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_4123062
_publ_section_title
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 Lock-Arm Supramolecular Ordering: A Molecular Construction Set for
 Cocrystallizing Organic Charge Transfer Complexes.
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_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         'C10 H10 N2, C22 H22 N2 O8'
_chemical_formula_sum            'C32 H32 N4 O8'
_chemical_formula_weight         600.61
_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
_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                72.093(2)
_cell_angle_beta                 76.054(2)
_cell_angle_gamma                80.941(2)
_cell_formula_units_Z            1
_cell_length_a                   6.9510(2)
_cell_length_b                   8.6966(2)
_cell_length_c                   12.1281(3)
_cell_measurement_reflns_used    3049
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.47
_cell_volume                     674.30(3)
_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)'
_diffrn_ambient_temperature      100.02
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.982
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12520
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.062
_diffrn_reflns_theta_min         1.803
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0769 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8288.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3880
_refine_ls_number_restraints     153
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1357
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.093
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1250P)^2^+0.1323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2129
_refine_ls_wR_factor_ref         0.2540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2073
_reflns_number_total             3880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509442t_si_008.cif
_cod_data_source_block           n0442_cs
_cod_database_code               4123062
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.952
_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. Restrained distances
 C21-C17 \\sim C17-C24 \\sim C22-C23
 with sigma of 0.02
 C21-C22 \\sim C22-C17 \\sim C17-C23 \\sim C23-C24
 with sigma of 0.02
 N3-C17 \\sim N3-C24
 with sigma of 0.02
3. Rigid bond restraints
 C20, C19, C18, C17, C16, C24, C22, C23, C21, C17A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C20 \\sim C19 \\sim C18 \\sim C17 \\sim C16 \\sim C24 \\sim C22 \\sim C23 \\sim
C21 \\sim C17A: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
5. Same fragment restrains
{C11, C13, O4}
as
{C12, C15, O5}
6. Others
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(O5)=Sof(H5A)=1-
 FVAR(1)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(O4)=Sof(H4)=
 FVAR(1)
 Sof(N3)=Sof(H3A)=Sof(H3B)=Sof(C23)=Sof(C17)=Sof(C22)=Sof(H22)=Sof(C21)=
 Sof(H21)=Sof(C24)=Sof(H24)=1-FVAR(2)
 Sof(C20)=Sof(H20)=Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(C16)=Sof(C17A)=Sof(C18)=
 Sof(H18)=Sof(C19)=Sof(H19)=FVAR(2)
7.a Rotating group:
 N2(H2A,H2B), N3(H3A,H3B)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C12(H12A,H12B),
 C15(H15A,H15B)
7.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C19(H19), C22(H22), C21(H21), C24(H24), C1(H1), C5(H5)
7.d Tetrahedral OH refined with riding coordinates:
 O5(H5A)
7.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'