 
data_n2
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H26 O3'
_chemical_formula_weight          302.40
 
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'
 
_symmetry_cell_setting            ?
_symmetry_space_group_name_H-M    ?
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.032(2)
_cell_length_b                    18.500(4)
_cell_length_c                    9.118(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.47(3)
_cell_angle_gamma                 90.00
_cell_volume                      1595.5(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.259
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              656
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             12534
_diffrn_reflns_av_R_equivalents   0.1040
_diffrn_reflns_av_sigmaI/netI     0.0745
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -24
_diffrn_reflns_limit_k_max        24
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.42
_diffrn_reflns_theta_max          28.19
_reflns_number_total              3783
_reflns_number_gt                 2485
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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)+(0.0694P)²+0.0063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0019(19)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3783
_refine_ls_number_parameters      204
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0709
_refine_ls_R_factor_gt            0.0456
_refine_ls_wR_factor_ref          0.1341
_refine_ls_wR_factor_gt           0.1225
_refine_ls_goodness_of_fit_ref    1.029
_refine_ls_restrained_S_all       1.029
_refine_ls_shift/su_max           0.009
_refine_ls_shift/su_mean          0.002
 
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 -0.31206(15) 0.08848(8) -0.19977(18) 0.0443(3) Uani 1 1 d . . .
H1A H -0.3509 0.1351 -0.2414 0.0577(10) Uiso 1 1 calc R . .
H1B H -0.3248 0.0558 -0.2865 0.0577(10) Uiso 1 1 calc R . .
C1A C -0.15486(14) 0.09664(6) -0.11005(15) 0.0326(3) Uani 1 1 d . . .
HC1A H -0.1208 0.0482 -0.0723 0.0577(10) Uiso 1 1 calc R . .
C2 C -0.39118(17) 0.05956(9) -0.0967(2) 0.0553(4) Uani 1 1 d . . .
H2A H -0.3596 0.0107 -0.0647 0.0577(10) Uiso 1 1 calc R . .
H2B H -0.4914 0.0577 -0.1556 0.0577(10) Uiso 1 1 calc R . .
C3 C -0.36802(16) 0.10612(9) 0.0465(2) 0.0513(4) Uani 1 1 d . . .
H3A H -0.4149 0.0842 0.1128 0.0577(10) Uiso 1 1 calc R . .
H3B H -0.4096 0.1534 0.0153 0.0577(10) Uiso 1 1 calc R . .
C4 C -0.21122(15) 0.11457(8) 0.13730(17) 0.0421(3) Uani 1 1 d . . .
H4A H -0.1993 0.1474 0.2237 0.0577(10) Uiso 1 1 calc R . .
H4B H -0.1723 0.0681 0.1795 0.0577(10) Uiso 1 1 calc R . .
C4A C -0.13127(13) 0.14339(6) 0.03560(15) 0.0321(3) Uani 1 1 d . . .
O4A O -0.17701(10) 0.21472(5) -0.01551(11) 0.0372(2) Uani 1 1 d . . .
HO4A H -0.1535 0.2423 0.0591 0.067(4) Uiso 1 1 calc R . .
O5 O 0.01311(9) 0.14393(5) 0.12862(10) 0.0351(2) Uani 1 1 d . . .
C6 C 0.10827(14) 0.16894(7) 0.05178(15) 0.0339(3) Uani 1 1 d . . .
H6 H 0.0849 0.2193 0.0199 0.0577(10) Uiso 1 1 calc R . .
C6A C 0.09282(14) 0.12353(6) -0.09391(15) 0.0337(3) Uani 1 1 d . . .
HC6A H 0.1183 0.0737 -0.0593 0.0577(10) Uiso 1 1 calc R . .
C7 C 0.19233(18) 0.14770(8) -0.17894(19) 0.0483(4) Uani 1 1 d . . .
H7A H 0.1726 0.1977 -0.2110 0.0577(10) Uiso 1 1 calc R . .
H7B H 0.2891 0.1449 -0.1088 0.0577(10) Uiso 1 1 calc R . .
C8 C 0.17604(19) 0.10105(9) -0.3211(2) 0.0535(4) Uani 1 1 d . . .
H8A H 0.2359 0.1199 -0.3765 0.0577(10) Uiso 1 1 calc R . .
H8B H 0.2069 0.0522 -0.2880 0.0577(10) Uiso 1 1 calc R . .
C9 C 0.02520(19) 0.09933(8) -0.42873(18) 0.0516(4) Uani 1 1 d . . .
H9A H 0.0173 0.0664 -0.5140 0.0577(10) Uiso 1 1 calc R . .
H9B H -0.0020 0.1471 -0.4721 0.0577(10) Uiso 1 1 calc R . .
C10 C -0.07448(17) 0.07525(7) -0.34393(16) 0.0427(3) Uani 1 1 d . . .
H10A H -0.0534 0.0256 -0.3101 0.0577(10) Uiso 1 1 calc R . .
H10B H -0.1710 0.0769 -0.4152 0.0577(10) Uiso 1 1 calc R . .
C10A C -0.06216(14) 0.12254(6) -0.20320(14) 0.0327(3) Uani 1 1 d . . .
O10A O -0.10539(12) 0.19403(5) -0.26385(11) 0.0429(3) Uani 1 1 d . . .
HO10 H -0.1303 0.2172 -0.2008 0.067(4) Uiso 1 1 calc R . .
C11 C 0.25387(14) 0.16683(7) 0.17110(16) 0.0365(3) Uani 1 1 d . . .
C12 C 0.35519(16) 0.21688(8) 0.1674(2) 0.0471(4) Uani 1 1 d . . .
H12 H 0.3331 0.2522 0.0904 0.0577(10) Uiso 1 1 calc R . .
C13 C 0.48901(17) 0.21485(9) 0.2773(2) 0.0565(4) Uani 1 1 d . . .
H13 H 0.5564 0.2486 0.2731 0.0577(10) Uiso 1 1 calc R . .
C14 C 0.52312(17) 0.16374(10) 0.3916(2) 0.0606(5) Uani 1 1 d . . .
H14 H 0.6132 0.1627 0.4654 0.0577(10) Uiso 1 1 calc R . .
C15 C 0.42393(18) 0.11387(10) 0.3973(2) 0.0606(4) Uani 1 1 d . . .
H15 H 0.4467 0.0790 0.4751 0.0577(10) Uiso 1 1 calc R . .
C16 C 0.29005(16) 0.11541(8) 0.28749(18) 0.0482(4) Uani 1 1 d . . .
H16 H 0.2234 0.0813 0.2921 0.0577(10) Uiso 1 1 calc R . .
 
 
_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 C2 1.516(2) . ?
C1 C1A 1.5228(19) . ?
C1A C10A 1.5304(18) . ?
C1A C4A 1.5357(17) . ?
C2 C3 1.516(2) . ?
C3 C4 1.522(2) . ?
C4 C4A 1.5111(19) . ?
C4A O5 1.4136(16) . ?
C4A O4A 1.4235(15) . ?
O5 C6 1.4361(16) . ?
C6 C11 1.5031(19) . ?
C6 C6A 1.5353(18) . ?
C6A C7 1.5211(19) . ?
C6A C10A 1.5420(19) . ?
C7 C8 1.520(2) . ?
C8 C9 1.505(3) . ?
C9 C10 1.520(2) . ?
C10 C10A 1.5236(17) . ?
C10A O10A 1.4435(14) . ?
C11 C16 1.381(2) . ?
C11 C12 1.3836(19) . ?
C12 C13 1.382(2) . ?
C13 C14 1.364(3) . ?
C14 C15 1.371(2) . ?
C15 C16 1.382(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 C1 C1A 111.37(12) . . ?
C1 C1A C10A 116.42(11) . . ?
C1 C1A C4A 110.72(11) . . ?
C10A C1A C4A 110.89(10) . . ?
C1 C2 C3 111.84(13) . . ?
C2 C3 C4 111.15(12) . . ?
C4A C4 C3 111.49(12) . . ?
O5 C4A O4A 110.11(9) . . ?
O5 C4A C4 106.35(10) . . ?
O4A C4A C4 110.42(10) . . ?
O5 C4A C1A 110.77(10) . . ?
O4A C4A C1A 107.40(10) . . ?
C4 C4A C1A 111.82(11) . . ?
C4A O5 C6 115.11(9) . . ?
O5 C6 C11 106.39(10) . . ?
O5 C6 C6A 110.73(10) . . ?
C11 C6 C6A 113.92(11) . . ?
C7 C6A C6 112.70(11) . . ?
C7 C6A C10A 111.46(11) . . ?
C6 C6A C10A 110.79(10) . . ?
C8 C7 C6A 111.44(12) . . ?
C9 C8 C7 111.53(13) . . ?
C8 C9 C10 111.32(13) . . ?
C9 C10 C10A 112.19(12) . . ?
O10A C10A C10 105.89(10) . . ?
O10A C10A C1A 109.81(10) . . ?
C10 C10A C1A 113.20(11) . . ?
O10A C10A C6A 110.25(10) . . ?
C10 C10A C6A 109.41(11) . . ?
C1A C10A C6A 108.26(10) . . ?
C16 C11 C12 118.21(13) . . ?
C16 C11 C6 121.15(12) . . ?
C12 C11 C6 120.63(13) . . ?
C13 C12 C11 120.55(15) . . ?
C14 C13 C12 120.55(15) . . ?
C13 C14 C15 119.69(16) . . ?
C14 C15 C16 120.07(16) . . ?
C11 C16 C15 120.93(14) . . ?
 
_diffrn_measured_fraction_theta_max    0.962
_diffrn_reflns_theta_full              28.19
_diffrn_measured_fraction_theta_full   0.962
_refine_diff_density_max    0.182
_refine_diff_density_min   -0.204
_refine_diff_density_rms    0.042
