#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:08:48 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180062 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/08/7050831.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_7050831
loop_
_publ_author_name
'Pérez, José'
'García, Luis'
'Guy Orpen, A.'
'Dolores Santana, M.'
'Saez, Paloma'
'García, Gabriel'
_publ_section_title
;
 Conformational analysis of complexes of
 2,4,4-trimethyl-1,5,9-triazacyclododec-1-ene and its 9-methyl
 derivative
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              726
_journal_paper_doi               10.1039/b200164k
_journal_volume                  26
_journal_year                    2002
_chemical_formula_sum            'C19 H33 F6 N4 Ni O P'
_chemical_formula_weight         537.17
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.628(7)
_cell_angle_beta                 95.446(7)
_cell_angle_gamma                97.430(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2990(9)
_cell_length_b                   10.5724(10)
_cell_length_c                   12.8248(13)
_cell_measurement_reflns_used    64
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.307
_cell_measurement_theta_min      4.791
_cell_volume                     1172.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.000
_diffrn_measured_fraction_theta_max 0.978
_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  0.0500
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4263
_diffrn_reflns_theta_full        0.50
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.985
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0740
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1375P)²+0.4896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2570
_reflns_number_gt                2661
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b200164k.txt
_cod_data_source_block           6me1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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-1
_cod_database_code               7050831
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.71870(10) 0.69468(9) 0.69915(8) 0.0301(3) Uani 1 1 d . . .
P1 P 0.3510(3) 0.1802(3) 0.8101(2) 0.0582(7) Uani 1 1 d . . .
O1 O 0.8340(6) 0.5861(6) 0.5838(4) 0.0414(13) Uani 1 1 d . . .
N4 N 0.8183(7) 0.5424(6) 0.7416(5) 0.0350(15) Uani 1 1 d . . .
C16 C 0.9882(9) 0.3444(9) 0.6850(7) 0.045(2) Uani 1 1 d . . .
H16 H 1.0478 0.2761 0.6675 0.054 Uiso 1 1 calc R . .
C18 C 0.8721(8) 0.5140(8) 0.6448(6) 0.0361(18) Uani 1 1 d . . .
C15 C 0.9299(9) 0.3739(9) 0.7826(7) 0.044(2) Uani 1 1 d . . .
H15 H 0.9476 0.3238 0.8308 0.053 Uiso 1 1 calc R . .
C14 C 0.8458(10) 0.4753(9) 0.8124(8) 0.046(2) Uani 1 1 d . . .
C17 C 0.9609(9) 0.4130(8) 0.6120(7) 0.043(2) Uani 1 1 d . . .
H17 H 0.9994 0.3936 0.5436 0.051 Uiso 1 1 calc R . .
N3 N 0.8706(6) 0.8725(6) 0.7639(5) 0.0326(14) Uani 1 1 d . . .
N2 N 0.5724(6) 0.7312(6) 0.8071(5) 0.0282(13) Uani 1 1 d . . .
H2 H 0.5963 0.6892 0.8585 0.034 Uiso 1 1 calc R . .
N1 N 0.6011(7) 0.7658(6) 0.5963(5) 0.0320(14) Uani 1 1 d . . .
C3 C 0.4260(8) 0.6536(8) 0.7415(7) 0.0352(17) Uani 1 1 d . . .
C2 C 0.3679(8) 0.7267(8) 0.6624(7) 0.0369(18) Uani 1 1 d . . .
H2A H 0.2800 0.6662 0.6136 0.044 Uiso 1 1 calc R . .
H2B H 0.3343 0.8086 0.7091 0.044 Uiso 1 1 calc R . .
C1 C 0.4650(9) 0.7701(7) 0.5889(6) 0.0355(18) Uani 1 1 d . . .
C13 C 1.0013(8) 0.8410(9) 0.8218(7) 0.043(2) Uani 1 1 d . . .
H13A H 1.0372 0.7657 0.7699 0.064 Uiso 1 1 calc R . .
H13B H 0.9739 0.8158 0.8853 0.064 Uiso 1 1 calc R . .
H13C H 1.0787 0.9210 0.8481 0.064 Uiso 1 1 calc R . .
C12 C 0.4481(10) 0.5119(8) 0.6726(7) 0.043(2) Uani 1 1 d . . .
H12A H 0.5211 0.5193 0.6235 0.064 Uiso 1 1 calc R . .
H12B H 0.3550 0.4607 0.6276 0.064 Uiso 1 1 calc R . .
H12C H 0.4825 0.4649 0.7223 0.064 Uiso 1 1 calc R . .
C11 C 0.3114(9) 0.6433(9) 0.8191(8) 0.047(2) Uani 1 1 d . . .
H11A H 0.3469 0.5989 0.8706 0.071 Uiso 1 1 calc R . .
H11B H 0.2188 0.5902 0.7746 0.071 Uiso 1 1 calc R . .
H11C H 0.2958 0.7344 0.8615 0.071 Uiso 1 1 calc R . .
C6 C 0.8163(9) 0.9879(8) 0.8428(7) 0.041(2) Uani 1 1 d . . .
H6A H 0.7548 1.0286 0.7993 0.050 Uiso 1 1 calc R . .
H6B H 0.9015 1.0579 0.8850 0.050 Uiso 1 1 calc R . .
C10 C 0.3826(10) 0.8232(10) 0.5079(8) 0.054(2) Uani 1 1 d . . .
H10A H 0.4502 0.8505 0.4618 0.081 Uiso 1 1 calc R . .
H10B H 0.3409 0.9016 0.5495 0.081 Uiso 1 1 calc R . .
H10C H 0.3035 0.7519 0.4602 0.081 Uiso 1 1 calc R . .
C5 C 0.7274(9) 0.9485(8) 0.9249(6) 0.0388(19) Uani 1 1 d . . .
H5A H 0.7216 1.0313 0.9871 0.047 Uiso 1 1 calc R . .
H5B H 0.7792 0.8895 0.9562 0.047 Uiso 1 1 calc R . .
C8 C 0.8043(10) 0.9372(9) 0.5917(7) 0.047(2) Uani 1 1 d . . .
H8A H 0.7513 1.0065 0.6358 0.056 Uiso 1 1 calc R . .
H8B H 0.8521 0.9747 0.5397 0.056 Uiso 1 1 calc R . .
C4 C 0.5722(9) 0.8745(8) 0.8727(7) 0.0417(19) Uani 1 1 d . . .
H4A H 0.5104 0.8787 0.9320 0.050 Uiso 1 1 calc R . .
H4B H 0.5295 0.9201 0.8237 0.050 Uiso 1 1 calc R . .
C7 C 0.9250(9) 0.9142(9) 0.6718(7) 0.046(2) Uani 1 1 d . . .
H7A H 0.9768 0.8435 0.6283 0.055 Uiso 1 1 calc R . .
H7B H 0.9972 0.9989 0.7048 0.055 Uiso 1 1 calc R . .
C9 C 0.6940(9) 0.8142(8) 0.5247(6) 0.0399(19) Uani 1 1 d . . .
H9A H 0.6311 0.8364 0.4685 0.048 Uiso 1 1 calc R . .
H9B H 0.7458 0.7412 0.4849 0.048 Uiso 1 1 calc R . .
C19 C 0.7797(12) 0.5134(11) 0.9184(8) 0.063(3) Uani 1 1 d . . .
H19A H 0.7262 0.5883 0.9219 0.094 Uiso 1 1 calc R . .
H19B H 0.8577 0.5415 0.9822 0.094 Uiso 1 1 calc R . .
H19C H 0.7120 0.4352 0.9202 0.094 Uiso 1 1 calc R . .
F1 F 0.3246(8) 0.0375(7) 0.8204(8) 0.099(3) Uani 1 1 d . . .
F2 F 0.1949(9) 0.1954(7) 0.8629(6) 0.096(2) Uani 1 1 d . . .
F3 F 0.2467(8) 0.1271(12) 0.6955(7) 0.130(4) Uani 1 1 d . . .
F4 F 0.4857(8) 0.1616(12) 0.7533(8) 0.136(4) Uani 1 1 d . . .
F5 F 0.4353(11) 0.2386(11) 0.9274(7) 0.155(5) Uani 1 1 d . . .
F6 F 0.3532(14) 0.3199(11) 0.8015(13) 0.183(6) Uani 1 1 d . . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
_geom_angle_publ_flag
N1 Ni1 N2 90.8(2) . . ?
N1 Ni1 O1 96.9(2) . . ?
N2 Ni1 O1 158.7(2) . . ?
N1 Ni1 N3 93.3(2) . . ?
N2 Ni1 N3 101.0(2) . . ?
O1 Ni1 N3 98.3(2) . . ?
N1 Ni1 N4 154.2(2) . . ?
N2 Ni1 N4 101.5(2) . . ?
O1 Ni1 N4 64.2(2) . . ?
N3 Ni1 N4 106.2(2) . . ?
N1 Ni1 C18 126.8(3) . . ?
N2 Ni1 C18 132.5(3) . . ?
O1 Ni1 C18 31.7(2) . . ?
N3 Ni1 C18 103.9(2) . . ?
N4 Ni1 C18 32.6(2) . . ?
F4 P1 F6 91.8(6) . . ?
F4 P1 F5 95.0(6) . . ?
F6 P1 F5 91.8(7) . . ?
F4 P1 F1 96.0(5) . . ?
F6 P1 F1 171.6(6) . . ?
F5 P1 F1 90.7(5) . . ?
F4 P1 F3 92.0(5) . . ?
F6 P1 F3 86.0(7) . . ?
F5 P1 F3 172.7(6) . . ?
F1 P1 F3 90.5(5) . . ?
F4 P1 F2 175.6(5) . . ?
F6 P1 F2 88.2(6) . . ?
F5 P1 F2 89.4(5) . . ?
F1 P1 F2 83.8(4) . . ?
F3 P1 F2 83.6(4) . . ?
C18 O1 Ni1 93.2(4) . . ?
C18 N4 C14 121.4(7) . . ?
C18 N4 Ni1 88.1(5) . . ?
C14 N4 Ni1 150.5(6) . . ?
C15 C16 C17 120.6(8) . . ?
O1 C18 N4 114.4(6) . . ?
O1 C18 C17 123.5(7) . . ?
N4 C18 C17 122.1(8) . . ?
O1 C18 Ni1 55.1(3) . . ?
N4 C18 Ni1 59.3(4) . . ?
C17 C18 Ni1 178.5(7) . . ?
C16 C15 C14 121.4(8) . . ?
N4 C14 C15 118.4(8) . . ?
N4 C14 C19 117.5(8) . . ?
C15 C14 C19 124.1(9) . . ?
C16 C17 C18 116.1(8) . . ?
C13 N3 C7 105.2(6) . . ?
C13 N3 C6 109.5(6) . . ?
C7 N3 C6 109.6(6) . . ?
C13 N3 Ni1 107.3(5) . . ?
C7 N3 Ni1 110.2(5) . . ?
C6 N3 Ni1 114.6(5) . . ?
C4 N2 C3 115.0(6) . . ?
C4 N2 Ni1 117.0(5) . . ?
C3 N2 Ni1 105.8(4) . . ?
C1 N1 C9 121.4(7) . . ?
C1 N1 Ni1 127.2(6) . . ?
C9 N1 Ni1 111.4(5) . . ?
N2 C3 C12 108.1(6) . . ?
N2 C3 C11 111.3(7) . . ?
C12 C3 C11 110.0(7) . . ?
N2 C3 C2 109.9(6) . . ?
C12 C3 C2 109.4(7) . . ?
C11 C3 C2 108.3(6) . . ?
C1 C2 C3 120.6(6) . . ?
N1 C1 C2 123.2(7) . . ?
N1 C1 C10 124.4(8) . . ?
C2 C1 C10 112.4(7) . . ?
N3 C6 C5 114.2(7) . . ?
C6 C5 C4 113.2(7) . . ?
C9 C8 C7 115.8(7) . . ?
N2 C4 C5 111.1(6) . . ?
N3 C7 C8 114.6(7) . . ?
N1 C9 C8 111.4(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.018(6) . ?
Ni1 N2 2.017(6) . ?
Ni1 O1 2.047(5) . ?
Ni1 N3 2.077(6) . ?
Ni1 N4 2.144(6) . ?
Ni1 C18 2.492(7) . ?
P1 F4 1.511(8) . ?
P1 F6 1.514(9) . ?
P1 F5 1.522(8) . ?
P1 F1 1.546(7) . ?
P1 F3 1.574(8) . ?
P1 F2 1.664(7) . ?
O1 C18 1.310(9) . ?
N4 C18 1.342(10) . ?
N4 C14 1.345(11) . ?
C16 C15 1.372(12) . ?
C16 C17 1.380(12) . ?
C18 C17 1.417(11) . ?
C15 C14 1.385(12) . ?
C14 C19 1.504(13) . ?
N3 C13 1.493(9) . ?
N3 C7 1.494(10) . ?
N3 C6 1.495(10) . ?
N2 C4 1.479(9) . ?
N2 C3 1.513(9) . ?
N1 C1 1.269(10) . ?
N1 C9 1.478(10) . ?
C3 C12 1.529(10) . ?
C3 C11 1.542(11) . ?
C3 C2 1.557(11) . ?
C2 C1 1.498(12) . ?
C1 C10 1.522(11) . ?
C6 C5 1.524(11) . ?
C5 C4 1.528(11) . ?
C8 C9 1.502(11) . ?
C8 C7 1.545(12) . ?
