##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 992239'
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2014-03-05
_journal_date_accepted     2014-03-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      4
_journal_page_first     o464
_journal_page_last     o464
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814005972
_journal_coeditor_code     IS5346
_publ_contact_author_name
;
 Dongsoo Koh
;
_publ_contact_author_address
;
 Department of Applied Chemistry,
 Dongduk Women's University,
 Seoul 136-714, Republic of Korea
;
_publ_contact_author_email     dskoh@dongduk.ac.kr
_publ_contact_author_fax     82-2-940-4512
_publ_contact_author_phone     82-10-3999-4512
_publ_section_title
;
3-Methoxy-2-[5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]phenol
;
loop_
    _publ_author_name
    _publ_author_address
    'Koh, Dongsoo'
;
Department of Applied Chemistry,
Dongduk Women's University,
Seoul 136-714, Republic of Korea
;
    'Lim, Yoongho'
;
Division of Bioscience and Biotechnology,
BMIC, Konkuk University,
Seoul 143-701, Republic of Korea
;
    'Lough, Alan J.'
;
Department of Chemistry,
University of Toronto,
Toronto, Ontario, Canada M5S 3H6
;
_chemical_name_systematic
;
3-Methoxy-2-[5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-3-yl]phenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H18 N2 O2'
_chemical_formula_sum     'C20 H18 N2 O2'
_chemical_formula_iupac     'C20 H18 N2 O2'
_chemical_formula_weight     318.36
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 2/c'
_symmetry_space_group_name_Hall     '-P 2yc'
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     21.0215(15)
_cell_length_b     5.6564(5)
_cell_length_c     28.785(2)
_cell_angle_alpha     90.00
_cell_angle_beta     110.543(3)
_cell_angle_gamma     90.00
_cell_volume     3205.1(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     857
_cell_measurement_theta_min     3.28
_cell_measurement_theta_max     56.54
_cell_measurement_temperature     147(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.17
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.07
_exptl_crystal_density_diffrn     1.320
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1344
_exptl_absorpt_coefficient_mu     0.690
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2012)'
_exptl_absorpt_correction_T_min     0.6950
_exptl_absorpt_correction_T_max     0.7528
_exptl_special_details     ?
_diffrn_ambient_temperature     147(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Bruker ImuS'
_diffrn_radiation_monochromator     'multi-layer optics'
_diffrn_measurement_device_type     'Bruker Kappa APEX DUO CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     43387
_diffrn_reflns_av_R_equivalents     0.0450
_diffrn_reflns_av_sigmaI/netI     0.0321
_diffrn_reflns_theta_min     2.24
_diffrn_reflns_theta_max     66.84
_diffrn_reflns_theta_full     66.84
_diffrn_measured_fraction_theta_max     0.968
_diffrn_measured_fraction_theta_full     0.968
_diffrn_reflns_limit_h_min     -24
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -33
_diffrn_reflns_limit_l_max     33
_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 >
σ(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.
;
_reflns_number_total     5506
_reflns_number_gt     4776
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0424
_refine_ls_R_factor_gt     0.0365
_refine_ls_wR_factor_gt     0.0941
_refine_ls_wR_factor_ref     0.0971
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     5506
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0508P)²+0.6182P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.167
_refine_diff_density_min     -0.197
_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' 0.0181 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'
_computing_data_collection     'APEX2 (Bruker, 2012)'
_computing_cell_refinement     'SAINT (Bruker, 2012)'
_computing_data_reduction     'SAINT (Bruker, 2012)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXTL (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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1A 0.49628(5) 0.5886(2) 0.56791(4) 0.0409(3) Uani d . 1 1 . .
    O O2A 0.34244(6) 1.2274(2) 0.54722(4) 0.0440(3) Uani d . 1 1 . .
    N N1A 0.41312(6) 0.7105(2) 0.48182(4) 0.0315(3) Uani d . 1 1 . .
    N N2A 0.38431(6) 0.7224(2) 0.42980(4) 0.0326(3) Uani d . 1 1 . .
    C C1A 0.39789(6) 0.8982(2) 0.50121(5) 0.0246(3) Uani d . 1 1 . .
    C C2A 0.35765(6) 1.0709(2) 0.46192(5) 0.0254(3) Uani d . 1 1 . .
    H H2AA 0.3748 1.2344 0.4698 0.030 Uiso calc R 1 1 . .
    H H2AB 0.3087 1.0666 0.4572 0.030 Uiso calc R 1 1 . .
    C C3A 0.37111(6) 0.9740(2) 0.41647(5) 0.0277(3) Uani d . 1 1 . .
    H H3AA 0.4136 1.0476 0.4149 0.033 Uiso calc R 1 1 . .
    C C4A 0.31402(6) 1.0150(2) 0.36773(5) 0.0252(3) Uani d . 1 1 . .
    C C5A 0.31489(7) 1.2249(2) 0.34150(5) 0.0297(3) Uani d . 1 1 . .
    H H5AA 0.3516 1.3323 0.3544 0.036 Uiso calc R 1 1 . .
    C C6A 0.26385(7) 1.2767(2) 0.29782(5) 0.0304(3) Uani d . 1 1 . .
    H H6AA 0.2657 1.4192 0.2809 0.036 Uiso calc R 1 1 . .
    C C7A 0.20822(7) 1.1210(2) 0.27751(5) 0.0267(3) Uani d . 1 1 . .
    C C8A 0.15504(7) 1.1653(3) 0.23166(5) 0.0335(3) Uani d . 1 1 . .
    H H8AA 0.1560 1.3055 0.2137 0.040 Uiso calc R 1 1 . .
    C C9A 0.10281(7) 1.0100(3) 0.21309(5) 0.0379(4) Uani d . 1 1 . .
    H H9AA 0.0679 1.0421 0.1823 0.045 Uiso calc R 1 1 . .
    C C10A 0.10019(7) 0.8025(3) 0.23919(5) 0.0361(3) Uani d . 1 1 . .
    H H10A 0.0632 0.6961 0.2261 0.043 Uiso calc R 1 1 . .
    C C11A 0.15082(7) 0.7530(3) 0.28344(5) 0.0305(3) Uani d . 1 1 . .
    H H11A 0.1485 0.6122 0.3008 0.037 Uiso calc R 1 1 . .
    C C12A 0.20652(6) 0.9091(2) 0.30362(5) 0.0250(3) Uani d . 1 1 . .
    C C13A 0.26073(6) 0.8605(2) 0.34863(5) 0.0249(3) Uani d . 1 1 . .
    H H13A 0.2602 0.7180 0.3659 0.030 Uiso calc R 1 1 . .
    C C14A 0.42050(6) 0.9222(2) 0.55531(5) 0.0267(3) Uani d . 1 1 . .
    C C15A 0.39484(7) 1.0994(3) 0.57825(5) 0.0312(3) Uani d . 1 1 . .
    C C16A 0.42105(7) 1.1334(3) 0.62929(5) 0.0381(4) Uani d . 1 1 . .
    H H16A 0.4040 1.2561 0.6442 0.046 Uiso calc R 1 1 . .
    C C17A 0.47218(7) 0.9862(3) 0.65800(5) 0.0440(4) Uani d . 1 1 . .
    H H17A 0.4907 1.0107 0.6928 0.053 Uiso calc R 1 1 . .
    C C18A 0.49680(7) 0.8056(3) 0.63740(6) 0.0437(4) Uani d . 1 1 . .
    H H18A 0.5315 0.7049 0.6579 0.052 Uiso calc R 1 1 . .
    C C19A 0.47060(6) 0.7707(3) 0.58629(5) 0.0320(3) Uani d . 1 1 . .
    C C20A 0.31232(10) 1.4005(3) 0.56934(6) 0.0507(5) Uani d . 1 1 . .
    H H20A 0.2743 1.4766 0.5435 0.076 Uiso calc R 1 1 . .
    H H20B 0.3463 1.5199 0.5863 0.076 Uiso calc R 1 1 . .
    H H20C 0.2957 1.3235 0.5934 0.076 Uiso calc R 1 1 . .
    O O1B -0.09997(5) -0.95204(18) 0.51393(4) 0.0354(2) Uani d . 1 1 . .
    O O2B -0.06378(5) -0.28470(19) 0.62119(4) 0.0374(3) Uani d . 1 1 . .
    N N1B 0.01760(6) -0.7754(2) 0.55421(5) 0.0369(3) Uani d . 1 1 . .
    N N2B 0.08805(6) -0.7481(2) 0.56768(5) 0.0386(3) Uani d . 1 1 . .
    C C1B -0.00720(6) -0.6051(2) 0.57246(5) 0.0272(3) Uani d . 1 1 . .
    C C2B 0.04742(6) -0.4300(2) 0.59985(5) 0.0273(3) Uani d . 1 1 . .
    H H2BA 0.0617 -0.4504 0.6362 0.033 Uiso calc R 1 1 . .
    H H2BB 0.0323 -0.2649 0.5911 0.033 Uiso calc R 1 1 . .
    C C3B 0.10441(6) -0.4987(3) 0.58063(5) 0.0302(3) Uani d . 1 1 . .
    H H3BA 0.0992 -0.4067 0.5498 0.036 Uiso calc R 1 1 . .
    C C4B 0.17604(6) -0.4685(2) 0.61734(5) 0.0254(3) Uani d . 1 1 . .
    C C5B 0.21368(7) -0.2659(2) 0.61442(5) 0.0299(3) Uani d . 1 1 . .
    H H5BA 0.1936 -0.1499 0.5897 0.036 Uiso calc R 1 1 . .
    C C6B 0.27874(7) -0.2345(2) 0.64672(5) 0.0305(3) Uani d . 1 1 . .
    H H6BA 0.3032 -0.0968 0.6441 0.037 Uiso calc R 1 1 . .
    C C7B 0.31015(6) -0.4033(2) 0.68385(5) 0.0257(3) Uani d . 1 1 . .
    C C8B 0.37838(7) -0.3815(3) 0.71720(5) 0.0336(3) Uani d . 1 1 . .
    H H8BA 0.4044 -0.2473 0.7151 0.040 Uiso calc R 1 1 . .
    C C9B 0.40695(7) -0.5509(3) 0.75216(5) 0.0365(4) Uani d . 1 1 . .
    H H9BA 0.4528 -0.5350 0.7737 0.044 Uiso calc R 1 1 . .
    C C10B 0.36893(7) -0.7484(3) 0.75651(5) 0.0349(3) Uani d . 1 1 . .
    H H10B 0.3887 -0.8631 0.7815 0.042 Uiso calc R 1 1 . .
    C C11B 0.30344(7) -0.7755(3) 0.72472(5) 0.0294(3) Uani d . 1 1 . .
    H H11B 0.2783 -0.9107 0.7277 0.035 Uiso calc R 1 1 . .
    C C12B 0.27239(6) -0.6065(2) 0.68752(5) 0.0234(3) Uani d . 1 1 . .
    C C13B 0.20506(6) -0.6342(2) 0.65330(5) 0.0249(3) Uani d . 1 1 . .
    H H13B 0.1797 -0.7702 0.6554 0.030 Uiso calc R 1 1 . .
    C C14B -0.07952(6) -0.6070(2) 0.56665(5) 0.0260(3) Uani d . 1 1 . .
    C C15B -0.10804(6) -0.4417(3) 0.59036(5) 0.0289(3) Uani d . 1 1 . .
    C C16B -0.17715(7) -0.4442(3) 0.58272(5) 0.0328(3) Uani d . 1 1 . .
    H H16B -0.1959 -0.3304 0.5985 0.039 Uiso calc R 1 1 . .
    C C17B -0.21851(7) -0.6140(3) 0.55187(5) 0.0362(3) Uani d . 1 1 . .
    H H17B -0.2658 -0.6137 0.5464 0.043 Uiso calc R 1 1 . .
    C C18B -0.19260(7) -0.7822(3) 0.52909(5) 0.0344(3) Uani d . 1 1 . .
    H H18B -0.2215 -0.8983 0.5084 0.041 Uiso calc R 1 1 . .
    C C19B -0.12339(7) -0.7809(3) 0.53664(5) 0.0293(3) Uani d . 1 1 . .
    C C20B -0.09006(7) -0.1221(3) 0.64781(6) 0.0381(4) Uani d . 1 1 . .
    H H20D -0.0534 -0.0195 0.6683 0.057 Uiso calc R 1 1 . .
    H H20E -0.1093 -0.2096 0.6691 0.057 Uiso calc R 1 1 . .
    H H20F -0.1256 -0.0254 0.6243 0.057 Uiso calc R 1 1 . .
    H H1OA 0.4697(11) 0.574(4) 0.5327(9) 0.078(7) Uiso d . 1 1 . .
    H H1OB -0.0542(11) -0.935(4) 0.5237(8) 0.069(6) Uiso d . 1 1 . .
    H H2NA 0.4147(8) 0.653(3) 0.4179(6) 0.043(5) Uiso d . 1 1 . .
    H H2NB 0.1010(8) -0.803(3) 0.5426(7) 0.049(5) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
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
    O1A C19A . 1.3539(19) ?
    O1A H1OA . 0.97(2) ?
    O2A C15A . 1.3582(17) ?
    O2A C20A . 1.4313(18) ?
    N1A C1A . 1.2910(18) ?
    N1A N2A . 1.4059(16) ?
    N2A C3A . 1.4745(18) ?
    N2A H2NA . 0.914(18) ?
    C1A C14A . 1.4664(18) ?
    C1A C2A . 1.5091(18) ?
    C2A C3A . 1.5338(18) ?
    C2A H2AA . 0.9900 ?
    C2A H2AB . 0.9900 ?
    C3A C4A . 1.5104(18) ?
    C3A H3AA . 1.0000 ?
    C4A C13A . 1.3742(19) ?
    C4A C5A . 1.4104(19) ?
    C5A C6A . 1.368(2) ?
    C5A H5AA . 0.9500 ?
    C6A C7A . 1.416(2) ?
    C6A H6AA . 0.9500 ?
    C7A C8A . 1.4210(19) ?
    C7A C12A . 1.4218(19) ?
    C8A C9A . 1.361(2) ?
    C8A H8AA . 0.9500 ?
    C9A C10A . 1.405(2) ?
    C9A H9AA . 0.9500 ?
    C10A C11A . 1.372(2) ?
    C10A H10A . 0.9500 ?
    C11A C12A . 1.4181(19) ?
    C11A H11A . 0.9500 ?
    C12A C13A . 1.4200(18) ?
    C13A H13A . 0.9500 ?
    C14A C19A . 1.4070(19) ?
    C14A C15A . 1.408(2) ?
    C15A C16A . 1.390(2) ?
    C16A C17A . 1.381(2) ?
    C16A H16A . 0.9500 ?
    C17A C18A . 1.371(3) ?
    C17A H17A . 0.9500 ?
    C18A C19A . 1.392(2) ?
    C18A H18A . 0.9500 ?
    C20A H20A . 0.9800 ?
    C20A H20B . 0.9800 ?
    C20A H20C . 0.9800 ?
    O1B C19B . 1.3536(17) ?
    O1B H1OB . 0.91(2) ?
    O2B C15B . 1.3648(17) ?
    O2B C20B . 1.4269(17) ?
    N1B C1B . 1.2915(18) ?
    N1B N2B . 1.4016(16) ?
    N2B C3B . 1.469(2) ?
    N2B H2NB . 0.911(19) ?
    C1B C14B . 1.4699(18) ?
    C1B C2B . 1.5121(18) ?
    C2B C3B . 1.5354(18) ?
    C2B H2BA . 0.9900 ?
    C2B H2BB . 0.9900 ?
    C3B C4B . 1.5155(18) ?
    C3B H3BA . 1.0000 ?
    C4B C13B . 1.3706(19) ?
    C4B C5B . 1.412(2) ?
    C5B C6B . 1.369(2) ?
    C5B H5BA . 0.9500 ?
    C6B C7B . 1.413(2) ?
    C6B H6BA . 0.9500 ?
    C7B C12B . 1.4216(19) ?
    C7B C8B . 1.4239(19) ?
    C8B C9B . 1.366(2) ?
    C8B H8BA . 0.9500 ?
    C9B C10B . 1.404(2) ?
    C9B H9BA . 0.9500 ?
    C10B C11B . 1.368(2) ?
    C10B H10B . 0.9500 ?
    C11B C12B . 1.4128(19) ?
    C11B H11B . 0.9500 ?
    C12B C13B . 1.4211(18) ?
    C13B H13B . 0.9500 ?
    C14B C15B . 1.4096(19) ?
    C14B C19B . 1.4159(19) ?
    C15B C16B . 1.3909(18) ?
    C16B C17B . 1.387(2) ?
    C16B H16B . 0.9500 ?
    C17B C18B . 1.372(2) ?
    C17B H17B . 0.9500 ?
    C18B C19B . 1.3936(19) ?
    C18B H18B . 0.9500 ?
    C20B H20D . 0.9800 ?
    C20B H20E . 0.9800 ?
    C20B H20F . 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
    C19A O1A H1OA . . 108.1(13) ?
    C15A O2A C20A . . 117.08(12) ?
    C1A N1A N2A . . 109.97(11) ?
    N1A N2A C3A . . 107.15(11) ?
    N1A N2A H2NA . . 106.4(11) ?
    C3A N2A H2NA . . 114.3(11) ?
    N1A C1A C14A . . 119.87(12) ?
    N1A C1A C2A . . 111.55(11) ?
    C14A C1A C2A . . 128.58(12) ?
    C1A C2A C3A . . 100.66(10) ?
    C1A C2A H2AA . . 111.6 ?
    C3A C2A H2AA . . 111.6 ?
    C1A C2A H2AB . . 111.6 ?
    C3A C2A H2AB . . 111.6 ?
    H2AA C2A H2AB . . 109.4 ?
    N2A C3A C4A . . 113.94(11) ?
    N2A C3A C2A . . 101.37(11) ?
    C4A C3A C2A . . 114.39(11) ?
    N2A C3A H3AA . . 108.9 ?
    C4A C3A H3AA . . 108.9 ?
    C2A C3A H3AA . . 108.9 ?
    C13A C4A C5A . . 118.88(12) ?
    C13A C4A C3A . . 122.98(12) ?
    C5A C4A C3A . . 118.12(12) ?
    C6A C5A C4A . . 121.26(13) ?
    C6A C5A H5AA . . 119.4 ?
    C4A C5A H5AA . . 119.4 ?
    C5A C6A C7A . . 120.92(13) ?
    C5A C6A H6AA . . 119.5 ?
    C7A C6A H6AA . . 119.5 ?
    C6A C7A C8A . . 122.70(13) ?
    C6A C7A C12A . . 118.45(12) ?
    C8A C7A C12A . . 118.83(13) ?
    C9A C8A C7A . . 120.96(13) ?
    C9A C8A H8AA . . 119.5 ?
    C7A C8A H8AA . . 119.5 ?
    C8A C9A C10A . . 120.46(13) ?
    C8A C9A H9AA . . 119.8 ?
    C10A C9A H9AA . . 119.8 ?
    C11A C10A C9A . . 120.27(14) ?
    C11A C10A H10A . . 119.9 ?
    C9A C10A H10A . . 119.9 ?
    C10A C11A C12A . . 120.87(13) ?
    C10A C11A H11A . . 119.6 ?
    C12A C11A H11A . . 119.6 ?
    C11A C12A C13A . . 122.43(12) ?
    C11A C12A C7A . . 118.60(12) ?
    C13A C12A C7A . . 118.97(12) ?
    C4A C13A C12A . . 121.50(12) ?
    C4A C13A H13A . . 119.2 ?
    C12A C13A H13A . . 119.2 ?
    C19A C14A C15A . . 117.46(13) ?
    C19A C14A C1A . . 120.57(12) ?
    C15A C14A C1A . . 121.95(12) ?
    O2A C15A C16A . . 123.43(13) ?
    O2A C15A C14A . . 115.27(12) ?
    C16A C15A C14A . . 121.28(14) ?
    C17A C16A C15A . . 119.08(15) ?
    C17A C16A H16A . . 120.5 ?
    C15A C16A H16A . . 120.5 ?
    C18A C17A C16A . . 121.53(14) ?
    C18A C17A H17A . . 119.2 ?
    C16A C17A H17A . . 119.2 ?
    C17A C18A C19A . . 119.57(14) ?
    C17A C18A H18A . . 120.2 ?
    C19A C18A H18A . . 120.2 ?
    O1A C19A C18A . . 117.18(13) ?
    O1A C19A C14A . . 121.87(13) ?
    C18A C19A C14A . . 120.94(14) ?
    O2A C20A H20A . . 109.5 ?
    O2A C20A H20B . . 109.5 ?
    H20A C20A H20B . . 109.5 ?
    O2A C20A H20C . . 109.5 ?
    H20A C20A H20C . . 109.5 ?
    H20B C20A H20C . . 109.5 ?
    C19B O1B H1OB . . 107.5(14) ?
    C15B O2B C20B . . 117.68(10) ?
    C1B N1B N2B . . 110.08(11) ?
    N1B N2B C3B . . 107.86(11) ?
    N1B N2B H2NB . . 108.9(11) ?
    C3B N2B H2NB . . 114.9(12) ?
    N1B C1B C14B . . 119.81(12) ?
    N1B C1B C2B . . 111.08(11) ?
    C14B C1B C2B . . 129.05(11) ?
    C1B C2B C3B . . 101.06(10) ?
    C1B C2B H2BA . . 111.6 ?
    C3B C2B H2BA . . 111.6 ?
    C1B C2B H2BB . . 111.6 ?
    C3B C2B H2BB . . 111.6 ?
    H2BA C2B H2BB . . 109.4 ?
    N2B C3B C4B . . 111.84(11) ?
    N2B C3B C2B . . 101.06(11) ?
    C4B C3B C2B . . 115.47(11) ?
    N2B C3B H3BA . . 109.4 ?
    C4B C3B H3BA . . 109.4 ?
    C2B C3B H3BA . . 109.4 ?
    C13B C4B C5B . . 119.33(12) ?
    C13B C4B C3B . . 121.31(12) ?
    C5B C4B C3B . . 119.36(12) ?
    C6B C5B C4B . . 120.80(13) ?
    C6B C5B H5BA . . 119.6 ?
    C4B C5B H5BA . . 119.6 ?
    C5B C6B C7B . . 121.10(13) ?
    C5B C6B H6BA . . 119.5 ?
    C7B C6B H6BA . . 119.5 ?
    C6B C7B C12B . . 118.54(12) ?
    C6B C7B C8B . . 122.99(13) ?
    C12B C7B C8B . . 118.46(13) ?
    C9B C8B C7B . . 120.95(14) ?
    C9B C8B H8BA . . 119.5 ?
    C7B C8B H8BA . . 119.5 ?
    C8B C9B C10B . . 120.43(13) ?
    C8B C9B H9BA . . 119.8 ?
    C10B C9B H9BA . . 119.8 ?
    C11B C10B C9B . . 120.01(14) ?
    C11B C10B H10B . . 120.0 ?
    C9B C10B H10B . . 120.0 ?
    C10B C11B C12B . . 121.32(13) ?
    C10B C11B H11B . . 119.3 ?
    C12B C11B H11B . . 119.3 ?
    C11B C12B C13B . . 122.25(12) ?
    C11B C12B C7B . . 118.81(12) ?
    C13B C12B C7B . . 118.94(12) ?
    C4B C13B C12B . . 121.28(12) ?
    C4B C13B H13B . . 119.4 ?
    C12B C13B H13B . . 119.4 ?
    C15B C14B C19B . . 117.35(12) ?
    C15B C14B C1B . . 122.59(12) ?
    C19B C14B C1B . . 120.05(12) ?
    O2B C15B C16B . . 123.04(12) ?
    O2B C15B C14B . . 115.96(11) ?
    C16B C15B C14B . . 120.99(13) ?
    C17B C16B C15B . . 119.57(13) ?
    C17B C16B H16B . . 120.2 ?
    C15B C16B H16B . . 120.2 ?
    C18B C17B C16B . . 121.40(13) ?
    C18B C17B H17B . . 119.3 ?
    C16B C17B H17B . . 119.3 ?
    C17B C18B C19B . . 119.32(14) ?
    C17B C18B H18B . . 120.3 ?
    C19B C18B H18B . . 120.3 ?
    O1B C19B C18B . . 117.24(12) ?
    O1B C19B C14B . . 121.46(12) ?
    C18B C19B C14B . . 121.30(13) ?
    O2B C20B H20D . . 109.5 ?
    O2B C20B H20E . . 109.5 ?
    H20D C20B H20E . . 109.5 ?
    O2B C20B H20F . . 109.5 ?
    H20D C20B H20F . . 109.5 ?
    H20E C20B H20F . . 109.5 ?
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
    O1A H1OA N1A . 0.97(2) 1.71(2) 2.5754(15) 145(2)
    O1B H1OB N1B . 0.91(2) 1.71(2) 2.5377(15) 149(2)
    N2A H2NA O1A 3_666 0.914(18) 2.234(18) 3.0470(16) 147.7(15)
    N2B H2NB O1B 3_536 0.911(19) 2.131(19) 2.9787(16) 154.4(15)
