#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/23/1512366.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_1512366
loop_
_publ_author_name
'Cordes, Jens'
'Murray, Philip R. D.'
'White, Andrew J. P.'
'Barrett, Anthony G. M.'
_publ_section_title
;
 1,7-Diazaspiro[5.5]undecane - A Neglected Heterocycle.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4992
_journal_page_last               4995
_journal_paper_doi               10.1021/ol402301g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C46 H56 Cu2 N4 O8, 0.17(C6 H14)'
_chemical_formula_sum            'C47 H58.33 Cu2 N4 O8'
_chemical_formula_weight         934.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           147
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3'
_symmetry_space_group_name_H-M   'P -3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            3
_cell_length_a                   18.68118(13)
_cell_length_b                   18.68118(13)
_cell_length_c                   11.51988(9)
_cell_measurement_reflns_used    10911
_cell_measurement_temperature    173
_cell_measurement_theta_max      72.1530
_cell_measurement_theta_min      2.7080
_cell_volume                     3481.67(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21755
_diffrn_reflns_theta_full        72.44
_diffrn_reflns_theta_max         72.44
_diffrn_reflns_theta_min         2.73
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.579
_exptl_absorpt_correction_T_max  0.807
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   analytical
_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) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            Blue
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1471
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_platon_squeeze_details
;
SQUEEZE suggested 51 e/cell = 8.5 e/asu
The solvents used were methanol (CH4O, 18e), dcm (CH2Cl2, 42e) and
n-hexane (C6H14, 50e).
Before the use of SQUEEZE the solvent (positioned across a -3 site) most
resembled hexane
1/6hexane = 8.3e, so this was used as the solvent present.
 
So, the atom list is low by 1/6(C6 H14) = C H2.33, and the UNIT
is low by C3 H7, i.e. C138 H168 N12 O24 Cu6
;
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4559
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0554P)²+1.4193P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                3911
_reflns_number_total             4559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol402301g_si_001.cif
_cod_data_source_block           31
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        3481.67(6)
_cod_original_sg_symbol_H-M      P-3
_cod_database_code               1512366
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.486483(17) 0.017271(16) 0.26662(2) 0.02601(11) Uani 1 1 d .
N1 N 0.58290(10) 0.11201(10) 0.18659(14) 0.0276(3) Uani 1 1 d .
C2 C 0.58569(14) 0.09668(14) 0.06103(18) 0.0370(5) Uani 1 1 d .
H2A H 0.5299 0.0764 0.0280 0.044 Uiso 1 1 calc R
H2B H 0.5994 0.0522 0.0516 0.044 Uiso 1 1 calc R
C3 C 0.64700(16) 0.17104(16) -0.0081(2) 0.0466(6) Uani 1 1 d .
H3A H 0.6550 0.1531 -0.0855 0.056 Uiso 1 1 calc R
H3B H 0.6253 0.2093 -0.0194 0.056 Uiso 1 1 calc R
C4 C 0.72777(16) 0.21457(17) 0.0546(2) 0.0473(6) Uani 1 1 d .
H4A H 0.7678 0.2632 0.0091 0.057 Uiso 1 1 calc R
H4B H 0.7504 0.1770 0.0635 0.057 Uiso 1 1 calc R
C5 C 0.71538(13) 0.24228(13) 0.17401(18) 0.0328(4) Uani 1 1 d .
H5A H 0.7648 0.2574 0.2223 0.039 Uiso 1 1 calc R
H5B H 0.7103 0.2923 0.1648 0.039 Uiso 1 1 calc R
C6 C 0.63957(12) 0.17651(12) 0.23651(17) 0.0264(4) Uani 1 1 d .
C7 C 0.63120(12) 0.19131(12) 0.36284(17) 0.0275(4) Uani 1 1 d .
H7A H 0.5782 0.1453 0.3919 0.033 Uiso 1 1 calc R
H7B H 0.6285 0.2427 0.3699 0.033 Uiso 1 1 calc R
C8 C 0.70129(12) 0.19880(12) 0.44066(17) 0.0280(4) Uani 1 1 d .
H8A H 0.7020 0.1462 0.4380 0.034 Uiso 1 1 calc R
H8B H 0.7548 0.2428 0.4097 0.034 Uiso 1 1 calc R
C9 C 0.69274(12) 0.21871(12) 0.56712(17) 0.0287(4) Uani 1 1 d .
H9A H 0.7408 0.2245 0.6112 0.034 Uiso 1 1 calc R
H9B H 0.6952 0.2729 0.5693 0.034 Uiso 1 1 calc R
C10 C 0.61390(12) 0.15520(12) 0.62888(17) 0.0281(4) Uani 1 1 d .
H10A H 0.6123 0.1764 0.7070 0.034 Uiso 1 1 calc R
H10B H 0.5655 0.1488 0.5849 0.034 Uiso 1 1 calc R
N11 N 0.60695(10) 0.07329(10) 0.64131(15) 0.0285(4) Uani 1 1 d D
H11A H 0.6023(15) 0.0532(15) 0.5690(9) 0.037(7) Uiso 1 1 d D
H11B H 0.6526(8) 0.0787(14) 0.6758(18) 0.030(6) Uiso 1 1 d D
O20 O 0.37604(10) 0.00552(10) 0.12414(14) 0.0388(4) Uani 1 1 d .
C20 C 0.37876(12) 0.05634(12) 0.19590(18) 0.0290(4) Uani 1 1 d .
O21 O 0.42756(9) 0.08081(8) 0.28325(13) 0.0310(3) Uani 1 1 d .
C22 C 0.32178(12) 0.09103(12) 0.18394(17) 0.0284(4) Uani 1 1 d .
C23 C 0.27318(15) 0.07429(14) 0.0854(2) 0.0376(5) Uani 1 1 d .
H23A H 0.2755 0.0404 0.0257 0.045 Uiso 1 1 calc R
C24 C 0.22124(17) 0.10709(17) 0.0743(2) 0.0479(6) Uani 1 1 d .
H24A H 0.1881 0.0957 0.0068 0.057 Uiso 1 1 calc R
C25 C 0.21759(18) 0.15607(18) 0.1608(2) 0.0506(6) Uani 1 1 d .
H25A H 0.1821 0.1785 0.1528 0.061 Uiso 1 1 calc R
C26 C 0.26546(17) 0.17263(16) 0.2592(2) 0.0450(6) Uani 1 1 d .
H26A H 0.2628 0.2063 0.3189 0.054 Uiso 1 1 calc R
C27 C 0.31739(14) 0.14024(13) 0.2711(2) 0.0339(5) Uani 1 1 d .
H27A H 0.3502 0.1516 0.3390 0.041 Uiso 1 1 calc R
O30 O 0.58709(10) -0.00241(9) 0.40989(14) 0.0372(3) Uani 1 1 d .
C30 C 0.58193(12) -0.04376(12) 0.32283(18) 0.0292(4) Uani 1 1 d .
O31 O 0.53818(9) -0.05038(8) 0.23414(12) 0.0309(3) Uani 1 1 d .
C32 C 0.62802(12) -0.09099(11) 0.31877(18) 0.0291(4) Uani 1 1 d .
C33 C 0.67119(14) -0.09214(14) 0.4160(2) 0.0368(5) Uani 1 1 d .
H33A H 0.6708 -0.0642 0.4847 0.044 Uiso 1 1 calc R
C34 C 0.71513(16) -0.13423(16) 0.4128(2) 0.0456(6) Uani 1 1 d .
H34A H 0.7453 -0.1345 0.4790 0.055 Uiso 1 1 calc R
C35 C 0.71477(16) -0.17576(16) 0.3128(2) 0.0466(6) Uani 1 1 d .
H35A H 0.7447 -0.2046 0.3107 0.056 Uiso 1 1 calc R
C36 C 0.67126(16) -0.17543(15) 0.2165(2) 0.0430(5) Uani 1 1 d .
H36A H 0.6708 -0.2043 0.1484 0.052 Uiso 1 1 calc R
C37 C 0.62801(14) -0.13282(13) 0.2189(2) 0.0352(5) Uani 1 1 d .
H37A H 0.5984 -0.1323 0.1522 0.042 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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_3
O31 Cu1 O21 173.75(6) .
O31 Cu1 N1 88.10(6) .
O21 Cu1 N1 92.20(6) .
O31 Cu1 N11 93.31(6) 4_656
O21 Cu1 N11 86.85(6) 4_656
N1 Cu1 N11 175.60(7) 4_656
C6 N1 C2 122.02(17) .
C6 N1 Cu1 125.45(14) .
C2 N1 Cu1 112.37(13) .
N1 C2 C3 114.89(18) .
C4 C3 C2 109.9(2) .
C3 C4 C5 109.7(2) .
C6 C5 C4 113.07(18) .
N1 C6 C7 119.76(18) .
N1 C6 C5 123.35(18) .
C7 C6 C5 116.86(17) .
C6 C7 C8 114.82(16) .
C9 C8 C7 112.95(16) .
C10 C9 C8 115.56(16) .
N11 C10 C9 113.63(16) .
C10 N11 Cu1 120.68(13) 4_656
O20 C20 O21 123.14(19) .
O20 C20 C22 120.12(19) .
O21 C20 C22 116.73(17) .
C20 O21 Cu1 102.65(12) .
C23 C22 C27 119.40(19) .
C23 C22 C20 120.14(18) .
C27 C22 C20 120.46(19) .
C22 C23 C24 119.9(2) .
C25 C24 C23 120.3(2) .
C24 C25 C26 120.1(2) .
C25 C26 C27 120.1(2) .
C26 C27 C22 120.3(2) .
O30 C30 O31 123.70(19) .
O30 C30 C32 119.97(19) .
O31 C30 C32 116.33(17) .
C30 O31 Cu1 106.34(12) .
C33 C32 C37 119.74(19) .
C33 C32 C30 119.33(19) .
C37 C32 C30 120.93(19) .
C32 C33 C34 119.9(2) .
C35 C34 C33 119.9(2) .
C36 C35 C34 120.3(2) .
C35 C36 C37 120.0(2) .
C36 C37 C32 120.1(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O31 1.9723(14) .
Cu1 O21 1.9910(14) .
Cu1 N1 2.0097(17) .
Cu1 N11 2.0201(17) 4_656
N1 C6 1.276(3) .
N1 C2 1.480(3) .
C2 C3 1.512(3) .
C3 C4 1.494(4) .
C4 C5 1.528(3) .
C5 C6 1.514(3) .
C6 C7 1.504(3) .
C7 C8 1.534(3) .
C8 C9 1.532(3) .
C9 C10 1.528(3) .
C10 N11 1.477(2) .
N11 Cu1 2.0201(17) 4_656
O20 C20 1.241(3) .
C20 O21 1.279(3) .
C20 C22 1.504(3) .
C22 C23 1.388(3) .
C22 C27 1.391(3) .
C23 C24 1.388(3) .
C24 C25 1.378(4) .
C25 C26 1.380(4) .
C26 C27 1.383(3) .
O30 C30 1.240(3) .
C30 O31 1.275(3) .
C30 C32 1.510(3) .
C32 C33 1.387(3) .
C32 C37 1.391(3) .
C33 C34 1.392(3) .
C34 C35 1.387(4) .
C35 C36 1.377(4) .
C36 C37 1.389(3) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 -0.022 276 49 ' '
2 0.333 0.667 0.193 43 1 ' '
3 0.667 0.333 0.807 43 1 ' '
