#------------------------------------------------------------------------------
#$Date: 2016-03-21 11:03:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178678 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/89/4078983.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_4078983
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         'C26 H22 N4 O2, 2(C2 H6 O)'
_chemical_formula_sum            'C30 H34 N4 O4'
_chemical_formula_weight         514.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 97.229(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.9343(11)
_cell_length_b                   5.9347(5)
_cell_length_c                   20.2950(18)
_cell_measurement_reflns_used    638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.19
_cell_measurement_theta_min      3.30
_cell_volume                     1426.0(2)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4093
_diffrn_reflns_theta_full        16.44
_diffrn_reflns_theta_max         16.44
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0481
_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)+(0.0717P)²+2.0715P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1370
_reflns_number_gt                613
_reflns_number_total             760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300022u_si_003.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4078983
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O2 O 0.7551(3) 0.2042(8) 0.5902(2) 0.0663(14) Uani 1 1 d .
H2C H 0.8046 0.2860 0.5788 0.099 Uiso 1 1 calc R
O1 O 1.1923(4) 0.1031(9) 0.4940(2) 0.0669(15) Uani 1 1 d .
H1 H 1.2208 0.0199 0.4684 0.100 Uiso 1 1 calc R
N1 N 1.0268(5) 0.6301(13) 0.6641(4) 0.0643(18) Uani 1 1 d .
C6 C 1.0298(6) 0.3944(11) 0.5637(4) 0.0417(19) Uani 1 1 d .
N2 N 0.9165(4) 0.4836(7) 0.5445(2) 0.0451(16) Uani 1 1 d .
H2B H 0.8530 0.4499 0.5492 0.068 Uiso 1 1 d R
C7 C 1.1149(6) 0.5282(10) 0.5288(3) 0.0411(18) Uani 1 1 d .
H7 H 1.1108 0.6862 0.5422 0.049 Uiso 1 1 calc R
C1 C 1.0556(6) 0.4364(19) 0.6374(5) 0.050(3) Uani 1 1 d .
C10 C 1.3878(11) 0.1838(14) 0.5374(4) 0.061(2) Uani 1 1 d .
H10 H 1.4116 0.0451 0.5230 0.073 Uiso 1 1 calc R
C5 C 1.0513(7) 0.6540(15) 0.7305(6) 0.074(2) Uani 1 1 d .
H5 H 1.0318 0.7892 0.7492 0.088 Uiso 1 1 calc R
C2 C 1.1080(7) 0.2692(16) 0.6764(6) 0.068(3) Uani 1 1 d .
H2 H 1.1273 0.1350 0.6570 0.082 Uiso 1 1 calc R
C9 C 1.2743(9) 0.2439(19) 0.5258(3) 0.046(2) Uani 1 1 d .
C12 C 1.4280(11) 0.533(2) 0.5915(3) 0.066(2) Uani 1 1 d .
H12 H 1.4790 0.6323 0.6146 0.079 Uiso 1 1 calc R
C13 C 1.3153(12) 0.5902(13) 0.5785(4) 0.052(2) Uani 1 1 d .
H13 H 1.2925 0.7295 0.5930 0.063 Uiso 1 1 calc R
C4 C 1.1025(7) 0.494(2) 0.7719(4) 0.074(3) Uani 1 1 d .
H4 H 1.1167 0.5183 0.8175 0.089 Uiso 1 1 calc R
C3 C 1.1322(6) 0.2977(18) 0.7438(7) 0.081(3) Uani 1 1 d .
H3 H 1.1684 0.1844 0.7700 0.097 Uiso 1 1 calc R
C11 C 1.4642(7) 0.330(3) 0.5703(4) 0.071(3) Uani 1 1 d .
H11 H 1.5403 0.2920 0.5782 0.085 Uiso 1 1 calc R
C8 C 1.2351(8) 0.4514(19) 0.5451(4) 0.0409(19) Uani 1 1 d .
C14 C 0.7882(8) 0.1264(18) 0.6551(4) 0.146(4) Uani 1 1 d .
H14A H 0.7770 0.2456 0.6863 0.176 Uiso 1 1 calc R
H14B H 0.8681 0.0905 0.6601 0.176 Uiso 1 1 calc R
C15 C 0.7265(9) -0.0684(19) 0.6709(5) 0.168(4) Uani 1 1 d .
H15A H 0.6498 -0.0269 0.6746 0.253 Uiso 1 1 calc R
H15B H 0.7606 -0.1306 0.7123 0.253 Uiso 1 1 calc R
H15C H 0.7276 -0.1786 0.6364 0.253 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
C1 N1 C5 117.5(6) . .
N2 C6 C1 105.7(6) . .
N2 C6 C7 109.6(6) . .
C1 C6 C7 108.0(6) . .
C6 N2 C7 111.0(5) . 3_766
N2 C7 C8 108.6(6) 3_766 .
N2 C7 C6 109.9(6) 3_766 .
C8 C7 C6 114.3(6) . .
N1 C1 C2 120.7(7) . .
N1 C1 C6 121.0(9) . .
C2 C1 C6 118.3(9) . .
C11 C10 C9 119.6(7) . .
N1 C5 C4 124.7(7) . .
C1 C2 C3 120.7(8) . .
O1 C9 C8 115.0(10) . .
O1 C9 C10 122.7(12) . .
C8 C9 C10 122.3(7) . .
C11 C12 C13 119.7(7) . .
C8 C13 C12 123.3(7) . .
C5 C4 C3 117.2(7) . .
C4 C3 C2 119.3(7) . .
C12 C11 C10 119.6(7) . .
C13 C8 C9 115.5(7) . .
C13 C8 C7 120.9(10) . .
C9 C8 C7 123.5(10) . .
O2 C14 C15 112.6(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C14 1.404(8) .
O1 C9 1.383(7) .
N1 C1 1.335(8) .
N1 C5 1.349(9) .
C6 N2 1.460(7) .
C6 C1 1.509(9) .
C6 C7 1.531(8) .
N2 C7 1.489(6) 3_766
C7 N2 1.489(6) 3_766
C7 C8 1.502(8) .
C1 C2 1.370(9) .
C10 C11 1.372(9) .
C10 C9 1.391(8) .
C5 C4 1.359(9) .
C2 C3 1.372(9) .
C9 C8 1.391(8) .
C12 C11 1.366(9) .
C12 C13 1.379(8) .
C13 C8 1.375(8) .
C4 C3 1.366(9) .
C14 C15 1.428(11) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2C N2 0.82 1.97 2.787(6) 175.6 .
O1 H1 O2 0.82 1.83 2.629(6) 163.7 3_756
N2 H2B O2 0.80 2.10 2.787(6) 143.2 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C6 N2 C7 174.6(5) . 3_766
C7 C6 N2 C7 58.5(7) . 3_766
N2 C6 C7 N2 -57.9(6) . 3_766
C1 C6 C7 N2 -172.5(6) . 3_766
N2 C6 C7 C8 179.8(6) . .
C1 C6 C7 C8 65.1(8) . .
C5 N1 C1 C2 0.0(9) . .
C5 N1 C1 C6 179.1(5) . .
N2 C6 C1 N1 -41.2(7) . .
C7 C6 C1 N1 76.0(7) . .
N2 C6 C1 C2 137.9(5) . .
C7 C6 C1 C2 -104.9(6) . .
C1 N1 C5 C4 -0.4(10) . .
N1 C1 C2 C3 -0.2(9) . .
C6 C1 C2 C3 -179.3(6) . .
C11 C10 C9 O1 -178.8(5) . .
C11 C10 C9 C8 1.4(9) . .
C11 C12 C13 C8 0.5(9) . .
N1 C5 C4 C3 0.9(10) . .
C5 C4 C3 C2 -1.0(10) . .
C1 C2 C3 C4 0.7(10) . .
C13 C12 C11 C10 -1.3(10) . .
C9 C10 C11 C12 0.3(9) . .
C12 C13 C8 C9 1.1(8) . .
C12 C13 C8 C7 -176.3(5) . .
O1 C9 C8 C13 178.2(5) . .
C10 C9 C8 C13 -2.0(8) . .
O1 C9 C8 C7 -4.5(8) . .
C10 C9 C8 C7 175.3(5) . .
N2 C7 C8 C13 121.8(6) 3_766 .
C6 C7 C8 C13 -115.2(6) . .
N2 C7 C8 C9 -55.4(7) 3_766 .
C6 C7 C8 C9 67.7(7) . .
