Borrowing hydrogen <i>C</i>-alkylation with secondary saturated heterocyclic alcohols.
François, Jordan; Jacolot, Maïwenn; Popowycz, Florence; Organic & biomolecular chemistry 22 (2024) 4502–4507; doi:10.1039/d4ob00543k

data_7159928
_publ_section_title
;
 Borrowing hydrogen <i>C</i>-alkylation with secondary saturated
 heterocyclic alcohols.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4502
_journal_page_last               4507
_journal_paper_doi               10.1039/d4ob00543k
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H22 I N O2'
_chemical_formula_sum            'C16 H22 I N O2'
_chemical_formula_weight         387.24
_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     dual
_audit_creation_date             2022-12-14
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-04-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                80.907(3)
_cell_angle_beta                 89.846(2)
_cell_angle_gamma                80.988(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6026(3)
_cell_length_b                   10.9032(3)
_cell_length_c                   15.9038(5)
_cell_measurement_reflns_used    25455
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.1770
_cell_measurement_theta_min      5.4000
_cell_volume                     1623.48(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.941
_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    -41.00  34.00   0.50    0.50    --  -43.82  54.00  84.00  150
  2  \w    -33.00  41.00   0.50    0.50    --   44.69 -54.00 -59.00  148
  3  \w   -165.00 -83.00   0.50    2.50    --  -87.52 -54.00 -59.00  164
  4  \w    -41.00 -10.00   0.50    2.50    --  -87.52  54.00  84.00   62
  5  \w    105.00 178.00   0.50    2.50    --  111.23  54.00  84.00  146
  6  \w    -21.00  10.00   0.50    0.50    --   10.00  90.00 -63.98   62
  7  \w    -25.00   2.00   0.50    0.50    --   14.00 102.00 163.15   54
  8  \w     -5.00  21.00   0.50    0.50    --   18.00  77.00-150.84   52
  9  \w     -5.00  22.00   0.50    0.50    --   18.00  76.00 -40.21   54
 10  \w     -5.00  21.00   0.50    0.50    --   18.00  77.00 175.63   52
 11  \w     -6.00  20.00   0.50    0.50    --   18.00  78.00  77.68   52
 12  \w      3.00  33.00   0.50    0.50    --   22.00  68.00-177.91   60
 13  \w     12.00  38.00   0.50    0.50    --   30.00  67.00-101.68   52
 14  \w     16.00  43.00   0.50    0.50    --   34.00  65.00  -8.71   54
 15  \w     21.00  47.00   0.50    0.50    --   38.00  63.00 -29.80   52
 16  \w     26.00  57.00   0.50    0.50    --   42.00  60.00 106.45   62
 17  \w    -19.00  37.00   0.50    0.50    --  -43.82  38.00-150.00  112
 18  \w     28.00  54.00   0.50    0.50    --   44.69  61.00 -42.61   52
 19  \w   -124.00 -31.00   0.50    0.50    --  -46.00 -52.00  33.49  186
 20  \w   -157.00-102.00   0.50    2.50    --  -87.52 -77.00  60.00  110
 21  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -30.00  186
 22  \w   -157.00-102.00   0.50    2.50    --  -87.52 -77.00-150.00  110
 23  \w   -157.00-102.00   0.50    2.50    --  -87.52 -77.00 -90.00  110
 24  \w    -51.00 -12.00   0.50    2.50    --  -87.52  61.00-180.00   78
 25  \w    -51.00 -12.00   0.50    2.50    --  -87.52  61.00 -90.00   78
 26  \w     29.00  92.00   0.50    2.50    --  101.51 -95.00  60.00  126
 27  \w    124.00 171.00   0.50    2.50    --  101.51  77.00 -30.00   94
 28  \w    112.00 176.00   0.50    2.50    --  101.51 125.00 150.00  128
 29  \w     34.00 101.00   0.50    2.50    --  101.51-125.00-180.00  134
 30  \w    109.00 177.00   0.50    2.50    --  101.51  61.00 -60.00  136
 31  \w    124.00 171.00   0.50    2.50    --  101.51  77.00-120.00   94
 32  \w     34.00 101.00   0.50    2.50    --  101.51-125.00 -90.00  134
 33  \w     29.00  92.00   0.50    2.50    --  101.51 -95.00   0.00  126
 34  \w    109.00 177.00   0.50    2.50    --  101.51  61.00  30.00  136
 35  \w     29.00  92.00   0.50    2.50    --  101.51 -95.00 -90.00  126
 36  \w    105.00 178.00   0.50    2.50    --  101.51  54.00  84.00  146
 37  \w    109.00 178.00   0.50    2.50    --  111.23  61.00 150.00  138
 38  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00 -30.00  106
 39  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00-180.00  106
 40  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00-120.00  106
 41  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00 -60.00  106
 42  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00 150.00  106
 43  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00-150.00  106
 44  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00  30.00  106
 45  \w     42.00  75.00   0.50    2.50    --  111.23 -77.00  90.00   66
 46  \w    109.00 178.00   0.50    2.50    --  111.23  61.00  60.00  138
 47  \w     39.00  92.00   0.50    2.50    --  111.23 -95.00  90.00  106
 48  \w     17.00  44.00   0.50    0.50    --   34.00  64.00 142.74   54
 49  \w     28.00  57.00   0.50    0.50    --   44.69  60.00  13.98   58
 50  \w     28.00  57.00   0.50    0.50    --   44.69  60.00  45.22   58
 51  \w     29.00  59.00   0.50    0.50    --   44.69  59.00-177.32   60
 52  \w     30.00  60.00   0.50    0.50    --   44.69  55.00-131.60   60
 53  \w     29.00  59.00   0.50    0.50    --   44.69  59.00 160.16   60
 54  \w     28.00  57.00   0.50    0.50    --   44.69  60.00 -96.58   58
 55  \w     29.00  59.00   0.50    0.50    --   44.69  59.00-153.28   60
 56  \w     30.00  57.00   0.50    0.50    --   46.00  60.00  76.24   54
 57  \w     60.00 153.00   0.50    0.50    --   74.00  50.00 -94.92  186
 58  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-120.00  186
 59  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  60.00  186
 60  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 120.00  186
 61  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -90.00  186
 62  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-150.00  186
 63  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  30.00  186
 64  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00   0.00  186
 65  \w    -74.00 -13.00   0.50    2.50    --  -87.52 125.00   0.00  122
 66  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 150.00  186
 67  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00  90.00  186
 68  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00-180.00  186
 69  \w    -67.00 -18.00   0.50    2.50    --  -87.52  77.00  30.00   98
 70  \w    -74.00 -13.00   0.50    2.50    --  -87.52 125.00-180.00  122
 71  \w   -167.00 -74.00   0.50    2.50    --  -87.52 -45.00 -60.00  186
 72  \w   -173.00 -80.00   0.50    2.50    --  -94.50 -48.00 142.02  186
 73  \w   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00 177.21  184
 74  \w   -173.00 -80.00   0.50    2.50    --  -94.50 -51.00 117.14  186
 75  \w   -173.00 -80.00   0.50    2.50    --  -94.50 -51.00 -40.77  186
 76  \w   -172.00 -83.00   0.50    2.50    --  -94.50 -55.00  61.89  178
 77  \w   -173.00 -80.00   0.50    2.50    --  -94.50 -49.00-120.56  186
 78  \w   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00  68.19  184
 79  \w     88.00 178.00   0.50    2.50    --  101.51  45.00 -30.00  180
 80  \w     88.00 178.00   0.50    2.50    --  101.51  45.00  30.00  180
 81  \w     52.00 136.00   0.50    2.50    --  101.51  15.00-150.00  168
 82  \w     88.00 178.00   0.50    2.50    --  101.51  45.00  60.00  180
 83  \w     88.00 178.00   0.50    2.50    --  101.51  45.00-120.00  180
 84  \w     88.00 178.00   0.50    2.50    --  101.51  45.00 -60.00  180
 85  \w    124.00 171.00   0.50    2.50    --  101.51  77.00-150.00   94
 86  \w     85.00 166.00   0.50    2.50    --  101.51  30.00 -60.00  162
 87  \w     62.00 136.00   0.50    2.50    --  111.23  15.00 -90.00  148
 88  \w     -5.00  22.00   0.50    0.50    --   18.00  76.00 133.25   54
 89  \w     12.00  38.00   0.50    0.50    --   30.00  67.00  67.83   52
 90  \w     17.00  44.00   0.50    0.50    --   34.00  64.00 -53.19   54
 91  \w     21.00  47.00   0.50    0.50    --   38.00  63.00-127.34   52
 92  \w    -66.00  21.00   0.50    0.50    --  -43.82  77.00 -30.00  174
 93  \w    -19.00  37.00   0.50    0.50    --  -43.82  38.00  30.00  112
 94  \w    -19.00  37.00   0.50    0.50    --  -43.82  38.00 150.00  112
 95  \w     28.00  57.00   0.50    0.50    --   44.69  60.00 141.57   58
 96  \w     30.00  57.00   0.50    0.50    --   46.00  60.00  -7.54   54
 97  \w     34.00  60.00   0.50    0.50    --   50.00  57.00 -32.60   52
 98  \w   -172.00 -80.00   0.50    2.50    --  -94.50 -52.00-165.44  184
 99  \w   -169.00 -92.00   0.50    2.50    --  -94.50 -63.00 117.51  154
100  \w   -173.00 -80.00   0.50    2.50    --  -94.50 -49.00 148.04  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1114665000
_diffrn_orient_matrix_UB_12      0.0448457000
_diffrn_orient_matrix_UB_13      -0.0623594000
_diffrn_orient_matrix_UB_21      -0.0846228000
_diffrn_orient_matrix_UB_22      0.1340900000
_diffrn_orient_matrix_UB_23      -0.0137269000
_diffrn_orient_matrix_UB_31      0.0825434000
_diffrn_orient_matrix_UB_32      0.0317780000
_diffrn_orient_matrix_UB_33      0.0745088000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            47510
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.996
_diffrn_reflns_theta_min         5.385
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    15.506
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.040
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.091
_refine_diff_density_min         -1.391
_refine_diff_density_rms         0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0853P)^2^+8.0133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5557
_reflns_number_total             6462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00543k2.cif
_cod_data_source_block           jfr659
_cod_depositor_comments          'Adding full bibliography for 7159928.cif.'
_cod_database_code               7159928
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H22 I1 N1 O2'
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.052
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C26(H26), C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B),
 C15(H15A,H15B), C23(H23A,H23B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B),
  C30(H30A,H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), N2(H2A), C18(H18), C19(H19), C21(H21),
  C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              37554
_olex2_submission_original_sample_id JFR659
_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 2.800
_oxdiff_exptl_absorpt_empirical_full_min 0.423