Acyclic Diaminocarbene-Based Thiele, Chichibabin, and Müller Hydrocarbons
Maiti, Avijit; Chandra, Shubhadeep; Sarkar, Biprajit; Jana, Anukul; Chemical Science  (2020) –; doi:10.1039/D0SC03622F

data_1559246
_publ_section_title
;
 Acyclic Diaminocarbene-Based Thiele, Chichibabin, and M\"uller
 Hydrocarbons
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03622F
_journal_year                    2020
_chemical_formula_moiety         '2(C F3 O3 S), 2(C12 H22 N2)'
_chemical_formula_sum            'C26 H44 F6 N4 O6 S2'
_chemical_formula_weight         686.77
_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             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-12 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                67.708(6)
_cell_angle_beta                 77.216(5)
_cell_angle_gamma                89.130(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7348(5)
_cell_length_b                   13.5132(7)
_cell_length_c                   14.3175(9)
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    297.91(10)
_cell_measurement_theta_max      25.7230
_cell_measurement_theta_min      2.9490
_cell_volume                     1694.54(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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      air
_diffrn_ambient_temperature      297.91(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.861
_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    -33.00  42.00   0.50   50.51    --    7.10 -82.00-120.00  150
  2  \w     58.00  93.00   0.50   50.51    --    7.10  77.00 150.00   70
  3  \w     50.00  96.00   0.50   50.51    --    7.10  77.00 -60.00   92
  4  \w     51.00  95.00   0.50   50.51    --    7.10  77.00  30.00   88
  5  \w    -59.00 -12.00   0.50   50.51    --   -7.50 -82.00 150.00   94
  6  \w    -62.00  -3.00   0.50   50.51    --   -7.50 -82.00 -30.00  118
  7  \w    -41.00  17.00   0.50   50.51    --   -7.50 -82.00-180.00  116
  8  \w    -31.00  49.00   0.50   50.51    --   -7.50  57.00  30.00  160
  9  \w     13.00  52.00   0.50   50.51    --   -7.50  57.00 -90.00   78
 10  \w    -36.00  29.00   0.50   50.51    --   -7.50 -77.00  60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0439389000
_diffrn_orient_matrix_UB_12      0.0346058000
_diffrn_orient_matrix_UB_13      -0.0294006000
_diffrn_orient_matrix_UB_21      0.0514493000
_diffrn_orient_matrix_UB_22      0.0080528000
_diffrn_orient_matrix_UB_23      -0.0463674000
_diffrn_orient_matrix_UB_31      -0.0322055000
_diffrn_orient_matrix_UB_32      -0.0444366000
_diffrn_orient_matrix_UB_33      -0.0041190000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0874
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.028
_diffrn_reflns_theta_min         2.676
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         7789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0834
_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^)+(0.1044P)^2^+0.4461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3982
_reflns_number_total             7789
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj0927
_cod_database_code               1559246
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N S O F '
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C5(H5), C17(H17), C21(H21), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C), C12(H12A,H12B,
 H12C), C11(H11A,H11B,H11C), C7(H7A,H7B,H7C), C24(H24A,H24B,H24C), C6(H6A,H6B,
 H6C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C19(H19A,H19B,H19C), C22(H22A,
 H22B,H22C)
;
_shelx_res_checksum              91243
_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 2.264
_oxdiff_exptl_absorpt_empirical_full_min 0.540