# 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 2015

####################################################################### 
# 
# 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_zzf-1
_database_code_depnum_ccdc_archive 'CCDC 952088'
_audit_update_record             
;
2013-07-24 deposited with the CCDC.
2015-08-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
ethyl (2Z)-3-[(4-bromophenyl)amino]-2-cyanoprop-2-enoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Br N2 O2'
_chemical_formula_weight         295.13

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4955(11)
_cell_length_b                   7.5254(11)
_cell_length_c                   12.0645(17)
_cell_angle_alpha                80.285(2)
_cell_angle_beta                 86.767(2)
_cell_angle_gamma                67.729(2)
_cell_volume                     620.70(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             294
_exptl_absorpt_coefficient_mu    3.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4374
_exptl_absorpt_correction_T_max  0.5580
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6597
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2189
_reflns_number_gt                1855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2008)'
_computing_cell_refinement       'SMART (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.2007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2189
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.28275(4) 0.94521(5) 0.33976(2) 0.05596(14) Uani 1 1 d . . .
N1 N 0.4610(3) 0.4644(3) 0.80486(19) 0.0462(6) Uani 1 1 d . . .
H1A H 0.5817 0.3969 0.8172 0.055 Uiso 1 1 calc R . .
N2 N 0.1416(4) 0.3400(5) 1.1386(2) 0.0741(9) Uani 1 1 d . . .
O1 O 0.7296(3) 0.1941(3) 0.94511(18) 0.0617(6) Uani 1 1 d . . .
O2 O 0.6297(3) 0.0925(3) 1.11408(16) 0.0476(5) Uani 1 1 d . . .
C8 C 0.3327(4) 0.7971(4) 0.4859(2) 0.0425(6) Uani 1 1 d . . .
C9 C 0.5159(4) 0.7329(4) 0.5315(2) 0.0511(7) Uani 1 1 d . . .
H9 H 0.6126 0.7629 0.4907 0.061 Uiso 1 1 calc R . .
C10 C 0.5542(4) 0.6248(4) 0.6369(2) 0.0501(7) Uani 1 1 d . . .
H10 H 0.6776 0.5806 0.6674 0.060 Uiso 1 1 calc R . .
C5 C 0.4111(4) 0.5813(4) 0.6980(2) 0.0417(6) Uani 1 1 d . . .
C6 C 0.2270(4) 0.6472(4) 0.6529(2) 0.0465(7) Uani 1 1 d . . .
H6 H 0.1297 0.6190 0.6941 0.056 Uiso 1 1 calc R . .
C7 C 0.1888(4) 0.7554(4) 0.5460(2) 0.0472(7) Uani 1 1 d . . .
H7 H 0.0658 0.7996 0.5150 0.057 Uiso 1 1 calc R . .
C1 C 0.3436(4) 0.4470(4) 0.8877(2) 0.0422(6) Uani 1 1 d . . .
H1 H 0.2131 0.5228 0.8774 0.051 Uiso 1 1 calc R . .
C2 C 0.4005(4) 0.3247(4) 0.9880(2) 0.0402(6) Uani 1 1 d . . .
C4 C 0.2581(4) 0.3301(4) 1.0724(2) 0.0484(7) Uani 1 1 d . . .
C3 C 0.6011(4) 0.1986(4) 1.0119(2) 0.0431(6) Uani 1 1 d . . .
C11 C 0.8283(4) -0.0327(5) 1.1434(3) 0.0555(8) Uani 1 1 d . . .
H11A H 0.9067 0.0447 1.1425 0.067 Uiso 1 1 calc R . .
H11B H 0.8809 -0.1220 1.0899 0.067 Uiso 1 1 calc R . .
C12 C 0.8271(5) -0.1419(5) 1.2579(3) 0.0590(8) Uani 1 1 d . . .
H12A H 0.7829 -0.0525 1.3108 0.089 Uiso 1 1 calc R . .
H12B H 0.9553 -0.2326 1.2782 0.089 Uiso 1 1 calc R . .
H12C H 0.7425 -0.2111 1.2588 0.089 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0555(2) 0.0636(2) 0.03836(18) 0.00654(13) 0.00142(13) -0.01701(15)
N1 0.0350(12) 0.0522(14) 0.0412(13) -0.0010(11) 0.0033(10) -0.0079(11)
N2 0.0381(15) 0.106(2) 0.0538(17) 0.0179(16) 0.0050(13) -0.0136(15)
O1 0.0384(11) 0.0756(15) 0.0507(12) 0.0031(11) 0.0115(10) -0.0055(10)
O2 0.0321(10) 0.0549(12) 0.0426(11) 0.0062(9) -0.0008(8) -0.0072(9)
C8 0.0469(16) 0.0395(15) 0.0341(14) -0.0037(11) 0.0027(12) -0.0097(12)
C9 0.0493(18) 0.0588(19) 0.0440(16) -0.0012(14) 0.0038(13) -0.0223(15)
C10 0.0386(16) 0.0605(19) 0.0459(17) -0.0024(14) 0.0000(13) -0.0152(14)
C5 0.0419(16) 0.0405(15) 0.0360(14) -0.0061(12) 0.0007(12) -0.0082(12)
C6 0.0425(16) 0.0473(16) 0.0458(16) -0.0039(13) 0.0108(13) -0.0156(13)
C7 0.0442(16) 0.0488(17) 0.0426(16) -0.0007(13) -0.0013(13) -0.0132(13)
C1 0.0382(15) 0.0474(16) 0.0408(15) -0.0096(12) 0.0032(12) -0.0151(12)
C2 0.0334(14) 0.0499(16) 0.0342(14) -0.0022(12) 0.0000(11) -0.0140(12)
C4 0.0329(15) 0.0586(18) 0.0430(16) 0.0067(14) -0.0082(13) -0.0102(13)
C3 0.0393(15) 0.0460(16) 0.0411(16) -0.0067(12) 0.0044(12) -0.0133(13)
C11 0.0314(15) 0.0601(19) 0.061(2) 0.0019(15) -0.0047(14) -0.0058(14)
C12 0.0475(18) 0.0561(19) 0.064(2) 0.0064(16) -0.0146(15) -0.0134(15)

_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
Br1 C8 1.894(3) . ?
N1 C1 1.316(3) . ?
N1 C5 1.413(4) . ?
N1 H1A 0.8600 . ?
N2 C4 1.140(4) . ?
O1 C3 1.215(3) . ?
O2 C3 1.330(3) . ?
O2 C11 1.453(3) . ?
C8 C7 1.370(4) . ?
C8 C9 1.383(4) . ?
C9 C10 1.370(4) . ?
C9 H9 0.9300 . ?
C10 C5 1.377(4) . ?
C10 H10 0.9300 . ?
C5 C6 1.387(4) . ?
C6 C7 1.385(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C1 C2 1.370(4) . ?
C1 H1 0.9300 . ?
C2 C4 1.427(4) . ?
C2 C3 1.456(4) . ?
C11 C12 1.486(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 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 N1 C5 127.4(2) . . ?
C1 N1 H1A 116.3 . . ?
C5 N1 H1A 116.3 . . ?
C3 O2 C11 115.9(2) . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 Br1 120.4(2) . . ?
C9 C8 Br1 119.1(2) . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C10 C5 C6 120.0(3) . . ?
C10 C5 N1 117.7(3) . . ?
C6 C5 N1 122.3(3) . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
N1 C1 C2 124.5(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C4 118.1(2) . . ?
C1 C2 C3 122.0(2) . . ?
C4 C2 C3 119.8(2) . . ?
N2 C4 C2 178.0(3) . . ?
O1 C3 O2 123.7(3) . . ?
O1 C3 C2 122.7(3) . . ?
O2 C3 C2 113.6(2) . . ?
O2 C11 C12 107.1(2) . . ?
O2 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O2 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B 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
C7 C8 C9 C10 0.8(5) . . . . ?
Br1 C8 C9 C10 -179.7(2) . . . . ?
C8 C9 C10 C5 -0.6(5) . . . . ?
C9 C10 C5 C6 -0.1(5) . . . . ?
C9 C10 C5 N1 178.1(3) . . . . ?
C1 N1 C5 C10 160.9(3) . . . . ?
C1 N1 C5 C6 -21.0(4) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?
N1 C5 C6 C7 -177.6(3) . . . . ?
C9 C8 C7 C6 -0.3(4) . . . . ?
Br1 C8 C7 C6 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 N1 C1 C2 177.3(3) . . . . ?
N1 C1 C2 C4 176.4(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C4 N2 -32(10) . . . . ?
C3 C2 C4 N2 145(10) . . . . ?
C11 O2 C3 O1 0.2(4) . . . . ?
C11 O2 C3 C2 -178.6(2) . . . . ?
C1 C2 C3 O1 0.1(5) . . . . ?
C4 C2 C3 O1 -176.8(3) . . . . ?
C1 C2 C3 O2 179.0(3) . . . . ?
C4 C2 C3 O2 2.0(4) . . . . ?
C3 O2 C11 C12 -178.1(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 H1A O1 0.86 2.01 2.678(3) 133.3 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058
