An Intramolecular C(sp3)−H Imination using PhI-mCPBA
Bose, Anima; Maiti, Saikat; Sau, Sudip; Mal, Prasenjit; Chemical Communications  (2019) –; doi:10.1039/C8CC09100E

data_7122887
_publ_section_title
;
 An Intramolecular C(sp3)&#x2212;H Imination using PhI-mCPBA
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09100E
_journal_year                    2019
_chemical_formula_moiety         'C23 H22 N2'
_chemical_formula_sum            'C23 H22 N2'
_chemical_formula_weight         326.42
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-09-13 deposited with the CCDC.
2019-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                106.328(2)
_cell_angle_beta                 109.830(2)
_cell_angle_gamma                107.983(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3816(2)
_cell_length_b                   10.7214(2)
_cell_length_c                   11.0369(2)
_cell_measurement_reflns_used    8498
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.4680
_cell_measurement_theta_min      4.6880
_cell_volume                     896.17(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.951
_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   -103.00 -13.00   0.50    0.20    --  -38.50 146.00 -73.00  180
  2  \w    -89.00  -2.00   0.50    0.20    --  -38.50 125.00 120.00  174
  3  \w     24.00 100.00   0.50    0.20    --   49.31-125.00  42.00  152
  4  \w     35.00 114.00   0.50    0.20    --   49.31-146.00-124.00  158
  5  \w     42.00 118.00   0.50    1.05    --  106.38-125.00  42.00  152
  6  \w     43.00 133.00   0.50    1.05    --  106.38-146.00-124.00  180
  7  \w     94.00 171.00   0.50    1.05    --  106.38 125.00 120.00  154
  8  \w    -44.00  31.00   0.50    0.20    --  -38.50  19.00-180.00  150
  9  \w    -42.00  28.00   0.50    0.20    --  -38.50  37.00  60.00  140
 10  \w   -105.00 -35.00   0.50    0.20    --  -38.50 -37.00-150.00  140
 11  \w     26.00 114.00   0.50    0.20    --   49.31  77.00  90.00  176
 12  \w     46.00 116.00   0.50    0.20    --   49.31  37.00-180.00  140
 13  \w     44.00 120.00   0.50    1.05    --  106.38 -61.00-120.00  152
 14  \w    102.00 171.00   0.50    1.05    --  106.38  45.00-180.00  138
 15  \w     42.00 111.00   0.50    1.05    --  106.38 -45.00   0.00  138
 16  \w     44.00 120.00   0.50    1.05    --  106.38 -61.00 150.00  152
 17  \w    102.00 171.00   0.50    1.05    --  106.38  45.00-150.00  138
 18  \w     38.00 110.00   0.50    1.05    --  106.38 -30.00  60.00  144
 19  \w     42.00 118.00   0.50    1.05    --  106.38-125.00   0.00  152
 20  \w    103.00 175.00   0.50    1.05    --  106.38  30.00  90.00  144
 21  \w    102.00 171.00   0.50    1.05    --  106.38  45.00 -60.00  138
 22  \w     38.00 110.00   0.50    1.05    --  106.38 -94.00  30.00  144
 23  \w     44.00 120.00   0.50    1.05    --  106.38 -61.00  30.00  152
 24  \w     42.00 111.00   0.50    1.05    --  106.38 -45.00 150.00  138
 25  \w     42.00 118.00   0.50    1.05    --  106.38-125.00-120.00  152
 26  \w     38.00 110.00   0.50    1.05    --  106.38 -30.00 -90.00  144
 27  \w     42.00 130.00   0.50    1.05    --  106.38 -77.00  30.00  176
 28  \w     42.00 111.00   0.50    1.05    --  106.38 -45.00-180.00  138
 29  \w    102.00 171.00   0.50    1.05    --  106.38  45.00 -90.00  138
 30  \w    102.00 171.00   0.50    1.05    --  106.38  45.00  60.00  138
 31  \w     82.00 170.00   0.50    1.05    --  106.38 146.00 -73.00  176
 32  \w     26.00  78.00   0.50    0.20    --   49.31  77.00   0.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1675416000
_diffrn_orient_matrix_UB_12      0.0111704000
_diffrn_orient_matrix_UB_13      -0.0319088000
_diffrn_orient_matrix_UB_21      -0.0669344000
_diffrn_orient_matrix_UB_22      -0.0892850000
_diffrn_orient_matrix_UB_23      -0.1606417000
_diffrn_orient_matrix_UB_31      -0.0745488000
_diffrn_orient_matrix_UB_32      -0.1412097000
_diffrn_orient_matrix_UB_33      0.0149457000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1107
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12116
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.653
_diffrn_reflns_theta_min         4.721
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.1000
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2774
_refine_ls_wR_factor_ref         0.2917
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2985
_reflns_number_total             3623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09100e2.cif
_cod_data_source_block           ab-4-939l
_cod_original_cell_volume        896.17(3)
_cod_database_code               7122887
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C23H21BrN2O3
_diffrn_oxdiff_ac3_digest_frames
;
01fabf9bc220838e1f6151f0d374481fa0000500d6d
;
_diffrn_oxdiff_ac3_digest_hkl
;
01f6aae4b2d096736c4d3a8b6822ec3e652ed0
;
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C23(H23), C5(H5), C7(H7), C11(H11), C6(H6), C22(H22),
 C19(H19), C21(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              50454
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 4.942
_oxdiff_exptl_absorpt_empirical_full_min 0.177