#------------------------------------------------------------------------------
#$Date: 2020-04-28 23:32:13 +0300 (Tue, 28 Apr 2020) $
#$Revision: 251242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038306.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_4038306
loop_
_publ_author_name
'Del Corte, Xabier'
'López-Francés, Adrián'
'Maestro, Aitor'
'Martinez de Marigorta, Edorta'
'Palacios, Francisco'
'Vicario, Javier'
_publ_section_title
;
 Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and
 Fluorine-Derived γ-Lactam Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00280
_journal_year                    2020
_chemical_formula_moiety         'C25 H33 N2 O4 P'
_chemical_formula_sum            'C25 H33 N2 O4 P'
_chemical_formula_weight         456.5
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-30T21:29:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.667(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7968(4)
_cell_length_b                   20.6201(13)
_cell_length_c                   15.4863(7)
_cell_measurement_reflns_used    2382
_cell_measurement_temperature    150.6(9)
_cell_measurement_theta_max      66.203
_cell_measurement_theta_min      3.582
_cell_volume                     2419.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -79.00  11.00   1.00    3.25    --  -42.38 108.00  28.00   90
  2  ω     -6.00  86.00   1.00    3.25    --   42.38-108.00 -68.00   92
  3  ω     33.00 112.00   1.00   12.00    --  107.93-108.00 -68.00   79
  4  ω    112.00 138.00   1.00   12.00    --  107.93 108.00  28.00   26
  5  ω      5.00  30.00   1.00    3.25    --   40.00  86.00  62.41   25
  6  ω   -108.00 -56.00   1.00    3.25    --  -42.38 -77.00 -90.00   52
  7  ω   -109.00 -21.00   1.00    3.25    --  -42.38 -38.00   0.00   88
  8  ω    -67.00 -14.00   1.00    3.25    --  -42.38 -57.00 -90.00   53
  9  ω    -37.00 -10.00   1.00    3.25    --  -42.38 -77.00 -90.00   27
 10  ω     20.00  72.00   1.00    3.25    --   42.38  38.00  30.00   52
 11  ω     15.00  42.00   1.00    3.25    --   44.00  61.00  84.60   27
 12  ω     56.00 115.00   1.00    3.25    --   44.00  61.00  84.60   59
 13  ω      7.00  32.00   1.00    3.25    --   44.00  89.00 -44.67   25
 14  ω     18.00  43.00   1.00    3.25    --   52.00  82.00   3.24   25
 15  ω     18.00  43.00   1.00    3.25    --   52.00  82.00-108.91   25
 16  ω     18.00  44.00   1.00    3.25    --   52.00  81.00-155.29   26
 17  ω     19.00  45.00   1.00    3.25    --   52.00  80.00 168.97   26
 18  ω     19.00  44.00   1.00    3.25    --   52.00  80.00 -69.46   25
 19  ω     19.00  44.00   1.00    3.25    --   52.00  80.00  98.35   25
 20  ω     18.00  43.00   1.00    3.25    --   52.00  82.00 132.94   25
 21  ω     18.00  43.00   1.00    3.25    --   52.00  82.00  57.66   25
 22  ω     29.00  56.00   1.00    3.25    --   60.00  77.00  24.82   27
 23  ω     31.00  72.00   1.00    3.25    --   64.00  77.00 -57.24   41
 24  ω     31.00  58.00   1.00    3.25    --   64.00  77.00  48.73   27
 25  ω     33.00  59.00   1.00    3.25    --   64.00  75.00  86.18   26
 26  ω     36.00  62.00   1.00    3.25    --   68.00  77.00 -23.06   26
 27  ω     36.00  72.00   1.00    3.25    --   68.00  76.00 177.33   36
 28  ω     40.00  67.00   1.00    3.25    --   72.00  77.00-130.53   27
 29  ω     39.00  66.00   1.00    3.25    --   72.00  77.00 106.31   27
 30  ω     93.00 130.00   1.00    3.25    --   72.00  77.00 106.31   37
 31  ω     40.00  66.00   1.00    3.25    --   72.00  75.00 -97.58   26
 32  ω     39.00  65.00   1.00    3.25    --   72.00  77.00-160.76   26
 33  ω     46.00  73.00   1.00   12.00    --   76.00  65.00  68.12   27
 34  ω     44.00  70.00   1.00   12.00    --   76.00  76.00 119.77   26
 35  ω     51.00  78.00   1.00   12.00    --   80.00  68.00 -17.43   27
 36  ω     48.00  74.00   1.00   12.00    --   80.00  74.00 -50.34   26
 37  ω    119.00 152.00   1.00   12.00    --   80.00  74.00 -50.34   33
 38  ω     49.00 122.00   1.00   12.00    --   80.00  72.00 144.57   73
 39  ω     49.00 152.00   1.00   12.00    --   80.00  71.00 -82.31  103
 40  ω     53.00  80.00   1.00   12.00    --   84.00  70.00 -46.02   27
 41  ω     54.00  89.00   1.00   12.00    --   84.00  66.00   2.17   35
 42  ω     53.00  80.00   1.00   12.00    --   84.00  69.00-159.70   27
 43  ω    121.00 148.00   1.00   12.00    --   84.00  66.00   2.17   27
 44  ω    132.00 158.00   1.00   12.00    --   84.00  70.00 -46.02   26
 45  ω     58.00  85.00   1.00   12.00    --   88.00  65.00  80.89   27
 46  ω     60.00  87.00   1.00   12.00    --   92.00  73.00  39.55   27
 47  ω     63.00 151.00   1.00   12.00    --   96.00  77.00 151.13   88
 48  ω     31.00  99.00   1.00   12.00    --  107.93 -94.00-150.00   68
 49  ω     27.00 104.00   1.00   12.00    --  107.93 -94.00 150.00   77
 50  ω     81.00 141.00   1.00   12.00    --  107.93  61.00  90.00   60
 51  ω     75.00 146.00   1.00   12.00    --  107.93  77.00  90.00   71
 52  ω     81.00 109.00   1.00   12.00    --  107.93  61.00 -90.00   28
 53  ω    109.00 157.00   1.00   12.00    --  107.93  77.00 -30.00   48
 54  ω     75.00 155.00   1.00   12.00    --  107.93  77.00 120.00   80
 55  ω     75.00 105.00   1.00   12.00    --  107.93  77.00 -30.00   30
 56  ω     75.00 147.00   1.00   12.00    --  107.93  77.00   0.00   72
 57  ω     40.00  74.00   1.00   12.00    --  107.93 -45.00-120.00   34
 58  ω     79.00 106.00   1.00   12.00    --  107.93  61.00   0.00   27
 59  ω     81.00 109.00   1.00   12.00    --  107.93  61.00-150.00   28
 60  ω     75.00 148.00   1.00   12.00    --  107.93  77.00-150.00   73
 61  ω     75.00 149.00   1.00   12.00    --  107.93  77.00-120.00   74
 62  ω     26.00 105.00   1.00   12.00    --  107.93 -94.00 -30.00   79
 63  ω     31.00 108.00   1.00   12.00    --  107.93 -94.00  60.00   77
 64  ω     75.00 147.00   1.00   12.00    --  107.93  77.00 -60.00   72
 65  ω     75.00 148.00   1.00   12.00    --  107.93  77.00 -90.00   73
 66  ω     76.00 103.00   1.00   12.00    --  107.93  77.00  60.00   27
 67  ω     35.00  75.00   1.00   12.00    --  107.93 -45.00-180.00   40
 68  ω     40.00  65.00   1.00   12.00    --  107.93 -45.00 -60.00   25
 69  ω     42.00  68.00   1.00   12.00    --  107.93 -45.00  60.00   26
 70  ω    107.00 152.00   1.00   12.00    --  107.93  77.00-180.00   45
 71  ω     91.00 116.00   1.00   12.00    --  107.93-125.00  60.00   25
 72  ω     41.00  77.00   1.00   12.00    --  107.93-125.00  60.00   36
 73  ω     75.00 101.00   1.00   12.00    --  107.93  77.00-180.00   26
 74  ω     79.00 146.00   1.00   12.00    --  107.93  77.00  30.00   67
 75  ω     36.00  75.00   1.00   12.00    --  107.93 -45.00  30.00   39
 76  ω     35.00  68.00   1.00   12.00    --  107.93 -45.00 120.00   33
;
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1606711
_diffrn_orient_matrix_UB_12      0.0445122
_diffrn_orient_matrix_UB_13      0.004747
_diffrn_orient_matrix_UB_21      -0.1060599
_diffrn_orient_matrix_UB_22      0.0580014
_diffrn_orient_matrix_UB_23      0.022547
_diffrn_orient_matrix_UB_31      0.0656441
_diffrn_orient_matrix_UB_32      -0.0152015
_diffrn_orient_matrix_UB_33      0.0997748
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.2437
_diffrn_reflns_av_unetI/netI     0.4341
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47617
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.993
_diffrn_reflns_theta_min         3.636
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.271
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       needle
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0420P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1665
_reflns_Friedel_coverage         0
_reflns_number_gt                2545
_reflns_number_total             4500
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00280_si_004.cif
_cod_data_source_block           a20190280_xd323
_cod_database_code               4038306
loop_
_symmetry_equiv_pos_as_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 0.51643(13) 0.66043(5) 0.76467(7) 0.0345(3) Uani 1 1 d . . . . .
O1 O 0.7646(3) 0.64882(15) 0.44136(18) 0.0434(7) Uani 1 1 d . . . . .
O2 O 0.3336(3) 0.69624(14) 0.7470(2) 0.0429(7) Uani 1 1 d . . . . .
O3 O 0.5218(4) 0.61637(14) 0.84818(18) 0.0420(7) Uani 1 1 d . . . . .
O4 O 0.6691(3) 0.70402(13) 0.77171(18) 0.0384(7) Uani 1 1 d . . . . .
N1 N 0.6610(4) 0.61791(16) 0.5633(2) 0.0320(7) Uani 1 1 d . . . . .
N2 N 0.4529(4) 0.74041(16) 0.4241(2) 0.0382(8) Uani 1 1 d . . . . .
H2 H 0.401401 0.749378 0.368487 0.046 Uiso 1 1 calc R . . . .
C1 C 0.6495(5) 0.64726(19) 0.4825(3) 0.0329(9) Uani 1 1 d . . . . .
C2 C 0.4587(5) 0.67322(19) 0.4518(3) 0.0328(9) Uani 1 1 d . . . . .
C3 C 0.3802(5) 0.65735(19) 0.5301(2) 0.0323(8) Uani 1 1 d . . . . .
C4 C 0.4985(5) 0.62518(19) 0.5909(3) 0.0316(9) Uani 1 1 d . . . . .
C5 C 0.8114(5) 0.58076(19) 0.6092(3) 0.0328(9) Uani 1 1 d . . . . .
C6 C 0.9152(5) 0.6026(2) 0.6888(3) 0.0365(9) Uani 1 1 d . . . . .
H6 H 0.892685 0.643531 0.712056 0.044 Uiso 1 1 calc R . . . .
C7 C 1.0530(5) 0.5639(2) 0.7347(3) 0.0425(10) Uani 1 1 d . . . . .
H7 H 1.123403 0.578747 0.789819 0.051 Uiso 1 1 calc R . . . .
C8 C 1.0901(5) 0.5046(2) 0.7022(3) 0.0437(11) Uani 1 1 d . . . . .
C9 C 0.9882(5) 0.4847(2) 0.6194(3) 0.0448(10) Uani 1 1 d . . . . .
H9 H 1.014872 0.445048 0.594084 0.054 Uiso 1 1 calc R . . . .
C10 C 0.8484(5) 0.5225(2) 0.5741(3) 0.0383(9) Uani 1 1 d . . . . .
H10 H 0.777967 0.508155 0.518732 0.046 Uiso 1 1 calc R . . . .
C11 C 1.2351(6) 0.4621(3) 0.7546(4) 0.0632(15) Uani 1 1 d . . . . .
H11A H 1.184253 0.429568 0.787361 0.095 Uiso 1 1 calc GR . . . .
H11B H 1.319909 0.488828 0.79652 0.095 Uiso 1 1 calc GR . . . .
H11C H 1.295389 0.440288 0.713868 0.095 Uiso 1 1 calc GR . . . .
C12 C 0.3698(5) 0.6323(2) 0.3703(3) 0.0401(10) Uani 1 1 d . . . . .
H12A H 0.247686 0.646835 0.34799 0.06 Uiso 1 1 calc GR . . . .
H12B H 0.370556 0.586527 0.387458 0.06 Uiso 1 1 calc GR . . . .
H12C H 0.434596 0.637492 0.323715 0.06 Uiso 1 1 calc GR . . . .
C13 C 0.5230(5) 0.79159(19) 0.4794(3) 0.0333(9) Uani 1 1 d . . . . .
C14 C 0.5014(5) 0.8542(2) 0.4449(3) 0.0392(10) Uani 1 1 d . . . . .
H14 H 0.437827 0.860836 0.385247 0.047 Uiso 1 1 calc R . . . .
C15 C 0.5723(5) 0.9073(2) 0.4974(3) 0.0447(10) Uani 1 1 d . . . . .
H15 H 0.559074 0.949433 0.471923 0.054 Uiso 1 1 calc R . . . .
C16 C 0.6617(5) 0.9001(2) 0.5859(3) 0.0396(10) Uani 1 1 d . . . . .
C17 C 0.6809(5) 0.8378(2) 0.6187(3) 0.0389(9) Uani 1 1 d . . . . .
H17 H 0.740909 0.831347 0.679002 0.047 Uiso 1 1 calc R . . . .
C18 C 0.6167(5) 0.7842(2) 0.5675(3) 0.0422(10) Uani 1 1 d . . . . .
H18 H 0.636496 0.742047 0.592585 0.051 Uiso 1 1 calc R . . . .
C19 C 0.7356(6) 0.9576(2) 0.6438(3) 0.0499(11) Uani 1 1 d . . . . .
H19A H 0.66253 0.966029 0.686069 0.075 Uiso 1 1 calc GR . . . .
H19B H 0.735286 0.995953 0.606268 0.075 Uiso 1 1 calc GR . . . .
H19C H 0.856792 0.948133 0.676322 0.075 Uiso 1 1 calc GR . . . .
C20 C 0.1962(5) 0.6761(2) 0.5311(3) 0.0454(11) Uani 1 1 d . . . . .
H20A H 0.162578 0.655327 0.581519 0.068 Uiso 1 1 calc GR . . . .
H20B H 0.115706 0.662129 0.475589 0.068 Uiso 1 1 calc GR . . . .
H20C H 0.189177 0.723357 0.53668 0.068 Uiso 1 1 calc GR . . . .
C21 C 0.4862(5) 0.59931(19) 0.6797(2) 0.0323(9) Uani 1 1 d . . . . .
H21A H 0.576756 0.565203 0.698303 0.039 Uiso 1 1 calc R . . . .
H21B H 0.369013 0.578926 0.673794 0.039 Uiso 1 1 calc R . . . .
C22 C 0.3149(6) 0.7664(2) 0.7465(4) 0.0626(14) Uani 1 1 d . . . . .
H22A H 0.379915 0.785879 0.70519 0.075 Uiso 1 1 calc R . . . .
H22B H 0.364425 0.783904 0.80671 0.075 Uiso 1 1 calc R . . . .
C23 C 0.1252(6) 0.7825(2) 0.7176(3) 0.0597(13) Uani 1 1 d . . . . .
H23A H 0.077394 0.765256 0.657829 0.09 Uiso 1 1 calc GR . . . .
H23B H 0.110473 0.829743 0.716938 0.09 Uiso 1 1 calc GR . . . .
H23C H 0.061966 0.763306 0.759024 0.09 Uiso 1 1 calc GR . . . .
C24 C 0.5187(6) 0.6471(2) 0.9331(3) 0.0492(11) Uani 1 1 d . . . . .
H24A H 0.400075 0.665247 0.930725 0.059 Uiso 1 1 calc R . . . .
H24B H 0.605611 0.682933 0.94568 0.059 Uiso 1 1 calc R . . . .
C25 C 0.5636(7) 0.5967(3) 1.0044(3) 0.0654(15) Uani 1 1 d . . . . .
H25A H 0.479608 0.560696 0.990222 0.098 Uiso 1 1 calc GR . . . .
H25B H 0.557053 0.615833 1.061512 0.098 Uiso 1 1 calc GR . . . .
H25C H 0.683379 0.580611 1.008274 0.098 Uiso 1 1 calc GR . . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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
1 -3 9 0.0248
4 -1 -7 0.1305
0 1 0 0.0023
0 -13 0 0.0306
-1 3 -9 0.0232
-5 1 3 0.1295
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
O2 P1 O3 105.18(16) . . ?
O2 P1 C21 104.20(17) . . ?
O3 P1 C21 99.81(17) . . ?
O4 P1 O2 114.19(16) . . ?
O4 P1 O3 115.27(16) . . ?
O4 P1 C21 116.45(17) . . ?
C22 O2 P1 123.7(3) . . ?
C24 O3 P1 119.0(3) . . ?
C1 N1 C4 110.6(3) . . ?
C1 N1 C5 123.7(3) . . ?
C4 N1 C5 125.5(3) . . ?
C2 N2 H2 117.8 . . ?
C13 N2 H2 117.8 . . ?
C13 N2 C2 124.4(3) . . ?
O1 C1 N1 126.2(3) . . ?
O1 C1 C2 127.2(4) . . ?
N1 C1 C2 106.4(3) . . ?
N2 C2 C1 112.5(3) . . ?
N2 C2 C3 116.9(3) . . ?
N2 C2 C12 107.8(3) . . ?
C3 C2 C1 102.7(3) . . ?
C3 C2 C12 110.4(3) . . ?
C12 C2 C1 106.0(3) . . ?
C4 C3 C2 109.3(3) . . ?
C4 C3 C20 129.2(4) . . ?
C20 C3 C2 121.5(3) . . ?
N1 C4 C21 119.2(3) . . ?
C3 C4 N1 110.8(3) . . ?
C3 C4 C21 130.0(3) . . ?
C6 C5 N1 120.3(3) . . ?
C10 C5 N1 119.4(3) . . ?
C10 C5 C6 120.3(4) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(4) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 C9 118.1(4) . . ?
C7 C8 C11 120.9(4) . . ?
C9 C8 C11 120.9(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 120.3(4) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 118.4(3) . . ?
N2 C13 C18 124.0(4) . . ?
C14 C13 C18 117.6(4) . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(4) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C19 122.1(4) . . ?
C17 C16 C15 116.6(4) . . ?
C17 C16 C19 121.3(4) . . ?
C16 C17 H17 118.6 . . ?
C16 C17 C18 122.8(4) . . ?
C18 C17 H17 118.6 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
P1 C21 H21A 108.9 . . ?
P1 C21 H21B 108.9 . . ?
C4 C21 P1 113.4(3) . . ?
C4 C21 H21A 108.9 . . ?
C4 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
O2 C22 H22A 110 . . ?
O2 C22 H22B 110 . . ?
O2 C22 C23 108.5(4) . . ?
H22A C22 H22B 108.4 . . ?
C23 C22 H22A 110 . . ?
C23 C22 H22B 110 . . ?
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 . . ?
O3 C24 H24A 110.1 . . ?
O3 C24 H24B 110.1 . . ?
O3 C24 C25 108.1(4) . . ?
H24A C24 H24B 108.4 . . ?
C25 C24 H24A 110.1 . . ?
C25 C24 H24B 110.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 O2 1.571(3) . ?
P1 O3 1.573(3) . ?
P1 O4 1.475(3) . ?
P1 C21 1.797(4) . ?
O1 C1 1.217(4) . ?
O2 C22 1.453(5) . ?
O3 C24 1.466(5) . ?
N1 C1 1.374(5) . ?
N1 C4 1.438(5) . ?
N1 C5 1.440(5) . ?
N2 H2 0.88 . ?
N2 C2 1.448(5) . ?
N2 C13 1.387(5) . ?
C1 C2 1.547(5) . ?
C2 C3 1.517(5) . ?
C2 C12 1.540(5) . ?
C3 C4 1.328(5) . ?
C3 C20 1.490(5) . ?
C4 C21 1.500(5) . ?
C5 C6 1.381(5) . ?
C5 C10 1.376(6) . ?
C6 H6 0.95 . ?
C6 C7 1.390(6) . ?
C7 H7 0.95 . ?
C7 C8 1.380(6) . ?
C8 C9 1.400(6) . ?
C8 C11 1.506(6) . ?
C9 H9 0.95 . ?
C9 C10 1.388(6) . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C14 1.391(6) . ?
C13 C18 1.396(6) . ?
C14 H14 0.95 . ?
C14 C15 1.398(6) . ?
C15 H15 0.95 . ?
C15 C16 1.391(6) . ?
C16 C17 1.377(6) . ?
C16 C19 1.515(6) . ?
C17 H17 0.95 . ?
C17 C18 1.383(6) . ?
C18 H18 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.99 . ?
C21 H21B 0.99 . ?
C22 H22A 0.99 . ?
C22 H22B 0.99 . ?
C22 C23 1.479(6) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 H24A 0.99 . ?
C24 H24B 0.99 . ?
C24 C25 1.497(7) . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
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 O2 C22 C23 173.6(3) . . . . ?
P1 O3 C24 C25 -168.1(3) . . . . ?
O1 C1 C2 N2 -53.6(5) . . . . ?
O1 C1 C2 C3 179.8(4) . . . . ?
O1 C1 C2 C12 63.9(5) . . . . ?
O2 P1 O3 C24 -63.2(3) . . . . ?
O2 P1 C21 C4 78.8(3) . . . . ?
O3 P1 O2 C22 121.3(4) . . . . ?
O3 P1 C21 C4 -172.6(3) . . . . ?
O4 P1 O2 C22 -6.1(4) . . . . ?
O4 P1 O3 C24 63.5(3) . . . . ?
O4 P1 C21 C4 -47.9(3) . . . . ?
N1 C1 C2 N2 130.4(3) . . . . ?
N1 C1 C2 C3 3.8(4) . . . . ?
N1 C1 C2 C12 -112.1(3) . . . . ?
N1 C4 C21 P1 99.0(4) . . . . ?
N1 C5 C6 C7 176.0(3) . . . . ?
N1 C5 C10 C9 -177.2(4) . . . . ?
N2 C2 C3 C4 -126.9(4) . . . . ?
N2 C2 C3 C20 54.1(5) . . . . ?
N2 C13 C14 C15 -178.8(4) . . . . ?
N2 C13 C18 C17 -179.3(4) . . . . ?
C1 N1 C4 C3 1.0(5) . . . . ?
C1 N1 C4 C21 -177.1(3) . . . . ?
C1 N1 C5 C6 113.7(4) . . . . ?
C1 N1 C5 C10 -67.9(5) . . . . ?
C1 C2 C3 C4 -3.3(4) . . . . ?
C1 C2 C3 C20 177.8(4) . . . . ?
C2 N2 C13 C14 -177.3(4) . . . . ?
C2 N2 C13 C18 3.7(6) . . . . ?
C2 C3 C4 N1 1.6(5) . . . . ?
C2 C3 C4 C21 179.4(4) . . . . ?
C3 C4 C21 P1 -78.7(5) . . . . ?
C4 N1 C1 O1 -179.2(4) . . . . ?
C4 N1 C1 C2 -3.1(4) . . . . ?
C4 N1 C5 C6 -71.7(5) . . . . ?
C4 N1 C5 C10 106.7(4) . . . . ?
C5 N1 C1 O1 -3.8(6) . . . . ?
C5 N1 C1 C2 172.3(3) . . . . ?
C5 N1 C4 C3 -174.2(4) . . . . ?
C5 N1 C4 C21 7.7(5) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C5 C10 C9 1.2(6) . . . . ?
C6 C7 C8 C9 2.0(6) . . . . ?
C6 C7 C8 C11 -177.4(4) . . . . ?
C7 C8 C9 C10 -3.2(6) . . . . ?
C8 C9 C10 C5 1.6(6) . . . . ?
C10 C5 C6 C7 -2.4(6) . . . . ?
C11 C8 C9 C10 176.2(4) . . . . ?
C12 C2 C3 C4 109.4(4) . . . . ?
C12 C2 C3 C20 -69.5(5) . . . . ?
C13 N2 C2 C1 -62.4(5) . . . . ?
C13 N2 C2 C3 56.1(5) . . . . ?
C13 N2 C2 C12 -178.9(3) . . . . ?
C13 C14 C15 C16 -2.0(6) . . . . ?
C14 C13 C18 C17 1.6(6) . . . . ?
C14 C15 C16 C17 1.7(6) . . . . ?
C14 C15 C16 C19 -178.7(4) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C13 -2.0(6) . . . . ?
C18 C13 C14 C15 0.3(6) . . . . ?
C19 C16 C17 C18 -179.3(4) . . . . ?
C20 C3 C4 N1 -179.6(4) . . . . ?
C20 C3 C4 C21 -1.7(7) . . . . ?
C21 P1 O2 C22 -134.2(4) . . . . ?
C21 P1 O3 C24 -170.9(3) . . . . ?
