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_7710155
_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_absolute_configuration ad
_chemical_formula_moiety         'I, 2(C H Cl3), C46 H52 N2 P'
_chemical_formula_sum            'C48 H54 Cl6 I N2 P'
_chemical_formula_weight         1029.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-21
_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                90
_cell_angle_beta                 100.423(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6946(3)
_cell_length_b                   23.0494(5)
_cell_length_c                   11.1709(3)
_cell_measurement_reflns_used    19773
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      31.7930
_cell_measurement_theta_min      2.7510
_cell_volume                     2455.00(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 (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      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_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      4.00  70.00   1.00    5.00    --   16.92-123.00 -32.98   66
  2  \w      7.00  82.00   1.00    5.00    --   16.92  38.00   0.00   75
  3  \w     -2.00  83.00   1.00    5.00    --   16.92  38.00-120.00   85
  4  \w      0.00  88.00   1.00    5.00    --   16.92  38.00 150.00   88
  5  \w      0.00  67.00   1.00    5.00    --   16.92-118.00  21.06   67
  6  \w    -53.00  31.00   1.00    5.00    --   16.92 -38.00  60.00   84
  7  \w    -44.00  42.00   1.00    5.00    --   16.92 -57.00-180.00   86
  8  \w    -38.00  13.00   1.00    5.00    --  -17.08 -77.00-150.00   51
  9  \w    -75.00 -41.00   1.00    5.00    --  -17.08 131.00  37.89   34
 10  \w    -63.00   7.00   1.00    5.00    --  -17.08 -57.00   0.00   70
;
_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      -0.0733137000
_diffrn_orient_matrix_UB_12      -0.0044334000
_diffrn_orient_matrix_UB_13      -0.0170810000
_diffrn_orient_matrix_UB_21      0.0120944000
_diffrn_orient_matrix_UB_22      -0.0208252000
_diffrn_orient_matrix_UB_23      -0.0437105000
_diffrn_orient_matrix_UB_31      0.0033009000
_diffrn_orient_matrix_UB_32      -0.0222240000
_diffrn_orient_matrix_UB_33      0.0443453000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            52929
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         2.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
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    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.148
_refine_diff_density_max         1.249
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 5655 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.063(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         14359
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0289P)^2^+1.7938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                13037
_reflns_number_total             14359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt01314b2.cif
_cod_data_source_block           compound_3a
_cod_original_cell_volume        2454.99(11)
_cod_database_code               7710155
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C48H54Cl6IN2P
_diffrn_oxdiff_digest_frames
;
01396a4b458bb8663f697c4625692d0e6f00706ed41
;
_diffrn_oxdiff_digest_hkl
;
013f7d9f69303ea4d73c96f77f9bcbc3b81891
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.97
_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. Uiso/Uaniso restraints and constraints
Uanis(Cl6A) = Uanis(Cl6B) = Uanis(Cl5B) = Uanis(Cl5A)
3. Others
 Sof(Cl5B)=Sof(Cl6B)=Sof(H48A)=1-FVAR(1)
 Sof(Cl5A)=Sof(Cl6A)=Sof(H48)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C47(H47), C48(H48), C48(H48A), C17(H17), C20(H20), C41(H41), C44(H44)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32),
  C33(H33), C34(H34), C37(H37), C38(H38), C39(H39)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,
 H45B,H45C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              6012
_olex2_date_sample_data_collection 2020-07-21
_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 1.200
_oxdiff_exptl_absorpt_empirical_full_min 0.841