#------------------------------------------------------------------------------
#$Date: 2023-01-06 09:59:23 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280141 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106412.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_8106412
loop_
_publ_author_name
'Tan, Jun-Jie'
'Liu, Xiao-Yu'
'Zhang, Jie'
'Chen, Xi'
'Li, Yi-Ming'
'Jiao, Bing-Hua'
_publ_section_title
;
 Crystal structure of
 (R)-1-(2,3-dihydro-1H-pyrrolizin-5-yl)-2,3-dihydroxypropan-1-one,
 C10H13NO3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              7
_journal_page_last               8
_journal_paper_doi               10.1515/ncrs-2016-0099
_journal_volume                  232
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 101.116(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8118(5)
_cell_length_b                   4.9299(2)
_cell_length_c                   16.5436(7)
_cell_measurement_reflns_used    6169
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      65
_cell_measurement_theta_min      4.50
_cell_volume                     945.28(7)
_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      170(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega 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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10070
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_coef       0.0130(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         2946
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_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)+(0.0352P)²+0.1662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                2898
_reflns_number_total             2946
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0099_suppl.cif
_cod_data_source_block           cu
_cod_original_sg_symbol_H-M      P21
_cod_database_code               8106412
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.61299(10) 0.9928(3) 0.11529(8) 0.0363(3) Uani 1 1 d . . .
H6 H 0.5536 1.0560 0.0878 0.055 Uiso 1 1 calc R . .
O5 O 0.59988(10) 0.6984(3) -0.03748(7) 0.0399(3) Uani 1 1 d . . .
H5 H 0.6367 0.8158 -0.0562 0.060 Uiso 1 1 calc R . .
O4 O 0.80900(10) 0.8687(3) -0.00537(7) 0.0408(3) Uani 1 1 d . . .
O3 O 0.37342(9) 0.1183(3) 0.30346(8) 0.0349(3) Uani 1 1 d . . .
H3 H 0.3995 -0.0281 0.3219 0.052 Uiso 1 1 calc R . .
O2 O 0.47257(10) 0.6339(2) 0.36607(7) 0.0304(3) Uani 1 1 d . . .
O1 O 0.57102(10) 0.2859(2) 0.47526(7) 0.0292(3) Uani 1 1 d . . .
N15 N 0.98851(11) 0.6759(3) 0.12807(8) 0.0290(3) Uani 1 1 d . . .
N4 N 0.74433(11) -0.0991(3) 0.45470(8) 0.0266(3) Uani 1 1 d . . .
C22 C 0.61006(14) 0.7074(4) 0.10931(11) 0.0335(4) Uani 1 1 d . . .
H22A H 0.5305 0.6467 0.1009 0.040 Uiso 1 1 calc R . .
H22B H 0.6507 0.6303 0.1607 0.040 Uiso 1 1 calc R . .
C21 C 0.66478(13) 0.6034(4) 0.03881(10) 0.0310(4) Uani 1 1 d . . .
H21 H 0.6639 0.4046 0.0390 0.037 Uiso 1 1 calc R . .
C20 C 0.78949(13) 0.7019(4) 0.04525(10) 0.0293(4) Uani 1 1 d . . .
C16 C 0.87513(13) 0.5894(4) 0.10990(10) 0.0289(4) Uani 1 1 d . . .
C14 C 1.05908(13) 0.8670(4) 0.09102(11) 0.0350(4) Uani 1 1 d . . .
H14A H 1.0282 1.0496 0.0896 0.042 Uiso 1 1 calc R . .
H14B H 1.0647 0.8123 0.0356 0.042 Uiso 1 1 calc R . .
C13 C 1.17633(16) 0.8466(6) 0.15000(13) 0.0505(5) Uani 1 1 d . . .
H13A H 1.2367 0.8111 0.1191 0.061 Uiso 1 1 calc R . .
H13B H 1.1937 1.0160 0.1796 0.061 Uiso 1 1 calc R . .
C19 C 1.04638(14) 0.5346(4) 0.19192(11) 0.0348(4) Uani 1 1 d . . .
C18 C 0.97262(15) 0.3489(5) 0.21740(11) 0.0375(4) Uani 1 1 d . . .
H18 H 0.9909 0.2259 0.2606 0.045 Uiso 1 1 calc R . .
C17 C 0.86532(14) 0.3827(4) 0.16557(10) 0.0318(4) Uani 1 1 d . . .
H17 H 0.7988 0.2843 0.1678 0.038 Uiso 1 1 calc R . .
C12 C 1.17049(16) 0.6190(6) 0.20972(15) 0.0563(6) Uani 1 1 d . . .
H12A H 1.2201 0.4700 0.2006 0.068 Uiso 1 1 calc R . .
H12B H 1.1933 0.6811 0.2661 0.068 Uiso 1 1 calc R . .
C11 C 0.45855(14) 0.2603(4) 0.27099(10) 0.0314(4) Uani 1 1 d . . .
H11A H 0.4210 0.3789 0.2271 0.038 Uiso 1 1 calc R . .
H11B H 0.5050 0.1313 0.2474 0.038 Uiso 1 1 calc R . .
C10 C 0.53723(13) 0.4293(3) 0.33602(10) 0.0261(4) Uani 1 1 d . . .
H10 H 0.5957 0.5166 0.3100 0.031 Uiso 1 1 calc R . .
C9 C 0.59878(12) 0.2567(3) 0.40769(9) 0.0236(3) Uani 1 1 d . . .
C5 C 0.68662(12) 0.0693(3) 0.39377(9) 0.0240(3) Uani 1 1 d . . .
C3 C 0.73494(14) -0.1636(4) 0.53988(10) 0.0335(4) Uani 1 1 d . . .
H3A H 0.6661 -0.2688 0.5419 0.040 Uiso 1 1 calc R . .
H3B H 0.7347 -0.0006 0.5727 0.040 Uiso 1 1 calc R . .
C2 C 0.84450(17) -0.3304(5) 0.56835(13) 0.0520(5) Uani 1 1 d . . .
H2A H 0.8290 -0.4811 0.6023 0.062 Uiso 1 1 calc R . .
H2B H 0.9044 -0.2185 0.6004 0.062 Uiso 1 1 calc R . .
C1 C 0.88310(14) -0.4353(4) 0.49058(13) 0.0413(5) Uani 1 1 d . . .
H1A H 0.9663 -0.4268 0.4963 0.050 Uiso 1 1 calc R . .
H1B H 0.8577 -0.6205 0.4783 0.050 Uiso 1 1 calc R . .
C8 C 0.82480(13) -0.2445(4) 0.42592(11) 0.0322(4) Uani 1 1 d . . .
C7 C 0.82227(14) -0.1706(4) 0.34472(11) 0.0365(4) Uani 1 1 d . . .
H7 H 0.8691 -0.2386 0.3102 0.044 Uiso 1 1 calc R . .
C6 C 0.73589(13) 0.0257(4) 0.32457(11) 0.0312(4) Uani 1 1 d . . .
H6A H 0.7149 0.1122 0.2739 0.037 Uiso 1 1 calc R . .
H2 H 0.474(2) 0.594(6) 0.4151(17) 0.051(7) Uiso 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C22 O6 H6 109.5 . .
C21 O5 H5 109.5 . .
C11 O3 H3 109.5 . .
C10 O2 H2 105.4(18) . .
C19 N15 C16 109.71(15) . .
C19 N15 C14 114.77(13) . .
C16 N15 C14 135.36(14) . .
C8 N4 C5 110.13(14) . .
C8 N4 C3 114.35(14) . .
C5 N4 C3 135.45(14) . .
O6 C22 C21 112.34(15) . .
O6 C22 H22A 109.1 . .
C21 C22 H22A 109.1 . .
O6 C22 H22B 109.1 . .
C21 C22 H22B 109.1 . .
H22A C22 H22B 107.9 . .
O5 C21 C22 109.38(14) . .
O5 C21 C20 107.63(13) . .
C22 C21 C20 112.50(14) . .
O5 C21 H21 109.1 . .
C22 C21 H21 109.1 . .
C20 C21 H21 109.1 . .
O4 C20 C16 124.74(15) . .
O4 C20 C21 117.95(15) . .
C16 C20 C21 117.30(14) . .
N15 C16 C17 106.40(14) . .
N15 C16 C20 123.87(16) . .
C17 C16 C20 129.73(15) . .
N15 C14 C13 102.00(15) . .
N15 C14 H14A 111.4 . .
C13 C14 H14A 111.4 . .
N15 C14 H14B 111.4 . .
C13 C14 H14B 111.4 . .
H14A C14 H14B 109.2 . .
C12 C13 C14 108.41(17) . .
C12 C13 H13A 110.0 . .
C14 C13 H13A 110.0 . .
C12 C13 H13B 110.0 . .
C14 C13 H13B 110.0 . .
H13A C13 H13B 108.4 . .
N15 C19 C18 109.21(14) . .
N15 C19 C12 110.02(18) . .
C18 C19 C12 140.69(19) . .
C19 C18 C17 106.51(17) . .
C19 C18 H18 126.7 . .
C17 C18 H18 126.7 . .
C16 C17 C18 108.17(16) . .
C16 C17 H17 125.9 . .
C18 C17 H17 125.9 . .
C19 C12 C13 104.19(16) . .
C19 C12 H12A 110.9 . .
C13 C12 H12A 110.9 . .
C19 C12 H12B 110.9 . .
C13 C12 H12B 110.9 . .
H12A C12 H12B 108.9 . .
O3 C11 C10 112.56(13) . .
O3 C11 H11A 109.1 . .
C10 C11 H11A 109.1 . .
O3 C11 H11B 109.1 . .
C10 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
O2 C10 C9 109.50(13) . .
O2 C10 C11 109.93(13) . .
C9 C10 C11 112.18(13) . .
O2 C10 H10 108.4 . .
C9 C10 H10 108.4 . .
C11 C10 H10 108.4 . .
O1 C9 C5 123.07(14) . .
O1 C9 C10 118.01(14) . .
C5 C9 C10 118.92(13) . .
N4 C5 C6 106.32(14) . .
N4 C5 C9 122.58(14) . .
C6 C5 C9 131.00(15) . .
N4 C3 C2 101.29(14) . .
N4 C3 H3A 111.5 . .
C2 C3 H3A 111.5 . .
N4 C3 H3B 111.5 . .
C2 C3 H3B 111.5 . .
H3A C3 H3B 109.3 . .
C3 C2 C1 107.07(15) . .
C3 C2 H2A 110.3 . .
C1 C2 H2A 110.3 . .
C3 C2 H2B 110.3 . .
C1 C2 H2B 110.3 . .
H2A C2 H2B 108.6 . .
C8 C1 C2 102.60(15) . .
C8 C1 H1A 111.2 . .
C2 C1 H1A 111.2 . .
C8 C1 H1B 111.2 . .
C2 C1 H1B 111.2 . .
H1A C1 H1B 109.2 . .
N4 C8 C7 108.51(15) . .
N4 C8 C1 109.99(16) . .
C7 C8 C1 141.45(17) . .
C8 C7 C6 106.92(15) . .
C8 C7 H7 126.5 . .
C6 C7 H7 126.5 . .
C5 C6 C7 108.11(16) . .
C5 C6 H6A 125.9 . .
C7 C6 H6A 125.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C22 1.410(2) .
O6 H6 0.8200 .
O5 C21 1.424(2) .
O5 H5 0.8200 .
O4 C20 1.227(2) .
O3 C11 1.414(2) .
O3 H3 0.8200 .
O2 C10 1.412(2) .
O2 H2 0.83(3) .
O1 C9 1.2326(19) .
N15 C19 1.338(2) .
N15 C16 1.382(2) .
N15 C14 1.468(2) .
N4 C8 1.348(2) .
N4 C5 1.380(2) .
N4 C3 1.470(2) .
C22 C21 1.527(2) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C21 C20 1.535(2) .
C21 H21 0.9800 .
C20 C16 1.434(2) .
C16 C17 1.393(3) .
C14 C13 1.536(2) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C13 C12 1.505(4) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C19 C18 1.384(3) .
C19 C12 1.498(3) .
C18 C17 1.396(2) .
C18 H18 0.9300 .
C17 H17 0.9300 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C11 C10 1.526(2) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C10 C9 1.525(2) .
C10 H10 0.9800 .
C9 C5 1.441(2) .
C5 C6 1.397(2) .
C3 C2 1.529(3) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C2 C1 1.535(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 C8 1.490(3) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C8 C7 1.387(3) .
C7 C6 1.399(3) .
C7 H7 0.9300 .
C6 H6A 0.9300 .
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
O6 H6 O5 0.82 1.97 2.7855(16) 170.9 2_655
O5 H5 O4 0.82 2.06 2.5657(16) 119.2 .
O3 H3 O2 0.82 1.95 2.7714(18) 175.9 1_545
C21 H21 O6 0.98 2.52 3.367(2) 144.1 1_545
C17 H17 O6 0.93 2.63 3.509(2) 158.5 1_545
C3 H3A O1 0.97 2.61 3.385(2) 136.9 1_545
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
O6 C22 C21 O5 -63.41(18) . . . .
O6 C22 C21 C20 56.14(19) . . . .
O5 C21 C20 O4 10.5(2) . . . .
C22 C21 C20 O4 -110.05(18) . . . .
O5 C21 C20 C16 -168.92(15) . . . .
C22 C21 C20 C16 70.5(2) . . . .
C19 N15 C16 C17 -0.69(19) . . . .
C14 N15 C16 C17 174.27(18) . . . .
C19 N15 C16 C20 179.22(16) . . . .
C14 N15 C16 C20 -5.8(3) . . . .
O4 C20 C16 N15 6.7(3) . . . .
C21 C20 C16 N15 -173.87(16) . . . .
O4 C20 C16 C17 -173.38(18) . . . .
C21 C20 C16 C17 6.0(3) . . . .
C19 N15 C14 C13 -5.8(2) . . . .
C16 N15 C14 C13 179.40(19) . . . .
N15 C14 C13 C12 7.8(2) . . . .
C16 N15 C19 C18 0.4(2) . . . .
C14 N15 C19 C18 -175.70(16) . . . .
C16 N15 C19 C12 177.63(17) . . . .
C14 N15 C19 C12 1.5(2) . . . .
N15 C19 C18 C17 0.1(2) . . . .
C12 C19 C18 C17 -175.8(3) . . . .
N15 C16 C17 C18 0.7(2) . . . .
C20 C16 C17 C18 -179.19(17) . . . .
C19 C18 C17 C16 -0.5(2) . . . .
N15 C19 C12 C13 3.6(3) . . . .
C18 C19 C12 C13 179.5(2) . . . .
C14 C13 C12 C19 -7.1(3) . . . .
O3 C11 C10 O2 -63.78(17) . . . .
O3 C11 C10 C9 58.31(17) . . . .
O2 C10 C9 O1 11.31(19) . . . .
C11 C10 C9 O1 -111.02(16) . . . .
O2 C10 C9 C5 -168.33(13) . . . .
C11 C10 C9 C5 69.34(17) . . . .
C8 N4 C5 C6 -0.75(17) . . . .
C3 N4 C5 C6 -177.36(17) . . . .
C8 N4 C5 C9 -177.48(14) . . . .
C3 N4 C5 C9 5.9(3) . . . .
O1 C9 C5 N4 2.1(2) . . . .
C10 C9 C5 N4 -178.32(13) . . . .
O1 C9 C5 C6 -173.78(16) . . . .
C10 C9 C5 C6 5.8(2) . . . .
C8 N4 C3 C2 13.1(2) . . . .
C5 N4 C3 C2 -170.41(18) . . . .
N4 C3 C2 C1 -20.6(2) . . . .
C3 C2 C1 C8 20.9(2) . . . .
C5 N4 C8 C7 0.75(19) . . . .
C3 N4 C8 C7 178.13(14) . . . .
C5 N4 C8 C1 -177.33(13) . . . .
C3 N4 C8 C1 0.05(19) . . . .
C2 C1 C8 N4 -13.18(19) . . . .
C2 C1 C8 C7 169.7(2) . . . .
N4 C8 C7 C6 -0.4(2) . . . .
C1 C8 C7 C6 176.7(2) . . . .
N4 C5 C6 C7 0.47(19) . . . .
C9 C5 C6 C7 176.82(15) . . . .
C8 C7 C6 C5 0.0(2) . . . .
