# Electronic Supplementary Material (ESI) for ChemComm.
# 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 1527208'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-03-09 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            '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.7312(6)
_cell_length_b                   11.0728(6)
_cell_length_c                   12.9937(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1543.97(15)
_cell_formula_units_Z            19
_cell_measurement_temperature    273(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    2.512
_exptl_crystal_F_000             1083
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.385
_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      273(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            9239
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.417
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3168
_reflns_number_gt                2694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.996

_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.961(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     89
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1658
_refine_ls_R_factor_gt           0.1508
_refine_ls_wR_factor_ref         0.3885
_refine_ls_wR_factor_gt          0.3735
_refine_ls_goodness_of_fit_ref   2.748
_refine_ls_restrained_S_all      2.748
_refine_ls_shift/su_max          0.005
_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 0.1126(2) 0.2757(2) 0.46481(14) 0.0470(8) Uiso 1 1 d . . . . .
O1 O 0.9053(12) 0.5447(12) 0.6791(9) 0.034(3) Uiso 1 1 d . . . . .
C2 C 0.2460(16) 0.3747(18) 0.5136(12) 0.031(4) Uiso 1 1 d . . . . .
N1 N 0.6519(12) 0.7562(12) 0.6490(8) 0.024(3) Uiso 1 1 d . . . . .
O4 O 0.9138(13) 0.7476(13) 0.6977(9) 0.041(3) Uiso 1 1 d . . . . .
N2 N 0.5338(13) 0.5954(14) 0.6195(10) 0.029(3) Uiso 1 1 d . . . . .
C6 C 0.5375(14) 0.7203(17) 0.6281(11) 0.025(3) Uiso 1 1 d . . . . .
C7 C 0.4348(15) 0.5208(16) 0.5840(12) 0.023(3) Uiso 1 1 d . . . . .
C9 C 0.3470(18) 0.9955(19) 0.5729(14) 0.036(4) Uiso 1 1 d . . . . .
C10 C 0.3790(16) 0.5456(16) 0.4895(11) 0.029(3) Uiso 1 1 d . . . . .
C11 C 0.6496(16) 0.5544(17) 0.6390(12) 0.029(4) Uiso 1 1 d . . . . .
C12 C 0.4301(16) 0.8004(17) 0.6200(12) 0.029(4) Uiso 1 1 d . . . . .
C13 C 0.7225(16) 0.6537(17) 0.6555(12) 0.028(4) Uiso 1 1 d . . . . .
C14 C 0.3939(18) 0.4252(17) 0.6454(12) 0.033(4) Uiso 1 1 d . . . . .
C15 C 0.4473(18) 0.9159(19) 0.5778(14) 0.037(4) Uiso 1 1 d . . . . .
C16 C 0.8589(14) 0.6581(15) 0.6814(11) 0.023(3) Uiso 1 1 d . . . . .
C17 C 0.212(2) 0.845(2) 0.6490(14) 0.041(5) Uiso 1 1 d . . . . .
C18 C 0.3093(19) 0.766(2) 0.6572(14) 0.041(4) Uiso 1 1 d . . . . .
C19 C 0.2975(18) 0.3497(19) 0.6077(14) 0.037(4) Uiso 1 1 d . . . . .
C20 C 1.037(2) 0.538(2) 0.7028(16) 0.047(5) Uiso 1 1 d . . . . .
C21 C 0.2283(18) 0.9601(19) 0.6066(13) 0.035(4) Uiso 1 1 d . . . . .
C22 C 0.2835(17) 0.4729(18) 0.4536(13) 0.032(4) Uiso 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 C2 1.912(18) . ?
O1 C16 1.35(2) . ?
O1 C20 1.45(3) . ?
C2 C19 1.37(2) . ?
C2 C22 1.40(3) . ?
N1 C6 1.32(2) . ?
N1 C13 1.37(2) . ?
O4 C16 1.17(2) . ?
N2 C11 1.35(2) . ?
N2 C6 1.39(2) . ?
N2 C7 1.42(2) . ?
C6 C12 1.46(2) . ?
C7 C10 1.39(2) . ?
C7 C14 1.40(2) . ?
C9 C15 1.39(3) . ?
C9 C21 1.40(3) . ?
C10 C22 1.38(2) . ?
C11 C13 1.37(3) . ?
C12 C15 1.40(3) . ?
C12 C18 1.44(3) . ?
C13 C16 1.50(2) . ?
C14 C19 1.42(3) . ?
C17 C18 1.37(3) . ?
C17 C21 1.40(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
C16 O1 C20 113.7(16) . . ?
C19 C2 C22 122.6(18) . . ?
C19 C2 Br1 118.9(15) . . ?
C22 C2 Br1 118.4(12) . . ?
C6 N1 C13 106.1(15) . . ?
C11 N2 C6 107.1(15) . . ?
C11 N2 C7 123.7(16) . . ?
C6 N2 C7 128.8(15) . . ?
N1 C6 N2 110.1(15) . . ?
N1 C6 C12 124.6(16) . . ?
N2 C6 C12 125.2(15) . . ?
C10 C7 C14 121.2(16) . . ?
C10 C7 N2 119.5(15) . . ?
C14 C7 N2 119.3(15) . . ?
C15 C9 C21 120.7(18) . . ?
C22 C10 C7 120.0(16) . . ?
N2 C11 C13 106.6(16) . . ?
C15 C12 C18 119.5(17) . . ?
C15 C12 C6 118.6(16) . . ?
C18 C12 C6 121.8(17) . . ?
N1 C13 C11 110.0(15) . . ?
N1 C13 C16 121.8(16) . . ?
C11 C13 C16 128.2(17) . . ?
C7 C14 C19 118.6(16) . . ?
C9 C15 C12 119.5(18) . . ?
O4 C16 O1 127.2(16) . . ?
O4 C16 C13 123.9(16) . . ?
O1 C16 C13 108.9(14) . . ?
C18 C17 C21 121(2) . . ?
C17 C18 C12 119(2) . . ?
C2 C19 C14 118.9(18) . . ?
C17 C21 C9 119.4(19) . . ?
C10 C22 C2 118.5(15) . . ?

_refine_diff_density_max         6.215
_refine_diff_density_min         -3.911
_refine_diff_density_rms         0.247

_shelx_res_file                  
;

    11.res created by SHELXL-2014/7


TITL 11 in P2(1)2(1)2(1)
CELL 0.71073  10.7312  11.0728  12.9937  90.000  90.000  90.000
ZERR   19.00   0.0006   0.0006   0.0007   0.000   0.000   0.000
LATT -1
SYMM 0.5-X, -Y, 0.5+Z
SYMM -X, 0.5+Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C H N O BR
UNIT 19 19 19 19 19
TEMP 0

L.S. 4
BOND
FMAP 2
PLAN 20
ACTA

WGHT    0.100000
FVAR       0.40476
BR1   5    0.112570    0.275669    0.464808    11.00000    0.04699
O1    4    0.905347    0.544681    0.679121    11.00000    0.03443
C2    1    0.246048    0.374688    0.513646    11.00000    0.03138
N1    3    0.651930    0.756228    0.649028    11.00000    0.02406
O4    4    0.913765    0.747594    0.697684    11.00000    0.04102
N2    3    0.533772    0.595406    0.619523    11.00000    0.02910
C6    1    0.537549    0.720289    0.628108    11.00000    0.02458
C7    1    0.434819    0.520827    0.584033    11.00000    0.02278
C9    1    0.347014    0.995506    0.572895    11.00000    0.03605
C10   1    0.379001    0.545609    0.489544    11.00000    0.02888
C11   1    0.649621    0.554405    0.639030    11.00000    0.02903
C12   1    0.430142    0.800378    0.620015    11.00000    0.02874
C13   1    0.722511    0.653725    0.655533    11.00000    0.02817
C14   1    0.393907    0.425245    0.645409    11.00000    0.03288
C15   1    0.447292    0.915932    0.577750    11.00000    0.03660
C16   1    0.858863    0.658118    0.681383    11.00000    0.02348
C17   1    0.211955    0.845231    0.648987    11.00000    0.04144
C18   1    0.309252    0.765827    0.657237    11.00000    0.04080
C19   1    0.297548    0.349723    0.607695    11.00000    0.03700
C20   1    1.037063    0.538146    0.702842    11.00000    0.04656
C21   1    0.228315    0.960131    0.606614    11.00000    0.03487
C22   1    0.283460    0.472867    0.453642    11.00000    0.03224
HKLF 4

REM  11 in P2(1)2(1)2(1)
REM R1 =  0.1508 for    2694 Fo > 4sig(Fo)  and  0.1658 for all    3168 data
REM     89 parameters refined using      0 restraints

END

WGHT      0.1868     32.3749

REM Highest difference peak  6.215,  deepest hole -3.911,  1-sigma level  0.247
Q1    1   0.1054  0.2721  0.5031  11.00000  0.05    6.21
Q2    1   0.1199  0.2839  0.4288  11.00000  0.05    5.92
Q3    1   0.2510  0.3904  0.4742  11.00000  0.05    1.06
Q4    1   0.9096  0.7516  0.7340  11.00000  0.05    0.98
Q5    1   0.1891  0.2145  0.4973  11.00000  0.05    0.95
Q6    1   0.1278  0.2222  0.5753  11.00000  0.05    0.92
Q7    1   0.9260  0.7476  0.6620  11.00000  0.05    0.87
Q8    1   0.9098  0.5420  0.6407  11.00000  0.05    0.87
Q9    1   0.6497  0.7519  0.6816  11.00000  0.05    0.87
Q10   1   0.2712  0.4742  0.4199  11.00000  0.05    0.86
Q11   1   0.9101  0.5622  0.7115  11.00000  0.05    0.83
Q12   1   0.2335  0.3717  0.5518  11.00000  0.05    0.82
Q13   1   0.3265  0.7694  0.6228  11.00000  0.05    0.82
Q14   1   0.4127  0.5449  0.5422  11.00000  0.05    0.80
Q15   1   0.5399  0.5969  0.6534  11.00000  0.05    0.79
Q16   1   0.1748  0.3505  0.4746  11.00000  0.05    0.77
Q17   1   0.1827  0.2836  0.3604  11.00000  0.05    0.74
Q18   1   1.0613  0.5556  0.6547  11.00000  0.05    0.72
Q19   1   0.3678  1.0733  0.5460  11.00000  0.05    0.71
Q20   1   0.1359  0.2835  0.6450  11.00000  0.05    0.68
;
_shelx_res_checksum              42832
