# Electronic Supplementary Material (ESI) for Green 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_20141103-01
_audit_block_doi                 10.5517/cc13xb5j
_database_code_depnum_ccdc_archive 'CCDC 1040117'
_audit_update_record             
;
2014-12-18 deposited with the CCDC.
2015-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H7 N O'
_chemical_formula_weight         133.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.5044(13)
_cell_length_b                   11.9291(19)
_cell_length_c                   14.8473(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1329.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1860
_cell_measurement_theta_min      3.217
_cell_measurement_theta_max      28.652

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63215
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4238
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.416
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1228
_reflns_number_gt                974
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0789P)²+0.1460P] 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     SHELXL
_refine_ls_extinction_coef       0.26(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1228
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_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
N1 N 0.4892(2) 0.19551(15) -0.06781(10) 0.0604(5) Uani 1 1 d . . . . .
O1 O 0.13489(18) 0.02010(12) 0.15621(8) 0.0635(5) Uani 1 1 d . . . . .
C1 C 0.2946(2) 0.08595(13) 0.02607(10) 0.0396(5) Uani 1 1 d . . . . .
C2 C 0.2422(2) 0.08304(14) 0.12174(10) 0.0436(5) Uani 1 1 d . . . . .
C3 C 0.3477(2) 0.17319(15) 0.16974(10) 0.0522(5) Uani 1 1 d . . . . .
H3A H 0.4242 0.1401 0.2152 0.063 Uiso 1 1 calc R U . . .
H3B H 0.2680 0.2260 0.1988 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4594(3) 0.23236(16) 0.09795(12) 0.0582(6) Uani 1 1 d . . . . .
H4A H 0.4268 0.3108 0.0933 0.070 Uiso 1 1 calc R U . . .
H4B H 0.5855 0.2270 0.1118 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4164(2) 0.17080(13) 0.01221(10) 0.0453(5) Uani 1 1 d . . . . .
C6 C 0.4337(3) 0.12988(19) -0.13580(11) 0.0614(6) Uani 1 1 d . . . . .
H6 H 0.4810 0.1438 -0.1926 0.074 Uiso 1 1 calc R U . . .
C7 C 0.3129(2) 0.04396(17) -0.12832(11) 0.0557(6) Uani 1 1 d . . . . .
H7 H 0.2803 0.0028 -0.1789 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2400(2) 0.01903(15) -0.04550(10) 0.0468(5) Uani 1 1 d . . . . .
H8 H 0.1590 -0.0392 -0.0379 0.056 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
N1 C5 1.3406(19) . ?
N1 C6 1.344(3) . ?
O1 C2 1.214(2) . ?
C1 C5 1.379(2) . ?
C1 C8 1.391(2) . ?
C1 C2 1.474(2) . ?
C2 C3 1.514(2) . ?
C3 C4 1.529(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.505(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
C5 N1 C6 114.29(16) . . ?
C5 C1 C8 120.16(15) . . ?
C5 C1 C2 109.73(14) . . ?
C8 C1 C2 130.11(15) . . ?
O1 C2 C1 126.69(15) . . ?
O1 C2 C3 125.99(15) . . ?
C1 C2 C3 107.31(14) . . ?
C2 C3 C4 106.65(13) . . ?
C2 C3 H3A 110.4 . . ?
C4 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C4 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 104.28(14) . . ?
C5 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
C5 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
N1 C5 C1 124.32(15) . . ?
N1 C5 C4 123.70(16) . . ?
C1 C5 C4 111.98(14) . . ?
N1 C6 C7 125.38(16) . . ?
N1 C6 H6 117.3 . . ?
C7 C6 H6 117.3 . . ?
C6 C7 C8 119.68(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C1 116.18(17) . . ?
C7 C8 H8 121.9 . . ?
C1 C8 H8 121.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 O1 178.43(16) . . . . ?
C8 C1 C2 O1 -1.5(3) . . . . ?
C5 C1 C2 C3 -1.75(18) . . . . ?
C8 C1 C2 C3 178.33(17) . . . . ?
O1 C2 C3 C4 -178.13(17) . . . . ?
C1 C2 C3 C4 2.05(18) . . . . ?
C2 C3 C4 C5 -1.58(18) . . . . ?
C6 N1 C5 C1 0.0(3) . . . . ?
C6 N1 C5 C4 179.53(16) . . . . ?
C8 C1 C5 N1 0.2(3) . . . . ?
C2 C1 C5 N1 -179.68(15) . . . . ?
C8 C1 C5 C4 -179.33(15) . . . . ?
C2 C1 C5 C4 0.74(19) . . . . ?
C3 C4 C5 N1 -179.02(16) . . . . ?
C3 C4 C5 C1 0.6(2) . . . . ?
C5 N1 C6 C7 0.2(3) . . . . ?
N1 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C1 0.8(3) . . . . ?
C5 C1 C8 C7 -0.7(2) . . . . ?
C2 C1 C8 C7 179.25(15) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4



