# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_2picddq_100k
_database_code_depnum_ccdc_archive 'CCDC 1584115'

_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;
_publcif_datablock.id            {d777b694-520f-4df7-9565-0876d4c32085}

# publcif _publ_body_element loop end

_audit_creation_date             2017-02-10T14:36:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl2 N3 O2'
_chemical_formula_sum            'C15 H10 Cl2 N3 O2'
_chemical_formula_weight         335.16

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   7.488(5)
_cell_length_b                   15.981(5)
_cell_length_c                   12.179(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 105.711(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1403.0(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    793
_cell_measurement_theta_min      4.6741
_cell_measurement_theta_max      76.7033
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    4.266
_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  0.43726
_exptl_absorpt_correction_T_max  1

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

# EXPERIMENTAL DATA

_exptl_special_details           ?
_diffrn_ambient_temperature      100(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            2652
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_theta_min         4.68
_diffrn_reflns_theta_max         76.89
_diffrn_reflns_theta_full        76.89
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       15

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

# 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             1413
_reflns_number_gt                1114
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.189
_refine_ls_R_factor_gt           0.17
_refine_ls_wR_factor_ref         0.4811
_refine_ls_goodness_of_fit_ref   1.89
_refine_ls_restrained_S_all      1.908
_refine_ls_number_reflns         1413
_refine_ls_number_parameters     136
_refine_ls_number_restraints     224
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.311
_refine_diff_density_min         -0.94
_refine_diff_density_rms         0.212
_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 -0.0884(3) 0.17638(13) 0.1165(2) 0.0492(11) Uani d U 1 . . Cl
O1 0.0382(8) 0.0055(3) 0.1910(6) 0.0349(16) Uani d U 1 . . O
N1 -0.0614(14) -0.2015(6) 0.1501(10) 0.057(2) Uani d DU 1 . . N
C1 -0.0938(10) 0.0062(5) 0.1054(7) 0.0285(19) Uani d U 1 . . C
C2 -0.1798(10) -0.0707(5) 0.0486(7) 0.0296(17) Uani d DU 1 . . C
C3 -0.1807(11) 0.0826(5) 0.0466(7) 0.0304(18) Uani d U 1 . . C
C4 -0.1040(10) -0.1549(6) 0.1078(7) 0.0351(19) Uani d DU 1 . . C
C8 0.0609(12) 0.6212(5) 0.0545(8) 0.027(3) Uani d PGDU 0.5 . . C
C9 0.1226(12) 0.5457(5) 0.1080(6) 0.024(3) Uani d PGDU 0.5 . . C
N2 0.0605(11) 0.4706(5) 0.0534(7) 0.029(3) Uani d PGDU 0.5 . . N
C5 -0.0634(11) 0.4709(5) -0.0546(7) 0.018(3) Uani d PGDU 0.5 . . C
C6 -0.1252(13) 0.5465(5) -0.1082(6) 0.027(3) Uani d PGDU 0.5 . . C
C7 -0.0630(13) 0.6216(4) -0.0536(8) 0.028(3) Uani d PGDU 0.5 . . C
C10 0.120(2) 0.3865(9) 0.1120(14) 0.031(3) Uani d PDU 0.5 . . C
H10A 0.0559 0.342 0.0641 0.046 Uiso calc PR 0.5 . . H
H10B 0.0893 0.3851 0.1836 0.046 Uiso calc PR 0.5 . . H
H10C 0.2511 0.3795 0.1249 0.046 Uiso calc PR 0.5 . . H
C11 -0.124(2) 0.3895(8) -0.1137(14) 0.026(3) Uani d PDU 0.5 . . C
H11A -0.0665 0.3441 -0.0653 0.04 Uiso calc PR 0.5 . . H
H11B -0.0886 0.3875 -0.1837 0.04 Uiso calc PR 0.5 . . H
H11C -0.2566 0.3845 -0.13 0.04 Uiso calc PR 0.5 . . H
H9 0.205(7) 0.543(4) 0.180(3) 0.05 Uiso d PD 0.5 . . H
H6 -0.207(7) 0.542(4) -0.181(3) 0.05 Uiso d PD 0.5 . . H
H7 -0.106(8) 0.6719(19) -0.088(4) 0.05 Uiso d PD 0.5 . . H
H8 0.101(8) 0.6707(19) 0.092(4) 0.05 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 C3 . 1.769(8) ?
O1 C1 . 1.227(9) ?
N1 C4 . 0.913(12) ?
C1 C2 . 1.472(9) ?
C1 C3 . 1.474(10) ?
C2 C2 2_455 1.354(15) ?
C2 C4 . 1.558(10) ?
C3 C3 2_455 1.315(15) ?
C8 C11 5_565 0.768(18) ?
C8 C9 . 1.39 ?
C8 C7 . 1.39 ?
C8 C5 5_565 1.473(14) ?
C8 H8 . 0.922(18) ?
C9 C5 5_565 0.730(12) ?
C9 C11 5_565 1.039(16) ?
C9 N2 . 1.39 ?
C9 C6 5_565 1.473(17) ?
C9 H9 . 0.93(2) ?
N2 C6 5_565 0.760(13) ?
N2 C5 5_565 0.935(14) ?
N2 C5 . 1.39 ?
N2 C7 5_565 1.473(14) ?
N2 C10 . 1.529(12) ?
N2 N2 5_565 1.662(13) ?
C5 C9 5_565 0.730(12) ?
C5 N2 5_565 0.935(14) ?
C5 C6 . 1.39 ?
C5 C8 5_565 1.473(13) ?
C5 C11 . 1.498(12) ?
C5 C5 5_565 1.689(12) ?
C5 C7 5_565 2.036(16) ?
C6 N2 5_565 0.760(12) ?
C6 C10 5_565 1.074(18) ?
C6 C7 . 1.39 ?
C6 C9 5_565 1.473(17) ?
C6 H6 . 0.93(2) ?
C7 C10 5_565 0.734(18) ?
C7 N2 5_565 1.473(14) ?
C7 C5 5_565 2.036(14) ?
C7 H7 . 0.923(18) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
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(7) . . ?
O1 C1 C3 124.7(7) . . ?
C2 C1 C3 112.6(7) . . ?
C2 C2 C1 123.3(4) 2_455 . ?
C2 C2 C4 120.2(4) 2_455 . ?
C1 C2 C4 116.5(6) . . ?
C3 C3 C1 124.1(4) 2_455 . ?
C3 C3 Cl1 122.0(3) 2_455 . ?
C1 C3 Cl1 113.9(5) . . ?
N1 C4 C2 173.3(12) . . ?
C11 C8 C9 47.5(12) 5_565 . ?
C11 C8 C7 167.2(12) 5_565 . ?
C9 C8 C7 120 . . ?
C11 C8 C5 76.8(12) 5_565 5_565 ?
C9 C8 C5 29.4(5) . 5_565 ?
C7 C8 C5 90.6(5) . 5_565 ?
C11 C8 H8 72(3) 5_565 . ?
C9 C8 H8 119(3) . . ?
C7 C8 H8 121(3) . . ?
C5 C8 H8 149(3) 5_565 . ?
C5 C9 C11 114.6(16) 5_565 5_565 ?
C5 C9 N2 38.4(11) 5_565 . ?
C11 C9 N2 152.9(10) 5_565 . ?
C5 C9 C8 81.6(11) 5_565 . ?
C11 C9 C8 33.0(10) 5_565 . ?
N2 C9 C8 120 . . ?
C5 C9 C6 69.0(13) 5_565 5_565 ?
C11 C9 C6 176.2(13) 5_565 5_565 ?
N2 C9 C6 30.6(6) . 5_565 ?
C8 C9 C6 150.6(6) . 5_565 ?
C5 C9 H9 156(5) 5_565 . ?
C11 C9 H9 89(4) 5_565 . ?
N2 C9 H9 118(4) . . ?
C8 C9 H9 122(4) . . ?
C6 C9 H9 87(4) 5_565 . ?
C6 N2 C5 109.7(17) 5_565 5_565 ?
C6 N2 C9 80.7(14) 5_565 . ?
C5 N2 C9 29.0(7) 5_565 . ?
C6 N2 C5 159.3(14) 5_565 . ?
C5 N2 C5 91.0(7) 5_565 . ?
C9 N2 C5 120 . . ?
C6 N2 C7 68.7(10) 5_565 5_565 ?
C5 N2 C7 177.9(15) 5_565 5_565 ?
C9 N2 C7 149.4(9) . 5_565 ?
C5 N2 C7 90.6(9) . 5_565 ?
C6 N2 C10 40.7(13) 5_565 . ?
C5 N2 C10 150.3(11) 5_565 . ?
C9 N2 C10 121.3(7) . . ?
C5 N2 C10 118.7(7) . . ?
C7 N2 C10 28.2(9) 5_565 . ?
C6 N2 N2 166.4(16) 5_565 5_565 ?
C5 N2 N2 56.7(7) 5_565 5_565 ?
C9 N2 N2 85.8(5) . 5_565 ?
C5 N2 N2 34.2(5) . 5_565 ?
C7 N2 N2 124.9(10) 5_565 5_565 ?
C10 N2 N2 152.9(9) . 5_565 ?
C9 C5 N2 112.6(18) 5_565 5_565 ?
C9 C5 C6 81.6(15) 5_565 . ?
N2 C5 C6 31.0(7) 5_565 . ?
C9 C5 N2 158.4(15) 5_565 . ?
N2 C5 N2 89.0(7) 5_565 . ?
C6 C5 N2 120 . . ?
C9 C5 C8 69.0(13) 5_565 5_565 ?
N2 C5 C8 177.9(12) 5_565 5_565 ?
C6 C5 C8 150.6(5) . 5_565 ?
N2 C5 C8 89.4(5) . 5_565 ?
C9 C5 C11 39.1(13) 5_565 . ?
N2 C5 C11 151.6(12) 5_565 . ?
C6 C5 C11 120.7(7) . . ?
N2 C5 C11 119.3(7) . . ?
C8 C5 C11 29.9(7) 5_565 . ?
C9 C5 C5 167.9(17) 5_565 5_565 ?
N2 C5 C5 55.4(6) 5_565 5_565 ?
C6 C5 C5 86.4(5) . 5_565 ?
N2 C5 C5 33.6(5) . 5_565 ?
C8 C5 C5 123.0(8) 5_565 5_565 ?
C11 C5 C5 152.8(9) . 5_565 ?
C9 C5 C7 112.1(14) 5_565 5_565 ?
N2 C5 C7 135.3(11) 5_565 5_565 ?
C6 C5 C7 166.3(6) . 5_565 ?
N2 C5 C7 46.3(6) . 5_565 ?
C8 C5 C7 43.1(5) 5_565 5_565 ?
C11 C5 C7 73.0(8) . 5_565 ?
C5 C5 C7 79.9(6) 5_565 5_565 ?
N2 C6 C10 111.8(15) 5_565 5_565 ?
N2 C6 C5 39.3(10) 5_565 . ?
C10 C6 C5 151.0(10) 5_565 . ?
N2 C6 C7 80.7(11) 5_565 . ?
C10 C6 C7 31.4(10) 5_565 . ?
C5 C6 C7 120 . . ?
N2 C6 C9 68.7(12) 5_565 5_565 ?
C10 C6 C9 175.7(18) 5_565 5_565 ?
C5 C6 C9 29.4(6) . 5_565 ?
C7 C6 C9 149.4(6) . 5_565 ?
N2 C6 H6 155(4) 5_565 . ?
C10 C6 H6 93(4) 5_565 . ?
C5 C6 H6 116(4) . . ?
C7 C6 H6 124(4) . . ?
C9 C6 H6 86(4) 5_565 . ?
C10 C7 C6 49.8(14) 5_565 . ?
C10 C7 C8 168.3(14) 5_565 . ?
C6 C7 C8 120 . . ?
C10 C7 N2 80.2(14) 5_565 5_565 ?
C6 C7 N2 30.6(5) . 5_565 ?
C8 C7 N2 89.4(5) . 5_565 ?
C10 C7 C5 123.0(15) 5_565 5_565 ?
C6 C7 C5 73.7(4) . 5_565 ?
C8 C7 C5 46.3(4) . 5_565 ?
N2 C7 C5 43.0(4) 5_565 5_565 ?
C10 C7 H7 71(3) 5_565 . ?
C6 C7 H7 120(3) . . ?
C8 C7 H7 120(3) . . ?
N2 C7 H7 151(3) 5_565 . ?
C5 C7 H7 166(3) 5_565 . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 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 C2 -177.1(10) . . . 2_455 ?
C3 C1 C2 C2 1.6(15) . . . 2_455 ?
O1 C1 C2 C4 4.3(12) . . . . ?
C3 C1 C2 C4 -177.0(6) . . . . ?
O1 C1 C3 C3 178.3(10) . . . 2_455 ?
C2 C1 C3 C3 -0.3(16) . . . 2_455 ?
O1 C1 C3 Cl1 -4.3(12) . . . . ?
C2 C1 C3 Cl1 177.1(5) . . . . ?
C2 C2 C4 N1 -129(9) 2_455 . . . ?
C1 C2 C4 N1 50(9) . . . . ?
C11 C8 C9 C5 178(3) 5_565 . . 5_565 ?
C7 C8 C9 C5 1.0(13) . . . 5_565 ?
C7 C8 C9 C11 -177(2) . . . 5_565 ?
C5 C8 C9 C11 -178(3) 5_565 . . 5_565 ?
C11 C8 C9 N2 177(2) 5_565 . . . ?
C7 C8 C9 N2 0 . . . . ?
C5 C8 C9 N2 -1.0(13) 5_565 . . . ?
C11 C8 C9 C6 178(3) 5_565 . . 5_565 ?
C7 C8 C9 C6 1(2) . . . 5_565 ?
C5 C8 C9 C6 0.0(12) 5_565 . . 5_565 ?
C5 C9 N2 C6 177(4) 5_565 . . 5_565 ?
C11 C9 N2 C6 -177(4) 5_565 . . 5_565 ?
C8 C9 N2 C6 179(2) . . . 5_565 ?
C11 C9 N2 C5 5(2) 5_565 . . 5_565 ?
C8 C9 N2 C5 2(2) . . . 5_565 ?
C6 C9 N2 C5 -177(4) 5_565 . . 5_565 ?
C5 C9 N2 C5 -2(2) 5_565 . . . ?
C11 C9 N2 C5 4(3) 5_565 . . . ?
C8 C9 N2 C5 0 . . . . ?
C6 C9 N2 C5 -179(2) 5_565 . . . ?
C5 C9 N2 C7 177(4) 5_565 . . 5_565 ?
C11 C9 N2 C7 -177(3) 5_565 . . 5_565 ?
C8 C9 N2 C7 179(2) . . . 5_565 ?
C6 C9 N2 C7 0.0(11) 5_565 . . 5_565 ?
C5 C9 N2 C10 -179(3) 5_565 . . . ?
C11 C9 N2 C10 -174(3) 5_565 . . . ?
C8 C9 N2 C10 -177.5(10) . . . . ?
C6 C9 N2 C10 3.5(16) 5_565 . . . ?
C5 C9 N2 N2 -1.2(19) 5_565 . . 5_565 ?
C11 C9 N2 N2 4(3) 5_565 . . 5_565 ?
C8 C9 N2 N2 0.4(5) . . . 5_565 ?
C6 C9 N2 N2 -179(2) 5_565 . . 5_565 ?
C6 N2 C5 C9 0(8) 5_565 . . 5_565 ?
C5 N2 C5 C9 176(6) 5_565 . . 5_565 ?
C9 N2 C5 C9 177(5) . . . 5_565 ?
C7 N2 C5 C9 -2(5) 5_565 . . 5_565 ?
C10 N2 C5 C9 -5(5) . . . 5_565 ?
N2 N2 C5 C9 176(6) 5_565 . . 5_565 ?
C6 N2 C5 N2 -176(6) 5_565 . . 5_565 ?
C5 N2 C5 N2 0.0(11) 5_565 . . 5_565 ?
C9 N2 C5 N2 0.8(10) . . . 5_565 ?
C7 N2 C5 N2 -178.7(16) 5_565 . . 5_565 ?
C10 N2 C5 N2 178.4(13) . . . 5_565 ?
C6 N2 C5 C6 -177(6) 5_565 . . . ?
C5 N2 C5 C6 -0.8(10) 5_565 . . . ?
C9 N2 C5 C6 0 . . . . ?
C7 N2 C5 C6 -179.5(11) 5_565 . . . ?
C10 N2 C5 C6 177.6(10) . . . . ?
N2 N2 C5 C6 -0.8(10) 5_565 . . . ?
C6 N2 C5 C8 2(5) 5_565 . . 5_565 ?
C5 N2 C5 C8 178.7(14) 5_565 . . 5_565 ?
C9 N2 C5 C8 179.5(5) . . . 5_565 ?
C7 N2 C5 C8 0.0(8) 5_565 . . 5_565 ?
C10 N2 C5 C8 -2.9(9) . . . 5_565 ?
N2 N2 C5 C8 178.7(14) 5_565 . . 5_565 ?
C6 N2 C5 C11 1(6) 5_565 . . . ?
C5 N2 C5 C11 177.3(13) 5_565 . . . ?
C9 N2 C5 C11 178.1(9) . . . . ?
C7 N2 C5 C11 -1.4(11) 5_565 . . . ?
C10 N2 C5 C11 -4.4(13) . . . . ?
N2 N2 C5 C11 177.3(16) 5_565 . . . ?
C6 N2 C5 C5 -176(6) 5_565 . . 5_565 ?
C9 N2 C5 C5 0.8(10) . . . 5_565 ?
C7 N2 C5 C5 -178.7(19) 5_565 . . 5_565 ?
C10 N2 C5 C5 178.4(16) . . . 5_565 ?
N2 N2 C5 C5 0.0(11) 5_565 . . 5_565 ?
C6 N2 C5 C7 2(5) 5_565 . . 5_565 ?
C5 N2 C5 C7 178.7(19) 5_565 . . 5_565 ?
C9 N2 C5 C7 179.5(11) . . . 5_565 ?
C10 N2 C5 C7 -2.9(9) . . . 5_565 ?
N2 N2 C5 C7 178.7(16) 5_565 . . 5_565 ?
C9 C5 C6 N2 -177(4) 5_565 . . 5_565 ?
N2 C5 C6 N2 1.5(19) . . . 5_565 ?
C8 C5 C6 N2 -177(3) 5_565 . . 5_565 ?
C11 C5 C6 N2 -177(2) . . . 5_565 ?
C5 C5 C6 N2 1.1(18) 5_565 . . 5_565 ?
C7 C5 C6 N2 0(4) 5_565 . . 5_565 ?
C9 C5 C6 C10 -171(4) 5_565 . . 5_565 ?
N2 C5 C6 C10 6(2) 5_565 . . 5_565 ?
N2 C5 C6 C10 8(2) . . . 5_565 ?
C8 C5 C6 C10 -171(3) 5_565 . . 5_565 ?
C11 C5 C6 C10 -170(3) . . . 5_565 ?
C5 C5 C6 C10 7(2) 5_565 . . 5_565 ?
C7 C5 C6 C10 6(5) 5_565 . . 5_565 ?
C9 C5 C6 C7 -179(2) 5_565 . . . ?
N2 C5 C6 C7 -1.5(19) 5_565 . . . ?
N2 C5 C6 C7 0 . . . . ?
C8 C5 C6 C7 -179.0(11) 5_565 . . . ?
C11 C5 C6 C7 -178.0(10) . . . . ?
C5 C5 C6 C7 -0.4(5) 5_565 . . . ?
C7 C5 C6 C7 -2(3) 5_565 . . . ?
N2 C5 C6 C9 177(4) 5_565 . . 5_565 ?
N2 C5 C6 C9 179(2) . . . 5_565 ?
C8 C5 C6 C9 0.0(15) 5_565 . . 5_565 ?
C11 C5 C6 C9 0.9(16) . . . 5_565 ?
C5 C5 C6 C9 179(2) 5_565 . . 5_565 ?
C7 C5 C6 C9 177(5) 5_565 . . 5_565 ?
N2 C6 C7 C10 172(3) 5_565 . . 5_565 ?
C5 C6 C7 C10 173(2) . . . 5_565 ?
C9 C6 C7 C10 172(3) 5_565 . . 5_565 ?
N2 C6 C7 C8 -1.0(12) 5_565 . . . ?
C10 C6 C7 C8 -173(2) 5_565 . . . ?
C5 C6 C7 C8 0 . . . . ?
C9 C6 C7 C8 -1.0(19) 5_565 . . . ?
C10 C6 C7 N2 -172(3) 5_565 . . 5_565 ?
C5 C6 C7 N2 1.0(12) . . . 5_565 ?
C9 C6 C7 N2 0.0(11) 5_565 . . 5_565 ?
N2 C6 C7 C5 -0.6(11) 5_565 . . 5_565 ?
C10 C6 C7 C5 -172(2) 5_565 . . 5_565 ?
C5 C6 C7 C5 0.4(5) . . . 5_565 ?
C9 C6 C7 C5 -1(2) 5_565 . . 5_565 ?
C11 C8 C7 C10 -38(11) 5_565 . . 5_565 ?
C9 C8 C7 C10 -28(8) . . . 5_565 ?
C5 C8 C7 C10 -27(8) 5_565 . . 5_565 ?
C11 C8 C7 C6 -11(7) 5_565 . . . ?
C9 C8 C7 C6 0 . . . . ?
C5 C8 C7 C6 0.5(6) 5_565 . . . ?
C11 C8 C7 N2 -11(7) 5_565 . . 5_565 ?
C9 C8 C7 N2 -0.5(6) . . . 5_565 ?
C5 C8 C7 N2 0.0(7) 5_565 . . 5_565 ?
C11 C8 C7 C5 -11(7) 5_565 . . 5_565 ?
C9 C8 C7 C5 -0.5(6) . . . 5_565 ?



# start Validation Reply Form


_vrf_PLAT084_I                   
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................    0.48 Report
RESPONSE: High wR2 value is due to the disorder. Several data sets were
collected at RT and 100 K, and all were extremely poor. The 2-picolinium
cation is disordered about the inversion centre, yielding two poorly-
resolved positions (p.p. 0.5), which could be refined only using severe
geometric restraints. Also, the DDQ anion is possibly disordered, but the
minor component of the disorder could not be properly modelled.
;

_vrf_PLAT430_I                   
;
PROBLEM: Short Inter D...A Contact  N2     ..  N2      ..      1.66 Ang.  
RESPONSE: The 2-picoliniun cation is disordered about the inversion 
centre, so the unrealistically close contact is between two symmetry-
equivalent disordered parts.
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_inikddq-1
_database_code_depnum_ccdc_archive 'CCDC 1584117'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2016-11-30T14:58:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H10 Cl2 N3 O4'
_chemical_formula_sum            'C16 H10 Cl2 N3 O4'
_chemical_formula_weight         379.17

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7214(8)
_cell_length_b                   6.9671(4)
_cell_length_c                   20.6410(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.414(6)
_cell_angle_gamma                90
_cell_volume                     1639.64(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3554
_cell_measurement_theta_min      3.8738
_cell_measurement_theta_max      75.4775
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             772
_exptl_absorpt_coefficient_mu    3.82
_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  0.78224
_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            7051
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_theta_min         3.99
_diffrn_reflns_theta_max         75.66
_diffrn_reflns_theta_full        75.66
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

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

# 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             3242
_reflns_number_gt                3053
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0963
_refine_ls_wR_factor_ref         0.2569
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1074P)²+4.8813P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.893
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.096
_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, 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 0.25073(13) 0.5997(2) -0.08274(8) 0.0678(5) Uani d . 1 . . Cl
Cl2 0.38577(14) 0.6463(2) 0.06805(7) 0.0639(4) Uani d . 1 . . Cl
O1 0.6154(3) 0.8490(5) 0.08239(15) 0.0532(9) Uani d . 1 . . O
O2 0.3872(4) 0.7520(7) -0.17649(17) 0.0692(12) Uani d . 1 . . O
N1 0.8159(5) 0.9842(8) -0.0047(3) 0.0611(13) Uani d . 1 . . N
N2 0.6489(6) 0.9533(9) -0.1845(4) 0.090(2) Uani d . 1 . . N
C1 0.5636(5) 0.8203(7) 0.0232(2) 0.0459(11) Uani d . 1 . . C
C2 0.6161(5) 0.8739(7) -0.0315(2) 0.0467(11) Uani d . 1 . . C
C3 0.5548(5) 0.8516(7) -0.0979(2) 0.0481(11) Uani d . 1 . . C
C4 0.4392(5) 0.7703(8) -0.1168(2) 0.0531(12) Uani d . 1 . . C
C5 0.3887(5) 0.7074(7) -0.0619(3) 0.0507(12) Uani d . 1 . . C
C6 0.4483(5) 0.7300(7) 0.0029(2) 0.0472(11) Uani d . 1 . . C
C7 0.7373(8) 0.9438(9) -0.0139(3) 0.0634(16) Uani d . 1 . . C
C8 0.6082(7) 0.9122(9) -0.1514(3) 0.0664(17) Uani d . 1 . . C
O3 1.0168(4) 0.5298(7) 0.1066(3) 0.0829(15) Uani d . 1 . . O
O4 1.1963(4) 0.6203(8) 0.1597(2) 0.0778(13) Uani d . 1 . . O
N3 0.9322(4) 1.0950(6) 0.22991(19) 0.0472(9) Uani d . 1 . . N
C9 0.8649(4) 0.9813(8) 0.1849(2) 0.0488(11) Uani d . 1 . . C
H9 0.7843 1.0013 0.1731 0.059 Uiso calc R 1 . . H
C10 0.9130(4) 0.8354(8) 0.1556(3) 0.0507(12) Uani d . 1 . . C
H10 0.8655 0.7578 0.1237 0.061 Uiso calc R 1 . . H
C11 1.0331(4) 0.8039(8) 0.1738(2) 0.0466(11) Uani d . 1 . . C
C12 1.1008(4) 0.9268(8) 0.2203(2) 0.0525(12) Uani d . 1 . . C
H12 1.1818 0.9109 0.2326 0.063 Uiso calc R 1 . . H
C13 1.0495(5) 1.0693(9) 0.2478(3) 0.0552(13) Uani d . 1 . . C
H13 1.0953 1.1502 0.2792 0.066 Uiso calc R 1 . . H
C14 0.8783(6) 1.2472(11) 0.2628(3) 0.0729(18) Uani d . 1 . . C
H14A 0.9386 1.3164 0.2933 0.109 Uiso calc R 1 . . H
H14B 0.8258 1.1903 0.2868 0.109 Uiso calc R 1 . . H
H14C 0.8355 1.3339 0.2298 0.109 Uiso calc R 1 . . H
C15 1.0922(5) 0.6433(8) 0.1467(3) 0.0541(12) Uani d . 1 . . C
C16 1.0667(8) 0.3649(12) 0.0794(5) 0.100(3) Uani d . 1 . . C
H16A 1.0049 0.2922 0.0513 0.149 Uiso calc R 1 . . H
H16B 1.1079 0.2852 0.1152 0.149 Uiso calc R 1 . . H
H16C 1.1202 0.4088 0.0537 0.149 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 C5 . 1.743(6) ?
Cl2 C6 . 1.773(5) ?
O1 C1 . 1.249(5) ?
O2 C4 . 1.248(6) ?
N1 C7 . 0.939(8) ?
N2 C8 . 0.964(8) ?
C1 C2 . 1.453(7) ?
C1 C6 . 1.461(8) ?
C2 C3 . 1.402(6) ?
C2 C7 . 1.466(10) ?
C3 C4 . 1.436(8) ?
C3 C8 . 1.451(9) ?
C4 C5 . 1.462(8) ?
C5 C6 . 1.368(7) ?
O3 C15 . 1.324(7) ?
O3 C16 . 1.460(8) ?
O4 C15 . 1.198(7) ?
N3 C9 . 1.332(6) ?
N3 C13 . 1.351(7) ?
N3 C14 . 1.478(7) ?
C9 C10 . 1.369(7) ?
C9 H9 . 0.93 ?
C10 C11 . 1.388(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.389(7) ?
C11 C15 . 1.492(8) ?
C12 C13 . 1.351(8) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 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 121.4(5) . . ?
O1 C1 C6 123.8(5) . . ?
C2 C1 C6 114.8(4) . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 C7 121.8(5) . . ?
C1 C2 C7 117.0(4) . . ?
C2 C3 C4 123.1(5) . . ?
C2 C3 C8 119.8(5) . . ?
C4 C3 C8 117.0(5) . . ?
O2 C4 C3 121.5(5) . . ?
O2 C4 C5 122.8(5) . . ?
C3 C4 C5 115.8(4) . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 Cl1 121.6(5) . . ?
C4 C5 Cl1 117.3(4) . . ?
C5 C6 C1 123.9(5) . . ?
C5 C6 Cl2 119.8(4) . . ?
C1 C6 Cl2 116.3(3) . . ?
N1 C7 C2 176.6(7) . . ?
N2 C8 C3 175.9(9) . . ?
C15 O3 C16 116.2(5) . . ?
C9 N3 C13 120.8(5) . . ?
C9 N3 C14 120.0(5) . . ?
C13 N3 C14 119.1(4) . . ?
N3 C9 C10 120.8(5) . . ?
N3 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 119.6(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 118.1(5) . . ?
C10 C11 C15 123.2(5) . . ?
C12 C11 C15 118.7(5) . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N3 C13 C12 120.5(5) . . ?
N3 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 123.9(5) . . ?
O4 C15 C11 123.7(5) . . ?
O3 C15 C11 112.4(5) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 -176.3(5) . . . . ?
C6 C1 C2 C3 4.4(6) . . . . ?
O1 C1 C2 C7 6.4(7) . . . . ?
C6 C1 C2 C7 -172.9(4) . . . . ?
C1 C2 C3 C4 -1.9(7) . . . . ?
C7 C2 C3 C4 175.3(5) . . . . ?
C1 C2 C3 C8 178.0(5) . . . . ?
C7 C2 C3 C8 -4.8(7) . . . . ?
C2 C3 C4 O2 -179.8(5) . . . . ?
C8 C3 C4 O2 0.2(8) . . . . ?
C2 C3 C4 C5 -1.1(7) . . . . ?
C8 C3 C4 C5 178.9(5) . . . . ?
O2 C4 C5 C6 -180.0(5) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
O2 C4 C5 Cl1 1.0(7) . . . . ?
C3 C4 C5 Cl1 -177.7(4) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
Cl1 C5 C6 C1 -179.6(4) . . . . ?
C4 C5 C6 Cl2 -178.4(4) . . . . ?
Cl1 C5 C6 Cl2 0.7(6) . . . . ?
O1 C1 C6 C5 176.5(5) . . . . ?
C2 C1 C6 C5 -4.3(7) . . . . ?
O1 C1 C6 Cl2 -3.8(6) . . . . ?
C2 C1 C6 Cl2 175.5(3) . . . . ?
C3 C2 C7 N1 -40(14) . . . . ?
C1 C2 C7 N1 138(13) . . . . ?
C2 C3 C8 N2 12(11) . . . . ?
C4 C3 C8 N2 -168(10) . . . . ?
C13 N3 C9 C10 0.1(8) . . . . ?
C14 N3 C9 C10 -177.7(5) . . . . ?
N3 C9 C10 C11 0.9(8) . . . . ?
C9 C10 C11 C12 -1.7(8) . . . . ?
C9 C10 C11 C15 177.3(5) . . . . ?
C10 C11 C12 C13 1.6(8) . . . . ?
C15 C11 C12 C13 -177.5(5) . . . . ?
C9 N3 C13 C12 -0.3(8) . . . . ?
C14 N3 C13 C12 177.6(5) . . . . ?
C11 C12 C13 N3 -0.6(8) . . . . ?
C16 O3 C15 O4 2.2(10) . . . . ?
C16 O3 C15 C11 -178.2(6) . . . . ?
C10 C11 C15 O4 176.2(6) . . . . ?
C12 C11 C15 O4 -4.7(8) . . . . ?
C10 C11 C15 O3 -3.4(8) . . . . ?
C12 C11 C15 O3 175.6(5) . . . . ?


####################################################################### 
# 
# 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_ddq_net2pic
_database_code_depnum_ccdc_archive 'CCDC 1584119'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2016-11-30T12:12:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 Cl2 N3 O2'
_chemical_formula_sum            'C16 H12 Cl2 N3 O2'
_chemical_formula_weight         349.19

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

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P bc n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.3110(3)
_cell_length_b                   13.4662(2)
_cell_length_c                   14.4537(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3174.71(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4541
_cell_measurement_theta_min      3.2792
_cell_measurement_theta_max      75.7643
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    3.793
_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  0.60486
_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            10832
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         75.95
_diffrn_reflns_theta_full        75.95
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.99
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18

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

# 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             3285
_reflns_number_gt                2959
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1256
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.7781P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.048
_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, 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 0.68806(4) 0.91335(4) 0.03468(4) 0.06007(18) Uani d . 1 . . Cl
Cl2 0.73089(3) 1.13811(4) -0.01095(4) 0.06463(18) Uani d . 1 . . Cl
O1 0.59369(12) 1.27186(10) 0.02560(12) 0.0665(4) Uani d . 1 . . O
O2 0.52058(9) 0.88882(9) 0.10585(9) 0.0501(3) Uani d . 1 . . O
N1 0.40616(15) 1.29939(16) 0.13054(17) 0.0758(6) Uani d . 1 . . N
N2 0.35738(13) 1.01726(16) 0.20807(14) 0.0633(5) Uani d . 1 . . N
C1 0.57824(14) 1.18457(13) 0.04724(13) 0.0482(4) Uani d . 1 . . C
C2 0.50314(13) 1.15564(13) 0.09273(12) 0.0446(4) Uani d . 1 . . C
C3 0.48453(11) 1.05813(13) 0.11428(11) 0.0413(4) Uani d . 1 . . C
C4 0.53899(12) 0.97718(12) 0.09123(11) 0.0423(4) Uani d . 1 . . C
C5 0.61816(12) 1.00751(13) 0.05189(12) 0.0449(4) Uani d . 1 . . C
C6 0.63655(13) 1.10382(14) 0.03230(13) 0.0468(4) Uani d . 1 . . C
C7 0.44822(14) 1.23509(14) 0.11477(14) 0.0537(5) Uani d . 1 . . C
C8 0.41235(14) 1.03419(14) 0.16574(13) 0.0491(4) Uani d . 1 . . C
N3 0.61203(10) 0.66004(11) 0.22013(11) 0.0445(3) Uani d . 1 . . N
C9 0.58300(13) 0.66615(15) 0.13267(14) 0.0520(5) Uani d . 1 . . C
H9 0.5737 0.7282 0.1064 0.062 Uiso calc R 1 . . H
C10 0.56717(16) 0.58263(16) 0.08244(15) 0.0594(5) Uani d . 1 . . C
H10 0.5468 0.5874 0.0225 0.071 Uiso calc R 1 . . H
C11 0.58181(16) 0.49081(16) 0.12174(16) 0.0623(6) Uani d . 1 . . C
H11 0.5732 0.433 0.0879 0.075 Uiso calc R 1 . . H
C12 0.60905(15) 0.48604(15) 0.21080(16) 0.0590(5) Uani d . 1 . . C
H12 0.6171 0.4243 0.2381 0.071 Uiso calc R 1 . . H
C13 0.62493(12) 0.57116(14) 0.26150(14) 0.0476(4) Uani d . 1 . . C
C14 0.63529(16) 0.75539(16) 0.26534(17) 0.0617(6) Uani d . 1 . . C
H14A 0.624 0.7516 0.3311 0.074 Uiso calc R 1 . . H
H14B 0.6029 0.8091 0.2396 0.074 Uiso calc R 1 . . H
C15 0.72497(18) 0.7760(2) 0.2503(2) 0.0768(7) Uani d . 1 . . C
H15A 0.7394 0.8375 0.2797 0.115 Uiso calc R 1 . . H
H15B 0.7359 0.7806 0.1852 0.115 Uiso calc R 1 . . H
H15C 0.7569 0.7231 0.2765 0.115 Uiso calc R 1 . . H
C16 0.65591(18) 0.5660(2) 0.35819(16) 0.0693(6) Uani d . 1 . . C
H16A 0.6632 0.6321 0.3818 0.104 Uiso calc PR 0.5 . . H
H16B 0.7075 0.5317 0.3591 0.104 Uiso calc PR 0.5 . . H
H16C 0.6171 0.5311 0.396 0.104 Uiso calc PR 0.5 . . H
H16D 0.662 0.4978 0.3761 0.104 Uiso calc PR 0.5 . . H
H16E 0.6177 0.5982 0.3988 0.104 Uiso calc PR 0.5 . . H
H16F 0.7081 0.5988 0.362 0.104 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
Cl1 C5 . 1.7232(19) ?
Cl2 C6 . 1.724(2) ?
O1 C1 . 1.242(2) ?
O2 C4 . 1.245(2) ?
N1 C7 . 1.128(3) ?
N2 C8 . 1.109(3) ?
C1 C2 . 1.444(3) ?
C1 C6 . 1.461(3) ?
C2 C3 . 1.383(2) ?
C2 C7 . 1.431(3) ?
C3 C8 . 1.429(3) ?
C3 C4 . 1.445(2) ?
C4 C5 . 1.469(3) ?
C5 C6 . 1.361(3) ?
N3 C9 . 1.352(3) ?
N3 C13 . 1.354(2) ?
N3 C14 . 1.490(2) ?
C9 C10 . 1.363(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.363(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.93 ?
C13 C16 . 1.488(3) ?
C14 C15 . 1.505(4) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C16 H16D . 0.96 ?
C16 H16E . 0.96 ?
C16 H16F . 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 122.83(19) . . ?
O1 C1 C6 122.4(2) . . ?
C2 C1 C6 114.76(16) . . ?
C3 C2 C7 121.49(18) . . ?
C3 C2 C1 123.01(17) . . ?
C7 C2 C1 115.50(16) . . ?
C2 C3 C8 120.79(17) . . ?
C2 C3 C4 121.96(17) . . ?
C8 C3 C4 117.14(16) . . ?
O2 C4 C3 122.23(18) . . ?
O2 C4 C5 122.92(17) . . ?
C3 C4 C5 114.83(15) . . ?
C6 C5 C4 122.63(17) . . ?
C6 C5 Cl1 121.69(16) . . ?
C4 C5 Cl1 115.65(13) . . ?
C5 C6 C1 122.35(19) . . ?
C5 C6 Cl2 121.83(16) . . ?
C1 C6 Cl2 115.81(15) . . ?
N1 C7 C2 178.1(2) . . ?
N2 C8 C3 177.7(2) . . ?
C9 N3 C13 121.39(17) . . ?
C9 N3 C14 116.53(16) . . ?
C13 N3 C14 121.90(17) . . ?
N3 C9 C10 120.93(18) . . ?
N3 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.1(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 119.1(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.44(18) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
N3 C13 C12 117.95(18) . . ?
N3 C13 C16 120.57(19) . . ?
C12 C13 C16 121.48(19) . . ?
N3 C14 C15 110.1(2) . . ?
N3 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16D 109.5 . . ?
H16A C16 H16D 141.1 . . ?
H16B C16 H16D 56.3 . . ?
H16C C16 H16D 56.3 . . ?
C13 C16 H16E 109.5 . . ?
H16A C16 H16E 56.3 . . ?
H16B C16 H16E 141.1 . . ?
H16C C16 H16E 56.3 . . ?
H16D C16 H16E 109.5 . . ?
C13 C16 H16F 109.5 . . ?
H16A C16 H16F 56.3 . . ?
H16B C16 H16F 56.3 . . ?
H16C C16 H16F 141.1 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 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 177.86(19) . . . . ?
C6 C1 C2 C3 -4.8(3) . . . . ?
O1 C1 C2 C7 -2.3(3) . . . . ?
C6 C1 C2 C7 175.07(17) . . . . ?
C7 C2 C3 C8 -4.8(3) . . . . ?
C1 C2 C3 C8 175.09(17) . . . . ?
C7 C2 C3 C4 179.13(17) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 O2 -175.96(17) . . . . ?
C8 C3 C4 O2 7.8(2) . . . . ?
C2 C3 C4 C5 5.7(2) . . . . ?
C8 C3 C4 C5 -170.54(15) . . . . ?
O2 C4 C5 C6 177.04(17) . . . . ?
C3 C4 C5 C6 -4.6(2) . . . . ?
O2 C4 C5 Cl1 -4.6(2) . . . . ?
C3 C4 C5 Cl1 173.74(12) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
Cl1 C5 C6 C1 -179.47(14) . . . . ?
C4 C5 C6 Cl2 178.23(13) . . . . ?
Cl1 C5 C6 Cl2 0.0(2) . . . . ?
O1 C1 C6 C5 -176.77(19) . . . . ?
C2 C1 C6 C5 5.9(3) . . . . ?
O1 C1 C6 Cl2 3.8(3) . . . . ?
C2 C1 C6 Cl2 -173.59(13) . . . . ?
C3 C2 C7 N1 -166(8) . . . . ?
C1 C2 C7 N1 14(8) . . . . ?
C2 C3 C8 N2 -65(6) . . . . ?
C4 C3 C8 N2 112(6) . . . . ?
C13 N3 C9 C10 -1.3(3) . . . . ?
C14 N3 C9 C10 173.9(2) . . . . ?
N3 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 2.2(4) . . . . ?
C10 C11 C12 C13 -2.2(4) . . . . ?
C9 N3 C13 C12 1.3(3) . . . . ?
C14 N3 C13 C12 -173.7(2) . . . . ?
C9 N3 C13 C16 -179.2(2) . . . . ?
C14 N3 C13 C16 5.8(3) . . . . ?
C11 C12 C13 N3 0.5(3) . . . . ?
C11 C12 C13 C16 -179.0(2) . . . . ?
C9 N3 C14 C15 -92.8(2) . . . . ?
C13 N3 C14 C15 82.4(3) . . . . ?


####################################################################### 
# 
# 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_ddq-py_1
_database_code_depnum_ccdc_archive 'CCDC 1584123'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2014-12-04T13:23:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C8 Cl2 N2 O2, C5 H6 N'
_chemical_formula_sum            'C13 H6 Cl2 N3 O2'
_chemical_formula_weight         307.11

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1343(7)
_cell_length_b                   15.8940(14)
_cell_length_c                   11.5190(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.678(8)
_cell_angle_gamma                90
_cell_volume                     1291.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2426
_cell_measurement_theta_min      3.8787
_cell_measurement_theta_max      75.8212

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.58
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    4.579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42342
_exptl_absorpt_correction_T_max  1

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'CCD, ω scans'
_diffrn_reflns_number            6048
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         75.9
_diffrn_reflns_theta_full        75.9
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_reflns_number_total             2625
_reflns_number_gt                2122
_reflns_threshold_expression     >2sigma(I)

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

_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)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1078P)²+0.0782P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1669
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.3

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
Cl1 Cl 0.01449(11) 0.80536(4) 0.11645(6) 0.0596(2) Uani 1 d . . .
Cl2 Cl -0.12993(12) 0.76236(5) -0.14968(7) 0.0651(3) Uani 1 d . . .
O1 O -0.3298(3) 0.90390(15) -0.27747(17) 0.0631(6) Uani 1 d . . .
O2 O -0.0646(3) 0.98067(12) 0.17581(16) 0.0520(4) Uani 1 d . . .
N1 N -0.5397(5) 1.1002(2) -0.2468(3) 0.0808(9) Uani 1 d . . .
N2 N -0.3430(4) 1.15478(17) 0.0926(3) 0.0664(7) Uani 1 d . . .
C1 C -0.2747(4) 0.92003(18) -0.1727(2) 0.0497(6) Uani 1 d . . .
C2 C -0.3167(3) 0.99909(17) -0.1185(2) 0.0475(6) Uani 1 d . . .
C3 C -0.2497(3) 1.01793(16) -0.0033(2) 0.0451(5) Uani 1 d . . .
C4 C -0.1331(3) 0.96069(16) 0.0729(2) 0.0444(5) Uani 1 d . . .
C5 C -0.1044(3) 0.87794(16) 0.0220(2) 0.0464(5) Uani 1 d . . .
C6 C -0.1690(4) 0.85912(16) -0.0919(2) 0.0482(6) Uani 1 d . . .
C7 C -0.4387(4) 1.0559(2) -0.1910(3) 0.0551(6) Uani 1 d . . .
C8 C -0.3002(4) 1.09515(17) 0.0494(2) 0.0508(6) Uani 1 d . . .
N3 N -0.9710(5) 0.90754(17) -0.6105(2) 0.0683(8) Uani 1 d . . .
H3 H -1.0107 0.9224 -0.6818 0.082 Uiso 1 calc R . .
C9 C -0.8131(6) 0.9421(2) -0.5558(3) 0.0727(9) Uani 1 d . . .
H9 H -0.7479 0.9821 -0.593 0.087 Uiso 1 calc R . .
C10 C -0.7479(6) 0.9172(3) -0.4426(4) 0.0864(12) Uani 1 d . . .
H10 H -0.6354 0.9391 -0.4028 0.104 Uiso 1 calc R . .
C11 C -0.8483(7) 0.8606(3) -0.3895(3) 0.0840(12) Uani 1 d . . .
H11 H -0.8061 0.8444 -0.3124 0.101 Uiso 1 calc R . .
C12 C -1.0117(7) 0.8271(3) -0.4489(4) 0.0842(11) Uani 1 d . . .
H12 H -1.0814 0.7883 -0.4127 0.101 Uiso 1 calc R . .
C13 C -1.0705(6) 0.8514(2) -0.5612(4) 0.0772(10) Uani 1 d . . .
H13 H -1.1804 0.8287 -0.6033 0.093 Uiso 1 calc R . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C5 1.719(3) . ?
Cl2 C6 1.715(3) . ?
O1 C1 1.238(3) . ?
O2 C4 1.253(3) . ?
N1 C7 1.135(4) . ?
N2 C8 1.134(4) . ?
C1 C2 1.454(4) . ?
C1 C6 1.470(4) . ?
C2 C3 1.374(4) . ?
C2 C7 1.432(4) . ?
C3 C4 1.438(3) . ?
C3 C8 1.439(4) . ?
C4 C5 1.467(4) . ?
C5 C6 1.356(4) . ?
N3 C13 1.321(5) . ?
N3 C9 1.324(5) . ?
N3 H3 0.86 . ?
C9 C10 1.375(6) . ?
C9 H9 0.93 . ?
C10 C11 1.352(7) . ?
C10 H10 0.93 . ?
C11 C12 1.367(7) . ?
C11 H11 0.93 . ?
C12 C13 1.355(6) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?

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 122.8(3) . . ?
O1 C1 C6 122.6(3) . . ?
C2 C1 C6 114.6(2) . . ?
C3 C2 C7 121.2(3) . . ?
C3 C2 C1 122.6(2) . . ?
C7 C2 C1 116.2(2) . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 C8 121.3(2) . . ?
C4 C3 C8 116.2(2) . . ?
O2 C4 C3 121.6(2) . . ?
O2 C4 C5 123.2(2) . . ?
C3 C4 C5 115.2(2) . . ?
C6 C5 C4 122.5(2) . . ?
C6 C5 Cl1 121.8(2) . . ?
C4 C5 Cl1 115.70(18) . . ?
C5 C6 C1 122.3(2) . . ?
C5 C6 Cl2 121.4(2) . . ?
C1 C6 Cl2 116.24(19) . . ?
N1 C7 C2 178.0(4) . . ?
N2 C8 C3 178.1(3) . . ?
C13 N3 C9 123.3(3) . . ?
C13 N3 H3 118.3 . . ?
C9 N3 H3 118.3 . . ?
N3 C9 C10 118.3(4) . . ?
N3 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.1(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N3 C13 C12 119.6(4) . . ?
N3 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?

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 -177.7(3) . . . . ?
C6 C1 C2 C3 5.0(4) . . . . ?
O1 C1 C2 C7 4.5(4) . . . . ?
C6 C1 C2 C7 -172.8(2) . . . . ?
C7 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C7 C2 C3 C8 0.4(4) . . . . ?
C1 C2 C3 C8 -177.3(2) . . . . ?
C2 C3 C4 O2 176.0(3) . . . . ?
C8 C3 C4 O2 -6.7(4) . . . . ?
C2 C3 C4 C5 -5.0(4) . . . . ?
C8 C3 C4 C5 172.2(2) . . . . ?
O2 C4 C5 C6 -175.6(3) . . . . ?
C3 C4 C5 C6 5.5(4) . . . . ?
O2 C4 C5 Cl1 5.2(3) . . . . ?
C3 C4 C5 Cl1 -173.74(18) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
Cl1 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 Cl2 178.92(19) . . . . ?
Cl1 C5 C6 Cl2 -1.9(3) . . . . ?
O1 C1 C6 C5 178.1(3) . . . . ?
C2 C1 C6 C5 -4.6(4) . . . . ?
O1 C1 C6 Cl2 -1.5(4) . . . . ?
C2 C1 C6 Cl2 175.82(19) . . . . ?
C3 C2 C7 N1 -76(11) . . . . ?
C1 C2 C7 N1 102(11) . . . . ?
C2 C3 C8 N2 109(9) . . . . ?
C4 C3 C8 N2 -68(10) . . . . ?
C13 N3 C9 C10 1.1(6) . . . . ?
N3 C9 C10 C11 -1.9(6) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?
C10 C11 C12 C13 0.1(7) . . . . ?
C9 N3 C13 C12 0.3(6) . . . . ?
C11 C12 C13 N3 -0.9(7) . . . . ?
####################################################################### 
# 
# 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_ddq_2pic_100k
_database_code_depnum_ccdc_archive 'CCDC 1823439'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2018-01-29T13:55:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_formula_sum            'C15 H10 Cl2 N3 O2'
_chemical_formula_moiety         'C8 Cl2 N2 O2, C7 H10 N'
_chemical_formula_weight         335.17

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.85120(10)
_cell_length_b                   11.09170(10)
_cell_length_c                   19.1460(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.3920(10)
_cell_angle_gamma                90
_cell_volume                     1450.66(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9148
_cell_measurement_theta_min      4.614
_cell_measurement_theta_max      76.346
_cell_measurement_temperature    100(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    4.126
_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  0.38497
_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            12662
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_theta_min         4.611
_diffrn_reflns_theta_max         76.436
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23

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

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

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

# REFINEMENT DATA

_reflns_number_total             3012
_reflns_number_gt                2926
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.118
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_number_reflns         3012
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0564P)²+2.2559P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.47
_refine_diff_density_rms         0.071
_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 0.44475(8) 0.22326(5) 0.06988(3) 0.02557(16) Uani d 1 . . Cl
Cl2 0.37745(8) 0.38345(5) 0.20233(3) 0.02873(16) Uani d 1 . . Cl
O1 0.2410(2) 0.62940(15) 0.16451(8) 0.0281(4) Uani d 1 . . O
O2 0.3667(2) 0.35539(14) -0.06279(7) 0.0222(3) Uani d 1 . . O
N1 0.0905(3) 0.8187(2) 0.02278(12) 0.0397(6) Uani d 1 . . N
N2 0.1475(3) 0.59964(17) -0.13992(12) 0.0280(4) Uani d 1 . . N
C1 0.2664(3) 0.5659(2) 0.11249(11) 0.0227(4) Uani d 1 . . C
C2 0.2202(3) 0.60787(19) 0.04096(11) 0.0214(4) Uani d 1 . . C
C3 0.2488(3) 0.5362(2) -0.01682(11) 0.0198(4) Uani d 1 . . C
C4 0.3309(3) 0.4162(2) -0.01089(11) 0.0199(4) Uani d 1 . . C
C5 0.3667(3) 0.37193(19) 0.06132(11) 0.0207(4) Uani d 1 . . C
C6 0.3361(3) 0.4415(2) 0.11816(11) 0.0219(4) Uani d 1 . . C
C7 0.1458(3) 0.7282(2) 0.03230(13) 0.0286(5) Uani d 1 . . C
C8 0.1914(3) 0.5746(2) -0.08753(13) 0.0253(5) Uani d 1 . . C
N3 0.7006(3) 0.07901(17) 0.21287(9) 0.0225(4) Uani d 1 . . N
C9 0.5260(3) 0.0218(2) 0.21401(11) 0.0223(4) Uani d 1 . . C
H9 0.443767 0.040303 0.248957 0.027 Uiso calc 1 . . H
C10 0.4686(4) -0.0631(2) 0.16445(12) 0.0297(5) Uani d 1 . . C
H10 0.349364 -0.102699 0.166008 0.036 Uiso calc 1 . . H
C11 0.5907(5) -0.0887(2) 0.11219(13) 0.0369(6) Uani d 1 . . C
H11 0.554136 -0.145338 0.077837 0.044 Uiso calc 1 . . H
C12 0.7663(4) -0.0296(2) 0.11158(13) 0.0363(6) Uani d 1 . . C
H12 0.848451 -0.046405 0.076336 0.044 Uiso calc 1 . . H
C13 0.8238(3) 0.0547(2) 0.16243(12) 0.0245(5) Uani d 1 . . C
C14 0.7567(4) 0.1699(2) 0.26772(12) 0.0295(5) Uani d 1 . . C
H14A 0.776599 0.2465 0.24608 0.044 Uiso calc 1 . . H
H14B 0.87556 0.145054 0.293555 0.044 Uiso calc 1 . . H
H14C 0.654252 0.176752 0.298996 0.044 Uiso calc 1 . . H
C15 1.0153(4) 0.1176(3) 0.16304(16) 0.0415(7) Uani d 1 . . C
H15A 1.086541 0.088008 0.125309 0.062 Uiso calc 1 . . H
H15B 1.089313 0.102732 0.206813 0.062 Uiso calc 1 . . H
H15C 0.993888 0.202687 0.157379 0.062 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 C5 . 1.737(2) ?
Cl2 C6 . 1.738(2) ?
O1 C1 . 1.243(3) ?
O2 C4 . 1.241(3) ?
N1 C7 . 1.083(4) ?
N2 C8 . 1.062(3) ?
C1 C2 . 1.458(3) ?
C1 C6 . 1.462(3) ?
C2 C3 . 1.388(3) ?
C2 C7 . 1.434(3) ?
C3 C8 . 1.445(3) ?
C3 C4 . 1.446(3) ?
C4 C5 . 1.470(3) ?
C5 C6 . 1.363(3) ?
N3 C9 . 1.356(3) ?
N3 C13 . 1.357(3) ?
N3 C14 . 1.485(3) ?
C9 C10 . 1.372(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.382(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.371(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.385(4) ?
C12 H12 . 0.93 ?
C13 C15 . 1.485(4) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 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 122.5(2) . . ?
O1 C1 C6 122.7(2) . . ?
C2 C1 C6 114.67(18) . . ?
C3 C2 C7 120.8(2) . . ?
C3 C2 C1 122.1(2) . . ?
C7 C2 C1 117.10(19) . . ?
C2 C3 C8 122.2(2) . . ?
C2 C3 C4 122.8(2) . . ?
C8 C3 C4 114.93(18) . . ?
O2 C4 C3 122.49(19) . . ?
O2 C4 C5 122.8(2) . . ?
C3 C4 C5 114.68(18) . . ?
C6 C5 C4 122.5(2) . . ?
C6 C5 Cl1 121.80(17) . . ?
C4 C5 Cl1 115.72(15) . . ?
C5 C6 C1 123.0(2) . . ?
C5 C6 Cl2 120.43(18) . . ?
C1 C6 Cl2 116.58(15) . . ?
N1 C7 C2 176.9(3) . . ?
N2 C8 C3 177.9(2) . . ?
C9 N3 C13 121.1(2) . . ?
C9 N3 C14 119.16(19) . . ?
C13 N3 C14 119.8(2) . . ?
N3 C9 C10 121.1(2) . . ?
N3 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 119.0(2) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N3 C13 C12 118.4(2) . . ?
N3 C13 C15 119.9(2) . . ?
C12 C13 C15 121.7(2) . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 -2.7(3) . . . . ?
O1 C1 C2 C7 1.0(3) . . . . ?
C6 C1 C2 C7 178.27(18) . . . . ?
C7 C2 C3 C8 -5.0(3) . . . . ?
C1 C2 C3 C8 175.92(19) . . . . ?
C7 C2 C3 C4 177.42(19) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C3 C4 O2 -175.68(19) . . . . ?
C8 C3 C4 O2 6.6(3) . . . . ?
C2 C3 C4 C5 4.8(3) . . . . ?
C8 C3 C4 C5 -172.91(17) . . . . ?
O2 C4 C5 C6 176.65(19) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
O2 C4 C5 Cl1 -5.0(3) . . . . ?
C3 C4 C5 Cl1 174.51(14) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
Cl1 C5 C6 C1 -178.60(15) . . . . ?
C4 C5 C6 Cl2 178.98(15) . . . . ?
Cl1 C5 C6 Cl2 0.8(3) . . . . ?
O1 C1 C6 C5 -179.1(2) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
O1 C1 C6 Cl2 1.5(3) . . . . ?
C2 C1 C6 Cl2 -175.74(15) . . . . ?
C13 N3 C9 C10 0.4(3) . . . . ?
C14 N3 C9 C10 -179.8(2) . . . . ?
N3 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C9 N3 C13 C12 0.5(3) . . . . ?
C14 N3 C13 C12 -179.3(2) . . . . ?
C9 N3 C13 C15 -179.2(2) . . . . ?
C14 N3 C13 C15 1.0(3) . . . . ?
C11 C12 C13 N3 -0.8(3) . . . . ?
C11 C12 C13 C15 178.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9 O1 0.93 2.38 3.291(3) 168 2_545 yes
C12 H12 N1 0.93 2.51 3.352(3) 150.6 1_645 yes
C15 H15B O1 0.96 2.66 3.586(4) 162.6 2_645 yes
C15 H15C N2 0.96 2.41 3.347(3) 165.1 3_665 yes
C9 H9 O1 0.93 2.38 3.291(3) 168 2_545 yes
C12 H12 N1 0.93 2.51 3.352(3) 150.6 1_645 yes
C15 H15B O1 0.96 2.66 3.586(4) 162.6 2_645 yes
C15 H15C N2 0.96 2.41 3.347(3) 165.1 3_665 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
####################################################################### 
# 
# 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_ddq_niac_2
_database_code_depnum_ccdc_archive 'CCDC 1584120'
_audit_update_record             
;
2017-11-08 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2017-11-08T12:37:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_formula_moiety         'C8 Cl2 N2 O2, C7 H9 N2 O'
_chemical_formula_sum            'C15 H9 Cl2 N4 O3'
_chemical_formula_weight         364.16

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

# 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                   6.8797(4)
_cell_length_b                   10.4684(6)
_cell_length_c                   11.0184(4)
_cell_angle_alpha                87.618(4)
_cell_angle_beta                 79.679(4)
_cell_angle_gamma                75.627(5)
_cell_volume                     756.26(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3296
_cell_measurement_theta_min      4.0748
_cell_measurement_theta_max      75.5984
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    4.117
_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  0.83336
_exptl_absorpt_correction_T_max  1

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

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_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            6225
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_theta_min         4.078
_diffrn_reflns_theta_max         75.785
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9

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

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

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

# REFINEMENT DATA

_reflns_number_total             3075
_reflns_number_gt                2838
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.137
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     224
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²+0.2032P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.055
_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, 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-2017/1 (Sheldrick, 2017)'
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.42387(9) 0.35733(7) 0.68695(5) 0.0656(2) Uani d 1 . . Cl
Cl2 0.28079(9) 0.20486(5) 0.92907(5) 0.05607(19) Uani d 1 . . Cl
O1 0.1232(3) 0.37883(14) 1.14266(13) 0.0486(3) Uani d 1 . . O
O2 0.3695(3) 0.6400(2) 0.73156(15) 0.0657(5) Uani d 1 . . O
N1 0.0834(3) 0.6899(2) 1.26253(18) 0.0550(5) Uani d 1 . . N
N2 0.2531(4) 0.8867(2) 0.9503(3) 0.0732(6) Uani d 1 . . N
C1 0.1868(3) 0.43705(19) 1.04911(17) 0.0396(4) Uani d 1 . . C
C2 0.1898(3) 0.57476(19) 1.05101(17) 0.0395(4) Uani d 1 . . C
C3 0.2491(3) 0.6423(2) 0.94566(18) 0.0428(4) Uani d 1 . . C
C4 0.3170(3) 0.5785(2) 0.82564(19) 0.0480(5) Uani d 1 . . C
C5 0.3275(3) 0.4372(2) 0.82584(18) 0.0454(4) Uani d 1 . . C
C6 0.2673(3) 0.3715(2) 0.92888(18) 0.0425(4) Uani d 1 . . C
C7 0.1300(3) 0.6384(2) 1.16938(19) 0.0430(4) Uani d 1 . . C
C8 0.2485(4) 0.7786(2) 0.9494(2) 0.0520(5) Uani d 1 . . C
O3 0.3698(3) 0.87633(18) 1.51282(17) 0.0614(4) Uani d 1 . . O
N3 -0.1565(3) 0.76420(17) 1.62944(15) 0.0434(4) Uani d 1 . . N
N4 0.2746(3) 1.0587(2) 1.6296(2) 0.0562(5) Uani d 1 . . N
H4A 0.381(4) 1.084(3) 1.600(3) 0.084 Uiso d 1 . . H
H4B 0.189(5) 1.112(3) 1.679(3) 0.084 Uiso d 1 . . H
C9 0.0172(3) 0.8020(2) 1.59253(17) 0.0428(4) Uani d 1 . . C
H9 0.117696 0.753396 1.532424 0.051 Uiso calc 1 . . H
C10 0.0487(3) 0.91229(19) 1.64269(18) 0.0421(4) Uani d 1 . . C
C11 -0.1004(4) 0.9806(2) 1.7346(2) 0.0530(5) Uani d 1 . . C
H11 -0.081612 1.054008 1.771251 0.064 Uiso calc 1 . . H
C12 -0.2778(4) 0.9389(2) 1.7718(2) 0.0545(5) Uani d 1 . . C
H12 -0.378937 0.984325 1.833406 0.065 Uiso calc 1 . . H
C13 -0.3034(3) 0.8305(2) 1.71720(19) 0.0474(5) Uani d 1 . . C
H13 -0.422992 0.802752 1.741101 0.057 Uiso calc 1 . . H
C14 -0.1828(4) 0.6438(3) 1.5765(2) 0.0608(6) Uani d 1 . . C
H14A -0.065843 0.607699 1.5153 0.091 Uiso calc 0.5 . . H
H14B -0.197171 0.580241 1.640736 0.091 Uiso calc 0.5 . . H
H14C -0.302618 0.665153 1.539141 0.091 Uiso calc 0.5 . . H
H14D -0.311245 0.627696 1.614818 0.091 Uiso calc 0.5 . . H
H14E -0.179917 0.655154 1.489382 0.091 Uiso calc 0.5 . . H
H14F -0.07447 0.570242 1.590976 0.091 Uiso calc 0.5 . . H
C15 0.2449(3) 0.9485(2) 1.59031(18) 0.0437(4) Uani d 1 . . 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
Cl1 C5 . 1.717(2) ?
Cl2 C6 . 1.724(2) ?
O1 C1 . 1.243(2) ?
O2 C4 . 1.243(3) ?
N1 C7 . 1.135(3) ?
N2 C8 . 1.141(3) ?
C1 C2 . 1.448(3) ?
C1 C6 . 1.468(3) ?
C2 C3 . 1.385(3) ?
C2 C7 . 1.435(3) ?
C3 C8 . 1.429(3) ?
C3 C4 . 1.453(3) ?
C4 C5 . 1.463(3) ?
C5 C6 . 1.357(3) ?
O3 C15 . 1.228(3) ?
N3 C13 . 1.340(3) ?
N3 C9 . 1.341(3) ?
N3 C14 . 1.474(3) ?
N4 C15 . 1.323(3) ?
N4 H4A . 0.846(19) ?
N4 H4B . 0.837(18) ?
C9 C10 . 1.380(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.383(3) ?
C10 C15 . 1.502(3) ?
C11 C12 . 1.385(3) ?
C11 H11 . 0.93 ?
C12 C13 . 1.369(3) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C14 H14D . 0.96 ?
C14 H14E . 0.96 ?
C14 H14F . 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 122.33(17) . . ?
O1 C1 C6 122.80(18) . . ?
C2 C1 C6 114.86(17) . . ?
C3 C2 C7 121.17(18) . . ?
C3 C2 C1 122.61(17) . . ?
C7 C2 C1 116.22(17) . . ?
C2 C3 C8 121.67(19) . . ?
C2 C3 C4 122.06(19) . . ?
C8 C3 C4 116.27(18) . . ?
O2 C4 C3 121.6(2) . . ?
O2 C4 C5 123.3(2) . . ?
C3 C4 C5 115.03(18) . . ?
C6 C5 C4 122.75(18) . . ?
C6 C5 Cl1 121.37(18) . . ?
C4 C5 Cl1 115.88(15) . . ?
C5 C6 C1 122.46(19) . . ?
C5 C6 Cl2 122.68(16) . . ?
C1 C6 Cl2 114.87(15) . . ?
N1 C7 C2 179.3(2) . . ?
N2 C8 C3 178.1(3) . . ?
C13 N3 C9 121.37(18) . . ?
C13 N3 C14 119.17(19) . . ?
C9 N3 C14 119.40(19) . . ?
C15 N4 H4A 121(2) . . ?
C15 N4 H4B 125(3) . . ?
H4A N4 H4B 115(3) . . ?
N3 C9 C10 120.77(19) . . ?
N3 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 C15 116.06(18) . . ?
C11 C10 C15 125.46(19) . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 119.6(2) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N3 C13 C12 120.1(2) . . ?
N3 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
O3 C15 N4 122.7(2) . . ?
O3 C15 C10 119.32(19) . . ?
N4 C15 C10 117.98(18) . . ?

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 -176.05(18) . . . . ?
C6 C1 C2 C3 4.8(3) . . . . ?
O1 C1 C2 C7 4.7(3) . . . . ?
C6 C1 C2 C7 -174.43(16) . . . . ?
C7 C2 C3 C8 -1.6(3) . . . . ?
C1 C2 C3 C8 179.22(18) . . . . ?
C7 C2 C3 C4 177.79(17) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 O2 179.9(2) . . . . ?
C8 C3 C4 O2 -0.7(3) . . . . ?
C2 C3 C4 C5 -2.9(3) . . . . ?
C8 C3 C4 C5 176.55(18) . . . . ?
O2 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C5 C6 3.6(3) . . . . ?
O2 C4 C5 Cl1 1.5(3) . . . . ?
C3 C4 C5 Cl1 -175.72(14) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
Cl1 C5 C6 C1 179.18(14) . . . . ?
C4 C5 C6 Cl2 -179.69(15) . . . . ?
Cl1 C5 C6 Cl2 -0.4(2) . . . . ?
O1 C1 C6 C5 176.79(19) . . . . ?
C2 C1 C6 C5 -4.1(3) . . . . ?
O1 C1 C6 Cl2 -3.6(2) . . . . ?
C2 C1 C6 Cl2 175.55(13) . . . . ?
C13 N3 C9 C10 -1.1(3) . . . . ?
C14 N3 C9 C10 -178.28(19) . . . . ?
N3 C9 C10 C11 2.0(3) . . . . ?
N3 C9 C10 C15 -177.42(17) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C15 C10 C11 C12 177.9(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C9 N3 C13 C12 -0.3(3) . . . . ?
C14 N3 C13 C12 176.9(2) . . . . ?
C11 C12 C13 N3 0.8(3) . . . . ?
C9 C10 C15 O3 -4.1(3) . . . . ?
C11 C10 C15 O3 176.5(2) . . . . ?
C9 C10 C15 N4 175.32(19) . . . . ?
C11 C10 C15 N4 -4.0(3) . . . . ?



# 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
####################################################################### 
# 
# 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_ddq_kinoksalin_100k
_database_code_depnum_ccdc_archive 'CCDC 1584118'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2016-12-22T15:28:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H9 Cl2 N4 O2'
_chemical_formula_sum            'C17 H9 Cl2 N4 O2'
_chemical_formula_weight         372.18

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

# 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                   6.5095(4)
_cell_length_b                   10.0244(6)
_cell_length_c                   12.1968(9)
_cell_angle_alpha                96.753(5)
_cell_angle_beta                 98.883(6)
_cell_angle_gamma                104.199(5)
_cell_volume                     752.21(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1940
_cell_measurement_theta_min      3.7142
_cell_measurement_theta_max      75.8319
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    4.072
_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  0.6417
_exptl_absorpt_correction_T_max  1

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(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            6590
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_theta_min         3.72
_diffrn_reflns_theta_max         76.02
_diffrn_reflns_theta_full        76.02
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15

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

# 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             3083
_reflns_number_gt                2716
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.1478
_refine_ls_wR_factor_ref         0.3196
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.14
_refine_ls_number_reflns         3083
_refine_ls_number_parameters     296
_refine_ls_number_restraints     176
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0001P)²+14.4240P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.748
_refine_diff_density_min         -1.155
_refine_diff_density_rms         0.137
_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, 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 0.1887(6) 0.6149(3) 0.8222(4) 0.0231(8) Uani d PU 0.722(9) A 1 Cl
Cl2A 0.2523(5) 0.8365(4) 1.0391(2) 0.0242(8) Uani d PU 0.722(9) A 1 Cl
O1A 0.3425(16) 0.7279(11) 1.2478(8) 0.025(2) Uani d PU 0.722(9) A 1 O
O2A 0.2431(17) 0.3477(10) 0.8744(8) 0.023(2) Uani d PU 0.722(9) A 1 O
N1A 0.386(2) 0.4285(16) 1.3637(12) 0.032(4) Uani d PDU 0.722(9) A 1 N
N2A 0.291(3) 0.1478(16) 1.0988(15) 0.040(5) Uani d PDU 0.722(9) A 1 N
C1A 0.320(2) 0.6444(14) 1.1600(12) 0.020(3) Uani d PU 0.722(9) A 1 C
C2A 0.327(2) 0.4998(12) 1.1663(10) 0.022(2) Uani d PDU 0.722(9) A 1 C
C3A 0.300(2) 0.4001(13) 1.0715(11) 0.022(3) Uiso d PDU 0.722(9) A 1 C
C4A 0.264(2) 0.4351(13) 0.9579(12) 0.017(2) Uani d PU 0.722(9) A 1 C
C5A 0.246(2) 0.5751(14) 0.9543(12) 0.019(3) Uiso d PU 0.722(9) A 1 C
C6A 0.2741(17) 0.6712(12) 1.0484(9) 0.014(2) Uiso d PU 0.722(9) A 1 C
C7A 0.356(2) 0.4611(14) 1.2762(10) 0.023(3) Uani d PDU 0.722(9) A 1 C
C8A 0.2945(19) 0.2585(14) 1.0840(10) 0.021(3) Uiso d PDU 0.722(9) A 1 C
Cl1B 0.3641(16) 0.4175(11) 1.3225(12) 0.032(3) Uani d PDU 0.278(9) A 2 Cl
Cl2B 0.2942(15) 0.1966(14) 1.1055(8) 0.031(2) Uani d PDU 0.278(9) A 2 Cl
O1B 0.264(4) 0.317(2) 0.896(2) 0.009(5) Uani d PU 0.278(9) A 2 O
O2B 0.359(4) 0.696(3) 1.274(2) 0.019(6) Uani d PU 0.278(9) A 2 O
N1B 0.158(5) 0.602(4) 0.782(2) 0.022(9) Uani d PDU 0.278(9) A 2 N
N2B 0.244(5) 0.885(3) 1.060(3) 0.025(8) Uani d PDU 0.278(9) A 2 N
C1B 0.284(6) 0.408(4) 0.984(2) 0.012(8) Uiso d PDU 0.278(9) A 2 C
C2B 0.274(5) 0.550(3) 0.982(2) 0.018(6) Uani d PDU 0.278(9) A 2 C
C3B 0.291(4) 0.639(2) 1.080(2) 0.016(5) Uiso d PDU 0.278(9) A 2 C
C4B 0.336(7) 0.614(4) 1.183(4) 0.02 Uiso d PU 0.278(9) A 2 C
C5B 0.340(6) 0.463(3) 1.1913(17) 0.02 Uiso d PDU 0.278(9) A 2 C
C6B 0.308(5) 0.369(2) 1.096(2) 0.020(7) Uiso d PDU 0.278(9) A 2 C
C7B 0.198(4) 0.575(3) 0.870(2) 0.014(5) Uiso d PDU 0.278(9) A 2 C
C8B 0.258(4) 0.774(2) 1.069(2) 0.011(5) Uiso d PDU 0.278(9) A 2 C
N3 0.0622(13) 0.9732(8) 0.7053(6) 0.0318(17) Uani d . 1 . . N
N4 -0.2933(13) 0.9150(9) 0.5315(7) 0.0339(18) Uani d . 1 . . N
C9 -0.0803(18) 1.0449(11) 0.7067(9) 0.042(2) Uani d . 1 . . C
H9 -0.0614 1.1168 0.7661 0.05 Uiso calc R 1 . . H
C10 -0.2620(17) 1.0149(10) 0.6196(9) 0.037(2) Uani d . 1 . . C
H10 -0.3628 1.0661 0.6235 0.045 Uiso calc R 1 . . H
C11 -0.1419(15) 0.8413(9) 0.5309(8) 0.0296(19) Uani d . 1 . . C
C12 -0.1698(17) 0.7370(10) 0.4350(8) 0.036(2) Uani d . 1 . . C
H12 -0.2891 0.7182 0.3771 0.043 Uiso calc R 1 . . H
C13 -0.0166(18) 0.6660(10) 0.4309(8) 0.038(2) Uani d . 1 . . C
H13 -0.0343 0.597 0.3695 0.046 Uiso calc R 1 . . H
C14 0.1660(17) 0.6934(10) 0.5155(9) 0.038(2) Uani d . 1 . . C
H14 0.2684 0.6442 0.5086 0.046 Uiso calc R 1 . . H
C15 0.1971(15) 0.7939(10) 0.6107(9) 0.034(2) Uani d . 1 . . C
H15 0.3166 0.8112 0.6682 0.04 Uiso calc R 1 . . H
C16 0.0419(15) 0.8670(9) 0.6157(7) 0.0277(18) Uani d . 1 . . C
C17 0.2517(18) 1.0074(12) 0.7949(8) 0.044(3) Uani d . 1 . . C
H17A 0.3388 0.9449 0.781 0.066 Uiso calc R 1 . . H
H17B 0.2068 0.9982 0.8656 0.066 Uiso calc R 1 . . H
H17C 0.3343 1.1016 0.7971 0.066 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 C5A . 1.713(14) ?
Cl2A C6A . 1.712(12) ?
O1A C1A . 1.244(16) ?
O2A C4A . 1.230(15) ?
N1A C7A . 1.153(14) ?
N2A C8A . 1.139(14) ?
C1A C6A . 1.420(16) ?
C1A C2A . 1.471(16) ?
C2A C3A . 1.396(16) ?
C2A C7A . 1.437(13) ?
C3A C8A . 1.438(14) ?
C3A C4A . 1.467(18) ?
C4A C5A . 1.442(17) ?
C5A C6A . 1.367(16) ?
Cl1B C5B . 1.711(18) ?
Cl2B C6B . 1.728(18) ?
O1B C1B . 1.30(4) ?
O2B C4B . 1.27(5) ?
N1B C7B . 1.152(19) ?
N2B C8B . 1.151(19) ?
C1B C2B . 1.44(4) ?
C1B C6B . 1.460(18) ?
C2B C3B . 1.374(18) ?
C2B C7B . 1.449(19) ?
C3B C4B . 1.32(4) ?
C3B C8B . 1.445(18) ?
C4B C5B . 1.53(5) ?
C5B C6B . 1.361(18) ?
N3 C9 . 1.306(13) ?
N3 C16 . 1.399(11) ?
N3 C17 . 1.457(13) ?
N4 C10 . 1.333(12) ?
N4 C11 . 1.370(12) ?
C9 C10 . 1.408(16) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
C11 C16 . 1.404(13) ?
C11 C12 . 1.431(13) ?
C12 C13 . 1.363(15) ?
C12 H12 . 0.93 ?
C13 C14 . 1.396(15) ?
C13 H13 . 0.93 ?
C14 C15 . 1.398(14) ?
C14 H14 . 0.93 ?
C15 C16 . 1.390(13) ?
C15 H15 . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 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 C6A 126.2(11) . . ?
O1A C1A C2A 120.0(12) . . ?
C6A C1A C2A 113.7(11) . . ?
C3A C2A C7A 119.6(11) . . ?
C3A C2A C1A 123.2(11) . . ?
C7A C2A C1A 117.2(11) . . ?
C2A C3A C8A 120.0(12) . . ?
C2A C3A C4A 121.0(11) . . ?
C8A C3A C4A 118.9(10) . . ?
O2A C4A C5A 124.4(14) . . ?
O2A C4A C3A 121.1(12) . . ?
C5A C4A C3A 114.5(11) . . ?
C6A C5A C4A 123.3(13) . . ?
C6A C5A Cl1A 121.5(10) . . ?
C4A C5A Cl1A 115.2(10) . . ?
C5A C6A C1A 124.2(11) . . ?
C5A C6A Cl2A 121.4(10) . . ?
C1A C6A Cl2A 114.5(8) . . ?
N1A C7A C2A 177.7(15) . . ?
N2A C8A C3A 177.0(15) . . ?
O1B C1B C2B 125(2) . . ?
O1B C1B C6B 121(3) . . ?
C2B C1B C6B 115(3) . . ?
C3B C2B C1B 121(3) . . ?
C3B C2B C7B 125(3) . . ?
C1B C2B C7B 113(2) . . ?
C4B C3B C2B 127(3) . . ?
C4B C3B C8B 116(3) . . ?
C2B C3B C8B 117(3) . . ?
O2B C4B C3B 128(4) . . ?
O2B C4B C5B 117(3) . . ?
C3B C4B C5B 115(3) . . ?
C6B C5B C4B 120(2) . . ?
C6B C5B Cl1B 122(2) . . ?
C4B C5B Cl1B 117(2) . . ?
C5B C6B C1B 122(2) . . ?
C5B C6B Cl2B 120(2) . . ?
C1B C6B Cl2B 118(2) . . ?
N1B C7B C2B 174(3) . . ?
N2B C8B C3B 175(3) . . ?
C9 N3 C16 121.0(9) . . ?
C9 N3 C17 120.2(9) . . ?
C16 N3 C17 118.6(8) . . ?
C10 N4 C11 116.7(9) . . ?
N3 C9 C10 120.9(9) . . ?
N3 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N4 C10 C9 121.7(9) . . ?
N4 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
N4 C11 C16 123.8(8) . . ?
N4 C11 C12 117.2(9) . . ?
C16 C11 C12 118.9(8) . . ?
C13 C12 C11 118.2(9) . . ?
C13 C12 H12 120.9 . . ?
C11 C12 H12 120.9 . . ?
C12 C13 C14 122.3(9) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C15 C14 C13 120.9(9) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 117.2(9) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 N3 121.7(9) . . ?
C15 C16 C11 122.5(8) . . ?
N3 C16 C11 115.8(8) . . ?
N3 C17 H17A 109.5 . . ?
N3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 179.1(12) . . . . ?
C6A C1A C2A C3A 2.7(18) . . . . ?
O1A C1A C2A C7A 1.0(18) . . . . ?
C6A C1A C2A C7A -175.4(11) . . . . ?
C7A C2A C3A C8A 2.2(18) . . . . ?
C1A C2A C3A C8A -175.8(11) . . . . ?
C7A C2A C3A C4A 178.4(11) . . . . ?
C1A C2A C3A C4A 0.3(19) . . . . ?
C2A C3A C4A O2A 179.0(12) . . . . ?
C8A C3A C4A O2A -4.8(18) . . . . ?
C2A C3A C4A C5A -3.5(17) . . . . ?
C8A C3A C4A C5A 172.6(11) . . . . ?
O2A C4A C5A C6A -178.7(12) . . . . ?
C3A C4A C5A C6A 4.0(18) . . . . ?
O2A C4A C5A Cl1A 0.8(18) . . . . ?
C3A C4A C5A Cl1A -176.5(9) . . . . ?
C4A C5A C6A C1A -1(2) . . . . ?
Cl1A C5A C6A C1A 179.5(10) . . . . ?
C4A C5A C6A Cl2A 179.7(10) . . . . ?
Cl1A C5A C6A Cl2A 0.2(16) . . . . ?
O1A C1A C6A C5A -178.5(13) . . . . ?
C2A C1A C6A C5A -2.3(18) . . . . ?
O1A C1A C6A Cl2A 0.8(18) . . . . ?
C2A C1A C6A Cl2A 177.0(9) . . . . ?
C3A C2A C7A N1A 6E1(4) . . . . ?
C1A C2A C7A N1A -13E1(4) . . . . ?
C2A C3A C8A N2A 0E1(3) . . . . ?
C4A C3A C8A N2A -17E1(3) . . . . ?
O1B C1B C2B C3B 178(3) . . . . ?
C6B C1B C2B C3B 1(5) . . . . ?
O1B C1B C2B C7B 11(5) . . . . ?
C6B C1B C2B C7B -166(3) . . . . ?
C1B C2B C3B C4B 6(5) . . . . ?
C7B C2B C3B C4B 172(4) . . . . ?
C1B C2B C3B C8B -174(3) . . . . ?
C7B C2B C3B C8B -8(4) . . . . ?
C2B C3B C4B O2B 178(4) . . . . ?
C8B C3B C4B O2B -2(6) . . . . ?
C2B C3B C4B C5B -8(6) . . . . ?
C8B C3B C4B C5B 172(3) . . . . ?
O2B C4B C5B C6B 178(3) . . . . ?
C3B C4B C5B C6B 3(5) . . . . ?
O2B C4B C5B Cl1B 2(5) . . . . ?
C3B C4B C5B Cl1B -172(3) . . . . ?
C4B C5B C6B C1B 4(5) . . . . ?
Cl1B C5B C6B C1B 179(3) . . . . ?
C4B C5B C6B Cl2B -176(3) . . . . ?
Cl1B C5B C6B Cl2B -1(4) . . . . ?
O1B C1B C6B C5B 177(3) . . . . ?
C2B C1B C6B C5B -6(5) . . . . ?
O1B C1B C6B Cl2B -4(4) . . . . ?
C2B C1B C6B Cl2B 174(2) . . . . ?
C3B C2B C7B N1B 8E1(3) . . . . ?
C1B C2B C7B N1B -11E1(3) . . . . ?
C4B C3B C8B N2B 10E1(4) . . . . ?
C2B C3B C8B N2B -8E1(4) . . . . ?
C16 N3 C9 C10 1.7(14) . . . . ?
C17 N3 C9 C10 178.8(9) . . . . ?
C11 N4 C10 C9 1.1(14) . . . . ?
N3 C9 C10 N4 -1.5(16) . . . . ?
C10 N4 C11 C16 -1.1(13) . . . . ?
C10 N4 C11 C12 -177.9(9) . . . . ?
N4 C11 C12 C13 177.6(9) . . . . ?
C16 C11 C12 C13 0.7(13) . . . . ?
C11 C12 C13 C14 -1.1(15) . . . . ?
C12 C13 C14 C15 1.6(16) . . . . ?
C13 C14 C15 C16 -1.5(14) . . . . ?
C14 C15 C16 N3 -177.6(8) . . . . ?
C14 C15 C16 C11 1.2(14) . . . . ?
C9 N3 C16 C15 177.2(9) . . . . ?
C17 N3 C16 C15 0.1(13) . . . . ?
C9 N3 C16 C11 -1.6(12) . . . . ?
C17 N3 C16 C11 -178.7(8) . . . . ?
N4 C11 C16 C15 -177.5(9) . . . . ?
C12 C11 C16 C15 -0.7(13) . . . . ?
N4 C11 C16 N3 1.3(13) . . . . ?
C12 C11 C16 N3 178.0(8) . . . . ?


####################################################################### 
# 
# 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_ddq_4cn_2
_database_code_depnum_ccdc_archive 'CCDC 1584116'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2016-12-02T11:27:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H7 Cl2 N2 O2'
_chemical_formula_sum            'C15 H7 Cl2 N4 O2'
_chemical_formula_weight         346.15

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.87171(7)
_cell_length_b                   10.10504(9)
_cell_length_c                   20.5512(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.6882(9)
_cell_angle_gamma                90
_cell_volume                     1422.28(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8636
_cell_measurement_theta_min      4.3135
_cell_measurement_theta_max      75.7513
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    4.256
_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  0.60602
_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            13063
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_theta_min         4.32
_diffrn_reflns_theta_max         75.94
_diffrn_reflns_theta_full        75.94
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

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

# 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             2956
_reflns_number_gt                2810
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0815
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.2450P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.25
_refine_diff_density_rms         0.046
_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, 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 0.20439(5) 0.11333(3) -0.007185(16) 0.04093(11) Uani d . 1 . . Cl
Cl2 0.11639(5) 0.28120(3) 0.116909(15) 0.04083(11) Uani d . 1 . . Cl
O1 0.13580(14) 0.56636(9) 0.09443(4) 0.0389(2) Uani d . 1 . . O
O2 0.28913(17) 0.27814(9) -0.11789(5) 0.0444(2) Uani d . 1 . . O
N1 0.29897(19) 0.81216(12) -0.00661(7) 0.0479(3) Uani d . 1 . . N
N2 0.4169(2) 0.59815(13) -0.16652(6) 0.0478(3) Uani d . 1 . . N
C1 0.18067(16) 0.49996(12) 0.04706(6) 0.0303(2) Uani d . 1 . . C
C2 0.24725(17) 0.56006(12) -0.01135(6) 0.0295(2) Uani d . 1 . . C
C3 0.28831(16) 0.48665(12) -0.06559(6) 0.0300(2) Uani d . 1 . . C
C4 0.26358(17) 0.34369(12) -0.06842(6) 0.0316(2) Uani d . 1 . . C
C5 0.21249(17) 0.28291(12) -0.00738(6) 0.0309(2) Uani d . 1 . . C
C6 0.17397(17) 0.35465(12) 0.04576(6) 0.0309(2) Uani d . 1 . . C
C7 0.27593(18) 0.70041(12) -0.00893(6) 0.0335(3) Uani d . 1 . . C
C8 0.35889(18) 0.54933(13) -0.12158(6) 0.0340(3) Uani d . 1 . . C
N3 0.32053(18) 0.95298(11) 0.18318(6) 0.0422(3) Uani d . 1 . . N
N4 0.9877(2) 1.20220(16) 0.24799(7) 0.0577(4) Uani d . 1 . . N
C9 0.3532(2) 0.99901(14) 0.24440(7) 0.0419(3) Uani d . 1 . . C
H9 0.2613 0.9844 0.2744 0.05 Uiso calc R 1 . . H
C10 0.5213(2) 1.06759(14) 0.26303(6) 0.0388(3) Uani d . 1 . . C
H10 0.5442 1.0996 0.3054 0.047 Uiso calc R 1 . . H
C11 0.6562(2) 1.08812(13) 0.21735(6) 0.0380(3) Uani d . 1 . . C
C12 0.6188(2) 1.04075(16) 0.15432(7) 0.0465(3) Uani d . 1 . . C
H12 0.7074 1.0554 0.1232 0.056 Uiso calc R 1 . . H
C13 0.4505(2) 0.97238(15) 0.13854(7) 0.0474(3) Uani d . 1 . . C
H13 0.4253 0.9388 0.0966 0.057 Uiso calc R 1 . . H
C14 0.1418(3) 0.8759(2) 0.16449(11) 0.0678(5) Uani d . 1 . . C
H14A 0.0633 0.8708 0.201 0.102 Uiso calc R 1 . . H
H14B 0.1771 0.7882 0.1518 0.102 Uiso calc R 1 . . H
H14C 0.0689 0.9185 0.1286 0.102 Uiso calc R 1 . . H
C15 0.8387(2) 1.15469(15) 0.23544(7) 0.0449(3) Uani d . 1 . . 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
Cl1 C5 . 1.7145(12) ?
Cl2 C6 . 1.7147(12) ?
O1 C1 . 1.2417(15) ?
O2 C4 . 1.2379(15) ?
N1 C7 . 1.1408(18) ?
N2 C8 . 1.1471(18) ?
C1 C2 . 1.4522(16) ?
C1 C6 . 1.4693(17) ?
C2 C3 . 1.3871(17) ?
C2 C7 . 1.4322(17) ?
C3 C8 . 1.4323(17) ?
C3 C4 . 1.4552(17) ?
C4 C5 . 1.4649(17) ?
C5 C6 . 1.3547(17) ?
N3 C9 . 1.3430(18) ?
N3 C13 . 1.346(2) ?
N3 C14 . 1.479(2) ?
N4 C15 . 1.141(2) ?
C9 C10 . 1.374(2) ?
C9 H9 . 0.93 ?
C10 C11 . 1.388(2) ?
C10 H10 . 0.93 ?
C11 C12 . 1.385(2) ?
C11 C15 . 1.445(2) ?
C12 C13 . 1.363(2) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 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 122.49(11) . . ?
O1 C1 C6 123.02(11) . . ?
C2 C1 C6 114.48(10) . . ?
C3 C2 C7 121.40(11) . . ?
C3 C2 C1 122.63(11) . . ?
C7 C2 C1 115.92(11) . . ?
C2 C3 C8 120.91(11) . . ?
C2 C3 C4 122.15(11) . . ?
C8 C3 C4 116.94(10) . . ?
O2 C4 C3 122.68(11) . . ?
O2 C4 C5 122.61(11) . . ?
C3 C4 C5 114.68(10) . . ?
C6 C5 C4 122.83(11) . . ?
C6 C5 Cl1 121.63(9) . . ?
C4 C5 Cl1 115.54(9) . . ?
C5 C6 C1 122.80(11) . . ?
C5 C6 Cl2 121.98(10) . . ?
C1 C6 Cl2 115.22(9) . . ?
N1 C7 C2 179.60(15) . . ?
N2 C8 C3 179.12(15) . . ?
C9 N3 C13 121.24(13) . . ?
C9 N3 C14 119.83(15) . . ?
C13 N3 C14 118.90(14) . . ?
N3 C9 C10 120.53(13) . . ?
N3 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 118.65(13) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 119.87(13) . . ?
C12 C11 C15 119.48(13) . . ?
C10 C11 C15 120.61(12) . . ?
C13 C12 C11 119.10(14) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N3 C13 C12 120.60(13) . . ?
N3 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 C11 176.38(18) . . ?

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 -176.75(11) . . . . ?
C6 C1 C2 C3 4.17(16) . . . . ?
O1 C1 C2 C7 5.64(17) . . . . ?
C6 C1 C2 C7 -173.44(10) . . . . ?
C7 C2 C3 C8 -0.77(18) . . . . ?
C1 C2 C3 C8 -178.24(11) . . . . ?
C7 C2 C3 C4 178.81(11) . . . . ?
C1 C2 C3 C4 1.33(18) . . . . ?
C2 C3 C4 O2 175.79(12) . . . . ?
C8 C3 C4 O2 -4.61(18) . . . . ?
C2 C3 C4 C5 -6.18(16) . . . . ?
C8 C3 C4 C5 173.41(10) . . . . ?
O2 C4 C5 C6 -176.30(12) . . . . ?
C3 C4 C5 C6 5.68(17) . . . . ?
O2 C4 C5 Cl1 3.73(17) . . . . ?
C3 C4 C5 Cl1 -174.29(8) . . . . ?
C4 C5 C6 C1 -0.25(18) . . . . ?
Cl1 C5 C6 C1 179.72(9) . . . . ?
C4 C5 C6 Cl2 -179.46(9) . . . . ?
Cl1 C5 C6 Cl2 0.50(15) . . . . ?
O1 C1 C6 C5 176.19(11) . . . . ?
C2 C1 C6 C5 -4.73(17) . . . . ?
O1 C1 C6 Cl2 -4.54(16) . . . . ?
C2 C1 C6 Cl2 174.54(8) . . . . ?
C3 C2 C7 N1 -15E1(4) . . . . ?
C1 C2 C7 N1 3E1(4) . . . . ?
C2 C3 C8 N2 143(10) . . . . ?
C4 C3 C8 N2 -37(10) . . . . ?
C13 N3 C9 C10 0.1(2) . . . . ?
C14 N3 C9 C10 178.13(14) . . . . ?
N3 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C9 C10 C11 C15 -177.33(13) . . . . ?
C10 C11 C12 C13 -1.1(2) . . . . ?
C15 C11 C12 C13 176.81(14) . . . . ?
C9 N3 C13 C12 -0.6(2) . . . . ?
C14 N3 C13 C12 -178.72(15) . . . . ?
C11 C12 C13 N3 1.1(2) . . . . ?
C12 C11 C15 N4 -43(3) . . . . ?
C10 C11 C15 N4 135(3) . . . . ?


####################################################################### 
# 
# 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_ddq_nik_100k
_database_code_depnum_ccdc_archive 'CCDC 1584121'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2017-02-17T11:18:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H10 Cl2 N3 O4'
_chemical_formula_sum            'C16 H10 Cl2 N3 O4'
_chemical_formula_weight         379.17

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 1 a 1'
_symmetry_space_group_name_Hall  'I -2ya'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   19.9026(2)
_cell_length_b                   6.76710(10)
_cell_length_c                   23.9113(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.5520(10)
_cell_angle_gamma                90
_cell_volume                     3117.13(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11788
_cell_measurement_theta_min      3.3306
_cell_measurement_theta_max      75.772
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544
_exptl_absorpt_coefficient_mu    4.019
_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  0.41427
_exptl_absorpt_correction_T_max  1

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      100(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            13963
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         75.95
_diffrn_reflns_theta_full        75.95
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       29

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

# 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             4433
_reflns_number_gt                4396
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.087
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_restrained_S_all      0.898
_refine_ls_number_reflns         4433
_refine_ls_number_parameters     452
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0817P)²+0.7263P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.269(13)
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 0.88504(2) 0.85820(7) 0.60365(2) 0.01441(12) Uani d . 1 . . Cl
Cl2A 0.76373(3) 0.74422(8) 0.49376(2) 0.01595(12) Uani d . 1 . . Cl
O1A 0.62641(9) 0.8218(3) 0.51155(8) 0.0204(3) Uani d . 1 . . O
O2A 0.83309(8) 0.9679(2) 0.70357(7) 0.0154(3) Uani d . 1 . . O
N1A 0.53406(11) 1.0400(4) 0.60212(11) 0.0242(5) Uani d . 1 . . N
N2A 0.68301(12) 1.1445(3) 0.74422(10) 0.0222(5) Uani d . 1 . . N
C1A 0.67380(12) 0.8586(3) 0.55512(11) 0.0150(4) Uani d . 1 . . C
C2A 0.66113(12) 0.9443(3) 0.60681(10) 0.0133(4) Uani d . 1 . . C
C3A 0.71381(12) 0.9810(3) 0.65614(10) 0.0133(4) Uani d . 1 . . C
C4A 0.78584(12) 0.9411(3) 0.65900(10) 0.0123(4) Uani d . 1 . . C
C5A 0.79897(12) 0.8713(3) 0.60439(10) 0.0122(4) Uani d . 1 . . C
C6A 0.74736(12) 0.8289(3) 0.55669(10) 0.0131(4) Uani d . 1 . . C
C7A 0.59086(13) 0.9958(4) 0.60488(10) 0.0175(4) Uani d . 1 . . C
C8A 0.69837(12) 1.0722(3) 0.70576(11) 0.0152(4) Uani d . 1 . . C
Cl1B 0.94918(3) 0.43985(8) 0.71234(3) 0.01840(13) Uani d . 1 . . Cl
Cl2B 0.82039(3) 0.36998(7) 0.60475(2) 0.01716(13) Uani d . 1 . . Cl
O1B 0.69005(8) 0.5088(3) 0.62581(7) 0.0168(3) Uani d . 1 . . O
O2B 0.91063(9) 0.6401(3) 0.80805(8) 0.0197(4) Uani d . 1 . . O
N1B 0.60610(11) 0.6657(3) 0.72824(10) 0.0203(4) Uani d . 1 . . N
N2B 0.77224(12) 0.8036(4) 0.86345(10) 0.0235(4) Uani d . 1 . . N
C1B 0.74062(12) 0.5346(3) 0.66797(10) 0.0130(4) Uani d . 1 . . C
C2B 0.73315(12) 0.6164(3) 0.72227(10) 0.0125(4) Uani d . 1 . . C
C3B 0.78929(12) 0.6534(3) 0.76847(10) 0.0141(4) Uani d . 1 . . C
C4B 0.85996(12) 0.6078(3) 0.76691(10) 0.0152(5) Uani d . 1 . . C
C5B 0.86655(11) 0.5123(3) 0.71333(10) 0.0143(4) Uani d . 1 . . C
C6B 0.81157(12) 0.4810(3) 0.66717(10) 0.0139(4) Uani d . 1 . . C
C7B 0.66293(13) 0.6450(3) 0.72608(10) 0.0143(4) Uani d . 1 . . C
C8B 0.77988(12) 0.7375(3) 0.82119(11) 0.0167(5) Uani d . 1 . . C
O3A 0.84294(10) 0.2559(3) 0.35008(9) 0.0249(4) Uani d . 1 . . O
O4A 0.91505(10) 0.2169(3) 0.43864(8) 0.0238(4) Uani d . 1 . . O
N3A 1.01379(10) 0.4615(3) 0.29474(9) 0.0151(4) Uani d . 1 . . N
C9A 0.95699(13) 0.4070(3) 0.31157(11) 0.0160(4) Uani d . 1 . . C
H9A 0.913 0.4339 0.2883 0.019 Uiso calc R 1 . . H
C10A 0.96454(12) 0.3101(4) 0.36389(10) 0.0156(4) Uani d . 1 . . C
C11A 1.03071(13) 0.2695(3) 0.39806(11) 0.0178(5) Uani d . 1 . . C
H11A 1.0362 0.2055 0.4333 0.021 Uiso calc R 1 . . H
C12A 1.08841(12) 0.3252(4) 0.37911(11) 0.0183(5) Uani d . 1 . . C
H12A 1.1329 0.2975 0.4013 0.022 Uiso calc R 1 . . H
C13A 1.07874(12) 0.4223(4) 0.32696(11) 0.0164(4) Uani d . 1 . . C
H13A 1.117 0.4611 0.3139 0.02 Uiso calc R 1 . . H
C14A 1.00590(13) 0.5649(4) 0.23860(12) 0.0211(5) Uani d . 1 . . C
H14A 1.0509 0.5941 0.233 0.032 Uiso calc R 1 . . H
H14B 0.9807 0.6857 0.2388 0.032 Uiso calc R 1 . . H
H14C 0.981 0.4816 0.2078 0.032 Uiso calc R 1 . . H
C15A 0.89980(14) 0.2574(3) 0.38199(12) 0.0174(5) Uani d . 1 . . C
C16A 0.85552(17) 0.1744(5) 0.46150(14) 0.0318(6) Uani d . 1 . . C
H16A 0.871 0.1467 0.5021 0.048 Uiso calc R 1 . . H
H16B 0.8312 0.0617 0.4419 0.048 Uiso calc R 1 . . H
H16C 0.825 0.2866 0.4556 0.048 Uiso calc R 1 . . H
O3B 1.19225(10) 0.7516(3) 0.97842(9) 0.0232(4) Uani d . 1 . . O
O4B 1.12119(10) 0.6724(3) 0.89179(8) 0.0221(4) Uani d . 1 . . O
N3B 1.01698(11) 0.9216(3) 1.03202(9) 0.0167(4) Uani d . 1 . . N
C9B 1.07492(13) 0.8747(3) 1.01573(11) 0.0164(5) Uani d . 1 . . C
H9B 1.1183 0.9077 1.0391 0.02 Uiso calc R 1 . . H
C10B 1.06949(13) 0.7771(3) 0.96392(11) 0.0160(4) Uani d . 1 . . C
C11B 1.00428(14) 0.7304(4) 0.92891(11) 0.0190(5) Uani d . 1 . . C
H11B 1.0001 0.6679 0.8936 0.023 Uiso calc R 1 . . H
C12B 0.94554(14) 0.7783(4) 0.94745(12) 0.0216(5) Uani d . 1 . . C
H12B 0.9016 0.746 0.925 0.026 Uiso calc R 1 . . H
C13B 0.95306(13) 0.8737(4) 0.99928(12) 0.0191(5) Uani d . 1 . . C
H13B 0.914 0.9058 1.012 0.023 Uiso calc R 1 . . H
C14B 1.02209(14) 1.0252(4) 1.08756(12) 0.0246(5) Uani d . 1 . . C
H14D 0.9763 1.0477 1.0926 0.037 Uiso calc R 1 . . H
H14E 1.0452 1.1496 1.0873 0.037 Uiso calc R 1 . . H
H14F 1.048 0.9455 1.1188 0.037 Uiso calc R 1 . . H
C16B 1.18153(17) 0.6320(4) 0.86976(13) 0.0284(6) Uani d . 1 . . C
H16D 1.1666 0.5904 0.8302 0.043 Uiso calc R 1 . . H
H16E 1.2088 0.5293 0.8924 0.043 Uiso calc R 1 . . H
H16F 1.2091 0.7496 0.8722 0.043 Uiso calc R 1 . . H
C15B 1.13505(14) 0.7316(3) 0.94654(11) 0.0173(5) Uani d . 1 . . 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
Cl1A C5A . 1.720(2) ?
Cl2A C6A . 1.716(2) ?
O1A C1A . 1.242(3) ?
O2A C4A . 1.245(3) ?
N1A C7A . 1.155(4) ?
N2A C8A . 1.149(4) ?
C1A C2A . 1.444(3) ?
C1A C6A . 1.469(3) ?
C2A C3A . 1.390(3) ?
C2A C7A . 1.431(3) ?
C3A C8A . 1.438(3) ?
C3A C4A . 1.443(3) ?
C4A C5A . 1.472(3) ?
C5A C6A . 1.360(3) ?
Cl1B C5B . 1.722(2) ?
Cl2B C6B . 1.719(2) ?
O1B C1B . 1.245(3) ?
O2B C4B . 1.239(3) ?
N1B C7B . 1.154(4) ?
N2B C8B . 1.149(4) ?
C1B C2B . 1.453(3) ?
C1B C6B . 1.463(3) ?
C2B C3B . 1.382(3) ?
C2B C7B . 1.436(3) ?
C3B C8B . 1.438(3) ?
C3B C4B . 1.450(3) ?
C4B C5B . 1.470(3) ?
C5B C6B . 1.361(3) ?
O3A C15A . 1.195(3) ?
O4A C15A . 1.340(3) ?
O4A C16A . 1.453(3) ?
N3A C9A . 1.343(3) ?
N3A C13A . 1.354(3) ?
N3A C14A . 1.487(3) ?
C9A C10A . 1.387(3) ?
C9A H9A . 0.93 ?
C10A C11A . 1.392(3) ?
C10A C15A . 1.502(3) ?
C11A C12A . 1.388(4) ?
C11A H11A . 0.93 ?
C12A C13A . 1.380(4) ?
C12A H12A . 0.93 ?
C13A H13A . 0.93 ?
C14A H14A . 0.96 ?
C14A H14B . 0.96 ?
C14A H14C . 0.96 ?
C16A H16A . 0.96 ?
C16A H16B . 0.96 ?
C16A H16C . 0.96 ?
O3B C15B . 1.208(3) ?
O4B C15B . 1.330(3) ?
O4B C16B . 1.453(3) ?
N3B C9B . 1.344(3) ?
N3B C13B . 1.355(3) ?
N3B C14B . 1.483(3) ?
C9B C10B . 1.384(4) ?
C9B H9B . 0.93 ?
C10B C11B . 1.393(3) ?
C10B C15B . 1.498(4) ?
C11B C12B . 1.389(4) ?
C11B H11B . 0.93 ?
C12B C13B . 1.372(4) ?
C12B H12B . 0.93 ?
C13B H13B . 0.93 ?
C14B H14D . 0.96 ?
C14B H14E . 0.96 ?
C14B H14F . 0.96 ?
C16B H16D . 0.96 ?
C16B H16E . 0.96 ?
C16B H16F . 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 122.6(2) . . ?
O1A C1A C6A 122.4(2) . . ?
C2A C1A C6A 114.9(2) . . ?
C3A C2A C7A 120.5(2) . . ?
C3A C2A C1A 122.8(2) . . ?
C7A C2A C1A 116.7(2) . . ?
C2A C3A C8A 120.3(2) . . ?
C2A C3A C4A 122.4(2) . . ?
C8A C3A C4A 117.2(2) . . ?
O2A C4A C3A 122.8(2) . . ?
O2A C4A C5A 122.8(2) . . ?
C3A C4A C5A 114.4(2) . . ?
C6A C5A C4A 123.1(2) . . ?
C6A C5A Cl1A 121.65(18) . . ?
C4A C5A Cl1A 115.14(17) . . ?
C5A C6A C1A 122.0(2) . . ?
C5A C6A Cl2A 122.42(18) . . ?
C1A C6A Cl2A 115.52(17) . . ?
N1A C7A C2A 178.3(3) . . ?
N2A C8A C3A 177.0(3) . . ?
O1B C1B C2B 122.2(2) . . ?
O1B C1B C6B 122.8(2) . . ?
C2B C1B C6B 114.9(2) . . ?
C3B C2B C7B 121.9(2) . . ?
C3B C2B C1B 122.6(2) . . ?
C7B C2B C1B 115.3(2) . . ?
C2B C3B C8B 121.0(2) . . ?
C2B C3B C4B 122.4(2) . . ?
C8B C3B C4B 116.6(2) . . ?
O2B C4B C3B 122.9(2) . . ?
O2B C4B C5B 122.5(2) . . ?
C3B C4B C5B 114.6(2) . . ?
C6B C5B C4B 123.0(2) . . ?
C6B C5B Cl1B 121.37(18) . . ?
C4B C5B Cl1B 115.58(17) . . ?
C5B C6B C1B 122.2(2) . . ?
C5B C6B Cl2B 122.36(18) . . ?
C1B C6B Cl2B 115.41(17) . . ?
N1B C7B C2B 178.7(3) . . ?
N2B C8B C3B 179.6(3) . . ?
C15A O4A C16A 114.9(2) . . ?
C9A N3A C13A 122.1(2) . . ?
C9A N3A C14A 119.6(2) . . ?
C13A N3A C14A 118.3(2) . . ?
N3A C9A C10A 119.4(2) . . ?
N3A C9A H9A 120.3 . . ?
C10A C9A H9A 120.3 . . ?
C9A C10A C11A 119.7(2) . . ?
C9A C10A C15A 117.8(2) . . ?
C11A C10A C15A 122.5(2) . . ?
C12A C11A C10A 119.6(2) . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A H11A 120.2 . . ?
C13A C12A C11A 119.0(2) . . ?
C13A C12A H12A 120.5 . . ?
C11A C12A H12A 120.5 . . ?
N3A C13A C12A 120.2(2) . . ?
N3A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
N3A C14A H14A 109.5 . . ?
N3A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
N3A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
O3A C15A O4A 125.5(3) . . ?
O3A C15A C10A 124.1(2) . . ?
O4A C15A C10A 110.3(2) . . ?
O4A C16A H16A 109.5 . . ?
O4A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
O4A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15B O4B C16B 115.3(2) . . ?
C9B N3B C13B 121.7(2) . . ?
C9B N3B C14B 120.0(2) . . ?
C13B N3B C14B 118.3(2) . . ?
N3B C9B C10B 119.5(2) . . ?
N3B C9B H9B 120.3 . . ?
C10B C9B H9B 120.3 . . ?
C9B C10B C11B 119.9(2) . . ?
C9B C10B C15B 118.0(2) . . ?
C11B C10B C15B 122.1(2) . . ?
C12B C11B C10B 119.2(2) . . ?
C12B C11B H11B 120.4 . . ?
C10B C11B H11B 120.4 . . ?
C13B C12B C11B 119.3(2) . . ?
C13B C12B H12B 120.4 . . ?
C11B C12B H12B 120.4 . . ?
N3B C13B C12B 120.5(2) . . ?
N3B C13B H13B 119.7 . . ?
C12B C13B H13B 119.7 . . ?
N3B C14B H14D 109.5 . . ?
N3B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
N3B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
O4B C16B H16D 109.5 . . ?
O4B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
O4B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
O3B C15B O4B 125.8(3) . . ?
O3B C15B C10B 123.4(2) . . ?
O4B C15B C10B 110.8(2) . . ?

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 178.3(2) . . . . ?
C6A C1A C2A C3A -5.1(3) . . . . ?
O1A C1A C2A C7A -3.2(3) . . . . ?
C6A C1A C2A C7A 173.4(2) . . . . ?
C7A C2A C3A C8A -0.4(3) . . . . ?
C1A C2A C3A C8A 178.1(2) . . . . ?
C7A C2A C3A C4A -176.7(2) . . . . ?
C1A C2A C3A C4A 1.8(3) . . . . ?
C2A C3A C4A O2A -177.8(2) . . . . ?
C8A C3A C4A O2A 5.8(3) . . . . ?
C2A C3A C4A C5A 3.8(3) . . . . ?
C8A C3A C4A C5A -172.62(19) . . . . ?
O2A C4A C5A C6A 175.4(2) . . . . ?
C3A C4A C5A C6A -6.2(3) . . . . ?
O2A C4A C5A Cl1A -7.7(3) . . . . ?
C3A C4A C5A Cl1A 170.71(15) . . . . ?
C4A C5A C6A C1A 2.9(4) . . . . ?
Cl1A C5A C6A C1A -173.78(17) . . . . ?
C4A C5A C6A Cl2A -179.03(16) . . . . ?
Cl1A C5A C6A Cl2A 4.3(3) . . . . ?
O1A C1A C6A C5A 179.4(2) . . . . ?
C2A C1A C6A C5A 2.8(3) . . . . ?
O1A C1A C6A Cl2A 1.2(3) . . . . ?
C2A C1A C6A Cl2A -175.37(16) . . . . ?
C3A C2A C7A N1A 125(10) . . . . ?
C1A C2A C7A N1A -54(11) . . . . ?
C2A C3A C8A N2A 7(5) . . . . ?
C4A C3A C8A N2A -18E1(10) . . . . ?
O1B C1B C2B C3B -177.2(2) . . . . ?
C6B C1B C2B C3B 4.2(3) . . . . ?
O1B C1B C2B C7B 6.6(3) . . . . ?
C6B C1B C2B C7B -172.12(19) . . . . ?
C7B C2B C3B C8B -5.0(4) . . . . ?
C1B C2B C3B C8B 179.0(2) . . . . ?
C7B C2B C3B C4B 174.1(2) . . . . ?
C1B C2B C3B C4B -1.9(4) . . . . ?
C2B C3B C4B O2B -179.9(2) . . . . ?
C8B C3B C4B O2B -0.8(4) . . . . ?
C2B C3B C4B C5B -2.3(3) . . . . ?
C8B C3B C4B C5B 176.8(2) . . . . ?
O2B C4B C5B C6B -178.0(2) . . . . ?
C3B C4B C5B C6B 4.3(3) . . . . ?
O2B C4B C5B Cl1B 2.2(3) . . . . ?
C3B C4B C5B Cl1B -175.42(17) . . . . ?
C4B C5B C6B C1B -2.1(3) . . . . ?
Cl1B C5B C6B C1B 177.61(17) . . . . ?
C4B C5B C6B Cl2B 179.73(17) . . . . ?
Cl1B C5B C6B Cl2B -0.6(3) . . . . ?
O1B C1B C6B C5B 179.2(2) . . . . ?
C2B C1B C6B C5B -2.2(3) . . . . ?
O1B C1B C6B Cl2B -2.5(3) . . . . ?
C2B C1B C6B Cl2B 176.13(16) . . . . ?
C3B C2B C7B N1B -161(13) . . . . ?
C1B C2B C7B N1B 16(13) . . . . ?
C2B C3B C8B N2B 8E1(4) . . . . ?
C4B C3B C8B N2B -10E1(4) . . . . ?
C13A N3A C9A C10A 1.0(3) . . . . ?
C14A N3A C9A C10A 179.9(2) . . . . ?
N3A C9A C10A C11A -0.4(3) . . . . ?
N3A C9A C10A C15A 178.1(2) . . . . ?
C9A C10A C11A C12A -0.5(3) . . . . ?
C15A C10A C11A C12A -179.0(2) . . . . ?
C10A C11A C12A C13A 0.9(3) . . . . ?
C9A N3A C13A C12A -0.6(3) . . . . ?
C14A N3A C13A C12A -179.5(2) . . . . ?
C11A C12A C13A N3A -0.3(3) . . . . ?
C16A O4A C15A O3A -1.9(4) . . . . ?
C16A O4A C15A C10A 176.8(2) . . . . ?
C9A C10A C15A O3A 15.9(4) . . . . ?
C11A C10A C15A O3A -165.6(2) . . . . ?
C9A C10A C15A O4A -162.8(2) . . . . ?
C11A C10A C15A O4A 15.7(3) . . . . ?
C13B N3B C9B C10B 0.8(4) . . . . ?
C14B N3B C9B C10B 179.7(2) . . . . ?
N3B C9B C10B C11B 0.7(3) . . . . ?
N3B C9B C10B C15B 178.6(2) . . . . ?
C9B C10B C11B C12B -1.7(4) . . . . ?
C15B C10B C11B C12B -179.5(2) . . . . ?
C10B C11B C12B C13B 1.2(4) . . . . ?
C9B N3B C13B C12B -1.2(4) . . . . ?
C14B N3B C13B C12B 179.8(2) . . . . ?
C11B C12B C13B N3B 0.2(4) . . . . ?
C16B O4B C15B O3B -0.8(4) . . . . ?
C16B O4B C15B C10B 177.6(2) . . . . ?
C9B C10B C15B O3B 10.1(3) . . . . ?
C11B C10B C15B O3B -172.0(2) . . . . ?
C9B C10B C15B O4B -168.3(2) . . . . ?
C11B C10B C15B O4B 9.5(3) . . . . ?



# start Validation Reply Form


_vrf_PLAT129                     
;
PROBLEM: Unusual Space group Specified ..................    I1A1 Check 
RESPONSE: Alternative unit cell setting of Cc.
;
####################################################################### 
# 
# 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_p-amidoddq
_database_code_depnum_ccdc_archive 'CCDC 1584122'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-02-13 downloaded from the CCDC.
;

_audit_creation_date             2016-11-30T15:41:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H9 Cl3 N4 O3'
_chemical_formula_sum            'C15 H9 Cl2 N4 O3'
_chemical_formula_weight         364.16

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

# 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                   6.4226(3)
_cell_length_b                   11.3416(4)
_cell_length_c                   20.4418(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.438(4)
_cell_angle_gamma                90
_cell_volume                     1488.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8503
_cell_measurement_theta_min      4.317
_cell_measurement_theta_max      74.338
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             740
_exptl_absorpt_coefficient_mu    4.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.19237
_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_source                   'micro-focus sealed X-ray tube'
_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            19419
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_theta_min         4.33
_diffrn_reflns_theta_max         74.47
_diffrn_reflns_theta_full        74.47
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

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

# 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             2976
_reflns_number_gt                2590
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1636
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         2976
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1063P)²+0.8387P] 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         -0.549
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0022(5)
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 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_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 0.20915(10) 0.20149(5) 0.44072(3) 0.0338(2) Uani d . 1 . . Cl
Cl2 0.15034(11) 0.00314(6) 0.33136(3) 0.0363(2) Uani d . 1 . . Cl
O1 0.2022(3) -0.23500(17) 0.38377(9) 0.0366(5) Uani d . 1 . . O
O2 0.3308(3) 0.10271(16) 0.56856(9) 0.0342(4) Uani d . 1 . . O
N1 0.2795(4) -0.4068(2) 0.52390(13) 0.0437(6) Uani d . 1 . . N
N2 0.3507(4) -0.1556(2) 0.66355(12) 0.0422(6) Uani d . 1 . . N
C1 0.2293(4) -0.1577(2) 0.42597(13) 0.0330(6) Uani d . 1 . . C
C2 0.2738(4) -0.1855(2) 0.49422(13) 0.0317(6) Uani d . 1 . . C
C3 0.3038(4) -0.0989(2) 0.54170(13) 0.0318(6) Uani d . 1 . . C
C4 0.2960(4) 0.0255(2) 0.52616(14) 0.0322(6) Uani d . 1 . . C
C5 0.2400(4) 0.0535(2) 0.45816(14) 0.0328(6) Uani d . 1 . . C
C6 0.2099(4) -0.0316(2) 0.41112(13) 0.0318(6) Uani d . 1 . . C
C7 0.2777(5) -0.3082(2) 0.51082(13) 0.0348(6) Uani d . 1 . . C
C8 0.3321(4) -0.1302(2) 0.60960(14) 0.0344(6) Uani d . 1 . . C
O3 0.1809(3) 0.03464(17) 0.17929(10) 0.0379(5) Uani d . 1 . . O
N3 0.2559(4) 0.3976(2) 0.30410(11) 0.0347(5) Uani d . 1 . . N
N4 0.2743(4) 0.1547(2) 0.09593(11) 0.0360(5) Uani d . 1 . . N
H4A 0.2779 0.0977 0.0682 0.043 Uiso calc R 1 . . H
H4B 0.3031 0.2253 0.0838 0.043 Uiso calc R 1 . . H
C9 0.4133(5) 0.3888(2) 0.26187(14) 0.0374(6) Uani d . 1 . . C
H9 0.5295 0.4371 0.2669 0.045 Uiso calc R 1 . . H
C10 0.4027(5) 0.3085(2) 0.21126(14) 0.0369(6) Uani d . 1 . . C
H10 0.5098 0.3035 0.1816 0.044 Uiso calc R 1 . . H
C11 0.2297(5) 0.2348(2) 0.20507(13) 0.0335(6) Uani d . 1 . . C
C12 0.0683(5) 0.2476(2) 0.24853(13) 0.0336(6) Uani d . 1 . . C
H12 -0.0499 0.2005 0.2445 0.04 Uiso calc R 1 . . H
C13 0.0849(5) 0.3302(2) 0.29752(13) 0.0342(6) Uani d . 1 . . C
H13 -0.0234 0.3394 0.3264 0.041 Uiso calc R 1 . . H
C14 0.2780(5) 0.4809(3) 0.36016(15) 0.0432(7) Uani d . 1 . . C
H14A 0.4082 0.522 0.3577 0.065 Uiso calc PR 0.5 . . H
H14B 0.2743 0.4377 0.4005 0.065 Uiso calc PR 0.5 . . H
H14C 0.1656 0.5367 0.3585 0.065 Uiso calc PR 0.5 . . H
H14D 0.1572 0.4756 0.3867 0.065 Uiso calc PR 0.5 . . H
H14E 0.2911 0.5599 0.3439 0.065 Uiso calc PR 0.5 . . H
H14F 0.3998 0.4608 0.386 0.065 Uiso calc PR 0.5 . . H
C15 0.2245(4) 0.1336(2) 0.15756(13) 0.0336(6) Uani d . 1 . . 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
Cl1 C5 . 1.727(3) ?
Cl2 C6 . 1.711(3) ?
O1 C1 . 1.239(3) ?
O2 C4 . 1.249(3) ?
N1 C7 . 1.150(4) ?
N2 C8 . 1.143(4) ?
C1 C2 . 1.452(4) ?
C1 C6 . 1.466(4) ?
C2 C3 . 1.391(4) ?
C2 C7 . 1.433(4) ?
C3 C8 . 1.440(4) ?
C3 C4 . 1.446(4) ?
C4 C5 . 1.462(4) ?
C5 C6 . 1.373(4) ?
O3 C15 . 1.242(3) ?
N3 C13 . 1.343(4) ?
N3 C9 . 1.349(4) ?
N3 C14 . 1.489(4) ?
N4 C15 . 1.329(4) ?
N4 H4A . 0.86 ?
N4 H4B . 0.86 ?
C9 C10 . 1.379(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.394(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.389(4) ?
C11 C15 . 1.503(4) ?
C12 C13 . 1.374(4) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C14 H14D . 0.96 ?
C14 H14E . 0.96 ?
C14 H14F . 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 122.4(3) . . ?
O1 C1 C6 122.4(3) . . ?
C2 C1 C6 115.1(2) . . ?
C3 C2 C7 121.3(2) . . ?
C3 C2 C1 122.5(2) . . ?
C7 C2 C1 116.1(2) . . ?
C2 C3 C8 120.7(2) . . ?
C2 C3 C4 122.1(2) . . ?
C8 C3 C4 117.1(2) . . ?
O2 C4 C3 121.8(2) . . ?
O2 C4 C5 122.9(2) . . ?
C3 C4 C5 115.3(2) . . ?
C6 C5 C4 122.7(2) . . ?
C6 C5 Cl1 121.7(2) . . ?
C4 C5 Cl1 115.6(2) . . ?
C5 C6 C1 122.1(2) . . ?
C5 C6 Cl2 122.0(2) . . ?
C1 C6 Cl2 116.0(2) . . ?
N1 C7 C2 179.5(4) . . ?
N2 C8 C3 178.7(3) . . ?
C13 N3 C9 121.2(2) . . ?
C13 N3 C14 120.0(3) . . ?
C9 N3 C14 118.8(3) . . ?
C15 N4 H4A 120 . . ?
C15 N4 H4B 120 . . ?
H4A N4 H4B 120 . . ?
N3 C9 C10 120.4(3) . . ?
N3 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.2(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 C15 119.2(3) . . ?
C10 C11 C15 121.4(3) . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N3 C13 C12 120.7(3) . . ?
N3 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C14 H14D 109.5 . . ?
H14A C14 H14D 141.1 . . ?
H14B C14 H14D 56.3 . . ?
H14C C14 H14D 56.3 . . ?
N3 C14 H14E 109.5 . . ?
H14A C14 H14E 56.3 . . ?
H14B C14 H14E 141.1 . . ?
H14C C14 H14E 56.3 . . ?
H14D C14 H14E 109.5 . . ?
N3 C14 H14F 109.5 . . ?
H14A C14 H14F 56.3 . . ?
H14B C14 H14F 56.3 . . ?
H14C C14 H14F 141.1 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
O3 C15 N4 124.3(3) . . ?
O3 C15 C11 117.4(2) . . ?
N4 C15 C11 118.2(2) . . ?

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 -179.8(3) . . . . ?
C6 C1 C2 C3 -2.3(4) . . . . ?
O1 C1 C2 C7 -2.1(4) . . . . ?
C6 C1 C2 C7 175.4(3) . . . . ?
C7 C2 C3 C8 -2.3(4) . . . . ?
C1 C2 C3 C8 175.3(3) . . . . ?
C7 C2 C3 C4 -178.7(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 O2 -177.2(3) . . . . ?
C8 C3 C4 O2 6.3(4) . . . . ?
C2 C3 C4 C5 4.1(4) . . . . ?
C8 C3 C4 C5 -172.3(2) . . . . ?
O2 C4 C5 C6 177.4(3) . . . . ?
C3 C4 C5 C6 -4.0(4) . . . . ?
O2 C4 C5 Cl1 -3.8(4) . . . . ?
C3 C4 C5 Cl1 174.8(2) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
Cl1 C5 C6 C1 -178.0(2) . . . . ?
C4 C5 C6 Cl2 -178.5(2) . . . . ?
Cl1 C5 C6 Cl2 2.8(4) . . . . ?
O1 C1 C6 C5 180.0(3) . . . . ?
C2 C1 C6 C5 2.5(4) . . . . ?
O1 C1 C6 Cl2 -0.8(4) . . . . ?
C2 C1 C6 Cl2 -178.3(2) . . . . ?
C3 C2 C7 N1 13E1(4) . . . . ?
C1 C2 C7 N1 -5E1(4) . . . . ?
C2 C3 C8 N2 -74(14) . . . . ?
C4 C3 C8 N2 103(14) . . . . ?
C13 N3 C9 C10 -0.9(4) . . . . ?
C14 N3 C9 C10 176.8(3) . . . . ?
N3 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C12 2.6(4) . . . . ?
C9 C10 C11 C15 -170.4(3) . . . . ?
C10 C11 C12 C13 -1.6(4) . . . . ?
C15 C11 C12 C13 171.6(2) . . . . ?
C9 N3 C13 C12 1.9(4) . . . . ?
C14 N3 C13 C12 -175.8(2) . . . . ?
C11 C12 C13 N3 -0.6(4) . . . . ?
C12 C11 C15 O3 -46.0(4) . . . . ?
C10 C11 C15 O3 127.0(3) . . . . ?
C12 C11 C15 N4 136.5(3) . . . . ?
C10 C11 C15 N4 -50.5(4) . . . . ?


