# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1502070'
_audit_update_record             
;
2016-09-01 deposited with the CCDC.
2017-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br N O'
_chemical_formula_weight         122.94

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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.8738(4)
_cell_length_b                   16.4725(5)
_cell_length_c                   7.3033(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.2548(16)
_cell_angle_gamma                90
_cell_volume                     1610.26(8)
_cell_formula_units_Z            20
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.536
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.500
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22334
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2854
_reflns_number_gt                2552
_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 (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)+(0.1000P)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         2854
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_restrained_S_all      0.697
_refine_ls_shift/su_max          0.003
_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_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 0.11629(2) 1.19577(2) 0.40169(3) 0.01929(11) Uani 1 1 d . . . . .
C5 C 0.40217(17) 1.19214(12) 0.3348(3) 0.0232(5) Uani 1 1 d . . . . .
H5 H 0.4466 1.2307 0.3120 0.028 Uiso 1 1 calc R U . . .
C1 C 0.24468(13) 1.15772(11) 0.3888(2) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.36396(13) 1.05431(11) 0.3899(2) 0.0141(4) Uani 1 1 d . . . . .
H3 H 0.3831 1.0000 0.4017 0.017 Uiso 1 1 calc R U . . .
C2 C 0.26958(13) 1.07594(11) 0.4124(2) 0.0122(4) Uani 1 1 d . . . . .
C4 C 0.42884(14) 1.11085(12) 0.3512(2) 0.0179(4) Uani 1 1 d . . . . .
H4 H 0.4905 1.0946 0.3360 0.022 Uiso 1 1 calc R U . . .
O1 O 0.17218(9) 0.96512(7) 0.27655(16) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.20084(13) 1.01132(10) 0.4515(2) 0.0118(4) Uani 1 1 d . . . . .
H6 H 0.1410 1.0379 0.4707 0.014 Uiso 1 1 calc R U . . .
C8 C 0.24338(13) 0.95445(10) 0.6217(2) 0.0130(4) Uani 1 1 d . . . . .
H8 H 0.3017 0.9269 0.5987 0.016 Uiso 1 1 calc R U . . .
C10 C 0.09064(14) 0.91045(11) 0.2739(3) 0.0164(4) Uani 1 1 d . . . . .
H10 H 0.0356 0.9416 0.3004 0.020 Uiso 1 1 calc R U . . .
C7 C 0.16359(14) 0.88898(12) 0.6223(3) 0.0173(4) Uani 1 1 d . . . . .
H7A H 0.1920 0.8483 0.7171 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1078 0.9140 0.6578 0.021 Uiso 1 1 calc R U . . .
C9 C 0.12545(14) 0.84770(12) 0.4297(3) 0.0181(4) Uani 1 1 d . . . . .
H9A H 0.1784 0.8151 0.4030 0.022 Uiso 1 1 calc R U . . .
H9B H 0.0704 0.8119 0.4327 0.022 Uiso 1 1 calc R U . . .
C11 C 0.05624(15) 0.87603(12) 0.0762(3) 0.0230(4) Uani 1 1 d . . . . .
H11A H 0.0383 0.9196 -0.0136 0.035 Uiso 1 1 calc R U . . .
H11B H -0.0007 0.8417 0.0674 0.035 Uiso 1 1 calc R U . . .
H11C H 0.1092 0.8448 0.0489 0.035 Uiso 1 1 calc R U . . .
C12 C 0.27858(13) 0.99916(11) 0.8183(2) 0.0141(4) Uani 1 1 d . . . . .
C13 C 0.19925(14) 1.05770(11) 0.8527(3) 0.0172(4) Uani 1 1 d . . . . .
H13A H 0.1385 1.0285 0.8453 0.026 Uiso 1 1 calc R U . . .
H13B H 0.1870 1.0996 0.7581 0.026 Uiso 1 1 calc R U . . .
H13C H 0.2226 1.0816 0.9764 0.026 Uiso 1 1 calc R U . . .
C14 C 0.37674(14) 1.04540(11) 0.8424(3) 0.0160(4) Uani 1 1 d . . . . .
H14A H 0.3998 1.0644 0.9708 0.024 Uiso 1 1 calc R U . . .
H14B H 0.3661 1.0909 0.7572 0.024 Uiso 1 1 calc R U . . .
H14C H 0.4259 1.0099 0.8145 0.024 Uiso 1 1 calc R U . . .
N1 N 0.29369(11) 0.93877(9) 0.9744(2) 0.0135(3) Uani 1 1 d . . . . .
H1 H 0.2585 0.9445 1.0544 0.016 Uiso 1 1 calc R U . . .
C15 C 0.35785(13) 0.87582(11) 1.0014(2) 0.0152(4) Uani 1 1 d . . . . .
O2 O 0.40625(9) 0.85695(8) 0.88876(18) 0.0194(3) Uani 1 1 d . . . . .
C16 C 0.36712(16) 0.82830(13) 1.1825(3) 0.0213(4) Uani 1 1 d . . . . .
H16A H 0.3599 0.7714 1.1537 0.032 Uiso 1 1 calc R U . . .
H16B H 0.3158 0.8452 1.2405 0.032 Uiso 1 1 calc R U . . .
H16C H 0.4315 0.8382 1.2682 0.032 Uiso 1 1 calc R U . . .
C17 C 0.30965(15) 1.21595(12) 0.3523(3) 0.0208(4) Uani 1 1 d . . . . .
H17 H 0.2910 1.2703 0.3398 0.025 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 1.9138(18) . ?
C5 C17 1.380(3) . ?
C5 C4 1.386(3) . ?
C1 C17 1.389(3) . ?
C1 C2 1.390(2) . ?
C3 C4 1.375(3) . ?
C3 C2 1.408(2) . ?
C2 C6 1.506(2) . ?
O1 C10 1.442(2) . ?
O1 C6 1.450(2) . ?
C6 C8 1.545(2) . ?
C8 C7 1.546(2) . ?
C8 C12 1.572(2) . ?
C10 C11 1.507(2) . ?
C10 C9 1.519(3) . ?
C7 C9 1.527(3) . ?
C12 N1 1.486(2) . ?
C12 C14 1.530(2) . ?
C12 C13 1.533(2) . ?
N1 C15 1.347(2) . ?
C15 O2 1.231(2) . ?
C15 C16 1.513(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
C17 C5 C4 120.02(18) . . ?
C17 C1 C2 122.69(18) . . ?
C17 C1 Br1 116.27(14) . . ?
C2 C1 Br1 121.03(14) . . ?
C4 C3 C2 122.12(17) . . ?
C1 C2 C3 116.06(16) . . ?
C1 C2 C6 124.01(16) . . ?
C3 C2 C6 119.88(16) . . ?
C3 C4 C5 119.85(18) . . ?
C10 O1 C6 111.82(13) . . ?
O1 C6 C2 104.17(13) . . ?
O1 C6 C8 110.42(13) . . ?
C2 C6 C8 117.02(14) . . ?
C6 C8 C7 107.65(14) . . ?
C6 C8 C12 114.31(14) . . ?
C7 C8 C12 112.00(14) . . ?
O1 C10 C11 107.28(14) . . ?
O1 C10 C9 108.74(14) . . ?
C11 C10 C9 114.82(16) . . ?
C9 C7 C8 112.50(15) . . ?
C10 C9 C7 110.61(16) . . ?
N1 C12 C14 107.65(14) . . ?
N1 C12 C13 104.92(14) . . ?
C14 C12 C13 108.88(15) . . ?
N1 C12 C8 109.53(14) . . ?
C14 C12 C8 113.07(14) . . ?
C13 C12 C8 112.37(14) . . ?
C15 N1 C12 125.60(15) . . ?
O2 C15 N1 123.53(17) . . ?
O2 C15 C16 121.18(17) . . ?
N1 C15 C16 115.29(16) . . ?
C5 C17 C1 119.21(18) . . ?

_refine_diff_density_max         0.302
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

