[3+1+1] type cyclization of ClCF<sub>2</sub>COONa for the assembly of imidazoles and tetrazoles via in situ generated isocyanides.
Wang, Ya; Zhou, Yao; Song, Qiuling; Chemical communications (Cambridge, England) 56 (2020) 6106–6109; doi:10.1039/d0cc01919d

data_7126410
_publ_section_title
;
 [3+1+1] type cyclization of ClCF<sub>2</sub>COONa for the assembly of
 imidazoles and tetrazoles via in situ generated isocyanides.
;
_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6106
_journal_page_last               6109
_journal_paper_doi               10.1039/d0cc01919d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C13 H14 N2 O2'
_chemical_formula_sum            'C13 H14 N2 O2'
_chemical_formula_weight         230.26
_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     direct
_audit_creation_date             2019-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_audit_update_record
;
2019-05-21 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.85(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
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_cell_length_b                   7.3514(16)
_cell_length_c                   20.934(4)
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8300
_cell_measurement_theta_min      3.9950
_cell_volume                     2509.0(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -32.00  51.00   1.00    7.50    --  -16.28  38.00  60.00   83
  2  \w    -14.00  31.00   1.00    7.50    --   15.49 -99.00 -30.00   45
  3  \w    -22.00  21.00   1.00    7.50    --  -16.28 -99.00  60.00   43
  4  \w    -23.00  23.00   1.00    7.50    --  -16.28 -99.00-150.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418124000
_diffrn_orient_matrix_UB_12      -0.0185763000
_diffrn_orient_matrix_UB_13      -0.0141698000
_diffrn_orient_matrix_UB_21      -0.0120342000
_diffrn_orient_matrix_UB_22      0.0638675000
_diffrn_orient_matrix_UB_23      0.0215082000
_diffrn_orient_matrix_UB_31      0.0000101000
_diffrn_orient_matrix_UB_32      0.0701657000
_diffrn_orient_matrix_UB_33      -0.0231996000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4649
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.481
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2199
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0487
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1614
_reflns_number_total             2199
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc01919d2.cif
_cod_data_source_block           exp_6811
_cod_depositor_comments
'Adding full bibliography for 7126410--7126412.cif.'
_cod_original_cell_volume        2509.1(10)
_cod_database_code               7126410
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Secondary CH2 refined with riding coordinates:
 C00F(H00C,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E)
2.c Idealised Me refined as rotating group:
 C00G(H00G,H00H,H00I), C00H(H00J,H00K,H00L)
;
_shelx_res_checksum              43060
_shelx_shelxl_version_number     2014/7
_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.391