#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/71/4507185.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_4507185
loop_
_publ_author_name
'Białońska, Agata'
'Ciunik, Zbigniew'
_publ_section_title
;
 Why Is the Resolution of Certain Racemic Modifications Inefficient?
 Formation of Diastereomeric Double Salts of Brucinium
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              111
_journal_paper_doi               10.1021/cg3012469
_journal_volume                  13
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety
;
C23 H27 N2 O4, C10 H8 N3 O8, 2.5(C H4 O)
;
_chemical_formula_sum            'C35.5 H45 N5 O14.5'
_chemical_formula_weight         773.77
_chemical_melting_point          416
_chemical_name_systematic
; 
brucinium N-(3,5-dinitrobenzoyl)-D-serinate methanol 2.5-solvate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.397(4)
_cell_length_b                   14.143(3)
_cell_length_c                   8.675(2)
_cell_measurement_reflns_used    12194
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.67
_cell_measurement_theta_min      2.87
_cell_volume                     3594.7(13)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kuma KM4CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15466
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1636
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         4083
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.9386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                3889
_reflns_number_total             4083
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3012469_si_002.cif
_cod_data_source_block           bdnbds
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '416 K' was changed to '416' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3594.7(12)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C35.50 H45 N5 O14.50'
_cod_database_code               4507185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22228(5) 0.01659(10) 1.26543(16) 0.0231(3) Uani 1 1 d . . .
O2 O 0.30754(5) 0.31589(11) 0.50676(17) 0.0249(3) Uani 1 1 d . . .
O3 O 0.22820(5) 0.39311(10) 0.41419(16) 0.0229(3) Uani 1 1 d . . .
O4 O 0.32753(5) 0.08972(12) 0.97153(17) 0.0266(3) Uani 1 1 d . . .
N1 N 0.25150(5) 0.12176(12) 0.88956(18) 0.0180(3) Uani 1 1 d . . .
N2 N 0.10092(5) 0.17901(12) 0.85652(18) 0.0184(3) Uani 1 1 d . . .
H2 H 0.0745 0.2081 0.7959 0.022 Uiso 1 1 d R . .
C1 C 0.28565(6) 0.21608(14) 0.7029(2) 0.0192(4) Uani 1 1 d . . .
H1 H 0.3149 0.1874 0.7367 0.023 Uiso 1 1 calc R . .
C2 C 0.27620(7) 0.28500(14) 0.5848(2) 0.0198(4) Uani 1 1 d . . .
C3 C 0.23285(6) 0.32725(14) 0.5336(2) 0.0195(4) Uani 1 1 d . . .
C4 C 0.19826(6) 0.30017(14) 0.6018(2) 0.0184(4) Uani 1 1 d . . .
H4 H 0.1688 0.3281 0.5679 0.022 Uiso 1 1 calc R . .
C5 C 0.20756(6) 0.23135(13) 0.7209(2) 0.0174(4) Uani 1 1 d . . .
C6 C 0.25041(6) 0.19061(13) 0.7699(2) 0.0183(4) Uani 1 1 d . . .
C7 C 0.17504(6) 0.18186(14) 0.7998(2) 0.0168(4) Uani 1 1 d . . .
C8 C 0.20804(6) 0.12439(14) 0.9357(2) 0.0164(3) Uani 1 1 d . . .
H8 H 0.1961 0.0586 0.9374 0.020 Uiso 1 1 calc R . .
C9 C 0.28945(6) 0.08585(15) 0.9946(2) 0.0204(4) Uani 1 1 d . . .
C10 C 0.27999(7) 0.03855(16) 1.1395(2) 0.0225(4) Uani 1 1 d . . .
H10A H 0.3095 0.0287 1.2203 0.027 Uiso 1 1 calc R . .
H10B H 0.2668 -0.0246 1.1068 0.027 Uiso 1 1 calc R . .
C11 C 0.24776(6) 0.09187(14) 1.2200(2) 0.0202(4) Uani 1 1 d . . .
H11 H 0.2663 0.1243 1.3183 0.024 Uiso 1 1 calc R . .
C12 C 0.19063(7) 0.04512(16) 1.3533(2) 0.0250(4) Uani 1 1 d . . .
H12A H 0.2021 0.1024 1.4169 0.030 Uiso 1 1 calc R . .
H12B H 0.1874 -0.0058 1.4279 0.030 Uiso 1 1 calc R . .
C13 C 0.14491(7) 0.06557(14) 1.2384(2) 0.0228(4) Uani 1 1 d . . .
H13 H 0.1198 0.0251 1.2362 0.027 Uiso 1 1 calc R . .
C14 C 0.13906(6) 0.13954(13) 1.1395(2) 0.0191(4) Uani 1 1 d . . .
C15 C 0.09439(6) 0.16020(15) 1.0207(2) 0.0203(4) Uani 1 1 d . . .
H15A H 0.0801 0.2161 1.0564 0.024 Uiso 1 1 calc R . .
H15B H 0.0736 0.1057 1.0150 0.024 Uiso 1 1 calc R . .
C16 C 0.10728(6) 0.08903(14) 0.7714(2) 0.0193(4) Uani 1 1 d . . .
H16A H 0.0782 0.0691 0.6959 0.023 Uiso 1 1 calc R . .
H16B H 0.1185 0.0374 0.8488 0.023 Uiso 1 1 calc R . .
C17 C 0.14249(6) 0.11439(14) 0.6826(2) 0.0187(4) Uani 1 1 d . . .
H17A H 0.1281 0.1464 0.5801 0.022 Uiso 1 1 calc R . .
H17B H 0.1588 0.0574 0.6611 0.022 Uiso 1 1 calc R . .
C18 C 0.21939(6) 0.16620(14) 1.1050(2) 0.0180(4) Uani 1 1 d . . .
H18 H 0.2406 0.2201 1.1046 0.022 Uiso 1 1 calc R . .
C19 C 0.17734(6) 0.20979(14) 1.1447(2) 0.0181(4) Uani 1 1 d . . .
H19 H 0.1870 0.2383 1.2540 0.022 Uiso 1 1 calc R . .
C20 C 0.15976(6) 0.28901(14) 1.0222(2) 0.0192(4) Uani 1 1 d . . .
H20A H 0.1353 0.3250 1.0520 0.023 Uiso 1 1 calc R . .
H20B H 0.1849 0.3332 1.0207 0.023 Uiso 1 1 calc R . .
C21 C 0.14129(6) 0.24491(13) 0.8580(2) 0.0176(4) Uani 1 1 d . . .
H21 H 0.1304 0.2965 0.7782 0.021 Uiso 1 1 calc R . .
C22 C 0.35420(7) 0.28980(18) 0.5761(3) 0.0302(5) Uani 1 1 d . . .
H22A H 0.3736 0.3203 0.5168 0.045 Uiso 1 1 calc R . .
H22B H 0.3573 0.2210 0.5709 0.045 Uiso 1 1 calc R . .
H22C H 0.3636 0.3103 0.6880 0.045 Uiso 1 1 calc R . .
C23 C 0.18680(8) 0.44672(15) 0.3734(3) 0.0265(4) Uani 1 1 d . . .
H23A H 0.1878 0.4922 0.2892 0.040 Uiso 1 1 calc R . .
H23B H 0.1835 0.4807 0.4681 0.040 Uiso 1 1 calc R . .
H23C H 0.1608 0.4040 0.3350 0.040 Uiso 1 1 calc R . .
O5 O -0.02235(5) 0.25871(10) 0.29839(15) 0.0210(3) Uani 1 1 d . . .
O6 O -0.04115(5) 0.35217(10) 0.08508(16) 0.0223(3) Uani 1 1 d . . .
O7 O 0.08638(5) 0.28814(11) 0.32204(17) 0.0265(3) Uani 1 1 d . . .
H7 H 0.0789 0.2320 0.3329 0.040 Uiso 1 1 d R . .
O8 O 0.03844(5) 0.59127(11) 0.33617(17) 0.0288(3) Uani 1 1 d . . .
O9 O 0.05043(8) 0.89618(13) 0.0975(3) 0.0537(5) Uani 1 1 d . . .
O10 O 0.06575(7) 0.90795(12) -0.1304(3) 0.0448(5) Uani 1 1 d . . .
O11 O 0.11890(6) 0.62874(14) -0.35058(19) 0.0367(4) Uani 1 1 d . . .
O12 O 0.09818(6) 0.49111(12) -0.2848(2) 0.0369(4) Uani 1 1 d . . .
N3 N 0.03535(5) 0.45852(11) 0.18659(19) 0.0194(3) Uani 1 1 d . . .
H3 H 0.0381 0.4343 0.0962 0.023 Uiso 1 1 d R . .
N4 N 0.05981(7) 0.86141(14) -0.0187(3) 0.0332(4) Uani 1 1 d . . .
N5 N 0.10060(6) 0.57751(15) -0.2720(2) 0.0279(4) Uani 1 1 d . . .
C24 C -0.01637(6) 0.33094(13) 0.2186(2) 0.0178(4) Uani 1 1 d . . .
C25 C 0.02268(6) 0.39760(14) 0.3026(2) 0.0193(4) Uani 1 1 d . . .
H25 H 0.0103 0.4397 0.3736 0.023 Uiso 1 1 calc R . .
C26 C 0.06468(7) 0.34898(15) 0.4095(2) 0.0228(4) Uani 1 1 d . . .
H26A H 0.0867 0.3977 0.4645 0.027 Uiso 1 1 calc R . .
H26B H 0.0554 0.3118 0.4924 0.027 Uiso 1 1 calc R . .
C27 C 0.04289(6) 0.55096(14) 0.2150(2) 0.0200(4) Uani 1 1 d . . .
C28 C 0.05649(6) 0.60666(14) 0.0868(2) 0.0190(4) Uani 1 1 d . . .
C29 C 0.05385(6) 0.70482(14) 0.0947(2) 0.0216(4) Uani 1 1 d . . .
H29 H 0.0451 0.7345 0.1802 0.026 Uiso 1 1 calc R . .
C30 C 0.06431(7) 0.75842(15) -0.0247(3) 0.0252(4) Uani 1 1 d . . .
C31 C 0.07877(7) 0.71957(16) -0.1491(3) 0.0252(4) Uani 1 1 d . . .
H31 H 0.0860 0.7575 -0.2294 0.030 Uiso 1 1 calc R . .
C32 C 0.08202(6) 0.62223(16) -0.1493(2) 0.0223(4) Uani 1 1 d . . .
C33 C 0.07078(6) 0.56496(14) -0.0369(2) 0.0200(4) Uani 1 1 d . . .
H33 H 0.0727 0.4981 -0.0438 0.024 Uiso 1 1 calc R . .
O100 O 0.27702(6) 0.39226(12) 0.16048(19) 0.0335(4) Uani 1 1 d . . .
H100 H 0.2765 0.3833 0.2588 0.050 Uiso 1 1 d R . .
C100 C 0.31720(8) 0.34930(18) 0.1411(3) 0.0355(5) Uani 1 1 d . . .
H10E H 0.3179 0.3545 0.0291 0.053 Uiso 1 1 calc R . .
H10F H 0.3176 0.2824 0.1710 0.053 Uiso 1 1 calc R . .
H10G H 0.3439 0.3812 0.2097 0.053 Uiso 1 1 calc R . .
O110 O 0.04303(5) 0.12906(12) 0.41798(19) 0.0321(3) Uani 1 1 d . . .
H110 H 0.0188 0.1752 0.3949 0.048 Uiso 1 1 d R . .
C110 C 0.02930(9) 0.04508(19) 0.3326(3) 0.0399(6) Uani 1 1 d . . .
H11C H 0.0542 -0.0012 0.3605 0.060 Uiso 1 1 calc R . .
H11D H 0.0218 0.0582 0.2176 0.060 Uiso 1 1 calc R . .
H11E H 0.0024 0.0196 0.3600 0.060 Uiso 1 1 calc R . .
C120 C 0.0000 0.7932(3) 0.5000 0.0420(8) Uani 1 2 d S . .
H12C H -0.0118 0.7314 0.5119 0.050 Uiso 0.50 1 d PR A -1
H12G H -0.0233 0.8203 0.4140 0.050 Uiso 0.50 1 d PR A -1
H12H H 0.0018 0.8227 0.6012 0.050 Uiso 0.50 1 d PR A -1
O12A O 0.04051(15) 0.7736(3) 0.4698(5) 0.0476(9) Uani 0.50 1 d P B -1
H12I H 0.0396 0.7192 0.4302 0.071 Uiso 0.50 1 calc PR B -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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C11 O1 C12 115.17(16) .
C2 O2 C22 116.63(16) .
C3 O3 C23 116.97(15) .
C9 N1 C6 126.58(16) .
C9 N1 C8 119.09(15) .
C6 N1 C8 109.41(14) .
C16 N2 C15 112.23(15) .
C16 N2 C21 108.00(13) .
C15 N2 C21 113.77(14) .
C16 N2 H2 107.5 .
C15 N2 H2 107.5 .
C21 N2 H2 107.6 .
C2 C1 C6 117.27(17) .
C2 C1 H1 121.4 .
C6 C1 H1 121.4 .
O2 C2 C1 123.44(17) .
O2 C2 C3 114.96(17) .
C1 C2 C3 121.58(17) .
O3 C3 C4 124.80(17) .
O3 C3 C2 115.23(17) .
C4 C3 C2 119.96(17) .
C3 C4 C5 118.76(17) .
C3 C4 H4 120.6 .
C5 C4 H4 120.6 .
C6 C5 C4 120.49(16) .
C6 C5 C7 110.06(16) .
C4 C5 C7 129.05(17) .
C5 C6 C1 121.93(17) .
C5 C6 N1 110.34(16) .
C1 C6 N1 127.71(17) .
C5 C7 C21 116.86(16) .
C5 C7 C17 111.64(14) .
C21 C7 C17 101.97(14) .
C5 C7 C8 102.51(14) .
C21 C7 C8 113.84(14) .
C17 C7 C8 110.25(15) .
N1 C8 C18 106.22(14) .
N1 C8 C7 104.47(14) .
C18 C8 C7 117.29(16) .
N1 C8 H8 109.5 .
C18 C8 H8 109.5 .
C7 C8 H8 109.5 .
O4 C9 N1 122.78(18) .
O4 C9 C10 123.35(18) .
N1 C9 C10 113.86(16) .
C9 C10 C11 116.27(17) .
C9 C10 H10A 108.2 .
C11 C10 H10A 108.2 .
C9 C10 H10B 108.2 .
C11 C10 H10B 108.2 .
H10A C10 H10B 107.4 .
O1 C11 C10 102.50(16) .
O1 C11 C18 115.71(15) .
C10 C11 C18 110.68(15) .
O1 C11 H11 109.2 .
C10 C11 H11 109.2 .
C18 C11 H11 109.2 .
O1 C12 C13 109.44(16) .
O1 C12 H12A 109.8 .
C13 C12 H12A 109.8 .
O1 C12 H12B 109.8 .
C13 C12 H12B 109.8 .
H12A C12 H12B 108.2 .
C14 C13 C12 121.15(19) .
C14 C13 H13 119.4 .
C12 C13 H13 119.4 .
C13 C14 C15 122.42(18) .
C13 C14 C19 121.55(17) .
C15 C14 C19 116.01(16) .
C14 C15 N2 111.09(15) .
C14 C15 H15A 109.4 .
N2 C15 H15A 109.4 .
C14 C15 H15B 109.4 .
N2 C15 H15B 109.4 .
H15A C15 H15B 108.0 .
N2 C16 C17 104.39(15) .
N2 C16 H16A 110.9 .
C17 C16 H16A 110.9 .
N2 C16 H16B 110.9 .
C17 C16 H16B 110.9 .
H16A C16 H16B 108.9 .
C16 C17 C7 103.09(14) .
C16 C17 H17A 111.1 .
C7 C17 H17A 111.1 .
C16 C17 H17B 111.1 .
C7 C17 H17B 111.1 .
H17A C17 H17B 109.1 .
C8 C18 C19 112.34(15) .
C8 C18 C11 107.47(15) .
C19 C18 C11 118.85(15) .
C8 C18 H18 105.7 .
C19 C18 H18 105.7 .
C11 C18 H18 105.7 .
C14 C19 C18 113.97(16) .
C14 C19 C20 109.45(15) .
C18 C19 C20 107.07(15) .
C14 C19 H19 108.7 .
C18 C19 H19 108.7 .
C20 C19 H19 108.7 .
C21 C20 C19 108.80(15) .
C21 C20 H20A 109.9 .
C19 C20 H20A 109.9 .
C21 C20 H20B 109.9 .
C19 C20 H20B 109.9 .
H20A C20 H20B 108.3 .
C20 C21 N2 110.58(14) .
C20 C21 C7 115.63(15) .
N2 C21 C7 104.22(14) .
C20 C21 H21 108.7 .
N2 C21 H21 108.7 .
C7 C21 H21 108.7 .
O2 C22 H22A 109.5 .
O2 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
O2 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
O3 C23 H23A 109.5 .
O3 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
O3 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
C26 O7 H7 109.6 .
C27 N3 C25 121.03(16) .
C27 N3 H3 119.5 .
C25 N3 H3 119.4 .
O9 N4 O10 123.6(2) .
O9 N4 C30 118.3(2) .
O10 N4 C30 118.1(2) .
O11 N5 O12 124.3(2) .
O11 N5 C32 117.77(19) .
O12 N5 C32 117.85(18) .
O6 C24 O5 124.28(18) .
O6 C24 C25 119.63(17) .
O5 C24 C25 115.97(16) .
N3 C25 C26 110.80(15) .
N3 C25 C24 110.41(15) .
C26 C25 C24 115.24(16) .
N3 C25 H25 106.6 .
C26 C25 H25 106.6 .
C24 C25 H25 106.6 .
O7 C26 C25 112.34(15) .
O7 C26 H26A 109.1 .
C25 C26 H26A 109.1 .
O7 C26 H26B 109.1 .
C25 C26 H26B 109.1 .
H26A C26 H26B 107.9 .
O8 C27 N3 123.76(18) .
O8 C27 C28 120.03(17) .
N3 C27 C28 116.19(17) .
C33 C28 C29 119.61(19) .
C33 C28 C27 123.42(17) .
C29 C28 C27 116.97(18) .
C30 C29 C28 118.69(19) .
C30 C29 H29 120.7 .
C28 C29 H29 120.7 .
C31 C30 C29 123.32(19) .
C31 C30 N4 118.4(2) .
C29 C30 N4 118.3(2) .
C32 C31 C30 115.80(19) .
C32 C31 H31 122.1 .
C30 C31 H31 122.1 .
C33 C32 C31 123.6(2) .
C33 C32 N5 118.26(19) .
C31 C32 N5 118.06(19) .
C32 C33 C28 118.92(18) .
C32 C33 H33 120.5 .
C28 C33 H33 120.5 .
C100 O100 H100 107.3 .
O100 C100 H10E 109.5 .
O100 C100 H10F 109.5 .
H10E C100 H10F 109.5 .
O100 C100 H10G 109.5 .
H10E C100 H10G 109.5 .
H10F C100 H10G 109.5 .
C110 O110 H110 111.1 .
O110 C110 H11C 109.5 .
O110 C110 H11D 109.5 .
H11C C110 H11D 109.5 .
O110 C110 H11E 109.5 .
H11C C110 H11E 109.5 .
H11D C110 H11E 109.5 .
O12A C120 O12A 156.3(5) 2_556
O12A C120 H12C 53.7 2_556
O12A C120 H12C 102.6 .
O12A C120 H12G 73.3 2_556
O12A C120 H12G 116.8 .
H12C C120 H12G 103.2 .
O12A C120 H12H 75.3 2_556
O12A C120 H12H 115.6 .
H12C C120 H12H 103.2 .
H12G C120 H12H 112.8 .
C120 O12A H12I 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.433(2) .
O1 C12 1.435(2) .
O2 C2 1.378(2) .
O2 C22 1.433(3) .
O3 C3 1.372(2) .
O3 C23 1.431(3) .
O4 C9 1.227(2) .
N1 C9 1.363(2) .
N1 C6 1.417(2) .
N1 C8 1.479(2) .
N2 C16 1.509(3) .
N2 C15 1.513(2) .
N2 C21 1.538(2) .
N2 H2 0.9298 .
C1 C2 1.388(3) .
C1 C6 1.395(3) .
C1 H1 0.9500 .
C2 C3 1.407(3) .
C3 C4 1.391(3) .
C4 C5 1.392(3) .
C4 H4 0.9500 .
C5 C6 1.384(3) .
C5 C7 1.515(2) .
C7 C21 1.542(3) .
C7 C17 1.545(3) .
C7 C8 1.558(2) .
C8 C18 1.535(2) .
C8 H8 1.0000 .
C9 C10 1.518(3) .
C10 C11 1.543(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C18 1.544(3) .
C11 H11 1.0000 .
C12 C13 1.507(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.334(3) .
C13 H13 0.9500 .
C14 C15 1.499(3) .
C14 C19 1.522(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.519(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.538(2) .
C18 H18 1.0000 .
C19 C20 1.539(3) .
C19 H19 1.0000 .
C20 C21 1.519(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21 1.0000 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
O5 C24 1.274(2) .
O6 C24 1.239(2) .
O7 C26 1.421(2) .
O7 H7 0.8380 .
O8 C27 1.234(2) .
O9 N4 1.222(3) .
O10 N4 1.224(3) .
O11 N5 1.225(2) .
O12 N5 1.227(3) .
N3 C27 1.339(3) .
N3 C25 1.453(2) .
N3 H3 0.8799 .
N4 C30 1.465(3) .
N5 C32 1.474(3) .
C24 C25 1.539(3) .
C25 C26 1.527(3) .
C25 H25 1.0000 .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C27 C28 1.508(3) .
C28 C33 1.392(3) .
C28 C29 1.393(3) .
C29 C30 1.387(3) .
C29 H29 0.9500 .
C30 C31 1.383(3) .
C31 C32 1.380(3) .
C31 H31 0.9500 .
C32 C33 1.379(3) .
C33 H33 0.9500 .
O100 C100 1.414(3) .
O100 H100 0.8664 .
C100 H10E 0.9800 .
C100 H10F 0.9800 .
C100 H10G 0.9800 .
O110 C110 1.403(3) .
O110 H110 0.9632 .
C110 H11C 0.9800 .
C110 H11D 0.9800 .
C110 H11E 0.9800 .
C120 O12A 1.354(4) 2_556
C120 O12A 1.354(4) .
C120 H12C 0.9604 .
C120 H12G 0.9607 .
C120 H12H 0.9600 .
O12A H12I 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O5 0.93 1.73 2.659(2) 173.0 2_556
O7 H7 O110 0.84 2.07 2.842(2) 153.0 .
N3 H3 O6 0.88 1.98 2.841(2) 166.8 2
O100 H100 O3 0.87 2.25 2.964(2) 140.2 .
O100 H100 O2 0.87 2.31 3.093(2) 150.0 .
O110 H110 O5 0.96 1.76 2.700(2) 163.5 .
O12A H12I O8 0.84 1.98 2.821(4) 179.0 .
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
C22 O2 C2 C1 -13.7(3)
C22 O2 C2 C3 167.60(18)
C6 C1 C2 O2 -179.01(17)
C6 C1 C2 C3 -0.4(3)
C23 O3 C3 C4 9.1(3)
C23 O3 C3 C2 -171.92(17)
O2 C2 C3 O3 -0.2(2)
C1 C2 C3 O3 -178.96(16)
O2 C2 C3 C4 178.79(16)
C1 C2 C3 C4 0.1(3)
O3 C3 C4 C5 179.13(17)
C2 C3 C4 C5 0.2(3)
C3 C4 C5 C6 -0.2(3)
C3 C4 C5 C7 -172.18(18)
C4 C5 C6 C1 -0.2(3)
C7 C5 C6 C1 173.22(17)
C4 C5 C6 N1 -178.99(16)
C7 C5 C6 N1 -5.6(2)
C2 C1 C6 C5 0.5(3)
C2 C1 C6 N1 179.04(17)
C9 N1 C6 C5 -161.25(18)
C8 N1 C6 C5 -6.6(2)
C9 N1 C6 C1 20.0(3)
C8 N1 C6 C1 174.68(18)
C6 C5 C7 C21 139.69(17)
C4 C5 C7 C21 -47.6(3)
C6 C5 C7 C17 -103.50(18)
C4 C5 C7 C17 69.2(2)
C6 C5 C7 C8 14.49(19)
C4 C5 C7 C8 -172.81(18)
C9 N1 C8 C18 47.6(2)
C6 N1 C8 C18 -109.26(16)
C9 N1 C8 C7 172.18(16)
C6 N1 C8 C7 15.36(19)
C5 C7 C8 N1 -17.45(18)
C21 C7 C8 N1 -144.61(15)
C17 C7 C8 N1 101.53(16)
C5 C7 C8 C18 99.78(17)
C21 C7 C8 C18 -27.4(2)
C17 C7 C8 C18 -141.24(16)
C6 N1 C9 O4 -20.2(3)
C8 N1 C9 O4 -172.69(19)
C6 N1 C9 C10 161.37(18)
C8 N1 C9 C10 8.9(2)
O4 C9 C10 C11 137.1(2)
N1 C9 C10 C11 -44.5(2)
C12 O1 C11 C10 176.51(15)
C12 O1 C11 C18 -63.0(2)
C9 C10 C11 O1 142.61(16)
C9 C10 C11 C18 18.7(2)
C11 O1 C12 C13 90.3(2)
O1 C12 C13 C14 -68.2(2)
C12 C13 C14 C15 178.23(17)
C12 C13 C14 C19 -3.6(3)
C13 C14 C15 N2 -131.46(19)
C19 C14 C15 N2 50.3(2)
C16 N2 C15 C14 78.34(19)
C21 N2 C15 C14 -44.7(2)
C15 N2 C16 C17 -142.55(15)
C21 N2 C16 C17 -16.34(18)
N2 C16 C17 C7 36.75(18)
C5 C7 C17 C16 -168.53(16)
C21 C7 C17 C16 -43.02(17)
C8 C7 C17 C16 78.21(18)
N1 C8 C18 C19 157.33(15)
C7 C8 C18 C19 41.0(2)
N1 C8 C18 C11 -70.11(18)
C7 C8 C18 C11 173.61(15)
O1 C11 C18 C8 -79.72(19)
C10 C11 C18 C8 36.3(2)
O1 C11 C18 C19 49.2(2)
C10 C11 C18 C19 165.21(17)
C13 C14 C19 C18 62.5(2)
C15 C14 C19 C18 -119.19(17)
C13 C14 C19 C20 -177.64(17)
C15 C14 C19 C20 0.6(2)
C8 C18 C19 C14 61.0(2)
C11 C18 C19 C14 -65.6(2)
C8 C18 C19 C20 -60.1(2)
C11 C18 C19 C20 173.21(16)
C14 C19 C20 C21 -56.56(19)
C18 C19 C20 C21 67.43(18)
C19 C20 C21 N2 61.77(19)
C19 C20 C21 C7 -56.3(2)
C16 N2 C21 C20 -135.31(15)
C15 N2 C21 C20 -10.0(2)
C16 N2 C21 C7 -10.42(18)
C15 N2 C21 C7 114.87(16)
C5 C7 C21 C20 -84.0(2)
C17 C7 C21 C20 154.03(15)
C8 C7 C21 C20 35.3(2)
C5 C7 C21 N2 154.44(15)
C17 C7 C21 N2 32.44(17)
C8 C7 C21 N2 -86.27(17)
C27 N3 C25 C26 -95.0(2)
C27 N3 C25 C24 136.05(18)
O6 C24 C25 N3 -21.7(2)
O5 C24 C25 N3 162.12(15)
O6 C24 C25 C26 -148.16(17)
O5 C24 C25 C26 35.7(2)
N3 C25 C26 O7 -63.0(2)
C24 C25 C26 O7 63.3(2)
C25 N3 C27 O8 -2.3(3)
C25 N3 C27 C28 179.13(15)
O8 C27 C28 C33 167.05(18)
N3 C27 C28 C33 -14.3(3)
O8 C27 C28 C29 -13.6(3)
N3 C27 C28 C29 165.03(17)
C33 C28 C29 C30 2.0(3)
C27 C28 C29 C30 -177.42(16)
C28 C29 C30 C31 -2.3(3)
C28 C29 C30 N4 177.77(18)
O9 N4 C30 C31 -174.5(2)
O10 N4 C30 C31 5.4(3)
O9 N4 C30 C29 5.5(3)
O10 N4 C30 C29 -174.65(19)
C29 C30 C31 C32 0.5(3)
N4 C30 C31 C32 -179.51(19)
C30 C31 C32 C33 1.6(3)
C30 C31 C32 N5 -175.42(17)
O11 N5 C32 C33 -165.65(18)
O12 N5 C32 C33 11.8(3)
O11 N5 C32 C31 11.5(3)
O12 N5 C32 C31 -171.05(19)
C31 C32 C33 C28 -1.8(3)
N5 C32 C33 C28 175.15(16)
C29 C28 C33 C32 0.0(3)
C27 C28 C33 C32 179.31(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146347
