# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_qqq
_database_code_depnum_ccdc_archive 'CCDC 1429220'
_audit_update_record             
;
2015-10-02 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Br4 N2'
_chemical_formula_weight         930.53

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'
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   'P 21/n'
_symmetry_space_group_name_Hall  'P 2yb '

loop_
_symmetry_equiv_pos_as_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                   8.3338(8)
_cell_length_b                   29.562(3)
_cell_length_c                   9.0991(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.598(3)
_cell_angle_gamma                90.00
_cell_volume                     2038.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    3.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4128
_exptl_absorpt_correction_T_max  0.4483
_exptl_absorpt_process_details   'SADABS (Sheldrick,2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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 Area Detector'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17559
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3582
_reflns_number_gt                2411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'APEX2 (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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)+(0.1923P)²+4.3405P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3582
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0869
_refine_ls_wR_factor_ref         0.3042
_refine_ls_wR_factor_gt          0.2720
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.008
_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
C1 C 0.5634(9) -0.0436(2) 0.5645(8) 0.0315(15) Uani 1 1 d . . .
C2 C 0.6308(10) -0.0868(2) 0.6334(9) 0.0384(17) Uani 1 1 d . . .
H2 H 0.5953 -0.1124 0.5684 0.046 Uiso 1 1 calc R . .
C3 C 0.7439(11) -0.0915(3) 0.7890(9) 0.0422(17) Uani 1 1 d . . .
H3 H 0.7822 -0.1201 0.8320 0.051 Uiso 1 1 calc R . .
C4 C 0.8051(10) -0.0521(3) 0.8882(9) 0.0418(17) Uani 1 1 d . . .
H4 H 0.8867 -0.0551 0.9950 0.050 Uiso 1 1 calc R . .
C5 C 0.7459(9) -0.0109(2) 0.8286(8) 0.0376(16) Uani 1 1 d . . .
H5 H 0.7889 0.0142 0.8952 0.045 Uiso 1 1 calc R . .
C6 C 0.6184(8) -0.0043(2) 0.6654(8) 0.0311(15) Uani 1 1 d . . .
C7 C 0.5545(9) 0.0386(2) 0.6019(8) 0.0312(15) Uani 1 1 d . . .
C8 C 0.6049(10) 0.0798(2) 0.7042(8) 0.0339(15) Uani 1 1 d . . .
H8 H 0.6504 0.1040 0.6680 0.041 Uiso 1 1 calc R . .
C9 C 0.5905(10) 0.0851(2) 0.8428(8) 0.0341(15) Uani 1 1 d . . .
H9 H 0.5458 0.0608 0.8792 0.041 Uiso 1 1 calc R . .
C10 C 0.6384(9) 0.1254(2) 0.9427(7) 0.0314(15) Uani 1 1 d . . .
C11 C 0.5859(10) 0.1310(2) 1.0684(8) 0.0388(17) Uani 1 1 d . . .
H11 H 0.5214 0.1082 1.0894 0.047 Uiso 1 1 calc R . .
C12 C 0.6270(10) 0.1691(2) 1.1616(8) 0.0386(17) Uani 1 1 d . . .
H12 H 0.5895 0.1722 1.2441 0.046 Uiso 1 1 calc R . .
C13 C 0.7359(10) 0.1603(2) 0.9184(8) 0.0390(17) Uani 1 1 d . . .
H13 H 0.7753 0.1578 0.8369 0.047 Uiso 1 1 calc R . .
C14 C 0.7752(11) 0.1983(2) 1.0127(9) 0.0420(18) Uani 1 1 d . . .
H14 H 0.8390 0.2216 0.9932 0.050 Uiso 1 1 calc R . .
C15 C 0.7648(11) 0.2446(2) 1.2313(8) 0.0398(17) Uani 1 1 d . . .
H15A H 0.8793 0.2557 1.2439 0.048 Uiso 1 1 calc R . .
H15B H 0.7709 0.2380 1.3380 0.048 Uiso 1 1 calc R . .
C16 C 0.6247(10) 0.2812(3) 1.1506(9) 0.0431(18) Uani 1 1 d . . .
H16A H 0.6192 0.2882 1.0444 0.052 Uiso 1 1 calc R . .
H16B H 0.5098 0.2702 1.1373 0.052 Uiso 1 1 calc R . .
C17 C 0.6710(12) 0.3235(3) 1.2540(10) 0.050(2) Uani 1 1 d . . .
H17A H 0.7867 0.3339 1.2675 0.060 Uiso 1 1 calc R . .
H17B H 0.6779 0.3159 1.3602 0.060 Uiso 1 1 calc R . .
C18 C 0.5385(12) 0.3621(3) 1.1835(10) 0.052(2) Uani 1 1 d . . .
H18A H 0.4206 0.3501 1.1533 0.063 Uiso 1 1 calc R . .
H18B H 0.5593 0.3844 1.2678 0.063 Uiso 1 1 calc R . .
C19 C 0.5432(11) 0.3856(3) 1.0403(10) 0.050(2) Uani 1 1 d . . .
H19A H 0.5260 0.3634 0.9565 0.060 Uiso 1 1 calc R . .
H19B H 0.6589 0.3990 1.0708 0.060 Uiso 1 1 calc R . .
C20 C 0.4031(11) 0.4225(3) 0.9716(9) 0.0460(19) Uani 1 1 d . . .
H20A H 0.2872 0.4087 0.9342 0.055 Uiso 1 1 calc R . .
H20B H 0.4149 0.4434 1.0577 0.055 Uiso 1 1 calc R . .
C21 C 0.4141(12) 0.4488(3) 0.8344(10) 0.052(2) Uani 1 1 d . . .
H21A H 0.4067 0.4279 0.7495 0.062 Uiso 1 1 calc R . .
H21B H 0.5277 0.4638 0.8725 0.062 Uiso 1 1 calc R . .
C22 C 0.2679(13) 0.4839(3) 0.7647(11) 0.061(2) Uani 1 1 d . . .
H22A H 0.2832 0.5006 0.6810 0.092 Uiso 1 1 calc R . .
H22B H 0.2730 0.5043 0.8487 0.092 Uiso 1 1 calc R . .
H22C H 0.1553 0.4690 0.7205 0.092 Uiso 1 1 calc R . .
N1 N 0.7224(8) 0.20250(17) 1.1337(6) 0.0318(13) Uani 1 1 d . . .
Br1 Br 1.1783(19) 0.2039(3) 1.222(2) 0.764(17) Uani 1 1 d . . .
Br2 Br 0.56768(12) 0.20415(3) 0.52373(10) 0.0577(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.429(10) . ?
C1 C7 1.429(9) 3_656 ?
C1 C6 1.434(9) . ?
C2 C3 1.342(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.430(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.435(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(9) . ?
C7 C1 1.429(9) 3_656 ?
C7 C8 1.485(9) . ?
C8 C9 1.325(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.450(9) . ?
C9 H9 0.9300 . ?
C10 C13 1.387(9) . ?
C10 C11 1.394(9) . ?
C11 C12 1.366(10) . ?
C11 H11 0.9300 . ?
C12 N1 1.356(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(9) . ?
C13 H13 0.9300 . ?
C14 N1 1.351(9) . ?
C14 H14 0.9300 . ?
C15 N1 1.483(8) . ?
C15 C16 1.536(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.516(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.532(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.491(11) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.530(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.504(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.525(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C2 C1 C7 122.0(6) . 3_656 ?
C2 C1 C6 118.7(6) . . ?
C7 C1 C6 119.3(6) 3_656 . ?
C3 C2 C1 122.0(7) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.4(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.7(7) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 122.1(7) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C1 120.2(6) . . ?
C7 C6 C5 122.7(6) . . ?
C1 C6 C5 117.0(6) . . ?
C6 C7 C1 120.5(6) . 3_656 ?
C6 C7 C8 121.6(6) . . ?
C1 C7 C8 118.0(6) 3_656 . ?
C9 C8 C7 125.4(6) . . ?
C9 C8 H8 117.3 . . ?
C7 C8 H8 117.3 . . ?
C8 C9 C10 125.6(6) . . ?
C8 C9 H9 117.2 . . ?
C10 C9 H9 117.2 . . ?
C13 C10 C11 116.6(6) . . ?
C13 C10 C9 122.5(6) . . ?
C11 C10 C9 120.9(6) . . ?
C12 C11 C10 121.6(6) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
N1 C12 C11 120.0(6) . . ?
N1 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C10 120.9(6) . . ?
C14 C13 H13 119.5 . . ?
C10 C13 H13 119.5 . . ?
N1 C14 C13 120.8(6) . . ?
N1 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
N1 C15 C16 111.1(6) . . ?
N1 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
N1 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C15 109.8(6) . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 113.7(7) . . ?
C16 C17 H17A 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 115.8(7) . . ?
C19 C18 H18A 108.3 . . ?
C17 C18 H18A 108.3 . . ?
C19 C18 H18B 108.3 . . ?
C17 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C18 C19 C20 113.3(6) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C19 114.0(6) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 C22 112.5(7) . . ?
C20 C21 H21A 109.1 . . ?
C22 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
C22 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
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 . . ?
C14 N1 C12 120.1(5) . . ?
C14 N1 C15 119.2(6) . . ?
C12 N1 C15 120.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.021
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.163
