Exploring the Reactivity of 2-Trichloromethylbenzoxazoles for Access to Substituted Benzoxazoles.
Lester, Roy P.; Bham, Travis; Bousfield, Thomas W.; Lewis, William; Camp, Jason E.; The Journal of organic chemistry 81 (2016) 12472–12477; doi:10.1021/acs.joc.6b02315

data_4037430
_publ_section_title
;
 Exploring the Reactivity of 2-Trichloromethylbenzoxazoles for Access to
 Substituted Benzoxazoles.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12472
_journal_page_last               12477
_journal_paper_doi               10.1021/acs.joc.6b02315
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C8 H6 Cl3 N O2'
_chemical_formula_sum            'C8 H6 Cl3 N O2'
_chemical_formula_weight         254.49
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5772(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.38358(10)
_cell_length_b                   12.1552(2)
_cell_length_c                   11.29082(16)
_cell_measurement_reflns_used    22757
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0300
_cell_measurement_theta_min      3.6510
_cell_volume                     1004.49(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_detector                 'CCD area detector'
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_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
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  2 omega    5.00   41.00   2.0000    3.0000
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  3 omega    8.00   42.00   2.0000    3.0000
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  4 omega   57.00  115.00   2.0000    3.0000
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  5 omega -106.00  -28.00   2.0000    3.0000
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  6 omega  -73.00   17.00   2.0000    3.0000
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  7 omega  -64.00  -30.00   2.0000    3.0000
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  8 omega  -54.00  -28.00   2.0000    3.0000
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  9 omega  130.00  174.00   2.0000    3.0000
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 10 omega   77.00  173.00   2.0000    3.0000
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 11 omega  124.00  150.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   77.00  137.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000   60.0000 30

 13 omega   71.00   97.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   71.00  101.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   70.00   96.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   77.00  103.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000  -60.0000 13

 17 omega   79.00  105.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   71.00  177.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega  139.00  165.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   26.00   90.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   21.00  109.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega   71.00   97.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000  -60.0000 13

 23 omega  129.00  155.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000   30.0000 13

 24 omega   77.00  171.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000  -30.0000 47

 25 omega   78.00  104.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027  125.0000  120.0000 13

 26 omega   36.00   94.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027  -45.0000 -120.0000 29

 27 omega  -50.00   38.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega    8.00  110.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 29 omega  -38.00   64.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 30 omega -140.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 31 omega -139.00  -29.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 32 omega -140.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 33 omega  -56.00   12.00   2.0000    3.0000
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 34 omega -140.00  -28.00   2.0000    3.0000
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 35 omega   77.00  177.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 36 omega   29.00   99.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027  -45.0000  150.0000 35

 37 omega   29.00  121.00   2.0000    3.0000
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 38 omega   70.00  178.00   2.0000    3.0000
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 39 omega   70.00  178.00   2.0000    3.0000
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 40 omega   77.00  177.00   2.0000    3.0000
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    -      104.1027   45.0000  120.0000 50

 41 omega   74.00  178.00   2.0000    3.0000
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 42 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 43 omega   20.00  108.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 44 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000 -150.0000 54

 45 omega    4.00  116.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5322   77.0000   90.0000 56

 46 omega    4.00  116.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5322   77.0000    0.0000 56

 47 omega    4.00  116.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5322   77.0000 -150.0000 56

 48 omega -136.00  -74.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega -140.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega -140.00  -28.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000 -150.0000 52

 53 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000 -120.0000 54

 54 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000  120.0000 52

 55 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000   30.0000 54

 56 omega   20.00  108.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027  -94.0000  -30.0000 44

 57 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000 -180.0000 52

 58 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000  150.0000 54

 59 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000   90.0000 54

 60 omega   25.00  137.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027  -77.0000  120.0000 56

 61 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   61.0000 -120.0000 52

 62 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000 -180.0000 54

 63 omega  -52.00  126.00   2.0000    3.0000
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 64 omega  -52.00  126.00   2.0000    3.0000
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 65 omega  -52.00  126.00   2.0000    3.0000
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 66 omega   74.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 67 omega   20.00  108.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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 68 omega   70.00  178.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      104.1027   77.0000  -30.0000 54
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1754192000
_diffrn_orient_matrix_UB_12      -0.0323536000
_diffrn_orient_matrix_UB_13      -0.0517638000
_diffrn_orient_matrix_UB_21      0.1097790000
_diffrn_orient_matrix_UB_22      0.0088914000
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_diffrn_orient_matrix_UB_31      -0.0384318000
_diffrn_orient_matrix_UB_32      -0.1222169000
_diffrn_orient_matrix_UB_33      0.0228349000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34200
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.089
_diffrn_reflns_theta_min         5.373
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    8.054
_exptl_absorpt_correction_T_max  0.622
_exptl_absorpt_correction_T_min  0.156
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3282
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.1086
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2035
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0369P)^2^+0.4645P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1986
_reflns_number_total             2035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02315_si_002.cif
_cod_data_source_block           rljccb
_cod_database_code               4037430
_nottingham_internal_coll_name   RLJCCB
_nottingham_internal_coll_number 12874
_nottingham_internal_coll_client RL/JC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 3
_nottingham_internal_coll_frame_width 2
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   02/10/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 03/10/2013
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 3/10/2013
_nottingham_internal_solution_user WL
_nottingham_internal_refinement_date 3/10/2013
_nottingham_internal_refinement_user wl
_nottingham_internal_validation_date 7/9/2016
_nottingham_internal_validation_user wl
_nottingham_internal_archive_date 13/3/2014
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C8 H6 Cl3 N O2'
_chemical_oxdiff_usercomment
'RLJCCB #12874 IN FOMBLIN FIML ON MICROMOUNT FOR RL/JC'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
;
_shelx_res_checksum              3294
_shelx_hkl_checksum              36927
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method 'mounted in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'