#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/53/1555344.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_1555344
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            'C11 H19 N O2'
_chemical_formula_weight         197.27
_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            8
_cell_length_a                   10.7069(7)
_cell_length_b                   10.8672(6)
_cell_length_c                   19.6560(12)
_cell_measurement_reflns_used    7669
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.10
_cell_measurement_theta_min      4.50
_cell_volume                     2287.1(2)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14437
_diffrn_reflns_theta_full        69.55
_diffrn_reflns_theta_max         69.55
_diffrn_reflns_theta_min         4.50
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0473
_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)+(0.1000P)²+0.3878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                3810
_reflns_number_total             4026
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02533_si_004.cif
_cod_data_source_block           z333
_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               1555344
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
O1 O 0.38855(11) 0.15849(11) 0.02125(7) 0.0404(3) Uani 1 1 d .
O3 O 0.36711(11) 0.85506(11) 0.01186(7) 0.0384(3) Uani 1 1 d .
O4 O 0.68123(13) 1.05641(11) 0.06554(7) 0.0410(3) Uani 1 1 d .
N1 N 0.18255(14) 0.10260(12) 0.02819(8) 0.0333(3) Uani 1 1 d .
O2 O 0.08282(13) -0.05539(11) 0.08135(7) 0.0427(3) Uani 1 1 d .
N2 N 0.57638(14) 0.89761(12) 0.01593(8) 0.0324(3) Uani 1 1 d .
C12 C 0.46683(16) 0.86980(14) -0.01581(9) 0.0325(4) Uani 1 1 d .
C7 C 0.17706(18) 0.03510(16) 0.09232(9) 0.0355(4) Uani 1 1 d .
H7 H 0.2573 -0.0057 0.1005 0.043 Uiso 1 1 calc R
C18 C 0.58576(18) 0.96797(15) 0.07922(9) 0.0338(4) Uani 1 1 d .
H18 H 0.5066 1.0107 0.0877 0.041 Uiso 1 1 calc R
C1 C 0.28869(16) 0.13661(13) -0.00516(9) 0.0333(4) Uani 1 1 d .
C19 C 0.62251(18) 0.89448(16) 0.14243(9) 0.0364(4) Uani 1 1 d .
C17 C 0.69871(19) 1.06538(16) -0.00640(10) 0.0410(4) Uani 1 1 d .
H17A H 0.7829 1.0920 -0.0173 0.049 Uiso 1 1 calc R
H17B H 0.6396 1.1225 -0.0264 0.049 Uiso 1 1 calc R
C4 C 0.08328(18) 0.06018(16) -0.01759(10) 0.0387(4) Uani 1 1 d .
H4 H 0.0085 0.1117 -0.0140 0.046 Uiso 1 1 calc R
C15 C 0.67548(18) 0.93531(16) -0.03111(10) 0.0377(4) Uani 1 1 d .
H15 H 0.7501 0.8839 -0.0259 0.045 Uiso 1 1 calc R
C13 C 0.49438(17) 0.85829(16) -0.09150(9) 0.0364(4) Uani 1 1 d .
H13A H 0.4999 0.7724 -0.1046 0.044 Uiso 1 1 calc R
H13B H 0.4289 0.8971 -0.1180 0.044 Uiso 1 1 calc R
C2 C 0.25785(18) 0.14423(15) -0.08031(9) 0.0382(4) Uani 1 1 d .
H2A H 0.3263 0.1125 -0.1075 0.046 Uiso 1 1 calc R
H2B H 0.2420 0.2288 -0.0936 0.046 Uiso 1 1 calc R
C3 C 0.1416(2) 0.0661(2) -0.09004(11) 0.0487(5) Uani 1 1 d .
H3 H 0.1672 -0.0170 -0.1034 0.058 Uiso 1 1 calc R
C6 C 0.06077(19) -0.06707(17) 0.00994(11) 0.0435(5) Uani 1 1 d .
H6A H -0.0243 -0.0934 0.0011 0.052 Uiso 1 1 calc R
H6B H 0.1179 -0.1259 -0.0103 0.052 Uiso 1 1 calc R
C8 C 0.1412(2) 0.11193(18) 0.15490(10) 0.0440(5) Uani 1 1 d .
C14 C 0.6185(2) 0.92268(18) -0.10335(10) 0.0436(4) Uani 1 1 d .
H14 H 0.6027 1.0050 -0.1218 0.052 Uiso 1 1 calc R
C22 C 0.74603(19) 0.82724(18) 0.13088(10) 0.0428(4) Uani 1 1 d .
H22A H 0.7657 0.7787 0.1702 0.064 Uiso 1 1 calc R
H22B H 0.8113 0.8863 0.1233 0.064 Uiso 1 1 calc R
H22C H 0.7387 0.7745 0.0919 0.064 Uiso 1 1 calc R
C21 C 0.6354(2) 0.98471(18) 0.20177(11) 0.0474(5) Uani 1 1 d .
H21A H 0.5575 1.0265 0.2087 0.071 Uiso 1 1 calc R
H21B H 0.6994 1.0438 0.1915 0.071 Uiso 1 1 calc R
H21C H 0.6576 0.9404 0.2423 0.071 Uiso 1 1 calc R
C9 C 0.2447(2) 0.2066(2) 0.16699(12) 0.0552(6) Uani 1 1 d .
H9A H 0.2516 0.2594 0.1280 0.083 Uiso 1 1 calc R
H9B H 0.3226 0.1648 0.1742 0.083 Uiso 1 1 calc R
H9C H 0.2248 0.2550 0.2064 0.083 Uiso 1 1 calc R
C20 C 0.5190(2) 0.80198(18) 0.15772(10) 0.0455(5) Uani 1 1 d .
H20A H 0.4412 0.8448 0.1632 0.068 Uiso 1 1 calc R
H20B H 0.5385 0.7583 0.1988 0.068 Uiso 1 1 calc R
H20C H 0.5122 0.7447 0.1207 0.068 Uiso 1 1 calc R
C11 C 0.0172(2) 0.1767(2) 0.14357(12) 0.0522(5) Uani 1 1 d .
H11A H -0.0034 0.2246 0.1831 0.078 Uiso 1 1 calc R
H11B H -0.0470 0.1166 0.1358 0.078 Uiso 1 1 calc R
H11C H 0.0235 0.2298 0.1047 0.078 Uiso 1 1 calc R
C10 C 0.1335(3) 0.0243(2) 0.21600(12) 0.0642(7) Uani 1 1 d .
H10A H 0.1161 0.0706 0.2565 0.096 Uiso 1 1 calc R
H10B H 0.2116 -0.0181 0.2212 0.096 Uiso 1 1 calc R
H10C H 0.0680 -0.0345 0.2086 0.096 Uiso 1 1 calc R
C16 C 0.7046(2) 0.8531(3) -0.15183(11) 0.0601(6) Uani 1 1 d .
H16A H 0.7212 0.7726 -0.1338 0.090 Uiso 1 1 calc R
H16B H 0.7817 0.8973 -0.1567 0.090 Uiso 1 1 calc R
H16C H 0.6651 0.8456 -0.1955 0.090 Uiso 1 1 calc R
C5 C 0.0509(3) 0.1145(3) -0.14230(13) 0.0775(8) Uani 1 1 d .
H5A H 0.0292 0.1979 -0.1314 0.116 Uiso 1 1 calc R
H5B H -0.0230 0.0646 -0.1423 0.116 Uiso 1 1 calc R
H5C H 0.0889 0.1119 -0.1865 0.116 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 0.0181 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
C18 O4 C17 109.01(13)
C1 N1 C7 125.81(14)
C1 N1 C4 113.22(15)
C7 N1 C4 110.04(14)
C7 O2 C6 109.08(13)
C12 N2 C18 124.34(15)
C12 N2 C15 113.36(14)
C18 N2 C15 109.90(13)
O3 C12 N2 125.71(16)
O3 C12 C13 126.88(16)
N2 C12 C13 107.39(15)
O2 C7 N1 104.15(13)
O2 C7 C8 108.64(15)
N1 C7 C8 115.38(14)
O4 C18 N2 103.92(14)
O4 C18 C19 108.68(15)
N2 C18 C19 115.83(13)
O1 C1 N1 125.64(16)
O1 C1 C2 126.78(17)
N1 C1 C2 107.57(15)
C20 C19 C22 110.06(15)
C20 C19 C18 108.49(16)
C22 C19 C18 110.61(16)
C20 C19 C21 109.74(16)
C22 C19 C21 109.96(16)
C18 C19 C21 107.95(14)
O4 C17 C15 103.41(14)
N1 C4 C6 100.63(15)
N1 C4 C3 104.94(15)
C6 C4 C3 115.57(16)
N2 C15 C17 100.22(15)
N2 C15 C14 105.54(15)
C17 C15 C14 116.13(16)
C14 C13 C12 106.35(15)
C1 C2 C3 105.71(15)
C5 C3 C2 114.7(2)
C5 C3 C4 112.3(2)
C2 C3 C4 103.69(16)
O2 C6 C4 104.19(14)
C11 C8 C9 110.14(17)
C11 C8 C10 110.78(18)
C9 C8 C10 109.55(19)
C11 C8 C7 110.65(17)
C9 C8 C7 108.01(17)
C10 C8 C7 107.63(16)
C13 C14 C16 113.31(17)
C13 C14 C15 104.13(15)
C16 C14 C15 112.18(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.212(2)
O3 C12 1.209(2)
O4 C18 1.429(2)
O4 C17 1.430(2)
N1 C1 1.363(2)
N1 C7 1.460(2)
N1 C4 1.467(2)
O2 C7 1.425(2)
O2 C6 1.429(3)
N2 C12 1.362(2)
N2 C18 1.464(2)
N2 C15 1.466(2)
C12 C13 1.522(2)
C7 C8 1.535(3)
C18 C19 1.528(2)
C1 C2 1.516(3)
C19 C20 1.526(3)
C19 C22 1.528(3)
C19 C21 1.530(2)
C17 C15 1.515(3)
C4 C6 1.504(3)
C4 C3 1.556(3)
C15 C14 1.552(3)
C13 C14 1.520(3)
C2 C3 1.519(3)
C3 C5 1.508(3)
C8 C11 1.520(3)
C8 C9 1.530(3)
C8 C10 1.535(3)
C14 C16 1.527(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305122
