##############################################################################
#                                                                            #
# 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
_journal_date_recd_electronic     2014-05-22
_journal_date_accepted     2014-06-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      7
_journal_page_first     o791
_journal_page_last     o792
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814013294
_journal_coeditor_code     ZL2590
_publ_contact_author_name     'Nicholas R. Natale'
_publ_contact_author_address
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
_publ_contact_author_email     'nicholas.natale@mso.umt.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Diethyl 4-(biphenyl-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Steiger, Scott A.' .
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
    'Monacelli, Anthony J.' .
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Li, Chun' .
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Hunting, Janet L.' .
;
Department of Chemistry
Ithaca College
953 Danby Road
Ithaca
NY 14850
USA
;
    'Natale, Nicholas R.' .
;
Department of Biomedical and Pharmaceutical Sciences
The University of Montana
32 Campus Drive
Missoula
MT 59812
USA
;
_publ_section_synopsis     .
_chemical_name_systematic
;
Diethyl 4-(biphenyl-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
;
_chemical_formula_moiety     'C25 H27 N O4'
_chemical_formula_sum     'C25 H27 N O4'
_chemical_formula_iupac     'C25 H27 N O4'
_chemical_formula_weight     405.47
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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     7.3431(3)
_cell_length_b     10.6075(4)
_cell_length_c     13.8449(6)
_cell_angle_alpha     85.762(3)
_cell_angle_beta     88.124(3)
_cell_angle_gamma     73.530(2)
_cell_volume     1031.25(7)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5122
_cell_measurement_theta_min     2.41
_cell_measurement_theta_max     27.39
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     'pale white'
_exptl_crystal_size_max     0.15
_exptl_crystal_size_mid     0.137
_exptl_crystal_size_min     0.125
_exptl_crystal_density_diffrn     1.306
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     432
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2012)'
_shelx_estimated_absorpt_T_min     0.987
_shelx_estimated_absorpt_T_max     0.989
_exptl_absorpt_correction_T_min     0.9187
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     99.99
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker SMART BREEZE CCD'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19956
_diffrn_reflns_av_R_equivalents     0.0718
_diffrn_reflns_theta_min     2.007
_diffrn_reflns_theta_max     27.583
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_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     4752
_reflns_number_gt     2983
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1155
_refine_ls_R_factor_gt     0.0621
_refine_ls_wR_factor_gt     0.1267
_refine_ls_wR_factor_ref     0.1491
_refine_ls_goodness_of_fit_ref     1.015
_refine_ls_restrained_S_all     1.015
_refine_ls_number_reflns     4752
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[\s^2^(Fo^2^)+(0.0537P)^2^+0.8331P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.429
_refine_diff_density_min     -0.369
_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' 0.0033 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'
_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     'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material     'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O3 0.1263(2) 0.73985(17) 0.98682(13) 0.0183(4) Uani d 1 . .
    O O1 0.4574(2) 0.44644(15) 0.75695(12) 0.0149(4) Uani d 1 . .
    O O4 0.2751(2) 0.84869(17) 1.07429(13) 0.0191(4) Uani d 1 . .
    N N1 0.7805(3) 0.68215(19) 0.92579(15) 0.0127(5) Uani d 1 . .
    O O2 0.7739(2) 0.38137(18) 0.73785(14) 0.0248(5) Uani d 1 . .
    C C3 0.4394(3) 0.6641(2) 0.85636(17) 0.0111(5) Uani d 1 . .
    H H3 0.3408 0.6153 0.8619 0.013 Uiso calc 1 . .
    C C4 0.4521(3) 0.7191(2) 0.95378(17) 0.0115(5) Uani d 1 . .
    C C20 0.1965(3) 1.0952(2) 0.55708(17) 0.0118(5) Uani d 1 . .
    C C14 0.3787(3) 0.7763(2) 0.77713(17) 0.0107(5) Uani d 1 . .
    C C25 0.2602(3) 1.0854(2) 0.46091(18) 0.0156(5) Uani d 1 . .
    H H25 0.3384 1.0037 0.4406 0.019 Uiso calc 1 . .
    C C1 0.7918(3) 0.5861(2) 0.86166(17) 0.0122(5) Uani d 1 . .
    C C18 0.2529(3) 0.8563(2) 0.61659(18) 0.0141(5) Uani d 1 . .
    H H18 0.2085 0.8383 0.5569 0.017 Uiso calc 1 . .
    C C5 0.6197(3) 0.7352(2) 0.98050(17) 0.0112(5) Uani d 1 . .
    C C2 0.6293(3) 0.5673(2) 0.83079(17) 0.0118(5) Uani d 1 . .
    C C7 0.2713(3) 0.7670(2) 1.00548(18) 0.0136(5) Uani d 1 . .
    C C21 0.0758(3) 1.2152(2) 0.58379(18) 0.0138(5) Uani d 1 . .
    H H21 0.0290 1.2231 0.6485 0.017 Uiso calc 1 . .
    C C22 0.0236(3) 1.3226(2) 0.51739(19) 0.0167(6) Uani d 1 . .
    H H22 -0.0601 1.4031 0.5365 0.020 Uiso calc 1 . .
    C C17 0.2607(3) 0.9835(2) 0.63075(17) 0.0107(5) Uani d 1 . .
    C C16 0.3313(3) 1.0043(2) 0.71876(18) 0.0144(5) Uani d 1 . .
    H H16 0.3398 1.0897 0.7301 0.017 Uiso calc 1 . .
    C C6 0.6587(3) 0.8067(2) 1.06364(18) 0.0163(6) Uani d 1 . .
    H H6A 0.7962 0.7883 1.0711 0.025 Uiso calc 1 . .
    H H6B 0.6033 0.7768 1.1233 0.025 Uiso calc 1 . .
    H H6C 0.6021 0.9017 1.0508 0.025 Uiso calc 1 . .
    C C19 0.3093(3) 0.7555(2) 0.68872(18) 0.0139(5) Uani d 1 . .
    H H19 0.3004 0.6701 0.6776 0.017 Uiso calc 1 . .
    C C15 0.3893(3) 0.9031(2) 0.78989(18) 0.0125(5) Uani d 1 . .
    H H15 0.4374 0.9204 0.8488 0.015 Uiso calc 1 . .
    C C13 0.9930(3) 0.5135(3) 0.8374(2) 0.0204(6) Uani d 1 . .
    H H13A 1.0506 0.5717 0.7965 0.031 Uiso calc 1 . .
    H H13B 0.9946 0.4360 0.8025 0.031 Uiso calc 1 . .
    H H13C 1.0654 0.4853 0.8972 0.031 Uiso calc 1 . .
    C C8 0.0994(3) 0.9041(2) 1.12773(18) 0.0152(5) Uani d 1 . .
    H H8A 0.0608 0.8337 1.1667 0.018 Uiso calc 1 . .
    H H8B -0.0041 0.9496 1.0825 0.018 Uiso calc 1 . .
    C C10 0.6336(3) 0.4574(2) 0.77147(18) 0.0146(5) Uani d 1 . .
    C C9 0.1404(4) 1.0005(2) 1.19262(19) 0.0195(6) Uani d 1 . .
    H H9A 0.1838 1.0672 1.1532 0.029 Uiso calc 1 . .
    H H9B 0.2395 0.9535 1.2386 0.029 Uiso calc 1 . .
    H H9C 0.0246 1.0433 1.2283 0.029 Uiso calc 1 . .
    C C23 0.0929(4) 1.3132(2) 0.42313(19) 0.0177(6) Uani d 1 . .
    H H23 0.0603 1.3878 0.3781 0.021 Uiso calc 1 . .
    C C24 0.2102(3) 1.1940(2) 0.39484(19) 0.0168(6) Uani d 1 . .
    H H24 0.2564 1.1868 0.3300 0.020 Uiso calc 1 . .
    C C11 0.4471(4) 0.3420(2) 0.69640(18) 0.0176(6) Uani d 1 . .
    H H11A 0.3249 0.3213 0.7091 0.021 Uiso calc 1 . .
    H H11B 0.5507 0.2616 0.7141 0.021 Uiso calc 1 . .
    C C12 0.4631(4) 0.3793(3) 0.59046(19) 0.0245(6) Uani d 1 . .
    H H12A 0.4454 0.3093 0.5526 0.037 Uiso calc 1 . .
    H H12B 0.5891 0.3912 0.5763 0.037 Uiso calc 1 . .
    H H12C 0.3654 0.4618 0.5733 0.037 Uiso calc 1 . .
    H H1 0.893(4) 0.696(3) 0.9411(19) 0.023(8) Uiso d 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
    O3 0.0103(9) 0.0255(10) 0.0221(11) -0.0085(8) 0.0015(7) -0.0084(8)
    O1 0.0152(9) 0.0113(9) 0.0194(10) -0.0046(7) 0.0007(7) -0.0057(7)
    O4 0.0115(9) 0.0269(10) 0.0210(10) -0.0064(8) 0.0055(7) -0.0145(8)
    N1 0.0078(10) 0.0152(11) 0.0168(12) -0.0054(9) 0.0013(8) -0.0049(9)
    O2 0.0154(9) 0.0238(10) 0.0328(12) 0.0018(8) -0.0007(8) -0.0158(9)
    C3 0.0091(11) 0.0108(12) 0.0145(13) -0.0040(9) -0.0004(10) -0.0026(10)
    C4 0.0122(12) 0.0108(12) 0.0110(13) -0.0026(9) 0.0003(9) 0.0000(9)
    C20 0.0106(12) 0.0127(12) 0.0127(13) -0.0044(10) -0.0018(10) -0.0002(10)
    C14 0.0068(11) 0.0106(12) 0.0130(13) 0.0005(9) 0.0019(9) -0.0018(10)
    C25 0.0126(12) 0.0170(13) 0.0181(14) -0.0047(10) -0.0010(10) -0.0039(11)
    C1 0.0108(12) 0.0119(12) 0.0126(13) -0.0016(10) -0.0005(10) 0.0021(10)
    C18 0.0143(12) 0.0145(13) 0.0128(14) -0.0018(10) -0.0022(10) -0.0052(10)
    C5 0.0126(12) 0.0093(11) 0.0118(13) -0.0038(9) -0.0001(10) 0.0011(10)
    C2 0.0131(12) 0.0111(12) 0.0120(13) -0.0050(10) 0.0003(10) 0.0006(10)
    C7 0.0142(12) 0.0131(12) 0.0136(14) -0.0044(10) -0.0007(10) 0.0012(10)
    C21 0.0149(12) 0.0138(12) 0.0126(13) -0.0033(10) -0.0010(10) -0.0028(10)
    C22 0.0154(13) 0.0113(12) 0.0229(15) -0.0020(10) -0.0035(11) -0.0040(11)
    C17 0.0076(11) 0.0116(12) 0.0119(13) -0.0013(9) 0.0018(9) -0.0011(10)
    C16 0.0161(13) 0.0114(12) 0.0168(14) -0.0051(10) 0.0004(10) -0.0032(10)
    C6 0.0125(12) 0.0205(13) 0.0167(14) -0.0050(10) -0.0001(10) -0.0040(11)
    C19 0.0129(12) 0.0091(12) 0.0191(14) -0.0017(10) 0.0003(10) -0.0020(10)
    C15 0.0131(12) 0.0147(12) 0.0109(13) -0.0050(10) -0.0022(10) -0.0033(10)
    C13 0.0133(13) 0.0238(14) 0.0220(15) -0.0003(11) 0.0000(11) -0.0078(12)
    C8 0.0102(12) 0.0200(13) 0.0145(14) -0.0024(10) 0.0040(10) -0.0048(11)
    C10 0.0147(13) 0.0121(12) 0.0156(14) -0.0016(10) -0.0009(10) 0.0002(10)
    C9 0.0163(13) 0.0194(14) 0.0230(16) -0.0041(11) 0.0036(11) -0.0089(11)
    C23 0.0221(14) 0.0155(13) 0.0163(14) -0.0075(11) -0.0065(11) 0.0048(11)
    C24 0.0172(13) 0.0244(14) 0.0108(13) -0.0091(11) -0.0004(10) -0.0011(11)
    C11 0.0228(14) 0.0110(12) 0.0203(15) -0.0052(11) 0.0002(11) -0.0081(11)
    C12 0.0253(15) 0.0329(16) 0.0195(15) -0.0135(13) -0.0007(12) -0.0067(12)
_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
    O3 C7 . 1.219(3) ?
    O1 C10 . 1.354(3) ?
    O1 C11 . 1.458(3) ?
    O4 C7 . 1.340(3) ?
    O4 C8 . 1.459(3) ?
    N1 C1 . 1.383(3) ?
    N1 C5 . 1.383(3) ?
    N1 H1 . 0.91(3) ?
    O2 C10 . 1.217(3) ?
    C3 H3 . 1.0000 ?
    C3 C4 . 1.525(3) ?
    C3 C14 . 1.536(3) ?
    C3 C2 . 1.527(3) ?
    C4 C5 . 1.356(3) ?
    C4 C7 . 1.464(3) ?
    C20 C25 . 1.398(3) ?
    C20 C21 . 1.396(3) ?
    C20 C17 . 1.484(3) ?
    C14 C19 . 1.397(3) ?
    C14 C15 . 1.392(3) ?
    C25 H25 . 0.9500 ?
    C25 C24 . 1.388(4) ?
    C1 C2 . 1.352(3) ?
    C1 C13 . 1.500(3) ?
    C18 H18 . 0.9500 ?
    C18 C17 . 1.395(3) ?
    C18 C19 . 1.389(3) ?
    C5 C6 . 1.502(3) ?
    C2 C10 . 1.468(3) ?
    C21 H21 . 0.9500 ?
    C21 C22 . 1.382(3) ?
    C22 H22 . 0.9500 ?
    C22 C23 . 1.385(4) ?
    C17 C16 . 1.396(3) ?
    C16 H16 . 0.9500 ?
    C16 C15 . 1.385(3) ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C19 H19 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C8 C9 . 1.506(3) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C23 H23 . 0.9500 ?
    C23 C24 . 1.388(3) ?
    C24 H24 . 0.9500 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C11 C12 . 1.500(4) ?
    C12 H12A . 0.9800 ?
    C12 H12B . 0.9800 ?
    C12 H12C . 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
    C10 O1 C11 . . 115.95(18) ?
    C7 O4 C8 . . 117.92(18) ?
    C1 N1 H1 . . 115.9(17) ?
    C5 N1 C1 . . 123.2(2) ?
    C5 N1 H1 . . 119.4(17) ?
    C4 C3 H3 . . 108.3 ?
    C4 C3 C14 . . 110.48(18) ?
    C4 C3 C2 . . 110.09(19) ?
    C14 C3 H3 . . 108.3 ?
    C2 C3 H3 . . 108.3 ?
    C2 C3 C14 . . 111.20(19) ?
    C5 C4 C3 . . 119.3(2) ?
    C5 C4 C7 . . 124.8(2) ?
    C7 C4 C3 . . 115.4(2) ?
    C25 C20 C17 . . 121.4(2) ?
    C21 C20 C25 . . 118.4(2) ?
    C21 C20 C17 . . 120.2(2) ?
    C19 C14 C3 . . 121.1(2) ?
    C15 C14 C3 . . 121.9(2) ?
    C15 C14 C19 . . 117.0(2) ?
    C20 C25 H25 . . 119.7 ?
    C24 C25 C20 . . 120.5(2) ?
    C24 C25 H25 . . 119.7 ?
    N1 C1 C13 . . 112.5(2) ?
    C2 C1 N1 . . 118.8(2) ?
    C2 C1 C13 . . 128.7(2) ?
    C17 C18 H18 . . 119.6 ?
    C19 C18 H18 . . 119.6 ?
    C19 C18 C17 . . 120.8(2) ?
    N1 C5 C6 . . 112.8(2) ?
    C4 C5 N1 . . 118.6(2) ?
    C4 C5 C6 . . 128.6(2) ?
    C1 C2 C3 . . 119.2(2) ?
    C1 C2 C10 . . 120.9(2) ?
    C10 C2 C3 . . 119.9(2) ?
    O3 C7 O4 . . 121.7(2) ?
    O3 C7 C4 . . 124.1(2) ?
    O4 C7 C4 . . 114.2(2) ?
    C20 C21 H21 . . 119.5 ?
    C22 C21 C20 . . 120.9(2) ?
    C22 C21 H21 . . 119.5 ?
    C21 C22 H22 . . 119.9 ?
    C21 C22 C23 . . 120.2(2) ?
    C23 C22 H22 . . 119.9 ?
    C18 C17 C20 . . 122.8(2) ?
    C18 C17 C16 . . 117.5(2) ?
    C16 C17 C20 . . 119.7(2) ?
    C17 C16 H16 . . 119.3 ?
    C15 C16 C17 . . 121.3(2) ?
    C15 C16 H16 . . 119.3 ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C14 C19 H19 . . 119.1 ?
    C18 C19 C14 . . 121.8(2) ?
    C18 C19 H19 . . 119.1 ?
    C14 C15 H15 . . 119.2 ?
    C16 C15 C14 . . 121.6(2) ?
    C16 C15 H15 . . 119.2 ?
    C1 C13 H13A . . 109.5 ?
    C1 C13 H13B . . 109.5 ?
    C1 C13 H13C . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O4 C8 H8A . . 110.5 ?
    O4 C8 H8B . . 110.5 ?
    O4 C8 C9 . . 106.34(19) ?
    H8A C8 H8B . . 108.7 ?
    C9 C8 H8A . . 110.5 ?
    C9 C8 H8B . . 110.5 ?
    O1 C10 C2 . . 112.0(2) ?
    O2 C10 O1 . . 121.3(2) ?
    O2 C10 C2 . . 126.7(2) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C22 C23 H23 . . 120.2 ?
    C22 C23 C24 . . 119.6(2) ?
    C24 C23 H23 . . 120.2 ?
    C25 C24 C23 . . 120.3(2) ?
    C25 C24 H24 . . 119.9 ?
    C23 C24 H24 . . 119.9 ?
    O1 C11 H11A . . 109.1 ?
    O1 C11 H11B . . 109.1 ?
    O1 C11 C12 . . 112.4(2) ?
    H11A C11 H11B . . 107.9 ?
    C12 C11 H11A . . 109.1 ?
    C12 C11 H11B . . 109.1 ?
    C11 C12 H12A . . 109.5 ?
    C11 C12 H12B . . 109.5 ?
    C11 C12 H12C . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 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
    N1 C1 C2 C3 . . . . 8.3(3) ?
    N1 C1 C2 C10 . . . . -173.2(2) ?
    C3 C4 C5 N1 . . . . -10.0(3) ?
    C3 C4 C5 C6 . . . . 169.1(2) ?
    C3 C4 C7 O3 . . . . 16.6(3) ?
    C3 C4 C7 O4 . . . . -161.2(2) ?
    C3 C14 C19 C18 . . . . 179.7(2) ?
    C3 C14 C15 C16 . . . . -178.9(2) ?
    C3 C2 C10 O1 . . . . -8.3(3) ?
    C3 C2 C10 O2 . . . . 172.2(2) ?
    C4 C3 C14 C19 . . . . -163.0(2) ?
    C4 C3 C14 C15 . . . . 16.7(3) ?
    C4 C3 C2 C1 . . . . -31.2(3) ?
    C4 C3 C2 C10 . . . . 150.2(2) ?
    C20 C25 C24 C23 . . . . -1.3(4) ?
    C20 C21 C22 C23 . . . . -0.9(4) ?
    C20 C17 C16 C15 . . . . 178.8(2) ?
    C14 C3 C4 C5 . . . . -91.1(3) ?
    C14 C3 C4 C7 . . . . 81.1(2) ?
    C14 C3 C2 C1 . . . . 91.6(3) ?
    C14 C3 C2 C10 . . . . -87.0(3) ?
    C25 C20 C21 C22 . . . . -1.3(3) ?
    C25 C20 C17 C18 . . . . -50.9(3) ?
    C25 C20 C17 C16 . . . . 129.5(2) ?
    C1 N1 C5 C4 . . . . -17.3(3) ?
    C1 N1 C5 C6 . . . . 163.4(2) ?
    C1 C2 C10 O1 . . . . 173.1(2) ?
    C1 C2 C10 O2 . . . . -6.4(4) ?
    C18 C17 C16 C15 . . . . -0.8(3) ?
    C5 N1 C1 C2 . . . . 18.3(4) ?
    C5 N1 C1 C13 . . . . -160.6(2) ?
    C5 C4 C7 O3 . . . . -171.8(2) ?
    C5 C4 C7 O4 . . . . 10.5(3) ?
    C2 C3 C4 C5 . . . . 32.1(3) ?
    C2 C3 C4 C7 . . . . -155.7(2) ?
    C2 C3 C14 C19 . . . . 74.4(3) ?
    C2 C3 C14 C15 . . . . -105.9(2) ?
    C7 O4 C8 C9 . . . . -174.9(2) ?
    C7 C4 C5 N1 . . . . 178.6(2) ?
    C7 C4 C5 C6 . . . . -2.3(4) ?
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
    C21 H21 O2 1_465 0.95 2.50 3.256(3) 137.0
    C6 H6A O3 1_655 0.98 2.59 3.452(3) 147.0
    C19 H19 O1 . 0.95 2.51 3.227(3) 132.0
    C13 H13B O2 . 0.98 2.11 2.857(3) 131.2
    C8 H8A O2 2_667 0.99 2.55 3.344(3) 136.9
    N1 H1 O3 1_655 0.91(3) 2.03(3) 2.938(3) 173(2)
_iucr_refine_instructions_details
;
TITL AJM_3s2_27_0m in P-1 #2
CELL 0.71073 7.3431 10.6075 13.8449 85.7616 88.124 73.5298
ZERR 2 0.0003 0.0004 0.0006 0.0025 0.0025 0.0023
LATT 1
SFAC C H N O
UNIT 50 54 2 8
EQIV $1 1+X,+Y,+Z
EQIV $2 -1+X,1+Y,+Z
EQIV $3 1-X,1-Y,2-Z
L.S. 10
PLAN  5
SIZE 0.125 0.137 0.15
TEMP -173.16
HTAB C13 O2
HTAB N1 O3_$1
HTAB C21 O2_$2
HTAB C6 O3_$1
HTAB C19 O1
HTAB C8 O2_$3
REM reset to P-1 #2
BOND $H
CONF
HTAB
MORE -1
fmap 2 53
acta
OMIT 0 0 1
WGHT    0.053700    0.833000
FVAR       0.18879
O3    4    0.126289    0.739852    0.986819    11.00000    0.01034    0.02552 =
         0.02208   -0.00845    0.00147   -0.00853
O1    4    0.457394    0.446438    0.756952    11.00000    0.01524    0.01133 =
         0.01937   -0.00566    0.00073   -0.00459
O4    4    0.275060    0.848687    1.074286    11.00000    0.01148    0.02687 =
         0.02102   -0.01450    0.00555   -0.00639
N1    3    0.780485    0.682152    0.925794    11.00000    0.00780    0.01524 =
         0.01678   -0.00494    0.00129   -0.00539
O2    4    0.773907    0.381368    0.737845    11.00000    0.01536    0.02385 =
         0.03278   -0.01578   -0.00075    0.00177
C3    1    0.439407    0.664053    0.856358    11.00000    0.00913    0.01076 =
         0.01446   -0.00265   -0.00038   -0.00400
AFIX  13
H3    2    0.340807    0.615325    0.861913    11.00000   -1.20000
AFIX   0
C4    1    0.452138    0.719130    0.953782    11.00000    0.01223    0.01077 =
         0.01097    0.00001    0.00033   -0.00261
C20   1    0.196468    1.095212    0.557080    11.00000    0.01064    0.01267 =
         0.01275   -0.00020   -0.00180   -0.00445
C14   1    0.378704    0.776346    0.777128    11.00000    0.00676    0.01062 =
         0.01297   -0.00178    0.00186    0.00045
C25   1    0.260238    1.085375    0.460909    11.00000    0.01256    0.01695 =
         0.01810   -0.00385   -0.00100   -0.00470
AFIX  43
H25   2    0.338445    1.003693    0.440641    11.00000   -1.20000
AFIX   0
C1    1    0.791801    0.586126    0.861663    11.00000    0.01076    0.01194 =
         0.01263    0.00210   -0.00046   -0.00164
C18   1    0.252908    0.856277    0.616594    11.00000    0.01427    0.01450 =
         0.01281   -0.00522   -0.00218   -0.00176
AFIX  43
H18   2    0.208500    0.838335    0.556865    11.00000   -1.20000
AFIX   0
C5    1    0.619667    0.735212    0.980503    11.00000    0.01257    0.00926 =
         0.01181    0.00111   -0.00009   -0.00376
C2    1    0.629259    0.567309    0.830795    11.00000    0.01314    0.01112 =
         0.01196    0.00060    0.00028   -0.00502
C7    1    0.271267    0.767013    1.005477    11.00000    0.01415    0.01313 =
         0.01355    0.00124   -0.00069   -0.00436
C21   1    0.075824    1.215176    0.583792    11.00000    0.01489    0.01380 =
         0.01258   -0.00279   -0.00098   -0.00328
AFIX  43
H21   2    0.028988    1.223086    0.648500    11.00000   -1.20000
AFIX   0
C22   1    0.023594    1.322580    0.517394    11.00000    0.01543    0.01125 =
         0.02293   -0.00398   -0.00355   -0.00196
AFIX  43
H22   2   -0.060112    1.403127    0.536471    11.00000   -1.20000
AFIX   0
C17   1    0.260662    0.983464    0.630748    11.00000    0.00756    0.01157 =
         0.01193   -0.00106    0.00180   -0.00125
C16   1    0.331336    1.004345    0.718756    11.00000    0.01611    0.01136 =
         0.01681   -0.00322    0.00039   -0.00512
AFIX  43
H16   2    0.339839    1.089738    0.730053    11.00000   -1.20000
AFIX   0
C6    1    0.658721    0.806706    1.063640    11.00000    0.01249    0.02047 =
         0.01668   -0.00400   -0.00008   -0.00496
AFIX 137
H6A   2    0.796215    0.788316    1.071145    11.00000   -1.50000
H6B   2    0.603284    0.776760    1.123255    11.00000   -1.50000
H6C   2    0.602144    0.901686    1.050763    11.00000   -1.50000
AFIX   0
C19   1    0.309291    0.755498    0.688720    11.00000    0.01294    0.00906 =
         0.01911   -0.00203    0.00030   -0.00173
AFIX  43
H19   2    0.300413    0.670130    0.677631    11.00000   -1.20000
AFIX   0
C15   1    0.389278    0.903054    0.789894    11.00000    0.01312    0.01470 =
         0.01088   -0.00333   -0.00220   -0.00497
AFIX  43
H15   2    0.437400    0.920423    0.848825    11.00000   -1.20000
AFIX   0
C13   1    0.993037    0.513469    0.837364    11.00000    0.01325    0.02382 =
         0.02204   -0.00783    0.00000   -0.00027
AFIX 137
H13A  2    1.050568    0.571661    0.796484    11.00000   -1.50000
H13B  2    0.994598    0.436029    0.802526    11.00000   -1.50000
H13C  2    1.065397    0.485255    0.897210    11.00000   -1.50000
AFIX   0
C8    1    0.099422    0.904134    1.127731    11.00000    0.01025    0.02001 =
         0.01448   -0.00476    0.00401   -0.00243
AFIX  23
H8A   2    0.060766    0.833735    1.166715    11.00000   -1.20000
H8B   2   -0.004080    0.949556    1.082545    11.00000   -1.20000
AFIX   0
C10   1    0.633568    0.457386    0.771468    11.00000    0.01467    0.01206 =
         0.01556    0.00019   -0.00091   -0.00157
C9    1    0.140423    1.000450    1.192618    11.00000    0.01626    0.01941 =
         0.02298   -0.00892    0.00363   -0.00406
AFIX 137
H9A   2    0.183849    1.067214    1.153213    11.00000   -1.50000
H9B   2    0.239495    0.953454    1.238576    11.00000   -1.50000
H9C   2    0.024598    1.043342    1.228277    11.00000   -1.50000
AFIX   0
C23   1    0.092887    1.313177    0.423126    11.00000    0.02213    0.01554 =
         0.01627    0.00478   -0.00653   -0.00747
AFIX  43
H23   2    0.060328    1.387850    0.378103    11.00000   -1.20000
AFIX   0
C24   1    0.210175    1.194000    0.394842    11.00000    0.01724    0.02437 =
         0.01077   -0.00114   -0.00038   -0.00905
AFIX  43
H24   2    0.256356    1.186778    0.329992    11.00000   -1.20000
AFIX   0
C11   1    0.447090    0.341992    0.696398    11.00000    0.02282    0.01103 =
         0.02027   -0.00813    0.00021   -0.00522
AFIX  23
H11A  2    0.324877    0.321319    0.709142    11.00000   -1.20000
H11B  2    0.550700    0.261558    0.714101    11.00000   -1.20000
AFIX   0
C12   1    0.463133    0.379320    0.590464    11.00000    0.02526    0.03290 =
         0.01947   -0.00669   -0.00067   -0.01349
AFIX 137
H12A  2    0.445363    0.309336    0.552568    11.00000   -1.50000
H12B  2    0.589068    0.391241    0.576298    11.00000   -1.50000
H12C  2    0.365446    0.461767    0.573333    11.00000   -1.50000
AFIX   0
H1    2    0.892953    0.695837    0.941147    11.00000    0.02343
HKLF 4
REM  AJM_3s2_27_0m in P-1 #2
REM R1 =  0.0621 for    2983 Fo > 4sig(Fo)  and  0.1155 for all    4752 data
REM    279 parameters refined using      0 restraints
END
;