Preparation and X-ray Crystal Study of Benziodoxaborole Derivatives: New Hypervalent Iodine Heterocycles
Victor N. Nemykin; Andrey V. Maskaev; Margarita R. Geraskina; Mekhman S. Yusubov; Viktor V. Zhdankin; Inorganic Chemistry 50 (2011) 11263–11272; doi:10.1021/ic201922n

data_4326788
_publ_contact_author_address
; 
 Department of Chemistry & Biochemistry, 
 1039 University Drive,
 University of Minnesota Duluth, 
 Duluth, MN 55812, USA. 
;
_publ_contact_author_email       vnemykin@d.umn.edu
_publ_contact_author_fax         '+1 218 7267394'
_publ_contact_author_name        'Victor N. Nemykin'
_publ_contact_author_phone       '+1 218 7266729'
_publ_section_title
;
 Preparation and X-ray Crystal Study of Benziodoxaborole Derivatives: New
 Hypervalent Iodine Heterocycles
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11263
_journal_page_last               11272
_journal_paper_doi               10.1021/ic201922n
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C6 H4 B1 Cl1 F1 I1 O2'
_chemical_formula_sum            'C6 H4 B Cl F I O2'
_chemical_formula_weight         300.26
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-07-03
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                109.722(8)
_cell_angle_beta                 99.391(7)
_cell_angle_gamma                97.560(7)
_cell_formula_units_Z            4
_cell_length_a                   7.4745(4)
_cell_length_b                   10.5487(6)
_cell_length_c                   11.7411(8)
_cell_measurement_reflns_used    3861
_cell_measurement_temperature    123
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     842.22(11)
_computing_cell_refinement       'CrystalClear 2.0'
_computing_data_collection       'CrystalClear 2.0'
_computing_data_reduction        'CrystalStructure 4.0'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Rigaku RAPID II'
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.043
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22003
_diffrn_reflns_theta_full        27.481
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.026
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  4
_diffrn_standards_number         3861
_exptl_absorpt_coefficient_mu    4.086
_exptl_absorpt_correction_T_max  0.61
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.368
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.74
_refine_diff_density_min         -0.90
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9739
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0272
_refine_ls_shift/su_max          0.0006621
_refine_ls_shift/su_mean         0.0000253
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.81P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0667
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0667
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3112
_reflns_number_total             3861
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.89
_oxford_diffrn_Wilson_scale      7.53
_oxford_refine_ls_r_factor_ref   0.0341
_oxford_refine_ls_scale          0.3721(3)
_oxford_reflns_number_all        3840
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '_061810_VZ1'
_cod_data_source_file            ic201922n_si_001_2.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C6 H4 B1 Cl1 F1 I1 O2'
_cod_database_code               4326788
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE O   (   2,X'S) H   (  18,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE O   (   4,X'S) H   (   3,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
END                                                                             
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_iucr_refine_instruction_details_restraints
;
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 6) TO H(61) 
REST 0.053, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(1) 
CONT H(61) TO C ( 6) TO C(5) 
PLANAR C ( 6) C(1) C(5) H(61) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 5) TO H(51) 
REST 0.062, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(51) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
PLANAR C ( 5) C(6) C(4) H(51) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 4) TO H(41) 
REST 0.063, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(41) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
PLANAR C ( 4) C(5) C(3) H(41) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 12) TO H(121) 
REST 0.049, 0.002 = H(121,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(121) TO C ( 12) TO C(7) 
CONT H(121) TO C ( 12) TO C(11) 
PLANAR C ( 12) C(7) C(11) H(121) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 11) TO H(111) 
REST 0.059, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(12) 
CONT H(111) TO C ( 11) TO C(10) 
PLANAR C ( 11) C(12) C(10) H(111) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 10) TO H(101) 
REST 0.060, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(11) 
CONT H(101) TO C ( 10) TO C(9) 
PLANAR C ( 10) C(11) C(9) H(101) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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