#------------------------------------------------------------------------------
#$Date: 2021-03-05 19:43:22 +0100 (vie 05 de mar de 2021) $
#$Revision: 262771 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/00/1560059.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_1560059
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            'C50 H52 N8 O8'
_chemical_formula_weight         892.99
_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                83.021(6)
_cell_angle_beta                 82.842(6)
_cell_angle_gamma                88.111(6)
_cell_formula_units_Z            1
_cell_length_a                   7.7634(12)
_cell_length_b                   8.9486(14)
_cell_length_c                   16.368(3)
_cell_measurement_reflns_used    9566
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.1
_cell_volume                     1119.7(3)
_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 0.997
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11576
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         3.067
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       Block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5114
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0630
_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)+(0.0718P)²+1.6202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1944
_refine_ls_wR_factor_ref         0.2061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3585
_reflns_number_total             5114
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           19NTES-TMP-PYR-4DMAP
_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               1560059
_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   0.982
_shelx_estimated_absorpt_t_max   0.982
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
O4 O 0.9664(3) 0.6218(2) 0.35641(14) 0.0311(5) Uani 1 1 d . . . . .
H4 H 1.040209 0.668948 0.373751 0.047 Uiso 1 1 calc R U . . .
N1 N 0.7532(3) 0.4694(3) 0.27859(14) 0.0226(5) Uani 1 1 d . . . . .
O3 O 0.8895(3) 0.2465(2) 0.18933(14) 0.0322(5) Uani 1 1 d . . . . .
H3 H 0.941730 0.197163 0.154721 0.048 Uiso 1 1 calc R U . . .
C14 C 1.4707(3) 0.9246(3) 0.00892(17) 0.0227(6) Uani 1 1 d . . . . .
C5 C 1.2219(4) 0.4850(3) 0.30280(18) 0.0252(6) Uani 1 1 d . . . . .
H5 H 1.296170 0.537553 0.328934 0.030 Uiso 1 1 calc R U . . .
C1 C 0.9398(3) 0.4334(3) 0.27193(16) 0.0212(5) Uani 1 1 d . . . . .
O1 O 0.6651(3) 0.4366(3) 0.34456(14) 0.0428(6) Uani 1 1 d . . . . .
O2 O 0.6945(3) 0.5323(3) 0.21745(16) 0.0487(7) Uani 1 1 d . . . . .
C3 C 1.1821(4) 0.2929(3) 0.21445(18) 0.0276(6) Uani 1 1 d . . . . .
H3A H 1.229767 0.219142 0.182549 0.033 Uiso 1 1 calc R U . . .
C8 C 1.4317(4) 0.8451(3) -0.05669(19) 0.0282(6) Uani 1 1 d . . . . .
C2 C 1.0039(4) 0.3222(3) 0.22311(17) 0.0236(6) Uani 1 1 d . . . . .
C12 C 1.4501(4) 0.8543(3) 0.09164(18) 0.0272(6) Uani 1 1 d . . . . .
C6 C 1.0438(4) 0.5165(3) 0.31258(16) 0.0226(6) Uani 1 1 d . . . . .
C4 C 1.2877(4) 0.3754(3) 0.25409(18) 0.0276(6) Uani 1 1 d . . . . .
H4A H 1.406764 0.356307 0.247698 0.033 Uiso 1 1 calc R U . . .
C7 C 1.4527(4) 0.9207(4) -0.13959(19) 0.0331(7) Uani 1 1 d . . . . .
H7 H 1.426328 0.870442 -0.182823 0.040 Uiso 1 1 calc R U . . .
C13 C 1.4904(4) 0.9375(4) 0.15622(19) 0.0333(7) Uani 1 1 d . . . . .
H13 H 1.476793 0.892173 0.210804 0.040 Uiso 1 1 calc R U . . .
C11 C 1.3931(4) 0.7051(4) 0.1068(2) 0.0353(7) Uani 1 1 d . . . . .
H11 H 1.379326 0.657217 0.160878 0.042 Uiso 1 1 calc R U . . .
C9 C 1.3749(4) 0.6968(4) -0.0375(2) 0.0373(8) Uani 1 1 d . . . . .
H9 H 1.348593 0.643525 -0.079647 0.045 Uiso 1 1 calc R U . . .
C10 C 1.3574(4) 0.6287(4) 0.0434(2) 0.0409(8) Uani 1 1 d . . . . .
H10 H 1.320935 0.529597 0.054945 0.049 Uiso 1 1 calc R U . . .
N2 N 0.0153(3) 0.0765(3) 0.06661(14) 0.0235(5) Uani 1 1 d . . . . .
C17 C -0.0266(3) -0.0691(3) 0.07848(17) 0.0224(6) Uani 1 1 d . . . . .
C16 C 0.0430(3) 0.1466(3) -0.01085(17) 0.0228(6) Uani 1 1 d . . . . .
C18 C -0.0504(4) -0.1448(3) 0.16599(18) 0.0324(7) Uani 1 1 d . . . . .
H18A H 0.039526 -0.219640 0.173301 0.049 Uiso 1 1 calc R U . . .
H18B H -0.161592 -0.191865 0.177063 0.049 Uiso 1 1 calc R U . . .
H18C H -0.044489 -0.071213 0.203585 0.049 Uiso 1 1 calc R U . . .
C15 C 0.0957(4) 0.3082(3) -0.0211(2) 0.0319(7) Uani 1 1 d . . . . .
H15A H 0.067804 0.348953 0.030636 0.048 Uiso 1 1 calc R U . . .
H15B H 0.034574 0.364627 -0.062572 0.048 Uiso 1 1 calc R U . . .
H15C H 0.218437 0.314497 -0.037994 0.048 Uiso 1 1 calc R U . . .
N3 N 0.1487(3) 0.8039(3) 0.41817(17) 0.0341(6) Uani 1 1 d . . . . .
N4 N 0.3087(3) 1.1481(3) 0.54141(15) 0.0284(5) Uani 1 1 d . . . . .
C23 C 0.2588(3) 1.0356(3) 0.50138(17) 0.0243(6) Uani 1 1 d . . . . .
C22 C 0.2488(4) 0.8856(3) 0.53792(19) 0.0299(6) Uani 1 1 d . . . . .
H22 H 0.279286 0.859630 0.591049 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3480(4) 1.1189(4) 0.62660(19) 0.0344(7) Uani 1 1 d . . . . .
H25A H 0.251559 1.070105 0.660726 0.052 Uiso 1 1 calc R U . . .
H25B H 0.368849 1.212455 0.646552 0.052 Uiso 1 1 calc R U . . .
H25C H 0.449529 1.055056 0.628717 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2136(4) 1.0639(3) 0.42001(18) 0.0295(6) Uani 1 1 d . . . . .
H21 H 0.220125 1.160708 0.391909 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1939(4) 0.7771(3) 0.4950(2) 0.0321(7) Uani 1 1 d . . . . .
H20 H 0.187586 0.678755 0.521010 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3248(4) 1.3006(3) 0.4999(2) 0.0339(7) Uani 1 1 d . . . . .
H24A H 0.403275 1.300921 0.449724 0.051 Uiso 1 1 calc R U . . .
H24B H 0.368797 1.363717 0.535728 0.051 Uiso 1 1 calc R U . . .
H24C H 0.212958 1.338187 0.486920 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1598(4) 0.9472(4) 0.38265(19) 0.0327(7) Uani 1 1 d . . . . .
H19 H 0.129024 0.968814 0.329300 0.039 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 N1 O2 123.1(2) . . ?
O1 N1 C1 118.7(2) . . ?
O2 N1 C1 118.1(2) . . ?
C12 C14 C14 120.0(3) . 2_875 ?
C12 C14 C8 120.2(3) . . ?
C14 C14 C8 119.8(3) 2_875 . ?
C4 C5 C6 119.8(3) . . ?
C2 C1 C6 123.7(2) . . ?
C2 C1 N1 118.3(2) . . ?
C6 C1 N1 117.9(2) . . ?
C4 C3 C2 119.1(3) . . ?
C9 C8 C14 118.7(3) . . ?
C9 C8 C7 122.8(3) . . ?
C14 C8 C7 118.5(3) . . ?
O3 C2 C1 118.0(2) . . ?
O3 C2 C3 124.0(2) . . ?
C1 C2 C3 117.9(3) . . ?
C11 C12 C14 118.4(3) . . ?
C11 C12 C13 122.8(3) . . ?
C14 C12 C13 118.8(3) . . ?
O4 C6 C1 117.8(2) . . ?
O4 C6 C5 125.1(2) . . ?
C1 C6 C5 117.2(2) . . ?
C5 C4 C3 122.3(3) . . ?
C13 C7 C8 121.5(3) 2_875 . ?
C7 C13 C12 121.4(3) 2_875 . ?
C10 C11 C12 121.1(3) . . ?
C10 C9 C8 120.6(3) . . ?
C11 C10 C9 121.0(3) . . ?
C17 N2 C16 119.3(2) . . ?
N2 C17 C16 120.3(2) . 2 ?
N2 C17 C18 117.6(2) . . ?
C16 C17 C18 122.1(3) 2 . ?
N2 C16 C17 120.4(2) . 2 ?
N2 C16 C15 117.3(2) . . ?
C17 C16 C15 122.3(3) 2 . ?
C20 N3 C19 116.2(3) . . ?
C23 N4 C24 120.6(2) . . ?
C23 N4 C25 121.0(3) . . ?
C24 N4 C25 118.4(2) . . ?
N4 C23 C22 122.4(3) . . ?
N4 C23 C21 121.4(3) . . ?
C22 C23 C21 116.1(3) . . ?
C20 C22 C23 119.8(3) . . ?
C19 C21 C23 119.4(3) . . ?
N3 C20 C22 124.2(3) . . ?
N3 C19 C21 124.2(3) . . ?
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
O4 C6 1.336(3) . ?
N1 O1 1.213(3) . ?
N1 O2 1.219(3) . ?
N1 C1 1.467(3) . ?
O3 C2 1.344(3) . ?
C14 C12 1.414(4) . ?
C14 C14 1.423(5) 2_875 ?
C14 C8 1.426(4) . ?
C5 C4 1.383(4) . ?
C5 C6 1.395(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.393(4) . ?
C3 C4 1.388(4) . ?
C3 C2 1.393(4) . ?
C8 C9 1.399(4) . ?
C8 C7 1.433(4) . ?
C12 C11 1.404(4) . ?
C12 C13 1.434(4) . ?
C7 C13 1.342(5) 2_875 ?
C11 C10 1.371(5) . ?
C9 C10 1.381(5) . ?
N2 C17 1.338(4) . ?
N2 C16 1.340(4) . ?
C17 C16 1.396(4) 2 ?
C17 C18 1.500(4) . ?
C16 C15 1.500(4) . ?
N3 C20 1.340(4) . ?
N3 C19 1.343(4) . ?
N4 C23 1.357(4) . ?
N4 C24 1.451(4) . ?
N4 C25 1.455(4) . ?
C23 C22 1.402(4) . ?
C23 C21 1.411(4) . ?
C22 C20 1.372(4) . ?
C21 C19 1.374(4) . ?
