# 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_0
_database_code_depnum_ccdc_archive 'CCDC 1422567'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 Cl N3 O'
_chemical_formula_weight         380.88

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                   9.4578(5)
_cell_length_b                   9.4805(5)
_cell_length_c                   11.6473(6)
_cell_angle_alpha                111.339(3)
_cell_angle_beta                 91.870(3)
_cell_angle_gamma                99.568(3)
_cell_volume                     954.28(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             402
_exptl_absorpt_coefficient_mu    0.217
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_process_details   ?

_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  MoKα
_diffrn_measurement_method       'sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4583
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3338
_reflns_number_gt                2857
_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)+(0.1400P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.2092
_refine_ls_wR_factor_gt          0.1984
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_restrained_S_all      1.280
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

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 0.44391(6) 0.33623(8) 0.27302(7) 0.0732(3) Uani 1 1 d . . .
N1 N -0.0585(2) 0.2182(2) 0.04822(15) 0.0526(5) Uani 1 1 d . . .
N2 N -0.17629(18) 0.23172(18) 0.42560(14) 0.0403(4) Uani 1 1 d . . .
N3 N -0.17245(18) 0.37599(17) 0.41559(14) 0.0405(4) Uani 1 1 d . . .
H3A H -0.2131 0.4486 0.4613 0.049 Uiso 1 1 calc R . .
O1 O -0.0784(2) 0.01467(17) 0.32880(15) 0.0639(5) Uani 1 1 d . . .
C3 C 0.1790(2) 0.2847(2) 0.15486(18) 0.0447(5) Uani 1 1 d . . .
C5 C -0.0979(2) 0.3804(2) 0.32663(15) 0.0371(4) Uani 1 1 d . . .
C6 C -0.2605(2) 0.1963(2) 0.51384(16) 0.0405(5) Uani 1 1 d . . .
C7 C -0.0429(2) 0.2348(2) 0.26405(16) 0.0393(5) Uani 1 1 d . . .
C8 C -0.0697(3) 0.5209(2) 0.29413(18) 0.0479(5) Uani 1 1 d . . .
H8A H -0.0970 0.4902 0.2062 0.058 Uiso 1 1 calc R . .
H8B H 0.0331 0.5624 0.3093 0.058 Uiso 1 1 calc R . .
C10 C 0.0859(2) 0.2689(2) 0.05154(17) 0.0477(5) Uani 1 1 d . . .
C11 C -0.0983(2) 0.1421(2) 0.34198(17) 0.0423(5) Uani 1 1 d . . .
C12 C -0.1125(2) 0.1412(2) 0.12961(17) 0.0441(5) Uani 1 1 d . . .
H12A H -0.0866 0.0389 0.1016 0.053 Uiso 1 1 calc R . .
C13 C 0.1207(2) 0.2523(3) 0.26420(18) 0.0470(5) Uani 1 1 d . . .
H13A H 0.1656 0.3357 0.3400 0.056 Uiso 1 1 calc R . .
H13B H 0.1481 0.1583 0.2646 0.056 Uiso 1 1 calc R . .
C14 C 0.3248(3) 0.3270(3) 0.1511(2) 0.0563(6) Uani 1 1 d . . .
C15 C -0.3592(3) 0.2862(3) 0.5668(2) 0.0561(6) Uani 1 1 d . . .
H15A H -0.3689 0.3706 0.5465 0.067 Uiso 1 1 calc R . .
C16 C -0.2459(3) 0.0711(3) 0.5443(2) 0.0583(6) Uani 1 1 d . . .
H16A H -0.1780 0.0114 0.5101 0.070 Uiso 1 1 calc R . .
C17 C 0.1438(3) 0.3058(3) -0.0455(2) 0.0669(7) Uani 1 1 d . . .
H17A H 0.0829 0.3006 -0.1118 0.080 Uiso 1 1 calc R . .
C18 C 0.3815(3) 0.3604(3) 0.0534(3) 0.0774(8) Uani 1 1 d . . .
H18A H 0.4805 0.3896 0.0539 0.093 Uiso 1 1 calc R . .
C19 C -0.4324(3) 0.1231(4) 0.6782(2) 0.0678(7) Uani 1 1 d . . .
H19A H -0.4920 0.0970 0.7322 0.081 Uiso 1 1 calc R . .
C20 C -0.3341(3) 0.0362(3) 0.6267(2) 0.0691(7) Uani 1 1 d . . .
H20A H -0.3256 -0.0484 0.6471 0.083 Uiso 1 1 calc R . .
C21 C -0.2752(3) 0.1214(3) 0.1073(2) 0.0620(6) Uani 1 1 d . . .
H21A H -0.3093 0.2098 0.1638 0.074 Uiso 1 1 calc R . .
H21B H -0.3237 0.0291 0.1179 0.074 Uiso 1 1 calc R . .
C22 C -0.1665(3) 0.1988(3) -0.0508(2) 0.0646(7) Uani 1 1 d . . .
H22A H -0.1369 0.1426 -0.1310 0.077 Uiso 1 1 calc R . .
H22B H -0.1825 0.2982 -0.0487 0.077 Uiso 1 1 calc R . .
C23 C -0.1486(3) 0.6476(2) 0.3650(2) 0.0582(6) Uani 1 1 d . . .
H23A H -0.1252 0.7328 0.3386 0.087 Uiso 1 1 calc R . .
H23B H -0.1200 0.6816 0.4521 0.087 Uiso 1 1 calc R . .
H23C H -0.2506 0.6087 0.3492 0.087 Uiso 1 1 calc R . .
C24 C -0.4436(3) 0.2496(3) 0.6502(2) 0.0728(7) Uani 1 1 d . . .
H24A H -0.5087 0.3114 0.6879 0.087 Uiso 1 1 calc R . .
C25 C 0.2898(4) 0.3495(3) -0.0430(3) 0.0806(9) Uani 1 1 d . . .
H25A H 0.3269 0.3721 -0.1087 0.097 Uiso 1 1 calc R . .
C26 C -0.3012(3) 0.1083(3) -0.0260(2) 0.0756(8) Uani 1 1 d . . .
H26A H -0.3172 0.0012 -0.0821 0.091 Uiso 1 1 calc R . .
H26B H -0.3847 0.1512 -0.0366 0.091 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 1.750(3) . ?
N1 C10 1.365(3) . ?
N1 C12 1.451(3) . ?
N1 C22 1.454(3) . ?
N2 C11 1.366(3) . ?
N2 N3 1.409(2) . ?
N2 C6 1.421(2) . ?
N3 C5 1.281(2) . ?
O1 C11 1.208(2) . ?
C3 C14 1.377(3) . ?
C3 C10 1.415(3) . ?
C3 C13 1.515(3) . ?
C5 C7 1.496(2) . ?
C5 C8 1.498(3) . ?
C6 C15 1.377(3) . ?
C6 C16 1.383(3) . ?
C7 C11 1.527(3) . ?
C7 C13 1.528(3) . ?
C7 C12 1.549(3) . ?
C8 C23 1.517(3) . ?
C10 C17 1.402(3) . ?
C12 C21 1.521(3) . ?
C14 C18 1.389(4) . ?
C15 C24 1.380(3) . ?
C16 C20 1.385(3) . ?
C17 C25 1.371(4) . ?
C18 C25 1.359(4) . ?
C19 C20 1.354(4) . ?
C19 C24 1.372(4) . ?
C21 C26 1.520(4) . ?
C22 C26 1.511(4) . ?

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 N1 C12 120.41(16) . . ?
C10 N1 C22 125.36(18) . . ?
C12 N1 C22 112.51(18) . . ?
C11 N2 N3 112.35(14) . . ?
C11 N2 C6 129.13(15) . . ?
N3 N2 C6 118.48(15) . . ?
C5 N3 N2 108.23(15) . . ?
C14 C3 C10 117.61(19) . . ?
C14 C3 C13 121.19(19) . . ?
C10 C3 C13 121.18(18) . . ?
N3 C5 C7 112.95(15) . . ?
N3 C5 C8 121.55(16) . . ?
C7 C5 C8 125.49(16) . . ?
C15 C6 C16 120.28(19) . . ?
C15 C6 N2 119.25(17) . . ?
C16 C6 N2 120.46(19) . . ?
C5 C7 C11 100.85(14) . . ?
C5 C7 C13 115.88(16) . . ?
C11 C7 C13 110.43(15) . . ?
C5 C7 C12 113.90(15) . . ?
C11 C7 C12 106.80(15) . . ?
C13 C7 C12 108.41(15) . . ?
C5 C8 C23 114.70(17) . . ?
N1 C10 C17 121.2(2) . . ?
N1 C10 C3 119.47(17) . . ?
C17 C10 C3 119.3(2) . . ?
O1 C11 N2 128.31(18) . . ?
O1 C11 C7 126.14(18) . . ?
N2 C11 C7 105.53(15) . . ?
N1 C12 C21 103.43(17) . . ?
N1 C12 C7 110.06(16) . . ?
C21 C12 C7 116.83(17) . . ?
C3 C13 C7 114.18(16) . . ?
C3 C14 C18 122.6(2) . . ?
C3 C14 Cl1 118.85(18) . . ?
C18 C14 Cl1 118.5(2) . . ?
C6 C15 C24 119.3(2) . . ?
C6 C16 C20 118.8(2) . . ?
C25 C17 C10 120.3(2) . . ?
C25 C18 C14 118.8(3) . . ?
C20 C19 C24 119.7(2) . . ?
C19 C20 C16 121.2(2) . . ?
C12 C21 C26 104.2(2) . . ?
N1 C22 C26 104.8(2) . . ?
C19 C24 C15 120.6(3) . . ?
C18 C25 C17 121.3(2) . . ?
C22 C26 C21 105.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.062
