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#$Date: 2022-02-03 04:07:43 +0200 (Thu, 03 Feb 2022) $
#$Revision: 272442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/43/7244334.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_7244334
loop_
_publ_author_name
'Reyes-Bravo, Enrique'
'Gnecco, Dino'
'Juárez, Jorge R.'
'Orea, María L.'
'Bernès, Sylvain'
'Aparicio, David M.'
'Terán, Joel L.'
_publ_section_title
;
 Diastereoselective synthesis of new zwitterionic bicyclic lactams,
 scaffolds for construction of 2-substituted-4-hydroxy piperidine and its
 pipecolic acid derivatives
;
_journal_issue                   7
_journal_name_full               'RSC Advances'
_journal_page_first              4187
_journal_page_last               4190
_journal_paper_doi               10.1039/D1RA09298G
_journal_volume                  12
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-06-25
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-30 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4810(4)
_cell_length_b                   10.4640(9)
_cell_length_c                   15.9980(10)
_cell_measurement_reflns_used    18729
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      24.84
_cell_measurement_theta_min      2.37
_cell_volume                     1252.34(15)
_computing_cell_refinement       'X-AREA 1.82'
_computing_data_collection       'X-AREA 1.82 (Stoe & Cie, 2018)'
_computing_data_reduction        'X-AREA 1.82'
_computing_molecular_graphics
'XP in SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'PublCif (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295(1)
_diffrn_detector                 'Reverse-biased silicon diode array'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'Dectris Pilatus 100K R'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
1400 frames, 20 s/frame, 1 deg./frame, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian four-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  -90
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56083
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            40682
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        19.664
_diffrn_reflns_theta_max         22.494
_diffrn_reflns_theta_min         2.372
_diffrn_source                   'Sealed X-ray tube'
_diffrn_source_current           0.600
_diffrn_source_power             0.039
_diffrn_source_type              'Axo Astix-f Microfocus source'
_diffrn_source_voltage           65
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'X-AREA 1.82 (Stoe & Cie, 2018)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.020(4)
_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   0.813
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.813
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0379
_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)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1955
_reflns_number_total             3318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra09298g2.cif
_cod_data_source_block           29
_cod_database_code               7244334
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_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_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 0.08851(17) 0.57286(15) 0.25693(10) 0.0574(4) Uani 1 1 d . . . . .
C2 C 0.2499(3) 0.5008(2) 0.24310(16) 0.0553(6) Uani 1 1 d . . . . .
H2A H 0.264449 0.480864 0.184277 0.066 Uiso 1 1 calc R U . . .
H2B H 0.248204 0.421696 0.274710 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4003(3) 0.5889(2) 0.27367(13) 0.0465(5) Uani 1 1 d . . . . .
H3A H 0.492397 0.538326 0.302012 0.056 Uiso 1 1 calc R U . . .
N4 N 0.30251(19) 0.66624(18) 0.33505(11) 0.0438(4) Uani 1 1 d . . . . .
C5 C 0.3777(3) 0.7541(2) 0.38439(12) 0.0470(5) Uani 1 1 d . . . . .
O2 O 0.53935(19) 0.77441(18) 0.38523(10) 0.0644(5) Uani 1 1 d . . . . .
C6 C 0.2502(3) 0.8283(2) 0.43897(14) 0.0524(6) Uani 1 1 d . . . . .
H6A H 0.299513 0.913040 0.447343 0.063 Uiso 1 1 calc R U . . .
H6B H 0.245819 0.786941 0.493204 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0610(3) 0.8428(2) 0.40766(14) 0.0496(5) Uani 1 1 d . . . . .
O3 O -0.0367(2) 0.92196(18) 0.43823(11) 0.0730(5) Uani 1 1 d . . . . .
C8 C 0.0028(2) 0.7566(2) 0.33744(15) 0.0522(6) Uani 1 1 d . . . . .
H8A H 0.017167 0.801141 0.284679 0.063 Uiso 1 1 calc R U . . .
H8B H -0.122934 0.736369 0.344085 0.063 Uiso 1 1 calc R U . . .
C8A C 0.1096(2) 0.6341(2) 0.33538(14) 0.0480(5) Uani 1 1 d . . . . .
C9 C 0.4837(2) 0.6654(2) 0.20363(13) 0.0453(5) Uani 1 1 d . . . . .
C10 C 0.3881(3) 0.7582(2) 0.16074(15) 0.0591(6) Uani 1 1 d . . . . .
H10A H 0.273985 0.780545 0.178650 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4611(4) 0.8178(3) 0.09171(16) 0.0711(7) Uani 1 1 d . . . . .
H11A H 0.396295 0.880390 0.063724 0.085 Uiso 1 1 calc R U . . .
C12 C 0.6278(4) 0.7853(3) 0.06427(16) 0.0767(8) Uani 1 1 d . . . . .
H12A H 0.675139 0.823484 0.016684 0.092 Uiso 1 1 calc R U . . .
C13 C 0.7250(4) 0.6958(3) 0.10741(18) 0.0746(8) Uani 1 1 d . . . . .
H13A H 0.839684 0.674878 0.089604 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6541(3) 0.6365(2) 0.17709(15) 0.0574(6) Uani 1 1 d . . . . .
H14A H 0.721793 0.576709 0.206218 0.069 Uiso 1 1 calc R U . . .
C15 C 0.0610(3) 0.5451(2) 0.40656(17) 0.0679(7) Uani 1 1 d . . . . .
H15A H 0.128881 0.467565 0.401829 0.102 Uiso 1 1 calc R U . . .
H15B H -0.064242 0.525618 0.404053 0.102 Uiso 1 1 calc R U . . .
H15C H 0.087696 0.585740 0.458898 0.102 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 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 '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
C8A O1 C2 106.21(15) . . ?
O1 C2 C3 104.54(17) . . ?
N4 C3 C9 114.19(18) . . ?
N4 C3 C2 100.31(15) . . ?
C9 C3 C2 112.60(18) . . ?
C5 N4 C3 124.39(16) . . ?
C5 N4 C8A 124.35(17) . . ?
C3 N4 C8A 111.26(17) . . ?
O2 C5 N4 122.7(2) . . ?
O2 C5 C6 121.8(2) . . ?
N4 C5 C6 115.46(16) . . ?
C5 C6 C7 116.94(19) . . ?
O3 C7 C8 122.6(2) . . ?
O3 C7 C6 120.2(2) . . ?
C8 C7 C6 117.29(19) . . ?
C7 C8 C8A 111.82(17) . . ?
O1 C8A N4 102.00(15) . . ?
O1 C8A C8 110.11(18) . . ?
N4 C8A C8 108.82(17) . . ?
O1 C8A C15 111.14(18) . . ?
N4 C8A C15 112.08(19) . . ?
C8 C8A C15 112.22(18) . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 C3 119.6(2) . . ?
C10 C9 C3 121.62(18) . . ?
C11 C10 C9 120.5(2) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 119.5(3) . . ?
C12 C13 C14 120.6(2) . . ?
C9 C14 C13 120.4(3) . . ?
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 C8A 1.418(3) . ?
O1 C2 1.440(3) . ?
C2 C3 1.535(3) . ?
C3 N4 1.468(3) . ?
C3 C9 1.512(3) . ?
N4 C5 1.336(3) . ?
N4 C8A 1.482(2) . ?
C5 O2 1.228(2) . ?
C5 C6 1.508(3) . ?
C6 C7 1.509(3) . ?
C7 O3 1.208(3) . ?
C7 C8 1.505(3) . ?
C8 C8A 1.511(3) . ?
C8A C15 1.515(3) . ?
C9 C14 1.377(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.381(3) . ?
C11 C12 1.365(4) . ?
C12 C13 1.372(4) . ?
C13 C14 1.382(4) . ?
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
_geom_hbond_publ_flag
C6 H6B O2 0.97 2.57 3.399(3) 144.1 4_466 yes
C8 H8B O2 0.97 2.64 3.555(2) 157.2 1_455 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A O1 C2 C3 -40.6(2) . . . . ?
O1 C2 C3 N4 26.3(2) . . . . ?
O1 C2 C3 C9 -95.5(2) . . . . ?
C9 C3 N4 C5 -63.9(3) . . . . ?
C2 C3 N4 C5 175.5(2) . . . . ?
C9 C3 N4 C8A 116.26(19) . . . . ?
C2 C3 N4 C8A -4.4(2) . . . . ?
C3 N4 C5 O2 -3.2(4) . . . . ?
C8A N4 C5 O2 176.6(2) . . . . ?
C3 N4 C5 C6 176.26(19) . . . . ?
C8A N4 C5 C6 -3.9(3) . . . . ?
O2 C5 C6 C7 152.4(2) . . . . ?
N4 C5 C6 C7 -27.2(3) . . . . ?
C5 C6 C7 O3 -164.3(2) . . . . ?
C5 C6 C7 C8 15.0(3) . . . . ?
O3 C7 C8 C8A -155.2(2) . . . . ?
C6 C7 C8 C8A 25.5(3) . . . . ?
C2 O1 C8A N4 36.4(2) . . . . ?
C2 O1 C8A C8 151.81(17) . . . . ?
C2 O1 C8A C15 -83.2(2) . . . . ?
C5 N4 C8A O1 160.98(19) . . . . ?
C3 N4 C8A O1 -19.1(2) . . . . ?
C5 N4 C8A C8 44.6(3) . . . . ?
C3 N4 C8A C8 -135.48(18) . . . . ?
C5 N4 C8A C15 -80.1(3) . . . . ?
C3 N4 C8A C15 99.8(2) . . . . ?
C7 C8 C8A O1 -163.52(17) . . . . ?
C7 C8 C8A N4 -52.5(2) . . . . ?
C7 C8 C8A C15 72.1(2) . . . . ?
N4 C3 C9 C14 137.7(2) . . . . ?
C2 C3 C9 C14 -108.8(2) . . . . ?
N4 C3 C9 C10 -47.3(3) . . . . ?
C2 C3 C9 C10 66.3(3) . . . . ?
C14 C9 C10 C11 1.6(3) . . . . ?
C3 C9 C10 C11 -173.5(2) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C13 -2.1(4) . . . . ?
C11 C12 C13 C14 1.5(4) . . . . ?
C10 C9 C14 C13 -2.3(3) . . . . ?
C3 C9 C14 C13 172.9(2) . . . . ?
C12 C13 C14 C9 0.8(4) . . . . ?
