# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_mrsgb313
_audit_creation_date             2013-02-11
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
3,6-dipropargyloxymethyl-1,4-dioxane-2,5-dione
_chemical_formula_moiety         'C6 H6 O3'
_chemical_formula_sum            'C12 H12 O6'
_chemical_formula_weight         126.11
_chemical_melting_point          125-128
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.6482(12)
_cell_length_b                   7.4766(11)
_cell_length_c                   10.4304(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.535(6)
_cell_angle_gamma                90.00
_cell_volume                     582.22(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3389
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      30.47
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0870 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8928.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             264
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromenthane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 0.5° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5453
_diffrn_reflns_theta_full        68.18
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_min         30.47
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                786
_reflns_number_total             862
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX2 (BRUKER, V2012.10-0, 2012)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.269
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0226P)²+0.3250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, {H4A,H4B} of C4, H1 of C1, {H3A,H3B} of C3
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c :
 C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.87495(17) 0.12537(19) 0.43223(12) 0.0249(4) Uani 1 1 d . . .
O2 O 1.1474(2) 0.0217(2) 0.75116(13) 0.0315(5) Uani 1 1 d . . .
O3 O 0.71730(17) -0.05491(17) 0.61568(12) 0.0226(4) Uani 1 1 d . . .
C1 C 0.9375(2) 0.1422(2) 0.57268(16) 0.0201(5) Uani 1 1 d . . .
H1 H 0.9881 0.2651 0.5916 0.024 Uiso 1 1 calc R . .
C2 C 1.0792(2) 0.0089(2) 0.63628(18) 0.0213(5) Uani 1 1 d . . .
C3 C 0.7774(2) 0.1246(2) 0.63553(16) 0.0209(5) Uani 1 1 d . . .
H3A H 0.8122 0.1518 0.7306 0.025 Uiso 1 1 calc R . .
H3B H 0.6814 0.2083 0.5941 0.025 Uiso 1 1 calc R . .
C4 C 0.5762(2) -0.0929(3) 0.68092(18) 0.0262(5) Uani 1 1 d . . .
H4A H 0.5269 -0.2130 0.6542 0.031 Uiso 1 1 calc R . .
H4B H 0.4788 -0.0046 0.6533 0.031 Uiso 1 1 calc R . .
C5 C 0.6363(2) -0.0875(3) 0.82424(18) 0.0237(5) Uani 1 1 d . . .
C6 C 0.6880(3) -0.0813(3) 0.94064(19) 0.0295(5) Uani 1 1 d . . .
H6 H 0.7291 -0.0763 1.0333 0.035 Uiso 1 1 calc 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
O1 0.0252(7) 0.0339(8) 0.0153(6) 0.0083(5) 0.0039(5) 0.0095(5)
O2 0.0344(8) 0.0394(9) 0.0169(7) 0.0026(5) -0.0031(5) 0.0015(6)
O3 0.0259(7) 0.0233(7) 0.0201(6) -0.0053(5) 0.0086(5) -0.0053(5)
C1 0.0228(9) 0.0216(9) 0.0152(8) 0.0025(6) 0.0025(6) -0.0014(6)
C2 0.0181(8) 0.0273(10) 0.0179(8) 0.0054(7) 0.0024(6) -0.0033(7)
C3 0.0247(9) 0.0201(9) 0.0183(8) -0.0028(6) 0.0058(6) -0.0006(6)
C4 0.0202(9) 0.0367(11) 0.0217(9) -0.0013(7) 0.0044(7) -0.0065(7)
C5 0.0220(9) 0.0258(9) 0.0255(10) 0.0029(7) 0.0096(7) -0.0012(7)
C6 0.0340(10) 0.0341(11) 0.0211(10) 0.0016(7) 0.0077(7) 0.0007(8)

_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
O1 C1 1.445(2) . ?
O1 C2 1.323(3) 3_756 ?
O2 C2 1.202(3) . ?
O3 C3 1.419(2) . ?
O3 C4 1.424(2) . ?
C1 C2 1.515(3) . ?
C1 C3 1.515(2) . ?
C2 O1 1.323(3) 3_756 ?
C4 C5 1.466(3) . ?
C5 C6 1.193(3) . ?

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 O1 C1 123.07(14) 3_756 . ?
C3 O3 C4 111.96(14) . . ?
O1 C1 C2 115.76(15) . . ?
O1 C1 C3 108.08(13) . . ?
C3 C1 C2 108.77(14) . . ?
O1 C2 C1 120.73(16) 3_756 . ?
O2 C2 O1 119.36(17) . 3_756 ?
O2 C2 C1 119.88(17) . . ?
O3 C3 C1 106.61(14) . . ?
O3 C4 C5 112.29(15) . . ?
C6 C5 C4 178.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O1 -7.4(2) . . . 3_756 ?
O1 C1 C2 O2 174.76(16) . . . . ?
O1 C1 C3 O3 67.78(17) . . . . ?
O3 C4 C5 C6 19(10) . . . . ?
C2 O1 C1 C2 7.6(3) 3_756 . . . ?
C2 O1 C1 C3 -114.65(17) 3_756 . . . ?
C2 C1 C3 O3 -58.65(18) . . . . ?
C3 O3 C4 C5 -66.9(2) . . . . ?
C3 C1 C2 O1 114.48(17) . . . 3_756 ?
C3 C1 C2 O2 -63.4(2) . . . . ?
C4 O3 C3 C1 174.74(14) . . . . ?

_contact_Crystallographer_email  staples@chemistry.msu.com
_contact_Crystallographer_name   'Richard Staples'

_shelx_res_file                  
;
TITL mrsgb313 in P2(1)/c
CELL 1.54178 7.6482 7.4766 10.4304 90 102.535 90
ZERR 4 0.0012 0.0011 0.0016 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H O
UNIT 24 24 12


L.S. 12
PLAN  -4 0 0
SIZE 0.1 0.14 0.23
TEMP -100
HTAB 
WPDB -1
CONF 
WPDB -1
fmap 2
acta 
REM <HKL>E:/mrsgb313/work/mrsgb313.hkl</HKL>
WGHT 0.0226 0.325
FVAR 0.85121

O1    3     0.87495  0.12537  0.43223  11.00000  0.02516  0.03393  0.01528 =
 0.00828  0.00392  0.00951 
O2    3     1.14743  0.02168  0.75116  11.00000  0.03438  0.03936  0.01685 =
 0.00260 -0.00306  0.00145 
O3    3     0.71730 -0.05491  0.61569  11.00000  0.02586  0.02333  0.02014 =
 -0.00534  0.00861 -0.00535 
C1    1     0.93750  0.14221  0.57269  11.00000  0.02280  0.02165  0.01524 =
 0.00246  0.00254 -0.00140 
AFIX 13
H1    2     0.98807  0.26512  0.59160  11.00000 -1.20000 
AFIX 0
C2    1     1.07921  0.00887  0.63628  11.00000  0.01812  0.02728  0.01791 =
 0.00545  0.00244 -0.00330 
C3    1     0.77739  0.12457  0.63553  11.00000  0.02471  0.02007  0.01833 =
 -0.00284  0.00583 -0.00055 
AFIX 23
H3A   2     0.81215  0.15181  0.73055  11.00000 -1.20000 
H3B   2     0.68141  0.20834  0.59412  11.00000 -1.20000 
AFIX 0
C4    1     0.57617 -0.09289  0.68092  11.00000  0.02021  0.03668  0.02167 =
 -0.00128  0.00440 -0.00651 
AFIX 23
H4A   2     0.52690 -0.21296  0.65420  11.00000 -1.20000 
H4B   2     0.47885 -0.00456  0.65330  11.00000 -1.20000 
AFIX 0
C5    1     0.63627 -0.08750  0.82424  11.00000  0.02197  0.02578  0.02550 =
 0.00289  0.00963 -0.00119 
C6    1     0.68796 -0.08127  0.94064  11.00000  0.03396  0.03413  0.02106 =
 0.00157  0.00766  0.00068 
AFIX 163
H6    2     0.72910 -0.07630  1.03330  11.00000 -1.20000 
AFIX 0

Q1    1     1.14410 -0.12730  0.39950  11.00000  0.05000  0.180

Q2    1     0.97980 -0.08880  0.40080  11.00000  0.05000  0.160

Q3    1     0.86590  0.00970  0.43650  11.00000  0.05000  0.160

Q4    1     1.15710 -0.00440  0.42270  11.00000  0.05000  0.140
HKLF 4
END

;
_chemical_properties_physical    'Moisture-sensitive, Heat-sensitive'
_database_code_depnum_ccdc_archive 'CCDC 1029799'
