#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/01/57/7015730.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_7015730
loop_
_publ_author_name
'Godau, Tom'
'Bleifuß, Sascha M'
'Müller, Astrid L'
'Roth, Thomas'
'Hoffmann, Susanne'
'Heinemann, Frank W.'
'Burzlaff, Nicolai'
_publ_section_title
;
 Cu(i) catalysed cyclopropanation with enantiopure scorpionate type
 ligands derived from (+)-camphor or (-)-menthone.
;
_journal_issue                   24
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6547
_journal_page_last               6554
_journal_paper_doi               10.1039/c1dt10032g
_journal_volume                  40
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C27 H36 N6'
_chemical_formula_sum            'C27 H36 N6'
_chemical_formula_weight         444.62
_chemical_name_systematic
;
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-11-22T22:48:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 133.701(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.4805(12)
_cell_length_b                   7.7565(5)
_cell_length_c                   17.8684(7)
_cell_measurement_reflns_used    136
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      6
_cell_measurement_wavelength     0.71073
_cell_volume                     2553.1(3)
_computing_cell_refinement       'EVALCCD (Duisenberg, 2003)'
_computing_data_collection       'COLLECT (Bruker-Nonius, 2002)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
φ- and ω-rotations with 2.00 ° and 100 sec per frame
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39319
_diffrn_reflns_theta_full        28.52
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         2.85
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.952022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_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     298
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0699P)²+0.6097P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                2971
_reflns_number_total             3470
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10032g.txt
_cod_data_source_block           tgbu03
_cod_original_cell_volume        2553.1(2)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7015730
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'
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
C1 C 0.08535(10) 0.6440(2) 0.15127(15) 0.0176(4) Uani 1 1 d . . .
H1 H 0.0698 0.6818 0.0861 0.021 Uiso 1 1 calc R . .
C2 C 0.07353(10) 0.4524(3) 0.14540(16) 0.0209(4) Uani 1 1 d . . .
C3 C 0.05574(14) 0.1973(3) 0.1677(2) 0.0406(6) Uani 1 1 d . . .
H3 H 0.0422 0.1061 0.1852 0.049 Uiso 1 1 calc R . .
C4 C 0.08445(14) 0.1792(3) 0.1274(2) 0.0400(6) Uani 1 1 d . . .
H4 H 0.0945 0.0764 0.1126 0.048 Uiso 1 1 calc R . .
C5 C 0.12979(14) 0.3904(4) 0.0744(2) 0.0358(5) Uani 1 1 d . . .
H5A H 0.0935 0.4359 0.0055 0.054 Uiso 1 1 calc R . .
H5B H 0.1515 0.29 0.0737 0.054 Uiso 1 1 calc R . .
H5C H 0.1665 0.4761 0.1191 0.054 Uiso 1 1 calc R . .
C11 C 0.21329(11) 0.5828(3) 0.32225(16) 0.0238(4) Uani 1 1 d . . .
H11 H 0.2065 0.4767 0.3388 0.029 Uiso 1 1 calc R . .
C12 C 0.27625(11) 0.6754(3) 0.37996(15) 0.0230(4) Uani 1 1 d . . .
C13 C 0.25825(10) 0.8232(3) 0.32166(15) 0.0213(4) Uani 1 1 d . . .
C14 C 0.32505(12) 0.9321(3) 0.37810(18) 0.0338(5) Uani 1 1 d . . .
C15 C 0.37374(14) 0.8234(5) 0.3721(2) 0.0529(8) Uani 1 1 d . . .
H15A H 0.347 0.7916 0.3011 0.064 Uiso 1 1 calc R . .
H15B H 0.4166 0.888 0.3997 0.064 Uiso 1 1 calc R . .
C16 C 0.39493(14) 0.6622(5) 0.4383(3) 0.0529(8) Uani 1 1 d . . .
H16A H 0.4471 0.6552 0.4962 0.064 Uiso 1 1 calc R . .
H16B H 0.378 0.5579 0.3972 0.064 Uiso 1 1 calc R . .
C17 C 0.35639(12) 0.6892(4) 0.47592(18) 0.0340(5) Uani 1 1 d . . .
H17 H 0.3741 0.6187 0.5351 0.041 Uiso 1 1 calc R . .
C18 C 0.36225(13) 0.8883(4) 0.49219(18) 0.0334(5) Uani 1 1 d . . .
C19 C 0.32023(16) 0.9541(5) 0.5181(2) 0.0531(8) Uani 1 1 d . . .
H19A H 0.271 0.9138 0.467 0.08 Uiso 1 1 calc R . .
H19B H 0.3206 1.0779 0.5186 0.08 Uiso 1 1 calc R . .
H19C H 0.3425 0.9123 0.5851 0.08 Uiso 1 1 calc R . .
C20 C 0.44032(15) 0.9558(5) 0.5755(2) 0.0526(8) Uani 1 1 d . . .
H20A H 0.4683 0.9149 0.5614 0.079 Uiso 1 1 calc R . .
H20B H 0.4616 0.9152 0.6422 0.079 Uiso 1 1 calc R . .
H20C H 0.4399 1.0796 0.575 0.079 Uiso 1 1 calc R . .
C21 C 0.31333(18) 1.1182(4) 0.3458(3) 0.0662(11) Uani 1 1 d . . .
H21A H 0.3594 1.1751 0.3869 0.099 Uiso 1 1 calc R . .
H21B H 0.2849 1.1737 0.356 0.099 Uiso 1 1 calc R . .
H21C H 0.2882 1.1246 0.2741 0.099 Uiso 1 1 calc R . .
C31 C 0.05897(10) 0.7616(3) 0.25510(14) 0.0211(4) Uani 1 1 d . . .
H31 H 0.1037 0.745 0.3222 0.025 Uiso 1 1 calc R . .
C32 C -0.00412(10) 0.8150(3) 0.22606(15) 0.0207(4) Uani 1 1 d . . .
C33 C -0.05515(10) 0.8166(3) 0.11758(15) 0.0197(4) Uani 1 1 d . . .
C34 C -0.12689(11) 0.8787(3) 0.07740(16) 0.0247(4) Uani 1 1 d . . .
C35 C -0.11339(14) 1.0730(3) 0.1084(2) 0.0355(5) Uani 1 1 d . . .
H35A H -0.1582 1.1294 0.0789 0.043 Uiso 1 1 calc R . .
H35B H -0.0935 1.132 0.0848 0.043 Uiso 1 1 calc R . .
C36 C -0.05788(15) 1.0721(4) 0.2290(2) 0.0394(6) Uani 1 1 d . . .
H36A H -0.0135 1.1318 0.2591 0.047 Uiso 1 1 calc R . .
H36B H -0.0783 1.1255 0.2533 0.047 Uiso 1 1 calc R . .
C37 C -0.04373(12) 0.8773(3) 0.25582(17) 0.0309(5) Uani 1 1 d . . .
H37 H -0.0217 0.8466 0.3257 0.037 Uiso 1 1 calc R . .
C38 C -0.12057(12) 0.7971(4) 0.16420(19) 0.0330(6) Uani 1 1 d . . .
C39 C -0.12091(16) 0.5998(4) 0.1638(3) 0.0504(8) Uani 1 1 d . . .
H39A H -0.0839 0.5582 0.167 0.076 Uiso 1 1 calc R . .
H39B H -0.1674 0.559 0.1015 0.076 Uiso 1 1 calc R . .
H39C H -0.1116 0.5583 0.2227 0.076 Uiso 1 1 calc R . .
C40 C -0.18000(14) 0.8623(5) 0.1595(2) 0.0521(8) Uani 1 1 d . . .
H40A H -0.18 0.9861 0.16 0.078 Uiso 1 1 calc R . .
H40B H -0.1705 0.82 0.2184 0.078 Uiso 1 1 calc R . .
H40C H -0.2265 0.8215 0.0971 0.078 Uiso 1 1 calc R . .
C41 C -0.19387(11) 0.8392(5) -0.03453(18) 0.0414(7) Uani 1 1 d . . .
H41A H -0.2359 0.8851 -0.0513 0.062 Uiso 1 1 calc R . .
H41B H -0.199 0.7166 -0.0448 0.062 Uiso 1 1 calc R . .
H41C H -0.1892 0.8908 -0.0785 0.062 Uiso 1 1 calc R . .
N1 N 0.04882(10) 0.3699(2) 0.17990(16) 0.0303(4) Uani 1 1 d . . .
N2 N 0.09605(10) 0.3436(2) 0.11258(14) 0.0269(4) Uani 1 1 d . . .
N11 N 0.18947(9) 0.8300(2) 0.23281(13) 0.0221(4) Uani 1 1 d . . .
N12 N 0.16214(8) 0.6793(2) 0.23464(12) 0.0179(3) Uani 1 1 d . . .
N31 N -0.02864(8) 0.7692(2) 0.07845(12) 0.0203(3) Uani 1 1 d . . .
N32 N 0.04295(8) 0.7375(2) 0.16538(12) 0.0175(3) 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 0 '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'
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
N12 C1 N32 111.31(15) . . ?
N12 C1 C2 108.76(16) . . ?
N32 C1 C2 111.46(16) . . ?
N12 C1 H1 108.4 . . ?
N32 C1 H1 108.4 . . ?
C2 C1 H1 108.4 . . ?
N1 C2 N2 112.45(19) . . ?
N1 C2 C1 125.92(19) . . ?
N2 C2 C1 121.25(18) . . ?
C4 C3 N1 111.2(2) . . ?
C4 C3 H3 124.4 . . ?
N1 C3 H3 124.4 . . ?
C3 C4 N2 106.0(2) . . ?
C3 C4 H4 127 . . ?
N2 C4 H4 127 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C11 N12 105.55(18) . . ?
C12 C11 H11 127.2 . . ?
N12 C11 H11 127.2 . . ?
C11 C12 C13 105.03(17) . . ?
C11 C12 C17 148.8(2) . . ?
C13 C12 C17 106.14(19) . . ?
N11 C13 C12 114.10(18) . . ?
N11 C13 C14 136.9(2) . . ?
C12 C13 C14 108.98(18) . . ?
C13 C14 C21 116.7(2) . . ?
C13 C14 C15 103.6(2) . . ?
C21 C14 C15 116.6(3) . . ?
C13 C14 C18 97.85(18) . . ?
C21 C14 C18 118.9(2) . . ?
C15 C14 C18 100.1(2) . . ?
C16 C15 C14 105.0(2) . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15B 110.7 . . ?
C14 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C15 C16 C17 103.5(2) . . ?
C15 C16 H16A 111.1 . . ?
C17 C16 H16A 111.1 . . ?
C15 C16 H16B 111.1 . . ?
C17 C16 H16B 111.1 . . ?
H16A C16 H16B 109 . . ?
C12 C17 C16 105.3(2) . . ?
C12 C17 C18 99.3(2) . . ?
C16 C17 C18 102.0(2) . . ?
C12 C17 H17 116 . . ?
C16 C17 H17 116 . . ?
C18 C17 H17 116 . . ?
C19 C18 C20 107.7(2) . . ?
C19 C18 C17 113.1(2) . . ?
C20 C18 C17 114.3(2) . . ?
C19 C18 C14 113.6(2) . . ?
C20 C18 C14 113.5(2) . . ?
C17 C18 C14 94.45(19) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N32 C31 C32 106.02(16) . . ?
N32 C31 H31 127 . . ?
C32 C31 H31 127 . . ?
C31 C32 C33 104.55(17) . . ?
C31 C32 C37 149.31(19) . . ?
C33 C32 C37 106.10(16) . . ?
N31 C33 C32 113.95(17) . . ?
N31 C33 C34 137.24(18) . . ?
C32 C33 C34 108.79(16) . . ?
C33 C34 C41 116.96(18) . . ?
C33 C34 C35 104.04(18) . . ?
C41 C34 C35 115.8(2) . . ?
C33 C34 C38 97.86(16) . . ?
C41 C34 C38 118.3(2) . . ?
C35 C34 C38 101.01(18) . . ?
C34 C35 C36 104.68(19) . . ?
C34 C35 H35A 110.8 . . ?
C36 C35 H35A 110.8 . . ?
C34 C35 H35B 110.8 . . ?
C36 C35 H35B 110.8 . . ?
H35A C35 H35B 108.9 . . ?
C37 C36 C35 103.1(2) . . ?
C37 C36 H36A 111.1 . . ?
C35 C36 H36A 111.1 . . ?
C37 C36 H36B 111.1 . . ?
C35 C36 H36B 111.1 . . ?
H36A C36 H36B 109.1 . . ?
C32 C37 C36 105.85(19) . . ?
C32 C37 C38 99.28(17) . . ?
C36 C37 C38 101.96(19) . . ?
C32 C37 H37 115.9 . . ?
C36 C37 H37 115.9 . . ?
C38 C37 H37 115.9 . . ?
C39 C38 C40 109.0(2) . . ?
C39 C38 C37 113.5(2) . . ?
C40 C38 C37 113.4(2) . . ?
C39 C38 C34 113.6(2) . . ?
C40 C38 C34 112.7(2) . . ?
C37 C38 C34 94.17(17) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C34 C41 H41A 109.5 . . ?
C34 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C34 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C2 N1 C3 104.0(2) . . ?
C2 N2 C4 106.34(19) . . ?
C2 N2 C5 127.20(19) . . ?
C4 N2 C5 126.4(2) . . ?
C13 N11 N12 102.14(16) . . ?
N11 N12 C11 113.18(15) . . ?
N11 N12 C1 118.94(15) . . ?
C11 N12 C1 127.78(17) . . ?
C33 N31 N32 102.55(15) . . ?
C31 N32 N31 112.91(15) . . ?
C31 N32 C1 127.83(16) . . ?
N31 N32 C1 117.17(15) . . ?
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
C1 N12 1.447(2) . ?
C1 N32 1.461(2) . ?
C1 C2 1.505(3) . ?
C1 H1 0.98 . ?
C2 N1 1.312(3) . ?
C2 N2 1.361(3) . ?
C3 C4 1.342(4) . ?
C3 N1 1.387(3) . ?
C3 H3 0.93 . ?
C4 N2 1.375(3) . ?
C4 H4 0.93 . ?
C5 N2 1.465(3) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C11 C12 1.366(3) . ?
C11 N12 1.375(3) . ?
C11 H11 0.93 . ?
C12 C13 1.396(3) . ?
C12 C17 1.511(3) . ?
C13 N11 1.323(3) . ?
C13 C14 1.502(3) . ?
C14 C21 1.506(4) . ?
C14 C15 1.564(4) . ?
C14 C18 1.581(3) . ?
C15 C16 1.541(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.541(4) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 C18 1.559(4) . ?
C17 H17 0.98 . ?
C18 C19 1.519(4) . ?
C18 C20 1.535(3) . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C21 H21A 0.96 . ?
C21 H21B 0.96 . ?
C21 H21C 0.96 . ?
C31 N32 1.367(3) . ?
C31 C32 1.368(3) . ?
C31 H31 0.93 . ?
C32 C33 1.402(3) . ?
C32 C37 1.509(3) . ?
C33 N31 1.316(3) . ?
C33 C34 1.509(3) . ?
C34 C41 1.513(3) . ?
C34 C35 1.559(3) . ?
C34 C38 1.577(3) . ?
C35 C36 1.560(4) . ?
C35 H35A 0.97 . ?
C35 H35B 0.97 . ?
C36 C37 1.550(4) . ?
C36 H36A 0.97 . ?
C36 H36B 0.97 . ?
C37 C38 1.572(3) . ?
C37 H37 0.98 . ?
C38 C39 1.531(4) . ?
C38 C40 1.543(3) . ?
C39 H39A 0.96 . ?
C39 H39B 0.96 . ?
C39 H39C 0.96 . ?
C40 H40A 0.96 . ?
C40 H40B 0.96 . ?
C40 H40C 0.96 . ?
C41 H41A 0.96 . ?
C41 H41B 0.96 . ?
C41 H41C 0.96 . ?
N11 N12 1.373(2) . ?
N31 N32 1.373(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652817
