#------------------------------------------------------------------------------
#$Date: 2026-06-05 21:28:25 +0200 (Fri 05 de Jun de 2026) $
#$Revision: 306473 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064366.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_7064366
loop_
_publ_author_name
'Zhu, Xin-Ru'
'Li, Ze'
'Sun, Dan'
'Elmidaoui, Roudaina'
'Dai, Meng-Xuan'
'Zhao, Zhi-Long'
'Chen, Xiang-Zhu'
'Jiang, Fei'
'Liu, Lu'
_publ_section_title
;
 Novel palmatine hydrochloride--phenolic acid cocrystals: effects of
 different phenolic acids on hygroscopicity improvement and antibacterial
 activity enhancement
;
_journal_issue                   18
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7647
_journal_page_last               7657
_journal_paper_doi               10.1039/D5NJ04579G
_journal_volume                  50
_journal_year                    2026
_chemical_formula_sum            'C25 H29 Cl N O7.5'
_chemical_formula_weight         498.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-17 deposited with the CCDC.	2026-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                104.598(2)
_cell_angle_beta                 92.940(2)
_cell_angle_gamma                93.154(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8962(8)
_cell_length_b                   15.0725(11)
_cell_length_c                   15.0474(11)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.13
_cell_measurement_theta_min      2.42
_cell_volume                     2382.4(3)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.1506
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31580
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.067
_diffrn_reflns_theta_max         25.067
_diffrn_reflns_theta_min         2.417
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       Bloc
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0069(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         8343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.2312
_refine_ls_R_factor_gt           0.0888
_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)+(0.0841P)²+2.9520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3417
_reflns_number_total             8343
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5nj04579g2.cif
_cod_data_source_block           z
_cod_depositor_comments
'Adding full bibliography for 7064365--7064366.cif.'
_cod_original_formula_sum        'C25 H29 Cl N O7.50'
_cod_database_code               7064366
_shelx_shelxl_version_number     2018/3
_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'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl -0.01467(15) -0.33233(12) 0.88233(12) 0.0690(6) Uani 1 1 d . . . . .
Cl1 Cl 0.17303(17) 0.60767(15) 0.58700(15) 0.1002(8) Uani 1 1 d . . . . .
O4 O 0.2617(3) 0.5858(2) 0.0618(3) 0.0522(11) Uani 1 1 d . . . . .
O6 O 0.5292(4) -0.0173(3) 0.1030(3) 0.0552(11) Uani 1 1 d . . . . .
O03 O 0.4700(3) 0.6756(3) 0.1046(3) 0.0545(11) Uani 1 1 d . . . . .
O1 O 0.2921(4) 0.7078(3) 0.3619(3) 0.0589(11) Uani 1 1 d . . . . .
O3 O 0.5904(4) 0.1098(3) 0.4068(3) 0.0632(12) Uani 1 1 d . . . . .
O2 O 0.3821(4) 0.0201(3) 0.3780(3) 0.0668(13) Uani 1 1 d . . . . .
O01 O 0.5038(4) 0.8094(3) 0.3650(3) 0.0650(12) Uani 1 1 d . . . . .
N4 N 0.5353(4) 0.2593(3) 0.1132(3) 0.0425(12) Uani 1 1 d . . . . .
O5 O 0.3139(4) -0.1177(3) 0.0934(3) 0.0675(12) Uani 1 1 d . . . . .
O8 O 0.1326(5) -0.2357(3) 0.7622(4) 0.0848(15) Uani 1 1 d G . . . .
HC H 0.088337 -0.272845 0.783305 0.127 Uiso 1 1 d G U . . .
HD H 0.119563 -0.270661 0.708229 0.127 Uiso 1 1 d G U . . .
N2 N 0.2978(4) 0.4372(3) 0.3751(3) 0.0493(13) Uani 1 1 d . . . . .
O7 O 0.0284(4) -0.0708(3) 0.6530(4) 0.0868(16) Uani 1 1 d . . . . .
O05 O 0.0573(4) 0.2712(4) 0.6494(4) 0.0866(16) Uani 1 1 d . . . . .
O06 O 0.1011(5) -0.0619(4) 0.7964(4) 0.1011(18) Uani 1 1 d . . . . .
H06A H 0.107463 -0.117209 0.776188 0.152 Uiso 1 1 calc R U . . .
O09 O 0.1087(4) 0.3609(4) 0.8265(4) 0.1033(19) Uani 1 1 d . . . . .
H09A H 0.072414 0.382150 0.788342 0.155 Uiso 1 1 calc R U . . .
C26 C 0.4421(5) 0.4044(4) 0.1170(4) 0.0406(14) Uani 1 1 d . . . . .
C24 C 0.3527(5) 0.5379(4) 0.0893(4) 0.0409(14) Uani 1 1 d . . . . .
C5 C 0.5186(5) 0.5364(4) 0.3753(4) 0.0430(14) Uani 1 1 d . . . . .
C25 C 0.3391(5) 0.4481(4) 0.0930(3) 0.0399(14) Uani 1 1 d . . . . .
HI H 0.262169 0.416021 0.079669 0.048 Uiso 1 1 calc R U . . .
C35 C 0.4226(5) 0.1195(4) 0.1119(4) 0.0448(15) Uani 1 1 d . . . . .
C12 C 0.3958(5) 0.2961(4) 0.3776(4) 0.0417(14) Uani 1 1 d . . . . .
C33 C 0.3196(5) 0.2581(4) 0.1176(4) 0.0436(15) Uani 1 1 d . . . . .
HJ H 0.247513 0.288739 0.120979 0.052 Uiso 1 1 calc R U . . .
C37 C 0.4199(5) 0.0240(4) 0.1069(4) 0.0455(15) Uani 1 1 d . . . . .
C23 C 0.4685(5) 0.5870(4) 0.1112(4) 0.0435(15) Uani 1 1 d . . . . .
C40 C 0.1995(5) 0.1110(4) 0.1086(4) 0.0539(17) Uani 1 1 d . . . . .
HK H 0.125221 0.138685 0.109903 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4054(5) 0.5774(4) 0.3695(4) 0.0439(15) Uani 1 1 d . . . . .
C27 C 0.5565(5) 0.4536(4) 0.1389(4) 0.0434(15) Uani 1 1 d . . . . .
C34 C 0.3110(5) 0.1643(4) 0.1134(4) 0.0464(15) Uani 1 1 d . . . . .
C10 C 0.4057(5) 0.3934(4) 0.3765(4) 0.0423(14) Uani 1 1 d . . . . .
C36 C 0.5324(5) 0.1707(4) 0.1120(4) 0.0470(15) Uani 1 1 d . . . . .
HL H 0.606110 0.142292 0.111310 0.056 Uiso 1 1 calc R U . . .
C30 C 0.4290(5) 0.3069(4) 0.1168(4) 0.0411(14) Uani 1 1 d . . . . .
C7 C 0.4029(5) 0.6701(4) 0.3648(4) 0.0452(15) Uani 1 1 d . . . . .
C28 C 0.5686(5) 0.5448(4) 0.1365(4) 0.0458(15) Uani 1 1 d . . . . .
HM H 0.644737 0.577724 0.152136 0.055 Uiso 1 1 calc R U . . .
C11 C 0.5142(5) 0.4441(4) 0.3781(3) 0.0450(15) Uani 1 1 d . . . . .
H11 H 0.587828 0.416273 0.381112 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4950(5) 0.1596(4) 0.3909(4) 0.0471(15) Uani 1 1 d . . . . .
C3 C 0.6245(6) 0.6796(4) 0.3734(4) 0.0504(16) Uani 1 1 d . . . . .
H3 H 0.698042 0.714418 0.374928 0.060 Uiso 1 1 calc R U . . .
C2 C 0.5123(6) 0.7204(4) 0.3677(4) 0.0499(16) Uani 1 1 d . . . . .
C13 C 0.2825(5) 0.2451(4) 0.3604(4) 0.0482(15) Uani 1 1 d . . . . .
C16 C 0.5020(5) 0.2513(4) 0.3927(4) 0.0492(16) Uani 1 1 d . . . . .
H16 H 0.578245 0.284349 0.403989 0.059 Uiso 1 1 calc R U . . .
C29 C 0.1436(5) 0.5393(4) 0.0355(4) 0.0597(18) Uani 1 1 d . . . . .
HN H 0.150235 0.485653 -0.013954 0.090 Uiso 1 1 calc R U . . .
HO H 0.089127 0.579481 0.015457 0.090 Uiso 1 1 calc R U . . .
HP H 0.111422 0.521413 0.087055 0.090 Uiso 1 1 calc R U . . .
C9 C 0.2969(5) 0.5240(4) 0.3710(4) 0.0523(16) Uani 1 1 d . . . . .
H9 H 0.221759 0.550181 0.369161 0.063 Uiso 1 1 calc R U . . .
C39 C 0.1994(6) 0.0193(4) 0.1022(4) 0.0550(17) Uani 1 1 d . . . . .
HQ H 0.124375 -0.014586 0.097805 0.066 Uiso 1 1 calc R U . . .
C4 C 0.6282(5) 0.5904(4) 0.3769(4) 0.0494(16) Uani 1 1 d . . . . .
H4 H 0.703725 0.565140 0.380301 0.059 Uiso 1 1 calc R U . . .
C18 C 0.3797(6) 0.1100(4) 0.3755(4) 0.0524(16) Uani 1 1 d . . . . .
C31 C 0.6550(5) 0.3070(4) 0.1027(4) 0.0514(16) Uani 1 1 d . . . . .
HR H 0.661286 0.307335 0.038695 0.062 Uiso 1 1 calc R U . . .
HS H 0.722152 0.274026 0.120338 0.062 Uiso 1 1 calc R U . . .
C38 C 0.3090(6) -0.0260(4) 0.1018(4) 0.0519(16) Uani 1 1 d . . . . .
C19 C 0.2756(6) 0.1531(4) 0.3596(4) 0.0551(17) Uani 1 1 d . . . . .
H19 H 0.199537 0.119819 0.348274 0.066 Uiso 1 1 calc R U . . .
C44 C 0.0688(6) 0.2181(6) 0.7092(6) 0.071(2) Uani 1 1 d . . . . .
C32 C 0.6656(5) 0.4042(4) 0.1615(4) 0.0517(16) Uani 1 1 d . . . . .
HT H 0.668606 0.404163 0.226045 0.062 Uiso 1 1 calc R U . . .
HU H 0.741105 0.435752 0.150399 0.062 Uiso 1 1 calc R U . . .
C14 C 0.1702(6) 0.2922(5) 0.3407(5) 0.0674(19) Uani 1 1 d . . . . .
H14A H 0.159182 0.286045 0.274989 0.081 Uiso 1 1 calc R U . . .
H14B H 0.098295 0.262198 0.359078 0.081 Uiso 1 1 calc R U . . .
C50 C 0.0655(6) -0.0261(6) 0.7285(7) 0.076(2) Uani 1 1 d . . . . .
C15 C 0.1791(5) 0.3895(4) 0.3890(5) 0.069(2) Uani 1 1 d . . . . .
H15A H 0.172323 0.395576 0.454240 0.083 Uiso 1 1 calc R U . . .
H15B H 0.111022 0.418862 0.367017 0.083 Uiso 1 1 calc R U . . .
C48 C 0.0770(6) 0.0767(5) 0.7564(6) 0.071(2) Uani 1 1 d . . . . .
C20 C 0.7098(5) 0.1549(4) 0.4200(5) 0.0681(19) Uani 1 1 d . . . . .
H20A H 0.727772 0.175780 0.366474 0.102 Uiso 1 1 calc R U . . .
H20B H 0.769242 0.112952 0.429540 0.102 Uiso 1 1 calc R U . . .
H20C H 0.713450 0.206609 0.472771 0.102 Uiso 1 1 calc R U . . .
C01 C 0.6108(6) 0.8712(4) 0.3844(4) 0.0663(19) Uani 1 1 d . . . . .
H01A H 0.589202 0.930791 0.379579 0.099 Uiso 1 1 calc R U . . .
H01B H 0.644597 0.875499 0.445618 0.099 Uiso 1 1 calc R U . . .
H01C H 0.670740 0.849019 0.341063 0.099 Uiso 1 1 calc R U . . .
C42 C 0.2009(6) -0.1719(4) 0.0896(5) 0.073(2) Uani 1 1 d . . . . .
HV H 0.151094 -0.170828 0.035450 0.109 Uiso 1 1 calc R U . . .
HW H 0.157479 -0.147183 0.143255 0.109 Uiso 1 1 calc R U . . .
HX H 0.218417 -0.234080 0.087594 0.109 Uiso 1 1 calc R U . . .
C45 C 0.0945(6) 0.2676(6) 0.8000(6) 0.079(2) Uani 1 1 d . . . . .
C46 C 0.1095(6) 0.2218(7) 0.8687(6) 0.085(3) Uani 1 1 d . . . . .
HY H 0.123237 0.255241 0.929763 0.102 Uiso 1 1 calc R U . . .
C22 C 0.5848(6) 0.7270(4) 0.1205(4) 0.068(2) Uani 1 1 d . . . . .
HZ H 0.643398 0.693715 0.082001 0.102 Uiso 1 1 calc R U . . .
H1 H 0.613371 0.737143 0.183946 0.102 Uiso 1 1 calc R U . . .
H2 H 0.575822 0.785072 0.106443 0.102 Uiso 1 1 calc R U . . .
C49 C 0.0583(6) 0.1232(6) 0.6888(5) 0.073(2) Uani 1 1 d . . . . .
H5 H 0.038288 0.089782 0.628334 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2475(6) 0.7108(5) 0.2726(5) 0.081(2) Uani 1 1 d . . . . .
H8A H 0.224403 0.649532 0.236220 0.121 Uiso 1 1 calc R U . . .
H8B H 0.310831 0.738170 0.243912 0.121 Uiso 1 1 calc R U . . .
H8C H 0.176992 0.746819 0.277202 0.121 Uiso 1 1 calc R U . . .
C47 C 0.1040(6) 0.1250(6) 0.8468(5) 0.080(2) Uani 1 1 d . . . . .
H6 H 0.118251 0.094359 0.892346 0.096 Uiso 1 1 calc R U . . .
C41 C 0.5776(6) -0.0238(5) 0.1903(5) 0.080(2) Uani 1 1 d . . . . .
H7 H 0.653519 -0.053520 0.183403 0.120 Uiso 1 1 calc R U . . .
H8 H 0.519560 -0.058975 0.215949 0.120 Uiso 1 1 calc R U . . .
H10 H 0.592558 0.036736 0.230643 0.120 Uiso 1 1 calc R U . . .
C21 C 0.2666(7) -0.0323(5) 0.3701(5) 0.087(2) Uani 1 1 d . . . . .
H21A H 0.226101 -0.037581 0.310644 0.131 Uiso 1 1 calc R U . . .
H21B H 0.215623 -0.001916 0.417057 0.131 Uiso 1 1 calc R U . . .
H21C H 0.280499 -0.092475 0.377423 0.131 Uiso 1 1 calc R U . . .
C43 C 0.0136(7) 0.2262(6) 0.5571(6) 0.105(3) Uani 1 1 d . . . . .
H12 H 0.003380 0.271163 0.522570 0.158 Uiso 1 1 calc R U . . .
H13 H -0.064088 0.193004 0.557370 0.158 Uiso 1 1 calc R U . . .
H14 H 0.072130 0.184163 0.529248 0.158 Uiso 1 1 calc R U . . .
O07 O 0.0199(6) 0.4785(4) 0.7377(4) 0.150(3) Uani 1 1 d . . . . .
H07A H 0.067358 0.526054 0.741163 0.225 Uiso 1 1 d R U . . .
H07B H -0.042872 0.496554 0.766663 0.225 Uiso 1 1 d R U . . .
O08 O 0.0269(11) 0.4433(7) 0.5722(8) 0.287(6) Uani 1 1 d . . . . .
H08A H 0.017382 0.412537 0.611870 0.431 Uiso 1 1 d R U . . .
H08B H 0.048032 0.499647 0.596760 0.431 Uiso 1 1 d R U . . .
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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 O4 C29 117.6(4) . . ?
C37 O6 C41 113.1(4) . . ?
C23 O03 C22 117.3(5) . . ?
C7 O1 C8 114.4(4) . . ?
C17 O3 C20 117.0(5) . . ?
C18 O2 C21 117.7(5) . . ?
C2 O01 C01 119.8(5) . . ?
C36 N4 C30 122.2(5) . . ?
C36 N4 C31 118.7(5) . . ?
C30 N4 C31 118.9(5) . . ?
C38 O5 C42 118.5(5) . . ?
HC O8 HD 90.2 . . ?
C9 N2 C10 122.2(5) . . ?
C9 N2 C15 118.1(5) . . ?
C10 N2 C15 119.4(5) . . ?
C44 O05 C43 117.1(6) . . ?
C50 O06 H06A 109.5 . . ?
C45 O09 H09A 109.5 . . ?
C27 C26 C25 119.8(5) . . ?
C27 C26 C30 120.4(5) . . ?
C25 C26 C30 119.8(5) . . ?
O4 C24 C25 125.0(5) . . ?
O4 C24 C23 114.7(5) . . ?
C25 C24 C23 120.2(5) . . ?
C11 C5 C4 124.0(5) . . ?
C11 C5 C6 118.0(5) . . ?
C4 C5 C6 118.0(5) . . ?
C24 C25 C26 119.7(5) . . ?
C24 C25 HI 120.2 . . ?
C26 C25 HI 120.2 . . ?
C36 C35 C37 121.5(5) . . ?
C36 C35 C34 118.2(6) . . ?
C37 C35 C34 120.3(5) . . ?
C13 C12 C16 118.4(5) . . ?
C13 C12 C10 121.2(5) . . ?
C16 C12 C10 120.3(5) . . ?
C30 C33 C34 123.0(5) . . ?
C30 C33 HJ 118.5 . . ?
C34 C33 HJ 118.5 . . ?
O6 C37 C38 121.3(5) . . ?
O6 C37 C35 118.6(5) . . ?
C38 C37 C35 120.1(5) . . ?
O03 C23 C28 125.4(5) . . ?
O03 C23 C24 114.6(5) . . ?
C28 C23 C24 120.0(5) . . ?
C39 C40 C34 120.6(6) . . ?
C39 C40 HK 119.7 . . ?
C34 C40 HK 119.7 . . ?
C9 C6 C5 117.6(5) . . ?
C9 C6 C7 121.3(5) . . ?
C5 C6 C7 121.0(5) . . ?
C28 C27 C26 120.0(5) . . ?
C28 C27 C32 121.4(5) . . ?
C26 C27 C32 118.5(5) . . ?
C33 C34 C40 124.4(5) . . ?
C33 C34 C35 117.6(5) . . ?
C40 C34 C35 118.0(6) . . ?
C11 C10 N2 117.6(5) . . ?
C11 C10 C12 124.7(5) . . ?
N2 C10 C12 117.7(5) . . ?
N4 C36 C35 121.9(5) . . ?
N4 C36 HL 119.1 . . ?
C35 C36 HL 119.1 . . ?
C33 C30 N4 117.1(5) . . ?
C33 C30 C26 125.0(5) . . ?
N4 C30 C26 117.9(5) . . ?
O1 C7 C2 121.9(5) . . ?
O1 C7 C6 119.2(5) . . ?
C2 C7 C6 118.8(5) . . ?
C23 C28 C27 120.3(5) . . ?
C23 C28 HM 119.9 . . ?
C27 C28 HM 119.9 . . ?
C10 C11 C5 122.5(5) . . ?
C10 C11 H11 118.7 . . ?
C5 C11 H11 118.7 . . ?
O3 C17 C16 126.4(5) . . ?
O3 C17 C18 114.1(6) . . ?
C16 C17 C18 119.5(6) . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
O01 C2 C7 116.0(5) . . ?
O01 C2 C3 124.0(6) . . ?
C7 C2 C3 120.0(6) . . ?
C19 C13 C12 120.2(5) . . ?
C19 C13 C14 121.5(6) . . ?
C12 C13 C14 118.3(6) . . ?
C17 C16 C12 121.2(5) . . ?
C17 C16 H16 119.4 . . ?
C12 C16 H16 119.4 . . ?
O4 C29 HN 109.5 . . ?
O4 C29 HO 109.5 . . ?
HN C29 HO 109.5 . . ?
O4 C29 HP 109.5 . . ?
HN C29 HP 109.5 . . ?
HO C29 HP 109.5 . . ?
N2 C9 C6 122.0(5) . . ?
N2 C9 H9 119.0 . . ?
C6 C9 H9 119.0 . . ?
C40 C39 C38 122.2(6) . . ?
C40 C39 HQ 118.9 . . ?
C38 C39 HQ 118.9 . . ?
C3 C4 C5 120.3(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O2 C18 C19 125.4(6) . . ?
O2 C18 C17 115.0(6) . . ?
C19 C18 C17 119.6(6) . . ?
N4 C31 C32 110.8(5) . . ?
N4 C31 HR 109.5 . . ?
C32 C31 HR 109.5 . . ?
N4 C31 HS 109.5 . . ?
C32 C31 HS 109.5 . . ?
HR C31 HS 108.1 . . ?
O5 C38 C37 116.6(6) . . ?
O5 C38 C39 124.5(6) . . ?
C37 C38 C39 118.8(6) . . ?
C18 C19 C13 121.0(6) . . ?
C18 C19 H19 119.5 . . ?
C13 C19 H19 119.5 . . ?
O05 C44 C49 127.2(7) . . ?
O05 C44 C45 113.8(8) . . ?
C49 C44 C45 119.0(9) . . ?
C27 C32 C31 109.5(5) . . ?
C27 C32 HT 109.8 . . ?
C31 C32 HT 109.8 . . ?
C27 C32 HU 109.8 . . ?
C31 C32 HU 109.8 . . ?
HT C32 HU 108.2 . . ?
C15 C14 C13 112.2(5) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
O7 C50 O06 124.0(8) . . ?
O7 C50 C48 123.9(8) . . ?
O06 C50 C48 112.1(8) . . ?
C14 C15 N2 112.1(5) . . ?
C14 C15 H15A 109.2 . . ?
N2 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
N2 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C47 C48 C49 120.2(7) . . ?
C47 C48 C50 121.7(9) . . ?
C49 C48 C50 118.2(7) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O01 C01 H01A 109.5 . . ?
O01 C01 H01B 109.5 . . ?
H01A C01 H01B 109.5 . . ?
O01 C01 H01C 109.5 . . ?
H01A C01 H01C 109.5 . . ?
H01B C01 H01C 109.5 . . ?
O5 C42 HV 109.5 . . ?
O5 C42 HW 109.5 . . ?
HV C42 HW 109.5 . . ?
O5 C42 HX 109.5 . . ?
HV C42 HX 109.5 . . ?
HW C42 HX 109.5 . . ?
O09 C45 C46 116.7(8) . . ?
O09 C45 C44 123.3(9) . . ?
C46 C45 C44 120.0(8) . . ?
C45 C46 C47 120.6(7) . . ?
C45 C46 HY 119.7 . . ?
C47 C46 HY 119.7 . . ?
O03 C22 HZ 109.5 . . ?
O03 C22 H1 109.5 . . ?
HZ C22 H1 109.5 . . ?
O03 C22 H2 109.5 . . ?
HZ C22 H2 109.5 . . ?
H1 C22 H2 109.5 . . ?
C44 C49 C48 121.4(7) . . ?
C44 C49 H5 119.3 . . ?
C48 C49 H5 119.3 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C48 C47 C46 118.7(8) . . ?
C48 C47 H6 120.7 . . ?
C46 C47 H6 120.7 . . ?
O6 C41 H7 109.5 . . ?
O6 C41 H8 109.5 . . ?
H7 C41 H8 109.5 . . ?
O6 C41 H10 109.5 . . ?
H7 C41 H10 109.5 . . ?
H8 C41 H10 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O05 C43 H12 109.5 . . ?
O05 C43 H13 109.5 . . ?
H12 C43 H13 109.5 . . ?
O05 C43 H14 109.5 . . ?
H12 C43 H14 109.5 . . ?
H13 C43 H14 109.5 . . ?
H07A O07 H07B 106.8 . . ?
H08A O08 H08B 112.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C24 1.365(6) . ?
O4 C29 1.419(6) . ?
O6 C37 1.370(6) . ?
O6 C41 1.420(7) . ?
O03 C23 1.363(6) . ?
O03 C22 1.411(6) . ?
O1 C7 1.365(6) . ?
O1 C8 1.418(7) . ?
O3 C17 1.361(6) . ?
O3 C20 1.416(7) . ?
O2 C18 1.367(7) . ?
O2 C21 1.432(7) . ?
O01 C2 1.361(7) . ?
O01 C01 1.421(7) . ?
N4 C36 1.329(6) . ?
N4 C30 1.392(6) . ?
N4 C31 1.489(6) . ?
O5 C38 1.359(7) . ?
O5 C42 1.430(7) . ?
O8 HC 0.8500 . ?
O8 HD 0.8500 . ?
N2 C9 1.326(7) . ?
N2 C10 1.382(7) . ?
N2 C15 1.495(7) . ?
O7 C50 1.202(8) . ?
O05 C44 1.352(9) . ?
O05 C43 1.427(8) . ?
O06 C50 1.322(9) . ?
O06 H06A 0.8200 . ?
O09 C45 1.359(9) . ?
O09 H09A 0.8200 . ?
C26 C27 1.394(7) . ?
C26 C25 1.408(7) . ?
C26 C30 1.469(7) . ?
C24 C25 1.369(7) . ?
C24 C23 1.407(7) . ?
C5 C11 1.400(7) . ?
C5 C4 1.404(7) . ?
C5 C6 1.418(7) . ?
C25 HI 0.9300 . ?
C35 C36 1.388(7) . ?
C35 C37 1.421(8) . ?
C35 C34 1.421(7) . ?
C12 C13 1.394(7) . ?
C12 C16 1.408(7) . ?
C12 C10 1.469(7) . ?
C33 C30 1.369(7) . ?
C33 C34 1.397(7) . ?
C33 HJ 0.9300 . ?
C37 C38 1.377(8) . ?
C23 C28 1.378(7) . ?
C40 C39 1.360(7) . ?
C40 C34 1.408(7) . ?
C40 HK 0.9300 . ?
C6 C9 1.398(8) . ?
C6 C7 1.418(7) . ?
C27 C28 1.383(7) . ?
C27 C32 1.506(7) . ?
C10 C11 1.368(7) . ?
C36 HL 0.9300 . ?
C7 C2 1.371(8) . ?
C28 HM 0.9300 . ?
C11 H11 0.9300 . ?
C17 C16 1.372(7) . ?
C17 C18 1.403(8) . ?
C3 C4 1.360(7) . ?
C3 C2 1.407(8) . ?
C3 H3 0.9300 . ?
C13 C19 1.381(8) . ?
C13 C14 1.502(8) . ?
C16 H16 0.9300 . ?
C29 HN 0.9600 . ?
C29 HO 0.9600 . ?
C29 HP 0.9600 . ?
C9 H9 0.9300 . ?
C39 C38 1.408(8) . ?
C39 HQ 0.9300 . ?
C4 H4 0.9300 . ?
C18 C19 1.378(8) . ?
C31 C32 1.504(7) . ?
C31 HR 0.9700 . ?
C31 HS 0.9700 . ?
C19 H19 0.9300 . ?
C44 C49 1.382(10) . ?
C44 C45 1.388(10) . ?
C32 HT 0.9700 . ?
C32 HU 0.9700 . ?
C14 C15 1.458(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C50 C48 1.496(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C48 C47 1.379(9) . ?
C48 C49 1.386(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C01 H01A 0.9600 . ?
C01 H01B 0.9600 . ?
C01 H01C 0.9600 . ?
C42 HV 0.9600 . ?
C42 HW 0.9600 . ?
C42 HX 0.9600 . ?
C45 C46 1.389(10) . ?
C46 C47 1.408(10) . ?
C46 HY 0.9300 . ?
C22 HZ 0.9600 . ?
C22 H1 0.9600 . ?
C22 H2 0.9600 . ?
C49 H5 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C47 H6 0.9300 . ?
C41 H7 0.9600 . ?
C41 H8 0.9600 . ?
C41 H10 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C43 H12 0.9600 . ?
C43 H13 0.9600 . ?
C43 H14 0.9600 . ?
O07 H07A 0.8500 . ?
O07 H07B 0.8500 . ?
O08 H08A 0.8500 . ?
O08 H08B 0.8501 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C29 O4 C24 C25 0.3(8) . . . . ?
C29 O4 C24 C23 177.8(5) . . . . ?
O4 C24 C25 C26 176.0(5) . . . . ?
C23 C24 C25 C26 -1.3(8) . . . . ?
C27 C26 C25 C24 1.5(8) . . . . ?
C30 C26 C25 C24 -177.1(5) . . . . ?
C41 O6 C37 C38 -87.0(7) . . . . ?
C41 O6 C37 C35 95.9(6) . . . . ?
C36 C35 C37 O6 0.6(8) . . . . ?
C34 C35 C37 O6 178.3(5) . . . . ?
C36 C35 C37 C38 -176.5(5) . . . . ?
C34 C35 C37 C38 1.2(8) . . . . ?
C22 O03 C23 C28 3.4(8) . . . . ?
C22 O03 C23 C24 -176.4(5) . . . . ?
O4 C24 C23 O03 2.2(7) . . . . ?
C25 C24 C23 O03 179.8(5) . . . . ?
O4 C24 C23 C28 -177.6(5) . . . . ?
C25 C24 C23 C28 0.0(8) . . . . ?
C11 C5 C6 C9 2.8(8) . . . . ?
C4 C5 C6 C9 -177.9(5) . . . . ?
C11 C5 C6 C7 -178.9(5) . . . . ?
C4 C5 C6 C7 0.4(8) . . . . ?
C25 C26 C27 C28 -0.3(8) . . . . ?
C30 C26 C27 C28 178.3(5) . . . . ?
C25 C26 C27 C32 -178.2(5) . . . . ?
C30 C26 C27 C32 0.4(8) . . . . ?
C30 C33 C34 C40 -176.1(5) . . . . ?
C30 C33 C34 C35 2.4(8) . . . . ?
C39 C40 C34 C33 178.1(6) . . . . ?
C39 C40 C34 C35 -0.4(8) . . . . ?
C36 C35 C34 C33 -1.7(8) . . . . ?
C37 C35 C34 C33 -179.4(5) . . . . ?
C36 C35 C34 C40 176.9(5) . . . . ?
C37 C35 C34 C40 -0.9(8) . . . . ?
C9 N2 C10 C11 3.2(8) . . . . ?
C15 N2 C10 C11 -170.0(5) . . . . ?
C9 N2 C10 C12 -177.8(5) . . . . ?
C15 N2 C10 C12 9.1(7) . . . . ?
C13 C12 C10 C11 -169.1(5) . . . . ?
C16 C12 C10 C11 8.4(8) . . . . ?
C13 C12 C10 N2 11.9(8) . . . . ?
C16 C12 C10 N2 -170.6(5) . . . . ?
C30 N4 C36 C35 1.8(8) . . . . ?
C31 N4 C36 C35 -173.3(5) . . . . ?
C37 C35 C36 N4 177.4(5) . . . . ?
C34 C35 C36 N4 -0.3(8) . . . . ?
C34 C33 C30 N4 -1.0(8) . . . . ?
C34 C33 C30 C26 177.2(5) . . . . ?
C36 N4 C30 C33 -1.2(7) . . . . ?
C31 N4 C30 C33 173.9(5) . . . . ?
C36 N4 C30 C26 -179.5(5) . . . . ?
C31 N4 C30 C26 -4.4(7) . . . . ?
C27 C26 C30 C33 164.1(5) . . . . ?
C25 C26 C30 C33 -17.3(8) . . . . ?
C27 C26 C30 N4 -17.7(7) . . . . ?
C25 C26 C30 N4 160.9(5) . . . . ?
C8 O1 C7 C2 83.2(7) . . . . ?
C8 O1 C7 C6 -99.9(6) . . . . ?
C9 C6 C7 O1 0.1(8) . . . . ?
C5 C6 C7 O1 -178.2(5) . . . . ?
C9 C6 C7 C2 177.1(5) . . . . ?
C5 C6 C7 C2 -1.2(8) . . . . ?
O03 C23 C28 C27 -178.6(5) . . . . ?
C24 C23 C28 C27 1.2(8) . . . . ?
C26 C27 C28 C23 -1.0(8) . . . . ?
C32 C27 C28 C23 176.8(5) . . . . ?
N2 C10 C11 C5 -2.1(8) . . . . ?
C12 C10 C11 C5 178.8(5) . . . . ?
C4 C5 C11 C10 179.9(5) . . . . ?
C6 C5 C11 C10 -0.8(8) . . . . ?
C20 O3 C17 C16 -4.8(8) . . . . ?
C20 O3 C17 C18 178.1(5) . . . . ?
C01 O01 C2 C7 168.5(5) . . . . ?
C01 O01 C2 C3 -11.2(8) . . . . ?
O1 C7 C2 O01 -1.7(8) . . . . ?
C6 C7 C2 O01 -178.6(5) . . . . ?
O1 C7 C2 C3 178.1(5) . . . . ?
C6 C7 C2 C3 1.1(8) . . . . ?
C4 C3 C2 O01 179.3(5) . . . . ?
C4 C3 C2 C7 -0.4(9) . . . . ?
C16 C12 C13 C19 1.0(8) . . . . ?
C10 C12 C13 C19 178.5(5) . . . . ?
C16 C12 C13 C14 -177.6(5) . . . . ?
C10 C12 C13 C14 -0.1(8) . . . . ?
O3 C17 C16 C12 -178.1(5) . . . . ?
C18 C17 C16 C12 -1.2(8) . . . . ?
C13 C12 C16 C17 -0.3(8) . . . . ?
C10 C12 C16 C17 -177.8(5) . . . . ?
C10 N2 C9 C6 -1.1(8) . . . . ?
C15 N2 C9 C6 172.1(5) . . . . ?
C5 C6 C9 N2 -1.9(8) . . . . ?
C7 C6 C9 N2 179.8(5) . . . . ?
C34 C40 C39 C38 1.3(9) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
C11 C5 C4 C3 179.7(5) . . . . ?
C6 C5 C4 C3 0.3(8) . . . . ?
C21 O2 C18 C19 -4.8(9) . . . . ?
C21 O2 C18 C17 175.1(5) . . . . ?
O3 C17 C18 O2 -0.7(7) . . . . ?
C16 C17 C18 O2 -178.0(5) . . . . ?
O3 C17 C18 C19 179.3(5) . . . . ?
C16 C17 C18 C19 1.9(9) . . . . ?
C36 N4 C31 C32 -143.5(5) . . . . ?
C30 N4 C31 C32 41.3(6) . . . . ?
C42 O5 C38 C37 178.9(5) . . . . ?
C42 O5 C38 C39 -3.6(9) . . . . ?
O6 C37 C38 O5 0.4(8) . . . . ?
C35 C37 C38 O5 177.4(5) . . . . ?
O6 C37 C38 C39 -177.3(5) . . . . ?
C35 C37 C38 C39 -0.3(8) . . . . ?
C40 C39 C38 O5 -178.4(6) . . . . ?
C40 C39 C38 C37 -1.0(9) . . . . ?
O2 C18 C19 C13 178.7(5) . . . . ?
C17 C18 C19 C13 -1.3(9) . . . . ?
C12 C13 C19 C18 -0.2(9) . . . . ?
C14 C13 C19 C18 178.4(6) . . . . ?
C43 O05 C44 C49 9.1(10) . . . . ?
C43 O05 C44 C45 -171.3(6) . . . . ?
C28 C27 C32 C31 -141.9(5) . . . . ?
C26 C27 C32 C31 35.9(7) . . . . ?
N4 C31 C32 C27 -55.1(6) . . . . ?
C19 C13 C14 C15 149.9(6) . . . . ?
C12 C13 C14 C15 -31.5(8) . . . . ?
C13 C14 C15 N2 50.1(8) . . . . ?
C9 N2 C15 C14 145.8(6) . . . . ?
C10 N2 C15 C14 -40.7(8) . . . . ?
O7 C50 C48 C47 171.1(7) . . . . ?
O06 C50 C48 C47 -9.1(9) . . . . ?
O7 C50 C48 C49 -8.2(10) . . . . ?
O06 C50 C48 C49 171.7(6) . . . . ?
O05 C44 C45 O09 -0.9(9) . . . . ?
C49 C44 C45 O09 178.8(6) . . . . ?
O05 C44 C45 C46 -179.6(6) . . . . ?
C49 C44 C45 C46 0.1(10) . . . . ?
O09 C45 C46 C47 -176.1(6) . . . . ?
C44 C45 C46 C47 2.7(10) . . . . ?
O05 C44 C49 C48 177.4(6) . . . . ?
C45 C44 C49 C48 -2.2(10) . . . . ?
C47 C48 C49 C44 1.5(10) . . . . ?
C50 C48 C49 C44 -179.3(6) . . . . ?
C49 C48 C47 C46 1.3(9) . . . . ?
C50 C48 C47 C46 -177.9(6) . . . . ?
C45 C46 C47 C48 -3.4(10) . . . . ?
