Synthesis and Structural Characterization of a Cyclen-Derived Molecular Cage.
Ganss, Alexander; Belda, Raquel; Pitarch, Javier; Goddard, Richard; García-España, Enrique; Kubik, Stefan; Organic letters 17 (2015) 5850–5853; doi:10.1021/acs.orglett.5b03027

data_1555442
_publ_section_title
;
 Synthesis and Structural Characterization of a Cyclen-Derived Molecular
 Cage.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              5850
_journal_page_last               5853
_journal_paper_doi               10.1021/acs.orglett.5b03027
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C104 H152 Cl2 Cu2 N16 O8, 6(Cl), 9(H2 O)'
_chemical_formula_sum            'C104 H170 Cl8 Cu2 N16 O17'
_chemical_formula_weight         2327.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.806(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.299(2)
_cell_length_b                   19.2324(13)
_cell_length_c                   28.254(4)
_cell_measurement_reflns_used    3982
_cell_measurement_temperature    120(10)
_cell_measurement_theta_max      20.9930
_cell_measurement_theta_min      3.3350
_cell_volume                     13740(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 16.0267
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'SuperNova, Single source at offset, Sapphire3'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0978
_diffrn_reflns_av_unetI/netI     0.1388
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28875
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.044
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_description       block
_exptl_crystal_F_000             4944
_exptl_crystal_size_max          0.2749
_exptl_crystal_size_mid          0.2541
_exptl_crystal_size_min          0.1514
_platon_squeeze_details
;
Diffuse, disordered solvent molecules could not be adequately modeled.
The bypass procedure Squeeze from Platon software was used to remove 
the electronic contribution from these solvents. The total potential 
solvent accessible void volume
was 2728 Ang^3^ and the electron count / cell = 572. As the exact 
solvent content is not known, the reported formula reflects only 
the atoms used in the refinement.
;
_refine_diff_density_max         1.380
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         12024
_refine_ls_number_restraints     113
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1702
_refine_ls_R_factor_gt           0.1148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1879P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2927
_refine_ls_wR_factor_ref         0.3454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5280
_reflns_number_total             12024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03027_si_004.cif
_cod_data_source_block           CRYSTALCu2L6
_cod_database_code               1555442
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups, All
  O(H) groups, All O(H,H) groups
2. Restrained distances
 C20A-C19
 1.51 with sigma of 0.02
 C22-O2A
 2.1 with sigma of 0.02
 C20A-C21A
 2.38 with sigma of 0.01
 C22-C21A
 1.54 with sigma of 0.02
 C20A-O2A
 1.5 with sigma of 0.02
 C1-C2
 1.46 with sigma of 0.01
 C21B-O2B
 1.5 with sigma of 0.02
 H7-N7
 0.97 with sigma of 0.02
 N7-H6E
 2.1 with sigma of 0.02
 O7-H7C
 0.82 with sigma of 0.02
 H5D-O5
 0.82 with sigma of 0.02
 O5-H5C
 0.82 with sigma of 0.02
 H6E-O6
 0.82 with sigma of 0.02
 O6-H6F
 0.82 with sigma of 0.02
 N5-H5
 0.89 with sigma of 0.02
 H6B-N6
 0.9 with sigma of 0.02
 H9C-O9
 0.85 with sigma of 0.01
 H9D-O9
 0.82 with sigma of 0.02
 H11A-O11
 0.82 with sigma of 0.02
 O11-H11B
 0.82 with sigma of 0.02
 H11B-H11A
 1.3 with sigma of 0.02
3. Rigid bond restraints
 O2A, C20A, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O1, C19
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 C21A, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2A, C21A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N1, C8, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C30, N3, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4, C3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C21B, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C19, C20B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C46, C47
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C35, C34
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C16
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C23, N6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C24, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5 \\sim N3 \\sim C6: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.01
C19 \\sim O1: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
C21B \\sim C22: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.01
Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(C20A) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C21A) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.01
Uanis(C39) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.2
Uanis(C31) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C38) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C20B) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: H19A(0.5) H19B(0.5) H22A(0.5) H22B(0.5) C20A(0.5) H20A(0.5)
 H20B(0.5) C21A(0.5) H21A(0.5) H21B(0.5) O2A(0.5) O2B(0.5) C21B(0.5) H21C(0.5)
 H21D(0.5) C20B(0.5) H20C(0.5) H20D(0.5)
6.a Rotating group with stretchable bonds:
 N7(H7), N5(H5), O6(H6E,H6F), O7(H7C), O5(H5C,H5D), O11(H11A,H11B), O9(H9C,H9D)
6.b Secondary CH2 refined with riding coordinates:
 N8(H8A,H8B), C9(H9A,H9B), C45(H45A,H45B), C38(H38A,H38B), N6(H6A,H6B),
 C42(H42A,H42B), C31(H31A,H31B), C30(H30A,H30B), C041(H04A,H04B), C52(H52A,
 H52B), C3(H3A,H3B), C44(H44A,H44B), C8(H8C,H8D), C2(H2A,H2B), C43(H43A,H43B),
 C7(H7A,H7B), C4(H4A,H4B), C23(H23A,H23B), C40(H40A,H40B), C16(H16A,H16B),
 C39(H39A,H39B), C18(H18A,H18B), C6(H6C,H6D), C1(H1A,H1B), C17(H17A,H17B),
 C5(H5A,H5B), C19(H19A,H19B), C22(H22A,H22B), C20A(H20A,H20B), C21A(H21A,H21B),
 C21B(H21C,H21D), C20B(H20C,H20D)
6.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C47(H47), C50(H50), C33(H33), C37(H37), C51(H51), C11(H11),
 C15(H15), C26(H26), C48(H48), C29(H29), C12(H12), C28(H28), C34(H34), C25(H25),
  C14(H14)
;