# 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 2016

####################################################################### 
# 
# 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_modelo_final_res_01
_audit_block_doi                 10.5517/ccdc.csd.cc1k2rq3
_database_code_depnum_ccdc_archive 'CCDC 1432625'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.cplett.2016.04.070 2016
_audit_update_record             
;
2015-10-21 deposited with the CCDC.
2016-12-16 downloaded from the CCDC.
;

_audit_creation_date             2015-10-19T12:37:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H12 Br N O2'
_chemical_formula_sum            'C15 H12 Br N O2'
_chemical_formula_weight         318.17
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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                   29.476
_cell_length_b                   6.975
_cell_length_c                   13.591
_cell_angle_alpha                90
_cell_angle_beta                 112.53
_cell_angle_gamma                90
_cell_volume                     2581.2
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.181
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'Bruker TRIUMPH curved-graphite'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_measurement_method       'combination of ω and φ-scans'
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_number            33959
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.496
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.97
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 0.97
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             2275
_reflns_number_gt                2153
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0212P)²+3.7040P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2275
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0194
_refine_ls_R_factor_gt           0.0178
_refine_ls_wR_factor_ref         0.047
_refine_ls_wR_factor_gt          0.046
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Br1 Br 0.23041(2) 0.82604(3) 0.33805(2) 0.02760(7) Uani 1 1 d . . . . .
C11 C 0.06449(6) 0.6774(2) 0.17444(12) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.11623(6) -0.0787(2) -0.00150(12) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.01626(4) 0.62772(18) 0.12860(10) 0.0234(3) Uani 1 1 d . . . . .
O1 O 0.04105(4) 0.07847(17) -0.03990(10) 0.0268(3) Uani 1 1 d . . . . .
C7 C 0.17499(6) -0.3757(3) -0.02543(13) 0.0219(4) Uani 1 1 d . . . . .
H7 H 0.1945 -0.4739 -0.034 0.026 Uiso 1 1 calc R U . . .
C5 C 0.09418(6) -0.2444(2) -0.06232(12) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.08635(6) 0.0791(2) 0.01006(13) 0.0178(3) Uani 1 1 d . . . . .
C9 C 0.16804(6) -0.0717(2) 0.04618(12) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.183 0.0349 0.0868 0.021 Uiso 1 1 calc R U . . .
C3 C 0.08212(6) 0.3750(2) 0.10214(13) 0.0183(3) Uani 1 1 d . . . . .
H3 H 0.0483 0.3558 0.0731 0.022 Uiso 1 1 calc R U . . .
C10 C 0.09924(6) 0.5479(2) 0.16597(12) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.04499(6) -0.2657(2) -0.11185(13) 0.0266(3) Uani 1 1 d . . . . .
C14 C 0.16275(6) 0.7638(2) 0.27060(12) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.12855(6) 0.8936(3) 0.27699(13) 0.0199(3) Uani 1 1 d . . . . .
C12 C 0.07920(6) 0.8486(2) 0.22913(13) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.0558 0.9337 0.2337 0.024 Uiso 1 1 calc R U . . .
C6 C 0.12499(6) -0.3907(2) -0.07233(13) 0.0206(3) Uani 1 1 d . . . . .
C2 C 0.10909(6) 0.2423(2) 0.08069(13) 0.0198(3) Uani 1 1 d . . . . .
H2' H 0.1431 0.2521 0.1108 0.024 Uiso 1 1 calc R U . . .
C15 C 0.14900(6) 0.5937(2) 0.21642(12) 0.0175(3) Uani 1 1 d . . . . .
H15 H 0.1728 0.509 0.2133 0.021 Uiso 1 1 calc R U . . .
C8 C 0.19698(6) -0.2159(3) 0.03475(13) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.231 -0.2071 0.0669 0.026 Uiso 1 1 calc R U . . .
H2 H 0.0001(8) 0.721(3) 0.1064(17) 0.033 Uiso 1 1 d . U . . .
H1A H 0.0341(7) -0.373(3) -0.1322(16) 0.026 Uiso 1 1 d . U . . .
H1B H 0.0278(8) -0.184(3) -0.0990(16) 0.026 Uiso 1 1 d . U . . .
H13 H 0.1374(7) 1.009(3) 0.3123(15) 0.026 Uiso 1 1 d . U . . .
H6 H 0.1110(7) -0.497(3) -0.1112(15) 0.026 Uiso 1 1 d . U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C14 1.8989(16) . ?
C11 O2 1.360(2) . ?
C11 C12 1.386(2) . ?
C11 C10 1.403(2) . ?
C4 C9 1.413(2) . ?
C4 C5 1.425(2) . ?
C4 C1 1.456(2) . ?
O2 H2 0.79(2) . ?
O1 C1 1.245(2) . ?
C7 C6 1.367(2) . ?
C7 C8 1.388(3) . ?
C7 H7 0.93 . ?
C5 N1 1.352(2) . ?
C5 C6 1.407(2) . ?
C1 C2 1.474(2) . ?
C9 C8 1.366(2) . ?
C9 H9 0.93 . ?
C3 C2 1.324(2) . ?
C3 C10 1.458(2) . ?
C3 H3 0.93 . ?
C10 C15 1.398(2) . ?
N1 H1A 0.82(2) . ?
N1 H1B 0.83(2) . ?
C14 C15 1.373(2) . ?
C14 C13 1.382(2) . ?
C13 C12 1.383(2) . ?
C13 H13 0.92(2) . ?
C12 H12 0.93 . ?
C6 H6 0.91(2) . ?
C2 H2' 0.93 . ?
C15 H15 0.93 . ?
C8 H8 0.93 . ?

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
O2 C11 C12 121.50(15) . . ?
O2 C11 C10 117.79(14) . . ?
C12 C11 C10 120.70(15) . . ?
C9 C4 C5 117.84(14) . . ?
C9 C4 C1 121.11(14) . . ?
C5 C4 C1 121.05(14) . . ?
C11 O2 H2 109.6(16) . . ?
C6 C7 C8 120.86(16) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C5 C6 118.78(16) . . ?
N1 C5 C4 122.77(16) . . ?
C6 C5 C4 118.45(15) . . ?
O1 C1 C4 120.37(15) . . ?
O1 C1 C2 118.89(14) . . ?
C4 C1 C2 120.74(14) . . ?
C8 C9 C4 122.33(15) . . ?
C8 C9 H9 118.8 . . ?
C4 C9 H9 118.8 . . ?
C2 C3 C10 127.55(15) . . ?
C2 C3 H3 116.2 . . ?
C10 C3 H3 116.2 . . ?
C15 C10 C11 118.32(15) . . ?
C15 C10 C3 122.69(15) . . ?
C11 C10 C3 118.96(14) . . ?
C5 N1 H1A 118.3(14) . . ?
C5 N1 H1B 116.4(14) . . ?
H1A N1 H1B 121(2) . . ?
C15 C14 C13 121.80(15) . . ?
C15 C14 Br1 119.74(12) . . ?
C13 C14 Br1 118.46(13) . . ?
C14 C13 C12 118.89(16) . . ?
C14 C13 H13 122.5(12) . . ?
C12 C13 H13 118.6(12) . . ?
C13 C12 C11 120.29(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C7 C6 C5 121.35(16) . . ?
C7 C6 H6 120.1(12) . . ?
C5 C6 H6 118.6(12) . . ?
C3 C2 C1 121.46(15) . . ?
C3 C2 H2' 119.3 . . ?
C1 C2 H2' 119.3 . . ?
C14 C15 C10 119.97(15) . . ?
C14 C15 H15 120 . . ?
C10 C15 H15 120 . . ?
C9 C8 C7 119.18(16) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?

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
C9 C4 C5 N1 -179.60(15) . . . . ?
C1 C4 C5 N1 -0.3(2) . . . . ?
C9 C4 C5 C6 -0.5(2) . . . . ?
C1 C4 C5 C6 178.77(14) . . . . ?
C9 C4 C1 O1 173.68(15) . . . . ?
C5 C4 C1 O1 -5.6(2) . . . . ?
C9 C4 C1 C2 -6.2(2) . . . . ?
C5 C4 C1 C2 174.57(14) . . . . ?
C5 C4 C9 C8 0.7(2) . . . . ?
C1 C4 C9 C8 -178.58(15) . . . . ?
O2 C11 C10 C15 -177.44(14) . . . . ?
C12 C11 C10 C15 1.7(2) . . . . ?
O2 C11 C10 C3 4.7(2) . . . . ?
C12 C11 C10 C3 -176.19(14) . . . . ?
C2 C3 C10 C15 -1.4(3) . . . . ?
C2 C3 C10 C11 176.37(16) . . . . ?
C15 C14 C13 C12 1.3(2) . . . . ?
Br1 C14 C13 C12 -179.29(12) . . . . ?
C14 C13 C12 C11 -1.0(2) . . . . ?
O2 C11 C12 C13 178.56(15) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
N1 C5 C6 C7 178.96(16) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C10 C3 C2 C1 -176.87(15) . . . . ?
O1 C1 C2 C3 8.4(2) . . . . ?
C4 C1 C2 C3 -171.71(15) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
Br1 C14 C15 C10 -179.52(12) . . . . ?
C11 C10 C15 C14 -1.4(2) . . . . ?
C3 C10 C15 C14 176.41(15) . . . . ?
C4 C9 C8 C7 -0.2(2) . . . . ?
C6 C7 C8 C9 -0.5(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
O2 H2 O1 0.79(2) 1.85(2) 2.6357(18) 173(2) 5_565
N1 H1A O2 0.82(2) 2.33(2) 3.062(2) 149.4(19) 5
N1 H1B O1 0.83(2) 1.97(2) 2.611(2) 133.4(19) .

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
'(E)-1-(2-aminophenyl)-3-(3-bromo-5-hydroyphenyl)-prop-2-en-1-one '
_chemical_name_common            2-amino-chalcone
