# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


# Attachment '- Form VI_vorinostat_31-10-2011.CIF'

##############################################################################
### CIF submission form for results of Rietveld refinements (IUCr journals)###
### Version 10 February 2005 ###
##############################################################################

# This is an electronic "form" for submitting the results of a Rietveld
# refinement of a model against powder diffraction data to an
# IUCr journal as a Crystallographic Information File (CIF). Full details
# of the CIF format are given in the paper "The Crystallographic Information
# File (CIF): a New Standard Archive File for Crystallography" by S. R. Hall,
# F. H. Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].
#
# The current version of the powder CIF dictionary, which contains definitions
# of the terms staring _pd_, may be obtained from
# http://www.iucr.org/iucr-top/cif/pd/index.html. Other terms are defined in
# the core CIF dictionary at http://www.iucr.org/iucr-top/cif/core/index.html.
#
# Note that all fields should be numeric or character type EXCEPT those which
# are flagged as 'text' - free-form text of any length may be included in
# these latter fields provided the text block begins and ends with a semicolon
# as the first character of a new line. Note also that the query marks
# '?' are significant as placeholders, and should not be deleted where a data
# item is not given, UNLESS the accompanying data name is also deleted.
# Lines should not exceed 80 characters in length. The comments following
# a hash symbol '#' may be deleted if wished.

#=============================================================================
data_znvo
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef '- Form VI_vorinostat_31-10-2011.CIF'

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

loop_
_audit_conform_dict_name
_audit_conform_dict_version
_audit_conform_dict_location
cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic

# 1. SUBMISSION DETAILS

_publ_contact_author_name        'Dr Rafel Prohens'
_publ_contact_author_address     
;
Plataforma de Polimorfisme i Calorimetria
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
_publ_contact_author_email       rafel@ccit.ub.edu
_publ_contact_author_fax         '34 934037206'
_publ_contact_author_phone       '34 934034656'
_publ_requested_category         ?

_publ_contact_letter             
; Please consider this CIF submission for publication as a full paper in Acta
Cryst. Section C. The figures, Transfer of Copyright Agreement form and
powder profile will be sent on receipt of your acknowledgment letter.
;

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

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          
; ?
;
_journal_techeditor_code         ?
_journal_paper_category          ?
_iucr_compatibility_tag          ?
_journal_techeditor_notes        
; ?
;
_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

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

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Example CIF - Not for publication
;

# The loop structure below should contain the names and addresses of all
# authors, in the required order of publication. Repeat as necessary.

loop_
_publ_author_name
_publ_author_address
'Cristina Puigjaner'
; Plataforma de Polimorfisme i Calorimetria
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
'Rafael Barbas'
; Plataforma de Polimorfisme i Calorimetria
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
'Anna Portell'
; Plataforma de Polimorfisme i Calorimetria
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
'Ismael Valverde'
; Urquima SA
Uriach Group
08105 Barcelona
Spain
;
'Xavier Vila'
; Urquima SA
Uriach Group
08105 Barcelona
Spain
;
'Xavier Alcobe'
; Unitat de Difraccio de Raigs X
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
;
M.Font-Bardia
;
; Unitat de Difraccio de Raigs X
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;
'Rafel Prohens'
; Plataforma de Polimorfisme i Calorimetria
Centres Cientifics i Tecnologics
Universitat de Barcelona
08028 Barcelona
Spain
;

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

# 4. TEXT

_publ_section_synopsis           
; ?
;
_publ_section_abstract           
; ?
;
_publ_section_comment            
; ?
;
_publ_section_exptl_prep         
# Details of the preparation of the sample(s)
# should be given here.
; ?
;
_publ_section_exptl_refinement   
; ?
;
_publ_section_references         
; ?
;
_publ_section_figure_captions    
; ?
;
_publ_section_acknowledgements   
; ?
;

data_anom3b
_database_code_depnum_ccdc_archive 'CCDC 830150'
#TrackingRef '- Form I CCDC-830150.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N2 O3'
_chemical_formula_sum            'C14 H20 N2 O3'
_chemical_formula_weight         264.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   10.963(7)
_cell_length_b                   7.953(4)
_cell_length_c                   16.433(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.92(3)
_cell_angle_gamma                90.00
_cell_volume                     1419.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1083
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   Sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10527
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         30.93
_reflns_number_total             3677
_reflns_number_gt                3646
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MARXDS
_computing_cell_refinement       AUTOMAR
_computing_data_reduction        MARSCALE
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

_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 displacement parameters
of C5-C6 and C1-C6 lengths in the direction of the bond are restrained
to be equal within an effective standard deviation (DELU sentences)
;

_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^)+(0.0166P)^2^+0.2878P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3677
_refine_ls_number_parameters     172
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.489
_refine_ls_restrained_S_all      1.499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51762(10) 0.65527(17) 0.10956(7) 0.0672(3) Uani 1 1 d . . .
O2 O -0.29102(10) 0.25692(15) 0.16461(7) 0.0612(3) Uani 1 1 d . . .
O3 O -0.45254(10) 0.44659(16) 0.23873(7) 0.0684(3) Uani 1 1 d . . .
H3O H -0.4799 0.4575 0.1900 0.103 Uiso 1 1 calc R . .
N1 N 0.48965(11) 0.75861(17) -0.01932(7) 0.0537(3) Uani 1 1 d . . .
H1N H 0.4355 0.7726 -0.0619 0.064 Uiso 1 1 calc R . .
N2 N -0.32584(11) 0.46920(19) 0.24926(8) 0.0590(3) Uani 1 1 d . . .
H2N H -0.2937 0.5474 0.2815 0.071 Uiso 1 1 calc R . .
C1 C 0.69863(15) 0.8439(2) 0.03958(10) 0.0630(4) Uani 1 1 d U . .
H1 H 0.6830 0.8214 0.0927 0.076 Uiso 1 1 calc R . .
C2 C 0.81238(17) 0.9036(3) 0.02587(12) 0.0759(5) Uani 1 1 d . . .
H2A H 0.8728 0.9227 0.0705 0.091 Uiso 1 1 calc R . .
C3 C 0.83831(18) 0.9353(3) -0.05194(12) 0.0774(5) Uani 1 1 d . . .
H3A H 0.9158 0.9737 -0.0602 0.093 Uiso 1 1 calc R . .
C4 C 0.74848(17) 0.9097(3) -0.11711(12) 0.0720(5) Uani 1 1 d . . .
H4 H 0.7647 0.9324 -0.1701 0.086 Uiso 1 1 calc R . .
C5 C 0.63380(16) 0.8503(2) -0.10508(10) 0.0644(4) Uani 1 1 d U . .
H5 H 0.5738 0.8322 -0.1500 0.077 Uiso 1 1 calc R . .
C6 C 0.60799(13) 0.81789(19) -0.02690(9) 0.0486(3) Uani 1 1 d U . .
C7 C 0.44849(13) 0.6826(2) 0.04536(9) 0.0515(3) Uani 1 1 d . . .
C8 C 0.31637(13) 0.6330(2) 0.03226(9) 0.0553(4) Uani 1 1 d . . .
H8A H 0.3076 0.5327 -0.0016 0.066 Uiso 1 1 calc R . .
H8B H 0.2695 0.7219 0.0020 0.066 Uiso 1 1 calc R . .
C9 C 0.26111(14) 0.5990(2) 0.10995(9) 0.0577(4) Uani 1 1 d . . .
H9A H 0.3066 0.5089 0.1402 0.069 Uiso 1 1 calc R . .
H9B H 0.2693 0.6987 0.1442 0.069 Uiso 1 1 calc R . .
C10 C 0.12694(14) 0.5507(2) 0.09245(10) 0.0625(4) Uani 1 1 d . . .
H10A H 0.1191 0.4526 0.0570 0.075 Uiso 1 1 calc R . .
H10B H 0.0818 0.6419 0.0629 0.075 Uiso 1 1 calc R . .
C11 C 0.06859(14) 0.5121(2) 0.16882(9) 0.0601(4) Uani 1 1 d . . .
H11A H 0.1152 0.4231 0.1992 0.072 Uiso 1 1 calc R . .
H11B H 0.0744 0.6112 0.2035 0.072 Uiso 1 1 calc R . .
C12 C -0.06505(14) 0.4589(2) 0.15152(10) 0.0607(4) Uani 1 1 d . . .
H12A H -0.1125 0.5485 0.1223 0.073 Uiso 1 1 calc R . .
H12B H -0.0716 0.3605 0.1163 0.073 Uiso 1 1 calc R . .
C13 C -0.11921(13) 0.4187(2) 0.22906(9) 0.0564(4) Uani 1 1 d . . .
H13A H -0.0744 0.3254 0.2571 0.068 Uiso 1 1 calc R . .
H13B H -0.1096 0.5153 0.2654 0.068 Uiso 1 1 calc R . .
C14 C -0.25364(13) 0.3737(2) 0.21104(8) 0.0515(3) 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
O1 0.0597(7) 0.0805(9) 0.0589(6) 0.0058(6) -0.0009(5) -0.0059(6)
O2 0.0612(7) 0.0641(7) 0.0567(6) -0.0009(5) 0.0021(5) -0.0050(5)
O3 0.0550(6) 0.0797(9) 0.0700(7) 0.0060(6) 0.0067(5) -0.0038(6)
N1 0.0480(6) 0.0643(9) 0.0470(6) 0.0017(6) -0.0003(5) -0.0026(6)
N2 0.0501(7) 0.0657(9) 0.0598(7) 0.0009(6) 0.0030(6) -0.0038(6)
C1 0.0574(9) 0.0728(12) 0.0571(8) -0.0021(8) 0.0021(6) -0.0069(8)
C2 0.0654(11) 0.0901(15) 0.0699(11) -0.0027(10) 0.0006(8) -0.0101(10)
C3 0.0644(11) 0.0877(15) 0.0797(12) 0.0026(11) 0.0090(9) -0.0090(10)
C4 0.0667(11) 0.0814(13) 0.0682(11) 0.0068(9) 0.0100(8) -0.0065(9)
C5 0.0612(9) 0.0738(12) 0.0570(8) 0.0052(8) 0.0039(7) -0.0047(8)
C6 0.0455(7) 0.0485(8) 0.0514(7) -0.0005(6) 0.0049(5) -0.0006(6)
C7 0.0476(7) 0.0549(9) 0.0513(8) -0.0026(6) 0.0040(6) -0.0003(6)
C8 0.0496(8) 0.0637(10) 0.0515(8) 0.0013(7) 0.0029(6) -0.0023(7)
C9 0.0530(8) 0.0656(11) 0.0536(8) -0.0002(7) 0.0044(6) -0.0018(7)
C10 0.0560(9) 0.0741(12) 0.0569(9) 0.0019(8) 0.0057(7) -0.0023(8)
C11 0.0546(8) 0.0709(11) 0.0547(8) 0.0007(8) 0.0069(6) -0.0033(8)
C12 0.0538(8) 0.0712(11) 0.0561(8) 0.0016(8) 0.0039(7) -0.0041(8)
C13 0.0491(8) 0.0646(10) 0.0539(8) 0.0010(7) 0.0009(6) -0.0029(7)
C14 0.0509(8) 0.0578(9) 0.0450(7) 0.0037(6) 0.0037(6) -0.0028(7)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2306(18) . ?
O2 C14 1.2355(19) . ?
O3 N2 1.3876(18) . ?
O3 H3O 0.8200 . ?
N1 C7 1.3532(19) . ?
N1 C6 1.402(2) . ?
N1 H1N 0.8600 . ?
N2 C14 1.317(2) . ?
N2 H2N 0.8600 . ?
C1 C2 1.382(2) . ?
C1 C6 1.387(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.488(2) . ?
C8 C9 1.511(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.509(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.516(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.512(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.506(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O3 H3O 109.5 . . ?
C7 N1 C6 129.26(12) . . ?
C7 N1 H1N 115.4 . . ?
C6 N1 H1N 115.4 . . ?
C14 N2 O3 121.52(14) . . ?
C14 N2 H2N 119.2 . . ?
O3 N2 H2N 119.2 . . ?
C2 C1 C6 119.18(16) . . ?
C2 C1 H1 120.4 . . ?
C6 C1 H1 120.4 . . ?
C3 C2 C1 121.54(17) . . ?
C3 C2 H2A 119.2 . . ?
C1 C2 H2A 119.2 . . ?
C4 C3 C2 118.94(18) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 120.67(18) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.34(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.31(15) . . ?
C5 C6 N1 117.22(13) . . ?
C1 C6 N1 123.47(14) . . ?
O1 C7 N1 121.31(14) . . ?
O1 C7 C8 123.34(14) . . ?
N1 C7 C8 115.34(13) . . ?
C7 C8 C9 114.89(13) . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C8 112.23(13) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.90(13) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 114.14(13) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 112.53(13) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 111.83(12) . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 N2 123.92(15) . . ?
O2 C14 C13 122.16(15) . . ?
N2 C14 C13 113.92(14) . . ?

_diffrn_measured_fraction_theta_max 0.817
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.032

# Attachment '- Form III CCDC-830151.cif'

data_anom16a
_database_code_depnum_ccdc_archive 'CCDC 830151'
#TrackingRef '- Form III CCDC-830151.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 N2 O3'
_chemical_formula_sum            'C14 H20 N2 O3'
_chemical_formula_weight         264.32

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2

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'

_cell_length_a                   15.027(11)
_cell_length_b                   5.096(3)
_cell_length_c                   18.258(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.15(3)
_cell_angle_gamma                90.00
_cell_volume                     1355.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1027
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5776
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         32.21
_reflns_number_total             3257
_reflns_number_gt                2807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MARXDS
_computing_cell_refinement       AUTOMAR
_computing_data_reduction        MARSCALE
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

_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.
;

_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^)+(0.0979P)^2^+0.1528P] 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_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1541
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63410(13) 0.1173(3) 0.56466(10) 0.0505(4) Uani 1 1 d . . .
O2 O 0.64414(13) -0.1767(4) 0.04461(10) 0.0544(5) Uani 1 1 d . . .
O3 O 0.67880(14) 0.2290(4) -0.03760(10) 0.0581(5) Uani 1 1 d . . .
H3 H 0.7263 0.1427 -0.0275 0.087 Uiso 1 1 calc R . .
N1 N 0.63137(13) -0.3093(4) 0.59959(10) 0.0420(4) Uani 1 1 d . . .
H1 H 0.6282 -0.4674 0.5827 0.050 Uiso 1 1 calc R . .
N2 N 0.64623(14) 0.2569(4) 0.02681(10) 0.0436(4) Uani 1 1 d . . .
H2 H 0.6390 0.4107 0.0438 0.052 Uiso 1 1 calc R . .
C1 C 0.68217(15) -0.0814(5) 0.72187(12) 0.0437(5) Uani 1 1 d . . .
H1A H 0.7127 0.0439 0.7001 0.052 Uiso 1 1 calc R . .
C2 C 0.68553(15) -0.0697(4) 0.79791(12) 0.0436(5) Uani 1 1 d . . .
H2A H 0.7182 0.0642 0.8272 0.052 Uiso 1 1 calc R . .
C3 C 0.64052(16) -0.2561(5) 0.83103(13) 0.0451(5) Uani 1 1 d . . .
H3A H 0.6422 -0.2454 0.8822 0.054 Uiso 1 1 calc R . .
C4 C 0.59331(16) -0.4569(5) 0.78799(13) 0.0475(5) Uani 1 1 d . . .
H4 H 0.5639 -0.5835 0.8103 0.057 Uiso 1 1 calc R . .
C5 C 0.58957(15) -0.4708(5) 0.71083(12) 0.0442(5) Uani 1 1 d . . .
H5 H 0.5580 -0.6067 0.6816 0.053 Uiso 1 1 calc R . .
C6 C 0.63355(14) -0.2791(4) 0.67799(11) 0.0379(4) Uani 1 1 d . . .
C7 C 0.63371(15) -0.1160(4) 0.54917(11) 0.0394(4) Uani 1 1 d . . .
C8 C 0.64061(17) -0.2157(5) 0.47260(12) 0.0463(5) Uani 1 1 d . . .
H8A H 0.7041 -0.2611 0.4756 0.056 Uiso 1 1 calc R . .
H8B H 0.6047 -0.3754 0.4614 0.056 Uiso 1 1 calc R . .
C9 C 0.60875(16) -0.0271(5) 0.40782(12) 0.0430(5) Uani 1 1 d . . .
H9A H 0.6371 0.1427 0.4216 0.052 Uiso 1 1 calc R . .
H9B H 0.5428 -0.0050 0.3983 0.052 Uiso 1 1 calc R . .
C10 C 0.63282(15) -0.1236(5) 0.33595(12) 0.0409(4) Uani 1 1 d . . .
H10A H 0.6991 -0.1254 0.3443 0.049 Uiso 1 1 calc R . .
H10B H 0.6115 -0.3030 0.3265 0.049 Uiso 1 1 calc R . .
C11 C 0.59270(14) 0.0387(5) 0.26602(12) 0.0396(4) Uani 1 1 d . . .
H11A H 0.6095 0.2211 0.2764 0.047 Uiso 1 1 calc R . .
H11B H 0.5263 0.0271 0.2543 0.047 Uiso 1 1 calc R . .
C12 C 0.62598(16) -0.0518(5) 0.19776(12) 0.0429(5) Uani 1 1 d . . .
H12A H 0.6119 -0.2366 0.1890 0.052 Uiso 1 1 calc R . .
H12B H 0.6921 -0.0317 0.2085 0.052 Uiso 1 1 calc R . .
C13 C 0.58135(17) 0.1044(5) 0.12556(12) 0.0452(5) Uani 1 1 d . . .
H13A H 0.5167 0.0597 0.1096 0.054 Uiso 1 1 calc R . .
H13B H 0.5859 0.2906 0.1369 0.054 Uiso 1 1 calc R . .
C14 C 0.62649(15) 0.0479(5) 0.06168(12) 0.0423(4) 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
O1 0.0682(11) 0.0385(10) 0.0470(8) 0.0010(6) 0.0180(8) 0.0003(7)
O2 0.0707(12) 0.0424(10) 0.0539(10) 0.0004(7) 0.0226(8) 0.0019(7)
O3 0.0728(12) 0.0558(11) 0.0504(9) -0.0008(8) 0.0242(8) -0.0002(9)
N1 0.0539(10) 0.0322(10) 0.0411(9) -0.0023(6) 0.0137(7) -0.0007(7)
N2 0.0550(11) 0.0371(10) 0.0408(8) -0.0004(7) 0.0156(7) 0.0002(7)
C1 0.0493(11) 0.0389(12) 0.0437(10) 0.0012(8) 0.0128(9) -0.0042(9)
C2 0.0506(11) 0.0406(12) 0.0389(10) -0.0006(8) 0.0093(8) -0.0026(9)
C3 0.0518(12) 0.0419(12) 0.0414(10) 0.0009(9) 0.0110(8) 0.0014(9)
C4 0.0525(12) 0.0445(13) 0.0470(11) 0.0033(9) 0.0151(9) -0.0042(10)
C5 0.0529(11) 0.0364(12) 0.0441(10) -0.0013(8) 0.0134(9) -0.0049(9)
C6 0.0425(10) 0.0348(11) 0.0369(9) 0.0022(7) 0.0109(7) 0.0007(8)
C7 0.0465(10) 0.0340(12) 0.0382(9) -0.0019(8) 0.0113(8) 0.0029(8)
C8 0.0548(13) 0.0433(14) 0.0422(10) -0.0017(8) 0.0147(9) 0.0038(9)
C9 0.0467(11) 0.0423(12) 0.0411(10) -0.0007(8) 0.0130(8) 0.0035(8)
C10 0.0457(10) 0.0376(11) 0.0398(9) -0.0001(8) 0.0114(8) 0.0004(8)
C11 0.0447(10) 0.0353(11) 0.0403(9) -0.0006(7) 0.0134(8) 0.0018(8)
C12 0.0489(11) 0.0390(12) 0.0422(10) -0.0003(8) 0.0138(8) 0.0021(8)
C13 0.0545(12) 0.0392(12) 0.0443(10) 0.0028(8) 0.0169(9) 0.0035(8)
C14 0.0523(11) 0.0366(12) 0.0394(9) 0.0000(8) 0.0139(8) -0.0011(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.222(3) . ?
O2 C14 1.232(3) . ?
O3 N2 1.387(2) . ?
O3 H3 0.8200 . ?
N1 C7 1.355(3) . ?
N1 C6 1.432(3) . ?
N1 H1 0.8600 . ?
N2 C14 1.312(3) . ?
N2 H2 0.8600 . ?
C1 C2 1.378(3) . ?
C1 C6 1.380(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.515(3) . ?
C8 C9 1.508(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.526(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.517(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.523(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.545(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O3 H3 109.5 . . ?
C7 N1 C6 127.08(19) . . ?
C7 N1 H1 116.5 . . ?
C6 N1 H1 116.5 . . ?
C14 N2 O3 119.79(19) . . ?
C14 N2 H2 120.1 . . ?
O3 N2 H2 120.1 . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 H1A 120.0 . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C1 C6 C5 120.07(19) . . ?
C1 C6 N1 122.58(19) . . ?
C5 C6 N1 117.19(19) . . ?
O1 C7 N1 123.4(2) . . ?
O1 C7 C8 122.9(2) . . ?
N1 C7 C8 113.7(2) . . ?
C9 C8 C7 115.5(2) . . ?
C9 C8 H8A 108.4 . . ?
C7 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
C7 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 111.87(19) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 114.78(19) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 112.40(19) . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 112.41(19) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 112.1(2) . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 N2 122.9(2) . . ?
O2 C14 C13 122.4(2) . . ?
N2 C14 C13 114.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.750
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046

data_anoc11b
_database_code_depnum_ccdc_archive 'CCDC 830152'
#TrackingRef '- ammonia cocrystal CCDC 830152.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H20 N2 O3), H3 N '
_chemical_formula_sum            'C28 H43 N5 O6'
_chemical_formula_weight         545.67

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   71.963(14)
_cell_length_b                   4.995(2)
_cell_length_c                   8.096(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.19(8)
_cell_angle_gamma                90.00
_cell_volume                     2908(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12
_cell_measurement_theta_max      21

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'ENRAF-NONIUS, CAD4'
_diffrn_measurement_method       \w--2\q
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5222
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -106
_diffrn_reflns_limit_h_max       97
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         30.01
_reflns_number_total             4209
_reflns_number_gt                2437
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CAD-4/PC (Kretschmar, 1996)'
_computing_cell_refinement       'CAD-4/PC (Kretschmar, 1996)'
_computing_data_reduction        'XCAD4 (Harms and Wocadlo, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

_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.
;

_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^)+(0.1003P)^2^+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4209
_refine_ls_number_parameters     189
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.2590
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.2558
_refine_ls_wR_factor_gt          0.1866
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16278(4) 1.0674(6) 0.4431(4) 0.0576(10) Uani 1 1 d . . .
O2 O 0.03286(4) 0.5486(6) 0.5070(4) 0.0607(10) Uani 1 1 d . . .
O3 O 0.01278(4) 0.9815(6) 0.6093(4) 0.0636(10) Uani 1 1 d D . .
H3O H 0.00476(14) 0.854(2) 0.558(2) 0.076 Uiso 1 1 d D . .
N1 N 0.17497(5) 0.6505(6) 0.4323(4) 0.0402(9) Uani 1 1 d . . .
H1N H 0.1721 0.4836 0.4368 0.048 Uiso 1 1 calc R . .
N2 N 0.02895(5) 0.9940(6) 0.5243(4) 0.0420(9) Uani 1 1 d D . .
H2N H 0.0330 1.1491 0.4969 0.050 Uiso 1 1 calc R . .
C1 C 0.19827(6) 0.9194(8) 0.2930(5) 0.0412(11) Uani 1 1 d . . .
H1 H 0.1892 1.0357 0.2501 0.049 Uiso 1 1 calc R . .
C2 C 0.21695(6) 0.9545(9) 0.2576(6) 0.0504(12) Uani 1 1 d . . .
H2 H 0.2202 1.0959 0.1899 0.060 Uiso 1 1 calc R . .
C3 C 0.23086(7) 0.7833(9) 0.3210(6) 0.0497(12) Uani 1 1 d . . .
H3 H 0.2433 0.8124 0.3002 0.060 Uiso 1 1 calc R . .
C4 C 0.22541(6) 0.5712(9) 0.4146(6) 0.0507(13) Uani 1 1 d . . .
H4 H 0.2344 0.4502 0.4540 0.061 Uiso 1 1 calc R . .
C5 C 0.20739(6) 0.5318(8) 0.4519(6) 0.0449(11) Uani 1 1 d . . .
H5 H 0.2043 0.3864 0.5170 0.054 Uiso 1 1 calc R . .
C6 C 0.19351(6) 0.7067(7) 0.3937(5) 0.0356(10) Uani 1 1 d . . .
C7 C 0.16095(6) 0.8249(9) 0.4635(5) 0.0426(11) Uani 1 1 d . . .
C8 C 0.14359(6) 0.7042(8) 0.5218(6) 0.0485(12) Uani 1 1 d . . .
H8A H 0.1441 0.5119 0.5058 0.058 Uiso 1 1 calc R . .
H8B H 0.1428 0.7376 0.6394 0.058 Uiso 1 1 calc R . .
C9 C 0.12675(6) 0.8092(9) 0.4360(6) 0.0531(13) Uani 1 1 d . . .
H9A H 0.1272 0.7641 0.3197 0.064 Uiso 1 1 calc R . .
H9B H 0.1268 1.0029 0.4448 0.064 Uiso 1 1 calc R . .
C10 C 0.10842(6) 0.7036(9) 0.5022(6) 0.0502(12) Uani 1 1 d . . .
H1OA H 0.1085 0.5097 0.4956 0.060 Uiso 1 1 calc R . .
H10B H 0.1079 0.7519 0.6180 0.060 Uiso 1 1 calc R . .
C11 C 0.09113(6) 0.8072(10) 0.4118(6) 0.0571(13) Uani 1 1 d . . .
H11A H 0.0911 0.7441 0.2985 0.069 Uiso 1 1 calc R . .
H11B H 0.0917 1.0012 0.4090 0.069 Uiso 1 1 calc R . .
C12 C 0.07300(6) 0.7259(9) 0.4856(6) 0.0474(12) Uani 1 1 d . . .
H12A H 0.0722 0.5320 0.4849 0.057 Uiso 1 1 calc R . .
H12B H 0.0731 0.7840 0.5999 0.057 Uiso 1 1 calc R . .
C13 C 0.05599(6) 0.8376(9) 0.3976(5) 0.0419(11) Uani 1 1 d . . .
H13A H 0.0574 1.0299 0.3873 0.050 Uiso 1 1 calc R . .
H13B H 0.0550 0.7631 0.2869 0.050 Uiso 1 1 calc R . .
C14 C 0.03857(6) 0.7804(8) 0.4824(5) 0.0390(11) Uani 1 1 d . . .
N3 N 0.0000 0.5097(9) 0.2500 0.0414(13) Uani 1 2 d SD . .
H3AN H -0.0045(6) 0.662(6) 0.205(7) 0.050 Uiso 0.50 1 d PD . .
H3BN H -0.0087(5) 0.382(7) 0.235(7) 0.050 Uiso 0.50 1 d PD . .
H3CN H 0.0098(5) 0.461(9) 0.191(7) 0.050 Uiso 0.50 1 d PD . .

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
O1 0.056(2) 0.0446(19) 0.072(3) -0.0026(18) -0.0003(17) 0.0007(17)
O2 0.060(2) 0.050(2) 0.073(3) -0.0001(19) 0.0081(18) -0.0015(17)
O3 0.060(2) 0.057(2) 0.075(3) -0.0023(19) 0.0238(19) -0.0085(18)
N1 0.039(2) 0.034(2) 0.048(2) -0.0009(17) 0.0027(18) -0.0041(16)
N2 0.041(2) 0.033(2) 0.052(2) 0.0022(18) 0.0070(18) -0.0052(17)
C1 0.043(3) 0.038(2) 0.043(3) -0.002(2) 0.004(2) -0.001(2)
C2 0.051(3) 0.045(3) 0.055(3) -0.001(2) 0.005(2) -0.007(2)
C3 0.046(3) 0.050(3) 0.054(3) -0.003(3) 0.005(2) 0.000(2)
C4 0.049(3) 0.045(3) 0.058(3) -0.001(2) 0.006(2) 0.004(2)
C5 0.046(3) 0.039(2) 0.050(3) 0.001(2) 0.003(2) 0.000(2)
C6 0.036(3) 0.031(2) 0.039(3) -0.001(2) 0.004(2) -0.002(2)
C7 0.044(3) 0.036(2) 0.047(3) -0.002(2) 0.002(2) 0.000(2)
C8 0.044(3) 0.046(3) 0.055(3) -0.002(2) -0.001(2) 0.000(2)
C9 0.050(3) 0.053(3) 0.057(3) 0.002(3) 0.001(3) -0.001(2)
C10 0.047(3) 0.057(3) 0.047(3) -0.005(3) 0.004(2) 0.000(2)
C11 0.047(3) 0.059(3) 0.066(3) 0.002(3) 0.004(3) 0.003(3)
C12 0.039(3) 0.051(3) 0.053(3) 0.003(2) 0.004(2) -0.001(2)
C13 0.043(3) 0.053(3) 0.029(2) -0.001(2) 0.000(2) 0.002(2)
C14 0.036(3) 0.040(3) 0.041(3) -0.006(2) 0.001(2) 0.001(2)
N3 0.051(3) 0.039(3) 0.034(3) 0.000 -0.005(3) 0.000

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.230(5) . ?
O2 C14 1.247(5) . ?
O3 N2 1.376(4) . ?
O3 H3O 0.945(15) . ?
N1 C7 1.364(5) . ?
N1 C6 1.410(5) . ?
N1 H1N 0.8600 . ?
N2 C14 1.323(5) . ?
N2 H2N 0.8600 . ?
C1 C6 1.390(5) . ?
C1 C2 1.396(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C7 C8 1.481(6) . ?
C8 C9 1.470(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.536(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.511(7) . ?
C10 H1OA 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.511(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.500(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.480(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N3 H3AN 0.9000(12) . ?
N3 H3BN 0.8999(11) . ?
N3 H3CN 0.9000(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O3 H3O 108.9(13) . . ?
C7 N1 C6 128.8(3) . . ?
C7 N1 H1N 115.6 . . ?
C6 N1 H1N 115.6 . . ?
C14 N2 O3 123.5(3) . . ?
C14 N2 H2N 118.2 . . ?
O3 N2 H2N 118.2 . . ?
C6 C1 C2 118.5(4) . . ?
C6 C1 H1 120.8 . . ?
C2 C1 H1 120.8 . . ?
C1 C2 C3 121.9(4) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 117.4(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 122.1(5) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.1(4) . . ?
C1 C6 N1 122.6(4) . . ?
C5 C6 N1 118.2(4) . . ?
O1 C7 N1 121.3(4) . . ?
O1 C7 C8 122.7(4) . . ?
N1 C7 C8 116.0(4) . . ?
C9 C8 C7 113.2(4) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 114.6(4) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 114.6(4) . . ?
C11 C10 H1OA 108.6 . . ?
C9 C10 H1OA 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H1OA C10 H10B 107.6 . . ?
C10 C11 C12 115.1(4) . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C12 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
C13 C12 C11 114.4(4) . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C12 113.5(4) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
O2 C14 N2 121.9(4) . . ?
O2 C14 C13 122.9(4) . . ?
N2 C14 C13 115.1(4) . . ?
H3AN N3 H3BN 107.8(11) . . ?
H3AN N3 H3CN 106.9(11) . . ?
H3BN N3 H3CN 107.4(11) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.125

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

#=============================================================================
# If more than one structure is reported, the remaining sections should be
# completed per structure. For each data set, replace the '?' in the
# data_? line below by a unique identifier.

data_a-voronistat2
_database_code_depnum_ccdc_archive 'CCDC 830811'
#TrackingRef '- Form VI_vorinostat_31-10-2011.CIF'

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
suberoylanilide hydroxamic acid
;
_chemical_name_common            'suberoylanilide hydroxamic acid'
_chemical_formula_moiety         'C14 H20 N2 O3'
_chemical_formula_structural     'C14 H20 N2 O3'
_chemical_formula_analytical     ?
_chemical_formula_iupac          'C14 H20 N2 O3'
_chemical_formula_sum            'C14 H20 N2 O3'
_chemical_formula_weight         264.32
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
o 3.04850 13.27710 2.28680 5.70110 1.54630 0.32390 0.86700 32.90890 0.25080
0.04700 0.03200
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
h 0.49300 10.51090 0.32291 26.12570 0.14019 3.14236 0.04081 57.79970 0.00304
0.00000 0.00000
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
n 12.21260 0.00570 3.13220 9.89330 2.01250 28.99750 1.16630 0.58260 -11.52900
0.02900 0.01800
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5
c 2.31000 20.84390 1.02000 10.20750 1.58860 0.56870 0.86500 51.65120 0.21560
0.01700 0.00900
International_Tables_for_Crystallography_Vol.C(1991)_Tables_6.1.1.4_and_6.1.1.5

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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz #<--must include 'x,y,z'
x,y,z
-x+1/2,y+1/2,-z+1/2
-x,-y,-z
x+1/2,-y+1/2,z+1/2

_cell_length_a                   19.3146(4)
_cell_length_b                   8.46572(7)
_cell_length_c                   8.94208(10)
_cell_angle_alpha                90.00000
_cell_angle_beta                 94.5220(12)
_cell_angle_gamma                90.00000
_cell_volume                     1457.59(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_special_details            
; ?
;
# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              ? # perpendicular to
# equatorial plane
_pd_spec_size_equat              ? # parallel to
# scattering vector
# in transmission
_pd_spec_size_thick              ? # parallel to
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode              ? # options are 'reflection'
# or 'transmission'
_pd_spec_shape                   ? # options are 'cylinder'
# 'flat_sheet' or 'irregular'
_pd_char_particle_morphology     ?
_pd_char_colour                  white

# The following three fields describe the preparation of the specimen.
# The cooling rate is in K/min. The pressure at which the sample was
# prepared is in kPa. The temperature of preparation is in K.

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             ?

_exptl_crystal_density_diffrn    1.20432

# The next four fields are normally only needed for transmission experiments.

_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record
# the powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; ?
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      295
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source_target            'Cu '

_diffrn_radiation_monochromator  'elliptic x-ray mirror'
_diffrn_measurement_device_type  "PANalytical X'Pert PRO MPD"
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ? # Not in version 2.0.1
_diffrn_detector                 ?
_diffrn_detector_type            ? # make or model of detector
_pd_meas_scan_method             ? # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;

# The following four items give details of the measured (not processed)
# powder pattern. Angles are in degrees.

_pd_meas_number_of_points        4845
_pd_meas_2theta_range_min        7.01200
_pd_meas_2theta_range_max        69.98400
_pd_meas_2theta_range_inc        0.013003

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

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_proc_ls_profile_function     ?
_pd_proc_ls_background_function  ?
_pd_proc_ls_pref_orient_corr     
; ?
;

# The following profile R-factors are NOT CORRECTED for background
# The sum is extended to all non-excluded points.
# These are the current CIF standard

_pd_proc_ls_prof_R_factor        3.1669
_pd_proc_ls_prof_wR_factor       4.6144
_pd_proc_ls_prof_wR_expected     1.1415

# The following profile R-factors are CORRECTED for background
# The sum is extended to all non-excluded points.
# These items are not in the current CIF standard, but are defined above

_pd_proc_ls_prof_cR_factor       8.0295
_pd_proc_ls_prof_cwR_factor      8.6928
_pd_proc_ls_prof_cwR_expected    2.1504

# The following items are not in the CIF standard, but are defined above

_pd_proc_ls_prof_chi2            16.3411
_pd_proc_ls_prof_echi2           16.7342

# Items related to LS refinement

_refine_ls_shift/su_max          0.1
_refine_ls_R_I_factor            2.8322
_refine_ls_number_reflns         1586
_refine_ls_number_parameters     134
_refine_ls_number_restraints     106
_refine_ls_hydrogen_treatment    refU

# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the
# intensities used in the refinement.

_pd_proc_2theta_range_min        7.0095
_pd_proc_2theta_range_max        69.9815
_pd_proc_2theta_range_inc        0.013003
_pd_proc_wavelength              1.540600

_pd_block_diffractogram_id       ? # The id used for the block containing
# the powder pattern profile (section 11)

# Give appropriate details in the next two text fields.

_pd_proc_info_excluded_regions   ?
_pd_proc_info_data_reduction     ?

# The following items are used to identify the programs used.

_computing_data_collection       ?
_computing_structure_solution    ?
_computing_structure_refinement  FULLPROF
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type # Not in version 2.0.1
_atom_site_type_symbol
O1 0.2900(4) 0.7060(10) 0.3945(7) 0.047(3) 1.00000 Uiso O
O2 0.7470(4) 0.4408(8) 0.1398(8) 0.047(3) 1.00000 Uiso O
O3 0.8518(3) 0.6456(9) 0.1481(7) 0.047(3) 1.00000 Uiso O
H4 0.84130 0.67156 0.05303 0.34(2) 1.00000 Uiso H
N5 0.22796(15) 0.6124(12) 0.1874(6) 0.049(5) 1.00000 Uiso N
H6 0.23300 0.62104 0.09487 0.34(2) 1.00000 Uiso H
N7 0.7924(4) 0.6624(11) 0.2294(11) 0.049(5) 1.00000 Uiso N
H8 0.78011 0.73984 0.27725 0.34(2) 1.00000 Uiso H
C9 0.14834(12) 0.6152(12) 0.38348(18) 0.065(2) 1.00000 Uiso C
H10 0.18432 0.63752 0.45717 0.34(2) 1.00000 Uiso H
C11 0.08039(8) 0.6056(13) 0.42207(20) 0.065(2) 1.00000 Uiso C
H12 0.07207 0.60598 0.52358 0.34(2) 1.00000 Uiso H
C13 0.02489(9) 0.6265(13) 0.31495(19) 0.065(2) 1.00000 Uiso C
H14 -0.01967 0.61927 0.34625 0.34(2) 1.00000 Uiso H
C15 0.03698(12) 0.6201(13) 0.1654(2) 0.065(2) 1.00000 Uiso C
H16 -0.00047 0.59602 0.09723 0.34(2) 1.00000 Uiso H
C17 0.10466(8) 0.6290(10) 0.1205(2) 0.065(2) 1.00000 Uiso C
H18 0.11432 0.59664 0.02461 0.34(2) 1.00000 Uiso H
C19 0.15903(9) 0.6295(14) 0.23292(18) 0.065(2) 1.00000 Uiso C
C20 0.2878(4) 0.6593(18) 0.2651(10) 0.065(2) 1.00000 Uiso C
C21 0.3560(3) 0.6116(9) 0.2034(8) 0.065(2) 1.00000 Uiso C
H22 0.35091 0.66556 0.10626 0.34(2) 1.00000 Uiso H
H23 0.35323 0.49877 0.18620 0.34(2) 1.00000 Uiso H
C24 0.4217(4) 0.6585(8) 0.2834(8) 0.065(2) 1.00000 Uiso C
H25 0.42120 0.61729 0.38671 0.34(2) 1.00000 Uiso H
H26 0.42441 0.77319 0.29105 0.34(2) 1.00000 Uiso H
C27 0.4793(3) 0.5895(8) 0.2001(8) 0.065(2) 1.00000 Uiso C
H28 0.46916 0.48228 0.17894 0.34(2) 1.00000 Uiso H
H29 0.48628 0.65366 0.11724 0.34(2) 1.00000 Uiso H
C30 0.5461(3) 0.5966(9) 0.2960(7) 0.065(2) 1.00000 Uiso C
H31 0.55417 0.68556 0.36682 0.34(2) 1.00000 Uiso H
H32 0.54880 0.50258 0.37429 0.34(2) 1.00000 Uiso H
C33 0.6101(3) 0.5746(8) 0.2110(8) 0.065(2) 1.00000 Uiso C
H34 0.61041 0.66552 0.14562 0.34(2) 1.00000 Uiso H
H35 0.60649 0.48162 0.14954 0.34(2) 1.00000 Uiso H
C36 0.6798(4) 0.5725(9) 0.3070(8) 0.065(2) 1.00000 Uiso C
H37 0.68663 0.66411 0.36470 0.34(2) 1.00000 Uiso H
H38 0.67926 0.48311 0.37535 0.34(2) 1.00000 Uiso H
C39 0.7406(5) 0.5651(12) 0.2085(16) 0.065(2) 1.00000 Uiso C

# Note: if the displacement parameters were refined anisotropically
# the U matrices should be given as for single-crystal studies.

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

# 10. MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.220(12) . ?
O2 C39 1.230(13) . ?
O3 H4 0.886 . ?
O3 N7 1.413(11) . ?
H4 O3 0.886 . ?
N5 H6 0.844 . ?
N5 C19 1.430(4) . ?
N5 C20 1.360(10) . ?
H6 N5 0.844 . ?
N7 O3 1.413(11) . ?
N7 H8 0.828 . ?
N7 C39 1.298(13) . ?
H8 N7 0.828 . ?
C9 H10 0.938 . ?
C9 C11 1.385(3) . ?
C9 C19 1.383(3) . ?
H10 C9 0.938 . ?
C11 C9 1.385(3) . ?
C11 H12 0.9342 . ?
C11 C13 1.391(3) . ?
H12 C11 0.9342 . ?
C13 C11 1.391(3) . ?
C13 H14 0.9278 . ?
C13 C15 1.377(3) . ?
H14 C13 0.9278 . ?
C15 C13 1.377(3) . ?
C15 H16 0.931 . ?
C15 C17 1.399(3) . ?
H16 C15 0.931 . ?
C17 C15 1.399(3) . ?
C17 H18 0.933 . ?
C17 C19 1.395(2) . ?
H18 C17 0.933 . ?
C19 N5 1.430(4) . ?
C19 C9 1.383(3) . ?
C19 C17 1.395(2) . ?
C20 O1 1.220(12) . ?
C20 N5 1.360(10) . ?
C20 C21 1.522(11) . ?
C21 C20 1.522(11) . ?
C21 H22 0.979 . ?
C21 H23 0.968 . ?
C21 C24 1.462(9) . ?
H22 C21 0.979 . ?
H23 C21 0.968 . ?
C24 C21 1.462(9) . ?
C24 H25 0.988 . ?
C24 H26 0.974 . ?
C24 C27 1.505(10) . ?
H25 C24 0.988 . ?
H26 C24 0.974 . ?
C27 C24 1.505(10) . ?
C27 H28 0.945 . ?
C27 H29 0.937 . ?
C27 C30 1.493(8) . ?
H28 C27 0.945 . ?
H29 C27 0.937 . ?
C30 C27 1.494(8) . ?
C30 H31 0.988 . ?
C30 H32 1.058 . ?
C30 C33 1.513(9) . ?
H31 C30 0.988 . ?
H32 C30 1.058 . ?
C33 C30 1.513(9) . ?
C33 H34 0.967 . ?
C33 H35 0.959 . ?
C33 C36 1.539(9) . ?
H34 C33 0.967 . ?
H35 C33 0.959 . ?
C36 C33 1.539(10) . ?
C36 H37 0.935 . ?
C36 H38 0.973 . ?
C36 C39 1.524(14) . ?
H37 C36 0.935 . ?
H38 C36 0.973 . ?
C39 O2 1.230(13) . ?
C39 N7 1.298(13) . ?
C39 C36 1.524(14) . ?

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
H4 O3 N7 109.6 . . ?
H6 N5 C19 116.9 . . ?
H6 N5 C20 108.5 . . ?
C19 N5 C20 126.7(7) . . ?
O3 N7 H8 128.6 . . ?
O3 N7 C39 120.7(11) . . ?
H8 N7 C39 109.1 . . ?
H10 C9 C11 120.0 . . ?
H10 C9 C19 120.4 . . ?
C11 C9 C19 117.7(3) . . ?
C9 C11 H12 118.7 . . ?
C9 C11 C13 121.0(3) . . ?
H12 C11 C13 119.1 . . ?
C11 C13 H14 117.8 . . ?
C11 C13 C15 118.9(2) . . ?
H14 C13 C15 121.5 . . ?
C13 C15 H16 117.5 . . ?
C13 C15 C17 120.7(2) . . ?
H16 C15 C17 121.3 . . ?
C15 C17 H18 120.5 . . ?
C15 C17 C19 117.4(3) . . ?
H18 C17 C19 118.0 . . ?
N5 C19 C9 118.8(4) . . ?
N5 C19 C17 117.3(3) . . ?
C9 C19 C17 122.6(2) . . ?
O1 C20 N5 122.9(10) . . ?
H22 C21 H23 108.6 . . ?
H22 C21 C24 109.3 . . ?
H23 C21 C24 112.4 . . ?
C21 C24 H25 106.8 . . ?
C21 C24 H26 110.2 . . ?
H25 C24 H26 106.9 . . ?
H28 C27 H29 116.0 . . ?
H28 C27 C30 108.1 . . ?
H29 C27 C30 105.0 . . ?
C27 C30 H31 119.0 . . ?
C27 C30 H32 110.2 . . ?
H31 C30 H32 98.8 . . ?
H34 C33 H35 108.1 . . ?
H37 C36 H38 107.8 . . ?
O2 C39 N7 120.5(12) . . ?