#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:53:29 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257451 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/97/7239708.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_7239708
loop_
_publ_author_name
'Baig, Fayaz'
'Rangan, Krishnan'
'Eappen, Shibu M.'
'Mandal, Sanjay K.'
'Sarkar, Madhushree'
_publ_section_title
;
 Template effect of innocent and coordinating anions on the formation of
 interpenetrated 2D and 3D networks: methyl orange and iodine sorption
 studies
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              751
_journal_page_last               766
_journal_paper_doi               10.1039/C9CE00998A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '0.5(C28 H30 N8), Cl O4'
_chemical_formula_sum            'C14 H15 Cl N4 O4'
_chemical_formula_weight         338.75
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc219yz9
_audit_creation_date             2019-10-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-06 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.482(4)
_cell_length_b                   10.5445(13)
_cell_length_c                   11.8015(13)
_cell_measurement_reflns_used    6423
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.9320
_cell_measurement_theta_min      5.0900
_cell_volume                     3171.0(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9600
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.432
_diffrn_reflns_theta_min         2.711
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.78562
_exptl_absorpt_correction_T_min  0.73256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 490 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0887
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2646
_refine_ls_wR_factor_ref         0.2899
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.798
_reflns_number_gt                1353
_reflns_number_total             1818
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00998a2.cif
_cod_data_source_block           l1clo4
_cod_depositor_comments
;Adding full bibliography for 7239708--7239712.cif.

 Adding full bibliography for 7239708--7239712.cif.
;
_cod_database_code               7239708
_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   0.949
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
Cl1 Cl 0.5000 0.0000 0.2997(2) 0.0833(10) Uani 1 2 d S T P
O1 O 0.4854(5) 0.1028(8) 0.2328(9) 0.137(3) Uani 1 1 d . . .
O2 O 0.5319(6) 0.042(2) 0.3814(15) 0.224(7) Uiso 1 1 d . . .
N1 N 0.27293(16) 0.2853(5) 0.4869(5) 0.0572(14) Uani 1 1 d . . .
N2 N 0.45392(19) 0.4387(6) 0.4974(6) 0.0633(15) Uani 1 1 d . . .
H2 H 0.4826 0.4801 0.5076 0.076 Uiso 0.5 1 calc R . .
C1 C 0.36238(19) 0.3094(5) 0.4596(5) 0.0478(12) Uani 1 1 d . . .
C2 C 0.3132(2) 0.2360(5) 0.4423(5) 0.0495(13) Uani 1 1 d . . .
C3 C 0.4085(3) 0.4907(7) 0.5266(9) 0.075(2) Uani 1 1 d . . .
H3 H 0.4082 0.5688 0.5632 0.089 Uiso 1 1 calc R . .
C4 C 0.3609(2) 0.4291(6) 0.5031(6) 0.0591(16) Uani 1 1 d . . .
H4 H 0.3291 0.4692 0.5169 0.071 Uiso 1 1 calc R . .
C5 C 0.4107(2) 0.2569(6) 0.4309(6) 0.0595(16) Uani 1 1 d . . .
H5 H 0.4126 0.1773 0.3974 0.071 Uiso 1 1 calc R . .
C6 C 0.4554(2) 0.3254(7) 0.4532(7) 0.0651(17) Uani 1 1 d . . .
H6 H 0.4879 0.2896 0.4362 0.078 Uiso 1 1 calc R . .
C7 C 0.3139(3) 0.1131(7) 0.3802(8) 0.076(2) Uani 1 1 d . . .
H7A H 0.3410 0.0598 0.4106 0.115 Uiso 1 1 calc GR . .
H7B H 0.3206 0.1285 0.3013 0.115 Uiso 1 1 calc GR . .
H7C H 0.2805 0.0719 0.3886 0.115 Uiso 1 1 calc GR . .
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'
Cl Cl 0.1484 0.1585 '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_1
_geom_angle_site_symmetry_3
O1 Cl1 O1 110.9(9) 2_655 .
O2 Cl1 O1 108.1(11) . .
O2 Cl1 O1 108.1(11) 2_655 2_655
O2 Cl1 O1 120.4(10) . 2_655
O2 Cl1 O1 120.4(10) 2_655 .
O2 Cl1 O2 87.8(15) . 2_655
C2 N1 N1 117.6(6) . 14
C3 N2 H2 119.7 . .
C6 N2 H2 119.7 . .
C6 N2 C3 120.6(5) . .
C4 C1 C2 120.7(5) . .
C4 C1 C5 118.9(5) . .
C5 C1 C2 120.3(5) . .
N1 C2 C1 114.4(5) . .
N1 C2 C7 124.8(5) . .
C1 C2 C7 120.7(5) . .
N2 C3 H3 119.6 . .
N2 C3 C4 120.8(7) . .
C4 C3 H3 119.6 . .
C1 C4 C3 118.6(6) . .
C1 C4 H4 120.7 . .
C3 C4 H4 120.7 . .
C1 C5 H5 120.7 . .
C6 C5 C1 118.6(6) . .
C6 C5 H5 120.7 . .
N2 C6 C5 122.2(6) . .
N2 C6 H6 118.9 . .
C5 C6 H6 118.9 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 O1 1.392(8) 2_655
Cl1 O1 1.392(8) .
Cl1 O2 1.338(17) .
Cl1 O2 1.338(17) 2_655
N1 N1 1.386(8) 14
N1 C2 1.266(8) .
N2 H2 0.8600 .
N2 C3 1.325(9) .
N2 C6 1.304(10) .
C1 C2 1.486(6) .
C1 C4 1.363(8) .
C1 C5 1.391(8) .
C2 C7 1.489(9) .
C3 H3 0.9300 .
C3 C4 1.403(7) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C5 C6 1.375(8) .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N2 0.86 1.83 2.681(9) 167.8 2_665
C5 H5 O2 0.93 2.72 3.53(3) 145.8 2_655
C7 H7B O2 0.96 2.39 3.21(2) 143.2 12_454
C7 H7C O1 0.96 2.60 3.252(11) 125.8 15_545
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
N1 N1 C2 C1 -171.9(4) 14
N1 N1 C2 C7 6.1(10) 14
N2 C3 C4 C1 6.3(13) .
C1 C5 C6 N2 -1.9(12) .
C2 C1 C4 C3 174.8(8) .
C2 C1 C5 C6 -176.9(6) .
C3 N2 C6 C5 2.6(12) .
C4 C1 C2 N1 -10.5(9) .
C4 C1 C2 C7 171.3(7) .
C4 C1 C5 C6 3.4(11) .
C5 C1 C2 N1 169.9(6) .
C5 C1 C2 C7 -8.3(10) .
C5 C1 C4 C3 -5.6(11) .
C6 N2 C3 C4 -4.8(13) .
