# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       iain.oswald@strath.ac.uk
_publ_contact_author_name        'Iain D.H.Oswald'
loop_
_publ_author_name
'Iain D.H.Oswald'
'Andrew Urquhart'

data_1
_database_code_depnum_ccdc_archive 'CCDC 816976'
#TrackingRef '- 1.cif'

_audit_creation_date             11-02-15
_audit_creation_method           CRYSTALS_ver_14.11

_cell_length_a                   9.959(3)
_cell_length_b                   11.667(3)
_cell_length_c                   6.3044(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     732.5(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'I b a m '
_symmetry_space_group_name_Hall  '-I 2 2c'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z+1/2
-x+1/2,-y+1/2,-z+1/2
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
-x+1,y+1,z+1/2
x+1,-y+1,-z+1/2
x+1/2,-y+1/2,z
-x+1/2,y+1/2,-z
x+1,-y+1,z+1/2
-x+1,y+1,-z+1/2
-x,-y,z
x,y,-z
-x+1/2,-y+1/2,z+1/2
x+1/2,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 0.0033 0.0016 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 0.0106 0.0060 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            8

# Given Formula = C3 H4 O2
# Dc = 1.31 Fooo = 304.00 Mu = 1.11 M = 36.03
# Found Formula = C3 H4 O2
# Dc = 1.31 FOOO = 304.00 Mu = 1.11 M = 36.03

_chemical_formula_sum            'C3 H4 O2'
_chemical_formula_moiety         'C3 H4 O2'
_chemical_compound_source        ?
_chemical_formula_weight         72.06

_cell_measurement_reflns_used    400
_cell_measurement_theta_min      5
_cell_measurement_theta_max      18
_cell_measurement_temperature    293

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.111

# Sheldrick geometric approximatio 0.97 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      293
_diffrn_ambient_pressure         400000
_diffrn_reflns_number            1615
_reflns_number_total             201
_diffrn_reflns_av_R_equivalents  0.034
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 201
# Theoretical number of reflections is about 527

_diffrn_reflns_theta_min         5.183
_diffrn_reflns_theta_max         23.268
_diffrn_measured_fraction_theta_max 0.680

_diffrn_reflns_theta_full        17.451
_diffrn_measured_fraction_theta_full 0.763

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.21

# 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>-10.0\s(I)
_refine_ls_number_reflns         201
_refine_ls_number_restraints     31
_refine_ls_number_parameters     34
_oxford_refine_ls_R_factor_ref   0.0761
_refine_ls_wR_factor_ref         0.1187
_refine_ls_goodness_of_fit_ref   1.0324
_refine_ls_shift/su_max          0.0000803
_refine_ls_shift/su_mean         0.0000163

# The values computed from all data
_oxford_reflns_number_all        201
_refine_ls_R_factor_all          0.0761
_refine_ls_wR_factor_all         0.1187

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                113
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.0931

# 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 .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 0.02P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.6663(3) 0.5640(2) 0.500000(7) 0.0825 1.0000 Uani S TU . . . .
O2 O 0.4589(3) 0.6364(2) 0.5000 0.0744 1.0000 Uani S TU . . . .
C1 C 0.5814(6) 0.6502(4) 0.5000 0.0623 1.0000 Uani S TU . . . .
C2 C 0.6462(5) 0.7626(4) 0.500000(7) 0.0800 1.0000 Uani S TU . . . .
C3 C 0.5768(6) 0.8566(5) 0.500000(5) 0.1070 1.0000 Uani S TU . . . .
H1 H 0.6177 0.5039 0.5000 0.1223 1.0000 Uiso RS . . . . .
H2 H 0.7466 0.7681 0.5000 0.1043 1.0000 Uiso RS . . . . .
H3 H 0.6146 0.9332 0.5000 0.1303 1.0000 Uiso RS . . . . .
H4 H 0.4781 0.8538 0.5000 0.1303 1.0000 Uiso RS . . . . .
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
O1 0.052(3) 0.066(2) 0.130(2) 0.0000 0.0000 0.0051(13)
O2 0.047(3) 0.062(2) 0.115(2) 0.0000 0.0000 0.0001(12)
C1 0.047(3) 0.062(3) 0.078(2) 0.0000 0.0000 0.0023(14)
C2 0.059(4) 0.068(3) 0.113(3) 0.0000 0.0000 -0.0075(14)
C3 0.086(6) 0.060(4) 0.176(5) 0.0000 0.0000 -0.007(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1885(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C1 . 1.313(5) yes
O1 . H1 . 0.852 no
O2 . C1 . 1.230(5) yes
C1 . C2 . 1.461(7) yes
C2 . C3 . 1.297(7) yes
C2 . H2 . 1.002 no
C3 . H3 . 0.970 no
C3 . H4 . 0.983 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
C1 . O1 . H1 . 105.3 no
O1 . C1 . O2 . 122.6(5) yes
O1 . C1 . C2 . 113.7(6) yes
O2 . C1 . C2 . 123.7(4) yes
C1 . C2 . C3 . 121.6(6) yes
C1 . C2 . H2 . 119.9 no
C3 . C2 . H2 . 118.5 no
C2 . C3 . H3 . 124.9 no
C2 . C3 . H4 . 120.3 no
H3 . C3 . H4 . 114.8 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/02/11 at 13:41:41
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE O ( 1,X'S) H ( 1,X'S)
RIDE C ( 2,X'S) H ( 2,X'S)
RIDE C ( 3,X'S) H ( 3,X'S) H ( 4,X'S)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/02/11 at 13:41:41
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
REM DELU START (DO NOT REMOVE THIS LINE)
VIBR .0, 0.00200 = O(1) TO C(1)
VIBR .0, 0.00200 = O(2) TO C(1)
VIBR .0, 0.00200 = C(1) TO C(2)
VIBR .0, 0.00500 = O(2) TO O(1)
VIBR .0, 0.00500 = C(2) TO O(1)
VIBR .0, 0.00500 = C(2) TO O(2)
VIBR .0, 0.00200 = C(2) TO C(3)
VIBR .0, 0.00500 = C(3) TO C(1)
REM DELU END (DO NOT REMOVE THIS LINE)
REM THERMSIM START (DO NOT REMOVE THIS LINE)
U(IJ) .0, 0.08000 = O(1) TO C(1)
U(IJ) .0, 0.08000 = O(2) TO C(1)
U(IJ) .0, 0.04000 = C(1) TO C(2)
U(IJ) .0, 0.08000 = C(2) TO C(3)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
END
;

# Attachment '- 2.cif'

data_2
_database_code_depnum_ccdc_archive 'CCDC 816977'
#TrackingRef '- 2.cif'

_audit_creation_date             11-02-15
_audit_creation_method           CRYSTALS_ver_14.11

_cell_length_a                   5.1352(10)
_cell_length_b                   9.802(3)
_cell_length_c                   6.850(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.28(3)
_cell_angle_gamma                90
_cell_volume                     342.0(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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 0.0033 0.0016 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 0.0106 0.0060 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 = C3 H4 O2
# Dc = 1.40 Fooo = 152.00 Mu = 1.19 M = 72.06
# Found Formula = C3 H4 O2
# Dc = 1.40 FOOO = 152.00 Mu = 1.19 M = 72.06

_chemical_formula_sum            'C3 H4 O2'
_chemical_formula_moiety         'C3 H4 O2'
_chemical_compound_source        ?
_chemical_formula_weight         72.06

_cell_measurement_reflns_used    221
_cell_measurement_theta_min      4
_cell_measurement_theta_max      20
_cell_measurement_temperature    293

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             152
_exptl_absorpt_coefficient_mu    0.119

# Sheldrick geometric approximatio 0.96 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      293
_diffrn_ambient_pressure         650000
_diffrn_reflns_number            947
_reflns_number_total             267
_diffrn_reflns_av_R_equivalents  0.052
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 267
# Theoretical number of reflections is about 984

_diffrn_reflns_theta_min         3.648
_diffrn_reflns_theta_max         23.268
_diffrn_measured_fraction_theta_max 0.543

_diffrn_reflns_theta_full        17.916
_diffrn_measured_fraction_theta_full 0.681

_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_reflns_limit_h_min              -5
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              5

_oxford_diffrn_Wilson_B_factor   2.34
_oxford_diffrn_Wilson_scale      0.34

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.31

# 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>-10.0\s(I)
_refine_ls_number_reflns         267
_refine_ls_number_restraints     0
_refine_ls_number_parameters     46
_oxford_refine_ls_R_factor_ref   0.0754
_refine_ls_wR_factor_ref         0.0888
_refine_ls_goodness_of_fit_ref   1.0481
_refine_ls_shift/su_max          0.0000770
_refine_ls_shift/su_mean         0.0000160

# The values computed from all data
_oxford_reflns_number_all        267
_refine_ls_R_factor_all          0.0754
_refine_ls_wR_factor_all         0.0888

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                189
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_gt          0.0808

# 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 .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 0.00P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
O2 O 0.7519(4) 0.5346(2) 0.1642(5) 0.0513 1.0000 Uani . . . . . .
C1 C 0.8047(6) 0.4142(4) 0.1398(8) 0.0420 1.0000 Uani . . . . . .
O1 O 0.6581(5) 0.3342(2) 0.0204(6) 0.0560 1.0000 Uani . . . . . .
C2 C 1.0403(7) 0.3485(3) 0.2423(9) 0.0433 1.0000 Uani . . . . . .
C3 C 1.2167(7) 0.4168(4) 0.3551(9) 0.0515 1.0000 Uani . . . . . .
H2 H 1.0628 0.2556 0.2247 0.0531 1.0000 Uiso R . . . . .
H3 H 1.3673 0.3747 0.4196 0.0620 1.0000 Uiso R . . . . .
H4 H 1.1961 0.5091 0.3731 0.0621 1.0000 Uiso R . . . . .
H1 H 0.5207 0.3764 -0.0340 0.0832 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0540(15) 0.0333(16) 0.062(4) -0.0080(14) -0.0083(17) 0.0031(12)
C1 0.038(2) 0.039(3) 0.049(7) 0.002(2) 0.006(3) -0.0078(18)
O1 0.0469(16) 0.0410(18) 0.074(5) -0.0109(16) -0.013(2) 0.0029(12)
C2 0.037(2) 0.039(2) 0.051(7) 0.005(2) -0.004(3) 0.003(2)
C3 0.044(2) 0.061(3) 0.048(8) 0.010(2) 0.000(3) 0.0092(19)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.12(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
O2 . C1 . 1.227(4) yes
C1 . O1 . 1.302(5) yes
C1 . C2 . 1.468(6) yes
O1 . H1 . 0.861 no
C2 . C3 . 1.299(6) yes
C2 . H2 . 0.927 no
C3 . H3 . 0.937 no
C3 . H4 . 0.921 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
O2 . C1 . O1 . 123.0(4) yes
O2 . C1 . C2 . 122.7(4) yes
O1 . C1 . C2 . 114.3(3) yes
C1 . O1 . H1 . 111.0 no
C1 . C2 . C3 . 121.9(4) yes
C1 . C2 . H2 . 118.5 no
C3 . C2 . H2 . 119.6 no
C2 . C3 . H3 . 121.6 no
C2 . C3 . H4 . 120.2 no
H3 . C3 . H4 . 118.2 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/02/11 at 16:16:44
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE O ( 1,X'S) H ( 1,X'S)
RIDE C ( 2,X'S) H ( 2,X'S)
RIDE C ( 3,X'S) H ( 3,X'S) H ( 4,X'S)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/02/11 at 16:16:44
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;

# Attachment '- 3.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 816978'
#TrackingRef '- 3.cif'

_audit_creation_date             11-02-15
_audit_creation_method           CRYSTALS_ver_14.11

_cell_length_a                   3.8056(3)
_cell_length_b                   10.4842(8)
_cell_length_c                   11.6286(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.468(4)
_cell_angle_gamma                90
_cell_volume                     463.81(6)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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 0.0033 0.0016 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 0.0106 0.0060 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 = C4 H6 O2
# Dc = 1.23 Fooo = 184.00 Mu = 0.99 M = 86.09
# Found Formula = C4 H6 O2
# Dc = 1.23 FOOO = 184.00 Mu = 0.99 M = 86.09

_chemical_formula_sum            'C4 H6 O2'
_chemical_formula_moiety         'C4 H6 O2'
_chemical_compound_source        ?
_chemical_formula_weight         86.09

_cell_measurement_reflns_used    1777
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_temperature    123

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    0.099

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      123
_diffrn_reflns_number            3210
_reflns_number_total             920
_diffrn_reflns_av_R_equivalents  0.013
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 920
# Theoretical number of reflections is about 1914

_diffrn_reflns_theta_min         2.616
_diffrn_reflns_theta_max         26.455
_diffrn_measured_fraction_theta_max 0.959

_diffrn_reflns_theta_full        25.133
_diffrn_measured_fraction_theta_full 0.992

_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   3.36
_oxford_diffrn_Wilson_scale      0.31

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

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.17

# 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>-10.0\s(I)
_refine_ls_number_reflns         920
_refine_ls_number_restraints     0
_refine_ls_number_parameters     55
_oxford_refine_ls_R_factor_ref   0.0399
_refine_ls_wR_factor_ref         0.0870
_refine_ls_goodness_of_fit_ref   0.9771
_refine_ls_shift/su_max          0.0003546
_refine_ls_shift/su_mean         0.0000468

# The values computed from all data
_oxford_reflns_number_all        920
_refine_ls_R_factor_all          0.0399
_refine_ls_wR_factor_all         0.0870

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                748
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_gt          0.0841

# 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 .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.10P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
O2 O 1.0190(2) 0.65767(8) 0.50132(7) 0.0438 1.0000 Uani . . . . . .
C1 C 0.8632(3) 0.64187(11) 0.59207(10) 0.0372 1.0000 Uani . . . . . .
O1 O 0.7854(2) 0.52996(8) 0.63162(7) 0.0479 1.0000 Uani . . . . . .
C2 C 0.7557(3) 0.75240(12) 0.66234(11) 0.0431 1.0000 Uani . . . . . .
C4 C 0.8145(4) 0.87875(13) 0.61190(14) 0.0591 1.0000 Uani . . . . . .
C3 C 0.6186(4) 0.73252(15) 0.76595(12) 0.0562 1.0000 Uani . . . . . .
H5 H 0.7455 0.9460 0.6652 0.0873 1.0000 Uiso R . . . . .
H7 H 1.0637 0.8886 0.5909 0.0897 1.0000 Uiso R . . . . .
H6 H 0.6753 0.8861 0.5409 0.0891 1.0000 Uiso R . . . . .
H3 H 0.5503 0.8025 0.8122 0.0688 1.0000 Uiso R . . . . .
H4 H 0.5854 0.6490 0.7914 0.0692 1.0000 Uiso R . . . . .
H1 H 0.8559 0.4668 0.5868 0.0749 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0504(5) 0.0405(5) 0.0407(5) 0.0022(4) 0.0056(4) 0.0011(4)
C1 0.0333(6) 0.0402(6) 0.0378(6) -0.0002(5) -0.0044(5) 0.0027(4)
O1 0.0594(6) 0.0398(5) 0.0452(5) 0.0016(4) 0.0134(4) 0.0020(4)
C2 0.0342(6) 0.0463(7) 0.0483(7) -0.0110(5) -0.0076(5) 0.0051(5)
C4 0.0545(8) 0.0429(7) 0.0794(10) -0.0118(7) -0.0060(7) 0.0068(6)
C3 0.0490(8) 0.0680(9) 0.0517(8) -0.0209(7) 0.0010(6) 0.0049(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.92(2)
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
O2 . C1 . 1.2347(13) yes
C1 . O1 . 1.2972(14) yes
C1 . C2 . 1.4816(16) yes
O1 . H1 . 0.889 no
C2 . C4 . 1.4682(19) yes
C2 . C3 . 1.3414(19) yes
C4 . H5 . 0.979 no
C4 . H7 . 0.991 no
C4 . H6 . 0.972 no
C3 . H3 . 0.950 no
C3 . H4 . 0.934 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
O2 . C1 . O1 . 122.91(10) yes
O2 . C1 . C2 . 120.79(10) yes
O1 . C1 . C2 . 116.30(10) yes
C1 . O1 . H1 . 113.0 no
C1 . C2 . C4 . 115.99(12) yes
C1 . C2 . C3 . 119.55(12) yes
C4 . C2 . C3 . 124.45(12) yes
C2 . C4 . H5 . 110.5 no
C2 . C4 . H7 . 110.4 no
H5 . C4 . H7 . 110.8 no
C2 . C4 . H6 . 109.0 no
H5 . C4 . H6 . 109.3 no
H7 . C4 . H6 . 106.7 no
C2 . C3 . H3 . 120.5 no
C2 . C3 . H4 . 119.3 no
H3 . C3 . H4 . 120.2 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/02/11 at 13:51:45
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE O ( 1,X'S) H ( 1,X'S)
RIDE C ( 4,X'S) H ( 5,X'S) H ( 7,X'S) H ( 6,X'S)
RIDE C ( 3,X'S) H ( 3,X'S) H ( 4,X'S)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/02/11 at 13:51:45
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;

# Attachment '- 4.cif'

data_4
_database_code_depnum_ccdc_archive 'CCDC 816979'
#TrackingRef '- 4.cif'

_audit_creation_date             11-02-15
_audit_creation_method           CRYSTALS_ver_14.11

_cell_length_a                   3.8808(11)
_cell_length_b                   10.616(6)
_cell_length_c                   11.718(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.24(2)
_cell_angle_gamma                90
_cell_volume                     482.6(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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 0.0033 0.0016 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 0.0106 0.0060 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 = C4 H6 O2
# Dc = 1.18 Fooo = 184.00 Mu = 0.95 M = 86.09
# Found Formula = C4 H6 O2
# Dc = 1.18 FOOO = 184.00 Mu = 0.95 M = 86.09

_chemical_formula_sum            'C4 H6 O2'
_chemical_formula_moiety         'C4 H6 O2'
_chemical_compound_source        ?
_chemical_formula_weight         86.09

_cell_measurement_reflns_used    275
_cell_measurement_theta_min      3
_cell_measurement_theta_max      19
_cell_measurement_temperature    293

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    0.095

# Sheldrick geometric approximatio 0.97 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_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      293
_diffrn_ambient_pressure         300000
_diffrn_reflns_number            1966
_reflns_number_total             350
_diffrn_reflns_av_R_equivalents  0.034
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 350
# Theoretical number of reflections is about 1388

_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         23.263
_diffrn_measured_fraction_theta_max 0.501

_diffrn_reflns_theta_full        17.447
_diffrn_measured_fraction_theta_full 0.618

_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   4.95
_oxford_diffrn_Wilson_scale      2.09

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

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.27

# 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>-10.0\s(I)
_refine_ls_number_reflns         350
_refine_ls_number_restraints     28
_refine_ls_number_parameters     55
_oxford_refine_ls_R_factor_ref   0.1155
_refine_ls_wR_factor_ref         0.1354
_refine_ls_goodness_of_fit_ref   1.0836
_refine_ls_shift/su_max          0.0000630
_refine_ls_shift/su_mean         0.0000145

# The values computed from all data
_oxford_reflns_number_all        350
_refine_ls_R_factor_all          0.1155
_refine_ls_wR_factor_all         0.1354

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                197
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_gt          0.1143

# 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 .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.39P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Sheldrick, G. M. (2008). Acta Cryst A64, 112-122.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

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

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.8513(17) 0.8627(9) 0.4052(6) 0.0924 1.0000 Uani D U . . . .
C2 C 0.743(2) 0.7520(11) 0.3370(7) 0.1125 1.0000 Uani D U . . . .
C4 C 0.797(3) 0.6273(11) 0.3868(8) 0.1502 1.0000 Uani D U . . . .
C3 C 0.6048(17) 0.7745(11) 0.2317(6) 0.1455 1.0000 Uani D U . . . .
O2 O 0.7928(14) 0.9710(7) 0.3699(4) 0.1124 1.0000 Uani D . . . . .
O1 O 1.0072(12) 0.8399(6) 0.4996(4) 0.1179 1.0000 Uani D . . . . .
H5 H 0.7260 0.5665 0.3283 0.2376 1.0000 Uiso R . . . . .
H7 H 1.0295 0.6129 0.4098 0.2382 1.0000 Uiso R . . . . .
H6 H 0.6464 0.6146 0.4533 0.2386 1.0000 Uiso R . . . . .
H4 H 0.5821 0.8586 0.2098 0.1674 1.0000 Uiso R . . . . .
H3 H 0.5335 0.7073 0.1892 0.1670 1.0000 Uiso R . . . . .
H1 H 1.0753 0.9006 0.5415 0.1728 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.082(4) 0.117(9) 0.078(5) -0.003(4) -0.008(4) -0.011(6)
C2 0.088(4) 0.135(10) 0.115(5) -0.036(4) 0.008(4) -0.009(7)
C4 0.143(6) 0.123(10) 0.185(8) -0.031(6) 0.010(6) -0.017(9)
C3 0.136(6) 0.185(13) 0.114(5) -0.055(5) -0.015(4) -0.021(7)
O2 0.148(4) 0.083(8) 0.105(4) 0.013(3) -0.030(3) 0.001(4)
O1 0.133(3) 0.113(9) 0.107(4) -0.002(3) -0.025(3) -0.006(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.066(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
C1 . C2 . 1.478(14) yes
C1 . O2 . 1.241(8) yes
C1 . O1 . 1.273(6) yes
C2 . C4 . 1.459(9) yes
C2 . C3 . 1.356(7) yes
C4 . H5 . 0.976 no
C4 . H7 . 0.950 no
C4 . H6 . 0.992 no
C3 . H4 . 0.933 no
C3 . H3 . 0.909 no
O1 . H1 . 0.849 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 . O2 . 120.6(7) yes
C2 . C1 . O1 . 116.3(8) yes
O2 . C1 . O1 . 123.1(8) yes
C1 . C2 . C4 . 118.0(9) yes
C1 . C2 . C3 . 117.0(9) yes
C4 . C2 . C3 . 125.0(9) yes
C2 . C4 . H5 . 106.5 no
C2 . C4 . H7 . 112.8 no
H5 . C4 . H7 . 110.1 no
C2 . C4 . H6 . 110.8 no
H5 . C4 . H6 . 107.4 no
H7 . C4 . H6 . 109.1 no
C2 . C3 . H4 . 116.9 no
C2 . C3 . H3 . 118.0 no
H4 . C3 . H3 . 125.0 no
C1 . O1 . H1 . 119.6 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/02/11 at 14:38:32
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE C ( 4,X'S) H ( 5,X'S) H ( 7,X'S) H ( 6,X'S)
RIDE C ( 3,X'S) H ( 4,X'S) H ( 3,X'S)
RIDE O ( 1,X'S) H ( 1,X'S)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/02/11 at 14:38:32
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
REM DELU START (DO NOT REMOVE THIS LINE)
VIBR .0, 0.00100 = C(1) TO C(2)
VIBR .0, 0.00100 = C(2) TO C(3)
VIBR .0, 0.00100 = C(2) TO C(4)
VIBR .0, 0.00300 = C(3) TO C(1)
VIBR .0, 0.00300 = C(4) TO C(1)
VIBR .0, 0.00300 = C(4) TO C(3)
VIBR .0, 0.00100 = C(4) TO O(5)
VIBR .0, 0.00100 = C(4) TO O(6)
VIBR .0, 0.00300 = O(5) TO C(2)
VIBR .0, 0.00300 = O(6) TO C(2)
VIBR .0, 0.00300 = O(6) TO O(5)
REM DELU END (DO NOT REMOVE THIS LINE)
REM THERMSIM START (DO NOT REMOVE THIS LINE)
U(IJ) .0, 0.04000 = C(1) TO C(2)
U(IJ) .0, 0.04000 = C(2) TO C(3)
U(IJ) .0, 0.02000 = C(2) TO C(4)
U(IJ) .0, 0.04000 = C(4) TO O(5)
U(IJ) .0, 0.04000 = C(4) TO O(6)
REM THERMSIM END (DO NOT REMOVE THIS LINE)
DISTANCE 1.310000 , 0.010000 = C(1) TO O(1)
DISTANCE 1.230000 , 0.010000 = C(1) TO O(2)
DISTANCE 1.340000 , 0.010000 = C(2) TO C(3)
DISTANCE 1.470000 , 0.010000 = C(2) TO C(4)
END
;

# Attachment '- 5.cif'

data_5
_database_code_depnum_ccdc_archive 'CCDC 816980'
#TrackingRef '- 5.cif'

_audit_creation_date             11-02-15
_audit_creation_method           CRYSTALS_ver_14.11

_cell_length_a                   3.7643(13)
_cell_length_b                   13.501(6)
_cell_length_c                   8.308(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.22(3)
_cell_angle_gamma                90
_cell_volume                     414.1(3)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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 0.0033 0.0016 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 0.0106 0.0060 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 = C4 H6 O2
# Dc = 1.38 Fooo = 184.00 Mu = 1.11 M = 86.09
# Found Formula = C4 H6 O2
# Dc = 1.38 FOOO = 184.00 Mu = 1.11 M = 86.09

_chemical_formula_sum            'C4 H6 O2'
_chemical_formula_moiety         'C4 H6 O2'
_chemical_compound_source        ?
_chemical_formula_weight         86.09

_cell_measurement_reflns_used    130
_cell_measurement_theta_min      3
_cell_measurement_theta_max      17
_cell_measurement_temperature    293

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.300

_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    0.111

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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      293
_diffrn_ambient_pressure         1500000
_diffrn_reflns_number            602
_reflns_number_total             297
_diffrn_reflns_av_R_equivalents  0.053
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 297
# Theoretical number of reflections is about 1176

_diffrn_reflns_theta_min         2.920
_diffrn_reflns_theta_max         23.158
_diffrn_measured_fraction_theta_max 0.506

_diffrn_reflns_theta_full        17.368
_diffrn_measured_fraction_theta_full 0.673

_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   2.65
_oxford_diffrn_Wilson_scale      0.32

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

_refine_diff_density_min         -0.34
_refine_diff_density_max         0.32

# 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>-10.0\s(I)
_refine_ls_number_reflns         297
_refine_ls_number_restraints     0
_refine_ls_number_parameters     55
_oxford_refine_ls_R_factor_ref   0.0854
_refine_ls_wR_factor_ref         0.1118
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_shift/su_max          0.0000528
_refine_ls_shift/su_mean         0.0000112

# The values computed from all data
_oxford_reflns_number_all        297
_refine_ls_R_factor_all          0.0854
_refine_ls_wR_factor_all         0.1118

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                198
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.0978

# 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 .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.32P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Bruker Analytical X-ray Systems, Inc., 2006. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;

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

# Replace last . with number of unfound hydrogen atomsattached 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
O2 O 0.9591(10) 0.3830(2) 0.9470(5) 0.0467 1.0000 Uani . . . . . .
C1 C 0.7399(15) 0.4173(5) 0.8306(8) 0.0362 1.0000 Uani . . . . . .
O1 O 0.6724(11) 0.5118(3) 0.8121(5) 0.0619 1.0000 Uani . . . . . .
C2 C 0.5372(14) 0.3531(4) 0.6998(8) 0.0361 1.0000 Uani . . . . . .
C3 C 0.3024(14) 0.3927(4) 0.5778(8) 0.0525 1.0000 Uani . . . . . .
C4 C 0.6148(14) 0.2464(4) 0.7190(8) 0.0509 1.0000 Uani . . . . . .
H5 H 0.4769 0.2095 0.6296 0.0786 1.0000 Uiso R . . . . .
H6 H 0.5478 0.2227 0.8174 0.0792 1.0000 Uiso R . . . . .
H7 H 0.8686 0.2327 0.7250 0.0790 1.0000 Uiso R . . . . .
H3 H 0.1992 0.3549 0.4838 0.0619 1.0000 Uiso R . . . . .
H4 H 0.2389 0.4597 0.5857 0.0622 1.0000 Uiso R . . . . .
H1 H 0.7875 0.5527 0.8811 0.0919 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.051(3) 0.045(3) 0.038(4) 0.0041(18) -0.005(2) 0.001(2)
C1 0.038(4) 0.037(5) 0.038(6) -0.001(3) 0.019(4) -0.003(3)
O1 0.080(3) 0.041(4) 0.054(5) -0.0053(17) -0.015(3) -0.002(2)
C2 0.032(3) 0.055(5) 0.024(6) -0.002(3) 0.012(3) -0.004(3)
C3 0.045(4) 0.078(5) 0.033(6) -0.008(3) 0.004(4) 0.003(3)
C4 0.046(4) 0.049(6) 0.057(7) -0.012(3) 0.010(4) -0.011(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.10(6)
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
O2 . C1 . 1.232(6) yes
C1 . O1 . 1.305(6) yes
C1 . C2 . 1.481(7) yes
O1 . H1 . 0.851 no
C2 . C3 . 1.321(6) yes
C2 . C4 . 1.472(6) yes
C3 . H3 . 0.950 no
C3 . H4 . 0.940 no
C4 . H5 . 0.960 no
C4 . H6 . 0.956 no
C4 . H7 . 0.965 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
O2 . C1 . O1 . 123.0(5) yes
O2 . C1 . C2 . 121.8(6) yes
O1 . C1 . C2 . 115.2(5) yes
C1 . O1 . H1 . 119.5 no
C1 . C2 . C3 . 119.9(6) yes
C1 . C2 . C4 . 115.5(5) yes
C3 . C2 . C4 . 124.6(5) yes
C2 . C3 . H3 . 121.2 no
C2 . C3 . H4 . 118.5 no
H3 . C3 . H4 . 120.4 no
C2 . C4 . H5 . 111.0 no
C2 . C4 . H6 . 109.9 no
H5 . C4 . H6 . 107.2 no
C2 . C4 . H7 . 111.5 no
H5 . C4 . H7 . 108.7 no
H6 . C4 . H7 . 108.3 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 15/02/11 at 14:48:53
#
#LIST 12
BLOCK SCALE X'S, U'S
RIDE O ( 1,X'S) H ( 1,X'S)
RIDE C ( 3,X'S) H ( 3,X'S) H ( 4,X'S)
RIDE C ( 4,X'S) H ( 5,X'S) H ( 6,X'S) H ( 7,X'S)
END
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 15/02/11 at 14:48:53
#
#LIST 16
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;