#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:34:20 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226917 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/54/4035462.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_4035462
loop_
_publ_author_name
'Mao, Weipeng'
'Zhan, Shuaijun'
'Zhu, Bowei'
'Ma, Da'
_publ_section_title
;
 Step-Growth Cyclo-Oligomerization for the Preparation of Di- and
 Tetrafunctionalized Pillar[5]arenes.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4147
_journal_page_last               4152
_journal_paper_doi               10.1021/acs.joc.8b00073
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C26 H30 O6'
_chemical_formula_weight         438.50
_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                104.552(13)
_cell_angle_beta                 105.653(14)
_cell_angle_gamma                109.975(9)
_cell_formula_units_Z            1
_cell_length_a                   7.765(5)
_cell_length_b                   8.873(6)
_cell_length_c                   9.701(10)
_cell_measurement_reflns_used    1689
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.64
_cell_volume                     559.6(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4100
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.357
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             234
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.069(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00073_si_003.cif
_cod_data_source_block           mo_60627aa
_cod_database_code               4035462
_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. 
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.982
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 0.51335(16) 0.56321(15) 0.23714(12) 0.0462(3) Uani 1 1 d . .
O2 O 0.18943(18) 0.76099(14) 0.54026(13) 0.0498(3) Uani 1 1 d . .
O3 O 0.2597(3) 0.94421(17) 0.04829(14) 0.0765(5) Uani 1 1 d . .
C1 C 0.6714(2) 0.52609(17) 0.47307(16) 0.0366(3) Uani 1 1 d . .
H1 H 0.7865 0.5439 0.4541 0.044 Uiso 1 1 calc R U
C2 C 0.5129(2) 0.53393(16) 0.36986(15) 0.0349(3) Uani 1 1 d . .
C3 C 0.33944(19) 0.50764(16) 0.39719(15) 0.0339(3) Uani 1 1 d . .
C4 C 0.1653(2) 0.51558(17) 0.28614(17) 0.0379(4) Uani 1 1 d . .
H4A H 0.1368 0.4441 0.1815 0.045 Uiso 1 1 calc R U
H4B H 0.0488 0.4665 0.3086 0.045 Uiso 1 1 calc R U
C5 C 0.20024(19) 0.69701(17) 0.29345(16) 0.0348(3) Uani 1 1 d . .
C6 C 0.2142(2) 0.81879(18) 0.42462(17) 0.0371(4) Uani 1 1 d . .
C7 C 0.2475(2) 0.98465(19) 0.43149(18) 0.0445(4) Uani 1 1 d . .
H7 H 0.2593 1.0655 0.5201 0.053 Uiso 1 1 calc R U
C8 C 0.2635(3) 1.0316(2) 0.30847(19) 0.0472(4) Uani 1 1 d . .
H8 H 0.2859 1.1433 0.3141 0.057 Uiso 1 1 calc R U
C9 C 0.2458(3) 0.9115(2) 0.17739(17) 0.0465(4) Uani 1 1 d . .
C10 C 0.2152(2) 0.74509(18) 0.17160(17) 0.0418(4) Uani 1 1 d . .
H10 H 0.2046 0.6649 0.0831 0.050 Uiso 1 1 calc R U
C11 C 0.6885(3) 0.5960(3) 0.2078(2) 0.0562(5) Uani 1 1 d . .
H11A H 0.7983 0.6943 0.2932 0.084 Uiso 1 1 calc R U
H11B H 0.6713 0.6196 0.1150 0.084 Uiso 1 1 calc R U
H11C H 0.7149 0.4964 0.1954 0.084 Uiso 1 1 calc R U
C12 C 0.2115(3) 0.8835(2) 0.6772(2) 0.0593(5) Uani 1 1 d . .
H12A H 0.3359 0.9843 0.7150 0.089 Uiso 1 1 calc R U
H12B H 0.2096 0.8334 0.7541 0.089 Uiso 1 1 calc R U
H12C H 0.1041 0.9158 0.6556 0.089 Uiso 1 1 calc R U
C13 C 0.3029(6) 1.1162(3) 0.0567(3) 0.1109(12) Uani 1 1 d . U
H13A H 0.2000 1.1449 0.0739 0.166 Uiso 1 1 calc R U
H13B H 0.3097 1.1246 -0.0386 0.166 Uiso 1 1 calc R U
H13C H 0.4284 1.1953 0.1406 0.166 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'
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
C2 O1 C11 117.94(12) .
C6 O2 C12 116.98(14) .
C9 O3 C13 116.45(14) .
C3 C1 C2 121.33(13) 2_666
O1 C2 C3 116.20(12) .
O1 C2 C1 123.92(13) .
C3 C2 C1 119.87(14) .
C1 C3 C2 118.80(12) 2_666
C1 C3 C4 120.57(13) 2_666
C2 C3 C4 120.63(14) .
C5 C4 C3 114.22(11) .
C10 C5 C6 118.29(14) .
C10 C5 C4 121.39(12) .
C6 C5 C4 120.30(13) .
O2 C6 C7 124.07(13) .
O2 C6 C5 115.72(13) .
C7 C6 C5 120.20(14) .
C8 C7 C6 120.89(14) .
C9 C8 C7 119.37(15) .
C8 C9 O3 124.30(14) .
C8 C9 C10 119.64(15) .
O3 C9 C10 116.05(13) .
C5 C10 C9 121.59(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.377(2) .
O1 C11 1.412(2) .
O2 C6 1.377(2) .
O2 C12 1.414(2) .
O3 C9 1.378(2) .
O3 C13 1.421(2) .
C1 C3 1.382(2) 2_666
C1 C2 1.397(2) .
C2 C3 1.395(2) .
C3 C1 1.382(2) 2_666
C3 C4 1.5201(19) .
C4 C5 1.518(2) .
C5 C10 1.373(2) .
C5 C6 1.397(2) .
C6 C7 1.385(2) .
C7 C8 1.381(2) .
C8 C9 1.377(2) .
C9 C10 1.397(2) .
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_1
_geom_torsion_site_symmetry_4
C11 O1 C2 C3 177.98(13) . .
C11 O1 C2 C1 -3.4(2) . .
C3 C1 C2 O1 -178.51(11) 2_666 .
C3 C1 C2 C3 0.1(2) 2_666 .
O1 C2 C3 C1 178.62(11) . 2_666
C1 C2 C3 C1 -0.1(2) . 2_666
O1 C2 C3 C4 -1.26(18) . .
C1 C2 C3 C4 -179.97(11) . .
C1 C3 C4 C5 107.60(15) 2_666 .
C2 C3 C4 C5 -72.52(16) . .
C3 C4 C5 C10 112.96(15) . .
C3 C4 C5 C6 -68.27(18) . .
C12 O2 C6 C7 -3.9(2) . .
C12 O2 C6 C5 177.28(13) . .
C10 C5 C6 O2 177.23(11) . .
C4 C5 C6 O2 -1.58(18) . .
C10 C5 C6 C7 -1.7(2) . .
C4 C5 C6 C7 179.54(13) . .
O2 C6 C7 C8 -177.49(13) . .
C5 C6 C7 C8 1.3(2) . .
C6 C7 C8 C9 0.0(2) . .
C7 C8 C9 O3 -179.81(16) . .
C7 C8 C9 C10 -1.0(3) . .
C13 O3 C9 C8 2.6(3) . .
C13 O3 C9 C10 -176.3(2) . .
C6 C5 C10 C9 0.7(2) . .
C4 C5 C10 C9 179.52(13) . .
C8 C9 C10 C5 0.6(2) . .
O3 C9 C10 C5 179.52(14) . .
