##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-01-12
_journal_date_accepted     2011-01-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o503
_journal_page_last     o504
_journal_paper_category     QO
_journal_coeditor_code     KP2304
_publ_contact_author_name     'Krzysztof Brzezinski'
_publ_contact_author_address
;
Synchrotron Radiation Research Section,
MCL, National Cancer Institute,
Argonne National Laboratory,
Biosciences Division, Bldg. 202, Rm. Q141,
Argonne
IL 60439
USA
;
_publ_contact_author_email     'kbrzezinski@anl.gov'
_publ_contact_author_fax     '1 630 252 3622'
_publ_contact_author_phone     '1 630 252 3961'
_publ_section_title
;
rac-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide from synchrotron
data
;
loop_
    _publ_author_name
    _publ_author_address
    'Brzezinski, Krzysztof'
;
Synchrotron Radiation Research Section,
MCL, National Cancer Institute,
Argonne National Laboratory,
Biosciences Division, Bldg 202,
Argonne
IL 60439
USA
;
    'Dauter, Zbigniew'
;
Synchrotron Radiation Research Section,
MCL, National Cancer Institute,
Argonne National Laboratory,
Biosciences Division, Bldg 202,
Argonne
IL 60439
USA
;
    'Baj, Aneta'
;
Institute of Chemistry,
University of Białystok,
Piłsudskiego 11/4,
15-443 Białystok
Poland
;
    'Wałejko, Piotr'
;
Institute of Chemistry,
University of Białystok,
Piłsudskiego 11/4,
15-443 Białystok
Poland
;
    'Witkowski, Stanisław'
;
Institute of Chemistry,
University of Białystok,
Piłsudskiego 11/4,
15-443 Białystok
Poland
;
data_I
_chemical_name_systematic
;
rac-6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H19 N O3'
_chemical_formula_sum     'C14 H19 N O3'
_chemical_formula_iupac     'C14 H19 N O3'
_chemical_formula_weight     249.31
_chemical_melting_point     492
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     9.110(10)
_cell_length_b     17.92(2)
_cell_length_c     15.950(10)
_cell_angle_alpha     90.00
_cell_angle_beta     100.430(10)
_cell_angle_gamma     90.00
_cell_volume     2561(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     6360
_cell_measurement_theta_min     1.43
_cell_measurement_theta_max     23.51
_cell_measurement_temperature     100(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.2
_exptl_crystal_size_mid     0.05
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.293
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1072
_exptl_absorpt_coefficient_mu     0.057
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SCALEPACK; Otwinowski et al., 2003)'
_exptl_absorpt_correction_T_min     0.988
_exptl_absorpt_correction_T_max     0.997
_exptl_special_details
;
The crystal was mounted with vaseline on a pin attached capillary. Upon
mounting, the crystal was quenched to 100 K in a nitrogen-gas stream supplied
by an Oxford Cryo-Jet. Diffraction data were measured at the station 24-ID---C
of the APS synchrotron by rotation method.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     synchrotron
_diffrn_radiation_wavelength     0.59040
_diffrn_radiation_source     'NECAT 24ID-C synchrotron beamline APS, USA'
_diffrn_radiation_monochromator     'Si111 double crystal'
_diffrn_measurement_device_type     'MAR315 CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     14016
_diffrn_reflns_av_R_equivalents     0.030
_diffrn_reflns_av_sigmaI/netI     0.0364
_diffrn_reflns_theta_min     1.43
_diffrn_reflns_theta_max     23.51
_diffrn_reflns_theta_full     23.51
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.961
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     20
_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 >
2σ(F²) is used only for calculating R-factors 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.
;
_reflns_number_total     6360
_reflns_number_gt     5153
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0615
_refine_ls_R_factor_gt     0.0495
_refine_ls_wR_factor_gt     0.1399
_refine_ls_wR_factor_ref     0.1469
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     6360
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0846P)²+0.4358P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.414
_refine_diff_density_min     -0.246
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' -0.0044 0.0011
                         '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' -0.0044 0.0022
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0030 0.0040
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'NECAT APS beamline software'
_computing_cell_refinement     'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_reduction     'HKL2000 (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SHELXD (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                             'ORTEP-3 (Farrugia, 1997) and PyMOL (DeLano, 2002)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.61019(10) 0.45827(5) 0.16067(5) 0.0245(2) Uani d . 1 . .
    C C2 0.47454(14) 0.45990(7) 0.19461(8) 0.0237(3) Uani d . 1 . .
    C C3 0.34104(15) 0.47162(7) 0.12365(8) 0.0268(3) Uani d . 1 . .
    H H3A 0.3515 0.5198 0.0950 0.032 Uiso calc R 1 . .
    H H3B 0.2487 0.4736 0.1481 0.032 Uiso calc R 1 . .
    C C4 0.32903(14) 0.40842(7) 0.05855(8) 0.0247(3) Uani d . 1 . .
    H H4A 0.2887 0.3633 0.0822 0.030 Uiso calc R 1 . .
    H H4B 0.2587 0.4231 0.0063 0.030 Uiso calc R 1 . .
    C C5 0.48962(14) 0.34738(7) -0.03638(8) 0.0231(3) Uani d . 1 . .
    C C6 0.62994(14) 0.33351(7) -0.05616(8) 0.0235(3) Uani d . 1 . .
    C C7 0.76145(14) 0.36122(7) -0.00604(8) 0.0232(3) Uani d . 1 . .
    C C8 0.75096(14) 0.40469(7) 0.06572(8) 0.0224(2) Uani d . 1 . .
    C C9 0.61017(14) 0.41713(6) 0.08636(7) 0.0215(2) Uani d . 1 . .
    C C10 0.47925(14) 0.39050(7) 0.03598(8) 0.0217(2) Uani d . 1 . .
    C C11 0.45591(14) 0.38690(7) 0.24307(8) 0.0233(3) Uani d . 1 . .
    O O12 0.33708(11) 0.37440(5) 0.26791(6) 0.0303(2) Uani d . 1 . .
    N N13 0.57098(13) 0.34076(6) 0.25872(7) 0.0271(2) Uani d . 1 . .
    H H13A 0.5647 0.2995 0.2877 0.033 Uiso calc R 1 . .
    H H13B 0.6538 0.3514 0.2401 0.033 Uiso calc R 1 . .
    C C14 0.49388(17) 0.52489(7) 0.25803(9) 0.0312(3) Uani d . 1 . .
    H H14A 0.4095 0.5259 0.2884 0.047 Uiso calc R 1 . .
    H H14B 0.4975 0.5720 0.2272 0.047 Uiso calc R 1 . .
    H H14C 0.5870 0.5184 0.2991 0.047 Uiso calc R 1 . .
    C C15 0.35081(15) 0.31770(8) -0.09261(9) 0.0299(3) Uani d . 1 . .
    H H15A 0.3000 0.3584 -0.1274 0.045 Uiso calc R 1 . .
    H H15B 0.2838 0.2968 -0.0570 0.045 Uiso calc R 1 . .
    H H15C 0.3784 0.2787 -0.1299 0.045 Uiso calc R 1 . .
    O O16 0.63187(11) 0.29210(6) -0.12892(6) 0.0325(2) Uani d . 1 . .
    H H16A 0.7183 0.2925 -0.1404 0.049 Uiso calc R 1 . .
    C C17 0.91159(15) 0.34490(8) -0.02946(9) 0.0304(3) Uani d . 1 . .
    H H17A 0.9123 0.2938 -0.0513 0.046 Uiso calc R 1 . .
    H H17B 0.9898 0.3502 0.0212 0.046 Uiso calc R 1 . .
    H H17C 0.9301 0.3801 -0.0734 0.046 Uiso calc R 1 . .
    C C18 0.88847(15) 0.43836(8) 0.12025(9) 0.0302(3) Uani d . 1 . .
    H H18A 0.8581 0.4729 0.1615 0.045 Uiso calc R 1 . .
    H H18B 0.9462 0.4654 0.0838 0.045 Uiso calc R 1 . .
    H H18C 0.9500 0.3985 0.1507 0.045 Uiso calc R 1 . .
    O O21 0.09463(10) 0.20376(5) 0.15518(6) 0.0261(2) Uani d . 1 . .
    C C22 -0.03768(14) 0.18816(7) 0.18944(8) 0.0246(3) Uani d . 1 . .
    C C23 -0.17485(14) 0.19491(8) 0.11915(9) 0.0277(3) Uani d . 1 . .
    H H23A -0.1817 0.2464 0.0963 0.033 Uiso calc R 1 . .
    H H23B -0.2658 0.1849 0.1431 0.033 Uiso calc R 1 . .
    C C24 -0.16637(14) 0.13979(8) 0.04698(9) 0.0278(3) Uani d . 1 . .
    H H24A -0.2001 0.0901 0.0629 0.033 Uiso calc R 1 . .
    H H24B -0.2350 0.1563 -0.0051 0.033 Uiso calc R 1 . .
    C C25 0.01411(14) 0.09450(7) -0.04523(8) 0.0242(3) Uani d . 1 . .
    C C26 0.16025(14) 0.08797(7) -0.06026(8) 0.0244(3) Uani d . 1 . .
    C C27 0.28233(14) 0.11907(7) -0.00506(8) 0.0236(3) Uani d . 1 . .
    C C28 0.25737(14) 0.15918(7) 0.06677(8) 0.0229(3) Uani d . 1 . .
    C C29 0.11127(14) 0.16416(7) 0.08231(8) 0.0228(3) Uani d . 1 . .
    C C30 -0.01047(14) 0.13307(7) 0.02768(8) 0.0235(3) Uani d . 1 . .
    C C31 -0.04526(15) 0.24820(7) 0.25651(8) 0.0270(3) Uani d . 1 . .
    O O32 -0.15782(11) 0.25283(6) 0.28939(6) 0.0353(2) Uani d . 1 . .
    N N33 0.07066(14) 0.29294(7) 0.27773(8) 0.0360(3) Uani d . 1 . .
    H H33A 0.0696 0.3277 0.3166 0.043 Uiso calc R 1 . .
    H H33B 0.1490 0.2880 0.2530 0.043 Uiso calc R 1 . .
    C C34 -0.02493(16) 0.11133(7) 0.23290(9) 0.0300(3) Uani d . 1 . .
    H H34A -0.1073 0.1049 0.2642 0.045 Uiso calc R 1 . .
    H H34B 0.0704 0.1079 0.2727 0.045 Uiso calc R 1 . .
    H H34C -0.0298 0.0722 0.1896 0.045 Uiso calc R 1 . .
    C C35 -0.11451(15) 0.06001(8) -0.10581(8) 0.0291(3) Uani d . 1 . .
    H H35A -0.0827 0.0480 -0.1597 0.044 Uiso calc R 1 . .
    H H35B -0.1979 0.0954 -0.1164 0.044 Uiso calc R 1 . .
    H H35C -0.1465 0.0143 -0.0806 0.044 Uiso calc R 1 . .
    O O36 0.17961(12) 0.04723(6) -0.13154(6) 0.0315(2) Uani d . 1 . .
    H H36A 0.2416 0.0691 -0.1561 0.047 Uiso calc R 1 . .
    C C37 0.43909(15) 0.10894(8) -0.02105(9) 0.0294(3) Uani d . 1 . .
    H H37A 0.4698 0.1537 -0.0486 0.044 Uiso calc R 1 . .
    H H37B 0.4426 0.0657 -0.0582 0.044 Uiso calc R 1 . .
    H H37C 0.5069 0.1008 0.0333 0.044 Uiso calc R 1 . .
    C C38 0.38410(14) 0.19683(7) 0.12563(8) 0.0268(3) Uani d . 1 . .
    H H38A 0.4358 0.2309 0.0927 0.040 Uiso calc R 1 . .
    H H38B 0.4543 0.1590 0.1532 0.040 Uiso calc R 1 . .
    H H38C 0.3445 0.2250 0.1692 0.040 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s are estimated using the full covariance matrix. The cell e.s.d.'s
are taken into account individually in the estimation of e.s.d.'s in
distances, angles and torsion angles; correlations between e.s.d.'s in cell
parameters are only used when they are defined by crystal symmetry. An
approximate (isotropic) treatment of cell e.s.d.'s is used for estimating
e.s.d.'s involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C9 . 1.3958(18) ?
    O1 C2 . 1.4364(19) ?
    C2 C3 . 1.518(2) ?
    C2 C14 . 1.532(2) ?
    C2 C11 . 1.544(2) ?
    C3 C4 . 1.527(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C10 . 1.511(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.393(2) ?
    C5 C10 . 1.406(2) ?
    C5 C15 . 1.509(2) ?
    C6 O16 . 1.3803(18) ?
    C6 C7 . 1.405(2) ?
    C7 C8 . 1.402(2) ?
    C7 C17 . 1.510(2) ?
    C8 C9 . 1.399(2) ?
    C8 C18 . 1.515(2) ?
    C9 C10 . 1.396(2) ?
    C11 O12 . 1.2387(18) ?
    C11 N13 . 1.3230(19) ?
    N13 H13A . 0.8800 ?
    N13 H13B . 0.8800 ?
    C14 H14A . 0.9800 ?
    C14 H14B . 0.9800 ?
    C14 H14C . 0.9800 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    O16 H16A . 0.8400 ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C18 H18A . 0.9800 ?
    C18 H18B . 0.9800 ?
    C18 H18C . 0.9800 ?
    O21 C29 . 1.3933(18) ?
    O21 C22 . 1.4381(18) ?
    C22 C23 . 1.525(2) ?
    C22 C31 . 1.527(2) ?
    C22 C34 . 1.536(2) ?
    C23 C24 . 1.529(2) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 C30 . 1.511(2) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C25 C26 . 1.400(2) ?
    C25 C30 . 1.405(2) ?
    C25 C35 . 1.510(2) ?
    C26 O36 . 1.3889(18) ?
    C26 C27 . 1.403(2) ?
    C27 C28 . 1.406(2) ?
    C27 C37 . 1.506(2) ?
    C28 C29 . 1.400(2) ?
    C28 C38 . 1.509(2) ?
    C29 C30 . 1.396(2) ?
    C31 O32 . 1.2362(18) ?
    C31 N33 . 1.320(2) ?
    N33 H33A . 0.8800 ?
    N33 H33B . 0.8800 ?
    C34 H34A . 0.9800 ?
    C34 H34B . 0.9800 ?
    C34 H34C . 0.9800 ?
    C35 H35A . 0.9800 ?
    C35 H35B . 0.9800 ?
    C35 H35C . 0.9800 ?
    O36 H36A . 0.8400 ?
    C37 H37A . 0.9800 ?
    C37 H37B . 0.9800 ?
    C37 H37C . 0.9800 ?
    C38 H38A . 0.9800 ?
    C38 H38B . 0.9800 ?
    C38 H38C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C9 O1 C2 . . 117.57(9) ?
    O1 C2 C3 . . 110.46(12) ?
    O1 C2 C14 . . 105.09(11) ?
    C3 C2 C14 . . 111.59(11) ?
    O1 C2 C11 . . 110.57(10) ?
    C3 C2 C11 . . 110.15(11) ?
    C14 C2 C11 . . 108.87(12) ?
    C2 C3 C4 . . 110.69(11) ?
    C2 C3 H3A . . 109.5 ?
    C4 C3 H3A . . 109.5 ?
    C2 C3 H3B . . 109.5 ?
    C4 C3 H3B . . 109.5 ?
    H3A C3 H3B . . 108.1 ?
    C10 C4 C3 . . 111.29(11) ?
    C10 C4 H4A . . 109.4 ?
    C3 C4 H4A . . 109.4 ?
    C10 C4 H4B . . 109.4 ?
    C3 C4 H4B . . 109.4 ?
    H4A C4 H4B . . 108.0 ?
    C6 C5 C10 . . 118.98(11) ?
    C6 C5 C15 . . 120.47(12) ?
    C10 C5 C15 . . 120.54(12) ?
    O16 C6 C5 . . 115.99(11) ?
    O16 C6 C7 . . 121.94(12) ?
    C5 C6 C7 . . 122.06(13) ?
    C8 C7 C6 . . 118.93(12) ?
    C8 C7 C17 . . 120.54(11) ?
    C6 C7 C17 . . 120.53(13) ?
    C9 C8 C7 . . 118.79(11) ?
    C9 C8 C18 . . 119.98(12) ?
    C7 C8 C18 . . 121.23(12) ?
    O1 C9 C8 . . 115.15(11) ?
    O1 C9 C10 . . 122.55(11) ?
    C8 C9 C10 . . 122.30(12) ?
    C9 C10 C5 . . 118.88(12) ?
    C9 C10 C4 . . 120.42(12) ?
    C5 C10 C4 . . 120.70(11) ?
    O12 C11 N13 . . 122.36(13) ?
    O12 C11 C2 . . 119.66(11) ?
    N13 C11 C2 . . 117.95(12) ?
    C11 N13 H13A . . 120.0 ?
    C11 N13 H13B . . 120.0 ?
    H13A N13 H13B . . 120.0 ?
    C2 C14 H14A . . 109.5 ?
    C2 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C2 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C5 C15 H15A . . 109.5 ?
    C5 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C5 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C6 O16 H16A . . 109.5 ?
    C7 C17 H17A . . 109.5 ?
    C7 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C7 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    C8 C18 H18A . . 109.5 ?
    C8 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C8 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    C29 O21 C22 . . 116.31(10) ?
    O21 C22 C23 . . 109.68(12) ?
    O21 C22 C31 . . 106.05(10) ?
    C23 C22 C31 . . 108.91(11) ?
    O21 C22 C34 . . 110.22(10) ?
    C23 C22 C34 . . 112.81(11) ?
    C31 C22 C34 . . 108.94(12) ?
    C22 C23 C24 . . 110.84(11) ?
    C22 C23 H23A . . 109.5 ?
    C24 C23 H23A . . 109.5 ?
    C22 C23 H23B . . 109.5 ?
    C24 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 108.1 ?
    C30 C24 C23 . . 112.47(11) ?
    C30 C24 H24A . . 109.1 ?
    C23 C24 H24A . . 109.1 ?
    C30 C24 H24B . . 109.1 ?
    C23 C24 H24B . . 109.1 ?
    H24A C24 H24B . . 107.8 ?
    C26 C25 C30 . . 118.81(11) ?
    C26 C25 C35 . . 120.54(13) ?
    C30 C25 C35 . . 120.64(12) ?
    O36 C26 C25 . . 116.73(11) ?
    O36 C26 C27 . . 121.25(12) ?
    C25 C26 C27 . . 121.99(13) ?
    C28 C27 C26 . . 119.20(12) ?
    C28 C27 C37 . . 119.85(11) ?
    C26 C27 C37 . . 120.93(13) ?
    C29 C28 C27 . . 118.43(11) ?
    C29 C28 C38 . . 120.41(12) ?
    C27 C28 C38 . . 121.16(12) ?
    O21 C29 C30 . . 121.98(12) ?
    O21 C29 C28 . . 115.50(11) ?
    C30 C29 C28 . . 122.50(13) ?
    C29 C30 C25 . . 119.02(12) ?
    C29 C30 C24 . . 120.70(12) ?
    C25 C30 C24 . . 120.28(11) ?
    O32 C31 N33 . . 122.47(14) ?
    O32 C31 C22 . . 119.38(12) ?
    N33 C31 C22 . . 118.15(12) ?
    C31 N33 H33A . . 120.0 ?
    C31 N33 H33B . . 120.0 ?
    H33A N33 H33B . . 120.0 ?
    C22 C34 H34A . . 109.5 ?
    C22 C34 H34B . . 109.5 ?
    H34A C34 H34B . . 109.5 ?
    C22 C34 H34C . . 109.5 ?
    H34A C34 H34C . . 109.5 ?
    H34B C34 H34C . . 109.5 ?
    C25 C35 H35A . . 109.5 ?
    C25 C35 H35B . . 109.5 ?
    H35A C35 H35B . . 109.5 ?
    C25 C35 H35C . . 109.5 ?
    H35A C35 H35C . . 109.5 ?
    H35B C35 H35C . . 109.5 ?
    C26 O36 H36A . . 109.5 ?
    C27 C37 H37A . . 109.5 ?
    C27 C37 H37B . . 109.5 ?
    H37A C37 H37B . . 109.5 ?
    C27 C37 H37C . . 109.5 ?
    H37A C37 H37C . . 109.5 ?
    H37B C37 H37C . . 109.5 ?
    C28 C38 H38A . . 109.5 ?
    C28 C38 H38B . . 109.5 ?
    H38A C38 H38B . . 109.5 ?
    C28 C38 H38C . . 109.5 ?
    H38A C38 H38C . . 109.5 ?
    H38B C38 H38C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C9 O1 C2 C3 . . . . -43.88(14) ?
    C9 O1 C2 C14 . . . . -164.37(10) ?
    C9 O1 C2 C11 . . . . 78.31(14) ?
    O1 C2 C3 C4 . . . . 60.30(13) ?
    C14 C2 C3 C4 . . . . 176.82(11) ?
    C11 C2 C3 C4 . . . . -62.14(14) ?
    C2 C3 C4 C10 . . . . -44.86(15) ?
    C10 C5 C6 O16 . . . . -178.75(10) ?
    C15 C5 C6 O16 . . . . 0.21(17) ?
    C10 C5 C6 C7 . . . . 0.03(18) ?
    C15 C5 C6 C7 . . . . 178.99(11) ?
    O16 C6 C7 C8 . . . . 178.19(11) ?
    C5 C6 C7 C8 . . . . -0.53(18) ?
    O16 C6 C7 C17 . . . . -1.37(18) ?
    C5 C6 C7 C17 . . . . 179.92(12) ?
    C6 C7 C8 C9 . . . . 1.86(17) ?
    C17 C7 C8 C9 . . . . -178.58(11) ?
    C6 C7 C8 C18 . . . . -177.76(11) ?
    C17 C7 C8 C18 . . . . 1.80(18) ?
    C2 O1 C9 C8 . . . . -167.53(10) ?
    C2 O1 C9 C10 . . . . 12.70(16) ?
    C7 C8 C9 O1 . . . . 177.40(10) ?
    C18 C8 C9 O1 . . . . -2.97(16) ?
    C7 C8 C9 C10 . . . . -2.83(18) ?
    C18 C8 C9 C10 . . . . 176.80(11) ?
    O1 C9 C10 C5 . . . . -177.91(10) ?
    C8 C9 C10 C5 . . . . 2.34(18) ?
    O1 C9 C10 C4 . . . . 2.66(17) ?
    C8 C9 C10 C4 . . . . -177.10(11) ?
    C6 C5 C10 C9 . . . . -0.90(17) ?
    C15 C5 C10 C9 . . . . -179.86(11) ?
    C6 C5 C10 C4 . . . . 178.53(11) ?
    C15 C5 C10 C4 . . . . -0.43(18) ?
    C3 C4 C10 C9 . . . . 14.64(16) ?
    C3 C4 C10 C5 . . . . -164.78(11) ?
    O1 C2 C11 O12 . . . . -171.35(11) ?
    C3 C2 C11 O12 . . . . -48.97(16) ?
    C14 C2 C11 O12 . . . . 73.68(15) ?
    O1 C2 C11 N13 . . . . 10.66(15) ?
    C3 C2 C11 N13 . . . . 133.04(13) ?
    C14 C2 C11 N13 . . . . -104.31(13) ?
    C29 O21 C22 C23 . . . . -51.64(14) ?
    C29 O21 C22 C31 . . . . -169.10(10) ?
    C29 O21 C22 C34 . . . . 73.14(14) ?
    O21 C22 C23 C24 . . . . 59.96(14) ?
    C31 C22 C23 C24 . . . . 175.62(10) ?
    C34 C22 C23 C24 . . . . -63.30(15) ?
    C22 C23 C24 C30 . . . . -39.37(15) ?
    C30 C25 C26 O36 . . . . 177.90(11) ?
    C35 C25 C26 O36 . . . . -1.46(17) ?
    C30 C25 C26 C27 . . . . -0.36(18) ?
    C35 C25 C26 C27 . . . . -179.72(11) ?
    O36 C26 C27 C28 . . . . -179.33(11) ?
    C25 C26 C27 C28 . . . . -1.15(18) ?
    O36 C26 C27 C37 . . . . -0.33(18) ?
    C25 C26 C27 C37 . . . . 177.85(12) ?
    C26 C27 C28 C29 . . . . 2.41(17) ?
    C37 C27 C28 C29 . . . . -176.60(11) ?
    C26 C27 C28 C38 . . . . -176.99(11) ?
    C37 C27 C28 C38 . . . . 4.00(18) ?
    C22 O21 C29 C30 . . . . 22.81(16) ?
    C22 O21 C29 C28 . . . . -158.56(11) ?
    C27 C28 C29 O21 . . . . 179.10(10) ?
    C38 C28 C29 O21 . . . . -1.49(17) ?
    C27 C28 C29 C30 . . . . -2.28(18) ?
    C38 C28 C29 C30 . . . . 177.13(11) ?
    O21 C29 C30 C25 . . . . 179.31(11) ?
    C28 C29 C30 C25 . . . . 0.78(18) ?
    O21 C29 C30 C24 . . . . -1.47(18) ?
    C28 C29 C30 C24 . . . . 179.99(11) ?
    C26 C25 C30 C29 . . . . 0.56(18) ?
    C35 C25 C30 C29 . . . . 179.91(11) ?
    C26 C25 C30 C24 . . . . -178.66(11) ?
    C35 C25 C30 C24 . . . . 0.69(18) ?
    C23 C24 C30 C29 . . . . 11.06(17) ?
    C23 C24 C30 C25 . . . . -169.73(11) ?
    O21 C22 C31 O32 . . . . 171.96(11) ?
    C23 C22 C31 O32 . . . . 53.99(16) ?
    C34 C22 C31 O32 . . . . -69.42(15) ?
    O21 C22 C31 N33 . . . . -8.72(16) ?
    C23 C22 C31 N33 . . . . -126.69(14) ?
    C34 C22 C31 N33 . . . . 109.89(14) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N13 H13A O16 4_566 0.88 2.13 2.971(2) 160
    N13 H13B O32 1_655 0.88 2.49 2.896(3) 109
    O16 H16A O32 4_665 0.84 1.91 2.631(2) 143
    N33 H33B O12 1_555 0.88 2.29 2.861(3) 123
    N33 H33A O36 4_566 0.88 2.53 3.281(3) 143
    O36 H36A O12 4_565 0.84 1.91 2.727(2) 165
