Crystal structure of 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin monohydrate, C32H49N3O6S
Liu, Si-Jie; Fan, Yuan; Shang, Ruofeng; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 125–127; doi:10.1515/ncrs-2021-0403

data_8104978
_publ_section_title
;
 Crystal structure of
 14-O-[(4-(4-hydroxypiperidine-1-yl)-6-methylpyrimidine-2-yl)thioacetyl]-mutilin
 monohydrate, C32H49N3O6S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              125
_journal_page_last               127
_journal_paper_doi               10.1515/ncrs-2021-0403
_journal_volume                  237
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C32 H47 N3 O5 S, H2 O'
_chemical_formula_sum            'C32 H49 N3 O6 S'
_chemical_formula_weight         603.80
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2618(2)
_cell_length_b                   12.4066(2)
_cell_length_c                   27.2256(5)
_cell_measurement_reflns_used    3807
_cell_measurement_temperature    173.20(10)
_cell_measurement_theta_max      69.8430
_cell_measurement_theta_min      8.5730
_cell_volume                     3128.42(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2(Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL(Sheldrick, 2015) '
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -1.00  26.00   1.00    1.00    --    0.00  57.00 -90.00   27
  2  \w     44.00 120.00   1.00    1.00    --   54.00  57.00-150.00   76
  3  \w    153.00 178.00   1.00    5.00    --  108.00 111.00-120.00   25
  4  \w    101.00 174.00   1.00    5.00    --  108.00 111.00 -90.00   73
  5  \w    128.00 156.00   1.00    5.00    --  108.00 107.00 113.00   28
  6  \w     65.00 129.00   1.00    5.00    --  108.00 -38.00  90.00   64
  7  \w     52.00 178.00   1.00    5.00    --  108.00  12.00  60.00  126
  8  \w     47.00  80.00   1.00    5.00    --  108.00-111.00  60.00   33
  9  \w     16.00  62.00   1.00    1.00    --   54.00 -57.00  60.00   46
 10  \w    -18.00  75.00   1.00    1.00    --   54.00 -38.00 120.00   93
 11  \w    -37.00  29.00   1.00    1.00    --    0.00 -77.00  60.00   66
 12  \w    -70.00 -40.00   1.00    1.00    --    0.00 -77.00  60.00   30
 13  \w     33.00  79.00   1.00    1.00    --   54.00 -41.00-126.00   46
 14  \w     41.00  91.00   1.00    5.00    --  108.00 -77.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1402479000
_diffrn_orient_matrix_UB_12      0.0408175000
_diffrn_orient_matrix_UB_13      -0.0240720000
_diffrn_orient_matrix_UB_21      0.0477549000
_diffrn_orient_matrix_UB_22      -0.0488837000
_diffrn_orient_matrix_UB_23      -0.0493960000
_diffrn_orient_matrix_UB_31      -0.0756542000
_diffrn_orient_matrix_UB_32      -0.1066013000
_diffrn_orient_matrix_UB_33      0.0134771000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9661
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         3.916
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1773 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.036(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.327
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0517
_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/[\s^2^(Fo^2^)+(0.0644P)^2^+1.3742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1355
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                4775
_reflns_number_total             5241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0403_suppl.cif
_cod_data_source_block           exp_yuanf_1031
_cod_original_cell_volume        3128.42(12)
_cod_database_code               8104978
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.799
_reflns_odcompleteness_completeness 98.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H6-H10
 2 with sigma of 0.01
 H10-H6
 2.5 with sigma of 0.01
3.a Free rotating group:
 O6(H6A,H6B)
3.b Ternary CH refined with riding coordinates:
 C5(H5A), C6(H6), C8(H8), C10(H10), C18(H18), C30(H30)
3.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,
 H17B), C22(H22A,H22B), C28(H28A,H28B), C29(H29A,H29B), C31(H31A,H31B),
 C32(H32A,H32B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2A), C25(H25)
3.e Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C27(H27A,H27B,H27C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5)
;