#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007456.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2007456
loop_
_publ_author_name
'Merino, P.'
'Merchan, F. L.'
'Tejero, T.'
'Franco, S.'
_publ_section_title
;
Structures of Chiral Hydroxylamines. VI.
(3R,4S)-N-Benzyl-4,5-dihydroxy-3-(hydroxyamino)-4,5-O-isopropylidene-1-pentyne
;
_journal_issue 7
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 1003
_journal_page_last 1004
_journal_volume 54
_journal_year 1998
_chemical_formula_moiety 'C15 H19 N O3'
_chemical_formula_sum 'C15 H19 N O3'
_chemical_formula_weight 261.31
_chemical_melting_point 388
_chemical_name_systematic
;
(3R,4S)-N-Benzyl-4,5-dihydroxy-3-(hydroxyamino)-4,5-O-isopropylidene-1-pentyne
;
_space_group_IT_number 145
_symmetry_cell_setting trigonal
_symmetry_space_group_name_Hall 'P 32'
_symmetry_space_group_name_H-M 'P 32'
_audit_creation_method SHELXL
_cell_angle_alpha 90.000(5)
_cell_angle_beta 90.000(5)
_cell_angle_gamma 120.000(5)
_cell_formula_units_Z 3
_cell_length_a 13.240(5)
_cell_length_b 13.240(5)
_cell_length_c 7.157(5)
_cell_measurement_reflns_used 39
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 24.92
_cell_measurement_theta_min 9.19
_cell_volume 1086.5(10)
_computing_cell_refinement XSCANS
_computing_data_collection 'XSCANS (Siemens, 1992)'
_computing_data_reduction XSCANS
_computing_molecular_graphics 'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material SHELXTL-Plus
_computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution 'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature 173(2)
_diffrn_measurement_device_type 'Siemens P4'
_diffrn_measurement_method 2\q/\w
_diffrn_radiation_monochromator graphite
_diffrn_radiation_source 'normal-focus sealed tube'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71069
_diffrn_reflns_av_R_equivalents 0.049
_diffrn_reflns_av_sigmaI/netI 0.040
_diffrn_reflns_limit_h_max 15
_diffrn_reflns_limit_h_min -1
_diffrn_reflns_limit_k_max 1
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_l_max 8
_diffrn_reflns_limit_l_min -1
_diffrn_reflns_number 1948
_diffrn_reflns_theta_max 25.49
_diffrn_reflns_theta_min 1.78
_diffrn_standards_decay_% 6.64
_diffrn_standards_interval_count 97
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.083
_exptl_absorpt_correction_type none
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.198
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 420
_exptl_crystal_size_max 0.60
_exptl_crystal_size_mid 0.42
_exptl_crystal_size_min 0.26
_refine_diff_density_max 0.154
_refine_diff_density_min -0.145
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_all 1.062
_refine_ls_goodness_of_fit_ref 1.093
_refine_ls_hydrogen_treatment 'H atoms calculated'
_refine_ls_matrix_type full
_refine_ls_number_parameters 178
_refine_ls_number_reflns 1553
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.076
_refine_ls_restrained_S_obs 1.092
_refine_ls_R_factor_all 0.050
_refine_ls_R_factor_gt 0.041
_refine_ls_shift/su_max 0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0643P)^2^+0.0988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all 0.108
_refine_ls_wR_factor_ref 0.102
_reflns_number_gt 1402
_reflns_number_total 1604
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file na1331.cif
_[local]_cod_data_source_block na1331
_cod_depositor_comments
;
The following automatic conversions were performed:
'_chemical_melting_point' value '388 K' was changed to '388' - the
value should be numeric and without a unit designator.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_database_code 2007456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.0680(2) 0.0666(2) 0.1371(3) 0.0362(5) Uani d . 1 O
H(O) 0.0218(2) 0.045(3) 0.0460(3) 0.051(11) Uiso calc R 1 H
O2 0.2272(2) 0.3407(2) -0.0810(3) 0.0381(5) Uani d . 1 O
O3 0.2976(2) 0.5191(2) 0.0527(3) 0.0429(6) Uani d . 1 O
N1 0.1875(2) 0.1244(2) 0.0690(4) 0.0306(6) Uani d . 1 N
C2 0.2388(3) 0.2203(3) 0.3806(4) 0.0325(7) Uani d . 1 C
C3 0.2501(2) 0.2341(2) 0.1746(4) 0.0293(6) Uani d . 1 C
H3 0.3348(2) 0.2696(2) 0.1439(4) 0.042(4) Uiso calc R 1 H
C4 0.2125(3) 0.3214(3) 0.1150(4) 0.0310(7) Uani d . 1 C
H4 0.1291(3) 0.2912(3) 0.1496(4) 0.042(4) Uiso calc R 1 H
C6 0.2959(3) 0.4637(2) -0.1172(5) 0.0332(7) Uani d . 1 C
C10 0.3528(3) 0.0896(3) 0.0384(5) 0.0395(8) Uani d . 1 C
C9 0.2309(3) 0.0440(3) 0.1126(5) 0.0366(7) Uani d . 1 C
H9A 0.1781(3) -0.0332(3) 0.0567(5) 0.042(4) Uiso calc R 1 H
H9B 0.2308(3) 0.0340(3) 0.2497(5) 0.042(4) Uiso calc R 1 H
C1 0.2270(3) 0.2122(3) 0.5429(5) 0.0442(8) Uani d . 1 C
H1 0.2174(3) 0.2056(3) 0.6747(5) 0.072(13) Uiso calc R 1 H
C5 0.2887(3) 0.4426(3) 0.1985(5) 0.0437(8) Uani d . 1 C
H5A 0.2516(3) 0.4538(3) 0.3105(5) 0.042(4) Uiso calc R 1 H
H5B 0.3665(3) 0.4550(3) 0.2332(5) 0.042(4) Uiso calc R 1 H
C7 0.2354(3) 0.4965(3) -0.2634(5) 0.0423(8) Uani d . 1 C
H7A 0.2337(3) 0.4586(3) -0.3820(5) 0.059(5) Uiso calc R 1 H
H7B 0.2778(3) 0.5813(3) -0.2803(5) 0.059(5) Uiso calc R 1 H
H7C 0.1555(3) 0.4708(3) -0.2230(5) 0.059(5) Uiso calc R 1 H
C8 0.4167(3) 0.4914(3) -0.1763(7) 0.0589(11) Uani d . 1 C
H8A 0.4119(3) 0.4515(3) -0.2941(7) 0.059(5) Uiso calc R 1 H
H8B 0.4506(3) 0.4649(3) -0.0796(7) 0.059(5) Uiso calc R 1 H
H8C 0.4661(3) 0.5758(3) -0.1935(7) 0.059(5) Uiso calc R 1 H
C11 0.4404(3) 0.1018(3) 0.1533(7) 0.0591(11) Uani d . 1 C
H11 0.4254(3) 0.0830(3) 0.2822(7) 0.105(9) Uiso calc R 1 H
C15 0.3768(5) 0.1172(4) -0.1491(7) 0.0723(14) Uani d . 1 C
H15 0.3165(5) 0.1073(4) -0.2319(7) 0.105(9) Uiso calc R 1 H
C12 0.5520(4) 0.1417(4) 0.0815(13) 0.093(2) Uani d . 1 C
H12 0.6126(4) 0.1488(4) 0.1612(13) 0.105(9) Uiso calc R 1 H
C13 0.5745(6) 0.1707(4) -0.1024(16) 0.116(3) Uani d . 1 C
H13 0.6510(6) 0.1991(4) -0.1503(16) 0.105(9) Uiso calc R 1 H
C14 0.4893(7) 0.1592(5) -0.2153(11) 0.114(3) Uani d . 1 C
H14 0.5059(7) 0.1801(5) -0.3433(11) 0.105(9) Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0249(10) 0.0354(11) 0.0381(12) 0.0074(9) -0.0029(10) 0.0046(10)
O2 0.0604(14) 0.0251(10) 0.0213(10) 0.0158(10) 0.0012(9) 0.0021(9)
O3 0.0667(15) 0.0315(11) 0.0352(12) 0.0280(11) -0.0058(11) -0.0058(10)
N1 0.0266(12) 0.0268(11) 0.0354(14) 0.0111(10) 0.0001(10) 0.0003(11)
C2 0.033(2) 0.033(2) 0.032(2) 0.0171(13) -0.0068(13) -0.0021(13)
C3 0.0285(13) 0.0286(14) 0.028(2) 0.0119(12) 0.0003(12) 0.0002(12)
C4 0.036(2) 0.035(2) 0.0232(14) 0.0190(13) 0.0028(12) -0.0001(12)
C6 0.036(2) 0.0261(14) 0.036(2) 0.0144(13) 0.0023(14) 0.0001(12)
C10 0.046(2) 0.029(2) 0.052(2) 0.0253(14) 0.005(2) 0.0037(15)
C9 0.038(2) 0.0271(14) 0.043(2) 0.0155(12) -0.0011(14) 0.0022(13)
C1 0.055(2) 0.055(2) 0.032(2) 0.035(2) -0.006(2) -0.001(2)
C5 0.070(2) 0.037(2) 0.030(2) 0.031(2) -0.010(2) -0.0077(14)
C7 0.054(2) 0.036(2) 0.034(2) 0.0212(15) 0.000(2) 0.0066(14)
C8 0.047(2) 0.053(2) 0.079(3) 0.027(2) 0.010(2) 0.005(2)
C11 0.045(2) 0.039(2) 0.090(3) 0.019(2) -0.016(2) -0.008(2)
C15 0.104(4) 0.092(3) 0.060(3) 0.078(3) 0.027(3) 0.017(2)
C12 0.044(2) 0.049(2) 0.188(8) 0.024(2) -0.013(4) -0.009(4)
C13 0.072(3) 0.050(3) 0.242(10) 0.041(3) 0.075(5) 0.036(4)
C14 0.151(6) 0.107(4) 0.137(6) 0.105(4) 0.099(5) 0.059(4)
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_publ_flag
N1 O1 H(O) 109.47(14) ?
C4 O2 C6 109.5(2) ?
C6 O3 C5 106.7(2) ?
O1 N1 C3 106.0(2) yes
O1 N1 C9 105.2(2) yes
C3 N1 C9 111.9(2) yes
C1 C2 C3 176.7(3) yes
N1 C3 C2 114.6(2) yes
N1 C3 C4 111.5(2) yes
C2 C3 C4 108.7(2) ?
N1 C3 H3 107.25(14) ?
C2 C3 H3 107.2(2) ?
C4 C3 H3 107.25(14) ?
O2 C4 C5 103.8(2) ?
O2 C4 C3 110.2(2) ?
C5 C4 C3 113.0(2) ?
O2 C4 H4 109.9(2) ?
C5 C4 H4 109.9(2) ?
C3 C4 H4 109.91(15) ?
O3 C6 O2 105.6(2) ?
O3 C6 C7 108.6(2) ?
O2 C6 C7 108.9(2) ?
O3 C6 C8 112.0(3) ?
O2 C6 C8 108.7(2) ?
C7 C6 C8 112.7(3) ?
C11 C10 C15 118.9(4) ?
C11 C10 C9 120.7(4) ?
C15 C10 C9 120.3(4) ?
N1 C9 C10 111.2(2) ?
N1 C9 H9A 109.4(2) ?
C10 C9 H9A 109.4(2) ?
N1 C9 H9B 109.4(2) ?
C10 C9 H9B 109.4(2) ?
H9A C9 H9B 108.0 ?
C2 C1 H1 180.0(12) ?
O3 C5 C4 103.7(3) ?
O3 C5 H5A 111.0(2) ?
C4 C5 H5A 111.0(2) ?
O3 C5 H5B 111.0(2) ?
C4 C5 H5B 111.0(2) ?
H5A C5 H5B 109.0 ?
C6 C7 H7A 109.5(2) ?
C6 C7 H7B 109.5(2) ?
H7A C7 H7B 109.5 ?
C6 C7 H7C 109.5(2) ?
H7A C7 H7C 109.5 ?
H7B C7 H7C 109.5 ?
C6 C8 H8A 109.5(2) ?
C6 C8 H8B 109.5(2) ?
H8A C8 H8B 109.5 ?
C6 C8 H8C 109.5(2) ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C10 C11 C12 119.9(5) ?
C10 C11 H11 120.0(3) ?
C12 C11 H11 120.0(4) ?
C10 C15 C14 119.7(6) ?
C10 C15 H15 120.1(3) ?
C14 C15 H15 120.1(4) ?
C13 C12 C11 120.3(6) ?
C13 C12 H12 119.9(4) ?
C11 C12 H12 119.9(4) ?
C14 C13 C12 120.0(5) ?
C14 C13 H13 120.0(4) ?
C12 C13 H13 120.0(4) ?
C13 C14 C15 121.1(6) ?
C13 C14 H14 119.5(4) ?
C15 C14 H14 119.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.455(3) yes
O1 H(O) 0.84 ?
O2 C4 1.421(4) yes
O2 C6 1.437(4) yes
O3 C6 1.415(4) yes
O3 C5 1.418(4) yes
N1 C3 1.471(4) yes
N1 C9 1.474(4) yes
C2 C1 1.170(5) yes
C2 C3 1.484(4) yes
C3 C4 1.530(4) yes
C3 H3 1.00 ?
C4 C5 1.526(4) yes
C4 H4 1.00 ?
C6 C7 1.508(5) ?
C6 C8 1.511(4) ?
C10 C11 1.365(5) ?
C10 C15 1.385(6) ?
C10 C9 1.509(4) ?
C9 H9A 0.99 ?
C9 H9B 0.99 ?
C1 H1 0.95 ?
C5 H5A 0.99 ?
C5 H5B 0.99 ?
C7 H7A 0.98 ?
C7 H7B 0.98 ?
C7 H7C 0.98 ?
C8 H8A 0.98 ?
C8 H8B 0.98 ?
C8 H8C 0.98 ?
C11 C12 1.395(8) ?
C11 H11 0.95 ?
C15 C14 1.388(8) ?
C15 H15 0.95 ?
C12 C13 1.362(11) ?
C12 H12 0.95 ?
C13 C14 1.333(12) ?
C13 H13 0.95 ?
C14 H14 0.95 ?
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_publ_flag
C2 C3 C4 C5 61.9(3) ?
C2 C3 C4 O2 177.4(2) yes
O2 C4 C3 N1 -55.3(3) yes
C3 N1 C9 C10 -68.9(4) yes
N1 C9 C10 C11 126.2(4) yes
C4 C5 O3 C6 -32.9(3) ?
C5 C4 O2 C6 -5.5(3) ?
C10 C11 C12 C13 1.2(6) ?
C11 C12 C13 C14 -1.1(8) ?
C12 C13 C14 C15 -0.4(8) ?