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_7125293
_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         'C25 H26 N2 O6 S'
_chemical_formula_sum            'C25 H26 N2 O6 S'
_chemical_formula_weight         482.54
_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             2016-08-09
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-08-09 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_cell_angle_alpha                108.688(7)
_cell_angle_beta                 105.715(8)
_cell_angle_gamma                98.948(9)
_cell_formula_units_Z            2
_cell_length_a                   8.3702(10)
_cell_length_b                   12.3731(11)
_cell_length_c                   13.2427(8)
_cell_measurement_reflns_used    4831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0570
_cell_measurement_theta_min      1.9840
_cell_volume                     1205.6(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.999
_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  25.00   0.50    8.00    --  -20.00   0.00 108.00  270
  2  \w   -110.00  19.00   0.50    8.00    --  -20.00 -72.00 108.00  258
  3  \w    -74.50  19.00   0.50    8.00    --  -20.00 -72.00-108.00  187
  4  \w    -71.00 -11.00   0.50    8.00    --  -20.00 -72.00  36.00  120
  5  \w    -39.00  -9.00   0.50    8.00    --  -20.00 -72.00-180.00   60
  6  \w    -59.00  70.00   0.50    8.00    --  -20.00  72.00-108.00  258
  7  \w    -59.00  60.50   0.50    8.00    --  -20.00  72.00-180.00  239
  8  \w    -78.00 -21.00   0.50    8.00    --  -20.00 -72.00 -36.00  114
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134625000
_diffrn_orient_matrix_UB_12      0.0121871000
_diffrn_orient_matrix_UB_13      0.0582252000
_diffrn_orient_matrix_UB_21      0.0208674000
_diffrn_orient_matrix_UB_22      0.0615732000
_diffrn_orient_matrix_UB_23      0.0117361000
_diffrn_orient_matrix_UB_31      -0.0878730000
_diffrn_orient_matrix_UB_32      -0.0008455000
_diffrn_orient_matrix_UB_33      -0.0097270000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16935
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.622
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.329
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0919
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0908P)^2^+0.4343P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3104
_reflns_number_total             4231
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08302a2.cif
_cod_data_source_block           dm-am-10-cha-863_mo
_cod_original_cell_volume        1205.7(2)
_cod_database_code               7125293
_shelxl_version_number           2012-9
_reflns_odcompleteness_completeness 91.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_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:
 C2(H2A,H2B), C18(H18A,H18B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C5(H5), C4(H4), C11(H11), C9(H9), C21(H21), C13(H13),
 C22(H22), C20(H20), C23(H23)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              29444
_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 3.824
_oxdiff_exptl_absorpt_empirical_full_min 0.331