#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/31/1503105.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_1503105
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            'C11 H5 Cl F O2'
_chemical_formula_weight         223.60
_space_group_IT_number           14
_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                 98.5140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0998(2)
_cell_length_b                   6.05710(10)
_cell_length_c                   11.60960(10)
_cell_measurement_temperature    150(2)
_cell_volume                     911.03(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21542
_diffrn_reflns_theta_full        32.40
_diffrn_reflns_theta_max         32.40
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.439
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.439
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0308
_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)+(0.1414P)²+2.3547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2708
_reflns_number_total             3111
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol101338m_si_001.cif
_cod_data_source_block           466b
_cod_original_sg_symbol_H-M      'P 21 / c'
_cod_database_code               1503105
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
F1 F 0.96565(7) 0.79592(16) 0.93821(8) 0.0387(2) Uani 1 1 d
H12 H 0.7879(13) 0.918(3) 0.8446(15) 0.028(4) Uiso 1 1 d
H15 H 0.9957(16) 0.416(4) 0.8591(17) 0.042(5) Uiso 1 1 d
H13 H 0.6721(15) 0.722(3) 0.7079(16) 0.031(4) Uiso 1 1 d
H14 H 0.3555 0.2941 0.5348 0.050 Uiso 1 1 d
H11 H 0.8784 0.2220 0.7061 0.050 Uiso 1 1 d
Cl1 Cl 0.75626(2) 0.19039(5) 0.50583(2) 0.02604(9) Uani 1 1 d
O2 O 0.49315(7) -0.01308(14) 0.68246(7) 0.02307(17) Uani 1 1 d
O1 O 0.64787(6) 0.14365(13) 0.67620(7) 0.01917(16) Uani 1 1 d
C003 C 0.68999(8) 0.31999(16) 0.61452(9) 0.01645(18) Uani 1 1 d
C005 C 0.50927(8) 0.31993(15) 0.56922(8) 0.01501(17) Uani 1 1 d
C006 C 0.86127(8) 0.3618(2) 0.74314(10) 0.0218(2) Uani 1 1 d
C007 C 0.76528(7) 0.45186(17) 0.69832(8) 0.01627(18) Uani 1 1 d
C008 C 0.89986(9) 0.6825(2) 0.85912(10) 0.0248(2) Uani 1 1 d
C009 C 0.59660(7) 0.43704(16) 0.55085(8) 0.01501(17) Uani 1 1 d
C010 C 0.80612(9) 0.77748(19) 0.81647(10) 0.0226(2) Uani 1 1 d
C011 C 0.73787(8) 0.65863(18) 0.73597(9) 0.01922(19) Uani 1 1 d
C012 C 0.54205(8) 0.13211(17) 0.64711(8) 0.01700(18) Uani 1 1 d
C013 C 0.40968(8) 0.37728(17) 0.51948(8) 0.01615(17) Uani 1 1 d
C014 C 0.92915(9) 0.4764(2) 0.82477(11) 0.0261(2) 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'
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'
Cl Cl 0.1484 0.1585 '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
C012 O1 C003 111.16(8) . .
O1 C003 C007 109.52(8) . .
O1 C003 C009 104.44(8) . .
C007 C003 C009 118.20(8) . .
O1 C003 Cl1 106.45(6) . .
C007 C003 Cl1 110.10(7) . .
C009 C003 Cl1 107.43(7) . .
C013 C005 C009 123.51(9) . .
C013 C005 C012 128.07(9) . .
C009 C005 C012 108.41(8) . .
C014 C006 C007 120.63(11) . .
C011 C007 C006 119.60(10) . .
C011 C007 C003 120.34(9) . .
C006 C007 C003 119.98(9) . .
F1 C008 C010 118.47(11) . .
F1 C008 C014 118.63(11) . .
C010 C008 C014 122.90(11) . .
C005 C009 C013 121.79(9) . 3_666
C005 C009 C003 108.14(8) . .
C013 C009 C003 130.03(9) 3_666 .
C008 C010 C011 118.28(11) . .
C007 C011 C010 120.38(10) . .
O2 C012 O1 121.56(9) . .
O2 C012 C005 130.89(10) . .
O1 C012 C005 107.55(8) . .
C005 C013 C009 114.70(9) . 3_666
C006 C014 C008 118.19(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C008 1.3502(13) .
Cl1 C003 1.8128(10) .
O2 C012 1.1958(13) .
O1 C012 1.3791(12) .
O1 C003 1.4405(12) .
C003 C007 1.5077(14) .
C003 C009 1.5093(13) .
C005 C013 1.3903(13) .
C005 C009 1.3891(13) .
C005 C012 1.4770(14) .
C006 C014 1.3860(16) .
C006 C007 1.3985(14) .
C007 C011 1.3910(14) .
C008 C010 1.3797(17) .
C008 C014 1.3822(18) .
C009 C013 1.3851(13) 3_666
C010 C011 1.3941(15) .
C013 C009 1.3851(13) 3_666
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037802
