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#$Date: 2016-03-21 09:25:51 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178623 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/34/4073433.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_4073433
loop_
_publ_author_name
'Bach, Marc A.'
'Beweries, Torsten'
'Burlakov, Vladimir V.'
'Arndt, Perdita'
'Baumann, Wolfgang'
'Spannenberg, Anke'
'Rosenthal, Uwe'
_publ_section_title
;
 Migratory Insertion of an Isocyanide into 1-Zirconacyclopent-3-ynes
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              4592
_journal_paper_doi               10.1021/om700324k
_journal_volume                  26
_journal_year                    2007
_chemical_formula_sum            'C15 H28 N2 O'
_chemical_formula_weight         252.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 109.70(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.816(3)
_cell_length_b                   10.573(2)
_cell_length_c                   10.120(2)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    200(2)
_cell_volume                     1593.2(6)
_computing_data_collection       STOE-X-AREA
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE-IPDS II'
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10325
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.003(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1491
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0633
_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)+(0.0872P)²+0.4608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                1162
_reflns_number_total             1491
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om700324k_1.cif
_cod_data_source_block           ks483m
_cod_original_cell_volume        1593.3(6)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4073433
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C4 C 0.19613(14) -0.0354(3) 0.0608(3) 0.0271(9) Uani 0.50 1 d PD
C5 C 0.1833(7) -0.1619(16) 0.1194(14) 0.033(2) Uani 0.50 1 d P
H5A H 0.1911 -0.2293 0.0579 0.050 Uiso 0.50 1 calc PR
H5B H 0.1227 -0.1667 0.1248 0.050 Uiso 0.50 1 calc PR
H5C H 0.2277 -0.1722 0.2134 0.050 Uiso 0.50 1 calc PR
O1 O 0.17752(14) 0.0533(2) 0.1539(2) 0.0318(6) Uani 0.50 1 d P
C13 C 0.1803(10) 0.1834(17) 0.1162(17) 0.046(3) Uani 0.50 1 d P
H13A H 0.1659 0.2372 0.1846 0.069 Uiso 0.50 1 calc PR
H13B H 0.1364 0.1980 0.0226 0.069 Uiso 0.50 1 calc PR
H13C H 0.2406 0.2041 0.1156 0.069 Uiso 0.50 1 calc PR
N1 N 0.36371(12) 0.0000 0.04991(18) 0.0295(5) Uani 1 2 d S
N2 N 0.24534(14) 0.0000 -0.2460(2) 0.0365(6) Uani 1 2 d S
HN2 H 0.299(2) 0.0000 -0.223(3) 0.036(7) Uiso 1 2 d S
C1 C 0.27917(15) 0.0000 0.0121(2) 0.0342(6) Uani 1 2 d SD
C2 C 0.21752(15) 0.0000 -0.1332(2) 0.0304(6) Uani 1 2 d S
C3 C 0.14204(16) 0.0000 -0.0975(2) 0.0405(7) Uani 1 2 d SD
C6 C 0.04277(17) 0.0000 -0.1638(3) 0.0500(8) Uani 1 2 d S
H6A H 0.0150 0.0000 -0.0907 0.075 Uiso 1 2 calc SR
H6B H 0.0239 -0.0757 -0.2223 0.075 Uiso 0.50 1 calc PR
H6C H 0.0239 0.0757 -0.2223 0.075 Uiso 0.50 1 calc PR
C7 C 0.19155(15) 0.0000 -0.3956(2) 0.0346(6) Uani 1 2 d S
C8 C 0.13419(15) 0.1181(2) -0.4324(2) 0.0526(6) Uani 1 1 d .
H8A H 0.0914 0.1182 -0.3813 0.079 Uiso 1 1 calc R
H8B H 0.1013 0.1196 -0.5336 0.079 Uiso 1 1 calc R
H8C H 0.1727 0.1930 -0.4062 0.079 Uiso 1 1 calc R
C9 C 0.2582(2) 0.0000 -0.4744(3) 0.0649(10) Uani 1 2 d S
H9A H 0.2951 0.0766 -0.4507 0.097 Uiso 0.50 1 calc PR
H9B H 0.2255 -0.0019 -0.5756 0.097 Uiso 1 2 calc SR
H9C H 0.2969 -0.0747 -0.4476 0.097 Uiso 0.50 1 calc PR
C10 C 0.42733(15) 0.0000 0.1952(2) 0.0342(6) Uani 1 2 d S
C11 C 0.3848(2) 0.0000 0.3078(3) 0.0795(13) Uani 1 2 d S
H11A H 0.3478 -0.0760 0.2986 0.119 Uiso 0.50 1 calc PR
H11B H 0.3470 0.0753 0.2977 0.119 Uiso 0.50 1 calc PR
H11C H 0.4318 0.0007 0.4003 0.119 Uiso 1 2 calc SR
C12 C 0.48474(18) 0.1162(2) 0.2084(2) 0.0755(9) Uani 1 1 d .
H12A H 0.4477 0.1920 0.2005 0.113 Uiso 1 1 calc R
H12B H 0.5110 0.1164 0.1334 0.113 Uiso 1 1 calc R
H12C H 0.5329 0.1158 0.2998 0.113 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C4 C4 O1 99.99(19) 6 6
C4 C4 O1 48.98(15) 6 .
O1 C4 O1 51.0(3) 6 .
C4 C4 C5 152.8(5) 6 .
O1 C4 C5 52.8(5) 6 .
O1 C4 C5 103.8(5) . .
C4 C4 C3 76.36(10) 6 .
O1 C4 C3 134.5(2) 6 .
O1 C4 C3 110.54(19) . .
C5 C4 C3 120.6(5) . .
C4 C4 C1 76.44(10) 6 .
O1 C4 C1 142.7(2) 6 .
O1 C4 C1 115.1(2) . .
C5 C4 C1 124.4(4) . .
C3 C4 C1 81.52(17) . .
C4 C4 C13 156.3(5) 6 6
O1 C4 C13 56.4(5) 6 6
O1 C4 C13 107.4(6) . 6
C5 C4 C13 3.9(10) . 6
C3 C4 C13 117.3(5) . 6
C1 C4 C13 122.9(5) . 6
C4 O1 O1 80.01(19) 6 6
C4 O1 C5 81.2(7) 6 6
O1 O1 C5 161.2(6) 6 6
C4 O1 C4 31.0(2) 6 .
O1 O1 C4 48.98(15) 6 .
C5 O1 C4 112.3(7) 6 .
C4 O1 C13 84.0(7) 6 .
O1 O1 C13 163.8(7) 6 .
C5 O1 C13 3.3(12) 6 .
C4 O1 C13 115.0(7) . .
C1 N1 C10 126.85(18) . .
C2 N2 C7 129.1(2) . .
N1 C1 C2 125.72(19) . .
N1 C1 C4 143.7(2) . .
C2 C1 C4 88.35(16) . .
N1 C1 C4 143.7(2) . 6
C2 C1 C4 88.35(16) . 6
C4 C1 C4 27.1(2) . 6
N2 C2 C3 142.0(2) . .
N2 C2 C1 123.4(2) . .
C3 C2 C1 94.63(18) . .
C2 C3 C6 140.3(2) . .
C2 C3 C4 92.59(17) . 6
C6 C3 C4 125.8(2) . 6
C2 C3 C4 92.59(17) . .
C6 C3 C4 125.8(2) . .
C4 C3 C4 27.3(2) 6 .
N2 C7 C8 110.21(12) . .
N2 C7 C8 110.21(12) . 6
C8 C7 C8 111.1(2) . 6
N2 C7 C9 106.1(2) . .
C8 C7 C9 109.53(13) . .
C8 C7 C9 109.53(13) 6 .
N1 C10 C11 115.2(2) . .
N1 C10 C12 106.05(13) . 6
C11 C10 C12 110.04(15) . 6
N1 C10 C12 106.04(13) . .
C11 C10 C12 110.04(15) . .
C12 C10 C12 109.3(3) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C4 0.748(5) 6
C4 O1 1.095(3) 6
C4 O1 1.429(3) .
C4 C5 1.505(16) .
C4 C3 1.586(3) .
C4 C1 1.595(3) .
C4 C13 1.710(19) 6
O1 C4 1.095(3) 6
O1 O1 1.128(5) 6
O1 C5 1.213(16) 6
O1 C13 1.432(17) .
N1 C1 1.261(3) .
N1 C10 1.475(3) .
N2 C2 1.356(3) .
N2 C7 1.465(3) .
C1 C2 1.465(3) .
C1 C4 1.595(3) 6
C2 C3 1.359(3) .
C3 C6 1.485(3) .
C3 C4 1.586(3) 6
C7 C8 1.514(2) .
C7 C8 1.514(2) 6
C7 C9 1.521(3) .
C10 C11 1.506(4) .
C10 C12 1.507(3) 6
C10 C12 1.507(3) .
