#------------------------------------------------------------------------------
#$Date: 2021-09-04 00:23:46 +0300 (Sat, 04 Sep 2021) $
#$Revision: 268443 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/90/4519020.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_4519020
loop_
_publ_author_name
'Huke, Cameron D.'
'Taylor, Laurence J.'
'Argent, Stephen P.'
'Kays, Deborah L.'
_publ_section_title
;
 Catalyst-free Hydrophosphinylation of Isocyanates and Isothiocyanates
 under Low-Added-Solvent Conditions
;
_journal_issue                   32
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_page_first              10704
_journal_page_last               10709
_journal_paper_doi               10.1021/acssuschemeng.1c02907
_journal_volume                  9
_journal_year                    2021
_chemical_formula_moiety         'C15 H16 N O2 P'
_chemical_formula_sum            'C15 H16 N O2 P'
_chemical_formula_weight         273.26
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_cell_angle_alpha                90.450(3)
_cell_angle_beta                 93.891(3)
_cell_angle_gamma                117.301(4)
_cell_formula_units_Z            4
_cell_length_a                   8.7838(4)
_cell_length_b                   8.7951(4)
_cell_length_c                   20.4442(8)
_cell_measurement_reflns_used    9535
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      72.4220
_cell_measurement_theta_min      4.3470
_cell_volume                     1398.88(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     -4.00  21.00   1.00    4.00    --   34.00  91.00 178.08   25
  2  ω     -5.00  20.00   1.00    4.00    --   34.00  94.00  87.64   25
  3  ω   -112.00 -13.00   1.00    4.00    --  -40.95 -57.00 150.00   99
  4  ω     58.00 101.00   1.00    4.00    --   40.95  38.00 -30.00   43
  5  ω    -29.00  69.00   1.00    4.00    --   40.95 -57.00  30.00   98
  6  ω     25.00  56.00   1.00    4.00    --   40.95  38.00 -30.00   31
  7  ω     28.00  97.00   1.00    4.00    --   40.95-125.00 -60.00   69
  8  ω      7.00  32.00   1.00    4.00    --   42.00  84.00 -29.01   25
  9  ω     16.00  41.00   1.00    4.00    --   50.00  82.00-118.59   25
 10  ω     16.00  41.00   1.00    4.00    --   50.00  81.00-168.19   25
 11  ω     16.00  41.00   1.00    4.00    --   50.00  81.00  31.84   25
 12  ω     16.00  41.00   1.00    4.00    --   50.00  82.00 -38.62   25
 13  ω     16.00  41.00   1.00    4.00    --   50.00  82.00  41.65   25
 14  ω     16.00  41.00   1.00    4.00    --   50.00  81.00-133.72   25
 15  ω     16.00  41.00   1.00    4.00    --   50.00  82.00 128.30   25
 16  ω     23.00  50.00   1.00    4.00    --   54.00  71.00  17.80   27
 17  ω     64.00 128.00   1.00    4.00    --   54.00  71.00  17.80   64
 18  ω     25.00  52.00   1.00    4.00    --   54.00  74.00 102.46   27
 19  ω     96.00 122.00   1.00    4.00    --   54.00  74.00 102.46   26
 20  ω     92.00 131.00   1.00    4.00    --   58.00  74.00  54.49   39
 21  ω     28.00  55.00   1.00    4.00    --   58.00  74.00  54.49   27
 22  ω     30.00  61.00   1.00    4.00    --   62.00  74.00 108.47   31
 23  ω     33.00  60.00   1.00    4.00    --   62.00  71.00 159.17   27
 24  ω    109.00 134.00   1.00    4.00    --   62.00  74.00 108.47   25
 25  ω     97.00 134.00   1.00    4.00    --   62.00  71.00 159.17   37
 26  ω     34.00  61.00   1.00    4.00    --   66.00  74.00 -77.72   27
 27  ω     36.00  64.00   1.00    4.00    --   66.00  64.00-104.30   28
 28  ω     37.00  76.00   1.00    4.00    --   66.00  68.00   8.39   39
 29  ω     39.00  73.00   1.00    4.00    --   70.00  73.00 175.70   34
 30  ω     43.00  69.00   1.00    4.00    --   70.00  54.00 155.70   26
 31  ω     44.00  76.00   1.00   16.00    --   74.00  66.00  49.23   32
 32  ω    101.00 149.00   1.00   16.00    --   74.00  73.00 -61.02   48
 33  ω     42.00  69.00   1.00   16.00    --   74.00  73.00 -61.02   27
 34  ω    121.00 148.00   1.00   16.00    --   78.00  64.00 -39.95   27
 35  ω     51.00  84.00   1.00   16.00    --   78.00  64.00 -39.95   33
 36  ω     52.00  91.00   1.00   16.00    --   82.00  65.00-142.70   39
 37  ω     58.00  86.00   1.00   16.00    --   86.00  62.00  93.02   28
 38  ω     75.00 171.00   1.00   16.00    --  104.05  61.00  90.00   96
 39  ω    129.00 173.00   1.00   16.00    --  104.05 125.00   0.00   44
 40  ω     31.00 112.00   1.00   16.00    --  104.05-125.00 -30.00   81
 41  ω     76.00 103.00   1.00   16.00    --  104.05  61.00  30.00   27
 42  ω     68.00 111.00   1.00   16.00    --  104.05-125.00  30.00   43
 43  ω     75.00 172.00   1.00   16.00    --  104.05  61.00   0.00   97
 44  ω     75.00 171.00   1.00   16.00    --  104.05  61.00-150.00   96
 45  ω     75.00 159.00   1.00   16.00    --  104.05  61.00 120.00   84
 46  ω    116.00 141.00   1.00   16.00    --  104.05  61.00  60.00   25
 47  ω     75.00 102.00   1.00   16.00    --  104.05  61.00  60.00   27
 48  ω     30.00  85.00   1.00   16.00    --  104.05 -77.00 -30.00   55
 49  ω    114.00 175.00   1.00   16.00    --  104.05  61.00 150.00   61
 50  ω     83.00 112.00   1.00   16.00    --  104.05-125.00-120.00   29
 51  ω     76.00 102.00   1.00   16.00    --  104.05  61.00 150.00   26
 52  ω     32.00  81.00   1.00   16.00    --  104.05-125.00-120.00   49
 53  ω     75.00 176.00   1.00   16.00    --  104.05  61.00 -90.00  101
 54  ω    117.00 144.00   1.00   16.00    --  104.05  61.00 -30.00   27
 55  ω     75.00 104.00   1.00   16.00    --  104.05  61.00 -30.00   29
 56  ω    129.00 156.00   1.00   16.00    --  104.05  61.00-180.00   27
 57  ω    112.00 175.00   1.00   16.00    --  104.05  61.00  30.00   63
 58  ω     28.00 117.00   1.00   16.00    --  104.05 -77.00  90.00   89
 59  ω     75.00 114.00   1.00   16.00    --  104.05  61.00-180.00   39
 60  ω     76.00 154.00   1.00   16.00    --  104.05  61.00-120.00   78
 61  ω    119.00 176.00   1.00   16.00    --  104.05  61.00 -60.00   57
 62  ω     75.00 107.00   1.00   16.00    --  104.05  61.00 -60.00   32
 63  ω     24.00 107.00   1.00   16.00    --  104.05 -94.00  60.00   83
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0398021000
_diffrn_orient_matrix_UB_12      0.1501229000
_diffrn_orient_matrix_UB_13      0.0136117000
_diffrn_orient_matrix_UB_21      0.1900405000
_diffrn_orient_matrix_UB_22      0.1141018000
_diffrn_orient_matrix_UB_23      0.0236856000
_diffrn_orient_matrix_UB_31      0.0391497000
_diffrn_orient_matrix_UB_32      0.0580998000
_diffrn_orient_matrix_UB_33      -0.0704835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7807
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.753
_diffrn_reflns_theta_min         4.339
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.721
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method 'Recystallised from ethanol'
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7807
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0356
_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)+(0.0688P)²+0.2094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1059
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6791
_reflns_number_total             7807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sc1c02907_si_002.cif
_cod_data_source_block           ochdkb
_cod_original_cell_volume        1398.88(11)
_cod_database_code               4519020
_nottingham_internal_coll_name   OCHDKB
_nottingham_internal_coll_number 18736
_nottingham_internal_coll_client CH/DLK
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '16.00, 4.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pczlt
_nottingham_internal_coll_date   20/07/2020
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 06/08/2020
_nottingham_internal_process_user pczlt
_nottingham_internal_solution_date 06/08/2020
_nottingham_internal_solution_user pczlt
_nottingham_internal_refinement_date 06/08/2020
_nottingham_internal_refinement_user pczlt
_nottingham_internal_self_archive_date 16/02/2021
_nottingham_internal_self_validation_date 16/02/2021
_nottingham_internal_self_validation_user pcxch6
_nottingham_internal_validation_date 17/02/2021
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date 17/02/2021
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H16N1O2P
_chemical_oxdiff_usercomment
'OCHDKB #18736 GVB-1803 CH/DLK fomblin micromount'
_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   0.877
_shelx_estimated_absorpt_t_min   0.641
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5320(9)
 0.4680(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
 N2-H2A
 0.88 with sigma of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C4(H4), C23(H23), C18(H18), C9(H9), C24(H24), C3(H3),
 C21(H21), C27(H27), C12(H12), C6(H6), C17(H17), C25(H25), C10(H10), C26(H26),
 C19(H19), C20(H20), C11(H11), C5(H5)
4.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C15(H15A,H15B,H15C)
;
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id OCHDKB
_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.763
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 0.55361(7) 0.52615(7) 0.33486(2) 0.02380(13) Uani 1 1 d . . . . .
P2 P 0.98466(7) 0.91713(7) 0.16532(2) 0.02353(13) Uani 1 1 d . . . . .
O3 O 0.9655(2) 0.8711(2) 0.23520(7) 0.0308(3) Uani 1 1 d . . . . .
O4 O 0.7954(2) 0.7926(2) 0.05020(7) 0.0312(3) Uani 1 1 d . . . . .
O1 O 0.5865(2) 0.5498(2) 0.26452(7) 0.0320(4) Uani 1 1 d . . . . .
O2 O 0.6895(2) 0.7144(2) 0.44770(6) 0.0300(3) Uani 1 1 d . . . . .
N2 N 0.6767(2) 0.6408(2) 0.13915(8) 0.0256(4) Uani 1 1 d D . . . .
H2A H 0.684(3) 0.637(3) 0.1815(9) 0.031 Uiso 1 1 d D U . . .
N1 N 0.8398(2) 0.8281(2) 0.35842(8) 0.0260(4) Uani 1 1 d D . . . .
H1 H 0.844(3) 0.813(3) 0.3167(9) 0.031 Uiso 1 1 d D U . . .
C13 C 0.7112(3) 0.7095(3) 0.38900(9) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.5965(3) 0.3249(3) 0.43341(10) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.600081 0.407557 0.464514 0.033 Uiso 1 1 calc R U . . .
C28 C 0.7985(3) 0.7678(3) 0.10946(9) 0.0242(4) Uani 1 1 d . . . . .
C1 C 0.5710(3) 0.3439(3) 0.36647(10) 0.0248(4) Uani 1 1 d . . . . .
C29 C 0.5206(3) 0.5093(3) 0.10351(10) 0.0286(4) Uani 1 1 d . . . . .
H29A H 0.490845 0.559436 0.064545 0.034 Uiso 1 1 calc R U . . .
H29B H 0.424383 0.471426 0.132147 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2688(3) 0.4388(3) 0.40834(10) 0.0278(4) Uani 1 1 d . . . . .
H8 H 0.317101 0.386744 0.437927 0.033 Uiso 1 1 calc R U . . .
C22 C 1.1674(3) 0.9085(3) 0.13408(9) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.6099(3) 0.0634(3) 0.40917(12) 0.0363(5) Uani 1 1 d . . . . .
H4 H 0.623090 -0.032513 0.423732 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3508(3) 0.5138(3) 0.35248(10) 0.0251(4) Uani 1 1 d . . . . .
C23 C 1.1827(3) 0.8918(3) 0.06716(10) 0.0267(4) Uani 1 1 d . . . . .
H23 H 1.097234 0.890526 0.035750 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9765(3) 0.9817(3) 0.39339(10) 0.0297(5) Uani 1 1 d . . . . .
H14A H 0.928889 1.014010 0.430511 0.036 Uiso 1 1 calc R U . . .
H14B H 1.016839 1.077644 0.363255 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0560(3) 1.3648(3) 0.08372(13) 0.0379(5) Uani 1 1 d . . . . .
H18 H 1.102347 1.426700 0.046003 0.045 Uiso 1 1 calc R U . . .
C9 C 0.1160(3) 0.4409(3) 0.42031(11) 0.0336(5) Uani 1 1 d . . . . .
H9 H 0.058873 0.388416 0.457963 0.040 Uiso 1 1 calc R U . . .
C24 C 1.3227(3) 0.8771(3) 0.04672(11) 0.0316(5) Uani 1 1 d . . . . .
H24 H 1.332188 0.864094 0.001226 0.038 Uiso 1 1 calc R U . . .
C3 C 0.6167(3) 0.1852(3) 0.45447(11) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.635178 0.172786 0.500017 0.037 Uiso 1 1 calc R U . . .
C21 C 0.9218(3) 1.1869(3) 0.19450(11) 0.0366(5) Uani 1 1 d . . . . .
H21 H 0.877190 1.126805 0.232745 0.044 Uiso 1 1 calc R U . . .
C27 C 1.2939(3) 0.9108(3) 0.17985(11) 0.0306(5) Uani 1 1 d . . . . .
H27 H 1.283704 0.921462 0.225428 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9933(3) 1.1215(3) 0.15022(10) 0.0264(4) Uani 1 1 d . . . . .
C12 C 0.2780(3) 0.5887(3) 0.30930(11) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.331992 0.637071 0.270620 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5652(3) 0.2218(3) 0.32103(11) 0.0324(5) Uani 1 1 d . . . . .
H6 H 0.548539 0.234328 0.275386 0.039 Uiso 1 1 calc R U . . .
C17 C 1.0612(3) 1.2119(3) 0.09459(10) 0.0303(5) Uani 1 1 d . . . . .
H17 H 1.110757 1.168624 0.064307 0.036 Uiso 1 1 calc R U . . .
C25 C 1.4491(3) 0.8812(3) 0.09215(12) 0.0355(5) Uani 1 1 d . . . . .
H25 H 1.545578 0.872765 0.077713 0.043 Uiso 1 1 calc R U . . .
C10 C 0.0462(3) 0.5182(3) 0.37815(12) 0.0373(5) Uani 1 1 d . . . . .
H10 H -0.057436 0.520214 0.387298 0.045 Uiso 1 1 calc R U . . .
C26 C 1.4348(3) 0.8976(4) 0.15874(12) 0.0380(6) Uani 1 1 d . . . . .
H26 H 1.521261 0.899869 0.189877 0.046 Uiso 1 1 calc R U . . .
C30 C 0.5416(4) 0.3564(3) 0.08172(13) 0.0419(6) Uani 1 1 d . . . . .
H30A H 0.639792 0.393900 0.054836 0.063 Uiso 1 1 calc R U . . .
H30B H 0.437083 0.275107 0.055825 0.063 Uiso 1 1 calc R U . . .
H30C H 0.561706 0.300665 0.120319 0.063 Uiso 1 1 calc R U . . .
C15 C 1.1271(3) 0.9556(3) 0.41922(13) 0.0411(6) Uani 1 1 d . . . . .
H15A H 1.181464 0.934100 0.382369 0.062 Uiso 1 1 calc R U . . .
H15B H 1.087133 0.857206 0.447399 0.062 Uiso 1 1 calc R U . . .
H15C H 1.210790 1.058422 0.444701 0.062 Uiso 1 1 calc R U . . .
C19 C 0.9834(4) 1.4273(3) 0.12782(14) 0.0431(6) Uani 1 1 d . . . . .
H19 H 0.980164 1.532211 0.120093 0.052 Uiso 1 1 calc R U . . .
C20 C 0.9156(4) 1.3391(4) 0.18299(14) 0.0467(7) Uani 1 1 d . . . . .
H20 H 0.865087 1.382440 0.212812 0.056 Uiso 1 1 calc R U . . .
C11 C 0.1266(4) 0.5930(4) 0.32249(12) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.078750 0.646747 0.293580 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5840(4) 0.0817(3) 0.34288(12) 0.0393(6) Uani 1 1 d . . . . .
H5 H 0.578943 -0.002140 0.312029 0.047 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
4 0 5 0.0415
1 1 -5 0.1409
-1 -1 5 0.1409
-4 -1 -4 0.0525
-1 1 5 0.1046
-2 -2 -5 0.0399
0 0 1 0.1315
1 -1 -1 0.0791
3 -5 -1 0.0525
-3 5 1 0.0362
2 3 5 0.0297
1 0 -5 0.1352
-4 0 -5 0.0415
5 -3 3 0.0485
0 1 -5 0.1340
1 -5 -4 0.0394
-3 0 -5 0.0306
-4 5 2 0.0377
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
O1 P1 C13 112.87(9) . . ?
O1 P1 C1 112.90(9) . . ?
O1 P1 C7 113.28(10) . . ?
C1 P1 C13 104.19(9) . . ?
C7 P1 C13 103.14(10) . . ?
C7 P1 C1 109.66(10) . . ?
O3 P2 C28 112.84(9) . . ?
O3 P2 C22 112.48(9) . . ?
O3 P2 C16 113.41(10) . . ?
C22 P2 C28 104.53(9) . . ?
C16 P2 C28 103.06(10) . . ?
C16 P2 C22 109.77(10) . . ?
C28 N2 H2A 120.2(18) . . ?
C28 N2 C29 122.65(17) . . ?
C29 N2 H2A 117.0(18) . . ?
C13 N1 H1 118.7(18) . . ?
C13 N1 C14 122.09(17) . . ?
C14 N1 H1 119.2(18) . . ?
O2 C13 P1 119.66(16) . . ?
O2 C13 N1 125.83(19) . . ?
N1 C13 P1 114.50(14) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.9(2) . . ?
O4 C28 P2 119.85(16) . . ?
O4 C28 N2 125.7(2) . . ?
N2 C28 P2 114.45(14) . . ?
C2 C1 P1 122.72(16) . . ?
C2 C1 C6 119.8(2) . . ?
C6 C1 P1 117.46(16) . . ?
N2 C29 H29A 109.2 . . ?
N2 C29 H29B 109.2 . . ?
N2 C29 C30 112.24(19) . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C9 C8 C7 119.4(2) . . ?
C23 C22 P2 122.91(16) . . ?
C27 C22 P2 117.34(15) . . ?
C27 C22 C23 119.7(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C8 C7 P1 122.59(17) . . ?
C12 C7 P1 117.68(17) . . ?
C12 C7 C8 119.7(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
N1 C14 H14A 109.1 . . ?
N1 C14 H14B 109.1 . . ?
N1 C14 C15 112.61(19) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.5(2) . . ?
C25 C24 H24 119.8 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C16 120.3(2) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 C22 120.0(2) . . ?
C26 C27 H27 120.0 . . ?
C21 C16 P2 118.02(18) . . ?
C21 C16 C17 119.5(2) . . ?
C17 C16 P2 122.39(17) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.7(2) . . ?
C5 C6 H6 120.2 . . ?
C18 C17 C16 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.1(2) . . ?
C26 C25 H25 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.5(2) . . ?
C19 C20 H20 120.2 . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
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
P1 O1 1.4835(14) . ?
P1 C13 1.860(2) . ?
P1 C1 1.799(2) . ?
P1 C7 1.796(2) . ?
P2 O3 1.4874(14) . ?
P2 C28 1.859(2) . ?
P2 C22 1.800(2) . ?
P2 C16 1.794(2) . ?
O4 C28 1.233(2) . ?
O2 C13 1.231(2) . ?
N2 H2A 0.866(18) . ?
N2 C28 1.328(3) . ?
N2 C29 1.464(3) . ?
N1 H1 0.869(18) . ?
N1 C13 1.334(3) . ?
N1 C14 1.469(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.396(3) . ?
C2 C3 1.388(3) . ?
C1 C6 1.396(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.507(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.395(3) . ?
C8 C9 1.389(3) . ?
C22 C23 1.397(3) . ?
C22 C27 1.395(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(3) . ?
C4 C5 1.382(4) . ?
C7 C12 1.393(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.386(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.506(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.385(3) . ?
C18 C19 1.383(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(3) . ?
C3 H3 0.9500 . ?
C21 H21 0.9500 . ?
C21 C16 1.395(3) . ?
C21 C20 1.386(4) . ?
C27 H27 0.9500 . ?
C27 C26 1.392(3) . ?
C16 C17 1.397(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.389(4) . ?
C17 H17 0.9500 . ?
C25 H25 0.9500 . ?
C25 C26 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C26 H26 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.382(4) . ?
C20 H20 0.9500 . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
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
N2 H2A O1 0.866(18) 1.95(2) 2.750(2) 152(3) . yes
N1 H1 O3 0.869(18) 1.98(2) 2.778(2) 151(2) . 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
P1 C1 C6 C5 177.81(19) . . . . ?
P1 C7 C12 C11 -175.88(19) . . . . ?
P2 C22 C23 C24 -176.68(17) . . . . ?
P2 C22 C27 C26 177.5(2) . . . . ?
P2 C16 C17 C18 176.51(18) . . . . ?
O3 P2 C28 O4 178.49(17) . . . . ?
O3 P2 C28 N2 -0.9(2) . . . . ?
O3 P2 C22 C23 158.94(18) . . . . ?
O3 P2 C22 C27 -18.0(2) . . . . ?
O3 P2 C16 C21 -22.8(2) . . . . ?
O3 P2 C16 C17 160.24(18) . . . . ?
O1 P1 C13 O2 173.04(17) . . . . ?
O1 P1 C13 N1 -5.93(19) . . . . ?
O1 P1 C1 C2 160.36(17) . . . . ?
O1 P1 C1 C6 -17.0(2) . . . . ?
O1 P1 C7 C8 158.78(18) . . . . ?
O1 P1 C7 C12 -23.7(2) . . . . ?
C13 P1 C1 C2 37.5(2) . . . . ?
C13 P1 C1 C6 -139.82(18) . . . . ?
C13 P1 C7 C8 -78.9(2) . . . . ?
C13 P1 C7 C12 98.63(19) . . . . ?
C13 N1 C14 C15 90.4(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C28 P2 C22 C23 36.2(2) . . . . ?
C28 P2 C22 C27 -140.82(18) . . . . ?
C28 P2 C16 C21 99.49(19) . . . . ?
C28 P2 C16 C17 -77.4(2) . . . . ?
C28 N2 C29 C30 90.8(2) . . . . ?
C1 P1 C13 O2 -64.13(19) . . . . ?
C1 P1 C13 N1 116.91(16) . . . . ?
C1 P1 C7 C8 31.7(2) . . . . ?
C1 P1 C7 C12 -150.84(19) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C6 C5 C4 -0.6(4) . . . . ?
C29 N2 C28 P2 -179.50(15) . . . . ?
C29 N2 C28 O4 1.2(3) . . . . ?
C8 C7 C12 C11 1.7(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C22 P2 C28 O4 -59.0(2) . . . . ?
C22 P2 C28 N2 121.64(16) . . . . ?
C22 P2 C16 C21 -149.59(18) . . . . ?
C22 P2 C16 C17 33.5(2) . . . . ?
C22 C23 C24 C25 -0.9(3) . . . . ?
C22 C27 C26 C25 -0.3(4) . . . . ?
C7 P1 C13 O2 50.42(19) . . . . ?
C7 P1 C13 N1 -128.55(16) . . . . ?
C7 P1 C1 C2 -72.3(2) . . . . ?
C7 P1 C1 C6 110.34(18) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C7 C12 C11 C10 -1.7(4) . . . . ?
C23 C22 C27 C26 0.4(3) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C14 N1 C13 P1 -179.83(16) . . . . ?
C14 N1 C13 O2 1.3(3) . . . . ?
C18 C19 C20 C21 0.6(4) . . . . ?
C9 C8 C7 P1 177.04(17) . . . . ?
C9 C8 C7 C12 -0.4(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C24 C25 C26 C27 -0.3(4) . . . . ?
C3 C2 C1 P1 -177.06(17) . . . . ?
C3 C2 C1 C6 0.2(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C21 C16 C17 C18 -0.4(3) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
C16 P2 C28 O4 55.8(2) . . . . ?
C16 P2 C28 N2 -123.60(17) . . . . ?
C16 P2 C22 C23 -73.8(2) . . . . ?
C16 P2 C22 C27 109.23(18) . . . . ?
C16 C21 C20 C19 -1.1(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C19 C18 C17 C16 -0.2(4) . . . . ?
C20 C21 C16 P2 -176.0(2) . . . . ?
C20 C21 C16 C17 1.0(4) . . . . ?
C5 C4 C3 C2 0.4(4) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5320(9)
2 0.4680(9)
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
3.9986 0.0021 5.0009 -0.0908 0.8786 -0.1958
0.9991 0.9988 -5.0012 0.0421 0.1854 0.4496
-0.9991 -0.9988 5.0012 -0.0421 -0.1854 -0.4496
-3.9985 -1.0019 -4.0009 -0.0457 -0.9690 0.0673
-0.9992 1.0014 5.0018 0.2582 0.0428 -0.3335
-1.9994 -2.0019 -5.0018 -0.2890 -0.7269 0.1580
0.0001 0.0003 1.0003 0.0137 0.0237 -0.0705
0.9995 -1.0002 -1.0007 -0.2036 0.0521 0.0516
2.9988 -5.0002 -1.0022 -0.8836 -0.0244 -0.1025
-2.9988 5.0002 1.0022 0.8836 0.0244 0.1025
1.9994 3.0020 5.0021 0.4392 0.8410 -0.0999
0.9991 -0.0013 -5.0015 -0.1080 0.0713 0.3916
-3.9986 -0.0021 -5.0009 0.0908 -0.8786 0.1958
4.9982 -2.9986 2.9993 -0.6083 0.6788 -0.1899
-0.0005 0.9986 -5.0011 0.0819 -0.0046 0.4105
0.9995 -5.0014 -4.0028 -0.8451 -0.4755 0.0307
-2.9991 -0.0019 -5.0010 0.0510 -0.6886 0.2350
-3.9983 5.0003 2.0026 0.9371 -0.1419 -0.0072
