# 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_exp_284_3
_database_code_depnum_ccdc_archive 'CCDC 1406726'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-26T14:30:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_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'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
_cell_length_a                   15.3324(6)
_cell_length_b                   5.1202(2)
_cell_length_c                   18.0418(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.979(4)
_cell_angle_gamma                90
_cell_volume                     1416.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3100
_cell_measurement_theta_min      4.1090
_cell_measurement_theta_max      25.3180

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

_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_min  0.84492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_number            5582
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.459
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_ful 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             2585
_reflns_number_gt                2294
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0399P)²+0.8751P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2585
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1044
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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'

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
C3 C 0.60756(10) 0.4966(3) 0.79679(9) 0.0200(3) Uani 1 d . .
C4 C 0.60206(10) 0.4291(3) 0.87356(9) 0.0197(3) Uani 1 d . .
C5 C 0.53994(10) 0.2275(3) 0.87402(8) 0.0193(3) Uani 1 d . .
C11 C 0.45197(10) -0.0034(3) 0.77535(9) 0.0210(4) Uani 1 d . .
C12 C 0.42871(12) 0.0091(3) 0.70068(10) 0.0279(4) Uani 1 d . .
H12 H 0.4538 0.1377 0.6696 0.033 Uiso 1 calc . .
C13 C 0.36853(12) -0.1678(4) 0.67190(10) 0.0333(4) Uani 1 d . .
H13 H 0.3529 -0.1608 0.6208 0.04 Uiso 1 calc . .
C14 C 0.33093(11) -0.3545(3) 0.71684(10) 0.0301(4) Uani 1 d . .
H14 H 0.2895 -0.4742 0.6968 0.036 Uiso 1 calc . .
C15 C 0.35442(11) -0.3645(3) 0.79103(10) 0.0269(4) Uani 1 d . .
H15 H 0.3287 -0.492 0.8221 0.032 Uiso 1 calc . .
C16 C 0.41513(10) -0.1908(3) 0.82092(9) 0.0236(4) Uani 1 d . .
H16 H 0.4313 -0.2 0.8719 0.028 Uiso 1 calc . .
C31 C 0.65663(11) 0.7122(3) 0.75979(9) 0.0237(4) Uani 1 d . .
H31A H 0.7153 0.6513 0.7479 0.036 Uiso 1 calc . .
H31B H 0.6609 0.8626 0.7932 0.036 Uiso 1 calc . .
H31C H 0.6257 0.7636 0.7141 0.036 Uiso 1 calc . .
C41 C 0.63573(10) 0.5224(3) 0.94364(9) 0.0208(3) Uani 1 d . .
C42 C 0.70818(10) 0.7122(3) 0.95156(9) 0.0204(3) Uani 1 d . .
C43 C 0.77925(10) 0.7126(3) 0.90438(9) 0.0234(4) Uani 1 d . .
H43 H 0.7809 0.593 0.8642 0.028 Uiso 1 calc . .
C44 C 0.84751(10) 0.8861(3) 0.91581(9) 0.0244(4) Uani 1 d . .
H44 H 0.8957 0.8831 0.8834 0.029 Uiso 1 calc . .
C45 C 0.84665(10) 1.0648(3) 0.97386(9) 0.0234(4) Uani 1 d . .
C46 C 0.77529(11) 1.0629(3) 1.02090(9) 0.0254(4) Uani 1 d . .
H46 H 0.7731 1.1845 1.0606 0.031 Uiso 1 calc . .
C47 C 0.70781(10) 0.8871(3) 1.01069(9) 0.0231(4) Uani 1 d . .
H47 H 0.6608 0.8855 1.0443 0.028 Uiso 1 calc . .
C48 C 0.92079(12) 1.2540(4) 0.98648(11) 0.0332(4) Uani 1 d . .
H48A H 0.9559 1.1978 1.0295 0.05 Uiso 1 calc . .
H48B H 0.8973 1.4288 0.9956 0.05 Uiso 1 calc . .
H48C H 0.9574 1.2584 0.9425 0.05 Uiso 1 calc . .
O5 O 0.50933(7) 0.1055(2) 0.93185(6) 0.0244(3) Uani 1 d . .
H5 H 0.5328 0.1659 0.9706 0.037 Uiso 1 calc . .
O41 O 0.60199(7) 0.4367(2) 1.00209(6) 0.0251(3) Uani 1 d . .
N1 N 0.51446(8) 0.1785(3) 0.80378(7) 0.0198(3) Uani 1 d . .
N2 N 0.55629(9) 0.3487(3) 0.75532(7) 0.0215(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.316(2) . ?
C3 C4 1.432(2) . ?
C3 C31 1.499(2) . ?
C4 C5 1.404(2) . ?
C4 C41 1.439(2) . ?
C5 O5 1.3100(19) . ?
C5 N1 1.343(2) . ?
C11 C12 1.389(2) . ?
C11 C16 1.390(2) . ?
C11 N1 1.425(2) . ?
C12 C13 1.388(3) . ?
C12 H12 0.95 . ?
C13 C14 1.385(3) . ?
C13 H13 0.95 . ?
C14 C15 1.381(3) . ?
C14 H14 0.95 . ?
C15 C16 1.390(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C41 O41 1.2615(19) . ?
C41 C42 1.481(2) . ?
C42 C47 1.393(2) . ?
C42 C43 1.394(2) . ?
C43 C44 1.386(2) . ?
C43 H43 0.95 . ?
C44 C45 1.391(2) . ?
C44 H44 0.95 . ?
C45 C46 1.396(2) . ?
C45 C48 1.508(2) . ?
C46 C47 1.381(2) . ?
C46 H46 0.95 . ?
C47 H47 0.95 . ?
C48 H48A 0.98 . ?
C48 H48B 0.98 . ?
C48 H48C 0.98 . ?
O5 H5 0.84 . ?
N1 N2 1.3980(18) . ?

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
N2 C3 C4 111.50(14) . . ?
N2 C3 C31 118.04(14) . . ?
C4 C3 C31 130.33(15) . . ?
C5 C4 C3 103.55(14) . . ?
C5 C4 C41 118.17(14) . . ?
C3 C4 C41 138.04(15) . . ?
O5 C5 N1 124.05(14) . . ?
O5 C5 C4 127.40(14) . . ?
N1 C5 C4 108.55(13) . . ?
C12 C11 C16 120.35(16) . . ?
C12 C11 N1 118.60(15) . . ?
C16 C11 N1 121.04(15) . . ?
C13 C12 C11 119.40(16) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.80(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.26(16) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.92(16) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 119.26(16) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 118.22(15) . . ?
O41 C41 C42 117.73(14) . . ?
C4 C41 C42 124.05(14) . . ?
C47 C42 C43 118.70(15) . . ?
C47 C42 C41 118.88(14) . . ?
C43 C42 C41 122.32(15) . . ?
C44 C43 C42 120.41(15) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 121.13(15) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C46 118.08(15) . . ?
C44 C45 C48 121.29(15) . . ?
C46 C45 C48 120.62(16) . . ?
C47 C46 C45 121.10(15) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C42 120.54(15) . . ?
C46 C47 H47 119.7 . . ?
C42 C47 H47 119.7 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C5 O5 H5 109.5 . . ?
C5 N1 N2 110.14(13) . . ?
C5 N1 C11 130.13(13) . . ?
N2 N1 C11 119.67(13) . . ?
C3 N2 N1 106.22(13) . . ?

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
N2 C3 C4 C5 -1.41(17) . . . . ?
C31 C3 C4 C5 174.34(16) . . . . ?
N2 C3 C4 C41 -175.29(18) . . . . ?
C31 C3 C4 C41 0.5(3) . . . . ?
C3 C4 C5 O5 -177.23(15) . . . . ?
C41 C4 C5 O5 -1.9(2) . . . . ?
C3 C4 C5 N1 1.87(17) . . . . ?
C41 C4 C5 N1 177.24(13) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
N1 C11 C12 C13 179.45(15) . . . . ?
C11 C12 C13 C14 0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
N1 C11 C16 C15 180.00(14) . . . . ?
C14 C15 C16 C11 0.5(2) . . . . ?
C5 C4 C41 O41 -6.6(2) . . . . ?
C3 C4 C41 O41 166.64(17) . . . . ?
C5 C4 C41 C42 172.97(14) . . . . ?
C3 C4 C41 C42 -13.8(3) . . . . ?
O41 C41 C42 C47 -33.2(2) . . . . ?
C4 C41 C42 C47 147.19(16) . . . . ?
O41 C41 C42 C43 143.09(16) . . . . ?
C4 C41 C42 C43 -36.5(2) . . . . ?
C47 C42 C43 C44 -0.8(2) . . . . ?
C41 C42 C43 C44 -177.11(15) . . . . ?
C42 C43 C44 C45 -0.5(2) . . . . ?
C43 C44 C45 C46 0.6(2) . . . . ?
C43 C44 C45 C48 180.00(15) . . . . ?
C44 C45 C46 C47 0.7(2) . . . . ?
C48 C45 C46 C47 -178.76(15) . . . . ?
C45 C46 C47 C42 -2.0(2) . . . . ?
C43 C42 C47 C46 2.0(2) . . . . ?
C41 C42 C47 C46 178.47(15) . . . . ?
O5 C5 N1 N2 177.39(13) . . . . ?
C4 C5 N1 N2 -1.75(17) . . . . ?
O5 C5 N1 C11 0.4(3) . . . . ?
C4 C5 N1 C11 -178.71(14) . . . . ?
C12 C11 N1 C5 171.18(16) . . . . ?
C16 C11 N1 C5 -9.2(2) . . . . ?
C12 C11 N1 N2 -5.5(2) . . . . ?
C16 C11 N1 N2 174.11(14) . . . . ?
C4 C3 N2 N1 0.41(17) . . . . ?
C31 C3 N2 N1 -175.92(13) . . . . ?
C5 N1 N2 C3 0.83(17) . . . . ?
C11 N1 N2 C3 178.16(13) . . . . ?
C3 C4 C41 C42 -13.8(3) . . . . ?
C4 C41 C42 C43 -36.5(2) . . . . ?
C5 N1 C11 C16 -9.2(2) . . . . ?

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
C16 H16 O5 0.95 2.24 2.880(2) 124.2 .
O5 H5 O41 0.84 1.83 2.5373(16) 140.8 .



####################################################################### 
# 
# 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_exp_1
_database_code_depnum_ccdc_archive 'CCDC 1406727'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-26T12:46:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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

loop_
_space_group_symop_operation_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'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
_cell_length_a                   15.3847(5)
_cell_length_b                   5.2035(2)
_cell_length_c                   18.2280(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.913(3)
_cell_angle_gamma                90
_cell_volume                     1459.04(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    4196
_cell_measurement_theta_min      2.8523
_cell_measurement_theta_max      29.4410

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

_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_number            11783
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.439
_diffrn_reflns_theta_max         29.506
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.88
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.88
_diffrn_reflns_point_group_measured_fraction_ful 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.88
_reflns_number_total             3580
_reflns_number_gt                2395
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0556P)²+0.4152P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3580
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   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'
O O 0.0106 0.006 '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'

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
C3 C 0.60945(11) 0.4897(3) 0.79776(9) 0.0402(4) Uani 1 d . .
C4 C 0.60347(10) 0.4250(3) 0.87385(9) 0.0394(4) Uani 1 d . .
C5 C 0.54115(11) 0.2264(4) 0.87446(9) 0.0402(4) Uani 1 d . .
C11 C 0.45419(11) -0.0013(4) 0.77648(10) 0.0426(4) Uani 1 d . .
C12 C 0.43109(14) 0.0109(4) 0.70282(11) 0.0596(5) Uani 1 d . .
H12 H 0.4558 0.1343 0.6727 0.072 Uiso 1 calc . .
C13 C 0.37089(16) -0.1620(5) 0.67428(13) 0.0724(7) Uani 1 d . .
H13 H 0.3556 -0.1545 0.6248 0.087 Uiso 1 calc . .
C14 C 0.33348(15) -0.3446(4) 0.71841(13) 0.0656(6) Uani 1 d . .
H14 H 0.2931 -0.4598 0.699 0.079 Uiso 1 calc . .
C15 C 0.35640(13) -0.3546(4) 0.79123(13) 0.0580(5) Uani 1 d . .
H15 H 0.331 -0.4771 0.8212 0.07 Uiso 1 calc . .
C16 C 0.41696(12) -0.1846(4) 0.82100(11) 0.0486(5) Uani 1 d . .
H16 H 0.4324 -0.194 0.8705 0.058 Uiso 1 calc . .
C31 C 0.65836(12) 0.7015(4) 0.76092(10) 0.0486(5) Uani 1 d . .
H31A H 0.7164 0.6448 0.751 0.073 Uiso 1 calc . .
H31B H 0.6606 0.8491 0.7925 0.073 Uiso 1 calc . .
H31C H 0.6294 0.7461 0.7157 0.073 Uiso 1 calc . .
C41 C 0.63690(11) 0.5177(4) 0.94277(10) 0.0419(4) Uani 1 d . .
C42 C 0.70860(11) 0.7053(4) 0.95116(9) 0.0412(4) Uani 1 d . .
C43 C 0.78005(11) 0.7078(4) 0.90543(10) 0.0472(5) Uani 1 d . .
H43 H 0.7827 0.5926 0.8665 0.057 Uiso 1 calc . .
C44 C 0.84715(12) 0.8802(4) 0.91729(11) 0.0519(5) Uani 1 d . .
H44 H 0.8946 0.8783 0.8863 0.062 Uiso 1 calc . .
C45 C 0.84524(12) 1.0556(4) 0.97437(11) 0.0501(5) Uani 1 d . .
C46 C 0.77401(13) 1.0511(4) 1.02005(11) 0.0543(5) Uani 1 d . .
H46 H 0.7711 1.1678 1.0586 0.065 Uiso 1 calc . .
C47 C 0.70747(12) 0.8773(4) 1.00941(10) 0.0487(5) Uani 1 d . .
H47 H 0.6612 0.8751 1.0416 0.058 Uiso 1 calc . .
C48 C 0.91821(15) 1.2468(5) 0.98696(14) 0.0743(7) Uani 1 d . .
H48A H 0.9525 1.1952 1.0289 0.111 Uiso 1 calc . .
H48B H 0.8941 1.4141 0.9955 0.111 Uiso 1 calc . .
H48C H 0.9542 1.2522 0.9445 0.111 Uiso 1 calc . .
O5 O 0.51047(9) 0.1072(3) 0.93129(7) 0.0522(4) Uani 1 d . .
H5 H 0.5287 0.1763 0.9689 0.078 Uiso 1 calc . .
O41 O 0.60327(8) 0.4323(3) 1.00123(7) 0.0532(4) Uani 1 d . .
N1 N 0.51641(9) 0.1770(3) 0.80471(8) 0.0412(4) Uani 1 d . .
N2 N 0.55862(9) 0.3440(3) 0.75687(8) 0.0439(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.313(2) . ?
C3 C4 1.432(2) . ?
C3 C31 1.499(2) . ?
C4 C5 1.410(2) . ?
C4 C41 1.434(2) . ?
C5 O5 1.303(2) . ?
C5 N1 1.346(2) . ?
C11 C16 1.383(3) . ?
C11 C12 1.385(3) . ?
C11 N1 1.423(2) . ?
C12 C13 1.387(3) . ?
C12 H12 0.93 . ?
C13 C14 1.377(3) . ?
C13 H13 0.93 . ?
C14 C15 1.369(3) . ?
C14 H14 0.93 . ?
C15 C16 1.389(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C41 O41 1.272(2) . ?
C41 C42 1.479(3) . ?
C42 C47 1.389(3) . ?
C42 C43 1.390(2) . ?
C43 C44 1.382(3) . ?
C43 H43 0.93 . ?
C44 C45 1.385(3) . ?
C44 H44 0.93 . ?
C45 C46 1.387(3) . ?
C45 C48 1.515(3) . ?
C46 C47 1.377(3) . ?
C46 H46 0.93 . ?
C47 H47 0.93 . ?
C48 H48A 0.96 . ?
C48 H48B 0.96 . ?
C48 H48C 0.96 . ?
O5 H5 0.82 . ?
N1 N2 1.3981(19) . ?

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
N2 C3 C4 111.55(15) . . ?
N2 C3 C31 117.96(15) . . ?
C4 C3 C31 130.34(17) . . ?
C5 C4 C3 103.55(15) . . ?
C5 C4 C41 118.32(16) . . ?
C3 C4 C41 137.91(17) . . ?
O5 C5 N1 124.02(16) . . ?
O5 C5 C4 127.64(16) . . ?
N1 C5 C4 108.34(15) . . ?
C16 C11 C12 119.90(18) . . ?
C16 C11 N1 121.34(16) . . ?
C12 C11 N1 118.77(17) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.3(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 119.45(19) . . ?
C11 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 118.12(16) . . ?
O41 C41 C42 117.17(16) . . ?
C4 C41 C42 124.71(16) . . ?
C47 C42 C43 118.15(17) . . ?
C47 C42 C41 119.07(16) . . ?
C43 C42 C41 122.68(16) . . ?
C44 C43 C42 120.54(18) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 121.37(18) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 H44 119.3 . . ?
C44 C45 C46 117.81(18) . . ?
C44 C45 C48 121.5(2) . . ?
C46 C45 C48 120.7(2) . . ?
C47 C46 C45 121.25(18) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C42 120.83(17) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C5 O5 H5 109.5 . . ?
C5 N1 N2 110.07(14) . . ?
C5 N1 C11 130.11(15) . . ?
N2 N1 C11 119.73(14) . . ?
C3 N2 N1 106.45(13) . . ?

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
N2 C3 C4 C5 -1.43(19) . . . . ?
C31 C3 C4 C5 173.96(18) . . . . ?
N2 C3 C4 C41 -175.57(19) . . . . ?
C31 C3 C4 C41 -0.2(3) . . . . ?
C3 C4 C5 O5 -177.57(17) . . . . ?
C41 C4 C5 O5 -2.0(3) . . . . ?
C3 C4 C5 N1 1.99(19) . . . . ?
C41 C4 C5 N1 177.54(15) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
N1 C11 C12 C13 179.70(19) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N1 C11 C16 C15 179.89(16) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C5 C4 C41 O41 -6.0(2) . . . . ?
C3 C4 C41 O41 167.52(19) . . . . ?
C5 C4 C41 C42 173.47(16) . . . . ?
C3 C4 C41 C42 -13.0(3) . . . . ?
O41 C41 C42 C47 -33.7(2) . . . . ?
C4 C41 C42 C47 146.83(18) . . . . ?
O41 C41 C42 C43 142.61(18) . . . . ?
C4 C41 C42 C43 -36.9(3) . . . . ?
C47 C42 C43 C44 -1.0(3) . . . . ?
C41 C42 C43 C44 -177.35(17) . . . . ?
C42 C43 C44 C45 -0.4(3) . . . . ?
C43 C44 C45 C46 0.7(3) . . . . ?
C43 C44 C45 C48 -179.27(19) . . . . ?
C44 C45 C46 C47 0.4(3) . . . . ?
C48 C45 C46 C47 -179.66(19) . . . . ?
C45 C46 C47 C42 -1.8(3) . . . . ?
C43 C42 C47 C46 2.1(3) . . . . ?
C41 C42 C47 C46 178.55(17) . . . . ?
O5 C5 N1 N2 177.65(16) . . . . ?
C4 C5 N1 N2 -1.93(19) . . . . ?
O5 C5 N1 C11 1.0(3) . . . . ?
C4 C5 N1 C11 -178.55(16) . . . . ?
C16 C11 N1 C5 -9.6(3) . . . . ?
C12 C11 N1 C5 170.52(19) . . . . ?
C16 C11 N1 N2 174.10(16) . . . . ?
C12 C11 N1 N2 -5.8(2) . . . . ?
C4 C3 N2 N1 0.32(19) . . . . ?
C31 C3 N2 N1 -175.70(15) . . . . ?
C5 N1 N2 C3 1.01(19) . . . . ?
C11 N1 N2 C3 178.03(15) . . . . ?
C3 C4 C41 C42 -13.0(3) . . . . ?
C4 C41 C42 C43 -36.9(3) . . . . ?
C5 N1 C11 C16 -9.6(3) . . . . ?

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
C16 H16 O5 0.93 2.26 2.885(2) 124.4 .
O5 H5 O41 0.82 1.85 2.5432(19) 141.7 .




####################################################################### 
# 
# 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_exp_311_lt
_database_code_depnum_ccdc_archive 'CCDC 1406728'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T16:29:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_cell_length_a                   11.7774(7)
_cell_length_b                   5.3159(16)
_cell_length_c                   23.349(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.592(7)
_cell_angle_gamma                90
_cell_volume                     1449.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)

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

_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_number            7186
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.637
_diffrn_reflns_theta_max         29.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.847
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_ful 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.847
_reflns_number_total             3308
_reflns_number_gt                2506
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0380P)²+1.0375P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
#                   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
C3 C 0.19256(14) 0.5186(4) 0.54949(7) 0.0232(4) Uani 1 d . .
C4 C 0.27518(14) 0.4424(4) 0.51277(7) 0.0231(4) Uani 1 d . .
C5 C 0.33577(13) 0.2482(4) 0.54370(7) 0.0225(4) Uani 1 d . .
C11 C 0.32403(14) 0.0365(4) 0.63923(7) 0.0228(4) Uani 1 d . .
C12 C 0.27829(15) 0.0648(4) 0.69111(8) 0.0284(4) Uani 1 d . .
H12 H 0.228 0.1959 0.6957 0.034 Uiso 1 calc . .
C13 C 0.30882(16) -0.1052(4) 0.73587(8) 0.0335(5) Uani 1 d . .
H13 H 0.2773 -0.089 0.7702 0.04 Uiso 1 calc . .
C14 C 0.38593(16) -0.2989(4) 0.72998(8) 0.0329(5) Uani 1 d . .
H14 H 0.4069 -0.4101 0.7603 0.039 Uiso 1 calc . .
C15 C 0.43118(15) -0.3240(4) 0.67823(8) 0.0299(4) Uani 1 d . .
H15 H 0.4827 -0.453 0.674 0.036 Uiso 1 calc . .
C16 C 0.40023(14) -0.1588(4) 0.63287(8) 0.0265(4) Uani 1 d . .
H16 H 0.4303 -0.1784 0.5983 0.032 Uiso 1 calc . .
C31 C 0.10916(14) 0.7338(4) 0.54352(8) 0.0268(4) Uani 1 d . .
H31A H 0.0426 0.6877 0.5173 0.04 Uiso 1 calc . .
H31B H 0.1446 0.8784 0.5288 0.04 Uiso 1 calc . .
H31C H 0.087 0.7728 0.5806 0.04 Uiso 1 calc . .
C41 C 0.31150(14) 0.5230(4) 0.45881(7) 0.0236(4) Uani 1 d . .
C42 C 0.24452(14) 0.7033(4) 0.41905(7) 0.0237(4) Uani 1 d . .
C47 C 0.30195(15) 0.8830(4) 0.38997(7) 0.0267(4) Uani 1 d . .
H47 H 0.3815 0.891 0.3962 0.032 Uiso 1 calc . .
C46 C 0.24083(16) 1.0491(4) 0.35193(8) 0.0291(4) Uani 1 d . .
H46 H 0.2799 1.171 0.3337 0.035 Uiso 1 calc . .
C45 C 0.12101(15) 1.0366(4) 0.34048(7) 0.0257(4) Uani 1 d . .
C44 C 0.06469(15) 0.8537(4) 0.36862(7) 0.0274(4) Uani 1 d . .
H44 H -0.0146 0.8409 0.3612 0.033 Uiso 1 calc . .
C43 C 0.12535(14) 0.6898(4) 0.40773(7) 0.0268(4) Uani 1 d . .
H43 H 0.0862 0.5701 0.4265 0.032 Uiso 1 calc . .
C48 C 0.05521(17) 1.2170(4) 0.29821(8) 0.0364(5) Uani 1 d . .
H48A H 0.0629 1.1664 0.2594 0.055 Uiso 1 calc . .
H48B H 0.0853 1.3838 0.3049 0.055 Uiso 1 calc . .
H48C H -0.0242 1.2151 0.3035 0.055 Uiso 1 calc . .
N1 N 0.29063(11) 0.2097(3) 0.59336(6) 0.0228(3) Uani 1 d . .
N2 N 0.20121(12) 0.3812(3) 0.59712(6) 0.0248(3) Uani 1 d . .
O5 O 0.42367(10) 0.1202(3) 0.52895(5) 0.0290(3) Uani 1 d . .
H5 H 0.439 0.1713 0.4977 0.044 Uiso 1 calc . .
O41 O 0.40316(10) 0.4341(3) 0.44466(5) 0.0297(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.323(2) . ?
C3 C4 1.438(2) . ?
C3 C31 1.502(3) . ?
C4 C5 1.400(3) . ?
C4 C41 1.448(2) . ?
C5 O5 1.322(2) . ?
C5 N1 1.353(2) . ?
C11 C16 1.393(3) . ?
C11 C12 1.397(2) . ?
C11 N1 1.428(2) . ?
C12 C13 1.392(3) . ?
C13 C14 1.392(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.387(3) . ?
C41 O41 1.262(2) . ?
C41 C42 1.486(3) . ?
C42 C43 1.395(2) . ?
C42 C47 1.397(3) . ?
C47 C46 1.385(3) . ?
C46 C45 1.403(2) . ?
C45 C44 1.390(3) . ?
C45 C48 1.514(3) . ?
C44 C43 1.390(3) . ?
N1 N2 1.404(2) . ?

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
N2 C3 C4 111.26(16) . . ?
N2 C3 C31 118.37(15) . . ?
C4 C3 C31 130.18(16) . . ?
C5 C4 C3 103.84(15) . . ?
C5 C4 C41 118.56(16) . . ?
C3 C4 C41 137.44(17) . . ?
O5 C5 N1 123.74(16) . . ?
O5 C5 C4 127.46(16) . . ?
N1 C5 C4 108.80(15) . . ?
C16 C11 C12 120.02(17) . . ?
C16 C11 N1 121.21(15) . . ?
C12 C11 N1 118.76(16) . . ?
C13 C12 C11 119.33(18) . . ?
C12 C13 C14 120.87(18) . . ?
C15 C14 C13 119.16(18) . . ?
C16 C15 C14 120.70(19) . . ?
C15 C16 C11 119.91(17) . . ?
O41 C41 C4 118.57(16) . . ?
O41 C41 C42 118.67(15) . . ?
C4 C41 C42 122.75(15) . . ?
C43 C42 C47 118.83(17) . . ?
C43 C42 C41 121.53(16) . . ?
C47 C42 C41 119.56(15) . . ?
C46 C47 C42 120.25(16) . . ?
C47 C46 C45 121.10(17) . . ?
C44 C45 C46 118.29(17) . . ?
C44 C45 C48 121.06(16) . . ?
C46 C45 C48 120.65(17) . . ?
C43 C44 C45 120.87(16) . . ?
C44 C43 C42 120.62(17) . . ?
C5 N1 N2 109.77(14) . . ?
C5 N1 C11 129.77(15) . . ?
N2 N1 C11 120.41(14) . . ?
C3 N2 N1 106.31(14) . . ?

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
N2 C3 C4 C5 -1.06(19) . . . . ?
C31 C3 C4 C5 173.73(17) . . . . ?
N2 C3 C4 C41 -176.12(19) . . . . ?
C31 C3 C4 C41 -1.3(3) . . . . ?
C3 C4 C5 O5 -177.81(17) . . . . ?
C41 C4 C5 O5 -1.6(3) . . . . ?
C3 C4 C5 N1 1.49(19) . . . . ?
C41 C4 C5 N1 177.69(15) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
N1 C11 C12 C13 179.03(16) . . . . ?
C11 C12 C13 C14 1.4(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
N1 C11 C16 C15 179.94(15) . . . . ?
C5 C4 C41 O41 -7.3(2) . . . . ?
C3 C4 C41 O41 167.27(19) . . . . ?
C5 C4 C41 C42 171.85(16) . . . . ?
C3 C4 C41 C42 -13.6(3) . . . . ?
O41 C41 C42 C43 137.83(18) . . . . ?
C4 C41 C42 C43 -41.3(3) . . . . ?
O41 C41 C42 C47 -38.9(2) . . . . ?
C4 C41 C42 C47 141.94(18) . . . . ?
C43 C42 C47 C46 1.9(3) . . . . ?
C41 C42 C47 C46 178.76(17) . . . . ?
C42 C47 C46 C45 -1.8(3) . . . . ?
C47 C46 C45 C44 0.4(3) . . . . ?
C47 C46 C45 C48 -179.18(18) . . . . ?
C46 C45 C44 C43 0.9(3) . . . . ?
C48 C45 C44 C43 -179.49(17) . . . . ?
C45 C44 C43 C42 -0.8(3) . . . . ?
C47 C42 C43 C44 -0.6(3) . . . . ?
C41 C42 C43 C44 -177.37(17) . . . . ?
O5 C5 N1 N2 177.89(15) . . . . ?
C4 C5 N1 N2 -1.44(19) . . . . ?
O5 C5 N1 C11 0.5(3) . . . . ?
C4 C5 N1 C11 -178.80(16) . . . . ?
C16 C11 N1 C5 -12.5(3) . . . . ?
C12 C11 N1 C5 167.80(17) . . . . ?
C16 C11 N1 N2 170.34(15) . . . . ?
C12 C11 N1 N2 -9.3(2) . . . . ?
C4 C3 N2 N1 0.23(19) . . . . ?
C31 C3 N2 N1 -175.25(14) . . . . ?
C5 N1 N2 C3 0.75(18) . . . . ?
C11 N1 N2 C3 178.39(14) . . . . ?




####################################################################### 
# 
# 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_exp_311_rt
_database_code_depnum_ccdc_archive 'CCDC 1406729'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-05-25T16:37:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_cell_length_a                   11.8744(7)
_cell_length_b                   5.3140(5)
_cell_length_c                   23.4934(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.072(5)
_cell_angle_gamma                90
_cell_volume                     1471.17(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2230
_cell_measurement_theta_min      4.0510
_cell_measurement_theta_max      25.4550

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

_exptl_crystal_density_diffrn    1.32
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.76760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_number            7687
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.458
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_point_group_measured_fraction_ful 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.851
_reflns_number_total             3086
_reflns_number_gt                1931
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0568P)²+0.1817P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   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
C3 C 0.19561(16) 0.5172(5) 0.54982(9) 0.0499(6) Uani 1 d . .
C4 C 0.27717(16) 0.4406(5) 0.51348(9) 0.0499(6) Uani 1 d . .
C5 C 0.33717(16) 0.2496(5) 0.54410(9) 0.0514(6) Uani 1 d . .
C11 C 0.32491(17) 0.0425(5) 0.63904(9) 0.0529(6) Uani 1 d . .
C12 C 0.27852(19) 0.0708(6) 0.68973(10) 0.0650(7) Uani 1 d . .
H12 H 0.2276 0.2006 0.6939 0.078 Uiso 1 calc . .
C13 C 0.3086(2) -0.0964(6) 0.73442(11) 0.0780(8) Uani 1 d . .
H13 H 0.2765 -0.0797 0.7684 0.094 Uiso 1 calc . .
C14 C 0.3852(2) -0.2862(6) 0.72911(11) 0.0751(8) Uani 1 d . .
H14 H 0.4058 -0.3959 0.7595 0.09 Uiso 1 calc . .
C15 C 0.4310(2) -0.3123(6) 0.67858(11) 0.0679(7) Uani 1 d . .
H15 H 0.483 -0.4402 0.6748 0.082 Uiso 1 calc . .
C16 C 0.40072(18) -0.1510(5) 0.63357(10) 0.0591(6) Uani 1 d . .
H16 H 0.4313 -0.1721 0.5993 0.071 Uiso 1 calc . .
C31 C 0.11301(18) 0.7309(5) 0.54375(10) 0.0602(6) Uani 1 d . .
H31A H 0.0479 0.6845 0.5175 0.09 Uiso 1 calc . .
H31B H 0.1484 0.8761 0.5294 0.09 Uiso 1 calc . .
H31C H 0.0897 0.7691 0.5805 0.09 Uiso 1 calc . .
C41 C 0.31122(17) 0.5183(5) 0.45984(9) 0.0532(6) Uani 1 d . .
C42 C 0.24538(17) 0.6938(5) 0.42021(8) 0.0518(6) Uani 1 d . .
C47 C 0.30045(18) 0.8725(5) 0.39116(9) 0.0598(7) Uani 1 d . .
H47 H 0.3792 0.8834 0.3972 0.072 Uiso 1 calc . .
C46 C 0.2396(2) 1.0346(6) 0.35336(10) 0.0652(7) Uani 1 d . .
H46 H 0.2779 1.1574 0.3351 0.078 Uiso 1 calc . .
C45 C 0.1227(2) 1.0185(5) 0.34203(9) 0.0586(6) Uani 1 d . .
C44 C 0.06850(18) 0.8363(5) 0.37017(9) 0.0608(7) Uani 1 d . .
H44 H -0.01 0.821 0.3629 0.073 Uiso 1 calc . .
C43 C 0.12850(18) 0.6759(5) 0.40894(9) 0.0605(7) Uani 1 d . .
H43 H 0.0901 0.5547 0.4277 0.073 Uiso 1 calc . .
C48 C 0.0572(2) 1.1932(6) 0.29977(11) 0.0833(9) Uani 1 d . .
H48A H 0.0698 1.1474 0.2615 0.125 Uiso 1 calc . .
H48B H 0.0822 1.363 0.3074 0.125 Uiso 1 calc . .
H48C H -0.0223 1.1807 0.3034 0.125 Uiso 1 calc . .
N1 N 0.29243(14) 0.2122(4) 0.59328(7) 0.0510(5) Uani 1 d . .
N2 N 0.20438(14) 0.3830(4) 0.59695(7) 0.0551(5) Uani 1 d . .
O5 O 0.42363(12) 0.1211(4) 0.52975(6) 0.0649(5) Uani 1 d . .
H5 H 0.4391 0.1702 0.4985 0.097 Uiso 1 calc . .
O41 O 0.40227(12) 0.4283(4) 0.44516(6) 0.0669(5) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.310(3) . ?
C3 C4 1.427(3) . ?
C3 C31 1.496(3) . ?
C4 C5 1.389(3) . ?
C4 C41 1.431(3) . ?
C5 O5 1.311(3) . ?
C5 N1 1.345(3) . ?
C11 C12 1.380(3) . ?
C11 C16 1.383(3) . ?
C11 N1 1.420(3) . ?
C12 C13 1.388(4) . ?
C13 C14 1.374(4) . ?
C14 C15 1.372(4) . ?
C15 C16 1.374(3) . ?
C41 O41 1.268(3) . ?
C41 C42 1.473(3) . ?
C42 C47 1.380(3) . ?
C42 C43 1.384(3) . ?
C47 C46 1.376(3) . ?
C46 C45 1.384(3) . ?
C45 C44 1.376(3) . ?
C45 C48 1.504(4) . ?
C44 C43 1.380(3) . ?
N1 N2 1.395(3) . ?

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
N2 C3 C4 111.2(2) . . ?
N2 C3 C31 118.48(18) . . ?
C4 C3 C31 130.2(2) . . ?
C5 C4 C3 103.97(19) . . ?
C5 C4 C41 119.0(2) . . ?
C3 C4 C41 136.9(2) . . ?
O5 C5 N1 123.3(2) . . ?
O5 C5 C4 127.98(19) . . ?
N1 C5 C4 108.74(19) . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 N1 118.9(2) . . ?
C16 C11 N1 121.4(2) . . ?
C11 C12 C13 119.3(3) . . ?
C14 C13 C12 120.8(2) . . ?
C15 C14 C13 119.3(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C11 120.2(2) . . ?
O41 C41 C4 118.3(2) . . ?
O41 C41 C42 118.09(19) . . ?
C4 C41 C42 123.6(2) . . ?
C47 C42 C43 118.5(2) . . ?
C47 C42 C41 120.09(19) . . ?
C43 C42 C41 121.3(2) . . ?
C46 C47 C42 120.5(2) . . ?
C47 C46 C45 121.3(2) . . ?
C44 C45 C46 117.9(2) . . ?
C44 C45 C48 121.1(2) . . ?
C46 C45 C48 120.9(2) . . ?
C45 C44 C43 121.2(2) . . ?
C44 C43 C42 120.5(2) . . ?
C5 N1 N2 109.59(18) . . ?
C5 N1 C11 130.2(2) . . ?
N2 N1 C11 120.13(17) . . ?
C3 N2 N1 106.50(16) . . ?

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
N2 C3 C4 C5 -1.0(2) . . . . ?
C31 C3 C4 C5 173.6(2) . . . . ?
N2 C3 C4 C41 -177.0(2) . . . . ?
C31 C3 C4 C41 -2.3(4) . . . . ?
C3 C4 C5 O5 -178.1(2) . . . . ?
C41 C4 C5 O5 -1.3(4) . . . . ?
C3 C4 C5 N1 1.7(2) . . . . ?
C41 C4 C5 N1 178.56(19) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?
N1 C11 C12 C13 179.1(2) . . . . ?
C11 C12 C13 C14 1.1(4) . . . . ?
C12 C13 C14 C15 -1.0(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
N1 C11 C16 C15 179.8(2) . . . . ?
C5 C4 C41 O41 -7.3(3) . . . . ?
C3 C4 C41 O41 168.1(2) . . . . ?
C5 C4 C41 C42 171.6(2) . . . . ?
C3 C4 C41 C42 -13.0(4) . . . . ?
O41 C41 C42 C47 -40.2(3) . . . . ?
C4 C41 C42 C47 140.9(2) . . . . ?
O41 C41 C42 C43 136.4(2) . . . . ?
C4 C41 C42 C43 -42.5(3) . . . . ?
C43 C42 C47 C46 2.2(4) . . . . ?
C41 C42 C47 C46 179.0(2) . . . . ?
C42 C47 C46 C45 -2.0(4) . . . . ?
C47 C46 C45 C44 0.6(4) . . . . ?
C47 C46 C45 C48 -178.8(2) . . . . ?
C46 C45 C44 C43 0.6(4) . . . . ?
C48 C45 C44 C43 180.0(2) . . . . ?
C45 C44 C43 C42 -0.4(4) . . . . ?
C47 C42 C43 C44 -1.0(3) . . . . ?
C41 C42 C43 C44 -177.7(2) . . . . ?
O5 C5 N1 N2 177.99(19) . . . . ?
C4 C5 N1 N2 -1.9(2) . . . . ?
O5 C5 N1 C11 1.1(4) . . . . ?
C4 C5 N1 C11 -178.7(2) . . . . ?
C12 C11 N1 C5 168.3(2) . . . . ?
C16 C11 N1 C5 -12.4(3) . . . . ?
C12 C11 N1 N2 -8.3(3) . . . . ?
C16 C11 N1 N2 171.03(19) . . . . ?
C4 C3 N2 N1 0.0(2) . . . . ?
C31 C3 N2 N1 -175.42(18) . . . . ?
C5 N1 N2 C3 1.2(2) . . . . ?
C11 N1 N2 C3 178.43(18) . . . . ?




####################################################################### 
# 
# 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_exp_284_5
_database_code_depnum_ccdc_archive 'CCDC 1406730'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-19T16:28:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
_cell_length_a                   7.4723(5)
_cell_length_b                   17.3131(8)
_cell_length_c                   11.3273(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1465.40(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    844
_cell_measurement_theta_min      3.9550
_cell_measurement_theta_max      25.2440
#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_min  0.14616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_number            5628
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.472
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_ful 0.887
_diffrn_reflns_point_group_measured_fraction_max 0.881
_reflns_number_total             2648
_reflns_number_gt                1919
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.1109P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2648
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2003
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.7(10)
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   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
C3 C 0.5882(7) 0.7627(3) 0.6852(5) 0.0289(13) Uani 1 d . .
C4 C 0.6336(8) 0.7439(3) 0.5651(5) 0.0287(13) Uani 1 d . .
C5 C 0.6546(7) 0.8161(4) 0.5126(5) 0.0323(13) Uani 1 d . .
C11 C 0.6243(7) 0.9528(3) 0.5798(5) 0.0282(13) Uani 1 d . .
C12 C 0.6744(7) 0.9990(3) 0.6773(5) 0.0319(13) Uani 1 d . .
H12 H 0.7144 0.976 0.7487 0.038 Uiso 1 calc . .
C13 C 0.6638(8) 1.0778(3) 0.6666(6) 0.0379(14) Uani 1 d . .
H13 H 0.6957 1.1095 0.7318 0.046 Uiso 1 calc . .
C14 C 0.6071(8) 1.1121(4) 0.5615(6) 0.0416(16) Uani 1 d . .
H14 H 0.6004 1.1667 0.555 0.05 Uiso 1 calc . .
C15 C 0.5602(7) 1.0652(3) 0.4661(5) 0.0346(13) Uani 1 d . .
H15 H 0.5235 1.0883 0.394 0.041 Uiso 1 calc . .
C16 C 0.5663(6) 0.9866(4) 0.4753(5) 0.0322(13) Uani 1 d . .
H16 H 0.5311 0.9552 0.4106 0.039 Uiso 1 calc . .
C31 C 0.5419(9) 0.7122(4) 0.7886(5) 0.0392(15) Uani 1 d . .
H31A H 0.4759 0.7425 0.8473 0.059 Uiso 1 calc . .
H31B H 0.6521 0.6921 0.8241 0.059 Uiso 1 calc . .
H31C H 0.4675 0.669 0.7617 0.059 Uiso 1 calc . .
C41 C 0.6481(7) 0.6772(3) 0.4936(5) 0.0330(14) Uani 1 d . .
C42 C 0.6326(7) 0.5949(3) 0.5322(6) 0.0328(14) Uani 1 d . .
C43 C 0.6970(7) 0.5689(3) 0.6400(6) 0.0331(13) Uani 1 d . .
H43 H 0.7453 0.6044 0.6954 0.04 Uiso 1 calc . .
C44 C 0.6903(7) 0.4908(3) 0.6664(5) 0.0347(14) Uani 1 d . .
H44 H 0.7361 0.4731 0.7398 0.042 Uiso 1 calc . .
C45 C 0.6174(7) 0.4377(3) 0.5869(6) 0.0334(14) Uani 1 d . .
C46 C 0.5512(7) 0.4651(4) 0.4807(6) 0.0368(14) Uani 1 d . .
H46 H 0.4997 0.4299 0.4261 0.044 Uiso 1 calc . .
C47 C 0.5584(7) 0.5424(3) 0.4528(5) 0.0329(13) Uani 1 d . .
H47 H 0.5128 0.56 0.3793 0.039 Uiso 1 calc . .
C48 C 0.6137(9) 0.3528(4) 0.6160(7) 0.0464(18) Uani 1 d . .
H48A H 0.7235 0.3283 0.587 0.07 Uiso 1 calc . .
H48B H 0.5097 0.3287 0.5783 0.07 Uiso 1 calc . .
H48C H 0.6056 0.3461 0.7018 0.07 Uiso 1 calc . .
N1 N 0.6252(6) 0.8717(3) 0.5921(4) 0.0310(11) Uani 1 d . .
N2 N 0.5838(6) 0.8380(3) 0.7017(4) 0.0325(11) Uani 1 d . .
O5 O 0.6937(6) 0.8307(2) 0.4008(4) 0.0439(12) Uani 1 d . .
H5 H 0.698 0.7891 0.3628 0.066 Uiso 1 calc . .
O41 O 0.6773(7) 0.6875(3) 0.3824(4) 0.0511(13) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.316(7) . ?
C3 C4 1.440(8) . ?
C3 C31 1.502(8) . ?
C4 C5 1.393(8) . ?
C4 C41 1.413(8) . ?
C5 O5 1.325(7) . ?
C5 N1 1.336(8) . ?
C11 C16 1.390(8) . ?
C11 C12 1.415(8) . ?
C11 N1 1.411(7) . ?
C12 C13 1.372(9) . ?
C12 H12 0.95 . ?
C13 C14 1.396(9) . ?
C13 H13 0.95 . ?
C14 C15 1.396(9) . ?
C14 H14 0.95 . ?
C15 C16 1.366(8) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C41 O41 1.290(7) . ?
C41 C42 1.495(8) . ?
C42 C43 1.388(9) . ?
C42 C47 1.393(8) . ?
C43 C44 1.385(8) . ?
C43 H43 0.95 . ?
C44 C45 1.397(8) . ?
C44 H44 0.95 . ?
C45 C46 1.384(9) . ?
C45 C48 1.508(9) . ?
C46 C47 1.376(8) . ?
C46 H46 0.95 . ?
C47 H47 0.95 . ?
C48 H48A 0.98 . ?
C48 H48B 0.98 . ?
C48 H48C 0.98 . ?
N1 N2 1.406(7) . ?
O5 H5 0.84 . ?

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
N2 C3 C4 111.4(5) . . ?
N2 C3 C31 117.4(5) . . ?
C4 C3 C31 131.2(5) . . ?
C5 C4 C3 103.1(5) . . ?
C5 C4 C41 118.6(5) . . ?
C3 C4 C41 138.1(5) . . ?
O5 C5 N1 122.9(5) . . ?
O5 C5 C4 127.2(5) . . ?
N1 C5 C4 109.9(5) . . ?
C16 C11 C12 120.6(5) . . ?
C16 C11 N1 120.3(5) . . ?
C12 C11 N1 119.0(5) . . ?
C13 C12 C11 118.6(6) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.3(6) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.8(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.7(6) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 117.4(5) . . ?
O41 C41 C42 115.4(5) . . ?
C4 C41 C42 127.2(5) . . ?
C43 C42 C47 119.6(6) . . ?
C43 C42 C41 122.6(6) . . ?
C47 C42 C41 117.7(6) . . ?
C42 C43 C44 119.6(6) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C43 C44 C45 121.1(6) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C46 C45 C44 118.3(6) . . ?
C46 C45 C48 121.2(5) . . ?
C44 C45 C48 120.5(6) . . ?
C47 C46 C45 121.2(6) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C42 120.1(6) . . ?
C46 C47 H47 119.9 . . ?
C42 C47 H47 119.9 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C5 N1 N2 109.4(5) . . ?
C5 N1 C11 130.6(5) . . ?
N2 N1 C11 119.9(4) . . ?
C3 N2 N1 106.3(5) . . ?
C5 O5 H5 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
N2 C3 C4 C5 -0.2(6) . . . . ?
C31 C3 C4 C5 177.7(6) . . . . ?
N2 C3 C4 C41 -175.1(7) . . . . ?
C31 C3 C4 C41 2.8(11) . . . . ?
C3 C4 C5 O5 -178.6(6) . . . . ?
C41 C4 C5 O5 -2.5(9) . . . . ?
C3 C4 C5 N1 0.0(6) . . . . ?
C41 C4 C5 N1 176.1(5) . . . . ?
C16 C11 C12 C13 0.2(8) . . . . ?
N1 C11 C12 C13 -176.5(5) . . . . ?
C11 C12 C13 C14 -0.8(9) . . . . ?
C12 C13 C14 C15 0.1(10) . . . . ?
C13 C14 C15 C16 1.1(9) . . . . ?
C12 C11 C16 C15 1.0(8) . . . . ?
N1 C11 C16 C15 177.7(5) . . . . ?
C14 C15 C16 C11 -1.7(8) . . . . ?
C5 C4 C41 O41 -1.2(8) . . . . ?
C3 C4 C41 O41 173.2(7) . . . . ?
C5 C4 C41 C42 179.2(5) . . . . ?
C3 C4 C41 C42 -6.5(11) . . . . ?
O41 C41 C42 C43 143.8(6) . . . . ?
C4 C41 C42 C43 -36.6(9) . . . . ?
O41 C41 C42 C47 -32.8(8) . . . . ?
C4 C41 C42 C47 146.8(6) . . . . ?
C47 C42 C43 C44 1.4(8) . . . . ?
C41 C42 C43 C44 -175.1(5) . . . . ?
C42 C43 C44 C45 -0.9(8) . . . . ?
C43 C44 C45 C46 -0.2(8) . . . . ?
C43 C44 C45 C48 179.1(6) . . . . ?
C44 C45 C46 C47 0.8(8) . . . . ?
C48 C45 C46 C47 -178.4(6) . . . . ?
C45 C46 C47 C42 -0.3(8) . . . . ?
C43 C42 C47 C46 -0.8(8) . . . . ?
C41 C42 C47 C46 175.9(5) . . . . ?
O5 C5 N1 N2 178.9(5) . . . . ?
C4 C5 N1 N2 0.3(6) . . . . ?
O5 C5 N1 C11 1.2(9) . . . . ?
C4 C5 N1 C11 -177.4(6) . . . . ?
C16 C11 N1 C5 33.3(9) . . . . ?
C12 C11 N1 C5 -149.9(6) . . . . ?
C16 C11 N1 N2 -144.1(5) . . . . ?
C12 C11 N1 N2 32.6(8) . . . . ?
C4 C3 N2 N1 0.4(6) . . . . ?
C31 C3 N2 N1 -177.8(5) . . . . ?
C5 N1 N2 C3 -0.4(6) . . . . ?
C11 N1 N2 C3 177.6(5) . . . . ?
C3 C4 C41 C42 -6.5(11) . . . . ?
C4 C41 C42 C43 -36.6(9) . . . . ?
C5 N1 C11 C16 33.3(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
C16 H16 O5 0.95 2.48 2.984(7) 113.4 .
O5 H5 O41 0.84 1.78 2.493(6) 141.4 .





####################################################################### 
# 
# 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_exp_188_v02
_database_code_depnum_ccdc_archive 'CCDC 1406731'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-27T11:18:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
_cell_length_a                   7.6060(6)
_cell_length_b                   17.2147(9)
_cell_length_c                   11.3303(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1483.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1744
_cell_measurement_theta_min      4.3050
_cell_measurement_theta_max      25.9180

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.63098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

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

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_number            5359
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.928
_diffrn_reflns_theta_max         26.334
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_ful 0.864
_diffrn_reflns_point_group_measured_fraction_max 0.851
_reflns_number_total             2574
_reflns_number_gt                1852
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.1019P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2574
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1964
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -4.3(10)
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   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
C3 C 0.9155(6) 0.7630(3) 0.2961(5) 0.0526(13) Uani 1 d . .
C4 C 0.8702(7) 0.7447(3) 0.1773(5) 0.0496(12) Uani 1 d . .
C5 C 0.8488(7) 0.8169(3) 0.1239(5) 0.0579(13) Uani 1 d . .
C11 C 0.8772(6) 0.9536(3) 0.1922(5) 0.0499(12) Uani 1 d . .
C12 C 0.8271(6) 0.9982(3) 0.2878(5) 0.0569(13) Uani 1 d . .
H12 H 0.7887 0.9745 0.357 0.068 Uiso 1 calc . .
C13 C 0.8344(8) 1.0771(3) 0.2799(6) 0.0700(16) Uani 1 d . .
H13 H 0.8027 1.1078 0.344 0.084 Uiso 1 calc . .
C14 C 0.8895(8) 1.1112(4) 0.1754(6) 0.0744(18) Uani 1 d . .
H14 H 0.8946 1.165 0.1694 0.089 Uiso 1 calc . .
C15 C 0.9365(7) 1.0661(3) 0.0811(5) 0.0652(14) Uani 1 d . .
H15 H 0.9713 1.0896 0.0109 0.078 Uiso 1 calc . .
C16 C 0.9328(6) 0.9875(3) 0.0890(5) 0.0566(13) Uani 1 d . .
H16 H 0.9674 0.9569 0.0255 0.068 Uiso 1 calc . .
C31 C 0.9590(9) 0.7111(3) 0.3964(5) 0.0699(15) Uani 1 d . .
H31A H 0.8542 0.6855 0.4231 0.105 Uiso 1 calc . .
H31B H 1.0078 0.7412 0.4597 0.105 Uiso 1 calc . .
H31C H 1.0432 0.673 0.3713 0.105 Uiso 1 calc . .
C41 C 0.8560(7) 0.6767(3) 0.1063(6) 0.0637(15) Uani 1 d . .
C42 C 0.8696(7) 0.5962(3) 0.1441(5) 0.0579(14) Uani 1 d . .
C43 C 0.9428(7) 0.5426(3) 0.0669(5) 0.0655(15) Uani 1 d . .
H43 H 0.9882 0.5593 -0.005 0.079 Uiso 1 calc . .
C44 C 0.9486(7) 0.4663(3) 0.0954(6) 0.0660(15) Uani 1 d . .
H44 H 1.0008 0.4317 0.0428 0.079 Uiso 1 calc . .
C45 C 0.8801(7) 0.4379(3) 0.1993(6) 0.0614(14) Uani 1 d . .
C46 C 0.8075(7) 0.4917(3) 0.2766(5) 0.0619(14) Uani 1 d . .
H46 H 0.7612 0.4748 0.3481 0.074 Uiso 1 calc . .
C47 C 0.8029(7) 0.5694(3) 0.2493(5) 0.0615(14) Uani 1 d . .
H47 H 0.7541 0.6044 0.3026 0.074 Uiso 1 calc . .
C48 C 0.8824(9) 0.3540(4) 0.2279(7) 0.086(2) Uani 1 d . .
H48A H 0.9792 0.3296 0.1881 0.129 Uiso 1 calc . .
H48B H 0.7742 0.3306 0.2025 0.129 Uiso 1 calc . .
H48C H 0.8953 0.3473 0.3116 0.129 Uiso 1 calc . .
N1 N 0.8752(6) 0.8718(3) 0.2031(4) 0.0539(11) Uani 1 d . .
N2 N 0.9194(5) 0.8373(3) 0.3130(4) 0.0568(11) Uani 1 d . .
O5 O 0.8109(6) 0.8317(2) 0.0145(4) 0.0848(13) Uani 1 d . .
H5 H 0.8001 0.7908 -0.0218 0.127 Uiso 1 calc . .
O41 O 0.8263(7) 0.6883(3) -0.0047(4) 0.0969(15) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.294(6) . ?
C3 C4 1.425(7) . ?
C3 C31 1.483(7) . ?
C4 C5 1.391(8) . ?
C4 C41 1.424(7) . ?
C5 O5 1.298(6) . ?
C5 N1 1.318(7) . ?
C11 C16 1.373(8) . ?
C11 C12 1.381(8) . ?
C11 N1 1.414(6) . ?
C12 C13 1.362(8) . ?
C12 H12 0.93 . ?
C13 C14 1.387(9) . ?
C13 H13 0.93 . ?
C14 C15 1.368(8) . ?
C14 H14 0.93 . ?
C15 C16 1.358(7) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C41 O41 1.293(7) . ?
C41 C42 1.454(8) . ?
C42 C47 1.374(8) . ?
C42 C43 1.388(8) . ?
C43 C44 1.354(8) . ?
C43 H43 0.93 . ?
C44 C45 1.378(9) . ?
C44 H44 0.93 . ?
C45 C46 1.389(8) . ?
C45 C48 1.480(9) . ?
C46 C47 1.373(8) . ?
C46 H46 0.93 . ?
C47 H47 0.93 . ?
C48 H48A 0.96 . ?
C48 H48B 0.96 . ?
C48 H48C 0.96 . ?
N1 N2 1.420(6) . ?
O5 H5 0.82 . ?

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
N2 C3 C4 111.3(5) . . ?
N2 C3 C31 118.5(5) . . ?
C4 C3 C31 130.2(5) . . ?
C5 C4 C41 118.7(5) . . ?
C5 C4 C3 104.0(4) . . ?
C41 C4 C3 137.1(5) . . ?
O5 C5 N1 122.8(5) . . ?
O5 C5 C4 128.1(5) . . ?
N1 C5 C4 109.1(5) . . ?
C16 C11 C12 121.2(5) . . ?
C16 C11 N1 120.0(5) . . ?
C12 C11 N1 118.8(5) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 119.4(6) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.4(6) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.6(6) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.1(5) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 115.8(5) . . ?
O41 C41 C42 116.5(5) . . ?
C4 C41 C42 127.7(5) . . ?
C47 C42 C43 118.1(5) . . ?
C47 C42 C41 123.3(5) . . ?
C43 C42 C41 118.4(5) . . ?
C44 C43 C42 120.5(6) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 122.4(6) . . ?
C43 C44 H44 118.8 . . ?
C45 C44 H44 118.8 . . ?
C44 C45 C46 116.9(5) . . ?
C44 C45 C48 121.9(5) . . ?
C46 C45 C48 121.2(6) . . ?
C47 C46 C45 121.2(6) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C46 C47 C42 120.9(5) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C5 N1 C11 131.1(5) . . ?
C5 N1 N2 109.4(4) . . ?
C11 N1 N2 119.4(4) . . ?
C3 N2 N1 106.2(4) . . ?
C5 O5 H5 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
N2 C3 C4 C5 0.5(6) . . . . ?
C31 C3 C4 C5 -178.4(6) . . . . ?
N2 C3 C4 C41 175.3(6) . . . . ?
C31 C3 C4 C41 -3.6(10) . . . . ?
C41 C4 C5 O5 2.3(9) . . . . ?
C3 C4 C5 O5 178.2(6) . . . . ?
C41 C4 C5 N1 -177.0(5) . . . . ?
C3 C4 C5 N1 -1.1(5) . . . . ?
C16 C11 C12 C13 -0.5(8) . . . . ?
N1 C11 C12 C13 177.7(5) . . . . ?
C11 C12 C13 C14 0.9(8) . . . . ?
C12 C13 C14 C15 -0.1(9) . . . . ?
C13 C14 C15 C16 -1.1(9) . . . . ?
C14 C15 C16 C11 1.5(8) . . . . ?
C12 C11 C16 C15 -0.7(7) . . . . ?
N1 C11 C16 C15 -178.9(4) . . . . ?
C5 C4 C41 O41 1.1(8) . . . . ?
C3 C4 C41 O41 -173.1(6) . . . . ?
C5 C4 C41 C42 -178.4(5) . . . . ?
C3 C4 C41 C42 7.4(10) . . . . ?
O41 C41 C42 C47 -141.5(6) . . . . ?
C4 C41 C42 C47 38.0(8) . . . . ?
O41 C41 C42 C43 34.0(7) . . . . ?
C4 C41 C42 C43 -146.5(6) . . . . ?
C47 C42 C43 C44 -0.3(8) . . . . ?
C41 C42 C43 C44 -176.1(5) . . . . ?
C42 C43 C44 C45 1.5(9) . . . . ?
C43 C44 C45 C46 -1.6(8) . . . . ?
C43 C44 C45 C48 178.1(6) . . . . ?
C44 C45 C46 C47 0.8(8) . . . . ?
C48 C45 C46 C47 -179.0(5) . . . . ?
C45 C46 C47 C42 0.3(8) . . . . ?
C43 C42 C47 C46 -0.5(8) . . . . ?
C41 C42 C47 C46 175.0(5) . . . . ?
O5 C5 N1 C11 -2.7(9) . . . . ?
C4 C5 N1 C11 176.6(5) . . . . ?
O5 C5 N1 N2 -178.1(5) . . . . ?
C4 C5 N1 N2 1.2(5) . . . . ?
C16 C11 N1 C5 -31.6(8) . . . . ?
C12 C11 N1 C5 150.2(5) . . . . ?
C16 C11 N1 N2 143.4(5) . . . . ?
C12 C11 N1 N2 -34.8(6) . . . . ?
C4 C3 N2 N1 0.2(6) . . . . ?
C31 C3 N2 N1 179.2(4) . . . . ?
C5 N1 N2 C3 -0.9(6) . . . . ?
C11 N1 N2 C3 -176.9(4) . . . . ?
C3 C4 C41 C42 7.4(10) . . . . ?
C4 C41 C42 C43 -146.5(6) . . . . ?
C5 N1 C11 C16 -31.6(8) . . . . ?

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
C16 H16 O5 0.93 2.46 2.959(7) 113.4 .
O5 H5 O41 0.82 1.79 2.481(6) 141.5 .
C16 H16 O5 0.93 2.46 2.959(7) 113.4 .
O5 H5 O41 0.82 1.79 2.481(6) 141.5 .





####################################################################### 
# 
# 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_exp_284
_database_code_depnum_ccdc_archive 'CCDC 1406732'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-19T15:27:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_cell_length_a                   10.9709(4)
_cell_length_b                   11.8263(3)
_cell_length_c                   11.9472(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.334(4)
_cell_angle_gamma                90
_cell_volume                     1453.49(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorles
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_min  0.66414
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_number            8715
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.445
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_ful 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             2669
_reflns_number_gt                2458
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0404P)²+1.2360P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2669
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   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
C3 C 0.36023(16) 0.33000(13) 0.69205(14) 0.0186(3) Uani 1 d . .
C4 C 0.35179(16) 0.31406(14) 0.80433(14) 0.0189(3) Uani 1 d . .
C5 C 0.47017(16) 0.25962(14) 0.87670(14) 0.0185(3) Uani 1 d . .
C11 C 0.67083(15) 0.20478(13) 0.82794(14) 0.0186(3) Uani 1 d . .
C12 C 0.70558(16) 0.15863(14) 0.73622(15) 0.0211(4) Uani 1 d . .
H12 H 0.6434 0.153 0.6579 0.025 Uiso 1 calc . .
C13 C 0.83149(17) 0.12098(15) 0.76011(16) 0.0253(4) Uani 1 d . .
H13 H 0.8564 0.0914 0.6973 0.03 Uiso 1 calc . .
C14 C 0.92131(17) 0.12615(16) 0.87477(17) 0.0281(4) Uani 1 d . .
H14 H 1.0074 0.0994 0.8908 0.034 Uiso 1 calc . .
C15 C 0.88556(17) 0.17047(16) 0.96612(16) 0.0273(4) Uani 1 d . .
H15 H 0.9471 0.1731 1.045 0.033 Uiso 1 calc . .
C16 C 0.76081(16) 0.21102(15) 0.94335(15) 0.0226(4) Uani 1 d . .
H16 H 0.737 0.2428 1.0058 0.027 Uiso 1 calc . .
C31 C 0.26942(17) 0.38447(15) 0.58272(15) 0.0250(4) Uani 1 d . .
H31A H 0.2594 0.4646 0.5988 0.037 Uiso 1 calc . .
H31B H 0.1846 0.347 0.5595 0.037 Uiso 1 calc . .
H31C H 0.3043 0.3778 0.5178 0.037 Uiso 1 calc . .
C41 C 0.23392(16) 0.34186(14) 0.83111(14) 0.0210(4) Uani 1 d . .
C42 C 0.24341(16) 0.38427(13) 0.95126(15) 0.0199(4) Uani 1 d . .
C47 C 0.13264(17) 0.38283(15) 0.98298(16) 0.0260(4) Uani 1 d . .
H47 H 0.0535 0.3535 0.9288 0.031 Uiso 1 calc . .
C46 C 0.13716(19) 0.42369(16) 1.09255(17) 0.0304(4) Uani 1 d . .
H46 H 0.0614 0.42 1.1137 0.036 Uiso 1 calc . .
C45 C 0.2505(2) 0.47029(15) 1.17274(16) 0.0277(4) Uani 1 d . .
C44 C 0.36010(18) 0.47330(15) 1.13986(15) 0.0256(4) Uani 1 d . .
H44 H 0.4382 0.5055 1.1927 0.031 Uiso 1 calc . .
C43 C 0.35726(16) 0.43007(14) 1.03124(15) 0.0213(4) Uani 1 d . .
H43 H 0.4338 0.4317 1.0111 0.026 Uiso 1 calc . .
C48 C 0.2528(2) 0.51625(19) 1.29096(19) 0.0431(5) Uani 1 d . .
H48A H 0.342 0.5142 1.3482 0.065 Uiso 1 calc . .
H48B H 0.1966 0.47 1.3209 0.065 Uiso 1 calc . .
H48C H 0.2213 0.5945 1.2807 0.065 Uiso 1 calc . .
N1 N 0.54289(13) 0.24744(12) 0.80267(11) 0.0187(3) Uani 1 d . .
N2 N 0.47460(13) 0.29309(12) 0.69265(11) 0.0186(3) Uani 1 d . .
H2 H 0.5025 0.2971 0.6321 0.022 Uiso 1 calc . .
O41 O 0.12705(12) 0.33391(12) 0.75242(11) 0.0327(3) Uani 1 d . .
O5 O 0.50962(11) 0.22366(11) 0.98151(10) 0.0243(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.326(2) . ?
C3 C4 1.389(2) . ?
C3 C31 1.486(2) . ?
C4 C5 1.438(2) . ?
C4 C41 1.473(2) . ?
C5 O5 1.2488(19) . ?
C5 N1 1.389(2) . ?
C11 C12 1.391(2) . ?
C11 C16 1.391(2) . ?
C11 N1 1.422(2) . ?
C12 C13 1.383(2) . ?
C12 H12 0.95 . ?
C13 C14 1.383(3) . ?
C13 H13 0.95 . ?
C14 C15 1.385(3) . ?
C14 H14 0.95 . ?
C15 C16 1.385(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C41 O41 1.225(2) . ?
C41 C42 1.490(2) . ?
C42 C47 1.393(2) . ?
C42 C43 1.392(2) . ?
C47 C46 1.380(3) . ?
C47 H47 0.95 . ?
C46 C45 1.393(3) . ?
C46 H46 0.95 . ?
C45 C44 1.389(3) . ?
C45 C48 1.505(3) . ?
C44 C43 1.385(2) . ?
C44 H44 0.95 . ?
C43 H43 0.95 . ?
C48 H48A 0.98 . ?
C48 H48B 0.98 . ?
C48 H48C 0.98 . ?
N1 N2 1.3770(18) . ?
N2 H2 0.88 . ?

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
N2 C3 C4 109.30(14) . . ?
N2 C3 C31 119.44(14) . . ?
C4 C3 C31 131.15(15) . . ?
C3 C4 C5 106.98(14) . . ?
C3 C4 C41 122.52(15) . . ?
C5 C4 C41 130.30(15) . . ?
O5 C5 N1 121.84(15) . . ?
O5 C5 C4 132.94(15) . . ?
N1 C5 C4 105.19(13) . . ?
C12 C11 C16 120.49(15) . . ?
C12 C11 N1 119.51(14) . . ?
C16 C11 N1 119.99(14) . . ?
C13 C12 C11 119.42(15) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.45(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 119.86(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.49(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.26(16) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 119.62(15) . . ?
O41 C41 C42 119.54(15) . . ?
C4 C41 C42 120.78(14) . . ?
C47 C42 C43 118.53(16) . . ?
C47 C42 C41 118.85(15) . . ?
C43 C42 C41 122.56(15) . . ?
C46 C47 C42 120.43(17) . . ?
C46 C47 H47 119.8 . . ?
C42 C47 H47 119.8 . . ?
C47 C46 C45 121.35(17) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C44 C45 C46 117.99(16) . . ?
C44 C45 C48 121.47(18) . . ?
C46 C45 C48 120.54(18) . . ?
C43 C44 C45 121.04(17) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C43 C42 120.64(16) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N2 N1 C5 108.95(13) . . ?
N2 N1 C11 120.75(13) . . ?
C5 N1 C11 130.14(13) . . ?
C3 N2 N1 109.52(13) . . ?
C3 N2 H2 125.2 . . ?
N1 N2 H2 125.2 . . ?

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
N2 C3 C4 C5 -1.93(18) . . . . ?
C31 C3 C4 C5 -178.03(17) . . . . ?
N2 C3 C4 C41 -177.18(14) . . . . ?
C31 C3 C4 C41 6.7(3) . . . . ?
C3 C4 C5 O5 -177.21(18) . . . . ?
C41 C4 C5 O5 -2.5(3) . . . . ?
C3 C4 C5 N1 0.58(18) . . . . ?
C41 C4 C5 N1 175.32(16) . . . . ?
C16 C11 C12 C13 -1.4(2) . . . . ?
N1 C11 C12 C13 177.63(15) . . . . ?
C11 C12 C13 C14 1.8(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C11 1.2(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
N1 C11 C16 C15 -179.13(15) . . . . ?
C3 C4 C41 O41 30.9(2) . . . . ?
C5 C4 C41 O41 -143.17(18) . . . . ?
C3 C4 C41 C42 -146.47(16) . . . . ?
C5 C4 C41 C42 39.5(3) . . . . ?
O41 C41 C42 C47 18.5(2) . . . . ?
C4 C41 C42 C47 -164.17(16) . . . . ?
O41 C41 C42 C43 -158.55(17) . . . . ?
C4 C41 C42 C43 18.8(2) . . . . ?
C43 C42 C47 C46 -1.5(3) . . . . ?
C41 C42 C47 C46 -178.62(16) . . . . ?
C42 C47 C46 C45 1.9(3) . . . . ?
C47 C46 C45 C44 -0.8(3) . . . . ?
C47 C46 C45 C48 178.93(18) . . . . ?
C46 C45 C44 C43 -0.8(3) . . . . ?
C48 C45 C44 C43 179.54(17) . . . . ?
C45 C44 C43 C42 1.2(3) . . . . ?
C47 C42 C43 C44 -0.1(2) . . . . ?
C41 C42 C43 C44 176.99(15) . . . . ?
O5 C5 N1 N2 179.02(14) . . . . ?
C4 C5 N1 N2 0.93(17) . . . . ?
O5 C5 N1 C11 -5.6(3) . . . . ?
C4 C5 N1 C11 176.27(15) . . . . ?
C12 C11 N1 N2 -30.7(2) . . . . ?
C16 C11 N1 N2 148.27(15) . . . . ?
C12 C11 N1 C5 154.40(17) . . . . ?
C16 C11 N1 C5 -26.6(3) . . . . ?
C4 C3 N2 N1 2.56(18) . . . . ?
C31 C3 N2 N1 179.19(14) . . . . ?
C5 N1 N2 C3 -2.19(18) . . . . ?
C11 N1 N2 C3 -178.05(14) . . . . ?
C3 C4 C41 C42 -146.47(16) . . . . ?
C4 C41 C42 C43 18.8(2) . . . . ?
C5 N1 C11 C16 -26.6(3) . . . . ?

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
C12 H12 O5 0.95 2.56 3.358(2) 141.3 4_565
C16 H16 O5 0.95 2.42 2.949(2) 115 .
C31 H31B O41 0.98 2.6 3.018(2) 106 .
N2 H2 O5 0.88 1.84 2.6878(17) 160 4_565







####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1406733'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-27T16:49:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
_cell_length_a                   10.966(5)
_cell_length_b                   12.084(5)
_cell_length_c                   11.968(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.14(4)
_cell_angle_gamma                90
_cell_volume                     1488.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    22
_cell_measurement_theta_min      20.15
_cell_measurement_theta_max      20.95
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             616
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_orient_matrix_type       
;
  x-axis points to radiation source
  the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_ub_11      0.051568
_diffrn_orient_matrix_ub_12      0.070113
_diffrn_orient_matrix_ub_13      0.014219
_diffrn_orient_matrix_ub_21      -0.081864
_diffrn_orient_matrix_ub_22      0.043407
_diffrn_orient_matrix_ub_23      -0.035838
_diffrn_orient_matrix_ub_31      -0.008603
_diffrn_orient_matrix_ub_32      0.006975
_diffrn_orient_matrix_ub_33      0.080213
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_standards_number         3
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 3 -5
3 2 -4
0 2 -4

_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_number            5953
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.978
_diffrn_reflns_theta_max         25.971
_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_ful 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_number_total             2910
_reflns_number_gt                2145
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0693P)²+0.2343P] 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       0.020(3)
_refine_ls_number_reflns         2910
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
#                   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
C3 C 0.35738(17) 0.33016(15) 0.19217(14) 0.0395(4) Uani 1 d . .
C4 C 0.34848(17) 0.31537(15) 0.30406(14) 0.0403(4) Uani 1 d . .
C5 C 0.46548(17) 0.26162(15) 0.37603(14) 0.0390(4) Uani 1 d . .
C11 C 0.66613(16) 0.20605(14) 0.32811(14) 0.0384(4) Uani 1 d . .
C12 C 0.70229(18) 0.16114(16) 0.23735(15) 0.0463(5) Uani 1 d . .
H12 H 0.6422 0.156 0.1606 0.056 Uiso 1 calc . .
C13 C 0.82722(19) 0.12444(18) 0.26157(18) 0.0547(5) Uani 1 d . .
H13 H 0.8521 0.0964 0.2003 0.066 Uiso 1 calc . .
C14 C 0.9160(2) 0.1286(2) 0.37501(19) 0.0607(6) Uani 1 d . .
H14 H 1.0001 0.1029 0.3907 0.073 Uiso 1 calc . .
C15 C 0.87949(19) 0.1712(2) 0.46524(18) 0.0599(6) Uani 1 d . .
H15 H 0.9392 0.1733 0.5424 0.072 Uiso 1 calc . .
C16 C 0.75557(18) 0.21057(17) 0.44262(15) 0.0496(5) Uani 1 d . .
H16 H 0.732 0.2401 0.504 0.06 Uiso 1 calc . .
C31 C 0.2674(2) 0.38368(18) 0.08342(15) 0.0549(5) Uani 1 d . .
H31A H 0.261 0.4612 0.0981 0.082 Uiso 1 calc . .
H31B H 0.1831 0.3502 0.0627 0.082 Uiso 1 calc . .
H31C H 0.2998 0.3742 0.0191 0.082 Uiso 1 calc . .
C41 C 0.23097(18) 0.34387(16) 0.33147(15) 0.0451(5) Uani 1 d . .
C42 C 0.24132(17) 0.38559(15) 0.45135(15) 0.0413(4) Uani 1 d . .
C47 C 0.1317(2) 0.38218(18) 0.48418(18) 0.0551(5) Uani 1 d . .
H47 H 0.0546 0.3526 0.4325 0.066 Uiso 1 calc . .
C46 C 0.1374(2) 0.4229(2) 0.5937(2) 0.0650(6) Uani 1 d . .
H46 H 0.0638 0.4189 0.6154 0.078 Uiso 1 calc . .
C45 C 0.2494(2) 0.46929(17) 0.67194(18) 0.0585(6) Uani 1 d . .
C44 C 0.3570(2) 0.47352(16) 0.63767(17) 0.0549(5) Uani 1 d . .
H44 H 0.4332 0.5053 0.6884 0.066 Uiso 1 calc . .
C43 C 0.35387(18) 0.43146(16) 0.52935(15) 0.0461(5) Uani 1 d . .
H43 H 0.4282 0.4341 0.5088 0.055 Uiso 1 calc . .
C48 C 0.2521(3) 0.5145(3) 0.7903(2) 0.0934(9) Uani 1 d . .
H48A H 0.3398 0.514 0.8453 0.14 Uiso 1 calc . .
H48B H 0.1987 0.4693 0.8207 0.14 Uiso 1 calc . .
H48C H 0.2197 0.589 0.7801 0.14 Uiso 1 calc . .
N1 N 0.53892(14) 0.24791(13) 0.30270(11) 0.0403(4) Uani 1 d . .
N2 N 0.47087(14) 0.29256(12) 0.19305(11) 0.0414(4) Uani 1 d . .
H2 H 0.4982 0.2955 0.1338 0.05 Uiso 1 calc . .
O41 O 0.12453(14) 0.33664(16) 0.25378(12) 0.0710(5) Uani 1 d . .
O5 O 0.50389(13) 0.22704(12) 0.48089(10) 0.0528(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.321(2) . ?
C3 C4 1.387(2) . ?
C3 C31 1.484(2) . ?
C4 C5 1.431(3) . ?
C4 C41 1.476(3) . ?
C5 O5 1.2502(19) . ?
C5 N1 1.390(2) . ?
C11 C16 1.385(3) . ?
C11 C12 1.389(2) . ?
C11 N1 1.415(2) . ?
C12 C13 1.373(3) . ?
C12 H12 0.93 . ?
C13 C14 1.372(3) . ?
C13 H13 0.93 . ?
C14 C15 1.374(3) . ?
C14 H14 0.93 . ?
C15 C16 1.376(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C41 O41 1.219(2) . ?
C41 C42 1.488(2) . ?
C42 C43 1.381(3) . ?
C42 C47 1.388(3) . ?
C47 C46 1.382(3) . ?
C47 H47 0.93 . ?
C46 C45 1.382(3) . ?
C46 H46 0.93 . ?
C45 C44 1.377(3) . ?
C45 C48 1.509(3) . ?
C44 C43 1.382(3) . ?
C44 H44 0.93 . ?
C43 H43 0.93 . ?
C48 H48A 0.96 . ?
C48 H48B 0.96 . ?
C48 H48C 0.96 . ?
N1 N2 1.3768(19) . ?
N2 H2 0.86 . ?

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
N2 C3 C4 109.09(15) . . ?
N2 C3 C31 119.80(15) . . ?
C4 C3 C31 131.01(16) . . ?
C3 C4 C5 107.03(15) . . ?
C3 C4 C41 122.79(16) . . ?
C5 C4 C41 129.98(15) . . ?
O5 C5 N1 121.71(16) . . ?
O5 C5 C4 132.69(16) . . ?
N1 C5 C4 105.56(14) . . ?
C16 C11 C12 119.59(17) . . ?
C16 C11 N1 120.57(16) . . ?
C12 C11 N1 119.83(16) . . ?
C13 C12 C11 119.62(18) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.88(18) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.49(19) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.66(19) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 119.74(18) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 119.57(16) . . ?
O41 C41 C42 119.65(17) . . ?
C4 C41 C42 120.73(15) . . ?
C43 C42 C47 118.68(17) . . ?
C43 C42 C41 122.77(16) . . ?
C47 C42 C41 118.50(17) . . ?
C46 C47 C42 119.9(2) . . ?
C46 C47 H47 120.1 . . ?
C42 C47 H47 120.1 . . ?
C47 C46 C45 121.8(2) . . ?
C47 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C44 C45 C46 117.81(19) . . ?
C44 C45 C48 121.6(2) . . ?
C46 C45 C48 120.6(2) . . ?
C45 C44 C43 121.2(2) . . ?
C45 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
C42 C43 C44 120.62(18) . . ?
C42 C43 H43 119.7 . . ?
C44 C43 H43 119.7 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N2 N1 C5 108.26(14) . . ?
N2 N1 C11 121.04(13) . . ?
C5 N1 C11 130.50(14) . . ?
C3 N2 N1 110.01(13) . . ?
C3 N2 H2 125 . . ?
N1 N2 H2 125 . . ?

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
N2 C3 C4 C5 -1.7(2) . . . . ?
C31 C3 C4 C5 -178.02(19) . . . . ?
N2 C3 C4 C41 -177.00(17) . . . . ?
C31 C3 C4 C41 6.7(3) . . . . ?
C3 C4 C5 O5 -177.4(2) . . . . ?
C41 C4 C5 O5 -2.6(3) . . . . ?
C3 C4 C5 N1 0.4(2) . . . . ?
C41 C4 C5 N1 175.28(18) . . . . ?
C16 C11 C12 C13 -1.7(3) . . . . ?
N1 C11 C12 C13 177.57(17) . . . . ?
C11 C12 C13 C14 1.9(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
N1 C11 C16 C15 -178.91(19) . . . . ?
C3 C4 C41 O41 31.0(3) . . . . ?
C5 C4 C41 O41 -143.2(2) . . . . ?
C3 C4 C41 C42 -146.58(18) . . . . ?
C5 C4 C41 C42 39.3(3) . . . . ?
O41 C41 C42 C43 -157.3(2) . . . . ?
C4 C41 C42 C43 20.3(3) . . . . ?
O41 C41 C42 C47 20.1(3) . . . . ?
C4 C41 C42 C47 -162.35(18) . . . . ?
C43 C42 C47 C46 -0.9(3) . . . . ?
C41 C42 C47 C46 -178.36(19) . . . . ?
C42 C47 C46 C45 1.2(3) . . . . ?
C47 C46 C45 C44 -0.3(3) . . . . ?
C47 C46 C45 C48 179.1(2) . . . . ?
C46 C45 C44 C43 -0.9(3) . . . . ?
C48 C45 C44 C43 179.7(2) . . . . ?
C47 C42 C43 C44 -0.3(3) . . . . ?
C41 C42 C43 C44 177.12(18) . . . . ?
C45 C44 C43 C42 1.2(3) . . . . ?
O5 C5 N1 N2 179.05(16) . . . . ?
C4 C5 N1 N2 0.92(19) . . . . ?
O5 C5 N1 C11 -6.3(3) . . . . ?
C4 C5 N1 C11 175.60(17) . . . . ?
C16 C11 N1 N2 149.00(17) . . . . ?
C12 C11 N1 N2 -30.3(2) . . . . ?
C16 C11 N1 C5 -25.1(3) . . . . ?
C12 C11 N1 C5 155.61(19) . . . . ?
C4 C3 N2 N1 2.3(2) . . . . ?
C31 C3 N2 N1 179.13(16) . . . . ?
C5 N1 N2 C3 -2.0(2) . . . . ?
C11 N1 N2 C3 -177.33(15) . . . . ?
C3 C4 C41 C42 -146.58(18) . . . . ?
C4 C41 C42 C43 20.3(3) . . . . ?
C5 N1 C11 C16 -25.1(3) . . . . ?

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
C12 H12 O5 0.93 2.58 3.374(3) 143 4_565
C16 H16 O5 0.93 2.43 2.956(3) 116.2 .
C31 H31B O41 0.96 2.58 3.022(3) 108 .
N2 H2 O5 0.86 1.87 2.696(2) 159.7 4_565



####################################################################### 
# 
# 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_exp_284_2
_database_code_depnum_ccdc_archive 'CCDC 1406734'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-27T16:37:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
_cell_length_a                   29.4285(19)
_cell_length_b                   8.8477(5)
_cell_length_c                   11.4839(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.468(5)
_cell_angle_gamma                90
_cell_volume                     2964.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      3.5640
_cell_measurement_theta_max      25.6080

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorles
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_F_000             1232
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_min  0.63255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_number            7006
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_ful 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_number_total             2718
_reflns_number_gt                2316
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0722P)²+2.6071P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2718
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.053
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.045

#----------------------------------------------------------------------------#
#                   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
C3 C 0.16308(6) 0.3835(2) 0.09222(15) 0.0194(4) Uani 1 d . .
C4 C 0.16385(6) 0.4296(2) 0.20872(16) 0.0193(4) Uani 1 d . .
C5 C 0.12328(6) 0.5167(2) 0.21542(15) 0.0185(4) Uani 1 d . .
C11 C 0.06323(6) 0.6116(2) 0.05546(15) 0.0201(4) Uani 1 d . .
C12 C 0.06470(6) 0.6934(2) -0.04745(16) 0.0256(4) Uani 1 d . .
H12 H 0.0905 0.6866 -0.0892 0.031 Uiso 1 calc . .
C13 C 0.02774(7) 0.7850(3) -0.08792(19) 0.0339(5) Uani 1 d . .
H13 H 0.0281 0.841 -0.1584 0.041 Uiso 1 calc . .
C14 C -0.00963(7) 0.7956(3) -0.0268(2) 0.0361(5) Uani 1 d . .
H14 H -0.0347 0.8593 -0.055 0.043 Uiso 1 calc . .
C15 C -0.01056(6) 0.7135(2) 0.07534(18) 0.0296(5) Uani 1 d . .
H15 H -0.0362 0.7213 0.1173 0.036 Uiso 1 calc . .
C16 C 0.02561(6) 0.6202(2) 0.11687(17) 0.0242(4) Uani 1 d . .
H16 H 0.0248 0.5626 0.1864 0.029 Uiso 1 calc . .
C31 C 0.19406(7) 0.2838(2) 0.03415(17) 0.0263(4) Uani 1 d . .
H31A H 0.1764 0.2317 -0.0321 0.039 Uiso 1 calc . .
H31B H 0.2081 0.2092 0.0907 0.039 Uiso 1 calc . .
H31C H 0.2181 0.3451 0.0056 0.039 Uiso 1 calc . .
C41 C 0.19948(6) 0.4062(2) 0.30962(15) 0.0190(4) Uani 1 d . .
C42 C 0.24871(6) 0.4203(2) 0.29193(15) 0.0195(4) Uani 1 d . .
C43 C 0.26292(6) 0.5020(2) 0.19894(16) 0.0227(4) Uani 1 d . .
H43 H 0.2407 0.5465 0.1418 0.027 Uiso 1 calc . .
C44 C 0.30894(6) 0.5187(2) 0.18915(17) 0.0252(4) Uani 1 d . .
H44 H 0.3179 0.5757 0.1258 0.03 Uiso 1 calc . .
C45 C 0.34250(6) 0.4534(2) 0.27078(17) 0.0247(4) Uani 1 d . .
C46 C 0.32837(6) 0.3716(2) 0.36333(17) 0.0255(4) Uani 1 d . .
H46 H 0.3507 0.3255 0.4194 0.031 Uiso 1 calc . .
C47 C 0.28235(6) 0.3564(2) 0.37494(16) 0.0219(4) Uani 1 d . .
H47 H 0.2735 0.3022 0.4398 0.026 Uiso 1 calc . .
C48 C 0.39252(7) 0.4728(3) 0.2588(2) 0.0378(5) Uani 1 d . .
H48A H 0.3981 0.4409 0.1802 0.057 Uiso 1 calc . .
H48B H 0.411 0.4108 0.3179 0.057 Uiso 1 calc . .
H48C H 0.4011 0.5793 0.2706 0.057 Uiso 1 calc . .
N1 N 0.10079(5) 0.51965(17) 0.10161(12) 0.0197(4) Uani 1 d . .
N2 N 0.12522(5) 0.43706(18) 0.02961(13) 0.0202(4) Uani 1 d . .
H2 H 0.1171 0.422 -0.046 0.024 Uiso 1 calc . .
O5 O 0.10821(4) 0.58581(15) 0.29807(11) 0.0236(3) Uani 1 d . .
O41 O 0.18884(4) 0.38276(15) 0.40794(11) 0.0243(3) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.332(2) . ?
C3 C4 1.396(3) . ?
C3 C31 1.487(3) . ?
C4 C5 1.432(2) . ?
C4 C41 1.473(2) . ?
C5 O5 1.257(2) . ?
C5 N1 1.386(2) . ?
C11 C12 1.391(3) . ?
C11 C16 1.390(3) . ?
C11 N1 1.419(2) . ?
C12 C13 1.387(3) . ?
C12 H12 0.95 . ?
C13 C14 1.383(3) . ?
C13 H13 0.95 . ?
C14 C15 1.383(3) . ?
C14 H14 0.95 . ?
C15 C16 1.382(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C41 O41 1.228(2) . ?
C41 C42 1.494(2) . ?
C42 C43 1.398(3) . ?
C42 C47 1.401(2) . ?
C43 C44 1.381(3) . ?
C43 H43 0.95 . ?
C44 C45 1.396(3) . ?
C44 H44 0.95 . ?
C45 C46 1.393(3) . ?
C45 C48 1.506(3) . ?
C46 C47 1.384(3) . ?
C46 H46 0.95 . ?
C47 H47 0.95 . ?
C48 H48A 0.98 . ?
C48 H48B 0.98 . ?
C48 H48C 0.98 . ?
N1 N2 1.374(2) . ?
N2 H2 0.88 . ?

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
N2 C3 C4 108.76(16) . . ?
N2 C3 C31 119.16(16) . . ?
C4 C3 C31 131.96(16) . . ?
C3 C4 C5 107.40(15) . . ?
C3 C4 C41 129.35(16) . . ?
C5 C4 C41 123.16(16) . . ?
O5 C5 N1 122.06(16) . . ?
O5 C5 C4 132.91(16) . . ?
N1 C5 C4 104.98(15) . . ?
C12 C11 C16 121.17(17) . . ?
C12 C11 N1 120.46(16) . . ?
C16 C11 N1 118.35(16) . . ?
C13 C12 C11 118.61(18) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 120.69(19) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.97(19) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C16 C15 C14 120.47(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 119.07(18) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 120.45(16) . . ?
O41 C41 C42 120.44(16) . . ?
C4 C41 C42 119.01(15) . . ?
C43 C42 C47 118.24(17) . . ?
C43 C42 C41 122.59(16) . . ?
C47 C42 C41 119.07(16) . . ?
C44 C43 C42 120.76(17) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 121.10(18) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C46 C45 C44 118.18(17) . . ?
C46 C45 C48 121.40(18) . . ?
C44 C45 C48 120.41(18) . . ?
C47 C46 C45 121.09(17) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C42 120.60(18) . . ?
C46 C47 H47 119.7 . . ?
C42 C47 H47 119.7 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N2 N1 C5 109.54(14) . . ?
N2 N1 C11 121.55(14) . . ?
C5 N1 C11 128.03(15) . . ?
C3 N2 N1 109.30(14) . . ?
C3 N2 H2 125.3 . . ?
N1 N2 H2 125.3 . . ?

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
N2 C3 C4 C5 0.2(2) . . . . ?
C31 C3 C4 C5 -175.65(19) . . . . ?
N2 C3 C4 C41 -176.38(18) . . . . ?
C31 C3 C4 C41 7.8(3) . . . . ?
C3 C4 C5 O5 -178.23(19) . . . . ?
C41 C4 C5 O5 -1.4(3) . . . . ?
C3 C4 C5 N1 -0.88(19) . . . . ?
C41 C4 C5 N1 175.94(16) . . . . ?
C16 C11 C12 C13 0.3(3) . . . . ?
N1 C11 C12 C13 -178.34(18) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C14 C15 C16 C11 0.9(3) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
N1 C11 C16 C15 177.70(17) . . . . ?
C3 C4 C41 O41 -143.54(19) . . . . ?
C5 C4 C41 O41 40.4(3) . . . . ?
C3 C4 C41 C42 40.0(3) . . . . ?
C5 C4 C41 C42 -136.08(18) . . . . ?
O41 C41 C42 C43 -154.23(18) . . . . ?
C4 C41 C42 C43 22.2(3) . . . . ?
O41 C41 C42 C47 22.2(3) . . . . ?
C4 C41 C42 C47 -161.38(17) . . . . ?
C47 C42 C43 C44 0.2(3) . . . . ?
C41 C42 C43 C44 176.64(17) . . . . ?
C42 C43 C44 C45 0.7(3) . . . . ?
C43 C44 C45 C46 -0.5(3) . . . . ?
C43 C44 C45 C48 -179.98(18) . . . . ?
C44 C45 C46 C47 -0.6(3) . . . . ?
C48 C45 C46 C47 178.86(19) . . . . ?
C45 C46 C47 C42 1.5(3) . . . . ?
C43 C42 C47 C46 -1.3(3) . . . . ?
C41 C42 C47 C46 -177.88(16) . . . . ?
O5 C5 N1 N2 178.98(16) . . . . ?
C4 C5 N1 N2 1.27(19) . . . . ?
O5 C5 N1 C11 9.7(3) . . . . ?
C4 C5 N1 C11 -167.98(17) . . . . ?
C12 C11 N1 N2 -38.3(2) . . . . ?
C16 C11 N1 N2 143.01(17) . . . . ?
C12 C11 N1 C5 129.8(2) . . . . ?
C16 C11 N1 C5 -48.9(3) . . . . ?
C4 C3 N2 N1 0.6(2) . . . . ?
C31 C3 N2 N1 177.07(16) . . . . ?
C5 N1 N2 C3 -1.2(2) . . . . ?
C11 N1 N2 C3 168.86(16) . . . . ?
C3 C4 C41 C42 40.0(3) . . . . ?
C4 C41 C42 C43 22.2(3) . . . . ?
C5 N1 C11 C16 -48.9(3) . . . . ?

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
N2 H2 O5 0.88 1.78 2.6487(19) 170.2 6_565




####################################################################### 
# 
# 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_new
_database_code_depnum_ccdc_archive 'CCDC 1406735'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-08-25 downloaded from the CCDC.
;

_audit_creation_date             2015-02-27T16:30:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
_cell_length_a                   29.4372(12)
_cell_length_b                   9.0498(4)
_cell_length_c                   11.4930(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.479(4)
_cell_angle_gamma                90
_cell_volume                     3035.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      3.411
_cell_measurement_theta_max      26.309

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colorles
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1232
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.59122
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_orient_matrix_ub_11      0.0168934
_diffrn_orient_matrix_ub_12      0.0551186
_diffrn_orient_matrix_ub_13      0.0149241
_diffrn_orient_matrix_ub_21      0.0165028
_diffrn_orient_matrix_ub_22      -0.0556848
_diffrn_orient_matrix_ub_23      0.0169336
_diffrn_orient_matrix_ub_31      0.0057549
_diffrn_orient_matrix_ub_32      -0.0020793
_diffrn_orient_matrix_ub_33      -0.057998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_number            7848
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.792
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_ful 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_number_total             3100
_reflns_number_gt                2377
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
        (compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

#----------------------------------------------------------------------------#
#                   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)+(0.0722P)²+2.6071P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.148
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   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
C3 C 0.16234(6) 0.3850(2) 0.09073(16) 0.0347(4) Uani 1 d . .
C4 C 0.16322(6) 0.4292(2) 0.20713(15) 0.0332(4) Uani 1 d . .
C5 C 0.12305(6) 0.5156(2) 0.21371(14) 0.0330(4) Uani 1 d . .
C11 C 0.06354(6) 0.6119(2) 0.05434(15) 0.0343(4) Uani 1 d . .
C12 C 0.06532(7) 0.6914(3) -0.04769(18) 0.0481(5) Uani 1 d . .
H12 H 0.0906 0.6843 -0.0883 0.058 Uiso 1 calc . .
C13 C 0.02880(9) 0.7818(3) -0.0882(2) 0.0666(7) Uani 1 d . .
H13 H 0.0294 0.8353 -0.157 0.08 Uiso 1 calc . .
C14 C -0.00837(9) 0.7934(3) -0.0278(3) 0.0700(8) Uani 1 d . .
H14 H -0.0326 0.8552 -0.0556 0.084 Uiso 1 calc . .
C15 C -0.00976(7) 0.7138(3) 0.0736(2) 0.0577(7) Uani 1 d . .
H15 H -0.0349 0.7222 0.1145 0.069 Uiso 1 calc . .
C16 C 0.02593(7) 0.6220(3) 0.11449(18) 0.0443(5) Uani 1 d . .
H16 H 0.0248 0.5669 0.1824 0.053 Uiso 1 calc . .
C31 C 0.19269(8) 0.2858(3) 0.03292(19) 0.0510(6) Uani 1 d . .
H31A H 0.1754 0.2398 -0.0339 0.076 Uiso 1 calc . .
H31B H 0.2051 0.2112 0.0874 0.076 Uiso 1 calc . .
H31C H 0.2173 0.3423 0.0079 0.076 Uiso 1 calc . .
C41 C 0.19868(6) 0.4042(2) 0.30758(15) 0.0337(4) Uani 1 d . .
C42 C 0.24791(6) 0.4188(2) 0.29099(15) 0.0338(4) Uani 1 d . .
C43 C 0.26225(7) 0.5005(2) 0.19959(17) 0.0418(5) Uani 1 d . .
H43 H 0.2406 0.5445 0.1442 0.05 Uiso 1 calc . .
C44 C 0.30813(7) 0.5165(2) 0.19057(19) 0.0473(5) Uani 1 d . .
H44 H 0.317 0.5726 0.1295 0.057 Uiso 1 calc . .
C45 C 0.34151(7) 0.4512(2) 0.2703(2) 0.0472(5) Uani 1 d . .
C46 C 0.32712(7) 0.3700(3) 0.36117(19) 0.0481(5) Uani 1 d . .
H46 H 0.3488 0.325 0.4158 0.058 Uiso 1 calc . .
C47 C 0.28137(7) 0.3546(2) 0.37202(17) 0.0391(5) Uani 1 d . .
H47 H 0.2727 0.3006 0.4343 0.047 Uiso 1 calc . .
C48 C 0.39161(8) 0.4695(4) 0.2587(3) 0.0777(9) Uani 1 d . .
H48A H 0.3961 0.4582 0.178 0.117 Uiso 1 calc . .
H48B H 0.4091 0.3959 0.3052 0.117 Uiso 1 calc . .
H48C H 0.4016 0.5661 0.2856 0.117 Uiso 1 calc . .
N1 N 0.10067(5) 0.52057(19) 0.10006(12) 0.0353(4) Uani 1 d . .
N2 N 0.12489(5) 0.43877(19) 0.02841(13) 0.0372(4) Uani 1 d . .
H2 H 0.117 0.4246 -0.0454 0.045 Uiso 1 calc . .
O5 O 0.10826(5) 0.58337(17) 0.29619(10) 0.0440(4) Uani 1 d . .
O41 O 0.18793(5) 0.37930(18) 0.40523(11) 0.0465(4) Uani 1 d . .



#----------------------------------------------------------------------------#
#                   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
C3 N2 1.326(2) . ?
C3 C4 1.393(2) . ?
C3 C31 1.483(3) . ?
C4 C5 1.428(3) . ?
C4 C41 1.469(3) . ?
C5 O5 1.254(2) . ?
C5 N1 1.385(2) . ?
C11 C16 1.383(3) . ?
C11 C12 1.383(3) . ?
C11 N1 1.416(2) . ?
C12 C13 1.382(3) . ?
C12 H12 0.93 . ?
C13 C14 1.374(4) . ?
C13 H13 0.93 . ?
C14 C15 1.375(4) . ?
C14 H14 0.93 . ?
C15 C16 1.373(3) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C31 H31A 0.96 . ?
C31 H31B 0.96 . ?
C31 H31C 0.96 . ?
C41 O41 1.226(2) . ?
C41 C42 1.492(3) . ?
C42 C47 1.392(3) . ?
C42 C43 1.394(3) . ?
C43 C44 1.375(3) . ?
C43 H43 0.93 . ?
C44 C45 1.386(3) . ?
C44 H44 0.93 . ?
C45 C46 1.388(3) . ?
C45 C48 1.507(3) . ?
C46 C47 1.376(3) . ?
C46 H46 0.93 . ?
C47 H47 0.93 . ?
C48 H48A 0.96 . ?
C48 H48B 0.96 . ?
C48 H48C 0.96 . ?
N1 N2 1.374(2) . ?
N2 H2 0.86 . ?

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
N2 C3 C4 108.89(16) . . ?
N2 C3 C31 119.13(17) . . ?
C4 C3 C31 131.81(18) . . ?
C3 C4 C5 107.21(16) . . ?
C3 C4 C41 129.26(17) . . ?
C5 C4 C41 123.44(16) . . ?
O5 C5 N1 121.86(16) . . ?
O5 C5 C4 132.80(16) . . ?
N1 C5 C4 105.27(15) . . ?
C16 C11 C12 120.70(19) . . ?
C16 C11 N1 118.89(17) . . ?
C12 C11 N1 120.40(17) . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 120 . . ?
C14 C15 H15 120 . . ?
C15 C16 C11 119.7(2) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O41 C41 C4 120.40(17) . . ?
O41 C41 C42 120.26(17) . . ?
C4 C41 C42 119.23(15) . . ?
C47 C42 C43 117.93(18) . . ?
C47 C42 C41 119.47(16) . . ?
C43 C42 C41 122.54(17) . . ?
C44 C43 C42 120.63(19) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 121.59(19) . . ?
C43 C44 H44 119.2 . . ?
C45 C44 H44 119.2 . . ?
C44 C45 C46 117.63(19) . . ?
C44 C45 C48 120.8(2) . . ?
C46 C45 C48 121.5(2) . . ?
C47 C46 C45 121.4(2) . . ?
C47 C46 H46 119.3 . . ?
C45 C46 H46 119.3 . . ?
C46 C47 C42 120.86(19) . . ?
C46 C47 H47 119.6 . . ?
C42 C47 H47 119.6 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N2 N1 C5 109.12(14) . . ?
N2 N1 C11 121.86(14) . . ?
C5 N1 C11 128.21(15) . . ?
C3 N2 N1 109.49(14) . . ?
C3 N2 H2 125.3 . . ?
N1 N2 H2 125.3 . . ?

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
N2 C3 C4 C5 0.1(2) . . . . ?
C31 C3 C4 C5 -174.9(2) . . . . ?
N2 C3 C4 C41 -176.42(19) . . . . ?
C31 C3 C4 C41 8.6(4) . . . . ?
C3 C4 C5 O5 -178.0(2) . . . . ?
C41 C4 C5 O5 -1.2(3) . . . . ?
C3 C4 C5 N1 -1.0(2) . . . . ?
C41 C4 C5 N1 175.73(18) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
N1 C11 C12 C13 -178.6(2) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.5(5) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C11 1.1(4) . . . . ?
C12 C11 C16 C15 -1.0(3) . . . . ?
N1 C11 C16 C15 177.8(2) . . . . ?
C3 C4 C41 O41 -142.7(2) . . . . ?
C5 C4 C41 O41 41.3(3) . . . . ?
C3 C4 C41 C42 41.1(3) . . . . ?
C5 C4 C41 C42 -134.89(19) . . . . ?
O41 C41 C42 C47 22.9(3) . . . . ?
C4 C41 C42 C47 -160.97(18) . . . . ?
O41 C41 C42 C43 -154.23(19) . . . . ?
C4 C41 C42 C43 21.9(3) . . . . ?
C47 C42 C43 C44 0.0(3) . . . . ?
C41 C42 C43 C44 177.08(19) . . . . ?
C42 C43 C44 C45 0.9(3) . . . . ?
C43 C44 C45 C46 -0.8(3) . . . . ?
C43 C44 C45 C48 179.7(2) . . . . ?
C44 C45 C46 C47 0.0(3) . . . . ?
C48 C45 C46 C47 179.4(2) . . . . ?
C45 C46 C47 C42 0.8(3) . . . . ?
C43 C42 C47 C46 -0.8(3) . . . . ?
C41 C42 C47 C46 -177.99(19) . . . . ?
O5 C5 N1 N2 178.96(17) . . . . ?
C4 C5 N1 N2 1.6(2) . . . . ?
O5 C5 N1 C11 9.2(3) . . . . ?
C4 C5 N1 C11 -168.14(18) . . . . ?
C16 C11 N1 N2 142.81(19) . . . . ?
C12 C11 N1 N2 -38.3(3) . . . . ?
C16 C11 N1 C5 -48.6(3) . . . . ?
C12 C11 N1 C5 130.2(2) . . . . ?
C4 C3 N2 N1 0.9(2) . . . . ?
C31 C3 N2 N1 176.68(18) . . . . ?
C5 N1 N2 C3 -1.6(2) . . . . ?
C11 N1 N2 C3 168.90(17) . . . . ?
C3 C4 C41 C42 41.1(3) . . . . ?
C4 C41 C42 C43 21.9(3) . . . . ?
C5 N1 C11 C16 -48.6(3) . . . . ?

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
N2 H2 O5 0.86 1.81 2.6576(19) 170.2 6_565




