Synthesis, structural characterization, and coordination chemistry of imidazole-based alkylidene ketenes.
Feuerstein, Wolfram; Varava, Paul; Fadaei-Tirani, Farzaneh; Scopelliti, Rosario; Severin, Kay; Chemical communications (Cambridge, England) 57 (2021) 11509–11512; doi:10.1039/d1cc05161j

data_7129131
_publ_section_title
;
 Synthesis, structural characterization, and coordination chemistry of
 imidazole-based alkylidene ketenes.
;
_journal_issue                   87
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11509
_journal_page_last               11512
_journal_paper_doi               10.1039/d1cc05161j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C30 H40 N2 O2'
_chemical_formula_sum            'C30 H40 N2 O2'
_chemical_formula_weight         460.64
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-06 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                62.421(4)
_cell_angle_beta                 83.645(3)
_cell_angle_gamma                82.289(3)
_cell_formula_units_Z            4
_cell_length_a                   11.8074(4)
_cell_length_b                   16.1835(6)
_cell_length_c                   16.6250(7)
_cell_measurement_reflns_used    10294
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.2860
_cell_measurement_theta_min      6.0140
_cell_volume                     2786.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.109a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_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    -74.00 -48.00   1.00    7.50    --  -43.13 129.00 -90.00   26
  2  \w   -114.00 -67.00   1.00    7.50    --  -43.13-141.00  24.00   47
  3  \w     49.00 101.00   1.00    7.50    --   43.13-129.00-163.00   52
  4  \w     54.00  79.00   1.00    7.50    --   43.13-141.00  24.00   25
  5  \w     96.00 136.00   1.00   30.00    --  103.80 129.00 -90.00   40
  6  \w     65.00 113.00   1.00   30.00    --  103.80-129.00-163.00   48
  7  \w    106.00 131.00   1.00   30.00    --  103.80 141.00  81.00   25
  8  \w     71.00 125.00   1.00   30.00    --  103.80-141.00  24.00   54
  9  \w     37.00  62.00   1.00   30.00    --  103.80-141.00  24.00   25
 10  \w    -66.00 -41.00   1.00    7.50    --  -43.13 141.00  81.00   25
 11  \w    -66.00  30.00   1.00    7.50    --  -43.13  37.00  30.00   96
 12  \w   -117.00 -19.00   1.00    7.50    --  -43.13 -37.00  30.00   98
 13  \w     20.00 118.00   1.00    7.50    --   43.13  37.00 -90.00   98
 14  \w    -10.00  15.00   1.00    7.50    --   43.13 -77.00  90.00   25
 15  \w     41.00 104.00   1.00   30.00    --  103.80-111.00-120.00   63
 16  \w    152.00 177.00   1.00   30.00    --  103.80  30.00 -90.00   25
 17  \w    107.00 171.00   1.00   30.00    --  103.80 111.00 150.00   64
 18  \w     83.00 138.00   1.00   30.00    --  103.80  30.00 -90.00   55
 19  \w     28.00 112.00   1.00   30.00    --  103.80 -30.00-120.00   84
 20  \w     40.00 121.00   1.00   30.00    --  103.80 -30.00  30.00   81
 21  \w     39.00 106.00   1.00   30.00    --  103.80-111.00  90.00   67
 22  \w     35.00  60.00   1.00   30.00    --  103.80 -77.00   0.00   25
 23  \w    103.00 132.00   1.00   30.00    --  103.80 -77.00   0.00   29
 24  \w     63.00 112.00   1.00   30.00    --  103.80 -45.00-180.00   49
 25  \w    106.00 166.00   1.00   30.00    --  103.80 111.00 -60.00   60
 26  \w     78.00 105.00   1.00   30.00    --  103.80-111.00   0.00   27
 27  \w    105.00 178.00   1.00   30.00    --  103.80 111.00  30.00   73
 28  \w     85.00 176.00   1.00   30.00    --  103.80  45.00-150.00   91
;
_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      -0.0462452000
_diffrn_orient_matrix_UB_12      0.0435493000
_diffrn_orient_matrix_UB_13      0.0636352000
_diffrn_orient_matrix_UB_21      0.0197171000
_diffrn_orient_matrix_UB_22      -0.0964071000
_diffrn_orient_matrix_UB_23      0.0830296000
_diffrn_orient_matrix_UB_31      0.1219075000
_diffrn_orient_matrix_UB_32      0.0211270000
_diffrn_orient_matrix_UB_33      0.0044487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11529
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         3.003
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.109a (Rigaku Oxford Diffraction, 2021)
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 pale colourless'
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     695
_refine_ls_number_reflns         11529
_refine_ls_number_restraints     708
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0998P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7996
_reflns_number_total             11529
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 4.2587\% 
around [0.02 0.84 0.54] (reciprocal) or [-0.17 0.96 0.22] (direct)
;
_cod_data_source_file            d1cc05161j2.cif
_cod_data_source_block           wf446meoh
_cod_depositor_comments
'Adding full bibliography for 7129122--7129133.cif.'
_cod_database_code               7129131
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C30 H40 N2 O2'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.904
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.611(2)
 0.389(2)
2. 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
3. Restrained distances
 C55-C54 \\sim C56-C54 \\sim C57-C54 \\sim C58-C54
 with sigma of 0.02
 C55-C57 \\sim C56-C58
 with sigma of 0.02
 C26-C27 \\sim C28-C29
 with sigma of 0.02
 C26-C25 \\sim C28-C25 \\sim C27-C25 \\sim C29-C25
 with sigma of 0.02
 C60-C59 \\sim C62-C59 \\sim C61-C59 \\sim C63-C59
 with sigma of 0.02
 C60-C61 \\sim C62-C63
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C54 \\sim C55 \\sim C56 \\sim C57 \\sim C58: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C59 \\sim C60 \\sim C61 \\sim C62 \\sim C63: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H54A)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(H55C)=Sof(C57)=Sof(H57A)=Sof(H57B)=
 Sof(H57C)=1-FVAR(1)
 Sof(H54)=Sof(C56)=Sof(H56A)=Sof(H56B)=Sof(H56C)=Sof(C58)=Sof(H58A)=Sof(H58B)=
 Sof(H58C)=FVAR(1)
 Sof(H25A)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 Sof(H29C)=1-FVAR(2)
 Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=
 Sof(H27C)=FVAR(2)
 Sof(H59A)=Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H62C)=Sof(C63)=Sof(H63A)=Sof(H63B)=
 Sof(H63C)=1-FVAR(3)
 Sof(H59)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(H60C)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(H61C)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25), C25(H25A), C42(H42), C45(H45),
 C54(H54), C54(H54A), C59(H59), C59(H59A)
7.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C30(H30), C34(H34), C35(H35), C38(H38), C39(H39), C40(H40), C50(H50), C51(H51),
  C52(H52), C64(H64)
7.c 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(H24C,H24A,H24B), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C),
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,H47B,
 H47C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C58(H58A,
 H58B,H58C), C60(H60A,H60B,H60C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C),
 C63(H63A,H63B,H63C), C66(H66A,H66B,H66C)
;
_shelx_res_checksum              73766
_shelx_hkl_checksum              44621
_olex2_date_sample_data_collection 2021-05-11
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.724
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2