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

####################################################################### 
# 
# 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_comp3g
_database_code_depnum_ccdc_archive 'CCDC 1009450'
_audit_update_record             
;
2014-06-20 deposited with the CCDC.
2014-12-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 Br N2 O4'
_chemical_formula_weight         461.35

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                   10.417(5)
_cell_length_b                   10.000(5)
_cell_length_c                   11.057(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.396(5)
_cell_angle_gamma                90.00
_cell_volume                     1105.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5594
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    1.889
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.689
_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9268
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.98
_reflns_number_total             4186
_reflns_number_gt                3558
_reflns_threshold_expression     >2σ(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 > 2σ(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)+(0.0859P)²+0.0000P] 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       0.056(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.060(11)
_refine_ls_number_reflns         4186
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Br Br 0.50565(4) 0.17846(10) 0.75099(4) 0.0625(2) Uani 1 1 d . . .
N1 N 0.8822(3) 0.1994(4) 0.1187(3) 0.0495(8) Uani 1 1 d . . .
N2 N 0.6959(3) 0.0034(3) 0.3064(3) 0.0361(6) Uani 1 1 d . . .
O2 O 1.0664(3) 0.1845(6) 0.0573(4) 0.0853(11) Uani 1 1 d . . .
O1 O 1.0597(4) 0.3403(5) 0.2025(4) 0.0898(12) Uani 1 1 d . . .
O3 O 0.7905(3) -0.1106(4) 0.1768(3) 0.0662(9) Uani 1 1 d . . .
O4 O 0.8510(3) -0.1504(3) 0.3860(3) 0.0554(8) Uani 1 1 d . . .
C1 C 1.0064(5) 0.2499(6) 0.1341(5) 0.0649(12) Uani 1 1 d . . .
C2 C 0.9833(6) 0.0747(8) 0.0010(7) 0.0831(16) Uani 1 1 d . . .
H2A H 1.0149 -0.0075 0.0462 0.100 Uiso 1 1 calc R . .
H2B H 0.9829 0.0637 -0.0863 0.100 Uiso 1 1 calc R . .
C3 C 0.8464(5) 0.1091(5) 0.0097(5) 0.0602(11) Uani 1 1 d . . .
H3A H 0.7935 0.1540 -0.0657 0.072 Uiso 1 1 calc R . .
H3B H 0.7987 0.0307 0.0256 0.072 Uiso 1 1 calc R . .
C4 C 0.7891(4) 0.2716(4) 0.1642(4) 0.0501(10) Uani 1 1 d . . .
H4 H 0.8055 0.3627 0.1769 0.060 Uiso 1 1 calc R . .
C5 C 0.6821(4) 0.2256(4) 0.1909(4) 0.0445(9) Uani 1 1 d . . .
C6 C 0.5787(5) 0.3022(4) 0.2370(5) 0.0619(13) Uani 1 1 d . . .
H6A H 0.6174 0.3565 0.3111 0.074 Uiso 1 1 calc R . .
H6B H 0.5174 0.3543 0.1717 0.074 Uiso 1 1 calc R . .
C7 C 0.5202(3) 0.1719(8) 0.2659(3) 0.0475(9) Uani 1 1 d . . .
C8 C 0.5615(3) 0.1268(4) 0.3995(4) 0.0407(9) Uani 1 1 d . . .
C9 C 0.5141(3) 0.1681(4) 0.4974(4) 0.0456(9) Uani 1 1 d . . .
H9 H 0.4455 0.2307 0.4838 0.055 Uiso 1 1 calc R . .
C10 C 0.5692(4) 0.1158(4) 0.6157(4) 0.0442(8) Uani 1 1 d . . .
C11 C 0.6684(3) 0.0204(4) 0.6367(4) 0.0408(8) Uani 1 1 d . . .
H11 H 0.7028 -0.0150 0.7171 0.049 Uiso 1 1 calc R . .
C12 C 0.7174(3) -0.0233(3) 0.5400(3) 0.0378(8) Uani 1 1 d . . .
H12 H 0.7849 -0.0873 0.5547 0.045 Uiso 1 1 calc R . .
C13 C 0.6640(3) 0.0300(3) 0.4205(3) 0.0347(7) Uani 1 1 d . . .
C14 C 0.6169(3) 0.0907(4) 0.2047(4) 0.0379(8) Uani 1 1 d . . .
C15 C 0.5272(4) 0.0230(5) 0.0867(4) 0.0526(10) Uani 1 1 d . . .
H15A H 0.5140 -0.0706 0.1028 0.063 Uiso 1 1 calc R . .
H15B H 0.5664 0.0294 0.0171 0.063 Uiso 1 1 calc R . .
C16 C 0.3944(3) 0.0996(5) 0.0571(4) 0.0827(18) Uani 1 1 d . . .
H16A H 0.3210 0.0440 0.0100 0.099 Uiso 1 1 calc R . .
H16B H 0.3981 0.1795 0.0085 0.099 Uiso 1 1 calc R . .
C17 C 0.3771(3) 0.1360(5) 0.1869(4) 0.0726(16) Uani 1 1 d R . .
H17A H 0.3424 0.0608 0.2233 0.087 Uiso 1 1 d R . .
H17B H 0.3172 0.2115 0.1806 0.087 Uiso 1 1 d R . .
C18 C 0.7820(4) -0.0899(4) 0.2812(4) 0.0420(8) Uani 1 1 d . . .
C19 C 0.9542(5) -0.2523(5) 0.3848(5) 0.0617(12) Uani 1 1 d . . .
C20 C 0.8916(6) -0.3700(5) 0.3058(6) 0.0794(16) Uani 1 1 d . . .
H20A H 0.8108 -0.3947 0.3256 0.119 Uiso 1 1 calc R . .
H20B H 0.9529 -0.4439 0.3230 0.119 Uiso 1 1 calc R . .
H20C H 0.8711 -0.3467 0.2182 0.119 Uiso 1 1 calc R . .
C21 C 1.0024(10) -0.2891(10) 0.5218(6) 0.129(4) Uani 1 1 d . . .
H21A H 1.0459 -0.2134 0.5696 0.194 Uiso 1 1 calc R . .
H21B H 1.0646 -0.3620 0.5326 0.194 Uiso 1 1 calc R . .
H21C H 0.9276 -0.3154 0.5510 0.194 Uiso 1 1 calc R . .
C22 C 1.0618(6) -0.1896(8) 0.3336(9) 0.114(3) Uani 1 1 d . . .
H22A H 1.0254 -0.1719 0.2452 0.172 Uiso 1 1 calc R . .
H22B H 1.1360 -0.2500 0.3462 0.172 Uiso 1 1 calc R . .
H22C H 1.0917 -0.1073 0.3773 0.172 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br C10 1.904(4) . ?
N1 C1 1.355(6) . ?
N1 C4 1.410(5) . ?
N1 C3 1.468(6) . ?
N2 C18 1.375(4) . ?
N2 C13 1.418(5) . ?
N2 C14 1.477(4) . ?
O2 C1 1.356(7) . ?
O2 C2 1.428(8) . ?
O1 C1 1.209(7) . ?
O3 C18 1.201(5) . ?
O4 C18 1.325(5) . ?
O4 C19 1.483(4) . ?
C2 C3 1.496(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.314(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.522(6) . ?
C5 C14 1.537(5) . ?
C6 C7 1.511(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.488(6) . ?
C7 C17 1.542(5) . ?
C7 C14 1.587(6) . ?
C8 C9 1.373(6) . ?
C8 C13 1.411(5) . ?
C9 C10 1.375(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9300 . ?
C14 C15 1.532(6) . ?
C15 C16 1.534(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.5391 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 C21 1.501(8) . ?
C19 C20 1.501(7) . ?
C19 C22 1.526(9) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
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
C1 N1 C4 119.5(4) . . ?
C1 N1 C3 110.2(4) . . ?
C4 N1 C3 124.6(3) . . ?
C18 N2 C13 129.6(3) . . ?
C18 N2 C14 120.1(3) . . ?
C13 N2 C14 110.2(3) . . ?
C1 O2 C2 108.3(4) . . ?
C18 O4 C19 121.4(3) . . ?
O1 C1 N1 127.7(5) . . ?
O1 C1 O2 122.8(5) . . ?
N1 C1 O2 109.5(4) . . ?
O2 C2 C3 105.5(5) . . ?
O2 C2 H2A 110.6 . . ?
C3 C2 H2A 110.6 . . ?
O2 C2 H2B 110.6 . . ?
C3 C2 H2B 110.6 . . ?
H2A C2 H2B 108.8 . . ?
N1 C3 C2 99.7(4) . . ?
N1 C3 H3A 111.8 . . ?
C2 C3 H3A 111.8 . . ?
N1 C3 H3B 111.8 . . ?
C2 C3 H3B 111.8 . . ?
H3A C3 H3B 109.6 . . ?
C5 C4 N1 127.8(4) . . ?
C5 C4 H4 116.1 . . ?
N1 C4 H4 116.1 . . ?
C4 C5 C6 128.6(4) . . ?
C4 C5 C14 139.1(4) . . ?
C6 C5 C14 92.0(3) . . ?
C7 C6 C5 90.2(3) . . ?
C7 C6 H6A 113.6 . . ?
C5 C6 H6A 113.6 . . ?
C7 C6 H6B 113.6 . . ?
C5 C6 H6B 113.6 . . ?
H6A C6 H6B 110.9 . . ?
C8 C7 C6 116.8(5) . . ?
C8 C7 C17 117.1(4) . . ?
C6 C7 C17 117.7(4) . . ?
C8 C7 C14 103.2(4) . . ?
C6 C7 C14 90.4(3) . . ?
C17 C7 C14 105.6(4) . . ?
C9 C8 C13 120.0(4) . . ?
C9 C8 C7 128.6(4) . . ?
C13 C8 C7 111.4(4) . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 121.0(4) . . ?
C9 C10 Br 118.6(3) . . ?
C11 C10 Br 120.4(3) . . ?
C10 C11 C12 120.9(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 120.1(3) . . ?
C12 C13 N2 130.0(3) . . ?
C8 C13 N2 109.9(3) . . ?
N2 C14 C15 117.5(3) . . ?
N2 C14 C5 115.3(3) . . ?
C15 C14 C5 118.9(3) . . ?
N2 C14 C7 105.2(3) . . ?
C15 C14 C7 106.3(3) . . ?
C5 C14 C7 86.9(4) . . ?
C14 C15 C16 104.9(3) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.8 . . ?
C15 C16 C17 104.8(2) . . ?
C15 C16 H16A 110.8 . . ?
C17 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C17 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
C16 C17 C7 103.6(2) . . ?
C16 C17 H17A 111.0 . . ?
C7 C17 H17A 111.1 . . ?
C16 C17 H17B 111.0 . . ?
C7 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
O3 C18 O4 126.4(3) . . ?
O3 C18 N2 122.8(3) . . ?
O4 C18 N2 110.9(3) . . ?
O4 C19 C21 101.4(4) . . ?
O4 C19 C20 110.3(4) . . ?
C21 C19 C20 111.2(6) . . ?
O4 C19 C22 109.3(4) . . ?
C21 C19 C22 113.8(6) . . ?
C20 C19 C22 110.5(5) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.024
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.071
#===END
