# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ix325
_database_code_depnum_ccdc_archive 'CCDC 1406377'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_audit_block_code                ?
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_audit_creation_date             
;
'Wed Jul 24 17:00:26 2013'
;

_chemical_name_systematic        'Tetraperoxidocyclohexane monohydrate'
_chemical_compound_source        ?
_chemical_name_common            'Tetraperoxidocyclohexane monohydrate'
_chemical_formula_moiety         ' C6 H12 O8, H2 O'
_chemical_formula_sum            'C6 H14 O9'
_chemical_formula_weight         230.17


_cell_length_a                   7.3942(9)
_cell_length_b                   9.2111(11)
_cell_length_c                   14.029(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.117(12)
_cell_angle_gamma                90.00
_cell_volume                     954.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    784
_cell_measurement_theta_min      4.6480
_cell_measurement_theta_max      32.9320
_cell_special_details            ?

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9405
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      100 # in K
_diffrn_source_type              'Spellman generator'
_diffrn_source_power             ? # in kW
_diffrn_source_voltage           50 # kV
_diffrn_source_current           40 # mA
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_collimation    0.5
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean 15.9809

_diffrn_reflns_number            2476
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         26.47
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.47
_diffrn_measured_fraction_theta_full 0.994

_reflns_number_total             985
_reflns_number_gt                780
_reflns_threshold_expression     >2sigma(I)

_diffrn_orient_matrix_UB_11      0.0569369000
_diffrn_orient_matrix_UB_12      -0.0445870000
_diffrn_orient_matrix_UB_13      0.0298915000
_diffrn_orient_matrix_UB_21      -0.0690927000
_diffrn_orient_matrix_UB_22      -0.0534203000
_diffrn_orient_matrix_UB_23      0.0002623000
_diffrn_orient_matrix_UB_31      0.0348848000
_diffrn_orient_matrix_UB_32      -0.0330099000
_diffrn_orient_matrix_UB_33      -0.0408437000

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc '

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'


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

_exptl_special_details           ?


loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

_diffrn_special_details          ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.052

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.7252P] where P=(Fo²+2Fc²)/3'


_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    SIR-92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;

_computing_publication_material  
;PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         985
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0762
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19581(15) -0.13464(12) 0.08959(8) 0.0159(3) Uani 1 1 d . . .
O3 O 0.23986(15) 0.10335(13) 0.14362(8) 0.0182(3) Uani 1 1 d . . .
O2 O 0.14945(17) -0.18330(14) 0.18500(8) 0.0193(3) Uani 1 1 d . . .
O4 O 0.43372(16) 0.08904(15) 0.12773(9) 0.0218(3) Uani 1 1 d . . .
C2 C 0.1415(2) 0.01222(18) 0.07657(11) 0.0144(4) Uani 1 1 d . . .
C3 C 0.1823(2) 0.0434(2) -0.02650(12) 0.0170(4) Uani 1 1 d . . .
C1 C -0.0560(2) 0.04121(19) 0.09656(13) 0.0170(4) Uani 1 1 d . . .
O5 O 0.0000 0.3671(2) 0.2500 0.0223(4) Uani 1 2 d S . .
H3B H 0.311(3) 0.015(2) -0.0377(12) 0.017(5) Uiso 1 1 d . . .
H1A H -0.075(2) 0.147(2) 0.0884(12) 0.016(5) Uiso 1 1 d . . .
H1B H -0.075(3) 0.013(2) 0.1635(14) 0.020(5) Uiso 1 1 d . . .
H5 H -0.090(3) 0.320(3) 0.2490(19) 0.054(8) Uiso 1 1 d . . .
H3A H 0.166(2) 0.147(2) -0.0370(12) 0.013(4) Uiso 1 1 d . . .
H4 H 0.459(3) 0.011(3) 0.1603(17) 0.049(8) Uiso 1 1 d . . .
H2 H 0.074(3) -0.256(3) 0.1672(18) 0.054(8) Uiso 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
O1 0.0182(6) 0.0139(6) 0.0154(6) 0.0027(5) 0.0001(5) 0.0009(5)
O3 0.0148(6) 0.0174(6) 0.0221(7) -0.0029(5) -0.0029(5) -0.0022(5)
O2 0.0216(7) 0.0192(7) 0.0167(6) 0.0050(5) -0.0025(5) -0.0044(5)
O4 0.0142(6) 0.0215(7) 0.0289(7) 0.0035(6) -0.0049(5) -0.0044(5)
C2 0.0155(8) 0.0122(8) 0.0151(8) -0.0013(6) -0.0023(7) -0.0018(6)
C3 0.0142(8) 0.0172(9) 0.0193(9) 0.0010(7) -0.0010(7) -0.0011(7)
C1 0.0180(9) 0.0162(9) 0.0164(9) -0.0001(7) -0.0021(7) 0.0011(7)
O5 0.0174(10) 0.0185(10) 0.0300(11) 0.000 -0.0067(8) 0.000

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 C2 1.4199(19) . ?
O1 O2 1.4697(16) . ?
O3 C2 1.4296(19) . ?
O3 O4 1.4685(16) . ?
O2 H2 0.90(3) . ?
O4 H4 0.87(3) . ?
C2 C3 1.521(2) . ?
C2 C1 1.526(2) . ?
C3 C1 1.532(2) 5 ?
C3 H3B 1.010(18) . ?
C3 H3A 0.973(18) . ?
C1 H1A 0.987(19) . ?
C1 H1B 0.993(19) . ?
O5 H5 0.79(2) . ?

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 O2 109.24(11) . . ?
C2 O3 O4 108.24(11) . . ?
O1 O2 H2 98.4(16) . . ?
O3 O4 H4 100.5(16) . . ?
O1 C2 O3 110.16(12) . . ?
O1 C2 C3 103.49(13) . . ?
O3 C2 C3 113.25(13) . . ?
O1 C2 C1 114.19(14) . . ?
O3 C2 C1 103.52(13) . . ?
C3 C2 C1 112.53(14) . . ?
C2 C3 C1 111.61(14) . 5 ?
C2 C3 H3B 109.7(10) . . ?
C1 C3 H3B 108.5(10) 5 . ?
C2 C3 H3A 107.4(10) . . ?
C1 C3 H3A 109.5(10) 5 . ?
H3B C3 H3A 110.1(14) . . ?
C2 C1 C3 110.46(14) . 5 ?
C2 C1 H1A 106.5(10) . . ?
C3 C1 H1A 110.3(10) 5 . ?
C2 C1 H1B 108.5(11) . . ?
C3 C1 H1B 111.0(11) 5 . ?
H1A C1 H1B 110.0(15) . . ?

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
O2 O1 C2 O3 63.29(15) . . . . ?
O2 O1 C2 C3 -175.35(11) . . . . ?
O2 O1 C2 C1 -52.69(16) . . . . ?
O4 O3 C2 O1 60.04(15) . . . . ?
O4 O3 C2 C3 -55.31(16) . . . . ?
O4 O3 C2 C1 -177.46(12) . . . . ?
O1 C2 C3 C1 68.60(17) . . . 5 ?
O3 C2 C3 C1 -172.14(14) . . . 5 ?
C1 C2 C3 C1 -55.2(2) . . . 5 ?
O1 C2 C1 C3 -63.05(18) . . . 5 ?
O3 C2 C1 C3 177.16(13) . . . 5 ?
C3 C2 C1 C3 54.5(2) . . . 5 ?

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O2 0.79(2) 2.08(2) 2.7403(13) 141(3) 3_455
O4 H4 O5 0.87(3) 1.84(3) 2.696(2) 169(2) 3_545
O2 H2 O4 0.90(3) 1.83(3) 2.7291(18) 176(2) 3_445

_geom_special_details            ?

_iucr_refine_instructions_details 
;

TITL v1 in C2/c
CELL  0.71073   7.3942   9.2111  14.0290   90.000   93.117   90.000
ZERR     4.00   0.0009   0.0011   0.0020    0.000    0.012    0.000
LATT   7
SYMM  - X,   Y, 1/2 - Z
SFAC  C    H    O
UNIT  24   56   36
MERG   2
OMIT    -2.00  53.00
OMIT    -4   4  11
EQIV $1 x-1/2, y+1/2, z
EQIV $2 x+1/2, y-1/2, z
EQIV $3 x-1/2, y-1/2, z
HTAB O5 O2_$1
HTAB O4 O5_$2
HTAB O2 O4_$3
FMAP   2
PLAN   20
SIZE     0.07   0.21   0.40
ACTA
BOND   $H
CONF
L.S.   5
TEMP  -173.00
WGHT    0.029900    0.725200
FVAR       0.19888
O1    3    0.195807   -0.134639    0.089590    11.00000    0.01821    0.01387 =
         0.01542    0.00270    0.00013    0.00087
O3    3    0.239859    0.103351    0.143624    11.00000    0.01480    0.01737 =
         0.02205   -0.00289   -0.00289   -0.00220
O2    3    0.149446   -0.183299    0.185003    11.00000    0.02160    0.01920 =
         0.01669    0.00498   -0.00250   -0.00436
O4    3    0.433716    0.089037    0.127735    11.00000    0.01418    0.02148 =
         0.02895    0.00354   -0.00493   -0.00444
C2    1    0.141544    0.012216    0.076566    11.00000    0.01553    0.01222 =
         0.01515   -0.00130   -0.00232   -0.00175
C3    1    0.182332    0.043436   -0.026505    11.00000    0.01420    0.01719 =
         0.01931    0.00099   -0.00095   -0.00112
C1    1   -0.055967    0.041206    0.096559    11.00000    0.01799    0.01624 =
         0.01644   -0.00013   -0.00206    0.00113
O5    3    0.000000    0.367128    0.250000    10.50000    0.01737    0.01854 =
         0.03001    0.00000   -0.00666    0.00000
H3B   2    0.311353    0.015094   -0.037732    11.00000    0.01693
H1A   2   -0.075196    0.146563    0.088424    11.00000    0.01590
H1B   2   -0.075361    0.012814    0.163491    11.00000    0.02004
H5    2   -0.090181    0.320317    0.248955    11.00000    0.05378
H3A   2    0.165578    0.147094   -0.036981    11.00000    0.01298
H4    2    0.459475    0.011128    0.160338    11.00000    0.04858
H2    2    0.074285   -0.255905    0.167210    11.00000    0.05432
HKLF    4
 
REM  v1 in C2/c
REM R1 =  0.0354 for    780 Fo > 4sig(Fo)  and  0.0502 for all    985 data
REM     97 parameters refined using      0 restraints
 
END
 
WGHT      0.0299      0.7252
REM Highest difference peak  0.337,  deepest hole -0.253,  1-sigma level  0.052
Q1    1  -0.1174  0.0052  0.0583  11.00000  0.05    0.34
Q2    1   0.1527  0.0125  0.0236  11.00000  0.05    0.31
Q3    1   0.0433  0.0253  0.0808  11.00000  0.05    0.25
Q4    1   0.1591 -0.0455  0.0856  11.00000  0.05    0.21
Q5    1   0.2109  0.0756  0.2096  11.00000  0.05    0.16
Q6    1   0.1840  0.0400  0.1073  11.00000  0.05    0.15
Q7    1   0.4794  0.1476  0.0856  11.00000  0.05    0.15
Q8    1  -0.0248 -0.1793  0.2217  11.00000  0.05    0.15
Q9    1  -0.1555  0.3747  0.3150  11.00000  0.05    0.15
Q10   1   0.4998  0.1314  0.1875  11.00000  0.05    0.15
Q11   1   0.0380 -0.1210  0.2052  11.00000  0.05    0.15
Q12   1   0.1867 -0.2405  0.0770  11.00000  0.05    0.14
Q13   1   0.0919 -0.2041  0.0471  11.00000  0.05    0.14
Q14   1   0.0748 -0.1680  0.1328  11.00000  0.05    0.13
Q15   1   0.0205  0.4071  0.1809  11.00000  0.05    0.13
Q16   1  -0.0544  0.3071  0.3159  11.00000  0.05    0.13
Q17   1   0.2161  0.0197  0.1346  11.00000  0.05    0.13
Q18   1   0.3370 -0.1403  0.0611  11.00000  0.05    0.13
Q19   1   0.2850  0.1740  0.2212  11.00000  0.05    0.12
Q20   1   0.0532  0.4748  0.2455  11.00000  0.05    0.12

;


####################################################################### 
# 
# 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_14dhpmb_p21ovrc_s
_database_code_depnum_ccdc_archive 'CCDC 1406378'
_audit_update_record             
;
2015-06-11 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1,4-bis(dihydroperoxymethyl)benzene
_chemical_name_common            ?
_chemical_melting_point          383
_chemical_formula_moiety         C8H10O8
_chemical_formula_sum            'C4 H5 O4'
_chemical_formula_weight         117.08

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.776(3)
_cell_length_b                   6.0458(16)
_cell_length_c                   8.133(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.964(11)
_cell_angle_gamma                90
_cell_volume                     471.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       columnar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26670
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.122
_diffrn_reflns_theta_max         39.088
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2643
_reflns_number_gt                2406
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0511P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2643
_refine_ls_number_parameters     79
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   2.008
_refine_ls_restrained_S_all      2.008
_refine_ls_shift/su_max          0.001
_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
O1 O 0.62083(5) 0.50700(8) 0.80265(5) 0.01286(12) Uani 1 1 d . . . . .
O2 O 0.62240(4) 0.38948(8) 0.96144(6) 0.01160(11) Uani 1 1 d . . . . .
O3 O 0.73468(4) 0.08333(7) 0.87196(6) 0.01062(11) Uani 1 1 d . . . . .
O4 O 0.62660(5) -0.06762(8) 0.90508(7) 0.01283(11) Uani 1 1 d . . . . .
C1 C 0.74255(5) 0.25486(10) 0.99114(7) 0.00892(12) Uani 1 1 d . . . . .
H3 H 0.7491 0.1852 1.1039 0.011 Uiso 1 1 calc R U . . .
C2 C 0.87602(6) 0.38078(9) 0.99153(7) 0.00831(11) Uani 1 1 d . . . . .
C3 C 0.89102(6) 0.59036(10) 1.06534(7) 0.00969(12) Uani 1 1 d . . . . .
H4 H 0.8167 0.6521 1.1103 0.012 Uiso 1 1 calc R U . . .
C4 C 0.98606(6) 0.29084(9) 0.92657(7) 0.00938(12) Uani 1 1 d . . . . .
H5 H 0.9770 0.1482 0.8767 0.011 Uiso 1 1 calc R U . . .
H2 H 0.5614(11) -0.0221(17) 0.8284(12) 0.014 Uiso 1 1 d . U . . .
H1 H 0.6359(10) 0.6376(17) 0.8406(13) 0.014 Uiso 1 1 d . U . . .

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 0.0126(2) 0.0094(2) 0.0150(2) 0.00061(15) -0.00143(16) 0.00086(14)
O2 0.00896(19) 0.0111(2) 0.0154(2) 0.00028(15) 0.00393(16) 0.00090(13)
O3 0.00903(19) 0.0083(2) 0.0147(2) -0.00227(14) 0.00265(16) -0.00308(13)
O4 0.00864(19) 0.0085(2) 0.0201(2) 0.00106(15) -0.00035(17) -0.00344(13)
C1 0.0080(2) 0.0081(2) 0.0104(2) -0.00069(17) 0.00105(17) -0.00041(16)
C2 0.0073(2) 0.0084(2) 0.0087(2) 0.00038(16) 0.00023(17) -0.00063(16)
C3 0.0082(2) 0.0097(2) 0.0112(3) -0.00144(17) 0.00191(19) -0.00039(16)
C4 0.0085(2) 0.0080(2) 0.0113(2) -0.00142(17) 0.00110(17) -0.00045(16)

_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 O2 1.4714(7) . ?
O1 H1 0.850(10) . ?
O2 C1 1.4115(8) . ?
O3 C1 1.4115(8) . ?
O3 O4 1.4594(7) . ?
O4 H2 0.849(11) . ?
C1 C2 1.5101(8) . ?
C1 H3 1.0000 . ?
C2 C4 1.3957(8) . ?
C2 C3 1.3978(9) . ?
C3 C4 1.3907(8) 3_767 ?
C3 H4 0.9500 . ?
C4 C3 1.3907(8) 3_767 ?
C4 H5 0.9500 . ?

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
O2 O1 H1 99.1(7) . . ?
C1 O2 O1 107.34(4) . . ?
C1 O3 O4 106.23(4) . . ?
O3 O4 H2 97.5(7) . . ?
O2 C1 O3 111.79(5) . . ?
O2 C1 C2 113.59(5) . . ?
O3 C1 C2 107.82(5) . . ?
O2 C1 H3 107.8 . . ?
O3 C1 H3 107.8 . . ?
C2 C1 H3 107.8 . . ?
C4 C2 C3 119.36(5) . . ?
C4 C2 C1 122.05(5) . . ?
C3 C2 C1 118.55(5) . . ?
C4 C3 C2 120.50(5) 3_767 . ?
C4 C3 H4 119.7 3_767 . ?
C2 C3 H4 119.7 . . ?
C3 C4 C2 120.14(6) 3_767 . ?
C3 C4 H5 119.9 3_767 . ?
C2 C4 H5 119.9 . . ?

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 O2 C1 O3 -66.84(6) . . . . ?
O1 O2 C1 C2 55.46(6) . . . . ?
O4 O3 C1 O2 -68.99(6) . . . . ?
O4 O3 C1 C2 165.47(4) . . . . ?
O2 C1 C2 C4 -143.40(6) . . . . ?
O3 C1 C2 C4 -18.94(7) . . . . ?
O2 C1 C2 C3 39.12(7) . . . . ?
O3 C1 C2 C3 163.58(5) . . . . ?
C4 C2 C3 C4 0.34(10) . . . 3_767 ?
C1 C2 C3 C4 177.89(5) . . . 3_767 ?
C3 C2 C4 C3 -0.34(10) . . . 3_767 ?
C1 C2 C4 C3 -177.80(5) . . . 3_767 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565
C1 H3 O1 1.00 2.51 3.3893(9) 146.3 4_566
C1 H3 O3 1.00 2.62 3.2627(10) 122.3 4_566
O4 H2 O1 0.849(11) 1.902(11) 2.7118(9) 159.2(9) 2_646
O1 H1 O4 0.850(10) 1.865(10) 2.7006(9) 167.2(10) 1_565

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL 14dhpmb_p21ovrc_s in P2(1)/c
CELL 0.71073 9.7757 6.0458 8.1326 90.000 100.964 90.000
ZERR 4.00 0.0026 0.0016 0.0020 0.000 0.011 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C  H  O
UNIT 16  20  16
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 12
ACTA
BOND $H
FMAP 2
PLAN -1
HTAB O1 O4_$3
HTAB O4 O1_$2
HTAB C1 O3_$1
HTAB C1 O1_$1
HTAB O1 O4_$3
HTAB O4 O1_$2
HTAB C1 O3_$1
HTAB C1 O1_$1
HTAB O1 O4_$3
HTAB O4 O1_$2
HTAB C1 O3_$1
HTAB C1 O1_$1
HTAB
CONF
EQIV $1 x, -y+1/2, z+1/2
HTAB C1 O1_$1
HTAB C1 O3_$1
EQIV $2 -x+1, y-1/2, -z+3/2
HTAB O4 O1_$2
EQIV $3 x, y+1, z
HTAB O1 O4_$3
HTAB C1 O1_$1
HTAB C1 O3_$1
HTAB O4 O1_$2
HTAB O1 O4_$3
HTAB C1 O1_$1
HTAB C1 O3_$1
HTAB O4 O1_$2
HTAB O1 O4_$3
TEMP -173.050
WGHT    0.051100
FVAR       0.38597
O1    3    0.620829    0.506997    0.802655    11.00000    0.01256    0.00945 =
         0.01498    0.00061   -0.00143    0.00086
O2    3    0.622398    0.389478    0.961443    11.00000    0.00896    0.01105 =
         0.01542    0.00028    0.00393    0.00090
O3    3    0.734678    0.083329    0.871959    11.00000    0.00903    0.00828 =
         0.01471   -0.00227    0.00265   -0.00308
O4    3    0.626604   -0.067617    0.905077    11.00000    0.00864    0.00854 =
         0.02008    0.00106   -0.00035   -0.00344
C1    1    0.742546    0.254864    0.991137    11.00000    0.00799    0.00809 =
         0.01040   -0.00069    0.00105   -0.00041
AFIX  13
H3    2    0.749093    0.185196    1.103888    11.00000   -1.20000
AFIX   0
C2    1    0.876024    0.380776    0.991532    11.00000    0.00734    0.00838 =
         0.00871    0.00038    0.00023   -0.00063
C3    1    0.891021    0.590362    1.065343    11.00000    0.00825    0.00969 =
         0.01115   -0.00144    0.00191   -0.00039
AFIX  43
H4    2    0.816679    0.652121    1.110322    11.00000   -1.20000
AFIX   0
C4    1    0.986058    0.290845    0.926567    11.00000    0.00852    0.00801 =
         0.01129   -0.00142    0.00110   -0.00045
AFIX  43
H5    2    0.976965    0.148180    0.876717    11.00000   -1.20000
AFIX   0
H2    2    0.561351   -0.022050    0.828395    11.00000   -1.50000
H1    2    0.635930    0.637616    0.840591    11.00000   -1.50000
HKLF 4 1 1 0 0 0 1 0 0 0 1

REM  14dhpmb_p21ovrc_s in P2(1)/c
REM R1 =  0.0328 for    2406 Fo > 4sig(Fo)  and  0.0363 for all    2643 data
REM     79 parameters refined using      0 restraints

END

WGHT      0.0511      0.1290

REM Instructions for potential hydrogen bonds
HTAB C1 O1_$1
HTAB C1 O3_$1
HTAB O4 O1_$2
HTAB O1 O4_$3

REM Highest difference peak  0.609,  deepest hole -0.377,  1-sigma level  0.067
Q1    1   0.9550  0.6478  1.0704  11.00000  0.05    0.61
;
_shelx_res_checksum              71718
