# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_is_is29d1
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;\
1-{2-[(2,4-Dimethylphenyl)amino]-5-[(2-hydroxyphenyl)carbonyl]furan-3-yl}\
ethan-1-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'A b a 2'
_symmetry_space_group_name_Hall  'A 2 -2ac'
_symmetry_Int_Tables_number      41

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

_cell_length_a                   53.5172(16)
_cell_length_b                   17.0124(6)
_cell_length_c                   7.5768(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6898.3(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5710
_cell_measurement_theta_min      4.850
_cell_measurement_theta_max      50.896

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2944
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9725
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17536
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_h_max       63
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         28.00
_reflns_number_total             5398
_reflns_number_gt                4479
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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)+(0.0426P)²+0.9736P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(9)
_refine_ls_number_reflns         5398
_refine_ls_number_parameters     491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.63130(5) 0.97026(13) 1.0019(3) 0.0261(6) Uani 1 1 d . . .
O1 O 0.59734(3) 0.88989(8) 0.9391(2) 0.0214(4) Uani 1 1 d . . .
O2 O 0.57162(4) 0.76267(9) 0.8528(3) 0.0350(5) Uani 1 1 d . . .
O3 O 0.54036(4) 0.69591(10) 0.6315(3) 0.0327(5) Uani 1 1 d . . .
O4 O 0.62143(4) 1.12041(10) 0.8829(2) 0.0400(5) Uani 1 1 d . . .
C1 C 0.60841(5) 0.96091(14) 0.9356(3) 0.0226(6) Uani 1 1 d . . .
C2 C 0.59334(5) 1.01643(13) 0.8559(3) 0.0220(6) Uani 1 1 d . . .
C3 C 0.57169(5) 0.97546(13) 0.8030(3) 0.0246(6) Uani 1 1 d . . .
H3 H 0.5578 0.9974 0.7423 0.030 Uiso 1 1 calc R . .
C5 C 0.60061(6) 1.09837(14) 0.8323(3) 0.0301(7) Uani 1 1 d . . .
C6 C 0.58235(6) 1.15399(14) 0.7509(4) 0.0426(8) Uani 1 1 d . . .
H6A H 0.5697 1.1687 0.8385 0.064 Uiso 1 1 calc R . .
H6B H 0.5742 1.1286 0.6502 0.064 Uiso 1 1 calc R . .
H6C H 0.5912 1.2012 0.7107 0.064 Uiso 1 1 calc R . .
C7 C 0.56072(5) 0.82637(14) 0.8244(3) 0.0243(6) Uani 1 1 d . . .
C8 C 0.53533(5) 0.82746(13) 0.7497(3) 0.0215(6) Uani 1 1 d . . .
C9 C 0.52671(5) 0.76204(13) 0.6539(3) 0.0244(6) Uani 1 1 d . . .
C10 C 0.50362(5) 0.76408(15) 0.5727(3) 0.0283(7) Uani 1 1 d . . .
H10 H 0.4983 0.7206 0.5038 0.034 Uiso 1 1 calc R . .
C11 C 0.48824(5) 0.82851(15) 0.5904(4) 0.0344(7) Uani 1 1 d . . .
H11 H 0.4724 0.8294 0.5335 0.041 Uiso 1 1 calc R . .
C12 C 0.49583(5) 0.89174(15) 0.6911(4) 0.0352(7) Uani 1 1 d . . .
H12 H 0.4851 0.9357 0.7060 0.042 Uiso 1 1 calc R . .
C13 C 0.51904(5) 0.89111(14) 0.7699(3) 0.0274(7) Uani 1 1 d . . .
H13 H 0.5241 0.9348 0.8394 0.033 Uiso 1 1 calc R . .
C14 C 0.64788(5) 0.91679(15) 1.0837(3) 0.0253(7) Uani 1 1 d . . .
C15 C 0.67216(5) 0.94304(15) 1.1145(3) 0.0265(6) Uani 1 1 d . . .
C16 C 0.68869(5) 0.89181(16) 1.1964(3) 0.0315(7) Uani 1 1 d . . .
H16 H 0.7053 0.9091 1.2179 0.038 Uiso 1 1 calc R . .
C17 C 0.68190(6) 0.81562(15) 1.2485(3) 0.0305(7) Uani 1 1 d . . .
C18 C 0.65764(6) 0.79236(16) 1.2153(3) 0.0293(7) Uani 1 1 d . . .
H18 H 0.6525 0.7411 1.2493 0.035 Uiso 1 1 calc R . .
C19 C 0.64073(5) 0.84141(14) 1.1343(3) 0.0269(6) Uani 1 1 d . . .
H19 H 0.6242 0.8238 1.1128 0.032 Uiso 1 1 calc R . .
C20 C 0.68039(5) 1.02477(15) 1.0648(4) 0.0364(7) Uani 1 1 d . . .
H20A H 0.6708 1.0634 1.1327 0.055 Uiso 1 1 calc R . .
H20B H 0.6775 1.0332 0.9384 0.055 Uiso 1 1 calc R . .
H20C H 0.6982 1.0309 1.0909 0.055 Uiso 1 1 calc R . .
C21 C 0.70036(6) 0.76189(15) 1.3371(4) 0.0441(8) Uani 1 1 d . . .
H21A H 0.6926 0.7382 1.4416 0.066 Uiso 1 1 calc R . .
H21B H 0.7151 0.7921 1.3725 0.066 Uiso 1 1 calc R . .
H21C H 0.7053 0.7203 1.2547 0.066 Uiso 1 1 calc R . .
H1 H 0.6355(5) 1.0224(15) 0.994(4) 0.039(8) Uiso 1 1 d . . .
H3A H 0.5535(6) 0.6983(17) 0.705(4) 0.053(10) Uiso 1 1 d . . .
N2 N 0.68404(4) 0.89974(12) 0.6621(3) 0.0243(5) Uani 1 1 d . . .
O5 O 0.64689(3) 0.94365(9) 0.53399(19) 0.0222(4) Uani 1 1 d . . .
O6 O 0.61388(4) 1.03729(10) 0.4048(2) 0.0393(5) Uani 1 1 d . . .
O7 O 0.57095(5) 1.08316(10) 0.3209(3) 0.0610(7) Uani 1 1 d . . .
O8 O 0.67694(4) 0.75190(9) 0.7956(2) 0.0341(5) Uani 1 1 d . . .
C4 C 0.57411(5) 0.89912(13) 0.8539(3) 0.0207(6) Uani 1 1 d . . .
C22 C 0.66000(5) 0.88928(14) 0.6210(3) 0.0224(6) Uani 1 1 d . . .
C23 C 0.64520(5) 0.82398(14) 0.6615(3) 0.0221(6) Uani 1 1 d . . .
C24 C 0.62156(5) 0.84182(13) 0.5913(3) 0.0222(6) Uani 1 1 d . . .
H24 H 0.6072 0.8091 0.5981 0.027 Uiso 1 1 calc R . .
C25 C 0.62254(5) 0.91339(13) 0.5122(3) 0.0211(6) Uani 1 1 d . . .
C26 C 0.65468(6) 0.75604(14) 0.7567(3) 0.0258(7) Uani 1 1 d . . .
C27 C 0.63660(5) 0.69224(13) 0.8032(4) 0.0322(7) Uani 1 1 d . . .
H27A H 0.6307 0.6666 0.6951 0.048 Uiso 1 1 calc R . .
H27B H 0.6223 0.7149 0.8662 0.048 Uiso 1 1 calc R . .
H27C H 0.6449 0.6535 0.8789 0.048 Uiso 1 1 calc R . .
C29 C 0.60614(5) 0.96846(14) 0.4245(3) 0.0257(6) Uani 1 1 d . . .
C30 C 0.58111(5) 0.94625(14) 0.3620(3) 0.0236(6) Uani 1 1 d . . .
C31 C 0.56425(6) 1.00587(13) 0.3166(4) 0.0342(7) Uani 1 1 d . . .
C32 C 0.54002(6) 0.98825(16) 0.2672(4) 0.0458(9) Uani 1 1 d . . .
H32 H 0.5286 1.0294 0.2418 0.055 Uiso 1 1 calc R . .
C33 C 0.53252(6) 0.91151(16) 0.2549(3) 0.0358(7) Uani 1 1 d . . .
H33 H 0.5158 0.8996 0.2224 0.043 Uiso 1 1 calc R . .
C34 C 0.54918(5) 0.85093(15) 0.2895(3) 0.0304(7) Uani 1 1 d . . .
H34 H 0.5441 0.7977 0.2766 0.036 Uiso 1 1 calc R . .
C35 C 0.57298(5) 0.86876(14) 0.3426(3) 0.0267(6) Uani 1 1 d . . .
H35 H 0.5843 0.8271 0.3670 0.032 Uiso 1 1 calc R . .
C36 C 0.70026(5) 0.96437(14) 0.6331(3) 0.0228(6) Uani 1 1 d . . .
C37 C 0.72445(5) 0.95718(15) 0.7010(3) 0.0255(6) Uani 1 1 d . . .
C38 C 0.74073(5) 1.02014(14) 0.6749(3) 0.0300(7) Uani 1 1 d . . .
H38 H 0.7573 1.0161 0.7191 0.036 Uiso 1 1 calc R . .
C39 C 0.73384(5) 1.08843(14) 0.5874(3) 0.0280(7) Uani 1 1 d . . .
C40 C 0.70971(6) 1.09343(14) 0.5229(3) 0.0298(7) Uani 1 1 d . . .
H40 H 0.7046 1.1395 0.4620 0.036 Uiso 1 1 calc R . .
C41 C 0.69280(5) 1.03248(14) 0.5453(3) 0.0279(7) Uani 1 1 d . . .
H41 H 0.6762 1.0371 0.5013 0.034 Uiso 1 1 calc R . .
C42 C 0.73289(5) 0.88507(14) 0.7983(4) 0.0367(7) Uani 1 1 d . . .
H42A H 0.7495 0.8942 0.8483 0.055 Uiso 1 1 calc R . .
H42B H 0.7336 0.8405 0.7165 0.055 Uiso 1 1 calc R . .
H42C H 0.7211 0.8734 0.8936 0.055 Uiso 1 1 calc R . .
C43 C 0.75253(6) 1.15422(14) 0.5610(4) 0.0394(7) Uani 1 1 d . . .
H43A H 0.7647 1.1387 0.4712 0.059 Uiso 1 1 calc R . .
H43B H 0.7612 1.1648 0.6726 0.059 Uiso 1 1 calc R . .
H43C H 0.7438 1.2018 0.5223 0.059 Uiso 1 1 calc R . .
H2 H 0.6900(5) 0.8548(16) 0.731(4) 0.056(9) Uiso 1 1 d . . .
H7 H 0.5904(7) 1.084(2) 0.344(5) 0.101(14) Uiso 1 1 d . . .


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

# MOLECULAR GEOMETRY

_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
N1 C1 1.334(3) . ?
N1 C14 1.414(3) . ?
N1 H1 0.92(3) . ?
O1 C1 1.346(3) . ?
O1 C4 1.410(3) . ?
O2 C7 1.249(3) . ?
O3 C9 1.352(3) . ?
O3 H3A 0.90(3) . ?
O4 C5 1.236(3) . ?
C1 C2 1.381(3) . ?
C2 C3 1.410(3) . ?
C2 C5 1.458(3) . ?
C3 C4 1.361(3) . ?
C3 H3 0.9500 . ?
C5 C6 1.494(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C4 1.448(3) . ?
C7 C8 1.472(3) . ?
C8 C13 1.399(3) . ?
C8 C9 1.406(3) . ?
C9 C10 1.381(4) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.392(3) . ?
C14 C15 1.393(4) . ?
C15 C16 1.388(4) . ?
C15 C20 1.506(4) . ?
C16 C17 1.403(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(4) . ?
C17 C21 1.504(4) . ?
C18 C19 1.376(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N2 C22 1.336(3) . ?
N2 C36 1.418(3) . ?
N2 H2 0.98(3) . ?
O5 C22 1.335(3) . ?
O5 C25 1.411(3) . ?
O6 C29 1.251(3) . ?
O7 C31 1.363(3) . ?
O7 H7 1.05(4) . ?
O8 C26 1.229(3) . ?
C22 C23 1.399(3) . ?
C23 C24 1.406(3) . ?
C23 C26 1.454(3) . ?
C24 C25 1.358(3) . ?
C24 H24 0.9500 . ?
C25 C29 1.446(3) . ?
C26 C27 1.496(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C29 C30 1.470(4) . ?
C30 C35 1.396(3) . ?
C30 C31 1.400(3) . ?
C31 C32 1.382(4) . ?
C32 C33 1.369(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.369(4) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 C41 1.394(3) . ?
C36 C37 1.398(4) . ?
C37 C38 1.395(3) . ?
C37 C42 1.501(3) . ?
C38 C39 1.388(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.383(4) . ?
C39 C43 1.514(3) . ?
C40 C41 1.387(3) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?

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
C1 N1 C14 131.7(2) . . ?
C1 N1 H1 108.3(17) . . ?
C14 N1 H1 119.9(17) . . ?
C1 O1 C4 106.22(17) . . ?
C9 O3 H3A 108.0(19) . . ?
N1 C1 O1 120.3(2) . . ?
N1 C1 C2 128.3(2) . . ?
O1 C1 C2 111.4(2) . . ?
C1 C2 C3 105.4(2) . . ?
C1 C2 C5 123.5(2) . . ?
C3 C2 C5 131.1(2) . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
O4 C5 C2 119.5(2) . . ?
O4 C5 C6 121.7(2) . . ?
C2 C5 C6 118.8(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 C4 118.9(2) . . ?
O2 C7 C8 120.5(2) . . ?
C4 C7 C8 120.4(2) . . ?
C13 C8 C9 117.7(2) . . ?
C13 C8 C7 122.9(2) . . ?
C9 C8 C7 119.4(2) . . ?
O3 C9 C10 116.7(2) . . ?
O3 C9 C8 123.1(2) . . ?
C10 C9 C8 120.2(2) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 121.4(2) . . ?
C12 C13 H13 119.3 . . ?
C8 C13 H13 119.3 . . ?
C19 C14 C15 120.4(2) . . ?
C19 C14 N1 122.7(3) . . ?
C15 C14 N1 116.9(2) . . ?
C16 C15 C14 117.9(2) . . ?
C16 C15 C20 120.3(3) . . ?
C14 C15 C20 121.8(2) . . ?
C15 C16 C17 122.8(3) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C16 117.2(2) . . ?
C18 C17 C21 121.7(3) . . ?
C16 C17 C21 121.2(3) . . ?
C19 C18 C17 121.7(3) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 N2 C36 131.1(2) . . ?
C22 N2 H2 109.5(16) . . ?
C36 N2 H2 119.2(17) . . ?
C22 O5 C25 106.88(18) . . ?
C31 O7 H7 106.2(19) . . ?
C3 C4 O1 108.7(2) . . ?
C3 C4 C7 136.5(2) . . ?
O1 C4 C7 114.33(19) . . ?
O5 C22 N2 121.9(2) . . ?
O5 C22 C23 111.2(2) . . ?
N2 C22 C23 126.9(2) . . ?
C22 C23 C24 104.8(2) . . ?
C22 C23 C26 122.9(3) . . ?
C24 C23 C26 132.3(2) . . ?
C25 C24 C23 109.0(2) . . ?
C25 C24 H24 125.5 . . ?
C23 C24 H24 125.5 . . ?
C24 C25 O5 108.1(2) . . ?
C24 C25 C29 139.5(3) . . ?
O5 C25 C29 112.2(2) . . ?
O8 C26 C23 120.2(2) . . ?
O8 C26 C27 121.9(2) . . ?
C23 C26 C27 117.9(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C29 C25 117.4(2) . . ?
O6 C29 C30 120.3(2) . . ?
C25 C29 C30 122.3(2) . . ?
C35 C30 C31 117.2(2) . . ?
C35 C30 C29 124.1(2) . . ?
C31 C30 C29 118.7(2) . . ?
O7 C31 C32 117.5(2) . . ?
O7 C31 C30 121.5(3) . . ?
C32 C31 C30 120.9(2) . . ?
C33 C32 C31 120.0(3) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.5(3) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 119.2(2) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C30 122.0(2) . . ?
C34 C35 H35 119.0 . . ?
C30 C35 H35 119.0 . . ?
C41 C36 C37 120.9(2) . . ?
C41 C36 N2 122.9(2) . . ?
C37 C36 N2 116.2(2) . . ?
C38 C37 C36 117.3(2) . . ?
C38 C37 C42 120.6(2) . . ?
C36 C37 C42 122.1(2) . . ?
C39 C38 C37 123.0(3) . . ?
C39 C38 H38 118.5 . . ?
C37 C38 H38 118.5 . . ?
C40 C39 C38 117.9(2) . . ?
C40 C39 C43 121.6(2) . . ?
C38 C39 C43 120.4(3) . . ?
C39 C40 C41 121.3(2) . . ?
C39 C40 H40 119.3 . . ?
C41 C40 H40 119.3 . . ?
C40 C41 C36 119.5(3) . . ?
C40 C41 H41 120.2 . . ?
C36 C41 H41 120.2 . . ?
C37 C42 H42A 109.5 . . ?
C37 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C37 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C39 C43 H43A 109.5 . . ?
C39 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C39 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?

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
C14 N1 C1 O1 -0.5(4) . . . . ?
C14 N1 C1 C2 -179.5(2) . . . . ?
C4 O1 C1 N1 -177.8(2) . . . . ?
C4 O1 C1 C2 1.3(3) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
O1 C1 C2 C3 -1.5(3) . . . . ?
N1 C1 C2 C5 -0.5(4) . . . . ?
O1 C1 C2 C5 -179.5(2) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C5 C2 C3 C4 178.8(2) . . . . ?
C1 C2 C5 O4 1.1(4) . . . . ?
C3 C2 C5 O4 -176.2(3) . . . . ?
C1 C2 C5 C6 -177.5(2) . . . . ?
C3 C2 C5 C6 5.1(4) . . . . ?
O2 C7 C8 C13 157.4(2) . . . . ?
C4 C7 C8 C13 -27.1(4) . . . . ?
O2 C7 C8 C9 -22.4(4) . . . . ?
C4 C7 C8 C9 153.1(2) . . . . ?
C13 C8 C9 O3 -177.3(2) . . . . ?
C7 C8 C9 O3 2.5(4) . . . . ?
C13 C8 C9 C10 4.7(4) . . . . ?
C7 C8 C9 C10 -175.6(2) . . . . ?
O3 C9 C10 C11 179.0(2) . . . . ?
C8 C9 C10 C11 -2.9(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C9 C8 C13 C12 -3.4(4) . . . . ?
C7 C8 C13 C12 176.8(2) . . . . ?
C1 N1 C14 C19 -10.2(4) . . . . ?
C1 N1 C14 C15 170.5(2) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
N1 C14 C15 C16 179.3(2) . . . . ?
C19 C14 C15 C20 -178.8(2) . . . . ?
N1 C14 C15 C20 0.5(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C20 C15 C16 C17 178.8(2) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C15 C16 C17 C21 -179.9(2) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C21 C17 C18 C19 -180.0(2) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C15 C14 C19 C18 0.1(4) . . . . ?
N1 C14 C19 C18 -179.2(2) . . . . ?
C2 C3 C4 O1 -0.3(3) . . . . ?
C2 C3 C4 C7 -171.1(3) . . . . ?
C1 O1 C4 C3 -0.6(2) . . . . ?
C1 O1 C4 C7 172.48(19) . . . . ?
O2 C7 C4 C3 161.1(3) . . . . ?
C8 C7 C4 C3 -14.5(4) . . . . ?
O2 C7 C4 O1 -9.4(3) . . . . ?
C8 C7 C4 O1 175.1(2) . . . . ?
C25 O5 C22 N2 179.6(2) . . . . ?
C25 O5 C22 C23 -1.1(2) . . . . ?
C36 N2 C22 O5 1.8(4) . . . . ?
C36 N2 C22 C23 -177.4(2) . . . . ?
O5 C22 C23 C24 0.3(3) . . . . ?
N2 C22 C23 C24 179.6(2) . . . . ?
O5 C22 C23 C26 -179.7(2) . . . . ?
N2 C22 C23 C26 -0.5(4) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C26 C23 C24 C25 -179.3(2) . . . . ?
C23 C24 C25 O5 -1.3(3) . . . . ?
C23 C24 C25 C29 -176.2(3) . . . . ?
C22 O5 C25 C24 1.5(2) . . . . ?
C22 O5 C25 C29 177.9(2) . . . . ?
C22 C23 C26 O8 -4.7(3) . . . . ?
C24 C23 C26 O8 175.3(2) . . . . ?
C22 C23 C26 C27 175.8(2) . . . . ?
C24 C23 C26 C27 -4.2(4) . . . . ?
C24 C25 C29 O6 164.1(3) . . . . ?
O5 C25 C29 O6 -10.7(3) . . . . ?
C24 C25 C29 C30 -15.0(5) . . . . ?
O5 C25 C29 C30 170.2(2) . . . . ?
O6 C29 C30 C35 165.4(2) . . . . ?
C25 C29 C30 C35 -15.5(4) . . . . ?
O6 C29 C30 C31 -13.9(4) . . . . ?
C25 C29 C30 C31 165.2(2) . . . . ?
C35 C30 C31 O7 -176.0(3) . . . . ?
C29 C30 C31 O7 3.3(4) . . . . ?
C35 C30 C31 C32 4.6(4) . . . . ?
C29 C30 C31 C32 -176.1(3) . . . . ?
O7 C31 C32 C33 177.8(3) . . . . ?
C30 C31 C32 C33 -2.8(4) . . . . ?
C31 C32 C33 C34 -0.8(4) . . . . ?
C32 C33 C34 C35 2.4(4) . . . . ?
C33 C34 C35 C30 -0.4(4) . . . . ?
C31 C30 C35 C34 -3.0(4) . . . . ?
C29 C30 C35 C34 177.7(2) . . . . ?
C22 N2 C36 C41 -1.5(4) . . . . ?
C22 N2 C36 C37 177.2(2) . . . . ?
C41 C36 C37 C38 -1.0(3) . . . . ?
N2 C36 C37 C38 -179.7(2) . . . . ?
C41 C36 C37 C42 179.1(2) . . . . ?
N2 C36 C37 C42 0.4(3) . . . . ?
C36 C37 C38 C39 0.6(4) . . . . ?
C42 C37 C38 C39 -179.4(2) . . . . ?
C37 C38 C39 C40 -0.3(4) . . . . ?
C37 C38 C39 C43 -179.1(2) . . . . ?
C38 C39 C40 C41 0.3(4) . . . . ?
C43 C39 C40 C41 179.1(2) . . . . ?
C39 C40 C41 C36 -0.7(4) . . . . ?
C37 C36 C41 C40 1.0(4) . . . . ?
N2 C36 C41 C40 179.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.800
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.800
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 982675'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_is_is3801
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;\
N-(4-Chlorophenyl)-5-[(2-hydroxy-4-methoxyphenyl)carbonyl]-2-\
methylfuran-3-carboxamide * dimethylsulfoxide
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Cl N O5, C2 H6 O S'
_chemical_formula_sum            'C22 H22 Cl N O6 S'
_chemical_formula_weight         463.92

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'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_Int_Tables_number      11

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

_cell_length_a                   9.7020(2)
_cell_length_b                   6.89430(10)
_cell_length_c                   16.0179(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2010(10)
_cell_angle_gamma                90.00
_cell_volume                     1071.18(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8112
_cell_measurement_theta_min      4.864
_cell_measurement_theta_max      70.723

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18612
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         31.99
_reflns_number_total             3979
_reflns_number_gt                3373
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex v7.51a'
_computing_cell_refinement       'Bruker Apex v7.51a'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms (except H1/H3) were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). 
 
 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)+(0.0640P)²+0.2644P] 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         3979
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1038
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34906(6) 0.2500 0.61587(3) 0.05817(18) Uani 1 2 d S . .
N1 N 0.16332(12) 0.2500 0.26115(7) 0.0230(2) Uani 1 2 d S . .
O1 O 0.13437(10) 0.2500 -0.02760(6) 0.0229(2) Uani 1 2 d S . .
O2 O -0.23026(11) 0.2500 -0.00290(7) 0.0312(2) Uani 1 2 d S . .
O3 O -0.37322(11) 0.2500 -0.13611(8) 0.0366(3) Uani 1 2 d S . .
O4 O -0.13766(13) 0.2500 -0.39372(7) 0.0373(3) Uani 1 2 d S . .
O5 O 0.36757(11) 0.2500 0.19345(7) 0.0335(3) Uani 1 2 d S . .
C1 C 0.00603(13) 0.2500 0.00771(8) 0.0200(2) Uani 1 2 d S . .
C2 C 0.02103(14) 0.2500 0.09236(8) 0.0212(2) Uani 1 2 d S . .
H2 H -0.0509 0.2500 0.1317 0.025 Uiso 1 2 calc SR . .
C3 C 0.16536(13) 0.2500 0.11073(8) 0.0197(2) Uani 1 2 d S . .
C4 C 0.22964(13) 0.2500 0.03542(9) 0.0215(2) Uani 1 2 d S . .
C5 C -0.12107(14) 0.2500 -0.04346(9) 0.0213(2) Uani 1 2 d S . .
C6 C -0.12504(13) 0.2500 -0.13425(8) 0.0204(2) Uani 1 2 d S . .
C7 C -0.25415(14) 0.2500 -0.17724(9) 0.0228(3) Uani 1 2 d S . .
C8 C -0.26279(15) 0.2500 -0.26430(9) 0.0260(3) Uani 1 2 d S . .
H8 H -0.3502 0.2500 -0.2922 0.031 Uiso 1 2 calc SR . .
C9 C -0.14302(16) 0.2500 -0.30957(9) 0.0269(3) Uani 1 2 d S . .
C10 C -0.01439(17) 0.2500 -0.26879(10) 0.0377(4) Uani 1 2 d S . .
H10 H 0.0674 0.2500 -0.3004 0.045 Uiso 1 2 calc SR . .
C11 C -0.00613(16) 0.2500 -0.18363(10) 0.0327(3) Uani 1 2 d S . .
H11 H 0.0821 0.2500 -0.1568 0.039 Uiso 1 2 calc SR . .
C12 C -0.2643(2) 0.2500 -0.44075(11) 0.0389(4) Uani 1 2 d S . .
H12A H -0.3181 0.1348 -0.4265 0.058 Uiso 0.50 1 calc PR . .
H12B H -0.2447 0.2483 -0.5005 0.058 Uiso 1 2 calc SR . .
H12C H -0.3170 0.3669 -0.4276 0.058 Uiso 0.50 1 calc PR . .
C13 C 0.24097(14) 0.2500 0.19170(8) 0.0213(2) Uani 1 2 d S . .
C14 C 0.21303(14) 0.2500 0.34444(9) 0.0235(3) Uani 1 2 d S . .
C15 C 0.11608(16) 0.2500 0.40715(10) 0.0332(3) Uani 1 2 d S . .
H15 H 0.0207 0.2500 0.3925 0.040 Uiso 1 2 calc SR . .
C16 C 0.15646(18) 0.2500 0.49065(10) 0.0389(4) Uani 1 2 d S . .
H16 H 0.0895 0.2500 0.5331 0.047 Uiso 1 2 calc SR . .
C17 C 0.29539(18) 0.2500 0.51137(10) 0.0338(3) Uani 1 2 d S . .
C18 C 0.39306(17) 0.2500 0.45050(10) 0.0342(3) Uani 1 2 d S . .
H18 H 0.4882 0.2500 0.4657 0.041 Uiso 1 2 calc SR . .
C19 C 0.35291(16) 0.2500 0.36679(10) 0.0315(3) Uani 1 2 d S . .
H19 H 0.4206 0.2500 0.3248 0.038 Uiso 1 2 calc SR . .
C20 C 0.37586(16) 0.2500 0.00991(10) 0.0329(3) Uani 1 2 d S . .
H20A H 0.4114 0.1169 0.0109 0.049 Uiso 0.50 1 calc PR . .
H20B H 0.4305 0.3304 0.0487 0.049 Uiso 0.50 1 calc PR . .
H20C H 0.3822 0.3026 -0.0467 0.049 Uiso 0.50 1 calc PR . .
H1 H 0.075(2) 0.2500 0.2557(14) 0.036(5) Uiso 1 2 d S . .
H3 H -0.347(3) 0.2500 -0.0819(18) 0.059(8) Uiso 1 2 d S . .
S1 S 0.70997(4) 0.2500 0.26128(2) 0.02772(10) Uani 1 2 d S . .
O6 O 0.86407(12) 0.2500 0.27088(8) 0.0405(3) Uani 1 2 d S . .
C21 C 0.66761(12) 0.05519(17) 0.19187(8) 0.0335(2) Uani 1 1 d . . .
H21A H 0.7134 0.0752 0.1386 0.050 Uiso 1 1 calc R . .
H21B H 0.5676 0.0511 0.1823 0.050 Uiso 1 1 calc R . .
H21C H 0.6986 -0.0677 0.2166 0.050 Uiso 1 1 calc R . .


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

# MOLECULAR GEOMETRY

_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
Cl1 C17 1.7426(17) . ?
N1 C13 1.3566(17) . ?
N1 C14 1.4090(18) . ?
N1 H1 0.86(2) . ?
O1 C4 1.3544(16) . ?
O1 C1 1.3784(16) . ?
O2 C5 1.2543(17) . ?
O3 C7 1.3418(18) . ?
O3 H3 0.90(3) . ?
O4 C9 1.3500(18) . ?
O4 C12 1.427(2) . ?
O5 C13 1.2280(17) . ?
C1 C2 1.3607(19) . ?
C1 C5 1.4664(19) . ?
C2 C3 1.4248(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3695(18) . ?
C3 C13 1.4767(19) . ?
C4 C20 1.4844(19) . ?
C5 C6 1.4539(19) . ?
C6 C11 1.412(2) . ?
C6 C7 1.4167(19) . ?
C7 C8 1.395(2) . ?
C8 C9 1.382(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(2) . ?
C10 C11 1.365(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.390(2) . ?
C14 C19 1.396(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S1 O6 1.4998(12) . ?
S1 C21 1.7861(12) . ?
S1 C21 1.7861(12) 4_565 ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C13 N1 C14 126.26(12) . . ?
C13 N1 H1 119.1(15) . . ?
C14 N1 H1 114.7(15) . . ?
C4 O1 C1 107.60(10) . . ?
C7 O3 H3 104.5(18) . . ?
C9 O4 C12 118.44(14) . . ?
C2 C1 O1 109.29(11) . . ?
C2 C1 C5 128.92(12) . . ?
O1 C1 C5 121.80(12) . . ?
C1 C2 C3 106.85(11) . . ?
C1 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
C4 C3 C2 106.37(12) . . ?
C4 C3 C13 123.13(12) . . ?
C2 C3 C13 130.49(12) . . ?
O1 C4 C3 109.89(11) . . ?
O1 C4 C20 115.85(12) . . ?
C3 C4 C20 134.26(13) . . ?
O2 C5 C6 120.88(12) . . ?
O2 C5 C1 114.83(12) . . ?
C6 C5 C1 124.29(12) . . ?
C11 C6 C7 116.88(13) . . ?
C11 C6 C5 123.73(12) . . ?
C7 C6 C5 119.39(12) . . ?
O3 C7 C8 117.15(13) . . ?
O3 C7 C6 121.53(13) . . ?
C8 C7 C6 121.31(13) . . ?
C9 C8 C7 119.38(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
O4 C9 C8 125.04(14) . . ?
O4 C9 C10 114.47(14) . . ?
C8 C9 C10 120.49(14) . . ?
C11 C10 C9 120.05(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 121.88(14) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 N1 123.62(13) . . ?
O5 C13 C3 119.89(12) . . ?
N1 C13 C3 116.49(12) . . ?
C15 C14 C19 118.90(13) . . ?
C15 C14 N1 117.43(13) . . ?
C19 C14 N1 123.67(13) . . ?
C16 C15 C14 121.03(14) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.11(15) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 120.91(15) . . ?
C18 C17 Cl1 119.02(13) . . ?
C16 C17 Cl1 120.08(13) . . ?
C17 C18 C19 120.11(15) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 119.95(14) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 S1 C21 106.24(5) . . ?
O6 S1 C21 106.24(5) . 4_565 ?
C21 S1 C21 97.53(8) . 4_565 ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C4 O1 C1 C2 0.0 . . . . ?
C4 O1 C1 C5 180.0 . . . . ?
O1 C1 C2 C3 0.0 . . . . ?
C5 C1 C2 C3 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C13 180.0 . . . . ?
C1 O1 C4 C3 0.0 . . . . ?
C1 O1 C4 C20 180.0 . . . . ?
C2 C3 C4 O1 0.0 . . . . ?
C13 C3 C4 O1 180.0 . . . . ?
C2 C3 C4 C20 180.0 . . . . ?
C13 C3 C4 C20 0.0 . . . . ?
C2 C1 C5 O2 0.0 . . . . ?
O1 C1 C5 O2 180.0 . . . . ?
C2 C1 C5 C6 180.0 . . . . ?
O1 C1 C5 C6 0.0 . . . . ?
O2 C5 C6 C11 180.0 . . . . ?
C1 C5 C6 C11 0.0 . . . . ?
O2 C5 C6 C7 0.0 . . . . ?
C1 C5 C6 C7 180.0 . . . . ?
C11 C6 C7 O3 180.0 . . . . ?
C5 C6 C7 O3 0.0 . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
C5 C6 C7 C8 180.0 . . . . ?
O3 C7 C8 C9 180.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C12 O4 C9 C8 0.0 . . . . ?
C12 O4 C9 C10 180.0 . . . . ?
C7 C8 C9 O4 180.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
O4 C9 C10 C11 180.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C6 0.0 . . . . ?
C7 C6 C11 C10 0.0 . . . . ?
C5 C6 C11 C10 180.0 . . . . ?
C14 N1 C13 O5 0.0 . . . . ?
C14 N1 C13 C3 180.0 . . . . ?
C4 C3 C13 O5 0.0 . . . . ?
C2 C3 C13 O5 180.0 . . . . ?
C4 C3 C13 N1 180.0 . . . . ?
C2 C3 C13 N1 0.0 . . . . ?
C13 N1 C14 C15 180.0 . . . . ?
C13 N1 C14 C19 0.0 . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
N1 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C15 C16 C17 Cl1 180.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
Cl1 C17 C18 C19 180.0 . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
N1 C14 C19 C18 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        31.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 982676'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_is_is411
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
3-Benzoyl-2-(phenylamino)-9H-furo[3,2-b]chromen-9-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 N O4'
_chemical_formula_sum            'C24 H15 N O4'
_chemical_formula_weight         381.37

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19

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

_cell_length_a                   4.9114(4)
_cell_length_b                   9.9314(7)
_cell_length_c                   36.687(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1789.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1919
_cell_measurement_theta_min      4.664
_cell_measurement_theta_max      44.045

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.99
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9099
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18306
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0811
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         28.50
_reflns_number_total             4548
_reflns_number_gt                2928
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refined.
 
 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)+(0.0428P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0141(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_number_reflns         4548
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.2999(4) 0.39824(19) 0.82206(5) 0.0297(5) Uani 1 1 d . . .
O1 O -0.1979(3) 0.50684(14) 0.87649(4) 0.0300(4) Uani 1 1 d . . .
O2 O 0.3358(3) 0.32929(14) 0.92025(4) 0.0280(4) Uani 1 1 d . . .
O3 O -0.1151(4) 0.67711(15) 0.94116(4) 0.0374(4) Uani 1 1 d . . .
O4 O 0.0470(3) 0.19210(15) 0.81065(4) 0.0344(4) Uani 1 1 d . . .
C1 C -0.1558(5) 0.4045(2) 0.85283(6) 0.0268(5) Uani 1 1 d . . .
C2 C 0.0466(4) 0.3144(2) 0.86481(6) 0.0256(5) Uani 1 1 d . . .
C3 C 0.1340(4) 0.3740(2) 0.89810(6) 0.0249(5) Uani 1 1 d . . .
C4 C -0.0097(5) 0.4871(2) 0.90484(6) 0.0269(5) Uani 1 1 d . . .
C5 C 0.0167(5) 0.5738(2) 0.93520(6) 0.0285(5) Uani 1 1 d . . .
C6 C 0.2333(5) 0.5220(2) 0.95986(6) 0.0269(5) Uani 1 1 d . . .
C7 C 0.3803(5) 0.4054(2) 0.95175(6) 0.0256(5) Uani 1 1 d . . .
C8 C 0.5823(5) 0.3563(2) 0.97470(6) 0.0292(5) Uani 1 1 d . . .
H8 H 0.6823 0.2776 0.9685 0.035 Uiso 1 1 calc R . .
C9 C 0.6337(5) 0.4246(2) 1.00664(6) 0.0318(6) Uani 1 1 d . . .
H9 H 0.7702 0.3921 1.0227 0.038 Uiso 1 1 calc R . .
C10 C 0.4890(5) 0.5403(2) 1.01572(6) 0.0334(6) Uani 1 1 d . . .
H10 H 0.5265 0.5861 1.0379 0.040 Uiso 1 1 calc R . .
C11 C 0.2927(5) 0.5881(2) 0.99260(6) 0.0303(5) Uani 1 1 d . . .
H11 H 0.1952 0.6674 0.9989 0.036 Uiso 1 1 calc R . .
C12 C 0.1306(5) 0.2017(2) 0.84267(6) 0.0266(5) Uani 1 1 d . . .
C13 C 0.3150(5) 0.0955(2) 0.85686(6) 0.0259(5) Uani 1 1 d . . .
C14 C 0.4926(5) 0.0355(2) 0.83257(6) 0.0361(6) Uani 1 1 d . . .
H14 H 0.4980 0.0644 0.8079 0.043 Uiso 1 1 calc R . .
C15 C 0.6619(5) -0.0665(2) 0.84422(7) 0.0441(7) Uani 1 1 d . . .
H15 H 0.7876 -0.1054 0.8276 0.053 Uiso 1 1 calc R . .
C16 C 0.6519(5) -0.1129(2) 0.87965(7) 0.0421(6) Uani 1 1 d . . .
H16 H 0.7688 -0.1836 0.8873 0.051 Uiso 1 1 calc R . .
C17 C 0.4716(5) -0.0560(2) 0.90369(7) 0.0383(6) Uani 1 1 d . . .
H17 H 0.4616 -0.0884 0.9280 0.046 Uiso 1 1 calc R . .
C18 C 0.3035(5) 0.0489(2) 0.89260(6) 0.0338(6) Uani 1 1 d . . .
H18 H 0.1806 0.0888 0.9094 0.041 Uiso 1 1 calc R . .
C19 C -0.5013(5) 0.4847(2) 0.80773(6) 0.0284(5) Uani 1 1 d . . .
C20 C -0.5912(5) 0.6005(2) 0.82498(7) 0.0405(6) Uani 1 1 d . . .
H20 H -0.5180 0.6259 0.8479 0.049 Uiso 1 1 calc R . .
C21 C -0.7885(6) 0.6786(3) 0.80844(7) 0.0493(7) Uani 1 1 d . . .
H21 H -0.8491 0.7584 0.8202 0.059 Uiso 1 1 calc R . .
C22 C -0.8994(5) 0.6436(3) 0.77532(7) 0.0440(7) Uani 1 1 d . . .
H22 H -1.0345 0.6986 0.7643 0.053 Uiso 1 1 calc R . .
C23 C -0.8114(5) 0.5276(3) 0.75838(6) 0.0390(6) Uani 1 1 d . . .
H23 H -0.8876 0.5019 0.7356 0.047 Uiso 1 1 calc R . .
C24 C -0.6131(5) 0.4485(2) 0.77433(6) 0.0340(6) Uani 1 1 d . . .
H24 H -0.5528 0.3690 0.7624 0.041 Uiso 1 1 calc R . .
H1 H -0.238(5) 0.328(2) 0.8072(6) 0.045(7) Uiso 1 1 d . . .


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

# MOLECULAR GEOMETRY

_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
N1 C1 1.334(3) . ?
N1 C19 1.411(3) . ?
N1 H1 0.94(2) . ?
O1 C1 1.352(2) . ?
O1 C4 1.405(2) . ?
O2 C3 1.356(2) . ?
O2 C7 1.398(2) . ?
O3 C5 1.232(3) . ?
O4 C12 1.248(2) . ?
C1 C2 1.408(3) . ?
C2 C3 1.424(3) . ?
C2 C12 1.443(3) . ?
C3 C4 1.350(3) . ?
C4 C5 1.414(3) . ?
C5 C6 1.488(3) . ?
C6 C7 1.396(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.369(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.485(3) . ?
C13 C14 1.382(3) . ?
C13 C18 1.392(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.385(3) . ?
C19 C24 1.390(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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
C1 N1 C19 131.2(2) . . ?
C1 N1 H1 110.9(15) . . ?
C19 N1 H1 117.5(15) . . ?
C1 O1 C4 105.64(16) . . ?
C3 O2 C7 115.62(16) . . ?
N1 C1 O1 119.82(19) . . ?
N1 C1 C2 127.5(2) . . ?
O1 C1 C2 112.68(18) . . ?
C1 C2 C3 102.49(19) . . ?
C1 C2 C12 121.28(19) . . ?
C3 C2 C12 136.0(2) . . ?
C4 C3 O2 123.02(19) . . ?
C4 C3 C2 110.20(19) . . ?
O2 C3 C2 126.76(19) . . ?
C3 C4 O1 108.94(18) . . ?
C3 C4 C5 127.1(2) . . ?
O1 C4 C5 123.94(19) . . ?
O3 C5 C4 126.8(2) . . ?
O3 C5 C6 123.76(19) . . ?
C4 C5 C6 109.49(19) . . ?
C7 C6 C11 117.6(2) . . ?
C7 C6 C5 121.81(19) . . ?
C11 C6 C5 120.56(19) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 O2 114.97(18) . . ?
C6 C7 O2 122.92(19) . . ?
C9 C8 C7 118.2(2) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O4 C12 C2 119.68(19) . . ?
O4 C12 C13 118.46(19) . . ?
C2 C12 C13 121.87(18) . . ?
C14 C13 C18 119.3(2) . . ?
C14 C13 C12 117.74(19) . . ?
C18 C13 C12 122.8(2) . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.1(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C24 119.4(2) . . ?
C20 C19 N1 123.9(2) . . ?
C24 C19 N1 116.6(2) . . ?
C21 C20 C19 119.3(2) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 119.0(2) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C19 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?

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 N1 C1 O1 1.1(4) . . . . ?
C19 N1 C1 C2 -178.7(2) . . . . ?
C4 O1 C1 N1 -177.78(19) . . . . ?
C4 O1 C1 C2 2.1(2) . . . . ?
N1 C1 C2 C3 177.9(2) . . . . ?
O1 C1 C2 C3 -1.9(2) . . . . ?
N1 C1 C2 C12 2.7(4) . . . . ?
O1 C1 C2 C12 -177.17(18) . . . . ?
C7 O2 C3 C4 2.4(3) . . . . ?
C7 O2 C3 C2 -179.3(2) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C12 C2 C3 C4 175.2(2) . . . . ?
C1 C2 C3 O2 -177.4(2) . . . . ?
C12 C2 C3 O2 -3.3(4) . . . . ?
O2 C3 C4 O1 178.67(18) . . . . ?
C2 C3 C4 O1 0.2(3) . . . . ?
O2 C3 C4 C5 -1.8(4) . . . . ?
C2 C3 C4 C5 179.7(2) . . . . ?
C1 O1 C4 C3 -1.3(2) . . . . ?
C1 O1 C4 C5 179.1(2) . . . . ?
C3 C4 C5 O3 179.9(2) . . . . ?
O1 C4 C5 O3 -0.6(4) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
O1 C4 C5 C6 179.55(19) . . . . ?
O3 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
O3 C5 C6 C11 2.1(3) . . . . ?
C4 C5 C6 C11 -178.0(2) . . . . ?
C11 C6 C7 C8 -1.0(3) . . . . ?
C5 C6 C7 C8 -179.8(2) . . . . ?
C11 C6 C7 O2 178.8(2) . . . . ?
C5 C6 C7 O2 -0.1(3) . . . . ?
C3 O2 C7 C8 178.23(19) . . . . ?
C3 O2 C7 C6 -1.6(3) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
O2 C7 C8 C9 -178.71(19) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C6 0.3(4) . . . . ?
C7 C6 C11 C10 0.3(3) . . . . ?
C5 C6 C11 C10 179.1(2) . . . . ?
C1 C2 C12 O4 8.5(3) . . . . ?
C3 C2 C12 O4 -164.8(2) . . . . ?
C1 C2 C12 C13 -171.5(2) . . . . ?
C3 C2 C12 C13 15.2(4) . . . . ?
O4 C12 C13 C14 32.8(3) . . . . ?
C2 C12 C13 C14 -147.2(2) . . . . ?
O4 C12 C13 C18 -143.0(2) . . . . ?
C2 C12 C13 C18 37.0(3) . . . . ?
C18 C13 C14 C15 -2.1(4) . . . . ?
C12 C13 C14 C15 -178.0(2) . . . . ?
C13 C14 C15 C16 2.0(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C16 C17 C18 C13 0.8(4) . . . . ?
C14 C13 C18 C17 0.7(4) . . . . ?
C12 C13 C18 C17 176.4(2) . . . . ?
C1 N1 C19 C20 -0.4(4) . . . . ?
C1 N1 C19 C24 179.9(2) . . . . ?
C24 C19 C20 C21 -0.7(4) . . . . ?
N1 C19 C20 C21 179.6(2) . . . . ?
C19 C20 C21 C22 0.5(4) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C22 C23 C24 C19 0.4(4) . . . . ?
C20 C19 C24 C23 0.3(4) . . . . ?
N1 C19 C24 C23 180.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049

#=====================  End of is_is411 =================================

#=====================  End of CIF submission =================================

_database_code_depnum_ccdc_archive 'CCDC 982677'
