# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350

_publ_contact_author             
;
"Itzia I. Padilla-Mart\'inez^*^"
Unidad Profesional Interdisciplinaria de Biotecnolog\'ia
Instituto Polit\'ecnico Nacional
Avenida Acueducto s/n
Barrio La Laguna Ticom\'an
M\'exico D. F. 07340, M\'exico.
;
_publ_contact_author_phone       '015 729 6000 EXT 56324'
_publ_contact_author_fax         '015 729 6000 EXT 56325'
_publ_contact_author_email       ipadillamar@ipn.mx
_publ_requested_category         FO

loop_
_publ_author_name
_publ_author_address
'Juan Saulo Gonzalez-Gonzalez'
; Facultad de Ciencias Qu\'imicas
Universidad de Colima
Carretera Coquimatl\'an-Colima
Coquimatl\'an Colima, M\'exico 28400.
;
F.J.Martinez-Martinez
; Facultad de Ciencias Qu\'imicas
Universidad de Colima
Carretera Coquimatl\'an-Colima
Coquimatl\'an Colima, M\'exico 28400.
;
E.V.Garcia-Baez
; Unidad Profesional Interdisciplinaria de Biotecnolog\'ia
Instituto Polit\'ecnico Nacional
Avenida Acueducto s/n
Barrio La Laguna Ticom\'an
M\'exico D. F. 07340, M\'exico.
;
'Ana L. Peraza-Campos'
; Facultad de Ciencias Qu\'imicas
Universidad de Colima
Carretera Coquimatl\'an-Colima
Coquimatl\'an Colima, M\'exico 28400.
;
I.I.Padilla-Martinez
; Unidad Profesional Interdisciplinaria de Biotecnolog\'ia
Instituto Polit\'ecnico Nacional
Avenida Acueducto s/n
Barrio La Laguna Ticom\'an
M\'exico D. F. 07340, M\'exico.
;

_publ_section_title              
;
?
;

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;
_publ_contact_author_name        'Itzia I. Padilla-Martinez^^'

data_497
_database_code_depnum_ccdc_archive 'CCDC 795129'
#TrackingRef 'saulo1.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Diethyl N,N'-[1,3-(2,4,6-trimethyl)phenylene]dioxamalate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 N2 O6'
_chemical_formula_weight         350.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.0020(3)
_cell_length_b                   15.7340(5)
_cell_length_c                   14.3370(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.76(4)
_cell_angle_gamma                90
_cell_volume                     1760.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            10213
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3043
_reflns_number_gt                2197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'CRYSTALS (Betteridge <i>et al.</i>, 2003)'
_computing_molecular_graphics    'CAMERON (Watkin <i>et al.</i>, 1996)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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^)+(0.1803P)^2^+0.9092P] 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       0.084(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.2647
_refine_ls_wR_factor_gt          0.2083
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.056
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani -0.0046(3) 0.44209(15) -0.13980(16) 1.000 0.0328(8) . .
O9 O Uani -0.0518(3) 0.23559(17) -0.22888(19) 1.000 0.0414(10) . .
O10 O Uani -0.1843(3) 0.35590(17) -0.28886(19) 1.000 0.0413(9) . .
O28 O Uani 0.3426(3) 0.31231(15) 0.31360(16) 1.000 0.0317(8) . .
O29 O Uani 0.0568(3) 0.46691(17) 0.35752(18) 1.000 0.0407(9) . .
O30 O Uani 0.2066(3) 0.36844(16) 0.45490(16) 1.000 0.0320(8) . .
N7 N Uani 0.1816(3) 0.33126(16) -0.10308(18) 1.000 0.0229(8) . .
N27 N Uani 0.2460(3) 0.43023(18) 0.22507(18) 1.000 0.0239(8) . .
C1 C Uani 0.2877(4) 0.3649(2) -0.0172(2) 1.000 0.0216(10) . .
C2 C Uani 0.2132(4) 0.38203(19) 0.0608(2) 1.000 0.0213(9) . .
C3 C Uani 0.3211(4) 0.4100(2) 0.1450(2) 1.000 0.0241(10) . .
C4 C Uani 0.4978(4) 0.4199(2) 0.1545(2) 1.000 0.0276(11) . .
C5 C Uani 0.5632(4) 0.4029(2) 0.0741(2) 1.000 0.0285(11) . .
C6 C Uani 0.4632(4) 0.3760(2) -0.0118(2) 1.000 0.0251(10) . .
C8 C Uani 0.0413(4) 0.3697(2) -0.1528(2) 1.000 0.0234(10) . .
C9 C Uani -0.0695(4) 0.3114(2) -0.2279(2) 1.000 0.0270(11) . .
C11 C Uani -0.2988(6) 0.3083(3) -0.3647(3) 1.000 0.0588(16) . .
C12 C Uani -0.3692(6) 0.3687(4) -0.4427(3) 1.000 0.0629(18) . .
C28 C Uani 0.2598(4) 0.3783(2) 0.3006(2) 1.000 0.0237(10) . .
C29 C Uani 0.1609(4) 0.4110(2) 0.3733(2) 1.000 0.0260(10) . .
C31 C Uani 0.1255(6) 0.3969(3) 0.5313(3) 1.000 0.0499(16) . .
C32 C Uani 0.2076(5) 0.3510(3) 0.6210(3) 1.000 0.0446(16) . .
C33 C Uani 0.0261(4) 0.3678(2) 0.0562(2) 1.000 0.0269(11) . .
C34 C Uani 0.5418(5) 0.3594(2) -0.0966(3) 1.000 0.0347(11) . .
C35 C Uani 0.6140(5) 0.4458(3) 0.2479(3) 1.000 0.0377(11) . .
H5 H Uiso 0.68253 0.41026 0.07872 1.000 0.0344 . .
H7 H Uiso 0.21078 0.28220 -0.12430 1.000 0.0275 . .
H11A H Uiso -0.23479 0.26241 -0.38878 1.000 0.0705 . .
H11B H Uiso -0.39283 0.28226 -0.33984 1.000 0.0705 . .
H12A H Uiso -0.43217 0.41378 -0.41815 1.000 0.0941 . .
H12B H Uiso -0.27518 0.39370 -0.46715 1.000 0.0941 . .
H12C H Uiso -0.44697 0.33845 -0.49454 1.000 0.0941 . .
H27 H Uiso 0.18927 0.47823 0.22429 1.000 0.0287 . .
H31A H Uiso 0.14068 0.45903 0.54058 1.000 0.0597 . .
H31B H Uiso 0.00122 0.38445 0.51425 1.000 0.0597 . .
H32A H Uiso 0.15539 0.36966 0.67331 1.000 0.0671 . .
H32B H Uiso 0.19075 0.28971 0.61140 1.000 0.0671 . .
H32C H Uiso 0.33057 0.36370 0.63725 1.000 0.0671 . .
H33A H Uiso -0.00141 0.30757 0.04357 1.000 0.0401 . .
H33B H Uiso -0.00049 0.38400 0.11733 1.000 0.0401 . .
H33C H Uiso -0.04209 0.40239 0.00479 1.000 0.0401 . .
H34A H Uiso 0.46430 0.37989 -0.15502 1.000 0.0519 . .
H34B H Uiso 0.65169 0.38920 -0.08777 1.000 0.0519 . .
H34C H Uiso 0.56040 0.29817 -0.10220 1.000 0.0519 . .
H35A H Uiso 0.63290 0.39708 0.29155 1.000 0.0566 . .
H35B H Uiso 0.72397 0.46511 0.23624 1.000 0.0566 . .
H35C H Uiso 0.56049 0.49208 0.27663 1.000 0.0566 . .

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
O8 0.0376(14) 0.0301(16) 0.0275(13) -0.0016(10) 0.0005(10) 0.0091(10)
O9 0.0400(15) 0.0326(18) 0.0461(17) -0.0079(12) -0.0026(12) 0.0010(11)
O10 0.0334(15) 0.0391(17) 0.0424(16) -0.0092(12) -0.0108(12) 0.0054(11)
O28 0.0359(14) 0.0288(14) 0.0321(14) 0.0054(10) 0.0110(11) 0.0095(10)
O29 0.0459(16) 0.0433(17) 0.0347(15) 0.0052(11) 0.0128(12) 0.0200(13)
O30 0.0336(14) 0.0395(16) 0.0247(13) 0.0026(10) 0.0104(10) 0.0078(10)
N7 0.0246(14) 0.0183(15) 0.0257(15) -0.0031(10) 0.0052(11) 0.0014(10)
N27 0.0256(15) 0.0238(15) 0.0219(14) -0.0014(11) 0.0043(11) 0.0059(11)
C1 0.0233(17) 0.0192(17) 0.0217(17) 0.0017(12) 0.0034(13) 0.0004(12)
C2 0.0208(16) 0.0144(16) 0.0281(17) 0.0024(12) 0.0042(13) 0.0023(12)
C3 0.0259(17) 0.0229(18) 0.0235(17) 0.0007(13) 0.0054(13) 0.0023(13)
C4 0.0216(17) 0.030(2) 0.0297(19) -0.0013(14) 0.0027(14) -0.0003(13)
C5 0.0182(16) 0.030(2) 0.037(2) -0.0023(15) 0.0052(14) -0.0022(13)
C6 0.0243(17) 0.0236(18) 0.0282(18) 0.0017(13) 0.0076(14) 0.0012(13)
C8 0.0229(16) 0.027(2) 0.0210(17) 0.0017(12) 0.0065(13) 0.0019(13)
C9 0.0242(17) 0.030(2) 0.0268(18) -0.0034(14) 0.0054(14) 0.0032(14)
C11 0.040(2) 0.061(3) 0.061(3) -0.027(2) -0.020(2) 0.008(2)
C12 0.037(2) 0.103(4) 0.041(3) -0.010(2) -0.008(2) -0.001(2)
C28 0.0241(17) 0.0237(18) 0.0217(17) -0.0013(13) 0.0015(13) -0.0004(13)
C29 0.0264(17) 0.0250(19) 0.0260(18) -0.0008(13) 0.0044(14) -0.0001(14)
C31 0.060(3) 0.062(3) 0.035(2) 0.004(2) 0.026(2) 0.018(2)
C32 0.057(3) 0.052(3) 0.029(2) -0.0030(17) 0.0184(19) -0.009(2)
C33 0.0213(17) 0.033(2) 0.0267(18) 0.0017(14) 0.0057(14) 0.0006(13)
C34 0.0312(19) 0.041(2) 0.035(2) -0.0051(16) 0.0141(16) -0.0030(15)
C35 0.0310(19) 0.040(2) 0.038(2) -0.0071(17) -0.0012(16) -0.0025(16)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.224(4) . . yes
O9 C9 1.202(4) . . yes
O10 C9 1.320(4) . . yes
O10 C11 1.464(5) . . yes
O28 C28 1.224(4) . . yes
O29 C29 1.198(4) . . yes
O30 C29 1.327(4) . . yes
O30 C31 1.461(5) . . yes
N7 C1 1.434(4) . . yes
N7 C8 1.335(4) . . yes
N27 C3 1.444(4) . . yes
N27 C28 1.342(4) . . yes
N7 H7 0.8800 . . no
N27 H27 0.8800 . . no
C1 C6 1.400(5) . . no
C1 C2 1.405(4) . . no
C2 C3 1.391(4) . . no
C2 C33 1.501(5) . . no
C3 C4 1.399(5) . . no
C4 C5 1.393(4) . . no
C4 C35 1.508(5) . . no
C5 C6 1.379(4) . . no
C6 C34 1.510(5) . . no
C8 C9 1.538(4) . . no
C11 C12 1.481(7) . . no
C28 C29 1.530(4) . . no
C31 C32 1.495(6) . . no
C5 H5 0.9500 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no
C12 H12A 0.9800 . . no
C12 H12B 0.9800 . . no
C12 H12C 0.9800 . . no
C31 H31A 0.9900 . . no
C31 H31B 0.9900 . . no
C32 H32A 0.9800 . . no
C32 H32B 0.9800 . . no
C32 H32C 0.9800 . . no
C33 H33A 0.9800 . . no
C33 H33B 0.9800 . . no
C33 H33C 0.9800 . . no
C34 H34A 0.9800 . . no
C34 H34B 0.9800 . . no
C34 H34C 0.9800 . . no
C35 H35A 0.9800 . . no
C35 H35B 0.9800 . . no
C35 H35C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11 116.8(3) . . . yes
C29 O30 C31 115.1(3) . . . yes
C1 N7 C8 124.1(3) . . . yes
C3 N27 C28 122.2(3) . . . yes
C8 N7 H7 118.00 . . . no
C1 N7 H7 118.00 . . . no
C28 N27 H27 119.00 . . . no
C3 N27 H27 119.00 . . . no
C2 C1 C6 121.9(3) . . . no
N7 C1 C6 119.3(3) . . . yes
N7 C1 C2 118.7(3) . . . yes
C1 C2 C33 122.1(3) . . . no
C3 C2 C33 120.5(3) . . . no
C1 C2 C3 117.4(3) . . . no
N27 C3 C2 118.2(3) . . . yes
N27 C3 C4 119.2(3) . . . yes
C2 C3 C4 122.7(3) . . . no
C3 C4 C5 117.0(3) . . . no
C3 C4 C35 121.9(3) . . . no
C5 C4 C35 121.1(3) . . . no
C4 C5 C6 123.2(3) . . . no
C1 C6 C5 117.7(3) . . . no
C1 C6 C34 121.7(3) . . . no
C5 C6 C34 120.6(3) . . . no
N7 C8 C9 113.0(3) . . . yes
O8 C8 N7 125.9(3) . . . yes
O8 C8 C9 121.1(3) . . . yes
O9 C9 C8 123.3(3) . . . yes
O10 C9 C8 110.9(3) . . . yes
O9 C9 O10 125.8(3) . . . yes
O10 C11 C12 107.7(4) . . . yes
O28 C28 N27 125.8(3) . . . yes
O28 C28 C29 121.7(3) . . . yes
N27 C28 C29 112.5(3) . . . yes
O29 C29 C28 124.1(3) . . . yes
O30 C29 C28 110.3(3) . . . yes
O29 C29 O30 125.6(3) . . . yes
O30 C31 C32 108.3(4) . . . yes
C4 C5 H5 118.00 . . . no
C6 C5 H5 118.00 . . . no
O10 C11 H11A 110.00 . . . no
O10 C11 H11B 110.00 . . . no
C12 C11 H11A 110.00 . . . no
C12 C11 H11B 110.00 . . . no
H11A C11 H11B 108.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
C11 C12 H12C 109.00 . . . no
H12A C12 H12B 110.00 . . . no
H12A C12 H12C 109.00 . . . no
H12B C12 H12C 109.00 . . . no
O30 C31 H31A 110.00 . . . no
O30 C31 H31B 110.00 . . . no
C32 C31 H31A 110.00 . . . no
C32 C31 H31B 110.00 . . . no
H31A C31 H31B 108.00 . . . no
C31 C32 H32A 109.00 . . . no
C31 C32 H32B 110.00 . . . no
C31 C32 H32C 109.00 . . . no
H32A C32 H32B 109.00 . . . no
H32A C32 H32C 109.00 . . . no
H32B C32 H32C 110.00 . . . no
C2 C33 H33A 109.00 . . . no
C2 C33 H33B 109.00 . . . no
C2 C33 H33C 110.00 . . . no
H33A C33 H33B 109.00 . . . no
H33A C33 H33C 109.00 . . . no
H33B C33 H33C 109.00 . . . no
C6 C34 H34A 109.00 . . . no
C6 C34 H34B 110.00 . . . no
C6 C34 H34C 109.00 . . . no
H34A C34 H34B 109.00 . . . no
H34A C34 H34C 109.00 . . . no
H34B C34 H34C 109.00 . . . no
C4 C35 H35A 109.00 . . . no
C4 C35 H35B 109.00 . . . no
C4 C35 H35C 109.00 . . . no
H35A C35 H35B 110.00 . . . no
H35A C35 H35C 109.00 . . . no
H35B C35 H35C 109.00 . . . no

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
C11 O10 C9 C8 179.9(3) . . . . no
C9 O10 C11 C12 -159.4(3) . . . . no
C11 O10 C9 O9 -0.6(5) . . . . no
C29 O30 C31 C32 -172.4(3) . . . . no
C31 O30 C29 C28 177.4(3) . . . . no
C31 O30 C29 O29 -2.9(5) . . . . no
C1 N7 C8 C9 -167.1(3) . . . . no
C1 N7 C8 O8 9.5(5) . . . . no
C8 N7 C1 C6 -125.0(3) . . . . no
C8 N7 C1 C2 58.0(4) . . . . no
C3 N27 C28 C29 -176.6(3) . . . . no
C28 N27 C3 C4 -76.6(4) . . . . no
C3 N27 C28 O28 4.4(5) . . . . no
C28 N27 C3 C2 104.0(3) . . . . no
C6 C1 C2 C33 -178.2(3) . . . . no
N7 C1 C6 C5 -175.6(3) . . . . no
C2 C1 C6 C34 -178.6(3) . . . . no
C6 C1 C2 C3 -0.6(5) . . . . no
N7 C1 C2 C33 -1.2(4) . . . . no
C2 C1 C6 C5 1.4(5) . . . . no
N7 C1 C6 C34 4.5(5) . . . . no
N7 C1 C2 C3 176.4(3) . . . . no
C33 C2 C3 C4 176.5(3) . . . . no
C33 C2 C3 N27 -4.1(4) . . . . no
C1 C2 C3 N27 178.3(3) . . . . no
C1 C2 C3 C4 -1.1(5) . . . . no
N27 C3 C4 C5 -177.5(3) . . . . no
N27 C3 C4 C35 3.9(5) . . . . no
C2 C3 C4 C5 1.9(5) . . . . no
C2 C3 C4 C35 -176.7(3) . . . . no
C35 C4 C5 C6 177.5(3) . . . . no
C3 C4 C5 C6 -1.1(5) . . . . no
C4 C5 C6 C1 -0.5(5) . . . . no
C4 C5 C6 C34 179.5(3) . . . . no
N7 C8 C9 O10 -166.1(3) . . . . no
N7 C8 C9 O9 14.3(4) . . . . no
O8 C8 C9 O9 -162.5(3) . . . . no
O8 C8 C9 O10 17.1(4) . . . . no
O28 C28 C29 O29 -167.4(3) . . . . no
O28 C28 C29 O30 12.3(4) . . . . no
N27 C28 C29 O29 13.5(5) . . . . no
N27 C28 C29 O30 -166.8(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 O10 2.668(4) . . no
O8 C2 3.160(4) . . no
O8 C33 3.003(4) . . no
O8 N27 2.867(4) . 3_565 no
O8 C33 3.241(4) . 3_565 no
O9 C29 3.043(4) . 4_554 no
O9 C28 3.024(4) . 4_554 no
O9 N7 2.742(4) . . no
O9 O28 3.170(3) . 4_554 no
O10 O8 2.668(4) . . no
O10 O29 3.198(4) . 3_565 no
O28 C34 3.254(4) . 4_555 no
O28 O30 2.654(3) . . no
O28 C35 3.304(5) . . no
O28 O9 3.170(3) . 4_555 no
O28 N7 2.978(3) . 4_555 no
O28 C4 3.296(4) . . no
O29 C31 3.207(5) . 3_566 no
O29 N27 2.739(4) . . no
O29 O10 3.198(4) . 3_565 no
O30 O28 2.654(3) . . no
O30 N7 3.245(4) . 4_555 no
O30 C12 3.388(5) . 1_656 no
O8 H27 2.1100 . 3_565 no
O8 H33B 2.7500 . 3_565 no
O8 H33C 2.2500 . . no
O9 H11A 2.4700 . . no
O9 H7 2.4100 . . no
O10 H27 2.7700 . 3_565 no
O10 H32A 2.8900 . 1_554 no
O28 H35A 2.7600 . . no
O28 H34C 2.5700 . 4_555 no
O28 H12C 2.9200 . 1_656 no
O28 H7 2.1300 . 4_555 no
O29 H31B 2.7200 . . no
O29 H31A 2.6500 . 3_566 no
O29 H27 2.3900 . . no
O29 H31A 2.5600 . . no
O29 H35B 2.8400 . 1_455 no
O30 H12C 2.7500 . 1_656 no
O30 H7 2.6300 . 4_555 no
N7 O9 2.742(4) . . no
N7 O28 2.978(3) . 4_554 no
N7 O30 3.245(4) . 4_554 no
N27 O29 2.739(4) . . no
N27 O8 2.867(4) . 3_565 no
N7 H33A 2.8400 . . no
N7 H34A 2.6500 . . no
N7 H33C 2.8400 . . no
N27 H33B 2.3400 . . no
N27 H35C 2.6500 . . no
C2 O8 3.160(4) . . no
C4 O28 3.296(4) . . no
C4 C34 3.568(4) . 3_665 no
C5 C6 3.586(4) . 3_665 no
C5 C11 3.550(6) . 4_655 no
C6 C5 3.586(4) . 3_665 no
C8 C33 3.026(4) . . no
C9 C32 3.481(5) . 1_554 no
C11 C5 3.550(6) . 4_454 no
C12 O30 3.388(5) . 1_454 no
C28 O9 3.024(4) . 4_555 no
C28 C33 3.593(4) . . no
C28 C35 3.268(5) . . no
C29 O9 3.043(4) . 4_555 no
C31 O29 3.207(5) . 3_566 no
C32 C9 3.481(5) . 1_556 no
C33 C8 3.026(4) . . no
C33 O8 3.003(4) . . no
C33 C28 3.593(4) . . no
C33 O8 3.241(4) . 3_565 no
C34 C4 3.568(4) . 3_665 no
C34 O28 3.254(4) . 4_554 no
C35 C28 3.268(5) . . no
C35 O28 3.304(5) . . no
C2 H32B 2.8100 . 4_554 no
C5 H11A 3.0500 . 4_655 no
C8 H33C 2.5500 . . no
C8 H27 3.0600 . 3_565 no
C8 H32A 2.8400 . 1_554 no
C8 H33A 3.0700 . . no
C9 H32A 2.6900 . 1_554 no
C11 H32C 3.1000 . 1_454 no
C12 H32C 2.8800 . 1_454 no
C28 H35C 3.0800 . . no
C28 H35A 3.0300 . . no
C28 H33B 2.9700 . . no
C28 H7 2.8100 . 4_555 no
C29 H7 3.0700 . 4_555 no
C32 H33A 3.0700 . 4_555 no
C33 H5 2.9200 . 1_455 no
C33 H32B 2.8400 . 4_554 no
C33 H27 3.0200 . . no
C34 H7 2.8600 . . no
C35 H34A 3.0500 . 3_665 no
H5 C33 2.9200 . 1_655 no
H5 H33B 2.5100 . 1_655 no
H5 H34B 2.3700 . . no
H5 H35B 2.3700 . . no
H7 O9 2.4100 . . no
H7 C34 2.8600 . . no
H7 O28 2.1300 . 4_554 no
H7 O30 2.6300 . 4_554 no
H7 C28 2.8100 . 4_554 no
H7 C29 3.0700 . 4_554 no
H11A O9 2.4700 . . no
H11A C5 3.0500 . 4_454 no
H11A H33A 2.5400 . 4_554 no
H11B H32C 2.5200 . 1_454 no
H12A H32C 2.3500 . 1_454 no
H12B H31B 2.2900 . 1_554 no
H12C O28 2.9200 . 1_454 no
H12C O30 2.7500 . 1_454 no
H27 O29 2.3900 . . no
H27 C33 3.0200 . . no
H27 H33B 2.4100 . . no
H27 O8 2.1100 . 3_565 no
H27 O10 2.7700 . 3_565 no
H27 C8 3.0600 . 3_565 no
H31A O29 2.5600 . . no
H31A O29 2.6500 . 3_566 no
H31B O29 2.7200 . . no
H31B H12B 2.2900 . 1_556 no
H32A O10 2.8900 . 1_556 no
H32A C8 2.8400 . 1_556 no
H32A C9 2.6900 . 1_556 no
H32B C2 2.8100 . 4_555 no
H32B C33 2.8400 . 4_555 no
H32B H33A 2.2300 . 4_555 no
H32C C11 3.1000 . 1_656 no
H32C C12 2.8800 . 1_656 no
H32C H11B 2.5200 . 1_656 no
H32C H12A 2.3500 . 1_656 no
H33A N7 2.8400 . . no
H33A C8 3.0700 . . no
H33A C32 3.0700 . 4_554 no
H33A H11A 2.5400 . 4_555 no
H33A H32B 2.2300 . 4_554 no
H33B N27 2.3400 . . no
H33B C28 2.9700 . . no
H33B H5 2.5100 . 1_455 no
H33B H27 2.4100 . . no
H33B O8 2.7500 . 3_565 no
H33C O8 2.2500 . . no
H33C N7 2.8400 . . no
H33C C8 2.5500 . . no
H33C H34B 2.5200 . 1_455 no
H34A N7 2.6500 . . no
H34A C35 3.0500 . 3_665 no
H34B H5 2.3700 . . no
H34B H33C 2.5200 . 1_655 no
H34C O28 2.5700 . 4_554 no
H35A O28 2.7600 . . no
H35A C28 3.0300 . . no
H35B O29 2.8400 . 1_655 no
H35B H5 2.3700 . . no
H35C N27 2.6500 . . no
H35C C28 3.0800 . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8800 2.4100 2.742(4) 103.00 . yes
N7 H7 O28 0.8800 2.1300 2.978(3) 162.00 4_554 yes
N27 H27 O29 0.8800 2.3900 2.739(4) 104.00 . yes
N27 H27 O8 0.8800 2.1100 2.867(4) 144.00 3_565 yes
C33 H33B N27 0.9800 2.3400 2.836(4) 111.00 . yes
C33 H33C O8 0.9800 2.2500 3.003(4) 133.00 . yes
C34 H34C O28 0.9800 2.5700 3.254(4) 127.00 4_554 yes

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.185

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;

data_mp
_database_code_depnum_ccdc_archive 'CCDC 795131'
#TrackingRef 'NEW-795131.CIF'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Diethyl N,N'-(1,3-(5-tert-buthyl-2-
methoxy)phenylene)dioxamalate

;
_chemical_name_common            
;Diethyl N,N'-(1,3-(5-tert-buthyl-2-
methoxy)phenylene)dioxamalate
;
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 N2 O7'
_chemical_formula_weight         394.42

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_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.9640(3)
_cell_length_b                   10.2180(3)
_cell_length_c                   10.5790(4)
_cell_angle_alpha                80.969(2)
_cell_angle_beta                 87.691(2)
_cell_angle_gamma                87.649(1)
_cell_volume                     1062.20(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker APEXII area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            11563
_diffrn_reflns_av_R_equivalents  0.1250
_diffrn_reflns_av_sigmaI/netI    0.0829
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.00
_reflns_number_total             3246
_reflns_number_gt                2455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 2008) and WINGX-2003 (Farrugia, 1999)'

_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^)+(0.1523P)^2^+0.1135P] 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       0.74(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3246
_refine_ls_number_parameters     311
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0815
_refine_ls_wR_factor_ref         0.2484
_refine_ls_wR_factor_gt          0.2147
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani -0.2155(3) 0.1086(2) 0.8365(2) 1.000 0.0827(9) . .
O9 O Uani -0.1972(3) 0.4110(2) 0.6348(3) 1.000 0.0947(11) . .
O10 O Uani -0.3439(3) 0.3462(3) 0.7980(3) 1.000 0.0939(10) . .
O18 O Uani 0.4200(3) -0.1882(2) 0.4480(2) 1.000 0.0769(9) . .
O19 O Uani 0.4598(3) 0.1140(3) 0.2484(2) 1.000 0.0876(10) . .
O20 O Uani 0.5636(2) -0.0842(2) 0.24183(18) 1.000 0.0681(8) . .
O23 O Uani 0.1423(2) 0.21350(17) 0.50130(17) 1.000 0.0583(7) . .
N7 N Uani -0.0629(3) 0.1813(2) 0.6762(2) 1.000 0.0570(8) . .
N17 N Uani 0.3077(3) 0.0104(2) 0.4509(2) 1.000 0.0579(8) . .
C1 C Uani 0.0222(3) 0.0707(3) 0.6655(2) 1.000 0.0488(8) . .
C2 C Uani 0.1268(3) 0.0897(2) 0.5746(2) 1.000 0.0483(8) . .
C3 C Uani 0.2104(3) -0.0168(3) 0.5513(2) 1.000 0.0495(9) . .
C4 C Uani 0.1940(3) -0.1414(3) 0.6242(2) 1.000 0.0527(9) . .
C5 C Uani 0.0929(3) -0.1608(2) 0.7190(2) 1.000 0.0526(9) . .
C6 C Uani 0.0064(3) -0.0544(2) 0.7384(2) 1.000 0.0519(9) . .
C8 C Uani -0.1716(3) 0.1931(3) 0.7537(3) 1.000 0.0569(10) . .
C9 C Uani -0.2389(3) 0.3305(3) 0.7220(3) 1.000 0.0674(11) . .
C11A C Uani -0.3995(12) 0.4826(5) 0.7796(11) 0.538(17) 0.090(4) . .
C12A C Uani -0.5021(10) 0.4883(12) 0.6734(12) 0.538(17) 0.131(5) . .
C18 C Uani 0.3991(3) -0.0727(3) 0.4058(3) 1.000 0.0552(10) . .
C19 C Uani 0.4780(3) -0.0020(3) 0.2882(3) 1.000 0.0606(10) . .
C21 C Uani 0.6434(4) -0.0308(4) 0.1277(3) 1.000 0.0774(13) . .
C22 C Uani 0.6942(7) -0.1445(5) 0.0695(4) 1.000 0.132(2) . .
C24 C Uani 0.2292(4) 0.2968(3) 0.5572(3) 1.000 0.0754(11) . .
C25A C Uani 0.0821(6) -0.2993(3) 0.8004(5) 0.646(14) 0.051(3) . .
C26B C Uani 0.2066(9) -0.3221(7) 0.8841(8) 0.646(14) 0.102(3) . .
C27A C Uani 0.0853(12) -0.4063(8) 0.7124(9) 0.646(14) 0.106(4) . .
C28A C Uani -0.0427(13) -0.3049(8) 0.8918(14) 0.646(14) 0.177(7) . .
C28B C Uani -0.0727(8) -0.3320(12) 0.8094(13) 0.354(14) 0.080(4) . .
C27B C Uani 0.147(3) -0.4036(14) 0.754(2) 0.354(14) 0.144(12) . .
C12B C Uani -0.406(2) 0.5488(19) 0.841(3) 0.462(17) 0.239(13) . .
C25B C Uani 0.0739(7) -0.2904(7) 0.8135(9) 0.354(14) 0.100(10) . .
C11B C Uani -0.4458(14) 0.4493(13) 0.755(2) 0.462(17) 0.129(8) . .
C26A C Uani 0.107(2) -0.2822(13) 0.9398(7) 0.354(14) 0.107(7) . .
H7 H Uiso -0.04248 0.25258 0.62552 1.000 0.0683 . .
H11A H Uiso -0.44325 0.50312 0.85808 0.538(17) 0.1079 . .
H6 H Uiso -0.06252 -0.06687 0.80052 1.000 0.0623 . .
H21A H Uiso 0.58808 0.02807 0.06837 1.000 0.0925 . .
H21B H Uiso 0.71731 0.01854 0.15088 1.000 0.0925 . .
H11B H Uiso -0.32925 0.54518 0.75349 0.538(17) 0.1079 . .
H12A H Uiso -0.54576 0.57455 0.65939 0.538(17) 0.1970 . .
H12B H Uiso -0.56795 0.42242 0.69908 0.538(17) 0.1970 . .
H12C H Uiso -0.45640 0.47131 0.59568 0.538(17) 0.1970 . .
H17 H Uiso 0.30862 0.09140 0.41339 1.000 0.0694 . .
H24C H Uiso 0.23594 0.38072 0.50236 1.000 0.1133 . .
H26D H Uiso 0.20718 -0.25501 0.93821 0.646(14) 0.1535 . .
H26E H Uiso 0.20345 -0.40788 0.93609 0.646(14) 0.1535 . .
H26F H Uiso 0.28654 -0.31757 0.83008 0.646(14) 0.1535 . .
H27A H Uiso 0.00846 -0.39328 0.65928 0.646(14) 0.1586 . .
H27B H Uiso 0.08342 -0.49246 0.76368 0.646(14) 0.1586 . .
H27C H Uiso 0.16593 -0.39961 0.65929 0.646(14) 0.1586 . .
H28A H Uiso -0.12227 -0.28830 0.84271 0.646(14) 0.2651 . .
H28B H Uiso -0.03755 -0.23871 0.94643 0.646(14) 0.2651 . .
H28C H Uiso -0.04592 -0.39100 0.94310 0.646(14) 0.2651 . .
H22A H Uiso 0.74754 -0.11396 -0.00619 1.000 0.1988 . .
H22B H Uiso 0.61992 -0.19222 0.04702 1.000 0.1988 . .
H22C H Uiso 0.74836 -0.20187 0.12930 1.000 0.1988 . .
H24A H Uiso 0.31685 0.25458 0.56668 1.000 0.1133 . .
H24B H Uiso 0.19258 0.31046 0.63960 1.000 0.1133 . .
H4 H Uiso 0.25112 -0.21208 0.60926 1.000 0.0633 . .
H11C H Uiso -0.53662 0.41928 0.77376 0.462(17) 0.1548 . .
H11D H Uiso -0.43481 0.48401 0.66443 0.462(17) 0.1548 . .
H12D H Uiso -0.45754 0.63038 0.81974 0.462(17) 0.3608 . .
H12E H Uiso -0.42434 0.51265 0.92916 0.462(17) 0.3608 . .
H12F H Uiso -0.31220 0.56551 0.82799 0.462(17) 0.3608 . .
H26A H Uiso 0.05854 -0.20787 0.96752 0.354(14) 0.1595 . .
H26B H Uiso 0.08220 -0.36220 0.99477 0.354(14) 0.1595 . .
H26C H Uiso 0.20151 -0.27098 0.94334 0.354(14) 0.1595 . .
H27D H Uiso 0.24185 -0.39381 0.75445 0.354(14) 0.2140 . .
H27E H Uiso 0.11910 -0.40018 0.66772 0.354(14) 0.2140 . .
H27F H Uiso 0.12358 -0.48728 0.80349 0.354(14) 0.2140 . .
H28D H Uiso -0.08313 -0.41759 0.86036 0.354(14) 0.1209 . .
H28E H Uiso -0.09423 -0.33605 0.72249 0.354(14) 0.1209 . .
H28F H Uiso -0.13194 -0.26823 0.84278 0.354(14) 0.1209 . .

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
O8 0.0949(19) 0.0669(14) 0.0750(14) 0.0115(11) 0.0296(13) 0.0147(12)
O9 0.096(2) 0.0519(14) 0.123(2) 0.0146(13) 0.0282(16) 0.0152(12)
O10 0.095(2) 0.0885(18) 0.0898(16) -0.0049(13) 0.0236(15) 0.0347(15)
O18 0.0802(17) 0.0623(14) 0.0813(14) 0.0014(11) 0.0224(12) 0.0082(11)
O19 0.111(2) 0.0667(16) 0.0791(15) -0.0009(12) 0.0318(14) -0.0070(14)
O20 0.0626(14) 0.0789(15) 0.0598(12) -0.0063(10) 0.0158(10) 0.0001(11)
O23 0.0690(14) 0.0415(11) 0.0586(11) 0.0091(8) 0.0026(9) -0.0022(9)
N7 0.0630(16) 0.0409(13) 0.0620(13) 0.0034(10) 0.0090(12) 0.0026(11)
N17 0.0665(16) 0.0492(14) 0.0549(13) -0.0013(10) 0.0110(12) -0.0055(11)
C1 0.0524(16) 0.0414(14) 0.0506(13) -0.0022(10) 0.0003(12) -0.0001(12)
C2 0.0558(16) 0.0384(14) 0.0481(14) 0.0015(10) -0.0009(12) -0.0047(11)
C3 0.0537(17) 0.0462(15) 0.0474(13) -0.0037(10) 0.0022(12) -0.0052(12)
C4 0.0589(18) 0.0425(14) 0.0546(15) -0.0030(12) 0.0030(13) 0.0023(12)
C5 0.0607(18) 0.0401(15) 0.0535(14) 0.0014(11) 0.0063(13) -0.0020(12)
C6 0.0568(17) 0.0417(15) 0.0537(14) 0.0008(11) 0.0072(12) 0.0005(12)
C8 0.0639(19) 0.0486(16) 0.0561(15) -0.0047(12) 0.0043(14) 0.0023(13)
C9 0.069(2) 0.0563(18) 0.0746(19) -0.0082(14) 0.0064(16) 0.0098(15)
C11A 0.076(7) 0.079(8) 0.118(7) -0.038(5) 0.008(5) 0.032(5)
C12A 0.081(7) 0.103(7) 0.201(12) 0.000(7) -0.017(7) 0.023(5)
C18 0.0547(17) 0.0562(18) 0.0545(15) -0.0086(13) 0.0016(13) -0.0032(13)
C19 0.0638(19) 0.066(2) 0.0520(15) -0.0083(14) 0.0007(14) -0.0080(15)
C21 0.074(2) 0.099(3) 0.0565(17) -0.0075(16) 0.0194(15) -0.0098(19)
C22 0.177(6) 0.127(4) 0.076(2) 0.009(2) 0.055(3) 0.047(4)
C24 0.081(2) 0.0452(16) 0.096(2) 0.0035(15) -0.0002(18) -0.0138(15)
C25A 0.061(5) 0.037(4) 0.048(4) 0.007(3) 0.015(4) -0.006(3)
C26B 0.132(7) 0.078(4) 0.085(5) 0.031(3) -0.023(5) -0.011(4)
C27A 0.168(10) 0.043(4) 0.104(5) 0.005(3) -0.027(6) -0.024(5)
C28A 0.203(14) 0.073(5) 0.209(13) 0.060(7) 0.170(12) 0.050(7)
C28B 0.097(9) 0.056(6) 0.079(7) 0.015(5) 0.029(6) -0.025(6)
C27B 0.22(3) 0.039(7) 0.151(16) 0.011(8) 0.126(19) 0.031(10)
C12B 0.24(2) 0.118(13) 0.38(3) -0.106(19) -0.06(2) 0.060(13)
C25B 0.12(2) 0.053(11) 0.119(19) -0.003(10) -0.001(16) 0.030(12)
C11B 0.083(12) 0.107(10) 0.188(18) 0.004(11) -0.013(10) 0.021(8)
C26A 0.139(17) 0.087(9) 0.082(8) 0.042(6) -0.027(9) -0.048(10)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.211(4) . . yes
O9 C9 1.208(4) . . yes
O10 C9 1.314(4) . . yes
O10 C11A 1.465(7) . . yes
O10 C11B 1.465(15) . . yes
O18 C18 1.207(4) . . yes
O19 C19 1.203(4) . . yes
O20 C19 1.308(4) . . yes
O20 C21 1.463(4) . . yes
O23 C2 1.387(3) . . yes
O23 C24 1.444(4) . . yes
N7 C1 1.401(4) . . yes
N7 C8 1.345(4) . . yes
N17 C3 1.411(4) . . yes
N17 C18 1.344(4) . . yes
N7 H7 0.8600 . . no
N17 H17 0.8600 . . no
C1 C2 1.388(4) . . no
C1 C6 1.397(4) . . no
C2 C3 1.390(4) . . no
C3 C4 1.393(4) . . no
C4 C5 1.390(4) . . no
C5 C25B 1.542(8) . . no
C5 C25A 1.542(4) . . no
C5 C6 1.395(3) . . no
C8 C9 1.525(4) . . no
C11A C12A 1.542(16) . . no
C11B C12B 1.54(3) . . no
C18 C19 1.541(4) . . no
C21 C22 1.462(7) . . no
C25A C28A 1.542(15) . . no
C25A C26B 1.542(10) . . no
C25A C27A 1.542(10) . . no
C25B C28B 1.542(11) . . no
C25B C26A 1.405(13) . . no
C25B C27B 1.55(2) . . no
C4 H4 0.9300 . . no
C6 H6 0.9300 . . no
C11A H11A 0.9700 . . no
C11A H11B 0.9700 . . no
C11B H11D 0.9700 . . no
C11B H11C 0.9700 . . no
C12A H12B 0.9600 . . no
C12A H12A 0.9600 . . no
C12A H12C 0.9600 . . no
C12B H12D 0.9600 . . no
C12B H12F 0.9600 . . no
C12B H12E 0.9600 . . no
C21 H21B 0.9700 . . no
C21 H21A 0.9700 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C24 H24C 0.9600 . . no
C24 H24B 0.9600 . . no
C24 H24A 0.9600 . . no
C26A H26C 0.9600 . . no
C26A H26B 0.9600 . . no
C26A H26A 0.9600 . . no
C26B H26D 0.9600 . . no
C26B H26F 0.9600 . . no
C26B H26E 0.9600 . . no
C27A H27B 0.9600 . . no
C27A H27C 0.9600 . . no
C27A H27A 0.9600 . . no
C27B H27D 0.9500 . . no
C27B H27E 0.9600 . . no
C27B H27F 0.9600 . . no
C28A H28B 0.9600 . . no
C28A H28C 0.9600 . . no
C28A H28A 0.9600 . . no
C28B H28D 0.9600 . . no
C28B H28E 0.9600 . . no
C28B H28F 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11A 112.8(5) . . . yes
C9 O10 C11B 118.6(8) . . . yes
C19 O20 C21 116.9(3) . . . yes
C2 O23 C24 113.3(2) . . . yes
C1 N7 C8 129.9(2) . . . yes
C3 N17 C18 129.0(2) . . . yes
C8 N7 H7 115.00 . . . no
C1 N7 H7 115.00 . . . no
C3 N17 H17 115.00 . . . no
C18 N17 H17 116.00 . . . no
N7 C1 C6 124.2(2) . . . yes
C2 C1 C6 119.5(3) . . . no
N7 C1 C2 116.3(2) . . . yes
O23 C2 C1 119.7(2) . . . yes
O23 C2 C3 120.0(2) . . . yes
C1 C2 C3 120.1(2) . . . no
N17 C3 C2 116.0(2) . . . yes
N17 C3 C4 124.1(3) . . . yes
C2 C3 C4 120.0(2) . . . no
C3 C4 C5 120.5(3) . . . no
C4 C5 C6 119.1(2) . . . no
C4 C5 C25A 118.5(3) . . . no
C6 C5 C25B 116.0(3) . . . no
C4 C5 C25B 124.8(4) . . . no
C6 C5 C25A 122.4(3) . . . no
C1 C6 C5 120.7(2) . . . no
O8 C8 C9 122.5(3) . . . yes
N7 C8 C9 110.6(3) . . . yes
O8 C8 N7 126.9(3) . . . yes
O9 C9 O10 126.5(3) . . . yes
O9 C9 C8 121.4(3) . . . yes
O10 C9 C8 112.1(3) . . . yes
O10 C11A C12A 105.2(7) . . . yes
O10 C11B C12B 96.7(13) . . . yes
N17 C18 C19 111.1(3) . . . yes
O18 C18 N17 126.7(3) . . . yes
O18 C18 C19 122.2(3) . . . yes
O19 C19 O20 126.8(3) . . . yes
O19 C19 C18 122.2(3) . . . yes
O20 C19 C18 111.0(3) . . . yes
O20 C21 C22 106.5(3) . . . yes
C5 C25A C28A 111.0(5) . . . no
C27A C25A C28A 113.1(6) . . . no
C26B C25A C27A 108.4(6) . . . no
C5 C25A C26B 107.1(4) . . . no
C5 C25A C27A 109.9(5) . . . no
C26B C25A C28A 107.2(7) . . . no
C26A C25B C28B 110.4(11) . . . no
C27B C25B C28B 99.7(12) . . . no
C26A C25B C27B 115.4(12) . . . no
C5 C25B C26A 114.0(7) . . . no
C5 C25B C27B 107.5(9) . . . no
C5 C25B C28B 108.7(7) . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
O10 C11A H11A 111.00 . . . no
O10 C11A H11B 111.00 . . . no
C12A C11A H11A 111.00 . . . no
C12A C11A H11B 111.00 . . . no
H11A C11A H11B 109.00 . . . no
H11C C11B H11D 110.00 . . . no
O10 C11B H11D 112.00 . . . no
C12B C11B H11C 113.00 . . . no
O10 C11B H11C 112.00 . . . no
C12B C11B H11D 112.00 . . . no
C11A C12A H12B 109.00 . . . no
C11A C12A H12C 109.00 . . . no
C11A C12A H12A 109.00 . . . no
H12A C12A H12C 110.00 . . . no
H12B C12A H12C 109.00 . . . no
H12A C12A H12B 109.00 . . . no
C11B C12B H12D 109.00 . . . no
C11B C12B H12E 109.00 . . . no
H12E C12B H12F 110.00 . . . no
C11B C12B H12F 110.00 . . . no
H12D C12B H12E 109.00 . . . no
H12D C12B H12F 110.00 . . . no
O20 C21 H21B 110.00 . . . no
C22 C21 H21A 110.00 . . . no
C22 C21 H21B 110.00 . . . no
O20 C21 H21A 110.00 . . . no
H21A C21 H21B 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 109.00 . . . no
H22A C22 H22C 110.00 . . . no
H22B C22 H22C 110.00 . . . no
H22A C22 H22B 109.00 . . . no
C21 C22 H22A 109.00 . . . no
H24A C24 H24C 109.00 . . . no
H24B C24 H24C 109.00 . . . no
O23 C24 H24A 109.00 . . . no
O23 C24 H24B 109.00 . . . no
O23 C24 H24C 109.00 . . . no
H24A C24 H24B 110.00 . . . no
H26A C26A H26B 109.00 . . . no
H26A C26A H26C 110.00 . . . no
C25B C26A H26C 110.00 . . . no
C25B C26A H26A 109.00 . . . no
C25B C26A H26B 109.00 . . . no
H26B C26A H26C 110.00 . . . no
C25A C26B H26D 109.00 . . . no
C25A C26B H26E 109.00 . . . no
H26D C26B H26F 109.00 . . . no
H26E C26B H26F 110.00 . . . no
H26D C26B H26E 109.00 . . . no
C25A C26B H26F 109.00 . . . no
C25A C27A H27B 109.00 . . . no
C25A C27A H27A 109.00 . . . no
H27A C27A H27C 109.00 . . . no
C25A C27A H27C 109.00 . . . no
H27A C27A H27B 109.00 . . . no
H27B C27A H27C 110.00 . . . no
C25B C27B H27D 110.00 . . . no
C25B C27B H27E 109.00 . . . no
H27D C27B H27E 110.00 . . . no
H27D C27B H27F 110.00 . . . no
C25B C27B H27F 109.00 . . . no
H27E C27B H27F 109.00 . . . no
C25A C28A H28B 109.00 . . . no
C25A C28A H28C 109.00 . . . no
C25A C28A H28A 109.00 . . . no
H28A C28A H28C 110.00 . . . no
H28B C28A H28C 110.00 . . . no
H28A C28A H28B 109.00 . . . no
C25B C28B H28D 109.00 . . . no
C25B C28B H28E 109.00 . . . no
C25B C28B H28F 109.00 . . . no
H28D C28B H28E 109.00 . . . no
H28D C28B H28F 109.00 . . . no
H28E C28B H28F 109.00 . . . no

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
C11A O10 C9 O9 -8.3(7) . . . . no
C11A O10 C9 C8 172.8(5) . . . . no
C9 O10 C11A C12A 88.6(8) . . . . no
C19 O20 C21 C22 -160.9(3) . . . . no
C21 O20 C19 C18 178.6(2) . . . . no
C21 O20 C19 O19 -1.7(5) . . . . no
C24 O23 C2 C1 91.1(3) . . . . no
C24 O23 C2 C3 -93.1(3) . . . . no
C8 N7 C1 C2 179.5(3) . . . . no
C8 N7 C1 C6 0.4(5) . . . . no
C1 N7 C8 O8 3.6(5) . . . . no
C1 N7 C8 C9 -175.0(3) . . . . no
C3 N17 C18 O18 -4.0(5) . . . . no
C18 N17 C3 C4 0.6(5) . . . . no
C18 N17 C3 C2 -178.6(3) . . . . no
C3 N17 C18 C19 175.7(3) . . . . no
C6 C1 C2 O23 179.5(2) . . . . no
N7 C1 C2 O23 0.3(4) . . . . no
C2 C1 C6 C5 -1.3(4) . . . . no
N7 C1 C2 C3 -175.5(2) . . . . no
N7 C1 C6 C5 177.8(2) . . . . no
C6 C1 C2 C3 3.7(4) . . . . no
C1 C2 C3 C4 -3.6(4) . . . . no
O23 C2 C3 C4 -179.4(2) . . . . no
C1 C2 C3 N17 175.6(2) . . . . no
O23 C2 C3 N17 -0.2(4) . . . . no
C2 C3 C4 C5 1.1(4) . . . . no
N17 C3 C4 C5 -178.0(3) . . . . no
C3 C4 C5 C6 1.3(4) . . . . no
C3 C4 C5 C25A -177.8(3) . . . . no
C6 C5 C25A C27A 131.7(6) . . . . no
C6 C5 C25A C26B -110.8(5) . . . . no
C4 C5 C6 C1 -1.2(4) . . . . no
C4 C5 C25A C28A -175.0(6) . . . . no
C4 C5 C25A C27A -49.2(7) . . . . no
C4 C5 C25A C26B 68.3(5) . . . . no
C6 C5 C25A C28A 5.9(7) . . . . no
C25A C5 C6 C1 177.9(3) . . . . no
N7 C8 C9 O10 -178.6(3) . . . . no
N7 C8 C9 O9 2.3(4) . . . . no
O8 C8 C9 O9 -176.3(3) . . . . no
O8 C8 C9 O10 2.8(4) . . . . no
O18 C18 C19 O19 -177.8(3) . . . . no
O18 C18 C19 O20 1.9(4) . . . . no
N17 C18 C19 O19 2.5(4) . . . . no
N17 C18 C19 O20 -177.8(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 O10 2.678(4) . . no
O8 C6 2.966(4) . . no
O8 C22 3.404(5) . 1_456 no
O8 C19 3.276(4) . 2_556 no
O8 C26A 3.405(12) . 2_557 no
O8 C18 3.283(4) . 2_556 no
O9 C12A 3.134(11) . . no
O9 C12B 3.38(3) . . no
O9 N7 2.638(3) . . no
O9 C24 3.348(4) . 2_566 no
O10 O8 2.678(4) . . no
O18 C4 2.937(4) . . no
O18 C8 3.339(4) . 2_556 no
O18 O20 2.661(3) . . no
O18 C9 3.147(4) . 2_556 no
O19 N17 2.677(3) . . no
O20 O18 2.661(3) . . no
O23 N17 2.702(3) . . no
O23 N7 2.697(3) . . no
O23 C28B 3.408(13) . 2_556 no
O8 H22A 2.6300 . 1_456 no
O8 H6 2.3700 . . no
O9 H12C 2.6600 . . no
O9 H7 2.2000 . . no
O9 H11B 2.3300 . . no
O9 H11D 2.4800 . . no
O9 H24C 2.4100 . 2_566 no
O18 H4 2.3400 . . no
O18 H24A 2.6900 . 2_656 no
O19 H21A 2.5000 . . no
O19 H21B 2.9100 . . no
O19 H12D 2.6000 . 2_566 no
O19 H17 2.2500 . . no
O20 H24A 2.7300 . 2_656 no
O23 H17 2.2900 . . no
O23 H27A 2.7400 . 2_556 no
O23 H7 2.2800 . . no
O23 H28E 2.5500 . 2_556 no
N7 O9 2.638(3) . . no
N7 O23 2.697(3) . . no
N7 C24 3.312(5) . . no
N17 C24 3.349(4) . . no
N17 O19 2.677(3) . . no
N17 O23 2.702(3) . . no
N7 H24B 2.9000 . . no
C1 C3 3.445(4) . 2_556 no
C3 C1 3.445(4) . 2_556 no
C4 O18 2.937(4) . . no
C6 O8 2.966(4) . . no
C8 C18 3.269(4) . 2_556 no
C8 C26A 3.592(10) . 2_557 no
C8 O18 3.339(4) . 2_556 no
C9 C18 3.599(4) . 2_556 no
C9 O18 3.147(4) . 2_556 no
C12A O9 3.134(11) . . no
C12B O9 3.38(3) . . no
C18 C9 3.599(4) . 2_556 no
C18 C18 3.424(4) . 2_656 no
C18 O8 3.283(4) . 2_556 no
C18 C8 3.269(4) . 2_556 no
C19 O8 3.276(4) . 2_556 no
C22 O8 3.404(5) . 1_654 no
C24 N17 3.349(4) . . no
C24 N7 3.312(5) . . no
C24 O9 3.348(4) . 2_566 no
C26A C8 3.592(10) . 2_557 no
C26A O8 3.405(12) . 2_557 no
C28B O23 3.408(13) . 2_556 no
C1 H24B 3.0100 . . no
C3 H24A 3.0400 . . no
C4 H21B 3.0400 . 2_656 no
C4 H27D 2.7600 . . no
C4 H27C 2.6300 . . no
C4 H26F 2.7600 . . no
C4 H27E 2.7400 . . no
C5 H21B 2.9400 . 2_656 no
C6 H26A 2.7300 . . no
C6 H21B 3.0900 . 2_656 no
C6 H28F 2.6900 . . no
C6 H28A 2.8100 . . no
C6 H28B 2.7000 . . no
C8 H6 2.8100 . . no
C9 H12F 2.8600 . . no
C9 H12C 2.8200 . . no
C12A H12C 2.8600 . 2_466 no
C12A H27D 2.9300 . 1_465 no
C12B H12E 2.9100 . 2_467 no
C18 H4 2.7900 . . no
C24 H17 2.8500 . . no
C24 H7 2.8100 . . no
C24 H12B 3.0100 . 1_655 no
C26A H6 2.9600 . . no
C26B H4 2.9700 . . no
C27A H4 2.7000 . . no
C27B H4 2.5200 . . no
C28A H6 2.4800 . . no
C28A H22A 3.0800 . 1_456 no
C28B H11B 3.0100 . 1_545 no
C28B H6 2.7000 . . no
H4 C18 2.7900 . . no
H4 C26B 2.9700 . . no
H4 H27E 2.3600 . . no
H4 H27C 2.1100 . . no
H4 C27B 2.5200 . . no
H4 H27D 2.2200 . . no
H4 O18 2.3400 . . no
H4 H26F 2.4500 . . no
H4 C27A 2.7000 . . no
H6 C8 2.8100 . . no
H6 O8 2.3700 . . no
H6 H28F 2.1700 . . no
H6 C28A 2.4800 . . no
H6 H28A 2.3300 . . no
H6 H28B 2.1600 . . no
H6 C26A 2.9600 . . no
H6 C28B 2.7000 . . no
H6 H26A 2.4300 . . no
H7 C24 2.8100 . . no
H7 H24B 2.4500 . . no
H7 O23 2.2800 . . no
H7 O9 2.2000 . . no
H11B C28B 3.0100 . 1_565 no
H11B O9 2.3300 . . no
H11D O9 2.4800 . . no
H12A H27D 2.3400 . 1_465 no
H12B C24 3.0100 . 1_455 no
H12C O9 2.6600 . . no
H12C C9 2.8200 . . no
H12C H12C 2.2200 . 2_466 no
H12C C12A 2.8600 . 2_466 no
H12D O19 2.6000 . 2_566 no
H12E C12B 2.9100 . 2_467 no
H12E H12E 2.0800 . 2_467 no
H12F C9 2.8600 . . no
H17 O19 2.2500 . . no
H17 H24A 2.5100 . . no
H17 O23 2.2900 . . no
H17 C24 2.8500 . . no
H21A O19 2.5000 . . no
H21A H21A 2.4600 . 2_655 no
H21B C4 3.0400 . 2_656 no
H21B O19 2.9100 . . no
H21B H26D 2.5800 . 2_656 no
H21B C5 2.9400 . 2_656 no
H21B C6 3.0900 . 2_656 no
H22A C28A 3.0800 . 1_654 no
H22A O8 2.6300 . 1_654 no
H22A H28B 2.5200 . 1_654 no
H24A C3 3.0400 . . no
H24A H17 2.5100 . . no
H24A O20 2.7300 . 2_656 no
H24A O18 2.6900 . 2_656 no
H24B C1 3.0100 . . no
H24B N7 2.9000 . . no
H24B H7 2.4500 . . no
H24C O9 2.4100 . 2_566 no
H26A H6 2.4300 . . no
H26A C6 2.7300 . . no
H26A H28F 2.5100 . . no
H26B H28D 2.3600 . . no
H26B H28D 2.5200 . 2_547 no
H26B H27F 2.5700 . . no
H26C H27D 2.5300 . . no
H26D H28B 2.4400 . . no
H26D H21B 2.5800 . 2_656 no
H26E H28C 2.4800 . . no
H26E H27B 2.5000 . . no
H26F H4 2.4500 . . no
H26F C4 2.7600 . . no
H26F H27C 2.4800 . . no
H27A O23 2.7400 . 2_556 no
H27B H26E 2.5000 . . no
H27B H28C 2.5800 . . no
H27C H4 2.1100 . . no
H27C H26F 2.4800 . . no
H27C C4 2.6300 . . no
H27D H4 2.2200 . . no
H27D C12A 2.9300 . 1_645 no
H27D C4 2.7600 . . no
H27D H12A 2.3400 . 1_645 no
H27D H26C 2.5300 . . no
H27E C4 2.7400 . . no
H27E H4 2.3600 . . no
H27E H28E 2.2800 . . no
H27F H26B 2.5700 . . no
H27F H28D 2.2400 . . no
H28A C6 2.8100 . . no
H28A H6 2.3300 . . no
H28B C6 2.7000 . . no
H28B H6 2.1600 . . no
H28B H22A 2.5200 . 1_456 no
H28B H26D 2.4400 . . no
H28C H26E 2.4800 . . no
H28C H27B 2.5800 . . no
H28C H28C 2.5200 . 2_547 no
H28D H26B 2.3600 . . no
H28D H27F 2.2400 . . no
H28D H26B 2.5200 . 2_547 no
H28E H27E 2.2800 . . no
H28E O23 2.5500 . 2_556 no
H28F C6 2.6900 . . no
H28F H6 2.1700 . . no
H28F H26A 2.5100 . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.2000 2.638(3) 111.00 . yes
N7 H7 O23 0.8600 2.2800 2.697(3) 110.00 . yes
N17 H17 O19 0.8600 2.2500 2.677(3) 111.00 . yes
N17 H17 O23 0.8600 2.2900 2.702(3) 110.00 . yes
C4 H4 O18 0.9300 2.3400 2.937(4) 122.00 . yes
C6 H6 O8 0.9300 2.3700 2.966(4) 122.00 . yes
C24 H24C O9 0.9600 2.4100 3.348(4) 167.00 2_566 yes

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        24.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.153

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;

data_sauleinx
_database_code_depnum_ccdc_archive 'CCDC 795133'
#TrackingRef 'saulo5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Diethyl N,N'-[1,3-(2-methyl)phenylene]dioxamalate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N2 O6'
_chemical_formula_weight         322.31

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.2302(12)
_cell_length_b                   23.218(3)
_cell_length_c                   8.1795(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.665(2)
_cell_angle_gamma                90.00
_cell_volume                     1557.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker APEXII area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            14126
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2745
_reflns_number_gt                2560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 2008) and WINGX-2003 (Farrugia, 1999)'

_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^)+(0.0448P)^2^+0.9181P] 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         2745
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1254
_refine_ls_wR_factor_gt          0.1230
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani 0.69815(18) -0.09458(7) 0.80121(19) 1.000 0.0425(5) . .
O9 O Uani 1.1104(2) -0.12673(9) 0.8756(3) 1.000 0.0640(7) . .
O10 O Uani 0.89805(18) -0.16020(6) 1.00063(18) 1.000 0.0414(5) . .
O18 O Uani 0.82441(18) 0.14505(7) 0.5110(2) 1.000 0.0446(5) . .
O19 O Uani 0.4171(2) 0.18828(7) 0.4802(2) 1.000 0.0538(6) . .
O20 O Uani 0.64459(19) 0.23971(6) 0.5454(2) 1.000 0.0465(5) . .
N7 N Uani 0.9071(2) -0.07655(8) 0.6428(2) 1.000 0.0393(6) . .
N17 N Uani 0.5963(2) 0.09307(7) 0.4393(2) 1.000 0.0384(6) . .
C1 C Uani 0.8203(2) -0.04406(9) 0.5152(3) 1.000 0.0339(6) . .
C2 C Uani 0.7510(2) 0.00928(9) 0.5496(3) 1.000 0.0321(6) . .
C3 C Uani 0.6726(2) 0.03856(9) 0.4154(3) 1.000 0.0336(6) . .
C4 C Uani 0.6634(3) 0.01609(10) 0.2584(3) 1.000 0.0414(7) . .
C5 C Uani 0.7325(3) -0.03652(10) 0.2289(3) 1.000 0.0452(8) . .
C6 C Uani 0.8109(3) -0.06676(10) 0.3577(3) 1.000 0.0421(7) . .
C8 C Uani 0.8409(3) -0.09880(9) 0.7725(3) 1.000 0.0336(7) . .
C9 C Uani 0.9672(3) -0.13014(9) 0.8889(3) 1.000 0.0379(7) . .
C11 C Uani 1.0101(3) -0.19278(10) 1.1145(3) 1.000 0.0456(8) . .
C12 C Uani 0.9144(4) -0.23229(13) 1.2104(4) 1.000 0.0701(11) . .
C18 C Uani 0.6776(3) 0.14109(9) 0.4837(2) 1.000 0.0328(6) . .
C19 C Uani 0.5622(3) 0.19267(9) 0.5014(3) 1.000 0.0363(7) . .
C21 C Uani 0.5501(3) 0.29192(10) 0.5730(3) 1.000 0.0502(8) . .
C22 C Uani 0.5214(3) 0.32609(11) 0.4200(3) 1.000 0.0564(9) . .
C23 C Uani 0.7617(3) 0.03410(10) 0.7197(3) 1.000 0.0427(7) . .
H4 H Uiso 0.61023 0.03661 0.17228 1.000 0.0498 . .
H5 H Uiso 0.72654 -0.05156 0.12319 1.000 0.0542 . .
H6 H Uiso 0.85736 -0.10240 0.33888 1.000 0.0505 . .
H7 H Uiso 1.00949 -0.08218 0.63534 1.000 0.0471 . .
H11A H Uiso 1.07230 -0.16655 1.18754 1.000 0.0547 . .
H11B H Uiso 1.08573 -0.21457 1.05371 1.000 0.0547 . .
H12A H Uiso 0.98676 -0.25385 1.28528 1.000 0.1051 . .
H12B H Uiso 0.85375 -0.25830 1.13736 1.000 0.1051 . .
H12C H Uiso 0.84041 -0.21044 1.27079 1.000 0.1051 . .
H17 H Uiso 0.49179 0.09496 0.42411 1.000 0.0460 . .
H21A H Uiso 0.60850 0.31529 0.65673 1.000 0.0602 . .
H21B H Uiso 0.44617 0.28122 0.61231 1.000 0.0602 . .
H22A H Uiso 0.45931 0.35988 0.44139 1.000 0.0847 . .
H22B H Uiso 0.46211 0.30319 0.33753 1.000 0.0847 . .
H22C H Uiso 0.62410 0.33728 0.38203 1.000 0.0847 . .
H23A H Uiso 0.81846 0.07024 0.72042 1.000 0.0640 . .
H23B H Uiso 0.81971 0.00791 0.79415 1.000 0.0640 . .
H23C H Uiso 0.65386 0.04004 0.75314 1.000 0.0640 . .

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
O8 0.0323(8) 0.0496(10) 0.0458(9) 0.0108(7) 0.0047(7) 0.0050(7)
O9 0.0353(10) 0.0767(13) 0.0792(13) 0.0347(11) 0.0000(9) 0.0023(9)
O10 0.0404(9) 0.0419(9) 0.0414(9) 0.0098(7) 0.0011(7) 0.0053(7)
O18 0.0328(9) 0.0398(9) 0.0605(10) -0.0024(8) -0.0005(7) -0.0002(7)
O19 0.0398(10) 0.0446(10) 0.0763(12) -0.0074(9) 0.0009(8) 0.0088(8)
O20 0.0490(9) 0.0308(8) 0.0602(10) -0.0027(7) 0.0085(8) -0.0002(7)
N7 0.0297(9) 0.0388(10) 0.0501(11) 0.0135(8) 0.0079(8) 0.0080(8)
N17 0.0278(9) 0.0320(10) 0.0542(11) 0.0031(8) -0.0031(8) 0.0041(7)
C1 0.0291(10) 0.0316(11) 0.0419(12) 0.0073(9) 0.0077(9) -0.0004(9)
C2 0.0277(10) 0.0300(11) 0.0389(11) 0.0019(9) 0.0050(8) -0.0023(8)
C3 0.0270(10) 0.0278(10) 0.0458(12) 0.0029(9) 0.0018(9) -0.0023(8)
C4 0.0402(12) 0.0430(13) 0.0401(12) 0.0044(10) -0.0029(10) -0.0011(10)
C5 0.0527(14) 0.0440(14) 0.0387(12) -0.0061(10) 0.0030(10) -0.0013(11)
C6 0.0460(13) 0.0313(11) 0.0507(14) -0.0022(10) 0.0140(10) 0.0043(10)
C8 0.0339(11) 0.0266(11) 0.0400(12) 0.0004(9) 0.0007(9) 0.0017(8)
C9 0.0381(12) 0.0317(11) 0.0437(12) 0.0026(9) 0.0014(10) -0.0005(9)
C11 0.0477(13) 0.0468(14) 0.0402(13) 0.0048(10) -0.0093(10) 0.0046(11)
C12 0.0732(19) 0.0646(19) 0.0697(19) 0.0288(15) -0.0108(15) -0.0091(15)
C18 0.0344(11) 0.0328(11) 0.0309(10) 0.0051(8) 0.0015(8) -0.0002(9)
C19 0.0403(13) 0.0358(12) 0.0332(11) 0.0035(9) 0.0049(9) 0.0028(10)
C21 0.0637(16) 0.0366(13) 0.0522(14) -0.0092(11) 0.0169(12) 0.0030(11)
C22 0.0608(16) 0.0470(15) 0.0626(17) 0.0034(12) 0.0116(13) 0.0119(12)
C23 0.0507(14) 0.0355(12) 0.0416(12) 0.0010(10) 0.0028(10) 0.0019(10)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.221(3) . . yes
O9 C9 1.195(3) . . yes
O10 C9 1.316(3) . . yes
O10 C11 1.466(3) . . yes
O18 C18 1.214(3) . . yes
O19 C19 1.197(3) . . yes
O20 C19 1.320(3) . . yes
O20 C21 1.468(3) . . yes
N7 C1 1.431(3) . . yes
N7 C8 1.335(3) . . yes
N17 C3 1.433(3) . . yes
N17 C18 1.335(3) . . yes
N7 H7 0.8600 . . no
N17 H17 0.8600 . . no
C1 C2 1.402(3) . . no
C1 C6 1.388(3) . . no
C2 C23 1.502(3) . . no
C2 C3 1.403(3) . . no
C3 C4 1.383(3) . . no
C4 C5 1.377(3) . . no
C5 C6 1.382(3) . . no
C8 C9 1.535(3) . . no
C11 C12 1.476(4) . . no
C18 C19 1.543(3) . . no
C21 C22 1.484(3) . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C11 H11A 0.9700 . . no
C11 H11B 0.9700 . . no
C12 H12A 0.9600 . . no
C12 H12B 0.9600 . . no
C12 H12C 0.9600 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11 115.45(18) . . . yes
C19 O20 C21 117.29(18) . . . yes
C1 N7 C8 124.87(18) . . . yes
C3 N17 C18 123.98(17) . . . yes
C1 N7 H7 118.00 . . . no
C8 N7 H7 118.00 . . . no
C18 N17 H17 118.00 . . . no
C3 N17 H17 118.00 . . . no
N7 C1 C6 117.62(19) . . . yes
C2 C1 C6 121.9(2) . . . no
N7 C1 C2 120.4(2) . . . yes
C1 C2 C3 116.1(2) . . . no
C1 C2 C23 122.1(2) . . . no
C3 C2 C23 121.84(19) . . . no
N17 C3 C2 120.0(2) . . . yes
C2 C3 C4 122.1(2) . . . no
N17 C3 C4 117.9(2) . . . yes
C3 C4 C5 120.4(2) . . . no
C4 C5 C6 119.4(2) . . . no
C1 C6 C5 120.1(2) . . . no
N7 C8 C9 112.1(2) . . . yes
O8 C8 N7 125.7(2) . . . yes
O8 C8 C9 122.2(2) . . . yes
O9 C9 C8 122.4(2) . . . yes
O10 C9 C8 111.9(2) . . . yes
O9 C9 O10 125.7(2) . . . yes
O10 C11 C12 108.9(2) . . . yes
O18 C18 N17 125.6(2) . . . yes
O18 C18 C19 122.35(19) . . . yes
N17 C18 C19 112.0(2) . . . yes
O19 C19 C18 122.3(2) . . . yes
O20 C19 C18 111.2(2) . . . yes
O19 C19 O20 126.5(2) . . . yes
O20 C21 C22 111.21(19) . . . yes
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
O10 C11 H11A 110.00 . . . no
O10 C11 H11B 110.00 . . . no
C12 C11 H11A 110.00 . . . no
C12 C11 H11B 110.00 . . . no
H11A C11 H11B 108.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
C11 C12 H12C 109.00 . . . no
H12A C12 H12B 109.00 . . . no
H12A C12 H12C 110.00 . . . no
H12B C12 H12C 109.00 . . . no
O20 C21 H21A 109.00 . . . no
O20 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 109.00 . . . no
H22A C22 H22B 109.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no
C2 C23 H23A 109.00 . . . no
C2 C23 H23B 109.00 . . . no
C2 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 110.00 . . . no

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
C11 O10 C9 C8 178.47(17) . . . . no
C9 O10 C11 C12 -169.4(2) . . . . no
C11 O10 C9 O9 -1.4(3) . . . . no
C21 O20 C19 O19 0.7(4) . . . . no
C21 O20 C19 C18 -177.78(17) . . . . no
C19 O20 C21 C22 -90.2(2) . . . . no
C8 N7 C1 C2 64.4(3) . . . . no
C8 N7 C1 C6 -117.0(2) . . . . no
C1 N7 C8 C9 -178.75(19) . . . . no
C1 N7 C8 O8 -0.2(4) . . . . no
C3 N17 C18 C19 -179.40(19) . . . . no
C18 N17 C3 C4 -113.7(2) . . . . no
C3 N17 C18 O18 -0.8(3) . . . . no
C18 N17 C3 C2 67.4(3) . . . . no
C2 C1 C6 C5 0.4(3) . . . . no
N7 C1 C6 C5 -178.2(2) . . . . no
C6 C1 C2 C23 -179.7(2) . . . . no
N7 C1 C2 C3 178.19(16) . . . . no
C6 C1 C2 C3 -0.4(3) . . . . no
N7 C1 C2 C23 -1.1(3) . . . . no
C1 C2 C3 N17 179.16(16) . . . . no
C23 C2 C3 C4 179.5(2) . . . . no
C23 C2 C3 N17 -1.6(3) . . . . no
C1 C2 C3 C4 0.3(3) . . . . no
C2 C3 C4 C5 -0.2(3) . . . . no
N17 C3 C4 C5 -179.1(2) . . . . no
C3 C4 C5 C6 0.1(4) . . . . no
C4 C5 C6 C1 -0.3(4) . . . . no
N7 C8 C9 O10 -169.14(18) . . . . no
N7 C8 C9 O9 10.7(3) . . . . no
O8 C8 C9 O9 -167.9(2) . . . . no
O8 C8 C9 O10 12.3(3) . . . . no
O18 C18 C19 O19 -177.3(2) . . . . no
O18 C18 C19 O20 1.3(3) . . . . no
N17 C18 C19 O19 1.5(3) . . . . no
N17 C18 C19 O20 179.97(18) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 O10 2.693(2) . . no
O8 C2 3.223(3) . . no
O8 C23 3.115(3) . . no
O8 N17 2.995(2) . 3_656 no
O9 C21 3.371(3) . 2_746 no
O9 C4 3.406(3) . 3_756 no
O9 N7 2.695(3) . . no
O10 O8 2.693(2) . . no
O18 C23 3.156(3) . . no
O18 O20 2.677(2) . . no
O18 C2 3.230(3) . . no
O18 N7 3.074(2) . 3_756 no
O19 C22 3.360(3) . . no
O19 N17 2.693(2) . . no
O20 O18 2.677(2) . . no
O8 H23B 2.5800 . . no
O8 H17 2.3200 . 3_656 no
O8 H22A 2.7700 . 2_646 no
O8 H5 2.8100 . 1_556 no
O8 H4 2.9000 . 3_656 no
O9 H21A 2.7100 . 2_746 no
O9 H11B 2.5200 . . no
O9 H11A 2.7600 . . no
O9 H7 2.3100 . . no
O10 H12A 2.8000 . 4_544 no
O18 H23A 2.4400 . . no
O18 H11A 2.5900 . 3_757 no
O18 H7 2.3900 . 3_756 no
O19 H21B 2.4200 . . no
O19 H12B 2.6600 . 2_656 no
O19 H17 2.3100 . . no
O20 H11B 2.6500 . 2_756 no
N7 O9 2.695(3) . . no
N7 O18 3.074(2) . 3_756 no
N17 O19 2.693(2) . . no
N17 O8 2.995(2) . 3_656 no
N7 H23B 2.4600 . . no
N17 H23A 2.8700 . . no
N17 H23C 2.8500 . . no
C2 O8 3.223(3) . . no
C2 O18 3.230(3) . . no
C4 O9 3.406(3) . 3_756 no
C8 C23 3.176(3) . . no
C9 C12 3.524(4) . 4_544 no
C12 C9 3.524(4) . 4_545 no
C18 C23 3.187(3) . . no
C19 C22 3.495(3) . 4_555 no
C19 C21 3.516(3) . 4_554 no
C21 C19 3.516(3) . 4_555 no
C21 O9 3.371(3) . 2_756 no
C22 O19 3.360(3) . . no
C22 C19 3.495(3) . 4_554 no
C23 O18 3.156(3) . . no
C23 C8 3.176(3) . . no
C23 O8 3.115(3) . . no
C23 C18 3.187(3) . . no
C1 H17 2.9100 . 3_656 no
C2 H7 3.0900 . 3_756 no
C3 H7 2.8700 . 3_756 no
C4 H23C 2.9100 . 3_656 no
C8 H17 3.0600 . 3_656 no
C8 H23B 2.4900 . . no
C9 H12A 2.8300 . 4_544 no
C11 H12A 2.9600 . 4_544 no
C11 H22C 3.0900 . 2_746 no
C18 H21A 2.8700 . 4_554 no
C18 H23A 2.7300 . . no
C19 H22B 2.9800 . . no
C19 H21A 2.8800 . 4_554 no
C19 H22B 2.9400 . 4_555 no
H4 O8 2.9000 . 3_656 no
H5 O8 2.8100 . 1_554 no
H5 H22A 2.5900 . 2_645 no
H6 H12C 2.5700 . 1_554 no
H7 O9 2.3100 . . no
H7 O18 2.3900 . 3_756 no
H7 C2 3.0900 . 3_756 no
H7 C3 2.8700 . 3_756 no
H11A O9 2.7600 . . no
H11A O18 2.5900 . 3_757 no
H11A H23A 2.5000 . 3_757 no
H11B O9 2.5200 . . no
H11B O20 2.6500 . 2_746 no
H11B H12A 2.3900 . 4_544 no
H12A O10 2.8000 . 4_545 no
H12A C9 2.8300 . 4_545 no
H12A C11 2.9600 . 4_545 no
H12A H11B 2.3900 . 4_545 no
H12B O19 2.6600 . 2_646 no
H12C H6 2.5700 . 1_556 no
H12C H22B 2.5900 . 2_646 no
H17 O19 2.3100 . . no
H17 O8 2.3200 . 3_656 no
H17 C1 2.9100 . 3_656 no
H17 C8 3.0600 . 3_656 no
H21A O9 2.7100 . 2_756 no
H21A C18 2.8700 . 4_555 no
H21A C19 2.8800 . 4_555 no
H21B O19 2.4200 . . no
H22A O8 2.7700 . 2_656 no
H22A H5 2.5900 . 2_655 no
H22B C19 2.9800 . . no
H22B H12C 2.5900 . 2_656 no
H22B C19 2.9400 . 4_554 no
H22C C11 3.0900 . 2_756 no
H23A O18 2.4400 . . no
H23A N17 2.8700 . . no
H23A C18 2.7300 . . no
H23A H11A 2.5000 . 3_757 no
H23B O8 2.5800 . . no
H23B N7 2.4600 . . no
H23B C8 2.4900 . . no
H23C N17 2.8500 . . no
H23C C4 2.9100 . 3_656 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.3100 2.695(3) 107.00 . yes
N7 H7 O18 0.8600 2.3900 3.074(2) 137.00 3_756 yes
N17 H17 O19 0.8600 2.3100 2.693(2) 107.00 . yes
N17 H17 O8 0.8600 2.3200 2.995(2) 136.00 3_656 yes
C11 H11A O18 0.9700 2.5900 3.433(3) 145.00 3_757 yes
C23 H23A O18 0.9600 2.4400 3.156(3) 131.00 . yes
C23 H23B O8 0.9600 2.5800 3.115(3) 115.00 . yes
C23 H23B N7 0.9600 2.4600 2.924(3) 110.00 . yes

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.041

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;

data_srl30
_database_code_depnum_ccdc_archive 'CCDC 801211'
#TrackingRef 'compuesto3.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Diethyl N,N'-[1,3-(2,4,6-trimethyl)phenylene]dioxamalate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H22 N2 O6'
_chemical_formula_sum            'C17 H22 N2 O6'
_chemical_formula_weight         350.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.0352(7)
_cell_length_b                   16.0173(14)
_cell_length_c                   14.3980(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.681(2)
_cell_angle_gamma                90
_cell_volume                     1807.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker APEXII area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            10973
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_sigmaI/netI    0.1386
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3184
_reflns_number_gt                1323
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 2008) and WINGX-2003 (Farrugia, 1999)'

_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^)+(0.0043P)^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     SHELXL
_refine_ls_extinction_coef       0.236(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3184
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani 0.4936(3) 0.05857(15) -0.14020(17) 1.000 0.0687(11) . .
O9 O Uani 0.4433(3) 0.26135(18) -0.2272(2) 1.000 0.0920(14) . .
O10 O Uani 0.3076(3) 0.14524(16) -0.2837(2) 1.000 0.0890(12) . .
O18 O Uani 0.8369(3) 0.18701(15) 0.31136(17) 1.000 0.0699(11) . .
O19 O Uani 0.5626(4) 0.03203(18) 0.35778(19) 1.000 0.0903(12) . .
O20 O Uani 0.7004(3) 0.13302(16) 0.4509(2) 1.000 0.0753(12) . .
N7 N Uani 0.6736(3) 0.16890(16) -0.1011(2) 1.000 0.0517(11) . .
N17 N Uani 0.7448(3) 0.07098(16) 0.2246(2) 1.000 0.0523(11) . .
C1 C Uani 0.7789(4) 0.1355(2) -0.0174(3) 1.000 0.0458(14) . .
C2 C Uani 0.7099(4) 0.11832(19) 0.0611(3) 1.000 0.0454(14) . .
C3 C Uani 0.8177(4) 0.09003(19) 0.1451(3) 1.000 0.0450(14) . .
C4 C Uani 0.9922(5) 0.0804(2) 0.1523(3) 1.000 0.0560(16) . .
C5 C Uani 1.0548(4) 0.0974(2) 0.0720(3) 1.000 0.0599(16) . .
C6 C Uani 0.9531(5) 0.1249(2) -0.0132(3) 1.000 0.0542(16) . .
C8 C Uani 0.5349(4) 0.1300(3) -0.1518(3) 1.000 0.0516(17) . .
C9 C Uani 0.4247(5) 0.1868(3) -0.2264(3) 1.000 0.0574(17) . .
C11 C Uani 0.1876(6) 0.1933(3) -0.3571(4) 1.000 0.124(3) . .
C12 C Uani 0.1282(6) 0.1374(4) -0.4391(3) 1.000 0.143(3) . .
C18 C Uani 0.7591(5) 0.1214(3) 0.2994(3) 1.000 0.0520(17) . .
C19 C Uani 0.6608(5) 0.0889(3) 0.3712(3) 1.000 0.0588(17) . .
C21 C Uani 0.6190(7) 0.1066(3) 0.5271(4) 1.000 0.121(3) . .
C22 C Uani 0.6944(6) 0.1468(3) 0.6146(3) 1.000 0.112(3) . .
C23 C Uani 0.5219(4) 0.13139(19) 0.0578(3) 1.000 0.0569(14) . .
C24 C Uani 1.0311(4) 0.1416(2) -0.0985(3) 1.000 0.0722(19) . .
C25 C Uani 1.1110(4) 0.0531(2) 0.2437(3) 1.000 0.0799(17) . .
H5 H Uiso 1.17071 0.09001 0.07529 1.000 0.0720 . .
H7 H Uiso 0.69993 0.21684 -0.12064 1.000 0.0621 . .
H11A H Uiso 0.09158 0.21241 -0.33208 1.000 0.1493 . .
H11B H Uiso 0.24445 0.24162 -0.37639 1.000 0.1493 . .
H12A H Uiso 0.07063 0.09030 -0.41944 1.000 0.2132 . .
H12B H Uiso 0.22433 0.11844 -0.46284 1.000 0.2132 . .
H12C H Uiso 0.05110 0.16718 -0.48837 1.000 0.2132 . .
H17 H Uiso 0.68936 0.02499 0.22404 1.000 0.0624 . .
H21A H Uiso 0.49838 0.11990 0.50996 1.000 0.1447 . .
H21B H Uiso 0.63015 0.04655 0.53512 1.000 0.1447 . .
H22A H Uiso 0.81331 0.13275 0.63229 1.000 0.1672 . .
H22B H Uiso 0.63845 0.12850 0.66349 1.000 0.1672 . .
H22C H Uiso 0.68214 0.20616 0.60699 1.000 0.1672 . .
H23A H Uiso 0.48069 0.17774 0.01697 1.000 0.0850 . .
H23B H Uiso 0.50631 0.14276 0.12083 1.000 0.0850 . .
H23C H Uiso 0.45973 0.08196 0.03366 1.000 0.0850 . .
H24A H Uiso 0.96159 0.11642 -0.15424 1.000 0.1077 . .
H24B H Uiso 1.14380 0.11822 -0.08710 1.000 0.1077 . .
H24C H Uiso 1.03731 0.20075 -0.10814 1.000 0.1077 . .
H25A H Uiso 1.05838 0.00911 0.27233 1.000 0.1200 . .
H25B H Uiso 1.13411 0.09958 0.28670 1.000 0.1200 . .
H25C H Uiso 1.21584 0.03328 0.23012 1.000 0.1200 . .

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
O8 0.083(2) 0.0478(16) 0.068(2) 0.0046(14) 0.0008(14) -0.0177(15)
O9 0.093(2) 0.067(2) 0.102(3) 0.0202(18) -0.0092(17) -0.0024(17)
O10 0.081(2) 0.080(2) 0.087(2) 0.0120(17) -0.0227(17) -0.0123(17)
O18 0.088(2) 0.0534(17) 0.072(2) -0.0120(15) 0.0255(15) -0.0210(15)
O19 0.113(2) 0.089(2) 0.075(2) -0.0143(18) 0.0341(18) -0.0419(19)
O20 0.089(2) 0.081(2) 0.059(2) -0.0097(17) 0.0230(16) -0.0145(16)
N7 0.0516(19) 0.0440(18) 0.057(2) 0.0103(16) 0.0068(16) -0.0045(15)
N17 0.062(2) 0.0448(19) 0.049(2) 0.0013(17) 0.0097(16) -0.0130(15)
C1 0.045(2) 0.040(2) 0.050(3) -0.0007(19) 0.005(2) -0.0030(18)
C2 0.045(2) 0.040(2) 0.050(3) -0.0057(19) 0.008(2) -0.0044(18)
C3 0.047(2) 0.043(2) 0.045(3) -0.0038(18) 0.010(2) -0.0062(18)
C4 0.047(3) 0.050(2) 0.067(3) 0.008(2) 0.004(2) -0.0002(19)
C5 0.041(2) 0.067(3) 0.071(3) 0.008(2) 0.011(2) 0.0032(19)
C6 0.057(3) 0.049(2) 0.059(3) 0.000(2) 0.018(2) 0.001(2)
C8 0.054(3) 0.058(3) 0.043(3) -0.002(2) 0.0108(19) -0.004(2)
C9 0.055(3) 0.055(3) 0.061(3) 0.006(2) 0.010(2) 0.000(2)
C11 0.093(4) 0.109(4) 0.136(5) 0.039(4) -0.051(4) -0.006(3)
C12 0.084(4) 0.244(7) 0.084(4) 0.021(4) -0.015(3) 0.007(4)
C18 0.059(3) 0.051(3) 0.045(3) 0.001(2) 0.009(2) -0.001(2)
C19 0.065(3) 0.058(3) 0.050(3) -0.004(2) 0.005(2) -0.004(2)
C21 0.136(5) 0.170(5) 0.072(4) -0.037(4) 0.058(3) -0.058(4)
C22 0.140(4) 0.137(5) 0.068(4) 0.011(3) 0.045(3) 0.026(4)
C23 0.053(2) 0.062(2) 0.055(3) 0.003(2) 0.0106(18) 0.004(2)
C24 0.065(3) 0.079(3) 0.080(4) 0.004(2) 0.032(2) 0.005(2)
C25 0.064(3) 0.093(3) 0.072(3) 0.015(3) -0.008(2) 0.008(2)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.213(5) . . yes
O9 C9 1.204(6) . . yes
O10 C9 1.292(5) . . yes
O10 C11 1.481(6) . . yes
O18 C18 1.216(5) . . yes
O19 C19 1.193(5) . . yes
O20 C19 1.326(5) . . yes
O20 C21 1.458(6) . . yes
N7 C1 1.417(5) . . yes
N7 C8 1.344(5) . . yes
N17 C3 1.429(5) . . yes
N17 C18 1.331(5) . . yes
N7 H7 0.8600 . . no
N17 H17 0.8600 . . no
C1 C6 1.398(5) . . no
C1 C2 1.391(6) . . no
C2 C3 1.399(6) . . no
C2 C23 1.515(5) . . no
C3 C4 1.392(5) . . no
C4 C5 1.385(6) . . no
C4 C25 1.511(6) . . no
C5 C6 1.388(6) . . no
C6 C24 1.520(6) . . no
C8 C9 1.532(6) . . no
C11 C12 1.475(7) . . no
C18 C19 1.524(6) . . no
C21 C22 1.426(7) . . no
C5 H5 0.9300 . . no
C11 H11A 0.9700 . . no
C11 H11B 0.9700 . . no
C12 H12A 0.9600 . . no
C12 H12B 0.9600 . . no
C12 H12C 0.9600 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9600 . . no
C22 H22B 0.9600 . . no
C22 H22C 0.9600 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no
C24 H24A 0.9600 . . no
C24 H24B 0.9600 . . no
C24 H24C 0.9600 . . no
C25 H25A 0.9600 . . no
C25 H25B 0.9600 . . no
C25 H25C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11 117.2(3) . . . yes
C19 O20 C21 115.8(3) . . . yes
C1 N7 C8 123.8(3) . . . yes
C3 N17 C18 122.8(3) . . . yes
C8 N7 H7 118.00 . . . no
C1 N7 H7 118.00 . . . no
C18 N17 H17 119.00 . . . no
C3 N17 H17 119.00 . . . no
C2 C1 C6 121.0(4) . . . no
N7 C1 C6 119.2(3) . . . yes
N7 C1 C2 119.7(3) . . . yes
C1 C2 C23 121.3(3) . . . no
C3 C2 C23 119.7(3) . . . no
C1 C2 C3 119.0(3) . . . no
N17 C3 C2 118.5(3) . . . yes
N17 C3 C4 120.0(3) . . . yes
C2 C3 C4 121.5(4) . . . no
C3 C4 C5 117.4(4) . . . no
C3 C4 C25 122.0(4) . . . no
C5 C4 C25 120.5(3) . . . no
C4 C5 C6 123.3(3) . . . no
C1 C6 C5 117.8(4) . . . no
C1 C6 C24 122.0(4) . . . no
C5 C6 C24 120.2(3) . . . no
N7 C8 C9 112.8(4) . . . yes
O8 C8 N7 125.6(4) . . . yes
O8 C8 C9 121.5(3) . . . yes
O9 C9 C8 122.8(4) . . . yes
O10 C9 C8 111.7(4) . . . yes
O9 C9 O10 125.4(4) . . . yes
O10 C11 C12 107.5(4) . . . yes
O18 C18 N17 126.1(4) . . . yes
O18 C18 C19 121.8(4) . . . yes
N17 C18 C19 112.1(4) . . . yes
O19 C19 C18 125.0(4) . . . yes
O20 C19 C18 110.1(4) . . . yes
O19 C19 O20 124.9(4) . . . yes
O20 C21 C22 111.1(4) . . . yes
C4 C5 H5 118.00 . . . no
C6 C5 H5 118.00 . . . no
O10 C11 H11A 110.00 . . . no
O10 C11 H11B 110.00 . . . no
C12 C11 H11A 110.00 . . . no
C12 C11 H11B 110.00 . . . no
H11A C11 H11B 109.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
C11 C12 H12C 109.00 . . . no
H12A C12 H12B 110.00 . . . no
H12A C12 H12C 110.00 . . . no
H12B C12 H12C 109.00 . . . no
O20 C21 H21A 109.00 . . . no
O20 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
C21 C22 H22A 109.00 . . . no
C21 C22 H22B 109.00 . . . no
C21 C22 H22C 109.00 . . . no
H22A C22 H22B 109.00 . . . no
H22A C22 H22C 109.00 . . . no
H22B C22 H22C 109.00 . . . no
C2 C23 H23A 109.00 . . . no
C2 C23 H23B 109.00 . . . no
C2 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 110.00 . . . no
H23B C23 H23C 109.00 . . . no
C6 C24 H24A 110.00 . . . no
C6 C24 H24B 110.00 . . . no
C6 C24 H24C 110.00 . . . no
H24A C24 H24B 109.00 . . . no
H24A C24 H24C 109.00 . . . no
H24B C24 H24C 109.00 . . . no
C4 C25 H25A 109.00 . . . no
C4 C25 H25B 109.00 . . . no
C4 C25 H25C 109.00 . . . no
H25A C25 H25B 109.00 . . . no
H25A C25 H25C 109.00 . . . no
H25B C25 H25C 109.00 . . . no

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
C11 O10 C9 C8 177.7(3) . . . . no
C9 O10 C11 C12 152.0(4) . . . . no
C11 O10 C9 O9 0.7(6) . . . . no
C19 O20 C21 C22 168.6(4) . . . . no
C21 O20 C19 C18 -178.1(4) . . . . no
C21 O20 C19 O19 1.9(6) . . . . no
C1 N7 C8 C9 168.3(3) . . . . no
C1 N7 C8 O8 -9.5(6) . . . . no
C8 N7 C1 C6 123.4(4) . . . . no
C8 N7 C1 C2 -60.4(5) . . . . no
C3 N17 C18 C19 176.5(3) . . . . no
C18 N17 C3 C4 76.5(4) . . . . no
C3 N17 C18 O18 -2.1(6) . . . . no
C18 N17 C3 C2 -103.5(4) . . . . no
C6 C1 C2 C23 178.7(3) . . . . no
N7 C1 C6 C5 175.7(3) . . . . no
C2 C1 C6 C24 178.8(3) . . . . no
C6 C1 C2 C3 0.0(5) . . . . no
N7 C1 C2 C23 2.5(5) . . . . no
C2 C1 C6 C5 -0.5(5) . . . . no
N7 C1 C6 C24 -5.0(5) . . . . no
N7 C1 C2 C3 -176.2(3) . . . . no
C23 C2 C3 C4 -177.4(3) . . . . no
C23 C2 C3 N17 2.5(4) . . . . no
C1 C2 C3 N17 -178.8(3) . . . . no
C1 C2 C3 C4 1.3(5) . . . . no
N17 C3 C4 C5 178.1(3) . . . . no
N17 C3 C4 C25 -2.3(5) . . . . no
C2 C3 C4 C5 -2.0(5) . . . . no
C2 C3 C4 C25 177.6(3) . . . . no
C25 C4 C5 C6 -178.2(3) . . . . no
C3 C4 C5 C6 1.4(5) . . . . no
C4 C5 C6 C1 -0.2(5) . . . . no
C4 C5 C6 C24 -179.5(3) . . . . no
N7 C8 C9 O10 170.0(3) . . . . no
N7 C8 C9 O9 -12.9(6) . . . . no
O8 C8 C9 O9 165.0(4) . . . . no
O8 C8 C9 O10 -12.1(5) . . . . no
O18 C18 C19 O19 168.6(4) . . . . no
O18 C18 C19 O20 -11.5(6) . . . . no
N17 C18 C19 O19 -10.1(6) . . . . no
N17 C18 C19 O20 169.9(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 O10 2.660(4) . . no
O8 C2 3.182(5) . . no
O8 C23 3.042(5) . . no
O8 N17 2.903(4) . 3_655 no
O8 C23 3.278(4) . 3_655 no
O9 C19 3.119(5) . 4_554 no
O9 C18 3.112(5) . 4_554 no
O9 N7 2.727(4) . . no
O9 O18 3.198(4) . 4_554 no
O10 O8 2.660(4) . . no
O18 N7 3.060(4) . 4_555 no
O18 O20 2.637(4) . . no
O18 C4 3.313(5) . . no
O18 O9 3.198(4) . 4_555 no
O18 C24 3.281(4) . 4_555 no
O18 C25 3.368(4) . . no
O19 N17 2.728(4) . . no
O19 C21 3.297(6) . 3_656 no
O20 N7 3.256(4) . 4_555 no
O20 O18 2.637(4) . . no
O8 H17 2.1500 . 3_655 no
O8 H23C 2.6000 . . no
O8 H23C 2.7000 . 3_655 no
O9 H23B 2.8100 . 4_554 no
O9 H11B 2.4000 . . no
O9 H7 2.3900 . . no
O10 H17 2.8600 . 3_655 no
O18 H7 2.2400 . 4_555 no
O18 H24C 2.5200 . 4_555 no
O18 H25B 2.8600 . . no
O19 H21A 2.7500 . . no
O19 H21B 2.7200 . 3_656 no
O19 H21B 2.5000 . . no
O19 H17 2.3700 . . no
O20 H12C 2.8100 . 1_656 no
O20 H7 2.6200 . 4_555 no
N7 O9 2.727(4) . . no
N7 O20 3.256(4) . 4_554 no
N7 O18 3.060(4) . 4_554 no
N17 O19 2.728(4) . . no
N17 O8 2.903(4) . 3_655 no
N7 H24A 2.7200 . . no
N7 H23A 2.5400 . . no
N17 H23B 2.4400 . . no
N17 H25A 2.6500 . . no
C2 O8 3.182(5) . . no
C4 O18 3.313(5) . . no
C5 C11 3.597(6) . 4_655 no
C8 C23 3.043(6) . . no
C9 C22 3.539(6) . 1_554 no
C11 C5 3.597(6) . 4_454 no
C18 C25 3.291(5) . . no
C18 O9 3.112(5) . 4_555 no
C18 C23 3.584(6) . . no
C19 O9 3.119(5) . 4_555 no
C21 O19 3.297(6) . 3_656 no
C22 C9 3.539(6) . 1_556 no
C23 O8 3.042(5) . . no
C23 O8 3.278(4) . 3_655 no
C23 C18 3.584(6) . . no
C23 C8 3.043(6) . . no
C24 O18 3.281(4) . 4_554 no
C25 C18 3.291(5) . . no
C25 O18 3.368(4) . . no
C2 H22C 2.9100 . 4_554 no
C5 H11B 3.0000 . 4_655 no
C8 H22B 2.9600 . 1_554 no
C8 H23C 2.9700 . . no
C8 H23A 2.6700 . . no
C9 H22B 2.7400 . 1_554 no
C12 H22A 2.9300 . 1_454 no
C18 H7 2.9200 . 4_555 no
C18 H23B 2.9300 . . no
C18 H25B 3.0800 . . no
C18 H25A 3.1000 . . no
C23 H17 3.0000 . . no
C23 H5 2.9600 . 1_455 no
C23 H22C 2.9200 . 4_554 no
C24 H7 2.8700 . . no
C25 H24A 3.0100 . 3_755 no
H5 C23 2.9600 . 1_655 no
H5 H23C 2.5300 . 1_655 no
H5 H24B 2.3400 . . no
H5 H25C 2.3600 . . no
H7 O9 2.3900 . . no
H7 C24 2.8700 . . no
H7 O18 2.2400 . 4_554 no
H7 O20 2.6200 . 4_554 no
H7 C18 2.9200 . 4_554 no
H11A H22A 2.5300 . 1_454 no
H11B O9 2.4000 . . no
H11B C5 3.0000 . 4_454 no
H12A H22A 2.4400 . 1_454 no
H12B H21A 2.3200 . 1_554 no
H12C O20 2.8100 . 1_454 no
H17 O19 2.3700 . . no
H17 C23 3.0000 . . no
H17 O8 2.1500 . 3_655 no
H17 O10 2.8600 . 3_655 no
H21A O19 2.7500 . . no
H21A H12B 2.3200 . 1_556 no
H21B O19 2.5000 . . no
H21B O19 2.7200 . 3_656 no
H21B H21B 2.5900 . 3_656 no
H22A C12 2.9300 . 1_656 no
H22A H11A 2.5300 . 1_656 no
H22A H12A 2.4400 . 1_656 no
H22B C8 2.9600 . 1_556 no
H22B C9 2.7400 . 1_556 no
H22C C2 2.9100 . 4_555 no
H22C C23 2.9200 . 4_555 no
H23A N7 2.5400 . . no
H23A C8 2.6700 . . no
H23B N17 2.4400 . . no
H23B C18 2.9300 . . no
H23B O9 2.8100 . 4_555 no
H23C O8 2.6000 . . no
H23C C8 2.9700 . . no
H23C H5 2.5300 . 1_455 no
H23C O8 2.7000 . 3_655 no
H24A N7 2.7200 . . no
H24A C25 3.0100 . 3_755 no
H24B H5 2.3400 . . no
H24C O18 2.5200 . 4_554 no
H25A N17 2.6500 . . no
H25A C18 3.1000 . . no
H25B O18 2.8600 . . no
H25B C18 3.0800 . . no
H25C H5 2.3600 . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.3900 2.727(4) 104.00 . yes
N7 H7 O18 0.8600 2.2400 3.060(4) 160.00 4_554 yes
N17 H17 O19 0.8600 2.3700 2.728(4) 105.00 . yes
N17 H17 O8 0.8600 2.1500 2.903(4) 146.00 3_655 yes
C23 H23A N7 0.9600 2.5400 2.882(5) 101.00 . yes
C23 H23B N17 0.9600 2.4400 2.833(5) 104.00 . yes
C24 H24C O18 0.9600 2.5200 3.281(4) 136.00 4_554 yes

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.052

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;

data_Srl31
_database_code_depnum_ccdc_archive 'CCDC 801212'
#TrackingRef 'NEW-801212.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N,N'-Bis[2-(2-hydroxyethylamino)oxalyl]-1,3-(2-methyl)
phenylenediamine
;
_chemical_name_common            
;N,N'-Bis(2-(2-hydroxyethylamino)oxalyl)-1,3-(2-methyl)
phenylenediamine
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N4 O6'
_chemical_formula_sum            'C15 H20 N4 O6'
_chemical_formula_weight         352.35

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_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.0080(18)
_cell_length_b                   9.5510(19)
_cell_length_c                   10.5930(19)
_cell_angle_alpha                94.80(2)
_cell_angle_beta                 99.01(3)
_cell_angle_gamma                109.34(3)
_cell_volume                     840.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker APEXII area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            5214
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.1289
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2956
_reflns_number_gt                1440
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 2008) and WINGX-2003 (Farrugia, 1999)'

_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^)+(0.1267P)^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     SHELXL
_refine_ls_extinction_coef       0.76(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2956
_refine_ls_number_parameters     298
_refine_ls_number_restraints     170
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2432
_refine_ls_wR_factor_gt          0.2297
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani 1.0049(5) 0.3575(4) 0.0903(4) 1.000 0.1077(17) . .
O9 O Uani 1.3120(4) 0.5865(3) 0.3411(3) 1.000 0.0640(12) . .
O18 O Uani 0.6992(4) -0.3174(3) 0.4670(3) 1.000 0.0525(11) . .
O19 O Uani 0.4925(4) -0.1124(3) 0.6073(3) 1.000 0.0574(12) . .
O23A O Uani 0.3370(9) -0.4690(10) 0.9250(8) 0.504(8) 0.095(4) . .
N7 N Uani 1.0908(4) 0.3128(4) 0.2897(4) 1.000 0.0506(12) . .
N10 N Uani 1.1931(5) 0.6542(4) 0.1655(4) 1.000 0.0794(17) . .
N17 N Uani 0.6946(4) -0.0828(4) 0.4436(4) 1.000 0.0499(14) . .
N20 N Uani 0.4990(4) -0.3430(4) 0.6388(4) 1.000 0.0526(12) . .
C1 C Uani 0.9905(5) 0.1579(5) 0.2804(4) 1.000 0.0455(16) . .
C2 C Uani 0.8963(5) 0.1143(5) 0.3715(4) 1.000 0.0443(16) . .
C3 C Uani 0.8013(5) -0.0360(5) 0.3572(4) 1.000 0.0452(17) . .
C4 C Uani 0.8008(6) -0.1407(5) 0.2572(5) 1.000 0.0558(17) . .
C5 C Uani 0.8996(7) -0.0945(6) 0.1693(5) 1.000 0.0662(19) . .
C6 C Uani 0.9947(6) 0.0549(5) 0.1807(5) 1.000 0.0600(17) . .
C8 C Uani 1.0924(6) 0.3996(5) 0.1979(5) 1.000 0.0597(17) . .
C9 C Uani 1.2109(5) 0.5561(5) 0.2408(4) 1.000 0.0503(17) . .
C18 C Uani 0.6532(5) -0.2121(5) 0.4919(4) 1.000 0.0415(14) . .
C19 C Uani 0.5378(5) -0.2184(5) 0.5833(4) 1.000 0.0454(16) . .
C21 C Uani 0.3862(6) -0.3755(6) 0.7255(5) 1.000 0.0631(17) . .
C22 C Uani 0.4542(6) -0.4348(6) 0.8410(5) 1.000 0.080(3) . .
C24 C Uani 0.9016(5) 0.2276(5) 0.4824(4) 1.000 0.0540(17) . .
O13A O Uani 1.447(3) 1.0161(16) 0.125(2) 0.245(8) 0.120(5) . .
O13B O Uani 1.3191(19) 0.8929(18) -0.0150(14) 0.291(9) 0.104(4) . .
O13C O Uani 1.4384(15) 0.8277(14) 0.0399(13) 0.463(9) 0.118(4) . .
O23B O Uani 0.6062(9) -0.3298(9) 0.9163(7) 0.496(8) 0.110(4) . .
C11A C Uani 1.2582(5) 0.8172(4) 0.2000(4) 0.245(8) 0.086(3) . .
C11B C Uani 1.296(5) 0.8117(16) 0.185(3) 0.291(9) 0.086(3) . .
C11C C Uani 1.294(3) 0.8116(10) 0.2044(14) 0.463(9) 0.084(3) . .
C12A C Uani 1.379(3) 0.8526(16) 0.111(3) 0.245(8) 0.094(3) . .
C12B C Uani 1.420(3) 0.875(3) 0.100(2) 0.291(9) 0.095(3) . .
C12C C Uani 1.3297(17) 0.8936(14) 0.0885(13) 0.463(9) 0.084(3) . .
H22C H Uiso 0.46710 -0.52803 0.80746 1.000 0.0963 . .
H23A H Uiso 0.43674 -0.36686 0.97761 0.504(8) 0.1422 . .
H24A H Uiso 0.80618 0.19081 0.51743 1.000 0.0807 . .
H24B H Uiso 0.99396 0.24297 0.54841 1.000 0.0807 . .
H24C H Uiso 0.90815 0.32087 0.45187 1.000 0.0807 . .
H4 H Uiso 0.73486 -0.24055 0.24948 1.000 0.0670 . .
H5 H Uiso 0.90200 -0.16356 0.10300 1.000 0.0793 . .
H6 H Uiso 1.06130 0.08658 0.12213 1.000 0.0722 . .
H7 H Uiso 1.15605 0.35308 0.36195 1.000 0.0759 . .
H10 H Uiso 1.13782 0.61916 0.08866 1.000 0.1187 . .
H17 H Uiso 0.65128 -0.01993 0.46793 1.000 0.0747 . .
H20A H Uiso 0.54351 -0.40756 0.62208 1.000 0.0630 . .
H21A H Uiso 0.36711 -0.28498 0.75435 1.000 0.0759 . .
H21B H Uiso 0.28481 -0.44949 0.68054 1.000 0.0759 . .
H22B H Uiso 0.56394 -0.34818 0.88809 0.504(8) 0.1313 . .
H11A H Uiso 1.17690 0.86219 0.17992 0.245(8) 0.1034 . .
H11B H Uiso 1.30976 0.84775 0.29031 0.245(8) 0.1034 . .
H11C H Uiso 1.22558 0.86974 0.17925 0.291(9) 0.1034 . .
H11D H Uiso 1.35482 0.83444 0.27351 0.291(9) 0.1034 . .
H11E H Uiso 1.24123 0.86118 0.25604 0.463(9) 0.1007 . .
H11F H Uiso 1.39468 0.81762 0.25772 0.463(9) 0.1007 . .
H12A H Uiso 1.32655 0.81116 0.02176 0.245(8) 0.1128 . .
H12B H Uiso 1.46256 0.81135 0.13544 0.245(8) 0.1128 . .
H12C H Uiso 1.47352 0.80604 0.08011 0.291(9) 0.1143 . .
H12D H Uiso 1.49917 0.97084 0.14217 0.291(9) 0.1143 . .
H12E H Uiso 1.38115 1.00097 0.11486 0.463(9) 0.1001 . .
H12F H Uiso 1.23283 0.87392 0.02459 0.463(9) 0.1001 . .
H13A H Uiso 1.52480 1.04687 0.18487 0.245(8) 0.1793 . .
H13B H Uiso 1.37611 0.93541 -0.06357 0.291(9) 0.1556 . .
H13C H Uiso 1.41095 0.80482 -0.03880 0.463(9) 0.1761 . .
H22A H Uiso 0.37844 -0.43788 0.90359 0.496(8) 0.1313 . .
H23B H Uiso 0.64352 -0.37222 0.97441 0.496(8) 0.1642 . .

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
O8 0.130(3) 0.069(3) 0.072(3) 0.035(2) -0.042(3) -0.011(2)
O9 0.068(2) 0.054(2) 0.056(2) 0.0131(17) -0.0064(18) 0.0101(16)
O18 0.067(2) 0.0479(19) 0.053(2) 0.0163(16) 0.0156(16) 0.0297(16)
O19 0.066(2) 0.046(2) 0.068(2) 0.0154(17) 0.0231(17) 0.0235(17)
O23A 0.109(6) 0.094(6) 0.099(7) 0.033(5) 0.054(5) 0.038(5)
N7 0.052(2) 0.049(2) 0.045(2) 0.0142(19) 0.0042(17) 0.0109(18)
N10 0.093(3) 0.059(3) 0.062(3) 0.030(2) -0.011(2) 0.002(2)
N17 0.055(2) 0.041(2) 0.055(3) 0.0129(19) 0.0145(19) 0.0154(17)
N20 0.067(2) 0.039(2) 0.052(2) 0.0138(19) 0.018(2) 0.0141(19)
C1 0.049(2) 0.040(3) 0.044(3) 0.014(2) 0.003(2) 0.012(2)
C2 0.047(2) 0.041(3) 0.041(3) 0.009(2) 0.003(2) 0.012(2)
C3 0.053(3) 0.044(3) 0.044(3) 0.014(2) 0.014(2) 0.020(2)
C4 0.063(3) 0.044(3) 0.058(3) 0.007(2) 0.013(3) 0.015(2)
C5 0.098(4) 0.053(3) 0.050(3) 0.015(3) 0.021(3) 0.025(3)
C6 0.079(3) 0.054(3) 0.046(3) 0.013(3) 0.016(3) 0.019(3)
C8 0.067(3) 0.054(3) 0.047(3) 0.018(3) -0.006(3) 0.012(2)
C9 0.051(3) 0.052(3) 0.043(3) 0.015(2) 0.006(2) 0.011(2)
C18 0.048(2) 0.034(2) 0.041(3) 0.012(2) 0.004(2) 0.013(2)
C19 0.046(2) 0.040(3) 0.045(3) 0.009(2) 0.004(2) 0.010(2)
C21 0.080(3) 0.056(3) 0.058(3) 0.018(3) 0.024(3) 0.023(3)
C22 0.117(5) 0.074(4) 0.055(4) 0.026(3) 0.030(4) 0.031(4)
C24 0.053(3) 0.050(3) 0.055(3) 0.005(2) 0.012(2) 0.013(2)
O13A 0.154(11) 0.065(6) 0.092(10) 0.021(7) 0.012(8) -0.021(8)
O13B 0.127(9) 0.085(8) 0.060(6) 0.031(6) 0.009(6) -0.014(7)
O13C 0.152(7) 0.094(7) 0.090(7) 0.005(6) 0.037(6) 0.016(5)
O23B 0.147(8) 0.090(7) 0.051(5) 0.013(5) -0.012(5) 0.002(6)
C11A 0.119(7) 0.054(5) 0.059(6) 0.015(5) 0.006(5) -0.001(5)
C11B 0.120(6) 0.051(5) 0.058(5) 0.024(4) 0.003(5) -0.006(5)
C11C 0.116(6) 0.050(4) 0.060(5) 0.019(4) 0.007(4) -0.003(4)
C12A 0.123(6) 0.062(5) 0.064(5) 0.013(5) 0.009(5) -0.008(5)
C12B 0.128(6) 0.062(5) 0.063(5) 0.018(5) 0.008(5) -0.007(5)
C12C 0.118(6) 0.049(4) 0.060(5) 0.020(4) 0.004(5) 0.001(4)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.231(7) . . yes
O9 C9 1.230(5) . . yes
O13A C12A 1.46(2) . . yes
O13B C12B 1.46(3) . . yes
O13C C12C 1.46(2) . . yes
O18 C18 1.232(6) . . yes
O19 C19 1.233(6) . . yes
O23A C22 1.459(10) . . yes
O23B C22 1.460(10) . . yes
O13A H13A 0.8200 . . no
O13B H13B 0.8200 . . no
O13C H13C 0.8200 . . no
O23A H23A 1.1100 . . no
O23B H23B 0.8500 . . no
N7 C1 1.441(6) . . yes
N7 C8 1.328(6) . . yes
N10 C11B 1.46(2) . . yes
N10 C11A 1.461(5) . . yes
N10 C9 1.313(6) . . yes
N10 C11C 1.459(12) . . yes
N17 C18 1.337(6) . . yes
N17 C3 1.422(6) . . yes
N20 C19 1.338(6) . . yes
N20 C21 1.450(7) . . yes
N7 H7 0.8600 . . no
N10 H10 0.8600 . . no
N17 H17 0.8600 . . no
N20 H20A 0.8600 . . no
C1 C2 1.384(6) . . no
C1 C6 1.396(7) . . no
C2 C24 1.513(6) . . no
C2 C3 1.388(6) . . no
C3 C4 1.393(7) . . no
C4 C5 1.386(8) . . no
C5 C6 1.383(7) . . no
C8 C9 1.503(7) . . no
C11A C12A 1.52(3) . . no
C11B C12B 1.54(4) . . no
C11C C12C 1.530(19) . . no
C18 C19 1.518(6) . . no
C21 C22 1.518(8) . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C6 H6 0.9300 . . no
C11A H11B 0.9700 . . no
C11A H11A 0.9700 . . no
C11B H11D 0.9700 . . no
C11B H11C 0.9700 . . no
C11C H11E 0.9700 . . no
C11C H11F 0.9700 . . no
C12A H12A 0.9700 . . no
C12A H12B 0.9700 . . no
C12B H12C 0.9600 . . no
C12B H12D 0.9700 . . no
C12C H12E 0.9700 . . no
C12C H12F 0.9700 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22C 0.9800 . . no
C22 H22A 1.0200 . . no
C22 H22B 1.0700 . . no
C24 H24B 0.9600 . . no
C24 H24C 0.9600 . . no
C24 H24A 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A O13A H13A 109.00 . . . no
C12B O13B H13B 109.00 . . . no
C12C O13C H13C 109.00 . . . no
C22 O23A H23A 75.00 . . . no
C22 O23B H23B 110.00 . . . no
C1 N7 C8 126.5(4) . . . yes
C9 N10 C11B 124.8(14) . . . yes
C9 N10 C11C 118.8(8) . . . yes
C9 N10 C11A 126.2(4) . . . yes
C3 N17 C18 128.2(4) . . . yes
C19 N20 C21 123.8(4) . . . yes
C8 N7 H7 117.00 . . . no
C1 N7 H7 117.00 . . . no
C9 N10 H10 117.00 . . . no
C11C N10 H10 123.00 . . . no
C11A N10 H10 117.00 . . . no
C11B N10 H10 115.00 . . . no
C18 N17 H17 116.00 . . . no
C3 N17 H17 116.00 . . . no
C19 N20 H20A 118.00 . . . no
C21 N20 H20A 118.00 . . . no
N7 C1 C6 118.6(4) . . . yes
N7 C1 C2 119.7(4) . . . yes
C2 C1 C6 121.8(4) . . . no
C3 C2 C24 122.6(4) . . . no
C1 C2 C3 117.2(4) . . . no
C1 C2 C24 120.3(4) . . . no
N17 C3 C2 118.7(4) . . . yes
N17 C3 C4 119.0(4) . . . yes
C2 C3 C4 122.3(4) . . . no
C3 C4 C5 119.3(4) . . . no
C4 C5 C6 119.7(5) . . . no
C1 C6 C5 119.8(5) . . . no
O8 C8 C9 123.6(4) . . . yes
O8 C8 N7 123.9(4) . . . yes
N7 C8 C9 112.5(4) . . . yes
O9 C9 C8 120.9(4) . . . yes
N10 C9 C8 114.7(4) . . . yes
O9 C9 N10 124.4(4) . . . yes
N10 C11A C12A 98.5(7) . . . yes
N10 C11B C12B 123(2) . . . yes
N10 C11C C12C 112.4(10) . . . yes
O13A C12A C11A 105.9(19) . . . yes
O13B C12B C11B 102(2) . . . yes
O13C C12C C11C 101.6(13) . . . yes
O18 C18 C19 121.9(4) . . . yes
N17 C18 C19 112.2(4) . . . yes
O18 C18 N17 125.9(4) . . . yes
N20 C19 C18 114.3(4) . . . yes
O19 C19 C18 121.3(4) . . . yes
O19 C19 N20 124.3(4) . . . yes
N20 C21 C22 109.4(5) . . . yes
O23A C22 C21 108.1(5) . . . yes
O23B C22 C21 113.9(5) . . . yes
C5 C4 H4 120.00 . . . no
C3 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
C12A C11A H11A 112.00 . . . no
N10 C11A H11A 112.00 . . . no
N10 C11A H11B 112.00 . . . no
H11A C11A H11B 110.00 . . . no
C12A C11A H11B 112.00 . . . no
C12B C11B H11D 107.00 . . . no
C12B C11B H11C 107.00 . . . no
N10 C11B H11C 107.00 . . . no
H11C C11B H11D 107.00 . . . no
N10 C11B H11D 107.00 . . . no
N10 C11C H11E 109.00 . . . no
N10 C11C H11F 109.00 . . . no
H11E C11C H11F 108.00 . . . no
C12C C11C H11E 109.00 . . . no
C12C C11C H11F 109.00 . . . no
O13A C12A H12A 110.00 . . . no
O13A C12A H12B 110.00 . . . no
C11A C12A H12A 111.00 . . . no
C11A C12A H12B 111.00 . . . no
H12A C12A H12B 108.00 . . . no
C11B C12B H12D 111.00 . . . no
O13B C12B H12C 112.00 . . . no
O13B C12B H12D 111.00 . . . no
H12C C12B H12D 110.00 . . . no
C11B C12B H12C 111.00 . . . no
O13C C12C H12E 111.00 . . . no
O13C C12C H12F 111.00 . . . no
H12E C12C H12F 109.00 . . . no
C11C C12C H12E 111.00 . . . no
C11C C12C H12F 111.00 . . . no
N20 C21 H21B 110.00 . . . no
H21A C21 H21B 108.00 . . . no
C22 C21 H21A 110.00 . . . no
C22 C21 H21B 110.00 . . . no
N20 C21 H21A 110.00 . . . no
C21 C22 H22C 107.00 . . . no
C21 C22 H22A 105.00 . . . no
H22B C22 H22C 114.00 . . . no
O23B C22 H22C 110.00 . . . no
H22A C22 H22C 119.00 . . . no
O23B C22 H22A 102.00 . . . no
O23A C22 H22C 109.00 . . . no
C21 C22 H22B 107.00 . . . no
O23A C22 H22B 112.00 . . . no
C2 C24 H24C 110.00 . . . no
H24A C24 H24C 109.00 . . . no
H24B C24 H24C 109.00 . . . no
H24A C24 H24B 109.00 . . . no
C2 C24 H24A 109.00 . . . no
C2 C24 H24B 109.00 . . . no

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
C8 N7 C1 C2 -125.9(5) . . . . no
C8 N7 C1 C6 55.8(7) . . . . no
C1 N7 C8 O8 0.5(9) . . . . no
C1 N7 C8 C9 179.4(4) . . . . no
C3 N17 C18 O18 -1.7(8) . . . . no
C18 N17 C3 C2 -144.6(5) . . . . no
C18 N17 C3 C4 38.7(7) . . . . no
C3 N17 C18 C19 179.0(4) . . . . no
C21 N20 C19 O19 6.1(7) . . . . no
C19 N20 C21 C22 -135.7(5) . . . . no
C21 N20 C19 C18 -177.6(4) . . . . no
N7 C1 C2 C24 -1.6(7) . . . . no
C6 C1 C2 C24 176.7(4) . . . . no
C2 C1 C6 C5 1.8(8) . . . . no
N7 C1 C2 C3 179.6(4) . . . . no
N7 C1 C6 C5 -179.9(5) . . . . no
C6 C1 C2 C3 -2.2(7) . . . . no
C1 C2 C3 N17 -175.6(4) . . . . no
C24 C2 C3 C4 -177.9(5) . . . . no
C1 C2 C3 C4 0.9(7) . . . . no
C24 C2 C3 N17 5.6(7) . . . . no
N17 C3 C4 C5 177.3(5) . . . . no
C2 C3 C4 C5 0.8(8) . . . . no
C3 C4 C5 C6 -1.2(8) . . . . no
C4 C5 C6 C1 0.0(8) . . . . no
O8 C8 C9 N10 13.1(8) . . . . no
O8 C8 C9 O9 -168.9(5) . . . . no
N7 C8 C9 N10 -165.9(4) . . . . no
N7 C8 C9 O9 12.2(7) . . . . no
O18 C18 C19 O19 -179.9(4) . . . . no
O18 C18 C19 N20 3.6(6) . . . . no
N17 C18 C19 O19 -0.5(6) . . . . no
N17 C18 C19 N20 -177.0(4) . . . . no
N20 C21 C22 O23A -179.0(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 N10 2.749(5) . . no
O8 C6 3.097(6) . . no
O8 O13B 3.034(18) . 2_765 no
O8 N10 2.973(6) . 2_765 no
O8 C12C 3.330(15) . 2_765 no
O9 C18 3.119(6) . 1_665 no
O9 N20 3.235(5) . 1_665 no
O9 N7 2.659(5) . . no
O9 C19 3.041(5) . 1_665 no
O13A O13A 2.98(3) . 2_875 no
O13A C12A 3.28(3) . 2_875 no
O13A C21 3.388(17) . 2_766 no
O13A O19 2.82(2) . 2_766 no
O13B O13B 3.17(2) . 2_875 no
O13B C6 3.293(18) . 2_765 no
O13B C12B 2.97(3) . 2_875 no
O13B O8 3.034(18) . 2_765 no
O13B N10 3.136(16) . . no
O13C C12C 3.334(19) . 2_875 no
O13C N10 2.875(14) . . no
O13C O23A 2.776(16) . 1_664 no
O13C C22 3.192(14) . 1_664 no
O18 N20 3.145(5) . 2_646 no
O18 C21 3.220(6) . 2_646 no
O18 C1 3.384(6) . 2_756 no
O18 C4 2.978(6) . . no
O18 N7 2.936(5) . 2_756 no
O18 C24 3.351(6) . 2_756 no
O18 N20 2.727(5) . . no
O19 N17 2.670(5) . . no
O19 C11B 3.28(3) . 2_766 no
O19 N17 2.928(5) . 2_656 no
O19 C11A 3.251(5) . 2_766 no
O19 C24 3.301(6) . 2_656 no
O19 C11C 3.180(13) . 2_766 no
O19 O13A 2.82(2) . 2_766 no
O23A O13C 2.776(16) . 1_446 no
O23A C12A 3.38(2) . 1_446 no
O23A C22 3.255(10) . 2_647 no
O23B C8 3.372(10) . 2_756 no
O23B N20 2.925(8) . . no
O8 H6 2.8300 . . no
O8 H12A 2.8800 . 2_765 no
O8 H10 2.1900 . 2_765 no
O8 H10 2.3900 . . no
O8 H12F 2.5600 . 2_765 no
O9 H11D 2.4600 . . no
O9 H20A 2.4900 . 2_756 no
O9 H11F 2.3800 . . no
O9 H7 2.2600 . . no
O9 H22C 2.8800 . 2_756 no
O9 H11B 2.6000 . . no
O13A H21A 2.6400 . 2_766 no
O13A H12A 2.9100 . 2_875 no
O13B H13B 2.6400 . 2_875 no
O13B H12D 2.4000 . 2_875 no
O13C H12E 2.7400 . 2_875 no
O13C H22B 2.8400 . 1_664 no
O13C H23A 1.9100 . 1_664 no
O18 H24B 2.6500 . 2_756 no
O18 H7 2.1800 . 2_756 no
O18 H20A 2.3600 . . no
O18 H4 2.5100 . . no
O18 H20A 2.7800 . 2_646 no
O18 H21B 2.6700 . 2_646 no
O19 H21A 2.4800 . . no
O19 H17 2.2500 . . no
O19 H11E 2.8500 . 2_766 no
O19 H11F 2.8200 . 2_766 no
O19 H11B 2.5900 . 2_766 no
O19 H11D 2.6500 . 2_766 no
O19 H17 2.2000 . 2_656 no
O19 H24A 2.6300 . 2_656 no
O19 H12D 2.8500 . 2_766 no
O19 H13A 2.2800 . 2_766 no
O23A H12A 2.8200 . 1_446 no
O23A H12C 2.7600 . 1_446 no
O23A H13C 2.4600 . 1_446 no
N7 O18 2.936(5) . 2_756 no
N7 O9 2.659(5) . . no
N7 C18 3.430(6) . 2_756 no
N10 O13C 2.875(14) . . no
N10 O13B 3.136(16) . . no
N10 O8 2.749(5) . . no
N10 O8 2.973(6) . 2_765 no
N17 O19 2.670(5) . . no
N17 O19 2.928(5) . 2_656 no
N20 O23B 2.925(8) . . no
N20 O18 3.145(5) . 2_646 no
N20 O9 3.235(5) . 1_445 no
N20 O18 2.727(5) . . no
N7 H24C 2.5700 . . no
N17 H11F 2.9000 . 1_445 no
N17 H24A 2.4700 . . no
C1 O18 3.384(6) . 2_756 no
C1 C18 3.557(6) . 2_756 no
C4 O18 2.978(6) . . no
C5 C11A 3.574(8) . 1_545 no
C6 O13B 3.293(18) . 2_765 no
C6 O8 3.097(6) . . no
C8 O23B 3.372(10) . 2_756 no
C11A O19 3.251(5) . 2_766 no
C11A C5 3.574(8) . 1_565 no
C11B O19 3.28(2) . 2_766 no
C11C O19 3.180(13) . 2_766 no
C12A O13A 3.28(3) . 2_875 no
C12A O23A 3.38(2) . 1_664 no
C12B O13B 2.97(3) . 2_875 no
C12B C12B 3.43(4) . 2_875 no
C12C O13C 3.334(19) . 2_875 no
C12C O8 3.330(15) . 2_765 no
C18 N7 3.430(6) . 2_756 no
C18 C1 3.557(6) . 2_756 no
C18 O9 3.119(6) . 1_445 no
C19 O9 3.041(5) . 1_445 no
C21 O13A 3.388(17) . 2_766 no
C21 O18 3.220(6) . 2_646 no
C22 O13C 3.192(14) . 1_446 no
C22 O23A 3.255(10) . 2_647 no
C24 O19 3.301(6) . 2_656 no
C24 O18 3.351(6) . 2_756 no
C4 H24B 2.9900 . 2_756 no
C4 H12C 3.1000 . 1_445 no
C4 H12B 2.9800 . 1_445 no
C5 H11C 3.0500 . 1_545 no
C5 H11A 2.6500 . 1_545 no
C6 H12F 3.0300 . 2_765 no
C6 H11A 2.8400 . 1_545 no
C8 H6 2.9400 . . no
C12A H23A 2.6700 . 1_664 no
C12B H13B 2.2200 . 2_875 no
C12B H23A 2.6100 . 1_664 no
C18 H7 2.8700 . 2_756 no
C18 H4 2.8000 . . no
C19 H13A 3.0700 . 2_766 no
C21 H13C 2.8500 . 1_446 no
C21 H13A 3.0000 . 2_766 no
C22 H13C 2.7000 . 1_446 no
C22 H23A 3.0800 . 2_647 no
C22 H23B 2.8400 . 2_647 no
C22 H4 2.9900 . 2_646 no
C24 H17 2.6500 . . no
C24 H7 2.7700 . . no
H4 O18 2.5100 . . no
H4 C18 2.8000 . . no
H4 C22 2.9900 . 2_646 no
H4 H22C 2.3100 . 2_646 no
H5 H23B 2.5900 . 1_554 no
H5 H11A 2.4100 . 1_545 no
H5 H6 2.5900 . 2_755 no
H6 O8 2.8300 . . no
H6 C8 2.9400 . . no
H6 H5 2.5900 . 2_755 no
H7 H24C 2.5000 . . no
H7 O18 2.1800 . 2_756 no
H7 H20A 2.5600 . 2_756 no
H7 C24 2.7700 . . no
H7 C18 2.8700 . 2_756 no
H7 O9 2.2600 . . no
H10 O8 2.3900 . . no
H10 O8 2.1900 . 2_765 no
H10 H12A 2.3000 . . no
H10 H12F 2.4900 . . no
H11A C5 2.6500 . 1_565 no
H11A C6 2.8400 . 1_565 no
H11A H5 2.4100 . 1_565 no
H11B O9 2.6000 . . no
H11B O19 2.5900 . 2_766 no
H11B H24A 2.4300 . 2_766 no
H11C C5 3.0500 . 1_565 no
H11D O19 2.6500 . 2_766 no
H11D O9 2.4600 . . no
H11E H24A 2.5600 . 2_766 no
H11E O19 2.8500 . 2_766 no
H11F O9 2.3800 . . no
H11F N17 2.9000 . 1_665 no
H11F O19 2.8200 . 2_766 no
H12A H10 2.3000 . . no
H12A O13A 2.9100 . 2_875 no
H12A H23A 2.2900 . 1_664 no
H12A O8 2.8800 . 2_765 no
H12A O23A 2.8200 . 1_664 no
H12B C4 2.9800 . 1_665 no
H12B H23A 2.2100 . 1_664 no
H12C H13B 2.4300 . 2_875 no
H12C O23A 2.7600 . 1_664 no
H12C H23A 1.8000 . 1_664 no
H12C C4 3.1000 . 1_665 no
H12D O13B 2.4000 . 2_875 no
H12D H13B 1.5800 . 2_875 no
H12D O19 2.8500 . 2_766 no
H12E H13C 2.4500 . 2_875 no
H12E O13C 2.7400 . 2_875 no
H12F O8 2.5600 . 2_765 no
H12F H10 2.4900 . . no
H12F C6 3.0300 . 2_765 no
H13A C19 3.0700 . 2_766 no
H13A O19 2.2800 . 2_766 no
H13A H21A 2.1500 . 2_766 no
H13A C21 3.0000 . 2_766 no
H13B H12C 2.4300 . 2_875 no
H13B C12B 2.2200 . 2_875 no
H13B O13B 2.6400 . 2_875 no
H13B H12D 1.5800 . 2_875 no
H13B H13B 2.3000 . 2_875 no
H13C O23A 2.4600 . 1_664 no
H13C H21A 2.2100 . 1_664 no
H13C H22B 2.4700 . 1_664 no
H13C H23A 1.7500 . 1_664 no
H13C H12E 2.4500 . 2_875 no
H13C C21 2.8500 . 1_664 no
H13C C22 2.7000 . 1_664 no
H17 O19 2.2500 . . no
H17 O19 2.2000 . 2_656 no
H17 C24 2.6500 . . no
H17 H24A 2.0000 . . no
H20A O18 2.3600 . . no
H20A H22C 2.4400 . . no
H20A O9 2.4900 . 2_756 no
H20A O18 2.7800 . 2_646 no
H20A H7 2.5600 . 2_756 no
H21A O13A 2.6400 . 2_766 no
H21A H13A 2.1500 . 2_766 no
H21A H13C 2.2100 . 1_446 no
H21A O19 2.4800 . . no
H21B O18 2.6700 . 2_646 no
H22A H23B 2.2900 . 2_647 no
H22B H13C 2.4700 . 1_446 no
H22B O13C 2.8400 . 1_446 no
H22C H4 2.3100 . 2_646 no
H22C H20A 2.4400 . . no
H22C O9 2.8800 . 2_756 no
H23A O13C 1.9100 . 1_446 no
H23A C22 3.0800 . 2_647 no
H23A H12A 2.2900 . 1_446 no
H23A C12A 2.6700 . 1_446 no
H23A C12B 2.6100 . 1_446 no
H23A H13C 1.7500 . 1_446 no
H23A H12B 2.2100 . 1_446 no
H23A H12C 1.8000 . 1_446 no
H23B C22 2.8400 . 2_647 no
H23B H5 2.5900 . 1_556 no
H23B H22A 2.2900 . 2_647 no
H24A H11B 2.4300 . 2_766 no
H24A H11E 2.5600 . 2_766 no
H24A O19 2.6300 . 2_656 no
H24A N17 2.4700 . . no
H24A H17 2.0000 . . no
H24B O18 2.6500 . 2_756 no
H24B C4 2.9900 . 2_756 no
H24C N7 2.5700 . . no
H24C H7 2.5000 . . no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.2600 2.659(5) 109.00 . yes
N7 H7 O18 0.8600 2.1800 2.936(5) 146.00 2_756 yes
N10 H10 O8 0.8600 2.3900 2.749(5) 106.00 . yes
N10 H10 O8 0.8600 2.1900 2.973(6) 151.00 2_765 yes
N17 H17 O19 0.8600 2.2500 2.670(5) 110.00 . yes
N17 H17 O19 0.8600 2.2000 2.928(5) 142.00 2_656 yes
N20 H20A O18 0.8600 2.3600 2.727(5) 106.00 . yes
N20 H20A O9 0.8600 2.4900 3.308(5) 160.00 2_756 yes
C4 H4 O18 0.9300 2.5100 2.978(6) 111.00 . yes
C21 H21A O19 0.9700 2.4800 2.847(6) 102.00 . yes
C24 H24A N17 0.9600 2.4700 2.886(6) 106.00 . yes

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.078


data_srl134
_database_code_depnum_ccdc_archive 'CCDC 801213'
#TrackingRef 'compuesto6.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N,N'-Bis-[2-(2-(2-hydroxyethoxy)ethylamino)
oxalyl]-1,3-(2,4,6-trimethyl)phenylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H32 N4 O8'
_chemical_formula_weight         468.51

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_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   11.4567(6)
_cell_length_b                   12.9050(7)
_cell_length_c                   16.4558(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.828(2)
_cell_angle_gamma                90.00
_cell_volume                     2381.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_Cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Bruker APEXII area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_reflns_number            7153
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.1045
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2096
_reflns_number_gt                985
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2008)'
_computing_publication_material  
'SHELXL97 (Sheldrick, 2008) and WINGX-2003 (Farrugia, 1999)'

_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^)+(0.0936P)^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     SHELXL
_refine_ls_extinction_coef       0.061(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2096
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   0.816
_refine_ls_restrained_S_all      0.816
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani 0.30852(18) 0.31694(19) 0.08209(14) 1.000 0.0595(9) . .
O9 O Uani 0.05274(18) 0.33499(19) 0.16540(15) 1.000 0.0632(10) . .
O13 O Uani -0.1931(2) 0.1218(2) -0.04894(18) 1.000 0.0832(11) . .
O16 O Uani -0.3645(2) 0.0345(2) -0.18371(15) 1.000 0.0718(10) . .
N7 N Uani 0.28191(19) 0.3920(2) 0.20127(15) 1.000 0.0424(9) . .
N10 N Uani 0.0752(2) 0.2662(3) 0.0438(2) 1.000 0.0720(13) . .
C1 C Uani 0.3948(2) 0.4443(2) 0.22548(18) 1.000 0.0381(11) . .
C2 C Uani 0.50000 0.3872(3) 0.25000 1.000 0.0375(16) . .
C5 C Uani 0.50000 0.6029(3) 0.25000 1.000 0.0518(17) . .
C6 C Uani 0.3931(3) 0.5520(3) 0.22362(19) 1.000 0.0474(11) . .
C8 C Uani 0.2463(3) 0.3403(2) 0.1316(2) 1.000 0.0437(11) . .
C9 C Uani 0.1141(3) 0.3126(3) 0.1152(2) 1.000 0.0489(11) . .
C11 C Uani -0.0509(3) 0.2418(4) 0.0095(3) 1.000 0.111(2) . .
C12 C Uani -0.0703(3) 0.1416(4) -0.0123(3) 1.000 0.114(3) . .
C14 C Uani -0.2079(3) 0.0153(3) -0.0654(3) 1.000 0.0747(17) . .
C15 C Uani -0.3328(3) -0.0066(3) -0.1028(2) 1.000 0.0705(17) . .
C17 C Uani 0.50000 0.2712(3) 0.25000 1.000 0.0508(17) . .
C18 C Uani 0.2799(3) 0.6116(3) 0.1924(3) 1.000 0.0721(16) . .
H5 H Uiso 0.50000 0.67494 0.25000 1.000 0.0620 . .
H7 H Uiso 0.23383 0.39482 0.23507 1.000 0.0509 . .
H10 H Uiso 0.12691 0.24885 0.01505 1.000 0.0862 . .
H11A H Uiso -0.09767 0.25924 0.05050 1.000 0.1332 . .
H11B H Uiso -0.07862 0.28487 -0.03891 1.000 0.1332 . .
H12A H Uiso -0.04667 0.09839 0.03659 1.000 0.1370 . .
H12B H Uiso -0.02110 0.12293 -0.05147 1.000 0.1370 . .
H14A H Uiso -0.18463 -0.02349 -0.01413 1.000 0.0896 . .
H14B H Uiso -0.15731 -0.00612 -0.10289 1.000 0.0896 . .
H15A H Uiso -0.34537 -0.08098 -0.10488 1.000 0.0844 . .
H15B H Uiso -0.38375 0.02309 -0.06853 1.000 0.0844 . .
H16 H Uiso -0.42176 0.07579 -0.18627 1.000 0.1076 . .
H17A H Uiso 0.45134 0.24643 0.28694 0.500 0.0609 . .
H17B H Uiso 0.58010 0.24643 0.26820 0.500 0.0609 . .
H17C H Uiso 0.46856 0.24643 0.19486 0.500 0.0609 . .
H18A H Uiso 0.24437 0.58862 0.13737 1.000 0.1080 . .
H18B H Uiso 0.29781 0.68422 0.19113 1.000 0.1080 . .
H18C H Uiso 0.22537 0.60011 0.22860 1.000 0.1080 . .

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
O8 0.0400(13) 0.0866(19) 0.0546(16) -0.0171(13) 0.0160(12) -0.0073(12)
O9 0.0381(13) 0.0850(19) 0.0688(18) -0.0173(14) 0.0161(12) -0.0021(12)
O13 0.0437(15) 0.090(2) 0.111(2) -0.0289(18) 0.0041(14) -0.0165(14)
O16 0.0491(15) 0.110(2) 0.0556(17) 0.0057(15) 0.0090(12) 0.0121(13)
N7 0.0289(14) 0.0572(18) 0.0423(17) -0.0068(14) 0.0100(11) -0.0029(12)
N10 0.0307(16) 0.104(3) 0.081(2) -0.041(2) 0.0108(15) -0.0111(16)
C1 0.0302(16) 0.045(2) 0.0397(19) -0.0027(15) 0.0085(13) -0.0029(15)
C2 0.029(2) 0.045(3) 0.038(3) 0.0000 0.0054(18) 0.0000
C5 0.059(3) 0.032(3) 0.065(3) 0.0000 0.014(2) 0.0000
C6 0.0406(19) 0.052(2) 0.050(2) 0.0049(17) 0.0105(15) 0.0065(17)
C8 0.0337(17) 0.050(2) 0.048(2) -0.0002(17) 0.0095(15) 0.0011(15)
C9 0.0328(17) 0.060(2) 0.054(2) -0.0093(18) 0.0089(16) -0.0016(16)
C11 0.044(3) 0.129(4) 0.161(5) -0.082(4) 0.023(3) -0.017(3)
C12 0.048(3) 0.137(5) 0.161(5) -0.059(4) 0.029(3) -0.021(3)
C14 0.060(3) 0.087(3) 0.070(3) 0.002(2) -0.003(2) 0.006(2)
C15 0.067(3) 0.070(3) 0.073(3) 0.004(2) 0.011(2) -0.010(2)
C17 0.039(3) 0.045(3) 0.066(3) 0.0000 0.005(2) 0.0000
C18 0.053(2) 0.062(3) 0.100(3) 0.016(2) 0.013(2) 0.0177(19)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.225(4) . . yes
O9 C9 1.224(4) . . yes
O13 C12 1.435(5) . . yes
O13 C14 1.404(5) . . yes
O16 C15 1.410(4) . . yes
O16 H16 0.8400 . . no
N7 C8 1.317(4) . . yes
N7 C1 1.441(3) . . yes
N10 C9 1.313(5) . . yes
N10 C11 1.473(5) . . yes
N7 H7 0.8600 . . no
N10 H10 0.8600 . . no
C1 C2 1.400(3) . . no
C1 C6 1.390(5) . . no
C2 C17 1.497(5) . . no
C5 C6 1.379(4) . 2_655 no
C5 C6 1.379(4) . . no
C6 C18 1.505(5) . . no
C8 C9 1.525(5) . . no
C11 C12 1.348(7) . . no
C14 C15 1.465(5) . . no
C5 H5 0.9300 . . no
C11 H11A 0.9700 . . no
C11 H11B 0.9700 . . no
C12 H12A 0.9700 . . no
C12 H12B 0.9700 . . no
C14 H14A 0.9700 . . no
C14 H14B 0.9700 . . no
C15 H15A 0.9700 . . no
C15 H15B 0.9700 . . no
C17 H17A 0.9600 . . no
C17 H17B 0.9600 . . no
C17 H17C 0.9600 . . no
C17 H17A 0.9600 . 2_655 no
C17 H17B 0.9600 . 2_655 no
C17 H17C 0.9600 . 2_655 no
C18 H18A 0.9600 . . no
C18 H18B 0.9600 . . no
C18 H18C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O13 C14 108.9(3) . . . yes
C15 O16 H16 109.00 . . . no
C1 N7 C8 125.3(3) . . . yes
C9 N10 C11 124.5(3) . . . yes
C8 N7 H7 117.00 . . . no
C1 N7 H7 117.00 . . . no
C9 N10 H10 118.00 . . . no
C11 N10 H10 118.00 . . . no
N7 C1 C2 120.3(2) . . . yes
C2 C1 C6 122.7(3) . . . no
N7 C1 C6 117.0(2) . . . yes
C1 C2 C1 116.5(3) . . 2_655 no
C1 C2 C17 121.77(17) . . . no
C1 C2 C17 121.77(17) 2_655 . . no
C6 C5 C6 123.1(4) . . 2_655 no
C1 C6 C5 117.5(3) . . . no
C5 C6 C18 120.8(3) . . . no
C1 C6 C18 121.7(3) . . . no
O8 C8 C9 121.1(3) . . . yes
N7 C8 C9 113.1(3) . . . yes
O8 C8 N7 125.8(3) . . . yes
O9 C9 C8 120.8(3) . . . yes
N10 C9 C8 114.1(3) . . . yes
O9 C9 N10 125.1(3) . . . yes
N10 C11 C12 113.7(4) . . . yes
O13 C12 C11 112.1(4) . . . yes
O13 C14 C15 109.8(3) . . . yes
O16 C15 C14 111.4(3) . . . yes
C6 C5 H5 118.00 . . . no
C6 C5 H5 118.00 2_655 . . no
N10 C11 H11A 109.00 . . . no
N10 C11 H11B 109.00 . . . no
C12 C11 H11A 109.00 . . . no
C12 C11 H11B 109.00 . . . no
H11A C11 H11B 108.00 . . . no
O13 C12 H12A 109.00 . . . no
O13 C12 H12B 109.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
H12A C12 H12B 108.00 . . . no
O13 C14 H14A 110.00 . . . no
O13 C14 H14B 110.00 . . . no
C15 C14 H14A 110.00 . . . no
C15 C14 H14B 110.00 . . . no
H14A C14 H14B 108.00 . . . no
O16 C15 H15A 109.00 . . . no
O16 C15 H15B 109.00 . . . no
C14 C15 H15A 109.00 . . . no
C14 C15 H15B 109.00 . . . no
H15A C15 H15B 108.00 . . . no
C2 C17 H17A 109.00 . . . no
C2 C17 H17B 109.00 . . . no
C2 C17 H17C 109.00 . . . no
C2 C17 H17A 109.00 . . 2_655 no
C2 C17 H17B 109.00 . . 2_655 no
C2 C17 H17C 109.00 . . 2_655 no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17A C17 H17A 141.00 . . 2_655 no
H17A C17 H17B 56.00 . . 2_655 no
H17A C17 H17C 56.00 . . 2_655 no
H17B C17 H17C 109.00 . . . no
H17A C17 H17B 56.00 2_655 . . no
H17B C17 H17B 141.00 . . 2_655 no
H17B C17 H17C 56.00 . . 2_655 no
H17A C17 H17C 56.00 2_655 . . no
H17B C17 H17C 56.00 2_655 . . no
H17C C17 H17C 141.00 . . 2_655 no
H17A C17 H17B 109.00 2_655 . 2_655 no
H17A C17 H17C 109.00 2_655 . 2_655 no
H17B C17 H17C 109.00 2_655 . 2_655 no
C6 C18 H18A 109.00 . . . no
C6 C18 H18B 109.00 . . . no
C6 C18 H18C 110.00 . . . no
H18A C18 H18B 109.00 . . . no
H18A C18 H18C 109.00 . . . no
H18B C18 H18C 109.00 . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 O13 C12 C11 -176.5(4) . . . . no
C12 O13 C14 C15 180.0(3) . . . . no
C8 N7 C1 C2 -72.4(4) . . . . no
C8 N7 C1 C6 108.0(3) . . . . no
C1 N7 C8 O8 10.3(5) . . . . no
C1 N7 C8 C9 -168.1(3) . . . . no
C11 N10 C9 O9 5.6(7) . . . . no
C11 N10 C9 C8 -173.1(4) . . . . no
C9 N10 C11 C12 -127.1(5) . . . . no
N7 C1 C2 C17 1.6(3) . . . . no
N7 C1 C2 C1 -178.4(2) . . . 2_655 no
C6 C1 C2 C17 -178.8(2) . . . . no
C6 C1 C2 C1 1.2(3) . . . 2_655 no
N7 C1 C6 C5 177.3(2) . . . . no
N7 C1 C6 C18 -4.0(5) . . . . no
C2 C1 C6 C5 -2.3(4) . . . . no
C2 C1 C6 C18 176.4(3) . . . . no
C6 C5 C6 C1 1.1(4) 2_655 . . . no
C6 C5 C6 C18 -177.6(3) 2_655 . . . no
O8 C8 C9 O9 179.1(3) . . . . no
O8 C8 C9 N10 -2.2(5) . . . . no
N7 C8 C9 O9 -2.4(5) . . . . no
N7 C8 C9 N10 176.3(3) . . . . no
N10 C11 C12 O13 -177.3(3) . . . . no
O13 C14 C15 O16 69.1(4) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 N10 2.698(3) . . no
O8 C2 3.284(2) . . no
O8 C17 3.211(2) . . no
O8 N10 2.889(4) . 7_555 no
O9 C15 3.354(4) . 7_455 no
O9 C5 3.409(4) . 6_545 no
O9 O16 2.989(3) . 8_555 no
O9 N7 2.674(3) . . no
O9 O16 2.801(3) . 7_455 no
O9 C5 3.409(4) . 5_445 no
O13 O16 2.874(4) . . no
O16 O9 2.989(3) . 8_454 no
O16 O9 2.801(3) . 7_455 no
O16 O13 2.874(4) . . no
O16 N7 2.932(3) . 8_454 no
O8 H12B 2.7000 . 7_555 no
O8 H17B 2.6900 . 2_655 no
O8 H10 2.0800 . 7_555 no
O8 H17C 2.5000 . . no
O8 H10 2.3200 . . no
O8 H14A 2.6100 . 5_555 no
O9 H16 1.9800 . 7_455 no
O9 H15B 2.8900 . 7_455 no
O9 H5 2.6300 . 6_545 no
O9 H11A 2.4800 . . no
O9 H16 2.6600 . 8_555 no
O9 H7 2.2900 . . no
O9 H5 2.6300 . 5_445 no
O13 H11A 2.8400 . 7_455 no
O16 H7 2.1200 . 8_454 no
O16 H18C 2.6000 . 8_454 no
N7 O9 2.674(3) . . no
N7 O16 2.932(3) . 8_555 no
N10 O8 2.889(4) . 7_555 no
N10 O8 2.698(3) . . no
N7 H17C 2.8600 . . no
N7 H17B 2.4400 . 2_655 no
N7 H18A 2.7500 . . no
N7 H18C 2.8200 . . no
N7 H17A 2.8600 . . no
C2 O8 3.284(2) . . no
C2 O8 3.284(2) . 2_655 no
C5 O9 3.409(4) . 5_555 no
C5 O9 3.409(4) . 6_555 no
C8 C17 3.274(4) . . no
C15 O9 3.354(4) . 7_455 no
C17 C8 3.274(4) . . no
C17 O8 3.211(2) . . no
C17 C8 3.274(4) . 2_655 no
C17 O8 3.211(2) . 2_655 no
C6 H14B 3.0800 . 8_555 no
C8 H17B 2.6100 . 2_655 no
C8 H17C 2.8200 . . no
C9 H16 3.0600 . 7_455 no
C18 H7 2.9600 . . no
H5 H18B 2.3200 . . no
H5 H18B 2.3200 . 2_655 no
H5 O9 2.6300 . 5_555 no
H5 O9 2.6300 . 6_555 no
H7 O9 2.2900 . . no
H7 C18 2.9600 . . no
H7 O16 2.1200 . 8_555 no
H7 H16 2.4400 . 8_555 no
H10 O8 2.3200 . . no
H10 H12B 2.4400 . . no
H10 O8 2.0800 . 7_555 no
H11A O9 2.4800 . . no
H11A O13 2.8400 . 7_455 no
H12A H14A 2.2600 . . no
H12B H10 2.4400 . . no
H12B H14B 2.3200 . . no
H12B O8 2.7000 . 7_555 no
H14A H12A 2.2600 . . no
H14A O8 2.6100 . 5_445 no
H14B H12B 2.3200 . . no
H14B C6 3.0800 . 8_454 no
H15B O9 2.8900 . 7_455 no
H16 H16 2.4600 . 2_454 no
H16 O9 1.9800 . 7_455 no
H16 C9 3.0600 . 7_455 no
H16 O9 2.6600 . 8_454 no
H16 H7 2.4400 . 8_454 no
H17A N7 2.8600 . . no
H17B O8 2.6900 . 2_655 no
H17B N7 2.4400 . 2_655 no
H17B C8 2.6100 . 2_655 no
H17C O8 2.5000 . . no
H17C N7 2.8600 . . no
H17C C8 2.8200 . . no
H18A N7 2.7500 . . no
H18B H5 2.3200 . . no
H18C N7 2.8200 . . no
H18C O16 2.6000 . 8_555 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.2900 2.674(3) 107.00 . yes
N7 H7 O16 0.8600 2.1200 2.932(3) 157.00 8_555 yes
N10 H10 O8 0.8600 2.3200 2.698(3) 107.00 . yes
N10 H10 O8 0.8600 2.0800 2.889(4) 158.00 7_555 yes
O16 H16 O9 0.8400 1.9800 2.801(3) 167.00 7_455 yes
C11 H11A O9 0.9700 2.4800 2.862(5) 103.00 . yes
C17 H17B N7 0.9600 2.4400 2.915(3) 110.00 2_655 yes
C17 H17C O8 0.9600 2.5000 3.211(2) 131.00 . yes
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.078

_publ_section_abstract           
;
?
;

_publ_section_comment            
;
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

_publ_section_acknowledgements   
;
?
;

_publ_section_figure_captions    
;
?
;

data_17
_database_code_depnum_ccdc_archive 'CCDC 801214'
#TrackingRef 'compuesto7.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N,N-Bis[(2-(2-hydroxyethylamino)oxalyl)]-1,3-
(5-tertbuthyl-2-methoxy)phenylenediamine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H28 N4 O7'
_chemical_formula_sum            'C19 H28 N4 O7'
_chemical_formula_weight         424.45

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_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   13.066(3)
_cell_length_b                   24.384(5)
_cell_length_c                   13.303(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90
_cell_volume                     4238.4(16)
_cell_formula_units_Z            8

_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1808
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w'
_diffrn_standards_decay_%        5
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_reflns_number            11757
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0749
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3613
_reflns_number_gt                2364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'CRYSTALS (Betteridge <i>et al.</i>, 2003)'
_computing_molecular_graphics    'CAMERON (Watkin <i>et al.</i>, 1996)'
_computing_publication_material  'PLATON (Spek, 2003)'

_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^)+(0.0980P)^2^+0.2879P] 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         3613
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1858
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O8 O Uani 0.08138(14) 0.12698(8) 0.14188(16) 1.000 0.0309(7) . .
O9 O Uani -0.18364(14) 0.12993(8) 0.10454(17) 1.000 0.0319(7) . .
O13 O Uani -0.12661(16) 0.00400(9) -0.06794(19) 1.000 0.0437(9) . .
O18 O Uani 0.10112(15) 0.46044(8) 0.14855(17) 1.000 0.0342(8) . .
O19 O Uani -0.15778(15) 0.47099(8) 0.08646(17) 1.000 0.0334(8) . .
O23 O Uani -0.13506(14) 0.59765(8) 0.29729(16) 1.000 0.0312(7) . .
O24 O Uani -0.11652(14) 0.29732(7) 0.08487(16) 1.000 0.0256(7) . .
N7 N Uani -0.02901(17) 0.19942(9) 0.12156(19) 1.000 0.0219(8) . .
N10 N Uani -0.07784(17) 0.05617(9) 0.12441(19) 1.000 0.0289(9) . .
N17 N Uani -0.01732(17) 0.39328(9) 0.11477(19) 1.000 0.0248(8) . .
N20 N Uani -0.04299(17) 0.53844(9) 0.12610(19) 1.000 0.0257(8) . .
C1 C Uani 0.03351(19) 0.24622(11) 0.1313(2) 1.000 0.0195(9) . .
C2 C Uani -0.0145(2) 0.29585(10) 0.1140(2) 1.000 0.0202(9) . .
C3 C Uani 0.0383(2) 0.34487(11) 0.1275(2) 1.000 0.0212(9) . .
C4 C Uani 0.1413(2) 0.34300(11) 0.1537(2) 1.000 0.0236(9) . .
C5 C Uani 0.1911(2) 0.29303(11) 0.1675(2) 1.000 0.0216(9) . .
C6 C Uani 0.13630(19) 0.24504(11) 0.1578(2) 1.000 0.0217(9) . .
C8 C Uani -0.0039(2) 0.14609(11) 0.1283(2) 1.000 0.0215(9) . .
C9 C Uani -0.0985(2) 0.10899(11) 0.1178(2) 1.000 0.0240(10) . .
C11 C Uani -0.1546(2) 0.01296(12) 0.1138(3) 1.000 0.0357(10) . .
C12 C Uani -0.1308(2) -0.02442(12) 0.0260(3) 1.000 0.0378(13) . .
C18 C Uani 0.0147(2) 0.44564(11) 0.1268(2) 1.000 0.0237(10) . .
C19 C Uani -0.0719(2) 0.48678(12) 0.1111(2) 1.000 0.0238(10) . .
C21 C Uani -0.1143(2) 0.58411(11) 0.1194(2) 1.000 0.0285(10) . .
C22 C Uani -0.1886(2) 0.58619(12) 0.2062(2) 1.000 0.0310(10) . .
C25 C Uani -0.1269(2) 0.29439(13) -0.0226(3) 1.000 0.0376(11) . .
C26 C Uani 0.3063(2) 0.29365(11) 0.1900(3) 1.000 0.0268(10) . .
C27 C Uani 0.3284(2) 0.32858(16) 0.2816(3) 1.000 0.0474(13) . .
C28 C Uani 0.3625(3) 0.31705(17) 0.0985(3) 1.000 0.0503(14) . .
C29 C Uani 0.3458(3) 0.23568(15) 0.2076(4) 1.000 0.0656(16) . .
H4 H Uiso 0.17744 0.37554 0.16204 1.000 0.0283 . .
H6 H Uiso 0.16842 0.21157 0.16920 1.000 0.0260 . .
H7 H Uiso -0.09253 0.20594 0.10954 1.000 0.0263 . .
H10 H Uiso -0.01552 0.04660 0.13558 1.000 0.0346 . .
H11A H Uiso -0.22135 0.02949 0.10405 1.000 0.0427 . .
H11B H Uiso -0.15695 -0.00853 0.17516 1.000 0.0427 . .
H12A H Uiso -0.06559 -0.04229 0.03775 1.000 0.0454 . .
H12B H Uiso -0.18287 -0.05271 0.02208 1.000 0.0454 . .
H13 H Uiso -0.18572 0.01428 -0.08412 1.000 0.0657 . .
H17 H Uiso -0.08015 0.38929 0.09696 1.000 0.0298 . .
H20 H Uiso 0.02002 0.54506 0.14030 1.000 0.0309 . .
H21A H Uiso -0.15245 0.58119 0.05708 1.000 0.0340 . .
H21B H Uiso -0.07587 0.61814 0.11736 1.000 0.0340 . .
H22A H Uiso -0.23934 0.61446 0.19411 1.000 0.0373 . .
H22B H Uiso -0.22380 0.55131 0.21200 1.000 0.0373 . .
H23 H Uiso -0.17664 0.60875 0.34095 1.000 0.0467 . .
H25A H Uiso -0.19805 0.29549 -0.04034 1.000 0.0561 . .
H25B H Uiso -0.09723 0.26079 -0.04650 1.000 0.0561 . .
H25C H Uiso -0.09215 0.32493 -0.05284 1.000 0.0561 . .
H27A H Uiso 0.40070 0.32855 0.29469 1.000 0.0714 . .
H27B H Uiso 0.29279 0.31386 0.33863 1.000 0.0714 . .
H27C H Uiso 0.30586 0.36546 0.26950 1.000 0.0714 . .
H28A H Uiso 0.43479 0.31766 0.11160 1.000 0.0755 . .
H28C H Uiso 0.34912 0.29448 0.04087 1.000 0.0755 . .
H28D H Uiso 0.33896 0.35368 0.08574 1.000 0.0755 . .
H29A H Uiso 0.41790 0.23690 0.22152 1.000 0.0982 . .
H29B H Uiso 0.33398 0.21388 0.14863 1.000 0.0982 . .
H29C H Uiso 0.31056 0.21971 0.26371 1.000 0.0982 . .

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
O8 0.0268(11) 0.0242(11) 0.0418(15) -0.0020(10) -0.0056(10) 0.0027(8)
O9 0.0218(11) 0.0295(12) 0.0445(15) 0.0051(10) 0.0033(9) -0.0009(8)
O13 0.0337(13) 0.0468(15) 0.0507(17) -0.0061(12) -0.0031(11) 0.0019(10)
O18 0.0267(12) 0.0265(12) 0.0495(16) -0.0019(10) -0.0029(10) -0.0001(8)
O19 0.0301(12) 0.0273(12) 0.0427(15) -0.0013(10) -0.0056(10) 0.0017(8)
O23 0.0262(11) 0.0345(12) 0.0328(14) -0.0064(10) 0.0020(9) 0.0069(9)
O24 0.0197(10) 0.0280(12) 0.0292(14) 0.0011(9) -0.0010(9) 0.0029(8)
N7 0.0186(12) 0.0205(13) 0.0265(16) 0.0006(10) 0.0005(10) 0.0006(9)
N10 0.0279(14) 0.0222(14) 0.0365(17) -0.0033(12) 0.0021(12) -0.0015(10)
N17 0.0222(12) 0.0205(13) 0.0317(16) 0.0001(11) -0.0020(11) 0.0026(9)
N20 0.0232(13) 0.0237(13) 0.0302(16) 0.0007(11) 0.0015(11) 0.0015(10)
C1 0.0215(14) 0.0203(15) 0.0166(16) -0.0004(12) 0.0036(12) -0.0011(11)
C2 0.0162(14) 0.0264(16) 0.0179(17) 0.0009(12) 0.0024(12) 0.0015(11)
C3 0.0239(15) 0.0192(15) 0.0204(17) 0.0023(12) 0.0037(12) 0.0035(11)
C4 0.0226(15) 0.0255(16) 0.0228(18) 0.0014(13) 0.0020(12) -0.0021(11)
C5 0.0224(15) 0.0268(16) 0.0157(17) 0.0017(12) 0.0002(12) 0.0006(11)
C6 0.0227(15) 0.0208(15) 0.0215(17) 0.0011(13) 0.0012(12) 0.0038(11)
C8 0.0264(16) 0.0220(15) 0.0160(17) 0.0004(13) 0.0023(12) 0.0006(12)
C9 0.0265(16) 0.0225(16) 0.0230(18) 0.0008(13) 0.0035(13) 0.0011(12)
C11 0.0329(17) 0.0261(17) 0.048(2) -0.0009(16) 0.0070(15) -0.0079(13)
C12 0.0305(18) 0.0269(17) 0.056(3) -0.0080(17) -0.0011(16) -0.0007(13)
C18 0.0276(17) 0.0223(16) 0.0211(18) 0.0002(13) 0.0021(13) 0.0010(12)
C19 0.0259(16) 0.0254(16) 0.0201(18) -0.0005(13) 0.0016(13) -0.0008(12)
C21 0.0304(16) 0.0212(15) 0.034(2) 0.0005(14) 0.0025(14) 0.0046(12)
C22 0.0267(16) 0.0284(16) 0.038(2) -0.0007(15) -0.0041(15) 0.0028(12)
C25 0.0377(19) 0.044(2) 0.031(2) 0.0040(16) -0.0130(16) 0.0013(14)
C26 0.0210(15) 0.0293(17) 0.030(2) 0.0029(14) -0.0007(13) -0.0008(11)
C27 0.0293(18) 0.071(3) 0.042(2) -0.0109(19) -0.0060(16) -0.0042(16)
C28 0.0310(19) 0.081(3) 0.039(2) 0.005(2) 0.0055(16) -0.0021(18)
C29 0.0297(19) 0.047(2) 0.120(4) 0.016(2) -0.026(2) 0.0055(15)

#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C8 1.221(3) . . yes
O9 C9 1.237(3) . . yes
O13 C12 1.430(5) . . yes
O18 C18 1.220(3) . . yes
O19 C19 1.231(3) . . yes
O23 C22 1.427(3) . . yes
O24 C2 1.389(3) . . yes
O24 C25 1.438(5) . . yes
O13 H13 0.8400 . . no
O23 H23 0.8400 . . no
N7 C8 1.344(3) . . yes
N7 C1 1.409(3) . . yes
N10 C11 1.462(4) . . yes
N10 C9 1.319(3) . . yes
N17 C3 1.397(3) . . yes
N17 C18 1.353(3) . . yes
N20 C19 1.330(4) . . yes
N20 C21 1.455(3) . . yes
N7 H7 0.8600 . . no
N10 H10 0.8600 . . no
N17 H17 0.8600 . . no
N20 H20 0.8600 . . no
C1 C2 1.382(4) . . no
C1 C6 1.389(4) . . no
C2 C3 1.392(4) . . no
C3 C4 1.391(4) . . no
C4 C5 1.394(4) . . no
C5 C26 1.535(4) . . no
C5 C6 1.378(4) . . no
C8 C9 1.538(4) . . no
C11 C12 1.514(5) . . no
C18 C19 1.527(4) . . no
C21 C22 1.509(4) . . no
C26 C29 1.523(5) . . no
C26 C27 1.515(5) . . no
C26 C28 1.532(5) . . no
C4 H4 0.9300 . . no
C6 H6 0.9300 . . no
C11 H11A 0.9700 . . no
C11 H11B 0.9700 . . no
C12 H12A 0.9700 . . no
C12 H12B 0.9700 . . no
C21 H21A 0.9700 . . no
C21 H21B 0.9700 . . no
C22 H22A 0.9700 . . no
C22 H22B 0.9700 . . no
C25 H25A 0.9600 . . no
C25 H25B 0.9600 . . no
C25 H25C 0.9600 . . no
C27 H27A 0.9600 . . no
C27 H27B 0.9600 . . no
C27 H27C 0.9600 . . no
C28 H28A 0.9600 . . no
C28 H28C 0.9600 . . no
C28 H28D 0.9600 . . no
C29 H29A 0.9600 . . no
C29 H29B 0.9600 . . no
C29 H29C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O24 C25 111.5(2) . . . yes
C12 O13 H13 109.00 . . . no
C22 O23 H23 109.00 . . . no
C1 N7 C8 129.5(2) . . . yes
C9 N10 C11 123.9(2) . . . yes
C3 N17 C18 128.5(2) . . . yes
C19 N20 C21 122.3(2) . . . yes
C8 N7 H7 115.00 . . . no
C1 N7 H7 115.00 . . . no
C9 N10 H10 118.00 . . . no
C11 N10 H10 118.00 . . . no
C3 N17 H17 116.00 . . . no
C18 N17 H17 116.00 . . . no
C21 N20 H20 119.00 . . . no
C19 N20 H20 119.00 . . . no
N7 C1 C6 124.6(2) . . . yes
N7 C1 C2 115.5(2) . . . yes
C2 C1 C6 120.0(2) . . . no
O24 C2 C1 120.3(2) . . . yes
O24 C2 C3 119.3(2) . . . yes
C1 C2 C3 120.4(2) . . . no
N17 C3 C4 124.2(2) . . . yes
C2 C3 C4 118.9(2) . . . no
N17 C3 C2 116.9(2) . . . yes
C3 C4 C5 120.9(2) . . . no
C4 C5 C6 119.2(2) . . . no
C4 C5 C26 118.4(2) . . . no
C6 C5 C26 122.4(2) . . . no
C1 C6 C5 120.6(2) . . . no
N7 C8 C9 111.5(2) . . . yes
O8 C8 N7 127.0(3) . . . yes
O8 C8 C9 121.5(2) . . . yes
O9 C9 N10 126.6(3) . . . yes
O9 C9 C8 119.5(2) . . . yes
N10 C9 C8 113.8(2) . . . yes
N10 C11 C12 111.6(2) . . . yes
O13 C12 C11 113.0(2) . . . yes
O18 C18 C19 121.6(2) . . . yes
N17 C18 C19 112.0(2) . . . yes
O18 C18 N17 126.4(3) . . . yes
N20 C19 C18 113.0(2) . . . yes
O19 C19 N20 126.5(3) . . . yes
O19 C19 C18 120.4(3) . . . yes
N20 C21 C22 113.0(2) . . . yes
O23 C22 C21 109.9(2) . . . yes
C5 C26 C29 110.7(2) . . . no
C5 C26 C28 108.6(3) . . . no
C28 C26 C29 107.8(3) . . . no
C27 C26 C28 109.8(3) . . . no
C27 C26 C29 109.5(3) . . . no
C5 C26 C27 110.5(2) . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
N10 C11 H11A 109.00 . . . no
N10 C11 H11B 109.00 . . . no
C12 C11 H11A 109.00 . . . no
C12 C11 H11B 109.00 . . . no
H11A C11 H11B 108.00 . . . no
O13 C12 H12A 109.00 . . . no
O13 C12 H12B 109.00 . . . no
C11 C12 H12A 109.00 . . . no
C11 C12 H12B 109.00 . . . no
H12A C12 H12B 108.00 . . . no
N20 C21 H21A 109.00 . . . no
N20 C21 H21B 109.00 . . . no
C22 C21 H21A 109.00 . . . no
C22 C21 H21B 109.00 . . . no
H21A C21 H21B 108.00 . . . no
O23 C22 H22A 110.00 . . . no
O23 C22 H22B 110.00 . . . no
C21 C22 H22A 110.00 . . . no
C21 C22 H22B 110.00 . . . no
H22A C22 H22B 108.00 . . . no
O24 C25 H25A 110.00 . . . no
O24 C25 H25B 109.00 . . . no
O24 C25 H25C 109.00 . . . no
H25A C25 H25B 109.00 . . . no
H25A C25 H25C 109.00 . . . no
H25B C25 H25C 109.00 . . . no
C26 C27 H27A 109.00 . . . no
C26 C27 H27B 109.00 . . . no
C26 C27 H27C 109.00 . . . no
H27A C27 H27B 109.00 . . . no
H27A C27 H27C 109.00 . . . no
H27B C27 H27C 110.00 . . . no
C26 C28 H28A 109.00 . . . no
C26 C28 H28C 110.00 . . . no
C26 C28 H28D 109.00 . . . no
H28A C28 H28C 109.00 . . . no
H28A C28 H28D 109.00 . . . no
H28C C28 H28D 110.00 . . . no
C26 C29 H29A 109.00 . . . no
C26 C29 H29B 109.00 . . . no
C26 C29 H29C 109.00 . . . no
H29A C29 H29B 109.00 . . . no
H29A C29 H29C 109.00 . . . no
H29B C29 H29C 109.00 . . . no

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
C25 O24 C2 C1 -88.6(3) . . . . no
C25 O24 C2 C3 92.7(3) . . . . no
C8 N7 C1 C2 176.1(3) . . . . no
C8 N7 C1 C6 -4.9(5) . . . . no
C1 N7 C8 O8 -2.3(5) . . . . no
C1 N7 C8 C9 177.1(3) . . . . no
C11 N10 C9 O9 1.9(5) . . . . no
C11 N10 C9 C8 -178.1(3) . . . . no
C9 N10 C11 C12 119.0(3) . . . . no
C18 N17 C3 C2 177.6(3) . . . . no
C18 N17 C3 C4 -1.6(5) . . . . no
C3 N17 C18 O18 2.5(5) . . . . no
C3 N17 C18 C19 -176.8(3) . . . . no
C21 N20 C19 O19 3.1(4) . . . . no
C21 N20 C19 C18 -177.3(2) . . . . no
C19 N20 C21 C22 71.7(3) . . . . no
N7 C1 C2 O24 -2.7(4) . . . . no
N7 C1 C2 C3 176.1(2) . . . . no
C6 C1 C2 O24 178.3(2) . . . . no
C6 C1 C2 C3 -3.0(4) . . . . no
N7 C1 C6 C5 -178.7(3) . . . . no
C2 C1 C6 C5 0.3(4) . . . . no
O24 C2 C3 N17 2.7(4) . . . . no
O24 C2 C3 C4 -178.1(2) . . . . no
C1 C2 C3 N17 -176.0(2) . . . . no
C1 C2 C3 C4 3.2(4) . . . . no
N17 C3 C4 C5 178.4(3) . . . . no
C2 C3 C4 C5 -0.7(4) . . . . no
C3 C4 C5 C6 -1.9(4) . . . . no
C3 C4 C5 C26 176.3(3) . . . . no
C4 C5 C6 C1 2.1(4) . . . . no
C26 C5 C6 C1 -176.0(3) . . . . no
C4 C5 C26 C27 55.9(4) . . . . no
C4 C5 C26 C28 -64.6(4) . . . . no
C4 C5 C26 C29 177.3(3) . . . . no
C6 C5 C26 C27 -126.0(3) . . . . no
C6 C5 C26 C28 113.6(3) . . . . no
C6 C5 C26 C29 -4.6(5) . . . . no
O8 C8 C9 O9 179.7(3) . . . . no
O8 C8 C9 N10 -0.3(4) . . . . no
N7 C8 C9 O9 0.3(4) . . . . no
N7 C8 C9 N10 -179.7(2) . . . . no
N10 C11 C12 O13 -59.5(3) . . . . no
O18 C18 C19 O19 178.0(3) . . . . no
O18 C18 C19 N20 -1.6(4) . . . . no
N17 C18 C19 O19 -2.7(4) . . . . no
N17 C18 C19 N20 177.7(2) . . . . no
N20 C21 C22 O23 66.2(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O8 N10 2.714(3) . . no
O8 C6 2.974(3) . . no
O8 C9 3.235(3) . 2_555 no
O8 C12 3.415(4) . 3_555 no
O8 C8 3.254(3) . 2_555 no
O8 C22 3.279(3) . 5_545 no
O9 N7 2.647(3) . . no
O9 C25 3.274(4) . 7_455 no
O9 O23 2.817(3) . 6_445 no
O9 C22 3.204(3) . 6_445 no
O13 O19 2.893(3) . 7_455 no
O13 N10 2.928(4) . . no
O13 N10 3.139(3) . 3_555 no
O18 C19 3.284(4) . 2_555 no
O18 C18 3.369(4) . 2_555 no
O18 N20 2.693(3) . . no
O18 C4 2.912(3) . . no
O19 O13 2.893(3) . 7_455 no
O19 N17 2.665(3) . . no
O19 C22 3.254(4) . . no
O19 C12 3.401(4) . 7_455 no
O23 O9 2.817(3) . 6_455 no
O23 N20 2.922(3) . 2_555 no
O23 N20 2.953(3) . . no
O24 C27 3.377(4) . 2_555 no
O24 N17 2.704(3) . . no
O24 N7 2.692(3) . . no
O8 H22A 2.4600 . 5_545 no
O8 H10 2.3300 . . no
O8 H6 2.3800 . . no
O9 H7 2.2000 . . no
O9 H25A 2.5300 . 7_455 no
O9 H22A 2.8900 . 6_445 no
O9 H11A 2.5000 . . no
O9 H23 2.0300 . 6_445 no
O13 H10 2.4000 . 3_555 no
O13 H12A 2.7100 . 3_555 no
O18 H4 2.3000 . . no
O18 H20 2.3200 . . no
O19 H22B 2.7100 . . no
O19 H21A 2.7200 . . no
O19 H13 2.0800 . 7_455 no
O19 H17 2.2400 . . no
O23 H20 2.1400 . 2_555 no
O23 H11A 2.8300 . 6_455 no
O23 H25C 2.8000 . 4_565 no
O24 H7 2.2700 . . no
O24 H17 2.3000 . . no
O24 H27B 2.5500 . 2_555 no
N7 O9 2.647(3) . . no
N7 O24 2.692(3) . . no
N7 C25 3.268(4) . . no
N7 C6 3.438(4) . 2_555 no
N10 O13 2.928(4) . . no
N10 O8 2.714(3) . . no
N10 O13 3.139(3) . 3_555 no
N17 O24 2.704(3) . . no
N17 C25 3.347(4) . . no
N17 O19 2.665(3) . . no
N20 O23 2.953(3) . . no
N20 C18 3.407(4) . 3_565 no
N20 O18 2.693(3) . . no
N20 O23 2.922(3) . 2_555 no
N7 H25B 2.8300 . . no
N10 H12A 2.8800 . 3_555 no
C1 C1 3.277(4) . 2_555 no
C1 C6 3.577(4) . 2_555 no
C3 C3 3.409(4) . 2_555 no
C4 O18 2.912(3) . . no
C6 O8 2.974(3) . . no
C6 C1 3.577(4) . 2_555 no
C6 N7 3.438(4) . 2_555 no
C8 O8 3.254(3) . 2_555 no
C8 C8 3.240(4) . 2_555 no
C9 O8 3.235(3) . 2_555 no
C12 O19 3.401(4) . 7_455 no
C12 O8 3.415(4) . 3_555 no
C18 O18 3.369(4) . 2_555 no
C18 C18 3.300(4) . 2_555 no
C18 N20 3.407(4) . 3_565 no
C18 C21 3.598(4) . 3_565 no
C19 O18 3.284(4) . 2_555 no
C19 C19 3.561(4) . 3_565 no
C21 C18 3.598(4) . 3_565 no
C22 O9 3.204(3) . 6_455 no
C22 O19 3.254(4) . . no
C22 O8 3.279(3) . 5_455 no
C25 N17 3.347(4) . . no
C25 O9 3.274(4) . 7_455 no
C25 N7 3.268(4) . . no
C27 O24 3.377(4) . 2_555 no
C1 H25B 2.9400 . . no
C1 H28C 2.9300 . 7_555 no
C3 H25C 2.9800 . . no
C4 H28D 2.7500 . . no
C4 H27C 2.7000 . . no
C6 H29C 2.7500 . . no
C6 H29B 2.7000 . . no
C6 H28C 2.8200 . 7_555 no
C8 H6 2.8100 . . no
C9 H23 2.9900 . 6_445 no
C11 H22B 2.9600 . 6_445 no
C12 H10 2.9300 . 3_555 no
C18 H4 2.7700 . . no
C19 H22B 2.8700 . . no
C25 H17 2.8700 . . no
C25 H23 3.0500 . 4_564 no
C25 H29C 2.9800 . 8_454 no
C25 H7 2.8200 . . no
C27 H4 2.7800 . . no
C28 H4 2.9300 . . no
C29 H6 2.4500 . . no
H4 O18 2.3000 . . no
H4 C18 2.7700 . . no
H4 C27 2.7800 . . no
H4 C28 2.9300 . . no
H4 H27C 2.2200 . . no
H4 H28D 2.4000 . . no
H6 O8 2.3800 . . no
H6 C8 2.8100 . . no
H6 C29 2.4500 . . no
H6 H29B 2.1800 . . no
H6 H29C 2.2500 . . no
H7 O9 2.2000 . . no
H7 O24 2.2700 . . no
H7 C25 2.8200 . . no
H7 H25B 2.4700 . . no
H10 O8 2.3300 . . no
H10 O13 2.4000 . 3_555 no
H10 C12 2.9300 . 3_555 no
H10 H12A 2.5400 . 3_555 no
H11A O9 2.5000 . . no
H11A H13 2.5700 . . no
H11A O23 2.8300 . 6_445 no
H11A H23 2.4600 . 6_445 no
H12A O13 2.7100 . 3_555 no
H12A N10 2.8800 . 3_555 no
H12A H10 2.5400 . 3_555 no
H12B H28D 2.4500 . 5_445 no
H12B H21A 2.4900 . 7_455 no
H13 H11A 2.5700 . . no
H13 O19 2.0800 . 7_455 no
H17 O19 2.2400 . . no
H17 O24 2.3000 . . no
H17 C25 2.8700 . . no
H17 H25C 2.5400 . . no
H20 O18 2.3200 . . no
H20 O23 2.1400 . 2_555 no
H20 H23 2.5800 . 2_555 no
H21A O19 2.7200 . . no
H21A H12B 2.4900 . 7_455 no
H22A O8 2.4600 . 5_455 no
H22A O9 2.8900 . 6_455 no
H22B O19 2.7100 . . no
H22B C19 2.8700 . . no
H22B C11 2.9600 . 6_455 no
H23 H20 2.5800 . 2_555 no
H23 C25 3.0500 . 4_565 no
H23 H25C 2.4100 . 4_565 no
H23 O9 2.0300 . 6_455 no
H23 C9 2.9900 . 6_455 no
H23 H11A 2.4600 . 6_455 no
H25A O9 2.5300 . 7_455 no
H25B N7 2.8300 . . no
H25B C1 2.9400 . . no
H25B H7 2.4700 . . no
H25C C3 2.9800 . . no
H25C H17 2.5400 . . no
H25C O23 2.8000 . 4_564 no
H25C H23 2.4100 . 4_564 no
H27A H28A 2.4900 . . no
H27A H29A 2.4500 . . no
H27A H28A 2.5000 . 2_655 no
H27B H29C 2.5100 . . no
H27B O24 2.5500 . 2_555 no
H27C C4 2.7000 . . no
H27C H4 2.2200 . . no
H27C H28D 2.5000 . . no
H28A H27A 2.4900 . . no
H28A H29A 2.4600 . . no
H28A H27A 2.5000 . 2_655 no
H28C H29B 2.4400 . . no
H28C C1 2.9300 . 7_555 no
H28C C6 2.8200 . 7_555 no
H28D C4 2.7500 . . no
H28D H4 2.4000 . . no
H28D H27C 2.5000 . . no
H28D H12B 2.4500 . 5_555 no
H29A H27A 2.4500 . . no
H29A H28A 2.4600 . . no
H29A H29A 2.2800 . 2_655 no
H29B C6 2.7000 . . no
H29B H6 2.1800 . . no
H29B H28C 2.4400 . . no
H29C C6 2.7500 . . no
H29C H6 2.2500 . . no
H29C H27B 2.5100 . . no
H29C C25 2.9800 . 8_555 no

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
_geom_hbond_publ_flag
#
#D H A D - H H...A D...A D - H...A symm(A)
#
N7 H7 O9 0.8600 2.2000 2.647(3) 112.00 . yes
N7 H7 O24 0.8600 2.2700 2.692(3) 110.00 . yes
N10 H10 O8 0.8600 2.3300 2.714(3) 107.00 . yes
N10 H10 O13 0.8600 2.4000 3.139(3) 144.00 3_555 yes
O13 H13 O19 0.8400 2.0800 2.893(3) 164.00 7_455 yes
N17 H17 O19 0.8600 2.2400 2.665(3) 110.00 . yes
N17 H17 O24 0.8600 2.3000 2.704(3) 109.00 . yes
N20 H20 O18 0.8600 2.3200 2.693(3) 106.00 . yes
N20 H20 O23 0.8600 2.1400 2.922(3) 150.00 2_555 yes
O23 H23 O9 0.8400 2.0300 2.817(3) 156.00 6_455 yes
C4 H4 O18 0.9300 2.3000 2.912(3) 123.00 . yes
C6 H6 O8 0.9300 2.3800 2.974(3) 121.00 . yes
C11 H11A O9 0.9700 2.5000 2.880(4) 103.00 . yes
C22 H22A O8 0.9700 2.4600 3.279(3) 142.00 5_455 yes
C25 H25A O9 0.9600 2.5300 3.274(4) 134.00 7_455 yes
C27 H27B O24 0.9600 2.5500 3.377(4) 144.00 2_555 yes

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.146