Synthetic, mechanistic and kinetic studies on the organo-nanocatalyzed synthesis of oxygen and nitrogen containing spiro compounds under ultrasonic conditions
Singh, Nongthombam Geetmani; Lily, Makroni; Devi, Shougaijam Premila; Rahman, Noimur; Ahmed, Aziz; Chandra, Asit K.; Nongkhlaw, Rishanlang; Green Chem. 18 (2016) 4216–; doi:10.1039/C6GC00724D

data_7225078
_publ_section_title
;
 Synthetic, mechanistic and kinetic studies on the organo-nanocatalyzed
 synthesis of oxygen and nitrogen containing spiro compounds under
 ultrasonic conditions
;
_journal_issue                   15
_journal_name_full               'Green Chem.'
_journal_page_first              4216
_journal_paper_doi               10.1039/C6GC00724D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H11 N3 O4'
_chemical_formula_sum            'C20 H11 N3 O4'
_chemical_formula_weight         357.33
_chemical_name_common            Spirooxindole
_chemical_name_systematic
2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-12-21 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                75.239(15)
_cell_angle_beta                 84.652(14)
_cell_angle_gamma                69.915(14)
_cell_formula_units_Z            4
_cell_length_a                   10.3603(15)
_cell_length_b                   13.054(2)
_cell_length_c                   14.655(3)
_cell_measurement_reflns_used    1724
_cell_measurement_temperature    291.6(2)
_cell_measurement_theta_max      23.5480
_cell_measurement_theta_min      3.5750
_cell_volume                     1800.0(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  1  \w     -6.00  90.00   1.00    7.56    --   19.62  37.00  30.00   96
  2  \w    -24.00  19.00   1.00    7.56    --  -17.43 -99.00-150.00   43
  3  \w    -24.00  22.00   1.00    7.56    --  -17.43 -99.00  30.00   46
  4  \w     35.00  95.00   1.00    7.56    --   19.62-178.00-120.00   60
  5  \w    -34.00  63.00   1.00    7.56    --   19.62 -19.00-180.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066617000
_diffrn_orient_matrix_UB_12      -0.0058535000
_diffrn_orient_matrix_UB_13      -0.0459763000
_diffrn_orient_matrix_UB_21      -0.0671020000
_diffrn_orient_matrix_UB_22      0.0400926000
_diffrn_orient_matrix_UB_23      -0.0031560000
_diffrn_orient_matrix_UB_31      0.0276951000
_diffrn_orient_matrix_UB_32      0.0436702000
_diffrn_orient_matrix_UB_33      -0.0195327000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12261
_diffrn_reflns_theta_full        29.0572
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3185
_exptl_crystal_description       plate
_exptl_crystal_F_000             736.4006
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.7403
_refine_diff_density_min         -0.5885
_refine_diff_density_rms         0.1454
_refine_ls_d_res_high            0.7317
_refine_ls_d_res_low             6.1367
_refine_ls_goodness_of_fit_ref   0.9953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9953
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.0942
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1280P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.2954
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3683
_reflns_number_total             8117
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6gc00724d2.cif
_cod_data_source_block           NGS-3B
_cod_depositor_comments
;
Adding full bibliography for 7225077--7225078.cif

2017-03-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1799.9(6)
_cod_original_formula_moiety     '2(C20 H11 N3 O4)'
_cod_original_formula_sum        'C40 H22 N6 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     714.66
_cod_database_code               7225078
_chemical_oxdiff_formula         C20H11N3O4
_reflns_odcompleteness_completeness 99.27
_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 N(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(Ha,Hb), N6(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H17), C24(H1ba), C25(H1o), C26(H1h), C36(H1s), C37(H1n), C38(H1u),
 C39(H1j), C6(H1g), C5(H1i), C4(H1l), C3(H15), C16(H1p), C17(H1q), C18(H1t),
 C19(H1c), N1(H4), N4(H5)
;
_olex2_date_sample_data_collection 2015-12-11
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.787