# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_August1new
_database_code_depnum_ccdc_archive 'CCDC 1538319'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H3 Cl N2 O'
_chemical_formula_sum            'C4 H3 Cl N2 O'
_chemical_formula_weight         130.53

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.1254(1)
_cell_length_b                   10.6052(3)
_cell_length_c                   11.9696(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.020(2)
_cell_angle_gamma                90
_cell_volume                     520.79(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5462
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      30.49

_exptl_crystal_description       irregulat
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.613
_shelx_estimated_absorpt_T_min   0.762
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7617
_exptl_absorpt_correction_T_max  0.9191
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10674
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_max         30.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1530
_reflns_number_gt                1359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Kappa APEX 2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2015 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.1473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1530
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.11411(7) 0.40732(3) 0.11880(2) 0.03409(11) Uani 1 1 d . . . . .
O1 O 1.0466(2) 0.33497(8) 0.49926(7) 0.02954(19) Uani 1 1 d . . . . .
N2 N 0.7028(2) 0.45532(9) 0.38441(8) 0.02439(19) Uani 1 1 d . . . . .
H2A H 0.777(4) 0.5243(16) 0.4229(14) 0.039(4) Uiso 1 1 d . . . . .
N1 N 0.4819(2) 0.47729(9) 0.29441(8) 0.0251(2) Uani 1 1 d . . . . .
C1 C 0.3876(3) 0.37952(11) 0.23559(9) 0.0245(2) Uani 1 1 d . . . . .
C2 C 0.4945(3) 0.25379(11) 0.25968(9) 0.0270(2) Uani 1 1 d . . . . .
H2 H 0.4148 0.1852 0.2136 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7136(3) 0.23549(10) 0.35050(9) 0.0270(2) Uani 1 1 d . . . . .
H3 H 0.7870 0.1527 0.3701 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8357(3) 0.34170(10) 0.41766(9) 0.0238(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
Cl1 0.03419(17) 0.03949(19) 0.02715(16) -0.00128(11) -0.00359(11) 0.00603(11)
O1 0.0380(5) 0.0217(4) 0.0271(4) -0.0007(3) -0.0054(3) -0.0014(3)
N2 0.0288(5) 0.0186(4) 0.0252(4) -0.0017(3) 0.0004(4) -0.0014(3)
N1 0.0266(4) 0.0230(4) 0.0256(4) 0.0008(3) 0.0030(3) 0.0008(3)
C1 0.0254(5) 0.0258(5) 0.0226(5) 0.0000(4) 0.0039(4) 0.0008(4)
C2 0.0343(6) 0.0223(5) 0.0243(5) -0.0033(4) 0.0023(4) -0.0029(4)
C3 0.0370(6) 0.0184(5) 0.0253(5) -0.0015(4) 0.0013(4) -0.0008(4)
C4 0.0295(5) 0.0191(5) 0.0229(5) -0.0004(4) 0.0037(4) -0.0028(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 C1 1.7272(11) . ?
O1 C4 1.2399(14) . ?
N2 N1 1.3562(13) . ?
N2 C4 1.3658(14) . ?
N2 H2A 0.901(17) . ?
N1 C1 1.2902(15) . ?
C1 C2 1.4243(16) . ?
C2 C3 1.3528(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4436(15) . ?
C3 H3 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
N1 N2 C4 126.79(10) . . ?
N1 N2 H2A 115.6(11) . . ?
C4 N2 H2A 117.5(11) . . ?
C1 N1 N2 115.75(10) . . ?
N1 C1 C2 124.93(10) . . ?
N1 C1 Cl1 116.00(9) . . ?
C2 C1 Cl1 119.06(9) . . ?
C3 C2 C1 117.62(10) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 120.02(10) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
O1 C4 N2 120.49(10) . . ?
O1 C4 C3 124.67(10) . . ?
N2 C4 C3 114.83(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
C4 N2 N1 C1 0.73(16) . . . . ?
N2 N1 C1 C2 0.95(16) . . . . ?
N2 N1 C1 Cl1 -178.42(7) . . . . ?
N1 C1 C2 C3 -0.61(18) . . . . ?
Cl1 C1 C2 C3 178.74(9) . . . . ?
C1 C2 C3 C4 -1.30(17) . . . . ?
N1 N2 C4 O1 176.97(10) . . . . ?
N1 N2 C4 C3 -2.47(16) . . . . ?
C2 C3 C4 O1 -176.75(11) . . . . ?
C2 C3 C4 N2 2.66(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.901(17) 1.866(17) 2.7663(12) 177.0(16) 3_766

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL August_1_0m in P2(1)/n
CELL 0.71073   4.1254  10.6052  11.9696  90.000  96.020  90.000
ZERR    4.00   0.0001   0.0003   0.0003   0.000   0.002   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl O
UNIT 16  12  8  4  4
OMIT -3 60.2
L.S. 12
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB N2 O1_$1
EQIV $1 -x+2, -y+1, -z+1
HTAB
SIZE 0.14 0.26 0.47
WPDB
CONF
TEMP -120
WGHT    0.042600    0.147300
FVAR       0.32909
MOLE 1
CL1   4    0.114109    0.407317    0.118799    11.00000    0.03419    0.03949 =
         0.02715   -0.00128   -0.00359    0.00603
O1    5    1.046590    0.334966    0.499258    11.00000    0.03801    0.02168 =
         0.02706   -0.00071   -0.00540   -0.00138
N2    3    0.702811    0.455318    0.384405    11.00000    0.02882    0.01857 =
         0.02525   -0.00166    0.00037   -0.00138
H2A   2    0.777159    0.524255    0.422904    11.00000    0.03947
N1    3    0.481898    0.477287    0.294406    11.00000    0.02661    0.02299 =
         0.02562    0.00077    0.00297    0.00081
C1    1    0.387607    0.379515    0.235589    11.00000    0.02537    0.02577 =
         0.02256   -0.00002    0.00390    0.00082
C2    1    0.494484    0.253795    0.259680    11.00000    0.03433    0.02228 =
         0.02430   -0.00334    0.00234   -0.00293
AFIX  43
H2    2    0.414780    0.185247    0.213622    11.00000   -1.20000
AFIX   0
C3    1    0.713556    0.235489    0.350496    11.00000    0.03700    0.01839 =
         0.02528   -0.00153    0.00126   -0.00083
AFIX  43
H3    2    0.787018    0.152714    0.370080    11.00000   -1.20000
AFIX   0
C4    1    0.835743    0.341697    0.417660    11.00000    0.02954    0.01912 =
         0.02293   -0.00040    0.00370   -0.00277
HKLF 4

REM  August_1_0m in P2(1)/n
REM R1 =  0.0268 for    1359 Fo > 4sig(Fo)  and  0.0316 for all    1530 data
REM     77 parameters refined using      0 restraints

END

WGHT      0.0412      0.1506

REM Instructions for potential hydrogen bonds
HTAB N2 O1_$1

REM Highest difference peak  0.356,  deepest hole -0.347,  1-sigma level  0.047
Q1    1   0.4477  0.3202  0.2441  11.00000  0.05    0.36
Q2    1   0.2483  0.4338  0.1007  11.00000  0.05    0.34
Q3    1   0.7844  0.2896  0.3801  11.00000  0.05    0.32
Q4    1   0.5552  0.2457  0.3190  11.00000  0.05    0.31
Q5    1   0.7630  0.3952  0.3987  11.00000  0.05    0.27
;
_shelx_res_checksum              21344
####################################################################### 
# 
# 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_Johu27fin
_database_code_depnum_ccdc_archive 'CCDC 1538317'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 Cl2 N'
_chemical_formula_sum            'C7 H3 Cl2 N'
_chemical_formula_weight         172.00

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8613(1)
_cell_length_b                   11.4201(2)
_cell_length_c                   16.0731(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.936(1)
_cell_angle_gamma                90
_cell_volume                     704.97(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3372
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      33.18

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.827
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_T_max  0.8520
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16341
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.548
_diffrn_reflns_theta_max         32.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2526
_reflns_number_gt                2264
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Kappa APEX 2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.2111P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2526
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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_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 0.21734(7) 0.53574(2) 0.90408(2) 0.02866(7) Uani 1 1 d . . . . .
Cl2 Cl -0.42657(6) 0.47308(2) 0.60895(2) 0.02669(7) Uani 1 1 d . . . . .
N1 N -0.0939(2) 0.48412(7) 0.75769(5) 0.02064(14) Uani 1 1 d . . . . .
C1 C 0.0836(2) 0.43860(8) 0.82502(5) 0.01930(15) Uani 1 1 d . . . . .
C2 C 0.1682(2) 0.31993(8) 0.83486(6) 0.02015(16) Uani 1 1 d . . . . .
C3 C 0.0550(3) 0.24616(8) 0.76820(6) 0.02419(18) Uani 1 1 d . . . . .
H3 H 0.1068 0.1649 0.7715 0.029 Uiso 1 1 calc R U . . .
C4 C -0.1323(2) 0.29123(8) 0.69740(6) 0.02340(17) Uani 1 1 d . . . . .
H4 H -0.2137 0.2424 0.6516 0.028 Uiso 1 1 calc R U . . .
C5 C -0.1961(2) 0.41056(8) 0.69617(5) 0.01974(15) Uani 1 1 d . . . . .
C6 C 0.3614(3) 0.27515(9) 0.90880(6) 0.02462(17) Uani 1 1 d . . . . .
C7 C 0.5235(3) 0.23340(10) 0.96834(7) 0.0312(2) Uani 1 1 d . . . . .
H7 H 0.6531 0.2000 1.0160 0.037 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 0.03769(13) 0.02390(11) 0.02254(11) -0.00360(8) -0.00576(9) -0.00045(8)
Cl2 0.02966(12) 0.02847(12) 0.02057(11) 0.00138(8) -0.00387(8) -0.00021(8)
N1 0.0231(3) 0.0196(3) 0.0189(3) 0.0002(3) 0.0003(3) -0.0001(3)
C1 0.0199(3) 0.0189(4) 0.0189(4) -0.0003(3) 0.0016(3) -0.0019(3)
C2 0.0193(3) 0.0200(4) 0.0214(4) 0.0029(3) 0.0037(3) 0.0001(3)
C3 0.0288(4) 0.0177(4) 0.0264(4) 0.0010(3) 0.0040(3) -0.0004(3)
C4 0.0269(4) 0.0200(4) 0.0232(4) -0.0026(3) 0.0022(3) -0.0034(3)
C5 0.0196(3) 0.0213(4) 0.0183(3) 0.0008(3) 0.0018(3) -0.0018(3)
C6 0.0250(4) 0.0232(4) 0.0259(4) 0.0031(3) 0.0040(3) 0.0016(3)
C7 0.0326(5) 0.0310(5) 0.0293(5) 0.0049(4) -0.0001(4) 0.0057(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 C1 1.7252(9) . ?
Cl2 C5 1.7347(9) . ?
N1 C1 1.3258(11) . ?
N1 C5 1.3260(11) . ?
C1 C2 1.3992(13) . ?
C2 C3 1.3971(13) . ?
C2 C6 1.4308(13) . ?
C3 C4 1.3830(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3847(13) . ?
C4 H4 0.9500 . ?
C6 C7 1.1877(14) . ?
C7 H7 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
C1 N1 C5 116.68(8) . . ?
N1 C1 C2 124.54(8) . . ?
N1 C1 Cl1 116.05(7) . . ?
C2 C1 Cl1 119.40(7) . . ?
C3 C2 C1 116.51(8) . . ?
C3 C2 C6 121.10(9) . . ?
C1 C2 C6 122.39(9) . . ?
C4 C3 C2 120.15(9) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 117.07(8) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 H4 121.5 . . ?
N1 C5 C4 125.04(8) . . ?
N1 C5 Cl2 115.47(7) . . ?
C4 C5 Cl2 119.49(7) . . ?
C7 C6 C2 177.07(11) . . ?
C6 C7 H7 180.0 . . ?

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
C5 N1 C1 C2 0.04(13) . . . . ?
C5 N1 C1 Cl1 179.50(7) . . . . ?
N1 C1 C2 C3 0.04(13) . . . . ?
Cl1 C1 C2 C3 -179.40(7) . . . . ?
N1 C1 C2 C6 179.83(9) . . . . ?
Cl1 C1 C2 C6 0.39(12) . . . . ?
C1 C2 C3 C4 -0.39(13) . . . . ?
C6 C2 C3 C4 179.82(9) . . . . ?
C2 C3 C4 C5 0.63(14) . . . . ?
C1 N1 C5 C4 0.23(13) . . . . ?
C1 N1 C5 Cl2 -179.84(6) . . . . ?
C3 C4 C5 N1 -0.57(14) . . . . ?
C3 C4 C5 Cl2 179.50(7) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL Johu27new in P2(1)/n
CELL 0.71073   3.8613  11.4201  16.0731  90.000  95.936  90.000
ZERR    4.00   0.0001   0.0002   0.0003   0.000   0.001   0.000
LATT 1
SYMM 0.5-X, 0.5+Y, 0.5-Z
SFAC C  H  N  Cl
UNIT 28  12  4  8
OMIT -3 64.8
L.S. 15
ACTA
BOND $H
FMAP 2
PLAN 5
SIZE 0.450 0.210 0.200
CONF
WPDB
HTAB
TEMP -120
WGHT    0.029300    0.211100
FVAR       0.24095
MOLE 1
CL1   4    0.217340    0.535737    0.904079    11.00000    0.03769    0.02390 =
         0.02254   -0.00360   -0.00576   -0.00045
CL2   4   -0.426567    0.473085    0.608954    11.00000    0.02966    0.02847 =
         0.02057    0.00138   -0.00387   -0.00021
N1    3   -0.093942    0.484124    0.757689    11.00000    0.02307    0.01957 =
         0.01890    0.00022    0.00027   -0.00009
C1    1    0.083577    0.438601    0.825020    11.00000    0.01992    0.01894 =
         0.01894   -0.00027    0.00160   -0.00187
C2    1    0.168212    0.319927    0.834862    11.00000    0.01932    0.02005 =
         0.02140    0.00287    0.00366    0.00009
C3    1    0.055000    0.246164    0.768203    11.00000    0.02875    0.01770 =
         0.02635    0.00099    0.00403   -0.00039
AFIX  43
H3    2    0.106791    0.164871    0.771517    11.00000   -1.20000
AFIX   0
C4    1   -0.132306    0.291226    0.697402    11.00000    0.02692    0.02003 =
         0.02316   -0.00265    0.00215   -0.00338
AFIX  43
H4    2   -0.213655    0.242449    0.651626    11.00000   -1.20000
AFIX   0
C5    1   -0.196053    0.410563    0.696171    11.00000    0.01963    0.02128 =
         0.01827    0.00080    0.00179   -0.00179
C6    1    0.361447    0.275154    0.908801    11.00000    0.02499    0.02323 =
         0.02594    0.00310    0.00399    0.00155
C7    1    0.523466    0.233400    0.968336    11.00000    0.03261    0.03103 =
         0.02932    0.00489   -0.00012    0.00569
AFIX 163
H7    2    0.653059    0.200002    1.015957    11.00000   -1.20000
AFIX   0
HKLF 4

REM  Johu27new in P2(1)/n
REM R1 =  0.0238 for    2264 Fo > 4sig(Fo)  and  0.0280 for all    2526 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0291      0.2111

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.398,  deepest hole -0.213,  1-sigma level  0.048
Q1    1   0.1241  0.2840  0.8028  11.00000  0.05    0.40
Q2    1   0.1241  0.3774  0.8360  11.00000  0.05    0.37
Q3    1  -0.1817  0.3511  0.6957  11.00000  0.05    0.35
Q4    1   0.0084  0.4575  0.7862  11.00000  0.05    0.35
Q5    1  -0.0518  0.2735  0.7354  11.00000  0.05    0.33
;
_shelx_res_checksum              277
####################################################################### 
# 
# 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_Hoehne1fin
_database_code_depnum_ccdc_archive 'CCDC 1538316'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H2 Cl2 I N'
_chemical_formula_sum            'C5 H2 Cl2 I N'
_chemical_formula_weight         273.88

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   13.4092(4)
_cell_length_b                   6.7578(2)
_cell_length_c                   7.9577(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     721.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8852
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      40.34

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.523
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.084
_shelx_estimated_absorpt_T_min   0.330
_shelx_estimated_absorpt_T_max   0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3302
_exptl_absorpt_correction_T_max  0.5160
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13425
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         35.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1734
_reflns_number_gt                1630
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Kappa APEX 2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0155P)²+0.3969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1734
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0168
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0359
_refine_ls_wR_factor_gt          0.0352
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.003
_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
C1 C 0.16989(12) 0.7500 0.55576(18) 0.0112(2) Uani 1 2 d S T P . .
C2 C 0.17624(12) 0.7500 0.72994(19) 0.0127(3) Uani 1 2 d S T P . .
H2 H 0.2375 0.7500 0.7847 0.015 Uiso 1 2 calc R U P . .
C3 C 0.08690(11) 0.7500 0.81909(19) 0.0117(3) Uani 1 2 d S T P . .
C4 C -0.00319(12) 0.7500 0.73225(19) 0.0120(3) Uani 1 2 d S T P . .
H4 H -0.0640 0.7500 0.7884 0.014 Uiso 1 2 calc R U P . .
C5 C 0.00183(12) 0.7500 0.55775(18) 0.0108(2) Uani 1 2 d S T P . .
Cl1 Cl 0.27862(3) 0.7500 0.43898(5) 0.01617(7) Uani 1 2 d S T P . .
Cl2 Cl -0.10835(3) 0.7500 0.44398(5) 0.01373(7) Uani 1 2 d S T P . .
I1 I 0.08697(2) 0.7500 1.08062(2) 0.01254(3) Uani 1 2 d S T P . .
N1 N 0.08537(10) 0.7500 0.46839(18) 0.0115(2) Uani 1 2 d S T P . .

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
C1 0.0114(6) 0.0142(6) 0.0081(6) 0.000 0.0008(5) 0.000
C2 0.0135(7) 0.0163(6) 0.0083(6) 0.000 -0.0018(5) 0.000
C3 0.0147(7) 0.0151(6) 0.0051(6) 0.000 -0.0010(4) 0.000
C4 0.0132(7) 0.0156(6) 0.0072(6) 0.000 0.0009(5) 0.000
C5 0.0116(6) 0.0118(6) 0.0089(6) 0.000 -0.0016(4) 0.000
Cl1 0.01214(16) 0.02616(19) 0.01021(15) 0.000 0.00275(11) 0.000
Cl2 0.01227(16) 0.01773(16) 0.01119(15) 0.000 -0.00362(12) 0.000
I1 0.01554(5) 0.01626(5) 0.00581(5) 0.000 -0.00003(3) 0.000
N1 0.0123(6) 0.0135(5) 0.0088(5) 0.000 0.0000(4) 0.000

_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
C1 N1 1.330(2) . ?
C1 C2 1.389(2) . ?
C1 Cl1 1.7289(16) . ?
C2 C3 1.392(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.392(2) . ?
C3 I1 2.0811(15) . ?
C4 C5 1.390(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.327(2) . ?
C5 Cl2 1.7328(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
N1 C1 C2 125.05(15) . . ?
N1 C1 Cl1 115.96(11) . . ?
C2 C1 Cl1 118.99(12) . . ?
C1 C2 C3 117.11(14) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C4 C3 C2 119.59(14) . . ?
C4 C3 I1 119.80(11) . . ?
C2 C3 I1 120.60(11) . . ?
C5 C4 C3 117.00(14) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
N1 C5 C4 125.18(15) . . ?
N1 C5 Cl2 116.09(11) . . ?
C4 C5 Cl2 118.72(12) . . ?
C5 N1 C1 116.06(14) . . ?

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
N1 C1 C2 C3 0.000(0) . . . . ?
Cl1 C1 C2 C3 180.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C1 C2 C3 I1 180.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
I1 C3 C4 C5 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C5 Cl2 180.000(0) . . . . ?
C4 C5 N1 C1 0.000(0) . . . . ?
Cl2 C5 N1 C1 180.000(0) . . . . ?
C2 C1 N1 C5 0.000(0) . . . . ?
Cl1 C1 N1 C5 180.000(0) . . . . ?

_refine_diff_density_max         0.763
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL Hoehne1new in Pnma
CELL 0.71073  13.4092   6.7578   7.9577  90.000  90.000  90.000
ZERR    4.00   0.0004   0.0002   0.0002   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C  H  N  Cl I
UNIT 20  8  4  8  4
OMIT 0 2 0
OMIT -3 70.8
L.S. 12
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB C2 Cl2_$1
CONF
WPDB
SIZE 0.150 0.280 0.280
HTAB
EQIV $1 x+1/2, y, -z+3/2
HTAB C2 Cl2_$1
HTAB C2 Cl2_$1
TEMP 23.000
WGHT    0.015500    0.396900
FVAR       0.08899
C1    1    0.169888    0.750000    0.555760    10.50000    0.01140    0.01421 =
         0.00808    0.00000    0.00084    0.00000
C2    1    0.176243    0.750000    0.729939    10.50000    0.01347    0.01626 =
         0.00828    0.00000   -0.00178    0.00000
AFIX  43
H2    2    0.237523    0.750000    0.784670    10.50000   -1.20000
AFIX   0
C3    1    0.086895    0.750000    0.819094    10.50000    0.01474    0.01512 =
         0.00512    0.00000   -0.00099    0.00000
C4    1   -0.003191    0.750000    0.732251    10.50000    0.01315    0.01564 =
         0.00723    0.00000    0.00085    0.00000
AFIX  43
H4    2   -0.064011    0.750000    0.788419    10.50000   -1.20000
AFIX   0
C5    1    0.001830    0.750000    0.557752    10.50000    0.01156    0.01179 =
         0.00894    0.00000   -0.00157    0.00000
CL1   4    0.278617    0.750000    0.438983    10.50000    0.01214    0.02616 =
         0.01021    0.00000    0.00275    0.00000
CL2   4   -0.108349    0.750000    0.443977    10.50000    0.01227    0.01773 =
         0.01119    0.00000   -0.00362    0.00000
I1    5    0.086974    0.750000    1.080615    10.50000    0.01554    0.01626 =
         0.00581    0.00000   -0.00003    0.00000
N1    3    0.085368    0.750000    0.468390    10.50000    0.01228    0.01346 =
         0.00875    0.00000   -0.00004    0.00000
HKLF 4

REM  Hoehne1new in Pnma
REM R1 =  0.0149 for    1630 Fo > 4sig(Fo)  and  0.0168 for all    1734 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0155      0.3961

REM Instructions for potential hydrogen bonds
HTAB C2 Cl2_$1

REM Highest difference peak  0.763,  deepest hole -0.583,  1-sigma level  0.106
Q1    1   0.2377  0.7500  0.4178  10.50000  0.05    0.76
Q2    1   0.0046  0.7500  0.6362  10.50000  0.05    0.60
Q3    1   0.1729  0.7500  0.6442  10.50000  0.05    0.55
Q4    1   0.1244  0.7500  0.5259  10.50000  0.05    0.54
Q5    1   0.1290  0.7500  0.7713  10.50000  0.05    0.53
;
_shelx_res_checksum              686
####################################################################### 
# 
# 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_koepp1pnma2
_database_code_depnum_ccdc_archive 'CCDC 1538318'
_audit_update_record             
;
2017-03-16 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 Cl I N2'
_chemical_formula_sum            'C4 H2 Cl I N2'
_chemical_formula_weight         240.43

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   14.8774(3)
_cell_length_b                   6.7419(2)
_cell_length_c                   6.1893(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     620.80(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7333
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      37.90

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.572
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    5.473
_shelx_estimated_absorpt_T_min   0.171
_shelx_estimated_absorpt_T_max   0.320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1706
_exptl_absorpt_correction_T_max  0.3196
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10081
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.738
_diffrn_reflns_theta_max         34.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1366
_reflns_number_gt                1201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Kappa APEX 2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0199P)²+0.5996P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1366
_refine_ls_number_parameters     49
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0488
_refine_ls_wR_factor_gt          0.0463
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.152
_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_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
I1 I 0.24948(2) 0.2500 0.71401(2) 0.01983(5) Uani 1 2 d S T P . .
Cl1 Cl -0.10376(4) 0.2500 1.31580(10) 0.02534(12) Uani 1 2 d S T P . .
N1 N -0.02605(13) 0.2500 0.9400(3) 0.0206(4) Uani 1 2 d S T P . .
N2 N 0.06760(13) 0.2500 1.2527(3) 0.0193(4) Uani 1 2 d S T P . .
C1 C 0.13337(14) 0.2500 0.9019(3) 0.0163(4) Uani 1 2 d S T P . .
C2 C 0.04773(16) 0.2500 0.8140(4) 0.0199(4) Uani 1 2 d S T P . .
H2 H 0.0410 0.2500 0.6646 0.024 Uiso 1 2 calc R U P . .
C3 C -0.01007(14) 0.2500 1.1489(4) 0.0174(4) Uani 1 2 d S T P . .
C4 C 0.14025(14) 0.2500 1.1250(4) 0.0184(4) Uani 1 2 d S T P . .
H4 H 0.1970 0.2500 1.1881 0.022 Uiso 1 2 calc R U P . .

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
I1 0.01839(8) 0.02463(9) 0.01648(8) 0.000 0.00410(4) 0.000
Cl1 0.0166(2) 0.0344(3) 0.0251(3) 0.000 0.00590(19) 0.000
N1 0.0184(8) 0.0258(10) 0.0175(9) 0.000 -0.0024(7) 0.000
N2 0.0163(8) 0.0270(10) 0.0145(7) 0.000 0.0011(7) 0.000
C1 0.0165(8) 0.0182(10) 0.0140(8) 0.000 0.0011(7) 0.000
C2 0.0201(9) 0.0262(11) 0.0136(9) 0.000 -0.0029(7) 0.000
C3 0.0157(8) 0.0181(10) 0.0183(10) 0.000 0.0015(7) 0.000
C4 0.0151(8) 0.0254(11) 0.0147(9) 0.000 -0.0012(7) 0.000

_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
I1 C1 2.082(2) . ?
Cl1 C3 1.735(2) . ?
N1 C3 1.315(3) . ?
N1 C2 1.346(3) . ?
N2 C3 1.322(3) . ?
N2 C4 1.339(3) . ?
C1 C4 1.385(3) . ?
C1 C2 1.386(3) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 114.98(19) . . ?
C3 N2 C4 114.8(2) . . ?
C4 C1 C2 117.4(2) . . ?
C4 C1 I1 119.70(16) . . ?
C2 C1 I1 122.92(16) . . ?
N1 C2 C1 121.5(2) . . ?
N1 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N1 C3 N2 129.5(2) . . ?
N1 C3 Cl1 116.12(16) . . ?
N2 C3 Cl1 114.41(17) . . ?
N2 C4 C1 121.9(2) . . ?
N2 C4 H4 119.0 . . ?
C1 C4 H4 119.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 C1 0.000(1) . . . . ?
C4 C1 C2 N1 0.000(1) . . . . ?
I1 C1 C2 N1 180.000(0) . . . . ?
C2 N1 C3 N2 0.000(1) . . . . ?
C2 N1 C3 Cl1 180.000(0) . . . . ?
C4 N2 C3 N1 0.000(1) . . . . ?
C4 N2 C3 Cl1 180.000(0) . . . . ?
C3 N2 C4 C1 0.000(1) . . . . ?
C2 C1 C4 N2 0.000(1) . . . . ?
I1 C1 C4 N2 180.000(0) . . . . ?

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
C2 H2 N2 0.93 2.58 3.487(3) 165.1 1_554

_refine_diff_density_max         0.836
_refine_diff_density_min         -1.702
_refine_diff_density_rms         0.146

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL koepp1pnma2 in Pnma
CELL 0.71073  14.87740   6.74190   6.18930  90.0000  90.0000  90.0000
ZERR    4.00   0.00030   0.00020   0.00010   0.0000   0.0000   0.0000
LATT 1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, -Z
SYMM 0.5+X, 0.5-Y, 0.5-Z
SFAC C  H  N  Cl I
UNIT 16  8  8  4  4
OMIT 7 1 1
OMIT 0 2 0
OMIT -3 68.2
L.S. 14
ACTA
BOND $H
FMAP 2
PLAN 5
HTAB C4 Cl1_$2
EQIV $2 x+1/2, y, -z+1/2
HTAB C2 N2_$1
EQIV $1 x, y, z-1
CONF
WPDB
HTAB
SIZE 0.27 0.40 0.50
TEMP 23
WGHT    0.019900    0.599600
FVAR       0.11037
MOLE 1
I1    5    0.249483    0.250000    0.714013    10.50000    0.01839    0.02463 =
         0.01648    0.00000    0.00410    0.00000
CL1   4   -0.103759    0.250000    1.315803    10.50000    0.01656    0.03438 =
         0.02507    0.00000    0.00590    0.00000
N1    3   -0.026049    0.250000    0.939974    10.50000    0.01842    0.02582 =
         0.01747    0.00000   -0.00242    0.00000
N2    3    0.067601    0.250000    1.252663    10.50000    0.01626    0.02704 =
         0.01447    0.00000    0.00111    0.00000
C1    1    0.133366    0.250000    0.901908    10.50000    0.01654    0.01822 =
         0.01400    0.00000    0.00105    0.00000
C2    1    0.047726    0.250000    0.813963    10.50000    0.02008    0.02616 =
         0.01356    0.00000   -0.00292    0.00000
AFIX  43
H2    2    0.041048    0.250000    0.664564    10.50000   -1.20000
AFIX   0
C3    1   -0.010072    0.250000    1.148950    10.50000    0.01573    0.01811 =
         0.01830    0.00000    0.00145    0.00000
C4    1    0.140253    0.250000    1.125036    10.50000    0.01513    0.02538 =
         0.01471    0.00000   -0.00124    0.00000
AFIX  43
H4    2    0.197000    0.250000    1.188060    10.50000   -1.20000
AFIX   0
HKLF 4

REM  koepp1pnma2 in Pnma
REM R1 =  0.0188 for    1201 Fo > 4sig(Fo)  and  0.0234 for all    1366 data
REM     49 parameters refined using      0 restraints

END

WGHT      0.0187      0.6263

REM Instructions for potential hydrogen bonds
HTAB C2 N2_$1
EQIV $3 x+1/2, y, -z+5/2
HTAB C4 Cl1_$3

REM Highest difference peak  0.836,  deepest hole -1.702,  1-sigma level  0.146
Q1    1   0.2484  0.2500  0.5745  10.50000  0.05    0.84
Q2    1   0.0913  0.2500  0.8770  10.50000  0.05    0.73
Q3    1   0.1358  0.2500  1.0093  10.50000  0.05    0.73
Q4    1   0.2497  0.2500  0.4455  10.50000  0.05    0.49
Q5    1  -0.0914  0.2500  0.9051  10.50000  0.05    0.48
;
_shelx_res_checksum              41964
