Synthesis and solid state structure of a hydrazone-disulfide macrocycle and its dynamic covalent ring-opening under acidic and basic conditions.
von Delius, Max; Geertsema, Edzard M.; Leigh, David A.; Slawin, Alexandra M. Z.; Organic & biomolecular chemistry 8 (2010) 4617–4624; doi:10.1039/c0ob00214c

data_7153457
_publ_section_title
;
 Synthesis and solid state structure of a hydrazone-disulfide macrocycle
 and its dynamic covalent ring-opening under acidic and basic conditions.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4617
_journal_page_last               4624
_journal_paper_doi               10.1039/c0ob00214c
_journal_volume                  8
_journal_year                    2010
_chemical_formula_moiety         'C18 H18 N2 O2 S2'
_chemical_formula_sum            'C18 H18 N2 O2 S2'
_chemical_formula_weight         358.46
_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                 96.481(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.886(2)
_cell_length_b                   9.252(3)
_cell_length_c                   26.755(8)
_cell_measurement_reflns_used    4729
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.0248
_cell_measurement_theta_min      2.3308
_cell_volume                     1693.6(9)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14385
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9163
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.0800
_exptl_crystal_size_mid          0.0800
_exptl_crystal_size_min          0.0800
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.050(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.949
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+4.5674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2864
_reflns_number_total             2984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00214c.txt
_cod_data_source_block           dled165
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1693.5(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153457