# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_ag-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 Cl N O'
_chemical_formula_sum            'C21 H14 Cl N O'
_chemical_formula_weight         331.78

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.6383(7)
_cell_length_b                   9.0793(8)
_cell_length_c                   12.1907(10)
_cell_angle_alpha                103.312(3)
_cell_angle_beta                 93.496(3)
_cell_angle_gamma                96.408(3)
_cell_volume                     814.28(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10162
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         28.38
_reflns_number_total             4062
_reflns_number_gt                2881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0619P)²+0.0863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3835
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Cl1 Cl 0.35946(7) 0.67432(7) 0.57303(3) 0.07756(19) Uani 1 1 d . . .
C7 C 0.79478(17) 0.76594(14) 1.08507(11) 0.0386(3) Uani 1 1 d . . .
C6 C 0.51225(18) 0.78233(15) 1.14693(11) 0.0408(3) Uani 1 1 d . . .
C8 C 0.80799(18) 0.79391(15) 1.20905(11) 0.0409(3) Uani 1 1 d . . .
C5 C 0.64073(19) 0.80276(15) 1.24610(11) 0.0421(3) Uani 1 1 d . . .
C4 C 0.6124(2) 0.82449(19) 1.35957(13) 0.0551(4) Uani 1 1 d . . .
H4 H 0.4998 0.8316 1.3837 0.066 Uiso 1 1 calc R . .
C1 C 0.9539(2) 0.80461(18) 1.28583(13) 0.0512(4) Uani 1 1 d . . .
H1 H 1.0668 0.7980 1.2620 0.061 Uiso 1 1 calc R . .
C3 C 0.7575(3) 0.8351(2) 1.43541(13) 0.0645(5) Uani 1 1 d . . .
H3 H 0.7427 0.8490 1.5121 0.077 Uiso 1 1 calc R . .
C2 C 0.9249(2) 0.8254(2) 1.39875(13) 0.0624(4) Uani 1 1 d . . .
H2 H 1.0205 0.8332 1.4517 0.075 Uiso 1 1 calc R . .
O1 O 0.35287(13) 0.78350(12) 1.14320(9) 0.0520(3) Uani 1 1 d . . .
C16 C 0.53494(17) 0.74725(15) 0.94083(11) 0.0382(3) Uani 1 1 d . . .
C21 C 0.58819(18) 0.85704(15) 0.88376(12) 0.0427(3) Uani 1 1 d . . .
H21 H 0.6619 0.9450 0.9214 0.051 Uiso 1 1 calc R . .
C19 C 0.41931(19) 0.70605(18) 0.71693(12) 0.0478(3) Uani 1 1 d . . .
C17 C 0.41433(18) 0.62133(16) 0.88771(12) 0.0454(3) Uani 1 1 d . . .
H17 H 0.3730 0.5510 0.9279 0.054 Uiso 1 1 calc R . .
C9 C 0.92866(18) 0.74766(16) 1.02004(12) 0.0443(3) Uani 1 1 d . . .
H9 H 1.0404 0.7617 1.0585 0.053 Uiso 1 1 calc R . .
C20 C 0.5320(2) 0.83621(17) 0.77073(12) 0.0469(3) Uani 1 1 d . . .
H20 H 0.5694 0.9086 0.7313 0.056 Uiso 1 1 calc R . .
C10 C 0.92395(17) 0.70825(16) 0.89539(12) 0.0424(3) Uani 1 1 d . . .
C15 C 0.8383(2) 0.57020(17) 0.83119(13) 0.0496(3) Uani 1 1 d . . .
H15 H 0.7858 0.4988 0.8670 0.060 Uiso 1 1 calc R . .
C18 C 0.3556(2) 0.60048(17) 0.77479(13) 0.0505(4) Uani 1 1 d . . .
H18 H 0.2745 0.5166 0.7385 0.061 Uiso 1 1 calc R . .
C11 C 1.0077(2) 0.81052(18) 0.83930(14) 0.0522(4) Uani 1 1 d . . .
H11 H 1.0710 0.9018 0.8809 0.063 Uiso 1 1 calc R . .
C12 C 0.9972(2) 0.7770(2) 0.72264(14) 0.0598(4) Uani 1 1 d . . .
H12 H 1.0507 0.8471 0.6861 0.072 Uiso 1 1 calc R . .
C14 C 0.8301(2) 0.5375(2) 0.71446(14) 0.0596(4) Uani 1 1 d . . .
H14 H 0.7712 0.4446 0.6723 0.072 Uiso 1 1 calc R . .
C13 C 0.9083(2) 0.6410(2) 0.66013(14) 0.0617(4) Uani 1 1 d . . .
H13 H 0.9010 0.6190 0.5815 0.074 Uiso 1 1 calc R . .
N1 N 0.61042(14) 0.76054(12) 1.05343(9) 0.0396(3) 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
Cl1 0.0771(3) 0.1128(4) 0.0374(2) 0.0127(2) -0.00415(19) 0.0053(3)
C7 0.0395(7) 0.0350(7) 0.0404(7) 0.0105(5) -0.0060(5) 0.0026(5)
C6 0.0437(8) 0.0356(7) 0.0440(7) 0.0129(6) 0.0005(5) 0.0038(5)
C8 0.0464(8) 0.0353(7) 0.0399(7) 0.0099(6) -0.0036(5) 0.0028(5)
C5 0.0493(8) 0.0366(7) 0.0410(7) 0.0122(6) -0.0009(6) 0.0049(5)
C4 0.0614(10) 0.0618(10) 0.0445(8) 0.0159(7) 0.0073(7) 0.0102(7)
C1 0.0487(8) 0.0565(9) 0.0471(8) 0.0131(7) -0.0080(6) 0.0068(6)
C3 0.0793(12) 0.0775(12) 0.0377(8) 0.0160(8) -0.0001(7) 0.0131(9)
C2 0.0681(11) 0.0715(11) 0.0452(8) 0.0150(8) -0.0159(7) 0.0079(8)
O1 0.0395(6) 0.0602(7) 0.0578(6) 0.0181(5) 0.0027(4) 0.0053(4)
C16 0.0389(7) 0.0371(7) 0.0388(6) 0.0099(5) -0.0033(5) 0.0085(5)
C21 0.0458(8) 0.0360(7) 0.0459(7) 0.0108(6) -0.0023(6) 0.0052(5)
C19 0.0464(8) 0.0595(9) 0.0370(7) 0.0092(6) -0.0026(6) 0.0125(6)
C17 0.0449(8) 0.0409(7) 0.0496(8) 0.0140(6) -0.0051(6) 0.0011(6)
C9 0.0410(7) 0.0459(8) 0.0455(7) 0.0118(6) -0.0033(6) 0.0050(6)
C20 0.0514(8) 0.0487(8) 0.0452(7) 0.0188(6) 0.0031(6) 0.0106(6)
C10 0.0393(7) 0.0442(8) 0.0449(7) 0.0111(6) 0.0029(5) 0.0101(5)
C15 0.0518(8) 0.0446(8) 0.0529(8) 0.0131(7) 0.0031(6) 0.0062(6)
C18 0.0475(8) 0.0472(8) 0.0505(8) 0.0054(7) -0.0094(6) 0.0000(6)
C11 0.0525(9) 0.0469(8) 0.0568(9) 0.0121(7) 0.0072(7) 0.0037(6)
C12 0.0667(10) 0.0639(11) 0.0569(9) 0.0253(8) 0.0159(8) 0.0139(8)
C14 0.0685(11) 0.0529(9) 0.0518(9) 0.0021(7) -0.0029(7) 0.0100(7)
C13 0.0714(11) 0.0718(11) 0.0451(8) 0.0142(8) 0.0058(7) 0.0226(9)
N1 0.0380(6) 0.0423(6) 0.0388(6) 0.0125(5) -0.0037(4) 0.0043(4)

_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 C19 1.7348(14) . ?
C7 C9 1.333(2) . ?
C7 N1 1.4296(17) . ?
C7 C8 1.4690(18) . ?
C6 O1 1.2169(17) . ?
C6 N1 1.3907(17) . ?
C6 C5 1.4731(19) . ?
C8 C5 1.385(2) . ?
C8 C1 1.3911(19) . ?
C5 C4 1.386(2) . ?
C4 C3 1.379(2) . ?
C1 C2 1.381(2) . ?
C3 C2 1.386(3) . ?
C16 C21 1.3807(19) . ?
C16 C17 1.3879(19) . ?
C16 N1 1.4294(16) . ?
C21 C20 1.3814(19) . ?
C19 C18 1.379(2) . ?
C19 C20 1.384(2) . ?
C17 C18 1.385(2) . ?
C9 C10 1.4759(19) . ?
C10 C15 1.384(2) . ?
C10 C11 1.397(2) . ?
C15 C14 1.381(2) . ?
C11 C12 1.379(2) . ?
C12 C13 1.372(3) . ?
C14 C13 1.374(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
C9 C7 N1 129.57(12) . . ?
C9 C7 C8 125.94(12) . . ?
N1 C7 C8 104.48(11) . . ?
O1 C6 N1 125.08(12) . . ?
O1 C6 C5 129.17(13) . . ?
N1 C6 C5 105.75(12) . . ?
C5 C8 C1 120.40(13) . . ?
C5 C8 C7 109.23(11) . . ?
C1 C8 C7 130.31(14) . . ?
C8 C5 C4 121.91(13) . . ?
C8 C5 C6 108.56(12) . . ?
C4 C5 C6 129.52(14) . . ?
C3 C4 C5 117.51(15) . . ?
C2 C1 C8 117.46(15) . . ?
C4 C3 C2 120.82(15) . . ?
C1 C2 C3 121.89(15) . . ?
C21 C16 C17 120.30(12) . . ?
C21 C16 N1 119.61(11) . . ?
C17 C16 N1 120.03(12) . . ?
C16 C21 C20 120.01(13) . . ?
C18 C19 C20 121.51(13) . . ?
C18 C19 Cl1 119.44(12) . . ?
C20 C19 Cl1 119.04(11) . . ?
C18 C17 C16 119.92(13) . . ?
C7 C9 C10 128.95(13) . . ?
C21 C20 C19 119.07(13) . . ?
C15 C10 C11 118.30(13) . . ?
C15 C10 C9 121.43(13) . . ?
C11 C10 C9 120.27(13) . . ?
C14 C15 C10 120.61(14) . . ?
C19 C18 C17 118.94(13) . . ?
C12 C11 C10 120.46(14) . . ?
C13 C12 C11 120.45(15) . . ?
C13 C14 C15 120.52(15) . . ?
C12 C13 C14 119.59(15) . . ?
C6 N1 C16 122.98(11) . . ?
C6 N1 C7 111.99(11) . . ?
C16 N1 C7 124.84(11) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 1024354'
