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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/1/55/48/1554897.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_1554897
loop_
_publ_author_name
'Mandzhulo, Aleksandr'
'Vashchenko, Iryna'
'Gerasov, Andrii'
'Vovk, Mykhaylo'
'Rusanov, Eduard'
'Fetyukhin, Volodymyr'
'Lukin, Oleg'
'Shivanyuk, Alexander'
_publ_section_title
;
 Selective synthesis of N-protected
 exo-spiro[oxirane-3,2′-tropanes]
;
_journal_issue                   10
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1692
_journal_paper_doi               10.1039/C9QO00377K
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_chemical_melting_point          376.8(8)
_chemical_name_systematic
'Benzyl 8-azaspiro[bicyclo[3.2.1]octane-(exo)-3,2?-oxirane]-8-carboxylate'
_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-2016/4
_audit_update_record
;
2017-11-29 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.580(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9218(11)
_cell_length_b                   6.5193(8)
_cell_length_c                   13.4340(16)
_cell_measurement_reflns_used    1347
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      2.62
_cell_volume                     679.67(15)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         1.547
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2672
_reflns_number_total             2956
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qo00377k2.cif
_cod_data_source_block           v900
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '376-377.5' was changed to
'376.8(8)' -- the average value was taken and precision was
estimated.

data item '_exptl_absorpt_correction_type' value 'Numerical' was
changed to 'numerical' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/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      'P 21'
_cod_database_code               1554897
_shelx_shelxl_version_number     2016/4
_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.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.980
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
C1 C 0.7722(2) -0.0273(3) 0.67391(14) 0.0238(4) Uani 1 1 d . .
H1 H 0.773333 -0.163930 0.704440 0.029 Uiso 1 1 calc R U
C2 C 0.8522(2) 0.1336(3) 0.75195(14) 0.0253(4) Uani 1 1 d . .
H2A H 0.786212 0.142753 0.805325 0.030 Uiso 1 1 calc R U
H2B H 0.969161 0.094317 0.782575 0.030 Uiso 1 1 calc R U
C3 C 0.8527(2) 0.3388(3) 0.70000(15) 0.0240(4) Uani 1 1 d . .
C4 C 0.6835(2) 0.3963(3) 0.63139(15) 0.0252(4) Uani 1 1 d . .
H4A H 0.700298 0.513196 0.589780 0.030 Uiso 1 1 calc R U
H4B H 0.600234 0.434051 0.672142 0.030 Uiso 1 1 calc R U
C5 C 0.6162(2) 0.2142(3) 0.56352(14) 0.0241(4) Uani 1 1 d . .
H5 H 0.507885 0.247407 0.516790 0.029 Uiso 1 1 calc R U
C6 C 0.8551(3) -0.0288(3) 0.57960(15) 0.0282(4) Uani 1 1 d . .
H6A H 0.846526 -0.163786 0.548656 0.034 Uiso 1 1 calc R U
H6B H 0.975595 0.009809 0.597623 0.034 Uiso 1 1 calc R U
C7 C 0.7516(2) 0.1304(3) 0.50641(15) 0.0277(4) Uani 1 1 d . .
H7A H 0.826218 0.239526 0.491714 0.033 Uiso 1 1 calc R U
H7B H 0.696616 0.066080 0.443078 0.033 Uiso 1 1 calc R U
C8 C 1.0144(3) 0.4217(3) 0.68020(16) 0.0319(5) Uani 1 1 d . .
H8A H 1.117015 0.337586 0.698174 0.038 Uiso 1 1 calc R U
H8B H 1.009055 0.505990 0.620143 0.038 Uiso 1 1 calc R U
C9 C 0.4510(2) 0.0041(3) 0.66261(14) 0.0234(4) Uani 1 1 d . .
C10 C 0.3269(3) -0.1982(3) 0.77611(16) 0.0323(5) Uani 1 1 d . .
H10A H 0.338685 -0.340411 0.797563 0.039 Uiso 1 1 calc R U
H10B H 0.225532 -0.187676 0.722193 0.039 Uiso 1 1 calc R U
C11 C 0.3009(2) -0.0682(3) 0.86431(15) 0.0273(5) Uani 1 1 d . .
C12 C 0.3699(3) 0.1258(4) 0.88202(16) 0.0331(5) Uani 1 1 d . .
H12 H 0.436740 0.180069 0.838862 0.040 Uiso 1 1 calc R U
C13 C 0.3403(3) 0.2405(4) 0.96379(17) 0.0437(6) Uani 1 1 d . .
H13 H 0.387463 0.370971 0.975644 0.052 Uiso 1 1 calc R U
C14 C 0.2401(3) 0.1598(5) 1.02767(18) 0.0497(7) Uani 1 1 d . .
H14 H 0.220446 0.235715 1.082849 0.060 Uiso 1 1 calc R U
C15 C 0.1696(3) -0.0327(5) 1.00954(17) 0.0454(7) Uani 1 1 d . .
H15 H 0.101403 -0.086062 1.052172 0.055 Uiso 1 1 calc R U
C16 C 0.1996(3) -0.1473(4) 0.92809(15) 0.0340(5) Uani 1 1 d . .
H16 H 0.151755 -0.277437 0.916169 0.041 Uiso 1 1 calc R U
N1 N 0.59596(19) 0.0392(2) 0.62848(12) 0.0230(4) Uani 1 1 d . .
O1 O 0.94036(19) 0.5030(2) 0.76171(10) 0.0340(4) Uani 1 1 d . .
O2 O 0.31283(16) 0.0863(2) 0.62991(10) 0.0323(4) Uani 1 1 d . .
O3 O 0.47664(17) -0.1396(2) 0.73660(10) 0.0300(3) 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 0.0033 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
N1 C1 C2 108.09(15)
N1 C1 C6 100.73(15)
C2 C1 C6 112.50(16)
C3 C2 C1 109.30(14)
O1 C3 C8 59.52(13)
O1 C3 C2 115.92(15)
C8 C3 C2 119.67(17)
O1 C3 C4 115.58(16)
C8 C3 C4 119.91(18)
C2 C3 C4 114.63(16)
C3 C4 C5 109.41(16)
N1 C5 C4 108.47(14)
N1 C5 C7 101.00(16)
C4 C5 C7 112.25(16)
C1 C6 C7 105.08(15)
C5 C7 C6 104.76(16)
O1 C8 C3 59.56(13)
O2 C9 N1 124.85(18)
O2 C9 O3 124.17(17)
N1 C9 O3 110.95(16)
O3 C10 C11 113.14(16)
C12 C11 C16 119.5(2)
C12 C11 C10 122.70(18)
C16 C11 C10 117.73(19)
C11 C12 C13 120.4(2)
C14 C13 C12 119.7(3)
C15 C14 C13 120.0(2)
C14 C15 C16 120.3(2)
C15 C16 C11 120.0(2)
C9 N1 C5 122.74(16)
C9 N1 C1 127.95(16)
C5 N1 C1 105.57(14)
C8 O1 C3 60.92(12)
C9 O3 C10 116.11(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.472(2)
C1 C2 1.528(3)
C1 C6 1.539(3)
C2 C3 1.510(3)
C3 O1 1.443(2)
C3 C8 1.463(3)
C3 C4 1.513(3)
C4 C5 1.526(3)
C5 N1 1.465(2)
C5 C7 1.539(3)
C6 C7 1.546(3)
C8 O1 1.443(3)
C9 O2 1.218(2)
C9 N1 1.339(2)
C9 O3 1.351(2)
C10 O3 1.445(2)
C10 C11 1.504(3)
C11 C12 1.379(3)
C11 C16 1.386(3)
C12 C13 1.387(3)
C13 C14 1.384(4)
C14 C15 1.375(4)
C15 C16 1.385(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 25140563
