#------------------------------------------------------------------------------
#$Date: 2025-08-21 00:40:30 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301839 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/05/4330595.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_4330595
loop_
_publ_author_name
'James J. Henkelis'
'Sarah A. Barnett'
'Lindsay P. Harding'
'Michaele J. Hardie'
_publ_section_title
;
 Coordination Polymers Utilizing N-Oxide Functionalized Host Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10657
_journal_page_last               10674
_journal_paper_doi               10.1021/ic300940k
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C45 H40 N4 O13'
_chemical_formula_weight         844.81
_chemical_name_systematic
; 
(\+-)-2,7,12-trimethoxy-3,8,13-tris(4-N-oxide-pyridyloxy)-
10,15-dihydro-5H-tribenzo[a,d,g]cyclononatriene 
dimethylformamide clathrate
;
_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                 91.286(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6996(16)
_cell_length_b                   21.173(7)
_cell_length_c                   39.052(14)
_cell_measurement_temperature    150(2)
_cell_volume                     3885(2)
_computing_cell_refinement       'CrystalClear-SM Expert(Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM Expert(Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert(Rigaku, 2009)'
_computing_molecular_graphics    'X-Seed (Barbour)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.890
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'Rigaku Saturn CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_source         'Diamond Light Source'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            36804
_diffrn_reflns_theta_full        31.70
_diffrn_reflns_theta_max         31.70
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1768
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         12838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0652
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0610P)²+0.8133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1653
_reflns_number_gt                8287
_reflns_number_total             12838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic300940k_si_002_01.cif
_cod_data_source_block           c:'L1_dmf'
_cod_database_code               4330595
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
O1 O 0.2218(3) 0.94204(6) 0.01237(3) 0.0309(3) Uani 1 1 d .
O6 O 0.1749(3) 0.51987(6) 0.08642(3) 0.0313(3) Uani 1 1 d .
O2 O 0.1628(3) 0.85777(6) -0.03579(3) 0.0304(3) Uani 1 1 d .
O9 O 0.2187(3) 0.74877(6) 0.20153(3) 0.0345(3) Uani 1 1 d .
O3 O 0.2817(3) 0.75574(6) -0.04602(3) 0.0325(3) Uani 1 1 d .
O10 O 0.1917(3) 0.87020(6) 0.18726(3) 0.0344(3) Uani 1 1 d .
O5 O 0.2122(3) 0.55139(6) 0.02218(3) 0.0333(3) Uani 1 1 d .
O7 O 0.2786(3) 0.55648(6) 0.14020(4) 0.0355(3) Uani 1 1 d .
O11 O 0.3492(3) 0.93547(7) 0.14575(3) 0.0358(3) Uani 1 1 d .
C7 C -0.4808(4) 0.72692(8) 0.03364(5) 0.0272(4) Uani 1 1 d .
H7A H -0.5542 0.7136 0.0108 0.033 Uiso 1 1 calc R
H7B H -0.6465 0.7359 0.0481 0.033 Uiso 1 1 calc R
C18 C 0.0423(4) 0.82900(8) 0.16492(5) 0.0274(4) Uani 1 1 d .
C6 C -0.3073(4) 0.78700(8) 0.02981(4) 0.0256(4) Uani 1 1 d .
C20 C -0.2908(4) 0.80732(8) 0.11824(4) 0.0258(4) Uani 1 1 d .
C19 C -0.1212(4) 0.84935(9) 0.13737(4) 0.0277(4) Uani 1 1 d .
H19 H -0.1189 0.8928 0.1312 0.033 Uiso 1 1 calc R
C21 C -0.4577(4) 0.83327(9) 0.08752(4) 0.0274(4) Uani 1 1 d .
H21A H -0.6302 0.8071 0.0837 0.033 Uiso 1 1 calc R
H21B H -0.5206 0.8767 0.0928 0.033 Uiso 1 1 calc R
C5 C -0.1544(4) 0.79412(8) -0.00035(5) 0.0275(4) Uani 1 1 d .
H5 H -0.1700 0.7627 -0.0177 0.033 Uiso 1 1 calc R
C23 C 0.2947(4) 0.81127(9) -0.05296(4) 0.0274(4) Uani 1 1 d .
C9 C -0.1325(4) 0.63748(8) 0.02845(5) 0.0274(4) Uani 1 1 d .
H9 H -0.1256 0.6477 0.0048 0.033 Uiso 1 1 calc R
C13 C -0.3223(4) 0.65735(8) 0.08448(4) 0.0262(4) Uani 1 1 d .
C15 C -0.3007(4) 0.74411(8) 0.12849(4) 0.0257(4) Uani 1 1 d .
C30 C 0.3080(4) 0.51830(9) 0.11773(5) 0.0281(4) Uani 1 1 d .
C10 C 0.0322(4) 0.58798(9) 0.04101(5) 0.0276(4) Uani 1 1 d .
C3 C 0.0441(4) 0.89300(8) 0.01966(4) 0.0258(4) Uani 1 1 d .
C2 C -0.1126(4) 0.88674(8) 0.04909(4) 0.0262(4) Uani 1 1 d .
H2 H -0.0995 0.9188 0.0661 0.031 Uiso 1 1 calc R
C35 C 0.6814(5) 0.45758(9) 0.14880(5) 0.0325(4) Uani 1 1 d .
H35 H 0.6773 0.4886 0.1663 0.039 Uiso 1 1 calc R
C12 C -0.1611(4) 0.60618(8) 0.09696(5) 0.0278(4) Uani 1 1 d .
H12 H -0.1729 0.5946 0.1204 0.033 Uiso 1 1 calc R
C8 C -0.3089(4) 0.67285(8) 0.04964(5) 0.0263(4) Uani 1 1 d .
C24 C 0.4622(4) 0.83728(8) -0.08146(4) 0.0281(4) Uani 1 1 d .
C16 C -0.1304(4) 0.72391(8) 0.15631(5) 0.0273(4) Uani 1 1 d .
H16 H -0.1363 0.6808 0.1630 0.033 Uiso 1 1 calc R
C11 C 0.0135(4) 0.57256(8) 0.07585(5) 0.0271(4) Uani 1 1 d .
C4 C 0.0182(4) 0.84576(8) -0.00540(4) 0.0265(4) Uani 1 1 d .
N2 N 0.8701(4) 0.36205(8) 0.12699(4) 0.0372(4) Uani 1 1 d .
C14 C -0.4878(4) 0.69511(8) 0.11049(5) 0.0277(4) Uani 1 1 d .
H14A H -0.5662 0.6660 0.1277 0.033 Uiso 1 1 calc R
H14B H -0.6495 0.7166 0.0987 0.033 Uiso 1 1 calc R
C31 C 0.5002(4) 0.46289(8) 0.12031(5) 0.0289(4) Uani 1 1 d .
C37 C 0.3290(4) 0.92173(9) 0.17562(5) 0.0305(4) Uani 1 1 d .
C25 C 0.4514(5) 0.90020(9) -0.09143(5) 0.0327(4) Uani 1 1 d .
H25 H 0.3289 0.9286 -0.0800 0.039 Uiso 1 1 calc R
C1 C -0.2902(4) 0.83461(8) 0.05463(4) 0.0257(4) Uani 1 1 d .
N1 N 0.7941(4) 0.88184(8) -0.13419(4) 0.0373(4) Uani 1 1 d .
O4 O 0.9497(4) 0.90255(8) -0.15867(4) 0.0534(5) Uani 1 1 d .
C22 C 0.2554(5) 0.99015(9) 0.03783(5) 0.0338(4) Uani 1 1 d .
H22A H 0.0712 1.0103 0.0417 0.051 Uiso 1 1 calc R
H22B H 0.3912 1.0219 0.0300 0.051 Uiso 1 1 calc R
H22C H 0.3268 0.9713 0.0593 0.051 Uiso 1 1 calc R
C28 C 0.6458(5) 0.79745(9) -0.09875(5) 0.0326(4) Uani 1 1 d .
H28 H 0.6587 0.7542 -0.0925 0.039 Uiso 1 1 calc R
C38 C 0.4500(5) 0.95983(9) 0.20426(5) 0.0330(4) Uani 1 1 d .
C17 C 0.0463(4) 0.76509(9) 0.17433(5) 0.0283(4) Uani 1 1 d .
O8 O 1.0407(4) 0.31398(8) 0.13004(4) 0.0530(5) Uani 1 1 d .
C27 C 0.8081(5) 0.82013(10) -0.12475(5) 0.0365(5) Uani 1 1 d .
H27 H 0.9321 0.7923 -0.1363 0.044 Uiso 1 1 calc R
C26 C 0.6157(5) 0.92176(9) -0.11751(5) 0.0376(5) Uani 1 1 d .
H26 H 0.6054 0.9649 -0.1241 0.045 Uiso 1 1 calc R
O12 O 0.7901(4) 1.07021(9) 0.28021(5) 0.0580(5) Uani 1 1 d .
N3 N 0.6789(4) 1.03593(9) 0.25587(5) 0.0427(4) Uani 1 1 d .
C29 C 0.2354(5) 0.56641(10) -0.01326(5) 0.0368(5) Uani 1 1 d .
H29A H 0.0474 0.5635 -0.0245 0.055 Uiso 1 1 calc R
H29B H 0.3657 0.5366 -0.0240 0.055 Uiso 1 1 calc R
H29C H 0.3090 0.6095 -0.0156 0.055 Uiso 1 1 calc R
C42 C 0.6600(5) 1.00441(10) 0.19740(5) 0.0370(5) Uani 1 1 d .
H42 H 0.7253 1.0094 0.1747 0.044 Uiso 1 1 calc R
C34 C 0.8668(5) 0.40741(10) 0.15164(5) 0.0356(4) Uani 1 1 d .
H34 H 0.9931 0.4045 0.1709 0.043 Uiso 1 1 calc R
C39 C 0.3558(5) 0.95503(10) 0.23765(5) 0.0383(5) Uani 1 1 d .
H39 H 0.2143 0.9248 0.2431 0.046 Uiso 1 1 calc R
C36 C 0.2393(5) 0.68286(10) 0.20941(6) 0.0413(5) Uani 1 1 d .
H36A H 0.0520 0.6669 0.2158 0.062 Uiso 1 1 calc R
H36B H 0.3750 0.6767 0.2285 0.062 Uiso 1 1 calc R
H36C H 0.3050 0.6598 0.1893 0.062 Uiso 1 1 calc R
C32 C 0.5115(5) 0.41649(9) 0.09503(5) 0.0353(4) Uani 1 1 d .
H32 H 0.3915 0.4194 0.0752 0.042 Uiso 1 1 calc R
C41 C 0.7718(5) 1.04084(10) 0.22319(6) 0.0409(5) Uani 1 1 d .
H41 H 0.9177 1.0703 0.2182 0.049 Uiso 1 1 calc R
C33 C 0.6964(5) 0.36669(10) 0.09887(5) 0.0383(5) Uani 1 1 d .
H33 H 0.7028 0.3351 0.0816 0.046 Uiso 1 1 calc R
C40 C 0.4673(5) 0.99410(11) 0.26301(6) 0.0443(5) Uani 1 1 d .
H40 H 0.3960 0.9918 0.2855 0.053 Uiso 1 1 calc R
O13 O 0.3886(4) 0.37123(9) 0.20584(4) 0.0556(5) Uani 1 1 d .
N4 N 0.6453(5) 0.28162(9) 0.21576(5) 0.0454(5) Uani 1 1 d .
C43 C 0.4588(6) 0.31700(12) 0.19806(6) 0.0478(6) Uani 1 1 d .
H43 H 0.3737 0.2991 0.1780 0.057 Uiso 1 1 calc R
C44 C 0.7859(6) 0.30568(14) 0.24672(6) 0.0550(7) Uani 1 1 d .
H44A H 0.7006 0.3462 0.2530 0.083 Uiso 1 1 calc R
H44B H 0.9890 0.3117 0.2426 0.083 Uiso 1 1 calc R
H44C H 0.7628 0.2754 0.2654 0.083 Uiso 1 1 calc R
C45 C 0.7178(8) 0.21855(14) 0.20472(7) 0.0679(8) Uani 1 1 d .
H45A H 0.6219 0.2096 0.1827 0.102 Uiso 1 1 calc R
H45B H 0.6563 0.1879 0.2218 0.102 Uiso 1 1 calc R
H45C H 0.9242 0.2154 0.2021 0.102 Uiso 1 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'
O O 0.0106 0.0060 '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
C3 O1 C22 117.07(15)
C30 O6 C11 121.15(14)
C23 O2 C4 121.62(14)
C17 O9 C36 116.74(15)
C37 O10 C18 121.76(15)
C10 O5 C29 117.09(16)
C6 C7 C8 112.79(15)
C19 C18 C17 120.71(17)
C19 C18 O10 123.45(16)
C17 C18 O10 115.55(16)
C1 C6 C5 118.82(17)
C1 C6 C7 123.86(16)
C5 C6 C7 117.32(16)
C15 C20 C19 118.58(17)
C15 C20 C21 123.48(17)
C19 C20 C21 117.94(16)
C18 C19 C20 121.27(17)
C1 C21 C20 113.89(15)
C4 C5 C6 121.34(16)
O3 C23 O2 124.90(17)
O3 C23 C24 124.04(17)
O2 C23 C24 111.06(15)
C10 C9 C8 121.88(17)
C8 C13 C12 118.81(17)
C8 C13 C14 124.05(17)
C12 C13 C14 117.04(16)
C20 C15 C16 119.45(17)
C20 C15 C14 122.89(17)
C16 C15 C14 117.65(16)
O7 C30 O6 125.49(18)
O7 C30 C31 124.18(18)
O6 C30 C31 110.32(15)
O5 C10 C9 125.65(17)
O5 C10 C11 116.16(17)
C9 C10 C11 118.19(17)
O1 C3 C2 125.76(16)
O1 C3 C4 116.12(16)
C2 C3 C4 118.11(17)
C3 C2 C1 122.15(16)
C34 C35 C31 120.13(18)
C11 C12 C13 121.10(17)
C9 C8 C13 119.21(17)
C9 C8 C7 118.27(16)
C13 C8 C7 122.52(16)
C25 C24 C28 117.66(17)
C25 C24 C23 123.36(17)
C28 C24 C23 118.96(17)
C17 C16 C15 121.81(17)
C12 C11 C10 120.79(17)
C12 C11 O6 124.07(16)
C10 C11 O6 115.09(16)
C5 C4 C3 120.52(16)
C5 C4 O2 124.21(16)
C3 C4 O2 115.13(16)
O8 N2 C33 119.31(17)
O8 N2 C34 120.33(19)
C33 N2 C34 120.36(18)
C13 C14 C15 111.59(15)
C35 C31 C32 118.49(18)
C35 C31 C30 118.65(17)
C32 C31 C30 122.85(18)
O11 C37 O10 124.58(18)
O11 C37 C38 124.09(18)
O10 C37 C38 111.33(16)
C26 C25 C24 120.71(19)
C6 C1 C2 119.00(17)
C6 C1 C21 123.26(17)
C2 C1 C21 117.73(15)
O4 N1 C27 120.11(18)
O4 N1 C26 120.40(18)
C27 N1 C26 119.48(17)
C27 C28 C24 120.58(18)
C39 C38 C42 118.08(19)
C39 C38 C37 122.90(19)
C42 C38 C37 118.97(18)
O9 C17 C16 125.04(17)
O9 C17 C18 116.89(17)
C16 C17 C18 118.03(17)
N1 C27 C28 120.88(19)
N1 C26 C25 120.69(19)
O12 N3 C41 120.8(2)
O12 N3 C40 119.8(2)
C41 N3 C40 119.42(19)
C41 C42 C38 120.2(2)
N2 C34 C35 120.3(2)
C40 C39 C38 120.3(2)
C33 C32 C31 119.9(2)
N3 C41 C42 121.5(2)
N2 C33 C32 120.79(19)
N3 C40 C39 120.5(2)
C43 N4 C45 121.4(2)
C43 N4 C44 120.9(2)
C45 N4 C44 117.7(2)
O13 C43 N4 124.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.366(2)
O1 C22 1.430(2)
O6 C30 1.362(2)
O6 C11 1.405(2)
O2 C23 1.350(2)
O2 C4 1.404(2)
O9 C17 1.366(2)
O9 C36 1.432(2)
O3 C23 1.208(2)
O10 C37 1.351(2)
O10 C18 1.410(2)
O5 C10 1.373(2)
O5 C29 1.426(2)
O7 C30 1.203(2)
O11 C37 1.208(2)
C7 C6 1.520(3)
C7 C8 1.527(3)
C18 C19 1.377(3)
C18 C17 1.402(3)
C6 C1 1.399(2)
C6 C5 1.402(2)
C20 C15 1.398(2)
C20 C19 1.399(3)
C20 C21 1.521(3)
C21 C1 1.522(3)
C5 C4 1.378(3)
C23 C24 1.484(3)
C9 C10 1.386(3)
C9 C8 1.401(3)
C13 C8 1.402(2)
C13 C12 1.403(3)
C13 C14 1.520(2)
C15 C16 1.402(3)
C15 C14 1.522(3)
C30 C31 1.483(3)
C10 C11 1.404(3)
C3 C2 1.385(2)
C3 C4 1.403(2)
C2 C1 1.403(3)
C35 C34 1.377(3)
C35 C31 1.391(3)
C12 C11 1.375(3)
C24 C25 1.389(3)
C24 C28 1.392(3)
C16 C17 1.385(3)
N2 O8 1.299(2)
N2 C33 1.357(3)
N2 C34 1.360(3)
C31 C32 1.394(3)
C37 C38 1.482(3)
C25 C26 1.370(3)
N1 O4 1.293(2)
N1 C27 1.359(3)
N1 C26 1.366(3)
C28 C27 1.371(3)
C38 C39 1.390(3)
C38 C42 1.396(3)
O12 N3 1.297(2)
N3 C41 1.362(3)
N3 C40 1.365(3)
C42 C41 1.364(3)
C39 C40 1.384(3)
C32 C33 1.372(3)
O13 C43 1.234(3)
N4 C43 1.334(3)
N4 C45 1.446(3)
N4 C44 1.457(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168337807
