#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:35:42 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/88/4038818.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_4038818
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         'C18 H21 N2 +, B F4 -'
_chemical_formula_sum            'C18 H21 B F4 N2'
_chemical_formula_weight         352.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 100.6970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1916(6)
_cell_length_b                   9.9536(5)
_cell_length_c                   14.3268(7)
_cell_measurement_reflns_used    4883
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.51
_cell_volume                     1708.35(15)
_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 0.997
_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  0.0494
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25607
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.046
_diffrn_reflns_theta_min         2.506
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_description       plate
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0386
_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)+(0.0427P)²+0.5604P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.1026
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3031
_reflns_number_total             4122
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01697_si_001.cif
_cod_data_source_block           Struct-5
_cod_depositor_comments
'Adding full bibliography for 4038815--4038822.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038818
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.63888(9) 0.72270(12) 0.02732(8) 0.0203(2) Uani 1 1 d . . . . .
N2 N 0.83885(9) 0.59335(11) 0.00156(8) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.83448(11) 0.82508(14) 0.06808(9) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.71610(11) 0.83466(13) 0.06382(9) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.66786(12) 0.94619(14) 0.09521(10) 0.0228(3) Uani 1 1 d . . . . .
H3A H 0.5894 0.9483 0.0923 0.027 Uiso 1 1 calc R U . . .
C4 C 0.73292(13) 1.05734(15) 0.13163(10) 0.0261(3) Uani 1 1 d . . . . .
H4A H 0.6987 1.1341 0.1533 0.031 Uiso 1 1 calc R U . . .
C5 C 0.84570(13) 1.05448(15) 0.13576(10) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.8893 1.1304 0.1595 0.031 Uiso 1 1 calc R U . . .
C6 C 0.89894(12) 0.94009(14) 0.10518(9) 0.0220(3) Uani 1 1 d . . . . .
C7 C 1.01689(12) 0.93928(15) 0.11236(10) 0.0259(3) Uani 1 1 d . . . . .
H7A H 1.0586 1.0171 0.1352 0.031 Uiso 1 1 calc R U . . .
C8 C 1.07144(12) 0.82933(16) 0.08721(11) 0.0286(3) Uani 1 1 d . . . . .
H8A H 1.1504 0.8296 0.0939 0.034 Uiso 1 1 calc R U . . .
C9 C 1.00941(12) 0.71552(15) 0.05120(10) 0.0259(3) Uani 1 1 d . . . . .
H9A H 1.0474 0.6388 0.0339 0.031 Uiso 1 1 calc R U . . .
C10 C 0.89551(11) 0.71271(14) 0.04054(9) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.54951(12) 0.76437(16) -0.05510(10) 0.0277(3) Uani 1 1 d . . . . .
H11A H 0.5837 0.8132 -0.1018 0.042 Uiso 1 1 calc R U . . .
H11B H 0.4954 0.8227 -0.0321 0.042 Uiso 1 1 calc R U . . .
H11C H 0.5113 0.6843 -0.0849 0.042 Uiso 1 1 calc R U . . .
C12 C 0.58899(12) 0.65781(15) 0.10490(11) 0.0267(3) Uani 1 1 d . . . . .
H12A H 0.6490 0.6285 0.1562 0.040 Uiso 1 1 calc R U . . .
H12B H 0.5442 0.5800 0.0791 0.040 Uiso 1 1 calc R U . . .
H12C H 0.5414 0.7228 0.1298 0.040 Uiso 1 1 calc R U . . .
C13 C 0.80995(11) 0.48609(14) 0.05499(10) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.73890(12) 0.40560(15) -0.00597(11) 0.0259(3) Uani 1 1 d . . . . .
H14A H 0.7053 0.3251 0.0106 0.031 Uiso 1 1 calc R U . . .
C15 C 0.72396(12) 0.46335(15) -0.09863(11) 0.0265(3) Uani 1 1 d . . . . .
H15A H 0.6787 0.4280 -0.1544 0.032 Uiso 1 1 calc R U . . .
C16 C 0.78612(11) 0.57857(14) -0.09327(9) 0.0229(3) Uani 1 1 d . . . . .
C17 C 0.85914(13) 0.47276(16) 0.15787(10) 0.0288(3) Uani 1 1 d . . . . .
H17A H 0.8217 0.3997 0.1855 0.043 Uiso 1 1 calc R U . . .
H17B H 0.8490 0.5571 0.1906 0.043 Uiso 1 1 calc R U . . .
H17C H 0.9390 0.4527 0.1652 0.043 Uiso 1 1 calc R U . . .
C18 C 0.80395(14) 0.67868(16) -0.16690(10) 0.0301(3) Uani 1 1 d . . . . .
H18A H 0.7542 0.6579 -0.2271 0.045 Uiso 1 1 calc R U . . .
H18B H 0.8817 0.6746 -0.1757 0.045 Uiso 1 1 calc R U . . .
H18C H 0.7876 0.7691 -0.1461 0.045 Uiso 1 1 calc R U . . .
B1 B 0.61609(14) 0.42323(17) 0.30541(12) 0.0241(3) Uani 1 1 d . . . . .
F1 F 0.69977(8) 0.52006(9) 0.31663(7) 0.0372(2) Uani 1 1 d . . . . .
F2 F 0.60758(8) 0.37302(10) 0.39473(6) 0.0381(2) Uani 1 1 d . . . . .
F3 F 0.51520(8) 0.48164(12) 0.26482(8) 0.0513(3) Uani 1 1 d . . . . .
F4 F 0.64202(10) 0.32133(11) 0.24814(8) 0.0505(3) Uani 1 1 d . . . . .
H1 H 0.6787(14) 0.6594(17) 0.0037(12) 0.027(4) Uiso 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
C2 N1 C12 112.14(11) . . ?
C2 N1 C11 112.75(11) . . ?
C12 N1 C11 111.29(11) . . ?
C2 N1 H1 107.8(10) . . ?
C12 N1 H1 107.3(11) . . ?
C11 N1 H1 105.1(10) . . ?
C13 N2 C16 109.56(11) . . ?
C13 N2 C10 124.90(11) . . ?
C16 N2 C10 124.51(11) . . ?
C6 C1 C2 116.11(12) . . ?
C6 C1 C10 116.54(12) . . ?
C2 C1 C10 127.35(12) . . ?
C3 C2 C1 121.92(13) . . ?
C3 C2 N1 116.07(12) . . ?
C1 C2 N1 121.99(12) . . ?
C2 C3 C4 120.85(13) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 119.64(13) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 121.18(13) . . ?
C4 C5 H5A 119.4 . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C7 119.75(13) . . ?
C5 C6 C1 120.28(13) . . ?
C7 C6 C1 119.96(13) . . ?
C8 C7 C6 121.44(13) . . ?
C8 C7 H7A 119.3 . . ?
C6 C7 H7A 119.3 . . ?
C7 C8 C9 119.22(13) . . ?
C7 C8 H8A 120.4 . . ?
C9 C8 H8A 120.4 . . ?
C10 C9 C8 121.53(14) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 N2 117.75(12) . . ?
C9 C10 C1 121.27(13) . . ?
N2 C10 C1 120.97(12) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N2 106.97(12) . . ?
C14 C13 C17 132.04(14) . . ?
N2 C13 C17 120.93(13) . . ?
C13 C14 C15 108.31(13) . . ?
C13 C14 H14A 125.8 . . ?
C15 C14 H14A 125.8 . . ?
C16 C15 C14 108.16(13) . . ?
C16 C15 H15A 125.9 . . ?
C14 C15 H15A 125.9 . . ?
C15 C16 N2 107.00(12) . . ?
C15 C16 C18 132.06(13) . . ?
N2 C16 C18 120.94(13) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F4 B1 F3 110.03(13) . . ?
F4 B1 F1 109.54(13) . . ?
F3 B1 F1 109.41(13) . . ?
F4 B1 F2 110.29(13) . . ?
F3 B1 F2 108.87(12) . . ?
F1 B1 F2 108.66(12) . . ?
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 C2 1.4896(17) . ?
N1 C12 1.5078(18) . ?
N1 C11 1.5086(18) . ?
N1 H1 0.899(17) . ?
N2 C13 1.3964(18) . ?
N2 C16 1.3988(17) . ?
N2 C10 1.4343(17) . ?
C1 C6 1.4337(19) . ?
C1 C2 1.4364(18) . ?
C1 C10 1.4385(19) . ?
C2 C3 1.3707(19) . ?
C3 C4 1.404(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.365(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.420(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.422(2) . ?
C7 C8 1.363(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.406(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3688(19) . ?
C9 H9A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.369(2) . ?
C13 C17 1.491(2) . ?
C14 C15 1.427(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.369(2) . ?
C15 H15A 0.9500 . ?
C16 C18 1.496(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
B1 F4 1.3777(19) . ?
B1 F3 1.3870(19) . ?
B1 F1 1.3909(19) . ?
B1 F2 1.3956(18) . ?
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
C6 C1 C2 C3 -1.29(18) . . . . ?
C10 C1 C2 C3 177.82(13) . . . . ?
C6 C1 C2 N1 -179.72(11) . . . . ?
C10 C1 C2 N1 -0.6(2) . . . . ?
C12 N1 C2 C3 -67.61(15) . . . . ?
C11 N1 C2 C3 58.95(16) . . . . ?
C12 N1 C2 C1 110.90(14) . . . . ?
C11 N1 C2 C1 -122.54(13) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
N1 C2 C3 C4 179.60(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 -178.63(13) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C2 C1 C6 C5 0.40(18) . . . . ?
C10 C1 C6 C5 -178.81(12) . . . . ?
C2 C1 C6 C7 179.75(12) . . . . ?
C10 C1 C6 C7 0.54(18) . . . . ?
C5 C6 C7 C8 177.40(14) . . . . ?
C1 C6 C7 C8 -2.0(2) . . . . ?
C6 C7 C8 C9 1.6(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 N2 178.83(13) . . . . ?
C8 C9 C10 C1 -1.6(2) . . . . ?
C13 N2 C10 C9 93.32(16) . . . . ?
C16 N2 C10 C9 -99.51(16) . . . . ?
C13 N2 C10 C1 -86.23(16) . . . . ?
C16 N2 C10 C1 80.94(17) . . . . ?
C6 C1 C10 C9 1.20(19) . . . . ?
C2 C1 C10 C9 -177.91(13) . . . . ?
C6 C1 C10 N2 -179.27(11) . . . . ?
C2 C1 C10 N2 1.6(2) . . . . ?
C16 N2 C13 C14 -0.52(15) . . . . ?
C10 N2 C13 C14 168.29(12) . . . . ?
C16 N2 C13 C17 176.86(12) . . . . ?
C10 N2 C13 C17 -14.33(19) . . . . ?
N2 C13 C14 C15 0.30(15) . . . . ?
C17 C13 C14 C15 -176.67(14) . . . . ?
C13 C14 C15 C16 0.02(16) . . . . ?
C14 C15 C16 N2 -0.33(16) . . . . ?
C14 C15 C16 C18 179.13(15) . . . . ?
C13 N2 C16 C15 0.53(15) . . . . ?
C10 N2 C16 C15 -168.33(12) . . . . ?
C13 N2 C16 C18 -179.00(12) . . . . ?
C10 N2 C16 C18 12.1(2) . . . . ?
