# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

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

data_mo_chengp1_0m
_database_code_depnum_ccdc_archive 'CCDC 1041450'
_audit_update_record             
;
2014-12-29 deposited with the CCDC.
2015-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'ethyl 2-((4-chloro-2-((4-fluorophenyl)ethynyl)phenyl)amino)-2-oxoacetate'
_chemical_name_common            2q
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cl F N O3'
_chemical_formula_sum            'C18 H13 Cl F N O3'
_chemical_formula_weight         345.74

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'
F F 0.0171 0.0103 '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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   14.191(2)
_cell_length_b                   4.4973(7)
_cell_length_c                   25.988(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.570(2)
_cell_angle_gamma                90.00
_cell_volume                     1650.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2193
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.17

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8404
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15559
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_sigmaI/netI    0.0647
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         28.30
_reflns_number_total             4056
_reflns_number_gt                2803
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0428P)²+1.0682P] 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         4056
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.40500(4) 1.48640(15) 0.04996(2) 0.02233(16) Uani 1 1 d . . .
F1 F 0.02691(12) -0.1630(4) 0.33156(6) 0.0378(4) Uani 1 1 d . . .
O1 O 0.22751(10) 0.9804(4) 0.08485(6) 0.0247(4) Uani 1 1 d . . .
O2 O 0.13990(13) 0.7474(5) 0.13985(9) 0.0541(7) Uani 1 1 d . . .
O3 O 0.07495(13) 1.2663(6) 0.04480(10) 0.0699(9) Uani 1 1 d . . .
N1 N -0.01736(12) 1.0129(5) 0.09658(7) 0.0185(4) Uani 1 1 d . . .
H1 H -0.0132 0.8732 0.1204 0.022 Uiso 1 1 calc R . .
C1 C -0.01070(18) 0.0394(6) 0.29664(9) 0.0244(6) Uani 1 1 d . . .
C2 C -0.10181(18) 0.1345(6) 0.30004(9) 0.0235(5) Uani 1 1 d . . .
H2 H -0.1374 0.0629 0.3266 0.028 Uiso 1 1 calc R . .
C3 C -0.14067(17) 0.3381(5) 0.26375(9) 0.0188(5) Uani 1 1 d . . .
H3A H -0.2036 0.4073 0.2654 0.023 Uiso 1 1 calc R . .
C4 C -0.08751(16) 0.4413(5) 0.22488(8) 0.0160(5) Uani 1 1 d . . .
C5 C -0.12688(15) 0.6488(5) 0.18641(9) 0.0170(5) Uani 1 1 d . . .
C6 C -0.15724(15) 0.8183(5) 0.15363(8) 0.0153(5) Uani 1 1 d . . .
C7 C -0.18104(14) 1.0278(5) 0.11289(8) 0.0141(4) Uani 1 1 d . . .
C8 C -0.10837(15) 1.1285(5) 0.08349(8) 0.0140(5) Uani 1 1 d . . .
C9 C 0.06460(16) 1.0870(6) 0.07757(9) 0.0227(6) Uani 1 1 d . . .
C10 C 0.14798(16) 0.9127(6) 0.10457(10) 0.0224(6) Uani 1 1 d . . .
C11 C 0.31288(16) 0.8324(7) 0.10795(11) 0.0313(6) Uani 1 1 d . . .
H11A H 0.3050 0.6138 0.1061 0.038 Uiso 1 1 calc R . .
H11B H 0.3260 0.8905 0.1447 0.038 Uiso 1 1 calc R . .
C12 C 0.39235(16) 0.9278(7) 0.07789(10) 0.0301(7) Uani 1 1 d . . .
H12A H 0.3802 0.8590 0.0421 0.045 Uiso 1 1 calc R . .
H12B H 0.4518 0.8417 0.0935 0.045 Uiso 1 1 calc R . .
H12C H 0.3971 1.1452 0.0784 0.045 Uiso 1 1 calc R . .
C13 C -0.27267(15) 1.1387(5) 0.10174(9) 0.0160(5) Uani 1 1 d . . .
H13 H -0.3223 1.0730 0.1210 0.019 Uiso 1 1 calc R . .
C14 C -0.29094(15) 1.3440(5) 0.06257(8) 0.0165(5) Uani 1 1 d . . .
C15 C -0.21982(15) 1.4425(5) 0.03343(9) 0.0171(5) Uani 1 1 d . . .
H15 H -0.2337 1.5834 0.0065 0.021 Uiso 1 1 calc R . .
C16 C -0.12856(15) 1.3334(5) 0.04399(8) 0.0170(5) Uani 1 1 d . . .
H16 H -0.0797 1.3991 0.0241 0.020 Uiso 1 1 calc R . .
C17 C 0.00551(17) 0.3401(6) 0.22304(9) 0.0212(5) Uani 1 1 d . . .
H17 H 0.0423 0.4118 0.1970 0.025 Uiso 1 1 calc R . .
C18 C 0.04407(18) 0.1358(6) 0.25907(10) 0.0257(6) Uani 1 1 d . . .
H18 H 0.1068 0.0641 0.2579 0.031 Uiso 1 1 calc R . .


_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
Cl1 C14 1.742(2) . ?
F1 C1 1.357(3) . ?
O1 C10 1.320(3) . ?
O1 C11 1.459(3) . ?
O2 C10 1.194(3) . ?
O3 C9 1.192(3) . ?
N1 C9 1.349(3) . ?
N1 C8 1.403(3) . ?
N1 H1 0.8800 . ?
C1 C18 1.376(4) . ?
C1 C2 1.373(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(3) . ?
C3 H3A 0.9500 . ?
C4 C17 1.401(3) . ?
C4 C5 1.440(3) . ?
C5 C6 1.192(3) . ?
C6 C7 1.433(3) . ?
C7 C13 1.397(3) . ?
C7 C8 1.416(3) . ?
C8 C16 1.389(3) . ?
C9 C10 1.532(3) . ?
C11 C12 1.496(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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
C10 O1 C11 116.24(19) . . ?
C9 N1 C8 128.7(2) . . ?
C9 N1 H1 115.6 . . ?
C8 N1 H1 115.6 . . ?
F1 C1 C18 118.2(2) . . ?
F1 C1 C2 118.5(2) . . ?
C18 C1 C2 123.2(2) . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C17 119.5(2) . . ?
C3 C4 C5 121.1(2) . . ?
C17 C4 C5 119.3(2) . . ?
C6 C5 C4 177.9(2) . . ?
C5 C6 C7 172.5(2) . . ?
C13 C7 C8 119.1(2) . . ?
C13 C7 C6 122.41(19) . . ?
C8 C7 C6 118.50(19) . . ?
C16 C8 N1 122.97(19) . . ?
C16 C8 C7 120.2(2) . . ?
N1 C8 C7 116.9(2) . . ?
O3 C9 N1 126.8(2) . . ?
O3 C9 C10 122.0(2) . . ?
N1 C9 C10 111.2(2) . . ?
O2 C10 O1 126.2(2) . . ?
O2 C10 C9 122.9(2) . . ?
O1 C10 C9 110.8(2) . . ?
O1 C11 C12 107.0(2) . . ?
O1 C11 H11A 110.3 . . ?
C12 C11 H11A 110.3 . . ?
O1 C11 H11B 110.3 . . ?
C12 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C7 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C7 C13 H13 120.1 . . ?
C13 C14 C15 121.3(2) . . ?
C13 C14 Cl1 119.29(17) . . ?
C15 C14 Cl1 119.37(18) . . ?
C16 C15 C14 119.5(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C8 C16 C15 120.2(2) . . ?
C8 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C4 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C4 C17 H17 119.9 . . ?
C1 C18 C17 118.4(2) . . ?
C1 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?

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
F1 C1 C2 C3 -179.0(2) . . . . ?
C18 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C17 -0.6(3) . . . . ?
C2 C3 C4 C5 179.0(2) . . . . ?
C3 C4 C5 C6 -163(7) . . . . ?
C17 C4 C5 C6 17(7) . . . . ?
C4 C5 C6 C7 -33(9) . . . . ?
C5 C6 C7 C13 -172.4(18) . . . . ?
C5 C6 C7 C8 7(2) . . . . ?
C9 N1 C8 C16 5.0(4) . . . . ?
C9 N1 C8 C7 -174.6(2) . . . . ?
C13 C7 C8 C16 -0.4(3) . . . . ?
C6 C7 C8 C16 -179.4(2) . . . . ?
C13 C7 C8 N1 179.3(2) . . . . ?
C6 C7 C8 N1 0.2(3) . . . . ?
C8 N1 C9 O3 -1.1(5) . . . . ?
C8 N1 C9 C10 177.7(2) . . . . ?
C11 O1 C10 O2 1.5(4) . . . . ?
C11 O1 C10 C9 179.0(2) . . . . ?
O3 C9 C10 O2 174.7(3) . . . . ?
N1 C9 C10 O2 -4.1(4) . . . . ?
O3 C9 C10 O1 -2.9(4) . . . . ?
N1 C9 C10 O1 178.3(2) . . . . ?
C10 O1 C11 C12 176.8(2) . . . . ?
C8 C7 C13 C14 -0.2(3) . . . . ?
C6 C7 C13 C14 178.9(2) . . . . ?
C7 C13 C14 C15 0.5(4) . . . . ?
C7 C13 C14 Cl1 -178.66(17) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
Cl1 C14 C15 C16 178.87(18) . . . . ?
N1 C8 C16 C15 -179.1(2) . . . . ?
C7 C8 C16 C15 0.6(3) . . . . ?
C14 C15 C16 C8 -0.3(3) . . . . ?
C3 C4 C17 C18 0.9(4) . . . . ?
C5 C4 C17 C18 -178.7(2) . . . . ?
F1 C1 C18 C17 179.3(2) . . . . ?
C2 C1 C18 C17 0.3(4) . . . . ?
C4 C17 C18 C1 -0.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.065
