#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:58:01 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179433 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/30/4333064.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_4333064
loop_
_publ_author_name
'Rigamonti, Luca'
'Demartin, Francesco'
'Forni, Alessandra'
'Righetto, Stefania'
'Pasini, Alessandro'
_publ_section_title
;
 Copper(II) Complexes of salen Analogues with Two Differently Substituted
 (Push−Pull) Salicylaldehyde Moieties. A Study on the Modulation of
 Electronic Asymmetry and Nonlinear Optical Properties
;
_journal_issue                   26
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10976
_journal_page_last               10989
_journal_paper_doi               10.1021/ic0613513
_journal_volume                  45
_journal_year                    2006
_chemical_formula_sum            'C19 H18 Cl3 Cu N3 O5'
_chemical_formula_weight         538.25
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.560(10)
_cell_angle_beta                 105.250(10)
_cell_angle_gamma                103.710(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0890(10)
_cell_length_b                   11.3470(10)
_cell_length_c                   11.5330(10)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      20.17
_cell_measurement_theta_min      2.39
_cell_volume                     1099.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'omega scan'
_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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9936
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pseudoprism
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1439
_refine_ls_R_factor_gt           0.0754
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1444P)²+0.7880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2629
_reflns_number_gt                2173
_reflns_number_total             4305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0613513sup1.cif
_cod_data_source_block           1o
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4333064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Cu Cu 0.38079(9) 0.07038(8) 0.56608(8) 0.0782(4) Uani 1 1 d .
Cl1 Cl 0.0975(3) -0.3102(4) 0.6588(4) 0.1751(16) Uani 1 1 d .
Cl2 Cl 0.3317(6) -0.0702(6) 0.8517(5) 0.236(3) Uani 1 1 d .
Cl3 Cl 0.3909(5) -0.3007(6) 0.7444(7) 0.252(3) Uani 1 1 d .
O1 O 0.5146(5) 0.0021(5) 0.6526(5) 0.0828(14) Uani 1 1 d .
O2 O 0.2452(5) -0.1132(5) 0.4880(5) 0.0909(16) Uani 1 1 d .
O3 O 1.1037(7) 0.4022(6) 1.1478(7) 0.129(2) Uani 1 1 d .
O4 O 1.1081(7) 0.2122(7) 1.1336(7) 0.135(3) Uani 1 1 d .
O5 O -0.3107(7) -0.3885(8) 0.0844(7) 0.144(3) Uani 1 1 d .
N1 N 0.5333(10) 0.2549(8) 0.6655(10) 0.155(4) Uani 1 1 d .
N2 N 0.2311(7) 0.1251(6) 0.4748(6) 0.0797(16) Uani 1 1 d .
N3 N 1.0502(7) 0.2803(7) 1.0943(7) 0.098(2) Uani 1 1 d .
C1 C 0.6377(7) 0.0720(6) 0.7607(6) 0.0692(17) Uani 1 1 d .
C2 C 0.7078(7) 0.0017(7) 0.8184(7) 0.0729(18) Uani 1 1 d .
H2 H 0.6631 -0.0926 0.7813 0.087 Uiso 1 1 calc R
C3 C 0.8384(8) 0.0679(7) 0.9263(8) 0.0800(19) Uani 1 1 d .
H3 H 0.8826 0.0193 0.9625 0.096 Uiso 1 1 calc R
C4 C 0.9062(7) 0.2090(7) 0.9829(7) 0.0761(19) Uani 1 1 d .
C5 C 0.8442(8) 0.2808(7) 0.9325(8) 0.085(2) Uani 1 1 d .
H5 H 0.8921 0.3749 0.9709 0.102 Uiso 1 1 calc R
C6 C 0.7064(8) 0.2148(7) 0.8214(7) 0.0759(19) Uani 1 1 d .
C7 C 0.6530(11) 0.2931(9) 0.7653(11) 0.135(4) Uani 1 1 d .
H7 H 0.7127 0.3851 0.8063 0.162 Uiso 1 1 calc R
C8 C 0.5117(18) 0.3591(17) 0.627(2) 0.37(2) Uani 1 1 d .
H8A H 0.5318 0.4374 0.7101 0.446 Uiso 1 1 calc R
H8B H 0.5918 0.3849 0.5984 0.446 Uiso 1 1 calc R
C9 C 0.4065(12) 0.3517(10) 0.5470(16) 0.158(5) Uani 1 1 d .
H9A H 0.4313 0.3393 0.4686 0.189 Uiso 1 1 calc R
H9B H 0.4053 0.4431 0.5832 0.189 Uiso 1 1 calc R
C10 C 0.2566(13) 0.2654(10) 0.4921(15) 0.151(5) Uani 1 1 d .
H10A H 0.2088 0.2603 0.4047 0.181 Uiso 1 1 calc R
H10B H 0.2094 0.3064 0.5505 0.181 Uiso 1 1 calc R
C11 C 0.0999(9) 0.0414(8) 0.3889(9) 0.087(2) Uani 1 1 d .
H11 H 0.0385 0.0791 0.3524 0.105 Uiso 1 1 calc R
C12 C 0.0373(7) -0.1024(7) 0.3429(7) 0.0714(18) Uani 1 1 d .
C13 C -0.1034(8) -0.1717(9) 0.2395(9) 0.095(2) Uani 1 1 d .
H13 H -0.1526 -0.1231 0.2081 0.114 Uiso 1 1 calc R
C14 C -0.1697(8) -0.3106(10) 0.1840(9) 0.099(3) Uani 1 1 d .
C15 C -0.0971(9) -0.3794(9) 0.2338(9) 0.102(3) Uani 1 1 d .
H15 H -0.1430 -0.4734 0.1977 0.122 Uiso 1 1 calc R
C16 C 0.0415(8) -0.3148(8) 0.3355(8) 0.093(2) Uani 1 1 d .
H16 H 0.0886 -0.3649 0.3667 0.112 Uiso 1 1 calc R
C17 C 0.1123(7) -0.1712(7) 0.3926(7) 0.0742(19) Uani 1 1 d .
C18 C -0.3859(11) -0.3259(15) 0.0270(14) 0.177(6) Uani 1 1 d .
H18A H -0.3666 -0.2366 0.0949 0.213 Uiso 1 1 calc R
H18B H -0.4901 -0.3790 -0.0120 0.213 Uiso 1 1 calc R
H18C H -0.3542 -0.3182 -0.0423 0.213 Uiso 1 1 calc R
C19 C 0.2830(10) -0.2177(10) 0.7083(10) 0.096(3) Uani 1 1 d .
H19 H 0.303(9) -0.182(8) 0.653(8) 0.11(3) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0106 0.0060 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 Cu O1 82.71(19)
O2 Cu N1 172.6(3)
O1 Cu N1 90.6(3)
O2 Cu N2 92.5(2)
O1 Cu N2 175.0(2)
N1 Cu N2 94.2(3)
C1 O1 Cu 128.3(4)
C17 O2 Cu 128.2(4)
C18 O5 C14 118.5(8)
C7 N1 C8 115.7(8)
C7 N1 Cu 124.9(6)
C8 N1 Cu 119.4(7)
C11 N2 C10 111.8(8)
C11 N2 Cu 123.8(5)
C10 N2 Cu 124.4(6)
O3 N3 O4 122.5(7)
O3 N3 C4 119.8(7)
O4 N3 C4 117.6(7)
O1 C1 C6 123.3(6)
O1 C1 C2 119.1(6)
C6 C1 C2 117.6(6)
C3 C2 C1 121.8(6)
C2 C3 C4 119.6(7)
C5 C4 C3 121.1(6)
C5 C4 N3 118.7(6)
C3 C4 N3 120.1(7)
C4 C5 C6 120.6(6)
C7 C6 C1 122.1(7)
C7 C6 C5 118.1(7)
C1 C6 C5 119.3(7)
N1 C7 C6 128.6(8)
C9 C8 N1 128.0(11)
C8 C9 C10 131.9(13)
C9 C10 N2 115.0(9)
N2 C11 C12 127.8(7)
C17 C12 C13 121.1(7)
C17 C12 C11 122.7(6)
C13 C12 C11 116.2(7)
C14 C13 C12 120.6(8)
C15 C14 C13 118.7(7)
C15 C14 O5 116.0(8)
C13 C14 O5 125.2(9)
C14 C15 C16 122.4(8)
C15 C16 C17 119.4(8)
O2 C17 C12 124.4(6)
O2 C17 C16 117.8(7)
C12 C17 C16 117.7(6)
Cl3 C19 Cl2 108.1(6)
Cl3 C19 Cl1 112.4(5)
Cl2 C19 Cl1 107.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu O2 1.909(5)
Cu O1 1.942(5)
Cu N1 1.961(7)
Cu N2 1.966(6)
Cl1 C19 1.731(10)
Cl2 C19 1.711(11)
Cl3 C19 1.668(9)
O1 C1 1.311(8)
O2 C17 1.310(8)
O3 N3 1.195(8)
O4 N3 1.216(8)
O5 C18 1.361(13)
O5 C14 1.387(9)
N1 C7 1.274(11)
N1 C8 1.451(13)
N2 C11 1.287(9)
N2 C10 1.478(11)
N3 C4 1.453(9)
C1 C6 1.405(9)
C1 C2 1.410(10)
C2 C3 1.353(9)
C3 C4 1.391(9)
C4 C5 1.339(10)
C5 C6 1.413(10)
C6 C7 1.402(11)
C8 C9 1.169(14)
C9 C10 1.409(14)
C11 C12 1.430(10)
C12 C17 1.374(10)
C12 C13 1.395(10)
C13 C14 1.369(12)
C14 C15 1.362(12)
C15 C16 1.374(10)
C16 C17 1.419(10)
