#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:03:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179522 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/19/4341962.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_4341962
loop_
_publ_author_name
'Wilson, Justin J.'
'Birnbaum, Eva R.'
'Batista, Enrique R.'
'Martin, Richard L.'
'John, Kevin D.'
_publ_section_title
;
 Synthesis and Characterization of Nitrogen-Rich Macrocyclic Ligands and
 an Investigation of Their Coordination Chemistry with Lanthanum(III).
;
_journal_issue                   1
_journal_name_full               'Inorganic chemistry'
_journal_page_first              97
_journal_page_last               109
_journal_paper_doi               10.1021/ic501843c
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C28 H36 N12'
_chemical_formula_weight         540.69
_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                 99.7720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6230(15)
_cell_length_b                   10.0308(13)
_cell_length_c                   11.6987(15)
_cell_measurement_temperature    140(1)
_cell_volume                     1344.1(3)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω 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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14616
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0369
_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)+(0.0493P)²+0.5377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                2718
_reflns_number_total             3055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501843c_si_002.cif
_cod_data_source_block           Lpz
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4341960--4341964.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4341962
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
N1 N 0.29576(7) 0.57680(9) 0.51394(7) 0.0142(2) Uani 1 1 d .
N3 N 0.04450(8) 0.71738(10) 0.59620(8) 0.0187(2) Uani 1 1 d .
N2 N 0.57247(7) 0.66825(9) 0.59068(7) 0.01427(19) Uani 1 1 d .
N4 N 0.05557(8) 0.50862(10) 0.75695(8) 0.0208(2) Uani 1 1 d .
C3 C 0.66958(9) 0.58096(11) 0.64220(9) 0.0157(2) Uani 1 1 d .
H3A H 0.6732 0.5778 0.7256 0.019 Uiso 1 1 calc R
H3B H 0.7426 0.6179 0.6269 0.019 Uiso 1 1 calc R
C1 C 0.35343(9) 0.68712(11) 0.58432(9) 0.0158(2) Uani 1 1 d .
H1A H 0.3042 0.7162 0.6387 0.019 Uiso 1 1 calc R
H1B H 0.3632 0.7617 0.5341 0.019 Uiso 1 1 calc R
C2 C 0.47262(9) 0.64592(11) 0.65114(9) 0.0158(2) Uani 1 1 d .
H2A H 0.4866 0.6946 0.7238 0.019 Uiso 1 1 calc R
H2B H 0.4697 0.5519 0.6698 0.019 Uiso 1 1 calc R
N6 N 0.79674(9) 0.81549(10) 0.37190(8) 0.0208(2) Uani 1 1 d .
C7 C 0.11354(10) 0.50512(11) 0.66803(10) 0.0188(2) Uani 1 1 d .
H7 H 0.1595 0.4311 0.6596 0.023 Uiso 1 1 calc R
C9 C -0.01354(10) 0.72071(12) 0.68582(10) 0.0206(2) Uani 1 1 d .
H9 H -0.0588 0.7951 0.6951 0.025 Uiso 1 1 calc R
C6 C 0.10809(9) 0.60813(11) 0.58687(9) 0.0162(2) Uani 1 1 d .
C8 C -0.00855(9) 0.61796(12) 0.76466(10) 0.0205(2) Uani 1 1 d .
H8 H -0.0510 0.6248 0.8250 0.025 Uiso 1 1 calc R
N5 N 0.74700(8) 0.96715(10) 0.55870(8) 0.0200(2) Uani 1 1 d .
C13 C 0.82370(11) 1.00716(12) 0.49277(11) 0.0225(3) Uani 1 1 d .
H13 H 0.8621 1.0880 0.5095 0.027 Uiso 1 1 calc R
C10 C 0.60660(9) 0.80814(11) 0.60381(9) 0.0167(2) Uani 1 1 d .
H10A H 0.6389 0.8247 0.6846 0.020 Uiso 1 1 calc R
H10B H 0.5374 0.8630 0.5840 0.020 Uiso 1 1 calc R
C14 C 0.84787(10) 0.93245(12) 0.40063(11) 0.0225(3) Uani 1 1 d .
H14 H 0.9017 0.9649 0.3571 0.027 Uiso 1 1 calc R
C12 C 0.72001(10) 0.77511(11) 0.43761(9) 0.0174(2) Uani 1 1 d .
H12 H 0.6823 0.6939 0.4209 0.021 Uiso 1 1 calc R
C11 C 0.69440(9) 0.85026(11) 0.53038(9) 0.0156(2) Uani 1 1 d .
C4 C 0.34503(9) 0.55995(11) 0.40675(9) 0.0152(2) Uani 1 1 d .
H4A H 0.4275 0.5818 0.4226 0.018 Uiso 1 1 calc R
H4B H 0.3072 0.6221 0.3488 0.018 Uiso 1 1 calc R
C5 C 0.16968(9) 0.59988(11) 0.48347(9) 0.0170(2) Uani 1 1 d .
H5A H 0.1353 0.5282 0.4334 0.020 Uiso 1 1 calc R
H5B H 0.1567 0.6824 0.4399 0.020 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'
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_1
_geom_angle_site_symmetry_3
C5 N1 C1 111.03(8) . .
C5 N1 C4 109.13(8) . .
C1 N1 C4 110.88(8) . .
C9 N3 C6 116.31(10) . .
C10 N2 C3 110.65(8) . .
C10 N2 C2 108.51(8) . .
C3 N2 C2 108.89(8) . .
C8 N4 C7 115.82(10) . .
N2 C3 C4 111.63(8) . 3_666
N2 C3 H3A 109.3 . .
C4 C3 H3A 109.3 3_666 .
N2 C3 H3B 109.3 . .
C4 C3 H3B 109.3 3_666 .
H3A C3 H3B 108.0 . .
N1 C1 C2 111.74(9) . .
N1 C1 H1A 109.3 . .
C2 C1 H1A 109.3 . .
N1 C1 H1B 109.3 . .
C2 C1 H1B 109.3 . .
H1A C1 H1B 107.9 . .
N2 C2 C1 115.62(9) . .
N2 C2 H2A 108.4 . .
C1 C2 H2A 108.4 . .
N2 C2 H2B 108.4 . .
C1 C2 H2B 108.4 . .
H2A C2 H2B 107.4 . .
C14 N6 C12 115.77(10) . .
N4 C7 C6 122.71(10) . .
N4 C7 H7 118.6 . .
C6 C7 H7 118.6 . .
N3 C9 C8 122.38(11) . .
N3 C9 H9 118.8 . .
C8 C9 H9 118.8 . .
N3 C6 C7 120.84(10) . .
N3 C6 C5 117.04(10) . .
C7 C6 C5 122.09(10) . .
N4 C8 C9 121.93(10) . .
N4 C8 H8 119.0 . .
C9 C8 H8 119.0 . .
C13 N5 C11 116.24(10) . .
N5 C13 C14 122.14(11) . .
N5 C13 H13 118.9 . .
C14 C13 H13 118.9 . .
N2 C10 C11 114.16(9) . .
N2 C10 H10A 108.7 . .
C11 C10 H10A 108.7 . .
N2 C10 H10B 108.7 . .
C11 C10 H10B 108.7 . .
H10A C10 H10B 107.6 . .
N6 C14 C13 122.27(11) . .
N6 C14 H14 118.9 . .
C13 C14 H14 118.9 . .
N6 C12 C11 122.39(10) . .
N6 C12 H12 118.8 . .
C11 C12 H12 118.8 . .
N5 C11 C12 121.18(10) . .
N5 C11 C10 115.54(9) . .
C12 C11 C10 123.27(10) . .
N1 C4 C3 113.05(9) . 3_666
N1 C4 H4A 109.0 . .
C3 C4 H4A 109.0 3_666 .
N1 C4 H4B 109.0 . .
C3 C4 H4B 109.0 3_666 .
H4A C4 H4B 107.8 . .
N1 C5 C6 113.84(9) . .
N1 C5 H5A 108.8 . .
C6 C5 H5A 108.8 . .
N1 C5 H5B 108.8 . .
C6 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.4666(13) .
N1 C1 1.4711(13) .
N1 C4 1.4741(13) .
N3 C9 1.3400(14) .
N3 C6 1.3366(14) .
N2 C10 1.4592(14) .
N2 C3 1.4741(13) .
N2 C2 1.4752(13) .
N4 C8 1.3377(15) .
N4 C7 1.3324(14) .
C3 C4 1.5237(15) 3_666
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C1 C2 1.5276(15) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
N6 C14 1.3322(16) .
N6 C12 1.3353(14) .
C7 C6 1.3975(16) .
C7 H7 0.9300 .
C9 C8 1.3778(17) .
C9 H9 0.9300 .
C6 C5 1.5087(14) .
C8 H8 0.9300 .
N5 C13 1.3357(15) .
N5 C11 1.3377(15) .
C13 C14 1.3803(17) .
C13 H13 0.9300 .
C10 C11 1.5019(15) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C14 H14 0.9300 .
C12 C11 1.3944(15) .
C12 H12 0.9300 .
C4 C3 1.5237(15) 3_666
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
