#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/78/2207817.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207817
loop_
_publ_author_name
'Rozycka-Sokolowska, Ewa'
'Girek, Tomasz'
'Marciniak, Bernard'
'Pavlyuk, Volodymyr'
_publ_section_title
;
 1-(N,N-Diethylamino)-2,3-diphenylcyclopropenylium
 tetrafluoroborate
;
_journal_coeditor_code           KP6073
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o274
_journal_page_last               o275
_journal_paper_doi               10.1107/S1600536805041814
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H20 N +, B F4 -'
_chemical_formula_moiety         'C19 H20 N +, B F4 -'
_chemical_formula_sum            'C19 H20 B F4 N'
_chemical_formula_weight         349.17
_chemical_name_systematic
;
1-(N,N-Diethylamino)-2,3-diphenylcyclopropenylium tetrafluoroborate
;
_space_group_IT_number           14
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.216(3)
_cell_length_b                   8.004(2)
_cell_length_c                   18.5010(10)
_cell_measurement_reflns_used    30
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      5
_cell_volume                     1800.8(8)
_computing_cell_refinement       'DARCH Package'
_computing_data_collection       'DARCH Package (Burevestnik, 1991)'
_computing_data_reduction        'DARCH Package'
_computing_molecular_graphics    'ORTEP-3 (Farrugia,1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  DARCH-1
_diffrn_measurement_method       'w-2theta scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'BSW x-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4116
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        2.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  .997
_exptl_absorpt_correction_T_min  .979
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(DIFABS; Walker & Stuart,1983)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0378
_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)+(0.0553P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2076
_reflns_number_total             4116
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp6073.cif
_cod_data_source_block           I
_cod_original_cell_volume        1800.9(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207817
_cod_database_fobs_code          2207817
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
N1 0.30027(10) -0.01960(16) 0.09064(8) 0.0956(3) Uani d . 1 N
F1 0.29763(11) 0.42283(19) 0.10553(8) 0.1647(5) Uani d . 1 F
F2 0.23338(12) 0.58715(16) 0.16939(9) 0.1581(5) Uani d . 1 F
F3 0.15700(11) 0.34008(18) 0.11690(9) 0.1723(6) Uani d . 1 F
F4 0.32390(12) 0.35936(18) 0.23299(9) 0.1663(5) Uani d . 1 F
B1 0.2528(2) 0.4276(3) 0.15461(18) 0.1312(7) Uani d . 1 B
C1 0.38796(12) 0.15154(17) 0.02016(9) 0.0902(4) Uani d . 1 C
C2 0.27902(12) 0.17673(18) -0.02842(9) 0.0910(4) Uani d . 1 C
C3 0.31844(12) 0.07670(18) 0.04246(9) 0.0906(4) Uani d . 1 C
C4 0.39081(14) -0.1018(2) 0.16554(10) 0.1054(5) Uani d . 1 C
H4A 0.4552 -0.1043 0.1603 0.156(4) Uiso calc R 1 H
H4B 0.3702 -0.2163 0.1677 0.156(4) Uiso calc R 1 H
C5 0.41936(16) -0.0166(3) 0.24561(11) 0.1329(6) Uani d . 1 C
H5A 0.4390 0.0974 0.2437 0.170(3) Uiso calc R 1 H
H5B 0.4803 -0.0727 0.2922 0.170(3) Uiso calc R 1 H
H5C 0.3572 -0.0192 0.2528 0.170(3) Uiso calc R 1 H
C6 0.18597(13) -0.0468(2) 0.07090(11) 0.1075(5) Uani d . 1 C
H6A 0.1884 -0.0962 0.1197 0.156(4) Uiso calc R 1 H
H6B 0.1494 0.0605 0.0603 0.156(4) Uiso calc R 1 H
C7 0.12173(14) -0.1547(3) -0.00214(12) 0.1311(7) Uani d . 1 C
H7A 0.1124 -0.1012 -0.0519 0.170(3) Uiso calc R 1 H
H7B 0.0510 -0.1750 -0.0090 0.170(3) Uiso calc R 1 H
H7C 0.1595 -0.2589 0.0064 0.170(3) Uiso calc R 1 H
C8 0.49724(12) 0.19413(17) 0.03963(9) 0.0884(4) Uani d . 1 C
C9 0.58897(13) 0.1518(2) 0.11714(10) 0.1013(4) Uani d . 1 C
H9 0.5807 0.0869 0.1552 0.144(2) Uiso calc R 1 H
C10 0.69187(14) 0.2058(2) 0.13773(12) 0.1121(5) Uani d . 1 C
H10 0.7528 0.1788 0.1900 0.144(2) Uiso calc R 1 H
C11 0.70464(15) 0.2987(2) 0.08153(13) 0.1119(5) Uani d . 1 C
H11 0.7744 0.3349 0.0959 0.144(2) Uiso calc R 1 H
C12 0.61567(17) 0.3394(2) 0.00420(13) 0.1137(5) Uani d . 1 C
H12 0.6250 0.4015 -0.0341 0.144(2) Uiso calc R 1 H
C13 0.51191(14) 0.2872(2) -0.01647(11) 0.1025(4) Uani d . 1 C
H13 0.4514 0.3153 -0.0688 0.144(2) Uiso calc R 1 H
C14 0.18897(11) 0.26034(19) -0.10059(9) 0.0895(4) Uani d . 1 C
C15 0.19179(13) 0.2839(2) -0.17372(9) 0.0998(4) Uani d . 1 C
H15 0.2515 0.2459 -0.1767 0.144(2) Uiso calc R 1 H
C16 0.10669(15) 0.3629(2) -0.24119(11) 0.1141(5) Uani d . 1 C
H16 0.1077 0.3764 -0.2907 0.144(2) Uiso calc R 1 H
C17 0.02026(15) 0.4222(2) -0.23651(11) 0.1211(6) Uani d . 1 C
H17 -0.0369 0.4768 -0.2829 0.144(2) Uiso calc R 1 H
C18 0.01606(14) 0.4031(2) -0.16545(12) 0.1192(6) Uani d . 1 C
H18 -0.0428 0.4462 -0.1628 0.144(2) Uiso calc R 1 H
C19 0.09981(13) 0.3190(2) -0.09676(10) 0.1049(5) Uani d . 1 C
H19 0.0963 0.3021 -0.0485 0.144(2) Uiso calc R 1 H
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'
B B 0.0013 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 N1 C4 . . 121.53(13)
C3 N1 C6 . . 119.89(13)
C4 N1 C6 . . 118.57(13)
F3 F3 B1 1 . 0(10)
F1 B1 F3 . 1 109.6(2)
F1 B1 F3 . . 109.6(2)
F3 B1 F3 1 . 0.00(16)
F1 B1 F2 . . 112.0(2)
F3 B1 F2 1 . 109.4(2)
F3 B1 F2 . . 109.4(2)
F1 B1 F4 . . 110.5(2)
F3 B1 F4 1 . 109.2(2)
F3 B1 F4 . . 109.2(2)
F2 B1 F4 . . 105.9(2)
C2 C1 C3 . . 60.82(11)
C2 C1 C8 . . 148.32(14)
C3 C1 C8 . . 150.25(14)
C1 C2 C3 . . 61.20(11)
C1 C2 C14 . . 148.01(14)
C3 C2 C14 . . 150.67(14)
N1 C3 C2 . . 149.92(15)
N1 C3 C1 . . 152.04(15)
C2 C3 C1 . . 57.99(10)
N1 C4 C5 . . 112.87(15)
N1 C4 H4A . . 109.0
C5 C4 H4A . . 109.0
N1 C4 H4B . . 109.0
C5 C4 H4B . . 109.0
H4A C4 H4B . . 107.8
C4 C5 H5A . . 109.5
C4 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C4 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C7 C6 N1 . . 113.26(14)
C7 C6 H6A . . 108.9
N1 C6 H6A . . 108.9
C7 C6 H6B . . 108.9
N1 C6 H6B . . 108.9
H6A C6 H6B . . 107.7
C6 C7 H7A . . 109.5
C6 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C6 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C13 C8 C9 . . 118.76(14)
C13 C8 C1 . . 120.22(14)
C9 C8 C1 . . 120.90(14)
C10 C9 C8 . . 120.25(16)
C10 C9 H9 . . 119.9
C8 C9 H9 . . 119.9
C11 C10 C9 . . 120.11(17)
C11 C10 H10 . . 119.9
C9 C10 H10 . . 119.9
C10 C11 C12 . . 120.64(17)
C10 C11 H11 . . 119.7
C12 C11 H11 . . 119.7
C11 C12 C13 . . 119.52(17)
C11 C12 H12 . . 120.2
C13 C12 H12 . . 120.2
C8 C13 C12 . . 120.71(16)
C8 C13 H13 . . 119.6
C12 C13 H13 . . 119.6
C15 C14 C19 . . 119.50(14)
C15 C14 C2 . . 120.24(13)
C19 C14 C2 . . 120.26(13)
C16 C15 C14 . . 119.74(15)
C16 C15 H15 . . 120.1
C14 C15 H15 . . 120.1
C17 C16 C15 . . 120.39(17)
C17 C16 H16 . . 119.8
C15 C16 H16 . . 119.8
C18 C17 C16 . . 121.13(17)
C18 C17 H17 . . 119.4
C16 C17 H17 . . 119.4
C17 C18 C19 . . 119.76(17)
C17 C18 H18 . . 120.1
C19 C18 H18 . . 120.1
C18 C19 C14 . . 119.44(15)
C18 C19 H19 . . 120.3
C14 C19 H19 . . 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C3 . 1.3014(18)
N1 C4 . 1.470(2)
N1 C6 . 1.4855(19)
F1 B1 . 1.354(3)
F2 B1 . 1.364(3)
F3 F3 1 0.000(3)
F3 B1 . 1.359(3)
F4 B1 . 1.380(3)
B1 F3 1 1.359(3)
C1 C2 . 1.344(2)
C1 C3 . 1.388(2)
C1 C8 . 1.442(2)
C2 C3 . 1.383(2)
C2 C14 . 1.449(2)
C4 C5 . 1.484(2)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 0.9600
C6 C7 . 1.459(2)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C13 . 1.379(2)
C8 C9 . 1.391(2)
C9 C10 . 1.376(2)
C9 H9 . 0.9300
C10 C11 . 1.365(2)
C10 H10 . 0.9300
C11 C12 . 1.370(3)
C11 H11 . 0.9300
C12 C13 . 1.383(2)
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 C15 . 1.3870(19)
C14 C19 . 1.388(2)
C15 C16 . 1.363(2)
C15 H15 . 0.9300
C16 C17 . 1.361(3)
C16 H16 . 0.9300
C17 C18 . 1.355(2)
C17 H17 . 0.9300
C18 C19 . 1.385(2)
C18 H18 . 0.9300
C19 H19 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4B F2 1_545 0.97 2.51 3.373(2) 148
C6 H6B F3 1 0.97 2.45 3.293(2) 145
C12 H12 F1 3_665 0.93 2.54 3.443(2) 165
C15 H15 F4 4_565 0.93 2.52 3.343(2) 148
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_site_symmetry_1
_geom_torsion
F3 F3 B1 F1 1 0.00(5)
F3 F3 B1 F2 1 0.00(3)
F3 F3 B1 F4 1 0.00(2)
C8 C1 C2 C3 . -171.3(3)
C3 C1 C2 C14 . 176.1(3)
C8 C1 C2 C14 . 4.8(4)
C4 N1 C3 C2 . 177.9(2)
C6 N1 C3 C2 . -2.8(4)
C4 N1 C3 C1 . 2.5(4)
C6 N1 C3 C1 . -178.2(3)
C1 C2 C3 N1 . -177.5(3)
C14 C2 C3 N1 . 6.8(5)
C14 C2 C3 C1 . -175.8(3)
C2 C1 C3 N1 . 177.3(3)
C8 C1 C3 N1 . -12.0(5)
C8 C1 C3 C2 . 170.7(3)
C3 N1 C4 C5 . 101.73(18)
C6 N1 C4 C5 . -77.56(19)
C3 N1 C6 C7 . 73.2(2)
C4 N1 C6 C7 . -107.45(18)
C2 C1 C8 C13 . -13.4(3)
C3 C1 C8 C13 . -177.8(2)
C2 C1 C8 C9 . 162.5(2)
C3 C1 C8 C9 . -2.0(3)
C13 C8 C9 C10 . 1.5(2)
C1 C8 C9 C10 . -174.36(14)
C8 C9 C10 C11 . -1.1(3)
C9 C10 C11 C12 . -0.1(3)
C10 C11 C12 C13 . 0.8(3)
C9 C8 C13 C12 . -0.7(2)
C1 C8 C13 C12 . 175.15(14)
C11 C12 C13 C8 . -0.4(3)
C1 C2 C14 C15 . 38.2(3)
C3 C2 C14 C15 . -148.8(2)
C1 C2 C14 C19 . -141.1(2)
C3 C2 C14 C19 . 31.9(3)
C19 C14 C15 C16 . -0.6(2)
C2 C14 C15 C16 . -179.92(15)
C14 C15 C16 C17 . 1.5(3)
C15 C16 C17 C18 . -0.6(3)
C16 C17 C18 C19 . -1.3(3)
C17 C18 C19 C14 . 2.2(3)
C15 C14 C19 C18 . -1.2(2)
C2 C14 C19 C18 . 178.08(15)
