#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028908.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4028908
loop_
_publ_author_name
'Fleming, Fraser F.'
'Liu, Wang'
'Ghosh, Somraj'
'Steward, Omar W.'
_publ_section_title
;
 Metalated Nitriles:  Internal 1,2-Asymmetric Induction
;
_journal_issue                   7
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              2803
_journal_page_last               2810
_journal_paper_doi               10.1021/jo702681e
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C17 H20 N2 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35
_chemical_melting_point          349.0(10)
_chemical_name_systematic
; 
 (2R,3R,E)-2-cyano-2,3,4-trimethylhex-4-enyl 4-nitrobenzoate 
;
_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_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                   14.316(11)
_cell_length_b                   7.443(6)
_cell_length_c                   31.78(3)
_cell_measurement_temperature    296(2)
_cell_volume                     3386(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0921
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4850
_diffrn_reflns_theta_full        18.84
_diffrn_reflns_theta_max         18.84
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0436
_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)+(0.1000P)²+0.1474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1517
_reflns_number_gt                1084
_reflns_number_total             1332
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702681esup1.cif
_cod_data_source_block           som010
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '348 - 350 k' was changed to
'349.0(10)' - the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4028908
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
O1 O 0.4474(3) -0.1667(5) 0.80677(10) 0.1097(13) Uani 1 1 d .
O2 O 0.3126(3) -0.1361(5) 0.83354(11) 0.1251(15) Uani 1 1 d .
O3 O 0.29389(18) 0.2212(4) 0.62207(9) 0.0826(10) Uani 1 1 d .
O4 O 0.1496(2) 0.1750(3) 0.64476(6) 0.0600(8) Uani 1 1 d .
N1 N 0.3664(3) -0.1239(5) 0.80458(12) 0.0767(11) Uani 1 1 d .
N2 N -0.0648(2) 0.3071(5) 0.67528(12) 0.0771(11) Uani 1 1 d .
C9 C 0.0115(2) 0.2178(5) 0.60331(9) 0.0508(10) Uani 1 1 d .
C1 C 0.3327(3) -0.0437(5) 0.76480(12) 0.0596(11) Uani 1 1 d .
C5 C 0.2080(3) 0.0378(5) 0.72027(13) 0.0582(11) Uani 1 1 d .
H5 H 0.1443 0.0469 0.7151 0.070 Uiso 1 1 calc R
C8 C 0.1146(3) 0.2584(5) 0.60665(10) 0.0606(11) Uani 1 1 d .
H8A H 0.1474 0.2111 0.5823 0.073 Uiso 1 1 calc R
H8B H 0.1245 0.3873 0.6077 0.073 Uiso 1 1 calc R
C4 C 0.2706(3) 0.0920(4) 0.69012(12) 0.0498(10) Uani 1 1 d .
C3 C 0.3650(3) 0.0790(5) 0.69776(12) 0.0612(11) Uani 1 1 d .
H3 H 0.4076 0.1171 0.6775 0.073 Uiso 1 1 calc R
C6 C 0.2388(3) -0.0301(5) 0.75830(13) 0.0609(11) Uani 1 1 d .
H6 H 0.1966 -0.0657 0.7789 0.073 Uiso 1 1 calc R
C7 C 0.2420(3) 0.1691(5) 0.64903(13) 0.0558(11) Uani 1 1 d .
C15 C -0.1206(3) 0.2678(5) 0.55019(11) 0.0598(11) Uani 1 1 d .
C10 C -0.0327(3) 0.2688(5) 0.64384(13) 0.0573(11) Uani 1 1 d .
C16 C -0.1272(3) 0.2003(5) 0.51158(12) 0.0769(13) Uani 1 1 d .
H16 H -0.0719 0.1946 0.4963 0.092 Uiso 1 1 calc R
C12 C -0.0285(2) 0.3322(5) 0.56640(11) 0.0609(11) Uani 1 1 d .
H12 H 0.0156 0.3178 0.5431 0.073 Uiso 1 1 calc R
C2 C 0.3964(3) 0.0099(5) 0.73522(14) 0.0650(11) Uani 1 1 d .
H2 H 0.4601 -0.0004 0.7404 0.078 Uiso 1 1 calc R
C14 C -0.2028(3) 0.2839(6) 0.57878(12) 0.0804(14) Uani 1 1 d .
H14A H -0.2593 0.2700 0.5628 0.121 Uiso 1 1 calc R
H14B H -0.2024 0.4000 0.5920 0.121 Uiso 1 1 calc R
H14C H -0.1997 0.1922 0.6000 0.121 Uiso 1 1 calc R
C11 C -0.0033(3) 0.0151(4) 0.59640(11) 0.0671(11) Uani 1 1 d .
H11A H 0.0292 -0.0509 0.6179 0.101 Uiso 1 1 calc R
H11B H 0.0206 -0.0183 0.5693 0.101 Uiso 1 1 calc R
H11C H -0.0688 -0.0119 0.5978 0.101 Uiso 1 1 calc R
C17 C -0.2118(3) 0.1328(7) 0.48978(14) 0.1107(17) Uani 1 1 d .
H17A H -0.2101 0.0040 0.4887 0.166 Uiso 1 1 calc R
H17B H -0.2137 0.1800 0.4617 0.166 Uiso 1 1 calc R
H17C H -0.2665 0.1708 0.5048 0.166 Uiso 1 1 calc R
C13 C -0.0300(3) 0.5351(5) 0.57647(14) 0.0911(14) Uani 1 1 d .
H13A H -0.0521 0.6003 0.5524 0.137 Uiso 1 1 calc R
H13B H 0.0320 0.5745 0.5834 0.137 Uiso 1 1 calc R
H13C H -0.0707 0.5568 0.5999 0.137 Uiso 1 1 calc R
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
C7 O4 C8 116.3(3)
O2 N1 O1 123.5(4)
O2 N1 C1 118.4(4)
O1 N1 C1 118.0(4)
C10 C9 C8 107.7(3)
C10 C9 C11 108.4(3)
C8 C9 C11 109.9(3)
C10 C9 C12 110.9(3)
C8 C9 C12 107.6(3)
C11 C9 C12 112.2(3)
C6 C1 C2 122.1(4)
C6 C1 N1 118.7(4)
C2 C1 N1 119.2(4)
C4 C5 C6 120.7(4)
O4 C8 C9 108.1(3)
C5 C4 C3 119.8(3)
C5 C4 C7 123.2(4)
C3 C4 C7 117.0(4)
C2 C3 C4 120.0(4)
C1 C6 C5 118.3(4)
O3 C7 O4 122.2(3)
O3 C7 C4 125.7(4)
O4 C7 C4 112.2(4)
C16 C15 C14 122.5(4)
C16 C15 C12 120.1(3)
C14 C15 C12 117.4(3)
N2 C10 C9 178.6(4)
C15 C16 C17 128.1(4)
C15 C12 C13 111.9(3)
C15 C12 C9 114.1(3)
C13 C12 C9 112.5(3)
C1 C2 C3 119.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.205(4)
O2 N1 1.203(4)
O3 C7 1.199(4)
O4 C7 1.330(4)
O4 C8 1.450(4)
N1 C1 1.479(5)
N2 C10 1.136(4)
C9 C10 1.484(5)
C9 C8 1.510(5)
C9 C11 1.539(5)
C9 C12 1.559(5)
C1 C6 1.364(5)
C1 C2 1.368(5)
C5 C4 1.372(5)
C5 C6 1.382(5)
C4 C3 1.376(5)
C4 C7 1.484(5)
C3 C2 1.372(5)
C15 C16 1.329(5)
C15 C14 1.492(5)
C15 C12 1.495(5)
C16 C17 1.483(5)
C12 C13 1.544(5)
