40B H 0.2606 0.9922 0.6095 0.057 Uiso 1 1 calc R
H40C H 0.2211 1.0120 0.6936 0.057 Uiso 1 1 calc R
C22 C 0.2721(6) 0.7453(4) 0.4638(3) 0.0247(13) Uani 1 1 d .
H22 H 0.2610 0.7986 0.5030 0.030 Uiso 1 1 calc R
C41 C 0.2573(6) 0.8213(4) 0.7287(3) 0.0291(13) Uani 1 1 d .
H41A H 0.2449 0.8618 0.7776 0.044 Uiso 1 1 calc R
H41B H 0.3150 0.7702 0.7445 0.044 Uiso 1 1 calc R
H41C H 0.1682 0.7885 0.6927 0.044 Uiso 1 1 calc R
C45 C 0.8970(6) 1.0295(4) 0.7888(3) 0.0306(14) Uani 1 1 d .
H45 H 0.8244 1.0599 0.8093 0.037 Uiso 1 1 calc R
C20 C 0.1808(6) 0.6327(4) 0.3355(3) 0.0295(14) Uani 1 1 d .
H20 H 0.1088 0.6079 0.2870 0.035 Uiso 1 1 calc R
C18 C 0.4081(6) 0.6283(4) 0.4191(3) 0.0264(13) Uani 1 1 d .
H18 H 0.4908 0.6001 0.4269 0.032 Uiso 1 1 calc R
C19 C 0.3013(7) 0.5931(4) 0.3493(3) 0.0354(15) Uani 1 1 d .
H19 H 0.3117 0.5400 0.3097 0.042 Uiso 1 1 calc R
C13 C 0.8423(7) 0.7898(4) 0.5016(3) 0.0398(16) Uani 1 1 d .
H13 H 0.8850 0.8372 0.4781 0.048 Uiso 1 1 calc R
C21 C 0.1666(6) 0.7092(4) 0.3935(3) 0.0308(14) Uani 1 1 d .
H21 H 0.0838 0.7373 0.3852 0.037 Uiso 1 1 calc R
C27 C 0.5228(7) 0.6364(4) 1.0499(3) 0.0357(16) Uani 1 1 d .
H27 H 0.4932 0.6123 1.0919 0.043 Uiso 1 1 calc R
C35 C 0.9091(7) 0.8101(4) 0.9122(3) 0.0341(15) Uani 1 1 d .
H35 H 0.8884 0.8642 0.9467 0.041 Uiso 1 1 calc R
C15 C 0.8469(6) 0.6443(4) 0.5616(3) 0.0355(15) Uani 1 1 d .
H15 H 0.8919 0.5906 0.5792 0.043 Uiso 1 1 calc R
C26 C 0.4432(6) 0.6934(4) 1.0021(3) 0.0307(14) Uani 1 1 d .
H26 H 0.3589 0.7087 1.0105 0.037 Uiso 1 1 calc R
C43 C 0.4990(6) 1.1552(4) 0.7151(3) 0.0371(15) Uani 1 1 d .
H43A H 0.5399 1.2087 0.6936 0.056 Uiso 1 1 calc R
H43B H 0.5135 1.1767 0.7738 0.056 Uiso 1 1 calc R
H43C H 0.4009 1.1405 0.6876 0.056 Uiso 1 1 calc R
C9 C 0.3491(7) 0.3973(4) 0.7279(3) 0.0453(19) Uani 1 1 d .
H9A H 0.4411 0.3812 0.7300 0.068 Uiso 1 1 calc R
H9B H 0.2844 0.3353 0.7113 0.068 Uiso 1 1 calc R
H9C H 0.3481 0.4315 0.7818 0.068 Uiso 1 1 calc R
C37 C 0.6582(6) 1.0333(4) 0.9079(3) 0.0313(14) Uani 1 1 d .
H37A H 0.6805 1.0998 0.8963 0.047 Uiso 1 1 calc R
H37B H 0.7262 0.9909 0.8976 0.047 Uiso 1 1 calc R
H37C H 0.6583 1.0397 0.9651 0.047 Uiso 1 1 calc R
C31 C 0.8403(6) 0.6591(4) 0.8146(3) 0.0292(13) Uani 1 1 d .
H31 H 0.7711 0.6080 0.7801 0.035 Uiso 1 1 calc R
C25 C 0.4903(6) 0.7277(4) 0.9415(3) 0.0263(13) Uani 1 1 d .
H25 H 0.4366 0.7669 0.9085 0.032 Uiso 1 1 calc R
C14 C 0.9099(6) 0.7121(4) 0.5275(3) 0.0344(14) Uani 1 1 d .
H14 H 0.9985 0.7059 0.5217 0.041 Uiso 1 1 calc R
C29 C 0.6871(6) 0.6495(4) 0.9765(3) 0.0316(14) Uani 1 1 d .
H29 H 0.7713 0.6335 0.9683 0.038 Uiso 1 1 calc R
C32 C 0.9746(7) 0.6535(4) 0.8167(3) 0.0368(15) Uani 1 1 d .
H32 H 0.9967 0.5986 0.7837 0.044 Uiso 1 1 calc R
C46 C 1.0336(7) 1.0478(5) 0.8575(4) 0.0552(19) Uani 1 1 d .
H46A H 1.0162 1.0367 0.9092 0.066 Uiso 1 1 calc R
H46B H 1.0946 1.0001 0.8434 0.066 Uiso 1 1 calc R
C28 C 0.6425(7) 0.6148(4) 1.0370(3) 0.0390(16) Uani 1 1 d .
H28 H 0.6963 0.5755 1.0700 0.047 Uiso 1 1 calc R
C33 C 1.0768(7) 0.7261(5) 0.8659(4) 0.0429(17) Uani 1 1 d .
H33 H 1.1692 0.7221 0.8671 0.051 Uiso 1 1 calc R
C8 C 0.1658(7) 0.4902(4) 0.6588(4) 0.0532(19) Uani 1 1 d .
H8A H 0.1620 0.5280 0.7111 0.080 Uiso 1 1 calc R
H8B H 0.1013 0.4282 0.6439 0.080 Uiso 1 1 calc R
H8C H 0.1415 0.5308 0.6166 0.080 Uiso 1 1 calc R
C34 C 1.0433(7) 0.8046(4) 0.9133(4) 0.0435(17) Uani 1 1 d .
H34 H 1.1131 0.8557 0.9472 0.052 Uiso 1 1 calc R
C49 C 0.9450(8) 1.0933(5) 0.7306(4) 0.061(2) Uani 1 1 d .
H49A H 0.9710 1.0485 0.6881 0.074 Uiso 1 1 calc R
H49B H 0.8686 1.1265 0.7033 0.074 Uiso 1 1 calc R
C48 C 1.0617(8) 1.1695(5) 0.7763(4) 0.057(2) Uani 1 1 d .
H48A H 1.0370 1.2376 0.7742 0.068 Uiso 1 1 calc R
H48B H 1.1398 1.1619 0.7534 0.068 Uiso 1 1 calc R
C47 C 1.0991(8) 1.1508(5) 0.8675(4) 0.069(2) Uani 1 1 d .
H47A H 1.1991 1.1568 0.8913 0.083 Uiso 1 1 calc R
H47B H 1.0615 1.1984 0.9025 0.083 Uiso 1 1 calc R
C51 C 0.0770(7) 0.5948(4) 0.1033(3) 0.0361(16) Uani 1 1 d .
H51A H 0.1005 0.5441 0.1378 0.043 Uiso 1 1 calc R
H51B H -0.0089 0.6173 0.1104 0.043 Uiso 1 1 calc R
C50 C 0.1895(6) 0.6835(4) 0.1325(3) 0.0380(16) Uani 1 1 d .
H50A H 0.2763 0.6610 0.1293 0.057 Uiso 1 1 calc R
H50B H 0.1968 0.7133 0.1891 0.057 Uiso 1 1 calc R
H50C H 0.1680 0.7336 0.0980 0.057 Uiso 1 1 calc R
C52 C 0.0534(6) 0.5463(3) 0.0151(3) 0.0312(14) Uani 1 1 d .
H52A H 0.1410 0.5277 0.0076 0.037 Uiso 1 1 calc R
H52B H 0.0254 0.5964 -0.0193 0.037 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
N1 Sn1 C45 102.78(18) .
N1 Si1 C42 107.1(2) .
N1 Si1 C39 107.8(2) .
C42 Si1 C39 112.4(2) .
N1 Si1 C36 110.9(2) .
C42 Si1 C36 110.6(2) .
C39 Si1 C36 108.0(2) .
C1 N1 Si1 116.2(3) .
C1 N1 Sn1 112.6(3) .
Si1 N1 Sn1 131.17(19) .
C4 C3 C2 123.5(4) .
C6 C1 C2 118.2(4) .
C6 C1 N1 121.1(4) .
C2 C1 N1 120.7(4) .
C3 C2 C1 118.7(4) .
C3 C2 C10 120.0(4) .
C1 C2 C10 121.1(4) .
C2 C10 C17 114.0(4) .
C2 C10 C11 110.6(4) .
C17 C10 C11 112.7(4) .
C24 C23 C30 113.8(4) .
C24 C23 C6 113.5(4) .
C30 C23 C6 110.8(4) .
C22 C17 C18 118.3(5) .
C22 C17 C10 120.8(4) .
C18 C17 C10 120.8(5) .
C3 C4 C5 116.5(4) .
C3 C4 C7 120.6(4) .
C5 C4 C7 122.8(4) .
C15 C16 C11 121.2(5) .
C16 C11 C12 118.0(5) .
C16 C11 C10 122.2(4) .
C12 C11 C10 119.9(5) .
C5 C6 C1 120.6(4) .
C5 C6 C23 119.5(4) .
C1 C6 C23 119.8(4) .
C29 C24 C25 117.5(4) .
C29 C24 C23 123.6(5) .
C25 C24 C23 118.9(5) .
C8 C7 C4 109.9(4) .
C8 C7 C9 111.9(4) .
C4 C7 C9 114.6(5) .
C37 C36 C38 110.5(4) .
C37 C36 Si1 114.7(3) .
C38 C36 Si1 115.1(3) .
C43 C42 C44 110.4(4) .
C43 C42 Si1 117.0(4) .
C44 C42 Si1 112.2(3) .
C6 C5 C4 121.8(4) .
C40 C39 C41 109.0(5) .
C40 C39 Si1 117.0(3) .
C41 C39 Si1 114.9(3) .
C13 C12 C11 120.8(5) .
C35 C30 C31 116.9(5) .
C35 C30 C23 121.2(5) .
C31 C30 C23 121.9(5) .
C17 C22 C21 121.3(5) .
C46 C45 C49 97.5(5) .
C46 C45 Sn1 114.5(4) .
C49 C45 Sn1 112.8(3) .
C19 C20 C21 118.5(5) .
C19 C18 C17 119.5(5) .
C20 C19 C18 121.9(5) .
C12 C13 C14 120.5(5) .
C20 C21 C22 120.4(6) .
C28 C27 C26 120.2(5) .
C34 C35 C30 121.5(6) .
C14 C15 C16 120.4(5) .
C27 C26 C25 118.2(5) .
C32 C31 C30 121.2(5) .
C24 C25 C26 122.3(5) .
C15 C14 C13 119.1(6) .
C24 C29 C28 121.2(6) .
C33 C32 C31 120.8(6) .
C47 C46 C45 109.5(5) .
C27 C28 C29 120.6(5) .
C34 C33 C32 118.9(6) .
C33 C34 C35 120.6(6) .
C48 C49 C45 111.1(5) .
C49 C48 C47 105.6(5) .
C46 C47 C48 102.4(6) .
C52 C51 C50 113.5(4) .
C51 C52 C52 115.0(5) 2_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Sn1 N1 2.127(4) .
Sn1 C45 2.168(5) .
Si1 N1 1.767(4) .
Si1 C42 1.894(5) .
Si1 C39 1.896(6) .
Si1 C36 1.912(4) .
N1 C1 1.445(5) .
C3 C4 1.378(6) .
C3 C2 1.394(6) .
C1 C6 1.397(6) .
C1 C2 1.416(6) .
C2 C10 1.526(6) .
C44 C42 1.542(6) .
C10 C17 1.531(7) .
C10 C11 1.532(7) .
C23 C24 1.527(6) .
C23 C30 1.527(7) .
C23 C6 1.529(6) .
C17 C22 1.379(7) .
C17 C18 1.395(6) .
C4 C5 1.405(7) .
C4 C7 1.516(6) .
C16 C15 1.386(7) .
C16 C11 1.388(7) .
C11 C12 1.390(6) .
C6 C5 1.385(6) .
C24 C29 1.376(7) .
C24 C25 1.377(7) .
C7 C8 1.511(8) .
C7 C9 1.519(6) .
C36 C37 1.519(7) .
C36 C38 1.536(7) .
C42 C43 1.536(7) .
C39 C40 1.534(7) .
C39 C41 1.553(6) .
C12 C13 1.386(8) .
C30 C35 1.384(7) .
C30 C31 1.394(7) .
C22 C21 1.384(7) .
C45 C46 1.550(9) .
C45 C49 1.574(7) .
C20 C19 1.373(8) .
C20 C21 1.375(7) .
C18 C19 1.384(7) .
C13 C14 1.387(8) .
C27 C28 1.354(8) .
C27 C26 1.386(7) .
C35 C34 1.381(8) .
C15 C14 1.375(7) .
C26 C25 1.390(6) .
C31 C32 1.379(8) .
C29 C28 1.380(7) .
C32 C33 1.372(8) .
C46 C47 1.466(8) .
C33 C34 1.369(8) .
C49 C48 1.467(9) .
C48 C47 1.592(8) .
C51 C52 1.511(7) .
C51 C50 1.516(7) .
C52 C52 1.521(10) 2_565
