#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/20/48/7204850.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_7204850
loop_
_publ_author_name
'Li, Qi'
'Hu, Chunhua'
'Haerter, Roland'
'Englert, Ulli'
_publ_section_title
;
 Isosteric molecules in non-isomorphous structures: A new route to new
 structures. The example of 9,10-dihaloanthracene
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              83
_journal_paper_doi               10.1039/b401615g
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C14 H8 Cl2'
_chemical_formula_weight         247.10
_chemical_name_common            dichloroanthracene
_chemical_name_systematic
;
dichloroanthracene
;
_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                105.33(3)
_cell_angle_beta                 90.09(3)
_cell_angle_gamma                100.97(3)
_cell_formula_units_Z            2
_cell_length_a                   3.9004(8)
_cell_length_b                   8.7632(18)
_cell_length_c                   16.508(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      35
_cell_measurement_theta_min      17
_cell_volume                     533.4(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0965
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3789
_diffrn_reflns_theta_full        73.92
_diffrn_reflns_theta_max         73.92
_diffrn_reflns_theta_min         5.31
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  166
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.153
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2140
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1147P)²+0.0684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1557
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                1657
_reflns_number_total             2140
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b401615g.txt
_cod_data_source_block           3b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+0.0684P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1147P)^2^+0.0684P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        533.42(19)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204850
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3108(2) 0.28774(10) 0.15710(5) 0.0520(3) Uani 1 d . . .
C9 C 0.1359(8) 0.1261(4) 0.0689(2) 0.0415(7) Uani 1 d . . .
C9A C 0.2296(8) 0.1395(4) -0.01091(19) 0.0407(6) Uani 1 d . . .
C1 C 0.4606(9) 0.2761(4) -0.0248(2) 0.0511(8) Uani 1 d . . .
H1A H 0.5564 0.3616 0.0209 0.061 Uiso 1 calc R . .
C2 C 0.5431(11) 0.2833(5) -0.1038(3) 0.0581(9) Uani 1 d . . .
H2A H 0.6939 0.3735 -0.1115 0.070 Uiso 1 calc R . .
C3 C 0.4011(10) 0.1543(5) -0.1744(2) 0.0577(9) Uani 1 d . . .
H3A H 0.4585 0.1606 -0.2282 0.069 Uiso 1 calc R . .
C4 C 0.1847(9) 0.0234(4) -0.1640(2) 0.0497(8) Uani 1 d . . .
H4A H 0.0939 -0.0599 -0.2112 0.060 Uiso 1 calc R . .
C4A C 0.0892(8) 0.0082(4) -0.08245(19) 0.0415(7) Uani 1 d . . .
Cl2 Cl 0.4359(2) 0.83802(9) 0.61821(5) 0.0527(3) Uani 1 d . . .
C9B C 0.4709(7) 0.6484(3) 0.55194(19) 0.0378(6) Uani 1 d . . .
C9AB C 0.3461(7) 0.5117(4) 0.57900(19) 0.0374(6) Uani 1 d . . .
C1B C 0.1866(8) 0.5156(4) 0.65705(19) 0.0453(7) Uani 1 d . . .
H1B H 0.1611 0.6144 0.6923 0.054 Uiso 1 calc R . .
C2B C 0.0723(10) 0.3807(5) 0.6812(2) 0.0536(8) Uani 1 d . . .
H2BA H -0.0263 0.3875 0.7329 0.064 Uiso 1 calc R . .
C3B C 0.1013(10) 0.2284(5) 0.6282(2) 0.0536(8) Uani 1 d . . .
H3BA H 0.0191 0.1354 0.6450 0.064 Uiso 1 calc R . .
C4B C 0.2479(8) 0.2173(4) 0.5533(2) 0.0463(7) Uani 1 d . . .
H4BA H 0.2658 0.1162 0.5193 0.056 Uiso 1 calc R . .
C4AB C 0.3757(7) 0.3571(3) 0.52528(18) 0.0377(6) Uani 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0492(5) 0.0540(5) 0.0444(4) -0.0010(3) 0.0001(3) 0.0099(3)
C9 0.0324(14) 0.0462(16) 0.0447(16) 0.0042(12) -0.0007(11) 0.0164(11)
C9A 0.0331(14) 0.0462(16) 0.0449(16) 0.0103(12) 0.0045(11) 0.0158(11)
C1 0.0416(17) 0.0493(18) 0.063(2) 0.0138(15) 0.0065(15) 0.0132(14)
C2 0.050(2) 0.060(2) 0.073(2) 0.0280(19) 0.0158(17) 0.0148(16)
C3 0.052(2) 0.078(3) 0.055(2) 0.0313(19) 0.0179(16) 0.0242(18)
C4 0.0479(19) 0.062(2) 0.0426(17) 0.0125(14) 0.0074(13) 0.0215(15)
C4A 0.0368(15) 0.0504(17) 0.0409(15) 0.0105(13) 0.0035(11) 0.0202(12)
Cl2 0.0531(5) 0.0402(4) 0.0580(5) 0.0003(3) 0.0112(4) 0.0108(3)
C9B 0.0273(13) 0.0381(14) 0.0442(15) 0.0036(11) -0.0015(11) 0.0077(10)
C9AB 0.0252(13) 0.0440(15) 0.0405(14) 0.0065(11) 0.0003(10) 0.0079(10)
C1B 0.0349(15) 0.0574(19) 0.0399(16) 0.0066(13) 0.0035(12) 0.0096(13)
C2B 0.0428(18) 0.074(2) 0.0467(18) 0.0232(17) 0.0069(14) 0.0088(16)
C3B 0.0422(18) 0.057(2) 0.064(2) 0.0272(17) 0.0004(15) 0.0003(14)
C4B 0.0367(16) 0.0454(17) 0.0562(19) 0.0147(14) -0.0008(13) 0.0048(12)
C4AB 0.0255(13) 0.0425(15) 0.0426(15) 0.0074(12) -0.0005(10) 0.0060(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
C4A C9 C9A 123.3(3) 2 . ?
C4A C9 Cl1 118.5(2) 2 . ?
C9A C9 Cl1 118.2(3) . . ?
C1 C9A C9 123.4(3) . . ?
C1 C9A C4A 118.4(3) . . ?
C9 C9A C4A 118.2(3) . . ?
C2 C1 C9A 121.1(3) . . ?
C2 C1 H1A 119.5 . . ?
C9A C1 H1A 119.5 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
C3 C4 C4A 121.9(3) . . ?
C3 C4 H4A 119.1 . . ?
C4A C4 H4A 119.1 . . ?
C9 C4A C9A 118.5(3) 2 . ?
C9 C4A C4 123.7(3) 2 . ?
C9A C4A C4 117.8(3) . . ?
C9AB C9B C4AB 123.3(3) . 2_666 ?
C9AB C9B Cl2 118.3(2) . . ?
C4AB C9B Cl2 118.4(2) 2_666 . ?
C9B C9AB C4AB 118.4(3) . . ?
C9B C9AB C1B 123.8(3) . . ?
C4AB C9AB C1B 117.7(3) . . ?
C2B C1B C9AB 122.0(3) . . ?
C2B C1B H1B 119.0 . . ?
C9AB C1B H1B 119.0 . . ?
C1B C2B C3B 120.3(3) . . ?
C1B C2B H2BA 119.9 . . ?
C3B C2B H2BA 119.9 . . ?
C4B C3B C2B 120.4(3) . . ?
C4B C3B H3BA 119.8 . . ?
C2B C3B H3BA 119.8 . . ?
C3B C4B C4AB 121.4(3) . . ?
C3B C4B H4BA 119.3 . . ?
C4AB C4B H4BA 119.3 . . ?
C9B C4AB C4B 123.5(3) 2_666 . ?
C9B C4AB C9AB 118.3(3) 2_666 . ?
C4B C4AB C9AB 118.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.769(3) . ?
C9 C4A 1.397(5) 2 ?
C9 C9A 1.397(4) . ?
C9A C1 1.425(5) . ?
C9A C4A 1.435(4) . ?
C1 C2 1.357(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.416(6) . ?
C2 H2A 0.9300 . ?
C3 C4 1.339(5) . ?
C3 H3A 0.9300 . ?
C4 C4A 1.431(5) . ?
C4 H4A 0.9300 . ?
C4A C9 1.397(5) 2 ?
Cl2 C9B 1.761(3) . ?
C9B C9AB 1.390(4) . ?
C9B C4AB 1.402(4) 2_666 ?
C9AB C4AB 1.436(4) . ?
C9AB C1B 1.427(4) . ?
C1B C2B 1.342(5) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.414(6) . ?
C2B H2BA 0.9300 . ?
C3B C4B 1.351(5) . ?
C3B H3BA 0.9300 . ?
C4B C4AB 1.425(4) . ?
C4B H4BA 0.9300 . ?
C4AB C9B 1.402(4) 2_666 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15196007
