A halogen-bonding-catalysed Nazarov cyclisation reaction
Dreger, Alexander; Wonner, Patrick; Engelage, Elric; Walter, Sebastian M.; Stoll, Raphael; Huber, Stefan M.; Chemical Communications  (2019) –; doi:10.1039/C9CC02816A

data_7123735
_publ_section_title
;
 A halogen-bonding-catalysed Nazarov cyclisation reaction
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02816A
_journal_year                    2019
_chemical_formula_sum            'C15 H15 F O2'
_chemical_formula_weight         246.27
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-02-21 deposited with the CCDC.    2019-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.495(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.61050(10)
_cell_length_b                   11.8833(2)
_cell_length_c                   15.8503(4)
_cell_measurement_reflns_used    2143
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      4.7
_cell_volume                     1224.28(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.29a (Rigaku OD, 2018)'
_computing_molecular_graphics
;
 Diamond 4 - Crystal and Molecular Structure Visualization
  Crystal Impact - Dr. H. Putz & Dr. K. Brandenburg GbR, 
  Kreuzherrenstr. 102, 53227 Bonn, Germany
  http://www.crystalimpact.com/diamond
 Mercury CSD 2.0 - New Features for the Visualization and Investigation of Crystal Structures
  C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, 
  L. Rodriguez-Monge, R. Taylor, J. van de Streek and P. A. Wood, 
  J. Appl. Cryst., 41, 466-470, 2008
;
_computing_publication_material
'WinGX L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
;
 shelXT  G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
 shelXle C. B. Huebschle, G. M. Sheldrick and B. Dittrich J. Appl. Cryst. (2011). 44, 1281-1284
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_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   -118.00 -34.00   0.50    0.14    --  -47.45 -15.00-141.00  168
  2  \w    -20.00  11.00   0.50    0.14    --  -47.45  15.00  28.00   62
  3  \w    -24.00   1.00   0.50    0.14    --   47.45 -15.00-141.00   50
  4  \w     61.00  87.00   0.50    0.14    --   47.45  15.00  28.00   52
  5  \w   -127.00 -72.00   0.50    0.55    --  -86.25 -15.00-141.00  110
  6  \w     98.00 174.00   0.50    0.55    --  106.49  15.00  28.00  152
  7  \w   -108.00 -73.00   0.50    0.14    --  -47.45-125.00-150.00   70
  8  \w    -85.00 -26.00   0.50    0.14    --  -47.45 125.00-180.00  118
  9  \w      9.00  43.00   0.50    0.14    --   47.45 -38.00  90.00   68
 10  \w    -64.00 -38.00   0.50    0.55    --  -86.25 125.00  60.00   52
 11  \w    -45.00 -15.00   0.50    0.55    --  -86.25  45.00-150.00   60
 12  \w    -47.00 -14.00   0.50    0.55    --  -86.25  45.00 -30.00   66
 13  \w     79.00 107.00   0.50    0.55    --  106.49-125.00 120.00   56
 14  \w     73.00 103.00   0.50    0.55    --  106.49-125.00  90.00   60
 15  \w     34.00  73.00   0.50    0.55    --  106.49-125.00 120.00   78
 16  \w     44.00  70.00   0.50    0.55    --  106.49-125.00  90.00   52
 17  \w     35.00  69.00   0.50    0.55    --  106.49 -61.00  90.00   68
 18  \w     44.00  69.00   0.50    0.55    --  106.49 -61.00-120.00   50
 19  \w     60.00  97.00   0.50    0.55    --  106.49 -94.00 120.00   74
 20  \w    103.00 167.00   0.50    0.55    --  106.49  15.00 -30.00  128
 21  \w     35.00  73.00   0.50    0.55    --  106.49 -61.00 150.00   76
 22  \w     40.00  66.00   0.50    0.55    --  106.49 -61.00  30.00   52
 23  \w     46.00  94.00   0.50    0.55    --  106.49 -94.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2210778000
_diffrn_orient_matrix_UB_12      0.0139005000
_diffrn_orient_matrix_UB_13      -0.0502412000
_diffrn_orient_matrix_UB_21      0.0769937000
_diffrn_orient_matrix_UB_22      -0.0211011000
_diffrn_orient_matrix_UB_23      -0.0847092000
_diffrn_orient_matrix_UB_31      -0.0368162000
_diffrn_orient_matrix_UB_32      -0.1271633000
_diffrn_orient_matrix_UB_33      0.0085452000
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6967
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.484
_diffrn_reflns_theta_max         66.484
_diffrn_reflns_theta_min         4.679
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.29a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CDCl3, evaporation from NMR-tube'
_exptl_crystal_size_max          0.191
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0393P)^2^+0.2876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1831
_reflns_number_total             2143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02816a2.cif
_cod_data_source_block           ad-246
_cod_database_code               7123735
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.824
_oxdiff_exptl_absorpt_empirical_full_max 1.245
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              71426
_shelx_hkl_checksum              99825