1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes
Yao, Yongqi; Yang, Wen; Lin, Qifu; Yang, Weitao; Li, Huanyong; Wang, Lin; Gu, Fenglong; Yang, Dingqiao; Organic Chemistry Frontiers 6 (2019) 3360–; doi:10.1039/C9QO00660E

data_1554995
_publ_section_title
;
 1,3-Dipolar cycloaddition of nitrones to oxa(aza)bicyclic alkenes
;
_journal_issue                   19
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3360
_journal_paper_doi               10.1039/C9QO00660E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C23 H18 Cl N O2'
_chemical_formula_sum            'C23 H18 Cl N O2'
_chemical_formula_weight         375.83
_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             2019-03-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-08 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_cell_angle_alpha                87.027(6)
_cell_angle_beta                 65.546(8)
_cell_angle_gamma                82.335(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2832(7)
_cell_length_b                   10.0044(7)
_cell_length_c                   11.1070(9)
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    173(13)
_cell_measurement_theta_max      28.7860
_cell_measurement_theta_min      4.0220
_cell_volume                     930.61(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.960
_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     35.00  68.00   1.00    5.00    --   15.49 178.00  30.00   33
  2  \w    -52.00  80.00   1.00    5.00    --   15.49   0.00 -60.00  132
  3  \w    -28.00   8.00   1.00    5.00    --  -16.28  38.00-180.00   36
  4  \w     -2.00  42.00   1.00    5.00    --   15.34 -77.00  30.00   44
  5  \w     53.00  78.00   1.00    5.00    --   15.34  57.00 150.00   25
  6  \w      3.00  44.00   1.00    5.00    --   15.34  57.00 150.00   41
  7  \w    -75.00  -3.00   1.00    5.00    --  -15.96 -57.00 -90.00   72
  8  \w    -21.00   1.00   1.00    5.00    --  -15.96 -99.00-180.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0250204000
_diffrn_orient_matrix_UB_12      0.0302757000
_diffrn_orient_matrix_UB_13      0.0432834000
_diffrn_orient_matrix_UB_21      0.0574752000
_diffrn_orient_matrix_UB_22      -0.0568668000
_diffrn_orient_matrix_UB_23      -0.0072234000
_diffrn_orient_matrix_UB_31      0.0567830000
_diffrn_orient_matrix_UB_32      0.0311005000
_diffrn_orient_matrix_UB_33      -0.0547376000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7976
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.369
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0584
_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^)+(0.0398P)^2^+0.6177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1381
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2911
_reflns_number_total             3900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00660e2.cif
_cod_data_source_block           exp_6478
_cod_original_cell_volume        930.61(13)
_cod_database_code               1554995
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C23(H23), C22(H22), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C11(H11), C12(H12), C5(H5), C3(H3), C2(H2), C10(H10),
 C6(H6), C20(H20), C17(H17), C19(H19), C18(H18)
;
_shelx_res_checksum              82851
_shelx_hkl_checksum              6703
_olex2_date_sample_data_collection 2019-03-05
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.816