data_mp2
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          
 'C15 H20 O4'
_chemical_formula_sum
 'C15 H20 O4'
_chemical_formula_weight          264.31
_chemical_absolute_configuration  syn
 
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'

_symmetry_cell_setting           'Orthorhombic'
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1)'
_symmetry_space_group_name_Hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 
_cell_length_a                    4.7285(2)
_cell_length_b                    10.6501(4)
_cell_length_c                    27.8949(12)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1404.76(10)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     3534
_cell_measurement_theta_min       4.15
_cell_measurement_theta_max       65.61
 
_exptl_crystal_description       'plate'
_exptl_crystal_colour             'colourless'
_exptl_crystal_size_max           0.45
_exptl_crystal_size_mid           0.13
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.250
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              568
_exptl_absorpt_coefficient_mu     0.734
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.7331
_exptl_absorpt_correction_T_max   0.9670
_exptl_absorpt_process_details    'sadabs 2008/2'
 
_exptl_special_details
;
Collected, solved and refined by Dr. Zoe R. Turner (Princeton)
;
 
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             3640
_diffrn_reflns_av_R_equivalents   0.0255
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_limit_h_min        -3
_diffrn_reflns_limit_h_max        5
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          4.44
_diffrn_reflns_theta_max          66.07
_reflns_number_total              2101
_reflns_number_gt                 2050
_reflns_threshold_expression      >2\s(I)
 
_computing_data_collection        'BRUKER, APEX II SOFTWARE SUITE'
_computing_cell_refinement        'BRUKER, APEX II SOFTWARE SUITE'
_computing_data_reduction         'BRUKER, APEX II SOFTWARE SUITE'
_computing_structure_solution     'SIR-92 (Giacovazzo, 1994)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'

 
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0467P)^2^+0.1514P] where P=(Fo^2^+2Fc^2^)/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_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881, 1526 Friedel pairs/'
_refine_ls_abs_structure_Flack    -0.05(19)
_refine_ls_number_reflns          2101
_refine_ls_number_parameters      174
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0342
_refine_ls_R_factor_gt            0.0334
_refine_ls_wR_factor_ref          0.0845
_refine_ls_wR_factor_gt           0.0841
_refine_ls_goodness_of_fit_ref    1.071
_refine_ls_restrained_S_all       1.071
_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
C1 C 0.8163(5) 1.2263(2) 0.62921(7) 0.0396(5) Uani 1 1 d . . .
H1A H 0.9648 1.1719 0.6390 0.048 Uiso 1 1 calc R . .
H1B H 0.8277 1.3137 0.6358 0.048 Uiso 1 1 calc R . .
C2 C 0.5953(4) 1.18062(16) 0.60663(6) 0.0275(4) Uani 1 1 d . . .
H2A H 0.4513 1.2380 0.5974 0.033 Uiso 1 1 calc R . .
C3 C 0.5528(4) 1.04485(15) 0.59424(6) 0.0251(4) Uani 1 1 d . . .
H3A H 0.4263 1.0063 0.6184 0.030 Uiso 1 1 calc R . .
H3B H 0.7373 1.0012 0.5960 0.030 Uiso 1 1 calc R . .
C4 C 0.4266(3) 1.02461(14) 0.54460(6) 0.0207(3) Uani 1 1 d . . .
H4 H 0.2465 1.0736 0.5428 0.025 Uiso 1 1 calc R . .
C5 C 0.6093(4) 1.06284(13) 0.50188(6) 0.0198(3) Uani 1 1 d . . .
H5 H 0.8061 1.0309 0.5067 0.024 Uiso 1 1 calc R . .
C6 C 0.4704(3) 0.99111(14) 0.46098(6) 0.0201(3) Uani 1 1 d . . .
H6 H 0.2963 1.0365 0.4503 0.024 Uiso 1 1 calc R . .
C7 C 0.6587(4) 0.96764(14) 0.41864(6) 0.0233(4) Uani 1 1 d . . .
H7A H 0.7384 1.0478 0.4068 0.028 Uiso 1 1 calc R . .
H7B H 0.8170 0.9118 0.4279 0.028 Uiso 1 1 calc R . .
C8 C 0.6574(4) 0.87862(18) 0.34091(6) 0.0332(4) Uani 1 1 d . . .
H8A H 0.8212 0.8260 0.3502 0.040 Uiso 1 1 calc R . .
H8B H 0.7287 0.9557 0.3252 0.040 Uiso 1 1 calc R . .
C9 C 0.4671(4) 0.80767(16) 0.30746(6) 0.0274(4) Uani 1 1 d . . .
C10 C 0.3866(4) 0.68577(18) 0.31884(7) 0.0340(4) Uani 1 1 d . . .
H10 H 0.4584 0.6472 0.3470 0.041 Uiso 1 1 calc R . .
C11 C 0.2038(5) 0.62037(18) 0.28962(7) 0.0396(5) Uani 1 1 d . . .
H11 H 0.1488 0.5374 0.2980 0.048 Uiso 1 1 calc R . .
C12 C 0.0993(5) 0.67493(19) 0.24805(7) 0.0388(5) Uani 1 1 d . . .
H12 H -0.0262 0.6296 0.2279 0.047 Uiso 1 1 calc R . .
C13 C 0.1798(5) 0.79567(19) 0.23636(7) 0.0385(5) Uani 1 1 d . . .
H13 H 0.1100 0.8337 0.2079 0.046 Uiso 1 1 calc R . .
C14 C 0.3622(4) 0.86157(16) 0.26602(6) 0.0327(4) Uani 1 1 d . . .
H14 H 0.4158 0.9448 0.2578 0.039 Uiso 1 1 calc R . .
C15 C 0.3565(4) 0.88745(14) 0.53347(6) 0.0213(3) Uani 1 1 d . . .
H15 H 0.4896 0.8306 0.5510 0.026 Uiso 1 1 calc R . .
O1 O 0.6184(3) 1.19407(9) 0.49246(4) 0.0233(3) Uani 1 1 d . . .
H1 H 0.4564 1.2249 0.4963 0.035 Uiso 1 1 calc R . .
O2 O 0.0789(2) 0.86201(10) 0.54705(4) 0.0243(3) Uani 1 1 d . . .
H2 H 0.0442 0.7855 0.5427 0.037 Uiso 1 1 calc R . .
O3 O 0.3926(3) 0.87277(9) 0.48227(4) 0.0237(3) Uani 1 1 d . . .
O4 O 0.4935(3) 0.91028(10) 0.38229(4) 0.0263(3) Uani 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
C1 0.0406(11) 0.0461(11) 0.0321(11) -0.0067(8) 0.0048(8) -0.0147(9)
C2 0.0265(9) 0.0312(9) 0.0248(9) -0.0036(7) 0.0040(7) -0.0033(7)
C3 0.0236(9) 0.0262(8) 0.0255(9) 0.0002(6) -0.0004(7) 0.0012(7)
C4 0.0183(8) 0.0181(8) 0.0257(9) -0.0003(6) -0.0007(6) -0.0001(6)
C5 0.0181(8) 0.0145(7) 0.0268(9) 0.0008(6) -0.0015(7) 0.0008(6)
C6 0.0182(8) 0.0164(7) 0.0257(9) 0.0006(6) -0.0004(6) -0.0003(6)
C7 0.0193(8) 0.0219(8) 0.0288(9) -0.0011(6) 0.0016(7) -0.0029(7)
C8 0.0288(10) 0.0412(10) 0.0297(10) -0.0065(8) 0.0068(7) -0.0044(9)
C9 0.0257(9) 0.0312(9) 0.0252(9) -0.0052(7) 0.0085(7) -0.0008(7)
C10 0.0391(11) 0.0332(9) 0.0299(10) 0.0026(7) 0.0039(8) -0.0009(8)
C11 0.0461(12) 0.0310(10) 0.0418(11) -0.0053(8) 0.0058(9) -0.0073(9)
C12 0.0351(11) 0.0464(11) 0.0349(11) -0.0156(8) 0.0014(9) -0.0038(9)
C13 0.0407(12) 0.0468(11) 0.0279(10) -0.0033(8) -0.0028(8) 0.0090(9)
C14 0.0385(11) 0.0280(8) 0.0314(10) 0.0004(7) 0.0064(8) 0.0018(8)
C15 0.0188(8) 0.0200(7) 0.0250(8) -0.0009(6) 0.0016(6) 0.0019(7)
O1 0.0232(6) 0.0148(5) 0.0317(6) 0.0007(4) 0.0000(5) -0.0004(4)
O2 0.0204(6) 0.0183(5) 0.0344(7) -0.0014(5) 0.0040(5) -0.0028(4)
O3 0.0292(6) 0.0164(5) 0.0255(6) -0.0010(4) 0.0021(5) -0.0035(5)
O4 0.0238(6) 0.0303(6) 0.0247(6) -0.0057(5) 0.0033(5) -0.0039(5)
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.313(3) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C2 C3 1.500(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.523(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(2) . ?
C4 C15 1.530(2) . ?
C4 H4 1.0000 . ?
C5 O1 1.4228(17) . ?
C5 C6 1.522(2) . ?
C5 H5 1.0000 . ?
C6 O3 1.4410(19) . ?
C6 C7 1.500(2) . ?
C6 H6 1.0000 . ?
C7 O4 1.418(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O4 1.431(2) . ?
C8 C9 1.500(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.383(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O2 1.393(2) . ?
C15 O3 1.447(2) . ?
C15 H15 1.0000 . ?
O1 H1 0.8400 . ?
O2 H2 0.8400 . ?
 
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 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C1 C2 C3 125.03(18) . . ?
C1 C2 H2A 117.5 . . ?
C3 C2 H2A 117.5 . . ?
C2 C3 C4 113.48(14) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 C5 116.74(13) . . ?
C3 C4 C15 113.87(13) . . ?
C5 C4 C15 102.62(12) . . ?
C3 C4 H4 107.7 . . ?
C5 C4 H4 107.7 . . ?
C15 C4 H4 107.7 . . ?
O1 C5 C6 111.57(12) . . ?
O1 C5 C4 115.02(13) . . ?
C6 C5 C4 101.94(12) . . ?
O1 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
O3 C6 C7 109.29(12) . . ?
O3 C6 C5 103.91(12) . . ?
C7 C6 C5 114.69(14) . . ?
O3 C6 H6 109.6 . . ?
C7 C6 H6 109.6 . . ?
C5 C6 H6 109.6 . . ?
O4 C7 C6 107.93(13) . . ?
O4 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
O4 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O4 C8 C9 107.20(14) . . ?
O4 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
C14 C9 C10 118.72(17) . . ?
C14 C9 C8 121.74(16) . . ?
C10 C9 C8 119.52(17) . . ?
C11 C10 C9 120.61(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.40(19) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.31(19) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.14(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.81(17) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
O2 C15 O3 111.00(13) . . ?
O2 C15 C4 109.55(13) . . ?
O3 C15 C4 106.15(12) . . ?
O2 C15 H15 110.0 . . ?
O3 C15 H15 110.0 . . ?
C4 C15 H15 110.0 . . ?
C5 O1 H1 109.5 . . ?
C15 O2 H2 109.5 . . ?
C6 O3 C15 110.02(11) . . ?
C7 O4 C8 112.33(13) . . ?
 
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
C1 C2 C3 C4 -139.52(19) . . . . ?
C2 C3 C4 C5 66.07(19) . . . . ?
C2 C3 C4 C15 -174.56(14) . . . . ?
C3 C4 C5 O1 -77.64(17) . . . . ?
C15 C4 C5 O1 157.11(13) . . . . ?
C3 C4 C5 C6 161.47(13) . . . . ?
C15 C4 C5 C6 36.22(15) . . . . ?
O1 C5 C6 O3 -161.20(12) . . . . ?
C4 C5 C6 O3 -37.95(15) . . . . ?
O1 C5 C6 C7 79.56(17) . . . . ?
C4 C5 C6 C7 -157.18(13) . . . . ?
O3 C6 C7 O4 68.81(16) . . . . ?
C5 C6 C7 O4 -175.01(12) . . . . ?
O4 C8 C9 C14 106.20(18) . . . . ?
O4 C8 C9 C10 -71.9(2) . . . . ?
C14 C9 C10 C11 -0.6(3) . . . . ?
C8 C9 C10 C11 177.58(18) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C8 C9 C14 C13 -178.01(17) . . . . ?
C12 C13 C14 C9 0.3(3) . . . . ?
C3 C4 C15 O2 90.94(16) . . . . ?
C5 C4 C15 O2 -141.95(13) . . . . ?
C3 C4 C15 O3 -149.14(13) . . . . ?
C5 C4 C15 O3 -22.03(16) . . . . ?
C7 C6 O3 C15 148.00(13) . . . . ?
C5 C6 O3 C15 25.15(16) . . . . ?
O2 C15 O3 C6 117.15(13) . . . . ?
C4 C15 O3 C6 -1.82(17) . . . . ?
C6 C7 O4 C8 -177.32(13) . . . . ?
C9 C8 O4 C7 174.44(14) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.933
_diffrn_reflns_theta_full              66.07
_diffrn_measured_fraction_theta_full   0.932
_refine_diff_density_max    0.145
_refine_diff_density_min   -0.215
_refine_diff_density_rms    0.046