Facile access to a heterocyclic, sp(3)-rich chemical scaffold via a tandem condensation/intramolecular nitrone-alkene [3+2] cycloaddition strategy.
Rawling, M. J.; Storr, T. E.; Bawazir, W. A.; Cully, S. J.; Lewis, W.; Makki, M. S. I. T.; Strutt, I. R.; Jones, G.; Hamza, D.; Stockman, R. A.; Chemical communications (Cambridge, England) 51 (2015) 12867–12870; doi:10.1039/c5cc05070g

data_7117584
_publ_section_title
;
 Facile access to a heterocyclic, sp(3)-rich chemical scaffold via a
 tandem condensation/intramolecular nitrone-alkene [3+2] cycloaddition
 strategy.
;
_journal_issue                   64
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12867
_journal_page_last               12870
_journal_paper_doi               10.1039/c5cc05070g
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C18 H24 N2 O2'
_chemical_formula_sum            'C18 H24 N2 O2'
_chemical_formula_weight         300.39
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-04-21 deposited with the CCDC.
2015-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                107.964(7)
_cell_angle_beta                 98.204(8)
_cell_angle_gamma                97.133(7)
_cell_formula_units_Z            2
_cell_length_a                   8.0233(8)
_cell_length_b                   8.5269(6)
_cell_length_c                   12.1531(9)
_cell_measurement_reflns_used    5259
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.4390
_cell_measurement_theta_min      3.8900
_cell_volume                     770.22(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_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                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega  -31.00   24.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000   30.0000 55

  2 omega  -70.00  -18.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000   60.0000 52

  3 omega  -46.00  -18.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  -90.0000 28

  4 omega  -29.00   -3.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -90.0000 -147.1678 26

  5 omega  -93.00  -54.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  -90.0000 39

  6 omega  -87.00  -13.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000 -150.0000 74

  7 omega -107.00  -80.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000   60.0000 27

  8 omega    2.00   92.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4304 -125.0000  150.0000 90

  9 omega    9.00   34.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   85.0000 -130.4479 25

 10 omega   11.00   36.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000  -33.8609 25

 11 omega   14.00   41.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000    8.1081 27

 12 omega   19.00   45.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   82.0000   96.2211 26

 13 omega   19.00   44.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   81.0000  154.9889 25

 14 omega   29.00   54.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000 -148.2209 25

 15 omega   76.00  124.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000 -148.2209 48

 16 omega   29.00   81.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -15.0448 52

 17 omega   32.00   62.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  175.0697 30

 18 omega   31.00   62.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -120.7387 31

 19 omega   84.00  127.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -15.0448 43

 20 omega   36.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000  -70.4393 36

 21 omega   32.00   58.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000   35.9575 26

 22 omega   32.00   64.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  120.6555 32

 23 omega   38.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000   78.1729 31

 24 omega   38.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -96.9841 27

 25 omega   41.00   74.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000  134.4010 33

 26 omega   43.00   70.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   68.0000   30.9778 27

 27 omega   60.00   87.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   64.0000   41.8181 27

 28 omega   66.00  151.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   71.0000   72.0085 85

 29 omega   80.00  172.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -30.0000 92

 30 omega   67.00   94.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  -30.0000 27

 31 omega   85.00  173.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000   30.0000 88

 32 omega   48.00   84.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -150.0000 36

 33 omega   82.00  165.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   45.0000  150.0000 83

 34 omega   79.00  104.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  150.0000 25

 35 omega   79.00  107.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -60.0000 28

 36 omega   75.00  100.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -60.0000 25

 37 omega   79.00  137.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -90.0000 58

 38 omega   74.00  176.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -90.0000 102

 39 omega   25.00   87.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000  120.0000 62

 40 omega  124.00  159.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 35

 41 omega   78.00  116.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 38

 42 omega   36.00   95.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  -60.0000 59

 43 omega   74.00  175.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -150.0000 101

 44 omega   76.00  141.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -180.0000 65

 45 omega   74.00  100.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000 -120.0000 26

 46 omega  122.00  149.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000  -60.0000 27

 47 omega   78.00  104.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000 -180.0000 26

 48 omega   33.00  107.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -94.0000 -180.0000 74

 49 omega  119.00  162.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   90.0000 43

 50 omega   35.00  132.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -77.0000 -150.0000 97

 51 omega   74.00  107.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   77.0000   90.0000 33

 52 omega   38.00  121.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000 -125.0000   90.0000 83
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      -0.1282903000
_diffrn_orient_matrix_UB_12      -0.1655068000
_diffrn_orient_matrix_UB_13      -0.0600703000
_diffrn_orient_matrix_UB_21      -0.1052843000
_diffrn_orient_matrix_UB_22      0.0507179000
_diffrn_orient_matrix_UB_23      0.0977930000
_diffrn_orient_matrix_UB_31      -0.1064522000
_diffrn_orient_matrix_UB_32      0.0854279000
_diffrn_orient_matrix_UB_33      -0.0725528000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10903
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.880
_diffrn_reflns_theta_min         3.896
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.1566
_exptl_crystal_size_min          0.0846
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0854
_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^)+(0.1537P)^2^+0.6321P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2434
_refine_ls_wR_factor_ref         0.2499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2661
_reflns_number_total             3053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05070g2.cif
_cod_data_source_block           mjrrsc
_cod_original_cell_volume        770.22(11)
_cod_database_code               7117584
_nottingham_internal_coll_name   MJRRSC
_nottingham_internal_coll_number 13960
_nottingham_internal_coll_client MJR/RS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '25.0000, 100.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   12/09/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 02/10/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 2/10/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 15/1/2015
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 15/1/2015
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 15/1/2015
_chemical_oxdiff_formula         'C18 H25 N2 O2'
_chemical_oxdiff_usercomment
'MJRRSC #13960 GVB-280 IN FOMBLIN FILM ON A MICROMOUNT FOR MJR/RS'
_reflns_odcompleteness_completeness 99.96
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              96315
_shelx_shelxl_version_number     2014/7
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'