C–C Cleavage Approach to C–H Functionalization of Saturated Aza-Cycles
Roque, Jose B.; Kuroda, Yusuke; Jurczyk, Justin; Xu, Li-Ping; Ham, Jin Su; Göttemann, Lucas T.; Roberts, Charis A.; Adpressa, Donovon; Saurí, Josep; Joyce, Leo A.; Musaev, Djamaladdin G.; Yeung, Charles S.; Sarpong, Richmond; ACS Catalysis  (2020) 2929–2941; doi:10.1021/acscatal.9b04551

data_4517425
_publ_section_title
;
 C--C Cleavage Approach to C--H Functionalization of Saturated Aza-Cycles
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2929
_journal_page_last               2941
_journal_paper_doi               10.1021/acscatal.9b04551
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.97537(5)
_cell_length_b                   7.97537(5)
_cell_length_c                   34.7796(3)
_cell_measurement_reflns_used    19857
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.3150
_cell_measurement_theta_min      5.4840
_cell_volume                     2212.21(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            24011
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.451
_diffrn_reflns_theta_min         5.087
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.709
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 833 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0379P)^2^+0.5099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0700
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2241
_reflns_number_total             2251
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b04551_si_003.cif
_cod_data_source_block           Jurczyk001_Sarpong
_cod_depositor_comments
'Adding full bibliography for 4517425--4517427.cif.'
_cod_database_code               4517425
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.755
_shelx_estimated_absorpt_t_max   0.865
_shelx_res_checksum              5668
_shelx_hkl_checksum              11934