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#$Date: 2016-03-23 20:13:54 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179403 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/00/4330085.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_4330085
loop_
_publ_author_name
'Rajnish Kumar'
'Tapas Guchhait'
'Ganesan Mani'
_publ_contact_author_address
;Department of Chemistry
Indian Institute of Technology-Kharagpur
Kharagpur, India 721 302
;
_publ_contact_author_email       gmani@chem.iitkgp.ernet.in
_publ_contact_author_fax         91-3222-282252
_publ_contact_author_name        'Mani, Ganesan.'
_publ_contact_author_phone       91-3222-282320
_publ_section_title
;
 Synthesis and X-ray Structures of Novel Macrocycles and Macrobicycles
 Containing N,N-Di(pyrrolylmethyl)-N-methylamine Moiety: Preliminary Anion
 Binding Study
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9029
_journal_page_last               9038
_journal_paper_doi               10.1021/ic3011822
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C38 H42 N10 O2'
_chemical_formula_weight         670.82
_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                105.366(8)
_cell_angle_beta                 97.274(8)
_cell_angle_gamma                101.051(8)
_cell_formula_units_Z            1
_cell_length_a                   5.2425(12)
_cell_length_b                   11.614(3)
_cell_length_c                   15.391(4)
_cell_measurement_reflns_used    10515
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.87
_cell_volume                     871.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_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  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10515
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9763
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       Prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0562
_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)+(0.0569P)²+0.0695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1397
_reflns_number_gt                1569
_reflns_number_total             3053
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic3011822_si_002_3.cif
_cod_data_source_block           phenylenemacrocycle_4
_cod_original_cell_volume        871.1(3)
_cod_database_code               4330085
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
_atom_site_disorder_group
C1 C 0.4706(5) 0.2727(3) 0.07393(19) 0.0466(7) Uani 1 1 d D .
C2 C 0.2942(6) 0.3896(3) 0.1911(2) 0.0573(8) Uani 1 1 d . .
H2 H 0.3888 0.4599 0.1812 0.069 Uiso 1 1 calc R .
C3 C 0.1335(6) 0.4040(3) 0.2597(2) 0.0522(8) Uani 1 1 d . .
C4 C 0.0944(7) 0.5073(3) 0.3189(2) 0.0762(11) Uani 1 1 d . .
H4 H 0.1737 0.5878 0.3229 0.091 Uiso 1 1 calc R .
C5 C -0.0833(7) 0.4719(3) 0.3719(2) 0.0711(10) Uani 1 1 d . .
H5 H -0.1422 0.5243 0.4179 0.085 Uiso 1 1 calc R .
C6 C -0.1563(6) 0.3462(3) 0.3447(2) 0.0504(8) Uani 1 1 d . .
C7 C -0.3502(6) 0.2567(3) 0.3720(2) 0.0576(8) Uani 1 1 d . .
H7A H -0.3797 0.2949 0.4329 0.069 Uiso 1 1 calc R .
H7B H -0.5179 0.2336 0.3297 0.069 Uiso 1 1 calc R .
C8 C -0.0434(6) 0.1714(3) 0.4511(2) 0.0615(9) Uani 1 1 d . .
H8A H 0.0931 0.2409 0.4533 0.092 Uiso 1 1 calc R .
H8B H 0.0299 0.1008 0.4460 0.092 Uiso 1 1 calc R .
H8C H -0.1159 0.1887 0.5061 0.092 Uiso 1 1 calc R .
C9 C -0.4607(6) 0.0400(3) 0.3648(2) 0.0541(8) Uani 1 1 d . .
H9A H -0.6151 0.0374 0.3217 0.065 Uiso 1 1 calc R .
H9B H -0.5110 0.0469 0.4242 0.065 Uiso 1 1 calc R .
C10 C -0.3698(5) -0.0752(3) 0.33387(19) 0.0454(7) Uani 1 1 d . .
C11 C -0.4185(6) -0.1835(3) 0.3552(2) 0.0591(9) Uani 1 1 d . .
H11 H -0.5181 -0.2009 0.3979 0.071 Uiso 1 1 calc R .
C12 C -0.2926(6) -0.2633(3) 0.3015(2) 0.0626(9) Uani 1 1 d . .
H12 H -0.2937 -0.3431 0.3024 0.075 Uiso 1 1 calc R .
C13 C -0.1664(6) -0.2037(3) 0.24704(19) 0.0490(7) Uani 1 1 d . .
C14 C -0.0135(6) -0.2444(3) 0.17980(19) 0.0525(8) Uani 1 1 d . .
H14 H 0.0094 -0.3242 0.1680 0.063 Uiso 1 1 calc R .
C15 C 0.2363(5) -0.2176(2) 0.06640(19) 0.0464(7) Uani 1 1 d D .
N1 N 0.3146(4) 0.2856(2) 0.14284(16) 0.0488(6) Uani 1 1 d . .
N2 N -0.0239(5) 0.3065(2) 0.27666(17) 0.0523(7) Uani 1 1 d D .
H1 H -0.032(5) 0.231(2) 0.2503(18) 0.063 Uiso 1 1 d D .
N3 N -0.2520(4) 0.1470(2) 0.37172(16) 0.0461(6) Uani 1 1 d . .
N4 N -0.2176(5) -0.0888(2) 0.26844(17) 0.0503(7) Uani 1 1 d D .
H3 H -0.161(5) -0.033(2) 0.2450(18) 0.060 Uiso 1 1 d D .
N5 N 0.0929(4) -0.1763(2) 0.13527(16) 0.0508(6) Uani 1 1 d . .
O1 O 0.0477(6) 0.0697(2) 0.17411(19) 0.0881(9) Uani 1 1 d D .
H1W H 0.067(7) 0.000(2) 0.153(2) 0.106 Uiso 1 1 d D .
H2W H 0.143(7) 0.124(3) 0.158(2) 0.106 Uiso 1 1 d D .
C16 C 0.4468(11) -0.1261(5) 0.0604(4) 0.0526(12) Uani 0.510(2) 1 d PD 1
H16 H 0.4892 -0.0478 0.1022 0.063 Uiso 0.510(2) 1 calc PR 1
C17 C 0.3373(13) -0.3215(6) 0.0475(5) 0.0551(15) Uani 0.510(2) 1 d PD 1
H17 H 0.3077 -0.3750 0.0827 0.066 Uiso 0.510(2) 1 calc PR 1
C18 C 0.4121(12) 0.1548(5) 0.0083(4) 0.0528(12) Uani 0.510(2) 1 d PD 1
H18 H 0.2725 0.0945 0.0121 0.063 Uiso 0.510(2) 1 calc PR 1
C19 C 0.5194(14) 0.3485(6) 0.0216(5) 0.0584(16) Uani 0.510(2) 1 d PD 1
H19 H 0.4559 0.4195 0.0323 0.070 Uiso 0.510(2) 1 calc PR 1
C16' C 0.2671(12) -0.1474(5) 0.0040(4) 0.0526(12) Uani 0.490(2) 1 d PD 2
H16' H 0.1863 -0.0819 0.0092 0.063 Uiso 0.490(2) 1 calc PR 2
C17' C 0.1860(15) -0.3335(6) 0.0099(5) 0.0551(15) Uani 0.490(2) 1 d PD 2
H17' H 0.0566 -0.3950 0.0178 0.066 Uiso 0.490(2) 1 calc PR 2
C18' C 0.5870(12) 0.1735(5) 0.0636(4) 0.0528(12) Uani 0.490(2) 1 d PD 2
H18' H 0.5663 0.1247 0.1026 0.063 Uiso 0.490(2) 1 calc PR 2
C19' C 0.6713(13) 0.3606(7) 0.0602(5) 0.0584(16) Uani 0.490(2) 1 d PD 2
H19' H 0.7111 0.4405 0.0994 0.070 Uiso 0.490(2) 1 calc PR 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C19 C1 C18' 119.3(5) . .
C19 C1 C19' 37.9(3) . .
C18' C1 C19' 101.1(4) . .
C19 C1 N1 126.4(4) . .
C18' C1 N1 114.3(3) . .
C19' C1 N1 129.0(4) . .
C19 C1 C18 102.3(4) . .
C18' C1 C18 46.7(3) . .
C19' C1 C18 115.3(5) . .
N1 C1 C18 115.6(3) . .
N1 C2 C3 123.3(3) . .
N1 C2 H2 118.3 . .
C3 C2 H2 118.3 . .
C4 C3 N2 105.8(3) . .
C4 C3 C2 131.1(3) . .
N2 C3 C2 123.1(3) . .
C3 C4 C5 108.7(3) . .
C3 C4 H4 125.7 . .
C5 C4 H4 125.7 . .
C6 C5 C4 107.9(3) . .
C6 C5 H5 126.1 . .
C4 C5 H5 126.1 . .
N2 C6 C5 106.8(3) . .
N2 C6 C7 120.5(3) . .
C5 C6 C7 132.6(3) . .
N3 C7 C6 110.5(2) . .
N3 C7 H7A 109.5 . .
C6 C7 H7A 109.5 . .
N3 C7 H7B 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 108.1 . .
N3 C8 H8A 109.5 . .
N3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N3 C9 C10 110.8(2) . .
N3 C9 H9A 109.5 . .
C10 C9 H9A 109.5 . .
N3 C9 H9B 109.5 . .
C10 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
N4 C10 C11 106.8(3) . .
N4 C10 C9 120.5(2) . .
C11 C10 C9 132.6(3) . .
C10 C11 C12 108.1(3) . .
C10 C11 H11 126.0 . .
C12 C11 H11 126.0 . .
C13 C12 C11 108.3(3) . .
C13 C12 H12 125.8 . .
C11 C12 H12 125.8 . .
N4 C13 C12 105.8(3) . .
N4 C13 C14 123.4(3) . .
C12 C13 C14 130.7(3) . .
N5 C14 C13 122.8(3) . .
N5 C14 H14 118.6 . .
C13 C14 H14 118.6 . .
C17' C15 C17 37.7(3) . .
C17' C15 N5 125.2(4) . .
C17 C15 N5 129.0(4) . .
C17' C15 C16 120.8(5) . .
C17 C15 C16 102.6(4) . .
N5 C15 C16 114.0(3) . .
C17' C15 C16' 101.8(4) . .
C17 C15 C16' 115.3(4) . .
N5 C15 C16' 115.6(3) . .
C16 C15 C16' 47.4(3) . .
C2 N1 C1 122.7(3) . .
C6 N2 C3 110.8(2) . .
C6 N2 H1 124(2) . .
C3 N2 H1 125(2) . .
C9 N3 C8 111.0(2) . .
C9 N3 C7 113.3(2) . .
C8 N3 C7 111.2(2) . .
C10 N4 C13 111.0(2) . .
C10 N4 H3 123.9(19) . .
C13 N4 H3 125.2(19) . .
C14 N5 C15 123.0(2) . .
H1W O1 H2W 115(4) . .
C18 C16 C15 118.6(5) 2_655 .
C18 C16 H16 120.7 2_655 .
C15 C16 H16 120.7 . .
C19 C17 C15 122.4(6) 2_655 .
C19 C17 H17 118.8 2_655 .
C15 C17 H17 118.8 . .
C16 C18 C1 122.7(5) 2_655 .
C16 C18 H18 118.7 2_655 .
C1 C18 H18 118.7 . .
C1 C19 C17 120.7(6) . 2_655
C1 C19 H19 119.7 . .
C17 C19 H19 119.7 2_655 .
C18' C16' C15 121.8(5) 2_655 .
C18' C16' H16' 119.1 2_655 .
C15 C16' H16' 119.1 . .
C15 C17' C19' 119.7(6) . 2_655
C15 C17' H17' 120.1 . .
C19' C17' H17' 120.1 2_655 .
C16' C18' C1 120.0(5) 2_655 .
C16' C18' H18' 120.0 2_655 .
C1 C18' H18' 120.0 . .
C1 C19' C17' 122.6(7) . 2_655
C1 C19' H19' 118.7 . .
C17' C19' H19' 118.7 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C19 1.353(7) .
C1 C18' 1.386(6) .
C1 C19' 1.398(7) .
C1 N1 1.414(3) .
C1 C18 1.420(6) .
C2 N1 1.272(3) .
C2 C3 1.427(4) .
C2 H2 0.9300 .
C3 C4 1.369(4) .
C3 N2 1.373(3) .
C4 C5 1.388(4) .
C4 H4 0.9300 .
C5 C6 1.370(4) .
C5 H5 0.9300 .
C6 N2 1.357(3) .
C6 C7 1.492(4) .
C7 N3 1.462(3) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 N3 1.459(3) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 N3 1.460(3) .
C9 C10 1.486(4) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 N4 1.358(3) .
C10 C11 1.369(4) .
C11 C12 1.394(4) .
C11 H11 0.9300 .
C12 C13 1.375(4) .
C12 H12 0.9300 .
C13 N4 1.374(3) .
C13 C14 1.426(4) .
C14 N5 1.274(3) .
C14 H14 0.9300 .
C15 C17' 1.350(7) .
C15 C17 1.385(7) .
C15 N5 1.411(3) .
C15 C16 1.409(6) .
C15 C16' 1.420(6) .
N2 H1 0.85(2) .
N4 H3 0.84(2) .
O1 H1W 0.82(2) .
O1 H2W 0.83(2) .
C16 C18 1.373(7) 2_655
C16 H16 0.9300 .
C17 C19 1.383(10) 2_655
C17 H17 0.9300 .
C18 C16 1.373(7) 2_655
C18 H18 0.9300 .
C19 C17 1.383(10) 2_655
C19 H19 0.9300 .
C16' C18' 1.373(8) 2_655
C16' H16' 0.9300 .
C17' C19' 1.391(10) 2_655
C17' H17' 0.9300 .
C18' C16' 1.373(8) 2_655
C18' H18' 0.9300 .
C19' C17' 1.391(10) 2_655
C19' H19' 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1 O1 0.85(2) 2.08(2) 2.905(3) 163(3)
N4 H3 O1 0.84(2) 2.08(2) 2.895(3) 163(3)
O1 H1W N5 0.82(2) 2.03(3) 2.823(3) 164(4)
O1 H2W N1 0.83(2) 2.01(3) 2.817(3) 163(4)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
N1 C2 C3 C4 177.9(3) .
N1 C2 C3 N2 -3.3(5) .
N2 C3 C4 C5 0.7(4) .
C2 C3 C4 C5 179.6(3) .
C3 C4 C5 C6 -0.6(4) .
C4 C5 C6 N2 0.3(4) .
C4 C5 C6 C7 -176.0(3) .
N2 C6 C7 N3 39.6(4) .
C5 C6 C7 N3 -144.5(3) .
N3 C9 C10 N4 -39.4(4) .
N3 C9 C10 C11 144.4(3) .
N4 C10 C11 C12 0.1(3) .
C9 C10 C11 C12 176.7(3) .
C10 C11 C12 C13 0.0(4) .
C11 C12 C13 N4 0.0(3) .
C11 C12 C13 C14 -179.2(3) .
N4 C13 C14 N5 1.5(4) .
C12 C13 C14 N5 -179.5(3) .
C3 C2 N1 C1 178.8(3) .
C19 C1 N1 C2 -31.2(5) .
C18' C1 N1 C2 146.7(4) .
C19' C1 N1 C2 17.1(6) .
C18 C1 N1 C2 -161.4(4) .
C5 C6 N2 C3 0.2(3) .
C7 C6 N2 C3 177.0(3) .
C4 C3 N2 C6 -0.6(3) .
C2 C3 N2 C6 -179.6(3) .
C10 C9 N3 C8 -73.0(3) .
C10 C9 N3 C7 161.0(2) .
C6 C7 N3 C9 -159.1(2) .
C6 C7 N3 C8 75.0(3) .
C11 C10 N4 C13 -0.1(3) .
C9 C10 N4 C13 -177.2(2) .
C12 C13 N4 C10 0.1(3) .
C14 C13 N4 C10 179.3(3) .
C13 C14 N5 C15 -177.7(3) .
C17' C15 N5 C14 32.3(5) .
C17 C15 N5 C14 -15.3(6) .
C16 C15 N5 C14 -147.2(4) .
C16' C15 N5 C14 160.3(4) .
C17' C15 C16 C18 4.6(7) 2_655
C17 C15 C16 C18 40.5(6) 2_655
N5 C15 C16 C18 -175.8(4) 2_655
C16' C15 C16 C18 -72.3(6) 2_655
C17' C15 C17 C19 82.1(10) 2_655
N5 C15 C17 C19 -178.4(4) 2_655
C16 C15 C17 C19 -42.5(7) 2_655
C16' C15 C17 C19 6.1(8) 2_655
C19 C1 C18 C16 41.8(7) 2_655
C18' C1 C18 C16 -77.1(7) 2_655
C19' C1 C18 C16 4.1(7) 2_655
N1 C1 C18 C16 -177.1(4) 2_655
C18' C1 C19 C17 6.2(8) 2_655
C19' C1 C19 C17 74.9(9) 2_655
N1 C1 C19 C17 -176.0(5) 2_655
C18 C1 C19 C17 -40.8(7) 2_655
C17' C15 C16' C18' -44.4(7) 2_655
C17 C15 C16' C18' -7.0(8) 2_655
N5 C15 C16' C18' 176.8(5) 2_655
C16 C15 C16' C18' 76.8(7) 2_655
C17 C15 C17' C19' -74.8(9) 2_655
N5 C15 C17' C19' 174.9(4) 2_655
C16 C15 C17' C19' -5.5(8) 2_655
C16' C15 C17' C19' 41.5(7) 2_655
C19 C1 C18' C16' -5.1(8) 2_655
C19' C1 C18' C16' -40.8(7) 2_655
N1 C1 C18' C16' 176.8(5) 2_655
C18 C1 C18' C16' 73.7(6) 2_655
C19 C1 C19' C17' -80.2(10) 2_655
C18' C1 C19' C17' 44.0(7) 2_655
N1 C1 C19' C17' 178.2(5) 2_655
C18 C1 C19' C17' -3.2(8) 2_655
