#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/57/4125710.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_4125710
loop_
_publ_author_name
'Saha, Subhankar'
'Desiraju, Gautam R.'
_publ_section_title
;
 Crystal Engineering of Hand-Twisted Helical Crystals.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1975
_journal_page_last               1983
_journal_paper_doi               10.1021/jacs.6b11835
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C13 H8 Cl I O2'
_chemical_formula_weight         358.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 97.57(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.896(8)
_cell_length_b                   11.086(6)
_cell_length_c                   7.596(4)
_cell_measurement_reflns_used    4535
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.8
_cell_measurement_theta_min      2.3
_cell_volume                     1243.4(12)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.379
_exptl_absorpt_coefficient_mu    2.775
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.214
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.198
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0705P)²+1.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2306
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b11835_si_004.cif
_cod_data_source_block           B1
_cod_original_cell_volume        1243.5(10)
_cod_database_code               4125710
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.650
_shelx_estimated_absorpt_t_max   0.681
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C3 C 0.0626(3) 0.1383(3) -0.2526(5) 0.0210(7) Uani 1 1 d . .
C4 C 0.2171(3) 0.2049(3) -0.1817(6) 0.0259(8) Uani 1 1 d . .
H4 H 0.2626 0.2641 -0.1881 0.031 Uiso 1 1 calc R U
C5 C 0.0840(3) 0.0305(4) -0.1617(6) 0.0241(8) Uani 1 1 d . .
H5 H 0.0383 -0.0286 -0.1558 0.029 Uiso 1 1 calc R U
C6 C -0.1816(3) 0.1034(4) -0.3586(5) 0.0224(8) Uani 1 1 d . .
C7 C 0.1709(3) 0.0090(3) -0.0804(6) 0.0250(8) Uani 1 1 d . .
H7 H 0.1855 -0.0643 -0.0185 0.030 Uiso 1 1 calc R U
C8 C -0.2269(3) 0.0179(3) -0.4688(5) 0.0246(8) Uani 1 1 d . .
H8 H -0.1955 -0.0506 -0.5045 0.030 Uiso 1 1 calc R U
C9 C 0.2370(3) 0.0967(4) -0.0907(6) 0.0240(8) Uani 1 1 d . .
C10 C 0.1289(3) 0.2240(3) -0.2626(6) 0.0256(8) Uani 1 1 d . .
H10 H 0.1142 0.2969 -0.3256 0.031 Uiso 1 1 calc R U
C11 C -0.2261(3) 0.2034(4) -0.3030(6) 0.0261(8) Uani 1 1 d . .
H11 H -0.1944 0.2608 -0.2253 0.031 Uiso 1 1 calc R U
C12 C -0.0298(3) 0.1646(3) -0.3410(5) 0.0245(8) Uani 1 1 d . .
C13 C -0.3618(3) 0.1337(4) -0.4739(6) 0.0276(9) Uani 1 1 d . .
C14 C -0.3170(3) 0.2184(4) -0.3618(6) 0.0283(9) Uani 1 1 d . .
H14 H -0.3485 0.2866 -0.3254 0.034 Uiso 1 1 calc R U
C15 C -0.3181(3) 0.0326(4) -0.5268(6) 0.0276(8) Uani 1 1 d . .
H15 H -0.3503 -0.0259 -0.6019 0.033 Uiso 1 1 calc R U
O1 O -0.0901(2) 0.0824(2) -0.2967(5) 0.0257(7) Uani 1 1 d . .
O2 O -0.0500(2) 0.2482(3) -0.4386(5) 0.0338(7) Uani 1 1 d . .
Cl1 Cl -0.47527(8) 0.15639(12) -0.55253(19) 0.0446(3) Uani 1 1 d . .
I1 I 0.36854(2) 0.06789(3) 0.03819(4) 0.03474(19) 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C10 C3 C5 119.9(4)
C10 C3 C12 118.0(3)
C5 C3 C12 122.1(3)
C10 C4 C9 118.5(4)
C10 C4 H4 120.8
C9 C4 H4 120.8
C7 C5 C3 120.6(4)
C7 C5 H5 119.7
C3 C5 H5 119.7
C8 C6 C11 121.2(4)
C8 C6 O1 117.7(4)
C11 C6 O1 120.9(4)
C5 C7 C9 118.9(4)
C5 C7 H7 120.6
C9 C7 H7 120.6
C6 C8 C15 119.6(4)
C6 C8 H8 120.2
C15 C8 H8 120.2
C7 C9 C4 121.4(4)
C7 C9 I1 119.4(3)
C4 C9 I1 119.1(3)
C3 C10 C4 120.8(4)
C3 C10 H10 119.6
C4 C10 H10 119.6
C14 C11 C6 119.1(4)
C14 C11 H11 120.4
C6 C11 H11 120.4
O2 C12 O1 123.6(4)
O2 C12 C3 125.1(4)
O1 C12 C3 111.3(3)
C14 C13 C15 121.6(4)
C14 C13 Cl1 119.0(3)
C15 C13 Cl1 119.4(3)
C11 C14 C13 119.5(4)
C11 C14 H14 120.2
C13 C14 H14 120.2
C13 C15 C8 118.9(4)
C13 C15 H15 120.6
C8 C15 H15 120.6
C12 O1 C6 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C3 C10 1.380(6)
C3 C5 1.395(5)
C3 C12 1.479(5)
C4 C10 1.391(6)
C4 C9 1.396(6)
C4 H4 0.9500
C5 C7 1.380(6)
C5 H5 0.9500
C6 C8 1.380(6)
C6 C11 1.386(6)
C6 O1 1.401(5)
C7 C9 1.393(6)
C7 H7 0.9500
C8 C15 1.383(6)
C8 H8 0.9500
C9 I1 2.097(4)
C10 H10 0.9500
C11 C14 1.379(6)
C11 H11 0.9500
C12 O2 1.200(5)
C12 O1 1.352(5)
C13 C14 1.379(6)
C13 C15 1.383(6)
C13 Cl1 1.735(4)
C14 H14 0.9500
C15 H15 0.9500
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
C10 C3 C5 C7 0.5(6)
C12 C3 C5 C7 -179.9(4)
C3 C5 C7 C9 0.0(6)
C11 C6 C8 C15 0.8(6)
O1 C6 C8 C15 177.3(4)
C5 C7 C9 C4 -0.2(6)
C5 C7 C9 I1 178.2(3)
C10 C4 C9 C7 0.1(6)
C10 C4 C9 I1 -178.4(3)
C5 C3 C10 C4 -0.6(6)
C12 C3 C10 C4 179.7(4)
C9 C4 C10 C3 0.3(6)
C8 C6 C11 C14 -1.2(6)
O1 C6 C11 C14 -177.6(4)
C10 C3 C12 O2 9.2(6)
C5 C3 C12 O2 -170.4(4)
C10 C3 C12 O1 -170.2(4)
C5 C3 C12 O1 10.1(5)
C6 C11 C14 C13 0.3(6)
C15 C13 C14 C11 1.1(7)
Cl1 C13 C14 C11 -177.9(3)
C14 C13 C15 C8 -1.5(7)
Cl1 C13 C15 C8 177.5(3)
C6 C8 C15 C13 0.5(6)
O2 C12 O1 C6 -5.2(6)
C3 C12 O1 C6 174.3(3)
C8 C6 O1 C12 119.5(4)
C11 C6 O1 C12 -64.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125133
