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#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503109.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_1503109
loop_
_publ_author_name
'Colquhoun, Howard M.'
'Zhu, Zhixue'
'Cardin, Christine J.'
'White, Andrew J. P.'
'Drew, Michael G. B.'
'Gan, Yu'
_publ_section_title
;
 Bis(hydroxy-isoindolinone)s: synthesis, stereochemistry, polymer
 chemistry, and supramolecular assembly.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3756
_journal_page_last               3759
_journal_paper_doi               10.1021/ol101338m
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C48 H54 F2 N6 O8'
_chemical_formula_weight         880.97
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.667(13)
_cell_angle_beta                 92.869(18)
_cell_angle_gamma                96.670(17)
_cell_formula_units_Z            1
_cell_length_a                   8.572(3)
_cell_length_b                   9.6617(15)
_cell_length_c                   13.723(2)
_cell_measurement_reflns_used    6637
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.51
_cell_volume                     1124.6(5)
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.822
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6637
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.944
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0586
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
_refine_ls_weighting_details 
  w=1/[σ²(Fo²)+(0.1319P)²+0.0000P] where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.1964
_reflns_number_gt                3187
_reflns_number_total             5385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101338m_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        1124.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C48 H54 F2 N6 O8 '
_cod_database_code               1503109
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.16146(19) 0.87776(17) 0.36797(13) 0.0218(4) Uani 1 1 d .
C2 C 0.1818(2) 0.8736(2) 0.46749(16) 0.0224(5) Uani 1 1 d .
O2 O 0.08427(17) 0.82272(16) 0.52217(11) 0.0298(4) Uani 1 1 d .
C3 C 0.3459(2) 0.9412(2) 0.49539(16) 0.0213(5) Uani 1 1 d .
C4 C 0.4254(2) 0.9609(2) 0.58775(16) 0.0216(5) Uani 1 1 d .
H4 H 0.3772 0.9354 0.6442 0.026 Uiso 1 1 calc R
C5 C 0.4184(2) 0.9787(2) 0.41028(16) 0.0211(5) Uani 1 1 d .
C6 C 0.3034(2) 0.9420(2) 0.32091(16) 0.0213(5) Uani 1 1 d .
O6 O 0.35670(17) 0.84762(15) 0.25255(11) 0.0253(4) Uani 1 1 d .
H6 H 0.3899 0.7838 0.2808 0.030 Uiso 1 1 calc R
C11 C 0.0251(2) 0.8088(2) 0.31081(16) 0.0223(5) Uani 1 1 d .
C12 C 0.0252(3) 0.6714(2) 0.27356(18) 0.0290(5) Uani 1 1 d .
H12 H 0.1122 0.6246 0.2859 0.035 Uiso 1 1 calc R
C13 C -0.1052(3) 0.6041(2) 0.21787(18) 0.0331(6) Uani 1 1 d .
H13 H -0.1046 0.5118 0.1941 0.040 Uiso 1 1 calc R
C14 C -0.2364(3) 0.6717(3) 0.19692(17) 0.0300(5) Uani 1 1 d .
C15 C -0.2345(3) 0.8090(2) 0.23414(17) 0.0299(5) Uani 1 1 d .
H15 H -0.3207 0.8564 0.2209 0.036 Uiso 1 1 calc R
C16 C -0.1042(3) 0.8776(2) 0.29159(17) 0.0277(5) Uani 1 1 d .
H16 H -0.1053 0.9692 0.3166 0.033 Uiso 1 1 calc R
C17 C -0.3782(3) 0.5992(3) 0.1345(2) 0.0439(7) Uani 1 1 d .
H17A H -0.4639 0.6546 0.1388 0.066 Uiso 1 1 calc R
H17B H -0.4089 0.5090 0.1578 0.066 Uiso 1 1 calc R
H17C H -0.3510 0.5883 0.0677 0.066 Uiso 1 1 calc R
C21 C 0.2713(2) 1.0729(2) 0.27021(16) 0.0222(5) Uani 1 1 d .
C22 C 0.1787(3) 1.1660(2) 0.31264(17) 0.0262(5) Uani 1 1 d .
H22 H 0.1324 1.1463 0.3708 0.031 Uiso 1 1 calc R
C23 C 0.1542(3) 1.2887(2) 0.26907(19) 0.0327(6) Uani 1 1 d .
H23 H 0.0907 1.3503 0.2970 0.039 Uiso 1 1 calc R
C24 C 0.2255(3) 1.3167(2) 0.18430(19) 0.0364(6) Uani 1 1 d .
C25 C 0.3198(3) 1.2282(3) 0.1410(2) 0.0394(6) Uani 1 1 d .
H25 H 0.3675 1.2500 0.0837 0.047 Uiso 1 1 calc R
C26 C 0.3428(3) 1.1053(2) 0.18422(18) 0.0327(6) Uani 1 1 d .
H26 H 0.4064 1.0444 0.1556 0.039 Uiso 1 1 calc R
F27 F 0.2008(2) 1.43528(16) 0.13975(13) 0.0554(5) Uani 1 1 d .
C31 C 0.7970(3) 0.5352(3) 0.4707(2) 0.0467(7) Uani 1 1 d .
H31A H 0.8731 0.4952 0.4321 0.070 Uiso 1 1 calc R
H31B H 0.7825 0.4849 0.5283 0.070 Uiso 1 1 calc R
H31C H 0.8338 0.6314 0.4893 0.070 Uiso 1 1 calc R
N32 N 0.6471(2) 0.5262(2) 0.41322(15) 0.0305(5) Uani 1 1 d .
C33 C 0.5838(3) 0.3883(3) 0.3690(2) 0.0411(6) Uani 1 1 d .
H33A H 0.5653 0.3249 0.4194 0.062 Uiso 1 1 calc R
H33B H 0.6578 0.3545 0.3258 0.062 Uiso 1 1 calc R
H33C H 0.4866 0.3948 0.3326 0.062 Uiso 1 1 calc R
C34 C 0.5740(3) 0.6365(3) 0.40020(19) 0.0367(6) Uani 1 1 d .
H34 H 0.6220 0.7223 0.4278 0.044 Uiso 1 1 calc R
O35 O 0.4439(2) 0.63447(18) 0.35313(14) 0.0424(5) Uani 1 1 d .
C41 C 0.9720(5) 0.1768(7) -0.0246(3) 0.120(2) Uani 1 1 d .
H41A H 0.9357 0.1335 -0.0878 0.180 Uiso 1 1 calc R
H41B H 1.0413 0.1200 0.0069 0.180 Uiso 1 1 calc R
H41C H 1.0273 0.2674 -0.0319 0.180 Uiso 1 1 calc R
C43 C 0.7228(8) 0.2671(6) -0.0039(3) 0.152(3) Uani 1 1 d .
H43A H 0.7728 0.3441 -0.0362 0.228 Uiso 1 1 calc R
H43B H 0.6632 0.3018 0.0478 0.228 Uiso 1 1 calc R
H43C H 0.6537 0.2075 -0.0501 0.228 Uiso 1 1 calc R
C44 C 0.8302(4) 0.1438(3) 0.1245(2) 0.0507(8) Uani 1 1 d .
H44 H 0.9133 0.0973 0.1456 0.061 Uiso 1 1 calc R
N42 N 0.8370(3) 0.1913(3) 0.03514(18) 0.0570(7) Uani 1 1 d .
O45 O 0.7293(3) 0.1547(3) 0.17968(19) 0.0779(8) 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'
F F 0.0171 0.0103 '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
C2 N1 C11 123.62(17) .
C2 N1 C6 114.03(17) .
C11 N1 C6 121.76(17) .
O2 C2 N1 126.3(2) .
O2 C2 C3 127.4(2) .
N1 C2 C3 106.34(17) .
C5 C3 C4 122.26(19) .
C5 C3 C2 108.55(18) .
C4 C3 C2 129.11(19) .
C5 C4 C3 115.7(2) 2_676
C4 C5 C3 122.0(2) 2_676
C4 C5 C6 127.77(19) 2_676
C3 C5 C6 110.23(18) .
O6 C6 N1 111.42(16) .
O6 C6 C5 112.70(16) .
N1 C6 C5 100.81(16) .
O6 C6 C21 108.72(17) .
N1 C6 C21 111.96(16) .
C5 C6 C21 111.12(17) .
C16 C11 C12 119.6(2) .
C16 C11 N1 121.05(19) .
C12 C11 N1 119.39(18) .
C13 C12 C11 119.9(2) .
C12 C13 C14 121.5(2) .
C15 C14 C13 117.9(2) .
C15 C14 C17 120.4(2) .
C13 C14 C17 121.7(2) .
C14 C15 C16 121.0(2) .
C11 C16 C15 120.0(2) .
C22 C21 C26 119.0(2) .
C22 C21 C6 120.31(19) .
C26 C21 C6 120.58(19) .
C21 C22 C23 120.7(2) .
C24 C23 C22 118.7(2) .
F27 C24 C25 118.3(2) .
F27 C24 C23 119.5(2) .
C25 C24 C23 122.2(2) .
C24 C25 C26 119.0(2) .
C21 C26 C25 120.4(2) .
C34 N32 C33 121.3(2) .
C34 N32 C31 122.1(2) .
C33 N32 C31 116.6(2) .
O35 C34 N32 124.8(2) .
O45 C44 N42 127.0(3) .
C44 N42 C43 122.3(3) .
C44 N42 C41 121.8(3) .
C43 N42 C41 115.7(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.372(3) .
N1 C11 1.444(3) .
N1 C6 1.496(3) .
C2 O2 1.232(2) .
C2 C3 1.501(3) .
C3 C5 1.399(3) .
C3 C4 1.400(3) .
C4 C5 1.395(3) 2_676
C5 C4 1.395(3) 2_676
C5 C6 1.531(3) .
C6 O6 1.397(3) .
C6 C21 1.528(3) .
C11 C16 1.380(3) .
C11 C12 1.392(3) .
C12 C13 1.392(3) .
C13 C14 1.392(3) .
C14 C15 1.389(3) .
C14 C17 1.524(3) .
C15 C16 1.407(3) .
C21 C22 1.386(3) .
C21 C26 1.394(3) .
C22 C23 1.394(3) .
C23 C24 1.369(4) .
C24 F27 1.366(3) .
C24 C25 1.371(4) .
C25 C26 1.390(3) .
C31 N32 1.464(3) .
N32 C34 1.315(3) .
N32 C33 1.461(3) .
C34 O35 1.258(3) .
C41 N42 1.465(5) .
C43 N42 1.395(5) .
C44 O45 1.187(4) .
C44 N42 1.338(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C11 N1 C2 O2 -6.7(3) . .
C6 N1 C2 O2 -177.99(19) . .
C11 N1 C2 C3 172.62(17) . .
C6 N1 C2 C3 1.3(2) . .
O2 C2 C3 C5 177.3(2) . .
N1 C2 C3 C5 -2.0(2) . .
O2 C2 C3 C4 0.6(3) . .
N1 C2 C3 C4 -178.7(2) . .
C5 C3 C4 C5 0.4(3) . 2_676
C2 C3 C4 C5 176.76(19) . 2_676
C4 C3 C5 C4 -0.5(3) . 2_676
C2 C3 C5 C4 -177.45(18) . 2_676
C4 C3 C5 C6 178.92(18) . .
C2 C3 C5 C6 1.9(2) . .
C2 N1 C6 O6 119.59(19) . .
C11 N1 C6 O6 -51.9(2) . .
C2 N1 C6 C5 -0.2(2) . .
C11 N1 C6 C5 -171.69(16) . .
C2 N1 C6 C21 -118.41(19) . .
C11 N1 C6 C21 70.1(2) . .
C4 C5 C6 O6 59.4(3) 2_676 .
C3 C5 C6 O6 -119.98(19) . .
C4 C5 C6 N1 178.23(19) 2_676 .
C3 C5 C6 N1 -1.1(2) . .
C4 C5 C6 C21 -63.0(3) 2_676 .
C3 C5 C6 C21 117.71(19) . .
C2 N1 C11 C16 91.7(3) . .
C6 N1 C11 C16 -97.7(2) . .
C2 N1 C11 C12 -89.1(3) . .
C6 N1 C11 C12 81.5(2) . .
C16 C11 C12 C13 -0.4(3) . .
N1 C11 C12 C13 -179.6(2) . .
C11 C12 C13 C14 0.9(4) . .
C12 C13 C14 C15 -0.6(4) . .
C12 C13 C14 C17 178.9(2) . .
C13 C14 C15 C16 -0.2(3) . .
C17 C14 C15 C16 -179.8(2) . .
C12 C11 C16 C15 -0.4(3) . .
N1 C11 C16 C15 178.79(19) . .
C14 C15 C16 C11 0.7(3) . .
O6 C6 C21 C22 162.45(18) . .
N1 C6 C21 C22 38.9(3) . .
C5 C6 C21 C22 -73.0(2) . .
O6 C6 C21 C26 -21.8(3) . .
N1 C6 C21 C26 -145.4(2) . .
C5 C6 C21 C26 102.8(2) . .
C26 C21 C22 C23 1.5(3) . .
C6 C21 C22 C23 177.2(2) . .
C21 C22 C23 C24 -1.0(4) . .
C22 C23 C24 F27 179.0(2) . .
C22 C23 C24 C25 0.0(4) . .
F27 C24 C25 C26 -178.4(2) . .
C23 C24 C25 C26 0.5(4) . .
C22 C21 C26 C25 -0.9(3) . .
C6 C21 C26 C25 -176.7(2) . .
C24 C25 C26 C21 -0.1(4) . .
C33 N32 C34 O35 2.7(4) . .
C31 N32 C34 O35 -178.7(2) . .
O45 C44 N42 C43 2.3(6) . .
O45 C44 N42 C41 177.2(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037803
