#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/39/1503979.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_1503979
loop_
_publ_author_name
'Rasberry, Roger D.'
'Wu, Xiangyang'
'Bullock, Brooke N.'
'Smith, Mark D.'
'Shimizu, Ken D.'
_publ_section_title
;
 A small molecule diacid with long-term chiral memory.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2599
_journal_page_last               2602
_journal_paper_doi               10.1021/ol900955q
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C17 H11 N O6, C2 H3 N'
_chemical_formula_sum            'C19 H14 N2 O6'
_chemical_formula_weight         366.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.8310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8521(6)
_cell_length_b                   9.1835(3)
_cell_length_c                   13.5407(5)
_cell_measurement_reflns_used    7203
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.404
_cell_measurement_theta_min      2.671
_cell_volume                     1702.18(11)
_computing_cell_refinement       'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_data_collection       'SMART Version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus Version 6.45 (Bruker, 2001)'
_computing_molecular_graphics    various
_computing_publication_material  'SHELXTL Version 6.14 (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega 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  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20991
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0381
_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)+(0.0545P)²+0.2674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                2880
_reflns_number_total             3498
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900955q_si_002.cif
_cod_data_source_block           bbi57e
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1503979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.37435(10) 0.33037(15) 0.35462(11) 0.0226(3) Uani 1 1 d .
C2 C 0.40858(10) 0.24044(15) 0.45347(11) 0.0209(3) Uani 1 1 d .
C3 C 0.35179(10) 0.11541(15) 0.43462(11) 0.0194(3) Uani 1 1 d .
C4 C 0.27508(10) 0.12791(15) 0.32432(11) 0.0206(3) Uani 1 1 d .
C5 C 0.48316(11) 0.26935(16) 0.55139(11) 0.0249(3) Uani 1 1 d .
H5 H 0.5210 0.3558 0.5629 0.030 Uiso 1 1 calc R
C6 C 0.50039(11) 0.16690(16) 0.63200(12) 0.0263(3) Uani 1 1 d .
H6 H 0.5495 0.1846 0.7010 0.032 Uiso 1 1 calc R
C7 C 0.44662(10) 0.03877(16) 0.61285(11) 0.0236(3) Uani 1 1 d .
H7 H 0.4616 -0.0311 0.6687 0.028 Uiso 1 1 calc R
C8 C 0.37113(10) 0.00928(15) 0.51410(11) 0.0211(3) Uani 1 1 d .
C9 C 0.32134(11) -0.13577(16) 0.50232(12) 0.0240(3) Uani 1 1 d .
C10 C 0.23636(10) 0.30341(15) 0.17396(11) 0.0205(3) Uani 1 1 d .
C11 C 0.23011(10) 0.20884(15) 0.08977(11) 0.0203(3) Uani 1 1 d .
C12 C 0.16972(10) 0.24613(16) -0.01436(11) 0.0223(3) Uani 1 1 d .
H12 H 0.1623 0.1810 -0.0715 0.027 Uiso 1 1 calc R
C13 C 0.12023(11) 0.37773(16) -0.03546(12) 0.0262(3) Uani 1 1 d .
H13 H 0.0791 0.4029 -0.1068 0.031 Uiso 1 1 calc R
C14 C 0.13109(11) 0.47214(16) 0.04788(12) 0.0262(3) Uani 1 1 d .
H14 H 0.0989 0.5637 0.0322 0.031 Uiso 1 1 calc R
C15 C 0.18779(11) 0.43717(15) 0.15414(12) 0.0241(3) Uani 1 1 d .
C16 C 0.29072(10) 0.07305(15) 0.11005(11) 0.0215(3) Uani 1 1 d .
C17 C 0.19379(13) 0.54269(17) 0.24176(13) 0.0335(4) Uani 1 1 d .
H17A H 0.2516 0.6045 0.2585 0.050 Uiso 1 1 calc R
H17B H 0.1985 0.4885 0.3059 0.050 Uiso 1 1 calc R
H17C H 0.1351 0.6037 0.2177 0.050 Uiso 1 1 calc R
C18 C 0.00943(12) 0.7478(2) 0.32602(14) 0.0367(4) Uani 1 1 d .
C19 C 0.01991(13) 0.6339(2) 0.40370(15) 0.0440(4) Uani 1 1 d .
H19A H 0.0892 0.6217 0.4496 0.066 Uiso 1 1 calc R
H19B H -0.0059 0.5423 0.3662 0.066 Uiso 1 1 calc R
H19C H -0.0165 0.6606 0.4479 0.066 Uiso 1 1 calc R
N1 N 0.29021(9) 0.25923(12) 0.28256(9) 0.0212(3) Uani 1 1 d .
N2 N 0.00159(12) 0.8376(2) 0.26530(14) 0.0515(4) Uani 1 1 d .
O1 O 0.40823(8) 0.43992(11) 0.33481(8) 0.0302(3) Uani 1 1 d .
O2 O 0.20837(7) 0.04431(11) 0.27773(8) 0.0253(2) Uani 1 1 d .
O3 O 0.35004(8) -0.22458(11) 0.57449(9) 0.0355(3) Uani 1 1 d .
O4 O 0.24744(8) -0.16922(12) 0.41290(9) 0.0300(3) Uani 1 1 d .
O5 O 0.36385(8) 0.05230(11) 0.18843(8) 0.0305(3) Uani 1 1 d .
O6 O 0.25647(9) -0.02078(13) 0.02990(9) 0.0388(3) Uani 1 1 d .
H4A H 0.2296(14) -0.088(2) 0.3608(16) 0.055(6) Uiso 1 1 d .
H6A H 0.2927(17) -0.107(3) 0.0462(19) 0.079(8) 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 0.0033 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
O1 C1 N1 124.64(13)
O1 C1 C2 129.86(13)
N1 C1 C2 105.50(11)
C5 C2 C3 122.55(13)
C5 C2 C1 128.59(13)
C3 C2 C1 108.85(12)
C2 C3 C8 120.45(13)
C2 C3 C4 107.11(12)
C8 C3 C4 132.42(12)
O2 C4 N1 124.39(13)
O2 C4 C3 128.48(13)
N1 C4 C3 107.08(11)
C2 C5 C6 117.27(13)
C2 C5 H5 121.4
C6 C5 H5 121.4
C5 C6 C7 120.69(13)
C5 C6 H6 119.7
C7 C6 H6 119.7
C6 C7 C8 122.16(13)
C6 C7 H7 118.9
C8 C7 H7 118.9
C3 C8 C7 116.78(13)
C3 C8 C9 126.27(13)
C7 C8 C9 116.90(12)
O3 C9 O4 119.32(13)
O3 C9 C8 120.33(13)
O4 C9 C8 120.33(12)
C15 C10 C11 121.35(13)
C15 C10 N1 119.15(12)
C11 C10 N1 119.45(12)
C12 C11 C10 118.95(13)
C12 C11 C16 119.75(12)
C10 C11 C16 121.24(12)
C13 C12 C11 120.42(13)
C13 C12 H12 119.8
C11 C12 H12 119.8
C14 C13 C12 119.63(13)
C14 C13 H13 120.2
C12 C13 H13 120.2
C13 C14 C15 122.06(13)
C13 C14 H14 119.0
C15 C14 H14 119.0
C14 C15 C10 117.46(13)
C14 C15 C17 119.47(13)
C10 C15 C17 123.07(13)
O5 C16 O6 123.27(13)
O5 C16 C11 124.43(13)
O6 C16 C11 112.27(12)
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
N2 C18 C19 179.7(2)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C4 N1 C1 111.13(11)
C4 N1 C10 123.39(12)
C1 N1 C10 124.74(11)
C9 O4 H4A 112.2(12)
C16 O6 H6A 110.8(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2008(17)
C1 N1 1.4123(18)
C1 C2 1.4846(19)
C2 C5 1.384(2)
C2 C3 1.3885(19)
C3 C8 1.3967(19)
C3 C4 1.4904(19)
C4 O2 1.2181(17)
C4 N1 1.3867(18)
C5 C6 1.388(2)
C5 H5 0.9500
C6 C7 1.389(2)
C6 H6 0.9500
C7 C8 1.3982(19)
C7 H7 0.9500
C8 C9 1.502(2)
C9 O3 1.2160(17)
C9 O4 1.3167(17)
C10 C15 1.397(2)
C10 C11 1.4072(19)
C10 N1 1.4332(18)
C11 C12 1.389(2)
C11 C16 1.4997(19)
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.382(2)
C13 H13 0.9500
C14 C15 1.394(2)
C14 H14 0.9500
C15 C17 1.507(2)
C16 O5 1.2033(17)
C16 O6 1.3231(17)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 N2 1.138(2)
C18 C19 1.448(3)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
O4 H4A 0.99(2)
O6 H6A 0.94(3)
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
O4 H4A O2 0.99(2) 1.60(2) 2.5900(14) 176.1(18) .
O6 H6A O3 0.94(3) 1.73(3) 2.6671(15) 175(2) 4
O6 H6A O4 0.94(3) 2.64(2) 3.2354(15) 121.8(17) 4
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
O1 C1 C2 C5 7.1(3)
N1 C1 C2 C5 -173.71(13)
O1 C1 C2 C3 -173.60(14)
N1 C1 C2 C3 5.63(15)
C5 C2 C3 C8 -2.8(2)
C1 C2 C3 C8 177.79(12)
C5 C2 C3 C4 175.69(12)
C1 C2 C3 C4 -3.69(15)
C2 C3 C4 O2 -177.25(14)
C8 C3 C4 O2 1.0(2)
C2 C3 C4 N1 0.36(14)
C8 C3 C4 N1 178.63(14)
C3 C2 C5 C6 0.4(2)
C1 C2 C5 C6 179.63(13)
C2 C5 C6 C7 2.2(2)
C5 C6 C7 C8 -2.4(2)
C2 C3 C8 C7 2.58(19)
C4 C3 C8 C7 -175.50(13)
C2 C3 C8 C9 -174.84(13)
C4 C3 C8 C9 7.1(2)
C6 C7 C8 C3 -0.1(2)
C6 C7 C8 C9 177.61(13)
C3 C8 C9 O3 173.72(14)
C7 C8 C9 O3 -3.7(2)
C3 C8 C9 O4 -4.9(2)
C7 C8 C9 O4 177.69(12)
C15 C10 C11 C12 -3.8(2)
N1 C10 C11 C12 173.49(12)
C15 C10 C11 C16 173.30(12)
N1 C10 C11 C16 -9.39(19)
C10 C11 C12 C13 3.2(2)
C16 C11 C12 C13 -174.01(13)
C11 C12 C13 C14 -0.1(2)
C12 C13 C14 C15 -2.5(2)
C13 C14 C15 C10 1.8(2)
C13 C14 C15 C17 -177.82(14)
C11 C10 C15 C14 1.4(2)
N1 C10 C15 C14 -175.95(13)
C11 C10 C15 C17 -179.02(14)
N1 C10 C15 C17 3.7(2)
C12 C11 C16 O5 157.26(14)
C10 C11 C16 O5 -19.8(2)
C12 C11 C16 O6 -20.69(18)
C10 C11 C16 O6 162.20(13)
O2 C4 N1 C1 -178.93(13)
C3 C4 N1 C1 3.33(15)
O2 C4 N1 C10 -8.4(2)
C3 C4 N1 C10 173.90(11)
O1 C1 N1 C4 173.81(13)
C2 C1 N1 C4 -5.47(15)
O1 C1 N1 C10 3.4(2)
C2 C1 N1 C10 -175.89(12)
C15 C10 N1 C4 125.34(14)
C11 C10 N1 C4 -52.04(18)
C15 C10 N1 C1 -65.38(18)
C11 C10 N1 C1 117.24(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139038326
