Structure-Based Kinetic Control in a Domino Process: A Powerful Tool Toward Molecular Diversity in Chromone Series.
Lepitre, Thomas; Denhez, Clement; Moncol, Jan; Othman, Mohamed; Lawson, Ata Martin; Daïch, Adam; The Journal of organic chemistry 82 (2017) 12188–12201; doi:10.1021/acs.joc.7b01996

data_4033029
_publ_section_title
;
 Structure-Based Kinetic Control in a Domino Process: A Powerful Tool
 Toward Molecular Diversity in Chromone Series.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12188
_journal_page_last               12201
_journal_paper_doi               10.1021/acs.joc.7b01996
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H19 N O5'
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.863(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0386(3)
_cell_length_b                   24.2827(13)
_cell_length_c                   12.1901(6)
_cell_measurement_reflns_used    21386
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.80
_cell_measurement_theta_min      3.64
_cell_volume                     1486.10(14)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus300K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21185
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.289
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.663
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   X-AREA
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2801
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0456
_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^)+(0.0640P)^2^+0.9563P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2360
_reflns_number_total             2801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01996_si_002.cif
_cod_data_source_block           05tlp113
_cod_depositor_comments          'Adding full bibliography for 4033029.cif.'
_cod_database_code               4033029
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.687
_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, All O(H) groups
2. Restrained distances
 O4-C15 \\sim O4-C15A
 with sigma of 0.02
 C14-C15 \\sim C14-C15A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) = Uanis(C15A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C1(H1A)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B), C15A(H15C,H15D)
6.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
6.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'