# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1-L
_database_code_depnum_ccdc_archive 'CCDC 1985392'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xuan Xu'
;School of chemistry and chemical engineering, Zunyi Normal College
China
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Cu N3 O5, C5 H11 N O, H2 O'
_chemical_formula_sum            'C28 H32 Cu N4 O7'
_chemical_formula_weight         600.11
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCu
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4610(6)
_cell_length_b                   26.3464(13)
_cell_length_c                   11.1125(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2769.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6732
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.8240
_cell_measurement_theta_min      4.0100
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.729
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22502
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.198
_diffrn_reflns_theta_min         3.658
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -27.00  30.00   0.50  153.11    --   -0.00 -82.00  60.00  114
  2  ω    -51.00  -7.00   0.50  153.11    --   -0.00 -82.00 -90.00   88
  3  ω    -76.00 -49.00   0.50  153.11    --   -0.00 -77.00 -60.00   54
  4  ω    -29.00  -3.00   0.50  153.11    --   -0.00 -77.00 -60.00   52
  5  ω    -15.00  22.50   0.50  153.11    --   -0.00  37.00 -71.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0432616000
_diffrn_orient_matrix_UB_12      0.0190176000
_diffrn_orient_matrix_UB_13      -0.0261801000
_diffrn_orient_matrix_UB_21      0.0611497000
_diffrn_orient_matrix_UB_22      0.0141888000
_diffrn_orient_matrix_UB_23      -0.0151891000
_diffrn_orient_matrix_UB_31      0.0035361000
_diffrn_orient_matrix_UB_32      -0.0127208000
_diffrn_orient_matrix_UB_33      -0.0561703000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                6351
_reflns_number_total             7267
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 2404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         7267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C25(H25A,H25B), C27(H27A,H27B)
2.d Aromatic/amide H refined with riding coordinates:
 C18(H18), C20(H20), C23(H23), C22(H22), C9(H9), C14(H14), C21(H21), C8(H8),
 C15(H15), C11(H11), C17(H17), C12(H12), C28(H28)
2.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.11610(3) 0.42982(2) 0.65711(3) 0.02275(9) Uani 1 1 d . . . . .
O1 O 0.2618(2) 0.48204(6) 0.6506(2) 0.0281(4) Uani 1 1 d . . . . .
O4 O 0.4420(2) 0.85696(6) 0.3457(2) 0.0285(4) Uani 1 1 d . . . . .
O2 O 0.1289(2) 0.55173(8) 0.6607(2) 0.0357(4) Uani 1 1 d . . . . .
N2 N 0.1116(2) 0.43269(7) 0.8395(2) 0.0265(4) Uani 1 1 d . . . . .
N3 N 0.1118(3) 0.43161(9) 1.4751(2) 0.0282(4) Uani 1 1 d . . . . .
O3 O 0.3755(4) 0.58365(8) 0.3981(3) 0.0617(8) Uani 1 1 d . . . . .
O5 O 0.2097(2) 0.85139(9) 0.3425(4) 0.0582(8) Uani 1 1 d . . . . .
N1 N 0.3581(3) 0.61063(8) 0.5883(3) 0.0333(6) Uani 1 1 d . . . . .
C10 C 0.3389(3) 0.77544(9) 0.3725(3) 0.0280(6) Uani 1 1 d . . . . .
C19 C 0.1052(3) 0.43439(11) 1.2235(3) 0.0320(6) Uani 1 1 d . . . . .
C1 C 0.2418(3) 0.52986(9) 0.6501(3) 0.0224(5) Uani 1 1 d . . . . .
C13 C 0.3262(3) 0.83201(9) 0.3511(3) 0.0285(5) Uani 1 1 d . . . . .
C18 C 0.0175(4) 0.40542(13) 0.9012(3) 0.0369(7) Uani 1 1 d . . . . .
H18 H -0.045029 0.384976 0.858575 0.044 Uiso 1 1 calc R . . . .
C6 C 0.3641(3) 0.61851(10) 0.4711(3) 0.0345(7) Uani 1 1 d . . . . .
C20 C 0.2312(4) 0.43849(17) 1.2876(3) 0.0446(9) Uani 1 1 d . . . . .
H20 H 0.316238 0.442417 1.246588 0.053 Uiso 1 1 calc R . . . .
C2 C 0.3798(3) 0.56020(8) 0.6402(3) 0.0320(6) Uani 1 1 d . . . . .
H2 H 0.448900 0.541262 0.592267 0.038 Uiso 1 1 calc R . . . .
C23 C -0.0183(3) 0.42857(15) 1.2909(3) 0.0353(6) Uani 1 1 d . . . . .
H23 H -0.105262 0.425551 1.252603 0.042 Uiso 1 1 calc R . . . .
C7 C 0.3542(3) 0.67300(10) 0.4306(3) 0.0332(7) Uani 1 1 d . . . . .
C22 C -0.0103(3) 0.42734(15) 1.4141(3) 0.0354(7) Uani 1 1 d . . . . .
H22 H -0.093554 0.423353 1.457569 0.042 Uiso 1 1 calc R . . . .
C3 C 0.4414(4) 0.57280(14) 0.7624(4) 0.0483(9) Uani 1 1 d . . . . .
H3A H 0.420345 0.546232 0.820084 0.058 Uiso 1 1 calc R . . . .
H3B H 0.543136 0.576945 0.757348 0.058 Uiso 1 1 calc R . . . .
C9 C 0.2176(4) 0.74656(12) 0.3790(4) 0.0480(10) Uani 1 1 d . . . . .
H9 H 0.130168 0.761315 0.363665 0.058 Uiso 1 1 calc R . . . .
C14 C 0.2009(4) 0.46172(14) 0.9032(3) 0.0445(8) Uani 1 1 d . . . . .
H14 H 0.266317 0.481397 0.861689 0.053 Uiso 1 1 calc R . . . .
C16 C 0.1043(3) 0.43507(11) 1.0908(3) 0.0297(6) Uani 1 1 d . . . . .
C21 C 0.2303(4) 0.43677(17) 1.4109(3) 0.0422(9) Uani 1 1 d . . . . .
H21 H 0.315930 0.439298 1.451604 0.051 Uiso 1 1 calc R . . . .
C8 C 0.2262(4) 0.69499(12) 0.4086(5) 0.0532(11) Uani 1 1 d . . . . .
H8 H 0.144230 0.675621 0.413361 0.064 Uiso 1 1 calc R . . . .
C15 C 0.2003(4) 0.46380(15) 1.0268(3) 0.0462(9) Uani 1 1 d . . . . .
H15 H 0.264348 0.484481 1.067077 0.055 Uiso 1 1 calc R . . . .
C11 C 0.4679(3) 0.75273(11) 0.3901(4) 0.0430(8) Uani 1 1 d . . . . .
H11 H 0.550361 0.771650 0.382244 0.052 Uiso 1 1 calc R . . . .
C17 C 0.0085(4) 0.40602(14) 1.0245(3) 0.0394(7) Uani 1 1 d . . . . .
H17 H -0.060913 0.387228 1.063543 0.047 Uiso 1 1 calc R . . . .
C4 C 0.3719(5) 0.62150(15) 0.7977(4) 0.0530(9) Uani 1 1 d . . . . .
H4A H 0.432728 0.640931 0.850743 0.064 Uiso 1 1 calc R . . . .
H4B H 0.283269 0.614946 0.838785 0.064 Uiso 1 1 calc R . . . .
N4 N 0.7415(5) 0.70724(19) 0.0440(5) 0.0780(12) Uani 1 1 d . . . . .
C12 C 0.4755(4) 0.70128(12) 0.4199(4) 0.0517(11) Uani 1 1 d . . . . .
H12 H 0.563082 0.686127 0.432433 0.062 Uiso 1 1 calc R . . . .
C5 C 0.3463(4) 0.64997(12) 0.6817(4) 0.0483(9) Uani 1 1 d . . . . .
H5A H 0.253105 0.665316 0.681144 0.058 Uiso 1 1 calc R . . . .
H5B H 0.416689 0.676288 0.670134 0.058 Uiso 1 1 calc R . . . .
O1W O 0.3698(7) 0.5735(3) 0.1446(6) 0.150(3) Uani 1 1 d . . . . .
H1WA H 0.378227 0.586721 0.213947 0.225 Uiso 1 1 d G . . . .
H1WB H 0.444686 0.582058 0.107627 0.225 Uiso 1 1 d G . . . .
O6 O 0.5903(5) 0.6406(2) 0.0606(6) 0.1226(18) Uani 1 1 d . . . . .
C28 C 0.6697(6) 0.6669(3) 0.0016(6) 0.0852(17) Uani 1 1 d . . . . .
H28 H 0.681826 0.658492 -0.079026 0.102 Uiso 1 1 calc R . . . .
C25 C 0.8324(7) 0.7364(3) -0.0341(6) 0.0921(18) Uani 1 1 d . . . . .
H25A H 0.854222 0.716450 -0.105162 0.111 Uiso 1 1 calc R . . . .
H25B H 0.920437 0.743455 0.007297 0.111 Uiso 1 1 calc R . . . .
C26 C 0.8417(7) 0.7101(3) 0.2460(6) 0.102(2) Uani 1 1 d . . . . .
H26A H 0.928572 0.721779 0.211052 0.153 Uiso 1 1 calc GR . . . .
H26B H 0.845547 0.673886 0.255902 0.153 Uiso 1 1 calc GR . . . .
H26C H 0.828354 0.725866 0.322979 0.153 Uiso 1 1 calc GR . . . .
C27 C 0.7252(7) 0.7231(3) 0.1677(6) 0.0952(18) Uani 1 1 d . . . . .
H27A H 0.712579 0.759585 0.169394 0.114 Uiso 1 1 calc R . . . .
H27B H 0.639747 0.707812 0.199625 0.114 Uiso 1 1 calc R . . . .
C24 C 0.7642(10) 0.7863(3) -0.0724(8) 0.121(3) Uani 1 1 d . . . . .
H24A H 0.829394 0.805205 -0.121113 0.182 Uiso 1 1 calc GR . . . .
H24B H 0.740139 0.805710 -0.002262 0.182 Uiso 1 1 calc GR . . . .
H24C H 0.680186 0.779361 -0.117993 0.182 Uiso 1 1 calc GR . . . .


_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 1.9489(18) . ?
Cu1 O4 1.9972(17) 3_546 ?
Cu1 O2 2.3689(19) 2_565 ?
Cu1 N2 2.029(2) . ?
Cu1 N3 2.023(2) 1_554 ?
O1 C1 1.274(3) . ?
O4 C13 1.279(3) . ?
O2 C1 1.219(3) . ?
N2 C18 1.333(4) . ?
N2 C14 1.341(4) . ?
N3 C22 1.344(4) . ?
N3 C21 1.336(4) . ?
O3 C6 1.230(4) . ?
O5 C13 1.218(4) . ?
N1 C6 1.320(4) . ?
N1 C2 1.463(3) . ?
N1 C5 1.471(4) . ?
C10 C13 1.514(3) . ?
C10 C9 1.379(4) . ?
C10 C11 1.373(4) . ?
C19 C20 1.393(5) . ?
C19 C23 1.396(4) . ?
C19 C16 1.475(4) . ?
C1 C2 1.534(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.373(5) . ?
C6 C7 1.508(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.371(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.515(5) . ?
C23 H23 0.9300 . ?
C23 C22 1.371(4) . ?
C7 C8 1.364(5) . ?
C7 C12 1.374(4) . ?
C22 H22 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.495(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.400(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(5) . ?
C16 C15 1.380(4) . ?
C16 C17 1.397(4) . ?
C21 H21 0.9300 . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.397(4) . ?
C17 H17 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.511(6) . ?
N4 C28 1.347(8) . ?
N4 C25 1.442(8) . ?
N4 C27 1.445(8) . ?
C12 H12 0.9300 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O1W H1WA 0.8498 . ?
O1W H1WB 0.8499 . ?
O6 C28 1.214(8) . ?
C28 H28 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C24 1.526(10) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 C27 1.445(9) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 O4 150.78(8) . 3_546 ?
O1 Cu1 O2 123.23(7) . 2_565 ?
O1 Cu1 N2 91.48(9) . . ?
O1 Cu1 N3 87.74(10) . 1_554 ?
O4 Cu1 O2 85.87(7) 3_546 2_565 ?
O4 Cu1 N2 92.62(9) 3_546 . ?
O4 Cu1 N3 90.06(10) 3_546 1_554 ?
N2 Cu1 O2 87.42(9) . 2_565 ?
N3 Cu1 O2 89.56(10) 1_554 2_565 ?
N3 Cu1 N2 175.80(9) 1_554 . ?
C1 O1 Cu1 126.39(17) . . ?
C13 O4 Cu1 105.00(15) . 3_556 ?
C1 O2 Cu1 162.27(19) . 2_565 ?
C18 N2 Cu1 120.50(19) . . ?
C18 N2 C14 117.2(3) . . ?
C14 N2 Cu1 122.3(2) . . ?
C22 N3 Cu1 121.3(2) . 1_556 ?
C21 N3 Cu1 121.3(2) . 1_556 ?
C21 N3 C22 117.4(3) . . ?
C6 N1 C2 121.7(2) . . ?
C6 N1 C5 126.1(2) . . ?
C2 N1 C5 111.8(3) . . ?
C9 C10 C13 119.0(3) . . ?
C11 C10 C13 121.5(2) . . ?
C11 C10 C9 119.4(2) . . ?
C20 C19 C23 116.8(3) . . ?
C20 C19 C16 121.0(3) . . ?
C23 C19 C16 122.2(3) . . ?
O1 C1 C2 112.9(2) . . ?
O2 C1 O1 126.7(2) . . ?
O2 C1 C2 120.4(2) . . ?
O4 C13 C10 116.4(2) . . ?
O5 C13 O4 123.8(2) . . ?
O5 C13 C10 119.8(3) . . ?
N2 C18 H18 118.4 . . ?
N2 C18 C17 123.3(3) . . ?
C17 C18 H18 118.4 . . ?
O3 C6 N1 122.5(3) . . ?
O3 C6 C7 121.3(3) . . ?
N1 C6 C7 116.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(3) . . ?
C21 C20 H20 119.9 . . ?
N1 C2 C1 112.5(2) . . ?
N1 C2 H2 110.0 . . ?
N1 C2 C3 102.0(2) . . ?
C1 C2 H2 110.0 . . ?
C3 C2 C1 112.2(3) . . ?
C3 C2 H2 110.0 . . ?
C19 C23 H23 120.3 . . ?
C22 C23 C19 119.5(3) . . ?
C22 C23 H23 120.3 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 C12 119.7(3) . . ?
C12 C7 C6 119.4(3) . . ?
N3 C22 C23 123.3(3) . . ?
N3 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 C2 104.7(3) . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
N2 C14 H14 118.4 . . ?
N2 C14 C15 123.2(3) . . ?
C15 C14 H14 118.4 . . ?
C15 C16 C19 121.2(3) . . ?
C15 C16 C17 117.1(3) . . ?
C17 C16 C19 121.6(3) . . ?
N3 C21 C20 122.8(3) . . ?
N3 C21 H21 118.6 . . ?
C20 C21 H21 118.6 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C3 C4 C5 105.8(3) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C28 N4 C25 120.7(6) . . ?
C28 N4 C27 120.4(6) . . ?
C25 N4 C27 118.9(5) . . ?
C7 C12 C11 120.2(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N1 C5 C4 103.9(3) . . ?
N1 C5 H5A 111.0 . . ?
N1 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
H1WA O1W H1WB 104.5 . . ?
N4 C28 H28 117.5 . . ?
O6 C28 N4 125.0(7) . . ?
O6 C28 H28 117.5 . . ?
N4 C25 H25A 109.2 . . ?
N4 C25 H25B 109.2 . . ?
N4 C25 C24 112.0(6) . . ?
H25A C25 H25B 107.9 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
N4 C27 H27A 108.5 . . ?
N4 C27 H27B 108.5 . . ?
C26 C27 N4 115.0(5) . . ?
C26 C27 H27A 108.5 . . ?
C26 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.470
_oxdiff_exptl_absorpt_empirical_full_min 0.394
####################################################################### 
# 
# 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_1-D
_database_code_depnum_ccdc_archive 'CCDC 1985393'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xuan Xu'
;School of chemistry and chemical engineering, Zunyi Normal College
China
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Cu N3 O5, C5 H11 N O, H2 O'
_chemical_formula_sum            'C28 H32 Cu N4 O7'
_chemical_formula_weight         600.11
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCu
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.4529(6)
_cell_length_b                   26.3871(10)
_cell_length_c                   11.1375(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2778.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10108
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0630
_cell_measurement_theta_min      4.1820
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36655
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.236
_diffrn_reflns_theta_min         3.766
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00 -36.00   0.50   63.66    --   -0.00 -34.00 115.00   50
  2  ω    -76.00  28.00   0.50   63.66    --   -0.00 -77.00 -60.00  208
  3  ω    -15.00  60.00   0.50   63.66    --   -0.00  38.00   0.00  150
  4  ω    -40.00 -15.00   0.50   63.66    --   -0.00 -82.00-120.00   50
  5  ω     46.00  71.00   0.50   63.66    --   -0.00  57.00-180.00   50
  6  ω     22.00  52.00   0.50   63.66    --   -0.00  57.00 150.00   60
  7  ω     36.00  61.00   0.50   63.66    --   -0.00  57.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0562808000
_diffrn_orient_matrix_UB_12      -0.0135607000
_diffrn_orient_matrix_UB_13      0.0272551000
_diffrn_orient_matrix_UB_21      0.0382139000
_diffrn_orient_matrix_UB_22      0.0229342000
_diffrn_orient_matrix_UB_23      0.0070811000
_diffrn_orient_matrix_UB_31      -0.0315676000
_diffrn_orient_matrix_UB_32      0.0036264000
_diffrn_orient_matrix_UB_33      0.0571410000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                6714
_reflns_number_total             7626
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 2592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         7626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.031
_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)+(0.0456P)²+0.4779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B), C27(H27A,H27B), C25(H25A,H25B)
2.d Aromatic/amide H refined with riding coordinates:
 C22(H22), C17(H17), C18(H18), C9(H9), C15(H15), C14(H14), C21(H21), C11(H11),
 C23(H23), C20(H20), C8(H8), C12(H12), C24(H24)
2.e Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.11629(3) 0.57013(2) 0.65730(3) 0.02273(8) Uani 1 1 d . . . . .
O1 O 0.2623(2) 0.51786(6) 0.65080(18) 0.0280(4) Uani 1 1 d . . . . .
O5 O 0.4420(2) 0.14303(6) 0.34559(19) 0.0287(4) Uani 1 1 d . . . . .
O2 O 0.1286(2) 0.44825(7) 0.6611(2) 0.0356(4) Uani 1 1 d . . . . .
N3 N 0.1113(2) 0.56716(7) -0.16014(18) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.1115(3) 0.56825(9) 0.47501(18) 0.0287(4) Uani 1 1 d . . . . .
O3 O 0.3752(4) 0.41632(8) 0.3981(2) 0.0606(7) Uani 1 1 d . . . . .
O4 O 0.2096(2) 0.14866(8) 0.3427(3) 0.0594(7) Uani 1 1 d . . . . .
N1 N 0.3576(3) 0.38935(8) 0.5886(2) 0.0333(6) Uani 1 1 d . . . . .
C10 C 0.3393(3) 0.22459(9) 0.3724(2) 0.0273(5) Uani 1 1 d . . . . .
C22 C 0.0177(3) 0.59472(12) -0.0992(3) 0.0361(7) Uani 1 1 d . . . . .
H22 H -0.044636 0.615277 -0.141604 0.043 Uiso 1 1 calc R . . . .
C1 C 0.2422(3) 0.47015(9) 0.6500(2) 0.0231(4) Uani 1 1 d . . . . .
C16 C 0.1058(4) 0.56555(11) 0.2243(2) 0.0324(6) Uani 1 1 d . . . . .
C13 C 0.3262(3) 0.16795(9) 0.3509(3) 0.0286(5) Uani 1 1 d . . . . .
C6 C 0.3636(3) 0.38142(9) 0.4713(3) 0.0341(6) Uani 1 1 d . . . . .
C17 C -0.0174(3) 0.57141(15) 0.2906(2) 0.0355(6) Uani 1 1 d . . . . .
H17 H -0.104333 0.574392 0.252098 0.043 Uiso 1 1 calc R . . . .
C18 C -0.0094(3) 0.57275(14) 0.4145(2) 0.0357(6) Uani 1 1 d . . . . .
H18 H -0.092710 0.577001 0.457856 0.043 Uiso 1 1 calc R . . . .
C2 C 0.3802(3) 0.43988(8) 0.6402(3) 0.0321(6) Uani 1 1 d . . . . .
H2 H 0.449535 0.458681 0.592314 0.039 Uiso 1 1 calc R . . . .
C7 C 0.3545(3) 0.32678(9) 0.4310(3) 0.0330(6) Uani 1 1 d . . . . .
C3 C 0.4419(4) 0.42709(13) 0.7626(3) 0.0474(8) Uani 1 1 d . . . . .
H3A H 0.543610 0.422745 0.757715 0.057 Uiso 1 1 calc R . . . .
H3B H 0.421061 0.453610 0.820291 0.057 Uiso 1 1 calc R . . . .
C9 C 0.2182(4) 0.25349(12) 0.3789(4) 0.0500(10) Uani 1 1 d . . . . .
H9 H 0.130717 0.238717 0.363599 0.060 Uiso 1 1 calc R . . . .
C15 C 0.2315(4) 0.56117(16) 0.2873(3) 0.0444(9) Uani 1 1 d . . . . .
H15 H 0.316553 0.557039 0.246486 0.053 Uiso 1 1 calc R . . . .
C14 C 0.2299(4) 0.56297(16) 0.4110(3) 0.0420(8) Uani 1 1 d . . . . .
H14 H 0.315394 0.560365 0.451763 0.050 Uiso 1 1 calc R . . . .
C21 C 0.2005(4) 0.53807(13) -0.0971(3) 0.0438(8) Uani 1 1 d . . . . .
H21 H 0.265924 0.518484 -0.138725 0.053 Uiso 1 1 calc R . . . .
C11 C 0.4679(3) 0.24725(11) 0.3906(3) 0.0431(8) Uani 1 1 d . . . . .
H11 H 0.550454 0.228333 0.383546 0.052 Uiso 1 1 calc R . . . .
C19 C 0.1042(3) 0.56478(10) 0.0911(2) 0.0298(5) Uani 1 1 d . . . . .
C23 C 0.0097(4) 0.59396(13) 0.0249(3) 0.0391(7) Uani 1 1 d . . . . .
H23 H -0.058981 0.612999 0.064095 0.047 Uiso 1 1 calc R . . . .
C20 C 0.2001(4) 0.53570(14) 0.0269(3) 0.0459(8) Uani 1 1 d . . . . .
H20 H 0.263695 0.514772 0.066956 0.055 Uiso 1 1 calc R . . . .
C8 C 0.2261(4) 0.30502(12) 0.4084(4) 0.0532(10) Uani 1 1 d . . . . .
H8 H 0.144065 0.324396 0.412546 0.064 Uiso 1 1 calc R . . . .
C12 C 0.4754(4) 0.29852(11) 0.4197(4) 0.0512(10) Uani 1 1 d . . . . .
H12 H 0.563138 0.313686 0.431578 0.061 Uiso 1 1 calc R . . . .
N4 N 0.7412(5) 0.29281(17) 0.0438(4) 0.0767(11) Uani 1 1 d . . . . .
C5 C 0.3467(4) 0.34993(11) 0.6817(3) 0.0485(9) Uani 1 1 d . . . . .
H5A H 0.418057 0.323948 0.670254 0.058 Uiso 1 1 calc R . . . .
H5B H 0.253964 0.334232 0.680847 0.058 Uiso 1 1 calc R . . . .
C4 C 0.3710(5) 0.37834(15) 0.7976(3) 0.0534(9) Uani 1 1 d . . . . .
H4A H 0.281836 0.385004 0.837720 0.064 Uiso 1 1 calc R . . . .
H4B H 0.431023 0.358887 0.851155 0.064 Uiso 1 1 calc R . . . .
O6 O 0.5896(5) 0.35943(19) 0.0603(5) 0.1191(16) Uani 1 1 d . . . . .
O1W O 0.3679(7) 0.4260(3) 0.1443(5) 0.144(2) Uani 1 1 d . . . . .
H1WA H 0.369122 0.412843 0.213949 0.217 Uiso 1 1 d G . . . .
H1WB H 0.444168 0.415835 0.111698 0.217 Uiso 1 1 d G . . . .
C27 C 0.8324(6) 0.2635(3) -0.0343(5) 0.0911(17) Uani 1 1 d . . . . .
H27A H 0.920906 0.256743 0.006688 0.109 Uiso 1 1 calc R . . . .
H27B H 0.853362 0.283139 -0.105742 0.109 Uiso 1 1 calc R . . . .
C24 C 0.6691(6) 0.3329(2) 0.0018(6) 0.0833(15) Uani 1 1 d . . . . .
H24 H 0.680979 0.341153 -0.078825 0.100 Uiso 1 1 calc R . . . .
C26 C 0.8427(7) 0.2899(2) 0.2462(6) 0.101(2) Uani 1 1 d . . . . .
H26A H 0.930078 0.280734 0.208075 0.152 Uiso 1 1 calc GR . . . .
H26B H 0.833599 0.271767 0.320572 0.152 Uiso 1 1 calc GR . . . .
H26C H 0.842001 0.325671 0.261825 0.152 Uiso 1 1 calc GR . . . .
C25 C 0.7247(7) 0.2770(3) 0.1676(5) 0.0933(17) Uani 1 1 d . . . . .
H25A H 0.711627 0.240527 0.169248 0.112 Uiso 1 1 calc R . . . .
H25B H 0.639419 0.292335 0.199523 0.112 Uiso 1 1 calc R . . . .
C28 C 0.7645(10) 0.2134(3) -0.0709(7) 0.120(3) Uani 1 1 d . . . . .
H28A H 0.831173 0.193736 -0.116161 0.181 Uiso 1 1 calc GR . . . .
H28B H 0.682481 0.220012 -0.119322 0.181 Uiso 1 1 calc GR . . . .
H28C H 0.737037 0.195018 -0.000318 0.181 Uiso 1 1 calc GR . . . .


_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 1.9523(17) . ?
Cu1 O5 2.0014(16) 3_556 ?
Cu1 O2 2.365(2) 2_565 ?
Cu1 N3 2.035(2) 1_556 ?
Cu1 N2 2.031(2) . ?
O1 C1 1.273(3) . ?
O5 C13 1.278(3) . ?
O2 C1 1.226(3) . ?
N3 C22 1.331(4) . ?
N3 C21 1.339(4) . ?
N2 C18 1.332(4) . ?
N2 C14 1.334(4) . ?
O3 C6 1.235(4) . ?
O4 C13 1.218(4) . ?
N1 C6 1.324(4) . ?
N1 C2 1.468(3) . ?
N1 C5 1.473(4) . ?
C10 C13 1.519(3) . ?
C10 C9 1.377(4) . ?
C10 C11 1.370(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(4) . ?
C1 C2 1.533(4) . ?
C16 C17 1.388(4) . ?
C16 C15 1.385(5) . ?
C16 C19 1.483(3) . ?
C6 C7 1.512(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9300 . ?
C2 H2 0.9800 . ?
C2 C3 1.521(4) . ?
C7 C8 1.366(5) . ?
C7 C12 1.371(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.502(5) . ?
C9 H9 0.9300 . ?
C9 C8 1.401(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.378(4) . ?
C14 H14 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.382(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.393(4) . ?
C19 C23 1.391(4) . ?
C19 C20 1.386(4) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C8 H8 0.9300 . ?
C12 H12 0.9300 . ?
N4 C27 1.448(7) . ?
N4 C24 1.344(7) . ?
N4 C25 1.449(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.510(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
O6 C24 1.216(7) . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8502 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.525(9) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 C25 1.458(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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 O5 150.82(8) . 3_556 ?
O1 Cu1 O2 123.19(7) . 2_565 ?
O1 Cu1 N3 91.50(8) . 1_556 ?
O1 Cu1 N2 87.79(9) . . ?
O5 Cu1 O2 85.87(7) 3_556 2_565 ?
O5 Cu1 N3 92.68(8) 3_556 1_556 ?
O5 Cu1 N2 90.07(9) 3_556 . ?
N3 Cu1 O2 87.24(8) 1_556 2_565 ?
N2 Cu1 O2 89.48(9) . 2_565 ?
N2 Cu1 N3 175.56(8) . 1_556 ?
C1 O1 Cu1 126.42(17) . . ?
C13 O5 Cu1 105.04(15) . 3_546 ?
C1 O2 Cu1 162.24(18) . 2_565 ?
C22 N3 Cu1 120.24(18) . 1_554 ?
C22 N3 C21 117.6(2) . . ?
C21 N3 Cu1 122.12(19) . 1_554 ?
C18 N2 Cu1 121.49(19) . . ?
C14 N2 Cu1 121.2(2) . . ?
C14 N2 C18 117.3(2) . . ?
C6 N1 C2 121.6(2) . . ?
C6 N1 C5 125.9(2) . . ?
C2 N1 C5 112.1(2) . . ?
C9 C10 C13 119.0(3) . . ?
C11 C10 C13 121.7(2) . . ?
C11 C10 C9 119.2(2) . . ?
N3 C22 H22 118.7 . . ?
N3 C22 C23 122.5(3) . . ?
C23 C22 H22 118.7 . . ?
O1 C1 C2 112.9(2) . . ?
O2 C1 O1 126.6(2) . . ?
O2 C1 C2 120.5(2) . . ?
C17 C16 C19 121.7(3) . . ?
C15 C16 C17 117.4(2) . . ?
C15 C16 C19 121.0(3) . . ?
O5 C13 C10 116.4(2) . . ?
O4 C13 O5 123.8(2) . . ?
O4 C13 C10 119.8(2) . . ?
O3 C6 N1 122.5(2) . . ?
O3 C6 C7 121.4(3) . . ?
N1 C6 C7 116.1(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H17 120.4 . . ?
N2 C18 C17 123.3(3) . . ?
N2 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
N1 C2 C1 112.2(2) . . ?
N1 C2 H2 110.1 . . ?
N1 C2 C3 101.9(2) . . ?
C1 C2 H2 110.1 . . ?
C3 C2 C1 112.2(2) . . ?
C3 C2 H2 110.1 . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 C12 119.7(3) . . ?
C12 C7 C6 119.9(3) . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 C2 104.6(3) . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 H15 120.2 . . ?
N2 C14 C15 123.2(3) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
N3 C21 H21 118.4 . . ?
N3 C21 C20 123.3(3) . . ?
C20 C21 H21 118.4 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C23 C19 C16 121.9(3) . . ?
C20 C19 C16 121.1(3) . . ?
C20 C19 C23 116.9(3) . . ?
C22 C23 C19 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C19 C23 H23 119.9 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C27 N4 C25 118.8(5) . . ?
C24 N4 C27 120.9(5) . . ?
C24 N4 C25 120.3(5) . . ?
N1 C5 H5A 111.0 . . ?
N1 C5 H5B 111.0 . . ?
N1 C5 C4 103.9(2) . . ?
H5A C5 H5B 109.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
C3 C4 C5 105.7(3) . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.7 . . ?
H1WA O1W H1WB 104.5 . . ?
N4 C27 H27A 109.2 . . ?
N4 C27 H27B 109.2 . . ?
N4 C27 C28 111.9(6) . . ?
H27A C27 H27B 107.9 . . ?
C28 C27 H27A 109.2 . . ?
C28 C27 H27B 109.2 . . ?
N4 C24 H24 117.3 . . ?
O6 C24 N4 125.4(6) . . ?
O6 C24 H24 117.3 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
N4 C25 C26 115.0(5) . . ?
N4 C25 H25A 108.5 . . ?
N4 C25 H25B 108.5 . . ?
C26 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.423
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_2-D
_database_code_depnum_ccdc_archive 'CCDC 1985395'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xuan Xu'
;School of chemistry and chemical engineering, Zunyi Normal College
China
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-01-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Co N3 O5, H2 O, 0.5(O)'
_chemical_formula_sum            'C23 H22 Co N3 O6.50'
_chemical_formula_weight         503.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCo
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.4298(7)
_cell_length_b                   17.5953(9)
_cell_length_c                   23.3164(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4689.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.9170
_cell_measurement_theta_min      3.9420
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25132
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.136
_diffrn_reflns_theta_min         3.671
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  -4.00   0.50  123.80    --   -0.00 -38.00 -90.00   52
  2  ω    -14.00  57.00   0.50  123.80    --   -0.00  19.00-180.00  142
  3  ω     54.00  82.00   0.50  123.80    --   -0.00  38.00   0.00   56
  4  ω    -62.00 -30.00   0.50  123.80    --   -0.00 -77.00  60.00   64
  5  ω    -19.00  48.00   0.50  123.80    --   -0.00  57.00 -30.00  134
  6  ω    -73.00 -48.00   0.50  123.80    --   -0.00 -38.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0336553000
_diffrn_orient_matrix_UB_12      -0.0016012000
_diffrn_orient_matrix_UB_13      0.0255015000
_diffrn_orient_matrix_UB_21      -0.0120968000
_diffrn_orient_matrix_UB_22      0.0389583000
_diffrn_orient_matrix_UB_23      0.0052131000
_diffrn_orient_matrix_UB_31      -0.0507693000
_diffrn_orient_matrix_UB_32      -0.0103049000
_diffrn_orient_matrix_UB_33      0.0157027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.885
_reflns_number_gt                5826
_reflns_number_total             6358
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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         0.247
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 2362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+1.6903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0757
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H3AA(0.7) H3AB(0.7) H3BC(0.3) H3BD(0.3) H5AA(0.7) H5AB(0.7)
 H5BC(0.3) H5BD(0.3) C4A(0.7) H4AA(0.7) H4AB(0.7) C4B(0.3) H4BA(0.3) H4BB(0.3)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C2(H2)
3.c Secondary CH2 refined with riding coordinates:
 C3(H3AA,H3AB), C3(H3BC,H3BD), C5(H5AA,H5AB), C5(H5BC,H5BD), C4A(H4AA,H4AB),
 C4B(H4BA,H4BB)
3.d Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C18(H18), C23(H23), C22(H22), C17(H17), C15(H15),
 C14(H14), C11(H11), C12(H12), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
Co1 Co 0.57559(3) 0.94707(2) 0.57827(2) 0.02036(8) Uani 1 1 d . . . . .
O4 O 0.91004(17) 0.56510(10) 0.16911(7) 0.0353(4) Uani 1 1 d . . . . .
O1 O 0.56641(19) 0.90266(12) 0.49931(8) 0.0426(5) Uani 1 1 d . . . . .
O2 O 0.57238(17) 0.93781(9) 0.40819(7) 0.0325(4) Uani 1 1 d . . . . .
N2 N 0.38674(17) 0.94745(12) 0.57982(9) 0.0273(4) Uani 1 1 d . . . . .
O5 O 0.90529(19) 0.66947(11) 0.11895(8) 0.0400(5) Uani 1 1 d . . . . .
N3 N -0.23636(17) 0.95182(12) 0.57265(9) 0.0265(4) Uani 1 1 d . . . . .
O3 O 0.7877(2) 0.81157(16) 0.40801(11) 0.0542(6) Uani 1 1 d . . . . .
C21 C -0.1738(2) 0.91263(15) 0.53438(12) 0.0307(6) Uani 1 1 d . . . . .
H21 H -0.213580 0.883724 0.507268 0.037 Uiso 1 1 calc R . . . .
C20 C -0.0524(2) 0.91286(15) 0.53302(12) 0.0312(6) Uani 1 1 d . . . . .
H20 H -0.012688 0.884567 0.505507 0.037 Uiso 1 1 calc R . . . .
C1 C 0.5671(2) 0.88929(12) 0.44709(10) 0.0230(4) Uani 1 1 d . . . . .
O1W O 0.9609(3) 0.81722(19) 0.0806(2) 0.0834(10) Uani 1 1 d . . . . .
H1WA H 0.932254 0.773038 0.084797 0.125 Uiso 1 1 d G . . . .
H1WB H 1.033565 0.816257 0.088513 0.125 Uiso 1 1 d G . . . .
C16 C 0.14025(19) 0.95416(13) 0.57404(11) 0.0263(4) Uani 1 1 d . . . . .
C19 C 0.00964(19) 0.95546(13) 0.57284(11) 0.0264(5) Uani 1 1 d . . . . .
C13 C 0.8949(2) 0.63615(15) 0.16590(11) 0.0300(5) Uani 1 1 d . . . . .
C18 C 0.3260(2) 1.00026(17) 0.60827(13) 0.0343(6) Uani 1 1 d . . . . .
H18 H 0.367064 1.035017 0.630570 0.041 Uiso 1 1 calc R . . . .
C23 C -0.0553(2) 0.99733(18) 0.61187(13) 0.0370(6) Uani 1 1 d . . . . .
H23 H -0.017553 1.027505 0.638895 0.044 Uiso 1 1 calc R . . . .
N1 N 0.6067(2) 0.78631(14) 0.37562(10) 0.0394(6) Uani 1 1 d . . . . .
C10 C 0.8568(2) 0.67823(15) 0.21882(11) 0.0314(5) Uani 1 1 d . . . . .
C22 C -0.1768(2) 0.99421(18) 0.61062(13) 0.0366(6) Uani 1 1 d . . . . .
H22 H -0.218695 1.022711 0.637216 0.044 Uiso 1 1 calc R . . . .
C17 C 0.2047(2) 1.00615(16) 0.60641(14) 0.0374(6) Uani 1 1 d . . . . .
H17 H 0.166776 1.044489 0.626607 0.045 Uiso 1 1 calc R . . . .
C15 C 0.2033(2) 0.89908(17) 0.54449(13) 0.0359(6) Uani 1 1 d . . . . .
H15 H 0.164748 0.863507 0.521855 0.043 Uiso 1 1 calc R . . . .
C14 C 0.3244(2) 0.89768(18) 0.54909(14) 0.0371(6) Uani 1 1 d . . . . .
H14 H 0.364722 0.859739 0.529569 0.045 Uiso 1 1 calc R . . . .
C11 C 0.8599(3) 0.75649(18) 0.22260(15) 0.0488(8) Uani 1 1 d . . . . .
H11 H 0.889832 0.784996 0.192389 0.059 Uiso 1 1 calc R . . . .
C2 C 0.5513(2) 0.80608(14) 0.43010(11) 0.0329(6) Uani 1 1 d . . . . .
H2 H 0.581630 0.773190 0.460578 0.039 Uiso 1 1 calc R . . . .
C3 C 0.4202(3) 0.78816(17) 0.41965(16) 0.0523(8) Uani 1 1 d . . . . .
H3AA H 0.387952 0.759008 0.451210 0.063 Uiso 0.7 1 calc R . . A 1
H3AB H 0.375374 0.834608 0.415303 0.063 Uiso 0.7 1 calc R . . A 1
H3BC H 0.400000 0.738523 0.434783 0.063 Uiso 0.3 1 calc R . . B 2
H3BD H 0.370691 0.826114 0.437558 0.063 Uiso 0.3 1 calc R . . B 2
C7 C 0.7719(3) 0.75214(17) 0.31574(12) 0.0415(7) Uani 1 1 d . . . . .
C6 C 0.7234(3) 0.78745(16) 0.36978(13) 0.0391(6) Uani 1 1 d . . . . .
C12 C 0.8179(3) 0.79313(18) 0.27191(16) 0.0530(9) Uani 1 1 d . . . . .
H12 H 0.821606 0.845814 0.274579 0.064 Uiso 1 1 calc R . . . .
C5 C 0.5200(4) 0.7676(3) 0.33084(17) 0.0617(10) Uani 1 1 d . . . . .
H5AA H 0.500675 0.812045 0.308066 0.074 Uiso 0.7 1 calc R . . C 1
H5AB H 0.548709 0.727884 0.305693 0.074 Uiso 0.7 1 calc R . . C 1
H5BC H 0.536116 0.795680 0.295896 0.074 Uiso 0.3 1 calc R . . D 2
H5BD H 0.521213 0.713703 0.322287 0.074 Uiso 0.3 1 calc R . . D 2
O2W O 1.000000 0.4517(3) 0.250000 0.127(3) Uani 1 2 d S T P . .
C8 C 0.7718(5) 0.6741(2) 0.31233(15) 0.0723(14) Uani 1 1 d . . . . .
H8 H 0.741888 0.645478 0.342519 0.087 Uiso 1 1 calc R . . . .
C9 C 0.8159(4) 0.63761(19) 0.26413(14) 0.0633(12) Uani 1 1 d . . . . .
H9 H 0.817518 0.584789 0.262854 0.076 Uiso 1 1 calc R . . . .
C4A C 0.4189(7) 0.7416(4) 0.3640(3) 0.0681(16) Uani 0.7 1 d . . . E 1
H4AA H 0.425211 0.687786 0.372294 0.082 Uiso 0.7 1 calc R . . E 1
H4AB H 0.346953 0.750478 0.342919 0.082 Uiso 0.7 1 calc R . . E 1
C4B C 0.4070(12) 0.7899(8) 0.3548(7) 0.062(4) Uani 0.3 1 d . . . E 2
H4BA H 0.346422 0.754759 0.342727 0.075 Uiso 0.3 1 calc R . . E 2
H4BB H 0.385872 0.840548 0.342093 0.075 Uiso 0.3 1 calc R . . E 2


_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
Co1 O4 2.1353(17) 6_665 ?
Co1 O1 2.0026(18) . ?
Co1 O2 2.0504(16) 4_576 ?
Co1 N2 2.1588(19) . ?
Co1 O5 2.270(2) 6_665 ?
Co1 N3 2.1549(19) 1_655 ?
O4 C13 1.264(3) . ?
O1 C1 1.240(3) . ?
O2 C1 1.247(3) . ?
N2 C18 1.337(3) . ?
N2 C14 1.337(3) . ?
O5 C13 1.248(3) . ?
N3 C21 1.335(3) . ?
N3 C22 1.343(3) . ?
O3 C6 1.231(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.388(4) . ?
C1 C2 1.527(3) . ?
O1W H1WA 0.8494 . ?
O1W H1WB 0.8505 . ?
C16 C19 1.493(3) . ?
C16 C17 1.396(4) . ?
C16 C15 1.391(4) . ?
C19 C23 1.386(4) . ?
C13 C10 1.503(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.390(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.391(4) . ?
N1 C2 1.462(4) . ?
N1 C6 1.341(4) . ?
N1 C5 1.476(4) . ?
C10 C11 1.380(4) . ?
C10 C9 1.358(4) . ?
C22 H22 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.389(4) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.403(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.550(4) . ?
C3 H3AA 0.9700 . ?
C3 H3AB 0.9700 . ?
C3 H3BC 0.9700 . ?
C3 H3BD 0.9700 . ?
C3 C4A 1.534(7) . ?
C3 C4B 1.519(16) . ?
C7 C6 1.510(4) . ?
C7 C12 1.357(5) . ?
C7 C8 1.376(5) . ?
C12 H12 0.9300 . ?
C5 H5AA 0.9700 . ?
C5 H5AB 0.9700 . ?
C5 H5BC 0.9700 . ?
C5 H5BD 0.9700 . ?
C5 C4A 1.464(8) . ?
C5 C4B 1.462(14) . ?
C8 H8 0.9300 . ?
C8 C9 1.389(4) . ?
C9 H9 0.9300 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?

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
O4 Co1 N2 93.47(8) 6_665 . ?
O4 Co1 O5 59.17(7) 6_665 6_665 ?
O4 Co1 N3 89.28(8) 6_665 1_655 ?
O1 Co1 O4 151.26(8) . 6_665 ?
O1 Co1 O2 121.74(8) . 4_576 ?
O1 Co1 N2 87.95(8) . . ?
O1 Co1 O5 92.11(8) . 6_665 ?
O1 Co1 N3 90.66(8) . 1_655 ?
O2 Co1 O4 87.00(7) 4_576 6_665 ?
O2 Co1 N2 88.65(8) 4_576 . ?
O2 Co1 O5 146.08(7) 4_576 6_665 ?
O2 Co1 N3 89.36(8) 4_576 1_655 ?
N2 Co1 O5 95.28(8) . 6_665 ?
N3 Co1 N2 176.51(8) 1_655 . ?
N3 Co1 O5 87.96(8) 1_655 6_665 ?
C13 O4 Co1 92.93(15) . 6_664 ?
C1 O1 Co1 167.5(2) . . ?
C1 O2 Co1 124.41(15) . 4_576 ?
C18 N2 Co1 122.02(17) . . ?
C18 N2 C14 116.4(2) . . ?
C14 N2 Co1 121.44(17) . . ?
C13 O5 Co1 87.21(15) . 6_664 ?
C21 N3 Co1 123.68(17) . 1_455 ?
C21 N3 C22 117.1(2) . . ?
C22 N3 Co1 119.13(17) . 1_455 ?
N3 C21 H21 118.3 . . ?
N3 C21 C20 123.3(2) . . ?
C20 C21 H21 118.3 . . ?
C21 C20 H20 120.1 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
O1 C1 O2 125.8(2) . . ?
O1 C1 C2 115.8(2) . . ?
O2 C1 C2 118.2(2) . . ?
H1WA O1W H1WB 109.5 . . ?
C17 C16 C19 121.8(2) . . ?
C15 C16 C19 121.3(2) . . ?
C15 C16 C17 116.8(2) . . ?
C20 C19 C16 121.0(2) . . ?
C23 C19 C20 116.9(2) . . ?
C23 C19 C16 122.1(2) . . ?
O4 C13 C10 118.6(2) . . ?
O5 C13 O4 120.2(2) . . ?
O5 C13 C10 121.1(2) . . ?
N2 C18 H18 118.2 . . ?
N2 C18 C17 123.7(3) . . ?
C17 C18 H18 118.2 . . ?
C19 C23 H23 120.0 . . ?
C19 C23 C22 120.0(2) . . ?
C22 C23 H23 120.0 . . ?
C2 N1 C5 112.1(3) . . ?
C6 N1 C2 121.1(2) . . ?
C6 N1 C5 126.8(3) . . ?
C11 C10 C13 122.4(3) . . ?
C9 C10 C13 118.6(2) . . ?
C9 C10 C11 118.9(3) . . ?
N3 C22 C23 122.8(3) . . ?
N3 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
N2 C14 C15 124.1(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C1 C2 H2 109.6 . . ?
C1 C2 C3 110.5(2) . . ?
N1 C2 C1 113.7(2) . . ?
N1 C2 H2 109.6 . . ?
N1 C2 C3 103.5(2) . . ?
C3 C2 H2 109.6 . . ?
C2 C3 H3AA 110.8 . . ?
C2 C3 H3AB 110.8 . . ?
C2 C3 H3BC 110.9 . . ?
C2 C3 H3BD 110.9 . . ?
H3AA C3 H3AB 108.9 . . ?
H3BC C3 H3BD 108.9 . . ?
C4A C3 C2 104.6(4) . . ?
C4A C3 H3AA 110.8 . . ?
C4A C3 H3AB 110.8 . . ?
C4B C3 C2 104.4(6) . . ?
C4B C3 H3BC 110.9 . . ?
C4B C3 H3BD 110.9 . . ?
C12 C7 C6 123.5(3) . . ?
C12 C7 C8 119.2(3) . . ?
C8 C7 C6 117.3(3) . . ?
O3 C6 N1 121.7(3) . . ?
O3 C6 C7 121.8(3) . . ?
N1 C6 C7 116.4(3) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12 119.8 . . ?
N1 C5 H5AA 111.1 . . ?
N1 C5 H5AB 111.1 . . ?
N1 C5 H5BC 110.7 . . ?
N1 C5 H5BD 110.7 . . ?
H5AA C5 H5AB 109.1 . . ?
H5BC C5 H5BD 108.8 . . ?
C4A C5 N1 103.1(4) . . ?
C4A C5 H5AA 111.1 . . ?
C4A C5 H5AB 111.1 . . ?
C4B C5 N1 105.2(6) . . ?
C4B C5 H5BC 110.7 . . ?
C4B C5 H5BD 110.7 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C3 C4A H4AA 110.6 . . ?
C3 C4A H4AB 110.6 . . ?
C5 C4A C3 105.8(4) . . ?
C5 C4A H4AA 110.6 . . ?
C5 C4A H4AB 110.6 . . ?
H4AA C4A H4AB 108.7 . . ?
C3 C4B H4BA 110.4 . . ?
C3 C4B H4BB 110.4 . . ?
C5 C4B C3 106.7(9) . . ?
C5 C4B H4BA 110.4 . . ?
C5 C4B H4BB 110.4 . . ?
H4BA C4B H4BB 108.6 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.517
_oxdiff_exptl_absorpt_empirical_full_min 0.436
####################################################################### 
# 
# 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_2-L
_database_code_depnum_ccdc_archive 'CCDC 1985394'
loop_
_audit_author_name
_audit_author_address
'Zhong-Xuan Xu'
;School of chemistry and chemical engineering, Zunyi Normal College
China
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Co N3 O5, H2 O, 0.5(O)'
_chemical_formula_sum            'C23 H22 Co N3 O6.50'
_chemical_formula_weight         503.36
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONCo
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.4166(9)
_cell_length_b                   17.5949(13)
_cell_length_c                   23.3418(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4688.8(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      4.0120
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20895
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.165
_diffrn_reflns_theta_min         3.675
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00 -61.00   0.50   72.99    --   -0.00 -38.00-180.00   56
  2  ω    -31.00  -4.00   0.50   72.99    --   -0.00 -38.00-180.00   54
  3  ω      8.00  34.00   0.50   72.99    --   -0.00  38.00-150.00   52
  4  ω    -37.00  29.00   0.50   72.99    --   -0.00 -82.00  30.00  132
  5  ω    -15.00  10.00   0.50   72.99    --   -0.00  38.00   0.00   50
  6  ω    -58.00 -20.50   0.50   72.99    --   -0.00 -82.00 -90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268006000
_diffrn_orient_matrix_UB_12      -0.0309535000
_diffrn_orient_matrix_UB_13      -0.0143881000
_diffrn_orient_matrix_UB_21      0.0049234000
_diffrn_orient_matrix_UB_22      0.0224184000
_diffrn_orient_matrix_UB_23      -0.0251423000
_diffrn_orient_matrix_UB_31      0.0558620000
_diffrn_orient_matrix_UB_32      0.0128815000
_diffrn_orient_matrix_UB_33      0.0091360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                5756
_reflns_number_total             6175
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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         0.348
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 2298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H3AA(0.7) H3AB(0.7) H3BC(0.3) H3BD(0.3) H5AA(0.7) H5AB(0.7)
 H5BC(0.3) H5BD(0.3) C4B(0.7) H4BA(0.7) H4BB(0.7) C4A(0.3) H4AA(0.3) H4AB(0.3)
3.a Free rotating group:
 O1W(H1WA,H1WB)
3.b Ternary CH refined with riding coordinates:
 C2(H2)
3.c Secondary CH2 refined with riding coordinates:
 C3(H3AA,H3AB), C3(H3BC,H3BD), C5(H5AA,H5AB), C5(H5BC,H5BD), C4B(H4BA,H4BB),
 C4A(H4AA,H4AB)
3.d Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C15(H15), C22(H22), C14(H14), C20(H20), C23(H23), C9(H9),
 C21(H21), C12(H12), C8(H8), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
Co1 Co 0.07579(3) 0.94708(2) 0.42174(2) 0.02076(9) Uani 1 1 d . . . . .
O4 O 0.40988(17) 0.56522(10) 0.83088(7) 0.0364(4) Uani 1 1 d . . . . .
O1 O 0.06665(18) 0.90275(13) 0.50072(8) 0.0434(4) Uani 1 1 d . . . . .
O2 O 0.07254(17) 0.93780(9) 0.59188(7) 0.0329(3) Uani 1 1 d . . . . .
N3 N 0.88691(17) 0.94755(12) 0.42022(8) 0.0277(4) Uani 1 1 d . . . . .
N2 N 0.26366(16) 0.95185(12) 0.42729(8) 0.0267(4) Uani 1 1 d . . . . .
O5 O 0.4055(2) 0.66935(11) 0.88113(8) 0.0405(5) Uani 1 1 d . . . . .
C18 C 0.3266(2) 0.91262(15) 0.46558(11) 0.0309(5) Uani 1 1 d . . . . .
H18 H 0.286836 0.883653 0.492629 0.037 Uiso 1 1 calc R . . . .
O3 O 0.2876(2) 0.81157(16) 0.59202(10) 0.0554(6) Uani 1 1 d . . . . .
C1 C 0.06734(19) 0.88932(12) 0.55279(9) 0.0227(4) Uani 1 1 d . . . . .
C17 C 0.4477(2) 0.91287(15) 0.46703(11) 0.0313(5) Uani 1 1 d . . . . .
H17 H 0.487352 0.884622 0.494553 0.038 Uiso 1 1 calc R . . . .
C19 C 0.64038(19) 0.95407(13) 0.42596(10) 0.0266(4) Uani 1 1 d . . . . .
O1W O 0.4607(3) 0.81700(19) 0.91979(19) 0.0843(11) Uani 1 1 d . . . . .
H1WA H 0.426946 0.774900 0.912914 0.126 Uiso 1 1 d G . . . .
H1WB H 0.533301 0.806347 0.919936 0.126 Uiso 1 1 d G . . . .
C13 C 0.3945(2) 0.63627(15) 0.83409(10) 0.0304(5) Uani 1 1 d . . . . .
C15 C 0.4447(2) 0.99769(18) 0.38825(12) 0.0373(6) Uani 1 1 d . . . . .
H15 H 0.482288 1.028156 0.361381 0.045 Uiso 1 1 calc R . . . .
C22 C 0.8261(2) 1.00032(17) 0.39151(12) 0.0356(6) Uani 1 1 d . . . . .
H22 H 0.867119 1.034834 0.368979 0.043 Uiso 1 1 calc R . . . .
C16 C 0.50996(19) 0.95558(13) 0.42712(10) 0.0263(4) Uani 1 1 d . . . . .
N1 N 0.1072(2) 0.78614(14) 0.62432(10) 0.0412(6) Uani 1 1 d . . . . .
C14 C 0.3234(2) 0.99425(19) 0.38955(12) 0.0369(6) Uani 1 1 d . . . . .
H14 H 0.281523 1.022714 0.362969 0.044 Uiso 1 1 calc R . . . .
C10 C 0.3570(2) 0.67833(15) 0.78118(10) 0.0322(5) Uani 1 1 d . . . . .
C20 C 0.7035(2) 0.89909(18) 0.45548(12) 0.0368(6) Uani 1 1 d . . . . .
H20 H 0.664890 0.863689 0.478259 0.044 Uiso 1 1 calc R . . . .
C23 C 0.7052(2) 1.00617(17) 0.39362(14) 0.0379(6) Uani 1 1 d . . . . .
H23 H 0.667178 1.044630 0.373589 0.045 Uiso 1 1 calc R . . . .
C9 C 0.3597(3) 0.75643(19) 0.77738(14) 0.0493(8) Uani 1 1 d . . . . .
H9 H 0.389283 0.784910 0.807651 0.059 Uiso 1 1 calc R . . . .
C21 C 0.8245(2) 0.89743(18) 0.45071(13) 0.0382(6) Uani 1 1 d . . . . .
H21 H 0.864806 0.859153 0.469860 0.046 Uiso 1 1 calc R . . . .
C2 C 0.0516(3) 0.80626(14) 0.56999(11) 0.0333(5) Uani 1 1 d . . . . .
H2 H 0.081773 0.773320 0.539515 0.040 Uiso 1 1 calc R . . . .
C3 C -0.0799(3) 0.78844(18) 0.58041(16) 0.0531(8) Uani 1 1 d . . . . .
H3AA H -0.124624 0.834927 0.584881 0.064 Uiso 0.7 1 calc R . . A 1
H3AB H -0.112292 0.759477 0.548808 0.064 Uiso 0.7 1 calc R . . A 1
H3BC H -0.129371 0.826464 0.562542 0.064 Uiso 0.3 1 calc R . . B 2
H3BD H -0.100254 0.738830 0.565278 0.064 Uiso 0.3 1 calc R . . B 2
C7 C 0.2722(3) 0.75197(17) 0.68418(12) 0.0415(6) Uani 1 1 d . . . . .
C6 C 0.2235(3) 0.78751(16) 0.63021(12) 0.0400(6) Uani 1 1 d . . . . .
C5 C 0.0202(4) 0.7681(3) 0.66911(16) 0.0621(10) Uani 1 1 d . . . . .
H5AA H 0.048670 0.728554 0.694488 0.075 Uiso 0.7 1 calc R . . C 1
H5AB H 0.000886 0.812778 0.691560 0.075 Uiso 0.7 1 calc R . . C 1
H5BC H 0.021321 0.714229 0.677869 0.075 Uiso 0.3 1 calc R . . D 2
H5BD H 0.036941 0.796282 0.703885 0.075 Uiso 0.3 1 calc R . . D 2
C12 C 0.2718(5) 0.6741(2) 0.68781(14) 0.0741(15) Uani 1 1 d . . . . .
H12 H 0.242043 0.645469 0.657644 0.089 Uiso 1 1 calc R . . . .
C8 C 0.3181(3) 0.79321(19) 0.72825(16) 0.0541(9) Uani 1 1 d . . . . .
H8 H 0.321721 0.845897 0.725666 0.065 Uiso 1 1 calc R . . . .
C11 C 0.3155(5) 0.63758(19) 0.73603(13) 0.0651(12) Uani 1 1 d . . . . .
H11 H 0.316409 0.584764 0.737464 0.078 Uiso 1 1 calc R . . . .
O2W O 0.500000 0.4516(3) 0.750000 0.131(3) Uani 1 2 d S T P . .
C4B C -0.0813(7) 0.7418(4) 0.6357(3) 0.0702(16) Uani 0.7 1 d . . . E 1
H4BA H -0.153447 0.750407 0.656700 0.084 Uiso 0.7 1 calc R . . E 1
H4BB H -0.074628 0.688001 0.627296 0.084 Uiso 0.7 1 calc R . . E 1
C4A C -0.0931(13) 0.7902(9) 0.6459(7) 0.066(4) Uani 0.3 1 d . . . E 2
H4AA H -0.114249 0.840790 0.658694 0.079 Uiso 0.3 1 calc R . . E 2
H4AB H -0.153438 0.754894 0.658090 0.079 Uiso 0.3 1 calc R . . E 2


_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
Co1 O4 2.1381(16) 6_564 ?
Co1 O1 2.0046(17) . ?
Co1 O2 2.0506(16) 4_576 ?
Co1 N3 2.1566(19) 1_455 ?
Co1 N2 2.1505(19) . ?
Co1 O5 2.267(2) 6_564 ?
O4 C13 1.265(3) . ?
O1 C1 1.238(3) . ?
O2 C1 1.251(3) . ?
N3 C22 1.339(3) . ?
N3 C21 1.339(3) . ?
N2 C18 1.339(3) . ?
N2 C14 1.341(3) . ?
O5 C13 1.249(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.382(3) . ?
O3 C6 1.228(4) . ?
C1 C2 1.526(3) . ?
C17 H17 0.9300 . ?
C17 C16 1.392(3) . ?
C19 C16 1.489(3) . ?
C19 C20 1.389(3) . ?
C19 C23 1.399(3) . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8501 . ?
C13 C10 1.502(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(3) . ?
C15 C14 1.386(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(4) . ?
N1 C2 1.461(3) . ?
N1 C6 1.336(4) . ?
N1 C5 1.476(4) . ?
C14 H14 0.9300 . ?
C10 C9 1.377(4) . ?
C10 C11 1.360(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(4) . ?
C23 H23 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.400(4) . ?
C21 H21 0.9300 . ?
C2 H2 0.9800 . ?
C2 C3 1.553(4) . ?
C3 H3AA 0.9700 . ?
C3 H3AB 0.9700 . ?
C3 H3BC 0.9700 . ?
C3 H3BD 0.9700 . ?
C3 C4B 1.529(7) . ?
C3 C4A 1.535(16) . ?
C7 C6 1.512(4) . ?
C7 C12 1.373(5) . ?
C7 C8 1.364(5) . ?
C5 H5AA 0.9700 . ?
C5 H5AB 0.9700 . ?
C5 H5BC 0.9700 . ?
C5 H5BD 0.9700 . ?
C5 C4B 1.472(8) . ?
C5 C4A 1.456(16) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(4) . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?

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
O4 Co1 N3 93.47(7) 6_564 1_455 ?
O4 Co1 N2 89.28(7) 6_564 . ?
O4 Co1 O5 59.12(7) 6_564 6_564 ?
O1 Co1 O4 151.27(8) . 6_564 ?
O1 Co1 O2 121.74(8) . 4_576 ?
O1 Co1 N3 87.97(8) . 1_455 ?
O1 Co1 N2 90.67(8) . . ?
O1 Co1 O5 92.16(8) . 6_564 ?
O2 Co1 O4 86.99(7) 4_576 6_564 ?
O2 Co1 N3 88.60(8) 4_576 1_455 ?
O2 Co1 N2 89.36(8) 4_576 . ?
O2 Co1 O5 146.03(7) 4_576 6_564 ?
N3 Co1 O5 95.19(8) 1_455 6_564 ?
N2 Co1 N3 176.49(8) . 1_455 ?
N2 Co1 O5 88.09(8) . 6_564 ?
C13 O4 Co1 92.98(14) . 6_565 ?
C1 O1 Co1 167.6(2) . . ?
C1 O2 Co1 124.16(15) . 4_576 ?
C22 N3 Co1 121.97(16) . 1_655 ?
C21 N3 Co1 121.39(17) . 1_655 ?
C21 N3 C22 116.5(2) . . ?
C18 N2 Co1 123.77(16) . . ?
C18 N2 C14 116.9(2) . . ?
C14 N2 Co1 119.32(16) . . ?
C13 O5 Co1 87.47(15) . 6_565 ?
N2 C18 H18 118.3 . . ?
N2 C18 C17 123.5(2) . . ?
C17 C18 H18 118.3 . . ?
O1 C1 O2 125.9(2) . . ?
O1 C1 C2 116.1(2) . . ?
O2 C1 C2 117.83(19) . . ?
C18 C17 H17 120.1 . . ?
C18 C17 C16 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C20 C19 C16 121.5(2) . . ?
C20 C19 C23 116.7(2) . . ?
C23 C19 C16 121.8(2) . . ?
H1WA O1W H1WB 104.5 . . ?
O4 C13 C10 118.5(2) . . ?
O5 C13 O4 119.9(2) . . ?
O5 C13 C10 121.5(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(2) . . ?
N3 C22 H22 118.3 . . ?
N3 C22 C23 123.4(2) . . ?
C23 C22 H22 118.3 . . ?
C17 C16 C19 120.9(2) . . ?
C15 C16 C17 116.8(2) . . ?
C15 C16 C19 122.3(2) . . ?
C2 N1 C5 112.0(3) . . ?
C6 N1 C2 121.1(2) . . ?
C6 N1 C5 126.9(3) . . ?
N2 C14 C15 123.2(2) . . ?
N2 C14 H14 118.4 . . ?
C15 C14 H14 118.4 . . ?
C9 C10 C13 122.6(3) . . ?
C11 C10 C13 118.5(2) . . ?
C11 C10 C9 118.9(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C23 H23 120.1 . . ?
C22 C23 C19 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
N3 C21 C20 124.0(3) . . ?
N3 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
C1 C2 H2 109.5 . . ?
C1 C2 C3 110.4(2) . . ?
N1 C2 C1 114.1(2) . . ?
N1 C2 H2 109.5 . . ?
N1 C2 C3 103.6(2) . . ?
C3 C2 H2 109.5 . . ?
C2 C3 H3AA 110.8 . . ?
C2 C3 H3AB 110.8 . . ?
C2 C3 H3BC 110.9 . . ?
C2 C3 H3BD 110.9 . . ?
H3AA C3 H3AB 108.9 . . ?
H3BC C3 H3BD 108.9 . . ?
C4B C3 C2 104.5(4) . . ?
C4B C3 H3AA 110.8 . . ?
C4B C3 H3AB 110.8 . . ?
C4A C3 C2 104.3(6) . . ?
C4A C3 H3BC 110.9 . . ?
C4A C3 H3BD 110.9 . . ?
C12 C7 C6 117.6(3) . . ?
C8 C7 C6 123.3(3) . . ?
C8 C7 C12 119.1(3) . . ?
O3 C6 N1 121.6(2) . . ?
O3 C6 C7 121.9(3) . . ?
N1 C6 C7 116.3(3) . . ?
N1 C5 H5AA 111.2 . . ?
N1 C5 H5AB 111.2 . . ?
N1 C5 H5BC 110.5 . . ?
N1 C5 H5BD 110.5 . . ?
H5AA C5 H5AB 109.1 . . ?
H5BC C5 H5BD 108.7 . . ?
C4B C5 N1 102.8(3) . . ?
C4B C5 H5AA 111.2 . . ?
C4B C5 H5AB 111.2 . . ?
C4A C5 N1 106.0(6) . . ?
C4A C5 H5BC 110.5 . . ?
C4A C5 H5BD 110.5 . . ?
C7 C12 H12 119.6 . . ?
C7 C12 C11 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C9 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C3 C4B H4BA 110.6 . . ?
C3 C4B H4BB 110.6 . . ?
C5 C4B C3 105.7(4) . . ?
C5 C4B H4BA 110.6 . . ?
C5 C4B H4BB 110.6 . . ?
H4BA C4B H4BB 108.7 . . ?
C3 C4A H4AA 110.5 . . ?
C3 C4A H4AB 110.5 . . ?
C5 C4A C3 106.1(9) . . ?
C5 C4A H4AA 110.5 . . ?
C5 C4A H4AB 110.5 . . ?
H4AA C4A H4AB 108.7 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.036
_oxdiff_exptl_absorpt_empirical_full_min 0.388
