##############################################################################
#                                                                            #
# 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
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Dimethyl 3,3'-[(3-fluorophenyl)methylene]bis(1<i>H</i>-indole-2-carboxylate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H21 F N2 O4'
_chemical_formula_sum     'C27 H21 F N2 O4'
_chemical_formula_iupac     'C27 H21 F N2 O4'
_chemical_formula_weight     456.46
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.6980(19)
_cell_length_b     10.119(2)
_cell_length_c     12.875(3)
_cell_angle_alpha     89.86(3)
_cell_angle_beta     83.10(3)
_cell_angle_gamma     65.45(3)
_cell_volume     1139.4(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     13
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.331
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     476
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details
;
(North <i>et al.</i>,  1968)
;
_exptl_absorpt_correction_T_min     0.9719
_exptl_absorpt_correction_T_max     0.9905
_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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     \w/2\q
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4453
_diffrn_reflns_av_R_equivalents     0.0359
_diffrn_reflns_av_sigmaI/netI     0.0623
_diffrn_reflns_theta_min     1.60
_diffrn_reflns_theta_max     25.37
_diffrn_reflns_theta_full     25.37
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     1
_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     4183
_reflns_number_gt     2587
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1055
_refine_ls_R_factor_gt     0.0603
_refine_ls_wR_factor_gt     0.1429
_refine_ls_wR_factor_ref     0.1632
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.005
_refine_ls_number_reflns     4183
_refine_ls_number_parameters     307
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0850P)^2^+0.0000P] 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     0.723
_refine_diff_density_min     -0.248
_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'
    'F' 'F' 0.0171 0.0103
                         '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 (Enraf--Nonius, 1994)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1995)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 -0.1052(3) 0.5029(2) 0.13830(18) 0.0445(6) Uani d . 1 1 . .
    H H1A -0.1408 0.4496 0.1090 0.053 Uiso calc R 1 1 . .
    O O1 0.3009(2) 0.3113(2) 0.08820(18) 0.0586(6) Uani d . 1 1 . .
    C C1 0.2144(3) 0.5855(3) 0.2059(2) 0.0334(6) Uani d . 1 1 . .
    H H1B 0.2859 0.5329 0.1441 0.040 Uiso calc R 1 1 . .
    O O2 0.1188(3) 0.2409(2) 0.05471(17) 0.0555(6) Uani d . 1 1 . .
    N N2 0.1837(3) 0.9546(2) 0.14191(17) 0.0396(6) Uani d . 1 1 . .
    H H2A 0.1767 1.0211 0.0985 0.048 Uiso calc R 1 1 . .
    C C2 0.0646(3) 0.5803(3) 0.1908(2) 0.0341(6) Uani d . 1 1 . .
    O O3 0.2455(2) 0.6468(2) -0.02476(15) 0.0486(5) Uani d . 1 1 . .
    C C3 -0.0884(3) 0.6830(3) 0.2299(2) 0.0359(6) Uani d . 1 1 . .
    O O4 0.1821(3) 0.8813(2) -0.05567(15) 0.0529(6) Uani d . 1 1 . .
    C C4 -0.1512(3) 0.8120(3) 0.2943(2) 0.0439(7) Uani d . 1 1 . .
    H H4A -0.0880 0.8485 0.3207 0.053 Uiso calc R 1 1 . .
    F F 0.6593(3) 0.3395(3) 0.38335(19) 0.1028(8) Uani d U 1 1 . .
    C C5 -0.3065(4) 0.8827(3) 0.3173(2) 0.0522(8) Uani d . 1 1 . .
    H H5B -0.3483 0.9676 0.3601 0.063 Uiso calc R 1 1 . .
    C C6 -0.4039(4) 0.8314(3) 0.2787(3) 0.0545(8) Uani d . 1 1 . .
    H H6A -0.5090 0.8841 0.2951 0.065 Uiso calc R 1 1 . .
    C C7 -0.3497(4) 0.7059(3) 0.2175(3) 0.0518(8) Uani d . 1 1 . .
    H H7A -0.4154 0.6715 0.1924 0.062 Uiso calc R 1 1 . .
    C C8 -0.1906(3) 0.6313(3) 0.1940(2) 0.0394(7) Uani d . 1 1 . .
    C C9 0.0469(3) 0.4723(3) 0.1365(2) 0.0368(6) Uani d . 1 1 . .
    C C10 0.1559(4) 0.3315(3) 0.0883(2) 0.0416(7) Uani d . 1 1 . .
    C C11 0.4154(4) 0.1713(4) 0.0498(3) 0.0767(11) Uani d . 1 1 . .
    H H11A 0.5149 0.1686 0.0529 0.115 Uiso calc R 1 1 . .
    H H11B 0.4049 0.1537 -0.0215 0.115 Uiso calc R 1 1 . .
    H H11C 0.4031 0.0977 0.0921 0.115 Uiso calc R 1 1 . .
    C C12 0.2062(3) 0.7399(3) 0.2047(2) 0.0312(6) Uani d . 1 1 . .
    C C13 0.1975(3) 0.8347(3) 0.2903(2) 0.0331(6) Uani d . 1 1 . .
    C C14 0.2017(3) 0.8230(3) 0.3985(2) 0.0416(7) Uani d . 1 1 . .
    H H14A 0.2120 0.7368 0.4295 0.050 Uiso calc R 1 1 . .
    C C15 0.1906(4) 0.9398(3) 0.4581(2) 0.0517(8) Uani d . 1 1 . .
    H H15A 0.1949 0.9317 0.5297 0.062 Uiso calc R 1 1 . .
    C C16 0.1728(4) 1.0709(3) 0.4134(3) 0.0547(9) Uani d . 1 1 . .
    H H16A 0.1632 1.1488 0.4563 0.066 Uiso calc R 1 1 . .
    C C17 0.1692(4) 1.0876(3) 0.3093(2) 0.0489(8) Uani d . 1 1 . .
    H H17A 0.1586 1.1748 0.2799 0.059 Uiso calc R 1 1 . .
    C C18 0.1821(3) 0.9681(3) 0.2474(2) 0.0373(7) Uani d . 1 1 . .
    C C19 0.1986(3) 0.8161(3) 0.1163(2) 0.0339(6) Uani d . 1 1 . .
    C C20 0.2100(3) 0.7701(3) 0.0063(2) 0.0376(7) Uani d . 1 1 . .
    C C21 0.1995(4) 0.8471(4) -0.1662(2) 0.0666(10) Uani d . 1 1 . .
    H H21A 0.1770 0.9343 -0.2036 0.100 Uiso calc R 1 1 . .
    H H21B 0.1303 0.8053 -0.1797 0.100 Uiso calc R 1 1 . .
    H H21C 0.3027 0.7788 -0.1891 0.100 Uiso calc R 1 1 . .
    C C22 0.2846(3) 0.5040(3) 0.2992(2) 0.0367(7) Uani d . 1 1 . .
    C C23 0.4402(3) 0.4571(3) 0.3005(2) 0.0449(7) Uani d . 1 1 . .
    H H23A 0.5000 0.4746 0.2449 0.054 Uiso calc R 1 1 . .
    C C24 0.5055(4) 0.3846(4) 0.3845(3) 0.0548(8) Uani d U 1 1 . .
    C C25 0.4234(4) 0.3559(4) 0.4673(3) 0.0629(10) Uani d . 1 1 . .
    H H25A 0.4706 0.3062 0.5232 0.076 Uiso calc R 1 1 . .
    C C26 0.2694(4) 0.4020(4) 0.4664(3) 0.0639(10) Uani d . 1 1 . .
    H H26A 0.2105 0.3844 0.5226 0.077 Uiso calc R 1 1 . .
    C C27 0.2007(4) 0.4745(3) 0.3822(2) 0.0491(8) Uani d . 1 1 . .
    H H27A 0.0963 0.5036 0.3820 0.059 Uiso calc R 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
    N1 0.0524(17) 0.0385(13) 0.0546(15) -0.0295(12) -0.0120(12) -0.0062(11)
    O1 0.0498(14) 0.0351(11) 0.0876(17) -0.0160(10) -0.0029(12) -0.0176(11)
    C1 0.0389(16) 0.0255(13) 0.0378(15) -0.0145(12) -0.0079(12) -0.0016(11)
    O2 0.0730(16) 0.0339(11) 0.0677(14) -0.0277(11) -0.0187(12) -0.0071(10)
    N2 0.0548(16) 0.0283(11) 0.0403(14) -0.0212(11) -0.0092(11) 0.0015(10)
    C2 0.0378(16) 0.0297(13) 0.0389(15) -0.0173(12) -0.0088(12) -0.0001(11)
    O3 0.0655(15) 0.0392(11) 0.0468(12) -0.0257(10) -0.0143(10) -0.0053(9)
    C3 0.0392(16) 0.0349(14) 0.0392(15) -0.0200(13) -0.0086(12) 0.0029(12)
    O4 0.0744(16) 0.0425(11) 0.0401(12) -0.0228(11) -0.0075(10) 0.0044(9)
    C4 0.0446(19) 0.0390(16) 0.0507(18) -0.0197(14) -0.0065(14) -0.0108(14)
    F 0.0659(15) 0.131(2) 0.0963(18) -0.0211(15) -0.0317(13) 0.0148(15)
    C5 0.0440(19) 0.0439(17) 0.063(2) -0.0142(15) 0.0002(15) -0.0118(15)
    C6 0.0383(19) 0.055(2) 0.067(2) -0.0171(16) -0.0064(16) 0.0020(17)
    C7 0.0432(19) 0.0553(19) 0.067(2) -0.0292(16) -0.0115(16) 0.0039(16)
    C8 0.0422(17) 0.0407(16) 0.0422(16) -0.0233(14) -0.0094(13) 0.0029(13)
    C9 0.0433(17) 0.0332(14) 0.0400(16) -0.0205(13) -0.0111(13) 0.0015(12)
    C10 0.057(2) 0.0320(14) 0.0411(16) -0.0232(14) -0.0096(14) 0.0026(12)
    C11 0.058(2) 0.047(2) 0.108(3) -0.0091(18) 0.003(2) -0.020(2)
    C12 0.0289(14) 0.0286(13) 0.0399(15) -0.0149(11) -0.0085(12) -0.0012(11)
    C13 0.0305(15) 0.0307(14) 0.0413(16) -0.0156(12) -0.0066(12) -0.0027(12)
    C14 0.0461(18) 0.0370(15) 0.0437(17) -0.0187(14) -0.0076(13) 0.0002(13)
    C15 0.064(2) 0.0522(19) 0.0421(17) -0.0270(17) -0.0089(15) -0.0080(15)
    C16 0.067(2) 0.0413(17) 0.055(2) -0.0216(16) -0.0093(16) -0.0156(15)
    C17 0.056(2) 0.0346(15) 0.058(2) -0.0204(15) -0.0095(15) -0.0068(14)
    C18 0.0351(16) 0.0317(14) 0.0451(17) -0.0133(12) -0.0080(13) -0.0043(12)
    C19 0.0376(16) 0.0297(13) 0.0384(15) -0.0174(12) -0.0070(12) -0.0028(12)
    C20 0.0383(17) 0.0363(15) 0.0414(16) -0.0180(13) -0.0078(13) -0.0015(13)
    C21 0.088(3) 0.069(2) 0.0409(19) -0.031(2) -0.0089(18) 0.0063(16)
    C22 0.0415(17) 0.0274(13) 0.0429(16) -0.0155(12) -0.0075(13) -0.0046(12)
    C23 0.0471(19) 0.0438(16) 0.0451(18) -0.0196(14) -0.0083(14) 0.0030(14)
    C24 0.0472(19) 0.0567(19) 0.054(2) -0.0121(16) -0.0195(16) 0.0022(16)
    C25 0.078(3) 0.062(2) 0.048(2) -0.023(2) -0.0242(19) 0.0152(16)
    C26 0.075(3) 0.072(2) 0.052(2) -0.037(2) -0.0126(18) 0.0107(18)
    C27 0.0469(19) 0.0564(19) 0.0498(19) -0.0263(16) -0.0105(15) 0.0107(15)
_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
    N1 C8 . 1.362(3) ?
    N1 C9 . 1.373(4) ?
    N1 H1A . 0.8600 ?
    O1 C10 . 1.333(4) ?
    O1 C11 . 1.431(4) ?
    C1 C2 . 1.511(4) ?
    C1 C22 . 1.520(4) ?
    C1 C12 . 1.532(3) ?
    C1 H1B . 0.9800 ?
    O2 C10 . 1.213(3) ?
    N2 C18 . 1.363(3) ?
    N2 C19 . 1.385(3) ?
    N2 H2A . 0.8600 ?
    C2 C9 . 1.379(3) ?
    C2 C3 . 1.440(4) ?
    O3 C20 . 1.203(3) ?
    C3 C4 . 1.409(4) ?
    C3 C8 . 1.419(4) ?
    O4 C20 . 1.330(3) ?
    O4 C21 . 1.439(3) ?
    C4 C5 . 1.366(4) ?
    C4 H4A . 0.9300 ?
    F C24 . 1.364(4) ?
    C5 C6 . 1.389(4) ?
    C5 H5B . 0.9300 ?
    C6 C7 . 1.364(4) ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.401(4) ?
    C7 H7A . 0.9300 ?
    C9 C10 . 1.458(4) ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C19 . 1.365(4) ?
    C12 C13 . 1.435(3) ?
    C13 C14 . 1.402(4) ?
    C13 C18 . 1.413(4) ?
    C14 C15 . 1.370(4) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.396(4) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.353(4) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.403(4) ?
    C17 H17A . 0.9300 ?
    C19 C20 . 1.469(4) ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
    C22 C27 . 1.373(4) ?
    C22 C23 . 1.383(4) ?
    C23 C24 . 1.372(4) ?
    C23 H23A . 0.9300 ?
    C24 C25 . 1.357(5) ?
    C25 C26 . 1.370(5) ?
    C25 H25A . 0.9300 ?
    C26 C27 . 1.385(4) ?
    C26 H26A . 0.9300 ?
    C27 H27A . 0.9300 ?
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
    C8 N1 C9 . . 109.0(2) ?
    C8 N1 H1A . . 125.5 ?
    C9 N1 H1A . . 125.5 ?
    C10 O1 C11 . . 116.3(2) ?
    C2 C1 C22 . . 113.7(2) ?
    C2 C1 C12 . . 112.9(2) ?
    C22 C1 C12 . . 112.7(2) ?
    C2 C1 H1B . . 105.5 ?
    C22 C1 H1B . . 105.5 ?
    C12 C1 H1B . . 105.5 ?
    C18 N2 C19 . . 108.7(2) ?
    C18 N2 H2A . . 125.7 ?
    C19 N2 H2A . . 125.7 ?
    C9 C2 C3 . . 105.3(2) ?
    C9 C2 C1 . . 126.3(2) ?
    C3 C2 C1 . . 128.5(2) ?
    C4 C3 C8 . . 117.9(3) ?
    C4 C3 C2 . . 134.8(3) ?
    C8 C3 C2 . . 107.3(2) ?
    C20 O4 C21 . . 116.2(2) ?
    C5 C4 C3 . . 118.9(3) ?
    C5 C4 H4A . . 120.6 ?
    C3 C4 H4A . . 120.6 ?
    C4 C5 C6 . . 121.9(3) ?
    C4 C5 H5B . . 119.0 ?
    C6 C5 H5B . . 119.0 ?
    C7 C6 C5 . . 121.8(3) ?
    C7 C6 H6A . . 119.1 ?
    C5 C6 H6A . . 119.1 ?
    C6 C7 C8 . . 117.0(3) ?
    C6 C7 H7A . . 121.5 ?
    C8 C7 H7A . . 121.5 ?
    N1 C8 C7 . . 129.8(3) ?
    N1 C8 C3 . . 107.7(2) ?
    C7 C8 C3 . . 122.5(3) ?
    N1 C9 C2 . . 110.7(2) ?
    N1 C9 C10 . . 116.5(2) ?
    C2 C9 C10 . . 132.5(3) ?
    O2 C10 O1 . . 123.6(3) ?
    O2 C10 C9 . . 123.6(3) ?
    O1 C10 C9 . . 112.8(2) ?
    O1 C11 H11A . . 109.5 ?
    O1 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    O1 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C19 C12 C13 . . 106.8(2) ?
    C19 C12 C1 . . 123.7(2) ?
    C13 C12 C1 . . 129.4(2) ?
    C14 C13 C18 . . 118.0(2) ?
    C14 C13 C12 . . 135.4(2) ?
    C18 C13 C12 . . 106.6(2) ?
    C15 C14 C13 . . 119.3(3) ?
    C15 C14 H14A . . 120.4 ?
    C13 C14 H14A . . 120.4 ?
    C14 C15 C16 . . 121.3(3) ?
    C14 C15 H15A . . 119.4 ?
    C16 C15 H15A . . 119.4 ?
    C17 C16 C15 . . 121.8(3) ?
    C17 C16 H16A . . 119.1 ?
    C15 C16 H16A . . 119.1 ?
    C16 C17 C18 . . 117.3(3) ?
    C16 C17 H17A . . 121.3 ?
    C18 C17 H17A . . 121.3 ?
    N2 C18 C17 . . 129.5(3) ?
    N2 C18 C13 . . 108.2(2) ?
    C17 C18 C13 . . 122.3(3) ?
    C12 C19 N2 . . 109.8(2) ?
    C12 C19 C20 . . 130.1(2) ?
    N2 C19 C20 . . 120.1(2) ?
    O3 C20 O4 . . 124.0(2) ?
    O3 C20 C19 . . 124.5(3) ?
    O4 C20 C19 . . 111.4(2) ?
    O4 C21 H21A . . 109.5 ?
    O4 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O4 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    C27 C22 C23 . . 118.4(3) ?
    C27 C22 C1 . . 123.0(3) ?
    C23 C22 C1 . . 118.5(3) ?
    C24 C23 C22 . . 119.4(3) ?
    C24 C23 H23A . . 120.3 ?
    C22 C23 H23A . . 120.3 ?
    C25 C24 F . . 119.4(3) ?
    C25 C24 C23 . . 122.6(3) ?
    F C24 C23 . . 118.0(3) ?
    C24 C25 C26 . . 118.2(3) ?
    C24 C25 H25A . . 120.9 ?
    C26 C25 H25A . . 120.9 ?
    C25 C26 C27 . . 120.4(3) ?
    C25 C26 H26A . . 119.8 ?
    C27 C26 H26A . . 119.8 ?
    C22 C27 C26 . . 121.0(3) ?
    C22 C27 H27A . . 119.5 ?
    C26 C27 H27A . . 119.5 ?
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
    C22 C1 C2 C9 . . . . -86.0(3) ?
    C12 C1 C2 C9 . . . . 143.9(3) ?
    C22 C1 C2 C3 . . . . 93.1(3) ?
    C12 C1 C2 C3 . . . . -37.0(4) ?
    C9 C2 C3 C4 . . . . 176.4(3) ?
    C1 C2 C3 C4 . . . . -2.8(5) ?
    C9 C2 C3 C8 . . . . -1.3(3) ?
    C1 C2 C3 C8 . . . . 179.4(2) ?
    C8 C3 C4 C5 . . . . -1.4(4) ?
    C2 C3 C4 C5 . . . . -178.9(3) ?
    C3 C4 C5 C6 . . . . -0.3(5) ?
    C4 C5 C6 C7 . . . . 1.4(5) ?
    C5 C6 C7 C8 . . . . -0.7(5) ?
    C9 N1 C8 C7 . . . . -179.6(3) ?
    C9 N1 C8 C3 . . . . -0.7(3) ?
    C6 C7 C8 N1 . . . . 177.7(3) ?
    C6 C7 C8 C3 . . . . -1.1(4) ?
    C4 C3 C8 N1 . . . . -176.9(2) ?
    C2 C3 C8 N1 . . . . 1.3(3) ?
    C4 C3 C8 C7 . . . . 2.1(4) ?
    C2 C3 C8 C7 . . . . -179.7(3) ?
    C8 N1 C9 C2 . . . . -0.2(3) ?
    C8 N1 C9 C10 . . . . 174.5(2) ?
    C3 C2 C9 N1 . . . . 0.9(3) ?
    C1 C2 C9 N1 . . . . -179.8(2) ?
    C3 C2 C9 C10 . . . . -172.5(3) ?
    C1 C2 C9 C10 . . . . 6.7(5) ?
    C11 O1 C10 O2 . . . . -2.7(4) ?
    C11 O1 C10 C9 . . . . 175.3(3) ?
    N1 C9 C10 O2 . . . . -3.0(4) ?
    C2 C9 C10 O2 . . . . 170.1(3) ?
    N1 C9 C10 O1 . . . . 179.0(2) ?
    C2 C9 C10 O1 . . . . -7.9(4) ?
    C2 C1 C12 C19 . . . . -72.7(3) ?
    C22 C1 C12 C19 . . . . 156.8(2) ?
    C2 C1 C12 C13 . . . . 104.0(3) ?
    C22 C1 C12 C13 . . . . -26.5(4) ?
    C19 C12 C13 C14 . . . . -178.6(3) ?
    C1 C12 C13 C14 . . . . 4.3(5) ?
    C19 C12 C13 C18 . . . . 1.0(3) ?
    C1 C12 C13 C18 . . . . -176.2(3) ?
    C18 C13 C14 C15 . . . . 0.1(4) ?
    C12 C13 C14 C15 . . . . 179.7(3) ?
    C13 C14 C15 C16 . . . . 1.0(5) ?
    C14 C15 C16 C17 . . . . -1.5(5) ?
    C15 C16 C17 C18 . . . . 0.8(5) ?
    C19 N2 C18 C17 . . . . 180.0(3) ?
    C19 N2 C18 C13 . . . . 0.5(3) ?
    C16 C17 C18 N2 . . . . -179.1(3) ?
    C16 C17 C18 C13 . . . . 0.3(4) ?
    C14 C13 C18 N2 . . . . 178.7(2) ?
    C12 C13 C18 N2 . . . . -0.9(3) ?
    C14 C13 C18 C17 . . . . -0.8(4) ?
    C12 C13 C18 C17 . . . . 179.6(3) ?
    C13 C12 C19 N2 . . . . -0.7(3) ?
    C1 C12 C19 N2 . . . . 176.7(2) ?
    C13 C12 C19 C20 . . . . 176.5(3) ?
    C1 C12 C19 C20 . . . . -6.1(4) ?
    C18 N2 C19 C12 . . . . 0.1(3) ?
    C18 N2 C19 C20 . . . . -177.4(2) ?
    C21 O4 C20 O3 . . . . -1.2(4) ?
    C21 O4 C20 C19 . . . . 176.3(3) ?
    C12 C19 C20 O3 . . . . -8.5(5) ?
    N2 C19 C20 O3 . . . . 168.5(3) ?
    C12 C19 C20 O4 . . . . 174.0(3) ?
    N2 C19 C20 O4 . . . . -9.0(4) ?
    C2 C1 C22 C27 . . . . -22.3(4) ?
    C12 C1 C22 C27 . . . . 107.9(3) ?
    C2 C1 C22 C23 . . . . 157.6(2) ?
    C12 C1 C22 C23 . . . . -72.3(3) ?
    C27 C22 C23 C24 . . . . -0.8(4) ?
    C1 C22 C23 C24 . . . . 179.4(2) ?
    C22 C23 C24 C25 . . . . 0.3(5) ?
    C22 C23 C24 F . . . . 179.9(3) ?
    F C24 C25 C26 . . . . -179.8(3) ?
    C23 C24 C25 C26 . . . . -0.2(5) ?
    C24 C25 C26 C27 . . . . 0.7(5) ?
    C23 C22 C27 C26 . . . . 1.2(4) ?
    C1 C22 C27 C26 . . . . -178.9(3) ?
    C25 C26 C27 C22 . . . . -1.2(5) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N1 H1A O3 2_565 0.86 2.06 2.913(3) 170
    N2 H2A O2 1_565 0.86 2.15 2.948(3) 155
    C6 H6A Cg4 1_455 0.93 2.75 3.645(4) 162
data_global
_journal_date_recd_electronic     2014-11-24
_journal_date_accepted     2014-11-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue     12
_journal_page_first     593
_journal_page_last     595
_journal_paper_category     GO
_journal_paper_doi     10.1107/S1600536814025756
_journal_coeditor_code     XU5830
_publ_contact_author_name     'Sun, Hong-shun'
_publ_contact_author_address
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Geguan Road No.265 Nanjing
Nanjing 210048
People's Republic of China
;
_publ_contact_author_email
;
njutshs@126.com
;
_publ_contact_author_fax     '86 25 58370621'
_publ_contact_author_phone     '86 25 58370534'
_publ_section_title
;
Crystal structure of dimethyl
3,3'-[(3-fluorophenyl)methylene]bis(1<i>H</i>-indole-2-carboxylate)
;
loop_
    _publ_author_name
    _publ_author_address
    'Lu, Xin-Hua'
;
Department of Applied Chemistry
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
    'Sun, Hong-Shun'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
    'Hu, Jin'
;
Department of Applied Chemistry
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
_publ_section_synopsis
;
In the title compound, the two indole ring systems are approximately
perpendicular to one another, making a dihedral angle of 87.8(5)\%. In the
crystal, pairs of N---H...O hydrogen bonds link the molecules into the
inversion dimers, which are further linked by N---H...O hydrogen bonds into
supramolecular chains propagating along the <i>b-</i>axis direction.
;