#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2003242.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003242
loop_
_publ_author_name
'Capron, M. A.'
'An, J.'
'Swenson, D. C.'
'Wiemer, D. F.'
_publ_section_title
;
 Cyclic (1<i>R</i>,3<i>R</i>)-1,3-Dimethyltrimethylene
 [(5<i>R</i>)-2-Hydroxy-5-methyl-5-(2-methyl-1,3-dioxolan-2-yl)-1-cyclohexen-1-yl]phosphonate,
 a Stable Enol
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              479
_journal_page_last               482
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C16 H27 O6 P1'
_chemical_formula_sum            'C16 H27 O6 P'
_chemical_formula_weight         346.36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source           'Cromer & Waber (1974)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.677(7)
_cell_length_b                   16.763(8)
_cell_length_c                   10.015(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     1792.5(17)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    MolEN
_computing_publication_material  MolEN
_computing_structure_refinement  MolEN
_computing_structure_solution    MolEN
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q-2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4495
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        <0.3
_diffrn_standards_interval_count
;
500 reflections (for orientation) and every 240 min
(for intensity)
;
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    0.17
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.28
_exptl_crystal_description       'irregular platelet'
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.187
_refine_ls_goodness_of_fit_obs   1.09
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1274
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'calc w = 1/[\s^2^(F) + (0.06F)^2^]'
_refine_ls_wR_factor_obs         0.048
_reflns_number_observed          1274
_reflns_number_total             1804
_reflns_observed_criterion       I>2\s
_[local]_cod_data_source_file    bk1079.cif
_[local]_cod_data_source_block   capron2
_[local]_cod_chemical_formula_sum_orig 'C16 H27 O6 P1'
_cod_original_cell_volume        1793(3)
_cod_database_code               2003242
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
P(1) 0.0348(4) 0.0582(5) 0.0480(4) -0.0009(5) 0.0015(4) -0.0136(5)
O(1) 0.071(2) 0.0450(10) 0.085(2) 0.0110(10) 0.007(2) 0.0070(10)
O(2) 0.0520(10) 0.0650(10) 0.086(2) 0.0080(10) 0.009(2) -0.024(2)
O(3) 0.0490(10) 0.090(2) 0.0470(10) -0.0160(10) 0.0060(10) 0.0010(10)
O(4) 0.0390(10) 0.078(2) 0.061(2) -0.0040(10) 0.0050(10) -0.0240(10)
O(5) 0.0570(10) 0.0480(10) 0.053(2) 0.0040(10) -0.0150(10) 0.0000(10)
O(6) 0.0590(10) 0.0390(10) 0.0560(10) -0.0070(10) -0.0030(10) 0.0010(10)
C(1) 0.046(2) 0.045(2) 0.048(2) 0.008(2) -0.007(2) 0.001(2)
C(2) 0.037(2) 0.046(2) 0.043(2) 0.004(2) -0.001(2) -0.002(2)
C(3) 0.038(2) 0.045(2) 0.048(2) -0.003(2) 0.004(2) 0.000(2)
C(4) 0.034(2) 0.043(2) 0.039(2) -0.006(2) 0.002(2) 0.006(2)
C(5) 0.041(2) 0.048(2) 0.055(2) -0.009(2) 0.002(2) 0.008(2)
C(6) 0.057(2) 0.045(2) 0.055(2) -0.008(2) 0.003(2) 0.008(2)
C(7) 0.061(2) 0.070(2) 0.046(2) 0.001(2) -0.007(2) 0.002(2)
C(8) 0.044(2) 0.045(2) 0.043(2) -0.002(2) 0.006(2) -0.004(2)
C(9) 0.053(2) 0.062(2) 0.076(3) 0.007(2) 0.014(2) -0.001(2)
C(21) 0.066(2) 0.077(3) 0.064(3) -0.002(2) 0.016(2) 0.004(2)
C(22) 0.081(3) 0.061(2) 0.123(4) -0.014(2) 0.028(3) -0.012(3)
C(23) 0.051(2) 0.084(3) 0.083(3) -0.022(2) 0.015(2) -0.037(2)
C(24) 0.147(6) 0.144(5) 0.142(5) -0.019(5) -0.005(5) 0.079(4)
C(25) 0.041(2) 0.117(3) 0.119(4) -0.007(3) 0.019(3) -0.039(3)
C(31) 0.153(5) 0.049(2) 0.072(3) 0.013(3) -0.037(3) 0.006(2)
C(32) 0.111(4) 0.068(2) 0.091(3) -0.015(3) -0.006(4) 0.035(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
P(1) 0.40304(8) 0.99431(6) 0.68480(10) 0.0470(2) Uani ? ? P
O(1) 0.5369(3) 1.1316(2) 0.5460(3) 0.0667(9) Uani ? ? O
O(2) 0.3551(3) 1.0766(2) 0.6973(3) 0.0674(8) Uani ? ? O
O(3) 0.4340(2) 0.9525(2) 0.8221(3) 0.0618(8) Uani ? ? O
O(4) 0.3094(2) 0.9365(2) 0.6120(3) 0.0598(8) Uani ? ? O
O(5) 0.8547(2) 0.84750(10) 0.6444(3) 0.0528(8) Uani ? ? O
O(6) 0.7325(3) 0.76660(10) 0.5160(3) 0.0516(6) Uani ? ? O
C(1) 0.5903(3) 1.0585(2) 0.5400(4) 0.0462(9) Uani ? ? C
C(2) 0.5447(3) 0.9907(2) 0.5947(3) 0.0423(9) Uani ? ? C
C(3) 0.6115(3) 0.9114(2) 0.5849(4) 0.0438(9) Uani ? ? C
C(4) 0.7177(3) 0.9085(2) 0.4814(3) 0.0388(9) Uani ? ? C
C(5) 0.7917(3) 0.9871(2) 0.4891(4) 0.0480(9) Uani ? ? C
C(6) 0.7112(4) 1.0599(2) 0.4641(4) 0.0520(10) Uani ? ? C
C(7) 0.6609(4) 0.8985(2) 0.3418(4) 0.0590(10) Uani ? ? C
C(8) 0.8058(4) 0.8388(2) 0.5126(4) 0.0441(9) Uani ? ? C
C(9) 0.9142(4) 0.8285(3) 0.4161(5) 0.0630(10) Uani ? ? C
C(21) 0.3467(4) 0.9047(3) 0.8969(5) 0.0680(10) Uani ? ? C
C(22) 0.2709(4) 0.8519(3) 0.8040(6) 0.0890(10) Uani ? ? C
C(23) 0.2117(4) 0.8959(3) 0.6891(5) 0.0720(10) Uani ? ? C
C(24) 0.4218(7) 0.8590(4) 0.9952(7) 0.144(2) Uani ? ? C
C(25) 0.1109(4) 0.9518(3) 0.7309(6) 0.0920(10) Uani ? ? C
C(31) 0.8497(6) 0.7732(3) 0.7101(5) 0.0910(10) Uani ? ? C
C(32) 0.7779(6) 0.7204(3) 0.6224(6) 0.0900(10) Uani ? ? C
H(O1) 0.474(3) 0.124(2) 0.578(4) 0.070(10) Uiso ? ? H
H(7B) 0.6213 0.8477 0.3355 0.08 Uiso calc C7 H
H(7C) 0.6005 0.9394 0.3266 0.08 Uiso calc C7 H
H(7A) 0.7253 0.9020 0.2764 0.08 Uiso calc C7 H
H(9B) 0.8827 0.8170 0.3293 0.08 Uiso calc C9 H
H(9C) 0.9623 0.8763 0.4133 0.08 Uiso calc C9 H
H(9A) 0.9659 0.7855 0.4452 0.08 Uiso calc C9 H
H(24A) 0.3674 0.8261 1.0470 0.2 Uiso calc C24 H
H(24C) 0.4647 0.8950 1.0524 0.2 Uiso calc C24 H
H(24B) 0.4807 0.8264 0.9493 0.2 Uiso calc C24 H
H(25A) 0.0888 0.9852 0.6579 0.1 Uiso calc C25 H
H(25B) 0.1398 0.9837 0.8034 0.1 Uiso calc C25 H
H(25C) 0.0393 0.9221 0.7583 0.1 Uiso calc C25 H
H(3A) 0.5514 0.8718 0.5618 0.05 Uiso calc C3 H
H(3B) 0.6462 0.8995 0.6702 0.05 Uiso calc C3 H
H(5A) 0.8565 0.9857 0.4238 0.05 Uiso calc C5 H
H(5B) 0.8277 0.9914 0.5757 0.05 Uiso calc C5 H
H(6A) 0.7570 1.1060 0.4900 0.06 Uiso calc C6 H
H(6B) 0.6926 1.0627 0.3712 0.06 Uiso calc C6 H
H(21) 0.2865 0.9364 0.9425 0.09 Uiso calc C21 H
H(22A) 0.2060 0.8273 0.8546 0.1 Uiso calc C22 H
H(22B) 0.3248 0.8119 0.7687 0.1 Uiso calc C22 H
H(23) 0.1711 0.8575 0.6338 0.09 Uiso calc C23 H
H(31A) 0.8092 0.7785 0.7942 0.1 Uiso calc C31 H
H(31B) 0.9321 0.7528 0.7230 0.1 Uiso calc C31 H
H(32A) 0.8303 0.6789 0.5892 0.1 Uiso calc C32 H
H(32B) 0.7097 0.6975 0.6704 0.1 Uiso calc C32 H
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O(2) P(1) O(3) 114.4(2) yes
O(2) P(1) O(4) 113.3(2) yes
O(2) P(1) C(2) 111.9(2) yes
O(3) P(1) O(4) 105.3(2) yes
O(3) P(1) C(2) 104.5(2) yes
O(4) P(1) C(2) 106.7(2) yes
P(1) O(3) C(21) 124.4(3) yes
P(1) O(4) C(23) 119.7(3) yes
C(8) O(5) C(31) 109.1(3) yes
C(8) O(6) C(32) 107.1(4) yes
O(1) C(1) C(2) 126.3(4) yes
O(1) C(1) C(6) 111.8(4) yes
C(2) C(1) C(6) 121.9(4) yes
P(1) C(2) C(1) 119.1(3) yes
P(1) C(2) C(3) 118.0(3) yes
C(1) C(2) C(3) 122.9(3) yes
C(2) C(3) C(4) 114.8(3) yes
C(3) C(4) C(5) 108.5(3) yes
C(3) C(4) C(7) 109.1(3) yes
C(3) C(4) C(8) 109.8(3) yes
C(5) C(4) C(7) 110.1(3) yes
C(7) C(4) C(8) 110.2(3) yes
C(4) C(5) C(6) 113.0(3) yes
C(1) C(6) C(5) 113.1(3) yes
O(5) C(8) O(6) 105.3(3) yes
O(5) C(8) C(4) 109.6(3) yes
O(5) C(8) C(9) 108.7(4) yes
O(6) C(8) C(4) 108.1(3) yes
O(6) C(8) C(9) 109.5(3) yes
C(4) C(8) C(9) 115.1(4) yes
O(3) C(21) C(22) 110.6(5) yes
O(3) C(21) C(24) 106.5(5) yes
C(22) C(21) C(24) 113.2(6) yes
C(21) C(22) C(23) 113.9(4) yes
O(4) C(23) C(22) 109.4(4) yes
O(4) C(23) C(25) 111.8(4) yes
C(22) C(23) C(25) 113.4(5) yes
O(5) C(31) C(32) 105.9(4) yes
O(6) C(32) C(31) 107.6(4) yes
C(1) O(1) H(O1) 104(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P(1) O(2) 1.477(3) yes
P(1) O(3) 1.579(3) yes
P(1) O(4) 1.571(3) yes
P(1) C(2) 1.762(4) yes
O(1) C(1) 1.352(5) yes
O(3) C(21) 1.440(6) yes
O(4) C(23) 1.466(6) yes
O(5) C(8) 1.427(5) yes
O(5) C(31) 1.410(6) yes
O(6) C(8) 1.441(5) yes
O(6) C(32) 1.405(7) yes
C(1) C(2) 1.352(5) yes
C(1) C(6) 1.498(6) yes
C(2) C(3) 1.511(6) yes
C(3) C(4) 1.538(5) yes
C(4) C(5) 1.537(5) yes
C(4) C(7) 1.533(6) yes
C(4) C(8) 1.533(5) yes
C(5) C(6) 1.513(6) yes
C(8) C(9) 1.518(6) yes
C(21) C(22) 1.518(8) yes
C(21) C(24) 1.483(9) yes
C(22) C(23) 1.507(9) yes
C(23) C(25) 1.486(7) yes
C(31) C(32) 1.464(8) yes
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
O(2) P(1) O(3) C(21) 91.4(3)
O(4) P(1) O(3) C(21) -33.6(3)
C(2) P(1) O(3) C(21) -145.8(3)
O(2) P(1) O(4) C(23) -86.2(3)
O(3) P(1) O(4) C(23) 39.5(3)
C(2) P(1) O(4) C(23) 150.2(3)
O(2) P(1) C(2) C(1) -4.3(4)
O(2) P(1) C(2) C(3) 174.3(3)
O(3) P(1) C(2) C(1) -128.6(3)
O(3) P(1) C(2) C(3) 49.9(3)
O(4) P(1) C(2) C(1) 120.1(3)
O(4) P(1) C(2) C(3) -61.3(3)
P(1) O(3) C(21) C(22) 40.7(5)
P(1) O(3) C(21) C(24) 164.1(3)
P(1) O(4) C(23) C(22) -53.9(4)
P(1) O(4) C(23) C(25) 72.6(4)
C(31) O(5) C(8) O(6) 19.5(4)
C(31) O(5) C(8) C(4) 135.6(4)
C(31) O(5) C(8) C(9) -97.7(4)
C(8) O(5) C(31) C(32) -8.6(5)
C(32) O(6) C(8) O(5) -23.0(4)
C(32) O(6) C(8) C(4) -140.1(3)
C(32) O(6) C(8) C(9) 93.7(4)
O(1) C(1) C(2) P(1) -0.6(5)
O(1) C(1) C(2) C(3) -179.1(3)
C(6) C(1) C(2) P(1) 179.0(3)
C(6) C(1) C(2) C(3) 0.5(6)
O(1) C(1) C(6) C(5) 163.0(3)
C(2) C(1) C(6) C(5) -16.6(5)
P(1) C(2) C(3) C(4) 167.5(2)
C(1) C(2) C(3) C(4) -14.0(5)
C(2) C(3) C(4) C(5) 41.2(4)
C(2) C(3) C(4) C(7) -78.7(4)
C(2) C(3) C(4) C(8) 160.5(3)
C(3) C(4) C(5) C(6) -58.4(4)
C(7) C(4) C(5) C(6) 60.9(4)
C(8) C(4) C(5) C(6) -178.1(3)
C(3) C(4) C(8) O(5) -57.9(4)
C(3) C(4) C(8) O(6) 56.3(4)
C(3) C(4) C(8) C(9) 179.1(3)
C(5) C(4) C(8) O(5) 60.9(4)
C(5) C(4) C(8) O(6) 175.2(3)
C(5) C(4) C(8) C(9) -62.0(4)
C(7) C(4) C(8) O(5) -178.1(3)
C(7) C(4) C(8) O(6) -63.8(4)
C(7) C(4) C(8) C(9) 59.0(4)
C(4) C(5) C(6) C(1) 46.4(4)
O(3) C(21) C(22) C(23) -50.7(5)
C(24) C(21) C(22) C(23) -170.1(5)
C(21) C(22) C(23) O(4) 57.6(5)
C(21) C(22) C(23) C(25) -68.0(5)
O(5) C(31) C(32) O(6) -5.9(6)