# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 1034375'
_audit_update_record             
;
2014-11-16 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        '4-methylbenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 O2'
_chemical_formula_weight         136.14

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.308(6)
_cell_length_b                   7.452(6)
_cell_length_c                   7.833(7)
_cell_angle_alpha                96.059(14)
_cell_angle_beta                 108.374(13)
_cell_angle_gamma                117.853(14)
_cell_volume                     341.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    909
_cell_measurement_theta_min      2.8737
_cell_measurement_theta_max      26.1223

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7084
_exptl_absorpt_correction_T_max  0.9484
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            1358
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         26.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1358
_reflns_number_gt                919
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1069P)²+0.0098P] 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         1358
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1514
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.6855(4) 0.3236(4) 0.3635(3) 0.0184(6) Uani 1 1 d . . . . .
C2 C 0.7054(4) 0.1469(4) 0.3300(3) 0.0221(6) Uani 1 1 d . . . . .
H2 H 0.6695 0.0753 0.2055 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7781(4) 0.0765(4) 0.4804(3) 0.0245(6) Uani 1 1 d . . . . .
H3 H 0.7904 -0.0443 0.4573 0.029 Uiso 1 1 calc R U . . .
C4 C 0.8331(4) 0.1806(4) 0.6642(3) 0.0227(6) Uani 1 1 d . . . . .
C5 C 0.8118(4) 0.3561(4) 0.6954(3) 0.0240(6) Uani 1 1 d . . . . .
H5 H 0.8477 0.4275 0.8199 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7387(4) 0.4287(4) 0.5467(3) 0.0204(6) Uani 1 1 d . . . . .
H6 H 0.7253 0.5488 0.5699 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6080(4) 0.4021(4) 0.2061(3) 0.0188(6) Uani 1 1 d . . . . .
C8 C 0.9136(4) 0.1040(5) 0.8279(4) 0.0301(7) Uani 1 1 d . . . . .
H8A H 1.0772 0.2030 0.9030 0.045 Uiso 1 1 calc R U . . .
H8B H 0.8838 -0.0380 0.7790 0.045 Uiso 1 1 calc R U . . .
H8C H 0.8317 0.0976 0.9072 0.045 Uiso 1 1 calc R U . . .
O1 O 0.5724(3) 0.3044(3) 0.0392(2) 0.0277(5) Uani 1 1 d . . . . .
H1 H 0.5292 0.3595 -0.0402 0.042 Uiso 1 1 calc R U . . .
O2 O 0.5775(3) 0.5525(3) 0.2334(2) 0.0262(5) 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 0.0169(12) 0.0242(16) 0.0147(12) 0.0082(9) 0.0052(9) 0.0116(12)
C2 0.0232(13) 0.0250(16) 0.0186(12) 0.0062(10) 0.0068(10) 0.0146(12)
C3 0.0234(13) 0.0247(16) 0.0263(13) 0.0097(11) 0.0071(11) 0.0150(13)
C4 0.0183(13) 0.0279(17) 0.0213(13) 0.0133(11) 0.0070(10) 0.0112(13)
C5 0.0247(13) 0.0351(17) 0.0138(11) 0.0088(10) 0.0069(10) 0.0174(13)
C6 0.0219(12) 0.0241(15) 0.0175(12) 0.0071(10) 0.0072(10) 0.0142(12)
C7 0.0185(12) 0.0243(16) 0.0131(11) 0.0059(9) 0.0047(9) 0.0121(12)
C8 0.0285(15) 0.038(2) 0.0220(13) 0.0143(12) 0.0055(11) 0.0181(15)
O1 0.0401(11) 0.0341(12) 0.0120(9) 0.0086(7) 0.0069(8) 0.0240(10)
O2 0.0360(11) 0.0333(12) 0.0192(9) 0.0110(7) 0.0106(8) 0.0256(10)

_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 C6 1.396(3) . ?
C1 C2 1.398(4) . ?
C1 C7 1.485(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 C8 1.519(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.251(3) . ?
C7 O1 1.309(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 H1 0.8400 . ?

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
C6 C1 C2 120.1(2) . . ?
C6 C1 C7 119.2(2) . . ?
C2 C1 C7 120.8(2) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 C8 120.4(2) . . ?
C3 C4 C8 120.9(2) . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O2 C7 O1 122.53(19) . . ?
O2 C7 C1 121.1(2) . . ?
O1 C7 C1 116.4(2) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 O1 H1 109.5 . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.065

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL twin4_a.res in P-1
CELL  0.71073   7.3077   7.4516   7.8332   96.059  108.374  117.853
ZERR    2.000   0.0061   0.0063   0.0066    0.014    0.013    0.014
LATT 1
SFAC C  H  O
UNIT 16  16  4
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 5
TEMP -173.000
MERG 0
WGHT    0.106900    0.009800
BASF   0.13684
FVAR       1.26530
C1    1    0.685531    0.323644    0.363545    11.00000    0.01685    0.02417 =
         0.01468    0.00823    0.00517    0.01156
C2    1    0.705370    0.146937    0.330008    11.00000    0.02324    0.02505 =
         0.01862    0.00619    0.00685    0.01455
AFIX  43
H2    2    0.669515    0.075325    0.205537    11.00000   -1.20000
AFIX   0
C3    1    0.778089    0.076507    0.480352    11.00000    0.02344    0.02465 =
         0.02633    0.00966    0.00708    0.01502
AFIX  43
H3    2    0.790364   -0.044303    0.457250    11.00000   -1.20000
AFIX   0
C4    1    0.833131    0.180554    0.664186    11.00000    0.01826    0.02787 =
         0.02131    0.01327    0.00702    0.01122
C5    1    0.811824    0.356096    0.695383    11.00000    0.02470    0.03511 =
         0.01381    0.00884    0.00694    0.01743
AFIX  43
H5    2    0.847654    0.427455    0.819933    11.00000   -1.20000
AFIX   0
C6    1    0.738749    0.428730    0.546719    11.00000    0.02186    0.02409 =
         0.01745    0.00708    0.00718    0.01420
AFIX  43
H6    2    0.725283    0.548805    0.569913    11.00000   -1.20000
AFIX   0
C7    1    0.607988    0.402100    0.206076    11.00000    0.01850    0.02434 =
         0.01310    0.00590    0.00466    0.01209
C8    1    0.913600    0.104016    0.827882    11.00000    0.02851    0.03775 =
         0.02200    0.01425    0.00552    0.01811
AFIX 137
H8A   2    1.077178    0.203020    0.903042    11.00000   -1.50000
H8B   2    0.883795   -0.037994    0.778989    11.00000   -1.50000
H8C   2    0.831738    0.097646    0.907218    11.00000   -1.50000
AFIX   0
O1    3    0.572415    0.304449    0.039199    11.00000    0.04008    0.03408 =
         0.01203    0.00861    0.00693    0.02399
AFIX 147
H1    2    0.529167    0.359471   -0.040178    11.00000   -1.50000
AFIX   0
O2    3    0.577499    0.552530    0.233447    11.00000    0.03605    0.03334 =
         0.01917    0.01099    0.01061    0.02557
HKLF 5

REM  twin4_a.res in P-1
REM R1 =  0.0602 for     919 Fo > 4sig(Fo)  and  0.0949 for all    1358 data
REM     94 parameters refined using      0 restraints

END

WGHT      0.1069      0.0111

REM Highest difference peak  0.337,  deepest hole -0.234,  1-sigma level  0.065
Q1    1   0.6067  0.1799  0.3252  11.00000  0.05    0.34
Q2    1   0.7610  0.2857  0.3399  11.00000  0.05    0.31
Q3    1   0.7428  0.2030  0.6648  11.00000  0.05    0.28
Q4    1   0.6662  0.5531  0.2029  11.00000  0.05    0.25
Q5    1   1.0436  0.2410  0.9482  11.00000  0.05    0.25
;
_shelx_res_checksum              49003

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_mo_141114_0m
_database_code_depnum_ccdc_archive 'CCDC 1034687'
_audit_update_record             
;
2014-11-18 deposited with the CCDC.	2019-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'diethyl terephthalate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23

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'
O O 0.0106 0.0060 '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'

_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                   4.206(2)
_cell_length_b                   15.399(9)
_cell_length_c                   9.109(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.854(10)
_cell_angle_gamma                90
_cell_volume                     589.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    218
_cell_measurement_theta_min      2.6003
_cell_measurement_theta_max      22.8073

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8135
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            4463
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1173
_reflns_number_gt                659
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.1292P] 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         1173
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.3577(6) 0.57033(15) 0.9314(3) 0.0661(7) Uani 1 1 d . . . . .
H1 H 0.2611 0.6178 0.8845 0.079 Uiso 1 1 calc R U . . .
C2 C 0.5137(6) 0.50983(15) 0.8508(3) 0.0646(7) Uani 1 1 d . . . . .
H2 H 0.5229 0.5168 0.7497 0.078 Uiso 1 1 calc R U . . .
C3 C 0.6566(5) 0.43893(14) 0.9183(2) 0.0562(6) Uani 1 1 d . . . . .
C4 C 0.8298(6) 0.37218(15) 0.8359(3) 0.0630(7) Uani 1 1 d . . . . .
C5 C 0.9883(7) 0.32820(17) 0.6012(3) 0.0777(8) Uani 1 1 d . . . . .
H5A H 0.8777 0.2729 0.5988 0.093 Uiso 1 1 calc R U . . .
H5B H 1.2048 0.3188 0.6397 0.093 Uiso 1 1 calc R U . . .
C6 C 0.9889(9) 0.3656(2) 0.4530(3) 0.1101(12) Uani 1 1 d . . . . .
H6A H 0.7745 0.3788 0.4193 0.165 Uiso 1 1 calc R U . . .
H6B H 1.0789 0.3246 0.3874 0.165 Uiso 1 1 calc R U . . .
H6C H 1.1136 0.4178 0.4555 0.165 Uiso 1 1 calc R U . . .
O1 O 0.9563(5) 0.31005(12) 0.8914(2) 0.0896(7) Uani 1 1 d . . . . .
O2 O 0.8272(4) 0.38939(10) 0.69301(18) 0.0720(6) 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 0.0729(19) 0.0568(14) 0.0681(16) 0.0141(12) -0.0015(13) 0.0022(12)
C2 0.0717(18) 0.0649(15) 0.0570(13) 0.0119(12) 0.0005(12) -0.0036(12)
C3 0.0537(15) 0.0535(13) 0.0610(14) 0.0065(10) -0.0022(11) -0.0096(10)
C4 0.0592(16) 0.0576(14) 0.0716(17) 0.0081(12) -0.0018(13) -0.0078(12)
C5 0.078(2) 0.0693(16) 0.0858(19) -0.0093(14) 0.0011(15) 0.0105(14)
C6 0.145(3) 0.097(2) 0.091(2) 0.0037(18) 0.036(2) 0.031(2)
O1 0.1065(17) 0.0695(11) 0.0925(13) 0.0157(10) 0.0019(11) 0.0192(11)
O2 0.0804(13) 0.0679(11) 0.0676(11) -0.0003(8) 0.0037(9) 0.0103(9)

_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 C2 1.374(3) . ?
C1 C3 1.380(3) 3_667 ?
C1 H1 0.9300 . ?
C2 C3 1.376(3) . ?
C2 H2 0.9300 . ?
C3 C1 1.380(3) 3_667 ?
C3 C4 1.485(3) . ?
C4 O1 1.194(3) . ?
C4 O2 1.328(3) . ?
C5 O2 1.450(3) . ?
C5 C6 1.467(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
C2 C1 C3 120.4(2) . 3_667 ?
C2 C1 H1 119.8 . . ?
C3 C1 H1 119.8 3_667 . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C1 119.0(2) . 3_667 ?
C2 C3 C4 122.5(2) . . ?
C1 C3 C4 118.5(2) 3_667 . ?
O1 C4 O2 123.8(2) . . ?
O1 C4 C3 124.0(2) . . ?
O2 C4 C3 112.2(2) . . ?
O2 C5 C6 107.3(2) . . ?
O2 C5 H5A 110.3 . . ?
C6 C5 H5A 110.3 . . ?
O2 C5 H5B 110.3 . . ?
C6 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 O2 C5 117.0(2) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL mo_141114_0m.res in P2(1)/n
CELL  0.71073   4.2061  15.3985   9.1091   90.000   92.854   90.000
ZERR    2.000   0.0024   0.0087   0.0051    0.000    0.010    0.000
LATT 1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C  O  H
UNIT 24  8  28
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 5
TEMP 23.000
WGHT    0.063900    0.129200
FVAR       1.27070
C1    1    0.357665    0.570332    0.931445    11.00000    0.07291    0.05679 =
         0.06812    0.01407   -0.00151    0.00219
AFIX  43
H1    3    0.261074    0.617817    0.884550    11.00000   -1.20000
AFIX   0
C2    1    0.513720    0.509826    0.850805    11.00000    0.07174    0.06492 =
         0.05698    0.01188    0.00051   -0.00358
AFIX  43
H2    3    0.522913    0.516816    0.749695    11.00000   -1.20000
AFIX   0
C3    1    0.656619    0.438933    0.918339    11.00000    0.05371    0.05348 =
         0.06101    0.00652   -0.00218   -0.00957
C4    1    0.829834    0.372179    0.835867    11.00000    0.05924    0.05762 =
         0.07161    0.00814   -0.00178   -0.00784
C5    1    0.988317    0.328197    0.601214    11.00000    0.07763    0.06934 =
         0.08579   -0.00934    0.00108    0.01050
AFIX  23
H5A   3    0.877716    0.272900    0.598792    11.00000   -1.20000
H5B   3    1.204798    0.318792    0.639651    11.00000   -1.20000
AFIX   0
C6    1    0.988860    0.365580    0.453043    11.00000    0.14543    0.09713 =
         0.09083    0.00371    0.03625    0.03070
AFIX 137
H6A   3    0.774459    0.378798    0.419285    11.00000   -1.50000
H6B   3    1.078878    0.324582    0.387436    11.00000   -1.50000
H6C   3    1.113598    0.417816    0.455476    11.00000   -1.50000
AFIX   0
O1    2    0.956270    0.310053    0.891360    11.00000    0.10651    0.06954 =
         0.09251    0.01566    0.00188    0.01918
O2    2    0.827194    0.389387    0.693006    11.00000    0.08043    0.06791 =
         0.06762   -0.00027    0.00365    0.01029
HKLF 4

REM  mo_141114_0m.res in P2(1)/n
REM R1 =  0.0536 for     659 Fo > 4sig(Fo)  and  0.1046 for all    1173 data
REM     74 parameters refined using      0 restraints

END

WGHT      0.0638      0.1293

REM Highest difference peak  0.149,  deepest hole -0.144,  1-sigma level  0.034
Q1    1   0.9835  0.4342  0.4154  11.00000  0.05    0.15
Q2    1   1.2693  0.4303  0.5206  11.00000  0.05    0.13
Q3    1   1.1054  0.2711  0.6654  11.00000  0.05    0.12
Q4    1   0.7468  0.3049  0.8395  11.00000  0.05    0.10
Q5    1   0.0835  0.6099  0.8726  11.00000  0.05    0.09
;
_shelx_res_checksum              22976

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane-ethylacetate'
