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

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

data_15145b26diCl
_database_code_depnum_ccdc_archive 'CCDC 1879702'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,6-dichlorobenzonitrile-N-oxide
_chemical_name_common            '2,6-dichlorobenzonitrile oxide'
_chemical_melting_point          348-350K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl2 N O'
_chemical_formula_weight         188.00

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   3.9611(2)
_cell_length_b                   13.3377(5)
_cell_length_c                   14.4800(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.848(2)
_cell_angle_gamma                90
_cell_volume                     757.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4939
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      74.50

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.4212
_exptl_transmission_factor_max   0.7538
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    7.172
_shelx_estimated_absorpt_T_min   0.267
_shelx_estimated_absorpt_T_max   0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4212
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS-2014 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'ImuS micro-focus'
_diffrn_measurement_device_type  'Bruker-AXS D8 Venture PHOTON-II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6061
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.527
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1535
_reflns_number_gt                1416
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Allen et al, 2004)'
_computing_publication_material  'Bruker SHELXTL enCIFer (Allen et al, 2004)'
_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)+(0.0499P)²+0.5840P] 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         1535
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.86812(15) 0.40063(4) 0.79965(3) 0.02934(18) Uani 1 1 d . . . . .
Cl2 Cl 0.72597(14) 0.10194(3) 0.54640(4) 0.02733(18) Uani 1 1 d . . . . .
C1 C 0.8135(5) 0.25732(14) 0.66664(12) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.9251(5) 0.35489(14) 0.69115(12) 0.0173(4) Uani 1 1 d . . . . .
C3 C 1.0783(5) 0.41401(14) 0.63074(14) 0.0198(4) Uani 1 1 d . . . . .
H3 H 1.1531 0.4798 0.6484 0.024 Uiso 1 1 calc R U . . .
C4 C 1.1218(5) 0.37619(14) 0.54386(14) 0.0187(4) Uani 1 1 d . . . . .
H4 H 1.2272 0.4167 0.5020 0.022 Uiso 1 1 calc R U . . .
C5 C 1.0142(5) 0.28032(14) 0.51695(12) 0.0181(4) Uani 1 1 d . . . . .
H5 H 1.0447 0.2553 0.4572 0.022 Uiso 1 1 calc R U . . .
C6 C 0.8616(5) 0.22164(13) 0.57847(12) 0.0164(4) Uani 1 1 d . . . . .
C7 C 0.6509(5) 0.19759(15) 0.72908(14) 0.0215(4) Uani 1 1 d . . . . .
N1 N 0.5170(4) 0.15921(12) 0.78480(11) 0.0192(4) Uani 1 1 d . . . . .
O1 O 0.3737(4) 0.11640(12) 0.84353(11) 0.0309(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 0.0403(3) 0.0330(3) 0.0148(3) -0.00750(17) 0.0040(2) 0.0025(2)
Cl2 0.0341(3) 0.0156(3) 0.0318(3) -0.00542(17) 0.0028(2) -0.00317(17)
C1 0.0136(9) 0.0183(9) 0.0153(8) 0.0052(7) 0.0003(7) 0.0036(7)
C2 0.0185(9) 0.0198(9) 0.0126(8) -0.0017(7) -0.0016(7) 0.0037(7)
C3 0.0216(10) 0.0139(8) 0.0231(10) -0.0005(7) 0.0002(7) 0.0001(7)
C4 0.0194(10) 0.0178(9) 0.0194(9) 0.0061(7) 0.0041(7) 0.0023(7)
C5 0.0201(9) 0.0202(9) 0.0138(8) -0.0004(7) 0.0022(7) 0.0058(7)
C6 0.0173(9) 0.0139(8) 0.0169(9) -0.0008(7) -0.0016(7) 0.0035(7)
C7 0.0204(10) 0.0228(9) 0.0212(9) 0.0064(8) 0.0029(8) 0.0035(7)
N1 0.0207(8) 0.0181(8) 0.0191(8) 0.0013(6) 0.0044(6) 0.0019(6)
O1 0.0351(9) 0.0325(8) 0.0284(8) 0.0102(6) 0.0164(7) -0.0005(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 C2 1.7288(18) . ?
Cl2 C6 1.7277(19) . ?
C1 C6 1.400(3) . ?
C1 C2 1.404(3) . ?
C1 C7 1.423(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.95 . ?
C4 C5 1.387(3) . ?
C4 H4 0.95 . ?
C5 C6 1.385(3) . ?
C5 H5 0.95 . ?
C7 N1 1.145(3) . ?
N1 O1 1.226(2) . ?

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
C6 C1 C2 117.92(17) . . ?
C6 C1 C7 121.26(17) . . ?
C2 C1 C7 120.81(17) . . ?
C3 C2 C1 121.36(17) . . ?
C3 C2 Cl1 119.88(15) . . ?
C1 C2 Cl1 118.75(15) . . ?
C2 C3 C4 119.16(17) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.23(18) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 118.99(17) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.34(17) . . ?
C5 C6 Cl2 119.75(14) . . ?
C1 C6 Cl2 118.90(14) . . ?
N1 C7 C1 172.3(2) . . ?
C7 N1 O1 178.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

C7 C1 C2 C3 -179.01(18) . . . . ?
C6 C1 C2 Cl1 179.94(14) . . . . ?
C7 C1 C2 Cl1 1.1(2) . . . . ?
Cl1 C2 C3 C4 -179.94(15) . . . . ?
C4 C5 C6 Cl2 -179.96(14) . . . . ?
C7 C1 C6 C5 178.81(17) . . . . ?
C2 C1 C6 Cl2 -179.87(13) . . . . ?
C7 C1 C6 Cl2 -1.0(2) . . . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.077

_shelx_res_file                  
;

    15145b.res created by SHELXL-2014/7


TITL 15145a in P2(1)/c
CELL 1.54178 3.9611 13.3377 14.4800 90.000 97.848 90.000
ZERR 4.00 0.0002 0.0005 0.0005 0.000 0.002 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C  H  N  O  Cl
UNIT 28 12 4 4 8
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 5
CONF
SIZE 0.220 0.230 0.250
TEMP -150.150
WGHT    0.049900    0.584000
FVAR       0.17810
CL1   5    0.868124    0.400631    0.799651    11.00000    0.04027    0.03296 =
         0.01485   -0.00750    0.00397    0.00249
CL2   5    0.725974    0.101945    0.546400    11.00000    0.03412    0.01555 =
         0.03184   -0.00542    0.00280   -0.00317
C1    1    0.813538    0.257316    0.666640    11.00000    0.01357    0.01834 =
         0.01525    0.00519    0.00027    0.00362
C2    1    0.925118    0.354887    0.691146    11.00000    0.01851    0.01983 =
         0.01258   -0.00171   -0.00163    0.00374
C3    1    1.078256    0.414008    0.630741    11.00000    0.02161    0.01389 =
         0.02311   -0.00048    0.00021    0.00015
AFIX  43
H3    2    1.153068    0.479811    0.648354    11.00000   -1.20000
AFIX   0
C4    1    1.121772    0.376189    0.543862    11.00000    0.01943    0.01781 =
         0.01942    0.00612    0.00414    0.00231
AFIX  43
H4    2    1.227206    0.416732    0.502046    11.00000   -1.20000
AFIX   0
C5    1    1.014219    0.280324    0.516953    11.00000    0.02012    0.02018 =
         0.01383   -0.00041    0.00224    0.00575
AFIX  43
H5    2    1.044733    0.255278    0.457235    11.00000   -1.20000
AFIX   0
C6    1    0.861614    0.221639    0.578475    11.00000    0.01734    0.01385 =
         0.01689   -0.00082   -0.00161    0.00347
C7    1    0.650933    0.197589    0.729082    11.00000    0.02045    0.02277 =
         0.02119    0.00642    0.00287    0.00347
N1    3    0.517006    0.159211    0.784799    11.00000    0.02075    0.01812 =
         0.01908    0.00134    0.00437    0.00192
O1    4    0.373671    0.116398    0.843532    11.00000    0.03512    0.03254 =
         0.02837    0.01016    0.01636   -0.00049
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  15145a in P2(1)/c
REM R1 =  0.0368 for    1416 Fo > 4sig(Fo)  and  0.0396 for all    1535 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0499      0.5840

REM Highest difference peak  0.290,  deepest hole -0.460,  1-sigma level  0.077
Q1    1   1.0310  0.2402  0.5606  11.00000  0.05    0.29
Q2    1   0.9177  0.3002  0.6817  11.00000  0.05    0.29
Q3    1   0.8699  0.2616  0.5402  11.00000  0.05    0.27
Q4    1   0.9076  0.3836  0.6427  11.00000  0.05    0.26
Q5    1   0.8816  0.2377  0.6304  11.00000  0.05    0.24
;
_shelx_res_checksum              82760

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_15150a
_database_code_depnum_ccdc_archive 'CCDC 1879704'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        3-bromobenzonitrile-N-oxide
_chemical_name_common            '3-bromobenzonitrile oxide'
_chemical_melting_point          '372-377 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Br N O'
_chemical_formula_weight         198.02

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   25.671(15)
_cell_length_b                   3.903(2)
_cell_length_c                   14.123(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.068(6)
_cell_angle_gamma                90
_cell_volume                     1359.9(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      26.18

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.4301
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    5.962
_shelx_estimated_absorpt_T_min   0.154
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4301
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5423
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.651
_diffrn_reflns_theta_max         26.333
_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             1379
_reflns_number_gt                980
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Allen et al, 2004)'
_computing_publication_material  'Bruker SHELXTL enCIFer (Allen et al, 2004)'
_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)+(0.0508P)²] 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         1379
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Br1 Br 0.29862(2) 0.18826(14) 0.11199(4) 0.0436(2) Uani 1 1 d . . . . .
C1 C 0.41638(19) 0.5683(13) 0.3458(4) 0.0375(12) Uani 1 1 d . . . . .
C2 C 0.38723(19) 0.4818(13) 0.2520(4) 0.0356(11) Uani 1 1 d . . . . .
H2 H 0.4004 0.5350 0.1971 0.043 Uiso 1 1 calc R U . . .
C3 C 0.3389(2) 0.3176(12) 0.2393(4) 0.0338(11) Uani 1 1 d . . . . .
C4 C 0.3193(2) 0.2356(12) 0.3176(4) 0.0390(13) Uani 1 1 d . . . . .
H4 H 0.2859 0.1169 0.3076 0.047 Uiso 1 1 calc R U . . .
C5 C 0.3489(2) 0.3286(14) 0.4102(4) 0.0459(14) Uani 1 1 d . . . . .
H5 H 0.3356 0.2759 0.4648 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3968(2) 0.4937(15) 0.4255(4) 0.0442(13) Uani 1 1 d . . . . .
H6 H 0.4167 0.5581 0.4902 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4659(2) 0.7456(13) 0.3593(4) 0.0441(13) Uani 1 1 d . . . . .
N1 N 0.50580(18) 0.8825(11) 0.3666(3) 0.0414(11) Uani 1 1 d . . . . .
O1 O 0.54879(14) 1.0278(11) 0.3740(3) 0.0560(11) 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
Br1 0.0457(3) 0.0429(4) 0.0383(4) -0.0057(2) 0.0050(2) -0.0012(2)
C1 0.034(3) 0.030(3) 0.048(3) 0.001(2) 0.011(2) 0.005(2)
C2 0.039(3) 0.031(3) 0.040(3) 0.001(2) 0.016(2) 0.004(2)
C3 0.039(3) 0.025(2) 0.037(3) 0.001(2) 0.010(2) 0.003(2)
C4 0.044(3) 0.035(3) 0.043(3) 0.000(2) 0.022(3) -0.001(2)
C5 0.065(4) 0.042(3) 0.040(3) 0.005(2) 0.028(3) 0.003(3)
C6 0.055(4) 0.043(3) 0.031(3) 0.001(2) 0.005(3) 0.007(3)
C7 0.044(3) 0.041(4) 0.044(3) 0.002(2) 0.006(3) 0.008(2)
N1 0.036(3) 0.045(3) 0.039(3) -0.003(2) 0.005(2) -0.002(2)
O1 0.046(2) 0.064(3) 0.056(3) -0.010(2) 0.011(2) -0.017(2)

_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
Br1 C3 1.878(5) . ?
C1 C2 1.372(7) . ?
C1 C6 1.385(7) . ?
C1 C7 1.413(8) . ?
C2 C3 1.363(7) . ?
C2 H2 0.95 . ?
C3 C4 1.373(7) . ?
C4 C5 1.367(8) . ?
C4 H4 0.95 . ?
C5 C6 1.350(8) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.134(7) . ?
N1 O1 1.219(5) . ?

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 C1 C6 120.6(5) . . ?
C2 C1 C7 118.7(5) . . ?
C6 C1 C7 120.6(5) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 Br1 119.5(4) . . ?
C4 C3 Br1 118.7(4) . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 121.4(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.3(5) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C1 177.2(6) . . ?
C7 N1 O1 179.5(6) . . ?

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

C7 C1 C2 C3 -178.6(5) . . . . ?
C1 C2 C3 Br1 -178.9(4) . . . . ?
Br1 C3 C4 C5 179.7(4) . . . . ?
C7 C1 C6 C5 179.0(5) . . . . ?

_refine_diff_density_max         0.726
_refine_diff_density_min         -0.943
_refine_diff_density_rms         0.119

_shelx_res_file                  
;

    15150a.res created by SHELXL-2014/7


TITL 15150a in C2/c
CELL 0.71073 25.6714 3.9034 14.1232 90.000 106.068 90.000
ZERR 8.00 0.0149 0.0023 0.0081 0.000 0.006 0.000
LATT 7
SYMM -x, y, -z+1/2
SFAC C  H  N  O  Br
UNIT 56 32 8 8 8
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 8
ACTA
BOND $H
FMAP 2
PLAN 10
CONF
SIZE 0.030 0.140 0.500
TEMP -100
WGHT    0.050800
FVAR       0.10191
BR1   5    0.298623    0.188263    0.111994    11.00000    0.04573    0.04288 =
         0.03834   -0.00571    0.00499   -0.00124
C1    1    0.416381    0.568258    0.345812    11.00000    0.03412    0.03019 =
         0.04777    0.00063    0.01050    0.00473
C2    1    0.387233    0.481788    0.251966    11.00000    0.03873    0.03069 =
         0.04044    0.00101    0.01609    0.00392
AFIX  43
H2    2    0.400398    0.535047    0.197115    11.00000   -1.20000
AFIX   0
C3    1    0.338920    0.317596    0.239303    11.00000    0.03935    0.02460 =
         0.03698    0.00078    0.00992    0.00342
C4    1    0.319314    0.235587    0.317581    11.00000    0.04448    0.03529 =
         0.04306   -0.00049    0.02164   -0.00085
AFIX  43
H4    2    0.285922    0.116885    0.307615    11.00000   -1.20000
AFIX   0
C5    1    0.348918    0.328576    0.410163    11.00000    0.06457    0.04167 =
         0.03957    0.00496    0.02771    0.00304
AFIX  43
H5    2    0.335559    0.275908    0.464829    11.00000   -1.20000
AFIX   0
C6    1    0.396753    0.493735    0.425511    11.00000    0.05490    0.04267 =
         0.03122    0.00147    0.00535    0.00703
AFIX  43
H6    2    0.416730    0.558124    0.490246    11.00000   -1.20000
AFIX   0
C7    1    0.465910    0.745576    0.359322    11.00000    0.04368    0.04057 =
         0.04422    0.00171    0.00598    0.00761
N1    3    0.505800    0.882495    0.366565    11.00000    0.03598    0.04532 =
         0.03947   -0.00324    0.00495   -0.00235
O1    4    0.548794    1.027846    0.373989    11.00000    0.04555    0.06439 =
         0.05646   -0.00950    0.01131   -0.01696
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  15150a in C2/c
REM R1 =  0.0434 for     980 Fo > 4sig(Fo)  and  0.0693 for all    1379 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0500      0.0000

REM Highest difference peak  0.726,  deepest hole -0.943,  1-sigma level  0.119
Q1    1   0.2902  0.1784  0.0041  11.00000  0.05    0.73
Q2    1   0.2989 -0.1293  0.1157  11.00000  0.05    0.60
Q3    1   0.3090  0.1503  0.2175  11.00000  0.05    0.55
Q4    1   0.3009  0.4769  0.1161  11.00000  0.05    0.45
Q5    1   0.2407  0.3472  0.0571  11.00000  0.05    0.41
Q6    1   0.3416  0.1751  0.0460  11.00000  0.05    0.37
Q7    1   0.3381  0.1840  0.0704  11.00000  0.05    0.36
Q8    1   0.3159  0.4069  0.2626  11.00000  0.05    0.33
Q9    1   0.3029  0.3006  0.4372  11.00000  0.05    0.33
Q10   1   0.3178 -0.1238  0.2568  11.00000  0.05    0.32
;
_shelx_res_checksum              65040

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_15176a23diCl
_database_code_depnum_ccdc_archive 'CCDC 1879703'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2,3-dichlorobenzonitrile-N-oxide
_chemical_name_common            '2,3-dichlorobenzonitrile oxide'
_chemical_melting_point          '383-388 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl2 N O'
_chemical_formula_weight         188.00

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'
O O 0.0106 0.0060 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   3.7857(10)
_cell_length_b                   12.616(3)
_cell_length_c                   15.632(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.847(4)
_cell_angle_gamma                90
_cell_volume                     744.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    608
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.55

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   0.5761
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.800
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1712
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.076
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1712
_reflns_number_gt                1623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Allen et al, 2004)'
_computing_publication_material  'Bruker SHELXTL enCIFer (Allen et al, 2004)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+0.2238P] 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         1712
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.0047(4) 0.20434(11) 0.09664(10) 0.0250(3) Uani 1 1 d . . . . .
C2 C 0.1619(4) 0.30522(12) 0.09379(9) 0.0241(3) Uani 1 1 d . . . . .
C3 C 0.2521(4) 0.35764(11) 0.17009(10) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.1906(5) 0.31193(12) 0.24832(10) 0.0280(3) Uani 1 1 d . . . . .
H4 H 0.2519 0.3489 0.3001 0.034 Uiso 1 1 calc R U . . .
C5 C 0.0390(5) 0.21182(13) 0.25071(10) 0.0297(4) Uani 1 1 d . . . . .
H5 H -0.0021 0.1804 0.3043 0.036 Uiso 1 1 calc R U . . .
C6 C -0.0524(5) 0.15759(12) 0.17555(10) 0.0281(3) Uani 1 1 d . . . . .
H6 H -0.1537 0.0888 0.1776 0.034 Uiso 1 1 calc R U . . .
C7 C -0.1043(5) 0.15023(12) 0.01869(11) 0.0317(4) Uani 1 1 d . . . . .
Cl1 Cl 0.23771(13) 0.36157(3) -0.00357(3) 0.03625(12) Uani 1 1 d . . . . .
Cl2 Cl 0.44240(12) 0.48276(3) 0.16901(3) 0.03426(12) Uani 1 1 d . . . . .
N1 N -0.2225(4) 0.10156(10) -0.03756(9) 0.0319(3) Uani 1 1 d . . . . .
O1 O -0.3436(4) 0.04934(10) -0.09958(8) 0.0499(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
C1 0.0223(8) 0.0242(7) 0.0283(8) -0.0026(6) 0.0003(6) 0.0027(6)
C2 0.0211(8) 0.0252(7) 0.0261(7) 0.0030(6) 0.0021(6) 0.0045(6)
C3 0.0189(7) 0.0209(7) 0.0336(8) -0.0012(6) 0.0020(6) 0.0015(6)
C4 0.0271(9) 0.0293(7) 0.0276(7) -0.0049(6) 0.0006(7) 0.0019(7)
C5 0.0313(9) 0.0306(8) 0.0275(8) 0.0044(6) 0.0037(7) 0.0012(7)
C6 0.0273(8) 0.0233(7) 0.0338(8) 0.0015(6) 0.0033(8) -0.0011(7)
C7 0.0322(9) 0.0294(8) 0.0329(8) -0.0023(7) -0.0016(8) 0.0020(8)
Cl1 0.0416(2) 0.0380(2) 0.0296(2) 0.00801(16) 0.00574(19) -0.0003(2)
Cl2 0.0327(2) 0.02284(18) 0.0476(3) -0.00322(16) 0.0055(2) -0.00355(18)
N1 0.0380(8) 0.0280(6) 0.0285(7) -0.0006(6) -0.0061(6) 0.0044(7)
O1 0.0661(10) 0.0419(7) 0.0381(7) -0.0133(6) -0.0215(7) 0.0057(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
C1 C6 1.397(2) . ?
C1 C2 1.407(2) . ?
C1 C7 1.433(2) . ?
C2 C3 1.386(2) . ?
C2 Cl1 1.7212(16) . ?
C3 C4 1.386(2) . ?
C3 Cl2 1.7357(16) . ?
C4 C5 1.389(2) . ?
C4 H4 0.95 . ?
C5 C6 1.383(2) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.139(2) . ?
N1 O1 1.2347(18) . ?

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
C6 C1 C2 120.04(14) . . ?
C6 C1 C7 119.79(14) . . ?
C2 C1 C7 120.15(14) . . ?
C3 C2 C1 118.99(14) . . ?
C3 C2 Cl1 121.16(12) . . ?
C1 C2 Cl1 119.84(12) . . ?
C4 C3 C2 120.95(14) . . ?
C4 C3 Cl2 118.78(12) . . ?
C2 C3 Cl2 120.27(12) . . ?
C3 C4 C5 119.76(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.49(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.75(14) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C1 171.5(2) . . ?
C7 N1 O1 178.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

C7 C1 C2 C3 177.48(15) . . . . ?
C6 C1 C2 Cl1 179.02(12) . . . . ?
C7 C1 C2 Cl1 -2.3(2) . . . . ?
Cl1 C2 C3 C4 -179.98(13) . . . . ?
C1 C2 C3 Cl2 -179.36(12) . . . . ?
Cl1 C2 C3 Cl2 0.45(19) . . . . ?
Cl2 C3 C4 C5 -179.90(14) . . . . ?
C7 C1 C6 C5 -177.25(16) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046

_shelx_res_file                  
;

    15176a.res created by SHELXL-2014/7


TITL 15176a in P2(1)/c
CELL 0.71073 3.7857 12.6164 15.6315 90.000 93.847 90.000
ZERR 4.00 0.0010 0.0034 0.0041 0.000 0.004 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C  H  N  O  Cl
UNIT 28 12 4 4 8
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 5
LIST 4
SIZE 0.140 0.180 0.480
HTAB
CONF
TEMP -100
WGHT    0.025300    0.223800
BASF   0.38691
FVAR       0.94864
C1    1    0.004693    0.204341    0.096639    11.00000    0.02228    0.02422 =
         0.02832   -0.00262    0.00032    0.00265
C2    1    0.161863    0.305215    0.093792    11.00000    0.02110    0.02520 =
         0.02615    0.00300    0.00213    0.00455
C3    1    0.252090    0.357644    0.170090    11.00000    0.01886    0.02089 =
         0.03357   -0.00115    0.00197    0.00150
C4    1    0.190578    0.311933    0.248321    11.00000    0.02706    0.02926 =
         0.02765   -0.00491    0.00055    0.00190
AFIX  43
H4    2    0.251850    0.348945    0.300130    11.00000   -1.20000
AFIX   0
C5    1    0.039036    0.211821    0.250707    11.00000    0.03126    0.03057 =
         0.02753    0.00435    0.00366    0.00122
AFIX  43
H5    2   -0.002118    0.180350    0.304347    11.00000   -1.20000
AFIX   0
C6    1   -0.052426    0.157590    0.175551    11.00000    0.02727    0.02332 =
         0.03385    0.00150    0.00334   -0.00113
AFIX  43
H6    2   -0.153696    0.088816    0.177587    11.00000   -1.20000
AFIX   0
C7    1   -0.104279    0.150226    0.018689    11.00000    0.03219    0.02938 =
         0.03294   -0.00226   -0.00161    0.00196
CL1   5    0.237709    0.361569   -0.003566    11.00000    0.04165    0.03797 =
         0.02957    0.00801    0.00574   -0.00028
CL2   5    0.442403    0.482757    0.169010    11.00000    0.03274    0.02284 =
         0.04759   -0.00322    0.00553   -0.00355
N1    3   -0.222480    0.101561   -0.037563    11.00000    0.03797    0.02800 =
         0.02853   -0.00059   -0.00609    0.00444
O1    4   -0.343642    0.049341   -0.099580    11.00000    0.06614    0.04194 =
         0.03811   -0.01329   -0.02147    0.00574
HKLF 5

REM  15176a in P2(1)/c
REM R1 =  0.0254 for    1623 Fo > 4sig(Fo)  and  0.0277 for all    1712 data
REM    101 parameters refined using      0 restraints

END

WGHT      0.0253      0.2238

REM Instructions for potential hydrogen bonds
EQIV $1 x+1, -y+1/2, z+1/2
HTAB C4 O1_$1

REM Highest difference peak  0.264,  deepest hole -0.200,  1-sigma level  0.046
Q1    1   0.0560  0.2599  0.0933  11.00000  0.05    0.26
Q2    1   0.0511  0.1805  0.1379  11.00000  0.05    0.24
Q3    1   0.1085  0.2614  0.2479  11.00000  0.05    0.21
Q4    1   0.1483  0.3438  0.2069  11.00000  0.05    0.20
Q5    1  -0.0498  0.2000  0.2121  11.00000  0.05    0.20
;
_shelx_res_checksum              78697

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_14141z4Cl
_database_code_depnum_ccdc_archive 'CCDC 1879705'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2018-12-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-chlorobenzonitrile-N-oxide
_chemical_name_common            '4-chlorobenzonitrile oxide'
_chemical_melting_point          '353-356 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.50 H2 Cl0.50 N0.50 O0.50'
_chemical_formula_weight         76.78

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'
O O 0.0106 0.0060 '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           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   4.5995(4)
_cell_length_b                   7.7964(7)
_cell_length_c                   9.3711(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.2010(10)
_cell_angle_gamma                90
_cell_volume                     329.64(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    643
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      27.22

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   0.6579
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.493
_shelx_estimated_absorpt_T_min   0.6579
_shelx_estimated_absorpt_T_max   0.7455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6579
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS 2012/1 (Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2880
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         27.343
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             792
_reflns_number_gt                740
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) Mercury (Allen et al, 2004)'
_computing_publication_material  'Bruker 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)+(0.0341P)²+0.0940P] 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         792
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0675
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.6088(3) 0.2500 0.15782(17) 0.0271(4) Uani 1 2 d S T P . .
C2 C 0.5286(3) 0.40510(17) 0.21278(12) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.5832 0.5105 0.1744 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3689(2) 0.40509(16) 0.32364(12) 0.0278(3) Uani 1 1 d . . . . .
H3 H 0.3109 0.5101 0.3613 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2949(3) 0.2500 0.37870(17) 0.0243(3) Uani 1 2 d S T P . .
C7 C 0.7787(4) 0.2500 0.04467(19) 0.0330(4) Uani 1 2 d S T P . .
Cl1 Cl 0.11380(9) 0.2500 0.52480(5) 0.03269(16) Uani 1 2 d S T P . .
N1 N 0.9123(3) 0.2500 -0.04572(15) 0.0300(3) Uani 1 2 d S T P . .
O1 O 1.0566(3) 0.2500 -0.14367(15) 0.0429(4) 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 0.0218(8) 0.0355(9) 0.0239(8) 0.000 0.0040(6) 0.000
C2 0.0290(6) 0.0288(6) 0.0296(6) 0.0040(5) 0.0063(5) -0.0021(5)
C3 0.0285(6) 0.0254(6) 0.0300(6) -0.0005(5) 0.0067(5) 0.0020(5)
C4 0.0201(7) 0.0298(9) 0.0232(7) 0.000 0.0047(6) 0.000
C7 0.0296(9) 0.0408(11) 0.0288(9) 0.000 0.0064(7) 0.000
Cl1 0.0329(3) 0.0363(3) 0.0327(2) 0.000 0.01577(17) 0.000
N1 0.0298(7) 0.0323(8) 0.0294(7) 0.000 0.0099(6) 0.000
O1 0.0477(8) 0.0502(9) 0.0379(7) 0.000 0.0258(6) 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 C2 1.3919(15) . ?
C1 C7 1.434(2) . ?
C2 C3 1.3840(16) . ?
C2 H2 0.95 . ?
C3 C4 1.3828(14) . ?
C3 H3 0.95 . ?
C4 Cl1 1.7354(16) . ?
C7 N1 1.139(2) . ?
N1 O1 1.2327(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C2 120.62(15) . 4_565 ?
C2 C1 C7 119.69(7) . . ?
C3 C2 C1 119.68(11) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.01(11) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C3 121.95(15) 4_565 . ?
C3 C4 Cl1 119.01(7) . . ?
N1 C7 C1 179.65(18) . . ?
C7 N1 O1 179.92(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag

C7 C1 C2 C3 -178.93(13) . . . . ?
C2 C3 C4 Cl1 176.25(9) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.039

_shelx_res_file                  
;

    14141z.res created by SHELXL-2014/7


TITL 14141a in P2(1)/m
CELL 0.71073 4.5995 7.7964 9.3711 90.000 101.201 90.000
ZERR 4.00    0.0004 0.0007 0.0008  0.000   0.001  0.000
LATT 1
SYMM -x, y+1/2, -z
SFAC C  H  N  O  Cl
UNIT 14 8 2 2 2
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 8
ACTA
BOND $H
FMAP 2
PLAN 0
CONF
HTAB
MPLA 4 C1 C2 C3 C4 Cl1 C7 N1 O1
TEMP -100
WGHT    0.034100    0.094000
FVAR       0.41740
C1    1    0.608820    0.250000    0.157824    10.50000    0.02180    0.03551 =
         0.02389    0.00000    0.00397    0.00000
C2    1    0.528591    0.405099    0.212780    11.00000    0.02905    0.02880 =
         0.02959    0.00405    0.00634   -0.00207
AFIX  43
H2    2    0.583206    0.510459    0.174375    11.00000   -1.20000
AFIX   0
C3    1    0.368876    0.405091    0.323638    11.00000    0.02847    0.02539 =
         0.02998   -0.00051    0.00671    0.00197
AFIX  43
H3    2    0.310897    0.510075    0.361343    11.00000   -1.20000
AFIX   0
C4    1    0.294942    0.250000    0.378705    10.50000    0.02008    0.02981 =
         0.02318    0.00000    0.00468    0.00000
C7    1    0.778729    0.250000    0.044665    10.50000    0.02959    0.04083 =
         0.02882    0.00000    0.00642    0.00000
CL1   5    0.113798    0.250000    0.524795    10.50000    0.03291    0.03630 =
         0.03267    0.00000    0.01577    0.00000
N1    3    0.912326    0.250000   -0.045718    10.50000    0.02982    0.03229 =
         0.02941    0.00000    0.00985    0.00000
O1    4    1.056608    0.250000   -0.143667    10.50000    0.04773    0.05024 =
         0.03788    0.00000    0.02576    0.00000
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  14141a in P2(1)/m
REM R1 =  0.0244 for     740 Fo > 4sig(Fo)  and  0.0269 for all     792 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0336      0.0975

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.277,  deepest hole -0.159,  1-sigma level  0.039
Q1    1   0.3533  0.3297  0.3575  11.00000  0.05    0.28
Q2    1   0.4850  0.3949  0.2822  11.00000  0.05    0.28
Q3    1   0.6077  0.1751  0.1935  11.00000  0.05    0.25
Q4    1   0.3796  0.3992  0.2418  11.00000  0.05    0.24
Q5    1   0.1925  0.2500  0.4386  10.50000  0.05    0.22
Q6    1   0.7129  0.2500  0.1211  10.50000  0.05    0.19
Q7    1   0.9157  0.1958  0.0193  11.00000  0.05    0.13
Q8    1   0.7855  0.2003 -0.0344  11.00000  0.05    0.12
Q9    1   0.5469  0.4386  0.1970  11.00000  0.05    0.12
Q10   1   0.3182  0.2500  0.5328  10.50000  0.05    0.11
Q11   1   0.3537  0.4372  0.3464  11.00000  0.05    0.11
Q12   1  -0.1247  0.2500  0.5179  10.50000  0.05    0.10
Q13   1   0.2015  0.2500  0.3432  10.50000  0.05    0.09
Q14   1   0.9337  0.2500 -0.2108  10.50000  0.05    0.09
Q15   1   0.8985  0.2500 -0.1661  10.50000  0.05    0.08
Q16   1   1.0514  0.2500 -0.0844  10.50000  0.05    0.08
Q17   1   0.8708  0.5235  0.0580  11.00000  0.05    0.08
Q18   1   0.0344  0.2500  0.2559  10.50000  0.05    0.07
Q19   1   0.6807  0.5343  0.2302  11.00000  0.05    0.07
Q20   1   1.0476  0.1682 -0.1159  11.00000  0.05    0.07
;
_shelx_res_checksum              28104

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
