#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:45:56 +0300 (Mon, 04 May 2020) $
#$Revision: 251476 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038269.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_4038269
loop_
_publ_author_name
'Castán, Alejandro'
'Badorrey, Ramón'
'Díez, José A'
'Christoffersen, Claus T.'
'Rasmussen, Lars K.'
'Kehler, Jan'
'Köhler, Ralf'
'Gálvez, José A'
'Díaz-de-Villegas, María D'
_publ_section_title
;
 Debenzylative Cycloetherification as a Synthetic Tool in the
 Diastereoselective Synthesis of 3,6-Disubstituted
 Hexahydro-2H-furo[3,2-b]pyrroles, PDE1 Enzyme Inhibitors
 with an Antiproliferative Effect on Melanoma Cells.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5941
_journal_page_last               5951
_journal_paper_doi               10.1021/acs.joc.0c00276
_journal_volume                  85
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H25 N O5'
_chemical_formula_sum            'C18 H25 N O5'
_chemical_formula_weight         335.39
_chemical_name_systematic
; 
tert-butyl (3S,3aS,6R,6aR)-3-(benzyloxy)-6-hydroxyhexahydro-4H-furo[3,2-b]pyrrole-4-carboxylate 
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6708(15)
_cell_length_b                   11.5329(18)
_cell_length_c                   17.874(3)
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2400
_cell_measurement_theta_min      3.4600
_cell_volume                     1787.4(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14059
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.4050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                3135
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0c00276_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038269.cif.
;
_cod_database_code               4038269
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0229(2) 0.13168(16) 1.08622(10) 0.0576(5) Uani 1 1 d . . .
O2 O 1.1832(2) -0.11432(17) 0.98933(11) 0.0565(5) Uani 1 1 d . . .
H2O H 1.210(5) -0.187(3) 1.010(2) 0.096(12) Uiso 1 1 d . . .
O3 O 0.9327(2) 0.27894(13) 0.95692(9) 0.0485(5) Uani 1 1 d . . .
O4 O 0.6914(2) -0.17240(14) 0.94181(10) 0.0541(5) Uani 1 1 d . . .
O5 O 0.7278(2) -0.00689(14) 0.87586(9) 0.0490(4) Uani 1 1 d . . .
N1 N 0.8622(2) -0.03705(15) 0.97902(10) 0.0379(5) Uani 1 1 d . . .
C1 C 0.9500(3) 0.06901(18) 0.96503(13) 0.0376(5) Uani 1 1 d . . .
H1 H 0.9912 0.0722 0.9140 0.045 Uiso 1 1 calc R . .
C2 C 1.0775(3) 0.06504(19) 1.02416(13) 0.0422(5) Uani 1 1 d . . .
H2 H 1.1751 0.0956 1.0047 0.051 Uiso 1 1 calc R . .
C3 C 1.0913(3) -0.0623(2) 1.04519(14) 0.0432(5) Uani 1 1 d . . .
H3 H 1.1353 -0.0727 1.0952 0.052 Uiso 1 1 calc R . .
C4 C 0.9262(3) -0.10441(19) 1.04097(13) 0.0433(6) Uani 1 1 d . . .
H4A H 0.9219 -0.1869 1.0305 0.052 Uiso 1 1 calc R . .
H4B H 0.8715 -0.0888 1.0872 0.052 Uiso 1 1 calc R . .
C5 C 0.8599(3) 0.17792(19) 0.98557(13) 0.0413(5) Uani 1 1 d . . .
H5 H 0.7518 0.1728 0.9698 0.050 Uiso 1 1 calc R . .
C6 C 0.8751(3) 0.1797(2) 1.06946(15) 0.0533(7) Uani 1 1 d . . .
H6A H 0.8679 0.2585 1.0881 0.064 Uiso 1 1 calc R . .
H6B H 0.7941 0.1338 1.0924 0.064 Uiso 1 1 calc R . .
C7 C 0.9031(4) 0.2968(2) 0.87953(14) 0.0566(7) Uani 1 1 d . . .
H7A H 0.7971 0.2760 0.8684 0.068 Uiso 1 1 calc R . .
H7B H 0.9700 0.2472 0.8501 0.068 Uiso 1 1 calc R . .
C8 C 0.9302(3) 0.42072(19) 0.85868(13) 0.0424(6) Uani 1 1 d . . .
C9 C 0.9912(3) 0.5013(2) 0.90684(15) 0.0505(6) Uani 1 1 d . . .
H9 H 1.0212 0.4788 0.9546 0.061 Uiso 1 1 calc R . .
C10 C 1.0086(4) 0.6157(2) 0.88494(17) 0.0594(7) Uani 1 1 d . . .
H10 H 1.0501 0.6696 0.9180 0.071 Uiso 1 1 calc R . .
C11 C 0.9652(4) 0.6493(3) 0.81523(19) 0.0694(9) Uani 1 1 d . . .
H11 H 0.9769 0.7261 0.8005 0.083 Uiso 1 1 calc R . .
C12 C 0.9042(4) 0.5701(3) 0.76676(18) 0.0750(9) Uani 1 1 d . . .
H12 H 0.8733 0.5933 0.7192 0.090 Uiso 1 1 calc R . .
C13 C 0.8885(4) 0.4565(2) 0.78791(16) 0.0602(8) Uani 1 1 d . . .
H13 H 0.8491 0.4029 0.7541 0.072 Uiso 1 1 calc R . .
C14 C 0.7551(3) -0.07984(19) 0.93298(13) 0.0387(5) Uani 1 1 d . . .
C15 C 0.6029(3) -0.0293(2) 0.82180(14) 0.0528(7) Uani 1 1 d . . .
C16 C 0.6074(5) 0.0782(3) 0.77368(19) 0.0863(11) Uani 1 1 d . . .
H16A H 0.5835 0.1448 0.8037 0.129 Uiso 1 1 calc R . .
H16B H 0.5330 0.0712 0.7342 0.129 Uiso 1 1 calc R . .
H16C H 0.7085 0.0868 0.7526 0.129 Uiso 1 1 calc R . .
C17 C 0.4523(4) -0.0371(4) 0.8628(2) 0.0893(12) Uani 1 1 d . . .
H17A H 0.4505 -0.1066 0.8923 0.134 Uiso 1 1 calc R . .
H17B H 0.3691 -0.0389 0.8273 0.134 Uiso 1 1 calc R . .
H17C H 0.4409 0.0291 0.8948 0.134 Uiso 1 1 calc R . .
C18 C 0.6393(6) -0.1355(3) 0.77678(19) 0.0987(14) Uani 1 1 d . . .
H18A H 0.6344 -0.2026 0.8084 0.148 Uiso 1 1 calc R . .
H18B H 0.7410 -0.1286 0.7561 0.148 Uiso 1 1 calc R . .
H18C H 0.5657 -0.1431 0.7370 0.148 Uiso 1 1 calc R . .
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
C6 O1 C2 110.07(19) . . ?
C3 O2 H2O 104(2) . . ?
C5 O3 C7 112.89(19) . . ?
C14 O5 C15 121.17(19) . . ?
C14 N1 C4 122.30(18) . . ?
C14 N1 C1 124.45(18) . . ?
C4 N1 C1 112.12(18) . . ?
N1 C1 C5 112.42(19) . . ?
N1 C1 C2 103.47(17) . . ?
C5 C1 C2 103.23(18) . . ?
N1 C1 H1 112.3 . . ?
C5 C1 H1 112.3 . . ?
C2 C1 H1 112.3 . . ?
O1 C2 C3 110.7(2) . . ?
O1 C2 C1 106.26(19) . . ?
C3 C2 C1 104.85(18) . . ?
O1 C2 H2 111.6 . . ?
C3 C2 H2 111.6 . . ?
C1 C2 H2 111.6 . . ?
O2 C3 C4 111.3(2) . . ?
O2 C3 C2 106.3(2) . . ?
C4 C3 C2 102.91(19) . . ?
O2 C3 H3 112.0 . . ?
C4 C3 H3 112.0 . . ?
C2 C3 H3 112.0 . . ?
N1 C4 C3 103.06(19) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O3 C5 C6 108.0(2) . . ?
O3 C5 C1 111.16(19) . . ?
C6 C5 C1 101.91(19) . . ?
O3 C5 H5 111.8 . . ?
C6 C5 H5 111.8 . . ?
C1 C5 H5 111.8 . . ?
O1 C6 C5 106.4(2) . . ?
O1 C6 H6A 110.4 . . ?
C5 C6 H6A 110.4 . . ?
O1 C6 H6B 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O3 C7 C8 110.6(2) . . ?
O3 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C7 123.4(2) . . ?
C13 C8 C7 118.3(2) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.9(3) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
O4 C14 N1 124.2(2) . . ?
O4 C14 O5 124.7(2) . . ?
N1 C14 O5 111.07(18) . . ?
O5 C15 C18 109.9(3) . . ?
O5 C15 C17 109.3(2) . . ?
C18 C15 C17 113.4(3) . . ?
O5 C15 C16 102.1(2) . . ?
C18 C15 C16 111.1(3) . . ?
C17 C15 C16 110.5(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C6 1.428(3) . ?
O1 C2 1.430(3) . ?
O2 C3 1.412(3) . ?
O2 H2O 0.94(4) . ?
O3 C5 1.421(3) . ?
O3 C7 1.422(3) . ?
O4 C14 1.213(3) . ?
O5 C14 1.344(3) . ?
O5 C15 1.475(3) . ?
N1 C14 1.335(3) . ?
N1 C4 1.462(3) . ?
N1 C1 1.462(3) . ?
C1 C5 1.524(3) . ?
C1 C2 1.530(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.521(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.514(3) . ?
C3 H3 0.9800 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(3) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.496(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.373(3) . ?
C8 C13 1.379(4) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 C18 1.499(4) . ?
C15 C17 1.500(5) . ?
C15 C16 1.509(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
