#------------------------------------------------------------------------------
#$Date: 2022-02-15 04:58:46 +0200 (Tue, 15 Feb 2022) $
#$Revision: 272960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/25/2022545.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_2022545
loop_
_publ_author_name
'Smith, Gary L. N.'
'Taylor, Richard W.'
_publ_section_title
;
 Synthesis and structures of three benzoannelated macrobicyclic diamides
;
_journal_coeditor_code           JX3069
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622001449
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C24 H28 N2 O7'
_chemical_formula_moiety         'C24 H28 N2 O7'
_chemical_formula_sum            'C24 H28 N2 O7'
_chemical_formula_weight         456.48
_chemical_name_common
6,7,9,10,12,13,20,21-Octahydro-5,14-(ethanooxyethano)dibenzo[e,q]-[1,4,10,13,7,16]tetraoxadiazacyclooctadecine-23,27-dione
_chemical_name_systematic
8,11,21,24,29-pentaoxa-1,18-diazatetracyclo[16.8.5.0^2,7^.0^12,17^]hentriaconta-2,4,6,12,14,16-hexaene-27,31-dione
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.6770(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6238(7)
_cell_length_b                   23.318(2)
_cell_length_c                   12.6550(12)
_cell_measurement_reflns_used    7345
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      3.2
_cell_volume                     2210.8(3)
_computing_cell_refinement
;
SMART (Bruker, 1998)
;
_computing_data_collection
;
SMART (Bruker, 1998)
;
_computing_data_reduction
;
SAINT (Bruker, 1998)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26492
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.527
_diffrn_reflns_theta_min         1.637
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details
;
Flack x determined using 4079 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         10031
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0370
_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)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0891
_reflns_number_gt                9276
_reflns_number_total             10031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jx3069sup1.cif
_cod_data_source_block           rt4048a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022545
_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   0.970
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O O1 1.0467(2) 0.70914(7) 0.56596(13) 0.0192(4) Uani d 1 . .
O O2 0.9632(2) 0.74135(7) 0.76497(13) 0.0180(3) Uani d 1 . .
O O3 0.9192(2) 0.93097(7) 0.59815(15) 0.0239(4) Uani d 1 . .
O O4 1.0924(2) 0.84220(7) 0.46310(14) 0.0214(4) Uani d 1 . .
O O5 0.6319(2) 0.81555(8) 0.40074(15) 0.0238(4) Uani d 1 . .
O O6 0.4588(2) 0.74674(8) 0.52483(14) 0.0218(4) Uani d 1 . .
O O7 0.5620(2) 0.74078(8) 0.74883(14) 0.0216(4) Uani d 1 . .
N N1 0.8343(3) 0.74777(9) 0.37970(15) 0.0176(4) Uani d 1 . .
N N2 0.7034(3) 0.82564(9) 0.74816(16) 0.0175(4) Uani d 1 . .
C C1 0.9021(3) 0.68998(10) 0.3891(2) 0.0187(5) Uani d 1 . .
C C2 0.8633(3) 0.65364(11) 0.3012(2) 0.0217(5) Uani d 1 . .
H H2A 0.782488 0.665803 0.238892 0.026 Uiso calc 1 . .
C C3 0.9410(4) 0.59959(11) 0.3030(2) 0.0245(5) Uani d 1 . .
H H3A 0.912322 0.574761 0.242799 0.029 Uiso calc 1 . .
C C4 1.0609(4) 0.58229(11) 0.3939(2) 0.0236(5) Uani d 1 . .
H H4A 1.117116 0.545890 0.394802 0.028 Uiso calc 1 . .
C C5 1.0992(3) 0.61762(11) 0.4830(2) 0.0208(5) Uani d 1 . .
H H5A 1.179995 0.605033 0.545072 0.025 Uiso calc 1 . .
C C6 1.0196(3) 0.67192(10) 0.48248(19) 0.0182(5) Uani d 1 . .
C C7 1.1487(3) 0.68882(11) 0.66645(19) 0.0183(5) Uani d 1 . .
H H7A 1.273338 0.681043 0.658624 0.022 Uiso calc 1 . .
H H7B 1.096366 0.652800 0.688043 0.022 Uiso calc 1 . .
C C8 1.1452(3) 0.73402(10) 0.74978(19) 0.0181(5) Uani d 1 . .
H H8A 1.221931 0.722443 0.818362 0.022 Uiso calc 1 . .
H H8B 1.191315 0.770627 0.726174 0.022 Uiso calc 1 . .
C C9 0.9440(3) 0.76965(10) 0.85723(19) 0.0166(5) Uani d 1 . .
C C10 1.0456(3) 0.75635(10) 0.95758(19) 0.0176(5) Uani d 1 . .
H H10A 1.133433 0.727019 0.963895 0.021 Uiso calc 1 . .
C C11 1.0184(3) 0.78598(10) 1.04812(19) 0.0184(5) Uani d 1 . .
H H11A 1.088237 0.776752 1.116203 0.022 Uiso calc 1 . .
C C12 0.8900(3) 0.82912(11) 1.0409(2) 0.0195(5) Uani d 1 . .
H H12A 0.873072 0.849539 1.103158 0.023 Uiso calc 1 . .
C C13 0.7877(3) 0.84169(10) 0.9415(2) 0.0182(5) Uani d 1 . .
H H13A 0.699614 0.870911 0.935585 0.022 Uiso calc 1 . .
C C14 0.8124(3) 0.81205(10) 0.85032(19) 0.0170(5) Uani d 1 . .
C C15 0.7397(3) 0.88083(10) 0.7001(2) 0.0201(5) Uani d 1 . .
H H15A 0.768032 0.910119 0.757369 0.024 Uiso calc 1 . .
H H15B 0.631933 0.893570 0.649390 0.024 Uiso calc 1 . .
C C16 0.8948(3) 0.87558(11) 0.6409(2) 0.0203(5) Uani d 1 . .
H H16A 1.004103 0.863344 0.690792 0.024 Uiso calc 1 . .
H H16B 0.867407 0.847024 0.582270 0.024 Uiso calc 1 . .
C C17 1.0638(4) 0.93428(11) 0.5412(2) 0.0260(6) Uani d 1 . .
H H17A 1.173704 0.920747 0.589022 0.031 Uiso calc 1 . .
H H17B 1.082357 0.974981 0.523851 0.031 Uiso calc 1 . .
C C18 1.0380(4) 0.89996(11) 0.4383(2) 0.0253(6) Uani d 1 . .
H H18A 0.910940 0.900871 0.402820 0.030 Uiso calc 1 . .
H H18B 1.110051 0.916745 0.388528 0.030 Uiso calc 1 . .
C C19 1.1014(3) 0.80726(11) 0.3724(2) 0.0211(5) Uani d 1 . .
H H19A 1.176759 0.773412 0.396269 0.025 Uiso calc 1 . .
H H19B 1.159982 0.829208 0.321652 0.025 Uiso calc 1 . .
C C20 0.9198(3) 0.78676(11) 0.31341(19) 0.0204(5) Uani d 1 . .
H H20A 0.841539 0.820354 0.292911 0.025 Uiso calc 1 . .
H H20B 0.934674 0.766766 0.246608 0.025 Uiso calc 1 . .
C C21 0.6945(3) 0.76770(11) 0.42196(19) 0.0187(5) Uani d 1 . .
C C22 0.6222(3) 0.72766(11) 0.4992(2) 0.0211(5) Uani d 1 . .
H H22A 0.604566 0.689051 0.466394 0.025 Uiso calc 1 . .
H H22B 0.711816 0.724250 0.566326 0.025 Uiso calc 1 . .
C C23 0.4767(3) 0.79713(11) 0.5898(2) 0.0221(5) Uani d 1 . .
H H23A 0.356802 0.811382 0.596194 0.027 Uiso calc 1 . .
H H23B 0.537017 0.827396 0.554890 0.027 Uiso calc 1 . .
C C24 0.5844(3) 0.78504(10) 0.70187(19) 0.0183(5) Uani d 1 . .
O O8 0.3760(2) 1.06054(7) 0.21512(13) 0.0189(4) Uani d 1 . .
O O9 0.4849(2) 1.13290(7) 0.06159(14) 0.0209(4) Uani d 1 . .
O O10 0.4675(3) 0.95660(8) -0.14362(15) 0.0265(4) Uani d 1 . .
O O11 0.2807(2) 0.94715(7) 0.05527(14) 0.0223(4) Uani d 1 . .
O O12 0.7357(3) 0.92828(8) 0.15803(17) 0.0287(4) Uani d 1 . .
O O13 0.9491(2) 1.02252(8) 0.19929(14) 0.0209(4) Uani d 1 . .
O O14 0.8659(2) 1.12678(7) 0.10206(14) 0.0204(4) Uani d 1 . .
N N3 0.5443(3) 0.95659(9) 0.26409(16) 0.0181(4) Uani d 1 . .
N N4 0.7236(3) 1.08640(9) -0.05243(17) 0.0192(4) Uani d 1 . .
C C25 0.4977(3) 0.99303(10) 0.3464(2) 0.0186(5) Uani d 1 . .
C C26 0.5354(3) 0.97450(11) 0.4525(2) 0.0224(5) Uani d 1 . .
H H26A 0.597774 0.939473 0.469690 0.027 Uiso calc 1 . .
C C27 0.4831(4) 1.00646(12) 0.5338(2) 0.0255(5) Uani d 1 . .
H H27A 0.511070 0.993857 0.606332 0.031 Uiso calc 1 . .
C C28 0.3896(4) 1.05694(12) 0.5078(2) 0.0247(5) Uani d 1 . .
H H28A 0.351204 1.078561 0.562941 0.030 Uiso calc 1 . .
C C29 0.3510(3) 1.07648(11) 0.4025(2) 0.0228(5) Uani d 1 . .
H H29A 0.287822 1.111433 0.386165 0.027 Uiso calc 1 . .
C C30 0.4051(3) 1.04481(10) 0.32035(19) 0.0175(5) Uani d 1 . .
C C31 0.2994(3) 1.11669(10) 0.1914(2) 0.0193(5) Uani d 1 . .
H H31A 0.369600 1.145735 0.238356 0.023 Uiso calc 1 . .
H H31B 0.175319 1.117393 0.204444 0.023 Uiso calc 1 . .
C C32 0.3016(3) 1.12985(11) 0.0758(2) 0.0219(5) Uani d 1 . .
H H32A 0.237731 1.099475 0.029231 0.026 Uiso calc 1 . .
H H32B 0.240915 1.166855 0.055600 0.026 Uiso calc 1 . .
C C33 0.5171(3) 1.16340(10) -0.02533(19) 0.0185(5) Uani d 1 . .
C C34 0.4433(3) 1.21743(11) -0.0529(2) 0.0222(5) Uani d 1 . .
H H34A 0.366653 1.234651 -0.010776 0.027 Uiso calc 1 . .
C C35 0.4826(3) 1.24583(12) -0.1420(2) 0.0259(6) Uani d 1 . .
H H35A 0.432266 1.282568 -0.160519 0.031 Uiso calc 1 . .
C C36 0.5941(3) 1.22141(12) -0.2045(2) 0.0262(6) Uani d 1 . .
H H36A 0.615862 1.240465 -0.267219 0.031 Uiso calc 1 . .
C C37 0.6736(3) 1.16899(12) -0.1748(2) 0.0236(5) Uani d 1 . .
H H37A 0.753687 1.152719 -0.215765 0.028 Uiso calc 1 . .
C C38 0.6368(3) 1.13998(10) -0.08521(19) 0.0182(5) Uani d 1 . .
C C39 0.6639(4) 1.03563(11) -0.1184(2) 0.0223(5) Uani d 1 . .
H H39A 0.761438 1.007022 -0.109747 0.027 Uiso calc 1 . .
H H39B 0.635489 1.046841 -0.195105 0.027 Uiso calc 1 . .
C C40 0.5003(4) 1.00895(11) -0.0859(2) 0.0229(5) Uani d 1 . .
H H40A 0.522073 1.001650 -0.007527 0.027 Uiso calc 1 . .
H H40B 0.396356 1.034923 -0.104292 0.027 Uiso calc 1 . .
C C41 0.3080(4) 0.92802(13) -0.1284(2) 0.0300(6) Uani d 1 . .
H H41A 0.282705 0.896541 -0.181514 0.036 Uiso calc 1 . .
H H41B 0.207578 0.955536 -0.143793 0.036 Uiso calc 1 . .
C C42 0.3134(4) 0.90330(12) -0.0173(2) 0.0284(6) Uani d 1 . .
H H42A 0.221895 0.872890 -0.020673 0.034 Uiso calc 1 . .
H H42B 0.431778 0.885846 0.008997 0.034 Uiso calc 1 . .
C C43 0.2544(3) 0.92539(11) 0.1568(2) 0.0210(5) Uani d 1 . .
H H43A 0.173565 0.891848 0.144181 0.025 Uiso calc 1 . .
H H43B 0.194590 0.955192 0.193181 0.025 Uiso calc 1 . .
C C44 0.4261(3) 0.90754(10) 0.2311(2) 0.0205(5) Uani d 1 . .
H H44A 0.396363 0.888932 0.295889 0.025 Uiso calc 1 . .
H H44B 0.489468 0.879098 0.193874 0.025 Uiso calc 1 . .
C C45 0.6901(3) 0.96398(10) 0.2189(2) 0.0196(5) Uani d 1 . .
C C46 0.7941(3) 1.01977(11) 0.2457(2) 0.0208(5) Uani d 1 . .
H H46A 0.715554 1.052581 0.219542 0.025 Uiso calc 1 . .
H H46B 0.829077 1.023321 0.324746 0.025 Uiso calc 1 . .
C C47 0.9109(3) 1.02589(11) 0.0848(2) 0.0213(5) Uani d 1 . .
H H47A 0.826187 0.995060 0.055897 0.026 Uiso calc 1 . .
H H47B 1.022286 1.019883 0.056566 0.026 Uiso calc 1 . .
C C48 0.8305(3) 1.08407(10) 0.0466(2) 0.0185(5) 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
C6 O1 C7 . . 117.21(19) ?
C9 O2 C8 . . 115.21(18) ?
C16 O3 C17 . . 114.11(19) ?
C19 O4 C18 . . 114.81(19) ?
C22 O6 C23 . . 113.39(19) ?
C21 N1 C1 . . 125.7(2) ?
C21 N1 C20 . . 118.5(2) ?
C1 N1 C20 . . 115.8(2) ?
C24 N2 C14 . . 117.4(2) ?
C24 N2 C15 . . 126.2(2) ?
C14 N2 C15 . . 116.3(2) ?
C2 C1 C6 . . 119.9(2) ?
C2 C1 N1 . . 119.1(2) ?
C6 C1 N1 . . 120.7(2) ?
C1 C2 C3 . . 120.9(2) ?
C1 C2 H2A . . 119.5 ?
C3 C2 H2A . . 119.5 ?
C4 C3 C2 . . 119.3(2) ?
C4 C3 H3A . . 120.3 ?
C2 C3 H3A . . 120.3 ?
C5 C4 C3 . . 120.6(2) ?
C5 C4 H4A . . 119.7 ?
C3 C4 H4A . . 119.7 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5A . . 119.8 ?
C6 C5 H5A . . 119.8 ?
O1 C6 C5 . . 124.8(2) ?
O1 C6 C1 . . 116.4(2) ?
C5 C6 C1 . . 118.7(2) ?
O1 C7 C8 . . 108.26(19) ?
O1 C7 H7A . . 110.0 ?
C8 C7 H7A . . 110.0 ?
O1 C7 H7B . . 110.0 ?
C8 C7 H7B . . 110.0 ?
H7A C7 H7B . . 108.4 ?
O2 C8 C7 . . 108.67(19) ?
O2 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
O2 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.3 ?
O2 C9 C10 . . 122.6(2) ?
O2 C9 C14 . . 118.3(2) ?
C10 C9 C14 . . 119.0(2) ?
C11 C10 C9 . . 119.9(2) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C10 C11 C12 . . 121.1(2) ?
C10 C11 H11A . . 119.5 ?
C12 C11 H11A . . 119.5 ?
C13 C12 C11 . . 118.9(2) ?
C13 C12 H12A . . 120.5 ?
C11 C12 H12A . . 120.5 ?
C12 C13 C14 . . 120.7(2) ?
C12 C13 H13A . . 119.7 ?
C14 C13 H13A . . 119.7 ?
C13 C14 C9 . . 120.4(2) ?
C13 C14 N2 . . 119.5(2) ?
C9 C14 N2 . . 120.0(2) ?
N2 C15 C16 . . 110.9(2) ?
N2 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
N2 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.0 ?
O3 C16 C15 . . 106.44(19) ?
O3 C16 H16A . . 110.4 ?
C15 C16 H16A . . 110.4 ?
O3 C16 H16B . . 110.4 ?
C15 C16 H16B . . 110.4 ?
H16A C16 H16B . . 108.6 ?
O3 C17 C18 . . 114.7(2) ?
O3 C17 H17A . . 108.6 ?
C18 C17 H17A . . 108.6 ?
O3 C17 H17B . . 108.6 ?
C18 C17 H17B . . 108.6 ?
H17A C17 H17B . . 107.6 ?
O4 C18 C17 . . 109.0(2) ?
O4 C18 H18A . . 109.9 ?
C17 C18 H18A . . 109.9 ?
O4 C18 H18B . . 109.9 ?
C17 C18 H18B . . 109.9 ?
H18A C18 H18B . . 108.3 ?
O4 C19 C20 . . 113.6(2) ?
O4 C19 H19A . . 108.8 ?
C20 C19 H19A . . 108.8 ?
O4 C19 H19B . . 108.8 ?
C20 C19 H19B . . 108.8 ?
H19A C19 H19B . . 107.7 ?
N1 C20 C19 . . 112.0(2) ?
N1 C20 H20A . . 109.2 ?
C19 C20 H20A . . 109.2 ?
N1 C20 H20B . . 109.2 ?
C19 C20 H20B . . 109.2 ?
H20A C20 H20B . . 107.9 ?
O5 C21 N1 . . 121.8(2) ?
O5 C21 C22 . . 121.7(2) ?
N1 C21 C22 . . 116.4(2) ?
O6 C22 C21 . . 113.1(2) ?
O6 C22 H22A . . 109.0 ?
C21 C22 H22A . . 109.0 ?
O6 C22 H22B . . 109.0 ?
C21 C22 H22B . . 109.0 ?
H22A C22 H22B . . 107.8 ?
O6 C23 C24 . . 111.2(2) ?
O6 C23 H23A . . 109.4 ?
C24 C23 H23A . . 109.4 ?
O6 C23 H23B . . 109.4 ?
C24 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
O7 C24 N2 . . 121.3(2) ?
O7 C24 C23 . . 120.6(2) ?
N2 C24 C23 . . 118.0(2) ?
C30 O8 C31 . . 115.77(18) ?
C33 O9 C32 . . 116.60(18) ?
C40 O10 C41 . . 113.8(2) ?
C42 O11 C43 . . 113.24(19) ?
C46 O13 C47 . . 113.28(19) ?
C45 N3 C25 . . 124.3(2) ?
C45 N3 C44 . . 119.3(2) ?
C25 N3 C44 . . 116.39(19) ?
C48 N4 C38 . . 117.7(2) ?
C48 N4 C39 . . 124.0(2) ?
C38 N4 C39 . . 117.24(19) ?
C26 C25 C30 . . 119.9(2) ?
C26 C25 N3 . . 118.8(2) ?
C30 C25 N3 . . 121.2(2) ?
C27 C26 C25 . . 120.9(2) ?
C27 C26 H26A . . 119.6 ?
C25 C26 H26A . . 119.6 ?
C28 C27 C26 . . 119.2(2) ?
C28 C27 H27A . . 120.4 ?
C26 C27 H27A . . 120.4 ?
C27 C28 C29 . . 121.0(2) ?
C27 C28 H28A . . 119.5 ?
C29 C28 H28A . . 119.5 ?
C28 C29 C30 . . 120.1(2) ?
C28 C29 H29A . . 119.9 ?
C30 C29 H29A . . 119.9 ?
O8 C30 C29 . . 124.7(2) ?
O8 C30 C25 . . 116.4(2) ?
C29 C30 C25 . . 118.9(2) ?
O8 C31 C32 . . 108.16(19) ?
O8 C31 H31A . . 110.1 ?
C32 C31 H31A . . 110.1 ?
O8 C31 H31B . . 110.1 ?
C32 C31 H31B . . 110.1 ?
H31A C31 H31B . . 108.4 ?
O9 C32 C31 . . 108.6(2) ?
O9 C32 H32A . . 110.0 ?
C31 C32 H32A . . 110.0 ?
O9 C32 H32B . . 110.0 ?
C31 C32 H32B . . 110.0 ?
H32A C32 H32B . . 108.4 ?
O9 C33 C34 . . 123.0(2) ?
O9 C33 C38 . . 117.6(2) ?
C34 C33 C38 . . 119.3(2) ?
C35 C34 C33 . . 119.7(3) ?
C35 C34 H34A . . 120.1 ?
C33 C34 H34A . . 120.1 ?
C36 C35 C34 . . 121.0(2) ?
C36 C35 H35A . . 119.5 ?
C34 C35 H35A . . 119.5 ?
C37 C36 C35 . . 119.4(2) ?
C37 C36 H36A . . 120.3 ?
C35 C36 H36A . . 120.3 ?
C36 C37 C38 . . 120.4(3) ?
C36 C37 H37A . . 119.8 ?
C38 C37 H37A . . 119.8 ?
C37 C38 C33 . . 120.1(2) ?
C37 C38 N4 . . 120.3(2) ?
C33 C38 N4 . . 119.6(2) ?
N4 C39 C40 . . 111.1(2) ?
N4 C39 H39A . . 109.4 ?
C40 C39 H39A . . 109.4 ?
N4 C39 H39B . . 109.4 ?
C40 C39 H39B . . 109.4 ?
H39A C39 H39B . . 108.0 ?
O10 C40 C39 . . 106.8(2) ?
O10 C40 H40A . . 110.4 ?
C39 C40 H40A . . 110.4 ?
O10 C40 H40B . . 110.4 ?
C39 C40 H40B . . 110.4 ?
H40A C40 H40B . . 108.6 ?
O10 C41 C42 . . 115.2(2) ?
O10 C41 H41A . . 108.5 ?
C42 C41 H41A . . 108.5 ?
O10 C41 H41B . . 108.5 ?
C42 C41 H41B . . 108.5 ?
H41A C41 H41B . . 107.5 ?
O11 C42 C41 . . 110.3(2) ?
O11 C42 H42A . . 109.6 ?
C41 C42 H42A . . 109.6 ?
O11 C42 H42B . . 109.6 ?
C41 C42 H42B . . 109.6 ?
H42A C42 H42B . . 108.1 ?
O11 C43 C44 . . 113.9(2) ?
O11 C43 H43A . . 108.8 ?
C44 C43 H43A . . 108.8 ?
O11 C43 H43B . . 108.8 ?
C44 C43 H43B . . 108.8 ?
H43A C43 H43B . . 107.7 ?
N3 C44 C43 . . 112.0(2) ?
N3 C44 H44A . . 109.2 ?
C43 C44 H44A . . 109.2 ?
N3 C44 H44B . . 109.2 ?
C43 C44 H44B . . 109.2 ?
H44A C44 H44B . . 107.9 ?
O12 C45 N3 . . 122.0(2) ?
O12 C45 C46 . . 121.4(2) ?
N3 C45 C46 . . 116.6(2) ?
O13 C46 C45 . . 112.7(2) ?
O13 C46 H46A . . 109.1 ?
C45 C46 H46A . . 109.1 ?
O13 C46 H46B . . 109.1 ?
C45 C46 H46B . . 109.1 ?
H46A C46 H46B . . 107.8 ?
O13 C47 C48 . . 111.4(2) ?
O13 C47 H47A . . 109.4 ?
C48 C47 H47A . . 109.4 ?
O13 C47 H47B . . 109.4 ?
C48 C47 H47B . . 109.4 ?
H47A C47 H47B . . 108.0 ?
O14 C48 N4 . . 121.8(2) ?
O14 C48 C47 . . 120.6(2) ?
N4 C48 C47 . . 117.5(2) ?
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 C6 . 1.353(3) ?
O1 C7 . 1.442(3) ?
O2 C9 . 1.372(3) ?
O2 C8 . 1.446(3) ?
O3 C16 . 1.426(3) ?
O3 C17 . 1.427(3) ?
O4 C19 . 1.420(3) ?
O4 C18 . 1.427(3) ?
O5 C21 . 1.224(3) ?
O6 C22 . 1.416(3) ?
O6 C23 . 1.426(3) ?
O7 C24 . 1.219(3) ?
N1 C21 . 1.360(3) ?
N1 C1 . 1.440(3) ?
N1 C20 . 1.469(3) ?
N2 C24 . 1.366(3) ?
N2 C14 . 1.437(3) ?
N2 C15 . 1.472(3) ?
C1 C2 . 1.385(3) ?
C1 C6 . 1.409(3) ?
C2 C3 . 1.391(4) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.390(4) ?
C3 H3A . 0.9500 ?
C4 C5 . 1.384(4) ?
C4 H4A . 0.9500 ?
C5 C6 . 1.404(3) ?
C5 H5A . 0.9500 ?
C7 C8 . 1.495(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.394(3) ?
C9 C14 . 1.400(3) ?
C10 C11 . 1.386(3) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.395(3) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.383(4) ?
C12 H12A . 0.9500 ?
C13 C14 . 1.387(3) ?
C13 H13A . 0.9500 ?
C15 C16 . 1.517(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 C18 . 1.509(4) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C19 C20 . 1.523(4) ?
C19 H19A . 0.9900 ?
C19 H19B . 0.9900 ?
C20 H20A . 0.9900 ?
C20 H20B . 0.9900 ?
C21 C22 . 1.526(3) ?
C22 H22A . 0.9900 ?
C22 H22B . 0.9900 ?
C23 C24 . 1.527(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
O8 C30 . 1.359(3) ?
O8 C31 . 1.442(3) ?
O9 C33 . 1.370(3) ?
O9 C32 . 1.443(3) ?
O10 C40 . 1.421(3) ?
O10 C41 . 1.431(3) ?
O11 C42 . 1.427(3) ?
O11 C43 . 1.430(3) ?
O12 C45 . 1.227(3) ?
O13 C46 . 1.415(3) ?
O13 C47 . 1.426(3) ?
O14 C48 . 1.220(3) ?
N3 C45 . 1.352(3) ?
N3 C25 . 1.439(3) ?
N3 C44 . 1.468(3) ?
N4 C48 . 1.363(3) ?
N4 C38 . 1.438(3) ?
N4 C39 . 1.471(3) ?
C25 C26 . 1.389(4) ?
C25 C30 . 1.407(3) ?
C26 C27 . 1.387(4) ?
C26 H26A . 0.9500 ?
C27 C28 . 1.384(4) ?
C27 H27A . 0.9500 ?
C28 C29 . 1.387(4) ?
C28 H28A . 0.9500 ?
C29 C30 . 1.398(3) ?
C29 H29A . 0.9500 ?
C31 C32 . 1.498(3) ?
C31 H31A . 0.9900 ?
C31 H31B . 0.9900 ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C33 C34 . 1.397(3) ?
C33 C38 . 1.400(3) ?
C34 C35 . 1.388(4) ?
C34 H34A . 0.9500 ?
C35 C36 . 1.387(4) ?
C35 H35A . 0.9500 ?
C36 C37 . 1.385(4) ?
C36 H36A . 0.9500 ?
C37 C38 . 1.393(3) ?
C37 H37A . 0.9500 ?
C39 C40 . 1.517(4) ?
C39 H39A . 0.9900 ?
C39 H39B . 0.9900 ?
C40 H40A . 0.9900 ?
C40 H40B . 0.9900 ?
C41 C42 . 1.513(4) ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C43 C44 . 1.522(4) ?
C43 H43A . 0.9900 ?
C43 H43B . 0.9900 ?
C44 H44A . 0.9900 ?
C44 H44B . 0.9900 ?
C45 C46 . 1.529(3) ?
C46 H46A . 0.9900 ?
C46 H46B . 0.9900 ?
C47 C48 . 1.530(3) ?
C47 H47A . 0.9900 ?
C47 H47B . 0.9900 ?
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
C8 H8A O14 2_746 0.99 2.59 3.136(3) 115.0 yes
C10 H10A O14 2_746 0.95 2.48 3.216(3) 134.0 yes
C16 H16B O4 . 0.99 2.49 3.033(3) 114.3 yes
C19 H19A O6 1_655 0.99 2.52 3.345(3) 140.4 yes
C22 H22B O1 . 0.99 2.58 3.219(3) 122.4 yes
C23 H23A O4 1_455 0.99 2.48 3.243(3) 133.5 yes
C23 H23B O5 . 0.99 2.22 2.891(3) 123.9 yes
C31 H31A O7 2_656 0.99 2.28 3.125(3) 143.2 yes
C31 H31B O14 1_455 0.99 2.48 3.297(3) 139.4 yes
C40 H40A O11 . 0.99 2.49 3.030(3) 114.3 yes
C43 H43B O13 1_455 0.99 2.45 3.361(3) 152.0 yes
C44 H44A O5 . 0.99 2.65 3.228(3) 117.4 yes
C46 H46A O8 . 0.99 2.59 3.280(3) 127.2 yes
C47 H47A O12 . 0.99 2.21 2.878(3) 123.2 yes
C47 H47B O11 1_655 0.99 2.60 3.442(3) 142.7 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
C21 N1 C1 C2 . . . . 104.2(3) ?
C20 N1 C1 C2 . . . . -72.3(3) ?
C21 N1 C1 C6 . . . . -81.5(3) ?
C20 N1 C1 C6 . . . . 102.0(3) ?
C6 C1 C2 C3 . . . . -1.0(4) ?
N1 C1 C2 C3 . . . . 173.3(2) ?
C1 C2 C3 C4 . . . . -0.9(4) ?
C2 C3 C4 C5 . . . . 1.9(4) ?
C3 C4 C5 C6 . . . . -1.0(4) ?
C7 O1 C6 C5 . . . . -7.4(3) ?
C7 O1 C6 C1 . . . . 172.6(2) ?
C4 C5 C6 O1 . . . . 179.1(2) ?
C4 C5 C6 C1 . . . . -0.9(3) ?
C2 C1 C6 O1 . . . . -178.1(2) ?
N1 C1 C6 O1 . . . . 7.7(3) ?
C2 C1 C6 C5 . . . . 1.9(3) ?
N1 C1 C6 C5 . . . . -172.4(2) ?
C6 O1 C7 C8 . . . . -173.84(19) ?
C9 O2 C8 C7 . . . . 163.45(19) ?
O1 C7 C8 O2 . . . . 63.9(2) ?
C8 O2 C9 C10 . . . . -47.0(3) ?
C8 O2 C9 C14 . . . . 135.4(2) ?
O2 C9 C10 C11 . . . . -179.1(2) ?
C14 C9 C10 C11 . . . . -1.6(3) ?
C9 C10 C11 C12 . . . . 0.1(4) ?
C10 C11 C12 C13 . . . . 0.7(4) ?
C11 C12 C13 C14 . . . . -0.2(4) ?
C12 C13 C14 C9 . . . . -1.3(4) ?
C12 C13 C14 N2 . . . . 179.5(2) ?
O2 C9 C14 C13 . . . . 179.8(2) ?
C10 C9 C14 C13 . . . . 2.1(3) ?
O2 C9 C14 N2 . . . . -1.0(3) ?
C10 C9 C14 N2 . . . . -178.6(2) ?
C24 N2 C14 C13 . . . . -112.3(2) ?
C15 N2 C14 C13 . . . . 71.7(3) ?
C24 N2 C14 C9 . . . . 68.5(3) ?
C15 N2 C14 C9 . . . . -107.6(2) ?
C24 N2 C15 C16 . . . . -92.9(3) ?
C14 N2 C15 C16 . . . . 82.8(3) ?
C17 O3 C16 C15 . . . . 178.7(2) ?
N2 C15 C16 O3 . . . . -179.8(2) ?
C16 O3 C17 C18 . . . . 66.6(3) ?
C19 O4 C18 C17 . . . . -170.7(2) ?
O3 C17 C18 O4 . . . . -84.8(3) ?
C18 O4 C19 C20 . . . . -77.5(3) ?
C21 N1 C20 C19 . . . . 106.3(2) ?
C1 N1 C20 C19 . . . . -76.9(3) ?
O4 C19 C20 N1 . . . . -65.7(3) ?
C1 N1 C21 O5 . . . . -171.7(2) ?
C20 N1 C21 O5 . . . . 4.7(3) ?
C1 N1 C21 C22 . . . . 9.5(3) ?
C20 N1 C21 C22 . . . . -174.1(2) ?
C23 O6 C22 C21 . . . . -69.4(3) ?
O5 C21 C22 O6 . . . . 11.7(3) ?
N1 C21 C22 O6 . . . . -169.5(2) ?
C22 O6 C23 C24 . . . . -67.1(3) ?
C14 N2 C24 O7 . . . . 5.4(3) ?
C15 N2 C24 O7 . . . . -179.1(2) ?
C14 N2 C24 C23 . . . . -175.8(2) ?
C15 N2 C24 C23 . . . . -0.3(3) ?
O6 C23 C24 O7 . . . . -40.8(3) ?
O6 C23 C24 N2 . . . . 140.3(2) ?
C45 N3 C25 C26 . . . . -101.0(3) ?
C44 N3 C25 C26 . . . . 77.1(3) ?
C45 N3 C25 C30 . . . . 83.2(3) ?
C44 N3 C25 C30 . . . . -98.8(3) ?
C30 C25 C26 C27 . . . . -0.1(4) ?
N3 C25 C26 C27 . . . . -176.0(2) ?
C25 C26 C27 C28 . . . . 1.1(4) ?
C26 C27 C28 C29 . . . . -1.4(4) ?
C27 C28 C29 C30 . . . . 0.7(4) ?
C31 O8 C30 C29 . . . . 6.3(3) ?
C31 O8 C30 C25 . . . . -173.2(2) ?
C28 C29 C30 O8 . . . . -179.1(2) ?
C28 C29 C30 C25 . . . . 0.3(4) ?
C26 C25 C30 O8 . . . . 178.9(2) ?
N3 C25 C30 O8 . . . . -5.3(3) ?
C26 C25 C30 C29 . . . . -0.6(3) ?
N3 C25 C30 C29 . . . . 175.2(2) ?
C30 O8 C31 C32 . . . . 172.0(2) ?
C33 O9 C32 C31 . . . . -157.7(2) ?
O8 C31 C32 O9 . . . . -64.2(2) ?
C32 O9 C33 C34 . . . . 45.8(3) ?
C32 O9 C33 C38 . . . . -137.4(2) ?
O9 C33 C34 C35 . . . . 179.8(2) ?
C38 C33 C34 C35 . . . . 3.1(4) ?
C33 C34 C35 C36 . . . . 0.0(4) ?
C34 C35 C36 C37 . . . . -2.8(4) ?
C35 C36 C37 C38 . . . . 2.4(4) ?
C36 C37 C38 C33 . . . . 0.8(4) ?
C36 C37 C38 N4 . . . . -178.1(2) ?
O9 C33 C38 C37 . . . . 179.6(2) ?
C34 C33 C38 C37 . . . . -3.6(4) ?
O9 C33 C38 N4 . . . . -1.5(3) ?
C34 C33 C38 N4 . . . . 175.3(2) ?
C48 N4 C38 C37 . . . . 117.8(3) ?
C39 N4 C38 C37 . . . . -73.8(3) ?
C48 N4 C38 C33 . . . . -61.1(3) ?
C39 N4 C38 C33 . . . . 107.3(3) ?
C48 N4 C39 C40 . . . . 83.7(3) ?
C38 N4 C39 C40 . . . . -83.9(3) ?
C41 O10 C40 C39 . . . . -175.3(2) ?
N4 C39 C40 O10 . . . . -172.5(2) ?
C40 O10 C41 C42 . . . . -69.2(3) ?
C43 O11 C42 C41 . . . . 170.2(2) ?
O10 C41 C42 O11 . . . . 80.5(3) ?
C42 O11 C43 C44 . . . . 76.9(3) ?
C45 N3 C44 C43 . . . . -104.4(3) ?
C25 N3 C44 C43 . . . . 77.4(3) ?
O11 C43 C44 N3 . . . . 65.3(3) ?
C25 N3 C45 O12 . . . . 171.5(2) ?
C44 N3 C45 O12 . . . . -6.5(4) ?
C25 N3 C45 C46 . . . . -9.6(3) ?
C44 N3 C45 C46 . . . . 172.4(2) ?
C47 O13 C46 C45 . . . . 67.1(3) ?
O12 C45 C46 O13 . . . . -4.1(3) ?
N3 C45 C46 O13 . . . . 177.0(2) ?
C46 O13 C47 C48 . . . . 70.2(3) ?
C38 N4 C48 O14 . . . . -6.7(3) ?
C39 N4 C48 O14 . . . . -174.3(2) ?
C38 N4 C48 C47 . . . . 175.3(2) ?
C39 N4 C48 C47 . . . . 7.7(3) ?
O13 C47 C48 O14 . . . . 28.0(3) ?
O13 C47 C48 N4 . . . . -154.0(2) ?

_cod_database_fobs_code 2022545
