#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:08:12 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268883 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060782.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_7060782
loop_
_publ_author_name
'Land, Michael A.'
'Robertson, Katherine N.'
'Ylijoki, Kai E. O.'
'Clyburne, Jason A. C.'
_publ_section_title
;
 Reactivity of 1,3-dichloro-1,3-bis(dimethylamino)-propenium salts with
 primary amines
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13558
_journal_page_last               13570
_journal_paper_doi               10.1039/D1NJ02298A
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C13 H18 N3, F6 P'
_chemical_formula_sum            'C13 H18 F6 N3 P'
_chemical_formula_weight         361.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'dual space'
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8863(12)
_cell_length_b                   10.6006(6)
_cell_length_c                   14.2336(8)
_cell_measurement_reflns_used    9411
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.18
_cell_volume                     2998.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_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  0.0287
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17775
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.868
_diffrn_reflns_theta_min         2.049
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.225
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3748
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0361
_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)+(0.0490P)²+2.7104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3128
_reflns_number_total             3748
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02298a3.cif
_cod_data_source_block           compound11_ML115
_cod_depositor_comments
'Adding full bibliography for 7060780--7060787.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7060782
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.917
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
P1A P 0.33145(7) 0.94357(10) 0.12462(8) 0.0177(3) Uani 0.766(9) 1 d D U P A 1
F1A F 0.30340(17) 0.8566(3) 0.2058(2) 0.0391(7) Uani 0.766(9) 1 d D U P A 1
F2A F 0.36150(19) 1.0329(4) 0.0466(2) 0.0434(7) Uani 0.766(9) 1 d D U P A 1
F3A F 0.36792(17) 0.8245(3) 0.0794(2) 0.0360(6) Uani 0.766(9) 1 d D U P A 1
F4A F 0.29724(16) 1.0626(2) 0.17248(16) 0.0412(6) Uani 0.766(9) 1 d D U P A 1
F5A F 0.26594(10) 0.9165(3) 0.06334(17) 0.0483(7) Uani 0.766(9) 1 d D U P A 1
F6A F 0.39847(10) 0.9694(3) 0.18989(17) 0.0492(7) Uani 0.766(9) 1 d D U P A 1
P1B P 0.3290(4) 0.9438(7) 0.1225(5) 0.060(2) Uani 0.234(9) 1 d D U P A 2
F1B F 0.3114(8) 0.8616(13) 0.2111(8) 0.074(4) Uani 0.234(9) 1 d D U P A 2
F2B F 0.3439(7) 1.0152(13) 0.0253(8) 0.057(3) Uani 0.234(9) 1 d D U P A 2
F3B F 0.3823(7) 0.8364(13) 0.1012(11) 0.065(4) Uani 0.234(9) 1 d D U P A 2
F4B F 0.2746(5) 1.0479(9) 0.1402(12) 0.069(3) Uani 0.234(9) 1 d D U P A 2
F5B F 0.2755(7) 0.8665(11) 0.0601(9) 0.087(3) Uani 0.234(9) 1 d D U P A 2
F6B F 0.3819(6) 1.0196(12) 0.1761(7) 0.094(3) Uani 0.234(9) 1 d D U P A 2
N1 N 0.33438(6) 0.45524(11) 0.12708(8) 0.0235(3) Uani 1 1 d . . . . .
N2 N 0.55230(6) 0.26078(12) 0.11398(9) 0.0256(3) Uani 1 1 d . . . . .
N3 N 0.43055(6) 0.57676(11) 0.13322(8) 0.0216(2) Uani 1 1 d . . . . .
H3N H 0.4072(9) 0.6409(18) 0.1346(13) 0.032 Uiso 1 1 d . U . . .
C1 C 0.40164(7) 0.46131(13) 0.12545(9) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.44378(7) 0.35523(13) 0.11961(9) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.423968 0.273737 0.116090 0.026 Uiso 1 1 calc R U . . .
C3 C 0.51361(7) 0.36569(13) 0.11882(9) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.29386(7) 0.56760(14) 0.14467(11) 0.0280(3) Uani 1 1 d . . . . .
H4A H 0.312808 0.612514 0.199663 0.042 Uiso 1 1 calc R U . . .
H4B H 0.247515 0.542316 0.156460 0.042 Uiso 1 1 calc R U . . .
H4C H 0.294141 0.623161 0.089653 0.042 Uiso 1 1 calc R U . . .
C5 C 0.29699(7) 0.33881(14) 0.10869(11) 0.0280(3) Uani 1 1 d . . . . .
H5A H 0.325583 0.278733 0.076278 0.042 Uiso 1 1 calc R U . . .
H5B H 0.256866 0.357274 0.069102 0.042 Uiso 1 1 calc R U . . .
H5C H 0.283403 0.302248 0.168344 0.042 Uiso 1 1 calc R U . . .
C6 C 0.52078(8) 0.13875(14) 0.09374(12) 0.0320(3) Uani 1 1 d . . . . .
H6A H 0.501337 0.105523 0.151004 0.048 Uiso 1 1 calc R U . . .
H6B H 0.554698 0.079699 0.071677 0.048 Uiso 1 1 calc R U . . .
H6C H 0.485187 0.149218 0.044970 0.048 Uiso 1 1 calc R U . . .
C7 C 0.62018(7) 0.24845(16) 0.15793(11) 0.0326(3) Uani 1 1 d . . . . .
H7A H 0.653387 0.242790 0.108860 0.049 Uiso 1 1 calc R U . . .
H7B H 0.622329 0.172031 0.196669 0.049 Uiso 1 1 calc R U . . .
H7C H 0.629961 0.322317 0.197493 0.049 Uiso 1 1 calc R U . . .
C8 C 0.49946(7) 0.59550(13) 0.13080(9) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.52335(7) 0.72007(14) 0.13681(10) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.492988 0.787873 0.145658 0.032 Uiso 1 1 calc R U . . .
C10 C 0.59100(8) 0.74306(15) 0.12980(11) 0.0317(3) Uani 1 1 d . . . . .
H10 H 0.607847 0.826631 0.135862 0.038 Uiso 1 1 calc R U . . .
C11 C 0.63481(8) 0.64333(16) 0.11376(11) 0.0315(3) Uani 1 1 d . . . . .
H11 H 0.681297 0.659964 0.106631 0.038 Uiso 1 1 calc R U . . .
C12 C 0.61170(7) 0.52113(15) 0.10809(10) 0.0274(3) Uani 1 1 d . . . . .
H12 H 0.642247 0.454855 0.095523 0.033 Uiso 1 1 calc R U . . .
C13 C 0.54299(7) 0.49271(13) 0.12073(9) 0.0219(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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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
F5A P1A F2A 92.64(15) . . ?
F5A P1A F1A 89.55(17) . . ?
F2A P1A F1A 177.7(2) . . ?
F5A P1A F4A 91.35(12) . . ?
F2A P1A F4A 90.21(18) . . ?
F1A P1A F4A 89.00(14) . . ?
F5A P1A F3A 90.64(15) . . ?
F2A P1A F3A 90.12(19) . . ?
F1A P1A F3A 90.59(17) . . ?
F4A P1A F3A 177.96(16) . . ?
F5A P1A F6A 178.63(14) . . ?
F2A P1A F6A 88.73(15) . . ?
F1A P1A F6A 89.09(17) . . ?
F4A P1A F6A 88.65(11) . . ?
F3A P1A F6A 89.35(14) . . ?
F6B P1B F4B 90.9(6) . . ?
F6B P1B F1B 93.4(8) . . ?
F4B P1B F1B 94.9(8) . . ?
F6B P1B F5B 176.4(8) . . ?
F4B P1B F5B 90.1(6) . . ?
F1B P1B F5B 89.9(8) . . ?
F6B P1B F3B 91.1(7) . . ?
F4B P1B F3B 177.9(8) . . ?
F1B P1B F3B 85.7(8) . . ?
F5B P1B F3B 87.9(6) . . ?
F6B P1B F2B 92.2(7) . . ?
F4B P1B F2B 87.6(8) . . ?
F1B P1B F2B 173.9(9) . . ?
F5B P1B F2B 84.4(7) . . ?
F3B P1B F2B 91.6(8) . . ?
C1 N1 C5 122.68(12) . . ?
C1 N1 C4 121.29(12) . . ?
C5 N1 C4 116.00(11) . . ?
C3 N2 C6 119.73(12) . . ?
C3 N2 C7 124.36(12) . . ?
C6 N2 C7 112.65(12) . . ?
C1 N3 C8 122.97(12) . . ?
C1 N3 H3N 120.7(13) . . ?
C8 N3 H3N 116.1(13) . . ?
N1 C1 N3 117.57(12) . . ?
N1 C1 C2 124.03(12) . . ?
N3 C1 C2 118.37(12) . . ?
C3 C2 C1 122.19(13) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
N2 C3 C2 120.18(13) . . ?
N2 C3 C13 121.83(12) . . ?
C2 C3 C13 117.97(12) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C13 120.37(12) . . ?
N3 C8 C9 117.75(13) . . ?
C13 C8 C9 121.86(13) . . ?
C10 C9 C8 119.48(14) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.77(14) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.94(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.96(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 116.71(13) . . ?
C8 C13 C3 117.91(12) . . ?
C12 C13 C3 125.29(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
P1A F5A 1.568(2) . ?
P1A F2A 1.592(3) . ?
P1A F1A 1.595(2) . ?
P1A F4A 1.597(2) . ?
P1A F3A 1.603(3) . ?
P1A F6A 1.621(2) . ?
P1B F6B 1.510(9) . ?
P1B F4B 1.571(9) . ?
P1B F1B 1.583(11) . ?
P1B F5B 1.589(10) . ?
P1B F3B 1.592(11) . ?
P1B F2B 1.613(11) . ?
N1 C1 1.3401(17) . ?
N1 C5 1.4599(17) . ?
N1 C4 1.4647(17) . ?
N2 C3 1.3554(17) . ?
N2 C6 1.4616(19) . ?
N2 C7 1.4732(18) . ?
N3 C1 1.3549(17) . ?
N3 C8 1.3863(18) . ?
N3 H3N 0.824(19) . ?
C1 C2 1.4066(19) . ?
C2 C3 1.3937(19) . ?
C2 H2 0.9500 . ?
C3 C13 1.4676(19) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.402(2) . ?
C8 C9 1.4050(19) . ?
C9 C10 1.374(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.4168(19) . ?
C12 H12 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3N F3A^a 0.824(19) 2.230(19) 2.994(4) 154.5(17) . yes
N3 H3N F3B^b 0.824(19) 2.18(2) 2.945(12) 154.6(17) . yes
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
C5 N1 C1 N3 172.85(12) . . . . ?
C4 N1 C1 N3 -5.1(2) . . . . ?
C5 N1 C1 C2 -9.5(2) . . . . ?
C4 N1 C1 C2 172.50(13) . . . . ?
C8 N3 C1 N1 -178.83(12) . . . . ?
C8 N3 C1 C2 3.4(2) . . . . ?
N1 C1 C2 C3 -179.50(12) . . . . ?
N3 C1 C2 C3 -1.9(2) . . . . ?
C6 N2 C3 C2 10.3(2) . . . . ?
C7 N2 C3 C2 -147.83(14) . . . . ?
C6 N2 C3 C13 -168.01(13) . . . . ?
C7 N2 C3 C13 33.9(2) . . . . ?
C1 C2 C3 N2 179.39(13) . . . . ?
C1 C2 C3 C13 -2.3(2) . . . . ?
C1 N3 C8 C13 -0.5(2) . . . . ?
C1 N3 C8 C9 178.19(13) . . . . ?
N3 C8 C9 C10 -176.67(13) . . . . ?
C13 C8 C9 C10 2.0(2) . . . . ?
C8 C9 C10 C11 2.1(2) . . . . ?
C9 C10 C11 C12 -2.3(2) . . . . ?
C10 C11 C12 C13 -1.6(2) . . . . ?
N3 C8 C13 C12 172.98(12) . . . . ?
C9 C8 C13 C12 -5.7(2) . . . . ?
N3 C8 C13 C3 -3.71(19) . . . . ?
C9 C8 C13 C3 177.62(13) . . . . ?
C11 C12 C13 C8 5.4(2) . . . . ?
C11 C12 C13 C3 -178.14(13) . . . . ?
N2 C3 C13 C8 -176.69(12) . . . . ?
C2 C3 C13 C8 4.99(18) . . . . ?
N2 C3 C13 C12 6.9(2) . . . . ?
C2 C3 C13 C12 -171.38(13) . . . . ?
