Comparison crystal structure conformations of two structurally related biphenyl analogues: 4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and 4,4'-bis{3-[(<i>S</i>)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl
Wan, Anqi; Penthala, Narsimha Reddy; Fifer, E. Kim; Parkin, Sean; Crooks, Peter A.; Acta Crystallographica Section E 71 (2015) 1147–1150; doi:10.1107/S2056989015016163

data_2241139
_publ_section_title
;
 Comparison crystal structure conformations of two structurally related
 biphenyl analogues:
 4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and
 4,4'-bis{3-[(<i>S</i>)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl
;
_journal_coeditor_code           HG5457
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1147
_journal_page_last               1150
_journal_paper_doi               10.1107/S2056989015016163
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C28 H32 N2'
_chemical_formula_moiety         'C28 H32 N2'
_chemical_formula_sum            'C28 H32 N2'
_chemical_formula_weight         396.55
_chemical_name_systematic
;
4,4'-Bis{3-[(<i>S</i>)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 98.177(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1411(4)
_cell_length_b                   7.3080(4)
_cell_length_c                   18.9840(9)
_cell_measurement_reflns_used    2730
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1117.97(10)
_computing_cell_refinement
;
<i>SCALEPACK</i> (Otwinowski & Minor, 2006)
;
_computing_data_collection
;
<i>COLLECT</i> (Nonius, 1998)
;
_computing_data_reduction
;
<i>DENZO-SMN</i> (Otwinowski & Minor, 2006)
;
_computing_molecular_graphics
;
<i>XP in SHELXTL</i> (Sheldrick, 2008)
;
_computing_publication_material
;
<i>SHELX</i> (Sheldrick, 2008) and <i>CIFFIX</i> (Parkin, 2013)
;
_computing_structure_refinement
;
<i>SHELXL2014</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SHELXS97</i> (Sheldrick, 2008)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       '\f and \w scans at fixed \c = 55\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.168
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       'cut slab'
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.192
_refine_ls_abs_structure_details
;
Flack <i>x</i> parameter was determined using 1205 quotients of the form
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4705
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0742P)^2^+0.0409P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                3548
_reflns_number_total             4705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hg5457sup1.cif
_cod_data_source_block           II
_cod_database_code               2241139
_cod_database_fobs_code          2241139
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.995
_shelx_hkl_checksum              24615
_shelx_res_checksum              28138
_shelxl_version_number           2014/6