# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_140708a
_database_code_depnum_ccdc_archive 'CCDC 1440589'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Br2 F N2 O2'
_chemical_formula_weight         576.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.25(4)
_cell_length_b                   18.52(3)
_cell_length_c                   15.75(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.715(14)
_cell_angle_gamma                90.00
_cell_volume                     5062(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2428
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      23.78

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          2.40
_exptl_crystal_size_mid          2.00
_exptl_crystal_size_min          1.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2320
_exptl_absorpt_coefficient_mu    3.235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0478
_exptl_absorpt_correction_T_max  0.0852
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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            12751
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.04
_reflns_number_total             4470
_reflns_number_gt                2515
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1228P)²+23.3661P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     301
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.2467
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.05784(7) 0.79099(4) 0.91057(9) 0.0932(5) Uani 1 1 d . . .
Br2 Br -0.05121(7) -0.03705(5) 0.80543(11) 0.1008(5) Uani 1 1 d . . .
C1 C -0.0478(5) 0.0658(4) 0.8087(8) 0.065(2) Uani 1 1 d . . .
C2 C -0.0945(4) 0.1048(4) 0.7080(7) 0.0558(19) Uani 1 1 d . . .
C3 C -0.0967(4) 0.1781(4) 0.7057(6) 0.0529(17) Uani 1 1 d . . .
H3 H -0.1294 0.2028 0.6369 0.064 Uiso 1 1 calc R . .
C4 C -0.0491(4) 0.2159(3) 0.8084(6) 0.0436(15) Uani 1 1 d . . .
C5 C 0.0003(5) 0.1766(4) 0.9095(7) 0.0613(19) Uani 1 1 d . . .
H5 H 0.0338 0.2014 0.9782 0.074 Uiso 1 1 calc R . .
C6 C 0.0005(5) 0.1028(4) 0.9102(7) 0.067(2) Uani 1 1 d . . .
H6 H 0.0330 0.0778 0.9787 0.081 Uiso 1 1 calc R . .
C7 C -0.0463(4) 0.2960(4) 0.8151(6) 0.0468(16) Uani 1 1 d . . .
C8 C 0.0183(4) 0.3400(3) 0.8803(5) 0.0453(16) Uani 1 1 d . . .
C9 C 0.1009(4) 0.3392(4) 0.9526(6) 0.0492(16) Uani 1 1 d . . .
C10 C 0.0566(4) 0.4580(4) 0.9119(6) 0.0491(16) Uani 1 1 d . . .
C11 C -0.0069(4) 0.4138(3) 0.8567(5) 0.0422(15) Uani 1 1 d . . .
C12 C -0.0901(4) 0.4147(4) 0.7744(6) 0.0501(17) Uani 1 1 d . . .
C13 C 0.0581(4) 0.5375(4) 0.9102(6) 0.0485(16) Uani 1 1 d . . .
C14 C 0.1040(4) 0.5765(4) 0.8997(7) 0.064(2) Uani 1 1 d . . .
H14 H 0.1362 0.5522 0.8939 0.077 Uiso 1 1 calc R . .
C15 C 0.1025(5) 0.6520(4) 0.8975(7) 0.069(2) Uani 1 1 d . . .
H15 H 0.1337 0.6774 0.8905 0.082 Uiso 1 1 calc R . .
C16 C 0.0550(4) 0.6888(4) 0.9057(6) 0.0577(19) Uani 1 1 d . . .
C17 C 0.0066(5) 0.6504(4) 0.9102(6) 0.063(2) Uani 1 1 d . . .
H17 H -0.0280 0.6752 0.9106 0.075 Uiso 1 1 calc R . .
C18 C 0.0080(4) 0.5761(4) 0.9142(6) 0.0543(18) Uani 1 1 d . . .
H18 H -0.0244 0.5515 0.9194 0.065 Uiso 1 1 calc R . .
C19 C -0.1916(4) 0.3195(4) 0.6917(6) 0.067(2) Uani 1 1 d D . .
H19A H -0.2029 0.2727 0.6558 0.080 Uiso 1 1 calc R . .
H19B H -0.2269 0.3545 0.6328 0.080 Uiso 1 1 calc R . .
C20 C -0.2033(4) 0.3160(5) 0.7772(6) 0.079(2) Uani 1 1 d D . .
H20A H -0.1768 0.2738 0.8251 0.095 Uiso 1 1 calc R . .
H20B H -0.1800 0.3583 0.8258 0.095 Uiso 1 1 calc R . .
C21 C -0.2886(4) 0.3124(6) 0.7193(7) 0.097(3) Uani 1 1 d D . .
H21A H -0.3130 0.2719 0.6670 0.116 Uiso 1 1 calc R . .
H21B H -0.3145 0.3561 0.6757 0.116 Uiso 1 1 calc R . .
C22 C -0.2979(7) 0.3037(7) 0.8069(9) 0.124(4) Uani 1 1 d D . .
H22A H -0.2658 0.2649 0.8579 0.187 Uiso 1 1 calc R . .
H22B H -0.3508 0.2931 0.7680 0.187 Uiso 1 1 calc R . .
H22C H -0.2830 0.3477 0.8493 0.187 Uiso 1 1 calc R . .
C23 C 0.2030(5) 0.4352(5) 1.0547(8) 0.103(4) Uani 1 1 d D . .
H23A H 0.2124 0.4697 1.0187 0.123 Uiso 1 1 calc R . .
H23B H 0.2339 0.3928 1.0726 0.123 Uiso 1 1 calc R . .
C24 C 0.2338(8) 0.4683(7) 1.1677(9) 0.175(8) Uani 1 1 d D . .
H24A H 0.2849 0.4883 1.2100 0.211 Uiso 1 1 calc R . .
H24B H 0.1998 0.5059 1.1549 0.211 Uiso 1 1 calc R . .
C25 C 0.2357(12) 0.4040(8) 1.2313(14) 0.168(7) Uani 1 1 d D . .
H25A H 0.2555 0.3604 1.2246 0.201 Uiso 1 1 calc R . .
H25B H 0.1858 0.3945 1.2080 0.201 Uiso 1 1 calc R . .
C26 C 0.2932(7) 0.4381(8) 1.3505(15) 0.252(14) Uani 1 1 d D . .
H26A H 0.2808 0.4881 1.3462 0.379 Uiso 1 1 calc R . .
H26B H 0.3445 0.4338 1.3787 0.379 Uiso 1 1 calc R . .
H26C H 0.2901 0.4135 1.4011 0.379 Uiso 1 1 calc R . .
F1 F -0.1373(5) 0.0690(5) 0.6122(10) 0.186(4) Uani 1 1 d . . .
N1 N 0.1216(3) 0.4137(3) 0.9700(5) 0.0526(14) Uani 1 1 d . . .
N2 N -0.1116(3) 0.3402(3) 0.7502(5) 0.0499(14) Uani 1 1 d . . .
O1 O 0.1491(3) 0.2900(3) 0.9967(4) 0.0650(14) Uani 1 1 d . . .
O2 O -0.1378(3) 0.4642(3) 0.7297(5) 0.0664(14) 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
Br1 C16 1.894(8) . ?
Br2 C1 1.906(8) . ?
C1 C6 1.377(12) . ?
C1 C2 1.389(11) . ?
C2 F1 1.306(12) . ?
C2 C3 1.358(10) . ?
C3 C4 1.395(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(10) . ?
C4 C7 1.485(9) . ?
C5 C6 1.368(11) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.386(9) . ?
C7 N2 1.399(8) . ?
C8 C11 1.435(9) . ?
C8 C9 1.440(10) . ?
C9 O1 1.237(8) . ?
C9 N1 1.427(9) . ?
C10 C11 1.377(9) . ?
C10 N1 1.398(9) . ?
C10 C13 1.473(9) . ?
C11 C12 1.443(10) . ?
C12 O2 1.235(8) . ?
C12 N2 1.431(9) . ?
C13 C14 1.386(10) . ?
C13 C18 1.404(10) . ?
C14 C15 1.398(11) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(11) . ?
C17 C18 1.377(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.476(9) . ?
C19 C20 1.541(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.539(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.539(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N1 1.471(10) . ?
C23 C24 1.538(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.537(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.540(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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
C6 C1 C2 118.7(7) . . ?
C6 C1 Br2 121.1(6) . . ?
C2 C1 Br2 120.2(7) . . ?
F1 C2 C3 119.4(9) . . ?
F1 C2 C1 118.1(8) . . ?
C3 C2 C1 122.5(7) . . ?
C2 C3 C4 118.9(7) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.5(7) . . ?
C5 C4 C7 118.3(6) . . ?
C3 C4 C7 123.1(6) . . ?
C6 C5 C4 121.7(8) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 119.5(7) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 N2 108.1(6) . . ?
C8 C7 C4 128.0(6) . . ?
N2 C7 C4 123.9(6) . . ?
C7 C8 C11 108.4(6) . . ?
C7 C8 C9 142.7(6) . . ?
C11 C8 C9 108.4(5) . . ?
O1 C9 N1 122.7(6) . . ?
O1 C9 C8 133.3(6) . . ?
N1 C9 C8 104.0(5) . . ?
C11 C10 N1 107.6(6) . . ?
C11 C10 C13 127.7(6) . . ?
N1 C10 C13 124.8(6) . . ?
C10 C11 C8 108.7(6) . . ?
C10 C11 C12 142.4(6) . . ?
C8 C11 C12 108.4(5) . . ?
O2 C12 N2 122.8(6) . . ?
O2 C12 C11 132.8(6) . . ?
N2 C12 C11 104.5(5) . . ?
C14 C13 C18 117.8(7) . . ?
C14 C13 C10 123.6(6) . . ?
C18 C13 C10 118.5(6) . . ?
C13 C14 C15 121.0(7) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.1(7) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.0(7) . . ?
C17 C16 Br1 121.6(6) . . ?
C15 C16 Br1 119.4(6) . . ?
C16 C17 C18 121.7(7) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C13 120.1(7) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
N2 C19 C20 110.3(6) . . ?
N2 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
N2 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 113.0(6) . . ?
C21 C20 H20A 109.0 . . ?
C19 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 C22 111.6(7) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 119.0(9) . . ?
N1 C23 H23A 107.6 . . ?
C24 C23 H23A 107.6 . . ?
N1 C23 H23B 107.6 . . ?
C24 C23 H23B 107.6 . . ?
H23A C23 H23B 107.0 . . ?
C25 C24 C23 103.6(10) . . ?
C25 C24 H24A 111.0 . . ?
C23 C24 H24A 111.0 . . ?
C25 C24 H24B 111.0 . . ?
C23 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
C24 C25 C26 95.8(14) . . ?
C24 C25 H25A 112.6 . . ?
C26 C25 H25A 112.6 . . ?
C24 C25 H25B 112.6 . . ?
C26 C25 H25B 112.6 . . ?
H25A C25 H25B 110.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C10 N1 C9 111.3(5) . . ?
C10 N1 C23 127.8(6) . . ?
C9 N1 C23 120.1(6) . . ?
C7 N2 C12 110.7(5) . . ?
C7 N2 C19 127.5(6) . . ?
C12 N2 C19 119.3(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
C6 C1 C2 F1 176.8(8) . . . . ?
Br2 C1 C2 F1 -3.3(10) . . . . ?
C6 C1 C2 C3 -2.7(11) . . . . ?
Br2 C1 C2 C3 177.1(6) . . . . ?
F1 C2 C3 C4 -178.1(7) . . . . ?
C1 C2 C3 C4 1.4(11) . . . . ?
C2 C3 C4 C5 1.3(10) . . . . ?
C2 C3 C4 C7 179.1(6) . . . . ?
C3 C4 C5 C6 -2.7(11) . . . . ?
C7 C4 C5 C6 179.4(7) . . . . ?
C4 C5 C6 C1 1.5(12) . . . . ?
C2 C1 C6 C5 1.2(11) . . . . ?
Br2 C1 C6 C5 -178.6(6) . . . . ?
C5 C4 C7 C8 44.7(10) . . . . ?
C3 C4 C7 C8 -133.1(7) . . . . ?
C5 C4 C7 N2 -137.9(7) . . . . ?
C3 C4 C7 N2 44.3(10) . . . . ?
N2 C7 C8 C11 0.5(8) . . . . ?
C4 C7 C8 C11 178.3(6) . . . . ?
N2 C7 C8 C9 -169.1(9) . . . . ?
C4 C7 C8 C9 8.6(15) . . . . ?
C7 C8 C9 O1 -11.3(16) . . . . ?
C11 C8 C9 O1 179.1(8) . . . . ?
C7 C8 C9 N1 170.2(9) . . . . ?
C11 C8 C9 N1 0.5(7) . . . . ?
N1 C10 C11 C8 0.0(7) . . . . ?
C13 C10 C11 C8 178.8(6) . . . . ?
N1 C10 C11 C12 -170.7(9) . . . . ?
C13 C10 C11 C12 8.0(14) . . . . ?
C7 C8 C11 C10 -173.8(6) . . . . ?
C9 C8 C11 C10 -0.4(8) . . . . ?
C7 C8 C11 C12 0.3(8) . . . . ?
C9 C8 C11 C12 173.7(6) . . . . ?
C10 C11 C12 O2 -10.9(16) . . . . ?
C8 C11 C12 O2 178.3(8) . . . . ?
C10 C11 C12 N2 169.8(9) . . . . ?
C8 C11 C12 N2 -1.0(7) . . . . ?
C11 C10 C13 C14 -137.1(8) . . . . ?
N1 C10 C13 C14 41.5(11) . . . . ?
C11 C10 C13 C18 39.8(10) . . . . ?
N1 C10 C13 C18 -141.6(7) . . . . ?
C18 C13 C14 C15 2.5(11) . . . . ?
C10 C13 C14 C15 179.4(7) . . . . ?
C13 C14 C15 C16 -0.1(12) . . . . ?
C14 C15 C16 C17 -3.2(11) . . . . ?
C14 C15 C16 Br1 176.8(6) . . . . ?
C15 C16 C17 C18 4.3(11) . . . . ?
Br1 C16 C17 C18 -175.7(5) . . . . ?
C16 C17 C18 C13 -1.9(11) . . . . ?
C14 C13 C18 C17 -1.5(10) . . . . ?
C10 C13 C18 C17 -178.6(6) . . . . ?
N2 C19 C20 C21 166.5(7) . . . . ?
C19 C20 C21 C22 176.1(9) . . . . ?
N1 C23 C24 C25 71.4(14) . . . . ?
C23 C24 C25 C26 160.1(11) . . . . ?
C11 C10 N1 C9 0.3(8) . . . . ?
C13 C10 N1 C9 -178.5(6) . . . . ?
C11 C10 N1 C23 -169.7(8) . . . . ?
C13 C10 N1 C23 11.5(12) . . . . ?
O1 C9 N1 C10 -179.3(7) . . . . ?
C8 C9 N1 C10 -0.5(8) . . . . ?
O1 C9 N1 C23 -8.4(11) . . . . ?
C8 C9 N1 C23 170.3(7) . . . . ?
C24 C23 N1 C10 63.7(13) . . . . ?
C24 C23 N1 C9 -105.5(10) . . . . ?
C8 C7 N2 C12 -1.2(8) . . . . ?
C4 C7 N2 C12 -179.0(6) . . . . ?
C8 C7 N2 C19 -162.8(6) . . . . ?
C4 C7 N2 C19 19.4(11) . . . . ?
O2 C12 N2 C7 -178.1(7) . . . . ?
C11 C12 N2 C7 1.3(7) . . . . ?
O2 C12 N2 C19 -14.8(10) . . . . ?
C11 C12 N2 C19 164.6(6) . . . . ?
C20 C19 N2 C7 79.3(9) . . . . ?
C20 C19 N2 C12 -80.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.587
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1440590'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br F N O'
_chemical_formula_weight         141.94

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.213(4)
_cell_length_b                   18.364(3)
_cell_length_c                   15.662(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 131.740(2)
_cell_angle_gamma                90.00
_cell_volume                     4981.7(14)
_cell_formula_units_Z            54
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3564
_exptl_absorpt_coefficient_mu    10.965
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15415
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.54
_reflns_number_total             5720
_reflns_number_gt                2911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1773P)²+8.3707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5720
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0844
_refine_ls_wR_factor_ref         0.3129
_refine_ls_wR_factor_gt          0.2662
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.05916(7) 1.29102(4) 0.41009(8) 0.0957(4) Uani 1 1 d . . .
Br2 Br 0.94766(6) 0.46220(4) 0.30313(10) 0.0972(5) Uani 1 1 d . . .
C1 C 0.9050(4) 0.6036(4) 0.2061(6) 0.0529(15) Uani 1 1 d . . .
C2 C 0.9512(4) 0.5646(3) 0.3056(7) 0.0592(18) Uani 1 1 d . . .
C3 C 1.0003(5) 0.6018(4) 0.4102(7) 0.071(2) Uani 1 1 d . . .
H3 H 1.0323 0.5760 0.4787 0.085 Uiso 1 1 calc R . .
C4 C 1.0007(4) 0.6768(4) 0.4105(6) 0.0594(17) Uani 1 1 d . . .
H4 H 1.0346 0.7016 0.4797 0.071 Uiso 1 1 calc R . .
C5 C 0.9509(3) 0.7165(3) 0.3081(5) 0.0453(13) Uani 1 1 d . . .
C6 C 0.9021(4) 0.6791(3) 0.2033(6) 0.0497(14) Uani 1 1 d . . .
H6 H 0.8689 0.7042 0.1343 0.060 Uiso 1 1 calc R . .
C7 C 0.9541(3) 0.7952(3) 0.3140(5) 0.0455(13) Uani 1 1 d . . .
C8 C 1.0185(4) 0.8398(3) 0.3795(5) 0.0459(14) Uani 1 1 d . . .
C9 C 0.9939(3) 0.9134(3) 0.3568(5) 0.0434(13) Uani 1 1 d . . .
C10 C 0.9116(4) 0.9154(3) 0.2745(6) 0.0493(14) Uani 1 1 d . . .
C11 C 1.1013(4) 0.8376(3) 0.4533(5) 0.0490(14) Uani 1 1 d . . .
C12 C 1.0572(4) 0.9577(3) 0.4128(5) 0.0477(14) Uani 1 1 d . . .
C13 C 1.0075(4) 1.0762(4) 0.4118(5) 0.0558(16) Uani 1 1 d . . .
H13 H 0.9740 1.0516 0.4150 0.067 Uiso 1 1 calc R . .
C14 C 1.0593(3) 1.0370(3) 0.4114(5) 0.0478(14) Uani 1 1 d . . .
C15 C 1.1071(4) 1.0758(4) 0.4042(6) 0.0619(18) Uani 1 1 d . . .
H15 H 1.1412 1.0511 0.4023 0.074 Uiso 1 1 calc R . .
C16 C 1.1046(5) 1.1501(4) 0.4000(7) 0.075(2) Uani 1 1 d . . .
H16 H 1.1359 1.1750 0.3926 0.089 Uiso 1 1 calc R . .
C17 C 1.0563(4) 1.1893(4) 0.4064(5) 0.0607(18) Uani 1 1 d . . .
C18 C 1.0065(4) 1.1493(4) 0.4074(6) 0.0578(17) Uani 1 1 d . . .
C19 C 0.8099(4) 0.8194(4) 0.1897(6) 0.0635(18) Uani 1 1 d . . .
H19A H 0.7996 0.7717 0.1555 0.076 Uiso 1 1 calc R . .
H19B H 0.7748 0.8539 0.1289 0.076 Uiso 1 1 calc R . .
C20 C 0.7961(5) 0.8176(6) 0.2763(7) 0.084(2) Uani 1 1 d . . .
H20A H 0.8223 0.7755 0.3258 0.101 Uiso 1 1 calc R . .
H20B H 0.8190 0.8607 0.3240 0.101 Uiso 1 1 calc R . .
C21 C 0.7127(5) 0.8144(6) 0.2188(9) 0.100(3) Uani 1 1 d . . .
H21A H 0.6868 0.8578 0.1724 0.120 Uiso 1 1 calc R . .
H21B H 0.6889 0.7726 0.1681 0.120 Uiso 1 1 calc R . .
C22 C 0.7014(7) 0.8090(7) 0.3016(12) 0.118(4) Uani 1 1 d . . .
H22A H 0.7266 0.7661 0.3475 0.177 Uiso 1 1 calc R . .
H22B H 0.6472 0.8064 0.2605 0.177 Uiso 1 1 calc R . .
H22C H 0.7230 0.8512 0.3501 0.177 Uiso 1 1 calc R . .
C23 C 1.2035(5) 0.9333(5) 0.5624(9) 0.103(4) Uani 1 1 d . . .
H23A H 1.2147 0.9776 0.5421 0.124 Uiso 1 1 calc R . .
H23B H 1.2365 0.8948 0.5737 0.124 Uiso 1 1 calc R . .
C24 C 1.2179(8) 0.9456(10) 0.6759(11) 0.239(13) Uani 1 1 d . . .
H24A H 1.2323 0.9963 0.6964 0.287 Uiso 1 1 calc R . .
H24B H 1.1678 0.9405 0.6536 0.287 Uiso 1 1 calc R . .
C25 C 1.256(2) 0.9163(14) 0.752(2) 0.302(19) Uani 1 1 d . . .
H25A H 1.2983 0.9029 0.7553 0.362 Uiso 1 1 calc R . .
H25B H 1.2297 0.8714 0.7394 0.362 Uiso 1 1 calc R . .
C26 C 1.2938(8) 0.9399(8) 0.8694(16) 0.178(8) Uani 1 1 d . . .
H26A H 1.2663 0.9807 0.8655 0.266 Uiso 1 1 calc R . .
H26B H 1.3462 0.9538 0.9097 0.266 Uiso 1 1 calc R . .
H26C H 1.2932 0.9004 0.9090 0.266 Uiso 1 1 calc R . .
F1 F 0.8604(3) 0.5677(3) 0.1049(4) 0.0851(13) Uani 1 1 d . . .
F2 F 0.9551(6) 1.1861(5) 0.3940(9) 0.178(3) Uani 1 1 d . . .
N1 N 0.8895(3) 0.8403(3) 0.2497(4) 0.0497(12) Uani 1 1 d . . .
N2 N 1.1221(3) 0.9133(3) 0.4718(5) 0.0533(13) Uani 1 1 d . . .
O1 O 0.8645(3) 0.9651(2) 0.2305(5) 0.0674(13) Uani 1 1 d . . .
O2 O 1.1485(3) 0.7893(2) 0.4958(4) 0.0610(12) 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
Br1 C17 1.868(7) . ?
Br2 C2 1.882(6) . ?
C1 F1 1.354(8) . ?
C1 C2 1.366(10) . ?
C1 C6 1.387(9) . ?
C2 C3 1.401(11) . ?
C3 C4 1.378(10) . ?
C4 C5 1.404(9) . ?
C5 C6 1.405(9) . ?
C5 C7 1.448(8) . ?
C7 C8 1.383(9) . ?
C7 N1 1.393(8) . ?
C8 C9 1.417(8) . ?
C8 C11 1.439(9) . ?
C9 C12 1.371(9) . ?
C9 C10 1.426(9) . ?
C10 O1 1.225(7) . ?
C10 N1 1.432(8) . ?
C11 O2 1.209(7) . ?
C11 N2 1.437(8) . ?
C12 N2 1.391(8) . ?
C12 C14 1.458(8) . ?
C13 C18 1.343(9) . ?
C13 C14 1.404(9) . ?
C14 C15 1.385(9) . ?
C15 C16 1.365(11) . ?
C16 C17 1.391(11) . ?
C17 C18 1.380(10) . ?
C18 F2 1.260(11) . ?
C19 N1 1.460(8) . ?
C19 C20 1.589(12) . ?
C20 C21 1.496(12) . ?
C21 C22 1.488(15) . ?
C23 N2 1.466(10) . ?
C23 C24 1.59(2) . ?
C24 C25 1.04(2) . ?
C25 C26 1.49(3) . ?

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
F1 C1 C2 119.2(6) . . ?
F1 C1 C6 117.9(6) . . ?
C2 C1 C6 123.0(6) . . ?
C1 C2 C3 119.3(6) . . ?
C1 C2 Br2 120.7(6) . . ?
C3 C2 Br2 120.0(6) . . ?
C4 C3 C2 119.3(7) . . ?
C3 C4 C5 121.1(7) . . ?
C4 C5 C6 119.5(6) . . ?
C4 C5 C7 118.5(6) . . ?
C6 C5 C7 122.0(6) . . ?
C1 C6 C5 117.8(6) . . ?
C8 C7 N1 107.2(5) . . ?
C8 C7 C5 128.6(6) . . ?
N1 C7 C5 124.2(5) . . ?
C7 C8 C9 108.8(5) . . ?
C7 C8 C11 141.6(6) . . ?
C9 C8 C11 109.2(5) . . ?
C12 C9 C8 108.9(5) . . ?
C12 C9 C10 141.6(6) . . ?
C8 C9 C10 109.0(5) . . ?
O1 C10 C9 133.2(6) . . ?
O1 C10 N1 122.8(6) . . ?
C9 C10 N1 104.0(5) . . ?
O2 C11 N2 122.6(6) . . ?
O2 C11 C8 134.4(6) . . ?
N2 C11 C8 103.0(5) . . ?
C9 C12 N2 107.6(5) . . ?
C9 C12 C14 128.0(6) . . ?
N2 C12 C14 124.3(6) . . ?
C18 C13 C14 119.9(6) . . ?
C15 C14 C13 118.1(6) . . ?
C15 C14 C12 123.5(6) . . ?
C13 C14 C12 118.4(6) . . ?
C16 C15 C14 120.5(7) . . ?
C15 C16 C17 121.7(7) . . ?
C18 C17 C16 116.5(7) . . ?
C18 C17 Br1 123.0(6) . . ?
C16 C17 Br1 120.5(6) . . ?
F2 C18 C13 121.8(8) . . ?
F2 C18 C17 114.8(8) . . ?
C13 C18 C17 123.1(6) . . ?
N1 C19 C20 110.1(6) . . ?
C21 C20 C19 113.8(7) . . ?
C22 C21 C20 112.7(9) . . ?
N2 C23 C24 107.1(10) . . ?
C25 C24 C23 125.7(14) . . ?
C24 C25 C26 128(2) . . ?
C7 N1 C10 110.9(5) . . ?
C7 N1 C19 127.0(5) . . ?
C10 N1 C19 120.0(5) . . ?
C12 N2 C11 111.3(5) . . ?
C12 N2 C23 128.6(6) . . ?
C11 N2 C23 118.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         3.240
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.166
####################################################################### 
# 
# 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_h
_database_code_depnum_ccdc_archive 'CCDC 1440591'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br F N O'
_chemical_formula_weight         141.94

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Pc   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   12.990(3)
_cell_length_b                   4.2334(10)
_cell_length_c                   17.997(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.476(2)
_cell_angle_gamma                90.00
_cell_volume                     969.9(4)
_cell_formula_units_Z            11
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             726
_exptl_absorpt_coefficient_mu    11.472
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5633
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.55
_reflns_number_total             3722
_reflns_number_gt                2702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.6779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.38(2)
_refine_ls_number_reflns         3722
_refine_ls_number_parameters     264
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.33116(4) 0.8249(3) 0.38282(3) 0.0563(4) Uani 1 1 d . . .
Br2 Br 0.78602(4) -0.3253(3) 0.72101(3) 0.0541(4) Uani 1 1 d . . .
C1 C -0.1975(7) 0.692(2) 0.4319(6) 0.035(2) Uani 1 1 d . . .
C2 C -0.1109(7) 0.758(2) 0.4022(5) 0.039(2) Uani 1 1 d . . .
H2 H -0.1181 0.8647 0.3563 0.047 Uiso 1 1 calc R . .
C3 C -0.0070(6) 0.6600(19) 0.4427(4) 0.030(2) Uani 1 1 d . . .
H3 H 0.0537 0.7052 0.4247 0.036 Uiso 1 1 calc R . .
C4 C -0.0044(7) 0.493(2) 0.5107(5) 0.030(2) Uani 1 1 d . . .
C5 C -0.0903(7) 0.429(2) 0.5368(5) 0.037(2) Uani 1 1 d . . .
C6 C -0.1924(7) 0.519(2) 0.4975(6) 0.040(2) Uani 1 1 d . . .
H6 H -0.2526 0.4630 0.5151 0.048 Uiso 1 1 calc R . .
C7 C 0.1071(7) 0.403(2) 0.5514(5) 0.0298(19) Uani 1 1 d . . .
C8 C 0.2457(6) 0.3271(19) 0.6524(5) 0.027(2) Uani 1 1 d . . .
C9 C 0.2708(7) 0.226(2) 0.5788(5) 0.035(2) Uani 1 1 d . . .
C10 C 0.1836(6) 0.284(2) 0.5201(5) 0.0275(18) Uani 1 1 d . . .
C11 C 0.2095(7) 0.173(2) 0.4533(5) 0.039(2) Uani 1 1 d . . .
C12 C 0.3552(7) 0.096(2) 0.5502(5) 0.0284(19) Uani 1 1 d . . .
C13 C 0.0896(7) 0.591(2) 0.6843(5) 0.037(2) Uani 1 1 d . . .
H13A H 0.1396 0.7453 0.7100 0.044 Uiso 1 1 calc R . .
H13B H 0.0297 0.7075 0.6566 0.044 Uiso 1 1 calc R . .
C14 C 0.0555(7) 0.406(2) 0.7395(5) 0.042(2) Uani 1 1 d . . .
H14A H 0.0053 0.2534 0.7151 0.063 Uiso 1 1 calc R . .
H14B H 0.0234 0.5391 0.7716 0.063 Uiso 1 1 calc R . .
H14C H 0.1146 0.2986 0.7695 0.063 Uiso 1 1 calc R . .
C15 C 0.3623(7) -0.117(2) 0.4178(5) 0.031(2) Uani 1 1 d . . .
H15A H 0.3111 -0.2687 0.3924 0.038 Uiso 1 1 calc R . .
H15B H 0.4219 -0.2346 0.4455 0.038 Uiso 1 1 calc R . .
C16 C 0.4003(8) 0.101(2) 0.3554(5) 0.041(2) Uani 1 1 d . . .
H16A H 0.3441 0.2380 0.3326 0.062 Uiso 1 1 calc R . .
H16B H 0.4201 -0.0307 0.3171 0.062 Uiso 1 1 calc R . .
H16C H 0.4596 0.2250 0.3793 0.062 Uiso 1 1 calc R . .
C17 C 0.4540(7) -0.002(2) 0.5887(5) 0.0264(19) Uani 1 1 d . . .
C18 C 0.4726(7) -0.160(2) 0.6573(5) 0.041(2) Uani 1 1 d . . .
H18 H 0.4142 -0.2033 0.6781 0.050 Uiso 1 1 calc R . .
C19 C 0.5625(8) -0.255(3) 0.6957(5) 0.044(2) Uani 1 1 d . . .
H19 H 0.5666 -0.3701 0.7402 0.053 Uiso 1 1 calc R . .
C20 C 0.6526(7) -0.180(2) 0.6686(5) 0.037(2) Uani 1 1 d . . .
C21 C 0.6424(8) -0.021(2) 0.6018(6) 0.040(2) Uani 1 1 d . . .
H21 H 0.7022 0.0221 0.5825 0.048 Uiso 1 1 calc R . .
C22 C 0.5490(7) 0.076(2) 0.5630(5) 0.040(2) Uani 1 1 d . . .
H22 H 0.5455 0.1938 0.5190 0.048 Uiso 1 1 calc R . .
F1 F -0.0902(2) 0.2213(8) 0.59160(19) 0.0503(8) Uani 1 1 d . . .
N1 N 0.1382(6) 0.4226(18) 0.6295(4) 0.0305(17) Uani 1 1 d . . .
N2 N 0.3153(5) 0.0668(18) 0.4719(4) 0.0308(17) Uani 1 1 d . . .
O1 O 0.2944(6) 0.3453(15) 0.7154(4) 0.0456(17) Uani 1 1 d . . .
O2 O 0.1584(6) 0.1538(14) 0.3860(4) 0.0395(17) 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
Br1 C1 1.871(9) . ?
Br2 C20 1.903(8) . ?
C1 C2 1.366(11) . ?
C1 C6 1.382(13) . ?
C2 C3 1.461(11) . ?
C3 C4 1.408(11) . ?
C4 C5 1.323(11) . ?
C4 C7 1.534(11) . ?
C5 F1 1.320(9) . ?
C5 C6 1.425(13) . ?
C7 C10 1.335(11) . ?
C7 N1 1.386(10) . ?
C8 O1 1.185(11) . ?
C8 N1 1.434(10) . ?
C8 C9 1.489(11) . ?
C9 C10 1.408(5) . ?
C9 C12 1.411(11) . ?
C10 C11 1.394(12) . ?
C11 O2 1.262(12) . ?
C11 N2 1.421(11) . ?
C12 C17 1.396(12) . ?
C12 N2 1.408(11) . ?
C13 C14 1.406(12) . ?
C13 N1 1.459(10) . ?
C15 N2 1.470(10) . ?
C15 C16 1.606(11) . ?
C17 C18 1.382(12) . ?
C17 C22 1.439(11) . ?
C18 C19 1.296(13) . ?
C19 C20 1.393(12) . ?
C20 C21 1.360(12) . ?
C21 C22 1.337(13) . ?

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 122.6(8) . . ?
C2 C1 Br1 120.9(7) . . ?
C6 C1 Br1 116.4(7) . . ?
C1 C2 C3 119.9(8) . . ?
C4 C3 C2 115.9(8) . . ?
C5 C4 C3 122.4(8) . . ?
C5 C4 C7 124.2(8) . . ?
C3 C4 C7 113.4(7) . . ?
F1 C5 C4 121.7(8) . . ?
F1 C5 C6 114.3(8) . . ?
C4 C5 C6 122.4(8) . . ?
C1 C6 C5 116.6(9) . . ?
C10 C7 N1 111.0(7) . . ?
C10 C7 C4 127.2(8) . . ?
N1 C7 C4 121.7(7) . . ?
O1 C8 N1 124.1(7) . . ?
O1 C8 C9 134.5(8) . . ?
N1 C8 C9 101.4(7) . . ?
C10 C9 C12 111.2(6) . . ?
C10 C9 C8 109.4(5) . . ?
C12 C9 C8 139.4(9) . . ?
C7 C10 C11 145.0(8) . . ?
C7 C10 C9 107.8(5) . . ?
C11 C10 C9 107.0(6) . . ?
O2 C11 C10 132.7(9) . . ?
O2 C11 N2 120.3(8) . . ?
C10 C11 N2 106.9(8) . . ?
C17 C12 N2 126.1(7) . . ?
C17 C12 C9 129.8(8) . . ?
N2 C12 C9 104.0(8) . . ?
C14 C13 N1 116.3(8) . . ?
N2 C15 C16 112.6(7) . . ?
C18 C17 C12 124.6(8) . . ?
C18 C17 C22 112.9(8) . . ?
C12 C17 C22 122.4(8) . . ?
C19 C18 C17 127.3(9) . . ?
C18 C19 C20 118.2(9) . . ?
C21 C20 C19 118.7(8) . . ?
C21 C20 Br2 121.2(7) . . ?
C19 C20 Br2 119.9(7) . . ?
C22 C21 C20 122.1(9) . . ?
C21 C22 C17 120.6(9) . . ?
C7 N1 C8 110.2(6) . . ?
C7 N1 C13 129.5(8) . . ?
C8 N1 C13 118.2(7) . . ?
C12 N2 C11 110.7(7) . . ?
C12 N2 C15 126.2(8) . . ?
C11 N2 C15 121.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_a50317b
_database_code_depnum_ccdc_archive 'CCDC 1440592'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2016-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 Br2 F2 N2 O4'
_chemical_formula_weight         682.39

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                   7.389(3)
_cell_length_b                   8.698(3)
_cell_length_c                   12.870(5)
_cell_angle_alpha                70.950(5)
_cell_angle_beta                 73.447(4)
_cell_angle_gamma                74.305(4)
_cell_volume                     734.9(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    866
_cell_measurement_theta_min      2.933
_cell_measurement_theta_max      25.386

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             346
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.808
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3067
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             2533
_reflns_number_gt                1948
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1179P)²] 
 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         2533
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.18706(8) -0.14923(7) 0.84346(5) 0.0599(3) Uani 1 1 d . . . . .
F1 F 0.7319(4) 0.0965(4) 0.8626(3) 0.0563(8) Uani 1 1 d . . . . .
O1 O 0.8284(5) 0.6416(5) 0.8441(3) 0.0532(9) Uani 1 1 d . . . . .
N1 N 0.6591(5) 0.4557(5) 0.8429(3) 0.0397(9) Uani 1 1 d . . . . .
C1 C 0.7014(7) 0.5640(6) 0.8897(4) 0.0391(11) Uani 1 1 d . . . . .
C2 C 0.5002(6) 0.3860(5) 0.9116(4) 0.0353(10) Uani 1 1 d . . . . .
C3 C 0.4402(6) 0.4466(5) 1.0044(3) 0.0366(10) Uani 1 1 d . . . . .
C4 C 0.4268(6) 0.2649(6) 0.8868(3) 0.0360(10) Uani 1 1 d . . . . .
C5 C 0.5438(6) 0.1221(5) 0.8650(3) 0.0338(10) Uani 1 1 d . . . . .
C6 C 0.4790(6) -0.0005(6) 0.8495(4) 0.0377(10) Uani 1 1 d . . . . .
H6 H 0.5638 -0.0946 0.8333 0.045 Uiso 1 1 calc R U . . .
C7 C 0.2841(7) 0.0200(6) 0.8588(4) 0.0406(11) Uani 1 1 d . . . . .
C8 C 0.1592(7) 0.1622(6) 0.8813(4) 0.0467(12) Uani 1 1 d . . . . .
H8 H 0.0278 0.1752 0.8870 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2297(7) 0.2838(6) 0.8950(4) 0.0435(11) Uani 1 1 d . . . . .
H9 H 0.1458 0.3790 0.9098 0.052 Uiso 1 1 calc R U . . .
C10 C 0.7410(7) 0.4567(6) 0.7246(4) 0.0446(11) Uani 1 1 d . . . . .
H10A H 0.7450 0.3494 0.7154 0.054 Uiso 1 1 calc R U . . .
H10B H 0.8721 0.4743 0.7045 0.054 Uiso 1 1 calc R U . . .
C11 C 0.6260(8) 0.5900(7) 0.6461(4) 0.0515(12) Uani 1 1 d . . . . .
H11A H 0.6115 0.6963 0.6599 0.062 Uiso 1 1 calc R U . . .
H11B H 0.4985 0.5666 0.6610 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7245(9) 0.5992(8) 0.5234(4) 0.0628(16) Uani 1 1 d . . . . .
H12A H 0.8531 0.6197 0.5096 0.075 Uiso 1 1 calc R U . . .
H12B H 0.7370 0.4930 0.5099 0.075 Uiso 1 1 calc R U . . .
C13 C 0.6163(11) 0.7339(10) 0.4410(6) 0.091(2) Uani 1 1 d . . . . .
H13A H 0.4956 0.7065 0.4470 0.136 Uiso 1 1 calc R U . . .
H13B H 0.6916 0.7424 0.3657 0.136 Uiso 1 1 calc R U . . .
H13C H 0.5932 0.8379 0.4581 0.136 Uiso 1 1 calc R U . . .
C14 C 0.9313(11) 0.1439(10) 0.4238(6) 0.085(2) Uani 1 1 d . . . . .
H14A H 0.9487 0.2521 0.3737 0.102 Uiso 1 1 calc R U . . .
H14B H 0.8145 0.1215 0.4165 0.102 Uiso 1 1 calc R U . . .
C15 C 0.9021(11) -0.0159(11) 0.6087(6) 0.093(3) Uani 1 1 d . . . . .
H15A H 0.7844 -0.0455 0.6091 0.111 Uiso 1 1 calc R U . . .
H15B H 0.8965 -0.0137 0.6844 0.111 Uiso 1 1 calc R U . . .
O2 O 0.9134(8) 0.1446(6) 0.5344(5) 0.0877(14) 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
Br1 C7 1.887(5) . ?
F1 C5 1.339(5) . ?
O1 C1 1.205(6) . ?
N1 C2 1.404(6) . ?
N1 C1 1.409(6) . ?
N1 C10 1.467(6) . ?
C1 C3 1.456(6) 2_667 ?
C2 C3 1.372(6) . ?
C2 C4 1.460(6) . ?
C3 C3 1.406(9) 2_667 ?
C3 C1 1.456(6) 2_667 ?
C4 C5 1.370(6) . ?
C4 C9 1.398(6) . ?
C5 C6 1.370(6) . ?
C6 C7 1.377(6) . ?
C7 C8 1.388(7) . ?
C8 C9 1.376(7) . ?
C10 C11 1.509(7) . ?
C11 C12 1.525(7) . ?
C12 C13 1.517(8) . ?
C14 O2 1.393(8) . ?
C14 C15 1.483(10) 2_756 ?
C15 O2 1.420(9) . ?
C15 C14 1.483(10) 2_756 ?

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 N1 C1 111.5(4) . . ?
C2 N1 C10 125.6(4) . . ?
C1 N1 C10 120.9(4) . . ?
O1 C1 N1 123.4(4) . . ?
O1 C1 C3 133.2(5) . 2_667 ?
N1 C1 C3 103.4(4) . 2_667 ?
C3 C2 N1 107.2(4) . . ?
C3 C2 C4 128.8(4) . . ?
N1 C2 C4 123.9(4) . . ?
C2 C3 C3 109.2(5) . 2_667 ?
C2 C3 C1 142.1(4) . 2_667 ?
C3 C3 C1 108.7(5) 2_667 2_667 ?
C5 C4 C9 117.3(4) . . ?
C5 C4 C2 121.9(4) . . ?
C9 C4 C2 120.5(4) . . ?
F1 C5 C6 117.3(4) . . ?
F1 C5 C4 118.7(4) . . ?
C6 C5 C4 123.9(4) . . ?
C5 C6 C7 117.8(4) . . ?
C6 C7 C8 120.6(4) . . ?
C6 C7 Br1 119.3(4) . . ?
C8 C7 Br1 120.1(4) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C4 120.4(4) . . ?
N1 C10 C11 112.2(4) . . ?
C10 C11 C12 111.1(4) . . ?
C13 C12 C11 113.1(5) . . ?
O2 C14 C15 110.6(6) . 2_756 ?
O2 C15 C14 112.3(6) . 2_756 ?
C14 O2 C15 110.6(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
C2 N1 C1 O1 -177.9(4) . . . . ?
C10 N1 C1 O1 -13.0(7) . . . . ?
C2 N1 C1 C3 1.7(5) . . . 2_667 ?
C10 N1 C1 C3 166.6(4) . . . 2_667 ?
C1 N1 C2 C3 -0.9(5) . . . . ?
C10 N1 C2 C3 -165.0(4) . . . . ?
C1 N1 C2 C4 -177.8(4) . . . . ?
C10 N1 C2 C4 18.1(7) . . . . ?
N1 C2 C3 C3 -0.3(6) . . . 2_667 ?
C4 C2 C3 C3 176.4(5) . . . 2_667 ?
N1 C2 C3 C1 -178.2(6) . . . 2_667 ?
C4 C2 C3 C1 -1.5(9) . . . 2_667 ?
C3 C2 C4 C5 -123.3(5) . . . . ?
N1 C2 C4 C5 53.0(6) . . . . ?
C3 C2 C4 C9 50.7(6) . . . . ?
N1 C2 C4 C9 -133.0(5) . . . . ?
C9 C4 C5 F1 -176.5(4) . . . . ?
C2 C4 C5 F1 -2.3(6) . . . . ?
C9 C4 C5 C6 0.8(6) . . . . ?
C2 C4 C5 C6 175.0(4) . . . . ?
F1 C5 C6 C7 176.0(4) . . . . ?
C4 C5 C6 C7 -1.3(7) . . . . ?
C5 C6 C7 C8 1.0(7) . . . . ?
C5 C6 C7 Br1 -177.8(3) . . . . ?
C6 C7 C8 C9 -0.3(7) . . . . ?
Br1 C7 C8 C9 178.5(4) . . . . ?
C7 C8 C9 C4 -0.2(7) . . . . ?
C5 C4 C9 C8 0.0(7) . . . . ?
C2 C4 C9 C8 -174.3(4) . . . . ?
C2 N1 C10 C11 79.3(6) . . . . ?
C1 N1 C10 C11 -83.4(6) . . . . ?
N1 C10 C11 C12 174.6(5) . . . . ?
C10 C11 C12 C13 -178.9(6) . . . . ?
C15 C14 O2 C15 -54.9(9) 2_756 . . . ?
C14 C15 O2 C14 55.8(10) 2_756 . . . ?

_refine_diff_density_max         0.814
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.161

_shelxl_version_number           2013-2

