# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2005091'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-07-05
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 6993
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_diffrn_special_details          
;
The crystals were very thin plates.
;

_refine_special_details          
; 
Flack Parameter & su  0.032  0.192  @ 

 Using counting statistics weights
       Hooft Parameter & su -0.110  0.096  $ 
           Hole-in-one & su  0.019  0.086    
    Bijvoet Difference & su -0.065  0.091  ?  
(Using  1273 reflections. Correl Coef =  13%)

 Histogram re-weighted,  1086 reflections,  17.8% 
within interval x= -.5 to 1.5
    Bijvoet Difference & su  0.031  0.114    
 Average of Ratios (x) & su  0.031  0.086  & 
 Average of Ratios (x) & su  0.031  0.092  %  
(corrected for npp, * 1.07)

@  Flack,1983, Acta Cryst A39, 876-881
?  Thompson & Watkin, 2011, J Appl Cryst, 44, 1077-1022
$  Hooft et al, 2008, J Appl Cryst, 41, 96-103
&  Cooper et al, to be published

 Hooft probability analysis
 For an enantiopure material, there are 2 choices, P2
 P2(correct)     1.0000   i.e. 0.100000E+01                                     

 If 50:50 twinning is possible, there are 3 choices, P3
 P3(correct)     1.0000   i.e. 0.100000E+01                                     
 P3(rac-twin)    0.0000   i.e. 0.336319E-08                                     
 P3(inverse)     0.0000   i.e. 0.196786E-28                                     
 G              1.2204                                                          
 G S.U.         0.1922 
;

_cell_length_a                   5.8853(2)
_cell_length_b                   7.6219(2)
_cell_length_c                   16.1377(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.424(3)
_cell_angle_gamma                90
_cell_volume                     717.82(4)

_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 = C15 H22 O4 
# Dc =      1.23 Fooo =    288.00 Mu =      7.19 M =    266.34
# Found Formula = C15 H22.00 O4 
# Dc =      1.23 FOOO =    288.00 Mu =      7.19 M =    266.34

_chemical_formula_sum            'C15 H22 O4'
_chemical_formula_moiety         'C15 H22 O4'
_chemical_compound_source        .
_chemical_formula_weight         266.34


_cell_measurement_reflns_used    6370
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.01
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.31

_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             287.998
_exptl_absorpt_coefficient_mu    0.719

# Sheldrick geometric approximatio 0.87 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            11890
_reflns_number_total             2974
_diffrn_reflns_av_R_equivalents  0.051
# Number of reflections without Friedels Law is 2974 
# Number of reflections with Friedels Law is 1623 
# Theoretical number of reflections is about 1502 


_diffrn_reflns_theta_min         5.529
_diffrn_reflns_theta_max         76.168
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.645
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.60
_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         -0.17
_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 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     1
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2971
_oxford_refine_ls_R_factor_ref   0.0458
_refine_ls_R_factor_all          0.0458
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_all         0.1175
_refine_ls_goodness_of_fit_ref   1.0016
_refine_ls_shift/su_max          0.0001425
_refine_ls_shift/su_mean         0.0000267


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        2971
_oxford_refine_ls_R_factor_all   0.0458
_oxford_refine_ls_wR_factor_all  0.1175

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2828
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_gt          0.1151

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.02(9) # for 1143 Friedel pairs 
_oxford_Bijvoet_difference       0.06(9) # for 1143 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.03(19) # for 1351 Friedel pairs 
_refine_ls_abs_structure_Flack   0.06(9)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1143 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) + ( 0.08P)² + 0.14P] 
 ,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 1.4568(5) 0.5000(4) 0.61930(17) 0.0517 1.0000 Uani . . . . . .
C2 C 1.3606(4) 0.4243(3) 0.56100(15) 0.0446 1.0000 Uani . . . . . .
C3 C 1.2320(4) 0.3314(3) 0.49308(15) 0.0444 1.0000 Uani . . . . . .
C4 C 1.1568(4) 0.4022(3) 0.42055(14) 0.0392 1.0000 Uani . . . . . .
C5 C 1.0159(4) 0.3069(3) 0.35017(13) 0.0373 1.0000 Uani . . . . . .
C6 C 0.7894(3) 0.4006(3) 0.32282(11) 0.0316 1.0000 Uani . . . . . .
C7 C 0.8042(3) 0.5879(3) 0.29035(11) 0.0275 1.0000 Uani . . . . . .
C8 C 0.5654(3) 0.6086(3) 0.24291(11) 0.0281 1.0000 Uani . . . . . .
C9 C 0.5201(3) 0.4279(3) 0.20287(11) 0.0293 1.0000 Uani . . . . . .
C10 C 0.5613(3) 0.4063(3) 0.11146(11) 0.0276 1.0000 Uani . . . . . .
C11 C 0.7854(3) 0.4719(2) 0.08303(11) 0.0267 1.0000 Uani . . . . . .
C12 C 0.8390(3) 0.6687(2) 0.09130(11) 0.0256 1.0000 Uani . . . . . .
C13 C 0.9924(3) 0.7133(2) 0.17469(12) 0.0260 1.0000 Uani . . . . . .
C14 C 0.9745(3) 0.9018(3) 0.20520(12) 0.0314 1.0000 Uani . . . . . .
C15 C 1.0700(4) 1.0320(3) 0.14722(15) 0.0414 1.0000 Uani . . . . . .
O16 O 0.3682(2) 0.4820(2) 0.05851(8) 0.0306 1.0000 Uani . . . . . .
O17 O 0.6295(2) 0.77021(18) 0.07671(9) 0.0289 1.0000 Uani . . . . . .
O21 O 0.6677(3) 0.3067(2) 0.25299(8) 0.0349 1.0000 Uani . . . . . .
O22 O 0.9829(2) 0.58430(19) 0.23852(8) 0.0274 1.0000 Uani . . . . . .
H31 H 1.1987 0.2092 0.5017 0.0528 1.0000 Uiso R . . . . .
H41 H 1.1945 0.5212 0.4114 0.0471 1.0000 Uiso R . . . . .
H51 H 0.9862 0.1876 0.3666 0.0450 1.0000 Uiso R . . . . .
H52 H 1.1017 0.3053 0.3019 0.0457 1.0000 Uiso R . . . . .
H61 H 0.6962 0.3995 0.3693 0.0372 1.0000 Uiso R . . . . .
H71 H 0.8337 0.6676 0.3351 0.0320 1.0000 Uiso R . . . . .
H82 H 0.4580 0.6283 0.2832 0.0333 1.0000 Uiso R . . . . .
H81 H 0.5560 0.6994 0.2022 0.0329 1.0000 Uiso R . . . . .
H91 H 0.3627 0.3968 0.2056 0.0343 1.0000 Uiso R . . . . .
H101 H 0.5550 0.2810 0.1013 0.0318 1.0000 Uiso R . . . . .
H112 H 0.9112 0.4079 0.1125 0.0311 1.0000 Uiso R . . . . .
H111 H 0.7710 0.4467 0.0245 0.0298 1.0000 Uiso R . . . . .
H121 H 0.9295 0.6933 0.0460 0.0296 1.0000 Uiso R . . . . .
H131 H 1.1513 0.7033 0.1612 0.0290 1.0000 Uiso R . . . . .
H141 H 1.0620 0.9090 0.2603 0.0369 1.0000 Uiso R . . . . .
H142 H 0.8205 0.9289 0.2111 0.0375 1.0000 Uiso R . . . . .
H152 H 1.0732 1.1473 0.1729 0.0613 1.0000 Uiso R . . . . .
H151 H 1.2244 0.9964 0.1428 0.0625 1.0000 Uiso R . . . . .
H153 H 0.9809 1.0347 0.0912 0.0610 1.0000 Uiso R . . . . .
H171 H 0.6295 0.8333 0.0354 0.0424 1.0000 Uiso R . . . . .
H161 H 0.3977 0.5850 0.0537 0.0469 1.0000 Uiso R . . . . .
H11 H 1.5294 0.5505 0.6677 0.0623 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          10.4(5)
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 . 1.184(4) yes
C1 . H11 . 0.924 no
C2 . C3 . 1.436(3) yes
C3 . C4 . 1.313(3) yes
C3 . H31 . 0.966 no
C4 . C5 . 1.504(3) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.526(3) yes
C5 . H51 . 0.970 no
C5 . H52 . 0.982 no
C6 . C7 . 1.527(3) yes
C6 . O21 . 1.444(2) yes
C6 . H61 . 0.984 no
C7 . C8 . 1.519(2) yes
C7 . O22 . 1.426(2) yes
C7 . H71 . 0.942 no
C8 . C9 . 1.530(3) yes
C8 . H82 . 0.976 no
C8 . H81 . 0.951 no
C9 . C10 . 1.534(3) yes
C9 . O21 . 1.442(2) yes
C9 . H91 . 0.963 no
C10 . C11 . 1.535(2) yes
C10 . O16 . 1.450(2) yes
C10 . H101 . 0.969 no
C11 . C12 . 1.535(2) yes
C11 . H112 . 0.960 no
C11 . H111 . 0.957 no
C12 . C13 . 1.558(2) yes
C12 . O17 . 1.449(2) yes
C12 . H121 . 0.977 no
C13 . C14 . 1.527(2) yes
C13 . O22 . 1.430(2) yes
C13 . H131 . 0.990 no
C14 . C15 . 1.521(3) yes
C14 . H141 . 0.970 no
C14 . H142 . 0.946 no
C15 . H152 . 0.971 no
C15 . H151 . 0.959 no
C15 . H153 . 0.985 no
O16 . H161 . 0.810 no
O17 . H171 . 0.822 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 . H11 . 174.9 no
C1 . C2 . C3 . 176.5(3) yes
C2 . C3 . C4 . 124.2(2) yes
C2 . C3 . H31 . 117.5 no
C4 . C3 . H31 . 118.3 no
C3 . C4 . C5 . 124.4(2) yes
C3 . C4 . H41 . 118.2 no
C5 . C4 . H41 . 117.4 no
C4 . C5 . C6 . 111.61(18) yes
C4 . C5 . H51 . 110.3 no
C6 . C5 . H51 . 109.7 no
C4 . C5 . H52 . 108.4 no
C6 . C5 . H52 . 107.2 no
H51 . C5 . H52 . 109.6 no
C5 . C6 . C7 . 116.73(17) yes
C5 . C6 . O21 . 108.70(16) yes
C7 . C6 . O21 . 103.89(14) yes
C5 . C6 . H61 . 109.1 no
C7 . C6 . H61 . 109.3 no
O21 . C6 . H61 . 108.7 no
C6 . C7 . C8 . 100.34(15) yes
C6 . C7 . O22 . 105.22(15) yes
C8 . C7 . O22 . 114.25(14) yes
C6 . C7 . H71 . 110.7 no
C8 . C7 . H71 . 112.7 no
O22 . C7 . H71 . 112.6 no
C7 . C8 . C9 . 102.63(15) yes
C7 . C8 . H82 . 108.5 no
C9 . C8 . H82 . 109.1 no
C7 . C8 . H81 . 113.0 no
C9 . C8 . H81 . 111.8 no
H82 . C8 . H81 . 111.4 no
C8 . C9 . C10 . 117.52(16) yes
C8 . C9 . O21 . 106.27(14) yes
C10 . C9 . O21 . 108.19(15) yes
C8 . C9 . H91 . 108.5 no
C10 . C9 . H91 . 106.9 no
O21 . C9 . H91 . 109.3 no
C9 . C10 . C11 . 120.06(15) yes
C9 . C10 . O16 . 108.35(14) yes
C11 . C10 . O16 . 109.41(15) yes
C9 . C10 . H101 . 105.1 no
C11 . C10 . H101 . 106.6 no
O16 . C10 . H101 . 106.4 no
C10 . C11 . C12 . 117.85(15) yes
C10 . C11 . H112 . 108.9 no
C12 . C11 . H112 . 108.5 no
C10 . C11 . H111 . 105.0 no
C12 . C11 . H111 . 105.8 no
H112 . C11 . H111 . 110.6 no
C11 . C12 . C13 . 112.21(14) yes
C11 . C12 . O17 . 110.28(14) yes
C13 . C12 . O17 . 114.19(14) yes
C11 . C12 . H121 . 104.4 no
C13 . C12 . H121 . 107.1 no
O17 . C12 . H121 . 108.1 no
C12 . C13 . C14 . 115.31(14) yes
C12 . C13 . O22 . 113.57(14) yes
C14 . C13 . O22 . 113.83(15) yes
C12 . C13 . H131 . 104.5 no
C14 . C13 . H131 . 104.5 no
O22 . C13 . H131 . 103.4 no
C13 . C14 . C15 . 111.68(16) yes
C13 . C14 . H141 . 107.3 no
C15 . C14 . H141 . 109.5 no
C13 . C14 . H142 . 110.2 no
C15 . C14 . H142 . 110.7 no
H141 . C14 . H142 . 107.3 no
C14 . C15 . H152 . 108.4 no
C14 . C15 . H151 . 106.9 no
H152 . C15 . H151 . 108.8 no
C14 . C15 . H153 . 112.5 no
H152 . C15 . H153 . 110.5 no
H151 . C15 . H153 . 109.6 no
C10 . O16 . H161 . 106.3 no
C12 . O17 . H171 . 110.8 no
C6 . O21 . C9 . 108.80(14) yes
C13 . O22 . C7 . 120.63(13) yes
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
C8 . H81 . O17 . 145 0.95 2.19 3.019(3) yes
O17 . H171 . C10 2_655 147 0.82 2.55 3.268(3) yes
O17 . H171 . O16 2_655 179 0.82 1.89 2.716(3) yes
O16 . H161 . O17 . 146 0.81 1.96 2.676(3) yes



# 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 8 8 x .
-1 1 2 x .
-1 -1 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_12
_database_code_depnum_ccdc_archive 'CCDC 2005092'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2019-11-20
_audit_creation_method           'CRYSTALS_ver_14.61_build_7356 '

_oxford_structure_analysis_title 7242
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.6615(2)
_cell_length_b                   9.1823(2)
_cell_length_c                   22.2795(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1362.79(6)

_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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 '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 = C13 H21 Br1 O3 
# Dc =      1.49 Fooo =    632.00 Mu =     40.78 M =    305.21
# Found Formula = C13 H21 Br1 O3 
# Dc =      1.49 FOOO =    632.00 Mu =     40.78 M =    305.21

_chemical_formula_sum            'C13 H21 Br O3'
_chemical_formula_moiety         'C13 H21 Br O3'
_chemical_compound_source        .
_chemical_formula_weight         305.21


_cell_measurement_reflns_used    14742
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      76.89
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.09
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    4.078

# Sheldrick geometric approximatio 0.52 0.69 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_T_max  0.69
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            23624
_diffrn_reflns_av_unetI/netI     0.031
_reflns_number_total             2891
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_sigmaI/netI    0.0315
# Number of reflections without Friedels Law is 2891 
# Number of reflections with Friedels Law is 1699 
# Theoretical number of reflections is about 1447 

_diffrn_reflns_theta_min         3.968
_diffrn_reflns_theta_max         77.356
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        77.356
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              28

_oxford_diffrn_Wilson_B_factor   2.66
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.46
_refine_diff_density_max         0.71


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

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2886
_oxford_refine_ls_R_factor_ref   0.0331
_refine_ls_wR_factor_ref         0.0923
_refine_ls_goodness_of_fit_ref   1.0686
_refine_ls_shift/su_max          0.0009912
_refine_ls_shift/su_mean         0.0000251


# Computed with no filters except I/sigma = -10 
_oxford_reflns_number_all        2886
_refine_ls_R_factor_all          0.0331
_refine_ls_wR_factor_all         0.0923

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2824
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0921

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  -0.047(9) # for 1181 Friedel pairs 
_oxford_Bijvoet_difference       -0.034(5) # for 1181 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.02(3) # for 1192 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.034(5)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1181 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 + 3.03P] 
 ,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
Br1 Br -0.02238(6) 0.61659(4) 0.601996(18) 0.0356 1.0000 Uani . . . . . .
C3 C 0.6350(8) -0.0974(6) 0.5784(2) 0.0497 1.0000 Uani . . . . . .
C4 C 0.4408(7) -0.1046(5) 0.5808(2) 0.0440 1.0000 Uani . . . . . .
C5 C 0.3050(6) -0.0558(5) 0.6315(2) 0.0364 1.0000 Uani . . . . . .
C6 C 0.3964(6) 0.0528(4) 0.67467(18) 0.0301 1.0000 Uani . . . . . .
C7 C 0.4530(5) 0.2022(4) 0.64931(16) 0.0267 1.0000 Uani . . . . . .
C8 C 0.4602(5) 0.2903(4) 0.70725(15) 0.0278 1.0000 Uani . . . . . .
C9 C 0.2820(5) 0.2320(4) 0.74324(17) 0.0268 1.0000 Uani . . . . . .
C10 C 0.0893(5) 0.3231(4) 0.74025(17) 0.0284 1.0000 Uani . . . . . .
C11 C 0.0050(5) 0.3645(4) 0.67900(15) 0.0274 1.0000 Uani . . . . . .
C12 C 0.1408(5) 0.4643(4) 0.64164(16) 0.0246 1.0000 Uani . . . . . .
C13 C 0.2587(5) 0.3845(4) 0.59191(15) 0.0258 1.0000 Uani . . . . . .
C14 C 0.4483(6) 0.4652(4) 0.57146(18) 0.0338 1.0000 Uani . . . . . .
C15 C 0.5458(7) 0.3905(5) 0.51773(18) 0.0441 1.0000 Uani . . . . . .
O16 O 0.2451(4) 0.0889(3) 0.71960(12) 0.0299 1.0000 Uani . . . . . .
O17 O 0.2956(3) 0.2369(3) 0.60873(12) 0.0253 1.0000 Uani . . . . . .
O18 O 0.1324(4) 0.4509(3) 0.77465(12) 0.0322 1.0000 Uani . . . . . .
H31 H 0.7044 -0.0596 0.6119 0.0603 1.0000 Uiso R . . . . .
H32 H 0.7022 -0.1311 0.5433 0.0601 1.0000 Uiso R . . . . .
H41 H 0.3793 -0.1439 0.5465 0.0528 1.0000 Uiso R . . . . .
H52 H 0.2705 -0.1413 0.6538 0.0437 1.0000 Uiso R . . . . .
H51 H 0.1844 -0.0116 0.6142 0.0440 1.0000 Uiso R . . . . .
H61 H 0.5109 0.0107 0.6944 0.0359 1.0000 Uiso R . . . . .
H71 H 0.5820 0.2021 0.6290 0.0318 1.0000 Uiso R . . . . .
H81 H 0.5861 0.2705 0.7275 0.0330 1.0000 Uiso R . . . . .
H82 H 0.4501 0.3943 0.6993 0.0318 1.0000 Uiso R . . . . .
H91 H 0.3181 0.2238 0.7857 0.0315 1.0000 Uiso R . . . . .
H101 H -0.0133 0.2665 0.7617 0.0343 1.0000 Uiso R . . . . .
H112 H -0.1184 0.4164 0.6855 0.0327 1.0000 Uiso R . . . . .
H111 H -0.0222 0.2762 0.6564 0.0332 1.0000 Uiso R . . . . .
H121 H 0.2313 0.5155 0.6690 0.0302 1.0000 Uiso R . . . . .
H131 H 0.1686 0.3812 0.5569 0.0304 1.0000 Uiso R . . . . .
H141 H 0.5418 0.4714 0.6047 0.0404 1.0000 Uiso R . . . . .
H142 H 0.4095 0.5628 0.5586 0.0411 1.0000 Uiso R . . . . .
H152 H 0.6680 0.4398 0.5073 0.0659 1.0000 Uiso R . . . . .
H153 H 0.5738 0.2903 0.5272 0.0657 1.0000 Uiso R . . . . .
H151 H 0.4561 0.3936 0.4844 0.0655 1.0000 Uiso R . . . . .
H181 H 0.0295 0.4966 0.7783 0.0480 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.76(16)
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
Br1 . C12 . 1.979(3) yes
C3 . C4 . 1.297(7) yes
C3 . H31 . 0.945 no
C3 . H32 . 0.953 no
C4 . C5 . 1.515(6) yes
C4 . H41 . 0.939 no
C5 . C6 . 1.514(6) yes
C5 . H52 . 0.957 no
C5 . H51 . 0.979 no
C6 . C7 . 1.531(5) yes
C6 . O16 . 1.458(4) yes
C6 . H61 . 0.961 no
C7 . C8 . 1.524(5) yes
C7 . O17 . 1.421(4) yes
C7 . H71 . 0.972 no
C8 . C9 . 1.529(5) yes
C8 . H81 . 0.970 no
C8 . H82 . 0.973 no
C9 . C10 . 1.534(5) yes
C9 . O16 . 1.437(5) yes
C9 . H91 . 0.980 no
C10 . C11 . 1.523(5) yes
C10 . O18 . 1.431(5) yes
C10 . H101 . 0.983 no
C11 . C12 . 1.534(5) yes
C11 . H112 . 0.961 no
C11 . H111 . 0.972 no
C12 . C13 . 1.543(5) yes
C12 . H121 . 0.978 no
C13 . C14 . 1.534(5) yes
C13 . O17 . 1.428(4) yes
C13 . H131 . 0.984 no
C14 . C15 . 1.525(5) yes
C14 . H141 . 0.969 no
C14 . H142 . 0.975 no
C15 . H152 . 0.960 no
C15 . H153 . 0.962 no
C15 . H151 . 0.954 no
O18 . H181 . 0.807 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
C4 . C3 . H31 . 118.4 no
C4 . C3 . H32 . 119.0 no
H31 . C3 . H32 . 122.6 no
C3 . C4 . C5 . 127.7(5) yes
C3 . C4 . H41 . 115.0 no
C5 . C4 . H41 . 117.4 no
C4 . C5 . C6 . 115.4(4) yes
C4 . C5 . H52 . 106.7 no
C6 . C5 . H52 . 107.9 no
C4 . C5 . H51 . 108.7 no
C6 . C5 . H51 . 107.8 no
H52 . C5 . H51 . 110.3 no
C5 . C6 . C7 . 117.0(3) yes
C5 . C6 . O16 . 108.0(3) yes
C7 . C6 . O16 . 102.7(3) yes
C5 . C6 . H61 . 110.2 no
C7 . C6 . H61 . 109.4 no
O16 . C6 . H61 . 109.0 no
C6 . C7 . C8 . 99.8(3) yes
C6 . C7 . O17 . 104.7(3) yes
C8 . C7 . O17 . 116.3(3) yes
C6 . C7 . H71 . 113.0 no
C8 . C7 . H71 . 111.6 no
O17 . C7 . H71 . 110.8 no
C7 . C8 . C9 . 103.5(3) yes
C7 . C8 . H81 . 108.8 no
C9 . C8 . H81 . 111.2 no
C7 . C8 . H82 . 111.4 no
C9 . C8 . H82 . 112.6 no
H81 . C8 . H82 . 109.2 no
C8 . C9 . C10 . 115.9(3) yes
C8 . C9 . O16 . 105.1(3) yes
C10 . C9 . O16 . 109.9(3) yes
C8 . C9 . H91 . 110.1 no
C10 . C9 . H91 . 106.8 no
O16 . C9 . H91 . 109.0 no
C9 . C10 . C11 . 118.9(3) yes
C9 . C10 . O18 . 104.8(3) yes
C11 . C10 . O18 . 110.4(3) yes
C9 . C10 . H101 . 105.8 no
C11 . C10 . H101 . 108.2 no
O18 . C10 . H101 . 108.2 no
C10 . C11 . C12 . 114.7(3) yes
C10 . C11 . H112 . 107.7 no
C12 . C11 . H112 . 106.8 no
C10 . C11 . H111 . 109.0 no
C12 . C11 . H111 . 109.1 no
H112 . C11 . H111 . 109.4 no
C11 . C12 . Br1 . 109.9(2) yes
C11 . C12 . C13 . 113.9(3) yes
Br1 . C12 . C13 . 107.1(2) yes
C11 . C12 . H121 . 108.2 no
Br1 . C12 . H121 . 106.1 no
C13 . C12 . H121 . 111.3 no
C12 . C13 . C14 . 113.8(3) yes
C12 . C13 . O17 . 110.5(3) yes
C14 . C13 . O17 . 113.2(3) yes
C12 . C13 . H131 . 105.9 no
C14 . C13 . H131 . 106.4 no
O17 . C13 . H131 . 106.5 no
C13 . C14 . C15 . 111.5(3) yes
C13 . C14 . H141 . 109.4 no
C15 . C14 . H141 . 110.6 no
C13 . C14 . H142 . 108.2 no
C15 . C14 . H142 . 107.3 no
H141 . C14 . H142 . 109.9 no
C14 . C15 . H152 . 109.8 no
C14 . C15 . H153 . 109.9 no
H152 . C15 . H153 . 109.9 no
C14 . C15 . H151 . 109.4 no
H152 . C15 . H151 . 109.1 no
H153 . C15 . H151 . 108.8 no
C6 . O16 . C9 . 110.0(3) yes
C13 . O17 . C7 . 120.5(3) yes
C10 . O18 . H181 . 108.0 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
C6 . H61 . O18 4_646 163 0.96 2.53 3.465(6) yes
O18 . H181 . O16 4_556 172 0.81 2.02 2.819(6) yes



# 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
0 9 1 x .
1 9 0 x .
-3 10 1 x .
1 10 1 x .
-1 10 1 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_18
_database_code_depnum_ccdc_archive 'CCDC 2005093'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-05-23
_audit_creation_method           CRYSTALS_ver_14.61_build_6156

_oxford_structure_analysis_title 6960
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.3606(3)
_cell_length_b                   13.1527(7)
_cell_length_c                   14.3775(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1581.01(15)

_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'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 '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 = C15 H15 Br1 O3 
# Dc =      1.36 Fooo =    656.00 Mu =     35.60 M =    323.19
# Found Formula = C15.00 H21.00 Br1.00 O3 
# Dc =      1.38 FOOO =    680.00 Mu =     35.61 M =    329.23

_chemical_formula_sum            'C15 H21 Br1 O3'
_chemical_formula_moiety         'C15 H21 Br1 O3'
_chemical_compound_source        .
_chemical_formula_weight         329.23


_cell_measurement_reflns_used    2431
_cell_measurement_theta_min      5
_cell_measurement_theta_max      75
_cell_measurement_temperature    250

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.28

_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             679.996
_exptl_absorpt_coefficient_mu    3.561

# Sheldrick geometric approximatio 0.75 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_T_max  0.93
_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      250
_diffrn_reflns_number            8437
_reflns_number_total             3256
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0666
# Number of reflections without Friedels Law is 3256 
# Number of reflections with Friedels Law is 1889 
# Theoretical number of reflections is about 1659 


_diffrn_reflns_theta_min         4.556
_diffrn_reflns_theta_max         76.390
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        74.098
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   6.47
_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         -0.30
_refine_diff_density_max         0.23


# 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         3256
_refine_ls_number_restraints     670
_refine_ls_number_parameters     274
_oxford_refine_ls_R_factor_ref   0.0592
_refine_ls_wR_factor_ref         0.1267
_refine_ls_goodness_of_fit_ref   1.0121
_refine_ls_shift/su_max          0.0005080
_refine_ls_shift/su_mean         0.0000483


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3256
_refine_ls_R_factor_all          0.0592
_refine_ls_wR_factor_all         0.1267

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2358
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_gt          0.1030

_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_abs_structure_details 'Flack (1983), 1367 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 + 0.21P] 
 ,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 -0.2183(3) 0.62233(17) 0.5365(2) 0.0709 1.0000 Uani . . . . . .
O2 O 0.0698(3) 0.54224(19) 0.63611(19) 0.0728 1.0000 Uani D . . . . .
O3 O -0.0365(3) 0.83215(17) 0.5253(2) 0.0728 1.0000 Uani . . . . . .
C1 C -0.0465(16) 0.0866(7) 0.5356(11) 0.1093 0.549(2) Uani D . P 1 1 .
C2 C -0.0430(7) 0.1758(5) 0.5295(5) 0.0972 0.549(2) Uani D . P 1 1 .
C3 C -0.0304(6) 0.2825(5) 0.5143(8) 0.0966 0.549(2) Uani D . P 1 1 .
C4 C -0.1452(7) 0.3460(4) 0.5145(7) 0.0912 0.549(2) Uani D . P 1 1 .
C5 C -0.1342(10) 0.4546(5) 0.4921(4) 0.0846 0.549(2) Uani D . P 1 1 .
C6 C -0.1884(5) 0.5198(2) 0.5705(3) 0.0764 1.0000 Uani D . . . . .
C7 C -0.0947(5) 0.5341(3) 0.6603(3) 0.0707 1.0000 Uani . . . . . .
C8 C -0.1626(4) 0.6334(3) 0.6954(3) 0.0667 1.0000 Uani . . . . . .
C9 C -0.1627(4) 0.6950(2) 0.6053(3) 0.0605 1.0000 Uani . . . . . .
C10 C 0.0001(4) 0.7400(2) 0.5750(2) 0.0613 1.0000 Uani D . . . . .
Br1 Br 0.3959(4) 0.7249(3) 0.7604(2) 0.1255 0.6304(17) Uani D . P 2 1 .
C11 C 0.1251(7) 0.7626(3) 0.6524(5) 0.0724 0.6304(17) Uani D . P 2 1 .
C12 C 0.2417(6) 0.6739(3) 0.6728(2) 0.0826 0.6304(17) Uani D . P 2 1 .
C13 C 0.1731(6) 0.5753(5) 0.7090(4) 0.0916 0.6304(17) Uani D . P 2 1 .
C14 C 0.3029(7) 0.4888(6) 0.7061(9) 0.1084 0.6304(17) Uani D . P 2 1 .
C15 C 0.2324(9) 0.3893(6) 0.7308(8) 0.1162 0.6304(17) Uani D . P 2 1 .
C101 C -0.0966(12) 0.0828(8) 0.5396(11) 0.0907 0.451(2) Uani D . P 1 2 .
C102 C -0.1001(7) 0.1693(5) 0.5173(7) 0.0904 0.451(2) Uani D . P 1 2 .
C103 C -0.1194(11) 0.2724(5) 0.4871(6) 0.0873 0.451(2) Uani D . P 1 2 .
C104 C -0.0552(11) 0.3521(5) 0.5250(7) 0.0870 0.451(2) Uani D . P 1 2 .
C105 C -0.0850(12) 0.4622(6) 0.4973(6) 0.0818 0.451(2) Uani D . P 1 2 .
Br101 Br 0.3705(5) 0.7510(4) 0.7766(3) 0.1039 0.3696(17) Uani D . P 2 2 .
C111 C 0.1077(10) 0.7679(5) 0.6539(6) 0.0630 0.3696(17) Uani D . P 2 2 .
C112 C 0.2347(9) 0.6915(4) 0.6741(3) 0.0743 0.3696(17) Uani D . P 2 2 .
C113 C 0.1822(8) 0.5825(6) 0.7015(6) 0.0729 0.3696(17) Uani D . P 2 2 .
C114 C 0.3299(10) 0.5166(7) 0.7263(13) 0.0874 0.3696(17) Uani D . P 2 2 .
C115 C 0.2809(13) 0.4203(10) 0.7711(12) 0.1002 0.3696(17) Uani D . P 2 2 .
H11 H -0.0501 0.0145 0.5393 0.1304 0.549(2) Uiso R . P 1 1 .
H31 H 0.0684 0.8473 0.5050 0.0875 1.0000 Uiso R . . . . .
H32 H 0.0733 0.3083 0.4999 0.1152 0.549(2) Uiso R . P 1 1 .
H41 H -0.2476 0.3206 0.5314 0.1085 0.549(2) Uiso R . P 1 1 .
H51 H -0.0261 0.4708 0.4778 0.1018 0.549(2) Uiso R . P 1 1 .
H52 H -0.1995 0.4682 0.4395 0.1018 0.549(2) Uiso R . P 1 1 .
H61 H -0.2898 0.4939 0.5886 0.0920 0.549(2) Uiso R . P 1 1 .
H62 H -0.2860 0.4850 0.5818 0.0920 0.451(2) Uiso R . P 1 2 .
H71 H -0.1131 0.4802 0.7029 0.0849 1.0000 Uiso R . . . . .
H81 H -0.0956 0.6633 0.7412 0.0800 1.0000 Uiso DR . . . . .
H82 H -0.2674 0.6254 0.7199 0.0800 1.0000 Uiso R . . . . .
H91 H -0.2387 0.7485 0.6105 0.0726 1.0000 Uiso R . . . . .
H101 H 0.0494 0.6937 0.5331 0.0733 0.6304(17) Uiso R . P 2 1 .
H102 H 0.0496 0.6939 0.5334 0.0733 0.3696(17) Uiso R . P 2 2 .
H111 H 0.1813 0.8248 0.6444 0.0740 0.6304(17) Uiso R . P 2 1 .
H112 H 0.0607 0.7666 0.7068 0.0740 0.6304(17) Uiso DR . P 2 1 .
H121 H 0.2930 0.6621 0.6148 0.0803 0.6304(17) Uiso R . P 2 1 .
H131 H 0.1201 0.5798 0.7673 0.1073 0.6304(17) Uiso R . P 2 1 .
H141 H 0.3832 0.5065 0.7500 0.1507 0.6304(17) Uiso R . P 2 1 .
H142 H 0.3484 0.4865 0.6456 0.1507 0.6304(17) Uiso R . P 2 1 .
H151 H 0.3161 0.3404 0.7292 0.1582 0.6304(17) Uiso R . P 2 1 .
H152 H 0.1871 0.3912 0.7913 0.1582 0.6304(17) Uiso R . P 2 1 .
H153 H 0.1523 0.3712 0.6869 0.1582 0.6304(17) Uiso R . P 2 1 .
H1011 H -0.0968 0.0134 0.5581 0.1080 0.451(2) Uiso R . P 1 2 .
H1031 H -0.1884 0.2836 0.4356 0.1029 0.451(2) Uiso R . P 1 2 .
H1041 H 0.0183 0.3407 0.5743 0.1042 0.451(2) Uiso R . P 1 2 .
H1051 H 0.0149 0.4960 0.4912 0.0981 0.451(2) Uiso R . P 1 2 .
H1052 H -0.1394 0.4632 0.4394 0.0981 0.451(2) Uiso R . P 1 2 .
H1111 H 0.0533 0.7891 0.7085 0.0689 0.3696(17) Uiso R . P 2 2 .
H1112 H 0.1639 0.8239 0.6280 0.0689 0.3696(17) Uiso R . P 2 2 .
H1121 H 0.3041 0.6815 0.6226 0.0908 0.3696(17) Uiso R . P 2 2 .
H1131 H 0.1275 0.5911 0.7589 0.0748 0.3696(17) Uiso R . P 2 2 .
H1141 H 0.4061 0.5471 0.7666 0.1100 0.3696(17) Uiso R . P 2 2 .
H1142 H 0.3793 0.5005 0.6687 0.1100 0.3696(17) Uiso R . P 2 2 .
H1151 H 0.3674 0.3748 0.7812 0.1598 0.3696(17) Uiso R . P 2 2 .
H1152 H 0.2316 0.4359 0.8288 0.1598 0.3696(17) Uiso R . P 2 2 .
H1153 H 0.2048 0.3894 0.7309 0.1598 0.3696(17) Uiso R . P 2 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.25(17)
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 . C6 . 1.456(4) yes
O1 . C9 . 1.453(4) yes
O2 . C7 . 1.422(5) yes
O2 . C13 . 1.4262(19) yes
O2 . C7 . 1.422(5) yes
O2 . C113 . 1.4310(19) yes
O3 . C10 . 1.441(4) yes
O3 . H31 . 0.946 no
C1 . C2 . 1.176(8) yes
C1 . H11 . 0.950 no
C2 . C3 . 1.424(7) yes
C3 . C4 . 1.272(7) yes
C3 . H32 . 0.954 no
C4 . C5 . 1.468(7) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.487(7) yes
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C6 . C7 . 1.522(6) yes
C6 . H61 . 0.950 no
C6 . C7 . 1.522(6) yes
C6 . C105 . 1.558(7) yes
C6 . H62 . 0.950 no
C7 . C8 . 1.510(5) yes
C7 . H71 . 0.950 no
C8 . C9 . 1.529(5) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . C10 . 1.546(4) yes
C9 . H91 . 0.950 no
C10 . C11 . 1.556(6) yes
C10 . H101 . 0.950 no
C10 . C111 . 1.493(6) yes
C10 . H102 . 0.948 no
Br1 . C12 . 1.924(4) yes
C11 . C12 . 1.549(6) yes
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C12 . C13 . 1.510(6) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.573(7) yes
C13 . H131 . 0.950 no
C14 . C15 . 1.478(7) yes
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C15 . H151 . 0.950 no
C15 . H152 . 0.950 no
C15 . H153 . 0.950 no
C101 . C102 . 1.182(8) yes
C101 . H1011 . 0.950 no
C102 . C103 . 1.434(7) yes
C103 . C104 . 1.298(8) yes
C103 . H1031 . 0.950 no
C104 . C105 . 1.522(7) yes
C104 . H1041 . 0.950 no
C105 . H1051 . 0.950 no
C105 . H1052 . 0.950 no
Br101 . C112 . 2.018(6) yes
C111 . C112 . 1.490(7) yes
C111 . H1111 . 0.950 no
C111 . H1112 . 0.950 no
C112 . C113 . 1.551(7) yes
C112 . H1121 . 0.950 no
C113 . C114 . 1.550(8) yes
C113 . H1131 . 0.950 no
C114 . C115 . 1.479(9) yes
C114 . H1141 . 0.950 no
C114 . H1142 . 0.950 no
C115 . H1151 . 0.950 no
C115 . H1152 . 0.950 no
C115 . H1153 . 0.950 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
C6 . O1 . C9 . 109.0(3) yes
C7 . O2 . C13 . 115.4(4) yes
C7 . O2 . C113 . 120.1(5) yes
C10 . O3 . H31 . 97.7 no
C2 . C1 . H11 . 178.9 no
C1 . C2 . C3 . 174.59(10) yes
C2 . C3 . C4 . 126.20(10) yes
C2 . C3 . H32 . 116.9 no
C4 . C3 . H32 . 116.9 no
C3 . C4 . C5 . 126.23(10) yes
C3 . C4 . H41 . 116.7 no
C5 . C4 . H41 . 117.1 no
C4 . C5 . C6 . 112.08(10) yes
C4 . C5 . H51 . 108.9 no
C6 . C5 . H51 . 108.9 no
C4 . C5 . H52 . 108.7 no
C6 . C5 . H52 . 108.7 no
H51 . C5 . H52 . 109.5 no
C5 . C6 . O1 . 109.4(4) yes
C5 . C6 . C7 . 123.9(5) yes
O1 . C6 . C7 . 105.0(3) yes
C5 . C6 . H61 . 105.9 no
O1 . C6 . H61 . 105.7 no
C7 . C6 . H61 . 105.7 no
O1 . C6 . C7 . 105.0(3) yes
O1 . C6 . C105 . 108.6(4) yes
C7 . C6 . C105 . 110.3(5) yes
O1 . C6 . H62 . 110.9 no
C7 . C6 . H62 . 110.9 no
C105 . C6 . H62 . 111.0 no
C6 . C7 . O2 . 107.4(3) yes
C6 . C7 . C8 . 101.4(3) yes
O2 . C7 . C8 . 112.4(3) yes
C6 . C7 . H71 . 111.8 no
O2 . C7 . H71 . 111.8 no
C8 . C7 . H71 . 111.6 no
C7 . C8 . C9 . 100.1(3) yes
C7 . C8 . H81 . 111.6 no
C9 . C8 . H81 . 111.5 no
C7 . C8 . H82 . 112.0 no
C9 . C8 . H82 . 111.9 no
H81 . C8 . H82 . 109.5 no
C8 . C9 . O1 . 103.2(3) yes
C8 . C9 . C10 . 116.2(3) yes
O1 . C9 . C10 . 109.9(3) yes
C8 . C9 . H91 . 109.1 no
O1 . C9 . H91 . 109.1 no
C10 . C9 . H91 . 109.1 no
C9 . C10 . O3 . 105.9(2) yes
C9 . C10 . C11 . 117.6(4) yes
O3 . C10 . C11 . 109.7(3) yes
C9 . C10 . H101 . 108.4 no
O3 . C10 . H101 . 108.4 no
C11 . C10 . H101 . 106.5 no
C9 . C10 . O3 . 105.9(2) yes
C9 . C10 . C111 . 114.2(5) yes
O3 . C10 . C111 . 107.3(4) yes
C9 . C10 . H102 . 108.6 no
O3 . C10 . H102 . 108.5 no
C111 . C10 . H102 . 112.0 no
C10 . C11 . C12 . 114.44(9) yes
C10 . C11 . H111 . 114.2 no
C12 . C11 . H111 . 111.1 no
C10 . C11 . H112 . 102.6 no
C12 . C11 . H112 . 104.0 no
H111 . C11 . H112 . 109.5 no
C11 . C12 . Br1 . 106.43(9) yes
C11 . C12 . C13 . 118.25(9) yes
Br1 . C12 . C13 . 109.15(9) yes
C11 . C12 . H121 . 103.9 no
Br1 . C12 . H121 . 109.2 no
C13 . C12 . H121 . 109.5 no
C12 . C13 . O2 . 103.8(4) yes
C12 . C13 . C14 . 110.48(9) yes
O2 . C13 . C14 . 100.3(5) yes
C12 . C13 . H131 . 115.3 no
O2 . C13 . H131 . 112.7 no
C14 . C13 . H131 . 113.0 no
C13 . C14 . C15 . 111.04(10) yes
C13 . C14 . H141 . 107.0 no
C15 . C14 . H141 . 109.9 no
C13 . C14 . H142 . 108.9 no
C15 . C14 . H142 . 110.5 no
H141 . C14 . H142 . 109.5 no
C14 . C15 . H151 . 107.4 no
C14 . C15 . H152 . 110.8 no
H151 . C15 . H152 . 109.5 no
C14 . C15 . H153 . 110.1 no
H151 . C15 . H153 . 109.5 no
H152 . C15 . H153 . 109.5 no
C102 . C101 . H1011 . 178.5 no
C101 . C102 . C103 . 174.57(10) yes
C102 . C103 . C104 . 126.22(10) yes
C102 . C103 . H1031 . 116.8 no
C104 . C103 . H1031 . 116.9 no
C103 . C104 . C105 . 126.26(10) yes
C103 . C104 . H1041 . 116.9 no
C105 . C104 . H1041 . 116.8 no
C6 . C105 . C104 . 112.18(10) yes
C6 . C105 . H1051 . 108.8 no
C104 . C105 . H1051 . 109.0 no
C6 . C105 . H1052 . 108.7 no
C104 . C105 . H1052 . 108.7 no
H1051 . C105 . H1052 . 109.5 no
C10 . C111 . C112 . 114.34(10) yes
C10 . C111 . H1111 . 114.4 no
C112 . C111 . H1111 . 112.2 no
C10 . C111 . H1112 . 101.0 no
C112 . C111 . H1112 . 104.2 no
H1111 . C111 . H1112 . 109.5 no
C111 . C112 . Br101 . 106.41(10) yes
C111 . C112 . C113 . 118.13(10) yes
Br101 . C112 . C113 . 109.43(10) yes
C111 . C112 . H1121 . 112.1 no
Br101 . C112 . H1121 . 106.2 no
C113 . C112 . H1121 . 104.0 no
C112 . C113 . O2 . 111.2(5) yes
C112 . C113 . C114 . 110.52(10) yes
O2 . C113 . C114 . 117.9(8) yes
C112 . C113 . H1131 . 104.2 no
O2 . C113 . H1131 . 107.4 no
C114 . C113 . H1131 . 104.6 no
C113 . C114 . C115 . 111.02(10) yes
C113 . C114 . H1141 . 116.0 no
C115 . C114 . H1141 . 106.4 no
C113 . C114 . H1142 . 105.7 no
C115 . C114 . H1142 . 108.0 no
H1141 . C114 . H1142 . 109.5 no
C114 . C115 . H1151 . 113.3 no
C114 . C115 . H1152 . 108.3 no
H1151 . C115 . H1152 . 109.5 no
C114 . C115 . H1153 . 106.7 no
H1151 . C115 . H1153 . 109.5 no
H1152 . C115 . H1153 . 109.5 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
C1 . H11 . O3 1_545 171 0.95 2.41 3.351(10) yes
C101 . H11 . O3 1_545 159 0.98 2.41 3.341(10) yes
O3 . H31 . O1 3_566 180 0.95 1.92 2.868(10) yes
C12 . H121 . O3 3_566 166 0.95 2.47 3.399(10) yes
C112 . H121 . O3 3_566 156 1.06 2.47 3.461(10) yes
C1 . H1011 . O3 1_545 135 1.10 2.48 3.351(10) yes
C101 . H1011 . O3 1_545 150 0.95 2.48 3.341(10) yes
C12 . H1121 . O3 3_566 169 0.90 2.52 3.399(10) yes
C112 . H1121 . O3 3_566 173 0.95 2.52 3.461(10) yes


####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 2005094'
loop_
_audit_author_name
_audit_author_address
'Amber Thompson'
;Chemical Crystallography Oxford
United Kingdom
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-04-23
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 6955
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   5.9422(2)
_cell_length_b                   7.6020(2)
_cell_length_c                   14.7513(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.005(2)
_cell_angle_gamma                90
_cell_volume                     654.10(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 = C13 H22 O4 
# Dc =      1.23 Fooo =    264.00 Mu =      7.34 M =    242.32
# Found Formula = C13.00 H22.00 O4 
# Dc =      1.23 FOOO =    264.00 Mu =      7.34 M =    242.32

_chemical_formula_sum            'C13 H22 O4'
_chemical_formula_moiety         'C13 H22 O4'
_chemical_compound_source        .
_chemical_formula_weight         242.32


_cell_measurement_reflns_used    7384
_cell_measurement_theta_min      6
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.06
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.734

# Sheldrick geometric approximatio 0.94 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_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 (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_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            13847
_reflns_number_total             2731
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_sigmaI/netI    0.0507
# Number of reflections without Friedels Law is 2731 
# Number of reflections with Friedels Law is 1481 
# Theoretical number of reflections is about 1378 


_diffrn_reflns_theta_min         6.112
_diffrn_reflns_theta_max         76.695
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        75.161
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   3.09
_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         -0.37
_refine_diff_density_max         0.41


# 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_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_restraints     5
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2730
_oxford_refine_ls_R_factor_ref   0.0586
_refine_ls_wR_factor_ref         0.1537
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_shift/su_max          0.0001375
_refine_ls_shift/su_mean         0.0000176


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2730
_refine_ls_R_factor_all          0.0586
_refine_ls_wR_factor_all         0.1537

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2643
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_gt          0.1495

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661?683 
_oxford_Hooft_y                  0.11(13) # for 1157 Friedel pairs 
_oxford_Bijvoet_difference       -0.01(9) # for 1157 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          -0.15(19) # for 1250 Friedel pairs 
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1157 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) + ( 0.13P)² + 0.03P] 
 ,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
C6 C 0.3921(4) 0.2241(3) 0.36917(14) 0.0414 1.0000 Uani . . . . . .
C7 C 0.3714(3) 0.3924(3) 0.31164(12) 0.0336 1.0000 Uani . . . . . .
C8 C 0.1236(3) 0.3749(3) 0.26072(12) 0.0349 1.0000 Uani . . . . . .
C9 C 0.1018(3) 0.1768(3) 0.24113(13) 0.0363 1.0000 Uani . . . . . .
C10 C 0.1171(3) 0.1187(3) 0.14301(13) 0.0330 1.0000 Uani . . . . . .
C11 C 0.3233(3) 0.1786(3) 0.10234(12) 0.0303 1.0000 Uani . . . . . .
C12 C 0.3520(3) 0.3766(3) 0.08709(12) 0.0316 1.0000 Uani . . . . . .
C13 C 0.5135(3) 0.4681(3) 0.16858(13) 0.0324 1.0000 Uani . . . . . .
C14 C 0.4688(4) 0.6658(3) 0.17617(18) 0.0436 1.0000 Uani . . . . . .
C15 C 0.6638(5) 0.7580(3) 0.2414(3) 0.0633 1.0000 Uani . . . . . .
O1 O 0.2833(3) 0.0941(2) 0.30520(10) 0.0413 1.0000 Uani . . . . . .
O2 O 0.5389(2) 0.3770(2) 0.25447(8) 0.0299 1.0000 Uani . . . . . .
O17 O 0.1300(2) 0.4581(2) 0.06156(10) 0.0378 1.0000 Uani D . . . . .
O16 O -0.0946(2) 0.1696(2) 0.08309(10) 0.0403 1.0000 Uani D . . . . .
C103 C 0.8782(11) 0.2979(9) 0.5530(5) 0.0501 0.490(11) Uani . . P 1 2 .
C3 C 0.8819(11) 0.3623(13) 0.5172(6) 0.0624 0.510(11) Uani . . P 1 1 .
C4 C 0.7001(9) 0.2619(7) 0.5023(3) 0.0459 0.510(11) Uani . . P 1 1 .
C104 C 0.7844(7) 0.3138(6) 0.4651(4) 0.0366 0.490(11) Uani . . P 1 2 .
C5 C 0.6324(4) 0.1643(3) 0.41192(15) 0.0479 1.0000 Uani . . . . . .
H61 H 0.2984 0.2351 0.4183 0.0502 1.0000 Uiso R . . . . .
H71 H 0.3968 0.4979 0.3488 0.0397 1.0000 Uiso R . . . . .
H82 H 0.0212 0.4080 0.3005 0.0415 1.0000 Uiso R . . . . .
H81 H 0.0896 0.4443 0.2050 0.0410 1.0000 Uiso R . . . . .
H91 H -0.0438 0.1327 0.2562 0.0435 1.0000 Uiso R . . . . .
H101 H 0.1217 -0.0081 0.1433 0.0398 1.0000 Uiso R . . . . .
H111 H 0.4588 0.1342 0.1425 0.0358 1.0000 Uiso R . . . . .
H112 H 0.3065 0.1267 0.0419 0.0350 1.0000 Uiso R . . . . .
H121 H 0.4287 0.3892 0.0360 0.0387 1.0000 Uiso R . . . . .
H131 H 0.6631 0.4597 0.1522 0.0386 1.0000 Uiso R . . . . .
H142 H 0.4520 0.7206 0.1164 0.0525 1.0000 Uiso R . . . . .
H141 H 0.3282 0.6830 0.1986 0.0512 1.0000 Uiso R . . . . .
H151 H 0.6241 0.8763 0.2518 0.0947 1.0000 Uiso R . . . . .
H152 H 0.7954 0.7560 0.2141 0.0947 1.0000 Uiso R . . . . .
H153 H 0.6964 0.6999 0.2997 0.0948 1.0000 Uiso R . . . . .
H1031 H 0.9581 0.3916 0.5846 0.0598 0.490(11) Uiso R . P 1 2 .
H1032 H 0.8642 0.1917 0.5831 0.0601 0.490(11) Uiso R . P 1 2 .
H32 H 0.9366 0.4090 0.5756 0.0749 0.510(11) Uiso R . P 1 1 .
H31 H 0.9615 0.3903 0.4703 0.0750 0.510(11) Uiso R . P 1 1 .
H41 H 0.6108 0.2506 0.5478 0.0548 0.510(11) Uiso R . P 1 1 .
H1041 H 0.8067 0.4190 0.4344 0.0435 0.490(11) Uiso R . P 1 2 .
H52 H 0.6266 0.0390 0.4246 0.0569 0.510(11) Uiso R . P 1 1 .
H54 H 0.7387 0.1839 0.3694 0.0568 0.510(11) Uiso R . P 1 1 .
H53 H 0.6225 0.0659 0.4533 0.0568 0.490(11) Uiso R . P 1 2 .
H51 H 0.7062 0.1249 0.3620 0.0564 0.490(11) Uiso R . P 1 2 .
H171 H 0.103(6) 0.522(4) 0.0172(17) 0.057(2) 1.0000 Uiso D . . . . .
H161 H -0.092(6) 0.272(3) 0.068(2) 0.060(2) 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          9.3(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
C6 . C7 . 1.527(3) yes
C6 . O1 . 1.433(3) yes
C6 . C5 . 1.517(3) yes
C6 . H61 . 0.998 no
C7 . C8 . 1.526(2) yes
C7 . O2 . 1.427(2) yes
C7 . H71 . 0.967 no
C8 . C9 . 1.534(3) yes
C8 . H82 . 0.956 no
C8 . H81 . 0.965 no
C9 . C10 . 1.533(3) yes
C9 . O1 . 1.437(2) yes
C9 . H91 . 0.992 no
C10 . C11 . 1.532(2) yes
C10 . O16 . 1.445(2) yes
C10 . H101 . 0.964 no
C11 . C12 . 1.537(3) yes
C11 . H111 . 0.965 no
C11 . H112 . 0.962 no
C12 . C13 . 1.552(2) yes
C12 . O17 . 1.441(2) yes
C12 . H121 . 0.957 no
C13 . C14 . 1.534(3) yes
C13 . O2 . 1.426(2) yes
C13 . H131 . 0.967 no
C14 . C15 . 1.527(3) yes
C14 . H142 . 0.963 no
C14 . H141 . 0.965 no
C15 . H151 . 0.950 no
C15 . H152 . 0.946 no
C15 . H153 . 0.953 no
O17 . H171 . 0.805(18) no
O16 . H161 . 0.812(18) no
C103 . C104 . 1.315(9) yes
C103 . H1031 . 0.930 no
C103 . H1032 . 0.933 no
C3 . C4 . 1.307(11) yes
C3 . H32 . 0.932 no
C3 . H31 . 0.933 no
C4 . C5 . 1.512(5) yes
C4 . H41 . 0.935 no
C104 . C5 . 1.566(5) yes
C104 . H1041 . 0.941 no
C5 . H52 . 0.973 no
C5 . H54 . 0.982 no
C5 . H53 . 0.974 no
C5 . H51 . 0.974 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
C7 . C6 . O1 . 103.51(15) yes
C7 . C6 . C5 . 116.87(19) yes
O1 . C6 . C5 . 109.70(18) yes
C7 . C6 . H61 . 109.7 no
O1 . C6 . H61 . 107.0 no
C5 . C6 . H61 . 109.5 no
C6 . C7 . C8 . 99.70(16) yes
C6 . C7 . O2 . 105.59(15) yes
C8 . C7 . O2 . 114.75(14) yes
C6 . C7 . H71 . 113.1 no
C8 . C7 . H71 . 112.5 no
O2 . C7 . H71 . 110.6 no
C7 . C8 . C9 . 102.53(15) yes
C7 . C8 . H82 . 110.1 no
C9 . C8 . H82 . 109.4 no
C7 . C8 . H81 . 113.4 no
C9 . C8 . H81 . 112.3 no
H82 . C8 . H81 . 109.0 no
C8 . C9 . C10 . 116.29(16) yes
C8 . C9 . O1 . 106.27(15) yes
C10 . C9 . O1 . 108.80(15) yes
C8 . C9 . H91 . 109.6 no
C10 . C9 . H91 . 109.0 no
O1 . C9 . H91 . 106.4 no
C9 . C10 . C11 . 118.71(15) yes
C9 . C10 . O16 . 107.37(14) yes
C11 . C10 . O16 . 110.40(15) yes
C9 . C10 . H101 . 106.9 no
C11 . C10 . H101 . 105.9 no
O16 . C10 . H101 . 106.9 no
C10 . C11 . C12 . 117.88(14) yes
C10 . C11 . H111 . 107.0 no
C12 . C11 . H111 . 109.2 no
C10 . C11 . H112 . 107.0 no
C12 . C11 . H112 . 105.1 no
H111 . C11 . H112 . 110.6 no
C11 . C12 . C13 . 113.28(14) yes
C11 . C12 . O17 . 109.77(14) yes
C13 . C12 . O17 . 114.17(15) yes
C11 . C12 . H121 . 107.2 no
C13 . C12 . H121 . 104.3 no
O17 . C12 . H121 . 107.5 no
C12 . C13 . C14 . 113.93(16) yes
C12 . C13 . O2 . 114.53(15) yes
C14 . C13 . O2 . 113.67(17) yes
C12 . C13 . H131 . 103.8 no
C14 . C13 . H131 . 105.2 no
O2 . C13 . H131 . 104.1 no
C13 . C14 . C15 . 111.98(17) yes
C13 . C14 . H142 . 110.3 no
C15 . C14 . H142 . 108.2 no
C13 . C14 . H141 . 109.3 no
C15 . C14 . H141 . 108.9 no
H142 . C14 . H141 . 108.1 no
C14 . C15 . H151 . 110.7 no
C14 . C15 . H152 . 108.3 no
H151 . C15 . H152 . 109.5 no
C14 . C15 . H153 . 110.8 no
H151 . C15 . H153 . 107.9 no
H152 . C15 . H153 . 109.6 no
C9 . O1 . C6 . 108.58(16) yes
C7 . O2 . C13 . 121.17(13) yes
C12 . O17 . H171 . 120(3) no
C10 . O16 . H161 . 111(2) no
C104 . C103 . H1031 . 120.2 no
C104 . C103 . H1032 . 119.3 no
H1031 . C103 . H1032 . 120.5 no
C4 . C3 . H32 . 120.6 no
C4 . C3 . H31 . 121.9 no
H32 . C3 . H31 . 117.5 no
C3 . C4 . C5 . 120.5(6) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 119.7 no
C103 . C104 . C5 . 121.5(5) yes
C103 . C104 . H1041 . 118.7 no
C5 . C104 . H1041 . 119.8 no
C6 . C5 . C4 . 106.9(2) yes
C6 . C5 . H52 . 108.0 no
C4 . C5 . H52 . 108.9 no
C6 . C5 . H54 . 111.0 no
C4 . C5 . H54 . 113.1 no
H52 . C5 . H54 . 108.8 no
C6 . C5 . C104 . 113.4(2) yes
C6 . C5 . H53 . 109.0 no
C104 . C5 . H53 . 110.0 no
C6 . C5 . H51 . 107.6 no
C104 . C5 . H51 . 107.6 no
H53 . C5 . H51 . 109.1 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
C8 . H81 . O17 . 144 0.96 2.18 3.013(5) yes
O17 . H171 . C10 2_555 155(3) 0.805 2.581 3.326(5) yes
O17 . H171 . O16 2_555 170(4) 0.805 1.851 2.648(5) yes
O16 . H161 . O17 . 140(3) 0.812 1.946 2.618(5) yes



# 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
-6 -1 11 x .
