#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:44:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178791 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/45/4104514.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_4104514
loop_
_publ_author_name
'David J. Hardee'
'Tristan H. Lambert'
_publ_section_title
;
 Lanthanum(III) Triflate-Catalyzed Cyclopropanation via Intramolecular
 Methylene Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7536
_journal_page_last               7537
_journal_paper_doi               10.1021/ja902137z
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C22 H26 N4 O5'
_chemical_formula_weight         426.47
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.527(2)
_cell_angle_beta                 94.330(2)
_cell_angle_gamma                95.501(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0477(9)
_cell_length_b                   9.0172(12)
_cell_length_c                   17.499(2)
_cell_measurement_reflns_used    4908
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      2.36
_cell_volume                     1070.7(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      125(2)
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18656
_diffrn_reflns_theta_full        32.49
_diffrn_reflns_theta_max         32.49
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.9821
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         7308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0520
_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)+(0.0541P)²+0.0139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1306
_reflns_number_gt                4240
_reflns_number_total             7308
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja902137z_si_002.cif
_cod_data_source_block           dhcps10
_cod_database_code               4104514
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.67020(17) 0.71916(14) -0.15622(7) 0.0219(3) Uani 1 1 d .
N2 N 0.68893(17) 0.69256(14) -0.08121(7) 0.0221(3) Uani 1 1 d .
H2A H 0.7869 0.6494 -0.0658 0.027 Uiso 1 1 calc R
N3 N 0.69907(17) 0.62583(14) 0.07531(7) 0.0220(3) Uani 1 1 d .
N4 N 0.10992(17) 0.85656(14) 0.11443(7) 0.0236(3) Uani 1 1 d .
O1 O 0.92292(14) 0.70067(11) -0.32025(6) 0.0221(2) Uani 1 1 d .
O2 O 0.82732(14) 0.58002(12) 0.03382(6) 0.0258(2) Uani 1 1 d .
O3 O 0.69045(16) 0.60571(14) 0.14188(6) 0.0363(3) Uani 1 1 d .
O4 O 0.11208(15) 0.82013(13) 0.17780(6) 0.0285(2) Uani 1 1 d .
O5 O -0.01794(16) 0.92316(13) 0.08979(7) 0.0321(3) Uani 1 1 d .
C1 C -0.0061(2) 0.1872(2) -0.39632(11) 0.0378(4) Uani 1 1 d .
H1B H -0.0270 0.1766 -0.3430 0.057 Uiso 1 1 calc R
H1C H 0.0608 0.1024 -0.4230 0.057 Uiso 1 1 calc R
H1D H -0.1298 0.1848 -0.4264 0.057 Uiso 1 1 calc R
C2 C 0.1131(2) 0.33698(18) -0.39098(9) 0.0250(3) Uani 1 1 d .
H2B H 0.0552 0.4301 -0.3644 0.030 Uiso 1 1 calc R
C3 C 0.2334(2) 0.35899(19) -0.45597(9) 0.0272(3) Uani 1 1 d .
H3A H 0.2429 0.4604 -0.4690 0.033 Uiso 1 1 calc R
H3B H 0.2346 0.2702 -0.5015 0.033 Uiso 1 1 calc R
C4 C 0.3273(2) 0.34994(18) -0.37718(9) 0.0245(3) Uani 1 1 d .
H4A H 0.3806 0.2512 -0.3769 0.029 Uiso 1 1 calc R
C5 C 0.4369(2) 0.48950(18) -0.32145(8) 0.0240(3) Uani 1 1 d .
H5A H 0.4433 0.4739 -0.2672 0.029 Uiso 1 1 calc R
H5B H 0.3666 0.5793 -0.3219 0.029 Uiso 1 1 calc R
C6 C 0.6400(2) 0.52442(17) -0.34227(8) 0.0225(3) Uani 1 1 d .
H6A H 0.7125 0.4370 -0.3390 0.027 Uiso 1 1 calc R
H6B H 0.6340 0.5347 -0.3975 0.027 Uiso 1 1 calc R
C7 C 0.7467(2) 0.67066(17) -0.28807(8) 0.0204(3) Uani 1 1 d .
H7A H 0.6688 0.7577 -0.2881 0.025 Uiso 1 1 calc R
C8 C 1.0191(2) 0.84887(17) -0.28322(9) 0.0261(3) Uani 1 1 d .
H8A H 1.0529 0.8560 -0.2264 0.031 Uiso 1 1 calc R
H8B H 0.9335 0.9279 -0.2877 0.031 Uiso 1 1 calc R
C9 C 1.1980(2) 0.87741(16) -0.32192(8) 0.0217(3) Uani 1 1 d .
C10 C 1.2194(2) 0.79747(17) -0.39812(9) 0.0241(3) Uani 1 1 d .
H10A H 1.1207 0.7213 -0.4268 0.029 Uiso 1 1 calc R
C11 C 1.3858(2) 0.82892(18) -0.43255(9) 0.0278(3) Uani 1 1 d .
H11A H 1.4009 0.7728 -0.4845 0.033 Uiso 1 1 calc R
C12 C 1.5291(2) 0.94126(18) -0.39171(10) 0.0290(4) Uani 1 1 d .
H12A H 1.6417 0.9630 -0.4156 0.035 Uiso 1 1 calc R
C13 C 1.5074(2) 1.02180(18) -0.31581(10) 0.0298(4) Uani 1 1 d .
H13A H 1.6052 1.0993 -0.2875 0.036 Uiso 1 1 calc R
C14 C 1.3431(2) 0.98948(17) -0.28105(9) 0.0276(3) Uani 1 1 d .
H14A H 1.3295 1.0445 -0.2288 0.033 Uiso 1 1 calc R
C15 C 0.7832(2) 0.65378(16) -0.20447(8) 0.0199(3) Uani 1 1 d .
C16 C 0.9338(2) 0.55755(18) -0.18593(9) 0.0277(3) Uani 1 1 d .
H16A H 1.0195 0.6158 -0.1397 0.042 Uiso 1 1 calc R
H16B H 1.0079 0.5300 -0.2313 0.042 Uiso 1 1 calc R
H16C H 0.8726 0.4639 -0.1746 0.042 Uiso 1 1 calc R
C17 C 0.5532(2) 0.73448(16) -0.03226(8) 0.0196(3) Uani 1 1 d .
C18 C 0.55314(19) 0.70418(16) 0.04367(8) 0.0191(3) Uani 1 1 d .
C19 C 0.4083(2) 0.74577(16) 0.09171(8) 0.0197(3) Uani 1 1 d .
H19A H 0.4099 0.7244 0.1424 0.024 Uiso 1 1 calc R
C20 C 0.2635(2) 0.81788(16) 0.06493(8) 0.0208(3) Uani 1 1 d .
C21 C 0.2590(2) 0.85083(17) -0.00909(8) 0.0239(3) Uani 1 1 d .
H21A H 0.1582 0.9017 -0.0265 0.029 Uiso 1 1 calc R
C22 C 0.4001(2) 0.80967(17) -0.05657(9) 0.0239(3) Uani 1 1 d .
H22A H 0.3954 0.8320 -0.1071 0.029 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
C15 N1 N2 115.66(12)
C17 N2 N1 118.58(12)
O3 N3 O2 122.29(12)
O3 N3 C18 118.70(12)
O2 N3 C18 119.01(11)
O4 N4 O5 123.27(12)
O4 N4 C20 118.81(12)
O5 N4 C20 117.92(12)
C8 O1 C7 112.11(10)
C1 C2 C4 120.41(14)
C1 C2 C3 121.15(14)
C4 C2 C3 60.17(10)
C2 C3 C4 59.68(9)
C2 C4 C5 120.24(13)
C2 C4 C3 60.15(10)
C5 C4 C3 120.91(13)
C4 C5 C6 113.17(12)
C7 C6 C5 112.89(12)
O1 C7 C15 110.97(11)
O1 C7 C6 107.02(11)
C15 C7 C6 111.38(12)
O1 C8 C9 109.89(12)
C10 C9 C14 119.24(14)
C10 C9 C8 121.58(13)
C14 C9 C8 119.16(13)
C9 C10 C11 119.97(14)
C12 C11 C10 120.47(15)
C11 C12 C13 119.63(14)
C12 C13 C14 120.03(15)
C13 C14 C9 120.66(15)
N1 C15 C16 125.98(13)
N1 C15 C7 114.77(12)
C16 C15 C7 119.13(12)
N2 C17 C18 122.92(13)
N2 C17 C22 120.22(13)
C18 C17 C22 116.86(12)
C19 C18 C17 121.31(13)
C19 C18 N3 116.06(12)
C17 C18 N3 122.61(12)
C20 C19 C18 119.23(13)
C19 C20 C21 121.27(13)
C19 C20 N4 118.83(13)
C21 C20 N4 119.88(13)
C22 C21 C20 119.75(14)
C21 C22 C17 121.58(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C15 1.2859(18)
N1 N2 1.3875(16)
N2 C17 1.3542(17)
N3 O3 1.2252(15)
N3 O2 1.2430(15)
N3 C18 1.4491(17)
N4 O4 1.2275(15)
N4 O5 1.2348(15)
N4 C20 1.4549(18)
O1 C8 1.4213(17)
O1 C7 1.4299(16)
C1 C2 1.500(2)
C2 C4 1.500(2)
C2 C3 1.507(2)
C3 C4 1.507(2)
C4 C5 1.502(2)
C5 C6 1.5252(19)
C6 C7 1.524(2)
C7 C15 1.5114(19)
C8 C9 1.504(2)
C9 C10 1.386(2)
C9 C14 1.390(2)
C10 C11 1.393(2)
C11 C12 1.383(2)
C12 C13 1.384(2)
C13 C14 1.386(2)
C15 C16 1.497(2)
C17 C18 1.4177(19)
C17 C22 1.418(2)
C18 C19 1.3943(19)
C19 C20 1.3716(19)
C20 C21 1.394(2)
C21 C22 1.366(2)
