#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560045.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_1560045
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            'C19 H15 N3 O4'
_chemical_formula_weight         349.34
_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                105.585(7)
_cell_angle_beta                 102.978(7)
_cell_angle_gamma                95.062(7)
_cell_formula_units_Z            2
_cell_length_a                   7.7638(14)
_cell_length_b                   8.5897(15)
_cell_length_c                   12.723(2)
_cell_measurement_reflns_used    5658
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.4
_cell_volume                     786.4(2)
_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 0.988
_diffrn_measured_fraction_theta_max 0.982
_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  0.0391
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7168
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.392
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       Block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0530
_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)+(0.0982P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1769
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2234
_reflns_number_total             3538
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           5NRES-9AACR
_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        786.3(2)
_cod_database_code               1560045
_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   0.979
_shelx_estimated_absorpt_t_max   0.979
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
O1 O 0.5554(2) 0.10015(18) 0.27152(12) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.7822(2) -0.22913(19) -0.02638(13) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.872474 -0.160678 0.005270 0.049 Uiso 1 1 calc R U . . .
O3 O 0.9559(2) 0.0378(2) 0.10529(14) 0.0427(5) Uani 1 1 d . . . . .
N1 N 0.2317(2) 0.6350(2) 0.55075(14) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.236536 0.715373 0.609291 0.027 Uiso 1 1 calc R U . . .
N3 N 0.8378(2) 0.0623(2) 0.15944(15) 0.0265(4) Uani 1 1 d . . . . .
O4 O 0.8673(2) 0.1826(2) 0.24322(15) 0.0479(6) Uani 1 1 d . . . . .
N2 N 0.2836(2) 0.2822(2) 0.27473(14) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.334962 0.200456 0.284268 0.031 Uiso 1 1 calc R U . . .
H2B H 0.254118 0.295055 0.208644 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2875(3) 0.4950(2) 0.56593(17) 0.0209(5) Uani 1 1 d . . . . .
C19 C 0.2503(3) 0.3873(3) 0.36111(17) 0.0209(5) Uani 1 1 d . . . . .
C18 C 0.2996(3) 0.3662(2) 0.47215(17) 0.0198(5) Uani 1 1 d . . . . .
C12 C 0.1689(3) 0.6527(3) 0.44704(17) 0.0218(5) Uani 1 1 d . . . . .
C1 C 0.6759(3) -0.0486(2) 0.12276(16) 0.0208(5) Uani 1 1 d . . . . .
C7 C 0.1683(3) 0.5280(3) 0.34856(17) 0.0210(5) Uani 1 1 d . . . . .
C2 C 0.5357(3) -0.0162(2) 0.17994(17) 0.0215(5) Uani 1 1 d . . . . .
C6 C 0.6514(3) -0.1911(3) 0.02691(17) 0.0235(5) Uani 1 1 d . . . . .
C17 C 0.3608(3) 0.2233(3) 0.49234(18) 0.0247(5) Uani 1 1 d . . . . .
H17 H 0.369752 0.137689 0.431992 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0338(3) 0.6917(3) 0.2342(2) 0.0302(5) Uani 1 1 d . . . . .
H9 H -0.014418 0.704275 0.163654 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3363(3) 0.4786(3) 0.67554(18) 0.0255(5) Uani 1 1 d . . . . .
H14 H 0.328380 0.562768 0.737099 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3951(3) 0.3398(3) 0.69155(19) 0.0291(5) Uani 1 1 d . . . . .
H15 H 0.427984 0.330593 0.764300 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4916(3) -0.2950(3) -0.01254(18) 0.0317(6) Uani 1 1 d . . . . .
H5 H 0.476196 -0.389643 -0.072457 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3512(3) -0.2580(3) 0.03798(19) 0.0330(6) Uani 1 1 d . . . . .
H4 H 0.241568 -0.326953 0.008483 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1083(3) 0.7995(3) 0.43761(19) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.113244 0.883952 0.502319 0.034 Uiso 1 1 calc R U . . .
C8 C 0.0968(3) 0.5510(3) 0.24207(18) 0.0267(5) Uani 1 1 d . . . . .
H8 H 0.092856 0.468709 0.176472 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4067(3) 0.2101(3) 0.59960(19) 0.0275(5) Uani 1 1 d . . . . .
H16 H 0.445591 0.115463 0.611738 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3702(3) -0.1246(3) 0.12860(19) 0.0297(5) Uani 1 1 d . . . . .
H3 H 0.272379 -0.103574 0.157948 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0420(3) 0.8178(3) 0.3331(2) 0.0319(6) Uani 1 1 d . . . . .
H10 H 0.001879 0.914882 0.327386 0.038 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 . . ?
C12 N1 C13 122.56(17) . . ?
C12 N1 H1 118.7 . . ?
C13 N1 H1 118.7 . . ?
O4 N3 O3 118.99(18) . . ?
O4 N3 C1 121.52(18) . . ?
O3 N3 C1 119.48(17) . . ?
C19 N2 H2A 120.0 . . ?
C19 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C13 C14 119.86(18) . . ?
N1 C13 C18 120.37(19) . . ?
C14 C13 C18 119.8(2) . . ?
N2 C19 C18 120.2(2) . . ?
N2 C19 C7 121.42(19) . . ?
C18 C19 C7 118.35(18) . . ?
C13 C18 C17 118.3(2) . . ?
C13 C18 C19 118.46(19) . . ?
C17 C18 C19 123.19(19) . . ?
N1 C12 C7 120.83(19) . . ?
N1 C12 C11 119.48(18) . . ?
C7 C12 C11 119.7(2) . . ?
N3 C1 C6 119.22(18) . . ?
N3 C1 C2 119.85(17) . . ?
C6 C1 C2 120.92(18) . . ?
C12 C7 C8 118.5(2) . . ?
C12 C7 C19 118.39(19) . . ?
C8 C7 C19 122.96(19) . . ?
O1 C2 C3 120.8(2) . . ?
O1 C2 C1 123.67(19) . . ?
C3 C2 C1 115.49(19) . . ?
O2 C6 C5 117.70(19) . . ?
O2 C6 C1 122.68(19) . . ?
C5 C6 C1 119.6(2) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
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
O1 C2 1.283(2) . ?
O2 C6 1.359(3) . ?
O2 H2 0.8200 . ?
O3 N3 1.264(2) . ?
N1 C12 1.354(3) . ?
N1 C13 1.360(3) . ?
N1 H1 0.8600 . ?
N3 O4 1.230(2) . ?
N3 C1 1.411(3) . ?
N2 C19 1.314(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C13 C14 1.409(3) . ?
C13 C18 1.420(3) . ?
C19 C18 1.443(3) . ?
C19 C7 1.444(3) . ?
C18 C17 1.420(3) . ?
C12 C7 1.411(3) . ?
C12 C11 1.410(3) . ?
C1 C6 1.440(3) . ?
C1 C2 1.446(3) . ?
C7 C8 1.417(3) . ?
C2 C3 1.425(3) . ?
C6 C5 1.368(3) . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C9 C8 1.363(3) . ?
C9 C10 1.408(3) . ?
C9 H9 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.403(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.359(3) . ?
C4 H4 0.9300 . ?
C11 C10 1.370(3) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
