Preparation of anthranils via chemoselective oxidative radical cyclization of 3-(2-azidoaryl) substituted propargyl alcohols.
Gao, Chao; Xu, Jian; Zhu, Shuxian; Jian, Kaixia; Xuan, Qingqing; Song, Qiuling; Chemical communications (Cambridge, England) 57 (2021) 2037–2040; doi:10.1039/d0cc07919g

data_7127801
_publ_section_title
;
 Preparation of anthranils via chemoselective oxidative radical
 cyclization of 3-(2-azidoaryl) substituted propargyl alcohols.
;
_journal_issue                   16
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2037
_journal_page_last               2040
_journal_paper_doi               10.1039/d0cc07919g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C21 H13 Cl F N O'
_chemical_formula_sum            'C21 H14 Cl F N O'
_chemical_formula_weight         350.78
_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_block_doi                 10.5517/ccdc.csd.cc228zt5
_audit_creation_date             2019-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-10 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.858(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1901(8)
_cell_length_b                   13.1981(9)
_cell_length_c                   9.2973(6)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9130
_cell_measurement_theta_min      4.2720
_cell_volume                     1690.54(19)
_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, 2015)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.837
_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    -53.00  35.00   1.00    8.00    --   15.49 -19.00 -30.00   88
  2  \w    -21.00  42.00   1.00    8.00    --   15.49 -99.00 -90.00   63
  3  \w    -24.00  23.00   1.00    8.00    --  -16.12 -99.00 -60.00   47
  4  \w    -23.00  12.00   1.00    8.00    --  -16.12 -99.00 150.00   35
;
_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      0.0502599000
_diffrn_orient_matrix_UB_12      0.0084882000
_diffrn_orient_matrix_UB_13      0.0299852000
_diffrn_orient_matrix_UB_21      -0.0095643000
_diffrn_orient_matrix_UB_22      0.0518686000
_diffrn_orient_matrix_UB_23      0.0099539000
_diffrn_orient_matrix_UB_31      -0.0060519000
_diffrn_orient_matrix_UB_32      -0.0108116000
_diffrn_orient_matrix_UB_33      0.0720508000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8247
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.347
_diffrn_reflns_theta_min         3.356
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24449
_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    1.378
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0549
_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          0.1406
_refine_ls_wR_factor_ref         0.1912
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2057
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07919g2.cif
_cod_data_source_block           exp_6757
_cod_depositor_comments          'Adding full bibliography for 7127801.cif.'
_cod_database_code               7127801
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P)
;
_shelx_res_checksum              93960
_olex2_date_sample_data_collection 2019-05-10
_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 7.572
_oxdiff_exptl_absorpt_empirical_full_min 0.531