# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_k14phar1
_database_code_depnum_ccdc_archive 'CCDC 1408401'
_audit_update_record             
;
2015-07-03 deposited with the CCDC.
2015-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26

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                   7.9496(2)
_cell_length_b                   8.5205(2)
_cell_length_c                   9.6732(2)
_cell_angle_alpha                108.9192(9)
_cell_angle_beta                 98.7190(10)
_cell_angle_gamma                103.0474(10)
_cell_volume                     585.57(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8615
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      30.034

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       '280 2.0 degree images with \v scans'
_diffrn_reflns_number            13540
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.732
_diffrn_reflns_theta_max         30.062
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3395
_reflns_number_gt                2641
_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       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL-2013 (Sheldrick, 2013)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_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)+(0.0699P)²+0.1060P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.85686(14) 0.16541(12) 0.22573(10) 0.0270(2) Uani 1 1 d . . . . .
H1 H 0.906(2) 0.271(2) 0.2294(17) 0.038(4) Uiso 1 1 d . . . . .
O1 O 0.48572(11) -0.28812(10) 0.15812(9) 0.0316(2) Uani 1 1 d . . . . .
O2 O 0.63978(11) 0.27538(12) 0.59791(10) 0.0363(2) Uani 1 1 d . . . . .
H2 H 0.604(3) 0.292(2) 0.689(2) 0.056(5) Uiso 1 1 d . . . . .
C1 C 0.60562(15) -0.15668(14) 0.17792(12) 0.0252(2) Uani 1 1 d . . . . .
C2 C 0.66338(14) -0.11783(14) 0.05343(12) 0.0249(2) Uani 1 1 d . . . . .
C3 C 0.60342(15) -0.24357(17) -0.09388(13) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.5254 -0.3543 -0.1117 0.039 Uiso 1 1 calc R U . . .
C4 C 0.65601(16) -0.20849(18) -0.21229(13) 0.0355(3) Uani 1 1 d . . . . .
H4 H 0.6157 -0.2943 -0.3114 0.043 Uiso 1 1 calc R U . . .
C5 C 0.77010(17) -0.04412(18) -0.18468(13) 0.0329(3) Uani 1 1 d . . . . .
H5 H 0.8036 -0.0177 -0.2666 0.039 Uiso 1 1 calc R U . . .
C6 C 0.83448(17) 0.07948(16) -0.04120(13) 0.0304(3) Uani 1 1 d . . . . .
H6 H 0.9136 0.1892 -0.0248 0.037 Uiso 1 1 calc R U . . .
C7 C 0.78380(15) 0.04445(14) 0.08180(12) 0.0244(2) Uani 1 1 d . . . . .
C8 C 0.76888(15) 0.15762(14) 0.34596(12) 0.0239(2) Uani 1 1 d . . . . .
H8 H 0.6619 0.1996 0.3338 0.029 Uiso 1 1 calc R U . . .
C9 C 0.89276(14) 0.26880(13) 0.49926(11) 0.0223(2) Uani 1 1 d . . . . .
C10 C 1.07698(15) 0.31574(14) 0.52200(12) 0.0259(2) Uani 1 1 d . . . . .
H10 H 1.1275 0.2853 0.4377 0.031 Uiso 1 1 calc R U . . .
C11 C 1.18892(16) 0.40628(14) 0.66554(14) 0.0297(3) Uani 1 1 d . . . . .
H11 H 1.3144 0.4387 0.6787 0.036 Uiso 1 1 calc R U . . .
C12 C 1.11593(16) 0.44892(14) 0.78923(13) 0.0298(3) Uani 1 1 d . . . . .
H12 H 1.1916 0.5064 0.8879 0.036 Uiso 1 1 calc R U . . .
C13 C 0.93227(17) 0.40755(15) 0.76886(13) 0.0290(3) Uani 1 1 d . . . . .
H13 H 0.8826 0.4401 0.8534 0.035 Uiso 1 1 calc R U . . .
C14 C 0.82039(15) 0.31815(14) 0.62418(12) 0.0254(2) Uani 1 1 d . . . . .
C15 C 0.70955(16) -0.03148(14) 0.33392(12) 0.0272(2) Uani 1 1 d . . . . .
H15A H 0.8162 -0.0660 0.3635 0.033 Uiso 1 1 calc R U . . .
H15B H 0.6350 -0.0399 0.4060 0.033 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 C7 1.3755(14) . ?
N1 C8 1.4566(14) . ?
N1 H1 0.884(17) . ?
O1 C1 1.2341(14) . ?
O2 C14 1.3608(14) . ?
O2 H2 0.95(2) . ?
C1 C2 1.4588(16) . ?
C1 C15 1.5093(14) . ?
C2 C3 1.4068(15) . ?
C2 C7 1.4072(16) . ?
C3 C4 1.3736(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4021(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3751(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4101(16) . ?
C6 H6 0.9500 . ?
C8 C9 1.5137(14) . ?
C8 C15 1.5332(15) . ?
C8 H8 1.0000 . ?
C9 C10 1.3906(15) . ?
C9 C14 1.3995(15) . ?
C10 C11 1.3913(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3870(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3892(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3983(15) . ?
C13 H13 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C7 N1 C8 120.02(9) . . ?
C7 N1 H1 113.9(10) . . ?
C8 N1 H1 115.1(10) . . ?
C14 O2 H2 110.7(11) . . ?
O1 C1 C2 122.52(10) . . ?
O1 C1 C15 121.62(10) . . ?
C2 C1 C15 115.76(9) . . ?
C3 C2 C7 119.93(10) . . ?
C3 C2 C1 120.32(10) . . ?
C7 C2 C1 119.73(9) . . ?
C4 C3 C2 120.94(12) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.99(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 121.22(11) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.42(11) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C7 C2 121.70(10) . . ?
N1 C7 C6 119.84(10) . . ?
C2 C7 C6 118.42(10) . . ?
N1 C8 C9 111.15(9) . . ?
N1 C8 C15 108.70(9) . . ?
C9 C8 C15 109.39(9) . . ?
N1 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C15 C8 H8 109.2 . . ?
C10 C9 C14 118.59(9) . . ?
C10 C9 C8 122.25(10) . . ?
C14 C9 C8 119.05(10) . . ?
C9 C10 C11 121.42(10) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 119.53(11) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.03(10) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.16(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
O2 C14 C13 122.53(10) . . ?
O2 C14 C9 117.28(9) . . ?
C13 C14 C9 120.19(10) . . ?
C1 C15 C8 113.40(9) . . ?
C1 C15 H15A 108.9 . . ?
C8 C15 H15A 108.9 . . ?
C1 C15 H15B 108.9 . . ?
C8 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?

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 C1 C2 C3 -10.27(18) . . . . ?
C15 C1 C2 C3 166.05(11) . . . . ?
O1 C1 C2 C7 171.63(11) . . . . ?
C15 C1 C2 C7 -12.06(16) . . . . ?
C7 C2 C3 C4 -2.22(18) . . . . ?
C1 C2 C3 C4 179.67(11) . . . . ?
C2 C3 C4 C5 -0.45(19) . . . . ?
C3 C4 C5 C6 2.24(19) . . . . ?
C4 C5 C6 C7 -1.30(19) . . . . ?
C8 N1 C7 C2 -21.64(16) . . . . ?
C8 N1 C7 C6 160.72(10) . . . . ?
C3 C2 C7 N1 -174.56(11) . . . . ?
C1 C2 C7 N1 3.55(17) . . . . ?
C3 C2 C7 C6 3.11(17) . . . . ?
C1 C2 C7 C6 -178.78(10) . . . . ?
C5 C6 C7 N1 176.34(11) . . . . ?
C5 C6 C7 C2 -1.38(17) . . . . ?
C7 N1 C8 C9 164.75(9) . . . . ?
C7 N1 C8 C15 44.30(14) . . . . ?
N1 C8 C9 C10 -22.06(14) . . . . ?
C15 C8 C9 C10 97.98(12) . . . . ?
N1 C8 C9 C14 161.64(10) . . . . ?
C15 C8 C9 C14 -78.33(12) . . . . ?
C14 C9 C10 C11 1.50(16) . . . . ?
C8 C9 C10 C11 -174.82(10) . . . . ?
C9 C10 C11 C12 0.88(17) . . . . ?
C10 C11 C12 C13 -2.63(18) . . . . ?
C11 C12 C13 C14 1.97(17) . . . . ?
C12 C13 C14 O2 -179.60(11) . . . . ?
C12 C13 C14 C9 0.46(17) . . . . ?
C10 C9 C14 O2 177.89(10) . . . . ?
C8 C9 C14 O2 -5.67(15) . . . . ?
C10 C9 C14 C13 -2.16(16) . . . . ?
C8 C9 C14 C13 174.28(10) . . . . ?
O1 C1 C15 C8 -147.25(11) . . . . ?
C2 C1 C15 C8 36.40(14) . . . . ?
N1 C8 C15 C1 -50.66(13) . . . . ?
C9 C8 C15 C1 -172.19(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.95(2) 1.74(2) 2.6783(12) 170.4(17) 2_656
C15 H15B O2 0.99 2.60 3.3621(14) 134.1 2_656

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
