Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.
Stephens, David E.; Nguyen, Vu T.; Chhetri, Bhuwan; Clark, Emily R.; Arman, Hadi D.; Larionov, Oleg V.; Organic letters 18 (2016) 5808–5811; doi:10.1021/acs.orglett.6b02719

data_1555856
_publ_section_title
;
 Organocatalytic Synthesis of Methylene-Bridged N-Heterobiaryls.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5808
_journal_page_last               5811
_journal_paper_doi               10.1021/acs.orglett.6b02719
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                91.619(4)
_cell_angle_beta                 101.145(4)
_cell_angle_gamma                98.005(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5003(3)
_cell_length_b                   8.4300(2)
_cell_length_c                   12.7367(7)
_cell_measurement_reflns_used    4643
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.1250
_cell_measurement_theta_min      1.6500
_cell_volume                     781.16(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      98.0
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5227
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.444
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0600P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4430
_reflns_number_total             5227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02719_si_002.cif
_cod_data_source_block           cd1442_twin1_hklf4
_cod_database_code               1555856
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6471(12) 0.3529(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H,H,H,H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H,H,H,H) groups
;
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'