#------------------------------------------------------------------------------
#$Date: 2021-03-05 20:43:22 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262771 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560071.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_1560071
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            'C28 H22 Cl2 N2 O2'
_chemical_formula_weight         489.37
_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                94.129(7)
_cell_angle_beta                 94.866(7)
_cell_angle_gamma                98.239(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8453(13)
_cell_length_b                   10.4891(15)
_cell_length_c                   12.6940(19)
_cell_measurement_reflns_used    10718
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.2
_cell_volume                     1157.1(3)
_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 0.998
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12258
_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         27.484
_diffrn_reflns_theta_min         3.223
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       Prism
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0838P)²+0.2470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4119
_reflns_number_total             5291
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yc5029.cif
_cod_data_source_block           31CRES-DMP-PYR
_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               1560071
_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   0.941
_shelx_estimated_absorpt_t_max   0.941
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 1.02959(6) 0.68667(6) 0.08882(4) 0.03253(16) Uani 1 1 d . . . . .
Cl02 Cl 1.11357(6) 0.23705(5) 0.24945(4) 0.03074(16) Uani 1 1 d . . . . .
O2 O 0.93694(17) 0.32455(14) 0.41690(12) 0.0285(3) Uani 1 1 d . . . . .
H2 H 0.859281 0.332969 0.446050 0.043 Uiso 1 1 calc R U . . .
O1 O 0.84868(17) 0.72004(15) 0.26951(13) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.787264 0.719435 0.314426 0.044 Uiso 1 1 calc R U . . .
N1 N 0.66632(19) 0.34726(16) 0.50690(13) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.39818(19) 0.30727(16) 0.60654(13) 0.0214(4) Uani 1 1 d . . . . .
C24 C 0.5297(2) 0.32823(18) 0.44994(16) 0.0211(4) Uani 1 1 d . . . . .
C27 C 0.5353(2) 0.32621(18) 0.66345(16) 0.0207(4) Uani 1 1 d . . . . .
C26 C 0.6687(2) 0.34588(19) 0.61191(16) 0.0212(4) Uani 1 1 d . . . . .
H26 H 0.763077 0.358546 0.652424 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9548(2) 0.41021(19) 0.34255(16) 0.0220(4) Uani 1 1 d . . . . .
C22 C 0.4328(2) -0.01332(18) 0.46247(16) 0.0216(4) Uani 1 1 d . . . . .
C4 C 1.0627(2) 0.4679(2) 0.18094(16) 0.0252(5) Uani 1 1 d . . . . .
H4 H 1.121591 0.450104 0.125941 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9108(2) 0.6100(2) 0.26842(16) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.5053(2) 0.0681(2) 0.01210(15) 0.0236(4) Uani 1 1 d . . . . .
C3 C 1.0399(2) 0.3818(2) 0.25794(17) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.9981(2) 0.5796(2) 0.18580(16) 0.0239(4) Uani 1 1 d . . . . .
C25 C 0.3962(2) 0.30791(19) 0.50115(16) 0.0232(4) Uani 1 1 d . . . . .
H25 H 0.301945 0.294239 0.460407 0.028 Uiso 1 1 calc R U . . .
C1 C 0.8940(2) 0.5248(2) 0.34687(16) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.840331 0.545386 0.404086 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5253(3) 0.3302(2) 0.33194(16) 0.0272(5) Uani 1 1 d . . . . .
H23A H 0.552130 0.417458 0.314233 0.041 Uiso 1 1 calc R U . . .
H23B H 0.423828 0.296163 0.300171 0.041 Uiso 1 1 calc R U . . .
H23C H 0.597139 0.278119 0.305729 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3727(3) 0.1291(2) 0.00019(17) 0.0289(5) Uani 1 1 d . . . . .
C17 C 0.4491(3) -0.01394(19) 0.35222(17) 0.0263(5) Uani 1 1 d . . . . .
C15 C 0.7259(3) 0.0354(2) 0.38824(18) 0.0295(5) Uani 1 1 d . . . . .
H15 H 0.822237 0.050610 0.363411 0.035 Uiso 1 1 calc R U . . .
C28 C 0.5403(3) 0.3277(2) 0.78120(17) 0.0292(5) Uani 1 1 d . . . . .
H28A H 0.507648 0.405628 0.809350 0.044 Uiso 1 1 calc R U . . .
H28B H 0.643272 0.324378 0.810329 0.044 Uiso 1 1 calc R U . . .
H28C H 0.473176 0.254202 0.799760 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1564(3) -0.0670(2) 0.42490(19) 0.0309(5) Uani 1 1 d . . . . .
H20 H 0.059246 -0.086203 0.447883 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6502(2) 0.1428(2) 0.04835(16) 0.0280(5) Uani 1 1 d . . . . .
C16 C 0.6004(3) 0.0107(2) 0.31812(18) 0.0287(5) Uani 1 1 d . . . . .
H16 H 0.611820 0.009630 0.245921 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2854(2) -0.03872(18) 0.49956(17) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.7712(3) -0.0503(3) 0.03708(19) 0.0359(6) Uani 1 1 d . . . . .
H7 H 0.859079 -0.089127 0.045646 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6580(3) 0.2758(2) 0.07180(18) 0.0361(6) Uani 1 1 d . . . . .
H10 H 0.751888 0.325325 0.096226 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1722(3) -0.0667(2) 0.3173(2) 0.0328(5) Uani 1 1 d . . . . .
H19 H 0.085368 -0.084739 0.268892 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3157(3) -0.0398(2) 0.28101(18) 0.0295(5) Uani 1 1 d . . . . .
H18 H 0.323884 -0.038831 0.208505 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7821(3) 0.0782(3) 0.05991(18) 0.0346(5) Uani 1 1 d . . . . .
H8 H 0.877172 0.126070 0.083677 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3877(3) 0.2629(2) 0.02408(18) 0.0375(6) Uani 1 1 d . . . . .
H12 H 0.301626 0.304159 0.016175 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5291(3) 0.3348(2) 0.05935(18) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.536959 0.423676 0.074749 0.049 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 . . ?
C26 N1 C24 117.85(17) . . ?
C25 N2 C27 117.60(17) . . ?
N1 C24 C25 119.68(18) . . ?
N1 C24 C23 118.42(18) . . ?
C25 C24 C23 121.90(18) . . ?
N2 C27 C26 119.64(18) . . ?
N2 C27 C28 118.54(18) . . ?
C26 C27 C28 121.81(19) . . ?
N1 C26 C27 122.63(18) . . ?
N1 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
O2 C2 C1 122.99(18) . . ?
O2 C2 C3 118.29(18) . . ?
C1 C2 C3 118.71(19) . . ?
C17 C22 C21 120.72(19) . . ?
C17 C22 C22 119.6(2) . 2_656 ?
C21 C22 C22 119.7(2) . 2_656 ?
C5 C4 C3 120.02(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C6 C1 122.95(18) . . ?
O1 C6 C5 119.27(18) . . ?
C1 C6 C5 117.78(19) . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 C14 120.4(2) . 2_655 ?
C9 C14 C14 119.6(2) . 2_655 ?
C4 C3 C2 120.07(19) . . ?
C4 C3 Cl02 120.46(16) . . ?
C2 C3 Cl02 119.46(16) . . ?
C4 C5 C6 121.31(19) . . ?
C4 C5 Cl01 119.12(16) . . ?
C6 C5 Cl01 119.55(17) . . ?
N2 C25 C24 122.61(18) . . ?
N2 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C2 C1 C6 122.03(19) . . ?
C2 C1 H1A 119.0 . . ?
C6 C1 H1A 119.0 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 C7 123.0(2) . 2_655 ?
C14 C13 C7 118.2(2) . 2_655 ?
C18 C17 C22 118.3(2) . . ?
C18 C17 C16 122.9(2) . . ?
C22 C17 C16 118.9(2) . . ?
C16 C15 C21 121.5(2) . 2_656 ?
C16 C15 H15 119.2 . . ?
C21 C15 H15 119.2 2_656 . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C10 C9 C14 118.8(2) . . ?
C10 C9 C8 122.6(2) . . ?
C14 C9 C8 118.6(2) . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 C15 122.5(2) . 2_656 ?
C22 C21 C15 118.84(19) . 2_656 ?
C8 C7 C13 121.7(2) . 2_655 ?
C8 C7 H7 119.1 . . ?
C13 C7 H7 119.1 2_655 . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
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 1.738(2) . ?
Cl02 C3 1.736(2) . ?
O2 C2 1.353(2) . ?
O2 H2 0.8200 . ?
O1 C6 1.347(2) . ?
O1 H1 0.8200 . ?
N1 C26 1.333(3) . ?
N1 C24 1.336(3) . ?
N2 C25 1.337(3) . ?
N2 C27 1.339(3) . ?
C24 C25 1.393(3) . ?
C24 C23 1.497(3) . ?
C27 C26 1.394(3) . ?
C27 C28 1.490(3) . ?
C26 H26 0.9300 . ?
C2 C1 1.385(3) . ?
C2 C3 1.402(3) . ?
C22 C17 1.419(3) . ?
C22 C21 1.419(3) . ?
C22 C22 1.440(4) 2_656 ?
C4 C5 1.375(3) . ?
C4 C3 1.385(3) . ?
C4 H4 0.9300 . ?
C6 C1 1.388(3) . ?
C6 C5 1.399(3) . ?
C14 C13 1.416(3) . ?
C14 C9 1.424(3) . ?
C14 C14 1.428(4) 2_655 ?
C25 H25 0.9300 . ?
C1 H1A 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C13 C12 1.400(3) . ?
C13 C7 1.438(3) 2_655 ?
C17 C18 1.405(3) . ?
C17 C16 1.435(3) . ?
C15 C16 1.345(3) . ?
C15 C21 1.434(3) 2_656 ?
C15 H15 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C20 C19 1.384(3) . ?
C20 C21 1.403(3) . ?
C20 H20 0.9300 . ?
C9 C10 1.396(3) . ?
C9 C8 1.433(3) . ?
C16 H16 0.9300 . ?
C7 C8 1.346(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C19 C18 1.386(3) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C12 C11 1.385(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
