#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:48:05 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272694 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/92/7709273.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_7709273
loop_
_publ_author_name
'Zhao, Minggang'
'Xue, Tingting'
'He, Ru-Ru'
'Ma, Jianping'
'Zheng, Wenjun'
_publ_section_title
;
 Ion-bearing stairs: alkali metal complexes of 1,2-diaza-4-phospholides.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1634
_journal_page_last               1645
_journal_paper_doi               10.1039/d1dt03601g
_journal_volume                  51
_journal_year                    2022
_chemical_formula_moiety         'C20 H36 K2 N4 O P2'
_chemical_formula_sum            'C20 H36 K2 N4 O P2'
_chemical_formula_weight         488.67
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-24 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                112.772(6)
_cell_angle_beta                 107.548(6)
_cell_angle_gamma                98.919(5)
_cell_formula_units_Z            2
_cell_length_a                   10.3502(6)
_cell_length_b                   12.2677(7)
_cell_length_c                   12.9852(10)
_cell_measurement_reflns_used    3308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9460
_cell_measurement_theta_min      3.0150
_cell_volume                     1378.53(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0251
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   42.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827  -77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   83.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   88.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827  178.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega   -1.00   83.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827   57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -52.00   32.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827  -57.0000 -150.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   22.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -      -17.0890  -99.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   32.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -       15.6827   57.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  8 omega  -46.00   54.00   1.0000   11.4150
omega____ theta____ kappa____ phi______ frames
    -      -17.0890   19.0000  150.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0341210000
_diffrn_orient_matrix_UB_12      0.0649895000
_diffrn_orient_matrix_UB_13      0.0356854000
_diffrn_orient_matrix_UB_21      -0.0098127000
_diffrn_orient_matrix_UB_22      0.0061972000
_diffrn_orient_matrix_UB_23      -0.0537026000
_diffrn_orient_matrix_UB_31      -0.0667165000
_diffrn_orient_matrix_UB_32      0.0092406000
_diffrn_orient_matrix_UB_33      -0.0028663000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16722
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.340
_diffrn_reflns_theta_min         3.022
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.177
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5628
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0524
_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)+(0.0716P)²+0.1183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3643
_reflns_number_total             5628
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1dt03601g2.cif
_cod_data_source_block           150114-1a
_cod_depositor_comments
'Adding full bibliography for 7709271--7709278.cif.'
_cod_original_cell_volume        1378.53(17)
_cod_database_code               7709273
_shelxl_version_number           2014-1
_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_max   0.954
_shelx_estimated_absorpt_t_min   0.898
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C6 \\sim C7 \\sim C8: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C14(H14), C3(H3), C11(H11), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b)
3.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C7(H7a,H7b,H7c), C15(H15a,H15b,H15c), C10(H10a,H10b,H10c),
 C1(H1a,H1b,H1c), C16(H16a,H16b,H16c), C9(H9a,H9b,H9c), C2(H2a,H2b,H2c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
K1 K 0.17709(7) 0.64404(6) 1.05933(6) 0.0632(2) Uani 1 1 d . . . . .
P1 P 0.03236(10) 0.81842(8) 1.26404(8) 0.0695(3) Uani 1 1 d . . . . .
P2 P 0.40790(9) 0.88894(7) 1.06386(7) 0.0601(2) Uani 1 1 d . . . . .
C8 C -0.1649(7) 0.9069(5) 1.0857(5) 0.1398(19) Uani 1 1 d . U . . .
H8A H -0.0720 0.9672 1.1341 0.210 Uiso 1 1 calc GR . . . .
H8B H -0.2144 0.9056 1.1372 0.210 Uiso 1 1 calc GR . . . .
H8C H -0.2176 0.9286 1.0259 0.210 Uiso 1 1 calc GR . . . .
N3 N 0.4832(2) 0.7195(2) 1.1205(2) 0.0510(6) Uani 1 1 d . . . . .
N4 N 0.4306(2) 0.6652(2) 0.9952(2) 0.0501(6) Uani 1 1 d . . . . .
C7 C -0.0795(7) 0.7802(6) 0.9425(5) 0.162(2) Uani 1 1 d . U . . .
H7A H -0.1351 0.7976 0.8803 0.243 Uiso 1 1 calc GR . . . .
H7B H -0.0698 0.6990 0.9056 0.243 Uiso 1 1 calc GR . . . .
H7C H 0.0131 0.8411 0.9873 0.243 Uiso 1 1 calc GR . . . .
C15 C 0.4584(4) 0.7162(4) 0.7795(3) 0.1021(14) Uani 1 1 d . . . . .
H15A H 0.5148 0.8022 0.8233 0.153 Uiso 1 1 calc GR . . . .
H15B H 0.4229 0.6907 0.6937 0.153 Uiso 1 1 calc GR . . . .
H15C H 0.5162 0.6667 0.7979 0.153 Uiso 1 1 calc GR . . . .
C13 C 0.3882(3) 0.7419(2) 0.9525(2) 0.0493(7) Uani 1 1 d . . . . .
C10 C 0.6998(4) 0.9722(4) 1.3553(3) 0.1010(13) Uani 1 1 d . . . . .
H10A H 0.7458 0.9102 1.3306 0.152 Uiso 1 1 calc GR . . . .
H10B H 0.7374 1.0162 1.4425 0.152 Uiso 1 1 calc GR . . . .
H10C H 0.7170 1.0295 1.3238 0.152 Uiso 1 1 calc GR . . . .
C4 C 0.0371(3) 0.6756(3) 1.2593(3) 0.0590(8) Uani 1 1 d . . . . .
C12 C 0.4795(3) 0.8354(3) 1.1690(3) 0.0518(7) Uani 1 1 d . . . . .
C14 C 0.3336(3) 0.6987(3) 0.8170(3) 0.0639(8) Uani 1 1 d . . . . .
H14 H 0.2809 0.6098 0.7752 0.077 Uiso 1 1 calc R . . . .
C1 C 0.0487(5) 0.5513(4) 1.3756(4) 0.1092(15) Uani 1 1 d . . . . .
H1A H -0.0338 0.5677 1.3895 0.164 Uiso 1 1 calc GR . . . .
H1B H 0.1101 0.5436 1.4427 0.164 Uiso 1 1 calc GR . . . .
H1C H 0.0196 0.4754 1.3020 0.164 Uiso 1 1 calc GR . . . .
C3 C 0.1267(4) 0.6557(4) 1.3638(3) 0.0787(10) Uani 1 1 d . . . . .
H3 H 0.1502 0.7315 1.4390 0.094 Uiso 1 1 calc R . . . .
C16 C 0.2327(4) 0.7672(4) 0.7779(3) 0.0965(13) Uani 1 1 d . . . . .
H16A H 0.2838 0.8541 0.8148 0.145 Uiso 1 1 calc GR . . . .
H16B H 0.1557 0.7567 0.8033 0.145 Uiso 1 1 calc GR . . . .
H16C H 0.1954 0.7338 0.6909 0.145 Uiso 1 1 calc GR . . . .
C11 C 0.5403(4) 0.9097(3) 1.3061(3) 0.0701(9) Uani 1 1 d . . . . .
H11 H 0.5253 0.8521 1.3397 0.084 Uiso 1 1 calc R . . . .
C9 C 0.4665(5) 1.0077(4) 1.3489(4) 0.1054(14) Uani 1 1 d . . . . .
H9A H 0.5082 1.0527 1.4362 0.158 Uiso 1 1 calc GR . . . .
H9B H 0.3668 0.9672 1.3217 0.158 Uiso 1 1 calc GR . . . .
H9C H 0.4784 1.0643 1.3157 0.158 Uiso 1 1 calc GR . . . .
C6 C -0.1506(4) 0.7843(4) 1.0249(3) 0.0768(10) Uani 1 1 d . U . . .
H6 H -0.2477 0.7274 0.9735 0.092 Uiso 1 1 calc R . . . .
C5 C -0.0831(3) 0.7334(3) 1.1098(3) 0.0545(7) Uani 1 1 d . . . . .
C2 C 0.2657(4) 0.6422(5) 1.3558(5) 0.1274(19) Uani 1 1 d . . . . .
H2A H 0.2475 0.5705 1.2815 0.191 Uiso 1 1 calc GR . . . .
H2B H 0.3212 0.6325 1.4238 0.191 Uiso 1 1 calc GR . . . .
H2C H 0.3173 0.7150 1.3569 0.191 Uiso 1 1 calc GR . . . .
N2 N -0.1119(2) 0.6110(2) 1.0654(2) 0.0548(6) Uani 1 1 d . . . . .
N1 N -0.0423(2) 0.5767(2) 1.1515(2) 0.0560(6) Uani 1 1 d . . . . .
K2 K 0.67471(6) 0.59757(6) 1.16621(6) 0.0555(2) Uani 1 1 d . . . . .
O1 O 0.7410(4) 0.6771(3) 1.4104(2) 0.1142(10) Uani 1 1 d . . . . .
C20 C 0.6512(6) 0.6285(6) 1.4485(5) 0.171(3) Uani 1 1 d . . . . .
H20A H 0.6490 0.5432 1.4284 0.206 Uiso 1 1 calc R . . . .
H20B H 0.5558 0.6281 1.4069 0.206 Uiso 1 1 calc R . . . .
C17 C 0.8491(7) 0.7818(6) 1.5134(5) 0.165(3) Uani 1 1 d . . . . .
H17A H 0.9422 0.7726 1.5197 0.198 Uiso 1 1 calc R . . . .
H17B H 0.8447 0.8568 1.5056 0.198 Uiso 1 1 calc R . . . .
C18 C 0.8279(7) 0.7904(6) 1.6175(5) 0.156(2) Uani 1 1 d . . . . .
H18A H 0.8248 0.8729 1.6644 0.187 Uiso 1 1 calc R . . . .
H18B H 0.9050 0.7745 1.6684 0.187 Uiso 1 1 calc R . . . .
C19 C 0.6945(8) 0.6987(7) 1.5768(6) 0.167(3) Uani 1 1 d . . . . .
H19A H 0.7066 0.6456 1.6159 0.201 Uiso 1 1 calc R . . . .
H19B H 0.6244 0.7382 1.5949 0.201 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'
K K 0.2009 0.2494 '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'
O O 0.0106 0.0060 '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
P2 K1 P1 99.69(3) . . ?
N3 K1 P1 120.25(5) . . ?
N3 K1 P2 46.84(5) . . ?
N3 K1 N4 26.98(6) . . ?
N3 K1 C13 42.51(7) . . ?
N3 K1 C4 124.02(7) . . ?
N3 K1 C12 25.04(7) . . ?
N3 K1 C5 145.23(8) . . ?
N3 K1 N2 165.09(7) . . ?
N3 K1 N1 143.17(7) . . ?
N4 K1 P1 142.09(5) . . ?
N4 K1 P2 46.59(5) . . ?
N4 K1 C13 24.31(6) . . ?
N4 K1 C4 150.89(7) . . ?
N4 K1 C12 43.04(7) . . ?
N4 K1 C5 153.38(7) . . ?
N4 K1 N1 163.72(7) . . ?
C13 K1 P1 129.02(6) . . ?
C13 K1 P2 29.81(5) . . ?
C13 K1 C4 153.98(8) . . ?
C4 K1 P1 28.89(6) . . ?
C4 K1 P2 124.54(6) . . ?
C12 K1 P1 99.40(6) . . ?
C12 K1 P2 29.99(5) . . ?
C12 K1 C13 43.97(7) . . ?
C12 K1 C4 113.01(8) . . ?
C12 K1 C5 120.76(8) . . ?
C5 K1 P1 29.25(6) . . ?
C5 K1 P2 107.92(6) . . ?
C5 K1 C13 129.64(8) . . ?
C5 K1 C4 43.28(7) . . ?
N2 K1 P1 45.52(5) . . ?
N2 K1 P1 128.12(5) 2_567 . ?
N2 K1 P2 131.27(6) . . ?
N2 K1 P2 132.17(5) 2_567 . ?
N2 K1 N3 100.26(7) 2_567 . ?
N2 K1 N4 167.01(7) . . ?
N2 K1 N4 87.69(6) 2_567 . ?
N2 K1 C13 102.57(7) 2_567 . ?
N2 K1 C13 145.98(7) . . ?
N2 K1 C4 41.98(7) . . ?
N2 K1 C4 102.10(8) 2_567 . ?
N2 K1 C12 144.02(8) . . ?
N2 K1 C12 125.26(8) 2_567 . ?
N2 K1 C5 24.41(7) . . ?
N2 K1 C5 113.70(8) 2_567 . ?
N2 K1 N2 89.55(7) 2_567 . ?
N2 K1 N1 82.70(7) 2_567 . ?
N2 K1 N1 26.69(6) . . ?
N1 K1 P1 45.41(5) . . ?
N1 K1 P1 129.01(5) 2_567 . ?
N1 K1 P2 119.42(5) 2_567 . ?
N1 K1 P2 145.07(6) . . ?
N1 K1 N3 110.47(7) 2_567 . ?
N1 K1 N4 87.95(7) 2_567 . ?
N1 K1 C13 91.85(7) 2_567 . ?
N1 K1 C13 171.94(8) . . ?
N1 K1 C4 24.17(7) . . ?
N1 K1 C4 113.86(7) 2_567 . ?
N1 K1 C12 137.03(7) . . ?
N1 K1 C12 130.97(7) 2_567 . ?
N1 K1 C5 103.08(8) 2_567 . ?
N1 K1 C5 42.34(7) . . ?
N1 K1 N2 29.10(7) 2_567 2_567 ?
N1 K1 N2 83.50(7) 2_567 . ?
N1 K1 N1 89.97(7) 2_567 . ?
K1 P1 K2 103.78(3) . 1_455 ?
C4 P1 K1 65.14(10) . . ?
C4 P1 C5 86.25(15) . . ?
C4 P1 K2 65.67(10) . 1_455 ?
C5 P1 K1 63.35(9) . . ?
C5 P1 K2 59.02(9) . 1_455 ?
C13 P2 K1 66.42(9) . . ?
C13 P2 C12 85.58(14) . . ?
C12 P2 K1 63.00(9) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
N4 N3 K1 79.18(13) . . ?
N4 N3 K2 100.57(15) . . ?
C12 N3 K1 86.26(16) . . ?
C12 N3 N4 112.2(2) . . ?
C12 N3 K2 136.20(19) . . ?
K2 N3 K1 129.19(9) . . ?
K1 N4 K2 109.05(7) . . ?
N3 N4 K1 73.84(12) . . ?
N3 N4 K2 54.93(12) . . ?
N3 N4 K2 125.73(16) . 2_667 ?
C13 N4 K1 88.23(15) . . ?
C13 N4 N3 112.1(2) . . ?
C13 N4 K2 118.78(18) . 2_667 ?
C13 N4 K2 151.24(17) . . ?
K2 N4 K1 89.74(6) 2_667 . ?
K2 N4 K2 85.06(6) 2_667 . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
P2 C13 K1 83.77(10) . . ?
N4 C13 K1 67.46(14) . . ?
N4 C13 P2 115.0(2) . . ?
N4 C13 C14 118.9(2) . . ?
C14 C13 K1 118.25(17) . . ?
C14 C13 P2 126.1(2) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
K1 C4 K2 119.44(9) . 1_455 ?
P1 C4 K1 85.96(11) . . ?
P1 C4 K2 86.75(11) . 1_455 ?
C3 C4 K1 112.2(2) . . ?
C3 C4 P1 125.9(3) . . ?
C3 C4 K2 120.24(19) . 1_455 ?
N1 C4 K1 67.43(15) . . ?
N1 C4 P1 115.1(2) . . ?
N1 C4 C3 119.0(3) . . ?
N1 C4 K2 62.13(14) . 1_455 ?
P2 C12 K1 87.01(10) . . ?
N3 C12 K1 68.70(15) . . ?
N3 C12 P2 115.1(2) . . ?
N3 C12 C11 118.5(3) . . ?
C11 C12 K1 113.75(18) . . ?
C11 C12 P2 126.3(2) . . ?
C15 C14 H14 108.2 . . ?
C15 C14 C16 110.4(3) . . ?
C13 C14 C15 109.9(3) . . ?
C13 C14 H14 108.2 . . ?
C13 C14 C16 111.7(3) . . ?
C16 C14 H14 108.2 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
C4 C3 H3 106.7 . . ?
C1 C3 C4 113.3(3) . . ?
C1 C3 H3 106.7 . . ?
C1 C3 C2 111.9(4) . . ?
C2 C3 C4 111.2(3) . . ?
C2 C3 H3 106.7 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C11 H11 108.1 . . ?
C10 C11 C9 109.9(3) . . ?
C12 C11 C10 110.5(3) . . ?
C12 C11 H11 108.1 . . ?
C12 C11 C9 112.1(3) . . ?
C9 C11 H11 108.1 . . ?
C11 C9 H9A 109.5 . . ?
C11 C9 H9B 109.5 . . ?
C11 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C6 C7 111.7(4) . . ?
C8 C6 H6 106.1 . . ?
C8 C6 C5 114.5(3) . . ?
C7 C6 H6 106.1 . . ?
C7 C6 C5 111.6(3) . . ?
C5 C6 H6 106.1 . . ?
K1 C5 K2 127.81(10) . 1_455 ?
P1 C5 K1 87.39(11) . . ?
P1 C5 K2 93.10(11) . 1_455 ?
C6 C5 K1 111.39(19) . . ?
C6 C5 P1 127.4(3) . . ?
C6 C5 K2 109.20(19) . 1_455 ?
N2 C5 K1 68.19(15) . . ?
N2 C5 P1 114.4(2) . . ?
N2 C5 C6 118.2(3) . . ?
N2 C5 K2 64.36(14) . 1_455 ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
K1 N2 K1 90.45(7) 2_567 . ?
K1 N2 K2 93.81(7) 2_567 1_455 ?
C5 N2 K1 87.40(16) . . ?
C5 N2 K1 171.6(2) . 2_567 ?
C5 N2 N1 112.5(2) . . ?
C5 N2 K2 91.27(16) . 1_455 ?
N1 N2 K1 74.94(16) . 2_567 ?
N1 N2 K1 77.92(14) . . ?
N1 N2 K2 81.96(14) . 1_455 ?
K2 N2 K1 157.58(9) 1_455 . ?
K1 N1 K1 90.03(7) 2_567 . ?
K1 N1 K2 145.17(9) . 1_455 ?
K1 N1 K2 91.17(7) 2_567 1_455 ?
C4 N1 K1 171.4(2) . 2_567 ?
C4 N1 K1 88.40(16) . . ?
C4 N1 N2 111.8(3) . . ?
C4 N1 K2 94.95(17) . 1_455 ?
N2 N1 K1 75.39(14) . . ?
N2 N1 K1 75.95(16) . 2_567 ?
N2 N1 K2 71.18(13) . 1_455 ?
K1 K2 K2 75.77(2) 2_667 2_667 ?
P1 K2 K1 81.87(2) 1_655 2_667 ?
P1 K2 K2 132.56(3) 1_655 2_667 ?
N3 K2 K1 131.50(5) . 2_667 ?
N3 K2 P1 105.68(5) . 1_655 ?
N3 K2 N4 113.54(7) . 2_667 ?
N3 K2 N4 24.50(6) . . ?
N3 K2 C4 133.26(8) . 1_655 ?
N3 K2 C5 98.49(7) . 1_655 ?
N3 K2 N2 115.57(7) . 1_655 ?
N3 K2 N1 140.44(7) . 1_655 ?
N3 K2 K2 63.98(5) . 2_667 ?
N3 K2 O1 99.50(9) . . ?
N4 K2 K1 107.19(4) . 2_667 ?
N4 K2 K1 46.21(4) 2_667 2_667 ?
N4 K2 P1 127.63(5) 2_667 1_655 ?
N4 K2 P1 108.92(4) . 1_655 ?
N4 K2 N4 94.95(6) 2_667 . ?
N4 K2 C4 132.85(7) . 1_655 ?
N4 K2 C4 105.43(7) 2_667 1_655 ?
N4 K2 C5 110.58(7) 2_667 1_655 ?
N4 K2 N2 87.23(7) 2_667 1_655 ?
N4 K2 N1 84.77(7) 2_667 1_655 ?
N4 K2 K2 43.47(4) . 2_667 ?
N4 K2 K2 51.47(5) 2_667 2_667 ?
C4 K2 K1 64.48(6) 1_655 2_667 ?
C4 K2 P1 27.58(6) 1_655 1_655 ?
C4 K2 K2 135.87(6) 1_655 2_667 ?
C5 K2 K1 66.04(6) 1_655 2_667 ?
C5 K2 P1 27.88(5) 1_655 1_655 ?
C5 K2 N4 91.12(7) 1_655 . ?
C5 K2 C4 42.04(7) 1_655 1_655 ?
C5 K2 K2 104.95(6) 1_655 2_667 ?
N2 K2 K1 41.78(5) 1_655 2_667 ?
N2 K2 P1 43.83(5) 1_655 1_655 ?
N2 K2 N4 100.40(6) 1_655 . ?
N2 K2 C4 40.74(7) 1_655 1_655 ?
N2 K2 C5 24.38(7) 1_655 1_655 ?
N2 K2 N1 26.86(7) 1_655 1_655 ?
N2 K2 K2 96.23(5) 1_655 2_667 ?
N1 K2 K1 41.65(5) 1_655 2_667 ?
N1 K2 P1 43.58(5) 1_655 1_655 ?
N1 K2 N4 127.25(6) 1_655 . ?
N1 K2 C4 22.92(7) 1_655 1_655 ?
N1 K2 C5 42.17(7) 1_655 1_655 ?
N1 K2 K2 114.36(5) 1_655 2_667 ?
O1 K2 K1 128.99(7) . 2_667 ?
O1 K2 P1 85.78(8) . 1_655 ?
O1 K2 N4 118.77(9) . 2_667 ?
O1 K2 N4 123.60(8) . . ?
O1 K2 C4 82.64(9) . 1_655 ?
O1 K2 C5 113.63(10) . 1_655 ?
O1 K2 N2 123.24(9) . 1_655 ?
O1 K2 N1 101.29(9) . 1_655 ?
O1 K2 K2 140.09(8) . 2_667 ?
C20 O1 K2 120.7(3) . . ?
C20 O1 C17 107.9(4) . . ?
C17 O1 K2 130.4(3) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
O1 C20 C19 110.8(5) . . ?
H20A C20 H20B 108.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
O1 C17 H17A 110.0 . . ?
O1 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C18 C17 O1 108.5(5) . . ?
C18 C17 H17A 110.0 . . ?
C18 C17 H17B 110.0 . . ?
C17 C18 H18A 110.3 . . ?
C17 C18 H18B 110.3 . . ?
C17 C18 C19 107.1(5) . . ?
H18A C18 H18B 108.6 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
C20 C19 C18 105.2(5) . . ?
C20 C19 H19A 110.7 . . ?
C20 C19 H19B 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
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
K1 P1 3.5887(12) . ?
K1 P2 3.5057(11) . ?
K1 N3 2.920(2) . ?
K1 N4 2.986(2) . ?
K1 C13 3.232(3) . ?
K1 C4 3.264(3) . ?
K1 C12 3.128(3) . ?
K1 C5 3.211(3) . ?
K1 N2 2.984(2) . ?
K1 N2 2.762(3) 2_567 ?
K1 N1 3.016(2) . ?
K1 N1 2.750(3) 2_567 ?
P1 C4 1.738(3) . ?
P1 C5 1.755(3) . ?
P1 K2 3.7479(11) 1_455 ?
P2 C13 1.753(3) . ?
P2 C12 1.755(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C6 1.459(6) . ?
N3 N4 1.380(3) . ?
N3 C12 1.327(4) . ?
N3 K2 2.723(2) . ?
N4 C13 1.331(3) . ?
N4 K2 2.876(2) 2_667 ?
N4 K2 3.270(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C6 1.461(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C14 1.525(5) . ?
C13 C14 1.511(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 C11 1.521(5) . ?
C4 C3 1.527(4) . ?
C4 N1 1.337(4) . ?
C4 K2 3.421(3) 1_455 ?
C12 C11 1.512(4) . ?
C14 H14 0.9800 . ?
C14 C16 1.528(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C3 1.489(5) . ?
C3 H3 0.9800 . ?
C3 C2 1.503(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C9 1.536(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6 0.9800 . ?
C6 C5 1.515(4) . ?
C5 N2 1.328(4) . ?
C5 K2 3.218(3) 1_455 ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
N2 K1 2.762(3) 2_567 ?
N2 N1 1.385(3) . ?
N2 K2 2.902(2) 1_455 ?
N1 K1 2.750(3) 2_567 ?
N1 K2 3.035(2) 1_455 ?
K2 K1 4.1369(9) 2_667 ?
K2 P1 3.7480(11) 1_655 ?
K2 N4 2.876(2) 2_667 ?
K2 C4 3.421(3) 1_655 ?
K2 C5 3.218(3) 1_655 ?
K2 N2 2.902(2) 1_655 ?
K2 N1 3.035(2) 1_655 ?
K2 K2 4.1650(13) 2_667 ?
K2 O1 2.750(3) . ?
O1 C20 1.341(6) . ?
O1 C17 1.419(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C19 1.427(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.400(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.438(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
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
K1 P1 C4 C3 114.6(3) . . . . ?
K1 P1 C4 N1 -62.8(2) . . . . ?
K1 P1 C4 K2 -119.84(8) . . . 1_455 ?
K1 P1 C5 C6 -115.1(3) . . . . ?
K1 P1 C5 N2 64.59(19) . . . . ?
K1 P1 C5 K2 127.75(10) . . . 1_455 ?
K1 P2 C13 N4 -61.56(18) . . . . ?
K1 P2 C13 C14 120.6(3) . . . . ?
K1 P2 C12 N3 64.78(19) . . . . ?
K1 P2 C12 C11 -117.5(3) . . . . ?
K1 N3 N4 C13 81.22(19) . . . . ?
K1 N3 N4 K2 -128.22(9) . . . . ?
K1 N3 N4 K2 -77.63(14) . . . 2_667 ?
K1 N3 C12 P2 -75.86(17) . . . . ?
K1 N3 C12 C11 106.3(2) . . . . ?
K1 N4 C13 P2 71.16(16) . . . . ?
K1 N4 C13 C14 -110.9(2) . . . . ?
K1 C13 C14 C15 -160.6(2) . . . . ?
K1 C13 C14 C16 76.6(3) . . . . ?
K1 C4 C3 C1 -120.0(3) . . . . ?
K1 C4 C3 C2 7.0(4) . . . . ?
K1 C4 N1 N2 -73.57(18) . . . . ?
K1 C4 N1 K2 -145.27(10) . . . 1_455 ?
K1 C12 C11 C10 163.8(2) . . . . ?
K1 C12 C11 C9 -73.2(3) . . . . ?
K1 C5 N2 N1 75.79(18) . . . . ?
K1 C5 N2 K2 157.61(9) . . . 1_455 ?
K1 N2 N1 K1 -93.77(5) . . . 2_567 ?
K1 N2 N1 K1 93.77(5) 2_567 . . . ?
K1 N2 N1 C4 176.0(2) 2_567 . . . ?
K1 N2 N1 C4 82.2(2) . . . . ?
K1 N2 N1 K2 -96.17(5) 2_567 . . 1_455 ?
K1 N2 N1 K2 170.06(7) . . . 1_455 ?
P1 C4 C3 C1 138.4(3) . . . . ?
P1 C4 C3 C2 -94.6(4) . . . . ?
P1 C4 N1 K1 73.82(18) . . . . ?
P1 C4 N1 N2 0.3(3) . . . . ?
P1 C4 N1 K2 -71.44(19) . . . 1_455 ?
P1 C5 N2 K1 -76.37(16) . . . . ?
P1 C5 N2 N1 -0.6(3) . . . . ?
P1 C5 N2 K2 81.24(17) . . . 1_455 ?
P2 C13 C14 C15 95.6(3) . . . . ?
P2 C13 C14 C16 -27.3(4) . . . . ?
P2 C12 C11 C10 -91.5(4) . . . . ?
P2 C12 C11 C9 31.5(4) . . . . ?
C8 C6 C5 K1 -128.4(3) . . . . ?
C8 C6 C5 P1 -24.6(5) . . . . ?
C8 C6 C5 N2 155.7(4) . . . . ?
C8 C6 C5 K2 85.2(4) . . . 1_455 ?
N3 N4 C13 K1 -71.74(17) . . . . ?
N3 N4 C13 P2 -0.6(3) . . . . ?
N3 N4 C13 C14 177.4(2) . . . . ?
N3 C12 C11 C10 86.1(4) . . . . ?
N3 C12 C11 C9 -150.9(3) . . . . ?
N4 N3 C12 K1 76.71(17) . . . . ?
N4 N3 C12 P2 0.8(3) . . . . ?
N4 N3 C12 C11 -177.0(2) . . . . ?
N4 C13 C14 C15 -82.1(3) . . . . ?
N4 C13 C14 C16 155.0(3) . . . . ?
C7 C6 C5 K1 -0.3(4) . . . . ?
C7 C6 C5 P1 103.5(4) . . . . ?
C7 C6 C5 N2 -76.2(4) . . . . ?
C7 C6 C5 K2 -146.8(4) . . . 1_455 ?
C13 P2 C12 K1 -65.73(10) . . . . ?
C13 P2 C12 N3 -1.0(2) . . . . ?
C13 P2 C12 C11 176.7(3) . . . . ?
C4 P1 C5 K1 -64.00(11) . . . . ?
C4 P1 C5 C6 -179.1(3) . . . . ?
C4 P1 C5 N2 0.6(2) . . . . ?
C4 P1 C5 K2 63.75(11) . . . 1_455 ?
C12 P2 C13 K1 62.41(10) . . . . ?
C12 P2 C13 N4 0.9(2) . . . . ?
C12 P2 C13 C14 -176.9(3) . . . . ?
C12 N3 N4 K1 -81.38(19) . . . . ?
C12 N3 N4 C13 -0.2(3) . . . . ?
C12 N3 N4 K2 150.4(2) . . . . ?
C12 N3 N4 K2 -159.01(17) . . . 2_667 ?
C3 C4 N1 K1 -103.7(3) . . . . ?
C3 C4 N1 N2 -177.3(2) . . . . ?
C3 C4 N1 K2 111.0(2) . . . 1_455 ?
C6 C5 N2 K1 103.4(2) . . . . ?
C6 C5 N2 N1 179.2(2) . . . . ?
C6 C5 N2 K2 -99.0(2) . . . 1_455 ?
C5 P1 C4 K1 62.29(10) . . . . ?
C5 P1 C4 C3 176.9(3) . . . . ?
C5 P1 C4 N1 -0.5(2) . . . . ?
C5 P1 C4 K2 -57.55(10) . . . 1_455 ?
C5 N2 N1 K1 -175.8(2) . . . 2_567 ?
C5 N2 N1 K1 -82.02(19) . . . . ?
C5 N2 N1 C4 0.2(3) . . . . ?
C5 N2 N1 K2 88.0(2) . . . 1_455 ?
N1 C4 C3 C1 -44.3(5) . . . . ?
N1 C4 C3 C2 82.7(4) . . . . ?
K2 P1 C4 K1 119.84(8) 1_455 . . . ?
K2 P1 C4 C3 -125.5(3) 1_455 . . . ?
K2 P1 C4 N1 57.08(19) 1_455 . . . ?
K2 P1 C5 K1 -127.75(10) 1_455 . . . ?
K2 P1 C5 C6 117.1(3) 1_455 . . . ?
K2 P1 C5 N2 -63.16(18) 1_455 . . . ?
K2 N3 N4 K1 128.22(9) . . . . ?
K2 N3 N4 C13 -150.55(17) . . . . ?
K2 N3 N4 K2 50.60(17) . . . 2_667 ?
K2 N3 C12 K1 -147.9(2) . . . . ?
K2 N3 C12 P2 136.28(18) . . . . ?
K2 N3 C12 C11 -41.6(4) . . . . ?
K2 N4 C13 K1 88.73(12) 2_667 . . . ?
K2 N4 C13 K1 -128.5(4) . . . . ?
K2 N4 C13 P2 -57.3(4) . . . . ?
K2 N4 C13 P2 159.89(11) 2_667 . . . ?
K2 N4 C13 C14 120.6(3) . . . . ?
K2 N4 C13 C14 -22.1(3) 2_667 . . . ?
K2 C4 C3 C1 28.5(4) 1_455 . . . ?
K2 C4 C3 C2 155.5(3) 1_455 . . . ?
K2 C4 N1 K1 145.27(10) 1_455 . . . ?
K2 C4 N1 N2 71.70(18) 1_455 . . . ?
K2 C5 N2 K1 -157.61(9) 1_455 . . . ?
K2 C5 N2 N1 -81.82(18) 1_455 . . . ?
K2 N2 N1 K1 96.17(5) 1_455 . . 2_567 ?
K2 N2 N1 K1 -170.06(7) 1_455 . . . ?
K2 N2 N1 C4 -87.8(2) 1_455 . . . ?
K2 O1 C20 C19 -169.3(4) . . . . ?
K2 O1 C17 C18 172.7(4) . . . . ?
O1 C20 C19 C18 -4.8(9) . . . . ?
O1 C17 C18 C19 -7.1(8) . . . . ?
C20 O1 C17 C18 4.2(8) . . . . ?
C17 O1 C20 C19 0.5(8) . . . . ?
C17 C18 C19 C20 7.2(9) . . . . ?
