##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
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#                                                                            #
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#                                                                            #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2006-12-18
_journal_date_accepted     2006-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      2
_journal_page_first     o470
_journal_page_last     o471
_journal_paper_category     EO
_journal_coeditor_code     HG2160
_publ_contact_author_name     'Gardiner, M. G.'
_publ_contact_author_address
;
School of Chemistry
University of Tasmania
Private Bag 75
Hobart
Tasmania 7001
Australia
;
_publ_contact_author_email     michael.gardiner@utas.edu.au
_publ_contact_author_fax     (+61)-03-6226-2858
_publ_contact_author_phone     (+61)-03-6226-2404
_publ_section_title
;
Methyl 4-p-tolyl-1H-pyrrole-2-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Michael G. Gardiner'
;
School of Chemistry
University of Tasmania
Private Bag 75
Hobart
Tasmania 7001
Australia
;
    'Roderick C. Jones'
;
School of Chemistry
University of Tasmania
Private Bag 75
Hobart
Tasmania 7001
Australia
;
    'Sarah Ng'
;
School of Chemistry
University of Tasmania
Private Bag 75
Hobart
Tasmania 7001
Australia
;
    'Jason A. Smith'
;
School of Chemistry
University of Tasmania
Private Bag 75
Hobart
Tasmania 7001
Australia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
Methyl 4-p-tolyl-1H-pyrrole-2-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H13 N O2'
_chemical_formula_sum     'C13 H13 N O2'
_chemical_formula_iupac     'C13 H13 N O2'
_chemical_formula_weight     215.24
_chemical_melting_point        .448E-305
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.7119(15)
_cell_length_b     5.4554(11)
_cell_length_c     26.385(5)
_cell_angle_alpha     90.00
_cell_angle_beta     94.61(3)
_cell_angle_gamma     90.00
_cell_volume     1106.5(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.768
_cell_measurement_theta_max     14.247
_cell_measurement_temperature     193(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.55
_exptl_crystal_size_min     0.45
_exptl_crystal_density_diffrn     1.292
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃, δ, p.p.m.):
2.35 (3H, s), 3.89 (3H, s), 7.19 (3H, m), 7.22 (1H, dd, J 3.0, 1.5 Hz), 7.43
(2H, m), 9.32 (1H, bs); ¹³C NMR (75 MHz, CDCl₃, δ, p.p.m.): 21.3, 51.4,
112.7, 119.6, 125.4, 127.1, 129.6, 131.8, 136.3, 138.4, 162.2; IR (Medium?, \v,
cm⁻¹): 3320, 1682, 1134, 803, 758.
;
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius TurboCAD-4'
_diffrn_measurement_method     'non-profiled ω/2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     1975
_diffrn_reflns_av_R_equivalents     0.0200
_diffrn_reflns_av_sigmaI/netI     0.0152
_diffrn_reflns_theta_min     1.55
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     31
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 All hydrogens were calculated using the riding model of shelxl. Disorder
was apparent in both of the methyl groups, and was modelled using a 50:50%
site occupacy model (HFIX 123).
;
_reflns_number_total     1931
_reflns_number_gt     1648
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0581
_refine_ls_R_factor_gt     0.0440
_refine_ls_wR_factor_gt     0.1163
_refine_ls_wR_factor_ref     0.1352
_refine_ls_goodness_of_fit_ref     1.082
_refine_ls_restrained_S_all     1.082
_refine_ls_number_reflns     1931
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0637P)²+0.8352P] 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     0.247
_refine_diff_density_min     -0.273
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.028(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
X-SEED (Barbour, 2001) and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.85678(19) 0.7428(3) -0.01239(5) 0.0379(4) Uani d . 1 . .
    O O2 0.74376(18) 0.4260(3) 0.02886(5) 0.0348(4) Uani d . 1 . .
    N N1 0.9777(2) 0.9395(3) 0.08533(6) 0.0318(4) Uani d . 1 . .
    H H1 0.9992 1.0434 0.0611 0.038 Uiso calc R 1 . .
    C C1 0.8911(2) 0.7211(4) 0.07833(7) 0.0270(4) Uani d . 1 . .
    C C2 0.8835(2) 0.6136(4) 0.12571(7) 0.0276(5) Uani d . 1 . .
    H H2 0.8302 0.4611 0.1323 0.033 Uiso calc R 1 . .
    C C3 0.9689(2) 0.7700(3) 0.16268(7) 0.0264(4) Uani d . 1 . .
    C C4 1.0251(3) 0.9699(4) 0.13582(8) 0.0309(5) Uani d . 1 . .
    H H4 1.0870 1.1066 0.1504 0.037 Uiso calc R 1 . .
    C C5 0.8314(2) 0.6365(4) 0.02729(7) 0.0283(5) Uani d . 1 . .
    C C6 0.6797(3) 0.3219(4) -0.01974(8) 0.0393(5) Uani d . 1 . .
    H H6A 0.6178 0.1687 -0.0141 0.059 Uiso calc PR 0.50 . .
    H H6B 0.7779 0.2886 -0.0401 0.059 Uiso calc PR 0.50 . .
    H H6C 0.6001 0.4382 -0.0379 0.059 Uiso calc PR 0.50 . .
    H H6D 0.7128 0.4283 -0.0473 0.059 Uiso calc PR 0.50 . .
    H H6E 0.5527 0.3084 -0.0213 0.059 Uiso calc PR 0.50 . .
    H H6F 0.7304 0.1588 -0.0235 0.059 Uiso calc PR 0.50 . .
    C C7 0.9896(2) 0.7311(4) 0.21863(7) 0.0262(5) Uani d . 1 . .
    C C8 0.9149(3) 0.5280(4) 0.24071(7) 0.0299(5) Uani d . 1 . .
    H H8 0.8535 0.4107 0.2196 0.036 Uiso calc R 1 . .
    C C9 0.9293(3) 0.4951(4) 0.29334(7) 0.0318(5) Uani d . 1 . .
    H H9 0.8784 0.3543 0.3073 0.038 Uiso calc R 1 . .
    C C10 1.0164(3) 0.6631(4) 0.32602(7) 0.0317(5) Uani d . 1 . .
    C C11 1.0924(3) 0.8637(4) 0.30385(8) 0.0365(5) Uani d . 1 . .
    H H11 1.1542 0.9806 0.3250 0.044 Uiso calc R 1 . .
    C C12 1.0799(3) 0.8971(4) 0.25129(8) 0.0324(5) Uani d . 1 . .
    H H12 1.1338 1.0356 0.2374 0.039 Uiso calc R 1 . .
    C C13 1.0260(3) 0.6242(5) 0.38335(8) 0.0465(6) Uani d . 1 . .
    H H13A 1.0916 0.7588 0.4004 0.070 Uiso calc PR 0.50 . .
    H H13B 1.0846 0.4684 0.3919 0.070 Uiso calc PR 0.50 . .
    H H13C 0.9081 0.6204 0.3947 0.070 Uiso calc PR 0.50 . .
    H H13D 0.9646 0.4729 0.3909 0.070 Uiso calc PR 0.50 . .
    H H13E 0.9716 0.7633 0.3994 0.070 Uiso calc PR 0.50 . .
    H H13F 1.1481 0.6114 0.3966 0.070 Uiso calc PR 0.50 . .
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 0.0497(9) 0.0400(9) 0.0242(8) -0.0044(7) 0.0048(6) 0.0047(6)
    O2 0.0418(8) 0.0355(8) 0.0269(8) -0.0059(6) 0.0018(6) 0.0000(6)
    N1 0.0400(9) 0.0306(9) 0.0256(9) -0.0021(7) 0.0071(7) 0.0056(7)
    C1 0.0286(9) 0.0288(10) 0.0238(10) 0.0016(8) 0.0043(7) 0.0006(8)
    C2 0.0315(10) 0.0263(10) 0.0255(10) 0.0012(8) 0.0054(8) 0.0028(8)
    C3 0.0260(9) 0.0277(10) 0.0260(10) 0.0034(8) 0.0046(7) 0.0041(8)
    C4 0.0343(10) 0.0296(10) 0.0291(10) -0.0019(8) 0.0040(8) 0.0009(9)
    C5 0.0285(9) 0.0300(10) 0.0270(11) 0.0046(8) 0.0061(8) 0.0021(8)
    C6 0.0415(11) 0.0406(12) 0.0354(12) -0.0022(10) 0.0007(9) -0.0065(10)
    C7 0.0255(9) 0.0270(10) 0.0262(10) 0.0043(7) 0.0026(7) 0.0011(8)
    C8 0.0333(10) 0.0325(10) 0.0234(10) -0.0035(9) -0.0006(8) 0.0023(8)
    C9 0.0337(10) 0.0354(11) 0.0265(10) -0.0019(9) 0.0032(8) 0.0084(9)
    C10 0.0317(10) 0.0395(11) 0.0238(10) 0.0082(9) 0.0012(8) 0.0008(9)
    C11 0.0403(11) 0.0344(11) 0.0338(12) 0.0009(9) -0.0031(9) -0.0047(9)
    C12 0.0378(11) 0.0288(10) 0.0302(11) -0.0017(8) 0.0003(8) 0.0024(8)
    C13 0.0475(13) 0.0640(16) 0.0278(12) 0.0058(12) 0.0015(9) 0.0007(11)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
 Specified hydrogen bonds (with esds except fixed and riding H)
  D-H          H...A        D...A        <(DHA)
  0.88         2.12         2.955(2)     159.3        N1-H1...O1_$2
 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
  6.5787 (0.0049) x - 2.8266 (0.0042) y - 3.4417 (0.0202) z = 3.6980 (0.0086)
 *   -0.0064 (0.0013)  C7
 *    0.0002 (0.0013)  C8
 *    0.0068 (0.0014)  C9
 *   -0.0076 (0.0014)  C10
 *    0.0014 (0.0014)  C11
 *    0.0056 (0.0014)  C12
     -0.0599 (0.0029)  C3
 Rms deviation of fitted atoms =   0.0055
  6.7665 (0.0051) x - 2.5462 (0.0050) y - 4.7803 (0.0246) z = 3.8172 (0.0082)
 Angle to previous plane (with approximate esd) =  4.30 ( 0.12 )
 *   -0.0016 (0.0011)  N1
 *    0.0022 (0.0011)  C1
 *   -0.0019 (0.0011)  C2
 *    0.0010 (0.0011)  C3
 *    0.0004 (0.0012)  C4
      0.0574 (0.0032)  C5
     -0.0275 (0.0032)  C7
 Rms deviation of fitted atoms =   0.0015
  6.6483 (0.0049) x - 2.7544 (0.0042) y - 2.9755 (0.0401) z = 3.6891 (0.0055)
 Angle to previous plane (with approximate esd) =  4.52 ( 0.12 )
 *    0.0040 (0.0011)  C5
 *    0.0017 (0.0005)  C6
 *   -0.0021 (0.0006)  O1
 *   -0.0035 (0.0010)  O2
      0.0162 (0.0038)  C1
 Rms deviation of fitted atoms =   0.0030
  6.6675 (0.0039) x - 2.7071 (0.0026) y - 3.9176 (0.0050) z = 3.7166 (0.0036)
 Angle to previous plane (with approximate esd) =  2.11 ( 0.09 )
 *   -0.0753 (0.0015)  N1
 *    0.0337 (0.0014)  O1
 *   -0.0238 (0.0014)  O2
 *   -0.0339 (0.0017)  C1
 *    0.0210 (0.0018)  C2
 *    0.0221 (0.0017)  C3
 *   -0.0394 (0.0017)  C4
 *   -0.0032 (0.0017)  C5
 *    0.0211 (0.0016)  C6
 *    0.0462 (0.0017)  C7
 *    0.0113 (0.0018)  C8
 *   -0.0097 (0.0017)  C9
 *   -0.0119 (0.0018)  C10
 *    0.0384 (0.0018)  C11
 *    0.0705 (0.0019)  C12
 *   -0.0672 (0.0019)  C13
 Rms deviation of fitted atoms =   0.0395
  6.8164 (0.0051) x - 2.5339 (0.0052) y - 3.3149 (0.0221) z = 3.9833 (0.0072)
 Angle to previous plane (with approximate esd) =  2.55 ( 0.10 )
 *   -0.0185 (0.0004)  H1
 *    0.0178 (0.0006)  N1
 *    0.0043 (0.0010)  C1
 *   -0.0193 (0.0013)  C5
 *    0.0158 (0.0007)  O1
      0.6170 (0.0040)  H1_$2
      0.5807 (0.0049)  N1_$2
      0.5942 (0.0041)  C1_$2
      0.6178 (0.0046)  C5_$2
      0.5827 (0.0044)  O1_$2
 Rms deviation of fitted atoms =   0.0161
;
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 . 1.226(2) yes
    O2 C5 . 1.335(2) yes
    O2 C6 . 1.452(3) yes
    N1 C4 . 1.363(3) yes
    N1 C1 . 1.371(3) yes
    N1 H1 . 0.8800 ?
    C1 C2 . 1.387(3) yes
    C1 C5 . 1.462(3) yes
    C2 C3 . 1.418(3) yes
    C2 H2 . 0.9500 ?
    C3 C4 . 1.389(3) yes
    C3 C7 . 1.487(3) yes
    C4 H4 . 0.9500 ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C6 H6D . 0.9800 ?
    C6 H6E . 0.9800 ?
    C6 H6F . 0.9800 ?
    C7 C12 . 1.397(3) ?
    C7 C8 . 1.397(3) ?
    C8 C9 . 1.396(3) ?
    C8 H8 . 0.9500 ?
    C9 C10 . 1.393(3) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.393(3) ?
    C10 C13 . 1.523(3) ?
    C11 C12 . 1.394(3) ?
    C11 H11 . 0.9500 ?
    C12 H12 . 0.9500 ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C13 H13D . 0.9800 ?
    C13 H13E . 0.9800 ?
    C13 H13F . 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
    C5 O2 C6 . . 116.49(16) yes
    C4 N1 C1 . . 109.06(16) yes
    C4 N1 H1 . . 125.5 ?
    C1 N1 H1 . . 125.5 ?
    N1 C1 C2 . . 107.56(17) yes
    N1 C1 C5 . . 120.81(17) yes
    C2 C1 C5 . . 131.59(19) yes
    C1 C2 C3 . . 108.34(17) yes
    C1 C2 H2 . . 125.8 ?
    C3 C2 H2 . . 125.8 ?
    C4 C3 C2 . . 105.56(17) yes
    C4 C3 C7 . . 127.28(18) yes
    C2 C3 C7 . . 127.14(17) yes
    N1 C4 C3 . . 109.48(18) yes
    N1 C4 H4 . . 125.3 ?
    C3 C4 H4 . . 125.3 ?
    O1 C5 O2 . . 123.31(19) yes
    O1 C5 C1 . . 125.24(19) yes
    O2 C5 C1 . . 111.45(16) yes
    O2 C6 H6A . . 109.5 ?
    O2 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    O2 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    O2 C6 H6D . . 109.5 ?
    H6A C6 H6D . . 141.1 ?
    H6B C6 H6D . . 56.3 ?
    H6C C6 H6D . . 56.3 ?
    O2 C6 H6E . . 109.5 ?
    H6A C6 H6E . . 56.3 ?
    H6B C6 H6E . . 141.1 ?
    H6C C6 H6E . . 56.3 ?
    H6D C6 H6E . . 109.5 ?
    O2 C6 H6F . . 109.5 ?
    H6A C6 H6F . . 56.3 ?
    H6B C6 H6F . . 56.3 ?
    H6C C6 H6F . . 141.1 ?
    H6D C6 H6F . . 109.5 ?
    H6E C6 H6F . . 109.5 ?
    C12 C7 C8 . . 117.30(18) ?
    C12 C7 C3 . . 121.89(18) ?
    C8 C7 C3 . . 120.80(17) ?
    C9 C8 C7 . . 120.96(19) ?
    C9 C8 H8 . . 119.5 ?
    C7 C8 H8 . . 119.5 ?
    C10 C9 C8 . . 121.79(19) ?
    C10 C9 H9 . . 119.1 ?
    C8 C9 H9 . . 119.1 ?
    C11 C10 C9 . . 117.08(19) ?
    C11 C10 C13 . . 122.5(2) ?
    C9 C10 C13 . . 120.4(2) ?
    C10 C11 C12 . . 121.5(2) ?
    C10 C11 H11 . . 119.2 ?
    C12 C11 H11 . . 119.2 ?
    C11 C12 C7 . . 121.35(19) ?
    C11 C12 H12 . . 119.3 ?
    C7 C12 H12 . . 119.3 ?
    C10 C13 H13A . . 109.5 ?
    C10 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    C10 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    C10 C13 H13D . . 109.5 ?
    H13A C13 H13D . . 141.1 ?
    H13B C13 H13D . . 56.3 ?
    H13C C13 H13D . . 56.3 ?
    C10 C13 H13E . . 109.5 ?
    H13A C13 H13E . . 56.3 ?
    H13B C13 H13E . . 141.1 ?
    H13C C13 H13E . . 56.3 ?
    H13D C13 H13E . . 109.5 ?
    C10 C13 H13F . . 109.5 ?
    H13A C13 H13F . . 56.3 ?
    H13B C13 H13F . . 56.3 ?
    H13C C13 H13F . . 141.1 ?
    H13D C13 H13F . . 109.5 ?
    H13E C13 H13F . . 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
    C4 N1 C1 C2 . . . . 0.4(2) ?
    C4 N1 C1 C5 . . . . -177.43(17) ?
    N1 C1 C2 C3 . . . . -0.4(2) ?
    C5 C1 C2 C3 . . . . 177.08(18) ?
    C1 C2 C3 C4 . . . . 0.3(2) ?
    C1 C2 C3 C7 . . . . 178.75(17) ?
    C1 N1 C4 C3 . . . . -0.2(2) ?
    C2 C3 C4 N1 . . . . 0.0(2) ?
    C7 C3 C4 N1 . . . . -178.53(17) ?
    C6 O2 C5 O1 . . . . 0.9(3) ?
    C6 O2 C5 C1 . . . . -179.22(16) ?
    N1 C1 C5 O1 . . . . 2.6(3) yes
    C2 C1 C5 O1 . . . . -174.6(2) yes
    N1 C1 C5 O2 . . . . -177.28(16) yes
    C2 C1 C5 O2 . . . . 5.5(3) yes
    C4 C3 C7 C12 . . . . -3.1(3) yes
    C2 C3 C7 C12 . . . . 178.76(18) yes
    C4 C3 C7 C8 . . . . 175.30(18) yes
    C2 C3 C7 C8 . . . . -2.9(3) yes
    C12 C7 C8 C9 . . . . 0.5(3) ?
    C3 C7 C8 C9 . . . . -177.92(17) ?
    C7 C8 C9 C10 . . . . 0.7(3) ?
    C8 C9 C10 C11 . . . . -1.4(3) ?
    C8 C9 C10 C13 . . . . 178.60(19) ?
    C9 C10 C11 C12 . . . . 0.9(3) ?
    C13 C10 C11 C12 . . . . -179.13(19) ?
    C10 C11 C12 C7 . . . . 0.4(3) ?
    C8 C7 C12 C11 . . . . -1.1(3) ?
    C3 C7 C12 C11 . . . . 177.37(18) ?
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
    N1 H1 O1 3_775 0.88 2.12 2.955(2) 159.3
