# 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_ertan39_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1456335'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;

_audit_creation_date             2016-02-26T17:17:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.3

#----------------------------------------------------------------------------#
#                   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                   4.7369(4)
_cell_length_b                   24.686(2)
_cell_length_c                   12.2902(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.492(3)
_cell_angle_gamma                90
_cell_volume                     1417.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      24.83


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

_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             600
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.11
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.16

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_av_R_equivalents  0.0974
_diffrn_reflns_number            56958
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             3508
_reflns_number_gt                1973
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_device_type  'rigaku R-axis rapid S'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?



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

_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_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)+(0.0584P)²+0.2554P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.017(2)
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.112
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1014
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3538(2) 0.45404(4) 0.32885(9) 0.0486(3) Uani 1 d . .
O2 O 0.6997(3) 0.42796(5) 0.05219(10) 0.0656(4) Uani 1 d . .
N1 N 0.6551(3) 0.40526(5) 0.22836(10) 0.0421(3) Uani 1 d . .
N2 N 0.8395(3) 0.36213(5) 0.24043(11) 0.0473(4) Uani 1 d . .
C7 C 0.2785(3) 0.48675(6) 0.23793(12) 0.0389(4) Uani 1 d . .
C1 C 0.0776(3) 0.52945(6) 0.25859(13) 0.0401(4) Uani 1 d . .
C10 C 0.5413(3) 0.41338(6) 0.32139(13) 0.0423(4) Uani 1 d . .
C8 C 0.3858(3) 0.47869(6) 0.14566(13) 0.0433(4) Uani 1 d . .
H8 H 0.3263 0.5015 0.086 0.052 Uiso 1 calc . .
C9 C 0.5889(4) 0.43663(6) 0.13315(13) 0.0450(4) Uani 1 d . .
C12 C 0.8312(3) 0.34438(6) 0.34207(13) 0.0458(4) Uani 1 d . .
C11 C 0.6475(4) 0.37536(7) 0.39664(14) 0.0510(4) Uani 1 d . .
H11 H 0.6082 0.3708 0.4678 0.061 Uiso 1 calc . .
C2 C -0.0481(4) 0.56316(7) 0.17351(14) 0.0496(4) Uani 1 d . .
H2 H -0.0047 0.5587 0.103 0.059 Uiso 1 calc . .
C13 C 0.9984(3) 0.29637(7) 0.38435(15) 0.0500(4) Uani 1 d . .
C6 C 0.0106(4) 0.53734(8) 0.36260(15) 0.0573(5) Uani 1 d . .
H6 H 0.0921 0.5151 0.4204 0.069 Uiso 1 calc . .
C3 C -0.2370(4) 0.60319(7) 0.19331(16) 0.0560(5) Uani 1 d . .
H3 H -0.3217 0.6253 0.1358 0.067 Uiso 1 calc . .
C4 C -0.3003(4) 0.61048(8) 0.29688(17) 0.0621(5) Uani 1 d . .
H4 H -0.4274 0.6375 0.3099 0.075 Uiso 1 calc . .
C18 C 1.1606(4) 0.26854(7) 0.31901(18) 0.0650(5) Uani 1 d . .
H18 H 1.1682 0.2807 0.2479 0.078 Uiso 1 calc . .
C14 C 0.9923(4) 0.27766(8) 0.48994(18) 0.0700(6) Uani 1 d . .
H14 H 0.8857 0.296 0.5354 0.084 Uiso 1 calc . .
C5 C -0.1757(4) 0.57776(9) 0.38159(18) 0.0710(6) Uani 1 d . .
H5 H -0.2172 0.5829 0.4522 0.085 Uiso 1 calc . .
C16 C 1.3029(5) 0.20435(9) 0.4632(2) 0.0849(8) Uani 1 d . .
H16 H 1.4045 0.1735 0.4895 0.102 Uiso 1 calc . .
C17 C 1.3115(5) 0.22282(8) 0.3585(2) 0.0817(7) Uani 1 d . .
H17 H 1.4197 0.2044 0.3138 0.098 Uiso 1 calc . .
C15 C 1.1447(5) 0.23158(10) 0.5284(2) 0.0850(7) Uani 1 d . .
H15 H 1.1386 0.2192 0.5994 0.102 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   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
O1 C10 1.3534(19) . ?
O1 C7 1.3771(17) . ?
O2 C9 1.2179(19) . ?
N1 C10 1.357(2) . ?
N1 N2 1.3696(17) . ?
N1 C9 1.395(2) . ?
N2 C12 1.331(2) . ?
C7 C8 1.332(2) . ?
C7 C1 1.470(2) . ?
C1 C6 1.381(2) . ?
C1 C2 1.391(2) . ?
C10 C11 1.355(2) . ?
C8 C9 1.441(2) . ?
C8 H8 0.93 . ?
C12 C11 1.409(2) . ?
C12 C13 1.472(2) . ?
C11 H11 0.93 . ?
C2 C3 1.381(2) . ?
C2 H2 0.93 . ?
C13 C14 1.382(3) . ?
C13 C18 1.383(3) . ?
C6 C5 1.377(3) . ?
C6 H6 0.93 . ?
C3 C4 1.367(3) . ?
C3 H3 0.93 . ?
C4 C5 1.372(3) . ?
C4 H4 0.93 . ?
C18 C17 1.381(3) . ?
C18 H18 0.93 . ?
C14 C15 1.388(3) . ?
C14 H14 0.93 . ?
C5 H5 0.93 . ?
C16 C15 1.361(3) . ?
C16 C17 1.372(3) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
C15 H15 0.93 . ?

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
C10 O1 C7 117.71(12) . . ?
C10 N1 N2 111.00(12) . . ?
C10 N1 C9 124.00(13) . . ?
N2 N1 C9 125.00(13) . . ?
C12 N2 N1 103.93(13) . . ?
C8 C7 O1 121.28(14) . . ?
C8 C7 C1 127.08(14) . . ?
O1 C7 C1 111.63(13) . . ?
C6 C1 C2 118.45(15) . . ?
C6 C1 C7 121.01(14) . . ?
C2 C1 C7 120.53(14) . . ?
O1 C10 C11 129.90(15) . . ?
O1 C10 N1 121.52(13) . . ?
C11 C10 N1 108.58(14) . . ?
C7 C8 C9 123.62(14) . . ?
C7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
O2 C9 N1 121.34(15) . . ?
O2 C9 C8 126.80(15) . . ?
N1 C9 C8 111.85(14) . . ?
N2 C12 C11 112.61(14) . . ?
N2 C12 C13 119.95(15) . . ?
C11 C12 C13 127.42(15) . . ?
C10 C11 C12 103.89(15) . . ?
C10 C11 H11 128.1 . . ?
C12 C11 H11 128.1 . . ?
C3 C2 C1 120.32(17) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C14 C13 C18 118.62(17) . . ?
C14 C13 C12 120.49(17) . . ?
C18 C13 C12 120.89(17) . . ?
C5 C6 C1 120.70(17) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C4 C3 C2 120.41(17) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.74(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C17 C18 C13 120.5(2) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C13 C14 C15 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C4 C5 C6 120.36(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C15 C16 C17 119.5(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?

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
C10 N1 N2 C12 0.58(17) . . . . ?
C9 N1 N2 C12 -178.77(14) . . . . ?
C10 O1 C7 C8 0.1(2) . . . . ?
C10 O1 C7 C1 -179.16(12) . . . . ?
C8 C7 C1 C6 -171.90(16) . . . . ?
O1 C7 C1 C6 7.3(2) . . . . ?
C8 C7 C1 C2 7.6(2) . . . . ?
O1 C7 C1 C2 -173.12(13) . . . . ?
C7 O1 C10 C11 -179.07(16) . . . . ?
C7 O1 C10 N1 0.9(2) . . . . ?
N2 N1 C10 O1 179.67(13) . . . . ?
C9 N1 C10 O1 -1.0(2) . . . . ?
N2 N1 C10 C11 -0.40(18) . . . . ?
C9 N1 C10 C11 178.95(15) . . . . ?
O1 C7 C8 C9 -1.0(2) . . . . ?
C1 C7 C8 C9 178.15(14) . . . . ?
C10 N1 C9 O2 179.22(15) . . . . ?
N2 N1 C9 O2 -1.5(2) . . . . ?
C10 N1 C9 C8 0.1(2) . . . . ?
N2 N1 C9 C8 179.38(13) . . . . ?
C7 C8 C9 O2 -178.18(17) . . . . ?
C7 C8 C9 N1 0.9(2) . . . . ?
N1 N2 C12 C11 -0.55(18) . . . . ?
N1 N2 C12 C13 178.05(13) . . . . ?
O1 C10 C11 C12 179.98(16) . . . . ?
N1 C10 C11 C12 0.05(18) . . . . ?
N2 C12 C11 C10 0.33(19) . . . . ?
C13 C12 C11 C10 -178.15(15) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C7 C1 C2 C3 179.93(14) . . . . ?
N2 C12 C13 C14 179.77(16) . . . . ?
C11 C12 C13 C14 -1.9(3) . . . . ?
N2 C12 C13 C18 -1.3(2) . . . . ?
C11 C12 C13 C18 177.07(17) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C7 C1 C6 C5 179.36(16) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C12 C13 C18 C17 -178.50(17) . . . . ?
C18 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C15 178.39(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C1 C6 C5 C4 0.8(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C13 C18 C17 C16 -0.1(3) . . . . ?
C17 C16 C15 C14 0.0(4) . . . . ?
C13 C14 C15 C16 0.3(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
