#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:57:03 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179460 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/57/4335725.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_4335725
loop_
_publ_author_name
'Ajay Pal Singh Pannu'
'James R. Stevens'
'Paul G. Plieger'
_publ_contact_author_address
;
Institute of Fundamental Sciences
Massey University
Private Bag 11 222
Palmerston North
4442
NEW ZEALAND
;
_publ_contact_author_email       p.g.plieger@massey.ac.nz
_publ_contact_author_name        P.Plieger
_publ_section_title
;
 Aryl-Linked Salicylaldoxime-Based Copper(II) Helicates and "Boxes":
 Synthesis, X-ray Analysis, and Anion Influence on Complex Structure
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9327
_journal_page_last               9337
_journal_paper_doi               10.1021/ic400829d
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C34 H46 N4 O4'
_chemical_formula_sum            'C34 H46 N4 O4'
_chemical_formula_weight         574.75
_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                 113.157(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.7501(9)
_cell_length_b                   8.7686(3)
_cell_length_c                   14.9082(12)
_cell_measurement_reflns_used    10364
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.1
_cell_measurement_theta_min      6.6
_cell_volume                     3094.9(5)
_computing_cell_refinement
; 
Rigaku CrystalClear-SM Expert 2.0 rc14 
;
_computing_data_collection
; 
Rigaku CrystalClear-SM Expert 2.0 rc14 
;
_computing_data_reduction
; 
Rigaku CrystalClear-SM Expert 2.0 rc14 
;
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXP-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
; 
Rigaku CrystalClear-SM Expert 2.0 rc14 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.0867
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16396
_diffrn_reflns_theta_full        72.07
_diffrn_reflns_theta_max         72.07
_diffrn_reflns_theta_min         6.65
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0799
_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)+(0.1288P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2075
_refine_ls_wR_factor_ref         0.2603
_reflns_number_gt                1476
_reflns_number_total             2992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic400829d_si_002_1.cif
_cod_data_source_block           CCDC926413
_cod_original_cell_volume        3094.9(3)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4335725
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.41984(9) -0.0181(2) 0.15141(15) 0.0562(7) Uani 1 1 d .
H1 H 0.4087 -0.0581 0.0974 0.084 Uiso 1 1 calc R
C11 C 0.39112(13) -0.0768(4) 0.2029(2) 0.0462(8) Uani 1 1 d .
C21 C 0.34915(13) -0.1899(4) 0.1631(2) 0.0471(8) Uani 1 1 d .
C211 C 0.33504(15) -0.2498(4) 0.0659(2) 0.0524(9) Uani 1 1 d .
H21C H 0.3057 -0.3195 0.0404 0.063 Uiso 1 1 calc R
N212 N 0.36238(12) -0.2082(3) 0.01418(19) 0.0556(8) Uani 1 1 d .
O213 O 0.34194(10) -0.2730(3) -0.07774(16) 0.0669(8) Uani 1 1 d .
H21A H 0.3607 -0.2432 -0.1077 0.100 Uiso 1 1 calc R
C31 C 0.32127(13) -0.2467(4) 0.2202(2) 0.0478(8) Uani 1 1 d .
H31A H 0.2934 -0.3202 0.1936 0.057 Uiso 1 1 calc R
C41 C 0.33374(13) -0.1973(3) 0.3148(2) 0.0466(8) Uani 1 1 d .
C411 C 0.30384(14) -0.2565(4) 0.3786(2) 0.0498(9) Uani 1 1 d .
C412 C 0.34818(14) -0.3185(4) 0.4744(2) 0.0626(10) Uani 1 1 d .
H41G H 0.3747 -0.2393 0.5068 0.094 Uiso 1 1 calc R
H41H H 0.3678 -0.4025 0.4605 0.094 Uiso 1 1 calc R
H41I H 0.3298 -0.3525 0.5157 0.094 Uiso 1 1 calc R
C413 C 0.27161(15) -0.1248(4) 0.4012(3) 0.0644(10) Uani 1 1 d .
H41D H 0.2974 -0.0434 0.4321 0.097 Uiso 1 1 calc R
H41E H 0.2544 -0.1601 0.4440 0.097 Uiso 1 1 calc R
H41F H 0.2429 -0.0884 0.3415 0.097 Uiso 1 1 calc R
C414 C 0.26225(15) -0.3840(4) 0.3300(2) 0.0603(10) Uani 1 1 d .
H41A H 0.2819 -0.4675 0.3157 0.090 Uiso 1 1 calc R
H41B H 0.2336 -0.3470 0.2705 0.090 Uiso 1 1 calc R
H41C H 0.2451 -0.4180 0.3731 0.090 Uiso 1 1 calc R
C51 C 0.37552(13) -0.0858(4) 0.3508(2) 0.0493(8) Uani 1 1 d .
H51A H 0.3849 -0.0516 0.4143 0.059 Uiso 1 1 calc R
C61 C 0.40400(13) -0.0226(4) 0.2976(2) 0.0469(8) Uani 1 1 d .
C611 C 0.44842(13) 0.0968(4) 0.3426(2) 0.0528(9) Uani 1 1 d .
H61A H 0.4745 0.0617 0.4061 0.063 Uiso 1 1 calc R
H61B H 0.4696 0.1110 0.3020 0.063 Uiso 1 1 calc R
N612 N 0.42395(12) 0.2447(3) 0.3540(2) 0.0536(8) Uani 1 1 d .
C613 C 0.4689(5) 0.3296(15) 0.4437(6) 0.064(3) Uani 0.50 1 d PU
H61F H 0.4833 0.2610 0.4982 0.095 Uiso 0.50 1 calc PR
H61G H 0.4516 0.4157 0.4607 0.095 Uiso 0.50 1 calc PR
H61H H 0.4994 0.3640 0.4271 0.095 Uiso 0.50 1 calc PR
C614 C 0.4007(6) 0.3380(19) 0.2738(11) 0.052(3) Uani 0.50 1 d PU
H61I H 0.3763 0.4110 0.2870 0.063 Uiso 0.50 1 calc PR
H61J H 0.3771 0.2759 0.2191 0.063 Uiso 0.50 1 calc PR
C615 C 0.4415(3) 0.4251(7) 0.2433(4) 0.0472(15) Uani 0.50 1 d PU
C616 C 0.4576(4) 0.5788(17) 0.2760(10) 0.054(3) Uani 0.50 1 d PU
H61C H 0.4412 0.6300 0.3128 0.064 Uiso 0.50 1 calc PR
C617 C 0.5000 0.6510(6) 0.2500 0.0622(14) Uani 1 2 d S
H61E H 0.5131 0.7481 0.2729 0.075 Uiso 0.50 1 calc PR
C618 C 0.5199(5) 0.577(2) 0.1932(11) 0.061(3) Uani 0.50 1 d PU
H61D H 0.5462 0.6285 0.1757 0.073 Uiso 0.50 1 calc PR
C619 C 0.5060(3) 0.4360(8) 0.1582(5) 0.0479(16) Uani 0.50 1 d PU
C620 C 0.4656(3) 0.3585(7) 0.1842(4) 0.0478(15) Uani 0.50 1 d PU
H62A H 0.4550 0.2600 0.1611 0.057 Uiso 0.50 1 calc PR
C623 C 0.3851(7) 0.302(2) 0.2467(11) 0.058(3) Uani 0.50 1 d PU
H62B H 0.3620 0.2188 0.2104 0.087 Uiso 0.50 1 calc PR
H62C H 0.4086 0.3365 0.2143 0.087 Uiso 0.50 1 calc PR
H62D H 0.3615 0.3837 0.2508 0.087 Uiso 0.50 1 calc PR
C624 C 0.4647(5) 0.3585(14) 0.3973(6) 0.056(2) Uani 0.50 1 d PU
H62E H 0.4937 0.3135 0.4546 0.067 Uiso 0.50 1 calc PR
H62F H 0.4466 0.4374 0.4205 0.067 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C11 O1 H1 109.5 . .
O1 C11 C61 118.4(3) . .
O1 C11 C21 121.7(3) . .
C61 C11 C21 119.9(3) . .
C31 C21 C11 118.9(3) . .
C31 C21 C211 119.5(3) . .
C11 C21 C211 121.6(3) . .
N212 C211 C21 121.2(3) . .
N212 C211 H21C 119.4 . .
C21 C211 H21C 119.4 . .
C211 N212 O213 113.2(3) . .
N212 O213 H21A 109.5 . .
C41 C31 C21 122.5(3) . .
C41 C31 H31A 118.8 . .
C21 C31 H31A 118.8 . .
C31 C41 C51 116.4(3) . .
C31 C41 C411 123.7(3) . .
C51 C41 C411 119.9(3) . .
C414 C411 C41 112.7(3) . .
C414 C411 C412 108.1(3) . .
C41 C411 C412 109.1(3) . .
C414 C411 C413 108.5(3) . .
C41 C411 C413 109.2(3) . .
C412 C411 C413 109.4(3) . .
C411 C412 H41G 109.5 . .
C411 C412 H41H 109.5 . .
H41G C412 H41H 109.5 . .
C411 C412 H41I 109.5 . .
H41G C412 H41I 109.5 . .
H41H C412 H41I 109.5 . .
C411 C413 H41D 109.5 . .
C411 C413 H41E 109.5 . .
H41D C413 H41E 109.5 . .
C411 C413 H41F 109.5 . .
H41D C413 H41F 109.5 . .
H41E C413 H41F 109.5 . .
C411 C414 H41A 109.5 . .
C411 C414 H41B 109.5 . .
H41A C414 H41B 109.5 . .
C411 C414 H41C 109.5 . .
H41A C414 H41C 109.5 . .
H41B C414 H41C 109.5 . .
C61 C51 C41 124.1(3) . .
C61 C51 H51A 118.0 . .
C41 C51 H51A 118.0 . .
C51 C61 C11 118.1(3) . .
C51 C61 C611 120.3(3) . .
C11 C61 C611 121.6(3) . .
N612 C611 C61 112.3(3) . .
N612 C611 H61A 109.2 . .
C61 C611 H61A 109.2 . .
N612 C611 H61B 109.2 . .
C61 C611 H61B 109.2 . .
H61A C611 H61B 107.9 . .
C614 N612 C624 88.2(6) . .
C614 N612 C611 118.8(7) . .
C624 N612 C611 113.5(6) . .
C614 N612 C613 112.4(6) . .
C624 N612 C613 26.6(5) . .
C611 N612 C613 107.9(5) . .
C614 N612 C623 19.4(8) . .
C624 N612 C623 107.4(7) . .
C611 N612 C623 106.6(7) . .
C613 N612 C623 131.8(7) . .
N612 C613 H61F 109.5 . .
N612 C613 H61G 109.5 . .
H61F C613 H61G 109.5 . .
N612 C613 H61H 109.5 . .
H61F C613 H61H 109.5 . .
H61G C613 H61H 109.5 . .
N612 C614 C615 116.5(10) . .
N612 C614 C624 46.6(5) . .
C615 C614 C624 78.8(6) . .
N612 C614 H61I 108.2 . .
C615 C614 H61I 108.2 . .
C624 C614 H61I 97.1 . .
N612 C614 H61J 108.2 . .
C615 C614 H61J 108.2 . .
C624 C614 H61J 150.4 . .
H61I C614 H61J 107.3 . .
C620 C615 C616 117.9(8) . .
C620 C615 C614 121.1(8) . .
C616 C615 C614 121.0(9) . .
C620 C615 C619 100.6(5) . 2_655
C616 C615 C619 66.1(5) . 2_655
C614 C615 C619 101.3(7) . 2_655
C620 C615 C618 111.9(8) . 2_655
C616 C615 C618 18.8(5) . 2_655
C614 C615 C618 123.3(9) . 2_655
C619 C615 C618 48.0(5) 2_655 2_655
C615 C616 C617 117.9(11) . .
C615 C616 H61C 121.0 . .
C617 C616 H61C 121.0 . .
C618 C617 C616 119.0(5) . .
C618 C617 H61E 120.5 . .
C616 C617 H61E 120.5 . .
C617 C618 C619 126.2(12) . .
C617 C618 H61D 116.9 . .
C619 C618 H61D 116.9 . .
C618 C619 C620 116.8(9) . .
C618 C619 C624 121.5(10) . 2_655
C620 C619 C624 121.4(7) . 2_655
C618 C619 C615 71.9(7) . 2_655
C620 C619 C615 99.8(5) . 2_655
C624 C619 C615 93.1(6) 2_655 2_655
C618 C619 C616 19.3(9) . 2_655
C620 C619 C616 120.7(7) . 2_655
C624 C619 C616 112.7(8) 2_655 2_655
C615 C619 C616 53.4(6) 2_655 2_655
C615 C620 C619 122.0(6) . .
C615 C620 H62A 119.0 . .
C619 C620 H62A 119.0 . .
N612 C623 H62B 109.5 . .
N612 C623 H62C 109.5 . .
H62B C623 H62C 109.5 . .
N612 C623 H62D 109.5 . .
H62B C623 H62D 109.5 . .
H62C C623 H62D 109.5 . .
N612 C624 C619 121.3(7) . 2_655
N612 C624 C614 45.2(6) . .
C619 C624 C614 86.7(7) 2_655 .
N612 C624 C615 112.0(5) . 2_655
C619 C624 C615 18.9(4) 2_655 2_655
C614 C624 C615 88.7(6) . 2_655
N612 C624 H62E 107.0 . .
C619 C624 H62E 107.0 2_655 .
C614 C624 H62E 150.6 . .
C615 C624 H62E 96.4 2_655 .
N612 C624 H62F 107.0 . .
C619 C624 H62F 107.0 2_655 .
C614 C624 H62F 93.2 . .
C615 C624 H62F 125.7 2_655 .
H62E C624 H62F 106.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.359(3) .
O1 H1 0.8200 .
C11 C61 1.401(4) .
C11 C21 1.414(4) .
C21 C31 1.403(4) .
C21 C211 1.448(4) .
C211 N212 1.284(4) .
C211 H21C 0.9300 .
N212 O213 1.382(3) .
O213 H21A 0.8200 .
C31 C41 1.386(4) .
C31 H31A 0.9300 .
C41 C51 1.396(4) .
C41 C411 1.531(4) .
C411 C414 1.520(4) .
C411 C412 1.535(4) .
C411 C413 1.535(5) .
C412 H41G 0.9600 .
C412 H41H 0.9600 .
C412 H41I 0.9600 .
C413 H41D 0.9600 .
C413 H41E 0.9600 .
C413 H41F 0.9600 .
C414 H41A 0.9600 .
C414 H41B 0.9600 .
C414 H41C 0.9600 .
C51 C61 1.389(4) .
C51 H51A 0.9300 .
C61 C611 1.500(4) .
C611 N612 1.481(4) .
C611 H61A 0.9700 .
C611 H61B 0.9700 .
N612 C614 1.376(18) .
N612 C624 1.408(12) .
N612 C613 1.570(11) .
N612 C623 1.597(17) .
C613 H61F 0.9600 .
C613 H61G 0.9600 .
C613 H61H 0.9600 .
C614 C615 1.508(17) .
C614 C624 1.937(17) .
C614 H61I 0.9700 .
C614 H61J 0.9700 .
C615 C620 1.389(8) .
C615 C616 1.438(16) .
C615 C619 1.560(8) 2_655
C615 C618 1.710(18) 2_655
C616 C617 1.441(16) .
C616 H61C 0.9300 .
C617 C618 1.320(19) .
C617 H61E 0.9300 .
C618 C619 1.337(18) .
C618 H61D 0.9300 .
C619 C620 1.417(8) .
C619 C624 1.486(12) 2_655
C619 C615 1.560(8) 2_655
C619 C616 1.638(13) 2_655
C620 H62A 0.9300 .
C623 H62B 0.9600 .
C623 H62C 0.9600 .
C623 H62D 0.9600 .
C624 C619 1.486(12) 2_655
C624 C615 3.813(12) 2_655
C624 H62E 0.9700 .
C624 H62F 0.9700 .
