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_4035966
_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         'C27 H27 N3 O6 S'
_chemical_formula_sum            'C27 H27 N3 O6 S'
_chemical_formula_weight         521.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.359(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.795(4)
_cell_length_b                   6.7049(8)
_cell_length_c                   43.048(8)
_cell_measurement_reflns_used    1135
_cell_measurement_temperature    293
_cell_measurement_theta_max      20.1860
_cell_measurement_theta_min      3.7280
_cell_volume                     5318.6(17)
_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 0.999
_diffrn_measured_fraction_theta_max 0.861
_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    -85.00 -13.00   0.75   60.00    --  -16.20 -38.00-120.00   96
  2  \w    -25.00  52.25   0.75   60.00    --  -16.20  38.00-120.00  103
  3  \w    -30.00  34.50   0.75   60.00    --  -16.20  57.00   0.00   86
  4  \w    -21.00  18.00   0.75   60.00    --  -16.20 -99.00-120.00   52
;
_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      -0.0306831500
_diffrn_orient_matrix_UB_12      0.0037049500
_diffrn_orient_matrix_UB_13      0.0072941500
_diffrn_orient_matrix_UB_21      0.0231980500
_diffrn_orient_matrix_UB_22      -0.0043691500
_diffrn_orient_matrix_UB_23      0.0151332500
_diffrn_orient_matrix_UB_31      0.0020504500
_diffrn_orient_matrix_UB_32      0.1055989500
_diffrn_orient_matrix_UB_33      0.0003474500
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_av_unetI/netI     0.2110
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            14185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.160
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71149
_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    1.303
_exptl_crystal_description       needle
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         6180
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.2989
_refine_ls_R_factor_gt           0.1039
_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^)+(0.0450P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1992
_reflns_number_total             6180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02878_si_005.cif
_cod_data_source_block           exp_2461
_cod_original_cell_volume        5318.7(16)
_cod_database_code               4035966
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C27 H27 N3 O6 S1'
_chemical_oxdiff_usercomment     'Raed 2195-repeat'
_reflns_odcompleteness_completeness 91.62
_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 Riding coordinates:
 N005(H005)
2.b Ternary CH refined with riding coordinates:
 C00C(H00C), C00K(H00K)
2.c Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00B), C00N(H00D,H00E)
2.d Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00J(H00J), C00O(H00O), C00R(H00R), C00S(H00S),
 C00U(H00U), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C011(H011)
2.e Idealised Me refined as rotating group:
 C00Q(H00F,H00I,H00L), C00V(H00M,H00N,H00P), C010(H01A,H01B,H01C)
;
_olex2_date_sample_data_collection 2018-10-23
_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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.802