#------------------------------------------------------------------------------
#$Date: 2024-10-04 20:22:16 +0200 (Fri 04 de Oct de 2024) $
#$Revision: 295056 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/71/7717154.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_7717154
loop_
_publ_author_name
'Calder, Ethan D. E.'
'Male, Louise'
'Jupp, Andrew R.'
_publ_section_title
;
 Accessing five- and seven-membered phosphorus-based heterocycles
 via cycloaddition reactions of azophosphines.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15032
_journal_page_last               15039
_journal_paper_doi               10.1039/d4dt02248c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C25 H39 N2 O4 P'
_chemical_formula_sum            'C25 H39 N2 O4 P'
_chemical_formula_weight         462.55
_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     dual
_audit_creation_date             2024-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                94.526(3)
_cell_angle_beta                 97.708(3)
_cell_angle_gamma                103.731(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0234(3)
_cell_length_b                   8.2718(3)
_cell_length_c                   19.6948(7)
_cell_measurement_reflns_used    7075
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.7820
_cell_measurement_theta_min      4.5030
_cell_volume                     1249.92(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    5.87    --  -41.27 -38.00-150.00   99
  2  ω    -66.00  33.00   1.00    5.87    --  -41.27  38.00  30.00   99
  3  ω    -87.00  -6.00   1.00    5.87    --  -41.27 125.00  90.00   81
  4  ω    -21.00  74.00   1.00    5.87    --   41.27 -77.00  60.00   95
  5  ω      6.00  82.00   1.00    5.87    --   41.27 -99.00  90.00   76
  6  ω     61.00 146.00   1.00   23.49    --  103.11 178.00 120.00   85
  7  ω     61.00 146.00   1.00   23.49    --  103.11 178.00-180.00   85
  8  ω     30.00 129.00   1.00   23.49    --  103.11 -45.00-120.00   99
  9  ω     75.00 178.00   1.00   23.49    --  103.11  30.00-150.00  103
 10  ω     27.00 109.00   1.00   23.49    --  103.11-111.00 -90.00   82
 11  ω     27.00 109.00   1.00   23.49    --  103.11-111.00-180.00   82
 12  ω    103.00 178.00   1.00   23.49    --  103.11  77.00 -30.00   75
 13  ω     61.00 146.00   1.00   23.49    --  103.11 178.00  60.00   85
 14  ω     27.00 109.00   1.00   23.49    --  103.11-111.00 120.00   82
 15  ω     75.00 178.00   1.00   23.49    --  103.11  30.00 -60.00  103
 16  ω     30.00 129.00   1.00   23.49    --  103.11 -45.00   0.00   99
 17  ω     30.00 129.00   1.00   23.49    --  103.11 -45.00 120.00   99
 18  ω   -113.00 -13.00   1.00    5.87    --  -41.27 -57.00 120.00  100
 19  ω   -113.00 -25.00   1.00    5.87    --  -41.27 -57.00 -60.00   88
 20  ω   -113.00 -13.00   1.00    5.87    --  -41.27 -57.00  30.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196472000
_diffrn_orient_matrix_UB_12      0.0907074000
_diffrn_orient_matrix_UB_13      0.0731063000
_diffrn_orient_matrix_UB_21      -0.0064779000
_diffrn_orient_matrix_UB_22      0.1642819000
_diffrn_orient_matrix_UB_23      -0.0308304000
_diffrn_orient_matrix_UB_31      -0.1990949000
_diffrn_orient_matrix_UB_32      -0.0450959000
_diffrn_orient_matrix_UB_33      -0.0043932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.838
_diffrn_reflns_theta_min         4.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.234
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0416
_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)+(0.0425P)²+0.6227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4027
_reflns_number_total             4852
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_076_7b_gaussian
_cod_database_code               7717154
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C25 H39 O4 N2 P1'
_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   0.941
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C14(H14A,H14B)
1.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3)
1.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C24(H24A,H24B,
 H24C), C19(H19A,H19B,H19C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C23(H23A,H23B,
 H23C), C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.495
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
P1 P 0.71271(5) 0.22035(5) 0.83616(2) 0.01208(11) Uani 1 1 d . . . . .
O2 O 0.47981(15) 0.24653(15) 0.60603(6) 0.0166(3) Uani 1 1 d . . . . .
O4 O 0.38552(15) -0.09343(15) 0.80158(6) 0.0171(3) Uani 1 1 d . . . . .
O1 O 0.64579(17) 0.06185(16) 0.59846(7) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.35811(16) -0.08692(16) 0.68632(7) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.77124(18) 0.34347(17) 0.73002(7) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.82232(18) 0.37978(17) 0.80211(7) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.7627(2) 0.6010(2) 0.67973(9) 0.0161(3) Uani 1 1 d . . . . .
C1 C 0.8413(2) 0.4682(2) 0.68723(9) 0.0140(3) Uani 1 1 d . . . . .
C18 C 0.8614(2) 0.0966(2) 0.87396(9) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.5821(2) 0.1138(2) 0.75907(8) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.4343(2) -0.0282(2) 0.74372(9) 0.0152(3) Uani 1 1 d . . . . .
C12 C 0.5896(2) 0.1607(2) 0.63105(9) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.6451(2) 0.2072(2) 0.70748(9) 0.0137(3) Uani 1 1 d . . . . .
C5 C 1.0397(2) 0.5739(2) 0.61156(9) 0.0191(4) Uani 1 1 d . . . . .
H5 H 1.133087 0.564512 0.587794 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8287(2) 0.7208(2) 0.63775(9) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.778546 0.813096 0.632758 0.022 Uiso 1 1 calc R U . . .
C22 C 0.5961(2) 0.3019(2) 0.90166(9) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.9808(2) 0.4525(2) 0.65384(9) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.9657(2) 0.7090(2) 0.60301(9) 0.0189(4) Uani 1 1 d . . . . .
C17 C 0.2055(2) -0.2930(2) 0.85887(10) 0.0231(4) Uani 1 1 d . . . . .
H17A H 0.108383 -0.393129 0.852533 0.035 Uiso 1 1 calc R U . . .
H17B H 0.175443 -0.201385 0.885260 0.035 Uiso 1 1 calc R U . . .
H17C H 0.309058 -0.317318 0.883977 0.035 Uiso 1 1 calc R U . . .
C16 C 0.2419(2) -0.2422(2) 0.78932(10) 0.0183(4) Uani 1 1 d . . . . .
H16A H 0.272925 -0.333617 0.762198 0.022 Uiso 1 1 calc R U . . .
H16B H 0.137891 -0.218032 0.763284 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4307(2) 0.2231(2) 0.53096(9) 0.0193(4) Uani 1 1 d . . . . .
H14A H 0.327914 0.267473 0.518265 0.023 Uiso 1 1 calc R U . . .
H14B H 0.398815 0.102029 0.514377 0.023 Uiso 1 1 calc R U . . .
C20 C 0.9900(2) 0.2005(3) 0.93534(10) 0.0255(4) Uani 1 1 d . . . . .
H20A H 1.042438 0.311086 0.922438 0.038 Uiso 1 1 calc R U . . .
H20B H 1.081224 0.143263 0.948454 0.038 Uiso 1 1 calc R U . . .
H20C H 0.928597 0.213793 0.974400 0.038 Uiso 1 1 calc R U . . .
C21 C 0.7663(3) -0.0726(2) 0.89410(11) 0.0237(4) Uani 1 1 d . . . . .
H21A H 0.711949 -0.053588 0.934697 0.036 Uiso 1 1 calc R U . . .
H21B H 0.849652 -0.139989 0.904802 0.036 Uiso 1 1 calc R U . . .
H21C H 0.676638 -0.132109 0.855641 0.036 Uiso 1 1 calc R U . . .
C24 C 0.7171(3) 0.4627(2) 0.94195(10) 0.0258(4) Uani 1 1 d . . . . .
H24A H 0.812260 0.434591 0.971392 0.039 Uiso 1 1 calc R U . . .
H24B H 0.651390 0.517963 0.970691 0.039 Uiso 1 1 calc R U . . .
H24C H 0.764779 0.538255 0.909513 0.039 Uiso 1 1 calc R U . . .
C19 C 0.9624(2) 0.0630(2) 0.81579(10) 0.0227(4) Uani 1 1 d . . . . .
H19A H 0.881422 -0.003866 0.776227 0.034 Uiso 1 1 calc R U . . .
H19B H 1.047559 0.001507 0.832119 0.034 Uiso 1 1 calc R U . . .
H19C H 1.022745 0.169703 0.801857 0.034 Uiso 1 1 calc R U . . .
C7 C 1.0678(2) 0.3113(2) 0.66398(11) 0.0238(4) Uani 1 1 d . . . . .
H7A H 1.124264 0.322520 0.712019 0.036 Uiso 1 1 calc R U . . .
H7B H 1.155018 0.315927 0.633333 0.036 Uiso 1 1 calc R U . . .
H7C H 0.980466 0.203892 0.653187 0.036 Uiso 1 1 calc R U . . .
C8 C 0.6097(2) 0.6134(2) 0.71464(10) 0.0217(4) Uani 1 1 d . . . . .
H8A H 0.518163 0.509155 0.702416 0.032 Uiso 1 1 calc R U . . .
H8B H 0.565263 0.707368 0.699479 0.032 Uiso 1 1 calc R U . . .
H8C H 0.646184 0.631741 0.764746 0.032 Uiso 1 1 calc R U . . .
C23 C 0.4400(2) 0.3461(3) 0.86027(10) 0.0245(4) Uani 1 1 d . . . . .
H23A H 0.480917 0.425430 0.828058 0.037 Uiso 1 1 calc R U . . .
H23B H 0.377480 0.397054 0.891941 0.037 Uiso 1 1 calc R U . . .
H23C H 0.361804 0.244051 0.834415 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5782(3) 0.3120(3) 0.49650(10) 0.0250(4) Uani 1 1 d . . . . .
H15A H 0.537441 0.307501 0.447042 0.038 Uiso 1 1 calc R U . . .
H15B H 0.673735 0.256899 0.503221 0.038 Uiso 1 1 calc R U . . .
H15C H 0.619156 0.429124 0.516894 0.038 Uiso 1 1 calc R U . . .
C25 C 0.5304(3) 0.1767(2) 0.95124(9) 0.0222(4) Uani 1 1 d . . . . .
H25A H 0.459108 0.072253 0.924742 0.033 Uiso 1 1 calc R U . . .
H25B H 0.460393 0.223964 0.980675 0.033 Uiso 1 1 calc R U . . .
H25C H 0.629711 0.153736 0.980062 0.033 Uiso 1 1 calc R U . . .
C9 C 1.0353(2) 0.8413(3) 0.55845(10) 0.0248(4) Uani 1 1 d . . . . .
H9A H 1.153653 0.902500 0.579203 0.037 Uiso 1 1 calc R U . . .
H9B H 0.960711 0.919456 0.554817 0.037 Uiso 1 1 calc R U . . .
H9C H 1.036656 0.787970 0.512364 0.037 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 11 0.0197
0 -2 -11 0.0232
1 2 9 0.0374
1 -2 -11 0.0329
1 -5 4 0.0443
-5 0 1 0.0706
-2 5 -1 0.0441
-1 5 -2 0.0328
2 -5 1 0.0597
-1 3 -11 0.0393
0 -1 13 0.0295
2 0 10 0.0546
1 -5 -6 0.0312
1 4 4 0.0425
-1 3 9 0.0181
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
N2 P1 C18 110.41(8) . . ?
N2 P1 C11 97.08(8) . . ?
N2 P1 C22 108.63(8) . . ?
C11 P1 C18 111.51(8) . . ?
C11 P1 C22 115.99(8) . . ?
C22 P1 C18 112.14(8) . . ?
C12 O2 C14 115.60(13) . . ?
C13 O4 C16 115.19(13) . . ?
N2 N1 C1 117.93(13) . . ?
C10 N1 N2 117.00(14) . . ?
C10 N1 C1 124.43(15) . . ?
N1 N2 P1 106.22(10) . . ?
C1 C2 C8 121.36(16) . . ?
C3 C2 C1 117.85(16) . . ?
C3 C2 C8 120.78(16) . . ?
C2 C1 N1 117.68(15) . . ?
C2 C1 C6 122.13(16) . . ?
C6 C1 N1 120.17(15) . . ?
C20 C18 P1 110.66(13) . . ?
C20 C18 C21 110.84(15) . . ?
C20 C18 C19 108.71(15) . . ?
C21 C18 P1 113.77(12) . . ?
C19 C18 P1 104.17(12) . . ?
C19 C18 C21 108.36(15) . . ?
C13 C11 P1 133.78(13) . . ?
C10 C11 P1 104.36(12) . . ?
C10 C11 C13 121.73(15) . . ?
O4 C13 C11 112.53(14) . . ?
O3 C13 O4 122.12(15) . . ?
O3 C13 C11 125.35(16) . . ?
O2 C12 C10 111.06(14) . . ?
O1 C12 O2 126.47(16) . . ?
O1 C12 C10 122.42(16) . . ?
N1 C10 C11 114.95(15) . . ?
N1 C10 C12 118.97(15) . . ?
C11 C10 C12 125.98(15) . . ?
C6 C5 H5 119.0 . . ?
C6 C5 C4 122.01(16) . . ?
C4 C5 H5 119.0 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.90(17) . . ?
C4 C3 H3 119.1 . . ?
C24 C22 P1 108.48(12) . . ?
C24 C22 C23 108.89(16) . . ?
C23 C22 P1 105.58(12) . . ?
C25 C22 P1 114.32(12) . . ?
C25 C22 C24 110.38(15) . . ?
C25 C22 C23 108.99(15) . . ?
C1 C6 C7 121.61(16) . . ?
C5 C6 C1 117.67(16) . . ?
C5 C6 C7 120.70(16) . . ?
C5 C4 C9 120.91(16) . . ?
C3 C4 C5 118.43(16) . . ?
C3 C4 C9 120.65(17) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
O4 C16 C17 107.25(14) . . ?
O4 C16 H16A 110.3 . . ?
O4 C16 H16B 110.3 . . ?
C17 C16 H16A 110.3 . . ?
C17 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?
O2 C14 H14A 109.4 . . ?
O2 C14 H14B 109.4 . . ?
O2 C14 C15 111.01(15) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 N2 1.6461(14) . ?
P1 C18 1.8670(18) . ?
P1 C11 1.7616(17) . ?
P1 C22 1.8655(17) . ?
O2 C12 1.326(2) . ?
O2 C14 1.463(2) . ?
O4 C13 1.364(2) . ?
O4 C16 1.4514(19) . ?
O1 C12 1.205(2) . ?
O3 C13 1.214(2) . ?
N1 N2 1.4115(19) . ?
N1 C1 1.442(2) . ?
N1 C10 1.323(2) . ?
C2 C1 1.399(2) . ?
C2 C3 1.394(2) . ?
C2 C8 1.505(2) . ?
C1 C6 1.399(2) . ?
C18 C20 1.532(2) . ?
C18 C21 1.536(2) . ?
C18 C19 1.534(2) . ?
C11 C13 1.437(2) . ?
C11 C10 1.401(2) . ?
C12 C10 1.503(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C5 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C22 C24 1.534(2) . ?
C22 C23 1.536(3) . ?
C22 C25 1.530(2) . ?
C6 C7 1.508(2) . ?
C4 C9 1.508(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C16 1.509(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.511(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
P1 C11 C13 O4 0.1(2) . . . . ?
P1 C11 C13 O3 -179.90(15) . . . . ?
P1 C11 C10 N1 -2.50(18) . . . . ?
P1 C11 C10 C12 173.70(14) . . . . ?
O2 C12 C10 N1 -82.03(19) . . . . ?
O2 C12 C10 C11 101.91(19) . . . . ?
O1 C12 C10 N1 95.5(2) . . . . ?
O1 C12 C10 C11 -80.5(2) . . . . ?
N1 C1 C6 C5 178.12(16) . . . . ?
N1 C1 C6 C7 -3.1(3) . . . . ?
N2 P1 C18 C20 65.74(14) . . . . ?
N2 P1 C18 C21 -168.71(12) . . . . ?
N2 P1 C18 C19 -50.92(14) . . . . ?
N2 P1 C11 C13 -170.78(17) . . . . ?
N2 P1 C11 C10 4.93(12) . . . . ?
N2 P1 C22 C24 -40.30(15) . . . . ?
N2 P1 C22 C23 76.28(13) . . . . ?
N2 P1 C22 C25 -163.94(13) . . . . ?
N2 N1 C1 C2 -81.13(19) . . . . ?
N2 N1 C1 C6 100.06(18) . . . . ?
N2 N1 C10 C11 -1.8(2) . . . . ?
N2 N1 C10 C12 -178.29(13) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C1 C6 C7 178.19(17) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C9 -179.48(17) . . . . ?
C1 N1 N2 P1 176.65(11) . . . . ?
C1 N1 C10 C11 -172.40(15) . . . . ?
C1 N1 C10 C12 11.1(2) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C18 P1 N2 N1 110.36(11) . . . . ?
C18 P1 C11 C13 73.96(18) . . . . ?
C18 P1 C11 C10 -110.33(12) . . . . ?
C18 P1 C22 C24 82.00(14) . . . . ?
C18 P1 C22 C23 -161.41(12) . . . . ?
C18 P1 C22 C25 -41.63(16) . . . . ?
C11 P1 N2 N1 -5.77(11) . . . . ?
C11 P1 C18 C20 172.48(12) . . . . ?
C11 P1 C18 C21 -61.96(15) . . . . ?
C11 P1 C18 C19 55.82(14) . . . . ?
C11 P1 C22 C24 -148.31(13) . . . . ?
C11 P1 C22 C23 -31.72(15) . . . . ?
C11 P1 C22 C25 88.05(15) . . . . ?
C13 O4 C16 C17 -178.95(14) . . . . ?
C13 C11 C10 N1 173.85(15) . . . . ?
C13 C11 C10 C12 -9.9(3) . . . . ?
C12 O2 C14 C15 -73.54(19) . . . . ?
C10 N1 N2 P1 5.42(17) . . . . ?
C10 N1 C1 C2 89.4(2) . . . . ?
C10 N1 C1 C6 -89.4(2) . . . . ?
C10 C11 C13 O4 -175.05(15) . . . . ?
C10 C11 C13 O3 5.0(3) . . . . ?
C3 C2 C1 N1 -179.26(15) . . . . ?
C3 C2 C1 C6 -0.5(3) . . . . ?
C22 P1 N2 N1 -126.29(11) . . . . ?
C22 P1 C18 C20 -55.55(14) . . . . ?
C22 P1 C18 C21 70.01(15) . . . . ?
C22 P1 C18 C19 -172.21(11) . . . . ?
C22 P1 C11 C13 -56.03(19) . . . . ?
C22 P1 C11 C10 119.68(12) . . . . ?
C6 C5 C4 C3 -0.3(3) . . . . ?
C6 C5 C4 C9 178.29(17) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C6 C7 -177.79(18) . . . . ?
C16 O4 C13 O3 2.8(2) . . . . ?
C16 O4 C13 C11 -177.16(14) . . . . ?
C14 O2 C12 O1 -3.3(2) . . . . ?
C14 O2 C12 C10 174.20(13) . . . . ?
C8 C2 C1 N1 -0.4(2) . . . . ?
C8 C2 C1 C6 178.42(17) . . . . ?
C8 C2 C3 C4 -177.66(17) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.4220 2.4635 10.6553 0.9941 0.0789 -0.0739
0.1215 -2.4463 -10.5132 -0.9881 -0.0785 0.1323
1.2142 2.2671 9.4425 0.9198 0.0735 -0.3855
1.3432 -2.4627 -10.8606 -0.9910 -0.0784 -0.1086
0.8423 -5.1683 4.4099 -0.1299 -0.9905 0.0460
-5.1298 0.4495 0.9401 0.0087 0.0781 0.9969
-2.4091 5.1988 -1.3959 0.3222 0.9127 0.2513
-1.3813 5.3569 -1.7217 0.3329 0.9421 0.0410
2.4792 -5.1782 1.3699 -0.3208 -0.9090 -0.2661
-0.5707 3.3480 -10.5345 -0.4777 0.8785 0.0089
-0.0167 -1.3505 12.5367 0.7937 -0.6083 0.0092
2.4005 0.2515 9.9584 0.7980 -0.2813 -0.5330
0.8434 -4.5131 -5.8748 -0.8223 -0.5658 0.0614
1.2377 4.2583 3.6395 0.6766 0.5793 -0.4544
-0.5590 3.3954 9.0065 0.9554 0.2837 -0.0814
