Direct halogenative dearomatization of 2-naphthols by NXS (X = Cl, Br) in water
Zhang, Zhenbei; Sun, Qiangsheng; Xu, Daqian; Xia, Chungu; Sun, Wei; Green Chem. 18 (2016) 5485–; doi:10.1039/C6GC01673A

data_7225884
_publ_section_title
;
 Direct halogenative dearomatization of 2-naphthols by NXS (X = Cl, Br) in
 water
;
_journal_issue                   20
_journal_name_full               'Green Chem.'
_journal_page_first              5485
_journal_paper_doi               10.1039/C6GC01673A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-01
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-03 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.690(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8686(3)
_cell_length_b                   6.9699(3)
_cell_length_c                   27.0903(10)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    294.9(3)
_cell_measurement_theta_max      25.7430
_cell_measurement_theta_min      3.8710
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -14.00   11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  -39.0000  -73.0000 25

  2 omega  -19.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858  -99.0000  -60.0000 46

  3 omega  -20.00   22.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858  -99.0000 -150.0000 42

  4 omega  -32.00   -7.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858   39.0000   81.0000 25

  5 omega   38.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108   39.0000   81.0000 26

  6 omega   35.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0108  178.0000 -180.0000 80

  7 omega  -98.00  -47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.8858  -39.0000  -73.0000 51

  8 omega  -52.00  -25.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.0420   38.0000    0.0000 27

  9 omega   18.00   89.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       27.1670   57.0000 -120.0000 71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0353180000
_diffrn_orient_matrix_UB_12      0.0809439000
_diffrn_orient_matrix_UB_13      -0.0127651000
_diffrn_orient_matrix_UB_21      -0.0724740000
_diffrn_orient_matrix_UB_22      -0.0436036000
_diffrn_orient_matrix_UB_23      -0.0004768000
_diffrn_orient_matrix_UB_31      -0.0069452000
_diffrn_orient_matrix_UB_32      0.0435957000
_diffrn_orient_matrix_UB_33      0.0232030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            8721
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.295
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0462P)^2^+0.7599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1434
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2148
_reflns_number_total             3249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6gc01673a2.cif
_cod_data_source_block           zhangzhb_0531
_cod_depositor_comments          'Adding full bibliography for 7225884.cif.'
_cod_original_cell_volume        1655.31(11)
_cod_database_code               7225884
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C20(H20), C15(H15), C19(H19), C14(H14), C17(H17), C18(H18),
 C7(H7), C6(H6), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C11(H11A,H11B,H11C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-31
_olex2_submission_special_instructions 'No special instructions were received'