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

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

data_briso4clnh2cl_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1528385'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

_audit_creation_date             2016-10-05T14:45:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
4-Carbomethoxy-7-(4-chlorophenylamino)-6-bromo-3-bromoethyl-1-methyl-5,8-dioxo-5,8-dihydroisoquinoline
_chemical_formula_moiety         'C19 H13 Br2 Cl N2 O4'
_chemical_formula_sum            'C19 H13 Br2 Cl N2 O4'
_chemical_formula_weight         528.58

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_Int_Tables_number      18
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   20.5261(10)
_cell_length_b                   9.0318(5)
_cell_length_c                   10.5375(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1953.52(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3754
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      24.46


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

_exptl_crystal_colour            ' dark red'
_exptl_crystal_description       ' plate'
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.016
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_F_000             1040
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    4.315
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) 
was 0.0795 before and 0.0397 after correction. The Ratio of minimum 
to maximum transmission is 0.8335. The λ/2 correction factor is 0.00150.
;

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

_diffrn_measurement_device       'Bruker D8 Venture diffractometer'
_diffrn_detector                 'Photon 100 detector'
_diffrn_detector_type            'CMOS area detector'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar multilayer mirror'
_diffrn_source                   'Microfocus sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_number            5449
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_reflns_number_total             3687
_reflns_number_gt                2444
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_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)+(0.0246P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3687
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.052
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1117
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.009(16)
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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'
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'

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
Br1 Br 0.48489(5) 0.72710(13) 0.05243(10) 0.0628(3) Uani 1 d . .
Br2 Br 0.31683(7) 0.69738(13) 0.80801(13) 0.0792(4) Uani 1 d . .
O4 O 0.3064(3) 0.5918(7) 0.4828(6) 0.0510(17) Uani 1 d . .
O1 O 0.5873(3) 0.9555(7) 0.4529(7) 0.0543(17) Uani 1 d . .
O3 O 0.3662(4) 0.3868(8) 0.4645(9) 0.075(2) Uani 1 d . .
N7 N 0.4752(3) 0.7041(8) 0.7117(7) 0.0466(18) Uani 1 d . .
O2 O 0.4058(4) 0.6058(10) 0.2679(7) 0.071(2) Uani 1 d . .
N2 N 0.5976(4) 0.8976(9) 0.2142(8) 0.054(2) Uani 1 d . .
H2 H 0.6093 0.9822 0.244 0.065 Uiso 1 calc . .
C12 C 0.6542(4) 0.9492(10) 0.0181(10) 0.047(3) Uani 1 d . .
H12 H 0.6434 1.0487 0.0266 0.056 Uiso 1 calc . .
C11 C 0.6313(5) 0.8474(10) 0.1052(9) 0.043(2) Uani 1 d . .
C2 C 0.5489(4) 0.8272(9) 0.2770(9) 0.042(2) Uani 1 d . .
C3 C 0.4994(4) 0.7438(9) 0.2286(8) 0.039(2) Uani 1 d . .
C1 C 0.5514(4) 0.8573(9) 0.4175(9) 0.038(2) Uani 1 d . .
C5 C 0.4164(4) 0.6119(9) 0.5287(9) 0.039(2) Uani 1 d . .
C6 C 0.4274(4) 0.6251(9) 0.6588(9) 0.041(2) Uani 1 d . .
C10 C 0.4592(4) 0.6864(9) 0.4490(9) 0.038(2) Uani 1 d . .
C4 C 0.4521(4) 0.6756(10) 0.3092(9) 0.044(2) Uani 1 d . .
C9 C 0.5088(4) 0.7751(9) 0.5027(9) 0.0382(19) Uani 1 d . .
C18 C 0.3827(5) 0.5548(10) 0.7555(10) 0.054(3) Uani 1 d . .
H18A H 0.4078 0.523 0.8286 0.065 Uiso 1 calc . .
H18B H 0.3618 0.4685 0.7188 0.065 Uiso 1 calc . .
C14 C 0.7083(4) 0.7587(11) -0.0920(8) 0.044(2) Uani 1 d . .
C13 C 0.6929(5) 0.9039(11) -0.0812(9) 0.052(3) Uani 1 d . .
H13 H 0.7083 0.9722 -0.1401 0.062 Uiso 1 calc . .
C19 C 0.3625(5) 0.5172(11) 0.4845(9) 0.046(2) Uani 1 d . .
C8 C 0.5160(4) 0.7786(10) 0.6348(8) 0.043(2) Uani 1 d . .
C15 C 0.6861(5) 0.6552(10) -0.0107(9) 0.048(2) Uani 1 d . .
H15 H 0.6967 0.5559 -0.0221 0.057 Uiso 1 calc . .
C16 C 0.6470(4) 0.6987(11) 0.0907(9) 0.048(2) Uani 1 d . .
H16 H 0.6315 0.6289 0.1481 0.058 Uiso 1 calc . .
C17 C 0.5695(5) 0.8590(11) 0.7037(10) 0.058(3) Uani 1 d . .
H17A H 0.558 0.9616 0.7123 0.086 Uiso 1 calc . .
H17B H 0.6093 0.8507 0.6565 0.086 Uiso 1 calc . .
H17C H 0.5752 0.8162 0.7863 0.086 Uiso 1 calc . .
C20 C 0.2486(6) 0.5078(15) 0.4542(12) 0.084(4) Uani 1 d . .
H20A H 0.2536 0.4599 0.3735 0.126 Uiso 1 calc . .
H20B H 0.2117 0.5731 0.4512 0.126 Uiso 1 calc . .
H20C H 0.2419 0.4345 0.5189 0.126 Uiso 1 calc . .
Cl1 Cl 0.75813(13) 0.7049(4) -0.2189(3) 0.0716(8) 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
Br1 C3 1.886(9) . ?
Br2 C18 1.947(9) . ?
O4 C19 1.333(11) . ?
O4 C20 1.441(13) . ?
O1 C1 1.211(10) . ?
O3 C19 1.199(11) . ?
N7 C6 1.335(11) . ?
N7 C8 1.346(11) . ?
O2 C4 1.221(11) . ?
N2 C2 1.356(12) . ?
N2 C11 1.416(12) . ?
N2 H2 0.86 . ?
C12 C13 1.376(14) . ?
C12 C11 1.381(13) . ?
C12 H12 0.93 . ?
C11 C16 1.390(14) . ?
C2 C3 1.364(12) . ?
C2 C1 1.507(13) . ?
C3 C4 1.430(12) . ?
C1 C9 1.456(12) . ?
C5 C10 1.389(12) . ?
C5 C6 1.394(13) . ?
C5 C19 1.475(13) . ?
C6 C18 1.511(13) . ?
C10 C9 1.414(12) . ?
C10 C4 1.483(13) . ?
C9 C8 1.400(12) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C14 C15 1.349(12) . ?
C14 C13 1.354(13) . ?
C14 Cl1 1.752(10) . ?
C13 H13 0.93 . ?
C8 C17 1.503(12) . ?
C15 C16 1.392(13) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?

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
C19 O4 C20 116.6(8) . . ?
C6 N7 C8 118.2(8) . . ?
C2 N2 C11 127.3(8) . . ?
C2 N2 H2 116.3 . . ?
C11 N2 H2 116.3 . . ?
C13 C12 C11 120.3(9) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C11 C16 119.4(9) . . ?
C12 C11 N2 119.5(8) . . ?
C16 C11 N2 120.8(9) . . ?
N2 C2 C3 128.7(9) . . ?
N2 C2 C1 111.7(8) . . ?
C3 C2 C1 119.5(8) . . ?
C2 C3 C4 121.5(8) . . ?
C2 C3 Br1 122.0(7) . . ?
C4 C3 Br1 116.3(6) . . ?
O1 C1 C9 123.3(9) . . ?
O1 C1 C2 117.0(9) . . ?
C9 C1 C2 119.6(8) . . ?
C10 C5 C6 116.8(8) . . ?
C10 C5 C19 124.4(8) . . ?
C6 C5 C19 118.8(9) . . ?
N7 C6 C5 125.1(9) . . ?
N7 C6 C18 112.9(9) . . ?
C5 C6 C18 121.9(9) . . ?
C5 C10 C9 119.2(8) . . ?
C5 C10 C4 120.4(8) . . ?
C9 C10 C4 120.4(8) . . ?
O2 C4 C3 122.6(9) . . ?
O2 C4 C10 117.7(9) . . ?
C3 C4 C10 119.6(8) . . ?
C8 C9 C10 119.1(8) . . ?
C8 C9 C1 122.6(8) . . ?
C10 C9 C1 118.3(8) . . ?
C6 C18 Br2 109.6(6) . . ?
C6 C18 H18A 109.8 . . ?
Br2 C18 H18A 109.8 . . ?
C6 C18 H18B 109.8 . . ?
Br2 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C15 C14 C13 122.6(9) . . ?
C15 C14 Cl1 119.4(7) . . ?
C13 C14 Cl1 118.0(7) . . ?
C14 C13 C12 119.1(9) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O3 C19 O4 123.3(9) . . ?
O3 C19 C5 125.3(9) . . ?
O4 C19 C5 111.0(8) . . ?
N7 C8 C9 121.5(8) . . ?
N7 C8 C17 113.9(8) . . ?
C9 C8 C17 124.6(9) . . ?
C14 C15 C16 119.1(9) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 119.4(9) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C8 C17 H17A 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C8 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C13 C12 C11 C16 -0.8(15) . . . . ?
C13 C12 C11 N2 173.1(8) . . . . ?
C2 N2 C11 C12 148.1(9) . . . . ?
C2 N2 C11 C16 -38.0(15) . . . . ?
C11 N2 C2 C3 -37.1(15) . . . . ?
C11 N2 C2 C1 146.3(9) . . . . ?
N2 C2 C3 C4 179.3(8) . . . . ?
C1 C2 C3 C4 -4.3(12) . . . . ?
N2 C2 C3 Br1 -6.6(13) . . . . ?
C1 C2 C3 Br1 169.8(6) . . . . ?
N2 C2 C1 O1 12.1(11) . . . . ?
C3 C2 C1 O1 -164.9(8) . . . . ?
N2 C2 C1 C9 -171.4(7) . . . . ?
C3 C2 C1 C9 11.7(11) . . . . ?
C8 N7 C6 C5 0.7(13) . . . . ?
C8 N7 C6 C18 -176.4(7) . . . . ?
C10 C5 C6 N7 0.5(13) . . . . ?
C19 C5 C6 N7 178.4(8) . . . . ?
C10 C5 C6 C18 177.4(8) . . . . ?
C19 C5 C6 C18 -4.7(13) . . . . ?
C6 C5 C10 C9 -2.7(11) . . . . ?
C19 C5 C10 C9 179.5(8) . . . . ?
C6 C5 C10 C4 178.5(8) . . . . ?
C19 C5 C10 C4 0.8(13) . . . . ?
C2 C3 C4 O2 176.8(9) . . . . ?
Br1 C3 C4 O2 2.3(12) . . . . ?
C2 C3 C4 C10 -4.3(13) . . . . ?
Br1 C3 C4 C10 -178.7(6) . . . . ?
C5 C10 C4 O2 3.6(13) . . . . ?
C9 C10 C4 O2 -175.1(8) . . . . ?
C5 C10 C4 C3 -175.4(8) . . . . ?
C9 C10 C4 C3 5.9(12) . . . . ?
C5 C10 C9 C8 3.7(12) . . . . ?
C4 C10 C9 C8 -177.5(7) . . . . ?
C5 C10 C9 C1 -177.3(7) . . . . ?
C4 C10 C9 C1 1.4(11) . . . . ?
O1 C1 C9 C8 -14.7(13) . . . . ?
C2 C1 C9 C8 169.0(8) . . . . ?
O1 C1 C9 C10 166.4(8) . . . . ?
C2 C1 C9 C10 -9.9(11) . . . . ?
N7 C6 C18 Br2 83.9(9) . . . . ?
C5 C6 C18 Br2 -93.3(9) . . . . ?
C15 C14 C13 C12 1.5(14) . . . . ?
Cl1 C14 C13 C12 -179.6(7) . . . . ?
C11 C12 C13 C14 -0.2(14) . . . . ?
C20 O4 C19 O3 -0.4(14) . . . . ?
C20 O4 C19 C5 -173.6(8) . . . . ?
C10 C5 C19 O3 90.2(13) . . . . ?
C6 C5 C19 O3 -87.4(13) . . . . ?
C10 C5 C19 O4 -96.7(10) . . . . ?
C6 C5 C19 O4 85.6(10) . . . . ?
C6 N7 C8 C9 0.3(12) . . . . ?
C6 N7 C8 C17 -177.8(8) . . . . ?
C10 C9 C8 N7 -2.5(13) . . . . ?
C1 C9 C8 N7 178.6(8) . . . . ?
C10 C9 C8 C17 175.4(8) . . . . ?
C1 C9 C8 C17 -3.5(14) . . . . ?
C13 C14 C15 C16 -1.7(14) . . . . ?
Cl1 C14 C15 C16 179.4(7) . . . . ?
C12 C11 C16 C15 0.7(15) . . . . ?
N2 C11 C16 C15 -173.2(8) . . . . ?
C14 C15 C16 C11 0.6(14) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_common            Isoquinoline
_chemical_melting_point          433-435
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_isonhclbr
_database_code_depnum_ccdc_archive 'CCDC 1528399'
_audit_update_record             
;
2017-01-18 deposited with the CCDC.
2017-02-23 downloaded from the CCDC.
;

_audit_creation_date             2016-10-05T09:24:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
'4-Carbomethoxy-7-(4-chlorophenylamino)-6-bromo-1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline '
_chemical_formula_moiety         'C19 H14 Br Cl N2 O4'
_chemical_formula_sum            'C19 H14 Br Cl N2 O4'
_chemical_formula_weight         449.68

#----------------------------------------------------------------------------#
#                   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                   14.560(3)
_cell_length_b                   10.207(2)
_cell_length_c                   25.110(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.18(3)
_cell_angle_gamma                90
_cell_volume                     3647.6(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6694
_cell_measurement_theta_max      3.520
_cell_measurement_theta_min      23.852
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_colour            ' orange'
_exptl_crystal_description       ' plate'
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.030
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.015
0 0 -1 0.015
1 -1 0 0.092
-1 0 0 0.036
1 0 0 0.099
0 1 0 0.077

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction. wR2(int) 
was 0.1322 before and 0.0960 after correction. The Ratio of minimum 
to maximum transmission is 0.4871. The λ/2 correction factor is 0.00150.
;


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

_diffrn_measurement_device_type  KappaCCD
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_radiation_probe          x-ray
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_ambient_temperature      298(2)
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_number            6491
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3565
_reflns_number_gt                2144
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_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)+(0.0281P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3565
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_restrained_S_all      0.938
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.084

#----------------------------------------------------------------------------#
#                   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
Br1 Br 0.88818(4) 0.16507(4) 0.28505(2) 0.05014(19) Uani 1 d . .
Cl Cl 1.16621(15) 0.40827(17) 0.48918(7) 0.1022(7) Uani 1 d . .
C17 C 0.8625(5) -0.5094(5) 0.3589(2) 0.0646(15) Uani 1 d . .
H17A H 0.863 -0.602 0.3524 0.097 Uiso 1 calc . .
H17B H 0.8069 -0.4865 0.3716 0.097 Uiso 1 calc . .
H17C H 0.917 -0.4856 0.3858 0.097 Uiso 1 calc . .
C20 C 0.7842(4) -0.1973(6) 0.07015(19) 0.0699(16) Uani 1 d . .
H20A H 0.7198 -0.1837 0.0523 0.105 Uiso 1 calc . .
H20B H 0.8129 -0.2579 0.0494 0.105 Uiso 1 calc . .
H20C H 0.8172 -0.1153 0.073 0.105 Uiso 1 calc . .
C19 C 0.8732(3) -0.2720(5) 0.15210(18) 0.0432(11) Uani 1 d . .
N7 N 0.8672(3) -0.5133(4) 0.26380(16) 0.0539(11) Uani 1 d . .
C4 C 0.8753(3) -0.0961(5) 0.24710(18) 0.0421(11) Uani 1 d . .
O4 O 0.7881(2) -0.2492(3) 0.12344(12) 0.0506(8) Uani 1 d . .
O3 O 0.9434(2) -0.2608(4) 0.13421(13) 0.0652(10) Uani 1 d . .
C5 C 0.8712(3) -0.3236(4) 0.20802(17) 0.0405(10) Uani 1 d . .
C10 C 0.8683(3) -0.2429(4) 0.25245(17) 0.0386(10) Uani 1 d . .
O1 O 0.8399(3) -0.2509(3) 0.39085(13) 0.0555(9) Uani 1 d . .
O2 O 0.8733(3) -0.0499(3) 0.20209(13) 0.0611(10) Uani 1 d . .
C9 C 0.8628(3) -0.3003(4) 0.30228(17) 0.0389(10) Uani 1 d . .
C3 C 0.8847(3) -0.0170(4) 0.29553(17) 0.0408(11) Uani 1 d . .
C8 C 0.8633(3) -0.4371(4) 0.3066(2) 0.0470(11) Uani 1 d . .
C11 C 0.9674(3) 0.0877(4) 0.41628(18) 0.0438(11) Uani 1 d . .
C12 C 0.9526(4) 0.1564(5) 0.4617(2) 0.0613(14) Uani 1 d . .
H12 H 0.9017 0.1351 0.4771 0.074 Uiso 1 calc . .
N2 N 0.9042(3) -0.0138(4) 0.39540(15) 0.0492(10) Uani 1 d . .
H2 H 0.8707 -0.0428 0.4173 0.059 Uiso 1 calc . .
C14 C 1.0898(4) 0.2815(5) 0.4623(2) 0.0568(14) Uani 1 d . .
C2 C 0.8887(3) -0.0721(4) 0.34582(17) 0.0394(10) Uani 1 d . .
C16 C 1.0471(4) 0.1129(5) 0.3960(2) 0.0491(12) Uani 1 d . .
H16 H 1.0592 0.0648 0.3667 0.059 Uiso 1 calc . .
C1 C 0.8613(3) -0.2139(4) 0.34883(17) 0.0382(10) Uani 1 d . .
C13 C 1.0125(5) 0.2553(6) 0.4841(2) 0.0703(16) Uani 1 d . .
H13 H 1.0011 0.3037 0.5134 0.084 Uiso 1 calc . .
C18 C 0.8744(4) -0.5532(5) 0.1711(2) 0.0638(15) Uani 1 d . .
H18A H 0.8734 -0.6412 0.1844 0.096 Uiso 1 calc . .
H18B H 0.9312 -0.5394 0.1582 0.096 Uiso 1 calc . .
H18C H 0.8212 -0.5395 0.1418 0.096 Uiso 1 calc . .
C15 C 1.1084(4) 0.2104(5) 0.4196(2) 0.0539(13) Uani 1 d . .
H15 H 1.1623 0.2276 0.4064 0.065 Uiso 1 calc . .
C6 C 0.8706(3) -0.4596(5) 0.21577(18) 0.0461(11) 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
Br1 C3 1.879(4) . ?
Cl C14 1.747(5) . ?
C17 C8 1.508(7) . ?
C20 O4 1.429(6) . ?
C19 O3 1.205(5) . ?
C19 O4 1.316(5) . ?
C19 C5 1.506(6) . ?
N7 C6 1.335(6) . ?
N7 C8 1.336(6) . ?
C4 O2 1.219(5) . ?
C4 C3 1.442(6) . ?
C4 C10 1.510(6) . ?
C5 C10 1.395(6) . ?
C5 C6 1.402(6) . ?
C10 C9 1.400(6) . ?
O1 C1 1.221(5) . ?
C9 C8 1.400(6) . ?
C9 C1 1.468(6) . ?
C3 C2 1.372(6) . ?
C11 C16 1.386(7) . ?
C11 C12 1.395(6) . ?
C11 N2 1.411(6) . ?
C12 C13 1.374(8) . ?
N2 C2 1.355(5) . ?
C14 C15 1.368(7) . ?
C14 C13 1.377(8) . ?
C2 C1 1.508(6) . ?
C16 C15 1.384(7) . ?
C18 C6 1.483(6) . ?

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
O3 C19 O4 123.6(4) . . ?
O3 C19 C5 124.4(4) . . ?
O4 C19 C5 111.8(4) . . ?
C6 N7 C8 120.2(4) . . ?
O2 C4 C3 123.0(4) . . ?
O2 C4 C10 118.5(4) . . ?
C3 C4 C10 118.5(4) . . ?
C19 O4 C20 115.1(4) . . ?
C10 C5 C6 118.2(4) . . ?
C10 C5 C19 123.3(4) . . ?
C6 C5 C19 118.5(4) . . ?
C5 C10 C9 119.0(4) . . ?
C5 C10 C4 120.1(4) . . ?
C9 C10 C4 120.9(4) . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 C1 118.2(4) . . ?
C8 C9 C1 122.6(4) . . ?
C2 C3 C4 121.6(4) . . ?
C2 C3 Br1 122.5(3) . . ?
C4 C3 Br1 115.9(3) . . ?
N7 C8 C9 121.2(4) . . ?
N7 C8 C17 115.1(4) . . ?
C9 C8 C17 123.6(4) . . ?
C16 C11 C12 119.6(5) . . ?
C16 C11 N2 122.0(4) . . ?
C12 C11 N2 118.1(4) . . ?
C13 C12 C11 120.6(5) . . ?
C2 N2 C11 129.2(4) . . ?
C15 C14 C13 121.5(5) . . ?
C15 C14 Cl 118.7(4) . . ?
C13 C14 Cl 119.8(4) . . ?
N2 C2 C3 129.2(4) . . ?
N2 C2 C1 111.7(4) . . ?
C3 C2 C1 118.6(4) . . ?
C15 C16 C11 119.3(4) . . ?
O1 C1 C9 123.5(4) . . ?
O1 C1 C2 117.3(4) . . ?
C9 C1 C2 119.2(4) . . ?
C12 C13 C14 118.8(5) . . ?
C14 C15 C16 120.0(5) . . ?
N7 C6 C5 122.3(4) . . ?
N7 C6 C18 115.7(4) . . ?
C5 C6 C18 122.0(4) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
_chemical_name_common            Isoquinoline
_chemical_melting_point          413-415
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
