Crystal structure of 2-butyl-6-(ethylamino)-1H-benzo[de]isoquinoline-1,3(2H)-dione, C18H20N2O2
Liu, Peilian; Jiang, Fangru; Huang, Guiyuan; Sun, Ying; Huang, Liping; Zeitschrift für Kristallographie - New Crystal Structures 235 (2019) 147–149; doi:10.1515/ncrs-2019-0548

data_8105042
_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 f\"ur 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       '\f and \w 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 \l/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/[\s^2^(Fo^2^)+(0.1300P)^2^+2.1670P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2019-0548_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105042
_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)
;