# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1833499'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Cu N2 O5, N O3'
_chemical_formula_sum            'C19 H19 Cu N3 O8'
_chemical_formula_weight         480.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0010 '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'
Cu Cu 0.3510 1.1760 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0100 0.0050 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.8332(4)
_cell_length_b                   9.26780(10)
_cell_length_c                   24.5582(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4058.84(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7442
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4830
_cell_measurement_theta_min      1.5640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.985
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'oval-cut emerald color'
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.786
_diffrn_reflns_Laue_measured_fraction_max 0.729
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17084
_diffrn_reflns_point_group_measured_fraction_full 0.786
_diffrn_reflns_point_group_measured_fraction_max 0.729
_diffrn_reflns_theta_full        23.899
_diffrn_reflns_theta_max         25.470
_diffrn_reflns_theta_min         1.576
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.786
_diffrn_measured_fraction_theta_max 0.729
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00 360.00   1.00    2.00    --    0.00   0.00   0.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0071790000
_diffrn_orient_matrix_UB_12      0.0363016000
_diffrn_orient_matrix_UB_13      0.0232636000
_diffrn_orient_matrix_UB_21      -0.0001552000
_diffrn_orient_matrix_UB_22      0.0627534000
_diffrn_orient_matrix_UB_23      -0.0139720000
_diffrn_orient_matrix_UB_31      -0.0371747000
_diffrn_orient_matrix_UB_32      -0.0072923000
_diffrn_orient_matrix_UB_33      -0.0044125000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.67522
_diffrn_source                   synchrotron
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3014
_reflns_number_total             3204
_reflns_odcompleteness_completeness 72.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.47
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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         0.865
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3204
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0687
_refine_ls_restrained_S_all      1.086
_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)+(0.1107P)²+8.3969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1920
_refine_ls_wR_factor_ref         0.1948
_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) groups
2. Restrained distances
 C00V-C00U
 1.55 with sigma of 0.005
 O004-H004
 0.85 with sigma of 0.01
 C00U-H004
 1.936529 with sigma of 0.02
 Cu01-H004
 2.744332 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00C), C00R(H00D,H00F), C00U(H00G,H00K)
3.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00N(H00N), C00P(H00P), C00S(H00S)
3.c Idealised Me refined as rotating group:
 C00V(H00M,H00O,H00Q)
;
_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
Cu01 Cu 0.45237(4) 0.90772(6) 0.52257(2) 0.0455(3) Uani 1 1 d D . . . .
O3 O 0.6176(2) 1.0234(4) 0.53331(14) 0.0577(10) Uani 1 1 d . . . . .
O1 O 1.0123(2) 0.2411(4) 0.97183(12) 0.0577(10) Uani 1 1 d . . . . .
O5 O 0.3758(2) 0.7871(4) 0.57091(14) 0.0626(11) Uani 1 1 d D . . . .
H004 H 0.3718(19) 0.795(6) 0.6057(4) 0.094 Uiso 1 1 d DR . . . .
O2 O 0.9311(3) 0.0833(4) 0.93537(16) 0.0671(11) Uani 1 1 d . . . . .
O4 O 0.5377(2) 0.8634(5) 0.57072(13) 0.0611(11) Uani 1 1 d . . . . .
N1 N 0.8980(3) 0.5759(4) 0.75969(18) 0.0566(12) Uani 1 1 d . . . . .
N2 N 0.8384(3) 0.6862(5) 0.69328(16) 0.0554(12) Uani 1 1 d . . . . .
C16 C 0.6629(3) 0.8652(5) 0.60077(17) 0.0468(13) Uani 1 1 d . . . . .
O1N O 0.4095(4) 0.8794(6) 0.6797(2) 0.1040(19) Uani 1 1 d . . . . .
C8 C 0.8326(4) 0.6065(5) 0.73852(19) 0.0526(14) Uani 1 1 d . . . . .
H00B H 0.787202 0.576168 0.753237 0.063 Uiso 1 1 calc R . . . .
C11 C 0.7776(3) 0.7467(5) 0.66271(18) 0.0507(14) Uani 1 1 d . . . . .
C17 C 0.6014(4) 0.9225(5) 0.56545(17) 0.0485(14) Uani 1 1 d . . . . .
C6 C 0.8751(3) 0.3540(5) 0.8103(2) 0.0547(14) Uani 1 1 d . . . . .
H00E H 0.842240 0.323829 0.783206 0.066 Uiso 1 1 calc R . . . .
C1 C 0.9623(3) 0.2048(5) 0.93820(19) 0.0501(14) Uani 1 1 d . . . . .
C7 C 0.9102(3) 0.4880(5) 0.80734(19) 0.0551(14) Uani 1 1 d . . . . .
C13 C 0.7058(4) 0.7100(6) 0.67332(18) 0.0598(16) Uani 1 1 d . . . . .
H00H H 0.695049 0.645163 0.701145 0.072 Uiso 1 1 calc R . . . .
C4 C 0.8906(3) 0.2668(5) 0.85482(18) 0.0526(13) Uani 1 1 d . . . . .
H00I H 0.867507 0.177121 0.857720 0.063 Uiso 1 1 calc R . . . .
C15 C 0.6481(3) 0.7693(7) 0.64262(19) 0.0624(15) Uani 1 1 d . . . . .
H00J H 0.598762 0.744089 0.650301 0.075 Uiso 1 1 calc R . . . .
C2 C 0.9397(3) 0.3113(5) 0.89483(19) 0.0503(13) Uani 1 1 d . . . . .
C3 C 0.9712(3) 0.4491(6) 0.8933(2) 0.0548(13) Uani 1 1 d . . . . .
H00L H 1.001798 0.480881 0.921465 0.066 Uiso 1 1 calc R . . . .
N1N N 0.3563(5) 0.9301(6) 0.7072(2) 0.093(2) Uani 1 1 d . . . . .
C5 C 0.9563(3) 0.5384(6) 0.8490(2) 0.0577(15) Uani 1 1 d . . . . .
H00N H 0.976847 0.630522 0.847224 0.069 Uiso 1 1 calc R . . . .
C10 C 0.9172(4) 0.7112(7) 0.6803(2) 0.0649(17) Uani 1 1 d . . . . .
H00A H 0.927838 0.813656 0.677800 0.078 Uiso 1 1 calc R . . . .
H00C H 0.930723 0.665279 0.646243 0.078 Uiso 1 1 calc R . . . .
C14 C 0.7368(4) 0.9012(6) 0.5906(2) 0.0688(18) Uani 1 1 d . . . . .
H00P H 0.747944 0.966337 0.562964 0.083 Uiso 1 1 calc R . . . .
O2N O 0.3773(4) 0.9820(7) 0.7522(2) 0.126(2) Uani 1 1 d . . . . .
C9 C 0.9596(4) 0.6423(8) 0.7285(2) 0.075(2) Uani 1 1 d . . . . .
H00D H 0.995207 0.570408 0.716151 0.090 Uiso 1 1 calc R . . . .
H00F H 0.985639 0.714548 0.749944 0.090 Uiso 1 1 calc R . . . .
C12 C 0.7941(4) 0.8420(7) 0.6208(2) 0.0731(19) Uani 1 1 d . . . . .
H00S H 0.843634 0.865807 0.613164 0.088 Uiso 1 1 calc R . . . .
O3N O 0.2946(5) 0.9350(16) 0.6948(4) 0.237(7) Uani 1 1 d . . . . .
C18 C 0.2986(7) 0.7516(11) 0.5520(5) 0.147(4) Uani 1 1 d D . . . .
H00G H 0.296080 0.758165 0.512588 0.176 Uiso 1 1 calc R . . . .
H00K H 0.263039 0.819753 0.567210 0.176 Uiso 1 1 calc R . . . .
C19 C 0.2789(7) 0.5994(11) 0.5701(5) 0.158(5) Uani 1 1 d D . . . .
H00M H 0.315858 0.533164 0.556614 0.237 Uiso 1 1 calc GR . . . .
H00O H 0.230500 0.573582 0.556043 0.237 Uiso 1 1 calc GR . . . .
H00Q H 0.277882 0.595392 0.609178 0.237 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
Cu01 Cu01 2.6534(13) 5_676 ?
Cu01 O3 1.962(3) 5_676 ?
Cu01 O1 1.962(3) 2_664 ?
Cu01 O5 2.127(4) . ?
Cu01 O2 1.964(3) 6_567 ?
Cu01 O4 1.971(4) . ?
O3 C17 1.257(6) . ?
O1 C1 1.261(7) . ?
O5 H004 0.861(10) . ?
O5 C18 1.490(12) . ?
O2 C1 1.259(6) . ?
O4 C17 1.267(7) . ?
N1 C8 1.307(7) . ?
N1 C7 1.443(6) . ?
N1 C9 1.473(7) . ?
N2 C8 1.339(6) . ?
N2 C11 1.432(7) . ?
N2 C10 1.459(8) . ?
C16 C17 1.496(7) . ?
C16 C15 1.385(7) . ?
C16 C14 1.382(9) . ?
O1N N1N 1.255(8) . ?
C8 H00B 0.9300 . ?
C11 C13 1.350(8) . ?
C11 C12 1.387(7) . ?
C6 H00E 0.9300 . ?
C6 C7 1.392(8) . ?
C6 C4 1.387(6) . ?
C1 C2 1.507(6) . ?
C7 C5 1.393(8) . ?
C13 H00H 0.9300 . ?
C13 C15 1.389(8) . ?
C4 H00I 0.9300 . ?
C4 C2 1.380(7) . ?
C15 H00J 0.9300 . ?
C2 C3 1.396(8) . ?
C3 H00L 0.9300 . ?
C3 C5 1.392(7) . ?
N1N O2N 1.264(8) . ?
N1N O3N 1.142(10) . ?
C5 H00N 0.9300 . ?
C10 H00A 0.9700 . ?
C10 H00C 0.9700 . ?
C10 C9 1.543(7) . ?
C14 H00P 0.9300 . ?
C14 C12 1.377(8) . ?
C9 H00D 0.9700 . ?
C9 H00F 0.9700 . ?
C12 H00S 0.9300 . ?
C18 H00G 0.9700 . ?
C18 H00K 0.9700 . ?
C18 C19 1.520(5) . ?
C19 H00M 0.9600 . ?
C19 H00O 0.9600 . ?
C19 H00Q 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
O3 Cu01 Cu01 84.56(12) 5_676 5_676 ?
O3 Cu01 O1 89.35(16) 5_676 2_664 ?
O3 Cu01 O5 98.82(17) 5_676 . ?
O3 Cu01 O2 88.58(18) 5_676 6_567 ?
O3 Cu01 O4 168.21(18) 5_676 . ?
O1 Cu01 Cu01 88.98(12) 2_664 5_676 ?
O1 Cu01 O5 101.00(16) 2_664 . ?
O1 Cu01 O2 167.97(17) 2_664 6_567 ?
O1 Cu01 O4 89.24(17) 2_664 . ?
O5 Cu01 Cu01 169.45(10) . 5_676 ?
O2 Cu01 Cu01 79.03(13) 6_567 5_676 ?
O2 Cu01 O5 91.02(16) 6_567 . ?
O2 Cu01 O4 90.37(18) 6_567 . ?
O4 Cu01 Cu01 83.71(13) . 5_676 ?
O4 Cu01 O5 92.94(17) . . ?
C17 O3 Cu01 122.3(4) . 5_676 ?
C1 O1 Cu01 117.1(3) . 2_665 ?
Cu01 O5 H004 124.4(19) . . ?
C18 O5 Cu01 122.3(5) . . ?
C18 O5 H004 104.5(18) . . ?
C1 O2 Cu01 128.8(4) . 6_647 ?
C17 O4 Cu01 122.7(3) . . ?
C8 N1 C7 125.4(4) . . ?
C8 N1 C9 111.6(4) . . ?
C7 N1 C9 123.0(5) . . ?
C8 N2 C11 126.4(5) . . ?
C8 N2 C10 110.0(4) . . ?
C11 N2 C10 123.5(4) . . ?
C15 C16 C17 121.3(5) . . ?
C14 C16 C17 120.6(5) . . ?
C14 C16 C15 118.1(5) . . ?
N1 C8 N2 112.4(5) . . ?
N1 C8 H00B 123.8 . . ?
N2 C8 H00B 123.8 . . ?
C13 C11 N2 121.2(4) . . ?
C13 C11 C12 120.3(5) . . ?
C12 C11 N2 118.6(5) . . ?
O3 C17 O4 126.3(5) . . ?
O3 C17 C16 117.3(6) . . ?
O4 C17 C16 116.4(5) . . ?
C7 C6 H00E 120.9 . . ?
C4 C6 H00E 120.9 . . ?
C4 C6 C7 118.1(5) . . ?
O1 C1 C2 118.5(5) . . ?
O2 C1 O1 126.0(4) . . ?
O2 C1 C2 115.4(5) . . ?
C6 C7 N1 118.6(5) . . ?
C6 C7 C5 121.7(4) . . ?
C5 C7 N1 119.7(5) . . ?
C11 C13 H00H 120.1 . . ?
C11 C13 C15 119.9(5) . . ?
C15 C13 H00H 120.1 . . ?
C6 C4 H00I 119.6 . . ?
C2 C4 C6 120.9(5) . . ?
C2 C4 H00I 119.6 . . ?
C16 C15 C13 121.1(6) . . ?
C16 C15 H00J 119.5 . . ?
C13 C15 H00J 119.5 . . ?
C4 C2 C1 118.5(5) . . ?
C4 C2 C3 120.6(4) . . ?
C3 C2 C1 120.7(5) . . ?
C2 C3 H00L 120.4 . . ?
C5 C3 C2 119.3(5) . . ?
C5 C3 H00L 120.4 . . ?
O1N N1N O2N 112.9(8) . . ?
O3N N1N O1N 126.9(9) . . ?
O3N N1N O2N 120.2(9) . . ?
C7 C5 H00N 120.4 . . ?
C3 C5 C7 119.1(5) . . ?
C3 C5 H00N 120.4 . . ?
N2 C10 H00A 111.0 . . ?
N2 C10 H00C 111.0 . . ?
N2 C10 C9 103.8(4) . . ?
H00A C10 H00C 109.0 . . ?
C9 C10 H00A 111.0 . . ?
C9 C10 H00C 111.0 . . ?
C16 C14 H00P 119.5 . . ?
C12 C14 C16 120.9(5) . . ?
C12 C14 H00P 119.5 . . ?
N1 C9 C10 101.9(5) . . ?
N1 C9 H00D 111.4 . . ?
N1 C9 H00F 111.4 . . ?
C10 C9 H00D 111.4 . . ?
C10 C9 H00F 111.4 . . ?
H00D C9 H00F 109.3 . . ?
C11 C12 H00S 120.1 . . ?
C14 C12 C11 119.8(6) . . ?
C14 C12 H00S 120.1 . . ?
O5 C18 H00G 109.9 . . ?
O5 C18 H00K 109.9 . . ?
O5 C18 C19 109.1(9) . . ?
H00G C18 H00K 108.3 . . ?
C19 C18 H00G 109.9 . . ?
C19 C18 H00K 109.9 . . ?
C18 C19 H00M 109.5 . . ?
C18 C19 H00O 109.5 . . ?
C18 C19 H00Q 109.5 . . ?
H00M C19 H00O 109.5 . . ?
H00M C19 H00Q 109.5 . . ?
H00O C19 H00Q 109.5 . . ?

_vrf_PLAT029_1                   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.786 Why?
RESPONSE: Low data completeness is caused by the synchrotron setup features,
 in particular, only omega scans were possible, so a part of reciprocal sphere 
 was inaccessible during the measurement.
 The purpose of this dataset is to indicate the ease of nitrate anion location at room temperature,
 and this purpose is reached with the data quality available.

;

_vrf_PLAT230_1                   
;
PROBLEM: Hirshfeld Test Diff for O5 --C18 . 8.1 s.u.
RESPONSE:  Hirshfield test difference for O5-C18 is high because C18 belongs to the part of ethanol molecule
 dangling in the pore, which is more disordered rather than O5 which is directly bound to the copper site.

;



_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 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.899
####################################################################### 
# 
# 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_cusp5_pl
_database_code_depnum_ccdc_archive 'CCDC 1833500'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 Cu N2 O5, N O3'
_chemical_formula_sum            'C19 H19 Cu N3 O8'
_chemical_formula_weight         480.91
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.7049(15)
_cell_length_b                   9.2515(9)
_cell_length_c                   24.5663(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4023.9(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3358
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.11
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'irregular shape'
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23222
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.275
_diffrn_reflns_theta_max         23.275
_diffrn_reflns_theta_min         2.301
_diffrn_ambient_temperature      99.92
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2188
_reflns_number_total             2890
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.075
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.065
_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)+(0.0556P)²+24.6838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1628
_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) groups
2. Restrained distances
 C19-C18
 1.51 with sigma of 0.002
3. Rigid body (RIGU) restrains
 O1N, N1N, O2N, O3N
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15), C17(H17)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.45202(4) 1.09214(8) 0.52258(3) 0.0246(3) Uani 1 1 d . . . . .
O1 O 0.1186(3) -0.0245(5) 0.96638(19) 0.0352(12) Uani 1 1 d . . . . .
O5 O 0.3749(3) 1.2129(5) 0.5712(2) 0.0379(12) Uani 1 1 d . . . . .
H2 H 0.369(5) 1.175(9) 0.604(3) 0.057 Uiso 1 1 d R . . . .
O3 O 0.5126(3) 0.7579(5) 0.52751(18) 0.0358(12) Uani 1 1 d . . . . .
O2 O 0.0380(2) 0.1348(6) 0.92922(17) 0.0374(12) Uani 1 1 d . . . . .
O4 O 0.4306(3) 0.9153(6) 0.5638(2) 0.0454(14) Uani 1 1 d . . . . .
N1 N 0.3392(3) 0.3148(6) 0.8065(2) 0.0332(14) Uani 1 1 d . . . . .
N2 N 0.3987(3) 0.4238(6) 0.7394(2) 0.0345(14) Uani 1 1 d . . . . .
O1N O 0.4103(4) 1.1158(7) 0.6788(2) 0.0675(18) Uani 1 1 d . U . . .
C2 C 0.1642(3) 0.1350(7) 0.8993(2) 0.0261(15) Uani 1 1 d . . . . .
C11 C 0.4099(4) 0.5110(8) 0.6920(3) 0.0308(17) Uani 1 1 d . . . . .
C16 C 0.4396(3) 0.6871(7) 0.6041(3) 0.0278(16) Uani 1 1 d . . . . .
C7 C 0.2790(3) 0.2530(8) 0.8371(3) 0.0290(16) Uani 1 1 d . . . . .
C13 C 0.3754(4) 0.6444(7) 0.6888(3) 0.0313(16) Uani 1 1 d . . . . .
H5 H 0.342322 0.676270 0.716712 0.038 Uiso 1 1 calc R . . . .
C8 C 0.3335(4) 0.3930(7) 0.7613(3) 0.0338(17) Uani 1 1 d . . . . .
H6 H 0.286678 0.423506 0.746330 0.041 Uiso 1 1 calc R . . . .
C15 C 0.3900(3) 0.7308(8) 0.6441(3) 0.0312(17) Uani 1 1 d . . . . .
H7 H 0.365410 0.821656 0.640897 0.037 Uiso 1 1 calc R . . . .
C6 C 0.2060(4) 0.2879(8) 0.8266(3) 0.0363(19) Uani 1 1 d . . . . .
H8 H 0.194414 0.353409 0.798036 0.044 Uiso 1 1 calc R . . . .
C14 C 0.4718(3) 0.5487(7) 0.6058(3) 0.0307(16) Uani 1 1 d . . . . .
H9 H 0.502982 0.515442 0.576966 0.037 Uiso 1 1 calc R . . . .
C17 C 0.4625(4) 0.7940(8) 0.5608(3) 0.0292(16) Uani 1 1 d . . . . .
C4 C 0.1488(4) 0.2288(9) 0.8571(3) 0.0401(19) Uani 1 1 d . . . . .
H11 H 0.097910 0.252833 0.849016 0.048 Uiso 1 1 calc R . . . .
C1 C 0.1019(4) 0.0761(7) 0.9349(3) 0.0283(16) Uani 1 1 d . . . . .
C12 C 0.4570(4) 0.4612(8) 0.6506(3) 0.0346(17) Uani 1 1 d . . . . .
H13 H 0.478933 0.367662 0.652892 0.042 Uiso 1 1 calc R . . . .
N1N N 0.3575(4) 1.0712(8) 0.7066(3) 0.0586(18) Uani 1 1 d . U . . .
O2N O 0.3761(5) 1.0210(8) 0.7528(3) 0.095(2) Uani 1 1 d . U . . .
C9 C 0.4195(4) 0.2901(9) 0.8191(3) 0.041(2) Uani 1 1 d . . . . .
H14A H 0.430393 0.185597 0.822643 0.049 Uiso 1 1 calc R . . . .
H14B H 0.434064 0.339562 0.853260 0.049 Uiso 1 1 calc R . . . .
C3 C 0.2380(4) 0.0990(8) 0.9097(3) 0.046(2) Uani 1 1 d . . . . .
H15 H 0.249576 0.032870 0.938076 0.055 Uiso 1 1 calc R . . . .
C10 C 0.4611(4) 0.3554(10) 0.7700(3) 0.049(2) Uani 1 1 d . . . . .
H16A H 0.499006 0.427718 0.781559 0.059 Uiso 1 1 calc R . . . .
H16B H 0.486261 0.279610 0.748056 0.059 Uiso 1 1 calc R . . . .
C5 C 0.2958(4) 0.1588(10) 0.8790(3) 0.056(3) Uani 1 1 d . . . . .
H17 H 0.346921 0.134852 0.886682 0.067 Uiso 1 1 calc R . . . .
O3N O 0.2959(4) 1.062(2) 0.6954(4) 0.224(8) Uani 1 1 d . U . . .
C18 C 0.2988(6) 1.2475(12) 0.5548(6) 0.107(4) Uani 1 1 d D . . . .
H18A H 0.262972 1.183341 0.574175 0.128 Uiso 1 1 calc R . . . .
H18B H 0.293180 1.229803 0.515269 0.128 Uiso 1 1 calc R . . . .
C19 C 0.2795(7) 1.4027(12) 0.5671(6) 0.124(5) Uani 1 1 d D . . . .
H19A H 0.313479 1.466516 0.546666 0.187 Uiso 1 1 calc GR . . . .
H19B H 0.285400 1.420707 0.606135 0.187 Uiso 1 1 calc GR . . . .
H19C H 0.227169 1.421974 0.556313 0.187 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 Cu1 2.6503(16) 5_676 ?
Cu1 O1 1.965(4) 2_564 ?
Cu1 O5 2.131(5) . ?
Cu1 O3 1.957(4) 5_676 ?
Cu1 O2 1.968(4) 6_667 ?
Cu1 O4 1.961(5) . ?
O1 C1 1.246(8) . ?
O5 H2 0.89(8) . ?
O5 C18 1.443(11) . ?
O3 C17 1.252(8) . ?
O2 C1 1.263(8) . ?
O4 C17 1.258(8) . ?
N1 C7 1.425(8) . ?
N1 C8 1.329(8) . ?
N1 C9 1.473(8) . ?
N2 C11 1.430(8) . ?
N2 C8 1.304(8) . ?
N2 C10 1.477(8) . ?
O1N N1N 1.229(8) . ?
C2 C4 1.379(9) . ?
C2 C1 1.509(9) . ?
C2 C3 1.372(10) . ?
C11 C13 1.378(10) . ?
C11 C12 1.395(10) . ?
C16 C15 1.378(9) . ?
C16 C14 1.401(10) . ?
C16 C17 1.508(9) . ?
C7 C6 1.357(9) . ?
C7 C5 1.380(9) . ?
C13 H5 0.9500 . ?
C13 C15 1.382(9) . ?
C8 H6 0.9500 . ?
C15 H7 0.9500 . ?
C6 H8 0.9500 . ?
C6 C4 1.373(9) . ?
C14 H9 0.9500 . ?
C14 C12 1.390(9) . ?
C4 H11 0.9500 . ?
C12 H13 0.9500 . ?
N1N O2N 1.269(9) . ?
N1N O3N 1.129(10) . ?
C9 H14A 0.9900 . ?
C9 H14B 0.9900 . ?
C9 C10 1.538(9) . ?
C3 H15 0.9500 . ?
C3 C5 1.387(10) . ?
C10 H16A 0.9900 . ?
C10 H16B 0.9900 . ?
C5 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.506(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
O1 Cu1 Cu1 84.77(14) 2_564 5_676 ?
O1 Cu1 O5 98.80(19) 2_564 . ?
O1 Cu1 O2 168.1(2) 2_564 6_667 ?
O5 Cu1 Cu1 169.38(15) . 5_676 ?
O3 Cu1 Cu1 89.29(15) 5_676 5_676 ?
O3 Cu1 O1 89.30(19) 5_676 2_564 ?
O3 Cu1 O5 100.7(2) 5_676 . ?
O3 Cu1 O2 89.4(2) 5_676 6_667 ?
O3 Cu1 O4 167.9(2) 5_676 . ?
O2 Cu1 Cu1 83.41(14) 6_667 5_676 ?
O2 Cu1 O5 93.05(19) 6_667 . ?
O4 Cu1 Cu1 78.67(15) . 5_676 ?
O4 Cu1 O1 88.5(2) . 2_564 ?
O4 Cu1 O5 91.4(2) . . ?
O4 Cu1 O2 90.4(2) . 6_667 ?
C1 O1 Cu1 121.6(4) . 2_565 ?
Cu1 O5 H2 112(5) . . ?
C18 O5 Cu1 123.9(6) . . ?
C18 O5 H2 104(5) . . ?
C17 O3 Cu1 116.6(4) . 5_676 ?
C1 O2 Cu1 122.7(4) . 6_547 ?
C17 O4 Cu1 128.8(4) . . ?
C7 N1 C9 123.2(5) . . ?
C8 N1 C7 127.2(5) . . ?
C8 N1 C9 109.5(5) . . ?
C11 N2 C10 123.5(5) . . ?
C8 N2 C11 125.5(5) . . ?
C8 N2 C10 111.1(5) . . ?
C4 C2 C1 121.2(6) . . ?
C3 C2 C4 118.7(6) . . ?
C3 C2 C1 120.1(6) . . ?
C13 C11 N2 119.4(6) . . ?
C13 C11 C12 121.2(6) . . ?
C12 C11 N2 119.4(6) . . ?
C15 C16 C14 120.4(6) . . ?
C15 C16 C17 118.8(6) . . ?
C14 C16 C17 120.7(6) . . ?
C6 C7 N1 121.1(6) . . ?
C6 C7 C5 119.9(6) . . ?
C5 C7 N1 119.0(6) . . ?
C11 C13 H5 120.6 . . ?
C11 C13 C15 118.8(7) . . ?
C15 C13 H5 120.6 . . ?
N1 C8 H6 123.3 . . ?
N2 C8 N1 113.3(6) . . ?
N2 C8 H6 123.3 . . ?
C16 C15 C13 121.0(6) . . ?
C16 C15 H7 119.5 . . ?
C13 C15 H7 119.5 . . ?
C7 C6 H8 119.9 . . ?
C7 C6 C4 120.2(6) . . ?
C4 C6 H8 119.9 . . ?
C16 C14 H9 120.7 . . ?
C12 C14 C16 118.6(6) . . ?
C12 C14 H9 120.7 . . ?
O3 C17 O4 126.4(6) . . ?
O3 C17 C16 118.4(6) . . ?
O4 C17 C16 115.1(6) . . ?
C2 C4 H11 119.5 . . ?
C6 C4 C2 121.0(6) . . ?
C6 C4 H11 119.5 . . ?
O1 C1 O2 127.0(6) . . ?
O1 C1 C2 117.1(6) . . ?
O2 C1 C2 115.9(6) . . ?
C11 C12 H13 120.1 . . ?
C14 C12 C11 119.8(6) . . ?
C14 C12 H13 120.1 . . ?
O1N N1N O2N 115.0(8) . . ?
O3N N1N O1N 128.8(10) . . ?
O3N N1N O2N 116.1(10) . . ?
N1 C9 H14A 111.0 . . ?
N1 C9 H14B 111.0 . . ?
N1 C9 C10 103.6(5) . . ?
H14A C9 H14B 109.0 . . ?
C10 C9 H14A 111.0 . . ?
C10 C9 H14B 111.0 . . ?
C2 C3 H15 119.8 . . ?
C2 C3 C5 120.3(6) . . ?
C5 C3 H15 119.8 . . ?
N2 C10 C9 102.1(5) . . ?
N2 C10 H16A 111.4 . . ?
N2 C10 H16B 111.4 . . ?
C9 C10 H16A 111.4 . . ?
C9 C10 H16B 111.4 . . ?
H16A C10 H16B 109.2 . . ?
C7 C5 C3 119.8(6) . . ?
C7 C5 H17 120.1 . . ?
C3 C5 H17 120.1 . . ?
O5 C18 H18A 109.3 . . ?
O5 C18 H18B 109.3 . . ?
O5 C18 C19 111.5(10) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
_vrf_THETM01_cusp5_pl            
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
Calculated sin(theta_max)/wavelength = 0.5560
RESPONSE: The relatively low sine(theta_max)/wavelength is caused by the
 relatively small crystal size,as we had to break the 200 um crystals 
 for meausurement. A whole 200um crystal, measured at the synchrotron, 
 shows sine(theta_max)/wavelength = 0.637.
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cusp5m_pl
_database_code_depnum_ccdc_archive 'CCDC 1833501'
_audit_update_record             
;
2018-03-29 deposited with the CCDC.
2018-05-18 downloaded from the CCDC.
;
_audit_creation_date             2018-03-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 Cu N2 O5, N O3, 0.84(O)'
_chemical_formula_sum            'C17 H13 Cu N3 O8.88'
_chemical_formula_weight         464.84
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.610(4)
_cell_length_b                   8.957(2)
_cell_length_c                   25.681(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3820.7(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.200
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1763 before and 0.0838 after correction.
The Ratio of minimum to maximum transmission is 0.7568.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1488
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23016
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        18.846
_diffrn_reflns_theta_max         18.846
_diffrn_reflns_theta_min         2.703
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1142
_reflns_number_total             1494
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         1494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0872
_refine_ls_restrained_S_all      1.202
_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)+73.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1834
_refine_ls_wR_factor_ref         0.2022
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3) = Uanis(C4) = Uanis(C6) = Uanis(C5) = Uanis(C2) = Uanis(C1)
Uanis(C13) = Uanis(C15) = Uanis(C14) = Uanis(C12) = Uanis(C10) = Uanis(C11)
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C13(H13), C12(H12), C9(H9), C5(H5), C3(H3), C11(H11), C4(H4)
;
_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 0.44736(12) 0.0928(2) 0.52103(7) 0.0486(8) Uani 1 1 d . . . . .
O4 O 0.5366(7) 0.1385(13) 0.5681(4) 0.058(3) Uani 1 1 d . . . . .
O3 O 0.6253(7) -0.0194(12) 0.5330(5) 0.055(3) Uani 1 1 d . . . . .
O1 O 1.0144(7) 0.7557(13) 0.9730(4) 0.058(3) Uani 1 1 d . . . . .
O5 O 0.3560(7) 0.2108(13) 0.5643(4) 0.068(3) Uani 1 1 d . . . . .
O2 O 0.9230(7) 0.9099(15) 0.9395(4) 0.070(4) Uani 1 1 d . . . . .
N2 N 0.8450(8) 0.3139(16) 0.6992(6) 0.057(4) Uani 1 1 d . . . . .
C16 C 0.6680(11) 0.137(2) 0.5999(7) 0.065(2) Uani 1 1 d . . . . .
N1 N 0.9019(10) 0.4141(16) 0.7689(6) 0.064(4) Uani 1 1 d . . . . .
O1N O 0.6547(10) 0.5208(17) 0.7627(6) 0.107(6) Uani 1 1 d . . . . .
C11 C 0.7839(10) 0.254(2) 0.6665(7) 0.065(2) Uani 1 1 d . . . . .
C2 C 0.9372(11) 0.6757(19) 0.8994(6) 0.058(2) Uani 1 1 d . . . . .
C1 C 0.9614(12) 0.789(2) 0.9417(7) 0.048(5) Uani 1 1 d . . . . .
C17 C 0.6044(12) 0.081(2) 0.5646(6) 0.044(4) Uani 1 1 d . . . . .
C7 C 0.9112(11) 0.4996(19) 0.8152(7) 0.058(2) Uani 1 1 d . . . . .
C14 C 0.7460(11) 0.125(2) 0.5898(6) 0.065(2) Uani 1 1 d . . . . .
H2 H 0.761533 0.074623 0.558802 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9719(10) 0.5377(18) 0.8985(6) 0.058(2) Uani 1 1 d . . . . .
H14 H 1.004063 0.503399 0.926659 0.070 Uiso 1 1 calc R . . . .
C4 C 0.8840(10) 0.722(2) 0.8608(6) 0.058(2) Uani 1 1 d . . . . .
H13 H 0.856257 0.814420 0.864009 0.070 Uiso 1 1 calc R . . . .
C5 C 0.9584(10) 0.4490(19) 0.8549(6) 0.058(2) Uani 1 1 d . . . . .
H12 H 0.982208 0.352780 0.852798 0.070 Uiso 1 1 calc R . . . .
C8 C 0.8352(12) 0.389(2) 0.7436(8) 0.063(5) Uani 1 1 d . . . . .
H9 H 0.784083 0.421647 0.755749 0.075 Uiso 1 1 calc R . . . .
C10 C 0.9303(10) 0.284(2) 0.6922(7) 0.068(6) Uani 1 1 d . . . . .
H7A H 0.951701 0.339737 0.661796 0.082 Uiso 1 1 calc R . . . .
H7B H 0.940223 0.176396 0.686980 0.082 Uiso 1 1 calc R . . . .
C12 C 0.8059(11) 0.180(2) 0.6213(6) 0.065(2) Uani 1 1 d . . . . .
H5 H 0.860994 0.167904 0.612270 0.078 Uiso 1 1 calc R . . . .
C15 C 0.6473(11) 0.213(2) 0.6448(7) 0.065(2) Uani 1 1 d . . . . .
H3 H 0.592042 0.224925 0.653508 0.078 Uiso 1 1 calc R . . . .
C6 C 0.8721(10) 0.6343(18) 0.8184(6) 0.058(2) Uani 1 1 d . . . . .
H11 H 0.837070 0.665644 0.791263 0.070 Uiso 1 1 calc R . . . .
O2N O 0.5755(15) 0.590(2) 0.8234(7) 0.146(8) Uani 1 1 d . . . . .
C13 C 0.7059(10) 0.271(2) 0.6775(7) 0.065(2) Uani 1 1 d . . . . .
H4 H 0.690420 0.323959 0.707975 0.078 Uiso 1 1 calc R . . . .
N1N N 0.6460(15) 0.571(3) 0.8086(11) 0.115(8) Uani 1 1 d . . . . .
C9 C 0.9691(11) 0.339(2) 0.7424(7) 0.080(6) Uani 1 1 d . . . . .
H8A H 0.989717 0.254112 0.763350 0.096 Uiso 1 1 calc R . . . .
H8B H 1.013790 0.408894 0.735224 0.096 Uiso 1 1 calc R . . . .
O1W O 0.7681(10) 0.454(2) 0.9478(7) 0.127(11) Uani 0.84(4) 1 d . . . . .
O3N O 0.7011(15) 0.584(5) 0.8324(8) 0.35(3) Uani 1 1 d . . . . .


_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 Cu1 2.644(4) 5_656 ?
Cu1 O4 1.955(11) . ?
Cu1 O3 1.953(11) 5_656 ?
Cu1 O1 1.941(11) 2_664 ?
Cu1 O5 2.158(11) . ?
Cu1 O2 1.968(12) 6_547 ?
O4 C17 1.241(19) . ?
O3 C17 1.262(18) . ?
O1 C1 1.228(19) . ?
O2 C1 1.262(19) . ?
N2 C11 1.42(2) . ?
N2 C8 1.34(2) . ?
N2 C10 1.45(2) . ?
C16 C17 1.48(2) . ?
C16 C14 1.33(2) . ?
C16 C15 1.38(2) . ?
N1 C7 1.42(2) . ?
N1 C8 1.30(2) . ?
N1 C9 1.47(2) . ?
O1N N1N 1.27(3) . ?
C11 C12 1.39(2) . ?
C11 C13 1.33(2) . ?
C2 C1 1.54(2) . ?
C2 C3 1.36(2) . ?
C2 C4 1.39(2) . ?
C7 C5 1.37(2) . ?
C7 C6 1.37(2) . ?
C14 C12 1.37(2) . ?
C3 C5 1.39(2) . ?
C4 C6 1.36(2) . ?
C10 C9 1.52(2) . ?
C15 C13 1.39(2) . ?
O2N N1N 1.24(2) . ?
N1N O3N 1.11(3) . ?

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 Cu1 Cu1 83.3(4) . 5_656 ?
O4 Cu1 O5 96.5(5) . . ?
O4 Cu1 O2 90.7(5) . 6_547 ?
O3 Cu1 Cu1 84.7(4) 5_656 5_656 ?
O3 Cu1 O4 167.9(5) 5_656 . ?
O3 Cu1 O5 95.5(5) 5_656 . ?
O3 Cu1 O2 87.6(5) 5_656 6_547 ?
O1 Cu1 Cu1 87.9(4) 2_664 5_656 ?
O1 Cu1 O4 89.9(5) 2_664 . ?
O1 Cu1 O3 89.2(5) 2_664 5_656 ?
O1 Cu1 O5 102.4(5) 2_664 . ?
O1 Cu1 O2 167.5(5) 2_664 6_547 ?
O5 Cu1 Cu1 169.7(3) . 5_656 ?
O2 Cu1 Cu1 79.8(4) 6_547 5_656 ?
O2 Cu1 O5 89.9(5) 6_547 . ?
C17 O4 Cu1 123.8(11) . . ?
C17 O3 Cu1 121.8(11) . 5_656 ?
C1 O1 Cu1 118.9(12) . 2_665 ?
C1 O2 Cu1 126.2(11) . 6_667 ?
C11 N2 C10 123.7(14) . . ?
C8 N2 C11 127.4(16) . . ?
C8 N2 C10 108.5(14) . . ?
C14 C16 C17 123.4(16) . . ?
C14 C16 C15 116.6(17) . . ?
C15 C16 C17 120.0(16) . . ?
C7 N1 C9 123.4(15) . . ?
C8 N1 C7 126.9(17) . . ?
C8 N1 C9 109.7(14) . . ?
C12 C11 N2 119.1(16) . . ?
C13 C11 N2 121.7(16) . . ?
C13 C11 C12 119.2(17) . . ?
C3 C2 C1 119.8(17) . . ?
C3 C2 C4 121.8(16) . . ?
C4 C2 C1 118.2(16) . . ?
O1 C1 O2 126.7(17) . . ?
O1 C1 C2 119.5(16) . . ?
O2 C1 C2 113.8(17) . . ?
O4 C17 O3 126.3(16) . . ?
O4 C17 C16 117.7(17) . . ?
O3 C17 C16 116.0(17) . . ?
C5 C7 N1 120.6(16) . . ?
C5 C7 C6 121.2(16) . . ?
C6 C7 N1 118.2(16) . . ?
C16 C14 C12 124.2(17) . . ?
C2 C3 C5 117.6(17) . . ?
C6 C4 C2 119.4(17) . . ?
C7 C5 C3 120.3(17) . . ?
N1 C8 N2 114.1(16) . . ?
N2 C10 C9 104.5(14) . . ?
C14 C12 C11 118.3(17) . . ?
C16 C15 C13 120.9(16) . . ?
C4 C6 C7 119.3(17) . . ?
C11 C13 C15 120.7(17) . . ?
O2N N1N O1N 116(3) . . ?
O3N N1N O1N 117(3) . . ?
O3N N1N O2N 127(3) . . ?
N1 C9 C10 102.5(14) . . ?

_vrf_THETM01_cusp5m_pl           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.4545
RESPONSE:  Crystal size was too small to obtain sufficient intensity at high angles.
 This explains low sine(theta_max)/wavelength value. However this crystal 
 structure is not used to precisely describe atomic positions 
 and bond lenghts, instead it is  used for packing comparison with
 a parent structure which was measured correctly.
;
_vrf_REFNR01_cusp5m_pl           
;
PROBLEM: Ratio of reflections to parameters is < 8 for a
centrosymmetric structure
sine(theta)/lambda 0.4545
Proportion of unique data used 1.0000
Ratio reflections to parameters 7.0472
RESPONSE: Low data completeness due to the reasons indicated above
;
_vrf_PLAT088_cusp5m_pl           
;
PROBLEM: Poor Data / Parameter Ratio .................... 7.05 Note
RESPONSE:Low data completeness due to the reasons indicated above
;
_vrf_PLAT341_cusp5m_pl           
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02333 Ang.
RESPONSE:Low data completeness due to the reasons indicated above
;
_vrf_PLAT430_cusp5m_pl           
;
PROBLEM: Short Inter D...A Contact O1W ..O5 2.64 Ang.
RESPONSE:It is expected due to hydrogen bonding described in the manuscript
;


_olex2_submission_special_instructions 'No special instructions were received'
