Direct synthesis of ring-fused quinolines and pyridines catalyzed by NNHY-ligated manganese complexes (Y = NR2 or SR)
Wang, Zheng; Lin, Qing; Ma, Ning; Liu, Song; Han, Mingyang; Yan, Xiuli; Liu, Qingbin; Solan, Gregory A.; Sun, Wen-Hua; Catalysis Science & Technology 11 (2021) 8026–8036; doi:10.1039/D1CY01945G

data_1565138
_publ_section_title
;
 Direct synthesis of ring-fused quinolines and pyridines catalyzed by
 NNHY-ligated manganese complexes (Y = NR2 or SR)
;
_journal_issue                   24
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              8026
_journal_page_last               8036
_journal_paper_doi               10.1039/D1CY01945G
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'Br, C16 H21 Mn N3 O3, H2 O'
_chemical_formula_sum            'C16 H23 Br Mn N3 O4'
_chemical_formula_weight         456.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2021-03-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2021-05-22 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                87.2665(19)
_cell_angle_beta                 76.201(2)
_cell_angle_gamma                70.5516(19)
_cell_formula_units_Z            2
_cell_length_a                   7.94037(15)
_cell_length_b                   10.1189(2)
_cell_length_c                   12.8889(3)
_cell_measurement_reflns_used    9156
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      74.6300
_cell_measurement_theta_min      3.5280
_cell_volume                     947.75(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9616
_diffrn_measured_fraction_theta_max 0.9616
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1743895000
_diffrn_orient_matrix_UB_12      0.0416001000
_diffrn_orient_matrix_UB_13      -0.0182402000
_diffrn_orient_matrix_UB_21      0.1170352000
_diffrn_orient_matrix_UB_22      -0.1463009000
_diffrn_orient_matrix_UB_23      -0.0510573000
_diffrn_orient_matrix_UB_31      -0.0270600000
_diffrn_orient_matrix_UB_32      0.0544579000
_diffrn_orient_matrix_UB_33      -0.1105752000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10618
_diffrn_reflns_theta_full        75.1626
_diffrn_reflns_theta_max         75.16
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5985
_exptl_crystal_description       block
_exptl_crystal_F_000             462.7874
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.6310
_refine_diff_density_min         -0.5582
_refine_diff_density_rms         0.0833
_refine_ls_d_res_high            0.7975
_refine_ls_d_res_low             12.5094
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0285
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0285
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.5098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0894
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3690
_reflns_number_total             3755
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cy01945g2.cif
_cod_data_source_block           Mn1
_cod_depositor_comments
'Adding full bibliography for 1565138--1565140.cif.'
_cod_original_cell_volume        947.76(4)
_cod_database_code               1565138
_chemical_oxdiff_usercomment     'Mo N C H O'
_diffrn_oxdiff_ac3_digest_frames
;
0179ed09b7a517c07a5d1c597003aea1ff0332612c4
;
_diffrn_oxdiff_ac3_digest_hkl
;
0143abf0803241c2a0393694d6fbe61a45f71c
;
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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,H) groups
2.a Free rotating group:
 O4(H4a,H4b)
2.b Ternary CH refined with riding coordinates:
 N2(H2), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C10(H10a,H10b), C6(H6a,H6b), C11(H11a,H11b), C5(H5a,H5b)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2a)
2.e Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.409
_oxdiff_exptl_absorpt_empirical_full_min 0.708