Organocatalytic asymmetric chlorinative dearomatization of naphthols
Yin, Qin; Wang, Shou-Guo; Liang, Xiao-Wei; Gao, De-Wei; Zheng, Jun; You, Shu-Li; Chem. Sci. 6 (2015) 4179–; doi:10.1039/C5SC00494B

data_1519413
_publ_section_title
;
 Organocatalytic asymmetric chlorinative dearomatization of naphthols
;
_journal_issue                   7
_journal_name_full               'Chem. Sci.'
_journal_page_first              4179
_journal_paper_doi               10.1039/C5SC00494B
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H9 Cl O3'
_chemical_formula_weight         236.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-02-07 deposited with the CCDC.
2015-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.632(2)
_cell_length_b                   9.726(2)
_cell_length_c                   11.729(3)
_cell_measurement_reflns_used    4191
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      55.190
_cell_measurement_theta_min      5.438
_cell_volume                     1098.8(4)
_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'
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_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
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_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7270
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
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_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         2.721
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
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_exptl_crystal_description       prismatic
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_exptl_crystal_size_max          0.211
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_refine_diff_density_max         0.432
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 751 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(5)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2040
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.8707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1182
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1898
_reflns_number_total             2040
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00494b2.cif
_cod_data_source_block           dm14320
_cod_depositor_comments
'Adding full bibliography for 1519413--1519414.cif.'
_cod_original_cell_volume        1098.7(4)
_cod_database_code               1519413
_shelxl_version_number           2014-3
_shelx_res_checksum              61905
_shelx_hkl_checksum              36849