##############################################################################
#                                                                            #
# 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     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.3
_journal_date_recd_electronic     2014-07-24
_journal_date_accepted     2014-07-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      9
_journal_page_first     o968
_journal_page_last     o969
_journal_paper_category     HO
_journal_paper_doi     10.1107/S1600536814017188
_journal_coeditor_code     HB7260
_publ_contact_author_name     'Dr P.L. Nilantha Lakshman'
_publ_contact_author_address
;
Department of Food science and Technology
University of Ruhuna
Mapalana
Kamburupitiya (81100)
Sri Lanka
;
_publ_contact_author_email     'plakshmannilantha@ymail.com'
_publ_contact_author_fax     '+94-41-2292384'
_publ_contact_author_phone     '+94-41-2292200'
_publ_section_title
;\
Crystal structure of
2-(2-bromophenyl)-4-(1<i>H</i>-indol-3-yl)-6-(thiophen-2-yl)pyridine-3-\
carbonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Vishnupriya, R.' .
;
Department of Physics
The Madura College,
Madurai 625 011
India
;
    'Suresh, J.' .
;
Department of Physics
The Madura College,
Madurai 625 011
India
;
    'Shanmugavel Bharkavi' .
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
    'Subbu Perumal' .
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
    'Lakshman, P. L. Nilantha' .
;
Department of Food Science and Technology
University of Ruhuna
Mapalana
Kamburupitiya 81100
Sri Lanka
;
_publ_section_synopsis     .
data_I
_database_code_depnum_ccdc_archive 'CCDC 1015962'
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;\
2-(2-Bromophenyl)-4-(1<i>H</i>-indol-3-yl)-6-(thiophen-2-yl)pyridine-\
3-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H14 Br N3 S'
_chemical_formula_sum     'C24 H14 Br N3 S'
_chemical_formula_iupac     'C24 H14 Br N3 S'
_chemical_formula_weight     456.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.470(5)
_cell_length_b     21.353(5)
_cell_length_c     9.292(5)
_cell_angle_alpha     90.00
_cell_angle_beta     107.710(5)
_cell_angle_gamma     90.00
_cell_volume     1978.9(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2000
_cell_measurement_theta_min     2
_cell_measurement_theta_max     27
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.17
_exptl_crystal_density_diffrn     1.532
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     920
_exptl_absorpt_coefficient_mu     2.198
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9583
_exptl_absorpt_correction_T_max     0.9863
_exptl_special_details     ?
_diffrn_ambient_temperature     293(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     'Bruker Kappa APEXII'
_diffrn_measurement_method     '\w and \f'
_diffrn_detector_area_resol_mean     0
_diffrn_reflns_number     17079
_diffrn_reflns_av_R_equivalents     0.0406
_diffrn_reflns_av_sigmaI/netI     0.0461
_diffrn_reflns_theta_min     1.91
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     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     4305
_reflns_number_gt     2837
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0851
_refine_ls_R_factor_gt     0.0457
_refine_ls_wR_factor_gt     0.1051
_refine_ls_wR_factor_ref     0.1207
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     4305
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.4334P] 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     0.475
_refine_diff_density_min     -0.354
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.2901 2.4595
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.2640(3) 0.50193(12) 0.7417(3) 0.0386(7) Uani d . 1 1 . .
    C C2 0.3077(3) 0.44165(13) 0.7289(3) 0.0425(7) Uani d . 1 1 . .
    H H2 0.3543 0.4194 0.8149 0.051 Uiso calc R 1 1 . .
    C C3 0.2818(3) 0.41458(12) 0.5880(3) 0.0390(7) Uani d . 1 1 . .
    C C4 0.2078(3) 0.45002(12) 0.4630(3) 0.0368(6) Uani d . 1 1 . .
    C C5 0.1664(3) 0.51133(12) 0.4822(3) 0.0371(6) Uani d . 1 1 . .
    C C11 0.2890(3) 0.53182(14) 0.8898(3) 0.0432(7) Uani d . 1 1 . .
    C C12 0.3376(3) 0.50426(15) 1.0315(3) 0.0481(8) Uani d . 1 1 . .
    H H12 0.3625 0.4624 1.0484 0.058 Uiso calc R 1 1 . .
    C C13 0.3439(4) 0.54874(19) 1.1471(3) 0.0622(9) Uani d . 1 1 . .
    H H13 0.3745 0.5393 1.2496 0.075 Uiso calc R 1 1 . .
    C C14 0.3011(4) 0.60608(18) 1.0930(4) 0.0651(10) Uani d . 1 1 . .
    H H14 0.2995 0.6405 1.1538 0.078 Uiso calc R 1 1 . .
    C C31 0.3330(3) 0.35097(13) 0.5742(3) 0.0402(7) Uani d . 1 1 . .
    C C32 0.2810(4) 0.30034(14) 0.6331(3) 0.0555(8) Uani d . 1 1 . .
    H H32 0.2108 0.3068 0.6733 0.067 Uiso calc R 1 1 . .
    C C33 0.3322(4) 0.24105(16) 0.6326(4) 0.0697(11) Uani d . 1 1 . .
    H H33 0.2958 0.2078 0.6716 0.084 Uiso calc R 1 1 . .
    C C34 0.4351(5) 0.23060(17) 0.5759(4) 0.0736(11) Uani d . 1 1 . .
    H H34 0.4695 0.1904 0.5774 0.088 Uiso calc R 1 1 . .
    C C35 0.4892(4) 0.27918(16) 0.5159(4) 0.0650(10) Uani d . 1 1 . .
    H H35 0.5597 0.2721 0.4766 0.078 Uiso calc R 1 1 . .
    C C36 0.4366(3) 0.33884(13) 0.5151(3) 0.0466(7) Uani d . 1 1 . .
    C C41 0.1792(3) 0.42163(13) 0.3172(3) 0.0451(7) Uani d . 1 1 . .
    C C51 0.0943(3) 0.55225(13) 0.3593(3) 0.0380(6) Uani d . 1 1 . .
    C C52 0.0877(3) 0.61968(13) 0.3648(3) 0.0404(7) Uani d . 1 1 . .
    C C53 0.1419(3) 0.66595(14) 0.4726(3) 0.0497(8) Uani d . 1 1 . .
    H H53 0.1932 0.6550 0.5699 0.060 Uiso calc R 1 1 . .
    C C54 0.1186(4) 0.72736(15) 0.4329(4) 0.0614(9) Uani d . 1 1 . .
    H H54 0.1561 0.7581 0.5041 0.074 Uiso calc R 1 1 . .
    C C55 0.0405(4) 0.74537(17) 0.2892(4) 0.0657(10) Uani d . 1 1 . .
    H H55 0.0253 0.7877 0.2669 0.079 Uiso calc R 1 1 . .
    C C56 -0.0136(4) 0.70208(16) 0.1814(4) 0.0581(9) Uani d . 1 1 . .
    H H56 -0.0650 0.7140 0.0849 0.070 Uiso calc R 1 1 . .
    C C57 0.0104(3) 0.63913(14) 0.2198(3) 0.0451(7) Uani d . 1 1 . .
    C C58 0.0214(3) 0.53562(14) 0.2152(3) 0.0452(7) Uani d . 1 1 . .
    H H58 0.0082 0.4948 0.1791 0.054 Uiso calc R 1 1 . .
    N N1 0.1961(2) 0.53636(10) 0.6215(2) 0.0386(6) Uani d . 1 1 . .
    N N2 0.1568(3) 0.39821(12) 0.2015(3) 0.0630(8) Uani d . 1 1 . .
    N N3 -0.0283(3) 0.58711(12) 0.1335(3) 0.0500(7) Uani d . 1 1 . .
    H H3 -0.0773 0.5870 0.0405 0.060 Uiso calc R 1 1 . .
    S S 0.25060(12) 0.60852(4) 0.90204(10) 0.0706(3) Uani d . 1 1 . .
    Br Br 0.51614(4) 0.404354(16) 0.43368(4) 0.06285(16) Uani d . 1 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
    C1 0.0378(18) 0.0460(16) 0.0330(14) -0.0027(13) 0.0123(13) 0.0018(13)
    C2 0.049(2) 0.0473(17) 0.0288(14) 0.0025(14) 0.0084(13) 0.0054(12)
    C3 0.0397(18) 0.0415(15) 0.0365(15) -0.0016(13) 0.0128(13) 0.0067(12)
    C4 0.0403(18) 0.0393(14) 0.0298(14) -0.0037(13) 0.0094(12) 0.0000(12)
    C5 0.0362(17) 0.0420(15) 0.0330(14) -0.0041(13) 0.0103(12) 0.0019(12)
    C11 0.0382(18) 0.0517(17) 0.0380(16) -0.0058(14) 0.0093(13) -0.0024(13)
    C12 0.054(2) 0.0600(18) 0.0271(14) -0.0014(15) 0.0083(14) -0.0045(14)
    C13 0.059(2) 0.088(3) 0.0347(17) -0.005(2) 0.0078(16) -0.0043(17)
    C14 0.076(3) 0.075(2) 0.0419(18) -0.001(2) 0.0139(18) -0.0232(17)
    C31 0.0467(19) 0.0402(15) 0.0285(14) 0.0000(13) 0.0038(13) 0.0009(12)
    C32 0.062(2) 0.0500(19) 0.0537(19) -0.0032(16) 0.0163(17) 0.0094(15)
    C33 0.087(3) 0.0421(19) 0.071(2) -0.0048(19) 0.012(2) 0.0172(17)
    C34 0.086(3) 0.046(2) 0.080(3) 0.011(2) 0.013(2) 0.0019(18)
    C35 0.070(3) 0.057(2) 0.066(2) 0.0158(18) 0.0176(19) -0.0031(18)
    C36 0.051(2) 0.0464(17) 0.0392(16) -0.0005(15) 0.0082(15) 0.0002(13)
    C41 0.054(2) 0.0375(15) 0.0383(17) 0.0044(14) 0.0051(14) 0.0058(14)
    C51 0.0384(18) 0.0446(15) 0.0318(14) -0.0001(13) 0.0119(13) 0.0035(12)
    C52 0.0407(18) 0.0457(15) 0.0389(16) 0.0046(14) 0.0182(14) 0.0090(13)
    C53 0.056(2) 0.0463(17) 0.0477(18) 0.0001(15) 0.0179(16) 0.0005(14)
    C54 0.072(3) 0.0451(18) 0.073(2) -0.0003(17) 0.031(2) 0.0008(17)
    C55 0.076(3) 0.0490(19) 0.078(3) 0.0099(18) 0.032(2) 0.0204(19)
    C56 0.057(2) 0.061(2) 0.058(2) 0.0113(18) 0.0199(17) 0.0262(18)
    C57 0.0436(19) 0.0540(18) 0.0409(16) 0.0052(15) 0.0177(14) 0.0119(14)
    C58 0.045(2) 0.0494(17) 0.0402(16) 0.0037(14) 0.0111(14) 0.0024(14)
    N1 0.0424(15) 0.0416(13) 0.0316(12) -0.0021(11) 0.0107(11) 0.0006(10)
    N2 0.089(2) 0.0508(16) 0.0405(15) 0.0127(14) 0.0065(15) -0.0049(12)
    N3 0.0488(18) 0.0617(17) 0.0330(13) 0.0058(13) 0.0024(12) 0.0085(12)
    S 0.0982(9) 0.0602(5) 0.0497(5) 0.0089(5) 0.0167(5) -0.0073(4)
    Br 0.0616(3) 0.0661(3) 0.0687(3) -0.00767(17) 0.0314(2) 0.00167(16)
_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
    C1 N1 . 1.345(3) ?
    C1 C2 . 1.383(4) ?
    C1 C11 . 1.466(4) ?
    C2 C3 . 1.380(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.405(4) ?
    C3 C31 . 1.480(4) ?
    C4 C5 . 1.408(4) ?
    C4 C41 . 1.431(4) ?
    C5 N1 . 1.346(3) ?
    C5 C51 . 1.454(4) ?
    C11 C12 . 1.390(4) ?
    C11 S . 1.698(3) ?
    C12 C13 . 1.420(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.347(5) ?
    C13 H13 . 0.9300 ?
    C14 S . 1.691(4) ?
    C14 H14 . 0.9300 ?
    C31 C36 . 1.381(4) ?
    C31 C32 . 1.395(4) ?
    C32 C33 . 1.376(5) ?
    C32 H32 . 0.9300 ?
    C33 C34 . 1.354(6) ?
    C33 H33 . 0.9300 ?
    C34 C35 . 1.378(5) ?
    C34 H34 . 0.9300 ?
    C35 C36 . 1.387(4) ?
    C35 H35 . 0.9300 ?
    C36 Br . 1.899(3) ?
    C41 N2 . 1.143(4) ?
    C51 C58 . 1.371(4) ?
    C51 C52 . 1.443(4) ?
    C52 C53 . 1.399(4) ?
    C52 C57 . 1.407(4) ?
    C53 C54 . 1.364(4) ?
    C53 H53 . 0.9300 ?
    C54 C55 . 1.391(5) ?
    C54 H54 . 0.9300 ?
    C55 C56 . 1.354(5) ?
    C55 H55 . 0.9300 ?
    C56 C57 . 1.394(4) ?
    C56 H56 . 0.9300 ?
    C57 N3 . 1.358(4) ?
    C58 N3 . 1.347(4) ?
    C58 H58 . 0.9300 ?
    N3 H3 . 0.8600 ?
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
    N1 C1 C2 . . 122.8(2) ?
    N1 C1 C11 . . 116.1(2) ?
    C2 C1 C11 . . 121.1(2) ?
    C3 C2 C1 . . 119.8(3) ?
    C3 C2 H2 . . 120.1 ?
    C1 C2 H2 . . 120.1 ?
    C2 C3 C4 . . 117.3(3) ?
    C2 C3 C31 . . 119.7(2) ?
    C4 C3 C31 . . 123.1(2) ?
    C3 C4 C5 . . 120.6(2) ?
    C3 C4 C41 . . 117.3(2) ?
    C5 C4 C41 . . 122.0(2) ?
    N1 C5 C4 . . 120.1(2) ?
    N1 C5 C51 . . 115.4(2) ?
    C4 C5 C51 . . 124.5(2) ?
    C12 C11 C1 . . 127.9(3) ?
    C12 C11 S . . 111.8(2) ?
    C1 C11 S . . 120.3(2) ?
    C11 C12 C13 . . 110.6(3) ?
    C11 C12 H12 . . 124.7 ?
    C13 C12 H12 . . 124.7 ?
    C14 C13 C12 . . 113.1(3) ?
    C14 C13 H13 . . 123.5 ?
    C12 C13 H13 . . 123.5 ?
    C13 C14 S . . 112.5(3) ?
    C13 C14 H14 . . 123.8 ?
    S C14 H14 . . 123.8 ?
    C36 C31 C32 . . 117.3(3) ?
    C36 C31 C3 . . 123.8(3) ?
    C32 C31 C3 . . 118.8(3) ?
    C33 C32 C31 . . 120.8(3) ?
    C33 C32 H32 . . 119.6 ?
    C31 C32 H32 . . 119.6 ?
    C34 C33 C32 . . 120.7(3) ?
    C34 C33 H33 . . 119.7 ?
    C32 C33 H33 . . 119.7 ?
    C33 C34 C35 . . 120.5(3) ?
    C33 C34 H34 . . 119.8 ?
    C35 C34 H34 . . 119.8 ?
    C34 C35 C36 . . 118.8(4) ?
    C34 C35 H35 . . 120.6 ?
    C36 C35 H35 . . 120.6 ?
    C31 C36 C35 . . 121.9(3) ?
    C31 C36 Br . . 120.9(2) ?
    C35 C36 Br . . 117.2(3) ?
    N2 C41 C4 . . 179.1(3) ?
    C58 C51 C52 . . 105.9(2) ?
    C58 C51 C5 . . 127.8(3) ?
    C52 C51 C5 . . 126.2(2) ?
    C53 C52 C57 . . 117.9(3) ?
    C53 C52 C51 . . 135.8(3) ?
    C57 C52 C51 . . 106.3(2) ?
    C54 C53 C52 . . 119.0(3) ?
    C54 C53 H53 . . 120.5 ?
    C52 C53 H53 . . 120.5 ?
    C53 C54 C55 . . 122.0(3) ?
    C53 C54 H54 . . 119.0 ?
    C55 C54 H54 . . 119.0 ?
    C56 C55 C54 . . 120.9(3) ?
    C56 C55 H55 . . 119.6 ?
    C54 C55 H55 . . 119.6 ?
    C55 C56 C57 . . 117.8(3) ?
    C55 C56 H56 . . 121.1 ?
    C57 C56 H56 . . 121.1 ?
    N3 C57 C56 . . 129.7(3) ?
    N3 C57 C52 . . 107.8(3) ?
    C56 C57 C52 . . 122.4(3) ?
    N3 C58 C51 . . 110.1(3) ?
    N3 C58 H58 . . 124.9 ?
    C51 C58 H58 . . 124.9 ?
    C1 N1 C5 . . 119.4(2) ?
    C58 N3 C57 . . 109.9(3) ?
    C58 N3 H3 . . 125.1 ?
    C57 N3 H3 . . 125.1 ?
    C14 S C11 . . 92.04(16) ?
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 . . . . 0.0(5) ?
    C11 C1 C2 C3 . . . . 179.6(3) ?
    C1 C2 C3 C4 . . . . -1.7(4) ?
    C1 C2 C3 C31 . . . . 177.8(3) ?
    C2 C3 C4 C5 . . . . 2.1(4) ?
    C31 C3 C4 C5 . . . . -177.3(3) ?
    C2 C3 C4 C41 . . . . -179.0(3) ?
    C31 C3 C4 C41 . . . . 1.6(4) ?
    C3 C4 C5 N1 . . . . -0.8(4) ?
    C41 C4 C5 N1 . . . . -179.7(3) ?
    C3 C4 C5 C51 . . . . 177.5(3) ?
    C41 C4 C5 C51 . . . . -1.4(4) ?
    N1 C1 C11 C12 . . . . 169.4(3) ?
    C2 C1 C11 C12 . . . . -10.2(5) ?
    N1 C1 C11 S . . . . -7.5(4) ?
    C2 C1 C11 S . . . . 172.9(2) ?
    C1 C11 C12 C13 . . . . -178.3(3) ?
    S C11 C12 C13 . . . . -1.2(4) ?
    C11 C12 C13 C14 . . . . 0.5(4) ?
    C12 C13 C14 S . . . . 0.5(4) ?
    C2 C3 C31 C36 . . . . -108.6(3) ?
    C4 C3 C31 C36 . . . . 70.8(4) ?
    C2 C3 C31 C32 . . . . 66.9(4) ?
    C4 C3 C31 C32 . . . . -113.7(3) ?
    C36 C31 C32 C33 . . . . 0.4(5) ?
    C3 C31 C32 C33 . . . . -175.3(3) ?
    C31 C32 C33 C34 . . . . 0.5(5) ?
    C32 C33 C34 C35 . . . . -0.8(6) ?
    C33 C34 C35 C36 . . . . 0.2(6) ?
    C32 C31 C36 C35 . . . . -1.1(4) ?
    C3 C31 C36 C35 . . . . 174.4(3) ?
    C32 C31 C36 Br . . . . -179.4(2) ?
    C3 C31 C36 Br . . . . -3.9(4) ?
    C34 C35 C36 C31 . . . . 0.8(5) ?
    C34 C35 C36 Br . . . . 179.2(3) ?
    N1 C5 C51 C58 . . . . -161.3(3) ?
    C4 C5 C51 C58 . . . . 20.3(5) ?
    N1 C5 C51 C52 . . . . 20.1(4) ?
    C4 C5 C51 C52 . . . . -158.3(3) ?
    C58 C51 C52 C53 . . . . -177.4(3) ?
    C5 C51 C52 C53 . . . . 1.5(5) ?
    C58 C51 C52 C57 . . . . -0.4(3) ?
    C5 C51 C52 C57 . . . . 178.4(3) ?
    C57 C52 C53 C54 . . . . -0.4(4) ?
    C51 C52 C53 C54 . . . . 176.3(3) ?
    C52 C53 C54 C55 . . . . 1.2(5) ?
    C53 C54 C55 C56 . . . . -1.3(5) ?
    C54 C55 C56 C57 . . . . 0.7(5) ?
    C55 C56 C57 N3 . . . . -178.0(3) ?
    C55 C56 C57 C52 . . . . 0.0(5) ?
    C53 C52 C57 N3 . . . . 178.3(3) ?
    C51 C52 C57 N3 . . . . 0.7(3) ?
    C53 C52 C57 C56 . . . . -0.2(4) ?
    C51 C52 C57 C56 . . . . -177.8(3) ?
    C52 C51 C58 N3 . . . . 0.1(3) ?
    C5 C51 C58 N3 . . . . -178.8(3) ?
    C2 C1 N1 C5 . . . . 1.3(4) ?
    C11 C1 N1 C5 . . . . -178.3(2) ?
    C4 C5 N1 C1 . . . . -0.9(4) ?
    C51 C5 N1 C1 . . . . -179.3(2) ?
    C51 C58 N3 C57 . . . . 0.4(4) ?
    C56 C57 N3 C58 . . . . 177.6(3) ?
    C52 C57 N3 C58 . . . . -0.6(4) ?
    C13 C14 S C11 . . . . -1.0(3) ?
    C12 C11 S C14 . . . . 1.3(3) ?
    C1 C11 S C14 . . . . 178.6(3) ?
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
    C53 H53 N1 . 0.93 2.58 3.069(4) 114
    C58 H58 N2 . 0.93 2.55 3.278(4) 135
    N3 H3 N2 3_565 0.86 2.17 3.008(4) 165
    C32 H32 Cg1 3_555 0.93 2.89 3.761(4) 157
_iucr_refine_instructions_details
;
TITL I P 21/n R = 0.06
CELL  0.71073   9.5219  13.8808  12.1140   90.000   97.829   90.000
ZERR     4.00   0.0003   0.0004   0.0003    0.000    0.001    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    F    N    O
UNIT  76   76   4    8    4
MERG   2
FMAP   2
PLAN   20
ACTA
BOND   $H
CONF
L.S.  12
TEMP    20.00
omit -2 54
omit 2 3 2
DFIX  1.35 0.001 C15 F1A C19 F1B
FLAT  0.005 C14 > C19 F1A F1B H15 H19
EADP F1A F1B
WGHT    0.063100    0.716700
EXTI    0.009694
FVAR       0.22990   0.19111
C1    1    0.488231    0.149459    0.478406    11.00000    0.04202    0.03733 =
         0.03611    0.00017    0.00535    0.00366
C2    1    0.566742    0.184099    0.386970    11.00000    0.05243    0.04677 =
         0.03808   -0.00209    0.01166   -0.00083
AFIX  23
H2A   2    0.563589    0.134405    0.330390    11.00000   -1.20000
H2B   2    0.665328    0.194283    0.417070    11.00000   -1.20000
AFIX   0
C3    1    0.507184    0.276917    0.332788    11.00000    0.06246    0.05690 =
         0.03992    0.00652    0.00202   -0.00451
AFIX  23
H3A   2    0.569307    0.298266    0.280507    11.00000   -1.20000
H3B   2    0.415489    0.263030    0.290413    11.00000   -1.20000
AFIX   0
C4    1    0.489559    0.358827    0.412247    11.00000    0.06447    0.04918 =
         0.05901    0.00802    0.00923    0.00854
AFIX  23
H4A   2    0.416271    0.341272    0.456842    11.00000   -1.20000
H4B   2    0.456587    0.415121    0.368822    11.00000   -1.20000
AFIX   0
C5    1    0.622885    0.386408    0.490783    11.00000    0.07201    0.04300 =
         0.05678   -0.00353    0.01703   -0.00904
AFIX  23
H5A   2    0.704772    0.363627    0.458756    11.00000   -1.20000
H5B   2    0.628616    0.456135    0.494280    11.00000   -1.20000
AFIX   0
C6    1    0.632413    0.347750    0.609379    11.00000    0.06986    0.06043 =
         0.04871   -0.01405    0.01271   -0.02435
AFIX  23
H6A   2    0.545748    0.365030    0.638378    11.00000   -1.20000
H6B   2    0.709750    0.380630    0.654613    11.00000   -1.20000
AFIX   0
C7    1    0.654922    0.239323    0.625174    11.00000    0.04293    0.06621 =
         0.03756    0.00436    0.00041   -0.01067
AFIX  23
H7A   2    0.730800    0.219938    0.584032    11.00000   -1.20000
H7B   2    0.687046    0.227410    0.703444    11.00000   -1.20000
AFIX   0
C8    1    0.528717    0.175268    0.589743    11.00000    0.03796    0.03971 =
         0.03652    0.00218    0.00255    0.00142
C9    1    0.450795    0.136414    0.668925    11.00000    0.03797    0.03781 =
         0.03392    0.00018    0.00181    0.00394
C10   1    0.337717    0.075023    0.633894    11.00000    0.04025    0.03829 =
         0.03478    0.00070    0.00423    0.00201
C11   1    0.302722    0.057619    0.519267    11.00000    0.04256    0.03743 =
         0.03728   -0.00097    0.00105   -0.00001
C12   1    0.259704    0.027452    0.711141    11.00000    0.04472    0.04905 =
         0.03740   -0.00375    0.00581   -0.00297
C13   1    0.146674   -0.010942    0.371440    11.00000    0.06234    0.06136 =
         0.04125   -0.00438   -0.00813   -0.01150
AFIX 137
H13A  2    0.066710   -0.053627    0.359608    11.00000   -1.50000
H13B  2    0.223549   -0.037653    0.337719    11.00000   -1.50000
H13C  2    0.120829    0.050535    0.338461    11.00000   -1.50000
AFIX   0
C14   1    0.485332    0.158567    0.790524    11.00000    0.03945    0.05161 =
         0.03484   -0.00345    0.00452   -0.00485
C15   1    0.555286    0.095668    0.864601    11.00000    0.05744    0.06744 =
         0.04037    0.00102    0.00235    0.00280
PART    1
AFIX  43
H15   2    0.578282    0.035643    0.838039    21.00000   -1.20000
AFIX   0
F1B   3    0.383992    0.309202    0.759824    21.00000    0.10891    0.07316 =
         0.05980    0.00582    0.00436    0.03990
PART    0
C16   1    0.594283    0.114367    0.975458    11.00000    0.06697    0.11262 =
         0.04017    0.01134   -0.00136   -0.00469
AFIX  43
H16   2    0.641801    0.068658    1.022753    11.00000   -1.20000
AFIX   0
C17   1    0.560485    0.203362    1.014217    11.00000    0.07965    0.12257 =
         0.04031   -0.02502    0.01124   -0.02932
AFIX  43
H17   2    0.585859    0.218581    1.089040    11.00000   -1.20000
AFIX   0
C18   1    0.490093    0.269563    0.943991    11.00000    0.08350    0.08000 =
         0.06088   -0.03085    0.02773   -0.02135
AFIX  43
H18   2    0.467255    0.329526    0.970815    11.00000   -1.20000
AFIX   0
C19   1    0.453211    0.247080    0.833506    11.00000    0.06120    0.06307 =
         0.05144   -0.01538    0.01894   -0.01007
PART    2
AFIX  43
H19   2    0.405284    0.292589    0.786164   -21.00000   -1.20000
AFIX   0
F1A   3    0.585718    0.008541    0.825251   -21.00000    0.10891    0.07316 =
         0.05980    0.00582    0.00436    0.03990
PART    0
N1    4    0.375213    0.093327    0.444153    11.00000    0.04819    0.04079 =
         0.03519   -0.00103    0.00347   -0.00028
N2    4    0.199468   -0.013106    0.771761    11.00000    0.06484    0.07567 =
         0.05007    0.00077    0.01609   -0.01468
O1    5    0.189886    0.000881    0.488717    11.00000    0.05534    0.05854 =
         0.03868   -0.00059   -0.00254   -0.01678
HKLF 4
REM  I P 21/n R = 0.06
REM R1 =  0.0553 for   2812 Fo > 4sig(Fo)  and  0.0670 for all   3475 data
REM    214 parameters refined using     10 restraints
END
WGHT      0.0677      0.8186
REM Highest difference peak  0.742,  deepest hole -0.598,  1-sigma level  0.041
Q1    1   0.3679  0.2844  0.7800  11.00000  0.05    0.74
Q2    1   0.5679  0.0688  0.8558  11.00000  0.05    0.24
Q3    1   0.3077  0.0718  0.5816  11.00000  0.05    0.17
Q4    1   0.5501  0.3586  0.4584  11.00000  0.05    0.16
Q5    1   0.4951  0.1772  0.5322  11.00000  0.05    0.15
Q6    1   0.6410  0.3567  0.5448  11.00000  0.05    0.15
Q7    1   0.4711  0.1755  0.6297  11.00000  0.05    0.15
Q8    1   0.5847  0.2037  0.6025  11.00000  0.05    0.15
Q9    1   0.3680  0.1228  0.6486  11.00000  0.05    0.15
Q10   1   0.5263  0.1704  0.4362  11.00000  0.05    0.14
Q11   1   0.5025  0.2154  0.9657  11.00000  0.05    0.14
Q12   1   0.4729  0.3057  0.3779  11.00000  0.05    0.13
Q13   1   0.3144  0.0398  0.6722  11.00000  0.05    0.13
Q14   1   0.6446  0.0324  1.0168  11.00000  0.05    0.12
Q15   1   0.7214 -0.0011  0.9995  11.00000  0.05    0.12
Q16   1   0.6146  0.1703  0.9813  11.00000  0.05    0.12
Q17   1   0.5198  0.1348  0.6337  11.00000  0.05    0.12
Q18   1   0.6266  0.1992  1.1025  11.00000  0.05    0.12
Q19   1   0.6580  0.0627  0.8419  11.00000  0.05    0.12
Q20   1   0.6752  0.0237  0.9961  11.00000  0.05    0.12
;