Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
Rutledge, Kelli M.; Griesbach, Caleb; Mercado, Brandon Q.; Peczuh, Mark W.; Acta Crystallographica Section E 76 (2020) 1617–1623; doi:10.1107/S2056989020012037

data_2243668
_publ_section_title
;
 Structures of three disubstituted [13]-macrodilactones reveal effects of
 substitution on macrocycle conformation
;
_journal_coeditor_code           MW2168
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1617
_journal_page_last               1623
_journal_paper_doi               10.1107/S2056989020012037
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C18 H22 O4'
_chemical_formula_moiety         'C18 H22 O4'
_chemical_formula_sum            'C18 H22 O4'
_chemical_formula_weight         302.35
_chemical_name_common            III
_chemical_name_systematic
;
<i>trans</i>-11-Methyl-4-phenyl-1,10-dioxacyclotridec-5-ene-2,9-dione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2952(8)
_cell_length_b                   20.9595(15)
_cell_length_c                   6.6840(5)
_cell_measurement_reflns_used    576
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1582.4(2)
_computing_cell_refinement
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2011)
;
_computing_data_collection
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2011)
;
_computing_data_reduction
;
<i>CrystalClear-SM Expert</i> (Rigaku, 2011)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>CIFTAB2014/2</i> (Sheldrick, 2014)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 6.8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            26669
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.671
_diffrn_reflns_theta_min         2.651
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>REQAB</i>; Jacobson, 1998)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       Prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details
;
Flack x determined using 1473 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014/7 (Sheldrick 2015b)
;
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3664
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0578P)^2^+0.8966P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                3410
_reflns_number_total             3664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            mw2168sup1.cif
_cod_data_source_block           III
_cod_database_code               2243668
_cod_database_fobs_code          2243668
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.982
_shelx_hkl_checksum              21160
_shelx_res_checksum              78709