A practical route to arylated dihydroacridine derivatives via nickel boride mediated intramolecular reductive cyclization-concomitant dehydration
Sarkar, Rumpa; Samanta, Surya Kanta; Hasija, Avantika; Chopra, Deepak; Ganguly, Debabani; Bera, Mrinal K.; New Journal of Chemistry 46 (2022) 7168–7176; doi:10.1039/D1NJ05196B

data_7061383
_publ_section_title
;
 A practical route to arylated dihydroacridine derivatives via nickel
 boride mediated intramolecular reductive cyclization-concomitant
 dehydration
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7168
_journal_page_last               7176
_journal_paper_doi               10.1039/D1NJ05196B
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-11-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-07 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.293(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5986(13)
_cell_length_b                   6.1021(10)
_cell_length_c                   14.110(2)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.90
_cell_volume                     650.30(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.697
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_coef       0.040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     1057
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0636
_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^)+(0.0168P)^2^+0.1633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2007
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj05196b2.cif
_cod_data_source_block           mkb_7
_cod_depositor_comments
'Adding full bibliography for 7061383--7061384.cif.'
_cod_database_code               7061383
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.006 and sigma
for terminal atoms of 0.008 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(N1B)=Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(C10B)=
 Sof(H10B)=Sof(C11B)=Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13C)=
 Sof(H13D)=Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=1-FVAR(1)
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=
 Sof(H13B)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C13A(H13A,H13B), C12B(H12C,H12D), C13B(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C2B(H2B), C3B(H3B), C4B(H4B),
 C5B(H5B), C7B(H7B), C10B(H10B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B),
  C19B(H19B)
;
_shelx_res_checksum              68500
_olex2_submission_special_instructions 'No special instructions were received'