#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:18:03 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179889 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/85/7018580.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_7018580
loop_
_publ_author_name
'Gessner, Viktoria H.'
'Strohmann, Carsten'
_publ_section_title
;
 Preparation of aminomethyl functionalised silanes via an α-lithiated
 amine: From their synthesis, stability and crystal structures to
 stereochemical issues.
;
_journal_issue                   12
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3452
_journal_page_last               3460
_journal_paper_doi               10.1039/c2dt12163h
_journal_volume                  41
_journal_year                    2012
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C39 H52 Br2 N2 O Si2 Zn'
_chemical_formula_weight         846.2
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-10-06T13:04:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2947(4)
_cell_length_b                   16.4427(5)
_cell_length_c                   19.7658(6)
_cell_measurement_temperature    173(2)
_cell_volume                     3995.8(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_molecular_graphics    'Ortep-3 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0456
_diffrn_reflns_av_unetI/netI     0.056
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33648
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    2.706
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9125
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0115P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0397
_reflns_number_gt                5690
_reflns_number_total             7038
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt12163h.txt
_cod_data_source_block           0188
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7018580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
Br1 Br 0.96509(3) 0.710478(17) -0.005482(14) 0.03586(9) Uani 1 1 d .
Br2 Br 1.01550(3) 0.471552(18) -0.027195(14) 0.04462(10) Uani 1 1 d .
C1 C 1.2324(3) 0.5226(2) 0.07778(14) 0.0480(10) Uani 1 1 d .
H1A H 1.2411 0.5181 0.0286 0.072 Uiso 1 1 calc R
H1B H 1.1957 0.474 0.0951 0.072 Uiso 1 1 calc R
H1C H 1.304 0.5277 0.0991 0.072 Uiso 1 1 calc R
C2 C 1.2282(3) 0.6686(2) 0.07189(15) 0.0521(10) Uani 1 1 d .
H2A H 1.1845 0.7174 0.0804 0.078 Uiso 1 1 calc R
H2B H 1.2445 0.6646 0.0235 0.078 Uiso 1 1 calc R
H2C H 1.2963 0.672 0.0975 0.078 Uiso 1 1 calc R
C3 C 1.1388(2) 0.60187(18) 0.16772(12) 0.0248(8) Uani 1 1 d .
H3 H 1.1187 0.6598 0.1766 0.03 Uiso 1 1 calc R
C4 C 1.2359(2) 0.5815(2) 0.21381(13) 0.0366(8) Uani 1 1 d .
H4A H 1.2603 0.5253 0.2047 0.044 Uiso 1 1 calc R
H4B H 1.2969 0.6187 0.2034 0.044 Uiso 1 1 calc R
C5 C 1.2059(2) 0.5896(2) 0.28824(13) 0.0371(8) Uani 1 1 d .
H5A H 1.2688 0.5739 0.3167 0.045 Uiso 1 1 calc R
H5B H 1.1872 0.6468 0.2985 0.045 Uiso 1 1 calc R
C6 C 1.1110(2) 0.53576(18) 0.30400(13) 0.0319(8) Uani 1 1 d .
H6A H 1.0918 0.5411 0.3524 0.038 Uiso 1 1 calc R
H6B H 1.1309 0.4784 0.2953 0.038 Uiso 1 1 calc R
C7 C 1.0135(2) 0.55873(15) 0.26071(11) 0.0243(7) Uani 1 1 d .
H7A H 0.9921 0.6156 0.2706 0.029 Uiso 1 1 calc R
H7B H 0.9513 0.523 0.2721 0.029 Uiso 1 1 calc R
C8 C 1.0402(2) 0.55035(15) 0.18530(11) 0.0197(7) Uani 1 1 d .
H8 H 1.0609 0.4923 0.1773 0.024 Uiso 1 1 calc R
C9 C 0.8884(2) 0.64554(15) 0.15936(13) 0.0208(7) Uani 1 1 d .
H9A H 0.8351 0.6603 0.1246 0.031 Uiso 1 1 calc R
H9B H 0.9422 0.6892 0.1639 0.031 Uiso 1 1 calc R
H9C H 0.8512 0.6375 0.2027 0.031 Uiso 1 1 calc R
C10 C 0.8661(2) 0.49916(16) 0.13998(12) 0.0199(7) Uani 1 1 d .
H10A H 0.8535 0.4844 0.1879 0.024 Uiso 1 1 calc R
H10B H 0.9032 0.4523 0.1186 0.024 Uiso 1 1 calc R
C11 C 0.6353(2) 0.57059(16) 0.15391(13) 0.0209(7) Uani 1 1 d .
C12 C 0.5832(2) 0.64060(17) 0.13187(13) 0.0216(7) Uani 1 1 d .
H12 H 0.5936 0.6577 0.0864 0.026 Uiso 1 1 calc R
C13 C 0.5168(2) 0.68645(16) 0.17353(13) 0.0304(7) Uani 1 1 d .
H13 H 0.4827 0.7342 0.1566 0.037 Uiso 1 1 calc R
C14 C 0.5001(2) 0.66252(18) 0.24014(13) 0.0309(8) Uani 1 1 d .
H14 H 0.4542 0.6933 0.2691 0.037 Uiso 1 1 calc R
C15 C 0.5512(2) 0.5931(2) 0.26353(14) 0.0331(8) Uani 1 1 d .
H15 H 0.5401 0.576 0.3089 0.04 Uiso 1 1 calc R
C16 C 0.6178(2) 0.54858(18) 0.22195(13) 0.0264(7) Uani 1 1 d .
H16 H 0.653 0.5017 0.2395 0.032 Uiso 1 1 calc R
C17 C 0.6765(3) 0.40121(18) 0.09564(13) 0.0263(8) Uani 1 1 d .
C18 C 0.5744(3) 0.38047(19) 0.11825(14) 0.0420(10) Uani 1 1 d .
H18 H 0.5292 0.4213 0.1374 0.05 Uiso 1 1 calc R
C19 C 0.5360(4) 0.3015(2) 0.11383(15) 0.0692(14) Uani 1 1 d .
H19 H 0.4654 0.2884 0.1301 0.083 Uiso 1 1 calc R
C20 C 0.6006(4) 0.2421(2) 0.08574(18) 0.0733(16) Uani 1 1 d .
H20 H 0.5743 0.1879 0.0825 0.088 Uiso 1 1 calc R
C21 C 0.7040(4) 0.2610(2) 0.06208(17) 0.0659(13) Uani 1 1 d .
H21 H 0.7489 0.22 0.0428 0.079 Uiso 1 1 calc R
C22 C 0.7405(3) 0.34003(19) 0.06709(14) 0.0404(9) Uani 1 1 d .
H22 H 0.8109 0.3532 0.0507 0.048 Uiso 1 1 calc R
C23 C 0.7342(2) 0.55245(15) 0.01152(11) 0.0207(7) Uani 1 1 d .
H23A H 0.803 0.5333 -0.009 0.025 Uiso 1 1 calc R
H23B H 0.7403 0.6122 0.0163 0.025 Uiso 1 1 calc R
C24 C 0.6285(2) 0.42292(17) -0.07996(12) 0.0224(7) Uani 1 1 d .
C25 C 0.5467(3) 0.36755(17) -0.06560(12) 0.0294(8) Uani 1 1 d .
H25 H 0.4871 0.3844 -0.0384 0.035 Uiso 1 1 calc R
C26 C 0.5491(3) 0.28819(19) -0.08966(14) 0.0385(9) Uani 1 1 d .
H26 H 0.4919 0.2516 -0.0787 0.046 Uiso 1 1 calc R
C27 C 0.6350(3) 0.26242(19) -0.12972(14) 0.0375(9) Uani 1 1 d .
H27 H 0.6373 0.2083 -0.1465 0.045 Uiso 1 1 calc R
C28 C 0.7164(3) 0.31614(19) -0.14476(15) 0.0354(9) Uani 1 1 d .
H28 H 0.7755 0.2992 -0.1724 0.042 Uiso 1 1 calc R
C29 C 0.7138(3) 0.39546(19) -0.12006(13) 0.0308(8) Uani 1 1 d .
H29 H 0.7715 0.4316 -0.1309 0.037 Uiso 1 1 calc R
C30 C 0.6476(2) 0.59836(17) -0.12677(12) 0.0216(7) Uani 1 1 d .
C31 C 0.5616(3) 0.63132(16) -0.16406(13) 0.0301(8) Uani 1 1 d .
H31 H 0.4894 0.6251 -0.1478 0.036 Uiso 1 1 calc R
C32 C 0.5789(3) 0.67307(18) -0.22446(15) 0.0413(10) Uani 1 1 d .
H32 H 0.5189 0.6941 -0.2493 0.05 Uiso 1 1 calc R
C33 C 0.6833(4) 0.68370(18) -0.24795(15) 0.0425(10) Uani 1 1 d .
H33 H 0.6955 0.7112 -0.2895 0.051 Uiso 1 1 calc R
C34 C 0.7705(3) 0.6544(2) -0.21109(16) 0.0382(9) Uani 1 1 d .
H34 H 0.8426 0.6634 -0.2267 0.046 Uiso 1 1 calc R
C35 C 0.7531(3) 0.61205(17) -0.15159(14) 0.0292(8) Uani 1 1 d .
H35 H 0.8137 0.5918 -0.127 0.035 Uiso 1 1 calc R
C36 C 0.4847(2) 0.55211(14) -0.01583(11) 0.0277(7) Uani 1 1 d .
H36A H 0.4296 0.5323 -0.0477 0.042 Uiso 1 1 calc R
H36B H 0.4753 0.6107 -0.009 0.042 Uiso 1 1 calc R
H36C H 0.4765 0.5239 0.0275 0.042 Uiso 1 1 calc R
N1 N 1.16638(19) 0.59530(16) 0.09369(10) 0.0286(6) Uani 1 1 d .
N2 N 0.94444(17) 0.56883(12) 0.13944(9) 0.0161(5) Uani 1 1 d .
Si1 Si 0.72703(7) 0.50909(5) 0.09817(4) 0.0202(2) Uani 1 1 d .
Si2 Si 0.62297(6) 0.53191(5) -0.05076(4) 0.02133(19) Uani 1 1 d .
Zn1 Zn 1.01688(3) 0.586595(18) 0.044392(13) 0.02300(9) Uani 1 1 d .
C38 C 0.2987(4) 0.3577(2) 0.3051(2) 0.0536(11) Uani 1 1 d .
C39 C 0.2743(3) 0.3514(2) 0.37798(16) 0.0566(11) Uani 1 1 d .
H39A H 0.2013 0.3287 0.3841 0.085 Uiso 1 1 calc R
H39B H 0.2778 0.4055 0.3986 0.085 Uiso 1 1 calc R
H39C H 0.3278 0.3157 0.3997 0.085 Uiso 1 1 calc R
O1 O 0.2357(3) 0.3355(2) 0.26363(15) 0.1190(14) Uani 1 1 d .
C37 C 0.4049(4) 0.3957(3) 0.2887(2) 0.1010(18) Uani 1 1 d .
H37A H 0.4241 0.3836 0.2417 0.152 Uiso 1 1 calc R
H37B H 0.4611 0.3738 0.3188 0.152 Uiso 1 1 calc R
H37C H 0.3998 0.4547 0.2949 0.152 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 0 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
N1 C3 C8 111.2(2)
N1 C3 C4 112.7(2)
C8 C3 C4 111.2(2)
C5 C4 C3 111.5(2)
C6 C5 C4 109.8(2)
C5 C6 C7 110.5(2)
C6 C7 C8 110.8(2)
N2 C8 C3 111.78(19)
N2 C8 C7 113.4(2)
C3 C8 C7 110.1(2)
N2 C10 Si1 120.57(17)
C12 C11 C16 116.2(3)
C12 C11 Si1 122.8(2)
C16 C11 Si1 121.0(2)
C13 C12 C11 122.5(2)
C12 C13 C14 119.8(3)
C15 C14 C13 118.9(3)
C16 C15 C14 120.8(3)
C15 C16 C11 121.7(3)
C18 C17 C22 117.8(3)
C18 C17 Si1 121.8(3)
C22 C17 Si1 120.3(2)
C17 C18 C19 121.6(4)
C20 C19 C18 119.6(4)
C19 C20 C21 120.4(4)
C22 C21 C20 118.9(4)
C21 C22 C17 121.7(4)
Si1 C23 Si2 120.21(13)
C25 C24 C29 116.8(3)
C25 C24 Si2 122.4(2)
C29 C24 Si2 120.7(2)
C24 C25 C26 122.1(3)
C27 C26 C25 119.9(3)
C28 C27 C26 119.0(3)
C27 C28 C29 120.7(3)
C24 C29 C28 121.5(3)
C31 C30 C35 116.9(3)
C31 C30 Si2 121.6(2)
C35 C30 Si2 121.4(2)
C32 C31 C30 121.8(3)
C33 C32 C31 119.6(3)
C32 C33 C34 120.1(3)
C33 C34 C35 120.2(3)
C34 C35 C30 121.4(3)
C1 N1 C2 108.2(2)
C1 N1 C3 112.8(2)
C2 N1 C3 109.8(2)
C1 N1 Zn1 109.21(19)
C2 N1 Zn1 111.75(18)
C3 N1 Zn1 105.10(16)
C9 N2 C10 110.4(2)
C9 N2 C8 111.74(19)
C10 N2 C8 110.00(18)
C9 N2 Zn1 108.35(14)
C10 N2 Zn1 112.70(15)
C8 N2 Zn1 103.49(14)
C23 Si1 C11 111.33(12)
C23 Si1 C17 110.68(11)
C11 Si1 C17 109.02(13)
C23 Si1 C10 112.98(12)
C11 Si1 C10 109.35(12)
C17 Si1 C10 103.14(13)
C36 Si2 C23 112.99(11)
C36 Si2 C30 109.82(12)
C23 Si2 C30 107.62(12)
C36 Si2 C24 108.41(12)
C23 Si2 C24 110.30(12)
C30 Si2 C24 107.57(11)
N1 Zn1 N2 88.01(8)
N1 Zn1 Br1 112.04(7)
N2 Zn1 Br1 112.39(6)
N1 Zn1 Br2 109.95(7)
N2 Zn1 Br2 114.93(6)
Br1 Zn1 Br2 116.150(15)
O1 C38 C39 121.4(4)
O1 C38 C37 123.6(4)
C39 C38 C37 115.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 Zn1 2.3508(4)
Br2 Zn1 2.3623(4)
C1 N1 1.478(4)
C2 N1 1.489(4)
C3 N1 1.506(3)
C3 C8 1.519(4)
C3 C4 1.538(4)
C4 C5 1.522(4)
C5 C6 1.497(4)
C6 C7 1.520(3)
C7 C8 1.533(3)
C8 N2 1.517(3)
C9 N2 1.490(3)
C10 N2 1.497(3)
C10 Si1 1.906(3)
C11 C12 1.387(3)
C11 C16 1.409(3)
C11 Si1 1.873(3)
C12 C13 1.383(4)
C13 C14 1.389(3)
C14 C15 1.382(4)
C15 C16 1.372(4)
C17 C18 1.374(4)
C17 C22 1.397(4)
C17 Si1 1.880(3)
C18 C19 1.385(4)
C19 C20 1.375(5)
C20 C21 1.390(5)
C21 C22 1.379(4)
C23 Si1 1.857(2)
C23 Si2 1.870(2)
C24 C25 1.386(4)
C24 C29 1.389(4)
C24 Si2 1.884(3)
C25 C26 1.389(4)
C26 C27 1.387(4)
C27 C28 1.368(4)
C28 C29 1.393(4)
C30 C31 1.398(4)
C30 C35 1.404(4)
C30 Si2 1.882(3)
C31 C32 1.393(4)
C32 C33 1.377(5)
C33 C34 1.383(5)
C34 C35 1.383(4)
C36 Si2 1.864(2)
N1 Zn1 2.085(2)
N2 Zn1 2.0995(19)
C38 O1 1.186(4)
C38 C39 1.475(5)
C38 C37 1.483(5)
