# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_br4q_4ampy_100k_2
_database_code_depnum_ccdc_archive 'CCDC 1921856'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2019-03-26T15:38:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C21 H9 Br8 N2 O5'
_chemical_formula_moiety         '2(C6 Br4 O2), 2(C1.50 O0.50), C6 H9 N2'
_chemical_formula_weight         1008.50

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   3.7890(2)
_cell_length_b                   12.3018(9)
_cell_length_c                   13.8689(9)
_cell_angle_alpha                91.145(6)
_cell_angle_beta                 91.064(5)
_cell_angle_gamma                92.337(5)
_cell_volume                     645.66(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3025
_cell_measurement_theta_min      3.574
_cell_measurement_theta_max      75.928
_cell_measurement_temperature    100(2)
_exptl_crystal_description       rod
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    2.594
_exptl_crystal_F_000             443
_exptl_absorpt_coefficient_mu    15.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.44844
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            4871
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_theta_min         3.188
_diffrn_reflns_theta_max         76.246
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2660
_reflns_number_gt                2423
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.094
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.07
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     182
_refine_ls_number_restraints     31
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0538P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0009(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1A 0.25420(12) 0.23110(4) 0.09607(3) 0.02830(15) Uani d 1 . . Br
Br2A 0.21599(12) 0.18602(4) -0.14643(3) 0.02828(15) Uani d 1 . . Br
O1A 0.5346(12) 0.0359(3) 0.1918(2) 0.0421(9) Uani d 1 . . O
C1A 0.5182(13) 0.0192(3) 0.1045(3) 0.0282(9) Uani d 1 . . C
C2A 0.3913(12) 0.1008(3) 0.0378(3) 0.0250(8) Uani d 1 . . C
C3A 0.3770(12) 0.0829(3) -0.0586(3) 0.0244(8) Uani d 1 . . C
Br1B 0.77329(10) 0.34774(3) 0.68300(3) 0.02246(14) Uani d 1 . . Br
Br2B 1.24093(11) 0.59085(3) 0.71716(3) 0.02403(15) Uani d 1 . . Br
O1B 0.5827(9) 0.3191(2) 0.4750(2) 0.0307(7) Uani d 1 . . O
C1B 0.7807(11) 0.4007(3) 0.4864(3) 0.0229(8) Uani d 1 . . C
C2B 0.9066(11) 0.4389(3) 0.5816(3) 0.0216(8) Uani d 1 . . C
C3B 1.1009(11) 0.5335(3) 0.5954(3) 0.0205(7) Uani d 1 . . C
N1 0.0771(10) 0.0744(3) 0.4289(3) 0.0231(7) Uani d 0.5 . . N
C4 0.1436(12) 0.1013(3) 0.5255(3) 0.0254(8) Uani d 1 . . C
H4 0.239927 0.169778 0.542922 0.03 Uiso calc 1 . . H
C5 -0.0673(12) -0.0270(3) 0.4049(3) 0.0255(8) Uani d 1 . . C
H5 -0.113863 -0.045429 0.34043 0.031 Uiso calc 1 . . H
C6 0.0771(10) 0.0744(3) 0.4289(3) 0.0231(7) Uani d 0.5 . . C
C7 0.1642(14) 0.1501(3) 0.3574(3) 0.0327(10) Uani d 0.5 . . C
H7A 0.261366 0.215936 0.387447 0.049 Uiso calc 0.5 . . H
H7B 0.335132 0.120216 0.315242 0.049 Uiso calc 0.5 . . H
H7C -0.044575 0.165736 0.320837 0.049 Uiso calc 0.5 . . H
N2 0.1642(14) 0.1501(3) 0.3574(3) 0.0327(10) Uani d 0.5 . . N
H2A 0.127088 0.133186 0.297516 0.049 Uiso calc 0.5 . . H
H2B 0.254457 0.213235 0.373668 0.049 Uiso calc 0.5 . . H
O2 -0.229(5) 0.4676(8) -0.0573(8) 0.075(4) Uani d 0.5 . . O
C8 -0.198(5) 0.5129(10) 0.0226(9) 0.077(4) Uani d 0.5 . . C
C9 -0.489(8) 0.5464(18) 0.0855(17) 0.110(7) Uani d 0.5 . . C
C10 0.123(8) 0.554(3) 0.080(2) 0.157(12) Uani d 0.5 . . C



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C2A . 1.877(4) ?
Br2A C3A . 1.887(4) ?
O1A C1A . 1.223(6) ?
C1A C2A . 1.469(6) ?
C1A C3A 2_655 1.469(6) ?
C2A C3A . 1.350(6) ?
Br1B C2B . 1.880(4) ?
Br2B C3B . 1.876(4) ?
O1B C1B . 1.235(5) ?
C1B C2B . 1.458(6) ?
C1B C3B 2_766 1.472(6) ?
C2B C3B . 1.359(5) ?
N1 C5 . 1.373(6) ?
N1 C4 . 1.390(6) ?
N1 N2 . 1.409(5) ?
C4 C5 2_556 1.369(6) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
N2 H2A . 0.86 ?
N2 H2B . 0.86 ?
O2 C10 2_565 0.59(4) ?
O2 C9 2_465 1.14(3) ?
O2 C8 . 1.232(13) ?
O2 C8 2_565 1.69(3) ?
C8 C9 . 1.483(16) ?
C8 C10 . 1.506(18) ?
C8 C10 2_565 1.67(4) ?
C8 C8 2_565 1.68(4) ?
C8 C9 2_465 2.00(4) ?
C9 C10 1_455 1.48(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
O1A C1A C2A 121.9(4) . . ?
O1A C1A C3A 123.0(4) . 2_655 ?
C2A C1A C3A 115.0(4) . 2_655 ?
C3A C2A C1A 122.0(4) . . ?
C3A C2A Br1A 122.8(3) . . ?
C1A C2A Br1A 115.2(3) . . ?
C2A C3A C1A 123.0(4) . 2_655 ?
C2A C3A Br2A 123.1(3) . . ?
C1A C3A Br2A 113.9(3) 2_655 . ?
O1B C1B C2B 122.1(4) . . ?
O1B C1B C3B 121.9(4) . 2_766 ?
C2B C1B C3B 116.0(3) . 2_766 ?
C3B C2B C1B 122.4(4) . . ?
C3B C2B Br1B 123.1(3) . . ?
C1B C2B Br1B 114.5(3) . . ?
C2B C3B C1B 121.5(4) . 2_766 ?
C2B C3B Br2B 123.9(3) . . ?
C1B C3B Br2B 114.6(3) 2_766 . ?
C5 N1 C4 119.0(4) . . ?
C5 N1 N2 121.2(4) . . ?
C4 N1 N2 119.8(4) . . ?
C5 C4 N1 120.0(4) 2_556 . ?
C5 C4 H4 120 2_556 . ?
N1 C4 H4 120 . . ?
C4 C5 N1 121.0(4) 2_556 . ?
C4 C5 H5 119.5 2_556 . ?
N1 C5 H5 119.5 . . ?
N1 N2 H2A 120 . . ?
N1 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
C10 O2 C9 114(3) 2_565 2_465 ?
C10 O2 C8 129(4) 2_565 . ?
C9 O2 C8 115.3(19) 2_465 . ?
C10 O2 C8 62(3) 2_565 2_565 ?
C9 O2 C8 176.4(17) 2_465 2_565 ?
C8 O2 C8 68.1(14) . 2_565 ?
O2 C8 C9 126.7(16) . . ?
O2 C8 C10 131.7(18) . . ?
C9 C8 C10 101.6(15) . . ?
O2 C8 C10 15.8(13) . 2_565 ?
C9 C8 C10 141.9(19) . 2_565 ?
C10 C8 C10 116.5(16) . 2_565 ?
O2 C8 C8 68.9(12) . 2_565 ?
C9 C8 C8 164.4(19) . 2_565 ?
C10 C8 C8 62.9(17) . 2_565 ?
C10 C8 C8 53.5(11) 2_565 2_565 ?
O2 C8 O2 111.9(14) . 2_565 ?
C9 C8 O2 121.4(15) . 2_565 ?
C10 C8 O2 20.2(15) . 2_565 ?
C10 C8 O2 96.4(16) 2_565 2_565 ?
C8 C8 O2 43.0(9) 2_565 2_565 ?
O2 C8 C9 30.9(10) . 2_465 ?
C9 C8 C9 95.8(14) . 2_465 ?
C10 C8 C9 162.2(17) . 2_465 ?
C10 C8 C9 46.5(11) 2_565 2_465 ?
C8 C8 C9 99.8(12) 2_565 2_465 ?
O2 C8 C9 142.8(13) 2_565 2_465 ?
O2 C9 C10 21.1(15) 2_465 1_455 ?
O2 C9 C8 118(2) 2_465 . ?
C10 C9 C8 139(3) 1_455 . ?
O2 C9 C8 33.8(12) 2_465 2_465 ?
C10 C9 C8 55(2) 1_455 2_465 ?
C8 C9 C8 84.2(14) . 2_465 ?
O2 C10 C9 44(3) 2_565 1_655 ?
O2 C10 C8 97(4) 2_565 . ?
C9 C10 C8 142(3) 1_655 . ?
O2 C10 C8 35(3) 2_565 2_565 ?
C9 C10 C8 79(3) 1_655 2_565 ?
C8 C10 C8 63.5(16) . 2_565 ?

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
O1A C1A C2A C3A 179.2(5) . . . . ?
C3A C1A C2A C3A -0.7(7) 2_655 . . . ?
O1A C1A C2A Br1A -0.5(6) . . . . ?
C3A C1A C2A Br1A 179.6(3) 2_655 . . . ?
C1A C2A C3A C1A 0.8(7) . . . 2_655 ?
Br1A C2A C3A C1A -179.6(3) . . . 2_655 ?
C1A C2A C3A Br2A -179.9(3) . . . . ?
Br1A C2A C3A Br2A -0.3(5) . . . . ?
O1B C1B C2B C3B -174.5(4) . . . . ?
C3B C1B C2B C3B 4.5(7) 2_766 . . . ?
O1B C1B C2B Br1B 4.7(6) . . . . ?
C3B C1B C2B Br1B -176.2(3) 2_766 . . . ?
C1B C2B C3B C1B -4.7(7) . . . 2_766 ?
Br1B C2B C3B C1B 176.1(3) . . . 2_766 ?
C1B C2B C3B Br2B 175.5(3) . . . . ?
Br1B C2B C3B Br2B -3.7(5) . . . . ?
C5 N1 C4 C5 0.4(7) . . . 2_556 ?
N2 N1 C4 C5 -178.4(4) . . . 2_556 ?
C4 N1 C5 C4 -0.4(7) . . . 2_556 ?
N2 N1 C5 C4 178.4(4) . . . 2_556 ?
C10 O2 C8 C9 -167(6) 2_565 . . . ?
C9 O2 C8 C9 2(3) 2_465 . . . ?
C8 O2 C8 C9 -179(2) 2_565 . . . ?
C10 O2 C8 C10 17(8) 2_565 . . . ?
C9 O2 C8 C10 -174(3) 2_465 . . . ?
C8 O2 C8 C10 5(2) 2_565 . . . ?
C9 O2 C8 C10 169(6) 2_465 . . 2_565 ?
C8 O2 C8 C10 -12(5) 2_565 . . 2_565 ?
C10 O2 C8 C8 12(5) 2_565 . . 2_565 ?
C9 O2 C8 C8 -178.8(18) 2_465 . . 2_565 ?
C10 O2 C8 O2 12(5) 2_565 . . 2_565 ?
C9 O2 C8 O2 -178.8(18) 2_465 . . 2_565 ?
C8 O2 C8 O2 0.0000(10) 2_565 . . 2_565 ?
C10 O2 C8 C9 -169(6) 2_565 . . 2_465 ?
C8 O2 C8 C9 178.8(18) 2_565 . . 2_465 ?
O2 C8 C9 O2 -2(3) . . . 2_465 ?
C10 C8 C9 O2 175(2) . . . 2_465 ?
C10 C8 C9 O2 -8(4) 2_565 . . 2_465 ?
C8 C8 C9 O2 -178(5) 2_565 . . 2_465 ?
O2 C8 C9 O2 178.9(19) 2_565 . . 2_465 ?
C9 C8 C9 O2 -1.2(14) 2_465 . . 2_465 ?
O2 C8 C9 C10 -9(5) . . . 1_455 ?
C10 C8 C9 C10 169(5) . . . 1_455 ?
C10 C8 C9 C10 -14(7) 2_565 . . 1_455 ?
C8 C8 C9 C10 175(4) 2_565 . . 1_455 ?
O2 C8 C9 C10 173(3) 2_565 . . 1_455 ?
C9 C8 C9 C10 -7(4) 2_465 . . 1_455 ?
O2 C8 C9 C8 -1.2(15) . . . 2_465 ?
C10 C8 C9 C8 176.0(17) . . . 2_465 ?
C10 C8 C9 C8 -7(3) 2_565 . . 2_465 ?
C8 C8 C9 C8 -177(6) 2_565 . . 2_465 ?
O2 C8 C9 C8 -179.9(14) 2_565 . . 2_465 ?
C9 C8 C9 C8 0.000(3) 2_465 . . 2_465 ?
O2 C8 C10 O2 -13(6) . . . 2_565 ?
C9 C8 C10 O2 170(5) . . . 2_565 ?
C10 C8 C10 O2 -8(4) 2_565 . . 2_565 ?
C8 C8 C10 O2 -8(4) 2_565 . . 2_565 ?
C9 C8 C10 O2 -23(9) 2_465 . . 2_565 ?
O2 C8 C10 C9 -15(6) . . . 1_655 ?
C9 C8 C10 C9 168(5) . . . 1_655 ?
C10 C8 C10 C9 -10(4) 2_565 . . 1_655 ?
C8 C8 C10 C9 -10(4) 2_565 . . 1_655 ?
O2 C8 C10 C9 -2(2) 2_565 . . 1_655 ?
C9 C8 C10 C9 -26(10) 2_465 . . 1_655 ?
O2 C8 C10 C8 -5(2) . . . 2_565 ?
C9 C8 C10 C8 177.9(18) . . . 2_565 ?
C10 C8 C10 C8 -0.002(2) 2_565 . . 2_565 ?
O2 C8 C10 C8 8(4) 2_565 . . 2_565 ?
C9 C8 C10 C8 -15(6) 2_465 . . 2_565 ?

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
_geom_hbond_publ_flag
C4 H4 O1B 0.93 2.42 3.193(5) 140.2 . yes
C7 H2B O1B 0.86 2.22 2.999(5) 149.9 . yes
C7 H7B O1A 0.96 2.15 3.061(6) 158.1 . yes
N2 H2A Br1A 0.86 3.1 3.796(4) 139.3 . yes
N2 H7B O1A 0.96 2.15 3.061(6) 158.1 . yes
N2 H2B O1B 0.86 2.22 2.999(5) 149.9 . yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_systematic        
'N-methylpyridinium tetrabromosemiquinonate acetone solvate'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_refine_special_details          
'N-methyl-4-aminopyridinium cation is disordered about an inversion centre; the structure contains disordered acetone molecules'
####################################################################### 
# 
# 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_pyz_cl4q
_database_code_depnum_ccdc_archive 'CCDC 1921862'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2016-12-07T14:16:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C11 H7 Cl4 N2 O2'
_chemical_formula_sum            'C11 H7 Cl4 N2 O2'
_chemical_formula_weight         340.99

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   7.17000(10)
_cell_length_b                   15.3896(3)
_cell_length_c                   11.7282(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.627(2)
_cell_angle_gamma                90
_cell_volume                     1267.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3620
_cell_measurement_theta_min      2.869
_cell_measurement_theta_max      74.4785
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    8.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.23369
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            5877
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_theta_min         4.8
_diffrn_reflns_theta_max         74.64
_diffrn_reflns_theta_full        74.64
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measured_fraction_theta_full 0.99
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             2570
_reflns_number_gt                2321
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1279
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_number_reflns         2570
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0798P)²+0.0910P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.4
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.42730(8) 0.65788(4) 1.16216(5) 0.0439(2) Uani d . 1 . . Cl
Cl2 0.21875(8) 0.65518(3) 0.89743(4) 0.0407(2) Uani d . 1 . . Cl
Cl3 0.10591(8) 0.31210(3) 0.92384(5) 0.0408(2) Uani d . 1 . . Cl
Cl4 0.30878(9) 0.31407(4) 1.19059(5) 0.0453(2) Uani d . 1 . . Cl
O1 0.4347(3) 0.48768(13) 1.27278(14) 0.0486(4) Uani d . 1 . . O
O2 0.0499(2) 0.48601(11) 0.82381(12) 0.0388(4) Uani d . 1 . . O
C1 0.3484(3) 0.48694(15) 1.16957(17) 0.0327(4) Uani d . 1 . . C
C2 0.3269(3) 0.56389(14) 1.09654(17) 0.0303(4) Uani d . 1 . . C
C3 0.2327(3) 0.56363(13) 0.98333(16) 0.0289(4) Uani d . 1 . . C
C4 0.1446(3) 0.48581(13) 0.92536(16) 0.0289(4) Uani d . 1 . . C
C5 0.1811(3) 0.40741(13) 0.99533(17) 0.0295(4) Uani d . 1 . . C
C6 0.2732(3) 0.40807(14) 1.10923(17) 0.0315(4) Uani d . 1 . . C
N1 -0.1292(3) 0.60010(14) 0.49927(17) 0.0397(4) Uani d . 1 . . N
N2 0.2480(2) 0.61962(12) 0.49083(14) 0.0306(4) Uani d . 1 . . N
C7 -0.0725(3) 0.60977(16) 0.39894(18) 0.0388(5) Uani d . 1 . . C
H7 -0.1639 0.6099 0.3303 0.047 Uiso calc R 1 . . H
C8 0.1163(3) 0.61965(15) 0.39219(17) 0.0354(4) Uani d . 1 . . C
H8 0.1513 0.6262 0.3205 0.043 Uiso calc R 1 . . H
C9 0.1966(3) 0.61073(16) 0.59383(17) 0.0365(5) Uani d . 1 . . C
H9 0.2875 0.6114 0.6627 0.044 Uiso calc R 1 . . H
C10 0.0062(3) 0.60061(16) 0.59588(19) 0.0391(5) Uani d . 1 . . C
H10 -0.0293 0.5939 0.6674 0.047 Uiso calc R 1 . . H
C11 0.4520(3) 0.62806(18) 0.4872(2) 0.0417(5) Uani d . 1 . . C
H11A 0.5263 0.6269 0.565 0.063 Uiso calc R 1 . . H
H11B 0.473 0.682 0.4507 0.063 Uiso calc R 1 . . H
H11C 0.4894 0.5807 0.4434 0.063 Uiso calc R 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.726(2) ?
Cl2 C3 . 1.723(2) ?
Cl3 C5 . 1.721(2) ?
Cl4 C6 . 1.723(2) ?
O1 C1 . 1.244(3) ?
O2 C4 . 1.246(2) ?
C1 C2 . 1.451(3) ?
C1 C6 . 1.453(3) ?
C2 C3 . 1.363(3) ?
C3 C4 . 1.457(3) ?
C4 C5 . 1.453(3) ?
C5 C6 . 1.366(3) ?
N1 C7 . 1.329(3) ?
N1 C10 . 1.335(3) ?
N2 C8 . 1.338(3) ?
N2 C9 . 1.339(3) ?
N2 C11 . 1.478(3) ?
C7 C8 . 1.380(3) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C9 C10 . 1.379(3) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?

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
O1 C1 C2 122.7(2) . . ?
O1 C1 C6 123.0(2) . . ?
C2 C1 C6 114.17(17) . . ?
C3 C2 C1 123.04(18) . . ?
C3 C2 Cl1 121.14(16) . . ?
C1 C2 Cl1 115.82(14) . . ?
C2 C3 C4 122.70(18) . . ?
C2 C3 Cl2 121.75(16) . . ?
C4 C3 Cl2 115.50(14) . . ?
O2 C4 C5 122.91(19) . . ?
O2 C4 C3 123.05(19) . . ?
C5 C4 C3 114.02(17) . . ?
C6 C5 C4 122.88(18) . . ?
C6 C5 Cl3 121.67(16) . . ?
C4 C5 Cl3 115.43(14) . . ?
C5 C6 C1 122.78(18) . . ?
C5 C6 Cl4 121.59(16) . . ?
C1 C6 Cl4 115.63(14) . . ?
C7 N1 C10 116.79(19) . . ?
C8 N2 C9 120.37(19) . . ?
C8 N2 C11 120.34(18) . . ?
C9 N2 C11 119.29(17) . . ?
N1 C7 C8 122.82(19) . . ?
N1 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
N2 C8 C7 118.67(19) . . ?
N2 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N2 C9 C10 118.73(19) . . ?
N2 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
N1 C10 C9 122.6(2) . . ?
N1 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
O1 C1 C2 C3 179.9(2) . . . . ?
C6 C1 C2 C3 4.4(3) . . . . ?
O1 C1 C2 Cl1 -0.5(3) . . . . ?
C6 C1 C2 Cl1 -176.13(14) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
Cl1 C2 C3 C4 -179.36(15) . . . . ?
C1 C2 C3 Cl2 -177.19(15) . . . . ?
Cl1 C2 C3 Cl2 3.3(2) . . . . ?
C2 C3 C4 O2 176.2(2) . . . . ?
Cl2 C3 C4 O2 -6.3(3) . . . . ?
C2 C3 C4 C5 -5.4(3) . . . . ?
Cl2 C3 C4 C5 172.06(14) . . . . ?
O2 C4 C5 C6 -175.2(2) . . . . ?
C3 C4 C5 C6 6.4(3) . . . . ?
O2 C4 C5 Cl3 6.5(3) . . . . ?
C3 C4 C5 Cl3 -171.94(13) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
Cl3 C5 C6 C1 176.14(15) . . . . ?
C4 C5 C6 Cl4 178.34(15) . . . . ?
Cl3 C5 C6 Cl4 -3.5(3) . . . . ?
O1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 -3.4(3) . . . . ?
O1 C1 C6 Cl4 0.7(3) . . . . ?
C2 C1 C6 Cl4 176.21(14) . . . . ?
C10 N1 C7 C8 0.3(4) . . . . ?
C9 N2 C8 C7 -0.4(3) . . . . ?
C11 N2 C8 C7 178.6(2) . . . . ?
N1 C7 C8 N2 -0.1(4) . . . . ?
C8 N2 C9 C10 0.8(3) . . . . ?
C11 N2 C9 C10 -178.3(2) . . . . ?
C7 N1 C10 C9 0.1(4) . . . . ?
N2 C9 C10 N1 -0.6(4) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_cl4q_3ampy
_database_code_depnum_ccdc_archive 'CCDC 1921859'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2017-01-16T14:12:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H9 Cl4 N2 O2'
_chemical_formula_sum            'C12 H9 Cl4 N2 O2'
_chemical_formula_weight         355.01

#==============================================================================

# CRYSTAL DATA

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

_cell_length_a                   7.1294(4)
_cell_length_b                   9.5042(8)
_cell_length_c                   11.0035(9)
_cell_angle_alpha                106.258(7)
_cell_angle_beta                 91.624(6)
_cell_angle_gamma                106.085(6)
_cell_volume                     683.20(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2451
_cell_measurement_theta_min      4.2096
_cell_measurement_theta_max      75.8428
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             358
_exptl_absorpt_coefficient_mu    7.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.56883
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            5564
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_theta_min         4.21
_diffrn_reflns_theta_max         76.03
_diffrn_reflns_theta_full        76.03
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             2779
_reflns_number_gt                2491
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1619
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         2779
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0718P)²+1.1030P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.30938(15) 0.92227(11) 0.66868(8) 0.0487(3) Uani d . 1 . . Cl
Cl2 0.24262(16) 0.64928(10) 0.41638(9) 0.0509(3) Uani d . 1 . . Cl
Cl3 0.12360(16) 1.01287(12) 0.14428(9) 0.0521(3) Uani d . 1 . . Cl
Cl4 0.19191(17) 1.28527(10) 0.39735(10) 0.0534(3) Uani d . 1 . . Cl
O1 0.2296(4) 1.1923(3) 0.6279(3) 0.0482(6) Uani d . 1 . . O
O2 0.1227(4) 0.7228(3) 0.1907(2) 0.0480(6) Uani d . 1 . . O
C1 0.2138(5) 1.0875(4) 0.5267(3) 0.0377(7) Uani d . 1 . . C
C2 0.2357(5) 0.9392(4) 0.5239(3) 0.0376(7) Uani d . 1 . . C
C3 0.2079(5) 0.8212(4) 0.4143(3) 0.0373(7) Uani d . 1 . . C
C4 0.1539(5) 0.8325(4) 0.2906(3) 0.0384(7) Uani d . 1 . . C
C5 0.1530(5) 0.9854(4) 0.2915(3) 0.0387(7) Uani d . 1 . . C
C6 0.1812(5) 1.1029(4) 0.4006(3) 0.0387(7) Uani d . 1 . . C
N1 -0.6154(5) 0.6219(4) -0.1681(3) 0.0459(7) Uani d . 1 . . N
N2 -0.1675(6) 0.5802(5) -0.0412(4) 0.0679(11) Uani d . 1 . . N
H2A -0.1524 0.5069 -0.1029 0.081 Uiso calc R 1 . . H
H2B -0.0833 0.6201 0.0258 0.081 Uiso calc R 1 . . H
C7 -0.4615(6) 0.5692(4) -0.1576(3) 0.0458(8) Uani d . 1 . . C
H7 -0.4462 0.4886 -0.2236 0.055 Uiso calc R 1 . . H
C8 -0.3238(6) 0.6329(4) -0.0494(4) 0.0443(8) Uani d . 1 . . C
C9 -0.3576(7) 0.7503(5) 0.0485(4) 0.0508(9) Uani d . 1 . . C
H9 -0.2733 0.7926 0.1241 0.061 Uiso calc R 1 . . H
C10 -0.5128(6) 0.8027(5) 0.0338(4) 0.0535(10) Uani d . 1 . . C
H10 -0.5321 0.8824 0.0989 0.064 Uiso calc R 1 . . H
C11 -0.6423(7) 0.7398(5) -0.0760(4) 0.0536(10) Uani d . 1 . . C
H11 -0.7464 0.7781 -0.0864 0.064 Uiso calc R 1 . . H
C12 -0.7587(8) 0.5482(5) -0.2832(4) 0.0648(13) Uani d . 1 . . C
H12A -0.8597 0.598 -0.2772 0.097 Uiso calc R 1 . . H
H12B -0.8164 0.4417 -0.2904 0.097 Uiso calc R 1 . . H
H12C -0.6932 0.5568 -0.357 0.097 Uiso calc R 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.726(4) ?
Cl2 C3 . 1.725(3) ?
Cl3 C5 . 1.727(3) ?
Cl4 C6 . 1.725(3) ?
O1 C1 . 1.247(4) ?
O2 C4 . 1.249(4) ?
C1 C2 . 1.453(5) ?
C1 C6 . 1.454(5) ?
C2 C3 . 1.363(5) ?
C3 C4 . 1.445(5) ?
C4 C5 . 1.452(5) ?
C5 C6 . 1.356(5) ?
N1 C7 . 1.341(5) ?
N1 C11 . 1.347(5) ?
N1 C12 . 1.474(5) ?
N2 C8 . 1.352(5) ?
N2 H2A . 0.86 ?
N2 H2B . 0.86 ?
C7 C8 . 1.396(6) ?
C7 H7 . 0.93 ?
C8 C9 . 1.398(5) ?
C9 C10 . 1.356(6) ?
C9 H9 . 0.93 ?
C10 C11 . 1.377(6) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?

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
O1 C1 C2 122.6(3) . . ?
O1 C1 C6 124.0(3) . . ?
C2 C1 C6 113.4(3) . . ?
C3 C2 C1 122.9(3) . . ?
C3 C2 Cl1 121.2(3) . . ?
C1 C2 Cl1 115.8(2) . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 Cl2 120.9(3) . . ?
C4 C3 Cl2 116.1(2) . . ?
O2 C4 C3 122.9(3) . . ?
O2 C4 C5 123.0(3) . . ?
C3 C4 C5 114.0(3) . . ?
C6 C5 C4 122.6(3) . . ?
C6 C5 Cl3 121.1(3) . . ?
C4 C5 Cl3 116.2(3) . . ?
C5 C6 C1 123.4(3) . . ?
C5 C6 Cl4 121.2(3) . . ?
C1 C6 Cl4 115.3(3) . . ?
C7 N1 C11 121.6(3) . . ?
C7 N1 C12 119.0(3) . . ?
C11 N1 C12 119.4(4) . . ?
C8 N2 H2A 120 . . ?
C8 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
N1 C7 C8 121.2(3) . . ?
N1 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
N2 C8 C7 120.5(4) . . ?
N2 C8 C9 122.6(4) . . ?
C7 C8 C9 116.9(4) . . ?
C10 C9 C8 120.3(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.0(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
N1 C11 C10 118.8(4) . . ?
N1 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
O1 C1 C2 C3 176.2(4) . . . . ?
C6 C1 C2 C3 -6.4(5) . . . . ?
O1 C1 C2 Cl1 -6.2(5) . . . . ?
C6 C1 C2 Cl1 171.1(3) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
Cl1 C2 C3 C4 -177.4(3) . . . . ?
C1 C2 C3 Cl2 178.2(3) . . . . ?
Cl1 C2 C3 Cl2 0.8(5) . . . . ?
C2 C3 C4 O2 -177.8(4) . . . . ?
Cl2 C3 C4 O2 4.0(5) . . . . ?
C2 C3 C4 C5 6.4(5) . . . . ?
Cl2 C3 C4 C5 -171.9(3) . . . . ?
O2 C4 C5 C6 177.9(4) . . . . ?
C3 C4 C5 C6 -6.2(5) . . . . ?
O2 C4 C5 Cl3 -4.6(5) . . . . ?
C3 C4 C5 Cl3 171.3(3) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
Cl3 C5 C6 C1 -177.7(3) . . . . ?
C4 C5 C6 Cl4 176.6(3) . . . . ?
Cl3 C5 C6 Cl4 -0.8(5) . . . . ?
O1 C1 C6 C5 -176.1(4) . . . . ?
C2 C1 C6 C5 6.6(5) . . . . ?
O1 C1 C6 Cl4 6.9(5) . . . . ?
C2 C1 C6 Cl4 -170.4(3) . . . . ?
C11 N1 C7 C8 1.1(6) . . . . ?
C12 N1 C7 C8 -178.7(4) . . . . ?
N1 C7 C8 N2 -178.9(4) . . . . ?
N1 C7 C8 C9 2.0(6) . . . . ?
N2 C8 C9 C10 177.7(4) . . . . ?
C7 C8 C9 C10 -3.2(6) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C7 N1 C11 C10 -2.9(6) . . . . ?
C12 N1 C11 C10 176.8(4) . . . . ?
C9 C10 C11 N1 1.7(7) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_s135
_database_code_depnum_ccdc_archive 'CCDC 1921858'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2018-12-07T15:01:23-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C12 H9 Cl4 N2 O2'
_chemical_formula_moiety         'C6 Cl4 O2, C6 H9 N2'
_chemical_formula_weight         355.01

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_Hall  '-I 2ya'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,y,-z
3 -x,-y,-z
4 1/2+x,-y,z
5 1/2+x,1/2+y,1/2+z
6 -x,1/2+y,1/2-z
7 1/2-x,1/2-y,1/2-z
8 x,1/2-y,1/2+z

_cell_length_a                   18.7356(12)
_cell_length_b                   7.1485(8)
_cell_length_c                   21.1647(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.602(8)
_cell_angle_gamma                90
_cell_volume                     2766.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1924
_cell_measurement_theta_min      4.271
_cell_measurement_theta_max      76.095
_cell_measurement_temperature    293(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    7.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.49091
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6397
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_theta_min         4.281
_diffrn_reflns_theta_max         76.813
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2836
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.2296
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_number_reflns         2836
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1175P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.38722(5) 0.4188(2) 0.20300(6) 0.0726(4) Uani d 1 . . Cl
Cl2 0.26157(7) 0.4987(2) 0.08014(6) 0.0684(4) Uani d 1 . . Cl
Cl3 0.06943(6) 0.5638(2) 0.23450(7) 0.0798(5) Uani d 1 . . Cl
Cl4 0.19580(7) 0.4938(2) 0.35615(5) 0.0695(4) Uani d 1 . . Cl
O1 0.33356(14) 0.3885(5) 0.32206(14) 0.0579(8) Uani d 1 . . O
O2 0.11954(17) 0.5533(5) 0.11254(16) 0.0625(8) Uani d 1 . . O
C1 0.28453(19) 0.4330(6) 0.2741(2) 0.0487(9) Uani d 1 . . C
C2 0.2982(2) 0.4445(6) 0.2093(2) 0.0502(9) Uani d 1 . . C
C3 0.2438(2) 0.4841(6) 0.1564(2) 0.0489(9) Uani d 1 . . C
C4 0.1690(2) 0.5160(6) 0.1612(2) 0.0510(9) Uani d 1 . . C
C5 0.1566(2) 0.5147(6) 0.2261(2) 0.0525(10) Uani d 1 . . C
C6 0.2114(2) 0.4771(6) 0.2790(2) 0.0496(9) Uani d 1 . . C
N1 0.0483(2) 0.6045(7) 0.4259(2) 0.0692(11) Uani d 1 . . N
N2 -0.0416(2) 0.3982(7) 0.3789(2) 0.0752(12) Uani d 1 . . N
H2A -0.063288 0.484074 0.353313 0.09 Uiso calc 1 . . H
H2B -0.059634 0.287139 0.3768 0.09 Uiso calc 1 . . H
C7 0.0193(2) 0.4367(7) 0.4214(2) 0.0584(10) Uani d 1 . . C
C8 0.0549(3) 0.2963(13) 0.4627(3) 0.098(2) Uani d 1 . . C
H8 0.036491 0.175053 0.458536 0.117 Uiso calc 1 . . H
C9 0.1153(5) 0.334(2) 0.5083(4) 0.139(5) Uani d 1 . . C
H9 0.137695 0.244073 0.537817 0.167 Uiso calc 1 . . H
C10 0.1418(4) 0.511(2) 0.5090(4) 0.153(6) Uani d 1 . . C
H10 0.185194 0.538294 0.538301 0.183 Uiso calc 1 . . H
C11 0.1099(3) 0.6460(14) 0.4707(3) 0.104(3) Uani d 1 . . C
H11 0.12904 0.766486 0.474283 0.124 Uiso calc 1 . . H
C12 0.0146(4) 0.7449(10) 0.3814(4) 0.096(2) Uani d 1 . . C
H12C 0.04151 0.859736 0.390311 0.144 Uiso calc 1 . . H
H12B 0.014455 0.705292 0.33798 0.144 Uiso calc 1 . . H
H12A -0.034752 0.764175 0.38578 0.144 Uiso calc 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.712(4) ?
Cl2 C3 . 1.721(4) ?
Cl3 C5 . 1.717(4) ?
Cl4 C6 . 1.725(4) ?
O1 C1 . 1.253(5) ?
O2 C4 . 1.254(5) ?
C1 C6 . 1.431(5) ?
C1 C2 . 1.450(6) ?
C2 C3 . 1.369(6) ?
C3 C4 . 1.446(6) ?
C4 C5 . 1.442(6) ?
C5 C6 . 1.371(6) ?
N1 C7 . 1.312(7) ?
N1 C11 . 1.356(7) ?
N1 C12 . 1.427(8) ?
N2 C7 . 1.319(6) ?
N2 H2A . 0.86 ?
N2 H2B . 0.86 ?
C7 C8 . 1.401(9) ?
C8 C9 . 1.345(12) ?
C8 H8 . 0.93 ?
C9 C10 . 1.356(17) ?
C9 H9 . 0.93 ?
C10 C11 . 1.318(16) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12C . 0.96 ?
C12 H12B . 0.96 ?
C12 H12A . 0.96 ?

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
O1 C1 C6 122.7(4) . . ?
O1 C1 C2 122.1(3) . . ?
C6 C1 C2 115.2(3) . . ?
C3 C2 C1 122.1(4) . . ?
C3 C2 Cl1 121.5(3) . . ?
C1 C2 Cl1 116.3(3) . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 Cl2 121.2(3) . . ?
C4 C3 Cl2 116.4(3) . . ?
O2 C4 C5 122.7(4) . . ?
O2 C4 C3 122.0(4) . . ?
C5 C4 C3 115.2(4) . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 Cl3 121.1(4) . . ?
C4 C5 Cl3 116.8(3) . . ?
C5 C6 C1 122.9(4) . . ?
C5 C6 Cl4 120.5(3) . . ?
C1 C6 Cl4 116.6(3) . . ?
C7 N1 C11 121.8(6) . . ?
C7 N1 C12 118.6(5) . . ?
C11 N1 C12 119.6(7) . . ?
C7 N2 H2A 120 . . ?
C7 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
N1 C7 N2 121.6(5) . . ?
N1 C7 C8 118.4(5) . . ?
N2 C7 C8 120.0(6) . . ?
C9 C8 C7 121.0(9) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 116.3(9) . . ?
C8 C9 H9 121.9 . . ?
C10 C9 H9 121.9 . . ?
C11 C10 C9 124.1(8) . . ?
C11 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C10 C11 N1 118.2(9) . . ?
C10 C11 H11 120.9 . . ?
N1 C11 H11 120.9 . . ?
N1 C12 H12C 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
N1 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?

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
O1 C1 C2 C3 176.7(4) . . . . ?
C6 C1 C2 C3 -3.7(6) . . . . ?
O1 C1 C2 Cl1 -6.8(6) . . . . ?
C6 C1 C2 Cl1 172.8(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
Cl1 C2 C3 C4 -176.7(3) . . . . ?
C1 C2 C3 Cl2 179.5(3) . . . . ?
Cl1 C2 C3 Cl2 3.2(5) . . . . ?
C2 C3 C4 O2 179.6(4) . . . . ?
Cl2 C3 C4 O2 -0.4(6) . . . . ?
C2 C3 C4 C5 3.7(6) . . . . ?
Cl2 C3 C4 C5 -176.2(3) . . . . ?
O2 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C5 C6 -3.0(6) . . . . ?
O2 C4 C5 Cl3 1.0(6) . . . . ?
C3 C4 C5 Cl3 176.8(3) . . . . ?
C4 C5 C6 C1 -1.2(7) . . . . ?
Cl3 C5 C6 C1 179.1(3) . . . . ?
C4 C5 C6 Cl4 175.3(3) . . . . ?
Cl3 C5 C6 Cl4 -4.5(6) . . . . ?
O1 C1 C6 C5 -175.9(4) . . . . ?
C2 C1 C6 C5 4.4(6) . . . . ?
O1 C1 C6 Cl4 7.5(6) . . . . ?
C2 C1 C6 Cl4 -172.1(3) . . . . ?
C11 N1 C7 N2 178.2(5) . . . . ?
C12 N1 C7 N2 -3.2(7) . . . . ?
C11 N1 C7 C8 -2.3(7) . . . . ?
C12 N1 C7 C8 176.3(5) . . . . ?
N1 C7 C8 C9 3.4(8) . . . . ?
N2 C7 C8 C9 -177.0(6) . . . . ?
C7 C8 C9 C10 -4.1(12) . . . . ?
C8 C9 C10 C11 3.9(15) . . . . ?
C9 C10 C11 N1 -2.9(14) . . . . ?
C7 N1 C11 C10 2.0(9) . . . . ?
C12 N1 C11 C10 -176.6(7) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_cl4q_4ampy
_database_code_depnum_ccdc_archive 'CCDC 1921860'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2017-02-08T11:43:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H9 Cl6 N2 O3'
_chemical_formula_sum            'C15 H9 Cl6 Cu0 N2 O3'
_chemical_formula_weight         477.94

#==============================================================================

# CRYSTAL DATA

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

_cell_length_a                   9.6014(5)
_cell_length_b                   10.0218(6)
_cell_length_c                   10.7402(6)
_cell_angle_alpha                66.219(5)
_cell_angle_beta                 72.013(5)
_cell_angle_gamma                89.522(5)
_cell_volume                     891.44(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4819
_cell_measurement_theta_min      4.7692
_cell_measurement_theta_max      75.7258
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    8.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.65319
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            7801
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_theta_min         4.77
_diffrn_reflns_theta_max         75.91
_diffrn_reflns_theta_full        75.91
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.,N-methyl-4aminopyridinium cation is disordered about an inversion centre
;
_reflns_number_total             3662
_reflns_number_gt                3367
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.177
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_number_reflns         3662
_refine_ls_number_parameters     241
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1029P)²+0.7143P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.62533(10) 0.22167(9) 0.71577(8) 0.0494(2) Uani d . 1 . . Cl
Cl2 0.90837(8) 0.40072(9) 0.44203(9) 0.0514(2) Uani d . 1 . . Cl
Cl3 0.56776(10) 0.54946(9) 0.10422(8) 0.0524(3) Uani d . 1 . . Cl
Cl4 0.28444(8) 0.37288(9) 0.37968(10) 0.0509(2) Uani d . 1 . . Cl
O1 0.3625(3) 0.2190(3) 0.6379(3) 0.0593(6) Uani d . 1 . . O
O2 0.8352(3) 0.5353(3) 0.1783(3) 0.0567(6) Uani d . 1 . . O
C1 0.4694(3) 0.2927(3) 0.5337(3) 0.0375(6) Uani d . 1 . . C
C2 0.6176(3) 0.3066(3) 0.5444(3) 0.0357(5) Uani d . 1 . . C
C3 0.7371(3) 0.3827(3) 0.4291(3) 0.0355(5) Uani d . 1 . . C
C4 0.7275(3) 0.4612(3) 0.2832(3) 0.0378(6) Uani d . 1 . . C
C5 0.5793(3) 0.4530(3) 0.2726(3) 0.0360(6) Uani d . 1 . . C
C6 0.4592(3) 0.3764(3) 0.3887(3) 0.0360(6) Uani d . 1 . . C
Cl5 0.18982(7) -0.02746(8) 0.47005(8) 0.0404(2) Uani d . 1 . . Cl
Cl6 0.45974(8) 0.17181(8) 0.20078(7) 0.0403(2) Uani d . 1 . . Cl
O3 0.2721(2) -0.1912(2) 0.7276(2) 0.0392(4) Uani d . 1 . . O
C7 0.3764(3) -0.1000(3) 0.6231(3) 0.0300(5) Uani d . 1 . . C
C8 0.3624(3) -0.0133(3) 0.4835(3) 0.0307(5) Uani d . 1 . . C
C9 0.4786(3) 0.0790(3) 0.3676(3) 0.0301(5) Uani d . 1 . . C
N1 -0.1383(3) 0.1739(3) 0.9122(3) 0.0483(6) Uani d P 0.5 . . N
N2 -0.0619(6) -0.2102(5) 0.8571(6) 0.103(2) Uani d P 0.5 . . N
H2A -0.117 -0.2915 0.919 0.124 Uiso calc PR 0.5 . . H
H2B 0.0109 -0.2091 0.7856 0.124 Uiso calc PR 0.5 . . H
C10 -0.0215(3) 0.1724(4) 0.7998(3) 0.0475(7) Uani d D 1 . . C
H10 0.0421 0.2588 0.7358 0.057 Uiso calc R 1 . . H
C11 0.0023(4) 0.0488(4) 0.7809(3) 0.0528(8) Uani d . 1 . . C
H11 0.0829 0.0514 0.7044 0.063 Uiso calc R 1 . . H
C12 -0.0899(3) -0.0826(3) 0.8723(3) 0.0491(7) Uani d P 0.5 . . C
C14 -0.2293(4) 0.0430(4) 1.0048(4) 0.0531(8) Uani d D 1 . . C
H14 -0.3088 0.0406 1.082 0.064 Uiso calc R 1 . . H
C13 -0.2061(3) -0.0817(4) 0.9862(3) 0.0497(7) Uani d . 1 . . C
H13 -0.2692 -0.1682 1.0511 0.06 Uiso calc R 1 . . H
C15 -0.1614(6) 0.3010(6) 0.9335(6) 0.113(2) Uani d P 0.5 . . C
H15A -0.0875 0.3803 0.8589 0.17 Uiso calc PR 0.5 . . H
H15B -0.1551 0.2852 1.0258 0.17 Uiso calc PR 0.5 . . H
H15C -0.2575 0.3255 0.9306 0.17 Uiso calc PR 0.5 . . H
C15B -0.0619(6) -0.2102(5) 0.8571(6) 0.103(2) Uani d P 0.5 . . C
H15D 0.0355 -0.1961 0.7895 0.155 Uiso calc PR 0.5 . . H
H15E -0.1332 -0.2367 0.8222 0.155 Uiso calc PR 0.5 . . H
H15F -0.0683 -0.2873 0.9488 0.155 Uiso calc PR 0.5 . . H
C12B -0.1383(3) 0.1739(3) 0.9122(3) 0.0483(6) Uani d PD 0.5 . . C
N2B -0.1614(6) 0.3010(6) 0.9335(6) 0.113(2) Uani d PD 0.5 . . N
N1B -0.0899(3) -0.0826(3) 0.8723(3) 0.0491(7) Uani d P 0.5 . . N
H2C -0.246(3) 0.301(4) 0.986(5) 0.059 Uiso d PD 0.5 . . H
H2D -0.086(3) 0.362(5) 0.898(6) 0.059 Uiso d PD 0.5 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . 1.714(3) ?
Cl2 C3 . 1.710(3) ?
Cl3 C5 . 1.711(3) ?
Cl4 C6 . 1.712(3) ?
O1 C1 . 1.220(4) ?
O2 C4 . 1.228(3) ?
C1 C2 . 1.475(4) ?
C1 C6 . 1.476(4) ?
C2 C3 . 1.344(4) ?
C3 C4 . 1.476(4) ?
C4 C5 . 1.468(4) ?
C5 C6 . 1.352(4) ?
Cl5 C8 . 1.719(3) ?
Cl6 C9 . 1.721(3) ?
O3 C7 . 1.261(3) ?
C7 C8 . 1.446(4) ?
C7 C9 2_656 1.449(4) ?
C8 C9 . 1.371(4) ?
C9 C7 2_656 1.449(4) ?
N1 C10 . 1.375(4) ?
N1 C14 . 1.380(4) ?
N1 C15 . 1.387(5) ?
N2 C12 . 1.367(5) ?
N2 H2A . 0.86 ?
N2 H2B . 0.86 ?
C10 C11 . 1.341(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.386(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.382(4) ?
C14 C13 . 1.348(5) ?
C14 H14 . 0.93 ?
C13 H13 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C15 H2C . 0.837(19) ?
C15 H2D . 0.836(19) ?

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
O1 C1 C2 122.3(3) . . ?
O1 C1 C6 122.5(3) . . ?
C2 C1 C6 115.2(2) . . ?
C3 C2 C1 122.6(2) . . ?
C3 C2 Cl1 122.5(2) . . ?
C1 C2 Cl1 114.9(2) . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 Cl2 122.6(2) . . ?
C4 C3 Cl2 115.5(2) . . ?
O2 C4 C5 121.8(3) . . ?
O2 C4 C3 122.2(3) . . ?
C5 C4 C3 115.8(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 Cl3 122.2(2) . . ?
C4 C5 Cl3 115.6(2) . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 Cl4 122.7(2) . . ?
C1 C6 Cl4 115.1(2) . . ?
O3 C7 C8 122.7(2) . . ?
O3 C7 C9 122.3(2) . 2_656 ?
C8 C7 C9 114.9(2) . 2_656 ?
C9 C8 C7 122.5(2) . . ?
C9 C8 Cl5 120.9(2) . . ?
C7 C8 Cl5 116.56(19) . . ?
C8 C9 C7 122.5(2) . 2_656 ?
C8 C9 Cl6 120.9(2) . . ?
C7 C9 Cl6 116.55(18) 2_656 . ?
C10 N1 C14 117.3(3) . . ?
C10 N1 C15 121.3(3) . . ?
C14 N1 C15 121.4(3) . . ?
C12 N2 H2A 120 . . ?
C12 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
C11 C10 N1 121.3(3) . . ?
C11 C10 H10 119.4 . . ?
N1 C10 H10 119.4 . . ?
C10 C11 C12 121.8(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
N2 C12 C13 121.0(3) . . ?
N2 C12 C11 121.8(3) . . ?
C13 C12 C11 117.0(3) . . ?
C13 C14 N1 121.7(3) . . ?
C13 C14 H14 119.1 . . ?
N1 C14 H14 119.1 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C15 H2C 115(2) . . ?
H15A C15 H2C 131.3 . . ?
H15B C15 H2C 73 . . ?
H15C C15 H2C 37.5 . . ?
N1 C15 H2D 115(3) . . ?
H15A C15 H2D 24 . . ?
H15B C15 H2D 86.1 . . ?
H15C C15 H2D 124.5 . . ?
H2C C15 H2D 130(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
O1 C1 C2 C3 177.3(3) . . . . ?
C6 C1 C2 C3 -3.8(4) . . . . ?
O1 C1 C2 Cl1 -4.1(4) . . . . ?
C6 C1 C2 Cl1 174.79(19) . . . . ?
C1 C2 C3 C4 1.5(4) . . . . ?
Cl1 C2 C3 C4 -177.1(2) . . . . ?
C1 C2 C3 Cl2 179.2(2) . . . . ?
Cl1 C2 C3 Cl2 0.6(4) . . . . ?
C2 C3 C4 O2 177.3(3) . . . . ?
Cl2 C3 C4 O2 -0.5(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
Cl2 C3 C4 C5 -176.74(19) . . . . ?
O2 C4 C5 C6 -177.4(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
O2 C4 C5 Cl3 1.6(4) . . . . ?
C3 C4 C5 Cl3 177.81(19) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
Cl3 C5 C6 C1 179.7(2) . . . . ?
C4 C5 C6 Cl4 176.8(2) . . . . ?
Cl3 C5 C6 Cl4 -2.0(4) . . . . ?
O1 C1 C6 C5 -177.3(3) . . . . ?
C2 C1 C6 C5 3.8(4) . . . . ?
O1 C1 C6 Cl4 4.3(4) . . . . ?
C2 C1 C6 Cl4 -174.59(19) . . . . ?
O3 C7 C8 C9 -175.9(2) . . . . ?
C9 C7 C8 C9 1.6(4) 2_656 . . . ?
O3 C7 C8 Cl5 5.8(3) . . . . ?
C9 C7 C8 Cl5 -176.74(17) 2_656 . . . ?
C7 C8 C9 C7 -1.7(4) . . . 2_656 ?
Cl5 C8 C9 C7 176.55(18) . . . 2_656 ?
C7 C8 C9 Cl6 176.10(18) . . . . ?
Cl5 C8 C9 Cl6 -5.6(3) . . . . ?
C14 N1 C10 C11 0.3(5) . . . . ?
C15 N1 C10 C11 178.7(5) . . . . ?
N1 C10 C11 C12 0.6(5) . . . . ?
C10 C11 C12 N2 -177.0(4) . . . . ?
C10 C11 C12 C13 -1.4(5) . . . . ?
C10 N1 C14 C13 -0.4(5) . . . . ?
C15 N1 C14 C13 -178.8(5) . . . . ?
N1 C14 C13 C12 -0.5(6) . . . . ?
N2 C12 C13 C14 176.9(5) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_nikcl4q-2
_database_code_depnum_ccdc_archive 'CCDC 1921861'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2016-09-07T10:47:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H8 Cl4 N1 O3'
_chemical_formula_sum            'C31 H20 Cl10 N2 O9'
_chemical_formula_weight         918.99

#==============================================================================

# CRYSTAL DATA

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

_cell_length_a                   9.5672(5)
_cell_length_b                   10.4858(6)
_cell_length_c                   18.7361(9)
_cell_angle_alpha                82.100(4)
_cell_angle_beta                 77.722(4)
_cell_angle_gamma                72.784(5)
_cell_volume                     1748.72(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6451
_cell_measurement_theta_min      4.4249
_cell_measurement_theta_max      75.8158
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    7.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.53994
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            16558
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_unetI/netI     0.05
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         76
_diffrn_reflns_theta_full        76
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             7177
_reflns_number_gt                5779
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.1969
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         7177
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1191P)²+0.4806P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.11
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1A 1.17772(10) 0.67378(10) 0.27398(6) 0.0573(3) Uani d . 1 . . Cl
Cl2A 0.96789(9) 0.88508(8) 0.17850(5) 0.0469(2) Uani d . 1 . . Cl
Cl3A 0.55776(9) 0.60916(9) 0.25883(5) 0.0487(2) Uani d . 1 . . Cl
Cl4A 0.76717(11) 0.39962(9) 0.35346(5) 0.0549(2) Uani d . 1 . . Cl
O1A 1.0590(3) 0.4480(3) 0.33883(15) 0.0520(6) Uani d . 1 . . O
O2A 0.6926(3) 0.8167(2) 0.17741(14) 0.0436(5) Uani d . 1 . . O
C1A 0.9734(4) 0.5346(3) 0.30301(18) 0.0399(7) Uani d . 1 . . C
C2A 1.0114(3) 0.6525(3) 0.26425(18) 0.0391(6) Uani d . 1 . . C
C3A 0.9197(3) 0.7445(3) 0.22237(18) 0.0370(6) Uani d . 1 . . C
C4A 0.7755(3) 0.7336(3) 0.21535(17) 0.0360(6) Uani d . 1 . . C
C5A 0.7339(3) 0.6199(3) 0.25893(18) 0.0383(6) Uani d . 1 . . C
C6A 0.8250(4) 0.5282(3) 0.30002(18) 0.0393(6) Uani d . 1 . . C
Cl1B 1.18696(8) 0.64010(9) 0.06905(5) 0.0457(2) Uani d . 1 . . Cl
Cl2B 0.96365(9) 0.86391(8) -0.01557(5) 0.0460(2) Uani d . 1 . . Cl
Cl3B 0.55838(9) 0.58402(9) 0.06336(5) 0.0475(2) Uani d . 1 . . Cl
Cl4B 0.78148(10) 0.36388(8) 0.15010(5) 0.0477(2) Uani d . 1 . . Cl
O1B 1.0532(3) 0.4347(2) 0.15029(16) 0.0506(6) Uani d . 1 . . O
O2B 0.6813(3) 0.8039(3) -0.00679(15) 0.0481(6) Uani d . 1 . . O
C1B 0.9694(3) 0.5182(3) 0.11299(18) 0.0370(6) Uani d . 1 . . C
C2B 1.0091(3) 0.6332(3) 0.07094(17) 0.0345(6) Uani d . 1 . . C
C3B 0.9142(3) 0.7269(3) 0.03257(16) 0.0345(6) Uani d . 1 . . C
C4B 0.7667(3) 0.7184(3) 0.02930(17) 0.0349(6) Uani d . 1 . . C
C5B 0.7294(3) 0.6009(3) 0.06893(17) 0.0359(6) Uani d . 1 . . C
C6B 0.8245(3) 0.5069(3) 0.10720(17) 0.0351(6) Uani d . 1 . . C
Cl1C 0.33223(12) 0.50075(13) 0.44227(7) 0.0677(3) Uani d . 1 . . Cl
Cl2C -0.08270(14) 0.22913(10) 0.51605(6) 0.0647(3) Uani d . 1 . . Cl
O1C 0.2083(4) 0.2741(3) 0.4692(2) 0.0750(9) Uani d . 1 . . O
C1C 0.1137(5) 0.3772(4) 0.4814(2) 0.0523(8) Uani d . 1 . . C
C2C 0.1501(4) 0.5068(4) 0.4736(2) 0.0509(8) Uani d . 1 . . C
C3C -0.0448(5) 0.3795(4) 0.5084(2) 0.0500(8) Uani d . 1 . . C
O3A 1.2562(5) -0.0235(4) 0.44624(18) 0.0777(10) Uani d . 1 . . O
O4A 1.4610(4) -0.1339(4) 0.37272(18) 0.0809(11) Uani d . 1 . . O
N1A 1.2826(3) -0.0006(3) 0.19113(15) 0.0399(6) Uani d . 1 . . N
C7A 1.3367(4) -0.0501(3) 0.25246(19) 0.0422(7) Uani d . 1 . . C
H7A 1.4192 -0.1245 0.2514 0.051 Uiso calc R 1 . . H
C8A 1.2705(4) 0.0087(3) 0.3172(2) 0.0462(7) Uani d . 1 . . C
C9A 1.1485(5) 0.1207(4) 0.3171(2) 0.0543(9) Uani d . 1 . . C
H9A 1.1016 0.1607 0.3605 0.065 Uiso calc R 1 . . H
C10A 1.0975(5) 0.1718(4) 0.2539(3) 0.0591(10) Uani d . 1 . . C
H10A 1.017 0.2477 0.2535 0.071 Uiso calc R 1 . . H
C11A 1.1665(4) 0.1100(4) 0.1905(2) 0.0492(8) Uani d . 1 . . C
H11A 1.1328 0.1447 0.1469 0.059 Uiso calc R 1 . . H
C12A 1.3490(4) -0.0703(4) 0.1232(2) 0.0497(8) Uani d . 1 . . C
H12A 1.2985 -0.0229 0.0843 0.075 Uiso calc R 1 . . H
H12B 1.3392 -0.1599 0.1313 0.075 Uiso calc R 1 . . H
H12C 1.4525 -0.0734 0.1101 0.075 Uiso calc R 1 . . H
C13A 1.3272(5) -0.0491(4) 0.3865(2) 0.0577(9) Uani d . 1 . . C
C14A 1.5201(8) -0.2054(7) 0.4364(3) 0.104(2) Uani d . 1 . . C
H14C 1.617 -0.2643 0.4211 0.156 Uiso calc R 1 . . H
H14A 1.455 -0.2568 0.4633 0.156 Uiso calc R 1 . . H
H14B 1.5272 -0.1424 0.4672 0.156 Uiso calc R 1 . . H
O3B 1.5579(5) 0.1740(5) 0.3911(2) 0.1055(17) Uani d . 1 . . O
O4B 1.7454(4) 0.0466(4) 0.31752(17) 0.0740(10) Uani d . 1 . . O
N1B 1.5524(3) 0.1810(3) 0.13954(15) 0.0384(5) Uani d . 1 . . N
C7B 1.6117(4) 0.1320(3) 0.19975(19) 0.0401(6) Uani d . 1 . . C
H7B 1.6959 0.0591 0.1973 0.048 Uiso calc R 1 . . H
C8B 1.5484(4) 0.1891(4) 0.2653(2) 0.0438(7) Uani d . 1 . . C
C9B 1.4214(4) 0.2974(4) 0.2678(2) 0.0548(9) Uani d . 1 . . C
H9B 1.377 0.3374 0.3114 0.066 Uiso calc R 1 . . H
C10B 1.3628(4) 0.3442(4) 0.2061(3) 0.0572(9) Uani d . 1 . . C
H10B 1.2773 0.4157 0.2074 0.069 Uiso calc R 1 . . H
C11B 1.4308(4) 0.2852(4) 0.1415(2) 0.0478(8) Uani d . 1 . . C
H11B 1.3919 0.318 0.099 0.057 Uiso calc R 1 . . H
C12B 1.6281(4) 0.1210(4) 0.0697(2) 0.0504(8) Uani d . 1 . . C
H12D 1.5738 0.1657 0.0316 0.076 Uiso calc R 1 . . H
H12F 1.6323 0.0276 0.0748 0.076 Uiso calc R 1 . . H
H12E 1.7273 0.1306 0.0573 0.076 Uiso calc R 1 . . H
C13B 1.6153(5) 0.1354(4) 0.3319(2) 0.0548(9) Uani d . 1 . . C
C14B 1.8209(7) -0.0111(7) 0.3781(3) 0.0872(18) Uani d . 1 . . C
H14F 1.9142 -0.0736 0.3607 0.131 Uiso calc R 1 . . H
H14D 1.7603 -0.0568 0.4137 0.131 Uiso calc R 1 . . H
H14E 1.8385 0.0586 0.4003 0.131 Uiso calc R 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1A C2A . 1.720(3) ?
Cl2A C3A . 1.723(3) ?
Cl3A C5A . 1.723(3) ?
Cl4A C6A . 1.721(3) ?
O1A C1A . 1.254(4) ?
O2A C4A . 1.246(4) ?
C1A C2A . 1.447(5) ?
C1A C6A . 1.453(5) ?
C2A C3A . 1.378(5) ?
C3A C4A . 1.452(4) ?
C4A C5A . 1.457(4) ?
C5A C6A . 1.365(5) ?
Cl1B C2B . 1.718(3) ?
Cl2B C3B . 1.722(3) ?
Cl3B C5B . 1.722(3) ?
Cl4B C6B . 1.720(3) ?
O1B C1B . 1.246(4) ?
O2B C4B . 1.250(4) ?
C1B C2B . 1.450(4) ?
C1B C6B . 1.453(4) ?
C2B C3B . 1.365(4) ?
C3B C4B . 1.455(4) ?
C4B C5B . 1.447(4) ?
C5B C6B . 1.366(4) ?
Cl1C C2C . 1.702(4) ?
Cl2C C3C . 1.701(4) ?
O1C C1C . 1.200(5) ?
C1C C2C . 1.480(6) ?
C1C C3C . 1.487(6) ?
C2C C3C 2_566 1.344(6) ?
C3C C2C 2_566 1.344(6) ?
O3A C13A . 1.200(6) ?
O4A C13A . 1.321(6) ?
O4A C14A . 1.448(6) ?
N1A C7A . 1.337(4) ?
N1A C11A . 1.348(4) ?
N1A C12A . 1.481(5) ?
C7A C8A . 1.378(5) ?
C7A H7A . 0.93 ?
C8A C9A . 1.389(5) ?
C8A C13A . 1.495(6) ?
C9A C10A . 1.358(6) ?
C9A H9A . 0.93 ?
C10A C11A . 1.376(6) ?
C10A H10A . 0.93 ?
C11A H11A . 0.93 ?
C12A H12A . 0.96 ?
C12A H12B . 0.96 ?
C12A H12C . 0.96 ?
C14A H14C . 0.96 ?
C14A H14A . 0.96 ?
C14A H14B . 0.96 ?
O3B C13B . 1.195(6) ?
O4B C13B . 1.315(5) ?
O4B C14B . 1.441(5) ?
N1B C11B . 1.337(4) ?
N1B C7B . 1.341(4) ?
N1B C12B . 1.479(5) ?
C7B C8B . 1.380(5) ?
C7B H7B . 0.93 ?
C8B C9B . 1.393(5) ?
C8B C13B . 1.489(5) ?
C9B C10B . 1.360(6) ?
C9B H9B . 0.93 ?
C10B C11B . 1.380(6) ?
C10B H10B . 0.93 ?
C11B H11B . 0.93 ?
C12B H12D . 0.96 ?
C12B H12F . 0.96 ?
C12B H12E . 0.96 ?
C14B H14F . 0.96 ?
C14B H14D . 0.96 ?
C14B H14E . 0.96 ?

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
O1A C1A C2A 122.7(3) . . ?
O1A C1A C6A 122.7(3) . . ?
C2A C1A C6A 114.5(3) . . ?
C3A C2A C1A 122.5(3) . . ?
C3A C2A Cl1A 121.2(3) . . ?
C1A C2A Cl1A 116.4(2) . . ?
C2A C3A C4A 123.0(3) . . ?
C2A C3A Cl2A 120.9(3) . . ?
C4A C3A Cl2A 116.0(2) . . ?
O2A C4A C3A 123.0(3) . . ?
O2A C4A C5A 123.1(3) . . ?
C3A C4A C5A 113.9(3) . . ?
C6A C5A C4A 123.1(3) . . ?
C6A C5A Cl3A 120.7(3) . . ?
C4A C5A Cl3A 116.2(2) . . ?
C5A C6A C1A 122.7(3) . . ?
C5A C6A Cl4A 121.1(3) . . ?
C1A C6A Cl4A 116.2(2) . . ?
O1B C1B C2B 122.9(3) . . ?
O1B C1B C6B 122.6(3) . . ?
C2B C1B C6B 114.5(3) . . ?
C3B C2B C1B 122.5(3) . . ?
C3B C2B Cl1B 121.9(2) . . ?
C1B C2B Cl1B 115.6(2) . . ?
C2B C3B C4B 122.9(3) . . ?
C2B C3B Cl2B 121.3(2) . . ?
C4B C3B Cl2B 115.8(2) . . ?
O2B C4B C5B 122.9(3) . . ?
O2B C4B C3B 122.4(3) . . ?
C5B C4B C3B 114.6(3) . . ?
C6B C5B C4B 122.5(3) . . ?
C6B C5B Cl3B 121.6(2) . . ?
C4B C5B Cl3B 115.9(2) . . ?
C5B C6B C1B 123.0(3) . . ?
C5B C6B Cl4B 121.6(2) . . ?
C1B C6B Cl4B 115.4(2) . . ?
O1C C1C C2C 121.7(4) . . ?
O1C C1C C3C 121.3(4) . . ?
C2C C1C C3C 116.9(3) . . ?
C3C C2C C1C 121.3(4) 2_566 . ?
C3C C2C Cl1C 122.9(3) 2_566 . ?
C1C C2C Cl1C 115.7(3) . . ?
C2C C3C C1C 121.7(4) 2_566 . ?
C2C C3C Cl2C 122.6(3) 2_566 . ?
C1C C3C Cl2C 115.7(3) . . ?
C13A O4A C14A 115.5(4) . . ?
C7A N1A C11A 121.1(3) . . ?
C7A N1A C12A 119.4(3) . . ?
C11A N1A C12A 119.5(3) . . ?
N1A C7A C8A 120.2(3) . . ?
N1A C7A H7A 119.9 . . ?
C8A C7A H7A 119.9 . . ?
C7A C8A C9A 118.8(3) . . ?
C7A C8A C13A 120.4(3) . . ?
C9A C8A C13A 120.7(4) . . ?
C10A C9A C8A 120.2(4) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 119.2(3) . . ?
C9A C10A H10A 120.4 . . ?
C11A C10A H10A 120.4 . . ?
N1A C11A C10A 120.4(3) . . ?
N1A C11A H11A 119.8 . . ?
C10A C11A H11A 119.8 . . ?
N1A C12A H12A 109.5 . . ?
N1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
N1A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
O3A C13A O4A 125.5(4) . . ?
O3A C13A C8A 123.3(4) . . ?
O4A C13A C8A 111.2(4) . . ?
O4A C14A H14C 109.5 . . ?
O4A C14A H14A 109.5 . . ?
H14C C14A H14A 109.5 . . ?
O4A C14A H14B 109.5 . . ?
H14C C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13B O4B C14B 117.4(4) . . ?
C11B N1B C7B 121.1(3) . . ?
C11B N1B C12B 120.3(3) . . ?
C7B N1B C12B 118.5(3) . . ?
N1B C7B C8B 120.4(3) . . ?
N1B C7B H7B 119.8 . . ?
C8B C7B H7B 119.8 . . ?
C7B C8B C9B 118.8(3) . . ?
C7B C8B C13B 120.3(3) . . ?
C9B C8B C13B 120.9(3) . . ?
C10B C9B C8B 119.6(4) . . ?
C10B C9B H9B 120.2 . . ?
C8B C9B H9B 120.2 . . ?
C9B C10B C11B 119.7(3) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
N1B C11B C10B 120.4(3) . . ?
N1B C11B H11B 119.8 . . ?
C10B C11B H11B 119.8 . . ?
N1B C12B H12D 109.5 . . ?
N1B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
N1B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12F C12B H12E 109.5 . . ?
O3B C13B O4B 124.5(4) . . ?
O3B C13B C8B 122.7(4) . . ?
O4B C13B C8B 112.7(3) . . ?
O4B C14B H14F 109.5 . . ?
O4B C14B H14D 109.5 . . ?
H14F C14B H14D 109.5 . . ?
O4B C14B H14E 109.5 . . ?
H14F C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?

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
O1A C1A C2A C3A 177.1(3) . . . . ?
C6A C1A C2A C3A -5.8(5) . . . . ?
O1A C1A C2A Cl1A -3.7(4) . . . . ?
C6A C1A C2A Cl1A 173.4(2) . . . . ?
C1A C2A C3A C4A 2.1(5) . . . . ?
Cl1A C2A C3A C4A -177.1(2) . . . . ?
C1A C2A C3A Cl2A 178.8(2) . . . . ?
Cl1A C2A C3A Cl2A -0.4(4) . . . . ?
C2A C3A C4A O2A -179.9(3) . . . . ?
Cl2A C3A C4A O2A 3.2(4) . . . . ?
C2A C3A C4A C5A 2.4(5) . . . . ?
Cl2A C3A C4A C5A -174.5(2) . . . . ?
O2A C4A C5A C6A 179.4(3) . . . . ?
C3A C4A C5A C6A -2.9(5) . . . . ?
O2A C4A C5A Cl3A -2.8(4) . . . . ?
C3A C4A C5A Cl3A 174.9(2) . . . . ?
C4A C5A C6A C1A -1.1(5) . . . . ?
Cl3A C5A C6A C1A -178.8(2) . . . . ?
C4A C5A C6A Cl4A 177.3(2) . . . . ?
Cl3A C5A C6A Cl4A -0.4(4) . . . . ?
O1A C1A C6A C5A -177.6(3) . . . . ?
C2A C1A C6A C5A 5.3(5) . . . . ?
O1A C1A C6A Cl4A 4.0(4) . . . . ?
C2A C1A C6A Cl4A -173.1(2) . . . . ?
O1B C1B C2B C3B -177.3(3) . . . . ?
C6B C1B C2B C3B 3.6(5) . . . . ?
O1B C1B C2B Cl1B 5.5(4) . . . . ?
C6B C1B C2B Cl1B -173.6(2) . . . . ?
C1B C2B C3B C4B -1.3(5) . . . . ?
Cl1B C2B C3B C4B 175.7(2) . . . . ?
C1B C2B C3B Cl2B 178.9(2) . . . . ?
Cl1B C2B C3B Cl2B -4.1(4) . . . . ?
C2B C3B C4B O2B -179.0(3) . . . . ?
Cl2B C3B C4B O2B 0.8(4) . . . . ?
C2B C3B C4B C5B -1.1(5) . . . . ?
Cl2B C3B C4B C5B 178.7(2) . . . . ?
O2B C4B C5B C6B 178.9(3) . . . . ?
C3B C4B C5B C6B 1.0(5) . . . . ?
O2B C4B C5B Cl3B 0.3(4) . . . . ?
C3B C4B C5B Cl3B -177.6(2) . . . . ?
C4B C5B C6B C1B 1.6(5) . . . . ?
Cl3B C5B C6B C1B -180.0(2) . . . . ?
C4B C5B C6B Cl4B -176.7(2) . . . . ?
Cl3B C5B C6B Cl4B 1.8(4) . . . . ?
O1B C1B C6B C5B 177.2(3) . . . . ?
C2B C1B C6B C5B -3.8(5) . . . . ?
O1B C1B C6B Cl4B -4.5(4) . . . . ?
C2B C1B C6B Cl4B 174.6(2) . . . . ?
O1C C1C C2C C3C -176.0(4) . . . 2_566 ?
C3C C1C C2C C3C 1.4(6) . . . 2_566 ?
O1C C1C C2C Cl1C 2.9(6) . . . . ?
C3C C1C C2C Cl1C -179.7(3) . . . . ?
O1C C1C C3C C2C 176.0(4) . . . 2_566 ?
C2C C1C C3C C2C -1.4(6) . . . 2_566 ?
O1C C1C C3C Cl2C -3.0(6) . . . . ?
C2C C1C C3C Cl2C 179.5(3) . . . . ?
C11A N1A C7A C8A 2.4(5) . . . . ?
C12A N1A C7A C8A -176.1(3) . . . . ?
N1A C7A C8A C9A -0.7(5) . . . . ?
N1A C7A C8A C13A 177.8(3) . . . . ?
C7A C8A C9A C10A -1.1(6) . . . . ?
C13A C8A C9A C10A -179.6(4) . . . . ?
C8A C9A C10A C11A 1.2(7) . . . . ?
C7A N1A C11A C10A -2.3(6) . . . . ?
C12A N1A C11A C10A 176.2(4) . . . . ?
C9A C10A C11A N1A 0.5(6) . . . . ?
C14A O4A C13A O3A 3.5(8) . . . . ?
C14A O4A C13A C8A -174.3(5) . . . . ?
C7A C8A C13A O3A -162.0(4) . . . . ?
C9A C8A C13A O3A 16.5(7) . . . . ?
C7A C8A C13A O4A 15.8(6) . . . . ?
C9A C8A C13A O4A -165.7(4) . . . . ?
C11B N1B C7B C8B -0.4(5) . . . . ?
C12B N1B C7B C8B 177.1(3) . . . . ?
N1B C7B C8B C9B 0.6(5) . . . . ?
N1B C7B C8B C13B -179.4(3) . . . . ?
C7B C8B C9B C10B 0.0(6) . . . . ?
C13B C8B C9B C10B -180.0(4) . . . . ?
C8B C9B C10B C11B -0.8(7) . . . . ?
C7B N1B C11B C10B -0.4(5) . . . . ?
C12B N1B C11B C10B -177.9(4) . . . . ?
C9B C10B C11B N1B 1.0(6) . . . . ?
C14B O4B C13B O3B 2.3(9) . . . . ?
C14B O4B C13B C8B 179.5(5) . . . . ?
C7B C8B C13B O3B -173.6(5) . . . . ?
C9B C8B C13B O3B 6.4(7) . . . . ?
C7B C8B C13B O4B 9.1(6) . . . . ?
C9B C8B C13B O4B -170.8(4) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_br4q_pyz_3
_database_code_depnum_ccdc_archive 'CCDC 1921857'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_date             2017-03-08T11:47:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 Br4 O2, C5 H7 N2'
_chemical_formula_sum            'C11 H7 Br4 N2 O2'
_chemical_formula_weight         518.78

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   18.5984(5)
_cell_length_b                   18.6075(5)
_cell_length_c                   3.95450(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1368.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3745
_cell_measurement_theta_min      3.357
_cell_measurement_theta_max      75.7708
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    14.365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.48851
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            5689
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.023
_diffrn_reflns_theta_min         4.75
_diffrn_reflns_theta_max         75.95
_diffrn_reflns_theta_full        75.95
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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.
;
_reflns_number_total             1446
_reflns_number_gt                1386
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0641
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         1446
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0343P)²+1.1270P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.901794(15) 0.360309(16) 0.21048(8) 0.03721(12) Uani d . 1 . . Br
Br2 1.170715(14) 0.497302(16) 0.20779(8) 0.03585(12) Uani d . 1 . . Br
O1 1.05705(11) 0.38915(13) 0.3536(7) 0.0511(6) Uani d . 1 . . O
C2 0.95545(12) 0.44201(15) 0.0889(7) 0.0336(5) Uani d . 1 . . C
C1 1.03070(14) 0.44014(17) 0.1915(8) 0.0386(6) Uani d . 1 . . C
C3 1.07250(13) 0.50196(15) 0.0859(8) 0.0338(6) Uani d . 1 . . C
N1 1.12616(17) 0.25 0.8046(8) 0.0307(6) Uani d S 1 . . N
N2 1.2731(2) 0.25 0.8680(17) 0.0690(14) Uani d S 1 . . N
C4 1.16205(18) 0.31205(18) 0.8123(9) 0.0464(7) Uani d . 1 . . C
H4 1.1378 0.3556 0.7964 0.056 Uiso calc R 1 . . H
C5 1.2358(2) 0.3102(2) 0.8445(12) 0.0630(11) Uani d . 1 . . C
H5 1.2607 0.3535 0.8498 0.076 Uiso calc R 1 . . H
C6 1.0462(2) 0.25 0.7881(11) 0.0372(8) Uani d S 1 . . C
H6A 1.029 0.2014 0.784 0.056 Uiso calc PR 0.5 . . H
H6B 1.0309 0.2744 0.5869 0.056 Uiso calc PR 0.5 . . H
H6C 1.0272 0.2742 0.9829 0.056 Uiso calc PR 0.5 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.881(2) ?
Br2 C3 . 1.891(3) ?
O1 C1 . 1.246(4) ?
C2 C3 5_765 1.354(4) ?
C2 C1 . 1.457(3) ?
C1 C3 . 1.450(4) ?
C3 C2 5_765 1.354(4) ?
N1 C4 . 1.334(4) ?
N1 C4 8_565 1.334(4) ?
N1 C6 . 1.488(5) ?
N2 C5 8_565 1.320(4) ?
N2 C5 . 1.320(4) ?
C4 C5 . 1.379(5) ?
C4 H4 . 0.93 ?
C5 H5 . 0.93 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?

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
C3 C2 C1 121.9(2) 5_765 . ?
C3 C2 Br1 123.29(18) 5_765 . ?
C1 C2 Br1 114.8(2) . . ?
O1 C1 C3 122.8(2) . . ?
O1 C1 C2 122.6(3) . . ?
C3 C1 C2 114.6(2) . . ?
C2 C3 C1 123.5(2) 5_765 . ?
C2 C3 Br2 122.41(19) 5_765 . ?
C1 C3 Br2 114.08(19) . . ?
C4 N1 C4 119.9(4) . 8_565 ?
C4 N1 C6 120.06(18) . . ?
C4 N1 C6 120.06(18) 8_565 . ?
C5 N2 C5 116.0(4) 8_565 . ?
N1 C4 C5 118.6(3) . . ?
N1 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N2 C5 C4 123.4(3) . . ?
N2 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
C3 C2 C1 O1 179.7(3) 5_765 . . . ?
Br1 C2 C1 O1 -1.5(4) . . . . ?
C3 C2 C1 C3 -1.1(5) 5_765 . . . ?
Br1 C2 C1 C3 177.7(2) . . . . ?
O1 C1 C3 C2 -179.6(3) . . . 5_765 ?
C2 C1 C3 C2 1.1(5) . . . 5_765 ?
O1 C1 C3 Br2 1.2(4) . . . . ?
C2 C1 C3 Br2 -178.0(2) . . . . ?
C4 N1 C4 C5 -3.0(7) 8_565 . . . ?
C6 N1 C4 C5 176.8(4) . . . . ?
C5 N2 C5 C4 2.8(11) 8_565 . . . ?
N1 C4 C5 N2 0.0(8) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
