#------------------------------------------------------------------------------
#$Date: 2022-06-11 04:51:51 +0300 (Sat, 11 Jun 2022) $
#$Revision: 275971 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244115.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_2244115
loop_
_publ_author_name
'Li, Chun'
'Weaver, Matthew J.'
'Campbell, Michael J.'
'Natale, Nicholas R.'
_publ_section_title
;
 Syntheses and crystal structures of a nitro--anthracene--isoxazole and
 its oxidation product
;
_journal_coeditor_code           HB8020
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022005710
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C21 H16 N2 O5'
_chemical_formula_moiety         'C21 H16 N2 O5'
_chemical_formula_sum            'C21 H16 N2 O5'
_chemical_formula_weight         376.36
_chemical_name_systematic
;
Ethyl
5-methyl-3-(10-nitroanthracen-9-yl)isoxazole-4-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.879(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.4968(10)
_cell_length_b                   14.8697(9)
_cell_length_c                   16.1836(9)
_cell_measurement_reflns_used    7597
_cell_measurement_temperature    99.9
_cell_measurement_theta_max      20.97
_cell_measurement_theta_min      2.69
_cell_volume                     3601.5(4)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX2 (Bruker, 2012)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/1 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS  (Sheldrick, 2008)
;
_diffrn_ambient_temperature      99.9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.722
_diffrn_reflns_theta_min         2.691
_diffrn_source                   '2 kW sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.244
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.190
_refine_ls_abs_structure_details
;
Flack x determined using 2257 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     546
_refine_ls_number_reflns         7615
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0587
_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)+(0.0864P)²+2.3310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1584
_reflns_number_gt                5596
_reflns_number_total             7615
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb8020sup1.cif
_cod_data_source_block           I
_cod_database_code               2244115
_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   0.971
_shelx_estimated_absorpt_t_max   0.978
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
O O1 0.3319(3) 0.2201(3) 0.5466(2) 0.0487(9) Uani d 1 . .
O O2 0.3808(2) 0.0465(3) 0.3397(2) 0.0459(9) Uani d 1 . .
O O3 0.4880(2) 0.0385(3) 0.4815(2) 0.0471(9) Uani d 1 . .
N N1 0.2636(3) 0.2332(3) 0.4569(3) 0.0440(10) Uani d 1 . .
C C1 0.3269(3) 0.2892(3) 0.2833(4) 0.0392(11) Uani d 1 . .
H H1 0.363669 0.290494 0.346904 0.047 Uiso calc 1 . .
C C2 0.3469(4) 0.3427(4) 0.2259(4) 0.0519(14) Uani d 1 . .
H H2 0.397851 0.380760 0.250073 0.062 Uiso calc 1 . .
C C3 0.2934(4) 0.3424(4) 0.1320(4) 0.0548(15) Uani d 1 . .
H H3 0.308016 0.380624 0.093210 0.066 Uiso calc 1 . .
C C4 0.2203(4) 0.2876(4) 0.0955(4) 0.0471(13) Uani d 1 . .
H H4 0.184644 0.288156 0.031651 0.056 Uiso calc 1 . .
C C5 0.0334(3) 0.0476(3) 0.1397(3) 0.0375(11) Uani d 1 . .
H H5 0.001(4) 0.040(3) 0.083(4) 0.045(15) Uiso d 1 . .
C C6 0.0166(4) -0.0086(4) 0.1956(4) 0.0447(13) Uani d 1 . .
H H6 -0.030(4) -0.042(4) 0.171(4) 0.042(15) Uiso d 1 . .
C C7 0.0677(3) -0.0057(4) 0.2910(3) 0.0433(12) Uani d 1 . .
H H7 0.054540 -0.045527 0.329570 0.052 Uiso calc 1 . .
C C8 0.1361(3) 0.0548(3) 0.3273(3) 0.0363(11) Uani d 1 . .
H H8 0.170089 0.056581 0.391448 0.044 Uiso calc 1 . .
C C9 0.2294(3) 0.1746(3) 0.3054(3) 0.0335(10) Uani d 1 . .
C C10 0.1272(3) 0.1697(3) 0.1202(3) 0.0359(11) Uani d 1 . .
C C11 0.1972(3) 0.2301(3) 0.1519(3) 0.0354(11) Uani d 1 . .
C C12 0.2511(3) 0.2315(3) 0.2482(3) 0.0326(10) Uani d 1 . .
C C13 0.1573(3) 0.1148(3) 0.2714(3) 0.0295(10) Uani d 1 . .
C C14 0.1042(3) 0.1105(3) 0.1749(3) 0.0325(10) Uani d 1 . .
C C15 0.2857(3) 0.1785(3) 0.4056(3) 0.0330(10) Uani d 1 . .
C C16 0.3647(3) 0.1298(3) 0.4562(3) 0.0353(10) Uani d 1 . .
C C17 0.3904(3) 0.1590(4) 0.5441(3) 0.0404(12) Uani d 1 . .
C C18 0.4659(4) 0.1363(4) 0.6323(3) 0.0537(15) Uani d 1 . .
H H18A 0.516186 0.176866 0.642774 0.081 Uiso calc 1 . .
H H18B 0.484587 0.074058 0.630503 0.081 Uiso calc 1 . .
H H18C 0.446894 0.143120 0.681695 0.081 Uiso calc 1 . .
C C19 0.4107(3) 0.0671(4) 0.4186(3) 0.0402(12) Uani d 1 . .
C C20 0.5375(4) -0.0214(4) 0.4483(4) 0.0517(14) Uani d 1 . .
H H20A 0.556563 0.011073 0.406087 0.062 Uiso calc 1 . .
H H20B 0.499576 -0.072871 0.415356 0.062 Uiso calc 1 . .
C C21 0.6175(4) -0.0541(4) 0.5297(4) 0.0585(15) Uani d 1 . .
H H21A 0.651142 -0.096711 0.509947 0.088 Uiso calc 1 . .
H H21B 0.597864 -0.083994 0.572036 0.088 Uiso calc 1 . .
H H21C 0.655804 -0.002855 0.560146 0.088 Uiso calc 1 . .
O O4 0.1027(18) 0.111(3) -0.022(3) 0.072(6) Uani d 0.572(13) A 1
O O5 -0.0003(7) 0.1959(10) -0.0102(7) 0.068(3) Uani d 0.572(13) A 1
N N2 0.076(3) 0.156(2) 0.025(3) 0.039(4) Uani d 0.572(13) A 1
O O4A 0.073(3) 0.105(4) -0.022(4) 0.072(6) Uani d 0.428(13) A 2
O O5A 0.0259(10) 0.2395(14) -0.0113(10) 0.068(3) Uani d 0.428(13) A 2
N N2A 0.066(4) 0.178(3) 0.017(4) 0.039(4) Uani d 0.428(13) A 2
O O6 0.4350(3) 0.7239(3) 0.2788(2) 0.0553(11) Uani d 1 . .
O O7 0.3756(2) 0.5736(2) 0.4917(2) 0.0424(8) Uani d 1 . .
O O8 0.2920(2) 0.5316(2) 0.3474(2) 0.0422(8) Uani d 1 . .
N N3 0.4850(3) 0.7577(3) 0.3678(3) 0.0561(13) Uani d 1 . .
N N4 0.6061(3) 0.7796(3) 0.8043(3) 0.0495(12) Uani d 1 . .
C C22 0.3713(4) 0.8310(4) 0.4975(4) 0.0506(14) Uani d 1 . .
H H22 0.347573 0.821907 0.433552 0.061 Uiso calc 1 . .
C C23 0.3270(4) 0.8841(4) 0.5326(4) 0.0600(16) Uani d 1 . .
H H23 0.272392 0.911450 0.492941 0.072 Uiso calc 1 . .
C C24 0.3606(4) 0.8994(4) 0.6269(4) 0.0568(15) Uani d 1 . .
H H24 0.328476 0.936589 0.650609 0.068 Uiso calc 1 . .
C C25 0.4393(4) 0.8609(3) 0.6845(4) 0.0506(14) Uani d 1 . .
H H25 0.461760 0.872032 0.748095 0.061 Uiso calc 1 . .
C C26 0.6969(3) 0.6606(4) 0.7304(3) 0.0471(13) Uani d 1 . .
H H26 0.721891 0.669551 0.794480 0.057 Uiso calc 1 . .
C C27 0.7377(4) 0.6055(5) 0.6938(5) 0.0650(17) Uani d 1 . .
H H27 0.792063 0.577059 0.732452 0.078 Uiso calc 1 . .
C C28 0.7018(4) 0.5891(5) 0.6000(4) 0.0635(17) Uani d 1 . .
H H28 0.731967 0.549990 0.575834 0.076 Uiso calc 1 . .
C C29 0.6250(4) 0.6284(4) 0.5438(4) 0.0481(13) Uani d 1 . .
H H29 0.600529 0.615429 0.480499 0.058 Uiso calc 1 . .
C C30 0.4988(4) 0.7306(4) 0.5209(3) 0.0405(12) Uani d 1 . .
C C31 0.5696(3) 0.7629(3) 0.7055(3) 0.0364(11) Uani d 1 . .
C C32 0.4875(3) 0.8051(3) 0.6514(3) 0.0381(11) Uani d 1 . .
C C33 0.4527(3) 0.7886(3) 0.5551(3) 0.0400(12) Uani d 1 . .
C C34 0.5802(3) 0.6883(3) 0.5776(3) 0.0349(11) Uani d 1 . .
C C35 0.6165(3) 0.7057(3) 0.6735(3) 0.0369(11) Uani d 1 . .
C C36 0.4597(4) 0.7112(3) 0.4208(3) 0.0413(12) Uani d 1 . .
C C37 0.3956(3) 0.6454(3) 0.3713(3) 0.0370(11) Uani d 1 . .
C C38 0.3817(3) 0.6569(4) 0.2828(3) 0.0429(12) Uani d 1 . .
C C39 0.3211(4) 0.6178(4) 0.1946(3) 0.0478(13) Uani d 1 . .
H H39A 0.316485 0.552762 0.201431 0.072 Uiso calc 1 . .
H H39B 0.344798 0.629473 0.149346 0.072 Uiso calc 1 . .
H H39C 0.261828 0.645184 0.174453 0.072 Uiso calc 1 . .
C C40 0.3545(3) 0.5804(3) 0.4101(3) 0.0365(11) Uani d 1 . .
C C41 0.2435(4) 0.4683(4) 0.3801(4) 0.0487(13) Uani d 1 . .
H H41A 0.226101 0.498471 0.424769 0.058 Uiso calc 1 . .
H H41B 0.282252 0.416477 0.410479 0.058 Uiso calc 1 . .
C C42 0.1625(4) 0.4370(4) 0.3006(4) 0.0563(15) Uani d 1 . .
H H42A 0.180119 0.410741 0.255014 0.084 Uiso calc 1 . .
H H42B 0.122459 0.488051 0.273756 0.084 Uiso calc 1 . .
H H42C 0.131623 0.391508 0.320559 0.084 Uiso calc 1 . .
O O9 0.5612(9) 0.7525(10) 0.8442(5) 0.075(5) Uani d 0.64(3) B 1
O O10 0.6744(11) 0.8219(11) 0.8389(6) 0.076(4) Uani d 0.64(3) B 1
O O9A 0.6187(17) 0.7124(9) 0.8578(8) 0.060(6) Uani d 0.36(3) B 2
O O10A 0.6276(15) 0.8540(10) 0.8356(9) 0.054(5) Uani d 0.36(3) B 2
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 2.00 -1.00 0.0580
0.00 -2.00 1.00 0.1490
2.00 1.00 0.00 0.0990
-2.00 -1.00 0.00 0.1110
1.00 0.00 0.00 0.1220
-1.00 0.00 0.00 0.0750
-2.00 -1.00 1.00 0.1060
2.00 1.00 -1.00 0.0970
-1.00 0.00 1.00 0.0940
1.00 0.00 -1.00 0.0940
-1.00 2.00 1.00 0.0130
1.00 -2.00 -1.00 0.1220
-1.00 1.00 2.00 0.0420
1.00 -1.00 -2.00 0.1420
0.00 -2.00 -1.00 0.1220
0.00 2.00 1.00 0.0030
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
C17 O1 N1 . . 109.5(3) ?
C19 O3 C20 . . 114.9(4) ?
C15 N1 O1 . . 104.3(4) ?
C2 C1 H1 . . 119.9 ?
C2 C1 C12 . . 120.2(5) ?
C12 C1 H1 . . 119.9 ?
C1 C2 H2 . . 119.5 ?
C1 C2 C3 . . 120.9(5) ?
C3 C2 H2 . . 119.5 ?
C2 C3 H3 . . 119.7 ?
C4 C3 C2 . . 120.6(5) ?
C4 C3 H3 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C3 C4 C11 . . 120.7(5) ?
C11 C4 H4 . . 119.7 ?
C6 C5 H5 . . 115(4) ?
C6 C5 C14 . . 120.7(5) ?
C14 C5 H5 . . 124(4) ?
C5 C6 H6 . . 116(4) ?
C5 C6 C7 . . 121.2(5) ?
C7 C6 H6 . . 122(4) ?
C6 C7 H7 . . 120.2 ?
C8 C7 C6 . . 119.6(5) ?
C8 C7 H7 . . 120.2 ?
C7 C8 H8 . . 119.3 ?
C7 C8 C13 . . 121.4(4) ?
C13 C8 H8 . . 119.3 ?
C12 C9 C15 . . 118.5(4) ?
C13 C9 C12 . . 122.2(4) ?
C13 C9 C15 . . 119.3(4) ?
C11 C10 C14 . . 125.3(4) ?
C11 C10 N2 . . 121.3(18) ?
C11 C10 N2A . . 115(2) ?
C14 C10 N2 . . 113.2(17) ?
C14 C10 N2A . . 120(2) ?
C4 C11 C12 . . 118.7(4) ?
C10 C11 C4 . . 124.3(4) ?
C10 C11 C12 . . 117.0(4) ?
C1 C12 C11 . . 118.9(4) ?
C9 C12 C1 . . 121.6(4) ?
C9 C12 C11 . . 119.5(4) ?
C8 C13 C14 . . 117.8(4) ?
C9 C13 C8 . . 123.2(4) ?
C9 C13 C14 . . 119.0(4) ?
C5 C14 C13 . . 119.3(4) ?
C10 C14 C5 . . 123.7(4) ?
C10 C14 C13 . . 117.0(4) ?
N1 C15 C9 . . 119.8(4) ?
N1 C15 C16 . . 112.6(4) ?
C16 C15 C9 . . 127.6(4) ?
C15 C16 C19 . . 126.2(4) ?
C17 C16 C15 . . 104.2(4) ?
C17 C16 C19 . . 129.4(4) ?
O1 C17 C16 . . 109.5(4) ?
O1 C17 C18 . . 116.7(4) ?
C16 C17 C18 . . 133.8(5) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18B . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O2 C19 O3 . . 124.6(5) ?
O2 C19 C16 . . 123.0(5) ?
O3 C19 C16 . . 112.3(4) ?
O3 C20 H20A . . 110.3 ?
O3 C20 H20B . . 110.3 ?
O3 C20 C21 . . 107.3(5) ?
H20A C20 H20B . . 108.5 ?
C21 C20 H20A . . 110.3 ?
C21 C20 H20B . . 110.3 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21B . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O4 N2 C10 . . 123(3) ?
O4 N2 O5 . . 122(4) ?
O5 N2 C10 . . 116(3) ?
O4A N2A C10 . . 108(3) ?
O5A N2A C10 . . 121(5) ?
O5A N2A O4A . . 131(6) ?
C38 O6 N3 . . 109.0(4) ?
C40 O8 C41 . . 116.3(4) ?
C36 N3 O6 . . 105.7(4) ?
O9 N4 C31 . . 116.7(5) ?
O10 N4 C31 . . 118.0(6) ?
O10 N4 O9 . . 125.2(7) ?
O9A N4 C31 . . 118.6(6) ?
O10A N4 C31 . . 121.6(8) ?
O10A N4 O9A . . 119.7(9) ?
C23 C22 H22 . . 119.6 ?
C23 C22 C33 . . 120.9(5) ?
C33 C22 H22 . . 119.6 ?
C22 C23 H23 . . 119.5 ?
C22 C23 C24 . . 121.0(5) ?
C24 C23 H23 . . 119.5 ?
C23 C24 H24 . . 120.0 ?
C25 C24 C23 . . 120.0(6) ?
C25 C24 H24 . . 120.0 ?
C24 C25 H25 . . 119.4 ?
C24 C25 C32 . . 121.1(5) ?
C32 C25 H25 . . 119.4 ?
C27 C26 H26 . . 119.9 ?
C27 C26 C35 . . 120.2(5) ?
C35 C26 H26 . . 119.9 ?
C26 C27 H27 . . 119.3 ?
C26 C27 C28 . . 121.5(5) ?
C28 C27 H27 . . 119.3 ?
C27 C28 H28 . . 119.8 ?
C29 C28 C27 . . 120.4(6) ?
C29 C28 H28 . . 119.8 ?
C28 C29 H29 . . 119.6 ?
C28 C29 C34 . . 120.9(5) ?
C34 C29 H29 . . 119.6 ?
C33 C30 C34 . . 122.7(4) ?
C33 C30 C36 . . 119.0(5) ?
C34 C30 C36 . . 118.3(5) ?
C32 C31 N4 . . 116.4(4) ?
C35 C31 N4 . . 118.1(4) ?
C35 C31 C32 . . 125.5(4) ?
C25 C32 C31 . . 125.2(5) ?
C25 C32 C33 . . 118.9(5) ?
C31 C32 C33 . . 115.9(5) ?
C22 C33 C32 . . 118.1(5) ?
C30 C33 C22 . . 122.2(5) ?
C30 C33 C32 . . 119.7(5) ?
C29 C34 C30 . . 122.7(4) ?
C29 C34 C35 . . 119.1(4) ?
C30 C34 C35 . . 118.2(5) ?
C26 C35 C34 . . 117.8(5) ?
C31 C35 C26 . . 124.1(4) ?
C31 C35 C34 . . 118.0(4) ?
N3 C36 C30 . . 119.9(5) ?
N3 C36 C37 . . 111.5(4) ?
C37 C36 C30 . . 128.6(5) ?
C36 C37 C40 . . 125.7(4) ?
C38 C37 C36 . . 105.3(5) ?
C38 C37 C40 . . 129.0(5) ?
O6 C38 C37 . . 108.6(4) ?
O6 C38 C39 . . 115.7(4) ?
C37 C38 C39 . . 135.6(5) ?
C38 C39 H39A . . 109.5 ?
C38 C39 H39B . . 109.5 ?
C38 C39 H39C . . 109.5 ?
H39A C39 H39B . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
O7 C40 O8 . . 124.2(5) ?
O7 C40 C37 . . 123.0(5) ?
O8 C40 C37 . . 112.7(4) ?
O8 C41 H41A . . 110.0 ?
O8 C41 H41B . . 110.0 ?
O8 C41 C42 . . 108.4(5) ?
H41A C41 H41B . . 108.4 ?
C42 C41 H41A . . 110.0 ?
C42 C41 H41B . . 110.0 ?
C41 C42 H42A . . 109.5 ?
C41 C42 H42B . . 109.5 ?
C41 C42 H42C . . 109.5 ?
H42A C42 H42B . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
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
O1 N1 . 1.428(5) ?
O1 C17 . 1.338(7) ?
O2 C19 . 1.199(6) ?
O3 C19 . 1.324(6) ?
O3 C20 . 1.455(7) ?
N1 C15 . 1.318(6) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.365(7) ?
C1 C12 . 1.423(7) ?
C2 H2 . 0.9500 ?
C2 C3 . 1.401(8) ?
C3 H3 . 0.9500 ?
C3 C4 . 1.366(8) ?
C4 H4 . 0.9500 ?
C4 C11 . 1.416(7) ?
C5 H5 . 0.86(6) ?
C5 C6 . 1.343(7) ?
C5 C14 . 1.416(7) ?
C6 H6 . 0.85(6) ?
C6 C7 . 1.415(7) ?
C7 H7 . 0.9500 ?
C7 C8 . 1.367(7) ?
C8 H8 . 0.9500 ?
C8 C13 . 1.415(6) ?
C9 C12 . 1.408(7) ?
C9 C13 . 1.399(6) ?
C9 C15 . 1.493(6) ?
C10 C11 . 1.380(7) ?
C10 C14 . 1.407(7) ?
C10 N2 . 1.43(5) ?
C10 N2A . 1.55(6) ?
C11 C12 . 1.433(6) ?
C13 C14 . 1.436(6) ?
C15 C16 . 1.413(7) ?
C16 C17 . 1.373(7) ?
C16 C19 . 1.485(7) ?
C17 C18 . 1.485(7) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C20 C21 . 1.500(8) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
O4 N2 . 1.22(6) ?
O5 N2 . 1.29(4) ?
O4A N2A . 1.27(9) ?
O5A N2A . 1.11(4) ?
O6 N3 . 1.418(6) ?
O6 C38 . 1.349(7) ?
O7 C40 . 1.219(6) ?
O8 C40 . 1.319(6) ?
O8 C41 . 1.470(6) ?
N3 C36 . 1.301(7) ?
N4 C31 . 1.474(6) ?
N4 O9 . 1.237(9) ?
N4 O10 . 1.203(11) ?
N4 O9A . 1.281(13) ?
N4 O10A . 1.206(14) ?
C22 H22 . 0.9500 ?
C22 C23 . 1.352(8) ?
C22 C33 . 1.420(8) ?
C23 H23 . 0.9500 ?
C23 C24 . 1.406(9) ?
C24 H24 . 0.9500 ?
C24 C25 . 1.366(9) ?
C25 H25 . 0.9500 ?
C25 C32 . 1.403(8) ?
C26 H26 . 0.9500 ?
C26 C27 . 1.346(9) ?
C26 C35 . 1.425(7) ?
C27 H27 . 0.9500 ?
C27 C28 . 1.399(9) ?
C28 H28 . 0.9500 ?
C28 C29 . 1.343(8) ?
C29 H29 . 0.9500 ?
C29 C34 . 1.406(7) ?
C30 C33 . 1.408(8) ?
C30 C34 . 1.416(7) ?
C30 C36 . 1.498(7) ?
C31 C32 . 1.413(7) ?
C31 C35 . 1.388(7) ?
C32 C33 . 1.438(7) ?
C34 C35 . 1.433(7) ?
C36 C37 . 1.415(7) ?
C37 C38 . 1.362(7) ?
C37 C40 . 1.465(7) ?
C38 C39 . 1.474(7) ?
C39 H39A . 0.9800 ?
C39 H39B . 0.9800 ?
C39 H39C . 0.9800 ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C41 C42 . 1.488(8) ?
C42 H42A . 0.9800 ?
C42 H42B . 0.9800 ?
C42 H42C . 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
C1 H1 O5 4 0.95 2.46 3.366(12) 159 yes
C3 H3 O7 2_564 0.95 2.44 3.339(6) 158 yes
C7 H7 O4 2 0.95 2.40 3.24(4) 147 yes
C7 H7 O4A 2 0.95 2.46 3.34(6) 154 yes
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
O1 N1 C15 C9 . . . . -179.2(4) ?
O1 N1 C15 C16 . . . . 0.1(5) ?
N1 O1 C17 C16 . . . . -0.1(6) ?
N1 O1 C17 C18 . . . . -179.4(5) ?
N1 C15 C16 C17 . . . . -0.1(6) ?
N1 C15 C16 C19 . . . . -176.0(5) ?
C1 C2 C3 C4 . . . . -0.7(9) ?
C2 C1 C12 C9 . . . . 179.1(5) ?
C2 C1 C12 C11 . . . . 0.6(7) ?
C2 C3 C4 C11 . . . . 0.0(9) ?
C3 C4 C11 C10 . . . . -176.7(5) ?
C3 C4 C11 C12 . . . . 1.0(8) ?
C4 C11 C12 C1 . . . . -1.2(7) ?
C4 C11 C12 C9 . . . . -179.8(5) ?
C5 C6 C7 C8 . . . . -0.6(8) ?
C6 C5 C14 C10 . . . . 178.2(5) ?
C6 C5 C14 C13 . . . . -1.0(7) ?
C6 C7 C8 C13 . . . . -0.2(8) ?
C7 C8 C13 C9 . . . . -176.8(5) ?
C7 C8 C13 C14 . . . . 0.3(7) ?
C8 C13 C14 C5 . . . . 0.2(6) ?
C8 C13 C14 C10 . . . . -179.0(4) ?
C9 C13 C14 C5 . . . . 177.5(4) ?
C9 C13 C14 C10 . . . . -1.7(6) ?
C9 C15 C16 C17 . . . . 179.1(5) ?
C9 C15 C16 C19 . . . . 3.2(8) ?
C10 C11 C12 C1 . . . . 176.6(5) ?
C10 C11 C12 C9 . . . . -2.0(7) ?
C11 C10 C14 C5 . . . . -178.2(5) ?
C11 C10 C14 C13 . . . . 1.0(7) ?
C11 C10 N2 O4 . . . . 77(4) ?
C11 C10 N2 O5 . . . . -101(3) ?
C11 C10 N2A O4A . . . . 115(4) ?
C11 C10 N2A O5A . . . . -64(6) ?
C12 C1 C2 C3 . . . . 0.4(9) ?
C12 C9 C13 C8 . . . . 177.7(4) ?
C12 C9 C13 C14 . . . . 0.7(7) ?
C12 C9 C15 N1 . . . . 91.6(6) ?
C12 C9 C15 C16 . . . . -87.6(6) ?
C13 C9 C12 C1 . . . . -177.3(5) ?
C13 C9 C12 C11 . . . . 1.3(7) ?
C13 C9 C15 N1 . . . . -88.6(6) ?
C13 C9 C15 C16 . . . . 92.3(6) ?
C14 C5 C6 C7 . . . . 1.2(8) ?
C14 C10 C11 C4 . . . . 178.5(5) ?
C14 C10 C11 C12 . . . . 0.8(7) ?
C14 C10 N2 O4 . . . . -97(4) ?
C14 C10 N2 O5 . . . . 85(3) ?
C14 C10 N2A O4A . . . . -71(5) ?
C14 C10 N2A O5A . . . . 110(5) ?
C15 C9 C12 C1 . . . . 2.6(7) ?
C15 C9 C12 C11 . . . . -178.9(4) ?
C15 C9 C13 C8 . . . . -2.1(7) ?
C15 C9 C13 C14 . . . . -179.2(4) ?
C15 C16 C17 O1 . . . . 0.1(5) ?
C15 C16 C17 C18 . . . . 179.3(6) ?
C15 C16 C19 O2 . . . . -5.4(8) ?
C15 C16 C19 O3 . . . . 173.5(4) ?
C17 O1 N1 C15 . . . . 0.0(5) ?
C17 C16 C19 O2 . . . . 179.8(5) ?
C17 C16 C19 O3 . . . . -1.2(7) ?
C19 O3 C20 C21 . . . . -174.3(5) ?
C19 C16 C17 O1 . . . . 175.8(5) ?
C19 C16 C17 C18 . . . . -5.1(10) ?
C20 O3 C19 O2 . . . . 0.5(7) ?
C20 O3 C19 C16 . . . . -178.4(4) ?
N2 C10 C11 C4 . . . . 4.9(18) ?
N2 C10 C11 C12 . . . . -172.8(17) ?
N2 C10 C14 C5 . . . . -4.1(18) ?
N2 C10 C14 C13 . . . . 175.1(17) ?
N2A C10 C11 C4 . . . . -8(3) ?
N2A C10 C11 C12 . . . . 174(2) ?
N2A C10 C14 C5 . . . . 9(3) ?
N2A C10 C14 C13 . . . . -172(2) ?
O6 N3 C36 C30 . . . . -179.1(5) ?
O6 N3 C36 C37 . . . . 1.3(6) ?
N3 O6 C38 C37 . . . . -0.5(6) ?
N3 O6 C38 C39 . . . . 176.6(5) ?
N3 C36 C37 C38 . . . . -1.6(6) ?
N3 C36 C37 C40 . . . . 178.6(5) ?
N4 C31 C32 C25 . . . . 0.1(7) ?
N4 C31 C32 C33 . . . . 179.7(4) ?
N4 C31 C35 C26 . . . . 1.3(7) ?
N4 C31 C35 C34 . . . . 179.0(4) ?
C22 C23 C24 C25 . . . . 0.4(10) ?
C23 C22 C33 C30 . . . . 177.8(6) ?
C23 C22 C33 C32 . . . . -1.1(8) ?
C23 C24 C25 C32 . . . . -0.6(9) ?
C24 C25 C32 C31 . . . . 179.5(5) ?
C24 C25 C32 C33 . . . . -0.1(8) ?
C25 C32 C33 C22 . . . . 0.9(7) ?
C25 C32 C33 C30 . . . . -178.0(5) ?
C26 C27 C28 C29 . . . . -0.1(11) ?
C27 C26 C35 C31 . . . . 179.3(5) ?
C27 C26 C35 C34 . . . . 1.6(8) ?
C27 C28 C29 C34 . . . . 1.6(10) ?
C28 C29 C34 C30 . . . . -179.5(5) ?
C28 C29 C34 C35 . . . . -1.5(8) ?
C29 C34 C35 C26 . . . . -0.1(7) ?
C29 C34 C35 C31 . . . . -177.9(4) ?
C30 C34 C35 C26 . . . . 178.0(4) ?
C30 C34 C35 C31 . . . . 0.1(6) ?
C30 C36 C37 C38 . . . . 178.9(5) ?
C30 C36 C37 C40 . . . . -0.9(9) ?
C31 C32 C33 C22 . . . . -178.7(5) ?
C31 C32 C33 C30 . . . . 2.3(7) ?
C32 C31 C35 C26 . . . . -176.7(5) ?
C32 C31 C35 C34 . . . . 0.9(7) ?
C33 C22 C23 C24 . . . . 0.5(10) ?
C33 C30 C34 C29 . . . . 178.1(5) ?
C33 C30 C34 C35 . . . . 0.1(7) ?
C33 C30 C36 N3 . . . . 95.1(7) ?
C33 C30 C36 C37 . . . . -85.4(7) ?
C34 C30 C33 C22 . . . . 179.7(5) ?
C34 C30 C33 C32 . . . . -1.4(8) ?
C34 C30 C36 N3 . . . . -85.9(6) ?
C34 C30 C36 C37 . . . . 93.6(7) ?
C35 C26 C27 C28 . . . . -1.5(10) ?
C35 C31 C32 C25 . . . . 178.2(5) ?
C35 C31 C32 C33 . . . . -2.2(7) ?
C36 C30 C33 C22 . . . . -1.4(8) ?
C36 C30 C33 C32 . . . . 177.5(4) ?
C36 C30 C34 C29 . . . . -0.8(7) ?
C36 C30 C34 C35 . . . . -178.8(4) ?
C36 C37 C38 O6 . . . . 1.2(6) ?
C36 C37 C38 C39 . . . . -175.0(6) ?
C36 C37 C40 O7 . . . . -3.9(8) ?
C36 C37 C40 O8 . . . . 175.1(5) ?
C38 O6 N3 C36 . . . . -0.5(6) ?
C38 C37 C40 O7 . . . . 176.3(5) ?
C38 C37 C40 O8 . . . . -4.6(7) ?
C40 O8 C41 C42 . . . . 166.0(4) ?
C40 C37 C38 O6 . . . . -179.0(5) ?
C40 C37 C38 C39 . . . . 4.7(10) ?
C41 O8 C40 O7 . . . . 2.6(7) ?
C41 O8 C40 C37 . . . . -176.5(4) ?
O9 N4 C31 C32 . . . . 63.2(11) ?
O9 N4 C31 C35 . . . . -115.0(11) ?
O10 N4 C31 C32 . . . . -113.3(12) ?
O10 N4 C31 C35 . . . . 68.5(13) ?
O9A N4 C31 C32 . . . . 120.0(14) ?
O9A N4 C31 C35 . . . . -58.2(15) ?
O10A N4 C31 C32 . . . . -63.1(16) ?
O10A N4 C31 C35 . . . . 118.7(16) ?

_cod_database_fobs_code 2244115
