Design, Synthesis, and Biological Evaluation of Novel Fused Spiro-4<i>H</i>-Pyran Derivatives as Bacterial Biofilm Disruptor.
Saigal, ?; Irfan, Mohammad; Khan, Parvez; Abid, Mohammad; Khan, Md Musawwer; ACS omega 4 (2019) 16794–16807; doi:10.1021/acsomega.9b01571

data_4516973
_publ_section_title
;
 Design, Synthesis, and Biological Evaluation of Novel Fused
 Spiro-4<i>H</i>-Pyran Derivatives as Bacterial Biofilm Disruptor.
;
_journal_issue                   16
_journal_name_full               'ACS omega'
_journal_page_first              16794
_journal_page_last               16807
_journal_paper_doi               10.1021/acsomega.9b01571
_journal_volume                  4
_journal_year                    2019
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C20 H21 N3 O5'
_chemical_formula_sum            'C20 H21 N3 O5'
_chemical_formula_weight         383.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.235(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7689(3)
_cell_length_b                   11.6234(3)
_cell_length_c                   13.7556(4)
_cell_measurement_reflns_used    14906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2160
_cell_measurement_theta_min      3.5090
_cell_volume                     1851.75(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_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    -78.00  -6.00   0.50   10.00    --   -9.95 -19.00  30.00  144
  2  \w    -48.00 -22.00   0.50   10.00    --   -9.95 125.00 -60.00   52
  3  \w    -74.00   6.00   0.50   10.00    --   -9.95 -77.00 150.00  160
  4  \w     40.00  72.00   0.50   10.00    --   10.22  57.00-150.00   64
  5  \w     23.00  59.00   0.50   10.00    --   10.22-125.00 150.00   72
  6  \w    -53.00  24.00   0.50   10.00    --   10.22 -57.00   0.00  154
  7  \w    -19.00  43.00   0.50   10.00    --   10.22 -99.00 -90.00  124
  8  \w     23.00  59.00   0.50   10.00    --   10.22-125.00   0.00   72
  9  \w      6.00  78.00   0.50   10.00    --   10.22  19.00   0.00  144
 10  \w    -30.00   4.00   0.50   10.00    --   10.22 112.00  56.84   68
 11  \w    -40.00  -9.00   0.50   10.00    --   10.22 129.00 162.54   62
 12  \w    -53.00  26.00   0.50   10.00    --   10.22 -77.00  60.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0295507000
_diffrn_orient_matrix_UB_12      -0.0169278000
_diffrn_orient_matrix_UB_13      -0.0473453000
_diffrn_orient_matrix_UB_21      0.0528702000
_diffrn_orient_matrix_UB_22      -0.0188794000
_diffrn_orient_matrix_UB_23      -0.0125263000
_diffrn_orient_matrix_UB_31      -0.0089000000
_diffrn_orient_matrix_UB_32      -0.0555158000
_diffrn_orient_matrix_UB_33      0.0186735000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.357
_diffrn_reflns_theta_min         3.483
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0443
_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/[\s^2^(Fo^2^)+(0.0684P)^2^+0.4183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3349
_reflns_number_total             3993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01571_si_002.cif
_cod_data_source_block           sub-musa-hrms
_cod_database_code               4516973
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_diffrn_oxdiff_ac3_digest_frames
;
019fb5ec463ba96462876829947365ec3000025b08c
;
_diffrn_oxdiff_ac3_digest_hkl
;
01c004ef00201ece620c0d2135e09f8acbcb15
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C13(H13), C16(H16), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C18(H18A,H18B,
 H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.694