# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1944930'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriquez-Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-03-01 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-08-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H2 Cu N3 O'
_chemical_formula_sum            'C5 H2 Cu N3 O'
_chemical_formula_weight         183.64
_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           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   8.056(3)
_cell_length_b                   10.787(3)
_cell_length_c                   6.0093(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     522.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    718
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.317
_cell_measurement_theta_min      2.528
_shelx_estimated_absorpt_T_max   0.686
_shelx_estimated_absorpt_T_min   0.640
_exptl_absorpt_coefficient_mu    4.082
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.5610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0696 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.7531. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_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  0.0736
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        23.307
_diffrn_reflns_theta_max         23.307
_diffrn_reflns_theta_min         2.528
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                346
_reflns_number_total             418
_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       'Bruker Apex3, 2016'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         418
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.030
_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)+(0.0238P)²+0.3366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
;
_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 -0.10906(10) 0.23787(6) 0.250000 0.0137(3) Uani 1 2 d S TU P . .
C1 C 0.0529(9) 0.4733(5) 0.250000 0.0120(14) Uani 1 2 d S TU P . .
H1 H -0.059314 0.500239 0.250000 0.014 Uiso 1 2 calc RS T P . .
C2 C 0.3284(9) 0.5226(5) 0.250000 0.0096(11) Uani 1 2 d S TU P . .
H2 H 0.415325 0.582078 0.250000 0.012 Uiso 1 2 calc RS T P . .
C3 C 0.3674(9) 0.3988(5) 0.250000 0.0119(12) Uani 1 2 d S TU P . .
C4 C 0.2392(9) 0.3051(5) 0.250000 0.0104(10) Uani 1 2 d S TU P . .
C5 C 0.5374(10) 0.3613(5) 0.250000 0.0105(14) Uani 1 2 d S TU P . .
N1 N 0.0772(7) 0.3511(4) 0.250000 0.0125(12) Uani 1 2 d S TU P . .
N2 N 0.1683(7) 0.5621(4) 0.250000 0.0123(12) Uani 1 2 d S TU P . .
N3 N 0.6719(8) 0.3269(5) 0.250000 0.0174(14) Uani 1 2 d S TU P . .
O1 O 0.2671(6) 0.1923(3) 0.250000 0.0159(12) Uani 1 2 d S TU P . .


_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 3.0160(9) 7_565 ?
Cu1 Cu1 3.0160(9) 7_566 ?
Cu1 N1 1.935(5) . ?
Cu1 N2 1.955(5) 3_545 ?
Cu1 N3 2.009(6) 1_455 ?
C1 H1 0.9500 . ?
C1 N1 1.332(8) . ?
C1 N2 1.335(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(8) . ?
C2 N2 1.358(8) . ?
C3 C4 1.446(9) . ?
C3 C5 1.428(10) . ?
C4 N1 1.397(9) . ?
C4 O1 1.237(7) . ?
C5 N3 1.145(9) . ?

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
Cu1 Cu1 Cu1 170.04(5) 7_566 7_565 ?
N1 Cu1 Cu1 86.86(2) . 7_566 ?
N1 Cu1 Cu1 86.86(2) . 7_565 ?
N1 Cu1 N2 143.3(2) . 3_545 ?
N1 Cu1 N3 112.3(2) . 1_455 ?
N2 Cu1 Cu1 94.83(2) 3_545 7_565 ?
N2 Cu1 Cu1 94.83(3) 3_545 7_566 ?
N2 Cu1 N3 104.4(2) 3_545 1_455 ?
N3 Cu1 Cu1 87.622(18) 1_455 7_566 ?
N3 Cu1 Cu1 87.622(18) 1_455 7_565 ?
N1 C1 H1 116.3 . . ?
N1 C1 N2 127.4(6) . . ?
N2 C1 H1 116.3 . . ?
C3 C2 H2 119.2 . . ?
N2 C2 H2 119.2 . . ?
N2 C2 C3 121.6(6) . . ?
C2 C3 C4 121.1(7) . . ?
C2 C3 C5 119.7(6) . . ?
C5 C3 C4 119.1(5) . . ?
N1 C4 C3 114.8(5) . . ?
O1 C4 C3 123.9(7) . . ?
O1 C4 N1 121.3(6) . . ?
N3 C5 C3 177.5(7) . . ?
C1 N1 Cu1 120.7(5) . . ?
C1 N1 C4 119.3(6) . . ?
C4 N1 Cu1 120.0(4) . . ?
C1 N2 Cu1 121.7(4) . 3 ?
C1 N2 C2 115.8(5) . . ?
C2 N2 Cu1 122.4(4) . 3 ?
C5 N3 Cu1 170.4(5) . 1_655 ?



# start Validation Reply Form
_vrf_THETM01_compound1           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The sample diffracted very weakly and at high angles
the reflections were completely absent. Despite the quality of the data, the
composition and connectivity are not in doubt.
;
_vrf_PLAT088_compound1           
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.84 Note  
RESPONSE: See _vrf_THETM01_compound1
;
# end Validation Reply Form

_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_avg112_0p9_
_database_code_depnum_ccdc_archive 'CCDC 1993341'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriguez Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

_audit_creation_date             2020-03-13T09:38:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C5 H2 Cu N3 O'
_chemical_formula_weight         183.64

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_Int_Tables_number      57
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'
_cell_length_a                   8.0286(8)
_cell_length_b                   10.776(10)
_cell_length_c                   5.8800(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     508.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    455
_cell_measurement_theta_min      1.751
_cell_measurement_theta_max      16.795
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    2.398
_exptl_crystal_F_000             360
_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.07735
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         900000
_diffrn_ambient_environment      'collected in a Diamond Anvil Cell'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49276
_diffrn_source                   synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_reflns_number            1253
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         16.776
_diffrn_reflns_theta_full        16.776
_diffrn_measured_fraction_theta_max 0.398
_diffrn_measured_fraction_theta_full 0.397
_diffrn_reflns_Laue_measured_fraction_full 0.397
_diffrn_reflns_Laue_measured_fraction_max 0.398
_diffrn_reflns_point_group_measured_fraction_full 0.397
_diffrn_reflns_point_group_measured_fraction_max 0.398
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             192
_reflns_number_gt                159
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.2066
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_number_reflns         192
_refine_ls_number_parameters     34
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1512P)²+1.5340P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C5 0.5416(17) 0.356(4) 0.25 0.036(4) Uiso d 1 . . C
N3 0.6767(16) 0.329(4) 0.25 0.043(4) Uiso d 1 . . N
O1 0.2726(15) 0.190(3) 0.25 0.038(3) Uiso d 1 . . O
Cu1 -0.1052(2) 0.2363(5) 0.25 0.042(4) Uani d 1 . . Cu
N1 0.0781(14) 0.352(5) 0.25 0.029(3) Uiso d 1 . . N
C1 0.054(2) 0.480(5) 0.25 0.034(4) Uiso d 1 . . C
H1 -0.055057 0.508668 0.25 0.041 Uiso calc 1 . . H
N2 0.1694(14) 0.561(4) 0.25 0.033(3) Uiso d 1 . . N
C2 0.3327(18) 0.531(4) 0.25 0.032(4) Uiso d 1 . . C
H2 0.416612 0.590279 0.25 0.038 Uiso calc 1 . . H
C3 0.3666(18) 0.399(5) 0.25 0.032(3) Uiso d 1 . . C
C4 0.2467(18) 0.307(4) 0.25 0.029(4) Uiso d 1 . . C



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C5 N3 . 1.12(2) ?
C5 C3 . 1.48(3) ?
N3 Cu1 1_655 2.01(2) ?
O1 C4 . 1.28(5) ?
Cu1 N1 . 1.93(3) ?
Cu1 N2 3_545 1.96(4) ?
Cu1 Cu1 7_566 2.9549(11) ?
Cu1 Cu1 7_565 2.9549(11) ?
N1 C1 . 1.39(5) ?
N1 C4 . 1.44(3) ?
C1 N2 . 1.27(5) ?
N2 C2 . 1.35(2) ?
C2 C3 . 1.44(6) ?
C3 C4 . 1.38(5) ?

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
N3 C5 C3 177(5) . . ?
C5 N3 Cu1 166(3) . 1_655 ?
N1 Cu1 N2 145.6(13) . 3_545 ?
N1 Cu1 N3 110.0(17) . 1_455 ?
N2 Cu1 N3 104.4(12) 3_545 1_455 ?
N1 Cu1 Cu1 86.28(16) . 7_566 ?
N2 Cu1 Cu1 95.55(19) 3_545 7_566 ?
N3 Cu1 Cu1 87.16(14) 1_455 7_566 ?
N1 Cu1 Cu1 86.28(16) . 7_565 ?
N2 Cu1 Cu1 95.55(19) 3_545 7_565 ?
N3 Cu1 Cu1 87.16(14) 1_455 7_565 ?
Cu1 Cu1 Cu1 168.5(4) 7_566 7_565 ?
C1 N1 C4 118(3) . . ?
C1 N1 Cu1 122.4(14) . . ?
C4 N1 Cu1 120(4) . . ?
N2 C1 N1 125(3) . . ?
C1 N2 C2 123(4) . . ?
C1 N2 Cu1 118(2) . 3 ?
C2 N2 Cu1 119(3) . 3 ?
N2 C2 C3 115(3) . . ?
C4 C3 C5 116(4) . . ?
C4 C3 C2 125(2) . . ?
C5 C3 C2 119(3) . . ?
O1 C4 C3 126(2) . . ?
O1 C4 N1 119(3) . . ?
C3 C4 N1 114(4) . . ?



####################################################################### 
# 
# 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_avg112_2p75_
_database_code_depnum_ccdc_archive 'CCDC 1993342'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriguez Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

_audit_creation_date             2020-03-12T08:42:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C5 H2 Cu N3 O'
_chemical_formula_weight         183.64

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_Int_Tables_number      57
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'
_cell_length_a                   7.9702(8)
_cell_length_b                   10.714(9)
_cell_length_c                   5.6247(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     480.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    563
_cell_measurement_theta_min      1.766
_cell_measurement_theta_max      17.901
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    2.539
_exptl_crystal_F_000             360
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.12418
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         2750000
_diffrn_ambient_environment      'collected in a Diamond Anvil Cell'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49276
_diffrn_source                   synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_reflns_number            1533
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_theta_min         1.771
_diffrn_reflns_theta_max         17.851
_diffrn_reflns_theta_full        17.197
_diffrn_measured_fraction_theta_max 0.399
_diffrn_measured_fraction_theta_full 0.413
_diffrn_reflns_Laue_measured_fraction_full 0.413
_diffrn_reflns_Laue_measured_fraction_max 0.399
_diffrn_reflns_point_group_measured_fraction_full 0.413
_diffrn_reflns_point_group_measured_fraction_max 0.399
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             213
_reflns_number_gt                179
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.2069
_refine_ls_goodness_of_fit_ref   1.167
_refine_ls_restrained_S_all      1.167
_refine_ls_number_reflns         213
_refine_ls_number_parameters     34
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1528P)²+0.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.814
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C5 0.5459(12) 0.363(3) 0.25 0.027(3) Uiso d 1 . . C
N3 0.6825(13) 0.331(3) 0.25 0.037(3) Uiso d 1 . . N
O1 0.2799(13) 0.191(3) 0.25 0.033(3) Uiso d 1 . . O
Cu1 -0.10157(17) 0.2340(4) 0.25 0.039(3) Uani d 1 . . Cu
N1 0.0844(11) 0.347(3) 0.25 0.024(2) Uiso d 1 . . N
C1 0.0551(16) 0.469(4) 0.25 0.027(3) Uiso d 1 . . C
H1 -0.056797 0.493149 0.25 0.032 Uiso calc 1 . . H
N2 0.1710(12) 0.561(3) 0.25 0.030(3) Uiso d 1 . . N
C2 0.3314(14) 0.525(3) 0.25 0.024(3) Uiso d 1 . . C
H2 0.415805 0.585356 0.25 0.029 Uiso calc 1 . . H
C3 0.3725(14) 0.401(3) 0.25 0.025(2) Uiso d 1 . . C
C4 0.2507(16) 0.302(4) 0.25 0.025(3) Uiso d 1 . . C



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C5 N3 . 1.139(19) ?
C5 C3 . 1.44(2) ?
N3 Cu1 1_655 2.012(19) ?
O1 C4 . 1.21(4) ?
Cu1 N1 . 1.92(2) ?
Cu1 N2 3_545 1.94(3) ?
Cu1 Cu1 7_566 2.8333(10) ?
Cu1 Cu1 7_565 2.8333(10) ?
N1 C1 . 1.32(4) ?
N1 C4 . 1.41(2) ?
C1 N2 . 1.35(4) ?
N2 C2 . 1.334(18) ?
C2 C3 . 1.37(4) ?
C3 C4 . 1.44(4) ?

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
N3 C5 C3 179(3) . . ?
C5 N3 Cu1 166(3) . 1_655 ?
N1 Cu1 N2 145.9(10) . 3_545 ?
N1 Cu1 N3 109.5(14) . 1_455 ?
N2 Cu1 N3 104.6(9) 3_545 1_455 ?
N1 Cu1 Cu1 85.60(13) . 7_566 ?
N2 Cu1 Cu1 96.67(16) 3_545 7_566 ?
N3 Cu1 Cu1 86.40(13) 1_455 7_566 ?
N1 Cu1 Cu1 85.60(13) . 7_565 ?
N2 Cu1 Cu1 96.67(16) 3_545 7_565 ?
N3 Cu1 Cu1 86.40(13) 1_455 7_565 ?
Cu1 Cu1 Cu1 166.1(3) 7_566 7_565 ?
C1 N1 C4 120(2) . . ?
C1 N1 Cu1 119.1(12) . . ?
C4 N1 Cu1 121(3) . . ?
N2 C1 N1 126.8(17) . . ?
C2 N2 C1 117(3) . . ?
C2 N2 Cu1 123(2) . 3 ?
C1 N2 Cu1 120.3(14) . 3 ?
N2 C2 C3 120(2) . . ?
C2 C3 C4 123.7(15) . . ?
C2 C3 C5 120(2) . . ?
C4 C3 C5 116(3) . . ?
O1 C4 N1 121(3) . . ?
O1 C4 C3 126.5(14) . . ?
N1 C4 C3 112(3) . . ?


####################################################################### 
# 
# 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_avg112_4p2_
_database_code_depnum_ccdc_archive 'CCDC 1993343'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriguez Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-03-28 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

_audit_creation_date             2020-03-13T10:18:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C5 H2 Cu N3 O'
_chemical_formula_weight         183.64

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_Int_Tables_number      57
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'
_cell_length_a                   7.9478(16)
_cell_length_b                   10.61(2)
_cell_length_c                   5.5058(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     464.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    257
_cell_measurement_theta_min      3.389
_cell_measurement_theta_max      16.672
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    2.627
_exptl_crystal_F_000             360
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.592
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_pressure         4200000
_diffrn_ambient_environment      'collected in a Diamond Anvil Cell'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49276
_diffrn_source                   synchrotron
_diffrn_radiation_monochromator  synchrotron
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_reflns_number            1114
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.1187
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         16.733
_diffrn_reflns_theta_full        16.733
_diffrn_measured_fraction_theta_max 0.364
_diffrn_measured_fraction_theta_full 0.364
_diffrn_reflns_Laue_measured_fraction_full 0.364
_diffrn_reflns_Laue_measured_fraction_max 0.364
_diffrn_reflns_point_group_measured_fraction_full 0.364
_diffrn_reflns_point_group_measured_fraction_max 0.364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             160
_reflns_number_gt                121
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.058
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1222
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_refine_ls_number_reflns         160
_refine_ls_number_parameters     34
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
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 0 '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 0.006 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C5 0.5496(17) 0.367(3) 0.25 0.030(3) Uiso d 1 . . C
N3 0.6876(16) 0.332(3) 0.25 0.041(3) Uiso d 1 . . N
O1 0.2831(12) 0.187(3) 0.25 0.031(3) Uiso d 1 . . O
Cu1 -0.09964(18) 0.2322(4) 0.25 0.035(3) Uani d 1 . . Cu
N1 0.0854(16) 0.350(4) 0.25 0.033(3) Uiso d 1 . . N
C1 0.058(2) 0.470(5) 0.25 0.034(4) Uiso d 1 . . C
H1 -0.053631 0.495504 0.25 0.041 Uiso calc 1 . . H
N2 0.1724(15) 0.560(3) 0.25 0.036(3) Uiso d 1 . . N
C2 0.3382(17) 0.527(3) 0.25 0.030(3) Uiso d 1 . . C
H2 0.422582 0.587602 0.25 0.036 Uiso calc 1 . . H
C3 0.3775(16) 0.397(3) 0.25 0.025(3) Uiso d 1 . . C
C4 0.2541(16) 0.303(4) 0.25 0.023(3) Uiso d 1 . . C



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C5 N3 . 1.16(2) ?
C5 C3 . 1.40(2) ?
N3 Cu1 1_655 1.996(19) ?
O1 C4 . 1.26(5) ?
Cu1 N2 3_545 1.91(3) ?
Cu1 N1 . 1.93(3) ?
Cu1 Cu1 7_566 2.7786(13) ?
Cu1 Cu1 7_565 2.7786(13) ?
N1 C1 . 1.29(5) ?
N1 C4 . 1.43(3) ?
C1 N2 . 1.32(4) ?
N2 C2 . 1.36(2) ?
C2 C3 . 1.41(4) ?
C3 C4 . 1.40(4) ?

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
N3 C5 C3 175(4) . . ?
C5 N3 Cu1 166(3) . 1_655 ?
N2 Cu1 N1 147.9(11) 3_545 . ?
N2 Cu1 N3 104.5(9) 3_545 1_455 ?
N1 Cu1 N3 107.6(14) . 1_455 ?
N2 Cu1 Cu1 97.43(17) 3_545 7_566 ?
N1 Cu1 Cu1 84.96(15) . 7_566 ?
N3 Cu1 Cu1 85.86(14) 1_455 7_566 ?
N2 Cu1 Cu1 97.43(17) 3_545 7_565 ?
N1 Cu1 Cu1 84.96(15) . 7_565 ?
N3 Cu1 Cu1 85.86(14) 1_455 7_565 ?
Cu1 Cu1 Cu1 164.4(4) 7_566 7_565 ?
C1 N1 C4 120(3) . . ?
C1 N1 Cu1 120.7(14) . . ?
C4 N1 Cu1 119(3) . . ?
N1 C1 N2 127(2) . . ?
C1 N2 C2 118(3) . . ?
C1 N2 Cu1 119.0(19) . 3 ?
C2 N2 Cu1 123(2) . 3 ?
N2 C2 C3 118(3) . . ?
C4 C3 C5 121(3) . . ?
C4 C3 C2 122.6(18) . . ?
C5 C3 C2 116(2) . . ?
O1 C4 C3 124.9(17) . . ?
O1 C4 N1 121(3) . . ?
C3 C4 N1 114(3) . . ?



