Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.
Yin, Zhiwei; Zhang, Jinzhu; Wu, Jing; Green, Riana; Li, Sihan; Zheng, Shengping; Organic & biomolecular chemistry 12 (2014) 2854–2858; doi:10.1039/c4ob00391h

data_7153702
_publ_section_title
;
 Synthesis of o-chlorophenols via an unexpected nucleophilic chlorination
 of quinone monoketals mediated by N,N'-dimethylhydrazine dihydrochloride.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2854
_journal_page_last               2858
_journal_paper_doi               10.1039/c4ob00391h
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C9 H11 Cl O3'
_chemical_formula_weight         202.63
_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                 92.227(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2268(5)
_cell_length_b                   8.9268(9)
_cell_length_c                   19.809(2)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.49
_cell_measurement_theta_min      2.50
_cell_volume                     923.56(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19279
_diffrn_reflns_theta_full        28.49
_diffrn_reflns_theta_max         28.49
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.9238
_exptl_absorpt_correction_T_min  0.8196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0342P)^2^+0.4173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                2246
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00391h2.cif
_cod_data_source_block           13spz2h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        923.59(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7153702