data_06ac100
_publcif_datablock.id '{c7b5b1f8-24a0-4ea7-81ce-9dd7fee9b3b6}'

_audit_update_record
;
2015-04-16 # Formatted by IUCr publCIF system
;

_audit_creation_method            SHELXL-2013

loop_
  _publ_author_name
 'Mark Light'
 'Alun Coker'

_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C16 H24 N2 O6, H2 O'
_chemical_formula_sum
 'C16 H26 N2 O7' 
_chemical_formula_weight          358.39

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'

_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'

_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+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'

_cell_length_a                    10.1602(2)
_cell_length_b                    10.4228(2)
_cell_length_c                    16.3042(3)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1726.58(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2267
_cell_measurement_theta_max       27.48
_cell_measurement_theta_min       2.91

_exptl_crystal_description        Block 
_exptl_crystal_colour             Colourless
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.379          
_exptl_crystal_F_000              768
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.220
_exptl_crystal_size_mid           0.100
_exptl_crystal_size_min           0.080
_exptl_absorpt_coefficient_mu     0.108
_shelx_estimated_absorpt_T_min    0.977
_shelx_estimated_absorpt_T_max    0.991
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_max   0.9914
_exptl_absorpt_correction_T_min   0.9666
_exptl_absorpt_process_details    
;
SADABS V2.10 (Sheldrick, G.M., 2003)
; 

_exptl_special_details
;
SADABS was used to perform the Absorption correction Parameter refinement
on 16028 reflections reduced R(int) from 0.0917 to 0.0391 Ratio of
minimum to maximum apparent transmission: 0.883992 The given Tmin and Tmax
were generated using the SHELX SIZE command
;

_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Bruker Nonius FR591 Rotating Anode'                       
_diffrn_measurement_device_type   'Bruker-Nonius CCD camera on κ-goniostat' 
_diffrn_measurement_method        'φ & ω scans to fill the asymmetric unit' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_reflns_number             15611
_diffrn_reflns_av_unetI/netI      0.0336
_diffrn_reflns_av_R_equivalents   0.0357
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.066
_diffrn_reflns_theta_max          27.479
_diffrn_reflns_theta_full         27.500
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.995
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.995
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.993
_reflns_number_total              3932
_reflns_number_gt                 3642
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.748
_reflns_Friedel_fraction_max      0.991
_reflns_Friedel_fraction_full     0.989

_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        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     'CAMERON (Watkin, et al., 1993)'
_computing_publication_material   'WINGX (Farrugia, 1998)'

_refine_special_details
;
With the exception of those on the water molecule (freely refined) all hydrogen
atoms were placed in idealized positions and refined using a riding model. The
proline ring containing N1 was modelled as disordered between two possible
conformations, thermal parameter constraints were applied to equivalent atoms
across the two parts, occupancy values were initially refined but then fixed
in the final refinement cycles.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0298P)²+0.6051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_chemical_absolute_configuration  unk
_refine_ls_number_reflns          3932
_refine_ls_number_parameters      235
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0420
_refine_ls_R_factor_gt            0.0370
_refine_ls_wR_factor_ref          0.0857
_refine_ls_wR_factor_gt           0.0823
_refine_ls_goodness_of_fit_ref    1.089
_refine_ls_restrained_S_all       1.089
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000

loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_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 -0.27599(16) 0.49429(15) 0.10184(10) 0.0247(4) Uani 1 1 d . . . . .
H1 H -0.3540 0.4919 0.1188 0.037 Uiso 1 1 d R U . . .
O2 O -0.26751(16) 0.67193(16) 0.17830(10) 0.0243(4) Uani 1 1 d . . . . .
O4 O 0.03675(16) 0.55220(16) 0.23247(10) 0.0233(4) Uani 1 1 d . . . . .
O5 O 0.52118(15) 0.95405(15) 0.37603(10) 0.0220(4) Uani 1 1 d . . . . .
O7 O 0.80935(19) 1.00031(18) 0.53630(11) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.7890 1.0140 0.5855 0.053 Uiso 1 1 d R U . . .
O8 O 0.66137(16) 0.84334(17) 0.54865(10) 0.0268(4) Uani 1 1 d . . . . .
N1A N 0.00161(18) 0.70215(18) 0.13622(11) 0.0181(4) Uani 0.8 1 d . . P A 1
N2 N 0.66660(18) 0.79291(17) 0.38293(11) 0.0165(4) Uani 1 1 d . . . . .
C1 C -0.2181(2) 0.5975(2) 0.12997(13) 0.0170(4) Uani 1 1 d . . . . .
C2A C -0.0844(2) 0.6156(2) 0.09026(14) 0.0193(5) Uani 0.8 1 d . . P A 1
H2A H -0.0405 0.5310 0.0809 0.023 Uiso 0.8 1 calc R U P A 1
C3A C -0.1056(6) 0.6884(5) 0.0069(5) 0.0239(11) Uani 0.8 1 d . . P A 1
H3A1 H -0.1065 0.6273 -0.0396 0.029 Uiso 0.8 1 calc R U P A 1
H3A2 H -0.1897 0.7363 0.0074 0.029 Uiso 0.8 1 calc R U P A 1
C4A C 0.0101(3) 0.7794(3) -0.00001(18) 0.0216(6) Uani 0.8 1 d . . P A 1
H4A1 H -0.0112 0.8536 -0.0356 0.026 Uiso 0.8 1 calc R U P A 1
H4A2 H 0.0889 0.7353 -0.0219 0.026 Uiso 0.8 1 calc R U P A 1
C5A C 0.0317(10) 0.8228(10) 0.0918(5) 0.0186(11) Uani 0.8 1 d . . P A 1
H5A1 H 0.1234 0.8510 0.1016 0.022 Uiso 0.8 1 calc R U P A 1
H5A2 H -0.0294 0.8926 0.1075 0.022 Uiso 0.8 1 calc R U P A 1
C6 C 0.0617(2) 0.6601(2) 0.20453(13) 0.0174(4) Uani 1 1 d . . . . .
C7 C 0.1651(2) 0.7448(2) 0.24297(14) 0.0184(5) Uani 1 1 d . . . . .
H7A H 0.1695 0.7285 0.3027 0.022 Uiso 1 1 calc R U . . .
H7B H 0.1421 0.8362 0.2344 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2993(2) 0.7158(2) 0.20340(13) 0.0190(5) Uani 1 1 d . . . . .
H8A H 0.3193 0.6235 0.2106 0.023 Uiso 1 1 calc R U . . .
H8B H 0.2935 0.7330 0.1438 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4122(2) 0.7947(2) 0.23932(14) 0.0210(5) Uani 1 1 d . . . . .
H9A H 0.3865 0.8863 0.2408 0.025 Uiso 1 1 calc R U . . .
H9B H 0.4904 0.7865 0.2035 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4474(2) 0.7501(2) 0.32620(14) 0.0209(5) Uani 1 1 d . . . . .
H10A H 0.3671 0.7493 0.3606 0.025 Uiso 1 1 calc R U . . .
H10B H 0.4827 0.6616 0.3241 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5484(2) 0.8382(2) 0.36387(13) 0.0174(4) Uani 1 1 d . . . . .
C12 C 0.7109(2) 0.6579(2) 0.37863(14) 0.0214(5) Uani 1 1 d . . . . .
H12A H 0.7137 0.6276 0.3211 0.026 Uiso 1 1 calc R U . . .
H12B H 0.6517 0.6013 0.4105 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8486(2) 0.6604(2) 0.41604(16) 0.0246(5) Uani 1 1 d . . . . .
H13A H 0.8459 0.6353 0.4746 0.029 Uiso 1 1 calc R U . . .
H13B H 0.9082 0.6013 0.3864 0.029 Uiso 1 1 calc R U . . .
C14 C 0.8941(2) 0.7992(2) 0.40671(15) 0.0221(5) Uani 1 1 d . . . . .
H14A H 0.9329 0.8141 0.3518 0.027 Uiso 1 1 calc R U . . .
H14B H 0.9599 0.8216 0.4491 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7671(2) 0.8772(2) 0.41791(13) 0.0167(4) Uani 1 1 d . . . . .
H15 H 0.7721 0.9593 0.3863 0.020 Uiso 1 1 calc R U . . .
C16 C 0.7380(2) 0.9039(2) 0.50747(14) 0.0190(4) Uani 1 1 d . . . . .
N1B N 0.00161(18) 0.70215(18) 0.13622(11) 0.0181(4) Uani 0.2 1 d . . P A 2
C2B C -0.0844(2) 0.6156(2) 0.09026(14) 0.0193(5) Uani 0.2 1 d . . P A 2
H2B H -0.0407 0.5297 0.0900 0.023 Uiso 0.2 1 calc R U P A 2
C3B C -0.088(3) 0.659(3) 0.007(2) 0.0239(11) Uani 0.2 1 d . . P A 2
H3B1 H -0.1720 0.6378 -0.0204 0.029 Uiso 0.2 1 calc R U P A 2
H3B2 H -0.0138 0.6236 -0.0258 0.029 Uiso 0.2 1 calc R U P A 2
C4B C -0.0729(12) 0.8021(11) 0.0195(7) 0.0216(6) Uani 0.2 1 d . . P A 2
H4B1 H -0.0454 0.8452 -0.0318 0.026 Uiso 0.2 1 calc R U P A 2
H4B2 H -0.1565 0.8405 0.0386 0.026 Uiso 0.2 1 calc R U P A 2
C5B C 0.024(4) 0.812(5) 0.079(2) 0.0186(11) Uani 0.2 1 d . . P A 2
H5B1 H 0.0165 0.8945 0.1086 0.022 Uiso 0.2 1 calc R U P A 2
H5B2 H 0.1125 0.8063 0.0540 0.022 Uiso 0.2 1 calc R U P A 2
O9 O 0.25090(17) 0.43875(16) 0.31308(10) 0.0254(4) Uani 1 1 d . . . B .
H97 H 0.2440 0.3580 0.3120 0.038 Uiso 1 1 d R U . B .
H98 H 0.1820 0.4710 0.2890 0.038 Uiso 1 1 d R U . B .


_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 C1 1.309(3) . ?
O2 C1 1.214(3) . ?
O4 C6 1.240(3) . ?
O5 C11 1.255(3) . ?
O7 C16 1.325(3) . ?
O8 C16 1.206(3) . ?
N1A C6 1.343(3) . ?
N1A C2A 1.462(3) . ?
N1A C5A 1.483(12) . ?
N2 C11 1.327(3) . ?
N2 C15 1.463(3) . ?
N2 C12 1.479(3) . ?
C1 C2A 1.516(3) . ?
C2A C3A 1.572(7) . ?
C3A C4A 1.515(7) . ?
C4A C5A 1.580(7) . ?
C6 C7 1.509(3) . ?
C7 C8 1.538(3) . ?
C8 C9 1.527(3) . ?
C9 C10 1.533(3) . ?
C10 C11 1.508(3) . ?
C12 C13 1.527(3) . ?
C13 C14 1.526(3) . ?
C14 C15 1.537(3) . ?
C15 C16 1.515(3) . ?
C3B C4B 1.51(3) . ?
C4B C5B 1.39(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
C6 N1A C2A 119.70(19) . . ?
C6 N1A C5A 126.0(3) . . ?
C2A N1A C5A 113.3(3) . . ?
C11 N2 C15 120.62(18) . . ?
C11 N2 C12 127.03(19) . . ?
C15 N2 C12 112.20(17) . . ?
O2 C1 O1 124.5(2) . . ?
O2 C1 C2A 124.6(2) . . ?
O1 C1 C2A 110.82(19) . . ?
N1A C2A C1 113.17(19) . . ?
N1A C2A C3A 103.2(3) . . ?
C1 C2A C3A 107.9(3) . . ?
C4A C3A C2A 105.1(4) . . ?
C3A C4A C5A 102.5(5) . . ?
N1A C5A C4A 101.0(5) . . ?
O4 C6 N1A 120.5(2) . . ?
O4 C6 C7 121.4(2) . . ?
N1A C6 C7 118.0(2) . . ?
C6 C7 C8 109.16(17) . . ?
C9 C8 C7 113.49(18) . . ?
C8 C9 C10 111.48(19) . . ?
C11 C10 C9 110.53(18) . . ?
O5 C11 N2 120.3(2) . . ?
O5 C11 C10 120.02(19) . . ?
N2 C11 C10 119.7(2) . . ?
N2 C12 C13 104.10(18) . . ?
C14 C13 C12 104.72(19) . . ?
C13 C14 C15 103.61(18) . . ?
N2 C15 C16 110.47(17) . . ?
N2 C15 C14 102.82(17) . . ?
C16 C15 C14 112.03(18) . . ?
O8 C16 O7 123.5(2) . . ?
O8 C16 C15 124.5(2) . . ?
O7 C16 C15 111.97(18) . . ?
C5B C4B C3B 104(3) . . ?

loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1 O5  0.84 1.75 2.552(2) 160.2 4_545
O7 H7 O9  0.84 1.77 2.605(2) 173.5 3_566
C4A H4A1 O5  0.99 2.47 3.450(3) 169.6 2_574
C7 H7A O8  0.99 2.54 3.520(3) 171.5 3_466
C12 H12A O2  0.99 2.38 3.277(3) 150.1 1_655
C13 H13A O1  0.99 2.58 3.510(3) 157.4 2_565
O9 H97 O2  0.84 1.96 2.790(2) 166.9 4_545
O9 H98 O4  0.87 1.93 2.804(2) 176.0 .

_refine_diff_density_max    0.212
_refine_diff_density_min   -0.235
_refine_diff_density_rms    0.048

_shelxl_version_number 2013-3



loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
'{c7b5b1f8-24a0-4ea7-81ce-9dd7fee9b3b6}' y y y

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
