# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_cd212185

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Br N O'
_chemical_formula_weight         398.33

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'
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   P2(1)

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

_cell_length_a                   8.705(2)
_cell_length_b                   9.823(3)
_cell_length_c                   11.361(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.490(6)
_cell_angle_gamma                90.00
_cell_volume                     963.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1230
_cell_measurement_theta_min      4.719
_cell_measurement_theta_max      39.923

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.231
_exptl_crystal_size_min          0.132
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.13408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5846
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2849
_reflns_number_gt                2064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0340P)²+0.0276P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(12)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.99449(7) 0.45368(13) 1.01296(4) 0.1329(4) Uani 1 1 d . . .
N1 N 0.6947(3) 0.5836(3) 0.4218(2) 0.0449(7) Uani 1 1 d . . .
O1 O 0.5093(3) 0.6519(3) 0.5298(2) 0.0700(9) Uani 1 1 d . . .
C1 C 0.5802(4) 0.5886(4) 0.3119(3) 0.0505(9) Uani 1 1 d . . .
H1 H 0.4848 0.5465 0.3318 0.061 Uiso 1 1 calc R . .
C2 C 0.5375(4) 0.7334(4) 0.2695(4) 0.0614(12) Uani 1 1 d . . .
H2 H 0.4950 0.7800 0.3343 0.074 Uiso 1 1 calc R . .
C3 C 0.4043(5) 0.7181(6) 0.1661(4) 0.0779(14) Uani 1 1 d . . .
H3A H 0.3126 0.6859 0.1977 0.093 Uiso 1 1 calc R . .
H3B H 0.3806 0.8070 0.1312 0.093 Uiso 1 1 calc R . .
C4 C 0.4403(5) 0.6212(6) 0.0694(4) 0.0813(15) Uani 1 1 d . . .
H4A H 0.3475 0.6081 0.0133 0.098 Uiso 1 1 calc R . .
H4B H 0.5185 0.6618 0.0270 0.098 Uiso 1 1 calc R . .
C5 C 0.4970(5) 0.4853(5) 0.1173(4) 0.0709(11) Uani 1 1 d . . .
H5A H 0.5274 0.4302 0.0534 0.085 Uiso 1 1 calc R . .
H5B H 0.4140 0.4385 0.1499 0.085 Uiso 1 1 calc R . .
C6 C 0.6343(4) 0.5024(4) 0.2132(3) 0.0563(10) Uani 1 1 d . . .
H6 H 0.7106 0.5575 0.1782 0.068 Uiso 1 1 calc R . .
C7 C 0.7189(5) 0.3770(4) 0.2638(4) 0.0580(10) Uani 1 1 d . . .
H7A H 0.6567 0.3268 0.3139 0.070 Uiso 1 1 calc R . .
H7B H 0.7439 0.3175 0.2008 0.070 Uiso 1 1 calc R . .
C8 C 0.8645(4) 0.4310(4) 0.3354(3) 0.0459(9) Uani 1 1 d . . .
C9 C 1.0126(5) 0.3880(4) 0.3219(3) 0.0575(10) Uani 1 1 d . . .
H9 H 1.0260 0.3154 0.2717 0.069 Uiso 1 1 calc R . .
C10 C 1.1401(4) 0.4518(6) 0.3821(3) 0.0660(11) Uani 1 1 d . . .
H10 H 1.2388 0.4189 0.3755 0.079 Uiso 1 1 calc R . .
C11 C 1.1231(4) 0.5633(5) 0.4517(4) 0.0606(11) Uani 1 1 d . . .
H11 H 1.2100 0.6073 0.4903 0.073 Uiso 1 1 calc R . .
C12 C 0.9761(4) 0.6104(4) 0.4643(3) 0.0502(9) Uani 1 1 d . . .
H12 H 0.9637 0.6873 0.5099 0.060 Uiso 1 1 calc R . .
C13 C 0.8487(4) 0.5423(4) 0.4089(3) 0.0441(9) Uani 1 1 d . . .
C14 C 0.6737(5) 0.8167(5) 0.2400(4) 0.0701(12) Uani 1 1 d . . .
H14A H 0.7626 0.7956 0.2978 0.084 Uiso 1 1 calc R . .
H14B H 0.6982 0.7879 0.1629 0.084 Uiso 1 1 calc R . .
C15 C 0.6524(5) 0.9668(5) 0.2373(4) 0.0821(12) Uani 1 1 d . . .
H15A H 0.5670 0.9900 0.1784 0.123 Uiso 1 1 calc R . .
H15B H 0.7450 1.0097 0.2179 0.123 Uiso 1 1 calc R . .
H15C H 0.6313 0.9977 0.3137 0.123 Uiso 1 1 calc R . .
C16 C 0.6400(4) 0.6038(4) 0.5270(3) 0.0501(9) Uani 1 1 d . . .
C17 C 0.7342(4) 0.5639(4) 0.6417(3) 0.0483(9) Uani 1 1 d . . .
C18 C 0.7171(4) 0.6418(4) 0.7410(3) 0.0568(11) Uani 1 1 d . . .
H18 H 0.6514 0.7168 0.7334 0.068 Uiso 1 1 calc R . .
C19 C 0.7952(5) 0.6101(6) 0.8504(4) 0.0708(13) Uani 1 1 d . . .
H19 H 0.7850 0.6640 0.9162 0.085 Uiso 1 1 calc R . .
C20 C 0.8890(5) 0.4965(6) 0.8603(3) 0.0759(16) Uani 1 1 d . . .
C21 C 0.9028(5) 0.4148(6) 0.7663(4) 0.0774(15) Uani 1 1 d . . .
H21 H 0.9637 0.3368 0.7759 0.093 Uiso 1 1 calc R . .
C22 C 0.8258(4) 0.4483(5) 0.6562(3) 0.0620(10) Uani 1 1 d . . .
H22 H 0.8355 0.3928 0.5912 0.074 Uiso 1 1 calc R . .


_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 C20 1.901(4) . ?
N1 C16 1.357(4) . ?
N1 C13 1.427(4) . ?
N1 C1 1.493(4) . ?
O1 C16 1.237(4) . ?
C1 C6 1.528(5) . ?
C1 C2 1.531(6) . ?
C1 H1 0.9800 . ?
C2 C14 1.514(6) . ?
C2 C3 1.547(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.517(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.501(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.518(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.510(6) . ?
C6 H6 0.9800 . ?
C7 C8 1.510(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.383(5) . ?
C8 C13 1.393(5) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C14 C15 1.486(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.498(5) . ?
C17 C22 1.385(6) . ?
C17 C18 1.388(5) . ?
C18 C19 1.372(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.353(7) . ?
C21 C22 1.381(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

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
C16 N1 C13 125.0(3) . . ?
C16 N1 C1 117.3(3) . . ?
C13 N1 C1 117.2(3) . . ?
N1 C1 C6 111.1(3) . . ?
N1 C1 C2 113.7(3) . . ?
C6 C1 C2 111.6(3) . . ?
N1 C1 H1 106.6 . . ?
C6 C1 H1 106.6 . . ?
C2 C1 H1 106.6 . . ?
C14 C2 C1 114.0(3) . . ?
C14 C2 C3 114.5(4) . . ?
C1 C2 C3 106.0(4) . . ?
C14 C2 H2 107.3 . . ?
C1 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
C4 C3 C2 113.9(3) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 112.6(4) . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 110.7(4) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 118.8(4) . . ?
C7 C6 C1 110.8(3) . . ?
C5 C6 C1 107.4(3) . . ?
C7 C6 H6 106.4 . . ?
C5 C6 H6 106.4 . . ?
C1 C6 H6 106.4 . . ?
C8 C7 C6 104.6(3) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C13 118.2(3) . . ?
C9 C8 C7 124.2(4) . . ?
C13 C8 C7 117.2(3) . . ?
C10 C9 C8 120.6(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C8 121.3(3) . . ?
C12 C13 N1 121.8(3) . . ?
C8 C13 N1 116.9(3) . . ?
C15 C14 C2 116.2(4) . . ?
C15 C14 H14A 108.2 . . ?
C2 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
C2 C14 H14B 108.2 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 N1 120.5(3) . . ?
O1 C16 C17 118.6(3) . . ?
N1 C16 C17 120.8(3) . . ?
C22 C17 C18 118.5(4) . . ?
C22 C17 C16 124.0(4) . . ?
C18 C17 C16 117.3(3) . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 118.4(4) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C21 C20 C19 121.9(4) . . ?
C21 C20 Br1 120.4(4) . . ?
C19 C20 Br1 117.7(4) . . ?
C20 C21 C22 119.4(5) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C21 C22 C17 120.5(4) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?

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
C16 N1 C1 C6 -153.1(3) . . . . ?
C13 N1 C1 C6 19.8(4) . . . . ?
C16 N1 C1 C2 80.0(4) . . . . ?
C13 N1 C1 C2 -107.2(3) . . . . ?
N1 C1 C2 C14 60.1(4) . . . . ?
C6 C1 C2 C14 -66.5(4) . . . . ?
N1 C1 C2 C3 -173.0(3) . . . . ?
C6 C1 C2 C3 60.4(4) . . . . ?
C14 C2 C3 C4 73.9(5) . . . . ?
C1 C2 C3 C4 -52.8(5) . . . . ?
C2 C3 C4 C5 51.6(6) . . . . ?
C3 C4 C5 C6 -54.0(5) . . . . ?
C4 C5 C6 C7 -173.7(4) . . . . ?
C4 C5 C6 C1 59.7(4) . . . . ?
N1 C1 C6 C7 35.3(4) . . . . ?
C2 C1 C6 C7 163.4(3) . . . . ?
N1 C1 C6 C5 166.6(3) . . . . ?
C2 C1 C6 C5 -65.4(4) . . . . ?
C5 C6 C7 C8 168.5(3) . . . . ?
C1 C6 C7 C8 -66.4(4) . . . . ?
C6 C7 C8 C9 -126.9(4) . . . . ?
C6 C7 C8 C13 45.0(4) . . . . ?
C13 C8 C9 C10 1.6(5) . . . . ?
C7 C8 C9 C10 173.4(4) . . . . ?
C8 C9 C10 C11 -3.4(6) . . . . ?
C9 C10 C11 C12 1.8(6) . . . . ?
C10 C11 C12 C13 1.5(6) . . . . ?
C11 C12 C13 C8 -3.3(5) . . . . ?
C11 C12 C13 N1 178.0(3) . . . . ?
C9 C8 C13 C12 1.7(5) . . . . ?
C7 C8 C13 C12 -170.7(3) . . . . ?
C9 C8 C13 N1 -179.5(3) . . . . ?
C7 C8 C13 N1 8.1(4) . . . . ?
C16 N1 C13 C12 -52.6(5) . . . . ?
C1 N1 C13 C12 135.2(3) . . . . ?
C16 N1 C13 C8 128.7(4) . . . . ?
C1 N1 C13 C8 -43.6(4) . . . . ?
C1 C2 C14 C15 -160.5(4) . . . . ?
C3 C2 C14 C15 77.1(5) . . . . ?
C13 N1 C16 O1 173.1(4) . . . . ?
C1 N1 C16 O1 -14.7(5) . . . . ?
C13 N1 C16 C17 -9.0(5) . . . . ?
C1 N1 C16 C17 163.2(3) . . . . ?
O1 C16 C17 C22 140.3(4) . . . . ?
N1 C16 C17 C22 -37.6(5) . . . . ?
O1 C16 C17 C18 -33.8(5) . . . . ?
N1 C16 C17 C18 148.3(3) . . . . ?
C22 C17 C18 C19 3.5(5) . . . . ?
C16 C17 C18 C19 178.0(3) . . . . ?
C17 C18 C19 C20 -1.6(5) . . . . ?
C18 C19 C20 C21 -1.5(6) . . . . ?
C18 C19 C20 Br1 -179.4(3) . . . . ?
C19 C20 C21 C22 2.5(7) . . . . ?
Br1 C20 C21 C22 -179.7(3) . . . . ?
C20 C21 C22 C17 -0.4(6) . . . . ?
C18 C17 C22 C21 -2.5(5) . . . . ?
C16 C17 C22 C21 -176.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 994490'
