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#$Date: 2021-09-06 15:08:12 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268883 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060786.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_7060786
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         'C11 H22 N3, F6 P'
_chemical_formula_sum            'C11 H22 F6 N3 P'
_chemical_formula_weight         341.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 113.5370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7611(9)
_cell_length_b                   10.3655(8)
_cell_length_c                   14.2459(11)
_cell_measurement_reflns_used    9930
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.51
_cell_volume                     1592.2(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.943
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18685
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.891
_diffrn_reflns_theta_min         1.910
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       'thick rod'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.275
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0351
_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)+(0.0595P)²+0.5325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3336
_reflns_number_total             3940
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02298a3.cif
_cod_data_source_block           compound8c_ML150
_cod_depositor_comments
'Adding full bibliography for 7060780--7060787.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7060786
_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   0.884
_shelx_estimated_absorpt_t_max   0.939
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
P1 P 0.02091(3) 0.31185(3) 0.29476(3) 0.02225(11) Uani 1 1 d . . . . .
F1 F 0.00432(9) 0.16896(8) 0.32954(7) 0.0345(2) Uani 1 1 d . . . . .
F2 F 0.03734(8) 0.45555(9) 0.25982(8) 0.0398(2) Uani 1 1 d . . . . .
F3 F -0.12223(8) 0.31536(10) 0.21814(8) 0.0430(3) Uani 1 1 d . . . . .
F4 F 0.16362(9) 0.31021(9) 0.37038(9) 0.0452(3) Uani 1 1 d . . . . .
F5 F -0.01478(11) 0.37000(10) 0.38300(8) 0.0449(3) Uani 1 1 d . . . . .
F6 F 0.05594(11) 0.25428(10) 0.20568(8) 0.0478(3) Uani 1 1 d . . . . .
N1 N 0.63998(11) 0.40693(11) 0.44109(9) 0.0262(2) Uani 1 1 d . . . . .
N2 N 0.33070(10) 0.08170(11) 0.39227(8) 0.0219(2) Uani 1 1 d . . . . .
N3 N 0.53358(10) 0.31436(10) 0.28154(8) 0.0218(2) Uani 1 1 d . . . . .
C1 C 0.55680(12) 0.32068(12) 0.38533(10) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.48703(12) 0.24565(12) 0.42575(10) 0.0216(3) Uani 1 1 d . . . . .
H2 H 0.499190 0.255375 0.495422 0.026 Uiso 1 1 calc R U . . .
C3 C 0.40080(12) 0.15781(12) 0.36410(10) 0.0201(2) Uani 1 1 d . . . . .
H3 H 0.391418 0.152002 0.294839 0.024 Uiso 1 1 calc R U . . .
C4 C 0.70835(15) 0.48926(15) 0.39736(12) 0.0339(3) Uani 1 1 d . . . . .
H4A H 0.781352 0.442778 0.398285 0.051 Uiso 1 1 calc R U . . .
H4B H 0.734840 0.568333 0.438035 0.051 Uiso 1 1 calc R U . . .
H4C H 0.654430 0.511525 0.326631 0.051 Uiso 1 1 calc R U . . .
C5 C 0.67002(15) 0.42306(15) 0.55075(11) 0.0326(3) Uani 1 1 d . . . . .
H5A H 0.599002 0.461363 0.559984 0.049 Uiso 1 1 calc R U . . .
H5B H 0.742198 0.479860 0.580899 0.049 Uiso 1 1 calc R U . . .
H5C H 0.688945 0.338746 0.584614 0.049 Uiso 1 1 calc R U . . .
C6 C 0.33387(14) 0.08583(15) 0.49571(10) 0.0293(3) Uani 1 1 d . . . . .
H6A H 0.410148 0.044727 0.543329 0.044 Uiso 1 1 calc R U . . .
H6B H 0.261852 0.039725 0.497180 0.044 Uiso 1 1 calc R U . . .
H6C H 0.331747 0.175804 0.516074 0.044 Uiso 1 1 calc R U . . .
C7 C 0.24388(13) -0.00916(14) 0.32106(11) 0.0267(3) Uani 1 1 d . . . . .
H7A H 0.250839 -0.004540 0.254845 0.040 Uiso 1 1 calc R U . . .
H7B H 0.159105 0.012925 0.311992 0.040 Uiso 1 1 calc R U . . .
H7C H 0.263431 -0.096849 0.348537 0.040 Uiso 1 1 calc R U . . .
C8 C 0.59554(12) 0.23871(12) 0.24860(10) 0.0211(3) Uani 1 1 d . . . . .
C9 C 0.69787(13) 0.15141(14) 0.31441(11) 0.0264(3) Uani 1 1 d . . . . .
H9A H 0.707809 0.159130 0.385834 0.040 Uiso 1 1 calc R U . . .
H9B H 0.775411 0.176005 0.308871 0.040 Uiso 1 1 calc R U . . .
H9C H 0.677311 0.062006 0.291562 0.040 Uiso 1 1 calc R U . . .
C10 C 0.56723(13) 0.23662(14) 0.13601(10) 0.0262(3) Uani 1 1 d . . . . .
H10A H 0.540173 0.148483 0.109850 0.031 Uiso 1 1 calc R U . . .
H10B H 0.644757 0.254798 0.126766 0.031 Uiso 1 1 calc R U . . .
C11 C 0.46909(16) 0.33107(17) 0.07154(11) 0.0388(4) Uani 1 1 d . . . . .
H11A H 0.389050 0.307581 0.072905 0.058 Uiso 1 1 calc R U . . .
H11B H 0.462678 0.328494 0.000835 0.058 Uiso 1 1 calc R U . . .
H11C H 0.491953 0.418332 0.099118 0.058 Uiso 1 1 calc R U . . .
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
F4 P1 F5 90.51(6) . . ?
F4 P1 F6 89.82(6) . . ?
F5 P1 F6 179.56(6) . . ?
F4 P1 F1 90.38(5) . . ?
F5 P1 F1 90.16(5) . . ?
F6 P1 F1 90.13(5) . . ?
F4 P1 F3 179.21(6) . . ?
F5 P1 F3 89.58(6) . . ?
F6 P1 F3 90.08(6) . . ?
F1 P1 F3 90.40(5) . . ?
F4 P1 F2 89.70(5) . . ?
F5 P1 F2 89.76(6) . . ?
F6 P1 F2 89.95(6) . . ?
F1 P1 F2 179.89(6) . . ?
F3 P1 F2 89.52(5) . . ?
C1 N1 C5 121.32(12) . . ?
C1 N1 C4 122.25(12) . . ?
C5 N1 C4 116.42(12) . . ?
C3 N2 C6 121.62(11) . . ?
C3 N2 C7 121.67(11) . . ?
C6 N2 C7 116.70(11) . . ?
C8 N3 C1 121.23(11) . . ?
N1 C1 N3 116.83(11) . . ?
N1 C1 C2 122.45(12) . . ?
N3 C1 C2 120.53(12) . . ?
C3 C2 C1 120.14(11) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
N2 C3 C2 126.22(12) . . ?
N2 C3 H3 116.9 . . ?
C2 C3 H3 116.9 . . ?
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 C9 124.97(12) . . ?
N3 C8 C10 118.96(12) . . ?
C9 C8 C10 116.07(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 C11 115.40(11) . . ?
C8 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
C8 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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
P1 F4 1.5918(9) . ?
P1 F5 1.5940(10) . ?
P1 F6 1.5980(10) . ?
P1 F1 1.5983(9) . ?
P1 F3 1.5998(10) . ?
P1 F2 1.6063(9) . ?
N1 C1 1.3291(17) . ?
N1 C5 1.4671(17) . ?
N1 C4 1.4707(18) . ?
N2 C3 1.3144(16) . ?
N2 C6 1.4597(16) . ?
N2 C7 1.4599(17) . ?
N3 C8 1.2803(17) . ?
N3 C1 1.3938(16) . ?
C1 C2 1.4096(18) . ?
C2 C3 1.3847(18) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
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 C9 1.4983(19) . ?
C8 C10 1.5025(17) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.512(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
_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 179.03(12) . . . . ?
C4 N1 C1 N3 -2.16(19) . . . . ?
C5 N1 C1 C2 4.1(2) . . . . ?
C4 N1 C1 C2 -177.08(13) . . . . ?
C8 N3 C1 N1 90.47(15) . . . . ?
C8 N3 C1 C2 -94.50(16) . . . . ?
N1 C1 C2 C3 179.49(12) . . . . ?
N3 C1 C2 C3 4.75(19) . . . . ?
C6 N2 C3 C2 2.4(2) . . . . ?
C7 N2 C3 C2 -179.00(12) . . . . ?
C1 C2 C3 N2 179.49(12) . . . . ?
C1 N3 C8 C9 -0.6(2) . . . . ?
C1 N3 C8 C10 -179.52(11) . . . . ?
N3 C8 C10 C11 2.55(19) . . . . ?
C9 C8 C10 C11 -176.46(13) . . . . ?
