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#$Date: 2023-05-15 12:07:04 +0300 (Mon, 15 May 2023) $
#$Revision: 283774 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/72/8107209.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_8107209
loop_
_publ_author_name
'Wang, Tiantian'
'Su, Yizi'
'Feng, Yunyun'
'Deng, Xin'
'Tan, Yuxing'
_publ_section_title
;
 Crystal structure of methyl
 3-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)propanoate, C16H13NO4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              765
_journal_page_last               766
_journal_paper_doi               10.1515/ncrs-2022-0241
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 93.080(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.930(3)
_cell_length_b                   6.9807(18)
_cell_length_c                   18.954(5)
_cell_measurement_reflns_used    2092
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      2.89
_cell_volume                     1312.0(6)
_computing_cell_refinement       'Bruker SAINT [1]'
_computing_data_collection       'Bruker APEX2 [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6544
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.100
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_min         2.054
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_transmission_factor_max   0.7462
_exptl_transmission_factor_min   0.6963
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0400
_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)+(0.0630P)²+0.0911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1142
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1813
_reflns_number_total             2336
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0241_suppl_001.cif
_cod_data_source_block           jwj091S_a
_cod_original_cell_volume        1311.9(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8107209
_shelx_shelxl_version_number     2018/3
_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   0.975
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.43995(15) 0.7539(2) 0.53015(7) 0.0351(4) Uani 1 1 d . . . . .
C2 C 0.40334(19) 0.7869(2) 0.46021(8) 0.0463(4) Uani 1 1 d . . . . .
H2 H 0.313307 0.809033 0.446599 0.056 Uiso 1 1 calc R U . . .
C3 C 0.5006(2) 0.7874(2) 0.40924(8) 0.0552(5) Uani 1 1 d . . . . .
H3 H 0.474848 0.811025 0.362136 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6326(2) 0.7535(2) 0.42850(9) 0.0540(5) Uani 1 1 d . . . . .
H4 H 0.696017 0.754312 0.394133 0.065 Uiso 1 1 calc R U . . .
C5 C 0.67531(18) 0.7171(2) 0.49974(8) 0.0438(4) Uani 1 1 d . . . . .
C6 C 0.81092(18) 0.6803(3) 0.52299(11) 0.0571(5) Uani 1 1 d . . . . .
H6 H 0.877159 0.679474 0.490119 0.069 Uiso 1 1 calc R U . . .
C7 C 0.84657(18) 0.6462(3) 0.59194(11) 0.0571(5) Uani 1 1 d . . . . .
H7 H 0.936254 0.621404 0.605556 0.068 Uiso 1 1 calc R U . . .
C8 C 0.74906(15) 0.6480(2) 0.64288(9) 0.0443(4) Uani 1 1 d . . . . .
H8 H 0.774277 0.624502 0.690045 0.053 Uiso 1 1 calc R U . . .
C9 C 0.61609(14) 0.6846(2) 0.62307(7) 0.0336(3) Uani 1 1 d . . . . .
C10 C 0.57628(15) 0.71910(19) 0.55145(7) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.33646(16) 0.7571(2) 0.58334(8) 0.0366(4) Uani 1 1 d . . . . .
C12 C 0.51446(15) 0.6896(2) 0.67723(7) 0.0344(3) Uani 1 1 d . . . . .
C13 C 0.28072(15) 0.7456(2) 0.70838(8) 0.0378(4) Uani 1 1 d . . . . .
H13A H 0.210057 0.834356 0.692838 0.045 Uiso 1 1 calc R U . . .
H13B H 0.323020 0.793948 0.752144 0.045 Uiso 1 1 calc R U . . .
C14 C 0.21953(16) 0.5498(2) 0.72125(8) 0.0454(4) Uani 1 1 d . . . . .
H14A H 0.186431 0.496725 0.676312 0.055 Uiso 1 1 calc R U . . .
H14B H 0.289671 0.465384 0.740686 0.055 Uiso 1 1 calc R U . . .
C15 C 0.10621(15) 0.5536(2) 0.77041(8) 0.0412(4) Uani 1 1 d . . . . .
C16 C 0.03774(18) 0.6404(3) 0.88320(10) 0.0614(5) Uani 1 1 d . . . . .
H16A H -0.033515 0.719961 0.863399 0.092 Uiso 1 1 calc R U . . .
H16B H 0.073734 0.695963 0.926543 0.092 Uiso 1 1 calc R U . . .
H16C H 0.002903 0.515098 0.892445 0.092 Uiso 1 1 calc R U . . .
N1 N 0.38194(12) 0.73347(16) 0.65429(6) 0.0336(3) Uani 1 1 d . . . . .
O1 O 0.21654(11) 0.77945(19) 0.56834(6) 0.0572(4) Uani 1 1 d . . . . .
O2 O 0.54267(11) 0.65881(18) 0.73959(5) 0.0506(3) Uani 1 1 d . . . . .
O3 O -0.00549(12) 0.4978(2) 0.75541(6) 0.0703(4) Uani 1 1 d . . . . .
O4 O 0.14359(10) 0.62542(18) 0.83370(6) 0.0504(3) 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'
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
C15 O4 C16 115.63(13) . .
C12 N1 C11 124.91(12) . .
C12 N1 C13 117.48(12) . .
C11 N1 C13 117.52(12) . .
C8 C9 C10 120.52(13) . .
C8 C9 C12 119.70(13) . .
C10 C9 C12 119.78(13) . .
C2 C1 C10 120.27(14) . .
C2 C1 C11 119.84(15) . .
C10 C1 C11 119.89(13) . .
C1 C10 C9 121.19(13) . .
C1 C10 C5 119.41(14) . .
C9 C10 C5 119.40(14) . .
O1 C11 N1 119.86(14) . .
O1 C11 C1 123.29(14) . .
N1 C11 C1 116.85(13) . .
N1 C13 C14 110.66(12) . .
N1 C13 H13A 109.5 . .
C14 C13 H13A 109.5 . .
N1 C13 H13B 109.5 . .
C14 C13 H13B 109.5 . .
H13A C13 H13B 108.1 . .
O2 C12 N1 120.25(13) . .
O2 C12 C9 122.64(13) . .
N1 C12 C9 117.11(12) . .
O3 C15 O4 123.08(15) . .
O3 C15 C14 124.36(15) . .
O4 C15 C14 112.56(13) . .
C4 C5 C6 124.03(16) . .
C4 C5 C10 118.14(16) . .
C6 C5 C10 117.83(15) . .
C15 C14 C13 113.81(13) . .
C15 C14 H14A 108.8 . .
C13 C14 H14A 108.8 . .
C15 C14 H14B 108.8 . .
C13 C14 H14B 108.8 . .
H14A C14 H14B 107.7 . .
C9 C8 C7 120.06(15) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
C1 C2 C3 120.57(17) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C3 C4 C5 121.40(16) . .
C3 C4 H4 119.3 . .
C5 C4 H4 119.3 . .
C4 C3 C2 120.21(16) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C7 C6 C5 121.71(15) . .
C7 C6 H6 119.1 . .
C5 C6 H6 119.1 . .
C6 C7 C8 120.47(17) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
O4 C16 H16A 109.5 . .
O4 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
O4 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4 C15 1.3343(19) .
O4 C16 1.4498(19) .
O2 C12 1.2189(17) .
O1 C11 1.2194(18) .
N1 C12 1.3975(18) .
N1 C11 1.4051(19) .
N1 C13 1.4762(18) .
O3 C15 1.1954(18) .
C9 C8 1.377(2) .
C9 C10 1.414(2) .
C9 C12 1.478(2) .
C1 C2 1.375(2) .
C1 C10 1.413(2) .
C1 C11 1.478(2) .
C10 C5 1.425(2) .
C13 C14 1.520(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C15 C14 1.499(2) .
C5 C4 1.416(3) .
C5 C6 1.418(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C8 C7 1.404(2) .
C8 H8 0.9300 .
C2 C3 1.402(3) .
C2 H2 0.9300 .
C4 C3 1.363(3) .
C4 H4 0.9300 .
C3 H3 0.9300 .
C6 C7 1.356(3) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 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
C2 C1 C10 C9 -179.93(14) . . . .
C11 C1 C10 C9 0.8(2) . . . .
C2 C1 C10 C5 -0.5(2) . . . .
C11 C1 C10 C5 -179.76(12) . . . .
C8 C9 C10 C1 178.99(14) . . . .
C12 C9 C10 C1 -1.6(2) . . . .
C8 C9 C10 C5 -0.5(2) . . . .
C12 C9 C10 C5 178.99(12) . . . .
C12 N1 C11 O1 173.88(14) . . . .
C13 N1 C11 O1 -2.6(2) . . . .
C12 N1 C11 C1 -6.4(2) . . . .
C13 N1 C11 C1 177.13(12) . . . .
C2 C1 C11 O1 3.4(2) . . . .
C10 C1 C11 O1 -177.32(14) . . . .
C2 C1 C11 N1 -176.34(13) . . . .
C10 C1 C11 N1 2.9(2) . . . .
C12 N1 C13 C14 -87.80(15) . . . .
C11 N1 C13 C14 88.97(15) . . . .
C11 N1 C12 O2 -174.92(14) . . . .
C13 N1 C12 O2 1.6(2) . . . .
C11 N1 C12 C9 5.6(2) . . . .
C13 N1 C12 C9 -177.86(12) . . . .
C8 C9 C12 O2 -1.4(2) . . . .
C10 C9 C12 O2 179.13(14) . . . .
C8 C9 C12 N1 178.00(13) . . . .
C10 C9 C12 N1 -1.45(19) . . . .
C16 O4 C15 O3 -2.7(2) . . . .
C16 O4 C15 C14 177.72(14) . . . .
C1 C10 C5 C4 1.0(2) . . . .
C9 C10 C5 C4 -179.54(14) . . . .
C1 C10 C5 C6 -179.52(14) . . . .
C9 C10 C5 C6 -0.1(2) . . . .
O3 C15 C14 C13 122.04(18) . . . .
O4 C15 C14 C13 -58.42(18) . . . .
N1 C13 C14 C15 -174.39(13) . . . .
C10 C9 C8 C7 0.5(2) . . . .
C12 C9 C8 C7 -178.95(14) . . . .
C10 C1 C2 C3 -0.3(2) . . . .
C11 C1 C2 C3 178.97(14) . . . .
C6 C5 C4 C3 179.79(16) . . . .
C10 C5 C4 C3 -0.8(2) . . . .
C5 C4 C3 C2 0.0(2) . . . .
C1 C2 C3 C4 0.6(2) . . . .
C4 C5 C6 C7 180.00(17) . . . .
C10 C5 C6 C7 0.6(3) . . . .
C5 C6 C7 C8 -0.5(3) . . . .
C9 C8 C7 C6 0.0(3) . . . .
