Aminium cation-radical catalysed selective hydration of (<i>E</i>)-aryl enynes.
Giel, Marie-Claire; Barrow, Andrew S.; Smedley, Christopher J.; Lewis, William; Moses, John E.; Chemical communications (Cambridge, England) 57 (2021) 6991–6994; doi:10.1039/d1cc02257a

data_7128543
_publ_section_title
;
 Aminium cation-radical catalysed selective hydration of (<i>E</i>)-aryl
 enynes.
;
_journal_issue                   57
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6991
_journal_page_last               6994
_journal_paper_doi               10.1039/d1cc02257a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H23 N O7, C H2 Cl2'
_chemical_formula_sum            'C24 H25 Cl2 N O7'
_chemical_formula_weight         510.35
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2021-01-29 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                72.5999(17)
_cell_angle_beta                 78.0024(16)
_cell_angle_gamma                89.0863(16)
_cell_formula_units_Z            2
_cell_length_a                   6.85821(12)
_cell_length_b                   12.4948(3)
_cell_length_c                   15.2391(3)
_cell_measurement_reflns_used    16827
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      76.8650
_cell_measurement_theta_min      4.0260
_cell_volume                     1217.40(5)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.969
_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      7.00  32.00   0.50    0.50    --    0.00 -19.00   0.00   50
  2  \w     34.00  80.00   0.50    0.50    --    0.00  38.00 -30.00   92
  3  \w    -20.00  21.00   0.50    0.50    --    0.00 -38.00 -30.00   82
  4  \w    -16.00  32.00   0.50    0.50    --    0.00 -19.00 -90.00   96
  5  \w    -21.00  30.00   0.50    0.50    --    0.00  38.00 -30.00  102
  6  \w    -23.00  26.00   0.50    0.50    --    0.00  38.00-150.00   98
  7  \w    -26.00   1.00   0.50    0.50    --    0.00 -19.00   0.00   54
  8  \w    -32.00  32.00   0.50    0.50    --    0.00 -19.00  90.00  128
  9  \w      1.00  33.00   0.50    0.50    --    0.00 -82.00  60.00   64
 10  \w    -30.00  32.00   0.50    0.50    --    0.00 -82.00   0.00  124
 11  \w    -33.00  20.00   0.50    0.50    --    0.00 -82.00 -60.00  106
 12  \w     76.00 128.00   0.50    0.50    --  102.40  61.00-120.00  104
 13  \w    127.00 191.00   0.50    0.50    --  102.40  45.00-150.00  128
 14  \w    155.00 190.00   0.50    0.50    --  102.40  45.00 -60.00   70
 15  \w    136.00 163.00   0.50    0.50    --  102.40  61.00-120.00   54
 16  \w    119.00 192.00   0.50    0.50    --  102.40  61.00   0.00  146
 17  \w    124.00 191.00   0.50    0.50    --  102.40  61.00 150.00  134
 18  \w    113.00 192.00   0.50    0.50    --  102.40  61.00 120.00  158
 19  \w    112.00 137.00   0.50    0.50    --  102.40  45.00-120.00   50
 20  \w    111.00 191.00   0.50    0.50    --  102.40  61.00-180.00  160
 21  \w     80.00 175.00   0.50    0.50    --  102.40  45.00 -30.00  190
 22  \w     81.00 110.00   0.50    0.50    --  102.40  45.00  30.00   58
 23  \w     76.00 105.00   0.50    0.50    --  102.40  61.00   0.00   58
 24  \w     76.00 105.00   0.50    0.50    --  102.40  61.00 -60.00   58
 25  \w     80.00 133.00   0.50    0.50    --  102.40  45.00   0.00  106
 26  \w     80.00 106.00   0.50    0.50    --  102.40  45.00-120.00   52
 27  \w     76.00 108.00   0.50    0.50    --  102.40  61.00-180.00   64
 28  \w     79.00 105.00   0.50    0.50    --  102.40  45.00 -90.00   52
 29  \w     76.00 124.00   0.50    0.50    --  102.40  61.00 -30.00   96
 30  \w     79.00 188.00   0.50    0.50    --  102.40  45.00  90.00  218
 31  \w     76.00 189.00   0.50    0.50    --  102.40  61.00  60.00  226
 32  \w     76.00 142.00   0.50    0.50    --  102.40  61.00  30.00  132
 33  \w     79.00 112.00   0.50    0.50    --  102.40  45.00-150.00   66
 34  \w     79.00 110.00   0.50    0.50    --  102.40  45.00-180.00   62
 35  \w     80.00 124.00   0.50    0.50    --  102.40  45.00 -60.00   88
 36  \w     76.00 102.00   0.50    0.50    --  102.40  61.00  90.00   52
 37  \w     79.00 137.00   0.50    0.50    --  102.40  45.00  60.00  116
 38  \w     76.00 107.00   0.50    0.50    --  102.40  61.00 120.00   62
 39  \w     76.00 121.00   0.50    0.50    --  102.40  61.00 150.00   90
 40  \w     80.00 113.00   0.50    0.50    --  102.40  45.00 120.00   66
 41  \w     80.00 107.00   0.50    0.50    --  102.40  45.00 150.00   54
 42  \w     76.00 171.00   0.50    0.50    --  102.40  61.00 -90.00  190
 43  \w     76.00 109.00   0.50    0.50    --  102.40  61.00-150.00   66
 44  \w     14.00 113.00   0.50    0.50    --  102.40 -77.00 150.00  198
 45  \w    104.00 134.00   0.50    0.50    --  102.40 -82.00  90.00   60
 46  \w     63.00 100.00   0.50    0.50    --  102.40 -82.00  30.00   74
 47  \w     66.00 136.00   0.50    0.50    --  102.40 -82.00-150.00  140
 48  \w     37.00 116.00   0.50    0.50    --  102.40 -82.00   0.00  158
 49  \w     30.00 132.00   0.50    0.50    --  102.40 -82.00 -30.00  204
 50  \w     13.00 115.00   0.50    0.50    --  102.40 -82.00 -90.00  204
 51  \w     21.00 110.00   0.50    0.50    --  102.40 -82.00 120.00  178
 52  \w     17.00  94.00   0.50    0.50    --  102.40 -82.00  90.00  154
 53  \w     20.00  59.00   0.50    0.50    --  102.40 -82.00-150.00   78
 54  \w    -76.00 -49.00   0.50    0.50    --    0.00 -19.00   0.00   54
 55  \w    -80.00 -43.00   0.50    0.50    --    0.00 -19.00  90.00   74
 56  \w    -88.00 -22.00   0.50    0.50    --    0.00 -38.00 -30.00  132
 57  \w    -87.00 -57.00   0.50    0.50    --    0.00 -19.00 -90.00   60
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0779127000
_diffrn_orient_matrix_UB_12      -0.1014293000
_diffrn_orient_matrix_UB_13      -0.0227532000
_diffrn_orient_matrix_UB_21      -0.0971640000
_diffrn_orient_matrix_UB_22      -0.0532985000
_diffrn_orient_matrix_UB_23      0.1047893000
_diffrn_orient_matrix_UB_31      -0.1932770000
_diffrn_orient_matrix_UB_32      0.0600616000
_diffrn_orient_matrix_UB_33      -0.0160503000
_diffrn_radiation_collimation    'VariMax VHF mirror optic'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24810
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.388
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'rotating anode'
_diffrn_source_current           30
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'MicroMax 007 HF'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    2.785
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5011
_refine_ls_number_restraints     442
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0532
_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^)+(0.0537P)^2^+1.0479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1339
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4599
_reflns_number_total             5011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc02257a2.cif
_cod_data_source_block           abjemc
_cod_depositor_comments          'Adding full bibliography for 7128543.cif.'
_cod_original_cell_volume        1217.39(4)
_cod_database_code               7128543
_nottingham_internal_coll_name   ABJEMC
_nottingham_internal_coll_number 16116
_nottingham_internal_coll_client AB/JEM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 0.50'
_nottingham_internal_coll_frame_width 'in, 0.50'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   19/05/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 08/06/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 8/6/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 26/9/2016
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 26/9/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 26/9/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C23 H23 N O7'
_chemical_oxdiff_usercomment
'ABJEMC #16116 MM-187 IN FOMBLIN FILM ON A MICROMOUNT FOR AB/JEM'
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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. Restrained distances
 C6-C2 \\sim C6A-C2A
 with sigma of 0.02
 C7A-C2A \\sim C7-C2
 with sigma of 0.02
 O1A-C2A \\sim O1-C2
 with sigma of 0.02
 O1-C5 \\sim O1A-C5A
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C4-C3 \\sim C4A-C3A
 with sigma of 0.02
 C3A-C2A \\sim C3-C2
 with sigma of 0.02
 C8-C3 \\sim C8A-C3A
 with sigma of 0.02
 O9-C8 \\sim O9A-C8A
 with sigma of 0.02
 C8-C10 \\sim C8A-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O1A \\sim C2 \\sim C2A \\sim C3 \\sim C3A \\sim C4 \\sim C4A \\sim C5
\\sim C5A \\sim C6 \\sim C6A \\sim C7 \\sim C7A \\sim C8 \\sim C8A \\sim O9
\\sim O9A \\sim C10: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
4. Rigid body (RIGU) restrains
 O1, O1A, C2, C2A, C3, C3A, C4, C4A, C5, C5A, C6, C6A, C7, C7A, C8, C8A, O9,
 O9A, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O1A)=Sof(C2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=
 Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C7A)=Sof(H7AA)=
 Sof(H7AB)=Sof(H7AC)=Sof(C8A)=Sof(O9A)=Sof(H10A)=1-FVAR(1)
 Sof(O1)=Sof(C2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=
 Sof(H5B)=Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=
 Sof(C8)=Sof(O9)=Sof(H10)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C3(H3), C3A(H3A)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4A(H4AA,H4AB), C5(H5A,H5B), C5A(H5AA,H5AB), C32(H32A,H32B)
6.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C10(H10A), C11(H11), C13(H13), C16(H16), C17(H17), C24(H24),
 C25(H25), C27(H27), C28(H28)
6.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC), C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC),
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              95024
_olex2_date_sample_data_collection 2016-05-19
_olex2_date_sample_submission    2016-05-09
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_original_sample_id AB1703
_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 1.534
_oxdiff_exptl_absorpt_empirical_full_min 0.781