#------------------------------------------------------------------------------
#$Date: 2021-01-09 08:06:28 +0200 (Sat, 09 Jan 2021) $
#$Revision: 260885 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243720.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2243720
loop_
_publ_author_name
'Zaytsev, Vladimir P.'
'Chervyakova, Lala V.'
'Sorokina, Elena A.'
'Vasilyev, Kirill A.'
'Çelikesir, Sevim Türktekin'
'Akkurt, Mehmet'
'Bhattarai, Ajaya'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of ethyl
 (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylate
;
_journal_coeditor_code           WM5592
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              86
_journal_page_last               90
_journal_paper_doi               10.1107/S2056989020016801
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C20 H19 N O5'
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_chemical_name_systematic
;Ethyl
(4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylate
;
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                81.205(7)
_cell_angle_beta                 70.657(6)
_cell_angle_gamma                72.642(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8100(18)
_cell_length_b                   9.9182(16)
_cell_length_c                   11.165(2)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.609
_cell_measurement_theta_min      2.547
_cell_volume                     877.0(3)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.583
_diffrn_reflns_theta_min         2.155
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            'light beige'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0747P)²+0.2272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                4669
_reflns_number_total             5332
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5592sup1.cif
_cod_data_source_block           I
_cod_database_code               2243720
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.49262(11) 0.82060(9) 0.82393(8) 0.01800(17) Uani d 1 . .
C C2 0.52219(12) 0.77526(10) 1.01557(9) 0.01914(18) Uani d 1 . .
C C3 0.41740(12) 0.69939(10) 1.01089(9) 0.02056(18) Uani d 1 . .
H H3 0.367401 0.639266 1.077116 0.025 Uiso calc 1 . .
C C4 0.39835(11) 0.72876(9) 0.88651(9) 0.01857(17) Uani d 1 . .
C C5 0.29588(12) 0.68264(10) 0.82451(9) 0.02036(18) Uani d 1 . .
H H5 0.297539 0.581687 0.852768 0.024 Uiso calc 1 . .
C C6 0.37337(12) 0.69298(10) 0.67917(9) 0.01928(17) Uani d 1 . .
H H6 0.289113 0.686876 0.639739 0.023 Uiso calc 1 . .
C C7 0.52879(12) 0.57073(10) 0.63456(9) 0.02000(18) Uani d 1 . .
C C8 0.56409(13) 0.76769(10) 0.49121(9) 0.02031(18) Uani d 1 . .
H H8A 0.508910 0.774189 0.425593 0.024 Uiso calc 1 . .
H H8B 0.650611 0.820227 0.458834 0.024 Uiso calc 1 . .
C C9 0.43715(12) 0.82351(9) 0.61653(9) 0.01886(17) Uani d 1 . .
H H9 0.343898 0.902634 0.599506 0.023 Uiso calc 1 . .
C C10 0.52459(12) 0.87442(9) 0.69242(9) 0.01830(17) Uani d 1 . .
C C11 0.78337(12) 0.53580(10) 0.44672(9) 0.01931(18) Uani d 1 . .
C C12 0.84407(13) 0.58679(11) 0.32111(10) 0.0241(2) Uani d 1 . .
H H12 0.786842 0.676487 0.292163 0.029 Uiso calc 1 . .
C C13 0.98773(14) 0.50692(13) 0.23836(11) 0.0308(2) Uani d 1 . .
H H13 1.028278 0.541994 0.153099 0.037 Uiso calc 1 . .
C C14 1.07198(14) 0.37572(13) 0.28046(12) 0.0321(2) Uani d 1 . .
H H14 1.169324 0.320347 0.223866 0.039 Uiso calc 1 . .
C C15 1.01305(14) 0.32603(11) 0.40575(11) 0.0283(2) Uani d 1 . .
H H15 1.071538 0.236753 0.434436 0.034 Uiso calc 1 . .
C C16 0.87003(13) 0.40465(10) 0.48986(10) 0.02336(19) Uani d 1 . .
H H16 0.831446 0.369962 0.575521 0.028 Uiso calc 1 . .
C C17 0.59178(14) 0.78967(11) 1.11582(10) 0.0247(2) Uani d 1 . .
H H17A 0.711689 0.780661 1.078853 0.037 Uiso calc 1 . .
H H17B 0.573698 0.715273 1.183471 0.037 Uiso calc 1 . .
H H17C 0.535888 0.882592 1.151301 0.037 Uiso calc 1 . .
C C18 0.11631(12) 0.77419(11) 0.87182(10) 0.02347(19) Uani d 1 . .
C C19 -0.08020(14) 0.98413(12) 0.82766(12) 0.0312(2) Uani d 1 . .
H H19A -0.098723 1.029690 0.906094 0.037 Uiso calc 1 . .
H H19B -0.166938 0.933475 0.843495 0.037 Uiso calc 1 . .
C C20 -0.08800(16) 1.09358(14) 0.71871(14) 0.0416(3) Uani d 1 . .
H H20A -0.064035 1.046628 0.640874 0.062 Uiso calc 1 . .
H H20B -0.005259 1.146023 0.706811 0.062 Uiso calc 1 . .
H H20C -0.199768 1.159291 0.737594 0.062 Uiso calc 1 . .
N N1 0.63587(10) 0.61915(8) 0.52807(8) 0.01870(16) Uani d 1 . .
O O1 0.56926(8) 0.85082(7) 0.90205(6) 0.01874(14) Uani d 1 . .
O O2 0.55020(10) 0.45051(8) 0.68426(8) 0.02855(17) Uani d 1 . .
O O3 0.61486(10) 0.95404(8) 0.64330(7) 0.02436(16) Uani d 1 . .
O O4 0.01858(11) 0.75061(11) 0.97188(8) 0.0372(2) Uani d 1 . .
O O5 0.08563(9) 0.88584(8) 0.79139(8) 0.02685(17) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 C1 O1 . . 110.30(8) ?
C4 C1 C10 . . 128.08(8) ?
O1 C1 C10 . . 121.47(8) ?
C3 C2 O1 . . 110.50(8) ?
C3 C2 C17 . . 133.13(9) ?
O1 C2 C17 . . 116.36(8) ?
C2 C3 C4 . . 106.32(8) ?
C2 C3 H3 . . 126.8 ?
C4 C3 H3 . . 126.8 ?
C1 C4 C3 . . 106.46(8) ?
C1 C4 C5 . . 121.28(8) ?
C3 C4 C5 . . 132.22(8) ?
C4 C5 C18 . . 107.45(8) ?
C4 C5 C6 . . 109.46(8) ?
C18 C5 C6 . . 113.92(8) ?
C4 C5 H5 . . 108.6 ?
C18 C5 H5 . . 108.6 ?
C6 C5 H5 . . 108.6 ?
C7 C6 C5 . . 111.40(8) ?
C7 C6 C9 . . 102.38(7) ?
C5 C6 C9 . . 118.72(8) ?
C7 C6 H6 . . 107.9 ?
C5 C6 H6 . . 107.9 ?
C9 C6 H6 . . 107.9 ?
O2 C7 N1 . . 126.77(9) ?
O2 C7 C6 . . 125.30(9) ?
N1 C7 C6 . . 107.91(8) ?
N1 C8 C9 . . 102.56(7) ?
N1 C8 H8A . . 111.3 ?
C9 C8 H8A . . 111.3 ?
N1 C8 H8B . . 111.3 ?
C9 C8 H8B . . 111.3 ?
H8A C8 H8B . . 109.2 ?
C8 C9 C10 . . 109.49(8) ?
C8 C9 C6 . . 102.03(7) ?
C10 C9 C6 . . 114.13(7) ?
C8 C9 H9 . . 110.3 ?
C10 C9 H9 . . 110.3 ?
C6 C9 H9 . . 110.3 ?
O3 C10 C1 . . 123.57(9) ?
O3 C10 C9 . . 121.65(8) ?
C1 C10 C9 . . 114.77(8) ?
C12 C11 C16 . . 119.66(9) ?
C12 C11 N1 . . 118.92(8) ?
C16 C11 N1 . . 121.42(9) ?
C13 C12 C11 . . 120.37(10) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C14 C13 C12 . . 119.97(11) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C15 C14 C13 . . 119.64(10) ?
C15 C14 H14 . . 120.2 ?
C13 C14 H14 . . 120.2 ?
C14 C15 C16 . . 121.15(10) ?
C14 C15 H15 . . 119.4 ?
C16 C15 H15 . . 119.4 ?
C15 C16 C11 . . 119.18(10) ?
C15 C16 H16 . . 120.4 ?
C11 C16 H16 . . 120.4 ?
C2 C17 H17A . . 109.5 ?
C2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O4 C18 O5 . . 124.84(10) ?
O4 C18 C5 . . 123.54(10) ?
O5 C18 C5 . . 111.55(8) ?
O5 C19 C20 . . 106.88(9) ?
O5 C19 H19A . . 110.3 ?
C20 C19 H19A . . 110.3 ?
O5 C19 H19B . . 110.3 ?
C20 C19 H19B . . 110.3 ?
H19A C19 H19B . . 108.6 ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C7 N1 C11 . . 126.27(8) ?
C7 N1 C8 . . 111.65(8) ?
C11 N1 C8 . . 121.13(8) ?
C2 O1 C1 . . 106.42(7) ?
C18 O5 C19 . . 116.94(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C4 . 1.3712(12) ?
C1 O1 . 1.3775(11) ?
C1 C10 . 1.4478(12) ?
C2 C3 . 1.3712(13) ?
C2 O1 . 1.3736(11) ?
C2 C17 . 1.4849(13) ?
C3 C4 . 1.4294(13) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.5035(13) ?
C5 C18 . 1.5305(14) ?
C5 C6 . 1.5385(14) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.5282(14) ?
C6 C9 . 1.5420(13) ?
C6 H6 . 1.0000 ?
C7 O2 . 1.2239(12) ?
C7 N1 . 1.3737(12) ?
C8 N1 . 1.4734(12) ?
C8 C9 . 1.5316(13) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5369(13) ?
C9 H9 . 1.0000 ?
C10 O3 . 1.2289(12) ?
C11 C12 . 1.3987(14) ?
C11 C16 . 1.4023(13) ?
C11 N1 . 1.4156(12) ?
C12 C13 . 1.3906(15) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3904(17) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3893(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3897(15) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 O4 . 1.2031(13) ?
C18 O5 . 1.3356(13) ?
C19 O5 . 1.4587(13) ?
C19 C20 . 1.5066(18) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C14 H14 O1 2_766 0.95 2.53 3.4766(16) 172 yes
C17 H17A O4 1_655 0.98 2.51 3.4913(18) 176 yes
C17 H17B O2 2_667 0.98 2.31 3.2441(15) 159 yes
C17 H17C O1 2_677 0.98 2.57 3.4232(14) 145 yes
C19 H19B O1 1_455 0.99 2.54 3.5181(17) 168 yes
C6 H6 <i>Cg</i>4 2_666 1.00 2.71 3.5892(14) 146 yes
C14 H14 <i>Cg</i>1 2_766 0.95 2.93 3.8320(16) 159 yes

_cod_database_fobs_code 2243720
