# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4


_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_absolute_configuration ad
#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_Int_Tables_number      43
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/4-X,1/4+Y,1/4+Z
3 1/4+X,1/4-Y,1/4+Z
4 1/2-X,-Y,1/2+Z
5 +X,1/2+Y,1/2+Z
6 1/4-X,3/4+Y,3/4+Z
7 1/4+X,3/4-Y,3/4+Z
8 1/2-X,1/2-Y,+Z
9 1/2+X,+Y,1/2+Z
10 3/4-X,1/4+Y,3/4+Z
11 3/4+X,1/4-Y,3/4+Z
12 -X,-Y,+Z
13 1/2+X,1/2+Y,+Z
14 3/4-X,3/4+Y,1/4+Z
15 3/4+X,3/4-Y,1/4+Z
16 -X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   27.454(9)
_cell_length_b                   32.678(11)
_cell_length_c                   6.833(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     6130(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      21.19
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2592.00
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  0.978

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            19918
_diffrn_reflns_av_R_equivalents  0.1303
_diffrn_reflns_theta_max         68.637
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2797
_reflns_number_gt                2604
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1415
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2797
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0730P)²+4.8151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1055 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(2)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.57728(10) 0.70012(8) 0.1921(4) 0.0442(7) Uani 1 16 0 d . . .
O6 O 0.48477(10) 0.63375(8) 0.8718(4) 0.0479(7) Uani 1 16 0 d . . .
O7 O 0.55484(9) 0.60857(7) 0.7455(4) 0.0378(6) Uani 1 16 0 d . . .
N1 N 0.52202(11) 0.66578(9) 0.6150(5) 0.0379(7) Uani 1 16 0 d . . .
N2 N 0.56277(10) 0.66747(9) 0.4900(4) 0.0349(7) Uani 1 16 0 d . . .
C3 C 0.54874(14) 0.68974(11) 0.3206(5) 0.0367(8) Uani 1 16 0 d . . .
C4 C 0.49711(14) 0.69672(11) 0.3378(6) 0.0383(8) Uani 1 16 0 d . . .
C5 C 0.48185(13) 0.68251(11) 0.5138(6) 0.0385(8) Uani 1 16 0 d . . .
C6 C 0.51753(12) 0.63508(11) 0.7562(6) 0.0371(8) Uani 1 16 0 d . . .
C8 C 0.56038(13) 0.58162(11) 0.9065(5) 0.0363(8) Uani 1 16 0 d . . .
C9 C 0.55419(17) 0.54074(12) 0.8754(6) 0.0498(10) Uani 1 16 0 d . . .
C10 C 0.56275(19) 0.51422(14) 1.0290(7) 0.0584(12) Uani 1 16 0 d . . .
C11 C 0.57709(15) 0.52877(14) 1.2105(6) 0.0497(10) Uani 1 16 0 d . . .
C12 C 0.58323(14) 0.57008(12) 1.2382(6) 0.0436(9) Uani 1 16 0 d . . .
C13 C 0.57496(14) 0.59706(11) 1.0839(6) 0.0388(8) Uani 1 16 0 d . . .
C14 C 0.61041(13) 0.67157(11) 0.5723(5) 0.0341(8) Uani 1 16 0 d . . .
C15 C 0.61736(14) 0.68634(11) 0.7617(5) 0.0378(8) Uani 1 16 0 d . . .
C16 C 0.66420(15) 0.68911(12) 0.8349(6) 0.0460(9) Uani 1 16 0 d . . .
C17 C 0.70402(15) 0.67923(13) 0.7191(7) 0.0485(10) Uani 1 16 0 d . . .
C18 C 0.69646(15) 0.66476(12) 0.5303(6) 0.0437(9) Uani 1 16 0 d . . .
C19 C 0.65019(13) 0.66021(11) 0.4580(6) 0.0381(8) Uani 1 16 0 d . . .
C20 C 0.46794(16) 0.71720(13) 0.1815(7) 0.0513(10) Uani 1 16 0 d . . .
C21 C 0.43204(14) 0.68216(14) 0.5957(7) 0.0514(11) Uani 1 16 0 d . . .
H9 H 0.54423 0.53074 0.75113 0.0598 Uiso 1 16 0 calc R . .
H10 H 0.55875 0.48562 1.00997 0.0701 Uiso 1 16 0 calc R . .
H11 H 0.58266 0.51026 1.31535 0.0597 Uiso 1 16 0 calc R . .
H12 H 0.59308 0.58023 1.36231 0.0524 Uiso 1 16 0 calc R . .
H13 H 0.57935 0.62567 1.10109 0.0466 Uiso 1 16 0 calc R . .
H15 H 0.59029 0.69437 0.83935 0.0453 Uiso 1 16 0 calc R . .
H16 H 0.66917 0.69788 0.96598 0.0552 Uiso 1 16 0 calc R . .
H17 H 0.73616 0.68233 0.76842 0.0582 Uiso 1 16 0 calc R . .
H18 H 0.72362 0.65796 0.45057 0.0525 Uiso 1 16 0 calc R . .
H19 H 0.64528 0.64935 0.33053 0.0458 Uiso 1 16 0 calc R . .
H20A H 0.4463 0.73756 0.24088 0.0616 Uiso 1 16 0 calc R . .
H20B H 0.44844 0.69671 0.112 0.0616 Uiso 1 16 0 calc R . .
H20C H 0.48993 0.73077 0.08902 0.0616 Uiso 1 16 0 calc R . .
H21A H 0.43196 0.69615 0.72252 0.0617 Uiso 1 16 0 calc R . .
H21B H 0.42124 0.65381 0.61303 0.0617 Uiso 1 16 0 calc R . .
H21C H 0.40989 0.69628 0.50576 0.0617 Uiso 1 16 0 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O3 C3 1.225(5) yes . .
O6 C6 1.198(5) yes . .
O7 C6 1.343(4) yes . .
O7 C8 1.417(4) yes . .
N1 N2 1.408(4) yes . .
N1 C5 1.412(5) yes . .
N1 C6 1.397(5) yes . .
N2 C3 1.420(5) yes . .
N2 C14 1.430(5) yes . .
C3 C4 1.440(5) yes . .
C4 C5 1.355(5) yes . .
C4 C20 1.493(6) yes . .
C5 C21 1.478(5) yes . .
C8 C9 1.363(5) yes . .
C8 C13 1.372(5) yes . .
C9 C10 1.381(6) yes . .
C10 C11 1.385(6) yes . .
C11 C12 1.374(6) yes . .
C12 C13 1.393(6) yes . .
C14 C15 1.395(5) yes . .
C14 C19 1.393(5) yes . .
C15 C16 1.383(6) yes . .
C16 C17 1.388(6) yes . .
C17 C18 1.389(6) yes . .
C18 C19 1.371(5) yes . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C15 H15 0.950 no . .
C16 H16 0.950 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20A 0.980 no . .
C20 H20B 0.980 no . .
C20 H20C 0.980 no . .
C21 H21A 0.980 no . .
C21 H21B 0.980 no . .
C21 H21C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C6 O7 C8 116.1(3) yes . . .
N2 N1 C5 108.0(3) yes . . .
N2 N1 C6 121.1(3) yes . . .
C5 N1 C6 123.2(3) yes . . .
N1 N2 C3 107.4(3) yes . . .
N1 N2 C14 119.5(3) yes . . .
C3 N2 C14 121.3(3) yes . . .
O3 C3 N2 123.5(3) yes . . .
O3 C3 C4 130.1(3) yes . . .
N2 C3 C4 106.4(3) yes . . .
C3 C4 C5 108.8(3) yes . . .
C3 C4 C20 122.7(3) yes . . .
C5 C4 C20 128.5(4) yes . . .
N1 C5 C4 109.0(3) yes . . .
N1 C5 C21 122.3(3) yes . . .
C4 C5 C21 128.7(4) yes . . .
O6 C6 O7 125.8(3) yes . . .
O6 C6 N1 123.2(3) yes . . .
O7 C6 N1 111.0(3) yes . . .
O7 C8 C9 118.3(3) yes . . .
O7 C8 C13 119.2(3) yes . . .
C9 C8 C13 122.3(4) yes . . .
C8 C9 C10 118.4(4) yes . . .
C9 C10 C11 120.9(4) yes . . .
C10 C11 C12 119.7(4) yes . . .
C11 C12 C13 119.8(4) yes . . .
C8 C13 C12 118.9(3) yes . . .
N2 C14 C15 121.5(3) yes . . .
N2 C14 C19 118.2(3) yes . . .
C15 C14 C19 120.4(3) yes . . .
C14 C15 C16 119.1(4) yes . . .
C15 C16 C17 120.7(4) yes . . .
C16 C17 C18 119.4(4) yes . . .
C17 C18 C19 120.7(4) yes . . .
C14 C19 C18 119.7(4) yes . . .
C8 C9 H9 120.821 no . . .
C10 C9 H9 120.824 no . . .
C9 C10 H10 119.555 no . . .
C11 C10 H10 119.560 no . . .
C10 C11 H11 120.149 no . . .
C12 C11 H11 120.144 no . . .
C11 C12 H12 120.073 no . . .
C13 C12 H12 120.080 no . . .
C8 C13 H13 120.551 no . . .
C12 C13 H13 120.551 no . . .
C14 C15 H15 120.455 no . . .
C16 C15 H15 120.484 no . . .
C15 C16 H16 119.628 no . . .
C17 C16 H16 119.647 no . . .
C16 C17 H17 120.297 no . . .
C18 C17 H17 120.295 no . . .
C17 C18 H18 119.667 no . . .
C19 C18 H18 119.670 no . . .
C14 C19 H19 120.146 no . . .
C18 C19 H19 120.160 no . . .
C4 C20 H20A 109.468 no . . .
C4 C20 H20B 109.467 no . . .
C4 C20 H20C 109.484 no . . .
H20A C20 H20B 109.472 no . . .
H20A C20 H20C 109.467 no . . .
H20B C20 H20C 109.470 no . . .
C5 C21 H21A 109.477 no . . .
C5 C21 H21B 109.464 no . . .
C5 C21 H21C 109.471 no . . .
H21A C21 H21B 109.464 no . . .
H21A C21 H21C 109.479 no . . .
H21B C21 H21C 109.473 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 O7 C8 C9 115.2(3) no . . . .
C6 O7 C8 C13 -69.3(4) no . . . .
C8 O7 C6 O6 -12.3(5) no . . . .
C8 O7 C6 N1 166.4(2) no . . . .
N2 N1 C5 C4 -4.0(4) no . . . .
N2 N1 C5 C21 174.4(3) no . . . .
C5 N1 N2 C3 6.8(3) no . . . .
C5 N1 N2 C14 150.3(3) no . . . .
N2 N1 C6 O6 176.0(3) no . . . .
N2 N1 C6 O7 -2.8(4) no . . . .
C6 N1 N2 C3 157.0(3) no . . . .
C6 N1 N2 C14 -59.6(4) no . . . .
C5 N1 C6 O6 -38.4(5) no . . . .
C5 N1 C6 O7 142.8(3) no . . . .
C6 N1 C5 C4 -153.4(3) no . . . .
C6 N1 C5 C21 25.0(5) no . . . .
N1 N2 C3 O3 172.5(3) no . . . .
N1 N2 C3 C4 -7.0(3) no . . . .
N1 N2 C14 C15 -20.0(5) no . . . .
N1 N2 C14 C19 159.7(3) no . . . .
C3 N2 C14 C15 118.2(3) no . . . .
C3 N2 C14 C19 -62.0(4) no . . . .
C14 N2 C3 O3 29.9(5) no . . . .
C14 N2 C3 C4 -149.6(3) no . . . .
O3 C3 C4 C5 -174.8(3) no . . . .
O3 C3 C4 C20 4.2(6) no . . . .
N2 C3 C4 C5 4.7(4) no . . . .
N2 C3 C4 C20 -176.3(3) no . . . .
C3 C4 C5 N1 -0.5(4) no . . . .
C3 C4 C5 C21 -178.7(3) no . . . .
C20 C4 C5 N1 -179.4(3) no . . . .
C20 C4 C5 C21 2.3(6) no . . . .
O7 C8 C9 C10 175.8(3) no . . . .
O7 C8 C13 C12 -176.1(3) no . . . .
C9 C8 C13 C12 -0.7(6) no . . . .
C13 C8 C9 C10 0.3(6) no . . . .
C8 C9 C10 C11 0.2(7) no . . . .
C9 C10 C11 C12 -0.4(7) no . . . .
C10 C11 C12 C13 0.1(6) no . . . .
C11 C12 C13 C8 0.5(6) no . . . .
N2 C14 C15 C16 179.1(3) no . . . .
N2 C14 C19 C18 178.3(3) no . . . .
C15 C14 C19 C18 -2.0(5) no . . . .
C19 C14 C15 C16 -0.7(5) no . . . .
C14 C15 C16 C17 3.0(5) no . . . .
C15 C16 C17 C18 -2.7(6) no . . . .
C16 C17 C18 C19 0.0(6) no . . . .
C17 C18 C19 C14 2.3(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O3 N1 3.451(4) no . .
O3 C5 3.468(5) no . .
O3 C14 2.906(5) no . .
O3 C19 3.001(5) no . .
O3 C20 3.054(5) no . .
O6 N2 3.550(4) no . .
O6 C5 2.921(5) no . .
O6 C8 2.696(5) no . .
O6 C9 3.588(5) no . .
O6 C13 3.109(5) no . .
O6 C21 2.856(5) no . .
O7 N2 2.608(4) no . .
O7 C5 3.516(4) no . .
O7 C14 2.823(4) no . .
O7 C15 3.069(4) no . .
N1 C8 3.555(5) no . .
N1 C15 2.882(5) no . .
C3 C6 3.575(5) no . .
C3 C15 3.556(5) no . .
C3 C19 3.093(5) no . .
C4 C6 3.542(5) no . .
C4 C14 3.594(5) no . .
C5 C14 3.570(5) no . .
C6 C9 3.344(5) no . .
C6 C13 3.007(5) no . .
C6 C14 3.083(5) no . .
C6 C15 3.212(5) no . .
C6 C21 3.013(5) no . .
C8 C11 2.740(6) no . .
C9 C12 2.775(6) no . .
C10 C13 2.753(6) no . .
C14 C17 2.770(6) no . .
C15 C18 2.777(6) no . .
C16 C19 2.770(6) no . .
C20 C21 3.208(7) no . .
O3 C13 3.449(5) no . 1_554
O3 C15 3.172(5) no . 1_554
O3 C16 3.432(5) no . 1_554
O6 C17 3.539(5) no . 11_464
O6 C18 3.378(5) no . 11_465
O6 C19 3.568(5) no . 11_465
O6 C20 3.482(5) no . 1_556
O7 C17 3.571(5) no . 11_464
C3 C13 3.508(5) no . 1_554
C6 C17 3.362(6) no . 11_464
C8 C21 3.396(5) no . 3_565
C10 C10 3.569(7) no . 12_665
C13 O3 3.449(5) no . 1_556
C13 C3 3.508(5) no . 1_556
C13 C21 3.493(6) no . 3_565
C15 O3 3.172(5) no . 1_556
C16 O3 3.432(5) no . 1_556
C17 O6 3.539(5) no . 3_565
C17 O7 3.571(5) no . 3_565
C17 C6 3.362(6) no . 3_565
C18 O6 3.378(5) no . 3_564
C19 O6 3.568(5) no . 3_564
C20 O6 3.482(5) no . 1_554
C21 C8 3.396(5) no . 11_464
C21 C13 3.493(6) no . 11_464
O3 H19 2.6706 no . .
O3 H20B 3.5810 no . .
O3 H20C 2.6926 no . .
O6 H13 3.0440 no . .
O6 H15 3.5165 no . .
O6 H21A 2.7020 no . .
O6 H21B 2.5689 no . .
O7 H9 2.5602 no . .
O7 H13 2.5821 no . .
O7 H15 3.0363 no . .
N1 H15 2.5953 no . .
N1 H21A 2.7637 no . .
N1 H21B 2.7943 no . .
N1 H21C 3.3207 no . .
N2 H15 2.6534 no . .
N2 H19 2.5826 no . .
C3 H19 2.9616 no . .
C3 H20A 3.2632 no . .
C3 H20B 3.1091 no . .
C3 H20C 2.6285 no . .
C4 H21A 3.1797 no . .
C4 H21B 3.1372 no . .
C4 H21C 2.6554 no . .
C5 H20A 2.7687 no . .
C5 H20B 2.9314 no . .
C5 H20C 3.3105 no . .
C6 H9 3.4877 no . .
C6 H13 2.9205 no . .
C6 H15 2.8402 no . .
C6 H21A 3.0910 no . .
C6 H21B 2.8843 no . .
C8 H10 3.2160 no . .
C8 H12 3.2414 no . .
C9 H11 3.2619 no . .
C9 H13 3.2493 no . .
C10 H12 3.2453 no . .
C11 H9 3.2666 no . .
C11 H13 3.2542 no . .
C12 H10 3.2406 no . .
C13 H9 3.2523 no . .
C13 H11 3.2546 no . .
C14 H16 3.2525 no . .
C14 H18 3.2479 no . .
C15 H13 3.2245 no . .
C15 H17 3.2645 no . .
C15 H19 3.2755 no . .
C16 H18 3.2550 no . .
C17 H15 3.2663 no . .
C17 H19 3.2562 no . .
C18 H16 3.2548 no . .
C19 H15 3.2773 no . .
C19 H17 3.2546 no . .
C20 H21C 2.8136 no . .
C21 H20A 3.0508 no . .
C21 H20B 3.3690 no . .
H9 H10 2.3369 no . .
H10 H11 2.3309 no . .
H11 H12 2.3265 no . .
H12 H13 2.3522 no . .
H13 H15 2.8859 no . .
H13 H16 3.5357 no . .
H15 H16 2.3348 no . .
H16 H17 2.3373 no . .
H17 H18 2.3387 no . .
H18 H19 2.3190 no . .
H20A H21A 3.5801 no . .
H20A H21C 2.4687 no . .
H20B H21C 2.8912 no . .
O3 H10 3.3691 no . 2_654
O3 H13 2.5118 no . 1_554
O3 H15 2.4440 no . 1_554
O3 H16 2.9592 no . 1_554
O3 H21A 3.4055 no . 16_664
O6 H16 3.3902 no . 11_464
O6 H17 3.2398 no . 11_464
O6 H18 2.6451 no . 11_465
O6 H19 3.0396 no . 11_465
O6 H20B 2.8144 no . 1_556
O6 H20C 3.5034 no . 1_556
O7 H12 2.9693 no . 1_554
O7 H17 2.7839 no . 11_464
O7 H21B 3.3197 no . 3_565
O7 H21C 3.3963 no . 3_565
N1 H17 3.4181 no . 11_464
N1 H20A 3.3872 no . 16_665
N1 H20C 3.4011 no . 16_665
N2 H12 3.0954 no . 1_554
N2 H13 3.0226 no . 1_554
N2 H20A 3.5540 no . 16_665
C3 H13 2.7093 no . 1_554
C3 H15 3.4841 no . 1_554
C3 H20C 3.3522 no . 16_665
C4 H20C 2.9476 no . 16_665
C5 H20C 2.9825 no . 16_665
C6 H17 2.8694 no . 11_464
C6 H18 3.5570 no . 11_465
C8 H17 3.3753 no . 11_464
C8 H18 3.1346 no . 11_465
C8 H21A 3.4882 no . 3_565
C8 H21B 3.0948 no . 3_565
C8 H21C 3.0587 no . 3_565
C9 H10 3.3468 no . 12_665
C9 H16 3.3060 no . 6_644
C9 H17 3.1957 no . 11_464
C9 H18 3.5552 no . 11_465
C9 H21A 3.5956 no . 3_565
C9 H21C 3.0445 no . 3_565
C10 H10 3.3382 no . 12_665
C10 H16 3.0857 no . 6_644
C10 H21A 3.5408 no . 3_565
C10 H21C 3.5021 no . 3_565
C11 H17 3.5035 no . 11_465
C11 H18 3.5141 no . 11_465
C11 H20B 3.5794 no . 3_566
C11 H21A 3.4066 no . 3_565
C12 H17 3.2824 no . 11_465
C12 H18 3.1042 no . 11_465
C12 H19 3.1639 no . 1_556
C12 H20B 3.3198 no . 3_566
C12 H21A 3.3051 no . 3_565
C13 H18 2.8988 no . 11_465
C13 H19 3.0802 no . 1_556
C13 H21A 3.3469 no . 3_565
C13 H21B 3.0437 no . 3_565
C13 H21C 3.5311 no . 3_565
C14 H11 3.2931 no . 2_654
C14 H12 3.3457 no . 1_554
C14 H20A 3.5453 no . 16_665
C14 H21B 3.5782 no . 3_565
C15 H11 3.0851 no . 2_654
C15 H20A 3.0428 no . 16_665
C15 H21B 3.3684 no . 3_565
C16 H9 3.3997 no . 2_655
C16 H10 3.3609 no . 2_655
C16 H11 2.9676 no . 2_654
C16 H21B 3.0486 no . 3_565
C17 H9 3.3998 no . 3_565
C17 H11 3.0214 no . 2_654
C17 H21B 3.0234 no . 3_565
C18 H10 2.9656 no . 2_654
C18 H11 3.2304 no . 2_654
C18 H21B 3.2662 no . 3_565
C19 H10 3.0289 no . 2_654
C19 H11 3.3836 no . 2_654
C19 H12 3.1171 no . 1_554
C19 H13 3.3171 no . 1_554
C19 H21B 3.5171 no . 3_565
C20 H15 3.4741 no . 16_664
C20 H20C 3.4616 no . 16_665
C20 H21A 3.3592 no . 1_554
C21 H20B 3.5884 no . 1_556
C21 H20C 3.5618 no . 16_665
H9 C16 3.3997 no . 6_644
H9 C17 3.3998 no . 11_464
H9 H9 3.1519 no . 12_665
H9 H10 3.3774 no . 12_665
H9 H11 3.2291 no . 1_554
H9 H12 3.3871 no . 1_554
H9 H16 2.8981 no . 6_644
H9 H16 3.5119 no . 11_464
H9 H17 2.5547 no . 11_464
H9 H21C 3.2630 no . 3_565
H10 O3 3.3691 no . 6_645
H10 C9 3.3468 no . 12_665
H10 C10 3.3382 no . 12_665
H10 C16 3.3609 no . 6_644
H10 C18 2.9656 no . 6_645
H10 C19 3.0289 no . 6_645
H10 H9 3.3774 no . 12_665
H10 H10 3.3599 no . 12_665
H10 H16 2.4339 no . 6_644
H10 H18 2.9877 no . 6_645
H10 H19 3.1261 no . 6_645
H11 C14 3.2931 no . 6_645
H11 C15 3.0851 no . 6_645
H11 C16 2.9676 no . 6_645
H11 C17 3.0214 no . 6_645
H11 C18 3.2304 no . 6_645
H11 C19 3.3836 no . 6_645
H11 H9 3.2291 no . 1_556
H11 H15 3.5519 no . 6_645
H11 H16 3.4134 no . 6_645
H11 H17 3.4612 no . 6_645
H11 H17 3.5304 no . 11_465
H11 H20A 3.3432 no . 3_566
H11 H20B 3.4903 no . 3_566
H12 O7 2.9693 no . 1_556
H12 N2 3.0954 no . 1_556
H12 C14 3.3457 no . 1_556
H12 C19 3.1171 no . 1_556
H12 H9 3.3871 no . 1_556
H12 H17 3.1500 no . 11_465
H12 H18 3.4823 no . 11_465
H12 H19 2.6838 no . 1_556
H12 H20B 3.0235 no . 3_566
H12 H21C 3.3678 no . 3_566
H13 O3 2.5118 no . 1_556
H13 N2 3.0226 no . 1_556
H13 C3 2.7093 no . 1_556
H13 C19 3.3171 no . 1_556
H13 H18 3.1773 no . 11_465
H13 H19 2.5165 no . 1_556
H13 H21B 3.1525 no . 3_565
H15 O3 2.4440 no . 1_556
H15 C3 3.4841 no . 1_556
H15 C20 3.4741 no . 16_665
H15 H11 3.5519 no . 2_654
H15 H20A 2.5317 no . 16_665
H15 H20C 3.4520 no . 1_556
H16 O3 2.9592 no . 1_556
H16 O6 3.3902 no . 3_565
H16 C9 3.3060 no . 2_655
H16 C10 3.0857 no . 2_655
H16 H9 2.8981 no . 2_655
H16 H9 3.5119 no . 3_565
H16 H10 2.4339 no . 2_655
H16 H11 3.4134 no . 2_654
H16 H19 3.0249 no . 1_556
H16 H21B 3.3972 no . 3_565
H17 O6 3.2398 no . 3_565
H17 O7 2.7839 no . 3_565
H17 N1 3.4181 no . 3_565
H17 C6 2.8694 no . 3_565
H17 C8 3.3753 no . 3_565
H17 C9 3.1957 no . 3_565
H17 C11 3.5035 no . 3_564
H17 C12 3.2824 no . 3_564
H17 H9 2.5547 no . 3_565
H17 H11 3.4612 no . 2_654
H17 H11 3.5304 no . 3_564
H17 H12 3.1500 no . 3_564
H17 H21B 3.3938 no . 3_565
H18 O6 2.6451 no . 3_564
H18 C6 3.5570 no . 3_564
H18 C8 3.1346 no . 3_564
H18 C9 3.5552 no . 3_564
H18 C11 3.5141 no . 3_564
H18 C12 3.1042 no . 3_564
H18 C13 2.8988 no . 3_564
H18 H10 2.9877 no . 2_654
H18 H12 3.4823 no . 3_564
H18 H13 3.1773 no . 3_564
H18 H20B 3.5417 no . 3_565
H19 O6 3.0396 no . 3_564
H19 C12 3.1639 no . 1_554
H19 C13 3.0802 no . 1_554
H19 H10 3.1261 no . 2_654
H19 H12 2.6838 no . 1_554
H19 H13 2.5165 no . 1_554
H19 H16 3.0249 no . 1_554
H19 H20B 3.4684 no . 3_565
H20A N1 3.3872 no . 16_664
H20A N2 3.5540 no . 16_664
H20A C14 3.5453 no . 16_664
H20A C15 3.0428 no . 16_664
H20A H11 3.3432 no . 11_463
H20A H15 2.5317 no . 16_664
H20A H20C 3.1297 no . 16_665
H20B O6 2.8144 no . 1_554
H20B C11 3.5794 no . 11_463
H20B C12 3.3198 no . 11_463
H20B C21 3.5884 no . 1_554
H20B H11 3.4903 no . 11_463
H20B H12 3.0235 no . 11_463
H20B H18 3.5417 no . 11_464
H20B H19 3.4684 no . 11_464
H20B H21A 2.6995 no . 1_554
H20C O6 3.5034 no . 1_554
H20C N1 3.4011 no . 16_664
H20C C3 3.3522 no . 16_664
H20C C4 2.9476 no . 16_664
H20C C5 2.9825 no . 16_664
H20C C20 3.4616 no . 16_664
H20C C21 3.5618 no . 16_664
H20C H15 3.4520 no . 1_554
H20C H20A 3.1297 no . 16_664
H20C H21A 3.1755 no . 1_554
H20C H21A 3.3367 no . 16_664
H21A O3 3.4055 no . 16_665
H21A C8 3.4882 no . 11_464
H21A C9 3.5956 no . 11_464
H21A C10 3.5408 no . 11_464
H21A C11 3.4066 no . 11_464
H21A C12 3.3051 no . 11_464
H21A C13 3.3469 no . 11_464
H21A C20 3.3592 no . 1_556
H21A H20B 2.6995 no . 1_556
H21A H20C 3.1755 no . 1_556
H21A H20C 3.3367 no . 16_665
H21B O7 3.3197 no . 11_464
H21B C8 3.0948 no . 11_464
H21B C13 3.0437 no . 11_464
H21B C14 3.5782 no . 11_464
H21B C15 3.3684 no . 11_464
H21B C16 3.0486 no . 11_464
H21B C17 3.0234 no . 11_464
H21B C18 3.2662 no . 11_464
H21B C19 3.5171 no . 11_464
H21B H13 3.1525 no . 11_464
H21B H16 3.3972 no . 11_464
H21B H17 3.3938 no . 11_464
H21C O7 3.3963 no . 11_464
H21C C8 3.0587 no . 11_464
H21C C9 3.0445 no . 11_464
H21C C10 3.5021 no . 11_464
H21C C13 3.5311 no . 11_464
H21C H9 3.2630 no . 11_464
H21C H12 3.3678 no . 11_463

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 987861'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_29


_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_weight         246.27
_chemical_melting_point          ?
_chemical_absolute_configuration ad

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.2771(10)
_cell_length_b                   11.7706(18)
_cell_length_c                   8.7028(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.826(5)
_cell_angle_gamma                90.0000
_cell_volume                     637.02(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4591
_cell_measurement_theta_min      5.13
_cell_measurement_theta_max      67.72
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             260.00
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            7964
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_theta_max         67.71
_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2187
_reflns_number_gt                2098
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1307
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2187
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0358P)²+0.4217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.005
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O3 O 0.6791(4) 0.4599(2) 0.9985(3) 0.0437(7) Uani 1.0 2 d . . .
O7 O 0.9952(5) 0.3306(3) 0.6759(3) 0.0535(8) Uani 1.0 2 d . . .
O8 O 0.7884(4) 0.23190(19) 0.8184(3) 0.0366(6) Uani 1.0 2 d . . .
N1 N 1.0617(5) 0.2758(3) 1.1874(3) 0.0366(7) Uani 1.0 2 d . . .
N2 N 0.8765(5) 0.3437(3) 1.1765(3) 0.0375(7) Uani 1.0 2 d . . .
C3 C 0.8318(6) 0.3992(3) 1.0393(4) 0.0317(8) Uani 1.0 2 d . . .
C4 C 1.0180(5) 0.3700(3) 0.9493(4) 0.0287(7) Uani 1.0 2 d . . .
C5 C 1.1433(5) 0.2873(3) 1.0609(4) 0.0303(7) Uani 1.0 2 d . . .
C6 C 0.7533(7) 0.3470(4) 1.3052(4) 0.0513(10) Uani 1.0 2 d . . .
C7 C 0.9355(5) 0.3117(3) 0.7970(4) 0.0296(7) Uani 1.0 2 d . . .
C9 C 0.6930(6) 0.1717(3) 0.6861(4) 0.0308(7) Uani 1.0 2 d . . .
C10 C 0.4889(6) 0.2014(3) 0.6214(4) 0.0379(8) Uani 1.0 2 d . . .
C11 C 0.3922(6) 0.1394(4) 0.4960(4) 0.0427(9) Uani 1.0 2 d . . .
C12 C 0.4986(7) 0.0500(4) 0.4383(5) 0.0482(10) Uani 1.0 2 d . . .
C13 C 0.7020(7) 0.0208(4) 0.5059(5) 0.0487(10) Uani 1.0 2 d . . .
C14 C 0.8013(6) 0.0826(4) 0.6318(5) 0.0406(8) Uani 1.0 2 d . . .
C15 C 1.1450(6) 0.4771(3) 0.9220(4) 0.0364(8) Uani 1.0 2 d . . .
C16 C 1.3385(6) 0.2262(3) 1.0285(4) 0.0404(9) Uani 1.0 2 d . . .
H6A H 0.6885 0.2724 1.3174 0.0616 Uiso 1.0 2 calc R . .
H6B H 0.6395 0.4043 1.2850 0.0616 Uiso 1.0 2 calc R . .
H6C H 0.8482 0.3667 1.4004 0.0616 Uiso 1.0 2 calc R . .
H10 H 0.4160 0.2630 0.6618 0.0455 Uiso 1.0 2 calc R . .
H11 H 0.2511 0.1587 0.4492 0.0513 Uiso 1.0 2 calc R . .
H12 H 0.4312 0.0084 0.3514 0.0578 Uiso 1.0 2 calc R . .
H13 H 0.7744 -0.0415 0.4667 0.0584 Uiso 1.0 2 calc R . .
H14 H 0.9420 0.0634 0.6793 0.0487 Uiso 1.0 2 calc R . .
H15A H 1.1946 0.5136 1.0216 0.0437 Uiso 1.0 2 calc R . .
H15B H 1.0526 0.5298 0.8559 0.0437 Uiso 1.0 2 calc R . .
H15C H 1.2694 0.4567 0.8708 0.0437 Uiso 1.0 2 calc R . .
H16A H 1.4009 0.1847 1.1215 0.0485 Uiso 1.0 2 calc R . .
H16B H 1.4436 0.2810 0.9995 0.0485 Uiso 1.0 2 calc R . .
H16C H 1.3002 0.1725 0.9432 0.0485 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O3 C3 1.209(4) yes . .
O7 C7 1.187(5) yes . .
O8 C7 1.348(4) yes . .
O8 C9 1.414(4) yes . .
N1 N2 1.404(5) yes . .
N1 C5 1.283(5) yes . .
N2 C3 1.356(5) yes . .
N2 C6 1.446(5) yes . .
C3 C4 1.532(5) yes . .
C4 C5 1.518(5) yes . .
C4 C7 1.520(5) yes . .
C4 C15 1.527(5) yes . .
C5 C16 1.481(5) yes . .
C9 C10 1.373(5) yes . .
C9 C14 1.368(5) yes . .
C10 C11 1.383(5) yes . .
C11 C12 1.378(6) yes . .
C12 C13 1.375(6) yes . .
C13 C14 1.390(6) yes . .
C6 H6A 0.980 no . .
C6 H6B 0.980 no . .
C6 H6C 0.980 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .
C16 H16A 0.980 no . .
C16 H16B 0.980 no . .
C16 H16C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C7 O8 C9 117.3(3) yes . . .
N2 N1 C5 107.8(3) yes . . .
N1 N2 C3 113.8(3) yes . . .
N1 N2 C6 119.3(3) yes . . .
C3 N2 C6 126.9(3) yes . . .
O3 C3 N2 127.1(4) yes . . .
O3 C3 C4 127.7(3) yes . . .
N2 C3 C4 105.2(3) yes . . .
C3 C4 C5 100.4(3) yes . . .
C3 C4 C7 110.7(3) yes . . .
C3 C4 C15 110.2(3) yes . . .
C5 C4 C7 110.7(3) yes . . .
C5 C4 C15 113.2(3) yes . . .
C7 C4 C15 111.1(3) yes . . .
N1 C5 C4 112.6(3) yes . . .
N1 C5 C16 123.3(3) yes . . .
C4 C5 C16 124.0(3) yes . . .
O7 C7 O8 124.0(3) yes . . .
O7 C7 C4 125.3(3) yes . . .
O8 C7 C4 110.7(3) yes . . .
O8 C9 C10 118.3(3) yes . . .
O8 C9 C14 119.4(3) yes . . .
C10 C9 C14 122.2(3) yes . . .
C9 C10 C11 118.3(4) yes . . .
C10 C11 C12 120.5(4) yes . . .
C11 C12 C13 120.2(4) yes . . .
C12 C13 C14 119.8(4) yes . . .
C9 C14 C13 118.9(4) yes . . .
N2 C6 H6A 109.467 no . . .
N2 C6 H6B 109.476 no . . .
N2 C6 H6C 109.471 no . . .
H6A C6 H6B 109.468 no . . .
H6A C6 H6C 109.469 no . . .
H6B C6 H6C 109.477 no . . .
C9 C10 H10 120.836 no . . .
C11 C10 H10 120.834 no . . .
C10 C11 H11 119.732 no . . .
C12 C11 H11 119.736 no . . .
C11 C12 H12 119.882 no . . .
C13 C12 H12 119.881 no . . .
C12 C13 H13 120.113 no . . .
C14 C13 H13 120.107 no . . .
C9 C14 H14 120.560 no . . .
C13 C14 H14 120.560 no . . .
C4 C15 H15A 109.468 no . . .
C4 C15 H15B 109.471 no . . .
C4 C15 H15C 109.471 no . . .
H15A C15 H15B 109.474 no . . .
H15A C15 H15C 109.469 no . . .
H15B C15 H15C 109.473 no . . .
C5 C16 H16A 109.470 no . . .
C5 C16 H16B 109.476 no . . .
C5 C16 H16C 109.473 no . . .
H16A C16 H16B 109.473 no . . .
H16A C16 H16C 109.462 no . . .
H16B C16 H16C 109.473 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C7 O8 C9 C10 -102.3(4) no . . . .
C7 O8 C9 C14 81.0(4) no . . . .
C9 O8 C7 O7 -3.3(5) no . . . .
C9 O8 C7 C4 178.7(3) no . . . .
N2 N1 C5 C4 1.4(4) no . . . .
N2 N1 C5 C16 -178.6(3) no . . . .
C5 N1 N2 C3 1.4(4) no . . . .
C5 N1 N2 C6 -179.6(3) no . . . .
N1 N2 C3 O3 177.5(3) no . . . .
N1 N2 C3 C4 -3.5(4) no . . . .
C6 N2 C3 O3 -1.4(6) no . . . .
C6 N2 C3 C4 177.6(3) no . . . .
O3 C3 C4 C5 -177.2(3) no . . . .
O3 C3 C4 C7 -60.2(4) no . . . .
O3 C3 C4 C15 63.2(4) no . . . .
N2 C3 C4 C5 3.8(3) no . . . .
N2 C3 C4 C7 120.8(3) no . . . .
N2 C3 C4 C15 -115.8(3) no . . . .
C3 C4 C5 N1 -3.3(3) no . . . .
C3 C4 C5 C16 176.7(3) no . . . .
C3 C4 C7 O7 137.5(3) no . . . .
C3 C4 C7 O8 -44.5(4) no . . . .
C5 C4 C7 O7 -112.0(4) no . . . .
C5 C4 C7 O8 66.0(4) no . . . .
C7 C4 C5 N1 -120.3(3) no . . . .
C7 C4 C5 C16 59.7(4) no . . . .
C15 C4 C5 N1 114.2(3) no . . . .
C15 C4 C5 C16 -65.8(4) no . . . .
C15 C4 C7 O7 14.7(5) no . . . .
C15 C4 C7 O8 -167.3(3) no . . . .
O8 C9 C10 C11 -177.4(3) no . . . .
O8 C9 C14 C13 177.1(3) no . . . .
C10 C9 C14 C13 0.6(6) no . . . .
C14 C9 C10 C11 -0.8(6) no . . . .
C9 C10 C11 C12 0.2(6) no . . . .
C10 C11 C12 C13 0.6(6) no . . . .
C11 C12 C13 C14 -0.8(6) no . . . .
C12 C13 C14 C9 0.2(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O3 O8 3.228(4) no . .
O3 N1 3.477(4) no . .
O3 C5 3.533(4) no . .
O3 C6 2.961(5) no . .
O3 C7 3.078(5) no . .
O3 C15 3.093(5) no . .
O7 C3 3.548(5) no . .
O7 C5 3.392(4) no . .
O7 C9 2.675(5) no . .
O7 C10 3.497(5) no . .
O7 C14 3.166(5) no . .
O7 C15 2.810(5) no . .
O8 N1 3.467(4) no . .
O8 N2 3.359(4) no . .
O8 C3 2.739(4) no . .
O8 C5 2.926(4) no . .
N1 C7 3.408(4) no . .
N1 C15 3.399(5) no . .
N2 C7 3.394(5) no . .
N2 C15 3.351(5) no . .
C5 C6 3.525(6) no . .
C7 C10 3.273(5) no . .
C7 C14 3.117(5) no . .
C7 C16 3.176(5) no . .
C9 C12 2.734(5) no . .
C10 C13 2.772(6) no . .
C11 C14 2.759(5) no . .
C15 C16 3.279(5) no . .
O3 C15 3.334(5) no . 1_455
O3 C16 3.515(5) no . 1_455
O3 C16 3.144(5) no . 2_757
O7 C6 3.379(5) no . 1_554
O7 C10 3.542(5) no . 1_655
O7 C13 3.456(6) no . 2_756
O8 C16 3.568(5) no . 1_455
N1 C11 3.546(5) no . 1_656
C6 O7 3.379(5) no . 1_556
C6 C16 3.590(5) no . 1_455
C10 O7 3.542(5) no . 1_455
C11 N1 3.546(5) no . 1_454
C13 O7 3.456(6) no . 2_746
C15 O3 3.334(5) no . 1_655
C16 O3 3.515(5) no . 1_655
C16 O3 3.144(5) no . 2_747
C16 O8 3.568(5) no . 1_655
C16 C6 3.590(5) no . 1_655
O3 H6A 3.5401 no . .
O3 H6B 2.6223 no . .
O3 H15A 3.2761 no . .
O3 H15B 2.9162 no . .
O7 H14 3.1641 no . .
O7 H15B 2.8152 no . .
O7 H15C 2.6917 no . .
O7 H16C 3.3649 no . .
O8 H10 2.5668 no . .
O8 H14 2.5787 no . .
O8 H16C 3.3222 no . .
N1 H6A 2.7369 no . .
N1 H6B 3.2627 no . .
N1 H6C 2.6559 no . .
N1 H15A 3.3079 no . .
N1 H16A 2.5191 no . .
N1 H16B 3.0809 no . .
N1 H16C 3.0170 no . .
N2 H15A 3.2458 no . .
C3 H6A 3.0799 no . .
C3 H6B 2.5951 no . .
C3 H6C 3.1531 no . .
C3 H15A 2.6683 no . .
C3 H15B 2.7265 no . .
C3 H15C 3.3544 no . .
C4 H16A 3.4355 no . .
C4 H16B 2.8477 no . .
C4 H16C 2.9276 no . .
C5 H15A 2.7107 no . .
C5 H15B 3.3731 no . .
C5 H15C 2.7745 no . .
C7 H10 3.3617 no . .
C7 H14 3.0995 no . .
C7 H15A 3.3543 no . .
C7 H15B 2.7001 no . .
C7 H15C 2.7116 no . .
C7 H16B 3.4469 no . .
C7 H16C 2.9578 no . .
C9 H11 3.2264 no . .
C9 H13 3.2355 no . .
C10 H12 3.2523 no . .
C10 H14 3.2544 no . .
C11 H13 3.2445 no . .
C12 H10 3.2574 no . .
C12 H14 3.2526 no . .
C13 H11 3.2418 no . .
C14 H10 3.2554 no . .
C14 H12 3.2507 no . .
C15 H16B 2.9924 no . .
C16 H15A 3.4999 no . .
C16 H15C 3.0447 no . .
H10 H11 2.3406 no . .
H11 H12 2.3222 no . .
H12 H13 2.3249 no . .
H13 H14 2.3498 no . .
H14 H16C 3.2517 no . .
H15A H16B 3.1718 no . .
H15C H16B 2.5287 no . .
H15C H16C 3.4041 no . .
O3 H12 3.0832 no . 2_656
O3 H15A 3.1397 no . 1_455
O3 H15C 2.6595 no . 1_455
O3 H16A 2.8635 no . 2_757
O3 H16B 2.5734 no . 1_455
O3 H16C 2.5538 no . 2_757
O7 H6A 3.5036 no . 1_554
O7 H6C 2.4860 no . 1_554
O7 H10 2.7773 no . 1_655
O7 H11 3.3810 no . 1_655
O7 H12 3.3808 no . 2_656
O7 H13 2.5272 no . 2_756
O8 H15A 2.9170 no . 2_747
O8 H16B 2.9032 no . 1_455
O8 H16C 3.4589 no . 1_455
N1 H11 2.7867 no . 1_656
N1 H14 3.5792 no . 2_757
N1 H15B 2.9946 no . 2_747
N2 H14 3.0276 no . 2_757
N2 H16A 3.5012 no . 1_455
N2 H16B 3.0269 no . 1_455
C3 H14 3.2863 no . 2_757
C3 H16B 2.7862 no . 1_455
C3 H16C 3.3311 no . 2_757
C5 H15B 3.3860 no . 2_747
C6 H13 3.5843 no . 2_757
C6 H14 3.1765 no . 2_757
C6 H16A 3.1841 no . 1_455
C6 H16B 3.1703 no . 1_455
C7 H6C 3.4813 no . 1_554
C7 H10 3.4319 no . 1_655
C7 H12 3.3942 no . 2_656
C7 H13 3.5649 no . 2_756
C9 H6A 3.4176 no . 1_554
C9 H15A 3.1523 no . 2_747
C9 H16B 3.5647 no . 1_455
C9 H16C 3.5477 no . 1_455
C10 H6A 3.1892 no . 1_554
C10 H13 3.4834 no . 2_656
C10 H16B 3.4700 no . 1_455
C10 H16C 3.2036 no . 1_455
C11 H6A 3.0186 no . 1_554
C11 H6B 3.3820 no . 2_647
C11 H14 3.5442 no . 1_455
C11 H16A 3.3105 no . 1_454
C12 H6A 3.1175 no . 1_554
C12 H6B 3.1723 no . 2_647
C12 H6C 3.4928 no . 2_647
C12 H10 3.5481 no . 2_646
C12 H15C 3.4100 no . 2_746
C12 H16A 3.1669 no . 1_454
C13 H6A 3.3812 no . 1_554
C13 H6B 3.2939 no . 2_647
C13 H6C 3.3615 no . 2_747
C13 H10 3.4045 no . 2_646
C13 H15C 3.3923 no . 2_746
C14 H6A 3.5285 no . 1_554
C14 H6C 3.3980 no . 2_747
C14 H11 3.5388 no . 1_655
C14 H15A 3.1201 no . 2_747
C15 H13 3.4945 no . 2_756
C16 H6A 3.1527 no . 1_655
C16 H6B 3.4348 no . 1_655
C16 H10 3.3215 no . 1_655
H6A O7 3.5036 no . 1_556
H6A C9 3.4176 no . 1_556
H6A C10 3.1892 no . 1_556
H6A C11 3.0186 no . 1_556
H6A C12 3.1175 no . 1_556
H6A C13 3.3812 no . 1_556
H6A C14 3.5285 no . 1_556
H6A C16 3.1527 no . 1_455
H6A H11 3.3915 no . 1_556
H6A H12 3.5325 no . 1_556
H6A H16A 2.5289 no . 1_455
H6A H16B 2.9781 no . 1_455
H6B C11 3.3820 no . 2_657
H6B C12 3.1723 no . 2_657
H6B C13 3.2939 no . 2_657
H6B C16 3.4348 no . 1_455
H6B H12 3.4776 no . 2_657
H6B H14 3.2064 no . 2_757
H6B H16A 3.2205 no . 1_455
H6B H16B 2.9933 no . 1_455
H6C O7 2.4860 no . 1_556
H6C C7 3.4813 no . 1_556
H6C C12 3.4928 no . 2_657
H6C C13 3.3615 no . 2_757
H6C C14 3.3980 no . 2_757
H6C H11 3.5041 no . 1_656
H6C H12 3.3995 no . 2_657
H6C H13 2.7148 no . 2_757
H6C H14 2.7970 no . 2_757
H10 O7 2.7773 no . 1_455
H10 C7 3.4319 no . 1_455
H10 C12 3.5481 no . 2_656
H10 C13 3.4045 no . 2_656
H10 C16 3.3215 no . 1_455
H10 H12 3.0513 no . 2_656
H10 H13 2.7589 no . 2_656
H10 H15C 3.1319 no . 1_455
H10 H16B 2.9281 no . 1_455
H10 H16C 2.8534 no . 1_455
H11 O7 3.3810 no . 1_455
H11 N1 2.7867 no . 1_454
H11 C14 3.5388 no . 1_455
H11 H6A 3.3915 no . 1_554
H11 H6C 3.5041 no . 1_454
H11 H14 3.1772 no . 1_455
H11 H15B 3.4074 no . 2_646
H11 H16A 3.1375 no . 1_454
H12 O3 3.0832 no . 2_646
H12 O7 3.3808 no . 2_646
H12 C7 3.3942 no . 2_646
H12 H6A 3.5325 no . 1_554
H12 H6B 3.4776 no . 2_647
H12 H6C 3.3995 no . 2_647
H12 H10 3.0513 no . 2_646
H12 H15B 3.3242 no . 2_646
H12 H15C 2.9380 no . 2_746
H12 H16A 2.8707 no . 1_454
H13 O7 2.5272 no . 2_746
H13 C6 3.5843 no . 2_747
H13 C7 3.5649 no . 2_746
H13 C10 3.4834 no . 2_646
H13 C15 3.4945 no . 2_746
H13 H6C 2.7148 no . 2_747
H13 H10 2.7589 no . 2_646
H13 H15B 3.2553 no . 2_746
H13 H15C 2.9127 no . 2_746
H14 N1 3.5792 no . 2_747
H14 N2 3.0276 no . 2_747
H14 C3 3.2863 no . 2_747
H14 C6 3.1765 no . 2_747
H14 C11 3.5442 no . 1_655
H14 H6B 3.2064 no . 2_747
H14 H6C 2.7970 no . 2_747
H14 H11 3.1772 no . 1_655
H14 H15A 2.9084 no . 2_747
H15A O3 3.1397 no . 1_655
H15A O8 2.9170 no . 2_757
H15A C9 3.1523 no . 2_757
H15A C14 3.1201 no . 2_757
H15A H14 2.9084 no . 2_757
H15A H16A 3.5932 no . 2_857
H15B N1 2.9946 no . 2_757
H15B C5 3.3860 no . 2_757
H15B H11 3.4074 no . 2_656
H15B H12 3.3242 no . 2_656
H15B H13 3.2553 no . 2_756
H15B H16A 3.4086 no . 2_757
H15B H16C 3.4407 no . 2_757
H15C O3 2.6595 no . 1_655
H15C C12 3.4100 no . 2_756
H15C C13 3.3923 no . 2_756
H15C H10 3.1319 no . 1_655
H15C H12 2.9380 no . 2_756
H15C H13 2.9127 no . 2_756
H15C H16A 3.3837 no . 2_857
H16A O3 2.8635 no . 2_747
H16A N2 3.5012 no . 1_655
H16A C6 3.1841 no . 1_655
H16A C11 3.3105 no . 1_656
H16A C12 3.1669 no . 1_656
H16A H6A 2.5289 no . 1_655
H16A H6B 3.2205 no . 1_655
H16A H11 3.1375 no . 1_656
H16A H12 2.8707 no . 1_656
H16A H15A 3.5932 no . 2_847
H16A H15B 3.4086 no . 2_747
H16A H15C 3.3837 no . 2_847
H16B O3 2.5734 no . 1_655
H16B O8 2.9032 no . 1_655
H16B N2 3.0269 no . 1_655
H16B C3 2.7862 no . 1_655
H16B C6 3.1703 no . 1_655
H16B C9 3.5647 no . 1_655
H16B C10 3.4700 no . 1_655
H16B H6A 2.9781 no . 1_655
H16B H6B 2.9933 no . 1_655
H16B H10 2.9281 no . 1_655
H16C O3 2.5538 no . 2_747
H16C O8 3.4589 no . 1_655
H16C C3 3.3311 no . 2_747
H16C C9 3.5477 no . 1_655
H16C C10 3.2036 no . 1_655
H16C H10 2.8534 no . 1_655
H16C H15B 3.4407 no . 2_747

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 987862'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S13

_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_weight         308.34
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,+Y,1/2+Z
3 1/2+X,-Y,+Z
4 -X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   28.940(9)
_cell_length_b                   5.9109(15)
_cell_length_c                   9.179(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1570.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5032
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648.00
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.982

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            8362
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_max         25.360
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.768
_diffrn_reflns_point_group_measured_fraction_full 0.780
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2204
_reflns_number_gt                2111
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0859
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     210
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0511P)²+0.0826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.1(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.70494(5) 0.1088(2) 0.35155(18) 0.0295(4) Uani 1 4 0 d . . .
O7 O 0.74183(6) 0.3500(3) 0.1981(2) 0.0391(5) Uani 1 4 0 d . . .
O8 O 0.77873(6) 0.1043(3) 0.3477(2) 0.0313(4) Uani 1 4 0 d . . .
N1 N 0.59916(7) 0.3821(3) 0.2826(2) 0.0251(5) Uani 1 4 0 d . . .
N2 N 0.64091(6) 0.3589(3) 0.3470(2) 0.0254(5) Uani 1 4 0 d . . .
C3 C 0.66257(8) 0.1743(4) 0.2959(3) 0.0245(5) Uani 1 4 0 d . . .
C4 C 0.63586(8) 0.0656(4) 0.1957(3) 0.0249(5) Uani 1 4 0 d . . .
C5 C 0.59567(8) 0.2048(4) 0.1905(3) 0.0227(5) Uani 1 4 0 d . . .
C6 C 0.65785(9) 0.5283(4) 0.4482(3) 0.0313(6) Uani 1 4 0 d . . .
C7 C 0.74248(8) 0.2054(4) 0.2881(3) 0.0261(5) Uani 1 4 0 d . . .
C9 C 0.82282(8) 0.1757(4) 0.2992(3) 0.0264(5) Uani 1 4 0 d . . .
C10 C 0.84205(9) 0.3675(4) 0.3566(3) 0.0325(6) Uani 1 4 0 d . . .
C11 C 0.88662(10) 0.4222(5) 0.3175(3) 0.0400(7) Uani 1 4 0 d . . .
C12 C 0.91129(9) 0.2828(5) 0.2241(3) 0.0438(7) Uani 1 4 0 d . . .
C13 C 0.89089(10) 0.0914(5) 0.1677(3) 0.0449(7) Uani 1 4 0 d . . .
C14 C 0.84597(9) 0.0362(4) 0.2049(3) 0.0344(6) Uani 1 4 0 d . . .
C15 C 0.64931(9) -0.1424(3) 0.1124(3) 0.0304(6) Uani 1 4 0 d . . .
C16 C 0.55418(8) 0.1850(3) 0.0983(3) 0.0233(5) Uani 1 4 0 d . . .
C17 C 0.54393(9) -0.0132(4) 0.0219(3) 0.0288(6) Uani 1 4 0 d . . .
C18 C 0.50621(9) -0.0249(4) -0.0702(3) 0.0316(6) Uani 1 4 0 d . . .
C19 C 0.47736(9) 0.1596(4) -0.0870(3) 0.0301(6) Uani 1 4 0 d . . .
C20 C 0.48630(8) 0.3561(4) -0.0092(3) 0.0299(6) Uani 1 4 0 d . . .
C21 C 0.52394(8) 0.3687(4) 0.0825(3) 0.0267(6) Uani 1 4 0 d . . .
H6A H 0.67635 0.64021 0.39534 0.0376 Uiso 1 4 0 calc R . .
H6B H 0.67701 0.45522 0.52263 0.0376 Uiso 1 4 0 calc R . .
H6C H 0.63161 0.60374 0.49507 0.0376 Uiso 1 4 0 calc R . .
H10 H 0.82508 0.46068 0.42176 0.0389 Uiso 1 4 0 calc R . .
H11 H 0.90052 0.55591 0.3547 0.0480 Uiso 1 4 0 calc R . .
H12 H 0.94225 0.31929 0.19899 0.0526 Uiso 1 4 0 calc R . .
H13 H 0.90772 -0.00306 0.10292 0.0539 Uiso 1 4 0 calc R . .
H14 H 0.83154 -0.095 0.16611 0.0413 Uiso 1 4 0 calc R . .
H15A H 0.63041 -0.27048 0.14476 0.0365 Uiso 1 4 0 calc R . .
H15B H 0.68201 -0.17598 0.12973 0.0365 Uiso 1 4 0 calc R . .
H15C H 0.64429 -0.1168 0.00805 0.0365 Uiso 1 4 0 calc R . .
H17 H 0.5632 -0.14208 0.03351 0.0346 Uiso 1 4 0 calc R . .
H18 H 0.50009 -0.16053 -0.12232 0.0379 Uiso 1 4 0 calc R . .
H19 H 0.45164 0.15194 -0.15113 0.0362 Uiso 1 4 0 calc R . .
H20 H 0.46635 0.48277 -0.01929 0.0359 Uiso 1 4 0 calc R . .
H21 H 0.52947 0.50387 0.13572 0.0320 Uiso 1 4 0 calc R . .



#==============================================================================
_computing_data_collection       
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O3 C3 1.383(3) yes . .
O3 C7 1.359(3) yes . .
O7 C7 1.189(3) yes . .
O8 C7 1.325(3) yes . .
O8 C9 1.415(3) yes . .
N1 N2 1.352(3) yes . .
N1 C5 1.350(3) yes . .
N2 C3 1.343(3) yes . .
N2 C6 1.451(3) yes . .
C3 C4 1.363(3) yes . .
C4 C5 1.426(3) yes . .
C4 C15 1.500(3) yes . .
C5 C16 1.474(3) yes . .
C9 C10 1.368(3) yes . .
C9 C14 1.371(4) yes . .
C10 C11 1.377(4) yes . .
C11 C12 1.388(4) yes . .
C12 C13 1.377(4) yes . .
C13 C14 1.383(4) yes . .
C16 C17 1.397(3) yes . .
C16 C21 1.402(3) yes . .
C17 C18 1.383(4) yes . .
C18 C19 1.382(3) yes . .
C19 C20 1.388(3) yes . .
C20 C21 1.379(3) yes . .
C6 H6A 0.980 no . .
C6 H6B 0.980 no . .
C6 H6C 0.980 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C14 H14 0.950 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .
C17 H17 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C3 O3 C7 115.65(18) yes . . .
C7 O8 C9 116.72(18) yes . . .
N2 N1 C5 105.20(18) yes . . .
N1 N2 C3 110.28(18) yes . . .
N1 N2 C6 120.81(18) yes . . .
C3 N2 C6 128.79(19) yes . . .
O3 C3 N2 120.8(2) yes . . .
O3 C3 C4 128.3(2) yes . . .
N2 C3 C4 110.7(2) yes . . .
C3 C4 C5 102.31(19) yes . . .
C3 C4 C15 125.7(2) yes . . .
C5 C4 C15 131.9(2) yes . . .
N1 C5 C4 111.5(2) yes . . .
N1 C5 C16 118.84(19) yes . . .
C4 C5 C16 129.6(2) yes . . .
O3 C7 O7 126.0(2) yes . . .
O3 C7 O8 105.44(19) yes . . .
O7 C7 O8 128.6(2) yes . . .
O8 C9 C10 119.5(2) yes . . .
O8 C9 C14 117.4(2) yes . . .
C10 C9 C14 122.9(2) yes . . .
C9 C10 C11 118.4(2) yes . . .
C10 C11 C12 120.2(3) yes . . .
C11 C12 C13 120.0(3) yes . . .
C12 C13 C14 120.3(3) yes . . .
C9 C14 C13 118.3(2) yes . . .
C5 C16 C17 121.9(2) yes . . .
C5 C16 C21 120.41(19) yes . . .
C17 C16 C21 117.7(2) yes . . .
C16 C17 C18 121.1(2) yes . . .
C17 C18 C19 120.4(2) yes . . .
C18 C19 C20 119.4(2) yes . . .
C19 C20 C21 120.4(2) yes . . .
C16 C21 C20 120.9(2) yes . . .
N2 C6 H6A 109.472 no . . .
N2 C6 H6B 109.473 no . . .
N2 C6 H6C 109.458 no . . .
H6A C6 H6B 109.489 no . . .
H6A C6 H6C 109.466 no . . .
H6B C6 H6C 109.468 no . . .
C9 C10 H10 120.821 no . . .
C11 C10 H10 120.797 no . . .
C10 C11 H11 119.894 no . . .
C12 C11 H11 119.890 no . . .
C11 C12 H12 120.004 no . . .
C13 C12 H12 119.999 no . . .
C12 C13 H13 119.889 no . . .
C14 C13 H13 119.857 no . . .
C9 C14 H14 120.866 no . . .
C13 C14 H14 120.867 no . . .
C4 C15 H15A 109.473 no . . .
C4 C15 H15B 109.478 no . . .
C4 C15 H15C 109.466 no . . .
H15A C15 H15B 109.470 no . . .
H15A C15 H15C 109.463 no . . .
H15B C15 H15C 109.478 no . . .
C16 C17 H17 119.444 no . . .
C18 C17 H17 119.457 no . . .
C17 C18 H18 119.820 no . . .
C19 C18 H18 119.814 no . . .
C18 C19 H19 120.311 no . . .
C20 C19 H19 120.304 no . . .
C19 C20 H20 119.774 no . . .
C21 C20 H20 119.783 no . . .
C16 C21 H21 119.530 no . . .
C20 C21 H21 119.527 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 O3 C7 O7 5.6(3) no . . . .
C3 O3 C7 O8 -174.31(16) no . . . .
C7 O3 C3 N2 -87.0(2) no . . . .
C7 O3 C3 C4 97.7(3) no . . . .
C7 O8 C9 C10 81.5(3) no . . . .
C7 O8 C9 C14 -103.9(2) no . . . .
C9 O8 C7 O3 179.97(16) no . . . .
C9 O8 C7 O7 0.1(4) no . . . .
N2 N1 C5 C4 -0.1(2) no . . . .
N2 N1 C5 C16 -177.79(16) no . . . .
C5 N1 N2 C3 0.3(2) no . . . .
C5 N1 N2 C6 176.50(16) no . . . .
N1 N2 C3 O3 -176.55(18) no . . . .
N1 N2 C3 C4 -0.4(2) no . . . .
C6 N2 C3 O3 7.7(4) no . . . .
C6 N2 C3 C4 -176.2(2) no . . . .
O3 C3 C4 C5 176.1(2) no . . . .
O3 C3 C4 C15 -6.3(4) no . . . .
N2 C3 C4 C5 0.4(2) no . . . .
N2 C3 C4 C15 178.00(18) no . . . .
C3 C4 C5 N1 -0.2(2) no . . . .
C3 C4 C5 C16 177.2(2) no . . . .
C15 C4 C5 N1 -177.6(2) no . . . .
C15 C4 C5 C16 -0.2(4) no . . . .
N1 C5 C16 C17 -167.46(19) no . . . .
N1 C5 C16 C21 13.7(3) no . . . .
C4 C5 C16 C17 15.3(4) no . . . .
C4 C5 C16 C21 -163.5(2) no . . . .
O8 C9 C10 C11 174.25(18) no . . . .
O8 C9 C14 C13 -173.67(18) no . . . .
C10 C9 C14 C13 0.7(4) no . . . .
C14 C9 C10 C11 0.0(4) no . . . .
C9 C10 C11 C12 -1.0(4) no . . . .
C10 C11 C12 C13 1.4(4) no . . . .
C11 C12 C13 C14 -0.6(4) no . . . .
C12 C13 C14 C9 -0.4(4) no . . . .
C5 C16 C17 C18 -176.50(19) no . . . .
C5 C16 C21 C20 176.70(19) no . . . .
C17 C16 C21 C20 -2.2(3) no . . . .
C21 C16 C17 C18 2.3(3) no . . . .
C16 C17 C18 C19 -0.9(4) no . . . .
C17 C18 C19 C20 -0.7(4) no . . . .
C18 C19 C20 C21 0.9(4) no . . . .
C19 C20 C21 C16 0.6(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O3 N1 3.519(3) no . .
O3 C5 3.537(3) no . .
O3 C6 2.965(3) no . .
O3 C9 3.468(3) no . .
O3 C15 3.101(3) no . .
O7 N2 3.225(3) no . .
O7 C3 2.674(3) no . .
O7 C4 3.498(3) no . .
O7 C6 3.506(3) no . .
O7 C9 2.724(3) no . .
O7 C10 3.247(3) no . .
O7 C14 3.539(3) no . .
O8 C3 3.420(3) no . .
N1 C21 2.849(3) no . .
N2 C7 3.123(3) no . .
N2 C16 3.546(3) no . .
C4 C7 3.305(3) no . .
C4 C17 3.137(4) no . .
C5 C6 3.534(3) no . .
C6 C7 3.435(4) no . .
C7 C10 3.101(4) no . .
C7 C14 3.249(4) no . .
C9 C12 2.726(4) no . .
C10 C13 2.769(4) no . .
C11 C14 2.768(4) no . .
C15 C16 3.368(3) no . .
C15 C17 3.252(4) no . .
C16 C19 2.803(4) no . .
C17 C20 2.762(3) no . .
C18 C21 2.764(3) no . .
O3 C14 3.588(3) no . 2_655
O7 O8 3.579(3) no . 2_654
O8 O7 3.579(3) no . 2_655
O8 C15 3.517(3) no . 2_655
N1 C15 3.528(3) no . 1_565
N1 C20 3.488(3) no . 4_665
N2 C13 3.465(4) no . 2_655
C6 C12 3.538(4) no . 2_655
C6 C13 3.566(4) no . 2_655
C9 C15 3.528(4) no . 2_655
C11 C16 3.397(4) no . 2_655
C11 C21 3.566(4) no . 2_655
C12 C6 3.538(4) no . 2_654
C12 C17 3.495(4) no . 2_655
C12 C18 3.546(4) no . 2_655
C13 N2 3.465(4) no . 2_654
C13 C6 3.566(4) no . 2_654
C14 O3 3.588(3) no . 2_654
C15 O8 3.517(3) no . 2_654
C15 N1 3.528(3) no . 1_545
C15 C9 3.528(4) no . 2_654
C16 C11 3.397(4) no . 2_654
C17 C12 3.495(4) no . 2_654
C18 C12 3.546(4) no . 2_654
C20 N1 3.488(3) no . 4_664
C21 C11 3.566(4) no . 2_654
O3 H6A 3.2733 no . .
O3 H6B 2.7043 no . .
O3 H15B 2.7237 no . .
O7 H6A 3.1324 no . .
O7 H6B 3.5750 no . .
O7 H10 3.2323 no . .
O8 H10 2.5882 no . .
O8 H14 2.5497 no . .
N1 H6A 2.8965 no . .
N1 H6B 3.1809 no . .
N1 H6C 2.5305 no . .
N1 H21 2.5304 no . .
C3 H6A 2.9286 no . .
C3 H6B 2.6947 no . .
C3 H6C 3.2538 no . .
C3 H15A 3.1150 no . .
C3 H15B 2.6326 no . .
C3 H15C 3.1974 no . .
C4 H17 2.8540 no . .
C5 H15A 3.0132 no . .
C5 H15B 3.4088 no . .
C5 H15C 2.8979 no . .
C5 H17 2.6765 no . .
C5 H21 2.6549 no . .
C7 H6A 3.3520 no . .
C7 H6B 3.2255 no . .
C7 H10 3.0815 no . .
C7 H14 3.3242 no . .
C7 H15B 3.2029 no . .
C9 H11 3.2197 no . .
C9 H13 3.2249 no . .
C10 H12 3.2531 no . .
C10 H14 3.2594 no . .
C11 H13 3.2516 no . .
C12 H10 3.2593 no . .
C12 H14 3.2551 no . .
C13 H11 3.2501 no . .
C14 H10 3.2593 no . .
C14 H12 3.2507 no . .
C15 H17 2.5950 no . .
C16 H15A 3.5066 no . .
C16 H15C 3.2661 no . .
C16 H18 3.2741 no . .
C16 H20 3.2747 no . .
C17 H15A 3.1381 no . .
C17 H15C 2.9710 no . .
C17 H19 3.2572 no . .
C17 H21 3.2569 no . .
C18 H20 3.2487 no . .
C19 H17 3.2518 no . .
C19 H21 3.2549 no . .
C20 H18 3.2499 no . .
C21 H17 3.2572 no . .
C21 H19 3.2584 no . .
H10 H11 2.3371 no . .
H11 H12 2.3361 no . .
H12 H13 2.3252 no . .
H13 H14 2.3435 no . .
H15A H17 2.3242 no . .
H15B H17 3.5556 no . .
H15C H17 2.3631 no . .
H17 H18 2.3224 no . .
H18 H19 2.3339 no . .
H19 H20 2.3387 no . .
H20 H21 2.3188 no . .
O3 H6A 2.9183 no . 1_545
O3 H14 3.3018 no . 2_655
O7 H6B 2.9149 no . 2_654
O7 H10 3.2572 no . 2_654
O7 H15B 3.3527 no . 1_565
O8 H15B 3.2771 no . 2_655
O8 H15C 2.9730 no . 2_655
N1 H15A 2.5761 no . 1_565
N1 H18 3.2752 no . 4_655
N1 H19 3.5348 no . 4_655
N1 H19 3.1810 no . 4_665
N1 H20 2.7459 no . 4_665
N2 H13 3.4749 no . 2_655
N2 H15A 2.8876 no . 1_565
N2 H15B 3.5988 no . 1_565
N2 H20 3.4665 no . 4_665
C3 H6A 3.3101 no . 1_545
C4 H6A 3.3243 no . 1_545
C4 H19 3.1687 no . 4_655
C5 H15A 3.2874 no . 1_565
C5 H18 3.2711 no . 4_655
C5 H19 2.9041 no . 4_655
C6 H14 3.0088 no . 2_665
C6 H15A 3.1313 no . 1_565
C6 H15B 3.4773 no . 1_565
C9 H6B 3.0292 no . 2_654
C9 H15C 2.7511 no . 2_655
C10 H6B 3.1574 no . 2_654
C10 H15A 3.4943 no . 2_665
C10 H15C 3.2069 no . 2_655
C10 H15C 3.3734 no . 2_665
C11 H6B 3.2796 no . 2_654
C11 H6C 3.1921 no . 2_654
C11 H14 3.5518 no . 1_565
C11 H15A 3.5445 no . 2_665
C11 H15C 3.3589 no . 2_665
C11 H17 3.5596 no . 2_665
C12 H6B 3.3148 no . 2_654
C12 H6C 3.0918 no . 2_654
C12 H20 3.0740 no . 3_565
C13 H6B 3.2028 no . 2_654
C13 H6C 3.3530 no . 2_644
C13 H6C 3.4791 no . 2_654
C13 H15C 3.5090 no . 2_655
C14 H6B 3.0621 no . 2_654
C14 H6C 3.2657 no . 2_644
C14 H11 3.5273 no . 1_545
C14 H15C 2.9393 no . 2_655
C15 H6A 3.0017 no . 1_545
C15 H10 3.0188 no . 2_644
C15 H11 3.2942 no . 2_644
C16 H11 3.3947 no . 2_654
C16 H18 3.0109 no . 4_655
C16 H19 3.0472 no . 4_655
C17 H11 3.3804 no . 2_644
C17 H12 3.5789 no . 2_654
C17 H19 3.1137 no . 4_655
C17 H21 3.0683 no . 1_545
C18 H12 3.2941 no . 2_654
C18 H12 3.5441 no . 3_455
C18 H13 3.2676 no . 3_455
C18 H20 3.1651 no . 1_545
C18 H21 3.4329 no . 1_545
C19 H6C 3.5312 no . 4_664
C19 H12 3.1879 no . 2_654
C19 H13 2.8207 no . 3_455
C19 H21 3.2364 no . 4_664
C20 H6C 3.4208 no . 4_664
C20 H12 3.3904 no . 2_654
C20 H12 2.9933 no . 3_465
C20 H13 3.2536 no . 3_455
C20 H18 3.0659 no . 1_565
C20 H21 3.3931 no . 4_664
C21 H11 3.2208 no . 2_654
C21 H12 3.1833 no . 3_465
C21 H17 3.1390 no . 1_565
C21 H18 3.4280 no . 1_565
C21 H18 3.0563 no . 4_655
H6A O3 2.9183 no . 1_565
H6A C3 3.3101 no . 1_565
H6A C4 3.3243 no . 1_565
H6A C15 3.0017 no . 1_565
H6A H14 2.9460 no . 2_665
H6A H15A 2.7086 no . 1_565
H6A H15B 2.6741 no . 1_565
H6B O7 2.9149 no . 2_655
H6B C9 3.0292 no . 2_655
H6B C10 3.1574 no . 2_655
H6B C11 3.2796 no . 2_655
H6B C12 3.3148 no . 2_655
H6B C13 3.2028 no . 2_655
H6B C14 3.0621 no . 2_655
H6B H14 3.5175 no . 2_655
H6B H14 2.9772 no . 2_665
H6C C11 3.1921 no . 2_655
H6C C12 3.0918 no . 2_655
H6C C13 3.4791 no . 2_655
H6C C13 3.3530 no . 2_665
H6C C14 3.2657 no . 2_665
H6C C19 3.5312 no . 4_665
H6C C20 3.4208 no . 4_665
H6C H11 3.4411 no . 2_655
H6C H12 3.3014 no . 2_655
H6C H13 2.7708 no . 2_665
H6C H14 2.6025 no . 2_665
H6C H15A 3.3004 no . 1_565
H6C H19 3.1130 no . 4_665
H6C H20 2.8837 no . 4_665
H10 O7 3.2572 no . 2_655
H10 C15 3.0188 no . 2_665
H10 H14 3.5269 no . 1_565
H10 H15A 2.8938 no . 2_665
H10 H15B 2.8807 no . 2_665
H10 H15C 2.7659 no . 2_665
H11 C14 3.5273 no . 1_565
H11 C15 3.2942 no . 2_665
H11 C16 3.3947 no . 2_655
H11 C17 3.3804 no . 2_665
H11 C21 3.2208 no . 2_655
H11 H6C 3.4411 no . 2_654
H11 H13 3.4900 no . 1_565
H11 H14 3.3525 no . 1_565
H11 H15A 2.9904 no . 2_665
H11 H15C 2.7213 no . 2_665
H11 H17 2.6425 no . 2_665
H11 H18 3.3357 no . 2_665
H11 H21 3.2944 no . 2_655
H12 C17 3.5789 no . 2_655
H12 C18 3.2941 no . 2_655
H12 C18 3.5441 no . 3_555
H12 C19 3.1879 no . 2_655
H12 C20 3.3904 no . 2_655
H12 C20 2.9933 no . 3_565
H12 C21 3.1833 no . 3_565
H12 H6C 3.3014 no . 2_654
H12 H18 3.5186 no . 3_555
H12 H19 3.5073 no . 2_655
H12 H20 2.4227 no . 3_565
H12 H21 2.7930 no . 3_565
H13 N2 3.4749 no . 2_654
H13 C18 3.2676 no . 3_555
H13 C19 2.8207 no . 3_555
H13 C20 3.2536 no . 3_555
H13 H6C 2.7708 no . 2_644
H13 H11 3.4900 no . 1_545
H13 H18 3.5150 no . 3_555
H13 H19 2.7978 no . 3_555
H13 H20 3.4896 no . 3_555
H14 O3 3.3017 no . 2_654
H14 C6 3.0088 no . 2_644
H14 C11 3.5518 no . 1_545
H14 H6A 2.9460 no . 2_644
H14 H6B 2.9772 no . 2_644
H14 H6B 3.5175 no . 2_654
H14 H6C 2.6025 no . 2_644
H14 H10 3.5269 no . 1_545
H14 H11 3.3525 no . 1_545
H14 H15C 3.2182 no . 2_655
H15A N1 2.5761 no . 1_545
H15A N2 2.8876 no . 1_545
H15A C5 3.2874 no . 1_545
H15A C6 3.1313 no . 1_545
H15A C10 3.4943 no . 2_644
H15A C11 3.5445 no . 2_644
H15A H6A 2.7086 no . 1_545
H15A H6C 3.3004 no . 1_545
H15A H10 2.8938 no . 2_644
H15A H11 2.9904 no . 2_644
H15A H19 3.1047 no . 4_655
H15A H21 3.2124 no . 1_545
H15B O7 3.3527 no . 1_545
H15B O8 3.2771 no . 2_654
H15B N2 3.5988 no . 1_545
H15B C6 3.4773 no . 1_545
H15B H6A 2.6741 no . 1_545
H15B H10 2.8807 no . 2_644
H15C O8 2.9730 no . 2_654
H15C C9 2.7511 no . 2_654
H15C C10 3.3734 no . 2_644
H15C C10 3.2069 no . 2_654
H15C C11 3.3589 no . 2_644
H15C C13 3.5090 no . 2_654
H15C C14 2.9393 no . 2_654
H15C H10 2.7659 no . 2_644
H15C H11 2.7213 no . 2_644
H15C H14 3.2182 no . 2_654
H17 C11 3.5596 no . 2_644
H17 C21 3.1390 no . 1_545
H17 H11 2.6425 no . 2_644
H17 H19 2.9269 no . 4_655
H17 H21 2.4925 no . 1_545
H18 N1 3.2752 no . 4_654
H18 C5 3.2711 no . 4_654
H18 C16 3.0109 no . 4_654
H18 C20 3.0659 no . 1_545
H18 C21 3.4280 no . 1_545
H18 C21 3.0563 no . 4_654
H18 H11 3.3357 no . 2_644
H18 H12 3.5186 no . 3_455
H18 H13 3.5150 no . 3_455
H18 H20 2.5086 no . 1_545
H18 H21 3.2043 no . 1_545
H18 H21 3.1278 no . 4_654
H19 N1 3.5348 no . 4_654
H19 N1 3.1810 no . 4_664
H19 C4 3.1687 no . 4_654
H19 C5 2.9041 no . 4_654
H19 C16 3.0472 no . 4_654
H19 C17 3.1137 no . 4_654
H19 H6C 3.1130 no . 4_664
H19 H12 3.5073 no . 2_654
H19 H13 2.7978 no . 3_455
H19 H15A 3.1047 no . 4_654
H19 H17 2.9269 no . 4_654
H19 H21 2.8750 no . 4_664
H20 N1 2.7459 no . 4_664
H20 N2 3.4665 no . 4_664
H20 C12 3.0740 no . 3_465
H20 C18 3.1651 no . 1_565
H20 H6C 2.8837 no . 4_664
H20 H12 2.4227 no . 3_465
H20 H13 3.4896 no . 3_455
H20 H18 2.5086 no . 1_565
H20 H21 3.1699 no . 4_664
H21 C17 3.0683 no . 1_565
H21 C18 3.4329 no . 1_565
H21 C19 3.2364 no . 4_665
H21 C20 3.3931 no . 4_665
H21 H11 3.2944 no . 2_654
H21 H12 2.7930 no . 3_465
H21 H15A 3.2124 no . 1_565
H21 H17 2.4925 no . 1_565
H21 H18 3.2043 no . 1_565
H21 H18 3.1278 no . 4_655
H21 H19 2.8750 no . 4_665
H21 H20 3.1699 no . 4_665

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 987863'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_S23


_chemical_formula_sum            'C19 H18 N2 O3'
_chemical_formula_moiety         'C19 H18 N2 O3'
_chemical_formula_weight         322.36
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.504(4)
_cell_length_b                   26.450(14)
_cell_length_c                   11.354(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.550(16)
_cell_angle_gamma                90.0000
_cell_volume                     1647.9(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1202
_cell_measurement_theta_min      41.07
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680.00
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  ?
_diffrn_reflns_number            17146
_diffrn_reflns_av_R_equivalents  0.1454
_diffrn_reflns_theta_max         68.17
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3008
_reflns_number_gt                2107
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0949
_refine_ls_wR_factor_ref         0.3124
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3008
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.620
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
O14 O 0.2001(4) 0.13399(8) 0.8148(2) 0.0535(7) Uani 1.0 4 d . . .
O15 O 0.0164(5) 0.19009(9) 0.9295(2) 0.0610(8) Uani 1.0 4 d . . .
O16 O 0.3710(5) 0.15041(9) 0.9866(2) 0.0586(8) Uani 1.0 4 d . . .
N1 N -0.0412(5) 0.16335(9) 0.6451(3) 0.0507(8) Uani 1.0 4 d . . .
N2 N -0.2441(5) 0.15046(10) 0.5759(3) 0.0548(8) Uani 1.0 4 d . . .
C1 C 0.1110(8) 0.20610(13) 0.6154(4) 0.0623(10) Uani 1.0 4 d . . .
C3 C -0.3290(6) 0.10879(12) 0.6270(3) 0.0512(8) Uani 1.0 4 d . . .
C4 C -0.1842(6) 0.09522(12) 0.7299(3) 0.0485(8) Uani 1.0 4 d . . .
C5 C -0.0047(6) 0.13119(11) 0.7361(3) 0.0475(8) Uani 1.0 4 d . . .
C6 C -0.5511(7) 0.08246(14) 0.5723(4) 0.0621(10) Uani 1.0 4 d . . .
C7 C -0.2029(6) 0.05118(13) 0.8110(3) 0.0569(9) Uani 1.0 4 d . . .
C8 C -0.0354(6) 0.00796(12) 0.7832(3) 0.0524(9) Uani 1.0 4 d . . .
C9 C -0.0644(6) -0.01680(12) 0.6756(4) 0.0592(10) Uani 1.0 4 d . . .
C10 C 0.0904(7) -0.05528(14) 0.6473(4) 0.0659(10) Uani 1.0 4 d . . .
C11 C 0.2781(7) -0.06985(14) 0.7279(4) 0.0648(10) Uani 1.0 4 d . . .
C12 C 0.3128(7) -0.04594(15) 0.8358(4) 0.0691(11) Uani 1.0 4 d . . .
C13 C 0.1564(7) -0.00664(13) 0.8630(4) 0.0609(10) Uani 1.0 4 d . . .
C15 C 0.1771(6) 0.16153(12) 0.9137(3) 0.0493(8) Uani 1.0 4 d . . .
C17 C 0.3809(6) 0.17162(12) 1.1015(3) 0.0511(9) Uani 1.0 4 d . . .
C18 C 0.2121(6) 0.15692(13) 1.1792(3) 0.0557(9) Uani 1.0 4 d . . .
C19 C 0.2391(7) 0.17521(14) 1.2932(3) 0.0582(9) Uani 1.0 4 d . . .
C20 C 0.4326(7) 0.20699(14) 1.3285(4) 0.0612(10) Uani 1.0 4 d . . .
C21 C 0.5989(7) 0.22071(15) 1.2494(4) 0.0621(10) Uani 1.0 4 d . . .
C22 C 0.5752(6) 0.20270(14) 1.1337(3) 0.0570(9) Uani 1.0 4 d . . .
H1A H 0.2740 0.1939 0.6007 0.0747 Uiso 1.0 4 calc R . .
H1B H 0.1237 0.2302 0.6812 0.0747 Uiso 1.0 4 calc R . .
H1C H 0.0374 0.2229 0.5443 0.0747 Uiso 1.0 4 calc R . .
H6A H -0.5212 0.0712 0.4925 0.0745 Uiso 1.0 4 calc R . .
H6B H -0.6896 0.1059 0.5680 0.0745 Uiso 1.0 4 calc R . .
H6C H -0.5878 0.0532 0.6206 0.0745 Uiso 1.0 4 calc R . .
H7A H -0.3733 0.0389 0.8052 0.0682 Uiso 1.0 4 calc R . .
H7B H -0.1620 0.0624 0.8934 0.0682 Uiso 1.0 4 calc R . .
H9 H -0.1938 -0.0071 0.6199 0.0711 Uiso 1.0 4 calc R . .
H10 H 0.0678 -0.0716 0.5727 0.0791 Uiso 1.0 4 calc R . .
H11 H 0.3839 -0.0965 0.7090 0.0778 Uiso 1.0 4 calc R . .
H12 H 0.4420 -0.0561 0.8912 0.0829 Uiso 1.0 4 calc R . .
H13 H 0.1816 0.0102 0.9368 0.0731 Uiso 1.0 4 calc R . .
H18 H 0.0817 0.1349 1.1547 0.0669 Uiso 1.0 4 calc R . .
H19 H 0.1249 0.1661 1.3480 0.0699 Uiso 1.0 4 calc R . .
H20 H 0.4504 0.2193 1.4073 0.0734 Uiso 1.0 4 calc R . .
H21 H 0.7303 0.2425 1.2740 0.0745 Uiso 1.0 4 calc R . .
H22 H 0.6896 0.2116 1.0788 0.0684 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b6 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b6'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b6'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
O14 C5 1.384(4) yes . .
O14 C15 1.353(4) yes . .
O15 C15 1.188(4) yes . .
O16 C15 1.330(4) yes . .
O16 C17 1.417(4) yes . .
N1 N2 1.357(4) yes . .
N1 C1 1.463(5) yes . .
N1 C5 1.341(4) yes . .
N2 C3 1.346(5) yes . .
C3 C4 1.407(5) yes . .
C3 C6 1.498(5) yes . .
C4 C5 1.369(5) yes . .
C4 C7 1.494(5) yes . .
C7 C8 1.518(5) yes . .
C8 C9 1.384(5) yes . .
C8 C13 1.390(5) yes . .
C9 C10 1.382(5) yes . .
C10 C11 1.380(6) yes . .
C11 C12 1.378(6) yes . .
C12 C13 1.400(6) yes . .
C17 C18 1.387(5) yes . .
C17 C22 1.375(5) yes . .
C18 C19 1.378(5) yes . .
C19 C20 1.391(6) yes . .
C20 C21 1.381(6) yes . .
C21 C22 1.394(6) yes . .
C1 H1A 0.980 no . .
C1 H1B 0.980 no . .
C1 H1C 0.980 no . .
C6 H6A 0.980 no . .
C6 H6B 0.980 no . .
C6 H6C 0.980 no . .
C7 H7A 0.990 no . .
C7 H7B 0.990 no . .
C9 H9 0.950 no . .
C10 H10 0.950 no . .
C11 H11 0.950 no . .
C12 H12 0.950 no . .
C13 H13 0.950 no . .
C18 H18 0.950 no . .
C19 H19 0.950 no . .
C20 H20 0.950 no . .
C21 H21 0.950 no . .
C22 H22 0.950 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C5 O14 C15 116.1(3) yes . . .
C15 O16 C17 117.1(3) yes . . .
N2 N1 C1 121.4(3) yes . . .
N2 N1 C5 110.6(3) yes . . .
C1 N1 C5 127.9(3) yes . . .
N1 N2 C3 104.7(3) yes . . .
N2 C3 C4 111.9(3) yes . . .
N2 C3 C6 120.1(3) yes . . .
C4 C3 C6 128.0(3) yes . . .
C3 C4 C5 103.0(3) yes . . .
C3 C4 C7 130.4(3) yes . . .
C5 C4 C7 126.5(3) yes . . .
O14 C5 N1 121.9(3) yes . . .
O14 C5 C4 128.2(3) yes . . .
N1 C5 C4 109.7(3) yes . . .
C4 C7 C8 112.7(3) yes . . .
C7 C8 C9 120.7(3) yes . . .
C7 C8 C13 121.1(3) yes . . .
C9 C8 C13 118.2(3) yes . . .
C8 C9 C10 121.6(4) yes . . .
C9 C10 C11 119.6(4) yes . . .
C10 C11 C12 120.3(4) yes . . .
C11 C12 C13 119.5(4) yes . . .
C8 C13 C12 120.7(4) yes . . .
O14 C15 O15 126.0(3) yes . . .
O14 C15 O16 105.9(3) yes . . .
O15 C15 O16 128.1(3) yes . . .
O16 C17 C18 119.8(3) yes . . .
O16 C17 C22 117.0(3) yes . . .
C18 C17 C22 123.0(3) yes . . .
C17 C18 C19 118.1(4) yes . . .
C18 C19 C20 120.4(4) yes . . .
C19 C20 C21 120.3(4) yes . . .
C20 C21 C22 120.4(4) yes . . .
C17 C22 C21 117.9(4) yes . . .
N1 C1 H1A 109.465 no . . .
N1 C1 H1B 109.478 no . . .
N1 C1 H1C 109.474 no . . .
H1A C1 H1B 109.473 no . . .
H1A C1 H1C 109.473 no . . .
H1B C1 H1C 109.464 no . . .
C3 C6 H6A 109.474 no . . .
C3 C6 H6B 109.464 no . . .
C3 C6 H6C 109.467 no . . .
H6A C6 H6B 109.471 no . . .
H6A C6 H6C 109.478 no . . .
H6B C6 H6C 109.473 no . . .
C4 C7 H7A 109.049 no . . .
C4 C7 H7B 109.042 no . . .
C8 C7 H7A 109.048 no . . .
C8 C7 H7B 109.052 no . . .
H7A C7 H7B 107.813 no . . .
C8 C9 H9 119.201 no . . .
C10 C9 H9 119.198 no . . .
C9 C10 H10 120.184 no . . .
C11 C10 H10 120.187 no . . .
C10 C11 H11 119.832 no . . .
C12 C11 H11 119.821 no . . .
C11 C12 H12 120.244 no . . .
C13 C12 H12 120.247 no . . .
C8 C13 H13 119.631 no . . .
C12 C13 H13 119.637 no . . .
C17 C18 H18 120.934 no . . .
C19 C18 H18 120.930 no . . .
C18 C19 H19 119.830 no . . .
C20 C19 H19 119.819 no . . .
C19 C20 H20 119.866 no . . .
C21 C20 H20 119.857 no . . .
C20 C21 H21 119.817 no . . .
C22 C21 H21 119.820 no . . .
C17 C22 H22 121.056 no . . .
C21 C22 H22 121.056 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 O14 C15 O15 -14.0(5) no . . . .
C5 O14 C15 O16 167.0(3) no . . . .
C15 O14 C5 N1 93.6(4) no . . . .
C15 O14 C5 C4 -92.5(4) no . . . .
C15 O16 C17 C18 66.1(4) no . . . .
C15 O16 C17 C22 -119.9(3) no . . . .
C17 O16 C15 O14 -175.2(3) no . . . .
C17 O16 C15 O15 5.8(5) no . . . .
C1 N1 N2 C3 177.3(3) no . . . .
N2 N1 C5 O14 175.2(3) no . . . .
N2 N1 C5 C4 0.3(4) no . . . .
C5 N1 N2 C3 -0.8(4) no . . . .
C1 N1 C5 O14 -2.6(5) no . . . .
C1 N1 C5 C4 -177.6(3) no . . . .
N1 N2 C3 C4 1.0(4) no . . . .
N1 N2 C3 C6 -178.2(3) no . . . .
N2 C3 C4 C5 -0.8(4) no . . . .
N2 C3 C4 C7 -177.2(3) no . . . .
C6 C3 C4 C5 178.3(3) no . . . .
C6 C3 C4 C7 1.9(6) no . . . .
C3 C4 C5 O14 -174.3(3) no . . . .
C3 C4 C5 N1 0.3(4) no . . . .
C3 C4 C7 C8 96.8(4) no . . . .
C5 C4 C7 C8 -78.8(4) no . . . .
C7 C4 C5 O14 2.3(6) no . . . .
C7 C4 C5 N1 176.9(3) no . . . .
C4 C7 C8 C9 -62.7(4) no . . . .
C4 C7 C8 C13 114.9(3) no . . . .
C7 C8 C9 C10 178.2(3) no . . . .
C7 C8 C13 C12 -178.8(3) no . . . .
C9 C8 C13 C12 -1.1(5) no . . . .
C13 C8 C9 C10 0.5(5) no . . . .
C8 C9 C10 C11 0.4(6) no . . . .
C9 C10 C11 C12 -0.6(6) no . . . .
C10 C11 C12 C13 -0.1(6) no . . . .
C11 C12 C13 C8 1.0(6) no . . . .
O16 C17 C18 C19 174.9(3) no . . . .
O16 C17 C22 C21 -175.0(3) no . . . .
C18 C17 C22 C21 -1.2(5) no . . . .
C22 C17 C18 C19 1.3(5) no . . . .
C17 C18 C19 C20 -0.8(5) no . . . .
C18 C19 C20 C21 0.3(6) no . . . .
C19 C20 C21 C22 -0.3(6) no . . . .
C20 C21 C22 C17 0.7(6) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O14 N2 3.531(4) no . .
O14 C1 2.971(5) no . .
O14 C3 3.534(4) no . .
O14 C7 3.115(5) no . .
O14 C8 3.584(5) no . .
O14 C17 3.473(5) no . .
O15 N1 3.297(4) no . .
O15 C4 3.501(4) no . .
O15 C5 2.688(4) no . .
O15 C17 2.730(4) no . .
O15 C18 3.080(5) no . .
O16 C5 3.420(4) no . .
N1 C6 3.573(5) no . .
N1 C15 3.189(5) no . .
C1 C3 3.544(5) no . .
C1 C15 3.578(6) no . .
C3 C8 3.524(5) no . .
C4 C9 3.108(5) no . .
C4 C13 3.551(5) no . .
C4 C15 3.276(5) no . .
C5 C8 3.310(5) no . .
C6 C7 3.299(5) no . .
C8 C11 2.789(5) no . .
C9 C12 2.759(6) no . .
C10 C13 2.765(6) no . .
C15 C18 3.008(5) no . .
C15 C22 3.370(5) no . .
C17 C20 2.735(5) no . .
C18 C21 2.783(5) no . .
C19 C22 2.786(6) no . .
O14 C3 3.547(5) no . 1_655
O14 C6 3.451(5) no . 1_655
O15 C1 3.477(5) no . 4_555
O15 C22 3.504(5) no . 1_455
N1 C6 3.591(5) no . 1_655
N2 C20 3.536(5) no . 1_454
C1 O15 3.477(5) no . 4_554
C1 C17 3.568(5) no . 4_554
C1 C21 3.554(6) no . 4_554
C1 C22 3.508(6) no . 4_554
C3 O14 3.547(5) no . 1_455
C5 C6 3.477(5) no . 1_655
C6 O14 3.451(5) no . 1_455
C6 N1 3.591(5) no . 1_455
C6 C5 3.477(5) no . 1_455
C17 C1 3.568(5) no . 4_555
C20 N2 3.536(5) no . 1_656
C21 C1 3.554(6) no . 4_555
C22 O15 3.504(5) no . 1_655
C22 C1 3.508(6) no . 4_555
O14 H1A 2.9568 no . .
O14 H1B 2.9742 no . .
O14 H7B 2.9381 no . .
O14 H13 3.5591 no . .
O15 H1B 3.1121 no . .
O15 H7B 3.5311 no . .
O15 H18 2.9417 no . .
O16 H18 2.6133 no . .
O16 H22 2.5496 no . .
N2 H1A 3.0663 no . .
N2 H1B 3.0964 no . .
N2 H1C 2.5079 no . .
N2 H6A 2.7188 no . .
N2 H6B 2.7166 no . .
N2 H6C 3.2579 no . .
C3 H7A 2.7656 no . .
C3 H7B 3.3245 no . .
C3 H9 3.1569 no . .
C4 H6A 3.2115 no . .
C4 H6B 3.2229 no . .
C4 H6C 2.6974 no . .
C4 H9 2.9792 no . .
C5 H1A 2.8003 no . .
C5 H1B 2.7948 no . .
C5 H1C 3.2800 no . .
C5 H7A 3.3085 no . .
C5 H7B 2.7369 no . .
C6 H7A 2.9777 no . .
C6 H9 3.0988 no . .
C7 H6C 2.9049 no . .
C7 H9 2.6655 no . .
C7 H13 2.6857 no . .
C8 H10 3.2682 no . .
C8 H12 3.2807 no . .
C9 H6C 3.4394 no . .
C9 H7A 2.7605 no . .
C9 H7B 3.3174 no . .
C9 H11 3.2446 no . .
C9 H13 3.2408 no . .
C10 H12 3.2506 no . .
C11 H9 3.2405 no . .
C11 H13 3.2552 no . .
C12 H10 3.2501 no . .
C13 H7A 3.1746 no . .
C13 H7B 2.5739 no . .
C13 H9 3.2390 no . .
C13 H11 3.2594 no . .
C15 H1B 3.1983 no . .
C15 H7B 3.2154 no . .
C15 H18 2.9130 no . .
C15 H22 3.5195 no . .
C17 H19 3.2350 no . .
C17 H21 3.2341 no . .
C18 H20 3.2570 no . .
C18 H22 3.2825 no . .
C19 H21 3.2595 no . .
C20 H18 3.2651 no . .
C20 H22 3.2689 no . .
C21 H19 3.2580 no . .
C22 H18 3.2801 no . .
C22 H20 3.2636 no . .
H6A H9 3.0348 no . .
H6B H7A 3.5606 no . .
H6C H7A 2.3526 no . .
H6C H9 2.6916 no . .
H7A H9 2.6849 no . .
H7A H13 3.3783 no . .
H7B H13 2.3619 no . .
H9 H10 2.3227 no . .
H10 H11 2.3298 no . .
H11 H12 2.3291 no . .
H12 H13 2.3482 no . .
H18 H19 2.3393 no . .
H19 H20 2.3360 no . .
H20 H21 2.3259 no . .
H21 H22 2.3564 no . .
O14 H6B 3.0074 no . 1_655
O14 H6C 3.3473 no . 1_655
O14 H7A 3.4492 no . 1_655
O15 H1B 3.5635 no . 4_555
O15 H1C 2.6430 no . 4_555
O15 H20 3.4071 no . 4_554
O15 H21 2.8862 no . 4_454
O15 H22 2.6303 no . 1_455
O16 H12 2.9977 no . 3_657
O16 H20 3.5969 no . 4_554
N1 H6B 2.6635 no . 1_655
N1 H10 3.4595 no . 3_556
N1 H19 3.5653 no . 1_554
N1 H21 3.1956 no . 4_454
N2 H1A 2.9246 no . 1_455
N2 H6B 3.2800 no . 1_655
N2 H10 2.8983 no . 3_556
N2 H11 3.5638 no . 3_556
N2 H19 3.4392 no . 1_554
N2 H20 3.0500 no . 1_454
C1 H6B 2.9356 no . 1_655
C1 H19 3.2221 no . 1_554
C1 H20 3.1457 no . 1_554
C1 H21 3.1750 no . 4_454
C1 H22 3.1842 no . 4_454
C3 H1A 3.1347 no . 1_455
C3 H10 2.9490 no . 3_556
C4 H6B 3.4149 no . 1_655
C4 H10 3.5991 no . 3_556
C5 H6B 2.7615 no . 1_655
C5 H6C 3.4241 no . 1_655
C6 H1A 3.1249 no . 1_455
C6 H9 3.1971 no . 3_456
C6 H10 3.1843 no . 3_456
C6 H10 3.2507 no . 3_556
C6 H11 3.4136 no . 3_556
C7 H13 3.2857 no . 3_557
C8 H6C 3.4103 no . 1_655
C8 H13 3.3745 no . 3_557
C9 H6A 3.1981 no . 3_456
C9 H6C 3.3098 no . 1_655
C10 H6A 3.4245 no . 3_456
C10 H6A 2.9860 no . 3_556
C10 H6B 3.4316 no . 3_456
C10 H6C 3.3970 no . 1_655
C10 H9 3.5391 no . 3_556
C10 H18 3.2744 no . 3_557
C10 H19 3.1628 no . 3_557
C11 H6A 2.9307 no . 3_556
C11 H6C 3.5717 no . 1_655
C11 H7A 3.5289 no . 1_655
C11 H18 3.0122 no . 3_557
C11 H19 3.4402 no . 3_557
C12 H7A 2.8694 no . 1_655
C12 H7B 3.2774 no . 3_557
C12 H18 3.2086 no . 3_557
C13 H6C 3.5600 no . 1_655
C13 H7A 2.9751 no . 1_655
C13 H7B 3.1333 no . 3_557
C13 H13 3.0505 no . 3_557
C15 H1C 3.5092 no . 4_555
C15 H20 3.4955 no . 4_554
C17 H1B 3.1265 no . 4_555
C17 H1C 3.4034 no . 4_555
C17 H11 3.1326 no . 3_657
C17 H12 3.2077 no . 3_657
C18 H1B 3.0265 no . 4_555
C18 H11 2.9429 no . 3_657
C18 H12 3.4097 no . 3_657
C18 H22 3.3385 no . 1_455
C19 H1A 3.5157 no . 1_556
C19 H1B 2.8561 no . 4_555
C19 H1C 3.3845 no . 1_556
C19 H11 2.9410 no . 3_657
C19 H21 3.3113 no . 1_455
C20 H1A 3.2959 no . 1_556
C20 H1B 2.8281 no . 4_555
C20 H1C 3.4295 no . 1_556
C20 H11 3.1321 no . 3_657
C21 H1A 3.2675 no . 4_555
C21 H1B 2.9680 no . 4_555
C21 H1B 3.3147 no . 4_655
C21 H11 3.3194 no . 3_657
C21 H19 3.3480 no . 1_655
C22 H1A 3.2053 no . 4_555
C22 H1B 3.1357 no . 4_555
C22 H1B 3.5076 no . 4_655
C22 H1C 3.4331 no . 4_655
C22 H11 3.3268 no . 3_657
C22 H18 3.3080 no . 1_655
C22 H20 3.3251 no . 4_554
H1A N2 2.9246 no . 1_655
H1A C3 3.1347 no . 1_655
H1A C6 3.1249 no . 1_655
H1A C19 3.5157 no . 1_554
H1A C20 3.2959 no . 1_554
H1A C21 3.2675 no . 4_554
H1A C22 3.2053 no . 4_554
H1A H6B 2.3688 no . 1_655
H1A H19 3.0121 no . 1_554
H1A H20 2.5606 no . 1_554
H1A H21 3.4969 no . 4_554
H1A H22 3.4108 no . 4_554
H1B O15 3.5635 no . 4_554
H1B C17 3.1265 no . 4_554
H1B C18 3.0265 no . 4_554
H1B C19 2.8561 no . 4_554
H1B C20 2.8281 no . 4_554
H1B C21 3.3147 no . 4_454
H1B C21 2.9680 no . 4_554
H1B C22 3.5076 no . 4_454
H1B C22 3.1357 no . 4_554
H1B H18 3.5889 no . 4_554
H1B H19 3.3345 no . 4_554
H1B H20 3.2977 no . 4_554
H1B H21 2.5851 no . 4_454
H1B H21 3.4961 no . 4_554
H1B H22 2.9990 no . 4_454
H1C O15 2.6430 no . 4_554
H1C C15 3.5092 no . 4_554
H1C C17 3.4034 no . 4_554
H1C C19 3.3845 no . 1_554
H1C C20 3.4295 no . 1_554
H1C C22 3.4331 no . 4_454
H1C H6B 3.4424 no . 1_655
H1C H19 2.7627 no . 1_554
H1C H20 3.4749 no . 1_454
H1C H20 2.8565 no . 1_554
H1C H21 3.4241 no . 1_454
H1C H21 3.3458 no . 4_454
H1C H22 2.6343 no . 4_454
H6A C9 3.1981 no . 3_456
H6A C10 3.4245 no . 3_456
H6A C10 2.9860 no . 3_556
H6A C11 2.9307 no . 3_556
H6A H6C 3.5980 no . 3_456
H6A H9 2.5778 no . 3_456
H6A H10 3.0412 no . 3_456
H6A H10 2.6590 no . 3_556
H6A H11 2.5554 no . 3_556
H6A H19 3.5046 no . 1_454
H6B O14 3.0074 no . 1_455
H6B N1 2.6635 no . 1_455
H6B N2 3.2800 no . 1_455
H6B C1 2.9356 no . 1_455
H6B C4 3.4149 no . 1_455
H6B C5 2.7615 no . 1_455
H6B C10 3.4316 no . 3_456
H6B H1A 2.3688 no . 1_455
H6B H1C 3.4424 no . 1_455
H6B H9 3.4012 no . 3_456
H6B H10 2.6792 no . 3_456
H6B H19 3.0683 no . 1_454
H6C O14 3.3473 no . 1_455
H6C C5 3.4241 no . 1_455
H6C C8 3.4103 no . 1_455
H6C C9 3.3098 no . 1_455
H6C C10 3.3970 no . 1_455
H6C C11 3.5717 no . 1_455
H6C C13 3.5600 no . 1_455
H6C H6A 3.5980 no . 3_456
H6C H9 3.1410 no . 3_456
H6C H10 3.3343 no . 3_456
H7A O14 3.4492 no . 1_455
H7A C11 3.5289 no . 1_455
H7A C12 2.8694 no . 1_455
H7A C13 2.9751 no . 1_455
H7A H12 2.9069 no . 1_455
H7A H12 3.5268 no . 3_557
H7A H13 3.0647 no . 1_455
H7A H13 3.3005 no . 3_557
H7B C12 3.2774 no . 3_557
H7B C13 3.1333 no . 3_557
H7B H12 2.9969 no . 3_557
H7B H13 2.7308 no . 3_557
H9 C6 3.1971 no . 3_456
H9 C10 3.5391 no . 3_556
H9 H6A 2.5778 no . 3_456
H9 H6B 3.4012 no . 3_456
H9 H6C 3.1410 no . 3_456
H9 H10 3.1369 no . 3_556
H9 H11 3.5199 no . 1_455
H10 N1 3.4595 no . 3_556
H10 N2 2.8983 no . 3_556
H10 C3 2.9490 no . 3_556
H10 C4 3.5991 no . 3_556
H10 C6 3.1843 no . 3_456
H10 C6 3.2507 no . 3_556
H10 H6A 3.0412 no . 3_456
H10 H6A 2.6590 no . 3_556
H10 H6B 2.6792 no . 3_456
H10 H6C 3.3343 no . 3_456
H10 H9 3.1369 no . 3_556
H10 H19 2.8858 no . 3_557
H11 N2 3.5638 no . 3_556
H11 C6 3.4136 no . 3_556
H11 C17 3.1326 no . 3_657
H11 C18 2.9429 no . 3_657
H11 C19 2.9410 no . 3_657
H11 C20 3.1321 no . 3_657
H11 C21 3.3194 no . 3_657
H11 C22 3.3268 no . 3_657
H11 H6A 2.5554 no . 3_556
H11 H9 3.5199 no . 1_655
H11 H18 3.2592 no . 3_557
H11 H18 3.3701 no . 3_657
H11 H19 3.3704 no . 3_557
H11 H19 3.3752 no . 3_657
H12 O16 2.9977 no . 3_657
H12 C17 3.2077 no . 3_657
H12 C18 3.4097 no . 3_657
H12 H7A 2.9069 no . 1_655
H12 H7A 3.5268 no . 3_557
H12 H7B 2.9969 no . 3_557
H12 H13 2.9885 no . 3_657
H12 H18 3.5617 no . 3_557
H12 H18 3.4220 no . 3_657
H13 C7 3.2857 no . 3_557
H13 C8 3.3745 no . 3_557
H13 C13 3.0505 no . 3_557
H13 H7A 3.0647 no . 1_655
H13 H7A 3.3005 no . 3_557
H13 H7B 2.7308 no . 3_557
H13 H12 2.9885 no . 3_657
H13 H13 2.6080 no . 3_557
H18 C10 3.2744 no . 3_557
H18 C11 3.0122 no . 3_557
H18 C12 3.2086 no . 3_557
H18 C22 3.3080 no . 1_455
H18 H1B 3.5889 no . 4_555
H18 H11 3.2592 no . 3_557
H18 H11 3.3701 no . 3_657
H18 H12 3.5617 no . 3_557
H18 H12 3.4220 no . 3_657
H18 H22 3.0373 no . 1_455
H19 N1 3.5653 no . 1_556
H19 N2 3.4392 no . 1_556
H19 C1 3.2221 no . 1_556
H19 C10 3.1628 no . 3_557
H19 C11 3.4402 no . 3_557
H19 C21 3.3480 no . 1_455
H19 H1A 3.0121 no . 1_556
H19 H1B 3.3345 no . 4_555
H19 H1C 2.7627 no . 1_556
H19 H6A 3.5046 no . 1_656
H19 H6B 3.0683 no . 1_656
H19 H10 2.8858 no . 3_557
H19 H11 3.3704 no . 3_557
H19 H11 3.3752 no . 3_657
H19 H21 3.0372 no . 1_455
H20 O15 3.4071 no . 4_555
H20 O16 3.5969 no . 4_555
H20 N2 3.0500 no . 1_656
H20 C1 3.1457 no . 1_556
H20 C15 3.4955 no . 4_555
H20 C22 3.3251 no . 4_555
H20 H1A 2.5606 no . 1_556
H20 H1B 3.2977 no . 4_555
H20 H1C 2.8565 no . 1_556
H20 H1C 3.4749 no . 1_656
H20 H22 2.9084 no . 4_555
H21 O15 2.8862 no . 4_655
H21 N1 3.1956 no . 4_655
H21 C1 3.1750 no . 4_655
H21 C19 3.3113 no . 1_655
H21 H1A 3.4969 no . 4_555
H21 H1B 3.4961 no . 4_555
H21 H1B 2.5851 no . 4_655
H21 H1C 3.4241 no . 1_656
H21 H1C 3.3458 no . 4_655
H21 H19 3.0372 no . 1_655
H22 O15 2.6303 no . 1_655
H22 C1 3.1842 no . 4_655
H22 C18 3.3385 no . 1_655
H22 H1A 3.4108 no . 4_555
H22 H1B 2.9990 no . 4_655
H22 H1C 2.6343 no . 4_655
H22 H18 3.0373 no . 1_655
H22 H20 2.9084 no . 4_554

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_database_code_depnum_ccdc_archive 'CCDC 987864'
