# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I-P
_database_code_depnum_ccdc_archive 'CCDC 1409997'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 N3 O'
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.810(5)
_cell_length_b                   9.256(5)
_cell_length_c                   26.893(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.997(5)
_cell_angle_gamma                90
_cell_volume                     1440.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.9765
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_process_details   Multi-Scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11010
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2668
_reflns_number_gt                2087
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         2668
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1268
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2380(3) 0.25432(19) 0.59203(7) 0.0180(4) Uani 1 1 d . . .
C2 C -0.2610(3) 0.30246(19) 0.64045(7) 0.0197(5) Uani 1 1 d . . .
H2 H -0.3852 0.2740 0.6577 0.024 Uiso 1 1 calc R . .
C3 C -0.0934(3) 0.3936(2) 0.66170(7) 0.0204(5) Uani 1 1 d . . .
H3 H -0.1025 0.4259 0.6942 0.024 Uiso 1 1 calc R . .
C4 C 0.0907(4) 0.4384(2) 0.63526(7) 0.0229(5) Uani 1 1 d . . .
H4 H 0.2017 0.5003 0.6504 0.027 Uiso 1 1 calc R . .
C5 C 0.1102(3) 0.3922(2) 0.58693(7) 0.0209(5) Uani 1 1 d . . .
H5 H 0.2323 0.4234 0.5695 0.025 Uiso 1 1 calc R . .
C6 C -0.0547(3) 0.29873(19) 0.56489(7) 0.0178(4) Uani 1 1 d . . .
C7 C -0.0860(3) 0.2260(2) 0.51676(7) 0.0184(4) Uani 1 1 d . . .
C8 C -0.2835(3) 0.1422(2) 0.51807(7) 0.0202(5) Uani 1 1 d . . .
H8 H -0.3447 0.0829 0.4923 0.024 Uiso 1 1 calc R . .
C9 C 0.0640(3) 0.2460(2) 0.47837(7) 0.0175(4) Uani 1 1 d . . .
C10 C 0.0690(3) 0.19076(19) 0.43129(7) 0.0172(4) Uani 1 1 d . . .
C11 C -0.0817(3) 0.08744(19) 0.40297(7) 0.0166(4) Uani 1 1 d . . .
C12 C 0.2402(3) 0.23084(19) 0.39784(7) 0.0173(4) Uani 1 1 d . . .
C13 C 0.4329(3) 0.3348(2) 0.40771(7) 0.0212(5) Uani 1 1 d . . .
H13A H 0.5196 0.3406 0.3790 0.032 Uiso 1 1 calc R . .
H13B H 0.5322 0.3027 0.4360 0.032 Uiso 1 1 calc R . .
H13C H 0.3718 0.4283 0.4146 0.032 Uiso 1 1 calc R . .
C14 C -0.0537(3) -0.01118(19) 0.31549(7) 0.0171(4) Uani 1 1 d . . .
C15 C -0.2679(3) -0.0786(2) 0.30975(7) 0.0209(5) Uani 1 1 d . . .
H15 H -0.3748 -0.0640 0.3330 0.025 Uiso 1 1 calc R . .
C16 C -0.3208(4) -0.1680(2) 0.26889(7) 0.0224(5) Uani 1 1 d . . .
H16 H -0.4633 -0.2144 0.2652 0.027 Uiso 1 1 calc R . .
C17 C -0.1651(3) -0.1890(2) 0.23360(7) 0.0211(5) Uani 1 1 d . . .
H17 H -0.2015 -0.2498 0.2065 0.025 Uiso 1 1 calc R . .
C18 C 0.0450(3) -0.1187(2) 0.23887(7) 0.0213(5) Uani 1 1 d . . .
H18 H 0.1497 -0.1314 0.2150 0.026 Uiso 1 1 calc R . .
C19 C 0.1014(3) -0.0296(2) 0.27930(7) 0.0191(5) Uani 1 1 d . . .
H19 H 0.2428 0.0180 0.2824 0.023 Uiso 1 1 calc R . .
N1 N -0.3735(3) 0.15933(17) 0.56235(6) 0.0206(4) Uani 1 1 d . . .
N2 N 0.0100(3) 0.07809(16) 0.35730(5) 0.0168(4) Uani 1 1 d . . .
N3 N 0.2076(3) 0.16527(16) 0.35495(6) 0.0189(4) Uani 1 1 d . . .
O1 O -0.2522(2) 0.02125(13) 0.41535(5) 0.0206(4) Uani 1 1 d . . .
H1N1 H -0.503(4) 0.115(2) 0.5719(7) 0.022(5) Uiso 1 1 d . . .
H9 H 0.198(3) 0.318(2) 0.4875(7) 0.019(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.386(3) . ?
C1 C2 1.394(2) . ?
C1 C6 1.404(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(2) . ?
C7 C8 1.388(3) . ?
C7 C9 1.420(3) . ?
C8 N1 1.351(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 1.04(2) . ?
C10 C12 1.446(3) . ?
C10 C11 1.465(3) . ?
C11 O1 1.235(2) . ?
C11 N2 1.383(2) . ?
C12 N3 1.303(2) . ?
C12 C13 1.483(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.389(3) . ?
C14 C19 1.393(3) . ?
C14 N2 1.418(2) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
N1 H1N1 0.91(2) . ?
N2 N3 1.409(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
N1 C1 C2 130.18(18) . . ?
N1 C1 C6 107.75(16) . . ?
C2 C1 C6 122.06(18) . . ?
C3 C2 C1 117.55(18) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 121.09(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.04(19) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.02(18) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 119.21(17) . . ?
C5 C6 C7 134.22(18) . . ?
C1 C6 C7 106.55(17) . . ?
C8 C7 C9 130.71(18) . . ?
C8 C7 C6 106.01(16) . . ?
C9 C7 C6 123.28(18) . . ?
N1 C8 C7 109.92(17) . . ?
N1 C8 H8 125.0 . . ?
C7 C8 H8 125.0 . . ?
C10 C9 C7 133.47(19) . . ?
C10 C9 H9 112.6(10) . . ?
C7 C9 H9 114.0(10) . . ?
C9 C10 C12 123.43(18) . . ?
C9 C10 C11 131.70(18) . . ?
C12 C10 C11 104.86(16) . . ?
O1 C11 N2 126.06(17) . . ?
O1 C11 C10 129.87(17) . . ?
N2 C11 C10 104.07(15) . . ?
N3 C12 C10 112.12(17) . . ?
N3 C12 C13 120.68(16) . . ?
C10 C12 C13 127.20(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.67(17) . . ?
C15 C14 N2 121.29(16) . . ?
C19 C14 N2 119.04(17) . . ?
C16 C15 C14 119.38(18) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.94(19) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 119.35(18) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.62(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 119.99(18) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C8 N1 C1 109.77(17) . . ?
C8 N1 H1N1 126.0(13) . . ?
C1 N1 H1N1 124.2(12) . . ?
C11 N2 N3 112.50(14) . . ?
C11 N2 C14 130.25(16) . . ?
N3 N2 C14 117.08(14) . . ?
C12 N3 N2 106.44(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 177.39(18) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C4 C5 C6 C7 -177.8(2) . . . . ?
N1 C1 C6 C5 -178.47(17) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
N1 C1 C6 C7 0.3(2) . . . . ?
C2 C1 C6 C7 179.37(17) . . . . ?
C5 C6 C7 C8 178.0(2) . . . . ?
C1 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C9 -2.8(3) . . . . ?
C1 C6 C7 C9 178.76(17) . . . . ?
C9 C7 C8 N1 -178.6(2) . . . . ?
C6 C7 C8 N1 0.6(2) . . . . ?
C8 C7 C9 C10 -1.0(4) . . . . ?
C6 C7 C9 C10 179.98(19) . . . . ?
C7 C9 C10 C12 178.45(19) . . . . ?
C7 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 O1 -1.5(4) . . . . ?
C12 C10 C11 O1 179.31(18) . . . . ?
C9 C10 C11 N2 178.61(19) . . . . ?
C12 C10 C11 N2 -0.53(19) . . . . ?
C9 C10 C12 N3 -179.23(17) . . . . ?
C11 C10 C12 N3 0.0(2) . . . . ?
C9 C10 C12 C13 -0.2(3) . . . . ?
C11 C10 C12 C13 179.04(17) . . . . ?
C19 C14 C15 C16 2.5(3) . . . . ?
N2 C14 C15 C16 -178.37(17) . . . . ?
C14 C15 C16 C17 -1.0(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C14 0.6(3) . . . . ?
C15 C14 C19 C18 -2.3(3) . . . . ?
N2 C14 C19 C18 178.52(16) . . . . ?
C7 C8 N1 C1 -0.4(2) . . . . ?
C2 C1 N1 C8 -178.93(19) . . . . ?
C6 C1 N1 C8 0.1(2) . . . . ?
O1 C11 N2 N3 -178.97(17) . . . . ?
C10 C11 N2 N3 0.88(19) . . . . ?
O1 C11 N2 C14 -4.0(3) . . . . ?
C10 C11 N2 C14 175.82(17) . . . . ?
C15 C14 N2 C11 18.2(3) . . . . ?
C19 C14 N2 C11 -162.63(18) . . . . ?
C15 C14 N2 N3 -167.05(16) . . . . ?
C19 C14 N2 N3 12.1(2) . . . . ?
C10 C12 N3 N2 0.5(2) . . . . ?
C13 C12 N3 N2 -178.59(15) . . . . ?
C11 N2 N3 C12 -0.9(2) . . . . ?
C14 N2 N3 C12 -176.56(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_3FP
_database_code_depnum_ccdc_archive 'CCDC 1432605'
_audit_update_record             
;
2015-10-22 deposited with the CCDC.
2015-12-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.870(5)
_cell_length_b                   8.298(3)
_cell_length_c                   11.843(5)
_cell_angle_alpha                85.806(4)
_cell_angle_beta                 80.900(5)
_cell_angle_gamma                89.987(5)
_cell_volume                     761.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX'
_diffrn_measurement_method       /w-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9548
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2832
_reflns_number_gt                2314
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45 ( Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 2.1e'
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.2569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.41790(19) 0.53049(18) 0.79349(13) 0.0185(3) Uani 1 1 d . . .
H1 H 0.4242 0.6049 0.7303 0.022 Uiso 1 1 calc R . .
C2 C 0.28442(19) 0.44469(18) 0.97953(12) 0.0171(3) Uani 1 1 d . . .
C3 C 0.1578(2) 0.47496(19) 1.07064(13) 0.0206(4) Uani 1 1 d . . .
H3 H 0.0922 0.5680 1.0684 0.025 Uiso 1 1 calc R . .
C4 C 0.1309(2) 0.36462(19) 1.16469(13) 0.0229(4) Uani 1 1 d . . .
H4 H 0.0449 0.3820 1.2260 0.027 Uiso 1 1 calc R . .
C5 C 0.2322(2) 0.22702(19) 1.16818(14) 0.0242(4) Uani 1 1 d . . .
H5 H 0.2127 0.1524 1.2315 0.029 Uiso 1 1 calc R . .
C6 C 0.3607(2) 0.20097(19) 1.07852(14) 0.0219(4) Uani 1 1 d . . .
H6 H 0.4291 0.1100 1.0824 0.026 Uiso 1 1 calc R . .
C7 C 0.38932(19) 0.30989(18) 0.98194(13) 0.0180(3) Uani 1 1 d . . .
C8 C 0.52512(19) 0.28624(17) 0.88502(13) 0.0180(3) Uani 1 1 d . . .
C9 C 0.52747(19) 0.40439(18) 0.78557(13) 0.0174(3) Uani 1 1 d . . .
C10 C 0.64487(19) 0.36989(18) 0.68346(13) 0.0187(3) Uani 1 1 d . . .
C11 C 0.69577(19) 0.45137(18) 0.58090(13) 0.0184(3) Uani 1 1 d . . .
C12 C 0.66141(19) 0.61825(18) 0.53677(13) 0.0192(3) Uani 1 1 d . . .
C13 C 0.80886(19) 0.38557(18) 0.48650(13) 0.0192(3) Uani 1 1 d . . .
C14 C 0.8758(2) 0.21762(19) 0.48319(14) 0.0234(4) Uani 1 1 d . . .
H14A H 0.9474 0.2060 0.4108 0.035 Uiso 1 1 calc R . .
H14B H 0.7810 0.1424 0.4926 0.035 Uiso 1 1 calc R . .
H14C H 0.9420 0.1962 0.5440 0.035 Uiso 1 1 calc R . .
C15 C 0.7706(2) 0.76520(18) 0.34467(13) 0.0196(3) Uani 1 1 d . . .
C16 C 0.9082(2) 0.77038(19) 0.25415(13) 0.0221(4) Uani 1 1 d . . .
H16 H 0.9899 0.6892 0.2502 0.027 Uiso 1 1 calc R . .
C17 C 0.9221(2) 0.8972(2) 0.17038(14) 0.0271(4) Uani 1 1 d . . .
H17 H 1.0143 0.9014 0.1104 0.032 Uiso 1 1 calc R . .
C18 C 0.8004(2) 1.0177(2) 0.17492(14) 0.0270(4) Uani 1 1 d . . .
H18 H 0.8088 1.1012 0.1174 0.032 Uiso 1 1 calc R . .
C19 C 0.6660(2) 1.01272(19) 0.26592(14) 0.0240(4) Uani 1 1 d . . .
H19 H 0.5848 1.0944 0.2696 0.029 Uiso 1 1 calc R . .
C20 C 0.6504(2) 0.88829(18) 0.35157(13) 0.0206(3) Uani 1 1 d . . .
H20 H 0.5606 0.8871 0.4130 0.025 Uiso 1 1 calc R . .
N1 N 0.75435(16) 0.63112(15) 0.42760(11) 0.0192(3) Uani 1 1 d . . .
N2 N 0.84274(16) 0.48844(15) 0.39826(11) 0.0202(3) Uani 1 1 d . . .
O1 O 0.30107(13) 0.55613(12) 0.88569(9) 0.0196(3) Uani 1 1 d . . .
O2 O 0.63154(14) 0.17834(12) 0.88672(9) 0.0251(3) Uani 1 1 d . . .
O3 O 0.57425(14) 0.72457(13) 0.58315(9) 0.0250(3) Uani 1 1 d . . .
H10 H 0.695(2) 0.261(2) 0.6928(13) 0.019(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3414(18) . ?
C1 C9 1.355(2) . ?
C1 H1 0.9300 . ?
C2 O1 1.3823(18) . ?
C2 C3 1.385(2) . ?
C2 C7 1.391(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.464(2) . ?
C8 O2 1.2272(18) . ?
C8 C9 1.474(2) . ?
C9 C10 1.447(2) . ?
C10 C11 1.349(2) . ?
C10 H10 0.994(16) . ?
C11 C13 1.454(2) . ?
C11 C12 1.484(2) . ?
C12 O3 1.2256(19) . ?
C12 N1 1.378(2) . ?
C13 N2 1.294(2) . ?
C13 C14 1.491(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C20 1.390(2) . ?
C15 C16 1.396(2) . ?
C15 N1 1.421(2) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 N2 1.4106(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
O1 C1 C9 124.91(14) . . ?
O1 C1 H1 117.5 . . ?
C9 C1 H1 117.5 . . ?
O1 C2 C3 116.27(13) . . ?
O1 C2 C7 121.65(13) . . ?
C3 C2 C7 122.08(14) . . ?
C4 C3 C2 118.80(15) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 120.15(15) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.39(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.54(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.00(14) . . ?
C2 C7 C8 119.96(14) . . ?
C6 C7 C8 122.04(14) . . ?
O2 C8 C7 122.82(14) . . ?
O2 C8 C9 122.17(14) . . ?
C7 C8 C9 114.99(13) . . ?
C1 C9 C10 125.01(14) . . ?
C1 C9 C8 119.28(14) . . ?
C10 C9 C8 115.64(13) . . ?
C11 C10 C9 134.04(15) . . ?
C11 C10 H10 115.2(9) . . ?
C9 C10 H10 110.7(9) . . ?
C10 C11 C13 124.01(14) . . ?
C10 C11 C12 131.75(14) . . ?
C13 C11 C12 104.22(13) . . ?
O3 C12 N1 126.01(14) . . ?
O3 C12 C11 130.24(14) . . ?
N1 C12 C11 103.74(13) . . ?
N2 C13 C11 112.42(14) . . ?
N2 C13 C14 120.99(14) . . ?
C11 C13 C14 126.52(14) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.09(15) . . ?
C20 C15 N1 120.98(14) . . ?
C16 C15 N1 118.92(14) . . ?
C17 C16 C15 119.55(15) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.69(15) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.29(15) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 121.15(15) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 119.19(15) . . ?
C19 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?
C12 N1 N2 112.96(12) . . ?
C12 N1 C15 128.90(13) . . ?
N2 N1 C15 118.13(12) . . ?
C13 N2 N1 106.65(12) . . ?
C1 O1 C2 118.92(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 177.49(13) . . . . ?
C7 C2 C3 C4 -2.5(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
O1 C2 C7 C6 -178.17(13) . . . . ?
C3 C2 C7 C6 1.9(2) . . . . ?
O1 C2 C7 C8 2.0(2) . . . . ?
C3 C2 C7 C8 -177.93(14) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
C5 C6 C7 C8 179.88(14) . . . . ?
C2 C7 C8 O2 173.01(14) . . . . ?
C6 C7 C8 O2 -6.8(2) . . . . ?
C2 C7 C8 C9 -5.6(2) . . . . ?
C6 C7 C8 C9 174.60(13) . . . . ?
O1 C1 C9 C10 175.23(13) . . . . ?
O1 C1 C9 C8 -1.7(2) . . . . ?
O2 C8 C9 C1 -173.16(14) . . . . ?
C7 C8 C9 C1 5.5(2) . . . . ?
O2 C8 C9 C10 9.6(2) . . . . ?
C7 C8 C9 C10 -171.74(12) . . . . ?
C1 C9 C10 C11 9.8(3) . . . . ?
C8 C9 C10 C11 -173.21(16) . . . . ?
C9 C10 C11 C13 -175.40(15) . . . . ?
C9 C10 C11 C12 6.6(3) . . . . ?
C10 C11 C12 O3 -1.3(3) . . . . ?
C13 C11 C12 O3 -179.56(16) . . . . ?
C10 C11 C12 N1 177.87(16) . . . . ?
C13 C11 C12 N1 -0.41(15) . . . . ?
C10 C11 C13 N2 -178.22(14) . . . . ?
C12 C11 C13 N2 0.23(17) . . . . ?
C10 C11 C13 C14 4.9(2) . . . . ?
C12 C11 C13 C14 -176.70(14) . . . . ?
C20 C15 C16 C17 -1.2(2) . . . . ?
N1 C15 C16 C17 177.60(14) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
C18 C19 C20 C15 -1.0(2) . . . . ?
C16 C15 C20 C19 2.0(2) . . . . ?
N1 C15 C20 C19 -176.77(13) . . . . ?
O3 C12 N1 N2 179.67(14) . . . . ?
C11 C12 N1 N2 0.48(16) . . . . ?
O3 C12 N1 C15 -0.5(3) . . . . ?
C11 C12 N1 C15 -179.66(14) . . . . ?
C20 C15 N1 C12 -20.0(2) . . . . ?
C16 C15 N1 C12 161.19(15) . . . . ?
C20 C15 N1 N2 159.82(13) . . . . ?
C16 C15 N1 N2 -19.0(2) . . . . ?
C11 C13 N2 N1 0.05(17) . . . . ?
C14 C13 N2 N1 177.17(13) . . . . ?
C12 N1 N2 C13 -0.35(17) . . . . ?
C15 N1 N2 C13 179.77(13) . . . . ?
C9 C1 O1 C2 -2.3(2) . . . . ?
C3 C2 O1 C1 -177.94(13) . . . . ?
C7 C2 O1 C1 2.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
