On the dual reactivity of a Janus-type mesoionic dipole: experiments and theoretical validation.
de la Concepción, Juan García; Ávalos, Martín; Cintas, Pedro; Jiménez, José L; Light, Mark E.; Organic & biomolecular chemistry 16 (2018) 4778–4783; doi:10.1039/c8ob01195h

data_7156275
_publ_section_title
;
 On the dual reactivity of a Janus-type mesoionic dipole: experiments and
 theoretical validation.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4778
_journal_page_last               4783
_journal_paper_doi               10.1039/c8ob01195h
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H27 N3 O4 S'
_chemical_formula_sum            'C31 H27 N3 O4 S'
_chemical_formula_weight         537.61
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2018-05-09 deposited with the CCDC.
2018-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8735(3)
_cell_length_b                   18.6709(4)
_cell_length_c                   11.8780(3)
_cell_measurement_reflns_used    22301
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8740
_cell_measurement_theta_min      2.0700
_cell_volume                     2633.22(11)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -112.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000    0.0000 180

  2 omega  -58.00   36.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   54.0000  -30.0000 94

  3 omega   -7.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000   90.0000 11

  4 omega  -61.00   68.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000 -180.0000 129

  5 omega  -58.00  -23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   54.0000  -60.0000 35
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      0.0250080000
_diffrn_orient_matrix_UB_12      -0.0131011000
_diffrn_orient_matrix_UB_13      -0.0501664000
_diffrn_orient_matrix_UB_21      -0.0394245000
_diffrn_orient_matrix_UB_22      -0.0285087000
_diffrn_orient_matrix_UB_23      -0.0012095000
_diffrn_orient_matrix_UB_31      -0.0372428000
_diffrn_orient_matrix_UB_32      0.0214189000
_diffrn_orient_matrix_UB_33      -0.0324024000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27414
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         3.263
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2908 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6753
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0390P)^2^+0.5115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0723
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6471
_reflns_number_total             6753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01195h2.cif
_cod_data_source_block           2015acc0012_k_100k
_cod_depositor_comments
'Adding full bibliography for 7156274--7156275.cif.'
_cod_original_cell_volume        2633.21(10)
_cod_database_code               7156275
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 96.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.95
_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 Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              98292
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id SNFD
_olex2_submission_special_instructions 'No special instructions were received'