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_4035967
_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         'C18 H14 Cl2 N2 O3'
_chemical_formula_sum            'C18 H14 Cl2 N2 O3'
_chemical_formula_weight         377.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_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                96.348(9)
_cell_angle_beta                 99.163(11)
_cell_angle_gamma                108.189(12)
_cell_formula_units_Z            4
_cell_length_a                   7.1605(12)
_cell_length_b                   11.4577(14)
_cell_length_c                   22.362(2)
_cell_measurement_reflns_used    2648
_cell_measurement_temperature    291
_cell_measurement_theta_max      24.3000
_cell_measurement_theta_min      3.7360
_cell_volume                     1695.4(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.887
_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    -32.00  47.00   1.00   90.00    --  -16.04  38.00 150.00   79
  2  \w     -9.00  17.00   1.00   90.00    --  -16.04 -99.00 120.00   26
  3  \w     27.00  63.00   1.00   90.00    --   16.83  57.00   0.00   36
  4  \w     -7.00  75.00   1.00   90.00    --   16.83  77.00 -90.00   82
  5  \w    -59.00 -30.00   1.00   22.50    --  -16.04 106.00 100.15   29
  6  \w    -63.00  13.00   1.00   22.50    --  -16.04 113.00-177.38   76
  7  \w    -67.00   6.00   1.00   22.50    --  -16.04 120.00 -42.19   73
  8  \w    -83.00  -4.00   1.00   22.50    --  -16.04 -57.00 150.00   79
  9  \w      3.00  29.00   1.00   22.50    --   16.83  38.00  30.00   26
 10  \w     40.00  81.00   1.00   22.50    --   16.83  38.00  30.00   41
 11  \w    -45.00  31.00   1.00   22.50    --   16.83 -77.00 -60.00   76
 12  \w    -42.00  27.00   1.00   22.50    --   16.83 -57.00  30.00   69
 13  \w      7.00  82.00   1.00   22.50    --   16.83  57.00  90.00   75
;
_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      -0.0338310000
_diffrn_orient_matrix_UB_12      0.0432588000
_diffrn_orient_matrix_UB_13      -0.0150250000
_diffrn_orient_matrix_UB_21      -0.0905193000
_diffrn_orient_matrix_UB_22      -0.0195082000
_diffrn_orient_matrix_UB_23      0.0110003000
_diffrn_orient_matrix_UB_31      0.0448393000
_diffrn_orient_matrix_UB_32      0.0460625000
_diffrn_orient_matrix_UB_33      0.0267652000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1123
_diffrn_reflns_av_unetI/netI     0.1637
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.311
_diffrn_reflns_theta_min         2.886
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69385
_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    1.478
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         8214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.2402
_refine_ls_R_factor_gt           0.0810
_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^)+(0.1080P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2017
_refine_ls_wR_factor_ref         0.2760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2793
_reflns_number_total             8214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02878_si_002.cif
_cod_data_source_block           exp_2411
_cod_original_cell_volume        1695.5(4)
_cod_database_code               4035967
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C18 H14 Cl2 N2 O3'
_chemical_oxdiff_usercomment     Raed-2137
_reflns_odcompleteness_completeness 99.90
_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:
 C00Y(H00Y), C00Z(H00Z)
2.b Secondary CH2 refined with riding coordinates:
 C018(H01H,H01I), C01A(H01A,H01B), C01C(H01J,H01K)
2.c Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00N(H00N), C00O(H00O), C00T(H00T), C00U(H00U), C00W(H00W),
 C010(H010), C011(H011), C013(H013), C014(H014), C016(H016), C017(H017)
2.d Idealised Me refined as rotating group:
 C01D(H01E,H01F,H01G), C01E(H01L,H01M,H01N)
;
_olex2_date_sample_data_collection 2018-09-10
_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 1.300
_oxdiff_exptl_absorpt_empirical_full_min 0.814