#------------------------------------------------------------------------------
#$Date: 2020-06-06 01:30:59 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252950 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/21/2022152.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_2022152
loop_
_publ_author_name
'Becerra, Diana'
'Castillo, Juan'
'Insuasty, Braulio'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Synthesis of N-substituted
 3-(2-aryl-2-oxoethyl)-3-hydroxyindolin-2-ones and their conversion to
 N-substituted (E)-3-(2-aryl-2-oxoethylidene)indolin-2-ones:
 synthetic sequence, spectroscopic characterization and structures of four
 3-hydroxy compounds and five oxoethylidene products
;
_journal_coeditor_code           SK3748
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              433
_journal_page_last               445
_journal_paper_doi               10.1107/S2053229620004143
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C24 H19 N O5'
_chemical_formula_moiety         'C24 H19 N O5'
_chemical_formula_sum            'C24 H19 N O5'
_chemical_formula_weight         401.40
_chemical_name_systematic
3-[2-(Benzo[d][1,3]dioxol-5-yl)-2-oxoethyl]-1-benzyl-3-hydroxyindolin-2-one
_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   mixed
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                93.084(3)
_cell_angle_beta                 101.883(2)
_cell_angle_gamma                95.055(2)
_cell_formula_units_Z            4
_cell_length_a                   11.8136(7)
_cell_length_b                   12.4987(10)
_cell_length_c                   13.5976(11)
_cell_measurement_reflns_used    9692
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.296
_cell_measurement_theta_min      2.162
_cell_volume                     1951.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            125792
_diffrn_reflns_theta_full        28.296
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_min         2.162
_diffrn_source
'INCOATEC high brilliance microfocus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     547
_refine_ls_number_reflns         9691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0393
_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)+(0.0386P)²+1.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                8134
_reflns_number_total             9691
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3748sup1.cif
_cod_data_source_block           If
_cod_database_code               2022152
_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   0.976
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2.014
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
N N11 0.36578(9) 0.70223(8) 0.75521(8) 0.0180(2) Uani d 1 . .
C C12 0.33088(10) 0.64863(9) 0.66308(9) 0.0163(2) Uani d 1 . .
O O12 0.39483(7) 0.62008(7) 0.60785(7) 0.02009(18) Uani d 1 . .
C C13 0.19674(10) 0.63051(9) 0.63676(9) 0.0155(2) Uani d 1 . .
O O13 0.15366(8) 0.68949(7) 0.55269(7) 0.01875(17) Uani d 1 . .
H H13 0.1495(15) 0.6486(14) 0.4976(13) 0.028 Uiso d 1 . .
C C13A 0.16621(10) 0.68140(9) 0.72932(9) 0.0162(2) Uani d 1 . .
C C14 0.05913(11) 0.69289(10) 0.75156(9) 0.0198(2) Uani d 1 . .
H H14 -0.0104 0.6659 0.7051 0.024 Uiso calc 1 . .
C C15 0.05531(11) 0.74530(10) 0.84426(10) 0.0223(2) Uani d 1 . .
H H15 -0.0176 0.7544 0.8610 0.027 Uiso calc 1 . .
C C16 0.15748(12) 0.78406(10) 0.91178(10) 0.0222(2) Uani d 1 . .
H H16 0.1533 0.8188 0.9746 0.027 Uiso calc 1 . .
C C17 0.26690(11) 0.77310(10) 0.88929(9) 0.0203(2) Uani d 1 . .
H H17 0.3368 0.7999 0.9354 0.024 Uiso calc 1 . .
C C17A 0.26833(10) 0.72162(9) 0.79709(9) 0.0170(2) Uani d 1 . .
C C11 0.48659(10) 0.72091(10) 0.80967(10) 0.0207(2) Uani d 1 . .
H H11A 0.5360 0.6858 0.7697 0.025 Uiso calc 1 . .
H H11B 0.4943 0.6865 0.8743 0.025 Uiso calc 1 . .
C C111 0.53080(10) 0.83877(10) 0.83120(10) 0.0197(2) Uani d 1 . .
C C112 0.52255(12) 0.90761(11) 0.75373(10) 0.0259(3) Uani d 1 . .
H H112 0.4860 0.8815 0.6868 0.031 Uiso calc 1 . .
C C113 0.56794(13) 1.01485(12) 0.77435(12) 0.0317(3) Uani d 1 . .
H H113 0.5618 1.0620 0.7214 0.038 Uiso calc 1 . .
C C114 0.62220(13) 1.05348(12) 0.87201(12) 0.0328(3) Uani d 1 . .
H H114 0.6536 1.1267 0.8857 0.039 Uiso calc 1 . .
C C115 0.63031(13) 0.98508(12) 0.94904(11) 0.0306(3) Uani d 1 . .
H H115 0.6675 1.0111 1.0158 0.037 Uiso calc 1 . .
C C116 0.58414(11) 0.87823(11) 0.92887(10) 0.0244(3) Uani d 1 . .
H H116 0.5890 0.8317 0.9822 0.029 Uiso calc 1 . .
C C131 0.15502(10) 0.51079(9) 0.61318(9) 0.0160(2) Uani d 1 . .
H H13A 0.0695 0.5013 0.6056 0.019 Uiso calc 1 . .
H H13B 0.1726 0.4874 0.5477 0.019 Uiso calc 1 . .
C C132 0.20854(10) 0.43795(9) 0.69182(9) 0.0160(2) Uani d 1 . .
O O132 0.27327(8) 0.47573(7) 0.77033(7) 0.02184(19) Uani d 1 . .
O O141 0.12237(10) -0.00809(8) 0.62667(9) 0.0338(2) Uani d 1 . .
C C142 0.20004(14) -0.03580(11) 0.71514(12) 0.0309(3) Uani d 1 . .
H H14A 0.1567 -0.0811 0.7554 0.037 Uiso calc 1 . .
H H14B 0.2609 -0.0770 0.6958 0.037 Uiso calc 1 . .
O O143 0.25219(10) 0.06174(8) 0.77321(8) 0.0332(2) Uani d 1 . .
C C14A 0.20977(11) 0.14395(10) 0.71810(10) 0.0218(2) Uani d 1 . .
C C144 0.23604(11) 0.25218(10) 0.74070(9) 0.0195(2) Uani d 1 . .
H H144 0.2886 0.2805 0.8010 0.023 Uiso calc 1 . .
C C145 0.18104(10) 0.32004(9) 0.66977(9) 0.0167(2) Uani d 1 . .
C C146 0.10375(10) 0.27679(10) 0.58197(9) 0.0195(2) Uani d 1 . .
H H146 0.0680 0.3242 0.5355 0.023 Uiso calc 1 . .
C C147 0.07750(11) 0.16566(10) 0.56043(10) 0.0232(3) Uani d 1 . .
H H147 0.0248 0.1360 0.5008 0.028 Uiso calc 1 . .
C C18A 0.13246(11) 0.10199(10) 0.63066(10) 0.0230(3) Uani d 1 . .
N N21 0.14702(8) 0.57608(8) 0.21220(8) 0.0171(2) Uani d 1 . .
C C22 0.18051(10) 0.56438(9) 0.31195(9) 0.0164(2) Uani d 1 . .
O O22 0.11699(7) 0.56189(7) 0.37299(6) 0.01978(18) Uani d 1 . .
C C23 0.31364(10) 0.55891(9) 0.33838(9) 0.0153(2) Uani d 1 . .
O O23 0.36630(7) 0.65315(7) 0.40061(7) 0.01939(18) Uani d 1 . .
H H23 0.3659(15) 0.6426(14) 0.4653(14) 0.029 Uiso d 1 . .
C C23A 0.34379(10) 0.56497(9) 0.23629(9) 0.0171(2) Uani d 1 . .
C C24 0.44927(11) 0.56227(10) 0.20825(10) 0.0207(2) Uani d 1 . .
H H24 0.5185 0.5574 0.2570 0.025 Uiso calc 1 . .
C C25 0.45181(12) 0.56686(11) 0.10592(10) 0.0238(3) Uani d 1 . .
H H25 0.5235 0.5650 0.0849 0.029 Uiso calc 1 . .
C C26 0.35020(12) 0.57406(11) 0.03520(10) 0.0245(3) Uani d 1 . .
H H26 0.3532 0.5753 -0.0340 0.029 Uiso calc 1 . .
C C27 0.24316(11) 0.57957(10) 0.06365(10) 0.0215(2) Uani d 1 . .
H H27 0.1740 0.5866 0.0155 0.026 Uiso calc 1 . .
C C27A 0.24281(10) 0.57436(9) 0.16460(9) 0.0175(2) Uani d 1 . .
C C21 0.02682(10) 0.57967(10) 0.16062(9) 0.0199(2) Uani d 1 . .
H H21A -0.0246 0.5556 0.2059 0.024 Uiso calc 1 . .
H H21B 0.0097 0.5281 0.1003 0.024 Uiso calc 1 . .
C C211 -0.00175(11) 0.68995(10) 0.12808(9) 0.0207(2) Uani d 1 . .
C C212 0.05811(13) 0.78375(11) 0.17857(11) 0.0283(3) Uani d 1 . .
H H212 0.1215 0.7799 0.2336 0.034 Uiso calc 1 . .
C C213 0.02605(15) 0.88369(13) 0.14936(13) 0.0378(4) Uani d 1 . .
H H213 0.0680 0.9478 0.1841 0.045 Uiso calc 1 . .
C C214 -0.06704(15) 0.88994(13) 0.06965(13) 0.0372(4) Uani d 1 . .
H H214 -0.0893 0.9582 0.0500 0.045 Uiso calc 1 . .
C C215 -0.12708(13) 0.79678(14) 0.01898(12) 0.0337(3) Uani d 1 . .
H H215 -0.1907 0.8009 -0.0358 0.040 Uiso calc 1 . .
C C216 -0.09496(12) 0.69690(12) 0.04770(10) 0.0271(3) Uani d 1 . .
H H216 -0.1367 0.6330 0.0124 0.032 Uiso calc 1 . .
C C231 0.34489(10) 0.45854(9) 0.39264(9) 0.0168(2) Uani d 1 . .
H H23A 0.4296 0.4544 0.4009 0.020 Uiso calc 1 . .
H H23B 0.3279 0.4665 0.4608 0.020 Uiso calc 1 . .
C C232 0.28175(10) 0.35343(9) 0.34022(9) 0.0170(2) Uani d 1 . .
O O232 0.21756(8) 0.35194(7) 0.25714(7) 0.02298(19) Uani d 1 . .
O O241 0.34212(10) -0.03455(9) 0.51919(9) 0.0387(3) Uani d 1 . .
C C242 0.25730(16) -0.10257(12) 0.44568(13) 0.0373(4) Uani d 1 . .
H H24A 0.2936 -0.1640 0.4205 0.045 Uiso calc 1 . .
H H24B 0.1930 -0.1314 0.4764 0.045 Uiso calc 1 . .
O O243 0.21368(12) -0.03916(9) 0.36449(9) 0.0452(3) Uani d 1 . .
C C24A 0.25954(13) 0.06508(11) 0.39521(11) 0.0274(3) Uani d 1 . .
C C244 0.23952(12) 0.15577(10) 0.34531(10) 0.0246(3) Uani d 1 . .
H H244 0.1874 0.1532 0.2817 0.030 Uiso calc 1 . .
C C245 0.29995(10) 0.25330(10) 0.39278(9) 0.0189(2) Uani d 1 . .
C C246 0.37567(11) 0.25505(11) 0.48632(10) 0.0235(3) Uani d 1 . .
H H246 0.4147 0.3219 0.5173 0.028 Uiso calc 1 . .
C C247 0.39570(12) 0.16122(12) 0.53564(11) 0.0288(3) Uani d 1 . .
H H247 0.4477 0.1624 0.5991 0.035 Uiso calc 1 . .
C C28A 0.33634(12) 0.06743(11) 0.48759(11) 0.0276(3) 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
C12 N11 C17A . . 110.46(10) ?
C12 N11 C11 . . 124.04(10) ?
C17A N11 C11 . . 124.77(10) ?
O12 C12 N11 . . 126.00(11) ?
O12 C12 C13 . . 124.91(11) ?
N11 C12 C13 . . 109.08(10) ?
O13 C13 C13A . . 109.04(9) ?
O13 C13 C131 . . 110.14(9) ?
C13A C13 C131 . . 115.27(10) ?
O13 C13 C12 . . 109.43(9) ?
C13A C13 C12 . . 101.69(9) ?
C131 C13 C12 . . 110.90(9) ?
C13 O13 H13 . . 108.4(11) ?
C14 C13A C17A . . 120.87(11) ?
C14 C13A C13 . . 130.11(11) ?
C17A C13A C13 . . 109.02(10) ?
C13A C14 C15 . . 118.39(12) ?
C13A C14 H14 . . 120.8 ?
C15 C14 H14 . . 120.8 ?
C16 C15 C14 . . 120.37(12) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C17 . . 121.50(12) ?
C15 C16 H16 . . 119.2 ?
C17 C16 H16 . . 119.2 ?
C17A C17 C16 . . 117.02(12) ?
C17A C17 H17 . . 121.5 ?
C16 C17 H17 . . 121.5 ?
C17 C17A C13A . . 121.86(11) ?
C17 C17A N11 . . 128.41(11) ?
C13A C17A N11 . . 109.73(10) ?
N11 C11 C111 . . 113.60(10) ?
N11 C11 H11A . . 108.8 ?
C111 C11 H11A . . 108.8 ?
N11 C11 H11B . . 108.8 ?
C111 C11 H11B . . 108.8 ?
H11A C11 H11B . . 107.7 ?
C112 C111 C116 . . 119.45(12) ?
C112 C111 C11 . . 120.65(11) ?
C116 C111 C11 . . 119.86(12) ?
C111 C112 C113 . . 119.85(13) ?
C111 C112 H112 . . 120.1 ?
C113 C112 H112 . . 120.1 ?
C114 C113 C112 . . 120.38(14) ?
C114 C113 H113 . . 119.8 ?
C112 C113 H113 . . 119.8 ?
C115 C114 C113 . . 119.77(13) ?
C115 C114 H114 . . 120.1 ?
C113 C114 H114 . . 120.1 ?
C114 C115 C116 . . 120.00(13) ?
C114 C115 H115 . . 120.0 ?
C116 C115 H115 . . 120.0 ?
C115 C116 C111 . . 120.55(13) ?
C115 C116 H116 . . 119.7 ?
C111 C116 H116 . . 119.7 ?
C132 C131 C13 . . 114.79(9) ?
C132 C131 H13A . . 108.6 ?
C13 C131 H13A . . 108.6 ?
C132 C131 H13B . . 108.6 ?
C13 C131 H13B . . 108.6 ?
H13A C131 H13B . . 107.5 ?
O132 C132 C145 . . 121.30(11) ?
O132 C132 C131 . . 120.76(10) ?
C145 C132 C131 . . 117.93(10) ?
C18A O141 C142 . . 105.91(11) ?
O143 C142 O141 . . 108.36(10) ?
O143 C142 H14A . . 110.0 ?
O141 C142 H14A . . 110.0 ?
O143 C142 H14B . . 110.0 ?
O141 C142 H14B . . 110.0 ?
H14A C142 H14B . . 108.4 ?
C14A O143 C142 . . 105.69(11) ?
C144 C14A O143 . . 127.95(12) ?
C144 C14A C18A . . 122.10(12) ?
O143 C14A C18A . . 109.95(11) ?
C14A C144 C145 . . 116.55(11) ?
C14A C144 H144 . . 121.7 ?
C145 C144 H144 . . 121.7 ?
C146 C145 C144 . . 120.77(11) ?
C146 C145 C132 . . 121.42(11) ?
C144 C145 C132 . . 117.81(11) ?
C145 C146 C147 . . 121.82(11) ?
C145 C146 H146 . . 119.1 ?
C147 C146 H146 . . 119.1 ?
C18A C147 C146 . . 116.00(12) ?
C18A C147 H147 . . 122.0 ?
C146 C147 H147 . . 122.0 ?
O141 C18A C147 . . 127.20(12) ?
O141 C18A C14A . . 110.03(11) ?
C147 C18A C14A . . 122.77(12) ?
C22 N21 C27A . . 110.76(10) ?
C22 N21 C21 . . 123.82(10) ?
C27A N21 C21 . . 125.18(10) ?
O22 C22 N21 . . 125.99(11) ?
O22 C22 C23 . . 124.97(11) ?
N21 C22 C23 . . 109.00(10) ?
O23 C23 C23A . . 109.13(9) ?
O23 C23 C231 . . 109.93(9) ?
C23A C23 C231 . . 115.70(9) ?
O23 C23 C22 . . 108.55(9) ?
C23A C23 C22 . . 101.49(9) ?
C231 C23 C22 . . 111.59(9) ?
C23 O23 H23 . . 109.7(11) ?
C24 C23A C27A . . 120.57(11) ?
C24 C23A C23 . . 130.41(11) ?
C27A C23A C23 . . 109.02(10) ?
C23A C24 C25 . . 118.35(12) ?
C23A C24 H24 . . 120.8 ?
C25 C24 H24 . . 120.8 ?
C26 C25 C24 . . 120.40(12) ?
C26 C25 H25 . . 119.8 ?
C24 C25 H25 . . 119.8 ?
C25 C26 C27 . . 121.46(12) ?
C25 C26 H26 . . 119.3 ?
C27 C26 H26 . . 119.3 ?
C27A C27 C26 . . 117.03(12) ?
C27A C27 H27 . . 121.5 ?
C26 C27 H27 . . 121.5 ?
C27 C27A C23A . . 122.16(11) ?
C27 C27A N21 . . 128.18(11) ?
C23A C27A N21 . . 109.66(10) ?
N21 C21 C211 . . 114.11(10) ?
N21 C21 H21A . . 108.7 ?
C211 C21 H21A . . 108.7 ?
N21 C21 H21B . . 108.7 ?
C211 C21 H21B . . 108.7 ?
H21A C21 H21B . . 107.6 ?
C212 C211 C216 . . 119.10(12) ?
C212 C211 C21 . . 122.04(12) ?
C216 C211 C21 . . 118.79(12) ?
C211 C212 C213 . . 120.46(14) ?
C211 C212 H212 . . 119.8 ?
C213 C212 H212 . . 119.8 ?
C214 C213 C212 . . 120.11(15) ?
C214 C213 H213 . . 119.9 ?
C212 C213 H213 . . 119.9 ?
C215 C214 C213 . . 119.74(14) ?
C215 C214 H214 . . 120.1 ?
C213 C214 H214 . . 120.1 ?
C214 C215 C216 . . 120.27(14) ?
C214 C215 H215 . . 119.9 ?
C216 C215 H215 . . 119.9 ?
C215 C216 C211 . . 120.32(14) ?
C215 C216 H216 . . 119.8 ?
C211 C216 H216 . . 119.8 ?
C232 C231 C23 . . 115.06(10) ?
C232 C231 H23A . . 108.5 ?
C23 C231 H23A . . 108.5 ?
C232 C231 H23B . . 108.5 ?
C23 C231 H23B . . 108.5 ?
H23A C231 H23B . . 107.5 ?
O232 C232 C245 . . 121.35(11) ?
O232 C232 C231 . . 120.52(11) ?
C245 C232 C231 . . 118.12(10) ?
C28A O241 C242 . . 105.66(12) ?
O243 C242 O241 . . 107.99(11) ?
O243 C242 H24A . . 110.1 ?
O241 C242 H24A . . 110.1 ?
O243 C242 H24B . . 110.1 ?
O241 C242 H24B . . 110.1 ?
H24A C242 H24B . . 108.4 ?
C24A O243 C242 . . 105.97(12) ?
C244 C24A O243 . . 128.03(14) ?
C244 C24A C28A . . 122.26(13) ?
O243 C24A C28A . . 109.68(12) ?
C24A C244 C245 . . 116.73(12) ?
C24A C244 H244 . . 121.6 ?
C245 C244 H244 . . 121.6 ?
C246 C245 C244 . . 120.57(12) ?
C246 C245 C232 . . 121.11(11) ?
C244 C245 C232 . . 118.32(11) ?
C245 C246 C247 . . 121.78(13) ?
C245 C246 H246 . . 119.1 ?
C247 C246 H246 . . 119.1 ?
C28A C247 C246 . . 116.47(13) ?
C28A C247 H247 . . 121.8 ?
C246 C247 H247 . . 121.8 ?
O241 C28A C247 . . 127.70(14) ?
O241 C28A C24A . . 110.12(13) ?
C247 C28A C24A . . 122.18(12) ?
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
N11 C12 . 1.3551(15) ?
N11 C17A . 1.4186(15) ?
N11 C11 . 1.4585(15) ?
C12 O12 . 1.2306(14) ?
C12 C13 . 1.5444(16) ?
C13 O13 . 1.4235(14) ?
C13 C13A . 1.5033(16) ?
C13 C131 . 1.5291(16) ?
O13 H13 . 0.874(18) ?
C13A C14 . 1.3774(16) ?
C13A C17A . 1.3939(16) ?
C14 C15 . 1.3999(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3883(19) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.4045(17) ?
C16 H16 . 0.9500 ?
C17 C17A . 1.3820(17) ?
C17 H17 . 0.9500 ?
C11 C111 . 1.5111(17) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C111 C112 . 1.3892(19) ?
C111 C116 . 1.3907(18) ?
C112 C113 . 1.391(2) ?
C112 H112 . 0.9500 ?
C113 C114 . 1.391(2) ?
C113 H113 . 0.9500 ?
C114 C115 . 1.381(2) ?
C114 H114 . 0.9500 ?
C115 C116 . 1.3882(19) ?
C115 H115 . 0.9500 ?
C116 H116 . 0.9500 ?
C131 C132 . 1.5166(16) ?
C131 H13A . 0.9900 ?
C131 H13B . 0.9900 ?
C132 O132 . 1.2221(15) ?
C132 C145 . 1.4816(16) ?
O141 C18A . 1.3676(15) ?
O141 C142 . 1.4336(18) ?
C142 O143 . 1.4328(17) ?
C142 H14A . 0.9900 ?
C142 H14B . 0.9900 ?
O143 C14A . 1.3738(15) ?
C14A C144 . 1.3649(17) ?
C14A C18A . 1.3872(19) ?
C144 C145 . 1.4138(16) ?
C144 H144 . 0.9500 ?
C145 C146 . 1.3950(17) ?
C146 C147 . 1.3979(17) ?
C146 H146 . 0.9500 ?
C147 C18A . 1.3727(18) ?
C147 H147 . 0.9500 ?
N21 C22 . 1.3522(15) ?
N21 C27A . 1.4158(15) ?
N21 C21 . 1.4542(15) ?
C22 O22 . 1.2280(14) ?
C22 C23 . 1.5480(16) ?
C23 O23 . 1.4273(14) ?
C23 C23A . 1.5066(16) ?
C23 C231 . 1.5243(16) ?
O23 H23 . 0.898(18) ?
C23A C24 . 1.3788(16) ?
C23A C27A . 1.3947(16) ?
C24 C25 . 1.4020(18) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.3881(19) ?
C25 H25 . 0.9500 ?
C26 C27 . 1.4027(18) ?
C26 H26 . 0.9500 ?
C27 C27A . 1.3785(17) ?
C27 H27 . 0.9500 ?
C21 C211 . 1.5152(17) ?
C21 H21A . 0.9900 ?
C21 H21B . 0.9900 ?
C211 C212 . 1.3831(19) ?
C211 C216 . 1.3951(18) ?
C212 C213 . 1.392(2) ?
C212 H212 . 0.9500 ?
C213 C214 . 1.387(2) ?
C213 H213 . 0.9500 ?
C214 C215 . 1.379(2) ?
C214 H214 . 0.9500 ?
C215 C216 . 1.389(2) ?
C215 H215 . 0.9500 ?
C216 H216 . 0.9500 ?
C231 C232 . 1.5158(16) ?
C231 H23A . 0.9900 ?
C231 H23B . 0.9900 ?
C232 O232 . 1.2223(15) ?
C232 C245 . 1.4846(16) ?
O241 C28A . 1.3697(16) ?
O241 C242 . 1.440(2) ?
C242 O243 . 1.4297(19) ?
C242 H24A . 0.9900 ?
C242 H24B . 0.9900 ?
O243 C24A . 1.3745(17) ?
C24A C244 . 1.3657(19) ?
C24A C28A . 1.387(2) ?
C244 C245 . 1.4087(18) ?
C244 H244 . 0.9500 ?
C245 C246 . 1.3940(18) ?
C246 C247 . 1.3961(18) ?
C246 H246 . 0.9500 ?
C247 C28A . 1.370(2) ?
C247 H247 . 0.9500 ?
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
O13 H13 O22 . 0.874(17) 1.912(17) 2.7794(12) 171.1(17) no
O23 H23 O12 . 0.897(18) 1.938(19) 2.8256(13) 169.8(17) no
C131 H13A O22 2_566 0.99 2.35 3.3075(16) 161 no
C147 H147 O141 2_556 0.95 2.56 3.4776(18) 163 no
C231 H23A O12 2_666 0.99 2.37 3.3107(15) 159 no
C242 H24A O23 1_545 0.99 2.53 3.4889(19) 163 no
C142 H14A Cg3 1_545 0.99 2.53 3.3289(15) 137 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17A N11 C12 O12 . . . . -179.90(11) ?
C11 N11 C12 O12 . . . . -9.28(19) ?
C17A N11 C12 C13 . . . . 1.18(13) ?
C11 N11 C12 C13 . . . . 171.80(10) ?
O12 C12 C13 O13 . . . . -64.35(15) ?
N11 C12 C13 O13 . . . . 114.58(11) ?
O12 C12 C13 C13A . . . . -179.59(11) ?
N11 C12 C13 C13A . . . . -0.65(12) ?
O12 C12 C13 C131 . . . . 57.35(15) ?
N11 C12 C13 C131 . . . . -123.72(10) ?
O13 C13 C13A C14 . . . . 63.36(16) ?
C131 C13 C13A C14 . . . . -61.09(16) ?
C12 C13 C13A C14 . . . . 178.88(12) ?
O13 C13 C13A C17A . . . . -115.62(10) ?
C131 C13 C13A C17A . . . . 119.92(11) ?
C12 C13 C13A C17A . . . . -0.11(12) ?
C17A C13A C14 C15 . . . . -0.45(18) ?
C13 C13A C14 C15 . . . . -179.34(12) ?
C13A C14 C15 C16 . . . . -0.27(19) ?
C14 C15 C16 C17 . . . . 0.6(2) ?
C15 C16 C17 C17A . . . . -0.26(19) ?
C16 C17 C17A C13A . . . . -0.47(18) ?
C16 C17 C17A N11 . . . . 178.49(11) ?
C14 C13A C17A C17 . . . . 0.84(18) ?
C13 C13A C17A C17 . . . . 179.94(11) ?
C14 C13A C17A N11 . . . . -178.29(11) ?
C13 C13A C17A N11 . . . . 0.80(13) ?
C12 N11 C17A C17 . . . . 179.67(12) ?
C11 N11 C17A C17 . . . . 9.12(19) ?
C12 N11 C17A C13A . . . . -1.27(14) ?
C11 N11 C17A C13A . . . . -171.81(11) ?
C12 N11 C11 C111 . . . . 119.11(13) ?
C17A N11 C11 C111 . . . . -71.60(15) ?
N11 C11 C111 C112 . . . . -54.19(16) ?
N11 C11 C111 C116 . . . . 128.16(12) ?
C116 C111 C112 C113 . . . . 0.3(2) ?
C11 C111 C112 C113 . . . . -177.40(12) ?
C111 C112 C113 C114 . . . . 0.4(2) ?
C112 C113 C114 C115 . . . . -0.5(2) ?
C113 C114 C115 C116 . . . . -0.2(2) ?
C114 C115 C116 C111 . . . . 0.8(2) ?
C112 C111 C116 C115 . . . . -0.9(2) ?
C11 C111 C116 C115 . . . . 176.81(12) ?
O13 C13 C131 C132 . . . . 172.21(9) ?
C13A C13 C131 C132 . . . . -63.91(13) ?
C12 C13 C131 C132 . . . . 50.92(13) ?
C13 C131 C132 O132 . . . . 4.93(16) ?
C13 C131 C132 C145 . . . . -174.30(10) ?
C18A O141 C142 O143 . . . . 2.44(16) ?
O141 C142 O143 C14A . . . . -2.36(15) ?
C142 O143 C14A C144 . . . . -178.25(14) ?
C142 O143 C14A C18A . . . . 1.39(15) ?
O143 C14A C144 C145 . . . . 179.07(12) ?
C18A C14A C144 C145 . . . . -0.52(19) ?
C14A C144 C145 C146 . . . . 0.32(17) ?
C14A C144 C145 C132 . . . . -179.53(11) ?
O132 C132 C145 C146 . . . . 177.53(11) ?
C131 C132 C145 C146 . . . . -3.24(16) ?
O132 C132 C145 C144 . . . . -2.62(17) ?
C131 C132 C145 C144 . . . . 176.61(10) ?
C144 C145 C146 C147 . . . . 0.00(19) ?
C132 C145 C146 C147 . . . . 179.85(11) ?
C145 C146 C147 C18A . . . . -0.13(19) ?
C142 O141 C18A C147 . . . . 177.74(14) ?
C142 O141 C18A C14A . . . . -1.60(15) ?
C146 C147 C18A O141 . . . . -179.34(13) ?
C146 C147 C18A C14A . . . . -0.1(2) ?
C144 C14A C18A O141 . . . . 179.80(12) ?
O143 C14A C18A O141 . . . . 0.14(16) ?
C144 C14A C18A C147 . . . . 0.4(2) ?
O143 C14A C18A C147 . . . . -179.24(12) ?
C27A N21 C22 O22 . . . . -179.43(11) ?
C21 N21 C22 O22 . . . . -4.74(19) ?
C27A N21 C22 C23 . . . . 2.74(13) ?
C21 N21 C22 C23 . . . . 177.43(10) ?
O22 C22 C23 O23 . . . . -65.20(14) ?
N21 C22 C23 O23 . . . . 112.66(11) ?
O22 C22 C23 C23A . . . . 179.92(11) ?
N21 C22 C23 C23A . . . . -2.23(12) ?
O22 C22 C23 C231 . . . . 56.11(15) ?
N21 C22 C23 C231 . . . . -126.04(10) ?
O23 C23 C23A C24 . . . . 66.66(16) ?
C231 C23 C23A C24 . . . . -57.91(17) ?
C22 C23 C23A C24 . . . . -178.88(12) ?
O23 C23 C23A C27A . . . . -113.52(11) ?
C231 C23 C23A C27A . . . . 121.91(11) ?
C22 C23 C23A C27A . . . . 0.94(12) ?
C27A C23A C24 C25 . . . . -1.35(18) ?
C23 C23A C24 C25 . . . . 178.45(12) ?
C23A C24 C25 C26 . . . . 0.07(19) ?
C24 C25 C26 C27 . . . . 1.6(2) ?
C25 C26 C27 C27A . . . . -1.8(2) ?
C26 C27 C27A C23A . . . . 0.54(19) ?
C26 C27 C27A N21 . . . . -178.70(12) ?
C24 C23A C27A C27 . . . . 1.06(19) ?
C23 C23A C27A C27 . . . . -178.78(11) ?
C24 C23A C27A N21 . . . . -179.58(11) ?
C23 C23A C27A N21 . . . . 0.58(13) ?
C22 N21 C27A C27 . . . . 177.17(12) ?
C21 N21 C27A C27 . . . . 2.6(2) ?
C22 N21 C27A C23A . . . . -2.14(14) ?
C21 N21 C27A C23A . . . . -176.75(11) ?
C22 N21 C21 C211 . . . . 108.60(13) ?
C27A N21 C21 C211 . . . . -77.47(15) ?
N21 C21 C211 C212 . . . . -27.57(17) ?
N21 C21 C211 C216 . . . . 155.57(11) ?
C216 C211 C212 C213 . . . . -0.2(2) ?
C21 C211 C212 C213 . . . . -177.07(13) ?
C211 C212 C213 C214 . . . . 0.5(2) ?
C212 C213 C214 C215 . . . . -0.5(2) ?
C213 C214 C215 C216 . . . . 0.2(2) ?
C214 C215 C216 C211 . . . . 0.1(2) ?
C212 C211 C216 C215 . . . . -0.1(2) ?
C21 C211 C216 C215 . . . . 176.90(12) ?
O23 C23 C231 C232 . . . . 172.42(9) ?
C23A C23 C231 C232 . . . . -63.42(13) ?
C22 C23 C231 C232 . . . . 51.93(13) ?
C23 C231 C232 O232 . . . . 4.98(16) ?
C23 C231 C232 C245 . . . . -174.80(10) ?
C28A O241 C242 O243 . . . . 7.40(17) ?
O241 C242 O243 C24A . . . . -7.49(17) ?
C242 O243 C24A C244 . . . . -177.11(15) ?
C242 O243 C24A C28A . . . . 4.78(17) ?
O243 C24A C244 C245 . . . . -178.62(14) ?
C28A C24A C244 C245 . . . . -0.7(2) ?
C24A C244 C245 C246 . . . . -0.24(19) ?
C24A C244 C245 C232 . . . . 179.15(12) ?
O232 C232 C245 C246 . . . . 178.27(12) ?
C231 C232 C245 C246 . . . . -1.95(17) ?
O232 C232 C245 C244 . . . . -1.13(18) ?
C231 C232 C245 C244 . . . . 178.65(11) ?
C244 C245 C246 C247 . . . . 0.9(2) ?
C232 C245 C246 C247 . . . . -178.52(12) ?
C245 C246 C247 C28A . . . . -0.5(2) ?
C242 O241 C28A C247 . . . . 176.00(15) ?
C242 O241 C28A C24A . . . . -4.52(16) ?
C246 C247 C28A O241 . . . . 178.93(14) ?
C246 C247 C28A C24A . . . . -0.5(2) ?
C244 C24A C28A O241 . . . . -178.39(13) ?
O243 C24A C28A O241 . . . . -0.14(17) ?
C244 C24A C28A C247 . . . . 1.1(2) ?
O243 C24A C28A C247 . . . . 179.37(14) ?

_cod_database_fobs_code 2022152
