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_4123058
_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         '2(C18 H20 N2 O8), C10 H9 N O'
_chemical_formula_sum            'C46 H49 N5 O17'
_chemical_formula_weight         943.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                71.882(9)
_cell_angle_beta                 81.810(9)
_cell_angle_gamma                84.105(8)
_cell_formula_units_Z            1
_cell_length_a                   6.7603(7)
_cell_length_b                   10.8522(11)
_cell_length_c                   15.785(2)
_cell_measurement_reflns_used    3143
_cell_measurement_temperature    84(2)
_cell_measurement_theta_max      63.98
_cell_measurement_theta_min      2.97
_cell_volume                     1087.3(2)
_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      84.64
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.779
_diffrn_measured_fraction_theta_max 0.971
_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  0.0497
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.779
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8112
_diffrn_reflns_point_group_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         59.131
_diffrn_reflns_theta_min         5.939
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.4791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1046 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.6366. The \l/2 correction factor is 0.0000.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.722
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1060P)^2^+0.2340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2259
_reflns_number_total             3058
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509442t_si_002.cif
_cod_data_source_block           n0571_ncs
_cod_database_code               4123058
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.551
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Shared sites
{O14, N14A}
3. Uiso/Uaniso restraints and constraints
Uiso(O14) = Uiso(N14A)
4. Others
 Fixed Sof: O14(0.5) H14(0.5) N14A(0.5) H14A(0.5) H14B(0.5)
5.a Rotating group:
 N14A(H14A,H14B)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,
 H29B), C31(H31A,H31B), C32(H32A,H32B), C34(H34A,H34B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C25(H25), C30(H30), C33(H33)
5.d Tetrahedral OH refined with riding coordinates:
 O14(H14)
5.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O13(H13)
;
_olex2_submission_special_instructions 'No special instructions were received'