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_7129127
_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         'C23 H24 N2 O'
_chemical_formula_sum            'C23 H24 N2 O'
_chemical_formula_weight         344.44
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.7900(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.28771(11)
_cell_length_b                   13.5951(2)
_cell_length_c                   15.3562(3)
_cell_measurement_reflns_used    14883
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      71.6300
_cell_measurement_theta_min      4.3300
_cell_volume                     1938.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (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 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_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     13.00  86.00   0.50    1.00    --   59.26-117.00-103.00  146
  2  \w     72.00  97.00   0.50    1.00    --   59.26-164.00 107.00   50
  3  \w    -82.00 -54.00   0.50    1.00    --  -62.07-164.00 107.00   56
  4  \w    -96.00 -71.00   0.50    1.00    --  -62.07 164.00 132.00   50
  5  \w    -56.00 -16.00   0.50    1.00    --  -62.07 117.00 -16.00   80
  6  \w     51.00  96.00   0.50    1.00    --   73.26-117.00-103.00   90
  7  \w     57.00  82.00   0.50    1.00    --   73.26 164.00 132.00   50
  8  \w   -104.00 -79.00   0.50    2.00    --  -74.55-164.00 107.00   50
  9  \w   -105.00 -80.00   0.50    2.00    --  -75.95-164.00 107.00   50
 10  \w   -106.00 -81.00   0.50    2.00    --  -75.95 164.00 132.00   50
 11  \w    -91.00 -66.00   0.50    2.00    --  -75.95 117.00 -16.00   50
 12  \w     62.00  88.00   0.50    2.00    --   79.85-117.00-103.00   52
 13  \w     61.00  86.00   0.50    2.00    --   79.85-164.00 107.00   50
 14  \w     61.00  86.00   0.50    2.00    --   79.85 164.00 132.00   50
 15  \w     48.00  74.00   0.50    1.00    --   38.00  64.00-171.44   52
 16  \w     44.00  77.00   0.50    1.00    --   38.00  70.00   1.91   66
 17  \w     61.00  94.00   0.50    1.00    --   54.00  68.00 -82.41   66
 18  \w     70.00  99.00   0.50    1.00    --   58.00  69.00-177.03   58
 19  \w   -110.00 -84.00   0.50    1.00    --  -66.00 -57.00 -58.55   52
 20  \w     64.00 115.00   0.50    1.00    --   66.26  28.00 110.00  102
 21  \w     35.00  79.00   0.50    1.00    --   73.26 -95.00 120.00   88
 22  \w   -108.00 -78.00   0.50    1.00    --  -74.00 -74.00  -3.69   60
 23  \w   -127.00 -96.00   0.50    2.00    --  -79.25 -40.00-122.55   62
 24  \w   -119.00 -94.00   0.50    2.00    --  -79.25 -54.00 -28.64   50
 25  \w   -116.00 -91.00   0.50    2.00    --  -79.25 -79.00-170.66   50
 26  \w   -117.00 -84.00   0.50    2.00    --  -79.25 -70.00 142.90   66
 27  \w   -116.00 -81.00   0.50    2.00    --  -79.25 -85.00 -59.10   70
 28  \w   -104.00 -50.00   0.50    2.00    --  -79.25 114.00 -41.58  108
 29  \w     50.00  86.00   0.50    2.00    --   79.85 -95.00   0.00   72
 30  \w     48.00  82.00   0.50    2.00    --   79.85  15.00 -60.00   68
 31  \w     42.00  84.00   0.50    2.00    --   79.85 -95.00 -90.00   84
 32  \w     44.00  81.00   0.50    2.00    --   79.85 -95.00 120.00   74
 33  \w     77.00 103.00   0.50    2.00    --   79.85-111.00 150.00   52
 34  \w     37.00  63.00   0.50    2.00    --   79.85-111.00 -60.00   52
 35  \w     98.00 129.00   0.50    2.00    --   79.85  30.00 -30.00   62
 36  \w     41.00  74.00   0.50    2.00    --   79.85 -95.00  30.00   66
 37  \w     52.00 100.00   0.50    2.00    --   79.85 178.00-150.00   96
 38  \w     61.00 120.00   0.50    2.00    --   79.85 178.00 150.00  118
 39  \w     75.00 101.00   0.50    2.00    --   79.85-111.00 -90.00   52
 40  \w     46.00  97.00   0.50    2.00    --   79.85   0.00-120.00  102
 41  \w     56.00 103.00   0.50    2.00    --   79.85-111.00-150.00   94
 42  \w     84.00 128.00   0.50    2.00    --   79.85  30.00  30.00   88
 43  \w     45.00  70.00   0.50    2.00    --   79.85 -95.00 -60.00   50
 44  \w     35.00  68.00   0.50    2.00    --   79.85-111.00-180.00   66
 45  \w     45.00  79.00   0.50    2.00    --   79.85 -95.00 -30.00   68
 46  \w     73.00  99.00   0.50    2.00    --   79.85-111.00   0.00   52
 47  \w     84.00 113.00   0.50    2.00    --   79.85  30.00  90.00   58
 48  \w     78.00 103.00   0.50    2.00    --   79.85-111.00 120.00   50
 49  \w     37.00  63.00   0.50    2.00    --   79.85-111.00 120.00   52
 50  \w    100.00 127.00   0.50    2.00    --   79.85  30.00-150.00   54
 51  \w     77.00 103.00   0.50    2.00    --   79.85-111.00  30.00   52
 52  \w     47.00  78.00   0.50    2.00    --   79.85 -95.00-150.00   62
 53  \w     35.00  70.00   0.50    2.00    --   79.85-111.00  30.00   70
 54  \w     77.00 103.00   0.50    2.00    --   79.85-111.00-180.00   52
 55  \w     44.00  69.00   0.50    2.00    --   79.85 -95.00 150.00   50
 56  \w     54.00  97.00   0.50    2.00    --   79.85   0.00 -60.00   86
 57  \w     50.00  76.00   0.50    2.00    --   79.85-111.00-120.00   52
 58  \w     70.00  96.00   0.50    2.00    --   79.85-111.00  60.00   52
 59  \w     44.00  74.00   0.50    2.00    --   79.85 -95.00-180.00   60
 60  \w     66.00  96.00   0.50    2.00    --   79.85 178.00  90.00   60
 61  \w     76.00 112.00   0.50    2.00    --   79.85  15.00  90.00   72
 62  \w     53.00 116.00   0.50    2.00    --   79.85 178.00  60.00  126
 63  \w     83.00 108.00   0.50    2.00    --   79.85  30.00-120.00   50
 64  \w     40.00 119.00   0.50    2.00    --   83.00-135.00 -65.07  158
 65  \w     71.00 118.00   0.50    2.00    --   83.00   7.00 -21.97   94
 66  \w     51.00 109.00   0.50    2.00    --   83.00-115.00 -28.68  116
 67  \w     62.00 118.00   0.50    2.00    --   83.00 152.00-153.53  112
 68  \w     86.00 120.00   0.50    2.00    --   83.00  73.00 116.10   68
 69  \w     41.00 122.00   0.50    2.00    --   83.00-140.00 137.65  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0548052000
_diffrn_orient_matrix_UB_12      0.0913008000
_diffrn_orient_matrix_UB_13      -0.0498103000
_diffrn_orient_matrix_UB_21      -0.0546432000
_diffrn_orient_matrix_UB_22      0.0442433000
_diffrn_orient_matrix_UB_23      0.0858419000
_diffrn_orient_matrix_UB_31      0.1467060000
_diffrn_orient_matrix_UB_32      0.0504419000
_diffrn_orient_matrix_UB_33      0.0148729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            40503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.060
_diffrn_reflns_theta_min         4.344
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0385
_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^)+(0.0564P)^2^+0.3077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3238
_reflns_number_total             3989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05161j2.cif
_cod_data_source_block           wf458
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7129122--7129133.cif.
;
_cod_database_code               7129127
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C23 H24 N2 O'
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
2. Others
 Sof(H24A)=Sof(H24B)=Sof(H24C)=1-FVAR(1)
 Sof(H24D)=Sof(H24E)=Sof(H24F)=FVAR(1)
 Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(2)
 Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(2)
 Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(3)
 Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(3)
 Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(4)
 Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(4)
 Sof(H15D)=Sof(H15E)=Sof(H15F)=1-FVAR(5)
 Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(5)
 Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(6)
 Sof(H16B)=Sof(H16A)=Sof(H16C)=FVAR(6)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C12(H12), C19(H19), C21(H21)
3.b Disordered Me refined as rotating group:
 C14(H14A,H14B,H14C,H14D,H14E,H14F), C15(H15A,H15B,H15C,H15D,H15E,H15F),
 C16(H16B,H16A,H16C,H16D,H16E,H16F), C23(H23A,H23B,H23C,H23D,H23E,H23F),
 C24(H24A,H24B,H24C,H24D,H24E,H24F), C25(H25A,H25B,H25C,H25D,H25E,H25F)
;
_shelx_res_checksum              23546
_shelx_hkl_checksum              24538
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.806