# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_j5_1731
_database_code_depnum_ccdc_archive 'CCDC 1448109'
_audit_update_record             
;
2016-01-18 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_date             2016-01-17T00:02:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21 H17 N1 O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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                   10.9312(6)
_cell_length_b                   9.1547(9)
_cell_length_c                   16.4772(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.129(5)
_cell_angle_gamma                90
_cell_volume                     1646.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    877
_cell_measurement_theta_min      3.721
_cell_measurement_theta_max      21.593
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0.0
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.1288
_diffrn_reflns_number            7529
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.904
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3006
_reflns_number_gt                1571
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    SIR92
_computing_molecular_graphics    MERCURY
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1946
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.6930(3) 0.6860(4) 0.4074(2) 0.0399(10) Uani 1 1 d . . . . .
C2 C 0.7482(3) 0.6630(4) 0.3347(2) 0.0425(10) Uani 1 1 d . . . . .
H2 H 0.8293 0.6904 0.3292 0.051 Uiso 1 1 calc R U . . .
C3 C 0.6824(3) 0.5999(4) 0.2710(2) 0.0431(11) Uani 1 1 d . . . . .
H3 H 0.7207 0.5849 0.2227 0.052 Uiso 1 1 calc R U . . .
C4 C 0.5610(3) 0.5571(4) 0.2753(2) 0.0407(10) Uani 1 1 d . . . . .
C5 C 0.5092(3) 0.5799(5) 0.3493(2) 0.0526(12) Uani 1 1 d . . . . .
H5 H 0.4282 0.5522 0.3549 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5733(3) 0.6417(5) 0.4141(2) 0.0519(12) Uani 1 1 d . . . . .
H6 H 0.5359 0.654 0.4631 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4888(3) 0.4934(4) 0.2081(2) 0.0443(11) Uani 1 1 d . . . . .
H7 H 0.4054 0.4838 0.2153 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5270(3) 0.4468(4) 0.1375(2) 0.0415(10) Uani 1 1 d . . . . .
H8 H 0.6096 0.4585 0.1281 0.05 Uiso 1 1 calc R U . . .
C9 C 0.4488(3) 0.3785(4) 0.0734(2) 0.0363(10) Uani 1 1 d . . . . .
C10 C 0.4388(3) 0.2182(4) -0.0366(2) 0.0381(10) Uani 1 1 d . . . . .
C11 C 0.5065(3) 0.1228(4) -0.0892(2) 0.0453(11) Uani 1 1 d . . . . .
H11 H 0.578 0.0806 -0.0668 0.054 Uiso 1 1 calc R U . . .
C12 C 0.4753(3) 0.0909(4) -0.1657(2) 0.0471(11) Uani 1 1 d . . . . .
H12 H 0.4043 0.1346 -0.1877 0.056 Uiso 1 1 calc R U . . .
C13 C 0.5402(3) -0.0056(4) -0.2198(2) 0.0395(10) Uani 1 1 d . . . . .
C14 C 0.5054(3) -0.0131(5) -0.3018(2) 0.0494(12) Uani 1 1 d . . . . .
H14 H 0.4423 0.0466 -0.3225 0.059 Uiso 1 1 calc R U . . .
C15 C 0.5619(3) -0.1068(5) -0.3539(2) 0.0525(12) Uani 1 1 d . . . . .
H15 H 0.5365 -0.11 -0.4087 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6558(3) -0.1954(5) -0.3243(2) 0.0456(11) Uani 1 1 d . . . . .
C17 C 0.6929(3) -0.1870(5) -0.2432(2) 0.0476(11) Uani 1 1 d . . . . .
H17A H 0.7576 -0.2449 -0.2231 0.057 Uiso 1 1 calc R U . . .
C18 C 0.6362(3) -0.0949(4) -0.1919(2) 0.0438(10) Uani 1 1 d . . . . .
H18 H 0.6625 -0.0919 -0.1373 0.053 Uiso 1 1 calc R U . . .
C19 C 0.3130(3) 0.2372(4) -0.0471(2) 0.0492(11) Uani 1 1 d . . . . .
H19 H 0.2677 0.1866 -0.0874 0.059 Uiso 1 1 calc R U . . .
C20 C 0.2569(3) 0.3328(5) 0.0035(2) 0.0547(12) Uani 1 1 d . . . . .
H20 H 0.1728 0.348 -0.0028 0.066 Uiso 1 1 calc R U . . .
C21 C 0.3244(3) 0.4059(4) 0.0633(2) 0.0493(11) Uani 1 1 d . . . . .
H21 H 0.2872 0.4728 0.0965 0.059 Uiso 1 1 calc R U . . .
N1 N 0.5054(2) 0.2876(3) 0.02297(17) 0.0356(8) Uani 1 1 d . . . . .
O1 O 0.75066(19) 0.7535(3) 0.47201(13) 0.0549(9) Uani 1 1 d . . . . .
H1 H 0.8315 0.7609 0.4706 0.082 Uiso 1 1 d R U . . .
O2 O 0.7132(2) -0.2936(3) -0.37038(16) 0.0694(9) Uani 1 1 d . . . . .
H2A H 0.7114 -0.2649 -0.4236 0.104 Uiso 1 1 d R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O1 1.357(4) . ?
C1 C6 1.380(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.367(4) . ?
C2 H2 0.93 . ?
C3 C4 1.389(4) . ?
C3 H3 0.93 . ?
C4 C5 1.388(4) . ?
C4 C7 1.446(4) . ?
C5 C6 1.369(5) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.327(4) . ?
C7 H7 0.93 . ?
C8 C9 1.463(5) . ?
C8 H8 0.93 . ?
C9 N1 1.349(4) . ?
C9 C21 1.383(4) . ?
C10 N1 1.348(4) . ?
C10 C19 1.388(4) . ?
C10 C11 1.459(5) . ?
C11 C12 1.321(4) . ?
C11 H11 0.93 . ?
C12 C13 1.465(5) . ?
C12 H12 0.93 . ?
C13 C14 1.386(4) . ?
C13 C18 1.389(4) . ?
C14 C15 1.382(5) . ?
C14 H14 0.93 . ?
C15 C16 1.377(5) . ?
C15 H15 0.93 . ?
C16 O2 1.353(4) . ?
C16 C17 1.377(5) . ?
C17 C18 1.367(5) . ?
C17 H17A 0.93 . ?
C18 H18 0.93 . ?
C19 C20 1.376(5) . ?
C19 H19 0.93 . ?
C20 C21 1.372(5) . ?
C20 H20 0.93 . ?
C21 H21 0.93 . ?
O1 H1 0.8881 . ?
O2 H2A 0.9143 . ?

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
O1 C1 C6 118.2(3) . . ?
O1 C1 C2 122.8(3) . . ?
C6 C1 C2 119.0(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 123.0(3) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C3 116.0(3) . . ?
C5 C4 C7 120.1(3) . . ?
C3 C4 C7 123.9(3) . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C4 128.0(3) . . ?
C8 C7 H7 116 . . ?
C4 C7 H7 116 . . ?
C7 C8 C9 124.8(3) . . ?
C7 C8 H8 117.6 . . ?
C9 C8 H8 117.6 . . ?
N1 C9 C21 121.2(3) . . ?
N1 C9 C8 116.0(3) . . ?
C21 C9 C8 122.8(3) . . ?
N1 C10 C19 121.5(3) . . ?
N1 C10 C11 116.4(3) . . ?
C19 C10 C11 122.1(3) . . ?
C12 C11 C10 126.0(4) . . ?
C12 C11 H11 117 . . ?
C10 C11 H11 117 . . ?
C11 C12 C13 127.3(4) . . ?
C11 C12 H12 116.3 . . ?
C13 C12 H12 116.3 . . ?
C14 C13 C18 117.1(3) . . ?
C14 C13 C12 120.5(4) . . ?
C18 C13 C12 122.4(3) . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
O2 C16 C17 117.4(4) . . ?
O2 C16 C15 123.5(3) . . ?
C17 C16 C15 119.1(4) . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C17 C18 C13 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C20 C19 C10 118.4(4) . . ?
C20 C19 H19 120.8 . . ?
C10 C19 H19 120.8 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C9 119.0(4) . . ?
C20 C21 H21 120.5 . . ?
C9 C21 H21 120.5 . . ?
C10 N1 C9 119.4(3) . . ?
C1 O1 H1 115.8 . . ?
C16 O2 H2A 111.1 . . ?

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 -177.1(4) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C7 178.4(4) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C7 C4 C5 C6 -179.0(4) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
O1 C1 C6 C5 176.6(4) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C5 C4 C7 C8 -170.5(4) . . . . ?
C3 C4 C7 C8 10.1(7) . . . . ?
C4 C7 C8 C9 177.7(4) . . . . ?
C7 C8 C9 N1 -154.1(4) . . . . ?
C7 C8 C9 C21 26.9(6) . . . . ?
N1 C10 C11 C12 -151.7(4) . . . . ?
C19 C10 C11 C12 28.0(6) . . . . ?
C10 C11 C12 C13 -179.2(4) . . . . ?
C11 C12 C13 C14 -171.3(4) . . . . ?
C11 C12 C13 C18 10.1(6) . . . . ?
C18 C13 C14 C15 1.1(6) . . . . ?
C12 C13 C14 C15 -177.7(4) . . . . ?
C13 C14 C15 C16 -0.2(6) . . . . ?
C14 C15 C16 O2 177.7(4) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
O2 C16 C17 C18 -177.3(4) . . . . ?
C15 C16 C17 C18 1.5(6) . . . . ?
C16 C17 C18 C13 -0.7(6) . . . . ?
C14 C13 C18 C17 -0.6(6) . . . . ?
C12 C13 C18 C17 178.1(3) . . . . ?
N1 C10 C19 C20 1.8(5) . . . . ?
C11 C10 C19 C20 -177.9(4) . . . . ?
C10 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C9 -2.0(6) . . . . ?
N1 C9 C21 C20 3.6(5) . . . . ?
C8 C9 C21 C20 -177.5(4) . . . . ?
C19 C10 N1 C9 -0.3(5) . . . . ?
C11 C10 N1 C9 179.4(3) . . . . ?
C21 C9 N1 C10 -2.4(5) . . . . ?
C8 C9 N1 C10 178.6(3) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


