#------------------------------------------------------------------------------
#$Date: 2020-04-05 13:44:54 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/35/7703502.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7703502
loop_
_publ_author_name
'Ju, Huiyeong'
'Tenma, Honoka'
'Iwase, Miki'
'Lee, Eunji'
'Ikeda, Mari'
'Kuwahara, Shunsuke'
'Habata, Yoichi'
_publ_section_title
;
 Inclusion of alkyl nitriles by tetra-armed cyclens with styrylmethyl
 groups.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3112
_journal_page_last               3119
_journal_paper_doi               10.1039/d0dt00335b
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C48 H60 N4 O4'
_chemical_formula_sum            'C48 H60 N4 O4'
_chemical_formula_weight         757.00
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-24 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                101.209(10)
_cell_angle_beta                 110.101(10)
_cell_angle_gamma                100.626(10)
_cell_formula_units_Z            1
_cell_length_a                   9.370(6)
_cell_length_b                   9.873(6)
_cell_length_c                   12.853(8)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      2.39
_cell_volume                     1053.8(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.1333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12267
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.757
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4634
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0729
_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/[σ²(Fo²)+(0.0804P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.2064
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2582
_reflns_number_total             4141
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00335b2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7703501--7703508.cif.'
_cod_original_cell_volume        1053.8(12)
_cod_database_code               7703502
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7269(2) 0.4764(2) 0.65767(16) 0.0389(5) Uani 1 1 d . . . . .
O2 O 0.1996(2) 0.17812(19) 0.44521(15) 0.0329(5) Uani 1 1 d . . . . .
N1 N 0.6310(3) -0.2399(2) 0.07605(17) 0.0257(5) Uani 1 1 d . . . . .
N2 N 0.2999(3) -0.4557(2) -0.09250(18) 0.0269(5) Uani 1 1 d . . . . .
C1 C 0.7704(3) -0.2737(3) 0.1500(2) 0.0274(6) Uani 1 1 d . . . . .
H1A H 0.8269 -0.1938 0.2217 0.033 Uiso 1 1 calc R U . . .
H1B H 0.8427 -0.2820 0.1097 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5736(3) -0.3203(3) -0.0454(2) 0.0284(6) Uani 1 1 d . . . . .
H2A H 0.5903 -0.4171 -0.0508 0.034 Uiso 1 1 calc R U . . .
H2B H 0.6344 -0.2706 -0.0831 0.034 Uiso 1 1 calc R U . . .
C3 C 0.3995(3) -0.3340(3) -0.1073(2) 0.0306(6) Uani 1 1 d . . . . .
H3A H 0.3759 -0.2445 -0.0769 0.037 Uiso 1 1 calc R U . . .
H3B H 0.3744 -0.3469 -0.1906 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2720(3) -0.5875(3) -0.1811(2) 0.0280(6) Uani 1 1 d . . . . .
H4A H 0.3683 -0.5834 -0.1975 0.034 Uiso 1 1 calc R U . . .
H4B H 0.1854 -0.5900 -0.2529 0.034 Uiso 1 1 calc R U . . .
C5 C 0.6653(3) -0.0844(3) 0.0907(2) 0.0303(6) Uani 1 1 d . . . . .
H5A H 0.5940 -0.0662 0.0208 0.036 Uiso 1 1 calc R U . . .
H5B H 0.7752 -0.0476 0.0983 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6455(3) -0.0045(3) 0.1939(2) 0.0281(6) Uani 1 1 d . . . . .
H6A H 0.5473 -0.0339 0.2006 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7558(3) 0.1044(3) 0.2763(2) 0.0271(6) Uani 1 1 d . . . . .
H7A H 0.8561 0.1255 0.2715 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7414(3) 0.1970(3) 0.3750(2) 0.0264(6) Uani 1 1 d . . . . .
C9 C 0.8756(3) 0.2998(3) 0.4597(2) 0.0292(6) Uani 1 1 d . . . . .
H9A H 0.9748 0.3072 0.4537 0.035 Uiso 1 1 calc R U . . .
C10 C 0.8663(3) 0.3907(3) 0.5520(2) 0.0298(6) Uani 1 1 d . . . . .
H10A H 0.9587 0.4603 0.6083 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7234(3) 0.3813(3) 0.5630(2) 0.0280(6) Uani 1 1 d . . . . .
C12 C 0.5888(3) 0.2813(3) 0.4798(2) 0.0298(6) Uani 1 1 d . . . . .
H12A H 0.4897 0.2748 0.4861 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5991(3) 0.1908(3) 0.3875(2) 0.0296(6) Uani 1 1 d . . . . .
H13A H 0.5060 0.1223 0.3309 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5843(4) 0.4635(3) 0.6765(3) 0.0435(8) Uani 1 1 d . . . . .
H14A H 0.6026 0.5372 0.7464 0.065 Uiso 1 1 calc R U . . .
H14B H 0.5021 0.4761 0.6103 0.065 Uiso 1 1 calc R U . . .
H14C H 0.5502 0.3682 0.6858 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1522(3) -0.4278(3) -0.0916(2) 0.0323(6) Uani 1 1 d . . . . .
H15A H 0.0747 -0.5197 -0.1067 0.039 Uiso 1 1 calc R U . . .
H15B H 0.1079 -0.3835 -0.1540 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1781(3) -0.3303(3) 0.0215(2) 0.0315(6) Uani 1 1 d . . . . .
H16A H 0.2195 -0.3620 0.0882 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1484(3) -0.2034(3) 0.0372(2) 0.0283(6) Uani 1 1 d . . . . .
H17A H 0.1104 -0.1714 -0.0297 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1676(3) -0.1067(3) 0.1465(2) 0.0255(6) Uani 1 1 d . . . . .
C19 C 0.1940(3) -0.1493(3) 0.2474(2) 0.0287(6) Uani 1 1 d . . . . .
H19A H 0.2048 -0.2433 0.2468 0.034 Uiso 1 1 calc R U . . .
C20 C 0.2050(3) -0.0588(3) 0.3482(2) 0.0297(6) Uani 1 1 d . . . . .
H20A H 0.2221 -0.0907 0.4155 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1909(3) 0.0794(3) 0.3502(2) 0.0276(6) Uani 1 1 d . . . . .
C22 C 0.1660(3) 0.1253(3) 0.2514(2) 0.0279(6) Uani 1 1 d . . . . .
H22A H 0.1565 0.2197 0.2524 0.034 Uiso 1 1 calc R U . . .
C23 C 0.1550(3) 0.0328(3) 0.1519(2) 0.0264(6) Uani 1 1 d . . . . .
H23A H 0.1383 0.0652 0.0848 0.032 Uiso 1 1 calc R U . . .
C24 C 0.2269(4) 0.1347(3) 0.5483(2) 0.0412(8) Uani 1 1 d . . . . .
H24A H 0.2307 0.2135 0.6097 0.062 Uiso 1 1 calc R U . . .
H24B H 0.1412 0.0508 0.5343 0.062 Uiso 1 1 calc R U . . .
H24C H 0.3277 0.1099 0.5719 0.062 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C14 117.6(2) . . ?
C21 O2 C24 117.0(2) . . ?
C2 N1 C1 113.08(19) . . ?
C2 N1 C5 111.39(19) . . ?
C1 N1 C5 109.6(2) . . ?
C15 N2 C3 111.6(2) . . ?
C15 N2 C4 112.0(2) . . ?
C3 N2 C4 110.2(2) . . ?
N1 C1 C4 112.5(2) . 2_645 ?
N1 C2 C3 110.9(2) . . ?
N2 C3 C2 111.6(2) . . ?
N2 C4 C1 115.1(2) . 2_645 ?
N1 C5 C6 112.7(2) . . ?
C7 C6 C5 124.0(3) . . ?
C6 C7 C8 127.5(3) . . ?
C13 C8 C9 117.2(2) . . ?
C13 C8 C7 123.4(2) . . ?
C9 C8 C7 119.4(2) . . ?
C10 C9 C8 121.1(3) . . ?
C9 C10 C11 120.5(3) . . ?
O1 C11 C10 115.9(2) . . ?
O1 C11 C12 124.6(2) . . ?
C10 C11 C12 119.5(2) . . ?
C11 C12 C13 119.6(3) . . ?
C12 C13 C8 122.0(3) . . ?
N2 C15 C16 111.2(2) . . ?
C17 C16 C15 125.7(3) . . ?
C16 C17 C18 127.3(2) . . ?
C23 C18 C19 117.1(2) . . ?
C23 C18 C17 120.2(2) . . ?
C19 C18 C17 122.7(2) . . ?
C20 C19 C18 121.9(2) . . ?
C19 C20 C21 119.4(2) . . ?
O2 C21 C22 115.6(2) . . ?
O2 C21 C20 124.4(2) . . ?
C22 C21 C20 120.0(2) . . ?
C23 C22 C21 119.5(2) . . ?
C22 C23 C18 122.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.371(3) . ?
O1 C14 1.425(4) . ?
O2 C21 1.374(3) . ?
O2 C24 1.426(3) . ?
N1 C2 1.463(3) . ?
N1 C1 1.466(3) . ?
N1 C5 1.469(3) . ?
N2 C15 1.464(3) . ?
N2 C3 1.466(3) . ?
N2 C4 1.467(3) . ?
C1 C4 1.523(3) 2_645 ?
C2 C3 1.516(4) . ?
C4 C1 1.523(3) 2_645 ?
C5 C6 1.495(3) . ?
C6 C7 1.319(4) . ?
C7 C8 1.474(3) . ?
C8 C13 1.389(4) . ?
C8 C9 1.398(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.384(3) . ?
C15 C16 1.492(3) . ?
C16 C17 1.326(4) . ?
C17 C18 1.469(3) . ?
C18 C23 1.394(3) . ?
C18 C19 1.397(3) . ?
C19 C20 1.382(3) . ?
C20 C21 1.391(4) . ?
C21 C22 1.389(4) . ?
C22 C23 1.379(3) . ?
