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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/53/1555346.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_1555346
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            'C9 H15 N O2'
_chemical_formula_weight         169.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.426(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1254(3)
_cell_length_b                   6.9441(4)
_cell_length_c                   10.8047(6)
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      69.79
_cell_measurement_theta_min      4.19
_cell_volume                     448.82(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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5783
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.618
_diffrn_reflns_theta_min         4.190
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             184
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details
; 
 Flack x determined using 670 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(16)
_refine_ls_extinction_coef       0.051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0767P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                1604
_reflns_number_total             1643
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b02533_si_005.cif
_cod_data_source_block           Z594_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1555346
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.6208(3) 1.0263(2) 0.20891(13) 0.0174(4) Uani 1 1 d . .
O1 O 0.5135(2) 0.9598(2) 0.39150(12) 0.0222(4) Uani 1 1 d . .
O2 O 0.7814(2) 1.2551(2) 0.10220(13) 0.0262(4) Uani 1 1 d . .
C1 C 0.5911(3) 0.8186(3) 0.21168(16) 0.0187(5) Uani 1 1 d . .
H1 H 0.4369 0.7837 0.1651 0.022 Uiso 1 1 calc R U
C2 C 0.6122(4) 0.7874(3) 0.35326(19) 0.0233(5) Uani 1 1 d . .
H2A H 0.5293 0.6712 0.3699 0.028 Uiso 1 1 calc R U
H2B H 0.7706 0.7749 0.3977 0.028 Uiso 1 1 calc R U
C3 C 0.5777(3) 1.1201(3) 0.32302(16) 0.0181(5) Uani 1 1 d . .
C7 C 0.7724(3) 0.9092(3) 0.04691(18) 0.0222(5) Uani 1 1 d . .
H7A H 0.9200 0.9157 0.0237 0.027 Uiso 1 1 calc R U
H7B H 0.6550 0.8947 -0.0313 0.027 Uiso 1 1 calc R U
C9 C 0.9948(3) 0.7033(3) 0.2217(2) 0.0247(5) Uani 1 1 d . .
H9A H 1.0520 0.8214 0.2669 0.037 Uiso 1 1 calc R U
H9B H 1.0968 0.6620 0.1683 0.037 Uiso 1 1 calc R U
H9C H 0.9840 0.6019 0.2832 0.037 Uiso 1 1 calc R U
C4 C 0.7892(4) 1.2136(3) 0.39943(19) 0.0252(5) Uani 1 1 d . .
H4A H 0.7565 1.2740 0.4754 0.038 Uiso 1 1 calc R U
H4B H 0.8420 1.3117 0.3476 0.038 Uiso 1 1 calc R U
H4C H 0.9050 1.1153 0.4245 0.038 Uiso 1 1 calc R U
C5 C 0.3832(3) 1.2587(3) 0.29371(17) 0.0245(5) Uani 1 1 d . .
H5A H 0.2542 1.1944 0.2403 0.037 Uiso 1 1 calc R U
H5B H 0.4248 1.3709 0.2488 0.037 Uiso 1 1 calc R U
H5C H 0.3447 1.3005 0.3729 0.037 Uiso 1 1 calc R U
C8 C 0.7644(3) 0.7414(3) 0.13900(18) 0.0200(5) Uani 1 1 d . .
H8 H 0.7061 0.6226 0.0907 0.024 Uiso 1 1 calc R U
C6 C 0.7313(3) 1.0883(3) 0.12031(17) 0.0174(4) Uani 1 1 d . .
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
C6 N1 C1 114.38(14)
C6 N1 C3 131.26(17)
C1 N1 C3 112.14(14)
C2 O1 C3 108.50(12)
N1 C1 C2 100.23(14)
N1 C1 C8 103.34(14)
C2 C1 C8 122.85(16)
O1 C2 C1 102.71(16)
O1 C3 N1 101.97(14)
O1 C3 C5 108.06(15)
N1 C3 C5 112.50(14)
O1 C3 C4 110.25(15)
N1 C3 C4 111.04(15)
C5 C3 C4 112.47(17)
C6 C7 C8 104.43(14)
C9 C8 C7 110.88(15)
C9 C8 C1 114.41(15)
C7 C8 C1 100.79(15)
O2 C6 N1 126.40(18)
O2 C6 C7 127.82(18)
N1 C6 C7 105.75(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.356(2)
N1 C1 1.455(3)
N1 C3 1.468(2)
O1 C2 1.441(2)
O1 C3 1.438(2)
O2 C6 1.224(3)
C1 C2 1.523(3)
C1 C8 1.545(2)
C3 C5 1.511(3)
C3 C4 1.523(3)
C7 C6 1.525(3)
C7 C8 1.540(3)
C9 C8 1.523(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118414533
