#------------------------------------------------------------------------------
#$Date: 2022-01-06 22:40:52 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271826 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/51/1565139.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1565139
loop_
_publ_author_name
'Wang, Zheng'
'Lin, Qing'
'Ma, Ning'
'Liu, Song'
'Han, Mingyang'
'Yan, Xiuli'
'Liu, Qingbin'
'Solan, Gregory A.'
'Sun, Wen-Hua'
_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 & 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 H20 Mn N2 O3 S'
_chemical_formula_sum            'C16 H20 Br Mn N2 O3 S'
_chemical_formula_weight         455.26
_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
_audit_creation_date             2021-03-29
_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                103.0666(16)
_cell_angle_beta                 101.3527(15)
_cell_angle_gamma                108.6668(17)
_cell_formula_units_Z            2
_cell_length_a                   7.71788(15)
_cell_length_b                   10.1753(2)
_cell_length_c                   13.2154(2)
_cell_measurement_reflns_used    8904
_cell_measurement_temperature    169.98(10)
_cell_measurement_theta_max      75.1460
_cell_measurement_theta_min      4.8070
_cell_volume                     916.12(3)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1843806000
_diffrn_orient_matrix_UB_12      0.1212110000
_diffrn_orient_matrix_UB_13      0.0034844000
_diffrn_orient_matrix_UB_21      -0.0504917000
_diffrn_orient_matrix_UB_22      0.1144193000
_diffrn_orient_matrix_UB_23      0.0732295000
_diffrn_orient_matrix_UB_31      0.1094289000
_diffrn_orient_matrix_UB_32      -0.0222255000
_diffrn_orient_matrix_UB_33      0.1013834000
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0209
_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       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10617
_diffrn_reflns_theta_full        75.2343
_diffrn_reflns_theta_max         75.23
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35222
_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    1.6503
_exptl_crystal_description       block
_exptl_crystal_F_000             459.3214
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.7445
_refine_diff_density_min         -0.6728
_refine_diff_density_rms         0.0944
_refine_ls_d_res_high            0.7972
_refine_ls_d_res_low             9.1613
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0414
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0414
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0651P)²+0.5318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0919
_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                3546
_reflns_number_total             3608
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d1cy01945g2.cif
_cod_data_source_block           Mn4
_cod_depositor_comments
'Adding full bibliography for 1565138--1565140.cif.'
_cod_database_code               1565139
_chemical_oxdiff_formula         'C H N S Mn Br'
_diffrn_oxdiff_ac3_digest_frames
;
01c1fe2e3d79799f83b88ed21405287bde034326357
;
_diffrn_oxdiff_ac3_digest_hkl
;
0120afe98c17d910e670e0fa1a88a61dbc43ca
;
_reflns_odcompleteness_completeness 99.91
_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
2.a Ternary CH refined with riding coordinates:
 N2(H2), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C10(H10a,H10b), C7(H7a,H7b), C11(H11a,H11b), C5(H5a,H5b),
 C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C1(H1), C2(H2a)
2.d Idealised Me refined as rotating group:
 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 1.671
_oxdiff_exptl_absorpt_empirical_full_min 0.735
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br1 Br 0.29636(3) 0.66089(3) 0.847498(19) 0.02781(12) Uani 1.000000 .
Mn1 Mn 0.36020(5) 0.24333(4) 0.71784(3) 0.01781(12) Uani 1.000000 .
S1 S 0.61519(8) 0.17071(6) 0.77589(4) 0.02217(15) Uani 1.000000 .
O1 O 0.0322(3) 0.3211(2) 0.63678(15) 0.0332(4) Uani 1.000000 .
N2 N 0.5482(3) 0.4522(2) 0.81536(14) 0.0183(4) Uani 1.000000 .
H2 H 0.4774(3) 0.4940(2) 0.84848(14) 0.0220(4) Uiso 1.000000 R
N1 N 0.5058(3) 0.3044(2) 0.61029(15) 0.0199(4) Uani 1.000000 .
O2 O 0.1858(3) 0.1899(3) 0.89192(17) 0.0419(5) Uani 1.000000 .
O3 O 0.1198(3) -0.0562(2) 0.57524(18) 0.0464(5) Uani 1.000000 .
C9 C 0.6266(3) 0.4455(2) 0.64304(17) 0.0181(4) Uani 1.000000 .
C12 C 0.5710(4) 0.0772(3) 0.8764(2) 0.0248(5) Uani 1.000000 .
H12a H 0.5474(4) 0.1393(3) 0.9350(2) 0.0298(6) Uiso 1.000000 R
H12b H 0.4572(4) -0.0115(3) 0.8429(2) 0.0298(6) Uiso 1.000000 R
C4 C 0.7426(3) 0.5027(3) 0.58221(19) 0.0218(5) Uani 1.000000 .
C10 C 0.6963(3) 0.4476(3) 0.90369(18) 0.0233(5) Uani 1.000000 .
H10a H 0.7910(3) 0.5455(3) 0.94138(18) 0.0280(6) Uiso 1.000000 R
H10b H 0.6374(3) 0.4118(3) 0.95564(18) 0.0280(6) Uiso 1.000000 R
C8 C 0.6182(3) 0.5410(2) 0.74539(17) 0.0176(4) Uani 1.000000 .
H8 H 0.5195(3) 0.5781(2) 0.72248(17) 0.0212(5) Uiso 1.000000 R
C3 C 0.7259(3) 0.4102(3) 0.48328(19) 0.0251(5) Uani 1.000000 .
H3 H 0.7977(3) 0.4457(3) 0.43952(19) 0.0302(6) Uiso 1.000000 R
C7 C 0.8031(3) 0.6753(2) 0.80164(19) 0.0215(4) Uani 1.000000 .
H7a H 0.7870(3) 0.7395(2) 0.86237(19) 0.0258(5) Uiso 1.000000 R
H7b H 0.9060(3) 0.6459(2) 0.82928(19) 0.0258(5) Uiso 1.000000 R
C1 C 0.4975(3) 0.2158(3) 0.51529(19) 0.0250(5) Uani 1.000000 .
H1 H 0.4176(3) 0.1178(3) 0.49359(19) 0.0300(6) Uiso 1.000000 R
C14 C 0.1650(3) 0.2992(3) 0.66810(18) 0.0235(5) Uani 1.000000 .
C15 C 0.2558(3) 0.2092(3) 0.8251(2) 0.0256(5) Uani 1.000000 .
C11 C 0.7930(3) 0.3501(3) 0.8592(2) 0.0272(5) Uani 1.000000 .
H11a H 0.8789(3) 0.3403(3) 0.9187(2) 0.0327(6) Uiso 1.000000 R
H11b H 0.8680(3) 0.3935(3) 0.8158(2) 0.0327(6) Uiso 1.000000 R
C5 C 0.8858(4) 0.6583(3) 0.6258(2) 0.0306(5) Uani 1.000000 .
H5a H 1.0126(4) 0.6575(3) 0.6495(2) 0.0367(7) Uiso 1.000000 R
H5b H 0.8832(4) 0.7009(3) 0.5671(2) 0.0367(7) Uiso 1.000000 R
C6 C 0.8525(4) 0.7553(3) 0.7198(2) 0.0276(5) Uani 1.000000 .
H6a H 0.7487(4) 0.7838(3) 0.6921(2) 0.0332(6) Uiso 1.000000 R
H6b H 0.9667(4) 0.8432(3) 0.7557(2) 0.0332(6) Uiso 1.000000 R
C16 C 0.2142(4) 0.0608(3) 0.6308(2) 0.0277(5) Uani 1.000000 .
C13 C 0.7372(4) 0.0387(3) 0.9229(2) 0.0330(6) Uani 1.000000 .
H13a H 0.770(2) -0.014(2) 0.8646(2) 0.0494(8) Uiso 1.000000 GR
H13b H 0.8453(10) 0.1265(3) 0.9653(15) 0.0494(8) Uiso 1.000000 GR
H13c H 0.7015(11) -0.021(2) 0.9682(14) 0.0494(8) Uiso 1.000000 GR
C2 C 0.6032(4) 0.2652(3) 0.44891(19) 0.0280(5) Uani 1.000000 .
H2a H 0.5922(4) 0.2024(3) 0.38265(19) 0.0337(6) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Mn -0.54371 2.83629 11.28190 7.35730 3.01930 2.24410 5.34090 0.34320 17.86740
83.75430 1.089599967 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Mn1 S1 85.28(5) . . ?
N1 Mn1 S1 83.26(5) . . ?
N1 Mn1 N2 80.76(7) . . ?
C14 Mn1 S1 177.86(7) . . ?
C14 Mn1 N2 95.17(9) . . ?
C14 Mn1 N1 94.73(9) . . ?
C15 Mn1 S1 94.61(8) . . ?
C15 Mn1 N2 92.31(9) . . ?
C15 Mn1 N1 172.87(9) . . ?
C15 Mn1 C14 87.47(10) . . ?
C16 Mn1 S1 91.07(8) . . ?
C16 Mn1 N2 175.38(10) . . ?
C16 Mn1 N1 96.03(10) . . ?
C16 Mn1 C14 88.38(11) . . ?
C16 Mn1 C15 90.80(11) . . ?
C12 S1 Mn1 110.25(8) . . ?
C11 S1 Mn1 98.06(8) . . ?
C11 S1 C12 102.55(12) . . ?
C10 N2 Mn1 111.57(13) . . ?
C8 N2 Mn1 109.43(13) . . ?
C8 N2 C10 116.55(17) . . ?
C9 N1 Mn1 115.29(14) . . ?
C1 N1 Mn1 126.09(16) . . ?
C1 N1 C9 118.5(2) . . ?
C4 C9 N1 122.5(2) . . ?
C8 C9 N1 115.81(18) . . ?
C8 C9 C4 121.5(2) . . ?
C13 C12 S1 112.44(17) . . ?
C3 C4 C9 117.6(2) . . ?
C5 C4 C9 120.7(2) . . ?
C5 C4 C3 121.7(2) . . ?
C11 C10 N2 111.04(19) . . ?
C9 C8 N2 110.56(17) . . ?
C7 C8 N2 115.59(18) . . ?
C7 C8 C9 112.39(18) . . ?
C2 C3 C4 120.5(2) . . ?
C6 C7 C8 108.97(19) . . ?
C2 C1 N1 122.4(2) . . ?
O1 C14 Mn1 173.4(2) . . ?
O2 C15 Mn1 177.7(2) . . ?
C10 C11 S1 110.20(16) . . ?
C6 C5 C4 114.7(2) . . ?
C5 C6 C7 110.8(2) . . ?
O3 C16 Mn1 179.6(3) . . ?
C1 C2 C3 118.4(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 S1 2.3665(6) . ?
Mn1 N2 2.0821(18) . ?
Mn1 N1 2.0620(19) . ?
Mn1 C14 1.831(3) . ?
Mn1 C15 1.809(2) . ?
Mn1 C16 1.796(3) . ?
S1 C12 1.825(2) . ?
S1 C11 1.822(2) . ?
O1 C14 1.137(3) . ?
N2 C10 1.485(3) . ?
N2 C8 1.491(3) . ?
N1 C9 1.349(3) . ?
N1 C1 1.346(3) . ?
O2 C15 1.144(3) . ?
O3 C16 1.152(3) . ?
C9 C4 1.395(3) . ?
C9 C8 1.503(3) . ?
C12 C13 1.515(3) . ?
C4 C3 1.383(3) . ?
C4 C5 1.509(3) . ?
C10 C11 1.507(4) . ?
C8 C7 1.527(3) . ?
C3 C2 1.383(4) . ?
C7 C6 1.530(3) . ?
C1 C2 1.381(4) . ?
C5 C6 1.523(4) . ?
