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_7244108
_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         'C27 H22 N2 O6'
_chemical_formula_sum            'C27 H22 N2 O6'
_chemical_formula_weight         470.46
_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             2020-08-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2021-10-31 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                102.291(16)
_cell_angle_beta                 100.426(16)
_cell_angle_gamma                103.17(2)
_cell_formula_units_Z            2
_cell_length_a                   9.838(2)
_cell_length_b                   10.401(2)
_cell_length_c                   12.2553(17)
_cell_measurement_reflns_used    2042
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.5310
_cell_measurement_theta_min      3.5560
_cell_volume                     1157.8(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)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_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 0.998
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details
;
  1 omega  -10.00   87.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509   57.0000   60.0000 97

  2 omega  -13.00   84.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509   38.0000 -150.0000 97

  3 omega  -14.00   18.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.3197  -99.0000 -180.0000 32

  4 omega  -54.00   38.00   1.0000   85.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8509  -57.0000  -90.0000 92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0349581000
_diffrn_orient_matrix_UB_12      -0.0051512000
_diffrn_orient_matrix_UB_13      0.0453244000
_diffrn_orient_matrix_UB_21      -0.0205803000
_diffrn_orient_matrix_UB_22      0.0602920000
_diffrn_orient_matrix_UB_23      -0.0037464000
_diffrn_orient_matrix_UB_31      -0.0646190000
_diffrn_orient_matrix_UB_32      -0.0401825000
_diffrn_orient_matrix_UB_33      -0.0407075000
_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  0.0542
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.472
_diffrn_reflns_theta_min         3.060
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.027(4)
_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   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.0512P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1540
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2871
_reflns_number_total             5376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08384h2.cif
_cod_data_source_block           psu-1120(aa-116)
_cod_depositor_comments
'Adding full bibliography for 7244108--7244111.cif.'
_cod_original_cell_volume        1157.9(4)
_cod_database_code               7244108
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.967
_reflns_odcompleteness_completeness 99.83
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              33634
_olex2_submission_special_instructions 'No special instructions were received'