Site-Selective Reaction of Enaminones and Enamine Esters for the Synthesis of Novel Diverse Morphan Derivatives.
Hu, Xing-Mei; Zhou, Bei; Yang, Chang-Long; Lin, Jun; Yan, Sheng-Jiao; ACS omega 3 (2018) 5994–6005; doi:10.1021/acsomega.8b00726

data_4516057
_publ_section_title
;
 Site-Selective Reaction of Enaminones and Enamine Esters for the
 Synthesis of Novel Diverse Morphan Derivatives.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              5994
_journal_page_last               6005
_journal_paper_doi               10.1021/acsomega.8b00726
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C16 H22 F3 N O5'
_chemical_formula_sum            'C16 H22 F3 N O5'
_chemical_formula_weight         365.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-28
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.158(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7813(11)
_cell_length_b                   8.4703(11)
_cell_length_c                   24.136(3)
_cell_measurement_reflns_used    2273
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      22.085
_cell_measurement_theta_min      2.796
_cell_volume                     1792.5(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      297.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10502
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.596
_diffrn_reflns_theta_min         2.549
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0431 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.9406. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4068
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0587
_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^)+(0.0754P)^2^+0.5684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1776
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             4068
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao8b00726_si_003.cif
_cod_data_source_block           hxmxat18_0m
_cod_database_code               4516057
_shelx_shelxl_version_number     2016/6
_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 Ternary CH refined with riding coordinates:
 C3(H3), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C12(H12A,H12B), C14(H14A,H14B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              61889
_shelx_hkl_checksum              50934
_olex2_submission_special_instructions 'No special instructions were received'