#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:35:42 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/82/7058274.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_7058274
loop_
_publ_author_name
'Liu, Jin-jian'
'Li, Jing'
'Zhao, Guo-zheng'
_publ_section_title
;
 Photochromism of supramolecular assemblies based on benzenecarboxylate
 donors and viologen acceptors
;
_journal_issue                   17
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6607
_journal_paper_doi               10.1039/C9NJ00796B
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C8 H11 N, C10 H4 O8, H2 O'
_chemical_formula_sum            'C18 H17 N O9'
_chemical_formula_weight         391.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-25 deposited with the CCDC.    2019-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                94.996(2)
_cell_angle_beta                 97.741(2)
_cell_angle_gamma                95.460(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4575(6)
_cell_length_b                   9.6725(6)
_cell_length_c                   9.7995(7)
_cell_measurement_reflns_used    8867
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.81
_cell_volume                     879.69(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker D8 venture'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12180
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_min         2.839
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_correction_T_min  0.9418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0626P)²+0.3975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3846
_reflns_number_total             4289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj00796b2.cif
_cod_data_source_block           a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7058273--7058276.cif.'
_cod_database_code               7058274
_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_max   0.965
_shelx_estimated_absorpt_t_min   0.942
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C2'-C3
 1.53 with sigma of 0.001
 C1-C2 = C2-C3 = C1'-C2'
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C2) = Uanis(C2')
Uanis(C1) = Uanis(C1')
4. Others
 Sof(C1')=Sof(H1'a)=Sof(H1'b)=Sof(H1'c)=Sof(C2')=Sof(H2'a)=Sof(H2'b)=Sof(H3bc)=
 Sof(H3bd)=1-FVAR(1)
 Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(H1c)=Sof(C2)=Sof(H2a)=Sof(H2b)=Sof(H3aa)=
 Sof(H3ab)=FVAR(1)
5.a Riding coordinates:
 C3(H3aa,H3ab,H3bc,H3bd)
5.b Free rotating group:
 O9(H9a,H9b)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C2'(H2'a,H2'b)
5.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C18(H18)
5.e Tetrahedral OH refined with riding coordinates:
 O5(H5a), O7(H7a)
5.f Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C1'(H1'a,H1'b,H1'c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.30819(15) 0.73584(15) 0.60721(14) 0.0389(3) Uani 1 1 d . . . . .
O1 O 0.16720(14) 1.06607(11) 0.23472(16) 0.0499(3) Uani 1 1 d . . . . .
O2 O -0.06029(14) 1.01304(13) 0.1531(2) 0.0634(4) Uani 1 1 d . . . . .
O3 O -0.23798(12) 0.81636(13) 0.11368(16) 0.0495(3) Uani 1 1 d . . . . .
O4 O -0.25302(11) 0.59481(12) 0.14599(15) 0.0439(3) Uani 1 1 d . . . . .
O5 O 0.11337(12) 0.31188(11) 0.16641(14) 0.0424(3) Uani 1 1 d . . . . .
H5A H 0.1406 0.2358 0.1810 0.064 Uiso 1 1 calc R . . . .
O6 O 0.32246(12) 0.39292(12) 0.29389(15) 0.0454(3) Uani 1 1 d . . . . .
O7 O 0.47451(11) 0.59246(13) 0.13847(13) 0.0428(3) Uani 1 1 d . . . . .
H7A H 0.5614 0.5887 0.1531 0.064 Uiso 1 1 calc R . . . .
O8 O 0.51141(13) 0.71331(17) 0.34641(15) 0.0557(4) Uani 1 1 d . . . . .
O9 O 0.77556(17) 0.87538(17) 0.46459(18) 0.0640(4) Uani 1 1 d . . . . .
H9A H 0.6981 0.8264 0.4279 0.096 Uiso 1 1 d G . . . .
H9B H 0.7668 0.8895 0.5497 0.096 Uiso 1 1 d G . . . .
C1 C 0.4079(11) 0.8027(6) 0.8993(8) 0.091(2) Uani 0.635(4) 1 d D U P A 1
H1A H 0.3132 0.7538 0.8781 0.137 Uiso 0.635(4) 1 calc GR . P A 1
H1B H 0.4197 0.8517 0.9903 0.137 Uiso 0.635(4) 1 calc GR . P A 1
H1C H 0.4778 0.7372 0.8960 0.137 Uiso 0.635(4) 1 calc GR . P A 1
C2 C 0.4286(4) 0.9063(3) 0.7943(3) 0.0545(7) Uani 0.635(4) 1 d D U P A 1
H2A H 0.3485 0.9621 0.7861 0.065 Uiso 0.635(4) 1 calc R . P A 1
H2B H 0.5156 0.9686 0.8259 0.065 Uiso 0.635(4) 1 calc R . P A 1
C1' C 0.3759(17) 0.8566(15) 0.9134(15) 0.091(2) Uani 0.365(4) 1 d D . P A 2
H1'A H 0.3507 0.9496 0.9048 0.137 Uiso 0.365(4) 1 calc GR . P A 2
H1'B H 0.4188 0.8498 1.0068 0.137 Uiso 0.365(4) 1 calc GR . P A 2
H1'C H 0.2911 0.7913 0.8908 0.137 Uiso 0.365(4) 1 calc GR . P A 2
C2' C 0.4825(6) 0.8233(6) 0.8145(3) 0.0545(7) Uani 0.365(4) 1 d D . P A 2
H2'A H 0.5054 0.7287 0.8245 0.065 Uiso 0.365(4) 1 calc R . P A 2
H2'B H 0.5703 0.8849 0.8449 0.065 Uiso 0.365(4) 1 calc R . P A 2
C3 C 0.4385(2) 0.8350(2) 0.6599(2) 0.0499(4) Uani 1 1 d D . . . .
H3AA H 0.5224 0.7841 0.6671 0.060 Uiso 0.635(4) 1 d R . P A 1
H3AB H 0.4505 0.9034 0.5944 0.060 Uiso 0.635(4) 1 d R . P A 1
H3BC H 0.4186 0.9296 0.6459 0.060 Uiso 0.365(4) 1 d R . P A 2
H3BD H 0.5163 0.8132 0.6093 0.060 Uiso 0.365(4) 1 d R . P A 2
C4 C 0.1803(2) 0.78408(19) 0.5748(2) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.1745 0.8798 0.5813 0.055 Uiso 1 1 calc R . . . .
C5 C 0.31856(18) 0.59806(18) 0.59862(18) 0.0414(4) Uani 1 1 d . . . . .
H5 H 0.4076 0.5659 0.6205 0.050 Uiso 1 1 calc R . . . .
C6 C 0.19934(18) 0.50436(18) 0.55801(17) 0.0400(4) Uani 1 1 d . . . . .
H6 H 0.2080 0.4092 0.5535 0.048 Uiso 1 1 calc R . . . .
C7 C 0.05857(18) 0.69403(18) 0.53247(19) 0.0424(4) Uani 1 1 d . . . . .
H7 H -0.0289 0.7290 0.5097 0.051 Uiso 1 1 calc R . . . .
C8 C 0.06513(16) 0.55016(16) 0.52337(14) 0.0334(3) Uani 1 1 d . . . . .
C9 C -0.18041(14) 0.70610(15) 0.14105(15) 0.0288(3) Uani 1 1 d . . . . .
C10 C -0.01834(13) 0.70811(13) 0.16904(13) 0.0227(2) Uani 1 1 d . . . . .
C11 C 0.08616(14) 0.82497(13) 0.19423(14) 0.0252(3) Uani 1 1 d . . . . .
C12 C 0.06164(17) 0.97823(14) 0.19413(17) 0.0350(3) Uani 1 1 d . . . . .
C13 C 0.23056(14) 0.80180(13) 0.22235(15) 0.0279(3) Uani 1 1 d . . . . .
H13 H 0.2998 0.8786 0.2406 0.033 Uiso 1 1 calc R . . . .
C14 C 0.27472(13) 0.66966(13) 0.22413(14) 0.0244(3) Uani 1 1 d . . . . .
C15 C 0.43392(14) 0.65886(14) 0.24421(16) 0.0300(3) Uani 1 1 d . . . . .
C16 C 0.17142(13) 0.55402(12) 0.20134(13) 0.0222(2) Uani 1 1 d . . . . .
C17 C 0.21229(14) 0.41099(13) 0.22307(14) 0.0263(3) Uani 1 1 d . . . . .
C18 C 0.02766(13) 0.57517(13) 0.17354(13) 0.0225(2) Uani 1 1 d . . . . .
H18 H -0.0409 0.4978 0.1573 0.027 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 0.0033 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_3
C4 N1 C3 120.20(15) .
C5 N1 C3 119.30(14) .
C5 N1 C4 120.42(15) .
C3 C2 C1 111.0(3) .
C1' C2' C3 118.2(8) .
N1 C3 C2' 109.4(2) .
C2 C3 N1 111.71(18) .
N1 C4 C7 120.84(16) .
N1 C5 C6 120.64(15) .
C5 C6 C8 120.65(15) .
C4 C7 C8 120.30(15) .
C6 C8 C7 117.13(15) .
C6 C8 C8 121.37(17) 2_566
C7 C8 C8 121.49(17) 2_566
O3 C9 C10 120.79(12) .
O4 C9 O3 121.72(13) .
O4 C9 C10 117.48(12) .
C11 C10 C9 128.16(11) .
C18 C10 C9 113.48(11) .
C18 C10 C11 118.32(11) .
C10 C11 C12 127.54(12) .
C13 C11 C10 118.25(11) .
C13 C11 C12 114.21(11) .
O1 C12 O2 122.06(13) .
O1 C12 C11 117.22(13) .
O2 C12 C11 120.71(13) .
C14 C13 C11 122.82(12) .
C13 C14 C15 117.45(11) .
C13 C14 C16 119.00(11) .
C16 C14 C15 123.48(11) .
O7 C15 C14 112.28(12) .
O8 C15 O7 125.94(13) .
O8 C15 C14 121.70(13) .
C14 C16 C17 120.79(11) .
C18 C16 C14 118.88(11) .
C18 C16 C17 119.92(11) .
O5 C17 C16 113.09(11) .
O6 C17 O5 124.79(12) .
O6 C17 C16 121.96(12) .
C16 C18 C10 122.69(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C3 1.491(2) .
N1 C4 1.346(2) .
N1 C5 1.342(2) .
O1 C12 1.2448(19) .
O2 C12 1.256(2) .
O3 C9 1.2755(17) .
O4 C9 1.2288(18) .
O5 C17 1.3035(17) .
O6 C17 1.2078(17) .
O7 C15 1.2929(19) .
O8 C15 1.2060(19) .
C1 C2 1.515(7) .
C2 C3 1.451(4) .
C1' C2' 1.527(9) .
C2' C3 1.5331(10) .
C4 C7 1.369(3) .
C5 C6 1.368(3) .
C6 C8 1.393(2) .
C7 C8 1.394(2) .
C8 C8 1.487(3) 2_566
C9 C10 1.5183(17) .
C10 C11 1.4102(17) .
C10 C18 1.3985(17) .
C11 C12 1.5221(18) .
C11 C13 1.3996(18) .
C13 C14 1.3827(18) .
C14 C15 1.5067(17) .
C14 C16 1.3947(17) .
C16 C17 1.4965(17) .
C16 C18 1.3884(16) .
