Accessing Heterobiaryls through Transition-Metal-Free C-H Functionalization.
Banik, Ananya; Paira, Rupankar; Shaw, Bikash Kumar; Vijaykumar, Gonela; Mandal, Swadhin K.; The Journal of organic chemistry 83 (2018) 3236–3244; doi:10.1021/acs.joc.8b00140

data_4035149
_publ_section_title
;
 Accessing Heterobiaryls through Transition-Metal-Free C-H
 Functionalization.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3236
_journal_page_last               3244
_journal_paper_doi               10.1021/acs.joc.8b00140
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C14 H10 N O'
_chemical_formula_sum            'C14 H10 N O'
_chemical_formula_weight         208.24
_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_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.85(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.181(6)
_cell_length_b                   4.4360(11)
_cell_length_c                   15.689(4)
_cell_measurement_reflns_used    770
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.1570
_cell_measurement_theta_min      2.6010
_cell_volume                     1052.4(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7799
_diffrn_measured_fraction_theta_max 0.7799
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -14.00  63.00   1.00  140.47    --   28.08 -99.00  30.00   77
  2  \w     68.00 108.00   1.00  140.47    --   28.08 178.00 -60.00   40
  3  \w    -25.00  82.00   1.00  140.47    --   28.08 -19.00  30.00  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0411745000
_diffrn_orient_matrix_UB_12      0.0729085000
_diffrn_orient_matrix_UB_13      -0.0097173000
_diffrn_orient_matrix_UB_21      0.0213115000
_diffrn_orient_matrix_UB_22      0.1427500000
_diffrn_orient_matrix_UB_23      0.0053560000
_diffrn_orient_matrix_UB_31      -0.0062211000
_diffrn_orient_matrix_UB_32      0.0016379000
_diffrn_orient_matrix_UB_33      -0.0472063000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_av_unetI/netI     0.1687
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3256
_diffrn_reflns_theta_full        28.3037
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.62
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3142
_exptl_crystal_description       needle
_exptl_crystal_F_000             436.1959
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.6143
_refine_diff_density_min         -0.7675
_refine_diff_density_rms         0.1670
_refine_ls_d_res_high            0.7495
_refine_ls_d_res_low             7.7708
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.7747
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     74
_refine_ls_number_reflns         2034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.7747
_refine_ls_R_factor_all          0.1802
_refine_ls_R_factor_gt           0.0887
_refine_ls_shift/su_max          0.0066
_refine_ls_shift/su_mean         0.0019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.3376
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -20
_reflns_limit_k_max              5
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                759
_reflns_number_total             2034
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00140_si_002.cif
_cod_data_source_block           Ligand1
_cod_database_code               4035149
_chemical_oxdiff_formula         'C H N'
_reflns_odcompleteness_completeness 96.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C10) = Uanis(C9) = Uanis(C8) = Uanis(C7) = Uanis(C6) =
Uanis(C5) = Uanis(C13) = Uanis(C4) = Uanis(C12) = Uanis(C3) = Uanis(C2) =
Uanis(C1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C6(H6), C3(H3), C7(H7), C5(H5), C10(H10), C2(H2)
;
_olex2_date_sample_data_collection 2016-02-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.180
_oxdiff_exptl_absorpt_empirical_full_min 0.271