#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:37:18 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179453 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/50/4335063.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_4335063
loop_
_publ_author_name
'Peter Comba'
'Michael Morgen'
'Hubert Wadepohl'
_publ_section_title
;
 Tuning of the Properties of Transition-Metal Bispidine Complexes by
 Variation of the Basicity of the Aromatic Donor Groups
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              6481
_journal_page_last               6501
_journal_paper_doi               10.1021/ic4004214
_journal_volume                  52
_journal_year                    2013
_chemical_formula_sum            'C18 H19 N5 O5'
_chemical_formula_weight         385.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                co_mimo34
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.223(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.953(5)
_cell_length_b                   10.320(5)
_cell_length_c                   17.131(8)
_cell_measurement_reflns_used    8181
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.96
_cell_measurement_theta_min      2.30
_cell_volume                     1758.3(15)
_computing_cell_refinement
;
SAINT (Bruker AXS, 1997-2008). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction
'SAINT (Bruker AXS, 1997-2008); SADABS (Bruker AXS, 2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            44215
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         32.23
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_correction_T_min  0.8114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0481
_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)+(0.0657P)²+0.7925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1305
_reflns_number_gt                4539
_reflns_number_total             5920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic4004214_si_004_1.cif
_cod_data_source_block           co_mimo34
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4335063
#BEGIN Tags that were not found in dictionaries:
_audit_block_refno               1334
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.41235(10) 0.84168(9) 0.43587(5) 0.02046(19) Uani 1 1 d .
O2 O 0.50306(9) 0.69670(8) 0.52052(5) 0.01745(18) Uani 1 1 d .
O3 O 0.01357(9) 0.98805(9) 0.59732(5) 0.01925(19) Uani 1 1 d .
O4 O 0.07260(9) 1.19645(8) 0.58129(5) 0.01716(18) Uani 1 1 d .
O5 O 0.29535(9) 1.04138(8) 0.49349(5) 0.01730(18) Uani 1 1 d .
H5 H 0.3269 0.9961 0.4578 0.026 Uiso 1 1 calc R
N1 N 0.37000(10) 0.89251(10) 0.71530(6) 0.01423(19) Uani 1 1 d .
N2 N 0.23548(11) 0.63077(10) 0.59563(6) 0.0166(2) Uani 1 1 d .
N3 N 0.17081(12) 0.54163(11) 0.74398(7) 0.0207(2) Uani 1 1 d .
N4 N 0.19343(13) 1.17621(11) 0.76417(6) 0.0224(2) Uani 1 1 d .
N5 N 0.19562(12) 1.05980(11) 0.91201(6) 0.0214(2) Uani 1 1 d .
C1 C 0.37069(12) 0.86179(11) 0.57131(7) 0.0139(2) Uani 1 1 d .
C2 C 0.38336(12) 0.79931(11) 0.65146(7) 0.0138(2) Uani 1 1 d .
H2 H 0.4758 0.7615 0.6570 0.017 Uiso 1 1 calc R
C4 C 0.24659(12) 0.96856(11) 0.70246(6) 0.0131(2) Uani 1 1 d .
H4 H 0.1710 0.9049 0.6971 0.016 Uiso 1 1 calc R
C5 C 0.24307(12) 1.04902(11) 0.62676(6) 0.0132(2) Uani 1 1 d .
H5A H 0.2898 1.1337 0.6362 0.016 Uiso 1 1 calc R
C6 C 0.30796(12) 0.97739(11) 0.56161(7) 0.0137(2) Uani 1 1 d .
C7 C 0.42864(12) 0.80103(11) 0.50332(7) 0.0150(2) Uani 1 1 d .
C8 C 0.56389(14) 0.63465(13) 0.45491(8) 0.0217(3) Uani 1 1 d .
H8A H 0.4938 0.6115 0.4156 0.033 Uiso 1 1 calc R
H8B H 0.6111 0.5561 0.4728 0.033 Uiso 1 1 calc R
H8C H 0.6279 0.6943 0.4319 0.033 Uiso 1 1 calc R
C9 C 0.09651(12) 1.07276(11) 0.60086(7) 0.0143(2) Uani 1 1 d .
C10 C -0.06461(13) 1.22178(13) 0.55395(8) 0.0218(3) Uani 1 1 d .
H10A H -0.0819 1.1786 0.5036 0.033 Uiso 1 1 calc R
H10B H -0.0778 1.3154 0.5477 0.033 Uiso 1 1 calc R
H10C H -0.1269 1.1885 0.5921 0.033 Uiso 1 1 calc R
C11 C 0.49128(13) 0.97168(12) 0.72730(7) 0.0186(2) Uani 1 1 d .
H11A H 0.5060 1.0228 0.6802 0.028 Uiso 1 1 calc R
H11B H 0.5689 0.9151 0.7381 0.028 Uiso 1 1 calc R
H11C H 0.4800 1.0301 0.7717 0.028 Uiso 1 1 calc R
C12 C 0.28412(12) 0.68844(11) 0.66061(7) 0.0138(2) Uani 1 1 d .
C13 C 0.15597(13) 0.52780(12) 0.60520(8) 0.0187(2) Uani 1 1 d .
H13 H 0.1194 0.4843 0.5603 0.022 Uiso 1 1 calc R
C14 C 0.12544(13) 0.48279(12) 0.67851(8) 0.0193(2) Uani 1 1 d .
H14 H 0.0706 0.4079 0.6825 0.023 Uiso 1 1 calc R
C15 C 0.25004(13) 0.64432(12) 0.73440(7) 0.0175(2) Uani 1 1 d .
H15 H 0.2845 0.6890 0.7793 0.021 Uiso 1 1 calc R
C16 C 0.22005(12) 1.05034(11) 0.77375(7) 0.0146(2) Uani 1 1 d .
C17 C 0.16872(16) 1.24367(13) 0.82929(8) 0.0250(3) Uani 1 1 d .
H17 H 0.1498 1.3337 0.8251 0.030 Uiso 1 1 calc R
C18 C 0.17007(14) 1.18614(13) 0.90190(8) 0.0212(3) Uani 1 1 d .
H18 H 0.1523 1.2378 0.9462 0.025 Uiso 1 1 calc R
C19 C 0.22125(13) 0.99347(12) 0.84745(7) 0.0177(2) Uani 1 1 d .
H19 H 0.2411 0.9037 0.8519 0.021 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
C7 O2 C8 115.56(10)
C9 O4 C10 114.13(10)
C6 O5 H5 109.5
C11 N1 C2 111.86(10)
C11 N1 C4 113.77(10)
C2 N1 C4 109.80(9)
C12 N2 C13 116.63(11)
C15 N3 C14 116.03(11)
C16 N4 C17 116.32(11)
C19 N5 C18 115.73(11)
C6 C1 C7 118.35(11)
C6 C1 C2 120.47(10)
C7 C1 C2 121.15(10)
N1 C2 C1 112.91(10)
N1 C2 C12 109.75(10)
C1 C2 C12 112.37(10)
N1 C2 H2 107.2
C1 C2 H2 107.2
C12 C2 H2 107.2
N1 C4 C16 110.37(9)
N1 C4 C5 113.98(9)
C16 C4 C5 112.30(10)
N1 C4 H4 106.6
C16 C4 H4 106.6
C5 C4 H4 106.6
C6 C5 C9 107.20(9)
C6 C5 C4 111.31(10)
C9 C5 C4 108.75(9)
C6 C5 H5A 109.8
C9 C5 H5A 109.8
C4 C5 H5A 109.8
O5 C6 C1 124.56(11)
O5 C6 C5 112.00(10)
C1 C6 C5 123.44(10)
O1 C7 O2 122.21(11)
O1 C7 C1 123.98(11)
O2 C7 C1 113.80(10)
O2 C8 H8A 109.5
O2 C8 H8B 109.5
H8A C8 H8B 109.5
O2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O3 C9 O4 124.45(12)
O3 C9 C5 122.95(11)
O4 C9 C5 112.58(10)
O4 C10 H10A 109.5
O4 C10 H10B 109.5
H10A C10 H10B 109.5
O4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N1 C11 H11A 109.5
N1 C11 H11B 109.5
H11A C11 H11B 109.5
N1 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 C15 121.03(11)
N2 C12 C2 117.65(10)
C15 C12 C2 121.24(10)
N2 C13 C14 121.95(12)
N2 C13 H13 119.0
C14 C13 H13 119.0
N3 C14 C13 121.97(12)
N3 C14 H14 119.0
C13 C14 H14 119.0
N3 C15 C12 122.35(11)
N3 C15 H15 118.8
C12 C15 H15 118.8
N4 C16 C19 121.11(11)
N4 C16 C4 118.86(10)
C19 C16 C4 120.02(11)
N4 C17 C18 121.99(12)
N4 C17 H17 119.0
C18 C17 H17 119.0
N5 C18 C17 122.12(12)
N5 C18 H18 118.9
C17 C18 H18 118.9
N5 C19 C16 122.73(12)
N5 C19 H19 118.6
C16 C19 H19 118.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2341(15)
O2 C7 1.3333(15)
O2 C8 1.4466(15)
O3 C9 1.2023(15)
O4 C9 1.3387(15)
O4 C10 1.4501(16)
O5 C6 1.3425(14)
O5 H5 0.8400
N1 C11 1.4654(17)
N1 C2 1.4664(16)
N1 C4 1.4669(16)
N2 C12 1.3363(16)
N2 C13 1.3388(16)
N3 C15 1.3349(17)
N3 C14 1.3385(18)
N4 C16 1.3346(16)
N4 C17 1.3457(17)
N5 C19 1.3338(16)
N5 C18 1.3384(18)
C1 C6 1.3537(17)
C1 C7 1.4610(17)
C1 C2 1.5178(17)
C2 C12 1.5236(17)
C2 H2 1.0000
C4 C16 1.5161(16)
C4 C5 1.5392(16)
C4 H4 1.0000
C5 C6 1.5050(16)
C5 C9 1.5279(18)
C5 H5A 1.0000
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C15 1.3977(17)
C13 C14 1.3838(19)
C13 H13 0.9500
C14 H14 0.9500
C15 H15 0.9500
C16 C19 1.3918(17)
C17 C18 1.3779(19)
C17 H17 0.9500
C18 H18 0.9500
C19 H19 0.9500
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
C11 N1 C2 C1 -75.38(12)
C4 N1 C2 C1 51.92(12)
C11 N1 C2 C12 158.40(10)
C4 N1 C2 C12 -74.30(12)
C6 C1 C2 N1 -21.48(15)
C7 C1 C2 N1 156.83(10)
C6 C1 C2 C12 103.33(13)
C7 C1 C2 C12 -78.36(14)
C11 N1 C4 C16 -62.56(12)
C2 N1 C4 C16 171.22(9)
C11 N1 C4 C5 64.90(12)
C2 N1 C4 C5 -61.32(12)
N1 C4 C5 C6 36.95(13)
C16 C4 C5 C6 163.41(10)
N1 C4 C5 C9 154.83(9)
C16 C4 C5 C9 -78.71(12)
C7 C1 C6 O5 -0.29(18)
C2 C1 C6 O5 178.07(10)
C7 C1 C6 C5 179.34(10)
C2 C1 C6 C5 -2.30(18)
C9 C5 C6 O5 55.78(12)
C4 C5 C6 O5 174.60(9)
C9 C5 C6 C1 -123.90(12)
C4 C5 C6 C1 -5.08(16)
C8 O2 C7 O1 0.25(17)
C8 O2 C7 C1 -179.17(10)
C6 C1 C7 O1 -7.73(18)
C2 C1 C7 O1 173.92(11)
C6 C1 C7 O2 171.68(11)
C2 C1 C7 O2 -6.67(16)
C10 O4 C9 O3 -0.53(17)
C10 O4 C9 C5 178.09(10)
C6 C5 C9 O3 72.44(14)
C4 C5 C9 O3 -48.02(14)
C6 C5 C9 O4 -106.21(11)
C4 C5 C9 O4 133.33(10)
C13 N2 C12 C15 -1.56(17)
C13 N2 C12 C2 175.41(10)
N1 C2 C12 N2 149.20(10)
C1 C2 C12 N2 22.68(14)
N1 C2 C12 C15 -33.83(15)
C1 C2 C12 C15 -160.36(11)
C12 N2 C13 C14 -0.06(18)
C15 N3 C14 C13 -1.64(19)
N2 C13 C14 N3 1.8(2)
C14 N3 C15 C12 -0.01(18)
N2 C12 C15 N3 1.68(19)
C2 C12 C15 N3 -175.18(11)
C17 N4 C16 C19 0.24(19)
C17 N4 C16 C4 179.05(12)
N1 C4 C16 N4 130.40(12)
C5 C4 C16 N4 2.02(16)
N1 C4 C16 C19 -50.77(14)
C5 C4 C16 C19 -179.15(11)
C16 N4 C17 C18 -0.3(2)
C19 N5 C18 C17 0.8(2)
N4 C17 C18 N5 -0.2(2)
C18 N5 C19 C16 -0.84(19)
N4 C16 C19 N5 0.4(2)
C4 C16 C19 N5 -178.44(11)
