A radical path to 1,2-diphosphacyclobutenes.
Uttendorfer, Maria K.; Schneider, Lisa M.; Diener, Lukas S.; Hierlmeier, Gabriele; Balázs, Gábor; Wolf, Robert; Chemical communications (Cambridge, England) 61 (2025) 17464–17467; doi:10.1039/d5cc05221a

data_7135058
_publ_section_title
;
 A radical path to 1,2-diphosphacyclobutenes.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17464
_journal_page_last               17467
_journal_paper_doi               10.1039/d5cc05221a
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C46 H76 O2 P2'
_chemical_formula_sum            'C46 H76 O2 P2'
_chemical_formula_weight         723.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-06
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-09-01 deposited with the CCDC.	2025-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8760(2)
_cell_length_b                   14.46840(10)
_cell_length_c                   20.2954(2)
_cell_measurement_reflns_used    26782
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      74.9880
_cell_measurement_theta_min      4.1570
_cell_volume                     4515.68(8)
_computing_cell_refinement       'CrysAlisPro 1.171.43.36a (Rigaku OD, 2022)'
_computing_data_collection
'CrysAlisPro system (CCD 42.92a 64-bit (release 29-05-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.36a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     31.00  58.00   0.50    0.44    --   62.61-141.00  52.00   54
  2  \w     50.00  77.00   0.50    0.44    --   75.87-141.00  52.00   54
  3  \w     41.00  66.00   0.50    0.44    --   62.61-129.00-134.00   50
  4  \w     51.00 110.00   0.50    0.44    --   79.75-132.00-141.68  118
  5  \w     45.00  70.00   0.50    0.44    --   75.36-129.00-134.00   50
  6  \w     37.00  62.00   0.50    0.44    --   75.87-129.00-134.00   50
  7  \w     51.00 104.00   0.50    0.44    --   79.75-122.00 -84.05  106
  8  \w     46.00  87.00   0.50    0.44    --   79.75-108.00 -32.58   82
  9  \w     21.00  87.00   0.50    0.44    --   62.61-125.00   0.00  132
 10  \w     46.00  83.00   0.50    0.44    --   79.75 -99.00  16.82   74
 11  \w     41.00  90.00   0.50    0.44    --   79.75 -99.00  -9.20   98
 12  \w     72.00  99.00   0.50    0.44    --   79.75-114.00  54.30   54
 13  \w     40.00  67.00   0.50    0.44    --   79.75-114.00  54.30   54
 14  \w     21.00  61.00   0.50    0.44    --   62.61-125.00  90.00   80
 15  \w     31.00  70.00   0.50    0.44    --   62.61 -95.00 120.00   78
 16  \w     56.00  83.00   0.50    0.44    --   79.75 -87.00 101.16   54
 17  \w     27.00  69.00   0.50    0.44    --   62.61 -95.00  90.00   84
 18  \w     27.00  70.00   0.50    0.44    --   62.61 -95.00  30.00   86
 19  \w     26.00  71.00   0.50    0.44    --   62.61 -95.00-120.00   90
 20  \w     62.00 115.00   0.50    0.44    --   79.75  -3.00-107.98  106
 21  \w     40.00  69.00   0.50    0.44    --   79.75 -59.00  21.45   58
 22  \w     52.00  77.00   0.50    0.44    --   79.75 -77.00  24.84   50
 23  \w     40.00  65.00   0.50    0.44    --   79.75  -4.00  33.33   50
 24  \w     42.00  77.00   0.50    0.44    --   79.75  -4.00 -31.25   70
 25  \w     78.00 103.00   0.50    0.44    --   75.36 141.00 110.00   50
 26  \w     69.00  94.00   0.50    0.44    --   75.87 141.00 110.00   50
 27  \w     47.00  79.00   0.50    0.44    --   79.75  -4.00 155.01   64
 28  \w     47.00 114.00   0.50    0.44    --   79.75  -3.00  88.81  134
 29  \w     41.00  84.00   0.50    0.44    --   79.75  -4.00-129.43   86
 30  \w     25.00  54.00   0.50    0.44    --   62.61   0.00-180.00   58
 31  \w     33.00  61.00   0.50    0.44    --   22.00  46.00-154.66   56
 32  \w     64.00  90.00   0.50    0.44    --   54.00  57.00-170.11   52
 33  \w     73.00  98.00   0.50    0.44    --   62.00  47.00-136.65   50
 34  \w     94.00 124.00   0.50    0.44    --   79.75  41.00-146.97   60
 35  \w     97.00 123.00   0.50    0.44    --   79.75  50.00 111.36   52
 36  \w     93.00 122.00   0.50    0.44    --   79.75  42.00 178.94   58
 37  \w     91.00 127.00   0.50    0.44    --   79.75  36.00 162.96   72
 38  \w     91.00 117.00   0.50    0.44    --   79.75  23.00 157.16   52
 39  \w     99.00 124.00   0.50    0.44    --   79.75  13.00 118.05   50
 40  \w     66.00 121.00   0.50    0.44    --   79.75  23.00 123.11  110
 41  \w     59.00  92.00   0.50    0.44    --   79.75  13.00 118.05   66
 42  \w     47.00 110.00   0.50    0.44    --   79.75  18.00  59.40  126
 43  \w     33.00 107.00   0.50    0.44    --   62.61  15.00 -30.00  148
 44  \w     44.00 106.00   0.50    0.44    --   79.75   1.00  24.34  124
 45  \w     82.00 123.00   0.50    0.44    --   79.75  20.00 -36.79   82
 46  \w     95.00 121.00   0.50    0.44    --   79.75   8.00-110.47   52
 47  \w     59.00  90.00   0.50    0.44    --   79.75   8.00-110.47   62
 48  \w     75.00 100.00   0.50    0.44    --   62.61   0.00-180.00   50
 49  \w    -62.00 -36.00   0.50    0.44    --  -78.25  57.00 -21.46   52
 50  \w    -86.00 -61.00   0.50    0.44    --  -63.52 141.00 110.00   50
 51  \w    -99.00 -74.00   0.50    0.44    --  -76.46 141.00 110.00   50
 52  \w    -67.00 -42.00   0.50    0.44    --  -63.52 129.00 -62.00   50
 53  \w    -68.00 -40.00   0.50    0.44    --  -78.25 130.00 -71.06   56
 54  \w   -104.00 -60.00   0.50    0.44    --  -78.25 124.00  94.81   88
 55  \w    -94.00 -69.00   0.50    0.44    --  -76.46 129.00 -62.00   50
 56  \w    -91.00 -66.00   0.50    0.44    --  -73.68 129.00 -62.00   50
 57  \w    -75.00 -39.00   0.50    0.44    --  -78.25 126.00-161.02   72
 58  \w   -118.00 -88.00   0.50    0.44    --  -74.00 -40.00-153.82   60
 59  \w    -95.00 -69.00   0.50    0.44    --  -62.00 -71.00-152.77   52
 60  \w   -112.00 -86.00   0.50    0.44    --  -78.25 -75.00-155.68   52
 61  \w   -116.00 -91.00   0.50    0.44    --  -70.00 -42.00-176.10   50
 62  \w   -113.00 -88.00   0.50    0.44    --  -78.25 -75.00-119.37   50
 63  \w   -112.00 -82.00   0.50    0.44    --  -70.00 -55.00 135.03   60
 64  \w   -102.00 -77.00   0.50    0.44    --  -70.00 -75.00 178.40   50
 65  \w   -108.00 -82.00   0.50    0.44    --  -78.25-163.00 -60.25   52
 66  \w   -119.00 -94.00   0.50    0.44    --  -76.46-129.00-134.00   50
 67  \w    -80.00 -53.00   0.50    0.44    --  -78.25-163.00 -60.25   54
 68  \w   -109.00 -67.00   0.50    0.44    --  -73.68-141.00  52.00   84
 69  \w   -107.00 -81.00   0.50    0.44    --  -76.46-141.00  52.00   52
 70  \w   -105.00 -79.00   0.50    0.44    --  -78.25 -85.00 166.44   52
 71  \w   -108.00 -79.00   0.50    0.44    --  -78.25 -84.00 177.34   58
 72  \w   -112.00 -80.00   0.50    0.44    --  -78.25 -83.00 141.62   64
 73  \w   -106.00 -79.00   0.50    0.44    --  -78.25 -82.00 -64.76   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0643710000
_diffrn_orient_matrix_UB_12      -0.0739057000
_diffrn_orient_matrix_UB_13      -0.0120546000
_diffrn_orient_matrix_UB_21      -0.0384422000
_diffrn_orient_matrix_UB_22      0.0079151000
_diffrn_orient_matrix_UB_23      -0.0773387000
_diffrn_orient_matrix_UB_31      0.0664213000
_diffrn_orient_matrix_UB_32      0.0762590000
_diffrn_orient_matrix_UB_33      -0.0037339000
_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  0.0268
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            48145
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.213
_diffrn_reflns_theta_min         4.195
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.36a (Rigaku Oxford Diffraction, 2022)
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    1.063
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0414
_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/[\s^2^(Fo^2^)+(0.0612P)^2^+3.5447P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4298
_reflns_number_total             4626
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05221a2.cif
_cod_data_source_block           mu_lsd7_mc
_cod_depositor_comments
'Adding full bibliography for 7135058--7135059.cif.'
_cod_database_code               7135058
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'P C H O'
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.723
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C23(H23A,H23B,H23C), C5(H5A,H5B,H5C), C13(H13A,H13B,
 H13C), C3(H3A,H3B,H3C), C18(H18A,H18B,H18C), C15(H15A,H15B,H15C), C22(H22A,
 H22B,H22C), C4(H4A,H4B,H4C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C),
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              4894
_shelx_hkl_checksum              3580
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.745