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

data_1559253
_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         'C36 H52 N4'
_chemical_formula_sum            'C36 H52 N4'
_chemical_formula_weight         540.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-21
_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                90
_cell_angle_beta                 108.222(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.1170(8)
_cell_length_b                   9.2664(5)
_cell_length_c                   11.9686(7)
_cell_measurement_reflns_used    4524
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      27.2410
_cell_measurement_theta_min      2.8270
_cell_volume                     1592.49(16)
_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      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_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     20.00  46.00   0.50   83.00    --   13.40  47.00 -38.00   52
  2  \w     -7.00  19.00   0.50   83.00    --  -13.80  47.00 -38.00   52
  3  \w    -39.00   5.00   0.50   83.00    --  -13.80 -47.00 172.00   88
  4  \w     76.00 102.00   0.50   83.00    --   13.40  57.00  30.00   52
  5  \w    -22.00  52.00   0.50   83.00    --   13.40  57.00  30.00  148
  6  \w     50.00  78.00   0.50   83.00    --   13.40  77.00-120.00   56
  7  \w     15.00 103.00   0.50   83.00    --   13.40  57.00-150.00  176
  8  \w    -63.00 -37.00   0.50   83.00    --  -13.80 -82.00 120.00   52
  9  \w      3.00  28.00   0.50   83.00    --  -13.80 -82.00 120.00   50
 10  \w    -75.00  28.00   0.50   83.00    --  -13.80 -77.00 -30.00  206
;
_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      0.0334666000
_diffrn_orient_matrix_UB_12      0.0179303000
_diffrn_orient_matrix_UB_13      -0.0280735000
_diffrn_orient_matrix_UB_21      -0.0341265000
_diffrn_orient_matrix_UB_22      0.0403723000
_diffrn_orient_matrix_UB_23      -0.0427844000
_diffrn_orient_matrix_UB_31      0.0124403000
_diffrn_orient_matrix_UB_32      0.0625301000
_diffrn_orient_matrix_UB_33      0.0357049000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15048
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.655
_diffrn_reflns_theta_min         2.836
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41265
_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 green'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.5705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1625
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2584
_reflns_number_total             3681
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc03622f2.cif
_cod_data_source_block           aj1295
_cod_database_code               1559253
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N '
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.71
_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:
 C16(H16), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C7(H7), C6(H6), C10(H10), C9(H9)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              4552
_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 1.762
_oxdiff_exptl_absorpt_empirical_full_min 0.502