#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:44:53 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179594 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/58/4505861.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_4505861
loop_
_publ_author_name
'Valdés-Martínez, Jesús'
'Del Rio-Ramirez, Marisa'
'Hernández-Ortega, Simón'
'Aakeröy, Christer B.'
'Helfrich, Brian'
_publ_section_title
;
 Demonstrating the Importance of Hydrogen Bonds through the Absence of
 Hydrogen Bonds
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              485
_journal_paper_doi               10.1021/cg0155393
_journal_volume                  1
_journal_year                    2001
_chemical_formula_sum            'C14 H19 Cl3 Cu N2'
_chemical_formula_weight         385.20
_chemical_name_common            'Cu2Cl6 + 2PSPG'
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 93.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.816(3)
_cell_length_b                   12.460(2)
_cell_length_c                   18.734(3)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.32
_cell_measurement_theta_min      2.35
_cell_volume                     3450.2(11)
_computing_cell_refinement       'XSCANS Ver. 2.1, (SIEMENS 1994)'
_computing_data_collection       'XSCANS Ver. 2.1, (SIEMENS 1994)'
_computing_data_reduction        'XSCANS Ver. 2.1, (SIEMENS 1994)'
_computing_molecular_graphics    'XP, SHELXTL PC Ver  4.2 (sheldrick, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.477
_diffrn_measured_fraction_theta_max 0.477
_diffrn_measurement_device_type  'Siemens P4/PC'
_diffrn_measurement_method       ω
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0745
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3178
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.722
_exptl_absorpt_correction_T_max  0.415
_exptl_absorpt_correction_T_min  0.438
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.00057(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    'none refined except H1a'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0670P)²+9.9689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1633
_reflns_number_gt                1779
_reflns_number_total             3049
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0155393_s1.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+9.9689P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+9.9689P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3450.2(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4505861
#BEGIN Tags that were not found in dictionaries:
_solved_by                       'Simon Hernandez-Ortega'
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_calc_flag
_atom_site_refinement_flags
Cu Cu -0.28389(5) 0.74019(6) 0.41380(4) 0.0415(3) Uani 1 d .
Cl1 Cl -0.42075(11) 0.72964(16) 0.36001(10) 0.0590(5) Uani 1 d .
Cl2 Cl -0.20405(12) 0.7381(2) 0.31927(10) 0.0713(6) Uani 1 d .
Cl3 Cl -0.17104(18) 0.6686(2) 0.48808(11) 0.0955(10) Uani 1 d .
N1 N -0.1634(3) 0.1270(4) 0.3700(3) 0.0362(12) Uani 1 d .
H1 H -0.154(5) 0.255(6) 0.370(4) 0.060 Uiso 1 d .
N2 N -0.1605(3) 0.3350(4) 0.3702(3) 0.0374(13) Uani 1 d .
C1 C -0.2612(4) 0.1307(5) 0.3689(3) 0.0372(15) Uani 1 d .
C2 C -0.3113(5) 0.0399(6) 0.3663(4) 0.059(2) Uani 1 d .
H2 H -0.2821 -0.0261 0.3657 0.060 Uiso 1 calc R
C3 C -0.4066(5) 0.0426(6) 0.3645(4) 0.065(2) Uani 1 d .
H3 H -0.4397 -0.0209 0.3636 0.060 Uiso 1 calc R
C4 C -0.4490(5) 0.1383(6) 0.3643(4) 0.057(2) Uani 1 d .
H4 H -0.5118 0.1397 0.3634 0.060 Uiso 1 calc R
C5 C -0.4466(5) 0.3358(6) 0.3633(4) 0.055(2) Uani 1 d .
H5 H -0.5095 0.3373 0.3612 0.060 Uiso 1 calc R
C6 C -0.4010(5) 0.4277(6) 0.3643(4) 0.060(2) Uani 1 d .
H6 H -0.4325 0.4923 0.3629 0.060 Uiso 1 calc R
C7 C -0.3067(5) 0.4288(6) 0.3672(4) 0.0521(19) Uani 1 d .
H7 H -0.2756 0.4936 0.3679 0.060 Uiso 1 calc R
C8 C -0.2601(4) 0.3332(5) 0.3690(3) 0.0356(15) Uani 1 d .
C9 C -0.3043(4) 0.2331(5) 0.3685(3) 0.0326(13) Uani 1 d .
C10 C -0.4018(4) 0.2363(6) 0.3653(3) 0.0440(16) Uani 1 d .
C11 C -0.1222(5) 0.0788(7) 0.4368(4) 0.067(2) Uani 1 d .
H11A H -0.0576 0.0781 0.4353 0.060 Uiso 1 calc R
H11B H -0.1438 0.0067 0.4413 0.060 Uiso 1 calc R
H11C H -0.1386 0.1204 0.4771 0.060 Uiso 1 calc R
C12 C -0.1311(5) 0.0743(5) 0.3052(4) 0.0503(19) Uani 1 d .
H12A H -0.0662 0.0739 0.3082 0.060 Uiso 1 calc R
H12B H -0.1532 0.1132 0.2633 0.060 Uiso 1 calc R
H12C H -0.1531 0.0019 0.3024 0.060 Uiso 1 calc R
C13 C -0.1258(5) 0.3885(6) 0.3066(4) 0.0544(19) Uani 1 d .
H13A H -0.1347 0.4646 0.3100 0.060 Uiso 1 calc R
H13B H -0.1578 0.3618 0.2640 0.060 Uiso 1 calc R
H13C H -0.0624 0.3735 0.3049 0.060 Uiso 1 calc R
C14 C -0.1171(5) 0.3789(6) 0.4384(4) 0.061(2) Uani 1 d .
H14A H -0.1226 0.4556 0.4384 0.060 Uiso 1 calc R
H14B H -0.0542 0.3595 0.4424 0.060 Uiso 1 calc R
H14C H -0.1465 0.3497 0.4782 0.060 Uiso 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'
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -2
3 1 -1
1 1 11
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_3
Cl2 Cu Cl1 99.22(8) .
Cl2 Cu Cl3 94.27(9) .
Cl1 Cu Cl3 150.16(11) .
Cl2 Cu Cl3 148.49(11) 7_466
Cl1 Cu Cl3 94.94(9) 7_466
Cl3 Cu Cl3 86.94(8) 7_466
Cu Cl3 Cu 93.06(8) 7_466
C1 N1 C11 112.3(5) .
C1 N1 C12 112.3(5) .
C11 N1 C12 111.9(5) .
C8 N2 C13 113.4(5) .
C8 N2 C14 113.0(5) .
C13 N2 C14 111.6(5) .
C8 N2 H1 95(4) .
C13 N2 H1 113(4) .
C14 N2 H1 110(4) .
C2 C1 C9 120.3(6) .
C2 C1 N1 121.3(6) .
C9 C1 N1 118.4(5) .
C1 C2 C3 121.8(7) .
C1 C2 H2 119.1 .
C3 C2 H2 119.1 .
C4 C3 C2 119.1(7) .
C4 C3 H3 120.4 .
C2 C3 H3 120.4 .
C3 C4 C10 122.4(7) .
C3 C4 H4 118.8 .
C10 C4 H4 118.8 .
C6 C5 C10 121.4(7) .
C6 C5 H5 119.3 .
C10 C5 H5 119.3 .
C5 C6 C7 121.0(7) .
C5 C6 H6 119.5 .
C7 C6 H6 119.5 .
C8 C7 C6 119.5(7) .
C8 C7 H7 120.2 .
C6 C7 H7 120.2 .
C7 C8 C9 122.2(6) .
C7 C8 N2 119.2(6) .
C9 C8 N2 118.6(5) .
C8 C9 C1 125.7(5) .
C8 C9 C10 116.1(5) .
C1 C9 C10 118.1(5) .
C4 C10 C5 122.1(6) .
C4 C10 C9 118.2(6) .
C5 C10 C9 119.7(6) .
N1 C11 H11A 109.5 .
N1 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
N1 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
N1 C12 H12A 109.5 .
N1 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
N1 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
N2 C13 H13A 109.5 .
N2 C13 H13B 109.5 .
H13A C13 H13B 109.5 .
N2 C13 H13C 109.5 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N2 C14 H14A 109.5 .
N2 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
N2 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
Cu Cl2 2.196(2) .
Cu Cl1 2.2052(19) .
Cu Cl3 2.282(2) .
Cu Cl3 2.299(2) 7_466
Cl3 Cu 2.299(2) 7_466
N1 C1 1.448(8) .
N1 C11 1.481(8) .
N1 C12 1.488(8) .
N2 C8 1.474(8) .
N2 C13 1.487(8) .
N2 C14 1.494(8) .
N2 H1 1.01(7) .
C1 C2 1.352(9) .
C1 C9 1.426(8) .
C2 C3 1.411(10) .
C2 H2 0.9300 .
C3 C4 1.349(11) .
C3 H3 0.9300 .
C4 C10 1.406(9) .
C4 H4 0.9300 .
C5 C6 1.329(10) .
C5 C10 1.406(9) .
C5 H5 0.9300 .
C6 C7 1.394(10) .
C6 H6 0.9300 .
C7 C8 1.376(9) .
C7 H7 0.9300 .
C8 C9 1.408(8) .
C9 C10 1.442(8) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
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
N2 H1 N1 1.01(7) 1.60(7) 2.592(7) 169(6)
