data_bww18222
_audit_creation_date               2018-04-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_audit_update_record
;
????
;
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C20 H14 B N'
_chemical_formula_sum              'C20 H14 B N'
_chemical_formula_weight           279.13
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     8.2149(16)
_cell_length_b                     6.3407(13)
_cell_length_c                     13.524(3)
_cell_angle_alpha                  90
_cell_angle_beta                   95.51(3)
_cell_angle_gamma                  90
_cell_volume                       701.2(2)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      2141
_cell_measurement_temperature      153(2)
_cell_measurement_theta_max        27.4778
_cell_measurement_theta_min        2.4909
_shelx_estimated_absorpt_T_max     0.991
_shelx_estimated_absorpt_T_min     0.982
_exptl_absorpt_coefficient_mu      0.076
_exptl_absorpt_correction_T_max    1.0000
_exptl_absorpt_correction_T_min    0.9004
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.322
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               292
_exptl_crystal_size_max            0.24
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.12
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0399
_diffrn_reflns_av_unetI/netI       0.0394
_diffrn_reflns_Laue_measured_fraction_full  0.991
_diffrn_reflns_Laue_measured_fraction_max  0.991
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         8
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              8417
_diffrn_reflns_point_group_measured_fraction_full  0.990
_diffrn_reflns_point_group_measured_fraction_max  0.983
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.493
_diffrn_reflns_theta_min           2.788
_diffrn_ambient_temperature        153.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.991
_diffrn_measured_fraction_theta_max  0.991
_diffrn_measurement_device_type    'multiwire proportional'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.819
_reflns_Friedel_fraction_full      0.988
_reflns_Friedel_fraction_max       0.973
_reflns_number_gt                  2931
_reflns_number_total               3171
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.305
_refine_diff_density_min           -0.195
_refine_diff_density_rms           0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -4.3(10)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       199
_refine_ls_number_reflns           3171
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0663
_refine_ls_R_factor_gt             0.0616
_refine_ls_restrained_S_all        1.075
_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)+(0.0755P)²+0.2471P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1529
_refine_ls_wR_factor_ref           0.1577
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C13(H13), C11(H11), C7(H7), C8(H8), C12(H12), C15(H15), C2(H2),
 C17(H17), C20(H20), C5(H5), C16(H16), C3(H3), C4(H4)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 N1 N 0.3545(3) 0.5775(4) 0.61402(19) 0.0260(6) Uani 1 1 d . . . . .
 C18 C -0.0341(4) 0.2012(6) 0.2296(2) 0.0312(7) Uani 1 1 d . . . . .
 H18 H -0.0650 0.0717 0.2577 0.037 Uiso 1 1 calc R . . . .
 C6 C 0.3861(4) 0.3593(5) 0.7617(2) 0.0270(7) Uani 1 1 d . . . . .
 C19 C 0.0621(4) 0.3464(5) 0.2890(2) 0.0266(7) Uani 1 1 d . . . . .
 C13 C 0.2025(4) 0.6874(5) 0.3049(2) 0.0287(7) Uani 1 1 d . . . . .
 H13 H 0.2366 0.8147 0.2761 0.034 Uiso 1 1 calc R . . . .
 C11 C 0.3355(4) 0.7996(5) 0.4676(2) 0.0295(7) Uani 1 1 d . . . . .
 H11 H 0.3609 0.9316 0.4396 0.035 Uiso 1 1 calc R . . . .
 C7 C 0.2793(4) 0.2029(5) 0.7145(2) 0.0308(7) Uani 1 1 d . . . . .
 H7 H 0.2542 0.0812 0.7511 0.037 Uiso 1 1 calc R . . . .
 C8 C 0.2131(4) 0.2232(5) 0.6195(2) 0.0290(7) Uani 1 1 d . . . . .
 H8 H 0.1421 0.1181 0.5897 0.035 Uiso 1 1 calc R . . . .
 C12 C 0.3866(4) 0.7638(5) 0.5638(2) 0.0298(7) Uani 1 1 d . . . . .
 H12 H 0.4479 0.8710 0.5996 0.036 Uiso 1 1 calc R . . . .
 C15 C 0.0586(4) 0.5782(6) 0.1437(2) 0.0316(7) Uani 1 1 d . . . . .
 H15 H 0.0910 0.7046 0.1133 0.038 Uiso 1 1 calc R . . . .
 C2 C 0.5308(4) 0.6932(6) 0.7632(2) 0.0326(7) Uani 1 1 d . . . . .
 H2 H 0.5580 0.8197 0.7310 0.039 Uiso 1 1 calc R . . . .
 C17 C -0.0833(4) 0.2441(6) 0.1325(2) 0.0355(8) Uani 1 1 d . . . . .
 H17 H -0.1491 0.1455 0.0938 0.043 Uiso 1 1 calc R . . . .
 C20 C 0.1094(4) 0.3092(5) 0.3914(2) 0.0270(7) Uani 1 1 d . . . . .
 H20 H 0.0788 0.1803 0.4203 0.032 Uiso 1 1 calc R . . . .
 C1 C 0.4239(3) 0.5478(5) 0.7130(2) 0.0262(7) Uani 1 1 d . . . . .
 C14 C 0.1097(4) 0.5395(5) 0.2459(2) 0.0270(7) Uani 1 1 d . . . . .
 C10 C 0.2440(4) 0.6481(5) 0.4046(2) 0.0279(7) Uani 1 1 d . . . . .
 C5 C 0.4556(4) 0.3253(6) 0.8605(2) 0.0355(8) Uani 1 1 d . . . . .
 H5 H 0.4294 0.2002 0.8943 0.043 Uiso 1 1 calc R . . . .
 C16 C -0.0364(4) 0.4353(6) 0.0892(2) 0.0356(8) Uani 1 1 d . . . . .
 H16 H -0.0714 0.4645 0.0216 0.043 Uiso 1 1 calc R . . . .
 C9 C 0.1985(4) 0.4547(5) 0.4501(2) 0.0256(6) Uani 1 1 d . . . . .
 C3 C 0.5964(4) 0.6539(6) 0.8590(3) 0.0402(9) Uani 1 1 d . . . . .
 H3 H 0.6680 0.7546 0.8920 0.048 Uiso 1 1 calc R . . . .
 C4 C 0.5601(4) 0.4699(7) 0.9084(2) 0.0391(8) Uani 1 1 d . . . . .
 H4 H 0.6068 0.4445 0.9743 0.047 Uiso 1 1 calc R . . . .
 B1 B 0.2550(4) 0.4183(6) 0.5615(2) 0.0262(7) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 N1 C12 1.400(4) . ?
 N1 C1 1.416(4) . ?
 N1 B1 1.442(4) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.412(4) . ?
 C18 C17 1.364(4) . ?
 C6 C7 1.432(4) . ?
 C6 C1 1.414(4) . ?
 C6 C5 1.419(4) . ?
 C19 C20 1.422(4) . ?
 C19 C14 1.426(4) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.407(4) . ?
 C13 C10 1.381(4) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.348(4) . ?
 C11 C10 1.446(4) . ?
 C7 H7 0.9500 . ?
 C7 C8 1.353(4) . ?
 C8 H8 0.9500 . ?
 C8 B1 1.522(5) . ?
 C12 H12 0.9500 . ?
 C15 H15 0.9500 . ?
 C15 C14 1.428(4) . ?
 C15 C16 1.364(5) . ?
 C2 H2 0.9500 . ?
 C2 C1 1.403(4) . ?
 C2 C3 1.377(5) . ?
 C17 H17 0.9500 . ?
 C17 C16 1.416(5) . ?
 C20 H20 0.9500 . ?
 C20 C9 1.380(4) . ?
 C10 C9 1.437(4) . ?
 C5 H5 0.9500 . ?
 C5 C4 1.375(5) . ?
 C16 H16 0.9500 . ?
 C9 B1 1.551(4) . ?
 C3 H3 0.9500 . ?
 C3 C4 1.391(6) . ?
 C4 H4 0.9500 . ?

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
  _geom_angle_publ_flag
 C12 N1 C1 119.5(3) . . ?
 C12 N1 B1 118.4(3) . . ?
 C1 N1 B1 122.0(3) . . ?
 C19 C18 H18 119.5 . . ?
 C17 C18 H18 119.5 . . ?
 C17 C18 C19 121.0(3) . . ?
 C1 C6 C7 122.1(3) . . ?
 C1 C6 C5 118.7(3) . . ?
 C5 C6 C7 119.2(3) . . ?
 C18 C19 C20 122.1(3) . . ?
 C18 C19 C14 119.2(3) . . ?
 C20 C19 C14 118.7(3) . . ?
 C14 C13 H13 119.9 . . ?
 C10 C13 H13 119.9 . . ?
 C10 C13 C14 120.2(3) . . ?
 C12 C11 H11 118.2 . . ?
 C12 C11 C10 123.6(3) . . ?
 C10 C11 H11 118.2 . . ?
 C6 C7 H7 119.0 . . ?
 C8 C7 C6 122.0(3) . . ?
 C8 C7 H7 119.0 . . ?
 C7 C8 H8 120.8 . . ?
 C7 C8 B1 118.5(3) . . ?
 B1 C8 H8 120.8 . . ?
 N1 C12 H12 118.2 . . ?
 C11 C12 N1 123.7(3) . . ?
 C11 C12 H12 118.2 . . ?
 C14 C15 H15 119.7 . . ?
 C16 C15 H15 119.7 . . ?
 C16 C15 C14 120.5(3) . . ?
 C1 C2 H2 119.8 . . ?
 C3 C2 H2 119.8 . . ?
 C3 C2 C1 120.5(3) . . ?
 C18 C17 H17 120.0 . . ?
 C18 C17 C16 120.1(3) . . ?
 C16 C17 H17 120.0 . . ?
 C19 C20 H20 119.0 . . ?
 C9 C20 C19 122.0(3) . . ?
 C9 C20 H20 119.0 . . ?
 C6 C1 N1 117.8(3) . . ?
 C2 C1 N1 123.1(3) . . ?
 C2 C1 C6 119.0(3) . . ?
 C19 C14 C15 118.4(3) . . ?
 C13 C14 C19 119.7(3) . . ?
 C13 C14 C15 121.8(3) . . ?
 C13 C10 C11 121.4(3) . . ?
 C13 C10 C9 121.4(3) . . ?
 C9 C10 C11 117.2(3) . . ?
 C6 C5 H5 119.4 . . ?
 C4 C5 C6 121.3(3) . . ?
 C4 C5 H5 119.4 . . ?
 C15 C16 C17 120.7(3) . . ?
 C15 C16 H16 119.7 . . ?
 C17 C16 H16 119.7 . . ?
 C20 C9 C10 118.0(3) . . ?
 C20 C9 B1 123.5(3) . . ?
 C10 C9 B1 118.5(3) . . ?
 C2 C3 H3 119.3 . . ?
 C2 C3 C4 121.4(3) . . ?
 C4 C3 H3 119.3 . . ?
 C5 C4 C3 119.1(3) . . ?
 C5 C4 H4 120.5 . . ?
 C3 C4 H4 120.5 . . ?
 N1 B1 C8 117.4(3) . . ?
 N1 B1 C9 118.5(3) . . ?
 C8 B1 C9 124.1(3) . . ?

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
  _geom_torsion_publ_flag
 C18 C19 C20 C9 -177.7(3) . . . . ?
 C18 C19 C14 C13 178.6(3) . . . . ?
 C18 C19 C14 C15 -0.3(4) . . . . ?
 C18 C17 C16 C15 0.2(5) . . . . ?
 C6 C7 C8 B1 0.3(5) . . . . ?
 C6 C5 C4 C3 0.7(5) . . . . ?
 C19 C18 C17 C16 0.8(5) . . . . ?
 C19 C20 C9 C10 -0.2(4) . . . . ?
 C19 C20 C9 B1 -178.9(3) . . . . ?
 C13 C10 C9 C20 -0.9(4) . . . . ?
 C13 C10 C9 B1 177.8(3) . . . . ?
 C11 C10 C9 C20 179.2(3) . . . . ?
 C11 C10 C9 B1 -2.1(4) . . . . ?
 C7 C6 C1 N1 -1.0(4) . . . . ?
 C7 C6 C1 C2 -179.4(3) . . . . ?
 C7 C6 C5 C4 179.3(3) . . . . ?
 C7 C8 B1 N1 -4.2(4) . . . . ?
 C7 C8 B1 C9 175.4(3) . . . . ?
 C12 N1 C1 C6 178.9(3) . . . . ?
 C12 N1 C1 C2 -2.9(4) . . . . ?
 C12 N1 B1 C8 -176.3(3) . . . . ?
 C12 N1 B1 C9 4.1(4) . . . . ?
 C12 C11 C10 C13 -176.2(3) . . . . ?
 C12 C11 C10 C9 3.6(4) . . . . ?
 C2 C3 C4 C5 -0.4(6) . . . . ?
 C17 C18 C19 C20 177.4(3) . . . . ?
 C17 C18 C19 C14 -0.7(4) . . . . ?
 C20 C19 C14 C13 0.4(4) . . . . ?
 C20 C19 C14 C15 -178.5(3) . . . . ?
 C20 C9 B1 N1 177.0(3) . . . . ?
 C20 C9 B1 C8 -2.6(4) . . . . ?
 C1 N1 C12 C11 175.2(3) . . . . ?
 C1 N1 B1 C8 5.7(4) . . . . ?
 C1 N1 B1 C9 -173.9(2) . . . . ?
 C1 C6 C7 C8 2.4(5) . . . . ?
 C1 C6 C5 C4 -1.1(5) . . . . ?
 C1 C2 C3 C4 0.4(5) . . . . ?
 C14 C19 C20 C9 0.5(4) . . . . ?
 C14 C13 C10 C11 -178.3(3) . . . . ?
 C14 C13 C10 C9 1.8(4) . . . . ?
 C14 C15 C16 C17 -1.3(5) . . . . ?
 C10 C13 C14 C19 -1.5(4) . . . . ?
 C10 C13 C14 C15 177.4(3) . . . . ?
 C10 C11 C12 N1 -1.2(5) . . . . ?
 C10 C9 B1 N1 -1.7(4) . . . . ?
 C10 C9 B1 C8 178.8(3) . . . . ?
 C5 C6 C7 C8 -178.0(3) . . . . ?
 C5 C6 C1 N1 179.4(3) . . . . ?
 C5 C6 C1 C2 1.0(4) . . . . ?
 C16 C15 C14 C19 1.3(5) . . . . ?
 C16 C15 C14 C13 -177.6(3) . . . . ?
 C3 C2 C1 N1 -179.0(3) . . . . ?
 C3 C2 C1 C6 -0.7(5) . . . . ?
 B1 N1 C12 C11 -2.9(4) . . . . ?
 B1 N1 C1 C6 -3.1(4) . . . . ?
 B1 N1 C1 C2 175.2(3) . . . . ?


_olex2_submission_special_instructions  'No special instructions were received'
