# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_m+p21n
_database_code_depnum_ccdc_archive 'CCDC 1034368'
_audit_update_record             
;
2014-11-16 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H5 Cl4 N3 O2'
_chemical_formula_weight         352.98

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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                   7.4698(15)
_cell_length_b                   9.5364(19)
_cell_length_c                   18.730(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.05(3)
_cell_angle_gamma                90.00
_cell_volume                     1334.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1567
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.78

_exptl_crystal_description       Irregular
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8287
_exptl_absorpt_correction_T_max  0.9279
_exptl_absorpt_process_details   '(X-SHAPE and X-RED; Stoe & Cie, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'Stoe IPDS 2T image plate detector'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2344
_diffrn_reflns_av_R_equivalents  0.09
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2344
_reflns_number_gt                1743
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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 > 2σ(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)+(0.0455P)²] 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         2344
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   0.855
_refine_ls_restrained_S_all      0.855
_refine_ls_shift/su_max          0.008
_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
Cl4 Cl 0.92616(7) 0.60745(5) 0.13687(3) 0.05232(15) Uani 1 1 d . . .
Cl3 Cl 0.71290(8) 0.77507(5) 0.00486(3) 0.06201(18) Uani 1 1 d . . .
Cl1 Cl 0.79437(8) 0.13686(5) -0.02474(3) 0.05670(16) Uani 1 1 d . . .
Cl2 Cl 0.57210(9) 0.32321(7) -0.14374(3) 0.06404(18) Uani 1 1 d . . .
O1 O 1.2812(2) -0.07678(16) 0.25507(9) 0.0589(4) Uani 1 1 d . . .
O2 O 1.0804(2) -0.22624(16) 0.27585(9) 0.0659(4) Uani 1 1 d . . .
N2 N 0.9458(2) 0.30355(17) 0.11128(9) 0.0431(4) Uani 1 1 d . . .
N1 N 0.6557(2) 0.53436(17) -0.05887(9) 0.0484(4) Uani 1 1 d . . .
N3 N 1.1243(2) -0.11698(16) 0.24901(9) 0.0445(4) Uani 1 1 d . . .
C8 C 0.6692(3) 0.0165(2) 0.17080(11) 0.0489(5) Uani 1 1 d . . .
H8 H 0.5505 -0.0128 0.1699 0.059 Uiso 1 1 calc R . .
C9 C 0.8017(3) -0.0695(2) 0.20687(10) 0.0459(5) Uani 1 1 d . . .
H9 H 0.7662 -0.1522 0.2291 0.055 Uiso 1 1 calc R . .
C2 C 0.6720(3) 0.3965(2) -0.06322(10) 0.0452(5) Uani 1 1 d . . .
C4 C 0.8292(2) 0.52280(19) 0.05940(10) 0.0408(4) Uani 1 1 d . . .
C11 C 1.0308(2) 0.09033(19) 0.17592(9) 0.0388(4) Uani 1 1 d . . .
H11 H 1.1501 0.1181 0.1759 0.047 Uiso 1 1 calc R . .
C7 C 0.7143(3) 0.1386(2) 0.13850(10) 0.0445(5) Uani 1 1 d . . .
H7 H 0.6294 0.1946 0.1160 0.053 Uiso 1 1 calc R . .
C10 C 0.9806(3) -0.03028(18) 0.20871(10) 0.0376(4) Uani 1 1 d . . .
C1 C 0.7656(3) 0.3127(2) -0.00958(10) 0.0417(4) Uani 1 1 d . . .
C5 C 0.8460(2) 0.37611(18) 0.05537(10) 0.0387(4) Uani 1 1 d . . .
C3 C 0.7353(3) 0.5950(2) 0.00146(11) 0.0453(5) Uani 1 1 d . . .
C6 C 0.8949(2) 0.17570(19) 0.14074(9) 0.0377(4) Uani 1 1 d . . .
H2 H 1.013(3) 0.349(2) 0.1377(11) 0.044(6) Uiso 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
Cl4 0.0589(3) 0.0442(3) 0.0538(3) -0.0080(2) -0.0006(2) -0.0020(2)
Cl3 0.0649(4) 0.0402(3) 0.0810(4) 0.0107(3) 0.0062(3) 0.0039(2)
Cl1 0.0746(4) 0.0422(3) 0.0533(3) -0.0071(2) 0.0048(3) -0.0030(2)
Cl2 0.0784(4) 0.0722(4) 0.0415(3) 0.0038(3) -0.0075(3) -0.0203(3)
O1 0.0426(9) 0.0553(9) 0.0790(11) 0.0089(8) -0.0055(8) 0.0009(7)
O2 0.0661(10) 0.0487(9) 0.0831(11) 0.0250(8) 0.0051(8) 0.0029(8)
N2 0.0459(10) 0.0373(9) 0.0461(10) 0.0030(7) -0.0043(8) -0.0071(8)
N1 0.0477(10) 0.0497(10) 0.0478(10) 0.0115(8) 0.0045(8) -0.0060(8)
N3 0.0497(11) 0.0371(9) 0.0466(10) -0.0006(7) 0.0014(8) 0.0029(8)
C8 0.0383(11) 0.0512(11) 0.0572(12) 0.0030(10) 0.0084(9) -0.0041(9)
C9 0.0478(12) 0.0395(10) 0.0503(12) 0.0042(9) 0.0081(9) -0.0042(9)
C2 0.0437(11) 0.0520(12) 0.0399(11) 0.0046(9) 0.0065(8) -0.0108(9)
C4 0.0391(11) 0.0407(10) 0.0424(11) 0.0002(8) 0.0077(8) -0.0043(8)
C11 0.0369(10) 0.0388(9) 0.0406(10) -0.0028(8) 0.0032(8) -0.0028(8)
C7 0.0395(11) 0.0458(11) 0.0481(11) 0.0034(9) 0.0019(8) 0.0053(9)
C10 0.0412(11) 0.0336(9) 0.0380(10) -0.0022(7) 0.0020(8) 0.0025(8)
C1 0.0439(11) 0.0394(10) 0.0420(10) 0.0016(8) 0.0080(9) -0.0067(8)
C5 0.0357(10) 0.0392(10) 0.0413(10) 0.0031(8) 0.0069(8) -0.0029(8)
C3 0.0402(11) 0.0400(10) 0.0556(12) 0.0079(9) 0.0113(9) -0.0010(8)
C6 0.0421(11) 0.0352(9) 0.0358(9) -0.0012(8) 0.0031(8) -0.0010(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl4 C4 1.811(2) . ?
Cl3 C3 1.726(2) . ?
Cl1 C1 1.714(2) . ?
Cl2 C2 1.821(2) . ?
O1 N3 1.239(2) . ?
O2 N3 1.202(2) . ?
N2 C6 1.391(2) . ?
N2 C5 1.459(3) . ?
N2 H2 0.82(2) . ?
N1 C2 1.323(3) . ?
N1 C3 1.401(3) . ?
N3 C10 1.550(3) . ?
C8 C7 1.354(3) . ?
C8 C9 1.453(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C2 C1 1.462(3) . ?
C4 C5 1.407(3) . ?
C4 C3 1.464(3) . ?
C11 C10 1.357(2) . ?
C11 C6 1.458(3) . ?
C11 H11 0.9300 . ?
C7 C6 1.396(3) . ?
C7 H7 0.9300 . ?
C1 C5 1.485(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
C6 N2 C5 124.12(17) . . ?
C6 N2 H2 112.6(15) . . ?
C5 N2 H2 119.5(15) . . ?
C2 N1 C3 114.90(17) . . ?
O2 N3 O1 119.20(17) . . ?
O2 N3 C10 118.50(17) . . ?
O1 N3 C10 122.29(15) . . ?
C7 C8 C9 121.57(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 120.99(17) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
N1 C2 C1 123.03(18) . . ?
N1 C2 Cl2 113.25(15) . . ?
C1 C2 Cl2 123.70(15) . . ?
C5 C4 C3 118.09(18) . . ?
C5 C4 Cl4 116.79(15) . . ?
C3 C4 Cl4 125.12(15) . . ?
C10 C11 C6 119.05(17) . . ?
C10 C11 H11 120.5 . . ?
C6 C11 H11 120.5 . . ?
C8 C7 C6 116.47(18) . . ?
C8 C7 H7 121.8 . . ?
C6 C7 H7 121.8 . . ?
C11 C10 C9 118.93(17) . . ?
C11 C10 N3 118.75(16) . . ?
C9 C10 N3 122.28(16) . . ?
C2 C1 C5 122.23(17) . . ?
C2 C1 Cl1 118.75(15) . . ?
C5 C1 Cl1 118.91(14) . . ?
C4 C5 N2 118.59(17) . . ?
C4 C5 C1 114.40(17) . . ?
N2 C5 C1 126.92(16) . . ?
N1 C3 C4 127.32(17) . . ?
N1 C3 Cl3 113.53(15) . . ?
C4 C3 Cl3 119.14(16) . . ?
N2 C6 C7 118.34(17) . . ?
N2 C6 C11 118.59(17) . . ?
C7 C6 C11 122.98(17) . . ?

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
C7 C8 C9 C10 -0.8(3) . . . . ?
C3 N1 C2 C1 0.0(3) . . . . ?
C3 N1 C2 Cl2 -178.33(12) . . . . ?
C9 C8 C7 C6 1.1(3) . . . . ?
C6 C11 C10 C9 0.9(3) . . . . ?
C6 C11 C10 N3 -177.21(15) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 N3 177.79(17) . . . . ?
O2 N3 C10 C11 -177.44(17) . . . . ?
O1 N3 C10 C11 3.4(3) . . . . ?
O2 N3 C10 C9 4.6(3) . . . . ?
O1 N3 C10 C9 -174.61(17) . . . . ?
N1 C2 C1 C5 1.7(3) . . . . ?
Cl2 C2 C1 C5 179.77(13) . . . . ?
N1 C2 C1 Cl1 -174.55(15) . . . . ?
Cl2 C2 C1 Cl1 3.6(2) . . . . ?
C3 C4 C5 N2 177.51(15) . . . . ?
Cl4 C4 C5 N2 -2.7(2) . . . . ?
C3 C4 C5 C1 0.7(2) . . . . ?
Cl4 C4 C5 C1 -179.47(12) . . . . ?
C6 N2 C5 C4 140.09(18) . . . . ?
C6 N2 C5 C1 -43.6(3) . . . . ?
C2 C1 C5 C4 -1.9(2) . . . . ?
Cl1 C1 C5 C4 174.28(13) . . . . ?
C2 C1 C5 N2 -178.39(16) . . . . ?
Cl1 C1 C5 N2 -2.2(2) . . . . ?
C2 N1 C3 C4 -1.3(3) . . . . ?
C2 N1 C3 Cl3 179.49(14) . . . . ?
C5 C4 C3 N1 0.9(3) . . . . ?
Cl4 C4 C3 N1 -178.91(14) . . . . ?
C5 C4 C3 Cl3 -179.90(13) . . . . ?
Cl4 C4 C3 Cl3 0.3(2) . . . . ?
C5 N2 C6 C7 -25.0(3) . . . . ?
C5 N2 C6 C11 158.32(17) . . . . ?
C8 C7 C6 N2 -176.90(17) . . . . ?
C8 C7 C6 C11 -0.4(3) . . . . ?
C10 C11 C6 N2 175.91(16) . . . . ?
C10 C11 C6 C7 -0.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.043
#==========
#END OF CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
