Superbase-promoted selective carbon-carbon bond cleavage driven by aromatization.
Liu, Can; Zhu, Xianjin; Han, Yongzhen; Yang, Haijun; Zhu, Changjin; Fu, Hua; Organic & biomolecular chemistry 17 (2019) 4984–4989; doi:10.1039/c9ob00606k

data_7156818
_publ_section_title
;
 Superbase-promoted selective carbon-carbon bond cleavage driven by
 aromatization.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4984
_journal_page_last               4989
_journal_paper_doi               10.1039/c9ob00606k
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C22 H16 N2'
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9103(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.84497(9)
_cell_length_b                   20.0214(4)
_cell_length_c                   15.7697(3)
_cell_measurement_reflns_used    3591
_cell_measurement_temperature    108.9(7)
_cell_measurement_theta_max      71.1640
_cell_measurement_theta_min      3.5670
_cell_volume                     1518.60(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.9(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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   -113.00 -16.00   1.00    2.00    --  -40.81 -38.00-120.00   97
  2  \w   -103.00 -16.00   1.00    2.00    --  -40.81 -38.00 -30.00   87
  3  \w    -69.00 -10.00   1.00    2.00    --  -40.81 125.00 120.00   59
  4  \w     23.00  95.00   1.00    2.00    --   40.81-125.00 150.00   72
  5  \w     65.00  95.00   1.00    4.00    --  100.91-125.00-180.00   30
  6  \w     30.00 109.00   1.00    4.00    --  100.91 -95.00-180.00   79
  7  \w     86.00 112.00   1.00    4.00    --  100.91  61.00 -30.00   26
  8  \w     29.00  83.00   1.00    4.00    --  100.91-125.00   0.00   54
  9  \w     19.00 127.00   1.00    4.00    --  100.91 -15.00 -30.00  108
 10  \w     87.00 113.00   1.00    4.00    --  100.91-125.00   0.00   26
 11  \w     31.00 119.00   1.00    4.00    --  100.91 -45.00-180.00   88
 12  \w    134.00 173.00   1.00    4.00    --  100.91  61.00 -30.00   39
 13  \w     84.00 170.00   1.00    4.00    --  100.91  30.00 150.00   86
 14  \w     26.00 132.00   1.00    4.00    --  100.91 -77.00   0.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494840000
_diffrn_orient_matrix_UB_12      0.0167636000
_diffrn_orient_matrix_UB_13      -0.0960252000
_diffrn_orient_matrix_UB_21      -0.0408966000
_diffrn_orient_matrix_UB_22      -0.0747472000
_diffrn_orient_matrix_UB_23      -0.0209800000
_diffrn_orient_matrix_UB_31      -0.3136739000
_diffrn_orient_matrix_UB_32      0.0071174000
_diffrn_orient_matrix_UB_33      0.0057805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.294
_diffrn_reflns_theta_min         3.584
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0511P)^2^+0.4911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2451
_reflns_number_total             2899
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00606k2.cif
_cod_data_source_block           20190107liucan
_cod_depositor_comments          'Adding full bibliography for 7156818.cif.'
_cod_database_code               7156818
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              43995
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.563