#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029880.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_4029880
loop_
_publ_author_name
'Molander, Gary A.'
'Wisniewski, Steven R.'
_publ_section_title
;
 Accessing 2,1-Borazaronaphthols: Self-Arylation of
 1-Alkyl-2-aryl-3-bromo-2,1-borazaronaphthalenes.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8339
_journal_page_last               8347
_journal_paper_doi               10.1021/jo501638q
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C27 H22 B N O'
_chemical_formula_weight         387.27
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.043(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.4000(16)
_cell_length_b                   5.6484(3)
_cell_length_c                   23.9962(15)
_cell_measurement_temperature    100(1)
_cell_volume                     3954.8(4)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            43446
_diffrn_reflns_theta_full        25.39
_diffrn_reflns_theta_max         25.39
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0360
_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)+(0.0470P)²+3.7963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                3168
_reflns_number_total             3631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501638q_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

 Adding full bibliography for 4029880--4029881.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c      '
_cod_database_code               4029880
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
C1 C 0.60187(4) 0.1613(2) 0.15601(5) 0.0186(3) Uani 1 1 d .
C2 C 0.63780(4) -0.0026(2) 0.16401(5) 0.0204(3) Uani 1 1 d .
H2 H 0.6396 -0.1220 0.1377 0.027 Uiso 1 1 calc R
C3 C 0.67056(4) 0.0100(2) 0.21018(5) 0.0197(3) Uani 1 1 d .
H3 H 0.6941 -0.1008 0.2140 0.026 Uiso 1 1 calc R
C4 C 0.66948(4) 0.1849(2) 0.25166(5) 0.0174(3) Uani 1 1 d .
C5 C 0.63258(4) 0.3404(2) 0.24475(5) 0.0185(3) Uani 1 1 d .
H5 H 0.6302 0.4544 0.2722 0.025 Uiso 1 1 calc R
C6 C 0.59881(4) 0.3333(2) 0.19830(5) 0.0184(3) Uani 1 1 d .
C7 C 0.56035(4) 0.4933(2) 0.19461(5) 0.0201(3) Uani 1 1 d .
H7 H 0.5581 0.5966 0.2243 0.027 Uiso 1 1 calc R
C8 C 0.52739(4) 0.5004(2) 0.14994(5) 0.0208(3) Uani 1 1 d .
C9 C 0.57332(4) -0.0177(2) 0.06495(5) 0.0218(3) Uani 1 1 d .
H9a H 0.5451 -0.0174 0.0394 0.029 Uiso 1 1 calc R
H9b H 0.5758 -0.1710 0.0833 0.029 Uiso 1 1 calc R
C10 C 0.61308(4) 0.0099(2) 0.03090(5) 0.0199(3) Uani 1 1 d .
C11 C 0.62162(5) -0.1721(2) -0.00558(5) 0.0226(3) Uani 1 1 d .
H11 H 0.6028 -0.3049 -0.0087 0.030 Uiso 1 1 calc R
C12 C 0.65774(5) -0.1579(3) -0.03728(5) 0.0253(3) Uani 1 1 d .
H12 H 0.6629 -0.2802 -0.0617 0.034 Uiso 1 1 calc R
C13 C 0.68624(5) 0.0383(3) -0.03278(6) 0.0266(3) Uani 1 1 d .
H13 H 0.7108 0.0470 -0.0537 0.035 Uiso 1 1 calc R
C14 C 0.67804(5) 0.2208(3) 0.00300(6) 0.0247(3) Uani 1 1 d .
H14 H 0.6970 0.3533 0.0060 0.033 Uiso 1 1 calc R
C15 C 0.64145(4) 0.2068(2) 0.03460(5) 0.0217(3) Uani 1 1 d .
H15 H 0.6360 0.3307 0.0584 0.029 Uiso 1 1 calc R
C16 C 0.70581(4) 0.1997(2) 0.30058(5) 0.0182(3) Uani 1 1 d .
C17 C 0.73785(4) 0.0187(2) 0.31265(5) 0.0215(3) Uani 1 1 d .
H17 H 0.7365 -0.1143 0.2897 0.029 Uiso 1 1 calc R
C18 C 0.77171(5) 0.0329(2) 0.35822(6) 0.0234(3) Uani 1 1 d .
H18 H 0.7928 -0.0894 0.3651 0.031 Uiso 1 1 calc R
C19 C 0.77426(4) 0.2274(2) 0.39343(5) 0.0226(3) Uani 1 1 d .
H19 H 0.7965 0.2354 0.4244 0.030 Uiso 1 1 calc R
C20 C 0.74311(4) 0.4102(3) 0.38185(5) 0.0230(3) Uani 1 1 d .
H20 H 0.7446 0.5425 0.4051 0.031 Uiso 1 1 calc R
C21 C 0.70968(4) 0.3976(2) 0.33588(5) 0.0208(3) Uani 1 1 d .
H21 H 0.6894 0.5232 0.3284 0.028 Uiso 1 1 calc R
C22 C 0.48696(4) 0.6575(2) 0.15049(5) 0.0207(3) Uani 1 1 d .
C23 C 0.49035(4) 0.8766(2) 0.17771(5) 0.0225(3) Uani 1 1 d .
H23 H 0.5189 0.9306 0.1938 0.030 Uiso 1 1 calc R
C24 C 0.45190(5) 1.0145(3) 0.18111(6) 0.0264(3) Uani 1 1 d .
H24 H 0.4547 1.1584 0.2001 0.035 Uiso 1 1 calc R
C25 C 0.40920(5) 0.9396(3) 0.15643(6) 0.0270(3) Uani 1 1 d .
H25 H 0.3834 1.0325 0.1588 0.036 Uiso 1 1 calc R
C26 C 0.40531(5) 0.7250(3) 0.12829(6) 0.0257(3) Uani 1 1 d .
H26 H 0.3768 0.6748 0.1112 0.034 Uiso 1 1 calc R
C27 C 0.44362(4) 0.5850(3) 0.12549(5) 0.0234(3) Uani 1 1 d .
H27 H 0.4405 0.4407 0.1067 0.031 Uiso 1 1 calc R
B1 B 0.53390(5) 0.3363(3) 0.10002(6) 0.0227(3) Uani 1 1 d .
N1 N 0.56997(4) 0.1645(2) 0.10779(4) 0.0207(2) Uani 1 1 d .
O1 O 0.50893(3) 0.34444(19) 0.04757(4) 0.0302(2) Uani 1 1 d .
H1 H 0.4917 0.4593 0.0457 0.045 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'
O O 0.0106 0.0060 '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
N1 C1 C2 122.72(11)
N1 C1 C6 119.32(11)
C2 C1 C6 117.94(11)
C3 C2 C1 121.17(12)
C2 C3 C4 122.11(12)
C5 C4 C3 116.41(11)
C5 C4 C16 122.16(11)
C3 C4 C16 121.43(11)
C4 C5 C6 122.95(12)
C5 C6 C1 119.31(11)
C5 C6 C7 120.36(11)
C1 C6 C7 120.29(11)
C8 C7 C6 123.14(12)
C7 C8 C22 120.43(12)
C7 C8 B1 116.82(12)
C22 C8 B1 122.75(11)
N1 C9 C10 115.38(11)
C15 C10 C11 118.61(12)
C15 C10 C9 123.11(12)
C11 C10 C9 118.28(12)
C12 C11 C10 120.85(13)
C11 C12 C13 120.13(13)
C14 C13 C12 119.68(13)
C13 C14 C15 120.09(13)
C10 C15 C14 120.64(12)
C17 C16 C21 117.18(12)
C17 C16 C4 121.51(12)
C21 C16 C4 121.30(11)
C18 C17 C16 121.45(12)
C19 C18 C17 120.49(12)
C18 C19 C20 119.00(12)
C19 C20 C21 120.52(13)
C20 C21 C16 121.34(12)
C23 C22 C27 117.91(12)
C23 C22 C8 121.48(12)
C27 C22 C8 120.56(12)
C24 C23 C22 120.93(12)
C23 C24 C25 120.43(13)
C26 C25 C24 119.43(12)
C27 C26 C25 120.30(13)
C26 C27 C22 120.96(13)
O1 B1 N1 116.40(12)
O1 B1 C8 125.82(12)
N1 B1 C8 117.75(12)
C1 N1 B1 121.82(11)
C1 N1 C9 118.39(10)
B1 N1 C9 119.77(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3975(16)
C1 C2 1.3999(18)
C1 C6 1.4158(18)
C2 C3 1.3778(18)
C3 C4 1.4055(18)
C4 C5 1.3901(18)
C4 C16 1.4893(17)
C5 C6 1.3994(18)
C6 C7 1.4416(18)
C7 C8 1.3547(18)
C8 C22 1.4848(18)
C8 B1 1.545(2)
C9 N1 1.4665(16)
C9 C10 1.5142(18)
C10 C15 1.3867(19)
C10 C11 1.3929(18)
C11 C12 1.3822(19)
C12 C13 1.385(2)
C13 C14 1.382(2)
C14 C15 1.3922(19)
C16 C17 1.3963(18)
C16 C21 1.3985(18)
C17 C18 1.3878(19)
C18 C19 1.382(2)
C19 C20 1.3856(19)
C20 C21 1.3865(18)
C22 C23 1.3975(19)
C22 C27 1.4013(19)
C23 C24 1.3835(19)
C24 C25 1.387(2)
C25 C26 1.385(2)
C26 C27 1.3846(19)
B1 O1 1.3779(17)
B1 N1 1.4325(19)
