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_7154790
_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_formula_sum            'C15 H25 N O3'
_chemical_formula_weight         267.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-09-28 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.033(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7556(12)
_cell_length_b                   10.6790(15)
_cell_length_c                   9.8996(16)
_cell_measurement_temperature    173(2)
_cell_volume                     783.9(2)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8393
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.041
_diffrn_reflns_theta_min         4.672
_exptl_absorpt_coefficient_mu    0.625
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.160
_refine_ls_abs_structure_details
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.890
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                2625
_reflns_number_total             2736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02023a3.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 7154788--7154790.cif.'
_cod_database_code               7154790
_shelx_estimated_absorpt_t_min   0.849
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2014-3
_shelx_res_checksum              37320