Remote meta C-H bond functionalization of 2-phenethylsulphonic acid and 3-phenylpropanoic acid derivatives.
Modak, Atanu; Mondal, Anirban; Watile, Rahul; Mukherjee, Semanti; Maiti, Debabrata; Chemical communications (Cambridge, England) 52 (2016) 13916–13919; doi:10.1039/c6cc08302a

data_7125292
_publ_section_title
;
 Remote meta C-H bond functionalization of 2-phenethylsulphonic acid and
 3-phenylpropanoic acid derivatives.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13916
_journal_page_last               13919
_journal_paper_doi               10.1039/c6cc08302a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H18 Br N O5 S'
_chemical_formula_sum            'C20 H18 Br N O5 S'
_chemical_formula_weight         464.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-28 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                92.1745(19)
_cell_angle_beta                 99.8465(19)
_cell_angle_gamma                107.839(2)
_cell_formula_units_Z            2
_cell_length_a                   7.88851(18)
_cell_length_b                   8.9545(2)
_cell_length_c                   14.9033(3)
_cell_measurement_reflns_used    7103
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.1930
_cell_measurement_theta_min      2.3910
_cell_volume                     982.77(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.880
_diffrn_measured_fraction_theta_max 0.977
_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   -110.00  70.00   0.50    8.00    --  -20.00   0.00  36.00  360
  2  \w    -78.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  194
  3  \w    -71.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  180
  4  \w    -33.50  17.50   0.50    8.00    --  -20.00 -72.00 -36.00  102
  5  \w     -2.00   8.50   0.50    8.00    --  -20.00  72.00-180.00   21
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338098000
_diffrn_orient_matrix_UB_12      0.0610916000
_diffrn_orient_matrix_UB_13      -0.0157336000
_diffrn_orient_matrix_UB_21      -0.0338774000
_diffrn_orient_matrix_UB_22      -0.0424693000
_diffrn_orient_matrix_UB_23      -0.0438982000
_diffrn_orient_matrix_UB_31      -0.0835032000
_diffrn_orient_matrix_UB_32      -0.0381227000
_diffrn_orient_matrix_UB_33      0.0134403000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.880
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7447
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.401
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0322P)^2^+0.5771P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3208
_reflns_number_total             3392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08302a2.cif
_cod_data_source_block           dm-anm-3-br-ome_mo
_cod_original_cell_volume        982.76(4)
_cod_database_code               7125292
_shelxl_version_number           2012-9
_chemical_oxdiff_formula         'C20 H18 Br1 N1 O5 S1'
_reflns_odcompleteness_completeness 88.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.04
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00D), C00K(H00E,H00G), C00L(H00I,H00K)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00J),
 C00P(H00P), C00R(H00R), C00S(H00S)
2.c Idealised Me refined as rotating group:
 C00N(H00L,H00M,H00N)
;
_shelx_res_checksum              39399
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.858