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_1555610
_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, C14 H10, 3(C2 H4 Cl2)'
_chemical_formula_sum            'C74 H61 Cl6 N15 O3'
_chemical_formula_weight         1421.07
_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             2016-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.061(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.154(4)
_cell_length_b                   13.571(3)
_cell_length_c                   31.638(6)
_cell_measurement_reflns_used    6272
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.31
_cell_volume                     6936(3)
_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 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0965
_diffrn_reflns_av_unetI/netI     0.1788
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            67978
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.286
_diffrn_reflns_theta_max         25.286
_diffrn_reflns_theta_min         1.287
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1337 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8796.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0039(7)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     986
_refine_ls_number_reflns         12141
_refine_ls_number_restraints     509
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.2291
_refine_ls_R_factor_gt           0.1040
_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^)+(0.1940P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2792
_refine_ls_wR_factor_ref         0.3517
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5190
_reflns_number_total             12141
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b01554_si_006.cif
_cod_data_source_block           js_200_phen_a
_cod_database_code               1555610
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N14B_1-N13_1 \\sim N14A_1-N13_1
 with sigma of 0.02
 N15B_1-N14B_1 \\sim N15A_1-N14A_1
 with sigma of 0.02
 N15B_1-C52_1 \\sim N15A_1-C52_1
 with sigma of 0.02
 N13_1-C53A_1 \\sim N13_1-C53B_1
 with sigma of 0.02
 C53A_1-C52_1 \\sim C53B_1-C52_1
 with sigma of 0.02
 N14B_1-C53B_1 \\sim N14A_1-C53A_1
 with sigma of 0.04
 N15B_1-C53B_1 \\sim N15A_1-C53A_1
 with sigma of 0.04
 N13_1-N15A_1 \\sim N13_1-N15B_1
 with sigma of 0.04
 C52_1-N14A_1 \\sim C52_1-N14B_1
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N14B_1 \\sim N14A_1 \\sim N15B_1 \\sim N15A_1: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C2_2 \\sim C1_2 \\sim C6_2 \\sim C7_2 \\sim C3_2 \\sim C5_2 \\sim C14_2 \\sim
C8_2 \\sim C12_2 \\sim C4_2 \\sim C13_2 \\sim C9_2 \\sim C11_2 \\sim C10_2:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
N15B_1 \\sim N14B_1 \\sim N13_1 \\sim C53B_1 \\sim C52_1: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
N15A_1 \\sim N14A_1 \\sim N13_1 \\sim C53A_1 \\sim C52_1: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C53A_1 \\sim C53B_1: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08
C2B_4 \\sim C2A_4 \\sim C1A_4 \\sim C1B_4: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl1A_4 \\sim Cl1B_4 \\sim Cl2B_4 \\sim Cl2A_4: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C2B_5 \\sim C1B_5 \\sim C1A_5 \\sim C2A_5: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl1B_5 \\sim Cl1A_5 \\sim Cl2B_5 \\sim Cl2A_5: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C2_2, C1_2, C6_2, C7_2, C3_2, C5_2, C14_2, C8_2, C12_2, C4_2, C13_2, C9_2,
 C11_2, C10_2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1B_4, C2B_4, C1B_4, Cl2B_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A_4, C2A_4, C1A_4, Cl2A_4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2A_5, Cl1A_5, C2A_5, C1A_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl2B_5, Cl1B_5, C2B_5, C1B_5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{Cl1_3, Cl2_3, C1_3, C2_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1A_4, Cl2A_4, C1A_4, C2A_4}
{Cl1_3, Cl2_3, C1_3, C2_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_4, Cl2B_4, C1B_4, C2B_4}
{Cl1_3, Cl2_3, C1_3, C2_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1A_5, Cl2A_5, C1A_5, C2A_5}
{Cl1_3, Cl2_3, C1_3, C2_3} sigma for 1-2: 0.02, 1-3: 0.04
as
{Cl1B_5, Cl2B_5, C1B_5, C2B_5}
6. Others
 Sof(N14B)=Sof(N15B)=Sof(C53B)=Sof(H53B)=1-FVAR(1)
 Sof(N14A)=Sof(N15A)=Sof(C53A)=Sof(H53A)=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), 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)
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), C53A(H53A), C53B(H53B), C2(H2), C3(H3), C4(H4),
 C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14)
;
_shelx_res_checksum              7681
_shelx_hkl_checksum              96190
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'