# 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_xv1
_database_code_depnum_ccdc_archive 'CCDC 1062570'
_audit_update_record             
;
2015-04-29 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_date             2009-06-18T19:38:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H8 Cl1 N3 O2'
_chemical_formula_sum            'C10 H8 Cl N3 O2'
_chemical_formula_weight         237.64
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.577(3)
_cell_length_b                   8.509(8)
_cell_length_c                   20.565(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.90(2)
_cell_angle_gamma                90
_cell_volume                     2145(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      16
_cell_measurement_theta_max      26
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.344
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.8455
_exptl_absorpt_correction_T_max  0.9497

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.060892
_diffrn_orient_matrix_ub_12      -0.007576
_diffrn_orient_matrix_ub_13      -0.040534
_diffrn_orient_matrix_ub_21      -0.054047
_diffrn_orient_matrix_ub_22      0.018197
_diffrn_orient_matrix_ub_23      0.028236
_diffrn_orient_matrix_ub_31      0.004607
_diffrn_orient_matrix_ub_32      0.11584
_diffrn_orient_matrix_ub_33      -0.00708
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -3 0

_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_number            4213
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4213
_reflns_number_gt                2147
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0594P)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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4213
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1297
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C11 C 0.9809(3) 1.3861(4) -0.08287(17) 0.0509(8) Uani 1 1 d . . .
C12 C 0.8187(3) 1.2710(4) -0.13605(17) 0.0547(9) Uani 1 1 d . . .
C13 C 0.8998(3) 1.2701(3) -0.07558(15) 0.0457(8) Uani 1 1 d . . .
C14 C 0.9610(3) 1.0933(4) 0.08525(16) 0.0517(9) Uani 1 1 d . . .
C15 C 0.8779(3) 0.9850(4) 0.08004(17) 0.0562(9) Uani 1 1 d . . .
H15 H 0.8285 0.968 0.0397 0.067 Uiso 1 1 calc R . .
C16 C 0.8705(3) 0.9028(4) 0.1365(2) 0.0654(10) Uani 1 1 d . . .
C17 C 0.9440(4) 0.9238(4) 0.1966(2) 0.0762(12) Uani 1 1 d . . .
H17 H 0.9378 0.8659 0.2339 0.091 Uiso 1 1 calc R . .
C18 C 1.0259(3) 1.0308(4) 0.20039(18) 0.0709(11) Uani 1 1 d . . .
H18 H 1.0758 1.0465 0.2406 0.085 Uiso 1 1 calc R . .
C19 C 1.0350(3) 1.1159(4) 0.14484(17) 0.0599(9) Uani 1 1 d . . .
H19 H 1.0911 1.1884 0.1476 0.072 Uiso 1 1 calc R . .
C22 C 0.7209(3) 1.1697(4) -0.15359(19) 0.0782(11) Uani 1 1 d . . .
H22A H 0.6783 1.1996 -0.1966 0.117 Uiso 1 1 calc R . .
H22B H 0.6781 1.1817 -0.1207 0.117 Uiso 1 1 calc R . .
H22C H 0.7431 1.062 -0.1549 0.117 Uiso 1 1 calc R . .
Cl16 Cl 0.76320(10) 0.77122(12) 0.13202(6) 0.0993(5) Uani 1 1 d . . .
N11 N 0.8400(2) 1.3731(4) -0.17794(14) 0.0714(9) Uani 1 1 d . . .
N13 N 0.8934(2) 1.1808(3) -0.02471(14) 0.0506(7) Uani 1 1 d . . .
N14 N 0.9704(2) 1.1857(3) 0.02960(13) 0.0521(7) Uani 1 1 d . . .
H14 H 1.0266 1.2447 0.0315 0.062 Uiso 1 1 calc R . .
O10 O 1.06408(19) 1.4258(3) -0.04523(12) 0.0643(7) Uani 1 1 d . . .
O11 O 0.9452(2) 1.4503(3) -0.14434(12) 0.0690(7) Uani 1 1 d . . .
C1 C 0.7136(3) 0.6564(4) -0.11221(19) 0.0635(10) Uani 1 1 d . . .
C2 C 0.5556(3) 0.5390(4) -0.17095(18) 0.0621(9) Uani 1 1 d . . .
C3 C 0.6299(3) 0.5441(4) -0.10670(17) 0.0539(9) Uani 1 1 d . . .
C4 C 0.6841(3) 0.3604(3) 0.05198(16) 0.0477(8) Uani 1 1 d . . .
C5 C 0.5937(3) 0.2635(4) 0.04601(17) 0.0589(9) Uani 1 1 d . . .
H5 H 0.5388 0.2634 0.0073 0.071 Uiso 1 1 calc R . .
C6 C 0.5875(3) 0.1677(4) 0.0990(2) 0.0621(10) Uani 1 1 d . . .
C7 C 0.6677(3) 0.1643(4) 0.15650(18) 0.0643(10) Uani 1 1 d . . .
H7 H 0.662 0.0981 0.1916 0.077 Uiso 1 1 calc R . .
C8 C 0.7562(3) 0.2607(4) 0.16105(18) 0.0614(9) Uani 1 1 d . . .
H8 H 0.8112 0.2599 0.1997 0.074 Uiso 1 1 calc R . .
C9 C 0.7652(3) 0.3591(4) 0.10915(16) 0.0528(8) Uani 1 1 d . . .
H9 H 0.8258 0.424 0.1129 0.063 Uiso 1 1 calc R . .
C21 C 0.4562(3) 0.4418(5) -0.18867(19) 0.0894(13) Uani 1 1 d . . .
H21A H 0.4031 0.4798 -0.1654 0.134 Uiso 1 1 calc R . .
H21B H 0.474 0.3346 -0.1762 0.134 Uiso 1 1 calc R . .
H21C H 0.427 0.4476 -0.2359 0.134 Uiso 1 1 calc R . .
Cl6 Cl 0.47417(10) 0.04679(13) 0.09162(6) 0.1038(4) Uani 1 1 d . . .
N1 N 0.5845(3) 0.6294(4) -0.21354(16) 0.0942(11) Uani 1 1 d . . .
N3 N 0.6201(2) 0.4560(3) -0.05679(14) 0.0516(7) Uani 1 1 d . . .
N4 N 0.6939(2) 0.4614(3) -0.00083(13) 0.0537(7) Uani 1 1 d . . .
H4 H 0.7478 0.5257 0.0037 0.064 Uiso 1 1 calc R . .
O0 O 0.7919(2) 0.6986(3) -0.07018(13) 0.0867(9) Uani 1 1 d . . .
O1 O 0.6919(2) 0.7124(3) -0.17485(13) 0.0912(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C11 O10 1.202(4) . ?
C11 O11 1.358(4) . ?
C11 C13 1.451(4) . ?
C12 N11 1.293(4) . ?
C12 C13 1.421(4) . ?
C12 C22 1.479(4) . ?
C13 N13 1.310(4) . ?
C14 C19 1.377(4) . ?
C14 C15 1.379(4) . ?
C14 N14 1.416(4) . ?
C15 C16 1.377(4) . ?
C16 C17 1.379(5) . ?
C16 Cl16 1.739(4) . ?
C17 C18 1.364(5) . ?
C18 C19 1.378(4) . ?
N11 O11 1.500(3) . ?
N13 N14 1.306(3) . ?
C1 O0 1.210(4) . ?
C1 O1 1.343(4) . ?
C1 C3 1.445(5) . ?
C2 N1 1.278(4) . ?
C2 C3 1.438(5) . ?
C2 C21 1.475(5) . ?
C3 N3 1.299(4) . ?
C4 C9 1.374(4) . ?
C4 C5 1.388(4) . ?
C4 N4 1.411(4) . ?
C5 C6 1.377(4) . ?
C6 C7 1.373(4) . ?
C6 Cl6 1.737(3) . ?
C7 C8 1.369(4) . ?
C8 C9 1.381(4) . ?
N1 O1 1.573(4) . ?
N3 N4 1.308(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
O10 C11 O11 123.0(3) . . ?
O10 C11 C13 131.0(3) . . ?
O11 C11 C13 106.0(3) . . ?
N11 C12 C13 111.9(3) . . ?
N11 C12 C22 120.9(3) . . ?
C13 C12 C22 127.2(3) . . ?
N13 C13 C12 122.9(3) . . ?
N13 C13 C11 130.3(3) . . ?
C12 C13 C11 106.8(3) . . ?
C19 C14 C15 120.8(3) . . ?
C19 C14 N14 118.7(3) . . ?
C15 C14 N14 120.5(3) . . ?
C16 C15 C14 117.8(3) . . ?
C15 C16 C17 122.1(3) . . ?
C15 C16 Cl16 118.7(3) . . ?
C17 C16 Cl16 119.2(3) . . ?
C18 C17 C16 119.0(3) . . ?
C17 C18 C19 120.3(4) . . ?
C14 C19 C18 120.0(3) . . ?
C12 N11 O11 106.2(3) . . ?
N14 N13 C13 119.9(3) . . ?
N13 N14 C14 119.6(3) . . ?
C11 O11 N11 109.1(2) . . ?
O0 C1 O1 122.6(4) . . ?
O0 C1 C3 129.1(3) . . ?
O1 C1 C3 108.3(3) . . ?
N1 C2 C3 112.7(4) . . ?
N1 C2 C21 121.6(4) . . ?
C3 C2 C21 125.7(4) . . ?
N3 C3 C2 123.5(3) . . ?
N3 C3 C1 130.0(3) . . ?
C2 C3 C1 106.4(3) . . ?
C9 C4 C5 120.5(3) . . ?
C9 C4 N4 119.2(3) . . ?
C5 C4 N4 120.2(3) . . ?
C6 C5 C4 118.2(3) . . ?
C7 C6 C5 122.2(3) . . ?
C7 C6 Cl6 119.6(3) . . ?
C5 C6 Cl6 118.2(3) . . ?
C8 C7 C6 118.4(3) . . ?
C7 C8 C9 121.1(4) . . ?
C4 C9 C8 119.6(3) . . ?
C2 N1 O1 105.5(3) . . ?
C3 N3 N4 120.1(3) . . ?
N3 N4 C4 119.3(3) . . ?
C1 O1 N1 107.1(3) . . ?

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
N11 C12 C13 N13 177.2(3) . . . . ?
C22 C12 C13 N13 -4.1(5) . . . . ?
N11 C12 C13 C11 -0.8(4) . . . . ?
C22 C12 C13 C11 178.0(3) . . . . ?
O10 C11 C13 N13 2.7(6) . . . . ?
O11 C11 C13 N13 -176.8(3) . . . . ?
O10 C11 C13 C12 -179.5(3) . . . . ?
O11 C11 C13 C12 1.0(3) . . . . ?
C19 C14 C15 C16 1.2(5) . . . . ?
N14 C14 C15 C16 -177.6(3) . . . . ?
C14 C15 C16 C17 -1.3(5) . . . . ?
C14 C15 C16 Cl16 177.5(2) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
Cl16 C16 C17 C18 -177.9(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
N14 C14 C19 C18 178.1(3) . . . . ?
C17 C18 C19 C14 0.2(5) . . . . ?
C13 C12 N11 O11 0.3(4) . . . . ?
C22 C12 N11 O11 -178.6(3) . . . . ?
C12 C13 N13 N14 -179.8(3) . . . . ?
C11 C13 N13 N14 -2.3(5) . . . . ?
C13 N13 N14 C14 177.6(3) . . . . ?
C19 C14 N14 N13 -171.2(3) . . . . ?
C15 C14 N14 N13 7.6(4) . . . . ?
O10 C11 O11 N11 179.6(3) . . . . ?
C13 C11 O11 N11 -0.9(3) . . . . ?
C12 N11 O11 C11 0.4(3) . . . . ?
N1 C2 C3 N3 -176.3(3) . . . . ?
C21 C2 C3 N3 3.4(5) . . . . ?
N1 C2 C3 C1 1.2(4) . . . . ?
C21 C2 C3 C1 -179.1(3) . . . . ?
O0 C1 C3 N3 -3.4(6) . . . . ?
O1 C1 C3 N3 176.6(3) . . . . ?
O0 C1 C3 C2 179.3(4) . . . . ?
O1 C1 C3 C2 -0.7(4) . . . . ?
C9 C4 C5 C6 0.5(5) . . . . ?
N4 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C4 C5 C6 Cl6 179.9(2) . . . . ?
C5 C6 C7 C8 0.4(5) . . . . ?
Cl6 C6 C7 C8 180.0(2) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
N4 C4 C9 C8 179.9(3) . . . . ?
C7 C8 C9 C4 0.0(5) . . . . ?
C3 C2 N1 O1 -1.2(4) . . . . ?
C21 C2 N1 O1 179.2(3) . . . . ?
C2 C3 N3 N4 176.5(3) . . . . ?
C1 C3 N3 N4 -0.4(5) . . . . ?
C3 N3 N4 C4 -177.5(3) . . . . ?
C9 C4 N4 N3 175.9(3) . . . . ?
C5 C4 N4 N3 -4.0(4) . . . . ?
O0 C1 O1 N1 -180.0(3) . . . . ?
C3 C1 O1 N1 0.0(4) . . . . ?
C2 N1 O1 C1 0.7(4) . . . . ?

####################################################################### 
# 
# 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_xv19
_database_code_depnum_ccdc_archive 'CCDC 1062571'
_audit_update_record             
;
2015-04-29 deposited with the CCDC.
2015-12-04 downloaded from the CCDC.
;

_audit_creation_date             2010-08-26T17:28:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H8 Cl1 N3 O2'
_chemical_formula_sum            'C10 H8 Cl N3 O2'
_chemical_formula_weight         237.64
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.642
_cell_length_b                   7.933
_cell_length_c                   9.511
_cell_angle_alpha                98.77
_cell_angle_beta                 104.53
_cell_angle_gamma                98.06
_cell_volume                     541.9
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      5
_cell_measurement_theta_max      16.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.34
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        Walker, N. & Stuart, D (1983) Acta. Cryst. A39, 158-166
;
_exptl_absorpt_correction_T_min  0.8477
_exptl_absorpt_correction_T_max  0.9699

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      -0.116859
_diffrn_orient_matrix_ub_12      -0.030843
_diffrn_orient_matrix_ub_13      -0.082482
_diffrn_orient_matrix_ub_21      0.069995
_diffrn_orient_matrix_ub_22      0.030963
_diffrn_orient_matrix_ub_23      -0.071203
_diffrn_orient_matrix_ub_31      0.019894
_diffrn_orient_matrix_ub_32      -0.122308
_diffrn_orient_matrix_ub_33      -0.020617
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω scans'
_diffrn_standards_number         1
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        0
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 1 -3

_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_number            2605
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_full        27.95
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             2605
_reflns_number_gt                1252
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0664P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2605
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.74111(13) 0.38640(9) 0.44365(9) 0.0952(4) Uani 1 1 d . . .
O4 O 0.2078(3) -0.1721(2) -0.05220(19) 0.0752(6) Uani 1 1 d . . .
O5 O 0.3701(3) 0.0838(2) 0.0848(2) 0.0719(6) Uani 1 1 d . . .
N1 N 0.5310(2) -0.1515(2) 0.2888(2) 0.0477(5) Uani 1 1 d . . .
N2 N 0.6057(3) 0.0113(2) 0.3446(2) 0.0488(5) Uani 1 1 d . . .
H2 H 0.572(4) 0.094(4) 0.292(3) 0.084(9) Uiso 1 1 d . . .
N3 N 0.1965(3) -0.3550(3) -0.0382(3) 0.0746(7) Uani 1 1 d . . .
C1 C 0.4074(3) -0.1869(3) 0.1618(3) 0.0456(6) Uani 1 1 d . . .
C2 C 0.3113(4) -0.3571(3) 0.0849(3) 0.0586(7) Uani 1 1 d . . .
C3 C 0.3343(5) -0.5227(3) 0.1366(4) 0.0876(10) Uani 1 1 d . . .
H3A H 0.2469 -0.6169 0.0682 0.131 Uiso 1 1 calc R . .
H3B H 0.3141 -0.5156 0.2328 0.131 Uiso 1 1 calc R . .
H3C H 0.4567 -0.5424 0.1422 0.131 Uiso 1 1 calc R . .
C5 C 0.3343(3) -0.0723(3) 0.0681(3) 0.0556(6) Uani 1 1 d . . .
C21 C 0.7382(3) 0.0568(3) 0.4816(3) 0.0498(6) Uani 1 1 d . . .
C22 C 0.8155(4) 0.2296(3) 0.5403(3) 0.0604(7) Uani 1 1 d . . .
C23 C 0.9506(4) 0.2759(4) 0.6752(3) 0.0779(9) Uani 1 1 d . . .
H23 H 1.0037 0.392 0.7139 0.094 Uiso 1 1 calc R . .
C24 C 1.0056(4) 0.1494(5) 0.7514(3) 0.0829(10) Uani 1 1 d . . .
H24 H 1.0968 0.1795 0.8412 0.099 Uiso 1 1 calc R . .
C25 C 0.9259(4) -0.0199(4) 0.6948(3) 0.0747(8) Uani 1 1 d . . .
H25 H 0.9615 -0.1047 0.7477 0.09 Uiso 1 1 calc R . .
C26 C 0.7942(3) -0.0674(4) 0.5614(3) 0.0601(7) Uani 1 1 d . . .
H26 H 0.742 -0.184 0.5241 0.072 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C22 1.732(3) . ?
O4 C5 1.351(3) . ?
O4 N3 1.470(3) . ?
O5 C5 1.207(3) . ?
N1 C1 1.296(3) . ?
N1 N2 1.307(2) . ?
N2 C21 1.395(3) . ?
N3 C2 1.279(3) . ?
C1 C2 1.431(3) . ?
C1 C5 1.440(3) . ?
C2 C3 1.488(3) . ?
C21 C26 1.383(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.391(4) . ?
C23 C24 1.377(5) . ?
C24 C25 1.360(4) . ?
C25 C26 1.369(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
C5 O4 N3 108.93(18) . . ?
C1 N1 N2 117.81(18) . . ?
N1 N2 C21 120.2(2) . . ?
C2 N3 O4 106.62(18) . . ?
N1 C1 C2 125.3(2) . . ?
N1 C1 C5 129.9(2) . . ?
C2 C1 C5 104.8(2) . . ?
N3 C2 C1 112.4(2) . . ?
N3 C2 C3 121.3(2) . . ?
C1 C2 C3 126.3(2) . . ?
O5 C5 O4 122.5(2) . . ?
O5 C5 C1 130.3(2) . . ?
O4 C5 C1 107.2(2) . . ?
C26 C21 C22 118.8(2) . . ?
C26 C21 N2 121.4(2) . . ?
C22 C21 N2 119.7(2) . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 Cl1 119.1(2) . . ?
C23 C22 Cl1 120.7(2) . . ?
C24 C23 C22 119.8(3) . . ?
C25 C24 C23 119.8(3) . . ?
C24 C25 C26 121.0(3) . . ?
C25 C26 C21 120.4(3) . . ?

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
C1 N1 N2 C21 179.4(2) . . . . ?
C5 O4 N3 C2 0.2(3) . . . . ?
N2 N1 C1 C2 -179.8(2) . . . . ?
N2 N1 C1 C5 -0.4(4) . . . . ?
O4 N3 C2 C1 -0.5(3) . . . . ?
O4 N3 C2 C3 179.0(2) . . . . ?
N1 C1 C2 N3 -180.0(2) . . . . ?
C5 C1 C2 N3 0.5(3) . . . . ?
N1 C1 C2 C3 0.6(4) . . . . ?
C5 C1 C2 C3 -178.9(3) . . . . ?
N3 O4 C5 O5 -179.8(2) . . . . ?
N3 O4 C5 C1 0.1(3) . . . . ?
N1 C1 C5 O5 0.0(5) . . . . ?
C2 C1 C5 O5 179.5(3) . . . . ?
N1 C1 C5 O4 -179.8(2) . . . . ?
C2 C1 C5 O4 -0.3(3) . . . . ?
N1 N2 C21 C26 0.1(3) . . . . ?
N1 N2 C21 C22 -179.6(2) . . . . ?
C26 C21 C22 C23 1.7(4) . . . . ?
N2 C21 C22 C23 -178.6(2) . . . . ?
C26 C21 C22 Cl1 -178.08(19) . . . . ?
N2 C21 C22 Cl1 1.6(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
Cl1 C22 C23 C24 178.9(2) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C26 1.4(5) . . . . ?
C24 C25 C26 C21 -0.5(4) . . . . ?
C22 C21 C26 C25 -1.0(4) . . . . ?
N2 C21 C26 C25 179.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl1 0.91(3) 2.52(3) 2.933(2) 108(2) .
N2 H2 O5 0.91(3) 2.16(3) 2.858(3) 133(2) .

# END of CIF
