# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_NV0
_database_code_depnum_ccdc_archive 'CCDC 1586377'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-3,4-dichloro-2-(dimethylamino)-2-phenylbut-3-enenitrile
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cl2 N2'
_chemical_formula_weight         255.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.368(5)
_cell_length_b                   7.287(2)
_cell_length_c                   14.142(5)
_cell_angle_alpha                90.0
_cell_angle_beta                 113.436(8)
_cell_angle_gamma                90.0
_cell_volume                     1264.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9384
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      30.03
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9147
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9000
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.5
_reflns_number_total             2353
_reflns_number_gt                2193
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0623P)²+1.0009P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression 
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1343
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0

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
C11 C 0.30734(17) 0.7569(3) 0.27881(16) 0.0393(5) Uani 1 1 d . . .
C12 C 0.3020(2) 0.7124(3) 0.18157(19) 0.0526(6) Uani 1 1 d . . .
H12 H 0.2424 0.75 0.1234 0.063 Uiso 1 1 calc R . .
C13 C 0.3846(3) 0.6125(4) 0.1707(2) 0.0664(8) Uani 1 1 d . . .
H13 H 0.3803 0.5828 0.1052 0.08 Uiso 1 1 calc R . .
C14 C 0.4731(2) 0.5567(4) 0.2560(3) 0.0666(8) Uani 1 1 d . . .
H14 H 0.5288 0.49 0.2485 0.08 Uiso 1 1 calc R . .
C15 C 0.4789(2) 0.6001(4) 0.3529(2) 0.0616(7) Uani 1 1 d . . .
H15 H 0.5386 0.5619 0.4107 0.074 Uiso 1 1 calc R . .
C16 C 0.39683(19) 0.6998(3) 0.36486(19) 0.0495(6) Uani 1 1 d . . .
H16 H 0.4015 0.7286 0.4306 0.059 Uiso 1 1 calc R . .
C1 C 0.2449(2) 1.2070(4) 0.2318(2) 0.0586(7) Uani 1 1 d . . .
H1 H 0.2825 1.3166 0.2545 0.07 Uiso 1 1 calc R . .
Cl1 Cl 0.16041(9) 1.19345(13) 0.10359(6) 0.0910(4) Uani 1 1 d . . .
C2 C 0.26166(18) 1.0772(3) 0.30109(17) 0.0453(5) Uani 1 1 d . . .
Cl2 Cl 0.35861(6) 1.13163(10) 0.42285(5) 0.0716(3) Uani 1 1 d . . .
C3 C 0.21991(17) 0.8788(3) 0.29139(16) 0.0402(5) Uani 1 1 d . . .
C4 C 0.11546(19) 0.8581(3) 0.19793(18) 0.0498(6) Uani 1 1 d . . .
N4 N 0.03310(19) 0.8241(4) 0.13459(19) 0.0725(7) Uani 1 1 d . . .
N5 N 0.19884(15) 0.8272(3) 0.38208(14) 0.0461(5) Uani 1 1 d . . .
C5 C 0.1190(2) 0.9492(5) 0.3974(2) 0.0684(8) Uani 1 1 d . . .
H501 H 0.0488 0.9315 0.3425 0.103 Uiso 1 1 calc R . .
H502 H 0.1413 1.0745 0.3977 0.103 Uiso 1 1 calc R . .
H503 H 0.1148 0.9213 0.4621 0.103 Uiso 1 1 calc R . .
C6 C 0.1642(2) 0.6355(4) 0.3789(2) 0.0642(7) Uani 1 1 d . . .
H601 H 0.0965 0.6177 0.3207 0.096 Uiso 1 1 calc R . .
H602 H 0.1547 0.607 0.4411 0.096 Uiso 1 1 calc R . .
H603 H 0.2188 0.5563 0.3729 0.096 Uiso 1 1 calc R . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C11 0.0450(11) 0.0320(10) 0.0393(11) -0.0022(8) 0.0149(9) -0.0049(8)
C12 0.0675(15) 0.0471(13) 0.0433(12) -0.0041(10) 0.0222(11) -0.0019(11)
C13 0.094(2) 0.0538(15) 0.0686(18) -0.0135(13) 0.0511(17) -0.0035(14)
C14 0.0727(18) 0.0454(14) 0.097(2) -0.0058(14) 0.0502(17) 0.0053(13)
C15 0.0506(13) 0.0529(15) 0.0751(18) 0.0028(13) 0.0184(13) 0.0090(11)
C16 0.0506(13) 0.0476(13) 0.0448(12) -0.0015(10) 0.0131(10) 0.0031(10)
C1 0.0768(17) 0.0420(13) 0.0537(15) 0.0011(11) 0.0223(13) -0.0023(12)
Cl1 0.1290(8) 0.0739(6) 0.0503(4) 0.0179(4) 0.0149(4) -0.0132(5)
C2 0.0503(12) 0.0393(11) 0.0410(11) -0.0034(9) 0.0127(10) 0.0005(10)
Cl2 0.0859(5) 0.0542(4) 0.0503(4) -0.0050(3) 0.0012(3) -0.0202(3)
C3 0.0415(11) 0.0402(11) 0.0330(10) -0.0003(8) 0.0086(9) -0.0013(9)
C4 0.0477(13) 0.0505(13) 0.0432(12) 0.0024(10) 0.0094(11) -0.0011(10)
N4 0.0551(13) 0.0803(17) 0.0603(14) 0.0036(12) -0.0002(11) -0.0092(12)
N5 0.0481(10) 0.0499(11) 0.0414(10) 0.0015(8) 0.0191(8) 0.0003(8)
C5 0.0635(16) 0.086(2) 0.0627(16) 0.0010(15) 0.0323(14) 0.0152(15)
C6 0.0737(17) 0.0644(17) 0.0586(16) 0.0044(13) 0.0305(14) -0.0167(14)

_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
C11 C12 1.387(3) . ?
C11 C16 1.388(3) . ?
C11 C3 1.533(3) . ?
C12 C13 1.382(4) . ?
C13 C14 1.373(4) . ?
C14 C15 1.377(4) . ?
C15 C16 1.381(4) . ?
C1 C2 1.316(3) . ?
C1 Cl1 1.716(3) . ?
C2 C3 1.536(3) . ?
C2 Cl2 1.740(2) . ?
C3 N5 1.467(3) . ?
C3 C4 1.500(3) . ?
C4 N4 1.136(3) . ?
N5 C6 1.467(3) . ?
N5 C5 1.470(3) . ?


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
C12 C11 C16 119.0(2) . . ?
C12 C11 C3 120.6(2) . . ?
C16 C11 C3 120.19(19) . . ?
C13 C12 C11 120.4(3) . . ?
C14 C13 C12 120.4(3) . . ?
C13 C14 C15 119.6(2) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C11 120.0(2) . . ?
C2 C1 Cl1 126.2(2) . . ?
C1 C2 C3 131.5(2) . . ?
C1 C2 Cl2 114.33(19) . . ?
C3 C2 Cl2 113.84(16) . . ?
N5 C3 C4 108.01(18) . . ?
N5 C3 C11 111.92(17) . . ?
C4 C3 C11 108.95(18) . . ?
N5 C3 C2 110.63(18) . . ?
C4 C3 C2 110.55(18) . . ?
C11 C3 C2 106.78(17) . . ?
N4 C4 C3 170.7(3) . . ?
C6 N5 C3 112.66(19) . . ?
C6 N5 C5 110.0(2) . . ?
C3 N5 C5 112.15(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.06
####################################################################### 
# 
# 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_NV3b
_database_code_depnum_ccdc_archive 'CCDC 1586382'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-2-chloro-3-(2,3-dihydrobenzofuran-2-yl)-1-phenylprop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.1663(8)
_cell_length_b                   12.6929(11)
_cell_length_c                   17.4233(15)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     1363.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9887
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.56
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10108
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2540
_reflns_number_gt                2445
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0406P)²+0.3033P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0064(15)
_refine_ls_extinction_expression 
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_number_reflns         2540
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0

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 0.7544(4) 0.48724(15) 0.86245(11) 0.0495(5) Uani 1 1 d . . .
H1 H 0.6885 0.436 0.8926 0.059 Uiso 1 1 calc R . .
C2 C 0.9374(3) 0.45686(16) 0.82755(11) 0.0475(4) Uani 1 1 d . . .
Cl2 Cl 1.07858(9) 0.53938(4) 0.76680(3) 0.05974(17) Uani 1 1 d . . .
C3 C 1.0449(3) 0.35387(16) 0.84182(12) 0.0513(5) Uani 1 1 d . . .
O3 O 1.2357(3) 0.34228(14) 0.82714(12) 0.0793(5) Uani 1 1 d . . .
C11 C 0.9170(3) 0.26542(15) 0.87520(11) 0.0474(4) Uani 1 1 d . . .
C12 C 1.0160(4) 0.20109(17) 0.93016(12) 0.0602(6) Uani 1 1 d . . .
H12 H 1.1546 0.2168 0.9478 0.072 Uiso 1 1 calc R . .
C13 C 0.9074(5) 0.11456(18) 0.95796(14) 0.0737(7) Uani 1 1 d . . .
H13 H 0.9731 0.0722 0.9948 0.088 Uiso 1 1 calc R . .
C14 C 0.7042(5) 0.08999(17) 0.93219(15) 0.0689(6) Uani 1 1 d . . .
H14 H 0.6321 0.0316 0.9519 0.083 Uiso 1 1 calc R . .
C15 C 0.6060(4) 0.15146(18) 0.87719(15) 0.0630(6) Uani 1 1 d . . .
H15 H 0.4693 0.1337 0.8587 0.076 Uiso 1 1 calc R . .
C16 C 0.7111(4) 0.23922(17) 0.84971(12) 0.0539(5) Uani 1 1 d . . .
H16 H 0.643 0.2816 0.8135 0.065 Uiso 1 1 calc R . .
C21 C 0.6445(3) 0.58673(15) 0.86038(11) 0.0464(4) Uani 1 1 d . . .
O21 O 0.4577(2) 0.58869(10) 0.90493(8) 0.0493(3) Uani 1 1 d . . .
C22 C 0.6798(4) 0.68170(15) 0.82752(12) 0.0513(5) Uani 1 1 d . . .
H22 H 0.7945 0.6994 0.7953 0.062 Uiso 1 1 calc R . .
C23 C 0.5085(3) 0.74949(15) 0.85145(11) 0.0460(4) Uani 1 1 d . . .
C24 C 0.4517(4) 0.85478(16) 0.83797(12) 0.0588(5) Uani 1 1 d . . .
H24 H 0.5376 0.8978 0.8073 0.071 Uiso 1 1 calc R . .
C25 C 0.2655(4) 0.89271(17) 0.87134(14) 0.0626(6) Uani 1 1 d . . .
H25 H 0.2248 0.9623 0.8627 0.075 Uiso 1 1 calc R . .
C26 C 0.1359(4) 0.82886(18) 0.91802(14) 0.0644(6) Uani 1 1 d . . .
H26 H 0.0109 0.8569 0.9398 0.077 Uiso 1 1 calc R . .
C27 C 0.1893(4) 0.72528(17) 0.93241(14) 0.0589(5) Uani 1 1 d . . .
H27 H 0.1039 0.6825 0.9635 0.071 Uiso 1 1 calc R . .
C28 C 0.3756(3) 0.68875(14) 0.89838(11) 0.0449(4) Uani 1 1 d . . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0532(10) 0.0468(10) 0.0485(10) 0.0080(8) 0.0085(9) 0.0061(9)
C2 0.0474(10) 0.0498(10) 0.0453(9) 0.0002(8) 0.0041(8) 0.0017(10)
Cl2 0.0580(3) 0.0592(3) 0.0620(3) 0.0013(2) 0.0157(2) -0.0066(2)
C3 0.0482(11) 0.0547(11) 0.0510(11) -0.0034(9) 0.0048(9) 0.0088(9)
O3 0.0514(9) 0.0813(11) 0.1052(14) 0.0080(10) 0.0184(9) 0.0190(9)
C11 0.0521(10) 0.0441(10) 0.0462(10) -0.0031(8) 0.0023(9) 0.0162(9)
C12 0.0702(14) 0.0528(12) 0.0575(11) -0.0059(10) -0.0175(11) 0.0161(11)
C13 0.112(2) 0.0494(12) 0.0593(13) 0.0056(10) -0.0191(15) 0.0171(14)
C14 0.0954(19) 0.0425(11) 0.0688(14) 0.0013(11) 0.0023(14) 0.0028(12)
C15 0.0606(13) 0.0526(11) 0.0760(14) -0.0026(11) 0.0000(12) 0.0050(10)
C16 0.0547(12) 0.0512(11) 0.0559(11) 0.0054(9) -0.0001(9) 0.0143(10)
C21 0.0473(10) 0.0467(10) 0.0453(10) 0.0024(8) 0.0052(8) 0.0040(8)
O21 0.0528(8) 0.0417(7) 0.0535(7) 0.0059(6) 0.0126(6) 0.0077(6)
C22 0.0539(11) 0.0471(10) 0.0529(11) 0.0054(9) 0.0092(9) 0.0008(9)
C23 0.0537(11) 0.0409(9) 0.0434(9) -0.0021(8) -0.0033(8) 0.0040(8)
C24 0.0761(15) 0.0425(10) 0.0578(12) 0.0034(9) -0.0011(11) 0.0025(11)
C25 0.0772(15) 0.0449(11) 0.0659(13) -0.0025(10) -0.0054(13) 0.0157(11)
C26 0.0629(14) 0.0594(13) 0.0708(14) -0.0116(11) 0.0012(11) 0.0191(11)
C27 0.0581(12) 0.0536(11) 0.0650(13) -0.0009(10) 0.0086(11) 0.0061(10)
C28 0.0505(11) 0.0400(9) 0.0440(9) -0.0020(8) -0.0026(8) 0.0052(8)

_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 1.338(3) . ?
C1 C21 1.434(3) . ?
C2 C3 1.487(3) . ?
C2 Cl2 1.725(2) . ?
C3 O3 1.213(3) . ?
C3 C11 1.490(3) . ?
C11 C16 1.386(3) . ?
C11 C12 1.398(3) . ?
C12 C13 1.374(4) . ?
C13 C14 1.367(4) . ?
C14 C15 1.376(3) . ?
C15 C16 1.375(3) . ?
C21 C22 1.352(3) . ?
C21 O21 1.389(2) . ?
O21 C28 1.372(2) . ?
C22 C23 1.425(3) . ?
C23 C28 1.391(3) . ?
C23 C24 1.401(3) . ?
C24 C25 1.374(3) . ?
C25 C26 1.399(4) . ?
C26 C27 1.378(3) . ?
C27 C28 1.373(3) . ?


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 C21 129.85(19) . . ?
C1 C2 C3 123.62(18) . . ?
C1 C2 Cl2 121.96(16) . . ?
C3 C2 Cl2 114.27(14) . . ?
O3 C3 C2 120.3(2) . . ?
O3 C3 C11 120.28(19) . . ?
C2 C3 C11 119.44(17) . . ?
C16 C11 C12 118.6(2) . . ?
C16 C11 C3 122.73(18) . . ?
C12 C11 C3 118.45(19) . . ?
C13 C12 C11 119.7(2) . . ?
C14 C13 C12 120.9(2) . . ?
C13 C14 C15 120.2(2) . . ?
C16 C15 C14 119.6(2) . . ?
C15 C16 C11 121.0(2) . . ?
C22 C21 O21 110.74(17) . . ?
C22 C21 C1 136.04(18) . . ?
O21 C21 C1 113.18(16) . . ?
C28 O21 C21 106.03(14) . . ?
C21 C22 C23 107.16(18) . . ?
C28 C23 C24 118.67(19) . . ?
C28 C23 C22 105.91(17) . . ?
C24 C23 C22 135.4(2) . . ?
C25 C24 C23 118.2(2) . . ?
C24 C25 C26 121.4(2) . . ?
C27 C26 C25 121.5(2) . . ?
C28 C27 C26 116.3(2) . . ?
O21 C28 C27 125.83(18) . . ?
O21 C28 C23 110.15(17) . . ?
C27 C28 C23 124.02(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.037
#=============================================================================#=============================================================================
####################################################################### 
# 
# 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_NV3a
_database_code_depnum_ccdc_archive 'CCDC 1586381'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_NV3a                
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00417 Ang.
RESPONSE: This was a very thin platelet and hence a somewhat low-precision data set.
;
# Added during the CSD deposition process: Saturday 18 November 2017 06:30 PM
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-2-chloro-3-(2,3-dihydrobenzofuran-2-yl)-1-phenylprop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.087(4)
_cell_length_b                   6.124(4)
_cell_length_c                   13.998(7)
_cell_angle_alpha                90.0
_cell_angle_beta                 91.490(9)
_cell_angle_gamma                90.0
_cell_volume                     693.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5129
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      22.31
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.004
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8717
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5162
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         25.5
_reflns_number_total             2586
_reflns_number_gt                2295
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0318P)²+0.1295P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(7)
_refine_ls_number_reflns         2586
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.143
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0

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 0.5736(3) -0.0191(5) 0.76668(17) 0.0524(5) Uani 1 1 d . . .
H1 H 0.5239 -0.1556 0.761 0.063 Uiso 1 1 calc R . .
C2 C 0.5816(3) 0.0991(4) 0.68808(18) 0.0481(6) Uani 1 1 d . . .
Cl2 Cl 0.50690(8) -0.00138(11) 0.57966(4) 0.0666(2) Uani 1 1 d . . .
C3 C 0.6445(3) 0.3296(4) 0.67635(17) 0.0474(5) Uani 1 1 d . . .
O3 O 0.5473(2) 0.4776(3) 0.68303(14) 0.0686(5) Uani 1 1 d . . .
C11 C 0.8201(3) 0.3635(4) 0.65310(15) 0.0457(5) Uani 1 1 d . . .
C12 C 0.9383(3) 0.2028(4) 0.67028(17) 0.0548(6) Uani 1 1 d . . .
H12 H 0.9076 0.068 0.6948 0.066 Uiso 1 1 calc R . .
C13 C 1.1019(3) 0.2444(6) 0.65076(19) 0.0645(7) Uani 1 1 d . . .
H13 H 1.1818 0.1391 0.6646 0.077 Uiso 1 1 calc R . .
C14 C 1.1473(3) 0.4386(6) 0.61132(18) 0.0691(9) Uani 1 1 d . . .
H14 H 1.2575 0.4638 0.5974 0.083 Uiso 1 1 calc R . .
C15 C 1.0302(3) 0.5975(5) 0.59209(18) 0.0640(7) Uani 1 1 d . . .
H15 H 1.0612 0.7292 0.5648 0.077 Uiso 1 1 calc R . .
C16 C 0.8673(3) 0.5609(4) 0.61340(18) 0.0567(6) Uani 1 1 d . . .
H16 H 0.7886 0.6687 0.6012 0.068 Uiso 1 1 calc R . .
C21 C 0.6346(3) 0.0434(4) 0.86054(17) 0.0497(6) Uani 1 1 d . . .
O21 O 0.71418(19) 0.2435(3) 0.86878(10) 0.0492(4) Uani 1 1 d . . .
C22 C 0.6321(3) -0.0593(4) 0.94537(19) 0.0580(7) Uani 1 1 d . . .
H22 H 0.5859 -0.1954 0.9571 0.07 Uiso 1 1 calc R . .
C23 C 0.7133(3) 0.0783(4) 1.01421(17) 0.0521(6) Uani 1 1 d . . .
C24 C 0.7500(4) 0.0707(5) 1.11223(19) 0.0709(8) Uani 1 1 d . . .
H24 H 0.7191 -0.0483 1.1489 0.085 Uiso 1 1 calc R . .
C25 C 0.8332(4) 0.2446(6) 1.1528(2) 0.0772(9) Uani 1 1 d . . .
H25 H 0.8574 0.2424 1.2181 0.093 Uiso 1 1 calc R . .
C26 C 0.8820(4) 0.4215(5) 1.1002(2) 0.0719(8) Uani 1 1 d . . .
H26 H 0.9394 0.5345 1.1306 0.086 Uiso 1 1 calc R . .
C27 C 0.8477(3) 0.4352(4) 1.00324(17) 0.0571(7) Uani 1 1 d . . .
H27 H 0.8803 0.5543 0.967 0.069 Uiso 1 1 calc R . .
C28 C 0.7624(3) 0.2621(4) 0.96357(15) 0.0456(5) Uani 1 1 d . . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0491(12) 0.0438(12) 0.0645(14) -0.0050(13) 0.0036(10) -0.0055(12)
C2 0.0414(12) 0.0441(13) 0.0586(14) -0.0088(11) -0.0014(10) 0.0052(10)
Cl2 0.0731(4) 0.0634(4) 0.0627(4) -0.0172(4) -0.0130(3) 0.0063(3)
C3 0.0456(13) 0.0484(14) 0.0480(13) -0.0013(10) -0.0051(10) 0.0053(11)
O3 0.0510(9) 0.0502(10) 0.1044(14) -0.0022(11) 0.0013(9) 0.0116(10)
C11 0.0450(12) 0.0512(13) 0.0406(12) -0.0004(10) -0.0038(9) 0.0061(11)
C12 0.0525(14) 0.0610(16) 0.0509(13) 0.0020(12) -0.0001(11) 0.0120(13)
C13 0.0463(14) 0.082(2) 0.0655(16) 0.0015(16) 0.0012(12) 0.0131(14)
C14 0.0497(15) 0.102(3) 0.0560(15) -0.0055(16) 0.0055(12) -0.0105(16)
C15 0.0694(18) 0.0693(18) 0.0532(15) 0.0038(13) 0.0013(13) -0.0156(15)
C16 0.0607(15) 0.0524(16) 0.0566(14) 0.0024(11) -0.0060(11) -0.0012(12)
C21 0.0486(12) 0.0429(15) 0.0579(14) 0.0008(11) 0.0059(10) -0.0047(10)
O21 0.0542(9) 0.0461(9) 0.0471(9) 0.0025(7) 0.0002(7) -0.0067(8)
C22 0.0544(14) 0.0469(15) 0.0735(17) 0.0100(12) 0.0128(12) -0.0048(11)
C23 0.0489(13) 0.0555(15) 0.0520(13) 0.0091(11) 0.0058(10) 0.0052(12)
C24 0.0761(19) 0.081(2) 0.0563(16) 0.0200(15) 0.0090(13) 0.0074(16)
C25 0.085(2) 0.100(2) 0.0457(15) 0.0010(17) -0.0050(14) 0.007(2)
C26 0.0738(18) 0.084(2) 0.0578(16) -0.0107(15) -0.0074(13) -0.0012(16)
C27 0.0594(15) 0.0561(17) 0.0559(14) 0.0010(11) 0.0004(11) -0.0027(12)
C28 0.0452(12) 0.0486(13) 0.0431(12) 0.0027(11) 0.0045(9) 0.0043(11)

_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 1.320(3) . ?
C1 C21 1.443(3) . ?
C2 C3 1.511(4) . ?
C2 Cl2 1.732(3) . ?
C3 O3 1.205(3) . ?
C3 C11 1.480(3) . ?
C11 C16 1.388(3) . ?
C11 C12 1.389(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.366(4) . ?
C14 C15 1.380(4) . ?
C15 C16 1.376(4) . ?
C21 C22 1.344(3) . ?
C21 O21 1.387(3) . ?
O21 C28 1.378(3) . ?
C22 C23 1.427(4) . ?
C23 C28 1.393(3) . ?
C23 C24 1.397(4) . ?
C24 C25 1.375(5) . ?
C25 C26 1.373(5) . ?
C26 C27 1.381(4) . ?
C27 C28 1.374(3) . ?


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 C21 126.2(3) . . ?
C1 C2 C3 128.8(2) . . ?
C1 C2 Cl2 120.8(2) . . ?
C3 C2 Cl2 110.33(17) . . ?
O3 C3 C11 122.9(2) . . ?
O3 C3 C2 118.2(2) . . ?
C11 C3 C2 118.9(2) . . ?
C16 C11 C12 119.4(2) . . ?
C16 C11 C3 119.0(2) . . ?
C12 C11 C3 121.5(2) . . ?
C13 C12 C11 119.6(3) . . ?
C14 C13 C12 120.6(3) . . ?
C13 C14 C15 120.2(3) . . ?
C16 C15 C14 119.9(3) . . ?
C15 C16 C11 120.2(2) . . ?
C22 C21 O21 110.9(2) . . ?
C22 C21 C1 131.9(2) . . ?
O21 C21 C1 117.2(2) . . ?
C28 O21 C21 105.80(18) . . ?
C21 C22 C23 107.6(2) . . ?
C28 C23 C24 118.1(2) . . ?
C28 C23 C22 105.4(2) . . ?
C24 C23 C22 136.5(3) . . ?
C25 C24 C23 118.0(3) . . ?
C26 C25 C24 122.3(3) . . ?
C25 C26 C27 121.4(3) . . ?
C28 C27 C26 115.9(2) . . ?
C27 C28 O21 125.4(2) . . ?
C27 C28 C23 124.4(2) . . ?
O21 C28 C23 110.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_NV2b
_database_code_depnum_ccdc_archive 'CCDC 1586380'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-2-chloro-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl O2'
_chemical_formula_weight         272.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.858(3)
_cell_length_b                   11.306(5)
_cell_length_c                   27.121(11)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2716.0(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.02
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1136
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9151
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18717
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0088
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         25.5
_reflns_number_total             2525
_reflns_number_gt                2299
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0685P)²+0.7942P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.123
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.0
_refine_ls_shift/su_mean         0.0

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 0.39464(19) 0.92175(13) 0.44012(6) 0.0454(4) Uani 1 1 d . . .
H1 H 0.4762 0.888 0.4237 0.054 Uiso 1 1 calc R . .
C2 C 0.31559(18) 0.99642(14) 0.41167(6) 0.0477(4) Uani 1 1 d . . .
Cl2 Cl 0.16366(6) 1.07830(5) 0.43347(2) 0.0680(2) Uani 1 1 d . . .
C3 C 0.3558(2) 1.02433(15) 0.35986(7) 0.0522(4) Uani 1 1 d . . .
O3 O 0.3061(2) 1.11292(13) 0.34005(6) 0.0794(5) Uani 1 1 d . . .
C11 C 0.45748(19) 0.94424(15) 0.33117(6) 0.0481(4) Uani 1 1 d . . .
C12 C 0.4406(2) 0.82157(15) 0.33161(6) 0.0527(4) Uani 1 1 d . . .
H12 H 0.3716 0.7863 0.3529 0.063 Uiso 1 1 calc R . .
C13 C 0.5267(2) 0.75269(18) 0.30038(7) 0.0651(5) Uani 1 1 d . . .
H13 H 0.5143 0.671 0.3004 0.078 Uiso 1 1 calc R . .
C14 C 0.6309(3) 0.8039(2) 0.26924(7) 0.0750(6) Uani 1 1 d . . .
H14 H 0.6892 0.7568 0.2485 0.09 Uiso 1 1 calc R . .
C15 C 0.6484(3) 0.9248(2) 0.26890(7) 0.0752(6) Uani 1 1 d . . .
H15 H 0.7191 0.9593 0.248 0.09 Uiso 1 1 calc R . .
C16 C 0.5620(2) 0.99544(19) 0.29931(6) 0.0621(5) Uani 1 1 d . . .
H16 H 0.5735 1.0772 0.2985 0.075 Uiso 1 1 calc R . .
C21 C 0.38126(17) 0.88180(13) 0.49081(6) 0.0433(4) Uani 1 1 d . . .
C22 C 0.4838(2) 0.79551(15) 0.50613(6) 0.0503(4) Uani 1 1 d . . .
H22 H 0.5572 0.7703 0.4839 0.06 Uiso 1 1 calc R . .
C23 C 0.4817(2) 0.74593(16) 0.55248(6) 0.0543(4) Uani 1 1 d . . .
H23 H 0.5517 0.6882 0.5611 0.065 Uiso 1 1 calc R . .
C24 C 0.3742(2) 0.78310(17) 0.58611(6) 0.0530(4) Uani 1 1 d . . .
C25 C 0.2731(2) 0.87098(18) 0.57262(7) 0.0596(5) Uani 1 1 d . . .
H25 H 0.2023 0.8973 0.5954 0.071 Uiso 1 1 calc R . .
C26 C 0.2755(2) 0.92002(16) 0.52612(6) 0.0540(4) Uani 1 1 d . . .
H26 H 0.2065 0.9789 0.518 0.065 Uiso 1 1 calc R . .
O27 O 0.36020(16) 0.74058(14) 0.63276(5) 0.0726(4) Uani 1 1 d . . .
C27 C 0.4599(3) 0.6486(2) 0.64792(8) 0.0787(6) Uani 1 1 d . . .
H271 H 0.4482 0.5817 0.6265 0.118 Uiso 1 1 calc R . .
H272 H 0.4364 0.6257 0.6811 0.118 Uiso 1 1 calc R . .
H273 H 0.5622 0.6764 0.6464 0.118 Uiso 1 1 calc R . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0434(8) 0.0429(8) 0.0499(8) -0.0078(6) 0.0027(7) 0.0009(6)
C2 0.0458(8) 0.0415(8) 0.0559(9) -0.0050(7) 0.0014(7) 0.0022(6)
Cl2 0.0627(3) 0.0647(3) 0.0767(4) -0.0001(2) 0.0076(2) 0.0226(2)
C3 0.0546(9) 0.0456(9) 0.0564(9) 0.0040(7) -0.0040(7) 0.0013(7)
O3 0.0953(11) 0.0653(9) 0.0777(9) 0.0199(7) 0.0060(8) 0.0255(8)
C11 0.0505(9) 0.0526(9) 0.0411(8) 0.0029(7) -0.0059(7) -0.0003(7)
C12 0.0578(10) 0.0526(9) 0.0477(9) 0.0000(7) -0.0041(7) -0.0015(8)
C13 0.0778(12) 0.0634(11) 0.0541(10) -0.0107(8) -0.0075(10) 0.0086(10)
C14 0.0752(13) 0.1019(17) 0.0477(10) -0.0138(11) 0.0024(9) 0.0161(12)
C15 0.0689(13) 0.1079(19) 0.0487(10) 0.0047(11) 0.0099(9) -0.0065(12)
C16 0.0691(12) 0.0678(11) 0.0494(9) 0.0072(8) 0.0007(9) -0.0092(9)
C21 0.0425(8) 0.0417(8) 0.0457(8) -0.0088(6) -0.0002(6) -0.0024(6)
C22 0.0532(9) 0.0499(8) 0.0477(9) -0.0065(7) 0.0068(7) 0.0060(7)
C23 0.0599(10) 0.0548(9) 0.0483(9) -0.0031(7) 0.0003(8) 0.0067(8)
C24 0.0518(9) 0.0624(10) 0.0449(8) -0.0054(8) 0.0006(7) -0.0088(8)
C25 0.0499(10) 0.0774(13) 0.0514(9) -0.0105(8) 0.0094(8) 0.0025(9)
C26 0.0463(9) 0.0600(10) 0.0556(9) -0.0086(8) 0.0024(7) 0.0060(7)
O27 0.0735(9) 0.0965(11) 0.0478(7) 0.0060(7) 0.0091(6) 0.0031(8)
C27 0.0900(16) 0.0883(15) 0.0579(12) 0.0165(11) 0.0003(11) -0.0010(12)

_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 1.341(2) . ?
C1 C21 1.452(2) . ?
C2 C3 1.483(3) . ?
C2 Cl2 1.7372(17) . ?
C3 O3 1.219(2) . ?
C3 C11 1.496(2) . ?
C11 C16 1.392(2) . ?
C11 C12 1.395(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.378(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.380(3) . ?
C21 C22 1.396(2) . ?
C21 C26 1.408(2) . ?
C22 C23 1.376(2) . ?
C23 C24 1.384(3) . ?
C24 O27 1.359(2) . ?
C24 C25 1.387(3) . ?
C25 C26 1.378(3) . ?
O27 C27 1.425(3) . ?


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 C21 134.27(15) . . ?
C1 C2 C3 123.61(15) . . ?
C1 C2 Cl2 122.97(13) . . ?
C3 C2 Cl2 113.26(12) . . ?
O3 C3 C2 120.38(17) . . ?
O3 C3 C11 119.05(16) . . ?
C2 C3 C11 120.57(14) . . ?
C16 C11 C12 119.32(17) . . ?
C16 C11 C3 118.14(16) . . ?
C12 C11 C3 122.22(15) . . ?
C13 C12 C11 119.78(18) . . ?
C14 C13 C12 120.6(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C15 C16 C11 120.0(2) . . ?
C22 C21 C26 116.44(15) . . ?
C22 C21 C1 116.48(14) . . ?
C26 C21 C1 127.08(15) . . ?
C23 C22 C21 123.18(15) . . ?
C22 C23 C24 119.19(17) . . ?
O27 C24 C23 124.69(18) . . ?
O27 C24 C25 116.09(16) . . ?
C23 C24 C25 119.21(16) . . ?
C26 C25 C24 121.32(16) . . ?
C25 C26 C21 120.61(17) . . ?
C24 O27 C27 118.04(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_NV1b
_database_code_depnum_ccdc_archive 'CCDC 1586378'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(Z)-2-chloro-3-(4-methylphenyl)-1-phenylprop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl O'
_chemical_formula_weight         256.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.8054(8)
_cell_length_b                   11.6093(11)
_cell_length_c                   26.7629(15)
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
_cell_angle_gamma                90.0
_cell_volume                     2735.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9816
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.22
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9344
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18840
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_sigmaI/netI    0.0088
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2543
_reflns_number_gt                2317
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0599P)²+0.6839P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0202(16)
_refine_ls_extinction_expression 
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_number_reflns         2543
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001

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 0.39517(16) 0.57592(11) 0.44156(5) 0.0443(3) Uani 1 1 d . . .
H1 H 0.4782 0.6056 0.4244 0.053 Uiso 1 1 calc R . .
C2 C 0.31254(16) 0.50338(12) 0.41382(5) 0.0483(3) Uani 1 1 d . . .
Cl2 Cl 0.15762(5) 0.42777(4) 0.43621(2) 0.0774(2) Uani 1 1 d . . .
C3 C 0.35310(17) 0.47362(13) 0.36142(6) 0.0537(4) Uani 1 1 d . . .
O3 O 0.31145(18) 0.38329(11) 0.34318(5) 0.0829(4) Uani 1 1 d . . .
C11 C 0.44300(17) 0.55611(13) 0.33059(5) 0.0504(4) Uani 1 1 d . . .
C12 C 0.41701(19) 0.67414(14) 0.33150(6) 0.0558(4) Uani 1 1 d . . .
H12 H 0.3504 0.7054 0.3548 0.067 Uiso 1 1 calc R . .
C13 C 0.4900(2) 0.74502(17) 0.29778(6) 0.0690(5) Uani 1 1 d . . .
H13 H 0.4706 0.8238 0.298 0.083 Uiso 1 1 calc R . .
C14 C 0.5916(2) 0.7000(2) 0.26371(6) 0.0781(6) Uani 1 1 d . . .
H14 H 0.641 0.7483 0.2413 0.094 Uiso 1 1 calc R . .
C15 C 0.6196(3) 0.5835(2) 0.26303(7) 0.0814(6) Uani 1 1 d . . .
H15 H 0.6891 0.5532 0.2404 0.098 Uiso 1 1 calc R . .
C16 C 0.5448(2) 0.51140(16) 0.29586(6) 0.0676(5) Uani 1 1 d . . .
H16 H 0.5626 0.4325 0.2948 0.081 Uiso 1 1 calc R . .
C21 C 0.38489(15) 0.61904(12) 0.49249(5) 0.0450(3) Uani 1 1 d . . .
C22 C 0.49035(19) 0.70280(13) 0.50574(6) 0.0563(4) Uani 1 1 d . . .
H22 H 0.5655 0.7231 0.483 0.068 Uiso 1 1 calc R . .
C23 C 0.4867(2) 0.75665(15) 0.55158(6) 0.0672(5) Uani 1 1 d . . .
H23 H 0.5588 0.8126 0.559 0.081 Uiso 1 1 calc R . .
C24 C 0.3779(2) 0.72896(16) 0.58658(6) 0.0653(5) Uani 1 1 d . . .
C25 C 0.2767(2) 0.64268(18) 0.57466(6) 0.0685(5) Uani 1 1 d . . .
H25 H 0.2049 0.6207 0.5983 0.082 Uiso 1 1 calc R . .
C26 C 0.27795(18) 0.58753(15) 0.52876(6) 0.0586(4) Uani 1 1 d . . .
H26 H 0.2079 0.5296 0.522 0.07 Uiso 1 1 calc R . .
C27 C 0.3707(3) 0.7935(2) 0.63575(8) 0.1003(8) Uani 1 1 d . . .
H271 H 0.3342 0.8703 0.63 0.15 Uiso 1 1 calc R . .
H272 H 0.4703 0.7968 0.6503 0.15 Uiso 1 1 calc R . .
H273 H 0.303 0.7543 0.6581 0.15 Uiso 1 1 calc R . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0438(7) 0.0456(7) 0.0434(7) 0.0064(5) 0.0027(5) 0.0003(5)
C2 0.0476(7) 0.0457(7) 0.0516(8) 0.0040(6) 0.0028(6) -0.0028(6)
Cl2 0.0695(3) 0.0772(3) 0.0855(4) -0.0082(2) 0.0171(2) -0.0296(2)
C3 0.0564(8) 0.0522(8) 0.0526(8) -0.0069(7) -0.0046(6) -0.0025(7)
O3 0.1037(10) 0.0698(8) 0.0751(8) -0.0232(6) 0.0078(7) -0.0278(7)
C11 0.0547(8) 0.0589(8) 0.0374(7) -0.0044(6) -0.0049(6) -0.0001(7)
C12 0.0620(9) 0.0618(9) 0.0437(7) 0.0039(6) -0.0010(6) 0.0081(7)
C13 0.0804(11) 0.0702(10) 0.0565(9) 0.0173(8) -0.0012(8) 0.0023(9)
C14 0.0823(12) 0.1028(15) 0.0490(9) 0.0171(9) 0.0053(9) -0.0086(11)
C15 0.0847(13) 0.1076(17) 0.0518(10) -0.0081(9) 0.0178(9) 0.0012(11)
C16 0.0778(11) 0.0712(10) 0.0537(9) -0.0141(8) 0.0066(8) 0.0035(9)
C21 0.0467(7) 0.0473(7) 0.0410(7) 0.0076(5) 0.0003(5) 0.0059(6)
C22 0.0659(9) 0.0572(8) 0.0460(8) 0.0023(6) 0.0035(7) -0.0070(7)
C23 0.0849(12) 0.0638(10) 0.0530(9) -0.0074(7) -0.0033(8) -0.0051(9)
C24 0.0756(11) 0.0755(11) 0.0449(8) -0.0044(7) -0.0025(7) 0.0233(9)
C25 0.0594(10) 0.0985(13) 0.0478(8) 0.0071(8) 0.0127(7) 0.0141(10)
C26 0.0498(8) 0.0756(10) 0.0504(8) 0.0062(7) 0.0054(7) 0.0005(7)
C27 0.126(2) 0.1180(19) 0.0569(11) -0.0230(12) 0.0034(12) 0.0298(15)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.338(2) . ?
C1 C21 1.455(2) . ?
C2 C3 1.488(2) . ?
C2 Cl2 1.7293(14) . ?
C3 O3 1.2134(19) . ?
C3 C11 1.492(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.392(2) . ?
C12 C13 1.380(2) . ?
C13 C14 1.381(3) . ?
C14 C15 1.375(3) . ?
C15 C16 1.380(3) . ?
C21 C22 1.391(2) . ?
C21 C26 1.401(2) . ?
C22 C23 1.377(2) . ?
C23 C24 1.378(3) . ?
C24 C25 1.378(3) . ?
C24 C27 1.516(2) . ?
C25 C26 1.385(2) . ?


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 C21 134.64(13) . . ?
C1 C2 C3 122.59(13) . . ?
C1 C2 Cl2 123.79(11) . . ?
C3 C2 Cl2 113.47(11) . . ?
O3 C3 C2 120.48(15) . . ?
O3 C3 C11 119.53(14) . . ?
C2 C3 C11 119.98(12) . . ?
C12 C11 C16 119.05(15) . . ?
C12 C11 C3 122.42(14) . . ?
C16 C11 C3 118.15(15) . . ?
C13 C12 C11 119.99(15) . . ?
C12 C13 C14 120.53(18) . . ?
C15 C14 C13 119.84(18) . . ?
C14 C15 C16 120.15(18) . . ?
C15 C16 C11 120.42(18) . . ?
C22 C21 C26 117.06(14) . . ?
C22 C21 C1 115.96(12) . . ?
C26 C21 C1 126.95(14) . . ?
C23 C22 C21 121.93(15) . . ?
C22 C23 C24 121.04(17) . . ?
C25 C24 C23 117.51(15) . . ?
C25 C24 C27 122.23(19) . . ?
C23 C24 C27 120.3(2) . . ?
C24 C25 C26 122.41(16) . . ?
C25 C26 C21 119.93(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_NV2a
_database_code_depnum_ccdc_archive 'CCDC 1586379'
_audit_update_record             
;
2017-11-18 deposited with the CCDC.
2018-01-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_NV2a                
;
PROBLEM: Hirshfeld Test Diff for  C14      --C15       ..        8.0 s.u.
RESPONSE: Thermal ellipsoids in the OMe group and also in the phenyl group suggest a minor problem with crystal quality. We could not construct a disorder model fitting the disagreeable thermal motions.
;
_vrf_PLAT148_NV2a                
;
PROBLEM: s.u. on the      a    - Axis is (Too) Large ....      0.020 Ang.
RESPONSE: This probably indicates problems with crystal quality 
;
_vrf_PLAT230_NV2a_2              
;
PROBLEM: Hirshfeld Test Diff for  O27      --C27       ..        5.8 s.u.
RESPONSE: Thermal ellipsoids in the OMe group and also in the phenyl group suggest a minor problem with crystal quality. We could not construct a disorder model fitting the disagreeable thermal motions.
;
# Added during the CSD deposition process: Saturday 18 November 2017 06:30 PM
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(E)-2-chloro-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl O2'
_chemical_formula_weight         272.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0 0.0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   14.28(2)
_cell_length_b                   9.823(14)
_cell_length_c                   9.912(14)
_cell_angle_alpha                90.0
_cell_angle_beta                 98.27(2)
_cell_angle_gamma                90.0
_cell_volume                     1376(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8683
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.19
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9151
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_process_details   SADABS
_exptl_special_details           ' ? '
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker D8 three-circle diffractometer with an APEX-II CCD detector
;
_diffrn_measurement_method       'area detector φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9855
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         25.5
_reflns_number_total             2549
_reflns_number_gt                2197
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'APEX2 software suite'
_computing_cell_refinement       'APEX2 software suite'
_computing_data_reduction        'APEX2 software suite'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(7)
_refine_ls_extinction_expression 
;
Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
;
_refine_ls_number_reflns         2549
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1886
_refine_ls_goodness_of_fit_ref   1.685
_refine_ls_restrained_S_all      1.685
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0

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 0.76175(13) 0.84548(19) 0.27499(19) 0.0646(5) Uani 1 1 d . . .
H1 H 0.7563 0.7942 0.1954 0.078 Uiso 1 1 calc R . .
C2 C 0.71126(13) 0.9595(2) 0.27127(19) 0.0661(5) Uani 1 1 d . . .
Cl2 Cl 0.65034(5) 1.01525(7) 0.11730(6) 0.0972(4) Uani 1 1 d . . .
C3 C 0.70290(14) 1.0556(2) 0.3858(2) 0.0687(5) Uani 1 1 d . . .
O3 O 0.72850(15) 1.17158(15) 0.3806(2) 0.1025(6) Uani 1 1 d . . .
C11 C 0.65948(12) 1.00542(17) 0.50478(19) 0.0592(5) Uani 1 1 d . . .
C12 C 0.60997(13) 0.88489(19) 0.5005(2) 0.0676(5) Uani 1 1 d . . .
H12 H 0.6062 0.8293 0.424 0.081 Uiso 1 1 calc R . .
C13 C 0.56578(16) 0.8462(3) 0.6102(3) 0.0856(7) Uani 1 1 d . . .
H13 H 0.5315 0.7655 0.607 0.103 Uiso 1 1 calc R . .
C14 C 0.57308(17) 0.9293(3) 0.7250(2) 0.0951(8) Uani 1 1 d . . .
H14 H 0.5441 0.9034 0.7993 0.114 Uiso 1 1 calc R . .
C15 C 0.62204(18) 1.0474(3) 0.7293(2) 0.0901(7) Uani 1 1 d . . .
H15 H 0.6268 1.1018 0.8068 0.108 Uiso 1 1 calc R . .
C16 C 0.66499(14) 1.0880(2) 0.6202(2) 0.0741(6) Uani 1 1 d . . .
H16 H 0.6976 1.1701 0.6235 0.089 Uiso 1 1 calc R . .
C21 C 0.82474(12) 0.79352(17) 0.39206(17) 0.0578(5) Uani 1 1 d . . .
C22 C 0.87957(12) 0.87865(17) 0.4834(2) 0.0618(5) Uani 1 1 d . . .
H22 H 0.8736 0.9724 0.4721 0.074 Uiso 1 1 calc R . .
C23 C 0.94213(12) 0.82888(18) 0.5895(2) 0.0619(5) Uani 1 1 d . . .
H23 H 0.9777 0.8883 0.6494 0.074 Uiso 1 1 calc R . .
C24 C 0.95217(12) 0.68898(18) 0.60699(19) 0.0619(5) Uani 1 1 d . . .
C25 C 0.89832(14) 0.60239(19) 0.5172(2) 0.0680(5) Uani 1 1 d . . .
H25 H 0.904 0.5087 0.5294 0.082 Uiso 1 1 calc R . .
C26 C 0.83668(13) 0.65310(18) 0.4107(2) 0.0654(5) Uani 1 1 d . . .
H26 H 0.8022 0.5934 0.3498 0.079 Uiso 1 1 calc R . .
O27 O 1.01308(10) 0.62836(14) 0.70671(15) 0.0792(5) Uani 1 1 d . . .
C27 C 1.07615(16) 0.7134(3) 0.7926(3) 0.0904(7) Uani 1 1 d . . .
H271 H 1.114 0.7648 0.7382 0.136 Uiso 1 1 calc R . .
H272 H 1.1165 0.6583 0.8565 0.136 Uiso 1 1 calc R . .
H273 H 1.0406 0.7746 0.8411 0.136 Uiso 1 1 calc R . .


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0634(10) 0.0796(12) 0.0525(10) -0.0043(8) 0.0137(8) -0.0003(8)
C2 0.0649(10) 0.0813(12) 0.0530(10) 0.0072(8) 0.0118(8) -0.0003(9)
Cl2 0.1048(6) 0.1223(6) 0.0617(5) 0.0154(3) 0.0027(3) 0.0240(3)
C3 0.0707(11) 0.0694(11) 0.0661(12) 0.0080(9) 0.0098(9) 0.0066(9)
O3 0.1443(16) 0.0700(10) 0.0995(14) 0.0031(9) 0.0390(11) -0.0130(10)
C11 0.0559(9) 0.0668(10) 0.0538(10) 0.0016(7) 0.0042(7) 0.0118(7)
C12 0.0671(10) 0.0731(11) 0.0635(11) 0.0042(8) 0.0125(8) 0.0083(8)
C13 0.0738(12) 0.0934(14) 0.0932(17) 0.0254(12) 0.0247(11) 0.0135(11)
C14 0.0868(15) 0.140(2) 0.0630(13) 0.0237(14) 0.0250(11) 0.0371(16)
C15 0.0936(15) 0.1212(19) 0.0551(12) -0.0046(12) 0.0097(10) 0.0293(15)
C16 0.0701(11) 0.0850(13) 0.0642(12) -0.0093(9) -0.0001(9) 0.0145(10)
C21 0.0543(9) 0.0675(10) 0.0538(10) -0.0039(7) 0.0149(7) 0.0001(7)
C22 0.0656(10) 0.0562(9) 0.0643(11) -0.0002(8) 0.0113(8) -0.0005(7)
C23 0.0617(9) 0.0641(10) 0.0600(10) -0.0042(8) 0.0092(8) -0.0030(7)
C24 0.0607(9) 0.0681(10) 0.0600(10) 0.0047(8) 0.0197(8) 0.0085(7)
C25 0.0738(11) 0.0566(9) 0.0765(13) -0.0017(8) 0.0213(10) 0.0057(8)
C26 0.0660(10) 0.0644(10) 0.0684(11) -0.0145(8) 0.0181(9) -0.0038(8)
O27 0.0804(9) 0.0836(10) 0.0726(10) 0.0096(7) 0.0077(7) 0.0151(7)
C27 0.0733(12) 0.1167(18) 0.0785(15) 0.0259(13) 0.0023(11) 0.0042(12)

_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 1.330(3) . ?
C1 C21 1.455(3) . ?
C2 C3 1.494(3) . ?
C2 Cl2 1.733(3) . ?
C3 O3 1.200(3) . ?
C3 C11 1.493(3) . ?
C11 C12 1.377(3) . ?
C11 C16 1.395(3) . ?
C12 C13 1.386(3) . ?
C13 C14 1.392(4) . ?
C14 C15 1.352(5) . ?
C15 C16 1.377(4) . ?
C21 C22 1.389(3) . ?
C21 C26 1.399(3) . ?
C22 C23 1.368(3) . ?
C23 C24 1.390(3) . ?
C24 O27 1.357(3) . ?
C24 C25 1.382(3) . ?
C25 C26 1.368(3) . ?
O27 C27 1.418(3) . ?


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 C21 126.04(18) . . ?
C1 C2 C3 127.84(19) . . ?
C1 C2 Cl2 119.48(16) . . ?
C3 C2 Cl2 112.60(17) . . ?
O3 C3 C11 120.75(19) . . ?
O3 C3 C2 120.61(19) . . ?
C11 C3 C2 118.62(19) . . ?
C12 C11 C16 119.53(19) . . ?
C12 C11 C3 121.98(17) . . ?
C16 C11 C3 118.4(2) . . ?
C11 C12 C13 120.1(2) . . ?
C12 C13 C14 119.5(3) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 120.7(2) . . ?
C15 C16 C11 119.8(2) . . ?
C22 C21 C26 117.45(18) . . ?
C22 C21 C1 122.34(18) . . ?
C26 C21 C1 120.07(17) . . ?
C23 C22 C21 122.04(18) . . ?
C22 C23 C24 119.56(17) . . ?
O27 C24 C25 115.97(19) . . ?
O27 C24 C23 124.66(18) . . ?
C25 C24 C23 119.36(19) . . ?
C26 C25 C24 120.64(19) . . ?
C25 C26 C21 120.92(17) . . ?
C24 O27 C27 117.63(19) . . ?

_diffrn_measured_fraction_theta_max 1.0
_diffrn_reflns_theta_full        25.5
_diffrn_measured_fraction_theta_full 1.0
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
