#------------------------------------------------------------------------------
#$Date: 2016-07-04 15:36:21 +0300 (Mon, 04 Jul 2016) $
#$Revision: 184156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/20/4032004.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_4032004
loop_
_publ_author_name
'Pozharskii, Alexander F.'
'Ozeryanskii, Valery A.'
'Mikshiev, Vladimir Y.'
'Antonov, Alexander S.'
'Chernyshev, Anatoly V.'
'Metelitsa, Anatoly V.'
'Borodkin, Gennady S.'
'Fedik, Nikita S.'
'Dyablo, Olga V.'
_publ_section_title
;
 10-Dimethylamino Derivatives of Benzo[h]quinoline and
 Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed
 peri-NMe2/-N═ Groups. How to Distinguish between Proton Sponges
 and Pseudo-Proton Sponges.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5574
_journal_page_last               5587
_journal_paper_doi               10.1021/acs.joc.6b00917
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C15 H15 N2 +, B F4 -'
_chemical_formula_sum            'C15 H15 B F4 N2'
_chemical_formula_weight         310.10
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.073(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2123(9)
_cell_length_b                   11.7333(17)
_cell_length_c                   9.8071(14)
_cell_measurement_reflns_used    2555
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.06
_cell_measurement_theta_min      2.75
_cell_volume                     696.32(17)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8720
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow-brown
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         1941
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0270P)²+0.6049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1657
_reflns_number_total             1941
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo6b00917_si_002.cif
_cod_data_source_block           s25
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21  '
_cod_database_code               4032004
_chemical_absolute_structure     syn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.0742(4) 0.8781(2) 0.5723(3) 0.0218(5) Uani 1 1 d .
N2 N 0.4032(4) 0.9577(2) 0.7647(2) 0.0200(5) Uani 1 1 d .
H2 H 0.279(6) 0.911(3) 0.722(3) 0.028(9) Uiso 1 1 d .
C1 C -0.1153(5) 0.8205(3) 0.5396(4) 0.0275(6) Uani 1 1 d .
H1A H -0.1659 0.7825 0.6120 0.033 Uiso 1 1 calc R
C2 C -0.2422(5) 0.8139(3) 0.4027(4) 0.0301(7) Uani 1 1 d .
H2A H -0.3786 0.7739 0.3829 0.036 Uiso 1 1 calc R
C3 C -0.1672(5) 0.8660(3) 0.2978(3) 0.0298(7) Uani 1 1 d .
H3A H -0.2506 0.8611 0.2040 0.036 Uiso 1 1 calc R
C4 C 0.0327(5) 0.9268(3) 0.3282(3) 0.0249(6) Uani 1 1 d .
C5 C 0.1202(5) 0.9832(3) 0.2229(3) 0.0291(7) Uani 1 1 d .
H5A H 0.0438 0.9784 0.1275 0.035 Uiso 1 1 calc R
C6 C 0.3091(5) 1.0428(3) 0.2579(3) 0.0284(6) Uani 1 1 d .
H6A H 0.3639 1.0793 0.1862 0.034 Uiso 1 1 calc R
C7 C 0.4304(5) 1.0531(3) 0.3997(3) 0.0220(6) Uani 1 1 d .
C8 C 0.6277(5) 1.1166(3) 0.4333(3) 0.0243(6) Uani 1 1 d .
H8A H 0.6809 1.1525 0.3606 0.029 Uiso 1 1 calc R
C9 C 0.7437(5) 1.1274(3) 0.5684(3) 0.0254(6) Uani 1 1 d .
H9A H 0.8762 1.1708 0.5887 0.030 Uiso 1 1 calc R
C10 C 0.6686(5) 1.0749(3) 0.6775(3) 0.0230(6) Uani 1 1 d .
H10A H 0.7486 1.0837 0.7716 0.028 Uiso 1 1 calc R
C11 C 0.4788(4) 1.0108(2) 0.6475(3) 0.0189(6) Uani 1 1 d .
C12 C 0.3515(5) 0.9976(2) 0.5083(3) 0.0186(5) Uani 1 1 d .
C13 C 0.1478(5) 0.9325(2) 0.4699(3) 0.0193(5) Uani 1 1 d .
C14 C 0.3112(5) 1.0451(3) 0.8485(3) 0.0296(7) Uani 1 1 d .
H14A H 0.1929 1.0878 0.7863 0.044 Uiso 1 1 calc R
H14B H 0.4289 1.0977 0.8928 0.044 Uiso 1 1 calc R
H14C H 0.2519 1.0067 0.9208 0.044 Uiso 1 1 calc R
C15 C 0.5780(5) 0.8861(3) 0.8545(4) 0.0359(8) Uani 1 1 d .
H15A H 0.6298 0.8289 0.7964 0.054 Uiso 1 1 calc R
H15B H 0.5169 0.8477 0.9261 0.054 Uiso 1 1 calc R
H15C H 0.7020 0.9346 0.8998 0.054 Uiso 1 1 calc R
F1 F 0.3197(3) 0.77752(18) 0.08490(19) 0.0364(5) Uani 1 1 d .
F2 F 0.0806(3) 0.8112(2) -0.1230(3) 0.0562(7) Uani 1 1 d .
F3 F -0.0112(4) 0.6857(3) 0.0274(2) 0.0638(8) Uani 1 1 d .
F4 F 0.2590(4) 0.6454(3) -0.0859(3) 0.0724(9) Uani 1 1 d .
B1 B 0.1584(6) 0.7300(3) -0.0226(4) 0.0282(7) 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 0.0000 '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'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0000 '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
C1 N1 C13 119.3(3)
C11 N2 C15 112.3(2)
C11 N2 C14 111.4(2)
C15 N2 C14 112.2(2)
C11 N2 H2 105(2)
C15 N2 H2 110(2)
C14 N2 H2 105(2)
N1 C1 C2 122.4(3)
N1 C1 H1A 118.8
C2 C1 H1A 118.8
C3 C2 C1 119.0(3)
C3 C2 H2A 120.5
C1 C2 H2A 120.5
C2 C3 C4 120.2(3)
C2 C3 H3A 119.9
C4 C3 H3A 119.9
C3 C4 C13 117.3(3)
C3 C4 C5 122.9(3)
C13 C4 C5 119.8(3)
C6 C5 C4 120.6(3)
C6 C5 H5A 119.7
C4 C5 H5A 119.7
C5 C6 C7 122.1(3)
C5 C6 H6A 119.0
C7 C6 H6A 119.0
C8 C7 C12 119.6(3)
C8 C7 C6 120.8(3)
C12 C7 C6 119.6(3)
C9 C8 C7 121.2(3)
C9 C8 H8A 119.4
C7 C8 H8A 119.4
C8 C9 C10 120.4(3)
C8 C9 H9A 119.8
C10 C9 H9A 119.8
C11 C10 C9 119.6(3)
C11 C10 H10A 120.2
C9 C10 H10A 120.2
C10 C11 C12 121.9(3)
C10 C11 N2 118.3(2)
C12 C11 N2 119.8(2)
C11 C12 C7 117.2(2)
C11 C12 C13 124.6(2)
C7 C12 C13 118.2(2)
N1 C13 C4 121.8(3)
N1 C13 C12 118.4(2)
C4 C13 C12 119.8(2)
N2 C14 H14A 109.5
N2 C14 H14B 109.5
H14A C14 H14B 109.5
N2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 C15 H15A 109.5
N2 C15 H15B 109.5
H15A C15 H15B 109.5
N2 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
F3 B1 F2 110.3(3)
F3 B1 F4 110.5(3)
F2 B1 F4 107.2(3)
F3 B1 F1 111.3(3)
F2 B1 F1 109.9(3)
F4 B1 F1 107.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.332(4)
N1 C13 1.353(4)
N2 C11 1.474(3)
N2 C15 1.493(4)
N2 C14 1.505(4)
N2 H2 0.96(4)
C1 C2 1.397(4)
C1 H1A 0.9500
C2 C3 1.365(5)
C2 H2A 0.9500
C3 C4 1.404(4)
C3 H3A 0.9500
C4 C13 1.413(4)
C4 C5 1.433(4)
C5 C6 1.342(5)
C5 H5A 0.9500
C6 C7 1.429(4)
C6 H6A 0.9500
C7 C8 1.408(4)
C7 C12 1.426(4)
C8 C9 1.363(4)
C8 H8A 0.9500
C9 C10 1.403(4)
C9 H9A 0.9500
C10 C11 1.373(4)
C10 H10A 0.9500
C11 C12 1.423(4)
C12 C13 1.453(4)
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
F1 B1 1.396(4)
F2 B1 1.376(4)
F3 B1 1.361(4)
F4 B1 1.392(4)
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
C13 N1 C1 C2 -0.1(4)
N1 C1 C2 C3 1.6(5)
C1 C2 C3 C4 -1.1(5)
C2 C3 C4 C13 -0.9(4)
C2 C3 C4 C5 180.0(3)
C3 C4 C5 C6 178.2(3)
C13 C4 C5 C6 -0.9(5)
C4 C5 C6 C7 -0.1(5)
C5 C6 C7 C8 -179.8(3)
C5 C6 C7 C12 0.7(5)
C12 C7 C8 C9 -0.9(4)
C6 C7 C8 C9 179.6(3)
C7 C8 C9 C10 0.2(5)
C8 C9 C10 C11 1.0(4)
C9 C10 C11 C12 -1.4(4)
C9 C10 C11 N2 -179.4(3)
C15 N2 C11 C10 -54.5(4)
C14 N2 C11 C10 72.3(3)
C15 N2 C11 C12 127.4(3)
C14 N2 C11 C12 -105.7(3)
C10 C11 C12 C7 0.7(4)
N2 C11 C12 C7 178.6(2)
C10 C11 C12 C13 -179.1(3)
N2 C11 C12 C13 -1.1(4)
C8 C7 C12 C11 0.5(4)
C6 C7 C12 C11 -180.0(3)
C8 C7 C12 C13 -179.8(2)
C6 C7 C12 C13 -0.3(4)
C1 N1 C13 C4 -2.1(4)
C1 N1 C13 C12 178.2(2)
C3 C4 C13 N1 2.5(4)
C5 C4 C13 N1 -178.3(3)
C3 C4 C13 C12 -177.8(3)
C5 C4 C13 C12 1.4(4)
C11 C12 C13 N1 -1.4(4)
C7 C12 C13 N1 178.9(3)
C11 C12 C13 C4 178.9(3)
C7 C12 C13 C4 -0.8(4)
