# 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_ken272
_database_code_depnum_ccdc_archive 'CCDC 1407406'
_audit_update_record             
;
2015-06-23 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Br N3 O'
_chemical_formula_weight         412.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   14.356(4)
_cell_length_b                   8.145(2)
_cell_length_c                   16.636(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.488(4)
_cell_angle_gamma                90
_cell_volume                     1932.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  BrukerSMARTAPEXIICCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10840
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.777
_diffrn_reflns_theta_max         28.713
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4542
_reflns_number_gt                3665
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4542
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.204
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.71650(2) 0.30578(3) 0.10909(2) 0.03155(8) Uani 1 1 d . . . . .
C10 C 0.38223(12) 1.0592(2) 0.04481(10) 0.0198(4) Uani 1 1 d . . . . .
H10 H 0.4070 0.9703 0.0194 0.024 Uiso 1 1 calc R U . . .
C13 C 0.30997(13) 1.3129(2) 0.12296(11) 0.0222(4) Uani 1 1 d . . . . .
H13 H 0.2854 1.4004 0.1496 0.027 Uiso 1 1 calc R U . . .
C3 C 0.63959(13) 0.7528(2) 0.20398(11) 0.0209(4) Uani 1 1 d . . . . .
H3 H 0.6698 0.8495 0.2215 0.025 Uiso 1 1 calc R U . . .
C1 C 0.64790(13) 0.4803(2) 0.15110(10) 0.0224(4) Uani 1 1 d . . . . .
C8 C 0.33141(12) 0.8678(2) 0.15131(10) 0.0169(4) Uani 1 1 d . . . . .
H8 H 0.3536 0.7869 0.1143 0.020 Uiso 1 1 calc R U . . .
C16 C 0.07178(13) 0.8253(2) 0.08003(11) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.69179(12) 0.6236(2) 0.17813(10) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.7564 0.6338 0.1791 0.027 Uiso 1 1 calc R U . . .
C11 C 0.38533(13) 1.2149(2) 0.01221(11) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.4131 1.2324 -0.0350 0.028 Uiso 1 1 calc R U . . .
C15 C 0.17646(13) 0.8389(2) 0.07853(10) 0.0208(4) Uani 1 1 d . . . . .
H15A H 0.1970 0.7497 0.0462 0.025 Uiso 1 1 calc R U . . .
H15B H 0.1899 0.9410 0.0521 0.025 Uiso 1 1 calc R U . . .
C4 C 0.54193(13) 0.7402(2) 0.20420(10) 0.0189(4) Uani 1 1 d . . . . .
C9 C 0.34156(11) 1.0369(2) 0.11621(10) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.38930(12) 0.8498(2) 0.23397(11) 0.0196(4) Uani 1 1 d . . . . .
H7A H 0.3690 0.9317 0.2706 0.024 Uiso 1 1 calc R U . . .
H7B H 0.3777 0.7424 0.2560 0.024 Uiso 1 1 calc R U . . .
C6 C 0.55204(13) 0.4637(2) 0.15083(11) 0.0240(4) Uani 1 1 d . . . . .
H6 H 0.5227 0.3664 0.1330 0.029 Uiso 1 1 calc R U . . .
C5 C 0.49965(13) 0.5915(2) 0.17700(11) 0.0217(4) Uani 1 1 d . . . . .
H5 H 0.4352 0.5789 0.1766 0.026 Uiso 1 1 calc R U . . .
C20 C -0.07162(14) 0.9167(3) 0.12829(12) 0.0335(5) Uani 1 1 d . . . . .
H20 H -0.1019 0.9804 0.1638 0.040 Uiso 1 1 calc R U . . .
C12 C 0.34663(13) 1.3443(2) 0.05073(11) 0.0238(4) Uani 1 1 d . . . . .
H12 H 0.3452 1.4495 0.0289 0.029 Uiso 1 1 calc R U . . .
C19 C -0.12316(14) 0.8200(3) 0.07175(13) 0.0328(5) Uani 1 1 d . . . . .
H19 H -0.1883 0.8193 0.0686 0.039 Uiso 1 1 calc R U . . .
C14 C 0.53510(14) 1.0185(2) 0.26038(12) 0.0287(5) Uani 1 1 d . . . . .
H14A H 0.5774 0.9939 0.3078 0.043 Uiso 1 1 calc R U . . .
H14B H 0.4887 1.0953 0.2740 0.043 Uiso 1 1 calc R U . . .
H14C H 0.5695 1.0654 0.2198 0.043 Uiso 1 1 calc R U . . .
C18 C -0.07810(15) 0.7245(3) 0.01995(14) 0.0388(6) Uani 1 1 d . . . . .
H18 H -0.1128 0.6585 -0.0180 0.047 Uiso 1 1 calc R U . . .
C17 C 0.01937(15) 0.7264(3) 0.02431(13) 0.0325(5) Uani 1 1 d . . . . .
H17 H 0.0495 0.6608 -0.0105 0.039 Uiso 1 1 calc R U . . .
C21 C 0.02588(13) 0.9195(2) 0.13245(11) 0.0285(4) Uani 1 1 d . . . . .
H21 H 0.0603 0.9851 0.1708 0.034 Uiso 1 1 calc R U . . .
N1 N 0.30817(10) 1.16363(17) 0.15616(9) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.48946(10) 0.86874(19) 0.22955(9) 0.0222(3) Uani 1 1 d . . . . .
N3 N 0.23104(10) 0.83440(17) 0.15886(9) 0.0163(3) Uani 1 1 d . . . . .
O1 O 0.22769(9) 0.66262(14) 0.18214(7) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.2210 0.6561 0.2303 0.032 Uiso 1 1 calc R U . . .


_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 C1 1.9066(18) . ?
C10 C11 1.382(2) . ?
C10 C9 1.393(2) . ?
C13 N1 1.337(2) . ?
C13 C12 1.389(2) . ?
C3 C2 1.388(3) . ?
C3 C4 1.406(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.382(3) . ?
C8 N3 1.486(2) . ?
C8 C9 1.510(2) . ?
C8 C7 1.531(2) . ?
C16 C21 1.383(3) . ?
C16 C17 1.384(3) . ?
C16 C15 1.510(2) . ?
C11 C12 1.382(3) . ?
C15 N3 1.471(2) . ?
C4 N2 1.383(2) . ?
C4 C5 1.406(3) . ?
C9 N1 1.345(2) . ?
C7 N2 1.456(2) . ?
C6 C5 1.383(2) . ?
C20 C19 1.377(3) . ?
C20 C21 1.394(3) . ?
C19 C18 1.376(3) . ?
C14 N2 1.451(2) . ?
C18 C17 1.393(3) . ?
N3 O1 1.4540(17) . ?

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
C11 C10 C9 119.29(16) . . ?
N1 C13 C12 123.50(17) . . ?
C2 C3 C4 121.25(18) . . ?
C2 C1 C6 120.17(17) . . ?
C2 C1 Br1 121.01(14) . . ?
C6 C1 Br1 118.76(14) . . ?
N3 C8 C9 109.67(14) . . ?
N3 C8 C7 109.87(13) . . ?
C9 C8 C7 111.61(14) . . ?
C21 C16 C17 118.89(18) . . ?
C21 C16 C15 121.05(17) . . ?
C17 C16 C15 119.89(17) . . ?
C1 C2 C3 120.03(17) . . ?
C12 C11 C10 119.03(17) . . ?
N3 C15 C16 114.33(14) . . ?
N2 C4 C5 121.32(16) . . ?
N2 C4 C3 121.53(17) . . ?
C5 C4 C3 117.15(16) . . ?
N1 C9 C10 121.90(16) . . ?
N1 C9 C8 116.98(14) . . ?
C10 C9 C8 121.11(15) . . ?
N2 C7 C8 112.54(14) . . ?
C5 C6 C1 120.12(17) . . ?
C6 C5 C4 121.28(17) . . ?
C19 C20 C21 120.15(19) . . ?
C11 C12 C13 118.17(17) . . ?
C18 C19 C20 119.8(2) . . ?
C19 C18 C17 120.1(2) . . ?
C16 C17 C18 120.6(2) . . ?
C16 C21 C20 120.49(19) . . ?
C13 N1 C9 117.97(15) . . ?
C4 N2 C14 120.30(15) . . ?
C4 N2 C7 120.66(15) . . ?
C14 N2 C7 118.71(14) . . ?
O1 N3 C15 103.64(12) . . ?
O1 N3 C8 105.08(12) . . ?
C15 N3 C8 109.92(13) . . ?

_refine_diff_density_max         0.446
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.058

