#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:38:18 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133759.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_7133759
loop_
_publ_author_name
'Dillon, Alexandra M.'
'Shtukenberg, Alexander G.'
'Demkiw, Krystyna M.'
'Woerpel, K. A.'
'Ward, Michael D.'
_publ_section_title
;
 Hydrogen-bonded frameworks for conformational analysis of reactive
 substrates.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11770
_journal_page_last               11773
_journal_paper_doi               10.1039/d4cc03430a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C21 H27 Cl N6 O7 S2'
_chemical_formula_weight         575.05
_chemical_name_systematic
'guanidinium 1,5-naphthalenedisulfonate 2-chloropropiophenone'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-06-20 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.117(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.6588(5)
_cell_length_b                   20.9928(11)
_cell_length_c                   8.0310(5)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.72
_cell_volume                     1291.22(13)
_computing_cell_refinement       'Bruker APEX4'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker APEX4'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      100.(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12933
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              Incoatec
_exptl_absorpt_coefficient_mu    0.363
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol ethanol'
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.110
_refine_diff_density_max         1.474
_refine_diff_density_min         -0.936
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     240
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.1700
_refine_ls_R_factor_gt           0.1588
_refine_ls_shift/su_max          0.100
_refine_ls_shift/su_mean         0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1832P)²+6.9779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3972
_refine_ls_wR_factor_ref         0.4046
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2767
_reflns_number_total             3239
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03430a2.cif
_cod_data_source_block           24mdw38d
_cod_depositor_comments
'Adding full bibliography for 7133757--7133764.cif.'
_cod_database_code               7133759
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.5000(7) 0.7090(2) 0.4113(7) 0.0510(12) Uani d . . . 1.000000 . .
O O2 0.3437(7) 0.6392(2) 0.2241(6) 0.0499(12) Uani d . . . 1.000000 . .
O O3 0.6573(7) 0.6391(2) 0.2230(6) 0.0484(12) Uani d . . . 1.000000 . .
S S1 0.4996(2) 0.64843(6) 0.3234(2) 0.0434(5) Uani d . . . 1.000000 . .
C C5 0.5003(11) 0.5885(3) 0.4797(8) 0.0482(16) Uani d U . D 1.000000 . .
C C1 0.4999(10) 0.4773(3) 0.5662(7) 0.0461(16) Uani d U . D 1.000000 . .
C C4A 0.541(4) 0.6071(8) 0.6383(16) 0.047(5) Uani d U P D 0.49(3) A 1
H H4A 0.562833 0.650768 0.661907 0.057000 Uiso calc U P R 0.49(3) A 1
C C3A 0.551(4) 0.5615(7) 0.7667(16) 0.046(4) Uani d U P D 0.49(3) A 1
H H3A 0.566269 0.574981 0.878690 0.056000 Uiso calc U P R 0.49(3) A 1
C C2A 0.539(3) 0.4982(7) 0.7312(17) 0.042(4) Uani d U P D 0.49(3) A 1
H H2A 0.556960 0.467728 0.817007 0.051000 Uiso calc U P R 0.49(3) A 1
C C4B 0.462(4) 0.6072(7) 0.6388(16) 0.049(5) Uani d U P D 0.51(3) A 2
H H4B 0.443087 0.650925 0.662573 0.059000 Uiso calc U P R 0.51(3) A 2
C C3B 0.451(4) 0.5617(6) 0.7677(15) 0.049(4) Uani d U P D 0.51(3) A 2
H H3B 0.437269 0.575295 0.879656 0.059000 Uiso calc U P R 0.51(3) A 2
C C2B 0.461(3) 0.4983(7) 0.7318(15) 0.043(4) Uani d U P D 0.51(3) A 2
H H2B 0.442398 0.467839 0.817292 0.052000 Uiso calc U P R 0.51(3) A 2
N N1 0.6503(8) 0.7339(2) 0.9499(7) 0.0444(13) Uani d . . . 1.000000 . .
H H1AN 0.651956 0.698955 1.010287 0.053000 Uiso calc U . R 1.000000 . .
H H1BN 0.749002 0.751921 0.919446 0.053000 Uiso calc U . R 1.000000 . .
N N2 0.3515(8) 0.7334(2) 0.9488(7) 0.0432(13) Uani d . . . 1.000000 . .
H H2AN 0.351631 0.698380 1.009258 0.052000 Uiso calc U . R 1.000000 . .
H H2BN 0.251997 0.750733 0.918153 0.052000 Uiso calc U . R 1.000000 . .
N N3 0.4994(9) 0.8121(3) 0.8110(7) 0.0500(14) Uani d . . . 1.000000 . .
H H3AN 0.399966 0.829194 0.778971 0.060000 Uiso calc U . R 1.000000 . .
H H3BN 0.598965 0.829641 0.781386 0.060000 Uiso calc U . R 1.000000 . .
C C6 0.4993(9) 0.7595(3) 0.9047(7) 0.0397(14) Uani d . . . 1.000000 . .
C C4G 0.987(4) 0.5586(7) 0.0119(12) 0.126(8) Uani d U P DG 0.500000 B -1
H H4G 0.979721 0.559943 0.129929 0.152000 Uiso calc U P R 0.500000 B -1
C C1G 0.987(3) 0.6149(5) -0.0791(14) 0.105(8) Uani d U P G 0.500000 B -1
H H1G 0.979712 0.654734 -0.023370 0.126000 Uiso calc U P R 0.500000 B -1
C C6G 0.999(4) 0.6130(5) -0.2518(14) 0.125(9) Uani d U P G 0.500000 B -1
H H6G 0.998621 0.651471 -0.314020 0.150000 Uiso calc U P R 0.500000 B -1
C C2G 1.010(5) 0.5547(7) -0.3334(13) 0.162(10) Uani d U P G 0.500000 B -1
H H2G 1.017539 0.553417 -0.451372 0.194000 Uiso calc U P R 0.500000 B -1
C C3G 1.010(4) 0.4984(5) -0.242(2) 0.171(10) Uani d U P DG 0.500000 B -1
H H3G 1.017548 0.458625 -0.298076 0.206000 Uiso calc U P R 0.500000 B -1
C C5G 0.999(4) 0.5004(5) -0.070(2) 0.136(8) Uani d U P DG 0.500000 B -1
C C7G 0.991(4) 0.4434(7) 0.042(2) 0.181(7) Uani d U P D 0.500000 B -1
C C8G 1.044(4) 0.4482(9) 0.222(2) 0.181(7) Uani d U P D 0.500000 B -1
H H8G 1.167641 0.463118 0.226349 0.218000 Uiso calc U P R 0.500000 B -1
Cl Cl1 1.038(4) 0.3687(7) 0.287(3) 0.370(16) Uani d U P D 0.500000 B -1
C C9G 0.940(6) 0.4852(12) 0.351(4) 0.181(7) Uani d U P D 0.500000 B -1
H H9GA 0.815316 0.475747 0.337965 0.272000 Uiso calc U P R 0.500000 B -1
H H9GB 0.959486 0.530920 0.335869 0.272000 Uiso calc U P R 0.500000 B -1
H H9GC 0.978151 0.472564 0.462881 0.272000 Uiso calc U P R 0.500000 B -1
O O1G 0.954(5) 0.3918(7) -0.008(3) 0.252(16) Uani d U P D 0.500000 B -1
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 112.7(3) ?
O2 S1 O3 . . 111.0(3) ?
O1 S1 O3 . . 112.5(3) ?
O2 S1 C5 . . 107.2(3) ?
O1 S1 C5 . . 106.0(3) ?
O3 S1 C5 . . 107.0(3) ?
C4A C5 C1 . 3_666 121.0(8) ?
C4B C5 C1 . 3_666 121.1(8) ?
C4A C5 S1 . . 117.2(8) ?
C4B C5 S1 . . 117.2(7) ?
C1 C5 S1 3_666 . 120.1(5) ?
C1 C1 C2A 3_666 . 119.1(9) ?
C1 C1 C5 3_666 3_666 116.9(7) ?
C2A C1 C5 . 3_666 122.4(8) ?
C1 C1 C2B 3_666 . 119.2(9) ?
C5 C1 C2B 3_666 . 122.4(8) ?
C5 C4A C3A . . 119.9(12) ?
C5 C4A H4A . . 120.000000 ?
C3A C4A H4A . . 120.000000 ?
C2A C3A C4A . . 120.4(12) ?
C2A C3A H3A . . 119.800000 ?
C4A C3A H3A . . 119.800000 ?
C3A C2A C1 . . 120.5(12) ?
C3A C2A H2A . . 119.700000 ?
C1 C2A H2A . . 119.800000 ?
C5 C4B C3B . . 120.4(12) ?
C5 C4B H4B . . 119.800000 ?
C3B C4B H4B . . 119.800000 ?
C2B C3B C4B . . 120.1(11) ?
C2B C3B H3B . . 119.900000 ?
C4B C3B H3B . . 119.900000 ?
C3B C2B C1 . . 120.5(11) ?
C3B C2B H2B . . 119.700000 ?
C1 C2B H2B . . 119.700000 ?
C6 N1 H1AN . . 120.000000 ?
C6 N1 H1BN . . 120.000000 ?
H1AN N1 H1BN . . 120.000000 ?
C6 N2 H2AN . . 120.000000 ?
C6 N2 H2BN . . 120.000000 ?
H2AN N2 H2BN . . 120.000000 ?
C6 N3 H3AN . . 120.000000 ?
C6 N3 H3BN . . 120.000000 ?
H3AN N3 H3BN . . 120.000000 ?
N2 C6 N1 . . 120.8(5) ?
N2 C6 N3 . . 120.1(6) ?
N1 C6 N3 . . 119.1(6) ?
C1G C4G C5G . . 120.000000 ?
C1G C4G H4G . . 120.000000 ?
C5G C4G H4G . . 120.000000 ?
C4G C1G C6G . . 120.000000 ?
C4G C1G H1G . . 120.000000 ?
C6G C1G H1G . . 120.000000 ?
C1G C6G C2G . . 120.000000 ?
C1G C6G H6G . . 120.000000 ?
C2G C6G H6G . . 120.000000 ?
C3G C2G C6G . . 120.000000 ?
C3G C2G H2G . . 120.000000 ?
C6G C2G H2G . . 120.000000 ?
C5G C3G C2G . . 120.000000 ?
C5G C3G H3G . . 120.000000 ?
C2G C3G H3G . . 120.000000 ?
C3G C5G C4G . . 120.000000 ?
C3G C5G C7G . . 125.2(10) ?
C4G C5G C7G . . 114.8(10) ?
O1G C7G C5G . . 122.6(11) ?
O1G C7G C8G . . 116.6(11) ?
C5G C7G C8G . . 120.6(12) ?
C7G C8G C9G . . 124.(2) ?
C7G C8G Cl1 . . 102.5(14) ?
C9G C8G Cl1 . . 105.4(16) ?
C7G C8G H8G . . 108.200000 ?
C9G C8G H8G . . 108.000000 ?
Cl1 C8G H8G . . 108.200000 ?
C8G C9G H9GA . . 109.400000 ?
C8G C9G H9GB . . 109.500000 ?
H9GA C9G H9GB . . 109.500000 ?
C8G C9G H9GC . . 109.600000 ?
H9GA C9G H9GC . . 109.500000 ?
H9GB C9G H9GC . . 109.500000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 S1 . 1.455(5) ?
O2 S1 . 1.447(5) ?
O3 S1 . 1.467(5) ?
S1 C5 . 1.777(6) ?
C5 C4A . 1.368(14) ?
C5 C4B . 1.368(14) ?
C5 C1 3_666 1.432(8) ?
C1 C1 3_666 1.427(10) ?
C1 C2A . 1.427(14) ?
C1 C2B . 1.432(13) ?
C4A C3A . 1.409(15) ?
C4A H4A . 0.950000 ?
C3A C2A . 1.362(15) ?
C3A H3A . 0.950000 ?
C2A H2A . 0.950000 ?
C4B C3B . 1.410(14) ?
C4B H4B . 0.950000 ?
C3B C2B . 1.364(14) ?
C3B H3B . 0.950000 ?
C2B H2B . 0.950000 ?
N1 C6 . 1.325(9) ?
N1 H1AN . 0.880000 ?
N1 H1BN . 0.880000 ?
N2 C6 . 1.307(8) ?
N2 H2AN . 0.880000 ?
N2 H2BN . 0.880000 ?
N3 C6 . 1.336(7) ?
N3 H3AN . 0.880000 ?
N3 H3BN . 0.880000 ?
C4G C1G . 1.390000 ?
C4G C5G . 1.390000 ?
C4G H4G . 0.950000 ?
C1G C6G . 1.390000 ?
C1G H1G . 0.950000 ?
C6G C2G . 1.390000 ?
C6G H6G . 0.950000 ?
C2G C3G . 1.390000 ?
C2G H2G . 0.950000 ?
C3G C5G . 1.390000 ?
C3G H3G . 0.950000 ?
C5G C7G . 1.495(9) ?
C7G O1G . 1.188(16) ?
C7G C8G . 1.502(10) ?
C8G C9G . 1.523(10) ?
C8G Cl1 . 1.752(17) ?
C8G H8G . 1.000000 ?
C9G H9GA . 0.980000 ?
C9G H9GB . 0.980000 ?
C9G H9GC . 0.980000 ?
