# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1981306'
loop_
_audit_author_name
_audit_author_address
'Sammer Yousuf'
;University of Karachi
Pakistan
;
_audit_update_record             
;
2020-02-01 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 N4 O5'
_chemical_formula_weight         338.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0540(2)
_cell_length_b                   21.5123(5)
_cell_length_c                   10.5167(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.1910(10)
_cell_angle_gamma                90
_cell_volume                     1586.58(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9980
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      66.56

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.901
_shelx_estimated_absorpt_T_min   0.799
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22825
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.110
_diffrn_reflns_theta_max         66.635
_diffrn_reflns_theta_full        66.635
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2806
_reflns_number_gt                2487
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0444P)²+0.7593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2806
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O1 O 0.59611(13) 0.02811(5) 0.85778(10) 0.0185(2) Uani 1 1 d . . . . .
H1 H 0.630784 -0.005255 0.825814 0.028 Uiso 1 1 calc R U . . .
O2 O 0.32193(16) 0.00610(5) 0.73953(12) 0.0313(3) Uani 1 1 d . . . . .
O3 O -0.09690(13) 0.19386(4) 0.82601(9) 0.0150(2) Uani 1 1 d . . . . .
O4 O 0.13492(14) 0.26734(4) 0.98004(9) 0.0159(2) Uani 1 1 d . . . . .
H4 H 0.022614 0.273154 0.946832 0.024 Uiso 1 1 calc R U . . .
O5 O 0.48227(13) 0.23319(4) 1.07070(9) 0.0148(2) Uani 1 1 d . . . . .
N1 N 0.00796(16) 0.13791(6) 0.26643(11) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.31829(16) 0.15870(5) 0.38741(11) 0.0143(3) Uani 1 1 d . . . . .
N3 N 0.09799(17) 0.08403(6) 0.46920(11) 0.0174(3) Uani 1 1 d . . . . .
N4 N 0.25557(16) 0.05809(5) 0.27998(11) 0.0146(3) Uani 1 1 d . . . . .
C1 C 0.4157(2) 0.03916(7) 0.81633(14) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.33878(19) 0.09763(6) 0.86740(13) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.45302(19) 0.13565(6) 0.95095(13) 0.0139(3) Uani 1 1 d . . . . .
H3 H 0.578588 0.122990 0.981885 0.017 Uiso 1 1 calc R U . . .
C4 C 0.38233(19) 0.19229(6) 0.98890(12) 0.0124(3) Uani 1 1 d . . . . .
C5 C 0.19686(19) 0.21117(6) 0.94346(12) 0.0122(3) Uani 1 1 d . . . . .
C6 C 0.08253(19) 0.17135(6) 0.86213(12) 0.0128(3) Uani 1 1 d . . . . .
C7 C 0.15279(19) 0.11499(6) 0.82347(13) 0.0148(3) Uani 1 1 d . . . . .
H7 H 0.074913 0.088477 0.767607 0.018 Uiso 1 1 calc R U . . .
C8 C -0.2131(2) 0.15781(7) 0.73281(13) 0.0160(3) Uani 1 1 d . . . . .
H8A H -0.337661 0.177920 0.713929 0.024 Uiso 1 1 calc R U . . .
H8B H -0.150459 0.154908 0.654278 0.024 Uiso 1 1 calc R U . . .
H8C H -0.230675 0.115995 0.766623 0.024 Uiso 1 1 calc R U . . .
C9 C 0.67232(19) 0.21470(7) 1.11909(13) 0.0155(3) Uani 1 1 d . . . . .
H9A H 0.730493 0.247046 1.176219 0.023 Uiso 1 1 calc R U . . .
H9B H 0.667221 0.175615 1.166480 0.023 Uiso 1 1 calc R U . . .
H9C H 0.748791 0.208830 1.047557 0.023 Uiso 1 1 calc R U . . .
C10 C 0.1551(2) 0.18469(7) 0.30323(13) 0.0162(3) Uani 1 1 d . . . . .
H10A H 0.097864 0.219240 0.348209 0.019 Uiso 1 1 calc R U . . .
H10B H 0.202090 0.201865 0.225112 0.019 Uiso 1 1 calc R U . . .
C11 C 0.2434(2) 0.13174(7) 0.50178(13) 0.0172(3) Uani 1 1 d . . . . .
H11A H 0.350246 0.113227 0.557973 0.021 Uiso 1 1 calc R U . . .
H11B H 0.187759 0.165401 0.550162 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1820(2) 0.03433(7) 0.39864(14) 0.0173(3) Uani 1 1 d . . . . .
H12A H 0.084593 0.001966 0.375507 0.021 Uiso 1 1 calc R U . . .
H12B H 0.287923 0.014909 0.454230 0.021 Uiso 1 1 calc R U . . .
C13 C 0.0931(2) 0.08726(7) 0.19921(13) 0.0164(3) Uani 1 1 d . . . . .
H13A H 0.138714 0.103600 0.119913 0.020 Uiso 1 1 calc R U . . .
H13B H -0.005095 0.055337 0.174646 0.020 Uiso 1 1 calc R U . . .
C14 C -0.0583(2) 0.11229(7) 0.38403(14) 0.0192(3) Uani 1 1 d . . . . .
H14A H -0.117174 0.145978 0.430489 0.023 Uiso 1 1 calc R U . . .
H14B H -0.157363 0.080484 0.360541 0.023 Uiso 1 1 calc R U . . .
C15 C 0.39814(19) 0.10719(7) 0.31782(14) 0.0159(3) Uani 1 1 d . . . . .
H15A H 0.506380 0.088611 0.372630 0.019 Uiso 1 1 calc R U . . .
H15B H 0.447949 0.123823 0.240174 0.019 Uiso 1 1 calc R U . . .


_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
O1 C1 1.3219(17) . ?
O1 H1 0.8400 . ?
O2 C1 1.2166(18) . ?
O3 C6 1.3701(16) . ?
O3 C8 1.4357(16) . ?
O4 C5 1.3547(16) . ?
O4 H4 0.8400 . ?
O5 C4 1.3713(16) . ?
O5 C9 1.4378(16) . ?
N1 C13 1.4627(18) . ?
N1 C10 1.4673(18) . ?
N1 C14 1.4753(19) . ?
N2 C15 1.4729(18) . ?
N2 C11 1.4831(17) . ?
N2 C10 1.4840(17) . ?
N3 C12 1.4628(18) . ?
N3 C11 1.4653(18) . ?
N3 C14 1.4747(19) . ?
N4 C15 1.4830(17) . ?
N4 C13 1.4893(17) . ?
N4 C12 1.4925(17) . ?
C1 C2 1.4924(19) . ?
C2 C3 1.392(2) . ?
C2 C7 1.394(2) . ?
C3 C4 1.3911(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.4036(19) . ?
C5 C6 1.4025(19) . ?
C6 C7 1.387(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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
C1 O1 H1 109.5 . . ?
C6 O3 C8 116.16(10) . . ?
C5 O4 H4 109.5 . . ?
C4 O5 C9 116.18(10) . . ?
C13 N1 C10 108.82(11) . . ?
C13 N1 C14 108.11(11) . . ?
C10 N1 C14 108.31(11) . . ?
C15 N2 C11 107.31(11) . . ?
C15 N2 C10 107.50(10) . . ?
C11 N2 C10 108.05(10) . . ?
C12 N3 C11 108.60(11) . . ?
C12 N3 C14 108.09(11) . . ?
C11 N3 C14 108.17(11) . . ?
C15 N4 C13 108.10(11) . . ?
C15 N4 C12 107.85(11) . . ?
C13 N4 C12 107.81(10) . . ?
O2 C1 O1 123.28(13) . . ?
O2 C1 C2 122.62(13) . . ?
O1 C1 C2 114.04(12) . . ?
C3 C2 C7 120.79(13) . . ?
C3 C2 C1 120.95(12) . . ?
C7 C2 C1 118.16(13) . . ?
C4 C3 C2 119.65(13) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O5 C4 C3 124.47(12) . . ?
O5 C4 C5 115.16(12) . . ?
C3 C4 C5 120.37(12) . . ?
O4 C5 C6 122.42(12) . . ?
O4 C5 C4 118.60(12) . . ?
C6 C5 C4 118.98(12) . . ?
O3 C6 C7 125.19(12) . . ?
O3 C6 C5 113.98(12) . . ?
C7 C6 C5 120.83(13) . . ?
C6 C7 C2 119.35(13) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 N2 112.33(11) . . ?
N1 C10 H10A 109.1 . . ?
N2 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
N2 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N3 C11 N2 112.70(11) . . ?
N3 C11 H11A 109.1 . . ?
N2 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
N2 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N3 C12 N4 111.72(11) . . ?
N3 C12 H12A 109.3 . . ?
N4 C12 H12A 109.3 . . ?
N3 C12 H12B 109.3 . . ?
N4 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
N1 C13 N4 111.66(11) . . ?
N1 C13 H13A 109.3 . . ?
N4 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
N4 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
N3 C14 N1 112.30(11) . . ?
N3 C14 H14A 109.1 . . ?
N1 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
N1 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 N4 112.62(10) . . ?
N2 C15 H15A 109.1 . . ?
N4 C15 H15A 109.1 . . ?
N2 C15 H15B 109.1 . . ?
N4 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?

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
O2 C1 C2 C3 -177.19(14) . . . . ?
O1 C1 C2 C3 0.10(19) . . . . ?
O2 C1 C2 C7 -0.8(2) . . . . ?
O1 C1 C2 C7 176.48(12) . . . . ?
C7 C2 C3 C4 -1.4(2) . . . . ?
C1 C2 C3 C4 174.85(12) . . . . ?
C9 O5 C4 C3 -0.23(18) . . . . ?
C9 O5 C4 C5 179.67(11) . . . . ?
C2 C3 C4 O5 179.92(12) . . . . ?
C2 C3 C4 C5 0.02(19) . . . . ?
O5 C4 C5 O4 1.75(17) . . . . ?
C3 C4 C5 O4 -178.34(12) . . . . ?
O5 C4 C5 C6 -178.22(11) . . . . ?
C3 C4 C5 C6 1.69(19) . . . . ?
C8 O3 C6 C7 -5.26(18) . . . . ?
C8 O3 C6 C5 174.03(11) . . . . ?
O4 C5 C6 O3 -1.35(18) . . . . ?
C4 C5 C6 O3 178.62(11) . . . . ?
O4 C5 C6 C7 177.97(12) . . . . ?
C4 C5 C6 C7 -2.06(19) . . . . ?
O3 C6 C7 C2 179.94(12) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C3 C2 C7 C6 1.1(2) . . . . ?
C1 C2 C7 C6 -175.31(12) . . . . ?
C13 N1 C10 N2 -59.25(14) . . . . ?
C14 N1 C10 N2 58.05(14) . . . . ?
C15 N2 C10 N1 58.28(14) . . . . ?
C11 N2 C10 N1 -57.25(14) . . . . ?
C12 N3 C11 N2 59.18(15) . . . . ?
C14 N3 C11 N2 -57.91(14) . . . . ?
C15 N2 C11 N3 -58.32(14) . . . . ?
C10 N2 C11 N3 57.33(14) . . . . ?
C11 N3 C12 N4 -58.49(14) . . . . ?
C14 N3 C12 N4 58.64(14) . . . . ?
C15 N4 C12 N3 57.89(14) . . . . ?
C13 N4 C12 N3 -58.61(14) . . . . ?
C10 N1 C13 N4 58.54(14) . . . . ?
C14 N1 C13 N4 -58.90(14) . . . . ?
C15 N4 C13 N1 -57.64(14) . . . . ?
C12 N4 C13 N1 58.69(14) . . . . ?
C12 N3 C14 N1 -59.04(14) . . . . ?
C11 N3 C14 N1 58.37(14) . . . . ?
C13 N1 C14 N3 59.17(14) . . . . ?
C10 N1 C14 N3 -58.59(14) . . . . ?
C11 N2 C15 N4 58.08(14) . . . . ?
C10 N2 C15 N4 -57.93(14) . . . . ?
C13 N4 C15 N2 58.00(14) . . . . ?
C12 N4 C15 N2 -58.31(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N4 0.84 1.83 2.6380(15) 159.6 3_656 yes
O4 H4 O3 0.84 2.24 2.6880(13) 113.8 . yes
O4 H4 N2 0.84 2.10 2.8284(15) 144.4 4_566 yes
C8 H8C O1 0.98 2.50 3.4212(17) 156.9 1_455 yes
C9 H9B N1 0.98 2.64 3.1535(18) 112.6 1_656 yes
C11 H11B O5 0.99 2.64 3.5565(18) 153.8 4_565 yes
C14 H14A O4 0.99 2.65 3.5887(17) 159.1 4_565 yes
C14 H14B O2 0.99 2.38 3.3335(18) 161.6 3_556 yes

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1981308'
loop_
_audit_author_name
_audit_author_address
'Sammer Yousuf'
;University of Karachi
Pakistan
;
_audit_update_record             
;
2020-02-01 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O2'
_chemical_formula_weight         218.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'

_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+1/2'
'-x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   30.5126(10)
_cell_length_b                   9.6815(3)
_cell_length_c                   7.3786(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2179.70(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8348
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      68.31

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14765
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.792
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2034
_reflns_number_gt                1948
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0359P)²+0.4840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 849 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2034
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
O2 O 0.39774(4) 0.84492(14) -0.15804(19) 0.0214(3) Uani 1 1 d . . . . .
O1 O 0.40590(5) 0.62853(13) -0.0562(2) 0.0279(3) Uani 1 1 d . . . . .
N2 N 0.500000 0.6077(2) 0.4257(3) 0.0177(5) Uani 1 2 d S T P . .
N1 N 0.45990(5) 0.77561(14) 0.6093(2) 0.0165(3) Uani 1 1 d . . . . .
N3 N 0.500000 0.8530(2) 0.3408(3) 0.0183(5) Uani 1 2 d S T P . .
C3 C 0.35787(6) 0.70635(17) 0.2591(3) 0.0169(4) Uani 1 1 d . . . . .
H3 H 0.370853 0.617282 0.253061 0.020 Uiso 1 1 calc R U . . .
C4 C 0.33249(6) 0.73836(18) 0.4233(2) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.39112(6) 0.74483(18) -0.0389(3) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.500000 0.7960(3) 0.7184(3) 0.0172(5) Uani 1 2 d S T P . .
H10A H 0.500000 0.890697 0.769201 0.021 Uiso 1 2 calc R U P . .
H10B H 0.500000 0.730077 0.820954 0.021 Uiso 1 2 calc R U P . .
C8 C 0.30035(6) 0.66036(19) 0.7043(3) 0.0229(4) Uani 1 1 d . . . . .
H8 H 0.296629 0.590025 0.792716 0.028 Uiso 1 1 calc R U . . .
C11 C 0.500000 0.7079(3) 0.2754(4) 0.0212(6) Uani 1 2 d S T P . .
H11A H 0.473772 0.692368 0.199120 0.025 Uiso 0.5 1 calc R U P . .
H11B H 0.526228 0.692368 0.199120 0.025 Uiso 0.5 1 calc R U P . .
C12 C 0.46108(6) 0.87294(18) 0.4544(3) 0.0183(4) Uani 1 1 d . . . . .
H12A H 0.434472 0.859832 0.379576 0.022 Uiso 1 1 calc R U . . .
H12B H 0.460820 0.968840 0.500960 0.022 Uiso 1 1 calc R U . . .
C9 C 0.32635(6) 0.63580(18) 0.5534(2) 0.0193(4) Uani 1 1 d . . . . .
H9 H 0.340065 0.548428 0.538724 0.023 Uiso 1 1 calc R U . . .
C5 C 0.31262(6) 0.86696(18) 0.4494(3) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.317321 0.938949 0.364084 0.023 Uiso 1 1 calc R U . . .
C6 C 0.28609(6) 0.89009(19) 0.5989(3) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.272172 0.977113 0.613911 0.026 Uiso 1 1 calc R U . . .
C13 C 0.46098(6) 0.63170(17) 0.5372(3) 0.0183(4) Uani 1 1 d . . . . .
H13A H 0.460794 0.565660 0.639658 0.022 Uiso 1 1 calc R U . . .
H13B H 0.434397 0.614907 0.463524 0.022 Uiso 1 1 calc R U . . .
C7 C 0.27975(6) 0.7868(2) 0.7268(3) 0.0234(4) Uani 1 1 d . . . . .
H7 H 0.261455 0.802705 0.828872 0.028 Uiso 1 1 calc R U . . .
C2 C 0.36448(6) 0.78946(18) 0.1180(2) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.351857 0.879163 0.118166 0.022 Uiso 1 1 calc R U . . .
H14 H 0.4185(10) 0.811(3) -0.256(4) 0.056(9) Uiso 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
O2 C1 1.324(2) . ?
O2 H14 1.02(3) . ?
O1 C1 1.220(2) . ?
N2 C13 1.466(2) 3_655 ?
N2 C13 1.466(2) . ?
N2 C11 1.473(3) . ?
N1 C10 1.478(2) . ?
N1 C12 1.482(2) . ?
N1 C13 1.492(2) . ?
N3 C12 1.466(2) 3_655 ?
N3 C12 1.466(2) . ?
N3 C11 1.485(3) . ?
C3 C2 1.331(3) . ?
C3 C4 1.471(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.394(3) . ?
C4 C5 1.398(2) . ?
C1 C2 1.479(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C8 C7 1.386(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C9 H9 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C7 H7 0.9500 . ?
C2 H2 0.9500 . ?

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
C1 O2 H14 109.1(17) . . ?
C13 N2 C13 108.6(2) 3_655 . ?
C13 N2 C11 108.57(12) 3_655 . ?
C13 N2 C11 108.57(12) . . ?
C10 N1 C12 108.36(15) . . ?
C10 N1 C13 107.51(15) . . ?
C12 N1 C13 108.58(14) . . ?
C12 N3 C12 108.2(2) 3_655 . ?
C12 N3 C11 108.07(13) 3_655 . ?
C12 N3 C11 108.07(13) . . ?
C2 C3 C4 126.62(16) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C9 C4 C5 118.78(17) . . ?
C9 C4 C3 119.21(16) . . ?
C5 C4 C3 121.94(17) . . ?
O1 C1 O2 123.37(18) . . ?
O1 C1 C2 123.68(17) . . ?
O2 C1 C2 112.94(15) . . ?
N1 C10 N1 111.7(2) 3_655 . ?
N1 C10 H10A 109.3 3_655 . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 3_655 . ?
N1 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C7 C8 C9 120.46(19) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
N2 C11 N3 112.2(2) . . ?
N2 C11 H11A 109.2 . . ?
N3 C11 H11A 109.2 . . ?
N2 C11 H11B 109.2 . . ?
N3 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 N1 112.14(15) . . ?
N3 C12 H12A 109.2 . . ?
N1 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
N1 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C8 C9 C4 120.48(17) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C6 C5 C4 120.42(18) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.39(17) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N2 C13 N1 111.46(14) . . ?
N2 C13 H13A 109.3 . . ?
N1 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
N1 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C8 C7 C6 119.42(19) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C3 C2 C1 121.25(16) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?

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
C2 C3 C4 C9 175.73(18) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C12 N1 C10 N1 -57.6(2) . . . 3_655 ?
C13 N1 C10 N1 59.6(2) . . . 3_655 ?
C13 N2 C11 N3 -58.96(12) 3_655 . . . ?
C13 N2 C11 N3 58.96(12) . . . . ?
C12 N3 C11 N2 58.42(13) 3_655 . . . ?
C12 N3 C11 N2 -58.42(13) . . . . ?
C12 N3 C12 N1 -58.9(2) 3_655 . . . ?
C11 N3 C12 N1 57.9(2) . . . . ?
C10 N1 C12 N3 58.5(2) . . . . ?
C13 N1 C12 N3 -58.04(19) . . . . ?
C7 C8 C9 C4 0.6(3) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C8 -176.04(17) . . . . ?
C9 C4 C5 C6 -2.2(3) . . . . ?
C3 C4 C5 C6 174.90(16) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C13 N2 C13 N1 59.6(2) 3_655 . . . ?
C11 N2 C13 N1 -58.3(2) . . . . ?
C10 N1 C13 N2 -59.1(2) . . . . ?
C12 N1 C13 N2 57.90(19) . . . . ?
C9 C8 C7 C6 -1.4(3) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C4 C3 C2 C1 179.48(17) . . . . ?
O1 C1 C2 C3 5.4(3) . . . . ?
O2 C1 C2 C3 -173.82(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10A N3 0.99 2.54 3.516(3) 169.8 2_675 yes
C13 H13B O1 0.99 2.52 3.106(2) 118.0 4_565 yes
O2 H14 N1 1.02(3) 1.64(3) 2.645(2) 168(3) 1_554 yes

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1981307'
loop_
_audit_author_name
_audit_author_address
'Sammer Yousuf'
;University of Karachi
Pakistan
;
_audit_update_record             
;
2020-02-01 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 F3 N4 O2'
_chemical_formula_weight         394.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.3306(13)
_cell_length_b                   5.9128(5)
_cell_length_c                   17.5030(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.156(3)
_cell_angle_gamma                90
_cell_volume                     1792.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9845
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      68.44

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.008
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41634
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.057
_diffrn_reflns_theta_max         68.490
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3285
_reflns_number_gt                2821
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0461P)²+0.8448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3285
_refine_ls_number_parameters     309
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.010
_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
O2 O 0.34562(5) 0.06423(17) 0.88673(5) 0.0179(2) Uani 1 1 d . . . . .
O1 O 0.11351(5) -0.56295(17) 0.92805(5) 0.0181(2) Uani 1 1 d . . . . .
H1 H 0.124126 -0.644762 0.966246 0.027 Uiso 1 1 calc R U . . .
N1 N 0.18236(7) 0.2952(2) 0.69667(6) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.12984(6) 0.2920(2) 0.56469(6) 0.0144(2) Uani 1 1 d . . . . .
C2 C 0.24754(8) -0.4540(2) 0.94588(7) 0.0153(3) Uani 1 1 d . . . . .
H2 H 0.259374 -0.590552 0.972405 0.018 Uiso 1 1 calc R U . . .
C7 C 0.36726(7) 0.1100(2) 0.81367(7) 0.0145(3) Uani 1 1 d . . . . .
C18 C 0.05316(8) 0.2401(2) 0.59513(7) 0.0171(3) Uani 1 1 d . . . . .
H18A H 0.012458 0.299908 0.559437 0.020 Uiso 1 1 calc R U . . .
H18B H 0.046744 0.073919 0.597817 0.020 Uiso 1 1 calc R U . . .
N3 N 0.04293(6) 0.3370(2) 0.67139(6) 0.0147(2) Uani 1 1 d . . . . .
C10 C 0.41359(7) 0.2279(2) 0.66943(7) 0.0161(3) Uani 1 1 d . . . . .
C12 C 0.40522(8) 0.3132(2) 0.80309(8) 0.0169(3) Uani 1 1 d . . . . .
H12 H 0.415429 0.411254 0.845263 0.020 Uiso 1 1 calc R U . . .
C4 C 0.28775(8) -0.0981(2) 0.89562(7) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.17243(8) -0.4137(2) 0.91788(7) 0.0132(3) Uani 1 1 d . . . . .
N4 N 0.13112(7) 0.6427(2) 0.63888(7) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.15567(7) -0.2144(2) 0.87803(7) 0.0140(3) Uani 1 1 d . . . . .
H6 H 0.104672 -0.186725 0.858446 0.017 Uiso 1 1 calc R U . . .
C13 C 0.43499(8) 0.2979(3) 0.59098(8) 0.0215(3) Uani 1 1 d . . . . .
C8 C 0.35469(8) -0.0394(2) 0.75308(7) 0.0156(3) Uani 1 1 d . . . . .
H8 H 0.330556 -0.181263 0.761063 0.019 Uiso 1 1 calc R U . . .
C15 C 0.13876(8) 0.5400(2) 0.56332(8) 0.0183(3) Uani 1 1 d . . . . .
H15A H 0.190154 0.577961 0.544036 0.022 Uiso 1 1 calc R U . . .
H15B H 0.099200 0.605227 0.527462 0.022 Uiso 1 1 calc R U . . .
C3 C 0.30518(8) -0.2948(2) 0.93510(7) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.356225 -0.321258 0.954767 0.019 Uiso 1 1 calc R U . . .
C5 C 0.21341(8) -0.0563(2) 0.86695(7) 0.0149(3) Uani 1 1 d . . . . .
H5 H 0.202081 0.079677 0.839885 0.018 Uiso 1 1 calc R U . . .
C17 C 0.10439(8) 0.2442(3) 0.72288(7) 0.0183(3) Uani 1 1 d . . . . .
H17A H 0.098963 0.307867 0.774712 0.022 Uiso 1 1 calc R U . . .
H17B H 0.098039 0.078144 0.726353 0.022 Uiso 1 1 calc R U . . .
C11 C 0.42823(8) 0.3730(2) 0.73099(8) 0.0175(3) Uani 1 1 d . . . . .
H11 H 0.453955 0.512715 0.723492 0.021 Uiso 1 1 calc R U . . .
C14 C 0.18917(8) 0.2000(2) 0.61988(7) 0.0168(3) Uani 1 1 d . . . . .
H14A H 0.183709 0.033576 0.622474 0.020 Uiso 1 1 calc R U . . .
H14B H 0.241164 0.234104 0.601329 0.020 Uiso 1 1 calc R U . . .
C9 C 0.37782(8) 0.0211(2) 0.68083(8) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.369154 -0.079272 0.639008 0.020 Uiso 1 1 calc R U . . .
C16 C 0.05449(8) 0.5827(2) 0.66682(8) 0.0200(3) Uani 1 1 d . . . . .
H16A H 0.048737 0.649654 0.718143 0.024 Uiso 1 1 calc R U . . .
H16B H 0.014044 0.648571 0.632110 0.024 Uiso 1 1 calc R U . . .
C19 C 0.19006(8) 0.5413(3) 0.69106(8) 0.0224(3) Uani 1 1 d . . . . .
H19A H 0.241940 0.578203 0.672771 0.027 Uiso 1 1 calc R U . . .
H19B H 0.185757 0.608384 0.742539 0.027 Uiso 1 1 calc R U . . .
F1 F 0.5102(5) 0.309(3) 0.5845(5) 0.063(5) Uani 0.5 1 d . U P A 1
F2 F 0.4091(8) 0.1560(17) 0.5365(3) 0.046(3) Uani 0.5 1 d . U P A 1
F3 F 0.4041(13) 0.496(2) 0.5726(6) 0.053(4) Uani 0.33 1 d . U P A 1
F1A F 0.4968(11) 0.185(4) 0.5683(10) 0.048(3) Uani 0.25 1 d . U P A 2
F2A F 0.4467(19) 0.127(3) 0.5421(10) 0.060(6) Uani 0.25 1 d . U P A 2
F3A F 0.3788(7) 0.424(4) 0.5574(7) 0.049(4) Uani 0.33 1 d . U P A 2
F1B F 0.4927(10) 0.423(4) 0.5852(6) 0.044(5) Uani 0.25 1 d . U P A 3
F2B F 0.3820(7) 0.274(5) 0.5411(4) 0.037(3) Uani 0.25 1 d . U P A 3
F3B F 0.4517(14) 0.5257(15) 0.5867(6) 0.060(3) Uani 0.34 1 d . U P A 3


_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
O2 C7 1.3731(16) . ?
O2 C4 1.4011(16) . ?
O1 C1 1.3665(16) . ?
O1 H1 0.8400 . ?
N1 C19 1.465(2) . ?
N1 C14 1.4658(17) . ?
N1 C17 1.4744(18) . ?
N2 C15 1.4753(18) . ?
N2 C18 1.4822(17) . ?
N2 C14 1.4869(16) . ?
C2 C3 1.390(2) . ?
C2 C1 1.3941(19) . ?
C2 H2 0.9500 . ?
C7 C12 1.385(2) . ?
C7 C8 1.3912(19) . ?
C18 N3 1.4694(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N3 C16 1.4693(19) . ?
N3 C17 1.4750(17) . ?
C10 C9 1.389(2) . ?
C10 C11 1.393(2) . ?
C10 C13 1.4941(18) . ?
C12 C11 1.3837(19) . ?
C12 H12 0.9500 . ?
C4 C3 1.3807(19) . ?
C4 C5 1.3870(19) . ?
C1 C6 1.3943(19) . ?
N4 C15 1.4657(18) . ?
N4 C19 1.472(2) . ?
N4 C16 1.4755(18) . ?
C6 C5 1.3882(19) . ?
C6 H6 0.9500 . ?
C13 F2B 1.251(6) . ?
C13 F1B 1.252(13) . ?
C13 F1 1.313(8) . ?
C13 F3 1.325(9) . ?
C13 F1A 1.334(9) . ?
C13 F2 1.335(6) . ?
C13 F2A 1.344(14) . ?
C13 F3A 1.345(9) . ?
C13 F3B 1.380(9) . ?
C8 C9 1.3879(19) . ?
C8 H8 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C11 H11 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C9 H9 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
F1A F2A 1.027(13) . ?
F1B F3B 0.936(13) . ?

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
C7 O2 C4 117.39(10) . . ?
C1 O1 H1 109.5 . . ?
C19 N1 C14 108.00(11) . . ?
C19 N1 C17 108.11(11) . . ?
C14 N1 C17 108.25(11) . . ?
C15 N2 C18 107.92(11) . . ?
C15 N2 C14 107.68(11) . . ?
C18 N2 C14 107.35(10) . . ?
C3 C2 C1 120.17(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C7 C12 116.30(12) . . ?
O2 C7 C8 122.99(12) . . ?
C12 C7 C8 120.68(12) . . ?
N3 C18 N2 112.72(11) . . ?
N3 C18 H18A 109.0 . . ?
N2 C18 H18A 109.0 . . ?
N3 C18 H18B 109.0 . . ?
N2 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C16 N3 C18 108.36(10) . . ?
C16 N3 C17 107.72(11) . . ?
C18 N3 C17 107.50(10) . . ?
C9 C10 C11 120.03(12) . . ?
C9 C10 C13 120.22(12) . . ?
C11 C10 C13 119.74(13) . . ?
C11 C12 C7 119.88(13) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C3 C4 C5 120.93(13) . . ?
C3 C4 O2 119.24(12) . . ?
C5 C4 O2 119.80(12) . . ?
O1 C1 C2 122.42(12) . . ?
O1 C1 C6 117.93(12) . . ?
C2 C1 C6 119.65(13) . . ?
C15 N4 C19 107.87(11) . . ?
C15 N4 C16 108.22(11) . . ?
C19 N4 C16 107.98(11) . . ?
C5 C6 C1 120.07(12) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
F2B C13 F1B 125.4(5) . . ?
F1 C13 F3 109.1(5) . . ?
F1 C13 F2 106.2(4) . . ?
F3 C13 F2 105.1(5) . . ?
F1A C13 F2A 45.1(5) . . ?
F1A C13 F3A 136.3(6) . . ?
F2A C13 F3A 105.3(8) . . ?
F2B C13 F3B 102.9(6) . . ?
F1B C13 F3B 41.3(6) . . ?
F2B C13 C10 114.1(3) . . ?
F1B C13 C10 117.7(5) . . ?
F1 C13 C10 112.0(4) . . ?
F3 C13 C10 110.9(4) . . ?
F1A C13 C10 111.5(4) . . ?
F2 C13 C10 113.2(3) . . ?
F2A C13 C10 115.1(6) . . ?
F3A C13 C10 110.8(4) . . ?
F3B C13 C10 112.3(3) . . ?
C9 C8 C7 119.25(13) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N4 C15 N2 112.57(11) . . ?
N4 C15 H15A 109.1 . . ?
N2 C15 H15A 109.1 . . ?
N4 C15 H15B 109.1 . . ?
N2 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C4 C3 C2 119.56(12) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C4 C5 C6 119.62(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C17 N3 112.52(10) . . ?
N1 C17 H17A 109.1 . . ?
N3 C17 H17A 109.1 . . ?
N1 C17 H17B 109.1 . . ?
N3 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C12 C11 C10 119.84(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
N1 C14 N2 112.20(11) . . ?
N1 C14 H14A 109.2 . . ?
N2 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
N2 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C8 C9 C10 120.25(13) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N3 C16 N4 112.45(11) . . ?
N3 C16 H16A 109.1 . . ?
N4 C16 H16A 109.1 . . ?
N3 C16 H16B 109.1 . . ?
N4 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N1 C19 N4 112.54(11) . . ?
N1 C19 H19A 109.1 . . ?
N4 C19 H19A 109.1 . . ?
N1 C19 H19B 109.1 . . ?
N4 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
F2A F1A C13 68.0(9) . . ?
F1A F2A C13 66.9(9) . . ?
F3B F1B C13 76.7(7) . . ?
F1B F3B C13 62.0(8) . . ?

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
C4 O2 C7 C12 160.53(12) . . . . ?
C4 O2 C7 C8 -21.46(18) . . . . ?
C15 N2 C18 N3 -57.19(14) . . . . ?
C14 N2 C18 N3 58.62(14) . . . . ?
N2 C18 N3 C16 57.38(14) . . . . ?
N2 C18 N3 C17 -58.77(14) . . . . ?
O2 C7 C12 C11 -179.33(12) . . . . ?
C8 C7 C12 C11 2.6(2) . . . . ?
C7 O2 C4 C3 116.46(13) . . . . ?
C7 O2 C4 C5 -65.61(16) . . . . ?
C3 C2 C1 O1 -178.92(11) . . . . ?
C3 C2 C1 C6 0.93(19) . . . . ?
O1 C1 C6 C5 179.31(11) . . . . ?
C2 C1 C6 C5 -0.55(18) . . . . ?
C9 C10 C13 F2B 48.2(15) . . . . ?
C11 C10 C13 F2B -130.5(15) . . . . ?
C9 C10 C13 F1B -149.8(14) . . . . ?
C11 C10 C13 F1B 31.5(14) . . . . ?
C9 C10 C13 F1 -113.4(10) . . . . ?
C11 C10 C13 F1 67.9(10) . . . . ?
C9 C10 C13 F3 124.5(11) . . . . ?
C11 C10 C13 F3 -54.2(11) . . . . ?
C9 C10 C13 F1A -74.7(15) . . . . ?
C11 C10 C13 F1A 106.6(15) . . . . ?
C9 C10 C13 F2 6.6(8) . . . . ?
C11 C10 C13 F2 -172.1(8) . . . . ?
C9 C10 C13 F2A -25.5(16) . . . . ?
C11 C10 C13 F2A 155.8(16) . . . . ?
C9 C10 C13 F3A 93.8(12) . . . . ?
C11 C10 C13 F3A -84.9(12) . . . . ?
C9 C10 C13 F3B 164.8(11) . . . . ?
C11 C10 C13 F3B -13.9(12) . . . . ?
O2 C7 C8 C9 179.46(12) . . . . ?
C12 C7 C8 C9 -2.6(2) . . . . ?
C19 N4 C15 N2 58.26(14) . . . . ?
C16 N4 C15 N2 -58.33(15) . . . . ?
C18 N2 C15 N4 57.71(14) . . . . ?
C14 N2 C15 N4 -57.89(14) . . . . ?
C5 C4 C3 C2 0.40(19) . . . . ?
O2 C4 C3 C2 178.31(11) . . . . ?
C1 C2 C3 C4 -0.85(19) . . . . ?
C3 C4 C5 C6 -0.02(19) . . . . ?
O2 C4 C5 C6 -177.92(11) . . . . ?
C1 C6 C5 C4 0.10(19) . . . . ?
C19 N1 C17 N3 58.10(14) . . . . ?
C14 N1 C17 N3 -58.67(15) . . . . ?
C16 N3 C17 N1 -58.17(14) . . . . ?
C18 N3 C17 N1 58.41(15) . . . . ?
C7 C12 C11 C10 -0.4(2) . . . . ?
C9 C10 C11 C12 -1.7(2) . . . . ?
C13 C10 C11 C12 176.99(13) . . . . ?
C19 N1 C14 N2 -58.44(14) . . . . ?
C17 N1 C14 N2 58.39(14) . . . . ?
C15 N2 C14 N1 57.87(14) . . . . ?
C18 N2 C14 N1 -58.10(14) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C11 C10 C9 C8 1.7(2) . . . . ?
C13 C10 C9 C8 -177.00(13) . . . . ?
C18 N3 C16 N4 -57.71(14) . . . . ?
C17 N3 C16 N4 58.31(14) . . . . ?
C15 N4 C16 N3 58.19(15) . . . . ?
C19 N4 C16 N3 -58.33(14) . . . . ?
C14 N1 C19 N4 58.95(14) . . . . ?
C17 N1 C19 N4 -57.97(14) . . . . ?
C15 N4 C19 N1 -58.68(14) . . . . ?
C16 N4 C19 N1 58.07(15) . . . . ?
F3A C13 F1A F2A -59.7(14) . . . . ?
C10 C13 F1A F2A 104.6(10) . . . . ?
F3A C13 F2A F1A 141.8(9) . . . . ?
C10 C13 F2A F1A -95.9(8) . . . . ?
F2B C13 F1B F3B 66.7(11) . . . . ?
C10 C13 F1B F3B -93.0(6) . . . . ?
F2B C13 F3B F1B -129.8(9) . . . . ?
C10 C13 F3B F1B 107.0(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N2 0.84 1.93 2.7538(14) 166.6 4_556
C2 H2 F2B 0.95 2.63 3.389(12) 136.7 4_556
C6 H6 N3 0.95 2.60 3.5302(17) 168.1 2_546
C3 H3 F1 0.95 2.56 3.289(9) 133.8 2_646
C3 H3 F2 0.95 2.59 3.273(6) 129.1 4_556
C3 H3 F1A 0.95 2.59 3.436(18) 147.9 2_646
C14 H14A N4 0.99 2.50 3.4653(19) 163.4 1_545

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.046

