Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization of functionalized spiropyrido[2,1-<i>b</i>][1,3]oxazine-pyrroles and related products.
Galeev, Andrew R.; Moroz, Anna A.; Dmitriev, Maksim V.; Maslivets, Andrey N.; RSC advances 12 (2021) 578–587; doi:10.1039/d1ra08384h

data_7244109
_publ_section_title
;
 Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization
 of functionalized spiropyrido[2,1-<i>b</i>][1,3]oxazine-pyrroles and
 related products.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              578
_journal_page_last               587
_journal_paper_doi               10.1039/d1ra08384h
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C30 H21 N3 O5'
_chemical_formula_sum            'C30 H21 N3 O5'
_chemical_formula_weight         503.50
_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     direct
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-10-31 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                99.666(8)
_cell_angle_beta                 96.992(8)
_cell_angle_gamma                94.581(8)
_cell_formula_units_Z            4
_cell_length_a                   11.4672(12)
_cell_length_b                   14.0604(14)
_cell_length_c                   15.6426(15)
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1910
_cell_measurement_theta_min      2.2830
_cell_volume                     2454.8(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details
;
  1 omega   14.00   57.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -99.0000   60.0000 43

  2 omega   -4.00   50.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -77.0000  150.0000 54

  3 omega  -15.00   21.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978  -99.0000  -90.0000 36

  4 omega -104.00   78.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3978    0.0000 -150.0000 182

  5 omega   67.00  106.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  178.0000    0.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0151696000
_diffrn_orient_matrix_UB_12      -0.0503239000
_diffrn_orient_matrix_UB_13      -0.0021106000
_diffrn_orient_matrix_UB_21      0.0463705000
_diffrn_orient_matrix_UB_22      -0.0105772000
_diffrn_orient_matrix_UB_23      -0.0251172000
_diffrn_orient_matrix_UB_31      0.0392994000
_diffrn_orient_matrix_UB_32      0.0014615000
_diffrn_orient_matrix_UB_33      0.0390023000
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22145
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.486
_diffrn_reflns_theta_min         2.160
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         11448
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0706P)^2^+0.1863P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6772
_reflns_number_total             11448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08384h2.cif
_cod_data_source_block           psu-1278(r-440-r)
_cod_depositor_comments
'Adding full bibliography for 7244108--7244111.cif.'
_cod_database_code               7244109
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.950
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C28B)=Sof(H28E)=Sof(H28D)=Sof(H28F)=1-FVAR(1)
 Sof(C28A)=Sof(H28B)=Sof(H28C)=Sof(H28A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C22(H22), C22A(H22A)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C2A(H2A), C3A(H3A),
  C4A(H4A), C5A(H5A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A),
 C18A(H18A), C19A(H19A), C23A(H23A), C24A(H24A), C25A(H25A), C26A(H26A)
3.c Idealised Me refined as rotating group:
 C28(H28G,H28H,H28I), C30(H30D,H30E,H30F), C28A(H28B,H28C,H28A), C28B(H28E,
 H28D,H28F), C30A(H30A,H30B,H30C)
;
_shelx_res_checksum              76058
_olex2_submission_special_instructions 'No special instructions were received'