#=============================================================================
 
data_is_ea7131001

_audit_author_name                'Villinger, A.' 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'

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

# CHEMICAL DATA

_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C18 H18 N2 O2, 3(H2 O)'
_chemical_formula_sum
 'C18 H18 N2 O5' 
_chemical_formula_weight          342.34

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

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

# CRYSTAL DATA
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            33
_space_group_name_H-M_alt         'P n a 21'
_space_group_name_Hall            'P 2c -2n'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    7.7883(4)
_cell_length_b                    11.6157(6)
_cell_length_c                    18.1845(10)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1645.09(15)
_cell_formula_units_Z             4
_cell_measurement_temperature     123(2)
_cell_measurement_reflns_used      9885
_cell_measurement_theta_min        3.15
_cell_measurement_theta_max       32.25

_exptl_crystal_description       'block'
_exptl_crystal_colour            'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.382          
_exptl_crystal_F_000              720
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.350
_exptl_crystal_size_mid           0.090
_exptl_crystal_size_min           0.060
_exptl_absorpt_coefficient_mu     0.102
_shelx_estimated_absorpt_T_min    0.965
_shelx_estimated_absorpt_T_max    0.994
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7146 
_exptl_absorpt_correction_T_max    0.7464 
_exptl_absorpt_process_details    '(SADABS; Sheldrick, 2014)'

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

# EXPERIMENTAL DATA
 
 
_diffrn_ambient_temperature       123(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_measurement_device_type   'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method        'phi and omega scans'  
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             58987
_diffrn_reflns_av_unetI/netI      0.0386
_diffrn_reflns_av_R_equivalents   0.0633
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          3.149
_diffrn_reflns_theta_max          32.496
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              5942
_reflns_number_gt                 5047
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.947
_reflns_Friedel_fraction_max      0.998
_reflns_Friedel_fraction_full     0.997
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker Apex V7.51A'
_computing_cell_refinement        'Bruker Apex V7.51A'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'Bruker SHELXTL'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'ORTEP-3v2.01 (Farrugia, 1997)' 
_computing_publication_material   'SHELXL-2014/7 (Sheldrick, 2014)'

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

# REFINEMENT DATA 
 
_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 > 2σ(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

 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0548P)²+0.2564P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    0.2(9)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          5942
_refine_ls_number_parameters      251
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0606
_refine_ls_R_factor_gt            0.0447
_refine_ls_wR_factor_ref          0.1014
_refine_ls_wR_factor_gt           0.0948
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.27747(17) 0.12659(12) 0.60313(8) 0.0157(3) Uani 1 1 d . . . . .
O2 O 0.60268(19) 0.90234(12) 0.50234(9) 0.0201(3) Uani 1 1 d . . . . .
N1 N 0.49249(19) 0.36504(13) 0.46419(8) 0.0102(3) Uani 1 1 d . . . . .
N2 N 0.5692(2) 0.56382(13) 0.44480(8) 0.0126(3) Uani 1 1 d . . . . .
C1 C 0.3883(2) 0.39857(15) 0.52185(10) 0.0118(3) Uani 1 1 d . . . . .
H1 H 0.3675 0.4783 0.5292 0.014 Uiso 1 1 calc R U . . .
C2 C 0.3150(2) 0.32197(15) 0.56817(10) 0.0124(3) Uani 1 1 d . . . . .
H2 H 0.2447 0.3490 0.6072 0.015 Uiso 1 1 calc R U . . .
C3 C 0.3415(2) 0.20044(15) 0.55933(10) 0.0113(3) Uani 1 1 d . . . . .
C4 C 0.4395(2) 0.16863(15) 0.49669(10) 0.0108(3) Uani 1 1 d . . . . .
H4 H 0.4557 0.0891 0.4868 0.013 Uiso 1 1 calc R U . . .
C5 C 0.5123(2) 0.24791(15) 0.44948(9) 0.0099(3) Uani 1 1 d . . . . .
C6 C 0.6047(2) 0.21496(15) 0.38275(10) 0.0105(3) Uani 1 1 d . . . . .
C7 C 0.6227(2) 0.09800(15) 0.36279(11) 0.0141(3) Uani 1 1 d . . . . .
H7 H 0.5789 0.0393 0.3940 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7042(3) 0.06900(17) 0.29770(11) 0.0169(4) Uani 1 1 d . . . . .
H8 H 0.7143 -0.0097 0.2841 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7719(3) 0.15449(18) 0.25164(11) 0.0183(4) Uani 1 1 d . . . . .
H9 H 0.8276 0.1335 0.2071 0.022 Uiso 1 1 calc R U . . .
C10 C 0.7580(2) 0.26903(17) 0.27082(10) 0.0161(4) Uani 1 1 d . . . . .
H10 H 0.8054 0.3268 0.2399 0.019 Uiso 1 1 calc R U . . .
C11 C 0.6734(2) 0.30019(15) 0.33632(10) 0.0118(3) Uani 1 1 d . . . . .
C12 C 0.6621(2) 0.41866(15) 0.35885(10) 0.0133(3) Uani 1 1 d . . . . .
H12 H 0.7155 0.4768 0.3301 0.016 Uiso 1 1 calc R U . . .
C13 C 0.5771(2) 0.44754(15) 0.42005(10) 0.0113(3) Uani 1 1 d . . . . .
C14 C 0.5046(2) 0.64752(15) 0.39905(10) 0.0142(4) Uani 1 1 d . . . . .
H14 H 0.4532 0.6257 0.3538 0.017 Uiso 1 1 calc R U . . .
C15 C 0.5127(3) 0.76043(16) 0.41716(11) 0.0160(4) Uani 1 1 d . . . . .
H15 H 0.4654 0.8159 0.3846 0.019 Uiso 1 1 calc R U . . .
C16 C 0.5909(2) 0.79835(15) 0.48453(11) 0.0143(4) Uani 1 1 d . . . . .
C17 C 0.6566(3) 0.70667(16) 0.53080(11) 0.0149(4) Uani 1 1 d . . . . .
H17 H 0.7080 0.7254 0.5766 0.018 Uiso 1 1 calc R U . . .
C18 C 0.6462(2) 0.59518(15) 0.51011(10) 0.0134(3) Uani 1 1 d . . . . .
H18 H 0.6929 0.5373 0.5411 0.016 Uiso 1 1 calc R U . . .
O3 O 0.5743(2) 0.33354(14) 0.72638(8) 0.0205(3) Uani 1 1 d . . . . .
H3A H 0.463(6) 0.350(3) 0.718(2) 0.056(11) Uiso 1 1 d . . . . .
H3B H 0.623(5) 0.352(4) 0.687(3) 0.068(12) Uiso 1 1 d . . . . .
O4 O 0.7867(2) 0.61634(15) 0.24851(9) 0.0229(3) Uani 1 1 d . . . . .
H4A H 0.834(4) 0.572(3) 0.2216(19) 0.033(8) Uiso 1 1 d . . . . .
H4B H 0.847(4) 0.683(3) 0.2457(19) 0.041(9) Uiso 1 1 d . . . . .
O5 O 0.5410(2) 0.97418(14) 0.64629(9) 0.0236(3) Uani 1 1 d . . . . .
H5A H 0.573(4) 0.946(3) 0.602(2) 0.041(9) Uiso 1 1 d . . . . .
H5B H 0.447(4) 1.016(3) 0.635(2) 0.038(8) Uiso 1 1 d . . . . .
 

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

# MOLECULAR GEOMETRY
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C3 1.272(2) . ?
O2 C16 1.254(2) . ?
N1 C1 1.382(2) . ?
N1 C5 1.395(2) . ?
N1 C13 1.413(2) . ?
N2 C14 1.375(2) . ?
N2 C18 1.380(2) . ?
N2 C13 1.425(2) . ?
C1 C2 1.352(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.436(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(2) . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.462(2) . ?
C6 C11 1.407(2) . ?
C6 C7 1.413(2) . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.402(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.409(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.439(2) . ?
C12 C13 1.338(3) . ?
C12 H12 0.9500 . ?
C14 C15 1.354(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.438(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.450(3) . ?
C17 C18 1.351(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O3 H3A 0.90(4) . ?
O3 H3B 0.84(5) . ?
O4 H4A 0.80(4) . ?
O4 H4B 0.91(4) . ?
O5 H5A 0.90(4) . ?
O5 H5B 0.91(3) . ?
 
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
C1 N1 C5 119.03(15) . . ?
C1 N1 C13 120.91(15) . . ?
C5 N1 C13 120.05(15) . . ?
C14 N2 C18 119.56(15) . . ?
C14 N2 C13 119.67(15) . . ?
C18 N2 C13 120.22(15) . . ?
C2 C1 N1 122.37(16) . . ?
C2 C1 H1 118.8 . . ?
N1 C1 H1 118.8 . . ?
C1 C2 C3 121.11(16) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
O1 C3 C4 122.50(16) . . ?
O1 C3 C2 122.44(16) . . ?
C4 C3 C2 115.02(15) . . ?
C5 C4 C3 123.09(16) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 N1 119.05(16) . . ?
C4 C5 C6 122.94(16) . . ?
N1 C5 C6 117.97(15) . . ?
C11 C6 C7 118.98(16) . . ?
C11 C6 C5 120.08(15) . . ?
C7 C6 C5 120.92(16) . . ?
C8 C7 C6 119.92(18) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.72(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.15(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.89(18) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C6 C11 C10 120.31(16) . . ?
C6 C11 C12 118.63(16) . . ?
C10 C11 C12 121.00(17) . . ?
C13 C12 C11 120.45(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 N1 122.24(16) . . ?
C12 C13 N2 121.45(16) . . ?
N1 C13 N2 116.31(15) . . ?
C15 C14 N2 121.39(18) . . ?
C15 C14 H14 119.3 . . ?
N2 C14 H14 119.3 . . ?
C14 C15 C16 121.59(17) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
O2 C16 C15 123.11(17) . . ?
O2 C16 C17 122.12(18) . . ?
C15 C16 C17 114.77(16) . . ?
C18 C17 C16 121.41(18) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 N2 121.26(17) . . ?
C17 C18 H18 119.4 . . ?
N2 C18 H18 119.4 . . ?
H3A O3 H3B 103(3) . . ?
H4A O4 H4B 106(3) . . ?
H5A O5 H5B 103(3) . . ?
 
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
C5 N1 C1 C2 5.2(3) . . . . ?
C13 N1 C1 C2 -175.39(16) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
C1 C2 C3 O1 178.27(17) . . . . ?
C1 C2 C3 C4 -3.8(2) . . . . ?
O1 C3 C4 C5 -178.76(17) . . . . ?
C2 C3 C4 C5 3.3(2) . . . . ?
C3 C4 C5 N1 1.3(3) . . . . ?
C3 C4 C5 C6 -176.36(16) . . . . ?
C1 N1 C5 C4 -5.5(2) . . . . ?
C13 N1 C5 C4 175.00(16) . . . . ?
C1 N1 C5 C6 172.22(15) . . . . ?
C13 N1 C5 C6 -7.2(2) . . . . ?
C4 C5 C6 C11 178.91(17) . . . . ?
N1 C5 C6 C11 1.2(2) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
N1 C5 C6 C7 -177.12(16) . . . . ?
C11 C6 C7 C8 -1.2(3) . . . . ?
C5 C6 C7 C8 177.19(17) . . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C7 C6 C11 C10 0.3(3) . . . . ?
C5 C6 C11 C10 -178.09(16) . . . . ?
C7 C6 C11 C12 -176.91(16) . . . . ?
C5 C6 C11 C12 4.7(2) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C9 C10 C11 C12 177.88(17) . . . . ?
C6 C11 C12 C13 -4.8(3) . . . . ?
C10 C11 C12 C13 178.03(18) . . . . ?
C11 C12 C13 N1 -1.3(3) . . . . ?
C11 C12 C13 N2 177.83(16) . . . . ?
C1 N1 C13 C12 -171.96(17) . . . . ?
C5 N1 C13 C12 7.5(3) . . . . ?
C1 N1 C13 N2 8.9(2) . . . . ?
C5 N1 C13 N2 -171.65(15) . . . . ?
C14 N2 C13 C12 57.1(3) . . . . ?
C18 N2 C13 C12 -114.39(19) . . . . ?
C14 N2 C13 N1 -123.78(17) . . . . ?
C18 N2 C13 N1 64.8(2) . . . . ?
C18 N2 C14 C15 -0.9(3) . . . . ?
C13 N2 C14 C15 -172.46(18) . . . . ?
N2 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 O2 178.92(19) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
O2 C16 C17 C18 -178.57(19) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 N2 -1.5(3) . . . . ?
C14 N2 C18 C17 1.3(3) . . . . ?
C13 N2 C18 C17 172.76(18) . . . . ?
 
_refine_diff_density_max    0.334
_refine_diff_density_min   -0.254
_refine_diff_density_rms    0.055



