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#$Date: 2016-03-21 07:41:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178577 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/87/4068789.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_4068789
loop_
_publ_author_name
'Arrowsmith, Merle'
'Hill, Michael S.'
'Kociok-Köhn, Gabriele'
_publ_section_title
;
 Bis(imidazolin-2-ylidene-1-yl)borate Complexes of the Heavier Alkaline
 Earths: Synthesis and Studies of Catalytic Hydroamination
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1730
_journal_paper_doi               10.1021/om8010933
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C24 H30 B N4, I'
_chemical_formula_sum            'C24 H30 B I N4'
_chemical_formula_weight         512.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 115.2160(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.25660(10)
_cell_length_b                   19.2495(3)
_cell_length_c                   8.84100(10)
_cell_measurement_reflns_used    30610
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      2.910
_cell_volume                     1271.25(3)
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). 
 Sheldrick, G.M., Institüt für Anorganische Chemie der Universität, 
 Tammanstrasse 4, D-3400 Göttingen, Germany, 1998 
;
_computing_structure_solution
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       '415 1.4 degree images with ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            25876
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         3.53
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.276
_exptl_absorpt_correction_T_max  0.7180
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.952
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0269
_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)+(0.0255P)²+0.7522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0630
_reflns_number_gt                3287
_reflns_number_total             3804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8010933_si_002.cif
_cod_data_source_block           k08msh49
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4068789
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
I1 I 0.22116(2) 0.2500 0.14800(2) 0.03483(6) Uani 1 2 d S
N1 N -0.30053(17) 0.31559(6) -0.29512(17) 0.0233(3) Uani 1 1 d .
N2 N -0.14312(17) 0.40427(6) -0.30816(16) 0.0225(3) Uani 1 1 d .
C1 C -0.1522(2) 0.35194(8) -0.21254(19) 0.0223(3) Uani 1 1 d .
H1A H -0.0657 0.3423 -0.1022 0.027 Uiso 1 1 calc R
C2 C -0.2927(2) 0.40070(9) -0.4586(2) 0.0317(4) Uani 1 1 d .
H2A H -0.3221 0.4313 -0.5508 0.038 Uiso 1 1 calc R
C3 C -0.3895(2) 0.34565(9) -0.4504(2) 0.0316(4) Uani 1 1 d .
H3A H -0.4996 0.3303 -0.5364 0.038 Uiso 1 1 calc R
C4 C -0.0078(2) 0.45791(8) -0.25935(19) 0.0223(3) Uani 1 1 d .
C5 C -0.0540(2) 0.52398(8) -0.2262(2) 0.0241(3) Uani 1 1 d .
C6 C 0.0750(2) 0.57580(8) -0.1842(2) 0.0255(3) Uani 1 1 d .
H6 H 0.0449 0.6217 -0.1657 0.031 Uiso 1 1 calc R
C7 C 0.2472(2) 0.56227(9) -0.1684(2) 0.0258(3) Uani 1 1 d .
C8 C 0.2873(2) 0.49528(9) -0.2011(2) 0.0282(3) Uani 1 1 d .
H8 H 0.4049 0.4855 -0.1894 0.034 Uiso 1 1 calc R
C9 C 0.1608(2) 0.44190(8) -0.2505(2) 0.0259(3) Uani 1 1 d .
C10 C -0.2358(2) 0.53908(9) -0.2319(3) 0.0341(4) Uani 1 1 d .
H10A H -0.2407 0.5877 -0.2010 0.051 Uiso 1 1 calc R
H10B H -0.2565 0.5086 -0.1532 0.051 Uiso 1 1 calc R
H10C H -0.3282 0.5308 -0.3453 0.051 Uiso 1 1 calc R
C11 C 0.3848(2) 0.61967(10) -0.1179(2) 0.0352(4) Uani 1 1 d .
H11A H 0.4981 0.6014 -0.1122 0.053 Uiso 1 1 calc R
H11B H 0.4034 0.6377 -0.0081 0.053 Uiso 1 1 calc R
H11C H 0.3424 0.6572 -0.2006 0.053 Uiso 1 1 calc R
C12 C 0.2049(2) 0.37054(9) -0.2924(3) 0.0373(4) Uani 1 1 d .
H12A H 0.2228 0.3386 -0.2002 0.056 Uiso 1 1 calc R
H12B H 0.3146 0.3728 -0.3094 0.056 Uiso 1 1 calc R
H12C H 0.1060 0.3538 -0.3948 0.056 Uiso 1 1 calc R
B1 B -0.3602(4) 0.2500 -0.2268(4) 0.0281(5) Uani 1 2 d S
H1 H -0.513(4) 0.2500 -0.285(4) 0.035(8) Uiso 1 2 d S
H2 H -0.287(4) 0.2500 -0.089(4) 0.030(7) Uiso 1 2 d S
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C1 N1 C3 107.58(13) . .
C1 N1 B1 125.51(16) . .
C3 N1 B1 126.91(16) . .
C1 N2 C2 107.67(13) . .
C1 N2 C4 126.42(13) . .
C2 N2 C4 125.78(13) . .
N1 C1 N2 109.68(13) . .
N1 C1 H1A 125.2 . .
N2 C1 H1A 125.2 . .
C3 C2 N2 107.21(14) . .
C3 C2 H2A 126.4 . .
N2 C2 H2A 126.4 . .
C2 C3 N1 107.86(14) . .
C2 C3 H3A 126.1 . .
N1 C3 H3A 126.1 . .
C5 C4 C9 123.08(14) . .
C5 C4 N2 117.91(13) . .
C9 C4 N2 119.01(13) . .
C6 C5 C4 117.62(14) . .
C6 C5 C10 120.60(14) . .
C4 C5 C10 121.76(14) . .
C5 C6 C7 121.75(15) . .
C5 C6 H6 119.1 . .
C7 C6 H6 119.1 . .
C8 C7 C6 118.38(14) . .
C8 C7 C11 121.60(15) . .
C6 C7 C11 120.02(15) . .
C7 C8 C9 122.30(14) . .
C7 C8 H8 118.8 . .
C9 C8 H8 118.8 . .
C4 C9 C8 116.79(14) . .
C4 C9 C12 121.81(14) . .
C8 C9 C12 121.40(14) . .
C5 C10 H10A 109.5 . .
C5 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C5 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 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N1 B1 N1 107.38(18) . 4_565
N1 B1 H1 107.1(8) . .
N1 B1 H1 107.1(8) 4_565 .
N1 B1 H2 108.1(8) . .
N1 B1 H2 108.1(8) 4_565 .
H1 B1 H2 119(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3267(19) .
N1 C3 1.379(2) .
N1 B1 1.567(2) .
N2 C1 1.3376(19) .
N2 C2 1.378(2) .
N2 C4 1.4459(19) .
C1 H1A 0.9500 .
C2 C3 1.348(2) .
C2 H2A 0.9500 .
C3 H3A 0.9500 .
C4 C5 1.394(2) .
C4 C9 1.395(2) .
C5 C6 1.389(2) .
C5 C10 1.508(2) .
C6 C7 1.393(2) .
C6 H6 0.9500 .
C7 C8 1.392(2) .
C7 C11 1.509(2) .
C8 C9 1.396(2) .
C8 H8 0.9500 .
C9 C12 1.507(2) .
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 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
B1 N1 1.567(2) 4_565
B1 H1 1.14(3) .
B1 H2 1.11(3) .
