#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:12:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178553 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/61/4066141.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_4066141
loop_
_publ_author_name
'Alonso-Moreno, Carlos'
'Carrillo-Hermosilla, Fernando'
'Garcés, Andrés'
'Otero, Antonio'
'López-Solera, Isabel'
'Rodríguez, Ana M.'
'Antiñolo, Antonio'
_publ_section_title
;
 Simple, Versatile, and Efficient Catalysts for Guanylation of Amines
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2789
_journal_paper_doi               10.1021/om1003122
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C38 H66 N6 Zn2'
_chemical_formula_weight         737.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.214(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.392(4)
_cell_length_b                   9.546(3)
_cell_length_c                   17.778(5)
_cell_measurement_temperature    230(2)
_cell_volume                     2090.7(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX'
_computing_data_reduction        'Bruker SHELXTL'
_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      230(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scan'
_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  0.0997
_diffrn_reflns_av_sigmaI/netI    0.0754
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5060
_diffrn_reflns_theta_full        16.78
_diffrn_reflns_theta_max         16.78
_diffrn_reflns_theta_min         2.30
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.491542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prismatic
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0448
_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)+(0.0649P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                840
_reflns_number_total             1172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om1003122_si_001.cif
_cod_data_source_block           15
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4066141
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
Zn1 Zn 0.43811(9) 0.12034(11) 1.02864(6) 0.0471(7) Uani 1 1 d .
N1 N 0.6012(11) 0.0873(9) 0.9756(6) 0.044(3) Uani 1 1 d .
N2 N 0.4441(11) 0.1830(8) 0.9197(5) 0.039(2) Uani 1 1 d .
N3 N 0.6037(10) 0.2162(9) 0.8614(7) 0.056(3) Uani 1 1 d .
H3 H 0.560(8) 0.267(9) 0.826(6) 0.067 Uiso 1 1 d .
C1 C 0.4315(9) 0.2389(10) 1.1180(6) 0.073(4) Uani 1 1 d .
H1A H 0.3660 0.2159 1.1407 0.087 Uiso 1 1 calc R
H1B H 0.4928 0.2163 1.1546 0.087 Uiso 1 1 calc R
C2 C 0.4323(8) 0.3975(10) 1.1029(6) 0.076(4) Uani 1 1 d .
H2A H 0.5006 0.4237 1.0862 0.115 Uiso 1 1 calc R
H2B H 0.4224 0.4470 1.1487 0.115 Uiso 1 1 calc R
H2C H 0.3745 0.4208 1.0646 0.115 Uiso 1 1 calc R
C3 C 0.3725(11) 0.2320(12) 0.8555(8) 0.058(3) Uani 1 1 d .
H3A H 0.4130 0.2985 0.8272 0.070 Uiso 1 1 calc R
C4 C 0.3350(8) 0.1157(12) 0.8040(6) 0.070(4) Uani 1 1 d .
H4A H 0.3967 0.0687 0.7874 0.106 Uiso 1 1 calc R
H4B H 0.2906 0.1525 0.7609 0.106 Uiso 1 1 calc R
H4C H 0.2935 0.0505 0.8302 0.106 Uiso 1 1 calc R
C5 C 0.2780(9) 0.3099(11) 0.8842(6) 0.079(4) Uani 1 1 d .
H5A H 0.2365 0.2462 0.9114 0.119 Uiso 1 1 calc R
H5B H 0.2326 0.3485 0.8421 0.119 Uiso 1 1 calc R
H5C H 0.3054 0.3842 0.9174 0.119 Uiso 1 1 calc R
C6 C 0.5480(14) 0.1654(11) 0.9186(9) 0.039(3) Uani 1 1 d .
C7 C 0.7035(12) 0.1631(12) 0.8351(7) 0.060(3) Uani 1 1 d .
H7 H 0.7345 0.0950 0.8726 0.072 Uiso 1 1 calc R
C8 C 0.7831(11) 0.2798(14) 0.8336(8) 0.128(6) Uani 1 1 d .
H8A H 0.7574 0.3457 0.7950 0.192 Uiso 1 1 calc R
H8B H 0.8519 0.2429 0.8230 0.192 Uiso 1 1 calc R
H8C H 0.7913 0.3260 0.8818 0.192 Uiso 1 1 calc R
C9 C 0.6835(9) 0.0887(12) 0.7620(6) 0.089(4) Uani 1 1 d .
H9A H 0.6334 0.0133 0.7666 0.133 Uiso 1 1 calc R
H9B H 0.7507 0.0518 0.7482 0.133 Uiso 1 1 calc R
H9C H 0.6535 0.1528 0.7236 0.133 Uiso 1 1 calc R
C11 C 0.7045(14) 0.137(2) 1.0099(6) 0.036(3) Uani 1 1 d .
C12 C 0.7218(14) 0.2750(19) 1.0299(8) 0.063(4) Uani 1 1 d .
H12 H 0.6667 0.3408 1.0202 0.076 Uiso 1 1 calc R
C13 C 0.822(2) 0.3139(12) 1.0647(8) 0.066(4) Uani 1 1 d .
H13 H 0.8317 0.4080 1.0771 0.079 Uiso 1 1 calc R
C14 C 0.9086(13) 0.224(2) 1.0828(6) 0.047(3) Uani 1 1 d .
C15 C 0.8860(15) 0.087(2) 1.0636(8) 0.060(3) Uani 1 1 d .
H15 H 0.9391 0.0191 1.0761 0.072 Uiso 1 1 calc R
C16 C 0.7864(19) 0.0446(13) 1.0262(8) 0.051(3) Uani 1 1 d .
H16 H 0.7761 -0.0487 1.0122 0.061 Uiso 1 1 calc R
C17 C 1.0154(12) 0.2719(12) 1.1208(8) 0.055(3) Uani 1 1 d .
C18 C 1.0852(9) 0.3234(14) 1.0603(8) 0.122(5) Uani 1 1 d .
H18A H 1.0512 0.4031 1.0348 0.183 Uiso 1 1 calc R
H18B H 1.0925 0.2499 1.0244 0.183 Uiso 1 1 calc R
H18C H 1.1557 0.3495 1.0838 0.183 Uiso 1 1 calc R
C19 C 1.0075(10) 0.3911(15) 1.1739(8) 0.145(7) Uani 1 1 d .
H19A H 0.9871 0.4744 1.1456 0.217 Uiso 1 1 calc R
H19B H 1.0766 0.4054 1.2029 0.217 Uiso 1 1 calc R
H19C H 0.9539 0.3705 1.2074 0.217 Uiso 1 1 calc R
C20 C 1.0805(11) 0.1565(14) 1.1615(8) 0.147(7) Uani 1 1 d .
H20A H 1.1543 0.1866 1.1731 0.220 Uiso 1 1 calc R
H20B H 1.0785 0.0750 1.1297 0.220 Uiso 1 1 calc R
H20C H 1.0502 0.1341 1.2075 0.220 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'
Zn Zn 0.2839 1.4301 '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
C1 Zn1 N2 127.6(4) . .
C1 Zn1 N1 124.1(4) . 3_657
N2 Zn1 N1 106.4(4) . 3_657
C1 Zn1 N1 121.2(4) . .
N2 Zn1 N1 62.3(4) . .
N1 Zn1 N1 93.9(4) 3_657 .
C1 Zn1 C6 126.9(4) . .
N2 Zn1 C6 30.6(3) . .
N1 Zn1 C6 106.4(3) 3_657 .
N1 Zn1 C6 32.2(3) . .
C1 Zn1 Zn1 141.7(3) . 3_657
N2 Zn1 Zn1 80.2(3) . 3_657
N1 Zn1 Zn1 51.1(3) 3_657 3_657
N1 Zn1 Zn1 42.7(2) . 3_657
C6 Zn1 Zn1 62.1(3) . 3_657
C6 N1 C11 117.9(10) . .
C6 N1 Zn1 114.1(8) . 3_657
C11 N1 Zn1 122.5(10) . 3_657
C6 N1 Zn1 81.8(9) . .
C11 N1 Zn1 123.5(7) . .
Zn1 N1 Zn1 86.1(4) 3_657 .
C6 N2 C3 123.6(10) . .
C6 N2 Zn1 96.6(9) . .
C3 N2 Zn1 139.8(9) . .
C6 N3 C7 128.6(10) . .
C2 C1 Zn1 115.2(7) . .
N2 C3 C4 111.7(9) . .
N2 C3 C5 108.8(11) . .
C4 C3 C5 111.9(10) . .
N2 C6 N1 117.2(13) . .
N2 C6 N3 122.8(14) . .
N1 C6 N3 119.9(13) . .
N2 C6 Zn1 52.8(7) . .
N1 C6 Zn1 65.9(8) . .
N3 C6 Zn1 169.1(7) . .
N3 C7 C9 112.5(11) . .
N3 C7 C8 109.4(10) . .
C9 C7 C8 113.0(11) . .
C16 C11 C12 118.5(12) . .
C16 C11 N1 119.0(18) . .
C12 C11 N1 122.4(17) . .
C11 C12 C13 119.0(11) . .
C12 C13 C14 125.2(11) . .
C15 C14 C13 113.6(11) . .
C15 C14 C17 123.5(18) . .
C13 C14 C17 122.9(18) . .
C14 C15 C16 122.5(11) . .
C11 C16 C15 121.2(11) . .
C19 C17 C14 114.0(11) . .
C19 C17 C20 108.9(12) . .
C14 C17 C20 113.4(11) . .
C19 C17 C18 106.3(11) . .
C14 C17 C18 108.7(10) . .
C20 C17 C18 104.9(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 C1 1.960(9) .
Zn1 N2 2.036(8) .
Zn1 N1 2.040(9) 3_657
Zn1 N1 2.342(10) .
Zn1 C6 2.539(16) .
Zn1 Zn1 3.001(2) 3_657
N1 C6 1.369(13) .
N1 C11 1.438(13) .
N1 Zn1 2.040(9) 3_657
N2 C6 1.302(12) .
N2 C3 1.445(12) .
N3 C6 1.377(13) .
N3 C7 1.459(13) .
C1 C2 1.538(12) .
C3 C4 1.482(12) .
C3 C5 1.521(12) .
C7 C9 1.479(13) .
C7 C8 1.490(13) .
C11 C16 1.356(13) .
C11 C12 1.371(13) .
C12 C13 1.373(14) .
C13 C14 1.389(13) .
C14 C15 1.376(14) .
C14 C17 1.492(14) .
C15 C16 1.396(13) .
C17 C19 1.488(13) .
C17 C20 1.503(14) .
C17 C18 1.534(13) .
