# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_br4q
_database_code_depnum_ccdc_archive 'CCDC 2105667'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2019-05-29T11:16:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C6 Br4 O2, 2(C6 H9 N2), 2(I)'
_chemical_formula_sum            'C18 H18 Br4 I2 N4 O2'
_chemical_formula_weight         895.76

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a                   7.0570(4)
_cell_length_b                   12.6851(6)
_cell_length_c                   14.8883(9)
_cell_angle_alpha                80.126(4)
_cell_angle_beta                 77.986(5)
_cell_angle_gamma                76.607(5)
_cell_volume                     1257.45(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    6376
_cell_measurement_theta_min      3.6010
_cell_measurement_theta_max      75.3170
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.366
_exptl_crystal_F_000             832.0
_exptl_absorpt_coefficient_mu    27.282
_exptl_absorpt_correction_T_min  0.32695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            11628
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         76.311
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             5191
_reflns_number_gt                4916
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1452
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_refine_ls_number_reflns         5191
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1267P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.635
_refine_diff_density_min         -3.271
_refine_diff_density_rms         0.326
_refine_ls_extinction_method     none
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'
I I -0.3257 6.8362 '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'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.36540(6) 0.17922(3) 0.79304(2) 0.02103(14) Uani d 1 . . I
I2 1.00766(6) 0.68119(3) 0.67831(2) 0.01949(14) Uani d 1 . . I
Br1 0.52934(10) 0.56180(5) 0.59761(4) 0.02363(17) Uani d 1 . . Br
Br2 0.79005(10) 0.30259(5) 0.62625(4) 0.02411(17) Uani d 1 . . Br
O1 0.7860(7) 0.6999(4) 0.4647(3) 0.0244(9) Uani d 1 . . O
C1 0.8840(9) 0.6105(5) 0.4837(4) 0.0187(10) Uani d 1 . . C
C2 0.7966(9) 0.5203(4) 0.5432(4) 0.0181(10) Uani d 1 . . C
C3 0.9011(9) 0.4183(4) 0.5555(4) 0.0191(11) Uani d 1 . . C
Br3 0.79434(9) 0.83925(4) 0.85418(4) 0.01822(16) Uani d 1 . . Br
Br4 0.91773(9) 1.07335(4) 0.88912(4) 0.01882(16) Uani d 1 . . Br
O2 0.3978(7) 0.8236(3) 0.9647(3) 0.0253(9) Uani d 1 . . O
C4 0.4467(10) 0.9034(4) 0.9832(4) 0.0177(10) Uani d 1 . . C
C5 0.6387(9) 0.9331(4) 0.9383(4) 0.0148(10) Uani d 1 . . C
C6 0.6877(9) 1.0253(4) 0.9506(4) 0.0180(10) Uani d 1 . . C
N1 0.6937(8) 0.0782(4) 0.3637(4) 0.0212(10) Uani d 1 . . N
N2 0.7388(8) -0.0178(4) 0.6382(4) 0.0229(10) Uani d 1 . . N
H2B 0.807247 -0.080947 0.655042 0.027 Uiso calc 1 . . H
H2A 0.678296 0.024849 0.678925 0.027 Uiso calc 1 . . H
C7 0.8048(10) -0.0210(5) 0.3888(5) 0.0232(12) Uani d 1 . . C
H7 0.867698 -0.066745 0.344123 0.028 Uiso calc 1 . . H
C8 0.8247(10) -0.0543(5) 0.4796(4) 0.0224(11) Uani d 1 . . C
H8 0.902617 -0.121928 0.496341 0.027 Uiso calc 1 . . H
C9 0.7264(9) 0.0145(5) 0.5477(4) 0.0222(11) Uani d 1 . . C
C10 0.6105(9) 0.1166(4) 0.5190(4) 0.0219(11) Uani d 1 . . C
H10 0.543989 0.164203 0.561688 0.026 Uiso calc 1 . . H
C11 0.5981(10) 0.1442(5) 0.4274(4) 0.0227(11) Uani d 1 . . C
H11 0.520701 0.211066 0.408464 0.027 Uiso calc 1 . . H
C12 0.6780(10) 0.1151(5) 0.2649(4) 0.0258(12) Uani d 1 . . C
H12A 0.558164 0.168633 0.260924 0.039 Uiso calc 1 . . H
H12C 0.676176 0.053702 0.235521 0.039 Uiso calc 1 . . H
H12B 0.789517 0.146714 0.23446 0.039 Uiso calc 1 . . H
N3 0.2113(8) 0.5613(4) 1.0858(3) 0.0200(9) Uani d 1 . . N
N4 0.2746(9) 0.4640(4) 0.8295(4) 0.0247(11) Uani d 1 . . N
H4B 0.243424 0.511653 0.78369 0.03 Uiso calc 1 . . H
H4A 0.316767 0.396297 0.821886 0.03 Uiso calc 1 . . H
C13 0.2799(9) 0.4546(5) 1.0740(4) 0.0214(11) Uani d 1 . . C
H13 0.31074 0.403983 1.124588 0.026 Uiso calc 1 . . H
C14 0.3049(9) 0.4195(4) 0.9899(4) 0.0194(11) Uani d 1 . . C
H14 0.353043 0.345849 0.983719 0.023 Uiso calc 1 . . H
C15 0.2578(9) 0.4947(4) 0.9119(4) 0.0199(11) Uani d 1 . . C
C16 0.1888(10) 0.6055(5) 0.9270(5) 0.0230(12) Uani d 1 . . C
H16 0.15805 0.658057 0.877481 0.028 Uiso calc 1 . . H
C17 0.1667(9) 0.6368(4) 1.0117(4) 0.0203(11) Uani d 1 . . C
H17 0.120844 0.710054 1.019707 0.024 Uiso calc 1 . . H
C18 0.1934(11) 0.5980(5) 1.1760(5) 0.0289(13) Uani d 1 . . C
H18A 0.215721 0.535636 1.222023 0.043 Uiso calc 1 . . H
H18B 0.063105 0.640739 1.192809 0.043 Uiso calc 1 . . H
H18C 0.289792 0.641782 1.172281 0.043 Uiso calc 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.882(6) ?
Br2 C3 . 1.880(6) ?
O1 C1 . 1.205(8) ?
C1 C3 2_766 1.491(9) ?
C1 C2 . 1.491(8) ?
C2 C3 . 1.336(8) ?
Br3 C5 . 1.877(5) ?
Br4 C6 . 1.869(6) ?
O2 C4 . 1.232(7) ?
C4 C6 2_677 1.486(8) ?
C4 C5 . 1.482(8) ?
C5 C6 . 1.345(8) ?
N1 C11 . 1.342(8) ?
N1 C7 . 1.357(8) ?
N1 C12 . 1.483(8) ?
N2 C9 . 1.355(8) ?
N2 H2B . 0.86 ?
N2 H2A . 0.86 ?
C7 C8 . 1.372(9) ?
C7 H7 . 0.93 ?
C8 C9 . 1.415(9) ?
C8 H8 . 0.93 ?
C9 C10 . 1.413(8) ?
C10 C11 . 1.364(9) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12C . 0.96 ?
C12 H12B . 0.96 ?
N3 C13 . 1.357(8) ?
N3 C17 . 1.369(7) ?
N3 C18 . 1.468(8) ?
N4 C15 . 1.323(8) ?
N4 H4B . 0.86 ?
N4 H4A . 0.86 ?
C13 C14 . 1.364(9) ?
C13 H13 . 0.93 ?
C14 C15 . 1.416(8) ?
C14 H14 . 0.93 ?
C15 C16 . 1.417(8) ?
C16 C17 . 1.355(9) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 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
O1 C1 C3 121.6(5) . 2_766 ?
O1 C1 C2 122.4(6) . . ?
C3 C1 C2 115.9(5) 2_766 . ?
C3 C2 C1 122.0(6) . . ?
C3 C2 Br1 123.3(5) . . ?
C1 C2 Br1 114.7(4) . . ?
C2 C3 C1 121.9(5) . 2_766 ?
C2 C3 Br2 122.5(5) . . ?
C1 C3 Br2 115.5(4) 2_766 . ?
O2 C4 C6 120.9(6) . 2_677 ?
O2 C4 C5 121.1(5) . . ?
C6 C4 C5 118.0(5) 2_677 . ?
C6 C5 C4 122.3(5) . . ?
C6 C5 Br3 123.0(5) . . ?
C4 C5 Br3 114.4(4) . . ?
C5 C6 C4 119.6(5) . 2_677 ?
C5 C6 Br4 124.6(5) . . ?
C4 C6 Br4 115.8(4) 2_677 . ?
C11 N1 C7 120.7(5) . . ?
C11 N1 C12 119.3(5) . . ?
C7 N1 C12 120.1(5) . . ?
C9 N2 H2B 120 . . ?
C9 N2 H2A 120 . . ?
H2B N2 H2A 120 . . ?
N1 C7 C8 120.4(6) . . ?
N1 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.8(5) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
N2 C9 C8 121.0(5) . . ?
N2 C9 C10 120.9(6) . . ?
C8 C9 C10 118.1(6) . . ?
C11 C10 C9 118.7(6) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 122.3(5) . . ?
N1 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
C13 N3 C17 119.8(5) . . ?
C13 N3 C18 120.9(5) . . ?
C17 N3 C18 119.3(5) . . ?
C15 N4 H4B 120 . . ?
C15 N4 H4A 120 . . ?
H4B N4 H4A 120 . . ?
C14 C13 N3 121.8(5) . . ?
C14 C13 H13 119.1 . . ?
N3 C13 H13 119.1 . . ?
C13 C14 C15 120.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
N4 C15 C16 121.5(6) . . ?
N4 C15 C14 122.3(5) . . ?
C16 C15 C14 116.2(6) . . ?
C17 C16 C15 121.6(5) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 N3 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
N3 C17 H17 119.8 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C1 C2 C3 172.3(6) . . . . ?
C3 C1 C2 C3 -4.3(9) 2_766 . . . ?
O1 C1 C2 Br1 -7.1(7) . . . . ?
C3 C1 C2 Br1 176.3(4) 2_766 . . . ?
C1 C2 C3 C1 4.5(10) . . . 2_766 ?
Br1 C2 C3 C1 -176.1(4) . . . 2_766 ?
C1 C2 C3 Br2 -177.4(4) . . . . ?
Br1 C2 C3 Br2 2.0(8) . . . . ?
O2 C4 C5 C6 173.6(5) . . . . ?
C6 C4 C5 C6 -4.7(9) 2_677 . . . ?
O2 C4 C5 Br3 -0.4(7) . . . . ?
C6 C4 C5 Br3 -178.8(4) 2_677 . . . ?
C4 C5 C6 C4 4.8(9) . . . 2_677 ?
Br3 C5 C6 C4 178.3(4) . . . 2_677 ?
C4 C5 C6 Br4 -175.0(4) . . . . ?
Br3 C5 C6 Br4 -1.5(7) . . . . ?
C11 N1 C7 C8 -1.5(9) . . . . ?
C12 N1 C7 C8 178.1(6) . . . . ?
N1 C7 C8 C9 1.0(10) . . . . ?
C7 C8 C9 N2 178.0(6) . . . . ?
C7 C8 C9 C10 -0.3(9) . . . . ?
N2 C9 C10 C11 -178.2(6) . . . . ?
C8 C9 C10 C11 0.2(9) . . . . ?
C7 N1 C11 C10 1.4(10) . . . . ?
C12 N1 C11 C10 -178.2(6) . . . . ?
C9 C10 C11 N1 -0.7(10) . . . . ?
C17 N3 C13 C14 -0.5(9) . . . . ?
C18 N3 C13 C14 -177.4(6) . . . . ?
N3 C13 C14 C15 -0.4(9) . . . . ?
C13 C14 C15 N4 -178.2(6) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
N4 C15 C16 C17 178.3(6) . . . . ?
C14 C15 C16 C17 -1.0(9) . . . . ?
C15 C16 C17 N3 0.2(10) . . . . ?
C13 N3 C17 C16 0.6(9) . . . . ?
C18 N3 C17 C16 177.6(6) . . . . ?



# 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
####################################################################### 
# 
# 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_n-mepycl4q-dija-100k
_database_code_depnum_ccdc_archive 'CCDC 2105669'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2016-12-07T15:08:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 Br4 I2 N2 O2'
_chemical_formula_sum            'C18 H16 Br4 Cl0 I2 N2 O2'
_chemical_formula_weight         865.77

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.4807(5)
_cell_length_b                   9.1376(4)
_cell_length_c                   17.3524(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.217(3)
_cell_angle_gamma                90
_cell_volume                     2454.05(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5648
_cell_measurement_theta_min      3.7836
_cell_measurement_theta_max      75.7053
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    2.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    27.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.20521
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            13451
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_theta_min         5.1
_diffrn_reflns_theta_max         75.89
_diffrn_reflns_theta_full        75.89
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       14

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2sigma(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.
;
_reflns_number_total             5063
_reflns_number_gt                4451
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.056
_refine_ls_wR_factor_ref         0.1565
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.047
_refine_ls_number_reflns         5063
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0966P)²+10.8647P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.564
_refine_diff_density_min         -2.28
_refine_diff_density_rms         0.271
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0 0 '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'
Cl Cl 0.3639 0.7018 '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'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.34853(3) 0.77558(6) 0.84926(2) 0.02629(16) Uani d . 1 . . I
I2 1.12623(3) 1.22696(7) 1.14409(3) 0.03220(17) Uani d . 1 . . I
Br1 0.55375(5) 0.86499(10) 0.92886(4) 0.0270(2) Uani d . 1 . . Br
Br2 0.68366(6) 1.09724(11) 0.83062(4) 0.0317(2) Uani d . 1 . . Br
Br3 0.93027(5) 1.08148(10) 1.07671(4) 0.0273(2) Uani d . 1 . . Br
Br4 0.80643(5) 0.84026(10) 1.17262(4) 0.0268(2) Uani d . 1 . . Br
O1 0.6477(4) 0.7729(8) 1.0746(3) 0.0355(14) Uani d . 1 . . O
O2 0.8317(4) 1.1818(8) 0.9358(3) 0.0347(13) Uani d . 1 . . O
C1 0.6907(5) 0.8640(9) 1.0429(4) 0.0261(16) Uani d . 1 . . C
C2 0.6625(5) 0.9293(9) 0.9674(4) 0.0229(14) Uani d . 1 . . C
C3 0.7122(5) 1.0212(9) 0.9290(4) 0.0262(15) Uani d . 1 . . C
C4 0.7940(5) 1.0808(10) 0.9644(4) 0.0280(16) Uani d . 1 . . C
C5 0.8231(5) 1.0107(9) 1.0375(4) 0.0256(15) Uani d . 1 . . C
C6 0.7747(5) 0.9164(9) 1.0751(4) 0.0243(15) Uani d . 1 . . C
N1 0.4204(4) 0.0537(9) 0.6898(3) 0.0292(14) Uani d . 1 . . N
C7 0.4836(5) -0.0165(10) 0.6549(5) 0.0324(17) Uani d . 1 . . C
H7 0.5393 -0.0137 0.6758 0.039 Uiso calc R 1 . . H
C8 0.4676(6) -0.0932(11) 0.5881(5) 0.0374(19) Uani d . 1 . . C
H8 0.5122 -0.1425 0.564 0.045 Uiso calc R 1 . . H
C9 0.3846(7) -0.0968(13) 0.5567(5) 0.046(2) Uani d . 1 . . C
H9 0.3727 -0.1487 0.5116 0.055 Uiso calc R 1 . . H
C10 0.3196(6) -0.0218(15) 0.5937(5) 0.047(3) Uani d . 1 . . C
H10 0.2634 -0.0227 0.5737 0.057 Uiso calc R 1 . . H
C11 0.3394(6) 0.0551(12) 0.6611(5) 0.037(2) Uani d . 1 . . C
H11 0.2966 0.1071 0.6861 0.045 Uiso calc R 1 . . H
C12 0.4386(6) 0.1377(12) 0.7607(4) 0.037(2) Uani d . 1 . . C
H12C 0.3861 0.1808 0.7784 0.056 Uiso calc R 1 . . H
H12B 0.4797 0.2135 0.7502 0.056 Uiso calc R 1 . . H
H12A 0.4619 0.0735 0.7997 0.056 Uiso calc R 1 . . H
N2 0.0859(10) 0.5404(15) 0.8219(7) 0.094(6) Uani d . 1 . . N
C13 0.1415(7) 0.5316(13) 0.8943(10) 0.066(4) Uani d . 1 . . C
H13 0.1925 0.5841 0.9014 0.08 Uiso calc R 1 . . H
C14 0.1097(11) 0.4396(14) 0.9478(6) 0.062(4) Uani d . 1 . . C
H14 0.14 0.4279 0.9943 0.075 Uiso calc R 1 . . H
C15 0.0400(11) 0.3688(14) 0.9370(10) 0.073(4) Uani d D 1 . . C
H15 0.0243 0.3015 0.9744 0.087 Uiso calc R 1 . . H
C16 -0.0088(11) 0.3836(17) 0.8795(12) 0.082(5) Uani d . 1 . . C
H16 -0.0622 0.337 0.8794 0.098 Uiso calc R 1 . . H
C17 0.0087(7) 0.452(2) 0.8266(7) 0.085(6) Uani d D 1 . . C
H17 -0.029 0.45 0.7842 0.101 Uiso calc R 1 . . H
C18 0.1044(10) 0.6531(17) 0.7622(8) 0.069(4) Uani d . 1 . . C
H18C 0.1599 0.6964 0.773 0.103 Uiso calc R 1 . . H
H18B 0.0607 0.7275 0.7629 0.103 Uiso calc R 1 . . H
H18A 0.1047 0.6078 0.7123 0.103 Uiso calc R 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.893(7) ?
Br2 C3 . 1.887(7) ?
Br3 C5 . 1.894(8) ?
Br4 C6 . 1.885(7) ?
O1 C1 . 1.205(10) ?
O2 C4 . 1.205(11) ?
C1 C6 . 1.484(11) ?
C1 C2 . 1.497(10) ?
C2 C3 . 1.327(11) ?
C3 C4 . 1.498(11) ?
C4 C5 . 1.483(10) ?
C5 C6 . 1.323(12) ?
N1 C7 . 1.326(11) ?
N1 C11 . 1.339(11) ?
N1 C12 . 1.472(11) ?
C7 C8 . 1.373(14) ?
C7 H7 . 0.93 ?
C8 C9 . 1.385(15) ?
C8 H8 . 0.93 ?
C9 C10 . 1.386(15) ?
C9 H9 . 0.93 ?
C10 C11 . 1.394(14) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12C . 0.96 ?
C12 H12B . 0.96 ?
C12 H12A . 0.96 ?
N2 C17 . 1.45(2) ?
N2 C18 . 1.493(17) ?
N2 C13 . 1.51(2) ?
C13 C14 . 1.35(2) ?
C13 H13 . 0.93 ?
C14 C15 . 1.27(2) ?
C14 H14 . 0.93 ?
C15 C16 . 1.25(2) ?
C15 H15 . 0.93 ?
C16 C17 . 1.15(2) ?
C16 H16 . 0.93 ?
C17 H17 . 0.93 ?
C18 H18C . 0.96 ?
C18 H18B . 0.96 ?
C18 H18A . 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
O1 C1 C6 122.6(7) . . ?
O1 C1 C2 121.5(7) . . ?
C6 C1 C2 115.9(7) . . ?
C3 C2 C1 122.1(7) . . ?
C3 C2 Br1 122.7(6) . . ?
C1 C2 Br1 115.2(6) . . ?
C2 C3 C4 121.2(7) . . ?
C2 C3 Br2 124.1(6) . . ?
C4 C3 Br2 114.6(6) . . ?
O2 C4 C5 122.9(8) . . ?
O2 C4 C3 121.5(7) . . ?
C5 C4 C3 115.6(7) . . ?
C6 C5 C4 122.6(7) . . ?
C6 C5 Br3 123.1(6) . . ?
C4 C5 Br3 114.1(6) . . ?
C5 C6 C1 121.7(6) . . ?
C5 C6 Br4 122.9(6) . . ?
C1 C6 Br4 115.3(5) . . ?
C7 N1 C11 121.9(8) . . ?
C7 N1 C12 120.3(8) . . ?
C11 N1 C12 117.8(8) . . ?
N1 C7 C8 120.8(8) . . ?
N1 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 119.6(8) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.8(9) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 119.3(9) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 119.6(8) . . ?
N1 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N1 C12 H12C 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12C C12 H12B 109.5 . . ?
N1 C12 H12A 109.5 . . ?
H12C C12 H12A 109.5 . . ?
H12B C12 H12A 109.5 . . ?
C17 N2 C18 126.6(15) . . ?
C17 N2 C13 112.3(10) . . ?
C18 N2 C13 120.0(15) . . ?
C14 C13 N2 113.2(11) . . ?
C14 C13 H13 123.4 . . ?
N2 C13 H13 123.4 . . ?
C15 C14 C13 122.5(13) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C16 C15 C14 124.2(15) . . ?
C16 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
C17 C16 C15 123.4(16) . . ?
C17 C16 H16 118.3 . . ?
C15 C16 H16 118.3 . . ?
C16 C17 N2 124.0(13) . . ?
C16 C17 H17 118 . . ?
N2 C17 H17 118 . . ?
N2 C18 H18C 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
N2 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 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
O1 C1 C2 C3 -174.7(8) . . . . ?
C6 C1 C2 C3 4.2(11) . . . . ?
O1 C1 C2 Br1 2.7(11) . . . . ?
C6 C1 C2 Br1 -178.3(5) . . . . ?
C1 C2 C3 C4 -8.6(12) . . . . ?
Br1 C2 C3 C4 174.2(6) . . . . ?
C1 C2 C3 Br2 175.7(6) . . . . ?
Br1 C2 C3 Br2 -1.5(10) . . . . ?
C2 C3 C4 O2 -167.4(8) . . . . ?
Br2 C3 C4 O2 8.6(11) . . . . ?
C2 C3 C4 C5 10.7(11) . . . . ?
Br2 C3 C4 C5 -173.2(5) . . . . ?
O2 C4 C5 C6 168.9(9) . . . . ?
C3 C4 C5 C6 -9.2(11) . . . . ?
O2 C4 C5 Br3 -5.5(11) . . . . ?
C3 C4 C5 Br3 176.4(5) . . . . ?
C4 C5 C6 C1 5.6(12) . . . . ?
Br3 C5 C6 C1 179.5(6) . . . . ?
C4 C5 C6 Br4 -174.0(6) . . . . ?
Br3 C5 C6 Br4 -0.1(10) . . . . ?
O1 C1 C6 C5 176.3(8) . . . . ?
C2 C1 C6 C5 -2.6(11) . . . . ?
O1 C1 C6 Br4 -4.1(11) . . . . ?
C2 C1 C6 Br4 177.0(5) . . . . ?
C11 N1 C7 C8 -1.2(13) . . . . ?
C12 N1 C7 C8 -179.0(8) . . . . ?
N1 C7 C8 C9 0.3(14) . . . . ?
C7 C8 C9 C10 0.3(16) . . . . ?
C8 C9 C10 C11 0.1(17) . . . . ?
C7 N1 C11 C10 1.5(15) . . . . ?
C12 N1 C11 C10 179.4(9) . . . . ?
C9 C10 C11 N1 -0.9(17) . . . . ?
C17 N2 C13 C14 1.9(15) . . . . ?
C18 N2 C13 C14 170.8(11) . . . . ?
N2 C13 C14 C15 0.1(18) . . . . ?
C13 C14 C15 C16 -5(2) . . . . ?
C14 C15 C16 C17 8(3) . . . . ?
C15 C16 C17 N2 -6(3) . . . . ?
C18 N2 C17 C16 -167.3(16) . . . . ?
C13 N2 C17 C16 1(2) . . . . ?



# 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
####################################################################### 
# 
# 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_br4q_3clpy
_database_code_depnum_ccdc_archive 'CCDC 2105672'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2017-01-24T11:42:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H14 Br2 Cl2 I2 N2 O1'
_chemical_formula_sum            'C15 H14 Br2 Cl2 I2 N2 O'
_chemical_formula_weight         722.8

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_symmetry_space_group_name_Hall  '-P 2yab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   10.9816(2)
_cell_length_b                   15.6952(2)
_cell_length_c                   13.8514(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.729(2)
_cell_angle_gamma                90
_cell_volume                     2232.86(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7680
_cell_measurement_theta_min      3.4088
_cell_measurement_theta_max      75.8055
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    2.15
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    28.571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.3367
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            11894
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         75.99
_diffrn_reflns_theta_full        75.99
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2sigma(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.
;
_reflns_number_total             4599
_reflns_number_gt                4397
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1591
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_number_reflns         4599
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1109P)²+3.4474P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.611
_refine_diff_density_min         -1.704
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
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'
Br Br -0.6763 1.2805 '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'
I I -0.3257 6.8362 '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'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.81201(4) 0.58271(3) 0.00312(4) 0.06147(18) Uani d . 1 . . I
I2 0.74390(4) 0.81841(3) 0.51248(3) 0.06232(18) Uani d . 1 . . I
Br1 0.91241(6) 0.79576(4) 0.00253(5) 0.05096(19) Uani d . 1 . . Br
Br2 0.84046(6) 0.90769(4) -0.23154(5) 0.04583(18) Uani d . 1 . . Br
O1 1.0663(6) 0.9122(3) 0.1749(4) 0.0612(12) Uani d . 1 . . O
C1 1.0337(5) 0.9527(4) 0.0941(4) 0.0430(11) Uani d . 1 . . C
C2 0.9594(5) 0.9127(4) -0.0064(5) 0.0436(11) Uani d . 1 . . C
C3 0.9287(5) 0.9560(4) -0.0943(5) 0.0433(11) Uani d . 1 . . C
Cl1 0.6100(3) 0.03181(16) 0.4009(2) 0.0981(8) Uani d . 1 . . Cl
N1 0.4294(5) 0.2408(3) 0.2722(4) 0.0501(11) Uani d . 1 . . N
C4 0.4890(7) 0.1824(4) 0.3404(6) 0.0543(14) Uani d . 1 . . C
H4 0.5023 0.1913 0.4098 0.065 Uiso calc R 1 . . H
C5 0.5319(7) 0.1086(5) 0.3105(6) 0.0609(16) Uani d . 1 . . C
C6 0.5084(9) 0.0941(5) 0.2051(7) 0.0687(19) Uani d . 1 . . C
H6 0.5354 0.0441 0.1828 0.082 Uiso calc R 1 . . H
C7 0.4458(8) 0.1549(6) 0.1381(6) 0.071(2) Uani d . 1 . . C
H7 0.4278 0.1461 0.068 0.085 Uiso calc R 1 . . H
C8 0.4082(7) 0.2282(5) 0.1691(6) 0.0595(16) Uani d . 1 . . C
H8 0.3679 0.2703 0.1211 0.071 Uiso calc R 1 . . H
C9 0.3845(9) 0.3186(5) 0.3067(8) 0.070(2) Uani d . 1 . . C
H9A 0.3429 0.3547 0.2483 0.104 Uiso calc R 1 . . H
H9B 0.4575 0.348 0.3548 0.104 Uiso calc R 1 . . H
H9C 0.3236 0.3043 0.3396 0.104 Uiso calc R 1 . . H
Cl2 0.9728(3) 0.04589(18) 0.6050(2) 0.0954(8) Uani d . 1 . . Cl
N2 1.1564(6) 0.2580(4) 0.7149(5) 0.0635(14) Uani d . 1 . . N
C10 1.0677(8) 0.2004(5) 0.6613(5) 0.0607(16) Uani d . 1 . . C
H10 0.9909 0.2187 0.6108 0.073 Uiso calc R 1 . . H
C11 1.0883(8) 0.1172(5) 0.6796(6) 0.0628(17) Uani d . 1 . . C
C12 1.1964(12) 0.0887(6) 0.7548(7) 0.081(3) Uani d . 1 . . C
H12 1.2085 0.0309 0.77 0.097 Uiso calc R 1 . . H
C13 1.2896(10) 0.1483(7) 0.8093(7) 0.082(2) Uani d . 1 . . C
H13 1.3671 0.1306 0.8593 0.098 Uiso calc R 1 . . H
C14 1.2661(9) 0.2323(7) 0.7885(7) 0.077(2) Uani d . 1 . . C
H14 1.3269 0.2724 0.8257 0.093 Uiso calc R 1 . . H
C15 1.1341(11) 0.3509(6) 0.6889(9) 0.096(3) Uani d . 1 . . C
H15A 1.0509 0.3583 0.635 0.144 Uiso calc R 1 . . H
H15B 1.2014 0.3719 0.666 0.144 Uiso calc R 1 . . H
H15C 1.1356 0.3819 0.7491 0.144 Uiso calc R 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.923(6) ?
Br2 C3 . 1.955(6) ?
O1 C1 . 1.225(8) ?
C1 C2 . 1.482(8) ?
C1 C3 3_775 1.491(8) ?
C2 C3 . 1.329(9) ?
C3 C1 3_775 1.491(8) ?
Cl1 C5 . 1.731(8) ?
N1 C4 . 1.313(9) ?
N1 C8 . 1.377(9) ?
N1 C9 . 1.459(9) ?
C4 C5 . 1.368(11) ?
C4 H4 . 0.93 ?
C5 C6 . 1.409(13) ?
C6 C7 . 1.339(13) ?
C6 H6 . 0.93 ?
C7 C8 . 1.343(13) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?
Cl2 C11 . 1.732(8) ?
N2 C14 . 1.335(11) ?
N2 C10 . 1.344(10) ?
N2 C15 . 1.502(12) ?
C10 C11 . 1.333(11) ?
C10 H10 . 0.93 ?
C11 C12 . 1.350(14) ?
C12 C13 . 1.394(16) ?
C12 H12 . 0.93 ?
C13 C14 . 1.354(15) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 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
O1 C1 C2 121.6(6) . . ?
O1 C1 C3 120.4(5) . 3_775 ?
C2 C1 C3 117.9(5) . 3_775 ?
C3 C2 C1 121.4(5) . . ?
C3 C2 Br1 124.1(5) . . ?
C1 C2 Br1 114.5(4) . . ?
C2 C3 C1 120.7(5) . 3_775 ?
C2 C3 Br2 124.7(5) . . ?
C1 C3 Br2 114.6(4) 3_775 . ?
C4 N1 C8 120.3(6) . . ?
C4 N1 C9 119.3(6) . . ?
C8 N1 C9 120.5(6) . . ?
N1 C4 C5 120.7(7) . . ?
N1 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.6(7) . . ?
C4 C5 Cl1 120.4(6) . . ?
C6 C5 Cl1 120.0(6) . . ?
C7 C6 C5 117.6(8) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C8 122.0(8) . . ?
C6 C7 H7 119 . . ?
C8 C7 H7 119 . . ?
C7 C8 N1 119.8(7) . . ?
C7 C8 H8 120.1 . . ?
N1 C8 H8 120.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 N2 C10 120.0(8) . . ?
C14 N2 C15 120.2(8) . . ?
C10 N2 C15 119.7(7) . . ?
C11 C10 N2 120.8(7) . . ?
C11 C10 H10 119.6 . . ?
N2 C10 H10 119.6 . . ?
C10 C11 C12 121.0(8) . . ?
C10 C11 Cl2 118.7(7) . . ?
C12 C11 Cl2 120.3(7) . . ?
C11 C12 C13 118.2(8) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 119.3(8) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N2 C14 C13 120.6(9) . . ?
N2 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 C3 -177.3(6) . . . . ?
C3 C1 C2 C3 1.2(8) 3_775 . . . ?
O1 C1 C2 Br1 3.0(7) . . . . ?
C3 C1 C2 Br1 -178.6(4) 3_775 . . . ?
C1 C2 C3 C1 -1.2(9) . . . 3_775 ?
Br1 C2 C3 C1 178.5(4) . . . 3_775 ?
C1 C2 C3 Br2 176.1(4) . . . . ?
Br1 C2 C3 Br2 -4.1(7) . . . . ?
C8 N1 C4 C5 0.5(10) . . . . ?
C9 N1 C4 C5 179.8(7) . . . . ?
N1 C4 C5 C6 -1.9(11) . . . . ?
N1 C4 C5 Cl1 -179.8(5) . . . . ?
C4 C5 C6 C7 1.0(12) . . . . ?
Cl1 C5 C6 C7 179.0(7) . . . . ?
C5 C6 C7 C8 1.2(13) . . . . ?
C6 C7 C8 N1 -2.6(12) . . . . ?
C4 N1 C8 C7 1.7(10) . . . . ?
C9 N1 C8 C7 -177.5(7) . . . . ?
C14 N2 C10 C11 -0.9(12) . . . . ?
C15 N2 C10 C11 176.7(9) . . . . ?
N2 C10 C11 C12 2.5(12) . . . . ?
N2 C10 C11 Cl2 -177.9(6) . . . . ?
C10 C11 C12 C13 -3.5(13) . . . . ?
Cl2 C11 C12 C13 176.8(7) . . . . ?
C11 C12 C13 C14 3.1(15) . . . . ?
C10 N2 C14 C13 0.5(14) . . . . ?
C15 N2 C14 C13 -177.1(10) . . . . ?
C12 C13 C14 N2 -1.6(15) . . . . ?



# 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
####################################################################### 
# 
# 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_br4q_3clet_1
_database_code_depnum_ccdc_archive 'CCDC 2105671'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2020-08-27T12:05:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C20 H18 Br4 Cl2 I2 N2 O2'
_chemical_formula_moiety         'C6 Br4 O2, 2(C7 H9 Cl N), 2(I)'
_chemical_formula_weight         962.7

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.5741(7)
_cell_length_b                   9.1611(7)
_cell_length_c                   9.2506(7)
_cell_angle_alpha                105.323(7)
_cell_angle_beta                 94.024(7)
_cell_angle_gamma                95.605(7)
_cell_volume                     693.94(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3315
_cell_measurement_theta_min      4.985
_cell_measurement_theta_max      75.378
_cell_measurement_temperature    293(2)
_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    26.493
_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  0.05935
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            5928
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_theta_min         4.982
_diffrn_reflns_theta_max         76.487
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2857
_reflns_number_gt                2632
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1949
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_number_reflns         2857
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1065P)²+6.0600P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.885
_refine_diff_density_min         -1.931
_refine_diff_density_rms         0.258
_refine_ls_extinction_method     none
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_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-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
I1 0.26075(8) 0.32974(7) 0.19725(8) 0.0425(3) Uani d 1 . . I
Br1 -0.38633(13) 0.31498(11) -0.09693(12) 0.0387(3) Uani d 1 . . Br
Br2 -0.13289(12) 0.16349(12) 0.10877(13) 0.0403(3) Uani d 1 . . Br
O1 -0.6832(10) 0.0923(9) -0.1951(9) 0.0439(17) Uani d 1 . . O
C1 -0.6012(12) 0.0565(10) -0.0985(11) 0.0328(19) Uani d 1 . . C
C2 -0.4413(12) 0.1349(10) -0.0391(11) 0.0327(18) Uani d 1 . . C
C3 -0.3435(11) 0.0780(10) 0.0443(11) 0.0312(18) Uani d 1 . . C
Cl1 0.5928(4) 0.2457(3) 0.4262(3) 0.0525(7) Uani d 1 . . Cl
N1 0.9727(12) 0.2712(11) 0.6981(11) 0.045(2) Uani d 1 . . N
C4 0.8591(13) 0.3055(12) 0.6079(13) 0.041(2) Uani d 1 . . C
H4 0.861293 0.403816 0.59728 0.049 Uiso calc 1 . . H
C5 0.7413(13) 0.1947(12) 0.5324(12) 0.039(2) Uani d 1 . . C
C6 0.7347(16) 0.0497(13) 0.5488(15) 0.049(3) Uani d 1 . . C
H6 0.654413 -0.025316 0.496567 0.059 Uiso calc 1 . . H
C7 0.8478(17) 0.0172(14) 0.6429(16) 0.056(3) Uani d 1 . . C
H7 0.844711 -0.080035 0.656364 0.067 Uiso calc 1 . . H
C8 0.9680(14) 0.1309(14) 0.7188(14) 0.046(3) Uani d 1 . . C
H8 1.045057 0.109796 0.783663 0.056 Uiso calc 1 . . H
C9 1.1033(15) 0.3898(15) 0.7783(16) 0.054(3) Uani d 1 . . C
H9A 1.145058 0.364795 0.867742 0.065 Uiso calc 1 . . H
H9B 1.062908 0.48739 0.80997 0.065 Uiso calc 1 . . H
C10 1.233(2) 0.4025(18) 0.6799(19) 0.069(4) Uani d 1 . . C
H10A 1.315624 0.479912 0.734896 0.104 Uiso calc 1 . . H
H10B 1.274734 0.306516 0.649786 0.104 Uiso calc 1 . . H
H10C 1.192659 0.429001 0.592065 0.104 Uiso calc 1 . . H



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.892(9) ?
Br2 C3 . 1.886(10) ?
O1 C1 . 1.230(12) ?
C1 C2 . 1.480(14) ?
C1 C3 2_455 1.497(12) ?
C2 C3 . 1.333(14) ?
Cl1 C5 . 1.728(10) ?
N1 C8 . 1.345(15) ?
N1 C4 . 1.352(14) ?
N1 C9 . 1.484(15) ?
C4 C5 . 1.366(16) ?
C4 H4 . 0.93 ?
C5 C6 . 1.373(15) ?
C6 C7 . 1.364(19) ?
C6 H6 . 0.93 ?
C7 C8 . 1.393(19) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C9 C10 . 1.50(2) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 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
O1 C1 C2 122.5(9) . . ?
O1 C1 C3 120.3(9) . 2_455 ?
C2 C1 C3 117.0(8) . 2_455 ?
C3 C2 C1 121.6(8) . . ?
C3 C2 Br1 123.5(7) . . ?
C1 C2 Br1 114.9(7) . . ?
C2 C3 C1 120.9(9) . 2_455 ?
C2 C3 Br2 123.4(7) . . ?
C1 C3 Br2 115.6(7) 2_455 . ?
C8 N1 C4 120.9(10) . . ?
C8 N1 C9 119.1(10) . . ?
C4 N1 C9 120.0(10) . . ?
N1 C4 C5 119.5(10) . . ?
N1 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.0(10) . . ?
C4 C5 Cl1 118.0(8) . . ?
C6 C5 Cl1 120.8(10) . . ?
C7 C6 C5 119.0(12) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C8 119.5(11) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
N1 C8 C7 120.0(10) . . ?
N1 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
N1 C9 C10 111.6(11) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O1 C1 C2 C3 -167.7(10) . . . . ?
C3 C1 C2 C3 7.9(16) 2_455 . . . ?
O1 C1 C2 Br1 10.1(13) . . . . ?
C3 C1 C2 Br1 -174.3(7) 2_455 . . . ?
C1 C2 C3 C1 -8.2(16) . . . 2_455 ?
Br1 C2 C3 C1 174.2(7) . . . 2_455 ?
C1 C2 C3 Br2 174.5(7) . . . . ?
Br1 C2 C3 Br2 -3.1(13) . . . . ?
C8 N1 C4 C5 -2.4(18) . . . . ?
C9 N1 C4 C5 178.7(11) . . . . ?
N1 C4 C5 C6 1.2(18) . . . . ?
N1 C4 C5 Cl1 176.6(9) . . . . ?
C4 C5 C6 C7 0.4(19) . . . . ?
Cl1 C5 C6 C7 -174.9(10) . . . . ?
C5 C6 C7 C8 -1(2) . . . . ?
C4 N1 C8 C7 2.1(19) . . . . ?
C9 N1 C8 C7 -179.0(12) . . . . ?
C6 C7 C8 N1 0(2) . . . . ?
C8 N1 C9 C10 96.9(15) . . . . ?
C4 N1 C9 C10 -84.2(15) . . . . ?



# 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
####################################################################### 
# 
# 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_s15
_database_code_depnum_ccdc_archive 'CCDC 2105668'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2017-01-30T12:06:32-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C6 Br4 O2, 2(C7 H15 N2), 2(I)'
_chemical_formula_sum            'C20 H30 Br4 I2 N4 O2'
_chemical_formula_weight         931.88

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b a m'
_symmetry_space_group_name_Hall  '-P 2 2ab'
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'
'-x, -y, -z'
'x, y, -z'
'-x-1/2, y-1/2, z'
'x-1/2, -y-1/2, z'

_cell_length_a                   13.9401(2)
_cell_length_b                   13.8771(2)
_cell_length_c                   7.60550(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1471.27(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8072
_cell_measurement_theta_min      3.1676
_cell_measurement_theta_max      75.916
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    23.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.10388
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            13009
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_theta_min         4.5
_diffrn_reflns_theta_max         76.1
_diffrn_reflns_theta_full        76.1
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2sigma(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.
;
_reflns_number_total             1651
_reflns_number_gt                1613
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.166
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_refine_ls_number_reflns         1651
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0997P)²+2.3384P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         2.7
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.176
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00080(17)
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'
Br Br -0.6763 1.2805 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.6806(5) 0.5827(5) 0 0.0553(14) Uani d S 1 . . N
C7 0.7402(4) 0.5997(4) -0.1609(9) 0.0623(13) Uani d . 1 . . C
H7A 0.7016 0.5906 -0.2656 0.075 Uiso calc R 1 . . H
H7B 0.7931 0.5543 -0.1644 0.075 Uiso calc R 1 . . H
N2 0.7442(7) 0.7547(5) 0 0.085(3) Uani d S 1 . . N
C4 0.5969(7) 0.6526(7) 0 0.075(2) Uani d S 1 . . C
H4A 0.5574 0.6432 0.1036 0.09 Uiso calc PR 0.5 . . H
H4B 0.5574 0.6432 -0.1036 0.09 Uiso calc PR 0.5 . . H
C6 0.7786(6) 0.7022(5) -0.1554(11) 0.086(2) Uani d . 1 . . C
H6A 0.8481 0.7005 -0.154 0.104 Uiso calc R 1 . . H
H6B 0.7586 0.7361 -0.2607 0.104 Uiso calc R 1 . . H
C8 0.6419(10) 0.4827(7) 0 0.078(3) Uani d S 1 . . C
H8A 0.604 0.4727 -0.1038 0.118 Uiso calc PR 0.5 . . H
H8B 0.6027 0.4732 0.1023 0.118 Uiso calc PR 0.5 . . H
H8C 0.6941 0.4375 0.0014 0.118 Uiso calc SR 1 . . H
C5 0.6411(11) 0.7551(8) 0 0.097(4) Uani d S 1 . . C
H5A 0.6187 0.7896 -0.103 0.116 Uiso calc PR 0.5 . . H
H5B 0.6187 0.7896 0.103 0.116 Uiso calc PR 0.5 . . H
Br1 0.21781(7) 0.59452(7) 0.5 0.0691(4) Uani d S 1 . . Br
Br2 0.01444(7) 0.74581(6) 0.5 0.0582(3) Uani d S 1 . . Br
O1 0.1556(5) 0.3904(4) 0.5 0.0642(14) Uani d S 1 . . O
C2 0.0141(6) 0.6038(6) 0.5 0.0549(17) Uani d S 1 . . C
C3 0.0907(6) 0.5456(5) 0.5 0.0512(15) Uani d S 1 . . C
C1 0.0837(6) 0.4424(5) 0.5 0.0552(17) Uani d S 1 . . C
I2 0 0.5 0 0.0663(3) Uani d S 1 . . I
I1 0 0 0.5 0.0676(3) Uani d S 1 . . I



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.489(11) ?
N1 C7 6 1.499(8) ?
N1 C7 . 1.499(8) ?
N1 C4 . 1.517(10) ?
C7 C6 . 1.519(9) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
N2 C5 . 1.436(17) ?
N2 C6 . 1.469(9) ?
N2 C6 6 1.469(9) ?
C4 C5 . 1.550(16) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
Br1 C3 . 1.898(8) ?
Br2 C2 . 1.971(9) ?
O1 C1 . 1.235(11) ?
C2 C3 . 1.339(13) ?
C2 C1 5_566 1.507(12) ?
C3 C1 . 1.435(11) ?
C1 C2 5_566 1.507(12) ?

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
C8 N1 C7 110.4(4) . 6 ?
C8 N1 C7 110.4(4) . . ?
C7 N1 C7 109.5(7) 6 . ?
C8 N1 C4 108.5(8) . . ?
C7 N1 C4 109.0(4) 6 . ?
C7 N1 C4 109.0(4) . . ?
N1 C7 C6 108.7(5) . . ?
N1 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N1 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C5 N2 C6 109.2(6) . . ?
C5 N2 C6 109.2(6) . 6 ?
C6 N2 C6 107.1(9) . 6 ?
N1 C4 C5 106.3(9) . . ?
N1 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
N1 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
N2 C6 C7 111.8(6) . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C5 C4 113.2(8) . . ?
N2 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
C3 C2 C1 117.7(8) . 5_566 ?
C3 C2 Br2 127.0(6) . . ?
C1 C2 Br2 115.3(6) 5_566 . ?
C2 C3 C1 123.2(7) . . ?
C2 C3 Br1 121.9(6) . . ?
C1 C3 Br1 114.9(6) . . ?
O1 C1 C3 121.9(7) . . ?
O1 C1 C2 119.0(7) . 5_566 ?
C3 C1 C2 119.1(8) . 5_566 ?

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
C8 N1 C7 C6 -179.8(7) . . . . ?
C7 N1 C7 C6 -58.0(8) 6 . . . ?
C4 N1 C7 C6 61.1(7) . . . . ?
C8 N1 C4 C5 180 . . . . ?
C7 N1 C4 C5 59.7(4) 6 . . . ?
C7 N1 C4 C5 -59.7(4) . . . . ?
C5 N2 C6 C7 -57.6(9) . . . . ?
C6 N2 C6 C7 60.5(11) 6 . . . ?
N1 C7 C6 N2 -1.8(9) . . . . ?
C6 N2 C5 C4 58.4(5) . . . . ?
C6 N2 C5 C4 -58.4(5) 6 . . . ?
N1 C4 C5 N2 0 . . . . ?
C1 C2 C3 C1 0 5_566 . . . ?
Br2 C2 C3 C1 180 . . . . ?
C1 C2 C3 Br1 180 5_566 . . . ?
Br2 C2 C3 Br1 0 . . . . ?
C2 C3 C1 O1 180 . . . . ?
Br1 C3 C1 O1 0 . . . . ?
C2 C3 C1 C2 0 . . . 5_566 ?
Br1 C3 C1 C2 180 . . . 5_566 ?



# 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
####################################################################### 
# 
# 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_n-mepybr4q-m-rt
_database_code_depnum_ccdc_archive 'CCDC 2105670'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

_audit_creation_date             2016-12-07T15:18:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_formula_sum            'C9 H8 Br2 I N O'
_chemical_formula_weight         432.88

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7730(17)
_cell_length_b                   9.519(2)
_cell_length_c                   17.246(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.254(4)
_cell_angle_gamma                90
_cell_volume                     1276.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3435
_cell_measurement_theta_min      4.6416
_cell_measurement_theta_max      77.9242
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    2.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    26.831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.36216
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54179
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            7004
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_theta_min         5.13
_diffrn_reflns_theta_max         75.14
_diffrn_reflns_theta_full        78.14
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.927
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_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 > 2sigma(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.
;
_reflns_number_total             2525
_reflns_number_gt                2305
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1761
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1248P)²+1.3662P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.815
_refine_diff_density_min         -1.214
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
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'
Br Br -0.6763 1.2805 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Br1 0.37714(10) 0.88604(10) 0.57491(5) 0.0734(3) Uani d . 1 . . Br
Br2 0.12725(11) 1.12382(11) 0.67289(5) 0.0783(3) Uani d . 1 . . Br
O1 0.1766(10) 0.8021(9) 0.4288(4) 0.097(2) Uani d . 1 . . O
C1 0.0992(10) 0.8955(9) 0.4603(5) 0.0711(19) Uani d . 1 . . C
C2 0.1592(9) 0.9572(9) 0.5357(4) 0.0681(17) Uani d . 1 . . C
C3 0.0664(9) 1.0501(9) 0.5734(4) 0.0675(16) Uani d . 1 . . C
N1 0.3411(9) 0.5467(7) 0.6854(4) 0.0741(16) Uani d . 1 . . N
C4 0.1987(17) 0.5405(13) 0.6451(10) 0.112(4) Uani d . 1 . . C
H4 0.1012 0.5873 0.6627 0.135 Uiso calc R 1 . . H
C5 0.192(3) 0.468(2) 0.5792(13) 0.158(8) Uani d . 1 . . C
H5 0.0915 0.4674 0.5501 0.19 Uiso calc R 1 . . H
C6 0.325(4) 0.397(2) 0.5551(9) 0.156(9) Uani d . 1 . . C
H6 0.3211 0.3466 0.5091 0.187 Uiso calc R 1 . . H
C7 0.476(3) 0.3996(13) 0.6002(12) 0.132(6) Uani d . 1 . . C
H7 0.5725 0.3487 0.5852 0.158 Uiso calc R 1 . . H
C8 0.4773(12) 0.4772(11) 0.6656(7) 0.092(3) Uani d . 1 . . C
H8 0.5756 0.4808 0.6962 0.111 Uiso calc R 1 . . H
C9 0.356(2) 0.6346(15) 0.7563(8) 0.121(5) Uani d . 1 . . C
H9A 0.4681 0.6223 0.7787 0.181 Uiso calc R 1 . . H
H9B 0.2699 0.6068 0.7931 0.181 Uiso calc R 1 . . H
H9C 0.3399 0.7316 0.7429 0.181 Uiso calc R 1 . . H
I1 0.21843(6) 0.22704(6) 0.35367(3) 0.0767(3) Uani d . 1 . . I



#==============================================================================

# 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.946(7) ?
Br2 C3 . 1.914(8) ?
O1 C1 . 1.203(11) ?
C1 C2 . 1.500(12) ?
C1 C3 3_576 1.504(11) ?
C2 C3 . 1.313(12) ?
C3 C1 3_576 1.504(11) ?
N1 C8 . 1.294(12) ?
N1 C4 . 1.308(16) ?
N1 C9 . 1.487(15) ?
C4 C5 . 1.33(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.30(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.40(3) ?
C6 H6 . 0.93 ?
C7 C8 . 1.35(2) ?
C7 H7 . 0.93 ?
C8 H8 . 0.93 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 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
O1 C1 C2 121.7(8) . . ?
O1 C1 C3 120.5(8) . 3_576 ?
C2 C1 C3 117.8(7) . 3_576 ?
C3 C2 C1 121.4(7) . . ?
C3 C2 Br1 122.7(6) . . ?
C1 C2 Br1 115.8(6) . . ?
C2 C3 C1 120.7(7) . 3_576 ?
C2 C3 Br2 123.7(6) . . ?
C1 C3 Br2 115.6(6) 3_576 . ?
C8 N1 C4 121.9(10) . . ?
C8 N1 C9 116.2(11) . . ?
C4 N1 C9 121.9(11) . . ?
N1 C4 C5 120.6(15) . . ?
N1 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 121(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.5(17) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 118.6(15) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N1 C8 C7 119.6(14) . . ?
N1 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C1 C2 C3 -173.7(9) . . . . ?
C3 C1 C2 C3 3.6(12) 3_576 . . . ?
O1 C1 C2 Br1 4.1(11) . . . . ?
C3 C1 C2 Br1 -178.5(5) 3_576 . . . ?
C1 C2 C3 C1 -3.8(12) . . . 3_576 ?
Br1 C2 C3 C1 178.5(5) . . . 3_576 ?
C1 C2 C3 Br2 175.7(6) . . . . ?
Br1 C2 C3 Br2 -2.1(10) . . . . ?
C8 N1 C4 C5 -3.8(19) . . . . ?
C9 N1 C4 C5 175.8(14) . . . . ?
N1 C4 C5 C6 3(3) . . . . ?
C4 C5 C6 C7 0(3) . . . . ?
C5 C6 C7 C8 -1(2) . . . . ?
C4 N1 C8 C7 2.3(15) . . . . ?
C9 N1 C8 C7 -177.3(11) . . . . ?
C6 C7 C8 N1 0.3(18) . . . . ?



# 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
