# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2049548'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2016-06-02
_audit_creation_method           CRYSTALS_ver_14.61_build_5555

_oxford_structure_analysis_title 6588
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   12.1157(4)
_cell_length_b                   6.1134(2)
_cell_length_c                   9.9700(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     738.46(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z+1/2
-x+1/2,y+1/2,z+1/2
x+1/2,-y+1/2,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
D 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C7 H4 D6 O6 
# Dc =      1.76 Fooo =    400.00 Mu =     13.32 M =    196.19
# Found Formula = C7 H4 D6 O6 
# Dc =      1.76 FOOO =    400.00 Mu =     13.32 M =    196.19

_chemical_formula_sum            'C7 H4 D6 O6'
_chemical_formula_moiety         'C7 H4 D6 O6'
_chemical_compound_source        .
_chemical_formula_weight         196.19


_cell_measurement_reflns_used    4581
_cell_measurement_theta_min      4
_cell_measurement_theta_max      77
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.12
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.38

_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    1.332

# Sheldrick geometric approximatio 0.77 0.85 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.85
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            6213
_reflns_number_total             1449
_diffrn_reflns_av_R_equivalents  0.021
# Number of reflections without Friedels Law is 1449 
# Number of reflections with Friedels Law is 826 
# Theoretical number of reflections is about 780 


_diffrn_reflns_theta_min         7.311
_diffrn_reflns_theta_max         76.931
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.931
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              0
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              -11
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   1.79
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.20
_refine_diff_density_max         0.30


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     1
_refine_ls_number_parameters     119
_oxford_refine_ls_R_factor_ref   0.0310
_refine_ls_wR_factor_ref         0.0816
_refine_ls_goodness_of_fit_ref   1.0267
_refine_ls_shift/su_max          0.0003217
_refine_ls_shift/su_mean         0.0000385


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1447
_refine_ls_R_factor_all          0.0310
_refine_ls_wR_factor_all         0.0816

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1442
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_gt          0.0816

_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_abs_structure_details 'Flack (1983), 623 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.16P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.54973(11) -0.0661(2) 0.27724(17) 0.0154 1.0000 Uani . . . . . .
C2 C 0.63892(12) -0.0625(2) 0.38476(16) 0.0165 1.0000 Uani . . . . . .
C3 C 0.74586(11) 0.0391(2) 0.33182(16) 0.0174 1.0000 Uani . . . . . .
C4 C 0.71961(10) 0.2716(2) 0.28719(17) 0.0174 1.0000 Uani . . . . . .
C5 C 0.63080(11) 0.2770(2) 0.17867(16) 0.0170 1.0000 Uani . . . . . .
C6 C 0.52725(11) 0.1707(2) 0.23665(17) 0.0163 1.0000 Uani . . . . . .
O7 O 0.60081(8) 0.07281(16) 0.49499(14) 0.0194 1.0000 Uani . . . . . .
O8 O 0.67612(9) 0.38679(17) 0.40253(15) 0.0216 1.0000 Uani . . . . . .
O9 O 0.49556(8) 0.29107(17) 0.35511(15) 0.0211 1.0000 Uani . . . . . .
C10 C 0.58000(11) 0.2866(2) 0.45103(18) 0.0195 1.0000 Uani . . . . . .
O11 O 0.45233(9) -0.17235(19) 0.32146(15) 0.0250 1.0000 Uani . . . . . .
O12 O 0.78649(9) -0.08101(19) 0.21997(15) 0.0253 1.0000 Uani . . . . . .
O13 O 0.66403(8) 0.17366(18) 0.05697(15) 0.0199 1.0000 Uani . . . . . .
D11 D 0.5781 -0.1486 0.1996 0.0152 1.0000 Uiso R . . . . .
D21 D 0.6524 -0.2121 0.4177 0.0181 1.0000 Uiso R . . . . .
D31 D 0.8009 0.0438 0.4025 0.0208 1.0000 Uiso R . . . . .
D41 D 0.7867 0.3479 0.2583 0.0215 1.0000 Uiso R . . . . .
D51 D 0.6136 0.4324 0.1578 0.0199 1.0000 Uiso R . . . . .
D61 D 0.4656 0.1767 0.1729 0.0185 1.0000 Uiso R . . . . .
H101 H 0.5550 0.3704 0.5284 0.0239 1.0000 Uiso R . . . . .
H111 H 0.4367 -0.1300 0.3984 0.0367 1.0000 Uiso R . . . . .
H121 H 0.8344 -0.1673 0.2458 0.0385 1.0000 Uiso R . . . . .
H131 H 0.7088 0.0741 0.0682 0.0309 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0131(5) 0.0174(6) 0.0157(6) -0.0024(5) 0.0029(5) -0.0046(5)
C2 0.0171(6) 0.0177(6) 0.0146(6) 0.0000(6) 0.0012(5) 0.0011(5)
C3 0.0123(6) 0.0247(7) 0.0152(7) 0.0001(5) -0.0016(5) 0.0038(5)
C4 0.0102(6) 0.0220(7) 0.0202(7) -0.0006(5) 0.0003(5) -0.0033(5)
C5 0.0145(6) 0.0169(6) 0.0197(7) 0.0031(5) 0.0004(5) 0.0004(5)
C6 0.0092(6) 0.0220(7) 0.0177(7) -0.0018(5) -0.0001(5) 0.0009(5)
O7 0.0203(5) 0.0240(5) 0.0140(5) -0.0028(4) 0.0029(4) -0.0031(4)
O8 0.0184(5) 0.0212(5) 0.0253(6) -0.0076(4) 0.0032(4) -0.0069(4)
O9 0.0129(4) 0.0242(5) 0.0261(6) -0.0058(4) 0.0021(4) 0.0048(4)
C10 0.0147(6) 0.0221(7) 0.0217(7) -0.0071(5) 0.0026(6) -0.0023(5)
O11 0.0248(5) 0.0300(5) 0.0203(5) -0.0082(4) 0.0073(4) -0.0164(4)
O12 0.0206(5) 0.0348(6) 0.0205(5) -0.0006(4) 0.0011(4) 0.0159(5)
O13 0.0157(5) 0.0286(5) 0.0154(5) 0.0035(4) 0.0004(4) 0.0020(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          12.5(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.5223(19) yes
C1 . C6 . 1.5273(18) yes
C1 . O11 . 1.4174(16) yes
C1 . D11 . 0.986 yes
C2 . C3 . 1.5309(18) yes
C2 . O7 . 1.4509(16) yes
C2 . D21 . 0.985 yes
C3 . C4 . 1.5229(19) yes
C3 . O12 . 1.4231(17) yes
C3 . D31 . 0.971 yes
C4 . C5 . 1.5263(18) yes
C4 . O8 . 1.4476(17) yes
C4 . D41 . 0.980 yes
C5 . C6 . 1.5265(18) yes
C5 . O13 . 1.4260(18) yes
C5 . D51 . 0.995 yes
C6 . O9 . 1.4435(17) yes
C6 . D61 . 0.981 yes
O7 . C10 . 1.4014(18) yes
O8 . C10 . 1.4018(17) yes
O9 . C10 . 1.4007(19) yes
C10 . H101 . 0.975 no
O11 . H111 . 0.831 no
O12 . H121 . 0.826 no
O13 . H131 . 0.823 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 107.43(11) yes
C2 . C1 . O11 . 112.24(11) yes
C6 . C1 . O11 . 111.62(11) yes
C2 . C1 . D11 . 108.220 yes
C6 . C1 . D11 . 109.836 yes
O11 . C1 . D11 . 107.447 yes
C1 . C2 . C3 . 111.34(11) yes
C1 . C2 . O7 . 108.40(11) yes
C3 . C2 . O7 . 107.40(10) yes
C1 . C2 . D21 . 109.814 yes
C3 . C2 . D21 . 110.576 yes
O7 . C2 . D21 . 109.234 yes
C2 . C3 . C4 . 107.62(10) yes
C2 . C3 . O12 . 110.69(11) yes
C4 . C3 . O12 . 108.97(11) yes
C2 . C3 . D31 . 110.073 yes
C4 . C3 . D31 . 109.178 yes
O12 . C3 . D31 . 110.242 yes
C3 . C4 . C5 . 111.98(11) yes
C3 . C4 . O8 . 107.33(11) yes
C5 . C4 . O8 . 107.23(11) yes
C3 . C4 . D41 . 110.894 yes
C5 . C4 . D41 . 111.493 yes
O8 . C4 . D41 . 107.669 yes
C4 . C5 . C6 . 107.57(11) yes
C4 . C5 . O13 . 113.25(11) yes
C6 . C5 . O13 . 111.46(11) yes
C4 . C5 . D51 . 108.440 yes
C6 . C5 . D51 . 108.312 yes
O13 . C5 . D51 . 107.676 yes
C1 . C6 . C5 . 110.92(11) yes
C1 . C6 . O9 . 108.29(11) yes
C5 . C6 . O9 . 108.14(11) yes
C1 . C6 . D61 . 110.031 yes
C5 . C6 . D61 . 111.362 yes
O9 . C6 . D61 . 107.975 yes
C2 . O7 . C10 . 110.61(11) yes
C4 . O8 . C10 . 111.34(10) yes
C6 . O9 . C10 . 110.76(10) yes
O8 . C10 . O7 . 111.47(11) yes
O8 . C10 . O9 . 111.27(13) yes
O7 . C10 . O9 . 111.29(11) yes
O8 . C10 . H101 . 107.6 no
O7 . C10 . H101 . 107.4 no
O9 . C10 . H101 . 107.6 no
C1 . O11 . H111 . 109.5 no
C3 . O12 . H121 . 109.2 no
C5 . O13 . H131 . 113.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O11 . H111 . O13 2_655 145 0.83 2.01 2.739(2) yes
O12 . H121 . O11 4_545 171 0.83 1.89 2.708(2) yes
O13 . H131 . O8 3_644 129 0.82 2.45 3.033(2) yes
O13 . H131 . O12 . 139 0.82 2.02 2.696(2) yes


_iucr_refine_instructions_details 
;
#
# Punched on 02/06/16 at 08:53:12
#
#LIST     12                                                                    
BLOCK SCALE X'S  U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) D   (  11,X'S) 
RIDE C   (   2,X'S) D   (  21,X'S) 
RIDE C   (   3,X'S) D   (  31,X'S) 
RIDE C   (   4,X'S) D   (  41,X'S) 
RIDE C   (   5,X'S) D   (  51,X'S) 
RIDE C   (   6,X'S) D   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE O   (  11,X'S) H   ( 111,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE O   (  13,X'S) H   ( 131,X'S) 
END                                                                             
#
# Punched on 02/06/16 at 08:53:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 1 0 x .
4 0 2 x .
####################################################################### 
# 
# 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_26
_database_code_depnum_ccdc_archive 'CCDC 2049549'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2020-12-28 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2016-09-14
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 6617
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.4164(2)
_cell_length_b                   6.6513(2)
_cell_length_c                   11.2592(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.9535(17)
_cell_angle_gamma                90
_cell_volume                     774.33(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21 '
_symmetry_space_group_name_Hall  'P 2yb'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C14 H18 O8 
# Dc =      1.35 Fooo =    332.00 Mu =      9.56 M =    314.29
# Found Formula = C14 H18 O8 
# Dc =      1.35 FOOO =    332.00 Mu =      9.56 M =    314.29

_chemical_formula_sum            'C14 H18 O8'
_chemical_formula_moiety         'C14 H18 O8'
_chemical_compound_source        .
_chemical_formula_weight         314.29


_cell_measurement_reflns_used    5870
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.23

_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.956

# Sheldrick geometric approximatio 0.86 0.87 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.87
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            8925
_reflns_number_total             3187
_diffrn_reflns_av_R_equivalents  0.017
_diffrn_reflns_av_sigmaI/netI    0.0232
# Number of reflections without Friedels Law is 3187 
# Number of reflections with Friedels Law is 1754 
# Theoretical number of reflections is about 1171 


_diffrn_reflns_theta_min         3.955
_diffrn_reflns_theta_max         76.044
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.523
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -13
_reflns_limit_h_max              13
_reflns_limit_k_min              -8
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.32
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.10
_refine_diff_density_max         0.10


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     1
_refine_ls_number_parameters     200
_oxford_refine_ls_R_factor_ref   0.0230
_refine_ls_wR_factor_ref         0.0591
_refine_ls_goodness_of_fit_ref   1.0108
_refine_ls_shift/su_max          0.0002838
_refine_ls_shift/su_mean         0.0000339


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2322
_refine_ls_R_factor_all          0.0230
_refine_ls_wR_factor_all         0.0591

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2298
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_gt          0.0590

_refine_ls_abs_structure_Flack   0.24(13)
_refine_ls_abs_structure_details 'Flack (1983), 1433 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.07P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.39526(14) 0.0227(2) 0.86145(12) 0.0333 1.0000 Uani . . . . . .
C2 C 0.52036(14) -0.0160(2) 0.88426(11) 0.0321 1.0000 Uani . . . . . .
C3 C 0.62332(12) 0.1169(2) 0.84572(11) 0.0285 1.0000 Uani . . . . . .
C4 C 0.56941(13) 0.3214(2) 0.80513(11) 0.0269 1.0000 Uani . . . . . .
C5 C 0.44215(13) 0.2988(2) 0.72435(11) 0.0272 1.0000 Uani . . . . . .
C6 C 0.34086(12) 0.2026(2) 0.79295(11) 0.0301 1.0000 Uani . . . . . .
O7 O 0.71939(8) 0.14430(17) 0.94933(7) 0.0315 1.0000 Uani . . . . . .
C8 C 0.84522(13) 0.1528(2) 0.93112(13) 0.0349 1.0000 Uani . . . . . .
O9 O 0.88208(9) 0.1324(2) 0.83494(9) 0.0451 1.0000 Uani . . . . . .
C10 C 0.92852(15) 0.1950(3) 1.04556(14) 0.0478 1.0000 Uani . . . . . .
O11 O 0.65745(9) 0.42096(16) 0.73499(7) 0.0291 1.0000 Uani . . . . . .
C12 C 0.73459(12) 0.5670(2) 0.78791(11) 0.0286 1.0000 Uani . . . . . .
O13 O 0.73408(9) 0.61743(18) 0.89031(8) 0.0381 1.0000 Uani . . . . . .
C14 C 0.82002(13) 0.6503(2) 0.70279(12) 0.0352 1.0000 Uani . . . . . .
O15 O 0.40116(9) 0.49775(15) 0.68807(8) 0.0305 1.0000 Uani . . . . . .
C16 C 0.36952(13) 0.5359(2) 0.57067(12) 0.0320 1.0000 Uani . . . . . .
O17 O 0.37665(13) 0.4129(2) 0.49407(9) 0.0569 1.0000 Uani . . . . . .
C18 C 0.32664(17) 0.7465(2) 0.55214(14) 0.0433 1.0000 Uani . . . . . .
O19 O 0.23392(8) 0.12757(16) 0.70981(8) 0.0331 1.0000 Uani . . . . . .
C20 C 0.12981(13) 0.2466(2) 0.68014(12) 0.0345 1.0000 Uani . . . . . .
O21 O 0.12225(10) 0.41625(19) 0.71361(11) 0.0500 1.0000 Uani . . . . . .
C22 C 0.02857(13) 0.1377(3) 0.59962(13) 0.0422 1.0000 Uani . . . . . .
H11 H 0.3355 -0.0631 0.8889 0.0399 1.0000 Uiso R . . . . .
H21 H 0.5483 -0.1367 0.9257 0.0388 1.0000 Uiso R . . . . .
H31 H 0.6602 0.0597 0.7811 0.0337 1.0000 Uiso R . . . . .
H41 H 0.5583 0.4045 0.8719 0.0284 1.0000 Uiso R . . . . .
H51 H 0.4532 0.2169 0.6548 0.0301 1.0000 Uiso R . . . . .
H61 H 0.3083 0.3007 0.8443 0.0328 1.0000 Uiso R . . . . .
H101 H 1.0168 0.1889 1.0358 0.0703 1.0000 Uiso R . . . . .
H102 H 0.9086 0.1009 1.1035 0.0728 1.0000 Uiso R . . . . .
H103 H 0.9094 0.3263 1.0743 0.0725 1.0000 Uiso R . . . . .
H141 H 0.8527 0.7798 0.7323 0.0529 1.0000 Uiso R . . . . .
H142 H 0.8911 0.5582 0.7050 0.0532 1.0000 Uiso R . . . . .
H143 H 0.7737 0.6568 0.6236 0.0526 1.0000 Uiso R . . . . .
H181 H 0.2989 0.7703 0.4677 0.0622 1.0000 Uiso R . . . . .
H182 H 0.3995 0.8294 0.5766 0.0658 1.0000 Uiso R . . . . .
H183 H 0.2562 0.7723 0.5996 0.0639 1.0000 Uiso R . . . . .
H221 H -0.0532 0.1790 0.6196 0.0656 1.0000 Uiso R . . . . .
H222 H 0.0405 0.0006 0.6126 0.0660 1.0000 Uiso R . . . . .
H223 H 0.0364 0.1743 0.5202 0.0657 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0313(7) 0.0371(8) 0.0321(6) 0.0037(6) 0.0064(5) -0.0047(6)
C2 0.0362(8) 0.0317(7) 0.0289(6) 0.0036(5) 0.0055(5) -0.0001(6)
C3 0.0277(6) 0.0334(7) 0.0245(5) -0.0012(6) 0.0035(5) 0.0025(6)
C4 0.0278(7) 0.0297(6) 0.0241(6) -0.0014(5) 0.0064(5) -0.0020(5)
C5 0.0291(7) 0.0262(6) 0.0259(6) -0.0019(5) 0.0024(5) 0.0025(5)
C6 0.0251(6) 0.0349(7) 0.0300(6) -0.0045(6) 0.0022(5) 0.0002(5)
O7 0.0264(4) 0.0401(5) 0.0275(4) 0.0013(4) 0.0010(3) 0.0038(4)
C8 0.0294(7) 0.0332(7) 0.0419(8) 0.0064(6) 0.0041(6) 0.0023(6)
O9 0.0320(5) 0.0611(7) 0.0438(5) 0.0014(5) 0.0114(4) 0.0001(5)
C10 0.0328(8) 0.0603(11) 0.0475(8) 0.0049(7) -0.0060(6) -0.0021(7)
O11 0.0310(5) 0.0317(5) 0.0253(4) -0.0010(4) 0.0063(3) -0.0037(4)
C12 0.0236(6) 0.0280(6) 0.0334(7) 0.0004(5) 0.0004(5) 0.0041(5)
O13 0.0346(5) 0.0450(6) 0.0350(5) -0.0097(5) 0.0047(4) -0.0092(5)
C14 0.0305(7) 0.0355(7) 0.0398(7) 0.0029(6) 0.0049(5) -0.0005(6)
O15 0.0359(5) 0.0285(5) 0.0266(4) 0.0003(4) 0.0023(4) 0.0039(4)
C16 0.0276(7) 0.0381(8) 0.0290(6) -0.0007(6) -0.0025(5) 0.0001(6)
O17 0.0826(9) 0.0512(7) 0.0315(5) -0.0085(5) -0.0144(5) 0.0155(7)
C18 0.0470(9) 0.0428(8) 0.0391(8) 0.0082(7) 0.0012(6) 0.0052(7)
O19 0.0254(4) 0.0347(5) 0.0383(5) -0.0045(4) 0.0009(3) 0.0004(4)
C20 0.0269(7) 0.0415(8) 0.0358(7) 0.0003(6) 0.0062(5) 0.0017(6)
O21 0.0348(6) 0.0459(7) 0.0674(7) -0.0108(6) -0.0017(5) 0.0091(5)
C22 0.0314(7) 0.0553(9) 0.0392(7) -0.0036(8) 0.0013(5) -0.0011(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          11.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.323(2) yes
C1 . C6 . 1.497(2) yes
C1 . H11 . 0.925 no
C2 . C3 . 1.4940(19) yes
C2 . H21 . 0.956 no
C3 . C4 . 1.5207(19) yes
C3 . O7 . 1.4536(15) yes
C3 . H31 . 0.943 no
C4 . C5 . 1.5215(18) yes
C4 . O11 . 1.4419(15) yes
C4 . H41 . 0.952 no
C5 . C6 . 1.5222(18) yes
C5 . O15 . 1.4343(17) yes
C5 . H51 . 0.973 no
C6 . O19 . 1.4538(16) yes
C6 . H61 . 0.960 no
O7 . C8 . 1.3521(16) yes
C8 . O9 . 1.1996(17) yes
C8 . C10 . 1.490(2) yes
C10 . H101 . 0.940 no
C10 . H102 . 0.945 no
C10 . H103 . 0.961 no
O11 . C12 . 1.3520(16) yes
C12 . O13 . 1.2014(16) yes
C12 . C14 . 1.4914(19) yes
C14 . H141 . 0.970 no
C14 . H142 . 0.959 no
C14 . H143 . 0.962 no
O15 . C16 . 1.3470(17) yes
C16 . O17 . 1.1972(18) yes
C16 . C18 . 1.478(2) yes
C18 . H181 . 0.972 no
C18 . H182 . 0.951 no
C18 . H183 . 0.974 no
O19 . C20 . 1.3516(18) yes
C20 . O21 . 1.195(2) yes
C20 . C22 . 1.492(2) yes
C22 . H221 . 0.947 no
C22 . H222 . 0.930 no
C22 . H223 . 0.940 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 123.91(13) yes
C2 . C1 . H11 . 120.2 no
C6 . C1 . H11 . 115.9 no
C1 . C2 . C3 . 123.62(13) yes
C1 . C2 . H21 . 119.5 no
C3 . C2 . H21 . 116.8 no
C2 . C3 . C4 . 111.37(11) yes
C2 . C3 . O7 . 106.85(10) yes
C4 . C3 . O7 . 108.80(11) yes
C2 . C3 . H31 . 111.1 no
C4 . C3 . H31 . 107.4 no
O7 . C3 . H31 . 111.4 no
C3 . C4 . C5 . 110.78(10) yes
C3 . C4 . O11 . 109.83(10) yes
C5 . C4 . O11 . 106.48(10) yes
C3 . C4 . H41 . 111.0 no
C5 . C4 . H41 . 110.4 no
O11 . C4 . H41 . 108.2 no
C4 . C5 . C6 . 110.21(10) yes
C4 . C5 . O15 . 106.69(10) yes
C6 . C5 . O15 . 109.38(10) yes
C4 . C5 . H51 . 110.9 no
C6 . C5 . H51 . 109.3 no
O15 . C5 . H51 . 110.3 no
C5 . C6 . C1 . 110.81(11) yes
C5 . C6 . O19 . 109.98(10) yes
C1 . C6 . O19 . 105.67(11) yes
C5 . C6 . H61 . 109.7 no
C1 . C6 . H61 . 111.8 no
O19 . C6 . H61 . 108.8 no
C3 . O7 . C8 . 117.99(10) yes
O7 . C8 . O9 . 123.66(13) yes
O7 . C8 . C10 . 110.51(12) yes
O9 . C8 . C10 . 125.82(13) yes
C8 . C10 . H101 . 111.5 no
C8 . C10 . H102 . 108.5 no
H101 . C10 . H102 . 110.6 no
C8 . C10 . H103 . 109.9 no
H101 . C10 . H103 . 108.9 no
H102 . C10 . H103 . 107.4 no
C4 . O11 . C12 . 118.17(9) yes
O11 . C12 . O13 . 123.52(12) yes
O11 . C12 . C14 . 110.66(11) yes
O13 . C12 . C14 . 125.81(12) yes
C12 . C14 . H141 . 108.8 no
C12 . C14 . H142 . 105.4 no
H141 . C14 . H142 . 108.7 no
C12 . C14 . H143 . 109.9 no
H141 . C14 . H143 . 113.1 no
H142 . C14 . H143 . 110.6 no
C5 . O15 . C16 . 118.82(10) yes
O15 . C16 . O17 . 123.32(13) yes
O15 . C16 . C18 . 110.54(12) yes
O17 . C16 . C18 . 126.14(14) yes
C16 . C18 . H181 . 110.0 no
C16 . C18 . H182 . 106.9 no
H181 . C18 . H182 . 108.7 no
C16 . C18 . H183 . 108.9 no
H181 . C18 . H183 . 110.7 no
H182 . C18 . H183 . 111.5 no
C6 . O19 . C20 . 119.17(11) yes
O19 . C20 . O21 . 123.82(13) yes
O19 . C20 . C22 . 110.65(13) yes
O21 . C20 . C22 . 125.53(14) yes
C20 . C22 . H221 . 107.7 no
C20 . C22 . H222 . 108.0 no
H221 . C22 . H222 . 110.7 no
C20 . C22 . H223 . 108.4 no
H221 . C22 . H223 . 109.6 no
H222 . C22 . H223 . 112.2 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C10 . H102 . O21 2_647 166.75 0.945 2.452 3.379(2) yes
C14 . H142 . O21 1_655 161.77 0.959 2.577 3.501(2) yes
C14 . H143 . O17 2_656 135.52 0.962 2.571 3.326(2) yes
C18 . H181 . O11 2_656 149.77 0.972 2.582 3.458(2) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 15/09/16 at 13:19:57
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 102,X'S) H   ( 103,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 15/09/16 at 13:19:57
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 -1 2 x .
-1 1 2 x .
