# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_d1
_database_code_depnum_ccdc_archive 'CCDC 1587327'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl0.04 N2 O2'
_chemical_formula_weight         215.70

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'-y+2/3, -x+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
'-y+1/3, -x+2/3, z+7/6'

_cell_length_a                   19.7298(7)
_cell_length_b                   19.7298(7)
_cell_length_c                   19.0360(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6417.3(4)
_cell_formula_units_Z            24
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2705
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22297
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         27.93
_reflns_number_total             3388
_reflns_number_gt                2805
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0482P)²+7.7514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_number_reflns         3388
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.77527(5) 0.27124(5) 0.01283(4) 0.0533(2) Uani 1 1 d . . .
O002 O 0.57180(10) 0.21815(10) 0.17964(9) 0.0283(4) Uani 1 1 d . . .
N003 N 0.65792(10) 0.07282(10) 0.13514(10) 0.0181(4) Uani 1 1 d . . .
N004 N 0.53753(10) -0.03731(11) 0.14559(10) 0.0179(4) Uani 1 1 d . . .
N005 N 0.67142(11) 0.19797(11) 0.14761(10) 0.0213(4) Uani 1 1 d . . .
H005 H 0.7031 0.2476 0.1446 0.026 Uiso 1 1 calc R . .
C006 C 0.59479(13) 0.17207(13) 0.16548(11) 0.0190(5) Uani 1 1 d . . .
C007 C 0.82580(13) 0.15441(15) 0.15529(13) 0.0261(5) Uani 1 1 d . . .
H007 H 0.8001 0.1173 0.1902 0.031 Uiso 1 1 calc R . .
C008 C 0.54459(13) 0.08724(13) 0.16543(11) 0.0164(4) Uani 1 1 d . . .
C009 C 0.78495(13) 0.18278(14) 0.11824(12) 0.0224(5) Uani 1 1 d . . .
C010 C 0.45883(13) -0.07245(12) 0.15723(11) 0.0170(5) Uani 1 1 d . . .
C011 C 0.41402(14) -0.15472(14) 0.15031(13) 0.0248(5) Uani 1 1 d . . .
H011 H 0.4386 -0.1832 0.1397 0.030 Uiso 1 1 calc R . .
C012 C 0.29656(15) -0.15066(16) 0.17620(13) 0.0282(6) Uani 1 1 d . . .
H012 H 0.2425 -0.1774 0.1816 0.034 Uiso 1 1 calc R . .
C013 C 0.90271(18) 0.26268(16) 0.05086(15) 0.0421(8) Uani 1 1 d . . .
H013 H 0.9286 0.2989 0.0153 0.050 Uiso 1 1 calc R . .
C014 C 0.42059(13) -0.02963(14) 0.17515(11) 0.0194(5) Uani 1 1 d . . .
C015 C 0.46578(13) 0.05151(14) 0.17987(12) 0.0190(5) Uani 1 1 d . . .
H015 H 0.4430 0.0812 0.1926 0.023 Uiso 1 1 calc R . .
C016 C 0.82361(16) 0.23725(14) 0.06515(14) 0.0335(6) Uani 1 1 d . . .
C017 C 0.33752(13) -0.07194(15) 0.18487(13) 0.0244(5) Uani 1 1 d . . .
H017 H 0.3115 -0.0453 0.1972 0.029 Uiso 1 1 calc R . .
C018 C 0.33479(15) -0.19238(14) 0.15922(13) 0.0287(6) Uani 1 1 d . . .
H018 H 0.3057 -0.2464 0.1540 0.034 Uiso 1 1 calc R . .
C019 C 0.69960(13) 0.14853(13) 0.13446(12) 0.0185(5) Uani 1 1 d . . .
C020 C 0.90386(15) 0.17955(19) 0.14194(15) 0.0385(7) Uani 1 1 d . . .
H020 H 0.9303 0.1600 0.1679 0.046 Uiso 1 1 calc R . .
C021 C 0.57840(12) 0.03978(12) 0.14930(11) 0.0147(4) Uani 1 1 d . . .
C022 C 0.94193(16) 0.23403(18) 0.08945(16) 0.0421(8) Uani 1 1 d . . .
H022 H 0.9944 0.2514 0.0801 0.051 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cl01 C016 1.729(3) . ?
O002 C006 1.232(3) . ?
N003 C019 1.296(3) . ?
N003 C021 1.391(3) . ?
N004 C021 1.320(3) . ?
N004 C010 1.365(3) . ?
N005 C019 1.366(3) . ?
N005 C006 1.375(3) . ?
C006 C008 1.458(3) . ?
C007 C009 1.383(4) . ?
C007 C020 1.385(3) . ?
C008 C015 1.376(3) . ?
C008 C021 1.429(3) . ?
C009 C016 1.392(3) . ?
C009 C019 1.500(3) . ?
C010 C011 1.414(3) . ?
C010 C014 1.427(3) . ?
C011 C018 1.365(4) . ?
C012 C017 1.355(4) . ?
C012 C018 1.404(4) . ?
C013 C022 1.377(5) . ?
C013 C016 1.406(4) . ?
C014 C015 1.392(3) . ?
C014 C017 1.432(3) . ?
C020 C022 1.382(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
C019 N003 C021 117.3(2) . . ?
C021 N004 C010 117.45(19) . . ?
C019 N005 C006 122.99(19) . . ?
O002 C006 N005 121.5(2) . . ?
O002 C006 C008 123.9(2) . . ?
N005 C006 C008 114.60(19) . . ?
C009 C007 C020 122.0(3) . . ?
C015 C008 C021 119.0(2) . . ?
C015 C008 C006 122.2(2) . . ?
C021 C008 C006 118.75(19) . . ?
C007 C009 C016 118.5(2) . . ?
C007 C009 C019 117.6(2) . . ?
C016 C009 C019 123.8(2) . . ?
N004 C010 C011 117.9(2) . . ?
N004 C010 C014 122.81(19) . . ?
C011 C010 C014 119.3(2) . . ?
C018 C011 C010 120.1(2) . . ?
C017 C012 C018 120.8(2) . . ?
C022 C013 C016 120.1(3) . . ?
C015 C014 C010 118.2(2) . . ?
C015 C014 C017 123.4(2) . . ?
C010 C014 C017 118.4(2) . . ?
C008 C015 C014 119.1(2) . . ?
C009 C016 C013 119.9(3) . . ?
C009 C016 Cl01 121.5(2) . . ?
C013 C016 Cl01 118.6(2) . . ?
C012 C017 C014 120.3(2) . . ?
C011 C018 C012 120.9(2) . . ?
N003 C019 N005 124.8(2) . . ?
N003 C019 C009 116.4(2) . . ?
N005 C019 C009 118.8(2) . . ?
C022 C020 C007 119.1(3) . . ?
N004 C021 N003 115.19(18) . . ?
N004 C021 C008 123.4(2) . . ?
N003 C021 C008 121.41(19) . . ?
C013 C022 C020 120.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.052
