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#$Date: 2022-04-06 11:19:37 +0300 (Wed, 06 Apr 2022) $
#$Revision: 274377 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105042.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_8105042
loop_
_publ_author_name
'Liu, Peilian'
'Jiang, Fangru'
'Huang, Guiyuan'
'Sun, Ying'
'Huang, Liping'
_publ_section_title
;
 Crystal structure of
 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              147
_journal_page_last               149
_journal_paper_doi               10.1515/ncrs-2019-0548
_journal_volume                  235
_journal_year                    2019
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 127.0225(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.5693(13)
_cell_length_b                   8.3005(4)
_cell_length_c                   16.8797(8)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.02
_cell_volume                     3084.0(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker 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  0.0298
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31095
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         3.023
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0918 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.9152.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0642
_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)+(0.1300P)²+2.1670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2057
_refine_ls_wR_factor_ref         0.2248
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2671
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0548_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105042
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C18, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C18 \\sim C17: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C15(H15A,H15B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C9(H9), C11(H11), C4(H4), C10(H10)
4.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
O1 O 0.30031(7) 0.6297(2) 0.30484(11) 0.0686(5) Uani 1 1 d . . . . .
O2 O 0.45605(7) 0.8653(2) 0.32676(11) 0.0647(5) Uani 1 1 d . . . . .
N1 N 0.22534(7) 0.4389(2) -0.12224(12) 0.0474(4) Uani 1 1 d . . . . .
H1 H 0.243974 0.462069 -0.147217 0.057 Uiso 1 1 calc R . . . .
N2 N 0.37735(7) 0.7497(2) 0.31439(11) 0.0479(4) Uani 1 1 d . . . . .
C8 C 0.30429(8) 0.5873(2) 0.02425(13) 0.0380(4) Uani 1 1 d . . . . .
C7 C 0.32833(7) 0.6424(2) 0.12118(12) 0.0365(4) Uani 1 1 d . . . . .
C14 C 0.32363(9) 0.6604(3) 0.26366(14) 0.0477(5) Uani 1 1 d . . . . .
C3 C 0.24894(8) 0.4942(2) -0.03004(13) 0.0402(4) Uani 1 1 d . . . . .
C6 C 0.29836(8) 0.6073(2) 0.16359(13) 0.0408(4) Uani 1 1 d . . . . .
C12 C 0.38248(8) 0.7334(2) 0.17485(13) 0.0409(4) Uani 1 1 d . . . . .
C5 C 0.24489(9) 0.5204(2) 0.10866(15) 0.0468(5) Uani 1 1 d . . . . .
H5 H 0.224728 0.498626 0.136053 0.056 Uiso 1 1 calc R . . . .
C9 C 0.33562(9) 0.6288(2) -0.01509(14) 0.0459(5) Uani 1 1 d . . . . .
H9 H 0.320540 0.594598 -0.078555 0.055 Uiso 1 1 calc R . . . .
C11 C 0.41153(9) 0.7712(3) 0.13367(15) 0.0484(5) Uani 1 1 d . . . . .
H11 H 0.447037 0.831904 0.169437 0.058 Uiso 1 1 calc R . . . .
C2 C 0.17041(9) 0.3427(2) -0.18122(15) 0.0497(5) Uani 1 1 d . . . . .
H2A H 0.136607 0.402436 -0.192208 0.060 Uiso 1 1 calc R . . . .
H2B H 0.175468 0.244614 -0.145707 0.060 Uiso 1 1 calc R . . . .
C13 C 0.40872(9) 0.7890(2) 0.27621(14) 0.0466(5) Uani 1 1 d . . . . .
C4 C 0.22038(8) 0.4649(2) 0.01444(15) 0.0460(5) Uani 1 1 d . . . . .
H4 H 0.184224 0.406976 -0.020090 0.055 Uiso 1 1 calc R . . . .
C16 C 0.44929(10) 0.6748(3) 0.49171(15) 0.0569(5) Uani 1 1 d . . . . .
H16A H 0.428294 0.572829 0.477405 0.068 Uiso 1 1 calc R . . . .
H16B H 0.481230 0.659335 0.484264 0.068 Uiso 1 1 calc R . . . .
C10 C 0.38772(9) 0.7185(3) 0.03847(15) 0.0518(5) Uani 1 1 d . . . . .
H10 H 0.407466 0.744505 0.010895 0.062 Uiso 1 1 calc R . . . .
C1 C 0.15702(11) 0.3012(3) -0.27853(17) 0.0651(6) Uani 1 1 d . . . . .
H1A H 0.120117 0.239840 -0.317425 0.098 Uiso 1 1 calc GR . . . .
H1B H 0.189871 0.238747 -0.267571 0.098 Uiso 1 1 calc GR . . . .
H1C H 0.152461 0.398437 -0.313261 0.098 Uiso 1 1 calc GR . . . .
C15 C 0.40485(11) 0.7990(3) 0.41703(15) 0.0572(5) Uani 1 1 d . . . . .
H15A H 0.372998 0.815460 0.424585 0.069 Uiso 1 1 calc R . . . .
H15B H 0.425833 0.900747 0.430410 0.069 Uiso 1 1 calc R . . . .
C17 C 0.47777(14) 0.7215(4) 0.59809(18) 0.0834(8) Uani 1 1 d . U . . .
H17A H 0.445951 0.738580 0.605652 0.100 Uiso 1 1 calc R . . . .
H17B H 0.499623 0.822184 0.613198 0.100 Uiso 1 1 calc R . . . .
C18 C 0.52110(18) 0.5936(5) 0.6709(2) 0.1059(11) Uani 1 1 d . U . . .
H18A H 0.498885 0.496722 0.660393 0.159 Uiso 1 1 calc GR . . . .
H18B H 0.540558 0.631153 0.737466 0.159 Uiso 1 1 calc GR . . . .
H18C H 0.551286 0.571726 0.660978 0.159 Uiso 1 1 calc GR . . . .
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'
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
C3 N1 H1 118.1 . .
C3 N1 C2 123.74(16) . .
C2 N1 H1 118.1 . .
C14 N2 C15 118.32(17) . .
C13 N2 C14 124.42(16) . .
C13 N2 C15 117.18(18) . .
C7 C8 C3 119.04(15) . .
C9 C8 C7 117.97(16) . .
C9 C8 C3 122.98(16) . .
C6 C7 C8 120.52(16) . .
C12 C7 C8 119.41(15) . .
C12 C7 C6 120.06(16) . .
O1 C14 N2 119.22(18) . .
O1 C14 C6 123.2(2) . .
N2 C14 C6 117.56(16) . .
N1 C3 C8 120.25(15) . .
N1 C3 C4 121.42(18) . .
C4 C3 C8 118.32(17) . .
C7 C6 C14 120.60(18) . .
C5 C6 C7 118.78(17) . .
C5 C6 C14 120.62(16) . .
C7 C12 C13 120.19(16) . .
C11 C12 C7 120.69(17) . .
C11 C12 C13 119.13(18) . .
C6 C5 H5 118.9 . .
C4 C5 C6 122.15(16) . .
C4 C5 H5 118.9 . .
C8 C9 H9 119.4 . .
C10 C9 C8 121.20(17) . .
C10 C9 H9 119.4 . .
C12 C11 H11 120.1 . .
C12 C11 C10 119.90(18) . .
C10 C11 H11 120.1 . .
N1 C2 H2A 109.6 . .
N1 C2 H2B 109.6 . .
N1 C2 C1 110.28(18) . .
H2A C2 H2B 108.1 . .
C1 C2 H2A 109.6 . .
C1 C2 H2B 109.6 . .
O2 C13 N2 119.85(18) . .
O2 C13 C12 123.00(18) . .
N2 C13 C12 117.14(17) . .
C3 C4 H4 119.4 . .
C5 C4 C3 121.17(18) . .
C5 C4 H4 119.4 . .
H16A C16 H16B 107.7 . .
C15 C16 H16A 108.9 . .
C15 C16 H16B 108.9 . .
C17 C16 H16A 108.9 . .
C17 C16 H16B 108.9 . .
C17 C16 C15 113.22(19) . .
C9 C10 C11 120.81(17) . .
C9 C10 H10 119.6 . .
C11 C10 H10 119.6 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
N2 C15 C16 112.07(17) . .
N2 C15 H15A 109.2 . .
N2 C15 H15B 109.2 . .
C16 C15 H15A 109.2 . .
C16 C15 H15B 109.2 . .
H15A C15 H15B 107.9 . .
C16 C17 H17A 109.2 . .
C16 C17 H17B 109.2 . .
C16 C17 C18 112.0(2) . .
H17A C17 H17B 107.9 . .
C18 C17 H17A 109.2 . .
C18 C17 H17B 109.2 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C14 1.225(2) .
O2 C13 1.221(2) .
N1 H1 0.8600 .
N1 C3 1.355(2) .
N1 C2 1.451(3) .
N2 C14 1.396(3) .
N2 C13 1.393(3) .
N2 C15 1.470(2) .
C8 C7 1.421(2) .
C8 C3 1.442(3) .
C8 C9 1.413(2) .
C7 C6 1.411(2) .
C7 C12 1.411(3) .
C14 C6 1.455(3) .
C3 C4 1.398(3) .
C6 C5 1.381(3) .
C12 C11 1.376(3) .
C12 C13 1.474(3) .
C5 H5 0.9300 .
C5 C4 1.380(3) .
C9 H9 0.9300 .
C9 C10 1.368(3) .
C11 H11 0.9300 .
C11 C10 1.391(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C2 C1 1.491(3) .
C4 H4 0.9300 .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C16 C15 1.515(3) .
C16 C17 1.514(3) .
C10 H10 0.9300 .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C17 C18 1.516(4) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
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 C14 C6 C7 -178.08(17) . . . .
O1 C14 C6 C5 1.4(3) . . . .
N1 C3 C4 C5 179.46(16) . . . .
N2 C14 C6 C7 1.4(3) . . . .
N2 C14 C6 C5 -179.09(16) . . . .
C8 C7 C6 C14 178.59(15) . . . .
C8 C7 C6 C5 -0.9(2) . . . .
C8 C7 C12 C11 1.0(3) . . . .
C8 C7 C12 C13 -178.85(15) . . . .
C8 C3 C4 C5 -1.3(3) . . . .
C8 C9 C10 C11 0.2(3) . . . .
C7 C8 C3 N1 -179.37(15) . . . .
C7 C8 C3 C4 1.4(2) . . . .
C7 C8 C9 C10 0.4(3) . . . .
C7 C6 C5 C4 1.0(3) . . . .
C7 C12 C11 C10 -0.5(3) . . . .
C7 C12 C13 O2 178.55(17) . . . .
C7 C12 C13 N2 -0.9(3) . . . .
C14 N2 C13 O2 -178.70(18) . . . .
C14 N2 C13 C12 0.8(3) . . . .
C14 N2 C15 C16 89.9(2) . . . .
C14 C6 C5 C4 -178.46(17) . . . .
C3 N1 C2 C1 -179.83(18) . . . .
C3 C8 C7 C6 -0.3(2) . . . .
C3 C8 C7 C12 179.95(14) . . . .
C3 C8 C9 C10 179.43(17) . . . .
C6 C7 C12 C11 -178.71(16) . . . .
C6 C7 C12 C13 1.4(2) . . . .
C6 C5 C4 C3 0.1(3) . . . .
C12 C7 C6 C14 -1.7(3) . . . .
C12 C7 C6 C5 178.87(15) . . . .
C12 C11 C10 C9 -0.1(3) . . . .
C9 C8 C7 C6 178.77(15) . . . .
C9 C8 C7 C12 -1.0(2) . . . .
C9 C8 C3 N1 1.6(3) . . . .
C9 C8 C3 C4 -177.65(16) . . . .
C11 C12 C13 O2 -1.4(3) . . . .
C11 C12 C13 N2 179.17(16) . . . .
C2 N1 C3 C8 179.11(15) . . . .
C2 N1 C3 C4 -1.6(3) . . . .
C13 N2 C14 O1 178.51(18) . . . .
C13 N2 C14 C6 -1.0(3) . . . .
C13 N2 C15 C16 -87.0(2) . . . .
C13 C12 C11 C10 179.41(17) . . . .
C15 N2 C14 O1 1.9(3) . . . .
C15 N2 C14 C6 -177.64(15) . . . .
C15 N2 C13 O2 -2.1(3) . . . .
C15 N2 C13 C12 177.43(15) . . . .
C15 C16 C17 C18 178.9(3) . . . .
C17 C16 C15 N2 -179.3(2) . . . .
