#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:38:18 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296338 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/37/7133760.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_7133760
loop_
_publ_author_name
'Dillon, Alexandra M.'
'Shtukenberg, Alexander G.'
'Demkiw, Krystyna M.'
'Woerpel, K. A.'
'Ward, Michael D.'
_publ_section_title
;
 Hydrogen-bonded frameworks for conformational analysis of reactive
 substrates.
;
_journal_issue                   82
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              11770
_journal_page_last               11773
_journal_paper_doi               10.1039/d4cc03430a
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C21 H27 Br N6 O7 S2'
_chemical_formula_weight         619.51
_chemical_name_common            AD-II-143-A1
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-08-08 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.550(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7603(6)
_cell_length_b                   21.0415(17)
_cell_length_c                   7.9327(6)
_cell_measurement_reflns_used    9797
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.4399
_cell_measurement_theta_min      2.6048
_cell_volume                     1277.37(17)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Diamond (Brakdenburg 2014)'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 SMART APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3339
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              Incoatec
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.602
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0483
_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)+(0.0634P)²+2.0625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3217
_reflns_number_total             3339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03430a2.cif
_cod_data_source_block           23mdw66d
_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/RSC/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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133757--7133764.cif.
;
_cod_database_code               7133760
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.19302(8) 0.29445(6) 0.35982(7) 0.02694(16) Uani d . . . 1 . .
O O006 0.1048(5) 0.2176(2) 0.7507(5) 0.0182(8) Uani d . . . 1 . .
C C13 0.2553(7) 0.3798(2) 0.7302(7) 0.0187(10) Uani d . . D 1 . .
H H13 0.314738 0.377109 0.635001 0.022000 Uiso calc U . R 1 . .
C C14 0.2479(7) 0.4373(2) 0.8150(7) 0.0223(11) Uani d . . D 1 . .
H H14 0.302243 0.473852 0.776994 0.027000 Uiso calc U . R 1 . .
C C15 0.1618(8) 0.4417(3) 0.9546(7) 0.0251(12) Uani d . . D 1 . .
H H15 0.158976 0.480943 1.013445 0.030000 Uiso calc U . R 1 . .
C C16 0.0801(8) 0.3885(2) 1.0073(7) 0.0247(12) Uani d . . D 1 . .
H H16 0.019048 0.391492 1.101338 0.030000 Uiso calc U . R 1 . .
C C17 0.0868(7) 0.3305(2) 0.9235(6) 0.0179(10) Uani d . . D 1 . .
H H17 0.031165 0.294130 0.960703 0.021000 Uiso calc U . R 1 . .
C C18 0.1755(6) 0.3261(2) 0.7848(6) 0.0158(10) Uani d . . D 1 . .
C C19 0.1847(6) 0.2621(3) 0.7065(7) 0.0131(9) Uani d . . . 1 . .
C C20 0.3006(7) 0.2518(3) 0.5728(7) 0.0172(10) Uani d . . . 1 . .
H H20 0.416668 0.271868 0.614060 0.021000 Uiso calc U . R 1 . .
C C21 0.3309(5) 0.1788(2) 0.5335(6) 0.0080(8) Uani d . . . 1 . .
H H21A 0.369884 0.156148 0.640975 0.012000 Uiso calc U . R 1 . .
H H21B 0.420245 0.175236 0.460007 0.012000 Uiso calc U . R 1 . .
H H21C 0.221291 0.160180 0.475312 0.012000 Uiso calc U . R 1 . .
S S1 0.69560(16) 0.17048(6) 0.07203(17) 0.0143(2) Uani d . . . 1 . .
S S2 0.67464(15) 0.46736(6) 0.42273(17) 0.0138(2) Uani d . . . 1 . .
O O1 0.8361(5) 0.18162(19) -0.0256(5) 0.0170(8) Uani d . . . 1 . .
O O2 0.5238(5) 0.1768(2) -0.0341(5) 0.0194(8) Uani d . . . 1 . .
O O3 0.7161(5) 0.11016(19) 0.1648(5) 0.0189(8) Uani d . . . 1 . .
O O4 0.6471(5) 0.52731(19) 0.3308(6) 0.0199(8) Uani d . . . 1 . .
O O5 0.8487(5) 0.4635(2) 0.5283(5) 0.0184(8) Uani d . . . 1 . .
O O6 0.5364(5) 0.45392(19) 0.5222(5) 0.0167(7) Uani d . . . 1 . .
C C1 0.7094(6) 0.2304(2) 0.2299(6) 0.0116(9) Uani d . . . 1 . .
C C2 0.7417(7) 0.2128(3) 0.3979(7) 0.0143(10) Uani d . . . 1 . .
H H2 0.757834 0.169205 0.427081 0.017000 Uiso calc U . R 1 . .
C C3 0.7513(7) 0.2584(3) 0.5275(7) 0.0146(10) Uani d . . . 1 . .
H H3 0.774421 0.245379 0.643765 0.018000 Uiso calc U . R 1 . .
C C4 0.7277(7) 0.3216(3) 0.4884(7) 0.0134(9) Uani d . . . 1 . .
H H4 0.733629 0.352007 0.577710 0.016000 Uiso calc U . R 1 . .
C C5 0.6942(6) 0.3420(2) 0.3138(7) 0.0114(9) Uani d . . . 1 . .
C C6 0.6689(6) 0.4068(2) 0.2660(7) 0.0128(9) Uani d . . . 1 . .
C C7 0.6429(7) 0.4250(3) 0.0980(7) 0.0172(10) Uani d . . . 1 . .
H H7 0.627487 0.468707 0.069131 0.021000 Uiso calc U . R 1 . .
C C8 0.6389(7) 0.3799(3) -0.0301(7) 0.0188(11) Uani d . . . 1 . .
H H8 0.622920 0.393164 -0.146167 0.023000 Uiso calc U . R 1 . .
C C9 0.6576(7) 0.3163(3) 0.0083(7) 0.0159(10) Uani d . . . 1 . .
H H9 0.651485 0.285943 -0.081143 0.019000 Uiso calc U . R 1 . .
C C10 0.6864(5) 0.2956(3) 0.1827(6) 0.0102(8) Uani d . . . 1 . .
N N1 0.7975(6) 0.6405(2) 0.9299(6) 0.0167(9) Uani d . . . 1 . .
H H1A 0.899325 0.659560 0.955825 0.020000 Uiso calc U . R 1 . .
H H1B 0.705114 0.656309 0.966036 0.020000 Uiso calc U . R 1 . .
N N2 0.6285(6) 0.5589(2) 0.7988(6) 0.0190(9) Uani d . . . 1 . .
H H2A 0.618661 0.523819 0.737534 0.023000 Uiso calc U . R 1 . .
H H2B 0.536517 0.574871 0.835110 0.023000 Uiso calc U . R 1 . .
N N3 0.9208(6) 0.5635(2) 0.7814(7) 0.0191(9) Uani d . . . 1 . .
H H3A 1.023213 0.582283 0.806659 0.023000 Uiso calc U . R 1 . .
H H3B 0.909990 0.528618 0.719543 0.023000 Uiso calc U . R 1 . .
C C11 0.7831(7) 0.5879(3) 0.8366(7) 0.0142(9) Uani d . . . 1 . .
N N4 0.1711(6) 0.4956(2) 0.4056(7) 0.0175(9) Uani d . . . 1 . .
H H4A 0.274201 0.477138 0.424898 0.021000 Uiso calc U . R 1 . .
H H4B 0.078639 0.475516 0.429318 0.021000 Uiso calc U . R 1 . .
N N5 -0.0002(6) 0.5822(2) 0.3107(7) 0.0206(10) Uani d . . . 1 . .
H H5A -0.010397 0.620769 0.267472 0.025000 Uiso calc U . R 1 . .
H H5B -0.092934 0.562193 0.334312 0.025000 Uiso calc U . R 1 . .
N N6 0.2941(6) 0.5846(2) 0.3045(6) 0.0174(9) Uani d . . . 1 . .
H H6A 0.283114 0.623148 0.261247 0.021000 Uiso calc U . R 1 . .
H H6B 0.397322 0.566181 0.323898 0.021000 Uiso calc U . R 1 . .
C C12 0.1550(7) 0.5541(3) 0.3404(6) 0.0146(9) Uani d . . . 1 . .
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C14 C13 C18 . . 120.0(5) ?
C14 C13 H13 . . 120.000000 ?
C18 C13 H13 . . 120.000000 ?
C15 C14 C13 . . 120.5(5) ?
C15 C14 H14 . . 119.700000 ?
C13 C14 H14 . . 119.700000 ?
C16 C15 C14 . . 119.4(5) ?
C16 C15 H15 . . 120.300000 ?
C14 C15 H15 . . 120.300000 ?
C15 C16 C17 . . 120.5(5) ?
C15 C16 H16 . . 119.700000 ?
C17 C16 H16 . . 119.700000 ?
C18 C17 C16 . . 119.8(5) ?
C18 C17 H17 . . 120.100000 ?
C16 C17 H17 . . 120.100000 ?
C13 C18 C17 . . 119.7(5) ?
C13 C18 C19 . . 123.3(4) ?
C17 C18 C19 . . 116.9(4) ?
O006 C19 C18 . . 121.2(5) ?
O006 C19 C20 . . 119.0(5) ?
C18 C19 C20 . . 119.8(4) ?
C19 C20 C21 . . 113.6(4) ?
C19 C20 Br1 . . 108.5(4) ?
C21 C20 Br1 . . 109.1(3) ?
C19 C20 H20 . . 108.500000 ?
C21 C20 H20 . . 108.500000 ?
Br1 C20 H20 . . 108.500000 ?
C20 C21 H21A . . 109.500000 ?
C20 C21 H21B . . 109.500000 ?
H21A C21 H21B . . 109.500000 ?
C20 C21 H21C . . 109.500000 ?
H21A C21 H21C . . 109.500000 ?
H21B C21 H21C . . 109.500000 ?
O1 S1 O2 . . 111.8(2) ?
O1 S1 O3 . . 112.2(2) ?
O2 S1 O3 . . 112.4(2) ?
O1 S1 C1 . . 107.4(2) ?
O2 S1 C1 . . 106.6(2) ?
O3 S1 C1 . . 105.9(2) ?
O4 S2 O6 . . 112.2(2) ?
O4 S2 O5 . . 112.2(3) ?
O6 S2 O5 . . 111.7(2) ?
O4 S2 C6 . . 106.7(2) ?
O6 S2 C6 . . 107.7(2) ?
O5 S2 C6 . . 105.9(2) ?
C2 C1 C10 . . 120.7(5) ?
C2 C1 S1 . . 118.6(4) ?
C10 C1 S1 . . 120.7(4) ?
C1 C2 C3 . . 120.7(5) ?
C1 C2 H2 . . 119.600000 ?
C3 C2 H2 . . 119.600000 ?
C4 C3 C2 . . 120.6(5) ?
C4 C3 H3 . . 119.700000 ?
C2 C3 H3 . . 119.700000 ?
C3 C4 C5 . . 120.4(5) ?
C3 C4 H4 . . 119.800000 ?
C5 C4 H4 . . 119.800000 ?
C6 C5 C10 . . 118.5(5) ?
C6 C5 C4 . . 122.8(5) ?
C10 C5 C4 . . 118.7(5) ?
C7 C6 C5 . . 121.4(5) ?
C7 C6 S2 . . 117.5(4) ?
C5 C6 S2 . . 121.0(4) ?
C6 C7 C8 . . 120.2(5) ?
C6 C7 H7 . . 119.900000 ?
C8 C7 H7 . . 119.900000 ?
C9 C8 C7 . . 121.0(5) ?
C9 C8 H8 . . 119.500000 ?
C7 C8 H8 . . 119.500000 ?
C8 C9 C10 . . 120.3(5) ?
C8 C9 H9 . . 119.900000 ?
C10 C9 H9 . . 119.900000 ?
C5 C10 C1 . . 118.8(4) ?
C5 C10 C9 . . 118.6(5) ?
C1 C10 C9 . . 122.6(5) ?
C11 N1 H1A . . 120.000000 ?
C11 N1 H1B . . 120.000000 ?
H1A N1 H1B . . 120.000000 ?
C11 N2 H2A . . 120.000000 ?
C11 N2 H2B . . 120.000000 ?
H2A N2 H2B . . 120.000000 ?
C11 N3 H3A . . 120.000000 ?
C11 N3 H3B . . 120.000000 ?
H3A N3 H3B . . 120.000000 ?
N3 C11 N1 . . 120.7(5) ?
N3 C11 N2 . . 119.6(5) ?
N1 C11 N2 . . 119.7(5) ?
C12 N4 H4A . . 120.000000 ?
C12 N4 H4B . . 120.000000 ?
H4A N4 H4B . . 120.000000 ?
C12 N5 H5A . . 120.000000 ?
C12 N5 H5B . . 120.000000 ?
H5A N5 H5B . . 120.000000 ?
C12 N6 H6A . . 120.000000 ?
C12 N6 H6B . . 120.000000 ?
H6A N6 H6B . . 120.000000 ?
N6 C12 N5 . . 119.6(5) ?
N6 C12 N4 . . 120.1(5) ?
N5 C12 N4 . . 120.2(5) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C20 . 1.973(6) ?
O006 C19 . 1.207(7) ?
C13 C14 . 1.390(4) ?
C13 C18 . 1.390(4) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.388(5) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.386(5) ?
C15 H15 . 0.950000 ?
C16 C17 . 1.394(4) ?
C16 H16 . 0.950000 ?
C17 C18 . 1.394(4) ?
C17 H17 . 0.950000 ?
C18 C19 . 1.490(7) ?
C19 C20 . 1.515(7) ?
C20 C21 . 1.591(7) ?
C20 H20 . 1.000000 ?
C21 H21A . 0.980000 ?
C21 H21B . 0.980000 ?
C21 H21C . 0.980000 ?
S1 O1 . 1.457(4) ?
S1 O2 . 1.460(4) ?
S1 O3 . 1.463(4) ?
S1 C1 . 1.767(5) ?
S2 O4 . 1.455(4) ?
S2 O6 . 1.461(4) ?
S2 O5 . 1.469(4) ?
S2 C6 . 1.777(5) ?
C1 C2 . 1.366(7) ?
C1 C10 . 1.425(7) ?
C2 C3 . 1.398(7) ?
C2 H2 . 0.950000 ?
C3 C4 . 1.371(7) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.433(7) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.419(7) ?
C5 C10 . 1.421(7) ?
C6 C7 . 1.369(8) ?
C7 C8 . 1.387(8) ?
C7 H7 . 0.950000 ?
C8 C9 . 1.376(8) ?
C8 H8 . 0.950000 ?
C9 C10 . 1.432(7) ?
C9 H9 . 0.950000 ?
N1 C11 . 1.326(7) ?
N1 H1A . 0.880000 ?
N1 H1B . 0.880000 ?
N2 C11 . 1.334(7) ?
N2 H2A . 0.880000 ?
N2 H2B . 0.880000 ?
N3 C11 . 1.323(7) ?
N3 H3A . 0.880000 ?
N3 H3B . 0.880000 ?
N4 C12 . 1.333(7) ?
N4 H4A . 0.880000 ?
N4 H4B . 0.880000 ?
N5 C12 . 1.327(7) ?
N5 H5A . 0.880000 ?
N5 H5B . 0.880000 ?
N6 C12 . 1.326(7) ?
N6 H6A . 0.880000 ?
N6 H6B . 0.880000 ?
