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_4035970
_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         'C24 H22 N2 O3'
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.34(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.306(3)
_cell_length_b                   9.758(2)
_cell_length_c                   17.335(5)
_cell_measurement_reflns_used    741
_cell_measurement_temperature    291
_cell_measurement_theta_max      21.4310
_cell_measurement_theta_min      3.7630
_cell_volume                     2007.5(9)
_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      291
_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 0.872
_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      5.00  84.00   1.00   50.00    --   17.14  57.00  30.00   79
  2  \w      3.00  39.00   1.00   50.00    --   17.14  57.00 -90.00   36
  3  \w      0.00  84.00   1.00   50.00    --   17.14  57.00-180.00   84
  4  \w    -15.00  19.00   1.00   50.00    --  -16.36 -99.00   0.00   34
  5  \w    -43.00  34.00   1.00   50.00    --   17.14 -57.00 -90.00   77
  6  \w    -46.00  43.00   1.00   50.00    --   17.14 -75.00  58.00   89
;
_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      0.0102751000
_diffrn_orient_matrix_UB_12      -0.0627777000
_diffrn_orient_matrix_UB_13      0.0215328000
_diffrn_orient_matrix_UB_21      0.0189635000
_diffrn_orient_matrix_UB_22      0.0366771000
_diffrn_orient_matrix_UB_23      0.0362660000
_diffrn_orient_matrix_UB_31      -0.0557365500
_diffrn_orient_matrix_UB_32      0.0008484500
_diffrn_orient_matrix_UB_33      0.0042178500
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1079
_diffrn_reflns_av_unetI/netI     0.2602
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7497
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.565
_diffrn_reflns_theta_min         3.321
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81036
_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    1.279
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(10)
_refine_ls_extinction_coef       0.0020(12)
_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   0.874
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.874
_refine_ls_R_factor_all          0.2353
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0730P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.2567
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.850
_reflns_Friedel_fraction_max     0.648
_reflns_number_gt                1218
_reflns_number_total             4280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02878_si_003.cif
_cod_data_source_block           exp_2413
_cod_original_cell_volume        2007.5(8)
_cod_database_code               4035970
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C22 H22 N2 O3'
_chemical_oxdiff_usercomment     Raed-2139
_reflns_odcompleteness_completeness 99.77
_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:
 C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00B), C00L(H00C,H00D)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00P(H00P),
 C00Q(H00Q), C00R(H00R)
2.d Idealised Me refined as rotating group:
 C00O(H00E,H00F,H00G), C00S(H00I,H00L,H00O), C00T(H00S,H00T,H00U)
;
_olex2_date_sample_data_collection 2018-09-12
_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 3.426
_oxdiff_exptl_absorpt_empirical_full_min 0.697