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#$Date: 2016-03-21 07:01:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178545 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/52/4065281.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_4065281
loop_
_publ_author_name
'Breit, Nora C.'
'Ancelet, Travis'
'Quail, J. Wilson'
'Schatte, Gabriele'
'Müller, Jens'
_publ_section_title
;
 Synthesis of Intramolecularly Coordinated Aluminum and Gallium Compounds
 for the Preparation of [1]Ferrocenophanes
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6150
_journal_paper_doi               10.1021/om200680d
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C21 H35 Al N2 Si2'
_chemical_formula_sum            'C21 H35 Al N2 Si2'
_chemical_formula_weight         398.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.745(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.387(5)
_cell_length_b                   12.116(4)
_cell_length_c                   12.202(4)
_cell_measurement_reflns_used    129
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.27
_cell_measurement_theta_min      5.47
_cell_volume                     2400.5(13)
_computing_cell_refinement
'Saint V7.53A and SADABS V2008/1 (Apex2, v2009.3-0; Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2009, 9, 0, 0'
_computing_data_reduction
'Saint V7.53A and SADABS V2008/1 (Apex2, v2009.3-0, Bruker AXS)'
_computing_molecular_graphics
' Cameron (WinGX v1.80.05 2009), XP (SHELXTL-NT v6.14, Bruker AXS)'
_computing_publication_material  'WinGX v1.80.05 2009 (L. J. Farrugia)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
; SIR-2004 (M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
  G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori
  and R. Spagna, 2005) 
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       '62mm 4K CCD camera on D85 goniostat'
_diffrn_measurement_device_type  'Proteum R Smart 6000 (Bruker AXS)'
_diffrn_measurement_method       'CCD rotation images, φ and ω scans'
_diffrn_radiation_monochromator  'Montel200 multilayer graded optics'
_diffrn_radiation_source         'Bruker AXS FR591, fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_sigmaI/netI    0.1696
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6920
_diffrn_reflns_theta_full        69.61
_diffrn_reflns_theta_max         69.61
_diffrn_reflns_theta_min         4.55
_exptl_absorpt_coefficient_mu    1.736
_exptl_absorpt_correction_T_max  0.8387
_exptl_absorpt_correction_T_min  0.8175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Apex2, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0148P)²+0.9090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                1717
_reflns_number_total             2161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om200680d_si_002.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4065281
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Si1 Si 0.30492(3) 0.31489(6) 0.28256(4) 0.0493(3) Uani 1 1 d .
Al1 Al 0.5000 0.33176(9) 0.2500 0.0451(3) Uani 1 2 d S
N1 N 0.50336(10) 0.29087(19) 0.42015(14) 0.0481(5) Uani 1 1 d .
C2 C 0.44332(11) 0.2150(2) 0.39318(17) 0.0451(6) Uani 1 1 d .
C3 C 0.42808(13) 0.1340(3) 0.46988(19) 0.0549(7) Uani 1 1 d .
H3 H 0.3876 0.0787 0.4506 0.066 Uiso 1 1 calc R
C4 C 0.47321(15) 0.1363(3) 0.5743(2) 0.0631(8) Uani 1 1 d .
H4 H 0.4637 0.0821 0.6273 0.076 Uiso 1 1 calc R
C5 C 0.53165(15) 0.2164(3) 0.60172(19) 0.0657(8) Uani 1 1 d .
H5 H 0.5616 0.2195 0.6740 0.079 Uiso 1 1 calc R
C6 C 0.54600(14) 0.2924(3) 0.52226(18) 0.0605(8) Uani 1 1 d .
H6 H 0.5871 0.3472 0.5402 0.073 Uiso 1 1 calc R
C7 C 0.40256(11) 0.2337(2) 0.27825(16) 0.0435(6) Uani 1 1 d .
C8 C 0.22208(14) 0.2212(3) 0.3220(2) 0.0673(8) Uani 1 1 d .
H8A H 0.1741 0.2653 0.3349 0.081 Uiso 1 1 calc R
H8B H 0.2430 0.1810 0.3897 0.081 Uiso 1 1 calc R
H8C H 0.2059 0.1685 0.2620 0.081 Uiso 1 1 calc R
C9 C 0.26962(16) 0.3749(3) 0.1424(2) 0.0662(8) Uani 1 1 d .
H9A H 0.3110 0.4272 0.1229 0.079 Uiso 1 1 calc R
H9B H 0.2172 0.4134 0.1437 0.079 Uiso 1 1 calc R
H9C H 0.2623 0.3155 0.0874 0.079 Uiso 1 1 calc R
C10 C 0.31936(16) 0.4276(3) 0.3882(2) 0.0642(8) Uani 1 1 d .
H10A H 0.2664 0.4639 0.3925 0.077 Uiso 1 1 calc R
H10B H 0.3588 0.4818 0.3670 0.077 Uiso 1 1 calc R
H10C H 0.3404 0.3962 0.4605 0.077 Uiso 1 1 calc R
C11 C 0.38294(13) 0.1281(3) 0.21104(19) 0.0559(7) Uani 1 1 d .
H11A H 0.3474 0.0805 0.2491 0.067 Uiso 1 1 calc R
H11B H 0.4342 0.0890 0.2035 0.067 Uiso 1 1 calc R
H11C H 0.3546 0.1471 0.1375 0.067 Uiso 1 1 calc R
C12 C 0.5000 0.4962(3) 0.2500 0.0589(9) Uani 1 2 d S
H12A H 0.5340 0.5232 0.1955 0.071 Uiso 0.50 1 d PR
H12B H 0.4435 0.5232 0.2309 0.071 Uiso 0.50 1 d PR
H12C H 0.5225 0.5232 0.3236 0.071 Uiso 0.50 1 d PR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Al Al 0.2130 0.2455 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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_1
_geom_angle_site_symmetry_3
C10 Si1 C9 109.87(15) . .
C10 Si1 C8 107.02(14) . .
C9 Si1 C8 108.82(13) . .
C10 Si1 C7 111.79(11) . .
C9 Si1 C7 109.59(11) . .
C8 Si1 C7 109.68(14) . .
C12 Al1 C7 125.29(8) . 2_655
C12 Al1 C7 125.30(8) . .
C7 Al1 C7 109.41(15) 2_655 .
C12 Al1 N1 103.46(7) . 2_655
C7 Al1 N1 67.70(7) 2_655 2_655
C7 Al1 N1 96.34(8) . 2_655
C12 Al1 N1 103.46(7) . .
C7 Al1 N1 96.34(8) 2_655 .
C7 Al1 N1 67.70(7) . .
N1 Al1 N1 153.07(14) 2_655 .
C6 N1 C2 120.3(2) . .
C6 N1 Al1 147.47(16) . .
C2 N1 Al1 89.91(12) . .
N1 C2 C3 120.12(19) . .
N1 C2 C7 110.2(2) . .
C3 C2 C7 129.7(2) . .
C4 C3 C2 118.6(3) . .
C4 C3 H3 120.7 . .
C2 C3 H3 120.7 . .
C5 C4 C3 120.5(3) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 118.7(2) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
N1 C6 C5 121.7(2) . .
N1 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
C2 C7 C11 114.4(2) . .
C2 C7 Si1 109.15(14) . .
C11 C7 Si1 109.48(14) . .
C2 C7 Al1 89.18(13) . .
C11 C7 Al1 120.34(14) . .
Si1 C7 Al1 112.60(14) . .
Si1 C8 H8A 109.5 . .
Si1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
Si1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
Si1 C9 H9A 109.5 . .
Si1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
Si1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
Si1 C10 H10A 109.5 . .
Si1 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
Si1 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C7 C11 H11A 109.5 . .
C7 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C7 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
Al1 C12 H12A 109.5 . .
Al1 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
Al1 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C10 1.871(3) .
Si1 C9 1.877(3) .
Si1 C8 1.881(3) .
Si1 C7 1.885(2) .
Al1 C12 1.992(4) .
Al1 C7 2.056(2) 2_655
Al1 C7 2.056(2) .
Al1 N1 2.1280(19) 2_655
Al1 N1 2.1280(19) .
N1 C6 1.344(3) .
N1 C2 1.354(3) .
C2 C3 1.402(4) .
C2 C7 1.487(3) .
C3 C4 1.385(4) .
C3 H3 0.9500 .
C4 C5 1.373(5) .
C4 H4 0.9500 .
C5 C6 1.380(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C11 1.530(4) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9801 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C12 Al1 N1 C6 -66.3(4) .
C7 Al1 N1 C6 62.3(4) 2_655
C7 Al1 N1 C6 170.7(4) .
N1 Al1 N1 C6 113.7(4) 2_655
C12 Al1 N1 C2 134.28(13) .
C7 Al1 N1 C2 -97.09(15) 2_655
C7 Al1 N1 C2 11.33(14) .
N1 Al1 N1 C2 -45.72(13) 2_655
C6 N1 C2 C3 -3.3(3) .
Al1 N1 C2 C3 164.1(2) .
C6 N1 C2 C7 177.1(2) .
Al1 N1 C2 C7 -15.53(18) .
N1 C2 C3 C4 2.6(4) .
C7 C2 C3 C4 -177.9(2) .
C2 C3 C4 C5 0.0(4) .
C3 C4 C5 C6 -1.8(4) .
C2 N1 C6 C5 1.4(4) .
Al1 N1 C6 C5 -154.6(3) .
C4 C5 C6 N1 1.2(4) .
N1 C2 C7 C11 139.3(2) .
C3 C2 C7 C11 -40.2(3) .
N1 C2 C7 Si1 -97.61(18) .
C3 C2 C7 Si1 82.8(3) .
N1 C2 C7 Al1 16.09(19) .
C3 C2 C7 Al1 -163.5(2) .
C10 Si1 C7 C2 41.2(2) .
C9 Si1 C7 C2 163.29(19) .
C8 Si1 C7 C2 -77.3(2) .
C10 Si1 C7 C11 167.19(17) .
C9 Si1 C7 C11 -70.8(2) .
C8 Si1 C7 C11 48.65(19) .
C10 Si1 C7 Al1 -56.12(15) .
C9 Si1 C7 Al1 65.93(16) .
C8 Si1 C7 Al1 -174.66(11) .
C12 Al1 C7 C2 -101.33(14) .
C7 Al1 C7 C2 78.67(14) 2_655
N1 Al1 C7 C2 147.22(14) 2_655
N1 Al1 C7 C2 -10.30(13) .
C12 Al1 C7 C11 140.59(16) .
C7 Al1 C7 C11 -39.41(16) 2_655
N1 Al1 C7 C11 29.14(19) 2_655
N1 Al1 C7 C11 -128.4(2) .
C12 Al1 C7 Si1 9.12(13) .
C7 Al1 C7 Si1 -170.88(13) 2_655
N1 Al1 C7 Si1 -102.33(11) 2_655
N1 Al1 C7 Si1 100.15(12) .
