#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:42 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038819.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_4038819
loop_
_publ_author_name
'Pozharskii, Alexander F.'
'Dyablo, Olga V.'
'Pogosova, Olga G.'
'Ozeryanskii, Valery A.'
'Filarowski, Aleksander'
'Vasilikhina, Kseniya M.'
'Dzhangiryan, Narek A.'
_publ_section_title
;
 Modeling Biologically Important NH···π Interactions
 Using peri-Disubstituted Naphthalenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12468
_journal_page_last               12481
_journal_paper_doi               10.1021/acs.joc.0c01697
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C19 H14 N +, B F4 -'
_chemical_formula_sum            'C19 H14 B F4 N'
_chemical_formula_weight         343.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 99.854(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3874(6)
_cell_length_b                   12.2927(9)
_cell_length_c                   15.2185(11)
_cell_measurement_reflns_used    6669
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.60
_cell_volume                     1545.94(19)
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_collection       'APEX (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_publication_material
'SHELXL-2014/6 (Sheldrick, 2014) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.019
_diffrn_reflns_theta_min         2.142
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       prizm
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0430
_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)+(0.0588P)²+0.5973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1193
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3055
_reflns_number_total             3741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-6
_cod_depositor_comments
'Adding full bibliography for 4038815--4038822.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4038819
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_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 0.52870(13) 0.86940(9) 0.15932(7) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.520(2) 0.9199(16) 0.2011(13) 0.034(5) Uiso 1 1 d . . . . .
C1 C 0.45591(16) 0.77315(11) 0.16565(9) 0.0210(3) Uani 1 1 d . . . . .
H1A H 0.3978 0.7606 0.2131 0.025 Uiso 1 1 calc R U . . .
C2 C 0.46493(17) 0.69207(11) 0.10364(9) 0.0223(3) Uani 1 1 d . . . . .
H2A H 0.4172 0.6228 0.1090 0.027 Uiso 1 1 calc R U . . .
C3 C 0.54491(16) 0.71438(11) 0.03384(9) 0.0216(3) Uani 1 1 d . . . . .
H3A H 0.5497 0.6604 -0.0103 0.026 Uiso 1 1 calc R U . . .
C4 C 0.61960(15) 0.81572(11) 0.02682(8) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.69690(16) 0.83896(12) -0.04808(9) 0.0221(3) Uani 1 1 d . . . . .
H5A H 0.7013 0.7849 -0.0922 0.027 Uiso 1 1 calc R U . . .
C6 C 0.76341(16) 0.93769(12) -0.05575(9) 0.0223(3) Uani 1 1 d . . . . .
H6A H 0.8097 0.9537 -0.1070 0.027 Uiso 1 1 calc R U . . .
C7 C 0.76558(15) 1.01904(11) 0.01207(9) 0.0196(3) Uani 1 1 d . . . . .
C8 C 0.83931(17) 1.11992(11) -0.00002(10) 0.0232(3) Uani 1 1 d . . . . .
H8A H 0.8847 1.1323 -0.0522 0.028 Uiso 1 1 calc R U . . .
C9 C 0.84581(18) 1.20010(12) 0.06310(10) 0.0252(3) Uani 1 1 d . . . . .
H9A H 0.8932 1.2685 0.0541 0.030 Uiso 1 1 calc R U . . .
C10 C 0.78221(17) 1.18067(11) 0.14094(9) 0.0235(3) Uani 1 1 d . . . . .
H10A H 0.7866 1.2371 0.1839 0.028 Uiso 1 1 calc R U . . .
C11 C 0.71281(16) 1.08164(11) 0.15758(9) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.69751(15) 0.99945(10) 0.09048(9) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.61601(15) 0.89515(10) 0.09369(9) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.67295(16) 1.06910(11) 0.24927(9) 0.0203(3) Uani 1 1 d . . . . .
C15 C 0.56984(18) 1.14350(12) 0.28090(9) 0.0245(3) Uani 1 1 d . . . . .
H15A H 0.5147 1.1966 0.2417 0.029 Uiso 1 1 calc R U . . .
C16 C 0.54758(18) 1.14016(13) 0.36940(10) 0.0279(3) Uani 1 1 d . . . . .
H16A H 0.4764 1.1905 0.3900 0.033 Uiso 1 1 calc R U . . .
C17 C 0.62878(19) 1.06367(13) 0.42782(10) 0.0279(3) Uani 1 1 d . . . . .
H17A H 0.6143 1.0621 0.4884 0.033 Uiso 1 1 calc R U . . .
C18 C 0.73131(18) 0.98955(12) 0.39693(10) 0.0259(3) Uani 1 1 d . . . . .
H18A H 0.7867 0.9371 0.4367 0.031 Uiso 1 1 calc R U . . .
C19 C 0.75388(16) 0.99123(11) 0.30833(9) 0.0222(3) Uani 1 1 d . . . . .
H19A H 0.8238 0.9399 0.2879 0.027 Uiso 1 1 calc R U . . .
F1 F 0.17794(13) 1.05042(7) 0.26226(6) 0.0362(2) Uani 1 1 d . . . . .
F2 F 0.13823(11) 0.92668(8) 0.36753(6) 0.0337(2) Uani 1 1 d . . . . .
F3 F 0.36139(11) 0.91434(8) 0.30129(7) 0.0369(2) Uani 1 1 d . . . . .
F4 F 0.11342(12) 0.87559(8) 0.22136(7) 0.0398(3) Uani 1 1 d . . . . .
B1 B 0.1964(2) 0.94211(14) 0.28791(11) 0.0246(3) 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 0.0033 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C1 N1 C13 124.15(12) . . ?
C1 N1 H1 117.7(12) . . ?
C13 N1 H1 118.1(12) . . ?
N1 C1 C2 120.48(12) . . ?
N1 C1 H1A 119.8 . . ?
C2 C1 H1A 119.8 . . ?
C3 C2 C1 118.25(13) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 121.12(12) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 C13 119.49(12) . . ?
C3 C4 C5 120.33(12) . . ?
C13 C4 C5 120.18(12) . . ?
C6 C5 C4 119.88(13) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C5 C6 C7 121.28(13) . . ?
C5 C6 H6A 119.4 . . ?
C7 C6 H6A 119.4 . . ?
C8 C7 C12 120.24(12) . . ?
C8 C7 C6 118.05(13) . . ?
C12 C7 C6 121.71(12) . . ?
C9 C8 C7 120.39(13) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 119.67(13) . . ?
C8 C9 H9A 120.2 . . ?
C10 C9 H9A 120.2 . . ?
C11 C10 C9 122.34(13) . . ?
C11 C10 H10A 118.8 . . ?
C9 C10 H10A 118.8 . . ?
C10 C11 C12 118.60(12) . . ?
C10 C11 C14 115.26(12) . . ?
C12 C11 C14 125.95(12) . . ?
C11 C12 C7 118.59(12) . . ?
C11 C12 C13 125.75(12) . . ?
C7 C12 C13 115.65(12) . . ?
N1 C13 C4 116.36(12) . . ?
N1 C13 C12 122.60(12) . . ?
C4 C13 C12 121.02(12) . . ?
C15 C14 C19 118.96(13) . . ?
C15 C14 C11 120.19(12) . . ?
C19 C14 C11 120.37(12) . . ?
C16 C15 C14 120.45(13) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C17 C16 C15 120.46(14) . . ?
C17 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
C18 C17 C16 119.42(14) . . ?
C18 C17 H17A 120.3 . . ?
C16 C17 H17A 120.3 . . ?
C17 C18 C19 120.82(13) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C18 C19 C14 119.88(13) . . ?
C18 C19 H19A 120.1 . . ?
C14 C19 H19A 120.1 . . ?
F1 B1 F4 109.92(13) . . ?
F1 B1 F2 109.61(12) . . ?
F4 B1 F2 110.25(13) . . ?
F1 B1 F3 109.48(13) . . ?
F4 B1 F3 108.67(12) . . ?
F2 B1 F3 108.87(13) . . ?
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 C1 1.3424(17) . ?
N1 C13 1.3728(17) . ?
N1 H1 0.90(2) . ?
C1 C2 1.3836(19) . ?
C1 H1A 0.9500 . ?
C2 C3 1.377(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4066(19) . ?
C3 H3A 0.9500 . ?
C4 C13 1.4144(18) . ?
C4 C5 1.4333(19) . ?
C5 C6 1.349(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4350(19) . ?
C6 H6A 0.9500 . ?
C7 C8 1.4117(19) . ?
C7 C12 1.4287(18) . ?
C8 C9 1.371(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.400(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3912(19) . ?
C10 H10A 0.9500 . ?
C11 C12 1.4266(18) . ?
C11 C14 1.4974(19) . ?
C12 C13 1.4577(18) . ?
C14 C15 1.3995(19) . ?
C14 C19 1.4057(19) . ?
C15 C16 1.392(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.393(2) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
F1 B1 1.3887(19) . ?
F2 B1 1.3947(18) . ?
F3 B1 1.4055(19) . ?
F4 B1 1.3921(19) . ?
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
C13 N1 C1 C2 -0.3(2) . . . . ?
N1 C1 C2 C3 -2.4(2) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C2 C3 C4 C13 1.56(19) . . . . ?
C2 C3 C4 C5 -177.60(13) . . . . ?
C3 C4 C5 C6 177.75(13) . . . . ?
C13 C4 C5 C6 -1.40(19) . . . . ?
C4 C5 C6 C7 3.1(2) . . . . ?
C5 C6 C7 C8 179.13(13) . . . . ?
C5 C6 C7 C12 -0.1(2) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C6 C7 C8 C9 -179.47(13) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C8 C9 C10 C11 0.6(2) . . . . ?
C9 C10 C11 C12 -3.8(2) . . . . ?
C9 C10 C11 C14 171.46(13) . . . . ?
C10 C11 C12 C7 4.90(18) . . . . ?
C14 C11 C12 C7 -169.80(12) . . . . ?
C10 C11 C12 C13 -174.52(12) . . . . ?
C14 C11 C12 C13 10.8(2) . . . . ?
C8 C7 C12 C11 -2.99(18) . . . . ?
C6 C7 C12 C11 176.21(12) . . . . ?
C8 C7 C12 C13 176.48(12) . . . . ?
C6 C7 C12 C13 -4.31(18) . . . . ?
C1 N1 C13 C4 3.62(18) . . . . ?
C1 N1 C13 C12 -178.11(12) . . . . ?
C3 C4 C13 N1 -4.12(18) . . . . ?
C5 C4 C13 N1 175.04(11) . . . . ?
C3 C4 C13 C12 177.58(12) . . . . ?
C5 C4 C13 C12 -3.26(19) . . . . ?
C11 C12 C13 N1 7.1(2) . . . . ?
C7 C12 C13 N1 -172.29(11) . . . . ?
C11 C12 C13 C4 -174.66(12) . . . . ?
C7 C12 C13 C4 5.91(17) . . . . ?
C10 C11 C14 C15 57.37(17) . . . . ?
C12 C11 C14 C15 -127.77(15) . . . . ?
C10 C11 C14 C19 -114.63(14) . . . . ?
C12 C11 C14 C19 60.22(19) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C11 C14 C15 C16 -172.28(13) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C17 C18 C19 0.2(2) . . . . ?
C17 C18 C19 C14 0.4(2) . . . . ?
C15 C14 C19 C18 -0.4(2) . . . . ?
C11 C14 C19 C18 171.74(12) . . . . ?
