The CH-π Interactions of Methyl Ethers as a Model for Carbohydrate-N-Heteroarene Interactions.
Li, Ping; Parker, Trent M.; Hwang, Jungwun; Deng, Fengyuan; Smith, Mark D.; Pellechia, Perry J.; Sherrill, C. David; Shimizu, Ken D.; Organic letters 16 (2014) 5064–5067; doi:10.1021/ol502418k

data_1517800
_publ_section_title
;
 The CH-\p Interactions of Methyl Ethers as a Model for
 Carbohydrate-N-Heteroarene Interactions.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5064
_journal_page_last               5067
_journal_paper_doi               10.1021/ol502418k
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C30 H24 N2 O5'
_chemical_formula_sum            'C30 H24 N2 O5'
_chemical_formula_weight         492.51
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-25
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.080(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.233(2)
_cell_length_b                   16.180(3)
_cell_length_c                   9.9786(17)
_cell_measurement_reflns_used    5858
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.40
_cell_volume                     2298.0(7)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0511
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28964
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.344
_diffrn_source_target            Mo
_diffrn_source_voltage           42.0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.852648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0937 before and 0.0403 after correction.
The Ratio of minimum to maximum transmission is 0.8526.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_recrystallization_method 'Slow evap. from CH2Cl2'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+1.7598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                3866
_reflns_number_total             4742
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502418k_si_003.cif
_cod_data_source_block           lpc1s
_cod_depositor_comments
'Adding full bibliography for 1517798--1517800.cif.'
_cod_original_cell_volume        2297.9(7)
_cod_database_code               1517800
_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. Shared sites
{C8A, C8B}
{C9A, C9B}
{C10A, C10B}
{C11A, C11B}
{C12A, C12B}
{C13A, C13B}
{C14A, N2B}
{C15A, C14B}
{C16A, C15B}
{N2A, C16B}
{C17A, C17B}
{C18A, C18B}
{C19A, C19B}
{C20A, C20B}
3. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8B)
Uanis(C9A) = Uanis(C9B)
Uanis(C10A) = Uanis(C10B)
Uanis(C11A) = Uanis(C11B)
Uanis(C12A) = Uanis(C12B)
Uanis(C13A) = Uanis(C13B)
Uanis(C14A) = Uanis(N2B)
Uanis(C15A) = Uanis(C14B)
Uanis(C16A) = Uanis(C15B)
Uanis(N2A) = Uanis(C16B)
Uanis(C17A) = Uanis(C17B)
Uanis(C18A) = Uanis(C18B)
Uanis(C19A) = Uanis(C19B)
Uanis(C20A) = Uanis(C20B)
4. Others
 Sof(C8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=
 Sof(H13B)=Sof(N2B)=Sof(C14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=
 Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=1-FVAR(1)
 Sof(C8A)=Sof(C9A)=Sof(C10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(N2A)=Sof(C17A)=Sof(H17A)=
 Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6)
5.b Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A), C17A(H17A), C18A(H18A),
 C19A(H19A), C11B(H11B), C12B(H12B), C13B(H13B), C16B(H16B), C17B(H17B),
 C18B(H18B), C19B(H19B), C25(H25), C26(H26), C27(H27)
5.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
;