# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_D648

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Br N3 O2'
_chemical_formula_weight         282.10

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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'
'-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                   11.4437(4)
_cell_length_b                   22.5577(8)
_cell_length_c                   8.1293(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2098.53(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8383
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      28.26

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.342
_exptl_crystal_size_min          0.272
_exptl_absorpt_coefficient_mu    3.905
_shelx_estimated_absorpt_T_min   0.306
_shelx_estimated_absorpt_T_max   0.416
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5116
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17942
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.995
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2420
_reflns_number_gt                2127
_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.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing.cell_refinement       'APEX2 v2013.6--2 (Bruker AXS)'
_computing.data_collection       'APEX2 (Bruker AXS)'
_computing.data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing.molecular_graphics    'Bruker SHELXTL'
_computing.publication_material  'Bruker SHELXTL'
_computing.structure_refinement  'SHELXL--2013 (Sheldrick 2013)'
_computing.structure_solution    'SHELXS--97 (Sheldrick 2008)'

_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)+(0.0318P)²+1.0324P] 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         2420
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0597
_refine_ls_wR_factor_gt          0.0576
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_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 0.92973(2) 0.72875(2) 0.78891(2) 0.01928(7) Uani 1 1 d . . . . .
O1 O 0.97704(11) 0.40436(6) -0.02087(16) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.79015(11) 0.37278(5) -0.02072(16) 0.0199(3) Uani 1 1 d . . . . .
N1 N 0.72351(13) 0.46494(6) 0.18234(18) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.71908(13) 0.50941(7) 0.28445(17) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.83130(12) 0.52825(6) 0.30915(16) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.82578(17) 0.32756(8) -0.1370(2) 0.0243(4) Uani 1 1 d . . . . .
H1A H 0.8582 0.3465 -0.2355 0.036 Uiso 1 1 calc R U . . .
H1B H 0.7579 0.3035 -0.1676 0.036 Uiso 1 1 calc R U . . .
H1C H 0.8853 0.3022 -0.0865 0.036 Uiso 1 1 calc R U . . .
C2 C 0.87733(14) 0.40897(7) 0.0252(2) 0.0157(3) Uani 1 1 d . . . . .
C3 C 0.83748(14) 0.45511(7) 0.1404(2) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.90678(15) 0.49528(8) 0.2205(2) 0.0147(3) Uani 1 1 d . . . . .
H4 H 0.9894 0.4991 0.2150 0.018 Uiso 1 1 calc R U . . .
C5 C 0.85435(14) 0.57638(7) 0.4194(2) 0.0137(3) Uani 1 1 d . . . . .
C6 C 0.96915(15) 0.58918(8) 0.4618(2) 0.0175(3) Uani 1 1 d . . . . .
H6 H 1.0318 0.5668 0.4167 0.021 Uiso 1 1 calc R U . . .
C7 C 0.99112(15) 0.63513(8) 0.5711(2) 0.0184(4) Uani 1 1 d . . . . .
H7 H 1.0691 0.6445 0.6018 0.022 Uiso 1 1 calc R U . . .
C8 C 0.89868(15) 0.66717(8) 0.6350(2) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.76169(14) 0.60884(7) 0.4823(2) 0.0160(3) Uani 1 1 d . . . . .
H11 H 0.6837 0.5997 0.4512 0.019 Uiso 1 1 calc R U . . .
C12 C 0.78420(15) 0.65482(8) 0.5913(2) 0.0167(3) Uani 1 1 d . . . . .
H12 H 0.7218 0.6776 0.6355 0.020 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 C8 1.9028(18) . ?
O1 C2 1.205(2) . ?
O2 C2 1.342(2) . ?
O2 C1 1.449(2) . ?
N1 N2 1.303(2) . ?
N1 C3 1.366(2) . ?
N2 N3 1.368(2) . ?
N3 C4 1.348(2) . ?
N3 C5 1.432(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.473(2) . ?
C3 C4 1.369(2) . ?
C4 H4 0.9500 . ?
C5 C11 1.386(2) . ?
C5 C6 1.389(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(2) . ?
C7 H7 0.9500 . ?
C8 C12 1.386(2) . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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
C2 O2 C1 113.60(14) . . ?
N2 N1 C3 108.72(14) . . ?
N1 N2 N3 107.23(13) . . ?
C4 N3 N2 110.60(14) . . ?
C4 N3 C5 129.37(14) . . ?
N2 N3 C5 120.02(13) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 124.38(16) . . ?
O1 C2 C3 123.49(15) . . ?
O2 C2 C3 112.12(14) . . ?
N1 C3 C4 109.08(15) . . ?
N1 C3 C2 124.68(15) . . ?
C4 C3 C2 126.23(15) . . ?
N3 C4 C3 104.37(15) . . ?
N3 C4 H4 127.8 . . ?
C3 C4 H4 127.8 . . ?
C11 C5 C6 121.48(16) . . ?
C11 C5 N3 119.36(15) . . ?
C6 C5 N3 119.15(14) . . ?
C7 C6 C5 119.04(16) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C6 119.50(16) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C12 121.46(16) . . ?
C7 C8 Br1 119.07(13) . . ?
C12 C8 Br1 119.46(13) . . ?
C5 C11 C12 119.22(15) . . ?
C5 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C8 C12 C11 119.30(15) . . ?
C8 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-3



_database_code_depnum_ccdc_archive 'CCDC 1021699'
