#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:58:01 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179433 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/30/4333025.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4333025
loop_
_publ_author_name
'Yang, Lei'
'Houser, Robert P.'
_publ_section_title
;
 Copper(I) Coordination Chemistry of (Pyridylmethyl)amide Ligands
;
_journal_issue                   23
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9416
_journal_page_last               9422
_journal_paper_doi               10.1021/ic0612810
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C22 H32 Cl Cu N4 O2'
_chemical_formula_sum            'C22 H32 Cl Cu N4 O2'
_chemical_formula_weight         483.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.754(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.162(3)
_cell_length_b                   7.3381(16)
_cell_length_c                   15.441(3)
_cell_measurement_reflns_used    6217
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.64
_cell_volume                     1204.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL (Sheldrick, 2000)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2000)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2000)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD Bruker APEX'
_diffrn_measurement_method       '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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9069
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.042
_exptl_absorpt_correction_T_max  0.8679
_exptl_absorpt_correction_T_min  0.6929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            light
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0300
_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)+(0.0400P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0799
_reflns_number_gt                2271
_reflns_number_total             2359
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic0612810sup1.cif
_cod_data_source_block           bh5106n_(Complex_5)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4333025
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, 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
Cu1 Cu 0.0000 0.60709(4) 0.2500 0.01963(11) Uani 1 2 d S
Cl1 Cl 0.0000 0.92134(9) 0.2500 0.0531(3) Uani 1 2 d S
N1 N 0.17508(13) 0.5274(2) 0.28969(9) 0.0176(3) Uani 1 1 d .
C2 C 0.25424(18) 0.6138(2) 0.36172(12) 0.0222(4) Uani 1 1 d .
H2 H 0.2217 0.7078 0.3904 0.027 Uiso 1 1 calc R
C3 C 0.38027(18) 0.5714(3) 0.39550(12) 0.0251(4) Uani 1 1 d .
H3 H 0.4333 0.6356 0.4462 0.030 Uiso 1 1 calc R
C4 C 0.42835(17) 0.4339(3) 0.35432(12) 0.0237(4) Uani 1 1 d .
H4 H 0.5148 0.4017 0.3763 0.028 Uiso 1 1 calc R
C5 C 0.34776(16) 0.3441(3) 0.28044(12) 0.0203(4) Uani 1 1 d .
H5 H 0.3784 0.2489 0.2512 0.024 Uiso 1 1 calc R
C6 C 0.22200(16) 0.3942(2) 0.24936(11) 0.0168(3) Uani 1 1 d .
C7 C 0.12947(16) 0.3091(3) 0.16674(12) 0.0223(4) Uani 1 1 d .
H7A H 0.0464 0.3016 0.1772 0.027 Uiso 1 1 calc R
H7B H 0.1204 0.3904 0.1139 0.027 Uiso 1 1 calc R
N8 N 0.16371(15) 0.1294(2) 0.14410(11) 0.0215(3) Uani 1 1 d .
H8 H 0.136(2) 0.046(3) 0.1638(15) 0.026 Uiso 1 1 d .
C9 C 0.23283(18) 0.1038(2) 0.08706(12) 0.0221(4) Uani 1 1 d .
O10 O 0.27838(14) 0.23280(19) 0.05739(9) 0.0295(3) Uani 1 1 d .
C11 C 0.2539(2) -0.0953(3) 0.06476(13) 0.0264(4) Uani 1 1 d .
C12 C 0.3441(3) -0.1824(4) 0.14905(17) 0.0482(6) Uani 1 1 d .
H12A H 0.3579 -0.3101 0.1363 0.072 Uiso 1 1 d R
H12B H 0.3079 -0.1760 0.1994 0.072 Uiso 1 1 d R
H12C H 0.4245 -0.1170 0.1658 0.072 Uiso 1 1 d R
C13 C 0.1310(3) -0.2046(4) 0.0409(3) 0.0675(10) Uani 1 1 d .
H13A H 0.1473 -0.3307 0.0267 0.101 Uiso 1 1 d R
H13B H 0.0694 -0.1497 -0.0121 0.101 Uiso 1 1 d R
H13C H 0.0976 -0.2034 0.0927 0.101 Uiso 1 1 d R
C14 C 0.3094(4) -0.1008(4) -0.0131(2) 0.0802(13) Uani 1 1 d .
H14A H 0.3853 -0.0252 0.0018 0.120 Uiso 1 1 d R
H14B H 0.2477 -0.0540 -0.0683 0.120 Uiso 1 1 d R
H14C H 0.3311 -0.2267 -0.0232 0.120 Uiso 1 1 d 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'
Cl Cl 0.1484 0.1585 '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'
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
N1 Cu1 N1 145.12(9) . 2
N1 Cu1 Cl1 107.44(4) . .
N1 Cu1 Cl1 107.44(4) 2 .
C6 N1 C2 118.20(15) . .
C6 N1 Cu1 124.43(12) . .
C2 N1 Cu1 117.37(12) . .
N1 C2 C3 122.85(17) . .
N1 C2 H2 118.6 . .
C3 C2 H2 118.6 . .
C2 C3 C4 118.94(16) . .
C2 C3 H3 120.5 . .
C4 C3 H3 120.5 . .
C5 C4 C3 118.64(17) . .
C5 C4 H4 120.7 . .
C3 C4 H4 120.7 . .
C4 C5 C6 119.58(17) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
N1 C6 C5 121.79(15) . .
N1 C6 C7 115.35(15) . .
C5 C6 C7 122.83(15) . .
N8 C7 C6 114.73(14) . .
N8 C7 H7A 108.6 . .
C6 C7 H7A 108.6 . .
N8 C7 H7B 108.6 . .
C6 C7 H7B 108.6 . .
H7A C7 H7B 107.6 . .
C9 N8 C7 122.08(16) . .
C9 N8 H8 121.0(17) . .
C7 N8 H8 116.8(17) . .
O10 C9 N8 121.35(17) . .
O10 C9 C11 122.74(17) . .
N8 C9 C11 115.88(17) . .
C14 C11 C12 110.2(2) . .
C14 C11 C13 110.4(2) . .
C12 C11 C13 107.2(2) . .
C14 C11 C9 109.38(18) . .
C12 C11 C9 108.32(16) . .
C13 C11 C9 111.35(17) . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.9509(15) .
Cu1 N1 1.9509(15) 2
Cu1 Cl1 2.3060(9) .
N1 C6 1.348(2) .
N1 C2 1.349(2) .
C2 C3 1.378(3) .
C2 H2 0.9500 .
C3 C4 1.386(3) .
C3 H3 0.9500 .
C4 C5 1.385(3) .
C4 H4 0.9500 .
C5 C6 1.387(2) .
C5 H5 0.9500 .
C6 C7 1.510(2) .
C7 N8 1.445(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
N8 C9 1.349(2) .
N8 H8 0.79(2) .
C9 O10 1.228(2) .
C9 C11 1.535(2) .
C11 C14 1.511(3) .
C11 C12 1.522(3) .
C11 C13 1.535(3) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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
N8 H8 Cl1 0.79(2) 2.48(2) 3.1884(18) 151(2) 1_545
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
N1 Cu1 N1 C6 45.05(12) 2
Cl1 Cu1 N1 C6 -134.95(12) .
N1 Cu1 N1 C2 -135.81(13) 2
Cl1 Cu1 N1 C2 44.19(13) .
C6 N1 C2 C3 0.0(3) .
Cu1 N1 C2 C3 -179.22(14) .
N1 C2 C3 C4 -0.3(3) .
C2 C3 C4 C5 0.1(3) .
C3 C4 C5 C6 0.3(3) .
C2 N1 C6 C5 0.5(2) .
Cu1 N1 C6 C5 179.62(12) .
C2 N1 C6 C7 -177.44(15) .
Cu1 N1 C6 C7 1.7(2) .
C4 C5 C6 N1 -0.6(3) .
C4 C5 C6 C7 177.13(17) .
N1 C6 C7 N8 -158.39(15) .
C5 C6 C7 N8 23.7(2) .
C6 C7 N8 C9 -90.5(2) .
C7 N8 C9 O10 5.9(3) .
C7 N8 C9 C11 -176.05(15) .
O10 C9 C11 C14 -13.2(3) .
N8 C9 C11 C14 168.8(2) .
O10 C9 C11 C12 106.9(2) .
N8 C9 C11 C12 -71.1(2) .
O10 C9 C11 C13 -135.5(2) .
N8 C9 C11 C13 46.5(3) .
