Transition metal-free synthesis of sterically hindered allylarenes from 5-hexene-2-one.
Shaw, Ranjay; Althagafi, Ismail; Elagamy, Amr; Rai, Reeta; Shah, Chandan; Nemaysh, Vishal; Singh, Harpreet; Pratap, Ramendra; Organic & biomolecular chemistry 18 (2020) 6276–6286; doi:10.1039/d0ob01318h

data_7157596
_publ_section_title
;
 Transition metal-free synthesis of sterically hindered allylarenes from
 5-hexene-2-one.
;
_journal_issue                   32
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6276
_journal_page_last               6286
_journal_paper_doi               10.1039/d0ob01318h
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 N S'
_chemical_formula_sum            'C18 H17 N S'
_chemical_formula_weight         279.40
_chemical_name_systematic        prs315B
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-02-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-27 deposited with the CCDC.	2020-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.519(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0216(3)
_cell_length_b                   10.1719(3)
_cell_length_c                   17.3180(7)
_cell_measurement_reflns_used    6153
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      28.2260
_cell_measurement_theta_min      3.5730
_cell_volume                     1557.21(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.8482
_diffrn_measured_fraction_theta_max 0.8482
_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    -44.00  53.00   1.00    1.00    --  -15.32  77.00 120.00   97
  2  \w     13.00  80.00   1.00    1.00    --   19.15  57.00  90.00   67
  3  \w      4.00  83.00   1.00    1.00    --   19.15  57.00  30.00   79
  4  \w      1.00  88.00   1.00    1.00    --   19.15  57.00 -90.00   87
  5  \w      8.00  88.00   1.00    1.00    --   19.15  57.00-180.00   80
  6  \w    -12.00  18.00   1.00    1.00    --  -15.32 -99.00 -90.00   30
  7  \w    -38.00  27.00   1.00    1.00    --   19.15 -57.00 -90.00   65
  8  \w    -23.00  60.00   1.00    1.00    --   19.15 -99.00-120.00   83
  9  \w    -24.00  60.00   1.00    1.00    --   19.15 -99.00  30.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0583333000
_diffrn_orient_matrix_UB_12      -0.0078283000
_diffrn_orient_matrix_UB_13      0.0338074000
_diffrn_orient_matrix_UB_21      -0.0500790000
_diffrn_orient_matrix_UB_22      0.0211418000
_diffrn_orient_matrix_UB_23      0.0242739000
_diffrn_orient_matrix_UB_31      -0.0229753000
_diffrn_orient_matrix_UB_32      -0.0660011000
_diffrn_orient_matrix_UB_33      0.0037733000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22455
_diffrn_reflns_theta_full        29.4596
_diffrn_reflns_theta_max         29.46
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.1917
_exptl_crystal_description       block
_exptl_crystal_F_000             592.6898
_exptl_crystal_preparation
'slow evaporation in 1:9 ethyl acetate in hexane'
_exptl_crystal_recrystallization_method 'crystaline clear blocks'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.1979
_refine_diff_density_min         -0.1912
_refine_diff_density_rms         0.0499
_refine_ls_d_res_high            0.7226
_refine_ls_d_res_low             5.9134
_refine_ls_goodness_of_fit_ref   1.0456
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    25
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0456
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.1170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                2770
_reflns_number_total             3661
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ob01318h2.cif
_cod_data_source_block           PRS-315B
_cod_depositor_comments
;
Adding full bibliography for 7157595--7157596.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.483 H2.345 N0.138 S0.138'
_cod_original_formula_weight         38.54
_cod_original_formula_moiety         '0.14(C18 H17 N S)'
_cod_original_formula_units_Z            29
_cod_database_code               7157596
_chemical_oxdiff_formula         'C18 H17 N S'
_chemical_oxdiff_usercomment     05-01-2018
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C7aa(H7aa,H7ab)
2.b Aromatic/amide H refined with riding coordinates:
 C4aa(H4aa), C0ba(H0ba), C4ba(H4ba), C3ba(H3ba), C1ba(H1ba), C9aa(H9aa),
 C2ba(H2ba)
2.c Idealised Me refined as rotating group:
 C(Ha,Hb,Hc), C7ba(H7ba,H7bb,H7bc)
;
_olex2_exptl_crystal_mounting_method 'No need'
_olex2_submission_original_sample_id 'PRS 315 B'
_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 1.200
_oxdiff_exptl_absorpt_empirical_full_min 0.771