# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
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data_compound_3
_database_code_depnum_ccdc_archive 'CCDC 870274'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C31 H35 N3 O9), C4 H8 O'
_chemical_formula_sum            'C66 H78 N6 O19'
_chemical_formula_weight         1259.34

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0564(5)
_cell_length_b                   14.5528(8)
_cell_length_c                   15.2944(8)
_cell_angle_alpha                61.687(2)
_cell_angle_beta                 87.605(2)
_cell_angle_gamma                88.859(2)
_cell_volume                     1577.27(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4195
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      26.70

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3664
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   
;
See Sheldrick, G. M. (2002). SADABS.
University of Gottingen, Germany.
;

_exptl_special_details           
;
The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_monochromator  
;
graphite model mounted in "parallel" mode
;
_diffrn_measurement_device_type  
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_detector       'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean 
;
120 microns
;
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19853
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_sigmaI/netI    0.1033
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7085
_reflns_number_gt                4178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_cell_refinement       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction        
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;

_refine_special_details          
;

Measurements were carried out at 150 K on a Bruker-Nonius Apex X8
diffractometer equipped with an Apex II CCD detector and using
graphite monochromated Mo-Kalpha radiation from a FR591 rotating anode
generator. The structure was solved by direct methods and refined
using SHELXL-97. The compound crystallises in the triclinic space
group P-1 with two molecules of C31 H35 N3 O9 and one molecule of THF
in the unit cell. The THF molecule is disordered on the
inversion centre.

All non-hydrogen atoms were refined anisotropically.
All H atoms bonded to carbon and nitrogen were placed in calculated
positions and refined using a riding model.

C-H distances: CH3, 0.98\A; CH2, 0.99\A; CH, 1.00\A; aromatic, 0.95\A.

N-H distances: 0.88\A.

All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl
and hydroxyl) Ueq of the parent atom.

C.Kilner 8 April 2012



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^)+(0.0486P)^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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7085
_refine_ls_number_parameters     440
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_restrained_S_all      0.974
_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
C1 C 0.6415(2) 0.09478(16) 0.57406(14) 0.0221(5) Uani 1 1 d . . .
C2 C 0.5739(2) 0.17444(16) 0.59069(14) 0.0209(4) Uani 1 1 d . . .
C3 C 0.5113(2) 0.26180(16) 0.50917(14) 0.0218(4) Uani 1 1 d . . .
H3 H 0.4646 0.3177 0.5175 0.026 Uiso 1 1 calc R . .
C4 C 0.5170(2) 0.26742(16) 0.41528(14) 0.0212(4) Uani 1 1 d . . .
C5 C 0.5879(2) 0.18735(16) 0.40131(14) 0.0236(5) Uani 1 1 d . . .
H5 H 0.5951 0.1929 0.3368 0.028 Uiso 1 1 calc R . .
C6 C 0.6484(3) 0.09901(17) 0.48204(15) 0.0263(5) Uani 1 1 d . . .
H6 H 0.6935 0.0426 0.4739 0.032 Uiso 1 1 calc R . .
O7 O 0.6464(2) -0.08335(12) 0.67865(11) 0.0362(4) Uani 1 1 d . . .
N7 N 0.7081(2) 0.00113(14) 0.65877(12) 0.0255(4) Uani 1 1 d . . .
O8 O 0.8221(2) 0.01239(13) 0.70301(12) 0.0410(4) Uani 1 1 d . . .
O9 O 0.56721(17) 0.15524(11) 0.68691(9) 0.0260(3) Uani 1 1 d . . .
C10 C 0.5199(3) 0.23829(17) 0.70998(15) 0.0286(5) Uani 1 1 d . . .
H10 H 0.4175 0.2738 0.6742 0.034 Uiso 1 1 calc R . .
C11 C 0.4828(3) 0.1836(2) 0.82096(16) 0.0427(7) Uani 1 1 d . . .
H11A H 0.3929 0.1331 0.8370 0.064 Uiso 1 1 calc R . .
H11B H 0.4488 0.2353 0.8422 0.064 Uiso 1 1 calc R . .
H11C H 0.5826 0.1472 0.8556 0.064 Uiso 1 1 calc R . .
C12 C 0.6587(4) 0.3160(2) 0.67980(19) 0.0520(7) Uani 1 1 d . . .
H12A H 0.7566 0.2817 0.7181 0.078 Uiso 1 1 calc R . .
H12B H 0.6239 0.3734 0.6928 0.078 Uiso 1 1 calc R . .
H12C H 0.6861 0.3436 0.6088 0.078 Uiso 1 1 calc R . .
O13 O 0.4238(2) 0.44411(12) 0.33852(10) 0.0339(4) Uani 1 1 d . . .
C13 C 0.4440(2) 0.36357(16) 0.33228(14) 0.0232(5) Uani 1 1 d . . .
N14 N 0.4017(2) 0.35386(13) 0.25175(11) 0.0225(4) Uani 1 1 d . . .
H14 H 0.4147 0.2914 0.2568 0.027 Uiso 1 1 calc R . .
C15 C 0.3397(2) 0.43134(15) 0.16133(14) 0.0205(4) Uani 1 1 d . . .
C16 C 0.2910(2) 0.53064(16) 0.14405(14) 0.0239(5) Uani 1 1 d . . .
H16 H 0.2964 0.5497 0.1953 0.029 Uiso 1 1 calc R . .
C17 C 0.2341(3) 0.60215(16) 0.05095(15) 0.0254(5) Uani 1 1 d . . .
H17 H 0.2021 0.6701 0.0392 0.030 Uiso 1 1 calc R . .
C18 C 0.2236(2) 0.57579(16) -0.02454(14) 0.0214(5) Uani 1 1 d . . .
C19 C 0.2718(2) 0.47547(16) -0.00694(14) 0.0219(5) Uani 1 1 d . . .
H19 H 0.2653 0.4568 -0.0584 0.026 Uiso 1 1 calc R . .
C20 C 0.3289(2) 0.40319(15) 0.08495(14) 0.0207(4) Uani 1 1 d . . .
O21 O 0.38178(18) 0.30402(11) 0.11044(9) 0.0259(3) Uani 1 1 d . . .
C22 C 0.3684(3) 0.26246(16) 0.04081(14) 0.0251(5) Uani 1 1 d . . .
H22 H 0.4100 0.3155 -0.0267 0.030 Uiso 1 1 calc R . .
C23 C 0.1892(3) 0.23594(18) 0.03586(16) 0.0322(5) Uani 1 1 d . . .
H23A H 0.1475 0.1854 0.1024 0.048 Uiso 1 1 calc R . .
H23B H 0.1826 0.2057 -0.0091 0.048 Uiso 1 1 calc R . .
H23C H 0.1217 0.2995 0.0111 0.048 Uiso 1 1 calc R . .
C24 C 0.4810(3) 0.16731(17) 0.07947(15) 0.0301(5) Uani 1 1 d . . .
H24A H 0.5928 0.1872 0.0872 0.045 Uiso 1 1 calc R . .
H24B H 0.4862 0.1396 0.0322 0.045 Uiso 1 1 calc R . .
H24C H 0.4366 0.1138 0.1440 0.045 Uiso 1 1 calc R . .
O25 O 0.17318(19) 0.75104(11) -0.14683(10) 0.0330(4) Uani 1 1 d . . .
C25 C 0.1646(2) 0.65802(16) -0.12271(14) 0.0221(5) Uani 1 1 d . . .
N26 N 0.0996(2) 0.62253(13) -0.18177(11) 0.0225(4) Uani 1 1 d . . .
H26 H 0.0935 0.5543 -0.1565 0.027 Uiso 1 1 calc R . .
C27 C 0.0405(2) 0.68178(16) -0.27902(14) 0.0207(4) Uani 1 1 d . . .
C28 C -0.0061(2) 0.78608(16) -0.32008(14) 0.0224(5) Uani 1 1 d . . .
H28 H -0.0001 0.8224 -0.2825 0.027 Uiso 1 1 calc R . .
C29 C -0.0616(2) 0.83682(16) -0.41663(14) 0.0227(5) Uani 1 1 d . . .
H29 H -0.0918 0.9084 -0.4453 0.027 Uiso 1 1 calc R . .
C30 C -0.0733(2) 0.78436(16) -0.47160(14) 0.0208(4) Uani 1 1 d . . .
C31 C -0.0304(2) 0.67890(16) -0.42964(14) 0.0232(5) Uani 1 1 d . . .
H31 H -0.0410 0.6424 -0.4667 0.028 Uiso 1 1 calc R . .
C32 C 0.0276(2) 0.62728(15) -0.33403(14) 0.0214(4) Uani 1 1 d . . .
O33 O 0.07468(18) 0.52502(11) -0.28390(10) 0.0283(4) Uani 1 1 d . . .
C34 C 0.0643(3) 0.45763(16) -0.32931(15) 0.0267(5) Uani 1 1 d . . .
H34 H -0.0456 0.4672 -0.3606 0.032 Uiso 1 1 calc R . .
C35 C 0.2031(3) 0.48102(18) -0.40676(16) 0.0345(6) Uani 1 1 d . . .
H35A H 0.1903 0.5522 -0.4611 0.052 Uiso 1 1 calc R . .
H35B H 0.1984 0.4314 -0.4330 0.052 Uiso 1 1 calc R . .
H35C H 0.3104 0.4746 -0.3764 0.052 Uiso 1 1 calc R . .
C36 C 0.0767(3) 0.34812(17) -0.24366(16) 0.0334(5) Uani 1 1 d . . .
H36A H 0.1821 0.3402 -0.2110 0.050 Uiso 1 1 calc R . .
H36B H 0.0719 0.2976 -0.2688 0.050 Uiso 1 1 calc R . .
H36C H -0.0159 0.3356 -0.1957 0.050 Uiso 1 1 calc R . .
O37 O -0.13509(18) 0.79486(11) -0.62830(10) 0.0284(4) Uani 1 1 d . . .
C37 C -0.1302(2) 0.83638(16) -0.57592(14) 0.0217(5) Uani 1 1 d . . .
O38 O -0.17615(17) 0.93636(11) -0.60612(9) 0.0256(3) Uani 1 1 d . . .
C38 C -0.2226(3) 0.99507(17) -0.70921(14) 0.0282(5) Uani 1 1 d . . .
H38A H -0.1261 1.0015 -0.7530 0.042 Uiso 1 1 calc R . .
H38B H -0.2607 1.0648 -0.7227 0.042 Uiso 1 1 calc R . .
H38C H -0.3121 0.9585 -0.7215 0.042 Uiso 1 1 calc R . .
O51 O 0.0960(5) 0.8729(3) 0.0680(2) 0.0477(9) Uani 0.50 1 d PDU A -1
C52 C 0.1275(8) 0.9403(4) -0.0359(4) 0.0408(15) Uani 0.50 1 d PDU A -1
H52A H 0.1178 0.9013 -0.0737 0.049 Uiso 0.50 1 calc PR A -1
H52B H 0.2408 0.9701 -0.0479 0.049 Uiso 0.50 1 calc PR A -1
C53 C -0.0039(10) 1.0276(6) -0.0679(5) 0.0472(19) Uani 0.50 1 d PDU A -1
H53A H 0.0481 1.0970 -0.1079 0.057 Uiso 0.50 1 calc PR A -1
H53B H -0.0895 1.0179 -0.1075 0.057 Uiso 0.50 1 calc PR A -1
C54 C -0.0800(9) 1.0164(6) 0.0306(5) 0.0504(17) Uani 0.50 1 d PDU A -1
H54A H -0.1942 0.9880 0.0429 0.060 Uiso 0.50 1 calc PR A -1
H54B H -0.0825 1.0844 0.0308 0.060 Uiso 0.50 1 calc PR A -1
C55 C 0.0386(12) 0.9392(6) 0.1086(5) 0.054(2) Uani 0.50 1 d PDU A -1
H55A H 0.1325 0.9766 0.1174 0.065 Uiso 0.50 1 calc PR A -1
H55B H -0.0208 0.8984 0.1735 0.065 Uiso 0.50 1 calc PR A -1

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
C1 0.0215(11) 0.0226(12) 0.0167(10) -0.0049(9) -0.0030(8) 0.0032(8)
C2 0.0219(11) 0.0240(12) 0.0163(10) -0.0090(9) -0.0010(8) -0.0023(8)
C3 0.0261(11) 0.0199(11) 0.0185(10) -0.0082(9) -0.0016(8) 0.0000(8)
C4 0.0209(11) 0.0234(12) 0.0176(10) -0.0083(9) -0.0010(8) -0.0008(8)
C5 0.0260(11) 0.0295(12) 0.0159(10) -0.0113(10) -0.0020(8) 0.0037(9)
C6 0.0276(12) 0.0271(12) 0.0235(11) -0.0117(10) -0.0023(8) 0.0068(9)
O7 0.0507(11) 0.0231(9) 0.0269(9) -0.0053(7) -0.0030(7) 0.0022(8)
N7 0.0276(10) 0.0278(11) 0.0179(9) -0.0083(8) -0.0004(7) 0.0063(8)
O8 0.0374(10) 0.0424(11) 0.0373(9) -0.0130(8) -0.0181(7) 0.0075(8)
O9 0.0407(9) 0.0225(8) 0.0128(7) -0.0067(6) -0.0022(6) 0.0032(6)
C10 0.0389(13) 0.0267(13) 0.0234(11) -0.0146(10) -0.0052(9) 0.0078(10)
C11 0.0533(16) 0.0538(17) 0.0213(12) -0.0183(12) -0.0011(10) 0.0088(13)
C12 0.081(2) 0.0403(17) 0.0361(15) -0.0183(13) -0.0059(13) -0.0158(14)
O13 0.0550(11) 0.0229(9) 0.0250(8) -0.0115(7) -0.0140(7) 0.0063(7)
C13 0.0276(12) 0.0224(12) 0.0169(10) -0.0069(9) -0.0022(8) -0.0004(9)
N14 0.0302(10) 0.0173(9) 0.0166(9) -0.0052(7) -0.0053(7) 0.0041(7)
C15 0.0224(11) 0.0214(11) 0.0130(10) -0.0044(9) -0.0019(8) -0.0003(8)
C16 0.0302(12) 0.0230(12) 0.0176(10) -0.0087(9) -0.0032(8) 0.0008(9)
C17 0.0296(12) 0.0209(12) 0.0228(11) -0.0080(10) -0.0032(9) 0.0018(9)
C18 0.0237(11) 0.0196(11) 0.0163(10) -0.0046(9) -0.0017(8) 0.0002(8)
C19 0.0267(11) 0.0224(12) 0.0150(10) -0.0074(9) -0.0021(8) 0.0011(9)
C20 0.0225(11) 0.0174(11) 0.0182(10) -0.0050(9) -0.0011(8) 0.0006(8)
O21 0.0401(9) 0.0207(8) 0.0157(7) -0.0075(6) -0.0073(6) 0.0078(6)
C22 0.0346(12) 0.0249(12) 0.0154(10) -0.0091(9) -0.0030(8) 0.0030(9)
C23 0.0362(14) 0.0292(13) 0.0264(12) -0.0090(11) -0.0033(10) -0.0006(10)
C24 0.0419(14) 0.0265(13) 0.0199(11) -0.0095(10) -0.0022(9) 0.0062(10)
O25 0.0516(11) 0.0182(9) 0.0250(8) -0.0059(7) -0.0159(7) 0.0036(7)
C25 0.0254(12) 0.0199(12) 0.0180(10) -0.0066(9) -0.0005(8) 0.0010(9)
N26 0.0328(10) 0.0153(9) 0.0145(8) -0.0028(7) -0.0052(7) 0.0032(7)
C27 0.0208(11) 0.0220(11) 0.0153(10) -0.0056(9) -0.0004(8) 0.0003(8)
C28 0.0259(11) 0.0227(12) 0.0190(10) -0.0104(9) -0.0011(8) 0.0020(9)
C29 0.0251(12) 0.0187(11) 0.0191(11) -0.0048(9) -0.0016(8) 0.0045(8)
C30 0.0219(11) 0.0210(11) 0.0156(10) -0.0056(9) -0.0002(8) 0.0002(8)
C31 0.0301(12) 0.0214(12) 0.0191(10) -0.0102(9) -0.0027(8) 0.0019(9)
C32 0.0252(11) 0.0167(11) 0.0181(10) -0.0049(9) -0.0022(8) 0.0027(8)
O33 0.0471(10) 0.0182(8) 0.0205(8) -0.0094(7) -0.0114(6) 0.0088(7)
C34 0.0391(13) 0.0201(12) 0.0238(11) -0.0124(10) -0.0073(9) 0.0050(9)
C35 0.0422(14) 0.0302(13) 0.0284(13) -0.0119(11) -0.0027(10) 0.0066(10)
C36 0.0479(15) 0.0243(13) 0.0259(12) -0.0102(10) -0.0034(10) 0.0052(10)
O37 0.0402(9) 0.0267(9) 0.0186(8) -0.0108(7) -0.0065(6) 0.0058(7)
C37 0.0223(11) 0.0214(12) 0.0179(10) -0.0065(9) 0.0007(8) -0.0004(8)
O38 0.0389(9) 0.0199(8) 0.0134(7) -0.0038(6) -0.0057(6) 0.0055(6)
C38 0.0374(13) 0.0251(12) 0.0136(10) -0.0018(9) -0.0079(9) 0.0051(10)
O51 0.079(3) 0.032(2) 0.0289(18) -0.0120(16) -0.0009(17) 0.0018(17)
C52 0.053(4) 0.028(3) 0.031(3) -0.006(3) 0.006(2) 0.004(3)
C53 0.057(5) 0.043(5) 0.033(4) -0.011(4) -0.007(4) 0.014(3)
C54 0.060(5) 0.039(5) 0.050(4) -0.020(4) 0.015(3) -0.002(3)
C55 0.092(6) 0.039(5) 0.036(4) -0.022(4) -0.006(4) 0.003(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.378(3) . ?
C1 C2 1.396(3) . ?
C1 N7 1.476(3) . ?
C2 O9 1.360(2) . ?
C2 C3 1.396(3) . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 C13 1.503(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O7 N7 1.228(2) . ?
N7 O8 1.221(2) . ?
O9 C10 1.451(2) . ?
C10 C12 1.501(3) . ?
C10 C11 1.513(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O13 C13 1.227(2) . ?
C13 N14 1.362(3) . ?
N14 C15 1.410(2) . ?
N14 H14 0.8800 . ?
C15 C16 1.391(3) . ?
C15 C20 1.416(3) . ?
C16 C17 1.397(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.403(3) . ?
C18 C25 1.498(3) . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 O21 1.368(2) . ?
O21 C22 1.461(2) . ?
C22 C23 1.516(3) . ?
C22 C24 1.519(3) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 C25 1.225(2) . ?
C25 N26 1.360(3) . ?
N26 C27 1.417(2) . ?
N26 H26 0.8800 . ?
C27 C28 1.390(3) . ?
C27 C32 1.411(3) . ?
C28 C29 1.390(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.396(3) . ?
C30 C37 1.494(3) . ?
C31 C32 1.386(3) . ?
C31 H31 0.9500 . ?
C32 O33 1.366(2) . ?
O33 C34 1.451(2) . ?
C34 C36 1.513(3) . ?
C34 C35 1.513(3) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
O37 C37 1.213(2) . ?
C37 O38 1.350(2) . ?
O38 C38 1.454(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
O51 C52 1.431(6) . ?
O51 C55 1.435(8) . ?
C52 C53 1.541(8) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.539(10) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C55 1.542(8) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?

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
C6 C1 C2 123.07(18) . . ?
C6 C1 N7 118.16(18) . . ?
C2 C1 N7 118.77(17) . . ?
O9 C2 C3 126.79(18) . . ?
O9 C2 C1 115.67(17) . . ?
C3 C2 C1 117.41(17) . . ?
C2 C3 C4 120.32(19) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.60(18) . . ?
C5 C4 C13 122.79(17) . . ?
C3 C4 C13 116.61(18) . . ?
C4 C5 C6 119.78(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.78(19) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O8 N7 O7 124.50(18) . . ?
O8 N7 C1 118.17(18) . . ?
O7 N7 C1 117.32(17) . . ?
C2 O9 C10 119.61(15) . . ?
O9 C10 C12 109.98(19) . . ?
O9 C10 C11 104.75(17) . . ?
C12 C10 C11 112.6(2) . . ?
O9 C10 H10 109.8 . . ?
C12 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O13 C13 N14 123.34(18) . . ?
O13 C13 C4 121.37(18) . . ?
N14 C13 C4 115.28(18) . . ?
C13 N14 C15 128.18(18) . . ?
C13 N14 H14 115.9 . . ?
C15 N14 H14 115.9 . . ?
C16 C15 N14 124.33(18) . . ?
C16 C15 C20 119.75(17) . . ?
N14 C15 C20 115.92(17) . . ?
C15 C16 C17 119.63(19) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 121.21(19) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.17(18) . . ?
C17 C18 C25 117.65(18) . . ?
C19 C18 C25 123.16(18) . . ?
C20 C19 C18 120.62(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
O21 C20 C19 126.00(18) . . ?
O21 C20 C15 114.36(16) . . ?
C19 C20 C15 119.62(18) . . ?
C20 O21 C22 120.22(14) . . ?
O21 C22 C23 110.32(16) . . ?
O21 C22 C24 105.39(15) . . ?
C23 C22 C24 112.56(19) . . ?
O21 C22 H22 109.5 . . ?
C23 C22 H22 109.5 . . ?
C24 C22 H22 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O25 C25 N26 122.72(18) . . ?
O25 C25 C18 121.51(19) . . ?
N26 C25 C18 115.76(18) . . ?
C25 N26 C27 128.09(17) . . ?
C25 N26 H26 116.0 . . ?
C27 N26 H26 116.0 . . ?
C28 C27 C32 120.22(17) . . ?
C28 C27 N26 124.26(18) . . ?
C32 C27 N26 115.51(17) . . ?
C27 C28 C29 119.40(19) . . ?
C27 C28 H28 120.3 . . ?
C29 C28 H28 120.3 . . ?
C30 C29 C28 120.85(19) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C29 C30 C31 119.84(18) . . ?
C29 C30 C37 122.49(18) . . ?
C31 C30 C37 117.67(18) . . ?
C32 C31 C30 120.20(19) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
O33 C32 C31 126.62(18) . . ?
O33 C32 C27 113.92(16) . . ?
C31 C32 C27 119.46(18) . . ?
C32 O33 C34 120.65(15) . . ?
O33 C34 C36 104.62(16) . . ?
O33 C34 C35 110.92(18) . . ?
C36 C34 C35 111.90(18) . . ?
O33 C34 H34 109.8 . . ?
C36 C34 H34 109.8 . . ?
C35 C34 H34 109.8 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O37 C37 O38 123.28(17) . . ?
O37 C37 C30 124.71(18) . . ?
O38 C37 C30 112.01(17) . . ?
C37 O38 C38 115.63(16) . . ?
O38 C38 H38A 109.5 . . ?
O38 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O38 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C52 O51 C55 105.9(4) . . ?
O51 C52 C53 106.4(5) . . ?
O51 C52 H52A 110.5 . . ?
C53 C52 H52A 110.5 . . ?
O51 C52 H52B 110.5 . . ?
C53 C52 H52B 110.5 . . ?
H52A C52 H52B 108.6 . . ?
C54 C53 C52 104.3(6) . . ?
C54 C53 H53A 110.9 . . ?
C52 C53 H53A 110.9 . . ?
C54 C53 H53B 110.9 . . ?
C52 C53 H53B 110.9 . . ?
H53A C53 H53B 108.9 . . ?
C53 C54 C55 103.1(7) . . ?
C53 C54 H54A 111.1 . . ?
C55 C54 H54A 111.1 . . ?
C53 C54 H54B 111.1 . . ?
C55 C54 H54B 111.1 . . ?
H54A C54 H54B 109.1 . . ?
O51 C55 C54 104.1(5) . . ?
O51 C55 H55A 110.9 . . ?
C54 C55 H55A 110.9 . . ?
O51 C55 H55B 110.9 . . ?
C54 C55 H55B 110.9 . . ?
H55A C55 H55B 108.9 . . ?

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
C6 C1 C2 O9 176.04(18) . . . . ?
N7 C1 C2 O9 -3.6(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
N7 C1 C2 C3 -179.74(19) . . . . ?
O9 C2 C3 C4 -175.50(18) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C2 C3 C4 C13 178.95(18) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C13 C4 C5 C6 -177.93(19) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
N7 C1 C6 C5 -179.24(19) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
C6 C1 N7 O8 120.2(2) . . . . ?
C2 C1 N7 O8 -60.2(3) . . . . ?
C6 C1 N7 O7 -58.5(3) . . . . ?
C2 C1 N7 O7 121.1(2) . . . . ?
C3 C2 O9 C10 -12.5(3) . . . . ?
C1 C2 O9 C10 171.77(18) . . . . ?
C2 O9 C10 C12 -73.0(2) . . . . ?
C2 O9 C10 C11 165.77(17) . . . . ?
C5 C4 C13 O13 -159.9(2) . . . . ?
C3 C4 C13 O13 19.8(3) . . . . ?
C5 C4 C13 N14 20.6(3) . . . . ?
C3 C4 C13 N14 -159.64(18) . . . . ?
O13 C13 N14 C15 4.3(3) . . . . ?
C4 C13 N14 C15 -176.25(18) . . . . ?
C13 N14 C15 C16 -8.6(3) . . . . ?
C13 N14 C15 C20 171.22(18) . . . . ?
N14 C15 C16 C17 178.8(2) . . . . ?
C20 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C16 C17 C18 C25 -178.74(19) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C25 C18 C19 C20 178.57(19) . . . . ?
C18 C19 C20 O21 -178.84(18) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C16 C15 C20 O21 179.40(17) . . . . ?
N14 C15 C20 O21 -0.4(2) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
N14 C15 C20 C19 -178.93(18) . . . . ?
C19 C20 O21 C22 -5.2(3) . . . . ?
C15 C20 O21 C22 176.41(16) . . . . ?
C20 O21 C22 C23 -74.2(2) . . . . ?
C20 O21 C22 C24 164.00(17) . . . . ?
C17 C18 C25 O25 21.8(3) . . . . ?
C19 C18 C25 O25 -156.6(2) . . . . ?
C17 C18 C25 N26 -157.32(18) . . . . ?
C19 C18 C25 N26 24.3(3) . . . . ?
O25 C25 N26 C27 3.5(3) . . . . ?
C18 C25 N26 C27 -177.42(17) . . . . ?
C25 N26 C27 C28 -19.8(3) . . . . ?
C25 N26 C27 C32 161.34(19) . . . . ?
C32 C27 C28 C29 -1.6(3) . . . . ?
N26 C27 C28 C29 179.62(18) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C28 C29 C30 C37 -179.22(19) . . . . ?
C29 C30 C31 C32 -1.5(3) . . . . ?
C37 C30 C31 C32 178.25(18) . . . . ?
C30 C31 C32 O33 -179.66(18) . . . . ?
C30 C31 C32 C27 0.9(3) . . . . ?
C28 C27 C32 O33 -178.86(17) . . . . ?
N26 C27 C32 O33 0.0(2) . . . . ?
C28 C27 C32 C31 0.6(3) . . . . ?
N26 C27 C32 C31 179.52(18) . . . . ?
C31 C32 O33 C34 -1.1(3) . . . . ?
C27 C32 O33 C34 178.31(17) . . . . ?
C32 O33 C34 C36 -163.84(17) . . . . ?
C32 O33 C34 C35 75.3(2) . . . . ?
C29 C30 C37 O37 176.44(19) . . . . ?
C31 C30 C37 O37 -3.3(3) . . . . ?
C29 C30 C37 O38 -3.5(3) . . . . ?
C31 C30 C37 O38 176.76(17) . . . . ?
O37 C37 O38 C38 -3.9(3) . . . . ?
C30 C37 O38 C38 175.95(16) . . . . ?
C55 O51 C52 C53 -34.5(7) . . . . ?
O51 C52 C53 C54 13.2(8) . . . . ?
C52 C53 C54 C55 11.1(10) . . . . ?
C52 O51 C55 C54 41.7(7) . . . . ?
C53 C54 C55 O51 -31.8(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.051




data_C21H26N2O5compound4
_database_code_depnum_ccdc_archive 'CCDC 870275'
#TrackingRef '4.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Benzamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N2 O5'
_chemical_formula_sum            'C21 H26 N2 O5'
_chemical_formula_weight         386.44

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/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   9.0441(7)
_cell_length_b                   13.9383(10)
_cell_length_c                   17.5956(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.421(4)
_cell_angle_gamma                90.00
_cell_volume                     2188.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8184
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.58

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7544
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_process_details   
;
See Sheldrick, G. M. (2002). SADABS.
University of Gottingen, Germany.
;
_exptl_special_details           
;
The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_monochromator  
;
graphite model mounted in "parallel" mode
;
_diffrn_measurement_device_type  
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_detector       'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean 
;
120 microns
;
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            53179
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         28.55
_reflns_number_total             5489
_reflns_number_gt                3170
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_cell_refinement       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction        
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;


_refine_special_details          
;

Measurements were carried out at 150 K on a Bruker-Nonius Apex X8
diffractometer equipped with an Apex II CCD detector and using
graphite monochromated Mo-Kalpha radiation from a FR591 rotating anode
generator. The structure was solved by direct methods and refined
using SHELXL-97. Structure VA1_021 crystallises in space group P21/c
with one molecule of C21 H26 N2 O5 in the asymmetric unit.

All non-hydrogen atoms were refined anisotropically.
All hydrogen atoms could be located in a difference Fourier map but,
in the final stages of the refinement, all H atoms bonded to carbon
were placed in calculated positions and refined using a riding model.

C-H distances: C-H distances: CH3, 0.98\A; CH, 1.00\A; aromatic, 0.95\A.

Those hydrogen atoms bonded to nitrogen could be located
in a difference Fourier map. N-H distances were subsequently
restrained to be 0.88\A.

All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl
and hydroxyl) Ueq of the parent atom.

The HTAB instruction in SHELXL-97 was applied to analyse the hydrogen
bonds present in the structure. The resulting table is present in the
.LST file but is also reproduced here:


Specified hydrogen bonds (with esds except fixed and riding H)

D-H H...A D...A <(DHA)

0.883(19) 2.17(2) 3.006(3) 158(4) N11-H1A...O41_$2
0.880(18) 2.29(3) 3.086(4) 151(3) N11-H1B...O51_$1
0.878(18) 1.91(3) 2.649(3) 141(3) N41-H9...O31


C.Kilner 30 March 2011



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^)+(0.1026P)^2^+1.7358P] 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         5489
_refine_ls_number_parameters     270
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2362
_refine_ls_wR_factor_gt          0.2001
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.0864(3) 0.8611(2) 0.15999(16) 0.0463(7) Uani 1 1 d . . .
H1B H 0.117(4) 1.001(2) 0.139(2) 0.074(12) Uiso 1 1 d D . .
C2 C 0.1545(3) 0.8192(2) 0.10039(16) 0.0466(7) Uani 1 1 d . . .
H2 H 0.1915 0.8594 0.0641 0.056 Uiso 1 1 calc R . .
C3 C 0.1674(3) 0.7192(2) 0.09475(15) 0.0419(6) Uani 1 1 d . . .
H9 H 0.191(4) 0.544(2) 0.0530(16) 0.066(10) Uiso 1 1 d D . .
H1A H 0.040(5) 0.980(3) 0.2065(16) 0.086(13) Uiso 1 1 d D . .
C4 C 0.1198(3) 0.6558(2) 0.15056(14) 0.0382(6) Uani 1 1 d . . .
C5 C 0.0556(3) 0.7008(2) 0.21024(15) 0.0414(6) Uani 1 1 d . . .
H5 H 0.0241 0.6613 0.2486 0.050 Uiso 1 1 calc R . .
C6 C 0.0368(3) 0.7993(2) 0.21524(16) 0.0446(7) Uani 1 1 d . . .
H6 H -0.0091 0.8255 0.2555 0.054 Uiso 1 1 calc R . .
N11 N 0.0688(4) 0.9598(2) 0.16367(18) 0.0648(8) Uani 1 1 d D . .
O31 O 0.2297(3) 0.67593(16) 0.03583(12) 0.0552(6) Uani 1 1 d . . .
C32 C 0.2841(4) 0.7316(2) -0.02464(18) 0.0555(8) Uani 1 1 d . . .
H32 H 0.3497 0.7847 -0.0003 0.067 Uiso 1 1 calc R . .
C33 C 0.1538(5) 0.7744(3) -0.0805(2) 0.0754(11) Uani 1 1 d . . .
H33A H 0.0854 0.7231 -0.1019 0.113 Uiso 1 1 calc R . .
H33B H 0.1925 0.8073 -0.1224 0.113 Uiso 1 1 calc R . .
H33C H 0.0997 0.8204 -0.0530 0.113 Uiso 1 1 calc R . .
C34 C 0.3781(5) 0.6614(3) -0.0621(2) 0.0784(12) Uani 1 1 d . . .
H34A H 0.4520 0.6311 -0.0224 0.118 Uiso 1 1 calc R . .
H34B H 0.4302 0.6957 -0.0985 0.118 Uiso 1 1 calc R . .
H34C H 0.3131 0.6120 -0.0896 0.118 Uiso 1 1 calc R . .
O41 O 0.1080(3) 0.49993(16) 0.20932(13) 0.0634(7) Uani 1 1 d . . .
N41 N 0.1762(3) 0.50410(18) 0.08964(13) 0.0452(6) Uani 1 1 d D . .
C41 C 0.1343(3) 0.5476(2) 0.15299(15) 0.0410(6) Uani 1 1 d . . .
C42 C 0.1992(3) 0.4050(2) 0.07443(15) 0.0405(6) Uani 1 1 d . . .
C43 C 0.1908(3) 0.3789(2) -0.00405(15) 0.0428(6) Uani 1 1 d . . .
H43 H 0.1669 0.4257 -0.0434 0.051 Uiso 1 1 calc R . .
C44 C 0.2178(3) 0.2840(2) -0.02313(16) 0.0441(7) Uani 1 1 d . . .
H44 H 0.2118 0.2671 -0.0758 0.053 Uiso 1 1 calc R . .
C45 C 0.2537(3) 0.2123(2) 0.03384(15) 0.0425(6) Uani 1 1 d . . .
C46 C 0.2643(3) 0.2391(2) 0.11302(15) 0.0436(6) Uani 1 1 d . . .
C47 C 0.2351(3) 0.3351(2) 0.13275(15) 0.0415(6) Uani 1 1 d . . .
H47 H 0.2396 0.3524 0.1853 0.050 Uiso 1 1 calc R . .
O51 O 0.2438(3) 0.03687(17) 0.03996(13) 0.0655(7) Uani 1 1 d . . .
C51 C 0.2762(4) 0.1108(2) 0.00810(17) 0.0485(7) Uani 1 1 d . . .
O52 O 0.3380(3) 0.11019(15) -0.05753(13) 0.0606(6) Uani 1 1 d . . .
C53 C 0.3504(5) 0.0163(3) -0.0945(2) 0.0724(11) Uani 1 1 d . . .
H53A H 0.4033 -0.0288 -0.0568 0.109 Uiso 1 1 calc R . .
H53B H 0.4063 0.0237 -0.1374 0.109 Uiso 1 1 calc R . .
H53C H 0.2499 -0.0085 -0.1140 0.109 Uiso 1 1 calc R . .
O61 O 0.3051(3) 0.16750(16) 0.16695(12) 0.0598(6) Uani 1 1 d . . .
C62 C 0.3519(4) 0.1929(3) 0.24908(17) 0.0543(8) Uani 1 1 d . . .
H62 H 0.2725 0.2334 0.2665 0.065 Uiso 1 1 calc R . .
C63 C 0.3623(5) 0.0960(3) 0.2924(2) 0.0772(12) Uani 1 1 d . . .
H63A H 0.2645 0.0641 0.2831 0.116 Uiso 1 1 calc R . .
H63B H 0.3921 0.1074 0.3478 0.116 Uiso 1 1 calc R . .
H63C H 0.4370 0.0551 0.2739 0.116 Uiso 1 1 calc R . .
C64 C 0.5004(4) 0.2477(3) 0.2619(2) 0.0808(12) Uani 1 1 d . . .
H64A H 0.5787 0.2079 0.2455 0.121 Uiso 1 1 calc R . .
H64B H 0.5282 0.2632 0.3167 0.121 Uiso 1 1 calc R . .
H64C H 0.4894 0.3072 0.2318 0.121 Uiso 1 1 calc R . .

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
C1 0.0538(17) 0.0440(16) 0.0432(15) -0.0027(13) 0.0147(13) -0.0015(13)
C2 0.0550(17) 0.0460(16) 0.0419(15) 0.0045(12) 0.0167(13) -0.0011(13)
C3 0.0447(15) 0.0484(16) 0.0347(13) -0.0021(11) 0.0126(11) -0.0005(12)
C4 0.0388(14) 0.0428(15) 0.0334(13) -0.0024(11) 0.0074(10) -0.0037(11)
C5 0.0447(15) 0.0471(16) 0.0336(13) 0.0001(11) 0.0104(11) -0.0062(12)
C6 0.0504(16) 0.0481(17) 0.0377(14) -0.0055(12) 0.0138(12) -0.0021(13)
N11 0.093(2) 0.0461(16) 0.0666(19) -0.0007(14) 0.0451(17) 0.0010(15)
O31 0.0764(15) 0.0486(12) 0.0487(12) 0.0008(9) 0.0346(11) 0.0023(10)
C32 0.070(2) 0.0566(19) 0.0462(17) 0.0034(14) 0.0277(15) -0.0036(16)
C33 0.082(3) 0.089(3) 0.054(2) -0.0036(19) 0.0074(18) -0.014(2)
C34 0.086(3) 0.086(3) 0.074(2) -0.010(2) 0.044(2) -0.012(2)
O41 0.0973(18) 0.0473(13) 0.0549(13) 0.0063(10) 0.0405(12) 0.0007(12)
N41 0.0590(15) 0.0425(14) 0.0367(12) 0.0033(10) 0.0155(11) 0.0024(11)
C41 0.0418(14) 0.0461(16) 0.0362(13) -0.0003(12) 0.0091(11) -0.0036(12)
C42 0.0405(14) 0.0441(15) 0.0374(13) -0.0010(11) 0.0079(11) 0.0005(11)
C43 0.0496(16) 0.0438(16) 0.0347(13) 0.0061(11) 0.0058(11) 0.0025(12)
C44 0.0500(16) 0.0490(17) 0.0335(13) -0.0027(12) 0.0069(11) -0.0025(13)
C45 0.0462(15) 0.0429(15) 0.0391(14) 0.0009(12) 0.0087(11) 0.0022(12)
C46 0.0439(15) 0.0491(17) 0.0374(14) 0.0058(12) 0.0054(11) 0.0029(12)
C47 0.0426(15) 0.0501(16) 0.0316(13) 0.0009(11) 0.0056(11) 0.0008(12)
O51 0.0952(18) 0.0458(13) 0.0610(14) 0.0046(11) 0.0296(13) -0.0014(12)
C51 0.0577(18) 0.0482(17) 0.0397(15) 0.0005(13) 0.0083(13) 0.0003(14)
O52 0.0908(17) 0.0457(12) 0.0508(13) -0.0027(10) 0.0276(11) 0.0020(11)
C53 0.109(3) 0.053(2) 0.057(2) -0.0101(16) 0.019(2) 0.011(2)
O61 0.0872(17) 0.0533(13) 0.0377(11) 0.0076(9) 0.0063(10) 0.0142(12)
C62 0.0555(18) 0.068(2) 0.0390(15) 0.0091(14) 0.0062(13) 0.0118(15)
C63 0.104(3) 0.075(3) 0.050(2) 0.0152(18) 0.0047(19) 0.017(2)
C64 0.0476(19) 0.119(4) 0.072(2) 0.017(2) -0.0021(17) 0.005(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N11 1.387(4) . ?
C1 C2 1.425(4) . ?
C1 C6 1.426(4) . ?
C2 C3 1.404(4) . ?
C2 H2 0.9500 . ?
C3 O31 1.395(3) . ?
C3 C4 1.438(4) . ?
C4 C5 1.425(4) . ?
C4 C41 1.514(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N11 H1B 0.880(18) . ?
N11 H1A 0.883(19) . ?
O31 C32 1.465(3) . ?
C32 C34 1.516(5) . ?
C32 C33 1.527(5) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
O41 C41 1.249(3) . ?
N41 C41 1.376(3) . ?
N41 C42 1.429(4) . ?
N41 H9 0.878(18) . ?
C42 C47 1.414(4) . ?
C42 C43 1.418(4) . ?
C43 C44 1.395(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.415(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.430(4) . ?
C45 C51 1.509(4) . ?
C46 O61 1.385(3) . ?
C46 C47 1.417(4) . ?
C47 H47 0.9500 . ?
O51 C51 1.232(4) . ?
C51 O52 1.363(4) . ?
O52 C53 1.474(4) . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
O61 C62 1.481(4) . ?
C62 C64 1.529(5) . ?
C62 C63 1.547(5) . ?
C62 H62 1.0000 . ?
C63 H63A 0.9800 . ?
C63 H63B 0.9800 . ?
C63 H63C 0.9800 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N11 C1 C2 120.5(3) . . ?
N11 C1 C6 121.1(3) . . ?
C2 C1 C6 118.4(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
O31 C3 C2 122.0(2) . . ?
O31 C3 C4 116.4(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 115.9(2) . . ?
C5 C4 C41 117.5(2) . . ?
C3 C4 C41 126.6(2) . . ?
C6 C5 C4 123.4(2) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 N11 H1B 123(3) . . ?
C1 N11 H1A 114(3) . . ?
H1B N11 H1A 118(4) . . ?
C3 O31 C32 122.4(2) . . ?
O31 C32 C34 104.7(3) . . ?
O31 C32 C33 111.0(3) . . ?
C34 C32 C33 113.7(3) . . ?
O31 C32 H32 109.1 . . ?
C34 C32 H32 109.1 . . ?
C33 C32 H32 109.1 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C41 N41 C42 130.3(2) . . ?
C41 N41 H9 114(2) . . ?
C42 N41 H9 115(2) . . ?
O41 C41 N41 121.5(3) . . ?
O41 C41 C4 121.7(2) . . ?
N41 C41 C4 116.8(2) . . ?
C47 C42 C43 119.9(3) . . ?
C47 C42 N41 123.6(2) . . ?
C43 C42 N41 116.4(2) . . ?
C44 C43 C42 119.6(2) . . ?
C44 C43 H43 120.2 . . ?
C42 C43 H43 120.2 . . ?
C43 C44 C45 121.9(3) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C44 C45 C46 118.5(3) . . ?
C44 C45 C51 118.4(2) . . ?
C46 C45 C51 123.1(2) . . ?
O61 C46 C47 123.5(2) . . ?
O61 C46 C45 116.6(3) . . ?
C47 C46 C45 120.0(2) . . ?
C42 C47 C46 120.2(2) . . ?
C42 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
O51 C51 O52 122.8(3) . . ?
O51 C51 C45 126.5(3) . . ?
O52 C51 C45 110.8(2) . . ?
C51 O52 C53 116.9(3) . . ?
O52 C53 H53A 109.5 . . ?
O52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C46 O61 C62 119.9(2) . . ?
O61 C62 C64 111.6(3) . . ?
O61 C62 C63 104.9(3) . . ?
C64 C62 C63 112.5(3) . . ?
O61 C62 H62 109.3 . . ?
C64 C62 H62 109.3 . . ?
C63 C62 H62 109.3 . . ?
C62 C63 H63A 109.5 . . ?
C62 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C62 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C62 C64 H64A 109.5 . . ?
C62 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C62 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C1 C2 C3 -177.6(3) . . . . ?
C6 C1 C2 C3 2.3(4) . . . . ?
C1 C2 C3 O31 178.2(3) . . . . ?
C1 C2 C3 C4 -3.2(4) . . . . ?
O31 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C5 1.6(4) . . . . ?
O31 C3 C4 C41 1.8(4) . . . . ?
C2 C3 C4 C41 -176.9(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C41 C4 C5 C6 179.5(3) . . . . ?
C4 C5 C6 C1 -1.7(4) . . . . ?
N11 C1 C6 C5 180.0(3) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 O31 C32 -0.8(4) . . . . ?
C4 C3 O31 C32 -179.5(3) . . . . ?
C3 O31 C32 C34 165.1(3) . . . . ?
C3 O31 C32 C33 -71.8(4) . . . . ?
C42 N41 C41 O41 -0.7(5) . . . . ?
C42 N41 C41 C4 -180.0(3) . . . . ?
C5 C4 C41 O41 -8.2(4) . . . . ?
C3 C4 C41 O41 170.3(3) . . . . ?
C5 C4 C41 N41 171.0(2) . . . . ?
C3 C4 C41 N41 -10.5(4) . . . . ?
C41 N41 C42 C47 -24.0(5) . . . . ?
C41 N41 C42 C43 158.7(3) . . . . ?
C47 C42 C43 C44 0.1(4) . . . . ?
N41 C42 C43 C44 177.5(3) . . . . ?
C42 C43 C44 C45 0.0(4) . . . . ?
C43 C44 C45 C46 -0.8(4) . . . . ?
C43 C44 C45 C51 178.0(3) . . . . ?
C44 C45 C46 O61 -177.7(3) . . . . ?
C51 C45 C46 O61 3.5(4) . . . . ?
C44 C45 C46 C47 1.6(4) . . . . ?
C51 C45 C46 C47 -177.1(3) . . . . ?
C43 C42 C47 C46 0.7(4) . . . . ?
N41 C42 C47 C46 -176.5(3) . . . . ?
O61 C46 C47 C42 177.7(3) . . . . ?
C45 C46 C47 C42 -1.6(4) . . . . ?
C44 C45 C51 O51 -146.0(3) . . . . ?
C46 C45 C51 O51 32.8(5) . . . . ?
C44 C45 C51 O52 33.5(4) . . . . ?
C46 C45 C51 O52 -147.7(3) . . . . ?
O51 C51 O52 C53 6.4(5) . . . . ?
C45 C51 O52 C53 -173.2(3) . . . . ?
C47 C46 O61 C62 -13.2(4) . . . . ?
C45 C46 O61 C62 166.1(3) . . . . ?
C46 O61 C62 C64 -67.2(4) . . . . ?
C46 O61 C62 C63 170.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H1A O41 0.883(19) 2.17(2) 3.006(3) 158(4) 2
N11 H1B O51 0.880(18) 2.29(3) 3.086(4) 151(3) 1_565
N41 H9 O31 0.878(18) 1.91(3) 2.649(3) 141(3) .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.55
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.054