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_1555564
_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_absolute_configuration ad
_chemical_formula_moiety         'C16 H24 N2 O3 S'
_chemical_formula_sum            'C16 H24 N2 O3 S'
_chemical_formula_weight         324.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-07-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6938(12)
_cell_length_b                   9.8115(11)
_cell_length_c                   18.943(2)
_cell_measurement_reflns_used    2175
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      23.436
_cell_measurement_theta_min      2.578
_cell_volume                     1615.8(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7816
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_min         2.338
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.0874
_exptl_absorpt_correction_T_min  0.0655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.7494.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       Block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.185
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2923
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0436P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2464
_reflns_number_total             2923
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01047_si_001.cif
_cod_data_source_block           Shenvi47
_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               1555564
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. 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
2. Restrained distances
 N2-H2B = N2-H2A = N1-H1B = N1-H1A
 0.95 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
3.d X=CH2 refined with riding coordinates:
 C1(H1C,H1D)
3.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_shelx_res_checksum              11610
_shelx_hkl_checksum              90196
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'