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#$Date: 2022-06-22 12:07:38 +0300 (Wed, 22 Jun 2022) $
#$Revision: 276148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105449.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_8105449
loop_
_publ_author_name
'Fang, Bo'
'Meng, Jiang Ping'
'Luo, Yan'
_publ_section_title
;
 Crystal structure of methyl
 2-(6,11-dioxo-2,3,6,11-tetrahydro-1H-benzo[f]pyrrolo[2,1-a]isoindole-5-carbonyl)benzoate,
 C24H17NO5
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1297
_journal_page_last               1299
_journal_paper_doi               10.1515/ncrs-2020-0278
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C24 H17 N O5'
_chemical_formula_sum            'C24 H17 N O5'
_chemical_formula_weight         399.38
_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
_cell_angle_alpha                97.11(3)
_cell_angle_beta                 103.23(3)
_cell_angle_gamma                113.33(3)
_cell_formula_units_Z            2
_cell_length_a                   8.5858(2)
_cell_length_b                   9.2397(4)
_cell_length_c                   13.7831(8)
_cell_measurement_reflns_used    1155
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.256
_cell_measurement_theta_min      2.687
_cell_volume                     948.8(4)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4729
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.563
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0545
_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)+(0.0946P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1669
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0278_suppl.cif
_cod_data_source_block           a
_cod_original_cell_volume        948.8(2)
_cod_database_code               8105449
_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   0.983
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
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
O1 O 0.6272(3) 0.6579(2) 0.86948(14) 0.0776(7) Uani 1 1 d . . . . .
O2 O 0.9171(3) 1.28216(19) 1.08863(13) 0.0677(6) Uani 1 1 d . . . . .
O3 O 0.9255(3) 0.8626(2) 0.64640(17) 0.0910(8) Uani 1 1 d . . . . .
O4 O 0.5448(3) 0.8779(3) 0.61771(16) 0.0891(7) Uani 1 1 d . . . . .
O5 O 0.2699(3) 0.6798(4) 0.57571(19) 0.1241(10) Uani 1 1 d . . . . .
N1 N 0.9611(3) 1.1060(2) 0.79999(15) 0.0490(5) Uani 1 1 d . . . . .
C1 C 0.6391(3) 0.8460(3) 1.00742(17) 0.0449(6) Uani 1 1 d . . . . .
C2 C 0.5175(3) 0.7240(3) 1.03674(19) 0.0547(7) Uani 1 1 d . . . . .
H2 H 0.468475 0.617460 0.998578 0.066 Uiso 1 1 calc R . . . .
C3 C 0.4672(4) 0.7572(3) 1.1216(2) 0.0625(7) Uani 1 1 d . . . . .
H3 H 0.385410 0.673327 1.140561 0.075 Uiso 1 1 calc R . . . .
C4 C 0.5385(4) 0.9153(3) 1.1787(2) 0.0613(7) Uani 1 1 d . . . . .
H4 H 0.502999 0.938538 1.235258 0.074 Uiso 1 1 calc R . . . .
C5 C 0.6622(4) 1.0379(3) 1.15125(19) 0.0545(7) Uani 1 1 d . . . . .
H5 H 0.712506 1.143584 1.190906 0.065 Uiso 1 1 calc R . . . .
C6 C 0.7134(3) 1.0069(3) 1.06544(17) 0.0448(6) Uani 1 1 d . . . . .
C7 C 0.8429(3) 1.1426(3) 1.03530(18) 0.0489(6) Uani 1 1 d . . . . .
C8 C 0.8713(3) 1.0982(3) 0.93797(18) 0.0454(6) Uani 1 1 d . . . . .
C9 C 0.7959(3) 0.9371(3) 0.87682(17) 0.0441(6) Uani 1 1 d . . . . .
C10 C 0.6839(3) 0.8013(3) 0.91217(18) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.8536(3) 0.9435(3) 0.79034(18) 0.0458(6) Uani 1 1 d . . . . .
C12 C 0.9724(3) 1.1990(3) 0.88761(19) 0.0498(6) Uani 1 1 d . . . . .
C13 C 1.0858(4) 1.3733(3) 0.8977(2) 0.0692(8) Uani 1 1 d . . . . .
H13A H 1.192215 1.415036 0.956237 0.083 Uiso 1 1 calc R . . . .
H13B H 1.021135 1.437300 0.905470 0.083 Uiso 1 1 calc R . . . .
C14 C 1.1326(4) 1.3758(3) 0.7973(2) 0.0776(9) Uani 1 1 d . . . . .
H14A H 1.260456 1.434166 0.811340 0.093 Uiso 1 1 calc R . . . .
H14B H 1.075983 1.429673 0.756142 0.093 Uiso 1 1 calc R . . . .
C15 C 1.0659(4) 1.1990(3) 0.7394(2) 0.0664(8) Uani 1 1 d . . . . .
H15A H 0.992588 1.177981 0.669574 0.080 Uiso 1 1 calc R . . . .
H15B H 1.164620 1.173201 0.738012 0.080 Uiso 1 1 calc R . . . .
C16 C 0.8274(4) 0.8245(3) 0.6993(2) 0.0572(7) Uani 1 1 d . . . . .
C17 C 0.6854(4) 0.6530(3) 0.67201(19) 0.0547(7) Uani 1 1 d . . . . .
C18 C 0.7432(5) 0.5330(4) 0.6841(2) 0.0717(8) Uani 1 1 d . . . . .
H18 H 0.863773 0.562387 0.712611 0.086 Uiso 1 1 calc R . . . .
C19 C 0.6240(7) 0.3728(4) 0.6542(3) 0.0949(12) Uani 1 1 d . . . . .
H19 H 0.663755 0.293621 0.662074 0.114 Uiso 1 1 calc R . . . .
C20 C 0.4458(7) 0.3284(5) 0.6126(3) 0.1085(16) Uani 1 1 d . . . . .
H20 H 0.364497 0.219369 0.593698 0.130 Uiso 1 1 calc R . . . .
C21 C 0.3874(5) 0.4465(5) 0.5989(2) 0.0961(13) Uani 1 1 d . . . . .
H21 H 0.266723 0.415697 0.569507 0.115 Uiso 1 1 calc R . . . .
C22 C 0.5058(4) 0.6098(4) 0.62825(19) 0.0628(8) Uani 1 1 d . . . . .
C23 C 0.4476(4) 0.7394(5) 0.6088(2) 0.0738(9) Uani 1 1 d . . . . .
C24 C 0.1989(6) 0.7923(7) 0.5445(4) 0.166(2) Uani 1 1 d . . . . .
H24A H 0.242607 0.832933 0.490478 0.250 Uiso 1 1 calc GR . . . .
H24B H 0.236265 0.881184 0.602127 0.250 Uiso 1 1 calc GR . . . .
H24C H 0.071198 0.736764 0.520386 0.250 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
C23 O5 C24 116.3(4) . .
C11 N1 C15 135.5(2) . .
C12 N1 C11 111.0(2) . .
C12 N1 C15 113.5(2) . .
C2 C1 C6 119.3(2) . .
C2 C1 C10 118.1(2) . .
C6 C1 C10 122.5(2) . .
C1 C2 H2 119.5 . .
C3 C2 C1 121.1(2) . .
C3 C2 H2 119.5 . .
C2 C3 H3 120.0 . .
C2 C3 C4 120.0(3) . .
C4 C3 H3 120.0 . .
C3 C4 H4 120.3 . .
C5 C4 C3 119.5(2) . .
C5 C4 H4 120.3 . .
C4 C5 H5 119.4 . .
C4 C5 C6 121.3(2) . .
C6 C5 H5 119.4 . .
C1 C6 C7 121.0(2) . .
C5 C6 C1 118.8(2) . .
C5 C6 C7 120.2(2) . .
O2 C7 C6 121.7(2) . .
O2 C7 C8 123.0(2) . .
C8 C7 C6 115.3(2) . .
C9 C8 C7 124.7(2) . .
C12 C8 C7 128.1(2) . .
C12 C8 C9 107.2(2) . .
C8 C9 C10 119.9(2) . .
C11 C9 C8 107.9(2) . .
C11 C9 C10 132.2(2) . .
O1 C10 C1 119.7(2) . .
O1 C10 C9 124.2(2) . .
C9 C10 C1 116.0(2) . .
N1 C11 C9 105.92(19) . .
N1 C11 C16 118.3(2) . .
C9 C11 C16 135.8(2) . .
N1 C12 C8 108.0(2) . .
N1 C12 C13 111.2(2) . .
C8 C12 C13 140.8(2) . .
C12 C13 H13A 111.0 . .
C12 C13 H13B 111.0 . .
C12 C13 C14 103.8(2) . .
H13A C13 H13B 109.0 . .
C14 C13 H13A 111.0 . .
C14 C13 H13B 111.0 . .
C13 C14 H14A 110.2 . .
C13 C14 H14B 110.2 . .
C13 C14 C15 107.7(2) . .
H14A C14 H14B 108.5 . .
C15 C14 H14A 110.2 . .
C15 C14 H14B 110.2 . .
N1 C15 C14 103.0(2) . .
N1 C15 H15A 111.2 . .
N1 C15 H15B 111.2 . .
C14 C15 H15A 111.2 . .
C14 C15 H15B 111.2 . .
H15A C15 H15B 109.1 . .
O3 C16 C11 120.1(2) . .
O3 C16 C17 118.5(2) . .
C11 C16 C17 121.4(2) . .
C18 C17 C16 116.5(3) . .
C22 C17 C16 123.2(3) . .
C22 C17 C18 120.0(3) . .
C17 C18 H18 119.8 . .
C19 C18 C17 120.5(3) . .
C19 C18 H18 119.8 . .
C18 C19 H19 119.9 . .
C18 C19 C20 120.2(4) . .
C20 C19 H19 119.9 . .
C19 C20 H20 120.1 . .
C19 C20 C21 119.8(4) . .
C21 C20 H20 120.1 . .
C20 C21 H21 119.4 . .
C22 C21 C20 121.1(4) . .
C22 C21 H21 119.4 . .
C17 C22 C23 119.3(3) . .
C21 C22 C17 118.4(3) . .
C21 C22 C23 122.1(3) . .
O4 C23 O5 123.0(4) . .
O4 C23 C22 125.2(3) . .
O5 C23 C22 111.7(4) . .
O5 C24 H24A 109.5 . .
O5 C24 H24B 109.5 . .
O5 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.226(3) .
O2 C7 1.229(3) .
O3 C16 1.215(3) .
O4 C23 1.191(4) .
O5 C23 1.339(4) .
O5 C24 1.459(5) .
N1 C11 1.385(3) .
N1 C12 1.353(3) .
N1 C15 1.467(3) .
C1 C2 1.378(3) .
C1 C6 1.406(3) .
C1 C10 1.505(3) .
C2 H2 0.9300 .
C2 C3 1.377(4) .
C3 H3 0.9300 .
C3 C4 1.384(4) .
C4 H4 0.9300 .
C4 C5 1.375(4) .
C5 H5 0.9300 .
C5 C6 1.388(3) .
C6 C7 1.489(3) .
C7 C8 1.456(3) .
C8 C9 1.422(3) .
C8 C12 1.377(3) .
C9 C10 1.465(3) .
C9 C11 1.391(3) .
C11 C16 1.472(3) .
C12 C13 1.484(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.528(4) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 C15 1.536(4) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.501(4) .
C17 C18 1.395(4) .
C17 C22 1.388(4) .
C18 H18 0.9300 .
C18 C19 1.365(5) .
C19 H19 0.9300 .
C19 C20 1.371(6) .
C20 H20 0.9300 .
C20 C21 1.386(6) .
C21 H21 0.9300 .
C21 C22 1.385(5) .
C22 C23 1.499(5) .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
