# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1941460'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-08-21 downloaded from the CCDC.
;


_audit_creation_method           'MoPro v16                '
_chemical_name_systematic        N-n-butyltetrachlorophthalimide
_chemical_name_common            ?
_chemical_formula_moiety         'C12 H9 Cl4 N O2'
_chemical_formula_sum            'C12 H9 Cl4 N O2'
_chemical_formula_weight         341.004
_chemical_absolute_configuration .

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
Cl Cl 0.1484 0.1585
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a                   5.19987(6)
_cell_length_b                   11.27107(12)
_cell_length_c                   12.08308(11)
_cell_angle_alpha                103.6423(8)
_cell_angle_beta                 98.8523(9)
_cell_angle_gamma                101.4977(9)
_cell_volume                     659.199(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    47140
_cell_measurement_theta_min      3.5270
_cell_measurement_theta_max      57.5870
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.318
_exptl_crystal_size_min          0.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
;
_diffrn_ambient_temperature      100(1)
_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  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            110748
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0223
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         57.70
_reflns_number_total             16010
_reflns_number_gt                16002
_reflns_threshold_expression     >2.0sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'

_refine_special_details          
;
 Refinement of F¹ against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) 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 F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     'Isotropic Gaussian'
_refine_ls_extinction_coef       0.07166
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         16010
_refine_ls_number_parameters     627
_refine_ls_number_restraints     336
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0131
## R_factor_all computed for  I/sigmaI >   2.00
_refine_ls_R_factor_gt           0.0131
_refine_ls_wR_factor_ref         0.0160
_refine_ls_wR_factor_gt          0.0160
_refine_ls_goodness_of_fit_ref   0.926
# GOF(F) computed assuming  all parameters refined:     765
_refine_ls_restrained_S_all      0.627
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        57.70
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl CL7 0.732712(8) 0.495776(4) 0.371973(4) 0.013124(6) Uani 1 d . . . .
Cl CL4 0.015820(8) 0.882387(4) 0.376639(4) 0.013876(6) Uani 1 d . . . .
Cl CL5 -0.050400(10) 0.663766(5) 0.153141(4) 0.017910(8) Uani 1 d . . . .
Cl CL6 0.297023(11) 0.470596(5) 0.149925(4) 0.019928(9) Uani 1 d . . . .
O O9 0.90392(4) 0.680677(18) 0.624414(16) 0.01625(2) Uani 1 d . . . .
O O2 0.35901(4) 0.953226(18) 0.633478(17) 0.01698(3) Uani 1 d . . . .
N N1 0.65611(3) 0.829528(15) 0.657343(13) 0.01264(2) Uani 1 d . . . .
C C6 0.34343(3) 0.591217(16) 0.273018(13) 0.01278(2) Uani 1 d . . . .
C C3 0.39467(3) 0.782019(14) 0.473383(13) 0.010935(19) Uani 1 d . . . .
C C5 0.18585(3) 0.679065(16) 0.274126(14) 0.01258(2) Uani 1 d . . . .
C C8 0.55486(3) 0.696398(14) 0.471634(13) 0.01077(2) Uani 1 d . . . .
C C4 0.21158(3) 0.776844(15) 0.375311(13) 0.01152(2) Uani 1 d . . . .
C C9 0.73043(3) 0.728790(15) 0.590145(13) 0.01156(2) Uani 1 d . . . .
C C7 0.53438(3) 0.600364(14) 0.372765(13) 0.01137(2) Uani 1 d . . . .
C C2 0.45689(3) 0.867862(15) 0.594222(14) 0.01207(2) Uani 1 d . . . .
C C10 0.75962(4) 0.881568(19) 0.782340(15) 0.01432(2) Uani 1 d . . . .
H H10A 0.8128(13) 0.98408(18) 0.8019(5) 0.0337(17) Uani 1 d D . . .
H H10B 0.9446(7) 0.8521(6) 0.8032(5) 0.035(2) Uani 1 d D . . .
C C11 0.55742(4) 0.836078(17) 0.851883(14) 0.01423(2) Uani 1 d . . . .
H H11A 0.3880(8) 0.8786(5) 0.8388(5) 0.0352(17) Uani 1 d D . . .
H H11B 0.4806(13) 0.73420(19) 0.8181(5) 0.0364(18) Uani 1 d D . . .
C C12 0.67995(4) 0.86793(2) 0.981476(16) 0.01607(3) Uani 1 d . . . .
H H12A 0.7507(13) 0.96995(19) 1.0167(5) 0.0370(19) Uani 1 d D . . .
H H12B 0.8558(8) 0.8292(6) 0.9916(6) 0.040(2) Uani 1 d D . . .
C C13 0.48216(5) 0.81679(3) 1.04992(2) 0.02144(4) Uani 1 d . . . .
H H13A 0.4153(15) 0.71572(18) 1.0191(6) 0.046(2) Uani 1 d D . . .
H H13B 0.3034(8) 0.8508(6) 1.0377(7) 0.048(2) Uani 1 d D . . .
H H13C 0.5661(14) 0.8416(7) 1.1419(2) 0.046(2) Uani 1 d D . . .


_geom_special_details            
;                                    
;

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
CL7 C7 1.71337(15) . ?
CL4 C4 1.71184(15) . ?
CL5 C5 1.70877(16) . ?
CL6 C6 1.70987(17) . ?
O9 C9 1.2105(2) . ?
O2 C2 1.2100(2) . ?
N1 C2 1.3901(2) . ?
N1 C9 1.3908(2) . ?
N1 C10 1.4564(2) . ?
C6 C5 1.4045(2) . ?
C6 C7 1.4077(2) . ?
C3 C4 1.3828(2) . ?
C3 C2 1.4954(2) . ?
C3 C8 1.3935(2) . ?
C5 C4 1.4080(2) . ?
C8 C7 1.3838(2) . ?
C8 C9 1.4952(2) . ?
C10 C11 1.5280(3) . ?
C10 H10A 1.0913(18) . ?
C10 H10B 1.0914(18) . ?
C11 C12 1.5243(2) . ?
C11 H11B 1.0911(18) . ?
C11 H11A 1.0922(18) . ?
C12 C13 1.5246(3) . ?
C12 H12A 1.0913(18) . ?
C12 H12B 1.0918(18) . ?
C13 H13A 1.0767(18) . ?
C13 H13B 1.0768(19) . ?
C13 H13C 1.0769(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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 112.664(12) . . . ?
C2 N1 C10 123.786(13) . . . ?
C9 N1 C10 123.348(13) . . . ?
CL6 C6 C5 119.380(11) . . . ?
CL6 C6 C7 120.007(11) . . . ?
C5 C6 C7 120.600(12) . . . ?
C4 C3 C2 130.538(12) . . . ?
C4 C3 C8 121.484(12) . . . ?
C2 C3 C8 107.956(11) . . . ?
CL5 C5 C6 119.746(10) . . . ?
CL5 C5 C4 119.270(11) . . . ?
C6 C5 C4 120.929(13) . . . ?
C7 C8 C9 130.314(12) . . . ?
C7 C8 C3 121.787(12) . . . ?
C9 C8 C3 107.890(11) . . . ?
CL4 C4 C5 120.692(10) . . . ?
CL4 C4 C3 121.706(10) . . . ?
C5 C4 C3 117.581(13) . . . ?
O9 C9 N1 125.146(14) . . . ?
O9 C9 C8 129.127(13) . . . ?
N1 C9 C8 105.727(12) . . . ?
CL7 C7 C6 121.178(10) . . . ?
CL7 C7 C8 121.246(10) . . . ?
C6 C7 C8 117.575(12) . . . ?
O2 C2 N1 124.984(14) . . . ?
O2 C2 C3 129.303(14) . . . ?
N1 C2 C3 105.710(12) . . . ?
N1 C10 C11 111.668(13) . . . ?
N1 C10 H10A 108.3(3) . . . ?
N1 C10 H10B 107.1(3) . . . ?
C11 C10 H10A 111.5(3) . . . ?
C11 C10 H10B 110.6(3) . . . ?
H10A C10 H10B 107.5(5) . . . ?
C10 C11 C12 112.501(14) . . . ?
C10 C11 H11B 109.2(3) . . . ?
C10 C11 H11A 108.6(3) . . . ?
C12 C11 H11B 108.8(3) . . . ?
C12 C11 H11A 110.0(3) . . . ?
H11B C11 H11A 107.6(5) . . . ?
C11 C12 C13 112.496(15) . . . ?
C11 C12 H12A 109.3(3) . . . ?
C11 C12 H12B 108.5(3) . . . ?
C13 C12 H12A 109.6(3) . . . ?
C13 C12 H12B 109.9(3) . . . ?
H12A C12 H12B 107.0(5) . . . ?
C12 C13 H13A 111.1(4) . . . ?
C12 C13 H13B 110.9(4) . . . ?
C12 C13 H13C 112.7(4) . . . ?
H13A C13 H13B 105.5(6) . . . ?
H13A C13 H13C 108.0(6) . . . ?
H13B C13 H13C 108.4(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
CL7 C7 C6 CL6 . . . . 2.554(13) ?
CL7 C7 C6 C5 . . . . -178.725(3) ?
CL7 C7 C8 C9 . . . . -1.197(15) ?
CL7 C7 C8 C3 . . . . -179.9720(9) ?
CL4 C4 C5 CL5 . . . . -1.851(13) ?
CL4 C4 C5 C6 . . . . -179.1448(16) ?
CL4 C4 C3 C2 . . . . 2.391(15) ?
CL4 C4 C3 C8 . . . . -179.5590(8) ?
CL5 C5 C6 CL6 . . . . 0.339(14) ?
CL5 C5 C6 C7 . . . . -178.391(3) ?
CL5 C5 C4 C3 . . . . 176.520(6) ?
CL6 C6 C5 C4 . . . . 177.620(5) ?
CL6 C6 C7 C8 . . . . -177.056(6) ?
O9 C9 N1 C2 . . . . 178.07(2) ?
O9 C9 N1 C10 . . . . -6.93(2) ?
O9 C9 C8 C7 . . . . 3.71(2) ?
O9 C9 C8 C3 . . . . -177.37(3) ?
O2 C2 N1 C9 . . . . 179.84(2) ?
O2 C2 N1 C10 . . . . 4.87(2) ?
O2 C2 C3 C4 . . . . -0.02(2) ?
O2 C2 C3 C8 . . . . -178.26(3) ?
N1 C2 C3 C4 . . . . 179.40(2) ?
N1 C2 C3 C8 . . . . 1.15(2) ?
N1 C9 C8 C7 . . . . -176.56(2) ?
N1 C9 C8 C3 . . . . 2.35(2) ?
N1 C10 C11 C12 . . . . 168.78(14) ?
N1 C10 C11 H11B . . . . 47.9(7) ?
N1 C10 C11 H11A . . . . -69.2(6) ?
C6 C5 C4 C3 . . . . -0.77(2) ?
C6 C7 C8 C9 . . . . 178.41(2) ?
C6 C7 C8 C3 . . . . -0.37(2) ?
C3 C2 N1 C9 . . . . 0.40(2) ?
C3 C2 N1 C10 . . . . -174.58(2) ?
C5 C6 C7 C8 . . . . 1.67(2) ?
C5 C4 C3 C2 . . . . -175.96(2) ?
C5 C4 C3 C8 . . . . 2.09(2) ?
C8 C9 N1 C2 . . . . -1.67(2) ?
C8 C9 N1 C10 . . . . 173.33(2) ?
C4 C5 C6 C7 . . . . -1.11(2) ?
C4 C3 C8 C7 . . . . -1.55(2) ?
C4 C3 C8 C9 . . . . 179.42(2) ?
C9 N1 C10 C11 . . . . -101.47(3) ?
C9 N1 C10 H10A . . . . 135.3(7) ?
C9 N1 C10 H10B . . . . 19.8(7) ?
C9 C8 C3 C2 . . . . -2.14(2) ?
C7 C8 C3 C2 . . . . 176.89(2) ?
C2 N1 C10 C11 . . . . 72.98(3) ?
C2 N1 C10 H10A . . . . -50.2(7) ?
C2 N1 C10 H10B . . . . -165.8(8) ?
C10 C11 C12 C13 . . . . -177.12(3) ?
C10 C11 C12 H12A . . . . 60.9(7) ?
C10 C11 C12 H12B . . . . -55.3(7) ?
H10A C10 C11 C12 . . . . -69.9(6) ?
H10A C10 C11 H11B . . . . 169.(2) ?
H10A C10 C11 H11A . . . . 52.2(10) ?
H10B C10 C11 C12 . . . . 49.6(7) ?
H10B C10 C11 H11B . . . . -71.3(10) ?
H10B C10 C11 H11A . . . . 171.7(9) ?
C11 C12 C13 H13A . . . . 60.5(8) ?
C11 C12 C13 H13B . . . . -56.5(8) ?
C11 C12 C13 H13C . . . . -178.17(9) ?
H11A C11 C12 C13 . . . . 61.6(6) ?
H11A C11 C12 H12A . . . . -60.3(10) ?
H11A C11 C12 H12B . . . . -176.6(9) ?
H11B C11 C12 C13 . . . . -56.0(7) ?
H11B C11 C12 H12A . . . . -178.(1) ?
H11B C11 C12 H12B . . . . 65.8(10) ?
H12A C12 C13 H13A . . . . -177.7(10) ?
H12A C12 C13 H13B . . . . 65.(1) ?
H12A C12 C13 H13C . . . . -56.(1) ?
H12B C12 C13 H13A . . . . -60.(1) ?
H12B C12 C13 H13B . . . . -177.5(10) ?
H12B C12 C13 H13C . . . . 61.(1) ?

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
### Notice sigmas on distances involving HYDROGEN atoms 
### is generally not recommended.
### this may cause reading errors in checkcif
C10 H10B O9 1.0914(18) 2.485(6) 2.9002(2) 101.1(3) 1



#
# h,k,l, Fc-squared, Fo-squared, sigma(Fo-squared), status flag
#

_reflns_d_resolution_high        0.4204

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
