# 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_jv_mk1342_1_vesely_org
_database_code_depnum_ccdc_archive 'CCDC 1038569'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-01-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Br N5 O'
_chemical_formula_sum            'C26 H22 Br N5 O'
_chemical_formula_weight         500.40
_chemical_compound_source        'synthesized by the authors'

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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'

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                   9.6625(2)
_cell_length_b                   23.9818(6)
_cell_length_c                   10.8059(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.7526(7)
_cell_angle_gamma                90.00
_cell_volume                     2255.29(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7712
_cell_measurement_theta_min      2.4896
_cell_measurement_theta_max      26.7124

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.852
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_T_max  0.7376
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29307
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.50
_reflns_number_total             5177
_reflns_number_gt                3951
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker Instrument Service v2012.12.0.0'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0527P)²+2.6400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5177
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 -0.05135(4) 0.058121(19) 0.32436(4) 0.05802(16) Uani 1 1 d . . .
C1 C 0.7369(3) 0.40664(10) 0.6344(2) 0.0172(5) Uani 1 1 d . . .
C2 C 0.7445(3) 0.34621(10) 0.5976(2) 0.0172(5) Uani 1 1 d . . .
C3 C 0.8972(3) 0.32933(10) 0.7172(2) 0.0193(5) Uani 1 1 d . . .
C4 C 1.0744(3) 0.38080(10) 0.9306(2) 0.0175(5) Uani 1 1 d . . .
C5 C 1.1477(3) 0.33397(11) 1.0063(2) 0.0204(5) Uani 1 1 d . . .
H5 H 1.1199 0.2977 0.9680 0.024 Uiso 1 1 calc R . .
C6 C 1.2626(3) 0.34093(12) 1.1393(3) 0.0248(6) Uani 1 1 d . . .
H6 H 1.3133 0.3092 1.1922 0.030 Uiso 1 1 calc R . .
C7 C 1.3032(3) 0.39351(13) 1.1948(3) 0.0307(6) Uani 1 1 d . . .
H7 H 1.3803 0.3979 1.2862 0.037 Uiso 1 1 calc R . .
C8 C 1.2318(3) 0.44007(12) 1.1173(3) 0.0338(7) Uani 1 1 d . . .
H8 H 1.2614 0.4763 1.1552 0.041 Uiso 1 1 calc R . .
C9 C 1.1172(3) 0.43392(11) 0.9845(3) 0.0253(6) Uani 1 1 d . . .
H9 H 1.0685 0.4658 0.9310 0.030 Uiso 1 1 calc R . .
C10 C 0.6102(3) 0.44603(11) 0.5559(3) 0.0217(5) Uani 1 1 d . . .
H10A H 0.6239 0.4805 0.6089 0.033 Uiso 1 1 calc R . .
H10B H 0.5115 0.4289 0.5394 0.033 Uiso 1 1 calc R . .
H10C H 0.6115 0.4547 0.4678 0.033 Uiso 1 1 calc R . .
C11 C 0.6130(3) 0.31426(10) 0.6039(2) 0.0185(5) Uani 1 1 d . . .
C12 C 0.6049(3) 0.28275(11) 0.7063(2) 0.0229(5) Uani 1 1 d . . .
H12 H 0.6857 0.2741 0.7936 0.027 Uiso 1 1 calc R . .
C13 C 0.3791(4) 0.23395(13) 0.7214(3) 0.0347(7) Uani 1 1 d . . .
H13A H 0.3188 0.2592 0.7518 0.042 Uiso 1 1 calc R . .
H13B H 0.4571 0.2152 0.8039 0.042 Uiso 1 1 calc R . .
C14 C 0.2739(3) 0.19082(11) 0.6257(3) 0.0256(6) Uani 1 1 d . . .
C15 C 0.1163(3) 0.19481(13) 0.5799(3) 0.0325(6) Uani 1 1 d . . .
H15 H 0.0743 0.2249 0.6097 0.039 Uiso 1 1 calc R . .
C16 C 0.0195(3) 0.15533(14) 0.4911(3) 0.0350(7) Uani 1 1 d . . .
H16 H -0.0885 0.1580 0.4602 0.042 Uiso 1 1 calc R . .
C17 C 0.0819(3) 0.11212(13) 0.4483(3) 0.0300(6) Uani 1 1 d . . .
C18 C 0.2378(3) 0.10677(12) 0.4935(3) 0.0280(6) Uani 1 1 d . . .
H18 H 0.2790 0.0765 0.4637 0.034 Uiso 1 1 calc R . .
C19 C 0.3336(3) 0.14605(12) 0.5829(3) 0.0264(6) Uani 1 1 d . . .
H19 H 0.4417 0.1425 0.6156 0.032 Uiso 1 1 calc R . .
C20 C 0.7498(3) 0.33776(11) 0.4577(2) 0.0216(5) Uani 1 1 d . . .
H20A H 0.7832 0.2991 0.4532 0.026 Uiso 1 1 calc R . .
H20B H 0.6447 0.3422 0.3833 0.026 Uiso 1 1 calc R . .
C21 C 0.8558(3) 0.37755(11) 0.4320(2) 0.0227(5) Uani 1 1 d . . .
C22 C 0.7971(3) 0.42283(13) 0.3439(3) 0.0291(6) Uani 1 1 d . . .
H22 H 0.6892 0.4287 0.2999 0.035 Uiso 1 1 calc R . .
C23 C 0.8931(4) 0.45954(14) 0.3192(3) 0.0367(7) Uani 1 1 d . . .
H23 H 0.8509 0.4906 0.2599 0.044 Uiso 1 1 calc R . .
C24 C 1.0492(4) 0.45100(14) 0.3805(4) 0.0412(8) Uani 1 1 d . . .
H24 H 1.1151 0.4760 0.3633 0.049 Uiso 1 1 calc R . .
C25 C 1.1100(4) 0.40610(15) 0.4670(3) 0.0411(8) Uani 1 1 d . . .
H25 H 1.2179 0.4001 0.5090 0.049 Uiso 1 1 calc R . .
C26 C 1.0143(3) 0.36946(13) 0.4932(3) 0.0302(6) Uani 1 1 d . . .
H26 H 1.0573 0.3387 0.5533 0.036 Uiso 1 1 calc R . .
N1 N 0.9482(2) 0.37513(9) 0.79904(19) 0.0177(4) Uani 1 1 d . . .
N2 N 0.8495(2) 0.42179(9) 0.7464(2) 0.0182(4) Uani 1 1 d . . .
N3 N 0.4568(3) 0.26682(10) 0.6553(2) 0.0252(5) Uani 1 1 d . . .
N4 N 0.3756(3) 0.28699(11) 0.5281(2) 0.0306(5) Uani 1 1 d . . .
N5 N 0.4714(2) 0.31618(10) 0.4966(2) 0.0279(5) Uani 1 1 d . . .
O1 O 0.9601(2) 0.28421(8) 0.73387(19) 0.0275(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
Br1 C17 1.905(3) . ?
C1 N2 1.279(3) . ?
C1 C10 1.486(3) . ?
C1 C2 1.513(3) . ?
C2 C11 1.510(3) . ?
C2 C3 1.534(3) . ?
C2 C20 1.548(3) . ?
C3 O1 1.216(3) . ?
C3 N1 1.361(3) . ?
C4 C9 1.387(4) . ?
C4 C5 1.389(3) . ?
C4 N1 1.421(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N5 1.357(3) . ?
C11 C12 1.370(3) . ?
C12 N3 1.346(3) . ?
C12 H12 0.9500 . ?
C13 N3 1.470(3) . ?
C13 C14 1.503(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.385(4) . ?
C14 C19 1.390(4) . ?
C15 C16 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(4) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.511(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.392(4) . ?
C21 C26 1.393(4) . ?
C22 C23 1.386(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.374(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 N2 1.419(3) . ?
N3 N4 1.342(3) . ?
N4 N5 1.317(3) . ?

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
N2 C1 C10 120.7(2) . . ?
N2 C1 C2 113.7(2) . . ?
C10 C1 C2 125.5(2) . . ?
C11 C2 C1 109.67(19) . . ?
C11 C2 C3 110.4(2) . . ?
C1 C2 C3 99.81(18) . . ?
C11 C2 C20 111.27(19) . . ?
C1 C2 C20 114.1(2) . . ?
C3 C2 C20 111.1(2) . . ?
O1 C3 N1 127.3(2) . . ?
O1 C3 C2 126.6(2) . . ?
N1 C3 C2 106.2(2) . . ?
C9 C4 C5 120.8(2) . . ?
C9 C4 N1 118.5(2) . . ?
C5 C4 N1 120.6(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 119.3(2) . . ?
C4 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 108.6(2) . . ?
N5 C11 C2 120.0(2) . . ?
C12 C11 C2 131.3(2) . . ?
N3 C12 C11 104.5(2) . . ?
N3 C12 H12 127.8 . . ?
C11 C12 H12 127.8 . . ?
N3 C13 C14 111.7(2) . . ?
N3 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N3 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C19 119.1(3) . . ?
C15 C14 C13 120.5(3) . . ?
C19 C14 C13 120.4(3) . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 Br1 119.2(2) . . ?
C16 C17 Br1 119.2(2) . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C21 C20 C2 114.2(2) . . ?
C21 C20 H20A 108.7 . . ?
C2 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C2 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C22 C21 C26 118.1(3) . . ?
C22 C21 C20 120.7(2) . . ?
C26 C21 C20 121.2(2) . . ?
C23 C22 C21 121.3(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C3 N1 N2 112.67(18) . . ?
C3 N1 C4 129.6(2) . . ?
N2 N1 C4 117.44(19) . . ?
C1 N2 N1 107.6(2) . . ?
N4 N3 C12 111.1(2) . . ?
N4 N3 C13 119.8(2) . . ?
C12 N3 C13 129.0(2) . . ?
N5 N4 N3 107.0(2) . . ?
N4 N5 C11 108.8(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.014
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.071
#===END
