# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_n3381
_database_code_depnum_ccdc_archive 'CCDC 1026790'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C Br3 N O2, Cl, C12 H28 N'
_chemical_formula_sum            'C13 H28 Br3 Cl N2 O2'
_chemical_formula_weight         519.55
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.0589(13)
_cell_length_b                   13.6380(9)
_cell_length_c                   18.3496(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.258(4)
_cell_angle_gamma                90
_cell_volume                     4001.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.565
_shelx_estimated_absorpt_T_min   0.108
_exptl_absorpt_coefficient_mu    6.187
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1359 before and 0.0939 after correction. The Ratio of minimum to maximum transmission is 0.5546. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.648
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.104
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1003
_diffrn_reflns_av_unetI/netI     0.0941
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            52204
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.036
_diffrn_reflns_theta_min         1.767
_diffrn_ambient_temperature      100.1
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Kappa Apex 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7522
_reflns_number_total             11363
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         1.646
_refine_diff_density_min         -0.971
_refine_diff_density_rms         0.195
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         11363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+33.2148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1750
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
  C25(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.37511(4) 0.44015(4) 0.56367(3) 0.02015(15) Uani 1 1 d . . . . .
Br2 Br 0.26568(4) 0.34590(4) 0.42915(3) 0.01969(14) Uani 1 1 d . . . . .
Br3 Br 0.46523(4) 0.34231(4) 0.43421(3) 0.01895(14) Uani 1 1 d . . . . .
O1 O 0.3283(5) 0.1721(4) 0.5089(4) 0.058(2) Uani 1 1 d . . . . .
O2 O 0.4297(4) 0.2272(4) 0.5808(3) 0.0495(17) Uani 1 1 d . . . . .
N1 N 0.3752(4) 0.2366(4) 0.5306(3) 0.0217(12) Uani 1 1 d . . . . .
C1 C 0.3690(4) 0.3367(4) 0.4915(3) 0.0174(12) Uani 1 1 d . . . . .
Br4 Br 0.88625(4) 0.42738(5) 0.56460(4) 0.02372(16) Uani 1 1 d . . . . .
Br5 Br 0.77479(4) 0.34292(4) 0.42798(3) 0.02095(15) Uani 1 1 d . . . . .
Br6 Br 0.97428(4) 0.34839(4) 0.42704(3) 0.02105(15) Uani 1 1 d . . . . .
O3 O 0.8617(4) 0.1608(3) 0.4803(4) 0.0508(17) Uani 1 1 d . . . . .
O4 O 0.9329(4) 0.2175(4) 0.5758(3) 0.0461(16) Uani 1 1 d . . . . .
N2 N 0.8907(4) 0.2280(4) 0.5175(4) 0.0282(13) Uani 1 1 d . . . . .
C2 C 0.8798(4) 0.3332(4) 0.4863(3) 0.0189(13) Uani 1 1 d . . . . .
Cl1 Cl 0.10828(10) 0.38185(11) 0.32718(8) 0.0212(3) Uani 1 1 d . . . . .
Cl2 Cl 0.60419(10) 0.37200(10) 0.33896(8) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.4193(4) 0.5590(3) 0.2112(3) 0.0187(11) Uani 1 1 d . . . . .
C3 C 0.3720(4) 0.6113(4) 0.2678(3) 0.0206(13) Uani 1 1 d . . . . .
H3A H 0.3113 0.6028 0.2543 0.025 Uiso 1 1 calc R . . . .
H3B H 0.3844 0.6823 0.2656 0.025 Uiso 1 1 calc R . . . .
C4 C 0.3920(5) 0.5764(5) 0.3461(3) 0.0288(16) Uani 1 1 d . . . . .
H4A H 0.3759 0.5067 0.3499 0.035 Uiso 1 1 calc R . . . .
H4B H 0.4529 0.5816 0.3597 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3462(6) 0.6363(6) 0.3975(4) 0.042(2) Uani 1 1 d . . . . .
H5A H 0.2874 0.6421 0.3785 0.063 Uiso 1 1 calc GR . . . .
H5B H 0.3713 0.7018 0.4023 0.063 Uiso 1 1 calc GR . . . .
H5C H 0.3499 0.6044 0.4456 0.063 Uiso 1 1 calc GR . . . .
C6 C 0.3865(4) 0.6007(4) 0.1376(3) 0.0203(13) Uani 1 1 d . . . . .
H6A H 0.3893 0.6731 0.1405 0.024 Uiso 1 1 calc R . . . .
H6B H 0.3269 0.5824 0.1280 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4326(5) 0.5674(5) 0.0731(3) 0.0235(14) Uani 1 1 d . . . . .
H7A H 0.4352 0.4950 0.0717 0.028 Uiso 1 1 calc R . . . .
H7B H 0.4904 0.5933 0.0780 0.028 Uiso 1 1 calc R . . . .
C8 C 0.3856(5) 0.6059(5) 0.0029(4) 0.0300(16) Uani 1 1 d . . . . .
H8A H 0.4168 0.5896 -0.0389 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.3797 0.6773 0.0062 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.3300 0.5757 -0.0036 0.045 Uiso 1 1 calc GR . . . .
C9 C 0.5124(4) 0.5738(4) 0.2267(3) 0.0180(12) Uani 1 1 d . . . . .
H9A H 0.5406 0.5458 0.1857 0.022 Uiso 1 1 calc R . . . .
H9B H 0.5319 0.5367 0.2714 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5394(4) 0.6805(4) 0.2371(4) 0.0255(15) Uani 1 1 d . . . . .
H10A H 0.5097 0.7217 0.1987 0.031 Uiso 1 1 calc R . . . .
H10B H 0.5250 0.7044 0.2853 0.031 Uiso 1 1 calc R . . . .
C11 C 0.6328(5) 0.6882(5) 0.2327(5) 0.0337(18) Uani 1 1 d . . . . .
H11A H 0.6477 0.6570 0.1876 0.051 Uiso 1 1 calc GR . . . .
H11B H 0.6622 0.6551 0.2750 0.051 Uiso 1 1 calc GR . . . .
H11C H 0.6492 0.7574 0.2328 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.4053(5) 0.4474(4) 0.2149(4) 0.0231(14) Uani 1 1 d . . . . .
H12A H 0.4350 0.4158 0.1762 0.028 Uiso 1 1 calc R . . . .
H12B H 0.4310 0.4233 0.2627 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3149(5) 0.4153(5) 0.2060(5) 0.0359(19) Uani 1 1 d . . . . .
H13A H 0.2903 0.4292 0.1556 0.043 Uiso 1 1 calc R . . . .
H13B H 0.2824 0.4515 0.2407 0.043 Uiso 1 1 calc R . . . .
C14 C 0.3114(6) 0.3050(5) 0.2214(4) 0.0369(19) Uani 1 1 d . . . . .
H14A H 0.3396 0.2693 0.1843 0.055 Uiso 1 1 calc GR . . . .
H14B H 0.2530 0.2838 0.2196 0.055 Uiso 1 1 calc GR . . . .
H14C H 0.3395 0.2913 0.2700 0.055 Uiso 1 1 calc GR . . . .
N4 N 0.6100(4) 0.0521(3) 0.3134(3) 0.0191(11) Uani 1 1 d . . . . .
C15 C 0.5175(4) 0.0239(4) 0.3074(4) 0.0230(14) Uani 1 1 d . . . . .
H15A H 0.5056 -0.0180 0.2636 0.028 Uiso 1 1 calc R . . . .
H15B H 0.5068 -0.0158 0.3507 0.028 Uiso 1 1 calc R . . . .
C16 C 0.4576(5) 0.1094(5) 0.3021(4) 0.0282(15) Uani 1 1 d . . . . .
H16A H 0.4533 0.1365 0.2518 0.034 Uiso 1 1 calc R . . . .
H16B H 0.4786 0.1618 0.3363 0.034 Uiso 1 1 calc R . . . .
C17 C 0.3724(5) 0.0752(5) 0.3209(5) 0.0381(19) Uani 1 1 d . . . . .
H17A H 0.3562 0.0163 0.2925 0.057 Uiso 1 1 calc GR . . . .
H17B H 0.3312 0.1271 0.3091 0.057 Uiso 1 1 calc GR . . . .
H17C H 0.3748 0.0602 0.3733 0.057 Uiso 1 1 calc GR . . . .
C18 C 0.6284(4) 0.1143(4) 0.2470(3) 0.0198(13) Uani 1 1 d . . . . .
H18A H 0.5933 0.1740 0.2458 0.024 Uiso 1 1 calc R . . . .
H18B H 0.6877 0.1353 0.2533 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6125(5) 0.0612(5) 0.1736(4) 0.0261(15) Uani 1 1 d . . . . .
H19A H 0.6488 0.0026 0.1732 0.031 Uiso 1 1 calc R . . . .
H19B H 0.5535 0.0392 0.1667 0.031 Uiso 1 1 calc R . . . .
C20 C 0.6304(5) 0.1293(5) 0.1117(4) 0.0319(17) Uani 1 1 d . . . . .
H20A H 0.6189 0.0953 0.0649 0.048 Uiso 1 1 calc GR . . . .
H20B H 0.6893 0.1493 0.1178 0.048 Uiso 1 1 calc GR . . . .
H20C H 0.5947 0.1875 0.1126 0.048 Uiso 1 1 calc GR . . . .
C21 C 0.6601(5) -0.0436(4) 0.3153(4) 0.0252(15) Uani 1 1 d . . . . .
H21A H 0.6479 -0.0806 0.3595 0.030 Uiso 1 1 calc R . . . .
H21B H 0.6393 -0.0833 0.2723 0.030 Uiso 1 1 calc R . . . .
C22 C 0.7526(5) -0.0348(4) 0.3156(4) 0.0271(15) Uani 1 1 d . . . . .
H22A H 0.7745 0.0079 0.3566 0.033 Uiso 1 1 calc R . . . .
H22B H 0.7666 -0.0044 0.2693 0.033 Uiso 1 1 calc R . . . .
C23 C 0.7935(5) -0.1362(4) 0.3240(4) 0.0250(14) Uani 1 1 d . . . . .
H23A H 0.7756 -0.1765 0.2812 0.037 Uiso 1 1 calc GR . . . .
H23B H 0.7767 -0.1679 0.3683 0.037 Uiso 1 1 calc GR . . . .
H23C H 0.8545 -0.1290 0.3279 0.037 Uiso 1 1 calc GR . . . .
C24 C 0.6333(5) 0.1141(4) 0.3805(3) 0.0214(14) Uani 1 1 d . . . . .
H24A H 0.6949 0.1214 0.3867 0.026 Uiso 1 1 calc R . . . .
H24B H 0.6090 0.1803 0.3722 0.026 Uiso 1 1 calc R . . . .
C25 C 0.6045(6) 0.0735(5) 0.4507(4) 0.037(2) Uani 1 1 d . . . . .
H25A H 0.6211 0.0038 0.4562 0.045 Uiso 1 1 calc R . . . .
H25B H 0.5427 0.0773 0.4491 0.045 Uiso 1 1 calc R . . . .
C26 C 0.6438(7) 0.1326(6) 0.5152(4) 0.050(3) Uani 1 1 d . . . . .
H26A H 0.6339 0.2026 0.5060 0.075 Uiso 1 1 calc GR . . . .
H26B H 0.7042 0.1201 0.5213 0.075 Uiso 1 1 calc GR . . . .
H26C H 0.6188 0.1132 0.5597 0.075 Uiso 1 1 calc GR . . . .


_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 1.932(6) . ?
Br2 C1 1.931(6) . ?
Br3 C1 1.949(6) . ?
O1 N1 1.202(8) . ?
O2 N1 1.218(8) . ?
N1 C1 1.541(7) . ?
Br4 C2 1.922(6) . ?
Br5 C2 1.918(7) . ?
Br6 C2 1.957(7) . ?
O3 N2 1.210(8) . ?
O4 N2 1.221(8) . ?
N2 C2 1.548(8) . ?
N3 C3 1.518(8) . ?
N3 C6 1.515(8) . ?
N3 C9 1.510(8) . ?
N3 C12 1.541(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.492(10) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.522(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.525(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.524(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.513(10) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.512(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.532(9) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N4 C15 1.528(9) . ?
N4 C18 1.536(8) . ?
N4 C21 1.531(8) . ?
N4 C24 1.512(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(9) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.515(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.530(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.514(9) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.490(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.533(9) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.512(10) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.521(10) . ?
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
O1 N1 O2 124.0(6) . . ?
O1 N1 C1 118.8(5) . . ?
O2 N1 C1 117.2(5) . . ?
Br1 C1 Br3 110.4(3) . . ?
Br2 C1 Br1 110.2(3) . . ?
Br2 C1 Br3 111.0(3) . . ?
N1 C1 Br1 109.3(4) . . ?
N1 C1 Br2 110.4(4) . . ?
N1 C1 Br3 105.4(4) . . ?
O3 N2 O4 124.1(6) . . ?
O3 N2 C2 118.0(6) . . ?
O4 N2 C2 117.8(6) . . ?
Br4 C2 Br6 110.7(3) . . ?
Br5 C2 Br4 110.8(3) . . ?
Br5 C2 Br6 111.6(3) . . ?
N2 C2 Br4 110.3(4) . . ?
N2 C2 Br5 109.5(4) . . ?
N2 C2 Br6 103.7(4) . . ?
C3 N3 C12 110.5(5) . . ?
C6 N3 C3 106.1(5) . . ?
C6 N3 C12 111.7(5) . . ?
C9 N3 C3 111.0(5) . . ?
C9 N3 C6 112.0(5) . . ?
C9 N3 C12 105.6(5) . . ?
N3 C3 H3A 108.5 . . ?
N3 C3 H3B 108.5 . . ?
N3 C3 C4 115.0(5) . . ?
H3A C3 H3B 107.5 . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.7(6) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 H6A 108.4 . . ?
N3 C6 H6B 108.4 . . ?
N3 C6 C7 115.3(5) . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C6 C7 C8 108.4(6) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
N3 C9 C10 114.6(5) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C9 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 109.3(5) . . ?
C11 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 108.5 . . ?
N3 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 N3 115.1(5) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C12 C13 C14 108.4(6) . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C15 N4 C18 109.8(5) . . ?
C15 N4 C21 107.0(5) . . ?
C21 N4 C18 110.4(5) . . ?
C24 N4 C15 111.5(5) . . ?
C24 N4 C18 106.6(4) . . ?
C24 N4 C21 111.6(5) . . ?
N4 C15 H15A 108.6 . . ?
N4 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 N4 114.8(5) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
C15 C16 C17 109.3(6) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N4 C18 H18A 108.7 . . ?
N4 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 N4 114.1(5) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 C18 110.0(5) . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 H21A 108.1 . . ?
N4 C21 H21B 108.1 . . ?
H21A C21 H21B 107.3 . . ?
C22 C21 N4 117.0(5) . . ?
C22 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C21 C22 H22A 109.6 . . ?
C21 C22 H22B 109.6 . . ?
C21 C22 C23 110.3(5) . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 H24A 108.6 . . ?
N4 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 N4 114.6(5) . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.8 . . ?
C24 C25 H25B 109.8 . . ?
C24 C25 C26 109.3(6) . . ?
H25A C25 H25B 108.3 . . ?
C26 C25 H25A 109.8 . . ?
C26 C25 H25B 109.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 Br1 135.8(6) . . . . ?
O1 N1 C1 Br2 14.4(8) . . . . ?
O1 N1 C1 Br3 -105.5(7) . . . . ?
O2 N1 C1 Br1 -46.1(7) . . . . ?
O2 N1 C1 Br2 -167.6(5) . . . . ?
O2 N1 C1 Br3 72.5(6) . . . . ?
O3 N2 C2 Br4 155.9(6) . . . . ?
O3 N2 C2 Br5 33.7(8) . . . . ?
O3 N2 C2 Br6 -85.6(7) . . . . ?
O4 N2 C2 Br4 -29.0(8) . . . . ?
O4 N2 C2 Br5 -151.1(6) . . . . ?
O4 N2 C2 Br6 89.6(7) . . . . ?
N3 C3 C4 C5 176.6(6) . . . . ?
N3 C6 C7 C8 173.3(5) . . . . ?
N3 C9 C10 C11 -165.6(6) . . . . ?
N3 C12 C13 C14 -172.4(6) . . . . ?
C3 N3 C6 C7 173.1(5) . . . . ?
C3 N3 C9 C10 -51.5(7) . . . . ?
C3 N3 C12 C13 56.0(7) . . . . ?
C6 N3 C3 C4 176.9(6) . . . . ?
C6 N3 C9 C10 66.9(7) . . . . ?
C6 N3 C12 C13 -61.9(8) . . . . ?
C9 N3 C3 C4 -61.2(7) . . . . ?
C9 N3 C6 C7 51.8(7) . . . . ?
C9 N3 C12 C13 176.1(6) . . . . ?
C12 N3 C3 C4 55.6(7) . . . . ?
C12 N3 C6 C7 -66.5(7) . . . . ?
C12 N3 C9 C10 -171.3(5) . . . . ?
N4 C15 C16 C17 -161.9(6) . . . . ?
N4 C18 C19 C20 178.6(6) . . . . ?
N4 C21 C22 C23 175.3(5) . . . . ?
N4 C24 C25 C26 170.6(7) . . . . ?
C15 N4 C18 C19 -61.9(7) . . . . ?
C15 N4 C21 C22 175.6(6) . . . . ?
C15 N4 C24 C25 49.1(8) . . . . ?
C18 N4 C15 C16 -58.1(7) . . . . ?
C18 N4 C21 C22 56.2(7) . . . . ?
C18 N4 C24 C25 168.9(6) . . . . ?
C21 N4 C15 C16 -177.9(6) . . . . ?
C21 N4 C18 C19 55.8(7) . . . . ?
C21 N4 C24 C25 -70.4(8) . . . . ?
C24 N4 C15 C16 59.8(7) . . . . ?
C24 N4 C18 C19 177.2(6) . . . . ?
C24 N4 C21 C22 -62.2(7) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_n3382
_database_code_depnum_ccdc_archive 'CCDC 1026791'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'I, C Br3 F, C12 H28 N'
_chemical_formula_sum            'C13 H28 Br3 F I N'
_chemical_formula_weight         583.99
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'
I I -0.4742 1.8119 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_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'

_cell_length_a                   33.76(3)
_cell_length_b                   8.427(6)
_cell_length_c                   14.421(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4102(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.534
_cell_measurement_theta_min      2.809
_shelx_estimated_absorpt_T_max   0.378
_shelx_estimated_absorpt_T_min   0.300
_exptl_absorpt_coefficient_mu    7.405
_exptl_absorpt_correction_T_max  0.7044
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1184 before and 0.1022 after correction.
The Ratio of minimum to maximum transmission is 0.9056.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       columnar
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.163
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            121246
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.066
_diffrn_reflns_theta_min         2.413
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                10976
_reflns_number_total             11920
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 
;
 Flack x determined using 4925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.041(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         11920
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0150P)²+3.5229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0578
_refine_ls_wR_factor_ref         0.0596
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
  C25(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C),
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
I2 I 0.55323(2) 0.75714(4) 0.50050(2) 0.02266(7) Uani 1 1 d . . . . .
I1 I 0.70492(2) 0.21832(4) 0.29039(2) 0.01932(7) Uani 1 1 d . . . . .
Br1 Br 0.37365(2) 0.00362(8) 0.42101(4) 0.03486(14) Uani 1 1 d . . . . .
Br2 Br 0.31949(2) 0.00152(7) 0.60357(3) 0.02189(11) Uani 1 1 d . . . . .
Br3 Br 0.28491(2) 0.14017(7) 0.41329(3) 0.02226(11) Uani 1 1 d . . . . .
F1 F 0.34626(11) 0.2602(4) 0.5105(3) 0.0376(8) Uani 1 1 d . . . . .
C1 C 0.33226(15) 0.1139(7) 0.4892(4) 0.0236(11) Uani 1 1 d . . . . .
Br4 Br 0.54727(2) 0.43867(6) 0.65547(3) 0.02000(10) Uani 1 1 d . . . . .
Br5 Br 0.51849(2) 0.24635(6) 0.83561(3) 0.02225(11) Uani 1 1 d . . . . .
Br6 Br 0.55649(2) 0.06102(7) 0.66187(3) 0.02340(11) Uani 1 1 d . . . . .
F2 F 0.59373(9) 0.2725(4) 0.7727(2) 0.0304(8) Uani 1 1 d . . . . .
C2 C 0.55696(14) 0.2566(6) 0.7345(4) 0.0190(10) Uani 1 1 d . . . . .
N1 N 0.70789(11) 0.8647(5) 0.5511(3) 0.0185(8) Uani 1 1 d . . . . .
C3 C 0.68274(14) 0.8410(7) 0.4633(3) 0.0208(10) Uani 1 1 d . . . . .
H3A H 0.6544 0.8435 0.4812 0.025 Uiso 1 1 calc R . . . .
H3B H 0.6875 0.9318 0.4212 0.025 Uiso 1 1 calc R . . . .
C4 C 0.69048(15) 0.6877(7) 0.4097(4) 0.0233(10) Uani 1 1 d . . . . .
H4A H 0.6864 0.5948 0.4506 0.028 Uiso 1 1 calc R . . . .
H4B H 0.7181 0.6858 0.3869 0.028 Uiso 1 1 calc R . . . .
C5 C 0.66158(17) 0.6812(8) 0.3276(4) 0.0303(12) Uani 1 1 d . . . . .
H5A H 0.6659 0.7732 0.2873 0.045 Uiso 1 1 calc GR . . . .
H5B H 0.6343 0.6827 0.3508 0.045 Uiso 1 1 calc GR . . . .
H5C H 0.6660 0.5835 0.2923 0.045 Uiso 1 1 calc GR . . . .
C6 C 0.69379(15) 0.7524(7) 0.6281(4) 0.0216(11) Uani 1 1 d . . . . .
H6A H 0.6939 0.6430 0.6031 0.026 Uiso 1 1 calc R . . . .
H6B H 0.7135 0.7559 0.6790 0.026 Uiso 1 1 calc R . . . .
C7 C 0.65301(16) 0.7842(7) 0.6696(4) 0.0265(12) Uani 1 1 d . . . . .
H7A H 0.6533 0.8865 0.7034 0.032 Uiso 1 1 calc R . . . .
H7B H 0.6330 0.7913 0.6195 0.032 Uiso 1 1 calc R . . . .
C8 C 0.64231(17) 0.6510(8) 0.7353(4) 0.0318(13) Uani 1 1 d . . . . .
H8A H 0.6408 0.5509 0.7009 0.048 Uiso 1 1 calc GR . . . .
H8B H 0.6166 0.6733 0.7640 0.048 Uiso 1 1 calc GR . . . .
H8C H 0.6626 0.6425 0.7837 0.048 Uiso 1 1 calc GR . . . .
C9 C 0.70282(15) 1.0374(7) 0.5799(3) 0.0230(11) Uani 1 1 d . . . . .
H9A H 0.7102 1.1054 0.5266 0.028 Uiso 1 1 calc R . . . .
H9B H 0.6744 1.0561 0.5929 0.028 Uiso 1 1 calc R . . . .
C10 C 0.72645(18) 1.0903(8) 0.6632(4) 0.0321(13) Uani 1 1 d . . . . .
H10A H 0.7551 1.0770 0.6507 0.039 Uiso 1 1 calc R . . . .
H10B H 0.7195 1.0242 0.7175 0.039 Uiso 1 1 calc R . . . .
C11 C 0.7176(2) 1.2630(8) 0.6838(5) 0.0405(16) Uani 1 1 d . . . . .
H11A H 0.7225 1.3269 0.6282 0.061 Uiso 1 1 calc GR . . . .
H11B H 0.7347 1.2999 0.7343 0.061 Uiso 1 1 calc GR . . . .
H11C H 0.6898 1.2740 0.7023 0.061 Uiso 1 1 calc GR . . . .
C12 C 0.75107(14) 0.8250(6) 0.5333(3) 0.0205(10) Uani 1 1 d . . . . .
H12A H 0.7528 0.7132 0.5126 0.025 Uiso 1 1 calc R . . . .
H12B H 0.7657 0.8336 0.5926 0.025 Uiso 1 1 calc R . . . .
C13 C 0.77152(15) 0.9290(7) 0.4618(4) 0.0275(12) Uani 1 1 d . . . . .
H13A H 0.7557 0.9314 0.4040 0.033 Uiso 1 1 calc R . . . .
H13B H 0.7737 1.0389 0.4856 0.033 Uiso 1 1 calc R . . . .
C14 C 0.81237(17) 0.8637(9) 0.4419(5) 0.0424(17) Uani 1 1 d . . . . .
H14A H 0.8100 0.7584 0.4136 0.064 Uiso 1 1 calc GR . . . .
H14B H 0.8273 0.8553 0.4999 0.064 Uiso 1 1 calc GR . . . .
H14C H 0.8263 0.9350 0.3992 0.064 Uiso 1 1 calc GR . . . .
N2 N 0.56399(10) 0.2038(5) 0.2886(3) 0.0154(7) Uani 1 1 d . . . . .
C15 C 0.58368(15) 0.0441(7) 0.2654(3) 0.0245(11) Uani 1 1 d . . . . .
H15A H 0.6119 0.0635 0.2506 0.029 Uiso 1 1 calc R . . . .
H15B H 0.5827 -0.0243 0.3212 0.029 Uiso 1 1 calc R . . . .
C16 C 0.56489(17) -0.0445(7) 0.1853(4) 0.0285(12) Uani 1 1 d . . . . .
H16A H 0.5728 0.0059 0.1261 0.034 Uiso 1 1 calc R . . . .
H16B H 0.5357 -0.0384 0.1905 0.034 Uiso 1 1 calc R . . . .
C17 C 0.57777(16) -0.2175(7) 0.1852(4) 0.0250(11) Uani 1 1 d . . . . .
H17A H 0.5647 -0.2734 0.1341 0.037 Uiso 1 1 calc GR . . . .
H17B H 0.5703 -0.2669 0.2442 0.037 Uiso 1 1 calc GR . . . .
H17C H 0.6066 -0.2235 0.1773 0.037 Uiso 1 1 calc GR . . . .
C18 C 0.59180(15) 0.2993(8) 0.3505(4) 0.0267(11) Uani 1 1 d . . . . .
H18A H 0.6175 0.3113 0.3180 0.032 Uiso 1 1 calc R . . . .
H18B H 0.5805 0.4069 0.3586 0.032 Uiso 1 1 calc R . . . .
C19 C 0.59972(19) 0.2299(8) 0.4460(4) 0.0316(13) Uani 1 1 d . . . . .
H19A H 0.6113 0.1226 0.4395 0.038 Uiso 1 1 calc R . . . .
H19B H 0.5745 0.2200 0.4804 0.038 Uiso 1 1 calc R . . . .
C20 C 0.62807(14) 0.3362(6) 0.4996(3) 0.0206(10) Uani 1 1 d . . . . .
H20A H 0.6544 0.3318 0.4709 0.031 Uiso 1 1 calc GR . . . .
H20B H 0.6298 0.2995 0.5639 0.031 Uiso 1 1 calc GR . . . .
H20C H 0.6183 0.4457 0.4984 0.031 Uiso 1 1 calc GR . . . .
C21 C 0.55621(16) 0.2988(8) 0.2008(4) 0.0264(11) Uani 1 1 d . . . . .
H21A H 0.5374 0.2384 0.1617 0.032 Uiso 1 1 calc R . . . .
H21B H 0.5431 0.3993 0.2185 0.032 Uiso 1 1 calc R . . . .
C22 C 0.59218(17) 0.3384(8) 0.1426(4) 0.0316(13) Uani 1 1 d . . . . .
H22A H 0.6075 0.4242 0.1728 0.038 Uiso 1 1 calc R . . . .
H22B H 0.6095 0.2440 0.1374 0.038 Uiso 1 1 calc R . . . .
C23 C 0.5792(2) 0.3911(8) 0.0472(4) 0.0343(14) Uani 1 1 d . . . . .
H23A H 0.6023 0.4266 0.0118 0.051 Uiso 1 1 calc GR . . . .
H23B H 0.5603 0.4788 0.0529 0.051 Uiso 1 1 calc GR . . . .
H23C H 0.5666 0.3021 0.0150 0.051 Uiso 1 1 calc GR . . . .
C24 C 0.52535(16) 0.1702(8) 0.3373(4) 0.0299(12) Uani 1 1 d . . . . .
H24A H 0.5080 0.1127 0.2933 0.036 Uiso 1 1 calc R . . . .
H24B H 0.5309 0.0970 0.3894 0.036 Uiso 1 1 calc R . . . .
C25 C 0.50253(17) 0.3072(9) 0.3748(4) 0.0380(15) Uani 1 1 d . . . . .
H25A H 0.4987 0.3870 0.3253 0.046 Uiso 1 1 calc R . . . .
H25B H 0.5178 0.3576 0.4255 0.046 Uiso 1 1 calc R . . . .
C26 C 0.4625(2) 0.2546(10) 0.4114(7) 0.058(2) Uani 1 1 d . . . . .
H26A H 0.4471 0.2069 0.3609 0.087 Uiso 1 1 calc GR . . . .
H26B H 0.4482 0.3467 0.4360 0.087 Uiso 1 1 calc GR . . . .
H26C H 0.4662 0.1764 0.4608 0.087 Uiso 1 1 calc GR . . . .


_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 1.945(6) . ?
Br2 C1 1.950(5) . ?
Br3 C1 1.950(5) . ?
F1 C1 1.355(6) . ?
Br4 C2 1.939(5) . ?
Br5 C2 1.955(5) . ?
Br6 C2 1.953(5) . ?
F2 C2 1.365(6) . ?
N1 C3 1.537(6) . ?
N1 C6 1.535(7) . ?
N1 C9 1.522(7) . ?
N1 C12 1.517(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.527(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.535(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.525(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.510(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.519(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N2 C15 1.537(7) . ?
N2 C18 1.526(6) . ?
N2 C21 1.521(7) . ?
N2 C24 1.508(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.515(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.521(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.519(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(8) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.513(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.511(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.490(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.518(9) . ?
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
Br1 C1 Br2 110.7(3) . . ?
Br1 C1 Br3 111.0(3) . . ?
Br3 C1 Br2 110.4(3) . . ?
F1 C1 Br1 107.4(4) . . ?
F1 C1 Br2 109.1(4) . . ?
F1 C1 Br3 108.1(3) . . ?
Br4 C2 Br5 111.2(2) . . ?
Br4 C2 Br6 110.6(3) . . ?
Br6 C2 Br5 111.0(2) . . ?
F2 C2 Br4 108.3(3) . . ?
F2 C2 Br5 107.9(3) . . ?
F2 C2 Br6 107.9(3) . . ?
C6 N1 C3 110.1(4) . . ?
C9 N1 C3 106.7(4) . . ?
C9 N1 C6 110.9(4) . . ?
C12 N1 C3 111.3(4) . . ?
C12 N1 C6 106.5(4) . . ?
C12 N1 C9 111.4(4) . . ?
N1 C3 H3A 108.4 . . ?
N1 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 N1 115.6(4) . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
C3 C4 C5 108.2(4) . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 108.0 . . ?
N1 C6 H6B 108.0 . . ?
H6A C6 H6B 107.3 . . ?
C7 C6 N1 117.1(4) . . ?
C7 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 C6 109.3(5) . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 108.3 . . ?
N1 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 N1 116.1(4) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C9 C10 C11 109.6(5) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 108.5 . . ?
N1 C12 H12B 108.5 . . ?
N1 C12 C13 115.1(4) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 C12 109.5(5) . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C18 N2 C15 108.8(4) . . ?
C21 N2 C15 110.8(4) . . ?
C21 N2 C18 108.4(4) . . ?
C24 N2 C15 108.1(4) . . ?
C24 N2 C18 111.0(4) . . ?
C24 N2 C21 109.7(4) . . ?
N2 C15 H15A 108.6 . . ?
N2 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 N2 114.6(4) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 C17 110.7(5) . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 H18A 108.3 . . ?
N2 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C19 C18 N2 115.8(5) . . ?
C19 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C18 C19 C20 110.1(5) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 108.3 . . ?
N2 C21 H21B 108.3 . . ?
H21A C21 H21B 107.4 . . ?
C22 C21 N2 116.1(4) . . ?
C22 C21 H21A 108.3 . . ?
C22 C21 H21B 108.3 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 C21 109.7(5) . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 107.8 . . ?
N2 C24 H24B 107.8 . . ?
H24A C24 H24B 107.1 . . ?
C25 C24 N2 118.1(5) . . ?
C25 C24 H24A 107.8 . . ?
C25 C24 H24B 107.8 . . ?
C24 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
C24 C25 C26 111.1(6) . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 177.4(4) . . . . ?
N1 C6 C7 C8 173.2(5) . . . . ?
N1 C9 C10 C11 -178.9(5) . . . . ?
N1 C12 C13 C14 -172.7(5) . . . . ?
C3 N1 C6 C7 -68.3(6) . . . . ?
C3 N1 C9 C10 -177.5(4) . . . . ?
C3 N1 C12 C13 62.7(6) . . . . ?
C6 N1 C3 C4 -72.8(5) . . . . ?
C6 N1 C9 C10 62.5(6) . . . . ?
C6 N1 C12 C13 -177.2(5) . . . . ?
C9 N1 C3 C4 166.8(4) . . . . ?
C9 N1 C6 C7 49.6(5) . . . . ?
C9 N1 C12 C13 -56.2(6) . . . . ?
C12 N1 C3 C4 45.1(6) . . . . ?
C12 N1 C6 C7 170.9(4) . . . . ?
C12 N1 C9 C10 -55.9(6) . . . . ?
N2 C15 C16 C17 -163.4(4) . . . . ?
N2 C18 C19 C20 179.5(4) . . . . ?
N2 C21 C22 C23 164.5(5) . . . . ?
N2 C24 C25 C26 173.4(6) . . . . ?
C15 N2 C18 C19 -65.2(6) . . . . ?
C15 N2 C21 C22 -59.2(6) . . . . ?
C15 N2 C24 C25 174.3(5) . . . . ?
C18 N2 C15 C16 -164.7(4) . . . . ?
C18 N2 C21 C22 60.1(6) . . . . ?
C18 N2 C24 C25 55.0(6) . . . . ?
C21 N2 C15 C16 -45.6(6) . . . . ?
C21 N2 C18 C19 174.2(5) . . . . ?
C21 N2 C24 C25 -64.8(6) . . . . ?
C24 N2 C15 C16 74.7(5) . . . . ?
C24 N2 C18 C19 53.6(6) . . . . ?
C24 N2 C21 C22 -178.5(5) . . . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
####################################################################### 
# 
# 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_n3535
_database_code_depnum_ccdc_archive 'CCDC 1026792'
_audit_update_record             
;
2014-09-28 deposited with the CCDC.
2015-01-16 downloaded from the CCDC.
;
_audit_creation_date             2014-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H28 N, C2 Br3 N, I'
_chemical_formula_sum            'C14 H28 Br3 I N2'
_chemical_formula_weight         591.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5118(3)
_cell_length_b                   18.3083(7)
_cell_length_c                   13.3813(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.315(2)
_cell_angle_gamma                90
_cell_volume                     2068.32(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6372
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.067
_cell_measurement_theta_min      4.114
_shelx_estimated_absorpt_T_max   0.765
_shelx_estimated_absorpt_T_min   0.137
_exptl_absorpt_coefficient_mu    18.899
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0658 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.6838.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.015
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.934
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12105
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.065
_diffrn_reflns_theta_min         4.114
_diffrn_ambient_temperature      100.04
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   microsource
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3278
_reflns_number_total             3484
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0621
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B), C13(H13A,H13B)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I1 I 0.29081(2) 0.84096(2) 0.12277(2) 0.01900(8) Uani 1 1 d . . . . .
Br1 Br 1.00191(4) 0.86175(2) 0.26927(2) 0.02111(10) Uani 1 1 d . . . . .
Br2 Br 0.62597(4) 0.86717(2) 0.27399(2) 0.02126(10) Uani 1 1 d . . . . .
Br3 Br 0.85159(4) 0.80994(2) 0.46688(2) 0.02196(10) Uani 1 1 d . . . . .
N1 N 0.8525(4) 1.01330(19) 0.4144(2) 0.0335(7) Uani 1 1 d . . . . .
C1 C 0.8456(4) 0.9546(2) 0.3905(2) 0.0220(7) Uani 1 1 d . . . . .
C2 C 0.8340(4) 0.87923(19) 0.3546(2) 0.0206(7) Uani 1 1 d . . . . .
N2 N 0.3542(3) 0.63130(15) 0.3506(2) 0.0184(6) Uani 1 1 d . . . . .
C3 C 0.5266(4) 0.62276(19) 0.3330(2) 0.0207(7) Uani 1 1 d . . . . .
H3A H 0.5945 0.6384 0.3949 0.025 Uiso 1 1 calc R . . . .
H3B H 0.5473 0.5702 0.3232 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5777(4) 0.6642(2) 0.2450(3) 0.0266(8) Uani 1 1 d . . . . .
H4A H 0.5447 0.7159 0.2475 0.032 Uiso 1 1 calc R . . . .
H4B H 0.5276 0.6428 0.1808 0.032 Uiso 1 1 calc R . . . .
C5 C 0.7574(5) 0.6593(2) 0.2512(3) 0.0354(10) Uani 1 1 d . . . . .
H5A H 0.7929 0.6865 0.1952 0.053 Uiso 1 1 calc GR . . . .
H5B H 0.7889 0.6080 0.2472 0.053 Uiso 1 1 calc GR . . . .
H5C H 0.8059 0.6802 0.3152 0.053 Uiso 1 1 calc GR . . . .
C6 C 0.3153(4) 0.71021(17) 0.3761(2) 0.0184(7) Uani 1 1 d . . . . .
H6A H 0.3320 0.7414 0.3179 0.022 Uiso 1 1 calc R . . . .
H6B H 0.2015 0.7129 0.3842 0.022 Uiso 1 1 calc R . . . .
C7 C 0.4095(4) 0.74183(19) 0.4694(2) 0.0235(7) Uani 1 1 d . . . . .
H7A H 0.5238 0.7418 0.4620 0.028 Uiso 1 1 calc R . . . .
H7B H 0.3938 0.7120 0.5290 0.028 Uiso 1 1 calc R . . . .
C8 C 0.3530(5) 0.8196(2) 0.4831(3) 0.0292(8) Uani 1 1 d . . . . .
H8A H 0.3693 0.8488 0.4239 0.044 Uiso 1 1 calc GR . . . .
H8B H 0.4131 0.8410 0.5433 0.044 Uiso 1 1 calc GR . . . .
H8C H 0.2401 0.8191 0.4908 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.3338(4) 0.58089(19) 0.4374(2) 0.0229(7) Uani 1 1 d . . . . .
H9A H 0.4200 0.5912 0.4925 0.028 Uiso 1 1 calc R . . . .
H9B H 0.3482 0.5301 0.4148 0.028 Uiso 1 1 calc R . . . .
C10 C 0.1778(4) 0.58482(19) 0.4806(3) 0.0254(8) Uani 1 1 d . . . . .
H10A H 0.0884 0.5769 0.4267 0.030 Uiso 1 1 calc R . . . .
H10B H 0.1651 0.6335 0.5108 0.030 Uiso 1 1 calc R . . . .
C11 C 0.1793(4) 0.52559(19) 0.5607(2) 0.0251(8) Uani 1 1 d . . . . .
H11A H 0.1797 0.4774 0.5288 0.038 Uiso 1 1 calc GR . . . .
H11B H 0.0848 0.5303 0.5951 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.2744 0.5309 0.6098 0.038 Uiso 1 1 calc GR . . . .
C12 C 0.2414(4) 0.61265(18) 0.2562(2) 0.0196(7) Uani 1 1 d . . . . .
H12A H 0.1315 0.6171 0.2724 0.023 Uiso 1 1 calc R . . . .
H12B H 0.2552 0.6496 0.2040 0.023 Uiso 1 1 calc R . . . .
C13 C 0.2603(4) 0.53753(19) 0.2114(3) 0.0272(8) Uani 1 1 d . . . . .
H13A H 0.2495 0.4995 0.2627 0.033 Uiso 1 1 calc R . . . .
H13B H 0.3669 0.5330 0.1898 0.033 Uiso 1 1 calc R . . . .
C14 C 0.1335(4) 0.5268(2) 0.1211(3) 0.0316(8) Uani 1 1 d . . . . .
H14A H 0.1434 0.5651 0.0712 0.047 Uiso 1 1 calc GR . . . .
H14B H 0.0284 0.5294 0.1434 0.047 Uiso 1 1 calc GR . . . .
H14C H 0.1474 0.4789 0.0907 0.047 Uiso 1 1 calc GR . . . .


_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 C2 1.965(3) . ?
Br2 C2 1.965(3) . ?
Br3 C2 1.958(3) . ?
N1 C1 1.120(5) . ?
C1 C2 1.461(5) . ?
N2 C3 1.524(4) . ?
N2 C6 1.530(4) . ?
N2 C9 1.510(4) . ?
N2 C12 1.526(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.511(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.523(5) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.511(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.521(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.516(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.517(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.527(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 C1 C2 177.3(4) . . ?
Br2 C2 Br1 109.52(15) . . ?
Br3 C2 Br1 110.50(17) . . ?
Br3 C2 Br2 108.90(15) . . ?
C1 C2 Br1 108.7(2) . . ?
C1 C2 Br2 107.8(2) . . ?
C1 C2 Br3 111.4(2) . . ?
C3 N2 C6 111.8(2) . . ?
C3 N2 C12 111.5(2) . . ?
C9 N2 C3 105.3(2) . . ?
C9 N2 C6 110.9(2) . . ?
C9 N2 C12 112.2(3) . . ?
C12 N2 C6 105.3(2) . . ?
N2 C3 H3A 108.1 . . ?
N2 C3 H3B 108.1 . . ?
H3A C3 H3B 107.3 . . ?
C4 C3 N2 116.6(3) . . ?
C4 C3 H3A 108.1 . . ?
C4 C3 H3B 108.1 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C3 C4 C5 108.3(3) . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 108.3 . . ?
N2 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C7 C6 N2 116.0(3) . . ?
C7 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
C6 C7 C8 108.4(3) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 H9A 108.0 . . ?
N2 C9 H9B 108.0 . . ?
N2 C9 C10 117.2(3) . . ?
H9A C9 H9B 107.2 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
C9 C10 C11 107.8(3) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 108.2 . . ?
N2 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 N2 116.3(3) . . ?
C13 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C12 C13 C14 109.2(3) . . ?
H13A C13 H13B 108.3 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C4 C5 170.3(3) . . . . ?
N2 C6 C7 C8 -179.2(3) . . . . ?
N2 C9 C10 C11 175.6(3) . . . . ?
N2 C12 C13 C14 177.2(3) . . . . ?
C3 N2 C6 C7 -60.1(3) . . . . ?
C3 N2 C9 C10 172.6(3) . . . . ?
C3 N2 C12 C13 55.8(4) . . . . ?
C6 N2 C3 C4 -63.1(4) . . . . ?
C6 N2 C9 C10 51.5(4) . . . . ?
C6 N2 C12 C13 177.2(3) . . . . ?
C9 N2 C3 C4 176.4(3) . . . . ?
C9 N2 C6 C7 57.1(3) . . . . ?
C9 N2 C12 C13 -62.0(3) . . . . ?
C12 N2 C3 C4 54.5(4) . . . . ?
C12 N2 C6 C7 178.7(3) . . . . ?
C12 N2 C9 C10 -66.0(4) . . . . ?

