One-Pot Synthesis of Diverse Collections of Benzoxazepine and Indolopyrazine Fused to Heterocyclic Systems.
Srinivasulu, Vunnam; Shehadeh, Ihsan; Khanfar, Monther A.; Malik, Omar G.; Tarazi, Hamadeh; Abu-Yousef, Imad A; Sebastian, Anusha; Baniowda, Nabil; O'Connor, Matthew John; Al-Tel, Taleb H; The Journal of organic chemistry 84 (2019) 934–948; doi:10.1021/acs.joc.8b02878

data_4035968
_publ_section_title
;
 One-Pot Synthesis of Diverse Collections of Benzoxazepine and
 Indolopyrazine Fused to Heterocyclic Systems.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              934
_journal_page_last               948
_journal_paper_doi               10.1021/acs.joc.8b02878
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_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     dual
_audit_creation_date             2018-10-25
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.01.05 svn.r3372 for Rigaku Oxford Diffraction, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.04(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.674(3)
_cell_length_b                   7.0239(14)
_cell_length_c                   18.455(4)
_cell_measurement_reflns_used    2181
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.3200
_cell_measurement_theta_min      3.3960
_cell_volume                     1562.1(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0267
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.895
_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    -25.00  23.00   1.00   50.00    --  -16.36 -99.00 -30.00   48
  2  \w     23.00  71.00   1.00   50.00    --   16.98  57.00 120.00   48
  3  \w      8.00  81.00   1.00   50.00    --   16.98  57.00  60.00   73
  4  \w    -44.00  31.00   1.00   50.00    --   16.98 -57.00 120.00   75
  5  \w    -66.00 -41.00   1.00   50.00    --  -16.04 118.00-127.80   25
  6  \w    -72.00 -28.00   1.00   50.00    --  -16.04 129.00 156.53   44
  7  \w    -81.00 -47.00   1.00   50.00    --  -16.04 -77.00-180.00   34
  8  \w    -27.00   8.00   1.00   50.00    --  -16.04 118.00-127.80   35
  9  \w     35.00  73.00   1.00   50.00    --   16.83 178.00 120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0561842000
_diffrn_orient_matrix_UB_12      0.0013080000
_diffrn_orient_matrix_UB_13      -0.0005242000
_diffrn_orient_matrix_UB_21      -0.0174122000
_diffrn_orient_matrix_UB_22      0.0050448000
_diffrn_orient_matrix_UB_23      -0.0403538000
_diffrn_orient_matrix_UB_31      -0.0016237000
_diffrn_orient_matrix_UB_32      -0.1009285000
_diffrn_orient_matrix_UB_33      -0.0020411000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0781
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13215
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.264
_diffrn_reflns_theta_min         3.124
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       0.13(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.576
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.576
_refine_ls_R_factor_all          0.2238
_refine_ls_R_factor_gt           0.1689
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4550
_refine_ls_wR_factor_ref         0.4844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2102
_reflns_number_total             3816
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02878_si_004.cif
_cod_data_source_block           exp_2463
_cod_database_code               4035968
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 H16 N2 O4'
_chemical_oxdiff_usercomment     'Raed 2162-repeat'
_reflns_odcompleteness_completeness 91.83
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00D(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O)
2.d Idealised Me refined as rotating group:
 C00P(H00E,H00F,H00G)
;
_olex2_date_sample_data_collection 2018-10-24
_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 1.246
_oxdiff_exptl_absorpt_empirical_full_min 0.754