Aminations and arylations by direct C‒O activation for the design of 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines
Laurent, Mazarine; Bostyn, Stéphane; Marchivie, Mathieu; Robin, Yves; Routier, Sylvain; Buron, Frédéric; RSC Advances 11 (2021) 19363–19377; doi:10.1039/D1RA03092B

data_7242946
_publ_section_title
;
 Aminations and arylations by direct C--O activation for the design of
 7,8-dihydro-6H-5,8-ethanopyrido[3,2-d]pyrimidines
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              19363
_journal_page_last               19377
_journal_paper_doi               10.1039/D1RA03092B
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 F3 N3'
_chemical_formula_sum            'C22 H18 F3 N3'
_chemical_formula_weight         381.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-01 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.051(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3849(12)
_cell_length_b                   5.8934(4)
_cell_length_c                   22.187(2)
_cell_measurement_reflns_used    7784
_cell_measurement_temperature    299.59
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.77
_cell_volume                     1889.7(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      299.59
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.927
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.927
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16348
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.409
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1312 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8031.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6319
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0820P)^2^+0.3594P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.926
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                4557
_reflns_number_total             6319
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra03092b2.cif
_cod_data_source_block           mzl_e_501_0m
_cod_original_cell_volume        1889.8(3)
_cod_database_code               7242946
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(F3AA)=1-FVAR(1)
 Sof(F3BA)=FVAR(1)
 Sof(F3BB)=1-FVAR(2)
 Sof(F3AB)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C3A(H3A), C3B(H3B)
3.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C1B(H1BA,
 H1BB), C2B(H2BA,H2BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB)
3.c Aromatic/amide H refined with riding coordinates:
 C11A(H11A), C12A(H12A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C20A(H20A), C21A(H21A), C22A(H22A), C11B(H11B), C12B(H12B), C14B(H14B),
 C15B(H15B), C18B(H18B), C19B(H19B), C20B(H20B), C21B(H21B), C22B(H22B)
;
_shelx_res_checksum              25973
_olex2_submission_special_instructions 'No special instructions were received'