#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:17:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/53/1555348.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_1555348
loop_
_publ_author_name
'Wright, Stephen W.'
'Choi, Chulho'
'Chung, Seungwon'
'Boscoe, Brian P.'
'Drozda, Susan E.'
'Mousseau, James J.'
'Trzupek, John D.'
_publ_section_title
;
 Reversal of Diastereoselection in the Conjugate Addition of Cuprates to
 Unsaturated Lactams.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5204
_journal_page_last               5207
_journal_paper_doi               10.1021/acs.orglett.5b02533
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_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                 92.9400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2360(4)
_cell_length_b                   6.3687(3)
_cell_length_c                   10.9331(5)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      31.08
_cell_measurement_theta_min      3.02
_cell_volume                     572.71(5)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 5.2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Triumph graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14199
_diffrn_reflns_theta_full        30.99
_diffrn_reflns_theta_max         30.99
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9626
_exptl_absorpt_correction_T_min  0.9403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0413
_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)+(0.0763P)²+0.0414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                1826
_reflns_number_total             1972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02533_si_007.cif
_cod_data_source_block           sfy23
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555348
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.41805(15) 0.4077(3) 0.41404(12) 0.0490(3) Uani 1 1 d .
O2 O 0.0571(2) -0.0216(3) 0.31820(19) 0.0646(5) Uani 1 1 d .
O3 O 0.80656(15) -0.0003(3) -0.00048(12) 0.0490(3) Uani 1 1 d .
N1 N 0.19888(14) 0.2871(2) 0.30002(11) 0.0327(2) Uani 1 1 d .
C1 C 0.35874(18) 0.2227(3) 0.35154(14) 0.0363(3) Uani 1 1 d .
H1 H 0.3462 0.1088 0.4106 0.044 Uiso 1 1 calc R
C2 C 0.2806(2) 0.5334(3) 0.44114(17) 0.0448(4) Uani 1 1 d .
H2A H 0.3113 0.6791 0.4536 0.054 Uiso 1 1 calc R
H2B H 0.2296 0.4822 0.5134 0.054 Uiso 1 1 calc R
C3 C 0.16855(19) 0.5074(3) 0.32700(15) 0.0359(3) Uani 1 1 d .
H3 H 0.2008 0.5992 0.2605 0.043 Uiso 1 1 calc R
C4 C -0.01177(19) 0.5114(3) 0.34010(16) 0.0410(3) Uani 1 1 d .
H4 H -0.0721 0.6314 0.3548 0.049 Uiso 1 1 calc R
C5 C -0.07280(18) 0.3203(3) 0.32788(15) 0.0399(3) Uani 1 1 d .
H5 H -0.1826 0.2863 0.3276 0.048 Uiso 1 1 calc R
C6 C 0.06149(19) 0.1689(3) 0.31476(15) 0.0383(3) Uani 1 1 d .
C7 C 0.47530(17) 0.1575(3) 0.25789(13) 0.0346(3) Uani 1 1 d .
C8 C 0.51347(19) 0.2944(3) 0.16365(14) 0.0403(3) Uani 1 1 d .
H8 H 0.4647 0.4260 0.1582 0.048 Uiso 1 1 calc R
C9 C 0.6232(2) 0.2355(3) 0.07846(15) 0.0414(4) Uani 1 1 d .
H9 H 0.6471 0.3268 0.0155 0.050 Uiso 1 1 calc R
C10 C 0.69775(18) 0.0399(3) 0.08697(14) 0.0368(3) Uani 1 1 d .
C11 C 0.6591(2) -0.0988(3) 0.17799(15) 0.0396(3) Uani 1 1 d .
H11 H 0.7069 -0.2310 0.1826 0.048 Uiso 1 1 calc R
C12 C 0.54732(19) -0.0385(3) 0.26309(14) 0.0380(3) Uani 1 1 d .
H12 H 0.5209 -0.1319 0.3244 0.046 Uiso 1 1 calc R
C13 C 0.8981(3) -0.1890(4) 0.01068(19) 0.0598(5) Uani 1 1 d .
H13A H 0.9537 -0.1943 0.0900 0.090 Uiso 1 1 calc R
H13B H 0.9762 -0.1930 -0.0515 0.090 Uiso 1 1 calc R
H13C H 0.8264 -0.3073 0.0011 0.090 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0357(5) 0.0623(8) 0.0483(6) -0.0188(6) -0.0041(4) -0.0020(6)
O2 0.0585(8) 0.0301(6) 0.1049(14) -0.0026(7) 0.0000(8) -0.0070(6)
O3 0.0447(6) 0.0579(8) 0.0452(6) -0.0037(6) 0.0108(5) 0.0059(7)
N1 0.0314(5) 0.0299(5) 0.0365(5) -0.0011(5) 0.0008(4) -0.0012(5)
C1 0.0336(6) 0.0416(8) 0.0336(6) 0.0015(6) -0.0001(5) 0.0030(6)
C2 0.0426(8) 0.0456(9) 0.0462(8) -0.0139(7) 0.0036(6) -0.0071(7)
C3 0.0359(6) 0.0283(6) 0.0435(7) 0.0017(6) 0.0029(5) -0.0028(5)
C4 0.0370(7) 0.0349(7) 0.0515(8) 0.0018(7) 0.0046(6) 0.0046(6)
C5 0.0312(6) 0.0410(8) 0.0475(8) 0.0034(7) 0.0025(5) -0.0016(6)
C6 0.0369(7) 0.0324(7) 0.0453(8) -0.0008(6) -0.0009(6) -0.0039(6)
C7 0.0311(6) 0.0379(7) 0.0347(6) 0.0019(6) 0.0001(5) 0.0029(6)
C8 0.0374(7) 0.0402(8) 0.0435(7) 0.0076(7) 0.0031(5) 0.0057(6)
C9 0.0399(7) 0.0445(9) 0.0402(7) 0.0084(6) 0.0039(6) 0.0023(7)
C10 0.0307(6) 0.0430(8) 0.0364(6) -0.0045(6) -0.0002(5) -0.0015(6)
C11 0.0388(7) 0.0362(7) 0.0438(7) -0.0019(6) 0.0021(6) 0.0041(6)
C12 0.0385(7) 0.0366(7) 0.0388(7) 0.0043(6) 0.0023(5) 0.0007(6)
C13 0.0577(10) 0.0693(14) 0.0530(10) -0.0089(10) 0.0096(8) 0.0180(11)
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
C2 O1 C1 107.73(12)
C10 O3 C13 117.54(16)
C6 N1 C3 110.65(13)
C6 N1 C1 122.03(14)
C3 N1 C1 110.62(13)
O1 C1 N1 103.32(13)
O1 C1 C7 109.78(13)
N1 C1 C7 114.21(12)
O1 C2 C3 102.86(13)
N1 C3 C4 102.49(13)
N1 C3 C2 99.62(13)
C4 C3 C2 118.79(14)
C5 C4 C3 110.39(14)
C4 C5 C6 109.13(14)
O2 C6 N1 125.23(18)
O2 C6 C5 128.62(18)
N1 C6 C5 106.14(14)
C12 C7 C8 118.77(14)
C12 C7 C1 120.72(14)
C8 C7 C1 120.50(14)
C9 C8 C7 120.48(16)
C8 C9 C10 119.98(16)
O3 C10 C11 124.62(16)
O3 C10 C9 115.10(15)
C11 C10 C9 120.28(15)
C10 C11 C12 119.29(16)
C7 C12 C11 121.15(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.430(2)
O1 C1 1.435(2)
O2 C6 1.214(2)
O3 C10 1.3677(19)
O3 C13 1.421(3)
N1 C6 1.376(2)
N1 C3 1.458(2)
N1 C1 1.4639(19)
C1 C7 1.498(2)
C2 C3 1.523(2)
C3 C4 1.500(2)
C4 C5 1.321(2)
C5 C6 1.480(2)
C7 C12 1.382(2)
C7 C8 1.398(2)
C8 C9 1.382(2)
C9 C10 1.390(2)
C10 C11 1.380(2)
C11 C12 1.396(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O2 0.93 2.49 3.039(2) 117.7 1_565
