# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1536896'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-06-23 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
? 
;
#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.67257(5)
_cell_length_b                   13.30378(6)
_cell_length_c                   15.10494(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1541.825(7)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2

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            4

# Given Formula = C16 H20 O6 
# Dc =      1.33 Fooo =    656.00 Mu =      8.50 M =    308.33
# Found Formula = C16 H20 O6 
# Dc =      1.33 FOOO =    656.00 Mu =      8.50 M =    308.33

_chemical_formula_sum            'C16 H20 O6'
_chemical_formula_moiety         'C16 H20 O6'
_chemical_compound_source        ?
_chemical_formula_weight         308.33


_cell_measurement_reflns_used    58203
_cell_measurement_theta_min      4.4110
_cell_measurement_theta_max      61.0530
_cell_measurement_temperature    100

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.850

# Sheldrick geometric approximatio 0.96 0.96 
# No experimental values of Tmin/max available 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.39734
_exptl_absorpt_correction_T_max  1.00000
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# 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      100
_diffrn_reflns_number            90481
_reflns_number_total             2379
_diffrn_reflns_av_R_equivalents  0.063
# Number of reflections without Friedels Law is 2379 
# Number of reflections with Friedels Law is 1393 
# Theoretical number of reflections is about 1188 


_diffrn_reflns_theta_min         3.3220
_diffrn_reflns_theta_max         61.258
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        61.258
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.52
_oxford_diffrn_Wilson_scale      0.04

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

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.13


# 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         2368
_refine_ls_number_restraints     2
_refine_ls_number_parameters     207
_oxford_refine_ls_R_factor_ref   0.0228
_refine_ls_wR_factor_ref         0.0553
_refine_ls_goodness_of_fit_ref   0.9905
_refine_ls_shift/su_max          0.0004147
_refine_ls_shift/su_mean         0.0000823


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2368
_refine_ls_R_factor_all          0.0228
_refine_ls_wR_factor_all         0.0553

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2345
_refine_ls_R_factor_gt           0.0226
_refine_ls_wR_factor_gt          0.0551

_refine_ls_abs_structure_Flack   -0.05(14)
_refine_ls_abs_structure_details 'Flack (1983), 986 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    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.48P] 
 ,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
O1 O 0.56911(13) 0.45761(8) 0.87120(6) 0.0247 1.0000 Uani . . . . . .
C2 C 0.45324(19) 0.47311(10) 0.80113(9) 0.0201 1.0000 Uani . . . . . .
O3 O 0.29988(13) 0.46693(8) 0.81246(7) 0.0260 1.0000 Uani . . . . . .
C4 C 0.55625(19) 0.50016(9) 0.72123(9) 0.0174 1.0000 Uani . . . . . .
C5 C 0.72319(18) 0.50879(9) 0.74550(9) 0.0169 1.0000 Uani . . . . . .
C6 C 0.73582(19) 0.47896(10) 0.84051(10) 0.0221 1.0000 Uani . . . . . .
O7 O 0.85984(14) 0.47168(8) 0.88762(7) 0.0300 1.0000 Uani . . . . . .
C8 C 0.88027(17) 0.54435(10) 0.69529(9) 0.0184 1.0000 Uani . . . . . .
C9 C 0.92453(17) 0.65449(10) 0.71540(8) 0.0159 1.0000 Uani . . . . . .
C10 C 0.86628(18) 0.73517(10) 0.65167(8) 0.0168 1.0000 Uani . . . . . .
O11 O 0.99401(13) 0.73658(8) 0.58135(6) 0.0245 1.0000 Uani D . . . . .
C12 C 0.68592(18) 0.72291(10) 0.60965(9) 0.0167 1.0000 Uani . . . . . .
C13 C 0.53792(18) 0.70491(10) 0.67407(9) 0.0167 1.0000 Uani . . . . . .
O14 O 0.53297(13) 0.74664(7) 0.74550(6) 0.0247 1.0000 Uani . . . . . .
C15 C 0.39498(17) 0.63273(10) 0.64484(9) 0.0174 1.0000 Uani . . . . . .
C16 C 0.47155(17) 0.52606(10) 0.63431(9) 0.0180 1.0000 Uani . . . . . .
C17 C 0.33924(19) 0.44727(11) 0.60195(9) 0.0221 1.0000 Uani . . . . . .
C18 C 0.43222(19) 0.35530(10) 0.56365(9) 0.0213 1.0000 Uani . . . . . .
C19 C 0.3094(2) 0.26775(12) 0.54641(11) 0.0319 1.0000 Uani . . . . . .
O20 O 0.32719(13) 0.66666(8) 0.56223(6) 0.0216 1.0000 Uani D . . . . .
C21 C 1.02482(18) 0.67566(10) 0.78518(8) 0.0180 1.0000 Uani . . . . . .
C22 C 1.09379(19) 0.77692(11) 0.81085(9) 0.0238 1.0000 Uani . . . . . .
H81 H 0.9809 0.5022 0.7132 0.0249 1.0000 Uiso R . . . . .
H82 H 0.8597 0.5372 0.6308 0.0241 1.0000 Uiso R . . . . .
H101 H 0.8700 0.8025 0.6840 0.0228 1.0000 Uiso R . . . . .
H122 H 0.6544 0.7886 0.5806 0.0198 1.0000 Uiso R . . . . .
H121 H 0.6873 0.6657 0.5642 0.0206 1.0000 Uiso R . . . . .
H151 H 0.2990 0.6314 0.6907 0.0219 1.0000 Uiso R . . . . .
H161 H 0.5676 0.5314 0.5877 0.0219 1.0000 Uiso R . . . . .
H171 H 0.2628 0.4268 0.6525 0.0274 1.0000 Uiso R . . . . .
H172 H 0.2638 0.4767 0.5552 0.0297 1.0000 Uiso R . . . . .
H182 H 0.5257 0.3347 0.6067 0.0292 1.0000 Uiso R . . . . .
H181 H 0.4930 0.3768 0.5067 0.0287 1.0000 Uiso R . . . . .
H192 H 0.3688 0.2074 0.5230 0.0520 1.0000 Uiso R . . . . .
H191 H 0.2500 0.2469 0.6028 0.0534 1.0000 Uiso R . . . . .
H193 H 0.2183 0.2910 0.5043 0.0521 1.0000 Uiso R . . . . .
H211 H 1.0626 0.6198 0.8224 0.0230 1.0000 Uiso R . . . . .
H223 H 1.2222 0.7733 0.8150 0.0372 1.0000 Uiso R . . . . .
H222 H 1.0483 0.8003 0.8684 0.0379 1.0000 Uiso R . . . . .
H221 H 1.0659 0.8255 0.7636 0.0369 1.0000 Uiso R . . . . .
H111 H 0.948(2) 0.7704(13) 0.5395(10) 0.0396 1.0000 Uiso D . . . . .
H201 H 0.228(2) 0.6927(12) 0.5697(12) 0.0343 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       27(4)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          4.93(7)
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
O1 . C2 . 1.3975(17) yes
O1 . C6 . 1.3898(18) yes
C2 . O3 . 1.1919(17) yes
C2 . C4 . 1.4868(19) yes
C4 . C5 . 1.337(2) yes
C4 . C16 . 1.5050(18) yes
C5 . C6 . 1.492(2) yes
C5 . C8 . 1.500(2) yes
C6 . O7 . 1.1921(18) yes
C8 . C9 . 1.5345(19) yes
C8 . H81 . 0.992 no
C8 . H82 . 0.992 no
C9 . C10 . 1.5095(19) yes
C9 . C21 . 1.3351(19) yes
C10 . O11 . 1.4453(16) yes
C10 . C12 . 1.5311(19) yes
C10 . H101 . 1.020 no
O11 . H111 . 0.852(14) no
C12 . C13 . 1.5145(19) yes
C12 . H122 . 1.007 no
C12 . H121 . 1.025 no
C13 . O14 . 1.2142(16) yes
C13 . C15 . 1.523(2) yes
C15 . C16 . 1.5441(19) yes
C15 . O20 . 1.4253(16) yes
C15 . H151 . 1.011 no
C16 . C17 . 1.5389(19) yes
C16 . H161 . 1.022 no
C17 . C18 . 1.530(2) yes
C17 . H171 . 1.000 no
C17 . H172 . 0.993 no
C18 . C19 . 1.521(2) yes
C18 . H182 . 1.006 no
C18 . H181 . 1.019 no
C19 . H192 . 0.989 no
C19 . H191 . 1.004 no
C19 . H193 . 0.994 no
O20 . H201 . 0.842(14) no
C21 . C22 . 1.498(2) yes
C21 . H211 . 0.975 no
C22 . H223 . 0.989 no
C22 . H222 . 0.987 no
C22 . H221 . 0.986 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 . O1 . C6 . 107.62(10) yes
O1 . C2 . O3 . 120.60(13) yes
O1 . C2 . C4 . 108.20(11) yes
O3 . C2 . C4 . 131.15(13) yes
C2 . C4 . C5 . 107.91(12) yes
C2 . C4 . C16 . 122.28(12) yes
C5 . C4 . C16 . 129.28(13) yes
C4 . C5 . C6 . 107.64(12) yes
C4 . C5 . C8 . 131.14(13) yes
C6 . C5 . C8 . 121.19(12) yes
C5 . C6 . O1 . 108.38(12) yes
C5 . C6 . O7 . 130.35(14) yes
O1 . C6 . O7 . 121.26(13) yes
C5 . C8 . C9 . 112.26(11) yes
C5 . C8 . H81 . 108.0 no
C9 . C8 . H81 . 108.2 no
C5 . C8 . H82 . 109.8 no
C9 . C8 . H82 . 108.8 no
H81 . C8 . H82 . 109.8 no
C8 . C9 . C10 . 119.15(11) yes
C8 . C9 . C21 . 119.03(12) yes
C10 . C9 . C21 . 121.61(12) yes
C9 . C10 . O11 . 106.09(11) yes
C9 . C10 . C12 . 117.15(11) yes
O11 . C10 . C12 . 108.03(10) yes
C9 . C10 . H101 . 108.1 no
O11 . C10 . H101 . 108.7 no
C12 . C10 . H101 . 108.5 no
C10 . O11 . H111 . 105.8(13) no
C10 . C12 . C13 . 115.35(11) yes
C10 . C12 . H122 . 107.8 no
C13 . C12 . H122 . 103.7 no
C10 . C12 . H121 . 110.3 no
C13 . C12 . H121 . 108.7 no
H122 . C12 . H121 . 110.8 no
C12 . C13 . O14 . 121.48(13) yes
C12 . C13 . C15 . 116.96(11) yes
O14 . C13 . C15 . 121.56(12) yes
C13 . C15 . C16 . 109.59(10) yes
C13 . C15 . O20 . 108.47(11) yes
C16 . C15 . O20 . 109.86(11) yes
C13 . C15 . H151 . 109.7 no
C16 . C15 . H151 . 109.3 no
O20 . C15 . H151 . 109.8 no
C15 . C16 . C4 . 106.55(11) yes
C15 . C16 . C17 . 114.07(11) yes
C4 . C16 . C17 . 113.95(12) yes
C15 . C16 . H161 . 106.4 no
C4 . C16 . H161 . 107.8 no
C17 . C16 . H161 . 107.7 no
C16 . C17 . C18 . 110.93(12) yes
C16 . C17 . H171 . 109.3 no
C18 . C17 . H171 . 110.2 no
C16 . C17 . H172 . 110.0 no
C18 . C17 . H172 . 108.6 no
H171 . C17 . H172 . 107.9 no
C17 . C18 . C19 . 112.85(12) yes
C17 . C18 . H182 . 107.8 no
C19 . C18 . H182 . 110.1 no
C17 . C18 . H181 . 107.9 no
C19 . C18 . H181 . 110.7 no
H182 . C18 . H181 . 107.2 no
C18 . C19 . H192 . 113.4 no
C18 . C19 . H191 . 110.3 no
H192 . C19 . H191 . 106.8 no
C18 . C19 . H193 . 107.9 no
H192 . C19 . H193 . 110.4 no
H191 . C19 . H193 . 108.0 no
C15 . O20 . H201 . 110.0(13) no
C9 . C21 . C22 . 126.69(13) yes
C9 . C21 . H211 . 117.8 no
C22 . C21 . H211 . 115.5 no
C21 . C22 . H223 . 109.0 no
C21 . C22 . H222 . 112.7 no
H223 . C22 . H222 . 108.2 no
C21 . C22 . H221 . 109.0 no
H223 . C22 . H221 . 107.1 no
H222 . C22 . H221 . 110.7 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 . H101 . O3 4_656 139 1.02 2.55 3.3802(19) yes
C17 . H171 . O3 . 128 1.00 2.49 3.2048(19) yes
C18 . H182 . O14 4_646 124 1.01 2.56 3.2359(19) yes
O11 . H111 . O20 3_566 172.8(18) 0.852(16) 1.981(16) 2.8281(19) yes
O20 . H201 . O11 1_455 173.1(17) 0.842(16) 1.896(15) 2.7357(19) yes


_chemical_name_systematic        Cornexistin
