#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560055.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_1560055
loop_
_publ_author_name
'Rajkumar, Madhu'
'Desiraju, Gautam R.'
_publ_section_title
;
 Quaternary and quinary molecular solids based on structural inequivalence
 and combinatorial approaches: 2-nitroresorcinol and
 4,6-dichlororesorcinol
;
_journal_issue                   2
_journal_name_full               IUCrJ
_journal_page_first              178
_journal_page_last               185
_journal_paper_doi               10.1107/S2052252520016589
_journal_volume                  8
_journal_year                    2021
_chemical_formula_sum            'C40 H46 N8 O8'
_chemical_formula_weight         766.85
_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-2018/3
_cell_angle_alpha                78.729(6)
_cell_angle_beta                 75.782(5)
_cell_angle_gamma                89.099(6)
_cell_formula_units_Z            1
_cell_length_a                   7.5319(7)
_cell_length_b                   8.6425(8)
_cell_length_c                   15.3925(14)
_cell_measurement_reflns_used    9035
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     951.99(15)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.008
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       Block
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0593P)²+0.3903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3565
_reflns_number_total             4348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           15NRES-TMP-DPE-I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1560041--1560072.cif.
;
_cod_database_code               1560055
_shelx_shelxl_version_number     2018/3
_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   0.981
_shelx_estimated_absorpt_t_max   0.981
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
O2 O 0.74232(14) 0.39058(12) 0.11433(7) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.656114 0.354233 0.100021 0.031 Uiso 1 1 calc R U . . .
O4 O 1.09634(15) 0.60447(14) 0.10504(8) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.90113(15) 0.72439(14) 0.28963(8) 0.0291(3) Uani 1 1 d . . . . .
H1 H 0.861090 0.783612 0.324982 0.044 Uiso 1 1 calc R U . . .
O3 O 1.05902(15) 0.42111(14) 0.22552(8) 0.0319(3) Uani 1 1 d . . . . .
N4 N 1.00179(16) 0.52678(14) 0.17525(8) 0.0187(3) Uani 1 1 d . . . . .
N2 N 0.79637(17) 0.90020(14) 0.41860(9) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.70851(17) 1.09154(15) 0.54523(9) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.47151(17) 0.22009(15) 0.08590(9) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.80734(18) 0.56332(16) 0.20322(9) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.7619(2) 0.66648(17) 0.26358(10) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.67929(19) 0.49019(16) 0.17162(9) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.4957(2) 0.52497(18) 0.20210(10) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.405532 0.478685 0.182706 0.026 Uiso 1 1 calc R U . . .
C8 C 0.80473(19) 0.84553(17) 0.50524(10) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.76027(19) 0.94317(18) 0.56908(10) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.15438(19) 0.08327(18) 0.06372(10) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.3473(2) 0.30740(18) 0.05113(10) 0.0232(3) Uani 1 1 d . . . . .
H15 H 0.368715 0.416089 0.034077 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2838(2) -0.00883(18) 0.09885(10) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.266533 -0.117947 0.115558 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5774(2) 0.70031(18) 0.29286(10) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.541560 0.769534 0.332744 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4486(2) 0.62885(18) 0.26140(11) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.325796 0.651604 0.280908 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4379(2) 0.06370(19) 0.10860(10) 0.0236(3) Uani 1 1 d . . . . .
H16 H 0.522913 0.000599 0.132177 0.028 Uiso 1 1 calc R U . . .
C13 C 0.74639(19) 1.04844(17) 0.39377(10) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.70169(19) 1.14479(17) 0.45881(10) 0.0203(3) Uani 1 1 d . . . . .
C18 C 0.1893(2) 0.24508(18) 0.03924(10) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.107141 0.310915 0.015044 0.027 Uiso 1 1 calc R U . . .
C20 C -0.0153(2) 0.01207(19) 0.04939(10) 0.0225(3) Uani 1 1 d . . . . .
H20A H -0.116916 0.081197 0.062692 0.027 Uiso 1 1 calc R U . . .
H20B H -0.046770 -0.088678 0.091195 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7450(2) 1.1043(2) 0.29547(11) 0.0291(4) Uani 1 1 d . . . . .
H14A H 0.791068 1.023800 0.261646 0.044 Uiso 1 1 calc R U . . .
H14B H 0.821061 1.198464 0.270702 0.044 Uiso 1 1 calc R U . . .
H14C H 0.621835 1.126606 0.291093 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6494(2) 1.31371(18) 0.43376(12) 0.0293(4) Uani 1 1 d . . . . .
H11A H 0.599114 1.353313 0.488462 0.044 Uiso 1 1 calc R U . . .
H11B H 0.559710 1.318830 0.398559 0.044 Uiso 1 1 calc R U . . .
H11C H 0.756146 1.376576 0.398295 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8638(2) 0.67898(19) 0.52806(13) 0.0311(4) Uani 1 1 d . . . . .
H7A H 0.759832 0.607622 0.541623 0.047 Uiso 1 1 calc R U . . .
H7B H 0.914717 0.667003 0.580284 0.047 Uiso 1 1 calc R U . . .
H7C H 0.954621 0.655764 0.476880 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7688(2) 0.8892(2) 0.66667(11) 0.0327(4) Uani 1 1 d . . . . .
H10A H 0.742964 0.975651 0.698146 0.049 Uiso 1 1 calc R U . . .
H10B H 0.889008 0.852494 0.668499 0.049 Uiso 1 1 calc R U . . .
H10C H 0.679746 0.804871 0.695820 0.049 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'
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
_geom_angle_publ_flag
C1 O2 H2 109.5 . . ?
C3 O1 H1 109.5 . . ?
O4 N4 O3 124.07(13) . . ?
O4 N4 C2 118.56(12) . . ?
O3 N4 C2 117.36(12) . . ?
C13 N2 C8 119.87(13) . . ?
C12 N3 C9 118.73(13) . . ?
C16 N1 C15 116.70(13) . . ?
C3 C2 C1 123.72(13) . . ?
C3 C2 N4 116.85(12) . . ?
C1 C2 N4 119.38(12) . . ?
O1 C3 C2 116.59(13) . . ?
O1 C3 C4 125.43(13) . . ?
C2 C3 C4 117.97(13) . . ?
O2 C1 C2 117.47(12) . . ?
O2 C1 C6 125.16(13) . . ?
C2 C1 C6 117.37(13) . . ?
C5 C6 C1 119.55(13) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C8 C9 119.78(13) . . ?
N2 C8 C7 117.04(14) . . ?
C9 C8 C7 123.18(14) . . ?
N3 C9 C8 120.93(13) . . ?
N3 C9 C10 116.87(14) . . ?
C8 C9 C10 122.20(14) . . ?
C18 C19 C17 117.45(13) . . ?
C18 C19 C20 120.28(13) . . ?
C17 C19 C20 122.23(13) . . ?
N1 C15 C18 123.69(14) . . ?
N1 C15 H15 118.2 . . ?
C18 C15 H15 118.2 . . ?
C16 C17 C19 119.28(14) . . ?
C16 C17 H17 120.4 . . ?
C19 C17 H17 120.4 . . ?
C5 C4 C3 118.84(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.54(14) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N1 C16 C17 123.52(14) . . ?
N1 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
N2 C13 C12 119.62(13) . . ?
N2 C13 C14 117.43(13) . . ?
C12 C13 C14 122.94(14) . . ?
N3 C12 C13 121.07(13) . . ?
N3 C12 C11 117.26(13) . . ?
C13 C12 C11 121.65(14) . . ?
C15 C18 C19 119.34(14) . . ?
C15 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C19 C20 C20 110.92(15) . 2 ?
C19 C20 H20A 109.5 . . ?
C20 C20 H20A 109.5 2 . ?
C19 C20 H20B 109.5 . . ?
C20 C20 H20B 109.5 2 . ?
H20A C20 H20B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
O2 C1 1.3500(17) . ?
O2 H2 0.8200 . ?
O4 N4 1.2162(16) . ?
O1 C3 1.3465(17) . ?
O1 H1 0.8200 . ?
O3 N4 1.2223(16) . ?
N4 C2 1.4693(18) . ?
N2 C13 1.3391(19) . ?
N2 C8 1.3415(19) . ?
N3 C12 1.3331(19) . ?
N3 C9 1.3423(19) . ?
N1 C16 1.340(2) . ?
N1 C15 1.341(2) . ?
C2 C3 1.390(2) . ?
C2 C1 1.3914(19) . ?
C3 C4 1.397(2) . ?
C1 C6 1.395(2) . ?
C6 C5 1.384(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.394(2) . ?
C8 C7 1.501(2) . ?
C9 C10 1.500(2) . ?
C19 C18 1.387(2) . ?
C19 C17 1.394(2) . ?
C19 C20 1.5090(19) . ?
C15 C18 1.380(2) . ?
C15 H15 0.9300 . ?
C17 C16 1.381(2) . ?
C17 H17 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C13 C12 1.400(2) . ?
C13 C14 1.498(2) . ?
C12 C11 1.507(2) . ?
C18 H18 0.9300 . ?
C20 C20 1.536(3) 2 ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307091
