Lock-Arm Supramolecular Ordering: A Molecular Construction Set for Cocrystallizing Organic Charge Transfer Complexes.
Blackburn, Anthea K.; Sue, Andrew C.-H.; Shveyd, Alexander K.; Cao, Dennis; Tayi, Alok; Narayanan, Ashwin; Rolczynski, Brian S.; Szarko, Jodi M.; Bozdemir, Ozgur A.; Wakabayashi, Rie; Lehrman, Jessica A.; Kahr, Bart; Chen, Lin X.; Nassar, Majed S.; Stupp, Samuel I.; Stoddart, J. Fraser; Journal of the American Chemical Society  (2014) 141124065827003–; doi:10.1021/ja509442t

data_4123063
_publ_section_title
;
 Lock-Arm Supramolecular Ordering: A Molecular Construction Set for
 Cocrystallizing Organic Charge Transfer Complexes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141124065827003
_journal_paper_doi               10.1021/ja509442t
_journal_year                    2014
_chemical_formula_moiety         'C18 H20 N2 O8, C8 H8 O2 S4'
_chemical_formula_sum            'C26 H28 N2 O10 S4'
_chemical_formula_weight         656.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.157(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9236(4)
_cell_length_b                   6.9553(3)
_cell_length_c                   16.7123(5)
_cell_measurement_reflns_used    3711
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      64.54
_cell_measurement_theta_min      4.12
_cell_volume                     1343.89(8)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      84.91
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.890
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7784
_diffrn_reflns_point_group_measured_fraction_full 0.890
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.686
_diffrn_reflns_theta_min         4.118
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    3.813
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.5385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1125 before and 0.0527 after correction.
The Ratio of minimum to maximum transmission is 0.7156.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_description       tablet
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.666
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.815
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+1.3700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1939
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509442t_si_005.cif
_cod_data_source_block           p21-n
_cod_database_code               4123063
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.748
_shelx_estimated_absorpt_t_min   0.186
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1-H1
 1.12 with sigma of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'