##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     'APEX2 v2013.2-RC1'
_journal_date_recd_electronic     2013-08-27
_journal_date_accepted     2013-10-11
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue     11
_journal_page_first     o1680
_journal_page_last     o1681
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681302802X
_journal_coeditor_code     QK2060
_publ_contact_author_name     'Nicholas R. Natale'
_publ_contact_author_address
;
The University of Montana-Missoula
The Department of Biomedical & Pharmaceutical Sciences
Missoula
MT 59812-1552
USA
;
_publ_contact_author_email     nicholas.natale@umontana.edu
_publ_contact_author_fax     '(406) 243-4132'
_publ_contact_author_phone     '(406) 243-4132'
_publ_section_title
;\
3-(1,3-Diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-<i>d</i>]pyridazin-\
7(6<i>H</i>)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Campana, Charles F.' .
;
Bruker AXS Inc.
5465 East Cheryl Parkway
Madison, WI 53711
USA
;
    'Mirzaei, Joseph' .
;
The University of Montana-Missoula
The Department of Biomedical & Pharmaceutical Sciences
Missoula, MT 59812-1552
USA
;
    'Koerner, Chris' .
;
The University of Montana-Missoula
The Department of Biomedical & Pharmaceutical Sciences
Missoula, MT 59812-1552
USA
;
    'Gates, Christina' .
;
The University of Montana-Missoula
The Department of Biomedical & Pharmaceutical Sciences
Missoula, MT 59812-1552
USA
;
    'Natale, Nicholas R.' .
;
The University of Montana-Missoula
The Department of Biomedical & Pharmaceutical Sciences
Missoula, MT 59812-1552
USA
;
_publ_section_synopsis     .
data_I
_database_code_depnum_ccdc_archive     'CCDC 966122'
_chemical_name_systematic
;\
3-(1,3-Diphenylpropan-2-yl)-4-methyl-6-phenylisoxazolo[3,4-<i>d</i>]pyridazin-\
7(6<i>H</i>)-one
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C27 H23 N3 O2'
_chemical_formula_sum     'C27 H23 N3 O2'
_chemical_formula_iupac     'C27 H23 N3 O2'
_chemical_formula_weight     421.48
_chemical_melting_point     ?
_symmetry_space_group_name_hall     '-P 1'
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.5163(4)
_cell_length_b     9.6774(5)
_cell_length_c     15.9053(8)
_cell_angle_alpha     86.7980(10)
_cell_angle_beta     83.5120(10)
_cell_angle_gamma     69.3850(10)
_cell_volume     1075.75(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9923
_cell_measurement_theta_min     2.7965
_cell_measurement_theta_max     68.3456
_cell_measurement_temperature     100.(2)
_cell_special_details     'calculated from global refinement'
_exptl_crystal_description     prism
_exptl_crystal_colour     'clear light yellow'
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.220
_exptl_crystal_size_min     0.190
_exptl_crystal_density_diffrn     1.301
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     444
_exptl_absorpt_coefficient_mu     0.664
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS; Bruker, 2012)'
_exptl_absorpt_correction_T_min     0.80
_exptl_absorpt_correction_T_max     0.89
_exptl_special_details
;
;
_diffrn_ambient_temperature     100.(2)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Cu K\a'
_diffrn_radiation_monochromator     mirrors
_diffrn_measurement_device_type     'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method     'omega and phi scans'
_diffrn_detector_area_resol_mean     10.4167
_diffrn_reflns_number     12012
_diffrn_reflns_av_R_equivalents     0.0165
_diffrn_reflns_av_sigmaI/netI     0.0189
_diffrn_reflns_theta_min     2.80
_diffrn_reflns_theta_max     66.59
_diffrn_reflns_theta_full     66.59
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     3
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3714
_reflns_number_gt     3597
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0323
_refine_ls_R_factor_gt     0.0315
_refine_ls_wR_factor_gt     0.0774
_refine_ls_wR_factor_ref     0.0781
_refine_ls_goodness_of_fit_ref     1.028
_refine_ls_restrained_S_all     1.016
_refine_ls_number_reflns     3714
_refine_ls_number_parameters     313
_refine_ls_number_restraints     86
_refine_ls_number_constraints     0
_refine_ls_hydrogen_treatment     refU
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+0.3370P] where P=(Fo^2^+2Fc^2^)/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     0.217
_refine_diff_density_min     -0.140
_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     'SMART (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     'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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 0.00502(11) 0.47448(8) 0.64153(5) 0.02756(18) Uani d U 1 . .
    N N1 0.15001(13) 0.33590(10) 0.65000(6) 0.0270(2) Uani d U 1 . .
    C C1 0.25346(14) 0.36020(11) 0.70485(6) 0.0222(2) Uani d U 1 . .
    C C2 0.42780(15) 0.24940(11) 0.73381(6) 0.0226(2) Uani d U 1 . .
    O O2 0.49243(11) 0.11970(8) 0.71482(5) 0.02828(18) Uani d U 1 . .
    N N2 0.51293(12) 0.31237(9) 0.78613(5) 0.02217(19) Uani d U 1 . .
    N N3 0.44085(12) 0.45480(9) 0.81882(5) 0.0235(2) Uani d U 1 . .
    C C3 0.28457(14) 0.54911(11) 0.79389(6) 0.0224(2) Uani d U 1 . .
    C C4 0.18507(14) 0.50724(11) 0.73305(6) 0.0217(2) Uani d U 1 . .
    C C5 0.02762(15) 0.57547(12) 0.69057(6) 0.0232(2) Uani d U 1 . .
    C C6 0.69832(14) 0.22965(11) 0.81342(7) 0.0224(2) Uani d U 1 . .
    C C7 0.85159(15) 0.16976(11) 0.75336(7) 0.0260(2) Uani d U 1 . .
    H H7 0.8334 0.1771 0.6949 0.030(3) Uiso calc R 1 . .
    C C8 1.03243(15) 0.09880(12) 0.77969(7) 0.0278(2) Uani d U 1 . .
    H H8 1.1385 0.0572 0.739 0.034(3) Uiso calc R 1 . .
    C C9 1.05866(16) 0.08840(12) 0.86484(7) 0.0284(2) Uani d U 1 . .
    H H9 1.1823 0.0391 0.8826 0.033(3) Uiso calc R 1 . .
    C C10 0.90441(16) 0.15001(12) 0.92425(7) 0.0273(2) Uani d U 1 . .
    H H10 0.9229 0.1434 0.9827 0.032(3) Uiso calc R 1 . .
    C C11 0.72289(15) 0.22140(11) 0.89891(7) 0.0248(2) Uani d U 1 . .
    H H11 0.6171 0.264 0.9396 0.025(3) Uiso calc R 1 . .
    C C12 0.21729(16) 0.69938(12) 0.83066(8) 0.0295(2) Uani d U 1 . .
    H H12A 0.3036 0.7028 0.8717 0.039(4) Uiso calc R 1 . .
    H H12B 0.0879 0.7216 0.8591 0.039(4) Uiso calc R 1 . .
    H H12C 0.2161 0.7725 0.7854 0.043(4) Uiso calc R 1 . .
    C C13 -0.11611(15) 0.72853(12) 0.68583(7) 0.0255(2) Uani d U 1 . .
    H H13 -0.0688 0.7945 0.7162 0.019(3) Uiso calc R 1 . .
    C C14 -0.31156(15) 0.73629(12) 0.73267(7) 0.0279(2) Uani d U 1 . .
    H H14A -0.4109 0.831 0.7186 0.032(3) Uiso calc R 1 . .
    H H14B -0.3481 0.6549 0.7141 0.029(3) Uiso calc R 1 . .
    C C15 -0.29925(14) 0.72404(12) 0.82684(7) 0.0256(2) Uani d U 1 . .
    C C16 -0.24282(15) 0.58718(12) 0.86891(7) 0.0280(2) Uani d U 1 . .
    H H16 -0.222 0.5 0.8387 0.028(3) Uiso calc R 1 . .
    C C17 -0.21682(16) 0.57717(13) 0.95421(7) 0.0306(3) Uani d U 1 . .
    H H17 -0.1802 0.4835 0.9822 0.038(4) Uiso calc R 1 . .
    C C18 -0.24399(15) 0.70303(13) 0.99886(7) 0.0302(3) Uani d U 1 . .
    H H18 -0.2237 0.6958 1.0571 0.034(3) Uiso calc R 1 . .
    C C19 -0.30114(15) 0.83994(13) 0.95784(7) 0.0296(2) Uani d U 1 . .
    H H19 -0.3209 0.9268 0.9882 0.032(3) Uiso calc R 1 . .
    C C20 -0.32932(15) 0.85002(12) 0.87290(7) 0.0278(2) Uani d U 1 . .
    H H20 -0.3697 0.9442 0.8456 0.034(3) Uiso calc R 1 . .
    C C21 -0.12730(16) 0.78383(13) 0.59301(7) 0.0302(3) Uani d U 1 . .
    H H21A -0.1683 0.7183 0.5602 0.029(3) Uiso calc R 1 . .
    H H21B -0.2235 0.8846 0.5907 0.038(4) Uiso calc R 1 . .
    C C22 0.13242(17) 0.89367(13) 0.57720(7) 0.0308(3) Uani d U 1 . .
    H H22 0.0532 0.9691 0.6146 0.037(4) Uiso calc R 1 . .
    C C23 0.31273(18) 0.89326(13) 0.54685(7) 0.0336(3) Uani d U 1 . .
    H H23 0.357 0.9668 0.5641 0.039(4) Uiso calc R 1 . .
    C C24 0.42832(17) 0.78538(14) 0.49126(7) 0.0343(3) Uani d U 1 . .
    H H24 0.5519 0.7848 0.47 0.039(4) Uiso calc R 1 . .
    C C25 0.36233(18) 0.67858(14) 0.46702(7) 0.0355(3) Uani d U 1 . .
    H H25 0.4407 0.6048 0.4285 0.046(4) Uiso calc R 1 . .
    C C26 0.18236(18) 0.67824(13) 0.49847(7) 0.0322(3) Uani d U 1 . .
    H H26 0.1394 0.6036 0.4817 0.036(3) Uiso calc R 1 . .
    C C27 0.06465(16) 0.78583(12) 0.55409(7) 0.0271(2) Uani d U 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0275(4) 0.0247(4) 0.0302(4) -0.0066(3) -0.0104(3) 0.0004(3)
    N1 0.0273(5) 0.0231(5) 0.0295(5) -0.0062(4) -0.0071(4) 0.0001(4)
    C1 0.0238(5) 0.0218(5) 0.0219(5) -0.0093(4) -0.0024(4) 0.0019(4)
    C2 0.0245(5) 0.0203(5) 0.0230(5) -0.0085(4) -0.0019(4) 0.0013(4)
    O2 0.0309(4) 0.0197(4) 0.0334(4) -0.0068(3) -0.0064(3) -0.0008(3)
    N2 0.0219(4) 0.0175(4) 0.0257(4) -0.0045(3) -0.0044(3) 0.0001(3)
    N3 0.0227(4) 0.0194(4) 0.0273(5) -0.0057(3) -0.0033(3) -0.0016(3)
    C3 0.0203(5) 0.0218(5) 0.0249(5) -0.0074(4) -0.0030(4) 0.0017(4)
    C4 0.0218(5) 0.0200(5) 0.0229(5) -0.0075(4) -0.0013(4) 0.0021(4)
    C5 0.0232(5) 0.0241(5) 0.0236(5) -0.0094(4) -0.0042(4) 0.0017(4)
    C6 0.0216(5) 0.0163(5) 0.0296(5) -0.0063(4) -0.0059(4) 0.0031(4)
    C7 0.0282(6) 0.0219(5) 0.0261(5) -0.0065(4) -0.0039(4) 0.0013(4)
    C8 0.0244(5) 0.0222(5) 0.0336(6) -0.0045(4) -0.0011(4) -0.0012(4)
    C9 0.0241(5) 0.0215(5) 0.0383(6) -0.0049(4) -0.0097(4) 0.0030(4)
    C10 0.0300(6) 0.0238(5) 0.0283(6) -0.0083(4) -0.0089(4) 0.0037(4)
    C11 0.0249(5) 0.0219(5) 0.0273(5) -0.0081(4) -0.0027(4) 0.0013(4)
    C12 0.0243(5) 0.0244(6) 0.0389(6) -0.0051(4) -0.0086(5) -0.0052(5)
    C13 0.0237(5) 0.0230(5) 0.0295(6) -0.0065(4) -0.0082(4) 0.0033(4)
    C14 0.0224(5) 0.0244(6) 0.0363(6) -0.0064(4) -0.0080(4) 0.0026(4)
    C15 0.0171(5) 0.0251(5) 0.0349(6) -0.0078(4) -0.0035(4) 0.0023(4)
    C16 0.0235(5) 0.0232(5) 0.0387(6) -0.0097(4) -0.0046(4) 0.0010(5)
    C17 0.0270(6) 0.0267(6) 0.0391(6) -0.0116(4) -0.0044(5) 0.0081(5)
    C18 0.0246(5) 0.0354(6) 0.0303(6) -0.0111(5) -0.0002(4) 0.0022(5)
    C19 0.0230(5) 0.0274(6) 0.0365(6) -0.0072(4) 0.0013(4) -0.0040(5)
    C20 0.0210(5) 0.0214(5) 0.0384(6) -0.0050(4) -0.0018(4) 0.0033(4)
    C21 0.0293(6) 0.0295(6) 0.0318(6) -0.0084(5) -0.0124(5) 0.0076(5)
    C22 0.0362(6) 0.0266(6) 0.0277(6) -0.0081(5) -0.0059(5) 0.0013(4)
    C23 0.0416(7) 0.0345(6) 0.0302(6) -0.0188(5) -0.0100(5) 0.0050(5)
    C24 0.0332(6) 0.0421(7) 0.0279(6) -0.0138(5) -0.0056(5) 0.0075(5)
    C25 0.0425(7) 0.0348(7) 0.0256(6) -0.0099(5) -0.0003(5) -0.0002(5)
    C26 0.0437(7) 0.0307(6) 0.0251(5) -0.0153(5) -0.0088(5) 0.0018(4)
    C27 0.0304(6) 0.0271(6) 0.0235(5) -0.0081(4) -0.0116(4) 0.0078(4)
_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
    O1 C5 . 1.3506(13) ?
    O1 N1 . 1.4100(11) ?
    N1 C1 . 1.3138(14) ?
    C1 C4 . 1.4122(14) ?
    C1 C2 . 1.4734(14) ?
    C2 O2 . 1.2176(13) ?
    C2 N2 . 1.3873(13) ?
    N2 N3 . 1.3979(12) ?
    N2 C6 . 1.4434(13) ?
    N3 C3 . 1.2961(13) ?
    C3 C4 . 1.4425(15) ?
    C3 C12 . 1.4909(15) ?
    C4 C5 . 1.3688(15) ?
    C5 C13 . 1.4986(14) ?
    C6 C7 . 1.3851(15) ?
    C6 C11 . 1.3869(15) ?
    C7 C8 . 1.3906(16) ?
    C7 H7 . 0.95 ?
    C8 C9 . 1.3835(16) ?
    C8 H8 . 0.95 ?
    C9 C10 . 1.3861(16) ?
    C9 H9 . 0.95 ?
    C10 C11 . 1.3895(15) ?
    C10 H10 . 0.95 ?
    C11 H11 . 0.95 ?
    C12 H12A . 0.98 ?
    C12 H12B . 0.98 ?
    C12 H12C . 0.98 ?
    C13 C21 . 1.5431(15) ?
    C13 C14 . 1.5492(15) ?
    C13 H13 . 1.0 ?
    C14 C15 . 1.5067(16) ?
    C14 H14A . 0.99 ?
    C14 H14B . 0.99 ?
    C15 C20 . 1.3937(16) ?
    C15 C16 . 1.3968(15) ?
    C16 C17 . 1.3857(17) ?
    C16 H16 . 0.95 ?
    C17 C18 . 1.3851(17) ?
    C17 H17 . 0.95 ?
    C18 C19 . 1.3898(16) ?
    C18 H18 . 0.95 ?
    C19 C20 . 1.3839(17) ?
    C19 H19 . 0.95 ?
    C20 H20 . 0.95 ?
    C21 C27 . 1.5105(16) ?
    C21 H21A . 0.99 ?
    C21 H21B . 0.99 ?
    C22 C23 . 1.3850(17) ?
    C22 C27 . 1.3940(16) ?
    C22 H22 . 0.95 ?
    C23 C24 . 1.3847(18) ?
    C23 H23 . 0.95 ?
    C24 C25 . 1.3825(18) ?
    C24 H24 . 0.95 ?
    C25 C26 . 1.3893(18) ?
    C25 H25 . 0.95 ?
    C26 C27 . 1.3881(16) ?
    C26 H26 . 0.95 ?
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
    C5 O1 N1 . . 110.86(8) ?
    C1 N1 O1 . . 103.37(8) ?
    N1 C1 C4 . . 113.41(9) ?
    N1 C1 C2 . . 124.88(9) ?
    C4 C1 C2 . . 121.68(9) ?
    O2 C2 N2 . . 123.36(9) ?
    O2 C2 C1 . . 125.71(10) ?
    N2 C2 C1 . . 110.93(9) ?
    C2 N2 N3 . . 127.80(8) ?
    C2 N2 C6 . . 120.74(8) ?
    N3 N2 C6 . . 111.46(8) ?
    C3 N3 N2 . . 119.61(9) ?
    N3 C3 C4 . . 120.23(9) ?
    N3 C3 C12 . . 116.70(9) ?
    C4 C3 C12 . . 123.07(9) ?
    C5 C4 C1 . . 104.21(9) ?
    C5 C4 C3 . . 136.51(10) ?
    C1 C4 C3 . . 119.28(9) ?
    O1 C5 C4 . . 108.15(9) ?
    O1 C5 C13 . . 115.96(9) ?
    C4 C5 C13 . . 135.89(10) ?
    C7 C6 C11 . . 121.11(10) ?
    C7 C6 N2 . . 119.36(9) ?
    C11 C6 N2 . . 119.33(9) ?
    C6 C7 C8 . . 119.17(10) ?
    C6 C7 H7 . . 120.4 ?
    C8 C7 H7 . . 120.4 ?
    C9 C8 C7 . . 120.33(10) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8 C9 C10 . . 119.94(10) ?
    C8 C9 H9 . . 120.0 ?
    C10 C9 H9 . . 120.0 ?
    C9 C10 C11 . . 120.40(10) ?
    C9 C10 H10 . . 119.8 ?
    C11 C10 H10 . . 119.8 ?
    C6 C11 C10 . . 119.05(10) ?
    C6 C11 H11 . . 120.5 ?
    C10 C11 H11 . . 120.5 ?
    C3 C12 H12A . . 109.5 ?
    C3 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    C3 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C5 C13 C21 . . 110.34(9) ?
    C5 C13 C14 . . 110.96(9) ?
    C21 C13 C14 . . 113.70(9) ?
    C5 C13 H13 . . 107.2 ?
    C21 C13 H13 . . 107.2 ?
    C14 C13 H13 . . 107.2 ?
    C15 C14 C13 . . 109.92(8) ?
    C15 C14 H14A . . 109.7 ?
    C13 C14 H14A . . 109.7 ?
    C15 C14 H14B . . 109.7 ?
    C13 C14 H14B . . 109.7 ?
    H14A C14 H14B . . 108.2 ?
    C20 C15 C16 . . 118.33(10) ?
    C20 C15 C14 . . 119.92(10) ?
    C16 C15 C14 . . 121.55(10) ?
    C17 C16 C15 . . 120.73(10) ?
    C17 C16 H16 . . 119.6 ?
    C15 C16 H16 . . 119.6 ?
    C18 C17 C16 . . 120.33(10) ?
    C18 C17 H17 . . 119.8 ?
    C16 C17 H17 . . 119.8 ?
    C17 C18 C19 . . 119.48(11) ?
    C17 C18 H18 . . 120.3 ?
    C19 C18 H18 . . 120.3 ?
    C20 C19 C18 . . 120.14(11) ?
    C20 C19 H19 . . 119.9 ?
    C18 C19 H19 . . 119.9 ?
    C19 C20 C15 . . 120.97(10) ?
    C19 C20 H20 . . 119.5 ?
    C15 C20 H20 . . 119.5 ?
    C27 C21 C13 . . 110.58(9) ?
    C27 C21 H21A . . 109.5 ?
    C13 C21 H21A . . 109.5 ?
    C27 C21 H21B . . 109.5 ?
    C13 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 108.1 ?
    C23 C22 C27 . . 121.42(11) ?
    C23 C22 H22 . . 119.3 ?
    C27 C22 H22 . . 119.3 ?
    C24 C23 C22 . . 119.85(11) ?
    C24 C23 H23 . . 120.1 ?
    C22 C23 H23 . . 120.1 ?
    C25 C24 C23 . . 119.42(11) ?
    C25 C24 H24 . . 120.3 ?
    C23 C24 H24 . . 120.3 ?
    C24 C25 C26 . . 120.56(11) ?
    C24 C25 H25 . . 119.7 ?
    C26 C25 H25 . . 119.7 ?
    C27 C26 C25 . . 120.70(11) ?
    C27 C26 H26 . . 119.6 ?
    C25 C26 H26 . . 119.6 ?
    C26 C27 C22 . . 118.05(11) ?
    C26 C27 C21 . . 121.96(10) ?
    C22 C27 C21 . . 119.91(10) ?
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
    C5 O1 N1 C1 . . . . 0.42(11) ?
    O1 N1 C1 C4 . . . . -0.08(11) ?
    O1 N1 C1 C2 . . . . -178.31(9) ?
    N1 C1 C2 O2 . . . . -4.53(17) ?
    C4 C1 C2 O2 . . . . 177.38(10) ?
    N1 C1 C2 N2 . . . . 174.91(10) ?
    C4 C1 C2 N2 . . . . -3.18(13) ?
    O2 C2 N2 N3 . . . . -172.66(9) ?
    C1 C2 N2 N3 . . . . 7.88(14) ?
    O2 C2 N2 C6 . . . . 7.42(15) ?
    C1 C2 N2 C6 . . . . -172.03(8) ?
    C2 N2 N3 C3 . . . . -6.84(15) ?
    C6 N2 N3 C3 . . . . 173.09(9) ?
    N2 N3 C3 C4 . . . . 0.28(14) ?
    N2 N3 C3 C12 . . . . -179.32(9) ?
    N1 C1 C4 C5 . . . . -0.26(12) ?
    C2 C1 C4 C5 . . . . 178.03(9) ?
    N1 C1 C4 C3 . . . . 179.63(9) ?
    C2 C1 C4 C3 . . . . -2.08(15) ?
    N3 C3 C4 C5 . . . . -176.42(11) ?
    C12 C3 C4 C5 . . . . 3.15(19) ?
    N3 C3 C4 C1 . . . . 3.73(15) ?
    C12 C3 C4 C1 . . . . -176.70(10) ?
    N1 O1 C5 C4 . . . . -0.60(11) ?
    N1 O1 C5 C13 . . . . 178.88(8) ?
    C1 C4 C5 O1 . . . . 0.51(11) ?
    C3 C4 C5 O1 . . . . -179.35(11) ?
    C1 C4 C5 C13 . . . . -178.82(11) ?
    C3 C4 C5 C13 . . . . 1.3(2) ?
    C2 N2 C6 C7 . . . . 56.43(13) ?
    N3 N2 C6 C7 . . . . -123.50(10) ?
    C2 N2 C6 C11 . . . . -128.58(10) ?
    N3 N2 C6 C11 . . . . 51.49(12) ?
    C11 C6 C7 C8 . . . . 0.76(16) ?
    N2 C6 C7 C8 . . . . 175.67(9) ?
    C6 C7 C8 C9 . . . . -0.07(16) ?
    C7 C8 C9 C10 . . . . -0.54(16) ?
    C8 C9 C10 C11 . . . . 0.47(16) ?
    C7 C6 C11 C10 . . . . -0.83(16) ?
    N2 C6 C11 C10 . . . . -175.73(9) ?
    C9 C10 C11 C6 . . . . 0.20(16) ?
    O1 C5 C13 C21 . . . . -53.31(12) ?
    C4 C5 C13 C21 . . . . 125.98(13) ?
    O1 C5 C13 C14 . . . . 73.63(11) ?
    C4 C5 C13 C14 . . . . -107.07(14) ?
    C5 C13 C14 C15 . . . . 71.49(11) ?
    C21 C13 C14 C15 . . . . -163.44(9) ?
    C13 C14 C15 C20 . . . . 86.05(12) ?
    C13 C14 C15 C16 . . . . -88.63(12) ?
    C20 C15 C16 C17 . . . . -0.22(15) ?
    C14 C15 C16 C17 . . . . 174.54(10) ?
    C15 C16 C17 C18 . . . . -0.90(16) ?
    C16 C17 C18 C19 . . . . 1.23(16) ?
    C17 C18 C19 C20 . . . . -0.44(16) ?
    C18 C19 C20 C15 . . . . -0.69(16) ?
    C16 C15 C20 C19 . . . . 1.01(15) ?
    C14 C15 C20 C19 . . . . -173.84(10) ?
    C5 C13 C21 C27 . . . . -59.69(12) ?
    C14 C13 C21 C27 . . . . 174.90(9) ?
    C27 C22 C23 C24 . . . . 1.06(17) ?
    C22 C23 C24 C25 . . . . -0.34(17) ?
    C23 C24 C25 C26 . . . . -0.50(17) ?
    C24 C25 C26 C27 . . . . 0.65(17) ?
    C25 C26 C27 C22 . . . . 0.05(16) ?
    C25 C26 C27 C21 . . . . -176.67(10) ?
    C23 C22 C27 C26 . . . . -0.90(16) ?
    C23 C22 C27 C21 . . . . 175.88(10) ?
    C13 C21 C27 C26 . . . . 103.38(12) ?
    C13 C21 C27 C22 . . . . -73.27(12) ?
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
    C26 H26 O1 2_566 0.95 2.61 3.4159(13) 142.8
    C24 H24 N1 2_666 0.95 2.73 3.5407(15) 143.4
    C11 H11 C18 2_567 0.95 2.78 3.6182(15) 148.1
_iucr_refine_instructions_details
;
TITL Montana01 in P-1
CELL 1.54178   7.5163   9.6774  15.9053  86.798  83.512  69.385
ZERR    2.00   0.0004   0.0005   0.0008   0.001   0.001   0.001
LATT 1
SFAC C  H  N  O
UNIT 54  46  6  4
L.S. 10
SHEL 999 0.84
ACTA
BOND $H
FMAP 2
PLAN -5
SIZE 0.188 0.22 0.397
CONF
DELU
TEMP -173.000
WGHT    0.035200    0.337000
FVAR       0.28839
O1    4    0.005019    0.474482    0.641534    11.00000    0.02754    0.02469 =
         0.03018    0.00043   -0.01041   -0.00664
N1    3    0.150006    0.335904    0.649998    11.00000    0.02726    0.02305 =
         0.02948    0.00013   -0.00706   -0.00619
C1    1    0.253459    0.360201    0.704853    11.00000    0.02383    0.02182 =
         0.02190    0.00192   -0.00242   -0.00931
C2    1    0.427798    0.249396    0.733813    11.00000    0.02452    0.02032 =
         0.02302    0.00128   -0.00187   -0.00846
O2    4    0.492427    0.119696    0.714817    11.00000    0.03090    0.01967 =
         0.03344   -0.00080   -0.00636   -0.00680
N2    3    0.512927    0.312371    0.786128    11.00000    0.02187    0.01748 =
         0.02569    0.00007   -0.00440   -0.00450
N3    3    0.440849    0.454796    0.818824    11.00000    0.02268    0.01939 =
         0.02734   -0.00155   -0.00327   -0.00574
C3    1    0.284573    0.549111    0.793890    11.00000    0.02028    0.02184 =
         0.02494    0.00166   -0.00303   -0.00736
C4    1    0.185070    0.507239    0.733049    11.00000    0.02177    0.02005 =
         0.02290    0.00213   -0.00134   -0.00751
C5    1    0.027621    0.575467    0.690567    11.00000    0.02317    0.02409 =
         0.02359    0.00165   -0.00420   -0.00942
C6    1    0.698321    0.229645    0.813420    11.00000    0.02157    0.01628 =
         0.02964    0.00311   -0.00594   -0.00627
C7    1    0.851588    0.169761    0.753361    11.00000    0.02816    0.02188 =
         0.02613    0.00131   -0.00387   -0.00652
AFIX  43
H7    2    0.833397    0.177077    0.694912    11.00000    0.02991
AFIX   0
C8    1    1.032427    0.098796    0.779694    11.00000    0.02436    0.02215 =
         0.03364   -0.00119   -0.00113   -0.00449
AFIX  43
H8    2    1.138481    0.057249    0.739017    11.00000    0.03444
AFIX   0
C9    1    1.058662    0.088399    0.864840    11.00000    0.02408    0.02147 =
         0.03833    0.00303   -0.00974   -0.00490
AFIX  43
H9    2    1.182278    0.039076    0.882567    11.00000    0.03316
AFIX   0
C10   1    0.904415    0.150014    0.924253    11.00000    0.02998    0.02384 =
         0.02826    0.00375   -0.00890   -0.00828
AFIX  43
H10   2    0.922915    0.143395    0.982653    11.00000    0.03156
AFIX   0
C11   1    0.722886    0.221404    0.898910    11.00000    0.02493    0.02195 =
         0.02734    0.00131   -0.00270   -0.00809
AFIX  43
H11   2    0.617128    0.263955    0.939556    11.00000    0.02532
AFIX   0
C12   1    0.217287    0.699378    0.830655    11.00000    0.02431    0.02439 =
         0.03891   -0.00518   -0.00864   -0.00511
AFIX 137
H12A  2    0.303562    0.702756    0.871685    11.00000    0.03938
H12B  2    0.087929    0.721637    0.859096    11.00000    0.03858
H12C  2    0.216142    0.772516    0.785351    11.00000    0.04306
AFIX   0
C13   1   -0.116106    0.728529    0.685832    11.00000    0.02366    0.02304 =
         0.02946    0.00332   -0.00823   -0.00648
AFIX  13
H13   2   -0.068761    0.794453    0.716196    11.00000    0.01905
AFIX   0
C14   1   -0.311556    0.736291    0.732666    11.00000    0.02241    0.02440 =
         0.03632    0.00257   -0.00803   -0.00638
AFIX  23
H14A  2   -0.410860    0.830983    0.718601    11.00000    0.03191
H14B  2   -0.348112    0.654890    0.714090    11.00000    0.02861
AFIX   0
C15   1   -0.299252    0.724037    0.826845    11.00000    0.01712    0.02508 =
         0.03490    0.00232   -0.00348   -0.00776
C16   1   -0.242816    0.587179    0.868908    11.00000    0.02347    0.02317 =
         0.03875    0.00100   -0.00464   -0.00969
AFIX  43
H16   2   -0.222023    0.500000    0.838700    11.00000    0.02807
AFIX   0
C17   1   -0.216823    0.577166    0.954210    11.00000    0.02702    0.02671 =
         0.03915    0.00808   -0.00436   -0.01162
AFIX  43
H17   2   -0.180185    0.483505    0.982204    11.00000    0.03792
AFIX   0
C18   1   -0.243993    0.703031    0.998863    11.00000    0.02460    0.03535 =
         0.03035    0.00220   -0.00024   -0.01113
AFIX  43
H18   2   -0.223722    0.695833    1.057074    11.00000    0.03387
AFIX   0
C19   1   -0.301143    0.839940    0.957843    11.00000    0.02297    0.02738 =
         0.03651   -0.00396    0.00128   -0.00721
AFIX  43
H19   2   -0.320911    0.926789    0.988182    11.00000    0.03223
AFIX   0
C20   1   -0.329317    0.850024    0.872896    11.00000    0.02104    0.02141 =
         0.03838    0.00329   -0.00184   -0.00495
AFIX  43
H20   2   -0.369744    0.944207    0.845572    11.00000    0.03428
AFIX   0
C21   1   -0.127301    0.783825    0.593010    11.00000    0.02927    0.02947 =
         0.03180    0.00764   -0.01242   -0.00840
AFIX  23
H21A  2   -0.168272    0.718296    0.560202    11.00000    0.02858
H21B  2   -0.223452    0.884579    0.590718    11.00000    0.03841
AFIX   0
C22   1    0.132419    0.893672    0.577195    11.00000    0.03616    0.02656 =
         0.02773    0.00127   -0.00586   -0.00810
AFIX  43
H22   2    0.053227    0.969069    0.614558    11.00000    0.03718
AFIX   0
C23   1    0.312726    0.893259    0.546850    11.00000    0.04156    0.03449 =
         0.03024    0.00495   -0.01000   -0.01882
AFIX  43
H23   2    0.356997    0.966825    0.564134    11.00000    0.03907
AFIX   0
C24   1    0.428317    0.785376    0.491260    11.00000    0.03322    0.04205 =
         0.02787    0.00752   -0.00557   -0.01382
AFIX  43
H24   2    0.551879    0.784751    0.469962    11.00000    0.03932
AFIX   0
C25   1    0.362331    0.678579    0.467024    11.00000    0.04246    0.03479 =
         0.02560   -0.00020   -0.00026   -0.00994
AFIX  43
H25   2    0.440716    0.604808    0.428544    11.00000    0.04650
AFIX   0
C26   1    0.182359    0.678237    0.498468    11.00000    0.04372    0.03068 =
         0.02506    0.00179   -0.00883   -0.01532
AFIX  43
H26   2    0.139392    0.603577    0.481724    11.00000    0.03575
AFIX   0
C27   1    0.064651    0.785830    0.554091    11.00000    0.03040    0.02708 =
         0.02354    0.00776   -0.01161   -0.00815
HKLF 4
REM  Montana01 in P-1
REM R1 =  0.0315 for   3597 Fo > 4sig(Fo)  and  0.0323 for all   3714 data
REM    313 parameters refined using     86 restraints
END
WGHT      0.0341      0.3336
REM Highest difference peak  0.217,  deepest hole -0.140,  1-sigma level  0.032
Q1    1  -0.0337  0.6493  0.6870  11.00000  0.05    0.22
Q2    1   0.2355  0.5386  0.7536  11.00000  0.05    0.22
Q3    1   0.3305  0.3042  0.7193  11.00000  0.05    0.20
Q4    1  -0.2060  0.7295  0.7041  11.00000  0.05    0.19
Q5    1  -0.1229  0.7514  0.6406  11.00000  0.05    0.17
;