Controllable synthesis of 2- and 3-aryl-benzomorpholines from 2-aminophenols and 4-vinylphenols.
Dong, Kui; Jin, Xiao-Ling; Chen, Shihao; Wu, Li-Zhu; Liu, Qiang; Chemical communications (Cambridge, England) 56 (2020) 7941–7944; doi:10.1039/d0cc02662j

data_7126646
_publ_section_title
;
 Controllable synthesis of 2- and 3-aryl-benzomorpholines from
 2-aminophenols and 4-vinylphenols.
;
_journal_issue                   57
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7941
_journal_page_last               7944
_journal_paper_doi               10.1039/d0cc02662j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C16 H16 Cl N O3'
_chemical_formula_sum            'C16 H16 Cl N O3'
_chemical_formula_weight         305.74
_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     direct
_audit_creation_date             2018-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                93.513(9)
_cell_angle_beta                 110.671(9)
_cell_angle_gamma                113.518(10)
_cell_formula_units_Z            4
_cell_length_a                   10.6908(9)
_cell_length_b                   11.1997(13)
_cell_length_c                   14.8988(16)
_cell_measurement_reflns_used    1555
_cell_measurement_temperature    294.97(10)
_cell_measurement_theta_max      24.9970
_cell_measurement_theta_min      4.0020
_cell_volume                     1487.3(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.97(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -13.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836  -99.0000 -180.0000 37

  2 omega    3.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5836   57.0000 -150.0000 48

  3 omega   -2.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430   77.0000  -60.0000 27

  4 omega  -48.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -57.0000  -60.0000 95

  5 omega   -1.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430   57.0000   90.0000 94

  6 omega  -18.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -99.0000 -180.0000 66
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0366258000
_diffrn_orient_matrix_UB_12      -0.0352460000
_diffrn_orient_matrix_UB_13      0.0270622000
_diffrn_orient_matrix_UB_21      0.0542678000
_diffrn_orient_matrix_UB_22      0.0604843000
_diffrn_orient_matrix_UB_23      0.0357474000
_diffrn_orient_matrix_UB_31      -0.0449696000
_diffrn_orient_matrix_UB_32      -0.0122615000
_diffrn_orient_matrix_UB_33      0.0270394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9095
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.385
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.1579P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1678
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3441
_reflns_number_total             5855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc02662j2.cif
_cod_data_source_block           dongk_1029
_cod_depositor_comments
;
Adding full bibliography for 7126646--7126647.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C16 H16 Cl N O3)'
_cod_original_formula_sum        'C32 H32 Cl2 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     611.49
_cod_database_code               7126646
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.72
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 N6(H6), N17(H17)
2.b Ternary CH refined with riding coordinates:
 C9(H9), C27(H27), C33(H33), C36(H36)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C14(H14), C18(H18), C20(H20), C21(H21), C29(H29),
 C31(H31), C34(H34), C35(H35), C38(H38)
2.d Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C40(H40a,H40b,H40c), C41(H41a,H41b,H41c), C0AA(H0Aa,H0Ab,
 H0Ac)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O28(H28)
;
_shelx_res_checksum              8120
_olex2_date_sample_data_collection 2018-10-29
_olex2_submission_special_instructions 'No special instructions were received'