#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:06:25 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180123 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/21/7102133.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_7102133
loop_
_publ_author_name
'Li, Sze-Wan'
'Batey, Robert A'
_publ_section_title
;
 Mild lanthanide(III) catalyzed formation of
 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines:
 a domino condensation/ring-opening/electrocyclization process.
;
_journal_issue                   36
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3759
_journal_page_last               3761
_journal_paper_doi               10.1039/b709337n
_journal_year                    2007
_chemical_formula_moiety         'C37 H40 N2 O5'
_chemical_formula_sum            'C37 H40 N2 O5'
_chemical_formula_weight         592.71
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 94.869(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3806(4)
_cell_length_b                   23.213(1)
_cell_length_c                   13.4673(6)
_cell_measurement_reflns_used    5707
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.6
_cell_volume                     3233.4(2)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'SHELXTL V6.12'
_computing_publication_material  'SHELXTL V6.12'
_computing_structure_refinement  'SHELXTL V6.12(Sheldrick, 2001)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.097
_diffrn_reflns_av_sigmaI/netI    0.092
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22437
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.59
_diffrn_standards_decay_%        9
_diffrn_standards_number         9
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Denzo-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0071(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     410
_refine_ls_number_reflns         5707
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1210
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0769P)²+0.4544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1773
_reflns_number_gt                3338
_reflns_number_total             5707
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b709337n.txt
_cod_data_source_block           k01288
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7102133
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
_atom_site_disorder_group
O1 O 0.5606(2) 0.29479(10) 0.59518(15) 0.0635(6) Uani 1 1 d . .
O2 O 0.3945(3) 0.04396(13) 0.1185(2) 0.0996(9) Uani 1 1 d D .
O3 O 0.9214(2) 0.39114(10) 0.11204(15) 0.0628(6) Uani 1 1 d . .
O4 O 0.9160(2) 0.01303(9) 0.22886(16) 0.0694(7) Uani 1 1 d . .
O5 O 1.33619(19) 0.41620(10) 0.31016(17) 0.0668(6) Uani 1 1 d . .
N1 N 0.64794(19) 0.23049(10) 0.41569(15) 0.0412(6) Uani 1 1 d . .
N2 N 0.96632(19) 0.23824(10) 0.49980(15) 0.0412(6) Uani 1 1 d . .
C1 C 0.6611(3) 0.26791(13) 0.5927(2) 0.0463(7) Uani 1 1 d . .
C2 C 0.7292(2) 0.25604(12) 0.49859(18) 0.0409(7) Uani 1 1 d . .
H2A H 0.7642 0.2933 0.4752 0.049 Uiso 1 1 calc R .
C3 C 0.8442(2) 0.21721(12) 0.53390(19) 0.0402(7) Uani 1 1 d . .
H3A H 0.8273 0.1781 0.5044 0.048 Uiso 1 1 calc R .
C4 C 0.8369(3) 0.21232(14) 0.6450(2) 0.0483(7) Uani 1 1 d . .
H4A H 0.898(3) 0.1867(12) 0.695(2) 0.058 Uiso 1 1 d . .
C5 C 0.7348(3) 0.23983(14) 0.6759(2) 0.0537(8) Uani 1 1 d . .
H5A H 0.7132 0.2409 0.7430 0.064 Uiso 1 1 calc R .
C6 C 0.5601(3) 0.18563(13) 0.4469(2) 0.0470(7) Uani 1 1 d . .
H6A H 0.4838 0.2040 0.4732 0.056 Uiso 1 1 calc R .
H6B H 0.6048 0.1624 0.5011 0.056 Uiso 1 1 calc R .
C7 C 0.5160(3) 0.14670(13) 0.3611(2) 0.0452(7) Uani 1 1 d . .
C8 C 0.6042(3) 0.11912(14) 0.3068(2) 0.0534(8) Uani 1 1 d . .
H8A H 0.6940 0.1239 0.3252 0.064 Uiso 1 1 calc R .
C9 C 0.5652(3) 0.08456(14) 0.2261(2) 0.0613(9) Uani 1 1 d . .
H9A H 0.6275 0.0659 0.1895 0.074 Uiso 1 1 calc R .
C10 C 0.4343(3) 0.07745(15) 0.1991(2) 0.0630(9) Uani 1 1 d . .
C11 C 0.3450(3) 0.10385(15) 0.2530(3) 0.0662(10) Uani 1 1 d . .
H11A H 0.2552 0.0986 0.2353 0.079 Uiso 1 1 calc R .
C12 C 0.3864(3) 0.13807(15) 0.3333(2) 0.0579(8) Uani 1 1 d . .
H12A H 0.3239 0.1562 0.3705 0.069 Uiso 1 1 calc R .
C13* C 0.4768(8) 0.0140(3) 0.0580(6) 0.109(3) Uani 0.50 1 d PD 1
H13A H 0.4246 -0.0070 0.0059 0.163 Uiso 0.50 1 calc PR 1
H13B H 0.5302 -0.0132 0.0990 0.163 Uiso 0.50 1 calc PR 1
H13C H 0.5328 0.0416 0.0271 0.163 Uiso 0.50 1 calc PR 1
C13 C 0.2690(5) 0.0483(4) 0.0697(6) 0.111(3) Uani 0.50 1 d PD 2
H13D H 0.2597 0.0208 0.0144 0.166 Uiso 0.50 1 calc PR 2
H13E H 0.2552 0.0875 0.0438 0.166 Uiso 0.50 1 calc PR 2
H13F H 0.2049 0.0398 0.1170 0.166 Uiso 0.50 1 calc PR 2
C14 C 0.5801(2) 0.27306(13) 0.3499(2) 0.0453(7) Uani 1 1 d . .
H14A H 0.5332 0.3003 0.3904 0.054 Uiso 1 1 calc R .
H14B H 0.5156 0.2531 0.3035 0.054 Uiso 1 1 calc R .
C15 C 0.6726(2) 0.30626(12) 0.29046(19) 0.0406(7) Uani 1 1 d . .
C16 C 0.6586(3) 0.36505(13) 0.2743(2) 0.0473(7) Uani 1 1 d . .
H16A H 0.5921 0.3851 0.3041 0.057 Uiso 1 1 calc R .
C17 C 0.7395(3) 0.39538(14) 0.2155(2) 0.0501(8) Uani 1 1 d . .
H17A H 0.7288 0.4357 0.2060 0.060 Uiso 1 1 calc R .
C18 C 0.8353(3) 0.36611(14) 0.1713(2) 0.0475(7) Uani 1 1 d . .
C19 C 0.8520(3) 0.30767(13) 0.1874(2) 0.0455(7) Uani 1 1 d . .
H19A H 0.9191 0.2877 0.1580 0.055 Uiso 1 1 calc R .
C20 C 0.7716(2) 0.27821(13) 0.24628(18) 0.0421(7) Uani 1 1 d . .
H20A H 0.7840 0.2381 0.2568 0.051 Uiso 1 1 calc R .
C21 C 0.8988(4) 0.44925(17) 0.0831(3) 0.0954(13) Uani 1 1 d . .
H21A H 0.9664 0.4620 0.0416 0.143 Uiso 1 1 calc R .
H21B H 0.9000 0.4736 0.1427 0.143 Uiso 1 1 calc R .
H21C H 0.8142 0.4524 0.0452 0.143 Uiso 1 1 calc R .
C22 C 1.0651(2) 0.19266(12) 0.4997(2) 0.0469(7) Uani 1 1 d . .
H22A H 1.0790 0.1758 0.5672 0.056 Uiso 1 1 calc R .
H22B H 1.1478 0.2097 0.4827 0.056 Uiso 1 1 calc R .
C23 C 1.0258(2) 0.14595(12) 0.4263(2) 0.0437(7) Uani 1 1 d . .
C24 C 0.9979(3) 0.09066(14) 0.4576(2) 0.0584(8) Uani 1 1 d . .
H24A H 1.0047 0.0823 0.5269 0.070 Uiso 1 1 calc R .
C25 C 0.9607(3) 0.04756(14) 0.3904(2) 0.0636(9) Uani 1 1 d . .
H25A H 0.9417 0.0101 0.4137 0.076 Uiso 1 1 calc R .
C26 C 0.9511(3) 0.05893(13) 0.2896(2) 0.0503(8) Uani 1 1 d . .
C27 C 0.9749(3) 0.11387(13) 0.2558(2) 0.0477(7) Uani 1 1 d . .
H27A H 0.9662 0.1224 0.1866 0.057 Uiso 1 1 calc R .
C28 C 1.0117(3) 0.15634(13) 0.3251(2) 0.0457(7) Uani 1 1 d . .
H28A H 1.0279 0.1941 0.3018 0.055 Uiso 1 1 calc R .
C29 C 0.9187(5) 0.02058(17) 0.1244(3) 0.1010(15) Uani 1 1 d . .
H29A H 0.8924 -0.0153 0.0902 0.152 Uiso 1 1 calc R .
H29B H 1.0065 0.0307 0.1092 0.152 Uiso 1 1 calc R .
H29C H 0.8590 0.0515 0.1018 0.152 Uiso 1 1 calc R .
C30 C 1.0180(3) 0.28976(13) 0.5538(2) 0.0459(7) Uani 1 1 d . .
H30A H 1.0692 0.2778 0.6157 0.055 Uiso 1 1 calc R .
H30B H 0.9454 0.3140 0.5725 0.055 Uiso 1 1 calc R .
C31 C 1.1017(3) 0.32401(12) 0.4900(2) 0.0445(7) Uani 1 1 d . .
C32 C 1.0484(3) 0.34896(13) 0.4024(2) 0.0515(8) Uani 1 1 d . .
H32A H 0.9585 0.3445 0.3845 0.062 Uiso 1 1 calc R .
C33 C 1.1223(3) 0.38019(14) 0.3403(2) 0.0549(8) Uani 1 1 d . .
H33A H 1.0835 0.3969 0.2806 0.066 Uiso 1 1 calc R .
C34 C 1.2536(3) 0.38676(13) 0.3664(2) 0.0527(8) Uani 1 1 d . .
C35 C 1.3086(3) 0.36259(14) 0.4533(2) 0.0545(8) Uani 1 1 d . .
H35A H 1.3985 0.3672 0.4714 0.065 Uiso 1 1 calc R .
C36 C 1.2332(3) 0.33168(13) 0.5144(2) 0.0497(8) Uani 1 1 d . .
H36A H 1.2722 0.3154 0.5743 0.060 Uiso 1 1 calc R .
C37 C 1.2825(3) 0.44141(16) 0.2196(3) 0.0749(10) Uani 1 1 d . .
H37A H 1.3508 0.4611 0.1867 0.112 Uiso 1 1 calc R .
H37B H 1.2157 0.4693 0.2341 0.112 Uiso 1 1 calc R .
H37C H 1.2440 0.4112 0.1757 0.112 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 0.0033 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_3
C10 O2 C13* 125.4(5) .
C10 O2 C13 122.1(4) .
C13* O2 C13 110.3(6) .
C18 O3 C21 117.4(3) .
C26 O4 C29 117.9(3) .
C34 O5 C37 117.4(2) .
C2 N1 C14 113.8(2) .
C2 N1 C6 113.6(2) .
C14 N1 C6 111.9(2) .
C3 N2 C22 112.4(2) .
C3 N2 C30 113.7(2) .
C22 N2 C30 111.0(2) .
O1 C1 C5 127.1(3) .
O1 C1 C2 125.0(3) .
C5 C1 C2 107.9(2) .
N1 C2 C1 115.3(2) .
N1 C2 C3 112.3(2) .
C1 C2 C3 104.5(2) .
N2 C3 C4 116.9(2) .
N2 C3 C2 112.1(2) .
C4 C3 C2 104.4(2) .
C5 C4 C3 112.4(3) .
C4 C5 C1 110.7(3) .
N1 C6 C7 111.2(2) .
C8 C7 C12 117.8(3) .
C8 C7 C6 120.9(2) .
C12 C7 C6 121.3(3) .
C7 C8 C9 121.5(3) .
C8 C9 C10 119.3(3) .
C11 C10 O2 120.1(3) .
C11 C10 C9 120.0(3) .
O2 C10 C9 119.9(3) .
C10 C11 C12 119.6(3) .
C7 C12 C11 121.8(3) .
O2 C13* C13* 154.2(10) 3_655
N1 C14 C15 111.7(2) .
C16 C15 C20 117.7(3) .
C16 C15 C14 121.4(2) .
C20 C15 C14 120.8(3) .
C15 C16 C17 121.7(3) .
C18 C17 C16 119.2(3) .
O3 C18 C17 124.7(3) .
O3 C18 C19 115.2(3) .
C17 C18 C19 120.1(3) .
C20 C19 C18 120.1(3) .
C19 C20 C15 121.2(3) .
N2 C22 C23 111.7(2) .
C28 C23 C24 117.0(3) .
C28 C23 C22 121.6(3) .
C24 C23 C22 121.3(3) .
C25 C24 C23 121.6(3) .
C26 C25 C24 119.9(3) .
O4 C26 C25 115.6(3) .
O4 C26 C27 124.4(3) .
C25 C26 C27 120.0(3) .
C26 C27 C28 118.7(3) .
C23 C28 C27 122.7(3) .
N2 C30 C31 110.6(2) .
C32 C31 C36 117.5(3) .
C32 C31 C30 119.9(2) .
C36 C31 C30 122.6(3) .
C31 C32 C33 122.0(3) .
C34 C33 C32 119.1(3) .
O5 C34 C35 116.0(3) .
O5 C34 C33 124.1(3) .
C35 C34 C33 119.9(3) .
C34 C35 C36 120.1(3) .
C35 C36 C31 121.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.219(3) .
O2 C10 1.370(4) .
O2 C13* 1.412(2) .
O2 C13 1.413(2) .
O3 C18 1.376(3) .
O3 C21 1.418(4) .
O4 C26 1.373(3) .
O4 C29 1.420(4) .
O5 C34 1.373(3) .
O5 C37 1.423(4) .
N1 C2 1.466(3) .
N1 C14 1.467(3) .
N1 C6 1.469(3) .
N2 C3 1.468(3) .
N2 C22 1.473(3) .
N2 C30 1.476(3) .
C1 C5 1.457(4) .
C1 C2 1.527(4) .
C2 C3 1.538(4) .
C3 C4 1.509(4) .
C4 C5 1.334(4) .
C6 C7 1.507(4) .
C7 C8 1.377(4) .
C7 C12 1.380(4) .
C8 C9 1.384(4) .
C9 C10 1.386(4) .
C10 C11 1.370(5) .
C11 C12 1.380(4) .
C13* C13* 1.796(11) 3_655
C14 C15 1.512(4) .
C15 C16 1.388(4) .
C15 C20 1.392(4) .
C16 C17 1.393(4) .
C17 C18 1.381(4) .
C18 C19 1.382(4) .
C19 C20 1.380(4) .
C22 C23 1.500(4) .
C23 C28 1.380(4) .
C23 C24 1.389(4) .
C24 C25 1.382(4) .
C25 C26 1.379(4) .
C26 C27 1.383(4) .
C27 C28 1.388(4) .
C30 C31 1.501(4) .
C31 C32 1.386(4) .
C31 C36 1.388(4) .
C32 C33 1.387(4) .
C33 C34 1.386(4) .
C34 C35 1.378(4) .
C35 C36 1.383(4) .
