Internal and External Stereoisomers of Squaraine Rotaxane Endoperoxide: Synthesis, Chemical Differences, and Structural Revision.
Collins, Carleton G.; Lee, Joshua M.; Oliver, Allen G.; Wiest, Olaf; Smith, Bradley D.; The Journal of organic chemistry 79 (2014) 1120–; doi:10.1021/jo402564k

data_4029034
_publ_section_title
;
 Internal and External Stereoisomers of Squaraine Rotaxane Endoperoxide:
 Synthesis, Chemical Differences, and Structural Revision.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1120
_journal_paper_doi               10.1021/jo402564k
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C28 H28 N2 O4, C H2 Cl2'
_chemical_formula_sum            'C14.5 H15 Cl N O2'
_chemical_formula_weight         270.72
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 102.553(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5010(9)
_cell_length_b                   6.6118(3)
_cell_length_c                   28.1947(13)
_cell_measurement_reflns_used    2438
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.10
_cell_measurement_theta_min      6.25
_cell_volume                     2638.6(2)
_computing_cell_refinement       'Bruker SAINT v8.18C'
_computing_data_collection       'Bruker APEX-II v2012-10.0'
_computing_data_reduction        'Bruker SAINT v8.18C'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT-2012/2 (Sheldrick, 2012)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            9543
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.163
_diffrn_reflns_theta_min         6.253
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    2.527
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.7557
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       blade
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0574P)^2^+3.0499P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1966
_reflns_number_total             2488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402564k_si_003.cif
_cod_data_source_block           nd1305
_cod_original_formula_sum        'C14.50 H15 Cl N O2'
_cod_database_code               4029034
_shelx_estimated_absorpt_t_min   0.474
_shelx_estimated_absorpt_t_max   0.919
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelxl_version_number           2012-9