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#$Date: 2022-03-10 11:59:27 +0200 (Thu, 10 Mar 2022) $
#$Revision: 273600 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104723.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_8104723
loop_
_publ_author_name
'Ren, Huaping'
'Miao, Zong-Cheng'
_publ_section_title
;
 The crystal structure of
 2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine,
 C17H13BN2O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              821
_journal_page_last               822
_journal_paper_doi               10.1515/ncrs-2021-0081
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C17 H13 B N2 O2'
_chemical_formula_sum            'C17 H13 B N2 O2'
_chemical_formula_weight         288.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.0820(14)
_cell_length_b                   13.1135(19)
_cell_length_c                   20.644(3)
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      60.46
_cell_measurement_theta_min      3.47
_cell_volume                     2729.3(7)
_computing_cell_refinement       'SAINT V8.38A '[1]'
_computing_data_reduction        'SAINT V8.38A '[1]'
_computing_molecular_graphics    'Olex2 '[2]'
_computing_publication_material  'Olex2 '[2]'
_computing_structure_refinement  'XL '[3]'
_computing_structure_solution    'SHELXT 2014/5 '[4]'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20002
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.639
_diffrn_reflns_theta_min         6.092
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1292 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.8545.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0046(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0470P)²+0.6607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2833
_reflns_number_total             3078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0081_suppl.cif
_cod_data_source_block           ok
_cod_database_code               8104723
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C16(H16), C1(H1A), C15(H15), C12(H12), C3(H3), C5(H5), C7(H7),
  C2(H2A), C6(H6)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10474(8) 0.25412(6) 0.61458(4) 0.0353(2) Uani 1 1 d . . . . .
O2 O 0.01125(8) 0.40691(7) 0.58396(4) 0.0434(2) Uani 1 1 d . . . . .
N1 N 0.48663(9) 0.45974(7) 0.39012(4) 0.0297(2) Uani 1 1 d . . . . .
H1 H 0.507478 0.394714 0.392771 0.036 Uiso 1 1 calc R U . . .
N2 N 0.34936(9) 0.60087(7) 0.42162(4) 0.0293(2) Uani 1 1 d . . . . .
H2 H 0.282731 0.625577 0.444242 0.035 Uiso 1 1 calc R U . . .
C1 C 0.38514(11) 0.76835(8) 0.37447(5) 0.0331(3) Uani 1 1 d . . . . .
H1A H 0.316883 0.796379 0.400727 0.040 Uiso 1 1 calc R U . . .
C2 C 0.45463(12) 0.83120(9) 0.33104(6) 0.0374(3) Uani 1 1 d . . . . .
H2A H 0.431688 0.901281 0.327802 0.045 Uiso 1 1 calc R U . . .
C3 C 0.55460(12) 0.79335(9) 0.29337(5) 0.0357(3) Uani 1 1 d . . . . .
H3 H 0.599634 0.837057 0.263987 0.043 Uiso 1 1 calc R U . . .
C4 C 0.59150(10) 0.68945(8) 0.29784(5) 0.0297(2) Uani 1 1 d . . . . .
C5 C 0.69781(11) 0.64768(9) 0.26189(5) 0.0350(3) Uani 1 1 d . . . . .
H5 H 0.747410 0.690028 0.233473 0.042 Uiso 1 1 calc R U . . .
C6 C 0.72969(11) 0.54681(9) 0.26776(6) 0.0385(3) Uani 1 1 d . . . . .
H6 H 0.800485 0.519766 0.242712 0.046 Uiso 1 1 calc R U . . .
C7 C 0.66001(11) 0.48241(9) 0.31001(5) 0.0347(3) Uani 1 1 d . . . . .
H7 H 0.683893 0.412531 0.313403 0.042 Uiso 1 1 calc R U . . .
C8 C 0.55694(10) 0.52042(8) 0.34659(5) 0.0272(2) Uani 1 1 d . . . . .
C9 C 0.52002(9) 0.62470(8) 0.34087(5) 0.0258(2) Uani 1 1 d . . . . .
C10 C 0.41567(10) 0.66627(8) 0.37910(5) 0.0270(2) Uani 1 1 d . . . . .
C11 C 0.31147(10) 0.42714(8) 0.48093(5) 0.0271(2) Uani 1 1 d . . . . .
C12 C 0.18969(10) 0.45790(8) 0.50846(5) 0.0318(2) Uani 1 1 d . . . . .
H12 H 0.149761 0.520874 0.496755 0.038 Uiso 1 1 calc R U . . .
C13 C 0.13074(10) 0.39425(8) 0.55256(5) 0.0312(2) Uani 1 1 d . . . . .
C14 C 0.18598(10) 0.30236(8) 0.57032(5) 0.0286(2) Uani 1 1 d . . . . .
C15 C 0.30347(10) 0.26872(8) 0.54486(5) 0.0304(2) Uani 1 1 d . . . . .
H15 H 0.341221 0.205130 0.556945 0.037 Uiso 1 1 calc R U . . .
C16 C 0.36486(10) 0.33351(8) 0.49995(5) 0.0286(2) Uani 1 1 d . . . . .
H16 H 0.446858 0.312706 0.481522 0.034 Uiso 1 1 calc R U . . .
C17 C 0.01058(11) 0.33085(10) 0.63350(6) 0.0383(3) Uani 1 1 d . . . . .
H17A H -0.079013 0.300699 0.637805 0.046 Uiso 1 1 calc R U . . .
H17B H 0.036120 0.361119 0.675619 0.046 Uiso 1 1 calc R U . . .
B1 B 0.38360(11) 0.49682(9) 0.43031(5) 0.0273(2) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0073 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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_1
_geom_angle_site_symmetry_3
C14 O1 C17 104.53(8) . .
C13 O2 C17 104.88(8) . .
C8 N1 H1 118.1 . .
C8 N1 B1 123.71(9) . .
B1 N1 H1 118.1 . .
C10 N2 H2 118.2 . .
C10 N2 B1 123.59(9) . .
B1 N2 H2 118.2 . .
C2 C1 H1A 119.9 . .
C10 C1 H1A 119.9 . .
C10 C1 C2 120.21(10) . .
C1 C2 H2A 119.4 . .
C3 C2 C1 121.19(10) . .
C3 C2 H2A 119.4 . .
C2 C3 H3 119.8 . .
C2 C3 C4 120.43(10) . .
C4 C3 H3 119.8 . .
C3 C4 C9 118.78(10) . .
C5 C4 C3 122.53(10) . .
C5 C4 C9 118.68(10) . .
C4 C5 H5 119.8 . .
C6 C5 C4 120.44(10) . .
C6 C5 H5 119.8 . .
C5 C6 H6 119.3 . .
C5 C6 C7 121.34(10) . .
C7 C6 H6 119.3 . .
C6 C7 H7 120.0 . .
C8 C7 C6 120.04(10) . .
C8 C7 H7 120.0 . .
N1 C8 C9 117.99(9) . .
C7 C8 N1 122.03(10) . .
C7 C8 C9 119.99(9) . .
C8 C9 C4 119.50(9) . .
C8 C9 C10 121.04(9) . .
C10 C9 C4 119.42(10) . .
N2 C10 C9 117.82(9) . .
C1 C10 N2 122.23(10) . .
C1 C10 C9 119.93(10) . .
C12 C11 B1 120.36(9) . .
C16 C11 C12 118.23(9) . .
C16 C11 B1 121.41(9) . .
C11 C12 H12 121.0 . .
C13 C12 C11 118.07(10) . .
C13 C12 H12 121.0 . .
C12 C13 O2 128.18(10) . .
C12 C13 C14 122.30(10) . .
C14 C13 O2 109.49(9) . .
C13 C14 O1 109.71(9) . .
C15 C14 O1 128.30(10) . .
C15 C14 C13 121.98(10) . .
C14 C15 H15 121.9 . .
C14 C15 C16 116.15(10) . .
C16 C15 H15 121.9 . .
C11 C16 C15 123.26(10) . .
C11 C16 H16 118.4 . .
C15 C16 H16 118.4 . .
O1 C17 H17A 110.3 . .
O1 C17 H17B 110.3 . .
O2 C17 O1 106.93(9) . .
O2 C17 H17A 110.3 . .
O2 C17 H17B 110.3 . .
H17A C17 H17B 108.6 . .
N1 B1 N2 115.77(9) . .
N1 B1 C11 122.08(10) . .
N2 B1 C11 122.15(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.3806(12) .
O1 C17 1.4373(15) .
O2 C13 1.3781(13) .
O2 C17 1.4285(14) .
N1 H1 0.8800 .
N1 C8 1.3940(13) .
N1 B1 1.4155(14) .
N2 H2 0.8800 .
N2 C10 1.3974(13) .
N2 B1 1.4188(15) .
C1 H1A 0.9500 .
C1 C2 1.4049(16) .
C1 C10 1.3769(15) .
C2 H2A 0.9500 .
C2 C3 1.3664(17) .
C3 H3 0.9500 .
C3 C4 1.4155(16) .
C4 C5 1.4141(16) .
C4 C9 1.4245(14) .
C5 H5 0.9500 .
C5 C6 1.3666(17) .
C6 H6 0.9500 .
C6 C7 1.4028(16) .
C7 H7 0.9500 .
C7 C8 1.3779(14) .
C8 C9 1.4221(14) .
C9 C10 1.4237(14) .
C11 C12 1.4117(14) .
C11 C16 1.3970(14) .
C11 B1 1.5671(15) .
C12 H12 0.9500 .
C12 C13 1.3706(15) .
C13 C14 1.3772(15) .
C14 C15 1.3689(15) .
C15 H15 0.9500 .
C15 C16 1.4016(14) .
C16 H16 0.9500 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C14 C15 C16 179.36(9) . . . .
O2 C13 C14 O1 -1.09(12) . . . .
O2 C13 C14 C15 178.04(9) . . . .
N1 C8 C9 C4 178.71(9) . . . .
N1 C8 C9 C10 0.87(14) . . . .
C1 C2 C3 C4 -0.68(17) . . . .
C2 C1 C10 N2 179.94(10) . . . .
C2 C1 C10 C9 1.47(15) . . . .
C2 C3 C4 C5 -177.31(10) . . . .
C2 C3 C4 C9 1.79(15) . . . .
C3 C4 C5 C6 -179.93(11) . . . .
C3 C4 C9 C8 -179.17(9) . . . .
C3 C4 C9 C10 -1.29(14) . . . .
C4 C5 C6 C7 -1.03(18) . . . .
C4 C9 C10 N2 -178.86(9) . . . .
C4 C9 C10 C1 -0.32(14) . . . .
C5 C4 C9 C8 -0.03(14) . . . .
C5 C4 C9 C10 177.85(9) . . . .
C5 C6 C7 C8 0.11(18) . . . .
C6 C7 C8 N1 -178.72(10) . . . .
C6 C7 C8 C9 0.84(16) . . . .
C7 C8 C9 C4 -0.87(15) . . . .
C7 C8 C9 C10 -178.71(9) . . . .
C8 N1 B1 N2 3.21(15) . . . .
C8 N1 B1 C11 -177.09(9) . . . .
C8 C9 C10 N2 -1.01(14) . . . .
C8 C9 C10 C1 177.52(9) . . . .
C9 C4 C5 C6 0.97(16) . . . .
C10 N2 B1 N1 -3.36(15) . . . .
C10 N2 B1 C11 176.94(9) . . . .
C10 C1 C2 C3 -0.99(17) . . . .
C11 C12 C13 O2 -178.01(10) . . . .
C11 C12 C13 C14 -0.22(17) . . . .
C12 C11 C16 C15 0.07(15) . . . .
C12 C11 B1 N1 -164.29(10) . . . .
C12 C11 B1 N2 15.39(15) . . . .
C12 C13 C14 O1 -179.24(10) . . . .
C12 C13 C14 C15 -0.11(17) . . . .
C13 O2 C17 O1 -20.81(12) . . . .
C13 C14 C15 C16 0.40(15) . . . .
C14 O1 C17 O2 20.11(11) . . . .
C14 C15 C16 C11 -0.39(15) . . . .
C16 C11 C12 C13 0.23(15) . . . .
C16 C11 B1 N1 15.55(15) . . . .
C16 C11 B1 N2 -164.77(9) . . . .
C17 O1 C14 C13 -11.87(11) . . . .
C17 O1 C14 C15 169.07(10) . . . .
C17 O2 C13 C12 -168.33(12) . . . .
C17 O2 C13 C14 13.66(12) . . . .
B1 N1 C8 C7 177.51(10) . . . .
B1 N1 C8 C9 -2.06(14) . . . .
B1 N2 C10 C1 -176.14(10) . . . .
B1 N2 C10 C9 2.36(14) . . . .
B1 C11 C12 C13 -179.92(9) . . . .
B1 C11 C16 C15 -179.77(9) . . . .
