Transition metal-free direct dehydrogenative arylation of activated C(sp<sup>3</sup>)-H bonds: synthetic ambit and DFT reactivity predictions.
Lovato, Kaitlyn; Guo, Lirong; Xu, Qing-Long; Liu, Fengting; Yousufuddin, Muhammed; Ess, Daniel H.; Kürti, László; Gao, Hongyin; Chemical science 9 (2018) 7992–7999; doi:10.1039/c8sc02758g

data_1549853
_publ_section_title
;
 Transition metal-free direct dehydrogenative arylation of activated
 C(sp<sup>3</sup>)-H bonds: synthetic ambit and DFT reactivity
 predictions.
;
_journal_issue                   41
_journal_name_full               'Chemical science'
_journal_page_first              7992
_journal_page_last               7999
_journal_paper_doi               10.1039/c8sc02758g
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C19 H15 Br N2 O3'
_chemical_formula_sum            'C19 H15 Br N2 O3'
_chemical_formula_weight         399.24
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2018-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.054(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.499(3)
_cell_length_b                   20.581(6)
_cell_length_c                   8.367(2)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.27
_cell_volume                     1718.9(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15229
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.977
_exptl_absorpt_coefficient_mu    2.412
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0500 after correction.
The Ratio of minimum to maximum transmission is 0.8413.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0262P)^2^+0.8078P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2031
_reflns_number_total             3039
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02758g3.cif
_cod_data_source_block           p
_cod_depositor_comments
'Adding full bibliography for 1549853--1549854.cif.'
_cod_database_code               1549853
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.714
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'