#------------------------------------------------------------------------------
#$Date: 2025-08-20 12:41:31 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301828 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/59/4035956.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_4035956
loop_
_publ_author_name
'Pozharskii, Alexander F.'
'Ozeryanskii, Valery A.'
'Filatova, Ekaterina A.'
'Dyablo, Olga V.'
'Pogosova, Olga G.'
'Borodkin, Gennady S.'
'Filarowski, Aleksander'
'Steglenko, Dmitriy V.'
_publ_section_title
;
 Neutral Pyrrole Nitrogen Atom as a π- and Mixed n,π-Donor in Hydrogen
 Bonding.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              726
_journal_page_last               737
_journal_paper_doi               10.1021/acs.joc.8b02562
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H18 N+, B F4-'
_chemical_formula_sum            'C18 H18 B F4 N'
_chemical_formula_weight         335.14
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.176(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9334(13)
_cell_length_b                   11.7951(12)
_cell_length_c                   10.7132(11)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.35
_cell_volume                     1608.6(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.1176
_diffrn_reflns_av_sigmaI/netI    0.1042
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17653
_diffrn_reflns_theta_full        28.02
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colorless
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.1421
_refine_ls_R_factor_gt           0.0492
_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)+(0.0467P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                1900
_reflns_number_total             3887
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo8b02562_si_008.cif
_cod_data_source_block           s30
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               4035956
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
B1 B 0.8231(2) 0.4047(2) 0.1616(3) 0.0267(6) Uani 1 1 d .
F1 F 0.74898(11) 0.48934(11) 0.12427(13) 0.0375(4) Uani 1 1 d .
F2 F 0.80276(11) 0.35474(11) 0.27219(12) 0.0361(4) Uani 1 1 d .
F3 F 0.92189(11) 0.45354(13) 0.18242(14) 0.0498(4) Uani 1 1 d .
F4 F 0.81507(12) 0.32503(12) 0.06496(13) 0.0477(4) Uani 1 1 d .
N1 N 0.77850(15) -0.01941(15) 0.24496(18) 0.0222(4) Uani 1 1 d .
H1 H 0.7980(15) -0.0591(16) 0.1798(19) 0.015(6) Uiso 1 1 d .
C1 C 0.60105(16) -0.09790(17) 0.14284(19) 0.0190(5) Uani 1 1 d .
C2 C 0.66337(17) -0.02930(17) 0.2378(2) 0.0210(5) Uani 1 1 d .
C3 C 0.62222(18) 0.02942(19) 0.3276(2) 0.0274(6) Uani 1 1 d .
H3A H 0.6668 0.0740 0.3885 0.033 Uiso 1 1 calc R
C4 C 0.51440(18) 0.0239(2) 0.3296(2) 0.0301(6) Uani 1 1 d .
H4A H 0.4856 0.0650 0.3916 0.036 Uiso 1 1 calc R
C5 C 0.45108(18) -0.04049(19) 0.2428(2) 0.0274(6) Uani 1 1 d .
H5A H 0.3783 -0.0451 0.2460 0.033 Uiso 1 1 calc R
C6 C 0.49097(17) -0.10064(18) 0.1479(2) 0.0222(5) Uani 1 1 d .
C7 C 0.42205(18) -0.16437(18) 0.0576(2) 0.0272(6) Uani 1 1 d .
H7A H 0.3496 -0.1679 0.0631 0.033 Uiso 1 1 calc R
C8 C 0.45747(18) -0.22094(19) -0.0372(2) 0.0309(6) Uani 1 1 d .
H8A H 0.4098 -0.2612 -0.0992 0.037 Uiso 1 1 calc R
C9 C 0.56561(18) -0.21918(18) -0.0427(2) 0.0277(6) Uani 1 1 d .
H9A H 0.5898 -0.2592 -0.1089 0.033 Uiso 1 1 calc R
C10 C 0.63706(17) -0.16168(17) 0.04443(19) 0.0203(5) Uani 1 1 d .
C11 C 0.75050(17) -0.17116(17) 0.03367(19) 0.0201(5) Uani 1 1 d .
C12 C 0.81483(18) -0.24999(18) 0.1078(2) 0.0255(5) Uani 1 1 d .
H12A H 0.7857 -0.2995 0.1624 0.031 Uiso 1 1 calc R
C13 C 0.92070(19) -0.2563(2) 0.1021(2) 0.0311(6) Uani 1 1 d .
H13A H 0.9638 -0.3098 0.1534 0.037 Uiso 1 1 calc R
C14 C 0.96427(19) -0.1859(2) 0.0226(2) 0.0321(6) Uani 1 1 d .
H14A H 1.0373 -0.1898 0.0203 0.039 Uiso 1 1 calc R
C15 C 0.90091(18) -0.1094(2) -0.0537(2) 0.0298(6) Uani 1 1 d .
H15A H 0.9303 -0.0620 -0.1101 0.036 Uiso 1 1 calc R
C16 C 0.79469(18) -0.10182(18) -0.0483(2) 0.0251(5) Uani 1 1 d .
H16A H 0.7518 -0.0490 -0.1009 0.030 Uiso 1 1 calc R
C17 C 0.81454(19) 0.09940(19) 0.2295(3) 0.0379(6) Uani 1 1 d .
H17A H 0.7732 0.1326 0.1528 0.057 Uiso 1 1 calc R
H17B H 0.8890 0.0989 0.2223 0.057 Uiso 1 1 calc R
H17C H 0.8050 0.1445 0.3035 0.057 Uiso 1 1 calc R
C18 C 0.83861(18) -0.0746(2) 0.3620(2) 0.0322(6) Uani 1 1 d .
H18A H 0.8170 -0.1540 0.3650 0.048 Uiso 1 1 calc R
H18B H 0.8241 -0.0348 0.4373 0.048 Uiso 1 1 calc R
H18C H 0.9140 -0.0710 0.3601 0.048 Uiso 1 1 calc R
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
F3 B1 F4 110.3(2)
F3 B1 F2 110.3(2)
F4 B1 F2 110.4(2)
F3 B1 F1 108.5(2)
F4 B1 F1 108.3(2)
F2 B1 F1 108.9(2)
C2 N1 C17 113.45(18)
C2 N1 C18 112.11(17)
C17 N1 C18 111.90(18)
C2 N1 H1 109.3(13)
C17 N1 H1 105.2(12)
C18 N1 H1 104.1(12)
C2 C1 C6 115.09(19)
C2 C1 C10 127.01(19)
C6 C1 C10 117.89(19)
C3 C2 C1 123.1(2)
C3 C2 N1 115.9(2)
C1 C2 N1 121.05(19)
C2 C3 C4 120.0(2)
C2 C3 H3A 120.0
C4 C3 H3A 120.0
C5 C4 C3 119.8(2)
C5 C4 H4A 120.1
C3 C4 H4A 120.1
C4 C5 C6 121.5(2)
C4 C5 H5A 119.3
C6 C5 H5A 119.3
C5 C6 C7 119.7(2)
C5 C6 C1 120.5(2)
C7 C6 C1 119.8(2)
C8 C7 C6 121.2(2)
C8 C7 H7A 119.4
C6 C7 H7A 119.4
C7 C8 C9 119.4(2)
C7 C8 H8A 120.3
C9 C8 H8A 120.3
C10 C9 C8 122.2(2)
C10 C9 H9A 118.9
C8 C9 H9A 118.9
C9 C10 C1 119.4(2)
C9 C10 C11 117.57(19)
C1 C10 C11 123.00(18)
C16 C11 C12 118.6(2)
C16 C11 C10 121.43(19)
C12 C11 C10 119.96(19)
C13 C12 C11 120.4(2)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C14 C13 C12 120.7(2)
C14 C13 H13A 119.7
C12 C13 H13A 119.7
C13 C14 C15 119.6(2)
C13 C14 H14A 120.2
C15 C14 H14A 120.2
C14 C15 C16 120.3(2)
C14 C15 H15A 119.9
C16 C15 H15A 119.9
C15 C16 C11 120.5(2)
C15 C16 H16A 119.8
C11 C16 H16A 119.8
N1 C17 H17A 109.5
N1 C17 H17B 109.5
H17A C17 H17B 109.5
N1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
N1 C18 H18A 109.5
N1 C18 H18B 109.5
H18A C18 H18B 109.5
N1 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F3 1.383(3)
B1 F4 1.389(3)
B1 F2 1.390(3)
B1 F1 1.392(3)
N1 C2 1.482(3)
N1 C17 1.495(3)
N1 C18 1.502(3)
N1 H1 0.91(2)
C1 C2 1.431(3)
C1 C6 1.435(3)
C1 C10 1.438(3)
C2 C3 1.367(3)
C3 C4 1.400(3)
C3 H3A 0.9500
C4 C5 1.358(3)
C4 H4A 0.9500
C5 C6 1.410(3)
C5 H5A 0.9500
C6 C7 1.411(3)
C7 C8 1.361(3)
C7 H7A 0.9500
C8 C9 1.410(3)
C8 H8A 0.9500
C9 C10 1.371(3)
C9 H9A 0.9500
C10 C11 1.496(3)
C11 C16 1.394(3)
C11 C12 1.398(3)
C12 C13 1.383(3)
C12 H12A 0.9500
C13 C14 1.379(3)
C13 H13A 0.9500
C14 C15 1.385(3)
C14 H14A 0.9500
C15 C16 1.388(3)
C15 H15A 0.9500
C16 H16A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
C6 C1 C2 C3 0.3(3)
C10 C1 C2 C3 179.5(2)
C6 C1 C2 N1 179.36(18)
C10 C1 C2 N1 -1.4(3)
C17 N1 C2 C3 -60.8(3)
C18 N1 C2 C3 67.2(2)
C17 N1 C2 C1 120.0(2)
C18 N1 C2 C1 -112.0(2)
C1 C2 C3 C4 0.1(3)
N1 C2 C3 C4 -179.01(19)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 -1.4(3)
C4 C5 C6 C7 -178.5(2)
C4 C5 C6 C1 1.8(3)
C2 C1 C6 C5 -1.2(3)
C10 C1 C6 C5 179.52(19)
C2 C1 C6 C7 179.11(19)
C10 C1 C6 C7 -0.2(3)
C5 C6 C7 C8 178.2(2)
C1 C6 C7 C8 -2.1(3)
C6 C7 C8 C9 2.3(3)
C7 C8 C9 C10 -0.3(3)
C8 C9 C10 C1 -1.9(3)
C8 C9 C10 C11 176.6(2)
C2 C1 C10 C9 -177.1(2)
C6 C1 C10 C9 2.1(3)
C2 C1 C10 C11 4.5(3)
C6 C1 C10 C11 -176.32(19)
C9 C10 C11 C16 84.1(3)
C1 C10 C11 C16 -97.5(2)
C9 C10 C11 C12 -96.6(2)
C1 C10 C11 C12 81.8(3)
C16 C11 C12 C13 1.8(3)
C10 C11 C12 C13 -177.5(2)
C11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 -1.1(3)
C13 C14 C15 C16 1.5(3)
C14 C15 C16 C11 -0.2(3)
C12 C11 C16 C15 -1.5(3)
C10 C11 C16 C15 177.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168329601
