Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic Hydrocarbons.
Samanta, Jayanta; Natarajan, Ramalingam; Organic letters 18 (2016) 3394–3397; doi:10.1021/acs.orglett.6b01554

data_1555609
_publ_section_title
;
 Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic
 Hydrocarbons.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3394
_journal_page_last               3397
_journal_paper_doi               10.1021/acs.orglett.6b01554
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
'C54 H39 N15 O3, 1.18(C2 H4 Cl2), 3.82(C5 H4)'
_chemical_formula_sum            'C75.47 H59 Cl2.36 N15 O3'
_chemical_formula_weight         1307.47
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.909(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7998(10)
_cell_length_b                   20.2414(19)
_cell_length_c                   29.845(3)
_cell_measurement_reflns_used    9610
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.26
_cell_volume                     6520.6(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_unetI/netI     0.1116
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            103965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.731
_diffrn_reflns_theta_min         1.696
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1759 before and 0.0934 after correction.
The Ratio of minimum to maximum transmission is 0.7175.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             2723
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         2.281
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       0.0013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     920
_refine_ls_number_reflns         14979
_refine_ls_number_restraints     585
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.2334
_refine_ls_R_factor_gt           0.1317
_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^)+(0.1610P)^2^+26.7716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3508
_refine_ls_wR_factor_ref         0.4114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6887
_reflns_number_total             14979
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_004.cif
_cod_data_source_block           rn_js200_np_0m_a
_cod_original_cell_volume        6520.6(10)
_cod_database_code               1555609
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C1B_3-C2B_3
 1.54 with sigma of 0.04
 Cl2_3-C1B_3 = Cl1_3-C2B_3
 1.74 with sigma of 0.04
 H3A_5-H21_1
 -1.9 with sigma of 0.04
 C2_3-C1_3 \\sim C3_3-C2_3 \\sim C4_3-C3_3 \\sim C5_3-C4_3
 with sigma of 0.02
 O3A_1-C50A_1 \\sim O3_1-C50_1
 with sigma of 0.02
 C6_5-C1_5 \\sim C2_5-C1_5 \\sim C3_5-C2_5 \\sim C4_5-C3_5 \\sim C5_5-C4_5
\\sim C6_5-C5_5 \\sim C7_5-
 C6_5 \\sim C8_5-C7_5 \\sim C9_5-C8_5 \\sim C9_5-C10_5 \\sim C5_5-C10_5
 with sigma of 0.02
 C1_5-C3_5 \\sim C2_5-C4_5 \\sim C3_5-C5_5 \\sim C4_5-C6_5 \\sim C5_5-C7_5
\\sim C6_5-C8_5 \\sim C7_5-
 C9_5 \\sim C8_5-C10_5 \\sim C9_5-C5_5 \\sim C10_5-C6_5
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C2_5 \\sim C5_5 \\sim C1_5 \\sim C4_5 \\sim C10_5 \\sim C3_5 \\sim C9_5 \\sim
C7_5: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C1_5 \\sim C5_5 \\sim C4_5 \\sim C6_5 \\sim C2_5 \\sim C10_5 \\sim C3_5 \\sim
C7_5 \\sim C9_5: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C10_1 \\sim C11_1 \\sim C11A_1 \\sim C12_1 \\sim C12A_1 \\sim C13_1 \\sim
C13A_1 \\sim C14_1 \\sim C14A_1 \\sim C15_1 \\sim C15A_1 \\sim O3_1 \\sim O3A_1
\\sim C50A_1 \\sim C50_1 \\sim C49_1: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C50A_1 \\sim C50_1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C1_3 \\sim C2_3 \\sim C3_3 \\sim C4_3 \\sim C5_3: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
Cl2_3 \\sim C1B_3 \\sim C2B_3 \\sim Cl1_3: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C5_3 \\sim C1_3 \\sim C2_3 \\sim C3_3 \\sim C4_3: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(C1_5) = Uanis(C2_5) = Uanis(C6_5) = Uanis(C3_5) = Uanis(C5_5) =
Uanis(C7_5) = Uanis(C4_5) = Uanis(C10_5) = Uanis(C8_5) = Uanis(C9_5) =
Uanis(C1A_5) = Uanis(C2A_5) = Uanis(C6A_5) = Uanis(C3A_5) = Uanis(C5A_5) =
Uanis(C7A_5) = Uanis(C4A_5) = Uanis(C10A_5) = Uanis(C8A_5) = Uanis(C9A_5)
4. Rigid body (RIGU) restrains
 C10_1, C11_1, C12_1, C13_1, C14_1, C15_1, O3_1, C50_1, C49_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10_1, C11A_1, C12A_1, C13A_1, C14A_1, C15A_1, O3A_1, C50A_1, C49_1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2_3, C1B_3, C2B_3, Cl1_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C5_3, C1_3, C2_3, C3_3, C4_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 FVAR(1)
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=
 Sof(C15A)=Sof(H15A)=Sof(C50A)=Sof(H50C)=Sof(H50D)=Sof(O3A)=1-FVAR(2)
 Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=
 Sof(H15)=Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(O3)=FVAR(2)
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(Cl1)=Sof(Cl2)=1-
 FVAR(3)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B), C50(H50A,H50B), C50A(H50C,
 H50D), C51(H51A,H51B), C54(H54A,H54B), C1(H1A,H1B), C2(H2A,H2B), C1B(H1BA,
 H1BB), C2B(H2BA,H2BB)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), C17(H17), C18(H18), C20(H20),
 C21(H21), C26(H26), C27(H27), C29(H29), C30(H30), C33(H33), C35(H35), C32(H32),
  C36(H36), C38(H38), C39(H39), C41(H41), C42(H42), C44(H44), C48(H48),
 C52(H52), C1(H1), C3(H3), C4(H4), C5(H5), C1(H1), C2(H2), C3(H3), C4(H4),
 C7(H7), C8(H8), C9(H9), C10(H10), C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A),
 C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C1(H1), C2(H2), C3(H3), C5(H5)
6.c Naphthalene refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A,C7A,C8A,C9A,C10A)
;
_shelx_res_checksum              36988
_shelx_hkl_checksum              30819
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'