#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560046.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_1560046
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            'C26 H21 N5 O4'
_chemical_formula_weight         467.48
_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                105.915(7)
_cell_angle_beta                 102.665(7)
_cell_angle_gamma                91.242(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3217(8)
_cell_length_b                   11.6513(13)
_cell_length_c                   13.9987(16)
_cell_measurement_reflns_used    10398
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.1
_cell_volume                     1116.2(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.113
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       Block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0397
_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)+(0.0504P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4075
_reflns_number_total             5120
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           6NRES-33BP
_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               1560046
_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 0.62535(13) -0.01397(8) 0.37342(7) 0.0223(2) Uani 1 1 d . . . . .
H2 H 0.641170 0.054860 0.370726 0.033 Uiso 1 1 calc R U . . .
O1 O 0.93638(13) -0.34882(8) 0.41651(7) 0.0224(2) Uani 1 1 d . . . . .
H1 H 1.020157 -0.388530 0.398165 0.034 Uiso 1 1 calc R U . . .
O4 O 0.51596(14) -0.30008(10) 0.32253(8) 0.0337(3) Uani 1 1 d . . . . .
O3 O 0.58962(15) -0.22002(11) 0.48531(8) 0.0372(3) Uani 1 1 d . . . . .
N2 N 0.65425(16) 0.19231(10) 0.32435(9) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.62009(15) -0.23644(10) 0.40083(8) 0.0187(2) Uani 1 1 d . . . . .
N3 N 0.77484(17) 0.01404(11) -0.07001(9) 0.0284(3) Uani 1 1 d . . . . .
N4 N 0.15102(16) 0.48877(10) 0.33818(8) 0.0217(2) Uani 1 1 d . . . . .
C7 C 0.65747(19) 0.31084(12) 0.36573(10) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.652692 0.339692 0.433927 0.027 Uiso 1 1 calc R U . . .
N5 N 0.26793(17) 0.47096(11) -0.05175(9) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.95337(18) -0.24026(11) 0.40054(9) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.95771(19) -0.01179(12) 0.37179(9) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.961842 0.063836 0.361827 0.024 Uiso 1 1 calc R U . . .
C8 C 0.66768(19) 0.39178(12) 0.31041(10) 0.0225(3) Uani 1 1 d . . . . .
H8 H 0.668643 0.473514 0.340960 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2032(2) 0.37109(13) -0.12776(10) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.209181 0.370682 -0.193531 0.031 Uiso 1 1 calc R U . . .
C6 C 0.78975(18) -0.06454(12) 0.37842(9) 0.0175(3) Uani 1 1 d . . . . .
C3 C 1.11915(18) -0.18578(12) 0.39408(10) 0.0208(3) Uani 1 1 d . . . . .
H3 H 1.228918 -0.224685 0.399055 0.025 Uiso 1 1 calc R U . . .
C17 C 0.16363(19) 0.38823(13) 0.36748(10) 0.0230(3) Uani 1 1 d . . . . .
H17 H 0.158415 0.392356 0.434112 0.028 Uiso 1 1 calc R U . . .
C22 C 0.18462(18) 0.37099(12) 0.06467(9) 0.0184(3) Uani 1 1 d . . . . .
C23 C 0.11819(19) 0.26859(13) -0.01687(10) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.067616 0.200779 -0.005805 0.028 Uiso 1 1 calc R U . . .
C18 C 0.18402(19) 0.27911(12) 0.30256(10) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.193401 0.211312 0.325595 0.027 Uiso 1 1 calc R U . . .
C20 C 0.17866(17) 0.37416(12) 0.17056(9) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.68266(18) 0.17468(12) 0.05662(10) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.60805(19) 0.22874(13) -0.01910(10) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.553323 0.300652 -0.002637 0.027 Uiso 1 1 calc R U . . .
C1 C 0.79311(17) -0.17821(11) 0.39235(9) 0.0156(3) Uani 1 1 d . . . . .
C21 C 0.15935(18) 0.48038(12) 0.24181(10) 0.0197(3) Uani 1 1 d . . . . .
H21 H 0.151736 0.549902 0.221242 0.024 Uiso 1 1 calc R U . . .
C10 C 0.67462(17) 0.22681(12) 0.16446(10) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.19042(18) 0.27104(12) 0.20308(10) 0.0200(3) Uani 1 1 d . . . . .
H19 H 0.202443 0.197684 0.158289 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6994(2) 0.06804(13) -0.14041(11) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.703288 0.031777 -0.207885 0.034 Uiso 1 1 calc R U . . .
C11 C 0.66194(18) 0.15294(12) 0.22636(10) 0.0207(3) Uani 1 1 d . . . . .
H11 H 0.658610 0.070671 0.197519 0.025 Uiso 1 1 calc R U . . .
C26 C 0.25837(19) 0.46885(12) 0.04215(10) 0.0229(3) Uani 1 1 d . . . . .
H26 H 0.304092 0.537377 0.095948 0.027 Uiso 1 1 calc R U . . .
C4 C 1.11832(18) -0.07265(13) 0.38011(9) 0.0214(3) Uani 1 1 d . . . . .
H4 H 1.229586 -0.036173 0.376162 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6164(2) 0.17415(14) -0.11897(11) 0.0277(3) Uani 1 1 d . . . . .
H15 H 0.566857 0.208459 -0.170666 0.033 Uiso 1 1 calc R U . . .
C9 C 0.67644(18) 0.34953(12) 0.20903(10) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.683489 0.402817 0.170933 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1283(2) 0.26893(13) -0.11444(10) 0.0263(3) Uani 1 1 d . . . . .
H24 H 0.085367 0.201493 -0.169766 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7658(2) 0.06833(12) 0.02637(11) 0.0241(3) Uani 1 1 d . . . . .
H13 H 0.818620 0.032535 0.076518 0.029 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
C11 N2 C7 117.82(11) . . ?
O3 N1 O4 123.75(12) . . ?
O3 N1 C1 118.21(11) . . ?
O4 N1 C1 118.02(10) . . ?
C16 N3 C13 116.48(12) . . ?
C21 N4 C17 117.55(11) . . ?
N2 C7 C8 122.26(13) . . ?
C25 N5 C26 116.79(12) . . ?
O1 C2 C3 124.80(12) . . ?
O1 C2 C1 117.02(11) . . ?
C3 C2 C1 118.17(12) . . ?
C4 C5 C6 119.68(12) . . ?
C7 C8 C9 119.20(13) . . ?
N5 C25 C24 123.86(12) . . ?
O2 C6 C1 117.43(11) . . ?
O2 C6 C5 125.41(12) . . ?
C1 C6 C5 117.15(12) . . ?
C4 C3 C2 118.95(12) . . ?
N4 C17 C18 122.47(12) . . ?
C26 C22 C23 117.01(12) . . ?
C26 C22 C20 121.78(12) . . ?
C23 C22 C20 121.20(12) . . ?
C24 C23 C22 119.35(13) . . ?
C17 C18 C19 119.59(12) . . ?
C21 C20 C19 117.00(12) . . ?
C21 C20 C22 121.34(12) . . ?
C19 C20 C22 121.66(12) . . ?
C13 C12 C14 117.02(12) . . ?
C13 C12 C10 120.95(12) . . ?
C14 C12 C10 122.03(12) . . ?
C15 C14 C12 119.25(13) . . ?
C6 C1 C2 123.66(12) . . ?
C6 C1 N1 118.95(11) . . ?
C2 C1 N1 117.38(11) . . ?
N4 C21 C20 124.14(12) . . ?
C9 C10 C11 116.65(12) . . ?
C9 C10 C12 122.89(12) . . ?
C11 C10 C12 120.45(12) . . ?
C18 C19 C20 119.24(12) . . ?
N3 C16 C15 123.93(13) . . ?
N2 C11 C10 124.43(12) . . ?
N5 C26 C22 124.39(13) . . ?
C3 C4 C5 122.39(12) . . ?
C16 C15 C14 118.77(13) . . ?
C8 C9 C10 119.64(12) . . ?
C25 C24 C23 118.59(13) . . ?
N3 C13 C12 124.55(13) . . ?
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 C6 1.3481(15) . ?
O1 C2 1.3512(15) . ?
O4 N1 1.2231(15) . ?
O3 N1 1.2159(14) . ?
N2 C11 1.3361(17) . ?
N2 C7 1.3406(18) . ?
N1 C1 1.4669(16) . ?
N3 C16 1.3373(19) . ?
N3 C13 1.3408(18) . ?
N4 C21 1.3405(16) . ?
N4 C17 1.3419(17) . ?
C7 C8 1.3847(19) . ?
N5 C25 1.3367(19) . ?
N5 C26 1.3383(17) . ?
C2 C3 1.3895(18) . ?
C2 C1 1.3913(17) . ?
C5 C4 1.3859(19) . ?
C5 C6 1.3954(18) . ?
C8 C9 1.3851(19) . ?
C25 C24 1.375(2) . ?
C6 C1 1.3905(18) . ?
C3 C4 1.384(2) . ?
C17 C18 1.378(2) . ?
C22 C26 1.3914(19) . ?
C22 C23 1.3955(19) . ?
C22 C20 1.4829(17) . ?
C23 C24 1.3850(19) . ?
C18 C19 1.3811(18) . ?
C20 C21 1.3925(18) . ?
C20 C19 1.3949(18) . ?
C12 C13 1.3940(19) . ?
C12 C14 1.3949(18) . ?
C12 C10 1.4796(18) . ?
C14 C15 1.384(2) . ?
C10 C9 1.3929(19) . ?
C10 C11 1.3932(18) . ?
C16 C15 1.377(2) . ?
