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_7157595
_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         'C23 H26 N2'
_chemical_formula_sum            'C23 H26 N2'
_chemical_formula_weight         330.48
_chemical_name_systematic        abc
_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_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2020-03-23
_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                94.077(5)
_cell_angle_beta                 104.535(6)
_cell_angle_gamma                105.981(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2991(6)
_cell_length_b                   9.0692(6)
_cell_length_c                   13.6609(9)
_cell_measurement_reflns_used    2336
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.2260
_cell_measurement_theta_min      3.9130
_cell_volume                     945.91(12)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9974
_diffrn_measured_fraction_theta_max 0.8707
_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     -3.00  77.00   1.00    3.00    --   18.84  38.00   0.00   80
  2  \w      1.00  88.00   1.00    3.00    --   18.84  77.00  60.00   87
  3  \w      1.00  86.00   1.00    3.00    --   18.84  38.00 -90.00   85
  4  \w      7.00  85.00   1.00    3.00    --   18.84  38.00-180.00   78
  5  \w    -12.00  24.00   1.00    3.00    --  -15.17 -99.00 -60.00   36
  6  \w    -16.00  58.00   1.00    3.00    --   18.84 -99.00 -90.00   74
  7  \w    -17.00  59.00   1.00    3.00    --   18.84 -99.00   0.00   76
  8  \w    -18.00  63.00   1.00    3.00    --   18.84-105.00 117.19   81
  9  \w    -49.00  15.00   1.00    3.00    --   18.84 -57.00-180.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002678000
_diffrn_orient_matrix_UB_12      -0.0365255000
_diffrn_orient_matrix_UB_13      0.0442356000
_diffrn_orient_matrix_UB_21      0.0445704000
_diffrn_orient_matrix_UB_22      0.0728638000
_diffrn_orient_matrix_UB_23      0.0314184000
_diffrn_orient_matrix_UB_31      -0.0812452000
_diffrn_orient_matrix_UB_32      0.0113535000
_diffrn_orient_matrix_UB_33      -0.0000790000
_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  0.0423
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14072
_diffrn_reflns_theta_full        29.5040
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_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 yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1602
_exptl_crystal_description       block
_exptl_crystal_F_000             356.1248
_exptl_crystal_preparation       'IN ethylacetate and hexane'
_exptl_crystal_recrystallization_method ABCD
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3158
_refine_diff_density_min         -0.3276
_refine_diff_density_rms         0.0803
_refine_ls_d_res_high            0.7216
_refine_ls_d_res_low             5.9173
_refine_ls_goodness_of_fit_ref   1.0431
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0431
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0555P)^2^+0.0798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2572
_reflns_number_total             4601
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d0ob01318h2.cif
_cod_data_source_block           PRS-302
_cod_depositor_comments
'Adding full bibliography for 7157595--7157596.cif.'
_cod_database_code               7157595
_chemical_oxdiff_formula         'C23 H26 N2'
_chemical_oxdiff_usercomment     01-08-2018
_reflns_odcompleteness_completeness 99.74
_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:
 C00A(H00a,H00b), C00D(H00d,H00e), C00G(H00g,H00h), C00I(H00i,H00j), C00K(H00l,
 H00m), C00L(H00n,H00o)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00C(H00C), C00F(H00F), C00J(H00k), C00N(H00s)
2.c Idealised Me refined as rotating group:
 C00M(H00p,H00q,H00r), C00O(H00t,H00u,H00v)
;
_olex2_exptl_crystal_mounting_method ABCD
_olex2_submission_original_sample_id 'PRS 302'
_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 1.093
_oxdiff_exptl_absorpt_empirical_full_min 0.929