# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2008

data_global

_journal_coden_Cambridge         440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Ulrich J Griesser'
'Doris E. Braun'
'Thomas Gelbrich'
'Volker Kahlenberg'
'Gerhard Laus'
'Josef Wieser'

_publ_contact_author_name        'Ulrich J Griesser'
_publ_contact_author_email       ULRICH.GRIESSER@UIBK.AC.AT

_publ_section_title              
;
Packing Polymorphism of a Conformationally Flexible
Molecule (Aprepitant)
;
_publ_requested_category         FO

# Attachment 'B805438J_Aprepitant.cif'

data_formI
_database_code_depnum_ccdc_archive 'CCDC 687301'

_audit_creation_date             2008-02-05T08:03:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            'aprepitant, form I'
_chemical_formula_moiety         'C23 H21 F7 N4 O3'
_chemical_formula_sum            'C23 H21 F7 N4 O3'
_chemical_formula_weight         534.44
_chemical_melting_point          526.5
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.421(4)
_cell_length_b                   7.710(4)
_cell_length_c                   42.200(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2414.5(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20507
_cell_measurement_theta_min      1.45
_cell_measurement_theta_max      27.36

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_number            17601
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         26.79
_diffrn_reflns_theta_full        26.79
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_reflns_number_total             2894
_reflns_number_gt                2536
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The anisotropic displacement parameters of the six disordered -CF3 fluorine
atoms attached to C(23) were restrained to being approximately isotropic,
using the ISOR command in SHELXL with a standard uncertainty of 0.008.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0962P)^2^+0.0177P] where P=(Fo^2^+2Fc^2^)/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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.103(11)
_refine_ls_number_reflns         2894
_refine_ls_number_parameters     372
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.262
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.2
_refine_diff_density_rms         0.047

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.3191(3) 0.7313(3) 0.07189(5) 0.0489(5) Uani 1 1 d . . .
N2 N 0.4150(3) 0.4373(3) 0.01414(5) 0.0522(5) Uani 1 1 d . . .
N3 N 0.7039(3) 0.4346(3) 0.01345(6) 0.0526(5) Uani 1 1 d . . .
N4 N 0.6558(3) 0.5943(3) 0.02589(5) 0.0517(5) Uani 1 1 d . . .
H2A H 0.293(5) 0.402(6) 0.0117(9) 0.066(10) Uiso 1 1 d . . .
H3 H 0.828(6) 0.395(6) 0.0117(10) 0.078(12) Uiso 1 1 d . . .
O1 O 0.3169(3) 0.5840(3) 0.13384(5) 0.0631(6) Uani 1 1 d . . .
O2 O 0.5590(2) 0.1853(3) -0.00477(5) 0.0610(5) Uani 1 1 d . . .
O3 O 0.3199(3) 0.8862(3) 0.13393(4) 0.0556(5) Uani 1 1 d . . .
F1 F 0.6618(5) 1.5346(3) 0.18832(7) 0.1006(8) Uani 1 1 d . . .
F2 F 0.9164(3) 1.4155(4) 0.17965(7) 0.0972(8) Uani 1 1 d . . .
F3 F 0.7172(4) 1.4214(3) 0.14351(5) 0.0840(7) Uani 1 1 d . . .
F4 F 0.9214(18) 0.866(2) 0.2465(3) 0.096(3) Uani 0.45(2) 1 d PU A 1
F5 F 0.787(3) 1.0384(17) 0.2759(3) 0.117(4) Uani 0.45(2) 1 d PU A 1
F6 F 0.6689(17) 0.793(2) 0.2642(3) 0.112(4) Uani 0.45(2) 1 d PU A 1
F4A F 0.9338(14) 0.941(2) 0.2544(3) 0.111(3) Uani 0.55(2) 1 d PU A 2
F5A F 0.697(2) 0.9834(18) 0.27995(15) 0.109(3) Uani 0.55(2) 1 d PU A 2
F6A F 0.726(2) 0.7487(12) 0.2559(3) 0.108(3) Uani 0.55(2) 1 d PU A 2
F7 F 0.9384(5) 1.3085(5) 0.07614(6) 0.1274(14) Uani 1 1 d . . .
C1 C 0.4794(3) 0.7390(4) 0.09243(6) 0.0490(6) Uani 1 1 d . . .
H1 H 0.5528 0.6325 0.0884 0.059 Uiso 1 1 calc R . .
C2 C 0.4188(4) 0.7346(4) 0.12731(6) 0.0529(6) Uani 1 1 d . . .
H2 H 0.5286 0.7336 0.141 0.063 Uiso 1 1 calc R . .
C3 C 0.1588(4) 0.5769(5) 0.11426(7) 0.0659(8) Uani 1 1 d . . .
H3B H 0.081 0.6782 0.1188 0.079 Uiso 1 1 calc R . .
H3A H 0.0896 0.4705 0.1191 0.079 Uiso 1 1 calc R . .
C4 C 0.2113(4) 0.5772(4) 0.07950(7) 0.0575(7) Uani 1 1 d . . .
H4B H 0.2818 0.4714 0.0747 0.069 Uiso 1 1 calc R . .
H4A H 0.1013 0.5759 0.0662 0.069 Uiso 1 1 calc R . .
C5 C 0.3643(4) 0.7378(4) 0.03799(6) 0.0503(6) Uani 1 1 d . . .
H5B H 0.4274 0.8485 0.0337 0.06 Uiso 1 1 calc R . .
H5A H 0.2506 0.739 0.0257 0.06 Uiso 1 1 calc R . .
C6 C 0.4796(3) 0.5919(4) 0.02589(6) 0.0494(6) Uani 1 1 d . . .
C7 C 0.5599(3) 0.3364(4) 0.00635(6) 0.0521(6) Uani 1 1 d . . .
C8 C 0.5974(4) 0.8937(4) 0.08631(6) 0.0514(6) Uani 1 1 d . . .
C9 C 0.7824(4) 0.8693(6) 0.08454(8) 0.0672(8) Uani 1 1 d . . .
H9 H 0.8293 0.7547 0.0856 0.081 Uiso 1 1 calc R . .
C10 C 0.9008(5) 1.0072(8) 0.08134(9) 0.0853(13) Uani 1 1 d . . .
H10 H 1.0275 0.9901 0.0806 0.102 Uiso 1 1 calc R . .
C11 C 0.8263(7) 1.1695(7) 0.07933(8) 0.0850(13) Uani 1 1 d . . .
C12 C 0.6449(6) 1.2006(5) 0.08022(8) 0.0757(10) Uani 1 1 d . . .
H12 H 0.5995 1.3153 0.0783 0.091 Uiso 1 1 calc R . .
C13 C 0.5284(5) 1.0612(4) 0.08397(7) 0.0613(7) Uani 1 1 d . . .
H13 H 0.402 1.08 0.0849 0.074 Uiso 1 1 calc R . .
C14 C 0.2891(4) 0.9134(5) 0.16712(7) 0.0659(8) Uani 1 1 d . . .
H14 H 0.2632 0.7994 0.1775 0.079 Uiso 1 1 calc R . .
C15 C 0.4519(4) 0.9947(5) 0.18273(6) 0.0572(7) Uani 1 1 d . . .
C16 C 0.5230(4) 1.1499(4) 0.17113(7) 0.0578(7) Uani 1 1 d . . .
H16 H 0.4726 1.2013 0.1527 0.069 Uiso 1 1 calc R . .
C17 C 0.6662(4) 1.2293(4) 0.18631(7) 0.0557(6) Uani 1 1 d . . .
C18 C 0.7414(4) 1.1562(5) 0.21344(7) 0.0572(7) Uani 1 1 d . . .
H18 H 0.8381 1.2118 0.2241 0.069 Uiso 1 1 calc R . .
C19 C 0.6726(4) 1.0014(5) 0.22452(7) 0.0586(7) Uani 1 1 d . A .
C20 C 0.5288(4) 0.9207(4) 0.20951(7) 0.0593(7) Uani 1 1 d . . .
H20 H 0.4828 0.8146 0.2176 0.071 Uiso 1 1 calc R . .
C21 C 0.1236(5) 1.0285(8) 0.16962(10) 0.0944(16) Uani 1 1 d . . .
H21C H 0.0199 0.9689 0.1603 0.142 Uiso 1 1 calc R . .
H21B H 0.1453 1.1374 0.1582 0.142 Uiso 1 1 calc R . .
H21A H 0.0989 1.0536 0.192 0.142 Uiso 1 1 calc R . .
C22 C 0.7396(5) 1.3984(5) 0.17461(8) 0.0643(8) Uani 1 1 d . . .
C23 C 0.7595(5) 0.9196(6) 0.25296(8) 0.0724(9) Uani 1 1 d U . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0445(9) 0.0528(13) 0.0493(10) -0.0047(9) -0.0005(8) -0.0040(9)
N2 0.0441(10) 0.0533(14) 0.0593(12) -0.0098(10) -0.0012(9) -0.0001(9)
N3 0.0467(10) 0.0548(14) 0.0565(11) -0.0095(10) 0.0034(9) -0.0035(9)
N4 0.0477(10) 0.0532(14) 0.0543(11) -0.0041(9) 0.0043(9) -0.0021(10)
O1 0.0689(12) 0.0627(14) 0.0576(10) 0.0045(9) -0.0015(9) -0.0153(11)
O2 0.0483(9) 0.0582(13) 0.0764(12) -0.0185(10) -0.0014(9) 0.0014(9)
O3 0.0548(10) 0.0624(13) 0.0497(9) -0.0077(8) 0.0003(8) -0.0009(9)
F1 0.147(2) 0.0541(14) 0.1009(16) -0.0067(11) 0.0197(17) 0.0051(15)
F2 0.0837(14) 0.0896(18) 0.1184(18) 0.0300(14) -0.0249(13) -0.0258(13)
F3 0.1127(16) 0.0719(15) 0.0673(11) 0.0097(9) -0.0089(11) -0.0146(13)
F4 0.080(5) 0.120(7) 0.086(4) 0.025(4) 0.000(3) 0.041(5)
F5 0.160(8) 0.120(6) 0.072(4) -0.007(4) -0.045(5) 0.009(6)
F6 0.106(5) 0.124(8) 0.107(6) 0.063(5) -0.009(4) -0.024(5)
F4A 0.078(3) 0.137(7) 0.117(6) 0.048(5) -0.026(4) -0.002(4)
F5A 0.136(6) 0.136(6) 0.054(2) 0.005(3) 0.003(3) 0.041(5)
F6A 0.145(7) 0.083(4) 0.096(4) 0.019(3) -0.027(4) 0.011(4)
F7 0.164(3) 0.129(3) 0.0892(15) 0.0053(15) -0.0049(17) -0.106(2)
C1 0.0453(11) 0.0490(15) 0.0527(12) -0.0008(10) -0.0027(9) -0.0023(11)
C2 0.0552(13) 0.0501(16) 0.0533(13) 0.0002(10) -0.0011(11) -0.0044(12)
C3 0.0612(15) 0.078(2) 0.0591(15) -0.0060(14) 0.0069(12) -0.0206(16)
C4 0.0567(14) 0.0597(18) 0.0562(14) -0.0046(12) 0.0043(11) -0.0154(13)
C5 0.0494(12) 0.0501(15) 0.0513(12) -0.0041(10) -0.0006(9) 0.0003(11)
C6 0.0495(11) 0.0508(15) 0.0480(11) -0.0025(10) 0.0021(9) -0.0025(11)
C7 0.0455(12) 0.0549(16) 0.0560(12) -0.0085(11) 0.0010(10) -0.0011(11)
C8 0.0489(12) 0.0541(16) 0.0511(12) -0.0027(10) -0.0019(10) -0.0054(11)
C9 0.0531(14) 0.080(2) 0.0688(16) -0.0066(15) -0.0003(13) -0.0103(15)
C10 0.0634(18) 0.116(4) 0.077(2) -0.008(2) 0.0019(16) -0.035(2)
C11 0.101(3) 0.092(3) 0.0619(17) 0.0028(17) -0.0045(18) -0.056(3)
C12 0.111(3) 0.056(2) 0.0598(16) 0.0021(13) -0.0078(17) -0.0240(19)
C13 0.0725(17) 0.0510(17) 0.0605(14) -0.0002(12) -0.0017(13) -0.0044(14)
C14 0.0590(15) 0.085(2) 0.0541(14) -0.0147(14) 0.0067(12) -0.0116(16)
C15 0.0574(14) 0.0645(18) 0.0497(12) -0.0094(12) 0.0044(11) -0.0007(13)
C16 0.0587(14) 0.0599(18) 0.0548(13) -0.0030(12) -0.0036(11) 0.0010(13)
C17 0.0586(13) 0.0543(17) 0.0542(13) -0.0036(11) -0.0026(11) 0.0034(13)
C18 0.0542(13) 0.0622(19) 0.0552(13) -0.0044(12) -0.0040(11) 0.0034(12)
C19 0.0578(14) 0.0647(19) 0.0532(13) 0.0016(12) 0.0002(11) 0.0055(14)
C20 0.0618(14) 0.0616(19) 0.0544(13) -0.0038(12) 0.0055(12) -0.0010(14)
C21 0.0546(16) 0.143(4) 0.085(2) -0.045(3) 0.0055(16) 0.004(2)
C22 0.0718(17) 0.057(2) 0.0642(16) -0.0009(13) -0.0107(14) -0.0004(14)
C23 0.0716(18) 0.083(3) 0.0626(16) 0.0116(16) -0.0020(14) 0.0051(18)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C4 1.468(4) . ?
N1 C5 1.470(3) . ?
N1 C1 1.473(3) . ?
N2 C7 1.367(4) . ?
N2 C6 1.377(4) . ?
N3 C7 1.344(4) . ?
N3 N4 1.385(4) . ?
N4 C6 1.308(3) . ?
O1 C2 1.413(4) . ?
O1 C3 1.436(4) . ?
O2 C7 1.256(4) . ?
O3 C2 1.408(4) . ?
O3 C14 1.435(3) . ?
F1 C22 1.331(4) . ?
F2 C22 1.336(4) . ?
F3 C22 1.335(4) . ?
F4 C23 1.300(11) . ?
F5 C23 1.347(10) . ?
F6 C23 1.277(11) . ?
F4A C23 1.306(10) . ?
F5A C23 1.324(8) . ?
F6A C23 1.346(11) . ?
F7 C11 1.363(4) . ?
C1 C8 1.502(4) . ?
C1 C2 1.540(4) . ?
C3 C4 1.518(4) . ?
C5 C6 1.502(4) . ?
C8 C9 1.388(4) . ?
C8 C13 1.393(5) . ?
C9 C10 1.386(6) . ?
C10 C11 1.370(8) . ?
C11 C12 1.368(7) . ?
C12 C13 1.388(5) . ?
C14 C15 1.512(4) . ?
C14 C21 1.519(5) . ?
C15 C20 1.388(4) . ?
C15 C16 1.396(5) . ?
C16 C17 1.384(4) . ?
C17 C18 1.393(4) . ?
C17 C22 1.497(5) . ?
C18 C19 1.380(5) . ?
C19 C20 1.388(5) . ?
C19 C23 1.501(4) . ?

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
C4 N1 C5 111.4(2) . . ?
C4 N1 C1 110.1(2) . . ?
C5 N1 C1 112.73(19) . . ?
C7 N2 C6 107.8(2) . . ?
C7 N3 N4 112.4(2) . . ?
C6 N4 N3 104.2(2) . . ?
C2 O1 C3 110.9(2) . . ?
C2 O3 C14 113.5(2) . . ?
N1 C1 C8 113.7(2) . . ?
N1 C1 C2 109.0(2) . . ?
C8 C1 C2 110.6(2) . . ?
O3 C2 O1 111.4(2) . . ?
O3 C2 C1 108.9(2) . . ?
O1 C2 C1 111.1(2) . . ?
O1 C3 C4 110.2(2) . . ?
N1 C4 C3 110.6(2) . . ?
N1 C5 C6 115.8(2) . . ?
N4 C6 N2 111.1(3) . . ?
N4 C6 C5 124.0(3) . . ?
N2 C6 C5 124.9(2) . . ?
O2 C7 N3 127.6(3) . . ?
O2 C7 N2 127.8(2) . . ?
N3 C7 N2 104.5(2) . . ?
C9 C8 C13 119.1(3) . . ?
C9 C8 C1 118.6(3) . . ?
C13 C8 C1 122.3(2) . . ?
C10 C9 C8 121.9(4) . . ?
C11 C10 C9 116.8(4) . . ?
F7 C11 C12 117.7(5) . . ?
F7 C11 C10 118.5(4) . . ?
C12 C11 C10 123.7(3) . . ?
C11 C12 C13 118.7(4) . . ?
C12 C13 C8 119.8(3) . . ?
O3 C14 C15 111.0(2) . . ?
O3 C14 C21 106.4(3) . . ?
C15 C14 C21 111.9(3) . . ?
C20 C15 C16 118.8(3) . . ?
C20 C15 C14 120.8(3) . . ?
C16 C15 C14 120.3(3) . . ?
C17 C16 C15 120.4(3) . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 C22 120.8(3) . . ?
C18 C17 C22 118.6(3) . . ?
C19 C18 C17 118.7(3) . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 C23 118.4(3) . . ?
C20 C19 C23 120.4(3) . . ?
C15 C20 C19 120.2(3) . . ?
F1 C22 F3 105.6(3) . . ?
F1 C22 F2 106.2(3) . . ?
F3 C22 F2 105.4(3) . . ?
F1 C22 C17 112.7(3) . . ?
F3 C22 C17 113.3(3) . . ?
F2 C22 C17 113.0(3) . . ?
F6 C23 F4 108.7(8) . . ?
F6 C23 F4A 126.9(7) . . ?
F4 C23 F4A 30.0(6) . . ?
F6 C23 F5A 77.4(7) . . ?
F4 C23 F5A 128.3(6) . . ?
F4A C23 F5A 104.9(7) . . ?
F6 C23 F6A 28.5(7) . . ?
F4 C23 F6A 82.8(7) . . ?
F4A C23 F6A 107.4(7) . . ?
F5A C23 F6A 102.8(6) . . ?
F6 C23 F5 109.5(8) . . ?
F4 C23 F5 103.2(7) . . ?
F4A C23 F5 74.5(7) . . ?
F5A C23 F5 35.1(5) . . ?
F6A C23 F5 128.8(7) . . ?
F6 C23 C19 113.0(6) . . ?
F4 C23 C19 111.3(5) . . ?
F4A C23 C19 114.3(5) . . ?
F5A C23 C19 112.5(4) . . ?
F6A C23 C19 114.0(5) . . ?
F5 C23 C19 110.7(6) . . ?

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
C7 N3 N4 C6 -0.7(3) . . . . ?
C4 N1 C1 C8 -179.8(2) . . . . ?
C5 N1 C1 C8 55.2(3) . . . . ?
C4 N1 C1 C2 -55.9(3) . . . . ?
C5 N1 C1 C2 179.1(2) . . . . ?
C14 O3 C2 O1 69.4(3) . . . . ?
C14 O3 C2 C1 -167.7(2) . . . . ?
C3 O1 C2 O3 61.9(3) . . . . ?
C3 O1 C2 C1 -59.7(3) . . . . ?
N1 C1 C2 O3 -65.1(3) . . . . ?
C8 C1 C2 O3 60.6(3) . . . . ?
N1 C1 C2 O1 57.9(3) . . . . ?
C8 C1 C2 O1 -176.4(2) . . . . ?
C2 O1 C3 C4 59.1(3) . . . . ?
C5 N1 C4 C3 -177.4(2) . . . . ?
C1 N1 C4 C3 56.7(3) . . . . ?
O1 C3 C4 N1 -57.5(4) . . . . ?
C4 N1 C5 C6 -63.0(3) . . . . ?
C1 N1 C5 C6 61.4(3) . . . . ?
N3 N4 C6 N2 0.3(3) . . . . ?
N3 N4 C6 C5 178.8(2) . . . . ?
C7 N2 C6 N4 0.2(3) . . . . ?
C7 N2 C6 C5 -178.4(3) . . . . ?
N1 C5 C6 N4 -88.9(3) . . . . ?
N1 C5 C6 N2 89.4(3) . . . . ?
N4 N3 C7 O2 -178.9(3) . . . . ?
N4 N3 C7 N2 0.8(3) . . . . ?
C6 N2 C7 O2 179.1(3) . . . . ?
C6 N2 C7 N3 -0.5(3) . . . . ?
N1 C1 C8 C9 -135.1(3) . . . . ?
C2 C1 C8 C9 101.9(3) . . . . ?
N1 C1 C8 C13 48.2(4) . . . . ?
C2 C1 C8 C13 -74.8(3) . . . . ?
C13 C8 C9 C10 1.7(5) . . . . ?
C1 C8 C9 C10 -175.1(3) . . . . ?
C8 C9 C10 C11 -1.3(5) . . . . ?
C9 C10 C11 F7 -179.9(3) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
F7 C11 C12 C13 -179.0(3) . . . . ?
C10 C11 C12 C13 1.3(6) . . . . ?
C11 C12 C13 C8 -0.9(5) . . . . ?
C9 C8 C13 C12 -0.6(5) . . . . ?
C1 C8 C13 C12 176.1(3) . . . . ?
C2 O3 C14 C15 81.3(3) . . . . ?
C2 O3 C14 C21 -156.6(3) . . . . ?
O3 C14 C15 C20 -127.3(3) . . . . ?
C21 C14 C15 C20 114.0(4) . . . . ?
O3 C14 C15 C16 55.4(4) . . . . ?
C21 C14 C15 C16 -63.3(4) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
C14 C15 C16 C17 176.7(3) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C15 C16 C17 C22 -178.1(3) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C22 C17 C18 C19 179.2(3) . . . . ?
C17 C18 C19 C20 -1.4(4) . . . . ?
C17 C18 C19 C23 177.4(3) . . . . ?
C16 C15 C20 C19 0.6(4) . . . . ?
C14 C15 C20 C19 -176.8(3) . . . . ?
C18 C19 C20 C15 0.4(5) . . . . ?
C23 C19 C20 C15 -178.4(3) . . . . ?
C16 C17 C22 F1 91.4(4) . . . . ?
C18 C17 C22 F1 -86.5(4) . . . . ?
C16 C17 C22 F3 -28.4(4) . . . . ?
C18 C17 C22 F3 153.7(3) . . . . ?
C16 C17 C22 F2 -148.2(3) . . . . ?
C18 C17 C22 F2 33.9(4) . . . . ?
C18 C19 C23 F6 169.6(11) . . . . ?
C20 C19 C23 F6 -11.6(12) . . . . ?
C18 C19 C23 F4 -67.8(10) . . . . ?
C20 C19 C23 F4 111.0(10) . . . . ?
C18 C19 C23 F4A -35.4(11) . . . . ?
C20 C19 C23 F4A 143.5(10) . . . . ?
C18 C19 C23 F5A 84.1(10) . . . . ?
C20 C19 C23 F5A -97.0(10) . . . . ?
C18 C19 C23 F6A -159.4(8) . . . . ?
C20 C19 C23 F6A 19.5(9) . . . . ?
C18 C19 C23 F5 46.4(12) . . . . ?
C20 C19 C23 F5 -134.8(11) . . . . ?

#===END

data_formII
_database_code_depnum_ccdc_archive 'CCDC 687302'

_audit_creation_date             2008-02-05T19:08:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            'aprepitant, form II'
_chemical_melting_point          526
_chemical_formula_moiety         'C23 H21 F7 N4 O3'
_chemical_formula_sum            'C23 H21 F7 N4 O3'
_chemical_formula_weight         534.44
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

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

_cell_length_a                   7.7768(16)
_cell_length_b                   7.4072(11)
_cell_length_c                   21.297(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.861(17)
_cell_angle_gamma                90
_cell_volume                     1225.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6880
_cell_measurement_theta_min      1.91
_cell_measurement_theta_max      24.99

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.003
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_number            6918
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_reflns_number_total             6918
_reflns_number_gt                5441
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
The anisotropic displacement parameters of the -CF3 fluorine atoms were
restrained to being approximately isotropic, using the ISOR command in SHELXL
with a standard uncertainty of 0.008. The chemically equivalent C-C bond
lengths in the bistrifluoromethyl substituted phenyl ring and the chemically
equivalent O1-C2 and O1-C3 bond distances in the morpholine ring were
restraint using the SHELXL SADI command with a standard uncertainty of 0.01.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+4.0349P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         6918
_refine_ls_number_parameters     337
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0903
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1775
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.1
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.069

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.4972(7) 0.8639(8) 0.3563(2) 0.0360(13) Uani 1 1 d U . .
N2 N 0.8084(7) 0.7664(7) 0.4714(3) 0.0356(14) Uani 1 1 d . . .
H2A H 0.8384 0.8806 0.4751 0.043 Uiso 1 1 calc R . .
N3 N 0.8105(7) 0.4748(7) 0.4731(2) 0.0332(13) Uani 1 1 d . . .
H3A H 0.8439 0.3624 0.4792 0.04 Uiso 1 1 calc R . .
N4 N 0.6488(7) 0.5255(7) 0.4483(3) 0.0373(14) Uani 1 1 d . . .
O1 O 0.6321(6) 0.8647(7) 0.23275(19) 0.0420(12) Uani 1 1 d D . .
O2 O 1.0636(5) 0.6220(6) 0.5099(2) 0.0445(13) Uani 1 1 d . . .
O3 O 0.3293(6) 0.8633(7) 0.23172(18) 0.0373(12) Uani 1 1 d U . .
F1 F -0.2040(6) 0.4582(8) 0.2112(2) 0.0755(15) Uani 1 1 d U . .
F2 F -0.2188(8) 0.2744(9) 0.1345(3) 0.113(2) Uani 1 1 d U . .
F3 F -0.3294(6) 0.5399(9) 0.1248(3) 0.0863(18) Uani 1 1 d U . .
F4 F 0.1533(7) 0.4359(9) -0.0594(2) 0.0940(19) Uani 1 1 d U . .
F5 F 0.4050(8) 0.5006(10) -0.0268(3) 0.113(2) Uani 1 1 d U . .
F6 F 0.2911(9) 0.2552(8) -0.0025(3) 0.104(2) Uani 1 1 d U . .
F7 F -0.0828(8) 0.2486(9) 0.3481(3) 0.106(2) Uani 1 1 d U . .
C1 C 0.4842(8) 0.7036(9) 0.3154(3) 0.0344(16) Uani 1 1 d . . .
H1A H 0.5906 0.6299 0.3239 0.041 Uiso 1 1 calc R . .
C2 C 0.4810(8) 0.7622(10) 0.2465(3) 0.0383(16) Uani 1 1 d D . .
H2B H 0.478 0.6512 0.2198 0.046 Uiso 1 1 calc R . .
C3 C 0.6431(10) 1.0221(9) 0.2723(3) 0.0474(19) Uani 1 1 d DU . .
H3B H 0.5416 1.0999 0.2627 0.057 Uiso 1 1 calc R . .
H3C H 0.7473 1.0917 0.2628 0.057 Uiso 1 1 calc R . .
C4 C 0.6506(8) 0.9741(10) 0.3416(3) 0.0376(16) Uani 1 1 d . . .
H4B H 0.757 0.9049 0.3523 0.045 Uiso 1 1 calc R . .
H4C H 0.6533 1.0858 0.3671 0.045 Uiso 1 1 calc R . .
C5 C 0.5049(9) 0.8187(9) 0.4232(3) 0.0355(16) Uani 1 1 d . . .
H5A H 0.3952 0.7588 0.4324 0.043 Uiso 1 1 calc R . .
H5B H 0.5096 0.9334 0.4471 0.043 Uiso 1 1 calc R . .
C6 C 0.6478(8) 0.7022(9) 0.4487(3) 0.0311(15) Uani 1 1 d . . .
C7 C 0.9102(8) 0.6218(9) 0.4867(3) 0.0342(15) Uani 1 1 d . . .
C8 C 0.3319(7) 0.5846(7) 0.3271(3) 0.0327(16) Uani 1 1 d D . .
C9 C 0.3581(9) 0.3991(7) 0.3315(3) 0.048(2) Uani 1 1 d D . .
H9A H 0.4711 0.3516 0.3293 0.058 Uiso 1 1 calc R . .
C10 C 0.2202(10) 0.2824(10) 0.3390(4) 0.070(3) Uani 1 1 d D . .
H10A H 0.2371 0.1557 0.3427 0.084 Uiso 1 1 calc R . .
C11 C 0.0576(10) 0.3578(10) 0.3410(4) 0.061(2) Uani 1 1 d DU . .
C12 C 0.0280(9) 0.5416(10) 0.3384(4) 0.063(2) Uani 1 1 d DU . .
H12A H -0.085 0.5886 0.3412 0.075 Uiso 1 1 calc R . .
C13 C 0.1675(7) 0.6566(8) 0.3315(3) 0.0356(17) Uani 1 1 d D . .
H13A H 0.1507 0.7836 0.3298 0.043 Uiso 1 1 calc R . .
C14 C 0.2985(10) 0.8973(10) 0.1641(3) 0.0456(19) Uani 1 1 d U . .
H14A H 0.4105 0.9201 0.1444 0.055 Uiso 1 1 calc R . .
C15 C 0.2091(7) 0.7319(8) 0.1332(2) 0.0351(17) Uani 1 1 d D . .
C16 C 0.0578(8) 0.6615(8) 0.1560(3) 0.0424(18) Uani 1 1 d D . .
H16A H 0.0127 0.7103 0.193 0.051 Uiso 1 1 calc R . .
C17 C -0.0271(8) 0.5199(8) 0.1246(3) 0.0389(17) Uani 1 1 d D . .
C18 C 0.0391(8) 0.4467(9) 0.0708(3) 0.0428(18) Uani 1 1 d D . .
H18A H -0.0186 0.3496 0.0497 0.051 Uiso 1 1 calc R . .
C19 C 0.1909(8) 0.5163(8) 0.0479(3) 0.0396(17) Uani 1 1 d D . .
C20 C 0.2756(8) 0.6567(8) 0.0796(2) 0.0385(18) Uani 1 1 d D . .
H20A H 0.3802 0.702 0.0646 0.046 Uiso 1 1 calc R . .
C21 C 0.1877(13) 1.0662(10) 0.1597(4) 0.077(3) Uani 1 1 d . . .
H21A H 0.1641 1.0975 0.1154 0.116 Uiso 1 1 calc R . .
H21B H 0.2487 1.1661 0.1812 0.116 Uiso 1 1 calc R . .
H21C H 0.0789 1.0438 0.1797 0.116 Uiso 1 1 calc R . .
C22 C -0.1913(10) 0.4482(12) 0.1497(4) 0.057(2) Uani 1 1 d . . .
C23 C 0.2601(12) 0.4293(11) -0.0079(4) 0.059(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.031(3) 0.027(3) 0.049(3) -0.006(3) -0.003(2) 0.003(3)
N2 0.028(3) 0.021(3) 0.058(4) 0.000(3) -0.005(3) 0.001(3)
N3 0.034(3) 0.020(3) 0.045(3) 0.005(2) -0.008(3) -0.001(3)
N4 0.027(3) 0.032(4) 0.053(3) 0.007(3) -0.004(3) -0.002(3)
O1 0.031(3) 0.053(3) 0.042(3) -0.004(3) 0.005(2) -0.013(3)
O2 0.031(3) 0.026(2) 0.075(3) -0.006(3) -0.020(2) -0.001(2)
O3 0.043(3) 0.040(3) 0.027(2) 0.003(2) -0.0097(19) -0.005(3)
F1 0.055(3) 0.097(4) 0.075(3) 0.017(3) 0.007(2) -0.016(3)
F2 0.088(4) 0.093(4) 0.162(5) -0.045(4) 0.057(4) -0.033(4)
F3 0.045(3) 0.127(5) 0.086(3) 0.026(3) 0.004(2) 0.014(3)
F4 0.090(4) 0.119(5) 0.072(3) -0.010(3) -0.015(3) 0.004(3)
F5 0.091(4) 0.135(5) 0.117(4) -0.048(4) 0.050(3) -0.039(4)
F6 0.145(5) 0.080(4) 0.090(3) -0.014(3) 0.033(4) 0.045(4)
F7 0.099(4) 0.125(5) 0.095(4) -0.017(4) 0.014(3) -0.081(4)
C1 0.025(4) 0.031(4) 0.047(4) -0.003(3) -0.002(3) 0.003(3)
C2 0.029(4) 0.041(4) 0.046(4) 0.001(3) 0.007(3) -0.013(4)
C3 0.042(4) 0.038(4) 0.062(4) 0.004(3) -0.002(3) -0.020(4)
C4 0.025(3) 0.038(4) 0.048(4) 0.010(3) -0.004(3) -0.012(4)
C5 0.034(4) 0.034(4) 0.038(3) -0.001(3) -0.002(3) 0.005(3)
C6 0.026(4) 0.029(4) 0.038(3) 0.006(3) 0.003(3) -0.009(3)
C7 0.036(4) 0.025(3) 0.041(3) 0.011(3) -0.010(3) -0.013(3)
C8 0.039(4) 0.019(4) 0.040(4) 0.006(3) 0.000(3) -0.008(3)
C9 0.057(5) 0.037(5) 0.050(4) 0.000(3) -0.008(4) -0.023(4)
C10 0.098(8) 0.037(5) 0.073(6) -0.001(4) -0.023(6) -0.017(6)
C11 0.071(5) 0.063(5) 0.051(4) -0.005(4) 0.009(4) -0.037(5)
C12 0.042(4) 0.079(5) 0.067(5) -0.004(4) -0.008(4) -0.017(4)
C13 0.033(4) 0.035(4) 0.039(4) -0.004(3) 0.002(3) -0.012(3)
C14 0.053(4) 0.043(4) 0.040(3) 0.013(3) -0.009(3) -0.013(4)
C15 0.044(4) 0.035(4) 0.026(3) 0.008(3) -0.007(3) -0.014(3)
C16 0.042(4) 0.040(5) 0.044(4) -0.004(3) 0.001(3) 0.003(4)
C17 0.018(3) 0.045(4) 0.054(4) 0.004(4) -0.005(3) -0.003(3)
C18 0.043(4) 0.039(4) 0.045(4) -0.016(3) -0.009(3) 0.010(4)
C19 0.042(4) 0.036(4) 0.040(4) 0.004(3) -0.004(3) 0.006(4)
C20 0.036(4) 0.048(5) 0.032(3) 0.007(3) 0.000(3) -0.003(4)
C21 0.122(9) 0.034(5) 0.070(6) 0.003(4) -0.044(6) -0.009(5)
C22 0.041(5) 0.053(5) 0.079(6) -0.027(4) 0.001(4) -0.006(4)
C23 0.051(5) 0.046(5) 0.081(6) -0.004(4) 0.008(5) 0.004(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
N1 C5 1.460(8) . ?
N1 C1 1.474(8) . ?
N1 C4 1.492(8) . ?
N2 C7 1.362(8) . ?
N2 C6 1.400(8) . ?
N3 C7 1.360(8) . ?
N3 N4 1.391(7) . ?
N4 C6 1.309(7) . ?
O1 C3 1.438(7) . ?
O1 C2 1.442(6) . ?
O2 C7 1.268(7) . ?
O3 C2 1.419(8) . ?
O3 C14 1.470(7) . ?
F1 C22 1.320(9) . ?
F2 C22 1.342(9) . ?
F3 C22 1.356(9) . ?
F4 C23 1.342(10) . ?
F5 C23 1.324(10) . ?
F6 C23 1.317(9) . ?
F7 C11 1.373(8) . ?
C1 C8 1.507(9) . ?
C1 C2 1.529(9) . ?
C3 C4 1.517(9) . ?
C5 C6 1.488(9) . ?
C8 C9 1.391(6) . ?
C8 C13 1.392(6) . ?
C9 C10 1.393(6) . ?
C10 C11 1.385(6) . ?
C11 C12 1.382(6) . ?
C12 C13 1.393(6) . ?
C14 C21 1.519(10) . ?
C14 C15 1.540(9) . ?
C15 C20 1.392(6) . ?
C15 C16 1.396(6) . ?
C16 C17 1.392(6) . ?
C17 C18 1.389(6) . ?
C17 C22 1.505(10) . ?
C18 C19 1.398(6) . ?
C19 C20 1.388(6) . ?
C19 C23 1.478(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
C5 N1 C1 113.0(5) . . ?
C5 N1 C4 109.6(5) . . ?
C1 N1 C4 110.4(5) . . ?
C7 N2 C6 108.3(5) . . ?
C7 N3 N4 111.1(5) . . ?
C6 N4 N3 105.8(5) . . ?
C3 O1 C2 109.4(5) . . ?
C2 O3 C14 113.6(5) . . ?
N1 C1 C8 113.9(5) . . ?
N1 C1 C2 109.6(5) . . ?
C8 C1 C2 110.4(5) . . ?
O3 C2 O1 110.7(5) . . ?
O3 C2 C1 109.7(5) . . ?
O1 C2 C1 111.7(5) . . ?
O1 C3 C4 112.2(6) . . ?
N1 C4 C3 109.9(5) . . ?
N1 C5 C6 118.8(6) . . ?
N4 C6 N2 109.6(6) . . ?
N4 C6 C5 125.6(6) . . ?
N2 C6 C5 124.5(6) . . ?
O2 C7 N3 126.8(6) . . ?
O2 C7 N2 128.1(6) . . ?
N3 C7 N2 105.0(5) . . ?
C9 C8 C13 120.4(6) . . ?
C9 C8 C1 118.3(5) . . ?
C13 C8 C1 121.2(5) . . ?
C8 C9 C10 120.6(6) . . ?
C11 C10 C9 117.6(7) . . ?
F7 C11 C12 117.0(7) . . ?
F7 C11 C10 119.9(7) . . ?
C12 C11 C10 123.1(7) . . ?
C11 C12 C13 118.5(7) . . ?
C8 C13 C12 119.7(6) . . ?
O3 C14 C21 105.4(6) . . ?
O3 C14 C15 109.3(5) . . ?
C21 C14 C15 112.7(6) . . ?
C20 C15 C16 119.3(5) . . ?
C20 C15 C14 119.4(5) . . ?
C16 C15 C14 121.3(5) . . ?
C17 C16 C15 120.2(6) . . ?
C18 C17 C16 120.2(6) . . ?
C18 C17 C22 120.7(5) . . ?
C16 C17 C22 119.1(6) . . ?
C17 C18 C19 119.9(5) . . ?
C20 C19 C18 119.7(6) . . ?
C20 C19 C23 122.3(6) . . ?
C18 C19 C23 117.9(6) . . ?
C19 C20 C15 120.8(6) . . ?
F1 C22 F2 105.9(8) . . ?
F1 C22 F3 105.2(7) . . ?
F2 C22 F3 105.8(7) . . ?
F1 C22 C17 116.0(6) . . ?
F2 C22 C17 112.3(7) . . ?
F3 C22 C17 110.7(7) . . ?
F6 C23 F5 105.2(8) . . ?
F6 C23 F4 102.2(7) . . ?
F5 C23 F4 103.9(8) . . ?
F6 C23 C19 115.3(8) . . ?
F5 C23 C19 114.8(7) . . ?
F4 C23 C19 113.9(7) . . ?

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
C7 N3 N4 C6 -2.0(8) . . . . ?
C5 N1 C1 C8 57.0(7) . . . . ?
C4 N1 C1 C8 -179.9(5) . . . . ?
C5 N1 C1 C2 -178.7(5) . . . . ?
C4 N1 C1 C2 -55.6(6) . . . . ?
C14 O3 C2 O1 66.9(7) . . . . ?
C14 O3 C2 C1 -169.4(5) . . . . ?
C3 O1 C2 O3 63.7(6) . . . . ?
C3 O1 C2 C1 -58.9(7) . . . . ?
N1 C1 C2 O3 -64.9(6) . . . . ?
C8 C1 C2 O3 61.3(7) . . . . ?
N1 C1 C2 O1 58.2(7) . . . . ?
C8 C1 C2 O1 -175.5(5) . . . . ?
C2 O1 C3 C4 58.6(7) . . . . ?
C5 N1 C4 C3 -179.8(6) . . . . ?
C1 N1 C4 C3 55.2(7) . . . . ?
O1 C3 C4 N1 -57.1(8) . . . . ?
C1 N1 C5 C6 59.3(8) . . . . ?
C4 N1 C5 C6 -64.2(8) . . . . ?
N3 N4 C6 N2 2.0(8) . . . . ?
N3 N4 C6 C5 176.4(6) . . . . ?
C7 N2 C6 N4 -1.4(8) . . . . ?
C7 N2 C6 C5 -175.9(6) . . . . ?
N1 C5 C6 N4 -85.3(9) . . . . ?
N1 C5 C6 N2 88.3(8) . . . . ?
N4 N3 C7 O2 180.0(6) . . . . ?
N4 N3 C7 N2 1.2(7) . . . . ?
C6 N2 C7 O2 -178.7(6) . . . . ?
C6 N2 C7 N3 0.1(7) . . . . ?
N1 C1 C8 C9 -134.0(6) . . . . ?
C2 C1 C8 C9 102.2(7) . . . . ?
N1 C1 C8 C13 48.1(8) . . . . ?
C2 C1 C8 C13 -75.8(7) . . . . ?
C13 C8 C9 C10 1.3(11) . . . . ?
C1 C8 C9 C10 -176.7(6) . . . . ?
C8 C9 C10 C11 1.0(11) . . . . ?
C9 C10 C11 F7 179.7(7) . . . . ?
C9 C10 C11 C12 -2.7(13) . . . . ?
F7 C11 C12 C13 179.7(6) . . . . ?
C10 C11 C12 C13 2.1(13) . . . . ?
C9 C8 C13 C12 -2.0(10) . . . . ?
C1 C8 C13 C12 176.0(6) . . . . ?
C11 C12 C13 C8 0.3(11) . . . . ?
C2 O3 C14 C21 -155.6(6) . . . . ?
C2 O3 C14 C15 83.0(7) . . . . ?
O3 C14 C15 C20 -129.5(6) . . . . ?
C21 C14 C15 C20 113.7(8) . . . . ?
O3 C14 C15 C16 53.7(8) . . . . ?
C21 C14 C15 C16 -63.1(9) . . . . ?
C20 C15 C16 C17 -1.3(10) . . . . ?
C14 C15 C16 C17 175.5(6) . . . . ?
C15 C16 C17 C18 0.7(10) . . . . ?
C15 C16 C17 C22 -179.2(7) . . . . ?
C16 C17 C18 C19 -0.4(10) . . . . ?
C22 C17 C18 C19 179.4(7) . . . . ?
C17 C18 C19 C20 0.8(10) . . . . ?
C17 C18 C19 C23 177.6(7) . . . . ?
C18 C19 C20 C15 -1.5(9) . . . . ?
C23 C19 C20 C15 -178.1(7) . . . . ?
C16 C15 C20 C19 1.7(9) . . . . ?
C14 C15 C20 C19 -175.2(6) . . . . ?
C18 C17 C22 F1 149.3(7) . . . . ?
C16 C17 C22 F1 -30.8(11) . . . . ?
C18 C17 C22 F2 27.3(11) . . . . ?
C16 C17 C22 F2 -152.9(7) . . . . ?
C18 C17 C22 F3 -90.8(8) . . . . ?
C16 C17 C22 F3 89.0(8) . . . . ?
C20 C19 C23 F6 120.0(8) . . . . ?
C18 C19 C23 F6 -56.7(10) . . . . ?
C20 C19 C23 F5 -2.6(11) . . . . ?
C18 C19 C23 F5 -179.4(7) . . . . ?
C20 C19 C23 F4 -122.2(8) . . . . ?
C18 C19 C23 F4 61.0(9) . . . . ?

# start Validation Reply Form
_vrf_PLAT029_ALERT_3_A           
;
PROBLEM: _diffrn_measured_fraction_theta_full low ....... 0.93
RESPONS: The very small non-merohedral twinned form II single crystals
showed no scattering at higher diffraction angles
;

#===END