Synergistic catalysis: cis-cyclopropanation of benzoxazoles
Meazza, Marta; Light, Mark E.; Mazzanti, Andrea; Rios, Ramon; Chem. Sci. 7 (2016) 984–; doi:10.1039/C5SC03597J

data_1540467
_publ_section_title
;
 Synergistic catalysis: cis-cyclopropanation of benzoxazoles
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              984
_journal_paper_doi               10.1039/C5SC03597J
_journal_volume                  7
_journal_year                    2016
_chemical_formula_moiety         'C17 H11 N3 O6'
_chemical_formula_sum            'C17 H11 N3 O6'
_chemical_formula_weight         353.29
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.10.02 svn.r3027 for OlexSys, GUI svn.r4900)
;
_audit_update_record
;
2015-04-20 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.161(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9877(5)
_cell_length_b                   15.1541(7)
_cell_length_c                   10.2131(6)
_cell_measurement_reflns_used    6234
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7430
_cell_measurement_theta_min      2.1410
_cell_volume                     1505.20(14)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -40.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  120.0000 108

  2 omega  -72.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000    0.0000 89

  3 omega  -78.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000 -180.0000 95

  4 omega  -67.00   15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000  -30.0000 82

  5 omega  -37.00  -10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   54.0000  -30.0000 27

  6 omega  -61.00  -51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000 -180.0000 10

  7 omega  -97.00  -73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000 -120.0000 24
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0502560000
_diffrn_orient_matrix_UB_12      0.0046371000
_diffrn_orient_matrix_UB_13      -0.0611338000
_diffrn_orient_matrix_UB_21      -0.0500267000
_diffrn_orient_matrix_UB_22      -0.0189953000
_diffrn_orient_matrix_UB_23      0.0306127000
_diffrn_orient_matrix_UB_31      -0.0169773000
_diffrn_orient_matrix_UB_32      0.0425327000
_diffrn_orient_matrix_UB_33      0.0204465000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14536
_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         28.699
_diffrn_reflns_theta_min         3.380
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_description       fragment
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.1503
_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^)+(0.0833P)^2^+11.7598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3307
_refine_ls_wR_factor_ref         0.3428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3045
_reflns_number_total             3884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc03597j2.cif
_cod_data_source_block           2014sot0046
_cod_depositor_comments          'Adding full bibliography for 1540467.cif.'
_cod_database_code               1540467
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 93.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.00
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
;
_shelx_res_checksum              67036
_shelx_hkl_checksum              63343
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id mm-7AS-60
_olex2_submission_special_instructions 'No special instructions were received'