# 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_shelx
_audit_block_doi                 10.5517/cc1j1drq
_database_code_depnum_ccdc_archive 'CCDC 1401533'
_audit_update_record             
;
2015-05-16 deposited with the CCDC.
2015-07-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3-Hydroxyquinolones
_chemical_name_common            3-HQ
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   9.0099(12)
_cell_length_b                   9.0949(15)
_cell_length_c                   9.526(2)
_cell_angle_alpha                115.448(19)
_cell_angle_beta                 114.236(18)
_cell_angle_gamma                96.055(13)
_cell_volume                     603.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10199
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.365
_diffrn_reflns_theta_max         29.789
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3015
_reflns_number_gt                2353
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0904P)²+0.1218P] 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         3015
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
C1 C 0.23889(18) 0.50338(17) 0.22245(18) 0.0204(3) Uani 1 1 d . . . . .
C2 C 0.16707(19) 0.32830(18) 0.14065(19) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.1358(2) 0.20999(18) -0.03557(19) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.1785(2) 0.18280(19) -0.28479(19) 0.0241(3) Uani 1 1 d . . . . .
H4 H 0.1305 0.0630 -0.3433 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2334(2) 0.2541(2) -0.36355(19) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.2220 0.1829 -0.4751 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3062(2) 0.4335(2) -0.2757(2) 0.0265(3) Uani 1 1 d . . . . .
H6 H 0.3440 0.4814 -0.3291 0.032 Uiso 1 1 calc R U . . .
C7 C 0.32291(19) 0.54060(19) -0.1114(2) 0.0237(3) Uani 1 1 d . . . . .
H7 H 0.3718 0.6601 -0.0543 0.028 Uiso 1 1 calc R U . . .
C8 C 0.26594(18) 0.46968(18) -0.02893(18) 0.0204(3) Uani 1 1 d . . . . .
C9 C 0.19414(18) 0.28925(18) -0.11585(18) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.3250(2) 0.76203(18) 0.2079(2) 0.0305(4) Uani 1 1 d . . . . .
H10A H 0.4455 0.8129 0.2521 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3017 0.8143 0.3045 0.046 Uiso 1 1 calc R U . . .
H10C H 0.2561 0.7812 0.1136 0.046 Uiso 1 1 calc R U . . .
C11 C 0.27714(19) 0.62079(17) 0.40932(18) 0.0214(3) Uani 1 1 d . . . . .
C12A C 0.1427(2) 0.63234(18) 0.44421(19) 0.0254(3) Uani 1 1 d . . . . .
H12A H 0.0291 0.5646 0.3512 0.031 Uiso 1 1 calc R U . . .
C12B C 0.44720(19) 0.71765(18) 0.55001(19) 0.0258(3) Uani 1 1 d . . . . .
H12B H 0.5382 0.7076 0.5281 0.031 Uiso 1 1 calc R U . . .
C13A C 0.1763(2) 0.74397(19) 0.6165(2) 0.0288(4) Uani 1 1 d . . . . .
H13A H 0.0856 0.7518 0.6393 0.035 Uiso 1 1 calc R U . . .
C13B C 0.4811(2) 0.82929(18) 0.72313(19) 0.0288(4) Uani 1 1 d . . . . .
H13B H 0.5947 0.8940 0.8173 0.035 Uiso 1 1 calc R U . . .
C14 C 0.3455(2) 0.84399(19) 0.75503(19) 0.0288(4) Uani 1 1 d . . . . .
H14 H 0.3679 0.9215 0.8702 0.035 Uiso 1 1 calc R U . . .
N1 N 0.28175(16) 0.57524(15) 0.13658(15) 0.0215(3) Uani 1 1 d . . . . .
O1 O 0.12911(16) 0.26365(13) 0.23161(14) 0.0307(3) Uani 1 1 d . . . . .
H1 H 0.0732 0.1597 0.1631 0.046 Uiso 1 1 calc R U . . .
O2 O 0.06819(17) 0.05053(13) -0.10979(15) 0.0373(3) Uani 1 1 d . . . . .


_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 1.365(2) . ?
C1 N1 1.3824(17) . ?
C1 C11 1.4876(19) . ?
C2 O1 1.3610(16) . ?
C2 C3 1.4319(19) . ?
C3 O2 1.2462(18) . ?
C3 C9 1.4509(19) . ?
C4 C5 1.372(2) . ?
C4 C9 1.4119(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.374(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.3835(18) . ?
C8 C9 1.402(2) . ?
C10 N1 1.4665(19) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12A 1.385(2) . ?
C11 C12B 1.391(2) . ?
C12A C13A 1.383(2) . ?
C12A H12A 0.9300 . ?
C12B C13B 1.388(2) . ?
C12B H12B 0.9300 . ?
C13A C14 1.384(2) . ?
C13A H13A 0.9300 . ?
C13B C14 1.381(2) . ?
C13B H13B 0.9300 . ?
C14 H14 0.9300 . ?
O1 H1 0.8200 . ?

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 N1 121.22(12) . . ?
C2 C1 C11 120.19(12) . . ?
N1 C1 C11 118.57(12) . . ?
O1 C2 C1 119.02(12) . . ?
O1 C2 C3 118.86(12) . . ?
C1 C2 C3 122.08(13) . . ?
O2 C3 C2 121.50(13) . . ?
O2 C3 C9 123.36(12) . . ?
C2 C3 C9 115.10(12) . . ?
C5 C4 C9 120.73(14) . . ?
C5 C4 H4 119.6 . . ?
C9 C4 H4 119.6 . . ?
C4 C5 C6 119.79(13) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.87(13) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.14(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C9 119.75(13) . . ?
N1 C8 C7 121.04(13) . . ?
C9 C8 C7 119.21(13) . . ?
C8 C9 C4 119.26(13) . . ?
C8 C9 C3 121.30(12) . . ?
C4 C9 C3 119.44(13) . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12A C11 C12B 119.61(13) . . ?
C12A C11 C1 119.83(13) . . ?
C12B C11 C1 120.56(13) . . ?
C13A C12A C11 120.35(14) . . ?
C13A C12A H12A 119.8 . . ?
C11 C12A H12A 119.8 . . ?
C13B C12B C11 120.02(14) . . ?
C13B C12B H12B 120.0 . . ?
C11 C12B H12B 120.0 . . ?
C12A C13A C14 119.78(14) . . ?
C12A C13A H13A 120.1 . . ?
C14 C13A H13A 120.1 . . ?
C14 C13B C12B 119.79(14) . . ?
C14 C13B H13B 120.1 . . ?
C12B C13B H13B 120.1 . . ?
C13B C14 C13A 120.38(13) . . ?
C13B C14 H14 119.8 . . ?
C13A C14 H14 119.8 . . ?
C1 N1 C8 120.26(12) . . ?
C1 N1 C10 120.83(12) . . ?
C8 N1 C10 118.54(12) . . ?
C2 O1 H1 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
N1 C1 C2 O1 179.20(12) . . . . ?
C11 C1 C2 O1 0.9(2) . . . . ?
N1 C1 C2 C3 1.4(2) . . . . ?
C11 C1 C2 C3 -176.94(13) . . . . ?
O1 C2 C3 O2 3.0(2) . . . . ?
C1 C2 C3 O2 -179.12(15) . . . . ?
O1 C2 C3 C9 -174.75(12) . . . . ?
C1 C2 C3 C9 3.1(2) . . . . ?
C9 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 N1 179.93(13) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
N1 C8 C9 C4 179.94(12) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
N1 C8 C9 C3 -0.1(2) . . . . ?
C7 C8 C9 C3 179.20(12) . . . . ?
C5 C4 C9 C8 0.3(2) . . . . ?
C5 C4 C9 C3 -179.68(13) . . . . ?
O2 C3 C9 C8 178.56(15) . . . . ?
C2 C3 C9 C8 -3.7(2) . . . . ?
O2 C3 C9 C4 -1.5(2) . . . . ?
C2 C3 C9 C4 176.29(13) . . . . ?
C2 C1 C11 C12A -65.1(2) . . . . ?
N1 C1 C11 C12A 116.58(15) . . . . ?
C2 C1 C11 C12B 114.12(17) . . . . ?
N1 C1 C11 C12B -64.23(19) . . . . ?
C12B C11 C12A C13A 2.3(2) . . . . ?
C1 C11 C12A C13A -178.51(13) . . . . ?
C12A C11 C12B C13B -2.1(2) . . . . ?
C1 C11 C12B C13B 178.73(13) . . . . ?
C11 C12A C13A C14 -0.3(2) . . . . ?
C11 C12B C13B C14 -0.1(2) . . . . ?
C12B C13B C14 C13A 2.1(2) . . . . ?
C12A C13A C14 C13B -1.8(2) . . . . ?
C2 C1 N1 C8 -5.4(2) . . . . ?
C11 C1 N1 C8 172.88(12) . . . . ?
C2 C1 N1 C10 167.39(14) . . . . ?
C11 C1 N1 C10 -14.3(2) . . . . ?
C9 C8 N1 C1 4.7(2) . . . . ?
C7 C8 N1 C1 -174.53(12) . . . . ?
C9 C8 N1 C10 -168.26(13) . . . . ?
C7 C8 N1 C10 12.5(2) . . . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

