#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:53:12 +0100 (Sat 06 de Nov de 2021) $
#$Revision: 270434 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/34/7243431.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_7243431
loop_
_publ_author_name
'Jiang, Qi'
'Hirsh, David A.'
'Tu, Yifan'
'Luo, Laibin'
_publ_section_title
;
 Multicomponent crystals of an artemisinin derivative and cinchona
 alkaloids for use as antimalarial drugs
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6843
_journal_page_last               6847
_journal_paper_doi               10.1039/D1CE00974E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'Cl, C20 H25 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C20 H29 Cl N2 O4'
_chemical_formula_weight         396.90
_chemical_name_systematic        'QN HCl 2H2O'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-15 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                98.689(2)
_cell_angle_beta                 97.586(2)
_cell_angle_gamma                108.323(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7848(3)
_cell_length_b                   10.6171(5)
_cell_length_c                   15.4805(8)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.245
_cell_measurement_theta_min      2.942
_cell_volume                     1027.12(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28580
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.245
_diffrn_reflns_theta_max         67.245
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.65
_diffrn_source_power             0.02925
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    1.873
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.4263
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation in aqueous solution'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_coef       0.015(5)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0804
_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)+(0.1935P)²+0.2661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2213
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.923
_reflns_Friedel_fraction_max     0.923
_reflns_number_gt                6911
_reflns_number_total             6948
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00974e2.cif
_cod_data_source_block           scx21_011
_cod_depositor_comments
'Adding full bibliography for 7243430--7243431.cif.'
_cod_database_code               7243431
_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.
;
_shelx_estimated_absorpt_t_max   0.835
_shelx_estimated_absorpt_t_min   0.603
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O6(H6A), O7(H7A,H7B), O8(H8A)
2.b Ternary CH refined with riding coordinates:
 N4(H4A), N2(H2A), C31(H31), C11(H11), C18(H18), C12(H12), C34(H34), C38(H38),
 C32(H32), C14(H14)
2.c Secondary CH2 refined with riding coordinates:
 C36(H36A,H36B), C33(H33A,H33B), C16(H16A,H16B), C35(H35A,H35B), C37(H37A,
 H37B), C13(H13A,H13B), C17(H17A,H17B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C24(H24), C28(H28), C4(H4B), C8(H8), C29(H29), C27(H27), C7(H7),
 C23(H23), C3(H3), C39(H39), C19(H19)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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
Cl1 Cl 0.15060(19) 0.74680(12) 0.47247(9) 0.0234(4) Uani 1 1 d . . . . .
Cl2 Cl 0.6507(2) 0.25762(13) 0.53565(10) 0.0262(4) Uani 1 1 d . . . . .
O4 O 0.0231(6) 0.5570(4) 0.2850(3) 0.0184(8) Uani 1 1 d . . . . .
H4 H 0.030742 0.612539 0.331238 0.028 Uiso 1 1 calc R U . . .
O2 O -0.6923(6) 0.4607(4) -0.2843(3) 0.0207(9) Uani 1 1 d . . . . .
H2 H -0.752039 0.416744 -0.336012 0.031 Uiso 1 1 calc R U . . .
O3 O 0.9407(7) 0.8835(4) 0.1763(3) 0.0225(9) Uani 1 1 d . . . . .
O1 O -0.0424(7) 0.1277(4) -0.1754(3) 0.0225(9) Uani 1 1 d . . . . .
O6 O 0.1234(8) 0.2836(5) 0.5628(3) 0.0270(10) Uani 1 1 d G . . . .
H6A H 0.131127 0.206266 0.566777 0.041 Uiso 1 1 d G U . . .
O5 O 0.6871(8) 0.7255(5) 0.4116(3) 0.0263(10) Uani 1 1 d . . . . .
O7 O 0.5505(8) 0.9453(5) 0.4187(4) 0.0347(12) Uani 1 1 d G . . . .
H7A H 0.617974 0.943051 0.468511 0.052 Uiso 1 1 d G U . . .
H7B H 0.421739 0.903413 0.419670 0.052 Uiso 1 1 d G U . . .
N4 N 0.4096(7) 0.4700(5) 0.3388(3) 0.0170(10) Uani 1 1 d . . . . .
H4A H 0.506978 0.561512 0.372011 0.020 Uiso 1 1 calc R U . . .
N3 N 0.1198(8) 0.6738(5) -0.0137(3) 0.0221(11) Uani 1 1 d . . . . .
O8 O 0.2371(10) 1.0556(5) 0.5781(4) 0.0420(13) Uani 1 1 d G . . . .
H8A H 0.217667 0.978227 0.546770 0.063 Uiso 1 1 d G U . . .
N2 N -0.2578(8) 0.5389(5) -0.3416(3) 0.0194(10) Uani 1 1 d . . . . .
H2A H -0.274626 0.445782 -0.373283 0.023 Uiso 1 1 calc R U . . .
N1 N -0.5386(8) 0.3410(5) 0.0142(3) 0.0220(10) Uani 1 1 d . . . . .
C25 C 0.3187(10) 0.7207(5) 0.0380(4) 0.0185(11) Uani 1 1 d . . . . .
C5 C -0.4166(9) 0.2948(5) -0.0372(4) 0.0193(12) Uani 1 1 d . . . . .
C36 C 0.2503(9) 0.4124(6) 0.3957(4) 0.0185(12) Uani 1 1 d . . . . .
H36A H 0.181187 0.478556 0.414655 0.022 Uiso 1 1 calc R U . . .
H36B H 0.323267 0.394254 0.449719 0.022 Uiso 1 1 calc R U . . .
C30 C 0.1859(9) 0.6297(5) 0.1620(4) 0.0157(11) Uani 1 1 d . . . . .
C9 C -0.6496(9) 0.4336(5) -0.1095(4) 0.0188(11) Uani 1 1 d . . . . .
H9 H -0.732567 0.483216 -0.131653 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4902(10) 0.7869(6) -0.0014(4) 0.0230(12) Uani 1 1 d . . . . .
H24 H 0.463648 0.797046 -0.061350 0.028 Uiso 1 1 calc R U . . .
C10 C -0.5281(9) 0.3880(5) -0.1615(4) 0.0176(11) Uani 1 1 d . . . . .
C28 C -0.0360(10) 0.6103(6) 0.0228(4) 0.0215(12) Uani 1 1 d . . . . .
H28 H -0.175077 0.578949 -0.011716 0.026 Uiso 1 1 calc R U . . .
C4 C -0.2908(9) 0.2246(6) 0.0014(4) 0.0211(12) Uani 1 1 d . . . . .
H4B H -0.294445 0.211879 0.060663 0.025 Uiso 1 1 calc R U . . .
C8 C -0.6518(10) 0.4072(6) -0.0229(4) 0.0226(12) Uani 1 1 d . . . . .
H8 H -0.740028 0.438823 0.010915 0.027 Uiso 1 1 calc R U . . .
C29 C -0.0112(9) 0.5854(5) 0.1098(4) 0.0191(12) Uani 1 1 d . . . . .
H29 H -0.131130 0.538089 0.132053 0.023 Uiso 1 1 calc R U . . .
C26 C 0.3613(9) 0.7032(5) 0.1268(4) 0.0164(11) Uani 1 1 d . . . . .
C33 C 0.1600(9) 0.3435(5) 0.1979(4) 0.0184(11) Uani 1 1 d . . . . .
H33A H 0.203656 0.316723 0.141414 0.022 Uiso 1 1 calc R U . . .
H33B H 0.015750 0.347309 0.183559 0.022 Uiso 1 1 calc R U . . .
C31 C 0.2181(9) 0.5972(5) 0.2542(3) 0.0157(11) Uani 1 1 d . . . . .
H31 H 0.319932 0.679518 0.296605 0.019 Uiso 1 1 calc R U . . .
C16 C -0.3950(10) 0.5952(6) -0.3984(4) 0.0242(13) Uani 1 1 d . . . . .
H16A H -0.543260 0.532541 -0.412075 0.029 Uiso 1 1 calc R U . . .
H16B H -0.345567 0.604148 -0.455281 0.029 Uiso 1 1 calc R U . . .
C11 C -0.5200(9) 0.4193(5) -0.2543(4) 0.0167(11) Uani 1 1 d . . . . .
H11 H -0.527539 0.336038 -0.296526 0.020 Uiso 1 1 calc R U . . .
C35 C 0.0838(9) 0.2804(6) 0.3409(4) 0.0202(12) Uani 1 1 d . . . . .
H35A H 0.063135 0.208373 0.376065 0.024 Uiso 1 1 calc R U . . .
H35B H -0.053085 0.294376 0.325407 0.024 Uiso 1 1 calc R U . . .
C6 C -0.4072(9) 0.3129(5) -0.1265(4) 0.0174(11) Uani 1 1 d . . . . .
C18 C -0.0045(9) 0.7753(6) -0.2872(4) 0.0205(12) Uani 1 1 d . . . . .
H18 H 0.027356 0.833010 -0.332540 0.025 Uiso 1 1 calc R U . . .
C2 C -0.1635(10) 0.1883(5) -0.1352(4) 0.0200(12) Uani 1 1 d . . . . .
C12 C -0.3082(9) 0.5313(5) -0.2494(3) 0.0170(11) Uani 1 1 d . . . . .
H12 H -0.195479 0.506359 -0.215080 0.020 Uiso 1 1 calc R U . . .
C34 C 0.1595(9) 0.2382(5) 0.2561(4) 0.0190(11) Uani 1 1 d . . . . .
H34 H 0.061091 0.146775 0.223270 0.023 Uiso 1 1 calc R U . . .
C38 C 0.3847(9) 0.2329(5) 0.2819(4) 0.0190(12) Uani 1 1 d . . . . .
H38 H 0.381784 0.175263 0.327533 0.023 Uiso 1 1 calc R U . . .
C27 C 0.5728(10) 0.7567(5) 0.1760(4) 0.0183(11) Uani 1 1 d . . . . .
H27 H 0.602478 0.746523 0.235747 0.022 Uiso 1 1 calc R U . . .
C22 C 0.7348(10) 0.8235(5) 0.1361(4) 0.0188(11) Uani 1 1 d . . . . .
C7 C -0.2794(9) 0.2575(5) -0.1747(4) 0.0183(11) Uani 1 1 d . . . . .
H7 H -0.273633 0.268124 -0.234229 0.022 Uiso 1 1 calc R U . . .
C37 C 0.5372(9) 0.3784(6) 0.3251(4) 0.0210(12) Uani 1 1 d . . . . .
H37A H 0.619039 0.378320 0.382997 0.025 Uiso 1 1 calc R U . . .
H37B H 0.637952 0.411177 0.285951 0.025 Uiso 1 1 calc R U . . .
C23 C 0.6924(9) 0.8359(6) 0.0459(4) 0.0203(12) Uani 1 1 d . . . . .
H23 H 0.805646 0.878631 0.018464 0.024 Uiso 1 1 calc R U . . .
C32 C 0.3140(8) 0.4835(5) 0.2478(4) 0.0169(11) Uani 1 1 d . . . . .
H32 H 0.431799 0.509324 0.214194 0.020 Uiso 1 1 calc R U . . .
C3 C -0.1655(9) 0.1755(6) -0.0461(4) 0.0219(12) Uani 1 1 d . . . . .
H3 H -0.078607 0.132149 -0.018691 0.026 Uiso 1 1 calc R U . . .
C14 C -0.2174(10) 0.7759(6) -0.2623(4) 0.0198(12) Uani 1 1 d . . . . .
H14 H -0.202080 0.868879 -0.230849 0.024 Uiso 1 1 calc R U . . .
C39 C 0.4625(11) 0.1736(6) 0.2048(4) 0.0274(14) Uani 1 1 d . . . . .
H39 H 0.458001 0.211547 0.153141 0.033 Uiso 1 1 calc R U . . .
C13 C -0.2913(9) 0.6742(6) -0.2028(4) 0.0181(11) Uani 1 1 d . . . . .
H13A H -0.430915 0.673164 -0.189979 0.022 Uiso 1 1 calc R U . . .
H13B H -0.189583 0.702086 -0.145576 0.022 Uiso 1 1 calc R U . . .
C19 C 0.1762(10) 0.8313(7) -0.2089(4) 0.0266(13) Uani 1 1 d . . . . .
H19 H 0.166232 0.789157 -0.158962 0.032 Uiso 1 1 calc R U . . .
C17 C -0.0309(10) 0.6277(6) -0.3309(4) 0.0216(12) Uani 1 1 d . . . . .
H17A H 0.010979 0.625816 -0.389872 0.026 Uiso 1 1 calc R U . . .
H17B H 0.061637 0.593429 -0.293113 0.026 Uiso 1 1 calc R U . . .
C1 C -0.0357(11) 0.1364(6) -0.2663(4) 0.0250(13) Uani 1 1 d . . . . .
H1A H -0.176828 0.088582 -0.302915 0.038 Uiso 1 1 calc R U . . .
H1B H 0.064278 0.094874 -0.287062 0.038 Uiso 1 1 calc R U . . .
H1C H 0.010202 0.231849 -0.271270 0.038 Uiso 1 1 calc R U . . .
C15 C -0.3830(10) 0.7342(6) -0.3483(4) 0.0235(13) Uani 1 1 d . . . . .
H15A H -0.343522 0.802204 -0.385961 0.028 Uiso 1 1 calc R U . . .
H15B H -0.522767 0.729695 -0.334000 0.028 Uiso 1 1 calc R U . . .
C21 C 0.9943(10) 0.8786(6) 0.2676(4) 0.0257(13) Uani 1 1 d . . . . .
H21A H 0.950122 0.783956 0.274285 0.039 Uiso 1 1 calc R U . . .
H21B H 0.922110 0.927585 0.303298 0.039 Uiso 1 1 calc R U . . .
H21C H 1.147666 0.920888 0.288081 0.039 Uiso 1 1 calc R U . . .
C40 C 0.5360(13) 0.0734(7) 0.2035(5) 0.0334(16) Uani 1 1 d . . . . .
C20 C 0.3481(12) 0.9356(8) -0.2055(5) 0.0383(17) Uani 1 1 d . . . . .
H20A H 0.472(14) 0.974(9) -0.144(6) 0.03(2) Uiso 1 1 d . . . . .
H40A H 0.513(14) 0.028(9) 0.245(6) 0.03(2) Uiso 1 1 d . . . . .
H20B H 0.336(18) 0.983(11) -0.253(7) 0.06(3) Uiso 1 1 d . . . . .
H5A H 0.819(15) 0.735(8) 0.428(6) 0.03(2) Uiso 1 1 d . . . . .
H40B H 0.608(14) 0.039(9) 0.152(6) 0.03(2) Uiso 1 1 d . . . . .
H6B H -0.008(12) 0.262(6) 0.545(4) 0.005(14) Uiso 1 1 d . . . . .
H8B H 0.360(12) 1.097(7) 0.568(4) 0.007(14) Uiso 1 1 d . . . . .
H5B H 0.656(15) 0.798(10) 0.425(6) 0.04(2) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C31 O4 H4 109.5 . . ?
C11 O2 H2 109.5 . . ?
C22 O3 C21 117.2(5) . . ?
C2 O1 C1 116.7(4) . . ?
H6A O6 H6B 100.2 . . ?
H5A O5 H5B 115(8) . . ?
H7A O7 H7B 104.5 . . ?
C36 N4 H4A 108.5 . . ?
C37 N4 H4A 108.5 . . ?
C37 N4 C36 108.1(4) . . ?
C37 N4 C32 107.9(4) . . ?
C32 N4 H4A 108.5 . . ?
C32 N4 C36 115.1(4) . . ?
C28 N3 C25 116.8(5) . . ?
H8A O8 H8B 97.5 . . ?
C16 N2 H2A 108.6 . . ?
C16 N2 C12 114.4(5) . . ?
C12 N2 H2A 108.6 . . ?
C17 N2 H2A 108.6 . . ?
C17 N2 C16 108.4(4) . . ?
C17 N2 C12 108.2(4) . . ?
C8 N1 C5 116.1(5) . . ?
N3 C25 C24 117.5(5) . . ?
N3 C25 C26 123.5(5) . . ?
C26 C25 C24 119.0(5) . . ?
N1 C5 C4 117.5(5) . . ?
N1 C5 C6 124.1(5) . . ?
C4 C5 C6 118.4(5) . . ?
N4 C36 H36A 109.9 . . ?
N4 C36 H36B 109.9 . . ?
N4 C36 C35 108.9(4) . . ?
H36A C36 H36B 108.3 . . ?
C35 C36 H36A 109.9 . . ?
C35 C36 H36B 109.9 . . ?
C29 C30 C26 118.4(5) . . ?
C29 C30 C31 120.7(5) . . ?
C26 C30 C31 120.9(5) . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(5) . . ?
C8 C9 H9 119.9 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.7(6) . . ?
C23 C24 H24 119.7 . . ?
C9 C10 C11 120.5(5) . . ?
C9 C10 C6 118.5(5) . . ?
C6 C10 C11 121.0(5) . . ?
N3 C28 H28 117.8 . . ?
N3 C28 C29 124.4(6) . . ?
C29 C28 H28 117.8 . . ?
C5 C4 H4B 119.7 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4B 119.7 . . ?
N1 C8 C9 124.2(6) . . ?
N1 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C30 C29 C28 119.8(6) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C25 C26 C30 117.1(5) . . ?
C25 C26 C27 119.7(5) . . ?
C27 C26 C30 123.2(5) . . ?
H33A C33 H33B 108.2 . . ?
C34 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
C32 C33 H33A 109.7 . . ?
C32 C33 H33B 109.7 . . ?
C32 C33 C34 109.7(4) . . ?
O4 C31 C30 111.0(4) . . ?
O4 C31 H31 109.1 . . ?
O4 C31 C32 111.0(4) . . ?
C30 C31 H31 109.1 . . ?
C30 C31 C32 107.6(4) . . ?
C32 C31 H31 109.1 . . ?
N2 C16 H16A 109.8 . . ?
N2 C16 H16B 109.8 . . ?
N2 C16 C15 109.4(4) . . ?
H16A C16 H16B 108.2 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
O2 C11 C10 110.7(5) . . ?
O2 C11 H11 109.1 . . ?
O2 C11 C12 110.8(4) . . ?
C10 C11 H11 109.1 . . ?
C10 C11 C12 108.0(4) . . ?
C12 C11 H11 109.1 . . ?
C36 C35 H35A 109.9 . . ?
C36 C35 H35B 109.9 . . ?
H35A C35 H35B 108.3 . . ?
C34 C35 C36 108.8(4) . . ?
C34 C35 H35A 109.9 . . ?
C34 C35 H35B 109.9 . . ?
C10 C6 C5 116.9(5) . . ?
C7 C6 C5 119.4(5) . . ?
C7 C6 C10 123.7(5) . . ?
C14 C18 H18 108.1 . . ?
C14 C18 C17 108.2(5) . . ?
C19 C18 H18 108.1 . . ?
C19 C18 C14 112.8(5) . . ?
C19 C18 C17 111.3(5) . . ?
C17 C18 H18 108.1 . . ?
O1 C2 C7 125.3(5) . . ?
O1 C2 C3 114.2(5) . . ?
C7 C2 C3 120.5(5) . . ?
N2 C12 C11 111.1(4) . . ?
N2 C12 H12 107.4 . . ?
N2 C12 C13 108.0(4) . . ?
C11 C12 H12 107.4 . . ?
C11 C12 C13 115.3(5) . . ?
C13 C12 H12 107.4 . . ?
C33 C34 H34 109.7 . . ?
C33 C34 C38 110.8(5) . . ?
C35 C34 C33 108.0(5) . . ?
C35 C34 H34 109.7 . . ?
C35 C34 C38 108.9(5) . . ?
C38 C34 H34 109.7 . . ?
C34 C38 H38 108.1 . . ?
C34 C38 C37 108.5(4) . . ?
C37 C38 H38 108.1 . . ?
C39 C38 C34 113.3(5) . . ?
C39 C38 H38 108.1 . . ?
C39 C38 C37 110.6(5) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 C26 119.5(5) . . ?
C22 C27 H27 120.2 . . ?
O3 C22 C27 125.4(5) . . ?
O3 C22 C23 114.0(5) . . ?
C27 C22 C23 120.5(5) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 C6 120.1(5) . . ?
C2 C7 H7 119.9 . . ?
N4 C37 C38 108.9(4) . . ?
N4 C37 H37A 109.9 . . ?
N4 C37 H37B 109.9 . . ?
C38 C37 H37A 109.9 . . ?
C38 C37 H37B 109.9 . . ?
H37A C37 H37B 108.3 . . ?
C24 C23 C22 120.5(5) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N4 C32 C33 108.4(4) . . ?
N4 C32 C31 112.0(4) . . ?
N4 C32 H32 107.1 . . ?
C33 C32 C31 114.8(5) . . ?
C33 C32 H32 107.1 . . ?
C31 C32 H32 107.1 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C18 C14 H14 109.7 . . ?
C13 C14 C18 111.0(5) . . ?
C13 C14 H14 109.7 . . ?
C15 C14 C18 108.2(5) . . ?
C15 C14 H14 109.7 . . ?
C15 C14 C13 108.5(5) . . ?
C38 C39 H39 117.6 . . ?
C40 C39 C38 124.8(6) . . ?
C40 C39 H39 117.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 C12 110.1(5) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C18 C19 H19 118.1 . . ?
C20 C19 C18 123.8(6) . . ?
C20 C19 H19 118.1 . . ?
N2 C17 C18 109.4(5) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C16 C15 H15A 109.9 . . ?
C16 C15 H15B 109.9 . . ?
C14 C15 C16 109.0(5) . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C39 C40 H40A 116(6) . . ?
C39 C40 H40B 125(5) . . ?
H40A C40 H40B 119(7) . . ?
C19 C20 H20A 119(4) . . ?
C19 C20 H20B 113(7) . . ?
H20A C20 H20B 126(8) . . ?
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 H4 0.8400 . ?
O4 C31 1.426(7) . ?
O2 H2 0.8400 . ?
O2 C11 1.420(7) . ?
O3 C22 1.355(8) . ?
O3 C21 1.425(7) . ?
O1 C2 1.350(8) . ?
O1 C1 1.430(7) . ?
O6 H6A 0.8499 . ?
O6 H6B 0.84(7) . ?
O5 H5A 0.87(10) . ?
O5 H5B 0.87(10) . ?
O7 H7A 0.8502 . ?
O7 H7B 0.8495 . ?
N4 H4A 1.0000 . ?
N4 C36 1.522(7) . ?
N4 C37 1.502(8) . ?
N4 C32 1.518(6) . ?
N3 C25 1.371(8) . ?
N3 C28 1.309(9) . ?
O8 H8A 0.8503 . ?
O8 H8B 0.86(8) . ?
N2 H2A 1.0000 . ?
N2 C16 1.513(8) . ?
N2 C12 1.518(7) . ?
N2 C17 1.503(8) . ?
N1 C5 1.367(8) . ?
N1 C8 1.326(8) . ?
C25 C24 1.422(9) . ?
C25 C26 1.420(8) . ?
C5 C4 1.429(8) . ?
C5 C6 1.430(8) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C35 1.534(8) . ?
C30 C29 1.366(8) . ?
C30 C26 1.427(8) . ?
C30 C31 1.522(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(9) . ?
C9 C8 1.411(9) . ?
C24 H24 0.9500 . ?
C24 C23 1.364(9) . ?
C10 C11 1.526(7) . ?
C10 C6 1.424(8) . ?
C28 H28 0.9500 . ?
C28 C29 1.410(8) . ?
C4 H4B 0.9500 . ?
C4 C3 1.364(9) . ?
C8 H8 0.9500 . ?
C29 H29 0.9500 . ?
C26 C27 1.425(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.537(7) . ?
C33 C32 1.537(7) . ?
C31 H31 1.0000 . ?
C31 C32 1.537(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.533(9) . ?
C11 H11 1.0000 . ?
C11 C12 1.534(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C34 1.527(8) . ?
C6 C7 1.419(8) . ?
C18 H18 1.0000 . ?
C18 C14 1.545(9) . ?
C18 C19 1.503(8) . ?
C18 C17 1.555(8) . ?
C2 C7 1.380(8) . ?
C2 C3 1.408(8) . ?
C12 H12 1.0000 . ?
C12 C13 1.541(8) . ?
C34 H34 1.0000 . ?
C34 C38 1.548(8) . ?
C38 H38 1.0000 . ?
C38 C37 1.551(8) . ?
C38 C39 1.499(9) . ?
C27 H27 0.9500 . ?
C27 C22 1.383(9) . ?
C22 C23 1.422(8) . ?
C7 H7 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C23 H23 0.9500 . ?
C32 H32 1.0000 . ?
C3 H3 0.9500 . ?
C14 H14 1.0000 . ?
C14 C13 1.532(8) . ?
C14 C15 1.531(8) . ?
C39 H39 0.9500 . ?
C39 C40 1.308(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C19 H19 0.9500 . ?
C19 C20 1.320(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C40 H40A 0.86(9) . ?
C40 H40B 1.07(9) . ?
C20 H20A 1.11(9) . ?
C20 H20B 0.96(11) . ?
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
O4 C31 C32 N4 -74.5(5) . . . . ?
O4 C31 C32 C33 49.5(6) . . . . ?
O2 C11 C12 N2 -75.8(6) . . . . ?
O2 C11 C12 C13 47.5(6) . . . . ?
O3 C22 C23 C24 -176.4(5) . . . . ?
O1 C2 C7 C6 177.7(5) . . . . ?
O1 C2 C3 C4 -176.0(5) . . . . ?
N4 C36 C35 C34 11.3(6) . . . . ?
N3 C25 C24 C23 -179.9(5) . . . . ?
N3 C25 C26 C30 1.5(8) . . . . ?
N3 C25 C26 C27 -179.3(5) . . . . ?
N3 C28 C29 C30 0.5(9) . . . . ?
N2 C16 C15 C14 6.3(7) . . . . ?
N2 C12 C13 C14 -3.4(6) . . . . ?
N1 C5 C4 C3 179.9(5) . . . . ?
N1 C5 C6 C10 2.3(8) . . . . ?
N1 C5 C6 C7 -178.3(5) . . . . ?
C25 N3 C28 C29 -1.3(8) . . . . ?
C25 C24 C23 C22 -1.0(8) . . . . ?
C25 C26 C27 C22 -0.9(8) . . . . ?
C5 N1 C8 C9 -1.2(8) . . . . ?
C5 C4 C3 C2 -2.5(8) . . . . ?
C5 C6 C7 C2 -0.7(8) . . . . ?
C36 N4 C37 C38 57.0(6) . . . . ?
C36 N4 C32 C33 -56.7(6) . . . . ?
C36 N4 C32 C31 70.8(6) . . . . ?
C36 C35 C34 C33 -67.2(6) . . . . ?
C36 C35 C34 C38 53.2(6) . . . . ?
C30 C26 C27 C22 178.3(5) . . . . ?
C30 C31 C32 N4 163.9(4) . . . . ?
C30 C31 C32 C33 -72.1(6) . . . . ?
C9 C10 C11 O2 -17.2(7) . . . . ?
C9 C10 C11 C12 104.3(6) . . . . ?
C9 C10 C6 C5 -2.2(7) . . . . ?
C9 C10 C6 C7 178.5(5) . . . . ?
C24 C25 C26 C30 -176.7(5) . . . . ?
C24 C25 C26 C27 2.5(8) . . . . ?
C10 C9 C8 N1 1.2(9) . . . . ?
C10 C11 C12 N2 162.8(5) . . . . ?
C10 C11 C12 C13 -73.8(6) . . . . ?
C10 C6 C7 C2 178.6(5) . . . . ?
C28 N3 C25 C24 178.5(5) . . . . ?
C28 N3 C25 C26 0.3(8) . . . . ?
C4 C5 C6 C10 -177.6(5) . . . . ?
C4 C5 C6 C7 1.8(7) . . . . ?
C8 N1 C5 C4 179.2(5) . . . . ?
C8 N1 C5 C6 -0.6(8) . . . . ?
C8 C9 C10 C11 -178.4(5) . . . . ?
C8 C9 C10 C6 0.6(8) . . . . ?
C29 C30 C26 C25 -2.3(7) . . . . ?
C29 C30 C26 C27 178.5(5) . . . . ?
C29 C30 C31 O4 -17.7(7) . . . . ?
C29 C30 C31 C32 103.9(6) . . . . ?
C26 C25 C24 C23 -1.6(8) . . . . ?
C26 C30 C29 C28 1.4(8) . . . . ?
C26 C30 C31 O4 164.4(4) . . . . ?
C26 C30 C31 C32 -74.0(6) . . . . ?
C26 C27 C22 O3 177.3(5) . . . . ?
C26 C27 C22 C23 -1.7(8) . . . . ?
C33 C34 C38 C37 53.7(6) . . . . ?
C33 C34 C38 C39 -69.5(6) . . . . ?
C31 C30 C29 C28 -176.5(5) . . . . ?
C31 C30 C26 C25 175.6(5) . . . . ?
C31 C30 C26 C27 -3.5(8) . . . . ?
C16 N2 C12 C11 71.3(6) . . . . ?
C16 N2 C12 C13 -56.1(6) . . . . ?
C16 N2 C17 C18 58.6(6) . . . . ?
C11 C10 C6 C5 176.8(5) . . . . ?
C11 C10 C6 C7 -2.6(8) . . . . ?
C11 C12 C13 C14 -128.3(5) . . . . ?
C35 C34 C38 C37 -64.9(6) . . . . ?
C35 C34 C38 C39 171.8(5) . . . . ?
C6 C5 C4 C3 -0.2(8) . . . . ?
C6 C10 C11 O2 163.9(4) . . . . ?
C6 C10 C11 C12 -74.6(6) . . . . ?
C18 C14 C13 C12 -56.7(6) . . . . ?
C18 C14 C15 C16 57.0(6) . . . . ?
C12 N2 C16 C15 54.9(6) . . . . ?
C12 N2 C17 C18 -66.0(6) . . . . ?
C34 C33 C32 N4 -1.2(6) . . . . ?
C34 C33 C32 C31 -127.2(5) . . . . ?
C34 C38 C37 N4 7.9(6) . . . . ?
C34 C38 C39 C40 -127.0(7) . . . . ?
C27 C22 C23 C24 2.7(8) . . . . ?
C7 C2 C3 C4 3.6(8) . . . . ?
C37 N4 C36 C35 -69.4(6) . . . . ?
C37 N4 C32 C33 64.0(5) . . . . ?
C37 N4 C32 C31 -168.4(4) . . . . ?
C37 C38 C39 C40 111.0(8) . . . . ?
C32 N4 C36 C35 51.2(6) . . . . ?
C32 N4 C37 C38 -68.0(5) . . . . ?
C32 C33 C34 C35 61.4(6) . . . . ?
C32 C33 C34 C38 -57.8(6) . . . . ?
C3 C2 C7 C6 -2.0(8) . . . . ?
C14 C18 C19 C20 -122.1(7) . . . . ?
C14 C18 C17 N2 5.1(6) . . . . ?
C39 C38 C37 N4 132.8(5) . . . . ?
C13 C14 C15 C16 -63.5(6) . . . . ?
C19 C18 C14 C13 -68.2(6) . . . . ?
C19 C18 C14 C15 172.9(5) . . . . ?
C19 C18 C17 N2 129.5(5) . . . . ?
C17 N2 C16 C15 -65.9(6) . . . . ?
C17 N2 C12 C11 -167.8(4) . . . . ?
C17 N2 C12 C13 64.8(6) . . . . ?
C17 C18 C14 C13 55.3(6) . . . . ?
C17 C18 C14 C15 -63.6(6) . . . . ?
C17 C18 C19 C20 116.1(8) . . . . ?
C1 O1 C2 C7 -0.2(8) . . . . ?
C1 O1 C2 C3 179.5(5) . . . . ?
C15 C14 C13 C12 62.1(6) . . . . ?
C21 O3 C22 C27 -0.8(8) . . . . ?
C21 O3 C22 C23 178.3(5) . . . . ?
