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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_YSJ185
_database_code_depnum_ccdc_archive 'CCDC 1043927'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 N4'
_chemical_formula_weight         256.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   4.6304(17)
_cell_length_b                   14.479(6)
_cell_length_c                   8.886(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.402(7)
_cell_angle_gamma                90.00
_cell_volume                     595.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    286
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4405
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4414
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1078
_reflns_number_gt                661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1204P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1078
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2114
_refine_ls_wR_factor_gt          0.1842
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1513(5) 0.14914(16) 0.0611(3) 0.0403(8) Uani 1 1 d . . .
N2 N 0.3436(5) -0.03061(16) 0.1863(3) 0.0389(8) Uani 1 1 d . . .
C1 C 0.0566(6) 0.0680(2) 0.0215(3) 0.0358(8) Uani 1 1 d . . .
C2 C 0.1498(5) -0.0190(2) 0.0824(3) 0.0359(8) Uani 1 1 d . . .
C3 C 0.4533(6) 0.0548(2) 0.2359(3) 0.0367(8) Uani 1 1 d . . .
C4 C 0.6646(7) 0.0544(2) 0.3493(4) 0.0476(9) Uani 1 1 d . . .
H4A H 0.7303 -0.0015 0.3882 0.057 Uiso 1 1 calc R . .
C5 C 0.7748(7) 0.1354(3) 0.4034(4) 0.0569(11) Uani 1 1 d . . .
H5A H 0.9136 0.1343 0.4795 0.068 Uiso 1 1 calc R . .
C6 C 0.6808(8) 0.2198(3) 0.3453(4) 0.0578(11) Uani 1 1 d . . .
H6A H 0.7573 0.2745 0.3834 0.069 Uiso 1 1 calc R . .
C7 C 0.4790(7) 0.2230(2) 0.2340(4) 0.0485(9) Uani 1 1 d . . .
H7A H 0.4195 0.2799 0.1962 0.058 Uiso 1 1 calc R . .
C8 C 0.3587(6) 0.14133(19) 0.1749(3) 0.0391(8) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0397(15) 0.0337(15) 0.0477(17) 0.0000(11) -0.0016(12) -0.0022(11)
N2 0.0369(13) 0.0352(15) 0.0445(16) 0.0022(12) -0.0039(12) 0.0008(11)
C1 0.0320(16) 0.0354(16) 0.0398(17) 0.0003(14) 0.0001(14) 0.0009(13)
C2 0.0327(15) 0.0326(17) 0.0425(18) 0.0016(15) 0.0000(13) 0.0003(14)
C3 0.0312(15) 0.0423(18) 0.0367(18) -0.0009(13) 0.0007(14) -0.0008(12)
C4 0.0424(17) 0.054(2) 0.046(2) 0.0019(16) -0.0048(16) 0.0013(15)
C5 0.048(2) 0.072(3) 0.050(2) -0.0098(19) -0.0063(17) -0.0069(17)
C6 0.053(2) 0.055(2) 0.065(2) -0.016(2) -0.0006(19) -0.0134(18)
C7 0.0476(19) 0.0408(19) 0.057(2) -0.0053(16) -0.0005(18) -0.0059(15)
C8 0.0325(15) 0.0427(19) 0.0422(18) -0.0022(15) 0.0025(14) -0.0009(14)

_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
N1 C1 1.302(3) . ?
N1 C8 1.395(4) . ?
N2 C2 1.294(4) . ?
N2 C3 1.407(4) . ?
C1 C2 1.437(4) . ?
C1 C2 1.502(4) 3 ?
C2 C1 1.502(4) 3 ?
C3 C4 1.400(5) . ?
C3 C8 1.432(4) . ?
C4 C5 1.366(4) . ?
C5 C6 1.395(5) . ?
C6 C7 1.357(5) . ?
C7 C8 1.408(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 110.6(2) . . ?
C2 N2 C3 110.9(2) . . ?
N1 C1 C2 126.2(3) . . ?
N1 C1 C2 143.5(3) . 3 ?
C2 C1 C2 90.3(2) . 3 ?
N2 C2 C1 126.0(3) . . ?
N2 C2 C1 144.3(3) . 3 ?
C1 C2 C1 89.7(2) . 3 ?
C4 C3 N2 118.1(3) . . ?
C4 C3 C8 119.1(3) . . ?
N2 C3 C8 122.8(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 120.5(3) . . ?
C7 C6 C5 120.7(3) . . ?
C6 C7 C8 120.8(3) . . ?
N1 C8 C7 118.1(3) . . ?
N1 C8 C3 123.5(3) . . ?
C7 C8 C3 118.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.086
####################################################################### 
# 
# 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_chloro-CBDQ
_database_code_depnum_ccdc_archive 'CCDC 1043928'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-chloro-cyclobuta[1,2-b:3,4-b']diquinoxaline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H7 Cl N4'
_chemical_formula_weight         290.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8176(3)
_cell_length_b                   18.9603(13)
_cell_length_c                   8.7979(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.3270(10)
_cell_angle_gamma                90.00
_cell_volume                     634.07(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    31
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6175
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6882
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0174
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1152
_reflns_number_gt                855
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+0.1211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1152
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1115
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.0477(3) 0.66060(5) 1.18303(11) 0.0629(3) Uani 0.50 1 d P . .
N1 N 0.7855(4) 0.60811(8) 0.53344(17) 0.0514(4) Uani 1 1 d . . .
N2 N 0.5717(4) 0.50774(8) 0.76474(17) 0.0519(4) Uani 1 1 d . . .
C1 C 0.6265(4) 0.54859(10) 0.5057(2) 0.0482(5) Uani 1 1 d . . .
C2 C 0.5222(4) 0.49969(9) 0.6184(2) 0.0484(5) Uani 1 1 d . . .
C3 C 0.8454(4) 0.61989(10) 0.6901(2) 0.0486(5) Uani 1 1 d . . .
C4 C 0.7422(4) 0.57139(10) 0.8026(2) 0.0485(5) Uani 1 1 d . . .
C5 C 0.8115(5) 0.58737(11) 0.9572(2) 0.0557(5) Uani 1 1 d . . .
H5A H 0.7471 0.5558 1.0306 0.067 Uiso 1 1 calc R . .
C6 C 0.9736(5) 0.64910(12) 1.0009(2) 0.0603(6) Uani 1 1 d . . .
C7 C 1.0739(5) 0.69777(11) 0.8920(2) 0.0602(6) Uani 1 1 d . . .
H7A H 1.1821 0.7399 0.9233 0.072 Uiso 1 1 calc R . .
C8 C 1.0112(5) 0.68257(10) 0.7399(2) 0.0557(5) Uani 1 1 d . . .
H8A H 1.0801 0.7146 0.6683 0.067 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0796(7) 0.0526(6) 0.0557(6) -0.0109(4) 0.0026(5) 0.0008(5)
N1 0.0477(9) 0.0515(10) 0.0560(10) 0.0146(7) 0.0111(7) 0.0027(7)
N2 0.0495(9) 0.0515(10) 0.0566(11) 0.0139(7) 0.0143(7) 0.0052(7)
C1 0.0442(10) 0.0472(11) 0.0550(11) 0.0146(8) 0.0141(8) 0.0049(8)
C2 0.0451(10) 0.0478(11) 0.0542(12) 0.0155(8) 0.0147(8) 0.0068(8)
C3 0.0395(9) 0.0513(11) 0.0559(11) 0.0134(9) 0.0094(7) 0.0068(8)
C4 0.0402(9) 0.0502(11) 0.0564(11) 0.0143(9) 0.0118(7) 0.0091(8)
C5 0.0496(11) 0.0614(13) 0.0574(12) 0.0162(10) 0.0123(8) 0.0089(9)
C6 0.0487(11) 0.0699(14) 0.0628(13) 0.0116(10) 0.0071(9) 0.0120(10)
C7 0.0518(11) 0.0598(13) 0.0679(14) 0.0091(10) 0.0008(9) 0.0022(9)
C8 0.0492(11) 0.0554(12) 0.0625(12) 0.0166(10) 0.0059(8) 0.0013(9)

_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 C6 1.616(2) . ?
N1 C1 1.294(2) . ?
N1 C3 1.394(2) . ?
N2 C2 1.293(2) . ?
N2 C4 1.397(2) . ?
C1 C2 1.440(2) . ?
C1 C2 1.496(3) 3_666 ?
C2 C1 1.496(3) 3_666 ?
C3 C8 1.398(3) . ?
C3 C4 1.433(2) . ?
C4 C5 1.394(3) . ?
C5 C6 1.362(3) . ?
C6 C7 1.408(3) . ?
C7 C8 1.368(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 110.93(15) . . ?
C2 N2 C4 111.19(15) . . ?
N1 C1 C2 125.90(18) . . ?
N1 C1 C2 144.21(16) . 3_666 ?
C2 C1 C2 89.89(15) . 3_666 ?
N2 C2 C1 125.84(18) . . ?
N2 C2 C1 144.05(16) . 3_666 ?
C1 C2 C1 90.11(15) . 3_666 ?
N1 C3 C8 118.31(16) . . ?
N1 C3 C4 123.36(17) . . ?
C8 C3 C4 118.33(17) . . ?
C5 C4 N2 117.56(16) . . ?
C5 C4 C3 119.66(18) . . ?
N2 C4 C3 122.78(17) . . ?
C6 C5 C4 120.11(17) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 Cl1 115.37(16) . . ?
C7 C6 Cl1 123.52(19) . . ?
C8 C7 C6 119.5(2) . . ?
C7 C8 C3 121.26(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_dichloro-CBDQ
_database_code_depnum_ccdc_archive 'CCDC 1043929'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,8-dichloro-cyclobuta[1,2-b:3,4-b']diquinoxaline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 Cl2 N4'
_chemical_formula_weight         325.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8194(2)
_cell_length_b                   19.4986(8)
_cell_length_c                   8.9236(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.974(2)
_cell_angle_gamma                90.00
_cell_volume                     654.52(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    55
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6447
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8768
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1193
_reflns_number_gt                881
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.9229P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1193
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.0310(3) 0.66152(5) 0.29099(11) 0.0537(4) Uani 1 1 d . . .
C1 C 0.4811(9) 0.49914(16) 0.8828(4) 0.0343(8) Uani 1 1 d . . .
C2 C 0.3729(9) 0.54742(16) 0.9878(4) 0.0339(8) Uani 1 1 d . . .
C3 C 0.1602(9) 0.61626(16) 0.7953(4) 0.0343(8) Uani 1 1 d . . .
C4 C -0.0047(9) 0.67728(17) 0.7378(4) 0.0396(8) Uani 1 1 d . . .
H4A H -0.0772 0.7087 0.8047 0.048 Uiso 1 1 calc R . .
C5 C -0.0616(10) 0.69174(17) 0.5854(4) 0.0415(9) Uani 1 1 d . . .
H5A H -0.1684 0.7328 0.5494 0.050 Uiso 1 1 calc R . .
C6 C 0.0432(9) 0.64383(17) 0.4842(4) 0.0371(8) Uani 1 1 d . . .
C7 C 0.2035(9) 0.58347(16) 0.5346(4) 0.0357(8) Uani 1 1 d . . .
H7A H 0.2696 0.5524 0.4654 0.043 Uiso 1 1 calc R . .
C8 C 0.2683(8) 0.56836(16) 0.6903(4) 0.0331(8) Uani 1 1 d . . .
N1 N 0.4388(7) 0.50640(14) 0.7362(3) 0.0362(7) Uani 1 1 d . . .
N2 N 0.2140(7) 0.60565(14) 0.9524(3) 0.0378(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0644(7) 0.0463(6) 0.0483(6) 0.0101(4) 0.0037(5) 0.0018(5)
C1 0.0349(19) 0.0306(17) 0.0373(18) -0.0023(14) 0.0058(14) 0.0017(14)
C2 0.0327(18) 0.0328(17) 0.0356(18) -0.0037(14) 0.0042(15) -0.0003(15)
C3 0.0326(18) 0.0290(17) 0.0401(19) -0.0025(14) 0.0031(15) 0.0007(14)
C4 0.039(2) 0.0316(17) 0.047(2) -0.0070(15) 0.0052(16) 0.0029(15)
C5 0.042(2) 0.0291(18) 0.050(2) 0.0020(16) -0.0012(17) 0.0026(15)
C6 0.0326(19) 0.0345(17) 0.043(2) 0.0014(15) 0.0024(15) -0.0059(15)
C7 0.0362(19) 0.0320(18) 0.0392(18) -0.0034(14) 0.0070(15) -0.0024(15)
C8 0.0299(17) 0.0284(16) 0.0405(18) -0.0031(14) 0.0042(14) -0.0029(14)
N1 0.0388(16) 0.0300(14) 0.0401(16) -0.0022(12) 0.0079(12) 0.0034(12)
N2 0.0403(17) 0.0335(15) 0.0393(16) -0.0041(12) 0.0057(13) 0.0047(13)

_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 C6 1.733(4) . ?
C1 N1 1.297(4) . ?
C1 C2 1.438(4) . ?
C1 C2 1.498(5) 3_667 ?
C2 N2 1.300(4) . ?
C2 C1 1.499(5) 3_667 ?
C3 N2 1.397(4) . ?
C3 C4 1.401(5) . ?
C3 C8 1.434(5) . ?
C4 C5 1.368(5) . ?
C5 C6 1.405(5) . ?
C6 C7 1.366(5) . ?
C7 C8 1.400(5) . ?
C8 N1 1.400(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 125.8(3) . . ?
N1 C1 C2 143.9(3) . 3_667 ?
C2 C1 C2 90.3(3) . 3_667 ?
N2 C2 C1 126.0(3) . . ?
N2 C2 C1 144.3(3) . 3_667 ?
C1 C2 C1 89.7(3) . 3_667 ?
N2 C3 C4 118.2(3) . . ?
N2 C3 C8 123.4(3) . . ?
C4 C3 C8 118.4(3) . . ?
C5 C4 C3 121.5(3) . . ?
C4 C5 C6 119.2(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 Cl1 119.0(3) . . ?
C5 C6 Cl1 119.4(3) . . ?
C6 C7 C8 120.0(3) . . ?
N1 C8 C7 117.8(3) . . ?
N1 C8 C3 122.9(3) . . ?
C7 C8 C3 119.4(3) . . ?
C1 N1 C8 111.1(3) . . ?
C2 N2 C3 110.7(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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_dichloro-CBDQ-cocrystal
_database_code_depnum_ccdc_archive 'CCDC 1043930'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,8-dichloro-cyclobuta[1,2-b:3,4-b'] diquinoxaline and 2,9-dichloro-cyclobuta[1,2-b:3,4-b'] diquinoxaline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H4 Cl2 N4'
_chemical_formula_weight         323.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7573(16)
_cell_length_b                   7.941(3)
_cell_length_c                   8.892(3)
_cell_angle_alpha                92.898(10)
_cell_angle_beta                 100.560(11)
_cell_angle_gamma                94.347(10)
_cell_volume                     328.57(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    70
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             162
_exptl_absorpt_coefficient_mu    0.493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4867
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5502
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1170
_reflns_number_gt                951
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+6.4320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1170
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1459
_refine_ls_R_factor_gt           0.1272
_refine_ls_wR_factor_ref         0.3685
_refine_ls_wR_factor_gt          0.3611
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_restrained_S_all      1.273
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.9334(18) -0.4893(11) 0.7468(9) 0.030(2) Uani 1 1 d . . .
N2 N -0.6242(19) -0.2891(11) 1.0259(9) 0.032(2) Uani 1 1 d . . .
Cl1 Cl -0.0240(8) 0.0519(5) 0.7142(5) 0.0415(13) Uani 0.749(9) 1 d P A 1
Cl1' Cl -0.320(3) -0.1948(18) 0.4236(15) 0.055(5) Uani 0.251(9) 1 d P A 2
C1 C -0.715(2) -0.3635(13) 0.7459(11) 0.029(2) Uani 1 1 d . . .
C2 C -0.640(2) -0.3306(15) 0.6042(12) 0.037(3) Uani 1 1 d . A .
H2B H -0.7370 -0.3923 0.5158 0.045 Uiso 1 1 calc R . .
C3 C -0.423(2) -0.2069(14) 0.5942(13) 0.036(3) Uani 1 1 d . . .
C4 C -0.283(2) -0.1122(14) 0.7275(13) 0.036(3) Uani 1 1 d . A .
C5 C -0.350(2) -0.1434(14) 0.8673(13) 0.036(3) Uani 1 1 d . . .
H5A H -0.2495 -0.0810 0.9546 0.043 Uiso 1 1 calc R A .
C6 C -0.566(2) -0.2673(13) 0.8809(11) 0.028(2) Uani 1 1 d . A .
C7 C -0.831(2) -0.4034(12) 1.0208(11) 0.027(2) Uani 1 1 d . . .
C8 C -0.985(2) -0.5012(12) 0.8847(11) 0.026(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.032(5) 0.034(5) 0.023(5) 0.000(4) 0.002(4) -0.002(4)
N2 0.034(5) 0.041(5) 0.019(4) -0.002(4) 0.003(4) -0.003(4)
Cl1 0.042(2) 0.044(2) 0.040(2) 0.0049(16) 0.0133(16) -0.0078(16)
Cl1' 0.060(9) 0.065(9) 0.045(8) 0.009(6) 0.016(6) 0.012(7)
C1 0.032(5) 0.032(6) 0.021(5) -0.003(4) 0.004(4) 0.002(4)
C2 0.038(6) 0.049(7) 0.024(6) -0.002(5) 0.005(5) 0.003(5)
C3 0.040(6) 0.039(6) 0.032(6) 0.005(5) 0.008(5) 0.009(5)
C4 0.034(6) 0.033(6) 0.044(7) 0.006(5) 0.010(5) 0.003(5)
C5 0.036(6) 0.031(6) 0.037(6) 0.002(5) 0.002(5) -0.005(5)
C6 0.029(5) 0.030(5) 0.024(5) 0.002(4) 0.005(4) 0.005(4)
C7 0.034(5) 0.025(5) 0.020(5) -0.006(4) 0.005(4) 0.000(4)
C8 0.028(5) 0.025(5) 0.025(5) -0.003(4) 0.002(4) 0.002(4)

_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
N1 C8 1.301(13) . ?
N1 C1 1.388(13) . ?
N2 C7 1.280(13) . ?
N2 C6 1.384(12) . ?
Cl1 C4 1.749(11) . ?
Cl1' C3 1.681(16) . ?
C1 C2 1.402(14) . ?
C1 C6 1.428(14) . ?
C2 C3 1.389(16) . ?
C3 C4 1.398(16) . ?
C4 C5 1.368(16) . ?
C5 C6 1.394(14) . ?
C7 C8 1.448(13) . ?
C7 C8 1.509(13) 2_347 ?
C8 C7 1.509(13) 2_347 ?

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
C8 N1 C1 110.4(8) . . ?
C7 N2 C6 110.8(8) . . ?
N1 C1 C2 117.4(9) . . ?
N1 C1 C6 123.3(9) . . ?
C2 C1 C6 119.2(10) . . ?
C3 C2 C1 120.8(10) . . ?
C2 C3 C4 119.0(10) . . ?
C2 C3 Cl1' 117.0(10) . . ?
C4 C3 Cl1' 123.7(10) . . ?
C5 C4 C3 121.3(10) . . ?
C5 C4 Cl1 119.5(9) . . ?
C3 C4 Cl1 119.3(9) . . ?
C4 C5 C6 121.0(10) . . ?
N2 C6 C5 117.5(9) . . ?
N2 C6 C1 123.8(9) . . ?
C5 C6 C1 118.7(9) . . ?
N2 C7 C8 126.0(9) . . ?
N2 C7 C8 144.6(9) . 2_347 ?
C8 C7 C8 89.4(8) . 2_347 ?
N1 C8 C7 125.7(9) . . ?
N1 C8 C7 143.7(9) . 2_347 ?
C7 C8 C7 90.6(8) . 2_347 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.135
####################################################################### 
# 
# 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_tetrachloro-CBDQ
_database_code_depnum_ccdc_archive 'CCDC 1043931'
_audit_update_record             
;
2015-01-16 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2,3,8,9-tetrachloro-cyclobuta[1,2-b:3,4-b']diquinoxaline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H4 Cl4 N4'
_chemical_formula_weight         394.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8383(2)
_cell_length_b                   6.0989(2)
_cell_length_c                   10.5832(4)
_cell_angle_alpha                82.636(2)
_cell_angle_beta                 76.077(2)
_cell_angle_gamma                82.498(2)
_cell_volume                     360.80(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    40
_cell_measurement_theta_min      15
_cell_measurement_theta_max      15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4255
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1276
_reflns_number_gt                1089
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.0489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1276
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0793
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.27493(9) 0.27392(9) -0.03343(5) 0.0457(2) Uani 1 1 d . . .
Cl2 Cl 0.78733(9) 0.35818(8) -0.19998(5) 0.0443(2) Uani 1 1 d . . .
C1 C 0.3863(3) -0.4313(3) -0.41961(17) 0.0284(4) Uani 1 1 d . . .
C2 C 0.3971(3) -0.1688(3) -0.29557(17) 0.0288(4) Uani 1 1 d . . .
C3 C 0.2926(3) -0.0427(3) -0.19178(18) 0.0321(4) Uani 1 1 d . . .
H3A H 0.1422 -0.0683 -0.1419 0.038 Uiso 1 1 calc R . .
C4 C 0.4084(3) 0.1185(3) -0.16228(17) 0.0318(4) Uani 1 1 d . . .
C5 C 0.6369(3) 0.1570(3) -0.23573(18) 0.0300(4) Uani 1 1 d . . .
C6 C 0.7442(3) 0.0350(3) -0.33844(19) 0.0314(4) Uani 1 1 d . . .
H6A H 0.8952 0.0618 -0.3867 0.038 Uiso 1 1 calc R . .
C7 C 0.6288(3) -0.1290(3) -0.37124(17) 0.0280(4) Uani 1 1 d . . .
C8 C 0.6200(3) -0.3913(3) -0.49565(17) 0.0277(4) Uani 1 1 d . . .
N1 N 0.2674(3) -0.3281(2) -0.32116(15) 0.0309(4) Uani 1 1 d . . .
N2 N 0.7480(3) -0.2451(3) -0.47727(15) 0.0311(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0491(4) 0.0495(4) 0.0400(3) -0.0240(2) -0.0037(2) -0.0039(3)
Cl2 0.0447(3) 0.0391(3) 0.0569(4) -0.0214(2) -0.0151(3) -0.0096(2)
C1 0.0292(10) 0.0258(10) 0.0310(9) -0.0061(8) -0.0047(8) -0.0064(8)
C2 0.0290(10) 0.0283(10) 0.0302(9) -0.0042(8) -0.0064(8) -0.0066(8)
C3 0.0297(10) 0.0342(11) 0.0302(10) -0.0071(8) -0.0002(8) -0.0045(8)
C4 0.0362(11) 0.0303(10) 0.0304(10) -0.0082(8) -0.0093(8) -0.0003(8)
C5 0.0333(11) 0.0258(10) 0.0345(10) -0.0071(8) -0.0126(8) -0.0030(8)
C6 0.0287(10) 0.0292(10) 0.0375(10) -0.0066(8) -0.0064(8) -0.0062(8)
C7 0.0287(10) 0.0253(9) 0.0303(9) -0.0063(7) -0.0050(8) -0.0040(8)
C8 0.0267(10) 0.0270(10) 0.0292(9) -0.0060(7) -0.0027(7) -0.0064(8)
N1 0.0304(9) 0.0294(8) 0.0326(8) -0.0074(7) -0.0023(7) -0.0076(7)
N2 0.0296(9) 0.0302(9) 0.0335(8) -0.0097(7) -0.0014(7) -0.0079(7)

_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 C4 1.7300(18) . ?
Cl2 C5 1.7264(18) . ?
C1 N1 1.292(2) . ?
C1 C8 1.441(2) . ?
C1 C8 1.500(2) 2_644 ?
C2 C3 1.394(3) . ?
C2 N1 1.396(2) . ?
C2 C7 1.430(3) . ?
C3 C4 1.370(3) . ?
C4 C5 1.405(3) . ?
C5 C6 1.373(3) . ?
C6 C7 1.397(3) . ?
C7 N2 1.394(2) . ?
C8 N2 1.296(2) . ?
C8 C1 1.500(2) 2_644 ?

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
N1 C1 C8 126.15(17) . . ?
N1 C1 C8 144.13(18) . 2_644 ?
C8 C1 C8 89.72(14) . 2_644 ?
C3 C2 N1 117.74(16) . . ?
C3 C2 C7 119.17(16) . . ?
N1 C2 C7 123.09(15) . . ?
C4 C3 C2 120.83(17) . . ?
C3 C4 C5 120.19(17) . . ?
C3 C4 Cl1 120.07(15) . . ?
C5 C4 Cl1 119.74(14) . . ?
C6 C5 C4 120.20(17) . . ?
C6 C5 Cl2 118.71(15) . . ?
C4 C5 Cl2 121.09(14) . . ?
C5 C6 C7 120.70(18) . . ?
N2 C7 C6 117.50(16) . . ?
N2 C7 C2 123.60(15) . . ?
C6 C7 C2 118.90(16) . . ?
N2 C8 C1 125.93(16) . . ?
N2 C8 C1 143.79(17) . 2_644 ?
C1 C8 C1 90.28(14) . 2_644 ?
C1 N1 C2 110.73(15) . . ?
C8 N2 C7 110.50(15) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.050
