#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560056.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_1560056
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            'C38 H42 N8 O8'
_chemical_formula_weight         738.79
_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                95.531(7)
_cell_angle_beta                 101.446(7)
_cell_angle_gamma                111.676(8)
_cell_formula_units_Z            1
_cell_length_a                   7.4104(7)
_cell_length_b                   8.8964(9)
_cell_length_c                   15.7722(15)
_cell_measurement_reflns_used    8594
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     930.47(17)
_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 0.997
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       Block
_exptl_crystal_F_000             390
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0517
_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)+(0.0713P)²+0.4390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3261
_reflns_number_total             4270
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           16NRES-TMP-22BP
_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               1560056
_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
O1 O 0.6072(2) 0.54850(19) 0.39526(11) 0.0435(4) Uani 1 1 d . . . . .
O2 O 0.6668(2) 0.75298(18) 0.32810(11) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.33133(19) 0.37213(15) 0.21274(9) 0.0304(3) Uani 1 1 d . . . . .
H3 H 0.254544 0.297527 0.171892 0.046 Uiso 1 1 calc R U . . .
O4 O 0.36697(18) 0.80485(15) 0.41924(8) 0.0280(3) Uani 1 1 d . . . . .
H4 H 0.300636 0.852008 0.436226 0.042 Uiso 1 1 calc R U . . .
N4 N 0.5521(2) 0.63146(17) 0.34811(9) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.3358(2) 0.5858(2) 0.31408(11) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.2297(3) 0.4542(2) 0.24416(11) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.2482(2) 0.6802(2) 0.35159(11) 0.0214(4) Uani 1 1 d . . . . .
C18 C 0.0265(3) 0.4174(2) 0.20989(12) 0.0261(4) Uani 1 1 d . . . . .
H18 H -0.048787 0.330866 0.162732 0.031 Uiso 1 1 calc R U . . .
C19 C -0.0623(3) 0.5108(2) 0.24662(12) 0.0260(4) Uani 1 1 d . . . . .
H19 H -0.197832 0.485379 0.223393 0.031 Uiso 1 1 calc R U . . .
C20 C 0.0443(3) 0.6404(2) 0.31671(12) 0.0252(4) Uani 1 1 d . . . . .
H20 H -0.019211 0.700573 0.340390 0.030 Uiso 1 1 calc R U . . .
N1 N 0.0879(2) 0.12529(19) 0.07224(10) 0.0289(4) Uani 1 1 d . . . . .
C7 C 0.2525(3) 0.3251(2) -0.01269(15) 0.0401(5) Uani 1 1 d . . . . .
H7A H 0.266513 0.401110 0.038138 0.060 Uiso 1 1 calc R U . . .
H7B H 0.193097 0.354556 -0.064817 0.060 Uiso 1 1 calc R U . . .
H7C H 0.382217 0.328867 -0.015618 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1197(3) 0.1531(2) -0.00606(13) 0.0294(4) Uani 1 1 d . . . . .
C9 C -0.0316(3) -0.0262(2) 0.08106(13) 0.0271(4) Uani 1 1 d . . . . .
C10 C -0.0658(3) -0.0514(3) 0.16873(13) 0.0362(5) Uani 1 1 d . . . . .
H10A H -0.004228 0.052402 0.208802 0.054 Uiso 1 1 calc R U . . .
H10B H -0.007992 -0.125167 0.190118 0.054 Uiso 1 1 calc R U . . .
H10C H -0.207422 -0.097657 0.164242 0.054 Uiso 1 1 calc R U . . .
N2 N 0.5635(2) 1.1208(2) 0.10899(11) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.4262(3) 0.9491(3) 0.20808(13) 0.0331(4) Uani 1 1 d . . . . .
H1 H 0.413547 0.938380 0.264924 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3378(3) 0.8147(3) 0.14009(14) 0.0377(5) Uani 1 1 d . . . . .
H2 H 0.260065 0.712103 0.150072 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3657(3) 0.8337(2) 0.05689(13) 0.0315(4) Uani 1 1 d . . . . .
H3A H 0.307894 0.744201 0.010436 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4808(2) 0.9877(2) 0.04417(11) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.5335(3) 1.0991(2) 0.18930(13) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.588433 1.190728 0.234447 0.038 Uiso 1 1 calc R U . . .
N3 N 0.1436(2) 0.94649(17) 0.48337(9) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.0386(3) 0.7194(2) 0.56171(14) 0.0334(4) Uani 1 1 d . . . . .
H11A H 0.154265 0.708107 0.548174 0.050 Uiso 1 1 calc R U . . .
H11B H -0.079137 0.622377 0.533187 0.050 Uiso 1 1 calc R U . . .
H11C H 0.054573 0.733242 0.624250 0.050 Uiso 1 1 calc R U . . .
C12 C 0.0171(3) 0.8669(2) 0.52969(11) 0.0223(4) Uani 1 1 d . . . . .
C13 C 0.1294(3) 1.0790(2) 0.45359(11) 0.0221(4) Uani 1 1 d . . . . .
C14 C 0.2786(3) 1.1669(2) 0.40453(13) 0.0307(4) Uani 1 1 d . . . . .
H14A H 0.358103 1.277334 0.436110 0.046 Uiso 1 1 calc R U . . .
H14B H 0.208699 1.169920 0.346960 0.046 Uiso 1 1 calc R U . . .
H14C H 0.364376 1.109819 0.399134 0.046 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
O1 N4 O2 123.57(15) . . ?
O1 N4 C15 118.77(15) . . ?
O2 N4 C15 117.65(14) . . ?
C16 C15 C17 123.10(15) . . ?
C16 C15 N4 118.63(14) . . ?
C17 C15 N4 118.23(14) . . ?
O3 C16 C15 117.79(15) . . ?
O3 C16 C18 124.29(15) . . ?
C15 C16 C18 117.91(15) . . ?
O4 C17 C15 117.56(14) . . ?
O4 C17 C20 124.41(15) . . ?
C15 C17 C20 118.03(15) . . ?
C19 C18 C16 119.51(16) . . ?
C20 C19 C18 122.07(16) . . ?
C19 C20 C17 119.37(16) . . ?
C8 N1 C9 120.16(16) . . ?
N1 C8 C9 121.21(18) . 2 ?
N1 C8 C7 118.12(17) . . ?
C9 C8 C7 120.67(18) 2 . ?
N1 C9 C8 118.63(17) . 2 ?
N1 C9 C10 118.49(17) . . ?
C8 C9 C10 122.88(18) 2 . ?
C4 N2 C5 117.49(16) . . ?
C5 C1 C2 118.02(18) . . ?
C1 C2 C3 119.53(19) . . ?
C4 C3 C2 118.79(18) . . ?
N2 C4 C3 122.52(17) . . ?
N2 C4 C4 117.07(19) . 2_675 ?
C3 C4 C4 120.4(2) . 2_675 ?
N2 C5 C1 123.59(18) . . ?
C12 N3 C13 119.53(15) . . ?
N3 C12 C13 120.24(15) . 2_576 ?
N3 C12 C11 117.65(15) . . ?
C13 C12 C11 122.11(16) 2_576 . ?
N3 C13 C12 120.23(16) . 2_576 ?
N3 C13 C14 117.49(15) . . ?
C12 C13 C14 122.27(16) 2_576 . ?
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 N4 1.213(2) . ?
O2 N4 1.218(2) . ?
O3 C16 1.353(2) . ?
O4 C17 1.349(2) . ?
N4 C15 1.469(2) . ?
C15 C16 1.390(2) . ?
C15 C17 1.392(2) . ?
C16 C18 1.394(2) . ?
C17 C20 1.396(2) . ?
C18 C19 1.386(3) . ?
C19 C20 1.382(3) . ?
N1 C8 1.332(2) . ?
N1 C9 1.350(2) . ?
C7 C8 1.509(3) . ?
C8 C9 1.412(3) 2 ?
C9 C10 1.478(3) . ?
N2 C4 1.344(2) . ?
N2 C5 1.348(2) . ?
C1 C5 1.374(3) . ?
C1 C2 1.380(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.379(3) . ?
C4 C4 1.497(3) 2_675 ?
N3 C12 1.340(2) . ?
N3 C13 1.342(2) . ?
C11 C12 1.502(2) . ?
C12 C13 1.398(2) 2_576 ?
C13 C14 1.500(2) . ?
