# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429526'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.0110(9)
_cell_length_b                   6.9999(6)
_cell_length_c                   11.5760(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.360(10)
_cell_angle_gamma                90
_cell_volume                     795.31(12)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m '
_symmetry_space_group_name_Hall  '-P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C14.67 N1.33 O1.33 
# Dc =      1.35 Fooo =    332.00 Mu =      7.37 M =    162.13
# Found Formula = C12.67 H10 N2 O1.33 
# Dc =      1.33 FOOO =    332.00 Mu =      7.15 M =    158.67

_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_moiety         'C19 H15 N3 O2'
_chemical_compound_source        ?
_chemical_formula_weight         317.34


_cell_measurement_reflns_used    5464
_cell_measurement_theta_min      3.8918
_cell_measurement_theta_max      66.3129
_cell_measurement_temperature    100

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_min          0.094
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_max          0.511

_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.715

# Sheldrick geometric approximatio 0.78 0.93 
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            8943
_reflns_number_total             1533
_diffrn_reflns_av_R_equivalents  0.045
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1533 
# Theoretical number of reflections is about 2799 


_diffrn_reflns_theta_min         3.895
_diffrn_reflns_theta_max         66.416
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        66.416
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.41
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.69


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         1533
_refine_ls_number_restraints     14
_refine_ls_number_parameters     150
_oxford_refine_ls_R_factor_ref   0.0465
_refine_ls_wR_factor_ref         0.1059
_refine_ls_goodness_of_fit_ref   0.9391
_refine_ls_shift/su_max          0.0032352
_refine_ls_shift/su_mean         0.0000351


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1533
_refine_ls_R_factor_all          0.0465
_refine_ls_wR_factor_all         0.1059

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1448
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_gt          0.1043

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.147E+04 0.247E+04 0.147E+04 588. 127. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.47818(14) 0.7500 -0.30866(12) 0.0201 1.0000 Uani S T . . . .
C2 C 0.6051(2) 0.7500 -0.24536(18) 0.0179 1.0000 Uani S T . . . .
C3 C 0.6011(2) 0.7500 -0.12130(17) 0.0190 1.0000 Uani S T . . . .
C4 C 0.4686(2) 0.7500 -0.10764(17) 0.0192 1.0000 Uani S T . . . .
C5 C 0.3778(2) 0.7500 -0.22930(17) 0.0191 1.0000 Uani S T . . . .
C6 C 0.29319(14) 0.5696(2) -0.25790(12) 0.0233 1.0000 Uani . . . . . .
H63 H 0.3490 0.4570 -0.2374 0.0344 1.0000 Uiso R . . . . .
H62 H 0.2549 0.5675 -0.3420 0.0327 1.0000 Uiso R . . . . .
H61 H 0.2207 0.5685 -0.2132 0.0331 1.0000 Uiso R . . . . .
C7 C 0.4303(2) 0.750000(7) 0.00545(19) 0.0242 1.0000 Uani S T . . . .
C8 C 0.3023(2) 0.750000(7) 0.02493(19) 0.0235 1.0000 Uani S T . . . .
C9 C 0.2634(2) 0.7500 0.14032(19) 0.0237 1.0000 Uani S T . . . .
C10 C 0.3574(2) 0.750000(7) 0.2489(2) 0.0241 1.0000 Uani S T . . . .
C11 C 0.3138(2) 0.750000(7) 0.35523(19) 0.0218 1.0000 Uani S T . . . .
C12 C 0.1741(2) 0.7500 0.35490(17) 0.0192 1.0000 Uani S T . . . .
O13 O 0.13804(14) 0.7500 0.46261(12) 0.0227 1.0000 Uani S T . . . .
C14 C -0.0039(2) 0.750000(7) 0.4652(2) 0.0288 1.0000 Uani S T . . . .
H142 H -0.0462 0.6356 0.4268 0.0418 1.0000 Uiso R . . . . .
H143 H -0.0130 0.7500 0.5480 0.0431 1.0000 Uiso RS . . . . .
C15 C 0.0805(2) 0.750000(7) 0.24810(18) 0.0234 1.0000 Uani S T . . . .
C16 C 0.1260(2) 0.750000(7) 0.14316(19) 0.0262 1.0000 Uani S T . . . .
H161 H 0.0603 0.7500 0.0703 0.0317 1.0000 Uiso RS . . . . .
H151 H -0.0159 0.7500 0.2477 0.0290 1.0000 Uiso RS . . . . .
H111 H 0.3742 0.7500 0.4278 0.0254 1.0000 Uiso RS . . . . .
H101 H 0.4527 0.7500 0.2529 0.0295 1.0000 Uiso RS . . . . .
H81 H 0.2305 0.7500 -0.0449 0.0285 1.0000 Uiso RS . . . . .
H71 H 0.5018 0.7500 0.0763 0.0297 1.0000 Uiso RS . . . . .
C17 C 0.7156(2) 0.7500 -0.02614(18) 0.0226 1.0000 Uani S T . . . .
N18 N 0.80148(19) 0.7500 0.05570(16) 0.0316 1.0000 Uani S T . . . .
C19 C 0.7135(2) 0.7500 -0.30124(18) 0.0196 1.0000 Uani S T . . . .
C20 C 0.6894(2) 0.7500 -0.42745(18) 0.0216 1.0000 Uani S T . . . .
N21 N 0.6689(2) 0.7500 -0.52900(17) 0.0311 1.0000 Uani S T . . . .
C22 C 0.8519(2) 0.7500 -0.23959(18) 0.0214 1.0000 Uani S T . . . .
N23 N 0.96503(19) 0.7500 -0.19418(18) 0.0301 1.0000 Uani S T . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0165(7) 0.0283(8) 0.0158(7) 0.0000 0.0039(5) 0.0000
C2 0.0189(10) 0.0151(9) 0.0196(10) 0.0000 0.0039(8) 0.0000
C3 0.0199(10) 0.0186(10) 0.0179(10) 0.0000 0.0025(8) 0.0000
C4 0.0227(10) 0.0152(9) 0.0201(10) 0.0000 0.0052(8) 0.0000
C5 0.0166(9) 0.0231(10) 0.0191(10) 0.0000 0.0071(8) 0.0000
C6 0.0220(7) 0.0246(8) 0.0243(7) -0.0017(6) 0.0070(6) -0.0014(6)
C7 0.0289(12) 0.0241(11) 0.0204(10) 0.0000 0.0066(9) 0.0000
C8 0.0246(11) 0.0217(10) 0.0236(11) 0.0000 0.0029(9) 0.0000
C9 0.0321(12) 0.0172(10) 0.0223(10) 0.0000 0.0064(9) 0.0000
C10 0.0220(10) 0.0186(10) 0.0349(12) 0.0000 0.0135(9) 0.0000
C11 0.0203(10) 0.0218(10) 0.0238(11) 0.0000 0.0055(8) 0.0000
C12 0.0236(10) 0.0180(10) 0.0177(10) 0.0000 0.0085(8) 0.0000
O13 0.0179(7) 0.0356(9) 0.0154(7) 0.0000 0.0053(5) 0.0000
C14 0.0187(11) 0.0427(13) 0.0272(11) 0.0000 0.0099(9) 0.0000
C15 0.0244(11) 0.0252(11) 0.0202(10) 0.0000 0.0035(8) 0.0000
C16 0.0299(11) 0.0274(11) 0.0206(10) 0.0000 0.0036(9) 0.0000
C17 0.0231(11) 0.0241(11) 0.0216(10) 0.0000 0.0071(9) 0.0000
N18 0.0247(10) 0.0463(12) 0.0225(10) 0.0000 0.0011(8) 0.0000
C19 0.0191(10) 0.0183(10) 0.0216(10) 0.0000 0.0048(8) 0.0000
C20 0.0201(10) 0.0224(10) 0.0242(11) 0.0000 0.0090(8) 0.0000
N21 0.0328(11) 0.0368(11) 0.0270(11) 0.0000 0.0139(8) 0.0000
C22 0.0226(12) 0.0191(10) 0.0247(11) 0.0000 0.0096(9) 0.0000
N23 0.0205(10) 0.0325(11) 0.0374(11) 0.0000 0.0063(8) 0.0000

_refine_ls_extinction_coef       15.9(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          6.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.336(2) yes
O1 . C5 . 1.489(2) yes
C2 . C3 . 1.445(3) yes
C2 . C19 . 1.369(3) yes
C3 . C4 . 1.366(3) yes
C3 . C17 . 1.425(3) yes
C4 . C5 . 1.519(3) yes
C4 . C7 . 1.435(3) yes
C5 . C6 3_565 1.5202(18) yes
C5 . C6 . 1.5202(18) yes
C6 . H63 . 0.968 no
C6 . H62 . 0.974 no
C6 . H61 . 0.970 no
C7 . C8 . 1.344(3) yes
C7 . H71 . 0.976 no
C8 . C9 . 1.463(3) yes
C8 . H81 . 0.971 no
C9 . C10 . 1.414(3) yes
C9 . C16 . 1.382(3) yes
C10 . C11 . 1.385(3) yes
C10 . H101 . 0.947 no
C11 . C12 . 1.397(3) yes
C11 . H111 . 0.933 no
C12 . O13 . 1.365(2) yes
C12 . C15 . 1.397(3) yes
O13 . C14 . 1.428(2) yes
C14 . H142 3_565 0.972 no
C14 . H142 . 0.972 no
C14 . H143 . 0.980 no
C15 . C16 . 1.379(3) yes
C15 . H151 . 0.964 no
C16 . H161 . 0.962 no
C17 . N18 . 1.147(3) yes
C19 . C20 . 1.433(3) yes
C19 . C22 . 1.428(3) yes
C20 . N21 . 1.153(3) yes
C22 . N23 . 1.151(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C5 . 110.25(15) yes
O1 . C2 . C3 . 109.61(17) yes
O1 . C2 . C19 . 119.85(18) yes
C3 . C2 . C19 . 130.53(19) yes
C2 . C3 . C4 . 109.44(17) yes
C2 . C3 . C17 . 126.35(18) yes
C4 . C3 . C17 . 124.20(19) yes
C3 . C4 . C5 . 108.09(17) yes
C3 . C4 . C7 . 123.07(19) yes
C5 . C4 . C7 . 128.84(19) yes
C6 3_565 C5 . C4 . 114.09(10) yes
C6 3_565 C5 . O1 . 106.28(10) yes
C4 . C5 . O1 . 102.61(15) yes
C6 3_565 C5 . C6 . 112.34(16) yes
C4 . C5 . C6 . 114.09(10) yes
O1 . C5 . C6 . 106.28(10) yes
C5 . C6 . H63 . 110.6 no
C5 . C6 . H62 . 108.8 no
H63 . C6 . H62 . 109.1 no
C5 . C6 . H61 . 109.5 no
H63 . C6 . H61 . 108.6 no
H62 . C6 . H61 . 110.2 no
C4 . C7 . C8 . 126.0(2) yes
C4 . C7 . H71 . 118.8 no
C8 . C7 . H71 . 115.1 no
C7 . C8 . C9 . 126.0(2) yes
C7 . C8 . H81 . 115.8 no
C9 . C8 . H81 . 118.3 no
C8 . C9 . C10 . 124.1(2) yes
C8 . C9 . C16 . 117.8(2) yes
C10 . C9 . C16 . 118.0(2) yes
C9 . C10 . C11 . 121.3(2) yes
C9 . C10 . H101 . 122.1 no
C11 . C10 . H101 . 116.6 no
C10 . C11 . C12 . 119.21(19) yes
C10 . C11 . H111 . 122.6 no
C12 . C11 . H111 . 118.2 no
C11 . C12 . O13 . 116.24(17) yes
C11 . C12 . C15 . 119.95(19) yes
O13 . C12 . C15 . 123.81(19) yes
C12 . O13 . C14 . 117.58(16) yes
O13 . C14 . H142 3_565 109.6 no
O13 . C14 . H142 . 109.6 no
H142 3_565 C14 . H142 . 111.0 no
O13 . C14 . H143 . 107.7 no
H142 3_565 C14 . H143 . 109.4 no
H142 . C14 . H143 . 109.4 no
C12 . C15 . C16 . 119.9(2) yes
C12 . C15 . H151 . 120.1 no
C16 . C15 . H151 . 120.0 no
C9 . C16 . C15 . 121.6(2) yes
C9 . C16 . H161 . 119.4 no
C15 . C16 . H161 . 119.0 no
C3 . C17 . N18 . 175.2(2) yes
C2 . C19 . C20 . 119.46(19) yes
C2 . C19 . C22 . 123.05(19) yes
C20 . C19 . C22 . 117.49(18) yes
C19 . C20 . N21 . 179.5(2) yes
C19 . C22 . N23 . 177.3(2) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C16 . H161 . N18 1_455 124.40(7) 0.962 2.563 3.207(2) yes
C15 . H151 . N18 1_455 122.79(7) 0.964 2.585 3.211(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 29/05/12 at 14:27:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  63,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 29/05/12 at 14:27:26
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429527'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.0071(5)
_cell_length_b                   15.2572(8)
_cell_length_c                   14.9890(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.870(6)
_cell_angle_gamma                90
_cell_volume                     1785.14(19)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C19 H17 N3 O3 
# Dc =      1.25 Fooo =    728.00 Mu =      7.06 M =    335.36
# Found Formula = C20 H17 N3 O3 
# Dc =      1.29 FOOO =    728.00 Mu =      7.26 M =    347.37

_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_compound_source        ?
_chemical_formula_weight         347.37


_cell_measurement_reflns_used    9121
_cell_measurement_theta_min      4.1370
_cell_measurement_theta_max      66.9950
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.126
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_max          0.352

_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.726

# Sheldrick geometric approximatio 0.91 0.91 
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            19637
_reflns_number_total             3163
_diffrn_reflns_av_R_equivalents  0.066
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3163 
# Theoretical number of reflections is about 6393 


_diffrn_reflns_theta_min         4.189
_diffrn_reflns_theta_max         67.198
_diffrn_measured_fraction_theta_max 0.987

_diffrn_reflns_theta_full        67.198
_diffrn_measured_fraction_theta_full 0.987


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   3.01
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.22
_refine_diff_density_max         0.22


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3149
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0502
_refine_ls_wR_factor_ref         0.0858
_refine_ls_goodness_of_fit_ref   1.0087
_refine_ls_shift/su_max          0.0002781
_refine_ls_shift/su_mean         0.0000348


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3149
_refine_ls_R_factor_all          0.0502
_refine_ls_wR_factor_all         0.0858

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2835
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_gt          0.0800

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 843. 0.132E+04 653. 159. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.23766(15) 0.72348(8) 0.77085(8) 0.0350 1.0000 Uani . . . . . .
C2 C 0.2926(2) 0.69006(11) 0.85764(11) 0.0297 1.0000 Uani . . . . . .
C3 C 0.4506(2) 0.64675(12) 0.88136(12) 0.0309 1.0000 Uani . . . . . .
C4 C 0.5540(2) 0.64085(12) 0.81305(12) 0.0327 1.0000 Uani . . . . . .
C5 C 0.7005(2) 0.59472(11) 0.82033(12) 0.0325 1.0000 Uani . . . . . .
C6 C 0.8001(2) 0.59284(11) 0.75203(12) 0.0304 1.0000 Uani . . . . . .
C7 C 0.9484(2) 0.54689(11) 0.75840(12) 0.0296 1.0000 Uani . . . . . .
C8 C 1.0101(2) 0.56069(11) 0.67610(12) 0.0290 1.0000 Uani . . . . . .
O9 O 0.90504(15) 0.61513(8) 0.62083(8) 0.0331 1.0000 Uani . . . . . .
C10 C 0.7614(2) 0.64177(12) 0.66264(12) 0.0320 1.0000 Uani . . . . . .
C11 C 0.5994(2) 0.61208(15) 0.59585(13) 0.0435 1.0000 Uani . . . . . .
C12 C 0.7748(2) 0.74049(12) 0.67343(13) 0.0384 1.0000 Uani . . . . . .
C13 C 1.1485(2) 0.52808(11) 0.64750(12) 0.0315 1.0000 Uani . . . . . .
C14 C 1.1740(2) 0.55061(12) 0.55938(13) 0.0329 1.0000 Uani . . . . . .
N15 N 1.1958(2) 0.56848(11) 0.48808(12) 0.0427 1.0000 Uani . . . . . .
C16 C 1.2693(2) 0.46972(12) 0.70114(13) 0.0355 1.0000 Uani . . . . . .
N17 N 1.3699(2) 0.42243(12) 0.74126(13) 0.0506 1.0000 Uani . . . . . .
C18 C 1.0287(2) 0.49395(12) 0.83408(12) 0.0325 1.0000 Uani . . . . . .
N19 N 1.0868(2) 0.45146(11) 0.89636(12) 0.0442 1.0000 Uani . . . . . .
C20 C 0.5024(2) 0.61229(13) 0.96985(12) 0.0381 1.0000 Uani . . . . . .
C21 C 0.4000(3) 0.62106(14) 1.03149(13) 0.0426 1.0000 Uani . . . . . .
C22 C 0.2408(3) 0.66239(13) 1.00686(12) 0.0397 1.0000 Uani . . . . . .
C23 C 0.1864(2) 0.69630(12) 0.92023(12) 0.0325 1.0000 Uani . . . . . .
O24 O 0.03208(15) 0.73614(9) 0.88734(9) 0.0380 1.0000 Uani . . . . . .
C25 C -0.0729(3) 0.75115(15) 0.95168(14) 0.0455 1.0000 Uani . . . . . .
C26 C 0.2437(3) 0.81773(14) 0.76904(15) 0.0472 1.0000 Uani . . . . . .
H41 H 0.5115 0.6739 0.7575 0.0378 1.0000 Uiso R . . . . .
H51 H 0.7427 0.5604 0.8747 0.0381 1.0000 Uiso R . . . . .
H111 H 0.5979 0.6387 0.5356 0.0648 1.0000 Uiso R . . . . .
H112 H 0.5008 0.6340 0.6178 0.0644 1.0000 Uiso R . . . . .
H113 H 0.5929 0.5485 0.5914 0.0646 1.0000 Uiso R . . . . .
H121 H 0.7701 0.7661 0.6125 0.0572 1.0000 Uiso R . . . . .
H122 H 0.8858 0.7562 0.7144 0.0584 1.0000 Uiso R . . . . .
H123 H 0.6788 0.7628 0.6980 0.0577 1.0000 Uiso R . . . . .
H201 H 0.6119 0.5830 0.9877 0.0463 1.0000 Uiso R . . . . .
H211 H 0.4391 0.5989 1.0935 0.0510 1.0000 Uiso R . . . . .
H221 H 0.1677 0.6669 1.0506 0.0475 1.0000 Uiso R . . . . .
H251 H -0.1754 0.7827 0.9180 0.0676 1.0000 Uiso R . . . . .
H252 H -0.0107 0.7874 1.0023 0.0671 1.0000 Uiso R . . . . .
H253 H -0.1034 0.6948 0.9759 0.0667 1.0000 Uiso R . . . . .
H261 H 0.1915 0.8375 0.7087 0.0720 1.0000 Uiso R . . . . .
H262 H 0.1854 0.8428 0.8143 0.0714 1.0000 Uiso R . . . . .
H263 H 0.3641 0.8366 0.7831 0.0728 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0341(7) 0.0441(7) 0.0273(6) 0.0034(5) 0.0083(5) 0.0051(5)
C2 0.0317(9) 0.0319(9) 0.0261(8) -0.0018(7) 0.0079(7) -0.0030(7)
C3 0.0281(8) 0.0333(9) 0.0315(9) -0.0008(7) 0.0070(7) -0.0039(7)
C4 0.0299(9) 0.0341(9) 0.0349(9) 0.0007(7) 0.0090(7) -0.0009(7)
C5 0.0308(9) 0.0305(9) 0.0363(9) 0.0003(7) 0.0080(7) -0.0020(7)
C6 0.0279(8) 0.0277(9) 0.0351(9) -0.0029(7) 0.0060(7) -0.0034(7)
C7 0.0262(8) 0.0267(8) 0.0351(9) 0.0005(7) 0.0049(7) 0.0000(7)
C8 0.0252(8) 0.0263(8) 0.0346(9) -0.0017(7) 0.0049(7) 0.0001(7)
O9 0.0277(6) 0.0382(7) 0.0350(7) 0.0047(5) 0.0103(5) 0.0080(5)
C10 0.0239(8) 0.0388(10) 0.0342(9) -0.0006(7) 0.0086(7) 0.0053(7)
C11 0.0289(9) 0.0591(13) 0.0410(11) -0.0057(10) 0.0049(8) 0.0015(9)
C12 0.0397(10) 0.0348(10) 0.0421(11) 0.0082(8) 0.0123(8) 0.0088(8)
C13 0.0271(8) 0.0309(9) 0.0361(9) -0.0019(7) 0.0059(7) 0.0013(7)
C14 0.0246(9) 0.0353(10) 0.0392(10) -0.0037(8) 0.0081(7) 0.0019(7)
N15 0.0339(8) 0.0519(10) 0.0435(10) -0.0015(8) 0.0114(7) 0.0021(7)
C16 0.0311(9) 0.0337(10) 0.0431(10) -0.0005(8) 0.0113(8) 0.0007(8)
N17 0.0409(9) 0.0511(11) 0.0615(12) 0.0148(9) 0.0151(8) 0.0146(9)
C18 0.0295(9) 0.0304(9) 0.0383(10) 0.0007(8) 0.0092(8) -0.0012(7)
N19 0.0422(9) 0.0450(10) 0.0456(10) 0.0097(8) 0.0104(8) 0.0053(8)
C20 0.0352(10) 0.0395(10) 0.0389(10) 0.0049(8) 0.0070(8) -0.0005(8)
C21 0.0473(11) 0.0496(12) 0.0307(10) 0.0058(8) 0.0082(8) -0.0040(9)
C22 0.0455(11) 0.0461(11) 0.0309(9) -0.0011(8) 0.0159(8) -0.0057(9)
C23 0.0322(9) 0.0349(9) 0.0321(9) -0.0044(7) 0.0109(7) -0.0036(7)
O24 0.0307(7) 0.0498(8) 0.0376(7) -0.0042(6) 0.0160(5) 0.0019(6)
C25 0.0404(11) 0.0526(12) 0.0518(12) -0.0149(10) 0.0276(9) -0.0048(9)
C26 0.0491(12) 0.0464(12) 0.0481(12) 0.0145(9) 0.0153(9) 0.0022(9)

_refine_ls_extinction_coef       91(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.98(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.375(2) yes
O1 . C26 . 1.439(2) yes
C2 . C3 . 1.402(2) yes
C2 . C23 . 1.403(2) yes
C3 . C4 . 1.456(2) yes
C3 . C20 . 1.401(3) yes
C4 . C5 . 1.351(2) yes
C4 . H41 . 0.969 no
C5 . C6 . 1.431(2) yes
C5 . H51 . 0.965 no
C6 . C7 . 1.364(2) yes
C6 . C10 . 1.505(2) yes
C7 . C8 . 1.443(2) yes
C7 . C18 . 1.424(2) yes
C8 . O9 . 1.332(2) yes
C8 . C13 . 1.368(2) yes
O9 . C10 . 1.4838(19) yes
C10 . C11 . 1.520(2) yes
C10 . C12 . 1.516(3) yes
C11 . H111 . 0.988 no
C11 . H112 . 0.979 no
C11 . H113 . 0.972 no
C12 . H121 . 0.987 no
C12 . H122 . 0.991 no
C12 . H123 . 0.984 no
C13 . C14 . 1.423(3) yes
C13 . C16 . 1.424(2) yes
C14 . N15 . 1.153(2) yes
C16 . N17 . 1.147(2) yes
C18 . N19 . 1.147(2) yes
C20 . C21 . 1.372(3) yes
C20 . H201 . 0.967 no
C21 . C22 . 1.396(3) yes
C21 . H211 . 0.973 no
C22 . C23 . 1.375(3) yes
C22 . H221 . 0.974 no
C23 . O24 . 1.367(2) yes
O24 . C25 . 1.432(2) yes
C25 . H251 . 0.988 no
C25 . H252 . 0.981 no
C25 . H253 . 0.984 no
C26 . H261 . 0.957 no
C26 . H262 . 0.982 no
C26 . H263 . 0.983 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C26 . 112.55(14) yes
O1 . C2 . C3 . 119.68(15) yes
O1 . C2 . C23 . 119.59(15) yes
C3 . C2 . C23 . 120.67(16) yes
C2 . C3 . C4 . 118.27(16) yes
C2 . C3 . C20 . 118.50(16) yes
C4 . C3 . C20 . 123.22(16) yes
C3 . C4 . C5 . 126.49(17) yes
C3 . C4 . H41 . 115.3 no
C5 . C4 . H41 . 118.3 no
C4 . C5 . C6 . 124.37(17) yes
C4 . C5 . H51 . 119.1 no
C6 . C5 . H51 . 116.6 no
C5 . C6 . C7 . 125.13(16) yes
C5 . C6 . C10 . 126.16(15) yes
C7 . C6 . C10 . 108.70(15) yes
C6 . C7 . C8 . 108.91(15) yes
C6 . C7 . C18 . 125.39(16) yes
C8 . C7 . C18 . 125.70(15) yes
C7 . C8 . O9 . 109.47(14) yes
C7 . C8 . C13 . 132.12(16) yes
O9 . C8 . C13 . 118.40(15) yes
C8 . O9 . C10 . 110.48(13) yes
C6 . C10 . O9 . 102.42(13) yes
C6 . C10 . C11 . 114.49(15) yes
O9 . C10 . C11 . 105.57(14) yes
C6 . C10 . C12 . 113.72(15) yes
O9 . C10 . C12 . 105.91(14) yes
C11 . C10 . C12 . 113.32(16) yes
C10 . C11 . H111 . 108.3 no
C10 . C11 . H112 . 108.1 no
H111 . C11 . H112 . 108.7 no
C10 . C11 . H113 . 111.5 no
H111 . C11 . H113 . 111.0 no
H112 . C11 . H113 . 109.2 no
C10 . C12 . H121 . 107.9 no
C10 . C12 . H122 . 109.8 no
H121 . C12 . H122 . 108.8 no
C10 . C12 . H123 . 109.9 no
H121 . C12 . H123 . 109.7 no
H122 . C12 . H123 . 110.6 no
C8 . C13 . C14 . 119.79(16) yes
C8 . C13 . C16 . 123.10(16) yes
C14 . C13 . C16 . 117.09(15) yes
C13 . C14 . N15 . 179.49(18) yes
C13 . C16 . N17 . 177.1(2) yes
C7 . C18 . N19 . 176.99(19) yes
C3 . C20 . C21 . 120.38(18) yes
C3 . C20 . H201 . 119.6 no
C21 . C20 . H201 . 120.0 no
C20 . C21 . C22 . 120.91(18) yes
C20 . C21 . H211 . 119.7 no
C22 . C21 . H211 . 119.4 no
C21 . C22 . C23 . 119.88(17) yes
C21 . C22 . H221 . 120.3 no
C23 . C22 . H221 . 119.8 no
C2 . C23 . C22 . 119.62(17) yes
C2 . C23 . O24 . 115.02(15) yes
C22 . C23 . O24 . 125.36(16) yes
C23 . O24 . C25 . 116.59(15) yes
O24 . C25 . H251 . 106.2 no
O24 . C25 . H252 . 109.8 no
H251 . C25 . H252 . 110.0 no
O24 . C25 . H253 . 109.9 no
H251 . C25 . H253 . 111.6 no
H252 . C25 . H253 . 109.4 no
O1 . C26 . H261 . 108.9 no
O1 . C26 . H262 . 110.7 no
H261 . C26 . H262 . 110.9 no
O1 . C26 . H263 . 108.9 no
H261 . C26 . H263 . 108.1 no
H262 . C26 . H263 . 109.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C25 . H252 . O9 4_465 135.10(5) 0.981 2.521 3.290(3) yes
C26 . H263 . N17 3_756 156.12(6) 0.983 2.594 3.516(3) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 30/10/13 at 16:08:13
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 30/10/13 at 16:08:13
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429528'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   13.854(2)
_cell_length_b                   15.110(2)
_cell_length_c                   16.697(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3495.2(9)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C22 N1 O3 
# Dc =      1.24 Fooo =   1456.00 Mu =      7.01 M =    326.25
# Found Formula = C20 H17 N3 O3 
# Dc =      1.32 FOOO =   1456.00 Mu =      7.42 M =    347.37

_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_compound_source        ?
_chemical_formula_weight         347.37


_cell_measurement_reflns_used    4972
_cell_measurement_theta_min      4.9480
_cell_measurement_theta_max      66.9630
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.134
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_max          0.338

_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    0.742

# Sheldrick geometric approximatio 0.88 0.91 
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16513
_reflns_number_total             3110
_diffrn_reflns_av_R_equivalents  0.079
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3110 
# Theoretical number of reflections is about 6353 


_diffrn_reflns_theta_min         5.077
_diffrn_reflns_theta_max         67.889
_diffrn_measured_fraction_theta_max 0.980

_diffrn_reflns_theta_full        67.889
_diffrn_measured_fraction_theta_full 0.980


_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_reflns_limit_h_min              0
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   3.20
_oxford_diffrn_Wilson_scale      0.47

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.32


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0755
_refine_ls_wR_factor_ref         0.1105
_refine_ls_goodness_of_fit_ref   1.0253
_refine_ls_shift/su_max          0.0004325
_refine_ls_shift/su_mean         0.0000981


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3095
_refine_ls_R_factor_all          0.0755
_refine_ls_wR_factor_all         0.1105

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2377
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_gt          0.0947

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 494. 773. 367. 82.7 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.86765(13) 0.65499(11) 0.87586(11) 0.0468 1.0000 Uani . . . . . .
C2 C 0.87199(15) 0.57313(15) 0.90451(15) 0.0390 1.0000 Uani . . . . . .
C3 C 0.87504(15) 0.51121(16) 0.83977(14) 0.0385 1.0000 Uani . . . . . .
C4 C 0.87312(15) 0.55568(16) 0.76849(15) 0.0391 1.0000 Uani . . . . . .
C5 C 0.87033(17) 0.65414(15) 0.78701(14) 0.0407 1.0000 Uani . . . . . .
C6 C 0.96238(19) 0.70088(15) 0.76344(16) 0.0505 1.0000 Uani . . . . . .
H61 H 0.9645 0.7084 0.7050 0.0753 1.0000 Uiso R . . . . .
H62 H 1.0175 0.6672 0.7834 0.0746 1.0000 Uiso R . . . . .
H63 H 0.9618 0.7583 0.7892 0.0738 1.0000 Uiso R . . . . .
C7 C 0.77967(19) 0.70083(14) 0.75954(16) 0.0487 1.0000 Uani . . . . . .
H71 H 0.7832 0.7132 0.7020 0.0735 1.0000 Uiso R . . . . .
H72 H 0.7232 0.6651 0.7714 0.0725 1.0000 Uiso R . . . . .
H73 H 0.7767 0.7562 0.7898 0.0730 1.0000 Uiso R . . . . .
C8 C 0.87416(16) 0.51590(17) 0.69140(15) 0.0415 1.0000 Uani . . . . . .
C9 C 0.86983(16) 0.56215(16) 0.62199(16) 0.0424 1.0000 Uani . . . . . .
C10 C 0.87070(15) 0.53271(16) 0.54038(15) 0.0389 1.0000 Uani . . . . . .
C11 C 0.87793(15) 0.44405(16) 0.51398(16) 0.0392 1.0000 Uani . . . . . .
O12 O 0.88122(13) 0.38192(11) 0.57176(11) 0.0511 1.0000 Uani . . . . . .
C13 C 0.8882(2) 0.29104(17) 0.5490(2) 0.0627 1.0000 Uani . . . . . .
H131 H 0.8878 0.2559 0.5981 0.0930 1.0000 Uiso R . . . . .
H132 H 0.8345 0.2741 0.5142 0.0922 1.0000 Uiso R . . . . .
H133 H 0.9489 0.2815 0.5213 0.0920 1.0000 Uiso R . . . . .
C14 C 0.88074(17) 0.42509(17) 0.43287(16) 0.0419 1.0000 Uani . . . . . .
C15 C 0.87586(16) 0.49267(17) 0.37738(16) 0.0421 1.0000 Uani . . . . . .
O16 O 0.87913(13) 0.46669(12) 0.29921(11) 0.0523 1.0000 Uani . . . . . .
C17 C 0.87566(19) 0.53362(19) 0.23949(17) 0.0563 1.0000 Uani . . . . . .
H171 H 0.8787 0.5049 0.1874 0.0836 1.0000 Uiso R . . . . .
H173 H 0.8151 0.5667 0.2430 0.0836 1.0000 Uiso R . . . . .
H172 H 0.9298 0.5735 0.2451 0.0835 1.0000 Uiso R . . . . .
C18 C 0.86771(17) 0.58012(17) 0.40090(16) 0.0462 1.0000 Uani . . . . . .
C19 C 0.86510(18) 0.59806(16) 0.48172(16) 0.0461 1.0000 Uani . . . . . .
H191 H 0.8584 0.6566 0.4973 0.0552 1.0000 Uiso R . . . . .
H181 H 0.8626 0.6268 0.3636 0.0550 1.0000 Uiso R . . . . .
H141 H 0.8866 0.3671 0.4166 0.0494 1.0000 Uiso R . . . . .
H91 H 0.8665 0.6239 0.6280 0.0501 1.0000 Uiso R . . . . .
H81 H 0.8777 0.4543 0.6893 0.0495 1.0000 Uiso R . . . . .
C20 C 0.88089(17) 0.41746(16) 0.84834(16) 0.0428 1.0000 Uani . . . . . .
N21 N 0.88599(18) 0.34196(14) 0.85163(17) 0.0612 1.0000 Uani . . . . . .
C22 C 0.87215(16) 0.56133(15) 0.98566(16) 0.0405 1.0000 Uani . . . . . .
C23 C 0.87942(17) 0.47612(16) 1.02250(16) 0.0425 1.0000 Uani . . . . . .
N24 N 0.8857(2) 0.41155(16) 1.05626(16) 0.0618 1.0000 Uani . . . . . .
C25 C 0.86951(18) 0.63554(18) 1.03846(16) 0.0467 1.0000 Uani . . . . . .
N26 N 0.86775(19) 0.69494(15) 1.08071(16) 0.0650 1.0000 Uani . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0748(12) 0.0279(9) 0.0377(9) -0.0015(7) 0.0027(7) 0.0023(7)
C2 0.0438(11) 0.0299(12) 0.0432(13) 0.0030(10) 0.0010(9) -0.0009(8)
C3 0.0486(13) 0.0297(11) 0.0373(13) 0.0004(10) 0.0029(9) -0.0012(9)
C4 0.0443(12) 0.0309(12) 0.0421(14) -0.0027(10) 0.0016(9) 0.0004(8)
C5 0.0617(14) 0.0294(12) 0.0309(12) -0.0019(9) 0.0034(9) 0.0010(9)
C6 0.0602(15) 0.0367(13) 0.0546(15) -0.0027(11) 0.0040(12) -0.0065(10)
C7 0.0624(16) 0.0343(12) 0.0492(14) 0.0020(11) 0.0037(11) 0.0074(10)
C8 0.0511(13) 0.0308(12) 0.0426(14) -0.0038(10) 0.0016(9) 0.0002(9)
C9 0.0537(13) 0.0293(13) 0.0443(14) -0.0033(9) -0.0012(10) -0.0017(9)
C10 0.0441(12) 0.0317(13) 0.0411(13) -0.0043(10) 0.0007(9) -0.0024(9)
C11 0.0436(11) 0.0325(13) 0.0416(13) -0.0033(10) -0.0007(10) 0.0002(8)
O12 0.0795(13) 0.0265(9) 0.0475(11) 0.0014(7) -0.0023(8) 0.0014(7)
C13 0.093(2) 0.0263(13) 0.0692(19) -0.0027(12) -0.0055(15) 0.0033(12)
C14 0.0488(13) 0.0319(12) 0.0452(14) -0.0057(11) -0.0021(10) 0.0003(9)
C15 0.0461(13) 0.0403(13) 0.0400(13) -0.0056(11) -0.0020(9) -0.0022(9)
O16 0.0737(12) 0.0445(11) 0.0388(10) -0.0091(8) 0.0012(8) -0.0006(8)
C17 0.078(2) 0.0504(17) 0.0406(15) 0.0029(12) 0.0041(12) -0.0006(11)
C18 0.0575(14) 0.0338(13) 0.0474(15) 0.0027(11) 0.0009(11) -0.0007(10)
C19 0.0608(14) 0.0294(13) 0.0479(15) -0.0047(11) 0.0002(11) 0.0001(10)
C20 0.0514(13) 0.0324(13) 0.0446(14) 0.0005(11) -0.0022(10) 0.0005(9)
N21 0.0832(17) 0.0286(12) 0.0718(17) -0.0059(11) -0.0028(12) 0.0022(9)
C22 0.0511(13) 0.0301(13) 0.0403(13) 0.0000(9) -0.0001(10) 0.0011(9)
C23 0.0541(14) 0.0319(13) 0.0414(13) -0.0019(10) 0.0009(10) -0.0005(9)
N24 0.0896(18) 0.0333(13) 0.0626(15) 0.0048(11) -0.0050(12) 0.0012(11)
C25 0.0635(15) 0.0333(13) 0.0434(14) 0.0040(11) -0.0022(10) 0.0023(10)
N26 0.106(2) 0.0361(13) 0.0525(14) -0.0077(11) -0.0011(13) 0.0058(11)

_refine_ls_extinction_coef       33.4(6)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          1.564(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.328(3) yes
O1 . C5 . 1.484(3) yes
C2 . C3 . 1.430(3) yes
C2 . C22 . 1.367(3) yes
C3 . C4 . 1.367(3) yes
C3 . C20 . 1.426(3) yes
C4 . C5 . 1.520(3) yes
C4 . C8 . 1.421(3) yes
C5 . C6 . 1.510(3) yes
C5 . C7 . 1.512(3) yes
C6 . H61 . 0.984 no
C6 . H62 . 0.976 no
C6 . H63 . 0.969 no
C7 . H71 . 0.981 no
C7 . H72 . 0.971 no
C7 . H73 . 0.977 no
C8 . C9 . 1.355(4) yes
C8 . H81 . 0.932 no
C9 . C10 . 1.433(3) yes
C9 . H91 . 0.940 no
C10 . C11 . 1.414(3) yes
C10 . C19 . 1.393(3) yes
C11 . O12 . 1.347(3) yes
C11 . C14 . 1.385(4) yes
O12 . C13 . 1.428(3) yes
C13 . H131 . 0.976 no
C13 . H132 . 0.978 no
C13 . H133 . 0.970 no
C14 . C15 . 1.380(4) yes
C14 . H141 . 0.921 no
C15 . O16 . 1.364(3) yes
C15 . C18 . 1.383(4) yes
O16 . C17 . 1.421(3) yes
C17 . H171 . 0.973 no
C17 . H173 . 0.978 no
C17 . H172 . 0.966 no
C18 . C19 . 1.377(4) yes
C18 . H181 . 0.943 no
C19 . H191 . 0.927 no
C20 . N21 . 1.144(3) yes
C22 . C23 . 1.430(3) yes
C22 . C25 . 1.427(3) yes
C23 . N24 . 1.130(3) yes
C25 . N26 . 1.142(4) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C5 . 110.55(18) yes
O1 . C2 . C3 . 109.8(2) yes
O1 . C2 . C22 . 118.6(2) yes
C3 . C2 . C22 . 131.6(2) yes
C2 . C3 . C4 . 109.6(2) yes
C2 . C3 . C20 . 125.1(2) yes
C4 . C3 . C20 . 125.2(2) yes
C3 . C4 . C5 . 107.7(2) yes
C3 . C4 . C8 . 125.5(2) yes
C5 . C4 . C8 . 126.8(2) yes
C4 . C5 . O1 . 102.27(19) yes
C4 . C5 . C6 . 112.53(19) yes
O1 . C5 . C6 . 106.1(2) yes
C4 . C5 . C7 . 114.6(2) yes
O1 . C5 . C7 . 106.17(19) yes
C6 . C5 . C7 . 113.9(2) yes
C5 . C6 . H61 . 109.7 no
C5 . C6 . H62 . 109.2 no
H61 . C6 . H62 . 112.0 no
C5 . C6 . H63 . 107.2 no
H61 . C6 . H63 . 109.8 no
H62 . C6 . H63 . 108.7 no
C5 . C7 . H71 . 110.2 no
C5 . C7 . H72 . 110.4 no
H71 . C7 . H72 . 110.3 no
C5 . C7 . H73 . 106.1 no
H71 . C7 . H73 . 110.2 no
H72 . C7 . H73 . 109.7 no
C4 . C8 . C9 . 123.8(2) yes
C4 . C8 . H81 . 117.1 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 130.8(2) yes
C8 . C9 . H91 . 115.0 no
C10 . C9 . H91 . 114.2 no
C9 . C10 . C11 . 126.2(2) yes
C9 . C10 . C19 . 116.6(2) yes
C11 . C10 . C19 . 117.2(2) yes
C10 . C11 . O12 . 116.1(2) yes
C10 . C11 . C14 . 120.2(2) yes
O12 . C11 . C14 . 123.7(2) yes
C11 . O12 . C13 . 118.8(2) yes
O12 . C13 . H131 . 107.4 no
O12 . C13 . H132 . 111.0 no
H131 . C13 . H132 . 110.6 no
O12 . C13 . H133 . 109.2 no
H131 . C13 . H133 . 108.9 no
H132 . C13 . H133 . 109.7 no
C11 . C14 . C15 . 120.1(2) yes
C11 . C14 . H141 . 119.2 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . O16 . 115.3(2) yes
C14 . C15 . C18 . 121.3(2) yes
O16 . C15 . C18 . 123.3(3) yes
C15 . O16 . C17 . 117.7(2) yes
O16 . C17 . H171 . 107.9 no
O16 . C17 . H173 . 110.5 no
H171 . C17 . H173 . 108.6 no
O16 . C17 . H172 . 110.5 no
H171 . C17 . H172 . 109.4 no
H173 . C17 . H172 . 109.9 no
C15 . C18 . C19 . 117.9(2) yes
C15 . C18 . H181 . 122.2 no
C19 . C18 . H181 . 119.9 no
C10 . C19 . C18 . 123.2(2) yes
C10 . C19 . H191 . 119.0 no
C18 . C19 . H191 . 117.7 no
C3 . C20 . N21 . 177.0(3) yes
C2 . C22 . C23 . 122.9(2) yes
C2 . C22 . C25 . 120.7(2) yes
C23 . C22 . C25 . 116.3(2) yes
C22 . C23 . N24 . 175.5(3) yes
C22 . C25 . N26 . 179.8(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C7 . H72 . O16 5_665 160.40(7) 0.971 2.489 3.418(4) yes
C8 . H81 . O12 . 121.00 0.932 2.248 2.846(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 13/11/13 at 09:54:14
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   6,X'S) H   (  61,X'S) H   (  62,X'S) H   (  63,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) H   (  73,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 173,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 13/11/13 at 09:54:14
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429529'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   10.397(2)
_cell_length_b                   9.8280(10)
_cell_length_c                   17.179(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.990(10)
_cell_angle_gamma                90
_cell_volume                     1748.7(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C22 H20 N2 O2 
# Dc =      1.31 Fooo =    728.00 Mu =      6.74 M =    344.41
# Found Formula = C20 H17 N3 O3 
# Dc =      1.32 FOOO =    728.00 Mu =      7.41 M =    347.37

_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_compound_source        ?
_chemical_formula_weight         347.37


_cell_measurement_reflns_used    4290
_cell_measurement_theta_min      4.1730
_cell_measurement_theta_max      66.8020
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.084
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_max          0.456

_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.741

# Sheldrick geometric approximatio 0.91 0.94 
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13075
_reflns_number_total             3103
_diffrn_reflns_av_R_equivalents  0.091
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3103 
# Theoretical number of reflections is about 6353 


_diffrn_reflns_theta_min         4.268
_diffrn_reflns_theta_max         67.856
_diffrn_measured_fraction_theta_max 0.975

_diffrn_reflns_theta_full        67.676
_diffrn_measured_fraction_theta_full 0.979


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   3.46
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.42
_refine_diff_density_max         0.33


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0837
_refine_ls_wR_factor_ref         0.2043
_refine_ls_goodness_of_fit_ref   0.9987
_refine_ls_shift/su_max          0.0001793
_refine_ls_shift/su_mean         0.0000250


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3091
_refine_ls_R_factor_all          0.0837
_refine_ls_wR_factor_all         0.2043

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2401
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_gt          0.1605

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.274E+04 0.457E+04 0.276E+04 0.109E+04 220. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.40874(19) 0.2726(2) 0.33411(10) 0.0397 1.0000 Uani . . . . . .
C2 C 0.3831(2) 0.3286(3) 0.40173(15) 0.0353 1.0000 Uani . . . . . .
C3 C 0.4652(3) 0.2702(3) 0.46434(15) 0.0354 1.0000 Uani . . . . . .
C4 C 0.4664(3) 0.3022(3) 0.54541(16) 0.0392 1.0000 Uani . . . . . .
N5 N 0.4730(3) 0.3244(3) 0.61074(15) 0.0567 1.0000 Uani . . . . . .
C6 C 0.5468(3) 0.1784(3) 0.43435(15) 0.0358 1.0000 Uani . . . . . .
C7 C 0.5190(3) 0.1779(3) 0.34648(15) 0.0361 1.0000 Uani . . . . . .
C8 C 0.6285(3) 0.2406(3) 0.30571(16) 0.0406 1.0000 Uani . . . . . .
H81 H 0.7025 0.1813 0.3099 0.0617 1.0000 Uiso R . . . . .
H82 H 0.6011 0.2521 0.2502 0.0614 1.0000 Uiso R . . . . .
H83 H 0.6520 0.3284 0.3284 0.0619 1.0000 Uiso R . . . . .
C9 C 0.4721(3) 0.0431(3) 0.31137(16) 0.0423 1.0000 Uani . . . . . .
H91 H 0.5428 -0.0220 0.3153 0.0634 1.0000 Uiso R . . . . .
H92 H 0.4408 0.0573 0.2577 0.0636 1.0000 Uiso R . . . . .
H93 H 0.4024 0.0092 0.3405 0.0634 1.0000 Uiso R . . . . .
C10 C 0.6437(3) 0.1047(3) 0.48061(16) 0.0391 1.0000 Uani . . . . . .
C11 C 0.7215(3) 0.0094(3) 0.45265(16) 0.0382 1.0000 Uani . . . . . .
C12 C 0.8197(3) -0.0723(3) 0.49546(15) 0.0363 1.0000 Uani . . . . . .
C13 C 0.8688(3) -0.0509(3) 0.57333(16) 0.0382 1.0000 Uani . . . . . .
O14 O 0.81975(19) 0.0586(2) 0.60975(11) 0.0430 1.0000 Uani . . . . . .
C15 C 0.8727(3) 0.0923(3) 0.68625(17) 0.0470 1.0000 Uani . . . . . .
H151 H 0.8341 0.1776 0.7006 0.0717 1.0000 Uiso R . . . . .
H152 H 0.8519 0.0213 0.7217 0.0719 1.0000 Uiso R . . . . .
H153 H 0.9653 0.1005 0.6859 0.0719 1.0000 Uiso R . . . . .
C16 C 0.9631(3) -0.1351(3) 0.60964(18) 0.0450 1.0000 Uani . . . . . .
C17 C 1.0090(3) -0.2422(3) 0.56766(19) 0.0481 1.0000 Uani . . . . . .
C18 C 0.9645(3) -0.2667(3) 0.49104(19) 0.0456 1.0000 Uani . . . . . .
C19 C 0.8712(3) -0.1827(3) 0.45486(17) 0.0414 1.0000 Uani . . . . . .
O20 O 0.8222(2) -0.1962(2) 0.37906(12) 0.0494 1.0000 Uani . . . . . .
C21 C 0.8514(4) -0.3152(3) 0.33745(19) 0.0545 1.0000 Uani . . . . . .
H212 H 0.8066 -0.3100 0.2852 0.0815 1.0000 Uiso R . . . . .
H213 H 0.8218 -0.3956 0.3646 0.0813 1.0000 Uiso R . . . . .
H211 H 0.9439 -0.3213 0.3346 0.0819 1.0000 Uiso R . . . . .
H181 H 0.9975 -0.3394 0.4640 0.0560 1.0000 Uiso R . . . . .
H171 H 1.0723 -0.3000 0.5924 0.0573 1.0000 Uiso R . . . . .
H161 H 0.9954 -0.1180 0.6614 0.0542 1.0000 Uiso R . . . . .
H111 H 0.7101 -0.0055 0.3981 0.0469 1.0000 Uiso R . . . . .
H101 H 0.6512 0.1251 0.5340 0.0467 1.0000 Uiso R . . . . .
C22 C 0.2916(3) 0.4276(3) 0.40347(15) 0.0375 1.0000 Uani . . . . . .
C23 C 0.2196(3) 0.4732(3) 0.33414(17) 0.0410 1.0000 Uani . . . . . .
N24 N 0.1599(3) 0.5140(3) 0.28017(17) 0.0559 1.0000 Uani . . . . . .
C25 C 0.2687(3) 0.4955(3) 0.47377(17) 0.0402 1.0000 Uani . . . . . .
N26 N 0.2507(3) 0.5549(3) 0.52974(16) 0.0515 1.0000 Uani . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0431(11) 0.0470(11) 0.0293(10) -0.0012(7) 0.0047(8) 0.0080(8)
C2 0.0350(13) 0.0372(14) 0.0344(13) -0.0016(10) 0.0074(10) 0.0002(10)
C3 0.0381(14) 0.0376(14) 0.0312(13) 0.0007(10) 0.0067(10) 0.0016(10)
C4 0.0416(15) 0.0437(14) 0.0331(15) 0.0010(11) 0.0077(11) 0.0078(11)
N5 0.0651(18) 0.0698(19) 0.0356(14) -0.0024(12) 0.0069(12) 0.0121(14)
C6 0.0384(14) 0.0370(14) 0.0327(13) 0.0026(10) 0.0073(10) 0.0028(11)
C7 0.0391(14) 0.0386(14) 0.0315(13) -0.0019(10) 0.0077(10) 0.0061(11)
C8 0.0415(15) 0.0447(16) 0.0364(14) 0.0024(11) 0.0083(11) 0.0006(11)
C9 0.0447(15) 0.0421(15) 0.0400(15) -0.0002(12) 0.0033(12) -0.0024(12)
C10 0.0387(14) 0.0443(16) 0.0349(14) 0.0041(11) 0.0071(11) 0.0050(11)
C11 0.0395(14) 0.0385(14) 0.0375(13) 0.0031(11) 0.0081(11) 0.0034(11)
C12 0.0340(13) 0.0378(14) 0.0385(14) 0.0007(11) 0.0112(11) 0.0006(10)
C13 0.0381(13) 0.0357(13) 0.0421(14) 0.0027(11) 0.0104(11) 0.0033(11)
O14 0.0430(11) 0.0482(12) 0.0383(10) -0.0019(8) 0.0056(8) 0.0100(8)
C15 0.0458(16) 0.0500(17) 0.0451(16) -0.0021(13) 0.0035(12) 0.0027(13)
C16 0.0424(15) 0.0437(16) 0.0488(16) 0.0025(12) 0.0040(12) 0.0030(12)
C17 0.0425(16) 0.0438(16) 0.0581(19) 0.0033(13) 0.0042(13) 0.0071(12)
C18 0.0439(16) 0.0378(15) 0.0565(18) -0.0010(13) 0.0114(13) 0.0062(12)
C19 0.0415(15) 0.0389(15) 0.0450(15) 0.0005(11) 0.0109(12) 0.0021(11)
O20 0.0584(13) 0.0479(12) 0.0429(11) -0.0046(9) 0.0091(9) 0.0130(10)
C21 0.069(2) 0.0453(18) 0.0514(18) -0.0087(14) 0.0175(15) 0.0067(15)
C22 0.0373(14) 0.0380(14) 0.0376(14) 0.0000(11) 0.0051(11) 0.0017(11)
C23 0.0399(14) 0.0397(15) 0.0436(15) 0.0007(12) 0.0047(12) 0.0030(11)
N24 0.0561(16) 0.0570(17) 0.0533(16) 0.0041(13) -0.0031(13) 0.0061(13)
C25 0.0369(14) 0.0388(15) 0.0456(16) 0.0011(12) 0.0069(11) 0.0057(11)
N26 0.0535(15) 0.0480(15) 0.0542(16) -0.0062(12) 0.0111(12) 0.0080(12)

_refine_ls_extinction_coef       36(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          5.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.333(3) yes
O1 . C7 . 1.477(3) yes
C2 . C3 . 1.434(4) yes
C2 . C22 . 1.362(4) yes
C3 . C4 . 1.427(4) yes
C3 . C6 . 1.370(4) yes
C4 . N5 . 1.139(4) yes
C6 . C7 . 1.512(4) yes
C6 . C10 . 1.426(4) yes
C7 . C8 . 1.518(4) yes
C7 . C9 . 1.518(4) yes
C8 . H81 . 0.963 no
C8 . H82 . 0.978 no
C8 . H83 . 0.970 no
C9 . H91 . 0.972 no
C9 . H92 . 0.961 no
C9 . H93 . 0.975 no
C10 . C11 . 1.352(4) yes
C10 . H101 . 0.936 no
C11 . C12 . 1.448(4) yes
C11 . H111 . 0.946 no
C12 . C13 . 1.406(4) yes
C12 . C19 . 1.419(4) yes
C13 . O14 . 1.365(3) yes
C13 . C16 . 1.389(4) yes
O14 . C15 . 1.419(3) yes
C15 . H151 . 0.971 no
C15 . H152 . 0.963 no
C15 . H153 . 0.966 no
C16 . C17 . 1.384(4) yes
C16 . H161 . 0.939 no
C17 . C18 . 1.378(5) yes
C17 . H171 . 0.943 no
C18 . C19 . 1.380(4) yes
C18 . H181 . 0.934 no
C19 . O20 . 1.363(4) yes
O20 . C21 . 1.418(4) yes
C21 . H212 . 0.976 no
C21 . H213 . 0.980 no
C21 . H211 . 0.969 no
C22 . C23 . 1.423(4) yes
C22 . C25 . 1.418(4) yes
C23 . N24 . 1.142(4) yes
C25 . N26 . 1.154(4) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C7 . 110.28(19) yes
O1 . C2 . C3 . 109.7(2) yes
O1 . C2 . C22 . 120.5(2) yes
C3 . C2 . C22 . 129.9(2) yes
C2 . C3 . C4 . 126.7(2) yes
C2 . C3 . C6 . 109.2(2) yes
C4 . C3 . C6 . 124.0(3) yes
C3 . C4 . N5 . 176.6(3) yes
C3 . C6 . C7 . 107.9(2) yes
C3 . C6 . C10 . 123.8(2) yes
C7 . C6 . C10 . 128.3(2) yes
C6 . C7 . O1 . 102.71(19) yes
C6 . C7 . C8 . 111.9(2) yes
O1 . C7 . C8 . 106.3(2) yes
C6 . C7 . C9 . 115.3(2) yes
O1 . C7 . C9 . 105.9(2) yes
C8 . C7 . C9 . 113.5(2) yes
C7 . C8 . H81 . 110.3 no
C7 . C8 . H82 . 109.3 no
H81 . C8 . H82 . 107.8 no
C7 . C8 . H83 . 110.4 no
H81 . C8 . H83 . 109.7 no
H82 . C8 . H83 . 109.4 no
C7 . C9 . H91 . 109.4 no
C7 . C9 . H92 . 109.0 no
H91 . C9 . H92 . 110.7 no
C7 . C9 . H93 . 108.7 no
H91 . C9 . H93 . 109.3 no
H92 . C9 . H93 . 109.7 no
C6 . C10 . C11 . 124.7(3) yes
C6 . C10 . H101 . 115.6 no
C11 . C10 . H101 . 119.7 no
C10 . C11 . C12 . 128.3(3) yes
C10 . C11 . H111 . 115.6 no
C12 . C11 . H111 . 116.1 no
C11 . C12 . C13 . 125.6(2) yes
C11 . C12 . C19 . 117.0(3) yes
C13 . C12 . C19 . 117.4(3) yes
C12 . C13 . O14 . 115.8(2) yes
C12 . C13 . C16 . 121.5(3) yes
O14 . C13 . C16 . 122.7(3) yes
C13 . O14 . C15 . 118.6(2) yes
O14 . C15 . H151 . 107.6 no
O14 . C15 . H152 . 109.1 no
H151 . C15 . H152 . 110.1 no
O14 . C15 . H153 . 108.6 no
H151 . C15 . H153 . 111.3 no
H152 . C15 . H153 . 110.1 no
C13 . C16 . C17 . 118.7(3) yes
C13 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 121.3 no
C16 . C17 . C18 . 121.9(3) yes
C16 . C17 . H171 . 118.9 no
C18 . C17 . H171 . 119.2 no
C17 . C18 . C19 . 119.4(3) yes
C17 . C18 . H181 . 120.1 no
C19 . C18 . H181 . 120.6 no
C12 . C19 . C18 . 121.1(3) yes
C12 . C19 . O20 . 114.7(3) yes
C18 . C19 . O20 . 124.2(3) yes
C19 . O20 . C21 . 118.9(3) yes
O20 . C21 . H212 . 108.3 no
O20 . C21 . H213 . 109.6 no
H212 . C21 . H213 . 109.6 no
O20 . C21 . H211 . 109.5 no
H212 . C21 . H211 . 110.7 no
H213 . C21 . H211 . 109.1 no
C2 . C22 . C23 . 121.6(2) yes
C2 . C22 . C25 . 121.6(2) yes
C23 . C22 . C25 . 116.7(2) yes
C22 . C23 . N24 . 177.3(3) yes
C22 . C25 . N26 . 177.7(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C21 . H213 . N26 2_656 162.55(9) 0.980 2.560 3.507(4) yes
C10 . H101 . O14 . 121.00 0.936 2.190 2.787(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/11/13 at 14:37:36
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) H   (  83,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  21,X'S) H   ( 212,X'S) H   ( 213,X'S) H   ( 211,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/11/13 at 14:37:36
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429530'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   15.229(2)
_cell_length_b                   7.5088(7)
_cell_length_c                   16.6390(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.397(7)
_cell_angle_gamma                90
_cell_volume                     1901.0(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C24 H24 N3 O2 
# Dc =      1.35 Fooo =    792.00 Mu =      6.94 M =    386.47
# Found Formula = C21 H19 N3 O4 
# Dc =      1.32 FOOO =    792.00 Mu =      7.65 M =    377.40

_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_compound_source        ?
_chemical_formula_weight         377.40


_cell_measurement_reflns_used    7073
_cell_measurement_theta_min      2.7900
_cell_measurement_theta_max      66.8750
_cell_measurement_temperature    150

_exptl_crystal_description       neddle
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.048
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_max          0.351

_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.765

# Sheldrick geometric approximatio 0.96 0.96 
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_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_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            17984
_reflns_number_total             3353
_diffrn_reflns_av_R_equivalents  0.098
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3353 
# Theoretical number of reflections is about 6785 


_diffrn_reflns_theta_min         3.855
_diffrn_reflns_theta_max         67.047
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        67.047
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -18
_reflns_limit_h_max              18
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   2.86
_oxford_diffrn_Wilson_scale      0.03

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.35
_refine_diff_density_max         0.34


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         3336
_refine_ls_number_restraints     0
_refine_ls_number_parameters     253
_oxford_refine_ls_R_factor_ref   0.0762
_refine_ls_wR_factor_ref         0.1412
_refine_ls_goodness_of_fit_ref   1.0740
_refine_ls_shift/su_max          0.0004823
_refine_ls_shift/su_mean         0.0001084


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3336
_refine_ls_R_factor_all          0.0762
_refine_ls_wR_factor_all         0.1412

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2852
_refine_ls_R_factor_gt           0.0693
_refine_ls_wR_factor_gt          0.1247

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.148E+04 0.232E+04 0.118E+04 291. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.30660(12) 0.4110(2) 0.64675(10) 0.0301 1.0000 Uani . . . . . .
C2 C 0.31177(17) 0.3927(3) 0.55850(14) 0.0268 1.0000 Uani . . . . . .
C3 C 0.36950(16) 0.5468(3) 0.53720(14) 0.0244 1.0000 Uani . . . . . .
C4 C 0.39588(16) 0.5917(3) 0.45827(14) 0.0253 1.0000 Uani . . . . . .
C5 C 0.37436(16) 0.4969(3) 0.39093(14) 0.0256 1.0000 Uani . . . . . .
C6 C 0.39863(16) 0.5357(3) 0.31002(13) 0.0237 1.0000 Uani . . . . . .
C7 C 0.37042(17) 0.4173(3) 0.24772(14) 0.0247 1.0000 Uani . . . . . .
O8 O 0.31858(12) 0.2778(2) 0.26766(11) 0.0307 1.0000 Uani . . . . . .
C9 C 0.34181(19) 0.1043(3) 0.23983(17) 0.0357 1.0000 Uani . . . . . .
H91 H 0.3231 0.0158 0.2782 0.0540 1.0000 Uiso R . . . . .
H92 H 0.4048 0.0956 0.2362 0.0545 1.0000 Uiso R . . . . .
H93 H 0.3126 0.0785 0.1880 0.0545 1.0000 Uiso R . . . . .
C10 C 0.39147(17) 0.4513(3) 0.16909(14) 0.0265 1.0000 Uani . . . . . .
O11 O 0.36194(13) 0.3381(3) 0.10819(10) 0.0344 1.0000 Uani . . . . . .
C12 C 0.2898(2) 0.4061(5) 0.06306(19) 0.0497 1.0000 Uani . . . . . .
H122 H 0.2776 0.3267 0.0174 0.0740 1.0000 Uiso R . . . . .
H121 H 0.3009 0.5256 0.0454 0.0743 1.0000 Uiso R . . . . .
H123 H 0.2394 0.4044 0.0968 0.0743 1.0000 Uiso R . . . . .
C13 C 0.44246(18) 0.5996(3) 0.15118(14) 0.0269 1.0000 Uani . . . . . .
O14 O 0.45947(14) 0.6181(3) 0.07216(10) 0.0383 1.0000 Uani . . . . . .
C15 C 0.5093(2) 0.7686(4) 0.04955(17) 0.0418 1.0000 Uani . . . . . .
H152 H 0.5135 0.7664 -0.0084 0.0631 1.0000 Uiso R . . . . .
H153 H 0.5682 0.7642 0.0743 0.0625 1.0000 Uiso R . . . . .
H151 H 0.4790 0.8777 0.0635 0.0623 1.0000 Uiso R . . . . .
C16 C 0.46971(16) 0.7168(3) 0.21170(15) 0.0287 1.0000 Uani . . . . . .
C17 C 0.44715(16) 0.6853(3) 0.28934(14) 0.0267 1.0000 Uani . . . . . .
H171 H 0.4640 0.7682 0.3297 0.0320 1.0000 Uiso R . . . . .
H161 H 0.5029 0.8189 0.1997 0.0344 1.0000 Uiso R . . . . .
H51 H 0.3412 0.3899 0.3980 0.0299 1.0000 Uiso R . . . . .
H41 H 0.4302 0.6963 0.4527 0.0309 1.0000 Uiso R . . . . .
C18 C 0.39216(16) 0.6379(3) 0.60602(14) 0.0256 1.0000 Uani . . . . . .
C19 C 0.35205(16) 0.5526(3) 0.67241(14) 0.0256 1.0000 Uani . . . . . .
C20 C 0.35499(17) 0.5925(3) 0.75303(14) 0.0274 1.0000 Uani . . . . . .
C21 C 0.39821(18) 0.7460(4) 0.78518(15) 0.0324 1.0000 Uani . . . . . .
N22 N 0.43067(18) 0.8697(4) 0.81387(15) 0.0484 1.0000 Uani . . . . . .
C23 C 0.31233(18) 0.4794(4) 0.80728(14) 0.0321 1.0000 Uani . . . . . .
N24 N 0.27918(19) 0.3871(4) 0.85153(14) 0.0466 1.0000 Uani . . . . . .
C25 C 0.44902(17) 0.7874(3) 0.60978(14) 0.0276 1.0000 Uani . . . . . .
N26 N 0.49689(17) 0.9054(3) 0.60885(14) 0.0387 1.0000 Uani . . . . . .
C27 C 0.35257(18) 0.2123(4) 0.54561(15) 0.0312 1.0000 Uani . . . . . .
H271 H 0.3562 0.1888 0.4890 0.0471 1.0000 Uiso R . . . . .
H273 H 0.4105 0.2098 0.5707 0.0463 1.0000 Uiso R . . . . .
H272 H 0.3199 0.1179 0.5696 0.0465 1.0000 Uiso R . . . . .
C28 C 0.21762(18) 0.4083(4) 0.52472(16) 0.0351 1.0000 Uani . . . . . .
H282 H 0.2152 0.3968 0.4675 0.0527 1.0000 Uiso R . . . . .
H281 H 0.1821 0.3155 0.5463 0.0528 1.0000 Uiso R . . . . .
H283 H 0.1951 0.5202 0.5384 0.0519 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0404(10) 0.0333(10) 0.0168(8) -0.0011(8) 0.0036(7) -0.0076(8)
C2 0.0330(13) 0.0336(14) 0.0139(11) -0.0049(10) 0.0005(9) -0.0030(10)
C3 0.0279(12) 0.0275(12) 0.0177(11) -0.0003(10) -0.0003(9) 0.0055(10)
C4 0.0308(13) 0.0286(12) 0.0164(11) 0.0014(10) 0.0008(9) 0.0003(10)
C5 0.0301(12) 0.0277(13) 0.0188(11) 0.0012(10) -0.0001(9) 0.0029(10)
C6 0.0314(13) 0.0248(12) 0.0146(11) 0.0013(9) -0.0024(9) 0.0028(10)
C7 0.0322(13) 0.0226(12) 0.0194(12) -0.0002(10) 0.0004(10) -0.0013(9)
O8 0.0384(10) 0.0260(9) 0.0283(9) -0.0044(7) 0.0067(7) -0.0052(8)
C9 0.0433(16) 0.0266(14) 0.0371(15) -0.0012(11) 0.0030(12) -0.0037(12)
C10 0.0379(14) 0.0250(12) 0.0163(11) -0.0035(9) -0.0016(10) 0.0002(10)
O11 0.0516(12) 0.0327(10) 0.0186(9) -0.0047(8) -0.0018(8) -0.0050(9)
C12 0.058(2) 0.0493(19) 0.0407(17) -0.0107(15) -0.0153(15) -0.0030(16)
C13 0.0359(13) 0.0310(13) 0.0138(11) 0.0010(10) 0.0010(9) 0.0006(11)
O14 0.0567(13) 0.0384(11) 0.0207(9) 0.0001(8) 0.0106(8) -0.0102(9)
C15 0.0523(17) 0.0431(17) 0.0307(15) 0.0068(13) 0.0106(13) -0.0105(14)
C16 0.0325(13) 0.0277(13) 0.0257(13) 0.0001(10) -0.0004(10) -0.0030(11)
C17 0.0335(13) 0.0261(13) 0.0202(12) -0.0010(10) -0.0026(9) -0.0013(10)
C18 0.0334(13) 0.0276(13) 0.0156(11) -0.0010(9) 0.0005(9) 0.0021(10)
C19 0.0300(13) 0.0284(13) 0.0185(11) -0.0039(10) 0.0011(9) 0.0011(10)
C20 0.0335(14) 0.0317(13) 0.0172(11) -0.0021(10) 0.0031(10) -0.0017(10)
C21 0.0356(14) 0.0399(15) 0.0221(12) -0.0040(11) 0.0039(10) -0.0059(12)
N22 0.0547(16) 0.0534(17) 0.0378(14) -0.0118(13) 0.0108(12) -0.0167(14)
C23 0.0395(14) 0.0378(15) 0.0193(12) -0.0056(11) 0.0024(11) -0.0028(12)
N24 0.0593(17) 0.0519(17) 0.0290(13) -0.0015(12) 0.0069(12) -0.0155(13)
C25 0.0365(13) 0.0276(13) 0.0188(12) -0.0031(10) 0.0026(10) 0.0042(11)
N26 0.0484(15) 0.0330(13) 0.0348(13) -0.0001(10) 0.0026(11) -0.0066(11)
C27 0.0404(14) 0.0301(14) 0.0231(12) -0.0001(11) 0.0011(10) -0.0020(11)
C28 0.0328(14) 0.0446(16) 0.0279(13) -0.0020(12) 0.0007(11) 0.0001(12)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.50(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.480(3) yes
O1 . C19 . 1.329(3) yes
C2 . C3 . 1.505(3) yes
C2 . C27 . 1.509(4) yes
C2 . C28 . 1.523(4) yes
C3 . C4 . 1.430(3) yes
C3 . C18 . 1.366(3) yes
C4 . C5 . 1.356(3) yes
C4 . H41 . 0.951 no
C5 . C6 . 1.441(3) yes
C5 . H51 . 0.959 no
C6 . C7 . 1.418(3) yes
C6 . C17 . 1.396(3) yes
C7 . O8 . 1.361(3) yes
C7 . C10 . 1.384(3) yes
O8 . C9 . 1.432(3) yes
C9 . H91 . 0.973 no
C9 . H92 . 0.965 no
C9 . H93 . 0.973 no
C10 . O11 . 1.383(3) yes
C10 . C13 . 1.397(4) yes
O11 . C12 . 1.401(4) yes
C12 . H122 . 0.977 no
C12 . H121 . 0.962 no
C12 . H123 . 0.969 no
C13 . O14 . 1.358(3) yes
C13 . C16 . 1.388(4) yes
O14 . C15 . 1.421(3) yes
C15 . H152 . 0.969 no
C15 . H153 . 0.972 no
C15 . H151 . 0.973 no
C16 . C17 . 1.371(3) yes
C16 . H161 . 0.945 no
C17 . H171 . 0.943 no
C18 . C19 . 1.435(3) yes
C18 . C25 . 1.418(4) yes
C19 . C20 . 1.373(3) yes
C20 . C21 . 1.421(4) yes
C20 . C23 . 1.416(4) yes
C21 . N22 . 1.146(4) yes
C23 . N24 . 1.144(4) yes
C25 . N26 . 1.148(3) yes
C27 . H271 . 0.962 no
C27 . H273 . 0.961 no
C27 . H272 . 0.962 no
C28 . H282 . 0.955 no
C28 . H281 . 0.961 no
C28 . H283 . 0.939 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C19 . 110.14(18) yes
O1 . C2 . C3 . 102.60(18) yes
O1 . C2 . C27 . 105.28(19) yes
C3 . C2 . C27 . 114.1(2) yes
O1 . C2 . C28 . 105.7(2) yes
C3 . C2 . C28 . 113.8(2) yes
C27 . C2 . C28 . 113.8(2) yes
C2 . C3 . C4 . 125.9(2) yes
C2 . C3 . C18 . 108.5(2) yes
C4 . C3 . C18 . 125.6(2) yes
C3 . C4 . C5 . 124.6(2) yes
C3 . C4 . H41 . 117.5 no
C5 . C4 . H41 . 117.9 no
C4 . C5 . C6 . 127.1(2) yes
C4 . C5 . H51 . 116.6 no
C6 . C5 . H51 . 116.2 no
C5 . C6 . C7 . 118.3(2) yes
C5 . C6 . C17 . 123.5(2) yes
C7 . C6 . C17 . 118.1(2) yes
C6 . C7 . O8 . 117.7(2) yes
C6 . C7 . C10 . 120.0(2) yes
O8 . C7 . C10 . 122.2(2) yes
C7 . O8 . C9 . 117.88(19) yes
O8 . C9 . H91 . 109.1 no
O8 . C9 . H92 . 109.9 no
H91 . C9 . H92 . 108.3 no
O8 . C9 . H93 . 111.0 no
H91 . C9 . H93 . 108.1 no
H92 . C9 . H93 . 110.5 no
C7 . C10 . O11 . 119.9(2) yes
C7 . C10 . C13 . 120.1(2) yes
O11 . C10 . C13 . 120.0(2) yes
C10 . O11 . C12 . 113.1(2) yes
O11 . C12 . H122 . 108.2 no
O11 . C12 . H121 . 111.1 no
H122 . C12 . H121 . 111.2 no
O11 . C12 . H123 . 107.9 no
H122 . C12 . H123 . 108.3 no
H121 . C12 . H123 . 110.0 no
C10 . C13 . O14 . 114.7(2) yes
C10 . C13 . C16 . 120.2(2) yes
O14 . C13 . C16 . 125.1(2) yes
C13 . O14 . C15 . 117.6(2) yes
O14 . C15 . H152 . 108.0 no
O14 . C15 . H153 . 110.7 no
H152 . C15 . H153 . 108.8 no
O14 . C15 . H151 . 110.0 no
H152 . C15 . H151 . 107.7 no
H153 . C15 . H151 . 111.5 no
C13 . C16 . C17 . 119.7(2) yes
C13 . C16 . H161 . 120.5 no
C17 . C16 . H161 . 119.8 no
C6 . C17 . C16 . 121.8(2) yes
C6 . C17 . H171 . 119.2 no
C16 . C17 . H171 . 119.0 no
C3 . C18 . C19 . 108.7(2) yes
C3 . C18 . C25 . 124.5(2) yes
C19 . C18 . C25 . 126.8(2) yes
C18 . C19 . O1 . 110.0(2) yes
C18 . C19 . C20 . 131.1(2) yes
O1 . C19 . C20 . 118.9(2) yes
C19 . C20 . C21 . 122.7(2) yes
C19 . C20 . C23 . 119.7(2) yes
C21 . C20 . C23 . 117.6(2) yes
C20 . C21 . N22 . 177.0(3) yes
C20 . C23 . N24 . 178.9(3) yes
C18 . C25 . N26 . 176.2(3) yes
C2 . C27 . H271 . 110.1 no
C2 . C27 . H273 . 109.4 no
H271 . C27 . H273 . 109.5 no
C2 . C27 . H272 . 112.3 no
H271 . C27 . H272 . 108.8 no
H273 . C27 . H272 . 106.7 no
C2 . C28 . H282 . 111.0 no
C2 . C28 . H281 . 110.0 no
H282 . C28 . H281 . 108.0 no
C2 . C28 . H283 . 109.1 no
H282 . C28 . H283 . 108.8 no
H281 . C28 . H283 . 110.0 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C16 . H161 . N22 2_676 167.60(8) 0.945 2.561 3.490(4) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 04/04/14 at 09:36:07
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) H   (  92,X'S) H   (  93,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) H   ( 123,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 153,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) H   ( 273,X'S) H   ( 272,X'S) 
RIDE C   (  28,X'S) H   ( 282,X'S) H   ( 281,X'S) H   ( 283,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 04/04/14 at 09:36:07
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1429531'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   17.1210(10)
_cell_length_b                   6.9428(5)
_cell_length_c                   15.4460(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1836.0(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n m a '
_symmetry_space_group_name_Hall  '-P 2ac 2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
-x,y+1/2,-z
x,-y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C17 N4 O5 
# Dc =      1.23 Fooo =    728.00 Mu =      8.15 M =    170.11
# Found Formula = C20 H17 N3 O3 
# Dc =      1.26 FOOO =    728.00 Mu =      7.06 M =    173.69

_chemical_formula_sum            'C20 H17 N3 O3'
_chemical_formula_moiety         'C20 H17 N3 O3'
_chemical_compound_source        ?
_chemical_formula_weight         347.37


_cell_measurement_reflns_used    5414
_cell_measurement_theta_min      5.1410
_cell_measurement_theta_max      66.9540
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.144
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_max          0.553

_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.706

# Sheldrick geometric approximatio 0.79 0.90 
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector_area_resol_mean 10.4678
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            11309
_reflns_number_total             1772
_diffrn_reflns_av_R_equivalents  0.063
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1772 
# Theoretical number of reflections is about 3273 


_diffrn_reflns_theta_min         3.854
_diffrn_reflns_theta_max         67.001
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        67.001
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              0
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.19
_oxford_diffrn_Wilson_scale      0.08

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.25


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         1761
_refine_ls_number_restraints     14
_refine_ls_number_parameters     162
_oxford_refine_ls_R_factor_ref   0.0422
_refine_ls_wR_factor_ref         0.1128
_refine_ls_goodness_of_fit_ref   1.0111
_refine_ls_shift/su_max          0.0006934
_refine_ls_shift/su_mean         0.0000383


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1761
_refine_ls_R_factor_all          0.0422
_refine_ls_wR_factor_all         0.1128

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1599
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_gt          0.1081

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.152E+04 0.257E+04 0.157E+04 646. 143. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.54692(6) 0.2500 0.72805(7) 0.0311 1.0000 Uani S T . . . .
C2 C 0.47402(9) 0.2500 0.67611(11) 0.0277 1.0000 Uani S T . . . .
C3 C 0.42911(7) 0.06902(18) 0.70079(8) 0.0347 1.0000 Uani . . . . . .
H31 H 0.3790 0.0682 0.6693 0.0508 1.0000 Uiso R . . . . .
H33 H 0.4579 -0.0456 0.6854 0.0519 1.0000 Uiso R . . . . .
H32 H 0.4182 0.0710 0.7616 0.0510 1.0000 Uiso R . . . . .
C4 C 0.50469(10) 0.2500 0.58430(10) 0.0257 1.0000 Uani S T . . . .
C5 C 0.46144(9) 0.250000(7) 0.50485(11) 0.0285 1.0000 Uani S T . . . .
C6 C 0.38363(10) 0.250000(7) 0.49438(11) 0.0283 1.0000 Uani S T . . . .
C7 C 0.34429(10) 0.2500 0.40987(10) 0.0271 1.0000 Uani S T . . . .
C8 C 0.38568(10) 0.250000(7) 0.33229(11) 0.0294 1.0000 Uani S T . . . .
C9 C 0.34619(10) 0.2500 0.25320(11) 0.0293 1.0000 Uani S T . . . .
O10 O 0.39265(7) 0.2500 0.18178(8) 0.0418 1.0000 Uani S T . . . .
C11 C 0.35584(12) 0.250000(7) 0.09847(11) 0.0406 1.0000 Uani S T . . . .
H113 H 0.3974 0.2500 0.0565 0.0610 1.0000 Uiso RS . . . . .
H112 H 0.3244 0.1350 0.0919 0.0603 1.0000 Uiso R . . . . .
C12 C 0.26522(10) 0.250000(7) 0.25152(11) 0.0287 1.0000 Uani S T . . . .
C13 C 0.22412(10) 0.2500 0.33006(11) 0.0275 1.0000 Uani S T . . . .
C14 C 0.26260(10) 0.250000(7) 0.40915(11) 0.0285 1.0000 Uani S T . . . .
H141 H 0.2341 0.2500 0.4612 0.0346 1.0000 Uiso RS . . . . .
O15 O 0.14510(7) 0.2500 0.32177(8) 0.0357 1.0000 Uani S T . . . .
C16 C 0.09973(11) 0.250000(7) 0.39949(14) 0.0472 1.0000 Uani S T . . . .
H162 H 0.0450 0.2500 0.3820 0.0697 1.0000 Uiso RS . . . . .
H163 H 0.1121 0.3666 0.4334 0.0703 1.0000 Uiso R . . . . .
H121 H 0.2378 0.2500 0.1983 0.0348 1.0000 Uiso RS . . . . .
H81 H 0.4409 0.2500 0.3303 0.0356 1.0000 Uiso RS . . . . .
H61 H 0.3503 0.2500 0.5448 0.0341 1.0000 Uiso RS . . . . .
H51 H 0.4930 0.2500 0.4535 0.0350 1.0000 Uiso RS . . . . .
C17 C 0.58414(10) 0.2500 0.58738(10) 0.0255 1.0000 Uani S T . . . .
C18 C 0.60942(10) 0.2500 0.67686(10) 0.0257 1.0000 Uani S T . . . .
C19 C 0.68327(10) 0.2500 0.71012(10) 0.0284 1.0000 Uani S T . . . .
C20 C 0.69587(10) 0.2500 0.80141(12) 0.0346 1.0000 Uani S T . . . .
N21 N 0.70891(11) 0.2500 0.87420(11) 0.0508 1.0000 Uani S T . . . .
C22 C 0.75106(10) 0.2500 0.65648(11) 0.0308 1.0000 Uani S T . . . .
N23 N 0.80748(9) 0.2500 0.61646(11) 0.0427 1.0000 Uani S T . . . .
C24 C 0.63295(9) 0.2500 0.51247(11) 0.0290 1.0000 Uani S T . . . .
N25 N 0.66693(9) 0.2500 0.44903(10) 0.0421 1.0000 Uani S T . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0234(6) 0.0468(7) 0.0231(6) 0.0000 -0.0018(4) 0.0000
C2 0.0204(8) 0.0382(9) 0.0244(8) 0.0000 -0.0007(6) 0.0000
C3 0.0307(6) 0.0376(7) 0.0358(6) 0.0036(5) 0.0040(5) -0.0012(5)
C4 0.0245(8) 0.0281(8) 0.0245(8) 0.0000 -0.0015(6) 0.0000
C5 0.0248(8) 0.0358(9) 0.0248(8) 0.0000 -0.0023(7) 0.0000
C6 0.0262(9) 0.0316(8) 0.0272(8) 0.0000 -0.0016(7) 0.0000
C7 0.0265(8) 0.0269(8) 0.0279(9) 0.0000 -0.0038(6) 0.0000
C8 0.0209(8) 0.0353(9) 0.0320(9) 0.0000 -0.0024(6) 0.0000
C9 0.0270(9) 0.0340(8) 0.0270(8) 0.0000 0.0002(7) 0.0000
O10 0.0277(7) 0.0700(9) 0.0277(7) 0.0000 0.0002(5) 0.0000
C11 0.0370(10) 0.0592(12) 0.0255(9) 0.0000 -0.0015(7) 0.0000
C12 0.0266(9) 0.0320(8) 0.0275(8) 0.0000 -0.0067(7) 0.0000
C13 0.0240(9) 0.0276(8) 0.0310(8) 0.0000 -0.0045(7) 0.0000
C14 0.0258(9) 0.0318(8) 0.0278(9) 0.0000 -0.0006(6) 0.0000
O15 0.0214(6) 0.0511(8) 0.0346(7) 0.0000 -0.0034(5) 0.0000
C16 0.0234(9) 0.0749(14) 0.0433(10) 0.0000 0.0028(8) 0.0000
C17 0.0240(8) 0.0296(8) 0.0230(8) 0.0000 -0.0005(6) 0.0000
C18 0.0255(9) 0.0285(8) 0.0232(8) 0.0000 -0.0004(6) 0.0000
C19 0.0276(8) 0.0300(8) 0.0275(8) 0.0000 -0.0059(7) 0.0000
C20 0.0302(9) 0.0402(10) 0.0335(10) 0.0000 -0.0080(7) 0.0000
N21 0.0546(11) 0.0634(11) 0.0345(10) 0.0000 -0.0168(8) 0.0000
C22 0.0249(9) 0.0334(9) 0.0341(9) 0.0000 -0.0088(7) 0.0000
N23 0.0281(8) 0.0536(10) 0.0464(9) 0.0000 -0.0025(7) 0.0000
C24 0.0219(8) 0.0376(9) 0.0275(9) 0.0000 -0.0018(7) 0.0000
N25 0.0295(8) 0.0659(11) 0.0308(8) 0.0000 0.0017(7) 0.0000

_refine_ls_extinction_coef       114(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          4.05(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.4837(19) yes
O1 . C18 . 1.330(2) yes
C2 . C3 8_555 1.5216(15) yes
C2 . C3 . 1.5216(15) yes
C2 . C4 . 1.512(2) yes
C3 . H31 . 0.987 no
C3 . H33 . 0.966 no
C3 . H32 . 0.958 no
C4 . C5 . 1.433(2) yes
C4 . C17 . 1.361(2) yes
C5 . C6 . 1.342(2) yes
C5 . H51 . 0.960 no
C6 . C7 . 1.469(2) yes
C6 . H61 . 0.965 no
C7 . C8 . 1.392(2) yes
C7 . C14 . 1.399(2) yes
C8 . C9 . 1.396(2) yes
C8 . H81 . 0.947 no
C9 . O10 . 1.360(2) yes
C9 . C12 . 1.387(2) yes
O10 . C11 . 1.433(2) yes
C11 . H112 8_555 0.968 no
C11 . H113 . 0.962 no
C11 . H112 . 0.968 no
C12 . C13 . 1.402(2) yes
C12 . H121 . 0.947 no
C13 . C14 . 1.388(2) yes
C13 . O15 . 1.359(2) yes
C14 . H141 . 0.941 no
O15 . C16 . 1.430(2) yes
C16 . H163 8_555 0.987 no
C16 . H162 . 0.976 no
C16 . H163 . 0.987 no
C17 . C18 . 1.448(2) yes
C17 . C24 . 1.427(2) yes
C18 . C19 . 1.365(2) yes
C19 . C20 . 1.426(2) yes
C19 . C22 . 1.426(2) yes
C20 . N21 . 1.146(2) yes
C22 . N23 . 1.147(2) yes
C24 . N25 . 1.140(2) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C18 . 110.81(12) yes
C3 8_555 C2 . O1 . 106.84(9) yes
C3 8_555 C2 . C3 . 111.33(14) yes
O1 . C2 . C3 . 106.84(9) yes
C3 8_555 C2 . C4 . 114.23(8) yes
O1 . C2 . C4 . 102.41(12) yes
C3 . C2 . C4 . 114.23(8) yes
C2 . C3 . H31 . 108.7 no
C2 . C3 . H33 . 111.1 no
H31 . C3 . H33 . 108.5 no
C2 . C3 . H32 . 109.4 no
H31 . C3 . H32 . 108.3 no
H33 . C3 . H32 . 110.6 no
C2 . C4 . C5 . 128.57(15) yes
C2 . C4 . C17 . 108.32(13) yes
C5 . C4 . C17 . 123.11(14) yes
C4 . C5 . C6 . 128.02(16) yes
C4 . C5 . H51 . 114.6 no
C6 . C5 . H51 . 117.4 no
C5 . C6 . C7 . 124.21(16) yes
C5 . C6 . H61 . 119.3 no
C7 . C6 . H61 . 116.5 no
C6 . C7 . C8 . 122.11(15) yes
C6 . C7 . C14 . 117.74(15) yes
C8 . C7 . C14 . 120.15(15) yes
C7 . C8 . C9 . 120.43(15) yes
C7 . C8 . H81 . 122.4 no
C9 . C8 . H81 . 117.1 no
C8 . C9 . O10 . 115.24(14) yes
C8 . C9 . C12 . 120.04(16) yes
O10 . C9 . C12 . 124.72(15) yes
C9 . O10 . C11 . 118.11(13) yes
O10 . C11 . H112 8_555 109.8 no
O10 . C11 . H113 . 106.2 no
H112 8_555 C11 . H113 . 109.9 no
O10 . C11 . H112 . 109.8 no
H112 8_555 C11 . H112 . 111.2 no
H113 . C11 . H112 . 109.9 no
C9 . C12 . C13 . 119.04(16) yes
C9 . C12 . H121 . 120.8 no
C13 . C12 . H121 . 120.2 no
C12 . C13 . C14 . 121.55(16) yes
C12 . C13 . O15 . 114.71(14) yes
C14 . C13 . O15 . 123.74(15) yes
C7 . C14 . C13 . 118.79(15) yes
C7 . C14 . H141 . 120.8 no
C13 . C14 . H141 . 120.4 no
C13 . O15 . C16 . 117.50(14) yes
H163 8_555 C16 . O15 . 109.2 no
H163 8_555 C16 . H162 . 110.7 no
O15 . C16 . H162 . 106.8 no
H163 8_555 C16 . H163 . 110.2 no
O15 . C16 . H163 . 109.2 no
H162 . C16 . H163 . 110.7 no
C4 . C17 . C18 . 109.40(13) yes
C4 . C17 . C24 . 123.83(14) yes
C18 . C17 . C24 . 126.77(15) yes
C17 . C18 . O1 . 109.07(13) yes
C17 . C18 . C19 . 129.50(15) yes
O1 . C18 . C19 . 121.43(14) yes
C18 . C19 . C20 . 120.81(15) yes
C18 . C19 . C22 . 122.36(14) yes
C20 . C19 . C22 . 116.82(15) yes
C19 . C20 . N21 . 177.5(2) yes
C19 . C22 . N23 . 177.09(19) yes
C17 . C24 . N25 . 174.86(17) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C14 . H141 . N21 4_456 158.32(6) 0.941 2.579 3.4704(16) yes
C12 . H121 . N25 4_455 178.35(5) 0.947 2.579 3.5253(16) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 30/10/13 at 17:11:01
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  33,X'S) H   (  32,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 163,X'S) H   ( 162,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 30/10/13 at 17:11:01
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mi7p106
_database_code_depnum_ccdc_archive 'CCDC 1429532'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

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

_cell_length_a                   16.2981(11)
_cell_length_b                   16.4911(9)
_cell_length_c                   7.1281(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.738(6)
_cell_angle_gamma                90.00
_cell_volume                     1882.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    8257
_cell_measurement_theta_min      3.7880
_cell_measurement_theta_max      67.1510

_exptl_crystal_description       octahedral
_exptl_crystal_colour            'translucent intense red'
_exptl_crystal_size_max          0.5212
_exptl_crystal_size_mid          0.2525
_exptl_crystal_size_min          0.1247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51539
_exptl_absorpt_correction_T_max  1.00000
_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_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4685
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24328
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.85
_diffrn_reflns_theta_max         67.11
_reflns_number_total             3349
_reflns_number_gt                2857
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Gemini, (Oxford Diffraction, 2006)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXLe (Sheldrick, 2011)'
_computing_publication_material  'SHELXLe (Sheldrick, 2011)'

_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)+(0.1471P)²+0.5106P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2046
_refine_ls_wR_factor_gt          0.1925
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.007
_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
O1 O 0.67639(10) 0.05863(9) 0.1655(2) 0.0286(4) Uani 1 1 d . . .
C1 C 0.59519(16) 0.03267(15) 0.1867(4) 0.0382(6) Uani 1 1 d . . .
H1A H 0.5542 0.0560 0.0872 0.057 Uiso 1 1 calc R . .
H1B H 0.5847 0.0499 0.3087 0.057 Uiso 1 1 calc R . .
H1C H 0.5921 -0.0254 0.1786 0.057 Uiso 1 1 calc R . .
C2 C 0.86492(15) 0.51870(14) -0.0633(3) 0.0270(5) Uani 1 1 d . . .
H2A H 0.8168 0.5358 -0.1538 0.040 Uiso 1 1 calc R . .
H2B H 0.8697 0.4607 -0.0673 0.040 Uiso 1 1 calc R . .
H2C H 0.9141 0.5431 -0.0946 0.040 Uiso 1 1 calc R . .
C3 C 0.93382(15) 0.20434(14) 0.1167(3) 0.0307(5) Uani 1 1 d . . .
H3A H 0.9165 0.1714 0.0053 0.046 Uiso 1 1 calc R . .
H3B H 0.9409 0.1708 0.2287 0.046 Uiso 1 1 calc R . .
H3C H 0.9858 0.2304 0.1092 0.046 Uiso 1 1 calc R . .
C4 C 0.79038(13) 0.75091(13) 0.1893(3) 0.0223(5) Uani 1 1 d . . .
C5 C 0.51756(14) 0.32279(14) 0.1947(3) 0.0275(5) Uani 1 1 d . . .
H5A H 0.4867 0.3725 0.1921 0.041 Uiso 1 1 calc R . .
H5B H 0.5150 0.2939 0.3104 0.041 Uiso 1 1 calc R . .
H5C H 0.4938 0.2900 0.0869 0.041 Uiso 1 1 calc R . .
N1 N 0.58769(13) 0.62745(13) 0.2729(3) 0.0333(5) Uani 1 1 d . . .
C6 C 0.92564(14) 0.51475(14) 0.2920(3) 0.0276(5) Uani 1 1 d . . .
H6A H 0.9259 0.4565 0.2927 0.041 Uiso 1 1 calc R . .
H6B H 0.9172 0.5343 0.4138 0.041 Uiso 1 1 calc R . .
H6C H 0.9781 0.5343 0.2676 0.041 Uiso 1 1 calc R . .
C7 C 0.76927(14) 0.53146(13) 0.1795(3) 0.0221(5) Uani 1 1 d . . .
C8 C 0.85547(14) 0.54488(12) 0.1367(3) 0.0229(5) Uani 1 1 d . . .
C9 C 0.71956(14) 0.79323(13) 0.2292(3) 0.0238(5) Uani 1 1 d . . .
N2 N 0.66455(13) 0.83039(12) 0.2630(3) 0.0313(5) Uani 1 1 d . . .
C10 C 0.76613(14) 0.38418(13) 0.1604(3) 0.0226(5) Uani 1 1 d . . .
H10 H 0.8200 0.3892 0.1362 0.027 Uiso 1 1 calc R . .
C11 C 0.63239(14) 0.19796(13) 0.1813(3) 0.0239(5) Uani 1 1 d . . .
H11 H 0.5784 0.1837 0.1934 0.029 Uiso 1 1 calc R . .
C12 C 0.73519(13) 0.60620(13) 0.2049(3) 0.0222(5) Uani 1 1 d . . .
C13 C 0.65372(14) 0.61911(13) 0.2434(3) 0.0245(5) Uani 1 1 d . . .
C14 C 0.79416(13) 0.66753(13) 0.1799(3) 0.0220(5) Uani 1 1 d . . .
C15 C 0.69138(14) 0.13909(13) 0.1656(3) 0.0227(5) Uani 1 1 d . . .
C16 C 0.77246(14) 0.15904(13) 0.1467(3) 0.0231(5) Uani 1 1 d . . .
H16 H 0.8109 0.1185 0.1355 0.028 Uiso 1 1 calc R . .
C17 C 0.79498(13) 0.23944(13) 0.1447(3) 0.0221(5) Uani 1 1 d . . .
C18 C 0.85981(14) 0.79821(13) 0.1580(3) 0.0231(5) Uani 1 1 d . . .
N3 N 0.91532(13) 0.83718(12) 0.1350(3) 0.0295(5) Uani 1 1 d . . .
C19 C 0.65578(13) 0.27866(13) 0.1784(3) 0.0219(5) Uani 1 1 d . . .
C20 C 0.73711(14) 0.30242(13) 0.1616(3) 0.0225(5) Uani 1 1 d . . .
C21 C 0.72911(14) 0.45573(13) 0.1884(3) 0.0235(5) Uani 1 1 d . . .
H21 H 0.6753 0.4550 0.2144 0.028 Uiso 1 1 calc R . .
O2 O 0.60221(9) 0.34044(9) 0.1867(2) 0.0262(4) Uani 1 1 d . . .
O3 O 0.87207(9) 0.26418(9) 0.1269(2) 0.0254(4) Uani 1 1 d . . .
O4 O 0.86279(9) 0.63440(9) 0.1388(2) 0.0234(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0339(9) 0.0217(8) 0.0305(8) -0.0002(6) 0.0066(7) -0.0031(6)
C1 0.0346(14) 0.0266(12) 0.0538(16) 0.0030(10) 0.0095(11) -0.0029(10)
C2 0.0379(13) 0.0251(11) 0.0208(11) -0.0019(8) 0.0127(9) -0.0011(9)
C3 0.0299(13) 0.0304(12) 0.0320(12) -0.0046(9) 0.0065(9) 0.0037(9)
C4 0.0295(12) 0.0232(10) 0.0146(10) -0.0001(7) 0.0051(8) 0.0006(8)
C5 0.0313(12) 0.0294(11) 0.0222(11) -0.0003(8) 0.0062(9) 0.0006(9)
N1 0.0332(12) 0.0371(11) 0.0314(11) 0.0011(8) 0.0106(8) 0.0020(8)
C6 0.0317(12) 0.0244(11) 0.0270(11) -0.0024(8) 0.0061(9) 0.0012(9)
C7 0.0299(12) 0.0257(11) 0.0106(9) 0.0005(7) 0.0040(8) 0.0013(8)
C8 0.0308(12) 0.0187(10) 0.0198(10) -0.0009(7) 0.0066(8) -0.0011(8)
C9 0.0318(12) 0.0231(11) 0.0157(10) 0.0021(8) 0.0025(8) -0.0010(9)
N2 0.0342(11) 0.0311(11) 0.0293(10) -0.0007(8) 0.0076(8) 0.0038(8)
C10 0.0287(11) 0.0285(11) 0.0113(9) 0.0016(7) 0.0056(8) -0.0024(9)
C11 0.0321(12) 0.0251(11) 0.0147(10) 0.0014(8) 0.0051(8) -0.0012(9)
C12 0.0288(11) 0.0252(11) 0.0133(10) 0.0010(7) 0.0057(8) 0.0004(8)
C13 0.0312(12) 0.0228(10) 0.0194(10) 0.0004(8) 0.0043(9) -0.0016(8)
C14 0.0292(12) 0.0252(11) 0.0118(9) 0.0009(7) 0.0042(8) 0.0022(8)
C15 0.0329(12) 0.0230(11) 0.0112(9) 0.0009(7) 0.0018(8) -0.0039(8)
C16 0.0311(12) 0.0231(11) 0.0149(10) -0.0004(8) 0.0041(8) 0.0008(8)
C17 0.0286(12) 0.0273(11) 0.0106(9) -0.0004(7) 0.0039(8) -0.0023(8)
C18 0.0317(12) 0.0227(11) 0.0150(10) -0.0012(8) 0.0043(8) 0.0031(9)
N3 0.0380(11) 0.0271(10) 0.0250(10) -0.0012(7) 0.0104(8) -0.0020(8)
C19 0.0315(12) 0.0247(11) 0.0099(9) 0.0002(7) 0.0051(8) 0.0014(8)
C20 0.0307(12) 0.0253(11) 0.0115(9) 0.0005(7) 0.0042(8) 0.0009(9)
C21 0.0287(12) 0.0260(11) 0.0162(10) 0.0004(8) 0.0055(8) -0.0010(8)
O2 0.0287(9) 0.0246(8) 0.0266(8) 0.0003(6) 0.0085(6) 0.0020(6)
O3 0.0279(9) 0.0256(8) 0.0235(8) -0.0010(6) 0.0072(6) 0.0000(6)
O4 0.0287(8) 0.0199(8) 0.0232(8) -0.0015(5) 0.0093(6) -0.0005(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.349(3) . ?
O1 C1 1.425(3) . ?
C2 C8 1.525(3) . ?
C3 O3 1.421(3) . ?
C4 C14 1.379(3) . ?
C4 C9 1.422(3) . ?
C4 C18 1.426(3) . ?
C5 O2 1.421(3) . ?
N1 C13 1.143(3) . ?
C6 C8 1.519(3) . ?
C7 C12 1.378(3) . ?
C7 C21 1.417(3) . ?
C7 C8 1.508(3) . ?
C8 O4 1.481(2) . ?
C9 N2 1.148(3) . ?
C10 C21 1.357(3) . ?
C10 C20 1.429(3) . ?
C11 C19 1.385(3) . ?
C11 C15 1.385(3) . ?
C12 C13 1.421(3) . ?
C12 C14 1.429(3) . ?
C14 O4 1.326(2) . ?
C15 C16 1.393(3) . ?
C16 C17 1.376(3) . ?
C17 O3 1.349(3) . ?
C17 C20 1.423(3) . ?
C18 N3 1.146(3) . ?
C19 O2 1.350(3) . ?
C19 C20 1.409(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
C15 O1 C1 117.84(18) . . ?
C14 C4 C9 123.0(2) . . ?
C14 C4 C18 119.61(19) . . ?
C9 C4 C18 117.4(2) . . ?
C12 C7 C21 125.6(2) . . ?
C12 C7 C8 107.99(18) . . ?
C21 C7 C8 126.44(19) . . ?
O4 C8 C7 102.74(16) . . ?
O4 C8 C6 105.69(16) . . ?
C7 C8 C6 114.08(17) . . ?
O4 C8 C2 105.66(16) . . ?
C7 C8 C2 114.05(18) . . ?
C6 C8 C2 113.26(18) . . ?
N2 C9 C4 177.0(2) . . ?
C21 C10 C20 131.5(2) . . ?
C19 C11 C15 118.4(2) . . ?
C7 C12 C13 125.0(2) . . ?
C7 C12 C14 108.64(19) . . ?
C13 C12 C14 126.33(19) . . ?
N1 C13 C12 178.2(2) . . ?
O4 C14 C4 117.97(19) . . ?
O4 C14 C12 110.53(18) . . ?
C4 C14 C12 131.5(2) . . ?
O1 C15 C11 124.1(2) . . ?
O1 C15 C16 114.04(19) . . ?
C11 C15 C16 121.8(2) . . ?
C17 C16 C15 119.2(2) . . ?
O3 C17 C16 123.2(2) . . ?
O3 C17 C20 115.51(18) . . ?
C16 C17 C20 121.3(2) . . ?
N3 C18 C4 178.9(2) . . ?
O2 C19 C11 122.8(2) . . ?
O2 C19 C20 114.85(18) . . ?
C11 C19 C20 122.3(2) . . ?
C19 C20 C17 116.95(19) . . ?
C19 C20 C10 125.5(2) . . ?
C17 C20 C10 117.56(19) . . ?
C10 C21 C7 122.6(2) . . ?
C19 O2 C5 119.18(17) . . ?
C17 O3 C3 118.40(17) . . ?
C14 O4 C8 110.08(15) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.11
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.111
_exptl_crystal_preparation       Luminescent
