# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_gres_0m
_database_code_depnum_ccdc_archive 'CCDC 1889411'
loop_
_audit_author_name
_audit_author_address
'Parimaladevi Palanisamy'
;Indian Institute of Technology, Gandhinagar
India
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2019-01-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C6 H6 O2, H2 O'
_chemical_formula_sum            'C28 H33 Cl F N4 O6'
_chemical_formula_weight         576.03
_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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1014(11)
_cell_length_b                   11.2699(15)
_cell_length_c                   15.485(2)
_cell_angle_alpha                90.087(5)
_cell_angle_beta                 99.656(5)
_cell_angle_gamma                101.285(5)
_cell_volume                     1366.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6108
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0859 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.9087. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17432
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.238
_diffrn_ambient_temperature      150.53
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5134
_reflns_number_total             6751
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.323
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6751
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+0.4327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1069
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C3(H3A), C6(H6), C7(H7), C10(H10), C11(H11), C14(H14), C2A(H2AA),
 C4A(H4A), C5A(H5A), C6A(H6A)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O2A(H2A)
;
_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
Cl1 Cl 0.76585(6) 0.84652(4) 0.67986(3) 0.03245(12) Uani 1 1 d . . . . .
F1 F 0.78075(13) 1.06875(9) 0.78223(7) 0.0334(3) Uani 1 1 d . . . . .
O1 O 0.16952(15) 0.19166(10) 0.88192(7) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.01729(15) 0.14733(10) 1.01264(7) 0.0239(3) Uani 1 1 d . . . . .
O3 O 0.26368(18) -0.20033(12) 0.50678(8) 0.0353(3) Uani 1 1 d . . . . .
N1 N 0.19104(17) 0.56274(12) 1.11984(8) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.34783(17) 0.70910(12) 1.03608(8) 0.0207(3) Uani 1 1 d . . . . .
N3 N 0.41154(17) 0.65503(12) 0.90151(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H 0.392511 0.595624 0.861928 0.025 Uiso 1 1 calc R . . . .
N4 N 0.20826(17) -0.00817(12) 0.61167(8) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.17970(19) 0.28977(14) 0.93513(10) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.09555(19) 0.26427(14) 1.00929(10) 0.0186(3) Uani 1 1 d . . . . .
C3 C 0.10054(19) 0.35514(14) 1.06918(10) 0.0186(3) Uani 1 1 d . . . . .
H3A H 0.045911 0.338033 1.118721 0.022 Uiso 1 1 calc R . . . .
C4 C 0.18683(19) 0.47436(14) 1.05743(10) 0.0173(3) Uani 1 1 d . . . . .
C5 C 0.26422(19) 0.50033(14) 0.98332(10) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.26064(19) 0.40504(14) 0.92270(10) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.315018 0.421547 0.873025 0.022 Uiso 1 1 calc R . . . .
C7 C 0.2713(2) 0.67172(15) 1.10493(10) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.276090 0.732390 1.148451 0.026 Uiso 1 1 calc R . . . .
C8 C 0.34271(19) 0.62450(14) 0.97495(10) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.50745(19) 0.76428(14) 0.87755(10) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.5358(2) 0.87544(14) 0.92245(11) 0.0225(3) Uani 1 1 d . . . . .
H10 H 0.492258 0.881414 0.975208 0.027 Uiso 1 1 calc R . . . .
C11 C 0.6281(2) 0.97767(15) 0.88994(11) 0.0247(4) Uani 1 1 d . . . . .
H11 H 0.645821 1.053952 0.919849 0.030 Uiso 1 1 calc R . . . .
C12 C 0.6938(2) 0.96837(14) 0.81447(11) 0.0221(3) Uani 1 1 d . . . . .
C13 C 0.67248(19) 0.85785(15) 0.77138(10) 0.0201(3) Uani 1 1 d . . . . .
C14 C 0.57867(19) 0.75594(14) 0.80215(10) 0.0198(3) Uani 1 1 d . . . . .
H14 H 0.562501 0.679973 0.771994 0.024 Uiso 1 1 calc R . . . .
C15 C 0.2345(2) 0.21292(14) 0.80145(10) 0.0232(3) Uani 1 1 d . . . . .
H15A H 0.358072 0.248987 0.813602 0.028 Uiso 1 1 calc R . . . .
H15B H 0.174214 0.269089 0.765501 0.028 Uiso 1 1 calc R . . . .
C16 C -0.0727(2) 0.11485(15) 1.08371(11) 0.0236(3) Uani 1 1 d . . . . .
H16A H -0.119837 0.027646 1.079715 0.035 Uiso 1 1 calc GR . . . .
H16B H -0.165931 0.159332 1.080746 0.035 Uiso 1 1 calc GR . . . .
H16C H 0.005916 0.135288 1.139412 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.2042(2) 0.09140(14) 0.75380(10) 0.0234(3) Uani 1 1 d . . . . .
H17A H 0.080442 0.055956 0.743204 0.028 Uiso 1 1 calc R . . . .
H17B H 0.263606 0.035971 0.791068 0.028 Uiso 1 1 calc R . . . .
C18 C 0.2682(2) 0.10245(14) 0.66687(10) 0.0229(3) Uani 1 1 d . . . . .
H18A H 0.228737 0.170721 0.635166 0.027 Uiso 1 1 calc R . . . .
H18B H 0.394693 0.120928 0.678128 0.027 Uiso 1 1 calc R . . . .
C19 C 0.2515(3) 0.01056(17) 0.52470(11) 0.0365(5) Uani 1 1 d . . . . .
H19A H 0.376845 0.036294 0.529620 0.044 Uiso 1 1 calc R . . . .
H19B H 0.197847 0.075946 0.496964 0.044 Uiso 1 1 calc R . . . .
C20 C 0.1914(3) -0.10327(19) 0.46808(12) 0.0437(5) Uani 1 1 d . . . . .
H20A H 0.065213 -0.125949 0.459854 0.052 Uiso 1 1 calc R . . . .
H20B H 0.224333 -0.088443 0.409711 0.052 Uiso 1 1 calc R . . . .
C21 C 0.2228(3) -0.22054(17) 0.59214(13) 0.0417(5) Uani 1 1 d . . . . .
H21A H 0.276855 -0.286336 0.618831 0.050 Uiso 1 1 calc R . . . .
H21B H 0.097512 -0.246456 0.587666 0.050 Uiso 1 1 calc R . . . .
C22 C 0.2837(3) -0.10769(16) 0.64975(11) 0.0322(4) Uani 1 1 d . . . . .
H22A H 0.252174 -0.123725 0.708311 0.039 Uiso 1 1 calc R . . . .
H22B H 0.409723 -0.084633 0.657264 0.039 Uiso 1 1 calc R . . . .
O1A O 0.68792(16) 0.35294(12) 0.61333(8) 0.0327(3) Uani 1 1 d . . . . .
H1A H 0.697836 0.309361 0.571183 0.049 Uiso 1 1 calc GR . . . .
O2A O 0.27919(14) 0.51824(11) 0.72959(7) 0.0249(3) Uani 1 1 d . . . . .
H2A H 0.172601 0.510335 0.723853 0.037 Uiso 1 1 calc GR . . . .
C1A C 0.5282(2) 0.37972(15) 0.59977(11) 0.0233(3) Uani 1 1 d . . . . .
C2A C 0.4803(2) 0.43481(15) 0.66912(10) 0.0227(3) Uani 1 1 d . . . . .
H2AA H 0.557141 0.452703 0.723088 0.027 Uiso 1 1 calc R . . . .
C3A C 0.3196(2) 0.46366(14) 0.65928(10) 0.0216(3) Uani 1 1 d . . . . .
C4A C 0.2071(2) 0.43836(16) 0.57996(11) 0.0256(4) Uani 1 1 d . . . . .
H4A H 0.096724 0.457691 0.573000 0.031 Uiso 1 1 calc R . . . .
C5A C 0.2592(2) 0.38440(16) 0.51132(11) 0.0278(4) Uani 1 1 d . . . . .
H5A H 0.183455 0.367738 0.456922 0.033 Uiso 1 1 calc R . . . .
C6A C 0.4183(2) 0.35429(15) 0.52003(11) 0.0263(4) Uani 1 1 d . . . . .
H6A H 0.451869 0.317004 0.472524 0.032 Uiso 1 1 calc R . . . .
O1S O -0.04710(16) 0.49914(13) 0.72929(8) 0.0374(3) Uani 1 1 d . . . . .
H1SA H -0.076147 0.476144 0.779180 0.056 Uiso 1 1 d G . . . .
H1SB H -0.118712 0.457336 0.686712 0.056 Uiso 1 1 d G . . . .


_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
Cl1 C13 1.7303(15) . ?
F1 C12 1.3539(18) . ?
O1 C1 1.3590(18) . ?
O1 C15 1.4349(18) . ?
O2 C2 1.3512(18) . ?
O2 C16 1.4293(18) . ?
O3 C20 1.426(2) . ?
O3 C21 1.424(2) . ?
N1 C4 1.3785(19) . ?
N1 C7 1.313(2) . ?
N2 C7 1.349(2) . ?
N2 C8 1.3324(19) . ?
N3 C8 1.3644(19) . ?
N3 C9 1.4074(19) . ?
N4 C18 1.463(2) . ?
N4 C19 1.453(2) . ?
N4 C22 1.459(2) . ?
C1 C2 1.433(2) . ?
C1 C6 1.365(2) . ?
C2 C3 1.371(2) . ?
C3 C4 1.415(2) . ?
C4 C5 1.402(2) . ?
C5 C6 1.418(2) . ?
C5 C8 1.435(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.375(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.380(2) . ?
C15 C17 1.512(2) . ?
C17 C18 1.518(2) . ?
C19 C20 1.503(3) . ?
C21 C22 1.503(3) . ?
O1A C1A 1.368(2) . ?
O2A C3A 1.3666(18) . ?
C1A C2A 1.386(2) . ?
C1A C6A 1.389(2) . ?
C2A C3A 1.387(2) . ?
C3A C4A 1.394(2) . ?
C4A C5A 1.388(2) . ?
C5A C6A 1.381(2) . ?

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 C15 117.15(12) . . ?
C2 O2 C16 117.57(12) . . ?
C21 O3 C20 110.41(14) . . ?
C7 N1 C4 115.60(13) . . ?
C8 N2 C7 116.11(14) . . ?
C8 N3 C9 131.70(13) . . ?
C19 N4 C18 110.99(13) . . ?
C19 N4 C22 108.27(13) . . ?
C22 N4 C18 111.29(13) . . ?
O1 C1 C2 114.30(13) . . ?
O1 C1 C6 125.59(14) . . ?
C6 C1 C2 120.12(14) . . ?
O2 C2 C1 114.06(13) . . ?
O2 C2 C3 126.04(14) . . ?
C3 C2 C1 119.90(14) . . ?
C2 C3 C4 120.19(14) . . ?
N1 C4 C3 118.38(13) . . ?
N1 C4 C5 121.64(14) . . ?
C5 C4 C3 119.98(14) . . ?
C4 C5 C6 119.19(14) . . ?
C4 C5 C8 116.17(13) . . ?
C6 C5 C8 124.64(14) . . ?
C1 C6 C5 120.56(14) . . ?
N1 C7 N2 128.67(14) . . ?
N2 C8 N3 120.10(14) . . ?
N2 C8 C5 121.75(14) . . ?
N3 C8 C5 118.15(13) . . ?
C10 C9 N3 125.61(14) . . ?
C10 C9 C14 119.38(14) . . ?
C14 C9 N3 115.00(14) . . ?
C11 C10 C9 119.84(14) . . ?
C12 C11 C10 119.97(15) . . ?
F1 C12 C11 119.66(15) . . ?
F1 C12 C13 119.63(14) . . ?
C11 C12 C13 120.71(15) . . ?
C12 C13 Cl1 120.06(12) . . ?
C12 C13 C14 119.89(14) . . ?
C14 C13 Cl1 120.05(12) . . ?
C13 C14 C9 120.13(15) . . ?
O1 C15 C17 106.79(12) . . ?
C15 C17 C18 111.64(13) . . ?
N4 C18 C17 112.33(13) . . ?
N4 C19 C20 111.11(16) . . ?
O3 C20 C19 111.05(16) . . ?
O3 C21 C22 111.04(16) . . ?
N4 C22 C21 110.90(16) . . ?
O1A C1A C2A 117.08(15) . . ?
O1A C1A C6A 121.94(14) . . ?
C2A C1A C6A 120.97(16) . . ?
C1A C2A C3A 119.63(15) . . ?
O2A C3A C2A 117.23(14) . . ?
O2A C3A C4A 122.44(15) . . ?
C2A C3A C4A 120.32(15) . . ?
C5A C4A C3A 118.79(16) . . ?
C6A C5A C4A 121.74(16) . . ?
C5A C6A C1A 118.54(15) . . ?

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
O1A H1A O3 0.84 1.83 2.6589(16) 170.7 2_656 yes
O2A H2A O1S 0.84 1.78 2.6090(17) 171.2 . yes
O1S H1SA N1 0.87 1.96 2.8116(18) 166.5 2_567 yes
O1S H1SB O1A 0.87 1.95 2.8038(18) 166.2 1_455 yes

_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_gsalt_0m
_database_code_depnum_ccdc_archive 'CCDC 1889412'
loop_
_audit_author_name
_audit_author_address
'Parimaladevi Palanisamy'
;Indian Institute of Technology, Gandhinagar
India
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2019-01-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H23 Cl F N4 O3), 2(C6 H8 O2), 2(H2 O)'
_chemical_formula_sum            'C56 H66 Cl2 F2 N8 O12'
_chemical_formula_weight         1152.06
_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'
Cl Cl 0.1484 0.1585 '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                   10.930(2)
_cell_length_b                   7.2541(14)
_cell_length_c                   35.222(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.749(7)
_cell_angle_gamma                90
_cell_volume                     2786.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5556
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.945
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1360 before and 0.0795 after correction. The Ratio of minimum to maximum transmission is 0.8253. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            transparant
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1212
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0999
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            36316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4091
_reflns_number_total             6931
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.448
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6931
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0976P)²+2.1071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2222
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C2B(H2BA), C3(H3A), C3B(H3B), C4B(H4B), C5B(H5B), C6(H6), C7(H7),
 C10(H10), C11(H11), C14(H14), C21(H21)
2.d Idealised Me refined as rotating group:
 C1B(H1BA,H1BB,H1BC), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2B(H2B)
;
_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
Cl1 Cl 0.96701(9) 0.52623(14) 0.65738(3) 0.0420(3) Uani 1 1 d . . . . .
F1 F 1.15343(17) 0.4800(3) 0.60206(6) 0.0383(5) Uani 1 1 d . . . . .
O1 O 0.2345(2) 0.0565(3) 0.55526(6) 0.0272(5) Uani 1 1 d . . . . .
O1B O 0.4623(3) 0.5348(4) 0.35581(8) 0.0640(10) Uani 1 1 d . . . . .
O2 O 0.1365(2) 0.0803(3) 0.48797(6) 0.0275(5) Uani 1 1 d . . . . .
O2B O 0.4098(3) 0.2561(4) 0.37377(7) 0.0416(6) Uani 1 1 d . . . . .
H2B H 0.441824 0.293697 0.394672 0.062 Uiso 1 1 calc GR . . . .
O3 O 0.3831(3) 0.2416(5) 0.73910(8) 0.0603(9) Uani 1 1 d . . . . .
N1 N 0.5085(2) 0.3191(4) 0.44085(7) 0.0260(6) Uani 1 1 d . . . . .
N2 N 0.6834(2) 0.3725(3) 0.48295(7) 0.0264(6) Uani 1 1 d . . . . .
N3 N 0.6832(2) 0.3011(4) 0.54697(7) 0.0256(6) Uani 1 1 d . . . . .
H3 H 0.640298 0.257162 0.565234 0.031 Uiso 1 1 calc R . . . .
N4 N 0.3061(3) 0.0214(4) 0.67509(8) 0.0312(6) Uani 1 1 d . . . . .
C1 C 0.3096(3) 0.1243(4) 0.52932(8) 0.0235(6) Uani 1 1 d . . . . .
C1B C 0.3614(4) 0.4499(6) 0.17053(11) 0.0468(10) Uani 1 1 d . . . . .
H1BA H 0.325034 0.558821 0.157773 0.070 Uiso 1 1 calc GR . . . .
H1BB H 0.303724 0.346573 0.167828 0.070 Uiso 1 1 calc GR . . . .
H1BC H 0.437541 0.417314 0.158923 0.070 Uiso 1 1 calc GR . . . .
C2 C 0.2556(3) 0.1358(4) 0.49162(9) 0.0229(6) Uani 1 1 d . . . . .
C2B C 0.3883(4) 0.4907(6) 0.21137(10) 0.0410(9) Uani 1 1 d . . . . .
H2BA H 0.437622 0.595941 0.217377 0.049 Uiso 1 1 calc R . . . .
C3 C 0.3214(3) 0.1982(4) 0.46260(9) 0.0249(7) Uani 1 1 d . . . . .
H3A H 0.285066 0.203604 0.437372 0.030 Uiso 1 1 calc R . . . .
C3B C 0.3504(3) 0.3949(5) 0.24037(10) 0.0386(8) Uani 1 1 d . . . . .
H3B H 0.297801 0.292645 0.235020 0.046 Uiso 1 1 calc R . . . .
C4 C 0.4439(3) 0.2547(4) 0.47048(8) 0.0236(7) Uani 1 1 d . . . . .
C4B C 0.3846(3) 0.4373(5) 0.27955(10) 0.0370(8) Uani 1 1 d . . . . .
H4B H 0.425077 0.551726 0.284164 0.044 Uiso 1 1 calc R . . . .
C5 C 0.4983(3) 0.2451(4) 0.50738(8) 0.0222(6) Uani 1 1 d . . . . .
C5B C 0.3664(3) 0.3359(5) 0.30997(10) 0.0388(9) Uani 1 1 d . . . . .
H5B H 0.318668 0.226907 0.306777 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4294(3) 0.1783(4) 0.53707(9) 0.0230(6) Uani 1 1 d . . . . .
H6 H 0.465632 0.170560 0.562281 0.028 Uiso 1 1 calc R . . . .
C6B C 0.4165(3) 0.3842(5) 0.34836(10) 0.0345(8) Uani 1 1 d . . . . .
C7 C 0.6224(3) 0.3742(4) 0.44910(9) 0.0281(7) Uani 1 1 d . . . . .
H7 H 0.665476 0.420094 0.428511 0.034 Uiso 1 1 calc R . . . .
C8 C 0.6244(3) 0.3063(4) 0.51231(9) 0.0234(6) Uani 1 1 d . . . . .
C9 C 0.8051(3) 0.3564(4) 0.55839(9) 0.0244(7) Uani 1 1 d . . . . .
C10 C 0.9034(3) 0.3496(4) 0.53499(9) 0.0284(7) Uani 1 1 d . . . . .
H10 H 0.890264 0.315337 0.509006 0.034 Uiso 1 1 calc R . . . .
C11 C 1.0202(3) 0.3930(4) 0.54997(10) 0.0300(7) Uani 1 1 d . . . . .
H11 H 1.087586 0.388779 0.534264 0.036 Uiso 1 1 calc R . . . .
C12 C 1.0383(3) 0.4420(4) 0.58736(10) 0.0287(7) Uani 1 1 d . . . . .
C13 C 0.9410(3) 0.4548(4) 0.61060(9) 0.0278(7) Uani 1 1 d . . . . .
C14 C 0.8241(3) 0.4112(4) 0.59600(9) 0.0254(7) Uani 1 1 d . . . . .
H14 H 0.756862 0.418845 0.611730 0.030 Uiso 1 1 calc R . . . .
C15 C 0.2836(3) 0.0375(4) 0.59391(8) 0.0257(7) Uani 1 1 d . . . . .
H15A H 0.307546 0.159338 0.604672 0.031 Uiso 1 1 calc R . . . .
H15B H 0.356733 -0.043411 0.595174 0.031 Uiso 1 1 calc R . . . .
C16 C 0.0725(3) 0.1002(5) 0.45144(9) 0.0306(7) Uani 1 1 d . . . . .
H16A H 0.112472 0.024642 0.432784 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.073761 0.229788 0.443643 0.046 Uiso 1 1 calc GR . . . .
H16C H -0.012625 0.059623 0.452871 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.1827(3) -0.0469(5) 0.61568(9) 0.0324(8) Uani 1 1 d . . . . .
H17A H 0.145130 -0.150682 0.600836 0.039 Uiso 1 1 calc R . . . .
H17B H 0.118200 0.046454 0.618989 0.039 Uiso 1 1 calc R . . . .
C18 C 0.2314(3) -0.1165(5) 0.65449(9) 0.0343(8) Uani 1 1 d . . . . .
H18A H 0.161524 -0.150353 0.669622 0.041 Uiso 1 1 calc R . . . .
H18B H 0.281074 -0.228736 0.651184 0.041 Uiso 1 1 calc R . . . .
C19 C 0.2349(3) 0.1794(5) 0.68666(10) 0.0401(9) Uani 1 1 d . . . . .
H19A H 0.173086 0.138712 0.704205 0.048 Uiso 1 1 calc R . . . .
H19B H 0.191238 0.235897 0.664048 0.048 Uiso 1 1 calc R . . . .
C20 C 0.3196(4) 0.3192(6) 0.70624(11) 0.0502(11) Uani 1 1 d . . . . .
H20A H 0.379666 0.362157 0.688335 0.060 Uiso 1 1 calc R . . . .
H20B H 0.271356 0.427146 0.713804 0.060 Uiso 1 1 calc R . . . .
C21 C 0.4504(4) 0.0843(7) 0.72867(13) 0.0581(12) Uani 1 1 d . . . . .
H21 H 0.536472 0.070726 0.733538 0.070 Uiso 1 1 calc R . . . .
C22 C 0.3693(4) -0.0580(6) 0.70906(10) 0.0432(9) Uani 1 1 d . . . . .
H22A H 0.419335 -0.164664 0.701826 0.052 Uiso 1 1 calc R . . . .
H22B H 0.308473 -0.102249 0.726584 0.052 Uiso 1 1 calc R . . . .
O1S O 0.4016(3) 0.8685(4) 0.38527(7) 0.0436(7) Uani 1 1 d . . . . .
H1SA H 0.437205 0.784480 0.372324 0.065 Uiso 1 1 d G . . . .
H1SB H 0.412427 0.970331 0.372914 0.065 Uiso 1 1 d G . . . .


_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
Cl1 C13 1.733(3) . ?
F1 C12 1.358(4) . ?
O1 C1 1.359(4) . ?
O1 C15 1.437(4) . ?
O1B C6B 1.223(4) . ?
O2 C2 1.361(4) . ?
O2 C16 1.431(4) . ?
O2B C6B 1.296(4) . ?
O3 C20 1.426(5) . ?
O3 C21 1.420(6) . ?
N1 C4 1.379(4) . ?
N1 C7 1.322(4) . ?
N2 C7 1.327(4) . ?
N2 C8 1.343(4) . ?
N3 C8 1.343(4) . ?
N3 C9 1.424(4) . ?
N4 C18 1.455(4) . ?
N4 C19 1.458(5) . ?
N4 C22 1.461(5) . ?
C1 C2 1.420(4) . ?
C1 C6 1.377(4) . ?
C1B C2B 1.479(5) . ?
C2 C3 1.365(4) . ?
C2B C3B 1.324(5) . ?
C3 C4 1.410(4) . ?
C3B C4B 1.439(5) . ?
C4 C5 1.395(4) . ?
C4B C5B 1.325(5) . ?
C5 C6 1.414(4) . ?
C5 C8 1.447(4) . ?
C5B C6B 1.468(5) . ?
C9 C10 1.398(4) . ?
C9 C14 1.386(4) . ?
C10 C11 1.386(5) . ?
C11 C12 1.366(5) . ?
C12 C13 1.387(5) . ?
C13 C14 1.383(4) . ?
C15 C17 1.514(4) . ?
C17 C18 1.520(5) . ?
C19 C20 1.509(5) . ?
C21 C22 1.499(6) . ?

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 C15 117.8(2) . . ?
C2 O2 C16 117.6(2) . . ?
C21 O3 C20 109.9(3) . . ?
C7 N1 C4 117.2(3) . . ?
C7 N2 C8 117.2(3) . . ?
C8 N3 C9 129.2(3) . . ?
C18 N4 C19 112.8(3) . . ?
C18 N4 C22 110.9(3) . . ?
C19 N4 C22 108.3(3) . . ?
O1 C1 C2 114.7(3) . . ?
O1 C1 C6 125.3(3) . . ?
C6 C1 C2 120.0(3) . . ?
O2 C2 C1 114.0(3) . . ?
O2 C2 C3 125.1(3) . . ?
C3 C2 C1 120.9(3) . . ?
C3B C2B C1B 126.3(4) . . ?
C2 C3 C4 119.2(3) . . ?
C2B C3B C4B 123.6(4) . . ?
N1 C4 C3 118.4(3) . . ?
N1 C4 C5 120.9(3) . . ?
C5 C4 C3 120.7(3) . . ?
C5B C4B C3B 127.9(4) . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 C8 116.2(3) . . ?
C6 C5 C8 124.4(3) . . ?
C4B C5B C6B 123.1(4) . . ?
C1 C6 C5 119.8(3) . . ?
O1B C6B O2B 122.2(3) . . ?
O1B C6B C5B 122.3(3) . . ?
O2B C6B C5B 115.5(3) . . ?
N1 C7 N2 127.2(3) . . ?
N2 C8 C5 121.2(3) . . ?
N3 C8 N2 119.0(3) . . ?
N3 C8 C5 119.7(3) . . ?
C10 C9 N3 124.4(3) . . ?
C14 C9 N3 115.5(3) . . ?
C14 C9 C10 120.1(3) . . ?
C11 C10 C9 119.5(3) . . ?
C12 C11 C10 119.9(3) . . ?
F1 C12 C11 119.5(3) . . ?
F1 C12 C13 119.3(3) . . ?
C11 C12 C13 121.2(3) . . ?
C12 C13 Cl1 119.8(3) . . ?
C14 C13 Cl1 120.8(2) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C9 119.9(3) . . ?
O1 C15 C17 106.2(2) . . ?
C15 C17 C18 111.5(3) . . ?
N4 C18 C17 111.8(3) . . ?
N4 C19 C20 109.5(3) . . ?
O3 C20 C19 110.9(3) . . ?
O3 C21 C22 111.8(4) . . ?
N4 C22 C21 109.9(3) . . ?

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
O2B H2B N1 0.84 1.75 2.573(4) 167.0 . yes
N3 H3 O1S 0.88 2.05 2.891(4) 160.7 3_666 yes
O1S H1SA O1B 0.87 1.93 2.733(4) 153.6 . yes
O1S H1SB O2B 0.87 2.07 2.843(4) 147.1 1_565 yes

_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_gclt_0m
_database_code_depnum_ccdc_archive 'CCDC 1889429'
loop_
_audit_author_name
_audit_author_address
'Parimaladevi Palanisamy'
;Indian Institute of Technology, Gandhinagar
India
;
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2018-12-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C9 H8 O2'
_chemical_formula_sum            'C31 H32 Cl F N4 O5'
_chemical_formula_weight         595.05
_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'
Cl Cl 0.1484 0.1585 '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                   12.1642(18)
_cell_length_b                   7.4425(11)
_cell_length_c                   31.958(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.245(6)
_cell_angle_gamma                90
_cell_volume                     2881.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1073 before and 0.0717 after correction. The Ratio of minimum to maximum transmission is 0.9021. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            transparant
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.104
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            37675
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      149.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5551
_reflns_number_total             7131
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.387
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         7131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C1A(H1A), C2A(H2AA), C3(H3A), C3A(H3AA), C4A(H4A), C6(H6), C6A(H6A),
 C7(H7), C7A(H7A), C8A(H8A), C10(H10), C11(H11), C14(H14)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.82448(4) 1.11100(6) 0.35703(2) 0.04023(14) Uani 1 1 d . . . . .
F1 F 1.00991(8) 1.01434(14) 0.41808(4) 0.0432(3) Uani 1 1 d . . . . .
O1A O 0.50847(9) 0.24633(16) 0.62229(4) 0.0339(3) Uani 1 1 d . . . . .
O2A O 0.45191(10) 0.50943(16) 0.64711(4) 0.0358(3) Uani 1 1 d . . . . .
H2A H 0.469943 0.547549 0.623964 0.054 Uiso 1 1 calc GR . . . .
O003 O 0.12215(8) 0.58545(14) 0.51457(3) 0.0251(2) Uani 1 1 d . . . . .
O004 O 0.18138(8) 0.64903(15) 0.44125(3) 0.0262(2) Uani 1 1 d . . . . .
O008 O 0.28779(11) 0.13894(17) 0.28519(4) 0.0413(3) Uani 1 1 d . . . . .
N1 N 0.49436(10) 0.65897(17) 0.57723(4) 0.0247(3) Uani 1 1 d . . . . .
N2 N 0.63479(10) 0.76245(17) 0.53570(4) 0.0261(3) Uani 1 1 d . . . . .
N3 N 0.59940(9) 0.81780(16) 0.46435(4) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.548692 0.820765 0.442876 0.027 Uiso 1 1 calc R . . . .
N4 N 0.19002(10) 0.36280(17) 0.34446(4) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.26298(11) 0.66670(18) 0.47285(4) 0.0202(3) Uani 1 1 d . . . . .
C1A C 0.41036(15) -0.2690(3) 0.77933(6) 0.0419(4) Uani 1 1 d . . . . .
H1A H 0.433181 -0.389557 0.784705 0.050 Uiso 1 1 calc R . . . .
C2 C 0.23085(11) 0.62405(18) 0.51369(5) 0.0202(3) Uani 1 1 d . . . . .
C2A C 0.34838(15) -0.1811(3) 0.80710(6) 0.0393(4) Uani 1 1 d . . . . .
H2AA H 0.328467 -0.240798 0.831579 0.047 Uiso 1 1 calc R . . . .
C3 C 0.30725(11) 0.62403(18) 0.54768(5) 0.0213(3) Uani 1 1 d . . . . .
H3A H 0.285874 0.594045 0.574672 0.026 Uiso 1 1 calc R . . . .
C3A C 0.31545(14) -0.0057(2) 0.79906(5) 0.0358(4) Uani 1 1 d . . . . .
H3AA H 0.271231 0.054116 0.817747 0.043 Uiso 1 1 calc R . . . .
C4 C 0.41835(11) 0.66865(18) 0.54274(4) 0.0203(3) Uani 1 1 d . . . . .
C4A C 0.34638(13) 0.0832(2) 0.76407(5) 0.0308(3) Uani 1 1 d . . . . .
H4A H 0.324516 0.204571 0.759228 0.037 Uiso 1 1 calc R . . . .
C5 C 0.44926(11) 0.71902(17) 0.50319(4) 0.0191(3) Uani 1 1 d . . . . .
C5A C 0.40937(12) -0.0031(2) 0.73576(5) 0.0285(3) Uani 1 1 d . . . . .
C6 C 0.36933(11) 0.71728(19) 0.46807(4) 0.0211(3) Uani 1 1 d . . . . .
H6 H 0.389522 0.751247 0.441155 0.025 Uiso 1 1 calc R . . . .
C6A C 0.43928(13) -0.1820(2) 0.74375(6) 0.0376(4) Uani 1 1 d . . . . .
H6A H 0.480105 -0.244781 0.724419 0.045 Uiso 1 1 calc R . . . .
C7 C 0.59629(12) 0.7049(2) 0.57130(5) 0.0276(3) Uani 1 1 d . . . . .
H7 H 0.648819 0.696099 0.595104 0.033 Uiso 1 1 calc R . . . .
C7A C 0.44420(12) 0.0853(2) 0.69812(5) 0.0303(3) Uani 1 1 d . . . . .
H7A H 0.472688 0.010187 0.677645 0.036 Uiso 1 1 calc R . . . .
C8 C 0.56321(11) 0.76678(18) 0.50149(5) 0.0200(3) Uani 1 1 d . . . . .
C8A C 0.43974(13) 0.2603(2) 0.68991(5) 0.0311(4) Uani 1 1 d . . . . .
H8A H 0.415518 0.339550 0.710481 0.037 Uiso 1 1 calc R . . . .
C9 C 0.70690(11) 0.86684(18) 0.45524(5) 0.0223(3) Uani 1 1 d . . . . .
C9A C 0.47110(12) 0.3361(2) 0.64994(5) 0.0282(3) Uani 1 1 d . . . . .
C10 C 0.80284(12) 0.8332(2) 0.48134(5) 0.0270(3) Uani 1 1 d . . . . .
H10 H 0.798758 0.777864 0.507942 0.032 Uiso 1 1 calc R . . . .
C11 C 0.90473(13) 0.8812(2) 0.46810(6) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.970540 0.856223 0.485476 0.037 Uiso 1 1 calc R . . . .
C12 C 0.91046(12) 0.9643(2) 0.43018(6) 0.0308(4) Uani 1 1 d . . . . .
C13 C 0.81607(13) 1.00000(19) 0.40404(5) 0.0281(3) Uani 1 1 d . . . . .
C14 C 0.71409(12) 0.95033(19) 0.41649(5) 0.0251(3) Uani 1 1 d . . . . .
H14 H 0.648909 0.973225 0.398575 0.030 Uiso 1 1 calc R . . . .
C15 C 0.20734(12) 0.6978(2) 0.39979(5) 0.0245(3) Uani 1 1 d . . . . .
H15A H 0.274258 0.633341 0.392584 0.029 Uiso 1 1 calc R . . . .
H15B H 0.221157 0.828622 0.398256 0.029 Uiso 1 1 calc R . . . .
C16 C 0.08338(12) 0.5520(2) 0.55473(5) 0.0278(3) Uani 1 1 d . . . . .
H16A H 0.004877 0.520401 0.551099 0.042 Uiso 1 1 calc GR . . . .
H16B H 0.093379 0.660131 0.572162 0.042 Uiso 1 1 calc GR . . . .
H16C H 0.125302 0.452494 0.568480 0.042 Uiso 1 1 calc GR . . . .
C17 C 0.10918(12) 0.6460(2) 0.36973(5) 0.0271(3) Uani 1 1 d . . . . .
H17A H 0.116621 0.703271 0.342172 0.032 Uiso 1 1 calc R . . . .
H17B H 0.041156 0.693278 0.380542 0.032 Uiso 1 1 calc R . . . .
C18 C 0.09734(12) 0.4441(2) 0.36352(5) 0.0269(3) Uani 1 1 d . . . . .
H18A H 0.090482 0.386771 0.391114 0.032 Uiso 1 1 calc R . . . .
H18B H 0.028497 0.419466 0.345437 0.032 Uiso 1 1 calc R . . . .
C19 C 0.19482(16) 0.4166(3) 0.30070(5) 0.0400(4) Uani 1 1 d . . . . .
H19A H 0.200582 0.549009 0.298901 0.048 Uiso 1 1 calc R . . . .
H19B H 0.126403 0.378721 0.283847 0.048 Uiso 1 1 calc R . . . .
C20 C 0.29345(18) 0.3308(3) 0.28340(6) 0.0447(5) Uani 1 1 d . . . . .
H20A H 0.296816 0.369027 0.253876 0.054 Uiso 1 1 calc R . . . .
H20B H 0.361735 0.372267 0.299789 0.054 Uiso 1 1 calc R . . . .
C21 C 0.28179(16) 0.0847(2) 0.32729(6) 0.0385(4) Uani 1 1 d . . . . .
H21A H 0.350354 0.121013 0.344256 0.046 Uiso 1 1 calc R . . . .
H21B H 0.276361 -0.047905 0.328429 0.046 Uiso 1 1 calc R . . . .
C22 C 0.18337(14) 0.1668(2) 0.34607(6) 0.0354(4) Uani 1 1 d . . . . .
H22A H 0.114252 0.125748 0.330171 0.043 Uiso 1 1 calc R . . . .
H22B H 0.182270 0.127058 0.375589 0.043 Uiso 1 1 calc R . . . .


_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
Cl1 C13 1.7259(17) . ?
F1 C12 1.3555(16) . ?
O1A C9A 1.2277(19) . ?
O2A C9A 1.312(2) . ?
O003 C2 1.3558(16) . ?
O003 C16 1.4293(17) . ?
O004 C1 1.3561(16) . ?
O004 C15 1.4364(17) . ?
O008 C20 1.431(2) . ?
O008 C21 1.413(2) . ?
N1 C4 1.3741(18) . ?
N1 C7 1.3164(19) . ?
N2 C7 1.340(2) . ?
N2 C8 1.3343(18) . ?
N3 C8 1.3573(18) . ?
N3 C9 1.4134(17) . ?
N4 C18 1.4606(18) . ?
N4 C19 1.461(2) . ?
N4 C22 1.462(2) . ?
C1 C2 1.432(2) . ?
C1 C6 1.3691(18) . ?
C1A C2A 1.381(3) . ?
C1A C6A 1.382(3) . ?
C2 C3 1.364(2) . ?
C2A C3A 1.383(3) . ?
C3 C4 1.4144(19) . ?
C3A C4A 1.381(2) . ?
C4 C5 1.4024(19) . ?
C4A C5A 1.395(2) . ?
C5 C6 1.4163(19) . ?
C5 C8 1.4369(18) . ?
C5A C6A 1.398(2) . ?
C5A C7A 1.467(2) . ?
C7A C8A 1.328(2) . ?
C8A C9A 1.478(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.368(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.387(2) . ?
C15 C17 1.512(2) . ?
C17 C18 1.521(2) . ?
C19 C20 1.508(2) . ?
C21 C22 1.516(2) . ?

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
C2 O003 C16 117.26(11) . . ?
C1 O004 C15 117.05(11) . . ?
C21 O008 C20 109.26(13) . . ?
C7 N1 C4 116.39(13) . . ?
C8 N2 C7 116.81(13) . . ?
C8 N3 C9 129.23(13) . . ?
C18 N4 C19 112.67(12) . . ?
C18 N4 C22 110.57(12) . . ?
C19 N4 C22 108.31(13) . . ?
O004 C1 C2 114.52(12) . . ?
O004 C1 C6 125.33(13) . . ?
C6 C1 C2 120.14(13) . . ?
C2A C1A C6A 120.13(17) . . ?
O003 C2 C1 114.44(12) . . ?
O003 C2 C3 125.34(13) . . ?
C3 C2 C1 120.21(12) . . ?
C1A C2A C3A 119.60(16) . . ?
C2 C3 C4 119.98(13) . . ?
C4A C3A C2A 120.47(17) . . ?
N1 C4 C3 118.54(13) . . ?
N1 C4 C5 121.39(12) . . ?
C5 C4 C3 120.06(13) . . ?
C3A C4A C5A 120.73(16) . . ?
C4 C5 C6 119.39(12) . . ?
C4 C5 C8 116.06(13) . . ?
C6 C5 C8 124.55(13) . . ?
C4A C5A C6A 118.02(15) . . ?
C4A C5A C7A 122.82(15) . . ?
C6A C5A C7A 119.16(15) . . ?
C1 C6 C5 120.08(13) . . ?
C1A C6A C5A 121.00(17) . . ?
N1 C7 N2 127.75(14) . . ?
C8A C7A C5A 126.30(16) . . ?
N2 C8 N3 118.94(13) . . ?
N2 C8 C5 121.50(13) . . ?
N3 C8 C5 119.56(13) . . ?
C7A C8A C9A 122.41(15) . . ?
C10 C9 N3 124.76(14) . . ?
C10 C9 C14 119.62(13) . . ?
C14 C9 N3 115.59(13) . . ?
O1A C9A O2A 124.11(15) . . ?
O1A C9A C8A 123.77(15) . . ?
O2A C9A C8A 112.11(14) . . ?
C11 C10 C9 119.46(15) . . ?
C12 C11 C10 120.27(15) . . ?
F1 C12 C11 119.73(15) . . ?
F1 C12 C13 119.25(15) . . ?
C11 C12 C13 121.02(14) . . ?
C12 C13 Cl1 120.39(12) . . ?
C12 C13 C14 119.39(15) . . ?
C14 C13 Cl1 120.20(13) . . ?
C13 C14 C9 120.23(14) . . ?
O004 C15 C17 107.10(12) . . ?
C15 C17 C18 113.24(12) . . ?
N4 C18 C17 113.34(12) . . ?
N4 C19 C20 109.73(14) . . ?
O008 C20 C19 111.42(16) . . ?
O008 C21 C22 111.92(14) . . ?
N4 C22 C21 109.87(13) . . ?

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
O2A H2A N1 0.84 1.76 2.5893(17) 170.4 . yes

_olex2_submission_special_instructions 'No special instructions were received'
