# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_datam
_database_code_depnum_ccdc_archive 'CCDC 969501'
_audit_update_record             
;
2013-10-30 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 Br N O4'
_chemical_formula_sum            'C22 H20 Br N O4'
_chemical_formula_weight         442.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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/c'

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

_cell_length_a                   5.414(6)
_cell_length_b                   20.283(19)
_cell_length_c                   18.171(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.881(19)
_cell_angle_gamma                90.00
_cell_volume                     1993(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    3231
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    2.091
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.5728
_exptl_absorpt_correction_T_max  0.6799
_exptl_absorpt_process_details   'Busing and Levy (1957) Acta Cryst. 10, 180'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      301(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  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14461
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         26.50
_reflns_number_total             4011
_reflns_number_gt                3044
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1377P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4011
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.2142
_refine_ls_wR_factor_gt          0.1854
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 1.2666(7) 0.19245(18) 0.5563(2) 0.0488(8) Uani 1 1 d . . .
C3 C 1.0911(6) 0.25333(16) 0.54675(18) 0.0450(7) Uani 1 1 d . . .
C4 C 0.9370(6) 0.24842(16) 0.61251(18) 0.0440(7) Uani 1 1 d . . .
C5 C 1.0024(7) 0.19158(18) 0.6506(2) 0.0477(8) Uani 1 1 d . . .
C6 C 0.8896(9) 0.17397(18) 0.7152(3) 0.0602(10) Uani 1 1 d . . .
H6 H 0.9341 0.1357 0.7407 0.072 Uiso 1 1 calc R . .
C7 C 0.7095(8) 0.2156(2) 0.7398(2) 0.0605(10) Uani 1 1 d . . .
H7 H 0.6285 0.2049 0.7821 0.073 Uiso 1 1 calc R . .
C8 C 0.6486(7) 0.27287(19) 0.70230(19) 0.0510(8) Uani 1 1 d . . .
C9 C 0.7598(6) 0.29003(16) 0.63800(18) 0.0447(7) Uani 1 1 d . . .
H9 H 0.7159 0.3285 0.6128 0.054 Uiso 1 1 calc R . .
C11 C 1.2826(7) 0.33411(15) 0.47966(19) 0.0438(8) Uani 1 1 d . . .
C12 C 1.1449(8) 0.2931(2) 0.4236(2) 0.0580(10) Uani 1 1 d . . .
H12B H 1.2555 0.2634 0.3994 0.070 Uiso 1 1 calc R . .
H12A H 1.0592 0.3204 0.3867 0.070 Uiso 1 1 calc R . .
C13 C 0.9616(7) 0.25477(18) 0.4684(2) 0.0503(8) Uani 1 1 d . . .
H13B H 0.9364 0.2105 0.4492 0.060 Uiso 1 1 calc R . .
H13A H 0.8034 0.2772 0.4687 0.060 Uiso 1 1 calc R . .
C14 C 1.4330(7) 0.38625(18) 0.4733(2) 0.0514(8) Uani 1 1 d . . .
H14 H 1.4939 0.4068 0.5161 0.062 Uiso 1 1 calc R . .
C15 C 1.5059(8) 0.41229(17) 0.4030(2) 0.0541(9) Uani 1 1 d . . .
C16 C 1.7797(13) 0.4897(3) 0.3507(3) 0.0967(19) Uani 1 1 d . . .
H16B H 1.6556 0.5146 0.3222 0.116 Uiso 1 1 calc R . .
H16A H 1.8434 0.4555 0.3195 0.116 Uiso 1 1 calc R . .
C17 C 1.9846(12) 0.5342(3) 0.3778(3) 0.0903(17) Uani 1 1 d . . .
H17B H 2.0619 0.5534 0.3365 0.135 Uiso 1 1 calc R . .
H17A H 2.1047 0.5092 0.4068 0.135 Uiso 1 1 calc R . .
H16C H 1.9190 0.5685 0.4075 0.135 Uiso 1 1 calc R . .
C18 C 1.3039(7) 0.09697(18) 0.6423(2) 0.0581(10) Uani 1 1 d . . .
H18A H 1.3508 0.1017 0.6943 0.070 Uiso 1 1 calc R . .
H18B H 1.4537 0.0893 0.6164 0.070 Uiso 1 1 calc R . .
C19 C 1.1373(7) 0.03744(17) 0.6323(2) 0.0478(8) Uani 1 1 d . . .
C20 C 1.1966(9) -0.0204(2) 0.6693(3) 0.0713(12) Uani 1 1 d . . .
H20 H 1.3376 -0.0215 0.7007 0.086 Uiso 1 1 calc R . .
C21 C 1.0545(10) -0.0767(2) 0.6613(3) 0.0788(14) Uani 1 1 d . . .
H21 H 1.0989 -0.1145 0.6877 0.095 Uiso 1 1 calc R . .
C22 C 0.8497(9) -0.0769(2) 0.6149(2) 0.0656(11) Uani 1 1 d . . .
H22 H 0.7549 -0.1149 0.6086 0.079 Uiso 1 1 calc R . .
C23 C 0.7848(9) -0.0203(2) 0.5775(3) 0.0659(11) Uani 1 1 d . . .
H23 H 0.6437 -0.0201 0.5461 0.079 Uiso 1 1 calc R . .
C24 C 0.9258(8) 0.0365(2) 0.5857(2) 0.0586(9) Uani 1 1 d . . .
H24 H 0.8784 0.0743 0.5597 0.070 Uiso 1 1 calc R . .
N1 N 1.1922(6) 0.15827(15) 0.61581(19) 0.0523(7) Uani 1 1 d . . .
O2 O 1.4346(6) 0.17847(14) 0.51719(19) 0.0628(8) Uani 1 1 d . . .
O3 O 1.2374(5) 0.31349(12) 0.54911(12) 0.0464(6) Uani 1 1 d . . .
O15 O 1.4347(7) 0.39437(17) 0.34215(17) 0.0794(10) Uani 1 1 d . . .
O16 O 1.6730(7) 0.46075(15) 0.41398(16) 0.0745(9) Uani 1 1 d . . .
Br8 Br 0.40591(9) 0.32905(2) 0.74056(3) 0.0706(3) 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
C2 O2 1.216(5) . ?
C2 N1 1.362(5) . ?
C2 C3 1.563(5) . ?
C3 O3 1.454(4) . ?
C3 C4 1.495(5) . ?
C3 C13 1.555(5) . ?
C4 C9 1.375(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.396(6) . ?
C5 N1 1.406(5) . ?
C6 C7 1.381(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(5) . ?
C8 Br8 1.897(4) . ?
C9 H9 0.9300 . ?
C11 C14 1.343(5) . ?
C11 O3 1.363(4) . ?
C11 C12 1.487(5) . ?
C12 C13 1.527(5) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13A 0.9700 . ?
C14 C15 1.455(5) . ?
C14 H14 0.9300 . ?
C15 O15 1.208(5) . ?
C15 O16 1.344(5) . ?
C16 O16 1.437(5) . ?
C16 C17 1.494(8) . ?
C16 H16B 0.9700 . ?
C16 H16A 0.9700 . ?
C17 H17B 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H16C 0.9600 . ?
C18 N1 1.454(5) . ?
C18 C19 1.513(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.383(5) . ?
C19 C24 1.390(5) . ?
C20 C21 1.379(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.358(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(6) . ?
C23 H23 0.9300 . ?
C24 H24 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
O2 C2 N1 127.2(4) . . ?
O2 C2 C3 126.0(3) . . ?
N1 C2 C3 106.7(3) . . ?
O3 C3 C4 110.9(3) . . ?
O3 C3 C13 103.4(3) . . ?
C4 C3 C13 119.3(3) . . ?
O3 C3 C2 109.4(3) . . ?
C4 C3 C2 102.7(3) . . ?
C13 C3 C2 111.1(3) . . ?
C9 C4 C5 120.6(3) . . ?
C9 C4 C3 130.9(3) . . ?
C5 C4 C3 108.5(3) . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 N1 110.5(3) . . ?
C6 C5 N1 128.0(4) . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.7(4) . . ?
C7 C8 Br8 118.6(3) . . ?
C9 C8 Br8 119.8(3) . . ?
C4 C9 C8 118.0(3) . . ?
C4 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
C14 C11 O3 117.4(3) . . ?
C14 C11 C12 131.8(3) . . ?
O3 C11 C12 110.8(3) . . ?
C11 C12 C13 103.7(3) . . ?
C11 C12 H12B 111.0 . . ?
C13 C12 H12B 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C13 C12 H12A 111.0 . . ?
H12B C12 H12A 109.0 . . ?
C12 C13 C3 102.9(3) . . ?
C12 C13 H13B 111.2 . . ?
C3 C13 H13B 111.2 . . ?
C12 C13 H13A 111.2 . . ?
C3 C13 H13A 111.2 . . ?
H13B C13 H13A 109.1 . . ?
C11 C14 C15 123.7(4) . . ?
C11 C14 H14 118.2 . . ?
C15 C14 H14 118.2 . . ?
O15 C15 O16 122.5(3) . . ?
O15 C15 C14 127.3(4) . . ?
O16 C15 C14 110.2(3) . . ?
O16 C16 C17 107.8(5) . . ?
O16 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
O16 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
H16B C16 H16A 108.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
C16 C17 H16C 109.5 . . ?
H17B C17 H16C 109.5 . . ?
H17A C17 H16C 109.5 . . ?
N1 C18 C19 114.0(3) . . ?
N1 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
N1 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 116.7(4) . . ?
C20 C19 C18 119.8(4) . . ?
C24 C19 C18 123.5(3) . . ?
C21 C20 C19 122.4(4) . . ?
C21 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.1(4) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 121.1(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C2 N1 C5 111.4(3) . . ?
C2 N1 C18 124.3(3) . . ?
C5 N1 C18 124.3(3) . . ?
C11 O3 C3 110.7(2) . . ?
C15 O16 C16 118.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.100
