Additivity of Substituent Effects in Aromatic Stacking Interactions.
Hwang, Jungwun; Li, Ping; Carroll, William R.; Smith, Mark D.; Pellechia, Perry J.; Shimizu, Ken D.; Journal of the American Chemical Society 136 (2014) 14060–; doi:10.1021/ja504378p

data_4122722
_publ_section_title
;
 Additivity of Substituent Effects in Aromatic Stacking Interactions.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14060
_journal_paper_doi               10.1021/ja504378p
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C46 H30 Cl N O4'
_chemical_formula_sum            'C46 H30 Cl N O4'
_chemical_formula_weight         696.16
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                80.080(2)
_cell_angle_beta                 80.090(2)
_cell_angle_gamma                80.508(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6849(9)
_cell_length_b                   11.8004(11)
_cell_length_c                   16.0900(15)
_cell_measurement_reflns_used    3780
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.687
_cell_measurement_theta_min      2.346
_cell_volume                     1766.9(3)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.631 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20337
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.061
_diffrn_reflns_theta_min         1.769
_diffrn_source_current           37.0
_diffrn_source_power             1.739
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       plate
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6254
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0609P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4505
_reflns_number_total             6254
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja504378p_si_003.cif
_cod_data_source_block           hjb67csq_sq
_cod_depositor_comments
'Adding full bibliography for 4122721--4122722.cif.'
_cod_database_code               4122722
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O4-C40A \\sim O4-C40B
 with sigma of 0.0025
 C44A-C46A \\sim C44B-C46B
 with sigma of 0.02
 C43A-Cl1A \\sim C43B-Cl1B
 with sigma of 0.0033
3. Uiso/Uaniso restraints and constraints
Uanis(C40A) = Uanis(C40B)
4. Others
 Fixed Sof: Cl1A(0.5) C40A(0.5) C41A(0.5) H41A(0.5) C42A(0.5) H42A(0.5)
 C43A(0.5) C44A(0.5) C45A(0.5) H45A(0.5) C46A(0.5) H46A(0.5) H46B(0.5)
 H46C(0.5) Cl1B(0.5) C40B(0.5) C41B(0.5) H41B(0.5) C42B(0.5) H42B(0.5)
 C43B(0.5) C44B(0.5) C45B(0.5) H45B(0.5) C46B(0.5) H46D(0.5) H46E(0.5) H46F(0.5)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18), C19(H19),
 C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C36(H36), C37(H37), C38(H38), C39(H39),
 C41A(H41A), C42A(H42A), C45A(H45A), C41B(H41B), C42B(H42B), C45B(H45B)
5.c Fitted hexagon refined as free rotating group:
 C40A(C41A,C42A,C43A,C44A,C45A), C40B(C41B,C42B,C43B,C44B,C45B)
5.d Idealised Me refined as rotating group:
 C46A(H46A,H46B,H46C), C46B(H46D,H46E,H46F)
;
_shelx_res_checksum              38
_shelx_hkl_checksum              30424
_shelx_fab_checksum              73739
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'