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_7121162
_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 unk
_chemical_formula_moiety         'C19 H20 N2 O2'
_chemical_formula_sum            'C19 H20 N2 O2'
_chemical_formula_weight         308.37
_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
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-09-13 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5082(14)
_cell_length_b                   9.5276(15)
_cell_length_c                   18.393(3)
_cell_measurement_reflns_used    1236
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4801
_cell_measurement_theta_min      3.2167
_cell_volume                     1666.2(5)
_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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 5.1796
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -75.00   21.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.7965  -77.0000   30.0000 96
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0085617000
_diffrn_orient_matrix_UB_12      -0.0739435000
_diffrn_orient_matrix_UB_13      -0.0013361000
_diffrn_orient_matrix_UB_21      0.0170170000
_diffrn_orient_matrix_UB_22      -0.0006858000
_diffrn_orient_matrix_UB_23      0.0375342000
_diffrn_orient_matrix_UB_31      -0.0721307000
_diffrn_orient_matrix_UB_32      -0.0087593000
_diffrn_orient_matrix_UB_33      0.0087039000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3614
_diffrn_reflns_point_group_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.346
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76193
_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    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 495 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0508P)^2^+0.0351P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1409
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_full    0.686
_reflns_Friedel_fraction_max     0.685
_reflns_number_gt                1919
_reflns_number_total             2607
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09488d2.cif
_cod_data_source_block           170118_sgr4_145a
_cod_depositor_comments
'Adding full bibliography for 7121158--7121162.cif.'
_cod_original_cell_volume        1666.2(4)
_cod_database_code               7121162
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 97.47
_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.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              84864
_olex2_submission_special_instructions 'No special instructions were received'