The 2,6-dimercaptoazulene motif: efficient synthesis and completely regioselective metallation of its 6-mercapto terminus
Scheetz, Kolbe J.; Spaeth, Andrew D.; Vorushilov, Alexander S.; Powell, Douglas R.; Day, Victor W.; Barybin, Mikhail V.; Chemical Science 4 (2013) 4267–; doi:10.1039/c3sc51773j

data_1514728
_publ_section_title
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 The 2,6-dimercaptoazulene motif: efficient synthesis and completely
 regioselective metallation of its 6-mercapto terminus
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_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              4267
_journal_paper_doi               10.1039/c3sc51773j
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C34 H30 Au O4 P S2'
_chemical_formula_sum            'C34 H30 Au O4 P S2'
_chemical_formula_weight         794.64
_chemical_melting_point          180.0(10)
_chemical_name_common
'[PPh3Au](1,3-diethoxycarbonyl-2-mercapto-6-azulenethiolate)'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                   23.574(2)
_cell_length_b                   11.1504(10)
_cell_length_c                   23.342(2)
_cell_measurement_reflns_used    7184
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.20
_cell_volume                     6135.7(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            37712
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    5.022
_exptl_absorpt_correction_T_max  0.5840
_exptl_absorpt_correction_T_min  0.2964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.203
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.240(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         10050
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0294
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+11.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0698
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                9157
_reflns_number_total             10050
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3sc51773j.txt
_cod_data_source_block           12027
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '179 - 181' was changed to
'180.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

data name '_iucr_refine_instruction_details' was replaced with
'_iucr_refine_instructions_details' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
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_cod_database_code               1514728