#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/32/7203202.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_7203202
loop_
_publ_author_name
'Zeng, Qingdao'
'Wu, Dongxia'
'Ma, Hongwei'
'Shu, Chuying'
'Li, Yan'
'Wang, Chen'
_publ_section_title
;
 Polymeric hydrogen-bonded supramolecules by self-assembling of
 adamantane derivatives with bipyridines
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              189
_journal_paper_doi               10.1039/b516212b
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C22 H24 N2 O4 S2'
_chemical_formula_weight         444.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 113.90(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.764(2)
_cell_length_b                   15.841(3)
_cell_length_c                   12.322(3)
_cell_measurement_reflns_used    18372
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.02
_cell_volume                     2099.4(9)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       'ω oscillation'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18372
_diffrn_reflns_theta_full        27.33
_diffrn_reflns_theta_max         27.33
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.8352
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   Abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0406
_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)+(0.0709P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1115
_reflns_number_gt                3754
_reflns_number_total             4711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b516212b.txt
_cod_data_source_block           compound_6
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
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:

'_symmetry_cell_setting' tag value 'Monclinic' was replaced with
'monoclinic' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2099.5(7)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7203202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.51693(4) 0.19360(3) 0.11210(4) 0.04439(13) Uani 1 1 d . . .
S2 S 0.63501(4) 0.29100(3) 0.12801(3) 0.04622(13) Uani 1 1 d . . .
O1 O -0.07231(12) 0.05319(8) -0.13855(12) 0.0593(4) Uani 1 1 d . . .
O2 O 0.12256(11) 0.06890(8) -0.11892(11) 0.0526(3) Uani 1 1 d . . .
H2A H 0.1002 0.0355 -0.1745 0.063 Uiso 1 1 calc R . .
O3 O -0.03957(11) 0.41829(8) -0.15084(11) 0.0565(3) Uani 1 1 d . . .
H3C H -0.0349 0.4550 -0.1958 0.068 Uiso 1 1 calc R . .
O4 O 0.16472(12) 0.43344(9) -0.07044(13) 0.0681(4) Uani 1 1 d . . .
N1 N 0.53864(13) 0.02764(8) -0.18137(11) 0.0427(3) Uani 1 1 d . . .
N2 N 0.44955(15) 0.46226(9) -0.19336(13) 0.0501(3) Uani 1 1 d . . .
C1 C 0.02670(14) 0.08876(9) -0.09378(13) 0.0359(3) Uani 1 1 d . . .
C2 C 0.05218(12) 0.16247(9) -0.00830(11) 0.0299(3) Uani 1 1 d . . .
C3 C -0.05302(14) 0.17014(10) 0.03453(13) 0.0356(3) Uani 1 1 d . . .
H3A H -0.1321 0.1754 -0.0333 0.043 Uiso 1 1 calc R . .
H3B H -0.0557 0.1196 0.0779 0.043 Uiso 1 1 calc R . .
C4 C -0.03203(15) 0.24749(10) 0.11491(14) 0.0401(4) Uani 1 1 d . . .
H4A H -0.0993 0.2512 0.1424 0.048 Uiso 1 1 calc R . .
C5 C -0.03260(15) 0.32697(10) 0.04419(14) 0.0382(3) Uani 1 1 d . . .
H5A H -0.0220 0.3765 0.0936 0.046 Uiso 1 1 calc R . .
H5B H -0.1117 0.3318 -0.0237 0.046 Uiso 1 1 calc R . .
C6 C 0.07374(13) 0.32204(9) 0.00180(12) 0.0316(3) Uani 1 1 d . . .
C7 C 0.19845(14) 0.31303(10) 0.11006(13) 0.0394(3) Uani 1 1 d . . .
H7A H 0.2658 0.3098 0.0840 0.047 Uiso 1 1 calc R . .
H7B H 0.2122 0.3620 0.1611 0.047 Uiso 1 1 calc R . .
C8 C 0.19673(15) 0.23294(10) 0.17926(13) 0.0415(4) Uani 1 1 d . . .
H8A H 0.2763 0.2278 0.2482 0.050 Uiso 1 1 calc R . .
C9 C 0.17690(13) 0.15446(10) 0.10042(13) 0.0380(3) Uani 1 1 d . . .
H9A H 0.1764 0.1042 0.1452 0.046 Uiso 1 1 calc R . .
H9B H 0.2443 0.1494 0.0746 0.046 Uiso 1 1 calc R . .
C10 C 0.05539(12) 0.24312(8) -0.07730(12) 0.0297(3) Uani 1 1 d . . .
H10A H -0.0219 0.2482 -0.1472 0.036 Uiso 1 1 calc R . .
H10B H 0.1229 0.2392 -0.1032 0.036 Uiso 1 1 calc R . .
C11 C 0.09204(17) 0.23859(12) 0.22199(14) 0.0489(4) Uani 1 1 d . . .
H11A H 0.1052 0.2869 0.2740 0.059 Uiso 1 1 calc R . .
H11B H 0.0913 0.1882 0.2663 0.059 Uiso 1 1 calc R . .
C12 C 0.07291(14) 0.39785(9) -0.07457(13) 0.0381(3) Uani 1 1 d . . .
C13 C 0.43071(16) 0.04800(11) -0.17646(15) 0.0483(4) Uani 1 1 d . . .
H13A H 0.3580 0.0268 -0.2350 0.058 Uiso 1 1 calc R . .
C14 C 0.42075(15) 0.09864(11) -0.08962(15) 0.0435(4) Uani 1 1 d . . .
H14A H 0.3436 0.1108 -0.0893 0.052 Uiso 1 1 calc R . .
C15 C 0.52878(14) 0.13078(9) -0.00302(12) 0.0341(3) Uani 1 1 d . . .
C16 C 0.64174(14) 0.10974(10) -0.00611(13) 0.0385(3) Uani 1 1 d . . .
H16A H 0.7159 0.1299 0.0515 0.046 Uiso 1 1 calc R . .
C17 C 0.64224(15) 0.05839(10) -0.09625(14) 0.0412(3) Uani 1 1 d . . .
H17A H 0.7183 0.0445 -0.0979 0.049 Uiso 1 1 calc R . .
C18 C 0.38461(16) 0.40124(11) -0.17059(15) 0.0468(4) Uani 1 1 d . . .
H18A H 0.3014 0.3950 -0.2218 0.056 Uiso 1 1 calc R . .
C19 C 0.43346(15) 0.34649(11) -0.07528(14) 0.0420(4) Uani 1 1 d . . .
H19A H 0.3844 0.3045 -0.0635 0.050 Uiso 1 1 calc R . .
C20 C 0.55660(14) 0.35556(9) 0.00210(12) 0.0364(3) Uani 1 1 d . . .
C21 C 0.62529(17) 0.41962(11) -0.01867(15) 0.0466(4) Uani 1 1 d . . .
H21A H 0.7080 0.4282 0.0323 0.056 Uiso 1 1 calc R . .
C22 C 0.56798(19) 0.47068(11) -0.11706(16) 0.0536(5) Uani 1 1 d . . .
H22A H 0.6148 0.5134 -0.1308 0.064 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'
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'
S S 0.1246 0.1234 '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
C15 S1 S2 103.28(5) . . ?
C20 S2 S1 105.10(6) . . ?
C13 N1 C17 117.25(14) . . ?
C18 N2 C22 116.66(15) . . ?
O1 C1 O2 122.56(14) . . ?
O1 C1 C2 123.95(14) . . ?
O2 C1 C2 113.44(12) . . ?
C1 C2 C3 109.84(11) . . ?
C1 C2 C9 113.01(12) . . ?
C3 C2 C9 108.92(11) . . ?
C1 C2 C10 107.24(11) . . ?
C3 C2 C10 109.09(11) . . ?
C9 C2 C10 108.67(11) . . ?
C4 C3 C2 110.16(12) . . ?
C11 C4 C5 110.51(13) . . ?
C11 C4 C3 109.40(13) . . ?
C5 C4 C3 109.13(12) . . ?
C4 C5 C6 109.55(12) . . ?
C12 C6 C5 111.51(12) . . ?
C12 C6 C7 111.96(12) . . ?
C5 C6 C7 109.32(12) . . ?
C12 C6 C10 106.49(11) . . ?
C5 C6 C10 109.25(12) . . ?
C7 C6 C10 108.20(12) . . ?
C8 C7 C6 109.64(12) . . ?
C11 C8 C7 109.74(14) . . ?
C11 C8 C9 109.19(13) . . ?
C7 C8 C9 110.53(13) . . ?
C8 C9 C2 109.30(12) . . ?
C2 C10 C6 110.52(11) . . ?
C8 C11 C4 109.27(12) . . ?
O4 C12 O3 122.79(15) . . ?
O4 C12 C6 124.29(15) . . ?
O3 C12 C6 112.84(13) . . ?
N1 C13 C14 123.83(15) . . ?
C13 C14 C15 118.17(15) . . ?
C14 C15 C16 118.81(14) . . ?
C14 C15 S1 118.38(12) . . ?
C16 C15 S1 122.74(12) . . ?
C17 C16 C15 118.77(14) . . ?
N1 C17 C16 123.17(15) . . ?
N2 C18 C19 123.90(16) . . ?
C20 C19 C18 118.65(15) . . ?
C19 C20 C21 118.43(15) . . ?
C19 C20 S2 124.90(12) . . ?
C21 C20 S2 116.67(12) . . ?
C22 C21 C20 118.46(16) . . ?
N2 C22 C21 123.89(16) . . ?
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
S1 C15 1.7839(15) . ?
S1 S2 2.0318(7) . ?
S2 C20 1.7733(16) . ?
O1 C1 1.2074(19) . ?
O2 C1 1.3228(19) . ?
O3 C12 1.316(2) . ?
O4 C12 1.2011(19) . ?
N1 C13 1.335(2) . ?
N1 C17 1.337(2) . ?
N2 C18 1.331(2) . ?
N2 C22 1.335(3) . ?
C1 C2 1.519(2) . ?
C2 C3 1.534(2) . ?
C2 C9 1.540(2) . ?
C2 C10 1.5436(19) . ?
C3 C4 1.531(2) . ?
C4 C11 1.527(2) . ?
C4 C5 1.530(2) . ?
C5 C6 1.541(2) . ?
C6 C12 1.523(2) . ?
C6 C7 1.538(2) . ?
C6 C10 1.5457(19) . ?
C7 C8 1.533(2) . ?
C8 C11 1.526(3) . ?
C8 C9 1.536(2) . ?
C13 C14 1.380(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.379(2) . ?
C18 C19 1.384(2) . ?
C19 C20 1.382(2) . ?
C20 C21 1.384(2) . ?
C21 C22 1.384(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N2 0.82 1.89 2.7082(19) 177.4 2_544
O3 H3C N1 0.82 1.89 2.7006(18) 170.9 2_554
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195045
