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_1555612
_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(C20 H12), 3(C2 H4 Cl2)'
_chemical_formula_sum            'C80 H63 Cl6 N15 O3'
_chemical_formula_weight         1495.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.389(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1736(17)
_cell_length_b                   13.7072(16)
_cell_length_c                   31.887(3)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    100
_cell_measurement_theta_max      20.70
_cell_measurement_theta_min      2.25
_cell_volume                     7063.0(13)
_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 0.949
_diffrn_measured_fraction_theta_max 0.949
_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  0.1512
_diffrn_reflns_av_unetI/netI     0.2526
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            69263
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.166
_diffrn_reflns_theta_max         25.166
_diffrn_reflns_theta_min         1.278
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.307
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1222 before and 0.0745 after correction.
The Ratio of minimum to maximum transmission is 0.8800.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1257
_refine_ls_number_reflns         12050
_refine_ls_number_restraints     2105
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.3066
_refine_ls_R_factor_gt           0.1179
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2958
_refine_ls_wR_factor_ref         0.4008
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3997
_reflns_number_total             12050
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_011.cif
_cod_data_source_block           rn_js_200_r_bzpy_0m
_cod_original_cell_volume        7063.1(13)
_cod_database_code               1555612
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2A_2-C1A_2 = C2B_2-C1B_2
 1.54 with sigma of 0.02
 C2A_4-C1A_4 = C1B_4-C2B_4
 1.54 with sigma of 0.04
 Cl1A_4-C1A_4 = Cl2A_4-C2A_4 = Cl1B_4-C1B_4 = Cl2B_4-C2B_4
 1.8 with sigma of 0.04
 Cl1A_4-C2A_4 = C1A_4-Cl2A_4 = Cl1B_4-C2B_4 = C1B_4-Cl2B_4
 3 with sigma of 0.04
 C19_3-C17_3 = C20_3-C5_3 = C6_3-C7_3 = C3_3-C10_3 = C15_3-C13_3
 2.5 with sigma of 0.04
 C18B_3-C20B_3 = C15B_3-C11B_3 = C13B_3-C6B_3 = C7B_3-C2B_3
 2.5 with sigma of 0.04
 C2B_5-C1B_5
 1.54 with sigma of 0.04
 C2A_5-C1A_5
 1.54 with sigma of 0.04
 Cl1B_5-C1B_5 = Cl2B_5-C2B_5
 1.7 with sigma of 0.04
 Cl1A_5-C1A_5 = Cl2A_5-C2A_5
 1.7 with sigma of 0.04
 C2B_5-Cl1B_5 = C1B_5-Cl2B_5
 3 with sigma of 0.04
 C2A_5-Cl1A_5 = C1A_5-Cl2A_5
 3 with sigma of 0.04
 C2_3-C1_3 \\sim C3_3-C2_3 \\sim C4_3-C3_3 \\sim C5_3-C4_3 \\sim C6_3-C5_3
\\sim C6_3-C1_3 \\sim C4_3-
 C10_3 \\sim C9_3-C10_3 \\sim C9_3-C8_3 \\sim C8_3-C7_3 \\sim C7_3-C5_3 \\sim
C7_3-C20_3 \\sim C20_3-
 C19_3 \\sim C19_3-C18_3 \\sim C18_3-C11_3 \\sim C8_3-C11_3 \\sim C12_3-C11_3
\\sim C13_3-C12_3 ~
 C14_3-C13_3 \\sim C9_3-C14_3 \\sim C15_3-C12_3 \\sim C16_3-C15_3 \\sim
C17_3-C16_3 \\sim C18_3-
 C17_3
 with sigma of 0.02
 C2_3-C4_3 \\sim C1_3-C5_3 \\sim C3_3-C1_3 \\sim C4_3-C6_3 \\sim C4_3-C9_3
\\sim C5_3-C8_3 \\sim C10_3-
 C5_3 \\sim C9_3-C7_3 \\sim C9_3-C13_3 \\sim C8_3-C12_3 \\sim C14_3-C8_3 \\sim
C13_3-C11_3 \\sim C7_3-
 C11_3 \\sim C20_3-C18_3 \\sim C8_3-C20_3 \\sim C11_3-C19_3 \\sim C11_3-C15_3
\\sim C18_3-C16_3 ~
 C12_3-C18_3 \\sim C15_3-C17_3
 with sigma of 0.04
 C2B_3-C1B_3 \\sim C3B_3-C2B_3 \\sim C4B_3-C3B_3 \\sim C5B_3-C4B_3 \\sim
C6B_3-C5B_3 \\sim C6B_3-
 C1B_3 \\sim C7B_3-C3B_3 \\sim C8B_3-C7B_3 \\sim C9B_3-C8B_3 \\sim C9B_3-C10B_3
\\sim C4B_3-C10B_3
 \\sim C5B_3-C13B_3 \\sim C13B_3-C12B_3 \\sim C12B_3-C11B_3 \\sim C11B_3-C10B_3
\\sim C9B_3-C20B_3
 \\sim C20B_3-C19B_3 \\sim C19B_3-C14B_3 \\sim C14B_3-C11B_3 \\sim
C15B_3-C14B_3 \\sim C16B_3-
 C15B_3 \\sim C17B_3-C16B_3 \\sim C18B_3-C17B_3 \\sim C19B_3-C18B_3
 with sigma of 0.02
 C1B_3-C3B_3 \\sim C6B_3-C4B_3 \\sim C2B_3-C6B_3 \\sim C3B_3-C5B_3 \\sim
C3B_3-C8B_3 \\sim C4B_3-
 C9B_3 \\sim C7B_3-C4B_3 \\sim C8B_3-C10B_3 \\sim C5B_3-C10B_3 \\sim
C13B_3-C11B_3 \\sim C4B_3-
 C13B_3 \\sim C10B_3-C12B_3 \\sim C10B_3-C20B_3 \\sim C11B_3-C19B_3 \\sim
C9B_3-C11B_3 \\sim C20B_3-
 C14B_3 \\sim C14B_3-C18B_3 \\sim C15B_3-C17B_3 \\sim C19B_3-C15B_3 \\sim
C18B_3-C16B_3
 with sigma of 0.04
 N13_1-C42B_1 \\sim N13_1-C42_1
 with sigma of 0.04
 C43_1-C42B_1 \\sim C43_1-C42_1
 with sigma of 0.04
 N14_1-N13_1 \\sim N14B_1-N13_1
 with sigma of 0.04
 N15_1-C43_1 \\sim N15B_1-C43_1
 with sigma of 0.04
 Cl2B_2-C2B_2 \\sim Cl2A_2-C2A_2 \\sim Cl1A_2-C1A_2 \\sim Cl1B_2-C1B_2
 with sigma of 0.02
 C1B_2-Cl2B_2 \\sim C2B_2-Cl1B_2 \\sim C2A_2-Cl1A_2 \\sim C1A_2-Cl2A_2
 with sigma of 0.04
 C42B_1-N15_1 \\sim C42_1-N15B_1
 with sigma of 0.04
 C42B_1-N14_1 \\sim C42_1-N14B_1
 with sigma of 0.04
 C43_1-C14_1 \\sim C14_1-C43_1
 with sigma of 0.04
 N13_1-N15_1 \\sim N13_1-N15B_1
 with sigma of 0.04
3. Restrained planarity
 C17B_3, C1B_3, C2B_3, C6B_3, C3B_3, C5B_3, C4B_3, C7B_3, C13B_3, C10B_3,
 C8B_3, C12B_3, C9B_3, C11B_3, C20B_3, C14B_3, C19B_3, C15B_3, C18B_3, C16B_3
 with sigma of 0.04
 C16_3, C1_3, C2_3, C6_3, C3_3, C5_3, C4_3, C7_3, C10_3, C8_3, C20_3, C9_3,
 C11_3, C19_3, C14_3, C12_3, C18_3, C13_3, C15_3, C17_3
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C1_3 \\sim C2_3 \\sim C3_3 \\sim C4_3 \\sim C5_3 \\sim C6_3 \\sim C7_3 \\sim
C8_3 \\sim C9_3 \\sim C10_3 \\sim C11_3 \\sim C12_3 \\sim C13_3 \\sim C14_3
\\sim C15_3 \\sim C16_3 \\sim C17_3 \\sim C18_3 \\sim C19_3 \\sim C20_3: within
2A with sigma of 0.02 and sigma for terminal atoms of 0.04
C1B_3 \\sim C2B_3 \\sim C3B_3 \\sim C4B_3 \\sim C5B_3 \\sim C6B_3 \\sim C7B_3
\\sim C8B_3 \\sim C9B_3 \\sim C10B_3 \\sim C11B_3 \\sim C12B_3 \\sim C13B_3
\\sim C14B_3 \\sim C15B_3 \\sim C16B_3 \\sim C17B_3 \\sim C18B_3 \\sim C19B_3
\\sim C20B_3: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Cl2A_2 \\sim C1A_2 \\sim C2A_2 \\sim Cl1A_2 \\sim Cl2B_2 \\sim C1B_2 \\sim
C2B_2 \\sim Cl1B_2: within 1.8A with sigma of 0.02 and sigma for terminal atoms
of 0.04
Cl1B_4 \\sim C2B_4 \\sim Cl2B_4 \\sim C1B_4 \\sim Cl2A_4 \\sim C2A_4 \\sim
C1A_4 \\sim Cl1A_4: within 1.8A with sigma of 0.02 and sigma for terminal atoms
of 0.04
C43_1 \\sim C42B_1 \\sim C42_1 \\sim N13_1 \\sim N14B_1 \\sim N15B_1 \\sim
N14_1 \\sim N15_1: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04
Cl1B_5 \\sim Cl2B_5 \\sim C2B_5 \\sim C1B_5 \\sim Cl1A_5 \\sim C1A_5 \\sim
C2A_5 \\sim Cl2A_5: within 1.8A with sigma of 0.02 and sigma for terminal atoms
of 0.04
5. Rigid body (RIGU) restrains
 C1_3, C2_3, C3_3, C4_3, C5_3, C6_3, C7_3, C8_3, C9_3, C10_3, C11_3, C12_3,
 C13_3, C14_3, C15_3, C16_3, C17_3, C18_3, C19_3, C20_3
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C1B_3, C2B_3, C3B_3, C4B_3, C5B_3, C6B_3, C7B_3, C8B_3, C9B_3, C10B_3, C11B_3,
  C12B_3, C13B_3, C14B_3, C15B_3, C16B_3, C17B_3, C18B_3, C19B_3, C20B_3
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 Cl2B_2, C1B_2, C2B_2, Cl1B_2, Cl2A_2, C1A_2, C2A_2, Cl1A_2
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 Cl2A_4, C2A_4, C1A_4, Cl1A_4, Cl2B_4, C2B_4, C1B_4, Cl1B_4
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 C43_1, C42B_1, C42_1, N13_1, N14B_1, N15B_1, N14_1, N15_1
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 Cl1B_5, Cl2B_5, C2B_5, C1B_5, Cl1A_5, C1A_5, C2A_5, Cl2A_5
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
6. Others
 Sof(N14B)=Sof(N15B)=Sof(C42B)=Sof(H42B)=1-FVAR(1)
 Sof(N14)=Sof(N15)=Sof(C42)=Sof(H42)=FVAR(1)
 Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(C4B)=Sof(C5B)=Sof(C6B)=
 Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(C10B)=Sof(C11B)=
 Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=Sof(C15B)=Sof(H15B)=
 Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=
 Sof(C20B)=Sof(H20B)=1-FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(C17)=
 Sof(H17)=Sof(C18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=FVAR(2)
 Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(Cl1B)=Sof(Cl2B)=
 1-FVAR(3)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(Cl1A)=Sof(Cl2A)=
 FVAR(3)
 Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(Cl1B)=
 1-FVAR(4)
 Sof(Cl2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(Cl1A)=
 FVAR(4)
 Sof(Cl2B)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(Cl1B)=
 1-FVAR(5)
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(Cl2A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(Cl1A)=
 FVAR(5)
7.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C34(H34A,H34B), C41(H41A,H41B), C44(H44A,H44B), C51(H51A,
 H51B), C54(H54A,H54B), C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB),
 C2B(H2BA,H2BB), C2A(H2AA,H2AB), C1A(H1AA,H1AB), C2B(H2BA,H2BB), C1B(H1BA,H1BB),
  C1A(H1AA,H1AB), C2A(H2AA,H2AB), C2B(H2BA,H2BB), C1B(H1BA,H1BB)
7.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18), C20(H20), C21(H21), C26(H26), C27(H27), C29(H29), C30(H30),
  C32(H32), C36(H36), C37(H37), C39(H39), C40(H40), C46(H46), C47(H47),
 C49(H49), C50(H50), C52(H52), C42(H42), C42B(H42B), C1(H1), C2(H2), C3(H3),
 C6(H6), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C1B(H1B), C2B(H2B), C6B(H6B), C7B(H7B), C8B(H8B), C12B(H12B),
 C13B(H13B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B), C20B(H20B)
;
_shelx_res_checksum              94238
_shelx_hkl_checksum              59032
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'