#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/79/1517918.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_1517918
loop_
_publ_author_name
'Sun, Feiye'
'Lv, Lily'
'Huang, Min'
'Zhou, Zhaohui'
'Fang, Xiangdong'
_publ_section_title
;
 Palladium-catalyzed cross-coupling reactions of 4a,8a-azaboranaphthalene.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5024
_journal_page_last               5027
_journal_paper_doi               10.1021/ol502339h
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H7 B I N'
_chemical_formula_sum            'C8 H7 B I N'
_chemical_formula_weight         254.86
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2013-07-20
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.147(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4427(2)
_cell_length_b                   11.8161(4)
_cell_length_c                   16.0682(5)
_cell_measurement_temperature    173(2)
_cell_volume                     838.66(5)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6249
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  0.5213
_exptl_absorpt_correction_T_min  0.2560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.704
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0242
_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)+(0.0225P)²+1.1093P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0579
_reflns_number_gt                1754
_reflns_number_total             1876
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502339h_si_006.cif
_cod_data_source_block           sad
_cod_database_code               1517918
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
I1 I 0.20713(4) 0.745997(15) 0.043110(11) 0.02681(8) Uani 1 1 d .
N2 N 0.1830(5) 0.52513(19) 0.26774(14) 0.0206(5) Uani 1 1 d .
C3 C 0.1062(6) 0.6200(2) 0.12828(16) 0.0197(5) Uani 1 1 d .
C4 C -0.1046(6) 0.5407(2) 0.10237(17) 0.0233(6) Uani 1 1 d .
H4 H -0.2068 0.5434 0.0474 0.028 Uiso 1 1 calc R
B5 B 0.2707(6) 0.6180(3) 0.21623(18) 0.0186(6) Uani 1 1 d .
C6 C 0.3187(7) 0.5125(3) 0.34965(17) 0.0261(6) Uani 1 1 d .
H6 H 0.2604 0.4510 0.3825 0.031 Uiso 1 1 calc R
C7 C 0.5080(6) 0.6981(2) 0.25719(17) 0.0222(5) Uani 1 1 d .
H7 H 0.5730 0.7611 0.2270 0.027 Uiso 1 1 calc R
C8 C -0.0330(6) 0.4468(2) 0.23801(19) 0.0247(6) Uani 1 1 d .
H8 H -0.0857 0.3876 0.2737 0.030 Uiso 1 1 calc R
C9 C -0.1704(7) 0.4531(2) 0.15908(19) 0.0272(6) Uani 1 1 d .
H9 H -0.3162 0.3973 0.1405 0.033 Uiso 1 1 calc R
C10 C 0.5298(7) 0.5855(3) 0.38297(18) 0.0287(6) Uani 1 1 d .
H10 H 0.6170 0.5741 0.4389 0.034 Uiso 1 1 calc R
C11 C 0.6273(6) 0.6792(2) 0.33735(18) 0.0268(6) Uani 1 1 d .
H11 H 0.7772 0.7290 0.3631 0.032 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.03069(13) 0.02690(13) 0.02252(12) 0.00425(7) 0.00141(8) -0.00301(7)
N2 0.0210(11) 0.0204(11) 0.0212(11) 0.0001(9) 0.0059(9) 0.0044(9)
C3 0.0208(12) 0.0199(13) 0.0190(12) 0.0005(10) 0.0055(10) 0.0018(10)
C4 0.0218(13) 0.0267(14) 0.0218(13) -0.0039(11) 0.0043(11) 0.0002(11)
B5 0.0192(14) 0.0181(14) 0.0194(14) -0.0024(11) 0.0060(11) 0.0042(11)
C6 0.0290(15) 0.0283(15) 0.0223(13) 0.0067(11) 0.0083(11) 0.0092(12)
C7 0.0230(13) 0.0192(13) 0.0246(13) -0.0013(11) 0.0039(11) 0.0018(10)
C8 0.0240(14) 0.0177(13) 0.0340(16) 0.0019(11) 0.0110(12) 0.0004(10)
C9 0.0240(14) 0.0226(14) 0.0364(17) -0.0079(12) 0.0088(12) -0.0057(11)
C10 0.0325(15) 0.0356(17) 0.0178(13) 0.0007(11) 0.0012(11) 0.0103(13)
C11 0.0261(14) 0.0268(15) 0.0266(14) -0.0067(12) -0.0013(12) 0.0036(12)
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'
I I -0.4742 1.8119 '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
C6 N2 B5 120.2(2)
C8 N2 B5 121.9(2)
C8 N2 C6 118.0(2)
C4 C3 I1 118.5(2)
C4 C3 B5 121.4(2)
B5 C3 I1 120.08(19)
C3 C4 C9 119.0(3)
N2 B5 C3 114.2(2)
N2 B5 C7 116.2(2)
C7 B5 C3 129.6(3)
C10 C6 N2 121.4(3)
C11 C7 B5 119.5(3)
C9 C8 N2 121.1(3)
C8 C9 C4 122.4(3)
C6 C10 C11 122.2(3)
C7 C11 C10 120.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C3 2.103(3)
N2 B5 1.453(4)
N2 C6 1.396(3)
N2 C8 1.381(4)
C3 C4 1.358(4)
C3 B5 1.520(4)
C4 C9 1.430(4)
B5 C7 1.514(4)
C6 C10 1.342(4)
C7 C11 1.358(4)
C8 C9 1.349(4)
C10 C11 1.421(4)
