A sequential Friedländer and anionic benzannulation strategy for the regiodefined assembly of unsymmetrical acridines.
Bhatta, Suman; Senapati, Bidyut Kumar; Patra, Sanjib Kumar; Nanda, Samik; Organic & biomolecular chemistry 21 (2023) 8727–8738; doi:10.1039/d3ob01470c

data_7159595
_publ_section_title
;
 A sequential Friedl&#xe4;nder and anionic benzannulation strategy for the
 regiodefined assembly of unsymmetrical acridines.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8727
_journal_page_last               8738
_journal_paper_doi               10.1039/d3ob01470c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H15 Br N2 O5'
_chemical_formula_sum            'C22 H15 Br N2 O5'
_chemical_formula_weight         467.27
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-03-12 deposited with the CCDC.	2023-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0568(9)
_cell_length_b                   10.5478(11)
_cell_length_c                   23.068(3)
_cell_measurement_reflns_used    5772
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.14
_cell_measurement_theta_min      2.53
_cell_volume                     1960.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41669
_diffrn_reflns_theta_full        26.84
_diffrn_reflns_theta_max         26.84
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    2.135
_exptl_absorpt_correction_T_max  0.7401
_exptl_absorpt_correction_T_min  0.6747
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.351(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0634P)^2^+2.7386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1592
_reflns_number_gt                3235
_reflns_number_total             4204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3ob01470c2.cif
_cod_data_source_block           SNSB258
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159594--7159598.cif.

2025-01-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         373.82
_cod_original_formula_moiety         'C17.60 H12 Br0.80 N1.60 O4'
_cod_original_formula_units_Z            5
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_original_formula_sum        'C17.60 H12 Br0.80 N1.60 O4'
_cod_database_code               7159595