#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024004.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_4024004
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         'C12 H17 N O5'
_chemical_formula_sum            'C12 H17 N O5'
_chemical_formula_weight         255.27
_chemical_melting_point          385.5(5)
_chemical_name_systematic
; 
(1R,2S,3R)-methyl 1-cyano-3-(methoxycarbonyloxy)-
2,3-dimethylcyclopentanecarboxylate  
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'May. 30, 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.3510(15)
_cell_length_b                   12.071(2)
_cell_length_c                   28.875(6)
_cell_measurement_reflns_used    25795
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      2.4
_cell_volume                     2562.2(9)
_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  'SHELXTL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Smart Apex II'
_diffrn_measurement_method       '\fandω 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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25795
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         3.11
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         3265
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9949
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0584P)²+0.5917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1278
_reflns_number_gt                2410
_reflns_number_total             3265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070678ysi20070407_010240_1.cif
_cod_data_source_block           ffgw11_14b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '385-386 K ' was changed to
'385.5(5)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4024004
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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 -0.00058(18) 0.92180(11) 0.39866(5) 0.0355(3) Uani 1 1 d . . .
C2 C 0.21088(19) 0.92139(13) 0.39869(5) 0.0395(3) Uani 1 1 d . . .
H2 H 0.2480 0.8556 0.4162 0.047 Uiso 1 1 calc R . .
C3 C 0.26248(19) 0.89955(12) 0.34844(5) 0.0370(3) Uani 1 1 d . . .
C4 C 0.1226(2) 0.81519(12) 0.33373(5) 0.0428(3) Uani 1 1 d . . .
H4A H 0.1551 0.7421 0.3449 0.051 Uiso 1 1 calc R . .
H4B H 0.1129 0.8126 0.3002 0.051 Uiso 1 1 calc R . .
C5 C -0.05445(19) 0.85337(13) 0.35509(5) 0.0408(3) Uani 1 1 d . . .
H5A H -0.1288 0.7903 0.3638 0.049 Uiso 1 1 calc R . .
H5B H -0.1222 0.8989 0.3334 0.049 Uiso 1 1 calc R . .
C6 C -0.0743(2) 1.03382(14) 0.39535(5) 0.0493(4) Uani 1 1 d . . .
C7 C -0.0831(2) 0.87035(13) 0.44179(5) 0.0420(3) Uani 1 1 d . . .
C8 C -0.0879(3) 0.71225(17) 0.48891(7) 0.0648(5) Uani 1 1 d . . .
H8A H -0.1059 0.7601 0.5151 0.097 Uiso 1 1 calc R . .
H8B H -0.0074 0.6530 0.4974 0.097 Uiso 1 1 calc R . .
H8C H -0.2028 0.6822 0.4793 0.097 Uiso 1 1 calc R . .
C9 C 0.3012(3) 1.01867(18) 0.42184(6) 0.0675(5) Uani 1 1 d . . .
H9A H 0.4306 1.0081 0.4218 0.101 Uiso 1 1 calc R . .
H9B H 0.2586 1.0247 0.4532 0.101 Uiso 1 1 calc R . .
H9C H 0.2720 1.0853 0.4053 0.101 Uiso 1 1 calc R . .
C10 C 0.24815(19) 1.01307(12) 0.27981(5) 0.0366(3) Uani 1 1 d . . .
C11 C 0.2283(3) 1.14422(16) 0.22083(6) 0.0584(5) Uani 1 1 d . . .
H11A H 0.3483 1.1241 0.2108 0.088 Uiso 1 1 calc R . .
H11B H 0.2113 1.2225 0.2169 0.088 Uiso 1 1 calc R . .
H11C H 0.1398 1.1050 0.2027 0.088 Uiso 1 1 calc R . .
C12 C 0.4588(2) 0.86724(17) 0.34231(7) 0.0621(5) Uani 1 1 d . . .
H12A H 0.4807 0.8489 0.3104 0.093 Uiso 1 1 calc R . .
H12B H 0.4853 0.8042 0.3614 0.093 Uiso 1 1 calc R . .
H12C H 0.5354 0.9280 0.3512 0.093 Uiso 1 1 calc R . .
N1 N -0.1333(3) 1.11961(14) 0.39264(7) 0.0810(6) Uani 1 1 d . . .
O1 O -0.2050(2) 0.91002(12) 0.46287(5) 0.0848(5) Uani 1 1 d . . .
O2 O -0.00933(16) 0.77448(10) 0.45136(4) 0.0531(3) Uani 1 1 d . . .
O3 O 0.22575(13) 1.00497(8) 0.32532(3) 0.0365(2) Uani 1 1 d . . .
O4 O 0.29636(18) 0.94339(10) 0.25369(4) 0.0569(3) Uani 1 1 d . . .
O5 O 0.20640(15) 1.11599(8) 0.26870(3) 0.0462(3) 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 C7 106.52(12) . . ?
C6 C1 C2 111.97(13) . . ?
C7 C1 C2 113.43(12) . . ?
C6 C1 C5 110.14(12) . . ?
C7 C1 C5 110.15(12) . . ?
C2 C1 C5 104.67(11) . . ?
C9 C2 C3 116.63(13) . . ?
C9 C2 C1 116.03(14) . . ?
C3 C2 C1 104.42(11) . . ?
C9 C2 H2 106.3 . . ?
C3 C2 H2 106.3 . . ?
C1 C2 H2 106.3 . . ?
O3 C3 C12 110.42(12) . . ?
O3 C3 C4 109.47(11) . . ?
C12 C3 C4 116.45(14) . . ?
O3 C3 C2 103.79(11) . . ?
C12 C3 C2 113.30(13) . . ?
C4 C3 C2 102.45(11) . . ?
C3 C4 C5 105.43(11) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C4 C5 C1 105.81(11) . . ?
C4 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
N1 C6 C1 179.1(2) . . ?
O1 C7 O2 124.26(14) . . ?
O1 C7 C1 123.95(14) . . ?
O2 C7 C1 111.70(12) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 O5 125.71(13) . . ?
O4 C10 O3 127.96(13) . . ?
O5 C10 O3 106.33(11) . . ?
O5 C11 H11A 109.5 . . ?
O5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12A 109.5 . . ?
C3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 O2 C8 117.03(13) . . ?
C10 O3 C3 119.54(10) . . ?
C10 O5 C11 115.62(13) . . ?
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 1.460(2) . ?
C1 C7 1.5181(19) . ?
C1 C2 1.554(2) . ?
C1 C5 1.556(2) . ?
C2 C9 1.505(2) . ?
C2 C3 1.5229(19) . ?
C2 H2 0.9800 . ?
C3 O3 1.4621(16) . ?
C3 C12 1.505(2) . ?
C3 C4 1.508(2) . ?
C4 C5 1.513(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.125(2) . ?
C7 O1 1.1846(18) . ?
C7 O2 1.3074(18) . ?
C8 O2 1.4400(19) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O4 1.1841(17) . ?
C10 O5 1.3193(17) . ?
C10 O3 1.3280(16) . ?
C11 O5 1.4325(18) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
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 C9 33.63(18) . . . . ?
C7 C1 C2 C9 -86.97(16) . . . . ?
C5 C1 C2 C9 152.93(13) . . . . ?
C6 C1 C2 C3 -96.21(14) . . . . ?
C7 C1 C2 C3 143.19(12) . . . . ?
C5 C1 C2 C3 23.09(14) . . . . ?
C9 C2 C3 O3 -54.70(17) . . . . ?
C1 C2 C3 O3 74.77(13) . . . . ?
C9 C2 C3 C12 65.09(19) . . . . ?
C1 C2 C3 C12 -165.43(13) . . . . ?
C9 C2 C3 C4 -168.64(15) . . . . ?
C1 C2 C3 C4 -39.16(14) . . . . ?
O3 C3 C4 C5 -68.94(14) . . . . ?
C12 C3 C4 C5 164.96(13) . . . . ?
C2 C3 C4 C5 40.75(14) . . . . ?
C3 C4 C5 C1 -26.22(15) . . . . ?
C6 C1 C5 C4 122.18(13) . . . . ?
C7 C1 C5 C4 -120.61(13) . . . . ?
C2 C1 C5 C4 1.66(15) . . . . ?
C7 C1 C6 N1 -71(11) . . . . ?
C2 C1 C6 N1 164(100) . . . . ?
C5 C1 C6 N1 48(11) . . . . ?
C6 C1 C7 O1 11.1(2) . . . . ?
C2 C1 C7 O1 134.73(18) . . . . ?
C5 C1 C7 O1 -108.33(19) . . . . ?
C6 C1 C7 O2 -172.16(13) . . . . ?
C2 C1 C7 O2 -48.53(17) . . . . ?
C5 C1 C7 O2 68.41(16) . . . . ?
O1 C7 O2 C8 2.6(3) . . . . ?
C1 C7 O2 C8 -174.17(15) . . . . ?
O4 C10 O3 C3 0.0(2) . . . . ?
O5 C10 O3 C3 -179.77(11) . . . . ?
C12 C3 O3 C10 61.59(17) . . . . ?
C4 C3 O3 C10 -67.88(15) . . . . ?
C2 C3 O3 C10 -176.68(11) . . . . ?
O4 C10 O5 C11 -2.1(2) . . . . ?
O3 C10 O5 C11 177.66(12) . . . . ?
