#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:46:54 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180235 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/21/7112166.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_7112166
loop_
_publ_author_name
'Lenard Hussein'
'Nibadita Purkait'
'Mustafa Biyikal'
'Eugenia Tausch'
'Peter W. Roesky'
'Siegfried Blechert'
_publ_section_title
;
 Highly enantioselective hydroamination to six-membered rings by
 heterobimetallic catalysts
;
_journal_name_full               Chem.Commun.
_journal_page_first              3862
_journal_paper_doi               10.1039/C3CC48874H
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H38 Cu N4 O2, C H2 Cl2'
_chemical_formula_sum            'C37 H40 Cl2 Cu N4 O2'
_chemical_formula_weight         707.17
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_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_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.159(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   30.212(2)
_cell_length_b                   7.0191(6)
_cell_length_c                   16.0347(15)
_cell_measurement_reflns_used    1946
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32.5287
_cell_measurement_theta_min      3.2334
_cell_volume                     3400.3(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10978
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.9436
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.019(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0611
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1114
_reflns_number_gt                4928
_reflns_number_total             5886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc48874h2.cif
_cod_data_source_block           Cu2
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7112166
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
Cu1 Cu 0.257410(16) 0.40470(7) 0.53080(4) 0.01609(15) Uani 1 1 d .
O1 O 0.31465(9) 0.3867(6) 0.5803(2) 0.0187(8) Uani 1 1 d .
O2 O 0.23168(9) 0.4128(6) 0.64004(19) 0.0194(7) Uani 1 1 d .
N1 N 0.28075(12) 0.4445(5) 0.4182(3) 0.0189(11) Uani 1 1 d .
N2 N 0.20044(12) 0.3854(7) 0.4747(3) 0.0214(10) Uani 1 1 d .
N3 N 0.38479(11) 0.3928(8) 0.6805(2) 0.0225(9) Uani 1 1 d .
H3 H 0.3593 0.4263 0.7025 0.027 Uiso 1 1 calc R
N4 N 0.21212(12) 0.4301(7) 0.7994(3) 0.0242(10) Uani 1 1 d .
H4 H 0.2372 0.3835 0.7806 0.029 Uiso 1 1 calc R
C1 C 0.24444(15) 0.4649(6) 0.3559(3) 0.0189(12) Uani 1 1 d .
H1 H 0.2344 0.6006 0.3570 0.023 Uiso 1 1 calc R
C2 C 0.25753(14) 0.4179(10) 0.2660(3) 0.0248(11) Uani 1 1 d .
H2A H 0.2808 0.5072 0.2470 0.030 Uiso 1 1 calc R
H2B H 0.2696 0.2869 0.2632 0.030 Uiso 1 1 calc R
C3 C 0.21704(15) 0.4341(9) 0.2091(3) 0.0283(13) Uani 1 1 d .
H3A H 0.2072 0.5686 0.2070 0.034 Uiso 1 1 calc R
H3B H 0.2252 0.3947 0.1519 0.034 Uiso 1 1 calc R
C4 C 0.17921(17) 0.3105(7) 0.2399(4) 0.0263(13) Uani 1 1 d .
H4A H 0.1884 0.1751 0.2385 0.032 Uiso 1 1 calc R
H4B H 0.1535 0.3255 0.2021 0.032 Uiso 1 1 calc R
C5 C 0.16540(15) 0.3637(7) 0.3291(3) 0.0216(14) Uani 1 1 d .
H5A H 0.1544 0.4965 0.3308 0.026 Uiso 1 1 calc R
H5B H 0.1415 0.2781 0.3486 0.026 Uiso 1 1 calc R
C6 C 0.20632(15) 0.3428(6) 0.3851(3) 0.0171(12) Uani 1 1 d .
H6 H 0.2162 0.2071 0.3810 0.020 Uiso 1 1 calc R
C7 C 0.32122(15) 0.4609(6) 0.3998(3) 0.0190(13) Uani 1 1 d .
H7 H 0.3280 0.4805 0.3426 0.023 Uiso 1 1 calc R
C8 C 0.35794(16) 0.4526(6) 0.4565(3) 0.0183(13) Uani 1 1 d .
C9 C 0.40049(16) 0.4857(7) 0.4235(4) 0.0214(13) Uani 1 1 d .
H9 H 0.4036 0.5082 0.3654 0.026 Uiso 1 1 calc R
C10 C 0.43721(16) 0.4864(7) 0.4728(4) 0.0261(14) Uani 1 1 d .
H10 H 0.4656 0.5091 0.4495 0.031 Uiso 1 1 calc R
C11 C 0.43238(16) 0.4525(7) 0.5596(4) 0.0224(13) Uani 1 1 d .
H11 H 0.4579 0.4516 0.5943 0.027 Uiso 1 1 calc R
C12 C 0.39172(14) 0.4212(9) 0.5945(3) 0.0205(11) Uani 1 1 d .
C13 C 0.35248(13) 0.4194(9) 0.5435(3) 0.0161(10) Uani 1 1 d .
C14 C 0.41876(17) 0.3096(7) 0.7340(4) 0.0254(13) Uani 1 1 d .
H14 H 0.4316 0.1971 0.7045 0.031 Uiso 1 1 calc R
C15 C 0.45628(16) 0.4428(7) 0.7575(3) 0.0243(14) Uani 1 1 d .
C16 C 0.44860(18) 0.6317(8) 0.7785(4) 0.0318(14) Uani 1 1 d .
H16 H 0.4196 0.6830 0.7739 0.038 Uiso 1 1 calc R
C17 C 0.4825(2) 0.7443(9) 0.8059(4) 0.0444(18) Uani 1 1 d .
H17 H 0.4768 0.8733 0.8201 0.053 Uiso 1 1 calc R
C18 C 0.5248(2) 0.6738(10) 0.8132(4) 0.0453(18) Uani 1 1 d .
H18 H 0.5482 0.7530 0.8326 0.054 Uiso 1 1 calc R
C19 C 0.5327(2) 0.4890(10) 0.7924(4) 0.0465(19) Uani 1 1 d .
H19 H 0.5618 0.4392 0.7974 0.056 Uiso 1 1 calc R
C20 C 0.49883(16) 0.3723(9) 0.7638(4) 0.0351(16) Uani 1 1 d .
H20 H 0.5049 0.2442 0.7486 0.042 Uiso 1 1 calc R
C21 C 0.39566(19) 0.2384(8) 0.8130(4) 0.0357(16) Uani 1 1 d .
H21A H 0.3743 0.1388 0.7982 0.054 Uiso 1 1 calc R
H21B H 0.3801 0.3446 0.8397 0.054 Uiso 1 1 calc R
H21C H 0.4177 0.1863 0.8517 0.054 Uiso 1 1 calc R
C22 C 0.16288(14) 0.4141(9) 0.5092(3) 0.0191(10) Uani 1 1 d .
H22 H 0.1376 0.4123 0.4738 0.023 Uiso 1 1 calc R
C23 C 0.15520(15) 0.4490(7) 0.5965(4) 0.0211(13) Uani 1 1 d .
C24 C 0.11127(17) 0.4841(7) 0.6219(4) 0.0279(14) Uani 1 1 d .
H24 H 0.0883 0.4863 0.5814 0.033 Uiso 1 1 calc R
C25 C 0.10141(18) 0.5149(8) 0.7039(4) 0.0336(15) Uani 1 1 d .
H25 H 0.0720 0.5449 0.7197 0.040 Uiso 1 1 calc R
C26 C 0.13495(17) 0.5022(7) 0.7649(4) 0.0291(14) Uani 1 1 d .
H26 H 0.1279 0.5235 0.8219 0.035 Uiso 1 1 calc R
C27 C 0.17804(16) 0.4591(6) 0.7428(4) 0.0216(13) Uani 1 1 d .
C28 C 0.18975(15) 0.4397(7) 0.6558(3) 0.0184(12) Uani 1 1 d .
C29 C 0.20887(17) 0.4720(7) 0.8879(4) 0.0248(13) Uani 1 1 d .
H29 H 0.1994 0.6078 0.8944 0.030 Uiso 1 1 calc R
C30 C 0.17545(16) 0.3466(6) 0.9317(3) 0.0213(13) Uani 1 1 d .
C31 C 0.14954(15) 0.4181(10) 0.9965(3) 0.0295(12) Uani 1 1 d .
H31 H 0.1536 0.5462 1.0141 0.035 Uiso 1 1 calc R
C32 C 0.11818(18) 0.3075(8) 1.0356(4) 0.0326(15) Uani 1 1 d .
H32 H 0.1009 0.3593 1.0794 0.039 Uiso 1 1 calc R
C33 C 0.11203(19) 0.1207(8) 1.0106(4) 0.0357(16) Uani 1 1 d .
H33 H 0.0901 0.0444 1.0366 0.043 Uiso 1 1 calc R
C34 C 0.13778(19) 0.0457(8) 0.9479(4) 0.0363(16) Uani 1 1 d .
H34 H 0.1342 -0.0837 0.9318 0.044 Uiso 1 1 calc R
C35 C 0.16901(18) 0.1593(8) 0.9083(4) 0.0331(14) Uani 1 1 d .
H35 H 0.1862 0.1072 0.8644 0.040 Uiso 1 1 calc R
C36 C 0.25481(17) 0.4494(9) 0.9270(4) 0.0350(16) Uani 1 1 d .
H36A H 0.2755 0.5374 0.9000 0.053 Uiso 1 1 calc R
H36B H 0.2651 0.3182 0.9192 0.053 Uiso 1 1 calc R
H36C H 0.2533 0.4780 0.9867 0.053 Uiso 1 1 calc R
Cl1 Cl -0.01737(6) 0.4197(3) 0.58488(13) 0.0691(5) Uani 1 1 d .
Cl2 Cl 0.04535(6) 0.6586(3) 0.97034(13) 0.0563(5) Uani 1 1 d .
C37 C 0.0000 0.5624(12) 0.5000 0.058(3) Uani 1 2 d S
H37A H -0.0247 0.6452 0.4819 0.069 Uiso 0.50 1 calc PR
H37B H 0.0247 0.6452 0.5181 0.069 Uiso 0.50 1 calc PR
C38 C 0.0000 0.7998(12) 1.0000 0.048(3) Uani 1 2 d S
H38A H -0.0088 0.8827 0.9528 0.057 Uiso 0.50 1 calc PR
H38B H 0.0088 0.8827 1.0472 0.057 Uiso 0.50 1 calc PR
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 Cu1 O2 89.50(13) . .
O1 Cu1 N2 171.7(2) . .
O2 Cu1 N2 93.66(16) . .
O1 Cu1 N1 93.70(15) . .
O2 Cu1 N1 169.76(18) . .
N2 Cu1 N1 84.52(17) . .
C13 O1 Cu1 126.4(3) . .
C28 O2 Cu1 125.2(3) . .
C7 N1 C1 123.0(5) . .
C7 N1 Cu1 125.4(4) . .
C1 N1 Cu1 111.5(3) . .
C22 N2 C6 124.1(4) . .
C22 N2 Cu1 125.0(4) . .
C6 N2 Cu1 110.8(3) . .
C12 N3 C14 121.7(4) . .
C27 N4 C29 123.9(4) . .
N1 C1 C6 107.3(4) . .
N1 C1 C2 114.8(4) . .
C6 C1 C2 111.6(4) . .
C3 C2 C1 109.7(4) . .
C4 C3 C2 111.5(5) . .
C3 C4 C5 111.7(4) . .
C6 C5 C4 107.5(4) . .
N2 C6 C1 106.3(4) . .
N2 C6 C5 116.8(4) . .
C1 C6 C5 112.3(4) . .
N1 C7 C8 126.5(5) . .
C9 C8 C13 120.1(4) . .
C9 C8 C7 117.4(5) . .
C13 C8 C7 122.4(4) . .
C10 C9 C8 121.7(5) . .
C9 C10 C11 118.9(5) . .
C12 C11 C10 121.5(5) . .
C11 C12 N3 123.9(4) . .
C11 C12 C13 120.5(5) . .
N3 C12 C13 115.5(4) . .
O1 C13 C8 125.0(4) . .
O1 C13 C12 117.7(4) . .
C8 C13 C12 117.3(4) . .
N3 C14 C15 115.0(4) . .
N3 C14 C21 107.2(4) . .
C15 C14 C21 109.7(5) . .
C20 C15 C16 118.7(5) . .
C20 C15 C14 119.5(5) . .
C16 C15 C14 121.6(4) . .
C17 C16 C15 120.3(5) . .
C16 C17 C18 121.1(6) . .
C19 C18 C17 119.0(6) . .
C18 C19 C20 121.0(6) . .
C15 C20 C19 119.9(6) . .
N2 C22 C23 126.3(4) . .
C24 C23 C28 120.6(5) . .
C24 C23 C22 117.6(5) . .
C28 C23 C22 121.7(4) . .
C25 C24 C23 120.9(5) . .
C24 C25 C26 120.0(5) . .
C27 C26 C25 120.7(6) . .
C26 C27 N4 124.3(5) . .
C26 C27 C28 120.0(5) . .
N4 C27 C28 115.7(4) . .
O2 C28 C23 126.4(5) . .
O2 C28 C27 116.1(4) . .
C23 C28 C27 117.6(4) . .
N4 C29 C30 112.4(4) . .
N4 C29 C36 108.4(4) . .
C30 C29 C36 110.8(5) . .
C35 C30 C31 117.7(5) . .
C35 C30 C29 121.5(5) . .
C31 C30 C29 120.8(5) . .
C32 C31 C30 121.6(6) . .
C31 C32 C33 119.7(6) . .
C34 C33 C32 119.9(6) . .
C33 C34 C35 119.9(6) . .
C30 C35 C34 121.2(6) . .
Cl1 C37 Cl1 111.1(5) 2_556 .
Cl2 C38 Cl2 111.4(5) . 2_557
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.905(3) .
Cu1 O2 1.919(3) .
Cu1 N2 1.944(4) .
Cu1 N1 1.960(4) .
O1 C13 1.308(5) .
O2 C28 1.306(5) .
N1 C7 1.264(6) .
N1 C1 1.489(6) .
N2 C22 1.280(6) .
N2 C6 1.480(6) .
N3 C12 1.410(6) .
N3 C14 1.458(6) .
N4 C27 1.385(6) .
N4 C29 1.454(7) .
C1 C6 1.511(6) .
C1 C2 1.532(7) .
C2 C3 1.528(6) .
C3 C4 1.518(7) .
C4 C5 1.538(7) .
C5 C6 1.532(6) .
C7 C8 1.434(7) .
C8 C9 1.410(7) .
C8 C13 1.425(7) .
C9 C10 1.360(7) .
C10 C11 1.420(8) .
C11 C12 1.369(7) .
C12 C13 1.438(6) .
C14 C15 1.516(7) .
C14 C21 1.531(8) .
C15 C20 1.381(7) .
C15 C16 1.388(8) .
C16 C17 1.366(8) .
C17 C18 1.374(8) .
C18 C19 1.361(9) .
C19 C20 1.387(8) .
C22 C23 1.440(7) .
C23 C24 1.411(7) .
C23 C28 1.411(7) .
C24 C25 1.366(9) .
C25 C26 1.410(8) .
C26 C27 1.383(7) .
C27 C28 1.448(7) .
C29 C30 1.513(7) .
C29 C36 1.529(7) .
C30 C35 1.380(7) .
C30 C31 1.397(7) .
C31 C32 1.377(8) .
C32 C33 1.383(8) .
C33 C34 1.378(8) .
C34 C35 1.391(8) .
Cl1 C37 1.770(5) .
Cl2 C38 1.757(5) .
C37 Cl1 1.770(5) 2_556
C38 Cl2 1.757(5) 2_557
