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_1514727
_publ_section_title
;
 The 2,6-dimercaptoazulene motif: efficient synthesis and completely
 regioselective metallation of its 6-mercapto terminus
;
_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         'C16 H14 Cl2 O4'
_chemical_formula_sum            'C16 H14 Cl2 O4'
_chemical_formula_weight         341.17
_chemical_melting_point          162
_chemical_name_common            2,6-dichloro-1,3-diethoxycarbonylazulene
_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                82.606(5)
_cell_angle_beta                 86.888(6)
_cell_angle_gamma                82.453(6)
_cell_formula_units_Z            2
_cell_length_a                   3.9099(11)
_cell_length_b                   13.413(4)
_cell_length_c                   14.207(4)
_cell_measurement_reflns_used    3427
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.24
_cell_volume                     731.9(4)
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7409
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.54
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  0.9686
_exptl_absorpt_correction_T_min  0.8167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.253
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0700
_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^)+(0.1200P)^2^+0.4400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.1876
_reflns_number_gt                1994
_reflns_number_total             2654
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3sc51773j.txt
_cod_data_source_block           11037
_cod_database_code               1514727