#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/18/2211815.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_2211815
loop_
_publ_author_name
'Naoual Laghrib'
'Mohamed Azrour'
'Jean-Claude Daran'
'Rachid Fihi'
'Lhou Majidi'
_publ_section_title
(1SR,3RS,5SR)-3-Hydroxy-3-(2-hydroxyethyl)-N-phenyl-5-(p-tolyl)pyrrolidin-2-one
_journal_coeditor_code           GK2037
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o402
_journal_page_last               o404
_journal_paper_doi               10.1107/S1600536806054961
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H21 N1 O3'
_chemical_formula_moiety         'C19 H21 N1 O3'
_chemical_formula_sum            'C19 H21 N O3'
_chemical_formula_weight         311.37
_chemical_name_systematic
;
(1SR,3RS,5SR)-3-Hydroxy-3-(2-hydroxyethyl)-N-phenyl-5-tolylpyrrolidin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 92.980(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7403(9)
_cell_length_b                   9.0806(11)
_cell_length_c                   30.836(4)
_cell_measurement_reflns_used    1615
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      32.2
_cell_measurement_theta_min      2.9
_cell_volume                     1605.2(4)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2003)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2003)
;
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2003)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 8.2632
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'ω and φ'
_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  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12229
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.31
_diffrn_reflns_theta_min         2.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0551
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0768P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                2044
_reflns_number_total             3291
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2037.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C19 H21 N1 O3'
_cod_database_code               2211815
_cod_database_fobs_code          2211815
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
N N1 0.4274(4) 0.4096(2) 0.65441(7) 0.0188(5) Uani d . 1
O O1 0.7526(3) 0.3432(2) 0.69634(6) 0.0236(5) Uani d . 1
O O2 0.7831(3) 0.6477(2) 0.70648(6) 0.0268(5) Uani d . 1
H H2 0.7865 0.7229 0.7224 0.040 Uiso calc R 1
O O3 0.1805(3) 0.3870(2) 0.74263(6) 0.0257(5) Uani d . 1
H H3 0.0441 0.3956 0.7317 0.039 Uiso calc R 1
C C1 0.5951(5) 0.4304(3) 0.68631(9) 0.0204(6) Uani d . 1
C C2 0.5617(5) 0.5790(3) 0.70784(9) 0.0200(6) Uani d . 1
C C3 0.3783(5) 0.6531(3) 0.67776(9) 0.0231(7) Uani d . 1
H H3A 0.4528 0.7221 0.6578 0.028 Uiso calc R 1
H H3B 0.2661 0.7087 0.6948 0.028 Uiso calc R 1
C C4 0.2534(5) 0.5285(3) 0.65201(9) 0.0189(6) Uani d . 1
H H4 0.1117 0.4973 0.6672 0.023 Uiso calc R 1
C C21 0.4992(5) 0.5585(3) 0.75537(9) 0.0235(7) Uani d . 1
H H21A 0.5986 0.4788 0.7681 0.028 Uiso calc R 1
H H21B 0.5416 0.6501 0.7713 0.028 Uiso calc R 1
C C22 0.2500(5) 0.5227(3) 0.76379(10) 0.0267(7) Uani d . 1
H H22A 0.2325 0.5135 0.7954 0.032 Uiso calc R 1
H H22B 0.1475 0.6037 0.7528 0.032 Uiso calc R 1
C C111 0.3902(5) 0.2681(3) 0.63444(9) 0.0200(6) Uani d . 1
C C112 0.5592(5) 0.2091(3) 0.60981(10) 0.0275(7) Uani d . 1
H H112 0.6968 0.2638 0.6051 0.033 Uiso calc R 1
C C113 0.5300(6) 0.0695(4) 0.59164(11) 0.0339(8) Uani d . 1
H H113 0.6470 0.0290 0.5745 0.041 Uiso calc R 1
C C114 0.3309(6) -0.0095(3) 0.59858(10) 0.0327(8) Uani d . 1
H H114 0.3102 -0.1051 0.5865 0.039 Uiso calc R 1
C C115 0.1618(6) 0.0509(3) 0.62322(10) 0.0324(8) Uani d . 1
H H115 0.0246 -0.0040 0.6280 0.039 Uiso calc R 1
C C116 0.1880(5) 0.1902(3) 0.64113(10) 0.0270(7) Uani d . 1
H H116 0.0693 0.2315 0.6577 0.032 Uiso calc R 1
C C411 0.1834(5) 0.5747(3) 0.60595(9) 0.0199(6) Uani d . 1
C C412 -0.0339(5) 0.6402(3) 0.59822(10) 0.0271(7) Uani d . 1
H H412 -0.1395 0.6463 0.6209 0.033 Uiso calc R 1
C C413 -0.0968(5) 0.6971(3) 0.55729(10) 0.0304(8) Uani d . 1
H H413 -0.2453 0.7421 0.5525 0.036 Uiso calc R 1
C C414 0.0513(6) 0.6895(3) 0.52351(10) 0.0280(7) Uani d . 1
C C415 0.2641(5) 0.6223(3) 0.53144(10) 0.0272(7) Uani d . 1
H H415 0.3679 0.6142 0.5086 0.033 Uiso calc R 1
C C416 0.3305(5) 0.5662(3) 0.57196(9) 0.0243(7) Uani d . 1
H H416 0.4793 0.5213 0.5765 0.029 Uiso calc R 1
C C417 -0.0190(6) 0.7536(4) 0.47962(10) 0.0451(9) Uani d . 1
H H41A 0.0536 0.8505 0.4767 0.068 Uiso calc R 1
H H41B -0.1890 0.7638 0.4769 0.068 Uiso calc R 1
H H41C 0.0329 0.6881 0.4568 0.068 Uiso calc R 1
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
C1 N1 C111 121.4(2)
C1 N1 C4 113.0(2)
C111 N1 C4 123.4(2)
C2 O2 H2 109.5
C22 O3 H3 109.5
O1 C1 N1 125.4(3)
O1 C1 C2 124.7(2)
N1 C1 C2 109.9(2)
O2 C2 C1 104.1(2)
O2 C2 C3 112.3(2)
C1 C2 C3 103.0(2)
O2 C2 C21 109.6(2)
C1 C2 C21 110.5(2)
C3 C2 C21 116.5(2)
C2 C3 C4 106.1(2)
C2 C3 H3A 110.5
C4 C3 H3A 110.5
C2 C3 H3B 110.5
C4 C3 H3B 110.5
H3A C3 H3B 108.7
N1 C4 C411 113.4(2)
N1 C4 C3 102.5(2)
C411 C4 C3 111.9(2)
N1 C4 H4 109.6
C411 C4 H4 109.6
C3 C4 H4 109.6
C22 C21 C2 117.5(2)
C22 C21 H21A 107.9
C2 C21 H21A 107.9
C22 C21 H21B 107.9
C2 C21 H21B 107.9
H21A C21 H21B 107.2
O3 C22 C21 110.5(2)
O3 C22 H22A 109.6
C21 C22 H22A 109.6
O3 C22 H22B 109.6
C21 C22 H22B 109.6
H22A C22 H22B 108.1
C112 C111 C116 120.4(3)
C112 C111 N1 119.5(2)
C116 C111 N1 120.0(2)
C111 C112 C113 120.3(3)
C111 C112 H112 119.9
C113 C112 H112 119.9
C114 C113 C112 119.7(3)
C114 C113 H113 120.1
C112 C113 H113 120.1
C113 C114 C115 119.6(3)
C113 C114 H114 120.2
C115 C114 H114 120.2
C114 C115 C116 121.2(3)
C114 C115 H115 119.4
C116 C115 H115 119.4
C111 C116 C115 118.8(3)
C111 C116 H116 120.6
C115 C116 H116 120.6
C416 C411 C412 118.1(3)
C416 C411 C4 123.6(3)
C412 C411 C4 118.1(3)
C411 C412 C413 120.1(3)
C411 C412 H412 120.0
C413 C412 H412 120.0
C414 C413 C412 121.6(3)
C414 C413 H413 119.2
C412 C413 H413 119.2
C415 C414 C413 117.7(3)
C415 C414 C417 121.6(3)
C413 C414 C417 120.7(3)
C414 C415 C416 121.6(3)
C414 C415 H415 119.2
C416 C415 H415 119.2
C411 C416 C415 120.9(3)
C411 C416 H416 119.5
C415 C416 H416 119.5
C414 C417 H41A 109.5
C414 C417 H41B 109.5
H41A C417 H41B 109.5
C414 C417 H41C 109.5
H41A C417 H41C 109.5
H41B C417 H41C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.353(4)
N1 C111 1.436(3)
N1 C4 1.470(3)
O1 C1 1.229(3)
O2 C2 1.419(3)
O2 H2 0.8400
O3 C22 1.441(3)
O3 H3 0.8400
C1 C2 1.520(4)
C2 C3 1.523(4)
C2 C21 1.538(4)
C3 C4 1.539(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C411 1.515(4)
C4 H4 1.0000
C21 C22 1.503(4)
C21 H21A 0.9900
C21 H21B 0.9900
C22 H22A 0.9900
C22 H22B 0.9900
C111 C112 1.372(4)
C111 C116 1.384(4)
C112 C113 1.393(4)
C112 H112 0.9500
C113 C114 1.375(4)
C113 H113 0.9500
C114 C115 1.377(4)
C114 H114 0.9500
C115 C116 1.385(4)
C115 H115 0.9500
C116 H116 0.9500
C411 C416 1.382(4)
C411 C412 1.392(4)
C412 C413 1.394(4)
C412 H412 0.9500
C413 C414 1.380(4)
C413 H413 0.9500
C414 C415 1.376(4)
C414 C417 1.509(4)
C415 C416 1.384(4)
C415 H415 0.9500
C416 H416 0.9500
C417 H41A 0.9800
C417 H41B 0.9800
C417 H41C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O3 H3 O1 1_455 0.84 2.01 2.804(3) 159
O2 H2 O3 2_656 0.84 1.84 2.682(3) 175
