Hypervalent Iodine(III) Compounds as Biaxial Halogen Bond Donors.
Heinen, Flemming; Engelage, Elric; Cramer, Christopher J.; Huber, Stefan M.; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.9b13309

data_4134828
_publ_section_title
;
 Hypervalent Iodine(III) Compounds as Biaxial Halogen Bond Donors.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13309
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic        o-phenylene-bis(N,N-dimethylpropiolamide)
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-10-17 deposited with the CCDC.	2019-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.090(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4757(2)
_cell_length_b                   18.5170(4)
_cell_length_c                   8.3509(2)
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      66.5
_cell_measurement_theta_min      4.8
_cell_volume                     1427.19(6)
_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_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -90.00 -57.00   0.50    0.13    --  -46.95 138.00  65.00   66
  2  \w    -82.00 -57.00   0.50    0.54    --  -86.25 138.00  65.00   50
  3  \w    -48.00 -14.00   0.50    0.54    --  -86.25  45.00 120.00   68
  4  \w    -45.00 -19.00   0.50    0.54    --  -86.25  45.00  60.00   52
  5  \w    -48.00 -23.00   0.50    0.54    --  -86.25  45.00  90.00   50
  6  \w    -40.00  13.00   0.50    0.13    --  -46.95  38.00 -30.00  106
  7  \w    -10.00  28.00   0.50    0.13    --  -46.95  19.00 -90.00   76
  8  \w    -17.00  28.00   0.50    0.13    --  -46.95  19.00-180.00   90
  9  \w     49.00  74.00   0.50    0.13    --   46.95-138.00   3.00   50
 10  \w     45.00  98.00   0.50    0.54    --  106.49-138.00   3.00  106
 11  \w     76.00 125.00   0.50    0.54    --  106.49-143.00  17.24   98
 12  \w     62.00  95.00   0.50    0.54    --  106.49 -94.00  30.00   66
 13  \w     35.00  73.00   0.50    0.54    --  106.49 -61.00 150.00   76
 14  \w     39.00 115.00   0.50    0.54    --  106.49-131.00 179.00  152
 15  \w     44.00  69.00   0.50    0.13    --   46.95-131.00 179.00   50
 16  \w     35.00  78.00   0.50    0.54    --  106.49 -94.00   0.00   86
 17  \w     35.00  61.00   0.50    0.54    --  106.49 -61.00-120.00   52
 18  \w     65.00 105.00   0.50    0.54    --  106.49 -94.00-180.00   80
 19  \w     38.00  72.00   0.50    0.54    --  106.49 -61.00-180.00   68
 20  \w     97.00 124.00   0.50    0.54    --  106.49  45.00-120.00   54
 21  \w    141.00 177.00   0.50    0.54    --  106.49  45.00-120.00   72
 22  \w    106.00 132.00   0.50    0.54    --  106.49 131.00-110.00   52
 23  \w     95.00 163.00   0.50    0.54    --  106.49  45.00   0.00  136
 24  \w    145.00 171.00   0.50    0.54    --  106.49  30.00  90.00   52
 25  \w    107.00 132.00   0.50    0.54    --  106.49 138.00  65.00   50
 26  \w     98.00 134.00   0.50    0.54    --  106.49  30.00  90.00   72
 27  \w   -112.00 -87.00   0.50    0.13    --  -46.95-131.00 179.00   50
 28  \w   -109.00 -66.00   0.50    0.13    --  -46.95-138.00   3.00   86
 29  \w   -123.00 -98.00   0.50    0.54    --  -86.25-131.00 179.00   50
;
_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      0.0446453000
_diffrn_orient_matrix_UB_12      0.0683274000
_diffrn_orient_matrix_UB_13      -0.0809105000
_diffrn_orient_matrix_UB_21      -0.0714014000
_diffrn_orient_matrix_UB_22      0.0473446000
_diffrn_orient_matrix_UB_23      0.1115231000
_diffrn_orient_matrix_UB_31      0.1442404000
_diffrn_orient_matrix_UB_32      0.0022863000
_diffrn_orient_matrix_UB_33      0.1297029000
_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  0.0303
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.478
_diffrn_reflns_theta_max         66.478
_diffrn_reflns_theta_min         4.776
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79549
_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            yellow
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, cyclopentane'
_exptl_crystal_size_max          0.277
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0583P)^2^+0.3460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2158
_reflns_number_total             2508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b13309_si_003.cif
_cod_data_source_block           FH-oDiamid
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4134828
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.758
_oxdiff_exptl_absorpt_empirical_full_max 1.399
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              36030
_shelx_hkl_checksum              53775