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#$Date: 2022-02-22 12:35:21 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104601.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_8104601
loop_
_publ_author_name
'Deng, Zu-Shuai'
'Luo, Peng'
'Pan, Wei-Gao'
_publ_section_title
;
 Crystal structure of 2-chloro-3-(isopentylamino)naphthalene-1,4-dione, C
 15 H 16 ClNO 2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1337
_journal_page_last               1339
_journal_paper_doi               10.1515/ncrs-2021-0333
_journal_volume                  236
_journal_year                    2021
_chemical_formula_sum            'C15 H16 Cl N O2'
_chemical_formula_weight         277.74
_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   mixed
_cell_angle_alpha                108.804(6)
_cell_angle_beta                 93.672(5)
_cell_angle_gamma                94.373(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4339(12)
_cell_length_b                   8.2564(14)
_cell_length_c                   12.184(2)
_cell_measurement_reflns_used    5640
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      3.14
_cell_volume                     702.7(2)
_computing_cell_refinement       'Bruker SAINT[1]'
_computing_data_collection       'Bruker APEX3[1]'
_computing_data_reduction        'Bruker SAINT[1]'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2008)[2]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)[3]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)[2]'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14672
_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         27.549
_diffrn_reflns_theta_min         3.138
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9720
_exptl_absorpt_correction_T_min  0.8831
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3219
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0650
_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/[σ²(Fo²)+(0.1212P)²+0.0904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1974
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2111
_reflns_number_total             3219
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0333_suppl.cif
_cod_data_source_block           44
_cod_original_cell_volume        702.8(2)
_cod_database_code               8104601
_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   0.883
_shelx_estimated_absorpt_t_max   0.972
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
C1 C 0.2951(3) 0.2482(3) 0.9100(2) 0.0498(6) Uani 1 1 d . . . . .
C2 C 0.4437(3) 0.3022(3) 0.85496(19) 0.0438(6) Uani 1 1 d . . . . .
C3 C 0.6218(3) 0.3226(3) 0.89986(18) 0.0407(5) Uani 1 1 d . . . . .
C4 C 0.6629(3) 0.2939(3) 1.0150(2) 0.0452(6) Uani 1 1 d . . . . .
C5 C 0.5144(3) 0.2296(3) 1.0696(2) 0.0458(6) Uani 1 1 d . . . . .
C6 C 0.5497(4) 0.1871(3) 1.1697(2) 0.0588(7) Uani 1 1 d . . . . .
H6 H 0.6681 0.2009 1.2034 0.071 Uiso 1 1 calc R U . . .
C7 C 0.4107(5) 0.1247(4) 1.2195(2) 0.0668(8) Uani 1 1 d . . . . .
H7 H 0.4355 0.0952 1.2860 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2352(4) 0.1062(3) 1.1705(3) 0.0663(8) Uani 1 1 d . . . . .
H8 H 0.1415 0.0636 1.2038 0.080 Uiso 1 1 calc R U . . .
C9 C 0.1975(4) 0.1506(3) 1.0722(2) 0.0570(7) Uani 1 1 d . . . . .
H9 H 0.0781 0.1406 1.0409 0.068 Uiso 1 1 calc R U . . .
C10 C 0.3365(3) 0.2101(3) 1.0195(2) 0.0450(6) Uani 1 1 d . . . . .
C11 C 0.8048(3) 0.4157(3) 0.7568(2) 0.0500(6) Uani 1 1 d . . . . .
H11A H 0.9129 0.4966 0.7747 0.060 Uiso 1 1 calc R U . . .
H11B H 0.7037 0.4747 0.7403 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8273(4) 0.2676(3) 0.6491(2) 0.0546(6) Uani 1 1 d . . . . .
H12A H 0.7180 0.1881 0.6293 0.066 Uiso 1 1 calc R U . . .
H12B H 0.9267 0.2067 0.6656 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8649(4) 0.3257(4) 0.5453(2) 0.0663(8) Uani 1 1 d . . . . .
H13 H 0.9667 0.4161 0.5710 0.080 Uiso 1 1 calc R U . . .
C14 C 0.7050(6) 0.4038(5) 0.5061(3) 0.0935(11) Uani 1 1 d . . . . .
H14A H 0.5996 0.3217 0.4868 0.140 Uiso 1 1 calc R U . . .
H14B H 0.7317 0.4344 0.4388 0.140 Uiso 1 1 calc R U . . .
H14C H 0.6825 0.5048 0.5677 0.140 Uiso 1 1 calc R U . . .
C15 C 0.9208(7) 0.1841(6) 0.4459(3) 0.1187(17) Uani 1 1 d . . . . .
H15A H 0.9412 0.2256 0.3823 0.178 Uiso 1 1 calc R U . . .
H15B H 0.8267 0.0901 0.4215 0.178 Uiso 1 1 calc R U . . .
H15C H 1.0304 0.1455 0.4702 0.178 Uiso 1 1 calc R U . . .
Cl1 Cl 0.37878(9) 0.32735(10) 0.72237(5) 0.0664(3) Uani 1 1 d . . . . .
N1 N 0.7733(3) 0.3660(3) 0.85855(18) 0.0520(6) Uani 1 1 d . . . . .
O1 O 0.1372(2) 0.2296(3) 0.86772(18) 0.0747(6) Uani 1 1 d . . . . .
O2 O 0.8179(2) 0.3235(3) 1.05979(15) 0.0646(5) Uani 1 1 d . . . . .
H16 H 0.860(4) 0.359(4) 0.899(3) 0.061(8) Uiso 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'
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
O1 C1 C2 122.0(2) . .
O1 C1 C10 119.6(2) . .
C2 C1 C10 118.4(2) . .
C3 C2 C1 123.2(2) . .
C3 C2 Cl1 122.86(19) . .
C1 C2 Cl1 113.80(17) . .
N1 C3 C2 130.6(2) . .
N1 C3 C4 111.09(19) . .
C2 C3 C4 118.3(2) . .
O2 C4 C5 121.7(2) . .
O2 C4 C3 119.1(2) . .
C5 C4 C3 119.27(19) . .
C6 C5 C10 119.7(2) . .
C6 C5 C4 120.8(2) . .
C10 C5 C4 119.5(2) . .
C7 C6 C5 120.6(3) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C8 C7 C6 119.7(3) . .
C8 C7 H7 120.1 . .
C6 C7 H7 120.1 . .
C7 C8 C9 120.4(3) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C10 120.5(3) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C5 119.0(2) . .
C9 C10 C1 120.0(2) . .
C5 C10 C1 121.0(2) . .
N1 C11 C12 114.2(2) . .
N1 C11 H11A 108.7 . .
C12 C11 H11A 108.7 . .
N1 C11 H11B 108.7 . .
C12 C11 H11B 108.7 . .
H11A C11 H11B 107.6 . .
C11 C12 C13 112.5(2) . .
C11 C12 H12A 109.1 . .
C13 C12 H12A 109.1 . .
C11 C12 H12B 109.1 . .
C13 C12 H12B 109.1 . .
H12A C12 H12B 107.8 . .
C15 C13 C14 110.8(3) . .
C15 C13 C12 112.2(3) . .
C14 C13 C12 111.9(3) . .
C15 C13 H13 107.2 . .
C14 C13 H13 107.2 . .
C12 C13 H13 107.2 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C3 N1 C11 132.1(2) . .
C3 N1 H16 110(2) . .
C11 N1 H16 118(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.229(3) .
C1 C2 1.443(4) .
C1 C10 1.486(3) .
C2 C3 1.376(3) .
C2 Cl1 1.737(2) .
C3 N1 1.333(3) .
C3 C4 1.513(3) .
C4 O2 1.215(3) .
C4 C5 1.476(3) .
C5 C6 1.388(4) .
C5 C10 1.396(3) .
C6 C7 1.379(4) .
C6 H6 0.9300 .
C7 C8 1.376(4) .
C7 H7 0.9300 .
C8 C9 1.379(4) .
C8 H8 0.9300 .
C9 C10 1.390(4) .
C9 H9 0.9300 .
C11 N1 1.453(3) .
C11 C12 1.507(4) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.525(4) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C15 1.494(5) .
C13 C14 1.517(4) .
C13 H13 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
N1 H16 0.80(3) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B Cl1 0.97 2.58 3.165(3) 118.6 .
C12 H12A Cl1 0.97 2.99 3.536(3) 117.0 .
N1 H16 O2 0.80(3) 2.11(3) 2.591(3) 118(3) .
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
O1 C1 C2 C3 -179.5(2) . . . .
C10 C1 C2 C3 -1.0(3) . . . .
O1 C1 C2 Cl1 -2.9(3) . . . .
C10 C1 C2 Cl1 175.53(16) . . . .
C1 C2 C3 N1 177.7(2) . . . .
Cl1 C2 C3 N1 1.5(4) . . . .
C1 C2 C3 C4 -2.5(3) . . . .
Cl1 C2 C3 C4 -178.75(15) . . . .
N1 C3 C4 O2 5.1(3) . . . .
C2 C3 C4 O2 -174.8(2) . . . .
N1 C3 C4 C5 -174.5(2) . . . .
C2 C3 C4 C5 5.7(3) . . . .
O2 C4 C5 C6 -5.4(4) . . . .
C3 C4 C5 C6 174.2(2) . . . .
O2 C4 C5 C10 175.1(2) . . . .
C3 C4 C5 C10 -5.4(3) . . . .
C10 C5 C6 C7 0.5(4) . . . .
C4 C5 C6 C7 -179.1(2) . . . .
C5 C6 C7 C8 -0.8(4) . . . .
C6 C7 C8 C9 -0.3(4) . . . .
C7 C8 C9 C10 1.7(4) . . . .
C8 C9 C10 C5 -2.0(4) . . . .
C8 C9 C10 C1 176.6(2) . . . .
C6 C5 C10 C9 0.9(3) . . . .
C4 C5 C10 C9 -179.5(2) . . . .
C6 C5 C10 C1 -177.7(2) . . . .
C4 C5 C10 C1 1.8(3) . . . .
O1 C1 C10 C9 1.3(4) . . . .
C2 C1 C10 C9 -177.2(2) . . . .
O1 C1 C10 C5 179.9(2) . . . .
C2 C1 C10 C5 1.4(3) . . . .
N1 C11 C12 C13 -178.5(2) . . . .
C11 C12 C13 C15 169.4(3) . . . .
C11 C12 C13 C14 -65.4(4) . . . .
C2 C3 N1 C11 4.0(4) . . . .
C4 C3 N1 C11 -175.8(2) . . . .
C12 C11 N1 C3 -90.5(3) . . . .
