# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1870700'
loop_
_audit_author_name
_audit_author_address
'Junbiao Wu'
;Northeastern University
China
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 F Ga N2 O8'
_chemical_formula_weight         422.96

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'
Ga Ga 0.2307 1.6083 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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.
;

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

_cell_length_a                   18.4449(10)
_cell_length_b                   10.4561(5)
_cell_length_c                   3.8127(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.617(2)
_cell_angle_gamma                90
_cell_volume                     733.86(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4958
_cell_measurement_theta_min      7.701
_cell_measurement_theta_max      54.868

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.104
_exptl_absorpt_coefficient_mu    1.940
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6477
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5805
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         3.850
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             882
_reflns_number_gt                880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+2.0179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         882
_refine_ls_number_parameters     67
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.000
_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_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
Ga1 Ga 0.5000 0.5000 0.0000 0.01637(15) Uani 1 4 d S T P . .
O2 O 0.30680(10) 0.6307(2) 0.1255(7) 0.0562(6) Uani 1 1 d . . . . .
O3 O 0.42304(9) 0.62491(16) -0.0016(5) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.36244(12) 0.5740(2) 0.0656(6) 0.0303(5) Uani 1 1 d . . . . .
C4 C 0.07610(15) 0.3879(3) 0.4224(11) 0.0617(10) Uani 1 1 d . . . . .
H4A H 0.0527 0.3100 0.4501 0.074 Uiso 1 1 calc R U . . .
C3 C 0.14818(16) 0.3904(3) 0.3426(11) 0.0653(11) Uani 1 1 d . . . . .
H3A H 0.1732 0.3142 0.3138 0.078 Uiso 1 1 calc R U . . .
N1 N 0.18121(15) 0.5000 0.3078(9) 0.0394(7) Uani 1 2 d S T P . .
C1 C 0.03911(15) 0.5000 0.4604(8) 0.0243(6) Uani 1 2 d S T P . .
F1 F 0.5000 0.5000 0.5000 0.0722(14) Uani 1 4 d S TU P . .
H1N H 0.2225 0.5000 0.2611 0.087 Uiso 1 2 d R U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ga1 0.0140(2) 0.0208(2) 0.0147(2) 0.000 0.00396(14) 0.000
O2 0.0274(9) 0.0388(11) 0.1055(18) 0.0110(11) 0.0284(10) 0.0101(8)
O3 0.0227(8) 0.0246(8) 0.0650(12) 0.0107(8) 0.0168(8) 0.0038(7)
C2 0.0214(10) 0.0299(13) 0.0406(13) 0.0065(10) 0.0093(9) 0.0038(9)
C4 0.0298(14) 0.0284(14) 0.130(3) -0.0197(17) 0.0332(17) -0.0033(11)
C3 0.0309(14) 0.0430(17) 0.125(3) -0.0221(19) 0.0313(17) 0.0041(13)
N1 0.0181(13) 0.056(2) 0.0454(18) 0.000 0.0124(12) 0.000
C1 0.0185(14) 0.0282(16) 0.0268(15) 0.000 0.0074(11) 0.000
F1 0.0405(19) 0.160(4) 0.0164(15) 0.000 0.0053(13) 0.000

_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
Ga1 F1 1.90635(10) 1_554 ?
Ga1 F1 1.90635(10) . ?
Ga1 O3 1.9287(16) . ?
Ga1 O3 1.9288(16) 6_565 ?
Ga1 O3 1.9288(16) 2_655 ?
Ga1 O3 1.9288(16) 5_665 ?
O2 C2 1.219(3) . ?
O3 C2 1.279(3) . ?
C2 C2 1.547(5) 6_565 ?
C4 C1 1.369(3) . ?
C4 C3 1.383(4) . ?
C4 H4A 0.9300 . ?
C3 N1 1.309(4) . ?
C3 H3A 0.9300 . ?
N1 C3 1.309(4) 6_565 ?
N1 H1N 0.7927 . ?
C1 C4 1.369(3) 6_565 ?
C1 C1 1.492(6) 5_566 ?
F1 Ga1 1.90635(10) 1_556 ?

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
F1 Ga1 F1 180.0 1_554 . ?
F1 Ga1 O3 92.48(6) 1_554 . ?
F1 Ga1 O3 87.52(6) . . ?
F1 Ga1 O3 92.48(6) 1_554 6_565 ?
F1 Ga1 O3 87.52(6) . 6_565 ?
O3 Ga1 O3 85.25(10) . 6_565 ?
F1 Ga1 O3 87.52(6) 1_554 2_655 ?
F1 Ga1 O3 92.48(6) . 2_655 ?
O3 Ga1 O3 94.75(10) . 2_655 ?
O3 Ga1 O3 180.0 6_565 2_655 ?
F1 Ga1 O3 87.52(6) 1_554 5_665 ?
F1 Ga1 O3 92.48(6) . 5_665 ?
O3 Ga1 O3 180.0 . 5_665 ?
O3 Ga1 O3 94.75(10) 6_565 5_665 ?
O3 Ga1 O3 85.25(10) 2_655 5_665 ?
C2 O3 Ga1 111.71(15) . . ?
O2 C2 O3 126.3(2) . . ?
O2 C2 C2 119.10(15) . 6_565 ?
O3 C2 C2 114.62(13) . 6_565 ?
C1 C4 C3 120.0(3) . . ?
C1 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
N1 C3 C4 119.9(3) . . ?
N1 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C3 N1 C3 122.3(3) . 6_565 ?
C3 N1 H1N 118.9 . . ?
C3 N1 H1N 118.9 6_565 . ?
C4 C1 C4 117.9(3) 6_565 . ?
C4 C1 C1 121.07(15) 6_565 5_566 ?
C4 C1 C1 121.07(15) . 5_566 ?
Ga1 F1 Ga1 180.0 1_556 . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.071

_shelx_res_file                  
;

    d.res created by SHELXL-2014/7


TITL d in P2(1)                       New: C2/m
CELL  0.71073   18.4449   10.4561    3.8127    90.000    93.617    90.000
ZERR        2    0.0010    0.0005    0.0002     0.000     0.002     0.000
LATT   7
SYMM             - X ,              Y ,            - Z
SFAC  C  H Ga  N  O  F
UNIT    28 20 2 4 16 2

L.S. 5
FMAP 2
PLAN -20
ACTA
isor 0.02 o1
BOND $H

WGHT    0.019800    2.017900
FVAR       0.24895   0.20000
GA1   3    0.500000    0.500000    0.000000    10.25000    0.01402    0.02075 =
         0.01472    0.00000    0.00396    0.00000
O2    5    0.306799    0.630672    0.125479    11.00000    0.02738    0.03884 =
         0.10549    0.01103    0.02843    0.01015
O3    5    0.423038    0.624913   -0.001602    11.00000    0.02267    0.02462 =
         0.06497    0.01073    0.01675    0.00381
C2    1    0.362436    0.573975    0.065641    11.00000    0.02143    0.02988 =
         0.04063    0.00653    0.00929    0.00384
C4    1    0.076095    0.387869    0.422374    11.00000    0.02976    0.02843 =
         0.13037   -0.01970    0.03323   -0.00333
AFIX  43
H4A   2    0.052748    0.310026    0.450136    11.00000   -1.20000
AFIX   0
C3    1    0.148180    0.390366    0.342649    11.00000    0.03092    0.04299 =
         0.12532   -0.02206    0.03131    0.00412
AFIX  43
H3A   2    0.173172    0.314219    0.313836    11.00000   -1.20000
AFIX   0
N1    4    0.181208    0.500000    0.307770    10.50000    0.01808    0.05608 =
         0.04545    0.00000    0.01240    0.00000
C1    1    0.039110    0.500000    0.460424    10.50000    0.01851    0.02820 =
         0.02680    0.00000    0.00737    0.00000
F1    6    0.500000    0.500000    0.500000    10.25000    0.04055    0.16027 =
         0.01638    0.00000    0.00534    0.00000
AFIX   3
H1N   2    0.222480    0.500000    0.261064    10.50000   -1.20000
AFIX   0
HKLF 4

REM  d in P2(1)                       New: C2/m
REM R1 =  0.0268 for     880 Fo > 4sig(Fo)  and  0.0269 for all     882 data
REM     67 parameters refined using      6 restraints

END

WGHT      0.0196      2.0244

REM Highest difference peak  0.397,  deepest hole -0.401,  1-sigma level  0.071
Q1    1   0.5000  0.5505 -0.5000  10.50000  0.05    0.40
Q2    1   0.5835  0.9049  0.5662  11.00000  0.05    0.32
Q3    1   0.3698  0.5000  0.0872  10.50000  0.05    0.29
Q4    1   0.2924  0.5957 -0.0527  11.00000  0.05    0.29
Q5    1   0.5618  0.9313  0.3222  11.00000  0.05    0.28
Q6    1   0.6105  0.8995  0.4967  11.00000  0.05    0.27
Q7    1   0.4374  0.5000  0.0746  10.50000  0.05    0.26
Q8    1   0.5426  0.8230  0.2303  11.00000  0.05    0.24
Q9    1   0.6436  0.9315  0.2272  11.00000  0.05    0.23
Q10   1   0.5817  0.5862  0.1366  11.00000  0.05    0.23
Q11   1   0.6496  0.9121  0.5100  11.00000  0.05    0.21
Q12   1   0.4603  0.4168  0.0587  11.00000  0.05    0.20
Q13   1   0.5675  0.8004  0.6522  11.00000  0.05    0.20
Q14   1   0.5771  0.6628 -0.0005  11.00000  0.05    0.20
Q15   1   0.4169  0.4043  0.1817  11.00000  0.05    0.19
Q16   1   0.3386  0.5000  0.3765  10.50000  0.05    0.19
Q17   1   0.6196  1.0000  0.6262  10.50000  0.05    0.18
Q18   1   0.4416  0.3827  0.1734  11.00000  0.05    0.17
Q19   1   0.2718  0.5000  0.0060  10.50000  0.05    0.17
Q20   1   0.1763  0.3313  0.1234  11.00000  0.05    0.17
;
_shelx_res_checksum              58137
