Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of Isopulegol.
Crossley, Steven W. M.; Martinez, Ruben M.; Guevara-Zuluaga, Sebastián; Shenvi, Ryan A.; Organic letters 18 (2016) 2620–2623; doi:10.1021/acs.orglett.6b01047

data_1555565
_publ_section_title
;
 Synthesis of the Privileged 8-Arylmenthol Class by Radical Arylation of
 Isopulegol.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2620
_journal_page_last               2623
_journal_paper_doi               10.1021/acs.orglett.6b01047
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C21 H22 N2 O6'
_chemical_formula_sum            'C21 H22 N2 O6'
_chemical_formula_weight         398.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                91.394(4)
_cell_angle_beta                 99.881(4)
_cell_angle_gamma                90.214(4)
_cell_formula_units_Z            4
_cell_length_a                   7.7666(5)
_cell_length_b                   15.5767(6)
_cell_length_c                   16.2634(6)
_cell_measurement_reflns_used    1480
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.52
_cell_measurement_theta_min      5.68
_cell_volume                     1937.69(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.10-0 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18445
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         68.484
_diffrn_reflns_theta_min         2.759
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0870 before and 0.0326 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1120 before and 0.0347 after correction.
 The Ratio of minimum to maximum transmission is 0.92.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 49200 reflections, Rint = 0.0352
 (28809 with I > 3sig(I), Rint = 0.0300)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     527
_refine_ls_number_reflns         18445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+0.6726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16099
_reflns_number_total             18445
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01047_si_002.cif
_cod_data_source_block           twin4_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1555565
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5869(8) 0.4131(8)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C14(H14), C7'(H7'), C9'(H9'), C14'(H14')
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C10'(H10C,
 H10D), C11'(H11C,H11D), C12'(H12C,H12D), C13'(H13C,H13D)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C19(H19), C21(H21),
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C17'(H17'), C19'(H19'),
 C21'(H21')
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8'(H8'A,H8'B,H8'C)
;
_shelx_res_checksum              10963
_shelx_hkl_checksum              1117
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'