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_7129123
_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         'C58 H72 N4 O2'
_chemical_formula_sum            'C58 H72 N4 O2'
_chemical_formula_weight         857.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-02
_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                90
_cell_angle_beta                 99.9129(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7877(2)
_cell_length_b                   12.66021(12)
_cell_length_c                   37.7430(4)
_cell_measurement_reflns_used    19442
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.8640
_cell_measurement_theta_min      3.6570
_cell_volume                     10255.48(18)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (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                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -63.00  33.00   1.00    1.00    --  -41.04  29.00  50.00   96
  2  \w   -118.00 -28.00   1.00    1.00    --  -41.04 -29.00-110.00   90
  3  \w     87.00 117.00   1.00    1.00    --   41.04  29.00  50.00   30
  4  \w     41.00  89.00   1.00    1.00    --  112.00 -29.00-110.00   48
  5  \w     92.00 122.00   1.00    1.00    --  112.00 -29.00-110.00   30
  6  \w    114.00 178.00   1.00    1.00    --  112.00  29.00  50.00   64
  7  \w    -58.00  -9.00   1.00    1.00    --  -41.04 125.00  60.00   49
  8  \w    -20.00  70.00   1.00    1.00    --   41.04 -77.00-180.00   90
  9  \w     56.00  96.00   1.00    1.00    --   41.04-125.00 -90.00   40
 10  \w     -8.00  17.00   1.00    1.00    --   41.04 -29.00-110.00   25
 11  \w     30.00  85.00   1.00    1.00    --   41.04-125.00  90.00   55
 12  \w     29.00  74.00   1.00    1.00    --  112.00 -94.00-120.00   45
 13  \w     90.00 124.00   1.00    1.00    --  112.00  45.00 -90.00   34
 14  \w     41.00 141.00   1.00    1.00    --  112.00 -61.00   0.00  100
 15  \w    137.00 163.00   1.00    1.00    --  112.00 111.00-180.00   26
 16  \w     62.00 138.00   1.00    1.00    --  112.00 178.00-120.00   76
 17  \w    142.00 178.00   1.00    1.00    --  112.00  30.00 150.00   36
 18  \w    127.00 171.00   1.00    1.00    --  112.00  45.00  90.00   44
 19  \w    105.00 147.00   1.00    1.00    --  112.00 111.00 -30.00   42
 20  \w     48.00 141.00   1.00    1.00    --  112.00 -61.00 -90.00   93
 21  \w     70.00 106.00   1.00    1.00    --  112.00 -94.00 -60.00   36
 22  \w     46.00  71.00   1.00    1.00    --  112.00-111.00  60.00   25
 23  \w     36.00  73.00   1.00    1.00    --  112.00 -94.00-150.00   37
 24  \w     84.00 109.00   1.00    1.00    --  112.00-111.00 120.00   25
 25  \w     76.00 109.00   1.00    1.00    --  112.00-111.00  60.00   33
 26  \w    104.00 130.00   1.00    1.00    --  112.00 111.00-180.00   26
 27  \w     81.00 109.00   1.00    1.00    --  112.00-111.00-150.00   28
 28  \w     85.00 129.00   1.00    1.00    --  112.00  30.00 150.00   44
 29  \w    150.00 178.00   1.00    1.00    --  112.00  15.00 120.00   28
 30  \w     45.00 149.00   1.00    1.00    --  112.00 -15.00  90.00  104
 31  \w     59.00 109.00   1.00    1.00    --  112.00-111.00   0.00   50
 32  \w     73.00 109.00   1.00    1.00    --  112.00-111.00 150.00   36
 33  \w     66.00 109.00   1.00    1.00    --  112.00-111.00 -90.00   43
 34  \w     82.00 107.00   1.00    1.00    --  112.00-111.00  90.00   25
 35  \w     59.00 129.00   1.00    1.00    --  112.00  15.00 120.00   70
 36  \w     36.00 102.00   1.00    1.00    --  112.00-111.00 -60.00   66
 37  \w     49.00  75.00   1.00    1.00    --  112.00-111.00-150.00   26
 38  \w     40.00  65.00   1.00    1.00    --  112.00-111.00 120.00   25
 39  \w     76.00 107.00   1.00    1.00    --  112.00-111.00-120.00   31
 40  \w     59.00 107.00   1.00    1.00    --  112.00-111.00  30.00   48
 41  \w     37.00  63.00   1.00    1.00    --  112.00 -94.00 -60.00   26
 42  \w     31.00  56.00   1.00    1.00    --  112.00 -94.00  90.00   25
 43  \w     48.00  84.00   1.00    1.00    --  112.00 -94.00-180.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0708032000
_diffrn_orient_matrix_UB_12      0.0065231000
_diffrn_orient_matrix_UB_13      0.0133844000
_diffrn_orient_matrix_UB_21      0.0061543000
_diffrn_orient_matrix_UB_22      -0.1185337000
_diffrn_orient_matrix_UB_23      -0.0079311000
_diffrn_orient_matrix_UB_31      0.0100509000
_diffrn_orient_matrix_UB_32      0.0267282000
_diffrn_orient_matrix_UB_33      -0.0384082000
_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  0.0392
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            60758
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.063
_diffrn_reflns_theta_min         3.688
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.512
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.407
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (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 intense yellow'
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_description       prism
_exptl_crystal_F_000             3712
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.000248(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         10659
_refine_ls_number_restraints     160
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0615P)^2^+5.9839P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9079
_reflns_number_total             10659
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05161j2.cif
_cod_data_source_block           wf446hcl
_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_original_cell_volume        10255.47(18)
_cod_database_code               7129123
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C58 H72 N4 O2'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.752
_reflns_odcompleteness_completeness 99.93
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21A-C19 \\sim C21B-C19 \\sim C20A-C19 \\sim C20B-C19
 with sigma of 0.01
 C48A-C46 \\sim C48B-C46 \\sim C47A-C46 \\sim C47B-C46
 with sigma of 0.02
 C47A-C48A \\sim C47B-C48B
 with sigma of 0.02
 C59B-C60B \\sim C60A-C59A
 with sigma of 0.02
 C59B-C58B \\sim C59A-C58A \\sim C60B-C58B \\sim C60A-C58A
 with sigma of 0.01
 C58B-C54 \\sim C54-C58A
 with sigma of 0.01
 C21A-C20A \\sim C21B-C20B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C46 \\sim C47A \\sim C47B \\sim C48A \\sim C48B: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
C19 \\sim C20A \\sim C20B \\sim C21A \\sim C21B: within 2A with sigma of 0.005
and sigma for terminal atoms of 0.01 within 2A
C58A \\sim C58B \\sim C59A \\sim C59B \\sim C60A \\sim C60B: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(C58B)=Sof(H58B)=Sof(C59B)=Sof(H59D)=Sof(H59E)=Sof(H59F)=Sof(C60B)=
 Sof(H60D)=Sof(H60E)=Sof(H60F)=1-FVAR(1)
 Sof(C58A)=Sof(H58A)=Sof(C59A)=Sof(H59A)=Sof(H59B)=Sof(H59C)=Sof(C60A)=
 Sof(H60A)=Sof(H60B)=Sof(H60C)=FVAR(1)
 Sof(H46A)=Sof(C47B)=Sof(H47D)=Sof(H47E)=Sof(H47F)=Sof(C48B)=Sof(H48D)=
 Sof(H48E)=Sof(H48F)=1-FVAR(2)
 Sof(H46)=Sof(C47A)=Sof(H47A)=Sof(H47B)=Sof(H47C)=Sof(C48A)=Sof(H48A)=
 Sof(H48B)=Sof(H48C)=FVAR(2)
 Sof(H19A)=Sof(C20B)=Sof(H20D)=Sof(H20E)=Sof(H20F)=Sof(C21B)=Sof(H21D)=
 Sof(H21E)=Sof(H21F)=1-FVAR(3)
 Sof(H19)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=Sof(H21C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C19(H19A), C22(H22), C31(H31), C34(H34), C43(H43), C46(H46),
 C46(H46A), C55(H55), C58A(H58A), C58B(H58B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C27(H27),
 C28(H28), C29(H29), C39(H39), C40(H40), C41(H41), C51(H51), C52(H52), C53(H53)
5.c Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C20B(H20D,H20E,H20F), C21A(H21A,H21B,H21C), C21B(H21D,
 H21E,H21F), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C32(H32A,H32B,H32C),
 C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C44(H44A,H44B,
 H44C), C45(H45A,H45B,H45C), C47A(H47A,H47B,H47C), C47B(H47D,H47E,H47F),
 C48A(H48A,H48B,H48C), C48B(H48D,H48E,H48F), C56(H56A,H56B,H56C), C57(H57A,H57B,
 H57C), C59A(H59A,H59B,H59C), C59B(H59D,H59E,H59F), C60A(H60A,H60B,H60C),
 C60B(H60D,H60E,H60F)
;
_shelx_res_checksum              2905
_shelx_hkl_checksum              52916
_olex2_date_sample_data_collection 2021-05-06
_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 1.695
_oxdiff_exptl_absorpt_empirical_full_min 0.773