#------------------------------------------------------------------------------
#$Date: 2020-01-31 02:18:24 +0200 (Fri, 31 Jan 2020) $
#$Revision: 247392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/78/4037877.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_4037877
loop_
_publ_author_name
'Cornelissen, Milo D.'
'Pilon, Simone'
'Steemers, Luuk'
'Wanner, Martin J.'
'Frölke, Steven'
'Zuidinga, Ed'
'Jorgensen, Steen Ingemann'
'van der Vlugt, Jarl Ivar'
'van Maarseveen, Jan H.'
_publ_section_title
;
 A covalent and modular synthesis of homo and hetero [n]rotaxanes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03030
_journal_year                    2020
_chemical_formula_sum            'C25 H38 N3 O3'
_chemical_formula_weight         428.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                105.542(6)
_cell_angle_beta                 94.855(6)
_cell_angle_gamma                96.174(6)
_cell_formula_units_Z            2
_cell_length_a                   8.7409(19)
_cell_length_b                   12.748(3)
_cell_length_c                   13.057(3)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4195
_cell_measurement_theta_min      2.7014
_cell_volume                     1383.8(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.923
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type
'Bruker ApexII Triumph monochromator sealed tube'
_diffrn_measurement_method       'Photon 50 CMOS detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.923
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31005
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.301
_diffrn_reflns_theta_min         2.643
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.755
_exptl_crystal_size_mid          0.620
_exptl_crystal_size_min          0.288
_refine_diff_density_max         1.219
_refine_diff_density_min         -1.095
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   3.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      3.084
_refine_ls_R_factor_all          0.1835
_refine_ls_R_factor_gt           0.1547
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3741
_refine_ls_wR_factor_ref         0.4082
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3596
_reflns_number_total             4634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03030_si_003.cif
_cod_data_source_block           JvM_SP_rotzax_thread_N3_0m_a
_cod_database_code               4037877
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.6233(4) 0.7547(3) 0.5603(3) 0.0359(9) Uani 1 1 d . .
O2 O 0.4020(4) 0.7883(3) 0.6303(3) 0.0353(9) Uani 1 1 d . .
O3 O 0.7586(3) 1.1561(3) 0.5337(3) 0.0375(9) Uani 1 1 d . .
N1 N 1.0063(6) 1.0965(4) 0.3479(4) 0.0567(13) Uani 1 1 d . .
N2 N 0.9107(8) 1.0692(5) 0.2734(5) 0.0747(17) Uani 1 1 d . .
N3 N 0.8181(16) 1.0350(8) 0.2015(8) 0.179(6) Uani 1 1 d . .
C1 C 0.6365(5) 0.9823(3) 0.5506(3) 0.0267(11) Uani 1 1 d . .
H1 H 0.7279 0.9706 0.5851 0.032 Uiso 1 1 calc R U
C2 C 0.6335(5) 1.0752(4) 0.5161(3) 0.0278(11) Uani 1 1 d . .
C3 C 0.5042(5) 0.9057(4) 0.5345(3) 0.0285(11) Uani 1 1 d . .
C4 C 0.5176(5) 0.8081(4) 0.5744(3) 0.0285(11) Uani 1 1 d . .
C5 C 0.9084(6) 1.1289(4) 0.5605(4) 0.0399(13) Uani 1 1 d . .
H5A H 0.9166 1.0541 0.5205 0.048 Uiso 1 1 calc R U
H5B H 0.9246 1.1343 0.6363 0.048 Uiso 1 1 calc R U
C6 C 1.0277(6) 1.2075(4) 0.5333(4) 0.0448(14) Uani 1 1 d . .
H6A H 1.0252 1.2807 0.5795 0.054 Uiso 1 1 calc R U
H6B H 1.1295 1.1873 0.5479 0.054 Uiso 1 1 calc R U
C7 C 1.0043(6) 1.2099(4) 0.4192(5) 0.0489(15) Uani 1 1 d . .
H7A H 1.0862 1.2604 0.4057 0.059 Uiso 1 1 calc R U
H7B H 0.9059 1.2349 0.4047 0.059 Uiso 1 1 calc R U
C8 C 0.3943(5) 0.6918(4) 0.6659(4) 0.0283(11) Uani 1 1 d . .
C9 C 0.3386(5) 0.5904(4) 0.5938(4) 0.0342(12) Uani 1 1 d . .
C10 C 0.3241(5) 0.4993(4) 0.6342(4) 0.0321(11) Uani 1 1 d . .
H10 H 0.2897 0.4301 0.5874 0.038 Uiso 1 1 calc R U
C11 C 0.3601(5) 0.5097(4) 0.7439(3) 0.0297(11) Uani 1 1 d . .
C12 C 0.4156(6) 0.6140(4) 0.8101(3) 0.0359(12) Uani 1 1 d . .
H12 H 0.4439 0.6219 0.8823 0.043 Uiso 1 1 calc R U
C13 C 0.4307(6) 0.7060(4) 0.7743(4) 0.0349(12) Uani 1 1 d . .
C14 C 0.3075(6) 0.5803(4) 0.4750(4) 0.0409(13) Uani 1 1 d . .
H14A H 0.2733 0.6482 0.4680 0.049 Uiso 1 1 calc R U
H14B H 0.4054 0.5749 0.4453 0.049 Uiso 1 1 calc R U
C15 C 0.1938(7) 0.4884(5) 0.4077(4) 0.0548(16) Uani 1 1 d . .
H15A H 0.0911 0.4994 0.4278 0.066 Uiso 1 1 calc R U
H15B H 0.2178 0.4203 0.4209 0.066 Uiso 1 1 calc R U
C16 C 0.1930(8) 0.4784(5) 0.2880(5) 0.0522(15) Uani 1 1 d . .
H16A H 0.2951 0.4648 0.2682 0.063 Uiso 1 1 calc R U
H16B H 0.1200 0.4148 0.2481 0.063 Uiso 1 1 calc R U
C17 C 0.1510(7) 0.5783(5) 0.2541(4) 0.0493(14) Uani 1 1 d . .
H17A H 0.0441 0.5865 0.2654 0.059 Uiso 1 1 calc R U
H17B H 0.2156 0.6434 0.2998 0.059 Uiso 1 1 calc R U
C18 C 0.1697(8) 0.5723(7) 0.1399(5) 0.077(2) Uani 1 1 d . .
H18A H 0.2747 0.5593 0.1274 0.092 Uiso 1 1 calc R U
H18B H 0.1000 0.5099 0.0941 0.092 Uiso 1 1 calc R U
C19 C 0.1383(11) 0.6730(11) 0.1083(10) 0.143(5) Uani 1 1 d . .
H19A H 0.0916 0.6456 0.0344 0.171 Uiso 1 1 calc R U
H19B H 0.0558 0.6996 0.1492 0.171 Uiso 1 1 calc R U
C20 C 0.2221(13) 0.7535(8) 0.1110(17) 0.212(10) Uani 1 1 d . .
H20A H 0.3115 0.7284 0.0774 0.254 Uiso 1 1 calc R U
H20B H 0.2588 0.7881 0.1860 0.254 Uiso 1 1 calc R U
C21 C 0.5034(7) 0.8189(4) 0.8485(4) 0.0503(15) Uani 1 1 d . .
H21A H 0.4574 0.8760 0.8255 0.060 Uiso 1 1 calc R U
H21B H 0.4802 0.8239 0.9208 0.060 Uiso 1 1 calc R U
C22 C 0.6796(7) 0.8386(5) 0.8485(5) 0.0581(16) Uani 1 1 d . .
H22A H 0.7247 0.7822 0.8734 0.070 Uiso 1 1 calc R U
H22B H 0.7018 0.8300 0.7754 0.070 Uiso 1 1 calc R U
C23 C 0.7579(8) 0.9492(5) 0.9165(5) 0.0618(17) Uani 1 1 d . .
H23A H 0.8690 0.9477 0.9225 0.074 Uiso 1 1 calc R U
H23B H 0.7269 0.9607 0.9878 0.074 Uiso 1 1 calc R U
C24 C 0.7249(9) 1.0458(5) 0.8769(6) 0.074(2) Uani 1 1 d . .
H24A H 0.6166 1.0545 0.8818 0.089 Uiso 1 1 calc R U
H24B H 0.7403 1.0293 0.8019 0.089 Uiso 1 1 calc R U
C25 C 0.8219(11) 1.1539(6) 0.9357(10) 0.116(4) Uani 1 1 d . .
H25A H 0.9306 1.1471 0.9303 0.140 Uiso 1 1 calc R U
H25B H 0.8069 1.1720 1.0108 0.140 Uiso 1 1 calc R U
C26 C 0.3484(5) 0.4116(4) 0.7838(4) 0.0342(12) Uani 1 1 d . .
C27 C 0.3788(6) 0.3110(4) 0.7230(4) 0.0447(14) Uani 1 1 d . .
H27 H 0.4071 0.3040 0.6547 0.054 Uiso 1 1 calc R U
C28 C 0.3675(8) 0.2199(5) 0.7628(5) 0.0609(17) Uani 1 1 d . .
H28 H 0.3857 0.1523 0.7203 0.073 Uiso 1 1 calc R U
C29 C 0.3295(8) 0.2293(6) 0.8643(6) 0.0664(19) Uani 1 1 d . .
H29 H 0.3229 0.1686 0.8912 0.080 Uiso 1 1 calc R U
C30 C 0.3016(8) 0.3289(6) 0.9256(5) 0.0668(19) Uani 1 1 d . .
H30 H 0.2757 0.3355 0.9945 0.080 Uiso 1 1 calc R U
C31 C 0.3112(7) 0.4196(5) 0.8869(4) 0.0517(15) Uani 1 1 d . .
H31 H 0.2926 0.4868 0.9300 0.062 Uiso 1 1 calc R U
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
C4 O2 C8 118.2(3) . .
C2 O3 C5 117.8(3) . .
N2 N1 C7 114.7(5) . .
N3 N2 N1 174.9(7) . .
C2 C1 C3 120.8(4) . .
C2 C1 H1 119.6 . .
C3 C1 H1 119.6 . .
O3 C2 C1 123.4(4) . .
O3 C2 C3 116.5(4) . 2_676
C1 C2 C3 119.9(4) . 2_676
C1 C3 C2 119.2(4) . 2_676
C1 C3 C4 117.3(4) . .
C2 C3 C4 123.5(4) 2_676 .
O1 C4 O2 123.9(4) . .
O1 C4 C3 123.5(4) . .
O2 C4 C3 112.6(4) . .
O3 C5 C6 108.3(4) . .
O3 C5 H5A 110.0 . .
C6 C5 H5A 110.0 . .
O3 C5 H5B 110.0 . .
C6 C5 H5B 110.0 . .
H5A C5 H5B 108.4 . .
C7 C6 C5 113.5(4) . .
C7 C6 H6A 108.9 . .
C5 C6 H6A 108.9 . .
C7 C6 H6B 108.9 . .
C5 C6 H6B 108.9 . .
H6A C6 H6B 107.7 . .
C6 C7 N1 108.9(4) . .
C6 C7 H7A 109.9 . .
N1 C7 H7A 109.9 . .
C6 C7 H7B 109.9 . .
N1 C7 H7B 109.9 . .
H7A C7 H7B 108.3 . .
C13 C8 C9 123.1(4) . .
C13 C8 O2 117.1(4) . .
C9 C8 O2 119.6(4) . .
C8 C9 C10 117.3(4) . .
C8 C9 C14 120.1(4) . .
C10 C9 C14 122.4(4) . .
C9 C10 C11 121.6(4) . .
C9 C10 H10 119.2 . .
C11 C10 H10 119.2 . .
C12 C11 C10 117.2(4) . .
C12 C11 C26 122.3(4) . .
C10 C11 C26 120.4(4) . .
C13 C12 C11 123.3(4) . .
C13 C12 H12 118.4 . .
C11 C12 H12 118.4 . .
C12 C13 C8 117.5(4) . .
C12 C13 C21 121.7(4) . .
C8 C13 C21 120.4(4) . .
C15 C14 C9 118.4(4) . .
C15 C14 H14A 107.7 . .
C9 C14 H14A 107.7 . .
C15 C14 H14B 107.7 . .
C9 C14 H14B 107.7 . .
H14A C14 H14B 107.1 . .
C14 C15 C16 112.4(4) . .
C14 C15 H15A 109.1 . .
C16 C15 H15A 109.1 . .
C14 C15 H15B 109.1 . .
C16 C15 H15B 109.1 . .
H15A C15 H15B 107.9 . .
C17 C16 C15 115.2(5) . .
C17 C16 H16A 108.5 . .
C15 C16 H16A 108.5 . .
C17 C16 H16B 108.5 . .
C15 C16 H16B 108.5 . .
H16A C16 H16B 107.5 . .
C18 C17 C16 114.3(5) . .
C18 C17 H17A 108.7 . .
C16 C17 H17A 108.7 . .
C18 C17 H17B 108.7 . .
C16 C17 H17B 108.7 . .
H17A C17 H17B 107.6 . .
C19 C18 C17 114.4(7) . .
C19 C18 H18A 108.7 . .
C17 C18 H18A 108.7 . .
C19 C18 H18B 108.7 . .
C17 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
C20 C19 C18 130.8(10) . .
C20 C19 H19A 104.5 . .
C18 C19 H19A 104.6 . .
C20 C19 H19B 104.6 . .
C18 C19 H19B 104.6 . .
H19A C19 H19B 105.7 . .
C19 C20 C25 125.3(12) . 2_676
C19 C20 H20A 106.0 . .
C25 C20 H20A 106.0 2_676 .
C19 C20 H20B 106.0 . .
C25 C20 H20B 106.0 2_676 .
H20A C20 H20B 106.3 . .
C22 C21 C13 112.3(4) . .
C22 C21 H21A 109.1 . .
C13 C21 H21A 109.1 . .
C22 C21 H21B 109.1 . .
C13 C21 H21B 109.1 . .
H21A C21 H21B 107.9 . .
C23 C22 C21 115.2(6) . .
C23 C22 H22A 108.5 . .
C21 C22 H22A 108.5 . .
C23 C22 H22B 108.5 . .
C21 C22 H22B 108.5 . .
H22A C22 H22B 107.5 . .
C22 C23 C24 115.9(5) . .
C22 C23 H23A 108.3 . .
C24 C23 H23A 108.3 . .
C22 C23 H23B 108.3 . .
C24 C23 H23B 108.3 . .
H23A C23 H23B 107.4 . .
C23 C24 C25 115.6(7) . .
C23 C24 H24A 108.4 . .
C25 C24 H24A 108.4 . .
C23 C24 H24B 108.4 . .
C25 C24 H24B 108.4 . .
H24A C24 H24B 107.4 . .
C24 C25 C20 111.1(10) . 2_676
C24 C25 H25A 109.4 . .
C20 C25 H25A 109.4 2_676 .
C24 C25 H25B 109.4 . .
C20 C25 H25B 109.4 2_676 .
H25A C25 H25B 108.0 . .
C27 C26 C31 118.0(5) . .
C27 C26 C11 122.0(4) . .
C31 C26 C11 120.0(5) . .
C26 C27 C28 120.8(5) . .
C26 C27 H27 119.6 . .
C28 C27 H27 119.6 . .
C29 C28 C27 120.3(6) . .
C29 C28 H28 119.8 . .
C27 C28 H28 119.8 . .
C30 C29 C28 119.3(5) . .
C30 C29 H29 120.4 . .
C28 C29 H29 120.4 . .
C29 C30 C31 121.0(5) . .
C29 C30 H30 119.5 . .
C31 C30 H30 119.5 . .
C30 C31 C26 120.6(6) . .
C30 C31 H31 119.7 . .
C26 C31 H31 119.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.203(5) .
O2 C4 1.337(6) .
O2 C8 1.423(5) .
O3 C2 1.378(5) .
O3 C5 1.429(6) .
N1 N2 1.177(8) .
N1 C7 1.498(7) .
N2 N3 1.141(11) .
C1 C2 1.378(6) .
C1 C3 1.393(6) .
C1 H1 0.9300 .
C2 C3 1.399(6) 2_676
C3 C2 1.399(6) 2_676
C3 C4 1.484(6) .
C5 C6 1.499(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.496(8) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C13 1.383(6) .
C8 C9 1.388(7) .
C9 C10 1.396(6) .
C9 C14 1.520(7) .
C10 C11 1.408(6) .
C10 H10 0.9300 .
C11 C12 1.387(7) .
C11 C26 1.476(6) .
C12 C13 1.372(6) .
C12 H12 0.9300 .
C13 C21 1.538(7) .
C14 C15 1.478(8) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.532(8) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.527(7) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 C18 1.496(8) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.494(11) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 C20 1.186(13) .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C20 C25 1.535(14) 2_676
C20 H20A 0.9700 .
C20 H20B 0.9700 .
C21 C22 1.534(9) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 C23 1.504(9) .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C23 C24 1.503(8) .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C25 1.509(11) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 C20 1.535(14) 2_676
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C27 1.381(7) .
C26 C31 1.391(7) .
C27 C28 1.391(7) .
C27 H27 0.9300 .
C28 C29 1.371(9) .
C28 H28 0.9300 .
C29 C30 1.366(10) .
C29 H29 0.9300 .
C30 C31 1.378(8) .
C30 H30 0.9300 .
C31 H31 0.9300 .
