# 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 2017

####################################################################### 
# 
# 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_4ec
_database_code_depnum_ccdc_archive 'CCDC 1426150'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(4-(bis(2-chloroethyl)amino)phenyl)-1-(4-ethylphenyl)prop-2-en-1-one
_chemical_name_common            'Ethyl chalcone'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 Cl2 N O'
_chemical_formula_weight         376.30

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                   8.4268(3)
_cell_length_b                   9.2446(3)
_cell_length_c                   12.4656(4)
_cell_angle_alpha                81.2037(13)
_cell_angle_beta                 85.3644(16)
_cell_angle_gamma                84.7588(16)
_cell_volume                     953.46(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7578
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.08

_exptl_crystal_description       BLock
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.349
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15022
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.657
_diffrn_reflns_theta_max         27.135
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4195
_reflns_number_gt                3344
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0561P)²+0.3762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.1821(2) 0.3799(2) -0.13422(16) 0.0527(5) Uani 1 1 d . . . . .
H1A H 0.1210 0.4743 -0.1359 0.063 Uiso 1 1 calc R U . . .
H1B H 0.1303 0.3107 -0.0791 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3487(2) 0.39443(18) -0.10254(16) 0.0448(4) Uani 1 1 d . . . . .
H2A H 0.3483 0.3776 -0.0238 0.054 Uiso 1 1 calc R U . . .
H2B H 0.4201 0.3178 -0.1297 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5382(2) 0.5435(2) -0.22955(14) 0.0456(4) Uani 1 1 d . . . . .
H3A H 0.5916 0.4465 -0.2326 0.055 Uiso 1 1 calc R U . . .
H3B H 0.6166 0.6072 -0.2148 0.055 Uiso 1 1 calc R U . . .
C4 C 0.4710(2) 0.6019(2) -0.33727(16) 0.0543(5) Uani 1 1 d . . . . .
H4A H 0.4055 0.6927 -0.3317 0.065 Uiso 1 1 calc R U . . .
H4B H 0.4043 0.5316 -0.3573 0.065 Uiso 1 1 calc R U . . .
C5 C 0.3603(2) 0.65615(18) -0.09252(13) 0.0364(3) Uani 1 1 d . . . . .
C6 C 0.2519(2) 0.64571(18) 0.00006(13) 0.0390(4) Uani 1 1 d . . . . .
H6 H 0.2113 0.5561 0.0270 0.047 Uiso 1 1 calc R U . . .
C7 C 0.2055(2) 0.76582(19) 0.05108(13) 0.0390(4) Uani 1 1 d . . . . .
H7 H 0.1354 0.7547 0.1128 0.047 Uiso 1 1 calc R U . . .
C8 C 0.2597(2) 0.90413(18) 0.01356(13) 0.0370(4) Uani 1 1 d . . . . .
C9 C 0.3671(2) 0.91355(19) -0.07811(14) 0.0442(4) Uani 1 1 d . . . . .
H9 H 0.4072 1.0035 -0.1048 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4159(2) 0.79516(19) -0.13036(14) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.4867 0.8069 -0.1917 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2097(2) 1.03366(19) 0.06425(14) 0.0405(4) Uani 1 1 d . . . . .
H11 H 0.2665 1.1155 0.0402 0.049 Uiso 1 1 calc R U . . .
C12 C 0.0927(2) 1.04989(19) 0.14088(14) 0.0423(4) Uani 1 1 d . . . . .
H12 H 0.0277 0.9736 0.1643 0.051 Uiso 1 1 calc R U . . .
C13 C 0.0642(2) 1.18645(19) 0.18930(14) 0.0415(4) Uani 1 1 d . . . . .
C14 C -0.0284(2) 1.18234(18) 0.29680(14) 0.0397(4) Uani 1 1 d . . . . .
C15 C -0.1195(2) 1.0679(2) 0.34286(16) 0.0489(4) Uani 1 1 d . . . . .
H15 H -0.1283 0.9904 0.3047 0.059 Uiso 1 1 calc R U . . .
C16 C -0.1976(2) 1.0680(2) 0.44529(17) 0.0540(5) Uani 1 1 d . . . . .
H16 H -0.2583 0.9905 0.4746 0.065 Uiso 1 1 calc R U . . .
C17 C -0.1867(2) 1.1810(2) 0.50451(15) 0.0493(4) Uani 1 1 d . . . . .
C18 C -0.0961(2) 1.2951(2) 0.45806(16) 0.0533(5) Uani 1 1 d . . . . .
H18 H -0.0873 1.3725 0.4964 0.064 Uiso 1 1 calc R U . . .
C19 C -0.0190(2) 1.2964(2) 0.35630(15) 0.0476(4) Uani 1 1 d . . . . .
H19 H 0.0403 1.3749 0.3269 0.057 Uiso 1 1 calc R U . . .
C20 C -0.2703(3) 1.1857(3) 0.61637(18) 0.0732(7) Uani 1 1 d . . . . .
H20A H -0.1893 1.1728 0.6688 0.088 Uiso 1 1 calc R U . . .
H20B H -0.3239 1.2829 0.6174 0.088 Uiso 1 1 calc R U . . .
C21 C -0.3889(4) 1.0765(4) 0.6537(2) 0.0969(10) Uani 1 1 d . . . . .
H21A H -0.4677 1.0843 0.6012 0.145 Uiso 1 1 calc R U . . .
H21B H -0.4400 1.0951 0.7225 0.145 Uiso 1 1 calc R U . . .
H21C H -0.3358 0.9794 0.6617 0.145 Uiso 1 1 calc R U . . .
Cl1 Cl 0.63195(8) 0.63482(8) -0.44004(4) 0.0762(2) Uani 1 1 d . . . . .
Cl2 Cl 0.17899(9) 0.31983(7) -0.26319(5) 0.0766(2) Uani 1 1 d . . . . .
N1 N 0.41237(18) 0.53493(16) -0.14207(12) 0.0441(4) Uani 1 1 d . . . . .
O1 O 0.12207(19) 1.29964(14) 0.14569(12) 0.0585(4) 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
C1 C2 1.511(3) . ?
C1 Cl2 1.782(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.451(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.457(2) . ?
C3 C4 1.504(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Cl1 1.802(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.381(2) . ?
C5 C10 1.408(2) . ?
C5 C6 1.409(2) . ?
C6 C7 1.374(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(2) . ?
C8 C11 1.452(2) . ?
C9 C10 1.372(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.331(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.473(2) . ?
C12 H12 0.9300 . ?
C13 O1 1.227(2) . ?
C13 C14 1.492(2) . ?
C14 C15 1.389(2) . ?
C14 C19 1.390(2) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 C20 1.515(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.483(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 C1 Cl2 113.35(14) . . ?
C2 C1 H1A 108.9 . . ?
Cl2 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
Cl2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
N1 C2 C1 115.23(16) . . ?
N1 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N1 C3 C4 110.96(16) . . ?
N1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 Cl1 109.66(14) . . ?
C3 C4 H4A 109.7 . . ?
Cl1 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
Cl1 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N1 C5 C10 121.63(14) . . ?
N1 C5 C6 121.53(14) . . ?
C10 C5 C6 116.82(15) . . ?
C7 C6 C5 121.04(15) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 122.36(15) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
C9 C8 C7 116.25(15) . . ?
C9 C8 C11 120.18(15) . . ?
C7 C8 C11 123.57(15) . . ?
C10 C9 C8 122.53(15) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C5 120.98(15) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C8 128.08(16) . . ?
C12 C11 H11 116.0 . . ?
C8 C11 H11 116.0 . . ?
C11 C12 C13 121.26(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
O1 C13 C12 121.17(16) . . ?
O1 C13 C14 120.18(15) . . ?
C12 C13 C14 118.54(15) . . ?
C15 C14 C19 117.84(16) . . ?
C15 C14 C13 123.61(16) . . ?
C19 C14 C13 118.51(16) . . ?
C16 C15 C14 120.71(17) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 121.22(18) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 117.85(17) . . ?
C16 C17 C20 123.0(2) . . ?
C18 C17 C20 119.18(19) . . ?
C19 C18 C17 121.34(18) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 121.02(18) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C21 C20 C17 117.0(2) . . ?
C21 C20 H20A 108.1 . . ?
C17 C20 H20A 108.1 . . ?
C21 C20 H20B 108.1 . . ?
C17 C20 H20B 108.1 . . ?
H20A C20 H20B 107.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 N1 C2 119.95(14) . . ?
C5 N1 C3 120.90(14) . . ?
C2 N1 C3 119.04(14) . . ?

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
Cl2 C1 C2 N1 86.88(18) . . . . ?
N1 C3 C4 Cl1 172.12(12) . . . . ?
N1 C5 C6 C7 177.56(17) . . . . ?
C10 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 1.2(3) . . . . ?
C6 C7 C8 C9 -1.3(3) . . . . ?
C6 C7 C8 C11 178.48(17) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C11 C8 C9 C10 -178.73(18) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
N1 C5 C10 C9 -177.80(18) . . . . ?
C6 C5 C10 C9 0.6(3) . . . . ?
C9 C8 C11 C12 169.35(18) . . . . ?
C7 C8 C11 C12 -10.4(3) . . . . ?
C8 C11 C12 C13 175.77(17) . . . . ?
C11 C12 C13 O1 16.1(3) . . . . ?
C11 C12 C13 C14 -160.07(17) . . . . ?
O1 C13 C14 C15 168.85(19) . . . . ?
C12 C13 C14 C15 -15.0(3) . . . . ?
O1 C13 C14 C19 -13.5(3) . . . . ?
C12 C13 C14 C19 162.68(17) . . . . ?
C19 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 C16 177.33(18) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C15 C16 C17 C20 179.8(2) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C20 C17 C18 C19 -179.5(2) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C15 C14 C19 C18 0.7(3) . . . . ?
C13 C14 C19 C18 -177.09(18) . . . . ?
C16 C17 C20 C21 -10.4(4) . . . . ?
C18 C17 C20 C21 169.0(2) . . . . ?
C10 C5 N1 C2 -178.24(17) . . . . ?
C6 C5 N1 C2 3.4(3) . . . . ?
C10 C5 N1 C3 5.6(3) . . . . ?
C6 C5 N1 C3 -172.70(16) . . . . ?
C1 C2 N1 C5 76.1(2) . . . . ?
C1 C2 N1 C3 -107.67(19) . . . . ?
C4 C3 N1 C5 -84.2(2) . . . . ?
C4 C3 N1 C2 99.6(2) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and Dichloromethane'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1035426'
_audit_update_record             
;
2014-11-21 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        Chalcone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H23 Cl2 N O3'
_chemical_formula_sum            'C21 H23 Cl2 N O3'
_chemical_formula_weight         408.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   14.8845(4)
_cell_length_b                   16.7875(10)
_cell_length_c                   8.0709(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.708(3)
_cell_angle_gamma                90.00
_cell_volume                     2015.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5902
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      23.54

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_T_max  0.9091
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28756
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3555
_reflns_number_gt                2113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (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)+(0.0546P)²+1.0640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     274
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.62424(18) 0.02218(16) 0.8824(3) 0.0504(7) Uani 1 1 d . A .
C2 C 0.56332(18) 0.07255(16) 0.8013(3) 0.0508(7) Uani 1 1 d . . .
H2 H 0.5126 0.0511 0.7481 0.061 Uiso 1 1 calc R . .
C3 C 0.57673(18) 0.15340(16) 0.7985(3) 0.0528(7) Uani 1 1 d . . .
H3 H 0.5350 0.1851 0.7414 0.063 Uiso 1 1 calc R . .
C4 C 0.64985(18) 0.18965(15) 0.8770(3) 0.0491(7) Uani 1 1 d . . .
C5 C 0.7101(2) 0.13903(18) 0.9575(4) 0.0680(9) Uani 1 1 d . . .
H5 H 0.7602 0.1609 1.0121 0.082 Uiso 1 1 calc R . .
C6 C 0.6989(2) 0.05840(18) 0.9601(4) 0.0694(9) Uani 1 1 d . . .
H6 H 0.7418 0.0269 1.0147 0.083 Uiso 1 1 calc R . .
C7 C 0.66301(19) 0.27505(16) 0.8729(3) 0.0545(7) Uani 1 1 d . . .
H7 H 0.6267 0.3036 0.7983 0.065 Uiso 1 1 calc R . .
C8 C 0.72116(19) 0.31657(16) 0.9642(4) 0.0577(8) Uani 1 1 d . . .
H8 H 0.7587 0.2891 1.0385 0.069 Uiso 1 1 calc R . .
C9 C 0.7300(2) 0.40306(17) 0.9553(4) 0.0552(7) Uani 1 1 d . . .
C10 C 0.80567(18) 0.44480(16) 1.0429(3) 0.0516(7) Uani 1 1 d . . .
C11 C 0.7992(2) 0.52694(17) 1.0551(4) 0.0607(8) Uani 1 1 d . . .
H11 H 0.7487 0.5518 1.0085 0.073 Uiso 1 1 calc R . .
C12 C 0.8633(2) 0.57332(19) 1.1321(4) 0.0721(9) Uani 1 1 d . . .
H12 H 0.8561 0.6282 1.1386 0.087 Uiso 1 1 calc R . .
C13 C 0.9390(2) 0.5369(2) 1.2002(4) 0.0670(9) Uani 1 1 d . . .
C14 C 0.9497(2) 0.45640(19) 1.1897(4) 0.0643(8) Uani 1 1 d . . .
H14 H 1.0012 0.4325 1.2348 0.077 Uiso 1 1 calc R . .
C15 C 0.8837(2) 0.41023(17) 1.1119(4) 0.0613(8) Uani 1 1 d . . .
C16 C 1.0815(2) 0.5533(3) 1.3406(5) 0.1023(13) Uani 1 1 d . . .
H16A H 1.0685 0.5149 1.4248 0.154 Uiso 1 1 calc R . .
H16B H 1.1184 0.5949 1.3876 0.154 Uiso 1 1 calc R . .
H16C H 1.1128 0.5276 1.2530 0.154 Uiso 1 1 calc R . .
C17 C 0.9715(3) 0.2931(3) 1.1663(8) 0.153(2) Uani 1 1 d . . .
H17A H 1.0245 0.3155 1.1199 0.230 Uiso 1 1 calc R . .
H17B H 0.9692 0.2370 1.1433 0.230 Uiso 1 1 calc R . .
H17C H 0.9731 0.3013 1.2840 0.230 Uiso 1 1 calc R . .
C18 C 0.5360(2) -0.09596(17) 0.8027(4) 0.0598(8) Uani 1 1 d . A .
H18A H 0.4824 -0.0662 0.8292 0.072 Uiso 1 1 calc R . .
H18B H 0.5290 -0.1495 0.8455 0.072 Uiso 1 1 calc R . .
C19 C 0.5421(2) -0.10031(16) 0.6172(4) 0.0588(8) Uani 1 1 d . . .
H19A H 0.5648 -0.0500 0.5767 0.071 Uiso 1 1 calc R . .
H19B H 0.4824 -0.1081 0.5687 0.071 Uiso 1 1 calc R . .
N1 N 0.61262(16) -0.05928(13) 0.8864(3) 0.0623(7) Uani 1 1 d D . .
O1 O 0.67390(15) 0.44297(12) 0.8775(3) 0.0778(7) Uani 1 1 d . . .
O2 O 0.89474(16) 0.33034(13) 1.0954(4) 0.1025(9) Uani 1 1 d . . .
O3 O 0.99991(17) 0.58629(15) 1.2760(4) 0.1003(9) Uani 1 1 d . . .
Cl2 Cl 0.61313(6) -0.17845(5) 0.55071(13) 0.0871(3) Uani 1 1 d . . .
C20 C 0.6892(4) -0.1118(3) 0.9377(6) 0.0567(15) Uani 0.646(7) 1 d PDU A 1
H20A H 0.7451 -0.0888 0.9018 0.068 Uiso 0.646(7) 1 calc PR A 1
H20B H 0.6820 -0.1637 0.8863 0.068 Uiso 0.646(7) 1 calc PR A 1
C21 C 0.6917(3) -0.1204(3) 1.1228(6) 0.0635(16) Uani 0.646(7) 1 d PDU A 1
H21A H 0.6383 -0.1482 1.1572 0.076 Uiso 0.646(7) 1 calc PR A 1
H21B H 0.6922 -0.0680 1.1737 0.076 Uiso 0.646(7) 1 calc PR A 1
Cl1 Cl 0.7890(3) -0.1741(3) 1.1903(6) 0.0910(10) Uani 0.646(7) 1 d PDU A 1
C20' C 0.6503(6) -0.1036(5) 1.0319(11) 0.063(3) Uani 0.354(7) 1 d PDU A 2
H20C H 0.6118 -0.1476 1.0615 0.076 Uiso 0.354(7) 1 calc PR A 2
H20D H 0.6590 -0.0688 1.1270 0.076 Uiso 0.354(7) 1 calc PR A 2
C21' C 0.7381(6) -0.1327(7) 0.9700(13) 0.077(3) Uani 0.354(7) 1 d PDU A 2
H21C H 0.7692 -0.0890 0.9178 0.092 Uiso 0.354(7) 1 calc PR A 2
H21D H 0.7272 -0.1737 0.8871 0.092 Uiso 0.354(7) 1 calc PR A 2
Cl1' Cl 0.8068(8) -0.1718(8) 1.1333(13) 0.130(4) Uani 0.354(7) 1 d PDU A 2


_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
C1 N1 1.379(3) . ?
C1 C2 1.389(4) . ?
C1 C6 1.399(4) . ?
C2 C3 1.372(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(4) . ?
C4 C7 1.448(4) . ?
C5 C6 1.364(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.319(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.460(4) . ?
C8 H8 0.9300 . ?
C9 O1 1.228(3) . ?
C9 C10 1.487(4) . ?
C10 C11 1.386(4) . ?
C10 C15 1.399(4) . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9300 . ?
C13 O3 1.360(4) . ?
C13 C14 1.364(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 O2 1.358(3) . ?
C16 O3 1.420(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 O2 1.409(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N1 1.446(3) . ?
C18 C19 1.504(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 Cl2 1.777(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
N1 C20' 1.486(8) . ?
N1 C20 1.489(5) . ?
C20 C21 1.500(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 Cl1 1.778(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20' C21' 1.495(8) . ?
C20' H20C 0.9700 . ?
C20' H20D 0.9700 . ?
C21' Cl1' 1.770(9) . ?
C21' H21C 0.9700 . ?
C21' H21D 0.9700 . ?

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
N1 C1 C2 122.3(2) . . ?
N1 C1 C6 121.3(2) . . ?
C2 C1 C6 116.5(2) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 122.7(2) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 115.8(3) . . ?
C5 C4 C7 122.2(2) . . ?
C3 C4 C7 122.0(2) . . ?
C6 C5 C4 122.7(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C4 126.7(3) . . ?
C8 C7 H7 116.6 . . ?
C4 C7 H7 116.6 . . ?
C7 C8 C9 123.8(3) . . ?
C7 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
O1 C9 C8 120.4(3) . . ?
O1 C9 C10 118.7(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C15 116.3(3) . . ?
C11 C10 C9 116.7(3) . . ?
C15 C10 C9 127.0(3) . . ?
C12 C11 C10 123.4(3) . . ?
C12 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
O3 C13 C14 123.7(3) . . ?
O3 C13 C12 115.7(3) . . ?
C14 C13 C12 120.6(3) . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
O2 C15 C14 120.7(3) . . ?
O2 C15 C10 118.2(3) . . ?
C14 C15 C10 121.1(3) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C19 114.5(2) . . ?
N1 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
N1 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 Cl2 113.0(2) . . ?
C18 C19 H19A 109.0 . . ?
Cl2 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
Cl2 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C1 N1 C18 120.6(2) . . ?
C1 N1 C20' 118.0(4) . . ?
C18 N1 C20' 115.5(4) . . ?
C1 N1 C20 119.8(3) . . ?
C18 N1 C20 117.7(3) . . ?
C20' N1 C20 38.4(4) . . ?
C15 O2 C17 119.8(3) . . ?
C13 O3 C16 118.6(3) . . ?
N1 C20 C21 109.3(4) . . ?
N1 C20 H20A 109.8 . . ?
C21 C20 H20A 109.8 . . ?
N1 C20 H20B 109.8 . . ?
C21 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C20 C21 Cl1 110.5(4) . . ?
C20 C21 H21A 109.5 . . ?
Cl1 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
Cl1 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
N1 C20' C21' 102.3(7) . . ?
N1 C20' H20C 111.3 . . ?
C21' C20' H20C 111.3 . . ?
N1 C20' H20D 111.3 . . ?
C21' C20' H20D 111.3 . . ?
H20C C20' H20D 109.2 . . ?
C20' C21' Cl1' 111.3(9) . . ?
C20' C21' H21C 109.4 . . ?
Cl1' C21' H21C 109.4 . . ?
C20' C21' H21D 109.4 . . ?
Cl1' C21' H21D 109.4 . . ?
H21C C21' H21D 108.0 . . ?

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
N1 C1 C2 C3 -179.6(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C2 C3 C4 C7 -180.0(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C7 C4 C5 C6 -179.1(3) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
N1 C1 C6 C5 -179.4(3) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C5 C4 C7 C8 -12.8(5) . . . . ?
C3 C4 C7 C8 168.2(3) . . . . ?
C4 C7 C8 C9 -179.1(3) . . . . ?
C7 C8 C9 O1 10.6(5) . . . . ?
C7 C8 C9 C10 -170.9(3) . . . . ?
O1 C9 C10 C11 11.0(4) . . . . ?
C8 C9 C10 C11 -167.6(3) . . . . ?
O1 C9 C10 C15 -167.6(3) . . . . ?
C8 C9 C10 C15 13.7(5) . . . . ?
C15 C10 C11 C12 -1.3(5) . . . . ?
C9 C10 C11 C12 179.9(3) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C11 C12 C13 O3 -179.6(3) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
O3 C13 C14 C15 179.2(3) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 O2 177.7(3) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?
C11 C10 C15 O2 -176.8(3) . . . . ?
C9 C10 C15 O2 1.8(5) . . . . ?
C11 C10 C15 C14 0.9(4) . . . . ?
C9 C10 C15 C14 179.6(3) . . . . ?
N1 C18 C19 Cl2 78.0(3) . . . . ?
C2 C1 N1 C18 1.0(4) . . . . ?
C6 C1 N1 C18 -178.8(3) . . . . ?
C2 C1 N1 C20' -150.9(5) . . . . ?
C6 C1 N1 C20' 29.4(6) . . . . ?
C2 C1 N1 C20 165.1(3) . . . . ?
C6 C1 N1 C20 -14.7(5) . . . . ?
C19 C18 N1 C1 75.4(4) . . . . ?
C19 C18 N1 C20' -132.1(5) . . . . ?
C19 C18 N1 C20 -89.1(4) . . . . ?
C14 C15 O2 C17 3.7(6) . . . . ?
C10 C15 O2 C17 -178.6(4) . . . . ?
C14 C13 O3 C16 3.5(5) . . . . ?
C12 C13 O3 C16 -176.6(3) . . . . ?
C1 N1 C20 C21 86.8(4) . . . . ?
C18 N1 C20 C21 -108.6(4) . . . . ?
C20' N1 C20 C21 -11.7(7) . . . . ?
N1 C20 C21 Cl1 -174.0(3) . . . . ?
C1 N1 C20' C21' -97.0(7) . . . . ?
C18 N1 C20' C21' 109.8(7) . . . . ?
C20 N1 C20' C21' 6.7(6) . . . . ?
N1 C20' C21' Cl1' 168.8(7) . . . . ?

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
C8 H8 O2 0.93 2.18 2.773(4) 121.1 .
C17 H17B O3 0.96 2.65 3.526(5) 152.1 2_747
C19 H19B O1 0.97 2.53 3.298(4) 136.3 2_646
C20 H20B Cl2 0.97 2.88 3.476(5) 120.8 .
C20' H20C Cl2 0.97 2.92 3.705(9) 138.5 4_556

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_karthi
_database_code_depnum_ccdc_archive 'CCDC 1061656'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        'Methoxy chalcone'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl2 N O2'
_chemical_formula_weight         378.28

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                   8.3361(3)
_cell_length_b                   9.1285(4)
_cell_length_c                   12.2460(5)
_cell_angle_alpha                81.630(2)
_cell_angle_beta                 84.562(2)
_cell_angle_gamma                83.133(2)
_cell_volume                     912.49(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      29.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.369
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23354
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3209
_reflns_number_gt                2442
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0790P)²+0.8033P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3209
_refine_ls_number_parameters     269
_refine_ls_number_restraints     131
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_restrained_S_all      0.863
_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 0.4675(3) 0.1000(3) -0.3422(2) 0.0513(8) Uani 0.889(5) 1 d D U P A 1
H1A H 0.3937 0.1882 -0.3315 0.062 Uiso 0.889(5) 1 calc R U P A 1
H1B H 0.4069 0.0277 -0.3660 0.062 Uiso 0.889(5) 1 calc R U P A 1
C2 C 0.5394(3) 0.0361(3) -0.2351(2) 0.0448(7) Uani 0.889(5) 1 d D U P A 1
H2A H 0.5930 -0.0631 -0.2408 0.054 Uiso 0.889(5) 1 calc R U P A 1
H2B H 0.6194 0.0979 -0.2200 0.054 Uiso 0.889(5) 1 calc R U P A 1
Cl1 Cl 0.6282(5) 0.1479(4) -0.4468(2) 0.0745(8) Uani 0.889(5) 1 d D U P A 1
C1' C 0.611(2) 0.065(3) -0.3037(17) 0.050(4) Uani 0.111(5) 1 d D U P A 2
H1'1 H 0.6587 -0.0355 -0.3111 0.060 Uiso 0.111(5) 1 calc R U P A 2
H1'2 H 0.6663 0.1040 -0.2496 0.060 Uiso 0.111(5) 1 calc R U P A 2
C2' C 0.434(2) 0.071(3) -0.2731(14) 0.051(4) Uani 0.111(5) 1 d D U P A 2
H2'1 H 0.3868 0.0005 -0.3095 0.061 Uiso 0.111(5) 1 calc R U P A 2
H2'2 H 0.3810 0.1698 -0.2953 0.061 Uiso 0.111(5) 1 calc R U P A 2
Cl1' Cl 0.619(4) 0.182(3) -0.4333(16) 0.063(5) Uani 0.111(5) 1 d D U P A 2
C3 C 0.3500(3) -0.1114(3) -0.1057(2) 0.0486(6) Uani 1 1 d . . . . .
H3A H 0.3516 -0.1294 -0.0258 0.058 Uiso 1 1 calc R U . . .
H3B H 0.4226 -0.1897 -0.1356 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1806(3) -0.1229(3) -0.1351(2) 0.0550(7) Uani 1 1 d . . . . .
H4A H 0.1173 -0.0267 -0.1342 0.066 Uiso 1 1 calc R U . . .
H4B H 0.1300 -0.1935 -0.0793 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3591(3) 0.1519(3) -0.09334(18) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.2537(3) 0.1425(3) 0.00280(19) 0.0426(5) Uani 1 1 d . . . . .
H6 H 0.2150 0.0520 0.0307 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2065(3) 0.2634(3) 0.05653(19) 0.0424(5) Uani 1 1 d . . . . .
H7 H 0.1379 0.2524 0.1210 0.051 Uiso 1 1 calc R U . . .
C8 C 0.2577(3) 0.4028(3) 0.01792(18) 0.0401(5) Uani 1 1 d . . . . .
C9 C 0.3625(3) 0.4113(3) -0.0770(2) 0.0505(6) Uani 1 1 d . . . . .
H9 H 0.4003 0.5023 -0.1048 0.061 Uiso 1 1 calc R U . . .
C10 C 0.4127(3) 0.2913(3) -0.1313(2) 0.0511(6) Uani 1 1 d . . . . .
H10 H 0.4836 0.3025 -0.1946 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2063(3) 0.5330(3) 0.07147(19) 0.0439(5) Uani 1 1 d . . . . .
H11 H 0.2581 0.6170 0.0440 0.053 Uiso 1 1 calc R U . . .
C12 C 0.0951(3) 0.5485(3) 0.1544(2) 0.0476(6) Uani 1 1 d . . . . .
H12 H 0.0351 0.4695 0.1814 0.057 Uiso 1 1 calc R U . . .
C13 C 0.0627(3) 0.6852(3) 0.2054(2) 0.0451(6) Uani 1 1 d . . . . .
C14 C -0.0320(3) 0.6813(3) 0.3140(2) 0.0419(5) Uani 1 1 d . . . . .
C15 C -0.1250(3) 0.5674(3) 0.3580(2) 0.0496(6) Uani 1 1 d . . . . .
H15 H -0.1304 0.4898 0.3175 0.060 Uiso 1 1 calc R U . . .
C16 C -0.2097(3) 0.5665(3) 0.4607(2) 0.0521(6) Uani 1 1 d . . . . .
H16 H -0.2725 0.4897 0.4883 0.063 Uiso 1 1 calc R U . . .
C17 C -0.2006(3) 0.6792(3) 0.5215(2) 0.0505(6) Uani 1 1 d D . . . .
C18 C -0.1059(3) 0.7928(3) 0.4804(2) 0.0543(6) Uani 1 1 d . . . . .
H18 H -0.0972 0.8681 0.5224 0.065 Uiso 1 1 calc R U . . .
C19 C -0.0253(3) 0.7937(3) 0.3778(2) 0.0490(6) Uani 1 1 d . . . . .
H19 H 0.0356 0.8718 0.3501 0.059 Uiso 1 1 calc R U . . .
N1 N 0.4121(2) 0.0294(2) -0.14526(17) 0.0492(5) Uani 1 1 d D U . . .
O1 O 0.1191(2) 0.7996(2) 0.16145(17) 0.0625(5) Uani 1 1 d . . . . .
O2 O -0.2774(13) 0.694(2) 0.6233(6) 0.069(2) Uani 0.84(7) 1 d D U P B 3
C20 C -0.3922(12) 0.591(3) 0.6625(9) 0.071(3) Uani 0.84(7) 1 d D . P B 3
H20A H -0.4743 0.6010 0.6113 0.107 Uiso 0.84(7) 1 calc R U P B 3
H20B H -0.4413 0.6120 0.7336 0.107 Uiso 0.84(7) 1 calc R U P B 3
H20C H -0.3384 0.4919 0.6692 0.107 Uiso 0.84(7) 1 calc R U P B 3
O2' O -0.280(6) 0.660(7) 0.625(2) 0.056(7) Uani 0.16(7) 1 d D U P B 4
C20' C -0.381(7) 0.546(8) 0.666(5) 0.071(3) Uani 0.16(7) 1 d D . P B 4
H20D H -0.4756 0.5590 0.6254 0.107 Uiso 0.16(7) 1 calc R U P B 4
H20E H -0.4125 0.5503 0.7430 0.107 Uiso 0.16(7) 1 calc R U P B 4
H20F H -0.3222 0.4502 0.6577 0.107 Uiso 0.16(7) 1 calc R U P B 4
Cl2 Cl 0.17687(11) -0.18056(9) -0.26702(7) 0.0769(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
C1 C2 1.503(4) . ?
C1 Cl1 1.811(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.454(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1' C2' 1.487(18) . ?
C1' Cl1' 1.778(17) . ?
C1' H1'1 0.9700 . ?
C1' H1'2 0.9700 . ?
C2' N1 1.555(17) . ?
C2' H2'1 0.9700 . ?
C2' H2'2 0.9700 . ?
C3 N1 1.444(3) . ?
C3 C4 1.510(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Cl2 1.775(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.373(3) . ?
C5 C6 1.399(3) . ?
C5 C10 1.400(3) . ?
C6 C7 1.366(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.393(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(3) . ?
C8 C11 1.442(3) . ?
C9 C10 1.366(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.320(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.461(3) . ?
C12 H12 0.9300 . ?
C13 O1 1.227(3) . ?
C13 C14 1.479(3) . ?
C14 C15 1.387(3) . ?
C14 C19 1.386(3) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.368(4) . ?
C16 H16 0.9300 . ?
C17 O2 1.364(5) . ?
C17 O2' 1.368(17) . ?
C17 C18 1.385(4) . ?
C18 C19 1.367(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O2 C20 1.423(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2' C20' 1.423(18) . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 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
C2 C1 Cl1 109.5(2) . . ?
C2 C1 H1A 109.8 . . ?
Cl1 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
Cl1 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N1 C2 C1 109.7(2) . . ?
N1 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2' C1' Cl1' 102.1(16) . . ?
C2' C1' H1'1 111.3 . . ?
Cl1' C1' H1'1 111.3 . . ?
C2' C1' H1'2 111.3 . . ?
Cl1' C1' H1'2 111.3 . . ?
H1'1 C1' H1'2 109.2 . . ?
C1' C2' N1 106.7(15) . . ?
C1' C2' H2'1 110.4 . . ?
N1 C2' H2'1 110.4 . . ?
C1' C2' H2'2 110.4 . . ?
N1 C2' H2'2 110.4 . . ?
H2'1 C2' H2'2 108.6 . . ?
N1 C3 C4 115.2(2) . . ?
N1 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
N1 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 Cl2 112.80(19) . . ?
C3 C4 H4A 109.0 . . ?
Cl2 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
Cl2 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 121.7(2) . . ?
N1 C5 C10 121.7(2) . . ?
C6 C5 C10 116.5(2) . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 122.1(2) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C9 C8 C7 116.2(2) . . ?
C9 C8 C11 120.6(2) . . ?
C7 C8 C11 123.2(2) . . ?
C10 C9 C8 122.6(2) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C5 121.1(2) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C12 C11 C8 128.4(2) . . ?
C12 C11 H11 115.8 . . ?
C8 C11 H11 115.8 . . ?
C11 C12 C13 122.4(2) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
O1 C13 C12 120.7(2) . . ?
O1 C13 C14 120.5(2) . . ?
C12 C13 C14 118.8(2) . . ?
C15 C14 C19 117.3(2) . . ?
C15 C14 C13 123.3(2) . . ?
C19 C14 C13 119.3(2) . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O2 C17 C16 126.4(9) . . ?
C16 C17 O2' 114(3) . . ?
O2 C17 C18 113.5(9) . . ?
C16 C17 C18 120.0(2) . . ?
O2' C17 C18 126(3) . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 121.7(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C5 N1 C3 120.07(19) . . ?
C5 N1 C2 120.9(2) . . ?
C3 N1 C2 118.9(2) . . ?
C5 N1 C2' 111.8(9) . . ?
C3 N1 C2' 116.0(9) . . ?
C17 O2 C20 115.5(10) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 O2' C20' 126(5) . . ?
O2' C20' H20D 109.5 . . ?
O2' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
O2' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 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
Cl1 C1 C2 N1 167.0(2) . . . . ?
Cl1' C1' C2' N1 -157.5(16) . . . . ?
N1 C3 C4 Cl2 86.5(2) . . . . ?
N1 C5 C6 C7 177.4(2) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C8 1.2(4) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C6 C7 C8 C11 178.3(2) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C11 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C5 0.3(4) . . . . ?
N1 C5 C10 C9 -178.1(2) . . . . ?
C6 C5 C10 C9 -0.5(4) . . . . ?
C9 C8 C11 C12 172.1(3) . . . . ?
C7 C8 C11 C12 -7.6(4) . . . . ?
C8 C11 C12 C13 175.9(2) . . . . ?
C11 C12 C13 O1 12.0(4) . . . . ?
C11 C12 C13 C14 -164.7(2) . . . . ?
O1 C13 C14 C15 167.0(2) . . . . ?
C12 C13 C14 C15 -16.2(3) . . . . ?
O1 C13 C14 C19 -15.1(3) . . . . ?
C12 C13 C14 C19 161.7(2) . . . . ?
C19 C14 C15 C16 0.9(4) . . . . ?
C13 C14 C15 C16 178.9(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 O2 179.6(8) . . . . ?
C15 C16 C17 O2' -175(3) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
O2 C17 C18 C19 -178.4(7) . . . . ?
C16 C17 C18 C19 1.8(4) . . . . ?
O2' C17 C18 C19 176(3) . . . . ?
C17 C18 C19 C14 -1.7(4) . . . . ?
C15 C14 C19 C18 0.4(4) . . . . ?
C13 C14 C19 C18 -177.7(2) . . . . ?
C6 C5 N1 C3 4.6(3) . . . . ?
C10 C5 N1 C3 -178.0(2) . . . . ?
C6 C5 N1 C2 -170.9(2) . . . . ?
C10 C5 N1 C2 6.5(4) . . . . ?
C6 C5 N1 C2' 145.5(8) . . . . ?
C10 C5 N1 C2' -37.0(9) . . . . ?
C4 C3 N1 C5 75.8(3) . . . . ?
C4 C3 N1 C2 -108.7(3) . . . . ?
C4 C3 N1 C2' -63.7(9) . . . . ?
C1 C2 N1 C5 -83.5(3) . . . . ?
C1 C2 N1 C3 101.0(3) . . . . ?
C1 C2 N1 C2' 4.1(14) . . . . ?
C1' C2' N1 C5 105.7(16) . . . . ?
C1' C2' N1 C3 -111.6(15) . . . . ?
C1' C2' N1 C2 -6.9(10) . . . . ?
C16 C17 O2 C20 -8.0(13) . . . . ?
O2' C17 O2 C20 -28(12) . . . . ?
C18 C17 O2 C20 172.2(7) . . . . ?
O2 C17 O2' C20' 155(17) . . . . ?
C16 C17 O2' C20' -7(6) . . . . ?
C18 C17 O2' C20' 178(4) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.039

_shelxl_version_number           2012-9


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_BrC
_database_code_depnum_ccdc_archive 'CCDC 1402531'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(4-(bis(2-chloroethyl)amino)phenyl)-1-(4-bromophenyl)prop-2-en-1-one
_chemical_name_common            'Bromo chalcone'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Br Cl2 N O'
_chemical_formula_weight         427.15

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'
Br Br -0.2901 2.4595 '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                   8.0990(2)
_cell_length_b                   9.3548(2)
_cell_length_c                   12.8639(4)
_cell_angle_alpha                75.6264(12)
_cell_angle_beta                 79.1564(13)
_cell_angle_gamma                79.0160(13)
_cell_volume                     916.60(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5719
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.00

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    2.539
_shelx_estimated_absorpt_T_min   0.497
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.702
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13241
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_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             3231
_reflns_number_gt                2524
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0212P)²+0.9150P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3231
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
Br1 Br 1.36809(5) -0.12130(5) 0.36259(3) 0.08695(17) Uani 1 1 d . . . . .
C1 C 1.1429(4) -0.0271(3) 0.6576(2) 0.0580(8) Uani 1 1 d . . . . .
H1 H 1.1453 0.0450 0.6955 0.070 Uiso 1 1 calc R U . . .
C2 C 1.2399(4) -0.0217(4) 0.5567(3) 0.0621(8) Uani 1 1 d . . . . .
H2 H 1.3082 0.0522 0.5272 0.075 Uiso 1 1 calc R U . . .
C3 C 1.2340(4) -0.1264(3) 0.5010(2) 0.0534(7) Uani 1 1 d . . . . .
C4 C 1.1353(4) -0.2364(4) 0.5432(3) 0.0634(8) Uani 1 1 d . . . . .
H4 H 1.1315 -0.3065 0.5039 0.076 Uiso 1 1 calc R U . . .
C5 C 1.0410(4) -0.2419(3) 0.6451(2) 0.0554(7) Uani 1 1 d . . . . .
H5 H 0.9756 -0.3179 0.6748 0.066 Uiso 1 1 calc R U . . .
C6 C 1.0419(3) -0.1372(3) 0.7037(2) 0.0442(6) Uani 1 1 d . . . . .
C7 C 0.9335(4) -0.1485(3) 0.8127(2) 0.0489(7) Uani 1 1 d . . . . .
C8 C 0.8947(4) -0.0178(3) 0.8615(2) 0.0512(7) Uani 1 1 d . . . . .
H8 H 0.9539 0.0621 0.8304 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7790(3) -0.0091(3) 0.9479(2) 0.0482(7) Uani 1 1 d . . . . .
H9 H 0.7255 -0.0927 0.9780 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7252(3) 0.1150(3) 1.0015(2) 0.0432(6) Uani 1 1 d . . . . .
C11 C 0.6140(4) 0.1015(3) 1.0990(2) 0.0531(7) Uani 1 1 d . . . . .
H11 H 0.5727 0.0116 1.1289 0.064 Uiso 1 1 calc R U . . .
C12 C 0.5633(4) 0.2158(3) 1.1524(2) 0.0551(8) Uani 1 1 d . . . . .
H12 H 0.4887 0.2018 1.2173 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6219(3) 0.3538(3) 1.1108(2) 0.0466(6) Uani 1 1 d . . . . .
C14 C 0.7330(3) 0.3685(3) 1.0120(2) 0.0462(6) Uani 1 1 d . . . . .
H14 H 0.7745 0.4582 0.9816 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7811(3) 0.2529(3) 0.9599(2) 0.0462(6) Uani 1 1 d . . . . .
H15 H 0.8538 0.2669 0.8942 0.055 Uiso 1 1 calc R U . . .
C16 C 0.4179(9) 0.4734(6) 1.2435(6) 0.048(2) Uani 0.623(15) 1 d . . P A 1
H16A H 0.3406 0.4147 1.2302 0.058 Uiso 0.623(15) 1 calc R U P A 1
H16B H 0.3605 0.5750 1.2401 0.058 Uiso 0.623(15) 1 calc R U P A 1
C17 C 0.4758(9) 0.4070(7) 1.3536(7) 0.063(2) Uani 0.623(15) 1 d . . P A 1
H17A H 0.5475 0.4689 1.3691 0.076 Uiso 0.623(15) 1 calc R U P A 1
H17B H 0.5388 0.3073 1.3559 0.076 Uiso 0.623(15) 1 calc R U P A 1
C17A C 0.3303(15) 0.4596(10) 1.3041(10) 0.061(4) Uani 0.372(15) 1 d . . P A 2
H17C H 0.2865 0.3998 1.2669 0.073 Uiso 0.372(15) 1 calc R U P A 2
H17D H 0.2887 0.5644 1.2778 0.073 Uiso 0.372(15) 1 calc R U P A 2
C16A C 0.5186(15) 0.4302(11) 1.2925(11) 0.050(3) Uani 0.372(15) 1 d . . P A 2
H16C H 0.5590 0.3265 1.3231 0.061 Uiso 0.372(15) 1 calc R U P A 2
H16D H 0.5617 0.4936 1.3271 0.061 Uiso 0.372(15) 1 calc R U P A 2
C18 C 0.6369(4) 0.6106(3) 1.1177(2) 0.0547(7) Uani 1 1 d . . . . .
H18A H 0.5639 0.6874 1.1507 0.066 Uiso 1 1 calc R U . . .
H18B H 0.6296 0.6379 1.0407 0.066 Uiso 1 1 calc R U . . .
C19 C 0.8184(4) 0.6091(3) 1.1324(2) 0.0548(7) Uani 1 1 d . . . . .
H19A H 0.8689 0.6823 1.0736 0.066 Uiso 1 1 calc R U . . .
H19B H 0.8832 0.5116 1.1282 0.066 Uiso 1 1 calc R U . . .
Cl2 Cl 0.83276(13) 0.64911(11) 1.25868(7) 0.0803(3) Uani 1 1 d . . . . .
N1 N 0.5729(3) 0.4702(3) 1.1636(2) 0.0603(7) Uani 1 1 d . . . . .
O1 O 0.8749(3) -0.2639(2) 0.85691(17) 0.0666(6) Uani 1 1 d . . . . .
Cl1 Cl 0.27648(16) 0.40158(12) 1.45242(7) 0.0984(4) 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
Br1 C3 1.898(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.499(4) . ?
C7 O1 1.225(3) . ?
C7 C8 1.465(4) . ?
C8 C9 1.321(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.451(4) . ?
C9 H9 0.9300 . ?
C10 C15 1.395(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.405(4) . ?
C12 H12 0.9300 . ?
C13 N1 1.381(3) . ?
C13 C14 1.405(4) . ?
C14 C15 1.368(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N1 1.466(8) . ?
C16 C17 1.521(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 Cl1 1.858(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17A C16A 1.482(19) . ?
C17A Cl1 1.840(12) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C16A N1 1.601(14) . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C18 N1 1.450(3) . ?
C18 C19 1.513(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 Cl2 1.784(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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
C2 C1 C6 121.6(3) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 Br1 119.2(2) . . ?
C2 C3 Br1 119.4(2) . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 118.4(2) . . ?
C1 C6 C7 124.0(3) . . ?
O1 C7 C8 121.7(3) . . ?
O1 C7 C6 119.6(3) . . ?
C8 C7 C6 118.6(2) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 127.9(3) . . ?
C8 C9 H9 116.1 . . ?
C10 C9 H9 116.1 . . ?
C15 C10 C11 116.2(2) . . ?
C15 C10 C9 122.7(2) . . ?
C11 C10 C9 121.0(2) . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N1 C13 C12 122.0(2) . . ?
N1 C13 C14 121.2(2) . . ?
C12 C13 C14 116.8(3) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 122.5(2) . . ?
C14 C15 H15 118.8 . . ?
C10 C15 H15 118.8 . . ?
N1 C16 C17 105.8(6) . . ?
N1 C16 H16A 110.6 . . ?
C17 C16 H16A 110.6 . . ?
N1 C16 H16B 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
C16 C17 Cl1 105.0(5) . . ?
C16 C17 H17A 110.8 . . ?
Cl1 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
Cl1 C17 H17B 110.8 . . ?
H17A C17 H17B 108.8 . . ?
C16A C17A Cl1 100.3(8) . . ?
C16A C17A H17C 111.7 . . ?
Cl1 C17A H17C 111.7 . . ?
C16A C17A H17D 111.7 . . ?
Cl1 C17A H17D 111.7 . . ?
H17C C17A H17D 109.5 . . ?
C17A C16A N1 102.5(10) . . ?
C17A C16A H16C 111.3 . . ?
N1 C16A H16C 111.3 . . ?
C17A C16A H16D 111.3 . . ?
N1 C16A H16D 111.3 . . ?
H16C C16A H16D 109.2 . . ?
N1 C18 C19 114.7(3) . . ?
N1 C18 H18A 108.6 . . ?
C19 C18 H18A 108.6 . . ?
N1 C18 H18B 108.6 . . ?
C19 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
C18 C19 Cl2 112.7(2) . . ?
C18 C19 H19A 109.0 . . ?
Cl2 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
Cl2 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C13 N1 C18 120.1(2) . . ?
C13 N1 C16 120.0(3) . . ?
C18 N1 C16 116.8(3) . . ?
C13 N1 C16A 117.9(4) . . ?
C18 N1 C16A 116.6(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
C6 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C1 C2 C3 Br1 -179.5(2) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
Br1 C3 C4 C5 178.4(2) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?
C4 C5 C6 C1 -1.0(4) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 O1 14.8(4) . . . . ?
C1 C6 C7 O1 -165.6(3) . . . . ?
C5 C6 C7 C8 -162.7(3) . . . . ?
C1 C6 C7 C8 16.9(4) . . . . ?
O1 C7 C8 C9 -8.8(5) . . . . ?
C6 C7 C8 C9 168.7(3) . . . . ?
C7 C8 C9 C10 -177.8(3) . . . . ?
C8 C9 C10 C15 6.5(5) . . . . ?
C8 C9 C10 C11 -173.1(3) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
C9 C10 C11 C12 178.9(3) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 N1 -179.7(3) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
N1 C13 C14 C15 -179.9(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C10 -0.7(4) . . . . ?
C11 C10 C15 C14 1.2(4) . . . . ?
C9 C10 C15 C14 -178.5(3) . . . . ?
N1 C16 C17 Cl1 -176.6(3) . . . . ?
Cl1 C17A C16A N1 176.9(4) . . . . ?
N1 C18 C19 Cl2 -86.4(3) . . . . ?
C12 C13 N1 C18 179.9(3) . . . . ?
C14 C13 N1 C18 -0.4(4) . . . . ?
C12 C13 N1 C16 -20.4(5) . . . . ?
C14 C13 N1 C16 159.2(4) . . . . ?
C12 C13 N1 C16A 26.6(6) . . . . ?
C14 C13 N1 C16A -153.7(5) . . . . ?
C19 C18 N1 C13 -76.6(4) . . . . ?
C19 C18 N1 C16 123.1(4) . . . . ?
C19 C18 N1 C16A 77.0(5) . . . . ?
C17 C16 N1 C13 96.2(5) . . . . ?
C17 C16 N1 C18 -103.5(4) . . . . ?
C17A C16A N1 C13 -101.3(6) . . . . ?
C17A C16A N1 C18 104.5(6) . . . . ?

_refine_diff_density_max         0.466
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol and dichloromethane'
####################################################################### 
# 
# 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_MC1
_database_code_depnum_ccdc_archive 'CCDC 1042842'
_audit_update_record             
;
2015-01-09 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Chalcone
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 Cl2 N O'
_chemical_formula_sum            'C20 H21 Cl2 N O'
_chemical_formula_weight         362.28

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                   8.1897(4)
_cell_length_b                   9.3642(4)
_cell_length_c                   12.3569(6)
_cell_angle_alpha                77.946(2)
_cell_angle_beta                 81.053(2)
_cell_angle_gamma                83.095(3)
_cell_volume                     911.70(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6626
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      24.39

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8812
_exptl_absorpt_correction_T_max  0.9012
_exptl_absorpt_process_details   'SADABS (BRUKER, 2004)'
_exptl_absorpt_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 axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20979
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_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             3215
_reflns_number_gt                2091
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'




_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)+(0.0552P)²+0.3445P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3215
_refine_ls_number_parameters     281
_refine_ls_number_restraints     283
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.006
_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 1.3368(5) -0.1414(5) -0.6327(3) 0.1192(14) Uani 1 1 d . . . . .
H1A H 1.3187 -0.2240 -0.6626 0.179 Uiso 1 1 calc R U . . .
H1B H 1.3044 -0.0524 -0.6820 0.179 Uiso 1 1 calc R U . . .
H1C H 1.4523 -0.1444 -0.6255 0.179 Uiso 1 1 calc R U . . .
C2 C 1.2349(4) -0.1467(4) -0.5196(3) 0.0788(9) Uani 1 1 d . . . . .
C3 C 1.1349(4) -0.2573(4) -0.4741(3) 0.0838(9) Uani 1 1 d . . . . .
H3 H 1.1282 -0.3290 -0.5147 0.101 Uiso 1 1 calc R U . . .
C4 C 1.0439(4) -0.2650(3) -0.3698(3) 0.0690(8) Uani 1 1 d . . . . .
H4 H 0.9794 -0.3429 -0.3406 0.083 Uiso 1 1 calc R U . . .
C5 C 1.0474(3) -0.1584(3) -0.3077(2) 0.0566(6) Uani 1 1 d . . . . .
C6 C 1.1465(4) -0.0459(3) -0.3552(3) 0.0709(8) Uani 1 1 d . . . . .
H6 H 1.1515 0.0282 -0.3164 0.085 Uiso 1 1 calc R U . . .
C7 C 1.2381(4) -0.0420(3) -0.4592(3) 0.0819(9) Uani 1 1 d . . . . .
H7 H 1.3041 0.0348 -0.4887 0.098 Uiso 1 1 calc R U . . .
C8 C 0.9439(3) -0.1688(3) -0.1976(2) 0.0561(6) Uani 1 1 d . . . . .
C9 C 0.9084(3) -0.0386(3) -0.1469(2) 0.0575(7) Uani 1 1 d . . . . .
H9 H 0.9716 0.0404 -0.1757 0.069 Uiso 1 1 calc R U . . .
C10 C 0.7907(3) -0.0283(3) -0.0623(2) 0.0544(6) Uani 1 1 d . . . . .
H10 H 0.7350 -0.1116 -0.0328 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7377(3) 0.0965(2) -0.0097(2) 0.0489(6) Uani 1 1 d . . . . .
C12 C 0.6251(3) 0.0851(3) 0.0868(2) 0.0559(6) Uani 1 1 d . . . . .
H12 H 0.5832 -0.0048 0.1172 0.067 Uiso 1 1 calc R U . . .
C13 C 0.5728(3) 0.2006(3) 0.1393(2) 0.0579(7) Uani 1 1 d . . . . .
H13 H 0.4972 0.1873 0.2042 0.069 Uiso 1 1 calc R U . . .
C14 C 0.6313(3) 0.3385(2) 0.09682(19) 0.0485(6) Uani 1 1 d D . . . .
C15 C 0.7460(3) 0.3502(3) -0.0002(2) 0.0501(6) Uani 1 1 d . . . . .
H15 H 0.7898 0.4393 -0.0304 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7951(3) 0.2337(3) -0.0517(2) 0.0507(6) Uani 1 1 d . . . . .
H16 H 0.8695 0.2466 -0.1172 0.061 Uiso 1 1 calc R U . . .
O1 O 0.8826(3) -0.2834(2) -0.15259(17) 0.0739(6) Uani 1 1 d . . . . .
C17 C 0.4412(4) 0.4504(3) 0.2369(2) 0.0513(9) Uani 0.836(5) 1 d D U P A 1
H17A H 0.3616 0.3867 0.2273 0.062 Uiso 0.836(5) 1 calc R U P A 1
H17B H 0.3837 0.5469 0.2382 0.062 Uiso 0.836(5) 1 calc R U P A 1
C18 C 0.5063(5) 0.3920(4) 0.3462(3) 0.0634(10) Uani 0.836(5) 1 d D U P A 1
H18A H 0.5792 0.4593 0.3591 0.076 Uiso 0.836(5) 1 calc R U P A 1
H18B H 0.5700 0.2982 0.3437 0.076 Uiso 0.836(5) 1 calc R U P A 1
C19 C 0.6439(8) 0.5981(5) 0.0991(4) 0.0509(11) Uani 0.836(5) 1 d D U P A 1
H19A H 0.5691 0.6752 0.1263 0.061 Uiso 0.836(5) 1 calc R U P A 1
H19B H 0.6492 0.6175 0.0185 0.061 Uiso 0.836(5) 1 calc R U P A 1
C20 C 0.8139(7) 0.6086(7) 0.1270(4) 0.0556(16) Uani 0.836(5) 1 d D U P A 1
H20A H 0.8691 0.6790 0.0678 0.067 Uiso 0.836(5) 1 calc R U P A 1
H20B H 0.8771 0.5141 0.1270 0.067 Uiso 0.836(5) 1 calc R U P A 1
N1 N 0.5722(4) 0.4600(3) 0.1432(3) 0.0487(9) Uani 0.836(5) 1 d D U P A 1
Cl1 Cl 0.3396(5) 0.3706(5) 0.4562(2) 0.0894(8) Uani 0.836(5) 1 d D U P A 1
Cl2 Cl 0.8215(6) 0.6606(4) 0.2571(2) 0.0884(11) Uani 0.836(5) 1 d D U P A 1
C17' C 0.5405(18) 0.408(2) 0.2889(13) 0.055(4) Uani 0.164(5) 1 d D U P A 2
H17C H 0.5853 0.4723 0.3265 0.065 Uiso 0.164(5) 1 calc R U P A 2
H17D H 0.5741 0.3076 0.3231 0.065 Uiso 0.164(5) 1 calc R U P A 2
Cl2' Cl 0.790(3) 0.678(2) 0.2545(13) 0.076(3) Uani 0.164(5) 1 d D U P A 2
Cl1' Cl 0.295(3) 0.400(2) 0.4543(13) 0.101(6) Uani 0.164(5) 1 d D U P A 2
C18' C 0.3542(18) 0.431(2) 0.3075(13) 0.067(4) Uani 0.164(5) 1 d D U P A 2
H18C H 0.3058 0.3634 0.2749 0.080 Uiso 0.164(5) 1 calc R U P A 2
H18D H 0.3171 0.5306 0.2736 0.080 Uiso 0.164(5) 1 calc R U P A 2
C19' C 0.657(4) 0.582(2) 0.128(3) 0.058(5) Uani 0.164(5) 1 d D U P A 2
H19C H 0.5872 0.6505 0.1682 0.069 Uiso 0.164(5) 1 calc R U P A 2
H19D H 0.6423 0.6107 0.0493 0.069 Uiso 0.164(5) 1 calc R U P A 2
C20' C 0.835(4) 0.582(4) 0.142(3) 0.056(6) Uani 0.164(5) 1 d D U P A 2
H20C H 0.8996 0.6364 0.0769 0.067 Uiso 0.164(5) 1 calc R U P A 2
H20D H 0.8891 0.4845 0.1632 0.067 Uiso 0.164(5) 1 calc R U P A 2
N1' N 0.613(3) 0.4335(16) 0.1719(11) 0.051(4) Uani 0.164(5) 1 d D U P A 2


_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
C1 C2 1.506(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.356(4) . ?
C2 C3 1.370(5) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(4) . ?
C5 C8 1.478(4) . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.227(3) . ?
C8 C9 1.464(3) . ?
C9 C10 1.319(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.444(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.367(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.400(3) . ?
C13 H13 0.9300 . ?
C14 N1 1.383(3) . ?
C14 N1' 1.395(9) . ?
C14 C15 1.397(3) . ?
C15 C16 1.364(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.447(4) . ?
C17 C18 1.501(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 Cl1 1.769(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N1 1.450(4) . ?
C19 C20 1.504(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 Cl2 1.787(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C17' N1' 1.457(8) . ?
C17' C18' 1.504(9) . ?
C17' H17C 0.9700 . ?
C17' H17D 0.9700 . ?
Cl2' C20' 1.777(9) . ?
Cl1' C18' 1.775(9) . ?
C18' H18C 0.9700 . ?
C18' H18D 0.9700 . ?
C19' N1' 1.453(8) . ?
C19' C20' 1.502(9) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C20' H20C 0.9700 . ?
C20' H20D 0.9700 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.4(3) . . ?
C7 C2 C1 121.3(4) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 C8 124.1(2) . . ?
C4 C5 C8 119.0(2) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C2 C7 C6 122.0(3) . . ?
C2 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
O1 C8 C9 120.9(2) . . ?
O1 C8 C5 120.0(2) . . ?
C9 C8 C5 119.0(2) . . ?
C10 C9 C8 122.8(2) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C11 128.0(2) . . ?
C9 C10 H10 116.0 . . ?
C11 C10 H10 116.0 . . ?
C12 C11 C16 116.1(2) . . ?
C12 C11 C10 121.0(2) . . ?
C16 C11 C10 122.9(2) . . ?
C13 C12 C11 122.7(2) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
N1 C14 C15 120.9(2) . . ?
N1' C14 C15 124.2(8) . . ?
N1 C14 C13 122.5(2) . . ?
N1' C14 C13 115.9(7) . . ?
C15 C14 C13 116.5(2) . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 122.3(2) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
N1 C17 C18 112.1(3) . . ?
N1 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N1 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 Cl1 110.0(3) . . ?
C17 C18 H18A 109.7 . . ?
Cl1 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
Cl1 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 C20 116.6(4) . . ?
N1 C19 H19A 108.2 . . ?
C20 C19 H19A 108.2 . . ?
N1 C19 H19B 108.2 . . ?
C20 C19 H19B 108.2 . . ?
H19A C19 H19B 107.3 . . ?
C19 C20 Cl2 116.3(4) . . ?
C19 C20 H20A 108.2 . . ?
Cl2 C20 H20A 108.2 . . ?
C19 C20 H20B 108.2 . . ?
Cl2 C20 H20B 108.2 . . ?
H20A C20 H20B 107.4 . . ?
C14 N1 C17 120.6(3) . . ?
C14 N1 C19 119.9(4) . . ?
C17 N1 C19 119.4(3) . . ?
N1' C17' C18' 114.4(16) . . ?
N1' C17' H17C 108.7 . . ?
C18' C17' H17C 108.7 . . ?
N1' C17' H17D 108.7 . . ?
C18' C17' H17D 108.7 . . ?
H17C C17' H17D 107.6 . . ?
C17' C18' Cl1' 106.4(13) . . ?
C17' C18' H18C 110.4 . . ?
Cl1' C18' H18C 110.5 . . ?
C17' C18' H18D 110.4 . . ?
Cl1' C18' H18D 110.4 . . ?
H18C C18' H18D 108.6 . . ?
N1' C19' C20' 106(3) . . ?
N1' C19' H19C 110.5 . . ?
C20' C19' H19C 110.5 . . ?
N1' C19' H19D 110.5 . . ?
C20' C19' H19D 110.5 . . ?
H19C C19' H19D 108.7 . . ?
C19' C20' Cl2' 94.3(18) . . ?
C19' C20' H20C 112.9 . . ?
Cl2' C20' H20C 112.9 . . ?
C19' C20' H20D 112.9 . . ?
Cl2' C20' H20D 112.9 . . ?
H20C C20' H20D 110.3 . . ?
C14 N1' C19' 117.1(18) . . ?
C14 N1' C17' 128.3(13) . . ?
C19' N1' C17' 114.3(17) . . ?

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 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 C4 178.6(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C8 178.2(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C8 C5 C6 C7 -179.0(3) . . . . ?
C3 C2 C7 C6 0.7(5) . . . . ?
C1 C2 C7 C6 -179.5(3) . . . . ?
C5 C6 C7 C2 0.3(5) . . . . ?
C6 C5 C8 O1 -167.2(3) . . . . ?
C4 C5 C8 O1 14.2(4) . . . . ?
C6 C5 C8 C9 16.3(4) . . . . ?
C4 C5 C8 C9 -162.2(2) . . . . ?
O1 C8 C9 C10 -11.3(4) . . . . ?
C5 C8 C9 C10 165.1(2) . . . . ?
C8 C9 C10 C11 -176.1(2) . . . . ?
C9 C10 C11 C12 -172.5(3) . . . . ?
C9 C10 C11 C16 7.6(4) . . . . ?
C16 C11 C12 C13 -0.5(4) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 N1 175.3(3) . . . . ?
C12 C13 C14 N1' -160.7(10) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
N1 C14 C15 C16 -174.7(3) . . . . ?
N1' C14 C15 C16 159.5(10) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C14 C15 C16 C11 -1.6(4) . . . . ?
C12 C11 C16 C15 1.1(4) . . . . ?
C10 C11 C16 C15 -178.9(2) . . . . ?
N1 C17 C18 Cl1 -175.9(3) . . . . ?
N1 C19 C20 Cl2 -85.6(6) . . . . ?
C15 C14 N1 C17 173.6(3) . . . . ?
C13 C14 N1 C17 -2.2(5) . . . . ?
C15 C14 N1 C19 -7.5(5) . . . . ?
C13 C14 N1 C19 176.7(3) . . . . ?
C18 C17 N1 C14 83.1(4) . . . . ?
C18 C17 N1 C19 -95.8(4) . . . . ?
C20 C19 N1 C14 -73.7(5) . . . . ?
C20 C19 N1 C17 105.2(5) . . . . ?
N1' C17' C18' Cl1' -177.9(14) . . . . ?
N1' C19' C20' Cl2' -106(3) . . . . ?
C15 C14 N1' C19' 28(2) . . . . ?
C13 C14 N1' C19' -173.8(17) . . . . ?
C15 C14 N1' C17' -158.4(15) . . . . ?
C13 C14 N1' C17' 0(2) . . . . ?
C20' C19' N1' C14 -92(2) . . . . ?
C20' C19' N1' C17' 93(3) . . . . ?
C18' C17' N1' C14 -82(2) . . . . ?
C18' C17' N1' C19' 92(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
C18 H18A Cl2 0.97 2.86 3.704(5) 145.3 .
C20 H20A O1 0.97 2.66 3.369(6) 130.3 1_565
C17' H17C Cl2' 0.97 2.63 3.36(2) 132.4 .
C18' H18C O1 0.97 2.59 3.500(16) 156.5 2_655
C20' H20D O1 0.97 2.50 3.40(3) 155.1 2_755

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_nc
_database_code_depnum_ccdc_archive 'CCDC 1426151'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(E)-3-(4-(bis(2-chloroethyl)amino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one
_chemical_name_common            Nitrochalcone
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cl2 N2 O3'
_chemical_formula_weight         393.25

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                   8.0622(5)
_cell_length_b                   9.3324(6)
_cell_length_c                   12.5869(8)
_cell_angle_alpha                78.365(3)
_cell_angle_beta                 81.741(4)
_cell_angle_gamma                81.832(4)
_cell_volume                     911.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5690
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.87

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.378
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11309
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.664
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11309
_reflns_number_gt                8855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1180P)²+1.1627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11309
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.2187
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.002
_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 0.6781(6) 0.3904(5) -0.1325(4) 0.0501(12) Uani 1 1 d . . . . .
H1A H 0.6147 0.4853 -0.1261 0.060 Uiso 1 1 calc R U . . .
H1B H 0.6292 0.3169 -0.0753 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8586(6) 0.3943(5) -0.1156(4) 0.0476(11) Uani 1 1 d . . . . .
H2A H 0.8684 0.3677 -0.0380 0.057 Uiso 1 1 calc R U . . .
H2B H 0.9296 0.3202 -0.1509 0.057 Uiso 1 1 calc R U . . .
C3 C 1.0685(8) 0.5439(6) -0.2476(5) 0.0748(17) Uani 1 1 d . . . . .
H3A H 1.1451 0.6106 -0.2384 0.090 Uiso 1 1 calc R U . . .
H3B H 1.1306 0.4474 -0.2500 0.090 Uiso 1 1 calc R U . . .
C4 C 0.9874(8) 0.5980(7) -0.3424(5) 0.0829(19) Uani 1 1 d . . . . .
H4A H 0.9182 0.6908 -0.3369 0.099 Uiso 1 1 calc R U . . .
H4B H 0.9166 0.5279 -0.3537 0.099 Uiso 1 1 calc R U . . .
C5 C 0.8718(5) 0.6536(4) -0.1043(3) 0.0388(10) Uani 1 1 d . . . . .
C6 C 0.7658(5) 0.6384(5) -0.0049(3) 0.0401(10) Uani 1 1 d . . . . .
H6 H 0.7272 0.5480 0.0252 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7183(5) 0.7551(5) 0.0485(3) 0.0403(10) Uani 1 1 d . . . . .
H7 H 0.6500 0.7411 0.1150 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7696(5) 0.8943(5) 0.0058(3) 0.0379(10) Uani 1 1 d . . . . .
C9 C 0.8752(5) 0.9080(5) -0.0927(3) 0.0441(11) Uani 1 1 d . . . . .
H9 H 0.9132 0.9987 -0.1230 0.053 Uiso 1 1 calc R U . . .
C10 C 0.9245(6) 0.7926(5) -0.1462(3) 0.0466(11) Uani 1 1 d . . . . .
H10 H 0.9948 0.8068 -0.2119 0.056 Uiso 1 1 calc R U . . .
C11 C 0.7158(5) 1.0198(5) 0.0599(3) 0.0410(10) Uani 1 1 d . . . . .
H11 H 0.7673 1.1044 0.0301 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6028(5) 1.0284(5) 0.1462(3) 0.0451(11) Uani 1 1 d . . . . .
H12 H 0.5461 0.9470 0.1771 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5631(5) 1.1605(5) 0.1951(3) 0.0438(11) Uani 1 1 d . . . . .
C14 C 0.4587(5) 1.1496(5) 0.3050(3) 0.0403(10) Uani 1 1 d . . . . .
C15 C 0.3579(6) 1.0391(5) 0.3475(4) 0.0493(12) Uani 1 1 d . . . . .
H15 H 0.3513 0.9679 0.3066 0.059 Uiso 1 1 calc R U . . .
C16 C 0.2661(6) 1.0323(5) 0.4499(4) 0.0522(12) Uani 1 1 d . . . . .
H16 H 0.1973 0.9582 0.4778 0.063 Uiso 1 1 calc R U . . .
C17 C 0.2794(6) 1.1372(5) 0.5090(3) 0.0464(12) Uani 1 1 d . . . . .
C18 C 0.3788(6) 1.2487(5) 0.4701(4) 0.0521(12) Uani 1 1 d . . . . .
H18 H 0.3861 1.3185 0.5121 0.063 Uiso 1 1 calc R U . . .
C19 C 0.4678(6) 1.2551(5) 0.3672(4) 0.0480(11) Uani 1 1 d . . . . .
H19 H 0.5346 1.3308 0.3392 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 1.1686(2) 0.62475(17) -0.45995(10) 0.0832(6) Uani 1 1 d . . . . .
Cl2 Cl 0.6578(2) 0.34883(17) -0.26273(11) 0.0759(5) Uani 1 1 d . . . . .
N1 N 0.9221(5) 0.5360(4) -0.1574(3) 0.0523(10) Uani 1 1 d . . . . .
N2 N 0.1835(6) 1.1319(5) 0.6185(3) 0.0644(13) Uani 1 1 d . . . . .
O1 O 0.6177(4) 1.2778(4) 0.1513(3) 0.0574(9) Uani 1 1 d . . . . .
O2 O 0.0910(7) 1.0340(6) 0.6504(3) 0.1041(16) Uani 1 1 d . . . . .
O3 O 0.1983(7) 1.2220(5) 0.6721(3) 0.0971(16) 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
C1 C2 1.507(6) . ?
C1 Cl2 1.794(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.457(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.413(7) . ?
C3 N1 1.514(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 Cl1 1.929(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N1 1.381(5) . ?
C5 C10 1.400(6) . ?
C5 C6 1.404(5) . ?
C6 C7 1.374(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(6) . ?
C8 C11 1.454(6) . ?
C9 C10 1.366(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.322(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.462(6) . ?
C12 H12 0.9300 . ?
C13 O1 1.233(5) . ?
C13 C14 1.505(6) . ?
C14 C15 1.379(6) . ?
C14 C19 1.392(6) . ?
C15 C16 1.385(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(7) . ?
C17 N2 1.476(6) . ?
C18 C19 1.382(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N2 O3 1.207(6) . ?
N2 O2 1.230(6) . ?

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
C2 C1 Cl2 113.0(3) . . ?
C2 C1 H1A 109.0 . . ?
Cl2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
Cl2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 C1 114.7(4) . . ?
N1 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 N1 102.7(5) . . ?
C4 C3 H3A 111.2 . . ?
N1 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
N1 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 Cl1 104.8(4) . . ?
C3 C4 H4A 110.8 . . ?
Cl1 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
Cl1 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C10 121.9(4) . . ?
N1 C5 C6 121.2(4) . . ?
C10 C5 C6 116.9(4) . . ?
C7 C6 C5 121.0(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.9(4) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 116.6(4) . . ?
C9 C8 C11 121.0(4) . . ?
C7 C8 C11 122.4(4) . . ?
C10 C9 C8 122.1(4) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C5 121.5(4) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
C12 C11 C8 128.0(4) . . ?
C12 C11 H11 116.0 . . ?
C8 C11 H11 116.0 . . ?
C11 C12 C13 122.7(4) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
O1 C13 C12 122.3(4) . . ?
O1 C13 C14 119.3(4) . . ?
C12 C13 C14 118.3(4) . . ?
C15 C14 C19 118.7(4) . . ?
C15 C14 C13 123.3(4) . . ?
C19 C14 C13 117.9(4) . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.3(5) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 122.4(4) . . ?
C16 C17 N2 119.4(5) . . ?
C18 C17 N2 118.2(5) . . ?
C17 C18 C19 118.5(4) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C18 C19 C14 120.7(5) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C5 N1 C2 121.1(3) . . ?
C5 N1 C3 119.8(4) . . ?
C2 N1 C3 118.2(4) . . ?
O3 N2 O2 123.2(5) . . ?
O3 N2 C17 119.6(5) . . ?
O2 N2 C17 117.2(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
Cl2 C1 C2 N1 86.7(4) . . . . ?
N1 C3 C4 Cl1 175.9(3) . . . . ?
N1 C5 C6 C7 178.9(4) . . . . ?
C10 C5 C6 C7 -0.6(6) . . . . ?
C5 C6 C7 C8 1.4(6) . . . . ?
C6 C7 C8 C9 -1.5(6) . . . . ?
C6 C7 C8 C11 178.0(4) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C11 C8 C9 C10 -178.6(4) . . . . ?
C8 C9 C10 C5 -0.2(7) . . . . ?
N1 C5 C10 C9 -179.5(4) . . . . ?
C6 C5 C10 C9 0.0(7) . . . . ?
C9 C8 C11 C12 171.9(4) . . . . ?
C7 C8 C11 C12 -7.6(7) . . . . ?
C8 C11 C12 C13 178.2(4) . . . . ?
C11 C12 C13 O1 8.8(7) . . . . ?
C11 C12 C13 C14 -168.3(4) . . . . ?
O1 C13 C14 C15 163.0(4) . . . . ?
C12 C13 C14 C15 -19.8(6) . . . . ?
O1 C13 C14 C19 -18.4(6) . . . . ?
C12 C13 C14 C19 158.8(4) . . . . ?
C19 C14 C15 C16 0.2(6) . . . . ?
C13 C14 C15 C16 178.9(4) . . . . ?
C14 C15 C16 C17 -0.8(6) . . . . ?
C15 C16 C17 C18 0.5(7) . . . . ?
C15 C16 C17 N2 -179.8(4) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
N2 C17 C18 C19 -179.4(4) . . . . ?
C17 C18 C19 C14 -0.9(6) . . . . ?
C15 C14 C19 C18 0.6(6) . . . . ?
C13 C14 C19 C18 -178.1(4) . . . . ?
C10 C5 N1 C2 -176.6(4) . . . . ?
C6 C5 N1 C2 3.9(7) . . . . ?
C10 C5 N1 C3 14.8(7) . . . . ?
C6 C5 N1 C3 -164.7(4) . . . . ?
C1 C2 N1 C5 73.7(6) . . . . ?
C1 C2 N1 C3 -117.5(5) . . . . ?
C4 C3 N1 C5 -93.0(5) . . . . ?
C4 C3 N1 C2 98.1(5) . . . . ?
C16 C17 N2 O3 178.1(5) . . . . ?
C18 C17 N2 O3 -2.2(7) . . . . ?
C16 C17 N2 O2 -2.1(7) . . . . ?
C18 C17 N2 O2 177.7(5) . . . . ?

_refine_diff_density_max         1.256
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
