# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_MBS-Cinn
_database_code_depnum_ccdc_archive 'CCDC 1945762'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;The University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_nottingham_internal_coll_name   OGPALA
_nottingham_internal_coll_number 17024
_nottingham_internal_coll_client GPA/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '30.00, 120.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxga2
_nottingham_internal_coll_date   12/05/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 25/05/2017
_nottingham_internal_process_user pcxga2
_nottingham_internal_solution_date 14/06/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 20/06/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 20/06/2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
;
 The absolute configuration of the structure is determined by reference
 to the D-sorbitol starting material. Refinement of each configuration
 gives the same R1 value. Refinement of the opposite configuration
 gives a lower Flack parameter however this is not significant given
 the large uncertainity of the refined value.

 The crystal was weakly diffracting with a resolution limit of 0.9 A.
 The data was truncated to a resolution of 0.9 A resulting in a low
 data to parameter ratio, necessitating application of a large number
 of restraints to the cinnamyl moieties of the two residues (DFIX, DANG
 and FLAT). Rigid bond restraints were applied to the anisotropic
 displacement parameters of all atoms in the structure (RIGU).

 The cinnamyl moiety of residue B is disordered over two conformations
 the occupancies of which have been refined and constrained to sum to
 unity, having values of 0.65(4) and 0.35(4). The anisotropic
 displacement parameters of the disordered moieties have been restrained
 to be similar (SIMU). Geometric restraints applied to the 1,2 and 1,3
 distances in the disordered moieties were calculated using Grade Web
 Server v1.104. The anisotropic displacement parameters of disordered
 atoms C17C/B and C18C/B have been restrained to have more isotropic
 character (ISOR).

 Hydrogen atoms bound to carbon atoms in the structure were geometrically
 placed and refined using a riding model. Hydroxyl hydrogen atoms were
 not observed in the electron denisty map and are geometrically placed
 to donate hydrogen bonds to appropriate acceptors. Geometric placement
 of hydroxyl atoms on O4B and O12B clashed with hydrogen atoms of
 adjacent hydroxyl groups and were omitted from the model. Their correct
 positions could not be determined from the electron denisty map and it
 is likely that many of the hydrogen bonds are in fact disordered with
 roles of donors and acceptors interchangeable. The omitted hydrogen
 atoms are included in the unit cell contents.
;
_vrf_PLAT020_MBS-Cinn            
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.124 Report
RESPONSE: ...
;
_vrf_PLAT041_MBS-Cinn            
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE:
 Hydrogen atoms for two hydroxy groups were not observed in the electron density
 map and not included in the model, however they were included in the unit cell
 contents and derived values.
;
_vrf_PLAT043_MBS-Cinn            
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       2.02 Check 
RESPONSE:
 Hydrogen atoms for two hydroxy groups were not observed in the electron density
 map and not included in the model, however they were included in the unit cell
 contents and derived values.
;
_vrf_PLAT068_MBS-Cinn            
;
PROBLEM: Reported F000 Differs from Calcd (or Missing)...     Please Check 
RESPONSE:
 Hydrogen atoms for two hydroxy groups were not observed in the electron density
 map and not included in the model, however they were included in the unit cell
 contents and derived values.
;
_vrf_PLAT089_MBS-Cinn            
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.89 Note  
RESPONSE:
 The crystal was weakly diffracting with a diffraction limit of 0.9 A. Where
 appropriate restraints have been applied to the displacement parameters and
 geometries of the atoms to aid refinement and compensate for the low data
 to parameter ratio.
;
_vrf_PLAT340_MBS-Cinn            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01435 Ang.  
RESPONSE:
 The crystal was weakly diffracting with a diffraction limit of 0.9 A. Where
 appropriate restraints have been applied to the displacement parameters and
 geometries of the atoms to aid refinement and compensate for the low data
 to parameter ratio.
;
_vrf_PLAT411_MBS-Cinn            
;
PROBLEM: Short Inter H...H Contact  H1BA     ..H20B     .       2.12 Ang.  
RESPONSE:
 Hydrogen atom H20B is part of a disordered phenyl ring; the clash is likely
 a result of unmodelled complementary disorder in the other moiety.
;
_vrf_PLAT907_MBS-Cinn            
;
PROBLEM: Flack x > 0.5, Structure Needs to be Inverted? .       1.00 Check 
RESPONSE:
 The absolute configuration of the structure is determined by reference
 to the D-sorbitol starting material. Refinement of each configuration
 gives the same R1 value. Refinement of the opposite configuration
 gives a lower Flack parameter however this is not significant given
 the large uncertainity of the refined value.
;
_vrf_RINTA01_MBS-Cinn            
;
PROBLEM: The value of Rint is greater than 0.12
RESPONSE:
 The crystal was weakly diffracting with a diffraction limit of 0.9 A. Where
 appropriate restraints have been applied to the displacement parameters and
 geometries of the atoms to aid refinement.
;
_vrf_STRVA01_MBS-Cinn            
;
PROBLEM: Chirality of atom sites is inverted?
RESPONSE:
 The absolute configuration of the structure is determined by reference
 to the D-sorbitol starting material. Refinement of each configuration
 gives the same R1 value. Refinement of the opposite configuration
 gives a lower Flack parameter however this is not significant given
 the large uncertainity of the refined value.
;
_vrf_THETM01_MBS-Cinn            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE:
 The crystal was weakly diffracting with a diffraction limit of 0.9 A.
;
_audit_creation_date             2019-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C15 H20 O6), 0.5(C15 H18 O6)'
_chemical_formula_sum            'C15 H20 O6'
_chemical_formula_weight         296.31
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H19 O6'
_chemical_oxdiff_usercomment     
'OGPALA #17024 GVB-1351 IN FOMBLIM ON A MICROMOUNT FOR GPA/DBA'
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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.7673(11)
_cell_length_b                   9.5601(19)
_cell_length_c                   31.386(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.31(2)
_cell_angle_gamma                90
_cell_volume                     1429.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1922
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.1210
_cell_measurement_theta_min      4.8160
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 -4 0.0214
0 0 1 0.0010
2 5 4 0.0728
0 0 -1 0.0225
-3 0 4 0.1132
0 5 4 0.0010

_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.022
loop_
_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
0.0074 -4.9627 -3.7492 0.1002 -0.3467 -0.7383
0.0020 -0.0135 0.9979 0.0466 0.0101 0.0114
1.9851 4.9689 3.6433 -0.1282 0.9291 0.4655
-0.0020 0.0135 -0.9979 -0.0466 -0.0101 -0.0114
-2.9808 -0.0635 4.1504 0.2286 -0.8333 0.4546
-0.0074 4.9627 3.7492 -0.1002 0.3467 0.7383

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1240
_diffrn_reflns_av_unetI/netI     0.1544
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8745
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        58.931
_diffrn_reflns_theta_max         58.931
_diffrn_reflns_theta_min         4.229
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  31.00   1.00   30.00    --  -38.50  38.00 -30.00   25
  2  ω    -49.00  32.00   1.00   30.00    --  -38.50  38.00-150.00   81
  3  ω     21.00  65.00   1.00   30.00    --   43.08  38.00 150.00   44
  4  ω      5.00  87.00   1.00   30.00    --   43.08-125.00 -60.00   82
  5  ω     13.00 117.00   1.00   30.00    --   43.08  77.00-180.00  104
  6  ω     32.00 136.00   1.00  120.00    --  104.50 -77.00-120.00  104
  7  ω     33.00 104.00   1.00  120.00    --  104.50-125.00-150.00   71
  8  ω     73.00 136.00   1.00  120.00    --  104.50  77.00 150.00   63
  9  ω     77.00 104.00   1.00  120.00    --  104.50  61.00 120.00   27
 10  ω    141.00 172.00   1.00  120.00    --  104.50  45.00-150.00   31
 11  ω     85.00 160.00   1.00  120.00    --  104.50  61.00-180.00   75
 12  ω     78.00 103.00   1.00  120.00    --  104.50  61.00  90.00   25
 13  ω     78.00 127.00   1.00  120.00    --  104.50  61.00 150.00   49
 14  ω     73.00 102.00   1.00  120.00    --  104.50  77.00  90.00   29
 15  ω     46.00  97.00   1.00  120.00    --  104.50 -45.00 -30.00   51
 16  ω     57.00  84.00   1.00  120.00    --  104.50 -30.00   0.00   27
 17  ω    129.00 177.00   1.00  120.00    --  104.50  77.00 120.00   48
 18  ω     74.00  99.00   1.00  120.00    --  104.50  77.00 120.00   25
 19  ω    115.00 176.00   1.00  120.00    --  104.50  77.00  90.00   61
 20  ω    100.00 171.00   1.00  120.00    --  104.50  45.00  60.00   71
 21  ω     81.00 106.00   1.00  120.00    --  104.50  45.00  90.00   25
 22  ω     82.00 109.00   1.00  120.00    --  104.50  45.00 150.00   27
 23  ω     60.00  89.00   1.00  120.00    --  104.50 -30.00  30.00   29
 24  ω     40.00  71.00   1.00  120.00    --  104.50 -45.00  90.00   31
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0114626000
_diffrn_orient_matrix_UB_12      -0.0549525000
_diffrn_orient_matrix_UB_13      0.0460028000
_diffrn_orient_matrix_UB_21      0.2926554000
_diffrn_orient_matrix_UB_22      0.0624648000
_diffrn_orient_matrix_UB_23      0.0103597000
_diffrn_orient_matrix_UB_31      -0.1366117000
_diffrn_orient_matrix_UB_32      0.1383456000
_diffrn_orient_matrix_UB_33      0.0135340000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2892
_reflns_number_total             4045
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 
;
 Flack x determined using 745 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     697
_refine_ls_R_factor_all          0.1156
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      0.980
_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)+(0.0863P)²+0.0156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2019
_refine_ls_wR_factor_ref         0.2243
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1AA(0.041) H1AB(0.041) H2A(0.06) H3A(0.029) H4A(0.047)
 H5A(0.028) H7A(0.029) H8A(0.05) H9A(0.029) H11C(0.034) H11D(0.034) H12A(0.051)
 H13A(0.028) H14C(0.03) H15A(0.034) H17A(0.04) H18A(0.042) H19A(0.048)
 H20A(0.048) H21A(0.045) H1BA(0.046) H1BB(0.046) H2B(0.059) H3B(0.035)
 H5B(0.033) H7B(0.032) H8B(0.047) H9B(0.035) H11A(0.037) H11B(0.037)
 H13B(0.034) H14B(0.035) H14A(0.035) H15B(0.045) H21B(0.056) H20B(0.068)
 H19B(0.056) H18B(0.056) H17B(0.047) H15C(0.043) H21C(0.056) H20C(0.061)
 H19C(0.062) H18C(0.051) H17C(0.048)
 Fixed X: H1AA(0.451788) H1AB(0.69351) H2A(0.363267) H3A(0.331452)
 H4A(0.817149) H5A(0.873004) H7A(0.921497) H8A(0.590975) H9A(1.105617)
 H11C(0.868886) H11D(1.101998) H12A(1.400355) H13A(0.84619) H14C(0.333068)
 H15A(0.646186) H17A(0.124405) H18A(-0.142387) H19A(-0.124605) H20A(0.17681)
 H21A(0.447688) H1BA(1.031028) H1BB(1.340626) H2B(1.15156) H3B(0.916424)
 H5B(1.18289) H7B(1.088104) H8B(0.586787) H9B(0.986319) H11A(0.623695)
 H11B(0.517669) H13B(0.906164) H14B(0.397394) H14A(0.379636) H15B(0.639015)
 H21B(0.449929) H20B(0.172317) H19B(-0.122867) H18B(-0.147642) H17B(0.134464)
 H15C(0.663741) H21C(0.473021) H20C(0.144993) H19C(-0.204772) H18C(-0.237506)
 H17C(0.076371)
 Fixed Y: H1AA(1.333983) H1AB(1.397535) H2A(1.458037) H3A(1.173855)
 H4A(1.203282) H5A(1.15924) H7A(1.002541) H8A(0.881764) H9A(0.934367)
 H11C(0.680616) H11D(0.760417) H12A(0.684592) H13A(1.028268) H14C(0.876979)
 H15A(1.059747) H17A(0.793284) H18A(0.750783) H19A(0.905448) H20A(1.097315)
 H21A(1.137206) H1BA(0.354192) H1BB(0.418902) H2B(0.212566) H3B(0.477804)
 H5B(0.655907) H7B(0.801909) H8B(0.68802) H9B(0.898056) H11A(1.064093)
 H11B(0.974851) H13B(0.721499) H14B(0.565156) H14A(0.577556) H15B(0.773367)
 H21B(0.84311) H20B(0.801084) H19B(0.608843) H18B(0.455832) H17B(0.494941)
 H15C(0.733411) H21C(0.759654) H20C(0.70718) H19C(0.542832) H18C(0.436034)
 H17C(0.494706)
 Fixed Z: H1AA(0.856598) H1AB(0.828186) H2A(0.781488) H3A(0.79774)
 H4A(0.764955) H5A(0.841047) H7A(0.783826) H8A(0.763102) H9A(0.851666)
 H11C(0.818642) H11D(0.792407) H12A(0.835651) H13A(0.906544) H14C(0.922227)
 H15A(0.972093) H17A(0.979865) H18A(1.038895) H19A(1.096634) H20A(1.096095)
 H21A(1.037595) H1BA(0.652506) H1BB(0.654549) H2B(0.699852) H3B(0.714292)
 H5B(0.654099) H7B(0.708139) H8B(0.712661) H9B(0.642795) H11A(0.653745)
 H11B(0.69333) H13B(0.594887) H14B(0.582648) H14A(0.585469) H15B(0.535759)
 H21B(0.468025) H20B(0.406732) H19B(0.402201) H18B(0.459911) H17B(0.521037)
 H15C(0.527222) H21C(0.457264) H20C(0.402541) H19C(0.413054) H18C(0.479299)
 H17C(0.535071)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C1A C 0.508(3) 1.3513(12) 0.8270(3) 0.034(3) Uani 1 1 d . U . . .
H1AA H 0.451788 1.333983 0.856598 0.041 Uiso 1 1 calc R . . . .
H1AB H 0.693510 1.397535 0.828186 0.041 Uiso 1 1 calc R . . . .
O2A O 0.3084(18) 1.4383(9) 0.8059(3) 0.0402(19) Uani 1 1 d . U . . .
H2A H 0.363267 1.458037 0.781488 0.060 Uiso 1 1 calc GR . . . .
C3A C 0.525(2) 1.2127(11) 0.8029(3) 0.024(2) Uani 1 1 d . U . . .
H3A H 0.331452 1.173855 0.797740 0.029 Uiso 1 1 calc R . . . .
O4A O 0.6521(16) 1.2342(9) 0.7634(2) 0.0311(17) Uani 1 1 d . U . . .
H4A H 0.817149 1.203282 0.764955 0.047 Uiso 1 1 calc GR . . . .
C5A C 0.700(2) 1.1104(11) 0.8296(3) 0.024(2) Uani 1 1 d . U . . .
H5A H 0.873004 1.159240 0.841047 0.028 Uiso 1 1 calc R . . . .
O6A O 0.5284(14) 1.0723(8) 0.8648(2) 0.0251(15) Uani 1 1 d . U . . .
C7A C 0.787(2) 0.9772(11) 0.8063(3) 0.025(2) Uani 1 1 d . U . . .
H7A H 0.921497 1.002541 0.783826 0.029 Uiso 1 1 calc R . . . .
O8A O 0.5500(16) 0.9145(9) 0.7869(2) 0.0331(17) Uani 1 1 d . U . . .
H8A H 0.590975 0.881764 0.763102 0.050 Uiso 1 1 calc GR . . . .
C9A C 0.937(2) 0.8837(12) 0.8395(3) 0.024(2) Uani 1 1 d . U . . .
H9A H 1.105617 0.934367 0.851666 0.029 Uiso 1 1 calc R . . . .
O10A O 0.7527(15) 0.8541(8) 0.8732(2) 0.0270(16) Uani 1 1 d . U . . .
C11A C 1.031(2) 0.7452(12) 0.8213(3) 0.028(2) Uani 1 1 d . U . . .
H11C H 0.868886 0.680616 0.818642 0.034 Uiso 1 1 calc R . . . .
H11D H 1.101998 0.760417 0.792407 0.034 Uiso 1 1 calc R . . . .
O12A O 1.2482(16) 0.6836(9) 0.8482(2) 0.0342(17) Uani 1 1 d . U . . .
H12A H 1.400355 0.684592 0.835651 0.051 Uiso 1 1 calc GR . . . .
C13A C 0.675(2) 0.9807(11) 0.8939(3) 0.023(2) Uani 1 1 d . U . . .
H13A H 0.846190 1.028268 0.906544 0.028 Uiso 1 1 calc R . . . .
C14A C 0.478(2) 0.9428(11) 0.9286(3) 0.025(2) Uani 1 1 d D U . . .
H14C H 0.333068 0.876979 0.922227 0.030 Uiso 1 1 calc R . . . .
C15A C 0.497(2) 0.9956(12) 0.9668(3) 0.028(2) Uani 1 1 d D U . . .
H15A H 0.646186 1.059747 0.972093 0.034 Uiso 1 1 calc R . . . .
C16A C 0.3178(18) 0.9694(10) 1.0027(3) 0.028(2) Uani 1 1 d D U . . .
C17A C 0.137(2) 0.8551(11) 1.0036(3) 0.033(2) Uani 1 1 d D U . . .
H17A H 0.124405 0.793284 0.979865 0.040 Uiso 1 1 calc R . . . .
C18A C -0.023(2) 0.8304(12) 1.0385(3) 0.035(3) Uani 1 1 d D U . . .
H18A H -0.142387 0.750783 1.038895 0.042 Uiso 1 1 calc R . . . .
C19A C -0.011(2) 0.9215(12) 1.0729(3) 0.040(3) Uani 1 1 d D U . . .
H19A H -0.124605 0.905448 1.096634 0.048 Uiso 1 1 calc R . . . .
C20A C 0.166(2) 1.0351(12) 1.0725(3) 0.040(3) Uani 1 1 d D U . . .
H20A H 0.176810 1.097315 1.096095 0.048 Uiso 1 1 calc R . . . .
C21A C 0.327(2) 1.0582(12) 1.0376(3) 0.037(3) Uani 1 1 d D U . . .
H21A H 0.447688 1.137206 1.037595 0.045 Uiso 1 1 calc R . . . .
C1B C 1.186(3) 0.3860(12) 0.6721(4) 0.038(3) Uani 1 1 d . U . . .
H1BA H 1.031028 0.354192 0.652506 0.046 Uiso 1 1 calc R . . . .
H1BB H 1.340626 0.418902 0.654549 0.046 Uiso 1 1 calc R . . . .
O2B O 1.2828(18) 0.2703(9) 0.6975(3) 0.0392(19) Uani 1 1 d . U . . .
H2B H 1.151560 0.212566 0.699852 0.059 Uiso 1 1 calc GR . . . .
C3B C 1.084(2) 0.5066(12) 0.6982(3) 0.029(2) Uani 1 1 d . U . . .
H3B H 0.916424 0.477804 0.714292 0.035 Uiso 1 1 calc R . . . .
O4B O 1.3034(15) 0.5527(9) 0.7270(2) 0.0325(17) Uani 1 1 d . U . . .
C5B C 1.012(2) 0.6315(12) 0.6700(3) 0.027(2) Uani 1 1 d . U . . .
H5B H 1.182890 0.655907 0.654099 0.033 Uiso 1 1 calc R . . . .
O6B O 0.7965(14) 0.5861(8) 0.6389(2) 0.0286(15) Uani 1 1 d . U . . .
C7B C 0.919(2) 0.7621(12) 0.6928(3) 0.027(2) Uani 1 1 d . U . . .
H7B H 1.088104 0.801909 0.708139 0.032 Uiso 1 1 calc R . . . .
O8B O 0.7168(15) 0.7376(9) 0.7234(2) 0.0312(16) Uani 1 1 d . U . . .
H8B H 0.586787 0.688020 0.712661 0.047 Uiso 1 1 calc GR . . . .
C9B C 0.821(2) 0.8691(12) 0.6593(3) 0.029(2) Uani 1 1 d . U . . .
H9B H 0.986319 0.898056 0.642795 0.035 Uiso 1 1 calc R . . . .
O10B O 0.6134(15) 0.8105(8) 0.6303(2) 0.0289(16) Uani 1 1 d . U . . .
C11B C 0.685(2) 1.0008(11) 0.6773(3) 0.030(2) Uani 1 1 d . U . . .
H11A H 0.623695 1.064093 0.653745 0.037 Uiso 1 1 calc R . . . .
H11B H 0.517669 0.974851 0.693330 0.037 Uiso 1 1 calc R . . . .
O12B O 0.8858(16) 1.0697(9) 0.7049(2) 0.0354(17) Uani 1 1 d . U . . .
C13B C 0.732(2) 0.6922(12) 0.6091(3) 0.028(2) Uani 1 1 d . U . . .
H13B H 0.906164 0.721499 0.594887 0.034 Uiso 1 1 calc R . . . .
C14B C 0.520(2) 0.6399(12) 0.5763(3) 0.029(2) Uani 1 1 d D U . . .
H14B H 0.397394 0.565156 0.582648 0.035 Uiso 0.66(4) 1 calc R . P A 1
H14A H 0.379636 0.577556 0.585469 0.035 Uiso 0.34(4) 1 calc R . P A 2
C15B C 0.509(5) 0.699(2) 0.5390(5) 0.038(5) Uani 0.66(4) 1 d D U P A 1
H15B H 0.639015 0.773367 0.535759 0.045 Uiso 0.66(4) 1 calc R . P A 1
C16B C 0.327(4) 0.671(2) 0.5008(5) 0.040(4) Uani 0.66(4) 1 d D U P A 1
C21B C 0.332(4) 0.763(3) 0.4665(5) 0.047(5) Uani 0.66(4) 1 d D U P A 1
H21B H 0.449929 0.843110 0.468025 0.056 Uiso 0.66(4) 1 calc R . P A 1
C20B C 0.165(4) 0.738(3) 0.4302(5) 0.056(6) Uani 0.66(4) 1 d D U P A 1
H20B H 0.172317 0.801084 0.406732 0.068 Uiso 0.66(4) 1 calc R . P A 1
C19B C -0.011(5) 0.625(2) 0.4274(6) 0.047(6) Uani 0.66(4) 1 d D U P A 1
H19B H -0.122867 0.608843 0.402201 0.056 Uiso 0.66(4) 1 calc R . P A 1
C18B C -0.024(5) 0.534(2) 0.4614(7) 0.046(6) Uani 0.66(4) 1 d D U P A 1
H18B H -0.147642 0.455832 0.459911 0.056 Uiso 0.66(4) 1 calc R . P A 1
C17B C 0.144(5) 0.558(2) 0.4977(6) 0.039(5) Uani 0.66(4) 1 d D U P A 1
H17B H 0.134464 0.494941 0.521037 0.047 Uiso 0.66(4) 1 calc R . P A 1
C15C C 0.516(8) 0.674(4) 0.5358(8) 0.036(7) Uani 0.34(4) 1 d D U P A 2
H15C H 0.663741 0.733411 0.527222 0.043 Uiso 0.34(4) 1 calc R . P A 2
C16C C 0.309(6) 0.632(4) 0.5021(7) 0.038(7) Uani 0.34(4) 1 d D U P A 2
C21C C 0.327(7) 0.695(5) 0.4621(9) 0.047(8) Uani 0.34(4) 1 d D U P A 2
H21C H 0.473021 0.759654 0.457264 0.056 Uiso 0.34(4) 1 calc R . P A 2
C20C C 0.134(8) 0.662(5) 0.4294(8) 0.050(9) Uani 0.34(4) 1 d D U P A 2
H20C H 0.144993 0.707180 0.402541 0.061 Uiso 0.34(4) 1 calc R . P A 2
C19C C -0.075(8) 0.566(5) 0.4357(10) 0.052(9) Uani 0.34(4) 1 d D U P A 2
H19C H -0.204772 0.542832 0.413054 0.062 Uiso 0.34(4) 1 calc R . P A 2
C18C C -0.094(7) 0.503(4) 0.4749(11) 0.043(9) Uani 0.34(4) 1 d D U P A 2
H18C H -0.237506 0.436034 0.479299 0.051 Uiso 0.34(4) 1 calc R . P A 2
C17C C 0.094(7) 0.537(4) 0.5079(9) 0.040(8) Uani 0.34(4) 1 d D U P A 2
H17C H 0.076371 0.494706 0.535071 0.048 Uiso 0.34(4) 1 calc R . P A 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
C1A O2A 1.408(14) . ?
C1A C3A 1.529(15) . ?
C3A O4A 1.418(13) . ?
C3A C5A 1.517(15) . ?
C5A O6A 1.449(12) . ?
C5A C7A 1.534(13) . ?
O6A C13A 1.429(12) . ?
C7A O8A 1.397(13) . ?
C7A C9A 1.530(14) . ?
C9A O10A 1.431(12) . ?
C9A C11A 1.517(15) . ?
O10A C13A 1.429(12) . ?
C11A O12A 1.437(13) . ?
C13A C14A 1.512(14) . ?
C14A C15A 1.300(14) . ?
C15A C16A 1.460(12) . ?
C16A C17A 1.392(12) . ?
C16A C21A 1.387(12) . ?
C17A C18A 1.383(11) . ?
C18A C19A 1.387(13) . ?
C19A C20A 1.376(14) . ?
C20A C21A 1.380(11) . ?
C1B O2B 1.428(14) . ?
C1B C3B 1.506(15) . ?
C3B O4B 1.426(13) . ?
C3B C5B 1.518(15) . ?
C5B O6B 1.453(13) . ?
C5B C7B 1.514(15) . ?
O6B C13B 1.405(13) . ?
C7B O8B 1.407(13) . ?
C7B C9B 1.525(15) . ?
C9B O10B 1.431(13) . ?
C9B C11B 1.536(14) . ?
O10B C13B 1.438(13) . ?
C11B O12B 1.427(14) . ?
C13B C14B 1.497(15) . ?
C14B C15B 1.30(2) . ?
C14B C15C 1.31(3) . ?
C15B C16B 1.476(17) . ?
C16B C21B 1.395(15) . ?
C16B C17B 1.388(15) . ?
C21B C20B 1.384(14) . ?
C20B C19B 1.372(18) . ?
C19B C18B 1.379(17) . ?
C18B C17B 1.386(14) . ?
C15C C16C 1.47(2) . ?
C16C C21C 1.396(17) . ?
C16C C17C 1.387(17) . ?
C21C C20C 1.387(15) . ?
C20C C19C 1.375(19) . ?
C19C C18C 1.376(19) . ?
C18C C17C 1.3840(16) . ?

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
O2A C1A C3A 109.1(9) . . ?
O4A C3A C1A 109.8(8) . . ?
O4A C3A C5A 109.2(8) . . ?
C5A C3A C1A 109.0(9) . . ?
C3A C5A C7A 115.2(8) . . ?
O6A C5A C3A 105.4(8) . . ?
O6A C5A C7A 109.1(8) . . ?
C13A O6A C5A 111.4(7) . . ?
O8A C7A C5A 109.5(8) . . ?
O8A C7A C9A 113.2(9) . . ?
C9A C7A C5A 106.7(8) . . ?
O10A C9A C7A 109.6(7) . . ?
O10A C9A C11A 107.8(8) . . ?
C11A C9A C7A 112.9(8) . . ?
C13A O10A C9A 110.3(7) . . ?
O12A C11A C9A 110.6(8) . . ?
O6A C13A O10A 110.9(7) . . ?
O6A C13A C14A 107.7(8) . . ?
O10A C13A C14A 107.7(8) . . ?
C15A C14A C13A 123.3(10) . . ?
C14A C15A C16A 128.6(10) . . ?
C17A C16A C15A 122.1(8) . . ?
C21A C16A C15A 120.3(9) . . ?
C21A C16A C17A 117.6(8) . . ?
C18A C17A C16A 120.9(9) . . ?
C17A C18A C19A 120.2(9) . . ?
C20A C19A C18A 119.6(9) . . ?
C19A C20A C21A 119.7(9) . . ?
C20A C21A C16A 121.9(9) . . ?
O2B C1B C3B 113.3(9) . . ?
C1B C3B C5B 110.8(9) . . ?
O4B C3B C1B 109.7(9) . . ?
O4B C3B C5B 105.7(8) . . ?
O6B C5B C3B 107.1(8) . . ?
O6B C5B C7B 110.5(8) . . ?
C7B C5B C3B 115.8(8) . . ?
C13B O6B C5B 111.1(8) . . ?
C5B C7B C9B 108.3(9) . . ?
O8B C7B C5B 114.1(9) . . ?
O8B C7B C9B 112.6(9) . . ?
C7B C9B C11B 114.8(9) . . ?
O10B C9B C7B 111.1(8) . . ?
O10B C9B C11B 105.2(8) . . ?
C9B O10B C13B 109.1(8) . . ?
O12B C11B C9B 108.5(9) . . ?
O6B C13B O10B 109.9(8) . . ?
O6B C13B C14B 109.9(8) . . ?
O10B C13B C14B 108.3(8) . . ?
C15B C14B C13B 118.4(13) . . ?
C15C C14B C13B 124.4(19) . . ?
C14B C15B C16B 130.7(18) . . ?
C21B C16B C15B 118.8(14) . . ?
C17B C16B C15B 123.3(14) . . ?
C17B C16B C21B 117.9(12) . . ?
C20B C21B C16B 120.1(14) . . ?
C19B C20B C21B 121.0(14) . . ?
C20B C19B C18B 119.9(14) . . ?
C19B C18B C17B 119.2(14) . . ?
C18B C17B C16B 121.8(14) . . ?
C14B C15C C16C 128(3) . . ?
C21C C16C C15C 118(2) . . ?
C17C C16C C15C 124(2) . . ?
C17C C16C C21C 118.1(15) . . ?
C20C C21C C16C 120.5(17) . . ?
C19C C20C C21C 120.4(18) . . ?
C20C C19C C18C 119.8(17) . . ?
C19C C18C C17C 120.1(17) . . ?
C18C C17C C16C 121.1(17) . . ?

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
_geom_hbond_publ_flag
O2A H2A O4B 0.84 1.94 2.704(11) 149.9 1_465 yes
O8A H8A O8B 0.84 1.97 2.755(10) 155.8 . yes
O8B H8B O4B 0.84 1.94 2.653(10) 142.6 1_455 yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.428
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# 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_MBS-Van
_database_code_depnum_ccdc_archive 'CCDC 1945763'
loop_
_audit_author_name
_audit_author_address
'Stephen Argent'
;The University of Nottingham
United Kingdom
;
_audit_update_record             
;
2019-08-06 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_nottingham_internal_coll_name   OGPALB
_nottingham_internal_coll_number 17025
_nottingham_internal_coll_client GPA/DBA
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '6.00, 24.00'
_nottingham_internal_coll_frame_width 1.00
_nottingham_internal_coll_user   pcxga2
_nottingham_internal_coll_date   15/05/2017
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 25/05/2017
_nottingham_internal_process_user pcxga2
_nottingham_internal_solution_date 25/05/2017
_nottingham_internal_solution_user pcxga2
_nottingham_internal_refinement_date 20/06/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 2019
_nottingham_internal_validation_user pczspa
_nottingham_internal_archive_date ?
_refine_special_details          
'Hydrogen atoms attached to carbon atoms were observed in the electron density map before being geometrically placed and refined using a riding model. The positions of hydroxy hydrogen atoms H8, H8, H12 and H22 are refined with their O-H bond distances restrained to a target value of 0.84 A (DFIX). Hydroxy hydrogen atom H2 was geometrically placed and refined with a riding model (AFIX 147). The isotropic displacement parameters of the hydroxy hydrogen atoms are fixed at a value of 1.5 time Ueq of their parent oxygen atoms.'
_audit_creation_date             2019-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O8'
_chemical_formula_sum            'C14 H20 O8'
_chemical_formula_weight         316.30
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H20 O8'
_chemical_oxdiff_usercomment     
'OGPALB #17025 GVB-1352 IN FOMBLIM ON A MICROMOUNT FOR GPA/DBA'
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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.92283(14)
_cell_length_b                   4.60123(7)
_cell_length_c                   17.4539(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.9088(15)
_cell_angle_gamma                90
_cell_volume                     715.66(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7491
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.4150
_cell_measurement_theta_min      4.9530
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    1.035
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0410
5 0 -1 0.0040
-5 0 -3 0.0068
0 -3 -1 0.0936
0 3 2 0.0952
0 0 -1 0.0050

_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.026
loop_
_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
0.0009 0.0002 0.9997 0.0040 -0.0278 -0.0838
4.9986 -0.0017 -1.0006 -0.8573 0.1034 -0.0302
-5.0023 0.0009 -2.9983 0.8414 0.0079 0.3653
-0.0078 -2.9994 -1.0059 -0.1282 -0.9193 0.3937
0.0087 2.9996 2.0056 0.1322 0.8915 -0.4775
-0.0009 -0.0002 -0.9997 -0.0040 0.0278 0.0838

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9752
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.532
_diffrn_reflns_theta_min         4.963
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  34.00   1.00    6.00    --  -38.50  38.00 -60.00   84
  2  ω    -65.00  32.00   1.00    6.00    --  -38.50  57.00  60.00   97
  3  ω     20.00 115.00   1.00    6.00    --   42.83  38.00-120.00   95
  4  ω     11.00 117.00   1.00    6.00    --   42.83  77.00 120.00  106
  5  ω     33.00  98.00   1.00   24.00    --  104.50 -45.00  30.00   65
  6  ω     81.00 178.00   1.00   24.00    --  104.50  30.00 -90.00   97
  7  ω     59.00 178.00   1.00   24.00    --  104.50  15.00   0.00  119
  8  ω     77.00 175.00   1.00   24.00    --  104.50  61.00  90.00   98
  9  ω     33.00  98.00   1.00   24.00    --  104.50 -45.00 150.00   65
 10  ω     33.00  98.00   1.00   24.00    --  104.50 -45.00 -90.00   65
 11  ω     30.00  91.00   1.00   24.00    --  104.50 -30.00  90.00   61
 12  ω     23.00 109.00   1.00   24.00    --  104.50 -94.00  60.00   86
 13  ω     30.00  91.00   1.00   24.00    --  104.50 -30.00-180.00   61
 14  ω     30.00  91.00   1.00   24.00    --  104.50 -30.00 -30.00   61
 15  ω     23.00 109.00   1.00   24.00    --  104.50 -94.00  30.00   86
 16  ω     23.00 109.00   1.00   24.00    --  104.50 -94.00 -60.00   86
 17  ω     23.00 109.00   1.00   24.00    --  104.50 -94.00 150.00   86
 18  ω    -94.00  -2.00   1.00    6.00    --  -38.50 125.00  90.00   92
 19  ω     11.00 117.00   1.00    6.00    --   42.83  77.00-120.00  106
 20  ω     16.00 113.00   1.00    6.00    --   42.83  57.00  60.00   97
 21  ω     16.00 113.00   1.00    6.00    --   42.83  57.00-150.00   97
 22  ω     11.00 117.00   1.00    6.00    --   42.83  77.00 -30.00  106
 23  ω     73.00 178.00   1.00   24.00    --  104.50  77.00  30.00  105
 24  ω     81.00 178.00   1.00   24.00    --  104.50  30.00-180.00   97
 25  ω     77.00 102.00   1.00   24.00    --  104.50  61.00-150.00   25
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas S2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1706627000
_diffrn_orient_matrix_UB_12      0.0418094000
_diffrn_orient_matrix_UB_13      0.0041163000
_diffrn_orient_matrix_UB_21      0.0152040000
_diffrn_orient_matrix_UB_22      0.3158298000
_diffrn_orient_matrix_UB_23      -0.0279232000
_diffrn_orient_matrix_UB_31      -0.0228339000
_diffrn_orient_matrix_UB_32      -0.1031227000
_diffrn_orient_matrix_UB_33      -0.0837539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2777
_reflns_number_total             2828
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2828
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.073
_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)+(0.0352P)²+0.1508P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0665
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O22-H22
 0.84 with sigma of 0.02
 O4-H4
 0.84 with sigma of 0.02
 O2-H2
 0.84 with sigma of 0.02
 O8-H8
 0.84 with sigma of 0.02
 O12-H12
 0.84 with sigma of 0.02
3. Restrained planarity
 C13, C14, C15, C19
 with sigma of 0.01
4.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C15(H15)
4.d Fitted hexagon refined as free rotating group:
 C17(C18,C19,C14,C15,C16)
4.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
4.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
C1 C -0.18704(18) 1.1767(4) 0.71057(10) 0.0185(4) Uani 1 1 d . . . . .
H1A H -0.175833 1.028610 0.751602 0.022 Uiso 1 1 calc R . . . .
H1B H -0.149762 1.364202 0.731836 0.022 Uiso 1 1 calc R . . . .
O2 O -0.34221(13) 1.2047(3) 0.68693(7) 0.0199(3) Uani 1 1 d D . . . .
H2 H -0.354700 1.355776 0.660333 0.030 Uiso 1 1 calc DGR . . . .
C3 C -0.09373(18) 1.0891(4) 0.64405(9) 0.0136(3) Uani 1 1 d . . . . .
H3 H -0.137670 0.911995 0.618424 0.016 Uiso 1 1 calc R . . . .
O4 O -0.09796(13) 1.3267(3) 0.59158(7) 0.0154(3) Uani 1 1 d D . . . .
H4 H -0.102(2) 1.263(5) 0.5473(11) 0.023 Uiso 1 1 d DR . . . .
C5 C 0.06953(18) 1.0323(4) 0.67023(10) 0.0136(3) Uani 1 1 d . . . . .
H5 H 0.110961 1.211802 0.695707 0.016 Uiso 1 1 calc R . . . .
O6 O 0.07212(12) 0.8009(2) 0.72596(6) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.16854(18) 0.9525(4) 0.60471(10) 0.0135(3) Uani 1 1 d . . . . .
H7 H 0.178564 1.127853 0.571529 0.016 Uiso 1 1 calc R . . . .
O8 O 0.10706(13) 0.7218(3) 0.55805(7) 0.0169(3) Uani 1 1 d D . . . .
H8 H 0.050(2) 0.612(5) 0.5817(13) 0.025 Uiso 1 1 d DR . . . .
C9 C 0.32462(19) 0.8712(4) 0.63816(10) 0.0148(3) Uani 1 1 d . . . . .
H9 H 0.373612 1.048881 0.660921 0.018 Uiso 1 1 calc R . . . .
O10 O 0.31280(13) 0.6559(3) 0.69751(7) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.42357(18) 0.7476(4) 0.57840(10) 0.0179(3) Uani 1 1 d . . . . .
H11A H 0.382528 0.557778 0.560756 0.021 Uiso 1 1 calc R . . . .
H11B H 0.421767 0.879888 0.533631 0.021 Uiso 1 1 calc R . . . .
O12 O 0.57516(14) 0.7089(3) 0.60666(8) 0.0230(3) Uani 1 1 d D . . . .
H12 H 0.604(3) 0.861(5) 0.6289(14) 0.034 Uiso 1 1 d DR . . . .
C13 C 0.22218(18) 0.7618(4) 0.75548(9) 0.0149(3) Uani 1 1 d . . . . .
H13 H 0.262647 0.953671 0.773742 0.018 Uiso 1 1 calc R . . . .
C17 C 0.25377(13) 0.1740(2) 0.94635(6) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.11740(11) 0.3080(3) 0.92710(6) 0.0203(4) Uani 1 1 d G . . . .
H18 H 0.032710 0.270628 0.956464 0.024 Uiso 1 1 calc R . . . .
C19 C 0.10495(10) 0.4966(3) 0.86490(7) 0.0187(4) Uani 1 1 d G . . . .
H19 H 0.011748 0.588190 0.851752 0.022 Uiso 1 1 calc R . . . .
C14 C 0.22887(12) 0.5512(2) 0.82194(6) 0.0161(3) Uani 1 1 d G . . . .
C15 C 0.36524(10) 0.4172(3) 0.84119(6) 0.0166(3) Uani 1 1 d G . . . .
H15 H 0.449928 0.454579 0.811825 0.020 Uiso 1 1 calc R . . . .
C16 C 0.37769(10) 0.2286(2) 0.90339(6) 0.0167(3) Uani 1 1 d G . . . .
O20 O 0.50731(14) 0.0867(3) 0.92786(7) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.6179(2) 0.0465(4) 0.87180(10) 0.0216(4) Uani 1 1 d . . . . .
H21A H 0.569562 -0.030302 0.824363 0.032 Uiso 1 1 calc GR . . . .
H21B H 0.694355 -0.091085 0.891558 0.032 Uiso 1 1 calc GR . . . .
H21C H 0.665396 0.233329 0.861240 0.032 Uiso 1 1 calc GR . . . .
O22 O 0.26341(15) -0.0163(3) 1.00685(8) 0.0225(3) Uani 1 1 d D . . . .
H22 H 0.346(2) -0.109(6) 1.0051(15) 0.034 Uiso 1 1 d DR . . . .


_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
C1 O2 1.4303(19) . ?
C1 C3 1.517(2) . ?
C3 O4 1.426(2) . ?
C3 C5 1.527(2) . ?
C5 O6 1.4415(19) . ?
C5 C7 1.525(2) . ?
O6 C13 1.4215(19) . ?
C7 O8 1.430(2) . ?
C7 C9 1.529(2) . ?
C9 O10 1.441(2) . ?
C9 C11 1.511(2) . ?
O10 C13 1.413(2) . ?
C11 O12 1.427(2) . ?
C13 C14 1.5102(18) . ?
C17 C18 1.3900 . ?
C17 C16 1.3900 . ?
C17 O22 1.3712(15) . ?
C18 C19 1.3900 . ?
C19 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 O20 1.3770(14) . ?
O20 C21 1.437(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
O2 C1 C3 111.35(13) . . ?
C1 C3 C5 111.64(13) . . ?
O4 C3 C1 106.86(14) . . ?
O4 C3 C5 108.50(13) . . ?
O6 C5 C3 108.11(13) . . ?
O6 C5 C7 109.75(13) . . ?
C7 C5 C3 113.39(13) . . ?
C13 O6 C5 108.70(12) . . ?
C5 C7 C9 108.89(13) . . ?
O8 C7 C5 112.69(13) . . ?
O8 C7 C9 110.58(13) . . ?
O10 C9 C7 110.13(13) . . ?
O10 C9 C11 107.72(14) . . ?
C11 C9 C7 112.40(14) . . ?
C13 O10 C9 110.08(12) . . ?
O12 C11 C9 112.64(14) . . ?
O6 C13 C14 111.06(12) . . ?
O10 C13 O6 110.28(12) . . ?
O10 C13 C14 109.10(12) . . ?
C18 C17 C16 120.0 . . ?
O22 C17 C18 119.29(9) . . ?
O22 C17 C16 120.69(9) . . ?
C17 C18 C19 120.0 . . ?
C18 C19 C14 120.0 . . ?
C19 C14 C13 121.93(9) . . ?
C15 C14 C13 118.04(9) . . ?
C15 C14 C19 120.0 . . ?
C14 C15 C16 120.0 . . ?
C15 C16 C17 120.0 . . ?
O20 C16 C17 115.18(9) . . ?
O20 C16 C15 124.82(9) . . ?
C16 O20 C21 116.43(12) . . ?

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
_geom_hbond_publ_flag
O2 H2 O12 0.84 1.96 2.7898(18) 168.3 1_465 yes
O4 H4 O8 0.825(19) 1.847(19) 2.6531(17) 165(3) 2_556 yes
O8 H8 O4 0.844(19) 1.87(2) 2.6649(17) 156(2) 1_545 yes
O12 H12 O2 0.83(2) 1.93(2) 2.7580(19) 175(3) 1_655 yes

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.782
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
