# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_sudhri_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N2 O2'
_chemical_formula_weight         204.23

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           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_HALL  -P2yn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7124(4)
_cell_length_b                   8.9272(4)
_cell_length_c                   14.9003(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.869(3)
_cell_angle_gamma                90.00
_cell_volume                     1016.23(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3982
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      24.70

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9888
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   SADABS

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17324
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         29.21
_reflns_number_total             2735
_reflns_number_gt                2017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0779P)²+0.2813P] 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         2735
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1591
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.28089(19) 0.49089(17) -0.08142(10) 0.0383(3) Uani 1 1 d . . .
C2 C 0.2340(2) 0.34154(19) -0.09290(11) 0.0458(4) Uani 1 1 d . . .
H2 H 0.2399 0.2935 -0.1478 0.055 Uiso 1 1 calc R . .
C3 C 0.1788(2) 0.26558(18) -0.02164(11) 0.0457(4) Uani 1 1 d . . .
H3 H 0.1473 0.1654 -0.0294 0.055 Uiso 1 1 calc R . .
C4 C 0.16801(19) 0.33419(18) 0.06300(10) 0.0394(4) Uani 1 1 d . . .
C5 C 0.21649(19) 0.48699(17) 0.07343(10) 0.0391(3) Uani 1 1 d . . .
H5 H 0.2117 0.5366 0.1279 0.047 Uiso 1 1 calc R . .
C6 C 0.27047(18) 0.55960(17) 0.00141(10) 0.0359(3) Uani 1 1 d . . .
C7 C 0.3257(2) 0.71860(17) -0.00599(11) 0.0404(4) Uani 1 1 d . . .
C8 C 0.3438(2) 0.60140(18) -0.14241(11) 0.0423(4) Uani 1 1 d . . .
C9 C 0.1165(3) 0.3212(3) 0.22130(12) 0.0667(6) Uani 1 1 d . . .
H9A H 0.0723 0.2503 0.2610 0.100 Uiso 1 1 calc R . .
H9B H 0.0455 0.4099 0.2174 0.100 Uiso 1 1 calc R . .
H9C H 0.2351 0.3467 0.2447 0.100 Uiso 1 1 calc R . .
C10 C 0.0617(3) 0.0999(2) 0.12057(14) 0.0565(5) Uani 1 1 d . . .
H10A H 0.0260 0.0626 0.1756 0.085 Uiso 1 1 calc R . .
H10B H 0.1596 0.0428 0.1062 0.085 Uiso 1 1 calc R . .
H10C H -0.0337 0.0910 0.0722 0.085 Uiso 1 1 calc R . .
C11 C 0.4300(2) 0.8733(2) -0.12864(14) 0.0546(5) Uani 1 1 d . . .
H11A H 0.4509 0.8581 -0.1900 0.082 Uiso 1 1 calc R . .
H11B H 0.5369 0.9033 -0.0923 0.082 Uiso 1 1 calc R . .
H11C H 0.3433 0.9501 -0.1270 0.082 Uiso 1 1 calc R . .
N1 N 0.36782(18) 0.73468(15) -0.09313(9) 0.0421(3) Uani 1 1 d . . .
N2 N 0.1116(2) 0.25603(17) 0.13226(10) 0.0502(4) Uani 1 1 d . . .
O1 O 0.33243(19) 0.81685(14) 0.04987(9) 0.0590(4) Uani 1 1 d . . .
O2 O 0.37125(19) 0.58888(16) -0.22045(8) 0.0613(4) 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 0.0418(8) 0.0379(8) 0.0352(8) -0.0020(6) 0.0059(6) 0.0004(6)
C2 0.0584(10) 0.0403(9) 0.0393(8) -0.0088(7) 0.0092(7) -0.0031(7)
C3 0.0575(10) 0.0334(8) 0.0470(9) -0.0052(7) 0.0098(7) -0.0050(7)
C4 0.0390(7) 0.0388(8) 0.0405(8) 0.0018(6) 0.0062(6) 0.0001(6)
C5 0.0442(8) 0.0384(8) 0.0353(8) -0.0047(6) 0.0072(6) 0.0003(6)
C6 0.0360(7) 0.0334(7) 0.0380(8) -0.0030(6) 0.0040(5) 0.0011(5)
C7 0.0417(8) 0.0365(8) 0.0433(8) -0.0018(6) 0.0065(6) -0.0011(6)
C8 0.0442(8) 0.0438(9) 0.0393(8) 0.0006(7) 0.0072(6) -0.0004(6)
C9 0.0900(15) 0.0698(14) 0.0437(10) 0.0030(9) 0.0217(10) -0.0072(11)
C10 0.0594(11) 0.0463(10) 0.0660(12) 0.0132(9) 0.0159(9) -0.0043(8)
C11 0.0578(11) 0.0446(10) 0.0622(11) 0.0117(8) 0.0118(8) -0.0075(8)
N1 0.0471(7) 0.0363(7) 0.0434(7) 0.0014(5) 0.0084(5) -0.0037(5)
N2 0.0628(9) 0.0455(8) 0.0444(8) 0.0049(6) 0.0151(6) -0.0051(7)
O1 0.0815(9) 0.0393(7) 0.0583(8) -0.0131(6) 0.0175(6) -0.0086(6)
O2 0.0834(10) 0.0630(9) 0.0408(7) -0.0009(6) 0.0204(6) -0.0084(7)

_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 C2 1.386(2) . ?
C1 C6 1.3904(19) . ?
C1 C8 1.468(2) . ?
C2 C3 1.376(2) . ?
C3 C4 1.415(2) . ?
C4 N2 1.365(2) . ?
C4 C5 1.417(2) . ?
C5 C6 1.367(2) . ?
C6 C7 1.490(2) . ?
C7 O1 1.205(2) . ?
C7 N1 1.388(2) . ?
C8 O2 1.215(2) . ?
C8 N1 1.397(2) . ?
C9 N2 1.444(2) . ?
C10 N2 1.450(2) . ?
C11 N1 1.453(2) . ?

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 C1 C6 119.23(14) . . ?
C2 C1 C8 132.28(14) . . ?
C6 C1 C8 108.49(14) . . ?
C3 C2 C1 118.82(14) . . ?
C2 C3 C4 122.46(15) . . ?
N2 C4 C3 121.08(15) . . ?
N2 C4 C5 121.03(14) . . ?
C3 C4 C5 117.89(14) . . ?
C6 C5 C4 118.33(13) . . ?
C5 C6 C1 123.27(14) . . ?
C5 C6 C7 129.10(13) . . ?
C1 C6 C7 107.62(13) . . ?
O1 C7 N1 125.23(15) . . ?
O1 C7 C6 128.89(15) . . ?
N1 C7 C6 105.87(12) . . ?
O2 C8 N1 123.60(16) . . ?
O2 C8 C1 130.24(16) . . ?
N1 C8 C1 106.15(13) . . ?
C7 N1 C8 111.86(13) . . ?
C7 N1 C11 124.05(14) . . ?
C8 N1 C11 124.10(14) . . ?
C4 N2 C9 121.17(15) . . ?
C4 N2 C10 120.48(15) . . ?
C9 N2 C10 118.07(15) . . ?

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
C6 C1 C2 C3 -0.1(2) . . . . ?
C8 C1 C2 C3 -179.96(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 N2 179.60(16) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
N2 C4 C5 C6 -179.44(15) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C7 179.10(14) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C8 C1 C6 C5 -179.83(14) . . . . ?
C2 C1 C6 C7 -179.22(14) . . . . ?
C8 C1 C6 C7 0.67(16) . . . . ?
C5 C6 C7 O1 -0.9(3) . . . . ?
C1 C6 C7 O1 178.60(17) . . . . ?
C5 C6 C7 N1 179.89(15) . . . . ?
C1 C6 C7 N1 -0.65(16) . . . . ?
C2 C1 C8 O2 0.0(3) . . . . ?
C6 C1 C8 O2 -179.87(17) . . . . ?
C2 C1 C8 N1 179.42(17) . . . . ?
C6 C1 C8 N1 -0.44(17) . . . . ?
O1 C7 N1 C8 -178.91(16) . . . . ?
C6 C7 N1 C8 0.38(17) . . . . ?
O1 C7 N1 C11 1.3(3) . . . . ?
C6 C7 N1 C11 -179.42(14) . . . . ?
O2 C8 N1 C7 179.49(16) . . . . ?
C1 C8 N1 C7 0.02(18) . . . . ?
O2 C8 N1 C11 -0.7(3) . . . . ?
C1 C8 N1 C11 179.82(14) . . . . ?
C3 C4 N2 C9 173.92(17) . . . . ?
C5 C4 N2 C9 -6.5(3) . . . . ?
C3 C4 N2 C10 0.2(3) . . . . ?
C5 C4 N2 C10 179.73(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        29.21
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041
_database_code_depnum_ccdc_archive 'CCDC 993237'
