#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560048.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_1560048
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            'C18 H17 N3 O4'
_chemical_formula_weight         339.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.187(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.802(3)
_cell_length_b                   7.5355(11)
_cell_length_c                   12.5671(19)
_cell_measurement_reflns_used    13038
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.1
_cell_volume                     1685.5(5)
_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 0.999
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16334
_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         27.483
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       Block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3859
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0736
_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)+(0.0721P)²+1.9128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2673
_reflns_number_total             3859
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           8NRES-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_original_cell_volume        1685.5(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1560048
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.83534(12) 0.1880(3) 0.77910(16) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.860190 0.277402 0.791915 0.050 Uiso 1 1 calc R U . . .
O1 O 0.66069(13) -0.0619(3) 0.53742(17) 0.0393(6) Uani 1 1 d . . . . .
H1 H 0.635883 -0.041637 0.483071 0.059 Uiso 1 1 calc R U . . .
O4 O 0.70962(13) -0.0781(3) 0.80485(17) 0.0406(6) Uani 1 1 d . . . . .
O3 O 0.77914(14) -0.2170(3) 0.6928(2) 0.0478(6) Uani 1 1 d . . . . .
N3 N 0.74516(14) -0.0852(3) 0.72221(19) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.90735(15) 0.4803(3) 0.8462(2) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.58340(14) -0.0297(4) 0.3534(2) 0.0334(6) Uani 1 1 d . . . . .
C6 C 0.79470(15) 0.2120(4) 0.6882(2) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.74767(15) 0.0740(4) 0.6550(2) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.70453(16) 0.0795(4) 0.5608(2) 0.0284(6) Uani 1 1 d . . . . .
C11 C 0.96895(17) 0.7614(4) 0.9644(2) 0.0303(6) Uani 1 1 d . . . . .
C7 C 0.98037(18) 0.5232(4) 0.8398(2) 0.0326(7) Uani 1 1 d . . . . .
H7 H 1.010590 0.456860 0.795306 0.039 Uiso 1 1 calc R U . . .
C5 C 0.79792(16) 0.3626(4) 0.6242(2) 0.0308(6) Uani 1 1 d . . . . .
H5 H 0.827660 0.458504 0.644898 0.037 Uiso 1 1 calc R U . . .
C10 C 1.01236(16) 0.6613(4) 0.8965(2) 0.0312(6) Uani 1 1 d . . . . .
H10 H 1.063061 0.687326 0.889239 0.037 Uiso 1 1 calc R U . . .
C3 C 0.71006(16) 0.2306(4) 0.4967(2) 0.0309(6) Uani 1 1 d . . . . .
H3 H 0.682919 0.238397 0.432811 0.037 Uiso 1 1 calc R U . . .
C4 C 0.75657(17) 0.3687(4) 0.5297(2) 0.0322(7) Uani 1 1 d . . . . .
H4 H 0.760119 0.468862 0.486811 0.039 Uiso 1 1 calc R U . . .
C13 C 0.62871(18) -0.0466(4) 0.2708(2) 0.0348(7) Uani 1 1 d . . . . .
H13 H 0.680331 -0.046144 0.283739 0.042 Uiso 1 1 calc R U . . .
C9 C 0.89352(18) 0.7174(4) 0.9702(3) 0.0376(7) Uani 1 1 d . . . . .
H9 H 0.862006 0.781271 1.014196 0.045 Uiso 1 1 calc R U . . .
C12 C 1.00254(19) 0.9110(4) 1.0297(2) 0.0359(7) Uani 1 1 d . . . . .
H12A H 1.054809 0.884529 1.046306 0.043 Uiso 1 1 calc R U . . .
H12B H 0.976215 0.920443 1.096293 0.043 Uiso 1 1 calc R U . . .
C14 C 0.50914(18) -0.0266(4) 0.3326(3) 0.0375(7) Uani 1 1 d . . . . .
H14 H 0.476569 -0.014994 0.389125 0.045 Uiso 1 1 calc R U . . .
C17 C 0.52625(19) -0.0622(4) 0.1450(3) 0.0381(8) Uani 1 1 d . . . . .
C8 C 0.86558(18) 0.5780(5) 0.9100(3) 0.0405(8) Uani 1 1 d . . . . .
H8 H 0.814754 0.551033 0.914374 0.049 Uiso 1 1 calc R U . . .
C15 C 0.60292(18) -0.0646(5) 0.1674(3) 0.0394(8) Uani 1 1 d . . . . .
H15 H 0.636789 -0.078255 0.112661 0.047 Uiso 1 1 calc R U . . .
C16 C 0.47917(18) -0.0401(4) 0.2306(3) 0.0395(8) Uani 1 1 d . . . . .
H16 H 0.427427 -0.034386 0.219380 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4975(3) -0.0832(5) 0.0314(3) 0.0561(11) Uani 1 1 d . . . . .
H18A H 0.526368 -0.175011 -0.003218 0.067 Uiso 1 1 calc R U . . .
H18B H 0.445531 -0.121759 0.032196 0.067 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
C6 O2 H2 109.5 . . ?
C2 O1 H1 109.5 . . ?
O3 N3 O4 123.9(3) . . ?
O3 N3 C1 117.9(2) . . ?
O4 N3 C1 118.2(2) . . ?
C8 N2 C7 117.2(3) . . ?
C13 N1 C14 117.3(3) . . ?
O2 C6 C5 124.7(2) . . ?
O2 C6 C1 117.5(2) . . ?
C5 C6 C1 117.8(2) . . ?
C6 C1 C2 123.2(3) . . ?
C6 C1 N3 117.5(2) . . ?
C2 C1 N3 119.2(2) . . ?
O1 C2 C1 117.8(3) . . ?
O1 C2 C3 124.3(3) . . ?
C1 C2 C3 117.9(3) . . ?
C10 C11 C9 117.1(3) . . ?
C10 C11 C12 121.4(3) . . ?
C9 C11 C12 121.5(3) . . ?
N2 C7 C10 122.8(3) . . ?
N2 C7 H7 118.6 . . ?
C10 C7 H7 118.6 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C10 C11 120.0(3) . . ?
C7 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N1 C13 C15 123.3(3) . . ?
N1 C13 H13 118.3 . . ?
C15 C13 H13 118.3 . . ?
C8 C9 C11 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C11 C9 H9 120.3 . . ?
C11 C12 C12 111.6(3) . 3_777 ?
C11 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 3_777 . ?
C11 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 3_777 . ?
H12A C12 H12B 108.0 . . ?
N1 C14 C16 122.6(3) . . ?
N1 C14 H14 118.7 . . ?
C16 C14 H14 118.7 . . ?
C16 C17 C15 116.8(3) . . ?
C16 C17 C18 123.1(3) . . ?
C15 C17 C18 120.1(3) . . ?
N2 C8 C9 123.6(3) . . ?
N2 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C13 C15 C17 119.9(3) . . ?
C13 C15 H15 120.1 . . ?
C17 C15 H15 120.1 . . ?
C14 C16 C17 120.0(3) . . ?
C14 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C18 C17 112.9(4) 3_655 . ?
C18 C18 H18A 109.0 3_655 . ?
C17 C18 H18A 109.0 . . ?
C18 C18 H18B 109.0 3_655 . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
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 1.352(3) . ?
O2 H2 0.8200 . ?
O1 C2 1.350(4) . ?
O1 H1 0.8200 . ?
O4 N3 1.228(3) . ?
O3 N3 1.224(3) . ?
N3 C1 1.469(4) . ?
N2 C8 1.328(4) . ?
N2 C7 1.343(4) . ?
N1 C13 1.334(4) . ?
N1 C14 1.342(4) . ?
C6 C5 1.392(4) . ?
C6 C1 1.394(4) . ?
C1 C2 1.398(4) . ?
C2 C3 1.400(4) . ?
C11 C10 1.386(4) . ?
C11 C9 1.386(4) . ?
C11 C12 1.511(4) . ?
C7 C10 1.378(4) . ?
C7 H7 0.9300 . ?
C5 C4 1.386(4) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C13 C15 1.376(4) . ?
C13 H13 0.9300 . ?
C9 C8 1.382(5) . ?
C9 H9 0.9300 . ?
C12 C12 1.537(6) 3_777 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C16 1.382(5) . ?
C14 H14 0.9300 . ?
C17 C16 1.388(5) . ?
C17 C15 1.388(5) . ?
C17 C18 1.514(4) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C18 1.486(7) 3_655 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307086
