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#$Date: 2023-06-05 07:56:45 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284327 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/92/7159290.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_7159290
loop_
_publ_author_name
'Singh, Manjeet'
'Kumar, Manish'
'Nalawade, Sachin A.'
'Puneeth Kumar, DRGKoppalu R'
'Gopi, Hosahudya N.'
_publ_section_title
;
 Cyclization of N-Boc-(E)-α,β-unsaturated
 γ-amino acid active esters into
 N-Boc-(Z)-α,β-unsaturated γ-lactams
 through E → Z isomerization.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3766
_journal_page_last               3769
_journal_paper_doi               10.1039/d3ob00127j
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-12-12 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.499(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.146(3)
_cell_length_b                   14.129(7)
_cell_length_c                   16.674(8)
_cell_measurement_reflns_used    3576
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.476
_cell_measurement_theta_min      1.900
_cell_volume                     1428.1(12)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1952
_diffrn_reflns_av_unetI/netI     0.1905
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20509
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.476
_diffrn_reflns_theta_min         1.900
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       plate
_exptl_crystal_F_000             584.0
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.048(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.790
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.790
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0723
_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)+(0.1585P)²+1.7248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.2710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1499
_reflns_number_total             3576
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00127j2.cif
_cod_data_source_block           Monc1_a
_cod_depositor_comments
'Adding full bibliography for 7159285--7159290.cif.'
_cod_original_cell_volume        1427.9(12)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        C16H19NO3
_cod_database_code               7159290
_shelx_shelxl_version_number     2018/3
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4987(4) 0.67066(18) 0.72517(15) 0.0255(7) Uani 1 1 d . . . . .
O3 O 0.0563(5) 0.86609(19) 0.59855(17) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.1334(5) 0.7112(2) 0.70536(17) 0.0311(7) Uani 1 1 d . . . . .
N1 N 0.3786(5) 0.7744(2) 0.62887(19) 0.0251(8) Uani 1 1 d . . . . .
C5 C 0.3176(7) 0.7174(3) 0.6898(2) 0.0251(9) Uani 1 1 d . . . . .
C7 C 0.3758(7) 0.8918(3) 0.5344(2) 0.0262(9) Uani 1 1 d . . . . .
H7 H 0.328379 0.942024 0.499898 0.031 Uiso 1 1 calc R U . . .
C8 C 0.5733(7) 0.8520(3) 0.5415(2) 0.0271(9) Uani 1 1 d . . . . .
H8 H 0.684271 0.871583 0.513478 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2424(7) 0.8460(3) 0.5883(2) 0.0269(9) Uani 1 1 d . . . . .
C9 C 0.5942(7) 0.7709(3) 0.6008(2) 0.0259(9) Uani 1 1 d . . . . .
H9 H 0.712879 0.783814 0.646385 0.031 Uiso 1 1 calc R U . . .
C14 C 0.1422(7) 0.6293(3) 0.3500(3) 0.0294(10) Uani 1 1 d . . . . .
H14 H 0.031985 0.622117 0.304966 0.035 Uiso 1 1 calc R U . . .
C3 C 0.4786(7) 0.5888(3) 0.7800(2) 0.0259(9) Uani 1 1 d . . . . .
C11 C 0.4686(7) 0.6552(3) 0.4860(2) 0.0251(9) Uani 1 1 d . . . . .
C2 C 0.7173(7) 0.5557(3) 0.8002(2) 0.0289(10) Uani 1 1 d . . . . .
H2A H 0.769272 0.538432 0.750978 0.043 Uiso 1 1 calc R U . . .
H2B H 0.726084 0.501852 0.835717 0.043 Uiso 1 1 calc R U . . .
H2C H 0.806964 0.605938 0.826621 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5034(7) 0.6832(3) 0.4092(2) 0.0286(10) Uani 1 1 d . . . . .
H16 H 0.637329 0.710697 0.403259 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6389(7) 0.6766(3) 0.5599(2) 0.0265(9) Uani 1 1 d . . . . .
H10A H 0.783600 0.679262 0.543950 0.032 Uiso 1 1 calc R U . . .
H10B H 0.640249 0.625668 0.598978 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2692(7) 0.6114(3) 0.4935(3) 0.0293(10) Uani 1 1 d . . . . .
H12 H 0.244856 0.590598 0.544186 0.035 Uiso 1 1 calc R U . . .
C4 C 0.3347(7) 0.5135(3) 0.7329(3) 0.0308(10) Uani 1 1 d . . . . .
H4A H 0.186581 0.536793 0.718870 0.046 Uiso 1 1 calc R U . . .
H4B H 0.335081 0.457680 0.765737 0.046 Uiso 1 1 calc R U . . .
H4C H 0.391441 0.498310 0.684107 0.046 Uiso 1 1 calc R U . . .
C15 C 0.3413(7) 0.6709(3) 0.3410(2) 0.0304(10) Uani 1 1 d . . . . .
H15 H 0.366312 0.690326 0.290022 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1066(7) 0.5985(3) 0.4257(3) 0.0295(10) Uani 1 1 d . . . . .
H13 H -0.025741 0.569306 0.431165 0.035 Uiso 1 1 calc R U . . .
C1 C 0.3945(7) 0.6208(3) 0.8564(2) 0.0296(10) Uani 1 1 d . . . . .
H1A H 0.482503 0.672672 0.880605 0.044 Uiso 1 1 calc R U . . .
H1B H 0.404198 0.569197 0.894322 0.044 Uiso 1 1 calc R U . . .
H1C H 0.243547 0.640605 0.842506 0.044 Uiso 1 1 calc R U . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C3 120.2(3) . . ?
C5 N1 C6 123.6(4) . . ?
C5 N1 C9 125.0(3) . . ?
C6 N1 C9 111.4(3) . . ?
O2 C5 O1 127.6(4) . . ?
O2 C5 N1 124.9(4) . . ?
O1 C5 N1 107.5(4) . . ?
C8 C7 C6 110.8(4) . . ?
C8 C7 H7 124.6 . . ?
C6 C7 H7 124.6 . . ?
C7 C8 C9 111.0(4) . . ?
C7 C8 H8 124.5 . . ?
C9 C8 H8 124.5 . . ?
O3 C6 N1 126.6(4) . . ?
O3 C6 C7 128.1(4) . . ?
N1 C6 C7 105.3(3) . . ?
N1 C9 C8 101.5(3) . . ?
N1 C9 C10 113.9(3) . . ?
C8 C9 C10 111.7(3) . . ?
N1 C9 H9 109.9 . . ?
C8 C9 H9 109.9 . . ?
C10 C9 H9 109.9 . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
O1 C3 C4 109.0(3) . . ?
O1 C3 C1 110.9(3) . . ?
C4 C3 C1 113.1(4) . . ?
O1 C3 C2 101.5(3) . . ?
C4 C3 C2 110.9(3) . . ?
C1 C3 C2 110.8(3) . . ?
C16 C11 C12 118.6(4) . . ?
C16 C11 C10 120.2(4) . . ?
C12 C11 C10 121.1(4) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C11 C16 C15 121.2(4) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C15 C14 119.3(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.343(4) . ?
O1 C3 1.493(5) . ?
O3 C6 1.218(5) . ?
O2 C5 1.206(5) . ?
N1 C5 1.396(5) . ?
N1 C6 1.412(5) . ?
N1 C9 1.477(5) . ?
C7 C8 1.325(6) . ?
C7 C6 1.463(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.505(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.541(5) . ?
C9 H9 0.9800 . ?
C14 C13 1.386(6) . ?
C14 C15 1.387(6) . ?
C14 H14 0.9300 . ?
C3 C4 1.518(5) . ?
C3 C1 1.520(6) . ?
C3 C2 1.524(6) . ?
C11 C16 1.390(6) . ?
C11 C12 1.397(6) . ?
C11 C10 1.510(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C16 C15 1.394(5) . ?
C16 H16 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.391(6) . ?
C12 H12 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
