Sequential annulation and isomerisation reaction of 3-acylmethylidene oxindoles with Huisgen zwitterions and synthesis of 5-(3-oxindolyl)oxazoles.
Xue, Feixue; Yang, Chang-Jiang; Tang, Tong; He, Zhengjie; Organic & biomolecular chemistry 21 (2023) 8176–8181; doi:10.1039/d3ob01199b

data_7159639
_publ_section_title
;
 Sequential annulation and isomerisation reaction of 3-acylmethylidene
 oxindoles with Huisgen zwitterions and synthesis of
 5-(3-oxindolyl)oxazoles.
;
_journal_issue                   40
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8176
_journal_page_last               8181
_journal_paper_doi               10.1039/d3ob01199b
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C29 H26 Cl N3 O5'
_chemical_formula_sum            'C29 H26 Cl N3 O5'
_chemical_formula_weight         531.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-04 deposited with the CCDC.	2023-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.880(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3512(9)
_cell_length_b                   11.2333(10)
_cell_length_c                   22.0866(18)
_cell_measurement_reflns_used    7719
_cell_measurement_temperature    113
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2567.9(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_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      113
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9555
	          2theta: -15.0863
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9555
	          2theta: -15.0863
scan:
	Number of images: 360
	           Slice: -105.0000 - 75.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9555
	          2theta: -15.0863
;
_diffrn_measurement_device
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Rigaku Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.012891
_diffrn_orient_matrix_UB_12      -0.012587
_diffrn_orient_matrix_UB_13      -0.094924
_diffrn_orient_matrix_UB_21      -0.032443
_diffrn_orient_matrix_UB_22      0.082639
_diffrn_orient_matrix_UB_23      -0.006552
_diffrn_orient_matrix_UB_31      0.041635
_diffrn_orient_matrix_UB_32      0.015676
_diffrn_orient_matrix_UB_33      -0.008441
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         3.233
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1112
_exptl_crystal_preparation       Fiber
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+0.6184P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5117
_reflns_number_total             5889
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01199b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7159639
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.962
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C25(H25A,H25B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C29(H29A,H29B,H29C)
;
_shelx_res_checksum              73609
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'