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_7117583
_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         'C24 H28 N2 O2'
_chemical_formula_sum            'C24 H28 N2 O2'
_chemical_formula_weight         376.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90
_cell_angle_beta                 94.024(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8462(8)
_cell_length_b                   7.6966(5)
_cell_length_c                   22.1897(18)
_cell_measurement_reflns_used    3602
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.7120
_cell_measurement_theta_min      3.6830
_cell_volume                     2018.2(3)
_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      120.01(10)
_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 0.994
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
  1 omega  126.00  176.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  150.0000 25

  2 omega   94.00  158.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000    0.0000 32

  3 omega   85.00  111.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   30.0000  150.0000 13

  4 omega   48.00   86.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000  120.0000 19

  5 omega   37.00  131.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -61.0000  120.0000 47

  6 omega   82.00  172.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000   61.0000  -90.0000 45

  7 omega   72.00   98.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -45.0000 -150.0000 13

  8 omega   55.00   89.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000 -120.0000 17

  9 omega   38.00   64.00   2.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      104.5000  -30.0000  -90.0000 13

 10 omega   18.00  100.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6804   57.0000 -150.0000 41

 11 omega  -14.00   12.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 13

 12 omega  -28.00   72.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6804  -77.0000   60.0000 50
;
_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      0.0457625000
_diffrn_orient_matrix_UB_12      -0.1690816000
_diffrn_orient_matrix_UB_13      -0.0261868000
_diffrn_orient_matrix_UB_21      0.0959773000
_diffrn_orient_matrix_UB_22      -0.0034468000
_diffrn_orient_matrix_UB_23      0.0506121000
_diffrn_orient_matrix_UB_31      -0.0754382000
_diffrn_orient_matrix_UB_32      -0.1066934000
_diffrn_orient_matrix_UB_33      0.0400755000
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8087
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.127
_diffrn_reflns_theta_min         4.363
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.861
_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    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3944
_exptl_crystal_size_mid          0.2707
_exptl_crystal_size_min          0.0743
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0481P)^2^+0.5125P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3514
_reflns_number_total             3961
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc05070g2.cif
_cod_data_source_block           mjrrsb
_cod_database_code               7117583
_nottingham_internal_coll_name   MJRRSB
_nottingham_internal_coll_number 13930
_nottingham_internal_coll_client MJR/RS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '6.0000, 2.0000'
_nottingham_internal_coll_frame_width 2.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   26/08/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 26/08/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 26/8/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 26/8/2014
_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         'C24 H28 N2 O2'
_chemical_oxdiff_usercomment
'MJRRSB #13930 GVB-262 IN FOMBLIN FILM ON A MICROMOUNT FOR MJR/RS'
_reflns_odcompleteness_completeness 99.46
_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 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), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              47050
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'