# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Nathan Schultheiss'
_publ_contact_author_email       NATHAN.SCHULTHEISS@APTUIT.COM

_publ_section_title              
;
Attempted construction of minoxidil:carboxylic
acid cocrystals; 7 salts and 1 cocrystal resulted
;
loop_
_publ_author_name
'Nathan Schultheiss'
'John Desper'
'Keith Lorimer'
'Skylar Wolfe'

# Attachment '_2_.cif'

data_ns0802m
_database_code_depnum_ccdc_archive 'CCDC 733876'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3189-81-07 minoxidil : L-tartaric acid
;
_chemical_name_common            '3189-81-07 minoxidil'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O)4 (C4 H6 O6)2 (H2O)
;
_chemical_formula_sum            'C44 H74 N20 O17'
_chemical_formula_weight         1155.22
_chemical_absolute_configuration unk

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

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'

_cell_length_a                   19.283(2)
_cell_length_b                   9.7242(13)
_cell_length_c                   30.545(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.048(7)
_cell_angle_gamma                90.00
_cell_volume                     5531.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4300
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      31.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9840
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20228
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         31.70
_reflns_number_total             20228
_reflns_number_gt                18020
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+1.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         20228
_refine_ls_number_parameters     808
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1S O 0.41613(18) 0.5469(3) 0.52709(7) 0.0621(9) Uani 0.640(3) 1 d P A 1
O2S O 0.3858(3) 0.6759(5) 0.52485(13) 0.0621(9) Uani 0.360(3) 1 d P A 2
N11_1 N 0.56820(6) 0.64094(13) 0.11356(4) 0.0153(2) Uani 1 1 d . . .
O11_1 O 0.52044(5) 0.70136(12) 0.13442(3) 0.01804(19) Uani 1 1 d . . .
H11_1 H 0.4956(11) 0.613(2) 0.1455(7) 0.022 Uiso 1 1 d . . .
C12_1 C 0.54386(7) 0.59130(16) 0.07051(4) 0.0164(2) Uani 1 1 d . . .
N12_1 N 0.47314(7) 0.60213(16) 0.05159(4) 0.0223(3) Uani 1 1 d . . .
H12A_1 H 0.4537(12) 0.569(3) 0.0235(7) 0.027 Uiso 1 1 d . . .
H12B_1 H 0.4446(12) 0.617(3) 0.0717(7) 0.027 Uiso 1 1 d . . .
N13_1 N 0.58742(6) 0.53582(14) 0.04823(4) 0.0172(2) Uani 1 1 d . . .
C14_1 C 0.65923(7) 0.53019(15) 0.06956(4) 0.0154(2) Uani 1 1 d . . .
C15_1 C 0.68746(7) 0.59334(16) 0.11155(4) 0.0161(2) Uani 1 1 d . . .
H15_1 H 0.7379 0.5981 0.1243 0.019 Uiso 1 1 calc R . .
C16_1 C 0.64016(7) 0.64892(15) 0.13419(4) 0.0151(2) Uani 1 1 d . . .
N16_1 N 0.65842(7) 0.71130(15) 0.17433(4) 0.0189(2) Uani 1 1 d . . .
H16A_1 H 0.6206(11) 0.724(2) 0.1890(7) 0.023 Uiso 1 1 d . . .
H16B_1 H 0.6997(12) 0.709(3) 0.1882(7) 0.023 Uiso 1 1 d . . .
N21_1 N 0.70079(7) 0.45857(14) 0.04785(4) 0.0183(2) Uani 1 1 d . . .
C22_1 C 0.67320(9) 0.42485(18) -0.00041(5) 0.0251(3) Uani 1 1 d . . .
H22A_1 H 0.6798 0.5053 -0.0188 0.030 Uiso 1 1 calc R . .
H22B_1 H 0.6211 0.4060 -0.0069 0.030 Uiso 1 1 calc R . .
C23_1 C 0.71044(10) 0.30081(19) -0.01459(5) 0.0273(3) Uani 1 1 d . . .
H23A_1 H 0.6969 0.2167 -0.0005 0.033 Uiso 1 1 calc R . .
H23B_1 H 0.6944 0.2897 -0.0479 0.033 Uiso 1 1 calc R . .
C24_1 C 0.79148(11) 0.3183(2) -0.00019(6) 0.0315(4) Uani 1 1 d . . .
H24A_1 H 0.8056 0.4010 -0.0147 0.038 Uiso 1 1 calc R . .
H24B_1 H 0.8151 0.2373 -0.0096 0.038 Uiso 1 1 calc R . .
C25_1 C 0.81466(9) 0.3334(2) 0.05113(6) 0.0269(3) Uani 1 1 d . . .
H25A_1 H 0.8675 0.3431 0.0612 0.032 Uiso 1 1 calc R . .
H25B_1 H 0.8011 0.2496 0.0654 0.032 Uiso 1 1 calc R . .
C26_1 C 0.77946(8) 0.45879(17) 0.06647(5) 0.0208(3) Uani 1 1 d . . .
H26A_1 H 0.7909 0.4599 0.1000 0.025 Uiso 1 1 calc R . .
H26B_1 H 0.7996 0.5434 0.0566 0.025 Uiso 1 1 calc R . .
N11_2 N 0.27745(6) -0.13692(14) 0.21243(4) 0.0176(2) Uani 1 1 d . . .
O11_2 O 0.33688(5) -0.09914(12) 0.24646(3) 0.0192(2) Uani 1 1 d . . .
H11_2 H 0.3628(12) -0.011(3) 0.2329(7) 0.023 Uiso 1 1 d . . .
C12_2 C 0.28677(8) -0.20809(16) 0.17588(5) 0.0182(3) Uani 1 1 d . . .
N12_2 N 0.35378(7) -0.22126(16) 0.17165(4) 0.0224(3) Uani 1 1 d . . .
H12A_2 H 0.3637(12) -0.283(3) 0.1514(8) 0.027 Uiso 1 1 d . . .
H12B_2 H 0.3906(13) -0.194(3) 0.1921(8) 0.027 Uiso 1 1 d . . .
N13_2 N 0.23153(7) -0.25831(15) 0.14462(4) 0.0199(2) Uani 1 1 d . . .
C14_2 C 0.16423(8) -0.23800(16) 0.14934(5) 0.0189(3) Uani 1 1 d . . .
C15_2 C 0.15147(8) -0.15883(16) 0.18465(5) 0.0190(3) Uani 1 1 d . . .
H15_2 H 0.1038 -0.1403 0.1863 0.023 Uiso 1 1 calc R . .
C16_2 C 0.20985(8) -0.10811(16) 0.21712(5) 0.0182(3) Uani 1 1 d . . .
N16_2 N 0.20633(7) -0.03423(15) 0.25339(4) 0.0211(2) Uani 1 1 d . . .
H16B_2 H 0.2443(12) 0.011(3) 0.2686(8) 0.025 Uiso 1 1 d . . .
H16A_2 H 0.1650(12) 0.015(3) 0.2525(7) 0.025 Uiso 1 1 d . . .
N21_2 N 0.11041(7) -0.29906(17) 0.11776(4) 0.0244(3) Uani 1 1 d . . .
C22_2 C 0.03462(9) -0.2785(2) 0.11562(7) 0.0341(4) Uani 1 1 d . . .
H22A_2 H 0.0137 -0.2116 0.0913 0.041 Uiso 1 1 calc R . .
H22B_2 H 0.0301 -0.2398 0.1447 0.041 Uiso 1 1 calc R . .
C23_2 C -0.00679(9) -0.4132(2) 0.10623(6) 0.0333(4) Uani 1 1 d . . .
H23A_2 H -0.0586 -0.3945 0.1017 0.040 Uiso 1 1 calc R . .
H23B_2 H 0.0090 -0.4746 0.1328 0.040 Uiso 1 1 calc R . .
C24_2 C 0.00476(10) -0.4850(2) 0.06442(6) 0.0324(4) Uani 1 1 d . . .
H24A_2 H -0.0186 -0.5765 0.0611 0.039 Uiso 1 1 calc R . .
H24B_2 H -0.0174 -0.4302 0.0371 0.039 Uiso 1 1 calc R . .
C25_2 C 0.08449(10) -0.5017(2) 0.06870(7) 0.0342(4) Uani 1 1 d . . .
H25A_2 H 0.1053 -0.5656 0.0939 0.041 Uiso 1 1 calc R . .
H25B_2 H 0.0915 -0.5421 0.0404 0.041 Uiso 1 1 calc R . .
C26_2 C 0.12316(9) -0.3649(2) 0.07750(5) 0.0282(3) Uani 1 1 d . . .
H26A_2 H 0.1753 -0.3795 0.0819 0.034 Uiso 1 1 calc R . .
H26B_2 H 0.1059 -0.3041 0.0509 0.034 Uiso 1 1 calc R . .
N11_3 N 0.61744(6) 1.08201(13) 0.25457(4) 0.0166(2) Uani 1 1 d . . .
O11_3 O 0.56397(5) 1.03766(12) 0.21754(3) 0.0190(2) Uani 1 1 d . . .
H11_3 H 0.5442(11) 0.957(3) 0.2270(7) 0.023 Uiso 1 1 d . . .
C12_3 C 0.59961(7) 1.16358(16) 0.28644(4) 0.0178(3) Uani 1 1 d . . .
N12_3 N 0.52955(7) 1.18068(17) 0.28282(5) 0.0253(3) Uani 1 1 d . . .
H12A_3 H 0.5146(12) 1.239(3) 0.3020(8) 0.030 Uiso 1 1 d . . .
H12B_3 H 0.5017(13) 1.145(3) 0.2628(8) 0.030 Uiso 1 1 d . . .
N13_3 N 0.64843(6) 1.22125(14) 0.31965(4) 0.0184(2) Uani 1 1 d . . .
C14_3 C 0.71910(7) 1.20135(16) 0.32118(4) 0.0170(2) Uani 1 1 d . . .
C15_3 C 0.74049(7) 1.12472(16) 0.28787(5) 0.0171(2) Uani 1 1 d . . .
H15_3 H 0.7899 1.1132 0.2891 0.021 Uiso 1 1 calc R . .
C16_3 C 0.68781(7) 1.06667(15) 0.25334(4) 0.0156(2) Uani 1 1 d . . .
N16_3 N 0.69921(7) 0.99591(15) 0.21855(4) 0.0195(2) Uani 1 1 d . . .
H16B_3 H 0.6626(12) 0.970(3) 0.1975(7) 0.023 Uiso 1 1 d . . .
H16A_3 H 0.7434(12) 0.986(3) 0.2187(7) 0.023 Uiso 1 1 d . . .
N21_3 N 0.76688(7) 1.26119(16) 0.35640(4) 0.0239(3) Uani 1 1 d . . .
C22_3 C 0.84471(8) 1.2465(2) 0.36489(6) 0.0277(3) Uani 1 1 d . . .
H22A_3 H 0.8561 1.1985 0.3390 0.033 Uiso 1 1 calc R . .
H22B_3 H 0.8634 1.1903 0.3925 0.033 Uiso 1 1 calc R . .
C23_3 C 0.88097(10) 1.3877(2) 0.37119(6) 0.0322(4) Uani 1 1 d . . .
H23A_3 H 0.8664 1.4400 0.3425 0.039 Uiso 1 1 calc R . .
H23B_3 H 0.9338 1.3758 0.3789 0.039 Uiso 1 1 calc R . .
C24_3 C 0.86007(10) 1.4683(2) 0.40895(6) 0.0317(4) Uani 1 1 d . . .
H24A_3 H 0.8796 1.4216 0.4384 0.038 Uiso 1 1 calc R . .
H24B_3 H 0.8809 1.5619 0.4110 0.038 Uiso 1 1 calc R . .
C25_3 C 0.77878(10) 1.4779(2) 0.39911(6) 0.0303(3) Uani 1 1 d . . .
H25A_3 H 0.7600 1.5339 0.3715 0.036 Uiso 1 1 calc R . .
H25B_3 H 0.7657 1.5243 0.4247 0.036 Uiso 1 1 calc R . .
C26_3 C 0.74454(9) 1.33521(19) 0.39225(5) 0.0254(3) Uani 1 1 d . . .
H26A_3 H 0.7592 1.2825 0.4209 0.030 Uiso 1 1 calc R . .
H26B_3 H 0.6916 1.3442 0.3839 0.030 Uiso 1 1 calc R . .
N11_4 N 0.31885(6) 0.35455(14) 0.37297(4) 0.0186(2) Uani 1 1 d . . .
O11_4 O 0.37048(6) 0.27691(13) 0.36019(4) 0.0227(2) Uani 1 1 d . . .
H11_4 H 0.3973(13) 0.325(3) 0.3464(8) 0.027 Uiso 1 1 d . . .
C12_4 C 0.33418(8) 0.41201(18) 0.41562(5) 0.0214(3) Uani 1 1 d . . .
N12_4 N 0.40320(8) 0.4114(2) 0.43946(5) 0.0312(3) Uani 1 1 d . . .
H12A_4 H 0.4131(13) 0.454(3) 0.4642(9) 0.037 Uiso 1 1 d . . .
H12B_4 H 0.4340(14) 0.403(3) 0.4248(9) 0.037 Uiso 1 1 d . . .
N13_4 N 0.28360(7) 0.46515(17) 0.43247(4) 0.0251(3) Uani 1 1 d . . .
C14_4 C 0.21370(8) 0.45616(17) 0.40749(4) 0.0196(3) Uani 1 1 d . . .
C15_4 C 0.19497(7) 0.39126(16) 0.36538(4) 0.0175(2) Uani 1 1 d . . .
H15_4 H 0.1461 0.3840 0.3487 0.021 Uiso 1 1 calc R . .
C16_4 C 0.24883(7) 0.33793(16) 0.34846(5) 0.0176(2) Uani 1 1 d . . .
N16_4 N 0.23726(7) 0.26792(16) 0.30980(4) 0.0213(2) Uani 1 1 d . . .
H16A_4 H 0.2727(12) 0.251(3) 0.2954(8) 0.026 Uiso 1 1 d . . .
H16B_4 H 0.1963(12) 0.260(3) 0.2929(7) 0.026 Uiso 1 1 d . . .
N21_4 N 0.16392(7) 0.51607(18) 0.42544(4) 0.0267(3) Uani 1 1 d . . .
C22_4 C 0.18031(12) 0.5468(2) 0.47408(6) 0.0344(4) Uani 1 1 d . . .
H22A_4 H 0.2330 0.5521 0.4866 0.041 Uiso 1 1 calc R . .
H22B_4 H 0.1622 0.4713 0.4898 0.041 Uiso 1 1 calc R . .
C23_4 C 0.14666(12) 0.6813(2) 0.48307(7) 0.0394(5) Uani 1 1 d . . .
H23A_4 H 0.1550 0.6945 0.5162 0.047 Uiso 1 1 calc R . .
H23B_4 H 0.1697 0.7586 0.4711 0.047 Uiso 1 1 calc R . .
C24_4 C 0.06667(13) 0.6821(3) 0.46088(8) 0.0476(6) Uani 1 1 d . . .
H24A_4 H 0.0463 0.7729 0.4653 0.057 Uiso 1 1 calc R . .
H24B_4 H 0.0427 0.6114 0.4751 0.057 Uiso 1 1 calc R . .
C25_4 C 0.05336(10) 0.6521(2) 0.41003(7) 0.0368(4) Uani 1 1 d . . .
H25A_4 H 0.0010 0.6482 0.3959 0.044 Uiso 1 1 calc R . .
H25B_4 H 0.0735 0.7279 0.3955 0.044 Uiso 1 1 calc R . .
C26_4 C 0.08750(9) 0.5171(2) 0.40171(6) 0.0301(4) Uani 1 1 d . . .
H26A_4 H 0.0630 0.4397 0.4126 0.036 Uiso 1 1 calc R . .
H26B_4 H 0.0817 0.5047 0.3688 0.036 Uiso 1 1 calc R . .
O10_5 O 0.47577(6) 0.49948(13) 0.16770(4) 0.0218(2) Uani 1 1 d . . .
C11_5 C 0.41155(8) 0.47077(17) 0.14565(5) 0.0191(3) Uani 1 1 d . . .
O11_5 O 0.37330(6) 0.54006(13) 0.11423(4) 0.0238(2) Uani 1 1 d . . .
C12_5 C 0.37995(9) 0.34003(18) 0.16046(5) 0.0227(3) Uani 1 1 d . . .
H12A_5 H 0.4092 0.2597 0.1553 0.027 Uiso 1 1 calc R . .
O12_5 O 0.30868(8) 0.3206(2) 0.13499(4) 0.0409(4) Uani 1 1 d . . .
H12_5 H 0.2955(16) 0.393(4) 0.1235(11) 0.049 Uiso 1 1 d . . .
C13_5 C 0.38371(7) 0.34792(16) 0.21115(4) 0.0163(2) Uani 1 1 d . . .
H13A_5 H 0.4350 0.3573 0.2287 0.020 Uiso 1 1 calc R . .
O13_5 O 0.34518(6) 0.46456(12) 0.21897(4) 0.0223(2) Uani 1 1 d . . .
H13_5 H 0.3703(13) 0.512(3) 0.2365(8) 0.027 Uiso 1 1 d . . .
C14_5 C 0.35321(7) 0.21478(16) 0.22492(4) 0.0165(2) Uani 1 1 d . . .
O14_5 O 0.29671(5) 0.21525(12) 0.23697(3) 0.0201(2) Uani 1 1 d . . .
O15_5 O 0.39021(6) 0.10716(12) 0.22228(4) 0.0231(2) Uani 1 1 d . . .
O10_6 O 0.50077(6) 0.83444(13) 0.24197(4) 0.0230(2) Uani 1 1 d . . .
C11_6 C 0.53585(7) 0.72585(16) 0.25525(4) 0.0181(3) Uani 1 1 d . . .
O11_6 O 0.59781(5) 0.69899(13) 0.25218(4) 0.0216(2) Uani 1 1 d . . .
C12_6 C 0.49747(7) 0.61651(16) 0.27631(5) 0.0178(3) Uani 1 1 d . . .
H12A_6 H 0.4936 0.5317 0.2573 0.021 Uiso 1 1 calc R . .
O12_6 O 0.42684(6) 0.65584(14) 0.27676(4) 0.0245(2) Uani 1 1 d . . .
H12_6 H 0.4186(12) 0.743(3) 0.2670(8) 0.029 Uiso 1 1 d . . .
C13_6 C 0.54061(8) 0.5795(2) 0.32409(5) 0.0259(3) Uani 1 1 d . . .
H13A_6 H 0.5847 0.5281 0.3223 0.031 Uiso 1 1 calc R . .
O13_6 O 0.56114(10) 0.7015(2) 0.34980(5) 0.0508(5) Uani 1 1 d . . .
H13_6 H 0.5499(17) 0.681(4) 0.3765(11) 0.061 Uiso 1 1 d . . .
C14_6 C 0.49549(8) 0.48840(18) 0.34712(5) 0.0229(3) Uani 1 1 d . . .
O14_6 O 0.49688(8) 0.51657(18) 0.38712(4) 0.0409(4) Uani 1 1 d . . .
O15_6 O 0.45916(6) 0.39321(13) 0.32401(4) 0.0247(2) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N11_1 C12_1 1.3645(16) . ?
N11_1 C16_1 1.3691(17) . ?
N11_1 O11_1 1.3799(15) . ?
O11_1 H11_1 1.08(2) . ?
C12_1 N13_1 1.3253(18) . ?
C12_1 N12_1 1.3399(17) . ?
N12_1 H12A_1 0.90(2) . ?
N12_1 H12B_1 0.94(2) . ?
N13_1 C14_1 1.3699(17) . ?
C14_1 N21_1 1.3577(18) . ?
C14_1 C15_1 1.3985(18) . ?
C15_1 C16_1 1.3893(19) . ?
C15_1 H15_1 0.9500 . ?
C16_1 N16_1 1.3306(17) . ?
N16_1 H16A_1 0.96(2) . ?
N16_1 H16B_1 0.80(2) . ?
N21_1 C22_1 1.4683(17) . ?
N21_1 C26_1 1.4753(19) . ?
C22_1 C23_1 1.523(2) . ?
C22_1 H22A_1 0.9900 . ?
C22_1 H22B_1 0.9900 . ?
C23_1 C24_1 1.519(3) . ?
C23_1 H23A_1 0.9900 . ?
C23_1 H23B_1 0.9900 . ?
C24_1 C25_1 1.521(2) . ?
C24_1 H24A_1 0.9900 . ?
C24_1 H24B_1 0.9900 . ?
C25_1 C26_1 1.527(2) . ?
C25_1 H25A_1 0.9900 . ?
C25_1 H25B_1 0.9900 . ?
C26_1 H26A_1 0.9900 . ?
C26_1 H26B_1 0.9900 . ?
N11_2 C12_2 1.3644(19) . ?
N11_2 C16_2 1.3765(19) . ?
N11_2 O11_2 1.3821(14) . ?
O11_2 H11_2 1.13(2) . ?
C12_2 N13_2 1.3254(18) . ?
C12_2 N12_2 1.338(2) . ?
N12_2 H12A_2 0.92(3) . ?
N12_2 H12B_2 0.86(2) . ?
N13_2 C14_2 1.3569(19) . ?
C14_2 N21_2 1.3565(18) . ?
C14_2 C15_2 1.398(2) . ?
C15_2 C16_2 1.384(2) . ?
C15_2 H15_2 0.9500 . ?
C16_2 N16_2 1.337(2) . ?
N16_2 H16B_2 0.88(2) . ?
N16_2 H16A_2 0.92(2) . ?
N21_2 C22_2 1.459(2) . ?
N21_2 C26_2 1.463(2) . ?
C22_2 C23_2 1.522(3) . ?
C22_2 H22A_2 0.9900 . ?
C22_2 H22B_2 0.9900 . ?
C23_2 C24_2 1.522(2) . ?
C23_2 H23A_2 0.9900 . ?
C23_2 H23B_2 0.9900 . ?
C24_2 C25_2 1.517(3) . ?
C24_2 H24A_2 0.9900 . ?
C24_2 H24B_2 0.9900 . ?
C25_2 C26_2 1.514(3) . ?
C25_2 H25A_2 0.9900 . ?
C25_2 H25B_2 0.9900 . ?
C26_2 H26A_2 0.9900 . ?
C26_2 H26B_2 0.9900 . ?
N11_3 C12_3 1.3670(18) . ?
N11_3 C16_3 1.3751(18) . ?
N11_3 O11_3 1.3868(14) . ?
O11_3 H11_3 0.95(3) . ?
C12_3 N13_3 1.3167(18) . ?
C12_3 N12_3 1.3370(19) . ?
N12_3 H12A_3 0.91(3) . ?
N12_3 H12B_3 0.78(3) . ?
N13_3 C14_3 1.3652(18) . ?
C14_3 N21_3 1.3528(18) . ?
C14_3 C15_3 1.407(2) . ?
C15_3 C16_3 1.3808(18) . ?
C15_3 H15_3 0.9500 . ?
C16_3 N16_3 1.3312(19) . ?
N16_3 H16B_3 0.86(2) . ?
N16_3 H16A_3 0.86(2) . ?
N21_3 C22_3 1.462(2) . ?
N21_3 C26_3 1.465(2) . ?
C22_3 C23_3 1.529(3) . ?
C22_3 H22A_3 0.9900 . ?
C22_3 H22B_3 0.9900 . ?
C23_3 C24_3 1.533(3) . ?
C23_3 H23A_3 0.9900 . ?
C23_3 H23B_3 0.9900 . ?
C24_3 C25_3 1.520(3) . ?
C24_3 H24A_3 0.9900 . ?
C24_3 H24B_3 0.9900 . ?
C25_3 C26_3 1.528(3) . ?
C25_3 H25A_3 0.9900 . ?
C25_3 H25B_3 0.9900 . ?
C26_3 H26A_3 0.9900 . ?
C26_3 H26B_3 0.9900 . ?
N11_4 C16_4 1.3727(17) . ?
N11_4 C12_4 1.3773(19) . ?
N11_4 O11_4 1.3839(17) . ?
O11_4 H11_4 0.88(3) . ?
C12_4 N13_4 1.321(2) . ?
C12_4 N12_4 1.3410(19) . ?
N12_4 H12A_4 0.84(3) . ?
N12_4 H12B_4 0.84(3) . ?
N13_4 C14_4 1.3683(18) . ?
C14_4 N21_4 1.354(2) . ?
C14_4 C15_4 1.3936(19) . ?
C15_4 C16_4 1.376(2) . ?
C15_4 H15_4 0.9500 . ?
C16_4 N16_4 1.3308(19) . ?
N16_4 H16A_4 0.92(2) . ?
N16_4 H16B_4 0.83(2) . ?
N21_4 C26_4 1.464(2) . ?
N21_4 C22_4 1.467(2) . ?
C22_4 C23_4 1.517(3) . ?
C22_4 H22A_4 0.9900 . ?
C22_4 H22B_4 0.9900 . ?
C23_4 C24_4 1.515(3) . ?
C23_4 H23A_4 0.9900 . ?
C23_4 H23B_4 0.9900 . ?
C24_4 C25_4 1.535(3) . ?
C24_4 H24A_4 0.9900 . ?
C24_4 H24B_4 0.9900 . ?
C25_4 C26_4 1.520(3) . ?
C25_4 H25A_4 0.9900 . ?
C25_4 H25B_4 0.9900 . ?
C26_4 H26A_4 0.9900 . ?
C26_4 H26B_4 0.9900 . ?
O10_5 C11_5 1.2776(17) . ?
O10_5 H11_1 1.40(2) . ?
C11_5 O11_5 1.2454(19) . ?
C11_5 C12_5 1.528(2) . ?
C12_5 O12_5 1.405(2) . ?
C12_5 C13_5 1.5330(19) . ?
C12_5 H12A_5 1.0000 . ?
O12_5 H12_5 0.80(4) . ?
C13_5 O13_5 1.4098(18) . ?
C13_5 C14_5 1.526(2) . ?
C13_5 H13A_5 1.0000 . ?
O13_5 H13_5 0.77(3) . ?
C14_5 O14_5 1.2372(17) . ?
C14_5 O15_5 1.2809(19) . ?
O15_5 H11_2 1.34(2) . ?
O10_6 C11_6 1.263(2) . ?
C11_6 O11_6 1.2501(18) . ?
C11_6 C12_6 1.529(2) . ?
C12_6 O12_6 1.4180(18) . ?
C12_6 C13_6 1.523(2) . ?
C12_6 H12A_6 1.0000 . ?
O12_6 H12_6 0.90(3) . ?
C13_6 O13_6 1.421(2) . ?
C13_6 C14_6 1.534(2) . ?
C13_6 H13A_6 1.0000 . ?
O13_6 H13_6 0.92(3) . ?
C14_6 O14_6 1.246(2) . ?
C14_6 O15_6 1.261(2) . ?

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
C12_1 N11_1 C16_1 121.17(11) . . ?
C12_1 N11_1 O11_1 119.46(11) . . ?
C16_1 N11_1 O11_1 118.77(11) . . ?
N11_1 O11_1 H11_1 102.1(12) . . ?
N13_1 C12_1 N12_1 121.35(12) . . ?
N13_1 C12_1 N11_1 122.25(12) . . ?
N12_1 C12_1 N11_1 116.40(12) . . ?
C12_1 N12_1 H12A_1 120.5(14) . . ?
C12_1 N12_1 H12B_1 115.8(13) . . ?
H12A_1 N12_1 H12B_1 120.6(19) . . ?
C12_1 N13_1 C14_1 117.97(11) . . ?
N21_1 C14_1 N13_1 116.11(12) . . ?
N21_1 C14_1 C15_1 122.32(12) . . ?
N13_1 C14_1 C15_1 121.56(12) . . ?
C16_1 C15_1 C14_1 118.54(12) . . ?
C16_1 C15_1 H15_1 120.7 . . ?
C14_1 C15_1 H15_1 120.7 . . ?
N16_1 C16_1 N11_1 116.37(12) . . ?
N16_1 C16_1 C15_1 125.80(12) . . ?
N11_1 C16_1 C15_1 117.82(12) . . ?
C16_1 N16_1 H16A_1 115.9(13) . . ?
C16_1 N16_1 H16B_1 117.8(16) . . ?
H16A_1 N16_1 H16B_1 122(2) . . ?
C14_1 N21_1 C22_1 119.94(12) . . ?
C14_1 N21_1 C26_1 119.28(12) . . ?
C22_1 N21_1 C26_1 117.11(12) . . ?
N21_1 C22_1 C23_1 112.81(13) . . ?
N21_1 C22_1 H22A_1 109.0 . . ?
C23_1 C22_1 H22A_1 109.0 . . ?
N21_1 C22_1 H22B_1 109.0 . . ?
C23_1 C22_1 H22B_1 109.0 . . ?
H22A_1 C22_1 H22B_1 107.8 . . ?
C24_1 C23_1 C22_1 110.75(15) . . ?
C24_1 C23_1 H23A_1 109.5 . . ?
C22_1 C23_1 H23A_1 109.5 . . ?
C24_1 C23_1 H23B_1 109.5 . . ?
C22_1 C23_1 H23B_1 109.5 . . ?
H23A_1 C23_1 H23B_1 108.1 . . ?
C23_1 C24_1 C25_1 108.32(14) . . ?
C23_1 C24_1 H24A_1 110.0 . . ?
C25_1 C24_1 H24A_1 110.0 . . ?
C23_1 C24_1 H24B_1 110.0 . . ?
C25_1 C24_1 H24B_1 110.0 . . ?
H24A_1 C24_1 H24B_1 108.4 . . ?
C24_1 C25_1 C26_1 110.97(14) . . ?
C24_1 C25_1 H25A_1 109.4 . . ?
C26_1 C25_1 H25A_1 109.4 . . ?
C24_1 C25_1 H25B_1 109.4 . . ?
C26_1 C25_1 H25B_1 109.4 . . ?
H25A_1 C25_1 H25B_1 108.0 . . ?
N21_1 C26_1 C25_1 112.02(14) . . ?
N21_1 C26_1 H26A_1 109.2 . . ?
C25_1 C26_1 H26A_1 109.2 . . ?
N21_1 C26_1 H26B_1 109.2 . . ?
C25_1 C26_1 H26B_1 109.2 . . ?
H26A_1 C26_1 H26B_1 107.9 . . ?
C12_2 N11_2 C16_2 121.19(12) . . ?
C12_2 N11_2 O11_2 119.38(12) . . ?
C16_2 N11_2 O11_2 119.36(12) . . ?
N11_2 O11_2 H11_2 106.6(11) . . ?
N13_2 C12_2 N12_2 120.73(14) . . ?
N13_2 C12_2 N11_2 121.63(13) . . ?
N12_2 C12_2 N11_2 117.60(13) . . ?
C12_2 N12_2 H12A_2 120.3(14) . . ?
C12_2 N12_2 H12B_2 122.6(15) . . ?
H12A_2 N12_2 H12B_2 114(2) . . ?
C12_2 N13_2 C14_2 118.80(13) . . ?
N21_2 C14_2 N13_2 115.91(13) . . ?
N21_2 C14_2 C15_2 122.29(13) . . ?
N13_2 C14_2 C15_2 121.80(13) . . ?
C16_2 C15_2 C14_2 118.41(13) . . ?
C16_2 C15_2 H15_2 120.8 . . ?
C14_2 C15_2 H15_2 120.8 . . ?
N16_2 C16_2 N11_2 116.67(13) . . ?
N16_2 C16_2 C15_2 125.35(14) . . ?
N11_2 C16_2 C15_2 117.98(14) . . ?
C16_2 N16_2 H16B_2 119.6(15) . . ?
C16_2 N16_2 H16A_2 118.9(13) . . ?
H16B_2 N16_2 H16A_2 111(2) . . ?
C14_2 N21_2 C22_2 122.97(14) . . ?
C14_2 N21_2 C26_2 121.66(13) . . ?
C22_2 N21_2 C26_2 114.02(13) . . ?
N21_2 C22_2 C23_2 111.16(16) . . ?
N21_2 C22_2 H22A_2 109.4 . . ?
C23_2 C22_2 H22A_2 109.4 . . ?
N21_2 C22_2 H22B_2 109.4 . . ?
C23_2 C22_2 H22B_2 109.4 . . ?
H22A_2 C22_2 H22B_2 108.0 . . ?
C22_2 C23_2 C24_2 111.66(15) . . ?
C22_2 C23_2 H23A_2 109.3 . . ?
C24_2 C23_2 H23A_2 109.3 . . ?
C22_2 C23_2 H23B_2 109.3 . . ?
C24_2 C23_2 H23B_2 109.3 . . ?
H23A_2 C23_2 H23B_2 107.9 . . ?
C25_2 C24_2 C23_2 110.03(14) . . ?
C25_2 C24_2 H24A_2 109.7 . . ?
C23_2 C24_2 H24A_2 109.7 . . ?
C25_2 C24_2 H24B_2 109.7 . . ?
C23_2 C24_2 H24B_2 109.7 . . ?
H24A_2 C24_2 H24B_2 108.2 . . ?
C26_2 C25_2 C24_2 111.27(17) . . ?
C26_2 C25_2 H25A_2 109.4 . . ?
C24_2 C25_2 H25A_2 109.4 . . ?
C26_2 C25_2 H25B_2 109.4 . . ?
C24_2 C25_2 H25B_2 109.4 . . ?
H25A_2 C25_2 H25B_2 108.0 . . ?
N21_2 C26_2 C25_2 110.56(14) . . ?
N21_2 C26_2 H26A_2 109.5 . . ?
C25_2 C26_2 H26A_2 109.5 . . ?
N21_2 C26_2 H26B_2 109.5 . . ?
C25_2 C26_2 H26B_2 109.5 . . ?
H26A_2 C26_2 H26B_2 108.1 . . ?
C12_3 N11_3 C16_3 120.98(12) . . ?
C12_3 N11_3 O11_3 119.35(11) . . ?
C16_3 N11_3 O11_3 118.28(11) . . ?
N11_3 O11_3 H11_3 106.4(13) . . ?
N13_3 C12_3 N12_3 121.05(14) . . ?
N13_3 C12_3 N11_3 122.28(13) . . ?
N12_3 C12_3 N11_3 116.67(13) . . ?
C12_3 N12_3 H12A_3 120.3(15) . . ?
C12_3 N12_3 H12B_3 118.9(18) . . ?
H12A_3 N12_3 H12B_3 121(2) . . ?
C12_3 N13_3 C14_3 118.27(12) . . ?
N21_3 C14_3 N13_3 115.72(13) . . ?
N21_3 C14_3 C15_3 122.41(13) . . ?
N13_3 C14_3 C15_3 121.86(12) . . ?
C16_3 C15_3 C14_3 118.24(12) . . ?
C16_3 C15_3 H15_3 120.9 . . ?
C14_3 C15_3 H15_3 120.9 . . ?
N16_3 C16_3 N11_3 116.52(12) . . ?
N16_3 C16_3 C15_3 125.42(13) . . ?
N11_3 C16_3 C15_3 118.06(13) . . ?
C16_3 N16_3 H16B_3 118.3(15) . . ?
C16_3 N16_3 H16A_3 115.2(15) . . ?
H16B_3 N16_3 H16A_3 126(2) . . ?
C14_3 N21_3 C22_3 123.71(13) . . ?
C14_3 N21_3 C26_3 122.26(13) . . ?
C22_3 N21_3 C26_3 113.74(12) . . ?
N21_3 C22_3 C23_3 110.46(15) . . ?
N21_3 C22_3 H22A_3 109.6 . . ?
C23_3 C22_3 H22A_3 109.6 . . ?
N21_3 C22_3 H22B_3 109.6 . . ?
C23_3 C22_3 H22B_3 109.6 . . ?
H22A_3 C22_3 H22B_3 108.1 . . ?
C22_3 C23_3 C24_3 110.66(15) . . ?
C22_3 C23_3 H23A_3 109.5 . . ?
C24_3 C23_3 H23A_3 109.5 . . ?
C22_3 C23_3 H23B_3 109.5 . . ?
C24_3 C23_3 H23B_3 109.5 . . ?
H23A_3 C23_3 H23B_3 108.1 . . ?
C25_3 C24_3 C23_3 109.98(14) . . ?
C25_3 C24_3 H24A_3 109.7 . . ?
C23_3 C24_3 H24A_3 109.7 . . ?
C25_3 C24_3 H24B_3 109.7 . . ?
C23_3 C24_3 H24B_3 109.7 . . ?
H24A_3 C24_3 H24B_3 108.2 . . ?
C24_3 C25_3 C26_3 110.97(16) . . ?
C24_3 C25_3 H25A_3 109.4 . . ?
C26_3 C25_3 H25A_3 109.4 . . ?
C24_3 C25_3 H25B_3 109.4 . . ?
C26_3 C25_3 H25B_3 109.4 . . ?
H25A_3 C25_3 H25B_3 108.0 . . ?
N21_3 C26_3 C25_3 110.38(14) . . ?
N21_3 C26_3 H26A_3 109.6 . . ?
C25_3 C26_3 H26A_3 109.6 . . ?
N21_3 C26_3 H26B_3 109.6 . . ?
C25_3 C26_3 H26B_3 109.6 . . ?
H26A_3 C26_3 H26B_3 108.1 . . ?
C16_4 N11_4 C12_4 120.19(13) . . ?
C16_4 N11_4 O11_4 117.36(12) . . ?
C12_4 N11_4 O11_4 119.64(12) . . ?
N11_4 O11_4 H11_4 113.6(17) . . ?
N13_4 C12_4 N12_4 121.29(14) . . ?
N13_4 C12_4 N11_4 121.90(13) . . ?
N12_4 C12_4 N11_4 116.80(15) . . ?
C12_4 N12_4 H12A_4 116.6(18) . . ?
C12_4 N12_4 H12B_4 116.9(18) . . ?
H12A_4 N12_4 H12B_4 120(3) . . ?
C12_4 N13_4 C14_4 118.55(13) . . ?
N21_4 C14_4 N13_4 116.48(13) . . ?
N21_4 C14_4 C15_4 121.82(13) . . ?
N13_4 C14_4 C15_4 121.69(13) . . ?
C16_4 C15_4 C14_4 118.51(12) . . ?
C16_4 C15_4 H15_4 120.7 . . ?
C14_4 C15_4 H15_4 120.7 . . ?
N16_4 C16_4 N11_4 117.31(13) . . ?
N16_4 C16_4 C15_4 123.85(13) . . ?
N11_4 C16_4 C15_4 118.83(12) . . ?
C16_4 N16_4 H16A_4 123.0(14) . . ?
C16_4 N16_4 H16B_4 121.0(16) . . ?
H16A_4 N16_4 H16B_4 113(2) . . ?
C14_4 N21_4 C26_4 122.05(14) . . ?
C14_4 N21_4 C22_4 120.55(13) . . ?
C26_4 N21_4 C22_4 115.13(14) . . ?
N21_4 C22_4 C23_4 111.66(15) . . ?
N21_4 C22_4 H22A_4 109.3 . . ?
C23_4 C22_4 H22A_4 109.3 . . ?
N21_4 C22_4 H22B_4 109.3 . . ?
C23_4 C22_4 H22B_4 109.3 . . ?
H22A_4 C22_4 H22B_4 107.9 . . ?
C24_4 C23_4 C22_4 110.9(2) . . ?
C24_4 C23_4 H23A_4 109.5 . . ?
C22_4 C23_4 H23A_4 109.5 . . ?
C24_4 C23_4 H23B_4 109.5 . . ?
C22_4 C23_4 H23B_4 109.5 . . ?
H23A_4 C23_4 H23B_4 108.0 . . ?
C23_4 C24_4 C25_4 109.58(17) . . ?
C23_4 C24_4 H24A_4 109.8 . . ?
C25_4 C24_4 H24A_4 109.8 . . ?
C23_4 C24_4 H24B_4 109.8 . . ?
C25_4 C24_4 H24B_4 109.8 . . ?
H24A_4 C24_4 H24B_4 108.2 . . ?
C26_4 C25_4 C24_4 111.55(17) . . ?
C26_4 C25_4 H25A_4 109.3 . . ?
C24_4 C25_4 H25A_4 109.3 . . ?
C26_4 C25_4 H25B_4 109.3 . . ?
C24_4 C25_4 H25B_4 109.3 . . ?
H25A_4 C25_4 H25B_4 108.0 . . ?
N21_4 C26_4 C25_4 110.30(17) . . ?
N21_4 C26_4 H26A_4 109.6 . . ?
C25_4 C26_4 H26A_4 109.6 . . ?
N21_4 C26_4 H26B_4 109.6 . . ?
C25_4 C26_4 H26B_4 109.6 . . ?
H26A_4 C26_4 H26B_4 108.1 . . ?
C11_5 O10_5 H11_1 105.4(8) . . ?
O11_5 C11_5 O10_5 125.95(15) . . ?
O11_5 C11_5 C12_5 118.45(13) . . ?
O10_5 C11_5 C12_5 115.59(13) . . ?
O12_5 C12_5 C11_5 110.82(14) . . ?
O12_5 C12_5 C13_5 110.43(12) . . ?
C11_5 C12_5 C13_5 109.85(12) . . ?
O12_5 C12_5 H12A_5 108.6 . . ?
C11_5 C12_5 H12A_5 108.6 . . ?
C13_5 C12_5 H12A_5 108.6 . . ?
C12_5 O12_5 H12_5 106(2) . . ?
O13_5 C13_5 C14_5 112.22(11) . . ?
O13_5 C13_5 C12_5 108.81(12) . . ?
C14_5 C13_5 C12_5 108.39(11) . . ?
O13_5 C13_5 H13A_5 109.1 . . ?
C14_5 C13_5 H13A_5 109.1 . . ?
C12_5 C13_5 H13A_5 109.1 . . ?
C13_5 O13_5 H13_5 109.5(18) . . ?
O14_5 C14_5 O15_5 124.73(14) . . ?
O14_5 C14_5 C13_5 120.74(13) . . ?
O15_5 C14_5 C13_5 114.53(12) . . ?
C14_5 O15_5 H11_2 115.2(10) . . ?
O11_6 C11_6 O10_6 126.39(14) . . ?
O11_6 C11_6 C12_6 117.56(14) . . ?
O10_6 C11_6 C12_6 116.04(13) . . ?
O12_6 C12_6 C13_6 109.96(12) . . ?
O12_6 C12_6 C11_6 112.79(13) . . ?
C13_6 C12_6 C11_6 111.32(11) . . ?
O12_6 C12_6 H12A_6 107.5 . . ?
C13_6 C12_6 H12A_6 107.5 . . ?
C11_6 C12_6 H12A_6 107.5 . . ?
C12_6 O12_6 H12_6 109.8(15) . . ?
O13_6 C13_6 C12_6 109.67(15) . . ?
O13_6 C13_6 C14_6 109.79(14) . . ?
C12_6 C13_6 C14_6 110.00(12) . . ?
O13_6 C13_6 H13A_6 109.1 . . ?
C12_6 C13_6 H13A_6 109.1 . . ?
C14_6 C13_6 H13A_6 109.1 . . ?
C13_6 O13_6 H13_6 102(2) . . ?
O14_6 C14_6 O15_6 125.31(15) . . ?
O14_6 C14_6 C13_6 116.89(15) . . ?
O15_6 C14_6 C13_6 117.78(14) . . ?

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
C16_1 N11_1 C12_1 N13_1 6.9(2) . . . . ?
O11_1 N11_1 C12_1 N13_1 178.01(13) . . . . ?
C16_1 N11_1 C12_1 N12_1 -172.73(14) . . . . ?
O11_1 N11_1 C12_1 N12_1 -1.7(2) . . . . ?
N12_1 C12_1 N13_1 C14_1 179.04(14) . . . . ?
N11_1 C12_1 N13_1 C14_1 -0.6(2) . . . . ?
C12_1 N13_1 C14_1 N21_1 172.59(14) . . . . ?
C12_1 N13_1 C14_1 C15_1 -6.6(2) . . . . ?
N21_1 C14_1 C15_1 C16_1 -171.63(14) . . . . ?
N13_1 C14_1 C15_1 C16_1 7.5(2) . . . . ?
C12_1 N11_1 C16_1 N16_1 173.53(14) . . . . ?
O11_1 N11_1 C16_1 N16_1 2.40(19) . . . . ?
C12_1 N11_1 C16_1 C15_1 -5.8(2) . . . . ?
O11_1 N11_1 C16_1 C15_1 -176.89(12) . . . . ?
C14_1 C15_1 C16_1 N16_1 179.56(15) . . . . ?
C14_1 C15_1 C16_1 N11_1 -1.2(2) . . . . ?
N13_1 C14_1 N21_1 C22_1 16.5(2) . . . . ?
C15_1 C14_1 N21_1 C22_1 -164.36(14) . . . . ?
N13_1 C14_1 N21_1 C26_1 174.25(13) . . . . ?
C15_1 C14_1 N21_1 C26_1 -6.6(2) . . . . ?
C14_1 N21_1 C22_1 C23_1 -156.65(15) . . . . ?
C26_1 N21_1 C22_1 C23_1 45.1(2) . . . . ?
N21_1 C22_1 C23_1 C24_1 -52.02(19) . . . . ?
C22_1 C23_1 C24_1 C25_1 59.80(19) . . . . ?
C23_1 C24_1 C25_1 C26_1 -60.3(2) . . . . ?
C14_1 N21_1 C26_1 C25_1 156.56(14) . . . . ?
C22_1 N21_1 C26_1 C25_1 -45.03(19) . . . . ?
C24_1 C25_1 C26_1 N21_1 52.29(19) . . . . ?
C16_2 N11_2 C12_2 N13_2 -3.4(2) . . . . ?
O11_2 N11_2 C12_2 N13_2 173.27(13) . . . . ?
C16_2 N11_2 C12_2 N12_2 174.09(13) . . . . ?
O11_2 N11_2 C12_2 N12_2 -9.2(2) . . . . ?
N12_2 C12_2 N13_2 C14_2 -177.46(14) . . . . ?
N11_2 C12_2 N13_2 C14_2 0.0(2) . . . . ?
C12_2 N13_2 C14_2 N21_2 -176.10(14) . . . . ?
C12_2 N13_2 C14_2 C15_2 3.9(2) . . . . ?
N21_2 C14_2 C15_2 C16_2 175.66(15) . . . . ?
N13_2 C14_2 C15_2 C16_2 -4.4(2) . . . . ?
C12_2 N11_2 C16_2 N16_2 -178.01(13) . . . . ?
O11_2 N11_2 C16_2 N16_2 5.3(2) . . . . ?
C12_2 N11_2 C16_2 C15_2 2.9(2) . . . . ?
O11_2 N11_2 C16_2 C15_2 -173.85(13) . . . . ?
C14_2 C15_2 C16_2 N16_2 -178.13(15) . . . . ?
C14_2 C15_2 C16_2 N11_2 0.9(2) . . . . ?
N13_2 C14_2 N21_2 C22_2 -174.79(17) . . . . ?
C15_2 C14_2 N21_2 C22_2 5.2(3) . . . . ?
N13_2 C14_2 N21_2 C26_2 -8.8(2) . . . . ?
C15_2 C14_2 N21_2 C26_2 171.13(16) . . . . ?
C14_2 N21_2 C22_2 C23_2 -137.99(17) . . . . ?
C26_2 N21_2 C22_2 C23_2 55.1(2) . . . . ?
N21_2 C22_2 C23_2 C24_2 -53.0(2) . . . . ?
C22_2 C23_2 C24_2 C25_2 53.4(2) . . . . ?
C23_2 C24_2 C25_2 C26_2 -54.9(2) . . . . ?
C14_2 N21_2 C26_2 C25_2 136.38(17) . . . . ?
C22_2 N21_2 C26_2 C25_2 -56.5(2) . . . . ?
C24_2 C25_2 C26_2 N21_2 55.9(2) . . . . ?
C16_3 N11_3 C12_3 N13_3 -6.1(2) . . . . ?
O11_3 N11_3 C12_3 N13_3 -172.44(13) . . . . ?
C16_3 N11_3 C12_3 N12_3 174.97(14) . . . . ?
O11_3 N11_3 C12_3 N12_3 8.6(2) . . . . ?
N12_3 C12_3 N13_3 C14_3 -179.18(15) . . . . ?
N11_3 C12_3 N13_3 C14_3 1.9(2) . . . . ?
C12_3 N13_3 C14_3 N21_3 -179.02(14) . . . . ?
C12_3 N13_3 C14_3 C15_3 1.7(2) . . . . ?
N21_3 C14_3 C15_3 C16_3 179.56(15) . . . . ?
N13_3 C14_3 C15_3 C16_3 -1.2(2) . . . . ?
C12_3 N11_3 C16_3 N16_3 -173.81(13) . . . . ?
O11_3 N11_3 C16_3 N16_3 -7.32(19) . . . . ?
C12_3 N11_3 C16_3 C15_3 6.4(2) . . . . ?
O11_3 N11_3 C16_3 C15_3 172.85(12) . . . . ?
C14_3 C15_3 C16_3 N16_3 177.38(14) . . . . ?
C14_3 C15_3 C16_3 N11_3 -2.8(2) . . . . ?
N13_3 C14_3 N21_3 C22_3 177.22(16) . . . . ?
C15_3 C14_3 N21_3 C22_3 -3.5(3) . . . . ?
N13_3 C14_3 N21_3 C26_3 3.8(2) . . . . ?
C15_3 C14_3 N21_3 C26_3 -176.92(15) . . . . ?
C14_3 N21_3 C22_3 C23_3 128.64(17) . . . . ?
C26_3 N21_3 C22_3 C23_3 -57.42(19) . . . . ?
N21_3 C22_3 C23_3 C24_3 55.39(19) . . . . ?
C22_3 C23_3 C24_3 C25_3 -55.0(2) . . . . ?
C23_3 C24_3 C25_3 C26_3 55.1(2) . . . . ?
C14_3 N21_3 C26_3 C25_3 -128.62(16) . . . . ?
C22_3 N21_3 C26_3 C25_3 57.34(19) . . . . ?
C24_3 C25_3 C26_3 N21_3 -55.55(18) . . . . ?
C16_4 N11_4 C12_4 N13_4 -6.9(2) . . . . ?
O11_4 N11_4 C12_4 N13_4 -167.45(15) . . . . ?
C16_4 N11_4 C12_4 N12_4 172.97(15) . . . . ?
O11_4 N11_4 C12_4 N12_4 12.4(2) . . . . ?
N12_4 C12_4 N13_4 C14_4 -176.55(17) . . . . ?
N11_4 C12_4 N13_4 C14_4 3.3(2) . . . . ?
C12_4 N13_4 C14_4 N21_4 -177.87(16) . . . . ?
C12_4 N13_4 C14_4 C15_4 0.8(2) . . . . ?
N21_4 C14_4 C15_4 C16_4 177.21(15) . . . . ?
N13_4 C14_4 C15_4 C16_4 -1.4(2) . . . . ?
C12_4 N11_4 C16_4 N16_4 -172.57(15) . . . . ?
O11_4 N11_4 C16_4 N16_4 -11.6(2) . . . . ?
C12_4 N11_4 C16_4 C15_4 6.1(2) . . . . ?
O11_4 N11_4 C16_4 C15_4 167.06(13) . . . . ?
C14_4 C15_4 C16_4 N16_4 176.51(15) . . . . ?
C14_4 C15_4 C16_4 N11_4 -2.1(2) . . . . ?
N13_4 C14_4 N21_4 C26_4 178.39(16) . . . . ?
C15_4 C14_4 N21_4 C26_4 -0.3(3) . . . . ?
N13_4 C14_4 N21_4 C22_4 -19.6(2) . . . . ?
C15_4 C14_4 N21_4 C22_4 161.75(17) . . . . ?
C14_4 N21_4 C22_4 C23_4 142.88(19) . . . . ?
C26_4 N21_4 C22_4 C23_4 -53.9(2) . . . . ?
N21_4 C22_4 C23_4 C24_4 54.0(2) . . . . ?
C22_4 C23_4 C24_4 C25_4 -55.4(3) . . . . ?
C23_4 C24_4 C25_4 C26_4 56.2(3) . . . . ?
C14_4 N21_4 C26_4 C25_4 -143.44(17) . . . . ?
C22_4 N21_4 C26_4 C25_4 53.6(2) . . . . ?
C24_4 C25_4 C26_4 N21_4 -54.3(2) . . . . ?
O11_5 C11_5 C12_5 O12_5 -0.9(2) . . . . ?
O10_5 C11_5 C12_5 O12_5 178.21(14) . . . . ?
O11_5 C11_5 C12_5 C13_5 -123.18(15) . . . . ?
O10_5 C11_5 C12_5 C13_5 55.92(18) . . . . ?
O12_5 C12_5 C13_5 O13_5 -63.66(17) . . . . ?
C11_5 C12_5 C13_5 O13_5 58.86(16) . . . . ?
O12_5 C12_5 C13_5 C14_5 58.64(17) . . . . ?
C11_5 C12_5 C13_5 C14_5 -178.84(12) . . . . ?
O13_5 C13_5 C14_5 O14_5 6.72(17) . . . . ?
C12_5 C13_5 C14_5 O14_5 -113.47(14) . . . . ?
O13_5 C13_5 C14_5 O15_5 -174.06(12) . . . . ?
C12_5 C13_5 C14_5 O15_5 65.75(15) . . . . ?
O11_6 C11_6 C12_6 O12_6 -178.07(12) . . . . ?
O10_6 C11_6 C12_6 O12_6 0.88(17) . . . . ?
O11_6 C11_6 C12_6 C13_6 57.77(18) . . . . ?
O10_6 C11_6 C12_6 C13_6 -123.28(15) . . . . ?
O12_6 C12_6 C13_6 O13_6 -75.95(17) . . . . ?
C11_6 C12_6 C13_6 O13_6 49.80(18) . . . . ?
O12_6 C12_6 C13_6 C14_6 44.89(19) . . . . ?
C11_6 C12_6 C13_6 C14_6 170.64(14) . . . . ?
O13_6 C13_6 C14_6 O14_6 -15.0(2) . . . . ?
C12_6 C13_6 C14_6 O14_6 -135.75(17) . . . . ?
O13_6 C13_6 C14_6 O15_6 163.76(15) . . . . ?
C12_6 C13_6 C14_6 O15_6 43.0(2) . . . . ?

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
O11_1 H11_1 O10_5 1.08(2) 1.40(2) 2.4665(16) 168.1(19) .
O11_2 H11_2 O15_5 1.13(2) 1.34(2) 2.4539(17) 170(2) .
O11_3 H11_3 O10_6 0.95(3) 1.59(2) 2.5337(16) 172(2) .
O11_4 H11_4 O15_6 0.88(3) 1.66(3) 2.5310(17) 169(2) .
O12_5 H12_5 O11_5 0.80(4) 2.14(3) 2.6300(19) 120(3) .
O12_6 H12_6 O11_2 0.90(3) 2.18(3) 2.9512(17) 145(2) 1_565
O13_5 H13_5 O12_6 0.77(3) 1.99(3) 2.7591(18) 172(3) .
O13_6 H13_6 O14_6 0.92(3) 1.97(4) 2.608(2) 125(3) .
N12_1 H12A_1 N13_1 0.90(2) 2.15(2) 3.0375(17) 167(2) 2_655
N12_2 H12A_2 O11_5 0.92(3) 2.10(3) 2.991(2) 165(2) 1_545
N12_3 H12A_3 O15_6 0.91(3) 2.05(3) 2.930(2) 160(2) 1_565
N12_4 H12A_4 O1S 0.84(3) 2.11(3) 2.935(3) 168(2) .
N12_1 H12B_1 O11_5 0.94(2) 2.25(2) 3.1056(18) 151(2) .
N12_2 H12B_2 O10_6 0.86(2) 2.29(2) 3.1271(18) 167(2) 1_545
N12_3 H12B_3 O15_5 0.78(3) 2.22(2) 2.9275(18) 152(2) 1_565
N12_4 H12B_4 O14_6 0.84(3) 2.18(3) 2.892(2) 143(3) .
N16_1 H16A_1 O11_6 0.96(2) 2.10(2) 2.9118(16) 141.4(17) .
N16_2 H16A_2 O11_6 0.92(2) 2.21(2) 3.0796(19) 157(2) 3_445
N16_3 H16A_3 O13_5 0.86(2) 1.97(2) 2.8279(18) 179(3) 3
N16_4 H16A_4 O11_4 0.92(2) 2.37(2) 2.6311(17) 96.3(16) .
N16_1 H16B_1 O14_5 0.80(2) 2.07(2) 2.8501(16) 166(2) 3
N16_4 H16B_4 O11_6 0.83(2) 2.07(2) 2.8844(17) 169(2) 3_445

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.200
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.060


# Attachment '_3__cif1.cif'

data_171504s
_database_code_depnum_ccdc_archive 'CCDC 733877'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

?

;

_chemical_name_common            ?

_chemical_melting_point          ?

_chemical_formula_moiety         'C22 H38 N10 O8'

_chemical_formula_sum            'C22 H38 N10 O8'

_chemical_formula_weight         570.62

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'
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'

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   C2/c

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.2840(8)

_cell_length_b                   10.4088(4)

_cell_length_c                   13.8485(5)

_cell_angle_alpha                90.00

_cell_angle_beta                 117.311(2)

_cell_angle_gamma                90.00

_cell_volume                     2726.01(18)

_cell_formula_units_Z            4

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    4102

_cell_measurement_theta_min      4.25

_cell_measurement_theta_max      64.54

_exptl_crystal_description       rod

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.33

_exptl_crystal_size_mid          0.12

_exptl_crystal_size_min          0.11

_exptl_crystal_density_meas      ?

_exptl_crystal_density_diffrn    1.390

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             1216

_exptl_absorpt_coefficient_mu    0.905

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.7545

_exptl_absorpt_correction_T_max  0.9070

_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      173(2)

_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         0

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            11094

_diffrn_reflns_av_R_equivalents  0.0345

_diffrn_reflns_av_sigmaI/netI    0.0223

_diffrn_reflns_limit_h_min       -23

_diffrn_reflns_limit_h_max       24

_diffrn_reflns_limit_k_min       -12

_diffrn_reflns_limit_k_max       12

_diffrn_reflns_limit_l_min       -16

_diffrn_reflns_limit_l_max       15

_diffrn_reflns_theta_min         4.68

_diffrn_reflns_theta_max         65.10

_reflns_number_total             2200

_reflns_number_gt                1843

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+4.5728P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2200

_refine_ls_number_parameters     207

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0572

_refine_ls_R_factor_gt           0.0476

_refine_ls_wR_factor_ref         0.1327

_refine_ls_wR_factor_gt          0.1248

_refine_ls_goodness_of_fit_ref   1.051

_refine_ls_restrained_S_all      1.051

_refine_ls_shift/su_max          0.000

_refine_ls_shift/su_mean         0.000

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

C1 C 0.07394(11) 0.9222(2) 0.22724(18) 0.0276(5) Uani 1 1 d . . .
C2 C 0.10770(11) 0.7587(2) 0.35962(18) 0.0273(5) Uani 1 1 d . . .
C3 C 0.08850(11) 0.6666(2) 0.28131(16) 0.0221(5) Uani 1 1 d . . .
H3 H 0.0929 0.5782 0.3005 0.026 Uiso 1 1 calc R . .
C4 C 0.06347(11) 0.7015(2) 0.17734(19) 0.0285(5) Uani 1 1 d . . .
C5 C 0.14605(14) 0.5863(3) 0.4959(2) 0.0387(6) Uani 1 1 d . . .
H5A H 0.1428 0.5335 0.4343 0.046 Uiso 1 1 calc R . .
H5B H 0.1072 0.5601 0.5122 0.046 Uiso 1 1 calc R . .
C6 C 0.21613(15) 0.5614(3) 0.5941(2) 0.0502(7) Uani 1 1 d . . .
H6A H 0.2183 0.4706 0.6167 0.060 Uiso 1 1 calc R . .
H6B H 0.2549 0.5759 0.5747 0.060 Uiso 1 1 calc R . .
C7 C 0.22637(17) 0.6478(4) 0.6873(2) 0.0622(9) Uani 1 1 d . . .
H7A H 0.2741 0.6342 0.7485 0.075 Uiso 1 1 calc R . .
H7B H 0.1911 0.6264 0.7128 0.075 Uiso 1 1 calc R . .
C8 C 0.21806(15) 0.7864(3) 0.6519(2) 0.0565(9) Uani 1 1 d . . .
H8A H 0.2570 0.8101 0.6351 0.068 Uiso 1 1 calc R . .
H8B H 0.2216 0.8417 0.7124 0.068 Uiso 1 1 calc R . .
C9 C 0.14794(14) 0.8107(3) 0.5529(2) 0.0406(6) Uani 1 1 d . . .
H9A H 0.1090 0.7999 0.5726 0.049 Uiso 1 1 calc R . .
H9B H 0.1466 0.9002 0.5278 0.049 Uiso 1 1 calc R . .
N1 N 0.06108(9) 0.82840(18) 0.15111(14) 0.0263(4) Uani 1 1 d . . .
N2 N 0.09737(11) 0.8879(2) 0.33273(17) 0.0389(5) Uani 1 1 d . . .
N3 N 0.13762(11) 0.72158(19) 0.46474(15) 0.0325(5) Uani 1 1 d . . .
N4 N 0.04135(12) 0.6180(2) 0.09554(19) 0.0368(5) Uani 1 1 d . . .
N5 N 0.06346(12) 1.0427(2) 0.1915(2) 0.0364(5) Uani 1 1 d . . .
O1 O 0.03810(8) 0.86309(15) 0.04340(12) 0.0280(4) Uani 1 1 d . . .
C1G C 0.14930(12) 0.7737(2) 0.94767(18) 0.0289(5) Uani 1 1 d . . .
C2G C 0.22000(12) 0.7396(2) 0.95672(18) 0.0304(5) Uani 1 1 d . . .
H2G H 0.2214 0.7005 0.8958 0.036 Uiso 1 1 calc R . .
O1G O 0.09550(8) 0.74620(17) 0.86078(13) 0.0353(4) Uani 1 1 d . . .
O2G O 0.14823(9) 0.82936(19) 1.02791(14) 0.0401(5) Uani 1 1 d . . .
O1W O 0.02756(10) 0.35363(16) 0.14807(14) 0.0346(4) Uani 1 1 d . . .
H1W H 0.0587(18) 0.343(3) 0.217(3) 0.060 Uiso 1 1 d . . .
H2W H -0.0126(19) 0.321(3) 0.145(3) 0.057 Uiso 1 1 d . . .
H3N H 0.0431(15) 1.053(3) 0.118(3) 0.042(8) Uiso 1 1 d . . .
H4N H 0.0708(14) 1.102(3) 0.236(2) 0.037(8) Uiso 1 1 d . . .
H1N H 0.0368(16) 0.537(3) 0.111(2) 0.052(9) Uiso 1 1 d . . .
H2N H 0.0201(16) 0.649(3) 0.024(3) 0.048(8) Uiso 1 1 d . . .
H1O H 0.0840(17) 0.844(3) 0.034(3) 0.063(9) Uiso 1 1 d . . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

;

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

C1 N5 1.329(3) . ?
C1 N2 1.357(3) . ?
C1 N1 1.369(3) . ?
C2 N3 1.350(3) . ?
C2 C3 1.362(3) . ?
C2 N2 1.385(3) . ?
C3 C4 1.336(3) . ?
C3 H3 0.9500 . ?
C4 N4 1.331(3) . ?
C4 N1 1.365(3) . ?
C5 N3 1.460(3) . ?
C5 C6 1.510(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.506(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.508(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.467(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N1 O1 1.388(2) . ?
N4 H1N 0.89(3) . ?
N4 H2N 0.94(3) . ?
N5 H3N 0.91(3) . ?
N5 H4N 0.84(3) . ?
O1 H1O 1.06(3) . ?
C1G O1G 1.256(3) . ?
C1G O2G 1.263(3) . ?
C1G C2G 1.494(3) . ?
C2G C2G 1.308(5) 7_567 ?
C2G H2G 0.9500 . ?
O1W H1W 0.89(4) . ?
O1W H2W 0.90(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

N5 C1 N2 124.4(2) . . ?
N5 C1 N1 116.5(2) . . ?
N2 C1 N1 119.1(2) . . ?
N3 C2 C3 118.5(2) . . ?
N3 C2 N2 120.4(2) . . ?
C3 C2 N2 121.1(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
N4 C4 C3 123.4(2) . . ?
N4 C4 N1 116.8(2) . . ?
C3 C4 N1 119.9(2) . . ?
N3 C5 C6 111.6(2) . . ?
N3 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 111.4(2) . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 110.1(3) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C7 C8 C9 112.0(3) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C9 C8 110.9(2) . . ?
N3 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C4 N1 C1 121.01(19) . . ?
C4 N1 O1 119.33(18) . . ?
C1 N1 O1 119.32(18) . . ?
C1 N2 C2 118.6(2) . . ?
C2 N3 C5 121.9(2) . . ?
C2 N3 C9 122.2(2) . . ?
C5 N3 C9 114.4(2) . . ?
C4 N4 H1N 117(2) . . ?
C4 N4 H2N 119.0(18) . . ?
H1N N4 H2N 122(3) . . ?
C1 N5 H3N 116.3(18) . . ?
C1 N5 H4N 118.8(19) . . ?
H3N N5 H4N 124(3) . . ?
N1 O1 H1O 101.2(17) . . ?
O1G C1G O2G 124.8(2) . . ?
O1G C1G C2G 117.8(2) . . ?
O2G C1G C2G 117.3(2) . . ?
C2G C2G C1G 124.1(3) 7_567 . ?
C2G C2G H2G 118.0 7_567 . ?
C1G C2G H2G 118.0 . . ?
H1W O1W H2W 104(3) . . ?

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

N3 C2 C3 C4 -175.3(2) . . . . ?
N2 C2 C3 C4 4.3(3) . . . . ?
C2 C3 C4 N4 -177.7(2) . . . . ?
C2 C3 C4 N1 3.7(3) . . . . ?
N3 C5 C6 C7 54.1(3) . . . . ?
C5 C6 C7 C8 -54.9(3) . . . . ?
C6 C7 C8 C9 55.0(3) . . . . ?
C7 C8 C9 N3 -53.4(3) . . . . ?
N4 C4 N1 C1 171.5(2) . . . . ?
C3 C4 N1 C1 -9.8(3) . . . . ?
N4 C4 N1 O1 -1.7(3) . . . . ?
C3 C4 N1 O1 176.99(18) . . . . ?
N5 C1 N1 C4 -173.5(2) . . . . ?
N2 C1 N1 C4 7.7(3) . . . . ?
N5 C1 N1 O1 -0.3(3) . . . . ?
N2 C1 N1 O1 -179.07(18) . . . . ?
N5 C1 N2 C2 -178.4(2) . . . . ?
N1 C1 N2 C2 0.2(3) . . . . ?
N3 C2 N2 C1 173.3(2) . . . . ?
C3 C2 N2 C1 -6.3(3) . . . . ?
C3 C2 N3 C5 -3.6(3) . . . . ?
N2 C2 N3 C5 176.8(2) . . . . ?
C3 C2 N3 C9 -168.5(2) . . . . ?
N2 C2 N3 C9 11.9(3) . . . . ?
C6 C5 N3 C2 140.4(2) . . . . ?
C6 C5 N3 C9 -53.6(3) . . . . ?
C8 C9 N3 C2 -141.1(3) . . . . ?
C8 C9 N3 C5 53.0(3) . . . . ?
O1G C1G C2G C2G -178.5(3) . . . 7_567 ?
O2G C1G C2G C2G 2.2(4) . . . 7_567 ?

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

O1W H1W O1G 0.89(4) 2.00(4) 2.818(2) 152(3) 6_565
O1W H2W O1G 0.90(4) 1.87(4) 2.768(2) 179(3) 5_566
N5 H3N O1 0.91(3) 2.28(3) 3.124(3) 154(2) 5_575
N5 H4N O1G 0.84(3) 2.22(3) 3.054(3) 177(3) 6_575
N4 H1N O1W 0.89(3) 2.01(4) 2.895(3) 179(3) .
N4 H2N O1W 0.94(3) 2.12(3) 3.013(3) 159(3) 5_565
O1 H1O O2G 1.06(3) 1.41(3) 2.475(2) 174(3) 1_554

_diffrn_measured_fraction_theta_max 0.944

_diffrn_reflns_theta_full        65.10

_diffrn_measured_fraction_theta_full 0.944

_refine_diff_density_max         0.495

_refine_diff_density_min         -0.486

_refine_diff_density_rms         0.053

# Attachment '_4__cif1.cif'

data_ns0806m
_database_code_depnum_ccdc_archive 'CCDC 733878'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3189-80-03 minoxidil and succinic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O)2 (C4 H6 O4) (H2 O)2
;
_chemical_formula_sum            'C22 H40 N10 O8'
_chemical_formula_weight         572.64

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   9.3818(4)
_cell_length_b                   10.4613(5)
_cell_length_c                   14.1476(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.410(3)
_cell_angle_gamma                90.00
_cell_volume                     1369.84(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6730
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      32.66

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12500
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         32.54
_reflns_number_total             4914
_reflns_number_gt                3969
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4914
_refine_ls_number_parameters     208
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1S O -0.05919(9) 0.14465(8) 0.62220(6) 0.02529(17) Uani 1 1 d . . .
H1A H 0.0233(18) 0.1805(16) 0.6520(12) 0.030 Uiso 1 1 d . . .
H1B H -0.1194(18) 0.1583(16) 0.6595(12) 0.030 Uiso 1 1 d . . .
O11 O 0.07894(7) 0.35841(7) 0.49588(5) 0.01884(15) Uani 1 1 d . . .
H11 H 0.1695(16) 0.3457(13) 0.5445(10) 0.023 Uiso 1 1 d . . .
N11 N 0.12387(9) 0.32732(8) 0.41074(6) 0.01765(16) Uani 1 1 d . A .
C12 C 0.12967(10) 0.20152(10) 0.38527(7) 0.02099(19) Uani 1 1 d . . .
N12 N 0.09022(12) 0.11569(10) 0.44599(7) 0.0281(2) Uani 1 1 d . A .
H12A H 0.0470(18) 0.1462(16) 0.4941(12) 0.034 Uiso 1 1 d . . .
H12B H 0.0845(19) 0.0375(17) 0.4272(12) 0.034 Uiso 1 1 d . . .
N13 N 0.17694(10) 0.16917(9) 0.30316(7) 0.0220(2) Uani 0.497(12) 1 d P A 1
C13 C 0.17694(10) 0.16917(9) 0.30316(7) 0.0220(2) Uani 0.503(12) 1 d P A 2
H13 H 0.1855 0.0820 0.2862 0.026 Uiso 0.503(12) 1 calc PR A 2
C14 C 0.21241(10) 0.26531(10) 0.24475(7) 0.01865(17) Uani 1 1 d . . .
C15 C 0.19262(10) 0.39215(9) 0.26553(6) 0.02043(19) Uani 0.497(12) 1 d P A 1
H15 H 0.2110 0.4574 0.2224 0.025 Uiso 0.497(12) 1 calc PR A 1
N15 N 0.19262(10) 0.39215(9) 0.26553(6) 0.02043(19) Uani 0.503(12) 1 d P A 2
C16 C 0.14661(10) 0.42192(10) 0.34836(6) 0.01870(18) Uani 1 1 d . . .
N16 N 0.12380(10) 0.54191(9) 0.37470(6) 0.02414(18) Uani 1 1 d . A .
H16A H 0.0834(17) 0.5552(15) 0.4256(11) 0.029 Uiso 1 1 d . . .
H16B H 0.1303(17) 0.6031(16) 0.3323(12) 0.029 Uiso 1 1 d . . .
N21 N 0.26743(11) 0.23457(9) 0.16535(6) 0.02414(18) Uani 1 1 d . A .
C22 C 0.29201(13) 0.10351(12) 0.13757(9) 0.0293(2) Uani 1 1 d . . .
H22A H 0.2188 0.0794 0.0818 0.035 Uiso 1 1 calc R A .
H22B H 0.2818 0.0451 0.1911 0.035 Uiso 1 1 calc R . .
C23 C 0.44299(16) 0.08989(18) 0.11175(11) 0.0455(4) Uani 1 1 d . A .
H23A H 0.5159 0.1031 0.1699 0.055 Uiso 1 1 calc R . .
H23B H 0.4551 0.0021 0.0881 0.055 Uiso 1 1 calc R . .
C24 C 0.46853(15) 0.1848(2) 0.03612(10) 0.0540(5) Uani 1 1 d . . .
H24A H 0.4037 0.1654 -0.0247 0.065 Uiso 1 1 calc R A .
H24B H 0.5696 0.1779 0.0247 0.065 Uiso 1 1 calc R . .
C25 C 0.44023(16) 0.31889(19) 0.06790(10) 0.0476(4) Uani 1 1 d . A .
H25A H 0.4505 0.3799 0.0160 0.057 Uiso 1 1 calc R . .
H25B H 0.5122 0.3416 0.1247 0.057 Uiso 1 1 calc R . .
C26 C 0.28883(15) 0.32876(14) 0.09269(9) 0.0341(3) Uani 1 1 d . . .
H26A H 0.2738 0.4157 0.1169 0.041 Uiso 1 1 calc R A .
H26B H 0.2168 0.3146 0.0342 0.041 Uiso 1 1 calc R . .
C31 C 0.29410(10) 0.29414(11) 0.69867(7) 0.0223(2) Uani 1 1 d . . .
O31 O 0.18173(8) 0.25574(9) 0.72672(6) 0.02804(18) Uani 1 1 d . . .
O32 O 0.29970(8) 0.33530(9) 0.61512(5) 0.02564(17) Uani 1 1 d . . .
C32A C 0.4327(3) 0.2846(6) 0.7717(2) 0.0280(7) Uani 0.685(15) 1 d PD . 1
H32A H 0.4364 0.3574 0.8167 0.034 Uiso 0.685(15) 1 calc PR . 1
H32B H 0.4296 0.2051 0.8092 0.034 Uiso 0.685(15) 1 calc PR . 1
C32B C 0.4328(8) 0.3243(11) 0.7663(6) 0.0280(7) Uani 0.315(15) 1 d PD . 2
H32C H 0.4207 0.4099 0.7938 0.034 Uiso 0.315(15) 1 calc PR . 2
H32D H 0.4404 0.2625 0.8199 0.034 Uiso 0.315(15) 1 calc PR . 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1S H1A 0.900(18) . ?
O1S H1B 0.846(17) . ?
O11 N11 1.3786(10) . ?
O11 H11 1.010(15) . ?
N11 C16 1.3658(12) . ?
N11 C12 1.3679(13) . ?
C12 N12 1.3361(15) . ?
C12 N13 1.3524(13) . ?
N12 H12A 0.905(17) . ?
N12 H12B 0.859(18) . ?
N13 C14 1.3766(14) . ?
C14 N21 1.3496(12) . ?
C14 C15 1.3782(13) . ?
C15 C16 1.3497(12) . ?
C15 H15 0.9500 . ?
C16 N16 1.3366(14) . ?
N16 H16A 0.877(16) . ?
N16 H16B 0.886(17) . ?
N21 C22 1.4551(14) . ?
N21 C26 1.4612(15) . ?
C22 C23 1.5262(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.507(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.510(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5213(19) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C31 O31 1.2519(12) . ?
C31 O32 1.2671(12) . ?
C31 C32B 1.517(9) . ?
C31 C32A 1.526(3) . ?
O32 H11 1.451(15) . ?
C32A C32A 1.492(5) 2_656 ?
C32A H32A 0.9900 . ?
C32A H32B 0.9900 . ?
C32B C32B 1.412(13) 2_656 ?
C32B H32C 0.9900 . ?
C32B H32D 0.9900 . ?

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
H1A O1S H1B 104.3(15) . . ?
N11 O11 H11 102.7(8) . . ?
C16 N11 C12 120.64(8) . . ?
C16 N11 O11 119.74(8) . . ?
C12 N11 O11 119.22(8) . . ?
N12 C12 N13 123.25(10) . . ?
N12 C12 N11 116.74(9) . . ?
N13 C12 N11 119.99(9) . . ?
C12 N12 H12A 116.8(11) . . ?
C12 N12 H12B 116.8(11) . . ?
H12A N12 H12B 123.8(15) . . ?
C12 N13 C14 118.57(9) . . ?
N21 C14 N13 119.24(9) . . ?
N21 C14 C15 119.35(9) . . ?
N13 C14 C15 121.41(8) . . ?
C16 C15 C14 118.73(9) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N16 C16 C15 123.18(9) . . ?
N16 C16 N11 116.82(8) . . ?
C15 C16 N11 119.99(9) . . ?
C16 N16 H16A 119.2(11) . . ?
C16 N16 H16B 117.2(10) . . ?
H16A N16 H16B 121.8(15) . . ?
C14 N21 C22 123.26(9) . . ?
C14 N21 C26 122.69(10) . . ?
C22 N21 C26 113.54(9) . . ?
N21 C22 C23 110.30(11) . . ?
N21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
N21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 111.71(12) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 C25 110.15(11) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 110.36(12) . . ?
C24 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
N21 C26 C25 110.93(11) . . ?
N21 C26 H26A 109.5 . . ?
C25 C26 H26A 109.5 . . ?
N21 C26 H26B 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.0 . . ?
O31 C31 O32 124.76(9) . . ?
O31 C31 C32B 123.1(3) . . ?
O32 C31 C32B 110.8(3) . . ?
O31 C31 C32A 115.65(17) . . ?
O32 C31 C32A 119.55(17) . . ?
C31 O32 H11 120.7(6) . . ?
C32A C32A C31 114.0(3) 2_656 . ?
C32A C32A H32A 108.8 2_656 . ?
C31 C32A H32A 108.8 . . ?
C32A C32A H32B 108.8 2_656 . ?
C31 C32A H32B 108.8 . . ?
H32A C32A H32B 107.6 . . ?
C32B C32B C31 120.9(9) 2_656 . ?
C32B C32B H32C 107.1 2_656 . ?
C31 C32B H32C 107.1 . . ?
C32B C32B H32D 107.1 2_656 . ?
C31 C32B H32D 107.1 . . ?
H32C C32B H32D 106.8 . . ?

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
C16 N11 C12 N12 -172.65(9) . . . . ?
O11 N11 C12 N12 0.13(13) . . . . ?
C16 N11 C12 N13 8.88(14) . . . . ?
O11 N11 C12 N13 -178.35(8) . . . . ?
N12 C12 N13 C14 178.82(10) . . . . ?
N11 C12 N13 C14 -2.81(14) . . . . ?
C12 N13 C14 N21 176.30(9) . . . . ?
C12 N13 C14 C15 -3.86(14) . . . . ?
N21 C14 C15 C16 -175.65(9) . . . . ?
N13 C14 C15 C16 4.51(14) . . . . ?
C14 C15 C16 N16 -179.77(9) . . . . ?
C14 C15 C16 N11 1.54(14) . . . . ?
C12 N11 C16 N16 173.01(9) . . . . ?
O11 N11 C16 N16 0.27(13) . . . . ?
C12 N11 C16 C15 -8.22(14) . . . . ?
O11 N11 C16 C15 179.04(8) . . . . ?
N13 C14 N21 C22 -0.10(15) . . . . ?
C15 C14 N21 C22 -179.95(10) . . . . ?
N13 C14 N21 C26 171.13(10) . . . . ?
C15 C14 N21 C26 -8.71(15) . . . . ?
C14 N21 C22 C23 -132.26(12) . . . . ?
C26 N21 C22 C23 55.78(14) . . . . ?
N21 C22 C23 C24 -54.46(15) . . . . ?
C22 C23 C24 C25 54.97(16) . . . . ?
C23 C24 C25 C26 -55.25(15) . . . . ?
C14 N21 C26 C25 130.81(12) . . . . ?
C22 N21 C26 C25 -57.18(14) . . . . ?
C24 C25 C26 N21 55.94(14) . . . . ?
O31 C31 C32A C32A 158.83(8) . . . 2_656 ?
O32 C31 C32A C32A -19.1(3) . . . 2_656 ?
O31 C31 C32B C32B 158.0(3) . . . 2_656 ?
O32 C31 C32B C32B -34.2(4) . . . 2_656 ?

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
O11 H11 O32 1.010(15) 1.451(15) 2.4599(10) 176.7(14) .
N12 H12A O1S 0.905(17) 2.207(17) 3.0683(13) 158.8(15) .
N12 H12B O1S 0.859(18) 2.030(18) 2.8881(13) 176.5(17) 3_556
N16 H16A O11 0.877(16) 2.219(16) 3.0326(11) 154.0(14) 3_566
N16 H16B O31 0.886(17) 2.209(17) 3.0873(13) 170.9(14) 4_565
O1S H1A O31 0.900(18) 1.853(18) 2.7483(11) 172.8(15) .
O1S H1B O31 0.846(17) 2.068(17) 2.8362(11) 150.6(15) 2_556

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.054

# Attachment '_5__cif1.cif'

data_ns0803m
_database_code_depnum_ccdc_archive 'CCDC 733879'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3189-76-02 minoxidil : adipic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O)2 (C6 H10 O4)
;
_chemical_formula_sum            'C24 H40 N10 O6'
_chemical_formula_weight         564.66

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.6780(5)
_cell_length_b                   17.9581(8)
_cell_length_c                   13.6730(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.615(2)
_cell_angle_gamma                90.00
_cell_volume                     2858.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            44461
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         31.51
_reflns_number_total             9224
_reflns_number_gt                6534
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9224
_refine_ls_number_parameters     443
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1459
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N11 N -0.07741(9) 0.34139(6) -0.09918(7) 0.0235(2) Uani 1 1 d . . .
O11 O -0.12468(8) 0.40043(5) -0.05129(7) 0.0268(2) Uani 1 1 d . . .
H11 H -0.0690(14) 0.4111(9) 0.0042(13) 0.032 Uiso 1 1 d . . .
N12 N 0.00210(10) 0.42729(6) -0.19928(8) 0.0288(2) Uani 1 1 d . . .
H12A H 0.0410 0.4391 -0.2496 0.035 Uiso 1 1 calc R . .
H12B H -0.0255 0.4626 -0.1633 0.035 Uiso 1 1 calc R . .
N13 N 0.02561(10) 0.30133(6) -0.23048(8) 0.0259(2) Uani 1 1 d . . .
C14 C 0.00355(10) 0.22914(7) -0.20559(9) 0.0231(2) Uani 1 1 d . . .
C16 C -0.10148(11) 0.26983(7) -0.07334(9) 0.0241(2) Uani 1 1 d . . .
C15 C -0.06234(11) 0.21253(7) -0.12719(9) 0.0231(2) Uani 1 1 d . . .
H15 H -0.0795 0.1624 -0.1118 0.028 Uiso 1 1 calc R . .
N16 N -0.16265(10) 0.26108(7) 0.00478(8) 0.0300(2) Uani 1 1 d . . .
H16A H -0.1800 0.2161 0.0243 0.036 Uiso 1 1 calc R . .
H16B H -0.1854 0.3003 0.0365 0.036 Uiso 1 1 calc R . .
C12 C -0.01491(11) 0.35607(7) -0.17764(9) 0.0230(2) Uani 1 1 d . . .
N21 N 0.04976(10) 0.17576(6) -0.25907(9) 0.0310(3) Uani 1 1 d . . .
C22 C 0.02454(15) 0.09681(8) -0.25170(11) 0.0374(3) Uani 1 1 d . . .
H22A H -0.0210 0.0879 -0.1948 0.045 Uiso 1 1 calc R . .
H22B H 0.0972 0.0684 -0.2413 0.045 Uiso 1 1 calc R . .
C23 C -0.04271(15) 0.07003(8) -0.34524(12) 0.0399(4) Uani 1 1 d . . .
H23A H -0.0540 0.0155 -0.3416 0.048 Uiso 1 1 calc R . .
H23B H -0.1194 0.0939 -0.3510 0.048 Uiso 1 1 calc R . .
C24 C 0.01987(14) 0.08858(8) -0.43516(11) 0.0374(3) Uani 1 1 d . . .
H24A H -0.0296 0.0757 -0.4950 0.045 Uiso 1 1 calc R . .
H24B H 0.0908 0.0583 -0.4347 0.045 Uiso 1 1 calc R . .
C25 C 0.05083(13) 0.17074(8) -0.43766(11) 0.0353(3) Uani 1 1 d . . .
H25A H 0.0981 0.1803 -0.4932 0.042 Uiso 1 1 calc R . .
H25B H -0.0202 0.2008 -0.4478 0.042 Uiso 1 1 calc R . .
C26 C 0.11710(13) 0.19371(9) -0.34228(11) 0.0389(4) Uani 1 1 d . . .
H26A H 0.1916 0.1671 -0.3351 0.047 Uiso 1 1 calc R . .
H26B H 0.1328 0.2479 -0.3433 0.047 Uiso 1 1 calc R . .
N31A N 0.30108(19) 0.36302(16) 0.88292(19) 0.0174(4) Uani 0.123(13) 1 d PD A 1
O31A O 0.3324(10) 0.4251(5) 0.8301(6) 0.0245(9) Uani 0.123(13) 1 d PD A 1
H31A H 0.2809(15) 0.4318(9) 0.7761(13) 0.029 Uiso 0.123(13) 1 d P A 1
C32A C 0.325(2) 0.2929(3) 0.8511(11) 0.0235(14) Uani 0.123(13) 1 d PD A 1
N32A N 0.3872(4) 0.2883(4) 0.7730(3) 0.0249(7) Uani 0.123(13) 1 d PD A 1
H32A H 0.4034 0.2445 0.7489 0.030 Uiso 0.123(13) 1 calc PR A 1
H32B H 0.4118 0.3291 0.7459 0.030 Uiso 0.123(13) 1 calc PR A 1
N33A N 0.2840(2) 0.2324(3) 0.8974(3) 0.0223(7) Uani 0.123(13) 1 d PD A 1
C34A C 0.21929(16) 0.24353(11) 0.97733(13) 0.0214(4) Uani 0.123(13) 1 d PD A 1
C35A C 0.19180(15) 0.31327(12) 1.00714(14) 0.0225(4) Uani 0.123(13) 1 d PD A 1
H35A H 0.1454 0.3199 1.0604 0.027 Uiso 0.123(13) 1 d PR A 1
C36A C 0.236(2) 0.3731(4) 0.9608(11) 0.0264(12) Uani 0.123(13) 1 d PD A 1
N36A N 0.2150(8) 0.4430(4) 0.9877(7) 0.0273(10) Uani 0.123(13) 1 d PD A 1
H36A H 0.2426 0.4805 0.9556 0.033 Uiso 0.123(13) 1 calc PR A 1
H36B H 0.1735 0.4514 1.0375 0.033 Uiso 0.123(13) 1 calc PR A 1
N41A N 0.18080(15) 0.18538(9) 1.02808(12) 0.0299(3) Uani 0.123(13) 1 d P A 1
C42A C 0.2172(4) 0.1091(2) 1.0173(3) 0.0437(8) Uani 0.123(13) 1 d P A 1
H42A H 0.2651 0.1049 0.9610 0.052 Uiso 0.123(13) 1 calc PR A 1
H42B H 0.1492 0.0765 1.0045 0.052 Uiso 0.123(13) 1 calc PR A 1
C43A C 0.2868(3) 0.08429(14) 1.11195(19) 0.0514(7) Uani 0.123(13) 1 d P A 1
H43A H 0.3106 0.0317 1.1057 0.062 Uiso 0.123(13) 1 calc PR A 1
H43B H 0.3569 0.1152 1.1226 0.062 Uiso 0.123(13) 1 calc PR A 1
C44A C 0.2143(2) 0.09239(14) 1.19927(18) 0.0444(5) Uani 0.123(13) 1 d P A 1
H44A H 0.1478 0.0581 1.1914 0.053 Uiso 0.123(13) 1 calc PR A 1
H44B H 0.2609 0.0789 1.2604 0.053 Uiso 0.123(13) 1 calc PR A 1
C45A C 0.17221(19) 0.17192(14) 1.20632(16) 0.0358(5) Uani 0.123(13) 1 d P A 1
H45A H 0.2384 0.2056 1.2213 0.043 Uiso 0.123(13) 1 calc PR A 1
H45B H 0.1208 0.1760 1.2602 0.043 Uiso 0.123(13) 1 calc PR A 1
C46A C 0.10756(17) 0.19512(12) 1.10974(15) 0.0333(4) Uani 0.123(13) 1 d P A 1
H46A H 0.0373 0.1645 1.0979 0.040 Uiso 0.123(13) 1 calc PR A 1
H46B H 0.0841 0.2479 1.1136 0.040 Uiso 0.123(13) 1 calc PR A 1
N31B N 0.30108(19) 0.36302(16) 0.88292(19) 0.0174(4) Uani 0.577(13) 1 d PD A 2
O31B O 0.3324(10) 0.4251(5) 0.8301(6) 0.0245(9) Uani 0.577(13) 1 d PD A 2
H31B H 0.2809(15) 0.4318(9) 0.7761(13) 0.029 Uiso 0.577(13) 1 d P A 2
C32B C 0.236(2) 0.3731(4) 0.9608(11) 0.0264(12) Uani 0.577(13) 1 d PD A 2
N32B N 0.2150(8) 0.4430(4) 0.9877(7) 0.0273(10) Uani 0.577(13) 1 d PD A 2
H32C H 0.2426 0.4805 0.9556 0.033 Uiso 0.577(13) 1 calc PR A 2
H32D H 0.1735 0.4514 1.0375 0.033 Uiso 0.577(13) 1 calc PR A 2
N33B N 0.19180(15) 0.31327(12) 1.00714(14) 0.0225(4) Uani 0.577(13) 1 d PD A 2
C34B C 0.21929(16) 0.24353(11) 0.97733(13) 0.0214(4) Uani 0.577(13) 1 d PD A 2
C35B C 0.2840(2) 0.2324(3) 0.8974(3) 0.0223(7) Uani 0.577(13) 1 d PD A 2
H35B H 0.3027 0.1827 0.8773 0.027 Uiso 0.577(13) 1 d PR A 2
C36B C 0.325(2) 0.2929(3) 0.8511(11) 0.0235(14) Uani 0.577(13) 1 d PD A 2
N36B N 0.3872(4) 0.2883(4) 0.7730(3) 0.0249(7) Uani 0.577(13) 1 d PD A 2
H36C H 0.4034 0.2445 0.7489 0.030 Uiso 0.577(13) 1 calc PR A 2
H36D H 0.4118 0.3291 0.7459 0.030 Uiso 0.577(13) 1 calc PR A 2
N41B N 0.18080(15) 0.18538(9) 1.02808(12) 0.0299(3) Uani 0.577(13) 1 d P A 2
C42B C 0.2172(4) 0.1091(2) 1.0173(3) 0.0437(8) Uani 0.577(13) 1 d P A 2
H42C H 0.2651 0.1049 0.9610 0.052 Uiso 0.577(13) 1 calc PR A 2
H42D H 0.1492 0.0765 1.0045 0.052 Uiso 0.577(13) 1 calc PR A 2
C43B C 0.2868(3) 0.08429(14) 1.11195(19) 0.0514(7) Uani 0.577(13) 1 d P A 2
H43C H 0.3106 0.0317 1.1057 0.062 Uiso 0.577(13) 1 calc PR A 2
H43D H 0.3569 0.1152 1.1226 0.062 Uiso 0.577(13) 1 calc PR A 2
C44B C 0.2143(2) 0.09239(14) 1.19927(18) 0.0444(5) Uani 0.577(13) 1 d P A 2
H44C H 0.1478 0.0581 1.1914 0.053 Uiso 0.577(13) 1 calc PR A 2
H44D H 0.2609 0.0789 1.2604 0.053 Uiso 0.577(13) 1 calc PR A 2
C45B C 0.17221(19) 0.17192(14) 1.20632(16) 0.0358(5) Uani 0.577(13) 1 d P A 2
H45C H 0.2384 0.2056 1.2213 0.043 Uiso 0.577(13) 1 calc PR A 2
H45D H 0.1208 0.1760 1.2602 0.043 Uiso 0.577(13) 1 calc PR A 2
C46B C 0.10756(17) 0.19512(12) 1.10974(15) 0.0333(4) Uani 0.577(13) 1 d P A 2
H46C H 0.0373 0.1645 1.0979 0.040 Uiso 0.577(13) 1 calc PR A 2
H46D H 0.0841 0.2479 1.1136 0.040 Uiso 0.577(13) 1 calc PR A 2
N31C N 0.2786(6) 0.3606(4) 0.8719(5) 0.0174(4) Uani 0.30 1 d PD B 3
O31C O 0.340(2) 0.4225(12) 0.8421(17) 0.0245(9) Uani 0.30 1 d PD B 3
H31C H 0.2809(15) 0.4318(9) 0.7761(13) 0.029 Uiso 0.30 1 d P C 3
C32C C 0.318(5) 0.2919(8) 0.846(3) 0.0235(14) Uani 0.30 1 d PD B 3
N32C N 0.3677(12) 0.2877(11) 0.7619(9) 0.0249(7) Uani 0.30 1 d PD B 3
H32E H 0.3978 0.2453 0.7440 0.030 Uiso 0.30 1 calc PR B 3
H32F H 0.3704 0.3272 0.7241 0.030 Uiso 0.30 1 calc PR B 3
N33C N 0.3124(7) 0.2319(6) 0.9063(6) 0.0223(7) Uani 0.30 1 d PD B 3
C34C C 0.2655(4) 0.2419(3) 0.9932(3) 0.0214(4) Uani 0.30 1 d PD B 3
C35C C 0.2286(5) 0.3118(4) 1.0239(5) 0.0225(4) Uani 0.30 1 d PD B 3
H35C H 0.2035 0.3187 1.0877 0.027 Uiso 0.30 1 calc PR B 3
C36C C 0.230(5) 0.3693(9) 0.959(3) 0.0264(12) Uani 0.30 1 d PD B 3
N36C N 0.201(2) 0.4390(9) 0.9797(18) 0.0273(10) Uani 0.30 1 d PD B 3
H36E H 0.1787 0.4502 1.0380 0.033 Uiso 0.30 1 calc PR B 3
H36F H 0.2031 0.4739 0.9347 0.033 Uiso 0.30 1 calc PR B 3
N41C N 0.2640(4) 0.1801(2) 1.0501(3) 0.0299(3) Uani 0.30 1 d P B 3
C42C C 0.2633(7) 0.1050(4) 1.0089(7) 0.0356(17) Uani 0.30 1 d P B 3
H42E H 0.3217 0.0742 1.0467 0.043 Uiso 0.30 1 calc PR B 3
H42F H 0.2839 0.1073 0.9402 0.043 Uiso 0.30 1 calc PR B 3
C43C C 0.1485(6) 0.0696(3) 1.0118(4) 0.0446(13) Uani 0.30 1 d P B 3
H43E H 0.1527 0.0174 0.9889 0.054 Uiso 0.30 1 calc PR B 3
H43F H 0.0924 0.0963 0.9663 0.054 Uiso 0.30 1 calc PR B 3
C44C C 0.1068(5) 0.0704(3) 1.1140(5) 0.0452(13) Uani 0.30 1 d P B 3
H44E H 0.1554 0.0369 1.1573 0.054 Uiso 0.30 1 calc PR B 3
H44F H 0.0269 0.0518 1.1113 0.054 Uiso 0.30 1 calc PR B 3
C45C C 0.1117(5) 0.1497(3) 1.1570(4) 0.0402(12) Uani 0.30 1 d P B 3
H45E H 0.0542 0.1816 1.1201 0.048 Uiso 0.30 1 calc PR B 3
H45F H 0.0933 0.1483 1.2264 0.048 Uiso 0.30 1 calc PR B 3
C46C C 0.2312(4) 0.1819(3) 1.1504(3) 0.0321(9) Uani 0.30 1 d P B 3
H46E H 0.2327 0.2339 1.1742 0.039 Uiso 0.30 1 calc PR B 3
H46F H 0.2873 0.1529 1.1931 0.039 Uiso 0.30 1 calc PR B 3
C51 C -0.00600(11) 0.38902(7) 0.16914(9) 0.0240(2) Uani 1 1 d . . .
O50 O 0.00992(8) 0.43054(5) 0.09486(6) 0.0291(2) Uani 1 1 d . . .
O51 O -0.09474(9) 0.35217(6) 0.17630(7) 0.0325(2) Uani 1 1 d . . .
C52 C 0.09011(12) 0.38624(9) 0.24980(10) 0.0345(3) Uani 1 1 d . . .
H52A H 0.1471 0.4252 0.2373 0.041 Uiso 1 1 calc R . .
H52B H 0.1291 0.3374 0.2473 0.041 Uiso 1 1 calc R . .
C53 C 0.05134(11) 0.39740(7) 0.35241(9) 0.0266(3) Uani 1 1 d . . .
H53A H 0.0193 0.4482 0.3575 0.032 Uiso 1 1 calc R . .
H53B H -0.0104 0.3613 0.3634 0.032 Uiso 1 1 calc R . .
C54 C 0.14923(13) 0.38713(8) 0.43124(10) 0.0329(3) Uani 1 1 d . . .
H54A H 0.1717 0.3340 0.4337 0.040 Uiso 1 1 calc R . .
H54B H 0.2163 0.4162 0.4131 0.040 Uiso 1 1 calc R . .
C55 C 0.11936(12) 0.41106(8) 0.53191(9) 0.0308(3) Uani 1 1 d . . .
H55A H 0.0591 0.3773 0.5531 0.037 Uiso 1 1 calc R . .
H55B H 0.0861 0.4617 0.5267 0.037 Uiso 1 1 calc R . .
C56 C 0.21789(11) 0.41176(7) 0.61071(9) 0.0251(2) Uani 1 1 d . . .
O56 O 0.19752(8) 0.44603(5) 0.69011(6) 0.0287(2) Uani 1 1 d . . .
O57 O 0.31028(8) 0.38052(6) 0.59791(7) 0.0313(2) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N11 C16 1.3678(16) . ?
N11 C12 1.3709(15) . ?
N11 O11 1.3841(13) . ?
O11 H11 0.977(17) . ?
N12 C12 1.3313(16) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 C12 1.3294(15) . ?
N13 C14 1.3700(16) . ?
C14 N21 1.3447(16) . ?
C14 C15 1.4011(16) . ?
C16 N16 1.3411(15) . ?
C16 C15 1.3654(17) . ?
C15 H15 0.9500 . ?
N16 H16A 0.8800 . ?
N16 H16B 0.8800 . ?
N21 C22 1.4533(19) . ?
N21 C26 1.4700(18) . ?
C22 C23 1.524(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.517(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.520(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.519(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
N31A C36A 1.369(6) . ?
N31A C32A 1.369(5) . ?
N31A O31A 1.393(5) . ?
O31A H31A 0.92(2) . ?
O31A H31B 0.92(2) . ?
O31A H31C 0.92(2) . ?
C32A N32A 1.340(6) . ?
C32A N33A 1.365(8) . ?
N32A H32A 0.8800 . ?
N32A H32B 0.8800 . ?
N33A C34A 1.392(4) . ?
N33A H35B 0.9639 . ?
C34A N41A 1.351(2) . ?
C34A C35A 1.363(3) . ?
C35A C36A 1.370(8) . ?
C35A H35A 0.9497 . ?
C36A N36A 1.335(5) . ?
N36A H36A 0.8800 . ?
N36A H36B 0.8800 . ?
N41A C42A 1.446(4) . ?
N41A C46A 1.470(2) . ?
C42A C43A 1.538(5) . ?
C42A H42A 0.9900 . ?
C42A H42B 0.9900 . ?
C43A C44A 1.525(4) . ?
C43A H43A 0.9900 . ?
C43A H43B 0.9900 . ?
C44A C45A 1.516(3) . ?
C44A H44A 0.9900 . ?
C44A H44B 0.9900 . ?
C45A C46A 1.525(3) . ?
C45A H45A 0.9900 . ?
C45A H45B 0.9900 . ?
C46A H46A 0.9900 . ?
C46A H46B 0.9900 . ?
N31C C32C 1.373(12) . ?
N31C C36C 1.375(12) . ?
N31C O31C 1.403(12) . ?
O31C H31A 1.11(3) . ?
O31C H31B 1.11(3) . ?
O31C H31C 1.11(3) . ?
C32C N32C 1.332(12) . ?
C32C N33C 1.360(14) . ?
N32C H32E 0.8800 . ?
N32C H32F 0.8800 . ?
N33C C34C 1.359(9) . ?
N33C H35B 0.9714 . ?
C34C N41C 1.357(6) . ?
C34C C35C 1.403(8) . ?
C35C C36C 1.359(15) . ?
C35C H35A 1.1362 . ?
C35C H35C 0.9500 . ?
C36C N36C 1.334(12) . ?
N36C H36E 0.8800 . ?
N36C H36F 0.8800 . ?
N41C C46C 1.453(6) . ?
N41C C42C 1.462(9) . ?
C42C C43C 1.487(10) . ?
C42C H42E 0.9900 . ?
C42C H42F 0.9900 . ?
C43C C44C 1.516(8) . ?
C43C H43E 0.9900 . ?
C43C H43F 0.9900 . ?
C44C C45C 1.539(8) . ?
C44C H44E 0.9900 . ?
C44C H44F 0.9900 . ?
C45C C46C 1.519(8) . ?
C45C H45E 0.9900 . ?
C45C H45F 0.9900 . ?
C46C H46E 0.9900 . ?
C46C H46F 0.9900 . ?
C51 O51 1.2400(15) . ?
C51 O50 1.2854(15) . ?
C51 C52 1.5098(19) . ?
C52 C53 1.5217(17) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.5180(19) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.5094(18) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 C56 1.5118(19) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C56 O57 1.2409(16) . ?
C56 O56 1.2866(15) . ?

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
C16 N11 C12 121.08(10) . . ?
C16 N11 O11 119.96(9) . . ?
C12 N11 O11 118.72(10) . . ?
N11 O11 H11 104.5(10) . . ?
C12 N12 H12A 120.0 . . ?
C12 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
C12 N13 C14 118.85(10) . . ?
N21 C14 N13 116.60(11) . . ?
N21 C14 C15 122.23(12) . . ?
N13 C14 C15 121.16(11) . . ?
N16 C16 C15 124.34(12) . . ?
N16 C16 N11 116.71(11) . . ?
C15 C16 N11 118.95(11) . . ?
C16 C15 C14 118.71(11) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C16 N16 H16A 120.0 . . ?
C16 N16 H16B 120.0 . . ?
H16A N16 H16B 120.0 . . ?
N13 C12 N12 121.58(11) . . ?
N13 C12 N11 121.22(11) . . ?
N12 C12 N11 117.20(11) . . ?
C14 N21 C22 124.43(12) . . ?
C14 N21 C26 121.85(12) . . ?
C22 N21 C26 113.05(11) . . ?
N21 C22 C23 110.08(12) . . ?
N21 C22 H22A 109.6 . . ?
C23 C22 H22A 109.6 . . ?
N21 C22 H22B 109.6 . . ?
C23 C22 H22B 109.6 . . ?
H22A C22 H22B 108.2 . . ?
C24 C23 C22 111.20(13) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 111.24(12) . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 110.49(14) . . ?
C26 C25 H25A 109.6 . . ?
C24 C25 H25A 109.6 . . ?
C26 C25 H25B 109.6 . . ?
C24 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
N21 C26 C25 109.74(11) . . ?
N21 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
N21 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
C36A N31A C32A 120.7(5) . . ?
C36A N31A O31A 118.9(6) . . ?
C32A N31A O31A 120.1(5) . . ?
N31A O31A H31A 109.9(12) . . ?
N31A O31A H31B 109.9(12) . . ?
N31A O31A H31C 109.9(12) . . ?
N32A C32A N33A 123.7(6) . . ?
N32A C32A N31A 116.6(6) . . ?
N33A C32A N31A 119.7(5) . . ?
C32A N32A H32A 120.0 . . ?
C32A N32A H32B 120.0 . . ?
H32A N32A H32B 120.0 . . ?
C32A N33A C34A 119.0(4) . . ?
C32A N33A H35B 120.4 . . ?
C34A N33A H35B 120.5 . . ?
N41A C34A C35A 117.43(17) . . ?
N41A C34A N33A 121.1(2) . . ?
C35A C34A N33A 121.5(2) . . ?
C34A C35A C36A 118.4(3) . . ?
C34A C35A H35A 120.4 . . ?
C36A C35A H35A 121.1 . . ?
N36A C36A N31A 117.7(7) . . ?
N36A C36A C35A 121.7(6) . . ?
N31A C36A C35A 120.6(5) . . ?
C36A N36A H36A 120.0 . . ?
C36A N36A H36B 120.0 . . ?
H36A N36A H36B 120.0 . . ?
C34A N41A C42A 124.6(2) . . ?
C34A N41A C46A 122.42(16) . . ?
C42A N41A C46A 112.59(19) . . ?
N41A C42A C43A 109.2(3) . . ?
N41A C42A H42A 109.8 . . ?
C43A C42A H42A 109.8 . . ?
N41A C42A H42B 109.8 . . ?
C43A C42A H42B 109.8 . . ?
H42A C42A H42B 108.3 . . ?
C44A C43A C42A 110.0(2) . . ?
C44A C43A H43A 109.7 . . ?
C42A C43A H43A 109.7 . . ?
C44A C43A H43B 109.7 . . ?
C42A C43A H43B 109.7 . . ?
H43A C43A H43B 108.2 . . ?
C45A C44A C43A 110.06(18) . . ?
C45A C44A H44A 109.6 . . ?
C43A C44A H44A 109.6 . . ?
C45A C44A H44B 109.6 . . ?
C43A C44A H44B 109.6 . . ?
H44A C44A H44B 108.2 . . ?
C44A C45A C46A 110.0(2) . . ?
C44A C45A H45A 109.7 . . ?
C46A C45A H45A 109.7 . . ?
C44A C45A H45B 109.7 . . ?
C46A C45A H45B 109.7 . . ?
H45A C45A H45B 108.2 . . ?
N41A C46A C45A 110.32(16) . . ?
N41A C46A H46A 109.6 . . ?
C45A C46A H46A 109.6 . . ?
N41A C46A H46B 109.6 . . ?
C45A C46A H46B 109.6 . . ?
H46A C46A H46B 108.1 . . ?
C32C N31C C36C 119.7(9) . . ?
C32C N31C O31C 116.5(18) . . ?
C36C N31C O31C 114.9(18) . . ?
N31C O31C H31A 93.1(17) . . ?
N31C O31C H31B 93.1(17) . . ?
N31C O31C H31C 93.1(17) . . ?
N32C C32C N33C 121.6(14) . . ?
N32C C32C N31C 116.8(13) . . ?
N33C C32C N31C 121.5(11) . . ?
C32C N32C H32E 120.0 . . ?
C32C N32C H32F 120.0 . . ?
H32E N32C H32F 120.0 . . ?
C34C N33C C32C 117.9(9) . . ?
C34C N33C H35B 115.8 . . ?
C32C N33C H35B 118.9 . . ?
N41C C34C N33C 114.7(6) . . ?
N41C C34C C35C 122.8(5) . . ?
N33C C34C C35C 122.4(6) . . ?
C36C C35C C34C 117.7(8) . . ?
C36C C35C H35A 104.1 . . ?
C34C C35C H35A 122.7 . . ?
C36C C35C H35C 121.1 . . ?
C34C C35C H35C 121.2 . . ?
N36C C36C C35C 124.2(17) . . ?
N36C C36C N31C 114.7(14) . . ?
C35C C36C N31C 120.4(12) . . ?
C36C N36C H36E 120.0 . . ?
C36C N36C H36F 120.0 . . ?
H36E N36C H36F 120.0 . . ?
C34C N41C C46C 122.7(4) . . ?
C34C N41C C42C 122.3(5) . . ?
C46C N41C C42C 113.0(4) . . ?
N41C C42C C43C 111.2(5) . . ?
N41C C42C H42E 109.4 . . ?
C43C C42C H42E 109.4 . . ?
N41C C42C H42F 109.4 . . ?
C43C C42C H42F 109.4 . . ?
H42E C42C H42F 108.0 . . ?
C42C C43C C44C 112.1(5) . . ?
C42C C43C H43E 109.2 . . ?
C44C C43C H43E 109.2 . . ?
C42C C43C H43F 109.2 . . ?
C44C C43C H43F 109.2 . . ?
H43E C43C H43F 107.9 . . ?
C43C C44C C45C 110.9(5) . . ?
C43C C44C H44E 109.5 . . ?
C45C C44C H44E 109.5 . . ?
C43C C44C H44F 109.5 . . ?
C45C C44C H44F 109.5 . . ?
H44E C44C H44F 108.0 . . ?
C46C C45C C44C 109.6(4) . . ?
C46C C45C H45E 109.8 . . ?
C44C C45C H45E 109.8 . . ?
C46C C45C H45F 109.8 . . ?
C44C C45C H45F 109.8 . . ?
H45E C45C H45F 108.2 . . ?
N41C C46C C45C 111.2(4) . . ?
N41C C46C H46E 109.4 . . ?
C45C C46C H46E 109.4 . . ?
N41C C46C H46F 109.4 . . ?
C45C C46C H46F 109.4 . . ?
H46E C46C H46F 108.0 . . ?
O51 C51 O50 123.15(12) . . ?
O51 C51 C52 120.11(12) . . ?
O50 C51 C52 116.75(12) . . ?
C51 C52 C53 114.22(11) . . ?
C51 C52 H52A 108.7 . . ?
C53 C52 H52A 108.7 . . ?
C51 C52 H52B 108.7 . . ?
C53 C52 H52B 108.7 . . ?
H52A C52 H52B 107.6 . . ?
C54 C53 C52 112.07(11) . . ?
C54 C53 H53A 109.2 . . ?
C52 C53 H53A 109.2 . . ?
C54 C53 H53B 109.2 . . ?
C52 C53 H53B 109.2 . . ?
H53A C53 H53B 107.9 . . ?
C55 C54 C53 113.38(11) . . ?
C55 C54 H54A 108.9 . . ?
C53 C54 H54A 108.9 . . ?
C55 C54 H54B 108.9 . . ?
C53 C54 H54B 108.9 . . ?
H54A C54 H54B 107.7 . . ?
C54 C55 C56 115.71(11) . . ?
C54 C55 H55A 108.4 . . ?
C56 C55 H55A 108.4 . . ?
C54 C55 H55B 108.4 . . ?
C56 C55 H55B 108.4 . . ?
H55A C55 H55B 107.4 . . ?
O57 C56 O56 123.85(13) . . ?
O57 C56 C55 121.08(11) . . ?
O56 C56 C55 115.06(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
C12 N13 C14 N21 -177.72(12) . . . . ?
C12 N13 C14 C15 1.25(19) . . . . ?
C12 N11 C16 N16 179.66(12) . . . . ?
O11 N11 C16 N16 -5.99(18) . . . . ?
C12 N11 C16 C15 -0.11(19) . . . . ?
O11 N11 C16 C15 174.24(11) . . . . ?
N16 C16 C15 C14 -178.20(12) . . . . ?
N11 C16 C15 C14 1.55(19) . . . . ?
N21 C14 C15 C16 176.75(12) . . . . ?
N13 C14 C15 C16 -2.16(19) . . . . ?
C14 N13 C12 N12 -178.86(12) . . . . ?
C14 N13 C12 N11 0.26(19) . . . . ?
C16 N11 C12 N13 -0.84(19) . . . . ?
O11 N11 C12 N13 -175.26(11) . . . . ?
C16 N11 C12 N12 178.32(12) . . . . ?
O11 N11 C12 N12 3.90(18) . . . . ?
N13 C14 N21 C22 -172.07(13) . . . . ?
C15 C14 N21 C22 9.0(2) . . . . ?
N13 C14 N21 C26 -2.13(19) . . . . ?
C15 C14 N21 C26 178.92(13) . . . . ?
C14 N21 C22 C23 111.58(16) . . . . ?
C26 N21 C22 C23 -59.15(17) . . . . ?
N21 C22 C23 C24 54.54(17) . . . . ?
C22 C23 C24 C25 -52.76(18) . . . . ?
C23 C24 C25 C26 53.64(17) . . . . ?
C14 N21 C26 C25 -110.74(15) . . . . ?
C22 N21 C26 C25 60.25(17) . . . . ?
C24 C25 C26 N21 -56.13(16) . . . . ?
C36A N31A C32A N32A 178.5(15) . . . . ?
O31A N31A C32A N32A 5(3) . . . . ?
C36A N31A C32A N33A 0(3) . . . . ?
O31A N31A C32A N33A -173.2(14) . . . . ?
N32A C32A N33A C34A -179.3(16) . . . . ?
N31A C32A N33A C34A -1(3) . . . . ?
C32A N33A C34A N41A -177.1(13) . . . . ?
C32A N33A C34A C35A 3.2(13) . . . . ?
N41A C34A C35A C36A 175.8(14) . . . . ?
N33A C34A C35A C36A -4.5(14) . . . . ?
C32A N31A C36A N36A -179.5(16) . . . . ?
O31A N31A C36A N36A -6(3) . . . . ?
C32A N31A C36A C35A -1(3) . . . . ?
O31A N31A C36A C35A 172.0(15) . . . . ?
C34A C35A C36A N36A -178.4(16) . . . . ?
C34A C35A C36A N31A 4(3) . . . . ?
C35A C34A N41A C42A -169.3(3) . . . . ?
N33A C34A N41A C42A 11.1(4) . . . . ?
C35A C34A N41A C46A 2.7(3) . . . . ?
N33A C34A N41A C46A -176.9(2) . . . . ?
C34A N41A C42A C43A 112.3(3) . . . . ?
C46A N41A C42A C43A -60.4(3) . . . . ?
N41A C42A C43A C44A 58.1(3) . . . . ?
C42A C43A C44A C45A -56.4(3) . . . . ?
C43A C44A C45A C46A 55.3(3) . . . . ?
C34A N41A C46A C45A -112.9(2) . . . . ?
C42A N41A C46A C45A 60.0(3) . . . . ?
C44A C45A C46A N41A -56.1(2) . . . . ?
C36C N31C C32C N32C -178(4) . . . . ?
O31C N31C C32C N32C -32(6) . . . . ?
C36C N31C C32C N33C -1(8) . . . . ?
O31C N31C C32C N33C 144(4) . . . . ?
N32C C32C N33C C34C 177(4) . . . . ?
N31C C32C N33C C34C 0(7) . . . . ?
C32C N33C C34C N41C -179(3) . . . . ?
C32C N33C C34C C35C -3(3) . . . . ?
N41C C34C C35C C36C -178(3) . . . . ?
N33C C34C C35C C36C 7(3) . . . . ?
C34C C35C C36C N36C -178(4) . . . . ?
C34C C35C C36C N31C -8(7) . . . . ?
C32C N31C C36C N36C 176(4) . . . . ?
O31C N31C C36C N36C 30(6) . . . . ?
C32C N31C C36C C35C 5(8) . . . . ?
O31C N31C C36C C35C -141(4) . . . . ?
N33C C34C N41C C46C 171.9(6) . . . . ?
C35C C34C N41C C46C -4.2(8) . . . . ?
N33C C34C N41C C42C -25.7(8) . . . . ?
C35C C34C N41C C42C 158.2(6) . . . . ?
C34C N41C C42C C43C -106.6(6) . . . . ?
C46C N41C C42C C43C 57.3(8) . . . . ?
N41C C42C C43C C44C -53.9(8) . . . . ?
C42C C43C C44C C45C 52.6(7) . . . . ?
C43C C44C C45C C46C -52.6(7) . . . . ?
C34C N41C C46C C45C 105.1(5) . . . . ?
C42C N41C C46C C45C -58.7(6) . . . . ?
C44C C45C C46C N41C 55.6(6) . . . . ?
O51 C51 C52 C53 -48.68(18) . . . . ?
O50 C51 C52 C53 131.55(13) . . . . ?
C51 C52 C53 C54 174.80(12) . . . . ?
C52 C53 C54 C55 169.68(13) . . . . ?
C53 C54 C55 C56 -172.20(12) . . . . ?
C54 C55 C56 O57 -14.03(19) . . . . ?
C54 C55 C56 O56 166.58(12) . . . . ?

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
O11 H11 O50 0.977(17) 1.525(18) 2.5002(14) 175.3(16) .
O31A H31A O56 0.92(2) 1.487(19) 2.408(9) 177.6(16) .
N16 H16B O51 0.88 2.31 2.9163(15) 126.5 .
N16 H16A O57 0.88 2.01 2.8728(15) 165.2 4_565
N12 H12A O56 0.88 2.07 2.8573(14) 148.7 1_554
N12 H12B O50 0.88 2.14 2.9340(14) 150.5 3_565
N32A H32A O51 0.88 2.00 2.864(7) 166.8 4_666
N32C H32F O57 0.88 2.05 2.831(17) 147.8 .
N36A H36B O50 0.88 2.16 2.915(10) 144.2 1_556

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048

# Attachment '_6__cif1.cif'

data_ns0801m
_database_code_depnum_ccdc_archive 'CCDC 733880'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3189-76-06 minoxidil : 4-hydroxybenzoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O1)3 (C7 H6 O3)2 (H2 O1)2
;
_chemical_formula_sum            'C41 H61 N15 O11'
_chemical_formula_weight         940.05

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.8421(9)
_cell_length_b                   11.7743(6)
_cell_length_c                   21.9811(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.245(2)
_cell_angle_gamma                90.00
_cell_volume                     4512.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      32.39

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_T_max  0.9797
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34412
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         32.57
_reflns_number_total             8116
_reflns_number_gt                6393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8116
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1S O 0.60871(4) 0.38344(6) 0.34546(3) 0.02339(14) Uani 1 1 d . . .
H1A H 0.5716(8) 0.4008(12) 0.3140(6) 0.028 Uiso 1 1 d . . .
H1B H 0.6508(8) 0.3917(11) 0.3303(6) 0.028 Uiso 1 1 d . . .
N11 N 0.63660(4) 0.14274(7) 0.89072(4) 0.02143(15) Uani 1 1 d . . .
C12 C 0.68663(5) 0.10877(8) 0.85794(4) 0.01954(16) Uani 1 1 d . . .
N12 N 0.69718(5) -0.00142(7) 0.84915(4) 0.02547(17) Uani 1 1 d . . .
H12A H 0.6686(8) -0.0525(12) 0.8653(6) 0.031 Uiso 1 1 d . . .
H12B H 0.7265(8) -0.0248(12) 0.8281(6) 0.031 Uiso 1 1 d . . .
N13 N 0.72948(4) 0.18370(6) 0.83208(4) 0.01927(15) Uani 1 1 d . . .
O13 O 0.78626(4) 0.14164(6) 0.80408(3) 0.02107(13) Uani 1 1 d . . .
C14 C 0.72470(6) 0.29833(7) 0.84202(4) 0.02039(17) Uani 1 1 d . . .
N14 N 0.77247(6) 0.36504(7) 0.81818(4) 0.02811(19) Uani 1 1 d . . .
H14A H 0.7886(8) 0.3348(13) 0.7853(7) 0.034 Uiso 1 1 d . . .
H14B H 0.7643(8) 0.4400(13) 0.8198(6) 0.034 Uiso 1 1 d . . .
C15 C 0.67378(6) 0.33623(8) 0.87626(4) 0.02155(17) Uani 1 1 d . . .
H15 H 0.6690 0.4150 0.8839 0.026 Uiso 1 1 calc R . .
C16 C 0.62876(5) 0.25597(8) 0.89982(4) 0.01985(17) Uani 1 1 d . . .
N21 N 0.57532(5) 0.28619(7) 0.93187(4) 0.02500(17) Uani 1 1 d . . .
C22 C 0.53320(6) 0.20157(9) 0.96059(5) 0.0268(2) Uani 1 1 d . . .
H22A H 0.5363 0.1265 0.9410 0.032 Uiso 1 1 calc R . .
H22B H 0.4785 0.2235 0.9538 0.032 Uiso 1 1 calc R . .
C23 C 0.56705(6) 0.19388(9) 1.02977(5) 0.0288(2) Uani 1 1 d . . .
H23A H 0.6201 0.1642 1.0364 0.035 Uiso 1 1 calc R . .
H23B H 0.5364 0.1403 1.0493 0.035 Uiso 1 1 calc R . .
C24 C 0.56786(6) 0.31037(9) 1.06069(5) 0.0299(2) Uani 1 1 d . . .
H24A H 0.5146 0.3343 1.0603 0.036 Uiso 1 1 calc R . .
H24B H 0.5958 0.3051 1.1046 0.036 Uiso 1 1 calc R . .
C25 C 0.60625(6) 0.39873(9) 1.02692(6) 0.0319(2) Uani 1 1 d . . .
H25A H 0.6617 0.3816 1.0331 0.038 Uiso 1 1 calc R . .
H25B H 0.6007 0.4748 1.0447 0.038 Uiso 1 1 calc R . .
C26 C 0.57048(7) 0.39955(9) 0.95749(5) 0.0316(2) Uani 1 1 d . . .
H26A H 0.5161 0.4233 0.9509 0.038 Uiso 1 1 calc R . .
H26B H 0.5979 0.4545 0.9360 0.038 Uiso 1 1 calc R . .
N31 N 0.4513(2) 0.7373(4) 0.2823(2) 0.0211(2) Uani 0.50 1 d P A -1
C32 C 0.4502(3) 0.6266(2) 0.2843(3) 0.0168(6) Uani 0.50 1 d P A -1
N32 N 0.4116(3) 0.5606(3) 0.3062(3) 0.0238(5) Uani 0.50 1 d P A -1
H32A H 0.3748(19) 0.595(3) 0.3315(13) 0.029 Uiso 0.50 1 d P B -1
H32B H 0.3992(18) 0.491(3) 0.2961(15) 0.029 Uiso 0.50 1 d P C -1
N33 N 0.4968(6) 0.56824(11) 0.2527(7) 0.0171(10) Uani 0.50 1 d P A -1
O33 O 0.4977(12) 0.45155(9) 0.2485(12) 0.0229(7) Uani 0.50 1 d P A -1
C34 C 0.5435(3) 0.6243(3) 0.2227(3) 0.0168(6) Uani 0.50 1 d P A -1
N34 N 0.5928(3) 0.5658(3) 0.1846(3) 0.0238(5) Uani 0.50 1 d P A -1
H34A H 0.5852(19) 0.488(4) 0.1900(15) 0.029 Uiso 0.50 1 d P D -1
H34B H 0.6355(19) 0.596(3) 0.1904(13) 0.029 Uiso 0.50 1 d P E -1
C35 C 0.5456(3) 0.7443(4) 0.2193(3) 0.0211(2) Uani 0.50 1 d P A -1
H35 H 0.5769 0.7842 0.1965 0.025 Uiso 0.50 1 calc PR A -1
C36 C 0.4983(8) 0.79751(13) 0.2518(8) 0.0195(7) Uani 0.50 1 d P A -1
N41 N 0.4937(2) 0.91332(12) 0.25803(14) 0.0200(5) Uani 0.50 1 d P A -1
C42 C 0.43763(11) 0.95946(16) 0.29173(9) 0.0221(2) Uani 0.50 1 d P A -1
H42A H 0.4346 0.9089 0.3271 0.027 Uiso 0.50 1 calc PR A -1
H42B H 0.3864 0.9613 0.2635 0.027 Uiso 0.50 1 calc PR A -1
C43 C 0.45890(11) 1.07792(17) 0.31591(10) 0.0253(3) Uani 0.50 1 d P A -1
H43A H 0.5069 1.0749 0.3482 0.030 Uiso 0.50 1 calc PR A -1
H43B H 0.4179 1.1085 0.3354 0.030 Uiso 0.50 1 calc PR A -1
C44 C 0.46989(13) 1.1564(2) 0.26326(11) 0.0276(4) Uani 0.50 1 d P A -1
H44A H 0.4839 1.2335 0.2798 0.033 Uiso 0.50 1 calc PR A -1
H44B H 0.4214 1.1619 0.2316 0.033 Uiso 0.50 1 calc PR A -1
C45 C 0.53336(13) 1.1093(2) 0.23345(11) 0.0253(3) Uani 0.50 1 d P A -1
H45A H 0.5380 1.1574 0.1975 0.030 Uiso 0.50 1 calc PR A -1
H45B H 0.5828 1.1125 0.2640 0.030 Uiso 0.50 1 calc PR A -1
C46 C 0.51751(11) 0.98752(16) 0.21167(9) 0.0221(2) Uani 0.50 1 d P A -1
H46A H 0.4767 0.9876 0.1733 0.027 Uiso 0.50 1 calc PR A -1
H46B H 0.5644 0.9557 0.2010 0.027 Uiso 0.50 1 calc PR A -1
C51 C 0.69057(5) 0.20008(7) 0.59162(4) 0.01664(15) Uani 1 1 d . . .
C57 C 0.72129(5) 0.20799(7) 0.66011(4) 0.01696(15) Uani 1 1 d . . .
O51 O 0.74242(4) 0.11459(5) 0.68963(3) 0.02112(13) Uani 1 1 d . . .
O52 O 0.72710(4) 0.30229(5) 0.68622(3) 0.02132(13) Uani 1 1 d . . .
C52 C 0.67359(5) 0.09596(8) 0.56136(4) 0.02092(17) Uani 1 1 d . . .
H52 H 0.6802 0.0277 0.5849 0.025 Uiso 1 1 calc R . .
C53 C 0.64728(6) 0.09116(8) 0.49743(4) 0.02299(18) Uani 1 1 d . . .
H53 H 0.6355 0.0200 0.4773 0.028 Uiso 1 1 calc R . .
C54 C 0.63813(5) 0.19129(8) 0.46264(4) 0.01949(17) Uani 1 1 d . . .
O54 O 0.61377(4) 0.18218(6) 0.39991(3) 0.02585(15) Uani 1 1 d . . .
H54 H 0.6126(8) 0.2510(13) 0.3832(7) 0.031 Uiso 1 1 d . . .
C55 C 0.65415(5) 0.29579(7) 0.49218(4) 0.01832(16) Uani 1 1 d . . .
H55 H 0.6473 0.3641 0.4686 0.022 Uiso 1 1 calc R . .
C56 C 0.68008(5) 0.29937(7) 0.55612(4) 0.01766(16) Uani 1 1 d . . .
H56 H 0.6909 0.3707 0.5762 0.021 Uiso 1 1 calc R . .
H13 H 0.7637(7) 0.1306(10) 0.7591(6) 0.021 Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1S H1A 0.875(14) . ?
O1S H1B 0.890(14) . ?
N11 C12 1.3225(12) . ?
N11 C16 1.3597(12) . ?
C12 N12 1.3309(12) . ?
C12 N13 1.3675(12) . ?
N12 H12A 0.907(14) . ?
N12 H12B 0.817(14) . ?
N13 C14 1.3727(12) . ?
N13 O13 1.3839(10) . ?
O13 H13 0.994(12) . ?
C14 N14 1.3444(12) . ?
C14 C15 1.3714(13) . ?
N14 H14A 0.905(15) . ?
N14 H14B 0.896(15) . ?
C15 C16 1.4082(13) . ?
C15 H15 0.9500 . ?
C16 N21 1.3481(12) . ?
N21 C26 1.4583(13) . ?
N21 C22 1.4687(13) . ?
C22 C23 1.5151(15) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5295(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5226(16) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5243(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
N31 C32 1.305(5) . ?
N31 C36 1.377(13) . ?
C32 N32 1.204(8) . ?
C32 N33 1.376(13) . ?
N32 H32A 1.03(3) . ?
N32 H32B 0.87(4) . ?
N33 C34 1.340(13) . ?
N33 O33 1.377(3) . ?
C34 C35 1.416(6) . ?
C34 N34 1.504(9) . ?
N34 H34A 0.93(4) . ?
N34 H34B 0.83(3) . ?
C35 C36 1.367(13) . ?
C35 H35 0.9500 . ?
C36 N41 1.375(3) . ?
N41 C42 1.470(3) . ?
N41 C46 1.471(2) . ?
C42 C43 1.512(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.526(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.528(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.519(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C51 C56 1.3960(12) . ?
C51 C52 1.3970(12) . ?
C51 C57 1.4919(12) . ?
C57 O52 1.2441(11) . ?
C57 O51 1.2917(11) . ?
C52 C53 1.3851(13) . ?
C52 H52 0.9500 . ?
C53 C54 1.3959(13) . ?
C53 H53 0.9500 . ?
C54 O54 1.3592(11) . ?
C54 C55 1.3923(12) . ?
O54 H54 0.888(15) . ?
C55 C56 1.3838(12) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?

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
H1A O1S H1B 103.6(12) . . ?
C12 N11 C16 118.62(8) . . ?
N11 C12 N12 120.43(9) . . ?
N11 C12 N13 122.19(8) . . ?
N12 C12 N13 117.38(8) . . ?
C12 N12 H12A 118.8(9) . . ?
C12 N12 H12B 122.6(10) . . ?
H12A N12 H12B 118.5(13) . . ?
C12 N13 C14 120.61(8) . . ?
C12 N13 O13 118.72(7) . . ?
C14 N13 O13 119.91(7) . . ?
N13 O13 H13 108.0(7) . . ?
N14 C14 C15 124.91(9) . . ?
N14 C14 N13 116.52(8) . . ?
C15 C14 N13 118.55(8) . . ?
C14 N14 H14A 114.6(9) . . ?
C14 N14 H14B 116.1(9) . . ?
H14A N14 H14B 120.0(13) . . ?
C14 C15 C16 118.64(8) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N21 C16 N11 116.22(8) . . ?
N21 C16 C15 122.48(8) . . ?
N11 C16 C15 121.30(8) . . ?
C16 N21 C26 123.34(9) . . ?
C16 N21 C22 121.92(8) . . ?
C26 N21 C22 112.18(8) . . ?
N21 C22 C23 109.91(8) . . ?
N21 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
N21 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C22 C23 C24 110.89(9) . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 111.04(9) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 110.88(9) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
N21 C26 C25 109.53(9) . . ?
N21 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
N21 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.2 . . ?
C32 N31 C36 123.1(5) . . ?
N32 C32 N31 132.3(5) . . ?
N32 C32 N33 109.8(4) . . ?
N31 C32 N33 117.8(6) . . ?
C32 N32 H32A 116.7(19) . . ?
C32 N32 H32B 130(3) . . ?
H32A N32 H32B 111(3) . . ?
C34 N33 C32 120.52(13) . . ?
C34 N33 O33 116.2(14) . . ?
C32 N33 O33 123.3(14) . . ?
N33 C34 C35 123.0(6) . . ?
N33 C34 N34 123.1(4) . . ?
C35 C34 N34 113.7(4) . . ?
C34 N34 H34A 105(2) . . ?
C34 N34 H34B 110(2) . . ?
H34A N34 H34B 124(3) . . ?
C36 C35 C34 113.8(5) . . ?
C36 C35 H35 123.1 . . ?
C34 C35 H35 123.1 . . ?
C35 C36 N41 124.3(9) . . ?
C35 C36 N31 121.73(14) . . ?
N41 C36 N31 114.0(9) . . ?
C36 N41 C42 118.6(6) . . ?
C36 N41 C46 119.2(7) . . ?
C42 N41 C46 117.17(17) . . ?
N41 C42 C43 111.79(17) . . ?
N41 C42 H42A 109.3 . . ?
C43 C42 H42A 109.3 . . ?
N41 C42 H42B 109.3 . . ?
C43 C42 H42B 109.3 . . ?
H42A C42 H42B 107.9 . . ?
C42 C43 C44 110.79(17) . . ?
C42 C43 H43A 109.5 . . ?
C44 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 108.1 . . ?
C43 C44 C45 109.38(17) . . ?
C43 C44 H44A 109.8 . . ?
C45 C44 H44A 109.8 . . ?
C43 C44 H44B 109.8 . . ?
C45 C44 H44B 109.8 . . ?
H44A C44 H44B 108.2 . . ?
C46 C45 C44 111.86(16) . . ?
C46 C45 H45A 109.2 . . ?
C44 C45 H45A 109.2 . . ?
C46 C45 H45B 109.2 . . ?
C44 C45 H45B 109.2 . . ?
H45A C45 H45B 107.9 . . ?
N41 C46 C45 113.82(17) . . ?
N41 C46 H46A 108.8 . . ?
C45 C46 H46A 108.8 . . ?
N41 C46 H46B 108.8 . . ?
C45 C46 H46B 108.8 . . ?
H46A C46 H46B 107.7 . . ?
C56 C51 C52 118.62(8) . . ?
C56 C51 C57 119.26(8) . . ?
C52 C51 C57 122.10(8) . . ?
O52 C57 O51 122.76(8) . . ?
O52 C57 C51 119.87(8) . . ?
O51 C57 C51 117.35(7) . . ?
C53 C52 C51 120.76(8) . . ?
C53 C52 H52 119.6 . . ?
C51 C52 H52 119.6 . . ?
C52 C53 C54 119.77(8) . . ?
C52 C53 H53 120.1 . . ?
C54 C53 H53 120.1 . . ?
O54 C54 C55 122.19(8) . . ?
O54 C54 C53 117.66(8) . . ?
C55 C54 C53 120.15(8) . . ?
C54 O54 H54 108.8(9) . . ?
C56 C55 C54 119.47(8) . . ?
C56 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?
C55 C56 C51 121.23(8) . . ?
C55 C56 H56 119.4 . . ?
C51 C56 H56 119.4 . . ?

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
C16 N11 C12 N12 178.53(9) . . . . ?
C16 N11 C12 N13 -1.23(13) . . . . ?
N11 C12 N13 C14 3.30(13) . . . . ?
N12 C12 N13 C14 -176.47(8) . . . . ?
N11 C12 N13 O13 173.26(8) . . . . ?
N12 C12 N13 O13 -6.51(12) . . . . ?
C12 N13 C14 N14 175.82(8) . . . . ?
O13 N13 C14 N14 5.98(12) . . . . ?
C12 N13 C14 C15 -2.64(13) . . . . ?
O13 N13 C14 C15 -172.48(8) . . . . ?
N14 C14 C15 C16 -178.19(9) . . . . ?
N13 C14 C15 C16 0.13(13) . . . . ?
C12 N11 C16 N21 177.99(8) . . . . ?
C12 N11 C16 C15 -1.37(13) . . . . ?
C14 C15 C16 N21 -177.42(9) . . . . ?
C14 C15 C16 N11 1.91(14) . . . . ?
N11 C16 N21 C26 166.17(9) . . . . ?
C15 C16 N21 C26 -14.47(15) . . . . ?
N11 C16 N21 C22 5.76(13) . . . . ?
C15 C16 N21 C22 -174.88(9) . . . . ?
C16 N21 C22 C23 101.06(10) . . . . ?
C26 N21 C22 C23 -61.34(11) . . . . ?
N21 C22 C23 C24 55.60(11) . . . . ?
C22 C23 C24 C25 -52.30(12) . . . . ?
C23 C24 C25 C26 52.60(12) . . . . ?
C16 N21 C26 C25 -100.65(11) . . . . ?
C22 N21 C26 C25 61.45(11) . . . . ?
C24 C25 C26 N21 -56.44(12) . . . . ?
C36 N31 C32 N32 -176.6(10) . . . . ?
C36 N31 C32 N33 -2.0(12) . . . . ?
N32 C32 N33 C34 178.0(8) . . . . ?
N31 C32 N33 C34 2.3(15) . . . . ?
N32 C32 N33 O33 -0.7(17) . . . . ?
N31 C32 N33 O33 -176.4(14) . . . . ?
C32 N33 C34 C35 -2.9(16) . . . . ?
O33 N33 C34 C35 175.9(12) . . . . ?
C32 N33 C34 N34 -176.8(6) . . . . ?
O33 N33 C34 N34 2.0(17) . . . . ?
N33 C34 C35 C36 3.0(12) . . . . ?
N34 C34 C35 C36 177.4(8) . . . . ?
C34 C35 C36 N41 176.3(10) . . . . ?
C34 C35 C36 N31 -2.6(16) . . . . ?
C32 N31 C36 C35 2.3(18) . . . . ?
C32 N31 C36 N41 -176.7(7) . . . . ?
C35 C36 N41 C42 177.0(9) . . . . ?
N31 C36 N41 C42 -4.0(14) . . . . ?
C35 C36 N41 C46 22.9(16) . . . . ?
N31 C36 N41 C46 -158.1(8) . . . . ?
C36 N41 C42 C43 158.2(8) . . . . ?
C46 N41 C42 C43 -47.2(3) . . . . ?
N41 C42 C43 C44 54.7(3) . . . . ?
C42 C43 C44 C45 -59.3(2) . . . . ?
C43 C44 C45 C46 55.1(2) . . . . ?
C36 N41 C46 C45 -162.1(7) . . . . ?
C42 N41 C46 C45 43.4(4) . . . . ?
C44 C45 C46 N41 -46.9(3) . . . . ?
C56 C51 C57 O52 10.05(12) . . . . ?
C52 C51 C57 O52 -171.56(8) . . . . ?
C56 C51 C57 O51 -168.53(8) . . . . ?
C52 C51 C57 O51 9.86(12) . . . . ?
C56 C51 C52 C53 0.33(13) . . . . ?
C57 C51 C52 C53 -178.07(8) . . . . ?
C51 C52 C53 C54 0.52(14) . . . . ?
C52 C53 C54 O54 178.59(9) . . . . ?
C52 C53 C54 C55 -1.08(14) . . . . ?
O54 C54 C55 C56 -178.86(8) . . . . ?
C53 C54 C55 C56 0.79(13) . . . . ?
C54 C55 C56 C51 0.06(13) . . . . ?
C52 C51 C56 C55 -0.62(13) . . . . ?
C57 C51 C56 C55 177.82(8) . . . . ?

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
O13 H13 O51 0.994(12) 1.505(13) 2.4915(9) 171.0(11) .
O54 H54 O1S 0.888(15) 1.760(15) 2.6477(10) 176.4(14) .
O1S H1A O33 0.875(14) 1.83(2) 2.70(2) 174.3(13) .
O1S H1B O51 0.890(14) 2.044(14) 2.9189(10) 167.3(12) 7_656
N12 H12A O54 0.907(14) 2.046(14) 2.9485(12) 173.1(12) 6_556
N12 H12B O52 0.817(14) 2.245(14) 2.8665(11) 133.3(12) 4_646
N14 H14B O51 0.896(15) 2.067(16) 2.9520(11) 169.1(13) 4_656
N32 H32A O52 1.03(3) 2.15(3) 2.989(4) 137(2) 5_666
N34 H34B O52 0.83(3) 2.04(3) 2.850(4) 165(3) 6_565

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        32.57
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.049

# Attachment '_7__cif1.cif'

data_ns0809m
_database_code_depnum_ccdc_archive 'CCDC 733881'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3262-11-02 minoxidil : 1-hydroxy-2-naphthoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O) (C11 H8 O3)2
;
_chemical_formula_sum            'C31 H31 N5 O7'
_chemical_formula_weight         585.61

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2003(5)
_cell_length_b                   30.8973(13)
_cell_length_c                   10.1214(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.917(2)
_cell_angle_gamma                90.00
_cell_volume                     2818.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      32.22

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51264
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         32.75
_reflns_number_total             9840
_reflns_number_gt                6701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+1.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9840
_refine_ls_number_parameters     509
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N11 N 0.68295(14) 0.48861(4) 0.43094(14) 0.0321(3) Uani 1 1 d . A .
O11 O 0.78139(12) 0.51785(4) 0.42034(12) 0.0347(2) Uani 1 1 d . . .
H11 H 0.832(2) 0.5003(6) 0.383(2) 0.042 Uiso 1 1 d . . .
C12 C 0.71327(18) 0.47314(6) 0.56916(17) 0.0376(3) Uani 1 1 d . . .
N12 N 0.84066(18) 0.48530(7) 0.68296(17) 0.0495(4) Uani 1 1 d . A .
H12A H 0.856(3) 0.4745(8) 0.765(3) 0.059 Uiso 1 1 d . . .
H12B H 0.910(3) 0.5001(8) 0.677(3) 0.059 Uiso 1 1 d . . .
N13 N 0.61368(18) 0.44679(6) 0.58143(17) 0.0398(4) Uani 0.474(16) 1 d P A 1
C13 C 0.61368(18) 0.44679(6) 0.58143(17) 0.0398(4) Uani 0.526(16) 1 d P A 2
H13 H 0.6329 0.4354 0.6760 0.048 Uiso 0.526(16) 1 calc PR A 2
C14 C 0.48416(19) 0.43659(6) 0.45534(18) 0.0373(3) Uani 1 1 d . . .
C15 C 0.45521(18) 0.45235(5) 0.31732(16) 0.0383(4) Uani 0.474(16) 1 d P A 1
H15 H 0.3667 0.4445 0.2306 0.046 Uiso 0.474(16) 1 calc PR A 1
N15 N 0.45521(18) 0.45235(5) 0.31732(16) 0.0383(4) Uani 0.526(16) 1 d P A 2
C16 C 0.55327(17) 0.47893(5) 0.30680(17) 0.0345(3) Uani 1 1 d . . .
N16 N 0.53276(17) 0.49691(6) 0.17871(16) 0.0416(3) Uani 1 1 d . A .
H16A H 0.457(3) 0.4899(7) 0.102(3) 0.050 Uiso 1 1 d . . .
H16B H 0.599(3) 0.5146(7) 0.176(2) 0.050 Uiso 1 1 d . . .
N21A N 0.3890(17) 0.4088(4) 0.4741(10) 0.0448(14) Uani 0.617(4) 1 d PD A 1
C22A C 0.4233(9) 0.3889(2) 0.6189(8) 0.0445(12) Uani 0.617(4) 1 d PD A 1
H22A H 0.3647 0.4033 0.6612 0.053 Uiso 0.617(4) 1 calc PR A 1
H22B H 0.5298 0.3931 0.6895 0.053 Uiso 0.617(4) 1 calc PR A 1
C23A C 0.3883(6) 0.34095(19) 0.6017(5) 0.0501(9) Uani 0.617(4) 1 d PD A 1
H23A H 0.4594 0.3259 0.5766 0.060 Uiso 0.617(4) 1 calc PR A 1
H23B H 0.4010 0.3293 0.6981 0.060 Uiso 0.617(4) 1 calc PR A 1
C24A C 0.2320(5) 0.33177(12) 0.4814(5) 0.0604(9) Uani 0.617(4) 1 d PD A 1
H24A H 0.1599 0.3441 0.5107 0.072 Uiso 0.617(4) 1 calc PR A 1
H24B H 0.2158 0.3001 0.4692 0.072 Uiso 0.617(4) 1 calc PR A 1
C25A C 0.2082(6) 0.35178(13) 0.3336(5) 0.0596(10) Uani 0.617(4) 1 d PD A 1
H25A H 0.2735 0.3374 0.2992 0.072 Uiso 0.617(4) 1 calc PR A 1
H25B H 0.1040 0.3474 0.2564 0.072 Uiso 0.617(4) 1 calc PR A 1
C26A C 0.2427(14) 0.3998(2) 0.3541(7) 0.0453(12) Uani 0.617(4) 1 d PD A 1
H26A H 0.2344 0.4118 0.2598 0.054 Uiso 0.617(4) 1 calc PR A 1
H26B H 0.1682 0.4145 0.3750 0.054 Uiso 0.617(4) 1 calc PR A 1
N21B N 0.374(3) 0.4150(7) 0.4549(18) 0.0448(14) Uani 0.383(4) 1 d PD A 2
C22B C 0.3923(18) 0.3930(4) 0.5928(14) 0.0445(12) Uani 0.383(4) 1 d PD A 2
H22C H 0.3034 0.3977 0.6064 0.053 Uiso 0.383(4) 1 calc PR A 2
H22D H 0.4796 0.4049 0.6810 0.053 Uiso 0.383(4) 1 calc PR A 2
C23B C 0.4136(11) 0.3452(3) 0.5778(10) 0.0501(9) Uani 0.383(4) 1 d PD A 2
H23C H 0.4212 0.3297 0.6667 0.060 Uiso 0.383(4) 1 calc PR A 2
H23D H 0.5070 0.3405 0.5724 0.060 Uiso 0.383(4) 1 calc PR A 2
C24B C 0.2831(8) 0.3273(2) 0.4369(7) 0.0604(9) Uani 0.383(4) 1 d PD A 2
H24C H 0.1923 0.3280 0.4490 0.072 Uiso 0.383(4) 1 calc PR A 2
H24D H 0.3030 0.2968 0.4224 0.072 Uiso 0.383(4) 1 calc PR A 2
C25B C 0.2579(10) 0.3538(2) 0.2991(8) 0.0596(10) Uani 0.383(4) 1 d PD A 2
H25C H 0.3437 0.3502 0.2796 0.072 Uiso 0.383(4) 1 calc PR A 2
H25D H 0.1683 0.3431 0.2107 0.072 Uiso 0.383(4) 1 calc PR A 2
C26B C 0.238(2) 0.4014(4) 0.3225(14) 0.0453(12) Uani 0.383(4) 1 d PD A 2
H26C H 0.2246 0.4185 0.2340 0.054 Uiso 0.383(4) 1 calc PR A 2
H26D H 0.1508 0.4057 0.3385 0.054 Uiso 0.383(4) 1 calc PR A 2
C31A C 0.6025(3) 0.34265(6) 0.1886(2) 0.0471(5) Uani 0.943(2) 1 d PD B 1
C32A C 0.6560(2) 0.37941(6) 0.14225(18) 0.0423(5) Uani 0.943(2) 1 d PD B 1
O32A O 0.59306(19) 0.38748(5) -0.00571(15) 0.0508(4) Uani 0.943(2) 1 d PD B 1
H32A H 0.6259 0.4109 -0.0203 0.061 Uiso 0.943(2) 1 calc PR B 1
C33A C 0.7673(2) 0.40533(7) 0.24726(19) 0.0421(4) Uani 0.943(2) 1 d PD B 1
C34A C 0.8275(3) 0.39464(10) 0.4012(2) 0.0481(5) Uani 0.943(2) 1 d PD B 1
H34A H 0.9046 0.4121 0.4732 0.058 Uiso 0.943(2) 1 calc PR B 1
C35A C 0.7776(2) 0.36009(7) 0.4482(2) 0.0513(5) Uani 0.943(2) 1 d PD B 1
H35A H 0.8192 0.3539 0.5520 0.062 Uiso 0.943(2) 1 calc PR B 1
C36A C 0.6639(2) 0.33326(7) 0.3433(2) 0.0475(5) Uani 0.943(2) 1 d PD B 1
C37A C 0.6091(4) 0.29656(10) 0.3870(3) 0.0586(6) Uani 0.943(2) 1 d PD B 1
H37A H 0.6502 0.2896 0.4901 0.070 Uiso 0.943(2) 1 calc PR B 1
C38A C 0.4994(6) 0.27126(15) 0.2846(4) 0.0683(13) Uani 0.943(2) 1 d PD B 1
H38A H 0.4640 0.2471 0.3168 0.082 Uiso 0.943(2) 1 calc PR B 1
C39A C 0.4385(4) 0.28079(8) 0.1314(3) 0.0760(9) Uani 0.943(2) 1 d PD B 1
H39A H 0.3623 0.2629 0.0602 0.091 Uiso 0.943(2) 1 calc PR B 1
C40A C 0.4884(3) 0.31569(7) 0.0842(2) 0.0618(7) Uani 0.943(2) 1 d PD B 1
H40A H 0.4461 0.3219 -0.0196 0.074 Uiso 0.943(2) 1 calc PR B 1
C41A C 0.8198(3) 0.44470(8) 0.2033(2) 0.0431(5) Uani 0.943(2) 1 d PD B 1
O41A O 0.7724(2) 0.45185(6) 0.06322(17) 0.0491(4) Uani 0.943(2) 1 d PD B 1
O42A O 0.9076(3) 0.47003(7) 0.3031(2) 0.0453(5) Uani 0.943(2) 1 d PD B 1
C31B C 0.681(3) 0.3467(7) 0.289(2) 0.0471(5) Uani 0.057(2) 1 d PD B 2
C32B C 0.767(3) 0.3850(7) 0.300(2) 0.0423(5) Uani 0.057(2) 1 d PD B 2
O32B O 0.866(3) 0.3984(12) 0.435(3) 0.0481(5) Uani 0.057(2) 1 d PD B 2
H32B H 0.9084 0.4208 0.4272 0.058 Uiso 0.057(2) 1 calc PR B 2
C33B C 0.742(3) 0.4059(7) 0.168(2) 0.0421(4) Uani 0.057(2) 1 d PD B 2
C34B C 0.651(4) 0.3841(10) 0.032(2) 0.0508(4) Uani 0.057(2) 1 d PD B 2
H34B H 0.6533 0.3940 -0.0552 0.061 Uiso 0.057(2) 1 calc PR B 2
C35B C 0.560(3) 0.3504(9) 0.018(2) 0.0513(5) Uani 0.057(2) 1 d PD B 2
H35B H 0.4889 0.3408 -0.0783 0.062 Uiso 0.057(2) 1 calc PR B 2
C36B C 0.575(4) 0.3298(11) 0.149(2) 0.0618(7) Uani 0.057(2) 1 d PD B 2
C37B C 0.490(6) 0.2932(14) 0.148(4) 0.0760(9) Uani 0.057(2) 1 d PD B 2
H37B H 0.4100 0.2837 0.0562 0.091 Uiso 0.057(2) 1 calc PR B 2
C38B C 0.523(12) 0.272(2) 0.276(4) 0.0683(13) Uani 0.057(2) 1 d PD B 2
H38B H 0.4825 0.2437 0.2728 0.082 Uiso 0.057(2) 1 calc PR B 2
C39B C 0.616(8) 0.291(2) 0.416(4) 0.0586(6) Uani 0.057(2) 1 d PD B 2
H39B H 0.6214 0.2794 0.5051 0.070 Uiso 0.057(2) 1 calc PR B 2
C40B C 0.700(4) 0.3261(9) 0.422(3) 0.0475(5) Uani 0.057(2) 1 d PD B 2
H40B H 0.7713 0.3369 0.5161 0.057 Uiso 0.057(2) 1 calc PR B 2
C41B C 0.821(5) 0.4456(11) 0.167(3) 0.0431(5) Uani 0.057(2) 1 d PD B 2
O41B O 0.911(5) 0.4617(15) 0.292(4) 0.0453(5) Uani 0.057(2) 1 d PD B 2
O42B O 0.791(4) 0.4643(10) 0.042(3) 0.0491(4) Uani 0.057(2) 1 d PD B 2
C51A C 0.9507(9) 0.6686(2) 0.1718(10) 0.0368(10) Uani 0.583(4) 1 d PD C 1
C52A C 0.8662(13) 0.6296(3) 0.1443(15) 0.0336(11) Uani 0.583(4) 1 d PD C 1
O52A O 0.760(2) 0.6288(5) 0.187(3) 0.0423(14) Uani 0.583(4) 1 d PD C 1
H52A H 0.7159 0.6049 0.1642 0.051 Uiso 0.583(4) 1 calc PR C 1
C53A C 0.9006(11) 0.5932(2) 0.0844(13) 0.0321(11) Uani 0.583(4) 1 d PD C 1
C54A C 1.0187(7) 0.59595(14) 0.0466(7) 0.0383(10) Uani 0.583(4) 1 d PD C 1
H54A H 1.0426 0.5713 0.0060 0.046 Uiso 0.583(4) 1 calc PR C 1
C55A C 1.0975(6) 0.63284(15) 0.0674(6) 0.0431(10) Uani 0.583(4) 1 d PD C 1
H55A H 1.1741 0.6338 0.0390 0.052 Uiso 0.583(4) 1 calc PR C 1
C56A C 1.0674(6) 0.67001(16) 0.1308(6) 0.0398(10) Uani 0.583(4) 1 d PD C 1
C57A C 1.1489(6) 0.70924(17) 0.1581(7) 0.0540(12) Uani 0.583(4) 1 d PD C 1
H57A H 1.2268 0.7111 0.1318 0.065 Uiso 0.583(4) 1 calc PR C 1
C58A C 1.1183(7) 0.7443(2) 0.2208(8) 0.0599(14) Uani 0.583(4) 1 d PD C 1
H58A H 1.1744 0.7701 0.2371 0.072 Uiso 0.583(4) 1 calc PR C 1
C59A C 1.0039(8) 0.7424(2) 0.2617(8) 0.0568(12) Uani 0.583(4) 1 d PD C 1
H59A H 0.9836 0.7669 0.3060 0.068 Uiso 0.583(4) 1 calc PR C 1
C60A C 0.9220(12) 0.7054(3) 0.2379(13) 0.0481(13) Uani 0.583(4) 1 d PD C 1
H60A H 0.8452 0.7044 0.2659 0.058 Uiso 0.583(4) 1 calc PR C 1
C61A C 0.8183(12) 0.5530(2) 0.0667(16) 0.0315(10) Uani 0.583(4) 1 d PD C 1
O61A O 0.7061(10) 0.5514(5) 0.0850(14) 0.0355(12) Uani 0.583(4) 1 d PD C 1
O62A O 0.8656(6) 0.51929(13) 0.0235(7) 0.0357(7) Uani 0.583(4) 1 d PD C 1
H62A H 0.8332 0.4966 0.0439 0.043 Uiso 0.583(4) 1 calc PR C 1
C51B C 0.9448(14) 0.6790(3) 0.1935(16) 0.0368(10) Uani 0.417(4) 1 d PD C 2
C52B C 0.874(2) 0.6377(4) 0.167(2) 0.0336(11) Uani 0.417(4) 1 d PD C 2
O52B O 0.763(3) 0.6352(7) 0.204(4) 0.0423(14) Uani 0.417(4) 1 d PD C 2
H52B H 0.7091 0.6138 0.1606 0.051 Uiso 0.417(4) 1 calc PR C 2
C53B C 0.9113(16) 0.6043(3) 0.100(2) 0.0321(11) Uani 0.417(4) 1 d PD C 2
C54B C 1.0294(10) 0.6115(2) 0.0637(11) 0.0383(10) Uani 0.417(4) 1 d PD C 2
H54B H 1.0584 0.5887 0.0199 0.046 Uiso 0.417(4) 1 calc PR C 2
C55B C 1.1004(9) 0.6500(2) 0.0899(9) 0.0431(10) Uani 0.417(4) 1 d PD C 2
H55B H 1.1791 0.6537 0.0657 0.052 Uiso 0.417(4) 1 calc PR C 2
C56B C 1.0591(9) 0.6848(2) 0.1528(10) 0.0398(10) Uani 0.417(4) 1 d PD C 2
C57B C 1.1321(10) 0.7259(3) 0.1841(10) 0.0540(12) Uani 0.417(4) 1 d PD C 2
H57B H 1.2103 0.7307 0.1598 0.065 Uiso 0.417(4) 1 calc PR C 2
C58B C 1.0914(11) 0.7579(3) 0.2475(12) 0.0599(14) Uani 0.417(4) 1 d PD C 2
H58B H 1.1382 0.7854 0.2633 0.072 Uiso 0.417(4) 1 calc PR C 2
C59B C 0.9805(12) 0.7512(3) 0.2908(13) 0.0568(12) Uani 0.417(4) 1 d PD C 2
H59B H 0.9567 0.7736 0.3404 0.068 Uiso 0.417(4) 1 calc PR C 2
C60B C 0.9067(18) 0.7126(4) 0.262(2) 0.0481(13) Uani 0.417(4) 1 d PD C 2
H60B H 0.8295 0.7086 0.2882 0.058 Uiso 0.417(4) 1 calc PR C 2
C61B C 0.8364(18) 0.5628(3) 0.075(2) 0.0315(10) Uani 0.417(4) 1 d PD C 2
O61B O 0.7319(15) 0.5559(7) 0.106(2) 0.0355(12) Uani 0.417(4) 1 d PD C 2
O62B O 0.8903(9) 0.53142(19) 0.0272(10) 0.0357(7) Uani 0.417(4) 1 d PD C 2
H62B H 0.8496 0.5080 0.0291 0.043 Uiso 0.417(4) 1 calc PR C 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N11 C16 1.364(2) . ?
N11 C12 1.3698(19) . ?
N11 O11 1.3916(17) . ?
O11 H11 0.95(2) . ?
C12 N12 1.325(2) . ?
C12 N13 1.352(2) . ?
N12 H12A 0.84(3) . ?
N12 H12B 0.87(3) . ?
N13 C14 1.376(2) . ?
C14 N21B 1.31(2) . ?
C14 N21A 1.373(12) . ?
C14 C15 1.375(2) . ?
C15 C16 1.337(2) . ?
C15 H15 0.9500 . ?
C16 N16 1.334(2) . ?
N16 H16A 0.83(2) . ?
N16 H16B 0.88(2) . ?
N21A C26A 1.443(8) . ?
N21A C22A 1.473(7) . ?
C22A C23A 1.514(7) . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C23A C24A 1.512(6) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.529(6) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.517(7) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
N21B C26B 1.465(12) . ?
N21B C22B 1.483(12) . ?
C22B C23B 1.511(12) . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C23B C24B 1.528(10) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.532(9) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.516(12) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C31A C36A 1.418(3) . ?
C31A C40A 1.418(3) . ?
C31A C32A 1.431(3) . ?
C32A O32A 1.348(2) . ?
C32A C33A 1.389(3) . ?
O32A H32A 0.8400 . ?
C33A C34A 1.420(3) . ?
C33A C41A 1.479(3) . ?
C34A C35A 1.361(4) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.416(3) . ?
C35A H35A 0.9500 . ?
C36A C37A 1.423(4) . ?
C37A C38A 1.361(4) . ?
C37A H37A 0.9500 . ?
C38A C39A 1.405(4) . ?
C38A H38A 0.9500 . ?
C39A C40A 1.371(4) . ?
C39A H39A 0.9500 . ?
C40A H40A 0.9500 . ?
C41A O42A 1.260(3) . ?
C41A O41A 1.285(2) . ?
C31B C36B 1.417(14) . ?
C31B C40B 1.420(14) . ?
C31B C32B 1.447(14) . ?
C32B O32B 1.327(14) . ?
C32B C33B 1.393(14) . ?
O32B H32B 0.8400 . ?
C33B C34B 1.419(14) . ?
C33B C41B 1.469(14) . ?
C34B C35B 1.353(15) . ?
C34B H34B 0.9500 . ?
C35B C36B 1.417(14) . ?
C35B H35B 0.9500 . ?
C36B C37B 1.419(15) . ?
C37B C38B 1.359(16) . ?
C37B H37B 0.9500 . ?
C38B C39B 1.412(16) . ?
C38B H38B 0.9500 . ?
C39B C40B 1.365(16) . ?
C39B H39B 0.9500 . ?
C40B H40B 0.9500 . ?
C41B O41B 1.267(15) . ?
C41B O42B 1.288(15) . ?
C51A C60A 1.418(6) . ?
C51A C52A 1.431(7) . ?
C51A C56A 1.434(6) . ?
C52A O52A 1.344(7) . ?
C52A C53A 1.398(6) . ?
O52A H52A 0.8400 . ?
C53A C54A 1.427(7) . ?
C53A C61A 1.462(6) . ?
C54A C55A 1.353(5) . ?
C54A H54A 0.9500 . ?
C55A C56A 1.418(5) . ?
C55A H55A 0.9500 . ?
C56A C57A 1.422(6) . ?
C57A C58A 1.363(6) . ?
C57A H57A 0.9500 . ?
C58A C59A 1.411(7) . ?
C58A H58A 0.9500 . ?
C59A C60A 1.368(7) . ?
C59A H59A 0.9500 . ?
C60A H60A 0.9500 . ?
C61A O61A 1.244(7) . ?
C61A O62A 1.306(7) . ?
O62A H62A 0.8400 . ?
C51B C60B 1.401(9) . ?
C51B C56B 1.418(9) . ?
C51B C52B 1.427(10) . ?
C52B O52B 1.346(11) . ?
C52B C53B 1.382(9) . ?
O52B H52B 0.8400 . ?
C53B C54B 1.435(9) . ?
C53B C61B 1.452(9) . ?
C54B C55B 1.353(8) . ?
C54B H54B 0.9500 . ?
C55B C56B 1.410(7) . ?
C55B H55B 0.9500 . ?
C56B C57B 1.431(9) . ?
C57B C58B 1.346(8) . ?
C57B H57B 0.9500 . ?
C58B C59B 1.408(10) . ?
C58B H58B 0.9500 . ?
C59B C60B 1.366(10) . ?
C59B H59B 0.9500 . ?
C60B H60B 0.9500 . ?
C61B O61B 1.265(11) . ?
C61B O62B 1.312(10) . ?
O62B H62B 0.8400 . ?

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
C16 N11 C12 121.47(14) . . ?
C16 N11 O11 119.65(12) . . ?
C12 N11 O11 118.64(13) . . ?
N11 O11 H11 102.3(12) . . ?
N12 C12 N13 124.35(15) . . ?
N12 C12 N11 116.71(16) . . ?
N13 C12 N11 118.94(15) . . ?
C12 N12 H12A 113.7(17) . . ?
C12 N12 H12B 125.9(16) . . ?
H12A N12 H12B 120(2) . . ?
C12 N13 C14 119.28(14) . . ?
N21B C14 C15 113.7(7) . . ?
N21A C14 C15 122.2(4) . . ?
N21B C14 N13 124.9(7) . . ?
N21A C14 N13 116.7(4) . . ?
C15 C14 N13 121.15(15) . . ?
C16 C15 C14 119.08(15) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
N16 C16 C15 123.42(15) . . ?
N16 C16 N11 116.56(15) . . ?
C15 C16 N11 120.02(14) . . ?
C16 N16 H16A 116.9(16) . . ?
C16 N16 H16B 121.1(15) . . ?
H16A N16 H16B 122(2) . . ?
C14 N21A C26A 121.6(7) . . ?
C14 N21A C22A 123.0(8) . . ?
C26A N21A C22A 115.2(8) . . ?
N21A C22A C23A 111.2(6) . . ?
N21A C22A H22A 109.4 . . ?
C23A C22A H22A 109.4 . . ?
N21A C22A H22B 109.4 . . ?
C23A C22A H22B 109.4 . . ?
H22A C22A H22B 108.0 . . ?
C24A C23A C22A 112.3(5) . . ?
C24A C23A H23A 109.1 . . ?
C22A C23A H23A 109.1 . . ?
C24A C23A H23B 109.1 . . ?
C22A C23A H23B 109.1 . . ?
H23A C23A H23B 107.9 . . ?
C23A C24A C25A 109.7(3) . . ?
C23A C24A H24A 109.7 . . ?
C25A C24A H24A 109.7 . . ?
C23A C24A H24B 109.7 . . ?
C25A C24A H24B 109.7 . . ?
H24A C24A H24B 108.2 . . ?
C26A C25A C24A 110.0(4) . . ?
C26A C25A H25A 109.7 . . ?
C24A C25A H25A 109.7 . . ?
C26A C25A H25B 109.7 . . ?
C24A C25A H25B 109.7 . . ?
H25A C25A H25B 108.2 . . ?
N21A C26A C25A 112.8(7) . . ?
N21A C26A H26A 109.0 . . ?
C25A C26A H26A 109.0 . . ?
N21A C26A H26B 109.0 . . ?
C25A C26A H26B 109.0 . . ?
H26A C26A H26B 107.8 . . ?
C14 N21B C26B 126.2(15) . . ?
C14 N21B C22B 120.1(14) . . ?
C26B N21B C22B 112.3(13) . . ?
N21B C22B C23B 108.3(13) . . ?
N21B C22B H22C 110.0 . . ?
C23B C22B H22C 110.0 . . ?
N21B C22B H22D 110.0 . . ?
C23B C22B H22D 110.0 . . ?
H22C C22B H22D 108.4 . . ?
C22B C23B C24B 110.1(8) . . ?
C22B C23B H23C 109.6 . . ?
C24B C23B H23C 109.6 . . ?
C22B C23B H23D 109.6 . . ?
C24B C23B H23D 109.6 . . ?
H23C C23B H23D 108.2 . . ?
C23B C24B C25B 111.0(6) . . ?
C23B C24B H24C 109.4 . . ?
C25B C24B H24C 109.4 . . ?
C23B C24B H24D 109.4 . . ?
C25B C24B H24D 109.4 . . ?
H24C C24B H24D 108.0 . . ?
C26B C25B C24B 110.8(7) . . ?
C26B C25B H25C 109.5 . . ?
C24B C25B H25C 109.5 . . ?
C26B C25B H25D 109.5 . . ?
C24B C25B H25D 109.5 . . ?
H25C C25B H25D 108.1 . . ?
N21B C26B C25B 106.6(14) . . ?
N21B C26B H26C 110.4 . . ?
C25B C26B H26C 110.4 . . ?
N21B C26B H26D 110.4 . . ?
C25B C26B H26D 110.4 . . ?
H26C C26B H26D 108.6 . . ?
C36A C31A C40A 119.1(2) . . ?
C36A C31A C32A 119.0(2) . . ?
C40A C31A C32A 121.86(18) . . ?
O32A C32A C33A 122.48(19) . . ?
O32A C32A C31A 117.02(17) . . ?
C33A C32A C31A 120.49(16) . . ?
C32A O32A H32A 109.5 . . ?
C32A C33A C34A 118.9(2) . . ?
C32A C33A C41A 121.69(17) . . ?
C34A C33A C41A 119.32(19) . . ?
C35A C34A C33A 121.7(2) . . ?
C35A C34A H34A 119.1 . . ?
C33A C34A H34A 119.1 . . ?
C34A C35A C36A 120.36(18) . . ?
C34A C35A H35A 119.8 . . ?
C36A C35A H35A 119.8 . . ?
C35A C36A C31A 119.5(2) . . ?
C35A C36A C37A 122.4(2) . . ?
C31A C36A C37A 118.1(2) . . ?
C38A C37A C36A 121.6(2) . . ?
C38A C37A H37A 119.2 . . ?
C36A C37A H37A 119.2 . . ?
C37A C38A C39A 120.1(3) . . ?
C37A C38A H38A 120.0 . . ?
C39A C38A H38A 120.0 . . ?
C40A C39A C38A 120.3(3) . . ?
C40A C39A H39A 119.8 . . ?
C38A C39A H39A 119.8 . . ?
C39A C40A C31A 120.8(2) . . ?
C39A C40A H40A 119.6 . . ?
C31A C40A H40A 119.6 . . ?
O42A C41A O41A 122.5(2) . . ?
O42A C41A C33A 119.4(2) . . ?
O41A C41A C33A 118.11(18) . . ?
C36B C31B C40B 118.8(15) . . ?
C36B C31B C32B 122.3(14) . . ?
C40B C31B C32B 118.9(15) . . ?
O32B C32B C33B 123.5(18) . . ?
O32B C32B C31B 118.5(18) . . ?
C33B C32B C31B 117.9(14) . . ?
C32B O32B H32B 109.5 . . ?
C32B C33B C34B 116.9(15) . . ?
C32B C33B C41B 122.6(15) . . ?
C34B C33B C41B 120.0(15) . . ?
C35B C34B C33B 125.2(18) . . ?
C35B C34B H34B 117.4 . . ?
C33B C34B H34B 117.4 . . ?
C34B C35B C36B 118.5(17) . . ?
C34B C35B H35B 120.7 . . ?
C36B C35B H35B 120.7 . . ?
C35B C36B C31B 117.6(15) . . ?
C35B C36B C37B 123.6(17) . . ?
C31B C36B C37B 118.7(15) . . ?
C38B C37B C36B 120(2) . . ?
C38B C37B H37B 119.8 . . ?
C36B C37B H37B 119.8 . . ?
C37B C38B C39B 120(2) . . ?
C37B C38B H38B 120.0 . . ?
C39B C38B H38B 120.0 . . ?
C40B C39B C38B 120(2) . . ?
C40B C39B H39B 120.1 . . ?
C38B C39B H39B 120.1 . . ?
C39B C40B C31B 120.7(18) . . ?
C39B C40B H40B 119.6 . . ?
C31B C40B H40B 119.6 . . ?
O41B C41B O42B 122(2) . . ?
O41B C41B C33B 118(2) . . ?
O42B C41B C33B 120.3(19) . . ?
C60A C51A C52A 122.0(5) . . ?
C60A C51A C56A 119.7(5) . . ?
C52A C51A C56A 118.4(4) . . ?
O52A C52A C53A 122.0(7) . . ?
O52A C52A C51A 117.1(7) . . ?
C53A C52A C51A 120.8(6) . . ?
C52A O52A H52A 109.5 . . ?
C52A C53A C54A 118.8(5) . . ?
C52A C53A C61A 119.4(6) . . ?
C54A C53A C61A 121.7(5) . . ?
C55A C54A C53A 121.6(4) . . ?
C55A C54A H54A 119.2 . . ?
C53A C54A H54A 119.2 . . ?
C54A C55A C56A 120.9(4) . . ?
C54A C55A H55A 119.5 . . ?
C56A C55A H55A 119.5 . . ?
C55A C56A C57A 123.2(4) . . ?
C55A C56A C51A 119.5(4) . . ?
C57A C56A C51A 117.3(4) . . ?
C58A C57A C56A 121.8(5) . . ?
C58A C57A H57A 119.1 . . ?
C56A C57A H57A 119.1 . . ?
C57A C58A C59A 120.4(5) . . ?
C57A C58A H58A 119.8 . . ?
C59A C58A H58A 119.8 . . ?
C60A C59A C58A 120.2(5) . . ?
C60A C59A H59A 119.9 . . ?
C58A C59A H59A 119.9 . . ?
C59A C60A C51A 120.6(5) . . ?
C59A C60A H60A 119.7 . . ?
C51A C60A H60A 119.7 . . ?
O61A C61A O62A 121.9(7) . . ?
O61A C61A C53A 122.1(8) . . ?
O62A C61A C53A 116.0(5) . . ?
C61A O62A H62A 109.5 . . ?
C60B C51B C56B 120.3(8) . . ?
C60B C51B C52B 121.4(8) . . ?
C56B C51B C52B 118.3(7) . . ?
O52B C52B C53B 123.4(10) . . ?
O52B C52B C51B 114.8(10) . . ?
C53B C52B C51B 121.7(9) . . ?
C52B O52B H52B 109.5 . . ?
C52B C53B C54B 117.9(8) . . ?
C52B C53B C61B 120.3(9) . . ?
C54B C53B C61B 121.7(8) . . ?
C55B C54B C53B 121.5(6) . . ?
C55B C54B H54B 119.3 . . ?
C53B C54B H54B 119.3 . . ?
C54B C55B C56B 120.9(6) . . ?
C54B C55B H55B 119.5 . . ?
C56B C55B H55B 119.5 . . ?
C55B C56B C51B 119.6(6) . . ?
C55B C56B C57B 122.8(7) . . ?
C51B C56B C57B 117.5(6) . . ?
C58B C57B C56B 120.9(8) . . ?
C58B C57B H57B 119.6 . . ?
C56B C57B H57B 119.6 . . ?
C57B C58B C59B 120.8(8) . . ?
C57B C58B H58B 119.6 . . ?
C59B C58B H58B 119.6 . . ?
C60B C59B C58B 120.4(7) . . ?
C60B C59B H59B 119.8 . . ?
C58B C59B H59B 119.8 . . ?
C59B C60B C51B 120.0(8) . . ?
C59B C60B H60B 120.0 . . ?
C51B C60B H60B 120.0 . . ?
O61B C61B O62B 120.9(11) . . ?
O61B C61B C53B 122.6(12) . . ?
O62B C61B C53B 116.3(8) . . ?
C61B O62B H62B 109.5 . . ?

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
C16 N11 C12 N12 -178.39(15) . . . . ?
O11 N11 C12 N12 -4.1(2) . . . . ?
C16 N11 C12 N13 1.7(2) . . . . ?
O11 N11 C12 N13 176.02(14) . . . . ?
N12 C12 N13 C14 179.48(17) . . . . ?
N11 C12 N13 C14 -0.7(2) . . . . ?
C12 N13 C14 N21B -173.1(16) . . . . ?
C12 N13 C14 N21A 178.4(9) . . . . ?
C12 N13 C14 C15 0.7(3) . . . . ?
N21B C14 C15 C16 172.7(14) . . . . ?
N21A C14 C15 C16 -179.3(9) . . . . ?
N13 C14 C15 C16 -1.8(3) . . . . ?
C14 C15 C16 N16 -177.82(16) . . . . ?
C14 C15 C16 N11 2.8(2) . . . . ?
C12 N11 C16 N16 177.73(15) . . . . ?
O11 N11 C16 N16 3.5(2) . . . . ?
C12 N11 C16 C15 -2.9(2) . . . . ?
O11 N11 C16 C15 -177.08(14) . . . . ?
C15 C14 N21A C26A -9.7(18) . . . . ?
N13 C14 N21A C26A 172.6(10) . . . . ?
C15 C14 N21A C22A 175.0(9) . . . . ?
N13 C14 N21A C22A -2.6(17) . . . . ?
C14 N21A C22A C23A -133.9(13) . . . . ?
C26A N21A C22A C23A 50.6(14) . . . . ?
N21A C22A C23A C24A -52.1(10) . . . . ?
C22A C23A C24A C25A 55.8(6) . . . . ?
C23A C24A C25A C26A -55.7(7) . . . . ?
C14 N21A C26A C25A 131.8(12) . . . . ?
C22A N21A C26A C25A -52.6(15) . . . . ?
C24A C25A C26A N21A 54.4(10) . . . . ?
C15 C14 N21B C26B 10(3) . . . . ?
N13 C14 N21B C26B -176.1(16) . . . . ?
C15 C14 N21B C22B 175.1(16) . . . . ?
N13 C14 N21B C22B -11(3) . . . . ?
C14 N21B C22B C23B -102(2) . . . . ?
C26B N21B C22B C23B 65(2) . . . . ?
N21B C22B C23B C24B -56.5(15) . . . . ?
C22B C23B C24B C25B 53.2(11) . . . . ?
C23B C24B C25B C26B -54.8(12) . . . . ?
C14 N21B C26B C25B 101(2) . . . . ?
C22B N21B C26B C25B -65(2) . . . . ?
C24B C25B C26B N21B 58.8(16) . . . . ?
C36A C31A C32A O32A -179.06(17) . . . . ?
C40A C31A C32A O32A 0.1(3) . . . . ?
C36A C31A C32A C33A 0.5(3) . . . . ?
C40A C31A C32A C33A 179.62(19) . . . . ?
O32A C32A C33A C34A 179.79(19) . . . . ?
C31A C32A C33A C34A 0.3(3) . . . . ?
O32A C32A C33A C41A 2.5(3) . . . . ?
C31A C32A C33A C41A -177.02(18) . . . . ?
C32A C33A C34A C35A -0.9(3) . . . . ?
C41A C33A C34A C35A 176.5(2) . . . . ?
C33A C34A C35A C36A 0.7(4) . . . . ?
C34A C35A C36A C31A 0.1(3) . . . . ?
C34A C35A C36A C37A 179.4(3) . . . . ?
C40A C31A C36A C35A -179.82(19) . . . . ?
C32A C31A C36A C35A -0.6(3) . . . . ?
C40A C31A C36A C37A 0.8(3) . . . . ?
C32A C31A C36A C37A -180.0(3) . . . . ?
C35A C36A C37A C38A 179.7(4) . . . . ?
C31A C36A C37A C38A -1.0(6) . . . . ?
C36A C37A C38A C39A 0.7(8) . . . . ?
C37A C38A C39A C40A -0.4(7) . . . . ?
C38A C39A C40A C31A 0.3(5) . . . . ?
C36A C31A C40A C39A -0.5(4) . . . . ?
C32A C31A C40A C39A -179.7(3) . . . . ?
C32A C33A C41A O42A 171.4(2) . . . . ?
C34A C33A C41A O42A -5.9(3) . . . . ?
C32A C33A C41A O41A -8.1(3) . . . . ?
C34A C33A C41A O41A 174.7(2) . . . . ?
C36B C31B C32B O32B -179(4) . . . . ?
C40B C31B C32B O32B 3(5) . . . . ?
C36B C31B C32B C33B 1(5) . . . . ?
C40B C31B C32B C33B -177(3) . . . . ?
O32B C32B C33B C34B 170(3) . . . . ?
C31B C32B C33B C34B -9(4) . . . . ?
O32B C32B C33B C41B -2(5) . . . . ?
C31B C32B C33B C41B 178(3) . . . . ?
C32B C33B C34B C35B 16(6) . . . . ?
C41B C33B C34B C35B -172(4) . . . . ?
C33B C34B C35B C36B -12(6) . . . . ?
C34B C35B C36B C31B 2(6) . . . . ?
C34B C35B C36B C37B -178(5) . . . . ?
C40B C31B C36B C35B -179(3) . . . . ?
C32B C31B C36B C35B 4(6) . . . . ?
C40B C31B C36B C37B 1(6) . . . . ?
C32B C31B C36B C37B -177(4) . . . . ?
C35B C36B C37B C38B 171(8) . . . . ?
C31B C36B C37B C38B -8(10) . . . . ?
C36B C37B C38B C39B 15(15) . . . . ?
C37B C38B C39B C40B -15(16) . . . . ?
C38B C39B C40B C31B 7(11) . . . . ?
C36B C31B C40B C39B 0(7) . . . . ?
C32B C31B C40B C39B 177(5) . . . . ?
C32B C33B C41B O41B -2(6) . . . . ?
C34B C33B C41B O41B -174(5) . . . . ?
C32B C33B C41B O42B -178(4) . . . . ?
C34B C33B C41B O42B 10(6) . . . . ?
C60A C51A C52A O52A -2(2) . . . . ?
C56A C51A C52A O52A 178.4(15) . . . . ?
C60A C51A C52A C53A -177.5(12) . . . . ?
C56A C51A C52A C53A 2.5(18) . . . . ?
O52A C52A C53A C54A -177.6(16) . . . . ?
C51A C52A C53A C54A -1.9(19) . . . . ?
O52A C52A C53A C61A 0(2) . . . . ?
C51A C52A C53A C61A 176.0(12) . . . . ?
C52A C53A C54A C55A -0.1(15) . . . . ?
C61A C53A C54A C55A -178.0(9) . . . . ?
C53A C54A C55A C56A 1.4(11) . . . . ?
C54A C55A C56A C57A 178.6(6) . . . . ?
C54A C55A C56A C51A -0.7(9) . . . . ?
C60A C51A C56A C55A 178.8(8) . . . . ?
C52A C51A C56A C55A -1.2(13) . . . . ?
C60A C51A C56A C57A -0.5(12) . . . . ?
C52A C51A C56A C57A 179.5(9) . . . . ?
C55A C56A C57A C58A -179.2(6) . . . . ?
C51A C56A C57A C58A 0.1(10) . . . . ?
C56A C57A C58A C59A 0.4(10) . . . . ?
C57A C58A C59A C60A -0.4(13) . . . . ?
C58A C59A C60A C51A -0.1(15) . . . . ?
C52A C51A C60A C59A -179.5(12) . . . . ?
C56A C51A C60A C59A 0.6(16) . . . . ?
C52A C53A C61A O61A 9(2) . . . . ?
C54A C53A C61A O61A -172.7(13) . . . . ?
C52A C53A C61A O62A -173.7(12) . . . . ?
C54A C53A C61A O62A 4.2(17) . . . . ?
C60B C51B C52B O52B 4(3) . . . . ?
C56B C51B C52B O52B -178(2) . . . . ?
C60B C51B C52B C53B -179.6(19) . . . . ?
C56B C51B C52B C53B -2(3) . . . . ?
O52B C52B C53B C54B 179(2) . . . . ?
C51B C52B C53B C54B 3(3) . . . . ?
O52B C52B C53B C61B -4(4) . . . . ?
C51B C52B C53B C61B -179.8(18) . . . . ?
C52B C53B C54B C55B -1(2) . . . . ?
C61B C53B C54B C55B -179.0(14) . . . . ?
C53B C54B C55B C56B -0.9(16) . . . . ?
C54B C55B C56B C51B 2.0(15) . . . . ?
C54B C55B C56B C57B 179.2(9) . . . . ?
C60B C51B C56B C55B 177.3(13) . . . . ?
C52B C51B C56B C55B -1(2) . . . . ?
C60B C51B C56B C57B -0.1(18) . . . . ?
C52B C51B C56B C57B -178.2(14) . . . . ?
C55B C56B C57B C58B -178.4(10) . . . . ?
C51B C56B C57B C58B -1.1(16) . . . . ?
C56B C57B C58B C59B 2.8(17) . . . . ?
C57B C58B C59B C60B -3(2) . . . . ?
C58B C59B C60B C51B 2(2) . . . . ?
C56B C51B C60B C59B -1(2) . . . . ?
C52B C51B C60B C59B 177.6(18) . . . . ?
C52B C53B C61B O61B 3(3) . . . . ?
C54B C53B C61B O61B -180(2) . . . . ?
C52B C53B C61B O62B -172.3(19) . . . . ?
C54B C53B C61B O62B 5(3) . . . . ?

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
O11 H11 O42A 0.95(2) 1.64(2) 2.584(2) 175.1(19) .
O11 H11 O41B 0.95(2) 1.90(5) 2.84(5) 173(2) .
O52A H52A O61A 0.84 1.82 2.561(17) 146.6 .
O52B H52B O61B 0.84 1.92 2.61(3) 138.2 .
O62A H62A O41A 0.84 1.57 2.401(4) 172.5 .
O62A H62A O42B 0.84 1.08 1.91(3) 164.3 .
O62B H62B O41A 0.84 2.00 2.834(5) 172.1 .
O62B H62B O42B 0.84 1.51 2.34(3) 174.5 .
N12 H12A O62B 0.84(3) 2.46(3) 2.977(9) 121(2) 3_766
N12 H12B O42A 0.87(3) 2.00(3) 2.860(3) 170(2) 3_766
N12 H12B O41B 0.87(3) 2.07(5) 2.92(5) 168(3) 3_766
N16 H16A O61A 0.83(2) 2.24(3) 3.033(10) 160(2) 3_665
N16 H16A O61B 0.83(2) 2.52(3) 3.311(15) 161(2) 3_665
N16 H16B O61A 0.88(2) 2.07(3) 2.904(11) 158(2) .
N16 H16B O61B 0.88(2) 2.20(3) 3.064(15) 165(2) .

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        32.75
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045

# Attachment '_8__cif1.cif'

data_ns0810m
_database_code_depnum_ccdc_archive 'CCDC 733882'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3262-11-02 minoxidil : 1-hydroxy-2-naphthoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O)2 (C11 H8 O3) (H2 O)0.5
;
_chemical_formula_sum            'C29 H39 N10 O5.50'
_chemical_formula_weight         615.70

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6564(5)
_cell_length_b                   12.4660(7)
_cell_length_c                   13.9860(8)
_cell_angle_alpha                107.291(3)
_cell_angle_beta                 96.977(3)
_cell_angle_gamma                107.027(3)
_cell_volume                     1496.42(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8137
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      31.35

_exptl_crystal_description       prism
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             654
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30989
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         31.45
_reflns_number_total             9753
_reflns_number_gt                6056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0650P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9753
_refine_ls_number_parameters     545
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1641
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1S O 0.0821(4) 0.5098(3) 0.5004(3) 0.0615(7) Uani 0.50 1 d P . .
H1A H 0.048(5) 0.534(4) 0.439(4) 0.074 Uiso 0.50 1 d P . .
H1B H 0.006(9) 0.528(5) 0.539(4) 0.074 Uiso 0.50 1 d P . .
N11_1 N 0.57331(13) 0.59406(10) 0.73279(9) 0.0327(2) Uani 1 1 d . A .
O11_1 O 0.60089(12) 0.68611(9) 0.69453(9) 0.0413(3) Uani 1 1 d . . .
H11_1 H 0.6031(19) 0.6434(15) 0.6061(14) 0.050 Uiso 1 1 d . . .
C12_1 C 0.43243(15) 0.54208(12) 0.74292(10) 0.0327(3) Uani 1 1 d . . .
N12_1 N 0.32940(15) 0.58420(13) 0.71223(11) 0.0432(3) Uani 1 1 d . A .
H12A_1 H 0.229(2) 0.5519(16) 0.7161(14) 0.052 Uiso 1 1 d . . .
H12B_1 H 0.360(2) 0.6425(17) 0.6878(14) 0.052 Uiso 1 1 d . . .
N13_1 N 0.40520(14) 0.45365(11) 0.78300(10) 0.0331(3) Uani 0.461(13) 1 d P A 1
C13_1 C 0.40520(14) 0.45365(11) 0.78300(10) 0.0331(3) Uani 0.539(13) 1 d P A 2
H13_1 H 0.3077 0.4164 0.7898 0.040 Uiso 0.539(13) 1 calc PR A 2
C14_1 C 0.52010(15) 0.41826(11) 0.81385(10) 0.0305(3) Uani 1 1 d . . .
C15_1 C 0.66003(14) 0.46750(11) 0.79995(10) 0.0344(3) Uani 0.461(13) 1 d P A 1
H15A_1 H 0.7379 0.4403 0.8186 0.041 Uiso 0.461(13) 1 calc PR A 1
N15_1 N 0.66003(14) 0.46750(11) 0.79995(10) 0.0344(3) Uani 0.539(13) 1 d P A 2
C16_1 C 0.68501(16) 0.55484(13) 0.75947(12) 0.0368(3) Uani 1 1 d . . .
N16_1 N 0.81868(16) 0.60987(14) 0.74537(14) 0.0523(4) Uani 1 1 d . A .
H16A_1 H 0.887(2) 0.5764(19) 0.7482(16) 0.063 Uiso 1 1 d . . .
H16B_1 H 0.824(2) 0.6571(19) 0.7101(16) 0.063 Uiso 1 1 d . . .
N21_1 N 0.49696(13) 0.33552(11) 0.85964(10) 0.0348(3) Uani 1 1 d . A .
C22_1 C 0.35007(15) 0.27417(13) 0.87320(11) 0.0357(3) Uani 1 1 d . . .
H22A_1 H 0.3103 0.1907 0.8240 0.043 Uiso 1 1 calc R A .
H22B_1 H 0.2809 0.3152 0.8585 0.043 Uiso 1 1 calc R . .
C23_1 C 0.35978(16) 0.27363(13) 0.98249(11) 0.0373(3) Uani 1 1 d . A .
H23A_1 H 0.3855 0.3566 1.0307 0.045 Uiso 1 1 calc R . .
H23B_1 H 0.2614 0.2254 0.9880 0.045 Uiso 1 1 calc R . .
C24_1 C 0.47546(18) 0.22232(15) 1.01292(12) 0.0431(4) Uani 1 1 d . . .
H24A_1 H 0.4436 0.1362 0.9709 0.052 Uiso 1 1 calc R A .
H24B_1 H 0.4851 0.2298 1.0861 0.052 Uiso 1 1 calc R . .
C25_1 C 0.62506(18) 0.28924(16) 0.99657(13) 0.0455(4) Uani 1 1 d . A .
H25A_1 H 0.6620 0.3733 1.0445 0.055 Uiso 1 1 calc R . .
H25B_1 H 0.6982 0.2516 1.0118 0.055 Uiso 1 1 calc R . .
C26_1 C 0.61077(17) 0.28701(15) 0.88633(13) 0.0421(4) Uani 1 1 d . . .
H26A_1 H 0.7075 0.3350 0.8784 0.050 Uiso 1 1 calc R A .
H26B_1 H 0.5841 0.2036 0.8388 0.050 Uiso 1 1 calc R . .
N11_2 N 0.63039(17) 0.69315(11) 0.47963(10) 0.0475(3) Uani 1 1 d . B .
O11_2 O 0.61014(17) 0.60065(10) 0.51709(12) 0.0647(4) Uani 1 1 d . . .
C12_2 C 0.7663(2) 0.74361(13) 0.46309(14) 0.0502(4) Uani 1 1 d . . .
N12_2 N 0.8705(2) 0.70180(14) 0.49085(18) 0.0719(6) Uani 1 1 d . B .
H12A_2 H 0.951(3) 0.719(2) 0.4680(19) 0.086 Uiso 1 1 d . . .
H12B_2 H 0.843(3) 0.634(2) 0.5083(19) 0.086 Uiso 1 1 d . . .
N13_2 N 0.78936(17) 0.83117(12) 0.42331(11) 0.0464(4) Uani 0.696(16) 1 d P B 1
C13_2 C 0.78936(17) 0.83117(12) 0.42331(11) 0.0464(4) Uani 0.304(16) 1 d P B 2
H13_2 H 0.8842 0.8664 0.4115 0.056 Uiso 0.304(16) 1 calc PR B 2
C14_2 C 0.67546(19) 0.86855(14) 0.40015(11) 0.0443(4) Uani 1 1 d . . .
C15_2 C 0.53466(19) 0.81645(16) 0.41471(11) 0.0518(5) Uani 0.696(16) 1 d P B 1
H15_2 H 0.4555 0.8432 0.3979 0.062 Uiso 0.696(16) 1 calc PR B 1
N15_2 N 0.53466(19) 0.81645(16) 0.41471(11) 0.0518(5) Uani 0.304(16) 1 d P B 2
C16_2 C 0.5131(2) 0.72568(16) 0.45385(11) 0.0491(4) Uani 1 1 d . . .
N16_2 N 0.38460(18) 0.66605(18) 0.47240(12) 0.0610(5) Uani 1 1 d . B .
H16A_2 H 0.380(3) 0.600(2) 0.4952(17) 0.073 Uiso 1 1 d . . .
H16B_2 H 0.304(3) 0.683(2) 0.4471(18) 0.073 Uiso 1 1 d . . .
N21_2 N 0.70237(15) 0.95744(12) 0.35880(10) 0.0444(3) Uani 1 1 d . B .
C22_2 C 0.85786(19) 1.02078(16) 0.35946(14) 0.0504(4) Uani 1 1 d . . .
H22A_2 H 0.9113 0.9631 0.3458 0.061 Uiso 1 1 calc R B .
H22B_2 H 0.9076 1.0823 0.4284 0.061 Uiso 1 1 calc R . .
C23_2 C 0.8664(2) 1.08060(16) 0.27875(16) 0.0573(5) Uani 1 1 d . B .
H23A_2 H 0.9713 1.1292 0.2865 0.069 Uiso 1 1 calc R . .
H23B_2 H 0.8319 1.0180 0.2094 0.069 Uiso 1 1 calc R . .
C24_2 C 0.7732(2) 1.15999(17) 0.28780(17) 0.0616(5) Uani 1 1 d . . .
H24A_2 H 0.7774 1.1937 0.2320 0.074 Uiso 1 1 calc R B .
H24B_2 H 0.8125 1.2273 0.3545 0.074 Uiso 1 1 calc R . .
C25_2 C 0.6137(2) 1.08680(17) 0.28037(16) 0.0578(4) Uani 1 1 d . B .
H25A_2 H 0.5722 1.0244 0.2111 0.069 Uiso 1 1 calc R . .
H25B_2 H 0.5534 1.1395 0.2897 0.069 Uiso 1 1 calc R . .
C26_2 C 0.6034(2) 1.02735(17) 0.36138(14) 0.0526(4) Uani 1 1 d . . .
H26A_2 H 0.6296 1.0898 0.4304 0.063 Uiso 1 1 calc R B .
H26B_2 H 0.4995 0.9739 0.3497 0.063 Uiso 1 1 calc R . .
C31A_3 C 0.1229(4) 0.8646(2) 0.1727(2) 0.0387(6) Uani 0.670(2) 1 d PD C 1
C32A_3 C 0.1191(2) 0.8162(2) 0.25402(18) 0.0389(5) Uani 0.670(2) 1 d PD C 1
O32A_3 O 0.1877(3) 0.8947(2) 0.34962(16) 0.0543(6) Uani 0.670(2) 1 d PD C 1
H32A_3 H 0.177(5) 0.845(4) 0.383(3) 0.065 Uiso 0.670(2) 1 d P C 1
C33A_3 C 0.0485(5) 0.6951(3) 0.2321(2) 0.0369(6) Uani 0.670(2) 1 d PD C 1
C34A_3 C -0.0206(4) 0.6187(3) 0.1294(3) 0.0361(7) Uani 0.670(2) 1 d PD C 1
H34A_3 H -0.0690 0.5354 0.1146 0.043 Uiso 0.670(2) 1 calc PR C 1
C35A_3 C -0.0181(2) 0.6638(2) 0.05111(16) 0.0362(5) Uani 0.670(2) 1 d PD C 1
H35A_3 H -0.0658 0.6121 -0.0177 0.043 Uiso 0.670(2) 1 calc PR C 1
C36A_3 C 0.0555(3) 0.7874(3) 0.0729(2) 0.0347(5) Uani 0.670(2) 1 d PD C 1
C37A_3 C 0.0657(7) 0.8368(3) -0.0068(3) 0.0519(8) Uani 0.670(2) 1 d PD C 1
H37A_3 H 0.0192 0.7854 -0.0759 0.062 Uiso 0.670(2) 1 calc PR C 1
C38A_3 C 0.1396(7) 0.9549(3) 0.0123(3) 0.0505(9) Uani 0.670(2) 1 d PD C 1
H38A_3 H 0.1474 0.9852 -0.0423 0.061 Uiso 0.670(2) 1 calc PR C 1
C39A_3 C 0.2049(4) 1.0318(3) 0.1161(3) 0.0538(8) Uani 0.670(2) 1 d PD C 1
H39A_3 H 0.2546 1.1147 0.1306 0.065 Uiso 0.670(2) 1 calc PR C 1
C40A_3 C 0.1981(4) 0.9895(3) 0.1954(3) 0.0495(8) Uani 0.670(2) 1 d PD C 1
H40A_3 H 0.2424 1.0420 0.2644 0.059 Uiso 0.670(2) 1 calc PR C 1
C41A_3 C 0.0484(7) 0.6455(4) 0.3172(3) 0.0453(9) Uani 0.670(2) 1 d PD C 1
O41A_3 O 0.1208(2) 0.7200(3) 0.40821(15) 0.0611(6) Uani 0.670(2) 1 d PD C 1
O42A_3 O -0.0136(2) 0.5352(2) 0.2969(2) 0.0517(5) Uani 0.670(2) 1 d PD C 1
C31B_3 C 0.0678(6) 0.7912(5) 0.1206(4) 0.0380(12) Uani 0.330(2) 1 d PD C 2
C32B_3 C 0.0260(5) 0.6943(4) 0.1600(3) 0.0383(11) Uani 0.330(2) 1 d PD C 2
O32B_3 O -0.0532(6) 0.5851(4) 0.0909(3) 0.0413(12) Uani 0.330(2) 1 d PD C 2
H32B_3 H -0.065(6) 0.532(5) 0.135(4) 0.050 Uiso 0.330(2) 1 d P C 2
C33B_3 C 0.0739(11) 0.7140(5) 0.2629(4) 0.0369(6) Uani 0.330(2) 1 d PD C 2
C34B_3 C 0.1590(8) 0.8320(5) 0.3308(5) 0.066(3) Uani 0.330(2) 1 d PD C 2
H34B_3 H 0.1925 0.8463 0.4017 0.079 Uiso 0.330(2) 1 calc PR C 2
C35B_3 C 0.1935(6) 0.9260(4) 0.2948(4) 0.069(2) Uani 0.330(2) 1 d PD C 2
H35B_3 H 0.2458 1.0053 0.3416 0.083 Uiso 0.330(2) 1 calc PR C 2
C36B_3 C 0.1516(10) 0.9051(5) 0.1890(5) 0.0387(6) Uani 0.330(2) 1 d PD C 2
C37B_3 C 0.1969(9) 0.9997(6) 0.1488(6) 0.066(3) Uani 0.330(2) 1 d PD C 2
H37B_3 H 0.2559 1.0783 0.1940 0.080 Uiso 0.330(2) 1 calc PR C 2
C38B_3 C 0.1564(16) 0.9782(7) 0.0469(6) 0.0505(9) Uani 0.330(2) 1 d PD C 2
H38B_3 H 0.1854 1.0418 0.0211 0.061 Uiso 0.330(2) 1 calc PR C 2
C39B_3 C 0.0708(17) 0.8605(7) -0.0215(6) 0.0519(8) Uani 0.330(2) 1 d PD C 2
H39B_3 H 0.0435 0.8463 -0.0930 0.062 Uiso 0.330(2) 1 calc PR C 2
C40B_3 C 0.0270(6) 0.7675(5) 0.0131(5) 0.0492(14) Uani 0.330(2) 1 d PD C 2
H40B_3 H -0.0294 0.6888 -0.0333 0.059 Uiso 0.330(2) 1 calc PR C 2
C41B_3 C 0.0476(15) 0.6110(6) 0.3013(5) 0.0453(9) Uani 0.330(2) 1 d PD C 2
O41B_3 O -0.0366(4) 0.5058(4) 0.2391(3) 0.0443(10) Uani 0.330(2) 1 d PD C 2
O42B_3 O 0.0992(4) 0.6362(4) 0.3954(3) 0.0522(10) Uani 0.330(2) 1 d PD C 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
O1S H1A 1.04(5) . ?
O1S H1B 1.00(7) . ?
N11_1 C16_1 1.3643(18) . ?
N11_1 C12_1 1.3696(18) . ?
N11_1 O11_1 1.3764(14) . ?
O11_1 H11_1 1.198(18) . ?
C12_1 N12_1 1.3363(19) . ?
C12_1 N13_1 1.3536(18) . ?
N12_1 H12A_1 0.95(2) . ?
N12_1 H12B_1 0.88(2) . ?
N13_1 C14_1 1.3767(19) . ?
C14_1 N21_1 1.3478(16) . ?
C14_1 C15_1 1.3745(18) . ?
C15_1 C16_1 1.3454(18) . ?
C15_1 H15A_1 0.9500 . ?
C16_1 N16_1 1.341(2) . ?
N16_1 H16A_1 0.88(2) . ?
N16_1 H16B_1 0.87(2) . ?
N21_1 C26_1 1.4617(17) . ?
N21_1 C22_1 1.4660(17) . ?
C22_1 C23_1 1.522(2) . ?
C22_1 H22A_1 0.9900 . ?
C22_1 H22B_1 0.9900 . ?
C23_1 C24_1 1.518(2) . ?
C23_1 H23A_1 0.9900 . ?
C23_1 H23B_1 0.9900 . ?
C24_1 C25_1 1.524(2) . ?
C24_1 H24A_1 0.9900 . ?
C24_1 H24B_1 0.9900 . ?
C25_1 C26_1 1.522(2) . ?
C25_1 H25A_1 0.9900 . ?
C25_1 H25B_1 0.9900 . ?
C26_1 H26A_1 0.9900 . ?
C26_1 H26B_1 0.9900 . ?
N11_2 C16_2 1.354(3) . ?
N11_2 C12_2 1.360(2) . ?
N11_2 O11_2 1.3762(18) . ?
O11_2 H11_1 1.219(19) . ?
C12_2 N12_2 1.329(3) . ?
C12_2 N13_2 1.341(2) . ?
N12_2 H12A_2 0.87(3) . ?
N12_2 H12B_2 0.92(3) . ?
N13_2 C14_2 1.355(2) . ?
C14_2 N21_2 1.371(2) . ?
C14_2 C15_2 1.393(2) . ?
C15_2 C16_2 1.372(2) . ?
C15_2 H15_2 0.9500 . ?
C16_2 N16_2 1.346(2) . ?
N16_2 H16A_2 0.95(2) . ?
N16_2 H16B_2 0.92(2) . ?
N21_2 C26_2 1.467(2) . ?
N21_2 C22_2 1.475(2) . ?
C22_2 C23_2 1.524(2) . ?
C22_2 H22A_2 0.9900 . ?
C22_2 H22B_2 0.9900 . ?
C23_2 C24_2 1.510(3) . ?
C23_2 H23A_2 0.9900 . ?
C23_2 H23B_2 0.9900 . ?
C24_2 C25_2 1.515(3) . ?
C24_2 H24A_2 0.9900 . ?
C24_2 H24B_2 0.9900 . ?
C25_2 C26_2 1.525(3) . ?
C25_2 H25A_2 0.9900 . ?
C25_2 H25B_2 0.9900 . ?
C26_2 H26A_2 0.9900 . ?
C26_2 H26B_2 0.9900 . ?
C31A_3 C36A_3 1.383(4) . ?
C31A_3 C40A_3 1.428(4) . ?
C31A_3 C32A_3 1.437(4) . ?
C32A_3 O32A_3 1.346(3) . ?
C32A_3 C33A_3 1.381(4) . ?
O32A_3 H32A_3 0.88(4) . ?
C33A_3 C34A_3 1.413(4) . ?
C33A_3 C41A_3 1.495(3) . ?
C34A_3 C35A_3 1.372(4) . ?
C34A_3 H34A_3 0.9500 . ?
C35A_3 C36A_3 1.414(4) . ?
C35A_3 H35A_3 0.9500 . ?
C36A_3 C37A_3 1.425(4) . ?
C37A_3 C38A_3 1.361(4) . ?
C37A_3 H37A_3 0.9500 . ?
C38A_3 C39A_3 1.421(5) . ?
C38A_3 H38A_3 0.9500 . ?
C39A_3 C40A_3 1.363(4) . ?
C39A_3 H39A_3 0.9500 . ?
C40A_3 H40A_3 0.9500 . ?
C41A_3 O42A_3 1.255(5) . ?
C41A_3 O41A_3 1.293(5) . ?
C31B_3 C36B_3 1.384(5) . ?
C31B_3 C40B_3 1.423(5) . ?
C31B_3 C32B_3 1.447(5) . ?
C32B_3 O32B_3 1.342(4) . ?
C32B_3 C33B_3 1.380(5) . ?
O32B_3 H32B_3 1.03(6) . ?
C33B_3 C34B_3 1.419(6) . ?
C33B_3 C41B_3 1.500(4) . ?
C34B_3 C35B_3 1.379(6) . ?
C34B_3 H32A_3 0.69(4) . ?
C34B_3 H34B_3 0.9500 . ?
C35B_3 C36B_3 1.409(5) . ?
C35B_3 H35B_3 0.9500 . ?
C36B_3 C37B_3 1.433(6) . ?
C37B_3 C38B_3 1.354(6) . ?
C37B_3 H37B_3 0.9500 . ?
C38B_3 C39B_3 1.419(7) . ?
C38B_3 H38B_3 0.9500 . ?
C39B_3 C40B_3 1.362(6) . ?
C39B_3 H39B_3 0.9500 . ?
C40B_3 H40B_3 0.9500 . ?
C41B_3 O42B_3 1.259(6) . ?
C41B_3 O41B_3 1.290(7) . ?

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
H1A O1S H1B 96(5) . . ?
C16_1 N11_1 C12_1 120.64(11) . . ?
C16_1 N11_1 O11_1 120.20(11) . . ?
C12_1 N11_1 O11_1 119.16(11) . . ?
N11_1 O11_1 H11_1 106.5(8) . . ?
N12_1 C12_1 N13_1 124.05(13) . . ?
N12_1 C12_1 N11_1 116.41(12) . . ?
N13_1 C12_1 N11_1 119.54(12) . . ?
C12_1 N12_1 H12A_1 121.1(11) . . ?
C12_1 N12_1 H12B_1 116.3(13) . . ?
H12A_1 N12_1 H12B_1 122.6(17) . . ?
C12_1 N13_1 C14_1 119.37(12) . . ?
N21_1 C14_1 C15_1 119.00(12) . . ?
N21_1 C14_1 N13_1 120.13(12) . . ?
C15_1 C14_1 N13_1 120.87(11) . . ?
C16_1 C15_1 C14_1 118.95(12) . . ?
C16_1 C15_1 H15A_1 120.5 . . ?
C14_1 C15_1 H15A_1 120.5 . . ?
N16_1 C16_1 C15_1 123.03(14) . . ?
N16_1 C16_1 N11_1 116.41(13) . . ?
C15_1 C16_1 N11_1 120.54(13) . . ?
C16_1 N16_1 H16A_1 118.2(14) . . ?
C16_1 N16_1 H16B_1 117.8(14) . . ?
H16A_1 N16_1 H16B_1 119(2) . . ?
C14_1 N21_1 C26_1 122.68(11) . . ?
C14_1 N21_1 C22_1 122.72(11) . . ?
C26_1 N21_1 C22_1 114.03(11) . . ?
N21_1 C22_1 C23_1 110.71(12) . . ?
N21_1 C22_1 H22A_1 109.5 . . ?
C23_1 C22_1 H22A_1 109.5 . . ?
N21_1 C22_1 H22B_1 109.5 . . ?
C23_1 C22_1 H22B_1 109.5 . . ?
H22A_1 C22_1 H22B_1 108.1 . . ?
C24_1 C23_1 C22_1 111.82(11) . . ?
C24_1 C23_1 H23A_1 109.3 . . ?
C22_1 C23_1 H23A_1 109.3 . . ?
C24_1 C23_1 H23B_1 109.3 . . ?
C22_1 C23_1 H23B_1 109.3 . . ?
H23A_1 C23_1 H23B_1 107.9 . . ?
C23_1 C24_1 C25_1 109.91(12) . . ?
C23_1 C24_1 H24A_1 109.7 . . ?
C25_1 C24_1 H24A_1 109.7 . . ?
C23_1 C24_1 H24B_1 109.7 . . ?
C25_1 C24_1 H24B_1 109.7 . . ?
H24A_1 C24_1 H24B_1 108.2 . . ?
C26_1 C25_1 C24_1 110.77(14) . . ?
C26_1 C25_1 H25A_1 109.5 . . ?
C24_1 C25_1 H25A_1 109.5 . . ?
C26_1 C25_1 H25B_1 109.5 . . ?
C24_1 C25_1 H25B_1 109.5 . . ?
H25A_1 C25_1 H25B_1 108.1 . . ?
N21_1 C26_1 C25_1 110.74(11) . . ?
N21_1 C26_1 H26A_1 109.5 . . ?
C25_1 C26_1 H26A_1 109.5 . . ?
N21_1 C26_1 H26B_1 109.5 . . ?
C25_1 C26_1 H26B_1 109.5 . . ?
H26A_1 C26_1 H26B_1 108.1 . . ?
C16_2 N11_2 C12_2 121.94(15) . . ?
C16_2 N11_2 O11_2 119.49(13) . . ?
C12_2 N11_2 O11_2 118.41(16) . . ?
N11_2 O11_2 H11_1 105.1(8) . . ?
N12_2 C12_2 N13_2 124.25(16) . . ?
N12_2 C12_2 N11_2 115.41(16) . . ?
N13_2 C12_2 N11_2 120.33(18) . . ?
C12_2 N12_2 H12A_2 117.6(17) . . ?
C12_2 N12_2 H12B_2 119.2(16) . . ?
H12A_2 N12_2 H12B_2 118(2) . . ?
C12_2 N13_2 C14_2 119.03(14) . . ?
N13_2 C14_2 N21_2 117.56(13) . . ?
N13_2 C14_2 C15_2 121.50(16) . . ?
N21_2 C14_2 C15_2 120.91(17) . . ?
C16_2 C15_2 C14_2 118.41(18) . . ?
C16_2 C15_2 H15_2 120.8 . . ?
C14_2 C15_2 H15_2 120.8 . . ?
N16_2 C16_2 N11_2 115.38(17) . . ?
N16_2 C16_2 C15_2 125.9(2) . . ?
N11_2 C16_2 C15_2 118.70(15) . . ?
C16_2 N16_2 H16A_2 118.8(14) . . ?
C16_2 N16_2 H16B_2 113.7(15) . . ?
H16A_2 N16_2 H16B_2 126(2) . . ?
C14_2 N21_2 C26_2 120.15(13) . . ?
C14_2 N21_2 C22_2 118.03(15) . . ?
C26_2 N21_2 C22_2 115.32(13) . . ?
N21_2 C22_2 C23_2 111.49(15) . . ?
N21_2 C22_2 H22A_2 109.3 . . ?
C23_2 C22_2 H22A_2 109.3 . . ?
N21_2 C22_2 H22B_2 109.3 . . ?
C23_2 C22_2 H22B_2 109.3 . . ?
H22A_2 C22_2 H22B_2 108.0 . . ?
C24_2 C23_2 C22_2 112.28(15) . . ?
C24_2 C23_2 H23A_2 109.1 . . ?
C22_2 C23_2 H23A_2 109.1 . . ?
C24_2 C23_2 H23B_2 109.1 . . ?
C22_2 C23_2 H23B_2 109.1 . . ?
H23A_2 C23_2 H23B_2 107.9 . . ?
C23_2 C24_2 C25_2 109.20(15) . . ?
C23_2 C24_2 H24A_2 109.8 . . ?
C25_2 C24_2 H24A_2 109.8 . . ?
C23_2 C24_2 H24B_2 109.8 . . ?
C25_2 C24_2 H24B_2 109.8 . . ?
H24A_2 C24_2 H24B_2 108.3 . . ?
C24_2 C25_2 C26_2 111.50(17) . . ?
C24_2 C25_2 H25A_2 109.3 . . ?
C26_2 C25_2 H25A_2 109.3 . . ?
C24_2 C25_2 H25B_2 109.3 . . ?
C26_2 C25_2 H25B_2 109.3 . . ?
H25A_2 C25_2 H25B_2 108.0 . . ?
N21_2 C26_2 C25_2 112.18(14) . . ?
N21_2 C26_2 H26A_2 109.2 . . ?
C25_2 C26_2 H26A_2 109.2 . . ?
N21_2 C26_2 H26B_2 109.2 . . ?
C25_2 C26_2 H26B_2 109.2 . . ?
H26A_2 C26_2 H26B_2 107.9 . . ?
C36A_3 C31A_3 C40A_3 121.4(3) . . ?
C36A_3 C31A_3 C32A_3 118.5(2) . . ?
C40A_3 C31A_3 C32A_3 120.0(3) . . ?
O32A_3 C32A_3 C33A_3 123.5(2) . . ?
O32A_3 C32A_3 C31A_3 116.3(2) . . ?
C33A_3 C32A_3 C31A_3 120.2(2) . . ?
C32A_3 O32A_3 H32A_3 99(3) . . ?
C32A_3 C33A_3 C34A_3 119.9(2) . . ?
C32A_3 C33A_3 C41A_3 119.6(3) . . ?
C34A_3 C33A_3 C41A_3 120.4(3) . . ?
C35A_3 C34A_3 C33A_3 120.5(3) . . ?
C35A_3 C34A_3 H34A_3 119.8 . . ?
C33A_3 C34A_3 H34A_3 119.8 . . ?
C34A_3 C35A_3 C36A_3 119.9(3) . . ?
C34A_3 C35A_3 H35A_3 120.1 . . ?
C36A_3 C35A_3 H35A_3 120.1 . . ?
C31A_3 C36A_3 C35A_3 121.0(3) . . ?
C31A_3 C36A_3 C37A_3 117.5(3) . . ?
C35A_3 C36A_3 C37A_3 121.6(3) . . ?
C38A_3 C37A_3 C36A_3 122.4(3) . . ?
C38A_3 C37A_3 H37A_3 118.8 . . ?
C36A_3 C37A_3 H37A_3 118.8 . . ?
C37A_3 C38A_3 C39A_3 118.4(3) . . ?
C37A_3 C38A_3 H38A_3 120.8 . . ?
C39A_3 C38A_3 H38A_3 120.8 . . ?
C40A_3 C39A_3 C38A_3 121.7(3) . . ?
C40A_3 C39A_3 H39A_3 119.2 . . ?
C38A_3 C39A_3 H39A_3 119.2 . . ?
C39A_3 C40A_3 C31A_3 118.6(3) . . ?
C39A_3 C40A_3 H40A_3 120.7 . . ?
C31A_3 C40A_3 H40A_3 120.7 . . ?
O42A_3 C41A_3 O41A_3 123.5(3) . . ?
O42A_3 C41A_3 C33A_3 119.5(4) . . ?
O41A_3 C41A_3 C33A_3 116.8(3) . . ?
C36B_3 C31B_3 C40B_3 121.6(5) . . ?
C36B_3 C31B_3 C32B_3 118.5(4) . . ?
C40B_3 C31B_3 C32B_3 119.9(5) . . ?
O32B_3 C32B_3 C33B_3 122.6(4) . . ?
O32B_3 C32B_3 C31B_3 116.6(4) . . ?
C33B_3 C32B_3 C31B_3 120.7(4) . . ?
C32B_3 O32B_3 H32B_3 102(3) . . ?
C32B_3 C33B_3 C34B_3 119.2(4) . . ?
C32B_3 C33B_3 C41B_3 120.7(5) . . ?
C34B_3 C33B_3 C41B_3 120.0(5) . . ?
C35B_3 C34B_3 C33B_3 120.5(5) . . ?
C35B_3 C34B_3 H32A_3 118(4) . . ?
C33B_3 C34B_3 H32A_3 121(4) . . ?
C35B_3 C34B_3 H34B_3 119.7 . . ?
C33B_3 C34B_3 H34B_3 119.7 . . ?
C34B_3 C35B_3 C36B_3 120.3(4) . . ?
C34B_3 C35B_3 H35B_3 119.8 . . ?
C36B_3 C35B_3 H35B_3 119.8 . . ?
C31B_3 C36B_3 C35B_3 120.6(4) . . ?
C31B_3 C36B_3 C37B_3 118.1(5) . . ?
C35B_3 C36B_3 C37B_3 121.3(5) . . ?
C38B_3 C37B_3 C36B_3 120.6(6) . . ?
C38B_3 C37B_3 H37B_3 119.7 . . ?
C36B_3 C37B_3 H37B_3 119.7 . . ?
C37B_3 C38B_3 C39B_3 120.0(5) . . ?
C37B_3 C38B_3 H38B_3 120.0 . . ?
C39B_3 C38B_3 H38B_3 120.0 . . ?
C40B_3 C39B_3 C38B_3 121.4(6) . . ?
C40B_3 C39B_3 H39B_3 119.3 . . ?
C38B_3 C39B_3 H39B_3 119.3 . . ?
C39B_3 C40B_3 C31B_3 118.3(5) . . ?
C39B_3 C40B_3 H40B_3 120.9 . . ?
C31B_3 C40B_3 H40B_3 120.9 . . ?
O42B_3 C41B_3 O41B_3 124.4(4) . . ?
O42B_3 C41B_3 C33B_3 116.7(6) . . ?
O41B_3 C41B_3 C33B_3 118.5(5) . . ?

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
C16_1 N11_1 C12_1 N12_1 -178.23(13) . . . . ?
O11_1 N11_1 C12_1 N12_1 1.30(19) . . . . ?
C16_1 N11_1 C12_1 N13_1 2.2(2) . . . . ?
O11_1 N11_1 C12_1 N13_1 -178.26(12) . . . . ?
N12_1 C12_1 N13_1 C14_1 -178.91(14) . . . . ?
N11_1 C12_1 N13_1 C14_1 0.6(2) . . . . ?
C12_1 N13_1 C14_1 N21_1 175.96(12) . . . . ?
C12_1 N13_1 C14_1 C15_1 -3.1(2) . . . . ?
N21_1 C14_1 C15_1 C16_1 -176.34(13) . . . . ?
N13_1 C14_1 C15_1 C16_1 2.7(2) . . . . ?
C14_1 C15_1 C16_1 N16_1 178.42(15) . . . . ?
C14_1 C15_1 C16_1 N11_1 0.1(2) . . . . ?
C12_1 N11_1 C16_1 N16_1 178.98(14) . . . . ?
O11_1 N11_1 C16_1 N16_1 -0.5(2) . . . . ?
C12_1 N11_1 C16_1 C15_1 -2.6(2) . . . . ?
O11_1 N11_1 C16_1 C15_1 177.88(13) . . . . ?
C15_1 C14_1 N21_1 C26_1 -6.1(2) . . . . ?
N13_1 C14_1 N21_1 C26_1 174.77(13) . . . . ?
C15_1 C14_1 N21_1 C22_1 -177.02(13) . . . . ?
N13_1 C14_1 N21_1 C22_1 3.9(2) . . . . ?
C14_1 N21_1 C22_1 C23_1 -133.17(14) . . . . ?
C26_1 N21_1 C22_1 C23_1 55.22(16) . . . . ?
N21_1 C22_1 C23_1 C24_1 -53.76(16) . . . . ?
C22_1 C23_1 C24_1 C25_1 54.41(17) . . . . ?
C23_1 C24_1 C25_1 C26_1 -55.11(18) . . . . ?
C14_1 N21_1 C26_1 C25_1 131.85(15) . . . . ?
C22_1 N21_1 C26_1 C25_1 -56.54(18) . . . . ?
C24_1 C25_1 C26_1 N21_1 55.76(18) . . . . ?
C16_2 N11_2 C12_2 N12_2 -179.08(15) . . . . ?
O11_2 N11_2 C12_2 N12_2 -3.7(2) . . . . ?
C16_2 N11_2 C12_2 N13_2 2.3(2) . . . . ?
O11_2 N11_2 C12_2 N13_2 177.69(14) . . . . ?
N12_2 C12_2 N13_2 C14_2 -178.40(17) . . . . ?
N11_2 C12_2 N13_2 C14_2 0.1(2) . . . . ?
C12_2 N13_2 C14_2 N21_2 -179.45(14) . . . . ?
C12_2 N13_2 C14_2 C15_2 -1.4(2) . . . . ?
N13_2 C14_2 C15_2 C16_2 0.3(2) . . . . ?
N21_2 C14_2 C15_2 C16_2 178.29(14) . . . . ?
C12_2 N11_2 C16_2 N16_2 178.43(14) . . . . ?
O11_2 N11_2 C16_2 N16_2 3.1(2) . . . . ?
C12_2 N11_2 C16_2 C15_2 -3.3(2) . . . . ?
O11_2 N11_2 C16_2 C15_2 -178.71(13) . . . . ?
C14_2 C15_2 C16_2 N16_2 -179.94(15) . . . . ?
C14_2 C15_2 C16_2 N11_2 2.0(2) . . . . ?
N13_2 C14_2 N21_2 C26_2 -161.09(14) . . . . ?
C15_2 C14_2 N21_2 C26_2 20.8(2) . . . . ?
N13_2 C14_2 N21_2 C22_2 -10.7(2) . . . . ?
C15_2 C14_2 N21_2 C22_2 171.22(14) . . . . ?
C14_2 N21_2 C22_2 C23_2 158.68(14) . . . . ?
C26_2 N21_2 C22_2 C23_2 -49.51(19) . . . . ?
N21_2 C22_2 C23_2 C24_2 52.8(2) . . . . ?
C22_2 C23_2 C24_2 C25_2 -56.5(2) . . . . ?
C23_2 C24_2 C25_2 C26_2 56.3(2) . . . . ?
C14_2 N21_2 C26_2 C25_2 -158.79(15) . . . . ?
C22_2 N21_2 C26_2 C25_2 50.0(2) . . . . ?
C24_2 C25_2 C26_2 N21_2 -53.1(2) . . . . ?
C36A_3 C31A_3 C32A_3 O32A_3 179.2(3) . . . . ?
C40A_3 C31A_3 C32A_3 O32A_3 0.7(5) . . . . ?
C36A_3 C31A_3 C32A_3 C33A_3 -0.4(5) . . . . ?
C40A_3 C31A_3 C32A_3 C33A_3 -179.0(4) . . . . ?
O32A_3 C32A_3 C33A_3 C34A_3 -179.8(3) . . . . ?
C31A_3 C32A_3 C33A_3 C34A_3 -0.2(6) . . . . ?
O32A_3 C32A_3 C33A_3 C41A_3 -1.0(6) . . . . ?
C31A_3 C32A_3 C33A_3 C41A_3 178.6(4) . . . . ?
C32A_3 C33A_3 C34A_3 C35A_3 0.0(6) . . . . ?
C41A_3 C33A_3 C34A_3 C35A_3 -178.8(4) . . . . ?
C33A_3 C34A_3 C35A_3 C36A_3 0.8(5) . . . . ?
C40A_3 C31A_3 C36A_3 C35A_3 179.7(3) . . . . ?
C32A_3 C31A_3 C36A_3 C35A_3 1.2(5) . . . . ?
C40A_3 C31A_3 C36A_3 C37A_3 0.9(6) . . . . ?
C32A_3 C31A_3 C36A_3 C37A_3 -177.6(4) . . . . ?
C34A_3 C35A_3 C36A_3 C31A_3 -1.4(4) . . . . ?
C34A_3 C35A_3 C36A_3 C37A_3 177.4(4) . . . . ?
C31A_3 C36A_3 C37A_3 C38A_3 0.7(8) . . . . ?
C35A_3 C36A_3 C37A_3 C38A_3 -178.1(5) . . . . ?
C36A_3 C37A_3 C38A_3 C39A_3 -1.9(9) . . . . ?
C37A_3 C38A_3 C39A_3 C40A_3 1.6(8) . . . . ?
C38A_3 C39A_3 C40A_3 C31A_3 -0.1(7) . . . . ?
C36A_3 C31A_3 C40A_3 C39A_3 -1.2(6) . . . . ?
C32A_3 C31A_3 C40A_3 C39A_3 177.3(4) . . . . ?
C32A_3 C33A_3 C41A_3 O42A_3 -178.8(4) . . . . ?
C34A_3 C33A_3 C41A_3 O42A_3 0.0(7) . . . . ?
C32A_3 C33A_3 C41A_3 O41A_3 -2.5(7) . . . . ?
C34A_3 C33A_3 C41A_3 O41A_3 176.3(4) . . . . ?
C36B_3 C31B_3 C32B_3 O32B_3 -179.0(7) . . . . ?
C40B_3 C31B_3 C32B_3 O32B_3 -1.2(8) . . . . ?
C36B_3 C31B_3 C32B_3 C33B_3 -2.7(10) . . . . ?
C40B_3 C31B_3 C32B_3 C33B_3 175.2(8) . . . . ?
O32B_3 C32B_3 C33B_3 C34B_3 179.1(7) . . . . ?
C31B_3 C32B_3 C33B_3 C34B_3 3.0(13) . . . . ?
O32B_3 C32B_3 C33B_3 C41B_3 4.2(15) . . . . ?
C31B_3 C32B_3 C33B_3 C41B_3 -172.0(9) . . . . ?
C32B_3 C33B_3 C34B_3 C35B_3 0.0(14) . . . . ?
C41B_3 C33B_3 C34B_3 C35B_3 175.1(9) . . . . ?
C33B_3 C34B_3 C35B_3 C36B_3 -3.5(12) . . . . ?
C40B_3 C31B_3 C36B_3 C35B_3 -178.6(7) . . . . ?
C32B_3 C31B_3 C36B_3 C35B_3 -0.8(12) . . . . ?
C40B_3 C31B_3 C36B_3 C37B_3 0.0(13) . . . . ?
C32B_3 C31B_3 C36B_3 C37B_3 177.8(7) . . . . ?
C34B_3 C35B_3 C36B_3 C31B_3 3.8(13) . . . . ?
C34B_3 C35B_3 C36B_3 C37B_3 -174.7(8) . . . . ?
C31B_3 C36B_3 C37B_3 C38B_3 1.1(15) . . . . ?
C35B_3 C36B_3 C37B_3 C38B_3 179.7(11) . . . . ?
C36B_3 C37B_3 C38B_3 C39B_3 -1(2) . . . . ?
C37B_3 C38B_3 C39B_3 C40B_3 0(2) . . . . ?
C38B_3 C39B_3 C40B_3 C31B_3 0.7(19) . . . . ?
C36B_3 C31B_3 C40B_3 C39B_3 -0.9(13) . . . . ?
C32B_3 C31B_3 C40B_3 C39B_3 -178.7(9) . . . . ?
C32B_3 C33B_3 C41B_3 O42B_3 177.7(10) . . . . ?
C34B_3 C33B_3 C41B_3 O42B_3 2.7(17) . . . . ?
C32B_3 C33B_3 C41B_3 O41B_3 -8.7(17) . . . . ?
C34B_3 C33B_3 C41B_3 O41B_3 176.4(10) . . . . ?

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
O1S H1A O42A_3 1.04(5) 2.01(5) 3.021(4) 163(4) .
O1S H1A O42B_3 1.04(5) 1.55(5) 2.440(5) 140(4) .
O11_1 H11_1 O11_2 1.198(18) 1.219(19) 2.4166(18) 177.9(17) .
N12_1 H12A_1 O42A_3 0.95(2) 2.00(2) 2.944(2) 171.2(16) 2_566
N12_1 H12A_1 O41B_3 0.95(2) 2.03(2) 2.963(4) 166.2(16) 2_566
N16_1 H16A_1 O42A_3 0.88(2) 2.12(2) 2.965(3) 161.0(19) 2_666
N16_1 H16A_1 O41B_3 0.88(2) 2.02(2) 2.900(4) 176(2) 2_666
N12_2 H12A_2 O41A_3 0.87(3) 1.92(3) 2.783(3) 168(2) 1_655
N12_2 H12A_2 O42B_3 0.87(3) 2.17(3) 2.907(5) 142(2) 1_655
N12_2 H12B_2 O1S 0.92(3) 2.09(3) 2.840(3) 137(2) 2_666
N16_2 H16B_2 O41A_3 0.92(2) 2.01(3) 2.924(3) 173(2) .
N16_2 H16B_2 O42B_3 0.92(2) 1.87(3) 2.708(4) 150(2) .
O32A_3 H32A_3 O41A_3 0.88(4) 1.64(4) 2.490(4) 161(4) .
O32B_3 H32B_3 O41B_3 1.03(6) 1.59(6) 2.556(6) 155(5) .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.042

# Attachment '_9__cif1.cif'

data_ns0804m
_database_code_depnum_ccdc_archive 'CCDC 733883'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3189-80-04 minoxidil : benzoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C9 H15 N5 O) (C7 H6 O2)
;
_chemical_formula_sum            'C16 H21 N5 O3'
_chemical_formula_weight         331.38

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0011(7)
_cell_length_b                   12.1067(7)
_cell_length_c                   12.5719(8)
_cell_angle_alpha                66.822(2)
_cell_angle_beta                 88.582(2)
_cell_angle_gamma                79.951(2)
_cell_volume                     1651.48(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1899
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      29.88

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9766
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_process_details   TWINABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14017
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.54
_diffrn_reflns_theta_max         30.49
_reflns_number_total             14017
_reflns_number_gt                8162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0750P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         14017
_refine_ls_number_parameters     491
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1299
_refine_ls_R_factor_gt           0.0670
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N11_1 N 0.46158(11) 0.54927(14) 0.18915(13) 0.0223(3) Uani 1 1 d . A .
O11_1 O 0.50657(9) 0.59360(12) 0.08186(11) 0.0257(3) Uani 1 1 d . . .
C12_1 C 0.43210(13) 0.43635(17) 0.23003(17) 0.0250(4) Uani 1 1 d . . .
N12_1 N 0.44503(15) 0.37780(18) 0.15938(18) 0.0359(4) Uani 1 1 d . A .
H12A_1 H 0.4700(18) 0.413(2) 0.094(2) 0.043 Uiso 1 1 d . . .
H12B_1 H 0.4367(18) 0.302(3) 0.183(2) 0.043 Uiso 1 1 d . . .
N13_1 N 0.39073(12) 0.39039(16) 0.33813(15) 0.0256(4) Uani 0.432(16) 1 d P A .
C13_1 C 0.39073(12) 0.39039(16) 0.33813(15) 0.0256(4) Uani 0.568(16) 1 d P A 2
H13_1 H 0.3708 0.3115 0.3681 0.031 Uiso 0.568(16) 1 calc PR A 2
C14_1 C 0.37849(13) 0.46064(17) 0.40259(16) 0.0242(4) Uani 1 1 d . . .
C15_1 C 0.40206(13) 0.57712(17) 0.35874(15) 0.0274(4) Uani 0.432(16) 1 d P A 1
H15_1 H 0.3894 0.6263 0.4025 0.033 Uiso 0.432(16) 1 calc PR A 1
N15_1 N 0.40206(13) 0.57712(17) 0.35874(15) 0.0274(4) Uani 0.568(16) 1 d P A 2
C16_1 C 0.44358(13) 0.61990(18) 0.25223(16) 0.0252(4) Uani 1 1 d . . .
N16_1 N 0.47210(15) 0.72997(18) 0.20355(18) 0.0359(4) Uani 1 1 d . A .
H16A_1 H 0.4747(18) 0.764(2) 0.125(2) 0.043 Uiso 1 1 d . . .
H16B_1 H 0.4612(19) 0.773(2) 0.239(2) 0.043 Uiso 1 1 d . . .
N21_1 N 0.34326(13) 0.41540(15) 0.51258(14) 0.0290(4) Uani 1 1 d . A .
C22_1 C 0.29237(15) 0.30522(18) 0.55792(18) 0.0313(4) Uani 1 1 d . . .
H22A_1 H 0.3180 0.2570 0.6401 0.038 Uiso 1 1 calc R A .
H22B_1 H 0.3175 0.2541 0.5137 0.038 Uiso 1 1 calc R . .
C23_1 C 0.16371(15) 0.33908(19) 0.54836(18) 0.0322(4) Uani 1 1 d . A .
H23A_1 H 0.1305 0.2642 0.5844 0.039 Uiso 1 1 calc R . .
H23B_1 H 0.1376 0.3790 0.4657 0.039 Uiso 1 1 calc R . .
C24_1 C 0.12324(15) 0.42559(19) 0.60869(18) 0.0317(4) Uani 1 1 d . . .
H24A_1 H 0.0403 0.4533 0.5948 0.038 Uiso 1 1 calc R A .
H24B_1 H 0.1394 0.3815 0.6932 0.038 Uiso 1 1 calc R . .
C25_1 C 0.18209(16) 0.53623(19) 0.56383(18) 0.0335(4) Uani 1 1 d . A .
H25A_1 H 0.1584 0.5863 0.4815 0.040 Uiso 1 1 calc R . .
H25B_1 H 0.1598 0.5873 0.6086 0.040 Uiso 1 1 calc R . .
C26_1 C 0.30987(16) 0.4942(2) 0.57563(19) 0.0356(5) Uani 1 1 d . . .
H26A_1 H 0.3478 0.5661 0.5443 0.043 Uiso 1 1 calc R A .
H26B_1 H 0.3340 0.4488 0.6585 0.043 Uiso 1 1 calc R . .
C31_1 C 0.90452(13) 0.51782(18) 0.13126(16) 0.0252(4) Uani 1 1 d D . .
C37_1 C 0.78232(14) 0.50522(18) 0.13445(16) 0.0258(4) Uani 1 1 d D . .
O31_1 O 0.71011(10) 0.60781(12) 0.09288(12) 0.0293(3) Uani 1 1 d D . .
H31_1 H 0.6197(17) 0.597(2) 0.0923(19) 0.035 Uiso 1 1 d . . .
O32_1 O 0.75391(11) 0.40460(13) 0.17607(13) 0.0360(3) Uani 1 1 d D . .
C32_1 C 0.98571(16) 0.4192(2) 0.19801(19) 0.0378(5) Uani 1 1 d D . .
H32_1 H 0.9644 0.3434 0.2444 0.045 Uiso 1 1 calc R . .
C33_1 C 1.10032(16) 0.4327(2) 0.1963(2) 0.0445(6) Uani 1 1 d D . .
H33_1 H 1.1564 0.3666 0.2433 0.053 Uiso 1 1 calc R . .
C34_1 C 1.13033(16) 0.5418(2) 0.1266(2) 0.0426(6) Uani 1 1 d D . .
H34_1 H 1.2077 0.5499 0.1251 0.051 Uiso 1 1 calc R . .
C35_1 C 1.05065(16) 0.6398(2) 0.0586(2) 0.0401(5) Uani 1 1 d D . .
H35_1 H 1.0728 0.7147 0.0106 0.048 Uiso 1 1 calc R . .
C36_1 C 0.93757(14) 0.62780(19) 0.06128(18) 0.0301(4) Uani 1 1 d D . .
H36_1 H 0.8821 0.6951 0.0150 0.036 Uiso 1 1 calc R . .
N11_2 N 0.32799(11) -0.05559(14) 0.91597(14) 0.0237(3) Uani 1 1 d . B .
O11_2 O 0.43962(9) -0.09761(13) 0.95474(12) 0.0302(3) Uani 1 1 d . . .
C12_2 C 0.26832(13) -0.13009(17) 0.89262(15) 0.0233(4) Uani 1 1 d . . .
N12_2 N 0.31959(14) -0.24548(16) 0.92022(16) 0.0305(4) Uani 1 1 d . B .
H12A_2 H 0.3883(19) -0.275(2) 0.955(2) 0.037 Uiso 1 1 d . . .
H12B_2 H 0.2883(18) -0.288(2) 0.897(2) 0.037 Uiso 1 1 d . . .
N13_2 N 0.16323(11) -0.08977(15) 0.84464(13) 0.0231(4) Uani 0.765(16) 1 d P B .
C13_2 C 0.16323(11) -0.08977(15) 0.84464(13) 0.0231(4) Uani 0.235(16) 1 d P B 2
H13_2 H 0.1228 -0.1427 0.8286 0.028 Uiso 0.235(16) 1 calc PR B 2
C14_2 C 0.11536(13) 0.02870(17) 0.81924(15) 0.0242(4) Uani 1 1 d . . .
C15_2 C 0.16901(13) 0.10373(17) 0.85200(16) 0.0273(4) Uani 0.765(16) 1 d P B 1
H15_2 H 0.1316 0.1836 0.8410 0.033 Uiso 0.765(16) 1 calc PR B 1
N15_2 N 0.16901(13) 0.10373(17) 0.85200(16) 0.0273(4) Uani 0.235(16) 1 d P B 2
C16_2 C 0.27741(14) 0.06031(18) 0.90080(16) 0.0254(4) Uani 1 1 d . . .
N16_2 N 0.33849(14) 0.12296(18) 0.93641(17) 0.0331(4) Uani 1 1 d . B .
H16A_2 H 0.4064(19) 0.089(2) 0.961(2) 0.040 Uiso 1 1 d . . .
H16B_2 H 0.3089(18) 0.202(2) 0.928(2) 0.040 Uiso 1 1 d . . .
N21_2 N 0.01393(12) 0.07057(15) 0.75893(15) 0.0295(4) Uani 1 1 d . B .
C22_2 C -0.04930(16) -0.0123(2) 0.7367(2) 0.0394(5) Uani 1 1 d . . .
H22A_2 H 0.0027 -0.0890 0.7461 0.047 Uiso 1 1 calc R B .
H22B_2 H -0.0815 0.0262 0.6560 0.047 Uiso 1 1 calc R . .
C23_2 C -0.14428(17) -0.0409(2) 0.8200(2) 0.0386(5) Uani 1 1 d . B .
H23A_2 H -0.1119 -0.0850 0.9005 0.046 Uiso 1 1 calc R . .
H23B_2 H -0.1884 -0.0939 0.8022 0.046 Uiso 1 1 calc R . .
C24_2 C -0.22181(15) 0.0776(2) 0.80889(19) 0.0352(5) Uani 1 1 d . . .
H24A_2 H -0.2598 0.1175 0.7307 0.042 Uiso 1 1 calc R B .
H24B_2 H -0.2810 0.0592 0.8664 0.042 Uiso 1 1 calc R . .
C25_2 C -0.15441(15) 0.1638(2) 0.82854(19) 0.0330(4) Uani 1 1 d . B .
H25A_2 H -0.1233 0.1279 0.9096 0.040 Uiso 1 1 calc R . .
H25B_2 H -0.2049 0.2424 0.8157 0.040 Uiso 1 1 calc R . .
C26_2 C -0.05776(15) 0.18647(18) 0.74594(18) 0.0314(4) Uani 1 1 d . . .
H26A_2 H -0.0892 0.2300 0.6651 0.038 Uiso 1 1 calc R B .
H26B_2 H -0.0117 0.2386 0.7627 0.038 Uiso 1 1 calc R . .
C31A_2 C 0.6078(4) 0.0200(9) 0.6085(7) 0.0258(9) Uani 0.523(2) 1 d PD C 1
C37A_2 C 0.5396(5) 0.0037(5) 0.7113(5) 0.0274(7) Uani 0.523(2) 1 d PD C 1
O31A_2 O 0.54996(18) -0.1080(2) 0.7920(2) 0.0236(6) Uani 0.523(2) 1 d PD C 1
H31A_2 H 0.5171 -0.1058 0.8511 0.028 Uiso 0.523(2) 1 calc PR C 1
O32A_2 O 0.4777(2) 0.0923(3) 0.7208(2) 0.0263(6) Uani 0.523(2) 1 d PD C 1
C32A_2 C 0.598(3) 0.1382(15) 0.520(2) 0.040(3) Uani 0.523(2) 1 d PD C 1
H32A_2 H 0.5393 0.2002 0.5236 0.048 Uiso 0.523(2) 1 calc PR C 1
C33A_2 C 0.669(2) 0.1693(15) 0.4279(19) 0.0553(17) Uani 0.523(2) 1 d PD C 1
H33A_2 H 0.6668 0.2511 0.3741 0.066 Uiso 0.523(2) 1 calc PR C 1
C34A_2 C 0.7460(4) 0.0706(6) 0.4200(5) 0.0465(6) Uani 0.523(2) 1 d PD C 1
H34A_2 H 0.7904 0.0846 0.3539 0.056 Uiso 0.523(2) 1 calc PR C 1
C35A_2 C 0.7586(4) -0.0476(5) 0.5069(5) 0.0465(6) Uani 0.523(2) 1 d PD C 1
H35A_2 H 0.8139 -0.1112 0.5009 0.056 Uiso 0.523(2) 1 calc PR C 1
C36A_2 C 0.6899(4) -0.0724(5) 0.6027(5) 0.0465(6) Uani 0.523(2) 1 d PD C 1
H36A_2 H 0.6999 -0.1519 0.6628 0.056 Uiso 0.523(2) 1 calc PR C 1
C31B_2 C 0.6405(5) 0.0152(10) 0.5991(8) 0.0258(9) Uani 0.477(2) 1 d PD C 2
C37B_2 C 0.5919(3) -0.0495(4) 0.7107(4) 0.0274(7) Uani 0.477(2) 1 d PD C 2
O31B_2 O 0.5203(3) 0.0209(4) 0.7466(4) 0.0371(11) Uani 0.477(2) 1 d PD C 2
H31B_2 H 0.4974 -0.0211 0.8111 0.045 Uiso 0.477(2) 1 calc PR C 2
O32B_2 O 0.6224(3) -0.1599(3) 0.7663(3) 0.0458(9) Uani 0.477(2) 1 d PD C 2
C32B_2 C 0.7256(4) -0.0517(5) 0.5580(5) 0.0465(6) Uani 0.477(2) 1 d PD C 2
H32B_2 H 0.7494 -0.1368 0.6016 0.056 Uiso 0.477(2) 1 calc PR C 2
C33B_2 C 0.7756(5) 0.0065(7) 0.4527(6) 0.0465(6) Uani 0.477(2) 1 d PD C 2
H33B_2 H 0.8322 -0.0380 0.4235 0.056 Uiso 0.477(2) 1 calc PR C 2
C34B_2 C 0.7388(5) 0.1328(6) 0.3924(5) 0.0465(6) Uani 0.477(2) 1 d PD C 2
H34B_2 H 0.7776 0.1758 0.3264 0.056 Uiso 0.477(2) 1 calc PR C 2
C35B_2 C 0.649(2) 0.1947(16) 0.426(2) 0.0553(17) Uani 0.477(2) 1 d PD C 2
H35B_2 H 0.6182 0.2765 0.3770 0.066 Uiso 0.477(2) 1 calc PR C 2
C36B_2 C 0.603(3) 0.1389(17) 0.531(2) 0.040(3) Uani 0.477(2) 1 d PD C 2
H36B_2 H 0.5456 0.1850 0.5577 0.048 Uiso 0.477(2) 1 calc PR C 2


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N11_1 C12_1 1.366(2) . ?
N11_1 C16_1 1.367(2) . ?
N11_1 O11_1 1.3763(18) . ?
O11_1 H31_1 1.38(2) . ?
C12_1 N12_1 1.329(3) . ?
C12_1 N13_1 1.368(2) . ?
N12_1 H12A_1 0.84(3) . ?
N12_1 H12B_1 0.86(3) . ?
N13_1 C14_1 1.377(3) . ?
C14_1 N21_1 1.359(2) . ?
C14_1 C15_1 1.376(3) . ?
C15_1 C16_1 1.349(2) . ?
C15_1 H15_1 0.9500 . ?
C16_1 N16_1 1.332(3) . ?
N16_1 H16A_1 0.91(3) . ?
N16_1 H16B_1 0.80(3) . ?
N21_1 C26_1 1.465(3) . ?
N21_1 C22_1 1.465(2) . ?
C22_1 C23_1 1.522(3) . ?
C22_1 H22A_1 0.9900 . ?
C22_1 H22B_1 0.9900 . ?
C23_1 C24_1 1.529(3) . ?
C23_1 H23A_1 0.9900 . ?
C23_1 H23B_1 0.9900 . ?
C24_1 C25_1 1.525(3) . ?
C24_1 H24A_1 0.9900 . ?
C24_1 H24B_1 0.9900 . ?
C25_1 C26_1 1.521(3) . ?
C25_1 H25A_1 0.9900 . ?
C25_1 H25B_1 0.9900 . ?
C26_1 H26A_1 0.9900 . ?
C26_1 H26B_1 0.9900 . ?
C31_1 C32_1 1.387(3) . ?
C31_1 C36_1 1.396(3) . ?
C31_1 C37_1 1.499(2) . ?
C37_1 O32_1 1.228(2) . ?
C37_1 O31_1 1.305(2) . ?
O31_1 H31_1 1.12(2) . ?
C32_1 C33_1 1.412(3) . ?
C32_1 H32_1 0.9500 . ?
C33_1 C34_1 1.371(3) . ?
C33_1 H33_1 0.9500 . ?
C34_1 C35_1 1.378(3) . ?
C34_1 H34_1 0.9500 . ?
C35_1 C36_1 1.388(2) . ?
C35_1 H35_1 0.9500 . ?
C36_1 H36_1 0.9500 . ?
N11_2 C12_2 1.363(2) . ?
N11_2 C16_2 1.368(2) . ?
N11_2 O11_2 1.3749(17) . ?
C12_2 N12_2 1.334(2) . ?
C12_2 N13_2 1.336(2) . ?
N12_2 H12A_2 0.89(2) . ?
N12_2 H12B_2 0.83(2) . ?
N13_2 C14_2 1.360(2) . ?
C14_2 N21_2 1.357(2) . ?
C14_2 C15_2 1.386(3) . ?
C15_2 C16_2 1.376(2) . ?
C15_2 H15_2 0.9500 . ?
C16_2 N16_2 1.338(3) . ?
N16_2 H16A_2 0.85(2) . ?
N16_2 H16B_2 0.92(3) . ?
N21_2 C26_2 1.463(2) . ?
N21_2 C22_2 1.469(3) . ?
C22_2 C23_2 1.520(3) . ?
C22_2 H22A_2 0.9900 . ?
C22_2 H22B_2 0.9900 . ?
C23_2 C24_2 1.525(3) . ?
C23_2 H23A_2 0.9900 . ?
C23_2 H23B_2 0.9900 . ?
C24_2 C25_2 1.521(3) . ?
C24_2 H24A_2 0.9900 . ?
C24_2 H24B_2 0.9900 . ?
C25_2 C26_2 1.525(3) . ?
C25_2 H25A_2 0.9900 . ?
C25_2 H25B_2 0.9900 . ?
C26_2 H26A_2 0.9900 . ?
C26_2 H26B_2 0.9900 . ?
C31A_2 C36A_2 1.381(8) . ?
C31A_2 C32A_2 1.412(11) . ?
C31A_2 C37A_2 1.477(7) . ?
C37A_2 O32A_2 1.238(6) . ?
C37A_2 O31A_2 1.319(6) . ?
O31A_2 H31A_2 0.8400 . ?
C32A_2 C33A_2 1.392(12) . ?
C32A_2 H32A_2 0.9500 . ?
C33A_2 C34A_2 1.409(12) . ?
C33A_2 H33A_2 0.9500 . ?
C34A_2 C35A_2 1.402(7) . ?
C34A_2 H34A_2 0.9500 . ?
C35A_2 C36A_2 1.405(6) . ?
C35A_2 H35A_2 0.9500 . ?
C36A_2 H36A_2 0.9500 . ?
C31B_2 C36B_2 1.396(13) . ?
C31B_2 C32B_2 1.408(8) . ?
C31B_2 C37B_2 1.475(8) . ?
C37B_2 O32B_2 1.231(5) . ?
C37B_2 O31B_2 1.303(5) . ?
O31B_2 H31B_2 0.8400 . ?
C32B_2 C33B_2 1.408(8) . ?
C32B_2 H32B_2 0.9500 . ?
C33B_2 C34B_2 1.405(8) . ?
C33B_2 H33B_2 0.9500 . ?
C34B_2 C35B_2 1.357(12) . ?
C34B_2 H34B_2 0.9500 . ?
C35B_2 C36B_2 1.379(13) . ?
C35B_2 H35B_2 0.9500 . ?
C36B_2 H36B_2 0.9500 . ?

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
C12_1 N11_1 C16_1 120.59(15) . . ?
C12_1 N11_1 O11_1 119.55(15) . . ?
C16_1 N11_1 O11_1 119.84(15) . . ?
N11_1 O11_1 H31_1 110.8(9) . . ?
N12_1 C12_1 N11_1 116.46(17) . . ?
N12_1 C12_1 N13_1 123.83(19) . . ?
N11_1 C12_1 N13_1 119.70(17) . . ?
C12_1 N12_1 H12A_1 117.7(18) . . ?
C12_1 N12_1 H12B_1 120.8(17) . . ?
H12A_1 N12_1 H12B_1 121(2) . . ?
C12_1 N13_1 C14_1 118.70(17) . . ?
N21_1 C14_1 C15_1 118.21(17) . . ?
N21_1 C14_1 N13_1 120.27(17) . . ?
C15_1 C14_1 N13_1 121.52(16) . . ?
C16_1 C15_1 C14_1 118.51(17) . . ?
C16_1 C15_1 H15_1 120.7 . . ?
C14_1 C15_1 H15_1 120.7 . . ?
N16_1 C16_1 C15_1 123.08(19) . . ?
N16_1 C16_1 N11_1 116.10(17) . . ?
C15_1 C16_1 N11_1 120.79(18) . . ?
C16_1 N16_1 H16A_1 118.1(16) . . ?
C16_1 N16_1 H16B_1 117.3(18) . . ?
H16A_1 N16_1 H16B_1 120(2) . . ?
C14_1 N21_1 C26_1 121.41(17) . . ?
C14_1 N21_1 C22_1 122.11(16) . . ?
C26_1 N21_1 C22_1 112.02(15) . . ?
N21_1 C22_1 C23_1 110.43(16) . . ?
N21_1 C22_1 H22A_1 109.6 . . ?
C23_1 C22_1 H22A_1 109.6 . . ?
N21_1 C22_1 H22B_1 109.6 . . ?
C23_1 C22_1 H22B_1 109.6 . . ?
H22A_1 C22_1 H22B_1 108.1 . . ?
C22_1 C23_1 C24_1 110.55(16) . . ?
C22_1 C23_1 H23A_1 109.5 . . ?
C24_1 C23_1 H23A_1 109.5 . . ?
C22_1 C23_1 H23B_1 109.5 . . ?
C24_1 C23_1 H23B_1 109.5 . . ?
H23A_1 C23_1 H23B_1 108.1 . . ?
C25_1 C24_1 C23_1 110.98(16) . . ?
C25_1 C24_1 H24A_1 109.4 . . ?
C23_1 C24_1 H24A_1 109.4 . . ?
C25_1 C24_1 H24B_1 109.4 . . ?
C23_1 C24_1 H24B_1 109.4 . . ?
H24A_1 C24_1 H24B_1 108.0 . . ?
C26_1 C25_1 C24_1 109.81(17) . . ?
C26_1 C25_1 H25A_1 109.7 . . ?
C24_1 C25_1 H25A_1 109.7 . . ?
C26_1 C25_1 H25B_1 109.7 . . ?
C24_1 C25_1 H25B_1 109.7 . . ?
H25A_1 C25_1 H25B_1 108.2 . . ?
N21_1 C26_1 C25_1 110.10(16) . . ?
N21_1 C26_1 H26A_1 109.6 . . ?
C25_1 C26_1 H26A_1 109.6 . . ?
N21_1 C26_1 H26B_1 109.6 . . ?
C25_1 C26_1 H26B_1 109.6 . . ?
H26A_1 C26_1 H26B_1 108.2 . . ?
C32_1 C31_1 C36_1 119.61(17) . . ?
C32_1 C31_1 C37_1 119.78(18) . . ?
C36_1 C31_1 C37_1 120.61(16) . . ?
O32_1 C37_1 O31_1 123.36(16) . . ?
O32_1 C37_1 C31_1 121.35(16) . . ?
O31_1 C37_1 C31_1 115.27(16) . . ?
C37_1 O31_1 H31_1 114.6(11) . . ?
C31_1 C32_1 C33_1 119.4(2) . . ?
C31_1 C32_1 H32_1 120.3 . . ?
C33_1 C32_1 H32_1 120.3 . . ?
C34_1 C33_1 C32_1 119.7(2) . . ?
C34_1 C33_1 H33_1 120.1 . . ?
C32_1 C33_1 H33_1 120.1 . . ?
C33_1 C34_1 C35_1 121.43(19) . . ?
C33_1 C34_1 H34_1 119.3 . . ?
C35_1 C34_1 H34_1 119.3 . . ?
C34_1 C35_1 C36_1 119.2(2) . . ?
C34_1 C35_1 H35_1 120.4 . . ?
C36_1 C35_1 H35_1 120.4 . . ?
C35_1 C36_1 C31_1 120.69(19) . . ?
C35_1 C36_1 H36_1 119.7 . . ?
C31_1 C36_1 H36_1 119.7 . . ?
C12_2 N11_2 C16_2 120.34(14) . . ?
C12_2 N11_2 O11_2 119.53(14) . . ?
C16_2 N11_2 O11_2 120.13(14) . . ?
N12_2 C12_2 N13_2 121.44(17) . . ?
N12_2 C12_2 N11_2 116.92(15) . . ?
N13_2 C12_2 N11_2 121.64(17) . . ?
C12_2 N12_2 H12A_2 122.8(15) . . ?
C12_2 N12_2 H12B_2 117.4(16) . . ?
H12A_2 N12_2 H12B_2 119(2) . . ?
C12_2 N13_2 C14_2 118.60(16) . . ?
N21_2 C14_2 N13_2 117.14(17) . . ?
N21_2 C14_2 C15_2 121.58(17) . . ?
N13_2 C14_2 C15_2 121.27(15) . . ?
C16_2 C15_2 C14_2 118.75(17) . . ?
C16_2 C15_2 H15_2 120.6 . . ?
C14_2 C15_2 H15_2 120.6 . . ?
N16_2 C16_2 N11_2 116.38(16) . . ?
N16_2 C16_2 C15_2 124.80(18) . . ?
N11_2 C16_2 C15_2 118.82(17) . . ?
C16_2 N16_2 H16A_2 117.1(16) . . ?
C16_2 N16_2 H16B_2 120.1(14) . . ?
H16A_2 N16_2 H16B_2 123(2) . . ?
C14_2 N21_2 C26_2 122.88(16) . . ?
C14_2 N21_2 C22_2 121.44(16) . . ?
C26_2 N21_2 C22_2 112.58(15) . . ?
N21_2 C22_2 C23_2 110.38(18) . . ?
N21_2 C22_2 H22A_2 109.6 . . ?
C23_2 C22_2 H22A_2 109.6 . . ?
N21_2 C22_2 H22B_2 109.6 . . ?
C23_2 C22_2 H22B_2 109.6 . . ?
H22A_2 C22_2 H22B_2 108.1 . . ?
C22_2 C23_2 C24_2 109.61(18) . . ?
C22_2 C23_2 H23A_2 109.7 . . ?
C24_2 C23_2 H23A_2 109.7 . . ?
C22_2 C23_2 H23B_2 109.7 . . ?
C24_2 C23_2 H23B_2 109.7 . . ?
H23A_2 C23_2 H23B_2 108.2 . . ?
C25_2 C24_2 C23_2 110.63(16) . . ?
C25_2 C24_2 H24A_2 109.5 . . ?
C23_2 C24_2 H24A_2 109.5 . . ?
C25_2 C24_2 H24B_2 109.5 . . ?
C23_2 C24_2 H24B_2 109.5 . . ?
H24A_2 C24_2 H24B_2 108.1 . . ?
C24_2 C25_2 C26_2 110.28(17) . . ?
C24_2 C25_2 H25A_2 109.6 . . ?
C26_2 C25_2 H25A_2 109.6 . . ?
C24_2 C25_2 H25B_2 109.6 . . ?
C26_2 C25_2 H25B_2 109.6 . . ?
H25A_2 C25_2 H25B_2 108.1 . . ?
N21_2 C26_2 C25_2 110.32(16) . . ?
N21_2 C26_2 H26A_2 109.6 . . ?
C25_2 C26_2 H26A_2 109.6 . . ?
N21_2 C26_2 H26B_2 109.6 . . ?
C25_2 C26_2 H26B_2 109.6 . . ?
H26A_2 C26_2 H26B_2 108.1 . . ?
C36A_2 C31A_2 C32A_2 118.9(7) . . ?
C36A_2 C31A_2 C37A_2 122.2(7) . . ?
C32A_2 C31A_2 C37A_2 118.4(9) . . ?
O32A_2 C37A_2 O31A_2 122.5(4) . . ?
O32A_2 C37A_2 C31A_2 120.6(5) . . ?
O31A_2 C37A_2 C31A_2 116.9(6) . . ?
C37A_2 O31A_2 H31A_2 109.5 . . ?
C33A_2 C32A_2 C31A_2 123.9(12) . . ?
C33A_2 C32A_2 H32A_2 118.0 . . ?
C31A_2 C32A_2 H32A_2 118.0 . . ?
C32A_2 C33A_2 C34A_2 115.2(12) . . ?
C32A_2 C33A_2 H33A_2 122.4 . . ?
C34A_2 C33A_2 H33A_2 122.4 . . ?
C35A_2 C34A_2 C33A_2 122.0(7) . . ?
C35A_2 C34A_2 H34A_2 119.0 . . ?
C33A_2 C34A_2 H34A_2 119.0 . . ?
C34A_2 C35A_2 C36A_2 120.3(5) . . ?
C34A_2 C35A_2 H35A_2 119.9 . . ?
C36A_2 C35A_2 H35A_2 119.9 . . ?
C31A_2 C36A_2 C35A_2 119.2(6) . . ?
C31A_2 C36A_2 H36A_2 120.4 . . ?
C35A_2 C36A_2 H36A_2 120.4 . . ?
C36B_2 C31B_2 C32B_2 118.8(8) . . ?
C36B_2 C31B_2 C37B_2 122.8(9) . . ?
C32B_2 C31B_2 C37B_2 118.4(8) . . ?
O32B_2 C37B_2 O31B_2 124.1(4) . . ?
O32B_2 C37B_2 C31B_2 121.5(5) . . ?
O31B_2 C37B_2 C31B_2 114.3(5) . . ?
C37B_2 O31B_2 H31B_2 109.5 . . ?
C31B_2 C32B_2 C33B_2 120.4(6) . . ?
C31B_2 C32B_2 H32B_2 119.8 . . ?
C33B_2 C32B_2 H32B_2 119.8 . . ?
C34B_2 C33B_2 C32B_2 117.7(5) . . ?
C34B_2 C33B_2 H33B_2 121.2 . . ?
C32B_2 C33B_2 H33B_2 121.2 . . ?
C35B_2 C34B_2 C33B_2 121.7(8) . . ?
C35B_2 C34B_2 H34B_2 119.2 . . ?
C33B_2 C34B_2 H34B_2 119.2 . . ?
C34B_2 C35B_2 C36B_2 120.1(13) . . ?
C34B_2 C35B_2 H35B_2 120.0 . . ?
C36B_2 C35B_2 H35B_2 120.0 . . ?
C35B_2 C36B_2 C31B_2 120.7(13) . . ?
C35B_2 C36B_2 H36B_2 119.7 . . ?
C31B_2 C36B_2 H36B_2 119.7 . . ?

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
C16_1 N11_1 C12_1 N12_1 175.27(16) . . . . ?
O11_1 N11_1 C12_1 N12_1 -2.7(2) . . . . ?
C16_1 N11_1 C12_1 N13_1 -4.1(2) . . . . ?
O11_1 N11_1 C12_1 N13_1 177.93(14) . . . . ?
N12_1 C12_1 N13_1 C14_1 -178.45(17) . . . . ?
N11_1 C12_1 N13_1 C14_1 0.9(2) . . . . ?
C12_1 N13_1 C14_1 N21_1 -176.56(15) . . . . ?
C12_1 N13_1 C14_1 C15_1 2.9(2) . . . . ?
N21_1 C14_1 C15_1 C16_1 176.06(15) . . . . ?
N13_1 C14_1 C15_1 C16_1 -3.4(2) . . . . ?
C14_1 C15_1 C16_1 N16_1 -178.02(17) . . . . ?
C14_1 C15_1 C16_1 N11_1 0.2(2) . . . . ?
C12_1 N11_1 C16_1 N16_1 -178.10(16) . . . . ?
O11_1 N11_1 C16_1 N16_1 -0.1(2) . . . . ?
C12_1 N11_1 C16_1 C15_1 3.6(2) . . . . ?
O11_1 N11_1 C16_1 C15_1 -178.42(14) . . . . ?
C15_1 C14_1 N21_1 C26_1 11.7(2) . . . . ?
N13_1 C14_1 N21_1 C26_1 -168.81(16) . . . . ?
C15_1 C14_1 N21_1 C22_1 166.07(16) . . . . ?
N13_1 C14_1 N21_1 C22_1 -14.4(3) . . . . ?
C14_1 N21_1 C22_1 C23_1 -96.8(2) . . . . ?
C26_1 N21_1 C22_1 C23_1 59.8(2) . . . . ?
N21_1 C22_1 C23_1 C24_1 -55.2(2) . . . . ?
C22_1 C23_1 C24_1 C25_1 53.4(2) . . . . ?
C23_1 C24_1 C25_1 C26_1 -54.4(2) . . . . ?
C14_1 N21_1 C26_1 C25_1 95.6(2) . . . . ?
C22_1 N21_1 C26_1 C25_1 -61.1(2) . . . . ?
C24_1 C25_1 C26_1 N21_1 57.6(2) . . . . ?
C32_1 C31_1 C37_1 O32_1 -14.6(3) . . . . ?
C36_1 C31_1 C37_1 O32_1 165.17(18) . . . . ?
C32_1 C31_1 C37_1 O31_1 163.86(18) . . . . ?
C36_1 C31_1 C37_1 O31_1 -16.4(3) . . . . ?
C36_1 C31_1 C32_1 C33_1 1.6(3) . . . . ?
C37_1 C31_1 C32_1 C33_1 -178.67(18) . . . . ?
C31_1 C32_1 C33_1 C34_1 -1.7(3) . . . . ?
C32_1 C33_1 C34_1 C35_1 0.8(3) . . . . ?
C33_1 C34_1 C35_1 C36_1 0.2(3) . . . . ?
C34_1 C35_1 C36_1 C31_1 -0.3(3) . . . . ?
C32_1 C31_1 C36_1 C35_1 -0.6(3) . . . . ?
C37_1 C31_1 C36_1 C35_1 179.70(18) . . . . ?
C16_2 N11_2 C12_2 N12_2 -173.56(17) . . . . ?
O11_2 N11_2 C12_2 N12_2 6.6(2) . . . . ?
C16_2 N11_2 C12_2 N13_2 6.2(3) . . . . ?
O11_2 N11_2 C12_2 N13_2 -173.63(15) . . . . ?
N12_2 C12_2 N13_2 C14_2 179.56(17) . . . . ?
N11_2 C12_2 N13_2 C14_2 -0.2(3) . . . . ?
C12_2 N13_2 C14_2 N21_2 172.80(15) . . . . ?
C12_2 N13_2 C14_2 C15_2 -6.2(3) . . . . ?
N21_2 C14_2 C15_2 C16_2 -172.42(16) . . . . ?
N13_2 C14_2 C15_2 C16_2 6.5(3) . . . . ?
C12_2 N11_2 C16_2 N16_2 173.67(17) . . . . ?
O11_2 N11_2 C16_2 N16_2 -6.5(3) . . . . ?
C12_2 N11_2 C16_2 C15_2 -5.7(3) . . . . ?
O11_2 N11_2 C16_2 C15_2 174.14(15) . . . . ?
C14_2 C15_2 C16_2 N16_2 -179.82(18) . . . . ?
C14_2 C15_2 C16_2 N11_2 -0.5(3) . . . . ?
N13_2 C14_2 N21_2 C26_2 167.24(16) . . . . ?
C15_2 C14_2 N21_2 C26_2 -13.8(3) . . . . ?
N13_2 C14_2 N21_2 C22_2 8.6(3) . . . . ?
C15_2 C14_2 N21_2 C22_2 -172.40(18) . . . . ?
C14_2 N21_2 C22_2 C23_2 101.1(2) . . . . ?
C26_2 N21_2 C22_2 C23_2 -59.5(2) . . . . ?
N21_2 C22_2 C23_2 C24_2 57.0(2) . . . . ?
C22_2 C23_2 C24_2 C25_2 -55.9(2) . . . . ?
C23_2 C24_2 C25_2 C26_2 55.4(2) . . . . ?
C14_2 N21_2 C26_2 C25_2 -101.7(2) . . . . ?
C22_2 N21_2 C26_2 C25_2 58.6(2) . . . . ?
C24_2 C25_2 C26_2 N21_2 -55.9(2) . . . . ?
C36A_2 C31A_2 C37A_2 O32A_2 170.1(6) . . . . ?
C32A_2 C31A_2 C37A_2 O32A_2 -2(2) . . . . ?
C36A_2 C31A_2 C37A_2 O31A_2 -8.5(10) . . . . ?
C32A_2 C31A_2 C37A_2 O31A_2 179(2) . . . . ?
C36A_2 C31A_2 C32A_2 C33A_2 -2(5) . . . . ?
C37A_2 C31A_2 C32A_2 C33A_2 170(3) . . . . ?
C31A_2 C32A_2 C33A_2 C34A_2 7(6) . . . . ?
C32A_2 C33A_2 C34A_2 C35A_2 -8(4) . . . . ?
C33A_2 C34A_2 C35A_2 C36A_2 3.4(19) . . . . ?
C32A_2 C31A_2 C36A_2 C35A_2 -2(2) . . . . ?
C37A_2 C31A_2 C36A_2 C35A_2 -174.3(6) . . . . ?
C34A_2 C35A_2 C36A_2 C31A_2 1.9(8) . . . . ?
C36B_2 C31B_2 C37B_2 O32B_2 176(3) . . . . ?
C32B_2 C31B_2 C37B_2 O32B_2 -1.6(10) . . . . ?
C36B_2 C31B_2 C37B_2 O31B_2 -7(3) . . . . ?
C32B_2 C31B_2 C37B_2 O31B_2 174.9(6) . . . . ?
C36B_2 C31B_2 C32B_2 C33B_2 3(3) . . . . ?
C37B_2 C31B_2 C32B_2 C33B_2 -179.1(6) . . . . ?
C31B_2 C32B_2 C33B_2 C34B_2 1.0(9) . . . . ?
C32B_2 C33B_2 C34B_2 C35B_2 -8(2) . . . . ?
C33B_2 C34B_2 C35B_2 C36B_2 10(5) . . . . ?
C34B_2 C35B_2 C36B_2 C31B_2 -6(6) . . . . ?
C32B_2 C31B_2 C36B_2 C35B_2 0(6) . . . . ?
C37B_2 C31B_2 C36B_2 C35B_2 -178(3) . . . . ?

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
N12_1 H12A_1 O11_1 0.84(3) 2.26(3) 2.969(2) 143(2) 2_665
N12_1 H12B_1 O31A_2 0.86(3) 2.23(3) 3.068(3) 164(2) 2_656
N12_1 H12B_1 O32B_2 0.86(3) 1.85(3) 2.693(4) 164(2) 2_656
N16_1 H16A_1 O11_2 0.91(3) 2.13(3) 2.988(3) 157(2) 1_564
N16_1 H16B_1 O32A_2 0.80(3) 2.13(3) 2.827(3) 145(2) 2_666
N12_2 H12A_2 O11_1 0.89(2) 2.10(2) 2.923(2) 153(2) 1_546
N12_2 H12B_2 O32_1 0.83(2) 2.09(3) 2.904(2) 167(2) 2_656
N16_2 H16A_2 O11_2 0.85(2) 2.19(2) 2.936(2) 147(2) 2_657
N16_2 H16B_2 O31_1 0.92(3) 2.19(3) 3.083(2) 163.5(18) 2_666
O31_1 H31_1 O11_1 1.12(2) 1.38(2) 2.4895(16) 175(2) .
O31A_2 H31A_2 O11_2 0.84 1.61 2.442(3) 172.8 .
O31B_2 H31B_2 O11_2 0.84 1.86 2.693(4) 173.6 .

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.929
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.065


