#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:22:13 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178896 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/25/4112577.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_4112577
loop_
_publ_author_name
'Shih-Sheng Sun'
'Charlotte L. Stern'
'SonBinh T. Nguyen'
'Joseph T. Hupp'
_publ_section_title
;
 Directed Assembly of Transition-Metal-Coordinated Molecular Loops and
 Squares from Salen-Type Components. Examples of Metalation-Controlled
 Structural Conversion
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6314
_journal_page_last               6326
_journal_paper_doi               10.1021/ja037378s
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C43 H40 Cl2 N4 O2'
_chemical_formula_weight         715.69
_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                 108.509(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.020(4)
_cell_length_b                   22.933(5)
_cell_length_c                   9.7801(14)
_cell_measurement_temperature    153(2)
_cell_volume                     3832.6(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17618
_diffrn_reflns_theta_full        28.83
_diffrn_reflns_theta_max         28.83
_diffrn_reflns_theta_min         1.49
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0542
_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)+(0.0840P)²+2.6803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                3598
_reflns_number_total             4612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja037378ssi20030721_010224.cif
_cod_data_source_block           compound-7
_cod_original_cell_volume        3832.7(13)
_cod_database_code               4112577
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
Cl1 Cl 0.07577(3) 0.15745(3) 0.86115(8) 0.0798(2) Uani 1 1 d .
O1 O 0.41520(7) 0.07985(5) 0.75923(13) 0.0392(3) Uani 1 1 d .
H1 H 0.4322(14) 0.0451(11) 0.760(2) 0.063(7) Uiso 1 1 d .
N1 N 0.43966(7) -0.03027(5) 0.80769(13) 0.0325(3) Uani 1 1 d .
N2 N 0.05503(10) 0.06999(8) 1.48205(19) 0.0556(4) Uani 1 1 d .
C1 C 0.46812(12) -0.18997(7) 0.7750(2) 0.0515(5) Uani 1 1 d .
H1A H 0.4457 -0.2258 0.7905 0.062 Uiso 1 1 calc R
C2 C 0.43714(11) -0.13785(7) 0.80239(19) 0.0434(4) Uani 1 1 d .
H2 H 0.3934 -0.1382 0.8369 0.052 Uiso 1 1 calc R
C3 C 0.46938(9) -0.08457(6) 0.77995(16) 0.0335(3) Uani 1 1 d .
C4 C 0.39996(9) -0.02681(6) 0.89591(16) 0.0332(3) Uani 1 1 d .
H4 H 0.3949 -0.0605 0.9488 0.040 Uiso 1 1 calc R
C5 C 0.36258(8) 0.02695(6) 0.91727(15) 0.0320(3) Uani 1 1 d .
C6 C 0.37033(9) 0.07920(6) 0.84614(16) 0.0333(3) Uani 1 1 d .
C7 C 0.33127(9) 0.13071(7) 0.86515(17) 0.0354(3) Uani 1 1 d .
C8 C 0.28795(9) 0.12768(7) 0.95944(17) 0.0377(3) Uani 1 1 d .
H8 H 0.2624 0.1620 0.9758 0.045 Uiso 1 1 calc R
C9 C 0.27998(9) 0.07631(7) 1.03207(16) 0.0360(3) Uani 1 1 d .
C10 C 0.31647(9) 0.02603(7) 1.00826(15) 0.0337(3) Uani 1 1 d .
H10 H 0.3102 -0.0093 1.0540 0.040 Uiso 1 1 calc R
C11 C 0.23419(9) 0.07617(7) 1.12825(17) 0.0384(4) Uani 1 1 d .
C12 C 0.19562(10) 0.07527(7) 1.20745(18) 0.0402(4) Uani 1 1 d .
C13 C 0.14742(9) 0.07354(7) 1.29927(18) 0.0387(4) Uani 1 1 d .
C14 C 0.12708(9) 0.02108(7) 1.34851(18) 0.0401(4) Uani 1 1 d .
H14 H 0.1441 -0.0149 1.3204 0.048 Uiso 1 1 calc R
C15 C 0.08165(10) 0.02185(8) 1.43907(19) 0.0451(4) Uani 1 1 d .
H15 H 0.0687 -0.0145 1.4725 0.054 Uiso 1 1 calc R
C16 C 0.07411(17) 0.11996(10) 1.4329(3) 0.0786(8) Uani 1 1 d .
H16 H 0.0555 0.1551 1.4616 0.094 Uiso 1 1 calc R
C17 C 0.11939(16) 0.12393(9) 1.3427(3) 0.0700(7) Uani 1 1 d .
H17 H 0.1311 0.1609 1.3110 0.084 Uiso 1 1 calc R
C18 C 0.33694(11) 0.18733(7) 0.7850(2) 0.0457(4) Uani 1 1 d .
C19 C 0.30987(17) 0.17700(11) 0.6227(2) 0.0720(7) Uani 1 1 d .
H19A H 0.3091 0.2142 0.5727 0.108 Uiso 1 1 calc R
H19B H 0.2571 0.1602 0.5925 0.108 Uiso 1 1 calc R
H19C H 0.3460 0.1500 0.5983 0.108 Uiso 1 1 calc R
C20 C 0.42196(12) 0.20948(8) 0.8363(3) 0.0587(5) Uani 1 1 d .
H20A H 0.4569 0.1786 0.8242 0.088 Uiso 1 1 calc R
H20B H 0.4365 0.2204 0.9383 0.088 Uiso 1 1 calc R
H20C H 0.4266 0.2435 0.7790 0.088 Uiso 1 1 calc R
C21 C 0.28522(14) 0.23544(9) 0.8165(3) 0.0664(6) Uani 1 1 d .
H21A H 0.2883 0.2705 0.7611 0.100 Uiso 1 1 calc R
H21B H 0.3035 0.2446 0.9197 0.100 Uiso 1 1 calc R
H21C H 0.2309 0.2219 0.7887 0.100 Uiso 1 1 calc R
C22 C 0.0000 0.11425(11) 0.7500 0.0483(6) Uani 1 2 d S
H22A H -0.0211 0.0889 0.8107 0.058 Uiso 0.50 1 calc PR
H22B H 0.0211 0.0889 0.6893 0.058 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 0.0033 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'
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
C4 N1 C3 120.52(12) . .
C15 N2 C16 116.28(15) . .
C2 C1 C1 120.04(10) . 2_656
C1 C2 C3 120.77(16) . .
C2 C3 C3 119.06(10) . 2_656
C2 C3 N1 122.46(14) . .
C3 C3 N1 118.38(8) 2_656 .
N1 C4 C5 122.10(13) . .
C10 C5 C6 119.83(13) . .
C10 C5 C4 118.41(13) . .
C6 C5 C4 121.73(13) . .
O1 C6 C5 119.52(13) . .
O1 C6 C7 119.77(13) . .
C5 C6 C7 120.72(13) . .
C8 C7 C6 116.97(13) . .
C8 C7 C18 121.62(13) . .
C6 C7 C18 121.41(13) . .
C7 C8 C9 123.19(14) . .
C10 C9 C8 118.88(13) . .
C10 C9 C11 120.76(14) . .
C8 C9 C11 120.35(14) . .
C9 C10 C5 120.35(13) . .
C12 C11 C9 179.03(18) . .
C11 C12 C13 178.35(19) . .
C17 C13 C14 117.12(15) . .
C17 C13 C12 121.52(15) . .
C14 C13 C12 121.36(15) . .
C15 C14 C13 119.09(16) . .
N2 C15 C14 124.13(16) . .
N2 C16 C17 124.08(19) . .
C13 C17 C16 119.29(18) . .
C19 C18 C7 110.42(16) . .
C19 C18 C21 107.82(18) . .
C7 C18 C21 111.22(13) . .
C19 C18 C20 110.28(17) . .
C7 C18 C20 109.47(15) . .
C21 C18 C20 107.58(17) . .
Cl1 C22 Cl1 111.33(14) . 2_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C22 1.7565(15) .
O1 C6 1.3463(17) .
N1 C4 1.2862(19) .
N1 C3 1.4155(18) .
N2 C15 1.324(2) .
N2 C16 1.329(3) .
C1 C2 1.381(2) .
C1 C1 1.384(4) 2_656
C2 C3 1.400(2) .
C3 C3 1.404(3) 2_656
C4 C5 1.451(2) .
C5 C10 1.397(2) .
C5 C6 1.415(2) .
C6 C7 1.417(2) .
C7 C8 1.386(2) .
C7 C18 1.536(2) .
C8 C9 1.406(2) .
C9 C10 1.383(2) .
C9 C11 1.435(2) .
C11 C12 1.194(2) .
C12 C13 1.435(2) .
C13 C17 1.381(3) .
C13 C14 1.388(2) .
C14 C15 1.384(2) .
C16 C17 1.382(3) .
C18 C19 1.525(3) .
C18 C21 1.537(2) .
C18 C20 1.539(3) .
C22 Cl1 1.7565(15) 2_556
