# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_parent_domain
_database_code_depnum_ccdc_archive 'CCDC 1825187'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 O4'
_chemical_formula_weight         172.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6272(17)
_cell_length_b                   8.095(3)
_cell_length_c                   9.638(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.656(4)
_cell_angle_gamma                90
_cell_volume                     420.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    1142
_cell_measurement_theta_min      3.347
_cell_measurement_theta_max      26.021

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   0.470073
_exptl_transmission_factor_max   0.745566
_exptl_crystal_size_max          0.595
_exptl_crystal_size_mid          0.398
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART Breeze'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            870
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.347
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             870
_reflns_number_gt                686
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1584P)²+0.0960P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         870
_refine_ls_number_parameters     56
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.2460
_refine_ls_wR_factor_gt          0.2301
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5622(5) 0.5363(3) 0.3652(3) 0.0453(8) Uani 1 1 d . . . . .
H1 H 0.6986 0.6143 0.4034 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6383(6) 0.3738(4) 0.4435(3) 0.0541(9) Uani 1 1 d . . . . .
H2A H 0.7950 0.3380 0.4305 0.065 Uiso 1 1 calc R U . . .
H2B H 0.5147 0.2903 0.4019 0.065 Uiso 1 1 calc R U . . .
C3 C 0.6649(6) 0.3906(4) 0.6060(3) 0.0583(9) Uani 1 1 d . . . . .
H3A H 0.6960 0.2824 0.6508 0.070 Uiso 1 1 calc R U . . .
H3B H 0.8069 0.4600 0.6502 0.070 Uiso 1 1 calc R U . . .
C4 C 0.5314(5) 0.5186(3) 0.2043(3) 0.0428(7) Uani 1 1 d . . . . .
O1 O 0.7154(4) 0.4473(3) 0.1726(2) 0.0654(8) Uani 1 1 d . . . . .
H1A H 0.6861 0.4416 0.0844 0.098 Uiso 1 1 calc R U . . .
O2 O 0.3492(4) 0.5705(3) 0.1112(2) 0.0647(8) Uani 1 1 d . . . . .

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 0.0543(16) 0.0563(17) 0.0274(14) -0.0014(11) 0.0153(11) 0.0000(12)
C2 0.0710(18) 0.0659(18) 0.0299(15) 0.0045(12) 0.0214(13) 0.0233(14)
C3 0.0728(19) 0.079(2) 0.0259(14) 0.0078(12) 0.0177(13) 0.0293(16)
C4 0.0569(15) 0.0482(14) 0.0278(13) 0.0028(10) 0.0193(12) 0.0065(11)
O1 0.0738(15) 0.0989(19) 0.0297(11) 0.0068(10) 0.0250(11) 0.0287(12)
O2 0.0710(15) 0.0977(18) 0.0272(11) 0.0057(10) 0.0170(10) 0.0290(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.505(4) 3_666 ?
C1 C2 1.516(4) . ?
C1 C4 1.517(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.535(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C1 1.505(4) 3_666 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.227(3) . ?
C4 O1 1.295(3) . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 112.5(2) 3_666 . ?
C3 C1 C4 111.8(2) 3_666 . ?
C2 C1 C4 111.1(2) . . ?
C3 C1 H1 107.0 3_666 . ?
C2 C1 H1 107.0 . . ?
C4 C1 H1 107.0 . . ?
C1 C2 C3 111.2(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C1 C3 C2 112.5(2) 3_666 . ?
C1 C3 H3A 109.1 3_666 . ?
C2 C3 H3A 109.1 . . ?
C1 C3 H3B 109.1 3_666 . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
O2 C4 O1 122.5(2) . . ?
O2 C4 C1 122.8(2) . . ?
O1 C4 C1 114.7(2) . . ?
C4 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.221

_shelx_res_file                  
;

    twin5_a.res created by SHELXL-2014/7

TITL twin5_a.res in P2(1)/n
CELL  0.71073   5.6272   8.0951   9.6383   90.000  106.656   90.000
ZERR    2.000   0.0017   0.0025   0.0029    0.000    0.004    0.000
LATT 1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C  H  O
UNIT 16  24  8
L.S. 30
ACTA
BOND $H
FMAP 2
PLAN 10
size 0.595 0.398 0.330
TEMP 25.000
WGHT    0.158400    0.096000
BASF   0.21747
FVAR       1.97231
C1    1    0.562231    0.536341    0.365197    11.00000    0.05426    0.05630 =
         0.02744   -0.00138    0.01529    0.00004
AFIX  13
H1    2    0.698614    0.614262    0.403379    11.00000   -1.20000
AFIX   0
C2    1    0.638281    0.373795    0.443538    11.00000    0.07103    0.06586 =
         0.02988    0.00455    0.02139    0.02334
AFIX  23
H2A   2    0.794997    0.338013    0.430503    11.00000   -1.20000
H2B   2    0.514707    0.290341    0.401931    11.00000   -1.20000
AFIX   0
C3    1    0.664876    0.390561    0.605960    11.00000    0.07278    0.07854 =
         0.02593    0.00779    0.01769    0.02934
AFIX  23
H3A   2    0.695987    0.282391    0.650811    11.00000   -1.20000
H3B   2    0.806869    0.459985    0.650231    11.00000   -1.20000
AFIX   0
C4    1    0.531417    0.518569    0.204307    11.00000    0.05694    0.04825 =
         0.02780    0.00277    0.01926    0.00648
O1    3    0.715353    0.447343    0.172648    11.00000    0.07383    0.09887 =
         0.02969    0.00679    0.02498    0.02873
AFIX  83
H1A   2    0.686098    0.441556    0.084406    11.00000   -1.50000
AFIX   0
O2    3    0.349246    0.570526    0.111230    11.00000    0.07101    0.09774 =
         0.02723    0.00566    0.01701    0.02903
HKLF 5

REM  twin5_a.res in P2(1)/n
REM R1 =  0.0925 for     686 Fo > 4sig(Fo)  and  0.1044 for all     870 data
REM     56 parameters refined using      0 restraints

END

WGHT      0.1584      0.0960

REM Highest difference peak  0.370,  deepest hole -0.689,  1-sigma level  0.221
Q1    1   0.5819  0.2151  0.6243  11.00000  0.05    0.37
Q2    1   0.7154  0.2594  0.4232  11.00000  0.05    0.33
Q3    1   0.9747  0.3861  0.4388  11.00000  0.05    0.33
Q4    1   0.8202  0.3257  0.6680  11.00000  0.05    0.32
Q5    1   1.0782  0.3068  0.4060  11.00000  0.05    0.29
Q6    1   1.0264  0.3341  0.7262  11.00000  0.05    0.28
Q7    1   0.5805  0.1544  0.2796  11.00000  0.05    0.28
Q8    1   0.9745  0.2955  0.4898  11.00000  0.05    0.26
Q9    1   0.7406  0.7665  0.3732  11.00000  0.05    0.26
Q10   1   0.4731  0.1517  0.4730  11.00000  0.05    0.26
;
_shelx_res_checksum              49358
####################################################################### 
# 
# 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_twinned_domain
_database_code_depnum_ccdc_archive 'CCDC 1825188'
_audit_update_record             
;
2018-02-22 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 O4'
_chemical_formula_weight         172.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6186(11)
_cell_length_b                   8.0802(16)
_cell_length_c                   9.6186(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.636(2)
_cell_angle_gamma                90
_cell_volume                     418.40(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1546
_cell_measurement_theta_min      3.353
_cell_measurement_theta_max      26.5065

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             184
_exptl_transmission_factor_min   0.653514
_exptl_transmission_factor_max   0.745559
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.326
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART Breeze'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            870
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.353
_diffrn_reflns_theta_max         27.622
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             870
_reflns_number_gt                690
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1450P)²+0.0875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.76(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         870
_refine_ls_number_parameters     57
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0986
_refine_ls_wR_factor_ref         0.2316
_refine_ls_wR_factor_gt          0.2177
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4375(5) 0.5364(3) 0.6345(3) 0.0459(8) Uani 1 1 d . . . . .
H1 H 0.3011 0.6146 0.5963 0.055 Uiso 1 1 calc R U . . .
C2 C 0.3618(6) 0.3738(4) 0.5564(3) 0.0553(9) Uani 1 1 d . . . . .
H2A H 0.2051 0.3378 0.5697 0.066 Uiso 1 1 calc R U . . .
H2B H 0.4859 0.2904 0.5980 0.066 Uiso 1 1 calc R U . . .
C3 C 0.3349(6) 0.3908(4) 0.3941(3) 0.0592(9) Uani 1 1 d . . . . .
H3A H 0.3032 0.2825 0.3489 0.071 Uiso 1 1 calc R U . . .
H3B H 0.1930 0.4607 0.3499 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4684(5) 0.5184(3) 0.7955(3) 0.0445(8) Uani 1 1 d . . . . .
O1 O 0.2852(4) 0.4472(3) 0.8273(2) 0.0667(9) Uani 1 1 d . . . . .
H1A H 0.3148 0.4414 0.9157 0.100 Uiso 1 1 calc R U . . .
O2 O 0.6511(4) 0.5701(3) 0.88880(19) 0.0656(9) Uani 1 1 d . . . . .

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 0.0568(16) 0.0531(16) 0.0301(14) 0.0016(10) 0.0162(11) -0.0010(11)
C2 0.0738(18) 0.0647(18) 0.0323(15) -0.0034(12) 0.0229(13) -0.0226(14)
C3 0.0748(19) 0.077(2) 0.0278(14) -0.0075(12) 0.0180(12) -0.0294(15)
C4 0.0591(15) 0.0487(14) 0.0299(13) -0.0019(10) 0.0194(12) -0.0054(12)
O1 0.0749(15) 0.1003(18) 0.0305(12) -0.0062(10) 0.0240(10) -0.0290(12)
O2 0.0737(15) 0.0978(17) 0.0269(11) -0.0052(10) 0.0169(10) -0.0296(12)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.503(4) 3_666 ?
C1 C2 1.513(4) . ?
C1 C4 1.515(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.531(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C1 1.503(4) 3_666 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O2 1.227(3) . ?
C4 O1 1.290(3) . ?
O1 H1A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 112.5(2) 3_666 . ?
C3 C1 C4 111.7(2) 3_666 . ?
C2 C1 C4 110.9(2) . . ?
C3 C1 H1 107.1 3_666 . ?
C2 C1 H1 107.1 . . ?
C4 C1 H1 107.1 . . ?
C1 C2 C3 111.1(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C1 C3 C2 112.4(2) 3_666 . ?
C1 C3 H3A 109.1 3_666 . ?
C2 C3 H3A 109.1 . . ?
C1 C3 H3B 109.1 3_666 . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O2 C4 O1 122.4(2) . . ?
O2 C4 C1 122.8(2) . . ?
O1 C4 C1 114.8(2) . . ?
C4 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.225

_shelx_res_file                  
;

    twin5_a.res created by SHELXL-2014/7

TITL twin5_a.res in P2(1)/n
CELL  0.71073   5.6186   8.0802   9.6186   90.000  106.636   90.000
ZERR    2.000   0.0011   0.0016   0.0018    0.000    0.002    0.000
LATT 1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C  H  O
UNIT 16  24  8
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 10
size 0.512 0.401 0.326
TEMP 25.000
WGHT    0.145000    0.087500
EXTI    0.755563
BASF   0.43554
FVAR       1.97841
C1    1    0.437529    0.536446    0.634524    11.00000    0.05678    0.05311 =
         0.03009    0.00164    0.01621   -0.00100
AFIX  13
H1    2    0.301053    0.614573    0.596250    11.00000   -1.20000
AFIX   0
C2    1    0.361819    0.373809    0.556414    11.00000    0.07376    0.06467 =
         0.03235   -0.00336    0.02288   -0.02265
AFIX  23
H2A   2    0.205068    0.337766    0.569651    11.00000   -1.20000
H2B   2    0.485867    0.290353    0.598004    11.00000   -1.20000
AFIX   0
C3    1    0.334880    0.390762    0.394064    11.00000    0.07482    0.07695 =
         0.02779   -0.00747    0.01802   -0.02939
AFIX  23
H3A   2    0.303232    0.282514    0.348934    11.00000   -1.20000
H3B   2    0.193011    0.460656    0.349896    11.00000   -1.20000
AFIX   0
C4    1    0.468412    0.518366    0.795478    11.00000    0.05906    0.04869 =
         0.02986   -0.00186    0.01942   -0.00535
O1    3    0.285202    0.447236    0.827284    11.00000    0.07489    0.10028 =
         0.03054   -0.00623    0.02405   -0.02897
AFIX  83
H1A   2    0.314774    0.441361    0.915713    11.00000   -1.50000
AFIX   0
O2    3    0.651054    0.570092    0.888796    11.00000    0.07366    0.09778 =
         0.02693   -0.00517    0.01694   -0.02957
HKLF 5

REM  twin5_a.res in P2(1)/n
REM R1 =  0.0986 for     690 Fo > 4sig(Fo)  and  0.1098 for all     870 data
REM     57 parameters refined using      0 restraints

END

WGHT      0.1490      0.0826

REM Highest difference peak  0.468,  deepest hole -0.769,  1-sigma level  0.225
Q1    1   0.1733  0.3381  0.3282  11.00000  0.05    0.47
Q2    1   0.7041  0.6140  0.8960  11.00000  0.05    0.46
Q3    1   0.3559  0.3868  0.8403  11.00000  0.05    0.44
Q4    1   0.2237  0.4122  0.8223  11.00000  0.05    0.42
Q5    1   0.3237  0.2857  0.5914  11.00000  0.05    0.40
Q6    1   0.1951  0.3686  0.7970  11.00000  0.05    0.39
Q7    1   0.2500  0.4520  0.5441  11.00000  0.05    0.38
Q8    1   0.1269  0.3881  0.5695  11.00000  0.05    0.34
Q9    1   0.4052  0.2455  0.3653  11.00000  0.05    0.30
Q10   1   0.5367  0.2086  0.4243  11.00000  0.05    0.27
;
_shelx_res_checksum              64888
