#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/45/2014571.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_2014571
loop_
_publ_author_name
'Tracey, Michael R.'
'Grebe, Tyler P.'
'Brennessel, William W.'
'Hsung, Richard P.'
_publ_section_title
;
 (4R)-3-Allenyl-4-(diphenylmethyl)oxazolidin-2-one, an
 unsubstituted allenamide
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o830
_journal_page_last               o832
_journal_paper_doi               10.1107/S0108270104023121
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C19 H17 N O2'
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.34
_chemical_name_common
(4R)-3-Allenyl-4-(diphenylmethyl)oxazolidin-2-one
_chemical_name_systematic        ?
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 98.281(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2531(10)
_cell_length_b                   13.738(2)
_cell_length_c                   8.8997(14)
_cell_measurement_reflns_used    1550
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      2.31
_cell_volume                     756.6(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4418
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         1406
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0337
_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)+(0.0403P)²+0.0499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                1231
_reflns_number_total             1406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sx1144.cif
_cod_data_source_block           7a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multi-scans' was replaced
with the value 'multi-scan' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2014571
_cod_database_fobs_code          2014571
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.2813(3) 0.34256(16) 0.2904(3) 0.0605(6) Uani d . 1 . . O
O2 0.5406(3) 0.34983(14) 0.4936(2) 0.0514(5) Uani d . 1 . . O
N1 0.6177(3) 0.27542(15) 0.2879(2) 0.0375(5) Uani d . 1 . . N
C1 0.8930(6) 0.2308(3) -0.0383(4) 0.0550(8) Uani d . 1 . . C
H1A 0.967(6) 0.287(3) -0.095(4) 0.089(12) Uiso d . 1 . . H
H1B 0.943(6) 0.161(3) -0.059(5) 0.090(12) Uiso d . 1 . . H
C2 0.7485(5) 0.24623(19) 0.0490(3) 0.0410(6) Uani d . 1 . . C
C3 0.5943(4) 0.2571(2) 0.1300(3) 0.0439(7) Uani d . 1 . . C
H3A 0.4509 0.2524 0.0782 0.053 Uiso calc R 1 . . H
C4 0.4641(5) 0.32383(19) 0.3496(3) 0.0454(7) Uani d . 1 . . C
C5 0.7700(4) 0.33048(19) 0.5217(3) 0.0442(7) Uani d . 1 . . C
H5A 0.8116 0.3022 0.6240 0.053 Uiso calc R 1 . . H
H5B 0.8535 0.3911 0.5139 0.053 Uiso calc R 1 . . H
C6 0.8113(4) 0.25813(18) 0.3993(3) 0.0348(6) Uani d . 1 . . C
H6A 0.9460 0.2747 0.3563 0.042 Uiso calc R 1 . . H
C7 0.8180(4) 0.15216(17) 0.4590(3) 0.0332(6) Uani d . 1 . . C
H7A 0.6836 0.1417 0.5057 0.040 Uiso calc R 1 . . H
C8 1.0100(4) 0.13262(18) 0.5827(3) 0.0354(6) Uani d . 1 . . C
C9 1.0122(5) 0.04589(18) 0.6632(3) 0.0434(7) Uani d . 1 . . C
H9A 0.8921 0.0030 0.6451 0.052 Uiso calc R 1 . . H
C10 1.1882(5) 0.0213(2) 0.7698(3) 0.0535(8) Uani d . 1 . . C
H10A 1.1892 -0.0388 0.8225 0.064 Uiso calc R 1 . . H
C11 1.3627(5) 0.0840(3) 0.7997(3) 0.0566(8) Uani d . 1 . . C
H11A 1.4833 0.0671 0.8726 0.068 Uiso calc R 1 . . H
C12 1.3596(5) 0.1706(2) 0.7233(3) 0.0546(8) Uani d . 1 . . C
H12A 1.4777 0.2143 0.7450 0.066 Uiso calc R 1 . . H
C13 1.1868(4) 0.1952(2) 0.6149(3) 0.0438(7) Uani d . 1 . . C
H13A 1.1883 0.2552 0.5619 0.053 Uiso calc R 1 . . H
C14 0.8155(4) 0.07853(16) 0.3323(3) 0.0351(6) Uani d . 1 . . C
C15 0.6343(5) 0.0217(2) 0.2869(3) 0.0484(7) Uani d . 1 . . C
H15A 0.5127 0.0268 0.3393 0.058 Uiso calc R 1 . . H
C16 0.6284(6) -0.0426(2) 0.1655(4) 0.0623(9) Uani d . 1 . . C
H16A 0.5033 -0.0810 0.1352 0.075 Uiso calc R 1 . . H
C17 0.8022(6) -0.0502(2) 0.0906(4) 0.0633(10) Uani d . 1 . . C
H17A 0.7968 -0.0926 0.0057 0.076 Uiso calc R 1 . . H
C18 0.9860(6) 0.0031(2) 0.1371(4) 0.0591(9) Uani d . 1 . . C
H18A 1.1087 -0.0039 0.0863 0.071 Uiso calc R 1 . . H
C19 0.9925(5) 0.06699(19) 0.2577(3) 0.0460(7) Uani d . 1 . . C
H19A 1.1203 0.1033 0.2895 0.055 Uiso calc R 1 . . H
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C4 O2 C5 108.8(2) ?
C4 N1 C3 121.0(2) y
C4 N1 C6 111.8(2) y
C3 N1 C6 126.8(2) y
C2 C1 H1A 124(2) ?
C2 C1 H1B 121(2) ?
H1A C1 H1B 115(3) ?
C1 C2 C3 175.6(3) y
C2 C3 N1 126.6(2) y
C2 C3 H3A 116.7 ?
N1 C3 H3A 116.7 ?
O1 C4 N1 127.5(3) ?
O1 C4 O2 122.6(3) ?
N1 C4 O2 109.9(2) ?
O2 C5 C6 105.2(2) ?
O2 C5 H5A 110.7 ?
C6 C5 H5A 110.7 ?
O2 C5 H5B 110.7 ?
C6 C5 H5B 110.7 ?
H5A C5 H5B 108.8 ?
N1 C6 C5 99.7(2) ?
N1 C6 C7 111.3(2) y
C5 C6 C7 111.5(2) ?
N1 C6 H6A 111.3 ?
C5 C6 H6A 111.3 ?
C7 C6 H6A 111.3 ?
C14 C7 C8 109.97(19) ?
C14 C7 C6 112.1(2) ?
C8 C7 C6 113.1(2) ?
C14 C7 H7A 107.1 ?
C8 C7 H7A 107.1 ?
C6 C7 H7A 107.1 ?
C9 C8 C13 118.2(2) ?
C9 C8 C7 118.0(2) ?
C13 C8 C7 123.7(2) ?
C10 C9 C8 120.6(3) ?
C10 C9 H9A 119.7 ?
C8 C9 H9A 119.7 ?
C11 C10 C9 120.4(3) ?
C11 C10 H10A 119.8 ?
C9 C10 H10A 119.8 ?
C12 C11 C10 119.4(3) ?
C12 C11 H11A 120.3 ?
C10 C11 H11A 120.3 ?
C11 C12 C13 120.8(3) ?
C11 C12 H12A 119.6 ?
C13 C12 H12A 119.6 ?
C12 C13 C8 120.6(3) ?
C12 C13 H13A 119.7 ?
C8 C13 H13A 119.7 ?
C19 C14 C15 118.3(3) ?
C19 C14 C7 120.8(2) ?
C15 C14 C7 120.9(2) ?
C14 C15 C16 120.8(3) ?
C14 C15 H15A 119.6 ?
C16 C15 H15A 119.6 ?
C17 C16 C15 119.8(3) ?
C17 C16 H16A 120.1 ?
C15 C16 H16A 120.1 ?
C16 C17 C18 120.2(3) ?
C16 C17 H17A 119.9 ?
C18 C17 H17A 119.9 ?
C17 C18 C19 120.1(3) ?
C17 C18 H18A 119.9 ?
C19 C18 H18A 119.9 ?
C14 C19 C18 120.7(3) ?
C14 C19 H19A 119.7 ?
C18 C19 H19A 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.215(3) ?
O2 C4 . 1.350(4) ?
O2 C5 . 1.445(3) ?
N1 C4 . 1.349(3) y
N1 C3 . 1.414(4) y
N1 C6 . 1.469(3) y
C1 C2 . 1.291(5) y
C1 H1A . 1.06(4) ?
C1 H1B . 1.04(4) ?
C2 C3 . 1.292(4) y
C3 H3A . 0.9500 ?
C3 C15 . 3.517(4) ?
C5 C6 . 1.524(4) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.549(3) ?
C6 H6A . 1.0000 ?
C7 C14 . 1.514(3) ?
C7 C8 . 1.531(3) ?
C7 H7A . 1.0000 ?
C8 C9 . 1.389(4) ?
C8 C13 . 1.397(4) ?
C9 C10 . 1.387(4) ?
C9 H9A . 0.9500 ?
C10 C11 . 1.385(5) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.369(5) ?
C11 H11A . 0.9500 ?
C12 C13 . 1.383(4) ?
C12 H12A . 0.9500 ?
C13 H13A . 0.9500 ?
C14 C19 . 1.379(4) ?
C14 C15 . 1.387(4) ?
C15 C16 . 1.392(4) ?
C15 H15A . 0.9500 ?
C16 C17 . 1.359(5) ?
C16 H16A . 0.9500 ?
C17 C18 . 1.376(5) ?
C17 H17A . 0.9500 ?
C18 C19 . 1.382(4) ?
C18 H18A . 0.9500 ?
C19 H19A . 0.9500 ?
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
C6 H6A O1 1_655 1.00 2.44 3.427(3) 168
C9 H9A O1 2_646 0.95 2.56 3.400(4) 148
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
C1 C2 C3 N1 148(4) ?
C4 N1 C3 C2 152.3(3) ?
C6 N1 C3 C2 -19.1(4) y
C3 N1 C4 O1 13.2(4) ?
C6 N1 C4 O1 -174.2(3) ?
C3 N1 C4 O2 -167.4(2) ?
C6 N1 C4 O2 5.2(3) ?
C5 O2 C4 O1 -171.3(2) ?
C5 O2 C4 N1 9.2(3) ?
C4 O2 C5 C6 -19.2(3) ?
C4 N1 C6 C5 -16.1(3) ?
C3 N1 C6 C5 156.0(2) ?
C4 N1 C6 C7 101.7(2) ?
C3 N1 C6 C7 -86.2(3) ?
O2 C5 C6 N1 20.3(2) ?
O2 C5 C6 C7 -97.2(2) ?
N1 C6 C7 C14 58.6(3) ?
C5 C6 C7 C14 169.0(2) ?
N1 C6 C7 C8 -176.4(2) ?
C5 C6 C7 C8 -66.1(3) ?
C14 C7 C8 C9 -65.0(3) ?
C6 C7 C8 C9 169.0(2) ?
C14 C7 C8 C13 112.4(3) ?
C6 C7 C8 C13 -13.7(3) ?
C13 C8 C9 C10 -1.6(4) ?
C7 C8 C9 C10 175.8(2) ?
C8 C9 C10 C11 1.3(4) ?
C9 C10 C11 C12 0.1(4) ?
C10 C11 C12 C13 -1.2(5) ?
C11 C12 C13 C8 0.9(4) ?
C9 C8 C13 C12 0.5(4) ?
C7 C8 C13 C12 -176.8(2) ?
C8 C7 C14 C19 -56.1(3) ?
C6 C7 C14 C19 70.5(3) ?
C8 C7 C14 C15 124.6(2) ?
C6 C7 C14 C15 -108.7(3) ?
C19 C14 C15 C16 -2.4(4) ?
C7 C14 C15 C16 176.9(2) ?
C14 C15 C16 C17 0.2(4) ?
C15 C16 C17 C18 2.0(5) ?
C16 C17 C18 C19 -1.9(5) ?
C15 C14 C19 C18 2.4(4) ?
C7 C14 C19 C18 -176.8(2) ?
C17 C18 C19 C14 -0.3(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181230
