Palladium-Catalyzed Cascade Arene/Alkyne Annulation: Synthesis of Fluorene-Benzoxazine Derivatives.
Cai, Zhong-Jian; Li, Fang-Hui; Wang, Shun-Yi; Ji, Shun-Jun; Organic letters 18 (2016) 4810–4813; doi:10.1021/acs.orglett.6b02224

data_1555725
_publ_section_title
;
 Palladium-Catalyzed Cascade Arene/Alkyne Annulation: Synthesis of
 Fluorene-Benzoxazine Derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4810
_journal_page_last               4813
_journal_paper_doi               10.1021/acs.orglett.6b02224
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H16 F N O'
_chemical_formula_sum            'C27 H16 F N O'
_chemical_formula_weight         389.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-12
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
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_cell_length_b                   11.9086(3)
_cell_length_c                   21.8620(6)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    295.6(3)
_cell_measurement_theta_max      72.6130
_cell_measurement_theta_min      4.0310
_cell_volume                     1912.45(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.6(3)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -41.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000    0.0000 57

  2 omega  -93.00   -5.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  125.0000 -180.0000 88

  3 omega  -43.00   26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343   37.0000  120.0000 69

  4 omega   18.00   44.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2343 -125.0000 -150.0000 26

  5 omega   94.00  137.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -77.0000  120.0000 43

  6 omega   55.00   83.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000  -90.0000 28

  7 omega   82.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   45.0000  -90.0000 96

  8 omega   40.00   92.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000 -180.0000 52

  9 omega   36.00   86.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  -60.0000 50

 10 omega   32.00   58.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -30.0000  120.0000 26

 11 omega   47.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -45.0000   90.0000 50

 12 omega   26.00  108.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522  -94.0000   60.0000 82

 13 omega -114.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000  -30.0000 103

 14 omega -114.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000   60.0000 103

 15 omega -114.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2343  -57.0000 -180.0000 103

 16 omega   78.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   45.0000    0.0000 25

 17 omega   78.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      105.9522   45.0000   90.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1330197000
_diffrn_orient_matrix_UB_12      -0.0240249000
_diffrn_orient_matrix_UB_13      0.0528558000
_diffrn_orient_matrix_UB_21      0.0195250000
_diffrn_orient_matrix_UB_22      0.1222778000
_diffrn_orient_matrix_UB_23      0.0220018000
_diffrn_orient_matrix_UB_31      -0.1610322000
_diffrn_orient_matrix_UB_32      0.0347304000
_diffrn_orient_matrix_UB_33      -0.0410503000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11242
_diffrn_reflns_theta_full        67.04
_diffrn_reflns_theta_max         67.04
_diffrn_reflns_theta_min         4.04
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.781
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3366
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1552
_reflns_number_gt                2925
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02224_si_002.cif
_cod_data_source_block           g151012a
_cod_original_cell_volume        1912.46(9)
_cod_database_code               1555725
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C17(H17), C18(H18), C19(H19), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
;
_olex2_date_sample_data_collection 2015-10-12
_olex2_submission_special_instructions 'No special instructions were received'