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

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

data_psu-179-da-126
_database_code_depnum_ccdc_archive 'CCDC 1486439'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4'-Hydroxy-3'-(4-methoxybenzoyl)-1'-phenyl-2H,4H-spiro-[furo[3,2-c]chromene-3,2'-pyrrole]-2,4,5'(1'H)-trione
_chemical_name_common            ?
_chemical_melting_point          524-524
_chemical_formula_moiety         'C28 H17 N O8'
_chemical_formula_sum            'C28 H17 N O8'
_chemical_formula_weight         495.43

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'


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

_cell_length_a                   8.2673(11)
_cell_length_b                   18.169(3)
_cell_length_c                   14.955(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.962(13)
_cell_angle_gamma                90.00
_cell_volume                     2245.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4182
_cell_measurement_theta_min      3.5380
_cell_measurement_theta_max      28.1780


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12016
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         29.05
_reflns_number_total             5271
_reflns_number_gt                4053
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0682P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5271
_refine_ls_number_parameters     339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1333
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H 0.196(3) 0.5217(14) 0.5833(18) 0.091(8) Uiso 1 1 d . . .
O7 O -0.10593(14) 0.45365(6) 0.30045(7) 0.0452(3) Uani 1 1 d . . .
O8 O -0.05211(13) 0.42250(6) 0.16252(7) 0.0422(3) Uani 1 1 d . . .
O2 O 0.05126(14) 0.61959(6) 0.50532(7) 0.0481(3) Uani 1 1 d . . .
O1 O 0.24846(15) 0.49477(7) 0.54898(7) 0.0454(3) Uani 1 1 d . . .
O6 O 0.34408(13) 0.55671(6) 0.17134(7) 0.0450(3) Uani 1 1 d . . .
O3 O 0.45716(15) 0.44537(7) 0.28926(7) 0.0541(3) Uani 1 1 d . . .
N1 N 0.12561(15) 0.59899(7) 0.35966(8) 0.0369(3) Uani 1 1 d . . .
C20 C 0.21221(17) 0.51171(8) 0.16301(10) 0.0361(3) Uani 1 1 d . . .
C21 C 0.12847(17) 0.50466(8) 0.23821(9) 0.0333(3) Uani 1 1 d . . .
C22 C -0.01469(18) 0.46082(8) 0.23954(9) 0.0340(3) Uani 1 1 d . . .
C11 C 0.39732(18) 0.43620(9) 0.36264(10) 0.0378(3) Uani 1 1 d . . .
C28 C 0.17419(19) 0.47195(9) 0.08319(10) 0.0409(4) Uani 1 1 d . . .
C3 C 0.22421(17) 0.51860(8) 0.46590(9) 0.0342(3) Uani 1 1 d . . .
C12 C 0.44289(17) 0.37169(8) 0.41705(10) 0.0363(3) Uani 1 1 d . . .
O5 O 0.46477(15) 0.61610(8) 0.28789(9) 0.0622(4) Uani 1 1 d . . .
C19 C 0.36013(19) 0.57672(9) 0.26213(11) 0.0426(4) Uani 1 1 d . . .
C4 C 0.12214(17) 0.58522(8) 0.44922(10) 0.0366(3) Uani 1 1 d . . .
C5 C 0.03917(17) 0.65675(8) 0.31350(9) 0.0352(3) Uani 1 1 d . . .
C13 C 0.34942(18) 0.34214(9) 0.48312(10) 0.0424(4) Uani 1 1 d . . .
H13 H 0.2535 0.3653 0.4976 0.051 Uiso 1 1 calc R . .
C23 C 0.0429(2) 0.42445(9) 0.08850(10) 0.0417(4) Uani 1 1 d . . .
C2 C 0.28003(17) 0.49270(8) 0.38895(9) 0.0345(3) Uani 1 1 d . . .
C1 C 0.21751(17) 0.54313(8) 0.31358(9) 0.0344(3) Uani 1 1 d . . .
C14 C 0.3962(2) 0.27869(9) 0.52793(11) 0.0466(4) Uani 1 1 d . . .
H14 H 0.3317 0.2593 0.5719 0.056 Uiso 1 1 calc R . .
O4 O 0.59913(17) 0.18263(8) 0.54856(10) 0.0706(4) Uani 1 1 d . . .
C16 C 0.6323(2) 0.27271(11) 0.44016(13) 0.0597(5) Uani 1 1 d . . .
H16 H 0.7280 0.2493 0.4256 0.072 Uiso 1 1 calc R . .
C17 C 0.58449(19) 0.33476(10) 0.39561(12) 0.0490(4) Uani 1 1 d . . .
H17 H 0.6472 0.3529 0.3501 0.059 Uiso 1 1 calc R . .
C7 C -0.2082(2) 0.70909(9) 0.25652(11) 0.0473(4) Uani 1 1 d . . .
H7 H -0.3202 0.7072 0.2488 0.057 Uiso 1 1 calc R . .
C6 C -0.12738(19) 0.65314(9) 0.30158(10) 0.0412(4) Uani 1 1 d . . .
H6 H -0.1843 0.6134 0.3237 0.049 Uiso 1 1 calc R . .
C27 C 0.2629(2) 0.47271(11) 0.00509(11) 0.0533(5) Uani 1 1 d . . .
H27 H 0.3494 0.5050 -0.0002 0.064 Uiso 1 1 calc R . .
C15 C 0.5388(2) 0.24422(10) 0.50730(12) 0.0483(4) Uani 1 1 d . . .
C24 C 0.0014(2) 0.37674(11) 0.01960(12) 0.0583(5) Uani 1 1 d . . .
H24 H -0.0858 0.3448 0.0240 0.070 Uiso 1 1 calc R . .
C10 C 0.1236(2) 0.71559(9) 0.28022(14) 0.0538(5) Uani 1 1 d . . .
H10 H 0.2353 0.7182 0.2891 0.065 Uiso 1 1 calc R . .
C26 C 0.2214(3) 0.42542(14) -0.06356(11) 0.0661(6) Uani 1 1 d . . .
H26 H 0.2803 0.4256 -0.1154 0.079 Uiso 1 1 calc R . .
C8 C -0.1239(2) 0.76766(10) 0.22287(12) 0.0537(4) Uani 1 1 d . . .
H8 H -0.1791 0.8053 0.1927 0.064 Uiso 1 1 calc R . .
C18 C 0.5252(3) 0.15709(12) 0.62683(14) 0.0651(5) Uani 1 1 d . . .
H18A H 0.4157 0.1427 0.6123 0.098 Uiso 1 1 calc R . .
H18B H 0.5254 0.1957 0.6706 0.098 Uiso 1 1 calc R . .
H18C H 0.5843 0.1156 0.6505 0.098 Uiso 1 1 calc R . .
C9 C 0.0418(2) 0.77058(10) 0.23375(14) 0.0613(5) Uani 1 1 d . . .
H9 H 0.0988 0.8096 0.2098 0.074 Uiso 1 1 calc R . .
C25 C 0.0928(3) 0.37773(13) -0.05596(13) 0.0692(6) Uani 1 1 d . . .
H25 H 0.0672 0.3456 -0.1027 0.083 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O7 C22 1.2094(17) . ?
O8 C22 1.3722(17) . ?
O8 C23 1.3793(18) . ?
O2 C4 1.2128(17) . ?
O1 C3 1.3245(18) . ?
O1 H1 0.84(3) . ?
O6 C20 1.3650(19) . ?
O6 C19 1.4076(19) . ?
O3 C11 1.2304(18) . ?
N1 C4 1.3638(19) . ?
N1 C5 1.4334(19) . ?
N1 C1 1.4554(19) . ?
C20 C21 1.3467(19) . ?
C20 C28 1.421(2) . ?
C21 C22 1.427(2) . ?
C21 C1 1.498(2) . ?
C11 C12 1.469(2) . ?
C11 C2 1.475(2) . ?
C28 C23 1.391(2) . ?
C28 C27 1.401(2) . ?
C3 C2 1.340(2) . ?
C3 C4 1.492(2) . ?
C12 C13 1.383(2) . ?
C12 C17 1.396(2) . ?
O5 C19 1.1772(19) . ?
C19 C1 1.555(2) . ?
C5 C10 1.379(2) . ?
C5 C6 1.384(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C23 C24 1.381(2) . ?
C2 C1 1.529(2) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9300 . ?
O4 C15 1.364(2) . ?
O4 C18 1.417(2) . ?
C16 C17 1.361(2) . ?
C16 C15 1.388(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C7 C8 1.377(3) . ?
C7 C6 1.379(2) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C27 C26 1.373(3) . ?
C27 H27 0.9300 . ?
C24 C25 1.381(3) . ?
C24 H24 0.9300 . ?
C10 C9 1.380(3) . ?
C10 H10 0.9300 . ?
C26 C25 1.379(3) . ?
C26 H26 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C9 H9 0.9300 . ?
C25 H25 0.9300 . ?

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
C22 O8 C23 122.85(12) . . ?
C3 O1 H1 108.6(18) . . ?
C20 O6 C19 106.94(11) . . ?
C4 N1 C5 125.47(12) . . ?
C4 N1 C1 111.47(12) . . ?
C5 N1 C1 122.84(12) . . ?
C21 C20 O6 114.36(13) . . ?
C21 C20 C28 123.22(14) . . ?
O6 C20 C28 122.28(13) . . ?
C20 C21 C22 120.99(13) . . ?
C20 C21 C1 109.30(13) . . ?
C22 C21 C1 129.51(13) . . ?
O7 C22 O8 116.68(13) . . ?
O7 C22 C21 127.55(14) . . ?
O8 C22 C21 115.76(12) . . ?
O3 C11 C12 119.93(13) . . ?
O3 C11 C2 115.58(14) . . ?
C12 C11 C2 124.49(13) . . ?
C23 C28 C27 119.07(15) . . ?
C23 C28 C20 114.70(13) . . ?
C27 C28 C20 126.04(16) . . ?
O1 C3 C2 130.20(14) . . ?
O1 C3 C4 119.25(13) . . ?
C2 C3 C4 110.54(13) . . ?
C13 C12 C17 118.08(14) . . ?
C13 C12 C11 124.51(13) . . ?
C17 C12 C11 117.23(14) . . ?
O5 C19 O6 121.11(15) . . ?
O5 C19 C1 129.64(15) . . ?
O6 C19 C1 109.14(12) . . ?
O2 C4 N1 127.72(14) . . ?
O2 C4 C3 125.89(14) . . ?
N1 C4 C3 106.40(12) . . ?
C10 C5 C6 120.25(15) . . ?
C10 C5 N1 119.42(14) . . ?
C6 C5 N1 120.32(13) . . ?
C14 C13 C12 121.07(14) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
O8 C23 C24 116.70(16) . . ?
O8 C23 C28 121.91(14) . . ?
C24 C23 C28 121.40(16) . . ?
C3 C2 C11 136.27(14) . . ?
C3 C2 C1 107.76(12) . . ?
C11 C2 C1 115.42(12) . . ?
N1 C1 C21 115.51(12) . . ?
N1 C1 C2 103.75(11) . . ?
C21 C1 C2 114.84(12) . . ?
N1 C1 C19 112.18(12) . . ?
C21 C1 C19 99.92(11) . . ?
C2 C1 C19 110.93(12) . . ?
C15 C14 C13 119.84(15) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C15 O4 C18 118.75(15) . . ?
C17 C16 C15 120.21(16) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 121.16(16) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?
C8 C7 C6 120.37(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C6 C5 119.40(15) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C26 C27 C28 119.50(19) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
O4 C15 C14 124.98(16) . . ?
O4 C15 C16 115.43(15) . . ?
C14 C15 C16 119.59(16) . . ?
C23 C24 C25 118.28(19) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C5 C10 C9 119.84(16) . . ?
C5 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C27 C26 C25 120.35(18) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C9 C8 C7 120.08(16) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C9 C10 120.03(17) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C26 C25 C24 121.37(18) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 O6 C20 C21 5.75(18) . . . . ?
C19 O6 C20 C28 -170.13(14) . . . . ?
O6 C20 C21 C22 178.51(13) . . . . ?
C28 C20 C21 C22 -5.7(2) . . . . ?
O6 C20 C21 C1 -6.12(18) . . . . ?
C28 C20 C21 C1 169.72(13) . . . . ?
C23 O8 C22 O7 -178.72(13) . . . . ?
C23 O8 C22 C21 1.22(19) . . . . ?
C20 C21 C22 O7 -175.00(15) . . . . ?
C1 C21 C22 O7 10.7(3) . . . . ?
C20 C21 C22 O8 5.1(2) . . . . ?
C1 C21 C22 O8 -169.28(13) . . . . ?
C21 C20 C28 C23 -0.2(2) . . . . ?
O6 C20 C28 C23 175.32(14) . . . . ?
C21 C20 C28 C27 -175.11(16) . . . . ?
O6 C20 C28 C27 0.4(2) . . . . ?
O3 C11 C12 C13 -157.20(15) . . . . ?
C2 C11 C12 C13 22.0(2) . . . . ?
O3 C11 C12 C17 17.8(2) . . . . ?
C2 C11 C12 C17 -163.00(15) . . . . ?
C20 O6 C19 O5 -179.54(16) . . . . ?
C20 O6 C19 C1 -2.99(16) . . . . ?
C5 N1 C4 O2 -2.4(2) . . . . ?
C1 N1 C4 O2 -177.07(14) . . . . ?
C5 N1 C4 C3 177.73(13) . . . . ?
C1 N1 C4 C3 3.03(16) . . . . ?
O1 C3 C4 O2 -3.1(2) . . . . ?
C2 C3 C4 O2 177.78(15) . . . . ?
O1 C3 C4 N1 176.81(13) . . . . ?
C2 C3 C4 N1 -2.31(17) . . . . ?
C4 N1 C5 C10 109.74(18) . . . . ?
C1 N1 C5 C10 -76.12(19) . . . . ?
C4 N1 C5 C6 -70.96(19) . . . . ?
C1 N1 C5 C6 103.18(17) . . . . ?
C17 C12 C13 C14 1.3(2) . . . . ?
C11 C12 C13 C14 176.18(15) . . . . ?
C22 O8 C23 C24 172.65(14) . . . . ?
C22 O8 C23 C28 -7.3(2) . . . . ?
C27 C28 C23 O8 -178.18(14) . . . . ?
C20 C28 C23 O8 6.5(2) . . . . ?
C27 C28 C23 C24 1.9(2) . . . . ?
C20 C28 C23 C24 -173.38(15) . . . . ?
O1 C3 C2 C11 -7.6(3) . . . . ?
C4 C3 C2 C11 171.38(16) . . . . ?
O1 C3 C2 C1 -178.31(15) . . . . ?
C4 C3 C2 C1 0.68(16) . . . . ?
O3 C11 C2 C3 -155.49(18) . . . . ?
C12 C11 C2 C3 25.3(3) . . . . ?
O3 C11 C2 C1 14.7(2) . . . . ?
C12 C11 C2 C1 -164.56(13) . . . . ?
C4 N1 C1 C21 123.98(14) . . . . ?
C5 N1 C1 C21 -50.89(19) . . . . ?
C4 N1 C1 C2 -2.60(15) . . . . ?
C5 N1 C1 C2 -177.47(12) . . . . ?
C4 N1 C1 C19 -122.40(14) . . . . ?
C5 N1 C1 C19 62.73(17) . . . . ?
C20 C21 C1 N1 124.17(14) . . . . ?
C22 C21 C1 N1 -61.0(2) . . . . ?
C20 C21 C1 C2 -115.09(14) . . . . ?
C22 C21 C1 C2 59.76(19) . . . . ?
C20 C21 C1 C19 3.63(15) . . . . ?
C22 C21 C1 C19 178.49(15) . . . . ?
C3 C2 C1 N1 1.07(15) . . . . ?
C11 C2 C1 N1 -171.82(12) . . . . ?
C3 C2 C1 C21 -125.93(13) . . . . ?
C11 C2 C1 C21 61.18(17) . . . . ?
C3 C2 C1 C19 121.71(14) . . . . ?
C11 C2 C1 C19 -51.18(17) . . . . ?
O5 C19 C1 N1 52.9(2) . . . . ?
O6 C19 C1 N1 -123.25(13) . . . . ?
O5 C19 C1 C21 175.83(19) . . . . ?
O6 C19 C1 C21 -0.34(15) . . . . ?
O5 C19 C1 C2 -62.6(2) . . . . ?
O6 C19 C1 C2 121.24(13) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C15 C16 C17 C12 1.0(3) . . . . ?
C13 C12 C17 C16 -2.0(3) . . . . ?
C11 C12 C17 C16 -177.31(17) . . . . ?
C8 C7 C6 C5 0.7(2) . . . . ?
C10 C5 C6 C7 -0.3(2) . . . . ?
N1 C5 C6 C7 -179.62(14) . . . . ?
C23 C28 C27 C26 -1.7(2) . . . . ?
C20 C28 C27 C26 173.04(16) . . . . ?
C18 O4 C15 C14 -9.7(3) . . . . ?
C18 O4 C15 C16 170.01(18) . . . . ?
C13 C14 C15 O4 178.21(16) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C17 C16 C15 O4 -178.98(18) . . . . ?
C17 C16 C15 C14 0.7(3) . . . . ?
O8 C23 C24 C25 179.33(16) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
N1 C5 C10 C9 178.40(16) . . . . ?
C28 C27 C26 C25 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C5 C10 C9 C8 1.8(3) . . . . ?
C27 C26 C25 C24 0.9(3) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.880
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.043
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_psu-339-da-209
_database_code_depnum_ccdc_archive 'CCDC 1486440'
_audit_update_record             
;
2016-06-18 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;
_audit_creation_date             2016-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
3'-Benzoyl-4'-hydroxy-5-methyl-1'-(4-tolyl)-2H-spiro?[furo?[3,2-c]quinoline-3,2'-pyrrole]-2,4,5'(1'H,5H)-trione
_chemical_formula_moiety         'C29 H20 N2 O6, C2 H3 N'
_chemical_formula_sum            'C31 H23 N3 O6'
_chemical_formula_weight         533.52
_chemical_melting_point          530-532
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                   10.0480(16)
_cell_length_b                   10.5278(12)
_cell_length_c                   13.3170(16)
_cell_angle_alpha                83.352(10)
_cell_angle_beta                 74.653(13)
_cell_angle_gamma                89.492(11)
_cell_volume                     1349.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3383
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.7140
_cell_measurement_theta_min      3.8190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             556
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12089
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.233
_diffrn_reflns_theta_min         2.834
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   31.00   75.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   38.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   26.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -99.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -85.00    4.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -38.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   40.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541   57.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -94.00  -58.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -38.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega -106.00  -36.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541 -178.0000 -150.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0299994000
_diffrn_orient_matrix_UB_12      0.0011888000
_diffrn_orient_matrix_UB_13      -0.0426841000
_diffrn_orient_matrix_UB_21      -0.0665709000
_diffrn_orient_matrix_UB_22      0.0033047000
_diffrn_orient_matrix_UB_23      0.0348596000
_diffrn_orient_matrix_UB_31      0.0054392000
_diffrn_orient_matrix_UB_32      0.0677569000
_diffrn_orient_matrix_UB_33      -0.0075017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4550
_reflns_number_total             6306
_reflns_odcompleteness_completeness 99.73
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6306
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.035
_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)+(0.0650P)²+0.1775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1455
_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. Rigid bond restraints
 N1SA, N1SB, C1SB, C2SB, C1SA, C2SA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Uiso/Uaniso restraints and constraints
N1SA \\sim N1SB \\sim C1SB \\sim C2SB \\sim C1SA \\sim C2SA: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Same fragment restrains
{N1SA, C1SA, C2SA} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1SB, C1SB, C2SB}
5. Others
 Fixed Sof: N1SA(0.5) C1SA(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C2SA(0.5)
 N1SB(0.5) C1SB(0.5) H1SD(0.5) H1SE(0.5) H1SF(0.5) C2SB(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28)
6.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C1SA(H1SA,H1SB,H1SC), C1SB(H1SD,
 H1SE,H1SF)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.50061(12) 1.15678(9) 0.09013(9) 0.0486(3) Uani 1 1 d . . . . .
H1 H 0.533(2) 1.182(2) 0.013(2) 0.097(7) Uiso 1 1 d . . . . .
O2 O 0.72395(11) 1.05413(10) -0.05438(8) 0.0482(3) Uani 1 1 d . . . . .
O3 O 0.81103(15) 0.95631(12) 0.27246(11) 0.0694(4) Uani 1 1 d . . . . .
O4 O 0.73560(12) 0.75301(10) 0.32355(9) 0.0518(3) Uani 1 1 d . . . . .
O5 O 0.45732(12) 0.70715(10) 0.10042(9) 0.0535(3) Uani 1 1 d . . . . .
O6 O 0.49575(15) 0.91692(12) 0.38310(9) 0.0690(4) Uani 1 1 d . . . . .
N1 N 0.72537(13) 0.89679(11) 0.08132(10) 0.0426(3) Uani 1 1 d . . . . .
N2 N 0.47932(14) 0.53482(11) 0.21563(11) 0.0464(3) Uani 1 1 d . . . . .
C1 C 0.67953(15) 1.00324(12) 0.03470(11) 0.0373(3) Uani 1 1 d . . . . .
C2 C 0.56132(15) 1.04937(12) 0.11477(11) 0.0377(3) Uani 1 1 d . . . . .
C3 C 0.53799(16) 0.97166(13) 0.20524(11) 0.0399(3) Uani 1 1 d . . . . .
C4 C 0.64445(16) 0.86681(13) 0.19016(11) 0.0408(3) Uani 1 1 d . . . . .
C5 C 0.73900(18) 0.87173(15) 0.26519(13) 0.0498(4) Uani 1 1 d . . . . .
C6 C 0.64751(16) 0.67488(14) 0.29355(12) 0.0429(3) Uani 1 1 d . . . . .
C7 C 0.59258(15) 0.73116(13) 0.21810(11) 0.0407(3) Uani 1 1 d . . . . .
C8 C 0.50577(16) 0.66173(13) 0.17293(12) 0.0416(3) Uani 1 1 d . . . . .
C9 C 0.53282(16) 0.47705(14) 0.29613(12) 0.0466(4) Uani 1 1 d . . . . .
C10 C 0.62100(17) 0.54568(14) 0.33749(12) 0.0461(4) Uani 1 1 d . . . . .
C11 C 0.67841(19) 0.48668(17) 0.41599(13) 0.0577(4) Uani 1 1 d . . . . .
H11 H 0.7363 0.5328 0.4433 0.069 Uiso 1 1 calc R . . . .
C12 C 0.6480(2) 0.36024(19) 0.45163(16) 0.0724(6) Uani 1 1 d . . . . .
H12 H 0.6862 0.3197 0.5030 0.087 Uiso 1 1 calc R . . . .
C13 C 0.5606(2) 0.29268(18) 0.41143(17) 0.0758(6) Uani 1 1 d . . . . .
H13 H 0.5404 0.2070 0.4368 0.091 Uiso 1 1 calc R . . . .
C14 C 0.5033(2) 0.34836(16) 0.33549(16) 0.0647(5) Uani 1 1 d . . . . .
H14 H 0.4447 0.3008 0.3099 0.078 Uiso 1 1 calc R . . . .
C15 C 0.3942(2) 0.45865(17) 0.17008(18) 0.0702(6) Uani 1 1 d . . . . .
H15A H 0.3154 0.4237 0.2240 0.105 Uiso 1 1 calc GR . . . .
H15B H 0.4475 0.3903 0.1390 0.105 Uiso 1 1 calc GR . . . .
H15C H 0.3638 0.5120 0.1173 0.105 Uiso 1 1 calc GR . . . .
C16 C 0.45246(17) 0.97585(13) 0.31357(12) 0.0459(4) Uani 1 1 d . . . . .
C17 C 0.32096(17) 1.04441(14) 0.34005(12) 0.0460(4) Uani 1 1 d . . . . .
C18 C 0.24201(19) 1.07195(19) 0.26998(14) 0.0626(5) Uani 1 1 d . . . . .
H18 H 0.2743 1.0527 0.2014 0.075 Uiso 1 1 calc R . . . .
C19 C 0.1153(2) 1.1280(3) 0.30147(18) 0.0868(7) Uani 1 1 d . . . . .
H19 H 0.0606 1.1429 0.2551 0.104 Uiso 1 1 calc R . . . .
C20 C 0.0701(3) 1.1618(3) 0.4012(2) 0.1093(10) Uani 1 1 d . . . . .
H20 H -0.0138 1.2023 0.4215 0.131 Uiso 1 1 calc R . . . .
C21 C 0.1489(3) 1.1359(3) 0.47106(19) 0.1069(10) Uani 1 1 d . . . . .
H21 H 0.1184 1.1596 0.5384 0.128 Uiso 1 1 calc R . . . .
C22 C 0.2719(2) 1.0754(2) 0.44179(14) 0.0681(5) Uani 1 1 d . . . . .
H22 H 0.3229 1.0550 0.4902 0.082 Uiso 1 1 calc R . . . .
C23 C 0.83317(16) 0.81754(14) 0.02992(12) 0.0437(4) Uani 1 1 d . . . . .
C24 C 0.96404(19) 0.82697(18) 0.04263(18) 0.0683(5) Uani 1 1 d . . . . .
H24 H 0.9833 0.8840 0.0856 0.082 Uiso 1 1 calc R . . . .
C25 C 1.06677(19) 0.7511(2) -0.0089(2) 0.0797(7) Uani 1 1 d . . . . .
H25 H 1.1547 0.7570 0.0007 0.096 Uiso 1 1 calc R . . . .
C26 C 1.0423(2) 0.66723(18) -0.07409(17) 0.0658(5) Uani 1 1 d . . . . .
C27 C 0.9108(2) 0.6582(2) -0.08420(18) 0.0756(6) Uani 1 1 d . . . . .
H27 H 0.8915 0.6010 -0.1270 0.091 Uiso 1 1 calc R . . . .
C28 C 0.8059(2) 0.73184(19) -0.03245(15) 0.0647(5) Uani 1 1 d . . . . .
H28 H 0.7171 0.7232 -0.0400 0.078 Uiso 1 1 calc R . . . .
C29 C 1.1561(3) 0.5895(3) -0.1345(2) 0.1014(9) Uani 1 1 d . . . . .
H29A H 1.1789 0.6221 -0.2075 0.152 Uiso 1 1 calc GR . . . .
H29B H 1.1257 0.5018 -0.1259 0.152 Uiso 1 1 calc GR . . . .
H29C H 1.2361 0.5952 -0.1086 0.152 Uiso 1 1 calc GR . . . .
N1SA N 0.1293(15) 0.5474(13) 0.3909(9) 0.256(6) Uani 0.5 1 d D U P A 1
C1SA C 0.1077(18) 0.7308(14) 0.2621(13) 0.165(7) Uani 0.5 1 d D U P A 1
H1SA H 0.0398 0.7051 0.2291 0.248 Uiso 0.5 1 calc GR . P A 1
H1SB H 0.1951 0.7451 0.2107 0.248 Uiso 0.5 1 calc GR . P A 1
H1SC H 0.0798 0.8083 0.2925 0.248 Uiso 0.5 1 calc GR . P A 1
C2SA C 0.120(2) 0.6348(15) 0.3403(11) 0.159(5) Uani 0.5 1 d D U P A 1
N1SB N 0.0491(8) 0.5372(7) 0.3141(10) 0.204(4) Uani 0.5 1 d D U P B 2
C1SB C 0.1412(15) 0.7627(9) 0.2911(10) 0.101(3) Uani 0.5 1 d D U P B 2
H1SD H 0.1791 0.7757 0.3482 0.151 Uiso 0.5 1 calc GR . P B 2
H1SE H 0.0652 0.8188 0.2913 0.151 Uiso 0.5 1 calc GR . P B 2
H1SF H 0.2110 0.7809 0.2260 0.151 Uiso 0.5 1 calc GR . P B 2
C2SB C 0.0949(12) 0.6357(8) 0.3021(9) 0.118(4) Uani 0.5 1 d D U P B 2


_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 H1 1.00(3) . ?
O1 C2 1.3290(17) . ?
O2 C1 1.2126(17) . ?
O3 C5 1.181(2) . ?
O4 C5 1.3889(18) . ?
O4 C6 1.3768(19) . ?
O5 C8 1.2393(18) . ?
O6 C16 1.2276(18) . ?
N1 C1 1.3544(18) . ?
N1 C4 1.4616(19) . ?
N1 C23 1.4359(19) . ?
N2 C8 1.3890(18) . ?
N2 C9 1.399(2) . ?
N2 C15 1.464(2) . ?
C1 C2 1.491(2) . ?
C2 C3 1.3421(19) . ?
C3 C4 1.523(2) . ?
C3 C16 1.476(2) . ?
C4 C5 1.555(2) . ?
C4 C7 1.4957(19) . ?
C6 C7 1.347(2) . ?
C6 C10 1.415(2) . ?
C7 C8 1.431(2) . ?
C9 C10 1.404(2) . ?
C9 C14 1.399(2) . ?
C10 C11 1.405(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.479(2) . ?
C17 C18 1.382(2) . ?
C17 C22 1.390(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.375(2) . ?
C23 C28 1.370(2) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.373(3) . ?
C26 C27 1.368(3) . ?
C26 C29 1.508(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.383(3) . ?
C28 H28 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
N1SA C2SA 1.094(12) . ?
C1SA H1SA 0.9600 . ?
C1SA H1SB 0.9600 . ?
C1SA H1SC 0.9600 . ?
C1SA C2SA 1.394(13) . ?
N1SB C2SB 1.116(9) . ?
C1SB H1SD 0.9600 . ?
C1SB H1SE 0.9600 . ?
C1SB H1SF 0.9600 . ?
C1SB C2SB 1.398(10) . ?

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 O1 H1 109.0(14) . . ?
C6 O4 C5 107.13(11) . . ?
C1 N1 C4 111.27(12) . . ?
C1 N1 C23 125.09(12) . . ?
C23 N1 C4 123.52(11) . . ?
C8 N2 C9 123.56(14) . . ?
C8 N2 C15 116.93(13) . . ?
C9 N2 C15 119.48(13) . . ?
O2 C1 N1 128.06(14) . . ?
O2 C1 C2 125.13(13) . . ?
N1 C1 C2 106.81(12) . . ?
O1 C2 C1 119.02(12) . . ?
O1 C2 C3 130.60(15) . . ?
C3 C2 C1 110.33(12) . . ?
C2 C3 C4 107.76(13) . . ?
C2 C3 C16 135.59(14) . . ?
C16 C3 C4 115.85(12) . . ?
N1 C4 C3 103.82(11) . . ?
N1 C4 C5 110.02(12) . . ?
N1 C4 C7 114.09(12) . . ?
C3 C4 C5 111.11(12) . . ?
C7 C4 C3 117.57(13) . . ?
C7 C4 C5 100.32(11) . . ?
O3 C5 O4 121.49(15) . . ?
O3 C5 C4 129.07(14) . . ?
O4 C5 C4 109.34(13) . . ?
O4 C6 C10 121.97(13) . . ?
C7 C6 O4 114.32(12) . . ?
C7 C6 C10 123.70(15) . . ?
C6 C7 C4 108.88(13) . . ?
C6 C7 C8 121.78(13) . . ?
C8 C7 C4 129.25(12) . . ?
O5 C8 N2 120.68(14) . . ?
O5 C8 C7 124.49(13) . . ?
N2 C8 C7 114.82(13) . . ?
N2 C9 C10 120.83(13) . . ?
N2 C9 C14 120.97(16) . . ?
C14 C9 C10 118.18(15) . . ?
C9 C10 C6 115.26(14) . . ?
C9 C10 C11 120.93(14) . . ?
C11 C10 C6 123.81(16) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.05(19) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.12(17) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.73(17) . . ?
C14 C13 H13 119.1 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 C3 116.05(15) . . ?
O6 C16 C17 120.35(14) . . ?
C3 C16 C17 123.59(13) . . ?
C18 C17 C16 122.78(15) . . ?
C18 C17 C22 119.13(17) . . ?
C22 C17 C16 117.99(15) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.19(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.28(19) . . ?
C21 C22 H22 119.9 . . ?
C24 C23 N1 120.52(15) . . ?
C28 C23 N1 119.91(14) . . ?
C28 C23 C24 119.57(16) . . ?
C23 C24 H24 120.2 . . ?
C23 C24 C25 119.52(19) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.73(19) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 C29 121.6(2) . . ?
C27 C26 C25 117.64(18) . . ?
C27 C26 C29 120.7(2) . . ?
C26 C27 H27 119.1 . . ?
C26 C27 C28 121.7(2) . . ?
C28 C27 H27 119.1 . . ?
C23 C28 C27 119.78(18) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H1SA C1SA H1SB 109.5 . . ?
H1SA C1SA H1SC 109.5 . . ?
H1SB C1SA H1SC 109.5 . . ?
C2SA C1SA H1SA 109.5 . . ?
C2SA C1SA H1SB 109.5 . . ?
C2SA C1SA H1SC 109.5 . . ?
N1SA C2SA C1SA 169.3(19) . . ?
H1SD C1SB H1SE 109.5 . . ?
H1SD C1SB H1SF 109.5 . . ?
H1SE C1SB H1SF 109.5 . . ?
C2SB C1SB H1SD 109.5 . . ?
C2SB C1SB H1SE 109.5 . . ?
C2SB C1SB H1SF 109.5 . . ?
N1SB C2SB C1SB 175.2(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O5 1.00(3) 1.78(2) 2.6965(16) 151(2) 2_675

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -176.63(14) . . . . ?
O1 C2 C3 C16 -7.8(3) . . . . ?
O2 C1 C2 O1 -2.4(2) . . . . ?
O2 C1 C2 C3 179.86(14) . . . . ?
O4 C6 C7 C4 -0.86(18) . . . . ?
O4 C6 C7 C8 175.99(13) . . . . ?
O4 C6 C10 C9 -177.75(14) . . . . ?
O4 C6 C10 C11 1.4(2) . . . . ?
O6 C16 C17 C18 -155.89(17) . . . . ?
O6 C16 C17 C22 20.3(2) . . . . ?
N1 C1 C2 O1 177.24(12) . . . . ?
N1 C1 C2 C3 -0.49(16) . . . . ?
N1 C4 C5 O3 55.8(2) . . . . ?
N1 C4 C5 O4 -120.34(13) . . . . ?
N1 C4 C7 C6 117.93(14) . . . . ?
N1 C4 C7 C8 -58.6(2) . . . . ?
N1 C23 C24 C25 -179.00(17) . . . . ?
N1 C23 C28 C27 178.20(17) . . . . ?
N2 C9 C10 C6 1.3(2) . . . . ?
N2 C9 C10 C11 -177.92(14) . . . . ?
N2 C9 C14 C13 177.65(17) . . . . ?
C1 N1 C4 C3 0.44(15) . . . . ?
C1 N1 C4 C5 -118.54(13) . . . . ?
C1 N1 C4 C7 129.64(13) . . . . ?
C1 N1 C23 C24 101.64(19) . . . . ?
C1 N1 C23 C28 -78.3(2) . . . . ?
C1 C2 C3 C4 0.75(16) . . . . ?
C1 C2 C3 C16 169.60(16) . . . . ?
C2 C3 C4 N1 -0.73(15) . . . . ?
C2 C3 C4 C5 117.49(13) . . . . ?
C2 C3 C4 C7 -127.79(14) . . . . ?
C2 C3 C16 O6 -151.39(18) . . . . ?
C2 C3 C16 C17 29.4(3) . . . . ?
C3 C4 C5 O3 -58.6(2) . . . . ?
C3 C4 C5 O4 125.25(14) . . . . ?
C3 C4 C7 C6 -120.16(14) . . . . ?
C3 C4 C7 C8 63.3(2) . . . . ?
C3 C16 C17 C18 23.3(2) . . . . ?
C3 C16 C17 C22 -160.45(16) . . . . ?
C4 N1 C1 O2 179.62(14) . . . . ?
C4 N1 C1 C2 -0.01(16) . . . . ?
C4 N1 C23 C24 -82.7(2) . . . . ?
C4 N1 C23 C28 97.34(19) . . . . ?
C4 C3 C16 O6 16.8(2) . . . . ?
C4 C3 C16 C17 -162.45(13) . . . . ?
C4 C7 C8 O5 -0.7(3) . . . . ?
C4 C7 C8 N2 178.42(14) . . . . ?
C5 O4 C6 C7 0.97(18) . . . . ?
C5 O4 C6 C10 179.50(14) . . . . ?
C5 C4 C7 C6 0.38(16) . . . . ?
C5 C4 C7 C8 -176.16(15) . . . . ?
C6 O4 C5 O3 -177.17(17) . . . . ?
C6 O4 C5 C4 -0.66(17) . . . . ?
C6 C7 C8 O5 -176.82(15) . . . . ?
C6 C7 C8 N2 2.3(2) . . . . ?
C6 C10 C11 C12 -178.74(17) . . . . ?
C7 C4 C5 O3 176.35(19) . . . . ?
C7 C4 C5 O4 0.18(16) . . . . ?
C7 C6 C10 C9 0.6(2) . . . . ?
C7 C6 C10 C11 179.83(15) . . . . ?
C8 N2 C9 C10 -1.4(2) . . . . ?
C8 N2 C9 C14 -179.51(15) . . . . ?
C9 N2 C8 O5 178.78(14) . . . . ?
C9 N2 C8 C7 -0.3(2) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C6 C7 C4 -179.36(14) . . . . ?
C10 C6 C7 C8 -2.5(2) . . . . ?
C10 C9 C14 C13 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C14 C9 C10 C6 179.42(15) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C15 N2 C8 O5 0.8(2) . . . . ?
C15 N2 C8 C7 -178.32(15) . . . . ?
C15 N2 C9 C10 176.49(16) . . . . ?
C15 N2 C9 C14 -1.6(2) . . . . ?
C16 C3 C4 N1 -172.08(12) . . . . ?
C16 C3 C4 C5 -53.86(17) . . . . ?
C16 C3 C4 C7 60.87(18) . . . . ?
C16 C17 C18 C19 175.34(18) . . . . ?
C16 C17 C22 C21 -178.3(2) . . . . ?
C17 C18 C19 C20 2.9(4) . . . . ?
C18 C17 C22 C21 -1.9(3) . . . . ?
C18 C19 C20 C21 -2.2(5) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C20 C21 C22 C17 2.6(4) . . . . ?
C22 C17 C18 C19 -0.9(3) . . . . ?
C23 N1 C1 O2 -4.3(2) . . . . ?
C23 N1 C1 C2 176.08(13) . . . . ?
C23 N1 C4 C3 -175.73(13) . . . . ?
C23 N1 C4 C5 65.30(17) . . . . ?
C23 N1 C4 C7 -46.52(19) . . . . ?
C23 C24 C25 C26 0.9(3) . . . . ?
C24 C23 C28 C27 -1.7(3) . . . . ?
C24 C25 C26 C27 -1.9(3) . . . . ?
C24 C25 C26 C29 176.8(2) . . . . ?
C25 C26 C27 C28 1.0(3) . . . . ?
C26 C27 C28 C23 0.7(3) . . . . ?
C28 C23 C24 C25 0.9(3) . . . . ?
C29 C26 C27 C28 -177.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method acetonitrile
