A copper-catalyzed reaction of 3-diazoindolin-2-imines with 2-(phenylamino)ethanols: convenient access to spiro[indoline-3,2'-oxazolidin]-2-imines.
Sheng, Guorong; Ma, Shicong; Bai, Songlin; Mao, Jianming; Lu, Ping; Wang, Yanguang; Chemical communications (Cambridge, England) 54 (2018) 1529–1532; doi:10.1039/c7cc09488d

data_7121160
_publ_section_title
;
 A copper-catalyzed reaction of 3-diazoindolin-2-imines with
 2-(phenylamino)ethanols: convenient access to
 spiro[indoline-3,2'-oxazolidin]-2-imines.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1529
_journal_page_last               1532
_journal_paper_doi               10.1039/c7cc09488d
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C27 H29 N3 O3 S'
_chemical_formula_sum            'C27 H29 N3 O3 S'
_chemical_formula_weight         475.59
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-01
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_audit_update_record
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2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                109.645(8)
_cell_angle_beta                 100.679(7)
_cell_angle_gamma                113.710(8)
_cell_formula_units_Z            2
_cell_length_a                   11.0863(10)
_cell_length_b                   11.6603(10)
_cell_length_c                   11.8746(10)
_cell_measurement_reflns_used    2216
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.2930
_cell_measurement_theta_min      3.0200
_cell_volume                     1228.8(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -69.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000   90.0000 90

  2 omega  -12.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000   30.0000 86

  3 omega  -62.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000 -150.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0597918000
_diffrn_orient_matrix_UB_12      0.0610253000
_diffrn_orient_matrix_UB_13      0.0085641000
_diffrn_orient_matrix_UB_21      -0.0426316000
_diffrn_orient_matrix_UB_22      0.0027874000
_diffrn_orient_matrix_UB_23      -0.0503916000
_diffrn_orient_matrix_UB_31      -0.0165247000
_diffrn_orient_matrix_UB_32      0.0429421000
_diffrn_orient_matrix_UB_33      0.0453295000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7663
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.026
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0564P)^2^+0.1419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1316
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_reflns_number_gt                3417
_reflns_number_total             4479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09488d2.cif
_cod_data_source_block           170601_sgr4_189a
_cod_depositor_comments
'Adding full bibliography for 7121158--7121162.cif.'
_cod_original_cell_volume        1228.8(2)
_cod_database_code               7121160
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.926
_reflns_odcompleteness_completeness 99.62
_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:
 C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              21118
_olex2_submission_special_instructions 'No special instructions were received'