#------------------------------------------------------------------------------
#$Date: 2019-02-20 05:31:34 +0200 (Wed, 20 Feb 2019) $
#$Revision: 213722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/15/2021523.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021523
loop_
_publ_author_name
'Raju, Saravanan'
'Butcher, Ray J.'
'Singh, Harkesh B.'
_publ_section_title
;
 Isolation and structure of an 18-membered macrocycle containing two
 diselenide linkages and its precursor
;
_journal_coeditor_code           FN3298
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619002341
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C36 H34 N4 O6 Se4'
_chemical_formula_moiety         'C36 H34 N4 O6 Se4'
_chemical_formula_sum            'C36 H34 N4 O6 Se4'
_chemical_formula_weight         934.51
_chemical_name_systematic
'10,27-Di-tert-butyl 11,28-dioxo-2,3,19,20-tetraselena-10,12,27,29-tetraazapentacyclo[28.4.0.0^4,9^.0^13,18^.0^21,26^]tetratriaconta-1(30),4(9),5,7,13,15,17,21,23,25,31,33-dodecaene-10,27-dicarboxylate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                101.000(2)
_cell_angle_beta                 108.394(2)
_cell_angle_gamma                105.264(2)
_cell_formula_units_Z            1
_cell_length_a                   9.4865(3)
_cell_length_b                   9.7410(2)
_cell_length_c                   11.2789(3)
_cell_measurement_reflns_used    15479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2870
_cell_measurement_theta_min      2.3910
_cell_volume                     910.42(5)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Rigaku CCD dual source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.185
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_description       needle
_exptl_crystal_F_000             462
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.468
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0258
_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/[σ²(Fo²)+(0.0337P)²+0.3223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0651
_reflns_number_gt                4766
_reflns_number_total             5406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            fn3298sup1.cif
_cod_data_source_block           4
_cod_original_cell_volume        910.42(4)
_cod_database_code               2021523
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Se Se1 0.04380(2) 0.49656(2) 0.30624(2) 0.02120(5) Uani d 1
Se Se2 0.20175(2) 0.43386(2) 0.47712(2) 0.02078(5) Uani d 1
O O1 0.62718(14) 0.68582(15) 0.30763(12) 0.0268(3) Uani d 1
O O2 0.39283(14) 0.78120(14) 0.54761(12) 0.0245(3) Uani d 1
O O3 0.63606(14) 0.85044(14) 0.70736(11) 0.0236(2) Uani d 1
N N1 0.38224(16) 0.65545(16) 0.31384(14) 0.0212(3) Uani d 1
H H1 0.341(3) 0.677(2) 0.364(2) 0.028(6) Uiso d 1
N N2 0.61486(15) 0.79034(15) 0.50056(13) 0.0188(3) Uani d 1
C C1 0.13119(19) 0.46199(18) 0.17561(16) 0.0206(3) Uani d 1
C C2 0.0308(2) 0.3550(2) 0.05685(18) 0.0254(3) Uani d 1
H H2 -0.070(2) 0.298(2) 0.052(2) 0.025(5) Uiso d 1
C C3 0.0783(2) 0.3337(2) -0.04709(18) 0.0292(4) Uani d 1
H H3 0.006(3) 0.266(3) -0.126(2) 0.038(6) Uiso d 1
C C4 0.2278(2) 0.4198(2) -0.03280(18) 0.0289(4) Uani d 1
H H4 0.257(3) 0.413(2) -0.099(2) 0.029(6) Uiso d 1
C C5 0.3309(2) 0.5270(2) 0.08602(18) 0.0254(3) Uani d 1
H H5 0.427(3) 0.587(2) 0.095(2) 0.030(6) Uiso d 1
C C6 0.28439(19) 0.54868(18) 0.19161(16) 0.0200(3) Uani d 1
C C7 0.54289(18) 0.70675(18) 0.36558(16) 0.0192(3) Uani d 1
C C8 0.78540(18) 0.86088(18) 0.55745(15) 0.0191(3) Uani d 1
C C9 0.88618(18) 0.78022(18) 0.58540(16) 0.0190(3) Uani d 1
C C10 1.0487(2) 0.8571(2) 0.65130(18) 0.0246(3) Uani d 1
H H10 1.115(2) 0.803(2) 0.668(2) 0.023(5) Uiso d 1
C C11 1.1079(2) 1.0112(2) 0.68627(18) 0.0259(4) Uani d 1
H H11 1.216(3) 1.063(3) 0.728(2) 0.040(6) Uiso d 1
C C12 1.0078(2) 1.0906(2) 0.65271(17) 0.0241(3) Uani d 1
H H12 1.048(2) 1.191(2) 0.666(2) 0.025(5) Uiso d 1
C C13 0.8458(2) 1.01533(19) 0.58854(17) 0.0221(3) Uani d 1
H H13 0.776(2) 1.067(2) 0.564(2) 0.021(5) Uiso d 1
C C14 0.53423(19) 0.80575(18) 0.58434(16) 0.0193(3) Uani d 1
C C15 0.5869(2) 0.8912(2) 0.81793(17) 0.0239(3) Uani d 1
C C16 0.7421(3) 0.9359(3) 0.9349(2) 0.0343(4) Uani d 1
H H16A 0.734(3) 0.967(3) 1.013(3) 0.043(7) Uiso d 1
H H16C 0.813(3) 1.004(3) 0.926(2) 0.042(7) Uiso d 1
C C17 0.5305(3) 1.0216(3) 0.8070(2) 0.0378(5) Uani d 1
H H17A 0.608(3) 1.099(3) 0.801(2) 0.033(6) Uiso d 1
H H17B 0.436(3) 0.997(3) 0.726(3) 0.039(6) Uiso d 1
H H17C 0.514(4) 1.044(3) 0.883(3) 0.063(9) Uiso d 1
C C18 0.4628(3) 0.7560(3) 0.8179(2) 0.0353(4) Uani d 1
H H18A 0.447(3) 0.781(3) 0.896(3) 0.055(8) Uiso d 1
H H18B 0.361(3) 0.723(3) 0.744(3) 0.044(7) Uiso d 1
H H18C 0.501(3) 0.673(3) 0.814(3) 0.054(8) Uiso d 1
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'
Se Se -0.0929 2.2259 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 Se1 Se2 . . 102.63(5)
C9 Se2 Se1 2_666 . 101.30(5)
C14 O3 C15 . . 121.28(13)
C7 N1 C6 . . 125.87(15)
C7 N1 H1 . . 115.5(16)
C6 N1 H1 . . 117.5(16)
C14 N2 C7 . . 125.19(13)
C14 N2 C8 . . 117.10(13)
C7 N2 C8 . . 117.67(13)
C2 C1 C6 . . 119.88(16)
C2 C1 Se1 . . 116.87(13)
C6 C1 Se1 . . 122.99(12)
C3 C2 C1 . . 120.76(17)
C3 C2 H2 . . 122.7(13)
C1 C2 H2 . . 116.5(13)
C2 C3 C4 . . 119.73(17)
C2 C3 H3 . . 118.1(15)
C4 C3 H3 . . 122.0(15)
C3 C4 C5 . . 120.40(18)
C3 C4 H4 . . 120.8(15)
C5 C4 H4 . . 118.6(15)
C6 C5 C4 . . 120.28(17)
C6 C5 H5 . . 118.9(14)
C4 C5 H5 . . 120.8(14)
C5 C6 N1 . . 123.14(15)
C5 C6 C1 . . 118.94(16)
N1 C6 C1 . . 117.91(15)
O1 C7 N1 . . 125.85(16)
O1 C7 N2 . . 118.81(14)
N1 C7 N2 . . 115.33(14)
C9 C8 C13 . . 120.65(15)
C9 C8 N2 . . 122.21(14)
C13 C8 N2 . . 117.10(14)
C8 C9 C10 . . 118.97(15)
C8 C9 Se2 . 2_666 118.80(12)
C10 C9 Se2 . 2_666 122.12(13)
C11 C10 C9 . . 120.19(16)
C11 C10 H10 . . 121.4(13)
C9 C10 H10 . . 118.4(13)
C12 C11 C10 . . 120.59(16)
C12 C11 H11 . . 118.4(15)
C10 C11 H11 . . 120.9(15)
C11 C12 C13 . . 119.62(17)
C11 C12 H12 . . 120.8(13)
C13 C12 H12 . . 119.4(13)
C12 C13 C8 . . 119.86(16)
C12 C13 H13 . . 121.2(12)
C8 C13 H13 . . 118.9(12)
O2 C14 O3 . . 126.26(15)
O2 C14 N2 . . 124.34(15)
O3 C14 N2 . . 109.40(13)
O3 C15 C17 . . 108.43(15)
O3 C15 C18 . . 109.81(15)
C17 C15 C18 . . 113.42(18)
O3 C15 C16 . . 101.27(14)
C17 C15 C16 . . 111.86(17)
C18 C15 C16 . . 111.31(17)
C15 C16 H16A . . 113.0(16)
C15 C16 H16C . . 108.9(17)
H16A C16 H16C . . 110(2)
C15 C17 H17A . . 110.0(14)
C15 C17 H17B . . 112.9(14)
H17A C17 H17B . . 105(2)
C15 C17 H17C . . 101.4(19)
H17A C17 H17C . . 113(2)
H17B C17 H17C . . 115(2)
C15 C18 H18A . . 107.7(17)
C15 C18 H18B . . 113.9(15)
H18A C18 H18B . . 109(2)
C15 C18 H18C . . 109.5(17)
H18A C18 H18C . . 110(2)
H18B C18 H18C . . 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Se1 C1 . 1.9235(17)
Se1 Se2 . 2.3327(2)
Se2 C9 2_666 1.9219(16)
O1 C7 . 1.214(2)
O2 C14 . 1.2128(19)
O3 C14 . 1.323(2)
O3 C15 . 1.486(2)
N1 C7 . 1.356(2)
N1 C6 . 1.407(2)
N1 H1 . 0.81(2)
N2 C14 . 1.401(2)
N2 C7 . 1.423(2)
N2 C8 . 1.4465(19)
C1 C2 . 1.388(2)
C1 C6 . 1.410(2)
C2 C3 . 1.382(3)
C2 H2 . 0.95(2)
C3 C4 . 1.385(3)
C3 H3 . 0.92(2)
C4 C5 . 1.394(3)
C4 H4 . 0.87(2)
C5 C6 . 1.394(2)
C5 H5 . 0.91(2)
C8 C9 . 1.389(2)
C8 C13 . 1.390(2)
C9 C10 . 1.395(2)
C10 C11 . 1.384(3)
C10 H10 . 0.92(2)
C11 C12 . 1.384(3)
C11 H11 . 0.93(2)
C12 C13 . 1.388(2)
C12 H12 . 0.92(2)
C13 H13 . 0.94(2)
C15 C17 . 1.513(3)
C15 C18 . 1.518(3)
C15 C16 . 1.522(3)
C16 H16A . 0.91(3)
C16 H16C . 0.85(3)
C17 H17A . 0.93(2)
C17 H17B . 0.99(3)
C17 H17C . 0.92(3)
C18 H18A . 0.94(3)
C18 H18B . 0.98(3)
C18 H18C . 0.96(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 Se1 . 0.81(2) 2.69(2) 3.1417(14) 116.8(18) yes
N1 H1 Se2 . 0.81(2) 3.09(2) 3.5417(15) 117.9(18) yes
N1 H1 O2 . 0.81(2) 1.96(2) 2.6454(19) 142(2) yes
C5 H5 O1 . 0.91(2) 2.36(2) 2.888(2) 116.8(17) yes
C10 H10 Se1 2_666 0.92(2) 3.02(2) 3.4886(18) 112.9(15) yes
C13 H13 O2 2_676 0.94(2) 2.65(2) 3.569(2) 166.0(17) yes
C17 H17B O2 . 0.99(3) 2.46(2) 3.018(3) 115.1(17) yes
C18 H18B O2 . 0.98(3) 2.47(3) 2.982(3) 112.2(18) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . -1.0(3)
Se1 C1 C2 C3 . . 173.31(14)
C1 C2 C3 C4 . . 0.0(3)
C2 C3 C4 C5 . . 0.5(3)
C3 C4 C5 C6 . . -0.1(3)
C4 C5 C6 N1 . . -179.62(16)
C4 C5 C6 C1 . . -0.8(3)
C7 N1 C6 C5 . . -28.0(3)
C7 N1 C6 C1 . . 153.19(16)
C2 C1 C6 C5 . . 1.3(2)
Se1 C1 C6 C5 . . -172.56(13)
C2 C1 C6 N1 . . -179.79(15)
Se1 C1 C6 N1 . . 6.3(2)
C6 N1 C7 O1 . . 11.6(3)
C6 N1 C7 N2 . . -167.49(15)
C14 N2 C7 O1 . . -170.50(15)
C8 N2 C7 O1 . . 7.2(2)
C14 N2 C7 N1 . . 8.6(2)
C8 N2 C7 N1 . . -173.70(14)
C14 N2 C8 C9 . . 103.85(18)
C7 N2 C8 C9 . . -74.0(2)
C14 N2 C8 C13 . . -73.60(19)
C7 N2 C8 C13 . . 108.54(17)
C13 C8 C9 C10 . . 3.3(2)
N2 C8 C9 C10 . . -174.09(15)
C13 C8 C9 Se2 . 2_666 -173.12(12)
N2 C8 C9 Se2 . 2_666 9.5(2)
C8 C9 C10 C11 . . -0.9(3)
Se2 C9 C10 C11 2_666 . 175.31(14)
C9 C10 C11 C12 . . -2.1(3)
C10 C11 C12 C13 . . 2.9(3)
C11 C12 C13 C8 . . -0.6(3)
C9 C8 C13 C12 . . -2.5(3)
N2 C8 C13 C12 . . 174.96(15)
C15 O3 C14 O2 . . -6.4(3)
C15 O3 C14 N2 . . 173.61(13)
C7 N2 C14 O2 . . -18.5(3)
C8 N2 C14 O2 . . 163.79(16)
C7 N2 C14 O3 . . 161.44(14)
C8 N2 C14 O3 . . -16.2(2)
C14 O3 C15 C17 . . -61.3(2)
C14 O3 C15 C18 . . 63.1(2)
C14 O3 C15 C16 . . -179.11(16)

_cod_database_fobs_code 2021523
