# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1408545'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2015-06-26T11:25:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H19 Br N O3'
_chemical_formula_sum            'C14 H19 Br N O3'
_chemical_formula_weight         329.21
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   23.738(2)
_cell_length_b                   5.1422(4)
_cell_length_c                   12.9446(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.153(7)
_cell_angle_gamma                90
_cell_volume                     1525.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13144
_cell_measurement_theta_min      1.63
_cell_measurement_theta_max      28.76
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  0.743
_shelx_estimated_absorpt_T_min   0.488
_shelx_estimated_absorpt_T_max   0.756

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0845
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_number            13144
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         28.758
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_coverage         0.804
_reflns_number_total             3751
_reflns_number_gt                3103
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

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

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0815P)²+13.4737P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3751
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(3)
_refine_diff_density_max         2.399
_refine_diff_density_min         -1.199
_refine_diff_density_rms         0.156

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.3309(4) 0.6186(18) 0.4335(7) 0.0216(17) Uani 1 1 d . . . . .
C2 C 0.2792(4) 0.476(2) 0.4133(7) 0.0247(17) Uani 1 1 d . . . . .
H2 H 0.2748 0.344 0.4618 0.03 Uiso 1 1 calc R U . . .
C3 C 0.2341(4) 0.526(2) 0.3232(7) 0.0260(18) Uani 1 1 d . . . . .
H3 H 0.1993 0.4266 0.3101 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2393(4) 0.722(2) 0.2514(7) 0.0257(19) Uani 1 1 d . . . . .
H4 H 0.2082 0.7564 0.19 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2907(4) 0.8657(18) 0.2710(7) 0.0247(19) Uani 1 1 d . . . . .
H5 H 0.2949 0.9998 0.2231 0.03 Uiso 1 1 calc R U . . .
C6 C 0.3354(4) 0.8124(17) 0.3600(6) 0.0211(17) Uani 1 1 d . . . . .
C7 C 0.3690(4) 0.4323(18) 0.6044(7) 0.023(2) Uani 1 1 d . . . . .
H7 H 0.3349 0.3379 0.6062 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4268(4) 0.4479(16) 0.6934(6) 0.0200(19) Uani 1 1 d . . . . .
H8 H 0.4405 0.6325 0.699 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4737(4) 0.282(2) 0.6684(7) 0.028(2) Uani 1 1 d . . . . .
H9A H 0.5093 0.2939 0.7271 0.042 Uiso 1 1 calc R U . . .
H9B H 0.4818 0.3423 0.602 0.042 Uiso 1 1 calc R U . . .
H9C H 0.4606 0.1003 0.6599 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4021(4) 0.5587(16) 0.8573(7) 0.0201(19) Uani 1 1 d . . . . .
C11 C 0.3792(4) 0.6150(18) 1.0318(7) 0.0224(18) Uani 1 1 d . . . . .
C12 C 0.4333(5) 0.768(2) 1.0811(7) 0.030(2) Uani 1 1 d . . . . .
H12A H 0.4673 0.6528 1.096 0.045 Uiso 1 1 calc R U . . .
H12B H 0.4298 0.8473 1.1481 0.045 Uiso 1 1 calc R U . . .
H12C H 0.4381 0.9054 1.0315 0.045 Uiso 1 1 calc R U . . .
C13 C 0.3661(5) 0.4209(18) 1.1087(8) 0.029(2) Uani 1 1 d . . . . .
H13A H 0.329 0.334 1.0758 0.043 Uiso 1 1 calc R U . . .
H13B H 0.3633 0.5103 1.174 0.043 Uiso 1 1 calc R U . . .
H13C H 0.3975 0.2914 1.1266 0.043 Uiso 1 1 calc R U . . .
C14 C 0.3251(4) 0.7849(19) 0.9870(7) 0.027(2) Uani 1 1 d . . . . .
H14A H 0.3344 0.9187 0.9401 0.04 Uiso 1 1 calc R U . . .
H14B H 0.3134 0.8682 1.0462 0.04 Uiso 1 1 calc R U . . .
H14C H 0.2931 0.6762 0.9461 0.04 Uiso 1 1 calc R U . . .
N1 N 0.4163(4) 0.3740(15) 0.7956(5) 0.0225(16) Uani 1 1 d . . . . .
H1 H 0.4192 0.2105 0.8164 0.027 Uiso 1 1 calc R U . . .
O1 O 0.3776(3) 0.5887(13) 0.5194(5) 0.0232(13) Uani 1 1 d . . . . .
O2 O 0.4000(3) 0.7922(12) 0.8385(5) 0.0243(14) Uani 1 1 d . . . . .
O3 O 0.3896(3) 0.4501(11) 0.9447(4) 0.0223(14) Uani 1 1 d . . . . .
Br1 Br 0.40623(4) 1.0016(2) 0.38202(6) 0.0311(3) Uani 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
C1 O1 1.358(11) . ?
C1 C2 1.394(13) . ?
C1 C6 1.401(12) . ?
C2 C3 1.385(12) . ?
C2 H2 0.95 . ?
C3 C4 1.396(14) . ?
C3 H3 0.95 . ?
C4 C5 1.393(14) . ?
C4 H4 0.95 . ?
C5 C6 1.374(13) . ?
C5 H5 0.95 . ?
C6 Br1 1.899(9) . ?
C7 O1 1.420(10) . ?
C7 C8 1.546(12) . ?
C7 H7 0.95 . ?
C8 N1 1.459(10) . ?
C8 C9 1.504(12) . ?
C8 H8 1 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O2 1.224(10) . ?
C10 N1 1.339(11) . ?
C10 O3 1.363(10) . ?
C11 O3 1.483(10) . ?
C11 C13 1.498(13) . ?
C11 C12 1.500(14) . ?
C11 C14 1.536(13) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 H1 0.88 . ?

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 125.8(8) . . ?
O1 C1 C6 116.5(8) . . ?
C2 C1 C6 117.7(8) . . ?
C3 C2 C1 120.6(10) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.8(9) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.1(8) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 119.6(9) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 122.2(9) . . ?
C5 C6 Br1 118.8(7) . . ?
C1 C6 Br1 119.0(7) . . ?
O1 C7 C8 105.6(7) . . ?
O1 C7 H7 127.2 . . ?
C8 C7 H7 127.2 . . ?
N1 C8 C9 111.0(7) . . ?
N1 C8 C7 109.5(7) . . ?
C9 C8 C7 111.9(7) . . ?
N1 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N1 125.6(8) . . ?
O2 C10 O3 124.1(8) . . ?
N1 C10 O3 110.3(7) . . ?
O3 C11 C13 103.3(7) . . ?
O3 C11 C12 109.3(8) . . ?
C13 C11 C12 111.8(8) . . ?
O3 C11 C14 109.1(7) . . ?
C13 C11 C14 109.4(8) . . ?
C12 C11 C14 113.5(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C8 119.0(7) . . ?
C10 N1 H1 120.5 . . ?
C8 N1 H1 120.5 . . ?
C1 O1 C7 116.6(7) . . ?
C10 O3 C11 120.9(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
O1 C1 C2 C3 179.2(9) . . . . ?
C6 C1 C2 C3 0.2(14) . . . . ?
C1 C2 C3 C4 -0.7(14) . . . . ?
C2 C3 C4 C5 0.5(14) . . . . ?
C3 C4 C5 C6 0.2(14) . . . . ?
C4 C5 C6 C1 -0.8(14) . . . . ?
C4 C5 C6 Br1 177.5(7) . . . . ?
O1 C1 C6 C5 -178.6(8) . . . . ?
C2 C1 C6 C5 0.6(13) . . . . ?
O1 C1 C6 Br1 3.1(11) . . . . ?
C2 C1 C6 Br1 -177.7(7) . . . . ?
O1 C7 C8 N1 160.0(7) . . . . ?
O1 C7 C8 C9 -76.5(9) . . . . ?
O2 C10 N1 C8 -4.2(13) . . . . ?
O3 C10 N1 C8 175.3(7) . . . . ?
C9 C8 N1 C10 145.5(8) . . . . ?
C7 C8 N1 C10 -90.5(9) . . . . ?
C2 C1 O1 C7 -11.6(13) . . . . ?
C6 C1 O1 C7 167.5(8) . . . . ?
C8 C7 O1 C1 -176.1(7) . . . . ?
O2 C10 O3 C11 -7.6(13) . . . . ?
N1 C10 O3 C11 173.0(7) . . . . ?
C13 C11 O3 C10 178.9(8) . . . . ?
C12 C11 O3 C10 -62.0(10) . . . . ?
C14 C11 O3 C10 62.6(10) . . . . ?


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1408546'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2015-06-26T11:00:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 Br F2 N O3'
_chemical_formula_sum            'C14 H18 Br F2 N O3'
_chemical_formula_weight         366.2
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.1112(3)
_cell_length_b                   10.0220(6)
_cell_length_c                   15.5580(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.979(2)
_cell_angle_gamma                90
_cell_volume                     792.61(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13440
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      31.25
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_T_max  0.547
_shelx_estimated_absorpt_T_min   0.478
_shelx_estimated_absorpt_T_max   0.584

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_number            13440
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         31.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.844
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.844
_reflns_Friedel_coverage         0.903
_reflns_number_total             3440
_reflns_number_gt                3147
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

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

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0091P)²+0.8889P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.038(11)
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
C1 C 0.3168(6) 0.7447(4) 0.67972(19) 0.0252(7) Uani 1 1 d . . . . .
C2 C 0.4704(8) 0.8050(4) 0.6222(2) 0.0260(8) Uani 1 1 d . . . . .
C3 C 0.5018(8) 0.9408(4) 0.6200(3) 0.0305(8) Uani 1 1 d . . . . .
C4 C 0.3811(10) 1.0216(4) 0.6745(3) 0.0381(10) Uani 1 1 d . . . . .
H4 H 0.4062 1.1155 0.6732 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2227(9) 0.9663(5) 0.7314(3) 0.0381(10) Uani 1 1 d . . . . .
H5 H 0.1343 1.0219 0.7685 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1925(8) 0.8279(5) 0.7343(2) 0.0330(9) Uani 1 1 d . . . . .
C7 C 0.1047(7) 0.5455(4) 0.6279(2) 0.0243(7) Uani 1 1 d . . . . .
H7A H 0.1061 0.5785 0.568 0.029 Uiso 1 1 calc R U . . .
H7B H -0.0691 0.5655 0.6475 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1566(6) 0.3968(3) 0.6316(2) 0.0194(7) Uani 1 1 d . . . . .
H8 H 0.3341 0.3799 0.6122 0.023 Uiso 1 1 calc R U . . .
C9 C -0.0474(7) 0.3227(4) 0.5713(2) 0.0264(8) Uani 1 1 d . . . . .
H9A H -0.2231 0.3396 0.5887 0.04 Uiso 1 1 calc R U . . .
H9B H -0.0106 0.2267 0.5743 0.04 Uiso 1 1 calc R U . . .
H9C H -0.0397 0.354 0.5119 0.04 Uiso 1 1 calc R U . . .
C10 C 0.3823(6) 0.3370(3) 0.7730(2) 0.0170(6) Uani 1 1 d . . . . .
C11 C 0.5396(7) 0.3013(3) 0.9250(2) 0.0206(7) Uani 1 1 d . . . . .
C12 C 0.7126(7) 0.4264(4) 0.9318(2) 0.0260(8) Uani 1 1 d . . . . .
H12A H 0.6011 0.506 0.9247 0.039 Uiso 1 1 calc R U . . .
H12B H 0.832 0.4245 0.8864 0.039 Uiso 1 1 calc R U . . .
H12C H 0.8156 0.4287 0.9885 0.039 Uiso 1 1 calc R U . . .
C13 C 0.3881(7) 0.2917(4) 1.0044(2) 0.0295(9) Uani 1 1 d . . . . .
H13A H 0.2698 0.2146 0.9984 0.044 Uiso 1 1 calc R U . . .
H13B H 0.2848 0.3733 1.0093 0.044 Uiso 1 1 calc R U . . .
H13C H 0.5124 0.2812 1.0563 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6898(8) 0.1734(4) 0.9136(3) 0.0269(8) Uani 1 1 d . . . . .
H14A H 0.7973 0.1835 0.8655 0.04 Uiso 1 1 calc R U . . .
H14B H 0.5652 0.0998 0.9014 0.04 Uiso 1 1 calc R U . . .
H14C H 0.8039 0.154 0.9668 0.04 Uiso 1 1 calc R U . . .
N1 N 0.1572(5) 0.3487(3) 0.71994(17) 0.0169(5) Uani 1 1 d . . . . .
H1 H 0.0071 0.3267 0.7392 0.02 Uiso 1 1 calc R U . . .
O1 O 0.3117(6) 0.6090(3) 0.68420(18) 0.0334(7) Uani 1 1 d . . . . .
O2 O 0.6032(5) 0.3401(3) 0.75022(15) 0.0232(5) Uani 1 1 d . . . . .
O3 O 0.3252(5) 0.3170(2) 0.85474(15) 0.0206(5) Uani 1 1 d . . . . .
F1 F 0.5912(4) 0.7285(3) 0.56736(14) 0.0370(6) Uani 1 1 d . . . . .
F2 F 0.6556(6) 0.9926(3) 0.56279(17) 0.0450(7) Uani 1 1 d . . . . .
Br1 Br -0.01937(9) 0.75043(8) 0.81271(2) 0.05875(19) Uani 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
C1 O1 1.362(5) . ?
C1 C2 1.388(5) . ?
C1 C6 1.390(5) . ?
C2 F1 1.344(4) . ?
C2 C3 1.371(5) . ?
C3 F2 1.351(5) . ?
C3 C4 1.366(6) . ?
C4 C5 1.376(7) . ?
C4 H4 0.95 . ?
C5 C6 1.396(7) . ?
C5 H5 0.95 . ?
C6 Br1 1.882(4) . ?
C7 O1 1.449(4) . ?
C7 C8 1.514(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N1 1.456(4) . ?
C8 C9 1.522(5) . ?
C8 H8 1 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O2 1.219(4) . ?
C10 O3 1.348(4) . ?
C10 N1 1.350(4) . ?
C11 O3 1.474(4) . ?
C11 C14 1.515(5) . ?
C11 C13 1.527(5) . ?
C11 C12 1.531(5) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 H1 0.88 . ?

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 118.8(3) . . ?
O1 C1 C6 123.7(3) . . ?
C2 C1 C6 117.2(4) . . ?
F1 C2 C3 119.2(4) . . ?
F1 C2 C1 119.3(3) . . ?
C3 C2 C1 121.5(4) . . ?
F2 C3 C4 120.9(4) . . ?
F2 C3 C2 118.4(4) . . ?
C4 C3 C2 120.8(4) . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 121.1(4) . . ?
C1 C6 Br1 118.6(3) . . ?
C5 C6 Br1 120.2(3) . . ?
O1 C7 C8 107.2(3) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
N1 C8 C7 110.2(3) . . ?
N1 C8 C9 110.8(3) . . ?
C7 C8 C9 110.5(3) . . ?
N1 C8 H8 108.4 . . ?
C7 C8 H8 108.4 . . ?
C9 C8 H8 108.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O3 125.2(3) . . ?
O2 C10 N1 125.2(3) . . ?
O3 C10 N1 109.6(3) . . ?
O3 C11 C14 110.5(3) . . ?
O3 C11 C13 101.9(3) . . ?
C14 C11 C13 110.3(3) . . ?
O3 C11 C12 110.1(3) . . ?
C14 C11 C12 113.9(3) . . ?
C13 C11 C12 109.5(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C8 121.6(3) . . ?
C10 N1 H1 119.2 . . ?
C8 N1 H1 119.2 . . ?
C1 O1 C7 115.1(3) . . ?
C10 O3 C11 119.9(3) . . ?

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 F1 5.7(5) . . . . ?
C6 C1 C2 F1 -179.0(3) . . . . ?
O1 C1 C2 C3 -174.2(3) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
F1 C2 C3 F2 -0.4(6) . . . . ?
C1 C2 C3 F2 179.5(3) . . . . ?
F1 C2 C3 C4 179.7(4) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
F2 C3 C4 C5 179.1(4) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
O1 C1 C6 C5 174.6(4) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
O1 C1 C6 Br1 -5.4(5) . . . . ?
C2 C1 C6 Br1 179.6(3) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C4 C5 C6 Br1 179.1(3) . . . . ?
O1 C7 C8 N1 59.4(4) . . . . ?
O1 C7 C8 C9 -177.8(3) . . . . ?
O2 C10 N1 C8 -14.3(5) . . . . ?
O3 C10 N1 C8 167.6(3) . . . . ?
C7 C8 N1 C10 -94.5(4) . . . . ?
C9 C8 N1 C10 142.9(3) . . . . ?
C2 C1 O1 C7 -91.6(4) . . . . ?
C6 C1 O1 C7 93.5(4) . . . . ?
C8 C7 O1 C1 171.4(3) . . . . ?
O2 C10 O3 C11 2.0(5) . . . . ?
N1 C10 O3 C11 -179.9(3) . . . . ?
C14 C11 O3 C10 -66.7(4) . . . . ?
C13 C11 O3 C10 176.1(3) . . . . ?
C12 C11 O3 C10 59.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 2.09 2.920(3) 156 1_455


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1408549'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2015-06-26T11:44:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H20 I N O3'
_chemical_formula_sum            'C14 H20 I N O3'
_chemical_formula_weight         377.21
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.11230(10)
_cell_length_b                   13.3078(3)
_cell_length_c                   22.6516(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1541.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    32273
_cell_measurement_theta_min      1.78
_cell_measurement_theta_max      28.66
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.626
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  0.795
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.803

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

_diffrn_source                   'fine-focus sealed tube'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_number            32273
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.775
_diffrn_reflns_theta_max         28.656
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.717
_reflns_number_total             3919
_reflns_number_gt                3845
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

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

_atom_sites_solution_primary     'iterative - e.g. charge flipping method'
_atom_sites_solution_secondary   'iterative - e.g. charge flipping method'
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0162P)²+5.5364P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_diff_density_max         0.966
_refine_diff_density_min         -1.085
_refine_diff_density_rms         0.087

#----------------------------------------------------------------------------#
#                   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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C1 C 0.3853(8) 0.8529(3) 0.90882(18) 0.0160(8) Uani 1 1 d . . . . .
C2 C 0.2668(10) 0.8460(3) 0.96447(16) 0.0201(8) Uani 1 1 d . . . . .
H2 H 0.1442 0.794 0.9723 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3295(9) 0.9154(3) 1.00814(19) 0.0218(9) Uani 1 1 d . . . . .
H3 H 0.2441 0.9119 1.0453 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5140(10) 0.9895(3) 0.9983(2) 0.0214(9) Uani 1 1 d . . . . .
H4 H 0.5604 1.0347 1.029 0.026 Uiso 1 1 calc R U . . .
C5 C 0.6312(9) 0.9970(3) 0.94301(19) 0.0200(8) Uani 1 1 d . . . . .
H5 H 0.7576 1.0479 0.9359 0.024 Uiso 1 1 calc R U . . .
C6 C 0.5648(8) 0.9308(3) 0.89842(19) 0.0172(8) Uani 1 1 d . . . . .
C7 C 0.1961(10) 0.6974(3) 0.87771(17) 0.0169(8) Uani 1 1 d . . . . .
H7A H 0.0192 0.7139 0.8927 0.02 Uiso 1 1 calc R U . . .
H7B H 0.2905 0.6591 0.9085 0.02 Uiso 1 1 calc R U . . .
C8 C 0.1767(7) 0.6357(3) 0.82110(17) 0.0140(7) Uani 1 1 d . . . . .
H8 H 0.3495 0.6381 0.8004 0.017 Uiso 1 1 calc R U . . .
C9 C -0.0319(9) 0.6766(3) 0.77974(19) 0.0170(8) Uani 1 1 d . . . . .
H9A H -0.2017 0.6762 0.7998 0.026 Uiso 1 1 calc R U . . .
H9B H -0.0412 0.6344 0.7443 0.026 Uiso 1 1 calc R U . . .
H9C H 0.0128 0.7456 0.7684 0.026 Uiso 1 1 calc R U . . .
C10 C 0.3118(7) 0.4688(3) 0.85313(16) 0.0130(7) Uani 1 1 d . . . . .
C11 C 0.3879(8) 0.2931(3) 0.88062(18) 0.0130(7) Uani 1 1 d . . . . .
C12 C 0.5451(9) 0.3147(3) 0.93613(19) 0.0191(8) Uani 1 1 d . . . . .
H12A H 0.428 0.3394 0.9672 0.029 Uiso 1 1 calc R U . . .
H12B H 0.678 0.3657 0.9275 0.029 Uiso 1 1 calc R U . . .
H12C H 0.6309 0.2529 0.9495 0.029 Uiso 1 1 calc R U . . .
C13 C 0.5575(8) 0.2710(3) 0.82703(18) 0.0178(8) Uani 1 1 d . . . . .
H13A H 0.6977 0.321 0.8245 0.027 Uiso 1 1 calc R U . . .
H13B H 0.4501 0.274 0.7912 0.027 Uiso 1 1 calc R U . . .
H13C H 0.6339 0.2038 0.8308 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1979(9) 0.2065(3) 0.89144(19) 0.0195(8) Uani 1 1 d . . . . .
H14A H 0.0974 0.1935 0.8554 0.029 Uiso 1 1 calc R U . . .
H14B H 0.078 0.2244 0.9235 0.029 Uiso 1 1 calc R U . . .
H14C H 0.2962 0.1461 0.9023 0.029 Uiso 1 1 calc R U . . .
N1 N 0.1181(6) 0.5312(2) 0.83619(15) 0.0135(6) Uani 1 1 d . . . . .
H1 H -0.0439 0.5091 0.8342 0.016 Uiso 1 1 calc R U . . .
O1 O 0.3367(6) 0.7882(2) 0.86340(13) 0.0187(6) Uani 1 1 d . . . . .
O2 O 0.5423(6) 0.4918(2) 0.85513(14) 0.0162(6) Uani 1 1 d . . . . .
O3 O 0.2113(6) 0.37786(18) 0.86726(12) 0.0130(5) Uani 1 1 d . . . . .
I1 I 0.72410(6) 0.95059(2) 0.81416(2) 0.02463(8) Uani 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
C1 O1 1.364(5) . ?
C1 C2 1.402(6) . ?
C1 C6 1.404(6) . ?
C2 C3 1.391(6) . ?
C2 H2 0.95 . ?
C3 C4 1.382(7) . ?
C3 H3 0.95 . ?
C4 C5 1.393(7) . ?
C4 H4 0.95 . ?
C5 C6 1.382(6) . ?
C5 H5 0.95 . ?
C6 I1 2.092(4) . ?
C7 O1 1.443(5) . ?
C7 C8 1.526(5) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N1 1.463(5) . ?
C8 C9 1.520(5) . ?
C8 H8 1 . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 O2 1.219(5) . ?
C10 N1 1.349(5) . ?
C10 O3 1.353(4) . ?
C11 O3 1.476(4) . ?
C11 C13 1.521(6) . ?
C11 C12 1.520(6) . ?
C11 C14 1.527(6) . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
N1 H1 0.88 . ?

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 123.9(4) . . ?
O1 C1 C6 117.3(4) . . ?
C2 C1 C6 118.8(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.5(4) . . ?
C5 C6 I1 119.4(3) . . ?
C1 C6 I1 120.0(3) . . ?
O1 C7 C8 107.1(3) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
N1 C8 C9 109.9(3) . . ?
N1 C8 C7 109.2(3) . . ?
C9 C8 C7 111.8(3) . . ?
N1 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
C7 C8 H8 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 N1 124.5(4) . . ?
O2 C10 O3 125.7(3) . . ?
N1 C10 O3 109.9(3) . . ?
O3 C11 C13 109.4(3) . . ?
O3 C11 C12 110.4(3) . . ?
C13 C11 C12 113.3(3) . . ?
O3 C11 C14 102.7(3) . . ?
C13 C11 C14 110.2(3) . . ?
C12 C11 C14 110.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 N1 C8 120.1(3) . . ?
C10 N1 H1 119.9 . . ?
C8 N1 H1 119.9 . . ?
C1 O1 C7 116.7(3) . . ?
C10 O3 C11 120.0(3) . . ?

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 179.8(4) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C1 C2 C3 C4 -2.3(7) . . . . ?
C2 C3 C4 C5 2.6(7) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
C4 C5 C6 C1 -2.2(7) . . . . ?
C4 C5 C6 I1 175.6(3) . . . . ?
O1 C1 C6 C5 -177.6(4) . . . . ?
C2 C1 C6 C5 2.5(6) . . . . ?
O1 C1 C6 I1 4.6(5) . . . . ?
C2 C1 C6 I1 -175.3(3) . . . . ?
O1 C7 C8 N1 161.1(3) . . . . ?
O1 C7 C8 C9 -77.1(4) . . . . ?
O2 C10 N1 C8 -2.7(6) . . . . ?
O3 C10 N1 C8 177.4(3) . . . . ?
C9 C8 N1 C10 155.5(3) . . . . ?
C7 C8 N1 C10 -81.6(4) . . . . ?
C2 C1 O1 C7 -12.5(6) . . . . ?
C6 C1 O1 C7 167.6(4) . . . . ?
C8 C7 O1 C1 -177.5(3) . . . . ?
O2 C10 O3 C11 -6.9(5) . . . . ?
N1 C10 O3 C11 173.0(3) . . . . ?
C13 C11 O3 C10 -60.8(4) . . . . ?
C12 C11 O3 C10 64.6(4) . . . . ?
C14 C11 O3 C10 -177.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B O2 0.98 2.45 2.987(5) 114 .
C13 H13A O2 0.98 2.51 3.007(5) 112 .
C12 H12B O2 0.98 2.45 2.987(5) 114 .
C13 H13A O2 0.98 2.51 3.007(5) 112 .


# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1419382'
_audit_update_record             
;
2015-08-17 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Br F N O3'
_chemical_formula_sum            'C13 H15 Br F N O3'
_chemical_formula_weight         332.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0120(2)
_cell_length_b                   12.0546(3)
_cell_length_c                   14.3104(4)
_cell_angle_alpha                75.3280(10)
_cell_angle_beta                 89.1280(10)
_cell_angle_gamma                89.8310(10)
_cell_volume                     1336.90(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      28.42

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.090
_shelx_estimated_absorpt_T_min   0.457
_shelx_estimated_absorpt_T_max   0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_T_max  0.671
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'


_exptl_special_details           
;
School of Chemsitry and Physics
University of KwaZulu-Natal
Private Bag X 54001
Durban
4000
;


_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23444
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.471
_diffrn_reflns_theta_max         25.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4955
_reflns_number_gt                4636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_special_details          
;
School of Chemsitry and Physics
University of KwaZulu-Natal
Private Bag X 54001
Durban
4000
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+5.1240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4955
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.6498(4) 0.9894(3) 0.3051(3) 0.0161(7) Uani 1 1 d . . . . .
C2 C 0.5753(5) 1.0874(3) 0.3203(3) 0.0193(8) Uani 1 1 d . . . . .
H2 H 0.5526 1.0935 0.3842 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5339(5) 1.1768(3) 0.2415(3) 0.0235(9) Uani 1 1 d . . . . .
H3 H 0.4829 1.2446 0.2508 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5678(5) 1.1656(3) 0.1507(3) 0.0204(8) Uani 1 1 d . . . . .
C5 C 0.6457(4) 1.0691(3) 0.1329(3) 0.0162(7) Uani 1 1 d . . . . .
C6 C 0.6898(4) 0.9794(3) 0.2123(3) 0.0134(7) Uani 1 1 d . . . . .
C7 C 0.7332(5) 0.9643(3) 0.0194(3) 0.0192(8) Uani 1 1 d . . . . .
H7A H 0.8562 0.9696 0.0127 0.023 Uiso 1 1 calc R U . . .
H7B H 0.6881 0.9554 -0.0423 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6863(4) 0.8610(3) 0.0995(2) 0.0151(7) Uani 1 1 d . . . . .
H8A H 0.5634 0.8526 0.1048 0.018 Uiso 1 1 calc R U . . .
H8B H 0.7340 0.7906 0.0861 0.018 Uiso 1 1 calc R U . . .
C9 C 0.9150(4) 0.8385(3) 0.2109(3) 0.0147(7) Uani 1 1 d . . . . .
C10 C 1.1474(4) 0.8391(3) 0.3182(3) 0.0141(7) Uani 1 1 d . . . . .
C11 C 1.1374(5) 0.7098(3) 0.3597(3) 0.0204(8) Uani 1 1 d . . . . .
H11A H 1.2454 0.6812 0.3870 0.031 Uiso 1 1 calc R U . . .
H11B H 1.0511 0.6921 0.4106 0.031 Uiso 1 1 calc R U . . .
H11C H 1.1092 0.6729 0.3083 0.031 Uiso 1 1 calc R U . . .
C12 C 1.2837(5) 0.8727(3) 0.2416(3) 0.0195(8) Uani 1 1 d . . . . .
H12A H 1.3909 0.8422 0.2689 0.029 Uiso 1 1 calc R U . . .
H12B H 1.2580 0.8411 0.1867 0.029 Uiso 1 1 calc R U . . .
H12C H 1.2904 0.9564 0.2197 0.029 Uiso 1 1 calc R U . . .
C13 C 1.1708(5) 0.8993(3) 0.3983(3) 0.0193(8) Uani 1 1 d . . . . .
H13A H 1.2758 0.8741 0.4313 0.029 Uiso 1 1 calc R U . . .
H13B H 1.1741 0.9824 0.3706 0.029 Uiso 1 1 calc R U . . .
H13C H 1.0776 0.8801 0.4447 0.029 Uiso 1 1 calc R U . . .
C14 C 0.1540(4) 0.3362(3) 0.2971(3) 0.0153(7) Uani 1 1 d . . . . .
C15 C 0.0850(5) 0.2283(3) 0.3116(3) 0.0196(8) Uani 1 1 d . . . . .
H15 H 0.0630 0.1831 0.3753 0.023 Uiso 1 1 calc R U . . .
C16 C 0.0480(5) 0.1860(3) 0.2325(3) 0.0215(8) Uani 1 1 d . . . . .
H16 H 0.0007 0.1119 0.2411 0.026 Uiso 1 1 calc R U . . .
C17 C 0.0812(5) 0.2535(3) 0.1418(3) 0.0187(8) Uani 1 1 d . . . . .
C18 C 0.1533(4) 0.3617(3) 0.1251(3) 0.0148(7) Uani 1 1 d . . . . .
C19 C 0.1940(4) 0.4041(3) 0.2046(2) 0.0133(7) Uani 1 1 d . . . . .
C20 C 0.1868(5) 0.5902(3) 0.0945(2) 0.0154(7) Uani 1 1 d . . . . .
H20A H 0.2324 0.6689 0.0819 0.018 Uiso 1 1 calc R U . . .
H20B H 0.0637 0.5944 0.0993 0.018 Uiso 1 1 calc R U . . .
C21 C 0.2362(5) 0.5370(3) 0.0141(3) 0.0174(7) Uani 1 1 d . . . . .
H21A H 0.1909 0.5836 -0.0474 0.021 Uiso 1 1 calc R U . . .
H21B H 0.3594 0.5370 0.0077 0.021 Uiso 1 1 calc R U . . .
C22 C 0.4136(4) 0.5469(3) 0.2085(3) 0.0145(7) Uani 1 1 d . . . . .
C23 C 0.6482(4) 0.4780(3) 0.3137(2) 0.0141(7) Uani 1 1 d . . . . .
C24 C 0.6775(5) 0.3659(3) 0.3873(3) 0.0229(8) Uani 1 1 d . . . . .
H24A H 0.7820 0.3703 0.4209 0.034 Uiso 1 1 calc R U . . .
H24B H 0.5847 0.3508 0.4342 0.034 Uiso 1 1 calc R U . . .
H24C H 0.6848 0.3037 0.3546 0.034 Uiso 1 1 calc R U . . .
C25 C 0.7851(5) 0.5004(4) 0.2366(3) 0.0224(8) Uani 1 1 d . . . . .
H25A H 0.8911 0.5134 0.2654 0.034 Uiso 1 1 calc R U . . .
H25B H 0.7957 0.4340 0.2092 0.034 Uiso 1 1 calc R U . . .
H25C H 0.7567 0.5684 0.1853 0.034 Uiso 1 1 calc R U . . .
C26 C 0.6305(5) 0.5758(4) 0.3626(3) 0.0240(8) Uani 1 1 d . . . . .
H26A H 0.7370 0.5878 0.3914 0.036 Uiso 1 1 calc R U . . .
H26B H 0.5993 0.6461 0.3146 0.036 Uiso 1 1 calc R U . . .
H26C H 0.5439 0.5567 0.4132 0.036 Uiso 1 1 calc R U . . .
N1 N 0.7536(4) 0.8783(2) 0.1903(2) 0.0140(6) Uani 1 1 d . . . . .
N2 N 0.2541(4) 0.5184(2) 0.1850(2) 0.0140(6) Uani 1 1 d . . . . .
O1 O 0.6685(3) 1.0684(2) 0.03870(18) 0.0200(6) Uani 1 1 d . . . . .
O2 O 0.9853(3) 0.8857(2) 0.27605(18) 0.0150(5) Uani 1 1 d . . . . .
O3 O 0.9788(3) 0.7692(2) 0.1736(2) 0.0226(6) Uani 1 1 d . . . . .
O4 O 0.1750(3) 0.4208(2) 0.03148(18) 0.0190(5) Uani 1 1 d . . . . .
O5 O 0.4878(3) 0.4584(2) 0.26945(18) 0.0147(5) Uani 1 1 d . . . . .
O6 O 0.4724(3) 0.6408(2) 0.1766(2) 0.0224(6) Uani 1 1 d . . . . .
F1 F 0.5237(3) 1.25103(19) 0.07239(17) 0.0276(5) Uani 1 1 d . . . . .
F2 F 0.0405(3) 0.21284(19) 0.06346(16) 0.0238(5) Uani 1 1 d . . . . .
Br1 Br 0.67995(4) 0.86433(3) 0.41441(3) 0.01811(11) Uani 1 1 d . . . . .
Br2 Br 0.18189(5) 0.39437(3) 0.40687(2) 0.01848(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.385(5) . ?
C1 C6 1.397(5) . ?
C1 Br1 1.895(4) . ?
C2 C3 1.393(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.362(6) . ?
C3 H3 0.9500 . ?
C4 F1 1.366(4) . ?
C4 C5 1.396(5) . ?
C5 O1 1.360(5) . ?
C5 C6 1.404(5) . ?
C6 N1 1.425(4) . ?
C7 O1 1.445(5) . ?
C7 C8 1.508(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.477(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O3 1.209(4) . ?
C9 O2 1.340(4) . ?
C9 N1 1.387(5) . ?
C10 O2 1.487(4) . ?
C10 C12 1.517(5) . ?
C10 C13 1.518(5) . ?
C10 C11 1.522(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.380(5) . ?
C14 C19 1.402(5) . ?
C14 Br2 1.892(4) . ?
C15 C16 1.390(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(6) . ?
C16 H16 0.9500 . ?
C17 F2 1.376(4) . ?
C17 C18 1.390(5) . ?
C18 O4 1.358(4) . ?
C18 C19 1.403(5) . ?
C19 N2 1.419(5) . ?
C20 N2 1.472(4) . ?
C20 C21 1.499(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O4 1.446(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O6 1.203(4) . ?
C22 O5 1.339(4) . ?
C22 N2 1.392(5) . ?
C23 O5 1.487(4) . ?
C23 C24 1.508(5) . ?
C23 C25 1.519(5) . ?
C23 C26 1.521(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(3) . . ?
C2 C1 Br1 117.5(3) . . ?
C6 C1 Br1 120.8(3) . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 F1 119.7(3) . . ?
C3 C4 C5 123.0(3) . . ?
F1 C4 C5 117.3(4) . . ?
O1 C5 C4 116.6(3) . . ?
O1 C5 C6 125.0(3) . . ?
C4 C5 C6 118.3(3) . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 N1 124.7(3) . . ?
C5 C6 N1 116.2(3) . . ?
O1 C7 C8 111.1(3) . . ?
O1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C7 107.7(3) . . ?
N1 C8 H8A 110.2 . . ?
C7 C8 H8A 110.2 . . ?
N1 C8 H8B 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
O3 C9 O2 126.2(3) . . ?
O3 C9 N1 122.2(3) . . ?
O2 C9 N1 111.6(3) . . ?
O2 C10 C12 109.0(3) . . ?
O2 C10 C13 102.8(3) . . ?
C12 C10 C13 110.9(3) . . ?
O2 C10 C11 111.1(3) . . ?
C12 C10 C11 112.1(3) . . ?
C13 C10 C11 110.5(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 122.1(3) . . ?
C15 C14 Br2 117.5(3) . . ?
C19 C14 Br2 120.3(3) . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 F2 118.6(3) . . ?
C16 C17 C18 123.0(3) . . ?
F2 C17 C18 118.4(3) . . ?
O4 C18 C17 116.9(3) . . ?
O4 C18 C19 124.3(3) . . ?
C17 C18 C19 118.8(3) . . ?
C14 C19 C18 117.8(3) . . ?
C14 C19 N2 124.4(3) . . ?
C18 C19 N2 117.3(3) . . ?
N2 C20 C21 108.0(3) . . ?
N2 C20 H20A 110.1 . . ?
C21 C20 H20A 110.1 . . ?
N2 C20 H20B 110.1 . . ?
C21 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
O4 C21 C20 111.5(3) . . ?
O4 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
O4 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
O6 C22 O5 126.2(3) . . ?
O6 C22 N2 122.2(3) . . ?
O5 C22 N2 111.7(3) . . ?
O5 C23 C24 103.2(3) . . ?
O5 C23 C25 109.2(3) . . ?
C24 C23 C25 110.7(3) . . ?
O5 C23 C26 110.4(3) . . ?
C24 C23 C26 110.8(3) . . ?
C25 C23 C26 112.2(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C9 N1 C6 123.5(3) . . ?
C9 N1 C8 115.0(3) . . ?
C6 N1 C8 112.3(3) . . ?
C22 N2 C19 123.5(3) . . ?
C22 N2 C20 115.8(3) . . ?
C19 N2 C20 111.7(3) . . ?
C5 O1 C7 117.1(3) . . ?
C9 O2 C10 118.5(3) . . ?
C18 O4 C21 116.9(3) . . ?
C22 O5 C23 119.0(3) . . ?

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
C6 C1 C2 C3 2.1(6) . . . . ?
Br1 C1 C2 C3 -173.1(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 F1 178.1(3) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 O1 178.6(3) . . . . ?
F1 C4 C5 O1 -0.9(5) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
F1 C4 C5 C6 -179.0(3) . . . . ?
C2 C1 C6 C5 -3.0(5) . . . . ?
Br1 C1 C6 C5 172.0(3) . . . . ?
C2 C1 C6 N1 -174.6(3) . . . . ?
Br1 C1 C6 N1 0.5(5) . . . . ?
O1 C5 C6 C1 -176.2(3) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
O1 C5 C6 N1 -4.0(5) . . . . ?
C4 C5 C6 N1 173.9(3) . . . . ?
O1 C7 C8 N1 -58.3(4) . . . . ?
C19 C14 C15 C16 -2.3(6) . . . . ?
Br2 C14 C15 C16 174.2(3) . . . . ?
C14 C15 C16 C17 -0.1(6) . . . . ?
C15 C16 C17 F2 -178.3(3) . . . . ?
C15 C16 C17 C18 1.3(6) . . . . ?
C16 C17 C18 O4 -178.2(3) . . . . ?
F2 C17 C18 O4 1.4(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
F2 C17 C18 C19 179.5(3) . . . . ?
C15 C14 C19 C18 3.4(5) . . . . ?
Br2 C14 C19 C18 -173.0(2) . . . . ?
C15 C14 C19 N2 175.4(3) . . . . ?
Br2 C14 C19 N2 -0.9(5) . . . . ?
O4 C18 C19 C14 175.8(3) . . . . ?
C17 C18 C19 C14 -2.2(5) . . . . ?
O4 C18 C19 N2 3.2(5) . . . . ?
C17 C18 C19 N2 -174.8(3) . . . . ?
N2 C20 C21 O4 58.3(4) . . . . ?
O3 C9 N1 C6 -163.1(3) . . . . ?
O2 C9 N1 C6 17.4(5) . . . . ?
O3 C9 N1 C8 -19.0(5) . . . . ?
O2 C9 N1 C8 161.5(3) . . . . ?
C1 C6 N1 C9 -72.4(5) . . . . ?
C5 C6 N1 C9 115.9(4) . . . . ?
C1 C6 N1 C8 142.7(3) . . . . ?
C5 C6 N1 C8 -29.1(4) . . . . ?
C7 C8 N1 C9 -88.9(4) . . . . ?
C7 C8 N1 C6 59.2(4) . . . . ?
O6 C22 N2 C19 166.6(3) . . . . ?
O5 C22 N2 C19 -13.8(5) . . . . ?
O6 C22 N2 C20 22.2(5) . . . . ?
O5 C22 N2 C20 -158.2(3) . . . . ?
C14 C19 N2 C22 71.3(5) . . . . ?
C18 C19 N2 C22 -116.6(4) . . . . ?
C14 C19 N2 C20 -143.0(3) . . . . ?
C18 C19 N2 C20 29.0(4) . . . . ?
C21 C20 N2 C22 89.9(4) . . . . ?
C21 C20 N2 C19 -58.6(4) . . . . ?
C4 C5 O1 C7 -173.8(3) . . . . ?
C6 C5 O1 C7 4.2(5) . . . . ?
C8 C7 O1 C5 27.7(4) . . . . ?
O3 C9 O2 C10 -9.1(5) . . . . ?
N1 C9 O2 C10 170.3(3) . . . . ?
C12 C10 O2 C9 71.2(4) . . . . ?
C13 C10 O2 C9 -171.1(3) . . . . ?
C11 C10 O2 C9 -52.9(4) . . . . ?
C17 C18 O4 C21 174.7(3) . . . . ?
C19 C18 O4 C21 -3.3(5) . . . . ?
C20 C21 O4 C18 -28.1(4) . . . . ?
O6 C22 O5 C23 8.6(5) . . . . ?
N2 C22 O5 C23 -171.0(3) . . . . ?
C24 C23 O5 C22 171.8(3) . . . . ?
C25 C23 O5 C22 -70.4(4) . . . . ?
C26 C23 O5 C22 53.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O6 0.99 2.60 3.111(4) 112 .
C11 H11C O3 0.98 2.25 2.890(5) 121 .
C26 H26B O6 0.98 2.25 2.889(5) 121 .
C12 H12B O3 0.98 2.43 3.029(5) 119 .
C25 H25C O6 0.98 2.43 3.030(5) 119 .

_refine_diff_density_max         2.237
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.101

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
