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_7135059
_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         'C22 H28 P2 Se2'
_chemical_formula_sum            'C22 H28 P2 Se2'
_chemical_formula_weight         512.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-03
_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                 95.0240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9890(2)
_cell_length_b                   8.32050(10)
_cell_length_c                   18.1480(2)
_cell_measurement_reflns_used    10041
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      66.7800
_cell_measurement_theta_min      4.8750
_cell_volume                     2254.65(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.36a (Rigaku OD, 2022)'
_computing_data_collection
'CrysAlisPro system (CCD 42.90a 64-bit (release 14-04-2023))'
_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      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -41.00   6.00   1.00    1.00    --  -43.68  53.00  91.00   47
  2  \w     -6.00  68.00   1.00    1.00    --   43.68 -53.00 -52.00   74
  3  \w     22.00 113.00   1.00    1.00    --   43.68  53.00  91.00   91
  4  \w     40.00  65.00   1.00    3.36    --   86.50 -53.00 -52.00   25
  5  \w     73.00 100.00   1.00    3.36    --   86.50  53.00  91.00   27
  6  \w    -92.00 -66.00   1.00    3.36    --  -90.00 -53.00 -52.00   26
  7  \w   -143.00-109.00   1.00    3.36    --  -90.00 -53.00 -52.00   34
  8  \w    -47.00 -21.00   1.00    3.36    --  -90.00  53.00  91.00   26
  9  \w    -67.00 -38.00   1.00    1.00    --  -43.68 -53.00 -52.00   29
 10  \w     12.00  87.00   1.00    1.00    --   43.68-125.00 -60.00   75
 11  \w    -71.00 -28.00   1.00    3.36    --  -90.00 125.00-150.00   43
 12  \w    -93.00 -66.00   1.00    3.36    --  -90.00 -45.00-120.00   27
 13  \w   -110.00 -50.00   1.00    3.36    --  -90.00 125.00  90.00   60
 14  \w   -122.00 -17.00   1.00    3.36    --  -90.00  77.00  90.00  105
 15  \w   -162.00-104.00   1.00    3.36    --  -90.00-125.00 150.00   58
 16  \w    -49.00 -22.00   1.00    3.36    --  -90.00  61.00-120.00   27
 17  \w   -156.00-105.00   1.00    3.36    --  -90.00 -94.00 150.00   51
 18  \w   -111.00 -65.00   1.00    3.36    --  -90.00 125.00-180.00   46
 19  \w    -52.00 -27.00   1.00    3.36    --  -90.00 125.00-180.00   25
 20  \w   -159.00-125.00   1.00    3.36    --  -90.00 -61.00-120.00   34
 21  \w   -107.00 -66.00   1.00    3.36    --  -90.00 -61.00-120.00   41
 22  \w   -114.00 -55.00   1.00    3.36    --  -90.00  61.00-120.00   59
 23  \w   -156.00 -68.00   1.00    3.36    --  -90.00 -45.00   0.00   88
 24  \w   -135.00 -95.00   1.00    3.36    --  -90.00 -45.00-120.00   40
 25  \w   -146.00-100.00   1.00    3.36    --  -90.00 -45.00 -30.00   46
 26  \w    -93.00 -23.00   1.00    3.36    --  -90.00  77.00 -60.00   70
 27  \w   -123.00 -28.00   1.00    3.36    --  -90.00  15.00-120.00   95
 28  \w    -92.00 -25.00   1.00    3.36    --  -90.00  45.00-120.00   67
 29  \w   -168.00 -64.00   1.00    3.36    --  -90.00 -15.00  30.00  104
 30  \w   -103.00 -78.00   1.00    3.36    --  -90.00 125.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dualflex, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0772629000
_diffrn_orient_matrix_UB_12      -0.0707554000
_diffrn_orient_matrix_UB_13      -0.0515995000
_diffrn_orient_matrix_UB_21      0.0602332000
_diffrn_orient_matrix_UB_22      -0.1419995000
_diffrn_orient_matrix_UB_23      -0.0182005000
_diffrn_orient_matrix_UB_31      -0.0324583000
_diffrn_orient_matrix_UB_32      -0.0955030000
_diffrn_orient_matrix_UB_33      0.0652855000
_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  0.0476
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.768
_diffrn_reflns_theta_max         66.768
_diffrn_reflns_theta_min         4.893
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.456
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.388
_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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.146
_refine_diff_density_max         1.214
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0319
_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^)+(0.0470P)^2^+6.4765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0860
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1981
_reflns_number_total             2000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05221a2.cif
_cod_data_source_block           mu_lsc10_mi
_cod_depositor_comments
'Adding full bibliography for 7135058--7135059.cif.'
_cod_database_code               7135059
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C22  H28  P2  Se2'
_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:
 C7(H7), C11(H11), C8(H8), C10(H10), C9(H9)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_checksum              66529
_shelx_hkl_checksum              8383
_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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.700