A rearrangement involving a solid-state melt reaction for the synthesis of multifunctional tetrasubstituted olefins.
Bakthadoss, Manickam; Raman, Selvakumar; Mushaf, Mohammad; Organic & biomolecular chemistry 17 (2019) 4767–4773; doi:10.1039/c9ob00639g

data_7156800
_publ_section_title
;
 A rearrangement involving a solid-state melt reaction for the synthesis
 of multifunctional tetrasubstituted olefins.
;
_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4767
_journal_page_last               4773
_journal_paper_doi               10.1039/c9ob00639g
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         '0.57(C23 H17 N3 O)'
_chemical_formula_sum            'C13 H14 N2 O0.07'
_chemical_formula_weight         199.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-02
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_audit_update_record
;
2019-03-02 deposited with the CCDC.    2019-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            14
_cell_length_a                   20.4023(13)
_cell_length_b                   16.0765(13)
_cell_length_c                   11.2547(7)
_cell_measurement_reflns_used    2798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1158
_cell_measurement_theta_min      2.9720
_cell_volume                     3691.5(4)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
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'CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET) (compiled Sep 14 2012,17:21:16)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
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_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_UB_11      -0.0170780000
_diffrn_orient_matrix_UB_12      -0.0154059000
_diffrn_orient_matrix_UB_13      0.0502308000
_diffrn_orient_matrix_UB_21      -0.0202922000
_diffrn_orient_matrix_UB_22      -0.0241638000
_diffrn_orient_matrix_UB_23      -0.0378252000
_diffrn_orient_matrix_UB_31      0.0224634000
_diffrn_orient_matrix_UB_32      -0.0335670000
_diffrn_orient_matrix_UB_33      0.0041253000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0538
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_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10778
_diffrn_reflns_point_group_measured_fraction_full 0.767
_diffrn_reflns_point_group_measured_fraction_max 0.637
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.180
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
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    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             1492
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 968 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.414
_reflns_Friedel_fraction_full    0.510
_reflns_Friedel_fraction_max     0.393
_reflns_number_gt                3993
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00639g2.cif
_cod_data_source_block           mb-mn-688-s
_cod_depositor_comments          'Adding full bibliography for 7156800.cif.'
_cod_database_code               7156800
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C13 H14 N2'
_chemical_oxdiff_usercomment     'COLOURLESSBLOCK, 298K, 0.36 0.34 0.24'
_reflns_odcompleteness_completeness 99.48
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29),
 C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
  C40(H40), C42(H42), C44(H44), C46(H46), C47(H47), C48(H48), C49(H49),
 C50(H50), C52(H52), C53(H53), C54(H54)
2.b Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C51(H51A,H51B,H51C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              88942
_olex2_submission_special_instructions 'No special instructions were received'