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

data_1559252
_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), C36 H52 N4'
_chemical_formula_sum            'C38 H52 F6 N4 O6 S2'
_chemical_formula_weight         838.95
_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
_audit_creation_date             2020-02-12
_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                86.324(3)
_cell_angle_beta                 89.745(3)
_cell_angle_gamma                69.232(3)
_cell_formula_units_Z            1
_cell_length_a                   8.2064(3)
_cell_length_b                   8.6379(3)
_cell_length_c                   18.5201(7)
_cell_measurement_reflns_used    6534
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.8760
_cell_measurement_theta_min      2.8600
_cell_volume                     1224.75(8)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.873
_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    -14.00  60.00   0.50   12.76    --    7.10  57.00 120.00  148
  2  \w     -5.00  96.00   0.50   12.76    --    7.10   0.00-180.00  202
  3  \w    -82.00 -19.00   0.50   12.76    --    7.10   0.00-180.00  126
  4  \w     -8.00  18.00   0.50   12.76    --   -7.50 -82.00   0.00   52
  5  \w    -84.00  21.00   0.50   12.76    --   -7.50 -57.00 -60.00  210
  6  \w    -76.00 -32.00   0.50   12.76    --   -7.50 -77.00 -90.00   88
  7  \w      4.00  29.00   0.50   12.76    --   -7.50 -77.00 -90.00   50
  8  \w    -66.00  17.00   0.50   12.76    --   -7.50 -57.00 150.00  166
;
_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      0.0469242000
_diffrn_orient_matrix_UB_12      -0.0268104000
_diffrn_orient_matrix_UB_13      -0.0318945000
_diffrn_orient_matrix_UB_21      0.0780155000
_diffrn_orient_matrix_UB_22      -0.0365054000
_diffrn_orient_matrix_UB_23      0.0209422000
_diffrn_orient_matrix_UB_31      -0.0161226000
_diffrn_orient_matrix_UB_32      -0.0754710000
_diffrn_orient_matrix_UB_33      0.0041951000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_unetI/netI     0.0860
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18070
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.871
_diffrn_reflns_theta_min         2.824
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56894
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5615
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0644
_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^)+(0.1095P)^2^+0.0199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.2047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3880
_reflns_number_total             5615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj1304
_cod_database_code               1559252
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O F S'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.36
_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. Restrained distances
 S1-C19 \\sim S1-C19A
 with sigma of 0.02
 F3-C19 \\sim F3A-C19A
 with sigma of 0.02
 F2-C19 \\sim F2A-C19A
 with sigma of 0.02
 F1-C19 \\sim F1A-C19A
 with sigma of 0.02
 S1-F3 \\sim S1-F3A
 with sigma of 0.04
 S1-F2 \\sim S1-F2A
 with sigma of 0.04
 S1-F1 \\sim S1-F1A
 with sigma of 0.04
 F3-F2 \\sim F3A-F2A
 with sigma of 0.04
 F3-F1 \\sim F3A-F1A
 with sigma of 0.04
 F2-F1 \\sim F2A-F1A
 with sigma of 0.04
 S1-O1 \\sim S1-O1A
 with sigma of 0.02
 S1-O2 \\sim S1-O2A
 with sigma of 0.02
 S1-O3 \\sim S1-O3A
 with sigma of 0.02
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C10-C9 \\sim C10A-C9A
 with sigma of 0.02
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C19)
Uanis(O1A) = Uanis(O1)
Uanis(O2) = Uanis(O2A)
Uanis(O3) = Uanis(O3A)
4. Rigid body (RIGU) restrains
 F3, O1, O2, O3, F2, F1, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2A, F1A, F3A, C19A, O3A, O2A, O1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C9A, C10A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F2A)=Sof(F1A)=Sof(F3A)=Sof(C19A)=1-FVAR(1)
 Sof(F3)=Sof(F2)=Sof(F1)=Sof(C19)=FVAR(1)
 Sof(O3A)=Sof(O2A)=Sof(O1A)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(O3)=FVAR(2)
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=1-FVAR(3)
 Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C12(H12)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C4(H4), C3(H3), C10(H10), C9(H9), C9A(H9A), C10A(H10A)
6.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C14(H14A,H14B,H14C), C11(H11A,H11B,
 H11C), C17(H17A,H17B,H17C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              46647
_shelx_fab_checksum              14195
_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 1.457
_oxdiff_exptl_absorpt_empirical_full_min 0.624