#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/79/1517921.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_1517921
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_sum            'C8 H14 B N O'
_chemical_formula_weight         151.01
_chemical_name_common            'Boron nitrogen hydroxide'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.816(1)
_cell_length_b                   7.3282(6)
_cell_length_c                   17.716(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1663.9(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Oxford Gemini Diffractometer'
_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  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5471
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9627
_exptl_absorpt_process_details   2theta
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0519
_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)+(0.0420P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1074
_reflns_number_gt                2152
_reflns_number_total             2613
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502339h_si_004.cif
_cod_data_source_block           sad
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_sg_symbol_H-M      Pca21
_cod_database_code               1517921
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, 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
O1 O 0.30025(15) -0.8452(3) 0.76460(13) 0.0272(5) Uani 1 1 d D
O2 O 0.45390(15) -0.3507(3) 0.77867(14) 0.0285(5) Uani 1 1 d D
N1 N 0.42323(15) -0.6612(3) 0.68691(15) 0.0203(5) Uani 1 1 d .
H1C H 0.4122 -0.5614 0.7183 0.024 Uiso 1 1 calc R
N2 N 0.33350(15) -0.1569(3) 0.85452(15) 0.0223(6) Uani 1 1 d .
H2B H 0.3476 -0.0597 0.8224 0.027 Uiso 1 1 calc R
B1 B 0.3155(2) -0.7818(4) 0.6866(2) 0.0212(7) Uani 1 1 d .
B2 B 0.4385(2) -0.2865(4) 0.8564(2) 0.0206(7) Uani 1 1 d .
C1 C 0.2256(2) -0.6458(4) 0.65716(19) 0.0266(7) Uani 1 1 d .
H1A H 0.1666 -0.7194 0.6378 0.032 Uiso 1 1 calc R
H1B H 0.1996 -0.5733 0.7004 0.032 Uiso 1 1 calc R
C2 C 0.2608(3) -0.5185(4) 0.5966(3) 0.0325(11) Uani 1 1 d .
H2A H 0.2092 -0.4501 0.5705 0.039 Uiso 1 1 calc R
C3 C 0.3585(2) -0.4954(4) 0.5772(3) 0.0291(11) Uani 1 1 d .
H3A H 0.3721 -0.4103 0.5380 0.035 Uiso 1 1 calc R
C4 C 0.4493(2) -0.5889(4) 0.61048(19) 0.0253(7) Uani 1 1 d .
H4A H 0.5084 -0.5023 0.6145 0.030 Uiso 1 1 calc R
H4B H 0.4710 -0.6907 0.5773 0.030 Uiso 1 1 calc R
C5 C 0.51239(19) -0.7664(4) 0.7188(2) 0.0263(7) Uani 1 1 d .
H5A H 0.5021 -0.7816 0.7738 0.032 Uiso 1 1 calc R
H5B H 0.5777 -0.6967 0.7110 0.032 Uiso 1 1 calc R
C6 C 0.5229(2) -0.9500(4) 0.6829(2) 0.0277(7) Uani 1 1 d .
H6A H 0.5882 -1.0107 0.6871 0.033 Uiso 1 1 calc R
C7 C 0.4479(2) -1.0330(5) 0.6460(2) 0.0254(8) Uani 1 1 d .
H7A H 0.4622 -1.1505 0.6258 0.030 Uiso 1 1 calc R
C8 C 0.3404(2) -0.9547(4) 0.6334(2) 0.0256(7) Uani 1 1 d .
H8A H 0.2878 -1.0509 0.6430 0.031 Uiso 1 1 calc R
H8B H 0.3338 -0.9172 0.5799 0.031 Uiso 1 1 calc R
C9 C 0.40891(19) -0.4568(4) 0.9097(2) 0.0230(7) Uani 1 1 d .
H9A H 0.4581 -0.5579 0.8994 0.028 Uiso 1 1 calc R
H9B H 0.4183 -0.4201 0.9631 0.028 Uiso 1 1 calc R
C10 C 0.2990(2) -0.5260(4) 0.8993(2) 0.0262(9) Uani 1 1 d .
H10A H 0.2805 -0.6389 0.9221 0.031 Uiso 1 1 calc R
C11 C 0.2267(2) -0.4378(4) 0.8602(2) 0.0274(7) Uani 1 1 d .
H11A H 0.1600 -0.4935 0.8557 0.033 Uiso 1 1 calc R
C12 C 0.2424(2) -0.2567(4) 0.8225(2) 0.0274(7) Uani 1 1 d .
H12A H 0.2534 -0.2759 0.7678 0.033 Uiso 1 1 calc R
H12B H 0.1787 -0.1818 0.8289 0.033 Uiso 1 1 calc R
C13 C 0.3077(2) -0.0783(4) 0.92987(19) 0.0254(7) Uani 1 1 d .
H13A H 0.2818 -0.1766 0.9633 0.030 Uiso 1 1 calc R
H13B H 0.2511 0.0126 0.9240 0.030 Uiso 1 1 calc R
C14 C 0.4012(3) 0.0127(4) 0.9665(3) 0.0342(12) Uani 1 1 d .
H14A H 0.3892 0.0966 1.0064 0.041 Uiso 1 1 calc R
C15 C 0.4992(3) -0.0191(4) 0.9454(3) 0.0297(10) Uani 1 1 d .
H15A H 0.5527 0.0496 0.9693 0.036 Uiso 1 1 calc R
C16 C 0.5313(2) -0.1549(4) 0.88703(19) 0.0263(7) Uani 1 1 d .
H16A H 0.5872 -0.2324 0.9084 0.032 Uiso 1 1 calc R
H16B H 0.5612 -0.0881 0.8435 0.032 Uiso 1 1 calc R
H2 H 0.474(2) -0.261(4) 0.753(2) 0.048(11) Uiso 1 1 d D
H1 H 0.278(3) -0.762(4) 0.793(2) 0.067(14) Uiso 1 1 d D
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C4 110.9(2)
C5 N1 B1 111.6(2)
C4 N1 B1 112.2(2)
C12 N2 C13 110.9(2)
C12 N2 B2 111.4(2)
C13 N2 B2 112.7(2)
O1 B1 C1 113.9(2)
O1 B1 C8 109.1(3)
C1 B1 C8 116.0(3)
O1 B1 N1 106.2(2)
C1 B1 N1 105.7(2)
C8 B1 N1 105.0(2)
O2 B2 C9 109.5(3)
O2 B2 C16 113.9(2)
C9 B2 C16 115.8(3)
O2 B2 N2 106.0(2)
C9 B2 N2 105.4(2)
C16 B2 N2 105.2(2)
C2 C1 B1 113.8(2)
C3 C2 C1 124.0(3)
C2 C3 C4 126.2(4)
C3 C4 N1 110.6(3)
N1 C5 C6 112.0(2)
C7 C6 C5 124.2(2)
C6 C7 C8 124.5(3)
C7 C8 B1 113.2(3)
C10 C9 B2 114.1(3)
C11 C10 C9 123.5(3)
C10 C11 C12 124.8(2)
N2 C12 C11 111.7(2)
N2 C13 C14 112.2(3)
C15 C14 C13 123.3(4)
C14 C15 C16 124.8(3)
C15 C16 B2 115.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 B1 1.471(4)
O2 B2 1.468(4)
N1 C5 1.489(3)
N1 C4 1.492(4)
N1 B1 1.639(3)
N2 C12 1.490(3)
N2 C13 1.491(4)
N2 B2 1.647(3)
B1 C1 1.611(4)
B1 C8 1.611(5)
B2 C9 1.611(5)
B2 C16 1.625(4)
C1 C2 1.492(5)
C2 C3 1.310(6)
C3 C4 1.473(5)
C5 C6 1.495(4)
C6 C7 1.313(5)
C7 C8 1.509(4)
C9 C10 1.509(4)
C10 C11 1.325(5)
C11 C12 1.499(4)
C13 C14 1.517(5)
C14 C15 1.330(6)
C15 C16 1.493(5)
