#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:35:05 +0200 (Sat 23 de Aug de 2025) $
#$Revision: 301870 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/26/7242657.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7242657
loop_
_publ_author_name
'Kim, Juhwan'
'Umerani, Mehran J.'
'Kurakake, Reina'
'Qin, Huiting'
'Ziller, Joseph W.'
'Gorodetsky, Alon A.'
'Park, Young S.'
_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       'φ and ω 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/[σ²(Fo²)+(0.0313P)²+1.4177P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.462
_shelx_estimated_absorpt_t_max   0.664
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.28981(2) 0.54578(2) 0.47332(2) 0.02084(6) Uani 1 1 d . . . . .
Cl1 Cl 0.51527(8) 0.52028(7) 0.26838(5) 0.02181(14) Uani 1 1 d . . . . .
O1 O 0.5836(3) 0.9879(3) 0.11161(16) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.6055(3) 1.1762(2) 0.24574(17) 0.0287(5) Uani 1 1 d . . . . .
N1 N 0.5646(3) 1.0411(3) 0.20311(16) 0.0162(4) Uani 1 1 d . . . . .
C1 C 0.4911(3) 0.9271(3) 0.2671(2) 0.0159(5) Uani 1 1 d . . . . .
C2 C 0.5265(3) 0.7953(3) 0.2435(2) 0.0171(5) Uani 1 1 d . . . . .
H2A H 0.5902 0.7775 0.1871 0.021 Uiso 1 1 calc R U . . .
C3 C 0.4677(3) 0.6859(3) 0.3034(2) 0.0171(5) Uani 1 1 d . . . . .
C4 C 0.3769(3) 0.7099(3) 0.3854(2) 0.0156(5) Uani 1 1 d . . . . .
C5 C 0.3382(3) 0.8481(3) 0.41097(19) 0.0138(5) Uani 1 1 d . . . . .
C6 C 0.2448(3) 0.8789(3) 0.4956(2) 0.0177(5) Uani 1 1 d . . . . .
H6A H 0.2097 0.8081 0.5389 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2042(3) 1.0093(3) 0.5158(2) 0.0207(5) Uani 1 1 d . . . . .
H7A H 0.1434 1.0289 0.5735 0.025 Uiso 1 1 calc R U . . .
C8 C 0.2521(3) 1.1124(3) 0.4519(2) 0.0203(5) Uani 1 1 d . . . . .
H8A H 0.2196 1.2000 0.4656 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3439(3) 1.0927(3) 0.3704(2) 0.0182(5) Uani 1 1 d . . . . .
H9A H 0.3746 1.1650 0.3278 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3941(3) 0.9596(3) 0.34942(19) 0.0139(5) Uani 1 1 d . . . . .
I2 I -0.22482(2) 0.81214(2) 0.95297(2) 0.02473(6) Uani 1 1 d . . . . .
Cl2 Cl 0.01366(9) 0.84491(8) 0.75476(6) 0.02507(15) Uani 1 1 d . . . . .
O3 O 0.0977(3) 0.3304(2) 0.61968(16) 0.0258(4) Uani 1 1 d . . . . .
O4 O 0.1143(3) 0.2407(3) 0.75581(18) 0.0305(5) Uani 1 1 d . . . . .
N2 N 0.0753(3) 0.3240(3) 0.71170(18) 0.0177(4) Uani 1 1 d . . . . .
C11 C -0.0001(3) 0.4314(3) 0.7718(2) 0.0156(5) Uani 1 1 d . . . . .
C12 C 0.0309(3) 0.5662(3) 0.7418(2) 0.0177(5) Uani 1 1 d . . . . .
H12A H 0.0955 0.5857 0.6853 0.021 Uiso 1 1 calc R U . . .
C13 C -0.0330(3) 0.6757(3) 0.7950(2) 0.0178(5) Uani 1 1 d . . . . .
C14 C -0.1294(3) 0.6476(3) 0.8750(2) 0.0172(5) Uani 1 1 d . . . . .
C15 C -0.1649(3) 0.5060(3) 0.9073(2) 0.0149(5) Uani 1 1 d . . . . .
C16 C -0.2647(3) 0.4722(3) 0.9894(2) 0.0195(5) Uani 1 1 d . . . . .
H16A H -0.3125 0.5439 1.0236 0.023 Uiso 1 1 calc R U . . .
C17 C -0.2935(3) 0.3379(3) 1.0202(2) 0.0214(6) Uani 1 1 d . . . . .
H17A H -0.3584 0.3187 1.0767 0.026 Uiso 1 1 calc R U . . .
C18 C -0.2289(3) 0.2298(3) 0.9700(2) 0.0195(5) Uani 1 1 d . . . . .
H18A H -0.2508 0.1371 0.9924 0.023 Uiso 1 1 calc R U . . .
C19 C -0.1335(3) 0.2537(3) 0.8882(2) 0.0169(5) Uani 1 1 d . . . . .
H19A H -0.0919 0.1772 0.8538 0.020 Uiso 1 1 calc R U . . .
C20 C -0.0974(3) 0.3940(3) 0.8553(2) 0.0146(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 125.3(2) . . ?
O2 N1 C1 118.5(2) . . ?
O1 N1 C1 116.1(2) . . ?
C2 C1 C10 123.1(2) . . ?
C2 C1 N1 116.1(2) . . ?
C10 C1 N1 120.8(2) . . ?
C1 C2 C3 119.3(2) . . ?
C4 C3 C2 121.2(2) . . ?
C4 C3 Cl1 121.8(2) . . ?
C2 C3 Cl1 117.0(2) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 I1 120.71(19) . . ?
C5 C4 I1 119.18(18) . . ?
C6 C5 C10 118.1(2) . . ?
C6 C5 C4 122.3(2) . . ?
C10 C5 C4 119.5(2) . . ?
C7 C6 C5 121.1(2) . . ?
C6 C7 C8 120.1(2) . . ?
C9 C8 C7 122.4(3) . . ?
C8 C9 C10 118.9(2) . . ?
C1 C10 C5 116.7(2) . . ?
C1 C10 C9 124.1(2) . . ?
C5 C10 C9 119.1(2) . . ?
O4 N2 O3 124.5(2) . . ?
O4 N2 C11 119.3(2) . . ?
O3 N2 C11 116.3(2) . . ?
C12 C11 C20 123.1(2) . . ?
C12 C11 N2 115.5(2) . . ?
C20 C11 N2 121.4(2) . . ?
C11 C12 C13 119.6(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 Cl2 121.9(2) . . ?
C12 C13 Cl2 117.3(2) . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 I2 120.2(2) . . ?
C15 C14 I2 119.14(19) . . ?
C16 C15 C20 118.3(2) . . ?
C16 C15 C14 122.4(2) . . ?
C20 C15 C14 119.3(2) . . ?
C17 C16 C15 121.1(3) . . ?
C16 C17 C18 120.7(3) . . ?
C19 C18 C17 121.4(3) . . ?
C18 C19 C20 119.7(3) . . ?
C19 C20 C11 124.7(2) . . ?
C19 C20 C15 118.8(2) . . ?
C11 C20 C15 116.5(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C4 2.087(2) . ?
Cl1 C3 1.729(3) . ?
O1 N1 1.222(3) . ?
O2 N1 1.206(3) . ?
N1 C1 1.496(3) . ?
C1 C2 1.362(4) . ?
C1 C10 1.425(3) . ?
C2 C3 1.404(4) . ?
C3 C4 1.367(4) . ?
C4 C5 1.436(3) . ?
C5 C6 1.420(3) . ?
C5 C10 1.432(3) . ?
C6 C7 1.375(4) . ?
C7 C8 1.389(4) . ?
C8 C9 1.361(4) . ?
C9 C10 1.449(4) . ?
I2 C14 2.093(3) . ?
Cl2 C13 1.724(3) . ?
O3 N2 1.227(3) . ?
O4 N2 1.209(3) . ?
N2 C11 1.485(3) . ?
C11 C12 1.365(4) . ?
C11 C20 1.429(3) . ?
C12 C13 1.400(4) . ?
C13 C14 1.369(4) . ?
C14 C15 1.437(4) . ?
C15 C16 1.418(4) . ?
C15 C20 1.435(4) . ?
C16 C17 1.368(4) . ?
C17 C18 1.381(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.428(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C2 -144.9(3) . . . . ?
O1 N1 C1 C2 32.4(3) . . . . ?
O2 N1 C1 C10 33.4(4) . . . . ?
O1 N1 C1 C10 -149.3(2) . . . . ?
C10 C1 C2 C3 -1.0(4) . . . . ?
N1 C1 C2 C3 177.2(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C2 C3 Cl1 179.4(2) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
Cl1 C3 C4 C5 -179.14(19) . . . . ?
C2 C3 C4 I1 179.80(19) . . . . ?
Cl1 C3 C4 I1 -0.1(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
I1 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C5 C10 0.5(4) . . . . ?
I1 C4 C5 C10 -178.48(18) . . . . ?
C10 C5 C6 C7 2.2(4) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C6 C7 C8 C9 -2.2(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C2 C1 C10 C5 2.3(4) . . . . ?
N1 C1 C10 C5 -175.8(2) . . . . ?
C2 C1 C10 C9 -174.7(2) . . . . ?
N1 C1 C10 C9 7.2(4) . . . . ?
C6 C5 C10 C1 178.3(2) . . . . ?
C4 C5 C10 C1 -2.0(3) . . . . ?
C6 C5 C10 C9 -4.5(3) . . . . ?
C4 C5 C10 C9 175.1(2) . . . . ?
C8 C9 C10 C1 -179.5(2) . . . . ?
C8 C9 C10 C5 3.6(4) . . . . ?
O4 N2 C11 C12 148.5(3) . . . . ?
O3 N2 C11 C12 -29.4(3) . . . . ?
O4 N2 C11 C20 -31.1(4) . . . . ?
O3 N2 C11 C20 150.9(2) . . . . ?
C20 C11 C12 C13 0.6(4) . . . . ?
N2 C11 C12 C13 -179.0(2) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C11 C12 C13 Cl2 178.9(2) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
Cl2 C13 C14 C15 -179.4(2) . . . . ?
C12 C13 C14 I2 -179.67(19) . . . . ?
Cl2 C13 C14 I2 -0.2(3) . . . . ?
C13 C14 C15 C16 -179.7(3) . . . . ?
I2 C14 C15 C16 1.0(3) . . . . ?
C13 C14 C15 C20 0.4(4) . . . . ?
I2 C14 C15 C20 -178.92(18) . . . . ?
C20 C15 C16 C17 1.5(4) . . . . ?
C14 C15 C16 C17 -178.5(3) . . . . ?
C15 C16 C17 C18 -1.7(4) . . . . ?
C16 C17 C18 C19 0.3(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C11 180.0(2) . . . . ?
C18 C19 C20 C15 -1.3(4) . . . . ?
C12 C11 C20 C19 179.5(3) . . . . ?
N2 C11 C20 C19 -0.9(4) . . . . ?
C12 C11 C20 C15 0.8(4) . . . . ?
N2 C11 C20 C15 -179.6(2) . . . . ?
C16 C15 C20 C19 0.0(4) . . . . ?
C14 C15 C20 C19 180.0(2) . . . . ?
C16 C15 C20 C11 178.8(2) . . . . ?
C14 C15 C20 C11 -1.2(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342135
