# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_STAM-NMe2
_database_code_depnum_ccdc_archive 'CCDC 1938059'
loop_
_audit_author_name
_audit_author_address
'David B. Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-03 deposited with the CCDC.	2019-08-23 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 Cu N O5'
_chemical_formula_sum            'C10 H11 Cu N O5'
_chemical_formula_weight         288.74
_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      trigonal
_space_group_IT_number           164
_space_group_name_H-M_alt        P-3m1
_space_group_name_Hall           '-P 3 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'

_cell_length_a                   18.5382(5)
_cell_length_b                   18.5382(5)
_cell_length_c                   6.7599(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2011.90(12)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    8019
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.6280
_cell_measurement_theta_min      2.1770
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             882
_exptl_crystal_recrystallization_method Hydrothermal
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26670
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.935
_diffrn_reflns_theta_min         2.197
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00   0.00  360
  2  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00  90.00  360
  3  ω   -100.00  80.00   0.50   10.00    --  -10.00  45.00 180.00  360
;
_diffrn_measurement_device       'AFC10: Fixed chi 2 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0211459000
_diffrn_orient_matrix_UB_12      0.0265681000
_diffrn_orient_matrix_UB_13      0.0810173000
_diffrn_orient_matrix_UB_21      0.0248767000
_diffrn_orient_matrix_UB_22      0.0326560000
_diffrn_orient_matrix_UB_23      -0.0666589000
_diffrn_orient_matrix_UB_31      -0.0297584000
_diffrn_orient_matrix_UB_32      0.0133964000
_diffrn_orient_matrix_UB_33      0.0018751000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1394
_reflns_number_total             1842
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)
;
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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         0.431
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.124
_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)+(0.0536P)²+0.3573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 O1W(H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_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
Cu1 Cu 0.47619(2) 0.52381(2) 0.34416(5) 0.01171(15) Uani 1 2 d S T P . .
O1W O 0.43601(8) 0.56399(8) 0.0904(3) 0.0249(6) Uani 1 2 d S T P . .
H1WB H 0.395249 0.521309 0.029752 0.037 Uiso 1 1 d GR . . . .
O2 O 0.55943(13) 0.58859(10) 0.7560(3) 0.0284(4) Uani 1 1 d . . . . .
O1 O 0.51998(14) 0.62877(11) 0.4880(3) 0.0360(5) Uani 1 1 d . . . . .
N1 N 0.6755(2) 0.83775(11) 1.2156(5) 0.0289(8) Uani 1 2 d S T P . .
C1 C 0.55014(14) 0.64104(14) 0.6593(3) 0.0152(5) Uani 1 1 d . . . . .
C2 C 0.57591(14) 0.72332(14) 0.7526(3) 0.0155(5) Uani 1 1 d . . . . .
C5 C 0.6367(2) 0.81833(11) 1.0325(5) 0.0193(7) Uani 1 2 d S T P . .
C4 C 0.61473(15) 0.74245(14) 0.9367(3) 0.0176(5) Uani 1 1 d . . . . .
H4 H 0.626696 0.703694 0.999037 0.021 Uiso 1 1 calc R . . . .
C3 C 0.5572(2) 0.77858(10) 0.6579(5) 0.0173(7) Uani 1 2 d S T P . .
H3 H 0.531970 0.765985 0.530721 0.021 Uiso 1 2 calc RS T P . .
C6 C 0.71023(19) 0.92145(16) 1.2910(4) 0.0314(7) Uani 1 1 d . . . . .
H6A H 0.756397 0.959927 1.206053 0.047 Uiso 1 1 calc GR . . . .
H6B H 0.730760 0.923958 1.425843 0.047 Uiso 1 1 calc GR . . . .
H6C H 0.667111 0.937310 1.292256 0.047 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 2.6032(7) 7_666 ?
Cu1 O1W 2.146(2) . ?
Cu1 O2 1.9649(16) 7_666 ?
Cu1 O2 1.9649(16) 4_556 ?
Cu1 O1 1.9524(18) . ?
Cu1 O1 1.9523(18) 10_665 ?
O1W H1WB 0.876(5) 10_665 ?
O1W H1WB 0.8759 . ?
O2 C1 1.253(3) . ?
O1 C1 1.256(3) . ?
N1 C5 1.386(4) . ?
N1 C6 1.443(3) . ?
N1 C6 1.443(3) 12_565 ?
C1 C2 1.491(3) . ?
C2 C4 1.392(3) . ?
C2 C3 1.392(3) . ?
C5 C4 1.411(3) . ?
C5 C4 1.411(3) 12_565 ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 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
O1W Cu1 Cu1 179.02(7) . 7_666 ?
O2 Cu1 Cu1 84.86(5) 7_666 7_666 ?
O2 Cu1 Cu1 84.86(5) 4_556 7_666 ?
O2 Cu1 O1W 95.83(7) 7_666 . ?
O2 Cu1 O1W 95.83(7) 4_556 . ?
O2 Cu1 O2 88.58(12) 7_666 4_556 ?
O1 Cu1 Cu1 83.82(5) . 7_666 ?
O1 Cu1 Cu1 83.82(5) 10_665 7_666 ?
O1 Cu1 O1W 95.50(7) . . ?
O1 Cu1 O1W 95.50(7) 10_665 . ?
O1 Cu1 O2 168.65(7) 10_665 4_556 ?
O1 Cu1 O2 89.66(9) 10_665 7_666 ?
O1 Cu1 O2 168.65(7) . 7_666 ?
O1 Cu1 O2 89.66(9) . 4_556 ?
O1 Cu1 O1 89.86(13) 10_665 . ?
Cu1 O1W H1WB 110.7(4) . 10_665 ?
Cu1 O1W H1WB 110.7 . . ?
H1WB O1W H1WB 124.0 . 10_665 ?
C1 O2 Cu1 122.66(15) . 7_666 ?
C1 O1 Cu1 124.42(16) . . ?
C5 N1 C6 119.29(16) . 12_565 ?
C5 N1 C6 119.29(16) . . ?
C6 N1 C6 116.9(3) 12_565 . ?
O2 C1 O1 124.2(2) . . ?
O2 C1 C2 118.4(2) . . ?
O1 C1 C2 117.4(2) . . ?
C4 C2 C1 119.9(2) . . ?
C3 C2 C1 119.2(2) . . ?
C3 C2 C4 120.8(2) . . ?
N1 C5 C4 121.47(15) . . ?
N1 C5 C4 121.47(15) . 12_565 ?
C4 C5 C4 117.0(3) . 12_565 ?
C2 C4 C5 121.3(2) . . ?
C2 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C2 C3 C2 118.9(3) 12_565 . ?
C2 C3 H3 120.6 12_565 . ?
C2 C3 H3 120.6 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.186 305.8 10.4 ?
2 0.333 0.667 -0.872 134.2 36.1 ?
3 0.667 0.333 -0.309 134.2 30.8 ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.639
