#------------------------------------------------------------------------------
#$Date: 2020-09-26 08:12:25 +0300 (Sat, 26 Sep 2020) $
#$Revision: 256796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/36/2243603.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_2243603
loop_
_publ_author_name
'Nguyen, Xuan Tu'
'Le, Thuy Quynh'
'Bui Thi, Tra My'
'Mac, Dinh Hung'
'Bui, Thai Thanh Thu'
_publ_section_title
;
 Synthesis and crystal structure of peptide dimethyl biphenyl hybrid
 C₅₂H₆₀N₆O₁₀·0.25H₂O
;
_journal_coeditor_code           VM2240
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1675
_journal_page_last               1678
_journal_paper_doi               10.1107/S2056989020012931
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration R
_chemical_formula_iupac          'C52 H60 N6 O10, 0.25H2 O'
_chemical_formula_moiety         'C52 H60 N6 O10, 0.25(H2 O)'
_chemical_formula_sum            'C52 H60.5 N6 O10.25'
_chemical_formula_weight         933.56
_chemical_name_systematic
'Dimethyl 2,2'-[((2S,2'S)-2,2'-{[(2S,2'S)-1,1'-(6,6'-dimethyl-[1,1'-biphenyl]-2,2'-dicarbonyl)bis(pyrrolidine-1,2-diyl-2-carbonyl)]bis(azanediyl)}bis(3-phenylpropanoyl))bis(azanediyl)](2S,2'S)-dipropionate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.999(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.505(3)
_cell_length_b                   12.3814(12)
_cell_length_c                   14.6346(14)
_cell_measurement_reflns_used    9371
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.747
_cell_measurement_theta_min      2.792
_cell_volume                     4908.1(9)
_computing_cell_refinement
;
SAINT (Bruker, 2013)
;
_computing_data_collection
;
APEX22 (Bruker 2013)
;
_computing_data_reduction
;
SAINT (Bruker, 2013)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
ShelXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            84318
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.747
_diffrn_reflns_theta_min         2.792
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.7130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS-; Bruker, 2013)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       needle
_exptl_crystal_F_000             1986
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.157
_refine_ls_abs_structure_details
;
Flack x determined using 3323 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         9371
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0381
_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)+(0.0359P)²+2.1291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                7959
_reflns_number_total             9371
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2240sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        4908.2(8)
_cod_original_formula_sum        'C52 H60.50 N6 O10.25'
_cod_database_code               2243603
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 O5 0.33318(6) 0.37671(15) 0.30911(12) 0.0262(4) Uani d 1 . .
O O4 0.25033(7) 0.41245(17) 0.49754(15) 0.0367(5) Uani d 1 . .
O O6 0.37283(7) 0.35432(16) 0.07943(13) 0.0314(4) Uani d 1 . .
N N3 0.36969(8) 0.32535(18) 0.45153(14) 0.0252(5) Uani d 1 . .
N N2 0.32176(8) 0.50351(19) 0.50273(15) 0.0291(5) Uani d 1 . .
H H2 0.3537 0.4960 0.5038 0.035 Uiso calc 1 . .
O O7 0.25946(8) 0.5451(2) -0.00116(15) 0.0531(6) Uani d 1 . .
O O3 0.38550(8) 0.64671(17) 0.4803(2) 0.0552(7) Uani d 1 . .
O O9 0.40799(7) 0.7684(2) 0.02936(16) 0.0536(7) Uani d 1 . .
N N1 0.33544(8) 0.7906(2) 0.48045(17) 0.0351(6) Uani d 1 . .
H H1 0.3070 0.8150 0.4917 0.042 Uiso calc 1 . .
N N5 0.29721(8) 0.50901(18) 0.14594(15) 0.0277(5) Uani d 1 . .
H H5 0.3085 0.4583 0.1862 0.033 Uiso calc 1 . .
N N4 0.29975(8) 0.2897(2) 0.10755(15) 0.0302(5) Uani d 1 . .
O O2A 0.4152(8) 0.8404(16) 0.5865(9) 0.052(4) Uani d 0.498(6) A 1
O O10 0.47865(9) 0.8022(2) 0.12726(19) 0.0665(8) Uani d 1 . .
C C19 0.37162(9) 0.35712(19) 0.36445(17) 0.0221(5) Uani d 1 . .
O O8 0.36763(10) 0.74704(19) 0.2248(2) 0.0667(8) Uani d 1 . .
N N6 0.38529(8) 0.6049(2) 0.14123(16) 0.0335(5) Uani d 1 . .
H H6 0.3742 0.5463 0.1106 0.040 Uiso calc 1 . .
C C20 0.42128(9) 0.3761(2) 0.33809(17) 0.0224(5) Uani d 1 . .
C C14 0.29481(10) 0.4139(2) 0.49355(18) 0.0277(6) Uani d 1 . .
C C22 0.49273(10) 0.4901(2) 0.34994(19) 0.0300(6) Uani d 1 . .
H H22 0.5116 0.5499 0.3769 0.036 Uiso calc 1 . .
C C21 0.44813(10) 0.4663(2) 0.37539(19) 0.0264(6) Uani d 1 . .
H H21 0.4355 0.5113 0.4184 0.032 Uiso calc 1 . .
C C39 0.27589(10) 0.4803(3) 0.05996(19) 0.0336(7) Uani d 1 . .
C C34 0.34964(10) 0.2867(2) 0.11713(18) 0.0292(6) Uani d 1 . .
C C25 0.43896(10) 0.3099(2) 0.27349(17) 0.0264(6) Uani d 1 . .
C C15 0.32173(10) 0.3090(2) 0.48016(18) 0.0290(6) Uani d 1 . .
H H15 0.3004 0.2638 0.4327 0.035 Uiso calc 1 . .
C C23 0.50992(10) 0.4261(2) 0.2846(2) 0.0339(7) Uani d 1 . .
H H23 0.5403 0.4441 0.2659 0.041 Uiso calc 1 . .
C C32 0.37479(11) 0.1926(2) 0.1698(2) 0.0342(7) Uani d 1 . .
C C5 0.34545(10) 0.6858(2) 0.4894(2) 0.0362(7) Uani d 1 . .
C C42 0.22491(12) 0.6148(3) 0.2431(2) 0.0393(7) Uani d 1 . .
C C8 0.32288(11) 0.5941(3) 0.6886(2) 0.0368(7) Uani d 1 . .
C C18 0.41107(10) 0.2861(3) 0.52286(19) 0.0355(7) Uani d 1 . .
H H18A 0.4391 0.3375 0.5316 0.043 Uiso calc 1 . .
H H18B 0.4228 0.2143 0.5062 0.043 Uiso calc 1 . .
C C24 0.48386(10) 0.3365(2) 0.24582(19) 0.0326(7) Uani d 1 . .
C C6 0.30370(9) 0.6123(2) 0.5111(2) 0.0303(6) Uani d 1 . .
H H6A 0.2743 0.6231 0.4612 0.036 Uiso calc 1 . .
C C28 0.43711(12) 0.1101(2) 0.2858(2) 0.0382(7) Uani d 1 . .
C C38 0.27062(10) 0.3606(3) 0.03950(19) 0.0348(7) Uani d 1 . .
H H38 0.2789 0.3459 -0.0232 0.042 Uiso calc 1 . .
C C27 0.41520(10) 0.2032(2) 0.2421(2) 0.0306(6) Uani d 1 . .
C C7 0.28776(10) 0.6356(3) 0.6048(2) 0.0360(7) Uani d 1 . .
H H7A 0.2831(11) 0.715(3) 0.610(2) 0.043 Uiso d 1 . .
H H7B 0.2561(12) 0.604(3) 0.606(2) 0.043 Uiso d 1 . .
C C40 0.30215(11) 0.6212(2) 0.1744(2) 0.0344(7) Uani d 1 . .
H H40 0.2820 0.6644 0.1237 0.041 Uiso calc 1 . .
C C48 0.35480(12) 0.6626(2) 0.1841(2) 0.0395(7) Uani d 1 . .
C C51 0.44291(12) 0.7469(3) 0.1020(2) 0.0465(8) Uani d 1 . .
C C41 0.27949(12) 0.6391(2) 0.2612(2) 0.0403(7) Uani d 1 . .
H H41A 0.2962 0.5918 0.3116 0.048 Uiso calc 1 . .
H H41B 0.2848 0.7150 0.2818 0.048 Uiso calc 1 . .
C C49 0.43632(11) 0.6369(3) 0.1441(2) 0.0381(7) Uani d 1 . .
H H49 0.4534 0.6375 0.2103 0.046 Uiso calc 1 . .
C C31 0.35836(13) 0.0900(2) 0.1390(2) 0.0456(8) Uani d 1 . .
H H31 0.3315 0.0830 0.0888 0.055 Uiso calc 1 . .
C C17 0.38721(11) 0.2796(3) 0.6093(2) 0.0461(8) Uani d 1 . .
H H17A 0.3879 0.3506 0.6406 0.055 Uiso calc 1 . .
H H17B 0.4040 0.2256 0.6538 0.055 Uiso calc 1 . .
C C43 0.20546(13) 0.5304(3) 0.2867(2) 0.0406(8) Uani d 1 . .
H H43 0.2267 0.4876 0.3304 0.049 Uiso calc 1 . .
C C26 0.50273(12) 0.2713(3) 0.1714(2) 0.0459(8) Uani d 1 . .
H H26A 0.5078 0.1962 0.1920 0.069 Uiso calc 1 . .
H H26B 0.5341 0.3018 0.1604 0.069 Uiso calc 1 . .
H H26C 0.4785 0.2737 0.1139 0.069 Uiso calc 1 . .
C C35 0.26820(12) 0.2261(3) 0.1605(2) 0.0403(8) Uani d 1 . .
H H35A 0.2818 0.2267 0.2278 0.048 Uiso calc 1 . .
H H35B 0.2648 0.1504 0.1386 0.048 Uiso calc 1 . .
C C9 0.36689(11) 0.6476(3) 0.7211(3) 0.0515(9) Uani d 1 . .
H H9 0.3753 0.7096 0.6890 0.062 Uiso calc 1 . .
C C30 0.38083(14) -0.0007(3) 0.1809(3) 0.0563(10) Uani d 1 . .
H H30 0.3697 -0.0703 0.1592 0.068 Uiso calc 1 . .
C C36 0.21906(12) 0.2852(3) 0.1399(2) 0.0492(9) Uani d 1 . .
H H36A 0.2182 0.3463 0.1833 0.059 Uiso calc 1 . .
H H36B 0.1912 0.2358 0.1441 0.059 Uiso calc 1 . .
C C44 0.15538(13) 0.5070(3) 0.2676(2) 0.0488(9) Uani d 1 . .
H H44 0.1427 0.4490 0.2990 0.059 Uiso calc 1 . .
C C16 0.33427(11) 0.2449(3) 0.5705(2) 0.0434(8) Uani d 1 . .
H H16A 0.3324 0.1662 0.5584 0.052 Uiso calc 1 . .
H H16B 0.3117 0.2637 0.6138 0.052 Uiso calc 1 . .
C C29 0.41922(14) 0.0090(3) 0.2539(2) 0.0520(9) Uani d 1 . .
H H29 0.4339 -0.0543 0.2834 0.062 Uiso calc 1 . .
C C33 0.48036(13) 0.1160(3) 0.3656(2) 0.0466(8) Uani d 1 . .
H H33A 0.5112 0.1201 0.3410 0.070 Uiso calc 1 . .
H H33B 0.4807 0.0514 0.4044 0.070 Uiso calc 1 . .
H H33C 0.4771 0.1804 0.4030 0.070 Uiso calc 1 . .
C C37 0.21720(11) 0.3253(3) 0.0408(2) 0.0492(9) Uani d 1 . .
H H37A 0.1941 0.3867 0.0268 0.059 Uiso calc 1 . .
H H37B 0.2070 0.2668 -0.0047 0.059 Uiso calc 1 . .
C C50 0.46145(12) 0.5544(3) 0.0915(2) 0.0498(9) Uani d 1 . .
H H50A 0.4560 0.4818 0.1145 0.075 Uiso calc 1 . .
H H50B 0.4970 0.5693 0.1008 0.075 Uiso calc 1 . .
H H50C 0.4476 0.5587 0.0252 0.075 Uiso calc 1 . .
C C13 0.31123(13) 0.5060(3) 0.7362(2) 0.0546(9) Uani d 1 . .
H H13 0.2811 0.4689 0.7158 0.065 Uiso calc 1 . .
C C3 0.37093(12) 0.8660(3) 0.4522(3) 0.0506(9) Uani d 1 . .
H H3A 0.3893 0.8282 0.4082 0.061 Uiso calc 0.498(6) A 1
H H3B 0.3776 0.8469 0.3891 0.061 Uiso calc 0.502(6) A 2
C C45 0.12403(14) 0.5668(3) 0.2040(3) 0.0587(10) Uani d 1 . .
H H45 0.0898 0.5502 0.1903 0.070 Uiso calc 1 . .
C C47 0.19287(15) 0.6750(4) 0.1803(3) 0.0668(12) Uani d 1 . .
H H47 0.2053 0.7342 0.1500 0.080 Uiso calc 1 . .
C C52 0.41693(14) 0.8637(4) -0.0232(3) 0.0722(13) Uani d 1 . .
H H52A 0.3905 0.8713 -0.0770 0.108 Uiso calc 1 . .
H H52B 0.4487 0.8563 -0.0443 0.108 Uiso calc 1 . .
H H52C 0.4177 0.9278 0.0163 0.108 Uiso calc 1 . .
C C11 0.38662(15) 0.5233(4) 0.8454(3) 0.0675(12) Uani d 1 . .
H H11 0.4085 0.4988 0.8989 0.081 Uiso calc 1 . .
C C10 0.39836(14) 0.6128(4) 0.7984(3) 0.0665(12) Uani d 1 . .
H H10 0.4283 0.6505 0.8195 0.080 Uiso calc 1 . .
C C12 0.34359(16) 0.4694(4) 0.8155(3) 0.0695(12) Uani d 1 . .
H H12 0.3354 0.4074 0.8480 0.083 Uiso calc 1 . .
C C46 0.14300(16) 0.6512(4) 0.1605(3) 0.0794(14) Uani d 1 . .
H H46 0.1217 0.6935 0.1164 0.095 Uiso calc 1 . .
O O1B 0.46376(18) 0.8694(5) 0.5125(5) 0.082(2) Uani d 0.502(6) A 2
C C1A 0.4577(7) 0.8657(13) 0.6565(10) 0.065(4) Uani d 0.498(6) A 1
H H1AA 0.4865 0.8781 0.6266 0.098 Uiso calc 0.498(6) A 1
H H1AB 0.4645 0.8052 0.7000 0.098 Uiso calc 0.498(6) A 1
H H1AC 0.4510 0.9308 0.6902 0.098 Uiso calc 0.498(6) A 1
C C4A 0.3372(3) 0.9666(6) 0.3947(6) 0.0338(16) Uani d 0.498(6) A 1
H H4AA 0.314(3) 1.001(6) 0.437(5) 0.051 Uiso d 0.498(6) A 1
H H4AB 0.318(3) 0.951(6) 0.348(5) 0.051 Uiso d 0.498(6) A 1
H H4AC 0.365(3) 1.022(6) 0.380(5) 0.051 Uiso d 0.498(6) A 1
C C2B 0.4233(4) 0.8525(9) 0.5327(8) 0.051(3) Uani d 0.502(6) A 2
O O11 0.2727(2) 0.8908(5) 0.1778(4) 0.0166(14) Uani d 0.25 . .
H H11A 0.3048 0.8916 0.1906 0.025 Uiso d 0.25 . .
H H11B 0.2657 0.8381 0.1383 0.025 Uiso d 0.25 . .
C C4B 0.3574(3) 0.9738(5) 0.4551(7) 0.049(2) Uani d 0.502(6) A 2
H H4BA 0.3299 0.9887 0.4044 0.074 Uiso calc 0.502(6) A 2
H H4BB 0.3856 1.0197 0.4483 0.074 Uiso calc 0.502(6) A 2
H H4BC 0.3471 0.9891 0.5146 0.074 Uiso calc 0.502(6) A 2
C C2A 0.4049(2) 0.9141(6) 0.5214(4) 0.0317(15) Uani d 0.498(6) A 1
O O2B 0.4184(6) 0.8407(16) 0.6190(9) 0.044(3) Uani d 0.502(6) A 2
O O1A 0.42431(16) 1.0015(3) 0.5223(3) 0.0492(16) Uani d 0.498(6) A 1
C C1B 0.4595(6) 0.8377(14) 0.6925(11) 0.081(5) Uani d 0.502(6) A 2
H H1BA 0.4832 0.7835 0.6788 0.121 Uiso calc 0.502(6) A 2
H H1BB 0.4483 0.8188 0.7504 0.121 Uiso calc 0.502(6) A 2
H H1BC 0.4754 0.9088 0.6989 0.121 Uiso calc 0.502(6) A 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_
_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
C19 N3 C15 . . 119.8(2) ?
C19 N3 C18 . . 127.6(2) ?
C15 N3 C18 . . 111.8(2) ?
C14 N2 H2 . . 116.9 ?
C14 N2 C6 . . 126.3(2) ?
C6 N2 H2 . . 116.9 ?
C51 O9 C52 . . 114.9(3) ?
C5 N1 H1 . . 119.5 ?
C5 N1 C3 . . 121.0(2) ?
C3 N1 H1 . . 119.5 ?
C39 N5 H5 . . 119.1 ?
C39 N5 C40 . . 121.9(2) ?
C40 N5 H5 . . 119.1 ?
C34 N4 C38 . . 120.9(2) ?
C34 N4 C35 . . 127.2(3) ?
C38 N4 C35 . . 112.0(2) ?
C2A O2A C1A . . 114.1(14) ?
O5 C19 N3 . . 120.5(2) ?
O5 C19 C20 . . 120.8(2) ?
N3 C19 C20 . . 118.5(2) ?
C48 N6 H6 . . 119.3 ?
C48 N6 C49 . . 121.5(3) ?
C49 N6 H6 . . 119.3 ?
C21 C20 C19 . . 117.9(2) ?
C21 C20 C25 . . 120.6(2) ?
C25 C20 C19 . . 121.3(2) ?
O4 C14 N2 . . 123.2(3) ?
O4 C14 C15 . . 120.1(2) ?
N2 C14 C15 . . 116.7(2) ?
C21 C22 H22 . . 120.3 ?
C21 C22 C23 . . 119.4(3) ?
C23 C22 H22 . . 120.3 ?
C20 C21 H21 . . 119.9 ?
C22 C21 C20 . . 120.1(3) ?
C22 C21 H21 . . 119.9 ?
O7 C39 N5 . . 123.8(3) ?
O7 C39 C38 . . 119.0(3) ?
N5 C39 C38 . . 117.2(2) ?
O6 C34 N4 . . 121.7(3) ?
O6 C34 C32 . . 121.8(2) ?
N4 C34 C32 . . 116.3(3) ?
C20 C25 C24 . . 118.9(2) ?
C20 C25 C27 . . 122.3(2) ?
C24 C25 C27 . . 118.3(2) ?
N3 C15 C14 . . 113.6(2) ?
N3 C15 H15 . . 109.1 ?
N3 C15 C16 . . 103.9(2) ?
C14 C15 H15 . . 109.1 ?
C14 C15 C16 . . 111.9(2) ?
C16 C15 H15 . . 109.1 ?
C22 C23 H23 . . 119.2 ?
C22 C23 C24 . . 121.7(3) ?
C24 C23 H23 . . 119.2 ?
C27 C32 C34 . . 123.4(2) ?
C31 C32 C34 . . 116.5(3) ?
C31 C32 C27 . . 120.0(3) ?
O3 C5 N1 . . 123.2(3) ?
O3 C5 C6 . . 120.2(3) ?
N1 C5 C6 . . 116.6(2) ?
C43 C42 C41 . . 121.6(3) ?
C47 C42 C41 . . 120.7(3) ?
C47 C42 C43 . . 117.7(3) ?
C9 C8 C7 . . 120.8(3) ?
C13 C8 C7 . . 120.8(3) ?
C13 C8 C9 . . 118.3(3) ?
N3 C18 H18A . . 111.3 ?
N3 C18 H18B . . 111.3 ?
N3 C18 C17 . . 102.3(2) ?
H18A C18 H18B . . 109.2 ?
C17 C18 H18A . . 111.3 ?
C17 C18 H18B . . 111.3 ?
C25 C24 C26 . . 120.6(3) ?
C23 C24 C25 . . 119.2(3) ?
C23 C24 C26 . . 120.2(3) ?
N2 C6 C5 . . 104.6(2) ?
N2 C6 H6A . . 107.9 ?
N2 C6 C7 . . 113.9(3) ?
C5 C6 H6A . . 107.9 ?
C7 C6 C5 . . 114.3(2) ?
C7 C6 H6A . . 107.9 ?
C27 C28 C33 . . 121.9(3) ?
C29 C28 C27 . . 119.1(3) ?
C29 C28 C33 . . 119.0(3) ?
N4 C38 C39 . . 115.6(2) ?
N4 C38 H38 . . 109.3 ?
N4 C38 C37 . . 103.5(3) ?
C39 C38 H38 . . 109.3 ?
C39 C38 C37 . . 109.6(2) ?
C37 C38 H38 . . 109.3 ?
C32 C27 C25 . . 123.8(2) ?
C32 C27 C28 . . 119.2(3) ?
C28 C27 C25 . . 116.9(2) ?
C8 C7 C6 . . 114.8(2) ?
C8 C7 H7A . . 110.1(19) ?
C8 C7 H7B . . 107.6(19) ?
C6 C7 H7A . . 108.4(19) ?
C6 C7 H7B . . 109.5(19) ?
H7A C7 H7B . . 106(3) ?
N5 C40 H40 . . 106.6 ?
N5 C40 C48 . . 113.0(2) ?
N5 C40 C41 . . 110.3(2) ?
C48 C40 H40 . . 106.6 ?
C48 C40 C41 . . 113.2(3) ?
C41 C40 H40 . . 106.6 ?
O8 C48 N6 . . 122.2(3) ?
O8 C48 C40 . . 121.5(3) ?
N6 C48 C40 . . 116.2(3) ?
O9 C51 C49 . . 112.6(3) ?
O10 C51 O9 . . 124.8(3) ?
O10 C51 C49 . . 122.3(3) ?
C42 C41 C40 . . 111.3(3) ?
C42 C41 H41A . . 109.4 ?
C42 C41 H41B . . 109.4 ?
C40 C41 H41A . . 109.4 ?
C40 C41 H41B . . 109.4 ?
H41A C41 H41B . . 108.0 ?
N6 C49 C51 . . 114.6(2) ?
N6 C49 H49 . . 108.6 ?
N6 C49 C50 . . 108.9(3) ?
C51 C49 H49 . . 108.6 ?
C50 C49 C51 . . 107.5(3) ?
C50 C49 H49 . . 108.6 ?
C32 C31 H31 . . 119.9 ?
C30 C31 C32 . . 120.2(3) ?
C30 C31 H31 . . 119.9 ?
C18 C17 H17A . . 111.2 ?
C18 C17 H17B . . 111.2 ?
C18 C17 C16 . . 103.0(2) ?
H17A C17 H17B . . 109.1 ?
C16 C17 H17A . . 111.2 ?
C16 C17 H17B . . 111.2 ?
C42 C43 H43 . . 119.4 ?
C42 C43 C44 . . 121.1(3) ?
C44 C43 H43 . . 119.4 ?
C24 C26 H26A . . 109.5 ?
C24 C26 H26B . . 109.5 ?
C24 C26 H26C . . 109.5 ?
H26A C26 H26B . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N4 C35 H35A . . 111.2 ?
N4 C35 H35B . . 111.2 ?
N4 C35 C36 . . 102.8(3) ?
H35A C35 H35B . . 109.1 ?
C36 C35 H35A . . 111.2 ?
C36 C35 H35B . . 111.2 ?
C8 C9 H9 . . 119.3 ?
C10 C9 C8 . . 121.4(4) ?
C10 C9 H9 . . 119.3 ?
C31 C30 H30 . . 119.9 ?
C29 C30 C31 . . 120.2(3) ?
C29 C30 H30 . . 119.9 ?
C35 C36 H36A . . 111.1 ?
C35 C36 H36B . . 111.1 ?
C35 C36 C37 . . 103.1(2) ?
H36A C36 H36B . . 109.1 ?
C37 C36 H36A . . 111.1 ?
C37 C36 H36B . . 111.1 ?
C43 C44 H44 . . 119.7 ?
C45 C44 C43 . . 120.6(3) ?
C45 C44 H44 . . 119.7 ?
C15 C16 C17 . . 103.5(2) ?
C15 C16 H16A . . 111.1 ?
C15 C16 H16B . . 111.1 ?
C17 C16 H16A . . 111.1 ?
C17 C16 H16B . . 111.1 ?
H16A C16 H16B . . 109.0 ?
C28 C29 H29 . . 119.4 ?
C30 C29 C28 . . 121.2(3) ?
C30 C29 H29 . . 119.4 ?
C28 C33 H33A . . 109.5 ?
C28 C33 H33B . . 109.5 ?
C28 C33 H33C . . 109.5 ?
H33A C33 H33B . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C38 C37 H37A . . 111.1 ?
C38 C37 H37B . . 111.1 ?
C36 C37 C38 . . 103.3(2) ?
C36 C37 H37A . . 111.1 ?
C36 C37 H37B . . 111.1 ?
H37A C37 H37B . . 109.1 ?
C49 C50 H50A . . 109.5 ?
C49 C50 H50B . . 109.5 ?
C49 C50 H50C . . 109.5 ?
H50A C50 H50B . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
C8 C13 H13 . . 119.7 ?
C8 C13 C12 . . 120.5(3) ?
C12 C13 H13 . . 119.7 ?
N1 C3 H3A . . 108.7 ?
N1 C3 H3B . . 110.4 ?
N1 C3 C4A . . 106.0(3) ?
N1 C3 C2B . . 105.5(4) ?
C4A C3 H3A . . 108.7 ?
C2B C3 H3B . . 110.4 ?
C4B C3 N1 . . 114.2(4) ?
C4B C3 H3B . . 110.4 ?
C4B C3 C2B . . 105.8(6) ?
C2A C3 N1 . . 117.8(4) ?
C2A C3 H3A . . 108.7 ?
C2A C3 C4A . . 106.8(5) ?
C44 C45 H45 . . 120.6 ?
C44 C45 C46 . . 118.8(4) ?
C46 C45 H45 . . 120.6 ?
C42 C47 H47 . . 119.3 ?
C42 C47 C46 . . 121.3(4) ?
C46 C47 H47 . . 119.3 ?
O9 C52 H52A . . 109.5 ?
O9 C52 H52B . . 109.5 ?
O9 C52 H52C . . 109.5 ?
H52A C52 H52B . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C10 C11 H11 . . 120.0 ?
C12 C11 H11 . . 120.0 ?
C12 C11 C10 . . 120.1(4) ?
C9 C10 C11 . . 119.9(4) ?
C9 C10 H10 . . 120.1 ?
C11 C10 H10 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C11 C12 C13 . . 119.8(4) ?
C11 C12 H12 . . 120.1 ?
C45 C46 C47 . . 120.5(4) ?
C45 C46 H46 . . 119.7 ?
C47 C46 H46 . . 119.7 ?
O2A C1A H1AA . . 109.5 ?
O2A C1A H1AB . . 109.5 ?
O2A C1A H1AC . . 109.5 ?
H1AA C1A H1AB . . 109.5 ?
H1AA C1A H1AC . . 109.5 ?
H1AB C1A H1AC . . 109.5 ?
C3 C4A H4AA . . 110(4) ?
C3 C4A H4AB . . 117(5) ?
C3 C4A H4AC . . 102(4) ?
H4AA C4A H4AB . . 102(6) ?
H4AA C4A H4AC . . 113(5) ?
H4AB C4A H4AC . . 112(7) ?
O1B C2B C3 . . 120.9(9) ?
O1B C2B O2B . . 120.6(13) ?
O2B C2B C3 . . 117.7(9) ?
H11A O11 H11B . . 104.4 ?
C3 C4B H4BA . . 109.5 ?
C3 C4B H4BB . . 109.5 ?
C3 C4B H4BC . . 109.5 ?
H4BA C4B H4BB . . 109.5 ?
H4BA C4B H4BC . . 109.5 ?
H4BB C4B H4BC . . 109.5 ?
O2A C2A C3 . . 105.3(9) ?
O1A C2A O2A . . 125.2(10) ?
O1A C2A C3 . . 129.3(6) ?
C2B O2B C1B . . 122.3(15) ?
O2B C1B H1BA . . 109.5 ?
O2B C1B H1BB . . 109.5 ?
O2B C1B H1BC . . 109.5 ?
H1BA C1B H1BB . . 109.5 ?
H1BA C1B H1BC . . 109.5 ?
H1BB C1B H1BC . . 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
O5 C19 . 1.239(3) ?
O4 C14 . 1.235(3) ?
O6 C34 . 1.239(3) ?
N3 C19 . 1.343(3) ?
N3 C15 . 1.466(3) ?
N3 C18 . 1.486(3) ?
N2 H2 . 0.8800 ?
N2 C14 . 1.328(3) ?
N2 C6 . 1.449(4) ?
O7 C39 . 1.228(4) ?
O3 C5 . 1.232(3) ?
O9 C51 . 1.330(4) ?
O9 C52 . 1.452(4) ?
N1 H1 . 0.8800 ?
N1 C5 . 1.329(4) ?
N1 C3 . 1.461(4) ?
N5 H5 . 0.8800 ?
N5 C39 . 1.341(4) ?
N5 C40 . 1.450(4) ?
N4 C34 . 1.355(3) ?
N4 C38 . 1.459(4) ?
N4 C35 . 1.486(4) ?
O2A C1A . 1.449(14) ?
O2A C2A . 1.314(15) ?
O10 C51 . 1.203(4) ?
C19 C20 . 1.501(4) ?
O8 C48 . 1.225(4) ?
N6 H6 . 0.8800 ?
N6 C48 . 1.338(4) ?
N6 C49 . 1.452(4) ?
C20 C21 . 1.397(4) ?
C20 C25 . 1.401(4) ?
C14 C15 . 1.524(4) ?
C22 H22 . 0.9500 ?
C22 C21 . 1.375(4) ?
C22 C23 . 1.387(4) ?
C21 H21 . 0.9500 ?
C39 C38 . 1.513(5) ?
C34 C32 . 1.498(4) ?
C25 C24 . 1.404(4) ?
C25 C27 . 1.510(4) ?
C15 H15 . 1.0000 ?
C15 C16 . 1.529(4) ?
C23 H23 . 0.9500 ?
C23 C24 . 1.388(4) ?
C32 C27 . 1.402(4) ?
C32 C31 . 1.396(4) ?
C5 C6 . 1.540(4) ?
C42 C41 . 1.509(5) ?
C42 C43 . 1.379(4) ?
C42 C47 . 1.377(5) ?
C8 C7 . 1.513(4) ?
C8 C9 . 1.389(4) ?
C8 C13 . 1.363(5) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
C18 C17 . 1.526(4) ?
C24 C26 . 1.517(4) ?
C6 H6A . 1.0000 ?
C6 C7 . 1.537(4) ?
C28 C27 . 1.403(4) ?
C28 C29 . 1.395(5) ?
C28 C33 . 1.517(4) ?
C38 H38 . 1.0000 ?
C38 C37 . 1.537(4) ?
C7 H7A . 0.99(4) ?
C7 H7B . 0.96(3) ?
C40 H40 . 1.0000 ?
C40 C48 . 1.519(4) ?
C40 C41 . 1.525(4) ?
C51 C49 . 1.518(5) ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C49 H49 . 1.0000 ?
C49 C50 . 1.517(5) ?
C31 H31 . 0.9500 ?
C31 C30 . 1.374(5) ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C17 C16 . 1.530(4) ?
C43 H43 . 0.9500 ?
C43 C44 . 1.388(5) ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C35 H35A . 0.9900 ?
C35 H35B . 0.9900 ?
C35 C36 . 1.521(5) ?
C9 H9 . 0.9500 ?
C9 C10 . 1.369(5) ?
C30 H30 . 0.9500 ?
C30 C29 . 1.371(5) ?
C36 H36A . 0.9900 ?
C36 H36B . 0.9900 ?
C36 C37 . 1.526(5) ?
C44 H44 . 0.9500 ?
C44 C45 . 1.371(5) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C29 H29 . 0.9500 ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C50 H50A . 0.9800 ?
C50 H50B . 0.9800 ?
C50 H50C . 0.9800 ?
C13 H13 . 0.9500 ?
C13 C12 . 1.409(5) ?
C3 H3A . 1.0000 ?
C3 H3B . 1.0000 ?
C3 C4A . 1.688(8) ?
C3 C2B . 1.704(13) ?
C3 C4B . 1.389(7) ?
C3 C2A . 1.388(7) ?
C45 H45 . 0.9500 ?
C45 C46 . 1.373(6) ?
C47 H47 . 0.9500 ?
C47 C46 . 1.384(6) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
C11 H11 . 0.9500 ?
C11 C10 . 1.372(6) ?
C11 C12 . 1.363(6) ?
C10 H10 . 0.9500 ?
C12 H12 . 0.9500 ?
C46 H46 . 0.9500 ?
O1B C2B . 1.218(10) ?
C1A H1AA . 0.9800 ?
C1A H1AB . 0.9800 ?
C1A H1AC . 0.9800 ?
C4A H4AA . 1.05(7) ?
C4A H4AB . 0.81(8) ?
C4A H4AC . 1.08(8) ?
C2B O2B . 1.301(17) ?
O11 H11A . 0.8705 ?
O11 H11B . 0.8699 ?
C4B H4BA . 0.9800 ?
C4B H4BB . 0.9800 ?
C4B H4BC . 0.9800 ?
C2A O1A . 1.205(8) ?
O2B C1B . 1.419(13) ?
C1B H1BA . 0.9800 ?
C1B H1BB . 0.9800 ?
C1B H1BC . 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_D
_geom_hbond_site_symmetry_H
_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
N5 H5 O5 1_555 1_555 1_555 0.88 2.07 2.923(3) 162 y
N6 H6 O6 1_555 1_555 1_555 0.88 2.42 3.233(3) 154 y
C9 H9 O2B 1_555 1_555 1_555 0.95 2.35 3.270(18) 164 y
C21 H21 O3 1_555 1_555 1_555 0.95 2.44 3.352(4) 161 y
C35 H35A O5 1_555 1_555 1_555 0.99 2.51 3.171(4) 124 y
C43 H43 O4 1_555 1_555 1_555 0.95 2.59 3.443(4) 149 y
N1 H1 O4 1_555 1_555 4_556 0.88 2.01 2.865(3) 163 y
C1B H1BB O10 1_555 1_555 2_656 0.98 2.46 2.913(16) 108 y
C30 H30 O8 1_555 1_555 1_545 0.95 2.46 3.222(4) 137 y
C35 H35 O7 1_555 1_555 4_545 0.99 2.39 3.228(4) 142 y
C52 H52B O10 1_555 1_555 2_655 0.98 2.60 3.559(5) 166 y
O11 H11A O8 1_555 1_555 1_555 0.87 2.48 3.136(6) 133 y
C13 H13 O11 1_555 1_555 4_546 0.95 2.52 3.155(7) 124 y
C36 H36B Cg3 1_555 1_555 4_546 0.99 2.94 3.845(4) 152 y
C4A H4AC Cg5 1_555 1_555 1_565 1.05(8) 2.93(7) 3.770(8) 135(5) y
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
C20 C19 N3 C15 ? ? ? ? 178.3(2) y
C19 N3 C15 C14 . . . . -73.4(3) y
N3 C15 C14 N2 . . . . -17.5(3) y
C15 C14 N2 C6 . . . . 176.5(2) y
C14 N2 C6 C5 . . . . -163.0(2) y
N2 C6 C5 N1 . . . . 171.4(2) y
C6 C5 N1 C3 . . . . -174.8(3) y
C5 N1 C3 C2B . . . . -58.0(5) y
N1 C3 C2B O2B . . . . -39.6(13) y
C32 C34 N4 C38 . . . . -164.6(2) y
C34 N4 C38 C39 . . . . -69.1(3) y
N4 C38 C39 N5 . . . . -14.4(4) y
C38 C39 N5 C40 . . . . -177.2(2) y
C39 N5 C40 C48 . . . . -106.8(3) y
N5 C40 C48 N6 . . . . 18.6(3) y
C40 C48 N6 C49 . . . . 179.1(2) y
C48 N6 C49 C51 . . . . -60.9(3) y
N6 C49 C51 O9 . . . . -35.0(4) y
