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

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#                                CCDC 
# 
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# 
#  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
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C8 F4 O4), H8 O4, 4(H2 O), 4(Ca)'
_chemical_formula_sum            'C32 H16 Ca4 F16 O24'
_chemical_formula_weight         1248.77

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   14.8357(7)
_cell_length_b                   14.8357(7)
_cell_length_c                   6.7854(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1493.45(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5309
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.43

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.478
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8777
_exptl_absorpt_correction_T_max  0.9021
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD '
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9683
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.746
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1720
_reflns_number_gt                1218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_max     1.001
_reflns_Friedel_fraction_full    1.000

_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       'SMART(Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT(Bruker, 2000)'
_computing_structure_solution    'SHELXTL(Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL(Bruker, 2000)'
_computing_publication_material  'SHELXTL(Bruker, 2000)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.055P)²+1.22P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1720
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3683(4) 0.6317(4) 0.2500 0.0438(18) Uani 1 2 d S T P . .
C2 C 0.2966(4) 0.7034(4) 0.2500 0.0454(19) Uani 1 2 d S T P . .
C3 C 0.3183(3) 0.7932(3) 0.2490(12) 0.0355(11) Uani 1 1 d . . . . .
C4 C 0.0898(4) 0.9102(4) 0.2500 0.0323(15) Uani 1 2 d S T P . .
C5 C 0.1612(3) 0.8388(3) 0.2500 0.0341(16) Uani 1 2 d S T P . .
C6 C 0.2528(3) 0.8583(4) 0.2541(11) 0.0395(12) Uani 1 1 d . . . . .
Ca1 Ca 0.54852(6) 0.54852(6) 0.0000 0.0221(3) Uani 1 2 d S T P . .
F1 F 0.4044(2) 0.8201(2) 0.2524(7) 0.0471(8) Uani 1 1 d . . . . .
F2 F 0.2783(2) 0.9460(2) 0.2534(6) 0.0440(7) Uani 1 1 d . . . . .
O1 O 0.4263(3) 0.6333(3) 0.1140(6) 0.0395(9) Uani 1 1 d . . . . .
O2 O 0.0434(3) 0.9197(2) 0.0991(5) 0.0382(9) Uani 1 1 d . . . . .
O2W O 0.7182(12) 0.8360(13) -0.007(4) 0.063(5) Uani 0.25 1 d . . P . .
H2X H 0.6860 0.8442 0.0949 0.076 Uiso 0.25 1 d R U P . .
H2Y H 0.7388 0.7844 0.0000 0.076 Uiso 0.25 1 d R U P . .
O3W O 0.5814(11) 0.0792(11) 0.246(3) 0.059(5) Uani 0.25 1 d . . P . .
H3X H 0.6292 0.0493 0.2234 0.071 Uiso 0.25 1 d R U P . .
H3Y H 0.5648 0.0709 0.3641 0.071 Uiso 0.25 1 d R U P . .
O1WA O 0.6149(12) 0.6924(12) -0.013(3) 0.042(4) Uani 0.25 1 d . . P A 1
H1X H 0.6720 0.6872 -0.0114 0.050 Uiso 0.25 1 d R U P A 1
H1Y H 0.5979 0.7215 0.0885 0.050 Uiso 0.25 1 d R U P A 1
O1WB O 0.6613(18) 0.646(2) -0.055(4) 0.051(7) Uani 0.25 1 d . . P A 2
H1A H 0.6829 0.6655 0.0527 0.062 Uiso 0.25 1 d R U P A 2
H1B H 0.7034 0.6233 -0.1243 0.062 Uiso 0.25 1 d R U P A 2

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 0.051(3) 0.051(3) 0.030(4) 0.002(3) 0.002(3) -0.011(4)
C2 0.044(3) 0.044(3) 0.048(5) -0.011(3) -0.011(3) -0.004(3)
C3 0.035(3) 0.030(2) 0.041(3) -0.005(3) -0.001(3) -0.005(2)
C4 0.029(2) 0.029(2) 0.039(4) 0.001(3) 0.001(3) -0.016(3)
C5 0.027(2) 0.027(2) 0.048(4) 0.007(3) 0.007(3) -0.010(3)
C6 0.031(3) 0.040(3) 0.047(3) -0.002(3) -0.008(3) -0.013(2)
Ca1 0.0203(4) 0.0203(4) 0.0256(6) -0.0021(4) 0.0021(4) 0.0006(5)
F1 0.0409(17) 0.0479(18) 0.0527(19) 0.003(2) 0.002(2) -0.0113(14)
F2 0.0378(16) 0.0442(17) 0.0500(17) -0.006(2) 0.0099(17) -0.0064(15)
O1 0.039(2) 0.033(2) 0.046(2) -0.0025(18) 0.0011(18) -0.0033(16)
O2 0.038(2) 0.040(2) 0.037(2) 0.0015(15) 0.0031(18) -0.0153(18)
O2W 0.054(10) 0.067(12) 0.069(12) -0.014(14) -0.015(12) 0.025(9)
O3W 0.051(10) 0.057(10) 0.069(12) 0.032(10) 0.028(10) 0.026(8)
O1WA 0.044(10) 0.033(10) 0.047(11) 0.006(10) 0.003(12) -0.003(7)
O1WB 0.021(10) 0.062(19) 0.071(18) -0.016(12) 0.021(10) -0.010(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.262(6) . ?
C1 O1 1.262(6) 8_665 ?
C1 C2 1.503(12) . ?
C2 C3 1.371(7) . ?
C2 C3 1.371(7) 8_665 ?
C3 F1 1.338(6) . ?
C3 C6 1.371(8) . ?
C4 O2 1.242(5) . ?
C4 O2 1.242(5) 8_665 ?
C4 C5 1.498(11) . ?
C4 Ca1 2.903(8) 3 ?
C5 C6 1.390(6) 8_665 ?
C5 C6 1.390(6) . ?
C6 F2 1.354(6) . ?
Ca1 O1WB 2.245(18) 7 ?
Ca1 O1WB 2.245(18) . ?
Ca1 O1 2.338(4) 7 ?
Ca1 O1 2.338(4) . ?
Ca1 O1WA 2.353(18) 7 ?
Ca1 O1WA 2.353(18) . ?
Ca1 O2 2.416(4) 3_655 ?
Ca1 O2 2.416(4) 6_564 ?
Ca1 O2 2.561(4) 4_454 ?
Ca1 O2 2.561(4) 5_545 ?
Ca1 C4 2.903(8) 4_454 ?
Ca1 H1X 2.7551 . ?
Ca1 H1Y 2.7361 . ?
Ca1 H1A 2.6678 . ?
Ca1 H1B 2.6873 . ?
O2 Ca1 2.416(4) 4_464 ?
O2 Ca1 2.561(4) 3 ?
O2W H2X 0.8499 . ?
O2W H2Y 0.8250 . ?
O3W H3X 0.8500 . ?
O3W H3Y 0.8500 . ?
O1WA O1WA 1.64(4) 7 ?
O1WA H1X 0.8500 . ?
O1WA H1Y 0.8500 . ?
O1WB O1WB 0.82(4) 7 ?
O1WB H1A 0.8501 . ?
O1WB H1B 0.8500 . ?

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
O1 C1 O1 124.0(8) . 8_665 ?
O1 C1 C2 118.0(4) . . ?
O1 C1 C2 118.0(4) 8_665 . ?
C3 C2 C3 117.1(7) . 8_665 ?
C3 C2 C1 121.4(4) . . ?
C3 C2 C1 121.4(4) 8_665 . ?
F1 C3 C6 117.7(4) . . ?
F1 C3 C2 120.9(5) . . ?
C6 C3 C2 121.3(5) . . ?
O2 C4 O2 123.6(7) . 8_665 ?
O2 C4 C5 118.2(4) . . ?
O2 C4 C5 118.2(4) 8_665 . ?
O2 C4 Ca1 61.8(4) . 3 ?
O2 C4 Ca1 61.8(4) 8_665 3 ?
C5 C4 Ca1 180.0(4) . 3 ?
C6 C5 C6 114.1(7) 8_665 . ?
C6 C5 C4 122.9(3) 8_665 . ?
C6 C5 C4 122.9(3) . . ?
F2 C6 C3 118.7(4) . . ?
F2 C6 C5 118.2(5) . . ?
C3 C6 C5 123.0(5) . . ?
O1WB Ca1 O1WB 20.9(10) 7 . ?
O1WB Ca1 O1 106.7(8) 7 7 ?
O1WB Ca1 O1 92.5(8) . 7 ?
O1WB Ca1 O1 92.5(8) 7 . ?
O1WB Ca1 O1 106.7(8) . . ?
O1 Ca1 O1 160.6(2) 7 . ?
O1 Ca1 O1WA 81.3(5) 7 7 ?
O1 Ca1 O1WA 117.8(5) . 7 ?
O1 Ca1 O1WA 117.8(5) 7 . ?
O1 Ca1 O1WA 81.3(5) . . ?
O1WB Ca1 O2 74.6(8) 7 3_655 ?
O1WB Ca1 O2 92.2(8) . 3_655 ?
O1 Ca1 O2 101.24(13) 7 3_655 ?
O1 Ca1 O2 81.02(13) . 3_655 ?
O1WA Ca1 O2 78.5(6) 7 3_655 ?
O1WA Ca1 O2 89.0(6) . 3_655 ?
O1WB Ca1 O2 92.2(8) 7 6_564 ?
O1WB Ca1 O2 74.6(8) . 6_564 ?
O1 Ca1 O2 81.02(13) 7 6_564 ?
O1 Ca1 O2 101.24(13) . 6_564 ?
O1WA Ca1 O2 89.0(6) 7 6_564 ?
O1WA Ca1 O2 78.5(6) . 6_564 ?
O2 Ca1 O2 166.7(2) 3_655 6_564 ?
O1WB Ca1 O2 160.9(11) 7 4_454 ?
O1WB Ca1 O2 146.4(8) . 4_454 ?
O1 Ca1 O2 81.72(13) 7 4_454 ?
O1 Ca1 O2 80.79(12) . 4_454 ?
O1WA Ca1 O2 156.2(6) 7 4_454 ?
O1WA Ca1 O2 141.3(5) . 4_454 ?
O2 Ca1 O2 121.38(11) 3_655 4_454 ?
O2 Ca1 O2 71.84(15) 6_564 4_454 ?
O1WB Ca1 O2 146.4(8) 7 5_545 ?
O1WB Ca1 O2 160.9(11) . 5_545 ?
O1 Ca1 O2 80.79(12) 7 5_545 ?
O1 Ca1 O2 81.73(13) . 5_545 ?
O1WA Ca1 O2 141.3(5) 7 5_545 ?
O1WA Ca1 O2 156.2(6) . 5_545 ?
O2 Ca1 O2 71.84(15) 3_655 5_545 ?
O2 Ca1 O2 121.38(11) 6_564 5_545 ?
O2 Ca1 O2 50.61(17) 4_454 5_545 ?
O1WB Ca1 C4 169.5(5) 7 4_454 ?
O1WB Ca1 C4 169.5(5) . 4_454 ?
O1 Ca1 C4 80.32(10) 7 4_454 ?
O1 Ca1 C4 80.32(10) . 4_454 ?
O1WA Ca1 C4 159.7(4) 7 4_454 ?
O1WA Ca1 C4 159.7(4) . 4_454 ?
O2 Ca1 C4 96.64(10) 3_655 4_454 ?
O2 Ca1 C4 96.64(10) 6_564 4_454 ?
O2 Ca1 C4 25.31(9) 4_454 4_454 ?
O2 Ca1 C4 25.31(9) 5_545 4_454 ?
O1WB Ca1 Ca1 130.5(8) 7 2_664 ?
O1WB Ca1 Ca1 111.3(7) . 2_664 ?
O1 Ca1 Ca1 68.27(10) 7 2_664 ?
O1 Ca1 Ca1 101.37(10) . 2_664 ?
O1WA Ca1 Ca1 120.9(6) 7 2_664 ?
O1WA Ca1 Ca1 116.8(6) . 2_664 ?
O2 Ca1 Ca1 154.17(11) 3_655 2_664 ?
O2 Ca1 Ca1 36.10(8) 4_454 2_664 ?
O2 Ca1 Ca1 82.97(10) 5_545 2_664 ?
C4 Ca1 Ca1 59.03(3) 4_454 2_664 ?
O1 Ca1 H1X 102.2 7 . ?
O1 Ca1 H1X 97.1 . . ?
O1WA Ca1 H1X 23.8 7 . ?
O1WA Ca1 H1X 16.9 . . ?
O2 Ca1 H1X 85.5 3_655 . ?
O2 Ca1 H1X 81.2 6_564 . ?
O2 Ca1 H1X 151.9 4_454 . ?
O2 Ca1 H1X 157.2 5_545 . ?
C4 Ca1 H1X 176.3 4_454 . ?
Ca1 Ca1 H1X 119.3 2_664 . ?
O1 Ca1 H1Y 131.0 7 . ?
O1 Ca1 H1Y 68.3 . . ?
O1WA Ca1 H1Y 49.9 7 . ?
O1WA Ca1 H1Y 17.2 . . ?
O2 Ca1 H1Y 76.2 3_655 . ?
O2 Ca1 H1Y 92.3 6_564 . ?
O2 Ca1 H1Y 141.9 4_454 . ?
O2 Ca1 H1Y 139.0 5_545 . ?
C4 Ca1 H1Y 148.5 4_454 . ?
Ca1 Ca1 H1Y 128.8 2_664 . ?
H1X Ca1 H1Y 29.3 . . ?
O1WB Ca1 H1A 8.2 7 . ?
O1WB Ca1 H1A 17.3 . . ?
O1 Ca1 H1A 98.5 7 . ?
O1 Ca1 H1A 100.7 . . ?
O2 Ca1 H1A 75.1 3_655 . ?
O2 Ca1 H1A 91.6 6_564 . ?
O2 Ca1 H1A 163.3 4_454 . ?
O2 Ca1 H1A 146.1 5_545 . ?
C4 Ca1 H1A 171.4 4_454 . ?
Ca1 Ca1 H1A 128.6 2_664 . ?
O1WB Ca1 H1B 36.2 7 . ?
O1WB Ca1 H1B 17.0 . . ?
O1 Ca1 H1B 75.9 7 . ?
O1 Ca1 H1B 123.0 . . ?
O2 Ca1 H1B 98.9 3_655 . ?
O2 Ca1 H1B 68.8 6_564 . ?
O2 Ca1 H1B 137.1 4_454 . ?
O2 Ca1 H1B 152.7 5_545 . ?
C4 Ca1 H1B 153.7 4_454 . ?
Ca1 Ca1 H1B 101.1 2_664 . ?
H1A Ca1 H1B 30.0 . . ?
C1 O1 Ca1 139.6(4) . . ?
C4 O2 Ca1 144.4(3) . 4_464 ?
C4 O2 Ca1 92.9(4) . 3 ?
Ca1 O2 Ca1 105.26(14) 4_464 3 ?
H2X O2W H2Y 107.0 . . ?
H3X O3W H3Y 109.5 . . ?
O1WA O1WA Ca1 69.7(4) 7 . ?
Ca1 O1WA H1X 109.5 . . ?
O1WA O1WA H1Y 118.7 7 . ?
Ca1 O1WA H1Y 107.9 . . ?
H1X O1WA H1Y 109.5 . . ?
O1WB O1WB Ca1 79.5(5) 7 . ?
Ca1 O1WB H1A 110.8 . . ?
O1WB O1WB H1B 145.1 7 . ?
Ca1 O1WB H1B 112.5 . . ?
H1A O1WB H1B 109.5 . . ?

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 C3 -55.6(4) . . . . ?
O1 C1 C2 C3 124.4(4) 8_665 . . . ?
O1 C1 C2 C3 124.4(4) . . . 8_665 ?
O1 C1 C2 C3 -55.6(4) 8_665 . . 8_665 ?
C3 C2 C3 F1 178.6(8) 8_665 . . . ?
C1 C2 C3 F1 -1.4(8) . . . . ?
C3 C2 C3 C6 1.7(5) 8_665 . . . ?
C1 C2 C3 C6 -178.3(5) . . . . ?
O2 C4 C5 C6 -67.9(4) . . . 8_665 ?
O2 C4 C5 C6 112.1(4) 8_665 . . 8_665 ?
O2 C4 C5 C6 112.1(4) . . . . ?
O2 C4 C5 C6 -67.9(4) 8_665 . . . ?
F1 C3 C6 F2 2.9(10) . . . . ?
C2 C3 C6 F2 179.8(6) . . . . ?
F1 C3 C6 C5 179.5(6) . . . . ?
C2 C3 C6 C5 -3.5(10) . . . . ?
C6 C5 C6 F2 178.4(7) 8_665 . . . ?
C4 C5 C6 F2 -1.6(7) . . . . ?
C6 C5 C6 C3 1.7(5) 8_665 . . . ?
C4 C5 C6 C3 -178.3(5) . . . . ?
O1 C1 O1 Ca1 4.1(3) 8_665 . . . ?
C2 C1 O1 Ca1 -175.9(3) . . . . ?
O2 C4 O2 Ca1 121.5(6) 8_665 . . 4_464 ?
C5 C4 O2 Ca1 -58.5(6) . . . 4_464 ?
Ca1 C4 O2 Ca1 121.5(6) 3 . . 4_464 ?
O2 C4 O2 Ca1 -0.001(2) 8_665 . . 3 ?
C5 C4 O2 Ca1 180.000(1) . . . 3 ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.083

_shelxl_version_number           2013-2

_shelx_res_file                  
;
TITL mo_120426p_0m in P4(1)2(1)2
CELL 0.71073  14.8357  14.8357   6.7854  90.000  90.000  90.000
ZERR       1   0.0007   0.0007   0.0006   0.000   0.000   0.000
LATT -1
SYMM -X, -Y, 0.5+Z
SYMM 0.5-Y, 0.5+X, 0.25+Z
SYMM 0.5+Y, 0.5-X, 0.75+Z
SYMM 0.5-X, 0.5+Y, 0.25-Z
SYMM 0.5+X, 0.5-Y, 0.75-Z
SYMM Y, X, -Z
SYMM -Y, -X, 0.5-Z
SFAC C  H  O  F  Ca
UNIT 32 16 24 16 4
omit  -3   4   1
omit   3  12   1
omit   0   9   2
omit   0   2   4
L.S. 10
ACTA
BOND $h
FMAP 2
PLAN 2
conf
size 0.28 0.24 0.22
twin
TEMP 18
WGHT    0.055000    1.220000
BASF   0.04869
FVAR       0.59938
C1    1    0.368274    0.631726    0.250000    10.50000    0.05068    0.05068 =
         0.02995    0.00225    0.00225   -0.01108
C2    1    0.296628    0.703372    0.250000    10.50000    0.04423    0.04423 =
         0.04777   -0.01144   -0.01144   -0.00374
C3    1    0.318314    0.793193    0.249049    11.00000    0.03531    0.03005 =
         0.04111   -0.00534   -0.00147   -0.00517
C4    1    0.089832    0.910168    0.250000    10.50000    0.02896    0.02896 =
         0.03893    0.00123    0.00123   -0.01646
C5    1    0.161216    0.838784    0.250000    10.50000    0.02701    0.02701 =
         0.04832    0.00710    0.00710   -0.01012
C6    1    0.252831    0.858341    0.254112    11.00000    0.03134    0.03999 =
         0.04721   -0.00166   -0.00763   -0.01326
CA1   5    0.548520    0.548520    0.000000    10.50000    0.02030    0.02030 =
         0.02558   -0.00211    0.00211    0.00057
F1    4    0.404374    0.820097    0.252355    11.00000    0.04086    0.04788 =
         0.05270    0.00264    0.00185   -0.01133
F2    4    0.278273    0.946006    0.253380    11.00000    0.03778    0.04422 =
         0.05002   -0.00581    0.00993   -0.00641
O1    3    0.426307    0.633259    0.114013    11.00000    0.03914    0.03307 =
         0.04618   -0.00248    0.00105   -0.00327
O2    3    0.043387    0.919701    0.099069    11.00000    0.03795    0.03992 =
         0.03668    0.00152    0.00313   -0.01525
O2W   3    0.718209    0.836009   -0.007125    10.25000    0.05358    0.06676 =
         0.06856   -0.01378   -0.01510    0.02451
AFIX   3
H2X   2    0.686029    0.844209    0.094945    10.25000   -1.20000
H2Y   2    0.738779    0.784449   -0.000025    10.25000   -1.20000
AFIX   0
O3W   3    0.581373    0.079189    0.245533    10.25000    0.05121    0.05672 =
         0.06882    0.03193    0.02836    0.02616
AFIX   3
H3X   2    0.629213    0.049329    0.223383    10.25000   -1.20000
H3Y   2    0.564823    0.070929    0.364093    10.25000   -1.20000
PART 1
AFIX   0
O1WA  3    0.614923    0.692420   -0.012792    10.25000    0.04417    0.03334 =
         0.04739    0.00561    0.00335   -0.00323
AFIX   3
H1X   2    0.671973    0.687150   -0.011412    10.25000   -1.20000
H1Y   2    0.597923    0.721540    0.088478    10.25000   -1.20000
PART 2
AFIX   0
O1WB  3    0.661336    0.646103   -0.055321    10.25000    0.02082    0.06244 =
         0.07056   -0.01576    0.02102   -0.01022
AFIX   3
H1A   2    0.682916    0.665543    0.052669    10.25000   -1.20000
H1B   2    0.703386    0.623323   -0.124311    10.25000   -1.20000
PART 0
AFIX   0
HKLF 4

REM  mo_120426p_0m in P4(1)2(1)2
REM R1 =  0.0525 for    1218 Fo > 4sig(Fo)  and  0.0560 for all    1720 data
REM    117 parameters refined using      0 restraints

END

WGHT      0.0651      0.0000

REM Highest difference peak  0.333,  deepest hole -0.285,  1-sigma level  0.083
Q1    1   0.2193  0.7807  0.2500  10.50000  0.05    0.33
Q2    1   0.7223  0.7223  0.0000  10.50000  0.05    0.31
;
_shelx_res_checksum              61072
_database_code_depnum_ccdc_archive 'CCDC 1003028'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 Ca F4 O6'
_chemical_formula_weight         340.24

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'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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'

_cell_length_a                   10.95(2)
_cell_length_b                   17.70(3)
_cell_length_c                   7.843(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.33(4)
_cell_angle_gamma                90.00
_cell_volume                     1485(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1558
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      26.26

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8837
_exptl_absorpt_correction_T_max  0.8919
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3514
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1248
_reflns_number_gt                945
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1674P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1248
_refine_ls_number_parameters     97
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0639
_refine_ls_wR_factor_ref         0.2168
_refine_ls_wR_factor_gt          0.1978
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Ca1 Ca 0.5000 0.53217(6) 0.2500 0.0240(5) Uani 1 2 d S . .
C1 C 0.3590(3) 0.4000(2) 0.0925(5) 0.0264(9) Uani 1 1 d . . .
C2 C 0.3026(3) 0.3232(2) 0.0441(5) 0.0281(9) Uani 1 1 d . . .
C3 C 0.1788(4) 0.3077(3) 0.0379(8) 0.0490(13) Uani 1 1 d . . .
C4 C 0.1274(4) 0.2376(3) -0.0060(7) 0.0492(14) Uani 1 1 d . . .
C5 C 0.2057(6) 0.6039(6) 0.0819(11) 0.124(4) Uani 1 1 d . . .
H5A H 0.1591 0.5723 -0.0086 0.186 Uiso 1 1 calc R . .
H5B H 0.1765 0.6550 0.0642 0.186 Uiso 1 1 calc R . .
H5C H 0.1945 0.5864 0.1933 0.186 Uiso 1 1 calc R . .
F1 F 0.1048(3) 0.36471(19) 0.0712(8) 0.118(2) Uani 1 1 d . . .
F2 F 0.0047(3) 0.22824(19) -0.0119(8) 0.1108(19) Uani 1 1 d . . .
O1 O 0.3537(3) 0.42601(16) 0.2372(4) 0.0379(8) Uani 1 1 d . . .
O2 O 0.4116(3) 0.43239(15) -0.0156(4) 0.0347(8) Uani 1 1 d . . .
O3 O 0.3317(3) 0.6010(2) 0.0773(4) 0.0461(9) Uani 1 1 d . . .
H3 H 0.3442 0.6025 -0.0221 0.069 Uiso 1 1 d 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
Ca1 0.0245(7) 0.0203(7) 0.0274(7) 0.000 0.0056(4) 0.000
C1 0.0233(18) 0.025(2) 0.029(2) -0.0006(16) 0.0022(15) -0.0030(14)
C2 0.030(2) 0.025(2) 0.028(2) -0.0018(16) 0.0041(15) -0.0065(15)
C3 0.033(2) 0.032(3) 0.086(4) -0.021(2) 0.023(2) -0.0050(19)
C4 0.020(2) 0.041(3) 0.090(4) -0.021(2) 0.018(2) -0.0091(18)
C5 0.049(4) 0.253(12) 0.067(5) -0.001(6) 0.005(3) 0.044(6)
F1 0.045(2) 0.051(2) 0.268(6) -0.066(3) 0.056(3) -0.0105(15)
F2 0.0330(17) 0.053(2) 0.254(6) -0.052(3) 0.048(2) -0.0188(15)
O1 0.0437(17) 0.0365(17) 0.0344(18) -0.0078(13) 0.0106(13) -0.0103(13)
O2 0.0381(16) 0.0337(17) 0.0331(17) 0.0041(12) 0.0092(12) -0.0083(12)
O3 0.0402(18) 0.060(2) 0.0387(19) 0.0092(15) 0.0091(13) 0.0218(15)

_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
Ca1 O3 2.377(4) . ?
Ca1 O1 2.457(4) . ?
Ca1 O2 2.745(4) . ?
C1 O1 1.238(5) . ?
C1 O2 1.260(5) . ?
C1 C2 1.506(5) . ?
C2 C3 1.374(6) . ?
C2 C4 1.390(6) 7 ?
C3 F1 1.355(6) . ?
C3 C4 1.376(6) . ?
C4 F2 1.345(5) . ?
C4 C2 1.390(6) 7 ?
C5 O3 1.388(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
O3 H3 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Ca1 O1 87.09(17) . . ?
O3 Ca1 O2 78.02(15) . . ?
O1 Ca1 O2 49.89(11) . . ?
O1 C1 O2 124.4(4) . . ?
O1 C1 C2 118.0(3) . . ?
O2 C1 C2 117.6(3) . . ?
C3 C2 C4 115.0(4) . 7 ?
C3 C2 C1 122.5(4) . . ?
C4 C2 C1 122.5(4) 7 . ?
F1 C3 C2 118.1(4) . . ?
F1 C3 C4 119.4(4) . . ?
C2 C3 C4 122.5(4) . . ?
F2 C4 C3 118.2(4) . . ?
F2 C4 C2 119.4(4) . 7 ?
C3 C4 C2 122.5(4) . 7 ?
O3 C5 H5A 109.5 . . ?
O3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 O1 Ca1 99.5(2) . . ?
C1 O2 Ca1 85.5(3) . . ?
C5 O3 Ca1 131.1(4) . . ?
C5 O3 H3 113.1 . . ?
Ca1 O3 H3 107.0 . . ?

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 C3 58.9(6) . . . . ?
O2 C1 C2 C3 -123.0(5) . . . . ?
O1 C1 C2 C4 -119.7(5) . . . 7 ?
O2 C1 C2 C4 58.3(6) . . . 7 ?
C4 C2 C3 F1 -179.0(5) 7 . . . ?
C1 C2 C3 F1 2.2(8) . . . . ?
C4 C2 C3 C4 -1.2(9) 7 . . . ?
C1 C2 C3 C4 -179.9(5) . . . . ?
F1 C3 C4 F2 -0.9(9) . . . . ?
C2 C3 C4 F2 -178.7(6) . . . . ?
F1 C3 C4 C2 179.1(5) . . . 7 ?
C2 C3 C4 C2 1.2(9) . . . 7 ?
O2 C1 O1 Ca1 -10.1(4) . . . . ?
C2 C1 O1 Ca1 167.7(3) . . . . ?
O3 Ca1 O1 C1 81.8(3) . . . . ?
O2 Ca1 O1 C1 5.0(2) . . . . ?
O1 C1 O2 Ca1 9.0(4) . . . . ?
C2 C1 O2 Ca1 -168.9(3) . . . . ?
O3 Ca1 O2 C1 -101.2(3) . . . . ?
O1 Ca1 O2 C1 -4.9(2) . . . . ?
O1 Ca1 O3 C5 39.6(6) . . . . ?
O2 Ca1 O3 C5 89.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.946
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.126
_database_code_depnum_ccdc_archive 'CCDC 1003029'
#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 Ca F4 O8'
_chemical_formula_weight         348.22

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   3.7395(12)
_cell_length_b                   22.568(7)
_cell_length_c                   6.767(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.286(6)
_cell_angle_gamma                90.00
_cell_volume                     570.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3082
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      30.18

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.028
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8389
_exptl_absorpt_correction_T_max  0.8702
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3060
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1012
_reflns_number_gt                994
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.3859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.298(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1012
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
Ca1 Ca 0.08478(12) 0.7500 0.40808(7) 0.0202(2) Uani 1 2 d S . .
C1 C -0.0665(4) 0.62832(8) 0.0687(2) 0.0187(4) Uani 1 1 d . . .
C2 C -0.0313(5) 0.56196(7) 0.0331(3) 0.0185(4) Uani 1 1 d . . .
C3 C 0.0833(5) 0.53946(8) -0.1447(3) 0.0207(4) Uani 1 1 d . . .
C4 C 0.1156(5) 0.47925(8) -0.1763(3) 0.0199(4) Uani 1 1 d . . .
F1 F 0.1749(3) 0.57688(5) -0.28900(16) 0.0320(3) Uani 1 1 d . . .
F2 F 0.2431(3) 0.46076(5) -0.34834(16) 0.0320(3) Uani 1 1 d . . .
O1 O 0.0743(4) 0.64861(5) 0.22570(19) 0.0252(3) Uani 1 1 d . . .
O2 O -0.2430(4) 0.65743(5) -0.06334(19) 0.0269(4) Uani 1 1 d . . .
O3 O 0.1357(5) 0.7500 0.7678(3) 0.0268(5) Uani 1 2 d S . .
H3 H 0.0648 0.7195 0.8280 0.040 Uiso 1 1 d R . .
O4 O -0.4091(3) 0.68026(6) 0.52735(18) 0.0238(3) Uani 1 1 d . . .
H4A H -0.4170 0.6424 0.4597 0.029 Uiso 1 1 calc R . .
H4B H -0.3952 0.6745 0.6696 0.029 Uiso 1 1 calc R . .
O5 O 0.5570(4) 0.7500 0.1719(2) 0.0178(4) Uani 1 2 d S . .
H5 H 0.5710 0.7215 0.0908 0.027 Uiso 1 1 d 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
Ca1 0.0149(3) 0.0298(4) 0.0159(3) 0.000 -0.00012(19) 0.000
C1 0.0216(9) 0.0155(9) 0.0192(9) -0.0012(6) 0.0034(7) -0.0011(6)
C2 0.0207(8) 0.0164(8) 0.0181(9) -0.0018(7) -0.0023(6) -0.0004(7)
C3 0.0248(9) 0.0196(9) 0.0174(9) 0.0027(7) -0.0008(7) -0.0027(7)
C4 0.0241(9) 0.0203(9) 0.0154(8) -0.0031(7) 0.0013(6) 0.0006(7)
F1 0.0529(8) 0.0209(6) 0.0231(6) 0.0040(4) 0.0092(5) -0.0054(5)
F2 0.0502(7) 0.0256(6) 0.0215(6) -0.0048(5) 0.0124(5) 0.0012(5)
O1 0.0308(7) 0.0204(7) 0.0238(7) -0.0049(5) -0.0049(5) -0.0002(5)
O2 0.0400(8) 0.0189(7) 0.0210(7) -0.0007(5) -0.0046(5) 0.0057(6)
O3 0.0304(10) 0.0303(10) 0.0196(10) 0.000 0.0019(7) 0.000
O4 0.0310(7) 0.0233(7) 0.0168(6) -0.0010(5) -0.0004(5) 0.0001(5)
O5 0.0240(9) 0.0145(8) 0.0147(8) 0.000 0.0008(7) 0.000

_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
Ca1 O3 2.431(2) . ?
Ca1 O5 2.4487(18) . ?
Ca1 O5 2.4672(18) 1_455 ?
Ca1 O4 2.5564(14) 4_675 ?
Ca1 O4 2.5565(14) 1_655 ?
Ca1 O4 2.5903(14) 4_575 ?
Ca1 O4 2.5904(14) . ?
Ca1 O1 2.5990(14) . ?
Ca1 O1 2.5990(14) 4_575 ?
Ca1 Ca1 3.7395(12) 1_455 ?
Ca1 Ca1 3.7395(12) 1_655 ?
C1 O1 1.245(2) . ?
C1 O2 1.264(2) . ?
C1 C2 1.524(2) . ?
C2 C4 1.392(3) 3_565 ?
C2 C3 1.396(3) . ?
C3 F1 1.350(2) . ?
C3 C4 1.382(3) . ?
C4 F2 1.349(2) . ?
C4 C2 1.392(3) 3_565 ?
O3 H3 0.8500 . ?
O4 Ca1 2.5565(14) 1_455 ?
O4 H4A 0.9700 . ?
O4 H4B 0.9700 . ?
O5 Ca1 2.4672(18) 1_655 ?
O5 H5 0.8500 . ?

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
O3 Ca1 O5 129.46(6) . . ?
O3 Ca1 O5 131.49(6) . 1_455 ?
O5 Ca1 O5 99.05(7) . 1_455 ?
O3 Ca1 O4 70.72(5) . 4_675 ?
O5 Ca1 O4 69.97(5) . 4_675 ?
O5 Ca1 O4 139.00(3) 1_455 4_675 ?
O3 Ca1 O4 70.72(5) . 1_655 ?
O5 Ca1 O4 69.97(5) . 1_655 ?
O5 Ca1 O4 139.00(3) 1_455 1_655 ?
O4 Ca1 O4 76.00(6) 4_675 1_655 ?
O3 Ca1 O4 72.80(5) . 4_575 ?
O5 Ca1 O4 139.21(3) . 4_575 ?
O5 Ca1 O4 69.13(5) 1_455 4_575 ?
O4 Ca1 O4 93.20(5) 4_675 4_575 ?
O4 Ca1 O4 143.50(6) 1_655 4_575 ?
O3 Ca1 O4 72.80(5) . . ?
O5 Ca1 O4 139.21(3) . . ?
O5 Ca1 O4 69.13(5) 1_455 . ?
O4 Ca1 O4 143.50(6) 4_675 . ?
O4 Ca1 O4 93.20(5) 1_655 . ?
O4 Ca1 O4 74.83(6) 4_575 . ?
O3 Ca1 O1 118.27(3) . . ?
O5 Ca1 O1 71.45(4) . . ?
O5 Ca1 O1 72.70(3) 1_455 . ?
O4 Ca1 O1 133.05(5) 4_675 . ?
O4 Ca1 O1 66.34(4) 1_655 . ?
O4 Ca1 O1 133.73(5) 4_575 . ?
O4 Ca1 O1 67.75(4) . . ?
O3 Ca1 O1 118.27(3) . 4_575 ?
O5 Ca1 O1 71.45(4) . 4_575 ?
O5 Ca1 O1 72.70(3) 1_455 4_575 ?
O4 Ca1 O1 66.34(4) 4_675 4_575 ?
O4 Ca1 O1 133.05(5) 1_655 4_575 ?
O4 Ca1 O1 67.75(4) 4_575 4_575 ?
O4 Ca1 O1 133.73(5) . 4_575 ?
O1 Ca1 O1 123.38(6) . 4_575 ?
O3 Ca1 Ca1 91.20(5) . 1_455 ?
O5 Ca1 Ca1 139.34(4) . 1_455 ?
O5 Ca1 Ca1 40.29(4) 1_455 1_455 ?
O4 Ca1 Ca1 136.24(3) 4_675 1_455 ?
O4 Ca1 Ca1 136.24(3) 1_655 1_455 ?
O4 Ca1 Ca1 43.04(3) 4_575 1_455 ?
O4 Ca1 Ca1 43.05(3) . 1_455 ?
O1 Ca1 Ca1 90.69(3) . 1_455 ?
O1 Ca1 Ca1 90.69(3) 4_575 1_455 ?
O3 Ca1 Ca1 88.80(5) . 1_655 ?
O5 Ca1 Ca1 40.66(4) . 1_655 ?
O5 Ca1 Ca1 139.71(4) 1_455 1_655 ?
O4 Ca1 Ca1 43.76(3) 4_675 1_655 ?
O4 Ca1 Ca1 43.76(3) 1_655 1_655 ?
O4 Ca1 Ca1 136.96(3) 4_575 1_655 ?
O4 Ca1 Ca1 136.95(3) . 1_655 ?
O1 Ca1 Ca1 89.31(3) . 1_655 ?
O1 Ca1 Ca1 89.31(3) 4_575 1_655 ?
Ca1 Ca1 Ca1 180.0 1_455 1_655 ?
O1 C1 O2 126.14(16) . . ?
O1 C1 C2 117.39(15) . . ?
O2 C1 C2 116.45(15) . . ?
C4 C2 C3 116.74(16) 3_565 . ?
C4 C2 C1 121.43(16) 3_565 . ?
C3 C2 C1 121.83(16) . . ?
F1 C3 C4 118.35(16) . . ?
F1 C3 C2 119.94(16) . . ?
C4 C3 C2 121.68(17) . . ?
F2 C4 C3 118.43(16) . . ?
F2 C4 C2 119.96(16) . 3_565 ?
C3 C4 C2 121.58(16) . 3_565 ?
C1 O1 Ca1 136.29(11) . . ?
Ca1 O3 H3 118.1 . . ?
Ca1 O4 Ca1 93.19(5) 1_455 . ?
Ca1 O4 H4A 113.1 1_455 . ?
Ca1 O4 H4A 113.1 . . ?
Ca1 O4 H4B 113.1 1_455 . ?
Ca1 O4 H4B 113.1 . . ?
H4A O4 H4B 110.5 . . ?
Ca1 O5 Ca1 99.05(7) . 1_655 ?
Ca1 O5 H5 119.7 . . ?
Ca1 O5 H5 110.0 1_655 . ?

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 C4 50.1(2) . . . 3_565 ?
O2 C1 C2 C4 -128.63(18) . . . 3_565 ?
O1 C1 C2 C3 -130.58(18) . . . . ?
O2 C1 C2 C3 50.7(2) . . . . ?
C4 C2 C3 F1 -178.98(15) 3_565 . . . ?
C1 C2 C3 F1 1.6(3) . . . . ?
C4 C2 C3 C4 -0.7(3) 3_565 . . . ?
C1 C2 C3 C4 179.88(17) . . . . ?
F1 C3 C4 F2 1.2(3) . . . . ?
C2 C3 C4 F2 -177.10(15) . . . . ?
F1 C3 C4 C2 179.05(16) . . . 3_565 ?
C2 C3 C4 C2 0.8(3) . . . 3_565 ?
O2 C1 O1 Ca1 5.7(3) . . . . ?
C2 C1 O1 Ca1 -172.82(11) . . . . ?
O3 Ca1 O1 C1 148.12(16) . . . . ?
O5 Ca1 O1 C1 -86.38(17) . . . . ?
O5 Ca1 O1 C1 19.77(16) 1_455 . . . ?
O4 Ca1 O1 C1 -122.49(16) 4_675 . . . ?
O4 Ca1 O1 C1 -162.06(17) 1_655 . . . ?
O4 Ca1 O1 C1 55.26(18) 4_575 . . . ?
O4 Ca1 O1 C1 93.76(17) . . . . ?
O1 Ca1 O1 C1 -34.9(2) 4_575 . . . ?
Ca1 Ca1 O1 C1 56.38(16) 1_455 . . . ?
Ca1 Ca1 O1 C1 -123.62(16) 1_655 . . . ?
O3 Ca1 O4 Ca1 111.32(5) . . . 1_455 ?
O5 Ca1 O4 Ca1 -117.41(7) . . . 1_455 ?
O5 Ca1 O4 Ca1 -38.03(4) 1_455 . . 1_455 ?
O4 Ca1 O4 Ca1 109.39(7) 4_675 . . 1_455 ?
O4 Ca1 O4 Ca1 180.0 1_655 . . 1_455 ?
O4 Ca1 O4 Ca1 35.01(5) 4_575 . . 1_455 ?
O1 Ca1 O4 Ca1 -117.20(5) . . . 1_455 ?
O1 Ca1 O4 Ca1 -1.65(8) 4_575 . . 1_455 ?
Ca1 Ca1 O4 Ca1 180.0 1_655 . . 1_455 ?
O3 Ca1 O5 Ca1 0.0 . . . 1_655 ?
O5 Ca1 O5 Ca1 180.0 1_455 . . 1_655 ?
O4 Ca1 O5 Ca1 40.94(3) 4_675 . . 1_655 ?
O4 Ca1 O5 Ca1 -40.94(3) 1_655 . . 1_655 ?
O4 Ca1 O5 Ca1 111.57(6) 4_575 . . 1_655 ?
O4 Ca1 O5 Ca1 -111.57(6) . . . 1_655 ?
O1 Ca1 O5 Ca1 -111.78(3) . . . 1_655 ?
O1 Ca1 O5 Ca1 111.78(3) 4_575 . . 1_655 ?
Ca1 Ca1 O5 Ca1 180.0 1_455 . . 1_655 ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.070

_database_code_depnum_ccdc_archive 'CCDC 1003030'
