#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:08:12 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268883 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/07/7060780.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_7060780
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         'C27 H45 N4, F6 P, C H2 Cl2'
_chemical_formula_sum            'C28 H47 Cl2 F6 N4 P'
_chemical_formula_weight         655.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                95.442(2)
_cell_angle_beta                 100.844(2)
_cell_angle_gamma                111.6480(10)
_cell_formula_units_Z            2
_cell_length_a                   11.1649(14)
_cell_length_b                   11.6494(14)
_cell_length_c                   13.3995(16)
_cell_measurement_reflns_used    6390
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.24
_cell_volume                     1565.0(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 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16587
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.912
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       'rectangualr prism'
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         6139
_refine_ls_number_restraints     266
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0499P)²+0.9122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4474
_reflns_number_total             6139
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02298a3.cif
_cod_data_source_block           compound7a_ML092
_cod_depositor_comments
'Adding full bibliography for 7060780--7060787.cif.'
_cod_database_code               7060780
_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   0.896
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
C28A C 0.517(2) 0.8506(12) 0.3956(11) 0.062(4) Uani 0.462(3) 1 d D U P A 1
H28A H 0.442145 0.878299 0.382804 0.075 Uiso 0.462(3) 1 calc R U P A 1
H28B H 0.549492 0.851836 0.331863 0.075 Uiso 0.462(3) 1 calc R U P A 1
Cl1A Cl 0.6459(3) 0.9634(3) 0.4956(3) 0.0402(7) Uani 0.462(3) 1 d D U P A 1
Cl2A Cl 0.4533(5) 0.6961(5) 0.4139(4) 0.081(2) Uani 0.462(3) 1 d D U P A 1
C28B C 0.5441(16) 0.8547(15) 0.3885(11) 0.046(4) Uani 0.395(3) 1 d D U P B 2
H28C H 0.496715 0.890575 0.338789 0.056 Uiso 0.395(3) 1 calc R U P B 2
H28D H 0.594402 0.817532 0.352374 0.056 Uiso 0.395(3) 1 calc R U P B 2
Cl1B Cl 0.6525(8) 0.9724(8) 0.4945(6) 0.116(3) Uani 0.395(3) 1 d D U P B 2
Cl2B Cl 0.4311(6) 0.7406(5) 0.4389(5) 0.0836(17) Uani 0.395(3) 1 d D U P B 2
C28C C 0.571(5) 0.834(2) 0.390(3) 0.063(6) Uani 0.143(3) 1 d D U P C 3
H28E H 0.542508 0.843176 0.317604 0.076 Uiso 0.143(3) 1 calc R U P C 3
H28F H 0.666156 0.849177 0.403470 0.076 Uiso 0.143(3) 1 calc R U P C 3
Cl1C Cl 0.5527(19) 0.9527(14) 0.4733(11) 0.179(6) Uani 0.143(3) 1 d D U P C 3
Cl2C Cl 0.482(2) 0.6808(19) 0.4030(18) 0.129(6) Uani 0.143(3) 1 d D U P C 3
P1 P 0.67129(6) 0.89493(6) 0.14355(5) 0.02895(16) Uani 1 1 d . . . . .
F1 F 0.80971(14) 0.99666(15) 0.13379(12) 0.0532(4) Uani 1 1 d . . . . .
F2 F 0.53375(13) 0.79367(13) 0.15382(12) 0.0447(4) Uani 1 1 d . . . . .
F3A F 0.7423(16) 0.8470(15) 0.2362(10) 0.039(2) Uani 0.67(5) 1 d D . P D 1
F4A F 0.6040(15) 0.9355(8) 0.0456(10) 0.051(3) Uani 0.67(5) 1 d D . P D 1
F5A F 0.6651(14) 0.9990(12) 0.2188(12) 0.0432(18) Uani 0.67(5) 1 d D . P D 1
F6A F 0.6828(15) 0.7849(13) 0.0629(10) 0.0474(19) Uani 0.67(5) 1 d D . P D 1
F3B F 0.764(3) 0.857(3) 0.224(2) 0.040(4) Uani 0.33(5) 1 d D . P D 2
F4B F 0.5770(13) 0.9473(14) 0.073(2) 0.042(3) Uani 0.33(5) 1 d D . P D 2
F5B F 0.659(3) 0.990(2) 0.244(2) 0.039(3) Uani 0.33(5) 1 d D . P D 2
F6B F 0.675(3) 0.815(3) 0.0525(17) 0.042(3) Uani 0.33(5) 1 d D . P D 2
N1 N 0.49316(17) 0.43847(17) 0.14921(15) 0.0291(4) Uani 1 1 d . . . . .
N2 N 0.52472(18) 0.26679(18) 0.20365(16) 0.0332(5) Uani 1 1 d . . . . .
N3 N 0.12871(18) 0.13684(17) 0.24535(14) 0.0266(4) Uani 1 1 d D . . . .
H3N H 0.066(2) 0.0599(17) 0.2233(18) 0.035(7) Uiso 1 1 d D . . . .
N4 N 0.23895(19) 0.06341(17) 0.14235(16) 0.0297(4) Uani 1 1 d D . . . .
H4N H 0.285(2) 0.082(2) 0.0967(16) 0.036(7) Uiso 1 1 d D . . . .
C1 C 0.4420(2) 0.3271(2) 0.18280(17) 0.0270(5) Uani 1 1 d . . . . .
C2 C 0.3137(2) 0.2856(2) 0.19787(17) 0.0271(5) Uani 1 1 d . . . . .
H2 H 0.280498 0.348438 0.210584 0.033 Uiso 1 1 calc R U . . .
C3 C 0.2272(2) 0.1603(2) 0.19639(17) 0.0244(5) Uani 1 1 d . . . . .
C4 C 0.4060(2) 0.4947(2) 0.1014(2) 0.0343(6) Uani 1 1 d . . . . .
H4A H 0.325656 0.428931 0.056074 0.052 Uiso 1 1 calc R U . . .
H4B H 0.451862 0.554622 0.060687 0.052 Uiso 1 1 calc R U . . .
H4C H 0.381608 0.538597 0.155110 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6298(2) 0.5280(2) 0.1965(2) 0.0398(6) Uani 1 1 d . . . . .
H5A H 0.628442 0.603398 0.234554 0.060 Uiso 1 1 calc R U . . .
H5B H 0.677721 0.550964 0.142401 0.060 Uiso 1 1 calc R U . . .
H5C H 0.674543 0.489280 0.244135 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6205(2) 0.2675(2) 0.1425(2) 0.0414(6) Uani 1 1 d . . . . .
H6A H 0.606295 0.307744 0.082910 0.062 Uiso 1 1 calc R U . . .
H6B H 0.608446 0.180986 0.118325 0.062 Uiso 1 1 calc R U . . .
H6C H 0.710818 0.314225 0.185244 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5191(3) 0.1906(3) 0.2837(2) 0.0461(7) Uani 1 1 d . . . . .
H7A H 0.463286 0.205748 0.327364 0.069 Uiso 1 1 calc R U . . .
H7B H 0.608870 0.212884 0.325998 0.069 Uiso 1 1 calc R U . . .
H7C H 0.481194 0.101624 0.251704 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1115(2) 0.21415(19) 0.33191(16) 0.0245(5) Uani 1 1 d . . . . .
C9 C 0.2427(2) 0.2941(2) 0.40979(18) 0.0364(6) Uani 1 1 d . . . . .
H9A H 0.302425 0.354962 0.375903 0.044 Uiso 1 1 calc R U . . .
H9B H 0.287021 0.239748 0.436378 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2140(3) 0.3647(3) 0.4998(2) 0.0496(7) Uani 1 1 d . . . . .
H10 H 0.299718 0.419078 0.550073 0.060 Uiso 1 1 calc R U . . .
C11 C 0.1259(3) 0.2696(3) 0.5547(2) 0.0498(7) Uani 1 1 d . . . . .
H11A H 0.171241 0.216308 0.581872 0.060 Uiso 1 1 calc R U . . .
H11B H 0.108805 0.314384 0.613389 0.060 Uiso 1 1 calc R U . . .
C12 C -0.0047(3) 0.1883(2) 0.47758(19) 0.0364(6) Uani 1 1 d . . . . .
H12 H -0.062481 0.125443 0.512443 0.044 Uiso 1 1 calc R U . . .
C13 C 0.0231(2) 0.1195(2) 0.38731(18) 0.0303(5) Uani 1 1 d . . . . .
H13A H -0.061742 0.065115 0.337825 0.036 Uiso 1 1 calc R U . . .
H13B H 0.068057 0.065380 0.413385 0.036 Uiso 1 1 calc R U . . .
C14 C 0.1435(3) 0.4463(3) 0.4585(2) 0.0565(8) Uani 1 1 d . . . . .
H14A H 0.126781 0.492721 0.516498 0.068 Uiso 1 1 calc R U . . .
H14B H 0.200459 0.508356 0.423752 0.068 Uiso 1 1 calc R U . . .
C15 C 0.0126(3) 0.3650(2) 0.3824(2) 0.0450(7) Uani 1 1 d . . . . .
H15 H -0.033320 0.419233 0.356013 0.054 Uiso 1 1 calc R U . . .
C16 C -0.0758(3) 0.2693(3) 0.4364(2) 0.0430(6) Uani 1 1 d . . . . .
H16A H -0.095259 0.313651 0.494028 0.052 Uiso 1 1 calc R U . . .
H16B H -0.161046 0.215824 0.386885 0.052 Uiso 1 1 calc R U . . .
C17 C 0.0399(2) 0.2959(2) 0.29209(19) 0.0335(5) Uani 1 1 d . . . . .
H17A H -0.044939 0.242785 0.242007 0.040 Uiso 1 1 calc R U . . .
H17B H 0.095357 0.357561 0.256179 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1720(2) -0.07415(19) 0.13691(17) 0.0256(5) Uani 1 1 d . . . . .
C19 C 0.1773(2) -0.1119(2) 0.24318(18) 0.0313(5) Uani 1 1 d . U . . .
H19A H 0.128779 -0.074731 0.281400 0.038 Uiso 1 1 calc R U . . .
H19B H 0.270774 -0.079902 0.283311 0.038 Uiso 1 1 calc R U . . .
C20 C 0.1143(2) -0.2556(2) 0.2305(2) 0.0337(5) Uani 1 1 d . U . . .
H20 H 0.127608 -0.275124 0.301867 0.040 Uiso 1 1 calc R U . E 1
C21 C 0.1884(2) -0.3149(2) 0.17376(18) 0.0328(5) Uani 1 1 d . . . . .
H21A H 0.155547 -0.406321 0.173608 0.039 Uiso 1 1 calc R U . F 1
H21B H 0.284890 -0.276163 0.205973 0.039 Uiso 1 1 calc R U . F 1
C22A C 0.1584(6) -0.2879(6) 0.0614(6) 0.0259(14) Uani 0.5 1 d D U P G 1
H22A H 0.198023 -0.330120 0.016714 0.031 Uiso 0.5 1 calc R U P G 1
C23A C 0.2253(7) -0.1452(7) 0.0692(6) 0.0296(16) Uani 0.5 1 d D U P G 1
H23A H 0.322043 -0.117403 0.097510 0.036 Uiso 0.5 1 calc R U P G 1
H23B H 0.211537 -0.124564 -0.000924 0.036 Uiso 0.5 1 calc R U P G 1
C24A C -0.0250(7) -0.2961(7) 0.1922(5) 0.0296(14) Uani 0.5 1 d D U P G 1
H24A H -0.060528 -0.251056 0.237248 0.035 Uiso 0.5 1 calc R U P G 1
H24B H -0.069622 -0.387222 0.191198 0.035 Uiso 0.5 1 calc R U P G 1
C25A C -0.0509(5) -0.2680(5) 0.0821(5) 0.0277(12) Uani 0.5 1 d D U P G 1
H25 H -0.148814 -0.299064 0.052518 0.033 Uiso 0.5 1 calc R U P G 1
C26A C 0.0087(6) -0.3334(5) 0.0142(4) 0.0324(11) Uani 0.5 1 d D U P G 1
H26A H -0.006451 -0.313973 -0.056314 0.039 Uiso 0.5 1 calc R U P G 1
H26B H -0.034558 -0.425470 0.009173 0.039 Uiso 0.5 1 calc R U P G 1
C27A C 0.0135(8) -0.1258(7) 0.0850(7) 0.0276(17) Uani 0.5 1 d D U P G 1
H27A H -0.027722 -0.082548 0.125931 0.033 Uiso 0.5 1 calc R U P G 1
H27B H -0.001001 -0.107850 0.014040 0.033 Uiso 0.5 1 calc R U P G 1
C22B C 0.2148(6) -0.2648(7) 0.0765(6) 0.0305(15) Uani 0.5 1 d D U P G 2
H22B H 0.275477 -0.297203 0.048557 0.037 Uiso 0.5 1 calc R U P G 2
C23B C 0.2732(7) -0.1212(7) 0.0952(6) 0.0277(15) Uani 0.5 1 d D U P G 2
H23C H 0.287481 -0.091129 0.030005 0.033 Uiso 0.5 1 calc R U P G 2
H23D H 0.359802 -0.087632 0.146458 0.033 Uiso 0.5 1 calc R U P G 2
C24B C -0.0313(7) -0.3084(7) 0.1470(6) 0.0355(16) Uani 0.5 1 d D U P G 2
H24C H -0.071979 -0.401273 0.136369 0.043 Uiso 0.5 1 calc R U P G 2
H24D H -0.091187 -0.275911 0.174570 0.043 Uiso 0.5 1 calc R U P G 2
C25B C -0.0145(6) -0.2664(6) 0.0441(5) 0.0354(13) Uani 0.5 1 d D U P G 2
H25B H -0.103018 -0.299269 -0.006232 0.039 Uiso 0.5 1 calc R U P G 2
C26B C 0.0793(7) -0.3136(5) -0.0001(5) 0.0358(12) Uani 0.5 1 d D U P G 2
H26C H 0.041134 -0.406513 -0.014064 0.043 Uiso 0.5 1 calc R U P G 2
H26D H 0.089784 -0.284205 -0.066094 0.043 Uiso 0.5 1 calc R U P G 2
C27B C 0.0456(8) -0.1213(7) 0.0625(7) 0.0306(17) Uani 0.5 1 d D U P G 2
H27C H 0.057676 -0.092109 -0.003363 0.037 Uiso 0.5 1 calc R U P G 2
H27D H -0.015456 -0.089073 0.088492 0.037 Uiso 0.5 1 calc R U P G 2
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'
Cl Cl 0.1484 0.1585 '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
Cl2A C28A Cl1A 118.0(10) . . ?
Cl2A C28A H28A 107.8 . . ?
Cl1A C28A H28A 107.8 . . ?
Cl2A C28A H28B 107.8 . . ?
Cl1A C28A H28B 107.8 . . ?
H28A C28A H28B 107.1 . . ?
Cl2B C28B Cl1B 106.6(9) . . ?
Cl2B C28B H28C 110.4 . . ?
Cl1B C28B H28C 110.4 . . ?
Cl2B C28B H28D 110.4 . . ?
Cl1B C28B H28D 110.4 . . ?
H28C C28B H28D 108.6 . . ?
Cl2C C28C Cl1C 115.0(18) . . ?
Cl2C C28C H28E 108.5 . . ?
Cl1C C28C H28E 108.5 . . ?
Cl2C C28C H28F 108.5 . . ?
Cl1C C28C H28F 108.5 . . ?
H28E C28C H28F 107.5 . . ?
F6B P1 F3B 95.5(12) . . ?
F5A P1 F4A 92.8(6) . . ?
F6B P1 F2 92.7(12) . . ?
F5A P1 F2 93.3(6) . . ?
F3B P1 F2 97.0(12) . . ?
F4A P1 F2 93.5(5) . . ?
F6B P1 F1 87.4(12) . . ?
F5A P1 F1 86.6(6) . . ?
F3B P1 F1 82.8(12) . . ?
F4A P1 F1 86.7(5) . . ?
F2 P1 F1 179.73(10) . . ?
F5A P1 F3A 91.7(5) . . ?
F4A P1 F3A 175.4(7) . . ?
F2 P1 F3A 87.2(7) . . ?
F1 P1 F3A 92.6(7) . . ?
F6B P1 F4B 92.0(8) . . ?
F3B P1 F4B 172.4(14) . . ?
F2 P1 F4B 83.3(6) . . ?
F1 P1 F4B 96.9(6) . . ?
F5A P1 F6A 178.3(8) . . ?
F4A P1 F6A 87.7(4) . . ?
F2 P1 F6A 88.3(5) . . ?
F1 P1 F6A 91.8(5) . . ?
F3A P1 F6A 87.8(6) . . ?
F6B P1 F5B 176.2(12) . . ?
F3B P1 F5B 88.2(11) . . ?
F2 P1 F5B 86.2(9) . . ?
F1 P1 F5B 93.6(9) . . ?
F4B P1 F5B 84.2(10) . . ?
C1 N1 C4 120.38(18) . . ?
C1 N1 C5 120.42(19) . . ?
C4 N1 C5 114.38(18) . . ?
C1 N2 C7 122.6(2) . . ?
C1 N2 C6 122.2(2) . . ?
C7 N2 C6 115.0(2) . . ?
C3 N3 C8 131.12(18) . . ?
C3 N3 H3N 112.6(16) . . ?
C8 N3 H3N 116.1(16) . . ?
C3 N4 C18 131.10(18) . . ?
C3 N4 H4N 115.5(17) . . ?
C18 N4 H4N 112.8(17) . . ?
N2 C1 N1 116.16(19) . . ?
N2 C1 C2 124.4(2) . . ?
N1 C1 C2 119.4(2) . . ?
C1 C2 C3 127.4(2) . . ?
C1 C2 H2 116.3 . . ?
C3 C2 H2 116.3 . . ?
N3 C3 N4 118.91(19) . . ?
N3 C3 C2 120.44(19) . . ?
N4 C3 C2 120.59(19) . . ?
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 C17 111.25(18) . . ?
N3 C8 C9 112.65(17) . . ?
C17 C8 C9 110.69(19) . . ?
N3 C8 C13 105.40(16) . . ?
C17 C8 C13 108.52(18) . . ?
C9 C8 C13 108.07(18) . . ?
C8 C9 C10 108.9(2) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C14 C10 C11 109.5(2) . . ?
C14 C10 C9 109.8(2) . . ?
C11 C10 C9 109.6(2) . . ?
C14 C10 H10 109.3 . . ?
C11 C10 H10 109.3 . . ?
C9 C10 H10 109.3 . . ?
C12 C11 C10 108.8(2) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C16 C12 C11 110.3(2) . . ?
C16 C12 C13 109.1(2) . . ?
C11 C12 C13 109.4(2) . . ?
C16 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
C12 C13 C8 110.48(18) . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C8 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C10 110.0(2) . . ?
C15 C14 H14A 109.7 . . ?
C10 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C10 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C17 109.2(2) . . ?
C14 C15 C16 109.6(2) . . ?
C17 C15 C16 109.6(2) . . ?
C14 C15 H15 109.5 . . ?
C17 C15 H15 109.5 . . ?
C16 C15 H15 109.5 . . ?
C12 C16 C15 109.2(2) . . ?
C12 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C12 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C8 C17 C15 109.8(2) . . ?
C8 C17 H17A 109.7 . . ?
C15 C17 H17A 109.7 . . ?
C8 C17 H17B 109.7 . . ?
C15 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C27B C18 N4 109.2(4) . . ?
N4 C18 C23A 111.1(3) . . ?
C27B C18 C19 118.7(4) . . ?
N4 C18 C19 112.99(18) . . ?
C23A C18 C19 111.7(4) . . ?
C27B C18 C23B 110.7(4) . . ?
N4 C18 C23B 100.7(3) . . ?
C19 C18 C23B 102.8(3) . . ?
N4 C18 C27A 111.7(3) . . ?
C23A C18 C27A 105.6(4) . . ?
C19 C18 C27A 103.3(3) . . ?
C18 C19 C20 109.58(19) . . ?
C18 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
C18 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C24A C20 C21 118.7(3) . . ?
C24A C20 C19 108.2(4) . . ?
C21 C20 C19 110.81(19) . . ?
C21 C20 C24B 100.8(3) . . ?
C19 C20 C24B 108.7(3) . . ?
C24A C20 H20 106.1 . . ?
C21 C20 H20 106.1 . . ?
C19 C20 H20 106.1 . . ?
C22B C21 C20 113.9(3) . . ?
C20 C21 C22A 104.1(3) . . ?
C20 C21 H21A 110.9 . . ?
C22A C21 H21A 110.9 . . ?
C20 C21 H21B 110.9 . . ?
C22A C21 H21B 110.9 . . ?
H21A C21 H21B 108.9 . . ?
C23A C22A C26A 109.8(5) . . ?
C23A C22A C21 106.6(5) . . ?
C26A C22A C21 112.1(5) . . ?
C23A C22A H22A 109.5 . . ?
C26A C22A H22A 109.5 . . ?
C21 C22A H22A 109.5 . . ?
C18 C23A C22A 112.7(5) . . ?
C18 C23A H23A 109.0 . . ?
C22A C23A H23A 109.0 . . ?
C18 C23A H23B 109.0 . . ?
C22A C23A H23B 109.0 . . ?
H23A C23A H23B 107.8 . . ?
C20 C24A C25A 108.2(5) . . ?
C20 C24A H24A 110.1 . . ?
C25A C24A H24A 110.1 . . ?
C20 C24A H24B 110.1 . . ?
C25A C24A H24B 110.1 . . ?
H24A C24A H24B 108.4 . . ?
C26A C25A C27A 108.9(5) . . ?
C26A C25A C24A 109.9(5) . . ?
C27A C25A C24A 109.7(5) . . ?
C26A C25A H25 109.5 . . ?
C27A C25A H25 109.5 . . ?
C24A C25A H25 109.5 . . ?
C25A C26A C22A 109.2(5) . . ?
C25A C26A H26A 109.8 . . ?
C22A C26A H26A 109.8 . . ?
C25A C26A H26B 109.8 . . ?
C22A C26A H26B 109.8 . . ?
H26A C26A H26B 108.3 . . ?
C25A C27A C18 109.6(6) . . ?
C25A C27A H27A 109.8 . . ?
C18 C27A H27A 109.8 . . ?
C25A C27A H27B 109.8 . . ?
C18 C27A H27B 109.8 . . ?
H27A C27A H27B 108.2 . . ?
C21 C22B C26B 105.6(5) . . ?
C21 C22B C23B 111.8(5) . . ?
C26B C22B C23B 108.8(5) . . ?
C21 C22B H22B 110.2 . . ?
C26B C22B H22B 110.2 . . ?
C23B C22B H22B 110.2 . . ?
C22B C23B C18 108.4(5) . . ?
C22B C23B H23C 110.0 . . ?
C18 C23B H23C 110.0 . . ?
C22B C23B H23D 110.0 . . ?
C18 C23B H23D 110.0 . . ?
H23C C23B H23D 108.4 . . ?
C25B C24B C20 110.0(5) . . ?
C25B C24B H24C 109.7 . . ?
C20 C24B H24C 109.7 . . ?
C25B C24B H24D 109.7 . . ?
C20 C24B H24D 109.7 . . ?
H24C C24B H24D 108.2 . . ?
C24B C25B C26B 111.1(5) . . ?
C24B C25B C27B 108.5(6) . . ?
C26B C25B C27B 108.6(5) . . ?
C24B C25B H25B 109.5 . . ?
C26B C25B H25B 109.5 . . ?
C27B C25B H25B 109.5 . . ?
C22B C26B C25B 110.1(5) . . ?
C22B C26B H26C 109.6 . . ?
C25B C26B H26C 109.6 . . ?
C22B C26B H26D 109.6 . . ?
C25B C26B H26D 109.6 . . ?
H26C C26B H26D 108.2 . . ?
C18 C27B C25B 109.4(6) . . ?
C18 C27B H27C 109.8 . . ?
C25B C27B H27C 109.8 . . ?
C18 C27B H27D 109.8 . . ?
C25B C27B H27D 109.8 . . ?
H27C C27B H27D 108.2 . . ?
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
C28A Cl2A 1.735(12) . ?
C28A Cl1A 1.774(12) . ?
C28A H28A 0.9900 . ?
C28A H28B 0.9900 . ?
C28B Cl2B 1.752(11) . ?
C28B Cl1B 1.767(12) . ?
C28B H28C 0.9900 . ?
C28B H28D 0.9900 . ?
C28C Cl2C 1.741(17) . ?
C28C Cl1C 1.786(17) . ?
C28C H28E 0.9900 . ?
C28C H28F 0.9900 . ?
P1 F6B 1.48(2) . ?
P1 F5A 1.532(13) . ?
P1 F3B 1.57(2) . ?
P1 F4A 1.588(6) . ?
P1 F2 1.5945(14) . ?
P1 F1 1.6012(15) . ?
P1 F3A 1.603(10) . ?
P1 F4B 1.604(12) . ?
P1 F6A 1.655(12) . ?
P1 F5B 1.71(2) . ?
N1 C1 1.369(3) . ?
N1 C4 1.450(3) . ?
N1 C5 1.468(3) . ?
N2 C1 1.358(3) . ?
N2 C7 1.452(3) . ?
N2 C6 1.463(3) . ?
N3 C3 1.341(3) . ?
N3 C8 1.485(3) . ?
N3 H3N 0.888(16) . ?
N4 C3 1.344(3) . ?
N4 C18 1.485(3) . ?
N4 H4N 0.862(16) . ?
C1 C2 1.393(3) . ?
C2 C3 1.419(3) . ?
C2 H2 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 C17 1.526(3) . ?
C8 C9 1.528(3) . ?
C8 C13 1.539(3) . ?
C9 C10 1.544(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C14 1.523(4) . ?
C10 C11 1.536(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.523(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.521(3) . ?
C12 C13 1.531(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.530(3) . ?
C15 C16 1.533(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C27B 1.444(10) . ?
C18 C23A 1.512(9) . ?
C18 C19 1.527(3) . ?
C18 C23B 1.589(9) . ?
C18 C27A 1.628(9) . ?
C19 C20 1.535(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C24A 1.420(8) . ?
C20 C21 1.517(3) . ?
C20 C24B 1.649(8) . ?
C20 H20 1.0000 . ?
C21 C22B 1.513(8) . ?
C21 C22A 1.567(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22A C23A 1.534(8) . ?
C22A C26A 1.536(8) . ?
C22A H22A 1.0000 . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.539(7) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.524(7) . ?
C25A C27A 1.537(8) . ?
C25A H25 1.0000 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C22B C26B 1.527(7) . ?
C22B C23B 1.530(8) . ?
C22B H22B 1.0000 . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.528(8) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.532(8) . ?
C25B C27B 1.546(8) . ?
C25B H25B 1.0000 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
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 F1 0.888(16) 2.68(2) 3.291(2) 127.3(19) 1_445 yes
N3 H3N H27A^a 0.888(16) 1.83(2) 2.650(9) 153(2) . yes
N3 H3N H27D^b 0.888(16) 2.17(2) 2.913(9) 140(2) . yes
N4 H4N F4A^a 0.862(16) 2.50(3) 3.33(2) 162(2) 2_665 yes
N4 H4N F6A^a 0.862(16) 2.76(3) 3.484(15) 143(2) 2_665 yes
N4 H4N F6B^b 0.862(16) 2.46(3) 3.23(3) 149(2) 2_665 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
C7 N2 C1 N1 147.9(2) . . . . ?
C6 N2 C1 N1 -36.2(3) . . . . ?
C7 N2 C1 C2 -29.1(4) . . . . ?
C6 N2 C1 C2 146.8(2) . . . . ?
C4 N1 C1 N2 165.0(2) . . . . ?
C5 N1 C1 N2 -41.0(3) . . . . ?
C4 N1 C1 C2 -17.9(3) . . . . ?
C5 N1 C1 C2 136.1(2) . . . . ?
N2 C1 C2 C3 -27.1(4) . . . . ?
N1 C1 C2 C3 156.0(2) . . . . ?
C8 N3 C3 N4 160.3(2) . . . . ?
C8 N3 C3 C2 -22.5(3) . . . . ?
C18 N4 C3 N3 -10.1(4) . . . . ?
C18 N4 C3 C2 172.7(2) . . . . ?
C1 C2 C3 N3 156.9(2) . . . . ?
C1 C2 C3 N4 -25.9(4) . . . . ?
C3 N3 C8 C17 90.1(3) . . . . ?
C3 N3 C8 C9 -34.9(3) . . . . ?
C3 N3 C8 C13 -152.5(2) . . . . ?
N3 C8 C9 C10 -176.7(2) . . . . ?
C17 C8 C9 C10 58.1(3) . . . . ?
C13 C8 C9 C10 -60.6(3) . . . . ?
C8 C9 C10 C14 -58.5(3) . . . . ?
C8 C9 C10 C11 61.8(3) . . . . ?
C14 C10 C11 C12 59.7(3) . . . . ?
C9 C10 C11 C12 -60.8(3) . . . . ?
C10 C11 C12 C16 -60.3(3) . . . . ?
C10 C11 C12 C13 59.7(3) . . . . ?
C16 C12 C13 C8 60.2(3) . . . . ?
C11 C12 C13 C8 -60.5(3) . . . . ?
N3 C8 C13 C12 -178.72(18) . . . . ?
C17 C8 C13 C12 -59.5(2) . . . . ?
C9 C8 C13 C12 60.6(2) . . . . ?
C11 C10 C14 C15 -59.9(3) . . . . ?
C9 C10 C14 C15 60.4(3) . . . . ?
C10 C14 C15 C17 -60.5(3) . . . . ?
C10 C14 C15 C16 59.5(3) . . . . ?
C11 C12 C16 C15 60.0(3) . . . . ?
C13 C12 C16 C15 -60.1(3) . . . . ?
C14 C15 C16 C12 -59.1(3) . . . . ?
C17 C15 C16 C12 60.6(3) . . . . ?
N3 C8 C17 C15 174.84(19) . . . . ?
C9 C8 C17 C15 -59.1(2) . . . . ?
C13 C8 C17 C15 59.3(2) . . . . ?
C14 C15 C17 C8 59.5(3) . . . . ?
C16 C15 C17 C8 -60.6(3) . . . . ?
C3 N4 C18 C27B 84.3(4) . . . . ?
C3 N4 C18 C23A -176.6(4) . . . . ?
C3 N4 C18 C19 -50.1(3) . . . . ?
C3 N4 C18 C23B -159.2(4) . . . . ?
C3 N4 C18 C27A 65.8(4) . . . . ?
C27B C18 C19 C20 53.9(4) . . . . ?
N4 C18 C19 C20 -176.33(18) . . . . ?
C23A C18 C19 C20 -50.2(3) . . . . ?
C23B C18 C19 C20 -68.6(3) . . . . ?
C27A C18 C19 C20 62.8(4) . . . . ?
C18 C19 C20 C24A -71.3(3) . . . . ?
C18 C19 C20 C21 60.4(3) . . . . ?
C18 C19 C20 C24B -49.6(4) . . . . ?
C19 C20 C21 C22B -48.1(4) . . . . ?
C24B C20 C21 C22B 66.9(4) . . . . ?
C24A C20 C21 C22A 58.0(5) . . . . ?
C19 C20 C21 C22A -68.1(3) . . . . ?
C20 C21 C22A C23A 66.2(5) . . . . ?
C20 C21 C22A C26A -53.9(5) . . . . ?
N4 C18 C23A C22A -179.9(4) . . . . ?
C19 C18 C23A C22A 52.9(6) . . . . ?
C27A C18 C23A C22A -58.6(6) . . . . ?
C26A C22A C23A C18 60.6(7) . . . . ?
C21 C22A C23A C18 -60.9(6) . . . . ?
C21 C20 C24A C25A -60.8(6) . . . . ?
C19 C20 C24A C25A 66.5(5) . . . . ?
C20 C24A C25A C26A 57.5(6) . . . . ?
C20 C24A C25A C27A -62.2(6) . . . . ?
C27A C25A C26A C22A 61.8(6) . . . . ?
C24A C25A C26A C22A -58.4(6) . . . . ?
C23A C22A C26A C25A -59.4(7) . . . . ?
C21 C22A C26A C25A 58.8(6) . . . . ?
C26A C25A C27A C18 -62.4(6) . . . . ?
C24A C25A C27A C18 57.9(7) . . . . ?
N4 C18 C27A C25A -179.6(4) . . . . ?
C23A C18 C27A C25A 59.5(6) . . . . ?
C19 C18 C27A C25A -57.9(5) . . . . ?
C20 C21 C22B C26B -69.7(5) . . . . ?
C20 C21 C22B C23B 48.4(6) . . . . ?
C21 C22B C23B C18 -58.4(6) . . . . ?
C26B C22B C23B C18 57.8(7) . . . . ?
C27B C18 C23B C22B -60.3(6) . . . . ?
N4 C18 C23B C22B -175.7(4) . . . . ?
C19 C18 C23B C22B 67.5(5) . . . . ?
C21 C20 C24B C25B -59.0(5) . . . . ?
C19 C20 C24B C25B 57.5(6) . . . . ?
C20 C24B C25B C26B 58.5(7) . . . . ?
C20 C24B C25B C27B -60.8(7) . . . . ?
C21 C22B C26B C25B 59.6(6) . . . . ?
C23B C22B C26B C25B -60.5(7) . . . . ?
C24B C25B C26B C22B -58.5(6) . . . . ?
C27B C25B C26B C22B 60.8(7) . . . . ?
N4 C18 C27B C25B 171.3(4) . . . . ?
C19 C18 C27B C25B -57.2(6) . . . . ?
C23B C18 C27B C25B 61.3(7) . . . . ?
C24B C25B C27B C18 59.2(7) . . . . ?
C26B C25B C27B C18 -61.7(7) . . . . ?
