#------------------------------------------------------------------------------
#$Date: 2017-01-17 16:22:02 +0200 (Tue, 17 Jan 2017) $
#$Revision: 190596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/38/2003849.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_2003849
loop_
_publ_author_name
'Chiaroni, A.'
'Riche, C.'
'Nicole, L.'
_publ_section_title
(2R,3S,4S)-3-Hydroxy-4-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-2-methanol
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1859
_journal_page_last               1861
_journal_paper_doi               10.1107/S0108270194015027
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C14 H21 N O2'
_chemical_formula_sum            'C14 H21 N O2'
_chemical_formula_weight         235.33
_chemical_name_systematic
;
(2R,3S,4S) 1-[(1S)-1-phenylethyl]-3-hydroxy-2-hydroxymethyl-4-methyl
pyrrolidine
;
_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_type_scat_source           'International Tables Vol. IV Table 2.2B'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.593(4)
_cell_length_b                   10.237(5)
_cell_length_c                   20.219(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      14.9
_cell_volume                     1364.6(13)
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1987)'
_computing_data_reduction        'NONIUS (Riche, 1989)'
_computing_molecular_graphics
;
R3M (Riche, 1983) and ORTEP (Johnson, 1965)
;
_computing_publication_material  'ACTACIF (Riche, 1992)'
_computing_structure_refinement  'SHELX76 (Sheldrick, 1976)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4724
_diffrn_reflns_theta_max         65.84
_diffrn_reflns_theta_min         4.32
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.57
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.15
_exptl_crystal_description       prism
_exptl_crystal_F_000             512.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.64
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2242
_refine_ls_R_factor_obs          0.036
_refine_ls_shift/esd_max         0.02
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0003F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          2244
_reflns_number_total             2368
_reflns_observed_criterion       refl_observed_if_I_>_3.0_sigma(I)
_cod_data_source_file            ab1230.cif
_cod_data_source_block           pyrrolidine
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-17

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(F) +
0.0003F^2^]' 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^(F) + 0.0003F^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1364.6(12)
_cod_database_code               2003849
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
N1 N 0.7732(2) 0.5662(1) 0.1626(1) 0.045(1) Uani ? ?
C2 C 0.6869(2) 0.6186(2) 0.1002(1) 0.047(1) Uani ? ?
C3 C 0.7931(2) 0.5466(2) 0.0444(1) 0.052(1) Uani ? ?
C4 C 0.8657(2) 0.4207(2) 0.0770(1) 0.053(1) Uani ? ?
C5 C 0.9303(2) 0.4708(2) 0.1441(1) 0.049(1) Uani ? ?
C6 C 0.4591(2) 0.5961(2) 0.1014(1) 0.053(1) Uani ? ?
O7 O 0.3676(2) 0.6608(1) 0.0468(1) 0.060(1) Uani ? ?
O8 O 0.9675(2) 0.6166(1) 0.0212(1) 0.062(1) Uani ? ?
C9 C 1.0233(3) 0.3422(2) 0.0396(1) 0.070(2) Uani ? ?
C10 C 0.8455(2) 0.6648(2) 0.2098(1) 0.049(1) Uani ? ?
C11 C 0.6774(3) 0.7594(2) 0.2301(1) 0.072(2) Uani ? ?
C12 C 0.9293(2) 0.5995(1) 0.2711(1) 0.050(1) Uani ? ?
C13 C 0.8126(3) 0.5117(2) 0.3070(1) 0.068(2) Uani ? ?
C14 C 0.8872(5) 0.4572(2) 0.3648(1) 0.089(3) Uani ? ?
C15 C 1.0751(5) 0.4897(2) 0.3873(1) 0.094(3) Uani ? ?
C16 C 1.1954(4) 0.5758(3) 0.3519(1) 0.084(2) Uani ? ?
C17 C 1.1210(3) 0.6302(2) 0.2936(1) 0.061(2) Uani ? ?
HO7 H 0.239(3) 0.642(2) 0.044(1) 0.076(6) Uiso ? ?
HO8 H 0.922(3) 0.695(2) -0.002(1) 0.082(6) Uiso ? ?
H2 H 0.70850 0.71458 0.09435 0.051 Uiso calc C2
H3 H 0.70113 0.53393 0.00559 0.057 Uiso calc C3
H4 H 0.75874 0.35148 0.07876 0.059 Uiso calc C4
H5a H 0.93617 0.39792 0.17698 0.053 Uiso calc C5
H5b H 1.06628 0.51378 0.14148 0.053 Uiso calc C5
H6a H 0.40152 0.63112 0.14355 0.058 Uiso calc C6
H6b H 0.43064 0.50029 0.09857 0.058 Uiso calc C6
H9a H 1.05909 0.26227 0.06554 0.077 Uiso calc C9
H9b H 0.96729 0.31579 -0.00439 0.077 Uiso calc C9
H9c H 1.14756 0.39658 0.03292 0.077 Uiso calc C9
H10 H 0.95461 0.71553 0.18696 0.054 Uiso calc C10
H11a H 0.73278 0.82477 0.26210 0.079 Uiso calc C11
H11b H 0.62500 0.80573 0.19004 0.079 Uiso calc C11
H11c H 0.56444 0.70972 0.25142 0.079 Uiso calc C11
H13 H 0.67382 0.48783 0.29109 0.075 Uiso calc C13
H14 H 0.80248 0.39339 0.39009 0.098 Uiso calc C14
H15 H 1.12649 0.45119 0.42953 0.103 Uiso calc C15
H16 H 1.33444 0.59869 0.36800 0.093 Uiso calc C16
H17 H 1.20740 0.69231 0.26781 0.067 Uiso calc C17
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 1 2
1 0 7
1 -4 3
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
C2 N1 C5 107.10(10) yes
C2 N1 C10 115.30(10) yes
C5 N1 C10 113.10(10) yes
N1 C2 C3 106.20(10) yes
N1 C2 C6 108.10(10) yes
C3 C2 C6 113.10(10) yes
C2 C3 C4 103.50(10) yes
C2 C3 O8 111.70(10) yes
C4 C3 O8 108.20(10) yes
C3 C4 C5 100.90(10) yes
C3 C4 C9 116.60(10) yes
C5 C4 C9 115.80(10) yes
N1 C5 C4 104.80(10) yes
C2 C6 O7 109.70(10) yes
N1 C10 C11 112.00(10) yes
N1 C10 C12 110.30(10) yes
C11 C10 C12 108.90(10) yes
C10 C12 C13 120.80(10) yes
C10 C12 C17 120.30(10) yes
C13 C12 C17 118.9(2) no
C12 C13 C14 120.4(2) no
C13 C14 C15 120.4(2) no
C14 C15 C16 120.3(2) no
C15 C16 C17 119.3(2) no
C12 C17 C16 120.7(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.484(2) yes
N1 C5 1.471(2) yes
N1 C10 1.468(2) yes
C2 C3 1.519(2) yes
C2 C6 1.520(2) yes
C3 C4 1.525(2) yes
C3 O8 1.434(2) yes
C4 C5 1.513(2) yes
C4 C9 1.515(3) yes
C6 O7 1.421(2) yes
C10 C11 1.528(3) yes
C10 C12 1.513(2) yes
C12 C13 1.388(2) no
C12 C17 1.380(2) no
C13 C14 1.385(3) no
C14 C15 1.361(5) no
C15 C16 1.386(4) no
C16 C17 1.392(3) no
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
C5 N1 C2 C3 2.30(10) yes
N1 C2 C3 C4 23.10(10) yes
C2 C3 C4 C5 -38.60(10) yes
C3 C4 C5 N1 40.70(10) yes
C4 C5 N1 C2 -27.10(10) yes
C2 N1 C10 C12 179.9(2) yes
N1 C10 C12 C13 -54.9(2) yes
N1 C2 C6 O7 172.0(2) yes
