#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:03:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179522 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/19/4341960.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_4341960
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           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                106.408(4)
_cell_angle_beta                 91.713(4)
_cell_angle_gamma                115.409(4)
_cell_formula_units_Z            1
_cell_length_a                   8.8576(5)
_cell_length_b                   9.6141(6)
_cell_length_c                   9.6564(6)
_cell_measurement_reflns_used    4219
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.74
_cell_volume                     701.61(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16845
_diffrn_reflns_theta_full        28.87
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9983
_exptl_absorpt_correction_T_min  0.9796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing, 1995'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0509
_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)+(0.0347P)²+0.2883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2471
_reflns_number_total             3637
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501843c_si_002.cif
_cod_data_source_block           Lpyd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

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_cell_volume        701.61(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4341960
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 0.14460(16) 0.74167(14) 0.58078(14) 0.0137(3) Uani 1 1 d .
N3 N 0.25090(18) 1.01946(15) 0.40009(15) 0.0190(3) Uani 1 1 d .
N2 N -0.21741(16) 0.55014(14) 0.37642(14) 0.0138(3) Uani 1 1 d .
N5 N -0.40886(18) 0.68878(16) 0.13780(15) 0.0198(3) Uani 1 1 d .
C6 C 0.27592(19) 0.89703(17) 0.41632(17) 0.0146(3) Uani 1 1 d .
C2 C -0.16889(19) 0.60177(17) 0.53650(16) 0.0146(3) Uani 1 1 d .
H2A H -0.1484 0.5183 0.5629 0.017 Uiso 1 1 calc R
H2B H -0.2629 0.6117 0.5841 0.017 Uiso 1 1 calc R
C10 C -0.3156(2) 0.62711(18) 0.33750(17) 0.0165(3) Uani 1 1 d .
H10A H -0.2801 0.7339 0.4141 0.020 Uiso 1 1 calc R
H10B H -0.4372 0.5584 0.3360 0.020 Uiso 1 1 calc R
N4 N 0.25351(18) 1.04350(16) 0.26876(15) 0.0219(3) Uani 1 1 d .
C11 C -0.2949(2) 0.65241(17) 0.19107(17) 0.0151(3) Uani 1 1 d .
N6 N -0.39617(19) 0.72432(17) 0.01189(15) 0.0234(3) Uani 1 1 d .
C7 C 0.3016(2) 0.78834(18) 0.30013(18) 0.0186(3) Uani 1 1 d .
H7 H 0.3155 0.6999 0.3131 0.022 Uiso 1 1 calc R
C5 C 0.2860(2) 0.88808(17) 0.56885(17) 0.0160(3) Uani 1 1 d .
H5A H 0.3944 0.8883 0.5973 0.019 Uiso 1 1 calc R
H5B H 0.2852 0.9858 0.6379 0.019 Uiso 1 1 calc R
C3 C -0.3082(2) 0.37259(17) 0.30629(17) 0.0156(3) Uani 1 1 d .
H3A H -0.3699 0.3473 0.2082 0.019 Uiso 1 1 calc R
H3B H -0.3932 0.3252 0.3655 0.019 Uiso 1 1 calc R
C1 C -0.00962(19) 0.76428(17) 0.59195(17) 0.0152(3) Uani 1 1 d .
H1A H -0.0110 0.8337 0.5338 0.018 Uiso 1 1 calc R
H1B H -0.0080 0.8207 0.6955 0.018 Uiso 1 1 calc R
C4 C 0.1897(2) 0.70666(18) 0.71026(17) 0.0159(3) Uani 1 1 d .
H4A H 0.0837 0.6341 0.7361 0.019 Uiso 1 1 calc R
H4B H 0.2440 0.8101 0.7934 0.019 Uiso 1 1 calc R
C9 C 0.2821(2) 0.94448(19) 0.15774(18) 0.0211(4) Uani 1 1 d .
H9 H 0.2864 0.9643 0.0666 0.025 Uiso 1 1 calc R
C8 C 0.3061(2) 0.81313(19) 0.16738(18) 0.0205(4) Uani 1 1 d .
H8 H 0.3247 0.7439 0.0853 0.025 Uiso 1 1 calc R
C12 C -0.1627(2) 0.6460(2) 0.11950(19) 0.0221(4) Uani 1 1 d .
H12 H -0.0832 0.6191 0.1587 0.026 Uiso 1 1 calc R
C14 C -0.2712(2) 0.71946(19) -0.05928(18) 0.0223(4) Uani 1 1 d .
H14 H -0.2638 0.7441 -0.1482 0.027 Uiso 1 1 calc R
C13 C -0.1512(2) 0.6800(2) -0.00931(19) 0.0263(4) Uani 1 1 d .
H13 H -0.0639 0.6767 -0.0628 0.032 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 C4 109.84(12) . .
C5 N1 C1 110.40(11) . .
C4 N1 C1 109.83(12) . .
C6 N3 N4 119.89(13) . .
C10 N2 C3 110.65(12) . .
C10 N2 C2 110.82(12) . .
C3 N2 C2 113.68(11) . .
C11 N5 N6 119.93(14) . .
N3 C6 C7 122.26(14) . .
N3 C6 C5 116.29(13) . .
C7 C6 C5 121.35(14) . .
N2 C2 C1 110.74(12) . .
N2 C2 H2A 109.5 . .
C1 C2 H2A 109.5 . .
N2 C2 H2B 109.5 . .
C1 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
N2 C10 C11 113.32(13) . .
N2 C10 H10A 108.9 . .
C11 C10 H10A 108.9 . .
N2 C10 H10B 108.9 . .
C11 C10 H10B 108.9 . .
H10A C10 H10B 107.7 . .
C9 N4 N3 118.96(13) . .
N5 C11 C12 122.35(15) . .
N5 C11 C10 114.72(14) . .
C12 C11 C10 122.86(14) . .
C14 N6 N5 119.26(14) . .
C8 C7 C6 118.06(15) . .
C8 C7 H7 121.0 . .
C6 C7 H7 121.0 . .
N1 C5 C6 112.14(12) . .
N1 C5 H5A 109.2 . .
C6 C5 H5A 109.2 . .
N1 C5 H5B 109.2 . .
C6 C5 H5B 109.2 . .
H5A C5 H5B 107.9 . .
N2 C3 C4 112.66(12) . 2_566
N2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 2_566 .
N2 C3 H3B 109.1 . .
C4 C3 H3B 109.1 2_566 .
H3A C3 H3B 107.8 . .
N1 C1 C2 111.15(12) . .
N1 C1 H1A 109.4 . .
C2 C1 H1A 109.4 . .
N1 C1 H1B 109.4 . .
C2 C1 H1B 109.4 . .
H1A C1 H1B 108.0 . .
N1 C4 C3 115.72(12) . 2_566
N1 C4 H4A 108.4 . .
C3 C4 H4A 108.4 2_566 .
N1 C4 H4B 108.4 . .
C3 C4 H4B 108.4 2_566 .
H4A C4 H4B 107.4 . .
N4 C9 C8 123.72(15) . .
N4 C9 H9 118.1 . .
C8 C9 H9 118.1 . .
C7 C8 C9 117.07(15) . .
C7 C8 H8 121.5 . .
C9 C8 H8 121.5 . .
C13 C12 C11 117.68(16) . .
C13 C12 H12 121.2 . .
C11 C12 H12 121.2 . .
N6 C14 C13 122.88(16) . .
N6 C14 H14 118.6 . .
C13 C14 H14 118.6 . .
C12 C13 C14 117.90(16) . .
C12 C13 H13 121.1 . .
C14 C13 H13 121.1 . .
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(18) .
N1 C4 1.4695(19) .
N1 C1 1.4748(19) .
N3 C6 1.3362(19) .
N3 N4 1.3508(18) .
N2 C10 1.4614(19) .
N2 C3 1.4682(18) .
N2 C2 1.4712(19) .
N5 C11 1.334(2) .
N5 N6 1.3481(19) .
C6 C7 1.400(2) .
C6 C5 1.502(2) .
C2 C1 1.519(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C10 C11 1.505(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
N4 C9 1.329(2) .
C11 C12 1.392(2) .
N6 C14 1.331(2) .
C7 C8 1.367(2) .
C7 H7 0.9500 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C3 C4 1.529(2) 2_566
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C4 C3 1.529(2) 2_566
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C9 C8 1.394(2) .
C9 H9 0.9500 .
C8 H8 0.9500 .
C12 C13 1.368(2) .
C12 H12 0.9500 .
C14 C13 1.388(2) .
C14 H14 0.9500 .
C13 H13 0.9500 .
