#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:58:01 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179433 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/30/4333065.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_4333065
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            'C20 H21 Cl3 Cu N4 O4'
_chemical_formula_weight         551.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.16(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.093(3)
_cell_length_b                   7.8730(16)
_cell_length_c                   17.254(4)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      18.10
_cell_measurement_theta_min      2.40
_cell_volume                     2285.5(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SMART CCD diffractometer'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            16026
_diffrn_reflns_theta_full        23.27
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3282
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0341P)²+14.3963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1652
_reflns_number_gt                1813
_reflns_number_total             3282
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0613513sup2.cif
_cod_data_source_block           1p
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4333065
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu Cu 0.48830(6) 0.19660(13) 0.02118(6) 0.0512(3) Uiso 1 1 d .
Cl1 Cl 0.24157(18) 0.2790(4) -0.17729(17) 0.1013(10) Uani 1 1 d .
Cl2 Cl 0.19777(19) 0.3198(4) -0.02645(18) 0.1075(10) Uani 1 1 d .
Cl3 Cl 0.1697(2) 0.0040(5) -0.1064(3) 0.1554(18) Uani 1 1 d .
O1 O 0.3876(3) 0.1235(8) 0.0470(3) 0.0598(16) Uani 1 1 d .
O2 O 0.4449(3) 0.0974(8) -0.0782(3) 0.0603(16) Uani 1 1 d .
N3 N 0.2907(5) 0.0531(11) 0.3347(5) 0.066(2) Uani 1 1 d .
N1 N 0.5208(4) 0.2970(9) 0.1270(4) 0.0538(18) Uani 1 1 d .
O3 O 0.3292(5) 0.1211(12) 0.3929(4) 0.106(3) Uani 1 1 d .
N2 N 0.5793(4) 0.2899(10) -0.0209(4) 0.063(2) Uani 1 1 d .
C6 C 0.4123(5) 0.1762(11) 0.1859(5) 0.050(2) Uani 1 1 d .
O4 O 0.2281(5) -0.0219(10) 0.3361(4) 0.088(2) Uani 1 1 d .
C12 C 0.5238(5) 0.2441(10) -0.1599(5) 0.049(2) Uani 1 1 d .
C16 C 0.4091(5) 0.0833(11) -0.2169(5) 0.058(2) Uani 1 1 d .
H16 H 0.3659 0.0146 -0.2121 0.070 Uiso 1 1 calc R
C5 C 0.3859(5) 0.1555(11) 0.2564(5) 0.059(2) Uani 1 1 d .
H5 H 0.4155 0.2006 0.3022 0.070 Uiso 1 1 calc R
C4 C 0.3173(6) 0.0702(12) 0.2599(5) 0.060(2) Uani 1 1 d .
N4 N 0.4965(5) 0.2747(11) -0.3789(4) 0.076(2) Uani 1 1 d .
C15 C 0.4222(5) 0.1249(11) -0.2905(5) 0.058(2) Uani 1 1 d .
H15 H 0.3879 0.0831 -0.3342 0.069 Uiso 1 1 calc R
C14 C 0.4862(5) 0.2293(11) -0.3021(5) 0.054(2) Uani 1 1 d .
C1 C 0.3673(5) 0.1103(12) 0.1155(5) 0.055(2) Uani 1 1 d .
C20 C 0.2326(7) 0.1765(15) -0.0880(6) 0.079(3) Uiso 1 1 d .
C7 C 0.4849(5) 0.2692(10) 0.1851(5) 0.053(2) Uani 1 1 d .
H7 H 0.5089 0.3150 0.2331 0.063 Uiso 1 1 calc R
C17 C 0.4590(5) 0.1413(10) -0.1483(5) 0.049(2) Uani 1 1 d .
C11 C 0.5808(5) 0.3025(12) -0.0953(5) 0.057(2) Uani 1 1 d .
H11 H 0.6250 0.3571 -0.1083 0.069 Uiso 1 1 calc R
C2 C 0.2959(5) 0.0176(12) 0.1224(5) 0.062(3) Uani 1 1 d .
H2 H 0.2654 -0.0303 0.0778 0.074 Uiso 1 1 calc R
C3 C 0.2727(5) -0.0004(12) 0.1936(6) 0.062(3) Uani 1 1 d .
H3 H 0.2266 -0.0604 0.1973 0.074 Uiso 1 1 calc R
C18 C 0.5637(7) 0.3752(17) -0.3868(6) 0.110(4) Uani 1 1 d .
H182 H 0.6104 0.3269 -0.3556 0.132 Uiso 1 1 calc R
H181 H 0.5563 0.4887 -0.3691 0.132 Uiso 1 1 calc R
H183 H 0.5697 0.3779 -0.4411 0.132 Uiso 1 1 calc R
C9 C 0.6595(5) 0.3189(13) 0.1119(5) 0.068(3) Uani 1 1 d .
H9A H 0.7098 0.3621 0.1398 0.082 Uiso 1 1 calc R
H9B H 0.6590 0.1969 0.1198 0.082 Uiso 1 1 calc R
C13 C 0.5362(5) 0.2828(11) -0.2357(5) 0.052(2) Uani 1 1 d .
H13 H 0.5802 0.3478 -0.2414 0.062 Uiso 1 1 calc R
C8 C 0.5941(5) 0.3960(12) 0.1454(6) 0.071(3) Uani 1 1 d .
H8B H 0.6098 0.4045 0.2021 0.085 Uiso 1 1 calc R
H8A H 0.5844 0.5101 0.1246 0.085 Uiso 1 1 calc R
C10 C 0.6532(6) 0.3544(17) 0.0283(5) 0.100(4) Uani 1 1 d .
H10A H 0.6984 0.3039 0.0099 0.120 Uiso 1 1 calc R
H10B H 0.6560 0.4763 0.0210 0.120 Uiso 1 1 calc R
C19 C 0.4695(8) 0.1694(18) -0.4410(6) 0.127(5) Uani 1 1 d .
H192 H 0.4619 0.0573 -0.4217 0.153 Uiso 1 1 calc R
H191 H 0.5078 0.1655 -0.4755 0.153 Uiso 1 1 calc R
H193 H 0.4199 0.2116 -0.4692 0.153 Uiso 1 1 calc R
H20 H 0.282(7) 0.130(16) -0.075(7) 0.16(5) 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
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
O2 Cu O1 82.3(2)
O2 Cu N2 91.6(3)
O1 Cu N2 170.1(3)
O2 Cu N1 173.4(2)
O1 Cu N1 91.3(2)
N2 Cu N1 94.6(3)
C1 O1 Cu 128.7(5)
C17 O2 Cu 127.6(5)
O3 N3 O4 122.7(8)
O3 N3 C4 118.9(9)
O4 N3 C4 118.3(9)
C7 N1 C8 115.6(7)
C7 N1 Cu 123.9(6)
C8 N1 Cu 120.2(6)
C11 N2 C10 112.2(7)
C11 N2 Cu 123.3(6)
C10 N2 Cu 124.5(6)
C5 C6 C1 120.0(8)
C5 C6 C7 119.0(8)
C1 C6 C7 121.0(7)
C13 C12 C17 120.6(8)
C13 C12 C11 117.9(8)
C17 C12 C11 121.4(8)
C15 C16 C17 121.9(8)
C4 C5 C6 121.1(8)
C5 C4 C3 121.1(8)
C5 C4 N3 119.7(9)
C3 C4 N3 119.2(9)
C19 N4 C14 120.0(9)
C19 N4 C18 115.4(9)
C14 N4 C18 117.8(8)
C16 C15 C14 122.0(8)
C13 C14 C15 116.4(8)
C13 C14 N4 123.0(8)
C15 C14 N4 120.6(8)
O1 C1 C6 124.2(8)
O1 C1 C2 118.8(8)
C6 C1 C2 117.0(8)
Cl2 C20 Cl3 110.9(6)
Cl2 C20 Cl1 109.2(7)
Cl3 C20 Cl1 110.2(6)
N1 C7 C6 128.7(8)
O2 C17 C16 120.3(8)
O2 C17 C12 123.6(8)
C16 C17 C12 116.1(8)
N2 C11 C12 128.6(8)
C3 C2 C1 120.7(8)
C2 C3 C4 120.1(8)
C10 C9 C8 112.4(9)
C14 C13 C12 122.8(8)
N1 C8 C9 112.0(7)
C9 C10 N2 114.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu O2 1.912(6)
Cu O1 1.940(5)
Cu N2 1.971(7)
Cu N1 1.978(7)
Cl1 C20 1.770(11)
Cl2 C20 1.726(11)
Cl3 C20 1.727(11)
O1 C1 1.294(9)
O2 C17 1.320(9)
N3 O3 1.223(9)
N3 O4 1.226(9)
N3 C4 1.448(10)
N1 C7 1.283(10)
N1 C8 1.462(10)
N2 C11 1.292(10)
N2 C10 1.481(11)
C6 C5 1.378(11)
C6 C1 1.417(11)
C6 C7 1.443(11)
C12 C13 1.395(10)
C12 C17 1.415(11)
C12 C11 1.421(11)
C16 C15 1.367(11)
C16 C17 1.408(11)
C5 C4 1.362(11)
C4 C3 1.376(12)
N4 C19 1.368(12)
N4 C14 1.413(10)
N4 C18 1.421(12)
C15 C14 1.410(11)
C14 C13 1.370(11)
C1 C2 1.445(11)
C2 C3 1.363(11)
C9 C10 1.456(12)
C9 C8 1.476(11)
