# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_150126_hw1501
_database_code_depnum_ccdc_archive 'CCDC 1052977'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;
_audit_creation_date             2015-01-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H14 N2 O'
_chemical_formula_sum            'C16 H14 N2 O'
_chemical_formula_weight         250.29
_chemical_melting_point          513.15
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   13.1976(17)
_cell_length_b                   10.5014(8)
_cell_length_c                   9.8453(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.284(14)
_cell_angle_gamma                90.00
_cell_volume                     1295.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4437
_cell_measurement_theta_min      3.2448
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5056
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0014970000
_diffrn_orient_matrix_UB_12      0.0136474000
_diffrn_orient_matrix_UB_13      -0.0711607000
_diffrn_orient_matrix_UB_21      0.0564594000
_diffrn_orient_matrix_UB_22      0.0047811000
_diffrn_orient_matrix_UB_23      0.0229173000
_diffrn_orient_matrix_UB_31      0.0038277000
_diffrn_orient_matrix_UB_32      -0.0659783000
_diffrn_orient_matrix_UB_33      -0.0130118000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1639
_reflns_number_total             2359
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0601P)²+0.0719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1267
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.90111(11) 0.90622(10) 0.07662(13) 0.0401(4) Uani 1 d . . .
H1 H 0.9005 0.8893 -0.0049 0.060 Uiso 1 calc . . GR
N1 N 0.98062(13) 0.62289(15) 0.26994(17) 0.0429(4) Uani 1 d . . .
H1A H 1.0213(18) 0.558(2) 0.312(3) 0.071(7) Uiso 1 d . . .
N2 N 0.89161(12) 0.64527(14) 0.30426(17) 0.0424(4) Uani 1 d . . .
C1 C 0.69969(17) 0.90932(19) 0.1685(2) 0.0536(6) Uani 1 d . . .
H1B H 0.7354 0.9554 0.1169 0.064 Uiso 1 calc . . R
C2 C 0.60276(18) 0.9529(2) 0.1754(3) 0.0689(7) Uani 1 d . . .
H2 H 0.5738 1.0273 0.1275 0.083 Uiso 1 calc . . R
C3 C 0.54913(19) 0.8885(3) 0.2512(3) 0.0789(8) Uani 1 d . . .
H3 H 0.4841 0.9186 0.2562 0.095 Uiso 1 calc . . R
C4 C 0.5923(2) 0.7788(3) 0.3200(3) 0.0947(10) Uani 1 d . . .
H4 H 0.5565 0.7343 0.3727 0.114 Uiso 1 calc . . R
C5 C 0.68831(17) 0.7333(2) 0.3124(3) 0.0711(7) Uani 1 d . . .
H5 H 0.7157 0.6577 0.3586 0.085 Uiso 1 calc . . R
C6 C 0.74464(14) 0.79830(17) 0.2370(2) 0.0422(5) Uani 1 d . . .
C7 C 0.84845(14) 0.75091(16) 0.23184(19) 0.0365(4) Uani 1 d . . .
C8 C 0.91500(14) 0.79633(15) 0.15599(18) 0.0342(4) Uani 1 d . . .
C9 C 0.99927(14) 0.71127(15) 0.18099(19) 0.0375(4) Uani 1 d . . .
C10 C 1.08913(14) 0.70184(16) 0.12405(19) 0.0394(5) Uani 1 d . . .
C11 C 1.11963(17) 0.58529(19) 0.0833(2) 0.0543(6) Uani 1 d . . .
H11 H 1.0833 0.5120 0.0939 0.065 Uiso 1 calc . . R
C12 C 1.20263(18) 0.5761(2) 0.0275(2) 0.0634(6) Uani 1 d . . .
H12 H 1.2210 0.4968 0.0003 0.076 Uiso 1 calc . . R
C13 C 1.25916(17) 0.6820(2) 0.0112(2) 0.0615(6) Uani 1 d . . .
C14 C 1.22886(18) 0.7982(2) 0.0525(3) 0.0651(7) Uani 1 d . . .
H14 H 1.2659 0.8712 0.0426 0.078 Uiso 1 calc . . R
C15 C 1.14554(17) 0.80883(19) 0.1076(2) 0.0548(6) Uani 1 d . . .
H15 H 1.1269 0.8883 0.1340 0.066 Uiso 1 calc . . R
C16 C 1.3524(2) 0.6707(3) -0.0463(3) 0.0981(10) Uani 1 d . . .
H16A H 1.4171 0.6934 0.0273 0.147 Uiso 1 calc . . GR
H16B H 1.3418 0.7270 -0.1264 0.147 Uiso 1 calc . . GR
H16C H 1.3576 0.5846 -0.0763 0.147 Uiso 1 calc . . GR

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
O1 0.0540(8) 0.0344(6) 0.0373(7) 0.0031(6) 0.0222(7) 0.0024(5)
N1 0.0477(10) 0.0400(8) 0.0472(10) 0.0082(8) 0.0237(9) 0.0083(7)
N2 0.0469(9) 0.0423(9) 0.0446(9) 0.0073(7) 0.0239(8) 0.0044(7)
C1 0.0526(13) 0.0583(12) 0.0568(14) 0.0076(11) 0.0270(12) 0.0085(10)
C2 0.0582(15) 0.0751(15) 0.0769(17) 0.0117(13) 0.0259(14) 0.0222(12)
C3 0.0458(13) 0.104(2) 0.095(2) 0.0140(17) 0.0329(15) 0.0176(13)
C4 0.0604(16) 0.117(2) 0.126(3) 0.045(2) 0.0569(18) 0.0135(16)
C5 0.0514(13) 0.0769(15) 0.0960(19) 0.0316(14) 0.0390(14) 0.0082(12)
C6 0.0405(10) 0.0479(11) 0.0411(11) 0.0008(9) 0.0168(9) 0.0001(8)
C7 0.0424(10) 0.0347(9) 0.0357(10) -0.0006(8) 0.0170(9) -0.0004(8)
C8 0.0407(10) 0.0304(8) 0.0335(10) -0.0001(8) 0.0144(8) -0.0007(7)
C9 0.0440(11) 0.0368(9) 0.0350(10) 0.0009(8) 0.0172(9) -0.0037(8)
C10 0.0404(10) 0.0433(10) 0.0368(11) 0.0073(8) 0.0156(9) 0.0050(8)
C11 0.0533(13) 0.0521(12) 0.0647(14) -0.0037(10) 0.0287(12) 0.0028(9)
C12 0.0607(14) 0.0732(15) 0.0647(15) -0.0077(12) 0.0317(13) 0.0125(12)
C13 0.0473(13) 0.0938(17) 0.0502(13) 0.0143(12) 0.0251(11) 0.0121(12)
C14 0.0541(13) 0.0726(15) 0.0772(17) 0.0244(13) 0.0332(13) 0.0002(11)
C15 0.0535(12) 0.0499(12) 0.0675(15) 0.0105(10) 0.0283(12) 0.0032(10)
C16 0.0705(18) 0.151(3) 0.091(2) 0.0137(19) 0.0517(18) 0.0168(18)

_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
O1 H1 0.8200 . ?
O1 C8 1.3733(19) . ?
N1 H1A 0.88(2) . ?
N1 N2 1.341(2) . ?
N1 C9 1.351(2) . ?
N2 C7 1.345(2) . ?
C1 H1B 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.473(2) . ?
C7 C8 1.403(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.466(2) . ?
C10 C11 1.386(3) . ?
C10 C15 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 C14 1.385(3) . ?
C13 C16 1.512(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(3) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C8 O1 H1 109.5 . . ?
N2 N1 H1A 118.0(14) . . ?
N2 N1 C9 113.27(15) . . ?
C9 N1 H1A 128.6(14) . . ?
N1 N2 C7 105.65(13) . . ?
C2 C1 H1B 119.4 . . ?
C2 C1 C6 121.2(2) . . ?
C6 C1 H1B 119.4 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 118.9(2) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.1(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 117.16(18) . . ?
C1 C6 C7 121.94(16) . . ?
C5 C6 C7 120.91(18) . . ?
N2 C7 C6 120.27(15) . . ?
N2 C7 C8 109.33(14) . . ?
C8 C7 C6 130.36(16) . . ?
O1 C8 C7 126.48(15) . . ?
O1 C8 C9 126.77(15) . . ?
C9 C8 C7 106.71(15) . . ?
N1 C9 C8 104.99(15) . . ?
N1 C9 C10 122.38(15) . . ?
C8 C9 C10 132.51(15) . . ?
C11 C10 C9 120.90(16) . . ?
C15 C10 C9 121.27(16) . . ?
C15 C10 C11 117.83(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.3(2) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 117.43(19) . . ?
C12 C13 C16 121.0(2) . . ?
C14 C13 C16 121.5(2) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.8(2) . . ?
C15 C14 H14 119.1 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.41(19) . . ?
C14 C15 H15 119.8 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 C8 C9 N1 176.89(16) . . . . ?
O1 C8 C9 C10 -7.2(3) . . . . ?
N1 N2 C7 C6 175.77(16) . . . . ?
N1 N2 C7 C8 -2.2(2) . . . . ?
N1 C9 C10 C11 38.7(3) . . . . ?
N1 C9 C10 C15 -142.05(19) . . . . ?
N2 N1 C9 C8 -0.4(2) . . . . ?
N2 N1 C9 C10 -176.80(16) . . . . ?
N2 C7 C8 O1 -175.84(16) . . . . ?
N2 C7 C8 C9 2.1(2) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 N2 177.43(18) . . . . ?
C1 C6 C7 C8 -5.0(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 -179.47(19) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C5 C6 C7 N2 -2.0(3) . . . . ?
C5 C6 C7 C8 175.6(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C7 C8 O1 6.4(3) . . . . ?
C6 C7 C8 C9 -175.69(19) . . . . ?
C7 C8 C9 N1 -1.00(19) . . . . ?
C7 C8 C9 C10 174.89(19) . . . . ?
C8 C9 C10 C11 -136.6(2) . . . . ?
C8 C9 C10 C15 42.6(3) . . . . ?
C9 N1 N2 C7 1.7(2) . . . . ?
C9 C10 C11 C12 178.85(19) . . . . ?
C9 C10 C15 C14 -179.26(19) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 -0.3(4) . . . . ?
C11 C12 C13 C16 178.2(2) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C10 0.3(4) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C16 C13 C14 C15 -178.6(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
