#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:58:04 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179908 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/04/7020413.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_7020413
loop_
_publ_author_name
'Piel, Isabel'
'Dickschat, Julia V.'
'Pape, Tania'
'Hahn, F. Ekkehardt'
'Glorius, Frank'
_publ_section_title
;
 A planar chiral [2.2]paracyclophane derived N-heterocyclic stannylene.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13788
_journal_page_last               13790
_journal_paper_doi               10.1039/c2dt31497e
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C28 H24 N2 Sn'
_chemical_formula_weight         507.18
_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                 93.7083(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6317(3)
_cell_length_b                   10.4920(3)
_cell_length_c                   17.6728(5)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      22.5
_cell_measurement_theta_min      1
_cell_volume                     2152.27(10)
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25504
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_correction_T_min  0.8688
_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 = 0.848169

;
_exptl_crystal_colour            'intense orange'
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0238
_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)+(0.0330P)²+1.1486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0643
_reflns_number_gt                5658
_reflns_number_total             6557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt31497e.txt
_cod_data_source_block           sad_compound_4
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7020413
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
Sn1 Sn 0.434452(10) 0.648539(10) 0.357450(6) 0.02047(4) Uani 1 1 d .
N1 N 0.46582(12) 0.46576(14) 0.31061(8) 0.0207(3) Uani 1 1 d .
N2 N 0.30699(12) 0.58936(13) 0.43031(8) 0.0198(3) Uani 1 1 d .
C1 C 0.56922(14) 0.44715(17) 0.27562(9) 0.0225(3) Uani 1 1 d .
C2 C 0.66741(15) 0.51845(18) 0.29881(11) 0.0285(4) Uani 1 1 d .
H2 H 0.6641 0.5769 0.3397 0.034 Uiso 1 1 calc R
C3 C 0.76931(17) 0.5046(2) 0.26280(13) 0.0379(5) Uani 1 1 d .
H3 H 0.8342 0.5555 0.2783 0.045 Uiso 1 1 calc R
C4 C 0.77739(19) 0.4179(2) 0.20476(13) 0.0410(5) Uani 1 1 d .
H4 H 0.8476 0.4078 0.1808 0.049 Uiso 1 1 calc R
C5 C 0.6817(2) 0.3458(2) 0.18188(12) 0.0367(5) Uani 1 1 d .
H5 H 0.6870 0.2851 0.1424 0.044 Uiso 1 1 calc R
C6 C 0.57840(17) 0.36094(19) 0.21576(11) 0.0294(4) Uani 1 1 d .
H6 H 0.5131 0.3123 0.1982 0.035 Uiso 1 1 calc R
C7 C 0.24315(14) 0.68855(16) 0.46141(9) 0.0209(3) Uani 1 1 d .
C8 C 0.20445(15) 0.79135(18) 0.41600(11) 0.0266(3) Uani 1 1 d .
H8 H 0.2153 0.7907 0.3632 0.032 Uiso 1 1 calc R
C9 C 0.15036(17) 0.8939(2) 0.44797(13) 0.0346(4) Uani 1 1 d .
H9 H 0.1250 0.9633 0.4166 0.041 Uiso 1 1 calc R
C10 C 0.13254(17) 0.8973(2) 0.52454(13) 0.0354(4) Uani 1 1 d .
H10 H 0.0961 0.9686 0.5459 0.043 Uiso 1 1 calc R
C11 C 0.16865(16) 0.7952(2) 0.56953(12) 0.0317(4) Uani 1 1 d .
H11 H 0.1565 0.7965 0.6222 0.038 Uiso 1 1 calc R
C12 C 0.22245(15) 0.69071(18) 0.53885(10) 0.0246(3) Uani 1 1 d .
H12 H 0.2453 0.6206 0.5703 0.030 Uiso 1 1 calc R
C13 C 0.37957(14) 0.37012(16) 0.30634(9) 0.0198(3) Uani 1 1 d .
C14 C 0.26587(14) 0.41138(17) 0.29245(9) 0.0210(3) Uani 1 1 d .
H14 H 0.2522 0.4945 0.2726 0.025 Uiso 1 1 calc R
C15 C 0.17203(15) 0.33457(18) 0.30674(10) 0.0251(3) Uani 1 1 d .
C16 C 0.19266(17) 0.20422(19) 0.31573(10) 0.0288(4) Uani 1 1 d .
H16 H 0.1301 0.1459 0.3152 0.035 Uiso 1 1 calc R
C17 C 0.30595(18) 0.16006(17) 0.32556(10) 0.0275(4) Uani 1 1 d .
H17 H 0.3193 0.0709 0.3299 0.033 Uiso 1 1 calc R
C18 C 0.39978(15) 0.24233(16) 0.32916(9) 0.0225(3) Uani 1 1 d .
C19 C 0.50849(16) 0.20141(18) 0.37470(10) 0.0274(4) Uani 1 1 d .
H19A H 0.5672 0.2695 0.3731 0.033 Uiso 1 1 calc R
H19B H 0.5398 0.1237 0.3519 0.033 Uiso 1 1 calc R
C20 C 0.48288(17) 0.17377(17) 0.45952(11) 0.0272(4) Uani 1 1 d .
H20A H 0.4611 0.0831 0.4649 0.033 Uiso 1 1 calc R
H20B H 0.5533 0.1895 0.4927 0.033 Uiso 1 1 calc R
C21 C 0.38631(16) 0.25790(16) 0.48412(9) 0.0232(3) Uani 1 1 d .
C22 C 0.39187(15) 0.38955(16) 0.47223(9) 0.0206(3) Uani 1 1 d .
H22 H 0.4652 0.4298 0.4741 0.025 Uiso 1 1 calc R
C23 C 0.29322(14) 0.46385(16) 0.45770(9) 0.0199(3) Uani 1 1 d .
C24 C 0.18380(15) 0.40483(17) 0.45793(9) 0.0231(3) Uani 1 1 d .
C25 C 0.18010(16) 0.28148(18) 0.48744(10) 0.0277(4) Uani 1 1 d .
H25 H 0.1080 0.2467 0.4994 0.033 Uiso 1 1 calc R
C26 C 0.27935(17) 0.20811(18) 0.49982(10) 0.0276(4) Uani 1 1 d .
H26 H 0.2741 0.1239 0.5190 0.033 Uiso 1 1 calc R
C27 C 0.07865(15) 0.45623(19) 0.41228(11) 0.0295(4) Uani 1 1 d .
H27A H 0.0858 0.5499 0.4077 0.035 Uiso 1 1 calc R
H27B H 0.0090 0.4382 0.4399 0.035 Uiso 1 1 calc R
C28 C 0.06298(16) 0.3955(2) 0.32971(11) 0.0321(4) Uani 1 1 d .
H28A H 0.0010 0.3308 0.3288 0.039 Uiso 1 1 calc R
H28B H 0.0393 0.4630 0.2927 0.039 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'
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
N2 Sn1 N1 96.69(5)
C1 N1 C13 120.17(14)
C1 N1 Sn1 118.07(11)
C13 N1 Sn1 121.32(10)
C7 N2 C23 118.62(13)
C7 N2 Sn1 115.30(10)
C23 N2 Sn1 125.42(11)
N1 C1 C6 122.19(16)
N1 C1 C2 120.14(16)
C6 C1 C2 117.65(16)
C3 C2 C1 120.84(19)
C4 C3 C2 120.7(2)
C3 C4 C5 119.07(19)
C4 C5 C6 121.0(2)
C5 C6 C1 120.70(19)
C8 C7 C12 118.46(16)
C8 C7 N2 120.17(15)
C12 C7 N2 121.27(16)
C9 C8 C7 120.13(18)
C10 C9 C8 121.34(19)
C9 C10 C11 118.89(18)
C10 C11 C12 120.97(19)
C11 C12 C7 120.17(18)
C14 C13 C18 118.75(15)
C14 C13 N1 116.64(15)
C18 C13 N1 123.47(15)
C15 C14 C13 122.17(16)
C14 C15 C16 117.17(17)
C14 C15 C28 119.25(17)
C16 C15 C28 121.95(17)
C15 C16 C17 119.53(17)
C18 C17 C16 122.10(17)
C17 C18 C13 117.38(16)
C17 C18 C19 118.29(16)
C13 C18 C19 122.47(16)
C18 C19 C20 110.79(15)
C21 C20 C19 110.83(14)
C26 C21 C22 116.78(17)
C26 C21 C20 121.80(16)
C22 C21 C20 119.33(16)
C23 C22 C21 122.20(16)
C22 C23 N2 118.17(14)
C22 C23 C24 118.90(15)
N2 C23 C24 121.97(15)
C25 C24 C23 117.11(16)
C25 C24 C27 118.93(16)
C23 C24 C27 122.42(16)
C26 C25 C24 121.69(16)
C25 C26 C21 120.20(16)
C24 C27 C28 112.65(15)
C15 C28 C27 111.72(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Sn1 N2 2.1186(13)
Sn1 N1 2.1296(14)
N1 C1 1.401(2)
N1 C13 1.417(2)
N2 C7 1.410(2)
N2 C23 1.416(2)
C1 C6 1.401(3)
C1 C2 1.404(2)
C2 C3 1.389(3)
C3 C4 1.379(3)
C4 C5 1.384(3)
C5 C6 1.386(3)
C7 C8 1.401(2)
C7 C12 1.405(2)
C8 C9 1.385(3)
C9 C10 1.383(3)
C10 C11 1.383(3)
C11 C12 1.390(3)
C13 C14 1.398(2)
C13 C18 1.415(2)
C14 C15 1.393(2)
C15 C16 1.396(3)
C15 C28 1.500(3)
C16 C17 1.397(3)
C17 C18 1.390(3)
C18 C19 1.516(2)
C19 C20 1.574(3)
C20 C21 1.514(3)
C21 C26 1.394(3)
C21 C22 1.399(2)
C22 C23 1.397(2)
C23 C24 1.416(2)
C24 C25 1.397(3)
C24 C27 1.520(3)
C25 C26 1.393(3)
C27 C28 1.592(3)
