# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1044059'
_audit_update_record             
;
2015-01-18 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 Cu N3 O4'
_chemical_formula_weight         450.93

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.890(5)
_cell_length_b                   16.186(11)
_cell_length_c                   15.193(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.385(10)
_cell_angle_gamma                90.00
_cell_volume                     1919(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6524
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.48

_exptl_crystal_description       bulk
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    1.174
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5394
_exptl_absorpt_correction_T_max  0.8165
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12518
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4325
_reflns_number_gt                3566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4325
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7295(3) 0.74402(14) 0.17617(15) 0.0328(5) Uani 1 1 d . . .
C2 C 0.8738(3) 0.77580(18) 0.14548(19) 0.0460(6) Uani 1 1 d . . .
H2 H 0.8822 0.7775 0.0851 0.055 Uiso 1 1 calc R . .
C3 C 1.0035(4) 0.80449(17) 0.2082(2) 0.0512(7) Uani 1 1 d . . .
H3 H 1.1016 0.8265 0.1899 0.061 Uiso 1 1 calc R . .
C4 C 0.9907(3) 0.80119(18) 0.2992(2) 0.0533(8) Uani 1 1 d . . .
H4 H 1.0809 0.8208 0.3401 0.064 Uiso 1 1 calc R . .
C5 C 0.8471(3) 0.76946(18) 0.32966(17) 0.0429(6) Uani 1 1 d . . .
H5 H 0.8400 0.7667 0.3902 0.052 Uiso 1 1 calc R . .
C6 C 0.7141(3) 0.74187(15) 0.26660(15) 0.0321(5) Uani 1 1 d . . .
C7 C 0.4810(3) 0.68776(13) 0.19336(14) 0.0277(4) Uani 1 1 d . . .
C8 C 0.3125(3) 0.64920(14) 0.17040(13) 0.0292(4) Uani 1 1 d . . .
C9 C 0.2361(3) 0.64951(17) 0.08116(15) 0.0384(5) Uani 1 1 d . . .
H9 H 0.2909 0.6766 0.0392 0.046 Uiso 1 1 calc R . .
C10 C 0.0823(3) 0.61084(18) 0.05401(16) 0.0462(6) Uani 1 1 d . . .
H10 H 0.0366 0.6095 -0.0060 0.055 Uiso 1 1 calc R . .
C11 C -0.0044(3) 0.57375(19) 0.11692(17) 0.0485(6) Uani 1 1 d . . .
H11 H -0.1095 0.5482 0.0993 0.058 Uiso 1 1 calc R . .
C12 C 0.0659(3) 0.57496(17) 0.20589(16) 0.0400(5) Uani 1 1 d . . .
H12 H 0.0051 0.5518 0.2478 0.048 Uiso 1 1 calc R . .
C13 C 0.2256(3) 0.61015(14) 0.23406(14) 0.0310(5) Uani 1 1 d . . .
C14 C 0.2552(3) 0.54589(15) 0.37283(14) 0.0340(5) Uani 1 1 d . . .
H14 H 0.2042 0.5013 0.3407 0.041 Uiso 1 1 calc R . .
C15 C 0.2824(3) 0.53749(14) 0.46716(14) 0.0322(5) Uani 1 1 d . . .
C16 C 0.2265(3) 0.46294(16) 0.50242(16) 0.0431(6) Uani 1 1 d . . .
H16 H 0.1816 0.4214 0.4636 0.052 Uiso 1 1 calc R . .
C17 C 0.2368(3) 0.45046(16) 0.59276(16) 0.0442(6) Uani 1 1 d . . .
H17 H 0.1996 0.4011 0.6148 0.053 Uiso 1 1 calc R . .
C18 C 0.3040(3) 0.51316(16) 0.65049(15) 0.0349(5) Uani 1 1 d . . .
C20 C 0.3515(3) 0.60050(14) 0.52622(14) 0.0297(4) Uani 1 1 d . . .
C21 C 0.3611(3) 0.58669(15) 0.61860(14) 0.0337(5) Uani 1 1 d . . .
H21 H 0.4061 0.6274 0.6584 0.040 Uiso 1 1 calc R . .
C1A C 0.6132(5) 0.9402(2) 0.4187(2) 0.0724(10) Uani 1 1 d . . .
H1A1 H 0.7208 0.9341 0.3969 0.109 Uiso 1 1 calc R . .
H1A2 H 0.6331 0.9466 0.4822 0.109 Uiso 1 1 calc R . .
H1A3 H 0.5548 0.9881 0.3922 0.109 Uiso 1 1 calc R . .
C2A C 0.5045(3) 0.86447(16) 0.39474(14) 0.0342(5) Uani 1 1 d . . .
Cu1 Cu 0.44557(3) 0.696043(17) 0.382483(15) 0.02869(13) Uani 1 1 d . . .
N1 N 0.5558(2) 0.70622(12) 0.27591(13) 0.0295(4) Uani 1 1 d . . .
N2 N 0.5816(3) 0.70905(13) 0.13242(13) 0.0336(4) Uani 1 1 d . . .
H2A H 0.5575 0.7020 0.0759 0.040 Uiso 1 1 calc R . .
N3 N 0.2940(2) 0.60922(12) 0.32652(11) 0.0295(4) Uani 1 1 d . . .
O1 O 0.3096(3) 0.49829(13) 0.73877(11) 0.0512(5) Uani 1 1 d . . .
H1 H 0.3331 0.5412 0.7667 0.077 Uiso 1 1 calc R . .
O3 O 0.4052(2) 0.67122(11) 0.49878(10) 0.0392(4) Uani 1 1 d . . .
O4 O 0.5490(2) 0.79903(10) 0.43733(11) 0.0371(4) Uani 1 1 d . . .
O2A O 0.3860(2) 0.86798(14) 0.33352(13) 0.0504(5) 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
C1 N2 1.377(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.397(3) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 N1 1.401(3) . ?
C7 N1 1.340(3) . ?
C7 N2 1.349(3) . ?
C7 C8 1.464(3) . ?
C8 C9 1.401(3) . ?
C8 C13 1.413(3) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 N3 1.429(3) . ?
C14 N3 1.305(3) . ?
C14 C15 1.424(3) . ?
C14 H14 0.9300 . ?
C15 C20 1.414(3) . ?
C15 C16 1.417(3) . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.394(4) . ?
C17 H17 0.9300 . ?
C18 O1 1.357(3) . ?
C18 C21 1.385(3) . ?
C20 O3 1.309(3) . ?
C20 C21 1.412(3) . ?
C21 H21 0.9300 . ?
C1A C2A 1.510(4) . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
C2A O2A 1.220(3) . ?
C2A O4 1.264(3) . ?
Cu1 O3 1.8839(19) . ?
Cu1 N1 1.953(2) . ?
Cu1 N3 1.9574(19) . ?
Cu1 O4 1.9851(19) . ?
N2 H2A 0.8600 . ?
O1 H1 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 131.9(2) . . ?
N2 C1 C6 105.98(19) . . ?
C2 C1 C6 122.1(2) . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.5(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 N1 131.2(2) . . ?
C1 C6 N1 108.4(2) . . ?
N1 C7 N2 111.3(2) . . ?
N1 C7 C8 125.35(19) . . ?
N2 C7 C8 123.4(2) . . ?
C9 C8 C13 118.8(2) . . ?
C9 C8 C7 118.4(2) . . ?
C13 C8 C7 122.79(18) . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.8(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.5(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C8 118.7(2) . . ?
C12 C13 N3 119.5(2) . . ?
C8 C13 N3 121.75(18) . . ?
N3 C14 C15 127.2(2) . . ?
N3 C14 H14 116.4 . . ?
C15 C14 H14 116.4 . . ?
C20 C15 C16 119.1(2) . . ?
C20 C15 C14 123.9(2) . . ?
C16 C15 C14 116.9(2) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 118.8(2) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
O1 C18 C21 122.2(2) . . ?
O1 C18 C17 116.6(2) . . ?
C21 C18 C17 121.2(2) . . ?
O3 C20 C21 118.8(2) . . ?
O3 C20 C15 122.8(2) . . ?
C21 C20 C15 118.4(2) . . ?
C18 C21 C20 120.7(2) . . ?
C18 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C2A C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 109.5 . . ?
C2A C1A H1A3 109.5 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O2A C2A O4 123.7(2) . . ?
O2A C2A C1A 119.4(2) . . ?
O4 C2A C1A 116.8(2) . . ?
O3 Cu1 N1 162.18(9) . . ?
O3 Cu1 N3 94.48(8) . . ?
N1 Cu1 N3 91.03(8) . . ?
O3 Cu1 O4 84.31(8) . . ?
N1 Cu1 O4 94.11(8) . . ?
N3 Cu1 O4 166.64(8) . . ?
C7 N1 C6 105.93(19) . . ?
C7 N1 Cu1 124.68(16) . . ?
C6 N1 Cu1 129.00(16) . . ?
C7 N2 C1 108.4(2) . . ?
C7 N2 H2A 125.8 . . ?
C1 N2 H2A 125.8 . . ?
C14 N3 C13 116.99(19) . . ?
C14 N3 Cu1 120.41(15) . . ?
C13 N3 Cu1 122.57(15) . . ?
C18 O1 H1 109.5 . . ?
C20 O3 Cu1 126.28(15) . . ?
C2A O4 Cu1 114.97(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 C2 C3 -178.1(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C4 C5 C6 C1 2.1(4) . . . . ?
C4 C5 C6 N1 179.1(3) . . . . ?
N2 C1 C6 C5 177.0(2) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
N2 C1 C6 N1 -0.6(3) . . . . ?
C2 C1 C6 N1 -179.7(2) . . . . ?
N1 C7 C8 C9 166.8(2) . . . . ?
N2 C7 C8 C9 -13.5(3) . . . . ?
N1 C7 C8 C13 -14.7(3) . . . . ?
N2 C7 C8 C13 165.1(2) . . . . ?
C13 C8 C9 C10 -2.0(4) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
C8 C9 C10 C11 3.1(4) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 -2.3(5) . . . . ?
C11 C12 C13 C8 3.4(4) . . . . ?
C11 C12 C13 N3 -179.4(3) . . . . ?
C9 C8 C13 C12 -1.3(3) . . . . ?
C7 C8 C13 C12 -179.8(2) . . . . ?
C9 C8 C13 N3 -178.5(2) . . . . ?
C7 C8 C13 N3 3.0(3) . . . . ?
N3 C14 C15 C20 2.8(4) . . . . ?
N3 C14 C15 C16 178.9(2) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C14 C15 C16 C17 -175.9(2) . . . . ?
C15 C16 C17 C18 0.1(4) . . . . ?
C16 C17 C18 O1 179.2(2) . . . . ?
C16 C17 C18 C21 -0.5(4) . . . . ?
C16 C15 C20 O3 -179.7(2) . . . . ?
C14 C15 C20 O3 -3.6(3) . . . . ?
C16 C15 C20 C21 -0.4(3) . . . . ?
C14 C15 C20 C21 175.6(2) . . . . ?
O1 C18 C21 C20 -179.3(2) . . . . ?
C17 C18 C21 C20 0.5(4) . . . . ?
O3 C20 C21 C18 179.3(2) . . . . ?
C15 C20 C21 C18 0.0(3) . . . . ?
N2 C7 N1 C6 0.2(3) . . . . ?
C8 C7 N1 C6 -180.0(2) . . . . ?
N2 C7 N1 Cu1 173.55(14) . . . . ?
C8 C7 N1 Cu1 -6.7(3) . . . . ?
C5 C6 N1 C7 -177.0(3) . . . . ?
C1 C6 N1 C7 0.2(3) . . . . ?
C5 C6 N1 Cu1 10.0(4) . . . . ?
C1 C6 N1 Cu1 -172.70(16) . . . . ?
O3 Cu1 N1 C7 134.8(2) . . . . ?
N3 Cu1 N1 C7 26.67(19) . . . . ?
O4 Cu1 N1 C7 -141.00(19) . . . . ?
O3 Cu1 N1 C6 -53.5(4) . . . . ?
N3 Cu1 N1 C6 -161.6(2) . . . . ?
O4 Cu1 N1 C6 30.7(2) . . . . ?
N1 C7 N2 C1 -0.6(3) . . . . ?
C8 C7 N2 C1 179.6(2) . . . . ?
C2 C1 N2 C7 179.7(3) . . . . ?
C6 C1 N2 C7 0.7(3) . . . . ?
C15 C14 N3 C13 -168.4(2) . . . . ?
C15 C14 N3 Cu1 13.6(3) . . . . ?
C12 C13 N3 C14 32.8(3) . . . . ?
C8 C13 N3 C14 -150.1(2) . . . . ?
C12 C13 N3 Cu1 -149.25(19) . . . . ?
C8 C13 N3 Cu1 27.9(3) . . . . ?
O3 Cu1 N3 C14 -21.86(18) . . . . ?
N1 Cu1 N3 C14 141.18(18) . . . . ?
O4 Cu1 N3 C14 -106.1(3) . . . . ?
O3 Cu1 N3 C13 160.25(17) . . . . ?
N1 Cu1 N3 C13 -36.71(17) . . . . ?
O4 Cu1 N3 C13 76.0(4) . . . . ?
C21 C20 O3 Cu1 167.22(16) . . . . ?
C15 C20 O3 Cu1 -13.5(3) . . . . ?
N1 Cu1 O3 C20 -84.9(3) . . . . ?
N3 Cu1 O3 C20 22.8(2) . . . . ?
O4 Cu1 O3 C20 -170.6(2) . . . . ?
O2A C2A O4 Cu1 12.3(3) . . . . ?
C1A C2A O4 Cu1 -163.8(2) . . . . ?
O3 Cu1 O4 C2A -134.14(17) . . . . ?
N1 Cu1 O4 C2A 63.67(17) . . . . ?
N3 Cu1 O4 C2A -48.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.088
