#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:03:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178678 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/89/4078982.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_4078982
loop_
_publ_author_name
'Chen, Zhou'
'Wu, Jian'
'Chen, Yanmei'
'Li, Lei'
'Xia, Yuanzhi'
'Li, Yahong'
'Liu, Wei'
'Lei, Tao'
'Yang, Lijuan'
'Gao, Dandan'
'Li, Wu'
_publ_section_title
;
 Rapid Access to Substituted Piperazines via Ti(NMe2)4-Mediated C--C
 Bond-Making Reactions
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              6005
_journal_paper_doi               10.1021/om300022u
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C16 H31 N5 O Ti'
_chemical_formula_sum            'C16 H31 N5 O Ti'
_chemical_formula_weight         357.36
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.383(4)
_cell_length_b                   15.316(5)
_cell_length_c                   25.274(10)
_cell_measurement_reflns_used    964
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.17
_cell_measurement_theta_min      2.53
_cell_volume                     4019(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.719
_diffrn_measured_fraction_theta_max 0.719
_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  0.1044
_diffrn_reflns_av_sigmaI/netI    0.0968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9267
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_correction_T_min  0.8987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0548
_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)+(0.0426P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                1022
_reflns_number_total             2265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300022u_si_003.cif
_cod_data_source_block           6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
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_cell_volume        4019(2)
_cod_database_code               4078982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
Ti Ti 0.23848(9) 0.07299(7) 0.40102(4) 0.0622(4) Uani 1 1 d .
N2 N 0.2452(5) 0.0833(3) 0.31258(16) 0.0631(14) Uani 1 1 d .
N4 N 0.2679(5) 0.0874(4) 0.47454(18) 0.0824(16) Uani 1 1 d .
N3 N 0.2295(4) -0.0485(3) 0.40022(15) 0.0596(13) Uani 1 1 d .
O1 O 0.3232(4) -0.0375(4) 0.2306(2) 0.119(2) Uani 1 1 d .
N5 N 0.0714(4) 0.1254(3) 0.3983(2) 0.0741(16) Uani 1 1 d .
C6 C 0.1569(5) 0.0406(5) 0.2751(3) 0.078(2) Uani 1 1 d .
H6A H 0.1453 0.0781 0.2446 0.094 Uiso 1 1 calc R
H6B H 0.0736 0.0332 0.2919 0.094 Uiso 1 1 calc R
N1 N 0.4103(5) 0.1371(3) 0.3827(3) 0.0648(16) Uani 1 1 d .
C4 C 0.5135(7) 0.1684(4) 0.4097(3) 0.083(2) Uani 1 1 d .
H4 H 0.5256 0.1633 0.4460 0.100 Uiso 1 1 calc R
C1 C 0.4310(6) 0.1598(4) 0.3309(3) 0.068(2) Uani 1 1 d .
C16 C 0.3492(6) -0.0959(4) 0.3934(2) 0.105(2) Uani 1 1 d .
H16A H 0.3634 -0.1328 0.4235 0.158 Uiso 1 1 calc R
H16B H 0.4191 -0.0552 0.3902 0.158 Uiso 1 1 calc R
H16C H 0.3442 -0.1310 0.3620 0.158 Uiso 1 1 calc R
C5 C 0.3385(7) 0.1277(4) 0.2944(2) 0.073(2) Uani 1 1 d .
H5 H 0.3460 0.1389 0.2583 0.088 Uiso 1 1 calc R
C15 C 0.1240(5) -0.1080(4) 0.4088(2) 0.094(2) Uani 1 1 d .
H15A H 0.1190 -0.1483 0.3798 0.140 Uiso 1 1 calc R
H15B H 0.0450 -0.0758 0.4112 0.140 Uiso 1 1 calc R
H15C H 0.1378 -0.1397 0.4411 0.140 Uiso 1 1 calc R
C7 C 0.2055(7) -0.0472(5) 0.2570(3) 0.088(2) Uani 1 1 d .
H7 H 0.2171 -0.0854 0.2877 0.106 Uiso 1 1 calc R
C14 C 0.0179(5) 0.1835(4) 0.3596(2) 0.092(2) Uani 1 1 d .
H14A H -0.0089 0.2366 0.3765 0.139 Uiso 1 1 calc R
H14B H -0.0549 0.1563 0.3430 0.139 Uiso 1 1 calc R
H14C H 0.0819 0.1965 0.3333 0.139 Uiso 1 1 calc R
C2 C 0.5449(7) 0.2042(4) 0.3259(3) 0.088(2) Uani 1 1 d .
H2 H 0.5796 0.2269 0.2949 0.106 Uiso 1 1 calc R
C12 C 0.3056(5) 0.0253(5) 0.5140(3) 0.114(3) Uani 1 1 d .
H12A H 0.3924 0.0370 0.5249 0.172 Uiso 1 1 calc R
H12B H 0.3006 -0.0326 0.4995 0.172 Uiso 1 1 calc R
H12C H 0.2491 0.0298 0.5439 0.172 Uiso 1 1 calc R
C9 C 0.1772(7) -0.0809(6) 0.1680(3) 0.141(3) Uani 1 1 d U
H9A H 0.1320 -0.0381 0.1467 0.169 Uiso 1 1 calc R
H9B H 0.1776 -0.1360 0.1491 0.169 Uiso 1 1 calc R
C3 C 0.5974(7) 0.2087(5) 0.3756(4) 0.093(3) Uani 1 1 d .
H3 H 0.6757 0.2343 0.3846 0.111 Uiso 1 1 calc R
C10 C 0.3071(6) -0.0524(6) 0.1778(4) 0.129(3) Uani 1 1 d .
H10A H 0.3672 -0.0968 0.1660 0.155 Uiso 1 1 calc R
H10B H 0.3242 0.0008 0.1581 0.155 Uiso 1 1 calc R
C11 C 0.2625(7) 0.1747(5) 0.4988(3) 0.157(3) Uani 1 1 d .
H11A H 0.2080 0.1730 0.5294 0.236 Uiso 1 1 calc R
H11B H 0.2285 0.2158 0.4737 0.236 Uiso 1 1 calc R
H11C H 0.3477 0.1924 0.5091 0.236 Uiso 1 1 calc R
C8 C 0.1156(6) -0.0908(5) 0.2175(3) 0.122(3) Uani 1 1 d U
H8A H 0.1040 -0.1520 0.2259 0.147 Uiso 1 1 calc R
H8B H 0.0320 -0.0624 0.2173 0.147 Uiso 1 1 calc R
C13 C -0.0201(7) 0.1159(5) 0.4413(3) 0.139(3) Uani 1 1 d .
H13A H -0.0266 0.1700 0.4603 0.208 Uiso 1 1 calc R
H13B H 0.0086 0.0708 0.4649 0.208 Uiso 1 1 calc R
H13C H -0.1030 0.1006 0.4272 0.208 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'
Ti Ti 0.2776 0.4457 '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
N3 Ti N4 97.8(2)
N3 Ti N5 111.9(2)
N4 Ti N5 97.6(2)
N3 Ti N1 120.67(19)
N4 Ti N1 91.4(2)
N5 Ti N1 124.7(2)
N3 Ti N2 93.50(18)
N4 Ti N2 164.6(2)
N5 Ti N2 87.9(2)
N1 Ti N2 73.7(2)
C5 N2 C6 118.7(5)
C5 N2 Ti 115.0(4)
C6 N2 Ti 126.2(4)
C12 N4 C11 108.9(5)
C12 N4 Ti 130.4(5)
C11 N4 Ti 120.5(5)
C15 N3 C16 110.6(5)
C15 N3 Ti 131.9(4)
C16 N3 Ti 117.3(4)
C10 O1 C7 109.9(5)
C14 N5 C13 108.7(5)
C14 N5 Ti 129.4(4)
C13 N5 Ti 121.7(5)
N2 C6 C7 112.5(5)
C4 N1 C1 105.5(6)
C4 N1 Ti 136.7(6)
C1 N1 Ti 117.7(5)
N1 C4 C3 110.1(7)
N1 C1 C2 110.5(6)
N1 C1 C5 115.3(7)
C2 C1 C5 134.0(9)
N2 C5 C1 117.7(6)
O1 C7 C6 110.0(6)
O1 C7 C8 105.7(5)
C6 C7 C8 112.7(6)
C1 C2 C3 106.4(7)
C8 C9 C10 107.8(7)
C4 C3 C2 107.5(7)
O1 C10 C9 109.5(6)
C9 C8 C7 104.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ti N3 1.862(4)
Ti N4 1.896(5)
Ti N5 1.913(5)
Ti N1 2.088(5)
Ti N2 2.242(4)
N2 C5 1.270(6)
N2 C6 1.470(7)
N4 C12 1.433(7)
N4 C11 1.472(7)
N3 C15 1.442(6)
N3 C16 1.449(6)
O1 C10 1.366(7)
O1 C7 1.400(7)
N5 C14 1.435(6)
N5 C13 1.450(6)
C6 C7 1.508(8)
N1 C4 1.359(6)
N1 C1 1.369(7)
C4 C3 1.372(8)
C1 C2 1.370(7)
C1 C5 1.420(7)
C7 C8 1.522(7)
C2 C3 1.372(8)
C9 C8 1.412(8)
C9 C10 1.438(8)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N3 Ti N2 C5 -126.9(4)
N4 Ti N2 C5 10.0(10)
N5 Ti N2 C5 121.3(5)
N1 Ti N2 C5 -5.9(4)
N3 Ti N2 C6 50.0(5)
N4 Ti N2 C6 -173.1(8)
N5 Ti N2 C6 -61.8(5)
N1 Ti N2 C6 171.0(5)
N3 Ti N4 C12 14.6(5)
N5 Ti N4 C12 128.1(5)
N1 Ti N4 C12 -106.6(5)
N2 Ti N4 C12 -121.9(8)
N3 Ti N4 C11 -170.3(5)
N5 Ti N4 C11 -56.8(5)
N1 Ti N4 C11 68.5(5)
N2 Ti N4 C11 53.3(10)
N4 Ti N3 C15 86.8(5)
N5 Ti N3 C15 -14.6(5)
N1 Ti N3 C15 -176.8(5)
N2 Ti N3 C15 -103.8(5)
N4 Ti N3 C16 -88.3(4)
N5 Ti N3 C16 170.2(4)
N1 Ti N3 C16 8.0(5)
N2 Ti N3 C16 81.1(4)
N3 Ti N5 C14 -119.8(5)
N4 Ti N5 C14 138.7(6)
N1 Ti N5 C14 41.6(6)
N2 Ti N5 C14 -26.8(6)
N3 Ti N5 C13 66.0(5)
N4 Ti N5 C13 -35.5(5)
N1 Ti N5 C13 -132.6(5)
N2 Ti N5 C13 158.9(5)
C5 N2 C6 C7 84.9(7)
Ti N2 C6 C7 -91.9(6)
N3 Ti N1 C4 -92.5(6)
N4 Ti N1 C4 7.4(6)
N5 Ti N1 C4 107.7(6)
N2 Ti N1 C4 -176.7(6)
N3 Ti N1 C1 91.0(4)
N4 Ti N1 C1 -169.1(4)
N5 Ti N1 C1 -68.9(5)
N2 Ti N1 C1 6.7(4)
C1 N1 C4 C3 -0.7(7)
Ti N1 C4 C3 -177.5(5)
C4 N1 C1 C2 0.0(7)
Ti N1 C1 C2 177.5(4)
C4 N1 C1 C5 175.5(5)
Ti N1 C1 C5 -6.9(7)
C6 N2 C5 C1 -172.8(5)
Ti N2 C5 C1 4.3(7)
N1 C1 C5 N2 1.4(8)
C2 C1 C5 N2 175.6(7)
C10 O1 C7 C6 -109.1(7)
C10 O1 C7 C8 12.8(8)
N2 C6 C7 O1 -61.3(7)
N2 C6 C7 C8 -178.9(5)
N1 C1 C2 C3 0.7(8)
C5 C1 C2 C3 -173.7(7)
N1 C4 C3 C2 1.1(8)
C1 C2 C3 C4 -1.1(8)
C7 O1 C10 C9 -5.3(9)
C8 C9 C10 O1 -5.1(10)
C10 C9 C8 C7 12.4(10)
O1 C7 C8 C9 -15.4(9)
C6 C7 C8 C9 104.7(8)
