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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130832

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N2 O2'
_chemical_formula_weight         250.25

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3094(4)
_cell_length_b                   7.4430(5)
_cell_length_c                   13.8773(8)
_cell_angle_alpha                80.486(3)
_cell_angle_beta                 79.734(3)
_cell_angle_gamma                72.162(2)
_cell_volume                     606.15(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2051
_cell_measurement_theta_min      3.0046
_cell_measurement_theta_max      22.4159

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            'Pale Orange'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8382
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9021
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         26.42
_reflns_number_total             2464
_reflns_number_gt                1219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1010P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1932
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1240(6) 0.2910(5) 0.1739(2) 0.0584(9) Uani 1 1 d . . .
C2 C 0.2477(5) 0.2738(4) 0.2538(2) 0.0469(8) Uani 1 1 d . . .
C3 C 0.1360(5) 0.3322(4) 0.3432(2) 0.0524(8) Uani 1 1 d . . .
H3 H -0.0190 0.3862 0.3508 0.063 Uiso 1 1 calc R . .
C4 C 0.2529(5) 0.3110(4) 0.4216(2) 0.0489(8) Uani 1 1 d . . .
H4 H 0.1768 0.3508 0.4817 0.059 Uiso 1 1 calc R . .
C5 C 0.4820(5) 0.2311(4) 0.41065(19) 0.0400(7) Uani 1 1 d . . .
C6 C 0.5946(5) 0.1756(4) 0.3201(2) 0.0538(8) Uani 1 1 d . . .
H6 H 0.7499 0.1237 0.3121 0.065 Uiso 1 1 calc R . .
C7 C 0.4787(5) 0.1966(4) 0.2429(2) 0.0545(9) Uani 1 1 d . . .
H7 H 0.5554 0.1589 0.1825 0.065 Uiso 1 1 calc R . .
C8 C 0.5512(5) 0.2639(4) 0.5767(2) 0.0457(8) Uani 1 1 d . . .
C9 C 0.7478(5) 0.1962(4) 0.6389(2) 0.0439(7) Uani 1 1 d . . .
C10 C 0.7149(5) 0.2325(4) 0.7426(2) 0.0445(7) Uani 1 1 d . . .
C11 C 0.5071(5) 0.2850(5) 0.7994(2) 0.0629(10) Uani 1 1 d . . .
H11 H 0.3765 0.3063 0.7718 0.075 Uiso 1 1 calc R . .
C12 C 0.4948(6) 0.3059(6) 0.8985(2) 0.0820(12) Uani 1 1 d . . .
H12 H 0.3553 0.3399 0.9370 0.098 Uiso 1 1 calc R . .
C13 C 0.6857(7) 0.2769(5) 0.9393(2) 0.0759(11) Uani 1 1 d . . .
H13 H 0.6755 0.2917 1.0053 0.091 Uiso 1 1 calc R . .
C14 C 0.8922(6) 0.2260(5) 0.8835(2) 0.0684(10) Uani 1 1 d . . .
H14 H 1.0222 0.2058 0.9115 0.082 Uiso 1 1 calc R . .
C15 C 0.9056(5) 0.2050(4) 0.7860(2) 0.0567(9) Uani 1 1 d . . .
H15 H 1.0460 0.1715 0.7482 0.068 Uiso 1 1 calc R . .
N1 N 0.0236(5) 0.2999(5) 0.1113(2) 0.0859(10) Uani 1 1 d . . .
N2 N 0.6122(4) 0.1981(3) 0.48780(16) 0.0467(7) Uani 1 1 d . . .
H2 H 0.7480 0.1268 0.4769 0.056 Uiso 1 1 calc R . .
O1 O 0.3682(4) 0.3654(3) 0.60474(16) 0.0697(7) Uani 1 1 d . . .
O2 O 0.9311(3) 0.1134(3) 0.59808(15) 0.0609(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.064(2) 0.060(2) 0.053(2) -0.0057(16) -0.0151(17) -0.0158(18)
C2 0.054(2) 0.0433(18) 0.0455(17) -0.0009(14) -0.0147(15) -0.0143(15)
C3 0.0410(18) 0.059(2) 0.0553(19) -0.0082(16) -0.0106(15) -0.0078(16)
C4 0.0453(19) 0.056(2) 0.0435(16) -0.0095(14) -0.0050(14) -0.0098(15)
C5 0.0398(17) 0.0383(17) 0.0407(16) -0.0040(13) -0.0098(13) -0.0071(13)
C6 0.0433(18) 0.065(2) 0.0450(17) -0.0131(15) -0.0058(14) 0.0000(16)
C7 0.053(2) 0.065(2) 0.0411(17) -0.0116(15) -0.0071(15) -0.0071(17)
C8 0.0460(19) 0.0462(19) 0.0428(17) -0.0069(14) -0.0066(14) -0.0086(15)
C9 0.0457(19) 0.0401(17) 0.0439(16) -0.0052(13) -0.0079(14) -0.0081(14)
C10 0.0508(19) 0.0441(18) 0.0408(16) -0.0069(13) -0.0107(14) -0.0134(14)
C11 0.054(2) 0.089(3) 0.0505(19) -0.0175(18) -0.0056(16) -0.0224(19)
C12 0.070(3) 0.126(4) 0.054(2) -0.027(2) 0.0066(19) -0.033(2)
C13 0.090(3) 0.101(3) 0.046(2) -0.018(2) -0.011(2) -0.036(3)
C14 0.069(2) 0.081(3) 0.061(2) -0.0156(19) -0.0237(19) -0.016(2)
C15 0.054(2) 0.065(2) 0.0519(19) -0.0155(16) -0.0103(15) -0.0114(17)
N1 0.091(2) 0.102(3) 0.073(2) -0.0124(19) -0.0362(19) -0.024(2)
N2 0.0388(14) 0.0524(16) 0.0421(14) -0.0099(11) -0.0075(11) 0.0005(12)
O1 0.0485(14) 0.0886(18) 0.0623(14) -0.0337(13) -0.0134(11) 0.0107(13)
O2 0.0469(14) 0.0749(17) 0.0526(13) -0.0185(11) -0.0095(10) 0.0017(12)

_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
C1 N1 1.146(4) . ?
C1 C2 1.435(5) . ?
C2 C3 1.380(4) . ?
C2 C7 1.383(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 N2 1.409(3) . ?
C6 C7 1.364(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.208(3) . ?
C8 N2 1.351(3) . ?
C8 C9 1.547(4) . ?
C9 O2 1.218(3) . ?
C9 C10 1.474(4) . ?
C10 C11 1.383(4) . ?
C10 C15 1.385(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N2 H2 0.8600 . ?

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
N1 C1 C2 177.9(4) . . ?
C3 C2 C7 119.3(3) . . ?
C3 C2 C1 120.0(3) . . ?
C7 C2 C1 120.7(3) . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 N2 123.4(2) . . ?
C6 C5 N2 117.0(3) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
O1 C8 N2 125.1(3) . . ?
O1 C8 C9 123.4(3) . . ?
N2 C8 C9 111.5(3) . . ?
O2 C9 C10 121.6(3) . . ?
O2 C9 C8 117.0(3) . . ?
C10 C9 C8 121.4(3) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C9 124.1(3) . . ?
C15 C10 C9 117.3(3) . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 119.4(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
C8 N2 C5 128.3(3) . . ?
C8 N2 H2 115.8 . . ?
C5 N2 H2 115.8 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.42
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.102
_database_code_depnum_ccdc_archive 'CCDC 966115'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130958lt_0m
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a                   16.806(3)
_cell_length_b                   5.5338(9)
_cell_length_c                   18.763(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.944(6)
_cell_angle_gamma                90.00
_cell_volume                     1735.6
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O1 O -0.19746(10) 0.9807(3) 0.28677(10)
O2 O 0.16566(11) 1.0360(3) 0.45244(10)
O3 O 0.09500(10) 0.5176(3) 0.52988(9)
N1 N 0.04176(12) 0.8561(4) 0.43613(11)
H1 H 0.0153 0.7310 0.4504
C1 C -0.44816(17) 0.6671(5) 0.15828(14)
H1A H -0.4944 0.5746 0.1430
C2 C -0.45513(16) 0.8797(5) 0.19587(14)
H2 H -0.5062 0.9333 0.2068
C3 C -0.38720(16) 1.0144(5) 0.21756(14)
H3 H -0.3923 1.1607 0.2432
C4 C -0.31222(16) 0.9392(5) 0.20244(14)
C5 C -0.23983(16) 1.0908(5) 0.22448(14)
H5A H -0.2050 1.0988 0.1851
H5B H -0.2561 1.2572 0.2358
C6 C -0.12355(15) 1.0770(5) 0.30934(13)
C7 C -0.07835(15) 0.9381(5) 0.36043(13)
H7 H -0.0998 0.7934 0.3778
C8 C -0.00183(15) 1.0119(4) 0.38578(13)
C9 C 0.11865(15) 0.8761(5) 0.46472(14)
C10 C 0.14454(15) 0.6652(5) 0.51585(12)
C11 C 0.23211(14) 0.6516(5) 0.54230(13)
H11 H 0.2499 0.8140 0.5611
C12 C 0.24962(16) 0.4667(5) 0.60186(14)
H12A H 0.2293 0.3065 0.5850
H12B H 0.2214 0.5135 0.6435
C13 C 0.33949(16) 0.4498(5) 0.62485(14)
H13A H 0.3590 0.6067 0.6451
H13B H 0.3494 0.3257 0.6627
C14 C 0.38552(16) 0.3843(5) 0.56182(15)
H14A H 0.3696 0.2209 0.5442
H14B H 0.4436 0.3816 0.5777
C15 C -0.37315(17) 0.5893(5) 0.14291(15)
H15 H -0.3682 0.4432 0.1172
C16 C -0.30558(16) 0.7244(5) 0.16507(14)
H16 H -0.2545 0.6699 0.1546
C17 C -0.09388(15) 1.2922(5) 0.28546(13)
H17 H -0.1252 1.3890 0.2514
C18 C -0.01764(15) 1.3637(5) 0.31209(13)
H18 H 0.0030 1.5112 0.2958
C19 C 0.02945(15) 1.2267(4) 0.36184(13)
H19 H 0.0818 1.2781 0.3792
C20 C 0.36874(15) 0.5673(5) 0.50113(14)
H20A H 0.3901 0.7271 0.5172
H20B H 0.3966 0.5163 0.4596
C21 C 0.27928(15) 0.5889(5) 0.47811(14)
H21A H 0.2593 0.4342 0.4566
H21B H 0.2701 0.7163 0.4411

#END
_database_code_depnum_ccdc_archive 'CCDC 966320'
