#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024007.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024007
loop_
_publ_author_name
'Fraser F. Fleming'
'Guoqing Wei'
'Zhiyu Zhang'
'Omar W. Steward'
_publ_contact_author_address
;
 Department of Chemistry and Biochemistry
 Duquesne University
 Pittsburgh, PA 15282 USA
;
_publ_contact_author_email       steward@duq.edu
_publ_contact_author_fax         '412 396 5683'
_publ_contact_author_name        'Dr.Omar W. Steward'
_publ_contact_author_phone       '412 396 6338'
_publ_section_title
;
 Cyclic Oxonitriles: Stereodivergent Grignard Addition-Alkylations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5270
_journal_page_last               5275
_journal_paper_doi               10.1021/jo070678y
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C20 H24 N2 O5'
_chemical_formula_sum            'C20 H24 N2 O5'
_chemical_formula_weight         372.41
_chemical_name_systematic
; 
(1R,2S,3S)3-cyano-1,2-dimethyl-3-pivaloylcyclopentyl 
4-nitrobenzoate 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'May. 22, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.738(5)
_cell_angle_beta                 97.890(5)
_cell_angle_gamma                90.954(5)
_cell_formula_units_Z            2
_cell_length_a                   7.028(3)
_cell_length_b                   10.388(4)
_cell_length_c                   13.769(5)
_cell_measurement_reflns_used    8275
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.4
_cell_volume                     966.0(6)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Samrt Apex II'
_diffrn_measurement_method       'φ and ω 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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8275
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         26.22
_diffrn_reflns_theta_min         1.54
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3803
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABSsheldrick, 2002'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1142P)²+0.2313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1857
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                2471
_reflns_number_total             3803
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo070678ysi20070407_010240_4.cif
_cod_data_source_block           ffgw001_14k
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4024007
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.3336(3) 0.2250(2) 0.89366(19) 0.0432(6) Uani 1 1 d . . .
C2 C 0.3127(4) 0.1335(2) 0.78619(19) 0.0454(6) Uani 1 1 d . . .
H9 H 0.3637 0.0487 0.7939 0.055 Uiso 1 1 calc R . .
C3 C 0.4546(4) 0.1946(2) 0.7333(2) 0.0497(6) Uani 1 1 d . . .
C4 C 0.6239(4) 0.2455(3) 0.8163(2) 0.0609(7) Uani 1 1 d . . .
H4A H 0.7217 0.1805 0.8133 0.073 Uiso 1 1 calc R . .
H4B H 0.6805 0.3272 0.8077 0.073 Uiso 1 1 calc R . .
C5 C 0.5499(4) 0.2698(4) 0.9162(2) 0.0693(9) Uani 1 1 d . . .
H5A H 0.5663 0.3632 0.9503 0.083 Uiso 1 1 calc R . .
H5B H 0.6195 0.2194 0.9591 0.083 Uiso 1 1 calc R . .
C6 C 0.2149(5) 0.3392(3) 0.8938(2) 0.0602(8) Uani 1 1 d . . .
C7 C 0.2856(4) 0.1492(2) 0.9725(2) 0.0475(6) Uani 1 1 d . . .
C8 C 0.2429(4) 0.2201(3) 1.0771(2) 0.0540(7) Uani 1 1 d . . .
C9 C 0.0266(5) 0.2409(3) 1.0665(3) 0.0756(9) Uani 1 1 d . . .
H9A H -0.0046 0.2991 1.0226 0.113 Uiso 1 1 calc R . .
H9B H -0.0083 0.2796 1.1317 0.113 Uiso 1 1 calc R . .
H9C H -0.0430 0.1570 1.0385 0.113 Uiso 1 1 calc R . .
C10 C 0.2879(8) 0.1292(4) 1.1478(3) 0.1036(15) Uani 1 1 d . . .
H10A H 0.2194 0.0450 1.1194 0.155 Uiso 1 1 calc R . .
H10B H 0.2494 0.1685 1.2121 0.155 Uiso 1 1 calc R . .
H10C H 0.4236 0.1166 1.1566 0.155 Uiso 1 1 calc R . .
C11 C 0.3506(6) 0.3543(4) 1.1200(2) 0.0837(11) Uani 1 1 d . . .
H11A H 0.4865 0.3431 1.1241 0.126 Uiso 1 1 calc R . .
H11B H 0.3195 0.3921 1.1863 0.126 Uiso 1 1 calc R . .
H11C H 0.3135 0.4124 1.0767 0.126 Uiso 1 1 calc R . .
C12 C 0.1092(4) 0.1018(3) 0.7317(2) 0.0620(8) Uani 1 1 d . . .
H12A H 0.0480 0.1829 0.7283 0.093 Uiso 1 1 calc R . .
H12B H 0.0386 0.0536 0.7678 0.093 Uiso 1 1 calc R . .
H12C H 0.1120 0.0490 0.6646 0.093 Uiso 1 1 calc R . .
C13 C 0.5031(5) 0.1005(3) 0.6379(2) 0.0729(9) Uani 1 1 d . . .
H13A H 0.3925 0.0852 0.5865 0.109 Uiso 1 1 calc R . .
H13B H 0.5396 0.0177 0.6526 0.109 Uiso 1 1 calc R . .
H13C H 0.6076 0.1392 0.6146 0.109 Uiso 1 1 calc R . .
C14 C 0.4347(4) 0.3927(3) 0.66437(19) 0.0478(6) Uani 1 1 d . . .
C15 C 0.2973(4) 0.4931(2) 0.64152(18) 0.0451(6) Uani 1 1 d . . .
C16 C 0.1080(4) 0.4893(3) 0.65799(19) 0.0490(6) Uani 1 1 d . . .
H16 H 0.0632 0.4240 0.6864 0.059 Uiso 1 1 calc R . .
C17 C -0.0150(4) 0.5820(3) 0.63251(19) 0.0497(6) Uani 1 1 d . . .
H17 H -0.1425 0.5802 0.6437 0.060 Uiso 1 1 calc R . .
C18 C 0.0547(4) 0.6769(2) 0.59039(18) 0.0472(6) Uani 1 1 d . . .
C19 C 0.2419(4) 0.6840(3) 0.5738(2) 0.0571(7) Uani 1 1 d . . .
H19 H 0.2856 0.7497 0.5454 0.069 Uiso 1 1 calc R . .
C20 C 0.3640(4) 0.5915(3) 0.6002(2) 0.0560(7) Uani 1 1 d . . .
H20 H 0.4919 0.5950 0.5901 0.067 Uiso 1 1 calc R . .
N1 N 0.1230(6) 0.4275(3) 0.8920(2) 0.1090(14) Uani 1 1 d . . .
N2 N -0.0788(4) 0.7720(2) 0.55860(17) 0.0581(6) Uani 1 1 d . . .
O1 O 0.3517(2) 0.30613(16) 0.70543(13) 0.0489(5) Uani 1 1 d . . .
O2 O 0.5983(3) 0.3914(2) 0.64772(16) 0.0627(6) Uani 1 1 d . . .
O3 O -0.2427(4) 0.7688(2) 0.5777(2) 0.0878(8) Uani 1 1 d . . .
O4 O -0.0202(4) 0.8471(2) 0.51264(19) 0.0825(7) Uani 1 1 d . . .
O5 O 0.2845(4) 0.02972(18) 0.94837(17) 0.0723(6) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 110.0(2) . . ?
C6 C1 C5 110.4(2) . . ?
C2 C1 C5 103.3(2) . . ?
C6 C1 C7 111.6(2) . . ?
C2 C1 C7 111.91(19) . . ?
C5 C1 C7 109.3(2) . . ?
C12 C2 C3 117.1(2) . . ?
C12 C2 C1 115.9(2) . . ?
C3 C2 C1 104.6(2) . . ?
C12 C2 H9 106.1 . . ?
C3 C2 H9 106.1 . . ?
C1 C2 H9 106.1 . . ?
O1 C3 C4 110.7(2) . . ?
O1 C3 C13 109.1(2) . . ?
C4 C3 C13 115.7(2) . . ?
O1 C3 C2 103.38(18) . . ?
C4 C3 C2 103.7(2) . . ?
C13 C3 C2 113.6(2) . . ?
C5 C4 C3 107.8(2) . . ?
C5 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.5 . . ?
C4 C5 C1 107.1(2) . . ?
C4 C5 H5A 110.3 . . ?
C1 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
C1 C5 H5B 110.3 . . ?
H5A C5 H5B 108.6 . . ?
N1 C6 C1 178.7(3) . . ?
O5 C7 C8 120.2(2) . . ?
O5 C7 C1 117.2(2) . . ?
C8 C7 C1 122.6(2) . . ?
C10 C8 C11 110.6(3) . . ?
C10 C8 C7 108.5(2) . . ?
C11 C8 C7 113.9(2) . . ?
C10 C8 C9 108.2(3) . . ?
C11 C8 C9 108.7(3) . . ?
C7 C8 C9 106.7(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 O1 125.2(2) . . ?
O2 C14 C15 123.8(2) . . ?
O1 C14 C15 111.0(2) . . ?
C16 C15 C20 119.7(2) . . ?
C16 C15 C14 122.5(2) . . ?
C20 C15 C14 117.8(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 118.6(2) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 122.6(2) . . ?
C19 C18 N2 118.7(2) . . ?
C17 C18 N2 118.6(2) . . ?
C18 C19 C20 118.4(2) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 120.5(2) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
O4 N2 O3 123.7(3) . . ?
O4 N2 C18 118.0(3) . . ?
O3 N2 C18 118.3(2) . . ?
C14 O1 C3 122.14(18) . . ?
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 C6 1.462(3) . ?
C1 C2 1.543(4) . ?
C1 C5 1.549(4) . ?
C1 C7 1.553(3) . ?
C2 C12 1.513(4) . ?
C2 C3 1.525(4) . ?
C2 H9 0.9800 . ?
C3 O1 1.475(3) . ?
C3 C4 1.523(4) . ?
C3 C13 1.523(4) . ?
C4 C5 1.504(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.134(4) . ?
C7 O5 1.206(3) . ?
C7 C8 1.526(4) . ?
C8 C10 1.516(4) . ?
C8 C11 1.522(5) . ?
C8 C9 1.531(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.203(3) . ?
C14 O1 1.335(3) . ?
C14 C15 1.492(4) . ?
C15 C16 1.382(3) . ?
C15 C20 1.386(4) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(4) . ?
C18 N2 1.473(3) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N2 O4 1.214(3) . ?
N2 O3 1.218(3) . ?
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
C6 C1 C2 C12 -46.8(3) . . . . ?
C5 C1 C2 C12 -164.7(2) . . . . ?
C7 C1 C2 C12 77.9(3) . . . . ?
C6 C1 C2 C3 83.7(2) . . . . ?
C5 C1 C2 C3 -34.2(2) . . . . ?
C7 C1 C2 C3 -151.65(19) . . . . ?
C12 C2 C3 O1 50.6(3) . . . . ?
C1 C2 C3 O1 -79.2(2) . . . . ?
C12 C2 C3 C4 166.1(2) . . . . ?
C1 C2 C3 C4 36.4(2) . . . . ?
C12 C2 C3 C13 -67.5(3) . . . . ?
C1 C2 C3 C13 162.7(2) . . . . ?
O1 C3 C4 C5 85.7(3) . . . . ?
C13 C3 C4 C5 -149.6(3) . . . . ?
C2 C3 C4 C5 -24.6(3) . . . . ?
C3 C4 C5 C1 3.3(3) . . . . ?
C6 C1 C5 C4 -98.6(3) . . . . ?
C2 C1 C5 C4 19.0(3) . . . . ?
C7 C1 C5 C4 138.3(2) . . . . ?
C2 C1 C6 N1 -23(17) . . . . ?
C5 C1 C6 N1 90(17) . . . . ?
C7 C1 C6 N1 -148(17) . . . . ?
C6 C1 C7 O5 140.9(3) . . . . ?
C2 C1 C7 O5 17.2(3) . . . . ?
C5 C1 C7 O5 -96.6(3) . . . . ?
C6 C1 C7 C8 -39.7(3) . . . . ?
C2 C1 C7 C8 -163.4(2) . . . . ?
C5 C1 C7 C8 82.8(3) . . . . ?
O5 C7 C8 C10 23.8(4) . . . . ?
C1 C7 C8 C10 -155.6(3) . . . . ?
O5 C7 C8 C11 147.5(3) . . . . ?
C1 C7 C8 C11 -31.9(4) . . . . ?
O5 C7 C8 C9 -92.6(3) . . . . ?
C1 C7 C8 C9 88.0(3) . . . . ?
O2 C14 C15 C16 177.5(3) . . . . ?
O1 C14 C15 C16 -2.6(3) . . . . ?
O2 C14 C15 C20 -1.0(4) . . . . ?
O1 C14 C15 C20 178.8(2) . . . . ?
C20 C15 C16 C17 0.7(4) . . . . ?
C14 C15 C16 C17 -177.9(2) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C16 C17 C18 N2 177.1(2) . . . . ?
C17 C18 C19 C20 0.4(4) . . . . ?
N2 C18 C19 C20 -177.5(2) . . . . ?
C18 C19 C20 C15 0.6(4) . . . . ?
C16 C15 C20 C19 -1.1(4) . . . . ?
C14 C15 C20 C19 177.5(2) . . . . ?
C19 C18 N2 O4 4.9(4) . . . . ?
C17 C18 N2 O4 -173.0(2) . . . . ?
C19 C18 N2 O3 -176.8(3) . . . . ?
C17 C18 N2 O3 5.3(4) . . . . ?
O2 C14 O1 C3 -1.5(4) . . . . ?
C15 C14 O1 C3 178.6(2) . . . . ?
C4 C3 O1 C14 63.8(3) . . . . ?
C13 C3 O1 C14 -64.5(3) . . . . ?
C2 C3 O1 C14 174.3(2) . . . . ?
