# 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_rjg150005_fa
_database_code_depnum_ccdc_archive 'CCDC 1471854'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-05-26 downloaded from the CCDC.
;
_audit_creation_date             2016-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'Diammonium (2R,6S)-tetrahydro-2H-pyran-2,6-dicarboxylate.(2R,6S)-tetrahydro-2H-pyran-2,6-dicarboxylic acid'
_chemical_formula_moiety         '0.5(C7 H9.36 O5), 0.5(C7 H8.64 O5), H4 N'
_chemical_formula_sum            'C7 H13 N O5'
_chemical_formula_weight         191.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H16 N2 O5'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9141(2)
_cell_length_b                   9.3897(3)
_cell_length_c                   14.4781(5)
_cell_angle_alpha                101.468(3)
_cell_angle_beta                 96.993(3)
_cell_angle_gamma                98.349(3)
_cell_volume                     900.34(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7648
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.7850
_cell_measurement_theta_min      3.1400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12629
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.873
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   13.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   57.0000 -120.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -77.0000   90.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -57.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega   96.00  122.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  123.8262 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   75.00  132.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -156.0984 57

#__ type_ start__ end____ width___ exp.time_
  6 omega  116.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00   51.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -156.0984 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   97.00  123.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  127.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   62.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   18.00   43.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00   93.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   34.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega   62.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 17 omega   52.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 63

#__ type_ start__ end____ width___ exp.time_
 19 omega   25.00   52.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   23.00   49.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   35.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 22 omega   64.00  133.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
 23 omega   20.00   46.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   22.00   58.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 26 omega   78.00  121.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 27 omega   83.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000   75.5260 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   22.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 44

#__ type_ start__ end____ width___ exp.time_
 29 omega   10.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  123.8262 67

#__ type_ start__ end____ width___ exp.time_
 30 omega   81.00  120.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -48.8970 39

#__ type_ start__ end____ width___ exp.time_
 31 omega -120.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
 32 omega -116.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
 33 omega -120.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 34 omega  -34.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -38.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 35 omega  -34.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -38.0000 -150.0000 102

#__ type_ start__ end____ width___ exp.time_
 36 omega   63.00  168.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -150.0000 105

#__ type_ start__ end____ width___ exp.time_
 37 omega   63.00  171.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  150.0000 108

#__ type_ start__ end____ width___ exp.time_
 38 omega   60.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 112

#__ type_ start__ end____ width___ exp.time_
 39 omega   60.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 112
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2011152000
_diffrn_orient_matrix_UB_12      0.0520423000
_diffrn_orient_matrix_UB_13      -0.0114890000
_diffrn_orient_matrix_UB_21      0.1071215000
_diffrn_orient_matrix_UB_22      0.1614471000
_diffrn_orient_matrix_UB_23      0.0216614000
_diffrn_orient_matrix_UB_31      0.0068984000
_diffrn_orient_matrix_UB_32      -0.0113880000
_diffrn_orient_matrix_UB_33      -0.1071383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2906
_reflns_number_total             3184
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0422P)²+0.3475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H,H) groups
2. Restrained distances
 O10-H10 \\sim O2-H2
 with sigma of 0.02
 O8-H8 \\sim O5-H5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H10)
Uiso(H5) = Uiso(H8)
4. Others
 Sof(H10)=1-FVAR(1)
 Sof(H2)=FVAR(1)
 Sof(H8)=1-FVAR(2)
 Sof(H5)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5A), C8(H8A), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.00049(13) 0.29250(10) -0.00713(6) 0.0197(2) Uani 1 1 d . . . . .
O2 O 0.03161(13) 0.20150(11) 0.15093(7) 0.0218(2) Uani 1 1 d D . . . .
O3 O -0.29036(13) 0.19312(11) 0.16134(7) 0.0253(2) Uani 1 1 d . . . . .
O4 O 0.32286(14) 0.40370(12) -0.07182(7) 0.0304(2) Uani 1 1 d . . . . .
O5 O 0.14992(15) 0.46105(11) -0.19330(7) 0.0258(2) Uani 1 1 d D . . . .
O6 O 0.50758(12) 0.30857(10) 0.50570(6) 0.0198(2) Uani 1 1 d . . . . .
O7 O 0.88077(14) 0.40183(12) 0.58764(7) 0.0309(2) Uani 1 1 d . . . . .
O8 O 0.79992(14) 0.45401(11) 0.73322(7) 0.0243(2) Uani 1 1 d D . . . .
O9 O 0.40986(13) 0.27201(11) 0.31666(6) 0.0250(2) Uani 1 1 d . . . . .
O10 O 0.09480(13) 0.18385(11) 0.31988(7) 0.0221(2) Uani 1 1 d D . . . .
N1 N 0.39974(18) 0.37066(15) 0.12949(9) 0.0232(3) Uani 1 1 d . . . . .
H1A H 0.482(3) 0.3035(19) 0.1423(12) 0.028 Uiso 1 1 d R . . . .
H1B H 0.348(2) 0.4171(18) 0.1838(13) 0.028 Uiso 1 1 d R . . . .
H1C H 0.477(3) 0.4433(19) 0.1096(12) 0.028 Uiso 1 1 d R . . . .
H1D H 0.296(3) 0.3293(18) 0.0844(13) 0.028 Uiso 1 1 d R . . . .
N2 N -0.19118(18) 0.34509(16) 0.38700(9) 0.0268(3) Uani 1 1 d . . . . .
H2C H -0.133(3) 0.433(2) 0.3759(13) 0.032 Uiso 1 1 d R . . . .
H2D H -0.121(3) 0.272(2) 0.3608(13) 0.032 Uiso 1 1 d R . . . .
H2E H -0.322(3) 0.3220(19) 0.3583(13) 0.032 Uiso 1 1 d R . . . .
H2F H -0.184(3) 0.3551(19) 0.4543(14) 0.032 Uiso 1 1 d R . . . .
C1 C -0.02831(19) 0.31485(14) -0.10232(9) 0.0190(3) Uani 1 1 d . . . . .
H1 H -0.1340 0.3761 -0.1085 0.023 Uiso 1 1 calc R . . . .
C2 C -0.09066(19) 0.16783(15) -0.17514(9) 0.0219(3) Uani 1 1 d . . . . .
H2A H -0.1114 0.1859 -0.2404 0.026 Uiso 1 1 calc R . . . .
H2B H 0.0149 0.1074 -0.1713 0.026 Uiso 1 1 calc R . . . .
C3 C -0.2817(2) 0.08556(15) -0.15436(9) 0.0231(3) Uani 1 1 d . . . . .
H3A H -0.3914 0.1397 -0.1667 0.028 Uiso 1 1 calc R . . . .
H3B H -0.3155 -0.0139 -0.1970 0.028 Uiso 1 1 calc R . . . .
C4 C -0.25622(19) 0.07181(15) -0.05080(9) 0.0214(3) Uani 1 1 d . . . . .
H4A H -0.1605 0.0053 -0.0410 0.026 Uiso 1 1 calc R . . . .
H4B H -0.3845 0.0283 -0.0356 0.026 Uiso 1 1 calc R . . . .
C5 C -0.18162(18) 0.22332(14) 0.01563(9) 0.0186(3) Uani 1 1 d . . . . .
H5A H -0.2836 0.2873 0.0083 0.022 Uiso 1 1 calc R . . . .
C6 C -0.15011(18) 0.20682(14) 0.11814(9) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.1638(2) 0.39774(15) -0.12012(9) 0.0221(3) Uani 1 1 d . . . . .
C8 C 0.30217(19) 0.26191(16) 0.46811(9) 0.0224(3) Uani 1 1 d . . . . .
H8A H 0.2318 0.3440 0.4928 0.027 Uiso 1 1 calc R . . . .
C9 C 0.2157(2) 0.1281(2) 0.50210(11) 0.0392(4) Uani 1 1 d . . . . .
H9A H 0.2817 0.0442 0.4786 0.047 Uiso 1 1 calc R . . . .
H9B H 0.0728 0.0997 0.4763 0.047 Uiso 1 1 calc R . . . .
C10 C 0.2443(2) 0.1625(2) 0.61128(11) 0.0409(4) Uani 1 1 d . . . . .
H10A H 0.1628 0.2365 0.6345 0.049 Uiso 1 1 calc R . . . .
H10B H 0.2008 0.0717 0.6336 0.049 Uiso 1 1 calc R . . . .
C11 C 0.4623(2) 0.22228(18) 0.65122(11) 0.0335(4) Uani 1 1 d . . . . .
H11A H 0.4780 0.2565 0.7214 0.040 Uiso 1 1 calc R . . . .
H11B H 0.5409 0.1427 0.6370 0.040 Uiso 1 1 calc R . . . .
C12 C 0.53818(19) 0.34939(16) 0.60737(9) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.4647 0.4318 0.6271 0.027 Uiso 1 1 calc R . . . .
C13 C 0.75796(19) 0.40540(14) 0.64310(9) 0.0204(3) Uani 1 1 d . . . . .
C14 C 0.27350(18) 0.23781(14) 0.35967(9) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.049(4) 0.192(3) 0.207(2) 0.041(8) Uiso 0.66(3) 1 d D . P A 1
H10 H 0.073(9) 0.197(7) 0.265(2) 0.041(8) Uiso 0.34(3) 1 d D . P A 2
H5 H 0.028(4) 0.458(3) -0.2191(18) 0.028(7) Uiso 0.69(3) 1 d D . P B 1
H8 H 0.921(5) 0.450(6) 0.754(4) 0.028(7) Uiso 0.31(3) 1 d D . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4294(15) . ?
O1 C5 1.4369(15) . ?
O2 C6 1.2996(16) . ?
O2 H2 0.83(3) . ?
O3 C6 1.2213(16) . ?
O4 C7 1.2171(17) . ?
O5 C7 1.3143(16) . ?
O5 H5 0.87(2) . ?
O6 C8 1.4288(15) . ?
O6 C12 1.4264(16) . ?
O7 C13 1.2372(17) . ?
O8 C13 1.2757(16) . ?
O8 H8 0.86(3) . ?
O9 C14 1.2306(16) . ?
O10 C14 1.2822(15) . ?
O10 H10 0.83(3) . ?
N1 H1A 0.936(18) . ?
N1 H1B 0.956(18) . ?
N1 H1C 0.920(18) . ?
N1 H1D 0.893(18) . ?
N2 H2C 0.915(19) . ?
N2 H2D 0.943(19) . ?
N2 H2E 0.924(19) . ?
N2 H2F 0.955(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.5300(18) . ?
C1 C7 1.5162(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5250(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5214(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5287(18) . ?
C5 H5A 1.0000 . ?
C5 C6 1.5155(18) . ?
C8 H8A 1.0000 . ?
C8 C9 1.509(2) . ?
C8 C14 1.5249(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.528(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.518(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.5237(18) . ?

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 O1 C5 110.38(9) . . ?
C6 O2 H2 114(2) . . ?
C7 O5 H5 113.3(17) . . ?
C12 O6 C8 111.25(10) . . ?
C13 O8 H8 112(4) . . ?
C14 O10 H10 112(4) . . ?
H1A N1 H1B 114.0(15) . . ?
H1A N1 H1C 106.2(14) . . ?
H1A N1 H1D 112.7(15) . . ?
H1B N1 H1C 107.6(14) . . ?
H1B N1 H1D 106.5(14) . . ?
H1C N1 H1D 109.8(15) . . ?
H2C N2 H2D 107.4(15) . . ?
H2C N2 H2E 110.2(16) . . ?
H2C N2 H2F 108.3(15) . . ?
H2D N2 H2E 109.9(15) . . ?
H2D N2 H2F 111.4(15) . . ?
H2E N2 H2F 109.6(15) . . ?
O1 C1 H1 109.0 . . ?
O1 C1 C2 111.18(10) . . ?
O1 C1 C7 108.19(10) . . ?
C2 C1 H1 109.0 . . ?
C7 C1 H1 109.0 . . ?
C7 C1 C2 110.46(11) . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 C1 109.33(11) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.79(10) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.34(11) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
O1 C5 C4 111.08(10) . . ?
O1 C5 H5A 108.9 . . ?
O1 C5 C6 109.54(10) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 C4 109.60(10) . . ?
C6 C5 H5A 108.9 . . ?
O2 C6 C5 114.14(11) . . ?
O3 C6 O2 125.42(12) . . ?
O3 C6 C5 120.35(11) . . ?
O4 C7 O5 121.18(12) . . ?
O4 C7 C1 123.00(12) . . ?
O5 C7 C1 115.80(11) . . ?
O6 C8 H8A 107.5 . . ?
O6 C8 C9 111.41(11) . . ?
O6 C8 C14 109.58(10) . . ?
C9 C8 H8A 107.5 . . ?
C9 C8 C14 112.97(12) . . ?
C14 C8 H8A 107.5 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.84(13) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 C9 109.71(13) . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.25(12) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
O6 C12 C11 111.98(11) . . ?
O6 C12 H12 108.3 . . ?
O6 C12 C13 108.92(10) . . ?
C11 C12 H12 108.3 . . ?
C11 C12 C13 110.79(11) . . ?
C13 C12 H12 108.3 . . ?
O7 C13 O8 124.61(12) . . ?
O7 C13 C12 121.40(12) . . ?
O8 C13 C12 113.98(11) . . ?
O9 C14 O10 124.58(12) . . ?
O9 C14 C8 122.05(11) . . ?
O10 C14 C8 113.34(11) . . ?

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
N2 H2C O7 0.915(19) 2.096(19) 2.8928(17) 144.9(15) 2_666
N2 H2D O10 0.943(19) 1.91(2) 2.8103(16) 159.4(15) .
N2 H2E O9 0.924(19) 1.839(19) 2.7578(15) 172.3(16) 1_455
N2 H2F O7 0.955(19) 1.875(19) 2.8152(16) 167.8(15) 1_455
O2 H2 O10 0.83(3) 1.65(3) 2.4747(13) 176(3) .
O10 H10 O2 0.83(3) 1.65(3) 2.4747(13) 173(6) .
O5 H5 O8 0.87(2) 1.64(2) 2.5082(14) 179(3) 1_454
O8 H8 O5 0.86(3) 1.65(3) 2.5082(14) 172(6) 1_656

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
O1 C1 C2 C3 58.75(14) . . . . ?
O1 C1 C7 O4 18.93(18) . . . . ?
O1 C1 C7 O5 -162.69(11) . . . . ?
O1 C5 C6 O2 -25.26(15) . . . . ?
O1 C5 C6 O3 157.99(12) . . . . ?
O6 C8 C9 C10 57.98(18) . . . . ?
O6 C8 C14 O9 -7.58(18) . . . . ?
O6 C8 C14 O10 174.49(11) . . . . ?
O6 C12 C13 O7 -4.61(18) . . . . ?
O6 C12 C13 O8 175.67(11) . . . . ?
C1 O1 C5 C4 61.28(13) . . . . ?
C1 O1 C5 C6 -177.50(10) . . . . ?
C1 C2 C3 C4 -53.61(15) . . . . ?
C2 C1 C7 O4 -102.98(15) . . . . ?
C2 C1 C7 O5 75.40(15) . . . . ?
C2 C3 C4 C5 53.07(15) . . . . ?
C3 C4 C5 O1 -56.82(14) . . . . ?
C3 C4 C5 C6 -178.00(10) . . . . ?
C4 C5 C6 O2 96.85(13) . . . . ?
C4 C5 C6 O3 -79.91(15) . . . . ?
C5 O1 C1 C2 -62.56(13) . . . . ?
C5 O1 C1 C7 175.98(10) . . . . ?
C7 C1 C2 C3 178.88(11) . . . . ?
C8 O6 C12 C11 59.96(15) . . . . ?
C8 O6 C12 C13 -177.15(11) . . . . ?
C8 C9 C10 C11 -53.3(2) . . . . ?
C9 C8 C14 O9 -132.44(14) . . . . ?
C9 C8 C14 O10 49.63(17) . . . . ?
C9 C10 C11 C12 52.0(2) . . . . ?
C10 C11 C12 O6 -55.54(18) . . . . ?
C10 C11 C12 C13 -177.37(13) . . . . ?
C11 C12 C13 O7 119.00(15) . . . . ?
C11 C12 C13 O8 -60.73(16) . . . . ?
C12 O6 C8 C9 -61.27(15) . . . . ?
C12 O6 C8 C14 172.97(11) . . . . ?
C14 C8 C9 C10 -178.17(13) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 0 0.0662 -1.0000 0.0000 0.0000 0.2011 -0.1071 -0.0069
1 0 0 0.0592 1.0000 -0.0000 -0.0000 -0.2011 0.1071 0.0069
0 0 -1 0.0468 0.0000 -0.0000 -1.0000 0.0115 -0.0217 0.1071
0 0 1 0.0468 -0.0000 0.0000 1.0000 -0.0115 0.0217 -0.1071
0 -1 0 0.0415 0.0000 -1.0000 -0.0000 -0.0520 -0.1614 0.0114
0 1 0 0.0415 -0.0000 1.0000 0.0000 0.0520 0.1614 -0.0114

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Water
