Catalyst-free three-component sequencing for efficient assembly of [1,3] oxazine N-fused imidazole-2-thiones
Chen, En; Shao, Jiaan; Tang, Pai; Shu, Ke; Chen, Wenteng; Yu, Yongping; Green Chemistry 20 (2018) 3696–; doi:10.1039/C8GC01766B

data_7231208
_publ_section_title
;
 Catalyst-free three-component sequencing for efficient assembly of [1,3]
 oxazine N-fused imidazole-2-thiones
;
_journal_issue                   16
_journal_name_full               'Green Chemistry'
_journal_page_first              3696
_journal_paper_doi               10.1039/C8GC01766B
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 N2 O2 S'
_chemical_formula_sum            'C17 H14 N2 O2 S'
_chemical_formula_weight         310.36
_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             2017-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-08-30 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                74.013(7)
_cell_angle_beta                 72.640(9)
_cell_angle_gamma                69.444(9)
_cell_formula_units_Z            2
_cell_length_a                   8.4181(10)
_cell_length_b                   9.1433(7)
_cell_length_c                   10.4688(9)
_cell_measurement_reflns_used    1613
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5627
_cell_measurement_theta_min      3.0043
_cell_volume                     706.85(13)
_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      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -78.00    7.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -38.0000   30.0000 85

  2 omega  -37.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183   77.0000  -30.0000 92

  3 omega  -79.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -12.7183  -77.0000 -150.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0750080000
_diffrn_orient_matrix_UB_12      0.0349433000
_diffrn_orient_matrix_UB_13      -0.0279051000
_diffrn_orient_matrix_UB_21      -0.0412421000
_diffrn_orient_matrix_UB_22      0.0444521000
_diffrn_orient_matrix_UB_23      0.0529453000
_diffrn_orient_matrix_UB_31      0.0346255000
_diffrn_orient_matrix_UB_32      0.0626658000
_diffrn_orient_matrix_UB_33      -0.0405956000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4356
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.010
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95040
_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    1.458
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0492P)^2^+0.1682P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1218
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2059
_reflns_number_total             2579
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8gc01766b3.cif
_cod_data_source_block           170308_cc20170308
_cod_depositor_comments          'Adding full bibliography for 7231208.cif.'
_cod_database_code               7231208
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c10 h10 n2 o8 s1'
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.58
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              63385
_olex2_submission_special_instructions 'No special instructions were received'