#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:32:09 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179975 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/69/7026963.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_7026963
loop_
_publ_author_name
'Dickschat, Julia V.'
'Urban, Slawomir'
'Pape, Tania'
'Glorius, Frank'
'Hahn, F. Ekkehardt'
_publ_section_title
;
 Sterically demanding and chiral N,N'-disubstituted N-heterocyclic
 germylenes and stannylenes.
;
_journal_issue                   48
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11519
_journal_page_last               11521
_journal_paper_doi               10.1039/c0dt01233e
_journal_volume                  39
_journal_year                    2010
_chemical_formula_sum            'C24 H26 N2 Sn'
_chemical_formula_weight         461.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3800(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4015(3)
_cell_length_b                   11.3645(3)
_cell_length_c                   21.6208(7)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      1
_cell_volume                     2063.73(11)
_computing_cell_refinement       'APEX2(Bruker AXS, 2007)'
_computing_data_collection       'APEX2(Bruker AXS, 2007)'
_computing_data_reduction        'SAINT,SADABS (Bruker AXS, 2007 )'
_computing_molecular_graphics
;
ORTEP3,L.J. Farrugia, J. Appl. Cryst. (1997) 30, 565
;
_computing_structure_refinement
;
SHELXL-97, G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_computing_structure_solution
;
SHELXS-97 , G. M. Sheldrick, Acta Cryst. (2008) A64, 112-122
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 80
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24333
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_T_max  0.8545
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Corrections were done with the SADABS program, utilizing the none merged
raw data obtained from the integration process. Integration and final cell
refinement were done with SAINT.

SADABS reports ratio of Tmin/Tmax = 0.834630

;
_exptl_crystal_colour            gold-orange
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent rhombus'
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         6277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0233
_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)+(0.0270P)²+0.9414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0599
_reflns_number_gt                5589
_reflns_number_total             6277
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01233e.txt
_cod_data_source_block           cif-2
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7026963
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
C1 C 0.58850(17) 0.41145(13) 0.22068(7) 0.0193(3) Uani 1 1 d .
C2 C 0.66222(18) 0.44748(13) 0.16502(7) 0.0191(3) Uani 1 1 d .
C3 C 0.7262(2) 0.36188(15) 0.12648(7) 0.0236(3) Uani 1 1 d .
H3 H 0.7784 0.3850 0.0899 0.028 Uiso 1 1 calc R
C4 C 0.7142(2) 0.24305(14) 0.14112(8) 0.0269(3) Uani 1 1 d .
H4 H 0.7602 0.1858 0.1150 0.032 Uiso 1 1 calc R
C5 C 0.6352(2) 0.20759(14) 0.19380(8) 0.0264(3) Uani 1 1 d .
H5 H 0.6238 0.1262 0.2027 0.032 Uiso 1 1 calc R
C6 C 0.57276(19) 0.29162(14) 0.23352(7) 0.0233(3) Uani 1 1 d .
H6 H 0.5192 0.2672 0.2695 0.028 Uiso 1 1 calc R
C7 C 0.45070(18) 0.47230(13) 0.31284(7) 0.0192(3) Uani 1 1 d .
C8 C 0.28345(19) 0.47609(14) 0.31187(7) 0.0233(3) Uani 1 1 d .
C9 C 0.2035(2) 0.45521(15) 0.36632(8) 0.0278(3) Uani 1 1 d .
H9 H 0.0905 0.4577 0.3659 0.033 Uiso 1 1 calc R
C10 C 0.2858(2) 0.43070(15) 0.42149(7) 0.0280(3) Uani 1 1 d .
C11 C 0.4502(2) 0.42245(14) 0.42077(7) 0.0259(3) Uani 1 1 d .
H11 H 0.5068 0.4033 0.4580 0.031 Uiso 1 1 calc R
C12 C 0.53546(19) 0.44144(13) 0.36695(7) 0.0215(3) Uani 1 1 d .
C13 C 0.1908(2) 0.50109(19) 0.25272(8) 0.0341(4) Uani 1 1 d .
H13A H 0.0803 0.4755 0.2571 0.051 Uiso 1 1 calc R
H13B H 0.2388 0.4583 0.2185 0.051 Uiso 1 1 calc R
H13C H 0.1932 0.5857 0.2441 0.051 Uiso 1 1 calc R
C14 C 0.1972(3) 0.4150(2) 0.48075(9) 0.0450(5) Uani 1 1 d .
H14A H 0.2621 0.3683 0.5100 0.068 Uiso 1 1 calc R
H14B H 0.0964 0.3742 0.4720 0.068 Uiso 1 1 calc R
H14C H 0.1756 0.4922 0.4989 0.068 Uiso 1 1 calc R
C15 C 0.7133(2) 0.42443(15) 0.36776(8) 0.0261(3) Uani 1 1 d .
H15A H 0.7476 0.4039 0.3261 0.039 Uiso 1 1 calc R
H15B H 0.7423 0.3609 0.3965 0.039 Uiso 1 1 calc R
H15C H 0.7657 0.4974 0.3812 0.039 Uiso 1 1 calc R
C16 C 0.70081(18) 0.60757(13) 0.09273(7) 0.0190(3) Uani 1 1 d .
C17 C 0.85959(18) 0.62032(13) 0.07573(7) 0.0208(3) Uani 1 1 d .
C18 C 0.8914(2) 0.65933(14) 0.01588(7) 0.0239(3) Uani 1 1 d .
H18 H 0.9990 0.6664 0.0039 0.029 Uiso 1 1 calc R
C19 C 0.7711(2) 0.68807(14) -0.02659(7) 0.0247(3) Uani 1 1 d .
C20 C 0.6147(2) 0.67483(14) -0.00855(8) 0.0252(3) Uani 1 1 d .
H20 H 0.5309 0.6942 -0.0370 0.030 Uiso 1 1 calc R
C21 C 0.57671(18) 0.63386(14) 0.05027(7) 0.0221(3) Uani 1 1 d .
C22 C 0.9952(2) 0.59371(17) 0.12009(8) 0.0292(3) Uani 1 1 d .
H22A H 0.9531 0.5654 0.1593 0.044 Uiso 1 1 calc R
H22B H 1.0577 0.6653 0.1276 0.044 Uiso 1 1 calc R
H22C H 1.0634 0.5330 0.1024 0.044 Uiso 1 1 calc R
C23 C 0.8085(3) 0.73178(18) -0.09069(8) 0.0364(4) Uani 1 1 d .
H23A H 0.8422 0.8142 -0.0884 0.055 Uiso 1 1 calc R
H23B H 0.7132 0.7253 -0.1175 0.055 Uiso 1 1 calc R
H23C H 0.8943 0.6841 -0.1077 0.055 Uiso 1 1 calc R
C24 C 0.4048(2) 0.61714(18) 0.06676(9) 0.0312(4) Uani 1 1 d .
H24A H 0.3710 0.6825 0.0929 0.047 Uiso 1 1 calc R
H24B H 0.3932 0.5428 0.0892 0.047 Uiso 1 1 calc R
H24C H 0.3386 0.6152 0.0288 0.047 Uiso 1 1 calc R
N1 N 0.53269(16) 0.50139(11) 0.25756(6) 0.0203(2) Uani 1 1 d .
N2 N 0.66059(16) 0.56764(11) 0.15335(6) 0.0202(2) Uani 1 1 d .
Sn1 Sn 0.560669(13) 0.670251(9) 0.222550(5) 0.02266(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 C1 C6 124.76(13)
N1 C1 C2 115.70(13)
C6 C1 C2 119.51(13)
N2 C2 C3 125.35(14)
N2 C2 C1 115.66(13)
C3 C2 C1 118.97(14)
C4 C3 C2 120.61(14)
C3 C4 C5 120.39(14)
C4 C5 C6 119.96(15)
C5 C6 C1 120.42(14)
C12 C7 C8 120.57(14)
C12 C7 N1 120.67(14)
C8 C7 N1 118.76(13)
C9 C8 C7 119.05(15)
C9 C8 C13 120.04(15)
C7 C8 C13 120.91(14)
C8 C9 C10 121.31(16)
C11 C10 C9 118.61(14)
C11 C10 C14 120.95(17)
C9 C10 C14 120.44(17)
C10 C11 C12 122.01(15)
C11 C12 C7 118.30(15)
C11 C12 C15 119.90(14)
C7 C12 C15 121.77(14)
C17 C16 C21 120.24(13)
C17 C16 N2 121.29(13)
C21 C16 N2 118.47(13)
C18 C17 C16 118.67(14)
C18 C17 C22 119.69(14)
C16 C17 C22 121.64(14)
C19 C18 C17 122.30(15)
C18 C19 C20 117.88(14)
C18 C19 C23 121.33(16)
C20 C19 C23 120.80(16)
C19 C20 C21 122.01(15)
C20 C21 C16 118.87(14)
C20 C21 C24 119.86(15)
C16 C21 C24 121.26(14)
C1 N1 C7 119.10(12)
C1 N1 Sn1 115.40(9)
C7 N1 Sn1 125.30(9)
C2 N2 C16 118.40(12)
C2 N2 Sn1 114.90(9)
C16 N2 Sn1 125.81(10)
N1 Sn1 N2 78.25(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3850(19)
C1 C6 1.397(2)
C1 C2 1.427(2)
C2 N2 1.3886(19)
C2 C3 1.397(2)
C3 C4 1.391(2)
C4 C5 1.391(2)
C5 C6 1.395(2)
C7 C12 1.400(2)
C7 C8 1.406(2)
C7 N1 1.4324(18)
C8 C9 1.390(2)
C8 C13 1.508(2)
C9 C10 1.392(3)
C10 C11 1.385(3)
C10 C14 1.508(2)
C11 C12 1.398(2)
C12 C15 1.506(2)
C16 C17 1.400(2)
C16 C21 1.405(2)
C16 N2 1.4351(18)
C17 C18 1.400(2)
C17 C22 1.503(2)
C18 C19 1.388(2)
C19 C20 1.388(2)
C19 C23 1.512(2)
C20 C21 1.398(2)
C21 C24 1.508(2)
N1 Sn1 2.0783(13)
N2 Sn1 2.0890(12)
