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_4037431
_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         'C16 H20 Cl N3 O'
_chemical_formula_sum            'C16 H20 Cl N3 O'
_chemical_formula_weight         305.80
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-07
_audit_creation_method
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Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
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_cell_angle_alpha                92.525(12)
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_cell_formula_units_Z            2
_cell_length_a                   8.9790(14)
_cell_length_b                   9.3904(11)
_cell_length_c                   10.0838(16)
_cell_measurement_reflns_used    2929
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0510
_cell_measurement_theta_min      4.6480
_cell_volume                     740.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
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_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details
;
  1 omega -107.00  -29.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -61.0000 -120.0000 39

  2 omega  -69.00   33.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   77.0000    0.0000 51

  3 omega   56.00  102.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   38.0000   90.0000 23

  4 omega  -27.00   65.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573  -57.0000  120.0000 46

  5 omega   33.00   73.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -30.0000    0.0000 20

  6 omega  101.00  173.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276   77.0000   60.0000 36

  7 omega   29.00   81.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -30.0000 -180.0000 26

  8 omega   48.00  106.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -94.0000 -120.0000 29

  9 omega   29.00   91.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -30.0000   60.0000 31

 10 omega   33.00   87.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -30.0000  120.0000 27

 11 omega   46.00  120.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276 -125.0000   60.0000 37

 12 omega   50.00  106.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -94.0000  150.0000 28

 13 omega   71.00   97.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -45.0000  120.0000 13

 14 omega   38.00   84.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -94.0000  -30.0000 23

 15 omega   38.00  142.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -15.0000 -120.0000 52

 16 omega   44.00   92.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      102.6276  -77.0000   60.0000 24
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1818982000
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_diffrn_orient_matrix_UB_13      -0.0111644000
_diffrn_orient_matrix_UB_21      -0.0505034000
_diffrn_orient_matrix_UB_22      -0.0353013000
_diffrn_orient_matrix_UB_23      -0.1617849000
_diffrn_orient_matrix_UB_31      0.0554759000
_diffrn_orient_matrix_UB_32      -0.1369572000
_diffrn_orient_matrix_UB_33      0.0131081000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4796
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.712
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_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    2.299
_exptl_absorpt_correction_T_max  1.298
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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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
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_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.4734
_exptl_crystal_size_mid          0.2377
_exptl_crystal_size_min          0.1971
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0421
_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^)+(0.0666P)^2^+0.2329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2629
_reflns_number_total             2862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02315_si_004.cif
_cod_data_source_block           rljcce
_cod_database_code               4037431
_nottingham_internal_coll_name   RLJCCE
_nottingham_internal_coll_number 13000
_nottingham_internal_coll_client RL/JC
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 2
_nottingham_internal_coll_frame_width 2
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   8/11/2013
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_nottingham_internal_solution_user pczWL
_nottingham_internal_refinement_date 13/11/2013
_nottingham_internal_refinement_user pczwl
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_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 13/3/2014
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C16 H20 Cl N3 O'
_chemical_oxdiff_usercomment     'RLJCCE #13000 IN FOMBLIN FILM ON MICROMOUNT'
_reflns_odcompleteness_completeness 98.30
_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 C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(H20C)=Sof(H20D)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H20A)=Sof(H20B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,
 H18B), C18(H18C,H18D), C19(H19A,H19B), C19A(H19C,H19D), C20(H20A,H20B),
 C20(H20C,H20D), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9)
;
_shelx_res_checksum              23289
_shelx_hkl_checksum              84358
_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'