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_1555605
_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, C18 H12, 2(C2 H4 Cl2)'
_chemical_formula_sum            'C76 H59 Cl4 N15 O3'
_chemical_formula_weight         1372.18
_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
_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                 102.091(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.7889(16)
_cell_length_b                   21.013(2)
_cell_length_c                   37.032(3)
_cell_measurement_reflns_used    9460
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.38
_cell_volume                     13535(2)
_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      293.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.0886
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            181530
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         1.120
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1069 before and 0.0738 after correction.
The Ratio of minimum to maximum transmission is 0.8243.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       block
_exptl_crystal_F_000             5696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.722
_refine_diff_density_min         -1.359
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1720
_refine_ls_number_reflns         30814
_refine_ls_number_restraints     671
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1981
_refine_ls_R_factor_gt           0.1277
_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^)+(0.1899P)^2^+48.9122P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3335
_refine_ls_wR_factor_ref         0.3892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17242
_reflns_number_total             30814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_010.cif
_cod_data_source_block           rn_js_200_bzphen_0m_a
_cod_database_code               1555605
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 H17_3-H8_3
 -2.2 with sigma of 0.04
 C2_3-C1_3 = C3_3-C2_3 = C4_3-C3_3 = C5_3-C4_3 = C6_3-C5_3 = C6_3-C1_3 = C7_3-
 C6_3 = C8_3-C7_3 = C9_3-C8_3 = C9_3-C10_3 = C10_3-C1_3 = C11_3-C10_3 = C12_3-
 C11_3 = C13_3-C12_3 = C18_3-C13_3 = C9_3-C18_3 = C18_3-C17_3 = C17_3-C16_3 =
 C16_3-C15_3 = C15_3-C14_3 = C14_3-C13_3
 1.38 with sigma of 0.04
 C2B_6-C1B_6 \\sim C2A_6-C1A_6
 with sigma of 0.02
 Cl1B_6-C1B_6 \\sim Cl1A_6-C1A_6 \\sim Cl2A_6-C2A_6 \\sim Cl2B_6-C2B_6
 with sigma of 0.02
 C2A_6-Cl1A_6 \\sim C1A_6-Cl2A_6 \\sim C2B_6-Cl1B_6 \\sim C1B_6-Cl2B_6
 with sigma of 0.04
 C2A_8-C1A_8 \\sim C2B_8-C1B_8
 with sigma of 0.02
 Cl2A_8-C2A_8 \\sim Cl1A_8-C1A_8 \\sim Cl1B_8-C1B_8 \\sim Cl2B_8-C2B_8
 with sigma of 0.02
 Cl2B_8-C1B_8 \\sim C2B_8-Cl1B_8 \\sim Cl1A_8-C2A_8 \\sim C1A_8-Cl2A_8
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Cl2A_6 \\sim Cl1A_6 \\sim C1A_6 \\sim C2A_6 \\sim Cl2B_6 \\sim Cl1B_6 \\sim
C1B_6 \\sim C2B_6: within 2A with sigma of 0.04 and sigma for terminal atoms of
0.08
C1_4 \\sim C14_4 \\sim C5_4 \\sim C9_4 \\sim C2_4 \\sim C4_4 \\sim C6_4 \\sim
C8_4 \\sim C10_4 \\sim C3_4 \\sim C7_4 \\sim C13_4 \\sim C11_4 \\sim C12_4
\\sim C18_4 \\sim C15_4 \\sim C17_4 \\sim C16_4: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08
Cl1A_8 \\sim Cl2A_8 \\sim Cl1B_8 \\sim Cl2B_8: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(C1A_8) = Uanis(C2A_8) = Uanis(C1B_8) = Uanis(C2B_8)
Uanis(C1A_7) = Uanis(C2A_7) = Uanis(C1B_7) = Uanis(C2B_7)
Uanis(Cl1B_7) = Uanis(Cl2B_7) = Uanis(Cl1A_7) = Uanis(Cl2A_7)
Uanis(C1_3) = Uanis(C2_3) = Uanis(C6_3) = Uanis(C10_3) = Uanis(C3_3) =
Uanis(C5_3) = Uanis(C7_3) = Uanis(C9_3) = Uanis(C11_3) = Uanis(C4_3) =
Uanis(C8_3) = Uanis(C18_3) = Uanis(C12_3) = Uanis(C13_3) = Uanis(C17_3) =
Uanis(C14_3) = Uanis(C16_3) = Uanis(C15_3)
4. Rigid body (RIGU) restrains
 Cl2A_6, Cl1A_6, C1A_6, C2A_6, Cl2B_6, Cl1B_6, C1B_6, C2B_6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_4, C14_4, C5_4, C9_4, C2_4, C4_4, C6_4, C8_4, C10_4, C3_4, C7_4, C13_4,
 C11_4, C12_4, C18_4, C15_4, C17_4, C16_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A_7, Cl2A_7, C1A_7, C2A_7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1B_7, Cl2B_7, C1B_7, C2B_7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A_8, Cl2A_8, C1A_8, C2A_8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1B_8, Cl2B_8, C1B_8, C2B_8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C1_3, C2_3, C6_3, C10_3, C3_3, C5_3, C7_3, C9_3, C11_3, C4_3, C8_3, C18_3,
 C12_3, C13_3, C17_3, C14_3, C16_3, C15_3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{Cl1_5, Cl2_5, C1_5, C2_5} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_7, Cl2B_7, C1B_7, C2B_7}
6. Others
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(1)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(2)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(2)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 1-FVAR(3)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=
 FVAR(3)
7.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,
 H51B), C54(H54A,H54B), C43(H43A,H43B), C46(H46A,H46B), C47(H47A,H47B),
 C50(H50A,H50B), C51(H51A,H51B), C54(H54A,H54B), C1(H1A,H1B), C2(H2A,H2B),
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C1A(H1AA,H1AB),
  C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C1A(H1AA,H1AB), C2A(H2AA,
 H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB)
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), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39), C41(H41),
 C42(H42), C45(H45), C49(H49), C53(H53), 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), C33(H33), C35(H35),
 C36(H36), C38(H38), C39(H39), C41(H41), C42(H42), C45(H45), C49(H49), C53(H53),
  C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C7(H7),
 C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              92158
_shelx_hkl_checksum              75391
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'