#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/53/1555347.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_1555347
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 ad
_chemical_formula_sum            'C8 H11 N O2'
_chemical_formula_weight         153.18
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7420(2)
_cell_length_b                   7.2944(2)
_cell_length_c                   15.8577(4)
_cell_measurement_reflns_used    9019
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      5.58
_cell_volume                     779.86(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9616
_diffrn_reflns_theta_full        68.54
_diffrn_reflns_theta_max         68.54
_diffrn_reflns_theta_min         5.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.8184
_exptl_absorpt_correction_T_min  0.6939
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.198
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       0.206(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.339
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.339
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0613
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0894P)²+0.0438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                1413
_reflns_number_total             1420
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02533_si_003.cif
_cod_data_source_block           z292
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' 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      P2(1)2(1)2(1)
_cod_database_code               1555347
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
C1 C 0.6970(2) 0.2224(2) 0.10665(9) 0.0208(4) Uani 1 1 d .
C2 C 0.5103(2) 0.1163(2) 0.10188(10) 0.0238(4) Uani 1 1 d .
H2 H 0.5016 -0.0137 0.1017 0.029 Uiso 1 1 calc R
C3 C 0.3564(2) 0.2302(2) 0.09788(10) 0.0251(4) Uani 1 1 d .
H3 H 0.2211 0.1938 0.0971 0.030 Uiso 1 1 calc R
C4 C 0.4284(2) 0.4240(2) 0.09472(10) 0.0224(4) Uani 1 1 d .
H4 H 0.3865 0.4847 0.0411 0.027 Uiso 1 1 calc R
C5 C 0.3976(2) 0.5514(2) 0.16974(11) 0.0271(4) Uani 1 1 d .
H5A H 0.2711 0.6195 0.1649 0.032 Uiso 1 1 calc R
H5B H 0.3991 0.4827 0.2236 0.032 Uiso 1 1 calc R
C6 C 0.7350(2) 0.5642(2) 0.13930(10) 0.0220(4) Uani 1 1 d .
C7 C 0.8536(2) 0.5116(2) 0.21760(10) 0.0272(4) Uani 1 1 d .
H7A H 0.9061 0.6225 0.2444 0.041 Uiso 1 1 calc R
H7B H 0.9638 0.4313 0.2013 0.041 Uiso 1 1 calc R
H7C H 0.7671 0.4470 0.2574 0.041 Uiso 1 1 calc R
C8 C 0.8554(3) 0.6780(2) 0.07771(10) 0.0294(5) Uani 1 1 d .
H8A H 0.7756 0.7030 0.0273 0.044 Uiso 1 1 calc R
H8B H 0.9752 0.6104 0.0616 0.044 Uiso 1 1 calc R
H8C H 0.8930 0.7941 0.1044 0.044 Uiso 1 1 calc R
N1 N 0.6440(2) 0.40321(18) 0.09781(8) 0.0197(4) Uani 1 1 d .
O1 O 0.86573(17) 0.16383(17) 0.11609(8) 0.0280(4) Uani 1 1 d .
O2 O 0.56442(18) 0.67182(16) 0.16337(8) 0.0272(4) Uani 1 1 d .
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
C1 0.0250(8) 0.0187(8) 0.0186(7) -0.0013(5) 0.0007(6) 0.0010(6)
C2 0.0294(9) 0.0194(8) 0.0226(8) -0.0007(5) -0.0014(6) -0.0030(6)
C3 0.0246(8) 0.0273(9) 0.0233(7) -0.0016(6) -0.0015(6) -0.0045(7)
C4 0.0204(8) 0.0221(8) 0.0246(8) 0.0011(6) -0.0022(5) 0.0026(6)
C5 0.0226(8) 0.0237(8) 0.0348(9) -0.0046(7) 0.0020(6) 0.0034(6)
C6 0.0225(8) 0.0170(7) 0.0266(8) -0.0023(5) 0.0015(6) 0.0004(6)
C7 0.0286(8) 0.0254(9) 0.0275(8) -0.0043(6) -0.0031(7) -0.0036(6)
C8 0.0324(9) 0.0210(8) 0.0350(9) 0.0017(6) 0.0032(8) -0.0050(7)
N1 0.0202(7) 0.0182(7) 0.0209(6) -0.0001(5) -0.0003(5) -0.0003(5)
O1 0.0249(6) 0.0224(6) 0.0368(7) -0.0032(5) -0.0005(5) 0.0039(4)
O2 0.0258(7) 0.0181(6) 0.0377(7) -0.0045(5) 0.0030(5) 0.0022(5)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 C1 N1 126.12(16)
O1 C1 C2 127.86(15)
N1 C1 C2 106.02(13)
C3 C2 C1 109.81(14)
C2 C3 C4 109.79(14)
N1 C4 C3 102.91(12)
N1 C4 C5 99.95(13)
C3 C4 C5 120.40(14)
O2 C5 C4 102.24(12)
O2 C6 N1 102.62(12)
O2 C6 C8 107.40(14)
N1 C6 C8 111.71(13)
O2 C6 C7 109.82(13)
N1 C6 C7 112.28(14)
C8 C6 C7 112.43(14)
C1 N1 C4 111.21(13)
C1 N1 C6 127.51(14)
C4 N1 C6 110.17(13)
C5 O2 C6 108.14(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.224(2)
C1 N1 1.373(2)
C1 C2 1.480(2)
C2 C3 1.331(2)
C3 C4 1.496(2)
C4 N1 1.4622(17)
C4 C5 1.524(2)
C5 O2 1.431(2)
C6 O2 1.4438(19)
C6 N1 1.480(2)
C6 C8 1.517(2)
C6 C7 1.526(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118414096
