# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_audit_block_doi                 10.5517/ccdc.csd.cc1pjlsl
_database_code_depnum_ccdc_archive 'CCDC 1565090'
_audit_update_record             
;
2018-08-07 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
ethyl (2E)-2-cyano-3-[(4-fluorophenyl)amino]prop-2-enoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 F N2 O2'
_chemical_formula_sum            'C12 H11 F N2 O2'
_chemical_formula_weight         234.23

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0897(3)
_cell_length_b                   11.9762(6)
_cell_length_c                   14.5170(7)
_cell_angle_alpha                80.459(4)
_cell_angle_beta                 85.215(4)
_cell_angle_gamma                73.346(4)
_cell_volume                     1163.72(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5944
_cell_measurement_theta_min      3.8840
_cell_measurement_theta_max      28.8870

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30162
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.371
_diffrn_reflns_theta_max         29.126
_diffrn_reflns_theta_full        27.500
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5793
_reflns_number_gt                3746
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,2012)'
_computing_publication_material  'Bruker SHELXTL(Bruker, 2002)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+0.5416P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5793
_refine_ls_number_parameters     374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.2597(4) 0.59144(17) 0.58081(14) 0.0646(6) Uani 1 1 d . . . . .
N2' N 0.2848(4) 0.72712(18) 0.37606(15) 0.0672(6) Uani 1 1 d . . . . .
O2' O 0.3235(2) 0.99566(12) 0.27530(9) 0.0469(4) Uani 1 1 d . . . . .
O2 O 0.2191(2) 0.32888(12) 0.69032(10) 0.0525(4) Uani 1 1 d . . . . .
F1 F 0.2353(3) 0.48168(14) -0.00622(9) 0.0805(5) Uani 1 1 d . . . . .
O1 O 0.2221(3) 0.20445(13) 0.59008(11) 0.0594(5) Uani 1 1 d . . . . .
F1' F 0.1717(3) 0.84824(15) 0.97148(10) 0.0902(6) Uani 1 1 d . . . . .
N1 N 0.2540(3) 0.47608(16) 0.37191(12) 0.0442(4) Uani 1 1 d . . . . .
N1' N 0.2499(3) 0.84332(16) 0.59171(12) 0.0459(4) Uani 1 1 d . . . . .
O1' O 0.2771(3) 1.11963(14) 0.38009(11) 0.0707(5) Uani 1 1 d . . . . .
C2 C 0.2395(3) 0.39851(17) 0.53365(14) 0.0402(5) Uani 1 1 d . . . . .
C3 C 0.2403(3) 0.39076(18) 0.44122(14) 0.0408(5) Uani 1 1 d . . . . .
C5 C 0.2479(3) 0.47397(17) 0.27543(14) 0.0402(5) Uani 1 1 d . . . . .
C1' C 0.2924(3) 1.02259(18) 0.36210(15) 0.0444(5) Uani 1 1 d . . . . .
C4 C 0.2512(3) 0.50399(18) 0.56182(14) 0.0443(5) Uani 1 1 d . . . . .
C2' C 0.2764(3) 0.92131(18) 0.43024(14) 0.0422(5) Uani 1 1 d . . . . .
C4' C 0.2818(3) 0.81440(19) 0.39844(15) 0.0465(5) Uani 1 1 d . . . . .
C5' C 0.2303(3) 0.84960(18) 0.68849(14) 0.0418(5) Uani 1 1 d . . . . .
C3' C 0.2607(3) 0.92997(19) 0.52333(15) 0.0439(5) Uani 1 1 d . . . . .
C6 C 0.1579(4) 0.40241(19) 0.24146(16) 0.0491(6) Uani 1 1 d . . . . .
C6' C 0.1631(3) 0.9546(2) 0.72401(16) 0.0478(5) Uani 1 1 d . . . . .
C1 C 0.2261(3) 0.29971(17) 0.60483(14) 0.0421(5) Uani 1 1 d . . . . .
C8 C 0.2406(4) 0.4788(2) 0.08773(15) 0.0543(6) Uani 1 1 d . . . . .
C10 C 0.3338(4) 0.5484(2) 0.21422(17) 0.0547(6) Uani 1 1 d . . . . .
C11' C 0.3203(4) 1.0940(2) 0.20182(16) 0.0508(6) Uani 1 1 d . . . . .
C10' C 0.2769(4) 0.7439(2) 0.74934(17) 0.0503(6) Uani 1 1 d . . . . .
C7' C 0.1428(4) 0.9536(2) 0.81966(17) 0.0543(6) Uani 1 1 d . . . . .
C7 C 0.1556(4) 0.4046(2) 0.14579(16) 0.0545(6) Uani 1 1 d . . . . .
C8' C 0.1915(4) 0.8482(2) 0.87727(15) 0.0557(6) Uani 1 1 d . . . . .
C9' C 0.2583(4) 0.7434(2) 0.84395(17) 0.0569(6) Uani 1 1 d . . . . .
C9 C 0.3294(4) 0.5510(2) 0.11948(17) 0.0611(7) Uani 1 1 d . . . . .
C11 C 0.2021(5) 0.2388(2) 0.76734(17) 0.0610(7) Uani 1 1 d . . . . .
C12' C 0.3691(4) 1.0454(3) 0.11121(16) 0.0721(8) Uani 1 1 d . . . . .
H12D H 0.274723 1.005112 0.101797 0.108 Uiso 1 1 calc R U . . .
H12F H 0.498618 0.991231 0.113128 0.108 Uiso 1 1 calc R U . . .
H12E H 0.365254 1.108816 0.060718 0.108 Uiso 1 1 calc R U . . .
C12 C 0.2307(5) 0.2799(3) 0.85404(17) 0.0869(10) Uani 1 1 d . . . . .
H12B H 0.145363 0.357978 0.855754 0.130 Uiso 1 1 calc R U . . .
H12A H 0.365276 0.280936 0.855770 0.130 Uiso 1 1 calc R U . . .
H12C H 0.200155 0.227637 0.907059 0.130 Uiso 1 1 calc R U . . .
H6' H 0.125(3) 1.026(2) 0.6847(15) 0.051(6) Uiso 1 1 d . . . . .
H10' H 0.324(3) 0.675(2) 0.7218(15) 0.056(7) Uiso 1 1 d . . . . .
H1 H 0.272(3) 0.537(2) 0.3871(15) 0.052(7) Uiso 1 1 d . . . . .
H3 H 0.232(3) 0.3190(18) 0.4231(13) 0.042(6) Uiso 1 1 d . . . . .
H3' H 0.256(3) 1.0029(19) 0.5457(15) 0.051(6) Uiso 1 1 d . . . . .
H9' H 0.293(4) 0.668(2) 0.8866(18) 0.077(8) Uiso 1 1 d . . . . .
H11C H 0.421(3) 1.131(2) 0.2171(16) 0.060(7) Uiso 1 1 d . . . . .
H11D H 0.185(4) 1.150(2) 0.2030(15) 0.059(7) Uiso 1 1 d . . . . .
H6 H 0.092(3) 0.355(2) 0.2822(16) 0.060(7) Uiso 1 1 d . . . . .
H7 H 0.087(4) 0.355(2) 0.1205(16) 0.067(7) Uiso 1 1 d . . . . .
H9 H 0.388(4) 0.601(2) 0.0750(19) 0.087(9) Uiso 1 1 d . . . . .
H10 H 0.397(4) 0.594(2) 0.2417(17) 0.074(8) Uiso 1 1 d . . . . .
H1' H 0.261(3) 0.771(2) 0.5753(16) 0.062(7) Uiso 1 1 d . . . . .
H7' H 0.093(4) 1.022(2) 0.8477(17) 0.069(8) Uiso 1 1 d . . . . .
H11A H 0.301(3) 0.166(2) 0.7562(16) 0.059(7) Uiso 1 1 d . . . . .
H11B H 0.063(5) 0.228(3) 0.769(2) 0.100(11) Uiso 1 1 d . . . . .


_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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C4 1.145(3) . ?
N2' C4' 1.139(3) . ?
O2' C1' 1.337(2) . ?
O2' C11' 1.448(2) . ?
O2 C1 1.337(2) . ?
O2 C11 1.442(3) . ?
F1 C8 1.362(2) . ?
O1 C1 1.204(2) . ?
F1' C8' 1.363(3) . ?
N1 C3 1.329(2) . ?
N1 C5 1.410(3) . ?
N1 H1 0.85(2) . ?
N1' C3' 1.326(3) . ?
N1' C5' 1.413(3) . ?
N1' H1' 0.92(2) . ?
O1' C1' 1.206(2) . ?
C2 C3 1.360(3) . ?
C2 C4 1.417(3) . ?
C2 C1 1.456(3) . ?
C3 H3 0.96(2) . ?
C5 C6 1.375(3) . ?
C5 C10 1.384(3) . ?
C1' C2' 1.458(3) . ?
C2' C3' 1.365(3) . ?
C2' C4' 1.421(3) . ?
C5' C6' 1.380(3) . ?
C5' C10' 1.389(3) . ?
C3' H3' 0.97(2) . ?
C6 C7 1.386(3) . ?
C6 H6 0.94(2) . ?
C6' C7' 1.382(3) . ?
C6' H6' 0.93(2) . ?
C8 C7 1.356(3) . ?
C8 C9 1.360(3) . ?
C10 C9 1.373(3) . ?
C10 H10 0.95(3) . ?
C11' C12' 1.500(3) . ?
C11' H11C 0.99(2) . ?
C11' H11D 1.00(2) . ?
C10' C9' 1.368(3) . ?
C10' H10' 0.94(2) . ?
C7' C8' 1.364(3) . ?
C7' H7' 0.94(3) . ?
C7 H7 1.00(2) . ?
C8' C9' 1.362(3) . ?
C9' H9' 0.99(3) . ?
C9 H9 0.96(3) . ?
C11 C12 1.474(4) . ?
C11 H11A 0.97(2) . ?
C11 H11B 1.03(3) . ?
C12' H12D 0.9600 . ?
C12' H12F 0.9600 . ?
C12' H12E 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1' O2' C11' 115.38(16) . . ?
C1 O2 C11 116.01(17) . . ?
C3 N1 C5 126.92(19) . . ?
C3 N1 H1 116.6(15) . . ?
C5 N1 H1 116.4(15) . . ?
C3' N1' C5' 126.60(19) . . ?
C3' N1' H1' 117.4(15) . . ?
C5' N1' H1' 115.9(15) . . ?
C3 C2 C4 119.97(18) . . ?
C3 C2 C1 120.95(18) . . ?
C4 C2 C1 119.08(18) . . ?
N1 C3 C2 124.8(2) . . ?
N1 C3 H3 116.0(12) . . ?
C2 C3 H3 119.2(12) . . ?
C6 C5 C10 120.0(2) . . ?
C6 C5 N1 122.20(18) . . ?
C10 C5 N1 117.8(2) . . ?
O1' C1' O2' 123.28(19) . . ?
O1' C1' C2' 125.2(2) . . ?
O2' C1' C2' 111.55(17) . . ?
N2 C4 C2 177.2(2) . . ?
C3' C2' C4' 121.21(19) . . ?
C3' C2' C1' 119.57(19) . . ?
C4' C2' C1' 119.21(18) . . ?
N2' C4' C2' 177.6(2) . . ?
C6' C5' C10' 119.6(2) . . ?
C6' C5' N1' 123.03(19) . . ?
C10' C5' N1' 117.4(2) . . ?
N1' C3' C2' 125.0(2) . . ?
N1' C3' H3' 113.2(13) . . ?
C2' C3' H3' 121.8(13) . . ?
C5 C6 C7 119.6(2) . . ?
C5 C6 H6 120.9(14) . . ?
C7 C6 H6 119.4(14) . . ?
C5' C6' C7' 119.8(2) . . ?
C5' C6' H6' 120.9(14) . . ?
C7' C6' H6' 119.2(14) . . ?
O1 C1 O2 123.93(18) . . ?
O1 C1 C2 125.52(19) . . ?
O2 C1 C2 110.56(17) . . ?
C7 C8 C9 122.7(2) . . ?
C7 C8 F1 118.6(2) . . ?
C9 C8 F1 118.8(2) . . ?
C9 C10 C5 120.1(2) . . ?
C9 C10 H10 123.6(15) . . ?
C5 C10 H10 116.3(15) . . ?
O2' C11' C12' 107.4(2) . . ?
O2' C11' H11C 106.3(13) . . ?
C12' C11' H11C 112.3(13) . . ?
O2' C11' H11D 107.5(13) . . ?
C12' C11' H11D 112.0(13) . . ?
H11C C11' H11D 111.0(19) . . ?
C9' C10' C5' 120.5(2) . . ?
C9' C10' H10' 123.0(14) . . ?
C5' C10' H10' 116.5(14) . . ?
C8' C7' C6' 119.0(2) . . ?
C8' C7' H7' 117.5(15) . . ?
C6' C7' H7' 123.5(15) . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.9(14) . . ?
C6 C7 H7 120.1(14) . . ?
C9' C8' F1' 119.1(2) . . ?
C9' C8' C7' 122.3(2) . . ?
F1' C8' C7' 118.6(2) . . ?
C8' C9' C10' 118.8(2) . . ?
C8' C9' H9' 121.4(15) . . ?
C10' C9' H9' 119.8(15) . . ?
C8 C9 C10 118.7(2) . . ?
C8 C9 H9 118.8(17) . . ?
C10 C9 H9 122.5(17) . . ?
O2 C11 C12 107.6(2) . . ?
O2 C11 H11A 107.4(14) . . ?
C12 C11 H11A 113.2(14) . . ?
O2 C11 H11B 108.8(17) . . ?
C12 C11 H11B 109.7(17) . . ?
H11A C11 H11B 110(2) . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12F C12' H12E 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C3 C2 -177.4(2) . . . . ?
C4 C2 C3 N1 0.9(3) . . . . ?
C1 C2 C3 N1 -179.3(2) . . . . ?
C3 N1 C5 C6 24.1(3) . . . . ?
C3 N1 C5 C10 -156.8(2) . . . . ?
C11' O2' C1' O1' -5.4(3) . . . . ?
C11' O2' C1' C2' 173.62(19) . . . . ?
O1' C1' C2' C3' -6.4(4) . . . . ?
O2' C1' C2' C3' 174.59(19) . . . . ?
O1' C1' C2' C4' 175.0(2) . . . . ?
O2' C1' C2' C4' -4.0(3) . . . . ?
C3' N1' C5' C6' 19.5(3) . . . . ?
C3' N1' C5' C10' -162.2(2) . . . . ?
C5' N1' C3' C2' -178.9(2) . . . . ?
C4' C2' C3' N1' 0.2(4) . . . . ?
C1' C2' C3' N1' -178.4(2) . . . . ?
C10 C5 C6 C7 0.6(4) . . . . ?
N1 C5 C6 C7 179.6(2) . . . . ?
C10' C5' C6' C7' 0.0(3) . . . . ?
N1' C5' C6' C7' 178.3(2) . . . . ?
C11 O2 C1 O1 -1.2(3) . . . . ?
C11 O2 C1 C2 179.0(2) . . . . ?
C3 C2 C1 O1 2.9(4) . . . . ?
C4 C2 C1 O1 -177.3(2) . . . . ?
C3 C2 C1 O2 -177.25(19) . . . . ?
C4 C2 C1 O2 2.5(3) . . . . ?
C6 C5 C10 C9 0.0(4) . . . . ?
N1 C5 C10 C9 -179.1(2) . . . . ?
C1' O2' C11' C12' 176.8(2) . . . . ?
C6' C5' C10' C9' -0.6(3) . . . . ?
N1' C5' C10' C9' -179.0(2) . . . . ?
C5' C6' C7' C8' 0.5(4) . . . . ?
C9 C8 C7 C6 0.4(4) . . . . ?
F1 C8 C7 C6 -179.1(2) . . . . ?
C5 C6 C7 C8 -0.8(4) . . . . ?
C6' C7' C8' C9' -0.5(4) . . . . ?
C6' C7' C8' F1' 179.8(2) . . . . ?
F1' C8' C9' C10' 179.7(2) . . . . ?
C7' C8' C9' C10' -0.1(4) . . . . ?
C5' C10' C9' C8' 0.7(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
F1 C8 C9 C10 179.7(2) . . . . ?
C5 C10 C9 C8 -0.4(4) . . . . ?
C1 O2 C11 C12 170.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 N2' 0.85(2) 2.28(2) 3.087(3) 160(2) . yes
N1' H1' N2 0.92(2) 2.14(3) 3.027(3) 163(2) . yes
C3 H3 O1' 0.96(2) 2.49(2) 3.439(3) 169.6(16) 1_545 yes
C3' H3' O1 0.97(2) 2.54(2) 3.509(3) 174.3(17) 1_565 yes

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 952089'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2018-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
ethyl (E)-3-[(4-cholorophenyl)amino]-2-cyanoprop-2-enoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Cl N2 O2'
_chemical_formula_sum            'C12 H11 Cl N2 O2'
_chemical_formula_weight         250.68

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0911(3)
_cell_length_b                   12.042(3)
_cell_length_c                   15.295(3)
_cell_angle_alpha                80.159(3)
_cell_angle_beta                 89.087(3)
_cell_angle_gamma                74.739(3)
_cell_volume                     1240.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4400
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      25.0

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.299
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_correction_T_max  0.9427
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_special_details   
;
?
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13352
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.780
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4400
_reflns_number_gt                3071
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2(Bruker, 2002)'
_computing_cell_refinement       'Bruker SAINT(Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT(Bruker, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia,2012)'
_computing_publication_material  'Bruker SHELXTL(Bruker, 2002)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²+0.3492P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4400
_refine_ls_number_parameters     367
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2296(4) -0.2013(2) 0.60144(15) 0.0546(4) Uani 1 1 d . . . . .
C2 C 0.2382(3) -0.10154(18) 0.53402(14) 0.0409(5) Uani 1 1 d . . . . .
C3 C 0.2337(3) -0.1080(2) 0.44625(14) 0.0412(5) Uani 1 1 d . . . . .
H3 H 0.227(3) -0.1777(19) 0.4286(13) 0.041(6) Uiso 1 1 d . . . . .
C4 C 0.2523(3) 0.0034(2) 0.56123(14) 0.0448(5) Uani 1 1 d . . . . .
C5 C 0.2368(3) -0.02611(18) 0.28870(13) 0.0407(5) Uani 1 1 d . . . . .
C6 C 0.1490(4) -0.1002(2) 0.25523(15) 0.0490(6) Uani 1 1 d . . . . .
H6 H 0.086(4) -0.148(2) 0.2941(16) 0.066(8) Uiso 1 1 d . . . . .
C7 C 0.1525(4) -0.1031(2) 0.16540(15) 0.0509(6) Uani 1 1 d . . . . .
H7 H 0.086(3) -0.154(2) 0.1429(15) 0.060(7) Uiso 1 1 d . . . . .
C8 C 0.2424(3) -0.0325(2) 0.10986(14) 0.0473(6) Uani 1 1 d . . . . .
C9 C 0.3253(4) 0.0446(2) 0.14196(16) 0.0549(6) Uani 1 1 d . . . . .
H9 H 0.386(4) 0.091(2) 0.1009(17) 0.070(8) Uiso 1 1 d . . . . .
C10 C 0.3223(4) 0.0474(2) 0.23148(15) 0.0504(6) Uani 1 1 d . . . . .
H10 H 0.385(4) 0.096(2) 0.2557(16) 0.062(7) Uiso 1 1 d . . . . .
C11 C 0.2131(6) -0.2654(2) 0.75515(16) 0.0668(8) Uani 1 1 d . . . . .
H11A H 0.316(4) -0.336(2) 0.7488(15) 0.058(7) Uiso 1 1 d . . . . .
H11B H 0.076(5) -0.277(3) 0.757(2) 0.116(13) Uiso 1 1 d . . . . .
C12 C 0.2343(6) -0.2236(3) 0.83902(17) 0.0879(10) Uani 1 1 d . . . . .
H12A H 0.2152 -0.2802 0.8883 0.132 Uiso 1 1 calc R U . . .
H12B H 0.3630 -0.2129 0.8437 0.132 Uiso 1 1 calc R U . . .
H12C H 0.1385 -0.1506 0.8395 0.132 Uiso 1 1 calc R U . . .
N1 N 0.2419(3) -0.02198(17) 0.38021(11) 0.0437(5) Uani 1 1 d . . . . .
H1 H 0.259(4) 0.042(2) 0.3931(16) 0.058(8) Uiso 1 1 d . . . . .
N2 N 0.2633(4) 0.08970(19) 0.57896(14) 0.0666(6) Uani 1 1 d . . . . .
O1 O 0.2251(3) -0.29618(13) 0.58702(10) 0.0546(4) Uani 1 1 d . . . . .
O2 O 0.2269(3) -0.17388(13) 0.68264(9) 0.0556(5) Uani 1 1 d . . . . .
Cl1 Cl 0.25498(11) -0.04196(7) -0.00245(4) 0.0728(2) Uani 1 1 d . . . . .
C1' C 0.2857(3) 0.5212(2) 0.36805(14) 0.0461(5) Uani 1 1 d . . . . .
C2' C 0.2750(3) 0.41951(18) 0.43378(14) 0.0431(5) Uani 1 1 d . . . . .
C3' C 0.2645(3) 0.4272(2) 0.52143(15) 0.0443(5) Uani 1 1 d . . . . .
H3' H 0.264(3) 0.499(2) 0.5369(14) 0.049(6) Uiso 1 1 d . . . . .
C4' C 0.2776(4) 0.3130(2) 0.40449(14) 0.0464(6) Uani 1 1 d . . . . .
C5' C 0.2444(3) 0.34534(18) 0.67867(14) 0.0411(5) Uani 1 1 d . . . . .
C6' C 0.1825(4) 0.4493(2) 0.71079(15) 0.0473(6) Uani 1 1 d . . . . .
H6' H 0.144(4) 0.522(2) 0.6730(16) 0.061(7) Uiso 1 1 d . . . . .
C7' C 0.1714(4) 0.4475(2) 0.80129(16) 0.0531(6) Uani 1 1 d . . . . .
H7' H 0.122(4) 0.516(2) 0.8233(16) 0.061(7) Uiso 1 1 d . . . . .
C8' C 0.2204(4) 0.3434(2) 0.85931(15) 0.0511(6) Uani 1 1 d . . . . .
C9' C 0.2824(4) 0.2391(2) 0.82836(16) 0.0521(6) Uani 1 1 d . . . . .
H9' H 0.317(3) 0.163(2) 0.8700(16) 0.061(7) Uiso 1 1 d . . . . .
C10' C 0.2928(4) 0.2407(2) 0.73869(16) 0.0498(6) Uani 1 1 d . . . . .
H10' H 0.336(4) 0.173(2) 0.7176(16) 0.060(7) Uiso 1 1 d . . . . .
C11' C 0.3009(5) 0.5922(2) 0.21474(16) 0.0546(6) Uani 1 1 d . . . . .
H11C H 0.401(4) 0.627(2) 0.2272(16) 0.068(8) Uiso 1 1 d . . . . .
H11D H 0.168(4) 0.647(2) 0.2153(14) 0.052(7) Uiso 1 1 d . . . . .
C12' C 0.3349(5) 0.5447(3) 0.12987(16) 0.0760(8) Uani 1 1 d . . . . .
H12D H 0.4635 0.4923 0.1320 0.114 Uiso 1 1 calc R U . . .
H12F H 0.3237 0.6079 0.0810 0.114 Uiso 1 1 calc R U . . .
H12E H 0.2392 0.5033 0.1222 0.114 Uiso 1 1 calc R U . . .
N1' N 0.2572(3) 0.34034(17) 0.58732(12) 0.0455(5) Uani 1 1 d . . . . .
H1' H 0.268(3) 0.273(2) 0.5736(15) 0.053(7) Uiso 1 1 d . . . . .
N2' N 0.2787(4) 0.22625(19) 0.38384(14) 0.0667(6) Uani 1 1 d . . . . .
O1' O 0.2741(3) 0.61745(15) 0.38405(11) 0.0700(6) Uani 1 1 d . . . . .
O2' O 0.3103(2) 0.49437(13) 0.28618(9) 0.0501(4) Uani 1 1 d . . . . .
Cl1' Cl 0.20570(14) 0.34291(7) 0.97328(4) 0.0870(3) Uani 1 1 d . . . . .


_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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C4 1.140(3) . ?
N2' C4' 1.140(3) . ?
Cl1' C8' 1.744(2) . ?
Cl1 C8 1.740(2) . ?
O2' C1' 1.343(3) . ?
O2' C11' 1.452(3) . ?
O1 C1 1.208(2) . ?
O1' C1' 1.207(3) . ?
O2 C1 1.337(3) . ?
O2 C11 1.445(3) . ?
N1 C3 1.330(3) . ?
N1 C5 1.410(3) . ?
N1 H1 0.86(3) . ?
N1' C3' 1.334(3) . ?
N1' C5' 1.409(3) . ?
N1' H1' 0.86(2) . ?
C2' C3' 1.359(3) . ?
C2' C4' 1.425(3) . ?
C2' C1' 1.464(3) . ?
C3 C2 1.359(3) . ?
C3 H3 0.94(2) . ?
C3' H3' 0.94(2) . ?
C5 C6 1.380(3) . ?
C5 C10 1.385(3) . ?
C1 C2 1.457(3) . ?
C8 C7 1.369(3) . ?
C8 C9 1.378(3) . ?
C5' C6' 1.384(3) . ?
C5' C10' 1.391(3) . ?
C4 C2 1.424(3) . ?
C7' C8' 1.371(3) . ?
C7' C6' 1.382(3) . ?
C7' H7' 0.92(3) . ?
C8' C9' 1.378(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.95(3) . ?
C10 C9 1.375(3) . ?
C10 H10 0.95(2) . ?
C7 H7 0.97(2) . ?
C10' C9' 1.369(3) . ?
C10' H10' 0.91(2) . ?
C11' C12' 1.497(4) . ?
C11' H11C 0.95(3) . ?
C11' H11D 1.00(2) . ?
C6' H6' 0.93(2) . ?
C12' H12D 0.9600 . ?
C12' H12F 0.9600 . ?
C12' H12E 0.9600 . ?
C9' H9' 1.00(2) . ?
C9 H9 0.95(3) . ?
C11 C12 1.479(4) . ?
C11 H11A 0.98(2) . ?
C11 H11B 1.01(3) . ?
C12 H12B 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N2 H1' 164.1(6) . . ?
C1' O2' C11' 115.57(18) . . ?
C1 O2 C11 115.72(18) . . ?
C3 N1 C5 126.3(2) . . ?
C3 N1 H1 118.5(16) . . ?
C5 N1 H1 115.1(16) . . ?
C3' N1' C5' 127.0(2) . . ?
C3' N1' H1' 117.3(16) . . ?
C5' N1' H1' 115.6(16) . . ?
C3' C2' C4' 121.0(2) . . ?
C3' C2' C1' 120.0(2) . . ?
C4' C2' C1' 119.05(19) . . ?
N1 C3 C2 125.0(2) . . ?
N1 C3 H3 115.1(13) . . ?
C2 C3 H3 119.9(13) . . ?
N1' C3' C2' 125.4(2) . . ?
N1' C3' H3' 117.3(14) . . ?
C2' C3' H3' 117.3(14) . . ?
C6 C5 C10 119.7(2) . . ?
C6 C5 N1 122.0(2) . . ?
C10 C5 N1 118.3(2) . . ?
O1 C1 O2 124.0(2) . . ?
O1 C1 C2 125.4(2) . . ?
O2 C1 C2 110.65(18) . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 Cl1 119.35(18) . . ?
C9 C8 Cl1 119.77(18) . . ?
O1' C1' O2' 123.5(2) . . ?
O1' C1' C2' 125.2(2) . . ?
O2' C1' C2' 111.33(19) . . ?
C6' C5' C10' 118.9(2) . . ?
C6' C5' N1' 122.9(2) . . ?
C10' C5' N1' 118.2(2) . . ?
N2 C4 C2 176.8(2) . . ?
C3 C2 C4 120.12(19) . . ?
C3 C2 C1 120.79(19) . . ?
C4 C2 C1 119.08(19) . . ?
C8' C7' C6' 120.4(2) . . ?
C8' C7' H7' 119.0(15) . . ?
C6' C7' H7' 120.4(15) . . ?
C7' C8' C9' 120.6(2) . . ?
C7' C8' Cl1' 119.73(19) . . ?
C9' C8' Cl1' 119.69(19) . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.6(15) . . ?
C5 C6 H6 119.6(15) . . ?
C9 C10 C5 120.4(2) . . ?
C9 C10 H10 120.8(15) . . ?
C5 C10 H10 118.7(15) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 121.5(14) . . ?
C6 C7 H7 118.5(14) . . ?
C9' C10' C5' 121.3(2) . . ?
C9' C10' H10' 119.9(15) . . ?
C5' C10' H10' 118.8(15) . . ?
O2' C11' C12' 107.5(2) . . ?
O2' C11' H11C 106.9(15) . . ?
C12' C11' H11C 111.5(15) . . ?
O2' C11' H11D 106.8(13) . . ?
C12' C11' H11D 111.9(13) . . ?
H11C C11' H11D 112(2) . . ?
C7' C6' C5' 119.7(2) . . ?
C7' C6' H6' 118.2(15) . . ?
C5' C6' H6' 122.1(15) . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
H12F C12' H12E 109.5 . . ?
C10' C9' C8' 119.1(2) . . ?
C10' C9' H9' 119.6(14) . . ?
C8' C9' H9' 121.2(14) . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 123.1(15) . . ?
C8 C9 H9 117.6(15) . . ?
O2 C11 C12 107.7(2) . . ?
O2 C11 H11A 107.8(14) . . ?
C12 C11 H11A 112.6(14) . . ?
O2 C11 H11B 110(2) . . ?
C12 C11 H11B 103.9(19) . . ?
H11A C11 H11B 114(3) . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
N2' C4' C2' 177.7(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C3 C2 -179.8(2) . . . . ?
C5' N1' C3' C2' -179.3(2) . . . . ?
C4' C2' C3' N1' 0.5(4) . . . . ?
C1' C2' C3' N1' -178.9(2) . . . . ?
C3 N1 C5 C6 25.8(3) . . . . ?
C3 N1 C5 C10 -154.5(2) . . . . ?
C11 O2 C1 O1 -1.5(4) . . . . ?
C11 O2 C1 C2 178.4(2) . . . . ?
C11' O2' C1' O1' -6.6(3) . . . . ?
C11' O2' C1' C2' 173.4(2) . . . . ?
C3' C2' C1' O1' -4.8(4) . . . . ?
C4' C2' C1' O1' 175.8(2) . . . . ?
C3' C2' C1' O2' 175.2(2) . . . . ?
C4' C2' C1' O2' -4.2(3) . . . . ?
C3' N1' C5' C6' 18.9(4) . . . . ?
C3' N1' C5' C10' -162.4(2) . . . . ?
N1 C3 C2 C4 0.1(4) . . . . ?
N1 C3 C2 C1 -179.6(2) . . . . ?
O1 C1 C2 C3 2.7(4) . . . . ?
O2 C1 C2 C3 -177.1(2) . . . . ?
O1 C1 C2 C4 -177.0(3) . . . . ?
O2 C1 C2 C4 3.2(3) . . . . ?
C6' C7' C8' C9' 0.3(4) . . . . ?
C6' C7' C8' Cl1' 179.92(19) . . . . ?
C10 C5 C6 C7 2.1(4) . . . . ?
N1 C5 C6 C7 -178.3(2) . . . . ?
C6 C5 C10 C9 -1.9(4) . . . . ?
N1 C5 C10 C9 178.4(2) . . . . ?
C9 C8 C7 C6 -1.9(4) . . . . ?
Cl1 C8 C7 C6 177.15(19) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6' C5' C10' C9' -0.8(4) . . . . ?
N1' C5' C10' C9' -179.6(2) . . . . ?
C1' O2' C11' C12' 179.0(2) . . . . ?
C8' C7' C6' C5' -0.3(4) . . . . ?
C10' C5' C6' C7' 0.5(3) . . . . ?
N1' C5' C6' C7' 179.2(2) . . . . ?
C5' C10' C9' C8' 0.8(4) . . . . ?
C7' C8' C9' C10' -0.6(4) . . . . ?
Cl1' C8' C9' C10' 179.8(2) . . . . ?
C5 C10 C9 C8 -0.1(4) . . . . ?
C7 C8 C9 C10 2.0(4) . . . . ?
Cl1 C8 C9 C10 -177.0(2) . . . . ?
C1 O2 C11 C12 173.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1' H1' N2 0.86(2) 2.20(3) 3.032(3) 163(2) .
N1 H1 N2' 0.86(3) 2.25(3) 3.078(3) 163(2) .
C6' H6' O1 0.93(2) 2.56(3) 3.399(3) 150(2) 1_565

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.050



