#------------------------------------------------------------------------------
#$Date: 2020-08-27 02:17:12 +0300 (Thu, 27 Aug 2020) $
#$Revision: 255673 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/87/4038722.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_4038722
loop_
_publ_author_name
'Li, Jing'
'Han, Xiao-Ni'
'Zhou, He-Ye'
'Han, Ying'
'Chen, Chuan-Feng'
_publ_section_title
;
 Helic[1]triptycene[3]arene: Synthesis, Complexation and Formation of
 [2]Rotaxane Shuttle.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01558
_journal_year                    2020
_chemical_formula_moiety         'C50 H48 O8, C6 H8 N2'
_chemical_formula_sum            'C56 H56 N2 O8'
_chemical_formula_weight         885.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.45320(10)
_cell_length_b                   25.5222(2)
_cell_length_c                   16.78170(10)
_cell_measurement_reflns_used    13694
_cell_measurement_temperature    170.00(11)
_cell_measurement_theta_max      75.0510
_cell_measurement_theta_min      3.4560
_cell_volume                     5762.08(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -55.00  24.00   0.50    0.10    --  -47.20  50.00  -4.00  158
  2  ω   -120.00 -35.00   0.50    0.10    --  -47.20 -50.00-150.00  170
  3  ω     45.00  78.00   0.50    0.10    --   47.20  50.00  -4.00   66
  4  ω    -16.00  34.00   0.50    0.10    --   47.20 -50.00-150.00  100
  5  ω    -69.00 -44.00   0.50    0.50    --  -99.00  50.00  -4.00   50
  6  ω   -165.00 -85.00   0.50    0.50    --  -99.00 -50.00-150.00  160
  7  ω     93.00 118.00   0.50    0.50    --  103.25  50.00  -4.00   50
  8  ω     31.00 116.00   0.50    0.50    --  103.25 -50.00-150.00  170
  9  ω   -117.00 -89.00   0.50    0.10    --  -47.20-125.00 -30.00   56
 10  ω   -119.00 -73.00   0.50    0.10    --  -47.20-125.00   0.00   92
 11  ω   -113.00 -24.00   0.50    0.50    --  -99.00  15.00-180.00  178
 12  ω   -110.00 -46.00   0.50    0.50    --  -99.00  45.00 120.00  128
 13  ω   -111.00 -65.00   0.50    0.50    --  -99.00  30.00   0.00   92
 14  ω   -166.00-117.00   0.50    0.50    --  -99.00-125.00   0.00   98
 15  ω    -97.00 -71.00   0.50    0.50    --  -99.00-125.00   0.00   52
 16  ω    129.00 154.00   0.50    0.50    --  103.25  45.00-150.00   50
 17  ω     34.00  92.00   0.50    0.50    --  103.25 -94.00  30.00  116
 18  ω     41.00 103.00   0.50    0.50    --  103.25 -30.00   0.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1129878000
_diffrn_orient_matrix_UB_12      0.0078155000
_diffrn_orient_matrix_UB_13      -0.0087308000
_diffrn_orient_matrix_UB_21      -0.0001582000
_diffrn_orient_matrix_UB_22      -0.0362260000
_diffrn_orient_matrix_UB_23      -0.0733973000
_diffrn_orient_matrix_UB_31      -0.0184580000
_diffrn_orient_matrix_UB_32      -0.0476886000
_diffrn_orient_matrix_UB_33      0.0543922000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19657
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.215
_diffrn_reflns_theta_min         3.463
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale colourless'
_exptl_crystal_density_diffrn    1.020
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5669
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0817P)²+7.4168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5099
_reflns_number_total             5669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c01558_si_002.cif
_cod_data_source_block           tx1739_sq
_cod_database_code               4038722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_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.
;
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C28-C27 = C28-C28_$1 = C28_$1-C27_$1
 1.54 with sigma of 0.01
 C26-C27 = C26_$1-C27_$1
 1.46 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B), C27(H27A,H27B), C28(H28A,H28B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C9(H9), C13(H13), C16(H16), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.393
_oxdiff_exptl_absorpt_empirical_full_min 0.655
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70079(10) 0.81818(7) 0.21391(9) 0.0562(4) Uani 1 1 d . . . . .
O2 O 0.81186(11) 0.64446(6) 0.34726(11) 0.0593(4) Uani 1 1 d . . . . .
O3 O 0.54597(11) 0.77409(5) 0.50289(8) 0.0475(4) Uani 1 1 d . . . . .
O4 O 0.51177(11) 0.58675(5) 0.52372(7) 0.0434(3) Uani 1 1 d . . . . .
C1 C 0.52743(15) 0.82074(8) 0.17097(12) 0.0430(4) Uani 1 1 d . . . . .
H1 H 0.546617 0.821582 0.117751 0.052 Uiso 1 1 calc R . . . .
C2 C 0.60020(14) 0.81986(8) 0.22995(12) 0.0423(4) Uani 1 1 d . . . . .
C3 C 0.57340(14) 0.82040(7) 0.31029(11) 0.0401(4) Uani 1 1 d . . . . .
C4 C 0.65088(15) 0.81848(7) 0.37650(12) 0.0424(4) Uani 1 1 d . . . . .
H4A H 0.712841 0.833219 0.357249 0.051 Uiso 1 1 calc R . . . .
H4B H 0.628471 0.839545 0.421120 0.051 Uiso 1 1 calc R . . . .
C5 C 0.66844(13) 0.76272(7) 0.40417(11) 0.0387(4) Uani 1 1 d . . . . .
C6 C 0.73689(14) 0.73094(8) 0.36557(13) 0.0439(4) Uani 1 1 d . . . . .
H6 H 0.775319 0.744946 0.324734 0.053 Uiso 1 1 calc R . . . .
C7 C 0.74933(13) 0.67866(8) 0.38654(13) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.69501(14) 0.65731(7) 0.44923(11) 0.0395(4) Uani 1 1 d . . . . .
C9 C 0.62841(15) 0.68942(7) 0.48955(11) 0.0407(4) Uani 1 1 d . . . . .
H9 H 0.593052 0.675980 0.532551 0.049 Uiso 1 1 calc R . . . .
C10 C 0.61358(14) 0.74133(7) 0.46679(11) 0.0386(4) Uani 1 1 d . . . . .
C11 C 0.70362(15) 0.59955(7) 0.46981(12) 0.0428(4) Uani 1 1 d . . . . .
H11A H 0.692890 0.594655 0.526474 0.051 Uiso 1 1 calc R . . . .
H11B H 0.769873 0.587147 0.457017 0.051 Uiso 1 1 calc R . . . .
C12 C 0.62685(13) 0.56815(7) 0.42297(10) 0.0346(4) Uani 1 1 d . . . . .
C13 C 0.65079(13) 0.54517(6) 0.34993(10) 0.0328(4) Uani 1 1 d . . . . .
H13 H 0.715836 0.546515 0.331303 0.039 Uiso 1 1 calc R . . . .
C14 C 0.57819(12) 0.52036(6) 0.30499(9) 0.0294(3) Uani 1 1 d . . . . .
C15 C 0.48038(12) 0.51909(6) 0.33247(9) 0.0294(3) Uani 1 1 d . . . . .
C16 C 0.45521(13) 0.54012(7) 0.40584(10) 0.0326(4) Uani 1 1 d . . . . .
H16 H 0.390333 0.538034 0.424709 0.039 Uiso 1 1 calc R . . . .
C17 C 0.52913(14) 0.56448(7) 0.45085(10) 0.0343(4) Uani 1 1 d . . . . .
C18 C 0.59124(12) 0.49237(6) 0.22509(9) 0.0301(3) Uani 1 1 d . . . . .
H18 H 0.660159 0.492394 0.206193 0.036 Uiso 1 1 calc R . . . .
C19 C 0.54927(12) 0.43735(6) 0.23678(9) 0.0305(4) Uani 1 1 d . . . . .
C20 C 0.59865(14) 0.39065(7) 0.22365(10) 0.0375(4) Uani 1 1 d . . . . .
H20 H 0.664233 0.390603 0.206141 0.045 Uiso 1 1 calc R . . . .
C21 C 0.54864(16) 0.34358(7) 0.23705(11) 0.0436(4) Uani 1 1 d . . . . .
H21 H 0.581186 0.311930 0.228452 0.052 Uiso 1 1 calc R . . . .
C22 C 0.73001(18) 0.81984(12) 0.13216(15) 0.0655(7) Uani 1 1 d . . . . .
H22A H 0.701539 0.790567 0.104400 0.098 Uiso 1 1 calc GR . . . .
H22B H 0.801160 0.818187 0.128593 0.098 Uiso 1 1 calc GR . . . .
H22C H 0.706975 0.851865 0.108514 0.098 Uiso 1 1 calc GR . . . .
C23 C 0.8729(2) 0.66479(14) 0.2859(2) 0.0946(11) Uani 1 1 d . . . . .
H23A H 0.832018 0.681150 0.246112 0.142 Uiso 1 1 calc GR . . . .
H23B H 0.910164 0.636808 0.262071 0.142 Uiso 1 1 calc GR . . . .
H23C H 0.917794 0.690202 0.307844 0.142 Uiso 1 1 calc GR . . . .
C24 C 0.4759(2) 0.75099(11) 0.55524(16) 0.0745(8) Uani 1 1 d . . . . .
H24A H 0.442130 0.722975 0.528344 0.112 Uiso 1 1 calc GR . . . .
H24B H 0.428484 0.776920 0.571654 0.112 Uiso 1 1 calc GR . . . .
H24C H 0.509752 0.737412 0.601199 0.112 Uiso 1 1 calc GR . . . .
C25 C 0.41360(16) 0.58468(8) 0.55399(11) 0.0464(5) Uani 1 1 d . . . . .
H25A H 0.369560 0.602654 0.518229 0.070 Uiso 1 1 calc GR . . . .
H25B H 0.411514 0.601198 0.605361 0.070 Uiso 1 1 calc GR . . . .
H25C H 0.393193 0.548784 0.558919 0.070 Uiso 1 1 calc GR . . . .
N1 N 0.2824(4) 0.67556(15) 0.4221(3) 0.1414(17) Uani 1 1 d . . . . .
C26 C 0.3362(6) 0.67150(19) 0.3706(2) 0.177(4) Uani 1 1 d D . . . .
C27 C 0.3840(5) 0.6663(2) 0.2919(2) 0.210(4) Uani 1 1 d D . . . .
H27A H 0.366169 0.632589 0.269259 0.252 Uiso 1 1 calc R . . . .
H27B H 0.358156 0.693273 0.256839 0.252 Uiso 1 1 calc R . . . .
C28 C 0.4926(4) 0.6705(2) 0.2945(3) 0.301(9) Uani 1 1 d D . . . .
H28A H 0.523608 0.640626 0.320206 0.361 Uiso 1 1 calc R . . . .
H28B H 0.514965 0.702755 0.319283 0.361 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 0.0181 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
_geom_angle_publ_flag
C2 O1 C22 117.16(17) . . ?
C7 O2 C23 118.0(2) . . ?
C10 O3 C24 117.38(16) . . ?
C17 O4 C25 117.68(15) . . ?
C2 C1 C3 121.61(19) . 2_655 ?
O1 C2 C1 123.45(18) . . ?
O1 C2 C3 116.24(17) . . ?
C1 C2 C3 120.32(19) . . ?
C1 C3 C2 118.04(18) 2_655 . ?
C1 C3 C4 120.10(18) 2_655 . ?
C2 C3 C4 121.81(18) . . ?
C5 C4 C3 111.11(15) . . ?
C6 C5 C4 120.61(18) . . ?
C6 C5 C10 118.30(18) . . ?
C10 C5 C4 121.04(17) . . ?
C5 C6 C7 121.52(19) . . ?
O2 C7 C6 124.0(2) . . ?
O2 C7 C8 115.69(18) . . ?
C6 C7 C8 120.25(18) . . ?
C7 C8 C11 120.78(18) . . ?
C9 C8 C7 118.40(18) . . ?
C9 C8 C11 120.72(18) . . ?
C8 C9 C10 121.30(19) . . ?
O3 C10 C5 116.34(17) . . ?
O3 C10 C9 123.49(18) . . ?
C9 C10 C5 120.18(18) . . ?
C8 C11 C12 109.97(14) . . ?
C13 C12 C11 121.11(17) . . ?
C13 C12 C17 118.85(15) . . ?
C17 C12 C11 119.94(16) . . ?
C14 C13 C12 120.43(16) . . ?
C13 C14 C15 119.68(15) . . ?
C13 C14 C18 127.52(15) . . ?
C15 C14 C18 112.80(14) . . ?
C14 C15 C18 113.38(14) . 2_655 ?
C16 C15 C14 121.05(15) . . ?
C16 C15 C18 125.57(15) . 2_655 ?
C15 C16 C17 118.66(16) . . ?
O4 C17 C12 115.58(16) . . ?
O4 C17 C16 123.17(17) . . ?
C16 C17 C12 121.25(15) . . ?
C15 C18 C14 105.89(13) 2_655 . ?
C15 C18 C19 105.01(13) 2_655 . ?
C19 C18 C14 105.94(13) . . ?
C19 C19 C18 113.06(9) 2_655 . ?
C20 C19 C18 126.52(16) . . ?
C20 C19 C19 120.42(11) . 2_655 ?
C19 C20 C21 119.02(18) . . ?
C21 C21 C20 120.56(11) 2_655 . ?
N1 C26 C27 166.1(8) . . ?
C28 C27 C26 113.6(5) . . ?
C27 C28 C28 95.8(4) . 2_655 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.380(2) . ?
O1 C22 1.428(3) . ?
O2 C7 1.380(2) . ?
O2 C23 1.416(3) . ?
O3 C10 1.376(2) . ?
O3 C24 1.417(3) . ?
O4 C17 1.369(2) . ?
O4 C25 1.416(3) . ?
C1 C2 1.392(3) . ?
C1 C3 1.393(3) 2_655 ?
C2 C3 1.396(3) . ?
C3 C4 1.524(3) . ?
C4 C5 1.515(3) . ?
C5 C6 1.388(3) . ?
C5 C10 1.395(3) . ?
C6 C7 1.390(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.390(3) . ?
C8 C11 1.518(3) . ?
C9 C10 1.393(3) . ?
C11 C12 1.525(2) . ?
C12 C13 1.397(2) . ?
C12 C17 1.399(3) . ?
C13 C14 1.387(2) . ?
C14 C15 1.395(2) . ?
C14 C18 1.529(2) . ?
C15 C16 1.385(2) . ?
C15 C18 1.525(2) 2_655 ?
C16 C17 1.395(2) . ?
C18 C19 1.526(2) . ?
C19 C19 1.398(3) 2_655 ?
C19 C20 1.382(2) . ?
C20 C21 1.395(3) . ?
C21 C21 1.379(4) 2_655 ?
N1 C26 1.132(7) . ?
C26 C27 1.475(5) . ?
C27 C28 1.466(6) . ?
C28 C28 1.507(9) 2_655 ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.158 818.2 182.0 ?
2 0.500 0.000 -0.529 818.2 182.0 ?
