#------------------------------------------------------------------------------
#$Date: 2025-08-19 23:06:29 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301812 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025088.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_4025088
loop_
_publ_author_name
'David Marcoux'
'Sébastien R. Goudreau'
'André B. Charette'
_publ_section_title
;
trans-Directing Ability of the Amide Group: Enabling the Enantiocontrol in
the Synthesis of 1,1-Dicarboxy Cyclopropanes. Reaction Development, Scope,
and Synthetic Applications
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8939
_journal_page_last               8955
_journal_paper_doi               10.1021/jo902066y
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H16 O3'
_chemical_formula_sum            'C18 H16 O3'
_chemical_formula_weight         280.31
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 95.036(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1950(2)
_cell_length_b                   5.9546(1)
_cell_length_c                   17.0522(3)
_cell_measurement_reflns_used    10506
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.41
_cell_measurement_theta_min      3.89
_cell_volume                     1435.78(4)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006b)'
_computing_molecular_graphics    'SHELXTL v6.12 (Bruker AXS, 2001)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22947
_diffrn_reflns_theta_full        67.83
_diffrn_reflns_theta_max         67.83
_diffrn_reflns_theta_min         3.89
_diffrn_standards_decay_%        2.70
_diffrn_standards_interval_time  900
_diffrn_standards_number         147
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.7492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0355
_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)+(0.0660P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                2153
_reflns_number_total             2484
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo902066y_si_003.cif
_cod_data_source_block           cha187
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (23
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (33
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (46 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4025088
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.20376(9) 0.0706(2) 0.99184(7) 0.0310(3) Uani 1 1 d . . .
C2 C 0.19003(10) 0.1743(2) 0.90927(7) 0.0338(3) Uani 1 1 d . . .
H2 H 0.1327 0.1197 0.8766 0.041 Uiso 1 1 calc R . .
C3 C 0.16914(10) 0.3098(2) 0.97921(8) 0.0368(3) Uani 1 1 d . . .
H3A H 0.1020 0.3413 0.9865 0.044 Uiso 1 1 calc R . .
H3B H 0.2134 0.4327 0.9959 0.044 Uiso 1 1 calc R . .
O11 O 0.07504(7) -0.18831(15) 0.96913(5) 0.0423(3) Uani 1 1 d . . .
C11 C 0.13092(9) -0.0943(2) 1.01648(7) 0.0334(3) Uani 1 1 d . . .
C12 C 0.12834(9) -0.1280(2) 1.10316(7) 0.0343(3) Uani 1 1 d . . .
C13 C 0.16645(10) 0.0303(2) 1.15739(7) 0.0364(3) Uani 1 1 d . . .
H13 H 0.1952 0.1623 1.1392 0.044 Uiso 1 1 calc R . .
C14 C 0.16277(10) -0.0030(2) 1.23753(8) 0.0417(3) Uani 1 1 d . . .
H14 H 0.1878 0.1070 1.2740 0.050 Uiso 1 1 calc R . .
C15 C 0.12256(10) -0.1967(3) 1.26415(9) 0.0451(4) Uani 1 1 d . . .
H15 H 0.1202 -0.2206 1.3190 0.054 Uiso 1 1 calc R . .
C16 C 0.08571(11) -0.3555(2) 1.21101(9) 0.0453(4) Uani 1 1 d . . .
H16 H 0.0592 -0.4897 1.2297 0.054 Uiso 1 1 calc R . .
C17 C 0.08690(10) -0.3214(2) 1.13093(9) 0.0401(3) Uani 1 1 d . . .
H17 H 0.0595 -0.4296 1.0948 0.048 Uiso 1 1 calc R . .
C18 C 0.30335(9) 0.0330(2) 1.02304(7) 0.0301(3) Uani 1 1 d . . .
O18 O 0.36174(7) 0.17656(14) 1.03968(5) 0.0371(2) Uani 1 1 d . . .
O19 O 0.32143(6) -0.18795(13) 1.02774(5) 0.0352(2) Uani 1 1 d . . .
C19 C 0.41738(10) -0.2502(2) 1.05528(9) 0.0459(4) Uani 1 1 d . . .
H19A H 0.4608 -0.1979 1.0176 0.069 Uiso 1 1 calc R . .
H19B H 0.4218 -0.4140 1.0602 0.069 Uiso 1 1 calc R . .
H19C H 0.4344 -0.1810 1.1067 0.069 Uiso 1 1 calc R . .
C21 C 0.27274(9) 0.2240(2) 0.86355(7) 0.0318(3) Uani 1 1 d . . .
C22 C 0.29978(9) 0.0654(2) 0.80971(7) 0.0349(3) Uani 1 1 d . . .
H22 H 0.2684 -0.0755 0.8054 0.042 Uiso 1 1 calc R . .
C23 C 0.37168(10) 0.1108(2) 0.76263(8) 0.0383(3) Uani 1 1 d . . .
H23 H 0.3888 0.0016 0.7258 0.046 Uiso 1 1 calc R . .
C24 C 0.41928(10) 0.3149(2) 0.76851(8) 0.0379(3) Uani 1 1 d . . .
H24 H 0.4684 0.3463 0.7357 0.045 Uiso 1 1 calc R . .
C25 C 0.39405(10) 0.4718(2) 0.82284(8) 0.0378(3) Uani 1 1 d . . .
H25 H 0.4268 0.6108 0.8281 0.045 Uiso 1 1 calc R . .
C26 C 0.32124(10) 0.4268(2) 0.86956(7) 0.0361(3) Uani 1 1 d . . .
H26 H 0.3042 0.5364 0.9063 0.043 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 0.0181 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'
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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C18 C1 C11 . . . 117.12(10) y
C18 C1 C3 . . . 118.66(11) y
C11 C1 C3 . . . 115.38(11) y
C18 C1 C2 . . . 115.48(11) y
C11 C1 C2 . . . 118.80(11) y
C3 C1 C2 . . . 58.53(8) y
C3 C2 C21 . . . 122.04(11) y
C3 C2 C1 . . . 60.13(8) y
C21 C2 C1 . . . 121.07(11) y
C3 C2 H2 . . . 114.3 ?
C21 C2 H2 . . . 114.3 ?
C1 C2 H2 . . . 114.3 ?
C2 C3 C1 . . . 61.34(8) y
C2 C3 H3A . . . 117.6 ?
C1 C3 H3A . . . 117.6 ?
C2 C3 H3B . . . 117.6 ?
C1 C3 H3B . . . 117.6 ?
H3A C3 H3B . . . 114.7 ?
O11 C11 C12 . . . 121.53(12) y
O11 C11 C1 . . . 122.41(11) y
C12 C11 C1 . . . 116.01(11) y
C17 C12 C13 . . . 118.90(12) y
C17 C12 C11 . . . 119.60(12) y
C13 C12 C11 . . . 121.50(12) y
C14 C13 C12 . . . 120.69(13) y
C14 C13 H13 . . . 119.7 ?
C12 C13 H13 . . . 119.7 ?
C15 C14 C13 . . . 119.73(14) y
C15 C14 H14 . . . 120.1 ?
C13 C14 H14 . . . 120.1 ?
C16 C15 C14 . . . 119.99(13) y
C16 C15 H15 . . . 120 ?
C14 C15 H15 . . . 120 ?
C15 C16 C17 . . . 120.75(13) y
C15 C16 H16 . . . 119.6 ?
C17 C16 H16 . . . 119.6 ?
C16 C17 C12 . . . 119.91(14) y
C16 C17 H17 . . . 120 ?
C12 C17 H17 . . . 120 ?
O18 C18 O19 . . . 123.83(12) y
O18 C18 C1 . . . 126.21(11) y
O19 C18 C1 . . . 109.92(10) y
C18 O19 C19 . . . 116.09(10) y
O19 C19 H19A . . . 109.5 ?
O19 C19 H19B . . . 109.5 ?
H19A C19 H19B . . . 109.5 ?
O19 C19 H19C . . . 109.5 ?
H19A C19 H19C . . . 109.5 ?
H19B C19 H19C . . . 109.5 ?
C26 C21 C22 . . . 118.30(12) y
C26 C21 C2 . . . 122.71(12) y
C22 C21 C2 . . . 118.92(12) y
C23 C22 C21 . . . 120.71(12) y
C23 C22 H22 . . . 119.6 ?
C21 C22 H22 . . . 119.6 ?
C22 C23 C24 . . . 120.62(12) y
C22 C23 H23 . . . 119.7 ?
C24 C23 H23 . . . 119.7 ?
C25 C24 C23 . . . 119.06(13) y
C25 C24 H24 . . . 120.5 ?
C23 C24 H24 . . . 120.5 ?
C24 C25 C26 . . . 120.28(12) y
C24 C25 H25 . . . 119.9 ?
C26 C25 H25 . . . 119.9 ?
C25 C26 C21 . . . 121.02(12) y
C25 C26 H26 . . . 119.5 ?
C21 C26 H26 . . . 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C18 . . 1.4832(18) y
C1 C11 . . 1.5119(18) y
C1 C3 . . 1.5160(17) y
C1 C2 . . 1.5342(16) y
C2 C3 . . 1.4911(18) y
C2 C21 . . 1.4948(19) y
C2 H2 . . 1 ?
C3 H3a . . 0.99 ?
C3 H3b . . 0.99 ?
O11 C11 . . 1.2172(16) y
C11 C12 . . 1.4953(17) y
C12 C17 . . 1.3947(19) y
C12 C13 . . 1.3960(19) y
C13 C14 . . 1.3864(18) y
C13 H13 . . 0.95 ?
C14 C15 . . 1.381(2) y
C14 H14 . . 0.95 ?
C15 C16 . . 1.381(2) y
C15 H15 . . 0.95 ?
C16 C17 . . 1.382(2) y
C16 H16 . . 0.95 ?
C17 H17 . . 0.95 ?
C18 O18 . . 1.2071(15) y
C18 O19 . . 1.3415(14) y
O19 C19 . . 1.4494(16) y
C19 H19a . . 0.98 ?
C19 H19b . . 0.98 ?
C19 H19c . . 0.98 ?
C21 C26 . . 1.3897(18) y
C21 C22 . . 1.3944(18) y
C22 C23 . . 1.380(2) y
C22 H22 . . 0.95 ?
C23 C24 . . 1.3896(19) y
C23 H23 . . 0.95 ?
C24 C25 . . 1.3847(19) y
C24 H24 . . 0.95 ?
C25 C26 . . 1.385(2) y
C25 H25 . . 0.95 ?
C26 H26 . . 0.95 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 C1 C2 C3 . . . . -109.34(12) y
C11 C1 C2 C3 . . . . 103.71(13) y
C18 C1 C2 C21 . . . . 2.27(16) y
C11 C1 C2 C21 . . . . -144.68(12) y
C3 C1 C2 C21 . . . . 111.61(14) y
C21 C2 C3 C1 . . . . -110.03(13) y
C18 C1 C3 C2 . . . . 103.91(13) y
C11 C1 C3 C2 . . . . -109.55(12) y
C18 C1 C11 O11 . . . . -128.67(13) y
C3 C1 C11 O11 . . . . 84.26(15) y
C2 C1 C11 O11 . . . . 17.75(18) y
C18 C1 C11 C12 . . . . 54.06(15) y
C3 C1 C11 C12 . . . . -93.01(13) y
C2 C1 C11 C12 . . . . -159.52(11) y
O11 C11 C12 C17 . . . . 22.96(19) y
C1 C11 C12 C17 . . . . -159.74(12) y
O11 C11 C12 C13 . . . . -156.93(13) y
C1 C11 C12 C13 . . . . 20.37(18) y
C17 C12 C13 C14 . . . . -0.4(2) y
C11 C12 C13 C14 . . . . 179.51(12) y
C12 C13 C14 C15 . . . . 1.2(2) y
C13 C14 C15 C16 . . . . -0.4(2) y
C14 C15 C16 C17 . . . . -1.2(2) y
C15 C16 C17 C12 . . . . 2.0(2) y
C13 C12 C17 C16 . . . . -1.2(2) y
C11 C12 C17 C16 . . . . 178.89(12) y
C11 C1 C18 O18 . . . . -146.32(12) y
C3 C1 C18 O18 . . . . -0.35(18) y
C2 C1 C18 O18 . . . . 66.16(16) y
C11 C1 C18 O19 . . . . 36.01(14) y
C3 C1 C18 O19 . . . . -178.02(10) y
C2 C1 C18 O19 . . . . -111.51(11) y
O18 C18 O19 C19 . . . . 0.53(17) y
C1 C18 O19 C19 . . . . 178.27(10) y
C3 C2 C21 C26 . . . . -16.51(18) y
C1 C2 C21 C26 . . . . -88.52(15) y
C3 C2 C21 C22 . . . . 166.74(11) y
C1 C2 C21 C22 . . . . 94.74(14) y
C26 C21 C22 C23 . . . . -1.21(18) y
C2 C21 C22 C23 . . . . 175.68(11) y
C21 C22 C23 C24 . . . . 0.67(19) y
C22 C23 C24 C25 . . . . 0.51(19) y
C23 C24 C25 C26 . . . . -1.13(19) y
C24 C25 C26 C21 . . . . 0.58(19) y
C22 C21 C26 C25 . . . . 0.59(18) y
C2 C21 C26 C25 . . . . -176.18(11) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139091360
