Crystalline phosphino-functionalized mesoionic olefins (p-MIOs)
Merschel, Arne; Vishnevskiy, Yury V.; Neumann, Beate; Stammler, Georg; Ghadwal, Rajendra S.; Dalton Transactions  (2022) –; doi:10.1039/D2DT01314B

data_7710157
_publ_section_title
;
 Crystalline phosphino-functionalized mesoionic olefins (p-MIOs)
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01314B
_journal_year                    2022
_chemical_formula_moiety
'C52 H56 B Cl N2 P, C6 H5 B Cl3, 0.35(C H2 Cl2)'
_chemical_formula_sum            'C58.35 H61.71 B2 Cl4.7 N2 P'
_chemical_formula_weight         1010.44
_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             2021-02-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-11-12 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.088(3)
_cell_angle_beta                 75.067(3)
_cell_angle_gamma                80.567(3)
_cell_formula_units_Z            2
_cell_length_a                   11.6389(3)
_cell_length_b                   15.0221(5)
_cell_length_c                   15.9346(5)
_cell_measurement_reflns_used    28912
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3960
_cell_measurement_theta_min      2.8430
_cell_volume                     2646.59(15)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -59.00  28.00   1.00    3.86    --  -38.50  38.00  30.00   87
  2  \w    -59.00  32.00   1.00    3.86    --  -38.50  38.00 120.00   91
  3  \w    -68.00 -15.00   1.00    3.86    --  -38.50 -66.00  37.06   53
  4  \w    -58.00  31.00   1.00    3.86    --  -38.50  38.00-150.00   89
  5  \w    -54.00  27.00   1.00    3.86    --  -38.50  38.00 -60.00   81
  6  \w     19.00  99.00   1.00    3.86    --   42.70  57.00-120.00   80
  7  \w     22.00  59.00   1.00    3.86    --   42.70  38.00   0.00   37
  8  \w     54.00  89.00   1.00    3.86    --   42.70-125.00  90.00   35
  9  \w     13.00  42.00   1.00    3.86    --   42.70  78.00 126.29   29
 10  \w     42.00  87.00   1.00    3.86    --   42.70-125.00 -90.00   45
 11  \w     56.00 101.00   1.00    3.86    --   42.70  57.00  30.00   45
 12  \w     11.00  39.00   1.00    3.86    --   42.70  82.00-162.63   28
 13  \w     12.00  42.00   1.00    3.86    --   42.70  80.00 -35.69   30
 14  \w     11.00  42.00   1.00    3.86    --   42.70  82.00 -83.24   31
 15  \w     18.00  46.00   1.00    3.86    --   42.70  57.00  30.00   28
 16  \w     18.00  98.00   1.00    3.86    --   42.70  57.00 150.00   80
 17  \w     64.00  91.00   1.00    3.86    --   42.70  38.00 120.00   27
 18  \w     24.00  57.00   1.00    3.86    --   42.70  38.00 120.00   33
 19  \w     12.00  42.00   1.00    3.86    --   42.70  79.00  51.60   30
 20  \w     85.00 178.00   1.00   14.50    --  111.00  59.00 140.02   93
 21  \w     85.00 111.00   1.00   14.50    --  111.00  59.00 -66.32   26
 22  \w     83.00 110.00   1.00   14.50    --  111.00  69.00 103.12   27
 23  \w     90.00 169.00   1.00   14.50    --  111.00  45.00 -60.00   79
 24  \w     83.00 113.00   1.00   14.50    --  111.00  69.00 -63.36   30
 25  \w    114.00 141.00   1.00   14.50    --  111.00 -77.00   0.00   27
 26  \w     89.00 122.00   1.00   14.50    --  111.00  45.00  30.00   33
 27  \w     31.00 106.00   1.00   14.50    --  111.00 -94.00-120.00   75
 28  \w     83.00 122.00   1.00   14.50    --  111.00  70.00 -47.25   39
 29  \w     42.00 111.00   1.00   14.50    --  111.00-125.00-180.00   69
 30  \w     42.00 113.00   1.00   14.50    --  111.00-125.00-120.00   71
 31  \w     47.00  90.00   1.00   14.50    --  111.00 -77.00   0.00   43
 32  \w     85.00 178.00   1.00   14.50    --  111.00  61.00-131.14   93
 33  \w     87.00 114.00   1.00   14.50    --  111.00  55.00 175.95   27
 34  \w     85.00 174.00   1.00   14.50    --  111.00  62.00  76.17   89
 35  \w     38.00 109.00   1.00   14.50    --  111.00-111.00  99.02   71
 36  \w    120.00 178.00   1.00   14.50    --  111.00  68.00  25.85   58
 37  \w    117.00 152.00   1.00   14.50    --  111.00  71.00-149.03   35
 38  \w     83.00 109.00   1.00   14.50    --  111.00  68.00  25.85   26
 39  \w     85.00 162.00   1.00   14.50    --  111.00  61.00 120.00   77
 40  \w    122.00 174.00   1.00   14.50    --  111.00  61.00-180.00   52
 41  \w     87.00 113.00   1.00   14.50    --  111.00  54.00  26.45   26
 42  \w     85.00 111.00   1.00   14.50    --  111.00  61.00-120.00   26
 43  \w    137.00 178.00   1.00   14.50    --  111.00  61.00-120.00   41
 44  \w     32.00  79.00   1.00   14.50    --  111.00 -94.00   0.00   47
 45  \w     82.00 107.00   1.00   14.50    --  111.00 -94.00   0.00   25
 46  \w     82.00 114.00   1.00   14.50    --  111.00  71.00-149.03   32
 47  \w     90.00 115.00   1.00   14.50    --  111.00  45.00  60.00   25
 48  \w     85.00 111.00   1.00   14.50    --  111.00  61.00   0.00   26
 49  \w     85.00 112.00   1.00   14.50    --  111.00  61.00  90.00   27
 50  \w    142.00 178.00   1.00   14.50    --  111.00  71.00  87.38   36
 51  \w     85.00 120.00   1.00   14.50    --  111.00  61.00-180.00   35
 52  \w     89.00 172.00   1.00   14.50    --  111.00  45.00   0.00   83
 53  \w     82.00 108.00   1.00   14.50    --  111.00  72.00-161.38   26
 54  \w     82.00 108.00   1.00   14.50    --  111.00  73.00-103.64   26
 55  \w     85.00 163.00   1.00   14.50    --  111.00  61.00 -30.00   78
 56  \w     89.00 115.00   1.00   14.50    --  111.00  45.00-150.00   26
 57  \w    145.00 170.00   1.00   14.50    --  111.00  56.00 168.11   25
 58  \w    123.00 156.00   1.00   14.50    --  111.00  61.00  60.00   33
 59  \w     85.00 111.00   1.00   14.50    --  111.00  61.00  60.00   26
 60  \w    146.00 175.00   1.00   14.50    --  111.00  49.00 -93.75   29
 61  \w     33.00 107.00   1.00   14.50    --  111.00 -94.00 -60.00   74
 62  \w     85.00 111.00   1.00   14.50    --  111.00  61.00 150.00   26
 63  \w     42.00  91.00   1.00   14.50    --  111.00-125.00-150.00   49
 64  \w     88.00 114.00   1.00   14.50    --  111.00  49.00 -93.75   26
 65  \w     86.00 112.00   1.00   14.50    --  111.00  56.00 168.11   26
 66  \w     87.00 114.00   1.00   14.50    --  111.00  54.00-151.61   27
 67  \w     82.00 108.00   1.00   14.50    --  111.00  71.00  87.38   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0557516000
_diffrn_orient_matrix_UB_12      0.0436250000
_diffrn_orient_matrix_UB_13      0.0866438000
_diffrn_orient_matrix_UB_21      0.1254108000
_diffrn_orient_matrix_UB_22      0.0162882000
_diffrn_orient_matrix_UB_23      0.0046654000
_diffrn_orient_matrix_UB_31      -0.0172437000
_diffrn_orient_matrix_UB_32      0.0933387000
_diffrn_orient_matrix_UB_33      -0.0505038000
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51224
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.949
_diffrn_reflns_theta_min         2.880
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.944
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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    1.268
_exptl_crystal_description       needle
_exptl_crystal_F_000             1062
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     640
_refine_ls_number_reflns         11005
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+1.2151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.0974
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10119
_reflns_number_total             11005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01314b2.cif
_cod_data_source_block           compound_6
_cod_original_cell_volume        2646.59(14)
_cod_original_formula_sum        'C58.35 H61.71 B2 Cl4.70 N2 P'
_cod_database_code               7710157
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C58H59BCl5N3P
_diffrn_oxdiff_digest_frames
;
01ced80f71f6de9a81ac79caa7e3a2148003175e156
;
_diffrn_oxdiff_digest_hkl
;
0142e3c8a626cbbdbac0989ce6b908049d42f6
;
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl6-C59 = Cl5-C59
 1.771 with sigma of 0.01
 Cl6-Cl5
 2.916 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Cl5 \\sim Cl6 \\sim C59: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
4. Rigid body (RIGU) restrains
 Cl5, Cl6, C59
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl5)=Sof(Cl6)=Sof(C59)=Sof(H59A)=Sof(H59B)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C59(H59A,H59B)
6.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40),
  C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C48(H48), C49(H49),
 C50(H50), C51(H51), C52(H52), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58)
6.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_shelx_res_checksum              18131
_olex2_date_sample_data_collection 2021-02-18
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.858