#------------------------------------------------------------------------------
#$Date: 2020-06-27 04:38:04 +0300 (Sat, 27 Jun 2020) $
#$Revision: 253506 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/07/7240792.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_7240792
loop_
_publ_author_name
'Shimoyama, Daisuke'
'Sekiya, Ryo'
'Maekawa, Hiroyuki'
'Kudo, Hiroto'
'HAINO, Takeharu'
_publ_section_title
;
 One-dimensional arrangement of NORIA in the solid-state
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00650E
_journal_year                    2020
_chemical_formula_moiety
'(C102 H96 O24), 3(C7 H8), 12(C3 H7 N O), 6(C H Cl3), 12(H2 O)'
_chemical_formula_sum            'C165 H234 Cl18 N12 O48'
_chemical_formula_weight         3791.73
_space_group_IT_number           176
_space_group_name_Hall           '-P 6c'
_space_group_name_H-M_alt        'P 63/m'
_symmetry_cell_setting           hexagonal
_symmetry_Int_Tables_number      176
_symmetry_space_group_name_Hall  '-P 6c'
_symmetry_space_group_name_H-M   'P 63/m'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-06-16T13:56:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-06-17 deposited with the CCDC.	2020-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            1
_cell_length_a                   20.144(5)
_cell_length_b                   20.144(5)
_cell_length_c                   25.290(7)
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      18.85
_cell_measurement_theta_min      2.18
_cell_volume                     8887(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bluker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44702
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        18.845
_diffrn_reflns_theta_max         18.844
_diffrn_reflns_theta_min         1.989
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.709
_exptl_crystal_description       block
_exptl_crystal_F_000             1998
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.862
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_gt           0.1692
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5562
_refine_ls_wR_factor_ref         0.6065
_reflns_Friedel_coverage         0
_reflns_number_gt                1554
_reflns_number_total             2416
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00650e2.cif
_cod_data_source_block           platon_sq_CCDC3
_cod_original_cell_volume        8887(5)
_cod_database_code               7240792
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x, y, -z-1/2'
'-y, x-y, -z-1/2'
'-x+y, -x, -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
C1 C 0.8789(8) 0.1727(8) 0.6206(7) 0.115(5) Uani 1 1 d . . . . .
C2 C 0.8392(10) 0.1906(10) 0.6572(8) 0.129(6) Uani 1 1 d . . . . .
C3 C 0.7688(9) 0.1390(8) 0.6758(7) 0.132(6) Uani 1 1 d . . . . .
H3 H 0.743823 0.153914 0.70111 0.159 Uiso 1 1 calc R U . . .
C4 C 0.7339(8) 0.0643(10) 0.6573(7) 0.127(5) Uani 1 1 d . . . . .
C5 C 0.7650(7) 0.0360(8) 0.6205(7) 0.122(6) Uani 1 1 d . . . . .
C6 C 0.8388(7) 0.0971(7) 0.6027(6) 0.118(6) Uani 1 1 d . . . . .
H6 H 0.862777 0.084079 0.57543 0.142 Uiso 1 1 calc R U . . .
C7 C 0.7300(8) -0.0428(6) 0.5995(9) 0.118(6) Uani 1 1 d . . . . .
H7 H 0.688528 -0.075837 0.624946 0.141 Uiso 1 1 calc R U . . .
C8 C 0.6898(10) -0.0490(6) 0.5465(12) 0.108(5) Uani 1 1 d . . . . .
C9 C 0.6106(10) -0.0614(7) 0.5521(12) 0.114(7) Uani 1 1 d . . . . .
C10 C 0.5798(9) -0.0681(6) 0.5024(14) 0.114(7) Uani 1 1 d . . . . .
H10 H 0.527816 -0.080002 0.501738 0.137 Uiso 1 1 calc R U . . .
C11 C 0.6136(9) -0.0600(7) 0.4530(12) 0.110(6) Uani 1 1 d . . . . .
C12 C 0.6914(9) -0.0486(7) 0.4522(13) 0.094(5) Uani 1 1 d . . . . .
C13 C 0.7179(10) -0.0449(7) 0.4977(13) 0.100(6) Uani 1 1 d . . . . .
H13 H 0.768259 -0.037705 0.497653 0.121 Uiso 1 1 calc R U . . .
C14 C 0.7217(8) -0.0473(8) 0.4034(10) 0.121(6) Uani 1 1 d . . . . .
H14 H 0.698655 -0.025589 0.378712 0.145 Uiso 1 1 calc R U . . .
C15 C 0.8149(6) 0.0102(6) 0.3996(7) 0.129(6) Uani 1 1 d . . . . .
H15A H 0.839974 -0.004401 0.427273 0.155 Uiso 1 1 calc R U . . .
H15B H 0.832929 0.002891 0.364853 0.155 Uiso 1 1 calc R U . . .
C16 C 0.8386(6) 0.0897(6) 0.4058(6) 0.119(5) Uani 1 1 d . . . . .
H16A H 0.824258 0.098627 0.441414 0.143 Uiso 1 1 calc R U . . .
H16B H 0.812375 0.104734 0.379266 0.143 Uiso 1 1 calc R U . . .
C17 C 0.9299(5) 0.1409(5) 0.3981(6) 0.122(6) Uani 1 1 d . . . . .
H17A H 0.955897 0.128061 0.426213 0.146 Uiso 1 1 calc R U . . .
H17B H 0.944387 0.128743 0.363598 0.146 Uiso 1 1 calc R U . . .
C301 C 0.2654(7) -0.1551(7) 0.4824(8) 0.156(7) Uani 1 1 d . . . . .
H30A H 0.214508 -0.200772 0.485375 0.234 Uiso 1 1 calc R U . . .
H30B H 0.287236 -0.138091 0.51775 0.234 Uiso 1 1 calc R U . . .
H30C H 0.261048 -0.11411 0.464778 0.234 Uiso 1 1 calc R U . . .
C302 C 0.2778(8) -0.2496(8) 0.4274(8) 0.184(9) Uani 1 1 d . . . . .
H30D H 0.224543 -0.279773 0.439466 0.276 Uiso 1 1 calc R U . . .
H30E H 0.278792 -0.244231 0.388878 0.276 Uiso 1 1 calc R U . . .
H30F H 0.305884 -0.275757 0.437523 0.276 Uiso 1 1 calc R U . . .
C303 C 0.3854(8) -0.1227(7) 0.4419(7) 0.129(6) Uani 1 1 d . . . . .
H303 H 0.404042 -0.071976 0.454565 0.155 Uiso 1 1 calc R U . . .
N301 N 0.3141(6) -0.1731(6) 0.4521(6) 0.125(5) Uani 1 1 d . . . . .
O1 O 0.5779(6) -0.0653(5) 0.4072(6) 0.137(5) Uani 1 1 d . . . . .
H1 H 0.530308 -0.087893 0.412342 0.205 Uiso 1 1 calc R U . . .
O2 O 0.8690(5) 0.2681(4) 0.6729(4) 0.129(4) Uani 1 1 d . . . . .
H2 H 0.871836 0.271096 0.706024 0.194 Uiso 1 1 calc R U . . .
O3 O 0.5733(6) -0.0668(6) 0.5945(7) 0.155(6) Uani 1 1 d . . . . .
H3A H 0.603372 -0.036173 0.617308 0.233 Uiso 1 1 calc R U . . .
O4 O 0.6625(5) 0.0087(5) 0.6753(5) 0.140(4) Uani 1 1 d . . . . .
H4 H 0.646736 0.027778 0.698163 0.21 Uiso 1 1 calc R U . . .
O301 O 0.4309(6) -0.1356(5) 0.4170(6) 0.171(5) Uani 1 1 d . . . . .
C201 C 0.7449(16) -0.2252(10) 0.7472(18) 0.205(7) Uani 0.5 1 d G . P A -1
H201 H 0.73622 -0.27588 0.74396 0.246 Uiso 0.5 1 calc R U P A -1
C202 C 0.6851(13) -0.2132(12) 0.7615(15) 0.205(7) Uani 0.5 1 d G . P A -1
H202 H 0.635533 -0.255675 0.768041 0.246 Uiso 0.5 1 calc R U P A -1
C203 C 0.6978(15) -0.1389(15) 0.7663(13) 0.205(7) Uani 0.5 1 d G . P A -1
H203 H 0.656927 -0.13074 0.776036 0.246 Uiso 0.5 1 calc R U P A -1
C204 C 0.7703(16) -0.0767(10) 0.7567(16) 0.205(7) Uani 0.5 1 d G . P A -1
H204 H 0.779008 -0.026009 0.75995 0.246 Uiso 0.5 1 calc R U P A -1
C205 C 0.8301(13) -0.0887(12) 0.7424(17) 0.205(7) Uani 0.5 1 d G . P A -1
H205 H 0.879695 -0.046213 0.73587 0.246 Uiso 0.5 1 calc R U P A -1
C206 C 0.8174(15) -0.1629(15) 0.7377(18) 0.205(7) Uani 0.5 1 d G . P A -1
C208 C 0.888(2) -0.1774(17) 0.744(3) 0.205(7) Uani 0.5 1 d . . P A -1
H20A H 0.869844 -0.232125 0.739569 0.307 Uiso 0.5 1 calc R U P A -1
H20B H 0.926436 -0.148138 0.716924 0.307 Uiso 0.5 1 calc R U P A -1
H20C H 0.910451 -0.160747 0.779128 0.307 Uiso 0.5 1 calc R U P A -1
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 C1 C6 114.0(14) . . ?
C2 C1 C14 123.1(13) . 8_666 ?
C6 C1 C14 122.3(15) . 8_666 ?
C3 C2 C1 123.5(15) . . ?
C3 C2 O2 116.7(16) . . ?
C1 C2 O2 119.5(15) . . ?
C2 C3 C4 118.9(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
O4 C4 C3 121.7(16) . . ?
O4 C4 C5 112.7(14) . . ?
C3 C4 C5 125.6(14) . . ?
C4 C5 C6 110.0(13) . . ?
C4 C5 C7 127.6(13) . . ?
C6 C5 C7 122.4(14) . . ?
C1 C6 C5 127.9(14) . . ?
C1 C6 H6 116.1 . . ?
C5 C6 H6 116.1 . . ?
C5 C7 C8 110.4(12) . . ?
C5 C7 C17 109.4(13) . 9_546 ?
C8 C7 C17 118.3(14) . 9_546 ?
C5 C7 H7 105.9 . . ?
C8 C7 H7 105.9 . . ?
C17 C7 H7 105.9 9_546 . ?
C13 C8 C9 118.8(19) . . ?
C13 C8 C7 127(2) . . ?
C9 C8 C7 114(2) . . ?
O3 C9 C10 122.5(19) . . ?
O3 C9 C8 129(2) . . ?
C10 C9 C8 109(2) . . ?
C9 C10 C11 130(2) . . ?
C9 C10 H10 115.2 . . ?
C11 C10 H10 115.2 . . ?
O1 C11 C10 123.6(19) . . ?
O1 C11 C12 119(3) . . ?
C10 C11 C12 117(2) . . ?
C13 C12 C14 130.7(18) . . ?
C13 C12 C11 113(2) . . ?
C14 C12 C11 116(2) . . ?
C12 C13 C8 133(2) . . ?
C12 C13 H13 113.4 . . ?
C8 C13 H13 113.4 . . ?
C12 C14 C1 118.8(14) . 9_546 ?
C12 C14 C15 114.0(15) . . ?
C1 C14 C15 105.9(14) 9_546 . ?
C12 C14 H14 105.7 . . ?
C1 C14 H14 105.7 9_546 . ?
C15 C14 H14 105.7 . . ?
C16 C15 C14 114.0(11) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 109.8(9) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C7 C17 C16 111.6(9) 8_666 . ?
C7 C17 H17A 109.3 8_666 . ?
C16 C17 H17A 109.3 . . ?
C7 C17 H17B 109.3 8_666 . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108 . . ?
N301 C301 H30A 109.5 . . ?
N301 C301 H30B 109.5 . . ?
H30A C301 H30B 109.5 . . ?
N301 C301 H30C 109.5 . . ?
H30A C301 H30C 109.5 . . ?
H30B C301 H30C 109.5 . . ?
N301 C302 H30D 109.5 . . ?
N301 C302 H30E 109.5 . . ?
H30D C302 H30E 109.5 . . ?
N301 C302 H30F 109.5 . . ?
H30D C302 H30F 109.5 . . ?
H30E C302 H30F 109.5 . . ?
O301 C303 N301 125.3(13) . . ?
O301 C303 H303 117.4 . . ?
N301 C303 H303 117.4 . . ?
C303 N301 C301 122.6(12) . . ?
C303 N301 C302 120.5(13) . . ?
C301 N301 C302 116.6(11) . . ?
C11 O1 H1 109.5 . . ?
C2 O2 H2 109.5 . . ?
C9 O3 H3A 109.5 . . ?
C4 O4 H4 109.5 . . ?
C202 C201 C206 120 . . ?
C202 C201 H201 120 . . ?
C206 C201 H201 120 . . ?
C201 C202 C203 120 . . ?
C201 C202 H202 120 . . ?
C203 C202 H202 120 . . ?
C204 C203 C202 120 . . ?
C204 C203 H203 120 . . ?
C202 C203 H203 120 . . ?
C205 C204 C203 120 . . ?
C205 C204 H204 120 . . ?
C203 C204 H204 120 . . ?
C204 C205 C206 120 . . ?
C204 C205 H205 120 . . ?
C206 C205 H205 120 . . ?
C205 C206 C201 120 . . ?
C205 C206 C208 119(2) . . ?
C201 C206 C208 117(2) . . ?
C206 C208 H20A 109.5 . . ?
C206 C208 H20B 109.5 . . ?
H20A C208 H20B 109.5 . . ?
C206 C208 H20C 109.5 . . ?
H20A C208 H20C 109.5 . . ?
H20B C208 H20C 109.5 . . ?
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
C1 C2 1.384(18) . ?
C1 C6 1.396(16) . ?
C1 C14 1.49(2) 8_666 ?
C2 C3 1.356(18) . ?
C2 O2 1.421(17) . ?
C3 C4 1.387(18) . ?
C3 H3 0.95 . ?
C4 O4 1.384(14) . ?
C4 C5 1.393(18) . ?
C5 C6 1.449(17) . ?
C5 C7 1.476(17) . ?
C6 H6 0.95 . ?
C7 C8 1.54(2) . ?
C7 C17 1.539(17) 9_546 ?
C7 H7 1 . ?
C8 C13 1.34(2) . ?
C8 C9 1.49(3) . ?
C9 O3 1.28(2) . ?
C9 C10 1.38(2) . ?
C10 C11 1.39(2) . ?
C10 H10 0.95 . ?
C11 O1 1.34(2) . ?
C11 C12 1.47(2) . ?
C12 C13 1.26(2) . ?
C12 C14 1.37(2) . ?
C13 H13 0.95 . ?
C14 C15 1.644(18) . ?
C14 H14 1 . ?
C15 C16 1.432(15) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 C17 1.608(15) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C301 N301 1.426(16) . ?
C301 H30A 0.98 . ?
C301 H30B 0.98 . ?
C301 H30C 0.98 . ?
C302 N301 1.475(16) . ?
C302 H30D 0.98 . ?
C302 H30E 0.98 . ?
C302 H30F 0.98 . ?
C303 O301 1.242(17) . ?
C303 N301 1.304(14) . ?
C303 H303 0.95 . ?
O1 H1 0.84 . ?
O2 H2 0.84 . ?
O3 H3A 0.84 . ?
O4 H4 0.84 . ?
C201 C202 1.39 . ?
C201 C206 1.39 . ?
C201 H201 0.95 . ?
C202 C203 1.39 . ?
C202 H202 0.95 . ?
C203 C204 1.39 . ?
C203 H203 0.95 . ?
C204 C205 1.39 . ?
C204 H204 0.95 . ?
C205 C206 1.39 . ?
C205 H205 0.95 . ?
C206 C208 1.59(3) . ?
C208 H20A 0.98 . ?
C208 H20B 0.98 . ?
C208 H20C 0.98 . ?
