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

 
data_t 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C H Cl N O' 
_chemical_formula_weight          78.48 
 
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            ? 
_symmetry_space_group_name_H-M    ? 
 
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                    7.240(6) 
_cell_length_b                    11.439(10) 
_cell_length_c                    29.79(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2467(4) 
_cell_formula_units_Z             32 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.690 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1248 
_exptl_absorpt_coefficient_mu     0.963 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6405 
_diffrn_reflns_av_R_equivalents   0.0654 
_diffrn_reflns_av_sigmaI/netI     0.0279 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        5 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          2.74 
_diffrn_reflns_theta_max          17.19 
_reflns_number_total              735 
_reflns_number_gt                 591 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.0577P)²+0.2292P] 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          735 
_refine_ls_number_parameters      173 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0435 
_refine_ls_R_factor_gt            0.0300 
_refine_ls_wR_factor_ref          0.0823 
_refine_ls_wR_factor_gt           0.0756 
_refine_ls_goodness_of_fit_ref    1.019 
_refine_ls_restrained_S_all       1.019 
_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 0.46554(17) 1.20625(10) 0.39949(4) 0.0590(6) Uani 1 1 d . . . 
N1 N 0.2834(5) 0.8829(3) 0.2575(2) 0.0380(11) Uani 1 1 d . . . 
N2 N 0.3784(5) 1.0630(5) 0.28184(18) 0.0286(10) Uani 1 1 d . . . 
N3 N 0.3191(5) 0.9129(3) 0.3364(2) 0.0388(11) Uani 1 1 d . . . 
C1 C 0.3195(6) 0.9551(6) 0.2212(2) 0.0313(13) Uani 1 1 d . . . 
C2 C 0.3100(6) 0.9313(4) 0.1753(2) 0.0399(13) Uani 1 1 d . . . 
H2 H 0.2685 0.8593 0.1650 0.048 Uiso 1 1 calc R . . 
C3 C 0.3636(6) 1.0174(6) 0.14591(16) 0.0443(14) Uani 1 1 d . . . 
H3 H 0.3585 1.0027 0.1152 0.053 Uiso 1 1 calc R . . 
C4 C 0.4259(6) 1.1268(5) 0.1609(2) 0.0450(14) Uani 1 1 d . . . 
H4 H 0.4630 1.1824 0.1400 0.054 Uiso 1 1 calc R . . 
C5 C 0.4333(6) 1.1534(4) 0.2059(2) 0.0364(13) Uani 1 1 d . . . 
H5 H 0.4726 1.2261 0.2161 0.044 Uiso 1 1 calc R . . 
C6 C 0.3788(6) 1.0658(6) 0.2351(2) 0.0299(13) Uani 1 1 d . . . 
C7 C 0.3222(6) 0.9487(6) 0.2927(3) 0.0330(13) Uani 1 1 d . . . 
C8 C 0.4191(5) 1.1437(4) 0.3141(3) 0.0347(14) Uani 1 1 d . . . 
H8 H 0.4511 1.2200 0.3066 0.042 Uiso 1 1 calc R . . 
C9 C 0.4111(5) 1.1082(5) 0.35765(19) 0.0338(13) Uani 1 1 d . . . 
C10 C 0.3634(6) 0.9902(6) 0.3670(2) 0.0353(13) Uani 1 1 d . . . 
C11 C 0.3599(10) 0.9495(5) 0.4154(2) 0.0504(15) Uani 1 1 d . . . 
C12 C 0.5278(9) 0.8397(6) 0.46954(17) 0.112(2) Uani 1 1 d . . . 
H12A H 0.6370 0.8730 0.4834 0.134 Uiso 1 1 calc R . . 
H12B H 0.4215 0.8612 0.4875 0.134 Uiso 1 1 calc R . . 
C13 C 0.5445(9) 0.7138(6) 0.46799(16) 0.100(2) Uani 1 1 d . . . 
H13A H 0.4289 0.6804 0.4588 0.150 Uiso 1 1 calc R . . 
H13B H 0.5766 0.6850 0.4972 0.150 Uiso 1 1 calc R . . 
H13C H 0.6390 0.6925 0.4469 0.150 Uiso 1 1 calc R . . 
O1 O 0.2398(6) 0.9715(3) 0.44104(12) 0.0855(14) Uani 1 1 d . . . 
O2 O 0.5068(6) 0.8860(4) 0.42416(12) 0.0838(13) 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 0.0783(11) 0.0490(10) 0.0496(9) -0.0072(7) -0.0077(7) -0.0045(8) 
N1 0.041(3) 0.026(3) 0.047(3) -0.007(4) -0.003(2) -0.006(2) 
N2 0.027(3) 0.016(4) 0.042(5) 0.005(4) -0.002(2) -0.003(2) 
N3 0.039(3) 0.026(3) 0.052(4) -0.001(4) 0.003(2) -0.004(2) 
C1 0.030(3) 0.013(5) 0.052(6) 0.001(5) -0.002(3) 0.001(3) 
C2 0.041(4) 0.039(5) 0.040(4) -0.016(4) -0.008(3) 0.001(3) 
C3 0.052(4) 0.047(4) 0.034(3) 0.007(4) 0.001(3) 0.011(3) 
C4 0.043(4) 0.033(5) 0.059(5) 0.008(3) -0.002(3) 0.002(3) 
C5 0.039(3) 0.032(4) 0.039(4) -0.005(4) -0.007(3) 0.003(3) 
C6 0.025(3) 0.031(6) 0.034(5) 0.009(5) 0.000(3) 0.005(3) 
C7 0.025(3) 0.031(6) 0.043(6) 0.013(5) -0.001(3) 0.002(3) 
C8 0.026(3) 0.016(4) 0.062(5) -0.014(4) -0.009(3) -0.002(2) 
C9 0.041(3) 0.035(5) 0.025(4) -0.001(3) -0.006(2) 0.007(3) 
C10 0.038(3) 0.024(5) 0.044(5) 0.010(5) 0.002(3) 0.002(3) 
C11 0.058(5) 0.040(4) 0.053(6) 0.003(3) 0.004(4) 0.001(4) 
C12 0.164(7) 0.123(7) 0.048(5) 0.034(4) -0.004(4) 0.037(5) 
C13 0.139(6) 0.096(6) 0.065(5) 0.026(4) -0.010(4) -0.007(5) 
O1 0.093(3) 0.100(3) 0.064(3) 0.013(2) 0.033(2) 0.029(3) 
O2 0.091(3) 0.109(3) 0.051(3) 0.029(2) 0.006(2) 0.042(3) 
 
_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 C9 1.722(4) . ? 
N1 C7 1.320(5) . ? 
N1 C1 1.387(5) . ? 
N2 C8 1.365(5) . ? 
N2 C6 1.392(5) . ? 
N2 C7 1.406(5) . ? 
N3 C10 1.310(5) . ? 
N3 C7 1.366(5) . ? 
C1 C2 1.395(6) . ? 
C1 C6 1.400(6) . ? 
C2 C3 1.374(5) . ? 
C2 H2 0.9300 . ? 
C3 C4 1.404(6) . ? 
C3 H3 0.9300 . ? 
C4 C5 1.375(5) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.384(6) . ? 
C5 H5 0.9300 . ? 
C8 C9 1.360(5) . ? 
C8 H8 0.9300 . ? 
C9 C10 1.421(6) . ? 
C10 C11 1.514(6) . ? 
C11 O1 1.184(5) . ? 
C11 O2 1.314(6) . ? 
C12 C13 1.445(7) . ? 
C12 O2 1.460(5) . ? 
C12 H12A 0.9700 . ? 
C12 H12B 0.9700 . ? 
C13 H13A 0.9600 . ? 
C13 H13B 0.9600 . ? 
C13 H13C 0.9600 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C7 N1 C1 103.8(4) . . ? 
C8 N2 C6 133.4(6) . . ? 
C8 N2 C7 122.0(5) . . ? 
C6 N2 C7 104.6(5) . . ? 
C10 N3 C7 117.2(4) . . ? 
N1 C1 C2 129.7(7) . . ? 
N1 C1 C6 111.5(5) . . ? 
C2 C1 C6 118.8(6) . . ? 
C3 C2 C1 118.1(4) . . ? 
C3 C2 H2 120.9 . . ? 
C1 C2 H2 120.9 . . ? 
C2 C3 C4 121.7(4) . . ? 
C2 C3 H3 119.1 . . ? 
C4 C3 H3 119.1 . . ? 
C5 C4 C3 121.4(4) . . ? 
C5 C4 H4 119.3 . . ? 
C3 C4 H4 119.3 . . ? 
C6 C5 C4 116.2(4) . . ? 
C6 C5 H5 121.9 . . ? 
C4 C5 H5 121.9 . . ? 
C5 C6 N2 130.3(7) . . ? 
C5 C6 C1 123.7(6) . . ? 
N2 C6 C1 105.9(5) . . ? 
N1 C7 N3 125.6(7) . . ? 
N1 C7 N2 114.2(6) . . ? 
N3 C7 N2 120.2(6) . . ? 
N2 C8 C9 117.4(4) . . ? 
N2 C8 H8 121.3 . . ? 
C9 C8 H8 121.3 . . ? 
C8 C9 C10 118.8(4) . . ? 
C8 C9 Cl1 119.1(6) . . ? 
C10 C9 Cl1 122.1(5) . . ? 
N3 C10 C9 124.3(4) . . ? 
N3 C10 C11 116.7(6) . . ? 
C9 C10 C11 118.9(6) . . ? 
O1 C11 O2 125.7(5) . . ? 
O1 C11 C10 124.1(6) . . ? 
O2 C11 C10 110.2(5) . . ? 
C13 C12 O2 109.9(5) . . ? 
C13 C12 H12A 109.7 . . ? 
O2 C12 H12A 109.7 . . ? 
C13 C12 H12B 109.7 . . ? 
O2 C12 H12B 109.7 . . ? 
H12A C12 H12B 108.2 . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C11 O2 C12 117.9(4) . . ? 
 
_diffrn_measured_fraction_theta_max    0.996 
_diffrn_reflns_theta_full              17.19 
_diffrn_measured_fraction_theta_full   0.996 
_refine_diff_density_max    0.161 
_refine_diff_density_min   -0.118 
_refine_diff_density_rms    0.029 
