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_4123064
_publ_section_title
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 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         'C16 H11 N, 2(C11 H11 N O4)'
_chemical_formula_sum            'C38 H33 N3 O8'
_chemical_formula_weight         659.67
_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                94.620(5)
_cell_angle_beta                 112.518(5)
_cell_angle_gamma                109.840(5)
_cell_formula_units_Z            2
_cell_length_a                   10.9811(8)
_cell_length_b                   12.4287(8)
_cell_length_c                   12.9441(9)
_cell_measurement_reflns_used    1870
_cell_measurement_temperature    85(2)
_cell_measurement_theta_max      63.86
_cell_measurement_theta_min      3.90
_cell_volume                     1489.3(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)'
_diffrn_ambient_temperature      85.28
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.906
_diffrn_measured_fraction_theta_max 0.964
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.906
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13584
_diffrn_reflns_point_group_measured_fraction_full 0.906
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.856
_diffrn_reflns_theta_min         3.810
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8714.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       plate
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1061P)^2^+0.1028P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1798
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3438
_reflns_number_total             4883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja509442t_si_007.cif
_cod_data_source_block           n0575_cs
_cod_original_cell_volume        1489.33(19)
_cod_database_code               4123064
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H1BA,H1BB} of N1B, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H1AA,H1AB} of N1A
2. Shared sites
{C2A, C2B}
{C14A, C14B}
3. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(C2B)
Uanis(C14A) = Uanis(C14B)
4. Others
 Sof(C2B)=Sof(H2B)=Sof(C14A)=Sof(N1B)=Sof(H1BA)=Sof(H1BB)=1-FVAR(1)
 Sof(C2A)=Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(C14B)=Sof(H14B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C28(H28A,
 H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3(H3), C6(H6), C8(H8), C9(H9), C11(H11), C14B(H14B), C15(H15),
 C23(H23), C27(H27), C36(H36), C38(H38)
5.c Tetrahedral OH refined with riding coordinates:
 O1(H1A), O5(H5)
5.d X=CH2 refined with riding coordinates:
 N1B(H1BA,H1BB)
;
_olex2_submission_special_instructions 'No special instructions were received'