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_7121159
_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_absolute_configuration rmad
_chemical_formula_moiety         'C26 H27 N3 O4 S'
_chemical_formula_sum            'C26 H27 N3 O4 S'
_chemical_formula_weight         477.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6243(6)
_cell_length_b                   10.5297(7)
_cell_length_c                   25.811(2)
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4828
_cell_measurement_theta_min      2.8349
_cell_volume                     2343.9(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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0359862000
_diffrn_orient_matrix_UB_12      -0.0396638000
_diffrn_orient_matrix_UB_13      0.0186735000
_diffrn_orient_matrix_UB_21      0.0027150000
_diffrn_orient_matrix_UB_22      0.0515983000
_diffrn_orient_matrix_UB_23      0.0176455000
_diffrn_orient_matrix_UB_31      -0.0738758000
_diffrn_orient_matrix_UB_32      -0.0174572000
_diffrn_orient_matrix_UB_33      0.0097480000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            16008
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.84
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85554
_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    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack (1983), 1831 Friedel pairs'
_refine_ls_abs_structure_Flack   0.10(8)
_refine_ls_extinction_coef       0.0187(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0478P)^2^+0.4055P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                3643
_reflns_number_total             4297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc09488d2.cif
_cod_data_source_block           161101_sgr4_100b
_cod_depositor_comments
'Adding full bibliography for 7121158--7121162.cif.'
_cod_original_cell_volume        2344.0(3)
_cod_database_code               7121159
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 C(H,H,H) groups
2. Restrained distances
 H1-O1
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18),
 C21(H21), C22(H22), C24(H24), C25(H25)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;