#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/59/1555922.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_1555922
loop_
_publ_author_name
'Choi, Chulho'
'Nuhant, Philippe'
'Mousseau, James J.'
'Yang, Xiaojing'
'Gerstenberger, Brian S.'
'Williams, Jessica M.'
'Wright, Stephen W.'
_publ_section_title
;
 Synthesis of Chiral Azabicycles from Pyroglutaminols.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5748
_journal_page_last               5751
_journal_paper_doi               10.1021/acs.orglett.6b03024
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C10 H17 N O3'
_chemical_formula_weight         199.25
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.734(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.7737(6)
_cell_length_b                   7.9024(7)
_cell_length_c                   11.5568(9)
_cell_measurement_reflns_used    813
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      67.15
_cell_measurement_theta_min      3.89
_cell_volume                     518.07(8)
_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      123(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3826
_diffrn_reflns_theta_full        67.79
_diffrn_reflns_theta_max         67.79
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.6385
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       FLAT
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.0030(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.272
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.272
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0330
_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)+(0.0394P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                1339
_reflns_number_total             1429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03024_si_005.cif
_cod_data_source_block           z463_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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)
_cod_database_code               1555922
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
C1 C 0.9513(4) 0.3288(3) 0.72618(17) 0.0237(5) Uani 1 1 d .
H1A H 0.9254 0.3326 0.8084 0.028 Uiso 1 1 calc R
H1B H 1.1155 0.2934 0.7254 0.028 Uiso 1 1 calc R
C2 C 0.7723(4) 0.2140(3) 0.64896(17) 0.0232(5) Uani 1 1 d .
H2 H 0.8108 0.0907 0.6566 0.028 Uiso 1 1 calc R
C3 C 0.4818(4) 0.4185(3) 0.61313(18) 0.0256(5) Uani 1 1 d .
H3A H 0.4502 0.5053 0.6699 0.031 Uiso 1 1 calc R
H3B H 0.3422 0.4081 0.5492 0.031 Uiso 1 1 calc R
C4 C 0.7018(3) 0.4618(3) 0.56412(16) 0.0209(5) Uani 1 1 d .
H4 H 0.6813 0.5505 0.5013 0.025 Uiso 1 1 calc R
C5 C 0.7710(4) 0.2863(3) 0.52674(16) 0.0243(5) Uani 1 1 d .
H5A H 0.6503 0.2343 0.4649 0.029 Uiso 1 1 calc R
H5B H 0.9276 0.2836 0.5036 0.029 Uiso 1 1 calc R
C6 C 0.9389(3) 0.6476(3) 0.71167(15) 0.0195(4) Uani 1 1 d .
C7 C 1.2088(3) 0.7959(3) 0.86885(17) 0.0226(5) Uani 1 1 d .
C8 C 1.0192(4) 0.8934(3) 0.91696(18) 0.0276(5) Uani 1 1 d .
H8A H 0.9423 0.8180 0.9655 0.041 Uiso 1 1 calc R
H8B H 0.9017 0.9365 0.8513 0.041 Uiso 1 1 calc R
H8C H 1.0918 0.9884 0.9650 0.041 Uiso 1 1 calc R
C9 C 1.3217(4) 0.9019(3) 0.78490(18) 0.0267(5) Uani 1 1 d .
H9A H 1.2008 0.9371 0.7181 0.040 Uiso 1 1 calc R
H9B H 1.4421 0.8347 0.7562 0.040 Uiso 1 1 calc R
H9C H 1.3950 1.0022 0.8262 0.040 Uiso 1 1 calc R
C10 C 1.3933(4) 0.7272(3) 0.96913(18) 0.0306(5) Uani 1 1 d .
H10A H 1.5090 0.6600 0.9368 0.046 Uiso 1 1 calc R
H10B H 1.3165 0.6557 1.0202 0.046 Uiso 1 1 calc R
H10C H 1.4732 0.8217 1.0150 0.046 Uiso 1 1 calc R
N1 N 0.8944(3) 0.4919(2) 0.66539(13) 0.0214(4) Uani 1 1 d .
O1 O 0.5411(2) 0.25692(19) 0.67102(11) 0.0270(4) Uani 1 1 d .
O2 O 0.8426(2) 0.77603(17) 0.66832(10) 0.0235(4) Uani 1 1 d .
O3 O 1.1081(2) 0.64017(19) 0.81007(11) 0.0237(4) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0223(12) 0.0218(13) 0.0278(10) 0.0016(9) 0.0065(9) 0.0003(8)
C2 0.0228(13) 0.0166(12) 0.0320(10) 0.0005(8) 0.0096(9) 0.0010(8)
C3 0.0239(12) 0.0228(13) 0.0309(10) 0.0022(9) 0.0077(9) 0.0011(9)
C4 0.0212(12) 0.0202(12) 0.0217(9) 0.0007(8) 0.0053(8) -0.0018(9)
C5 0.0239(11) 0.0217(12) 0.0286(9) -0.0028(9) 0.0080(8) -0.0021(9)
C6 0.0171(11) 0.0213(12) 0.0228(9) 0.0006(9) 0.0108(8) -0.0021(8)
C7 0.0230(12) 0.0189(13) 0.0268(9) -0.0037(9) 0.0068(8) -0.0027(8)
C8 0.0272(13) 0.0289(13) 0.0280(10) -0.0049(9) 0.0087(9) -0.0022(9)
C9 0.0260(13) 0.0244(12) 0.0308(11) -0.0029(9) 0.0078(9) -0.0041(9)
C10 0.0285(13) 0.0287(14) 0.0331(11) -0.0004(10) 0.0015(9) -0.0029(9)
N1 0.0235(10) 0.0149(10) 0.0251(8) 0.0005(7) 0.0030(7) -0.0001(7)
O1 0.0229(8) 0.0253(9) 0.0355(7) 0.0051(6) 0.0122(6) -0.0029(6)
O2 0.0229(8) 0.0193(9) 0.0285(7) 0.0015(6) 0.0051(6) 0.0019(6)
O3 0.0237(9) 0.0188(8) 0.0274(7) -0.0006(6) 0.0021(6) -0.0010(6)
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
N1 C1 C2 100.00(15)
O1 C2 C5 103.33(16)
O1 C2 C1 107.67(16)
C5 C2 C1 101.81(17)
O1 C3 C4 103.15(16)
N1 C4 C3 107.38(15)
N1 C4 C5 99.95(15)
C3 C4 C5 100.42(16)
C2 C5 C4 91.99(15)
O2 C6 N1 123.96(17)
O2 C6 O3 125.6(2)
N1 C6 O3 110.37(18)
O3 C7 C9 110.26(15)
O3 C7 C10 102.36(16)
C9 C7 C10 111.16(17)
O3 C7 C8 110.00(16)
C9 C7 C8 112.12(19)
C10 C7 C8 110.52(16)
C6 N1 C1 126.85(15)
C6 N1 C4 121.46(15)
C1 N1 C4 107.75(16)
C2 O1 C3 105.74(15)
C6 O3 C7 120.81(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.475(3)
C1 C2 1.531(3)
C2 O1 1.445(3)
C2 C5 1.522(3)
C3 O1 1.452(2)
C3 C4 1.523(3)
C4 N1 1.476(2)
C4 C5 1.528(3)
C6 O2 1.220(3)
C6 N1 1.347(3)
C6 O3 1.356(2)
C7 O3 1.472(2)
C7 C9 1.518(3)
C7 C10 1.520(3)
C7 C8 1.526(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 60024802
