#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:06:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178635 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/46/4074627.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_4074627
loop_
_publ_author_name
'Cortes-Llamas, Sara A.'
'Hernández-Pérez, Julio M.'
'Hô, Minhhuy'
'Muñoz-Hernández, Miguel-Ángel'
_publ_section_title
;
 Indazolato Derivatives of Boron, Aluminum, and Gallium: 
 Characterization and Solvent-Dependent Regioisomeric Structures through
 π−π Interactions in the Solid State
;
_journal_issue                   3
_journal_name_full               Organometallics
_journal_page_first              588
_journal_paper_doi               10.1021/om0506421
_journal_volume                  25
_journal_year                    2006
_chemical_formula_moiety         '[(h1,h1-ind)(m-B)Et2]2'
_chemical_formula_sum            'C28 H36 B2 N4'
_chemical_formula_weight         450.23
_chemical_melting_point          '176-177 &#x00B0;C'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 115.279(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.243(4)
_cell_length_b                   8.693(2)
_cell_length_c                   18.430(4)
_cell_measurement_temperature    100(2)
_cell_volume                     2498.0(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.759
_diffrn_measured_fraction_theta_max 0.759
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8457
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.070
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4732
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.118
_refine_ls_shift/su_mean         0.025
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0710P)²+0.4152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                3551
_reflns_number_total             4732
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om0506421si20050728_122356.cif
_cod_data_source_block           compound_3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2497.9(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4074627
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
B1 B 0.18494(13) 0.61133(19) 0.25398(10) 0.0175(4) Uani 1 1 d .
C18 C 0.09805(13) 0.35918(19) 0.25115(11) 0.0301(5) Uani 1 1 d .
H18A H 0.1052 0.3253 0.2048 0.045 Uiso 1 1 calc R
H18B H 0.0438 0.3239 0.2477 0.045 Uiso 1 1 calc R
H18C H 0.1434 0.3180 0.2987 0.045 Uiso 1 1 calc R
C20 C 0.28609(13) 0.14650(19) 0.21567(12) 0.0311(5) Uani 1 1 d .
H20A H 0.2735 0.1560 0.2615 0.047 Uiso 1 1 calc R
H20B H 0.3034 0.0429 0.2121 0.047 Uiso 1 1 calc R
H20C H 0.2358 0.1712 0.1679 0.047 Uiso 1 1 calc R
B2 B 0.33969(14) 0.43567(19) 0.23235(10) 0.0176(4) Uani 1 1 d .
C7 C 0.38607(12) 0.40615(17) 0.38409(9) 0.0208(4) Uani 1 1 d .
H7 H 0.4337 0.3461 0.3923 0.025 Uiso 1 1 calc R
C21 C 0.41490(12) 0.54678(17) 0.23543(10) 0.0191(4) Uani 1 1 d .
H21A H 0.4683 0.5117 0.2781 0.023 Uiso 1 1 calc R
H21B H 0.4202 0.5362 0.1853 0.023 Uiso 1 1 calc R
C11 C 0.14574(12) 0.45950(18) -0.08454(10) 0.0227(4) Uani 1 1 d .
H11 H 0.1193 0.4535 -0.1403 0.027 Uiso 1 1 calc R
C19 C 0.35796(12) 0.25618(17) 0.22442(10) 0.0211(4) Uani 1 1 d .
H19A H 0.3705 0.2436 0.1782 0.025 Uiso 1 1 calc R
H19B H 0.4089 0.2265 0.2715 0.025 Uiso 1 1 calc R
C2 C 0.24732(12) 0.61768(19) 0.44552(9) 0.0223(4) Uani 1 1 d .
H2 H 0.1972 0.6741 0.4189 0.027 Uiso 1 1 calc R
C15 C 0.19211(12) 0.79564(17) 0.26349(9) 0.0210(4) Uani 1 1 d .
H15A H 0.1987 0.8211 0.3171 0.025 Uiso 1 1 calc R
H15B H 0.2442 0.8276 0.2598 0.025 Uiso 1 1 calc R
C3 C 0.28424(12) 0.60275(19) 0.52742(10) 0.0239(4) Uani 1 1 d .
H3 H 0.2584 0.6506 0.5566 0.029 Uiso 1 1 calc R
C9 C 0.27087(13) 0.40308(19) 0.03972(10) 0.0244(4) Uani 1 1 d .
H9 H 0.3259 0.3631 0.0667 0.029 Uiso 1 1 calc R
C22 C 0.40411(13) 0.71643(18) 0.24873(11) 0.0280(5) Uani 1 1 d .
H22A H 0.3528 0.7544 0.2057 0.042 Uiso 1 1 calc R
H22B H 0.4527 0.7727 0.2502 0.042 Uiso 1 1 calc R
H22C H 0.4000 0.7294 0.2987 0.042 Uiso 1 1 calc R
C16 C 0.11829(13) 0.89106(18) 0.20393(10) 0.0265(4) Uani 1 1 d .
H16A H 0.1179 0.8841 0.1518 0.040 Uiso 1 1 calc R
H16B H 0.1254 0.9965 0.2210 0.040 Uiso 1 1 calc R
H16C H 0.0650 0.8527 0.2014 0.040 Uiso 1 1 calc R
C14 C 0.12353(12) 0.58750(17) 0.10032(9) 0.0191(4) Uani 1 1 d .
H14 H 0.0723 0.6363 0.0916 0.023 Uiso 1 1 calc R
C17 C 0.10084(12) 0.53486(18) 0.25489(9) 0.0208(4) Uani 1 1 d .
H17A H 0.0964 0.5671 0.3034 0.025 Uiso 1 1 calc R
H17B H 0.0510 0.5745 0.2096 0.025 Uiso 1 1 calc R
C10 C 0.22906(13) 0.39991(19) -0.04213(10) 0.0256(4) Uani 1 1 d .
H10 H 0.2567 0.3568 -0.0709 0.031 Uiso 1 1 calc R
C4 C 0.36014(12) 0.51728(18) 0.56904(10) 0.0236(4) Uani 1 1 d .
H4 H 0.3832 0.5104 0.6247 0.028 Uiso 1 1 calc R
C13 C 0.14528(12) 0.53127(16) 0.04014(9) 0.0174(4) Uani 1 1 d .
C5 C 0.39991(13) 0.44508(18) 0.52899(10) 0.0231(4) Uani 1 1 d .
H5 H 0.4496 0.3880 0.5564 0.028 Uiso 1 1 calc R
C1 C 0.28834(12) 0.54418(17) 0.40332(9) 0.0177(4) Uani 1 1 d .
C12 C 0.10351(12) 0.52573(17) -0.04482(9) 0.0204(4) Uani 1 1 d .
H12 H 0.0487 0.5662 -0.0727 0.025 Uiso 1 1 calc R
C6 C 0.36376(12) 0.45895(17) 0.44422(9) 0.0193(4) Uani 1 1 d .
C8 C 0.22766(12) 0.46899(16) 0.08164(9) 0.0176(4) Uani 1 1 d .
N3 N 0.18715(9) 0.56037(14) 0.17143(8) 0.0158(3) Uani 1 1 d .
N4 N 0.25229(9) 0.48659(14) 0.16249(7) 0.0170(3) Uani 1 1 d .
N1 N 0.26755(9) 0.54011(14) 0.32301(7) 0.0164(3) Uani 1 1 d .
N2 N 0.32855(9) 0.45520(13) 0.31335(8) 0.0172(3) Uani 1 1 d .
C24 C 0.03424(13) 0.14161(19) 0.03065(10) 0.0265(5) Uani 1 1 d .
H24 H 0.0573 0.2372 0.0514 0.032 Uiso 1 1 calc R
C23 C -0.03296(13) 0.0837(2) 0.04369(11) 0.0291(5) Uani 1 1 d .
H23 H -0.0553 0.1403 0.0732 0.035 Uiso 1 1 calc R
C25 C 0.06742(13) 0.0586(2) -0.01302(11) 0.0293(5) Uani 1 1 d .
H25 H 0.1128 0.0978 -0.0219 0.035 Uiso 1 1 calc R
C27 C 0.47292(13) 0.00003(19) 0.41791(10) 0.0306(5) Uani 1 1 d .
H27 H 0.4545 -0.0002 0.3626 0.037 Uiso 1 1 calc R
C28 C 0.54463(14) 0.08215(19) 0.46608(11) 0.0286(5) Uani 1 1 d .
H28 H 0.5748 0.1377 0.4434 0.034 Uiso 1 1 calc R
C26 C 0.42829(13) -0.0819(2) 0.45177(11) 0.0296(5) Uani 1 1 d .
H26 H 0.3797 -0.1373 0.4191 0.036 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'
B B 0.0013 0.0007 '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'
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_3
N1 B1 N3 106.17(13) .
N1 B1 C17 109.80(13) .
N3 B1 C17 106.51(13) .
N1 B1 C15 107.58(13) .
N3 B1 C15 110.30(12) .
C17 B1 C15 116.07(15) .
N4 B2 N2 106.29(14) .
N4 B2 C21 109.80(13) .
N2 B2 C21 108.84(13) .
N4 B2 C19 110.79(13) .
N2 B2 C19 107.14(12) .
C21 B2 C19 113.66(15) .
N2 C7 C6 109.29(16) .
C22 C21 B2 116.03(15) .
C12 C11 C10 120.68(16) .
C20 C19 B2 115.85(15) .
C3 C2 C1 117.29(17) .
C16 C15 B1 117.49(14) .
C2 C3 C4 122.31(17) .
C10 C9 C8 117.51(18) .
N3 C14 C13 109.45(16) .
C18 C17 B1 115.17(14) .
C9 C10 C11 122.51(17) .
C5 C4 C3 120.94(15) .
C14 C13 C8 104.71(14) .
C14 C13 C12 134.77(17) .
C8 C13 C12 120.52(15) .
C4 C5 C6 118.25(17) .
N1 C1 C6 108.79(15) .
N1 C1 C2 130.44(15) .
C6 C1 C2 120.77(15) .
C11 C12 C13 118.17(17) .
C7 C6 C1 104.67(14) .
C7 C6 C5 134.88(17) .
C1 C6 C5 120.44(16) .
N4 C8 C13 108.72(14) .
N4 C8 C9 130.68(16) .
C13 C8 C9 120.60(15) .
C14 N3 N4 109.99(13) .
C14 N3 B1 123.11(15) .
N4 N3 B1 126.90(13) .
N3 N4 C8 107.13(13) .
N3 N4 B2 125.82(12) .
C8 N4 B2 127.03(14) .
N2 N1 C1 107.26(13) .
N2 N1 B1 126.27(12) .
C1 N1 B1 126.36(14) .
C7 N2 N1 109.98(13) .
C7 N2 B2 123.21(15) .
N1 N2 B2 126.22(13) .
C25 C24 C23 120.18(17) .
C24 C23 C25 120.17(18) 3
C24 C25 C23 119.66(19) 3
C28 C27 C26 119.88(17) .
C27 C28 C26 119.81(18) 3_656
C27 C26 C28 120.31(18) 3_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 N1 1.576(2) .
B1 N3 1.601(2) .
B1 C17 1.602(3) .
B1 C15 1.611(2) .
C18 C17 1.529(2) .
C20 C19 1.517(2) .
B2 N4 1.571(2) .
B2 N2 1.594(2) .
B2 C21 1.599(3) .
B2 C19 1.611(2) .
C7 N2 1.327(2) .
C7 C6 1.397(2) .
C21 C22 1.519(2) .
C11 C12 1.361(2) .
C11 C10 1.409(3) .
C2 C3 1.371(2) .
C2 C1 1.408(2) .
C15 C16 1.523(2) .
C3 C4 1.413(3) .
C9 C10 1.366(2) .
C9 C8 1.404(2) .
C14 N3 1.322(2) .
C14 C13 1.402(2) .
C4 C5 1.357(2) .
C13 C8 1.403(2) .
C13 C12 1.418(2) .
C5 C6 1.419(2) .
C1 N1 1.3665(19) .
C1 C6 1.404(2) .
C8 N4 1.3724(19) .
N3 N4 1.3631(19) .
N1 N2 1.3574(19) .
C24 C25 1.374(3) .
C24 C23 1.375(3) .
C23 C25 1.384(3) 3
C25 C23 1.384(3) 3
C27 C28 1.374(3) .
C27 C26 1.378(3) .
C28 C26 1.381(3) 3_656
C26 C28 1.381(3) 3_656
