#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/18/7121877.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_7121877
loop_
_publ_author_name
'Donoshita, Masaki'
'Hayashi, Mikihiro'
'Ikeda, Ryuichi'
'Yoshida, Yukihiro'
'Morikawa, Shota'
'Sugimoto, Kunihisa'
'Kitagawa, Hiroshi'
_publ_section_title
;
 Drastic rearrangement of self-assembled hydrogen-bonded tapes in a
 molecular crystal.
;
_journal_issue                   62
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8571
_journal_page_last               8574
_journal_paper_doi               10.1039/c8cc04376k
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C14 H16 Cl2 N2 O6'
_chemical_formula_sum            'C14 H16 Cl2 N2 O6'
_chemical_formula_weight         379.20
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1zq42x
_audit_update_record
;
2018-04-20 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                103.357(7)
_cell_angle_beta                 96.447(7)
_cell_angle_gamma                93.984(7)
_cell_formula_units_Z            1
_cell_length_a                   4.6904(17)
_cell_length_b                   8.921(3)
_cell_length_c                   9.833(3)
_cell_measurement_reflns_used    2561
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.13
_cell_volume                     395.8(2)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 14.706
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku R-AXIS IV'
_diffrn_measurement_method       ω
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.703010
_diffrn_reflns_av_R_equivalents  0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5200
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.948
_diffrn_reflns_theta_max         27.154
_diffrn_reflns_theta_min         2.124
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             196.00
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0806P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1428
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1422
_reflns_number_total             1799
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c8cc04376k5.cif
_cod_data_source_block           LowB
_cod_depositor_comments
'Adding full bibliography for 7121875--7121878.cif.'
_cod_database_code               7121877
_shelxl_version_number           2014-3
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -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
Cl1 Cl 0.40381(13) 0.24243(6) 0.04031(6) 0.0215(2) Uani 1 1 d
O1 O -0.0426(4) 0.2384(2) -0.19558(18) 0.0222(4) Uani 1 1 d
O2 O 0.4107(4) 0.5526(2) 0.23311(19) 0.0210(4) Uani 1 1 d
O3 O 0.5004(4) 0.8080(2) 0.41721(19) 0.0214(4) Uani 1 1 d
N1 N 0.8116(4) 0.9269(2) 0.6129(2) 0.0178(5) Uani 1 1 d
C1 C -0.0206(5) 0.3555(3) -0.1034(2) 0.0163(5) Uani 1 1 d
C2 C 0.1882(5) 0.3869(3) 0.0226(3) 0.0161(5) Uani 1 1 d
C3 C 0.2171(5) 0.5217(3) 0.1199(3) 0.0173(5) Uani 1 1 d
C4 C 0.7074(5) 0.8081(3) 0.5074(3) 0.0172(5) Uani 1 1 d
C5 C 0.8825(6) 0.6748(3) 0.5140(3) 0.0195(5) Uani 1 1 d
C6 C 1.0674(6) 0.7237(3) 0.6568(3) 0.0207(6) Uani 1 1 d
C7 C 1.0637(6) 0.8996(3) 0.7006(3) 0.0215(6) Uani 1 1 d
H1 H 0.767(6) 1.005(4) 0.624(3) 0.023(8) Uiso 1 1 d
H2 H 0.426(8) 0.652(5) 0.290(4) 0.064(12) Uiso 1 1 d
H3 H 0.755(6) 0.568(3) 0.495(3) 0.020(7) Uiso 1 1 d
H4 H 0.987(6) 0.659(3) 0.437(3) 0.029(8) Uiso 1 1 d
H5 H 1.274(6) 0.696(3) 0.656(3) 0.023(7) Uiso 1 1 d
H6 H 0.980(6) 0.679(3) 0.723(3) 0.028(8) Uiso 1 1 d
H7 H 1.038(6) 0.935(3) 0.803(3) 0.026(7) Uiso 1 1 d
H8 H 1.234(6) 0.948(3) 0.681(3) 0.023(7) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.0000 0.0000
;
International Tables for Crystallography
(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
C3 O2 H2 117(2) .
C4 N1 C7 114.6(2) .
C4 N1 H1 126(2) .
C7 N1 H1 119(2) .
O1 C1 C2 123.8(2) .
O1 C1 C3 118.6(2) 2_565
C2 C1 C3 117.6(2) 2_565
C3 C2 C1 122.3(2) .
C3 C2 Cl1 121.19(19) .
C1 C2 Cl1 116.46(18) .
O2 C3 C2 122.8(2) .
O2 C3 C1 117.2(2) 2_565
C2 C3 C1 120.0(2) 2_565
O3 C4 N1 125.3(2) .
O3 C4 C5 125.8(2) .
N1 C4 C5 108.9(2) .
C4 C5 C6 104.6(2) .
C4 C5 H3 113.1(15) .
C6 C5 H3 115.0(14) .
C4 C5 H4 107.9(18) .
C6 C5 H4 114.5(18) .
H3 C5 H4 102(2) .
C5 C6 C7 104.6(2) .
C5 C6 H5 114.2(16) .
C7 C6 H5 110.1(16) .
C5 C6 H6 109.8(18) .
C7 C6 H6 108.7(19) .
H5 C6 H6 109(2) .
N1 C7 C6 103.1(2) .
N1 C7 H7 109.6(17) .
C6 C7 H7 111.2(17) .
N1 C7 H8 111.5(16) .
C6 C7 H8 109.4(17) .
H7 C7 H8 112(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.720(2) .
O1 C1 1.204(3) .
O2 C3 1.317(3) .
O2 H2 0.93(4) .
O3 C4 1.239(3) .
N1 C4 1.321(3) .
N1 C7 1.452(3) .
N1 H1 0.73(3) .
C1 C2 1.450(3) .
C1 C3 1.505(3) 2_565
C2 C3 1.340(4) .
C3 C1 1.505(3) 2_565
C4 C5 1.500(3) .
C5 C6 1.519(3) .
C5 H3 1.05(3) .
C5 H4 0.94(3) .
C6 C7 1.531(4) .
C6 H5 1.02(3) .
C6 H6 0.96(3) .
C7 H7 1.01(3) .
C7 H8 0.94(3) .
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
O1 C1 C2 C3 176.5(2) . .
C3 C1 C2 C3 -2.6(4) 2_565 .
O1 C1 C2 Cl1 -2.4(3) . .
C3 C1 C2 Cl1 178.50(16) 2_565 .
C1 C2 C3 O2 -178.4(2) . .
Cl1 C2 C3 O2 0.5(4) . .
C1 C2 C3 C1 2.6(4) . 2_565
Cl1 C2 C3 C1 -178.50(17) . 2_565
C7 N1 C4 O3 -177.4(2) . .
C7 N1 C4 C5 2.0(3) . .
O3 C4 C5 C6 -169.5(2) . .
N1 C4 C5 C6 11.1(3) . .
C4 C5 C6 C7 -18.8(3) . .
C4 N1 C7 C6 -14.0(3) . .
C5 C6 C7 N1 19.6(3) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061223
