#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/87/2018780.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018780
loop_
_publ_author_name
'Sarina, Evan A.'
'Olmstead, Marilyn M.'
'Nguyen, Dung N.'
'Groziak, Michael P.'
_publ_section_title
;
 1-Hydroxy-1H-benzo[d][1,2,6]oxazaborinin-4(3H)-one
;
_journal_coeditor_code           FA3302
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              183
_journal_page_last               185
_journal_paper_doi               10.1107/S0108270113000681
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C7 H6 B N O3'
_chemical_formula_moiety         'C7 H6 B N O3'
_chemical_formula_sum            'C7 H6 B N O3'
_chemical_formula_weight         162.94
_chemical_name_common
;
1-Hydroxy-1,3-dihydro-2,3,1-benzoxazaborinin-4-one
;
_chemical_name_systematic
;
1-Hydroxy-1H-benzo[d][1,2,6]oxazaborinin-4(3H)-one
;
_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                 107.792(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0848(3)
_cell_length_b                   6.2043(2)
_cell_length_c                   13.1207(5)
_cell_measurement_reflns_used    8670
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      32.89
_cell_measurement_theta_min      3.26
_cell_volume                     704.17(4)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       ω
_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  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11658
_diffrn_reflns_theta_full        32.00
_diffrn_reflns_theta_max         33.07
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.537
_refine_diff_density_min         -0.235
_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     117
_refine_ls_number_reflns         2564
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0336
_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)+(0.0626P)²+0.1884P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                2420
_reflns_number_total             2564
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3302.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018780
_cod_database_fobs_code          2018780
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 0.40195(6) -0.00533(8) 0.20721(4) 0.01483(12) Uani d . 1 1
O O2 0.40143(6) -0.24104(8) 0.45339(4) 0.01368(12) Uani d . 1 1
O O3 0.26801(6) -0.16815(9) 0.57746(4) 0.01599(12) Uani d . 1 1
H H3 0.316(2) -0.283(3) 0.6146(14) 0.049(4) Uiso d . 1 1
N N1 0.42848(7) -0.19124(10) 0.35710(5) 0.01385(13) Uani d . 1 1
H H1 0.4867(16) -0.292(2) 0.3376(11) 0.030(3) Uiso d . 1 1
C C1 0.22797(7) 0.08701(11) 0.41957(5) 0.01179(13) Uani d . 1 1
C C2 0.12594(8) 0.22893(12) 0.44704(5) 0.01483(14) Uani d . 1 1
H H2 0.0931 0.1998 0.5078 0.018 Uiso calc R 1 1
C C3 0.07270(9) 0.41218(12) 0.38565(6) 0.01623(14) Uani d . 1 1
H H3A 0.0026 0.5067 0.4042 0.019 Uiso calc R 1 1
C C4 0.12176(8) 0.45789(12) 0.29689(6) 0.01533(14) Uani d . 1 1
H H4 0.0870 0.5853 0.2566 0.018 Uiso calc R 1 1
C C5 0.22112(8) 0.31811(11) 0.26719(5) 0.01364(13) Uani d . 1 1
H H5 0.2536 0.3480 0.2063 0.016 Uiso calc R 1 1
C C6 0.27254(7) 0.13246(11) 0.32847(5) 0.01141(13) Uani d . 1 1
C C7 0.37126(7) -0.02250(11) 0.29437(5) 0.01168(13) Uani d . 1 1
B B1 0.29826(9) -0.11392(12) 0.48663(6) 0.01219(14) Uani d . 1 1
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
B1 O2 N1 118.70(5)
B1 O3 H3 118.9(11)
C7 N1 O2 126.12(6)
C7 N1 H1 121.2(9)
O2 N1 H1 112.6(9)
C6 C1 C2 118.56(6)
C6 C1 B1 118.05(6)
C2 C1 B1 123.37(6)
C3 C2 C1 120.27(6)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 120.34(6)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
C5 C4 C3 120.44(6)
C5 C4 H4 119.8
C3 C4 H4 119.8
C4 C5 C6 118.89(6)
C4 C5 H5 120.6
C6 C5 H5 120.6
C5 C6 C1 121.46(6)
C5 C6 C7 119.28(6)
C1 C6 C7 119.22(6)
O1 C7 N1 118.21(6)
O1 C7 C6 122.92(6)
N1 C7 C6 118.85(6)
O3 B1 O2 118.36(6)
O3 B1 C1 123.02(6)
O2 B1 C1 118.59(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2616(8)
O2 B1 1.3930(9)
O2 N1 1.3935(7)
O3 B1 1.3449(8)
O3 H3 0.898(18)
N1 C7 1.3350(9)
N1 H1 0.905(15)
C1 C6 1.4029(9)
C1 C2 1.4031(9)
C1 B1 1.5468(10)
C2 C3 1.3918(10)
C2 H2 0.9500
C3 C4 1.3974(10)
C3 H3A 0.9500
C4 C5 1.3906(10)
C4 H4 0.9500
C5 C6 1.4008(9)
C5 H5 0.9500
C6 C7 1.4745(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 4_556 0.898(18) 1.797(18) 2.6864(7) 170.4(16)
N1 H1 O1 2_645 0.905(15) 1.866(15) 2.7707(8) 177.2(13)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
B1 O2 N1 C7 4.21(10)
C6 C1 C2 C3 -0.99(10)
B1 C1 C2 C3 177.02(7)
C1 C2 C3 C4 -0.77(11)
C2 C3 C4 C5 1.68(11)
C3 C4 C5 C6 -0.78(10)
C4 C5 C6 C1 -1.02(10)
C4 C5 C6 C7 176.79(6)
C2 C1 C6 C5 1.90(10)
B1 C1 C6 C5 -176.22(6)
C2 C1 C6 C7 -175.92(6)
B1 C1 C6 C7 5.97(9)
O2 N1 C7 O1 -177.11(6)
O2 N1 C7 C6 1.54(10)
C5 C6 C7 O1 -5.99(10)
C1 C6 C7 O1 171.87(6)
C5 C6 C7 N1 175.42(6)
C1 C6 C7 N1 -6.71(9)
N1 O2 B1 O3 177.37(6)
N1 O2 B1 C1 -4.60(9)
C6 C1 B1 O3 177.52(6)
C2 C1 B1 O3 -0.50(11)
C6 C1 B1 O2 -0.41(10)
C2 C1 B1 O2 -178.43(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654414
