An aza-Diels–Alder approach to chlorinated quinolines, benzoquinolines, and polybenzoquinolines
Kim, Juhwan; Umerani, Mehran J.; Kurakake, Reina; Qin, Huiting; Ziller, Joseph W.; Gorodetsky, Alon A.; Park, Young S.; RSC Advances 11 (2021) 13722–13730; doi:10.1039/D0RA06744J

data_7242657
_publ_section_title
;
 An aza-Diels--Alder approach to chlorinated quinolines, benzoquinolines,
 and polybenzoquinolines
;
_journal_issue                   23
_journal_name_full               'RSC Advances'
_journal_page_first              13722
_journal_page_last               13730
_journal_paper_doi               10.1039/D0RA06744J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C10 H5 Cl I N O2'
_chemical_formula_weight         333.50
_chemical_name_systematic        2-Chloro-1-iodo-4-nitronaphthalene
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2020-08-03 deposited with the CCDC.	2021-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                102.9660(6)
_cell_angle_beta                 90.5478(7)
_cell_angle_gamma                109.4789(6)
_cell_formula_units_Z            4
_cell_length_a                   8.8632(5)
_cell_length_b                   9.5113(6)
_cell_length_c                   13.0140(8)
_cell_measurement_reflns_used    8428
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      2.34
_cell_volume                     1003.66(11)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.1-1, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2013/1'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker SMART 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  0.0138
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11841
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.703
_diffrn_reflns_theta_min         1.613
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.432
_exptl_absorpt_correction_T_max  0.7747
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS 2014/4'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Tetrahydrofuran'
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.130
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+1.4177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0614
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4304
_reflns_number_total             4701
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra06744j2.cif
_cod_data_source_block           aag8
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7242657
_shelx_estimated_absorpt_t_min   0.462
_shelx_estimated_absorpt_t_max   0.664
_shelxl_version_number           2014/6
_shelx_res_checksum              29422