##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, 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     SHELXL97
_chemical_name_systematic
;
3-Chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
_chemical_name_common
;
3-Chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
_chemical_formula_moiety     'C12 H11 Cl N2'
_chemical_formula_sum     'C12 H11 Cl N2'
_chemical_formula_iupac     'C12 H11 Cl N2'
_chemical_formula_weight     218.68
_chemical_melting_point     362.6
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     23.722(15)
_cell_length_b     5.720(4)
_cell_length_c     16.868(11)
_cell_angle_alpha     90.00
_cell_angle_beta     98.404(10)
_cell_angle_gamma     90.00
_cell_volume     2264(3)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     3.20
_cell_measurement_theta_max     26.22
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.283
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     912
_exptl_absorpt_coefficient_mu     0.305
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.8964
_exptl_absorpt_correction_T_max     0.9405
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5682
_diffrn_reflns_av_R_equivalents     0.0442
_diffrn_reflns_av_sigmaI/netI     0.0495
_diffrn_reflns_theta_min     3.20
_diffrn_reflns_theta_max     26.22
_diffrn_reflns_theta_full     26.22
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full     0.983
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     29
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     2235
_reflns_number_gt     1611
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0597
_refine_ls_R_factor_gt     0.0419
_refine_ls_wR_factor_gt     0.1082
_refine_ls_wR_factor_ref     0.1195
_refine_ls_goodness_of_fit_ref     1.008
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     2235
_refine_ls_number_parameters     145
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0550P)²+0.7500P] 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     0.189
_refine_diff_density_min     -0.191
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0035(8)
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.47791(2) 0.67469(13) 0.35356(4) 0.0865(3) Uani d . 1 1 . .
    N N1 0.16869(6) 0.7513(3) 0.40993(10) 0.0563(4) Uani d D 1 1 . .
    H H1 0.1925(9) 0.813(4) 0.4468(11) 0.068 Uiso d PD 0.85(3) 1 . .
    N N2 0.27532(6) 0.5367(3) 0.41718(10) 0.0549(4) Uani d D 1 1 . .
    H H2A 0.270(6) 0.61(2) 0.460(5) 0.066 Uiso d PD 0.15(3) 1 . .
    C C1 0.11410(8) 0.8304(4) 0.38903(13) 0.0688(6) Uani d . 1 1 . .
    H H1A 0.0976 0.9554 0.4124 0.083 Uiso calc R 1 1 . .
    C C2 0.08828(9) 0.6952(5) 0.32843(14) 0.0842(7) Uani d . 1 1 . .
    H H2 0.0511 0.7117 0.3027 0.101 Uiso calc R 1 1 . .
    C C3 0.12771(9) 0.5252(4) 0.31127(13) 0.0782(7) Uani d . 1 1 . .
    H H3 0.1212 0.4086 0.2726 0.094 Uiso calc R 1 1 . .
    C C4 0.17798(7) 0.5635(3) 0.36246(10) 0.0542(5) Uani d . 1 1 . .
    C C5 0.23386(7) 0.4508(3) 0.36766(10) 0.0509(4) Uani d . 1 1 . .
    C C6 0.23902(10) 0.2473(4) 0.31262(13) 0.0696(6) Uani d . 1 1 . .
    H H6A 0.2657 0.2850 0.2769 0.104 Uiso calc PR 0.53(3) 1 . .
    H H6B 0.2025 0.2146 0.2820 0.104 Uiso calc PR 0.53(3) 1 . .
    H H6C 0.2522 0.1123 0.3438 0.104 Uiso calc PR 0.53(3) 1 . .
    H H6E 0.2145 0.1230 0.3249 0.104 Uiso calc PR 0.47(3) 1 . .
    H H6D 0.2778 0.1933 0.3198 0.104 Uiso calc PR 0.47(3) 1 . .
    H H6F 0.2281 0.2957 0.2580 0.104 Uiso calc PR 0.47(3) 1 . .
    C C7 0.33193(7) 0.4440(3) 0.42002(10) 0.0518(4) Uani d . 1 1 . .
    C C8 0.34820(9) 0.2336(4) 0.45754(13) 0.0674(6) Uani d . 1 1 . .
    H H8 0.3215 0.1411 0.4781 0.081 Uiso calc R 1 1 . .
    C C9 0.40503(10) 0.1618(4) 0.46411(14) 0.0763(6) Uani d . 1 1 . .
    H H9 0.4160 0.0225 0.4904 0.092 Uiso calc R 1 1 . .
    C C10 0.44537(9) 0.2937(4) 0.43234(13) 0.0708(6) Uani d . 1 1 . .
    H H10 0.4830 0.2438 0.4366 0.085 Uiso calc R 1 1 . .
    C C11 0.42814(8) 0.5022(4) 0.39403(11) 0.0591(5) Uani d . 1 1 . .
    C C12 0.37214(7) 0.5807(3) 0.38867(10) 0.0535(4) Uani d . 1 1 . .
    H H12 0.3616 0.7232 0.3644 0.064 Uiso calc R 1 1 . .
_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.
;
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
    Cl1 C11 . 1.752(2) ?
    N1 C1 . 1.369(3) y
    N1 C4 . 1.377(3) y
    N1 H1 . 0.852(10) ?
    N2 C5 . 1.291(2) y
    N2 C7 . 1.438(2) y
    N2 H2A . 0.861(10) y
    C1 C2 . 1.355(3) y
    C1 H1A . 0.9300 ?
    C2 C3 . 1.408(3) y
    C2 H2 . 0.9300 ?
    C3 C4 . 1.384(3) y
    C3 H3 . 0.9300 ?
    C4 C5 . 1.465(3) y
    C5 C6 . 1.505(3) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C6 H6E . 0.9600 ?
    C6 H6D . 0.9600 ?
    C6 H6F . 0.9600 ?
    C7 C8 . 1.388(3) ?
    C7 C12 . 1.396(3) ?
    C8 C9 . 1.398(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.386(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.390(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.392(2) ?
    C12 H12 . 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
    C1 N1 C4 . . 109.51(17) y
    C1 N1 H1 . . 123.5(17) ?
    C4 N1 H1 . . 127.0(17) ?
    C5 N2 C7 . . 120.04(16) ?
    C5 N2 H2A . . 122(9) ?
    C7 N2 H2A . . 114(9) ?
    C2 C1 N1 . . 108.18(19) y
    C2 C1 H1A . . 125.9 ?
    N1 C1 H1A . . 125.9 ?
    C1 C2 C3 . . 107.98(19) y
    C1 C2 H2 . . 126.0 ?
    C3 C2 H2 . . 126.0 ?
    C4 C3 C2 . . 107.5(2) y
    C4 C3 H3 . . 126.3 ?
    C2 C3 H3 . . 126.3 ?
    N1 C4 C3 . . 106.84(17) y
    N1 C4 C5 . . 121.92(15) y
    C3 C4 C5 . . 131.12(19) ?
    N2 C5 C4 . . 117.94(17) y
    N2 C5 C6 . . 124.79(17) ?
    C4 C5 C6 . . 117.24(16) ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C5 C6 H6E . . 109.5 ?
    H6A C6 H6E . . 141.1 ?
    H6B C6 H6E . . 56.3 ?
    H6C C6 H6E . . 56.3 ?
    C5 C6 H6D . . 109.5 ?
    H6A C6 H6D . . 56.3 ?
    H6B C6 H6D . . 141.1 ?
    H6C C6 H6D . . 56.3 ?
    H6E C6 H6D . . 109.5 ?
    C5 C6 H6F . . 109.5 ?
    H6A C6 H6F . . 56.3 ?
    H6B C6 H6F . . 56.3 ?
    H6C C6 H6F . . 141.1 ?
    H6E C6 H6F . . 109.5 ?
    H6D C6 H6F . . 109.5 ?
    C8 C7 C12 . . 119.91(17) ?
    C8 C7 N2 . . 122.08(17) ?
    C12 C7 N2 . . 117.86(17) ?
    C7 C8 C9 . . 119.4(2) ?
    C7 C8 H8 . . 120.3 ?
    C9 C8 H8 . . 120.3 ?
    C10 C9 C8 . . 121.4(2) ?
    C10 C9 H9 . . 119.3 ?
    C8 C9 H9 . . 119.3 ?
    C9 C10 C11 . . 118.30(19) ?
    C9 C10 H10 . . 120.8 ?
    C11 C10 H10 . . 120.8 ?
    C10 C11 C12 . . 121.34(19) ?
    C10 C11 Cl1 . . 119.70(15) ?
    C12 C11 Cl1 . . 118.94(16) ?
    C11 C12 C7 . . 119.53(18) ?
    C11 C12 H12 . . 120.2 ?
    C7 C12 H12 . . 120.2 ?
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 . . . . -0.1(3) ?
    N1 C1 C2 C3 . . . . 0.5(3) ?
    C1 C2 C3 C4 . . . . -0.6(3) ?
    C1 N1 C4 C3 . . . . -0.3(2) ?
    C1 N1 C4 C5 . . . . 176.12(17) ?
    C2 C3 C4 N1 . . . . 0.6(3) ?
    C2 C3 C4 C5 . . . . -175.4(2) ?
    C7 N2 C5 C4 . . . . -175.15(15) ?
    C7 N2 C5 C6 . . . . 2.8(3) ?
    N1 C4 C5 N2 . . . . -1.7(3) ?
    C3 C4 C5 N2 . . . . 173.7(2) ?
    N1 C4 C5 C6 . . . . -179.83(18) ?
    C3 C4 C5 C6 . . . . -4.4(3) ?
    C5 N2 C7 C8 . . . . -76.9(2) y
    C5 N2 C7 C12 . . . . 107.7(2) ?
    C12 C7 C8 C9 . . . . 0.5(3) ?
    N2 C7 C8 C9 . . . . -174.77(19) ?
    C7 C8 C9 C10 . . . . -1.5(3) ?
    C8 C9 C10 C11 . . . . 0.6(3) ?
    C9 C10 C11 C12 . . . . 1.2(3) ?
    C9 C10 C11 Cl1 . . . . 179.66(17) ?
    C10 C11 C12 C7 . . . . -2.1(3) ?
    Cl1 C11 C12 C7 . . . . 179.41(13) ?
    C8 C7 C12 C11 . . . . 1.2(3) ?
    N2 C7 C12 C11 . . . . 176.72(16) ?
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 N2 7_566 0.852(10) 2.465(14) 3.257(3) 155(2)
    N2 H2A N1 7_566 0.861(10) 2.58(9) 3.257(3) 136(11)
    C1 H1A Cg1 7_566 0.93 2.88 3.568(2) 132.0
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
4-Chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
_chemical_name_common
;
4-Chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
_chemical_formula_moiety     'C12 H11 Cl N2'
_chemical_formula_sum     'C12 H11 Cl N2'
_chemical_formula_iupac     'C12 H11 Cl N2'
_chemical_formula_weight     218.68
_chemical_melting_point     406.0
_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     13.323(3)
_cell_length_b     9.802(2)
_cell_length_c     9.107(2)
_cell_angle_alpha     90.00
_cell_angle_beta     109.212(4)
_cell_angle_gamma     90.00
_cell_volume     1123.1(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     3.15
_cell_measurement_theta_max     26.37
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.37
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.293
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     456
_exptl_absorpt_coefficient_mu     0.307
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2008)'
_exptl_absorpt_correction_T_min     0.8951
_exptl_absorpt_correction_T_max     0.9542
_exptl_special_details     ?
_diffrn_ambient_temperature     296(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 APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6016
_diffrn_reflns_av_R_equivalents     0.0311
_diffrn_reflns_av_sigmaI/netI     0.0325
_diffrn_reflns_theta_min     3.15
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 >
σ(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.
;
_reflns_number_total     2273
_reflns_number_gt     1701
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0642
_refine_ls_R_factor_gt     0.0472
_refine_ls_wR_factor_gt     0.1088
_refine_ls_wR_factor_ref     0.1189
_refine_ls_goodness_of_fit_ref     1.001
_refine_ls_restrained_S_all     1.001
_refine_ls_number_reflns     2273
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0380P)²+0.5000P] 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     0.308
_refine_diff_density_min     -0.375
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.084(5)
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'publCIF (Westrip, 2010)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.00330(5) 0.16504(11) 0.14277(11) 0.1178(4) Uani d . 1 1 . .
    N N1 0.65655(12) 0.04155(17) 0.16365(18) 0.0513(4) Uani d D 1 1 . .
    H H1 0.6113(13) 0.007(2) 0.0813(16) 0.062 Uiso d D 1 1 . .
    N N2 0.44650(12) 0.08102(17) 0.16294(18) 0.0541(4) Uani d . 1 1 . .
    C C1 0.76260(15) 0.0441(2) 0.1946(2) 0.0616(6) Uani d . 1 1 . .
    H H1A 0.7987 0.0081 0.1318 0.074 Uiso calc R 1 1 . .
    C C2 0.80796(17) 0.1080(2) 0.3330(3) 0.0686(6) Uani d . 1 1 . .
    H H2 0.8802 0.1235 0.3819 0.082 Uiso calc R 1 1 . .
    C C3 0.72636(17) 0.1458(2) 0.3875(3) 0.0645(6) Uani d . 1 1 . .
    H H3 0.7343 0.1915 0.4802 0.077 Uiso calc R 1 1 . .
    C C4 0.63166(15) 0.10419(19) 0.2812(2) 0.0495(5) Uani d . 1 1 . .
    C C5 0.52395(15) 0.12363(19) 0.2789(2) 0.0501(5) Uani d . 1 1 . .
    C C6 0.50966(19) 0.1964(3) 0.4156(3) 0.0790(7) Uani d . 1 1 . .
    H H6A 0.4391 0.2335 0.3868 0.118 Uiso calc PR 0.42(3) 1 . .
    H H6B 0.5607 0.2689 0.4476 0.118 Uiso calc PR 0.42(3) 1 . .
    H H6C 0.5200 0.1332 0.4999 0.118 Uiso calc PR 0.42(3) 1 . .
    H H6D 0.5741 0.1903 0.5027 0.118 Uiso calc PR 0.58(3) 1 . .
    H H6E 0.4526 0.1548 0.4419 0.118 Uiso calc PR 0.58(3) 1 . .
    H H6F 0.4932 0.2905 0.3896 0.118 Uiso calc PR 0.58(3) 1 . .
    C C7 0.34104(15) 0.1035(2) 0.1626(2) 0.0530(5) Uani d . 1 1 . .
    C C8 0.28700(18) 0.2205(2) 0.0996(3) 0.0684(6) Uani d . 1 1 . .
    H H8 0.3210 0.2877 0.0614 0.082 Uiso calc R 1 1 . .
    C C9 0.18295(19) 0.2391(3) 0.0924(3) 0.0745(7) Uani d . 1 1 . .
    H H9 0.1470 0.3186 0.0497 0.089 Uiso calc R 1 1 . .
    C C10 0.13327(17) 0.1407(3) 0.1481(3) 0.0713(6) Uani d . 1 1 . .
    C C11 0.18439(19) 0.0230(3) 0.2082(3) 0.0798(7) Uani d . 1 1 . .
    H H11 0.1495 -0.0443 0.2448 0.096 Uiso calc R 1 1 . .
    C C12 0.28855(17) 0.0040(3) 0.2146(3) 0.0684(6) Uani d . 1 1 . .
    H H12 0.3234 -0.0768 0.2546 0.082 Uiso calc R 1 1 . .
_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.
;
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
    Cl1 C10 . 1.733(2) ?
    N1 C1 . 1.347(2) y
    N1 C4 . 1.366(2) y
    N1 H1 . 0.864(9) ?
    N2 C5 . 1.279(2) y
    N2 C7 . 1.421(2) y
    C1 C2 . 1.358(3) y
    C1 H1A . 0.9300 ?
    C2 C3 . 1.386(3) y
    C2 H2 . 0.9300 ?
    C3 C4 . 1.376(3) y
    C3 H3 . 0.9300 ?
    C4 C5 . 1.441(3) y
    C5 C6 . 1.500(3) ?
    C6 H6A . 0.9600 ?
    C6 H6B . 0.9600 ?
    C6 H6C . 0.9600 ?
    C6 H6D . 0.9600 ?
    C6 H6E . 0.9600 ?
    C6 H6F . 0.9600 ?
    C7 C12 . 1.372(3) ?
    C7 C8 . 1.375(3) ?
    C8 C9 . 1.378(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.359(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.360(4) ?
    C11 C12 . 1.382(3) ?
    C11 H11 . 0.9300 ?
    C12 H12 . 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
    C1 N1 C4 . . 109.63(16) y
    C1 N1 H1 . . 125.1(14) ?
    C4 N1 H1 . . 125.3(14) ?
    C5 N2 C7 . . 118.67(15) ?
    N1 C1 C2 . . 108.60(19) y
    N1 C1 H1A . . 125.7 ?
    C2 C1 H1A . . 125.7 ?
    C1 C2 C3 . . 107.09(19) y
    C1 C2 H2 . . 126.5 ?
    C3 C2 H2 . . 126.5 ?
    C4 C3 C2 . . 108.32(19) y
    C4 C3 H3 . . 125.8 ?
    C2 C3 H3 . . 125.8 ?
    N1 C4 C3 . . 106.37(17) y
    N1 C4 C5 . . 123.05(16) y
    C3 C4 C5 . . 130.51(18) ?
    N2 C5 C4 . . 119.87(16) y
    N2 C5 C6 . . 123.49(18) ?
    C4 C5 C6 . . 116.64(17) ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    C5 C6 H6D . . 109.5 ?
    H6A C6 H6D . . 141.1 ?
    H6B C6 H6D . . 56.3 ?
    H6C C6 H6D . . 56.3 ?
    C5 C6 H6E . . 109.5 ?
    H6A C6 H6E . . 56.3 ?
    H6B C6 H6E . . 141.1 ?
    H6C C6 H6E . . 56.3 ?
    H6D C6 H6E . . 109.5 ?
    C5 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 . . 118.71(19) ?
    C12 C7 N2 . . 120.34(19) ?
    C8 C7 N2 . . 120.78(18) ?
    C7 C8 C9 . . 120.7(2) ?
    C7 C8 H8 . . 119.6 ?
    C9 C8 H8 . . 119.6 ?
    C10 C9 C8 . . 119.6(2) ?
    C10 C9 H9 . . 120.2 ?
    C8 C9 H9 . . 120.2 ?
    C9 C10 C11 . . 120.8(2) ?
    C9 C10 Cl1 . . 119.8(2) ?
    C11 C10 Cl1 . . 119.4(2) ?
    C10 C11 C12 . . 119.6(2) ?
    C10 C11 H11 . . 120.2 ?
    C12 C11 H11 . . 120.2 ?
    C7 C12 C11 . . 120.6(2) ?
    C7 C12 H12 . . 119.7 ?
    C11 C12 H12 . . 119.7 ?
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 . . . . 0.2(2) ?
    N1 C1 C2 C3 . . . . -0.1(3) ?
    C1 C2 C3 C4 . . . . 0.0(3) ?
    C1 N1 C4 C3 . . . . -0.2(2) ?
    C1 N1 C4 C5 . . . . 177.04(18) ?
    C2 C3 C4 N1 . . . . 0.1(2) ?
    C2 C3 C4 C5 . . . . -176.9(2) ?
    C7 N2 C5 C4 . . . . -179.02(17) ?
    C7 N2 C5 C6 . . . . 0.1(3) ?
    N1 C4 C5 N2 . . . . 0.1(3) ?
    C3 C4 C5 N2 . . . . 176.7(2) ?
    N1 C4 C5 C6 . . . . -179.0(2) ?
    C3 C4 C5 C6 . . . . -2.5(3) ?
    C5 N2 C7 C12 . . . . -95.2(2) ?
    C5 N2 C7 C8 . . . . 89.7(2) y
    C12 C7 C8 C9 . . . . 1.6(3) ?
    N2 C7 C8 C9 . . . . 176.8(2) ?
    C7 C8 C9 C10 . . . . -0.1(4) ?
    C8 C9 C10 C11 . . . . -1.2(4) ?
    C8 C9 C10 Cl1 . . . . 178.79(19) ?
    C9 C10 C11 C12 . . . . 0.9(4) ?
    Cl1 C10 C11 C12 . . . . -179.13(19) ?
    C8 C7 C12 C11 . . . . -2.0(3) ?
    N2 C7 C12 C11 . . . . -177.2(2) ?
    C10 C11 C12 C7 . . . . 0.7(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
    N1 H1 N2 3_655 0.864(9) 2.270(12) 3.080(2) 156.3(18)
    C1 H1A Cg1 3_655 0.93 2.80 3.5740(10)
                                        142.0
data_global
_journal_date_recd_electronic     2012-12-04
_journal_date_accepted     2013-03-21
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     522
_journal_page_last     525
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270113007889
_journal_coeditor_code     MX3093
_publ_contact_author_name     'Bi-Yun Su'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering
Xi'an ShiYou University
Xi'an
Shaanxi 710065
People's Republic of China
;
_publ_contact_author_email     subiyun@xsyu.edu.cn
_publ_contact_author_fax     '86 29 88383567'
_publ_contact_author_phone     '86 29 88383567'
_publ_section_title
;
Isomeric 3- and 4-chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline
;
loop_
    _publ_author_name
    _publ_author_address
    'Bi-Yun Su'
;
College of Chemistry and Chemical Engineering
Xi'an ShiYou University
Xi'an
Shaanxi 710065
People's Republic of China
;
    'Jia-Xiang Wang'
;
College of Chemistry and Chemical Engineering
Xi'an ShiYou University
Xi'an
Shaanxi 710065
People's Republic of China
;
    'Xiang Liu'
;
College of Chemistry and Chemical Engineering
Xi'an ShiYou University
Xi'an
Shaanxi 710065
People's Republic of China
;
    'Qian-Ding Li'
;
College of Chemistry and Chemical Engineering
Xi'an ShiYou University
Xi'an
Shaanxi 710065
People's Republic of China
;
