# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ar14-29
_database_code_depnum_ccdc_archive 'CCDC 2362473'
loop_
_audit_author_name
_audit_author_address
'Hai-Xia Zhang'
;FJIRSM
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 B Cu N6 O2 S'
_chemical_formula_sum            'C17 H19 B Cu N6 O2 S'
_chemical_formula_weight         445.81
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O B Cu S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.8870 3.6900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   17.1231(3)
_cell_length_b                   8.8768(2)
_cell_length_c                   13.2163(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.837(2)
_cell_angle_gamma                90
_cell_volume                     2006.39(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7695
_cell_measurement_temperature    298.69(10)
_cell_measurement_theta_max      60.1510
_cell_measurement_theta_min      3.6010
_shelx_estimated_absorpt_T_max   0.350
_shelx_estimated_absorpt_T_min   0.205
_exptl_absorpt_coefficient_mu    6.633
_exptl_absorpt_correction_T_max  0.265
_exptl_absorpt_correction_T_min  0.254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9342
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        51.202
_diffrn_reflns_theta_max         51.202
_diffrn_reflns_theta_min         4.496
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.69(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  24.00   0.50    0.08    --   -1.56 -81.00 -51.00  196
  2  ω    -27.00  71.00   0.50    0.08    --   -1.56  81.00  70.00  196
  3  ω      0.00  98.00   0.50    0.32    --   72.34 -81.00 -51.00  196
  4  ω     47.00 145.00   0.50    0.32    --   72.34  81.00  70.00  196
  5  ω   -101.00  -2.00   0.50    0.32    --  -75.46  81.00  70.00  198
  6  ω    -16.00  72.00   0.50    0.08    --   -1.56  38.00-180.00  176
  7  ω     -3.00  27.00   0.50    0.32    --   72.34 -19.00   0.00   60
  8  ω     -3.00  27.00   0.50    0.32    --   72.34 -19.00  90.00   60
  9  ω     -1.00  43.00   0.50    0.32    --   72.34 -38.00 -30.00   88
 10  ω     -1.00  43.00   0.50    0.32    --   72.34 -38.00   0.00   88
 11  ω     -1.00  43.00   0.50    0.32    --   72.34 -38.00 120.00   88
 12  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00 -90.00   54
 13  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00  90.00   54
 14  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00-120.00   54
 15  ω    -43.00  -2.00   0.50    0.32    --  -75.46  38.00   0.00   82
 16  ω    -43.00  -2.00   0.50    0.32    --  -75.46  38.00-150.00   82
 17  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00-150.00   54
 18  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00 -60.00   54
 19  ω    -27.00   0.00   0.50    0.32    --  -75.46  19.00  30.00   54
 20  ω   -148.00 -50.00   0.50    0.32    --  -75.46 -81.00 -51.00  196
 21  ω    -16.00  30.00   0.50    0.08    --   -1.56  38.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0112975000
_diffrn_orient_matrix_UB_12      0.1280239000
_diffrn_orient_matrix_UB_13      -0.0508066000
_diffrn_orient_matrix_UB_21      0.0648439000
_diffrn_orient_matrix_UB_22      0.0268501000
_diffrn_orient_matrix_UB_23      0.0580538000
_diffrn_orient_matrix_UB_31      0.0424370000
_diffrn_orient_matrix_UB_32      -0.0751041000
_diffrn_orient_matrix_UB_33      -0.0659004000
_diffrn_oxdiff_digest_frames     
;
01f0e90135ff7f7bad1705d3c7b7510f07023189ea9
;
_diffrn_oxdiff_digest_hkl        
;
01621570d8187f3ba10e9e68de80a22309bc31
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.753
_reflns_number_gt                2754
_reflns_number_total             2891
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2891
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.039
_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/[σ²(Fo²)+(0.1019P)²+0.9472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1269
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C17(H17), C18(H18), C22(H22),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.27084(4) 0.30309(8) 0.40792(5) 0.0315(3) Uani 1 1 d . . . . .
S5 S 0.43962(18) 0.7180(3) 0.75910(19) 0.0744(7) Uani 1 1 d . . . . .
O8 O 0.3016(3) 0.3625(6) 0.5834(4) 0.0482(11) Uani 1 1 d . . . . .
O9 O 0.3353(3) 0.4834(5) 0.4462(3) 0.0400(10) Uani 1 1 d . . . . .
N10 N 0.6378(3) 0.0877(5) 0.3835(4) 0.0350(12) Uani 1 1 d . . . . .
N13 N 0.7092(3) -0.1151(6) 0.4164(4) 0.0372(12) Uani 1 1 d . . . . .
N16 N 0.4968(3) 0.1684(5) 0.3678(4) 0.0317(11) Uani 1 1 d . . . . .
N19 N 0.3706(3) 0.1933(5) 0.3900(4) 0.0348(12) Uani 1 1 d . . . . .
N21 N 0.6047(3) 0.3618(6) 0.3676(4) 0.0365(11) Uani 1 1 d . . . . .
N24 N 0.6769(3) 0.5679(6) 0.3894(5) 0.0378(12) Uani 1 1 d . . . . .
C2 C 0.3803(4) 0.5818(7) 0.6049(5) 0.0388(14) Uani 1 1 d . . . . .
C3 C 0.4258(5) 0.6976(8) 0.5650(6) 0.0484(18) Uani 1 1 d . . . . .
H3 H 0.430157 0.711451 0.495755 0.058 Uiso 1 1 calc R . . . .
C4 C 0.4672(4) 0.7981(5) 0.6434(4) 0.0244(12) Uani 1 1 d . . . . .
H4 H 0.499016 0.881050 0.633300 0.029 Uiso 1 1 calc R . . . .
C6 C 0.3832(5) 0.5826(8) 0.7089(5) 0.0495(17) Uani 1 1 d . . . . .
H6 H 0.356269 0.513992 0.747323 0.059 Uiso 1 1 calc R . . . .
C7 C 0.3355(4) 0.4677(7) 0.5423(5) 0.0361(13) Uani 1 1 d . . . . .
C11 C 0.6638(4) 0.0921(8) 0.4836(5) 0.0461(17) Uani 1 1 d . . . . .
H11 H 0.653260 0.167434 0.529832 0.055 Uiso 1 1 calc R . . . .
C12 C 0.7067(4) -0.0307(8) 0.5024(6) 0.0471(17) Uani 1 1 d . . . . .
H12 H 0.731216 -0.055102 0.564633 0.057 Uiso 1 1 calc R . . . .
C14 C 0.6664(3) -0.0413(7) 0.3459(5) 0.0325(13) Uani 1 1 d . . . . .
C17 C 0.4774(4) 0.0744(7) 0.4451(5) 0.0386(14) Uani 1 1 d . . . . .
H17 H 0.511598 0.011434 0.481979 0.046 Uiso 1 1 calc R . . . .
C18 C 0.4007(4) 0.0891(7) 0.4580(5) 0.0398(15) Uani 1 1 d . . . . .
H18 H 0.372444 0.037284 0.505291 0.048 Uiso 1 1 calc R . . . .
C20 C 0.4299(3) 0.2388(7) 0.3377(5) 0.0314(12) Uani 1 1 d . . . . .
C22 C 0.5678(4) 0.4568(8) 0.4330(6) 0.0488(17) Uani 1 1 d . . . . .
H22 H 0.520670 0.437946 0.462678 0.059 Uiso 1 1 calc R . . . .
C23 C 0.6119(4) 0.5813(8) 0.4461(7) 0.0495(18) Uani 1 1 d . . . . .
H23 H 0.600374 0.662957 0.486860 0.059 Uiso 1 1 calc R . . . .
C25 C 0.6701(4) 0.4338(7) 0.3432(5) 0.0348(14) Uani 1 1 d . . . . .
C26 C 0.7290(4) 0.3679(10) 0.2755(6) 0.0535(19) Uani 1 1 d . . . . .
H26A H 0.760076 0.447248 0.248939 0.080 Uiso 1 1 calc GR . . . .
H26B H 0.702375 0.315013 0.220614 0.080 Uiso 1 1 calc GR . . . .
H26C H 0.762240 0.299162 0.313647 0.080 Uiso 1 1 calc GR . . . .
C27 C 0.4231(4) 0.3489(8) 0.2521(6) 0.0477(16) Uani 1 1 d . . . . .
H27A H 0.404466 0.443555 0.276426 0.072 Uiso 1 1 calc GR . . . .
H27B H 0.387095 0.310946 0.200268 0.072 Uiso 1 1 calc GR . . . .
H27C H 0.473486 0.362883 0.224664 0.072 Uiso 1 1 calc GR . . . .
C28 C 0.6546(5) -0.0913(9) 0.2399(6) 0.0518(18) Uani 1 1 d . . . . .
H28A H 0.600997 -0.076266 0.217561 0.078 Uiso 1 1 calc GR . . . .
H28B H 0.667489 -0.196212 0.235104 0.078 Uiso 1 1 calc GR . . . .
H28C H 0.687808 -0.033856 0.197843 0.078 Uiso 1 1 calc GR . . . .
B15 B 0.5800(4) 0.2014(7) 0.3315(6) 0.0334(15) Uani 1 1 d . . . . .
H15 H 0.580847 0.193511 0.257558 0.040 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O8 2.411(5) . ?
Cu1 O9 1.995(5) . ?
Cu1 N13 1.981(5) 2_455 ?
Cu1 N19 1.992(5) . ?
Cu1 N24 1.980(5) 2_465 ?
Cu1 C7 2.514(6) . ?
S5 C4 1.771(6) . ?
S5 C6 1.660(8) . ?
O8 C7 1.239(8) . ?
O9 C7 1.278(8) . ?
N10 C11 1.374(9) . ?
N10 C14 1.350(8) . ?
N10 B15 1.551(8) . ?
N13 C12 1.364(9) . ?
N13 C14 1.330(8) . ?
N16 C17 1.372(8) . ?
N16 C20 1.348(8) . ?
N16 B15 1.553(9) . ?
N19 C18 1.372(8) . ?
N19 C20 1.319(8) . ?
N21 C22 1.382(9) . ?
N21 C25 1.343(8) . ?
N21 B15 1.554(8) . ?
N24 C23 1.378(9) . ?
N24 C25 1.340(8) . ?
C2 C3 1.408(10) . ?
C2 C6 1.372(10) . ?
C2 C7 1.495(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.516(8) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.331(10) . ?
C12 H12 0.9300 . ?
C14 C28 1.474(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.340(10) . ?
C18 H18 0.9300 . ?
C20 C27 1.495(9) . ?
C22 H22 0.9300 . ?
C22 C23 1.344(10) . ?
C23 H23 0.9300 . ?
C25 C26 1.500(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
B15 H15 0.9800 . ?

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
O8 Cu1 C7 29.04(19) . . ?
O9 Cu1 O8 59.28(18) . . ?
O9 Cu1 C7 30.2(2) . . ?
N13 Cu1 O8 102.8(2) 2_455 . ?
N13 Cu1 O9 162.0(2) 2_455 . ?
N13 Cu1 N19 93.3(2) 2_455 . ?
N13 Cu1 C7 131.8(2) 2_455 . ?
N19 Cu1 O8 94.2(2) . . ?
N19 Cu1 O9 87.5(2) . . ?
N19 Cu1 C7 91.0(2) . . ?
N24 Cu1 O8 97.5(2) 2_465 . ?
N24 Cu1 O9 90.2(2) 2_465 . ?
N24 Cu1 N13 93.6(2) 2_465 2_455 ?
N24 Cu1 N19 164.8(2) 2_465 . ?
N24 Cu1 C7 94.5(2) 2_465 . ?
C6 S5 C4 96.9(3) . . ?
C7 O8 Cu1 80.1(4) . . ?
C7 O9 Cu1 98.0(4) . . ?
C11 N10 B15 125.3(5) . . ?
C14 N10 C11 105.8(5) . . ?
C14 N10 B15 128.6(5) . . ?
C12 N13 Cu1 123.3(4) . 2 ?
C14 N13 Cu1 130.7(4) . 2 ?
C14 N13 C12 105.9(5) . . ?
C17 N16 B15 127.2(5) . . ?
C20 N16 C17 105.6(5) . . ?
C20 N16 B15 126.9(5) . . ?
C18 N19 Cu1 123.2(5) . . ?
C20 N19 Cu1 126.8(4) . . ?
C20 N19 C18 106.1(5) . . ?
C22 N21 B15 128.7(5) . . ?
C25 N21 C22 105.8(5) . . ?
C25 N21 B15 125.4(5) . . ?
C23 N24 Cu1 123.8(5) . 2_565 ?
C25 N24 Cu1 128.5(4) . 2_565 ?
C25 N24 C23 105.6(5) . . ?
C3 C2 C7 124.5(6) . . ?
C6 C2 C3 112.2(6) . . ?
C6 C2 C7 123.3(6) . . ?
C2 C3 H3 122.5 . . ?
C2 C3 C4 115.0(6) . . ?
C4 C3 H3 122.5 . . ?
S5 C4 H4 128.7 . . ?
C3 C4 S5 102.6(4) . . ?
C3 C4 H4 128.7 . . ?
S5 C6 H6 123.3 . . ?
C2 C6 S5 113.3(6) . . ?
C2 C6 H6 123.3 . . ?
O8 C7 Cu1 70.8(4) . . ?
O8 C7 O9 122.6(6) . . ?
O8 C7 C2 120.5(6) . . ?
O9 C7 Cu1 51.8(3) . . ?
O9 C7 C2 116.9(6) . . ?
C2 C7 Cu1 168.6(5) . . ?
N10 C11 H11 126.1 . . ?
C12 C11 N10 107.9(6) . . ?
C12 C11 H11 126.1 . . ?
N13 C12 H12 125.3 . . ?
C11 C12 N13 109.5(6) . . ?
C11 C12 H12 125.3 . . ?
N10 C14 C28 124.8(6) . . ?
N13 C14 N10 110.9(5) . . ?
N13 C14 C28 124.2(6) . . ?
N16 C17 H17 125.9 . . ?
C18 C17 N16 108.1(6) . . ?
C18 C17 H17 125.9 . . ?
N19 C18 H18 125.7 . . ?
C17 C18 N19 108.6(6) . . ?
C17 C18 H18 125.7 . . ?
N16 C20 C27 124.0(6) . . ?
N19 C20 N16 111.6(5) . . ?
N19 C20 C27 124.4(6) . . ?
N21 C22 H22 125.9 . . ?
C23 C22 N21 108.2(6) . . ?
C23 C22 H22 125.9 . . ?
N24 C23 H23 125.6 . . ?
C22 C23 N24 108.8(6) . . ?
C22 C23 H23 125.6 . . ?
N21 C25 C26 123.5(6) . . ?
N24 C25 N21 111.6(5) . . ?
N24 C25 C26 124.9(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C14 C28 H28A 109.5 . . ?
C14 C28 H28B 109.5 . . ?
C14 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N10 B15 N16 108.4(5) . . ?
N10 B15 N21 107.6(5) . . ?
N10 B15 H15 110.8 . . ?
N16 B15 N21 108.5(5) . . ?
N16 B15 H15 110.8 . . ?
N21 B15 H15 110.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O8 C7 O9 0.0(6) . . . . ?
Cu1 O8 C7 C2 -178.9(6) . . . . ?
Cu1 O9 C7 O8 0.0(7) . . . . ?
Cu1 O9 C7 C2 178.9(4) . . . . ?
Cu1 N13 C12 C11 177.0(5) 2 . . . ?
Cu1 N13 C14 N10 -176.4(4) 2 . . . ?
Cu1 N13 C14 C28 1.3(10) 2 . . . ?
Cu1 N19 C18 C17 -159.0(5) . . . . ?
Cu1 N19 C20 N16 158.6(4) . . . . ?
Cu1 N19 C20 C27 -24.3(9) . . . . ?
Cu1 N24 C23 C22 -164.9(5) 2_565 . . . ?
Cu1 N24 C25 N21 163.7(4) 2_565 . . . ?
Cu1 N24 C25 C26 -14.2(10) 2_565 . . . ?
N10 C11 C12 N13 0.0(9) . . . . ?
N16 C17 C18 N19 -0.5(8) . . . . ?
N21 C22 C23 N24 0.3(9) . . . . ?
C2 C3 C4 S5 1.1(8) . . . . ?
C3 C2 C6 S5 -0.4(9) . . . . ?
C3 C2 C7 Cu1 0(3) . . . . ?
C3 C2 C7 O8 174.5(7) . . . . ?
C3 C2 C7 O9 -4.4(10) . . . . ?
C4 S5 C6 C2 0.9(6) . . . . ?
C6 S5 C4 C3 -1.1(5) . . . . ?
C6 C2 C3 C4 -0.6(10) . . . . ?
C6 C2 C7 Cu1 -178.3(19) . . . . ?
C6 C2 C7 O8 -3.6(10) . . . . ?
C6 C2 C7 O9 177.4(6) . . . . ?
C7 C2 C3 C4 -178.9(6) . . . . ?
C7 C2 C6 S5 178.0(5) . . . . ?
C11 N10 C14 N13 -0.9(7) . . . . ?
C11 N10 C14 C28 -178.5(7) . . . . ?
C11 N10 B15 N16 -73.8(7) . . . . ?
C11 N10 B15 N21 43.3(9) . . . . ?
C12 N13 C14 N10 0.9(7) . . . . ?
C12 N13 C14 C28 178.6(7) . . . . ?
C14 N10 C11 C12 0.5(8) . . . . ?
C14 N10 B15 N16 98.7(7) . . . . ?
C14 N10 B15 N21 -144.2(6) . . . . ?
C14 N13 C12 C11 -0.5(9) . . . . ?
C17 N16 C20 N19 -0.8(7) . . . . ?
C17 N16 C20 C27 -177.9(6) . . . . ?
C17 N16 B15 N10 10.4(8) . . . . ?
C17 N16 B15 N21 -106.1(7) . . . . ?
C18 N19 C20 N16 0.5(7) . . . . ?
C18 N19 C20 C27 177.6(6) . . . . ?
C20 N16 C17 C18 0.8(7) . . . . ?
C20 N16 B15 N10 -177.6(5) . . . . ?
C20 N16 B15 N21 65.9(8) . . . . ?
C20 N19 C18 C17 0.0(8) . . . . ?
C22 N21 C25 N24 0.2(7) . . . . ?
C22 N21 C25 C26 178.2(7) . . . . ?
C22 N21 B15 N10 -108.2(8) . . . . ?
C22 N21 B15 N16 8.8(9) . . . . ?
C23 N24 C25 N21 0.0(8) . . . . ?
C23 N24 C25 C26 -178.0(7) . . . . ?
C25 N21 C22 C23 -0.3(8) . . . . ?
C25 N21 B15 N10 68.8(8) . . . . ?
C25 N21 B15 N16 -174.2(6) . . . . ?
C25 N24 C23 C22 -0.2(9) . . . . ?
B15 N10 C11 C12 174.4(6) . . . . ?
B15 N10 C14 N13 -174.5(6) . . . . ?
B15 N10 C14 C28 7.8(10) . . . . ?
B15 N16 C17 C18 174.1(6) . . . . ?
B15 N16 C20 N19 -174.2(6) . . . . ?
B15 N16 C20 C27 8.7(10) . . . . ?
B15 N21 C22 C23 177.2(7) . . . . ?
B15 N21 C25 N24 -177.4(6) . . . . ?
B15 N21 C25 C26 0.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.265
_oxdiff_exptl_absorpt_empirical_full_min 0.526
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ar14-33
_database_code_depnum_ccdc_archive 'CCDC 2362474'
loop_
_audit_author_name
_audit_author_address
'Hai-Xia Zhang'
;FJIRSM
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 B Cu N6 O2 S'
_chemical_formula_sum            'C17 H19 B Cu N6 O2 S'
_chemical_formula_weight         445.98
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O B S Cu'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.8870 3.6900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4240 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.9474(2)
_cell_length_b                   8.91440(10)
_cell_length_c                   17.0439(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.7990(10)
_cell_angle_gamma                90
_cell_volume                     1960.28(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10783
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      60.0400
_cell_measurement_theta_min      4.5280
_shelx_estimated_absorpt_T_max   0.429
_shelx_estimated_absorpt_T_min   0.235
_exptl_absorpt_coefficient_mu    6.795
_exptl_absorpt_correction_T_max  0.361
_exptl_absorpt_correction_T_min  0.245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16234
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         56.886
_diffrn_reflns_theta_min         4.527
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00 106.00   0.50    0.05    --   76.35 -99.00-150.00  206
  2  ω      2.00 105.00   0.50    0.05    --   76.35 -77.00-120.00  206
  3  ω     20.00 111.00   0.50    0.05    --   76.35-125.00  60.00  182
  4  ω     20.00 111.00   0.50    0.05    --   76.35-125.00 120.00  182
  5  ω      2.00  96.00   0.50    0.05    --   76.35 -57.00 120.00  188
  6  ω      2.00  96.00   0.50    0.05    --   76.35 -57.00  60.00  188
  7  ω     -1.00  71.00   0.50    0.05    --   76.35 -38.00   0.00  144
  8  ω     -1.00  71.00   0.50    0.05    --   76.35 -38.00 -30.00  144
  9  ω     53.00 154.00   0.50    0.05    --   76.35  38.00 -60.00  202
 10  ω     48.00 151.00   0.50    0.05    --   76.35  77.00-180.00  206
 11  ω     54.00 151.00   0.50    0.05    --   76.35  57.00-120.00  194
 12  ω     48.00 151.00   0.50    0.05    --   76.35  77.00 120.00  206
 13  ω    -71.00  -1.00   0.50    0.05    --  -78.22  38.00-120.00  140
 14  ω   -112.00 -20.00   0.50    0.05    --  -78.22 125.00   0.00  184
 15  ω   -112.00 -20.00   0.50    0.05    --  -78.22 125.00-120.00  184
 16  ω    -71.00  -1.00   0.50    0.05    --  -78.22  38.00 -60.00  140
 17  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00 -60.00   92
 18  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00 -90.00   92
 19  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00  60.00   92
 20  ω    -74.00  28.00   0.50    0.05    --   -0.94 -77.00  90.00  204
 21  ω    -74.00  28.00   0.50    0.05    --   -0.94 -77.00 150.00  204
 22  ω   -152.00 -49.00   0.50    0.05    --  -78.22 -77.00  30.00  206
 23  ω   -152.00 -55.00   0.50    0.05    --  -78.22 -57.00  90.00  194
 24  ω    -74.00  21.00   0.50    0.05    --   -0.94 -57.00-150.00  190
 25  ω   -150.00 -79.00   0.50    0.05    --  -78.22-125.00-180.00  142
 26  ω   -152.00 -88.00   0.50    0.05    --  -78.22 -99.00-180.00  128
 27  ω   -152.00 -88.00   0.50    0.05    --  -78.22 -99.00-150.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0937090000
_diffrn_orient_matrix_UB_12      -0.0642398000
_diffrn_orient_matrix_UB_13      0.0024589000
_diffrn_orient_matrix_UB_21      -0.0406058000
_diffrn_orient_matrix_UB_22      -0.1291746000
_diffrn_orient_matrix_UB_23      0.0232274000
_diffrn_orient_matrix_UB_31      -0.0185461000
_diffrn_orient_matrix_UB_32      -0.0419825000
_diffrn_orient_matrix_UB_33      -0.0752971000
_diffrn_oxdiff_digest_frames     
;
01b5232dd3698e17f53841f518ea95c4dd04568aeaf
;
_diffrn_oxdiff_digest_hkl        
;
016c13b453773e4c069f292c5a8280b67f1ef9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.880
_reflns_number_gt                3561
_reflns_number_total             3732
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.010(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3732
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.054
_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/[σ²(Fo²)+(0.0923P)²+0.0598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1209
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{S1, C18}
{S2, C17}
3. Uiso/Uaniso restraints and constraints
Uanis(S1) = Uanis(C18)
Uanis(S2) = Uanis(C17)
4. Others
 Sof(H14A)=Sof(C18)=Sof(H18)=1-FVAR(1)
 Sof(S1)=Sof(H14)=FVAR(1)
 Sof(H16A)=Sof(C17)=Sof(H17)=1-FVAR(2)
 Sof(S2)=Sof(H16)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 B1(H1)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C14(H14), C14(H14A),
 C16(H16), C16(H16A), C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.58515(4) 0.44605(7) 0.72959(4) 0.0161(2) Uani 1 1 d . . . . .
S1 S 0.43684(14) 0.03530(18) 0.56575(11) 0.0243(8) Uani 0.695(14) 1 d . . P A 1
S2 S 0.2638(2) 0.1569(3) 0.6145(2) 0.0286(14) Uani 0.301(14) 1 d . . P A 1
O1 O 0.5462(3) 0.2653(4) 0.6630(2) 0.0205(8) Uani 1 1 d . . . . .
O2 O 0.4055(3) 0.3806(4) 0.6997(2) 0.0240(8) Uani 1 1 d . . . . .
N1 N 0.6001(4) 0.5563(4) 0.6311(3) 0.0195(9) Uani 1 1 d . . . . .
N2 N 0.6062(3) 0.1839(5) 0.3231(3) 0.0187(9) Uani 1 1 d . . . . .
N3 N 0.6251(3) 0.5825(5) 0.5044(3) 0.0178(9) Uani 1 1 d . . . . .
N4 N 0.5761(3) 0.8680(5) 0.2917(3) 0.0190(9) Uani 1 1 d . . . . .
N5 N 0.6098(3) 0.6629(4) 0.3629(3) 0.0173(9) Uani 1 1 d . . . . .
N6 N 0.6275(3) 0.3890(5) 0.3969(3) 0.0180(9) Uani 1 1 d . . . . .
C1 C 0.6563(4) 0.5142(6) 0.5729(3) 0.0166(10) Uani 1 1 d . . . . .
C2 C 0.5443(4) 0.6758(6) 0.5212(3) 0.0200(10) Uani 1 1 d . . . . .
H2 H 0.506027 0.739774 0.484916 0.024 Uiso 1 1 calc R . . . .
C3 C 0.6499(4) 0.3199(6) 0.3303(3) 0.0183(10) Uani 1 1 d . . . . .
C4 C 0.4867(4) 0.7825(6) 0.2911(3) 0.0218(11) Uani 1 1 d . . . . .
H4 H 0.421496 0.808086 0.264738 0.026 Uiso 1 1 calc R . . . .
C5 C 0.6489(4) 0.7923(6) 0.3356(3) 0.0170(10) Uani 1 1 d . . . . .
C6 C 0.5296(4) 0.6599(6) 0.5981(3) 0.0212(11) Uani 1 1 d . . . . .
H6 H 0.479082 0.711383 0.625223 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5070(4) 0.6574(6) 0.3339(3) 0.0220(11) Uani 1 1 d . . . . .
H7 H 0.459295 0.579418 0.342519 0.026 Uiso 1 1 calc R . . . .
C8 C 0.5533(5) 0.1666(6) 0.3896(3) 0.0237(11) Uani 1 1 d . . . . .
H8 H 0.514949 0.080105 0.401825 0.028 Uiso 1 1 calc R . . . .
C9 C 0.7575(4) 0.8428(6) 0.3500(4) 0.0251(12) Uani 1 1 d . . . . .
H9A H 0.799346 0.796936 0.311137 0.038 Uiso 1 1 calc GR . . . .
H9B H 0.784686 0.812627 0.403080 0.038 Uiso 1 1 calc GR . . . .
H9C H 0.760451 0.952234 0.345433 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.5643(4) 0.2908(6) 0.4347(3) 0.0214(10) Uani 1 1 d . . . . .
H10 H 0.534589 0.308063 0.483031 0.026 Uiso 1 1 calc R . . . .
C11 C 0.3836(4) 0.1642(6) 0.6194(3) 0.0218(11) Uani 1 1 d . . . . .
C12 C 0.4476(4) 0.2781(5) 0.6640(3) 0.0187(10) Uani 1 1 d . . . . .
C13 C 0.7131(5) 0.3907(6) 0.2702(3) 0.0248(11) Uani 1 1 d . . . . .
H13A H 0.735750 0.313179 0.234677 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.773846 0.440041 0.296948 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.670808 0.465104 0.239797 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.3270(6) -0.0431(6) 0.5350(4) 0.0322(14) Uani 1 1 d . . . . .
H14 H 0.322233 -0.127636 0.500908 0.039 Uiso 0.695(14) 1 calc R . P A 1
H14A H 0.322233 -0.127636 0.500908 0.039 Uiso 0.305(14) 1 calc R . P A 2
C15 C 0.7436(4) 0.4047(6) 0.5831(3) 0.0217(11) Uani 1 1 d . . . . .
H15A H 0.789329 0.431871 0.629666 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.782844 0.406651 0.536420 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.715828 0.303693 0.589978 0.033 Uiso 1 1 calc GR . . . .
C16 C 0.2428(5) 0.0236(7) 0.5626(4) 0.0363(16) Uani 1 1 d . . . . .
H16 H 0.174473 -0.012644 0.549638 0.044 Uiso 0.301(14) 1 calc R . P A 1
H16A H 0.174473 -0.012644 0.549638 0.044 Uiso 0.699(14) 1 calc R . P A 2
C17 C 0.2638(2) 0.1569(3) 0.6145(2) 0.0286(14) Uani 0.699(14) 1 d . . P A 2
H17 H 0.216286 0.220336 0.638167 0.034 Uiso 0.699(14) 1 calc R . P A 2
C18 C 0.43684(14) 0.03530(18) 0.56575(11) 0.0243(8) Uani 0.305(14) 1 d . . P A
2
H18 H 0.506638 0.014353 0.556221 0.029 Uiso 0.305(14) 1 calc R . P A 2
B1 B 0.6628(5) 0.5501(6) 0.4220(4) 0.0163(11) Uani 1 1 d . . . . .
H1 H 0.739921 0.559302 0.423406 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O1 2.010(4) . ?
Cu1 O2 2.411(4) . ?
Cu1 N1 1.968(5) . ?
Cu1 N2 1.970(4) 4_455 ?
Cu1 N4 1.976(4) 4_465 ?
Cu1 C12 2.516(5) . ?
S1 C11 1.655(6) . ?
S1 C14 1.632(7) . ?
S2 C11 1.548(6) . ?
S2 C16 1.493(8) . ?
O1 C12 1.282(7) . ?
O2 C12 1.248(7) . ?
N1 C1 1.332(7) . ?
N1 C6 1.385(7) . ?
N2 C3 1.339(7) . ?
N2 C8 1.382(7) . ?
N3 C1 1.348(7) . ?
N3 C2 1.384(7) . ?
N3 B1 1.553(7) . ?
N4 C4 1.385(7) . ?
N4 C5 1.337(7) . ?
N5 C5 1.357(6) . ?
N5 C7 1.381(7) . ?
N5 B1 1.543(7) . ?
N6 C3 1.345(7) . ?
N6 C10 1.393(7) . ?
N6 B1 1.556(7) . ?
C1 C15 1.492(7) . ?
C2 C6 1.347(8) . ?
C3 C13 1.501(8) . ?
C4 C7 1.346(8) . ?
C5 C9 1.478(7) . ?
C8 C10 1.348(8) . ?
C11 C12 1.480(7) . ?
C11 C17 1.548(6) . ?
C11 C18 1.655(6) . ?
C14 C16 1.360(10) . ?
C14 C18 1.632(7) . ?
C16 C17 1.493(8) . ?

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
O1 Cu1 O2 59.64(14) . . ?
O1 Cu1 C12 30.38(16) . . ?
O2 Cu1 C12 29.26(15) . . ?
N1 Cu1 O1 87.52(17) . . ?
N1 Cu1 O2 95.90(17) . . ?
N1 Cu1 N2 165.04(19) . 4_455 ?
N1 Cu1 N4 92.99(19) . 4_465 ?
N1 Cu1 C12 91.99(18) . . ?
N2 Cu1 O1 89.80(17) 4_455 . ?
N2 Cu1 O2 95.42(16) 4_455 . ?
N2 Cu1 N4 94.06(18) 4_455 4_465 ?
N2 Cu1 C12 93.12(17) 4_455 . ?
N4 Cu1 O1 162.06(16) 4_465 . ?
N4 Cu1 O2 102.52(16) 4_465 . ?
N4 Cu1 C12 131.75(17) 4_465 . ?
C14 S1 C11 94.8(3) . . ?
C16 S2 C11 101.4(4) . . ?
C12 O1 Cu1 97.2(3) . . ?
C12 O2 Cu1 80.0(3) . . ?
C1 N1 Cu1 126.4(3) . . ?
C1 N1 C6 105.5(5) . . ?
C6 N1 Cu1 124.8(4) . . ?
C3 N2 Cu1 129.4(4) . 4_454 ?
C3 N2 C8 105.1(4) . . ?
C8 N2 Cu1 123.6(3) . 4_454 ?
C1 N3 C2 105.6(4) . . ?
C1 N3 B1 127.2(4) . . ?
C2 N3 B1 126.8(4) . . ?
C4 N4 Cu1 123.0(4) . 4_464 ?
C5 N4 Cu1 130.8(4) . 4_464 ?
C5 N4 C4 106.0(4) . . ?
C5 N5 C7 106.4(4) . . ?
C5 N5 B1 128.2(4) . . ?
C7 N5 B1 125.0(4) . . ?
C3 N6 C10 106.2(4) . . ?
C3 N6 B1 125.1(4) . . ?
C10 N6 B1 128.6(4) . . ?
N1 C1 N3 112.0(4) . . ?
N1 C1 C15 123.6(5) . . ?
N3 C1 C15 124.4(5) . . ?
C6 C2 N3 108.0(5) . . ?
N2 C3 N6 111.9(5) . . ?
N2 C3 C13 124.6(5) . . ?
N6 C3 C13 123.5(5) . . ?
C7 C4 N4 109.0(5) . . ?
N4 C5 N5 110.8(4) . . ?
N4 C5 C9 123.8(5) . . ?
N5 C5 C9 125.4(5) . . ?
C2 C6 N1 108.9(5) . . ?
C4 C7 N5 107.7(4) . . ?
C10 C8 N2 109.9(5) . . ?
C8 C10 N6 106.9(5) . . ?
S2 C11 S1 113.7(4) . . ?
C12 C11 S1 121.2(4) . . ?
C12 C11 S2 125.0(4) . . ?
C12 C11 C17 125.0(4) . . ?
C12 C11 C18 121.2(4) . . ?
C17 C11 C18 113.7(4) . . ?
O1 C12 Cu1 52.5(2) . . ?
O1 C12 C11 116.6(5) . . ?
O2 C12 Cu1 70.7(3) . . ?
O2 C12 O1 123.1(5) . . ?
O2 C12 C11 120.2(5) . . ?
C11 C12 Cu1 169.1(4) . . ?
C16 C14 S1 113.8(5) . . ?
C16 C14 C18 113.8(5) . . ?
C14 C16 S2 116.2(5) . . ?
C14 C16 C17 116.2(5) . . ?
C16 C17 C11 101.4(4) . . ?
C14 C18 C11 94.8(3) . . ?
N3 B1 N6 108.2(4) . . ?
N5 B1 N3 108.2(4) . . ?
N5 B1 N6 108.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.991
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ar15-41cl
_database_code_depnum_ccdc_archive 'CCDC 2362476'
loop_
_audit_author_name
_audit_author_address
'Hai-Xia Zhang'
;FJIRSM
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 B Cu N6 O3'
_chemical_formula_sum            'C18 H19 B Cu N6 O3'
_chemical_formula_weight         429.74
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O B Cu'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.8870 3.6900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.6893(3)
_cell_length_b                   8.8027(2)
_cell_length_c                   17.1269(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.777(2)
_cell_angle_gamma                90
_cell_volume                     1910.83(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13026
_cell_measurement_temperature    103.2(4)
_cell_measurement_theta_max      55.0280
_cell_measurement_theta_min      4.4960
_shelx_estimated_absorpt_T_max   0.452
_shelx_estimated_absorpt_T_min   0.254
_exptl_absorpt_coefficient_mu    6.299
_exptl_absorpt_correction_T_max  0.389
_exptl_absorpt_correction_T_min  0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        52.928
_diffrn_reflns_theta_max         52.928
_diffrn_reflns_theta_min         4.494
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103.2(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  72.00   0.50    0.10    --   -1.41  38.00 -30.00  176
  2  ω    -74.00  15.00   0.50    0.10    --   -1.41 -57.00-180.00  178
  3  ω     20.00 110.00   0.50    0.25    --   61.59-125.00-150.00  180
  4  ω     46.00 135.00   0.50    0.25    --   61.59  57.00  60.00  178
  5  ω    -14.00  26.00   0.50    0.25    --   61.59 -19.00 120.00   80
  6  ω     -8.00  96.00   0.50    0.25    --   61.59 -99.00 120.00  208
  7  ω    -11.00  85.00   0.50    0.25    --   61.59 -77.00 -60.00  192
  8  ω     79.00 135.00   0.50    0.25    --   61.59 125.00-120.00  112
  9  ω    -11.00  66.00   0.50    0.25    --   61.59 -57.00-120.00  154
 10  ω     -8.00  96.00   0.50    0.25    --   61.59 -99.00-150.00  208
 11  ω     46.00 135.00   0.50    0.25    --   61.59  57.00  30.00  178
 12  ω    -66.00   9.00   0.50    0.25    --  -64.40  57.00   0.00  150
 13  ω   -137.00 -48.00   0.50    0.25    --  -64.40 -57.00-150.00  178
 14  ω   -111.00 -20.00   0.50    0.25    --  -64.40 125.00  30.00  182
 15  ω    -25.00  72.00   0.50    0.10    --   -1.41  77.00 -30.00  194
 16  ω    -74.00  22.00   0.50    0.10    --   -1.41 -77.00 -90.00  192
 17  ω     38.00 135.00   0.50    0.25    --   61.59  77.00 -30.00  194
 18  ω     38.00 135.00   0.50    0.25    --   61.59  77.00-180.00  194
 19  ω     38.00  65.00   0.50    0.25    --   61.59  77.00 -90.00   54
 20  ω     38.00 135.00   0.50    0.25    --   61.59  77.00  90.00  194
 21  ω     38.00 135.00   0.50    0.25    --   61.59  77.00 120.00  194
 22  ω   -137.00 -41.00   0.50    0.25    --  -64.40 -77.00 -60.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0109285000
_diffrn_orient_matrix_UB_12      0.0703002000
_diffrn_orient_matrix_UB_13      0.0684499000
_diffrn_orient_matrix_UB_21      -0.0894675000
_diffrn_orient_matrix_UB_22      -0.0772714000
_diffrn_orient_matrix_UB_23      0.0097872000
_diffrn_orient_matrix_UB_31      0.0550761000
_diffrn_orient_matrix_UB_32      -0.1106892000
_diffrn_orient_matrix_UB_33      0.0366857000
_diffrn_oxdiff_digest_frames     
;
0104bc420e7c953fe7689962ab746b6d0503762750b
;
_diffrn_oxdiff_digest_hkl        
;
01509fec6d822a14d3864d6cbe24ef89483a5b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3272
_reflns_number_total             3360
_reflns_odcompleteness_completeness 93.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1537 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.044
_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/[σ²(Fo²)+(0.0415P)²+1.6458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C19(H19), C20(H20), C22(H22),
 C23(H23)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.58190(3) 0.55837(5) 0.39404(3) 0.01326(14) Uani 1 1 d . . . . .
O6 O 0.4222(2) 0.9437(3) 0.23493(18) 0.0323(7) Uani 1 1 d . . . . .
O8 O 0.4022(2) 0.6218(3) 0.36227(15) 0.0208(6) Uani 1 1 d . . . . .
O9 O 0.54611(19) 0.7402(3) 0.32569(14) 0.0166(5) Uani 1 1 d . . . . .
N10 N 0.6262(2) -0.1065(3) 0.56256(17) 0.0149(6) Uani 1 1 d . . . . .
N12 N 0.6011(2) -0.3099(3) 0.48707(18) 0.0167(7) Uani 1 1 d . . . . .
N16 N 0.6260(2) 0.0879(3) 0.67100(17) 0.0141(6) Uani 1 1 d . . . . .
N18 N 0.6013(2) 0.0586(3) 0.79717(18) 0.0141(6) Uani 1 1 d . . . . .
N21 N 0.6064(2) 0.1693(3) 0.53089(17) 0.0149(6) Uani 1 1 d . . . . .
N24 N 0.5704(2) 0.3726(3) 0.45811(17) 0.0163(6) Uani 1 1 d . . . . .
C2 C 0.3806(3) 0.8369(4) 0.2818(2) 0.0173(7) Uani 1 1 d . . . . .
C3 C 0.2746(3) 0.8495(4) 0.2817(2) 0.0143(7) Uani 1 1 d . . . . .
H3 H 0.228797 0.789708 0.309348 0.017 Uiso 1 1 calc R . . . .
C4 C 0.2471(4) 0.9715(5) 0.2314(3) 0.0322(10) Uani 1 1 d . . . . .
H4 H 0.179335 1.007612 0.219468 0.039 Uiso 1 1 calc R . . . .
C5 C 0.3369(4) 1.0257(5) 0.2041(3) 0.0310(10) Uani 1 1 d . . . . .
H5 H 0.341295 1.106492 0.169391 0.037 Uiso 1 1 calc R . . . .
C7 C 0.4465(3) 0.7258(4) 0.3263(2) 0.0153(7) Uani 1 1 d . . . . .
C11 C 0.6463(3) -0.1729(4) 0.4936(2) 0.0147(7) Uani 1 1 d . . . . .
C13 C 0.5491(3) -0.3303(4) 0.5556(2) 0.0191(8) Uani 1 1 d . . . . .
H13 H 0.510121 -0.415859 0.567814 0.023 Uiso 1 1 calc R . . . .
C14 C 0.5634(3) -0.2080(4) 0.6016(2) 0.0177(8) Uani 1 1 d . . . . .
H14 H 0.536277 -0.193707 0.650584 0.021 Uiso 1 1 calc R . . . .
C17 C 0.6578(3) 0.0152(4) 0.7375(2) 0.0138(7) Uani 1 1 d . . . . .
C19 C 0.5310(3) 0.1666(4) 0.7679(2) 0.0166(8) Uani 1 1 d . . . . .
H19 H 0.481561 0.217956 0.796287 0.020 Uiso 1 1 calc R . . . .
C20 C 0.5463(3) 0.1850(4) 0.6907(2) 0.0167(7) Uani 1 1 d . . . . .
H20 H 0.509501 0.251252 0.656959 0.020 Uiso 1 1 calc R . . . .
C22 C 0.5012(3) 0.1622(4) 0.5054(2) 0.0190(8) Uani 1 1 d . . . . .
H22 H 0.453811 0.085595 0.516800 0.023 Uiso 1 1 calc R . . . .
C23 C 0.4798(3) 0.2854(4) 0.4613(2) 0.0186(8) Uani 1 1 d . . . . .
H23 H 0.414771 0.308495 0.436827 0.022 Uiso 1 1 calc R . . . .
C25 C 0.6450(3) 0.2997(4) 0.5006(2) 0.0140(7) Uani 1 1 d . . . . .
C26 C 0.7551(3) 0.3531(4) 0.5119(2) 0.0209(8) Uani 1 1 d . . . . .
H26A H 0.798270 0.302768 0.475380 0.031 Uiso 1 1 calc GR . . . .
H26B H 0.780828 0.330427 0.564250 0.031 Uiso 1 1 calc GR . . . .
H26C H 0.757643 0.460834 0.503488 0.031 Uiso 1 1 calc GR . . . .
C27 C 0.7451(3) -0.0970(4) 0.7439(2) 0.0187(8) Uani 1 1 d . . . . .
H27A H 0.791449 -0.072028 0.788022 0.028 Uiso 1 1 calc GR . . . .
H27B H 0.783705 -0.094663 0.697134 0.028 Uiso 1 1 calc GR . . . .
H27C H 0.716484 -0.196776 0.750839 0.028 Uiso 1 1 calc GR . . . .
C28 C 0.7087(3) -0.0994(4) 0.4326(2) 0.0198(8) Uani 1 1 d . . . . .
H28A H 0.733888 -0.175611 0.398000 0.030 Uiso 1 1 calc GR . . . .
H28B H 0.767634 -0.046473 0.457084 0.030 Uiso 1 1 calc GR . . . .
H28C H 0.664832 -0.028644 0.403327 0.030 Uiso 1 1 calc GR . . . .
B15 B 0.6630(3) 0.0559(4) 0.5873(2) 0.0157(8) Uani 1 1 d . . . . .
H15 H 0.739790 0.065675 0.585496 0.019 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O8 2.385(3) . ?
Cu1 O9 2.022(3) . ?
Cu1 N12 1.976(3) 1_565 ?
Cu1 N18 1.978(3) 4_454 ?
Cu1 N24 1.978(3) . ?
Cu1 C7 2.505(4) . ?
O6 C2 1.359(5) . ?
O6 C5 1.384(5) . ?
O8 C7 1.252(4) . ?
O9 C7 1.271(4) . ?
N10 C11 1.353(5) . ?
N10 C14 1.390(4) . ?
N10 B15 1.556(5) . ?
N12 C11 1.338(5) . ?
N12 C13 1.386(5) . ?
N16 C17 1.351(5) . ?
N16 C20 1.379(5) . ?
N16 B15 1.556(5) . ?
N18 C17 1.333(5) . ?
N18 C19 1.382(5) . ?
N21 C22 1.386(5) . ?
N21 C25 1.361(4) . ?
N21 B15 1.542(5) . ?
N24 C23 1.386(5) . ?
N24 C25 1.330(5) . ?
C2 C3 1.350(5) . ?
C2 C7 1.475(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.410(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.341(7) . ?
C5 H5 0.9300 . ?
C11 C28 1.489(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.342(5) . ?
C14 H14 0.9300 . ?
C17 C27 1.483(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.355(5) . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.342(5) . ?
C23 H23 0.9300 . ?
C25 C26 1.478(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
B15 H15 0.9800 . ?

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
O8 Cu1 C7 29.53(10) . . ?
O9 Cu1 O8 59.81(9) . . ?
O9 Cu1 C7 30.28(11) . . ?
N12 Cu1 O8 97.25(11) 1_565 . ?
N12 Cu1 O9 91.03(12) 1_565 . ?
N12 Cu1 N18 165.03(12) 1_565 4_454 ?
N12 Cu1 N24 92.70(12) 1_565 . ?
N12 Cu1 C7 94.79(12) 1_565 . ?
N18 Cu1 O8 95.00(11) 4_454 . ?
N18 Cu1 O9 87.71(11) 4_454 . ?
N18 Cu1 N24 92.90(13) 4_454 . ?
N18 Cu1 C7 91.62(11) 4_454 . ?
N24 Cu1 O8 102.99(11) . . ?
N24 Cu1 O9 162.75(11) . . ?
N24 Cu1 C7 132.51(12) . . ?
C2 O6 C5 105.5(3) . . ?
C7 O8 Cu1 80.6(2) . . ?
C7 O9 Cu1 96.4(2) . . ?
C11 N10 C14 106.2(3) . . ?
C11 N10 B15 124.6(3) . . ?
C14 N10 B15 129.1(3) . . ?
C11 N12 Cu1 129.2(2) . 1_545 ?
C11 N12 C13 105.4(3) . . ?
C13 N12 Cu1 124.1(2) . 1_545 ?
C17 N16 C20 106.3(3) . . ?
C17 N16 B15 126.9(3) . . ?
C20 N16 B15 126.5(3) . . ?
C17 N18 Cu1 126.0(2) . 4_455 ?
C17 N18 C19 106.3(3) . . ?
C19 N18 Cu1 123.9(2) . 4_455 ?
C22 N21 B15 125.5(3) . . ?
C25 N21 C22 106.1(3) . . ?
C25 N21 B15 128.3(3) . . ?
C23 N24 Cu1 124.3(2) . . ?
C25 N24 Cu1 129.3(3) . . ?
C25 N24 C23 106.3(3) . . ?
O6 C2 C7 122.5(3) . . ?
C3 C2 O6 111.0(3) . . ?
C3 C2 C7 126.5(3) . . ?
C2 C3 H3 126.9 . . ?
C2 C3 C4 106.3(3) . . ?
C4 C3 H3 126.9 . . ?
C3 C4 H4 126.4 . . ?
C5 C4 C3 107.2(4) . . ?
C5 C4 H4 126.4 . . ?
O6 C5 H5 125.0 . . ?
C4 C5 O6 110.1(4) . . ?
C4 C5 H5 125.0 . . ?
O8 C7 Cu1 69.90(19) . . ?
O8 C7 O9 123.2(3) . . ?
O8 C7 C2 118.8(3) . . ?
O9 C7 Cu1 53.30(17) . . ?
O9 C7 C2 118.0(3) . . ?
C2 C7 Cu1 171.2(2) . . ?
N10 C11 C28 123.6(3) . . ?
N12 C11 N10 111.4(3) . . ?
N12 C11 C28 125.0(3) . . ?
N12 C13 H13 125.2 . . ?
C14 C13 N12 109.7(3) . . ?
C14 C13 H13 125.2 . . ?
N10 C14 H14 126.4 . . ?
C13 C14 N10 107.3(3) . . ?
C13 C14 H14 126.4 . . ?
N16 C17 C27 124.7(3) . . ?
N18 C17 N16 111.2(3) . . ?
N18 C17 C27 124.1(3) . . ?
N18 C19 H19 125.8 . . ?
C20 C19 N18 108.5(3) . . ?
C20 C19 H19 125.8 . . ?
N16 C20 H20 126.1 . . ?
C19 C20 N16 107.8(3) . . ?
C19 C20 H20 126.1 . . ?
N21 C22 H22 126.1 . . ?
C23 C22 N21 107.8(3) . . ?
C23 C22 H22 126.1 . . ?
N24 C23 H23 125.5 . . ?
C22 C23 N24 109.0(3) . . ?
C22 C23 H23 125.5 . . ?
N21 C25 C26 125.0(3) . . ?
N24 C25 N21 110.9(3) . . ?
N24 C25 C26 124.1(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C17 C27 H27A 109.5 . . ?
C17 C27 H27B 109.5 . . ?
C17 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C11 C28 H28A 109.5 . . ?
C11 C28 H28B 109.5 . . ?
C11 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N10 B15 H15 110.9 . . ?
N16 B15 N10 108.5(3) . . ?
N16 B15 H15 110.9 . . ?
N21 B15 N10 107.4(3) . . ?
N21 B15 N16 107.9(3) . . ?
N21 B15 H15 110.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O8 C7 O9 0.1(3) . . . . ?
Cu1 O8 C7 C2 179.6(3) . . . . ?
Cu1 O9 C7 O8 -0.1(4) . . . . ?
Cu1 O9 C7 C2 -179.6(3) . . . . ?
Cu1 N12 C11 N10 168.0(2) 1_545 . . . ?
Cu1 N12 C11 C28 -10.6(5) 1_545 . . . ?
Cu1 N12 C13 C14 -168.4(3) 1_545 . . . ?
Cu1 N18 C17 N16 157.5(2) 4_455 . . . ?
Cu1 N18 C17 C27 -23.2(5) 4_455 . . . ?
Cu1 N18 C19 C20 -158.7(3) 4_455 . . . ?
Cu1 N24 C23 C22 175.4(2) . . . . ?
Cu1 N24 C25 N21 -175.0(2) . . . . ?
Cu1 N24 C25 C26 4.1(5) . . . . ?
O6 C2 C3 C4 0.2(4) . . . . ?
O6 C2 C7 O8 -173.2(3) . . . . ?
O6 C2 C7 O9 6.4(5) . . . . ?
N12 C13 C14 N10 -0.3(4) . . . . ?
N18 C19 C20 N16 0.3(4) . . . . ?
N21 C22 C23 N24 -0.1(4) . . . . ?
C2 O6 C5 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C2 C7 O8 7.5(5) . . . . ?
C3 C2 C7 O9 -172.9(3) . . . . ?
C3 C4 C5 O6 -0.2(5) . . . . ?
C5 O6 C2 C3 -0.3(4) . . . . ?
C5 O6 C2 C7 -179.8(3) . . . . ?
C7 C2 C3 C4 179.6(3) . . . . ?
C11 N10 C14 C13 0.5(4) . . . . ?
C11 N10 B15 N16 -178.8(3) . . . . ?
C11 N10 B15 N21 64.7(4) . . . . ?
C11 N12 C13 C14 -0.1(4) . . . . ?
C13 N12 C11 N10 0.5(4) . . . . ?
C13 N12 C11 C28 -178.1(3) . . . . ?
C14 N10 C11 N12 -0.6(4) . . . . ?
C14 N10 C11 C28 178.0(3) . . . . ?
C14 N10 B15 N16 5.3(5) . . . . ?
C14 N10 B15 N21 -111.2(4) . . . . ?
C17 N16 C20 C19 -0.9(4) . . . . ?
C17 N16 B15 N10 64.8(4) . . . . ?
C17 N16 B15 N21 -179.1(3) . . . . ?
C17 N18 C19 C20 0.5(4) . . . . ?
C19 N18 C17 N16 -1.1(4) . . . . ?
C19 N18 C17 C27 178.2(3) . . . . ?
C20 N16 C17 N18 1.3(4) . . . . ?
C20 N16 C17 C27 -178.0(3) . . . . ?
C20 N16 B15 N10 -107.8(4) . . . . ?
C20 N16 B15 N21 8.4(5) . . . . ?
C22 N21 C25 N24 -0.1(4) . . . . ?
C22 N21 C25 C26 -179.3(3) . . . . ?
C22 N21 B15 N10 42.4(4) . . . . ?
C22 N21 B15 N16 -74.4(4) . . . . ?
C23 N24 C25 N21 0.0(4) . . . . ?
C23 N24 C25 C26 179.2(3) . . . . ?
C25 N21 C22 C23 0.1(4) . . . . ?
C25 N21 B15 N10 -142.5(3) . . . . ?
C25 N21 B15 N16 100.7(4) . . . . ?
C25 N24 C23 C22 0.0(4) . . . . ?
B15 N10 C11 N12 -177.3(3) . . . . ?
B15 N10 C11 C28 1.3(5) . . . . ?
B15 N10 C14 C13 177.0(3) . . . . ?
B15 N16 C17 N18 -172.5(3) . . . . ?
B15 N16 C17 C27 8.2(6) . . . . ?
B15 N16 C20 C19 172.9(3) . . . . ?
B15 N21 C22 C23 176.1(3) . . . . ?
B15 N21 C25 N24 -175.9(3) . . . . ?
B15 N21 C25 C26 4.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.305
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ar14-38cl
_database_code_depnum_ccdc_archive 'CCDC 2362475'
loop_
_audit_author_name
_audit_author_address
'Hai-Xia Zhang'
;FJIRSM
China
;
_audit_update_record             
;
2024-06-13 deposited with the CCDC.	2024-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 B Cu N6 O3'
_chemical_formula_sum            'C17 H19 B Cu N6 O3'
_chemical_formula_weight         429.73
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O B Cu'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0150 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0070 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -2.8870 3.6900 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'I a'
_space_group_name_Hall           'I -2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z'
'x+1/2, y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   12.5552(2)
_cell_length_b                   8.81030(10)
_cell_length_c                   17.1609(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.0380(10)
_cell_angle_gamma                90
_cell_volume                     1897.05(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14542
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      59.9920
_cell_measurement_theta_min      5.3100
_shelx_estimated_absorpt_T_max   0.448
_shelx_estimated_absorpt_T_min   0.251
_exptl_absorpt_coefficient_mu    6.374
_exptl_absorpt_correction_T_max  0.384
_exptl_absorpt_correction_T_min  0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear bluish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16779
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        53.543
_diffrn_reflns_theta_max         56.904
_diffrn_reflns_theta_min         4.483
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -20.00   0.50    0.05    --  -78.22 125.00  90.00  184
  2  ω   -107.00  -4.00   0.50    0.05    --  -78.22  77.00  60.00  206
  3  ω   -107.00  -4.00   0.50    0.05    --  -78.22  77.00 -30.00  206
  4  ω    -88.00   3.00   0.50    0.05    --  -78.22  20.00  21.00  182
  5  ω    -31.00  80.00   0.50    0.05    --   -0.94  20.00  21.00  222
  6  ω    -74.00  28.00   0.50    0.05    --   -0.94 -77.00-120.00  204
  7  ω    -80.00  29.00   0.50    0.05    --   -0.94 -20.00-145.00  218
  8  ω   -159.00 -48.00   0.50    0.05    --  -78.22 -20.00-145.00  222
  9  ω    -74.00  28.00   0.50    0.05    --   -0.94 -77.00 150.00  204
 10  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00  30.00   92
 11  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00 -30.00   92
 12  ω   -150.00 -79.00   0.50    0.05    --  -78.22-125.00 -30.00  142
 13  ω     -8.00  38.00   0.50    0.05    --   -0.94 -99.00-180.00   92
 14  ω     -4.00  88.00   0.50    0.05    --   76.35 -20.00-145.00  184
 15  ω     79.00 148.00   0.50    0.05    --   76.35 125.00 150.00  138
 16  ω     79.00 148.00   0.50    0.05    --   76.35 125.00-150.00  138
 17  ω     -1.00  71.00   0.50    0.05    --   76.35 -38.00-150.00  144
 18  ω      2.00 105.00   0.50    0.05    --   76.35 -77.00-180.00  206
 19  ω     47.00 157.00   0.50    0.05    --   76.35  20.00  21.00  220
 20  ω     48.00 151.00   0.50    0.05    --   76.35  77.00 -90.00  206
 21  ω     48.00  77.00   0.50    0.05    --   76.35  77.00-180.00   58
 22  ω     48.00 151.00   0.50    0.05    --   76.35  77.00  30.00  206
 23  ω     54.00 151.00   0.50    0.05    --   76.35  57.00 120.00  194
 24  ω     20.00 111.00   0.50    0.05    --   76.35-125.00-150.00  182
 25  ω      3.00 106.00   0.50    0.05    --   76.35 -99.00-120.00  206
 26  ω      3.00 106.00   0.50    0.05    --   76.35 -99.00 -60.00  206
 27  ω     20.00 111.00   0.50    0.05    --   76.35-125.00  90.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1061982000
_diffrn_orient_matrix_UB_12      -0.0080074000
_diffrn_orient_matrix_UB_13      0.0095785000
_diffrn_orient_matrix_UB_21      -0.0034240000
_diffrn_orient_matrix_UB_22      -0.1477968000
_diffrn_orient_matrix_UB_23      -0.0183588000
_diffrn_orient_matrix_UB_31      0.0103779000
_diffrn_orient_matrix_UB_32      0.0348448000
_diffrn_orient_matrix_UB_33      -0.0752430000
_diffrn_oxdiff_digest_frames     
;
013aaf3ee78828e59f224c18a6f9d3249404736ae39
;
_diffrn_oxdiff_digest_hkl        
;
01459fb7c339f540299ecbf14517307d8b6f7c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.3405
_diffrn_source                   'micro-focus metaljet'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.853
_reflns_Friedel_fraction_max     0.847
_reflns_number_gt                3441
_reflns_number_total             3566
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     56.82
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.012(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.050
_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/[σ²(Fo²)+(0.0823P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 B1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C17(H17)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57610(3) 0.44006(5) 0.73132(3) 0.01354(17) Uani 1 1 d . . . . .
O1 O 0.5435(2) 0.2582(3) 0.66448(17) 0.0181(6) Uani 1 1 d . . . . .
O2 O 0.3926(2) 0.3707(3) 0.69625(17) 0.0217(6) Uani 1 1 d . . . . .
O3 O 0.3530(3) -0.0471(4) 0.5371(3) 0.0378(9) Uani 1 1 d . . . . .
N1 N 0.6172(3) 0.5870(4) 0.5074(2) 0.0146(6) Uani 1 1 d . . . . .
N2 N 0.5943(3) 0.5563(3) 0.6344(2) 0.0149(7) Uani 1 1 d . . . . .
N3 N 0.5944(3) 0.1917(4) 0.32395(19) 0.0158(7) Uani 1 1 d . . . . .
N4 N 0.5632(3) 0.8745(4) 0.2954(2) 0.0167(7) Uani 1 1 d . . . . .
N5 N 0.5989(3) 0.6716(4) 0.36843(19) 0.0148(6) Uani 1 1 d . . . . .
N6 N 0.6181(3) 0.3952(4) 0.39870(19) 0.0156(6) Uani 1 1 d . . . . .
C1 C 0.6509(3) 0.5147(4) 0.5736(2) 0.0145(7) Uani 1 1 d . . . . .
C2 C 0.5411(3) 0.1709(4) 0.3922(2) 0.0188(8) Uani 1 1 d . . . . .
H2 H 0.501219 0.083234 0.404954 0.023 Uiso 1 1 calc R . . . .
C3 C 0.4722(3) 0.7876(4) 0.2982(2) 0.0189(8) Uani 1 1 d . . . . .
H3 H 0.405621 0.811166 0.273099 0.023 Uiso 1 1 calc R . . . .
C4 C 0.5213(3) 0.6628(4) 0.6056(2) 0.0170(8) Uani 1 1 d . . . . .
H4 H 0.470152 0.714419 0.635351 0.020 Uiso 1 1 calc R . . . .
C5 C 0.6380(3) 0.8022(4) 0.3387(2) 0.0151(8) Uani 1 1 d . . . . .
C6 C 0.7042(3) 0.4029(5) 0.2692(2) 0.0197(8) Uani 1 1 d . . . . .
H6A H 0.728251 0.325858 0.232594 0.030 Uiso 1 1 calc GR . . . .
H6B H 0.766156 0.453360 0.293941 0.030 Uiso 1 1 calc GR . . . .
H6C H 0.660119 0.478141 0.240946 0.030 Uiso 1 1 calc GR . . . .
C7 C 0.6402(3) 0.3291(4) 0.3301(2) 0.0146(7) Uani 1 1 d . . . . .
C8 C 0.4929(3) 0.6629(4) 0.3425(2) 0.0191(8) Uani 1 1 d . . . . .
H8 H 0.444100 0.584187 0.353739 0.023 Uiso 1 1 calc R . . . .
C9 C 0.5546(3) 0.2944(4) 0.4381(2) 0.0182(8) Uani 1 1 d . . . . .
H9 H 0.525937 0.309464 0.487952 0.022 Uiso 1 1 calc R . . . .
C10 C 0.5350(3) 0.6806(4) 0.5285(2) 0.0164(8) Uani 1 1 d . . . . .
H10 H 0.495012 0.746236 0.494595 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4422(3) 0.2685(4) 0.6624(2) 0.0163(7) Uani 1 1 d . . . . .
C12 C 0.3830(3) 0.1528(4) 0.6158(2) 0.0185(8) Uani 1 1 d . . . . .
C13 C 0.7487(3) 0.8575(4) 0.3512(3) 0.0211(8) Uani 1 1 d . . . . .
H13A H 0.792334 0.821852 0.308588 0.032 Uiso 1 1 calc GR . . . .
H13B H 0.778186 0.818412 0.400882 0.032 Uiso 1 1 calc GR . . . .
H13C H 0.748976 0.968681 0.352283 0.032 Uiso 1 1 calc GR . . . .
C14 C 0.2544(4) 0.0182(5) 0.5563(3) 0.0313(11) Uani 1 1 d . . . . .
H14 H 0.186243 -0.017143 0.538701 0.038 Uiso 1 1 calc R . . . .
C15 C 0.2722(4) 0.1374(5) 0.6033(3) 0.0254(9) Uani 1 1 d . . . . .
H15 H 0.219193 0.200696 0.624423 0.031 Uiso 1 1 calc R . . . .
C16 C 0.7406(3) 0.4036(5) 0.5785(3) 0.0200(8) Uani 1 1 d . . . . .
H16A H 0.712341 0.301655 0.587375 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.789897 0.431394 0.621709 0.030 Uiso 1 1 calc GR . . . .
H16C H 0.778511 0.404872 0.529534 0.030 Uiso 1 1 calc GR . . . .
C17 C 0.4279(4) 0.0377(5) 0.5741(3) 0.0251(9) Uani 1 1 d . . . . .
H17 H 0.502350 0.020246 0.571771 0.030 Uiso 1 1 calc R . . . .
B1 B 0.6558(4) 0.5569(4) 0.4240(3) 0.0147(9) Uani 1 1 d . . . . .
H1 H 0.735061 0.566643 0.422024 0.018 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cu1 O1 2.004(3) . ?
Cu1 O2 2.438(3) . ?
Cu1 N2 1.973(4) . ?
Cu1 N3 1.975(3) 4_455 ?
Cu1 N4 1.979(3) 4_465 ?
Cu1 C11 2.524(4) . ?
O1 C11 1.274(5) . ?
O2 C11 1.250(5) . ?
O3 C14 1.414(7) . ?
O3 C17 1.342(6) . ?
N1 C1 1.357(5) . ?
N1 C10 1.379(5) . ?
N1 B1 1.551(6) . ?
N2 C1 1.334(5) . ?
N2 C4 1.390(5) . ?
N3 C2 1.382(5) . ?
N3 C7 1.343(5) . ?
N4 C3 1.377(5) . ?
N4 C5 1.338(5) . ?
N5 C5 1.358(5) . ?
N5 C8 1.389(5) . ?
N5 B1 1.547(5) . ?
N6 C7 1.351(5) . ?
N6 C9 1.385(5) . ?
N6 B1 1.558(5) . ?
C1 C16 1.492(5) . ?
C2 H2 0.9500 . ?
C2 C9 1.350(5) . ?
C3 H3 0.9500 . ?
C3 C8 1.356(5) . ?
C4 H4 0.9500 . ?
C4 C10 1.351(6) . ?
C5 C13 1.481(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C7 1.490(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.479(5) . ?
C12 C15 1.408(6) . ?
C12 C17 1.373(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C15 1.337(7) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
B1 H1 1.0000 . ?

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
O1 Cu1 O2 59.09(10) . . ?
O1 Cu1 C11 29.98(12) . . ?
O2 Cu1 C11 29.11(11) . . ?
N2 Cu1 O1 87.71(12) . . ?
N2 Cu1 O2 93.38(12) . . ?
N2 Cu1 N3 165.83(14) . 4_455 ?
N2 Cu1 N4 93.10(14) . 4_465 ?
N2 Cu1 C11 90.63(13) . . ?
N3 Cu1 O1 90.37(13) 4_455 . ?
N3 Cu1 O2 97.67(12) 4_455 . ?
N3 Cu1 N4 92.71(13) 4_455 4_465 ?
N3 Cu1 C11 94.71(13) 4_455 . ?
N4 Cu1 O1 163.47(12) 4_465 . ?
N4 Cu1 O2 104.39(12) 4_465 . ?
N4 Cu1 C11 133.50(13) 4_465 . ?
C11 O1 Cu1 98.2(2) . . ?
C11 O2 Cu1 79.3(2) . . ?
C17 O3 C14 105.5(4) . . ?
C1 N1 C10 106.0(3) . . ?
C1 N1 B1 126.4(3) . . ?
C10 N1 B1 127.3(3) . . ?
C1 N2 Cu1 126.7(3) . . ?
C1 N2 C4 105.7(4) . . ?
C4 N2 Cu1 123.7(3) . . ?
C2 N3 Cu1 123.9(3) . 4_454 ?
C7 N3 Cu1 129.1(3) . 4_454 ?
C7 N3 C2 105.8(3) . . ?
C3 N4 Cu1 124.3(3) . 4_464 ?
C5 N4 Cu1 129.2(3) . 4_464 ?
C5 N4 C3 106.4(3) . . ?
C5 N5 C8 106.4(3) . . ?
C5 N5 B1 128.3(3) . . ?
C8 N5 B1 125.3(3) . . ?
C7 N6 C9 106.8(3) . . ?
C7 N6 B1 124.5(3) . . ?
C9 N6 B1 128.7(3) . . ?
N1 C1 C16 124.6(4) . . ?
N2 C1 N1 111.5(3) . . ?
N2 C1 C16 123.9(4) . . ?
N3 C2 H2 125.3 . . ?
C9 C2 N3 109.4(3) . . ?
C9 C2 H2 125.3 . . ?
N4 C3 H3 125.4 . . ?
C8 C3 N4 109.1(3) . . ?
C8 C3 H3 125.4 . . ?
N2 C4 H4 125.6 . . ?
C10 C4 N2 108.8(4) . . ?
C10 C4 H4 125.6 . . ?
N4 C5 N5 110.8(3) . . ?
N4 C5 C13 124.1(3) . . ?
N5 C5 C13 125.1(4) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
N3 C7 N6 110.9(3) . . ?
N3 C7 C6 125.4(3) . . ?
N6 C7 C6 123.8(3) . . ?
N5 C8 H8 126.4 . . ?
C3 C8 N5 107.3(3) . . ?
C3 C8 H8 126.4 . . ?
N6 C9 H9 126.4 . . ?
C2 C9 N6 107.2(3) . . ?
C2 C9 H9 126.4 . . ?
N1 C10 H10 126.0 . . ?
C4 C10 N1 108.0(3) . . ?
C4 C10 H10 126.0 . . ?
O1 C11 Cu1 51.81(19) . . ?
O1 C11 C12 116.6(3) . . ?
O2 C11 Cu1 71.6(2) . . ?
O2 C11 O1 123.4(4) . . ?
O2 C11 C12 120.0(3) . . ?
C12 C11 Cu1 168.3(3) . . ?
C15 C12 C11 128.6(4) . . ?
C17 C12 C11 125.7(4) . . ?
C17 C12 C15 105.7(4) . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 H14 125.3 . . ?
C15 C14 O3 109.3(4) . . ?
C15 C14 H14 125.3 . . ?
C12 C15 H15 126.0 . . ?
C14 C15 C12 108.1(4) . . ?
C14 C15 H15 126.0 . . ?
C1 C16 H16A 109.5 . . ?
C1 C16 H16B 109.5 . . ?
C1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C12 111.4(4) . . ?
O3 C17 H17 124.3 . . ?
C12 C17 H17 124.3 . . ?
N1 B1 N6 108.2(3) . . ?
N1 B1 H1 111.2 . . ?
N5 B1 N1 107.7(3) . . ?
N5 B1 N6 107.2(3) . . ?
N5 B1 H1 111.2 . . ?
N6 B1 H1 111.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C11 O2 -0.2(4) . . . . ?
Cu1 O1 C11 C12 178.9(3) . . . . ?
Cu1 O2 C11 O1 0.1(3) . . . . ?
Cu1 O2 C11 C12 -178.9(3) . . . . ?
Cu1 N2 C1 N1 157.2(3) . . . . ?
Cu1 N2 C1 C16 -23.3(5) . . . . ?
Cu1 N2 C4 C10 -158.1(3) . . . . ?
Cu1 N3 C2 C9 -168.1(3) 4_454 . . . ?
Cu1 N3 C7 N6 167.6(3) 4_454 . . . ?
Cu1 N3 C7 C6 -10.7(6) 4_454 . . . ?
Cu1 N4 C3 C8 175.1(3) 4_464 . . . ?
Cu1 N4 C5 N5 -174.7(3) 4_464 . . . ?
Cu1 N4 C5 C13 4.5(6) 4_464 . . . ?
Cu1 C11 C12 C15 -175.5(11) . . . . ?
Cu1 C11 C12 C17 3.2(16) . . . . ?
O1 C11 C12 C15 -179.8(4) . . . . ?
O1 C11 C12 C17 -1.1(6) . . . . ?
O2 C11 C12 C15 -0.7(6) . . . . ?
O2 C11 C12 C17 178.0(4) . . . . ?
O3 C14 C15 C12 0.0(5) . . . . ?
N2 C4 C10 N1 -0.5(4) . . . . ?
N3 C2 C9 N6 -0.4(5) . . . . ?
N4 C3 C8 N5 0.2(5) . . . . ?
C1 N1 C10 C4 -0.1(4) . . . . ?
C1 N1 B1 N5 -177.3(3) . . . . ?
C1 N1 B1 N6 67.1(5) . . . . ?
C1 N2 C4 C10 0.8(4) . . . . ?
C2 N3 C7 N6 0.0(4) . . . . ?
C2 N3 C7 C6 -178.3(4) . . . . ?
C3 N4 C5 N5 0.7(4) . . . . ?
C3 N4 C5 C13 179.9(4) . . . . ?
C4 N2 C1 N1 -0.9(4) . . . . ?
C4 N2 C1 C16 178.6(4) . . . . ?
C5 N4 C3 C8 -0.5(5) . . . . ?
C5 N5 C8 C3 0.2(4) . . . . ?
C5 N5 B1 N1 101.0(4) . . . . ?
C5 N5 B1 N6 -142.8(4) . . . . ?
C7 N3 C2 C9 0.3(4) . . . . ?
C7 N6 C9 C2 0.4(4) . . . . ?
C7 N6 B1 N1 -178.0(3) . . . . ?
C7 N6 B1 N5 66.1(5) . . . . ?
C8 N5 C5 N4 -0.5(4) . . . . ?
C8 N5 C5 C13 -179.7(4) . . . . ?
C8 N5 B1 N1 -75.2(4) . . . . ?
C8 N5 B1 N6 41.0(5) . . . . ?
C9 N6 C7 N3 -0.2(4) . . . . ?
C9 N6 C7 C6 178.0(4) . . . . ?
C9 N6 B1 N1 4.4(6) . . . . ?
C9 N6 B1 N5 -111.5(4) . . . . ?
C10 N1 C1 N2 0.6(4) . . . . ?
C10 N1 C1 C16 -178.9(4) . . . . ?
C10 N1 B1 N5 9.6(5) . . . . ?
C10 N1 B1 N6 -106.0(4) . . . . ?
C11 C12 C15 C14 179.0(4) . . . . ?
C11 C12 C17 O3 -179.0(4) . . . . ?
C14 O3 C17 C12 0.1(5) . . . . ?
C15 C12 C17 O3 -0.1(5) . . . . ?
C17 O3 C14 C15 0.0(5) . . . . ?
C17 C12 C15 C14 0.1(5) . . . . ?
B1 N1 C1 N2 -173.7(3) . . . . ?
B1 N1 C1 C16 6.8(6) . . . . ?
B1 N1 C10 C4 174.2(3) . . . . ?
B1 N5 C5 N4 -177.3(3) . . . . ?
B1 N5 C5 C13 3.5(6) . . . . ?
B1 N5 C8 C3 177.1(4) . . . . ?
B1 N6 C7 N3 -178.2(3) . . . . ?
B1 N6 C7 C6 0.1(6) . . . . ?
B1 N6 C9 C2 178.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.599
_oxdiff_exptl_absorpt_empirical_full_min 0.403
