#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560067.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_1560067
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            'C72 H48 Cl4 N10 O4'
_chemical_formula_weight         1259.00
_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                108.220(8)
_cell_angle_beta                 104.061(7)
_cell_angle_gamma                101.072(7)
_cell_formula_units_Z            1
_cell_length_a                   10.807(5)
_cell_length_b                   12.145(5)
_cell_length_c                   12.466(6)
_cell_measurement_reflns_used    7173
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.7
_cell_measurement_theta_min      3.0
_cell_volume                     1442.4(11)
_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 0.975
_diffrn_measured_fraction_theta_max 0.959
_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  0.1036
_diffrn_reflns_av_unetI/netI     0.1296
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11846
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.041
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       Prism
_exptl_crystal_F_000             650
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.683
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1675
_refine_ls_R_factor_gt           0.0880
_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)+(0.1435P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2076
_refine_ls_wR_factor_ref         0.2692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3189
_reflns_number_total             6333
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           27CRES-PHE
_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        1442.3(11)
_cod_database_code               1560067
_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   0.948
_shelx_estimated_absorpt_t_max   0.948
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
Cl01 Cl 0.20780(12) -0.03104(11) 0.94958(10) 0.0367(3) Uani 1 1 d . . . . .
Cl02 Cl 0.00215(12) 0.34369(11) 1.08446(10) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.0875(3) 0.4082(3) 0.9012(3) 0.0371(8) Uani 1 1 d . . . . .
H2 H 0.117313 0.425655 0.852210 0.056 Uiso 1 1 calc R U . . .
O1 O 0.2811(3) 0.0814(3) 0.7878(3) 0.0391(8) Uani 1 1 d . . . . .
H1 H 0.299973 0.115369 0.743980 0.059 Uiso 1 1 calc R U . . .
N3 N 0.3382(4) 0.2067(3) 0.6457(3) 0.0288(9) Uani 1 1 d . . . . .
N5 N 0.5352(4) 0.0651(3) 0.4295(3) 0.0310(9) Uani 1 1 d . . . . .
N1 N 0.1729(4) 0.4791(4) 0.7303(3) 0.0300(9) Uani 1 1 d . . . . .
N2 N 0.2504(4) 0.5775(4) 0.5690(3) 0.0330(9) Uani 1 1 d . . . . .
N4 N 0.4017(4) 0.3300(3) 0.4977(3) 0.0300(9) Uani 1 1 d . . . . .
C4 C 0.1097(4) 0.1615(4) 1.0051(4) 0.0303(11) Uani 1 1 d . . . . .
H4 H 0.084480 0.133461 1.060279 0.036 Uiso 1 1 calc R U . . .
C19 C 0.4272(4) 0.3175(4) 0.6922(4) 0.0282(10) Uani 1 1 d . . . . .
C7 C 0.2672(4) 0.5875(4) 0.7696(4) 0.0312(11) Uani 1 1 d . . . . .
C12 C 0.3050(5) 0.6374(4) 0.6882(4) 0.0313(11) Uani 1 1 d . . . . .
C2 C 0.1178(4) 0.3093(4) 0.9115(4) 0.0303(11) Uani 1 1 d . . . . .
C6 C 0.2161(4) 0.1434(4) 0.8543(4) 0.0297(10) Uani 1 1 d . . . . .
C34 C 0.4449(4) -0.0462(4) 0.3798(4) 0.0292(10) Uani 1 1 d . . . . .
C20 C 0.4888(4) 0.3741(4) 0.8178(4) 0.0317(11) Uani 1 1 d . . . . .
H20 H 0.470152 0.334021 0.867157 0.038 Uiso 1 1 calc R U . . .
C1 C 0.1854(4) 0.2451(4) 0.8423(4) 0.0311(11) Uani 1 1 d . . . . .
H1A H 0.210240 0.272338 0.786499 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3126(4) 0.2196(4) 0.4517(4) 0.0282(10) Uani 1 1 d . . . . .
C14 C 0.0946(5) 0.4038(4) 0.4042(4) 0.0342(11) Uani 1 1 d . . . . .
H14 H 0.120403 0.434296 0.350740 0.041 Uiso 1 1 calc R U . . .
C33 C 0.5917(4) 0.1117(4) 0.5500(4) 0.0296(10) Uani 1 1 d . . . . .
C8 C 0.3297(5) 0.6544(4) 0.8945(4) 0.0324(11) Uani 1 1 d . . . . .
H8 H 0.306812 0.623307 0.948666 0.039 Uiso 1 1 calc R U . . .
C26 C 0.2500(5) 0.1620(5) 0.3257(4) 0.0359(12) Uani 1 1 d . . . . .
H26 H 0.272573 0.200565 0.276355 0.043 Uiso 1 1 calc R U . . .
C30 C 0.2769(4) 0.1556(4) 0.5252(4) 0.0292(10) Uani 1 1 d . . . . .
C24 C 0.4575(4) 0.3795(4) 0.6171(4) 0.0302(11) Uani 1 1 d . . . . .
C13 C 0.1572(4) 0.4705(4) 0.5298(4) 0.0301(10) Uani 1 1 d . . . . .
C18 C 0.1174(5) 0.4202(4) 0.6115(4) 0.0306(11) Uani 1 1 d . . . . .
C23 C 0.5509(5) 0.4977(4) 0.6709(4) 0.0353(11) Uani 1 1 d . . . . .
H23 H 0.572889 0.538429 0.623049 0.042 Uiso 1 1 calc R U . . .
C35 C 0.3822(5) -0.0987(5) 0.2544(4) 0.0370(12) Uani 1 1 d . . . . .
H35 H 0.405556 -0.057980 0.206992 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0160(5) 0.3086(4) 0.5634(4) 0.0364(12) Uani 1 1 d . . . . .
H17 H -0.011629 0.275591 0.614594 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1758(4) 0.1003(4) 0.9364(4) 0.0301(10) Uani 1 1 d . . . . .
C3 C 0.0803(4) 0.2642(4) 0.9932(4) 0.0324(11) Uani 1 1 d . . . . .
C21 C 0.5762(5) 0.4884(4) 0.8658(4) 0.0341(11) Uani 1 1 d . . . . .
H21 H 0.615744 0.525923 0.948190 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0014(5) 0.2971(5) 0.3621(4) 0.0378(12) Uani 1 1 d . . . . .
H15 H -0.041243 0.254795 0.280259 0.045 Uiso 1 1 calc R U . . .
C32 C 0.6871(5) 0.2280(4) 0.6063(4) 0.0373(12) Uani 1 1 d . . . . .
H32 H 0.708354 0.272438 0.561282 0.045 Uiso 1 1 calc R U . . .
C29 C 0.1795(5) 0.0418(4) 0.4721(4) 0.0363(11) Uani 1 1 d . . . . .
H29 H 0.154675 0.001357 0.519275 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0416(5) 0.2491(5) 0.4437(4) 0.0379(12) Uani 1 1 d . . . . .
H16 H -0.108372 0.175962 0.414034 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4023(5) 0.7524(5) 0.7348(4) 0.0364(12) Uani 1 1 d . . . . .
H11 H 0.427097 0.786074 0.682931 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4230(5) 0.7641(5) 0.9349(4) 0.0376(12) Uani 1 1 d . . . . .
H9 H 0.463336 0.806896 1.016689 0.045 Uiso 1 1 calc R U . . .
C31 C 0.7475(5) 0.2740(5) 0.7278(5) 0.0409(13) Uani 1 1 d . . . . .
H31 H 0.812263 0.348808 0.764881 0.049 Uiso 1 1 calc R U . . .
C36 C 0.2879(5) -0.2086(5) 0.2030(4) 0.0403(13) Uani 1 1 d . . . . .
H36 H 0.246091 -0.241166 0.120751 0.048 Uiso 1 1 calc R U . . .
C28 C 0.1223(5) -0.0080(5) 0.3520(5) 0.0412(13) Uani 1 1 d . . . . .
H28 H 0.058149 -0.083133 0.317398 0.049 Uiso 1 1 calc R U . . .
C22 C 0.6079(5) 0.5512(5) 0.7918(4) 0.0422(13) Uani 1 1 d . . . . .
H22 H 0.667480 0.628715 0.826263 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4593(5) 0.8135(5) 0.8551(4) 0.0403(12) Uani 1 1 d . . . . .
H10 H 0.522861 0.888551 0.884694 0.048 Uiso 1 1 calc R U . . .
C27 C 0.1577(5) 0.0514(5) 0.2766(4) 0.0425(13) Uani 1 1 d . . . . .
H27 H 0.117608 0.014534 0.194237 0.051 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'
Cl Cl 0.1484 0.1585 '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
C2 O2 H2 109.5 . . ?
C6 O1 H1 109.5 . . ?
C19 N3 C30 118.2(4) . . ?
C34 N5 C33 117.0(4) . . ?
C18 N1 C7 116.9(4) . . ?
C13 N2 C12 117.3(4) . . ?
C24 N4 C25 116.6(4) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N3 C19 C20 119.1(4) . . ?
N3 C19 C24 121.0(4) . . ?
C20 C19 C24 119.9(4) . . ?
N1 C7 C8 119.7(4) . . ?
N1 C7 C12 121.6(4) . . ?
C8 C7 C12 118.7(4) . . ?
N2 C12 C11 119.7(4) . . ?
N2 C12 C7 121.3(4) . . ?
C11 C12 C7 119.0(4) . . ?
O2 C2 C3 119.8(4) . . ?
O2 C2 C1 123.3(4) . . ?
C3 C2 C1 117.0(4) . . ?
O1 C6 C1 122.6(4) . . ?
O1 C6 C5 118.5(4) . . ?
C1 C6 C5 118.9(4) . . ?
N5 C34 C35 119.3(4) . . ?
N5 C34 C33 122.2(4) . 2_656 ?
C35 C34 C33 118.5(4) . 2_656 ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C6 C1 C2 122.5(4) . . ?
C6 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
N4 C25 C26 119.3(4) . . ?
N4 C25 C30 122.7(4) . . ?
C26 C25 C30 118.0(4) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N5 C33 C32 119.1(4) . . ?
N5 C33 C34 120.8(4) . 2_656 ?
C32 C33 C34 120.0(4) . 2_656 ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
N3 C30 C29 120.6(4) . . ?
N3 C30 C25 119.3(4) . . ?
C29 C30 C25 120.1(4) . . ?
N4 C24 C23 119.0(4) . . ?
N4 C24 C19 122.2(4) . . ?
C23 C24 C19 118.8(4) . . ?
N2 C13 C14 119.7(4) . . ?
N2 C13 C18 121.7(4) . . ?
C14 C13 C18 118.6(4) . . ?
N1 C18 C17 120.5(4) . . ?
N1 C18 C13 121.1(4) . . ?
C17 C18 C13 118.4(4) . . ?
C22 C23 C24 120.5(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C36 C35 C34 120.3(5) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 Cl01 120.3(4) . . ?
C6 C5 Cl01 120.0(4) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 Cl02 120.5(4) . . ?
C2 C3 Cl02 118.5(4) . . ?
C20 C21 C22 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C31 C32 C33 119.4(5) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C28 C29 C30 119.4(5) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C32 C31 C36 120.5(5) . 2_656 ?
C32 C31 H31 119.8 . . ?
C36 C31 H31 119.8 2_656 . ?
C35 C36 C31 121.3(4) . 2_656 ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 2_656 . ?
C29 C28 C27 121.9(5) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C26 C27 C28 119.9(5) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
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
Cl01 C5 1.743(5) . ?
Cl02 C3 1.741(5) . ?
O2 C2 1.338(5) . ?
O2 H2 0.8200 . ?
O1 C6 1.358(5) . ?
O1 H1 0.8200 . ?
N3 C19 1.347(6) . ?
N3 C30 1.363(5) . ?
N5 C34 1.356(6) . ?
N5 C33 1.357(5) . ?
N1 C18 1.344(6) . ?
N1 C7 1.361(6) . ?
N2 C13 1.343(6) . ?
N2 C12 1.348(5) . ?
N4 C24 1.344(5) . ?
N4 C25 1.345(6) . ?
C4 C5 1.378(6) . ?
C4 C3 1.387(6) . ?
C4 H4 0.9300 . ?
C19 C20 1.419(6) . ?
C19 C24 1.431(6) . ?
C7 C8 1.424(6) . ?
C7 C12 1.433(6) . ?
C12 C11 1.423(7) . ?
C2 C3 1.403(6) . ?
C2 C1 1.410(6) . ?
C6 C1 1.381(6) . ?
C6 C5 1.406(6) . ?
C34 C35 1.416(6) . ?
C34 C33 1.428(6) 2_656 ?
C20 C21 1.372(7) . ?
C20 H20 0.9300 . ?
C1 H1A 0.9300 . ?
C25 C26 1.425(6) . ?
C25 C30 1.446(6) . ?
C14 C15 1.351(7) . ?
C14 C13 1.430(6) . ?
C14 H14 0.9300 . ?
C33 C32 1.420(7) . ?
C8 C9 1.365(7) . ?
C8 H8 0.9300 . ?
C26 C27 1.360(7) . ?
C26 H26 0.9300 . ?
C30 C29 1.410(6) . ?
C24 C23 1.429(6) . ?
C13 C18 1.448(6) . ?
C18 C17 1.414(7) . ?
C23 C22 1.363(6) . ?
C23 H23 0.9300 . ?
C35 C36 1.363(7) . ?
C35 H35 0.9300 . ?
C17 C16 1.356(6) . ?
C17 H17 0.9300 . ?
C21 C22 1.429(7) . ?
C21 H21 0.9300 . ?
C15 C16 1.431(7) . ?
C15 H15 0.9300 . ?
C32 C31 1.372(7) . ?
C32 H32 0.9300 . ?
C29 C28 1.354(7) . ?
C29 H29 0.9300 . ?
C16 H16 0.9300 . ?
C11 C10 1.364(6) . ?
C11 H11 0.9300 . ?
C9 C10 1.405(7) . ?
C9 H9 0.9300 . ?
C31 C36 1.412(7) 2_656 ?
C31 H31 0.9300 . ?
C36 H36 0.9300 . ?
C28 C27 1.428(7) . ?
C28 H28 0.9300 . ?
C22 H22 0.9300 . ?
C10 H10 0.9300 . ?
C27 H27 0.9300 . ?
