# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 1569797'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT430_9                   
;
PROBLEM: Short Inter D...A Contact  O4     ..  N15     ..       2.80 Ang.  
RESPONSE: The two molecules of the asymmetric unit are connected by 
carbonyl-carbonyl interactions which bring O(4) and N(15) into this 
close proximity. 
;
# end Validation Reply Form

_audit_creation_date             2017-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 O3'
_chemical_formula_sum            'C12 H8 N2 O3'
_chemical_formula_weight         228.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H8 N2 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6166(3)
_cell_length_b                   10.8878(9)
_cell_length_c                   16.1616(7)
_cell_angle_alpha                98.989(5)
_cell_angle_beta                 90.256(4)
_cell_angle_gamma                98.291(6)
_cell_volume                     965.60(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9150
_cell_measurement_theta_min      4.6190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -10 0.0230
0 -3 10 0.0131
-3 3 -4 0.0850
4 -2 0 0.0821
0 -6 -2 0.0114
0 0 -10 0.0196
0 7 1 0.0081

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.021
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0010 2.9952 -9.9914 0.8763 0.4346 0.1710
-0.0010 -2.9952 9.9914 -0.8763 -0.4346 -0.1710
-2.9990 2.9835 -3.9957 0.4829 0.3212 -0.7417
3.9988 -1.9806 -0.0012 -0.1861 -0.1393 1.0791
0.0075 -6.0013 -1.9972 0.3328 -0.8554 0.0517
0.0043 -0.0049 -9.9910 0.9479 0.0063 0.1790
-0.0082 7.0008 0.9980 -0.2619 0.9988 -0.0365

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_min         4.156
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  18.00   1.00   15.39    --  -42.56  57.00 120.00   84
  2  ω    -64.00  27.00   1.00   15.39    --  -42.56  57.00 -30.00   91
  3  ω      9.00  48.00   1.00   15.39    --   42.56 -99.00  30.00   39
  4  ω     44.00 109.00   1.00   61.53    --  106.63 -94.00 -30.00   65
  5  ω     55.00 130.00   1.00   61.53    --  106.63 -30.00-150.00   75
  6  ω     40.00 115.00   1.00   61.53    --  106.63 -61.00 -30.00   75
  7  ω     62.00 170.00   1.00   61.53    --  106.63  15.00  90.00  108
  8  ω    149.00 174.00   1.00   61.53    --  106.63  30.00 150.00   25
  9  ω     90.00 125.00   1.00   61.53    --  106.63  30.00 150.00   35
 10  ω     46.00 130.00   1.00   61.53    --  106.63 -30.00  90.00   84
 11  ω     77.00 104.00   1.00   61.53    --  106.63-113.00 134.00   27
 12  ω     43.00 125.00   1.00   61.53    --  106.63 -77.00 120.00   82
 13  ω     35.00  73.00   1.00   61.53    --  106.63-113.00 134.00   38
 14  ω     36.00 107.00   1.00   61.53    --  106.63-125.00 -60.00   71
 15  ω   -113.00 -18.00   1.00   15.39    --  -42.56 -57.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0584387000
_diffrn_orient_matrix_UB_12      -0.0239544000
_diffrn_orient_matrix_UB_13      -0.0948880000
_diffrn_orient_matrix_UB_21      0.0358927000
_diffrn_orient_matrix_UB_22      0.1428069000
_diffrn_orient_matrix_UB_23      -0.0006873000
_diffrn_orient_matrix_UB_31      0.2686762000
_diffrn_orient_matrix_UB_32      -0.0023612000
_diffrn_orient_matrix_UB_33      -0.0177946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3101
_reflns_number_total             3634
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.7340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7684(4) 0.67999(19) 0.43089(12) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.7699(4) 0.9021(2) 0.41862(14) 0.0234(5) Uani 1 1 d . . . . .
H2A H 0.7062 0.9453 0.4681 0.035 Uiso 1 1 calc GR . . . .
H2B H 0.7412 0.9426 0.3716 0.035 Uiso 1 1 calc GR . . . .
H2C H 0.9399 0.9040 0.4267 0.035 Uiso 1 1 calc GR . . . .
C3 C 0.4330(4) 0.74504(19) 0.35877(12) 0.0181(4) Uani 1 1 d . . . . .
C4 C 0.3088(3) 0.60789(19) 0.33795(12) 0.0164(4) Uani 1 1 d . . . . .
C5A C 0.3576(4) 0.38942(19) 0.35587(12) 0.0170(4) Uani 1 1 d . . . . .
C6 C 0.1562(4) 0.3135(2) 0.31524(13) 0.0197(4) Uani 1 1 d . . . . .
H6 H 0.0364 0.3473 0.2904 0.024 Uiso 1 1 calc R . . . .
C7 C 0.1442(4) 0.1851(2) 0.31394(13) 0.0219(4) Uani 1 1 d . . . . .
H7 H 0.0123 0.1315 0.2876 0.026 Uiso 1 1 calc R . . . .
C8 C 0.3246(4) 0.1336(2) 0.35101(13) 0.0225(4) Uani 1 1 d . . . . .
H8 H 0.3102 0.0470 0.3489 0.027 Uiso 1 1 calc R . . . .
C9 C 0.5244(4) 0.2102(2) 0.39082(13) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.6442 0.1760 0.4154 0.026 Uiso 1 1 calc R . . . .
C9A C 0.5413(4) 0.3399(2) 0.39308(12) 0.0183(4) Uani 1 1 d . . . . .
C10 C 0.7215(4) 0.4434(2) 0.42683(12) 0.0177(4) Uani 1 1 d . . . . .
H10 H 0.8639 0.4377 0.4546 0.021 Uiso 1 1 calc R . . . .
C10A C 0.6472(3) 0.55034(19) 0.41105(12) 0.0168(4) Uani 1 1 d . . . . .
N2 N 0.6511(3) 0.77088(16) 0.40254(10) 0.0180(4) Uani 1 1 d . . . . .
N5 N 0.4237(3) 0.52038(16) 0.36796(10) 0.0161(3) Uani 1 1 d . . . . .
O1 O 0.9595(3) 0.70790(14) 0.46946(9) 0.0209(3) Uani 1 1 d . . . . .
O3 O 0.3344(3) 0.82582(14) 0.33608(10) 0.0240(3) Uani 1 1 d . . . . .
O4 O 0.1226(2) 0.58239(14) 0.29760(9) 0.0196(3) Uani 1 1 d . . . . .
C11 C 0.2767(4) 0.6905(2) 0.09509(12) 0.0179(4) Uani 1 1 d . . . . .
C12 C 0.2970(4) 0.9159(2) 0.14135(14) 0.0245(5) Uani 1 1 d . . . . .
H12A H 0.4474 0.9233 0.1715 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.2016 0.9752 0.1695 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.3268 0.9327 0.0855 0.037 Uiso 1 1 calc GR . . . .
C13 C -0.0475(4) 0.7711(2) 0.17955(12) 0.0193(4) Uani 1 1 d . . . . .
C14 C -0.1773(3) 0.6361(2) 0.17919(12) 0.0182(4) Uani 1 1 d . . . . .
C15A C -0.1377(4) 0.4123(2) 0.12915(12) 0.0180(4) Uani 1 1 d . . . . .
C16 C -0.3354(4) 0.3440(2) 0.16161(13) 0.0220(4) Uani 1 1 d . . . . .
H16 H -0.4533 0.3836 0.1906 0.026 Uiso 1 1 calc R . . . .
C17 C -0.3474(4) 0.2147(2) 0.14863(14) 0.0245(5) Uani 1 1 d . . . . .
H17 H -0.4760 0.1663 0.1698 0.029 Uiso 1 1 calc R . . . .
C18 C -0.1708(4) 0.1542(2) 0.10445(14) 0.0256(5) Uani 1 1 d . . . . .
H18 H -0.1857 0.0670 0.0965 0.031 Uiso 1 1 calc R . . . .
C19 C 0.0251(4) 0.2227(2) 0.07257(13) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.1415 0.1826 0.0431 0.027 Uiso 1 1 calc R . . . .
C19A C 0.0433(4) 0.3541(2) 0.08586(12) 0.0189(4) Uani 1 1 d . . . . .
C20 C 0.2236(4) 0.4518(2) 0.06534(12) 0.0183(4) Uani 1 1 d . . . . .
H20 H 0.3639 0.4403 0.0367 0.022 Uiso 1 1 calc R . . . .
C20A C 0.1517(3) 0.5635(2) 0.09542(12) 0.0169(4) Uani 1 1 d . . . . .
N12 N 0.1672(3) 0.78787(17) 0.13774(11) 0.0196(4) Uani 1 1 d . . . . .
N15 N -0.0709(3) 0.54245(17) 0.13385(10) 0.0170(4) Uani 1 1 d . . . . .
O11 O 0.4659(3) 0.71206(14) 0.06023(9) 0.0209(3) Uani 1 1 d . . . . .
O13 O -0.1379(3) 0.85792(15) 0.21555(10) 0.0258(4) Uani 1 1 d . . . . .
O14 O -0.3616(3) 0.61763(15) 0.21618(9) 0.0217(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10A 1.462(3) . ?
C1 N2 1.396(3) . ?
C1 O1 1.214(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 N2 1.470(3) . ?
C3 C4 1.539(3) . ?
C3 N2 1.383(3) . ?
C3 O3 1.206(3) . ?
C4 N5 1.370(3) . ?
C4 O4 1.204(2) . ?
C5A C6 1.396(3) . ?
C5A C9A 1.404(3) . ?
C5A N5 1.403(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.401(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C9A 1.397(3) . ?
C9A C10 1.437(3) . ?
C10 H10 0.9300 . ?
C10 C10A 1.352(3) . ?
C10A N5 1.404(3) . ?
C11 C20A 1.459(3) . ?
C11 N12 1.393(3) . ?
C11 O11 1.215(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N12 1.469(3) . ?
C13 C14 1.542(3) . ?
C13 N12 1.388(3) . ?
C13 O13 1.208(3) . ?
C14 N15 1.371(3) . ?
C14 O14 1.205(2) . ?
C15A C16 1.397(3) . ?
C15A C19A 1.406(3) . ?
C15A N15 1.402(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.405(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9300 . ?
C19 C19A 1.402(3) . ?
C19A C20 1.438(3) . ?
C20 H20 0.9300 . ?
C20 C20A 1.355(3) . ?
C20A N15 1.404(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C10A 115.93(17) . . ?
O1 C1 C10A 122.54(18) . . ?
O1 C1 N2 121.54(19) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
N2 C3 C4 119.14(17) . . ?
O3 C3 C4 118.17(18) . . ?
O3 C3 N2 122.69(19) . . ?
N5 C4 C3 115.81(17) . . ?
O4 C4 C3 120.46(18) . . ?
O4 C4 N5 123.73(19) . . ?
C6 C5A C9A 122.51(19) . . ?
C6 C5A N5 130.64(19) . . ?
N5 C5A C9A 106.85(17) . . ?
C5A C6 H6 121.8 . . ?
C7 C6 C5A 116.47(19) . . ?
C7 C6 H6 121.8 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(2) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C9A 118.4(2) . . ?
C9A C9 H9 120.8 . . ?
C5A C9A C10 107.64(18) . . ?
C9 C9A C5A 119.78(19) . . ?
C9 C9A C10 132.6(2) . . ?
C9A C10 H10 126.1 . . ?
C10A C10 C9A 107.86(18) . . ?
C10A C10 H10 126.1 . . ?
C10 C10A C1 129.15(19) . . ?
C10 C10A N5 109.19(18) . . ?
N5 C10A C1 121.63(18) . . ?
C1 N2 C2 117.89(17) . . ?
C3 N2 C1 124.20(18) . . ?
C3 N2 C2 117.90(17) . . ?
C4 N5 C5A 128.11(17) . . ?
C4 N5 C10A 123.19(17) . . ?
C5A N5 C10A 108.46(16) . . ?
N12 C11 C20A 116.16(17) . . ?
O11 C11 C20A 122.83(19) . . ?
O11 C11 N12 121.00(19) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N12 C12 H12A 109.5 . . ?
N12 C12 H12B 109.5 . . ?
N12 C12 H12C 109.5 . . ?
N12 C13 C14 118.65(18) . . ?
O13 C13 C14 118.70(18) . . ?
O13 C13 N12 122.6(2) . . ?
N15 C14 C13 115.63(17) . . ?
O14 C14 C13 120.57(19) . . ?
O14 C14 N15 123.8(2) . . ?
C16 C15A C19A 122.4(2) . . ?
C16 C15A N15 130.48(19) . . ?
N15 C15A C19A 107.09(17) . . ?
C15A C16 H16 121.6 . . ?
C17 C16 C15A 116.8(2) . . ?
C17 C16 H16 121.6 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 121.9(2) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(2) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 120.9 . . ?
C18 C19 C19A 118.2(2) . . ?
C19A C19 H19 120.9 . . ?
C15A C19A C20 107.64(18) . . ?
C19 C19A C15A 119.70(19) . . ?
C19 C19A C20 132.6(2) . . ?
C19A C20 H20 126.2 . . ?
C20A C20 C19A 107.51(18) . . ?
C20A C20 H20 126.2 . . ?
C20 C20A C11 129.15(18) . . ?
C20 C20A N15 109.59(18) . . ?
N15 C20A C11 121.20(18) . . ?
C11 N12 C12 116.69(17) . . ?
C13 N12 C11 124.49(18) . . ?
C13 N12 C12 118.75(18) . . ?
C14 N15 C15A 127.39(17) . . ?
C14 N15 C20A 123.65(18) . . ?
C15A N15 C20A 108.16(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C10A N5 C4 3.3(3) . . . . ?
C1 C10A N5 C5A 178.10(16) . . . . ?
C3 C4 N5 C5A -177.23(17) . . . . ?
C3 C4 N5 C10A -3.5(3) . . . . ?
C4 C3 N2 C1 -0.9(3) . . . . ?
C4 C3 N2 C2 177.65(17) . . . . ?
C5A C6 C7 C8 -0.3(3) . . . . ?
C5A C9A C10 C10A 0.5(2) . . . . ?
C6 C5A C9A C9 -0.6(3) . . . . ?
C6 C5A C9A C10 178.52(18) . . . . ?
C6 C5A N5 C4 -3.9(3) . . . . ?
C6 C5A N5 C10A -178.4(2) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C9A 0.0(3) . . . . ?
C8 C9 C9A C5A 0.3(3) . . . . ?
C8 C9 C9A C10 -178.6(2) . . . . ?
C9 C9A C10 C10A 179.5(2) . . . . ?
C9A C5A C6 C7 0.6(3) . . . . ?
C9A C5A N5 C4 175.35(18) . . . . ?
C9A C5A N5 C10A 0.9(2) . . . . ?
C9A C10 C10A C1 -178.50(19) . . . . ?
C9A C10 C10A N5 0.0(2) . . . . ?
C10 C10A N5 C4 -175.36(17) . . . . ?
C10 C10A N5 C5A -0.5(2) . . . . ?
C10A C1 N2 C2 -178.06(17) . . . . ?
C10A C1 N2 C3 0.5(3) . . . . ?
N2 C1 C10A C10 176.78(19) . . . . ?
N2 C1 C10A N5 -1.6(3) . . . . ?
N2 C3 C4 N5 2.3(3) . . . . ?
N2 C3 C4 O4 -177.64(18) . . . . ?
N5 C5A C6 C7 179.81(19) . . . . ?
N5 C5A C9A C9 180.00(17) . . . . ?
N5 C5A C9A C10 -0.9(2) . . . . ?
O1 C1 C10A C10 -3.1(3) . . . . ?
O1 C1 C10A N5 178.60(18) . . . . ?
O1 C1 N2 C2 1.8(3) . . . . ?
O1 C1 N2 C3 -179.66(18) . . . . ?
O3 C3 C4 N5 -177.56(18) . . . . ?
O3 C3 C4 O4 2.5(3) . . . . ?
O3 C3 N2 C1 178.95(18) . . . . ?
O3 C3 N2 C2 -2.5(3) . . . . ?
O4 C4 N5 C5A 2.7(3) . . . . ?
O4 C4 N5 C10A 176.46(18) . . . . ?
C11 C20A N15 C14 -5.6(3) . . . . ?
C11 C20A N15 C15A -175.99(17) . . . . ?
C13 C14 N15 C15A 173.75(17) . . . . ?
C13 C14 N15 C20A 5.2(3) . . . . ?
C14 C13 N12 C11 -0.3(3) . . . . ?
C14 C13 N12 C12 -177.12(17) . . . . ?
C15A C16 C17 C18 -0.5(3) . . . . ?
C15A C19A C20 C20A 0.0(2) . . . . ?
C16 C15A C19A C19 1.4(3) . . . . ?
C16 C15A C19A C20 -177.03(18) . . . . ?
C16 C15A N15 C14 6.3(3) . . . . ?
C16 C15A N15 C20A 176.3(2) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C19A 0.3(3) . . . . ?
C18 C19 C19A C15A -1.2(3) . . . . ?
C18 C19 C19A C20 176.8(2) . . . . ?
C19 C19A C20 C20A -178.2(2) . . . . ?
C19A C15A C16 C17 -0.6(3) . . . . ?
C19A C15A N15 C14 -171.27(18) . . . . ?
C19A C15A N15 C20A -1.3(2) . . . . ?
C19A C20 C20A C11 176.25(19) . . . . ?
C19A C20 C20A N15 -0.8(2) . . . . ?
C20 C20A N15 C14 171.77(18) . . . . ?
C20 C20A N15 C15A 1.4(2) . . . . ?
C20A C11 N12 C12 177.12(17) . . . . ?
C20A C11 N12 C13 0.2(3) . . . . ?
N12 C11 C20A C20 -174.3(2) . . . . ?
N12 C11 C20A N15 2.5(3) . . . . ?
N12 C13 C14 N15 -2.3(3) . . . . ?
N12 C13 C14 O14 178.53(18) . . . . ?
N15 C15A C16 C17 -177.9(2) . . . . ?
N15 C15A C19A C19 179.27(18) . . . . ?
N15 C15A C19A C20 0.8(2) . . . . ?
O11 C11 C20A C20 5.5(3) . . . . ?
O11 C11 C20A N15 -177.71(18) . . . . ?
O11 C11 N12 C12 -2.7(3) . . . . ?
O11 C11 N12 C13 -179.53(18) . . . . ?
O13 C13 C14 N15 177.00(18) . . . . ?
O13 C13 C14 O14 -2.1(3) . . . . ?
O13 C13 N12 C11 -179.61(19) . . . . ?
O13 C13 N12 C12 3.6(3) . . . . ?
O14 C14 N15 C15A -7.1(3) . . . . ?
O14 C14 N15 C20A -175.65(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.809
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_slb_jones_3
_database_code_depnum_ccdc_archive 'CCDC 1569814'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2016-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 O3'
_chemical_formula_sum            'C12 H8 N2 O3'
_chemical_formula_weight         228.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H8N2O3
_chemical_oxdiff_usercomment     'Alan Jones 1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2887(8)
_cell_length_b                   7.9722(7)
_cell_length_c                   9.8335(10)
_cell_angle_alpha                95.529(8)
_cell_angle_beta                 103.372(9)
_cell_angle_gamma                115.216(10)
_cell_volume                     490.45(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5384
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2070
_cell_measurement_theta_min      4.0090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             236
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 3 -3 0.2540
-8 -3 3 0.2540
0 3 12 0.2988
0 -3 -12 0.2988
8 -10 -2 0.1599
-6 11 -4 0.2098
-8 7 9 0.2837
-4 9 -9 0.2001
-5 1 13 0.3591
5 -1 -13 0.3591

_exptl_crystal_preparation       'Fragment cut from larger crystal'
_exptl_crystal_size_max          0.777
_exptl_crystal_size_mid          0.586
_exptl_crystal_size_min          0.447
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.9418 3.0779 -2.9459 -0.5509 0.8134 0.3000
-7.9418 -3.0779 2.9459 0.5509 -0.8134 -0.3000
0.0088 2.9607 12.0422 -0.3260 0.4718 -0.8487
-0.0088 -2.9607 -12.0422 0.3260 -0.4718 0.8487
8.0450 -9.9938 -2.0889 -0.8006 -0.4596 0.3865
-6.0755 11.0385 -3.8988 0.8318 0.6113 0.0413
-8.0031 6.9463 9.0610 0.5307 0.2644 -0.8253
-4.0801 9.0632 -8.9189 0.7812 0.4804 0.4369
-4.9562 0.9154 13.0064 0.0436 -0.0617 -0.9755
4.9562 -0.9154 -13.0064 -0.0436 0.0617 0.9755

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16711
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.194
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   3.00   1.00    2.50    --  -16.31 -63.00 -83.15   86
  2  ω    -84.00   0.00   1.00    2.50    --  -16.31 -57.00-180.00   84
  3  ω    -84.00   0.00   1.00    2.50    --  -16.31 -57.00   0.00   84
  4  ω    -83.00   1.00   1.00    2.50    --  -16.31 -60.00 107.64   84
  5  ω    -51.00  33.00   1.00    2.50    --   16.39 -53.00-169.19   84
  6  ω      0.00  84.00   1.00    2.50    --   16.39  57.00 120.00   84
  7  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00-120.00   84
  8  ω    -53.00  36.00   1.00    2.50    --   16.39 -37.00 120.00   89
  9  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00 -60.00   84
 10  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00   0.00   84
 11  ω    -50.00  36.00   1.00    2.50    --   16.39 -65.00  86.52   86
 12  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00 120.00   84
 13  ω    -51.00  33.00   1.00    2.50    --   16.39 -58.00  40.91   84
 14  ω    -55.00  46.00   1.00    2.50    --   16.39 -19.00 150.00  101
 15  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00-180.00   84
 16  ω    -51.00  33.00   1.00    2.50    --   16.39 -57.00 150.00   84
 17  ω    -51.00  33.00   1.00    2.50    --   16.39 -56.00 -14.63   84
 18  ω    -53.00  14.00   1.00    2.50    --   16.39 -37.00  30.00   67
 19  ω    -53.00  36.00   1.00    2.50    --   16.39 -37.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0872321000
_diffrn_orient_matrix_UB_12      0.0163778000
_diffrn_orient_matrix_UB_13      -0.0310373000
_diffrn_orient_matrix_UB_21      0.0695790000
_diffrn_orient_matrix_UB_22      0.0989059000
_diffrn_orient_matrix_UB_23      0.0148119000
_diffrn_orient_matrix_UB_31      0.0168616000
_diffrn_orient_matrix_UB_32      -0.0109287000
_diffrn_orient_matrix_UB_33      -0.0678060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2079
_reflns_number_total             2245
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.1910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7168(2) 0.7431(2) 0.13320(14) 0.0311(4) Uani 1 1 d . . . . .
O2 O 0.7694(2) 0.49373(18) 0.66699(14) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.7822(2) 0.32253(18) 0.40085(14) 0.0264(3) Uani 1 1 d . . . . .
N1 N 0.7563(2) 0.5082(2) 0.23855(16) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.7564(2) 0.6030(2) 0.45945(16) 0.0216(4) Uani 1 1 d . . . . .
C1 C 0.7627(3) 0.3955(3) 0.1161(2) 0.0306(4) Uani 1 1 d . . . . .
H1A H 0.9044 0.4507 0.1082 0.046 Uiso 1 1 calc GR . . . .
H1B H 0.6659 0.3934 0.0303 0.046 Uiso 1 1 calc GR . . . .
H1C H 0.7222 0.2680 0.1288 0.046 Uiso 1 1 calc GR . . . .
C2 C 0.7360(3) 0.6729(3) 0.2362(2) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.7415(3) 0.7384(2) 0.38230(19) 0.0211(4) Uani 1 1 d . . . . .
C4 C 0.7343(3) 0.8932(2) 0.44069(19) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.7248 0.9802 0.3865 0.026 Uiso 1 1 calc R . . . .
C5 C 0.7414(3) 0.9225(2) 0.58878(19) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.7334(3) 1.0811(2) 0.6562(2) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.7255 1.1714 0.6052 0.029 Uiso 1 1 calc R . . . .
C7 C 0.7373(3) 1.1041(3) 0.7977(2) 0.0271(4) Uani 1 1 d . . . . .
H7 H 0.7297 1.2089 0.8411 0.033 Uiso 1 1 calc R . . . .
C8 C 0.7525(3) 0.9714(3) 0.8767(2) 0.0280(4) Uani 1 1 d . . . . .
H8 H 0.7564 0.9887 0.9724 0.034 Uiso 1 1 calc R . . . .
C9 C 0.7617(3) 0.8142(3) 0.8122(2) 0.0247(4) Uani 1 1 d . . . . .
H9 H 0.7718 0.7259 0.8649 0.030 Uiso 1 1 calc R . . . .
C10 C 0.7560(3) 0.7876(2) 0.66919(19) 0.0207(4) Uani 1 1 d . . . . .
C11 C 0.7622(3) 0.6158(2) 0.60380(19) 0.0203(4) Uani 1 1 d . . . . .
C12 C 0.7676(3) 0.4596(2) 0.37077(19) 0.0219(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.212(2) . ?
O2 C11 1.217(2) . ?
O3 C12 1.200(2) . ?
N1 C1 1.453(2) . ?
N1 C2 1.384(2) . ?
N1 C12 1.386(2) . ?
N2 C3 1.405(2) . ?
N2 C11 1.403(2) . ?
N2 C12 1.412(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.466(3) . ?
C3 C4 1.337(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.438(2) . ?
C5 C6 1.400(2) . ?
C5 C10 1.420(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.397(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(3) . ?
C10 C11 1.479(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 124.22(16) . . ?
C2 N1 C12 112.75(16) . . ?
C12 N1 C1 123.03(15) . . ?
C3 N2 C12 109.82(14) . . ?
C11 N2 C3 123.33(15) . . ?
C11 N2 C12 126.84(14) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 126.02(18) . . ?
O1 C2 C3 128.96(17) . . ?
N1 C2 C3 105.02(14) . . ?
N2 C3 C2 106.71(15) . . ?
C4 C3 N2 122.88(16) . . ?
C4 C3 C2 130.41(16) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.74(15) . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 121.57(15) . . ?
C6 C5 C10 118.87(16) . . ?
C10 C5 C4 119.57(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.31(16) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.66(17) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.90(17) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.32(16) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C11 121.50(16) . . ?
C9 C10 C5 119.95(16) . . ?
C9 C10 C11 118.55(15) . . ?
O2 C11 N2 121.97(17) . . ?
O2 C11 C10 124.05(17) . . ?
N2 C11 C10 113.98(14) . . ?
O3 C12 N1 126.22(17) . . ?
O3 C12 N2 128.13(16) . . ?
N1 C12 N2 105.65(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 N2 177.32(18) . . . . ?
O1 C2 C3 C4 -2.6(3) . . . . ?
N1 C2 C3 N2 -2.23(18) . . . . ?
N1 C2 C3 C4 177.87(18) . . . . ?
N2 C3 C4 C5 -0.2(3) . . . . ?
C1 N1 C2 O1 1.6(3) . . . . ?
C1 N1 C2 C3 -178.86(16) . . . . ?
C1 N1 C12 O3 -0.5(3) . . . . ?
C1 N1 C12 N2 179.98(15) . . . . ?
C2 N1 C12 O3 178.79(17) . . . . ?
C2 N1 C12 N2 -0.7(2) . . . . ?
C2 C3 C4 C5 179.69(17) . . . . ?
C3 N2 C11 O2 177.97(15) . . . . ?
C3 N2 C11 C10 -1.3(2) . . . . ?
C3 N2 C12 O3 179.71(17) . . . . ?
C3 N2 C12 N1 -0.82(19) . . . . ?
C3 C4 C5 C6 -179.69(16) . . . . ?
C3 C4 C5 C10 0.0(3) . . . . ?
C4 C5 C6 C7 179.00(16) . . . . ?
C4 C5 C10 C9 -179.62(15) . . . . ?
C4 C5 C10 C11 -0.5(3) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C5 C10 C11 O2 -178.13(16) . . . . ?
C5 C10 C11 N2 1.1(2) . . . . ?
C6 C5 C10 C9 0.1(3) . . . . ?
C6 C5 C10 C11 179.21(15) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
C8 C9 C10 C11 -178.88(16) . . . . ?
C9 C10 C11 O2 1.0(3) . . . . ?
C9 C10 C11 N2 -179.80(15) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C11 N2 C3 C2 -179.02(15) . . . . ?
C11 N2 C3 C4 0.9(3) . . . . ?
C11 N2 C12 O3 0.7(3) . . . . ?
C11 N2 C12 N1 -179.85(15) . . . . ?
C12 N1 C2 O1 -177.74(17) . . . . ?
C12 N1 C2 C3 1.8(2) . . . . ?
C12 N2 C3 C2 1.91(19) . . . . ?
C12 N2 C3 C4 -178.18(16) . . . . ?
C12 N2 C11 O2 -3.1(3) . . . . ?
C12 N2 C11 C10 177.63(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_exptl_crystal_mounting_method Loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_AMJ_001
_database_code_depnum_ccdc_archive 'CCDC 1569815'
_audit_update_record             
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.8352(11)
_cell_length_b                   7.7514(3)
_cell_length_c                   11.3697(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.229(4)
_cell_angle_gamma                90
_cell_volume                     2225.20(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8503
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7050
_cell_measurement_theta_min      3.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
36 -1 -1 0.0516
23 -8 -1 0.0649
6 6 -14 0.0598
9 10 3 0.0422
7 8 9 0.0576
-36 1 1 0.0586
-10 -10 2 0.0628
1 -1 -16 0.0502
-22 -9 1 0.0519
-10 -1 -14 0.0589
20 1 -15 0.0543
-21 8 7 0.0762
16 -9 4 0.0681
7 -8 9 0.0797
-18 9 2 0.0615
-9 -5 14 0.0919
-10 -10 7 0.0575

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
35.9808 -0.9960 -1.0036 -0.1302 -0.9949 0.0059
22.9981 -7.9935 -1.0037 0.4911 -0.7718 -0.3211
5.9933 5.9965 -13.9967 -0.0196 0.0255 1.0310
8.9797 9.9956 3.0005 -0.9261 -0.0741 0.3066
6.9814 7.9969 8.9991 -0.9651 -0.0899 -0.1086
-35.9808 0.9960 1.0036 0.1302 0.9949 -0.0059
-9.9810 -9.9954 1.9987 0.7618 0.0741 -0.5746
1.0067 -1.0003 -15.9972 0.6166 0.0414 0.8110
-21.9750 -8.9972 1.0002 0.7999 0.4255 -0.4739
-9.9876 -1.0012 -13.9965 0.6217 0.3304 0.7041
19.9925 1.0006 -14.9989 0.3027 -0.4446 0.8504
-21.0015 7.9940 7.0023 -0.7095 0.6845 -0.0006
16.0018 -8.9933 3.9959 0.4433 -0.6270 -0.6358
7.0038 -7.9945 8.9960 0.2562 -0.3902 -0.8568
-18.0028 8.9935 2.0032 -0.6350 0.6488 0.3142
-8.9929 -4.9974 13.9972 -0.0367 0.0751 -0.9842
-9.9828 -9.9951 6.9977 0.5909 0.0468 -0.8427

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.204
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  33.00   1.00   10.82    --   14.54 -57.00  30.00   26
  2  ω    -19.00  30.00   1.00   10.82    --  -13.60 -99.00 -90.00   49
  3  ω    -17.00  50.00   1.00   10.82    --   14.54  19.00  60.00   67
  4  ω     38.00  93.00   1.00   10.82    --   14.54  38.00 150.00   55
  5  ω     35.00 106.00   1.00   10.82    --   14.54 178.00 150.00   71
  6  ω     -8.00  93.00   1.00   10.82    --   14.54  38.00-120.00  101
  7  ω    -69.00  26.00   1.00   10.82    --   14.54 -77.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066866000
_diffrn_orient_matrix_UB_12      -0.0763776000
_diffrn_orient_matrix_UB_13      -0.0341863000
_diffrn_orient_matrix_UB_21      -0.0272850000
_diffrn_orient_matrix_UB_22      0.0187393000
_diffrn_orient_matrix_UB_23      -0.0054747000
_diffrn_orient_matrix_UB_31      -0.0000368000
_diffrn_orient_matrix_UB_32      0.0468024000
_diffrn_orient_matrix_UB_33      -0.0536257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3925
_reflns_number_total             4550
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+1.8760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C102(H102)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C111(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C105(H105), C106(H106), C107(H107), C108(H108)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C112(H11E,H11F,H11G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42930(7) 0.8057(3) 0.36807(16) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.38446(7) 0.8642(2) 0.52095(15) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.3976 0.8303 0.6050 0.021 Uiso 1 1 calc R . . . .
C3 C 0.41198(7) 1.0248(2) 0.49249(15) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.43726(7) 0.9889(3) 0.39974(16) 0.0214(4) Uani 1 1 d . . . . .
C5 C 0.46384(8) 1.1151(3) 0.34930(18) 0.0299(5) Uani 1 1 d . . . . .
H5 H 0.4811 1.0897 0.2875 0.036 Uiso 1 1 calc R . . . .
C6 C 0.46352(8) 1.2800(3) 0.3949(2) 0.0354(5) Uani 1 1 d . . . . .
H6 H 0.4806 1.3681 0.3626 0.042 Uiso 1 1 calc R . . . .
C7 C 0.43801(8) 1.3167(3) 0.4885(2) 0.0321(5) Uani 1 1 d . . . . .
H7 H 0.4385 1.4291 0.5175 0.039 Uiso 1 1 calc R . . . .
C8 C 0.41181(7) 1.1895(2) 0.53969(18) 0.0231(4) Uani 1 1 d . . . . .
H8 H 0.3950 1.2139 0.6025 0.028 Uiso 1 1 calc R . . . .
C9 C 0.29562(7) 0.8024(2) 0.55754(15) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.24285(7) 0.9591(2) 0.40642(15) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.29934(7) 0.9869(2) 0.39632(15) 0.0164(4) Uani 1 1 d . . . . .
H11A H 0.3054 0.9445 0.3201 0.020 Uiso 1 1 calc R . . . .
H11B H 0.3089 1.1079 0.4047 0.020 Uiso 1 1 calc R . . . .
C12 C 0.19640(7) 0.7894(2) 0.53907(17) 0.0213(4) Uani 1 1 d . . . . .
H12A H 0.1817 0.6939 0.4893 0.032 Uiso 1 1 calc GR . . . .
H12B H 0.1708 0.8808 0.5308 0.032 Uiso 1 1 calc GR . . . .
H12C H 0.2055 0.7529 0.6216 0.032 Uiso 1 1 calc GR . . . .
N1 N 0.32851(6) 0.88621(19) 0.49653(13) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.24382(6) 0.85103(19) 0.50196(13) 0.0168(3) Uani 1 1 d . . . . .
O1 O 0.44532(5) 0.7204(2) 0.29467(12) 0.0336(4) Uani 1 1 d . . . . .
O2 O 0.39871(5) 0.73478(16) 0.43963(12) 0.0218(3) Uani 1 1 d . . . . .
O3 O 0.30751(5) 0.70709(17) 0.64297(11) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.20336(5) 1.02152(18) 0.34350(12) 0.0259(3) Uani 1 1 d . . . . .
C101 C 0.06256(7) 0.2617(2) -0.07378(16) 0.0199(4) Uani 1 1 d . . . . .
C102 C 0.10766(7) 0.2602(2) 0.12666(15) 0.0166(4) Uani 1 1 d . . . . .
H102 H 0.0914 0.2953 0.1933 0.020 Uiso 1 1 calc R . . . .
C103 C 0.09081(6) 0.0786(2) 0.08753(15) 0.0157(4) Uani 1 1 d . . . . .
C104 C 0.06544(7) 0.0823(2) -0.03212(15) 0.0176(4) Uani 1 1 d . . . . .
C105 C 0.04564(7) -0.0665(3) -0.09414(16) 0.0217(4) Uani 1 1 d . . . . .
H105 H 0.0288 -0.0628 -0.1749 0.026 Uiso 1 1 calc R . . . .
C106 C 0.05203(7) -0.2200(2) -0.03067(18) 0.0233(4) Uani 1 1 d . . . . .
H106 H 0.0398 -0.3223 -0.0696 0.028 Uiso 1 1 calc R . . . .
C107 C 0.07667(7) -0.2232(2) 0.09148(17) 0.0211(4) Uani 1 1 d . . . . .
H107 H 0.0797 -0.3275 0.1329 0.025 Uiso 1 1 calc R . . . .
C108 C 0.09661(7) -0.0740(2) 0.15212(16) 0.0183(4) Uani 1 1 d . . . . .
H108 H 0.1132 -0.0766 0.2331 0.022 Uiso 1 1 calc R . . . .
C109 C 0.18844(7) 0.3855(2) 0.25219(15) 0.0180(4) Uani 1 1 d . . . . .
C110 C 0.25286(7) 0.2863(2) 0.15709(16) 0.0190(4) Uani 1 1 d . . . . .
C111 C 0.20064(7) 0.2108(2) 0.09351(16) 0.0183(4) Uani 1 1 d . . . . .
H11C H 0.1920 0.2450 0.0096 0.022 Uiso 1 1 calc R . . . .
H11D H 0.2011 0.0858 0.0985 0.022 Uiso 1 1 calc R . . . .
C112 C 0.28238(8) 0.4770(3) 0.33722(17) 0.0261(4) Uani 1 1 d . . . . .
H11E H 0.2765 0.5988 0.3265 0.039 Uiso 1 1 calc GR . . . .
H11F H 0.3170 0.4486 0.3251 0.039 Uiso 1 1 calc GR . . . .
H11G H 0.2797 0.4451 0.4173 0.039 Uiso 1 1 calc GR . . . .
N101 N 0.16358(6) 0.28379(19) 0.15913(13) 0.0169(3) Uani 1 1 d . . . . .
N102 N 0.24264(6) 0.38349(19) 0.25035(13) 0.0181(3) Uani 1 1 d . . . . .
O101 O 0.04326(5) 0.32332(19) -0.17060(11) 0.0270(3) Uani 1 1 d . . . . .
O102 O 0.08669(5) 0.36442(16) 0.02013(11) 0.0211(3) Uani 1 1 d . . . . .
O103 O 0.16878(5) 0.46455(17) 0.32378(11) 0.0245(3) Uani 1 1 d . . . . .
O104 O 0.29574(5) 0.26723(18) 0.13144(12) 0.0260(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.469(3) . ?
C1 O1 1.205(2) . ?
C1 O2 1.364(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.503(2) . ?
C2 N1 1.423(2) . ?
C2 O2 1.463(2) . ?
C3 C4 1.381(2) . ?
C3 C8 1.385(3) . ?
C4 C5 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.369(2) . ?
C9 N2 1.405(2) . ?
C9 O3 1.207(2) . ?
C10 C11 1.503(2) . ?
C10 N2 1.368(2) . ?
C10 O4 1.216(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.453(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N2 1.458(2) . ?
C101 C104 1.466(3) . ?
C101 O101 1.207(2) . ?
C101 O102 1.372(2) . ?
C102 H102 0.9800 . ?
C102 C103 1.512(2) . ?
C102 N101 1.425(2) . ?
C102 O102 1.461(2) . ?
C103 C104 1.380(2) . ?
C103 C108 1.384(2) . ?
C104 C105 1.391(3) . ?
C105 H105 0.9300 . ?
C105 C106 1.384(3) . ?
C106 H106 0.9300 . ?
C106 C107 1.400(3) . ?
C107 H107 0.9300 . ?
C107 C108 1.389(3) . ?
C108 H108 0.9300 . ?
C109 N101 1.366(2) . ?
C109 N102 1.405(2) . ?
C109 O103 1.213(2) . ?
C110 C111 1.507(2) . ?
C110 N102 1.371(2) . ?
C110 O104 1.213(2) . ?
C111 H11C 0.9700 . ?
C111 H11D 0.9700 . ?
C111 N101 1.448(2) . ?
C112 H11E 0.9600 . ?
C112 H11F 0.9600 . ?
C112 H11G 0.9600 . ?
C112 N102 1.458(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C4 130.52(19) . . ?
O1 C1 O2 121.28(19) . . ?
O2 C1 C4 108.19(15) . . ?
C3 C2 H2 110.5 . . ?
N1 C2 H2 110.5 . . ?
N1 C2 C3 111.48(14) . . ?
N1 C2 O2 109.87(14) . . ?
O2 C2 H2 110.5 . . ?
O2 C2 C3 103.78(13) . . ?
C4 C3 C2 108.63(16) . . ?
C4 C3 C8 121.49(17) . . ?
C8 C3 C2 129.76(16) . . ?
C3 C4 C1 108.53(16) . . ?
C3 C4 C5 121.96(19) . . ?
C5 C4 C1 129.50(18) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.06(19) . . ?
C6 C5 H5 121.5 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.13(19) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 116.69(18) . . ?
C3 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?
N1 C9 N2 106.20(14) . . ?
O3 C9 N1 128.22(17) . . ?
O3 C9 N2 125.57(16) . . ?
N2 C10 C11 107.07(14) . . ?
O4 C10 C11 127.26(16) . . ?
O4 C10 N2 125.66(16) . . ?
C10 C11 H11A 111.3 . . ?
C10 C11 H11B 111.3 . . ?
H11A C11 H11B 109.2 . . ?
N1 C11 C10 102.35(13) . . ?
N1 C11 H11A 111.3 . . ?
N1 C11 H11B 111.3 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
C2 N1 C11 123.63(14) . . ?
C9 N1 C2 123.91(15) . . ?
C9 N1 C11 112.19(14) . . ?
C9 N2 C12 124.10(15) . . ?
C10 N2 C9 112.14(14) . . ?
C10 N2 C12 123.74(15) . . ?
C1 O2 C2 110.82(14) . . ?
O101 C101 C104 130.80(18) . . ?
O101 C101 O102 120.79(17) . . ?
O102 C101 C104 108.41(14) . . ?
C103 C102 H102 110.0 . . ?
N101 C102 H102 110.0 . . ?
N101 C102 C103 114.12(14) . . ?
N101 C102 O102 108.73(13) . . ?
O102 C102 H102 110.0 . . ?
O102 C102 C103 103.75(13) . . ?
C104 C103 C102 108.55(15) . . ?
C104 C103 C108 121.08(16) . . ?
C108 C103 C102 130.36(16) . . ?
C103 C104 C101 108.61(16) . . ?
C103 C104 C105 121.98(17) . . ?
C105 C104 C101 129.38(17) . . ?
C104 C105 H105 121.4 . . ?
C106 C105 C104 117.27(17) . . ?
C106 C105 H105 121.4 . . ?
C105 C106 H106 119.6 . . ?
C105 C106 C107 120.78(17) . . ?
C107 C106 H106 119.6 . . ?
C106 C107 H107 119.3 . . ?
C108 C107 C106 121.37(17) . . ?
C108 C107 H107 119.3 . . ?
C103 C108 C107 117.49(16) . . ?
C103 C108 H108 121.3 . . ?
C107 C108 H108 121.3 . . ?
N101 C109 N102 106.79(14) . . ?
O103 C109 N101 128.04(17) . . ?
O103 C109 N102 125.17(16) . . ?
N102 C110 C111 106.55(15) . . ?
O104 C110 C111 127.41(16) . . ?
O104 C110 N102 126.04(17) . . ?
C110 C111 H11C 111.2 . . ?
C110 C111 H11D 111.2 . . ?
H11C C111 H11D 109.1 . . ?
N101 C111 C110 102.91(14) . . ?
N101 C111 H11C 111.2 . . ?
N101 C111 H11D 111.2 . . ?
H11E C112 H11F 109.5 . . ?
H11E C112 H11G 109.5 . . ?
H11F C112 H11G 109.5 . . ?
N102 C112 H11E 109.5 . . ?
N102 C112 H11F 109.5 . . ?
N102 C112 H11G 109.5 . . ?
C102 N101 C111 124.13(14) . . ?
C109 N101 C102 124.03(14) . . ?
C109 N101 C111 111.76(14) . . ?
C109 N102 C112 123.06(15) . . ?
C110 N102 C109 111.93(14) . . ?
C110 N102 C112 125.00(16) . . ?
C101 O102 C102 110.59(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C4 C5 C6 177.82(18) . . . . ?
C2 C3 C4 C1 -2.3(2) . . . . ?
C2 C3 C4 C5 176.53(16) . . . . ?
C2 C3 C8 C7 -175.08(18) . . . . ?
C3 C2 N1 C9 -150.28(16) . . . . ?
C3 C2 N1 C11 36.1(2) . . . . ?
C3 C2 O2 C1 -1.71(18) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C1 O2 C2 0.40(19) . . . . ?
C4 C3 C8 C7 0.4(3) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 -0.4(3) . . . . ?
C8 C3 C4 C1 -178.64(16) . . . . ?
C8 C3 C4 C5 0.2(3) . . . . ?
C10 C11 N1 C2 176.41(15) . . . . ?
C10 C11 N1 C9 2.11(18) . . . . ?
C11 C10 N2 C9 -0.15(19) . . . . ?
C11 C10 N2 C12 -178.30(15) . . . . ?
N1 C2 C3 C4 -115.76(16) . . . . ?
N1 C2 C3 C8 60.2(2) . . . . ?
N1 C2 O2 C1 117.60(15) . . . . ?
N1 C9 N2 C10 1.46(19) . . . . ?
N1 C9 N2 C12 179.61(15) . . . . ?
N2 C9 N1 C2 -176.53(15) . . . . ?
N2 C9 N1 C11 -2.25(19) . . . . ?
N2 C10 C11 N1 -1.13(17) . . . . ?
O1 C1 C4 C3 -178.23(19) . . . . ?
O1 C1 C4 C5 3.1(3) . . . . ?
O1 C1 O2 C2 179.92(16) . . . . ?
O2 C1 C4 C3 1.2(2) . . . . ?
O2 C1 C4 C5 -177.49(18) . . . . ?
O2 C2 C3 C4 2.45(18) . . . . ?
O2 C2 C3 C8 178.39(17) . . . . ?
O2 C2 N1 C9 95.24(18) . . . . ?
O2 C2 N1 C11 -78.39(19) . . . . ?
O3 C9 N1 C2 4.3(3) . . . . ?
O3 C9 N1 C11 178.62(17) . . . . ?
O3 C9 N2 C10 -179.38(17) . . . . ?
O3 C9 N2 C12 -1.2(3) . . . . ?
O4 C10 C11 N1 177.98(17) . . . . ?
O4 C10 N2 C9 -179.28(17) . . . . ?
O4 C10 N2 C12 2.6(3) . . . . ?
C101 C104 C105 C106 -177.20(17) . . . . ?
C102 C103 C104 C101 -2.40(19) . . . . ?
C102 C103 C104 C105 179.52(15) . . . . ?
C102 C103 C108 C107 179.69(17) . . . . ?
C103 C102 N101 C109 -141.91(16) . . . . ?
C103 C102 N101 C111 41.7(2) . . . . ?
C103 C102 O102 C101 -2.67(17) . . . . ?
C103 C104 C105 C106 0.4(3) . . . . ?
C104 C101 O102 C102 1.34(18) . . . . ?
C104 C103 C108 C107 0.9(2) . . . . ?
C104 C105 C106 C107 1.1(3) . . . . ?
C105 C106 C107 C108 -1.6(3) . . . . ?
C106 C107 C108 C103 0.6(3) . . . . ?
C108 C103 C104 C101 176.59(15) . . . . ?
C108 C103 C104 C105 -1.5(3) . . . . ?
C110 C111 N101 C102 175.13(15) . . . . ?
C110 C111 N101 C109 -1.65(18) . . . . ?
C111 C110 N102 C109 -2.33(19) . . . . ?
C111 C110 N102 C112 178.59(16) . . . . ?
N101 C102 C103 C104 -115.08(16) . . . . ?
N101 C102 C103 C108 66.1(2) . . . . ?
N101 C102 O102 C101 119.16(15) . . . . ?
N101 C109 N102 C110 1.31(19) . . . . ?
N101 C109 N102 C112 -179.58(15) . . . . ?
N102 C109 N101 C102 -176.45(15) . . . . ?
N102 C109 N101 C111 0.35(19) . . . . ?
N102 C110 C111 N101 2.35(18) . . . . ?
O101 C101 C104 C103 -178.85(18) . . . . ?
O101 C101 C104 C105 -1.0(3) . . . . ?
O101 C101 O102 C102 -179.04(16) . . . . ?
O102 C101 C104 C103 0.73(19) . . . . ?
O102 C101 C104 C105 178.62(17) . . . . ?
O102 C102 C103 C104 3.08(18) . . . . ?
O102 C102 C103 C108 -175.78(16) . . . . ?
O102 C102 N101 C109 102.82(18) . . . . ?
O102 C102 N101 C111 -73.58(19) . . . . ?
O103 C109 N101 C102 3.2(3) . . . . ?
O103 C109 N101 C111 -179.96(17) . . . . ?
O103 C109 N102 C110 -178.39(17) . . . . ?
O103 C109 N102 C112 0.7(3) . . . . ?
O104 C110 C111 N101 -177.16(18) . . . . ?
O104 C110 N102 C109 177.18(17) . . . . ?
O104 C110 N102 C112 -1.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.814
