Directing group assisted meta-hydroxylation by C–H activation
Maji, Arun; Bhaskararao, Bangaru; Singha, Santanu; Sunoj, Raghavan B.; Maiti, Debabrata; Chem. Sci. 7 (2016) 3147–; doi:10.1039/C5SC04060D

data_1542308
_publ_section_title
;
 Directing group assisted meta-hydroxylation by C--H activation
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3147
_journal_paper_doi               10.1039/C5SC04060D
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C14 H10 Br N O4 S'
_chemical_formula_sum            'C14 H10 Br N O4 S'
_chemical_formula_weight         368.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-05-14
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_audit_update_record
;
2015-08-07 deposited with the CCDC.
2016-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                99.760(5)
_cell_angle_beta                 96.941(4)
_cell_angle_gamma                90.080(5)
_cell_formula_units_Z            2
_cell_length_a                   7.608(2)
_cell_length_b                   9.473(3)
_cell_length_c                   9.930(3)
_cell_measurement_temperature    100(2)
_cell_volume                     700.0(4)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10906
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.208
_exptl_absorpt_coefficient_mu    3.100
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0492P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2246
_reflns_number_total             2461
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc04060d2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1542308--1542310.cif.'
_cod_database_code               1542308
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), C20(H20), C21(H21)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6)
;
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.280
_shelx_res_checksum              17762
_shelxl_version_number           2012-9