Direct cyclopropanation of activated N-heteroarenes <i>via</i> site- and stereoselective dearomative reactions.
Lee, Jiyoun; Ko, Donguk; Park, Hyunju; Yoo, Eun Jeong; Chemical science 11 (2020) 1672–1676; doi:10.1039/c9sc06369b

data_1556994
_publ_section_title
;
 Direct cyclopropanation of activated N-heteroarenes <i>via</i> site- and
 stereoselective dearomative reactions.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1672
_journal_page_last               1676
_journal_paper_doi               10.1039/c9sc06369b
_journal_volume                  11
_journal_year                    2020
_chemical_formula_sum            'C28 H26 N2'
_chemical_formula_weight         390.51
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-07-31 deposited with the CCDC.	2020-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0720(18)
_cell_length_b                   9.846(2)
_cell_length_c                   23.918(5)
_cell_measurement_reflns_used    39160
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      33.575
_cell_measurement_theta_min      0.418
_cell_volume                     2136.4(8)
_computing_cell_refinement       HKL3000sm
_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_data_reduction        HKL3000sm
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.730
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            22591
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_theta_full        25.976
_diffrn_reflns_theta_max         33.528
_diffrn_reflns_theta_min         1.749
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'HKL3000sm Scalepack'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
_refine_ls_abs_structure_Flack    -0.2(8)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         6930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1102P)^2^+0.0310P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.1815
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                6231
_reflns_number_total             6930
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06369b2.cif
_cod_data_source_block           PO19059O_019
_cod_depositor_comments
;Adding full bibliography for 1556993--1556994.cif.

 Adding full bibliography for 1556993--1556994.cif.
;
_cod_original_cell_volume        2136.4(7)
_cod_database_code               1556994
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              35786