#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503203.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_1503203
loop_
_publ_author_name
'Huo, Fang-Jun'
'Sun, Yuan-Qiang'
'Su, Jing'
'Yang, Yu-Tao'
'Yin, Cai-Xia'
'Chao, Jian-Bin'
_publ_section_title
;
 Chromene "lock", thiol "key", and mercury(II) ion
 "hand": a single molecular machine recognition system.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              4756
_journal_page_last               4759
_journal_paper_doi               10.1021/ol101771j
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C12 H9 Cl O2'
_chemical_formula_weight         220.64
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.103(3)
_cell_length_b                   6.0078(12)
_cell_length_c                   21.747(4)
_cell_measurement_temperature    571(2)
_cell_volume                     1973.2(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7515
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.0127(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0442
_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)+(0.0353P)²+1.7818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1575
_reflns_number_total             1766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101771j_si_002.cif
_cod_data_source_block           hfj2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        1973.3(7)
_cod_database_code               1503203
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Cl1 Cl 0.33141(4) 1.01725(10) 0.71629(3) 0.0358(2) Uani 1 1 d .
O1 O 0.42997(11) 0.7297(3) 0.46747(7) 0.0337(4) Uani 1 1 d .
O2 O 0.31808(11) 1.3336(3) 0.35072(8) 0.0373(4) Uani 1 1 d .
C6 C 0.33975(14) 1.1368(4) 0.47946(10) 0.0266(5) Uani 1 1 d .
H6A H 0.3210 1.2835 0.4837 0.032 Uiso 1 1 calc R
C12 C 0.40042(15) 0.7958(4) 0.52431(10) 0.0263(5) Uani 1 1 d .
C8 C 0.33299(14) 1.0625(4) 0.59261(10) 0.0261(5) Uani 1 1 d .
H8A H 0.3030 1.1957 0.5992 0.031 Uiso 1 1 calc R
C4 C 0.43048(16) 0.8040(4) 0.35653(10) 0.0313(5) Uani 1 1 d .
H4A H 0.4252 0.6602 0.3366 0.038 Uiso 1 1 calc R
H4B H 0.4926 0.8351 0.3638 0.038 Uiso 1 1 calc R
C11 C 0.42229(16) 0.6624(4) 0.57410(11) 0.0333(6) Uani 1 1 d .
H11A H 0.4526 0.5295 0.5680 0.040 Uiso 1 1 calc R
C2 C 0.35284(14) 1.0473(4) 0.42397(11) 0.0272(5) Uani 1 1 d .
C1 C 0.34879(14) 1.1515(4) 0.36244(10) 0.0277(5) Uani 1 1 d .
C9 C 0.35504(14) 0.9285(4) 0.64194(10) 0.0273(5) Uani 1 1 d .
C3 C 0.37876(16) 0.8075(4) 0.41655(11) 0.0327(6) Uani 1 1 d .
H3A H 0.3254 0.7160 0.4123 0.039 Uiso 1 1 calc R
C7 C 0.35566(14) 0.9980(3) 0.53282(10) 0.0246(5) Uani 1 1 d .
C10 C 0.39871(15) 0.7280(4) 0.63317(10) 0.0313(5) Uani 1 1 d .
H10A H 0.4122 0.6379 0.6666 0.038 Uiso 1 1 calc R
C5 C 0.38833(16) 0.9870(4) 0.31714(11) 0.0320(6) Uani 1 1 d .
H5A H 0.4326 1.0588 0.2916 0.038 Uiso 1 1 calc R
H5B H 0.3427 0.9255 0.2908 0.038 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C12 O1 C3 115.27(17)
C2 C6 C7 117.9(2)
C2 C6 H6A 121.1
C7 C6 H6A 121.1
O1 C12 C11 117.3(2)
O1 C12 C7 121.75(19)
C11 C12 C7 120.8(2)
C9 C8 C7 120.1(2)
C9 C8 H8A 120.0
C7 C8 H8A 120.0
C3 C4 C5 104.85(19)
C3 C4 H4A 110.8
C5 C4 H4A 110.8
C3 C4 H4B 110.8
C5 C4 H4B 110.8
H4A C4 H4B 108.9
C12 C11 C10 119.8(2)
C12 C11 H11A 120.1
C10 C11 H11A 120.1
C6 C2 C1 129.9(2)
C6 C2 C3 121.5(2)
C1 C2 C3 108.64(19)
O2 C1 C2 125.9(2)
O2 C1 C5 126.9(2)
C2 C1 C5 107.18(19)
C8 C9 C10 120.9(2)
C8 C9 Cl1 119.59(18)
C10 C9 Cl1 119.45(18)
O1 C3 C2 111.82(19)
O1 C3 C4 112.48(19)
C2 C3 C4 103.86(19)
O1 C3 H3A 109.5
C2 C3 H3A 109.5
C4 C3 H3A 109.5
C8 C7 C12 118.7(2)
C8 C7 C6 123.0(2)
C12 C7 C6 118.2(2)
C9 C10 C11 119.7(2)
C9 C10 H10A 120.1
C11 C10 H10A 120.1
C1 C5 C4 105.54(19)
C1 C5 H5A 110.6
C4 C5 H5A 110.6
C1 C5 H5B 110.6
C4 C5 H5B 110.6
H5A C5 H5B 108.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.739(2)
O1 C12 1.373(2)
O1 C3 1.429(3)
O2 C1 1.215(3)
C6 C2 1.336(3)
C6 C7 1.449(3)
C6 H6A 0.9300
C12 C11 1.387(3)
C12 C7 1.402(3)
C8 C9 1.382(3)
C8 C7 1.399(3)
C8 H8A 0.9300
C4 C3 1.521(3)
C4 C5 1.532(3)
C4 H4A 0.9700
C4 H4B 0.9700
C11 C10 1.390(3)
C11 H11A 0.9300
C2 C1 1.479(3)
C2 C3 1.502(3)
C1 C5 1.518(3)
C9 C10 1.387(3)
C3 H3A 0.9800
C10 H10A 0.9300
C5 H5A 0.9700
C5 H5B 0.9700
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
C3 O1 C12 C11 154.8(2)
C3 O1 C12 C7 -29.9(3)
O1 C12 C11 C10 176.2(2)
C7 C12 C11 C10 0.8(4)
C7 C6 C2 C1 -174.7(2)
C7 C6 C2 C3 3.0(3)
C6 C2 C1 O2 -13.1(4)
C3 C2 C1 O2 168.9(2)
C6 C2 C1 C5 168.0(2)
C3 C2 C1 C5 -10.0(2)
C7 C8 C9 C10 -0.8(3)
C7 C8 C9 Cl1 176.79(16)
C12 O1 C3 C2 42.6(3)
C12 O1 C3 C4 159.02(19)
C6 C2 C3 O1 -30.5(3)
C1 C2 C3 O1 147.66(19)
C6 C2 C3 C4 -152.1(2)
C1 C2 C3 C4 26.1(2)
C5 C4 C3 O1 -152.84(19)
C5 C4 C3 C2 -31.7(2)
C9 C8 C7 C12 0.3(3)
C9 C8 C7 C6 -175.9(2)
O1 C12 C7 C8 -175.5(2)
C11 C12 C7 C8 -0.3(3)
O1 C12 C7 C6 0.9(3)
C11 C12 C7 C6 176.1(2)
C2 C6 C7 C8 -171.1(2)
C2 C6 C7 C12 12.7(3)
C8 C9 C10 C11 1.3(3)
Cl1 C9 C10 C11 -176.32(19)
C12 C11 C10 C9 -1.3(4)
O2 C1 C5 C4 170.9(2)
C2 C1 C5 C4 -10.2(2)
C3 C4 C5 C1 26.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037867
