#------------------------------------------------------------------------------
#$Date: 2021-03-05 19:43:22 +0100 (vie 05 de mar de 2021) $
#$Revision: 262771 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/00/1560047.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_1560047
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            'C42 H34 N8 O8'
_chemical_formula_weight         778.77
_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                106.397(7)
_cell_angle_beta                 103.133(7)
_cell_angle_gamma                90.486(6)
_cell_formula_units_Z            1
_cell_length_a                   7.4323(10)
_cell_length_b                   9.1138(12)
_cell_length_c                   14.562(2)
_cell_measurement_reflns_used    8552
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     918.7(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0236
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9526
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         3.004
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.408
_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         0.332
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4200
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0453
_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)+(0.0807P)²+0.2379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3376
_reflns_number_total             4200
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           7NRES-44BP
_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               1560047
_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   0.980
_shelx_estimated_absorpt_t_max   0.980
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 0.21704(15) 0.14715(12) 0.88284(9) 0.0252(3) Uani 1 1 d . . . . .
H1 H 0.319935 0.192423 0.897080 0.038 Uiso 1 1 calc R U . . .
O2 O -0.10204(15) -0.34219(11) 0.74466(8) 0.0248(3) Uani 1 1 d . . . . .
H2 H -0.096850 -0.427216 0.707049 0.037 Uiso 1 1 calc R U . . .
O3 O -0.15821(16) -0.08161(13) 0.90132(9) 0.0295(3) Uani 1 1 d . . . . .
N4 N -0.10142(16) -0.03893(13) 0.83987(9) 0.0186(3) Uani 1 1 d . . . . .
O4 O -0.17775(15) 0.05119(13) 0.79823(9) 0.0284(3) Uani 1 1 d . . . . .
C20 C 0.0598(2) -0.25839(16) 0.76464(11) 0.0194(3) Uani 1 1 d . . . . .
C24 C 0.2264(2) -0.00238(16) 0.83693(11) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.2204(2) -0.31727(17) 0.73899(12) 0.0246(3) Uani 1 1 d . . . . .
H21 H 0.220309 -0.420693 0.705750 0.029 Uiso 1 1 calc R U . . .
N1 N 0.54938(18) 0.30714(15) 0.93048(10) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.9057(2) 0.45992(16) 0.98543(10) 0.0199(3) Uani 1 1 d . . . . .
C19 C 0.06763(19) -0.10135(16) 0.81344(11) 0.0180(3) Uani 1 1 d . . . . .
C23 C 0.3858(2) -0.06496(18) 0.81172(12) 0.0249(3) Uani 1 1 d . . . . .
H23 H 0.494929 -0.002944 0.827173 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3799(2) -0.22061(19) 0.76339(13) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.486486 -0.261309 0.746840 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5828(2) 0.43088(19) 0.90304(12) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.484398 0.465825 0.864840 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8703(2) 0.33113(18) 1.01360(12) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.965929 0.292811 1.051418 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7546(2) 0.50992(19) 0.92796(13) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.769851 0.595460 0.906852 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6935(2) 0.25988(18) 0.98557(13) 0.0282(4) Uani 1 1 d . . . . .
H18 H 0.673564 0.174568 1.006083 0.034 Uiso 1 1 calc R U . . .
N3 N 0.0849(2) 0.62517(14) 0.36843(11) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.0862(2) 0.81472(17) 0.52020(12) 0.0256(3) Uani 1 1 d . . . . .
H1A H 0.111178 0.840348 0.588598 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0181(2) 0.92136(15) 0.47266(11) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.4756(2) 1.08148(17) 0.51344(12) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.3854(2) 1.38947(17) 0.56473(12) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.4143(3) 1.15596(19) 0.44372(13) 0.0343(4) Uani 1 1 d . . . . .
H12 H 0.401119 1.104982 0.377235 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1174(2) 0.66986(17) 0.46629(13) 0.0277(4) Uani 1 1 d . . . . .
H2A H 0.163354 0.600342 0.500164 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3720(3) 1.3080(2) 0.47285(15) 0.0383(4) Uani 1 1 d . . . . .
H11 H 0.331262 1.355318 0.423856 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0213(4) 0.7274(2) 0.32252(15) 0.0535(6) Uani 1 1 d . . . . .
H4 H -0.001496 0.698725 0.254109 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4930(4) 1.1663(3) 0.61003(15) 0.0623(8) Uani 1 1 d . . . . .
H8 H 0.535663 1.122823 0.660800 0.075 Uiso 1 1 calc R U . . .
C5 C -0.0132(4) 0.8747(2) 0.37083(14) 0.0517(6) Uani 1 1 d . . . . .
H5 H -0.057295 0.942143 0.334993 0.062 Uiso 1 1 calc R U . . .
C9 C 0.4463(4) 1.3175(3) 0.63100(16) 0.0680(8) Uani 1 1 d . . . . .
H9 H 0.459066 1.371918 0.696893 0.082 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
O3 N4 O4 124.08(12) . . ?
O3 N4 C19 117.95(12) . . ?
O4 N4 C19 117.96(12) . . ?
O2 C20 C21 124.38(13) . . ?
O2 C20 C19 117.99(12) . . ?
C21 C20 C19 117.63(13) . . ?
O1 C24 C19 118.12(12) . . ?
O1 C24 C23 124.08(14) . . ?
C19 C24 C23 117.80(13) . . ?
C22 C21 C20 119.59(14) . . ?
C14 N1 C18 116.63(14) . . ?
C17 C16 C15 116.45(14) . . ?
C17 C16 C16 121.67(17) . 2_767 ?
C15 C16 C16 121.88(17) . 2_767 ?
C24 C19 C20 123.30(13) . . ?
C24 C19 N4 118.95(12) . . ?
C20 C19 N4 117.74(12) . . ?
C22 C23 C24 119.42(14) . . ?
C21 C22 C23 122.24(14) . . ?
N1 C14 C15 123.98(16) . . ?
C18 C17 C16 120.15(15) . . ?
C14 C15 C16 119.34(15) . . ?
N1 C18 C17 123.44(15) . . ?
C4 N3 C2 116.85(14) . . ?
C6 C1 C2 120.17(15) . . ?
C1 C6 C5 116.28(14) . . ?
C1 C6 C6 122.20(17) . 2_576 ?
C5 C6 C6 121.52(17) . 2_576 ?
C12 C7 C8 116.15(15) . . ?
C12 C7 C7 122.13(18) . 2_676 ?
C8 C7 C7 121.71(19) . 2_676 ?
C11 N2 C9 115.06(15) . . ?
C7 C12 C11 119.76(16) . . ?
N3 C2 C1 123.24(15) . . ?
N2 C11 C12 124.66(17) . . ?
N3 C4 C5 123.56(17) . . ?
C7 C8 C9 119.39(19) . . ?
C4 C5 C6 119.90(17) . . ?
N2 C9 C8 124.97(19) . . ?
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 C24 1.3482(17) . ?
O2 C20 1.3473(18) . ?
O3 N4 1.2229(17) . ?
N4 O4 1.2234(16) . ?
N4 C19 1.4692(17) . ?
C20 C21 1.397(2) . ?
C20 C19 1.4009(19) . ?
C24 C19 1.396(2) . ?
C24 C23 1.398(2) . ?
C21 C22 1.386(2) . ?
N1 C14 1.337(2) . ?
N1 C18 1.337(2) . ?
C16 C17 1.390(2) . ?
C16 C15 1.403(2) . ?
C16 C16 1.488(3) 2_767 ?
C23 C22 1.390(2) . ?
C14 C15 1.381(2) . ?
C17 C18 1.381(2) . ?
N3 C4 1.325(2) . ?
N3 C2 1.330(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.384(2) . ?
C6 C5 1.385(2) . ?
C6 C6 1.490(3) 2_576 ?
C7 C12 1.372(2) . ?
C7 C8 1.376(2) . ?
C7 C7 1.495(3) 2_676 ?
N2 C11 1.315(2) . ?
N2 C9 1.315(3) . ?
C12 C11 1.391(2) . ?
C4 C5 1.384(2) . ?
C8 C9 1.390(3) . ?
