# 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 2022

####################################################################### 
# 
# 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_exp_693
_database_code_depnum_ccdc_archive 'CCDC 2088459'
loop_
_audit_author_name
_audit_author_address
'Matija Gredicak'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-06-07 deposited with the CCDC.	2022-04-06 downloaded from the CCDC.
;

_audit_creation_date             2019-04-09T15:39:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C20 H13 Br Cl N O2'
_chemical_formula_weight         414.67
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_Int_Tables_number      92
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, -z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'-y, -x, -z+1/2'
'y, x, -z'
'y+1/2, -x+1/2, z+3/4'
'-y+1/2, x+1/2, z+1/4'

_cell_length_a                   11.3861(2)
_cell_length_b                   11.3861(2)
_cell_length_c                   27.0350(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3504.91(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7242
_cell_measurement_theta_min      4.202
_cell_measurement_theta_max      75.181

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

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             1664

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

_exptl_absorpt_coefficient_mu    4.708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.5865
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.4323
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0242369
_diffrn_orient_matrix_ub_12      0.1083464
_diffrn_orient_matrix_ub_13      0.0325677
_diffrn_orient_matrix_ub_21      -0.0442946
_diffrn_orient_matrix_ub_22      0.0806112
_diffrn_orient_matrix_ub_23      -0.0417829
_diffrn_orient_matrix_ub_31      -0.1255161
_diffrn_orient_matrix_ub_32      -0.0075075
_diffrn_orient_matrix_ub_33      0.021027
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.055
_diffrn_reflns_number            19652
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.213
_diffrn_reflns_theta_max         75.743
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_coverage         0.675
_reflns_number_total             3646
_reflns_number_gt                3425
_reflns_threshold_expression     'I > 2σ(I)'

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

_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  'SHELXL-2016/4 (Sheldrick, 2016)'

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

_atom_sites_solution_hydrogens   mixed

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+1.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00111(14)
_refine_ls_number_reflns         3646
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.102
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1307 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.031(9)
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'
Br Br -0.6763 1.2805 '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_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
C2 C 0.2440(3) 0.9458(3) 0.04207(13) 0.0446(8) Uani 1 1 d . . . . .
C3 C 0.3170(3) 0.9775(3) -0.00119(13) 0.0431(7) Uani 1 1 d . . . . .
C4 C 0.3155(4) 1.0791(4) -0.03016(16) 0.0563(10) Uani 1 1 d . . . . .
H4 H 0.263479 1.140001 -0.023481 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3927(5) 1.0859(4) -0.06850(16) 0.0627(12) Uani 1 1 d . . . . .
H5 H 0.394916 1.153543 -0.087735 0.075 Uiso 1 1 calc R U . . .
C6 C 0.4680(4) 0.9940(4) -0.07942(15) 0.0575(10) Uani 1 1 d . . . . .
H6 H 0.519533 1.000752 -0.105968 0.069 Uiso 1 1 calc R U . . .
C7 C 0.4679(4) 0.8919(4) -0.05140(14) 0.0516(9) Uani 1 1 d . . . . .
H7 H 0.517115 0.829535 -0.0593 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3923(3) 0.8856(3) -0.01127(12) 0.0399(7) Uani 1 1 d . . . . .
C9 C 0.3718(3) 0.7857(3) 0.02522(11) 0.0380(6) Uani 1 1 d . . . . .
C10 C 0.4778(3) 0.7536(3) 0.05757(12) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.4620(3) 0.6740(3) 0.09657(13) 0.0439(7) Uani 1 1 d . . . . .
C12 C 0.5550(4) 0.6448(4) 0.12719(15) 0.0527(9) Uani 1 1 d . . . . .
H12 H 0.543485 0.591637 0.152851 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6645(4) 0.6937(4) 0.12007(15) 0.0587(10) Uani 1 1 d . . . . .
H13 H 0.726872 0.674251 0.14073 0.07 Uiso 1 1 calc R U . . .
C14 C 0.6798(4) 0.7719(4) 0.08183(14) 0.0539(9) Uani 1 1 d . . . . .
C15 C 0.5882(4) 0.8024(3) 0.05077(14) 0.0477(8) Uani 1 1 d . . . . .
H15 H 0.600698 0.855724 0.025261 0.057 Uiso 1 1 calc R U . . .
C16 C 0.3272(3) 0.6784(3) -0.00376(11) 0.0374(6) Uani 1 1 d . . . . .
C17 C 0.2082(3) 0.6569(3) -0.00999(13) 0.0453(8) Uani 1 1 d . . . . .
H17 H 0.153658 0.706574 0.00477 0.054 Uiso 1 1 calc R U . . .
C18 C 0.1697(3) 0.5625(4) -0.03790(15) 0.0493(8) Uani 1 1 d . . . . .
H18 H 0.089782 0.548608 -0.042072 0.059 Uiso 1 1 calc R U . . .
C19 C 0.2514(3) 0.4896(3) -0.05935(13) 0.0437(8) Uani 1 1 d . . . . .
C20 C 0.3695(3) 0.5091(4) -0.05416(15) 0.0495(8) Uani 1 1 d . . . . .
H20 H 0.423697 0.458908 -0.068844 0.059 Uiso 1 1 calc R U . . .
C21 C 0.4069(3) 0.6050(3) -0.02661(14) 0.0464(8) Uani 1 1 d . . . . .
H21 H 0.486829 0.619952 -0.023518 0.056 Uiso 1 1 calc R U . . .
N1 N 0.2793(3) 0.8379(3) 0.05576(11) 0.0444(6) Uani 1 1 d . . . . .
O2 O 0.1665(3) 1.0038(3) 0.06216(11) 0.0612(7) Uani 1 1 d . . . . .
O11 O 0.3528(3) 0.6292(3) 0.10314(11) 0.0531(7) Uani 1 1 d . . . . .
CL1 Cl 0.20369(10) 0.36864(9) -0.09320(4) 0.0601(3) Uani 1 1 d . . . . .
BR1 Br 0.83059(6) 0.84090(8) 0.07242(2) 0.0950(3) Uani 1 1 d . . . . .
H1 H 0.255(5) 0.805(5) 0.078(2) 0.070(17) Uiso 1 1 d . . . . .
H11 H 0.359(6) 0.594(6) 0.124(3) 0.10(2) Uiso 1 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
C2 O2 1.229(5) . ?
C2 N1 1.345(5) . ?
C2 C3 1.479(5) . ?
C3 C8 1.381(5) . ?
C3 C4 1.396(5) . ?
C4 C5 1.361(7) . ?
C4 H4 0.93 . ?
C5 C6 1.385(7) . ?
C5 H5 0.93 . ?
C6 C7 1.387(6) . ?
C6 H6 0.93 . ?
C7 C8 1.387(5) . ?
C7 H7 0.93 . ?
C8 C9 1.523(5) . ?
C9 N1 1.465(4) . ?
C9 C10 1.534(5) . ?
C9 C16 1.537(5) . ?
C10 C15 1.387(5) . ?
C10 C11 1.402(5) . ?
C11 O11 1.355(5) . ?
C11 C12 1.384(5) . ?
C12 C13 1.380(7) . ?
C12 H12 0.93 . ?
C13 C14 1.375(6) . ?
C13 H13 0.93 . ?
C14 C15 1.383(6) . ?
C14 BR1 1.905(4) . ?
C15 H15 0.93 . ?
C16 C21 1.380(5) . ?
C16 C17 1.387(5) . ?
C17 C18 1.385(5) . ?
C17 H17 0.93 . ?
C18 C19 1.375(6) . ?
C18 H18 0.93 . ?
C19 C20 1.370(6) . ?
C19 CL1 1.740(4) . ?
C20 C21 1.389(5) . ?
C20 H20 0.93 . ?
C21 H21 0.93 . ?
N1 H1 0.77(5) . ?
O11 H11 0.71(7) . ?

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
O2 C2 N1 125.7(4) . . ?
O2 C2 C3 128.4(4) . . ?
N1 C2 C3 105.9(3) . . ?
C8 C3 C4 121.7(4) . . ?
C8 C3 C2 108.6(3) . . ?
C4 C3 C2 129.7(4) . . ?
C5 C4 C3 117.8(4) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 118.2(4) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C3 C8 C7 120.0(3) . . ?
C3 C8 C9 110.1(3) . . ?
C7 C8 C9 129.8(3) . . ?
N1 C9 C8 99.9(3) . . ?
N1 C9 C10 110.0(3) . . ?
C8 C9 C10 115.3(3) . . ?
N1 C9 C16 111.8(3) . . ?
C8 C9 C16 108.3(3) . . ?
C10 C9 C16 111.2(3) . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C9 122.8(3) . . ?
C11 C10 C9 118.8(3) . . ?
O11 C11 C12 122.2(3) . . ?
O11 C11 C10 117.3(3) . . ?
C12 C11 C10 120.4(4) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 118.7(4) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 121.6(4) . . ?
C13 C14 BR1 118.7(3) . . ?
C15 C14 BR1 119.7(3) . . ?
C14 C15 C10 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C21 C16 C17 118.7(3) . . ?
C21 C16 C9 119.5(3) . . ?
C17 C16 C9 121.7(3) . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C20 C19 C18 121.5(4) . . ?
C20 C19 CL1 119.2(3) . . ?
C18 C19 CL1 119.2(3) . . ?
C19 C20 C21 118.9(3) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C16 C21 C20 121.0(3) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C2 N1 C9 115.5(3) . . ?
C2 N1 H1 124(4) . . ?
C9 N1 H1 121(5) . . ?
C11 O11 H11 103(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
O2 C2 C3 C8 -179.6(4) . . . . ?
N1 C2 C3 C8 0.3(4) . . . . ?
O2 C2 C3 C4 -0.9(7) . . . . ?
N1 C2 C3 C4 179.0(4) . . . . ?
C8 C3 C4 C5 -1.2(6) . . . . ?
C2 C3 C4 C5 -179.7(4) . . . . ?
C3 C4 C5 C6 1.8(7) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C5 C6 C7 C8 -1.6(6) . . . . ?
C4 C3 C8 C7 -0.8(6) . . . . ?
C2 C3 C8 C7 177.9(3) . . . . ?
C4 C3 C8 C9 -178.2(3) . . . . ?
C2 C3 C8 C9 0.5(4) . . . . ?
C6 C7 C8 C3 2.2(6) . . . . ?
C6 C7 C8 C9 179.0(4) . . . . ?
C3 C8 C9 N1 -1.1(4) . . . . ?
C7 C8 C9 N1 -178.1(4) . . . . ?
C3 C8 C9 C10 -118.9(3) . . . . ?
C7 C8 C9 C10 64.1(5) . . . . ?
C3 C8 C9 C16 116.0(3) . . . . ?
C7 C8 C9 C16 -61.1(5) . . . . ?
N1 C9 C10 C15 -118.7(4) . . . . ?
C8 C9 C10 C15 -6.7(5) . . . . ?
C16 C9 C10 C15 116.9(4) . . . . ?
N1 C9 C10 C11 59.5(4) . . . . ?
C8 C9 C10 C11 171.4(3) . . . . ?
C16 C9 C10 C11 -64.9(4) . . . . ?
C15 C10 C11 O11 178.7(3) . . . . ?
C9 C10 C11 O11 0.4(5) . . . . ?
C15 C10 C11 C12 -0.4(5) . . . . ?
C9 C10 C11 C12 -178.6(3) . . . . ?
O11 C11 C12 C13 -178.7(4) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C12 C13 C14 BR1 179.3(3) . . . . ?
C13 C14 C15 C10 -0.3(6) . . . . ?
BR1 C14 C15 C10 -179.4(3) . . . . ?
C11 C10 C15 C14 0.4(6) . . . . ?
C9 C10 C15 C14 178.5(3) . . . . ?
N1 C9 C16 C21 -167.3(3) . . . . ?
C8 C9 C16 C21 83.6(4) . . . . ?
C10 C9 C16 C21 -44.0(4) . . . . ?
N1 C9 C16 C17 16.4(4) . . . . ?
C8 C9 C16 C17 -92.7(4) . . . . ?
C10 C9 C16 C17 139.7(3) . . . . ?
C21 C16 C17 C18 1.1(6) . . . . ?
C9 C16 C17 C18 177.4(3) . . . . ?
C16 C17 C18 C19 0.2(6) . . . . ?
C17 C18 C19 C20 -0.7(6) . . . . ?
C17 C18 C19 CL1 178.4(3) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
CL1 C19 C20 C21 -179.3(3) . . . . ?
C17 C16 C21 C20 -1.9(6) . . . . ?
C9 C16 C21 C20 -178.3(3) . . . . ?
C19 C20 C21 C16 1.5(6) . . . . ?
O2 C2 N1 C9 178.8(4) . . . . ?
C3 C2 N1 C9 -1.1(4) . . . . ?
C8 C9 N1 C2 1.4(4) . . . . ?
C10 C9 N1 C2 123.0(3) . . . . ?
C16 C9 N1 C2 -113.0(3) . . . . ?

# 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
