#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502872.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_1502872
loop_
_publ_author_name
'Solomon, Marissa R.'
'Sivaguru, J.'
'Jockusch, Steffen'
'Adam, Waldemar'
'Turro, Nicholas J.'
_publ_section_title
;
 Decoding stereocontrol during the photooxygenation of
 oxazolidinone-functionalized enecarbamates.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2142
_journal_page_last               2145
_journal_paper_doi               10.1021/ol100174r
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 102.867(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.425(5)
_cell_length_b                   8.0342(19)
_cell_length_c                   11.639(3)
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.40
_cell_volume                     1862.0(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0891
_diffrn_reflns_av_sigmaI/netI    0.1283
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14797
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         5668
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1623
_refine_ls_R_factor_gt           0.0711
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1780
_reflns_number_gt                2830
_reflns_number_total             5668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100174r_si_002.cif
_cod_data_source_block           mss10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1861.9(8)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1502872
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.20861(10) 0.3611(3) -0.10160(18) 0.0380(6) Uani 1 1 d .
O2 O 0.20748(11) 0.3110(3) 0.0879(2) 0.0460(6) Uani 1 1 d .
N1 N 0.30706(12) 0.3388(3) 0.0261(2) 0.0330(6) Uani 1 1 d .
C1 C 0.23831(15) 0.3339(4) 0.0123(3) 0.0324(7) Uani 1 1 d .
C2 C 0.32417(16) 0.3299(4) -0.0903(3) 0.0369(7) Uani 1 1 d .
H2A H 0.3314 0.2113 -0.1105 0.044 Uiso 1 1 calc R
C3 C 0.25928(16) 0.3943(4) -0.1675(3) 0.0419(8) Uani 1 1 d .
H3A H 0.2624 0.5151 -0.1822 0.050 Uiso 1 1 calc R
H3B H 0.2489 0.3353 -0.2441 0.050 Uiso 1 1 calc R
C4 C 0.38549(17) 0.4321(5) -0.0964(3) 0.0478(9) Uani 1 1 d .
H4A H 0.4252 0.3832 -0.0444 0.072 Uiso 1 1 calc R
H4B H 0.3794 0.5464 -0.0712 0.072 Uiso 1 1 calc R
H4C H 0.3916 0.4330 -0.1776 0.072 Uiso 1 1 calc R
C5 C 0.34930(15) 0.2516(4) 0.1216(3) 0.0332(7) Uani 1 1 d .
H5A H 0.3505 0.1336 0.1179 0.040 Uiso 1 1 calc R
C6 C 0.38694(14) 0.3267(4) 0.2151(2) 0.0285(6) Uani 1 1 d .
C7 C 0.43239(15) 0.2236(4) 0.3116(3) 0.0309(7) Uani 1 1 d .
H7A H 0.4464 0.2992 0.3810 0.037 Uiso 1 1 calc R
C8 C 0.39496(17) 0.0789(4) 0.3529(3) 0.0371(8) Uani 1 1 d .
H8A H 0.4256 0.0179 0.4155 0.056 Uiso 1 1 calc R
H8B H 0.3781 0.0039 0.2865 0.056 Uiso 1 1 calc R
H8C H 0.3572 0.1220 0.3830 0.056 Uiso 1 1 calc R
C9 C 0.38689(15) 0.5118(4) 0.2336(3) 0.0333(7) Uani 1 1 d .
H9A H 0.3518 0.5604 0.1684 0.040 Uiso 1 1 calc R
C10 C 0.45461(17) 0.5891(4) 0.2261(3) 0.0443(9) Uani 1 1 d .
H10A H 0.4647 0.5613 0.1499 0.066 Uiso 1 1 calc R
H10B H 0.4900 0.5450 0.2899 0.066 Uiso 1 1 calc R
H10C H 0.4523 0.7103 0.2337 0.066 Uiso 1 1 calc R
C11 C 0.49683(15) 0.1611(4) 0.2814(3) 0.0314(7) Uani 1 1 d .
C12 C 0.49624(17) 0.0480(4) 0.1906(3) 0.0394(8) Uani 1 1 d .
H12A H 0.4548 0.0174 0.1399 0.047 Uiso 1 1 calc R
C13 C 0.55586(18) -0.0204(4) 0.1735(3) 0.0426(9) Uani 1 1 d .
H13A H 0.5547 -0.0981 0.1115 0.051 Uiso 1 1 calc R
C14 C 0.61649(17) 0.0232(4) 0.2454(3) 0.0437(9) Uani 1 1 d .
H14A H 0.6569 -0.0261 0.2342 0.052 Uiso 1 1 calc R
C15 C 0.61842(16) 0.1387(5) 0.3336(3) 0.0454(9) Uani 1 1 d .
H15A H 0.6602 0.1704 0.3827 0.054 Uiso 1 1 calc R
C16 C 0.55920(15) 0.2082(4) 0.3503(3) 0.0372(8) Uani 1 1 d .
H16A H 0.5610 0.2899 0.4100 0.045 Uiso 1 1 calc R
C17 C 0.36632(15) 0.5504(4) 0.3497(3) 0.0339(7) Uani 1 1 d .
C18 C 0.40257(17) 0.6521(4) 0.4359(3) 0.0409(8) Uani 1 1 d .
H18A H 0.4427 0.7017 0.4238 0.049 Uiso 1 1 calc R
C19 C 0.38260(19) 0.6845(4) 0.5393(3) 0.0469(9) Uani 1 1 d .
H19A H 0.4087 0.7558 0.5969 0.056 Uiso 1 1 calc R
C20 C 0.32387(19) 0.6121(5) 0.5590(3) 0.0485(10) Uani 1 1 d .
H20A H 0.3095 0.6341 0.6298 0.058 Uiso 1 1 calc R
C21 C 0.28711(18) 0.5085(5) 0.4746(3) 0.0445(9) Uani 1 1 d .
H21A H 0.2475 0.4573 0.4876 0.053 Uiso 1 1 calc R
C22 C 0.30763(16) 0.4784(4) 0.3706(3) 0.0381(8) Uani 1 1 d .
H22A H 0.2814 0.4078 0.3126 0.046 Uiso 1 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
C1 O1 C3 109.5(2)
C1 N1 C5 120.0(2)
C1 N1 C2 109.6(2)
C5 N1 C2 117.7(2)
O2 C1 O1 123.3(3)
O2 C1 N1 127.1(3)
O1 C1 N1 109.5(2)
N1 C2 C4 112.6(3)
N1 C2 C3 100.0(2)
C4 C2 C3 114.2(3)
O1 C3 C2 104.9(2)
C6 C5 N1 123.6(3)
C5 C6 C9 123.2(3)
C5 C6 C7 120.1(3)
C9 C6 C7 116.7(3)
C11 C7 C8 110.0(3)
C11 C7 C6 115.0(2)
C8 C7 C6 112.2(2)
C6 C9 C17 109.6(3)
C6 C9 C10 111.2(3)
C17 C9 C10 113.3(3)
C12 C11 C16 117.7(3)
C12 C11 C7 122.0(3)
C16 C11 C7 120.2(3)
C13 C12 C11 120.5(3)
C14 C13 C12 120.7(3)
C13 C14 C15 119.8(3)
C14 C15 C16 119.7(3)
C15 C16 C11 121.5(3)
C18 C17 C22 117.5(3)
C18 C17 C9 123.6(3)
C22 C17 C9 118.9(3)
C17 C18 C19 122.2(3)
C18 C19 C20 119.8(3)
C21 C20 C19 119.1(3)
C20 C21 C22 120.4(3)
C21 C22 C17 121.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.347(4)
O1 C3 1.444(4)
O2 C1 1.205(4)
N1 C1 1.378(4)
N1 C5 1.429(4)
N1 C2 1.475(4)
C2 C4 1.512(5)
C2 C3 1.517(4)
C5 C6 1.329(4)
C6 C9 1.503(4)
C6 C7 1.532(4)
C7 C11 1.521(4)
C7 C8 1.526(4)
C9 C17 1.533(4)
C9 C10 1.536(4)
C11 C12 1.392(4)
C11 C16 1.398(4)
C12 C13 1.391(4)
C13 C14 1.377(5)
C14 C15 1.377(5)
C15 C16 1.385(4)
C17 C18 1.375(4)
C17 C22 1.400(4)
C18 C19 1.378(5)
C19 C20 1.398(5)
C20 C21 1.376(5)
C21 C22 1.387(5)
