Spiro-condensation of 5-methoxycarbonyl-1H-pyrrole-2,3-diones with cyclic enoles to form spiro substituted furo[3,2-c]-coumarins and quinolines
Dubovtsev, Alexey Yu.; Silaichev, Pavel S.; Nazarov, Mikhail A.; Dmitriev, Maksim V.; Maslivets, Andrey N.; Rubin, Michael; RSC Adv. 6 (2016) 84730–; doi:10.1039/C6RA16889B

data_7226486
_publ_section_title
;
 Spiro-condensation of 5-methoxycarbonyl-1H-pyrrole-2,3-diones with cyclic
 enoles to form spiro substituted furo[3,2-c]-coumarins and quinolines
;
_journal_issue                   88
_journal_name_full               'RSC Adv.'
_journal_page_first              84730
_journal_paper_doi               10.1039/C6RA16889B
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C29 H20 N2 O6, C2 H3 N'
_chemical_formula_sum            'C31 H23 N3 O6'
_chemical_formula_weight         533.52
_chemical_melting_point          531.0(10)
_chemical_name_systematic
3'-Benzoyl-4'-hydroxy-5-methyl-1'-(4-tolyl)-2H-spiro?[furo?[3,2-c]quinoline-3,2'-pyrrole]-2,4,5'(1'H,5H)-trione
_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_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-06-18 deposited with the CCDC.
2016-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                83.352(10)
_cell_angle_beta                 74.653(13)
_cell_angle_gamma                89.492(11)
_cell_formula_units_Z            2
_cell_length_a                   10.0480(16)
_cell_length_b                   10.5278(12)
_cell_length_c                   13.3170(16)
_cell_measurement_reflns_used    3383
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      28.7140
_cell_measurement_theta_min      3.8190
_cell_volume                     1349.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details
;
  1 omega   31.00   75.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       14.0072   38.0000  -90.0000 44

  2 omega   -7.00   26.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -99.0000    0.0000 33

  3 omega  -85.00    4.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -38.0000    0.0000 89

  4 omega  -47.00   40.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541   57.0000 -180.0000 87

  5 omega  -94.00  -58.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -38.0000   90.0000 36

  6 omega -106.00  -36.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541 -178.0000 -150.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0299994000
_diffrn_orient_matrix_UB_12      0.0011888000
_diffrn_orient_matrix_UB_13      -0.0426841000
_diffrn_orient_matrix_UB_21      -0.0665709000
_diffrn_orient_matrix_UB_22      0.0033047000
_diffrn_orient_matrix_UB_23      0.0348596000
_diffrn_orient_matrix_UB_31      0.0054392000
_diffrn_orient_matrix_UB_32      0.0677569000
_diffrn_orient_matrix_UB_33      -0.0075017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12089
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.233
_diffrn_reflns_theta_min         2.834
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             556
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6306
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0650P)^2^+0.1775P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4550
_reflns_number_total             6306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra16889b2.cif
_cod_data_source_block           psu-339-da-209
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '530-532' was changed to '531.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_database_code               7226486
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N1SA, N1SB, C1SB, C2SB, C1SA, C2SA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Uiso/Uaniso restraints and constraints
N1SA \\sim N1SB \\sim C1SB \\sim C2SB \\sim C1SA \\sim C2SA: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
4. Same fragment restrains
{N1SA, C1SA, C2SA} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1SB, C1SB, C2SB}
5. Others
 Fixed Sof: N1SA(0.5) C1SA(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) C2SA(0.5)
 N1SB(0.5) C1SB(0.5) H1SD(0.5) H1SE(0.5) H1SF(0.5) C2SB(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28)
6.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C1SA(H1SA,H1SB,H1SC), C1SB(H1SD,
 H1SE,H1SF)
;
_shelx_res_checksum              58139
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method acetonitrile