#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:12:02 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178940 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/69/4116933.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_4116933
loop_
_publ_author_name
'Gary A. Molander'
'J. Christopher McWilliams'
'Bruce C. Noll'
_publ_section_title
;
 Remote Stereochemical Control of Both Reacting Centers in Ketyl-Olefin
 Radical Cyclizations: Involvement of a Samarium Tridentate Ligate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1265
_journal_page_last               1276
_journal_paper_doi               10.1021/ja963195c
_journal_volume                  119
_journal_year                    1997
_chemical_formula_sum            'C16 H28 N2 O5'
_chemical_formula_weight         328.40
_chemical_name_systematic
; 
(2R,3R)-O-((E)-2-((1R,2R)-2-Hydroxy-2-methylcyclopentyl)vinyl)-
N,N,N',N'-tetramethylsuccinamide
;
_space_group_IT_number           1
_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_method           SHELXL
_cell_angle_alpha                101.89(3)
_cell_angle_beta                 93.06(3)
_cell_angle_gamma                94.15(3)
_cell_formula_units_Z            1
_cell_length_a                   6.0950(10)
_cell_length_b                   7.659(2)
_cell_length_c                   10.042(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      10
_cell_volume                     456.39(18)
_computing_cell_refinement       'SIEMENS P3'
_computing_data_collection       'SIEMENS P3'
_computing_data_reduction        'SIEMENS XTAPE'
_computing_molecular_graphics    'SHELXTL v.4 (Siemens, Sheldrick, 1990)'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL v.4 (Siemens, Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nicotet P3'
_diffrn_measurement_method       'adaptive ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            1801
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 198
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             178
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.92(170)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.020
_refine_ls_goodness_of_fit_obs   1.082
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.019
_refine_ls_restrained_S_obs      1.081
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_obs          0.0390
_refine_ls_shift/esd_max         -0.169
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0414P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0818
_refine_ls_wR_factor_obs         0.0759
_reflns_number_observed          1324
_reflns_number_total             1667
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja963195c.cif
_cod_data_source_block           27a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        456.4(2)
_cod_database_code               4116933
loop_
_symmetry_equiv_pos_as_xyz
'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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.4301(6) 1.2105(5) 0.5686(4) 0.0579(11) Uani 1 d .
N2 N 0.6477(6) 0.5371(5) 0.3042(3) 0.0475(9) Uani 1 d .
O1 O 0.3143(6) 0.9547(6) 1.0781(3) 0.0925(13) Uani 1 d .
H1 H 0.2924(23) 0.9897(69) 1.1588(5) 0.111 Uiso 1 calc R
O2 O 0.5161(4) 0.8483(3) 0.5949(2) 0.0481(8) Uani 1 d .
O3 O 0.8249(5) 1.0081(4) 0.4367(3) 0.0692(10) Uani 1 d .
H3 H 0.9438(19) 0.9864(31) 0.4053(39) 0.083 Uiso 1 calc R
O4 O 0.2650(5) 1.0831(4) 0.3638(3) 0.0583(9) Uani 1 d .
O5 O 0.9470(5) 0.6843(4) 0.4251(3) 0.0707(10) Uani 1 d .
C1 C 0.1142(7) 0.9520(7) 0.9960(4) 0.0636(14) Uani 1 d .
C2 C 0.1321(7) 0.8102(5) 0.8663(4) 0.0524(13) Uani 1 d .
H2 H 0.0071(7) 0.8177(5) 0.8027(4) 0.063 Uiso 1 calc R
C3 C 0.0931(11) 0.6344(7) 0.9142(5) 0.091(2) Uani 1 d .
H3A H 0.0325(11) 0.5391(7) 0.8392(5) 0.110 Uiso 1 calc R
H3B H 0.2299(11) 0.6001(7) 0.9511(5) 0.110 Uiso 1 calc R
C4 C -0.0703(11) 0.6711(9) 1.0241(6) 0.108(2) Uani 1 d .
H4A H -0.0225(11) 0.6260(9) 1.1034(6) 0.129 Uiso 1 calc R
H4B H -0.2154(11) 0.6140(9) 0.9899(6) 0.129 Uiso 1 calc R
C5 C -0.0755(8) 0.8747(8) 1.0608(4) 0.085(2) Uani 1 d .
H5A H -0.2138(8) 0.9095(8) 1.0263(4) 0.102 Uiso 1 calc R
H5B H -0.0602(8) 0.9172(8) 1.1590(4) 0.102 Uiso 1 calc R
C6 C 0.0870(10) 1.1334(8) 0.9710(6) 0.103(2) Uani 1 d .
H6A H -0.0452(31) 1.1304(13) 0.9139(30) 0.123 Uiso 1 calc R
H6B H 0.2116(28) 1.1720(21) 0.9265(33) 0.123 Uiso 1 calc R
H6C H 0.0771(61) 1.2153(12) 1.0563(7) 0.123 Uiso 1 calc R
C7 C 0.3359(7) 0.8287(5) 0.7946(4) 0.0491(12) Uani 1 d .
H7 H 0.4721(7) 0.8355(5) 0.8427(4) 0.059 Uiso 1 calc R
C8 C 0.3295(7) 0.8356(5) 0.6670(4) 0.0469(11) Uani 1 d .
H8 H 0.1922(7) 0.8318(5) 0.6209(4) 0.056 Uiso 1 calc R
C9 C 0.4665(6) 0.8891(5) 0.4652(4) 0.0407(11) Uani 1 d .
H9 H 0.3494(6) 0.7998(5) 0.4183(4) 0.049 Uiso 1 calc R
C10 C 0.6653(6) 0.8666(5) 0.3801(4) 0.0434(11) Uani 1 d .
H10 H 0.6203(6) 0.8779(5) 0.2873(4) 0.052 Uiso 1 calc R
C11 C 0.3845(7) 1.0729(5) 0.4655(4) 0.0431(11) Uani 1 d .
C12 C 0.3247(10) 1.3764(6) 0.5663(5) 0.097(2) Uani 1 d .
H12A H 0.2929(52) 1.4314(24) 0.6573(7) 0.117 Uiso 1 calc R
H12B H 0.1901(29) 1.3492(8) 0.5092(27) 0.117 Uiso 1 calc R
H12C H 0.4223(23) 1.4572(18) 0.5310(32) 0.117 Uiso 1 calc R
C13 C 0.6020(9) 1.2262(7) 0.6784(4) 0.084(2) Uani 1 d .
H13A H 0.6912(30) 1.3371(19) 0.6872(19) 0.101 Uiso 1 calc R
H13B H 0.6927(30) 1.1281(22) 0.6578(15) 0.101 Uiso 1 calc R
H13C H 0.5351(9) 1.2238(39) 0.7625(7) 0.101 Uiso 1 calc R
C14 C 0.7633(8) 0.6875(6) 0.3716(4) 0.0457(11) Uani 1 d .
C15 C 0.4438(8) 0.5300(6) 0.2217(5) 0.077(2) Uani 1 d .
H15A H 0.4522(18) 0.4498(28) 0.1354(11) 0.092 Uiso 1 calc R
H15B H 0.4208(24) 0.6476(9) 0.2072(23) 0.092 Uiso 1 calc R
H15C H 0.3233(10) 0.4880(35) 0.2679(13) 0.092 Uiso 1 calc R
C16 C 0.7436(9) 0.3683(6) 0.2997(5) 0.083(2) Uani 1 d .
H16A H 0.6427(21) 0.2721(7) 0.2498(25) 0.099 Uiso 1 calc R
H16B H 0.7724(43) 0.3515(18) 0.3909(5) 0.099 Uiso 1 calc R
H16C H 0.8791(25) 0.3697(15) 0.2553(26) 0.099 Uiso 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
C11 N1 C13 126.2(4)
C11 N1 C12 118.7(4)
C13 N1 C12 114.4(4)
C14 N2 C15 125.0(4)
C14 N2 C16 118.3(4)
C15 N2 C16 116.3(4)
C8 O2 C9 112.2(3)
O1 C1 C6 109.7(5)
O1 C1 C5 109.7(4)
C6 C1 C5 114.2(5)
O1 C1 C2 105.9(4)
C6 C1 C2 113.9(4)
C5 C1 C2 103.0(4)
C7 C2 C3 115.2(4)
C7 C2 C1 115.7(4)
C3 C2 C1 103.1(3)
C4 C3 C2 105.3(5)
C3 C4 C5 105.8(4)
C1 C5 C4 106.6(4)
C8 C7 C2 121.7(4)
C7 C8 O2 123.7(4)
O2 C9 C10 110.0(3)
O2 C9 C11 116.6(3)
C10 C9 C11 109.0(3)
O3 C10 C9 107.4(3)
O3 C10 C14 110.2(4)
C9 C10 C14 114.2(3)
O4 C11 N1 121.8(4)
O4 C11 C9 115.6(4)
N1 C11 C9 122.6(4)
O5 C14 N2 121.3(4)
O5 C14 C10 119.3(4)
N2 C14 C10 119.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.318(5)
N1 C13 1.460(5)
N1 C12 1.468(6)
N2 C14 1.339(5)
N2 C15 1.447(5)
N2 C16 1.450(5)
O1 C1 1.432(6)
O2 C8 1.389(4)
O2 C9 1.422(4)
O3 C10 1.407(4)
O4 C11 1.241(5)
O5 C14 1.220(5)
C1 C6 1.481(6)
C1 C5 1.500(6)
C1 C2 1.529(6)
C2 C7 1.481(6)
C2 C3 1.527(6)
C3 C4 1.523(7)
C4 C5 1.530(8)
C7 C8 1.291(5)
C9 C10 1.520(5)
C9 C11 1.527(6)
C10 C14 1.523(6)
