# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_108_11a
_database_code_depnum_ccdc_archive 'CCDC 1477536'
_audit_update_record             
;
2016-04-29 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N2 O4'
_chemical_formula_sum            'C22 H24 N2 O4'
_chemical_formula_weight         380.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   9.0291(1)
_cell_length_b                   14.3287(3)
_cell_length_c                   14.8824(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1925.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7898
_cell_measurement_theta_min      2.9668
_cell_measurement_theta_max      66.3886

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_min  0.87487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scan'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10532
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         66.50
_reflns_number_total             3387
_reflns_number_gt                3344
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.3184P] where P=(Fo²+2Fc²)/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       0.0052(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_number_reflns         3387
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0589
_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
_chemical_absolute_configuration ad

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24826(8) 0.24601(5) 0.20151(5) 0.02045(17) Uani 1 1 d . . .
O2 O 0.00888(9) 0.27533(6) 0.01784(5) 0.0266(2) Uani 1 1 d . . .
O3 O 0.24781(8) 0.40192(5) 0.23686(5) 0.02067(18) Uani 1 1 d . . .
O4 O 0.34292(10) 0.53684(6) 0.28983(6) 0.0290(2) Uani 1 1 d . . .
N1 N 0.20447(10) 0.34703(7) 0.08909(6) 0.0197(2) Uani 1 1 d . . .
N2 N 0.47671(11) 0.43919(7) 0.19718(7) 0.0226(2) Uani 1 1 d . . .
C1 C 0.09935(12) 0.28044(8) 0.07811(8) 0.0196(2) Uani 1 1 d . . .
C2 C 0.28987(12) 0.33329(8) 0.17031(7) 0.0187(2) Uani 1 1 d . . .
C3 C 0.11614(12) 0.21388(8) 0.15662(7) 0.0185(2) Uani 1 1 d . . .
H3 H 0.0293 0.2207 0.1978 0.022 Uiso 1 1 calc R . .
C4 C 0.13383(12) 0.11304(8) 0.13112(7) 0.0192(2) Uani 1 1 d . . .
C5 C 0.26310(13) 0.08290(8) 0.08890(8) 0.0230(2) Uani 1 1 d . . .
H5 H 0.3374 0.1267 0.0727 0.028 Uiso 1 1 calc R . .
C6 C 0.28306(13) -0.01123(9) 0.07053(8) 0.0259(3) Uani 1 1 d . . .
H6 H 0.3716 -0.0318 0.0423 0.031 Uiso 1 1 calc R . .
C7 C 0.17423(14) -0.07529(9) 0.09321(8) 0.0265(3) Uani 1 1 d . . .
H7 H 0.1887 -0.1397 0.0811 0.032 Uiso 1 1 calc R . .
C8 C 0.04467(14) -0.04538(9) 0.13343(8) 0.0251(3) Uani 1 1 d . . .
H8 H -0.0304 -0.0893 0.1481 0.030 Uiso 1 1 calc R . .
C9 C 0.02386(13) 0.04879(8) 0.15244(8) 0.0216(2) Uani 1 1 d . . .
H9 H -0.0654 0.0692 0.1800 0.026 Uiso 1 1 calc R . .
C10 C 0.22441(14) 0.42366(8) 0.02584(8) 0.0237(3) Uani 1 1 d . . .
H10A H 0.1881 0.4033 -0.0338 0.028 Uiso 1 1 calc R . .
H10B H 0.3318 0.4363 0.0200 0.028 Uiso 1 1 calc R . .
C11 C 0.14737(13) 0.51393(8) 0.05026(7) 0.0213(2) Uani 1 1 d . . .
C12 C 0.03264(13) 0.51989(8) 0.11205(8) 0.0232(2) Uani 1 1 d . . .
H12 H 0.0034 0.4659 0.1446 0.028 Uiso 1 1 calc R . .
C13 C -0.03983(14) 0.60407(9) 0.12666(8) 0.0263(3) Uani 1 1 d . . .
H13 H -0.1184 0.6072 0.1690 0.032 Uiso 1 1 calc R . .
C14 C 0.00166(16) 0.68322(9) 0.07998(9) 0.0326(3) Uani 1 1 d . . .
H14 H -0.0478 0.7408 0.0902 0.039 Uiso 1 1 calc R . .
C15 C 0.11564(18) 0.67792(9) 0.01835(9) 0.0369(3) Uani 1 1 d . . .
H15 H 0.1444 0.7320 -0.0142 0.044 Uiso 1 1 calc R . .
C16 C 0.18824(16) 0.59421(9) 0.00374(8) 0.0310(3) Uani 1 1 d . . .
H16 H 0.2669 0.5915 -0.0385 0.037 Uiso 1 1 calc R . .
C17 C 0.35873(12) 0.46718(8) 0.24543(8) 0.0211(2) Uani 1 1 d . . .
C18 C 0.45939(12) 0.34589(8) 0.15936(8) 0.0205(2) Uani 1 1 d . . .
H18 H 0.4843 0.3477 0.0939 0.025 Uiso 1 1 calc R . .
C19 C 0.55124(12) 0.26900(8) 0.20493(9) 0.0250(3) Uani 1 1 d . . .
H19 H 0.5138 0.2079 0.1816 0.030 Uiso 1 1 calc R . .
C20 C 0.53331(15) 0.26690(9) 0.30664(9) 0.0316(3) Uani 1 1 d . . .
H20A H 0.4279 0.2625 0.3218 0.047 Uiso 1 1 calc R . .
H20B H 0.5747 0.3242 0.3325 0.047 Uiso 1 1 calc R . .
H20C H 0.5858 0.2127 0.3311 0.047 Uiso 1 1 calc R . .
C21 C 0.71502(14) 0.27549(10) 0.17897(11) 0.0353(3) Uani 1 1 d . . .
H21A H 0.7241 0.2764 0.1134 0.053 Uiso 1 1 calc R . .
H21B H 0.7682 0.2214 0.2030 0.053 Uiso 1 1 calc R . .
H21C H 0.7575 0.3328 0.2039 0.053 Uiso 1 1 calc R . .
C22 C 0.60645(14) 0.49801(9) 0.18523(9) 0.0285(3) Uani 1 1 d . . .
H22A H 0.5805 0.5630 0.1984 0.043 Uiso 1 1 calc R . .
H22B H 0.6414 0.4931 0.1231 0.043 Uiso 1 1 calc R . .
H22C H 0.6850 0.4775 0.2262 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3858(14) . ?
O1 C3 1.4427(13) . ?
O2 C1 1.2153(14) . ?
O3 C17 1.3761(14) . ?
O3 C2 1.4465(13) . ?
O4 C17 1.2056(14) . ?
N1 C1 1.3557(15) . ?
N1 C2 1.4472(15) . ?
N1 C10 1.4575(14) . ?
N2 C17 1.3459(15) . ?
N2 C22 1.4540(15) . ?
N2 C18 1.4589(14) . ?
C1 C3 1.5158(16) . ?
C2 C18 1.5498(16) . ?
C3 C4 1.5024(16) . ?
C4 C9 1.3907(16) . ?
C4 C5 1.3942(16) . ?
C5 C6 1.3880(17) . ?
C6 C7 1.3863(18) . ?
C7 C8 1.3822(18) . ?
C8 C9 1.3915(17) . ?
C10 C11 1.5129(16) . ?
C11 C12 1.3878(17) . ?
C11 C16 1.3924(17) . ?
C12 C13 1.3894(17) . ?
C13 C14 1.3818(19) . ?
C14 C15 1.381(2) . ?
C15 C16 1.384(2) . ?
C18 C19 1.5366(16) . ?
C19 C20 1.5227(18) . ?
C19 C21 1.5313(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 110.91(8) . . ?
C17 O3 C2 109.53(8) . . ?
C1 N1 C2 112.21(9) . . ?
C1 N1 C10 122.61(10) . . ?
C2 N1 C10 125.18(9) . . ?
C17 N2 C22 122.02(9) . . ?
C17 N2 C18 113.21(9) . . ?
C22 N2 C18 124.77(10) . . ?
O2 C1 N1 127.00(11) . . ?
O2 C1 C3 126.74(10) . . ?
N1 C1 C3 106.25(9) . . ?
O1 C2 O3 108.23(8) . . ?
O1 C2 N1 104.96(9) . . ?
O3 C2 N1 109.85(9) . . ?
O1 C2 C18 114.08(9) . . ?
O3 C2 C18 104.60(9) . . ?
N1 C2 C18 115.00(9) . . ?
O1 C3 C4 109.63(9) . . ?
O1 C3 C1 103.82(9) . . ?
C4 C3 C1 114.90(9) . . ?
C9 C4 C5 119.71(10) . . ?
C9 C4 C3 120.21(10) . . ?
C5 C4 C3 120.05(10) . . ?
C6 C5 C4 119.90(11) . . ?
C7 C6 C5 120.22(11) . . ?
C8 C7 C6 120.01(11) . . ?
C7 C8 C9 120.20(11) . . ?
C4 C9 C8 119.94(11) . . ?
N1 C10 C11 115.60(9) . . ?
C12 C11 C16 118.45(11) . . ?
C12 C11 C10 123.71(10) . . ?
C16 C11 C10 117.71(10) . . ?
C11 C12 C13 120.57(11) . . ?
C14 C13 C12 120.41(12) . . ?
C15 C14 C13 119.40(12) . . ?
C14 C15 C16 120.34(12) . . ?
C15 C16 C11 120.82(12) . . ?
O4 C17 N2 129.26(11) . . ?
O4 C17 O3 121.82(10) . . ?
N2 C17 O3 108.91(9) . . ?
N2 C18 C19 115.39(9) . . ?
N2 C18 C2 99.91(9) . . ?
C19 C18 C2 113.77(10) . . ?
C20 C19 C21 110.77(11) . . ?
C20 C19 C18 113.30(10) . . ?
C21 C19 C18 111.49(10) . . ?

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
C2 N1 C1 O2 177.85(11) . . . . ?
C10 N1 C1 O2 -1.13(18) . . . . ?
C2 N1 C1 C3 -1.64(12) . . . . ?
C10 N1 C1 C3 179.37(9) . . . . ?
C3 O1 C2 O3 103.38(9) . . . . ?
C3 O1 C2 N1 -13.89(11) . . . . ?
C3 O1 C2 C18 -140.65(9) . . . . ?
C17 O3 C2 O1 138.93(9) . . . . ?
C17 O3 C2 N1 -107.00(10) . . . . ?
C17 O3 C2 C18 16.93(11) . . . . ?
C1 N1 C2 O1 9.55(12) . . . . ?
C10 N1 C2 O1 -171.50(9) . . . . ?
C1 N1 C2 O3 -106.60(10) . . . . ?
C10 N1 C2 O3 72.35(13) . . . . ?
C1 N1 C2 C18 135.75(10) . . . . ?
C10 N1 C2 C18 -45.30(14) . . . . ?
C2 O1 C3 C4 136.15(9) . . . . ?
C2 O1 C3 C1 12.91(11) . . . . ?
O2 C1 C3 O1 173.96(11) . . . . ?
N1 C1 C3 O1 -6.55(11) . . . . ?
O2 C1 C3 C4 54.25(15) . . . . ?
N1 C1 C3 C4 -126.26(10) . . . . ?
O1 C3 C4 C9 130.34(11) . . . . ?
C1 C3 C4 C9 -113.22(12) . . . . ?
O1 C3 C4 C5 -47.30(13) . . . . ?
C1 C3 C4 C5 69.14(14) . . . . ?
C9 C4 C5 C6 -1.69(17) . . . . ?
C3 C4 C5 C6 175.96(11) . . . . ?
C4 C5 C6 C7 0.65(18) . . . . ?
C5 C6 C7 C8 0.66(18) . . . . ?
C6 C7 C8 C9 -0.91(18) . . . . ?
C5 C4 C9 C8 1.45(17) . . . . ?
C3 C4 C9 C8 -176.20(11) . . . . ?
C7 C8 C9 C4 -0.14(18) . . . . ?
C1 N1 C10 C11 95.73(13) . . . . ?
C2 N1 C10 C11 -83.12(13) . . . . ?
N1 C10 C11 C12 -17.95(16) . . . . ?
N1 C10 C11 C16 166.21(11) . . . . ?
C16 C11 C12 C13 0.26(17) . . . . ?
C10 C11 C12 C13 -175.55(11) . . . . ?
C11 C12 C13 C14 -0.19(18) . . . . ?
C12 C13 C14 C15 0.21(19) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C12 C11 C16 C15 -0.37(19) . . . . ?
C10 C11 C16 C15 175.69(12) . . . . ?
C22 N2 C17 O4 -5.8(2) . . . . ?
C18 N2 C17 O4 174.31(12) . . . . ?
C22 N2 C17 O3 173.55(10) . . . . ?
C18 N2 C17 O3 -6.34(13) . . . . ?
C2 O3 C17 O4 172.00(11) . . . . ?
C2 O3 C17 N2 -7.41(12) . . . . ?
C17 N2 C18 C19 -106.54(11) . . . . ?
C22 N2 C18 C19 73.57(14) . . . . ?
C17 N2 C18 C2 15.86(12) . . . . ?
C22 N2 C18 C2 -164.02(11) . . . . ?
O1 C2 C18 N2 -136.88(9) . . . . ?
O3 C2 C18 N2 -18.81(11) . . . . ?
N1 C2 C18 N2 101.76(10) . . . . ?
O1 C2 C18 C19 -13.33(14) . . . . ?
O3 C2 C18 C19 104.74(10) . . . . ?
N1 C2 C18 C19 -134.69(10) . . . . ?
N2 C18 C19 C20 50.87(14) . . . . ?
C2 C18 C19 C20 -63.79(13) . . . . ?
N2 C18 C19 C21 -74.90(13) . . . . ?
C2 C18 C19 C21 170.44(10) . . . . ?


_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.028
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx77_12
_database_code_depnum_ccdc_archive 'CCDC 1477537'
_audit_update_record             
;
2016-04-29 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 N2 O4'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   10.0012(12)
_cell_length_b                   10.3680(10)
_cell_length_c                   12.5874(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1305.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9737
_cell_measurement_theta_min      3.5077
_cell_measurement_theta_max      66.3220

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.868
_exptl_absorpt_correction_T_min  0.90240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13825
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.53
_diffrn_reflns_theta_max         66.40
_reflns_number_total             2291
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0332P)²+0.2707P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.16(15)
_refine_ls_number_reflns         2291
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0621
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration syn

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12114(8) 0.40696(8) 0.48270(7) 0.01830(19) Uani 1 1 d . . .
O2 O 0.34284(9) 0.42342(9) 0.51681(7) 0.0240(2) Uani 1 1 d . . .
O3 O -0.09699(8) 0.48153(8) 0.49884(7) 0.02002(19) Uani 1 1 d . . .
O4 O -0.18952(10) 0.31769(10) 0.26584(8) 0.0315(3) Uani 1 1 d . . .
N1 N 0.22065(10) 0.59344(10) 0.45120(9) 0.0186(2) Uani 1 1 d . . .
N2 N -0.01969(10) 0.44152(10) 0.33484(8) 0.0177(2) Uani 1 1 d . . .
C1 C 0.01750(12) 0.48921(12) 0.43794(10) 0.0165(3) Uani 1 1 d . . .
C2 C 0.07979(12) 0.62311(12) 0.44119(10) 0.0193(3) Uani 1 1 d . . .
H2A H 0.0611 0.6717 0.3751 0.023 Uiso 1 1 calc R . .
H2B H 0.0471 0.6732 0.5029 0.023 Uiso 1 1 calc R . .
C3 C 0.23998(12) 0.47268(11) 0.48657(10) 0.0174(3) Uani 1 1 d . . .
C4 C 0.32074(13) 0.69334(13) 0.46267(11) 0.0249(3) Uani 1 1 d . . .
H4A H 0.3139 0.7539 0.4031 0.037 Uiso 1 1 calc R . .
H4B H 0.4099 0.6542 0.4631 0.037 Uiso 1 1 calc R . .
H4C H 0.3062 0.7396 0.5296 0.037 Uiso 1 1 calc R . .
C5 C -0.18741(12) 0.38778(12) 0.45217(10) 0.0203(3) Uani 1 1 d . . .
H5 H -0.1783 0.3032 0.4897 0.024 Uiso 1 1 calc R . .
C6 C -0.13693(13) 0.37540(13) 0.33918(10) 0.0209(3) Uani 1 1 d . . .
C7 C -0.32951(13) 0.43509(15) 0.46052(11) 0.0286(3) Uani 1 1 d . . .
H7A H -0.3529 0.4471 0.5355 0.043 Uiso 1 1 calc R . .
H7B H -0.3899 0.3715 0.4286 0.043 Uiso 1 1 calc R . .
H7C H -0.3382 0.5174 0.4229 0.043 Uiso 1 1 calc R . .
C8 C 0.06474(12) 0.45122(13) 0.24046(10) 0.0210(3) Uani 1 1 d . . .
H8A H 0.0893 0.5428 0.2296 0.025 Uiso 1 1 calc R . .
H8B H 0.0124 0.4232 0.1778 0.025 Uiso 1 1 calc R . .
C9 C 0.19121(12) 0.37180(12) 0.24628(9) 0.0179(3) Uani 1 1 d . . .
C10 C 0.18662(14) 0.24127(13) 0.27114(10) 0.0223(3) Uani 1 1 d . . .
H10 H 0.1031 0.2009 0.2848 0.027 Uiso 1 1 calc R . .
C11 C 0.30330(15) 0.16990(14) 0.27609(11) 0.0281(3) Uani 1 1 d . . .
H11 H 0.2994 0.0807 0.2931 0.034 Uiso 1 1 calc R . .
C12 C 0.42578(15) 0.22747(15) 0.25647(11) 0.0304(3) Uani 1 1 d . . .
H12 H 0.5056 0.1781 0.2605 0.036 Uiso 1 1 calc R . .
C13 C 0.43138(14) 0.35698(15) 0.23103(11) 0.0283(3) Uani 1 1 d . . .
H13 H 0.5150 0.3968 0.2169 0.034 Uiso 1 1 calc R . .
C14 C 0.31401(13) 0.42881(13) 0.22619(10) 0.0216(3) Uani 1 1 d . . .
H14 H 0.3181 0.5179 0.2089 0.026 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3709(15) . ?
O1 C1 1.4558(14) . ?
O2 C3 1.2099(15) . ?
O3 C1 1.3802(15) . ?
O3 C5 1.4518(15) . ?
O4 C6 1.2194(17) . ?
N1 C3 1.3428(17) . ?
N1 C2 1.4475(16) . ?
N1 C4 1.4477(16) . ?
N2 C6 1.3594(17) . ?
N2 C1 1.4377(16) . ?
N2 C8 1.4609(16) . ?
C1 C2 1.5222(17) . ?
C5 C7 1.5072(18) . ?
C5 C6 1.5146(18) . ?
C8 C9 1.5110(17) . ?
C9 C14 1.3863(19) . ?
C9 C10 1.3898(19) . ?
C10 C11 1.383(2) . ?
C11 C12 1.385(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C1 109.87(9) . . ?
C1 O3 C5 109.31(9) . . ?
C3 N1 C2 111.54(10) . . ?
C3 N1 C4 122.31(11) . . ?
C2 N1 C4 121.98(10) . . ?
C6 N2 C1 111.12(10) . . ?
C6 N2 C8 124.47(11) . . ?
C1 N2 C8 124.11(10) . . ?
O3 C1 N2 105.48(9) . . ?
O3 C1 O1 109.99(10) . . ?
N2 C1 O1 109.40(9) . . ?
O3 C1 C2 112.16(10) . . ?
N2 C1 C2 116.35(10) . . ?
O1 C1 C2 103.45(9) . . ?
N1 C2 C1 101.93(10) . . ?
O2 C3 N1 128.33(11) . . ?
O2 C3 O1 122.58(11) . . ?
N1 C3 O1 109.08(10) . . ?
O3 C5 C7 109.95(10) . . ?
O3 C5 C6 103.24(10) . . ?
C7 C5 C6 114.04(11) . . ?
O4 C6 N2 126.09(12) . . ?
O4 C6 C5 127.50(12) . . ?
N2 C6 C5 106.41(10) . . ?
N2 C8 C9 114.01(10) . . ?
C14 C9 C10 119.04(12) . . ?
C14 C9 C8 120.03(11) . . ?
C10 C9 C8 120.93(12) . . ?
C11 C10 C9 120.22(13) . . ?
C10 C11 C12 120.50(13) . . ?
C13 C12 C11 119.74(13) . . ?
C12 C13 C14 119.75(14) . . ?
C9 C14 C13 120.74(12) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        66.40
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.034
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mx82_12
_database_code_depnum_ccdc_archive 'CCDC 1477538'
_audit_update_record             
;
2016-04-29 deposited with the CCDC.
2016-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N2 O4'
_chemical_formula_sum            'C20 H20 N2 O4'
_chemical_formula_weight         352.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   10.1661(6)
_cell_length_b                   8.2577(4)
_cell_length_c                   10.5397(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.382(6)
_cell_angle_gamma                90.00
_cell_volume                     864.21(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6101
_cell_measurement_theta_min      4.2908
_cell_measurement_theta_max      66.3865

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_min  0.70733
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9089
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         66.62
_reflns_number_total             2969
_reflns_number_gt                2886
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1285P)²+0.0488P] where P=(Fo²+2Fc²)/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       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_number_reflns         2969
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration syn

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.02188(16) 0.3240(2) 0.39555(15) 0.0236(4) Uani 1 1 d . . .
O2 O 1.14762(19) 0.1836(3) 0.56068(16) 0.0336(5) Uani 1 1 d . . .
O3 O 0.84501(16) 0.3544(2) 0.22018(16) 0.0240(4) Uani 1 1 d . . .
O4 O 1.01508(18) 0.6516(2) 0.07922(16) 0.0274(4) Uani 1 1 d . . .
N1 N 1.0893(2) 0.0792(3) 0.3530(2) 0.0268(5) Uani 1 1 d . . .
N2 N 1.05326(19) 0.4117(3) 0.19140(17) 0.0209(5) Uani 1 1 d . . .
C1 C 0.9776(2) 0.3041(3) 0.2566(2) 0.0211(5) Uani 1 1 d . . .
C2 C 0.9956(2) 0.1226(3) 0.2334(2) 0.0237(5) Uani 1 1 d . . .
H2 H 1.0395 0.1072 0.1579 0.028 Uiso 1 1 calc R . .
C3 C 1.0927(2) 0.1896(3) 0.4472(2) 0.0237(6) Uani 1 1 d . . .
C4 C 0.8656(3) 0.0260(4) 0.2123(3) 0.0356(7) Uani 1 1 d . . .
H4A H 0.8255 0.0370 0.2885 0.053 Uiso 1 1 calc R . .
H4B H 0.8848 -0.0884 0.1994 0.053 Uiso 1 1 calc R . .
H4C H 0.8026 0.0671 0.1353 0.053 Uiso 1 1 calc R . .
C5 C 1.1419(3) -0.0832(4) 0.3792(3) 0.0349(7) Uani 1 1 d . . .
H5A H 1.1894 -0.1155 0.3115 0.052 Uiso 1 1 calc R . .
H5B H 1.0675 -0.1584 0.3798 0.052 Uiso 1 1 calc R . .
H5C H 1.2046 -0.0855 0.4640 0.052 Uiso 1 1 calc R . .
C6 C 0.8384(2) 0.5152(3) 0.1644(2) 0.0214(5) Uani 1 1 d . . .
H6 H 0.8217 0.5969 0.2291 0.026 Uiso 1 1 calc R . .
C7 C 0.9779(2) 0.5394(3) 0.1376(2) 0.0212(5) Uani 1 1 d . . .
C8 C 0.7257(2) 0.5196(3) 0.0454(2) 0.0194(5) Uani 1 1 d . . .
C9 C 0.7255(2) 0.4132(3) -0.0572(2) 0.0234(5) Uani 1 1 d . . .
H9 H 0.7989 0.3411 -0.0541 0.028 Uiso 1 1 calc R . .
C10 C 0.6187(2) 0.4121(4) -0.1635(2) 0.0292(6) Uani 1 1 d . . .
H10 H 0.6186 0.3388 -0.2331 0.035 Uiso 1 1 calc R . .
C11 C 0.5117(3) 0.5181(4) -0.1687(2) 0.0346(7) Uani 1 1 d . . .
H11 H 0.4382 0.5174 -0.2416 0.042 Uiso 1 1 calc R . .
C12 C 0.5122(3) 0.6243(4) -0.0676(3) 0.0335(7) Uani 1 1 d . . .
H12 H 0.4388 0.6966 -0.0713 0.040 Uiso 1 1 calc R . .
C13 C 0.6192(3) 0.6265(3) 0.0395(3) 0.0270(6) Uani 1 1 d . . .
H13 H 0.6194 0.7008 0.1083 0.032 Uiso 1 1 calc R . .
C14 C 1.1928(2) 0.3890(3) 0.1825(2) 0.0239(5) Uani 1 1 d . . .
H14A H 1.2029 0.4279 0.0963 0.029 Uiso 1 1 calc R . .
H14B H 1.2123 0.2714 0.1866 0.029 Uiso 1 1 calc R . .
C15 C 1.2981(2) 0.4729(3) 0.2857(2) 0.0213(5) Uani 1 1 d . . .
C16 C 1.4304(2) 0.4703(3) 0.2695(3) 0.0274(6) Uani 1 1 d . . .
H16 H 1.4510 0.4172 0.1961 0.033 Uiso 1 1 calc R . .
C17 C 1.5322(3) 0.5440(4) 0.3588(3) 0.0336(7) Uani 1 1 d . . .
H17 H 1.6221 0.5409 0.3467 0.040 Uiso 1 1 calc R . .
C18 C 1.5036(3) 0.6227(4) 0.4667(3) 0.0317(6) Uani 1 1 d . . .
H18 H 1.5733 0.6738 0.5280 0.038 Uiso 1 1 calc R . .
C19 C 1.3724(3) 0.6253(3) 0.4833(2) 0.0286(6) Uani 1 1 d . . .
H19 H 1.3519 0.6788 0.5565 0.034 Uiso 1 1 calc R . .
C20 C 1.2697(2) 0.5500(3) 0.3935(2) 0.0243(5) Uani 1 1 d . . .
H20 H 1.1800 0.5516 0.4064 0.029 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.370(3) . ?
O1 C1 1.446(3) . ?
O2 C3 1.208(3) . ?
O3 C1 1.383(3) . ?
O3 C6 1.448(3) . ?
O4 C7 1.216(3) . ?
N1 C3 1.343(4) . ?
N1 C5 1.448(4) . ?
N1 C2 1.452(3) . ?
N2 C7 1.355(4) . ?
N2 C1 1.443(3) . ?
N2 C14 1.453(3) . ?
C1 C2 1.536(4) . ?
C2 C4 1.519(4) . ?
C6 C8 1.507(3) . ?
C6 C7 1.517(3) . ?
C8 C13 1.388(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.383(3) . ?
C10 C11 1.388(4) . ?
C11 C12 1.379(5) . ?
C12 C13 1.390(4) . ?
C14 C15 1.519(3) . ?
C15 C20 1.386(4) . ?
C15 C16 1.392(3) . ?
C16 C17 1.382(4) . ?
C17 C18 1.393(4) . ?
C18 C19 1.382(4) . ?
C19 C20 1.396(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C1 109.44(19) . . ?
C1 O3 C6 110.21(18) . . ?
C3 N1 C5 122.6(2) . . ?
C3 N1 C2 112.5(2) . . ?
C5 N1 C2 122.7(2) . . ?
C7 N2 C1 111.57(19) . . ?
C7 N2 C14 123.05(19) . . ?
C1 N2 C14 125.4(2) . . ?
O3 C1 N2 105.67(19) . . ?
O3 C1 O1 108.68(18) . . ?
N2 C1 O1 109.27(19) . . ?
O3 C1 C2 113.0(2) . . ?
N2 C1 C2 115.5(2) . . ?
O1 C1 C2 104.51(18) . . ?
N1 C2 C4 112.7(2) . . ?
N1 C2 C1 100.42(19) . . ?
C4 C2 C1 113.9(2) . . ?
O2 C3 N1 129.6(2) . . ?
O2 C3 O1 121.3(2) . . ?
N1 C3 O1 109.17(19) . . ?
O3 C6 C8 108.71(19) . . ?
O3 C6 C7 103.46(19) . . ?
C8 C6 C7 114.63(18) . . ?
O4 C7 N2 126.6(2) . . ?
O4 C7 C6 126.8(2) . . ?
N2 C7 C6 106.7(2) . . ?
C13 C8 C9 119.6(2) . . ?
C13 C8 C6 120.0(2) . . ?
C9 C8 C6 120.3(2) . . ?
C10 C9 C8 120.2(2) . . ?
C9 C10 C11 120.0(2) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C13 120.6(3) . . ?
C8 C13 C12 119.7(3) . . ?
N2 C14 C15 116.3(2) . . ?
C20 C15 C16 118.9(2) . . ?
C20 C15 C14 123.9(2) . . ?
C16 C15 C14 117.2(2) . . ?
C17 C16 C15 120.8(3) . . ?
C16 C17 C18 120.3(2) . . ?
C19 C18 C17 119.2(2) . . ?
C18 C19 C20 120.6(2) . . ?
C15 C20 C19 120.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        66.62
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.060
