# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1945782'
loop_
_audit_author_name
_audit_author_address
'Emmanouil Manos'
;University of Ioannina
Greece
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H14 Mg O11, H2 O'
_chemical_formula_sum            'C8 H16 Mg O12'
_chemical_formula_weight         328.52

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   10.1744(9)
_cell_length_b                   6.6857(6)
_cell_length_c                   10.4150(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.751(4)
_cell_angle_gamma                90
_cell_volume                     685.11(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6964
_cell_measurement_theta_min      2.022
_cell_measurement_theta_max      27.906

_exptl_crystal_description       ROD
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.99319
_exptl_transmission_factor_max   1.00000
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER APEX'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6964
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.022
_diffrn_reflns_theta_max         27.906
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1778
_reflns_number_gt                1349
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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
_computing_cell_refinement       BRUKER
_computing_data_reduction        BRUKER
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
 DIAMOND (Brandenburg, 2006)
 MERCURY (Bruno et al. 2002)
;
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+0.1247P] 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_number_reflns         1778
_refine_ls_number_parameters     177
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.0989
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.226
_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
Mg1 Mg 0.17120(7) 0.250000 0.88952(7) 0.0188(2) Uani 1 2 d DS T P . .
O1 O 0.22867(18) 0.250000 1.08993(16) 0.0301(5) Uani 1 2 d S T P A .
O2 O 0.12131(17) 0.250000 1.25048(17) 0.0297(5) Uani 1 2 d S T P A .
O3 O 0.75422(17) 0.250000 1.71954(17) 0.0326(5) Uani 1 2 d S T P . .
O4 O 0.85275(19) 0.250000 1.55285(19) 0.0481(7) Uani 1 2 d DS T P . .
O5 O 0.25404(18) 0.250000 1.49134(17) 0.0406(6) Uani 1 2 d DS T P A .
O6 O 0.72056(17) 0.250000 1.31604(17) 0.0434(6) Uani 1 2 d DS T P . .
O1T O 0.11797(18) 0.250000 0.68672(17) 0.0464(7) Uani 1 2 d DS T P A .
O1W O 0.6043(2) 0.250000 1.9030(2) 0.0349(5) Uani 1 2 d DS T P . .
C1 C 0.2279(2) 0.250000 1.2085(2) 0.0197(5) Uani 1 2 d S T P . .
C2 C 0.3683(2) 0.250000 1.4468(2) 0.0198(5) Uani 1 2 d DS T P . .
C3 C 0.4940(2) 0.250000 1.5392(2) 0.0208(5) Uani 1 2 d S T P A .
H3 H 0.497856 0.250000 1.629427 0.025 Uiso 1 2 calc R U P . .
C4 C 0.6131(2) 0.250000 1.4986(2) 0.0198(5) Uani 1 2 d S T P . .
C5 C 0.6060(2) 0.250000 1.3620(2) 0.0226(5) Uani 1 2 d DS T P A .
C6 C 0.4813(2) 0.250000 1.2700(2) 0.0213(5) Uani 1 2 d S T P . .
H6 H 0.477374 0.250000 1.179810 0.026 Uiso 1 2 calc R U P A .
C7 C 0.3614(2) 0.250000 1.3113(2) 0.0170(5) Uani 1 2 d S T P A .
C8 C 0.7491(2) 0.250000 1.5983(2) 0.0263(6) Uani 1 2 d S T P A .
O2T O -0.0167(2) 0.1196(4) 0.8707(2) 0.0254(7) Uani 0.498(3) 1 d D . P A 1
O3T O 0.2669(3) -0.0102(4) 0.8880(2) 0.0356(8) Uani 0.498(3) 1 d D . P A 1
O2T' O 0.0844(3) -0.0320(4) 0.8971(2) 0.0309(7) Uani 0.502(3) 1 d D . P A 2
O3T' O 0.3486(3) 0.0849(4) 0.8841(3) 0.0284(7) Uani 0.502(3) 1 d D . P A 2
H1T H -0.0861(14) 0.174(3) 0.821(3) 0.034 Uiso 0.498(3) 1 d D U P A 1
H2T H -0.027(2) -0.002(2) 0.848(4) 0.034 Uiso 0.498(3) 1 d D U P A 1
H1T' H 0.032(3) -0.076(4) 0.8284(15) 0.034 Uiso 0.502(3) 1 d D U P A 2
H2T' H 0.056(3) -0.060(4) 0.9624(19) 0.034 Uiso 0.502(3) 1 d D U P A 2
H4T H 0.287(4) -0.084(3) 0.9549(17) 0.034 Uiso 0.498(3) 1 d D U P A 1
H3T H 0.246(3) -0.086(3) 0.8211(18) 0.034 Uiso 0.498(3) 1 d D U P A 1
H3T' H 0.328(2) -0.004(4) 0.825(3) 0.034 Uiso 0.502(3) 1 d D U P A 2
H4T' H 0.4082(19) 0.146(4) 0.880(4) 0.034 Uiso 0.502(3) 1 d D U P A 2
H1O5 H 0.1868(15) 0.250000 1.4210(16) 0.034 Uiso 1 2 d DS U P . .
H1O6 H 0.7904(13) 0.250000 1.3805(14) 0.034 Uiso 1 2 d DS U P . .
H1W H 0.649(3) 0.250000 1.845(2) 0.034 Uiso 1 2 d DS U P . .
H2W H 0.619(4) 0.136(3) 1.939(3) 0.034 Uiso 0.5 1 d D U P . .
H1T1 H 0.0361(12) 0.250000 0.644(2) 0.034 Uiso 1 2 d DS U P . .
H1T2 H 0.163(2) 0.250000 0.631(2) 0.034 Uiso 1 2 d DS U P . .


_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
Mg1 O3T 1.996(3) . ?
Mg1 O3T 1.996(3) 4_565 ?
Mg1 O1 2.0192(17) . ?
Mg1 O1T 2.0425(18) . ?
Mg1 O2T 2.064(2) 4_565 ?
Mg1 O2T 2.064(2) . ?
Mg1 O2T' 2.092(3) 4_565 ?
Mg1 O2T' 2.092(3) . ?
Mg1 O3T' 2.128(2) . ?
Mg1 O3T' 2.128(2) 4_565 ?
O1 C1 1.237(3) . ?
O2 C1 1.268(3) . ?
O3 C8 1.251(3) . ?
O4 C8 1.261(3) . ?
O5 C2 1.357(3) . ?
O6 C5 1.368(3) . ?
C1 C7 1.501(3) . ?
C2 C3 1.391(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.406(3) . ?
C4 C8 1.503(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.393(3) . ?
O2T O2T 1.744(6) 4_565 ?

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
O3T Mg1 O3T 121.3(2) . 4_565 ?
O3T Mg1 O1 89.70(8) . . ?
O3T Mg1 O1 89.70(8) 4_565 . ?
O3T Mg1 O1T 89.61(8) . . ?
O3T Mg1 O1T 89.61(8) 4_565 . ?
O1 Mg1 O1T 178.60(8) . . ?
O3T Mg1 O2T 144.02(13) . 4_565 ?
O3T Mg1 O2T 94.17(13) 4_565 4_565 ?
O1 Mg1 O2T 96.62(8) . 4_565 ?
O1T Mg1 O2T 84.65(8) . 4_565 ?
O3T Mg1 O2T 94.17(13) . . ?
O3T Mg1 O2T 144.02(13) 4_565 . ?
O1 Mg1 O2T 96.63(8) . . ?
O1T Mg1 O2T 84.65(8) . . ?
O2T Mg1 O2T 49.97(16) 4_565 . ?
O3T Mg1 O2T' 175.93(13) . 4_565 ?
O3T Mg1 O2T' 54.98(13) 4_565 4_565 ?
O1 Mg1 O2T' 88.56(7) . 4_565 ?
O1T Mg1 O2T' 92.05(7) . 4_565 ?
O2T Mg1 O2T' 39.93(11) 4_565 4_565 ?
O2T Mg1 O2T' 89.69(11) . 4_565 ?
O1 Mg1 O2T' 88.56(7) . . ?
O1T Mg1 O2T' 92.05(7) . . ?
O2T' Mg1 O2T' 128.63(16) 4_565 . ?
O1 Mg1 O3T' 90.17(9) . . ?
O1T Mg1 O3T' 88.62(9) . . ?
O2T' Mg1 O3T' 146.87(12) 4_565 . ?
O2T' Mg1 O3T' 84.42(11) . . ?
O3T Mg1 O3T' 91.91(15) . 4_565 ?
O3T Mg1 O3T' 29.44(11) 4_565 4_565 ?
O1 Mg1 O3T' 90.17(9) . 4_565 ?
O1T Mg1 O3T' 88.62(9) . 4_565 ?
O2T Mg1 O3T' 123.32(11) 4_565 4_565 ?
O2T Mg1 O3T' 170.89(11) . 4_565 ?
O2T' Mg1 O3T' 84.42(11) 4_565 4_565 ?
O2T' Mg1 O3T' 146.87(12) . 4_565 ?
O3T' Mg1 O3T' 62.47(17) . 4_565 ?
C1 O1 Mg1 163.37(17) . . ?
O1 C1 O2 124.6(2) . . ?
O1 C1 C7 118.5(2) . . ?
O2 C1 C7 116.9(2) . . ?
O5 C2 C3 118.71(19) . . ?
O5 C2 C7 121.24(19) . . ?
C3 C2 C7 120.1(2) . . ?
C4 C3 C2 120.8(2) . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 C8 120.9(2) . . ?
C5 C4 C8 120.0(2) . . ?
O6 C5 C6 118.12(19) . . ?
O6 C5 C4 121.7(2) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 120.5(2) . . ?
C6 C7 C2 119.34(19) . . ?
C6 C7 C1 118.96(19) . . ?
C2 C7 C1 121.7(2) . . ?
O3 C8 O4 123.7(2) . . ?
O3 C8 C4 119.5(2) . . ?
O4 C8 C4 116.8(2) . . ?
O2T O2T Mg1 65.01(8) 4_565 . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.107

