Selective remote esterification of 8-aminoquinoline amides via copper(ii)-catalyzed C(sp(2))-O cross-coupling reaction.
Xia, Chengcai; Wang, Kai; Xu, Jun; Shen, Chao; Sun, Di; Li, Hongshuang; Wang, Guodong; Zhang, Pengfei; Organic & biomolecular chemistry 15 (2017) 531–535; doi:10.1039/c6ob02375d

data_7155394
_publ_section_title
;
 Selective remote esterification of 8-aminoquinoline amides via
 copper(ii)-catalyzed C(sp(2))-O cross-coupling reaction.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              531
_journal_page_last               535
_journal_paper_doi               10.1039/c6ob02375d
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 N2 O3'
_chemical_formula_sum            'C19 H16 N2 O3'
_chemical_formula_weight         320.34
_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'
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-10-04 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.055(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1225(6)
_cell_length_b                   16.4269(15)
_cell_length_c                   15.5669(14)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.137
_cell_measurement_theta_min      3.333
_cell_volume                     1563.4(3)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26832
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0651 before and 0.0576 after correction.
The Ratio of minimum to maximum transmission is 0.9301.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0779P)^2^+0.3510P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                2065
_reflns_number_total             2751
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02375d2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7155394.cif.'
_cod_database_code               7155394
_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
2.a Riding coordinates:
 C19(H19A,H19B,H19C)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C10(H10), C4(H4), C11(H11), C6(H6), C16(H16), C14(H14), C3(H3),
 C5(H5), C15(H15)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'