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_4122721
_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         'C47 H33 N O4, 1.34(C D Cl3)'
_chemical_formula_sum            'C48.34 H33 Cl4.02 D1.34 N O4'
_chemical_formula_weight         836.90
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.762(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.158(3)
_cell_length_b                   15.794(3)
_cell_length_c                   16.302(3)
_cell_measurement_reflns_used    2827
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.727
_cell_measurement_theta_min      2.579
_cell_volume                     4040.8(13)
_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 0.923
_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  0.0941
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            41215
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.332
_diffrn_reflns_theta_min         1.821
_diffrn_source                   'sealed tube'
_diffrn_source_current           38.0
_diffrn_source_power             1.8
_diffrn_source_voltage           47.0
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       plate
_exptl_crystal_F_000             1727
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         6571
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0658
_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^)+(0.0862P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1795
_reflns_number_gt                3760
_reflns_number_total             6571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja504378p_si_002.cif
_cod_data_source_block           hjb55m
_cod_depositor_comments
'Adding full bibliography for 4122721--4122722.cif.'
_cod_original_cell_volume        4041.0(12)
_cod_database_code               4122721
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.923
_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. Same fragment restrains
{Cl1, Cl2, Cl3, C81}
as
{Cl4, Cl5, Cl6, C82}
{Cl1, Cl2, Cl3, C81}
as
{Cl10, Cl11, Cl12, C84}
{Cl1, Cl2, Cl3, C81}
as
{Cl7, Cl8, Cl9, C83}
{Cl1, Cl2, Cl3, C81}
as
{Cl13, Cl14, Cl15, C85}
3. Others
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C81)=Sof(D81)=FVAR(1)
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C82)=Sof(D82)=FVAR(2)
 Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(C83)=Sof(D83)=FVAR(3)
 Sof(Cl13)=Sof(Cl14)=Sof(Cl15)=Sof(C85)=Sof(D85)=FVAR(4)
 Sof(Cl10)=Sof(Cl11)=Sof(Cl12)=Sof(C84)=Sof(D84)=FVAR(5)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C81(D81), C82(D82), C84(D84), C83(D83), C85(D85)
4.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),
 C41(H41), C43(H43), C45(H45)
4.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C47(H47A,H47B,H47C)
;
_shelx_res_checksum              71624
_shelx_hkl_checksum              26422