#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:19:51 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179890 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/86/7018654.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_7018654
loop_
_publ_author_name
'Clegg, Jack K.'
'Harrowfield, Jack'
'Kim, Yang'
'Lee, Young Hoon'
'Lehn, Jean-Marie'
'Lim, Woo Taik'
'Thuéry, Pierre'
_publ_section_title
;
 Chelation-controlled molecular morphology: aminal to imine
 rearrangements.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              4335
_journal_page_last               4357
_journal_paper_doi               10.1039/c2dt12250b
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C23 H24 N6 O1, 3(H2 O)'
_chemical_formula_sum            'C23 H30 N6 O4'
_chemical_formula_weight         454.48
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2160(18)
_cell_length_b                   13.813(3)
_cell_length_c                   17.342(4)
_cell_measurement_reflns_used    9490
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.0
_cell_volume                     2207.6(8)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material
'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'ADSC Quantum210'
_diffrn_measurement_method       'two φ and two ω scans with 2° steps'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'synchrotron radiation'
_diffrn_radiation_type           'synchrotron radiation'
_diffrn_radiation_wavelength     0.76999
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9490
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.36
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.9(12)
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1392P)²+0.4397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                5010
_reflns_number_total             5181
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt12250b.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'NONE' changed to 'none'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               7018654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.5337(2) 0.49545(13) 0.34976(10) 0.0204(3) Uani 1 1 d .
H1 H 0.5222 0.4325 0.3752 0.024 Uiso 1 1 calc R
C2 C 0.40134(19) 0.61312(12) 0.27564(10) 0.0186(3) Uani 1 1 d .
H2 H 0.4518 0.6613 0.3073 0.022 Uiso 1 1 calc R
C3 C 0.6376(2) 0.56974(12) 0.23821(10) 0.0186(3) Uani 1 1 d .
H3 H 0.6663 0.6217 0.2736 0.022 Uiso 1 1 calc R
C4 C 0.4231(2) 0.42370(12) 0.20773(10) 0.0203(3) Uani 1 1 d .
C5 C 0.5762(2) 0.39976(13) 0.23747(11) 0.0218(4) Uani 1 1 d .
H5A H 0.5726 0.3411 0.2682 0.026 Uiso 1 1 calc R
H5B H 0.6402 0.3882 0.1940 0.026 Uiso 1 1 calc R
C6 C 0.4347(2) 0.51725(12) 0.16013(10) 0.0193(3) Uani 1 1 d .
H6A H 0.4975 0.5064 0.1161 0.023 Uiso 1 1 calc R
H6B H 0.3394 0.5351 0.1410 0.023 Uiso 1 1 calc R
C7 C 0.3258(2) 0.44555(13) 0.27768(11) 0.0215(4) Uani 1 1 d .
H7A H 0.2295 0.4629 0.2599 0.026 Uiso 1 1 calc R
H7B H 0.3173 0.3879 0.3093 0.026 Uiso 1 1 calc R
C8 C 0.2551(2) 0.65809(13) 0.25478(10) 0.0226(4) Uani 1 1 d .
C9 C 0.1404(2) 0.65681(17) 0.30663(13) 0.0298(4) Uani 1 1 d .
H9 H 0.1465 0.6211 0.3520 0.036 Uiso 1 1 calc R
C10 C 0.0156(2) 0.71006(18) 0.28963(15) 0.0375(5) Uani 1 1 d .
H10 H -0.0620 0.7115 0.3239 0.045 Uiso 1 1 calc R
C11 C 0.0099(3) 0.76055(18) 0.22104(16) 0.0389(5) Uani 1 1 d .
H11 H -0.0716 0.7969 0.2082 0.047 Uiso 1 1 calc R
C12 C 0.1269(3) 0.75606(16) 0.17217(14) 0.0345(5) Uani 1 1 d .
H12 H 0.1211 0.7890 0.1255 0.041 Uiso 1 1 calc R
C13 C 0.7534(2) 0.56609(14) 0.17607(10) 0.0225(4) Uani 1 1 d .
C14 C 0.8773(2) 0.51109(16) 0.18575(13) 0.0297(4) Uani 1 1 d .
H14 H 0.8877 0.4712 0.2286 0.036 Uiso 1 1 calc R
C15 C 0.9859(2) 0.5163(2) 0.13059(15) 0.0391(5) Uani 1 1 d .
H15 H 1.0706 0.4804 0.1360 0.047 Uiso 1 1 calc R
C16 C 0.9663(3) 0.5757(2) 0.06751(13) 0.0399(6) Uani 1 1 d .
H16 H 1.0382 0.5815 0.0301 0.048 Uiso 1 1 calc R
C17 C 0.8382(3) 0.6263(2) 0.06110(13) 0.0384(5) Uani 1 1 d .
H17 H 0.8240 0.6645 0.0176 0.046 Uiso 1 1 calc R
C18 C 0.6019(2) 0.56263(13) 0.40914(10) 0.0209(4) Uani 1 1 d .
C19 C 0.7506(2) 0.55687(15) 0.42316(11) 0.0261(4) Uani 1 1 d .
H19 H 0.8088 0.5159 0.3939 0.031 Uiso 1 1 calc R
C20 C 0.8108(2) 0.61316(16) 0.48137(13) 0.0302(4) Uani 1 1 d .
H20 H 0.9097 0.6104 0.4918 0.036 Uiso 1 1 calc R
C21 C 0.7208(3) 0.67343(16) 0.52350(12) 0.0295(4) Uani 1 1 d .
H21 H 0.7579 0.7126 0.5624 0.035 Uiso 1 1 calc R
C22 C 0.5735(2) 0.67404(15) 0.50628(11) 0.0275(4) Uani 1 1 d .
H22 H 0.5132 0.7140 0.5352 0.033 Uiso 1 1 calc R
C23 C 0.3692(2) 0.33761(13) 0.16089(12) 0.0252(4) Uani 1 1 d .
H23A H 0.4400 0.3231 0.1211 0.030 Uiso 1 1 calc R
H23B H 0.3630 0.2817 0.1945 0.030 Uiso 1 1 calc R
N1 N 0.63439(17) 0.47977(11) 0.28468(9) 0.0196(3) Uani 1 1 d .
N2 N 0.38577(17) 0.52580(11) 0.32488(9) 0.0194(3) Uani 1 1 d .
N3 N 0.49392(16) 0.59698(11) 0.20800(8) 0.0183(3) Uani 1 1 d .
N4 N 0.2494(2) 0.70682(12) 0.18772(10) 0.0268(4) Uani 1 1 d .
N5 N 0.7324(2) 0.62350(14) 0.11451(10) 0.0292(4) Uani 1 1 d .
N6 N 0.51350(19) 0.62012(12) 0.45013(9) 0.0239(3) Uani 1 1 d .
O1 O 0.23238(17) 0.35211(11) 0.12553(9) 0.0294(3) Uani 1 1 d .
H1A H 0.2433 0.3813 0.0848 0.044 Uiso 1 1 calc R
O2 O 0.71458(19) 0.93474(14) 0.51398(9) 0.0391(4) Uani 1 1 d .
O3 O 0.4796(3) 0.73453(13) 0.07530(10) 0.0468(5) Uani 1 1 d .
O4 O 0.893(3) 0.8869(15) 0.0426(6) 0.058(4) Uani 0.33(4) 1 d P
O4' O 0.822(3) 0.8665(6) 0.0401(3) 0.070(4) Uani 0.67(4) 1 d P
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
N1 C1 N2 113.25(13)
N1 C1 C18 110.29(15)
N2 C1 C18 113.73(15)
N3 C2 N2 113.11(13)
N3 C2 C8 112.67(14)
N2 C2 C8 112.42(15)
N3 C3 N1 112.95(14)
N3 C3 C13 112.84(14)
N1 C3 C13 111.86(14)
C23 C4 C6 113.10(15)
C23 C4 C5 108.07(15)
C6 C4 C5 107.30(14)
C23 C4 C7 112.54(15)
C6 C4 C7 107.40(14)
C5 C4 C7 108.21(15)
N1 C5 C4 111.00(14)
N3 C6 C4 110.43(13)
N2 C7 C4 111.35(14)
N4 C8 C9 122.47(18)
N4 C8 C2 116.28(17)
C9 C8 C2 120.90(17)
C8 C9 C10 118.9(2)
C11 C10 C9 118.7(2)
C12 C11 C10 118.6(2)
N4 C12 C11 123.9(2)
N5 C13 C14 122.69(19)
N5 C13 C3 116.30(17)
C14 C13 C3 120.88(17)
C13 C14 C15 119.0(2)
C16 C15 C14 118.9(2)
C17 C16 C15 118.6(2)
N5 C17 C16 123.5(2)
N6 C18 C19 122.59(18)
N6 C18 C1 117.92(16)
C19 C18 C1 119.30(17)
C20 C19 C18 119.2(2)
C21 C20 C19 118.7(2)
C20 C21 C22 118.41(19)
N6 C22 C21 123.65(19)
O1 C23 C4 114.26(16)
C5 N1 C1 107.77(14)
C5 N1 C3 109.48(14)
C1 N1 C3 107.77(13)
C7 N2 C2 108.99(13)
C7 N2 C1 106.87(14)
C2 N2 C1 107.86(13)
C2 N3 C3 106.09(13)
C2 N3 C6 110.25(14)
C3 N3 C6 109.90(13)
C8 N4 C12 117.3(2)
C13 N5 C17 117.4(2)
C18 N6 C22 117.47(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.477(2)
C1 N2 1.490(2)
C1 C18 1.522(2)
C2 N3 1.468(2)
C2 N2 1.485(2)
C2 C8 1.527(3)
C3 N3 1.473(2)
C3 N1 1.482(2)
C3 C13 1.517(2)
C4 C23 1.524(2)
C4 C6 1.537(2)
C4 C5 1.538(3)
C4 C7 1.538(3)
C5 N1 1.476(2)
C6 N3 1.483(2)
C7 N2 1.485(2)
C8 N4 1.345(3)
C8 C9 1.388(3)
C9 C10 1.396(3)
C10 C11 1.380(4)
C11 C12 1.373(4)
C12 N4 1.346(3)
C13 N5 1.344(3)
C13 C14 1.382(3)
C14 C15 1.387(3)
C15 C16 1.379(4)
C16 C17 1.377(4)
C17 N5 1.346(3)
C18 N6 1.342(2)
C18 C19 1.394(3)
C19 C20 1.390(3)
C20 C21 1.384(3)
C21 C22 1.389(3)
C22 N6 1.345(3)
C23 O1 1.416(2)
O4 O4' 0.721(10)
