#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023678.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_4023678
loop_
_publ_author_name
'Sebastian Stecko'
'Adam Mames'
'Bartłomiej Furman'
'Marek Chmielewski'
_publ_section_title
;
 Diastereoselective Synthesis of Carbapenams via Kinugasa Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7402
_journal_page_last               7404
_journal_paper_doi               10.1021/jo801212q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C16 H21 N O2'
_chemical_formula_sum            'C16 H21 N O2'
_chemical_formula_weight         259.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.0842(10)
_cell_length_b                   15.1606(14)
_cell_length_c                   15.7441(18)
_cell_measurement_reflns_used    15
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.34
_cell_measurement_theta_min      18.55
_cell_volume                     1452.2(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0913
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1536
_diffrn_reflns_theta_full        74.10
_diffrn_reflns_theta_max         74.10
_diffrn_reflns_theta_min         5.84
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.8844
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         1536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.0556
_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)+(0.0774P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                900
_reflns_number_total             1536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801212q_si_001.cif
_cod_data_source_block           am_118b
_cod_database_code               4023678
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'
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
O2 O 0.8146(4) 0.50291(17) 0.50617(19) 0.0506(8) Uani 1 1 d . . .
C4 C 1.0191(7) 0.4619(3) 0.4883(3) 0.0465(11) Uani 1 1 d . . .
H4 H 1.1314 0.5066 0.4765 0.056 Uiso 1 1 calc R . .
C7 C 0.8187(7) 0.5894(3) 0.5436(3) 0.0453(11) Uani 1 1 d . . .
C5 C 1.0990(10) 0.3988(3) 0.5580(3) 0.0676(15) Uani 1 1 d . . .
H5A H 1.1794 0.4309 0.6014 0.081 Uiso 1 1 calc R . .
H5B H 0.9753 0.3693 0.5845 0.081 Uiso 1 1 calc R . .
C6 C 1.2483(9) 0.3321(3) 0.5142(3) 0.0770(17) Uani 1 1 d . . .
H6A H 1.4015 0.3492 0.5187 0.092 Uiso 1 1 calc R . .
H6B H 1.2295 0.2736 0.5379 0.092 Uiso 1 1 calc R . .
C16 C 0.9793(9) 0.5651(3) 0.2598(3) 0.0555(13) Uani 1 1 d . . .
H16 H 0.8463 0.5377 0.2476 0.067 Uiso 1 1 calc R . .
C10 C 0.8894(9) 0.6575(3) 0.4793(3) 0.0728(15) Uani 1 1 d . . .
H10A H 0.7973 0.6534 0.4299 0.109 Uiso 1 1 calc R . .
H10B H 1.0395 0.6470 0.4634 0.109 Uiso 1 1 calc R . .
H10C H 0.8764 0.7153 0.5036 0.109 Uiso 1 1 calc R . .
C8 C 0.5745(7) 0.6042(4) 0.5669(3) 0.0624(14) Uani 1 1 d . . .
H8A H 0.4866 0.6016 0.5163 0.094 Uiso 1 1 calc R . .
H8B H 0.5577 0.6610 0.5931 0.094 Uiso 1 1 calc R . .
H8C H 0.5276 0.5591 0.6057 0.094 Uiso 1 1 calc R . .
C9 C 0.9566(8) 0.5946(4) 0.6226(3) 0.0687(15) Uani 1 1 d . . .
H9A H 0.9081 0.5508 0.6625 0.103 Uiso 1 1 calc R . .
H9B H 0.9420 0.6521 0.6475 0.103 Uiso 1 1 calc R . .
H9C H 1.1078 0.5842 0.6084 0.103 Uiso 1 1 calc R . .
H1 H 0.813(9) 0.378(3) 0.414(3) 0.089(17) Uiso 1 1 d . . .
C3 C 0.9947(8) 0.4002(3) 0.4130(3) 0.0478(11) Uani 1 1 d . . .
C12 C 1.3405(8) 0.5607(3) 0.3186(3) 0.0539(12) Uani 1 1 d . . .
H12 H 1.4534 0.5309 0.3462 0.065 Uiso 1 1 calc R . .
N1 N 1.1718(7) 0.3359(2) 0.4256(3) 0.0595(11) Uani 1 1 d . . .
O1 O 1.4788(7) 0.3515(3) 0.3358(3) 0.0833(13) Uani 1 1 d . . .
C13 C 1.3667(9) 0.6466(3) 0.2951(3) 0.0604(13) Uani 1 1 d . . .
H13 H 1.4983 0.6751 0.3074 0.073 Uiso 1 1 calc R . .
C11 C 1.1401(8) 0.5172(3) 0.3004(3) 0.0469(11) Uani 1 1 d . . .
C2 C 1.1032(7) 0.4225(3) 0.3250(3) 0.0494(12) Uani 1 1 d . . .
H2 H 1.0250 0.3917 0.2794 0.059 Uiso 1 1 calc R . .
C1 C 1.2921(10) 0.3652(3) 0.3576(3) 0.0612(15) Uani 1 1 d . . .
C14 C 1.2045(10) 0.6920(3) 0.2541(3) 0.0654(15) Uani 1 1 d . . .
H14 H 1.2272 0.7503 0.2379 0.078 Uiso 1 1 calc R . .
C15 C 1.0069(10) 0.6512(3) 0.2367(3) 0.0618(14) Uani 1 1 d . . .
H15 H 0.8943 0.6818 0.2098 0.074 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C4 O2 C7 117.7(3) . . ?
O2 C4 C3 109.8(4) . . ?
O2 C4 C5 114.1(4) . . ?
C3 C4 C5 101.8(3) . . ?
O2 C7 C9 113.4(4) . . ?
O2 C7 C10 110.7(3) . . ?
C9 C7 C10 111.2(4) . . ?
O2 C7 C8 102.3(4) . . ?
C9 C7 C8 109.5(4) . . ?
C10 C7 C8 109.5(4) . . ?
C6 C5 C4 106.2(4) . . ?
N1 C6 C5 102.4(4) . . ?
C15 C16 C11 122.7(5) . . ?
N1 C3 C4 103.4(4) . . ?
N1 C3 C2 87.3(3) . . ?
C4 C3 C2 121.0(4) . . ?
C13 C12 C11 119.4(5) . . ?
C1 N1 C3 94.1(4) . . ?
C1 N1 C6 125.8(5) . . ?
C3 N1 C6 112.7(4) . . ?
C12 C13 C14 121.7(5) . . ?
C16 C11 C12 117.4(4) . . ?
C16 C11 C2 121.2(4) . . ?
C12 C11 C2 121.4(4) . . ?
C11 C2 C1 121.1(4) . . ?
C11 C2 C3 119.7(3) . . ?
C1 C2 C3 84.1(4) . . ?
O1 C1 N1 132.0(5) . . ?
O1 C1 C2 135.4(5) . . ?
N1 C1 C2 92.6(4) . . ?
C13 C14 C15 119.9(5) . . ?
C16 C15 C14 118.9(5) . . ?
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
O2 C4 1.419(5) . ?
O2 C7 1.439(5) . ?
C4 C3 1.517(6) . ?
C4 C5 1.535(6) . ?
C7 C9 1.502(6) . ?
C7 C10 1.509(6) . ?
C7 C8 1.546(6) . ?
C5 C6 1.524(6) . ?
C6 N1 1.471(6) . ?
C16 C15 1.365(6) . ?
C16 C11 1.376(6) . ?
C3 N1 1.467(6) . ?
C3 C2 1.571(6) . ?
C12 C13 1.364(6) . ?
C12 C11 1.416(6) . ?
N1 C1 1.372(6) . ?
O1 C1 1.204(6) . ?
C13 C14 1.365(7) . ?
C11 C2 1.503(6) . ?
C2 C1 1.529(7) . ?
C14 C15 1.379(8) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658745
