# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_Nagib2149
_database_code_depnum_ccdc_archive 'CCDC 1581032'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;

_audit_creation_date             2017-10-18T11:59:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C8 H12 Br2 Cl3 N O'
_chemical_formula_sum            'C8 H12 Br2 Cl3 N O'
_chemical_formula_weight         404.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   18.3209(5)
_cell_length_b                   12.3996(3)
_cell_length_c                   12.1068(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.7660(10)
_cell_angle_gamma                90
_cell_volume                     2718.20(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9102
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      27.89
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.976
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_special_details           
;All work was done at 150 K using an Oxford Cryosystems 
 Cryostream Cooler.  

Phi and omega scans with a frame width of 0.5 degree were
used for data collection. 
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_T_max  0.647
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS )'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_source                   'fine--focus tube'
_diffrn_measurement_device       'Bruker D8 Venture PHOTON II CPAD'
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_number            36801
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.286
_diffrn_reflns_theta_max         27.887
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             3252
_reflns_number_gt                2953
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT v8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT_2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;For the methyl groups, the hydrogen atoms were added at 
 calculated positions using a riding model with 
 U(H) = 1.5 * Ueq(bonded carbon atom). The torsion angle, which defines 
 the orientation of the methyl group about the C-C bond, 
 was refined. 
 
 The hydrogen atom bonded to the nitrogen atom is disordered over
 two sites.  Both sites were assigned an occupancy factor of 0.5 and
 their coordinates were fixed at their positions as located in a difference
 electron density map.  The Uiso values were refined. 

 The remaining hydrogen atoms were added at calculated positions 
 using a riding model with U(H) = 1.2 * Ueq(bonded carbon atom).,The hydrogen atom bonded to nitrogen is disordered over two sites.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0139P)²+4.3311P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3252
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0404
_refine_ls_wR_factor_gt          0.0392
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51420(9) 0.74453(14) 0.48268(15) 0.0227(3) Uani 1 d . .
C2 C 0.45195(9) 0.68312(14) 0.52808(14) 0.0220(3) Uani 1 d . .
C3 C 0.33806(9) 0.59868(14) 0.47369(13) 0.0199(3) Uani 1 d . .
H3A H 0.3109 0.6422 0.5227 0.024 Uiso 1 calc . .
H3B H 0.3571 0.5332 0.5152 0.024 Uiso 1 calc . .
C4 C 0.28660(9) 0.56705(13) 0.36851(13) 0.0164(3) Uani 1 d . .
C5 C 0.21868(9) 0.50104(13) 0.39265(14) 0.0184(3) Uani 1 d . .
C6 C 0.16872(10) 0.46923(15) 0.28446(15) 0.0246(4) Uani 1 d . .
H6A H 0.1968 0.4253 0.2383 0.037 Uiso 1 calc . .
H6B H 0.1508 0.5344 0.2433 0.037 Uiso 1 calc . .
H6C H 0.1266 0.4276 0.3025 0.037 Uiso 1 calc . .
C7 C 0.17245(10) 0.56787(17) 0.46368(17) 0.0313(4) Uani 1 d . .
H7A H 0.156 0.6345 0.4239 0.047 Uiso 1 calc . .
H7B H 0.2026 0.5858 0.5353 0.047 Uiso 1 calc . .
H7C H 0.1293 0.5259 0.4771 0.047 Uiso 1 calc . .
C8 C 0.24501(10) 0.39820(15) 0.45794(15) 0.0253(4) Uani 1 d . .
H8A H 0.2024 0.3522 0.4646 0.038 Uiso 1 calc . .
H8B H 0.2699 0.4179 0.5327 0.038 Uiso 1 calc . .
H8C H 0.2795 0.359 0.4181 0.038 Uiso 1 calc . .
N N 0.45022(10) 0.65784(18) 0.62523(14) 0.0441(5) Uani 1 d . .
H1N H 0.491 0.6639 0.6627 0.023(10) Uiso 0.5 d . .
H2N H 0.4188 0.6467 0.6434 0.019(12) Uiso 0.5 d . .
O O 0.39867(6) 0.66040(10) 0.44351(10) 0.0236(3) Uani 1 d . .
Cl1 Cl 0.47789(2) 0.85749(4) 0.40366(4) 0.03068(10) Uani 1 d . .
Cl2 Cl 0.58064(3) 0.78879(4) 0.59455(4) 0.03602(12) Uani 1 d . .
Cl3 Cl 0.55679(3) 0.65778(4) 0.39551(4) 0.03543(11) Uani 1 d . .
Br1 Br 0.34532(2) 0.48508(2) 0.27370(2) 0.02317(5) Uani 1 d . .
Br2 Br 0.25488(2) 0.70054(2) 0.28696(2) 0.02740(5) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.541(2) . ?
C1 Cl2 1.7649(17) . ?
C1 Cl1 1.7680(18) . ?
C1 Cl3 1.7694(18) . ?
C2 N 1.222(2) . ?
C2 O 1.3327(19) . ?
C3 O 1.4408(19) . ?
C3 C4 1.516(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 C5 1.554(2) . ?
C4 Br2 1.9691(16) . ?
C4 Br1 1.9707(16) . ?
C5 C6 1.531(2) . ?
C5 C7 1.538(2) . ?
C5 C8 1.539(2) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
N H1N 0.816 . ?
N H2N 0.662 . ?

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 Cl2 109.96(12) . . ?
C2 C1 Cl1 110.28(12) . . ?
Cl2 C1 Cl1 109.12(10) . . ?
C2 C1 Cl3 109.27(12) . . ?
Cl2 C1 Cl3 109.36(9) . . ?
Cl1 C1 Cl3 108.83(10) . . ?
N C2 O 124.17(16) . . ?
N C2 C1 126.81(16) . . ?
O C2 C1 109.01(14) . . ?
O C3 C4 109.21(13) . . ?
O C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C3 C4 C5 113.05(13) . . ?
C3 C4 Br2 107.58(11) . . ?
C5 C4 Br2 110.70(10) . . ?
C3 C4 Br1 107.33(11) . . ?
C5 C4 Br1 111.21(10) . . ?
Br2 C4 Br1 106.69(7) . . ?
C6 C5 C7 107.99(14) . . ?
C6 C5 C8 109.01(14) . . ?
C7 C5 C8 108.40(15) . . ?
C6 C5 C4 111.48(14) . . ?
C7 C5 C4 110.27(13) . . ?
C8 C5 C4 109.62(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 N H1N 110.8 . . ?
C2 N H2N 121.7 . . ?
H1N N H2N 127.1 . . ?
C2 O C3 114.84(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl2 C1 C2 N -6.8(3) . . . . ?
Cl1 C1 C2 N -127.1(2) . . . . ?
Cl3 C1 C2 N 113.3(2) . . . . ?
Cl2 C1 C2 O 173.49(12) . . . . ?
Cl1 C1 C2 O 53.11(17) . . . . ?
Cl3 C1 C2 O -66.48(16) . . . . ?
O C3 C4 C5 -179.32(13) . . . . ?
O C3 C4 Br2 -56.79(15) . . . . ?
O C3 C4 Br1 57.69(15) . . . . ?
C3 C4 C5 C6 -179.15(14) . . . . ?
Br2 C4 C5 C6 60.08(15) . . . . ?
Br1 C4 C5 C6 -58.33(15) . . . . ?
C3 C4 C5 C7 60.91(18) . . . . ?
Br2 C4 C5 C7 -59.86(16) . . . . ?
Br1 C4 C5 C7 -178.27(12) . . . . ?
C3 C4 C5 C8 -58.36(18) . . . . ?
Br2 C4 C5 C8 -179.12(11) . . . . ?
Br1 C4 C5 C8 62.46(15) . . . . ?
N C2 O C3 -2.3(3) . . . . ?
C1 C2 O C3 177.49(14) . . . . ?
C4 C3 O C2 -173.10(14) . . . . ?

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
C3 H3B Cl3 0.99 2.96 3.9244(18) 165.8 5_666
N H1N N 0.816 2.629 3.282(3) 138.1 2_656
N H1N Cl2 0.816 2.488 2.9587(18) 117.9 .
N H2N Br1 0.662 2.760 3.3345(18) 147.0 6_566


# END of CIF
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
