# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1041847'
_audit_update_record             
;
2015-01-03 deposited with the CCDC.
2015-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
3-Chloroisonicotinic acid 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl N O2'
_chemical_formula_sum            'C6 H4 Cl N O2'
_chemical_formula_weight         157.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.1603(2)
_cell_length_b                   7.2376(2)
_cell_length_c                   7.4950(3)
_cell_angle_alpha                63.2313(14)
_cell_angle_beta                 69.7053(14)
_cell_angle_gamma                64.9840(15)
_cell_volume                     308.331(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1391
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7372
_exptl_absorpt_correction_T_max  0.9580
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2782
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.43
_reflns_number_total             1406
_reflns_number_gt                1263
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL/PC (Sheldrick, 1995)'
_computing_publication_material  
;
SHELXL97 and local procedures
;

_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)+(0.0371P)²+0.1858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1406
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.32204(6) 0.08476(6) 0.76652(5) 0.02102(15) Uani 1 1 d . . .
O1 O 0.22648(17) 0.31940(17) 1.04009(16) 0.0170(2) Uani 1 1 d . . .
O2 O 0.26293(18) 0.65172(18) 0.90414(16) 0.0181(3) Uani 1 1 d . . .
H2 H 0.2591 0.6293 1.0253 0.027 Uiso 1 1 calc R . .
N1 N 0.23714(19) 0.6112(2) 0.27746(18) 0.0142(3) Uani 1 1 d . . .
C2 C 0.2696(2) 0.4087(2) 0.4130(2) 0.0144(3) Uani 1 1 d . . .
H2A H 0.2915 0.2948 0.3700 0.017 Uiso 1 1 calc R . .
C7 C 0.2431(2) 0.4836(2) 0.8960(2) 0.0130(3) Uani 1 1 d . . .
C6 C 0.2063(2) 0.7733(2) 0.3370(2) 0.0149(3) Uani 1 1 d . . .
H6 H 0.1826 0.9183 0.2410 0.018 Uiso 1 1 calc R . .
C3 C 0.2727(2) 0.3563(2) 0.6155(2) 0.0132(3) Uani 1 1 d . . .
C5 C 0.2083(2) 0.7335(2) 0.5355(2) 0.0142(3) Uani 1 1 d . . .
H5 H 0.1870 0.8509 0.5733 0.017 Uiso 1 1 calc R . .
C4 C 0.2413(2) 0.5222(2) 0.6804(2) 0.0122(3) 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 0.0355(3) 0.0125(2) 0.0144(2) -0.00304(15) -0.00486(16) -0.00887(16)
O1 0.0247(6) 0.0149(5) 0.0113(5) -0.0032(4) -0.0043(4) -0.0072(5)
O2 0.0317(6) 0.0194(6) 0.0088(5) -0.0045(4) -0.0038(4) -0.0140(5)
N1 0.0156(6) 0.0166(6) 0.0119(6) -0.0054(5) -0.0032(5) -0.0057(5)
C2 0.0144(7) 0.0181(7) 0.0138(7) -0.0078(6) -0.0014(5) -0.0066(6)
C7 0.0121(6) 0.0156(7) 0.0112(7) -0.0058(6) -0.0019(5) -0.0038(5)
C6 0.0176(7) 0.0149(7) 0.0119(7) -0.0038(6) -0.0043(5) -0.0050(6)
C3 0.0145(7) 0.0119(7) 0.0120(7) -0.0025(5) -0.0027(5) -0.0051(5)
C5 0.0159(7) 0.0163(7) 0.0124(7) -0.0065(6) -0.0027(5) -0.0055(6)
C4 0.0115(6) 0.0156(7) 0.0104(6) -0.0046(5) -0.0019(5) -0.0052(5)

_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 C3 1.7189(15) . ?
O1 C7 1.2112(18) . ?
O2 C7 1.3125(18) . ?
O2 H2 0.8400 . ?
N1 C2 1.3298(19) . ?
N1 C6 1.3449(19) . ?
C2 C3 1.395(2) . ?
C2 H2A 0.9500 . ?
C7 C4 1.5149(19) . ?
C6 C5 1.386(2) . ?
C6 H6 0.9500 . ?
C3 C4 1.397(2) . ?
C5 C4 1.397(2) . ?
C5 H5 0.9500 . ?

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
C7 O2 H2 109.5 . . ?
C2 N1 C6 118.93(12) . . ?
N1 C2 C3 122.85(13) . . ?
N1 C2 H2A 118.6 . . ?
C3 C2 H2A 118.6 . . ?
O1 C7 O2 125.37(13) . . ?
O1 C7 C4 123.77(13) . . ?
O2 C7 C4 110.85(12) . . ?
N1 C6 C5 121.48(14) . . ?
N1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C2 C3 C4 119.13(13) . . ?
C2 C3 Cl1 116.08(11) . . ?
C4 C3 Cl1 124.77(11) . . ?
C6 C5 C4 120.54(14) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C4 C3 117.08(13) . . ?
C5 C4 C7 119.35(13) . . ?
C3 C4 C7 123.57(13) . . ?

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
C6 N1 C2 C3 0.1(2) . . . . ?
C2 N1 C6 C5 0.2(2) . . . . ?
N1 C2 C3 C4 -0.2(2) . . . . ?
N1 C2 C3 Cl1 -178.79(11) . . . . ?
N1 C6 C5 C4 -0.4(2) . . . . ?
C6 C5 C4 C3 0.3(2) . . . . ?
C6 C5 C4 C7 179.87(13) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
Cl1 C3 C4 C5 178.43(11) . . . . ?
C2 C3 C4 C7 -179.54(13) . . . . ?
Cl1 C3 C4 C7 -1.1(2) . . . . ?
O1 C7 C4 C5 163.96(14) . . . . ?
O2 C7 C4 C5 -15.43(18) . . . . ?
O1 C7 C4 C3 -16.5(2) . . . . ?
O2 C7 C4 C3 164.08(13) . . . . ?

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
O2 H2 N1 0.84 1.79 2.6264(15) 174.1 1_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.061
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1041848'
_audit_update_record             
;
2015-01-03 deposited with the CCDC.
2015-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
3-Chloroisonicotinic acid 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl N O2'
_chemical_formula_sum            'C6 H4 Cl N O2'
_chemical_formula_weight         157.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.3267(2)
_cell_length_b                   6.6413(2)
_cell_length_c                   12.6512(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2254(15)
_cell_angle_gamma                90.00
_cell_volume                     615.13(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    1522
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7027
_exptl_absorpt_correction_T_max  0.9231
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(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  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2596
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1410
_reflns_number_gt                1284
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL/PC (Sheldrick, 1995)'
_computing_publication_material  
;
SHELXL97 and local procedures
;

_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)+(0.0416P)²+0.3078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1410
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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 0.82621(4) 0.34399(5) 0.94515(2) 0.01493(13) Uani 1 1 d . . .
O2 O 0.60059(13) 0.34192(14) 0.62026(7) 0.0137(2) Uani 1 1 d . . .
H2 H 0.6723 0.3404 0.5700 0.021 Uiso 1 1 calc R . .
O1 O 0.84612(13) 0.22877(16) 0.71514(7) 0.0167(2) Uani 1 1 d . . .
N1 N 0.30977(15) 0.18841(17) 0.95583(8) 0.0135(2) Uani 1 1 d . . .
C5 C 0.37546(18) 0.1955(2) 0.77275(10) 0.0139(3) Uani 1 1 d . . .
H5 H 0.3334 0.1795 0.7013 0.017 Uiso 1 1 calc R . .
C6 C 0.25654(18) 0.16495(19) 0.85371(10) 0.0143(3) Uani 1 1 d . . .
H6 H 0.1341 0.1264 0.8366 0.017 Uiso 1 1 calc R . .
C2 C 0.48221(18) 0.24268(19) 0.97893(10) 0.0132(3) Uani 1 1 d . . .
H2A H 0.5195 0.2611 1.0510 0.016 Uiso 1 1 calc R . .
C4 C 0.55667(17) 0.24973(18) 0.79562(10) 0.0116(3) Uani 1 1 d . . .
C7 C 0.68555(17) 0.27421(19) 0.70641(10) 0.0121(3) Uani 1 1 d . . .
C3 C 0.60942(17) 0.27331(19) 0.90191(9) 0.0116(3) 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 0.01228(18) 0.0203(2) 0.01207(18) -0.00232(11) -0.00150(11) -0.00047(11)
O2 0.0141(4) 0.0196(5) 0.0076(4) 0.0004(3) 0.0030(3) 0.0017(4)
O1 0.0129(5) 0.0255(5) 0.0119(4) 0.0006(4) 0.0019(3) 0.0014(4)
N1 0.0157(5) 0.0137(5) 0.0112(5) -0.0004(4) 0.0025(4) 0.0006(4)
C5 0.0158(6) 0.0162(6) 0.0096(6) -0.0014(5) 0.0007(5) -0.0002(5)
C6 0.0129(6) 0.0164(6) 0.0135(6) -0.0011(5) 0.0010(5) -0.0009(5)
C2 0.0165(6) 0.0141(6) 0.0091(6) -0.0004(5) 0.0013(5) 0.0016(5)
C4 0.0128(6) 0.0116(6) 0.0106(6) 0.0003(4) 0.0022(4) 0.0010(4)
C7 0.0150(6) 0.0123(6) 0.0091(5) -0.0016(4) 0.0019(4) -0.0013(5)
C3 0.0117(6) 0.0111(6) 0.0118(6) -0.0001(5) -0.0002(4) 0.0008(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
Cl1 C3 1.7248(13) . ?
O2 C7 1.3134(15) . ?
O2 H2 0.8400 . ?
O1 C7 1.2154(16) . ?
N1 C2 1.3353(17) . ?
N1 C6 1.3439(16) . ?
C5 C6 1.3852(18) . ?
C5 C4 1.3950(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C2 C3 1.3892(17) . ?
C2 H2A 0.9500 . ?
C4 C3 1.3936(17) . ?
C4 C7 1.5082(16) . ?

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
C7 O2 H2 109.5 . . ?
C2 N1 C6 118.59(11) . . ?
C6 C5 C4 120.36(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C5 121.76(12) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N1 C2 C3 122.75(11) . . ?
N1 C2 H2A 118.6 . . ?
C3 C2 H2A 118.6 . . ?
C3 C4 C5 117.08(11) . . ?
C3 C4 C7 123.48(11) . . ?
C5 C4 C7 119.42(11) . . ?
O1 C7 O2 125.90(11) . . ?
O1 C7 C4 122.50(11) . . ?
O2 C7 C4 111.56(11) . . ?
C2 C3 C4 119.46(11) . . ?
C2 C3 Cl1 116.88(9) . . ?
C4 C3 Cl1 123.65(10) . . ?

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
C2 N1 C6 C5 0.00(19) . . . . ?
C4 C5 C6 N1 0.8(2) . . . . ?
C6 N1 C2 C3 -0.87(19) . . . . ?
C6 C5 C4 C3 -0.78(19) . . . . ?
C6 C5 C4 C7 177.60(12) . . . . ?
C3 C4 C7 O1 33.39(19) . . . . ?
C5 C4 C7 O1 -144.88(14) . . . . ?
C3 C4 C7 O2 -148.93(12) . . . . ?
C5 C4 C7 O2 32.81(16) . . . . ?
N1 C2 C3 C4 0.9(2) . . . . ?
N1 C2 C3 Cl1 179.76(10) . . . . ?
C5 C4 C3 C2 -0.04(18) . . . . ?
C7 C4 C3 C2 -178.34(12) . . . . ?
C5 C4 C3 Cl1 -178.82(10) . . . . ?
C7 C4 C3 Cl1 2.87(18) . . . . ?

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
O2 H2 N1 0.84 1.80 2.6390(14) 172.9 4_665

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_III
_database_code_depnum_ccdc_archive 'CCDC 1041849'
# CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2014). 
# CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix 
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-02-06 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2014/7 and CIFFIX'

_shelx_SHELXL_version_number     2014/7

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl N O2'
_chemical_formula_sum            'C6 H4 Cl N O2'
_chemical_formula_weight         157.55

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   3.6779(1)
_cell_length_b                   6.9371(1)
_cell_length_c                   7.0372(2)
_cell_angle_alpha                61.6975(14)
_cell_angle_beta                 80.0002(12)
_cell_angle_gamma                89.5122(12)
_cell_volume                     155.117(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    667
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_F_000             80
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.538
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8137
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 2006)'
_exptl_absorpt_special_details   
; 
In addition to absorption, multi-scan techniques also correct other slowly 
varying changes in scale factor over reciprocal space, such as those caused 
by x-ray beam inhomogeneity, goniometer imperfection, crystal longer than 
the x-ray beam cross section, absorption by the crystal mounting fibre etc. 
These account, by and large, for much of the difference between estimated 
values of Tmin and Tmax and the _exptl_absorpt_correction_ values. 
;

_exptl_special_details           
; 
The crystal was mounted using polyisobutene oil on the tip of a fine glass 
fibre, which was fastened in a copper mounting pin with electrical solder. 
It was placed directly into the cold gas stream of a liquid-nitrogen based 
cryostat (Hope, 1994; Parkin & Hope, 1998). 
 
Diffraction data were collected with the crystal at 90K, which is standard 
practice in this laboratory for the majority of flash-cooled crystals. 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed-tube'
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 9.1
_diffrn_reflns_number            1334
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         5.882
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.946

_reflns_number_total             1334
_reflns_number_gt                1332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.937
_reflns_special_details          
; 
Reflections were merged by SHELXL according to the crystal 
class for the calculation of statistics and refinement. 
 
_reflns_Friedel_fraction is defined as the number of unique 
Friedel pairs measured divided by the number that would be 
possible theoretically, ignoring centric projections and 
systematic absences. 
;

_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 2006)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 2006)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  
'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)'

_refine_special_details          
; 
Refinement progress was checked using Platon (Spek, 2009) and by 
an R-tensor (Parkin, 2000). The final model was further checked 
with the IUCr utility checkCIF. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+0.0220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
Flack 'x' determined using 651 quotients [(I+)-(I-)]/[(I+)+(I-)] 
[Parsons, Flack and Wagner (2013)]. 
;
_refine_ls_abs_structure_Flack   0.010(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1334
_refine_ls_number_parameters     92
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0164
_refine_ls_wR_factor_ref         0.0461
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.098
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.43401(4) 0.16497(3) 0.29003(3) 0.01290(13) Uani 1 1 d . . . . .
N1 N 0.8355(4) 0.6921(2) 0.2824(3) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.7363(5) 0.5434(3) 0.2279(3) 0.0115(3) Uani 1 1 d . . . . .
H2A H 0.7826 0.5793 0.0772 0.014 Uiso 1 1 calc R U . . .
C3 C 0.5662(5) 0.3359(3) 0.3859(3) 0.0093(3) Uani 1 1 d . . . . .
C4 C 0.4987(5) 0.2805(3) 0.6067(3) 0.0097(3) Uani 1 1 d . . . . .
C5 C 0.5971(5) 0.4408(3) 0.6599(3) 0.0116(4) Uani 1 1 d . . . . .
H5 H 0.5483 0.4113 0.8086 0.014 Uiso 1 1 calc R U . . .
C6 C 0.7661(5) 0.6425(3) 0.4949(3) 0.0117(3) Uani 1 1 d . . . . .
H6 H 0.8351 0.7492 0.5334 0.014 Uiso 1 1 calc R U . . .
C7 C 0.3334(5) 0.0568(3) 0.7893(3) 0.0105(3) Uani 1 1 d . . . . .
O1 O 0.4028(4) -0.1122(2) 0.7849(2) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.1192(4) 0.0715(2) 0.9514(2) 0.0131(3) Uani 1 1 d . . . . .
H2 H 0.0432 -0.0552 1.0544 0.020 Uiso 1 1 calc R U . . .

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 0.0174(2) 0.01204(19) 0.01096(18) -0.00701(13) -0.00236(12) -0.00127(12)
N1 0.0142(7) 0.0092(7) 0.0101(7) -0.0026(6) 0.0003(6) -0.0005(5)
C2 0.0120(8) 0.0118(8) 0.0085(8) -0.0037(6) -0.0005(6) 0.0010(6)
C3 0.0098(7) 0.0079(8) 0.0100(7) -0.0044(6) -0.0011(6) -0.0003(6)
C4 0.0085(7) 0.0078(7) 0.0092(8) -0.0017(6) -0.0002(6) -0.0002(6)
C5 0.0152(8) 0.0106(8) 0.0079(8) -0.0038(7) -0.0015(6) 0.0003(6)
C6 0.0135(7) 0.0094(8) 0.0115(8) -0.0049(6) -0.0008(6) -0.0008(6)
C7 0.0139(8) 0.0090(8) 0.0068(7) -0.0022(6) -0.0018(6) -0.0017(6)
O1 0.0287(7) 0.0093(6) 0.0140(7) -0.0050(5) 0.0009(6) 0.0005(5)
O2 0.0185(6) 0.0078(6) 0.0076(6) -0.0014(5) 0.0036(5) -0.0042(5)

_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 C3 1.7258(18) . ?
N1 C2 1.332(2) . ?
N1 C6 1.342(2) . ?
C2 C3 1.398(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(2) . ?
C4 C5 1.398(3) . ?
C4 C7 1.511(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.211(2) . ?
C7 O2 1.315(2) . ?
O2 H2 0.8400 . ?

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
C2 N1 C6 119.05(15) . . ?
N1 C2 C3 121.98(17) . . ?
N1 C2 H2A 119.0 . . ?
C3 C2 H2A 119.0 . . ?
C4 C3 C2 119.68(16) . . ?
C4 C3 Cl1 123.46(13) . . ?
C2 C3 Cl1 116.80(14) . . ?
C3 C4 C5 117.41(15) . . ?
C3 C4 C7 123.33(15) . . ?
C5 C4 C7 119.24(15) . . ?
C6 C5 C4 119.75(16) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
N1 C6 C5 122.10(16) . . ?
N1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C7 O2 125.69(16) . . ?
O1 C7 C4 122.95(16) . . ?
O2 C7 C4 111.33(14) . . ?
C7 O2 H2 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
C6 N1 C2 C3 -0.8(3) . . . . ?
N1 C2 C3 C4 -0.4(2) . . . . ?
N1 C2 C3 Cl1 177.10(13) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
Cl1 C3 C4 C5 -175.50(14) . . . . ?
C2 C3 C4 C7 -176.97(16) . . . . ?
Cl1 C3 C4 C7 5.7(2) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
C7 C4 C5 C6 176.73(15) . . . . ?
C2 N1 C6 C5 0.5(3) . . . . ?
C4 C5 C6 N1 1.0(3) . . . . ?
C3 C4 C7 O1 36.3(3) . . . . ?
C5 C4 C7 O1 -142.46(18) . . . . ?
C3 C4 C7 O2 -145.64(16) . . . . ?
C5 C4 C7 O2 35.6(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
C5 H5 Cl1 0.95 2.93 3.8387(17) 159.9 1_556
O2 H2 N1 0.84 1.78 2.613(2) 172.9 1_446

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034

_iucr_refine_instructions_details 
; 
 
    k08179r.res created by SHELXL-2014/7 
 
 
TITL k08179 
CELL 0.71073   3.6779   6.9371   7.0372  61.6975  80.0002  89.5122 
ZERR       1   0.0001   0.0001   0.0002   0.0014   0.0012   0.0012 
LATT -1 
SFAC C  H  Cl N  O 
UNIT     6    4    1    1    2 
SIZE 0.40 0.20 0.10 
TEMP -183 
REM FORM block 
REM COLR colourless 
CONF 
BOND $H 
REM Instructions for potential hydrogen bonds 
EQIV $1 x, y, z+1 
HTAB C5 Cl1_$1 
EQIV $2 x-1, y-1, z+1 
HTAB O2 N1_$2 
WPDB 
ACTA 
LIST 4 
ACTA 
BOND $H 
FMAP 2 
PLAN 5 
L.S.  8 
OMIT  -2.0000 55 
WGHT    0.020000    0.022000 
FVAR       7.29346 
CL1   3    0.434008    0.164974    0.290025    11.00000    0.01745    0.01204 = 
         0.01096   -0.00701   -0.00236   -0.00127 
N1    4    0.835451    0.692143    0.282350    11.00000    0.01416    0.00923 = 
         0.01008   -0.00263    0.00028   -0.00052 
C2    1    0.736324    0.543386    0.227896    11.00000    0.01200    0.01176 = 
         0.00855   -0.00369   -0.00047    0.00097 
AFIX  43 
H2A   2    0.782593    0.579343    0.077239    11.00000   -1.20000 
AFIX   0 
C3    1    0.566189    0.335877    0.385851    11.00000    0.00977    0.00786 = 
         0.01004   -0.00440   -0.00111   -0.00034 
C4    1    0.498703    0.280493    0.606709    11.00000    0.00855    0.00780 = 
         0.00916   -0.00166   -0.00021   -0.00019 
C5    1    0.597147    0.440771    0.659867    11.00000    0.01519    0.01065 = 
         0.00791   -0.00376   -0.00153    0.00033 
AFIX  43 
H5    2    0.548260    0.411316    0.808635    11.00000   -1.20000 
AFIX   0 
C6    1    0.766060    0.642460    0.494924    11.00000    0.01353    0.00940 = 
         0.01147   -0.00488   -0.00078   -0.00084 
AFIX  43 
H6    2    0.835105    0.749155    0.533375    11.00000   -1.20000 
AFIX   0 
C7    1    0.333358    0.056786    0.789303    11.00000    0.01389    0.00896 = 
         0.00676   -0.00219   -0.00181   -0.00167 
O1    5    0.402805   -0.112185    0.784869    11.00000    0.02870    0.00931 = 
         0.01404   -0.00501    0.00091    0.00051 
O2    5    0.119200    0.071519    0.951432    11.00000    0.01850    0.00780 = 
         0.00764   -0.00144    0.00362   -0.00425 
AFIX 147 
H2    2    0.043228   -0.055160    1.054444    11.00000   -1.50000 
 
AFIX   0 
HKLF 4 
 
REM  k08179 
REM R1 =  0.0164 for    1332 Fo > 4sig(Fo)  and  0.0165 for all    1334 data 
REM     92 parameters refined using      3 restraints 
 
END 
 
WGHT      0.0189      0.0231 
 
REM Highest difference peak  0.215,  deepest hole -0.176,  1-sigma level  0.034 
Q1    1   0.4095  0.1623  0.6945  11.00000  0.05    0.21 
Q2    1   0.6591  0.4415  0.3007  11.00000  0.05    0.18 
Q3    1  -0.0348 -0.1732  1.1869  11.00000  0.05    0.16 
Q4    1   0.5028  0.3774  0.6200  11.00000  0.05    0.14 
Q5    1   0.6822  0.1613  0.2532  11.00000  0.05    0.14 
;
_shelx_res_checksum              7351
