#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006670.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_2006670
loop_
_publ_author_name
'Batey, R. A.'
'Lin, D.'
'Lough, A. J.'
_publ_contact_author
;
Alan John Lough
Department of Chemistry
University of Toronto
Toronto
Ontario
Canada, M5S 1A1
;
_publ_section_title
;
(3aR*,4S*,5S*,7aR*)-4-Nitrobenzoic Acid
5-Methyl-1,3,3a,4,5,7a-hexahydroisobenzofuran-4-yl Ester
;
_journal_issue 11
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 1721
_journal_page_last 1723
_journal_volume 53
_journal_year 1997
_chemical_formula_sum 'C16 H17 N O5'
_chemical_formula_weight 303.31
_chemical_name_systematic
;
(3aR*,4S*,5S*,7aR*)-4-nitrobenzoic acid
5-methyl-1,3,3,4,5,7a-hexahydroisobenzofuran-4-yl ester
;
_space_group_IT_number 14
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_audit_creation_method SHELXL
_cell_angle_alpha 90.00
_cell_angle_beta 91.769(7)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 8.0485(9)
_cell_length_b 14.301(2)
_cell_length_c 13.2703(14)
_cell_measurement_reflns_used 43
_cell_measurement_temperature 213(2)
_cell_measurement_theta_max 25.00
_cell_measurement_theta_min 5.25
_cell_volume 1526.7(3)
_computing_cell_refinement XSCANS
_computing_data_collection 'XSCANS (Siemens, 1994)'
_computing_data_reduction XSCANS
_computing_molecular_graphics SHELXTL/PC
_computing_publication_material SHELXTL/PC
_computing_structure_refinement SHELXTL/PC
_computing_structure_solution 'SHELXTL/PC (Sheldrick, 1994)'
_diffrn_ambient_temperature 213(2)
_diffrn_measurement_device 'Siemens P4'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0195
_diffrn_reflns_av_sigmaI/netI 0.0279
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 4686
_diffrn_reflns_theta_max 30.00
_diffrn_reflns_theta_min 2.53
_diffrn_standards_decay_% 'less than 2'
_diffrn_standards_interval_count 97
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.099
_exptl_absorpt_correction_type none
_exptl_crystal_colour 'pale yellow'
_exptl_crystal_density_diffrn 1.320
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description 'flat needle'
_exptl_crystal_F_000 640
_exptl_crystal_size_max 0.49
_exptl_crystal_size_mid 0.45
_exptl_crystal_size_min 0.36
_refine_diff_density_max 0.251
_refine_diff_density_min -0.219
_refine_ls_extinction_coef 0.0027(14)
_refine_ls_extinction_method 'SHELXTL/PC (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_all 1.045
_refine_ls_goodness_of_fit_obs 1.165
_refine_ls_hydrogen_treatment 'H atoms riding'
_refine_ls_matrix_type full
_refine_ls_number_parameters 201
_refine_ls_number_reflns 4405
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.045
_refine_ls_restrained_S_obs 1.165
_refine_ls_R_factor_all 0.0607
_refine_ls_R_factor_obs 0.0433
_refine_ls_shift/esd_max 0.001
_refine_ls_shift/esd_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.0556P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all 0.1288
_refine_ls_wR_factor_obs 0.1212
_reflns_number_observed 3182
_reflns_number_total 4405
_reflns_observed_criterion >2sigma(I)
_[local]_cod_data_source_file fg1329.cif
_[local]_cod_data_source_block s9680
_[local]_cod_cif_authors_sg_H-M 'P 21 / c'
_cod_database_code 2006670
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'
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
O1 0.0468(5) 0.0281(4) 0.0393(4) -0.0037(3) 0.0116(3) -0.0017(3)
O2 0.0999(9) 0.0464(5) 0.0520(6) -0.0146(5) 0.0376(6) -0.0091(4)
O3 0.0349(4) 0.0452(5) 0.0629(6) 0.0018(4) 0.0065(4) -0.0064(4)
O4 0.1040(10) 0.0412(6) 0.1201(11) -0.0132(6) 0.0097(8) -0.0324(7)
O5 0.1069(10) 0.0407(6) 0.0969(10) -0.0165(6) 0.0109(8) 0.0083(6)
C1 0.0475(6) 0.0345(5) 0.0361(6) -0.0017(5) 0.0065(5) -0.0038(4)
C2 0.0376(5) 0.0272(5) 0.0326(5) -0.0037(4) 0.0061(4) 0.0013(4)
C3 0.0329(5) 0.0404(6) 0.0392(6) 0.0001(5) 0.0082(4) 0.0016(5)
C4 0.0338(6) 0.0472(7) 0.0478(6) -0.0116(5) 0.0026(5) 0.0007(5)
C5 0.0426(6) 0.0367(6) 0.0463(6) -0.0139(5) 0.0048(5) -0.0029(5)
C6 0.0385(6) 0.0288(5) 0.0373(5) -0.0042(4) 0.0041(4) 0.0008(4)
C7 0.0314(5) 0.0293(5) 0.0326(5) -0.0044(4) 0.0037(4) 0.0007(4)
C8 0.0348(5) 0.0385(6) 0.0506(7) -0.0042(5) 0.0022(5) -0.0038(5)
C9 0.0437(6) 0.0343(6) 0.0494(7) -0.0002(5) 0.0048(5) -0.0026(5)
C10 0.0453(7) 0.0541(7) 0.0475(7) 0.0075(6) 0.0015(5) 0.0079(6)
C11 0.0378(6) 0.0318(5) 0.0367(5) 0.0014(4) -0.0014(4) -0.0025(4)
C12 0.0498(7) 0.0307(5) 0.0417(6) -0.0004(5) 0.0062(5) -0.0037(4)
C13 0.0483(7) 0.0324(6) 0.0501(7) 0.0004(5) 0.0040(5) 0.0024(5)
C14 0.0396(6) 0.0288(5) 0.0547(7) 0.0020(4) -0.0112(5) -0.0025(5)
C15 0.0492(7) 0.0389(6) 0.0483(7) 0.0061(5) -0.0090(5) -0.0144(5)
C16 0.0473(6) 0.0415(6) 0.0378(6) 0.0021(5) -0.0008(5) -0.0074(5)
N1 0.0550(7) 0.0322(5) 0.0787(9) -0.0012(5) -0.0151(6) -0.0040(6)
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.20941(10) 0.74125(5) 0.42078(6) 0.0378(2) Uani d . 1 O
O2 0.0743(2) 0.77328(7) 0.56236(8) 0.0654(3) Uani d . 1 O
O3 0.52612(10) 0.50303(6) 0.34977(7) 0.0476(2) Uani d . 1 O
O4 0.3387(2) 1.23088(8) 0.51066(12) 0.0883(4) Uani d . 1 O
O5 0.4497(2) 1.19499(8) 0.37049(11) 0.0813(4) Uani d . 1 O
C1 0.1582(2) 0.79776(8) 0.49350(9) 0.0392(3) Uani d . 1 C
C2 0.16110(13) 0.64308(7) 0.42684(8) 0.0324(2) Uani d . 1 C
H2A 0.17212 0.62196 0.49778 0.039 Uiso calc R 1 H
C3 -0.01990(13) 0.62778(8) 0.38804(9) 0.0374(2) Uani d . 1 C
H3A -0.09335 0.64060 0.44490 0.045 Uiso calc R 1 H
C4 -0.04847(15) 0.52714(9) 0.35631(10) 0.0429(3) Uani d . 1 C
H4A -0.15818 0.50961 0.33886 0.051 Uiso calc R 1 H
C5 0.06742(15) 0.46160(8) 0.35097(9) 0.0418(3) Uani d . 1 C
H5A 0.03901 0.40118 0.32852 0.050 Uiso calc R 1 H
C6 0.24373(14) 0.48425(7) 0.38084(9) 0.0348(2) Uani d . 1 C
H6A 0.25883 0.47149 0.45388 0.042 Uiso calc R 1 H
C7 0.27825(12) 0.58793(7) 0.36386(8) 0.0310(2) Uani d . 1 C
H7A 0.25618 0.60299 0.29187 0.037 Uiso calc R 1 H
C8 0.46408(14) 0.59168(8) 0.38599(10) 0.0412(3) Uani d . 1 C
H8A 0.51464 0.64401 0.35040 0.049 Uiso calc R 1 H
H8B 0.48788 0.59867 0.45847 0.049 Uiso calc R 1 H
C9 0.38885(15) 0.44064(8) 0.32773(10) 0.0424(3) Uani d . 1 C
H9A 0.41247 0.37778 0.35384 0.051 Uiso calc R 1 H
H9B 0.36574 0.43667 0.25491 0.051 Uiso calc R 1 H
C10 -0.0716(2) 0.69417(10) 0.30187(10) 0.0490(3) Uani d . 1 C
H10A -0.1834 0.6789 0.2778 0.073 Uiso calc R 1 H
H10B 0.0046 0.6875 0.2471 0.073 Uiso calc R 1 H
H10C -0.0689 0.75815 0.3261 0.073 Uiso calc R 1 H
C11 0.21448(14) 0.89604(8) 0.47835(8) 0.0355(2) Uani d . 1 C
C12 0.2936(2) 0.92342(8) 0.39160(9) 0.0406(3) Uani d . 1 C
H12A 0.3130 0.87940 0.34069 0.049 Uiso calc R 1 H
C13 0.3442(2) 1.01547(8) 0.37970(10) 0.0436(3) Uani d . 1 C
H13A 0.3981 1.03460 0.32134 0.052 Uiso calc R 1 H
C14 0.31311(15) 1.07806(8) 0.45589(10) 0.0413(3) Uani d . 1 C
C15 0.2327(2) 1.05345(9) 0.54211(10) 0.0457(3) Uani d . 1 C
H15A 0.2120 1.09810 0.59216 0.055 Uiso calc R 1 H
C16 0.1832(2) 0.96151(9) 0.55336(9) 0.0422(3) Uani d . 1 C
H16A 0.1285 0.94311 0.61167 0.051 Uiso calc R 1 H
N1 0.3703(2) 1.17553(8) 0.44456(11) 0.0557(3) Uani d . 1 N
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'
N N 0.0061 0.0033 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C1 O1 C2 117.02(8) n
C9 O3 C8 109.78(9) y
O2 C1 O1 124.44(11) n
O2 C1 C11 123.74(11) n
O1 C1 C11 111.81(9) n
O1 C2 C7 107.54(8) n
O1 C2 C3 111.58(9) n
C7 C2 C3 109.97(9) y
C4 C3 C10 110.21(10) n
C4 C3 C2 111.13(9) y
C10 C3 C2 113.09(9) n
C5 C4 C3 125.83(11) y
C4 C5 C6 119.71(11) y
C5 C6 C9 121.68(10) y
C5 C6 C7 110.27(9) y
C9 C6 C7 100.63(9) y
C2 C7 C8 120.39(9) y
C2 C7 C6 107.91(8) y
C8 C7 C6 100.88(9) y
O3 C8 C7 104.63(9) y
O3 C9 C6 104.32(9) y
C12 C11 C16 119.97(11) n
C12 C11 C1 121.73(10) n
C16 C11 C1 118.29(10) n
C13 C12 C11 120.33(11) n
C14 C13 C12 118.14(12) n
C15 C14 C13 122.93(11) n
C15 C14 N1 118.79(11) n
C13 C14 N1 118.28(12) n
C14 C15 C16 118.47(11) n
C15 C16 C11 120.14(12) n
O4 N1 O5 124.01(13) n
O4 N1 C14 117.96(14) n
O5 N1 C14 118.01(12) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.3336(14) n
O1 C2 1.4597(12) n
O2 C1 1.2049(14) n
O3 C9 1.4430(15) y
O3 C8 1.4500(15) y
O4 N1 1.214(2) n
O5 N1 1.221(2) n
C1 C11 1.492(2) n
C2 C7 1.5027(14) y
C2 C3 1.546(2) y
C3 C4 1.515(2) y
C3 C10 1.534(2) n
C4 C5 1.326(2) y
C5 C6 1.497(2) y
C6 C9 1.517(2) y
C6 C7 1.5266(14) y
C7 C8 1.516(2) y
C11 C12 1.389(2) n
C11 C16 1.395(2) n
C12 C13 1.388(2) n
C13 C14 1.379(2) n
C14 C15 1.377(2) n
C14 N1 1.477(2) n
C15 C16 1.383(2) n