Fluorine in fragrances: exploring the difluoromethylene (CF2) group as a conformational constraint in macrocyclic musk lactones.
Corr, Michael J.; Cormanich, Rodrigo A.; von Hahmann, Cortney N.; Bühl, Michael; Cordes, David B.; Slawin, Alexandra M. Z.; O'Hagan, David; Organic & biomolecular chemistry 14 (2016) 211–219; doi:10.1039/c5ob02023a

data_7154788
_publ_section_title
;
 Fluorine in fragrances: exploring the difluoromethylene (CF2) group as a
 conformational constraint in macrocyclic musk lactones.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              211
_journal_page_last               219
_journal_paper_doi               10.1039/c5ob02023a
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H22 F4 O2'
_chemical_formula_sum            'C14 H22 F4 O2'
_chemical_formula_weight         298.32
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.135(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.1961(6)
_cell_length_b                   9.1334(6)
_cell_length_c                   17.5805(11)
_cell_measurement_reflns_used    9089
_cell_measurement_temperature    125
_cell_measurement_theta_max      67.88
_cell_measurement_theta_min      4.84
_cell_volume                     1465.18(16)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      125
_diffrn_detector_area_resol_mean 29.257
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18512
_diffrn_reflns_theta_full        68.14
_diffrn_reflns_theta_max         68.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.290
_refine_ls_abs_structure_details
;   
 Flack x determined using 1656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.18(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4925
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0610P)^2^+1.5896P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1415
_reflns_number_gt                4311
_reflns_number_total             4925
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c5ob02023a3.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7154788--7154790.cif.'
_cod_original_cell_volume        1465.18(17)
_cod_database_code               7154788