# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1562594'
_audit_update_record             
;
2017-07-17 deposited with the CCDC.
2017-07-25 downloaded from the CCDC.
;
_audit_creation_date             2017-07-12
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.07.04 svn.r3433 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H4 Cu F N3 O2, C2 H6 O'
_chemical_formula_sum            'C9 H10 Cu F N3 O3'
_chemical_formula_weight         290.74
_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'
F F 0.0171 0.0103 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.592(2)
_cell_length_b                   6.3812(18)
_cell_length_c                   23.954(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.070(4)
_cell_angle_gamma                90
_cell_volume                     1156.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.4291
_cell_measurement_theta_min      2.7525
_shelx_estimated_absorpt_T_max   0.714
_shelx_estimated_absorpt_T_min   0.691
_exptl_absorpt_coefficient_mu    1.902
_exptl_absorpt_correction_T_max  0.7139
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7688
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.753
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  bruker-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                1399
_reflns_number_total             2029
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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         -0.365
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.034
_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)+(0.0444P)²+0.0691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0873
_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 planarity
 C5, C7, C6, F1B
 with sigma of 0.1
3. Uiso/Uaniso restraints and constraints
Uanis(F1B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.008
4. Rigid body (RIGU) restrains
 C4, C3, C5, C6, F1B, C7, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H4)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(H6)=FVAR(1)
6.a Riding coordinates:
 O3(H3A)
6.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
6.c Me refined with riding coordinates:
 C9(H9A,H9B,H9C)
6.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_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
F1A F 0.3206(6) 0.6196(5) -0.01219(14) 0.0834(15) Uani 0.821(6) 1 d . . P A 1
Cu1 Cu 0.75276(6) 0.68380(6) 0.24834(2) 0.02230(16) Uani 1 1 d . . . . .
O1 O 0.5985(3) 0.7571(4) 0.18140(10) 0.0293(6) Uani 1 1 d . . . . .
O2 O 0.5880(3) 1.1082(4) 0.18661(10) 0.0305(7) Uani 1 1 d . . . . .
O3 O 0.9223(3) 0.4314(4) 0.19740(11) 0.0319(6) Uani 1 1 d . . . . .
H3A H 1.0360 0.4378 0.2125 0.048 Uiso 1 1 d R . . . .
C1 C 0.5521(4) 0.9354(6) 0.16319(14) 0.0237(8) Uani 1 1 d . . . . .
C2 C 0.4414(4) 0.9424(6) 0.10784(14) 0.0248(8) Uani 1 1 d . U . . .
C3 C 0.4307(5) 0.7695(6) 0.07320(16) 0.0356(10) Uani 1 1 d . U . . .
H3 H 0.4881 0.6456 0.0843 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3343(6) 0.7830(7) 0.02212(17) 0.0462(11) Uani 1 1 d . U . . .
H4 H 0.3294 0.6674 -0.0016 0.055 Uiso 0.179(6) 1 calc R . P A 2
C5 C 0.2443(6) 0.9629(8) 0.00494(18) 0.0479(11) Uani 1 1 d . U . . .
H5 H 0.1784 0.9696 -0.0296 0.057 Uiso 1 1 calc R . . . .
C6 C 0.2552(6) 1.1293(8) 0.0400(2) 0.0547(13) Uani 1 1 d . U . . .
H6 H 0.1945 1.2513 0.0292 0.066 Uiso 0.821(6) 1 calc R . P A 1
C7 C 0.3527(6) 1.1243(6) 0.09111(18) 0.0408(11) Uani 1 1 d . U . . .
H7 H 0.3590 1.2418 0.1142 0.049 Uiso 1 1 calc R . . . .
C8 C 0.9059(6) 0.4179(7) 0.13718(18) 0.0512(12) Uani 1 1 d . . . . .
H8A H 0.7820 0.4034 0.1240 0.061 Uiso 1 1 calc R . . . .
H8B H 0.9674 0.2938 0.1258 0.061 Uiso 1 1 calc R . . . .
C9 C 0.9798(7) 0.6056(8) 0.1107(2) 0.0743(17) Uani 1 1 d . . . . .
H9A H 0.9663 0.5904 0.0706 0.111 Uiso 1 1 calc R . . . .
H9B H 0.9178 0.7286 0.1212 0.111 Uiso 1 1 calc R . . . .
H9C H 1.1031 0.6190 0.1231 0.111 Uiso 1 1 calc R . . . .
N1 N 0.5996(4) 0.4382(4) 0.26195(12) 0.0234(7) Uani 1 1 d . . . . .
N2 N 0.4432(4) 0.4385(5) 0.24725(15) 0.0361(8) Uani 1 1 d . . . . .
N3 N 0.2954(5) 0.4386(7) 0.2343(2) 0.0846(17) Uani 1 1 d . . . . .
F1B F 0.150(2) 1.279(2) 0.0258(7) 0.072(5) Uani 0.179(6) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C4 1.326(5) . ?
Cu1 O1 1.957(2) . ?
Cu1 O2 1.947(2) 2_645 ?
Cu1 N1 1.995(3) . ?
Cu1 N1 2.000(3) 2_655 ?
O1 C1 1.258(4) . ?
O2 Cu1 1.947(2) 2_655 ?
O2 C1 1.256(4) . ?
O3 C8 1.439(5) . ?
C1 C2 1.507(5) . ?
C2 C3 1.378(5) . ?
C2 C7 1.383(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.380(6) . ?
C5 C6 1.352(6) . ?
C6 C7 1.373(6) . ?
C6 F1B 1.270(15) . ?
C8 C9 1.489(6) . ?
N1 Cu1 2.000(3) 2_645 ?
N1 N2 1.209(4) . ?
N2 N3 1.137(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
O1 Cu1 N1 90.35(11) . 2_655 ?
O1 Cu1 N1 90.38(11) . . ?
O2 Cu1 O1 178.17(11) 2_645 . ?
O2 Cu1 N1 90.23(11) 2_645 . ?
O2 Cu1 N1 89.12(11) 2_645 2_655 ?
N1 Cu1 N1 176.88(8) . 2_655 ?
C1 O1 Cu1 129.0(2) . . ?
C1 O2 Cu1 132.1(2) . 2_655 ?
O1 C1 C2 116.7(3) . . ?
O2 C1 O1 126.6(3) . . ?
O2 C1 C2 116.7(3) . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 C7 119.7(4) . . ?
C7 C2 C1 120.0(4) . . ?
C4 C3 C2 119.0(4) . . ?
F1A C4 C3 120.7(4) . . ?
F1A C4 C5 117.4(4) . . ?
C3 C4 C5 121.9(4) . . ?
C6 C5 C4 117.8(4) . . ?
C5 C6 C7 122.3(4) . . ?
F1B C6 C5 114.8(8) . . ?
F1B C6 C7 122.2(9) . . ?
C6 C7 C2 119.2(4) . . ?
O3 C8 C9 112.1(4) . . ?
Cu1 N1 Cu1 106.06(13) . 2_645 ?
N2 N1 Cu1 120.8(3) . 2_645 ?
N2 N1 Cu1 121.5(3) . . ?
N3 N2 N1 178.9(5) . . ?

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
F1A C4 C5 C6 179.0(5) . . . . ?
Cu1 O1 C1 O2 -4.6(6) . . . . ?
Cu1 O1 C1 C2 175.8(2) . . . . ?
Cu1 O2 C1 O1 9.5(6) 2_655 . . . ?
Cu1 O2 C1 C2 -170.9(2) 2_655 . . . ?
O1 C1 C2 C3 -15.8(5) . . . . ?
O1 C1 C2 C7 165.5(3) . . . . ?
O2 C1 C2 C3 164.6(3) . . . . ?
O2 C1 C2 C7 -14.1(5) . . . . ?
C1 C2 C3 C4 -177.6(4) . . . . ?
C1 C2 C7 C6 178.7(4) . . . . ?
C2 C3 C4 F1A -179.7(4) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
C3 C2 C7 C6 0.0(6) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C4 C5 C6 F1B -170.3(10) . . . . ?
C5 C6 C7 C2 -0.9(7) . . . . ?
C7 C2 C3 C4 1.1(6) . . . . ?
F1B C6 C7 C2 169.3(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
