#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:26:25 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/16/1571675.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_1571675
loop_
_publ_author_name
'Rehman, Zainab'
'Lubay, Jairah'
'Franks, W. Trent'
'Bartók, Albert P'
'Corlett, Emily K.'
'Nguyen, Bao'
'Scrivens, Garry'
'Samas, Brian M.'
'Frericks-Schmidt, Heather'
'Brown, Steven P.'
_publ_section_title
;
 Organic NMR crystallography: enabling progress for applications to
 pharmaceuticals and plant cell walls.
;
_journal_issue                   0
_journal_name_full               'Faraday discussions'
_journal_page_first              222
_journal_page_last               243
_journal_paper_doi               10.1039/d4fd00088a
_journal_volume                  255
_journal_year                    2025
_chemical_formula_sum            'C22 H27 N5 O4 S'
_chemical_formula_weight         457.55
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-04-29 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.013(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.1890(4)
_cell_length_b                   12.6757(6)
_cell_length_c                   10.9694(5)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      44.59
_cell_measurement_theta_min      4.41
_cell_volume                     1167.10(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15363
_diffrn_reflns_theta_full        44.59
_diffrn_reflns_theta_max         44.59
_diffrn_reflns_theta_min         4.41
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_correction_T_min  0.8358
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0556
_refine_ls_wR_factor_ref         0.0561
_reflns_number_gt                1798
_reflns_number_total             1846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4fd00088a2.cif
_cod_data_source_block           z501
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' 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 1571675.cif.
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1571675
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H4X H 0.938(2) 0.970(2) 0.222(2) 0.042(8) Uiso 1 1 d D . .
H3X H 0.535(4) 1.004(2) 0.171(3) 0.082(12) Uiso 1 1 d D . .
S1 S 0.31353(8) 0.99017(6) 0.29621(7) 0.0385(3) Uani 1 1 d . . .
N1 N 0.7270(3) 1.2594(2) -0.0658(3) 0.0444(7) Uani 1 1 d D . .
N2 N 0.5150(3) 1.2052(2) -0.0055(3) 0.0507(7) Uani 1 1 d . . .
N3 N 0.5843(3) 1.0544(2) 0.1344(2) 0.0367(6) Uani 1 1 d D . .
N4 N 0.8294(3) 0.96834(18) 0.2119(2) 0.0349(6) Uani 1 1 d D . .
N5 N 0.8357(3) 0.6853(2) 0.2984(2) 0.0414(7) Uani 1 1 d . . .
O1 O 0.8714(3) 0.59800(18) 0.1342(3) 0.0650(6) Uani 1 1 d . . .
O2 O 0.1594(2) 0.94155(16) 0.2588(2) 0.0566(6) Uani 1 1 d . . .
O3 O 0.3117(2) 1.10279(16) 0.28001(19) 0.0555(6) Uani 1 1 d . . .
O4 O 0.4028(2) 0.93681(15) 0.22910(17) 0.0392(5) Uani 1 1 d . . .
C1 C 0.8797(4) 1.2271(3) -0.0356(3) 0.0540(9) Uani 1 1 d . . .
H1 H 0.9483 1.2579 -0.0685 0.065 Uiso 1 1 calc R . .
C2 C 0.9171(4) 1.1437(2) 0.0489(3) 0.0489(9) Uani 1 1 d . . .
H2 H 1.0132 1.1073 0.0838 0.059 Uiso 1 1 calc R . .
C3 C 0.7798(3) 1.1235(2) 0.0730(3) 0.0334(7) Uani 1 1 d . . .
C4 C 0.6652(3) 1.1970(3) 0.0000(3) 0.0367(8) Uani 1 1 d . . .
C5 C 0.4823(4) 1.1320(3) 0.0624(3) 0.0500(9) Uani 1 1 d . . .
H5 H 0.3809 1.1324 0.0620 0.060 Uiso 1 1 calc R . .
C6 C 0.7353(4) 1.0468(2) 0.1428(3) 0.0312(7) Uani 1 1 d . . .
C7 C 0.7798(3) 0.8751(2) 0.2640(3) 0.0340(8) Uani 1 1 d . . .
H7 H 0.6671 0.8614 0.2084 0.041 Uiso 1 1 calc R . .
C8 C 0.8007(4) 0.8851(2) 0.4073(3) 0.0458(8) Uani 1 1 d . . .
H8A H 0.7363 0.9429 0.4159 0.055 Uiso 1 1 calc R . .
H8B H 0.9114 0.8999 0.4641 0.055 Uiso 1 1 calc R . .
C9 C 0.7499(4) 0.7825(3) 0.4499(3) 0.0592(10) Uani 1 1 d . . .
H9A H 0.6371 0.7715 0.3968 0.071 Uiso 1 1 calc R . .
H9B H 0.7654 0.7883 0.5426 0.071 Uiso 1 1 calc R . .
C10 C 0.8421(4) 0.6871(3) 0.4344(3) 0.0536(9) Uani 1 1 d . . .
H10 H 0.7877 0.6237 0.4455 0.064 Uiso 1 1 calc R . .
C11 C 1.0133(5) 0.6825(3) 0.5375(4) 0.0924(13) Uani 1 1 d . . .
H11A H 1.0634 0.6198 0.5239 0.139 Uiso 1 1 calc R . .
H11B H 1.0144 0.6813 0.6254 0.139 Uiso 1 1 calc R . .
H11C H 1.0701 0.7434 0.5284 0.139 Uiso 1 1 calc R . .
C12 C 0.8768(4) 0.7832(2) 0.2501(3) 0.0431(8) Uani 1 1 d . . .
H12A H 0.8582 0.7750 0.1570 0.052 Uiso 1 1 calc R . .
H12B H 0.9892 0.7979 0.3002 0.052 Uiso 1 1 calc R . .
C13 C 0.8351(3) 0.5971(3) 0.2298(4) 0.0459(8) Uani 1 1 d . . .
C14 C 0.7834(4) 0.4975(4) 0.2690(4) 0.0697(10) Uani 1 1 d . . .
H14 H 0.7368 0.4996 0.3300 0.084 Uiso 1 1 calc R . .
C15 C 0.8003(6) 0.4079(4) 0.2219(5) 0.1079(16) Uani 1 1 d . . .
H15A H 0.8466 0.4043 0.1607 0.129 Uiso 1 1 calc R . .
H15B H 0.7663 0.3466 0.2488 0.129 Uiso 1 1 calc R . .
C16 C 0.4126(4) 0.8649(3) 0.5167(4) 0.0512(9) Uani 1 1 d . . .
H16 H 0.3381 0.8165 0.4628 0.061 Uiso 1 1 calc R . .
C17 C 0.5103(5) 0.8381(3) 0.6454(4) 0.0620(10) Uani 1 1 d . . .
H17 H 0.5016 0.7714 0.6771 0.074 Uiso 1 1 calc R . .
C18 C 0.6200(5) 0.9076(4) 0.7279(4) 0.0642(10) Uani 1 1 d . . .
C19 C 0.7289(6) 0.8763(4) 0.8678(4) 0.1083(15) Uani 1 1 d . . .
H19A H 0.8212 0.9210 0.8992 0.162 Uiso 1 1 calc R . .
H19B H 0.7614 0.8042 0.8684 0.162 Uiso 1 1 calc R . .
H19C H 0.6737 0.8836 0.9251 0.162 Uiso 1 1 calc R . .
C20 C 0.6300(5) 1.0065(3) 0.6786(4) 0.0726(11) Uani 1 1 d . . .
H20 H 0.7036 1.0551 0.7331 0.087 Uiso 1 1 calc R . .
C21 C 0.5307(4) 1.0339(3) 0.5481(4) 0.0559(9) Uani 1 1 d . . .
H21 H 0.5373 1.1011 0.5166 0.067 Uiso 1 1 calc R . .
C22 C 0.4242(3) 0.9634(2) 0.4662(3) 0.0378(8) Uani 1 1 d . . .
H1X H 0.674(4) 1.319(2) -0.126(3) 0.072(11) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O3 S1 O2 115.38(11) . . ?
O3 S1 O4 112.04(11) . . ?
O2 S1 O4 110.12(12) . . ?
O3 S1 C22 107.19(13) . . ?
O2 S1 C22 107.29(13) . . ?
O4 S1 C22 104.04(11) . . ?
C4 N1 C1 108.0(2) . . ?
C5 N2 C4 112.8(2) . . ?
C6 N3 C5 122.3(3) . . ?
C6 N4 C7 126.3(2) . . ?
C13 N5 C12 116.5(2) . . ?
C13 N5 C10 124.7(3) . . ?
C12 N5 C10 116.6(3) . . ?
C2 C1 N1 110.4(3) . . ?
C1 C2 C3 105.8(3) . . ?
C4 C3 C6 117.4(3) . . ?
C4 C3 C2 107.1(3) . . ?
C6 C3 C2 135.3(3) . . ?
N1 C4 N2 125.1(3) . . ?
N1 C4 C3 108.6(2) . . ?
N2 C4 C3 126.4(3) . . ?
N2 C5 N3 125.5(3) . . ?
N4 C6 N3 120.1(3) . . ?
N4 C6 C3 124.4(3) . . ?
N3 C6 C3 115.6(3) . . ?
N4 C7 C8 114.2(2) . . ?
N4 C7 C12 107.0(2) . . ?
C8 C7 C12 109.9(2) . . ?
C7 C8 C9 108.9(2) . . ?
C8 C9 C10 113.0(2) . . ?
N5 C10 C11 110.9(3) . . ?
N5 C10 C9 109.3(3) . . ?
C11 C10 C9 113.7(3) . . ?
N5 C12 C7 111.6(2) . . ?
O1 C13 N5 122.0(3) . . ?
O1 C13 C14 119.4(3) . . ?
N5 C13 C14 118.5(3) . . ?
C15 C14 C13 122.3(4) . . ?
C17 C16 C22 120.6(3) . . ?
C18 C17 C16 121.3(3) . . ?
C17 C18 C20 118.2(3) . . ?
C17 C18 C19 120.7(4) . . ?
C20 C18 C19 121.0(4) . . ?
C18 C20 C21 120.6(4) . . ?
C22 C21 C20 120.6(3) . . ?
C21 C22 C16 118.7(3) . . ?
C21 C22 S1 121.6(3) . . ?
C16 C22 S1 119.5(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
S1 O3 1.438(2) . ?
S1 O2 1.4422(19) . ?
S1 O4 1.4713(19) . ?
S1 C22 1.756(3) . ?
N1 C4 1.343(4) . ?
N1 C1 1.367(4) . ?
N2 C5 1.299(4) . ?
N2 C4 1.361(4) . ?
N3 C6 1.356(3) . ?
N3 C5 1.366(4) . ?
N4 C6 1.333(3) . ?
N4 C7 1.464(4) . ?
N5 C13 1.347(4) . ?
N5 C12 1.458(4) . ?
N5 C10 1.469(4) . ?
O1 C13 1.223(4) . ?
C1 C2 1.354(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.390(4) . ?
C3 C6 1.398(4) . ?
C7 C8 1.510(4) . ?
C7 C12 1.512(4) . ?
C8 C9 1.519(4) . ?
C9 C10 1.525(4) . ?
C10 C11 1.520(5) . ?
C13 C14 1.474(5) . ?
C14 C15 1.283(5) . ?
C16 C17 1.372(5) . ?
C16 C22 1.388(4) . ?
C17 C18 1.367(5) . ?
C18 C20 1.383(5) . ?
C18 C19 1.505(5) . ?
C20 C21 1.393(5) . ?
C21 C22 1.359(4) . ?
