# 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_ERLO_FURO_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1832313'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE 
India
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 N3 O4, C12 H10 Cl N2 O5 S'
_chemical_formula_sum            'C34 H34 Cl N5 O9 S'
_chemical_formula_weight         724.17

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'
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'
S S 0.1246 0.1234 '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'

_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                   15.3649(5)
_cell_length_b                   10.2088(4)
_cell_length_c                   23.5463(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.752(2)
_cell_angle_gamma                90
_cell_volume                     3536.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9835
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      32.74

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8986
_exptl_absorpt_correction_T_max  0.9307
_exptl_absorpt_process_details   SADABS,(BRUKER,2006)
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            79572
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         33.880
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13049
_reflns_number_gt                10068
_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       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;    
Bruker SHELXTL (Bruker, 2006), ORTEP3 (Farrugia, 2012), 
Mercury CSD 4.2 (Macrae et al., 2008)
;
_computing_publication_material  
;  
Bruker SHELXTL (Bruker, 2006), PLATON (Spek, 2009)
;
_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)+(0.0575P)²+0.9012P] 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_number_reflns         13049
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_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
S1 S 0.89893(2) 0.15783(3) 0.22403(2) 0.02160(6) Uani 1 1 d . . . . .
O1 O -0.06130(5) 0.66670(8) 0.63150(4) 0.02262(16) Uani 1 1 d . . . . .
O2 O -0.14811(8) 0.81895(14) 0.69574(5) 0.0500(3) Uani 1 1 d . . . . .
O3 O 0.03717(5) 0.47712(8) 0.68085(4) 0.02294(16) Uani 1 1 d . . . . .
O4 O 0.05447(7) 0.43053(10) 0.79861(4) 0.03111(19) Uani 1 1 d . . . . .
N1 N 0.07457(6) 0.67125(9) 0.47145(4) 0.01964(17) Uani 1 1 d . . . . .
H1N H 0.0307(16) 0.744(3) 0.4480(11) 0.088(8) Uiso 1 1 d . . . . .
N2 N 0.19193(6) 0.52270(9) 0.47027(4) 0.02044(18) Uani 1 1 d . . . . .
N3 N 0.26133(6) 0.39544(10) 0.55196(4) 0.02059(18) Uani 1 1 d . . . . .
H3N H 0.2623(10) 0.3695(15) 0.5864(7) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.13111(8) 0.61423(11) 0.44618(5) 0.0214(2) Uani 1 1 d . . . . .
H1 H 0.1279 0.6413 0.4070 0.026 Uiso 1 1 calc R U . . .
C2 C 0.19567(7) 0.48180(10) 0.52509(5) 0.01782(19) Uani 1 1 d . . . . .
C3 C 0.12285(7) 0.47458(10) 0.60868(5) 0.01863(19) Uani 1 1 d . . . . .
H3 H 0.1623 0.4067 0.6285 0.022 Uiso 1 1 calc R U . . .
C4 C 0.05716(7) 0.52269(10) 0.63203(5) 0.01818(19) Uani 1 1 d . . . . .
C5 C -0.00002(7) 0.62851(10) 0.60352(5) 0.01842(19) Uani 1 1 d . . . . .
C6 C 0.00759(7) 0.68048(11) 0.55153(5) 0.01897(19) Uani 1 1 d . . . . .
H6 H -0.0300 0.7513 0.5329 0.023 Uiso 1 1 calc R U . . .
C7 C 0.07210(7) 0.62687(10) 0.52624(5) 0.01742(19) Uani 1 1 d . . . . .
C8 C 0.13152(7) 0.52666(10) 0.55484(4) 0.01707(18) Uani 1 1 d . . . . .
C9 C 0.32234(7) 0.33058(11) 0.52625(5) 0.01917(19) Uani 1 1 d . . . . .
C10 C 0.36221(8) 0.39177(12) 0.48734(5) 0.0231(2) Uani 1 1 d . . . . .
H10 H 0.3505 0.4817 0.4777 0.028 Uiso 1 1 calc R U . . .
C11 C 0.41967(8) 0.32044(13) 0.46245(5) 0.0252(2) Uani 1 1 d . . . . .
C12 C 0.43789(9) 0.18891(13) 0.47744(6) 0.0294(3) Uani 1 1 d . . . . .
H12 H 0.4759 0.1397 0.4599 0.035 Uiso 1 1 calc R U . . .
C13 C 0.40026(9) 0.13062(13) 0.51792(6) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.4141 0.0418 0.5290 0.037 Uiso 1 1 calc R U . . .
C14 C 0.34251(8) 0.20034(12) 0.54254(6) 0.0252(2) Uani 1 1 d . . . . .
H14 H 0.3169 0.1596 0.5703 0.030 Uiso 1 1 calc R U . . .
C15 C 0.45859(10) 0.38254(15) 0.42073(7) 0.0361(3) Uani 1 1 d . . . . .
C16 C 0.48975(14) 0.43277(19) 0.38562(8) 0.0529(4) Uani 1 1 d . . . . .
H16 H 0.5147 0.4730 0.3575 0.063 Uiso 1 1 calc R U . . .
C17 C -0.12568(8) 0.76641(12) 0.60361(5) 0.0239(2) Uani 1 1 d . . . . .
H17A H -0.1559 0.7433 0.5617 0.029 Uiso 1 1 calc R U . . .
H17B H -0.0947 0.8518 0.6047 0.029 Uiso 1 1 calc R U . . .
C18 C -0.19361(9) 0.77326(15) 0.63791(6) 0.0335(3) Uani 1 1 d . . . . .
H18A H -0.2435 0.8339 0.6183 0.040 Uiso 1 1 calc R U . . .
H18B H -0.2199 0.6855 0.6400 0.040 Uiso 1 1 calc R U . . .
C19 C -0.20454(17) 0.8231(3) 0.73345(10) 0.0916(10) Uani 1 1 d . . . . .
H19A H -0.2559 0.8818 0.7166 0.137 Uiso 1 1 calc R U . . .
H19B H -0.1697 0.8555 0.7726 0.137 Uiso 1 1 calc R U . . .
H19C H -0.2272 0.7349 0.7374 0.137 Uiso 1 1 calc R U . . .
C20 C 0.08429(8) 0.36270(11) 0.70968(5) 0.0224(2) Uani 1 1 d . . . . .
H20A H 0.1496 0.3819 0.7278 0.027 Uiso 1 1 calc R U . . .
H20B H 0.0786 0.2901 0.6810 0.027 Uiso 1 1 calc R U . . .
C21 C 0.03962(9) 0.32729(12) 0.75650(5) 0.0267(2) Uani 1 1 d . . . . .
H21A H -0.0264 0.3142 0.7382 0.032 Uiso 1 1 calc R U . . .
H21B H 0.0657 0.2447 0.7763 0.032 Uiso 1 1 calc R U . . .
C22 C -0.00979(13) 0.43263(19) 0.83086(8) 0.0505(4) Uani 1 1 d . . . . .
H22A H -0.0706 0.4473 0.8036 0.076 Uiso 1 1 calc R U . . .
H22B H 0.0051 0.5034 0.8602 0.076 Uiso 1 1 calc R U . . .
H22C H -0.0086 0.3486 0.8512 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl 0.75588(2) 0.36396(3) 0.25720(2) 0.02477(7) Uani 1 1 d . . . . .
O5 O 0.81944(6) 0.18449(10) 0.17538(4) 0.0304(2) Uani 1 1 d . . . . .
O6 O 0.95018(7) 0.04148(9) 0.22226(4) 0.0331(2) Uani 1 1 d . . . . .
O7 O 0.98334(6) -0.14310(9) 0.40873(4) 0.02750(18) Uani 1 1 d . . . . .
O8 O 0.88908(7) -0.11085(11) 0.46405(5) 0.0392(2) Uani 1 1 d . . . . .
O9 O 0.65057(8) 0.21403(14) 0.53757(5) 0.0524(3) Uani 1 1 d . . . . .
N4 N 0.96697(8) 0.27970(11) 0.22852(5) 0.0253(2) Uani 1 1 d . . . . .
H4NA H 0.9434(13) 0.3525(19) 0.2273(8) 0.041(5) Uiso 1 1 d . . . . .
H4NB H 1.0164(12) 0.2703(18) 0.2577(8) 0.042(5) Uiso 1 1 d . . . . .
N5 N 0.78419(7) 0.09823(11) 0.44315(5) 0.0252(2) Uani 1 1 d . . . . .
H5N H 0.8065(11) 0.0311(17) 0.4632(7) 0.036(4) Uiso 1 1 d . . . . .
C23 C 0.86540(7) 0.14791(10) 0.28934(4) 0.01814(19) Uani 1 1 d . . . . .
C24 C 0.80222(7) 0.23258(10) 0.30273(5) 0.01829(19) Uani 1 1 d . . . . .
C25 C 0.77404(7) 0.21544(11) 0.35269(5) 0.0195(2) Uani 1 1 d . . . . .
H25 H 0.7298 0.2729 0.3600 0.023 Uiso 1 1 calc R U . . .
C26 C 0.81013(7) 0.11331(11) 0.39324(5) 0.01888(19) Uani 1 1 d . . . . .
C27 C 0.87639(7) 0.02875(10) 0.38100(5) 0.01829(19) Uani 1 1 d . . . . .
C28 C 0.90171(7) 0.04815(10) 0.32975(5) 0.01857(19) Uani 1 1 d . . . . .
H28 H 0.9456 -0.0088 0.3218 0.022 Uiso 1 1 calc R U . . .
C29 C 0.91838(8) -0.08241(11) 0.42161(5) 0.0228(2) Uani 1 1 d . . . . .
C30 C 0.71641(8) 0.17798(13) 0.45798(6) 0.0269(2) Uani 1 1 d . . . . .
H30A H 0.6552 0.1532 0.4326 0.032 Uiso 1 1 calc R U . . .
H30B H 0.7268 0.2713 0.4505 0.032 Uiso 1 1 calc R U . . .
C31 C 0.72113(9) 0.15956(13) 0.52151(6) 0.0310(3) Uani 1 1 d . . . . .
C32 C 0.78107(11) 0.10507(15) 0.56876(6) 0.0381(3) Uani 1 1 d . . . . .
H32 H 0.8359 0.0613 0.5695 0.046 Uiso 1 1 calc R U . . .
C33 C 0.74527(15) 0.1265(2) 0.61793(8) 0.0534(5) Uani 1 1 d . . . . .
H33 H 0.7717 0.0991 0.6577 0.064 Uiso 1 1 calc R U . . .
C34 C 0.66816(15) 0.1920(3) 0.59704(9) 0.0664(6) Uani 1 1 d . . . . .
H34 H 0.6303 0.2198 0.6203 0.080 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
S1 O6 1.4323(10) . ?
S1 O5 1.4392(9) . ?
S1 N4 1.6088(11) . ?
S1 C23 1.7600(11) . ?
O1 C5 1.3528(13) . ?
O1 C17 1.4393(13) . ?
O2 C19 1.409(2) . ?
O2 C18 1.4184(18) . ?
O3 C4 1.3550(13) . ?
O3 C20 1.4374(13) . ?
O4 C22 1.4086(17) . ?
O4 C21 1.4198(16) . ?
N1 C1 1.3210(15) . ?
N1 C7 1.3782(14) . ?
N1 H1N 1.04(3) . ?
N2 C1 1.3277(14) . ?
N2 C2 1.3421(13) . ?
N3 C2 1.3518(13) . ?
N3 C9 1.4181(14) . ?
N3 H3N 0.848(16) . ?
C1 H1 0.9500 . ?
C2 C8 1.4386(14) . ?
C3 C4 1.3718(15) . ?
C3 C8 1.4160(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.4316(15) . ?
C5 C6 1.3698(15) . ?
C6 C7 1.4061(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.4068(14) . ?
C9 C10 1.3887(15) . ?
C9 C14 1.3936(16) . ?
C10 C11 1.3971(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3960(18) . ?
C11 C15 1.4363(18) . ?
C12 C13 1.3837(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3880(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.185(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.4941(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.5012(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
Cl1 C24 1.7363(11) . ?
O7 C29 1.2832(14) . ?
O8 C29 1.2427(14) . ?
O9 C31 1.3654(16) . ?
O9 C34 1.366(2) . ?
N4 H4NA 0.824(19) . ?
N4 H4NB 0.870(19) . ?
N5 C26 1.3541(14) . ?
N5 C30 1.4419(15) . ?
N5 H5N 0.846(17) . ?
C23 C28 1.3956(15) . ?
C23 C24 1.4019(15) . ?
C24 C25 1.3767(15) . ?
C25 C26 1.4146(15) . ?
C25 H25 0.9500 . ?
C26 C27 1.4262(15) . ?
C27 C28 1.3849(15) . ?
C27 C29 1.5042(15) . ?
C28 H28 0.9500 . ?
C30 C31 1.4886(18) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.343(2) . ?
C32 C33 1.435(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.325(3) . ?
C33 H33 0.9500 . ?
C34 H34 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
O6 S1 O5 118.77(6) . . ?
O6 S1 N4 106.92(6) . . ?
O5 S1 N4 107.01(6) . . ?
O6 S1 C23 106.23(5) . . ?
O5 S1 C23 108.14(5) . . ?
N4 S1 C23 109.59(5) . . ?
C5 O1 C17 117.71(9) . . ?
C19 O2 C18 113.10(16) . . ?
C4 O3 C20 118.24(8) . . ?
C22 O4 C21 113.03(12) . . ?
C1 N1 C7 118.41(9) . . ?
C1 N1 H1N 118.9(13) . . ?
C7 N1 H1N 122.6(13) . . ?
C1 N2 C2 117.35(10) . . ?
C2 N3 C9 126.92(9) . . ?
C2 N3 H3N 117.1(11) . . ?
C9 N3 H3N 115.5(11) . . ?
N1 C1 N2 126.23(10) . . ?
N1 C1 H1 116.9 . . ?
N2 C1 H1 116.9 . . ?
N2 C2 N3 118.18(10) . . ?
N2 C2 C8 121.60(9) . . ?
N3 C2 C8 120.22(9) . . ?
C4 C3 C8 119.62(10) . . ?
C4 C3 H3 120.2 . . ?
C8 C3 H3 120.2 . . ?
O3 C4 C3 126.15(10) . . ?
O3 C4 C5 113.47(9) . . ?
C3 C4 C5 120.35(10) . . ?
O1 C5 C6 125.04(10) . . ?
O1 C5 C4 114.10(9) . . ?
C6 C5 C4 120.82(10) . . ?
C5 C6 C7 118.68(10) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
N1 C7 C6 118.78(9) . . ?
N1 C7 C8 119.87(10) . . ?
C6 C7 C8 121.31(10) . . ?
C7 C8 C3 119.09(9) . . ?
C7 C8 C2 116.07(9) . . ?
C3 C8 C2 124.81(9) . . ?
C10 C9 C14 120.35(10) . . ?
C10 C9 N3 122.90(10) . . ?
C14 C9 N3 116.74(10) . . ?
C9 C10 C11 119.64(11) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 120.01(11) . . ?
C12 C11 C15 120.32(12) . . ?
C10 C11 C15 119.66(12) . . ?
C13 C12 C11 119.65(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.76(12) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 119.51(11) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
C16 C15 C11 178.98(19) . . ?
C15 C16 H16 180.0 . . ?
O1 C17 C18 106.36(10) . . ?
O1 C17 H17A 110.5 . . ?
C18 C17 H17A 110.5 . . ?
O1 C17 H17B 110.5 . . ?
C18 C17 H17B 110.5 . . ?
H17A C17 H17B 108.6 . . ?
O2 C18 C17 107.85(11) . . ?
O2 C18 H18A 110.1 . . ?
C17 C18 H18A 110.1 . . ?
O2 C18 H18B 110.1 . . ?
C17 C18 H18B 110.1 . . ?
H18A C18 H18B 108.4 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C21 105.54(9) . . ?
O3 C20 H20A 110.6 . . ?
C21 C20 H20A 110.6 . . ?
O3 C20 H20B 110.6 . . ?
C21 C20 H20B 110.6 . . ?
H20A C20 H20B 108.8 . . ?
O4 C21 C20 108.58(10) . . ?
O4 C21 H21A 110.0 . . ?
C20 C21 H21A 110.0 . . ?
O4 C21 H21B 110.0 . . ?
C20 C21 H21B 110.0 . . ?
H21A C21 H21B 108.4 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C31 O9 C34 106.17(14) . . ?
S1 N4 H4NA 115.1(13) . . ?
S1 N4 H4NB 111.7(12) . . ?
H4NA N4 H4NB 113.7(17) . . ?
C26 N5 C30 124.03(10) . . ?
C26 N5 H5N 113.8(11) . . ?
C30 N5 H5N 121.7(11) . . ?
C28 C23 C24 117.60(10) . . ?
C28 C23 S1 118.53(8) . . ?
C24 C23 S1 123.85(8) . . ?
C25 C24 C23 121.50(9) . . ?
C25 C24 Cl1 116.85(8) . . ?
C23 C24 Cl1 121.65(8) . . ?
C24 C25 C26 120.79(10) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
N5 C26 C25 120.90(10) . . ?
N5 C26 C27 120.82(10) . . ?
C25 C26 C27 118.26(10) . . ?
C28 C27 C26 119.06(9) . . ?
C28 C27 C29 119.02(9) . . ?
C26 C27 C29 121.91(10) . . ?
C27 C28 C23 122.75(10) . . ?
C27 C28 H28 118.6 . . ?
C23 C28 H28 118.6 . . ?
O8 C29 O7 124.33(11) . . ?
O8 C29 C27 119.93(10) . . ?
O7 C29 C27 115.74(10) . . ?
N5 C30 C31 110.04(11) . . ?
N5 C30 H30A 109.7 . . ?
C31 C30 H30A 109.7 . . ?
N5 C30 H30B 109.7 . . ?
C31 C30 H30B 109.7 . . ?
H30A C30 H30B 108.2 . . ?
C32 C31 O9 110.41(13) . . ?
C32 C31 C30 135.05(13) . . ?
O9 C31 C30 114.48(12) . . ?
C31 C32 C33 105.92(15) . . ?
C31 C32 H32 127.0 . . ?
C33 C32 H32 127.0 . . ?
C34 C33 C32 106.68(16) . . ?
C34 C33 H33 126.7 . . ?
C32 C33 H33 126.7 . . ?
C33 C34 O9 110.81(15) . . ?
C33 C34 H34 124.6 . . ?
O9 C34 H34 124.6 . . ?

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
C7 N1 C1 N2 -5.24(17) . . . . ?
C2 N2 C1 N1 1.35(17) . . . . ?
C1 N2 C2 N3 -175.45(10) . . . . ?
C1 N2 C2 C8 5.16(15) . . . . ?
C9 N3 C2 N2 -7.39(17) . . . . ?
C9 N3 C2 C8 172.00(10) . . . . ?
C20 O3 C4 C3 -4.13(16) . . . . ?
C20 O3 C4 C5 174.03(9) . . . . ?
C8 C3 C4 O3 175.53(10) . . . . ?
C8 C3 C4 C5 -2.51(16) . . . . ?
C17 O1 C5 C6 2.29(16) . . . . ?
C17 O1 C5 C4 -175.77(9) . . . . ?
O3 C4 C5 O1 2.16(13) . . . . ?
C3 C4 C5 O1 -179.56(10) . . . . ?
O3 C4 C5 C6 -175.99(10) . . . . ?
C3 C4 C5 C6 2.29(16) . . . . ?
O1 C5 C6 C7 -177.24(10) . . . . ?
C4 C5 C6 C7 0.69(16) . . . . ?
C1 N1 C7 C6 -175.46(10) . . . . ?
C1 N1 C7 C8 2.48(15) . . . . ?
C5 C6 C7 N1 174.48(10) . . . . ?
C5 C6 C7 C8 -3.44(16) . . . . ?
N1 C7 C8 C3 -174.68(10) . . . . ?
C6 C7 C8 C3 3.21(15) . . . . ?
N1 C7 C8 C2 3.33(15) . . . . ?
C6 C7 C8 C2 -178.77(9) . . . . ?
C4 C3 C8 C7 -0.18(16) . . . . ?
C4 C3 C8 C2 -178.01(10) . . . . ?
N2 C2 C8 C7 -7.32(15) . . . . ?
N3 C2 C8 C7 173.31(10) . . . . ?
N2 C2 C8 C3 170.57(10) . . . . ?
N3 C2 C8 C3 -8.80(16) . . . . ?
C2 N3 C9 C10 39.64(17) . . . . ?
C2 N3 C9 C14 -141.33(12) . . . . ?
C14 C9 C10 C11 2.83(17) . . . . ?
N3 C9 C10 C11 -178.18(11) . . . . ?
C9 C10 C11 C12 -1.00(18) . . . . ?
C9 C10 C11 C15 178.00(12) . . . . ?
C10 C11 C12 C13 -1.33(19) . . . . ?
C15 C11 C12 C13 179.68(13) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C12 C13 C14 C9 0.0(2) . . . . ?
C10 C9 C14 C13 -2.32(18) . . . . ?
N3 C9 C14 C13 178.62(11) . . . . ?
C5 O1 C17 C18 170.74(10) . . . . ?
C19 O2 C18 C17 -176.91(17) . . . . ?
O1 C17 C18 O2 65.72(14) . . . . ?
C4 O3 C20 C21 -173.04(10) . . . . ?
C22 O4 C21 C20 157.77(12) . . . . ?
O3 C20 C21 O4 -63.94(12) . . . . ?
O6 S1 C23 C28 8.69(10) . . . . ?
O5 S1 C23 C28 137.20(9) . . . . ?
N4 S1 C23 C28 -106.48(9) . . . . ?
O6 S1 C23 C24 -169.60(9) . . . . ?
O5 S1 C23 C24 -41.08(11) . . . . ?
N4 S1 C23 C24 75.24(10) . . . . ?
C28 C23 C24 C25 -2.46(15) . . . . ?
S1 C23 C24 C25 175.83(8) . . . . ?
C28 C23 C24 Cl1 177.48(8) . . . . ?
S1 C23 C24 Cl1 -4.22(13) . . . . ?
C23 C24 C25 C26 1.79(16) . . . . ?
Cl1 C24 C25 C26 -178.15(8) . . . . ?
C30 N5 C26 C25 3.01(17) . . . . ?
C30 N5 C26 C27 -178.69(11) . . . . ?
C24 C25 C26 N5 178.36(10) . . . . ?
C24 C25 C26 C27 0.02(15) . . . . ?
N5 C26 C27 C28 -179.41(10) . . . . ?
C25 C26 C27 C28 -1.07(15) . . . . ?
N5 C26 C27 C29 1.70(16) . . . . ?
C25 C26 C27 C29 -179.96(10) . . . . ?
C26 C27 C28 C23 0.35(16) . . . . ?
C29 C27 C28 C23 179.28(10) . . . . ?
C24 C23 C28 C27 1.39(16) . . . . ?
S1 C23 C28 C27 -177.00(8) . . . . ?
C28 C27 C29 O8 -171.67(12) . . . . ?
C26 C27 C29 O8 7.22(17) . . . . ?
C28 C27 C29 O7 7.65(15) . . . . ?
C26 C27 C29 O7 -173.46(10) . . . . ?
C26 N5 C30 C31 -165.43(11) . . . . ?
C34 O9 C31 C32 0.04(19) . . . . ?
C34 O9 C31 C30 -177.69(15) . . . . ?
N5 C30 C31 C32 13.1(2) . . . . ?
N5 C30 C31 O9 -169.88(11) . . . . ?
O9 C31 C32 C33 0.23(17) . . . . ?
C30 C31 C32 C33 177.32(15) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 O9 0.5(2) . . . . ?
C31 O9 C34 C33 -0.3(2) . . . . ?

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
N4 H4NA O3 0.824(19) 2.724(18) 3.2862(14) 127.0(16) 3_666
C16 H16 O6 0.95 2.21 3.1446(18) 167.4 2_655
N5 H5N O8 0.846(17) 1.923(17) 2.6340(14) 140.8(16) .
N4 H4NB O2 0.870(19) 2.202(19) 3.0131(16) 155.0(16) 3_666
N4 H4NB O1 0.870(19) 2.580(18) 3.2419(13) 133.6(15) 3_666
N4 H4NA O4 0.824(19) 2.300(19) 3.0243(15) 147.0(17) 3_666
C20 H20B O7 0.99 2.54 3.4941(15) 161.4 3_656
C20 H20A Cl1 0.99 2.97 3.4434(11) 110.8 4_566
C20 H20A Cl1 0.99 2.94 3.6499(12) 129.0 3_666
C6 H6 O8 0.95 2.23 3.1519(14) 162.0 1_465
C3 H3 O5 0.95 2.53 3.3901(14) 151.4 4_566
N3 H3N O5 0.848(16) 2.099(16) 2.9005(13) 157.3(15) 4_566
N1 H1N O8 1.04(3) 2.75(2) 3.5799(13) 136.6(17) 1_465
N1 H1N O7 1.04(3) 1.53(3) 2.5582(12) 168(2) 1_465

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-butanol'
####################################################################### 
# 
# 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_GIF_MEF_H2O
_database_code_depnum_ccdc_archive 'CCDC 1984252'
loop_
_audit_author_name
_audit_author_address
'Dr. Rajesh G. Gonnade'
;CSIR NATIONAL CHEMICAL LABORATORY PUNE INDIA
India
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-08-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_GIF_MEF_H2O         
;
PROBLEM: D-H Without Acceptor O44 --H6A . Please Check
RESPONSE: H6A is the water hydrogen atom which has been fixed stereochemically.
H6B make hydrogen bond but not H6A.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'Gefitinib-mefenamic acid cocrystal'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Cl F N4 O3, C15 H15 N1 O2, H2 O'
_chemical_formula_sum            'C37 H41 Cl F N5 O6'
_chemical_formula_weight         706.20

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'
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'
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'

_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                   10.9083(7)
_cell_length_b                   7.6817(5)
_cell_length_c                   41.588(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.132(4)
_cell_angle_gamma                90
_cell_volume                     3464.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5596
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      21.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS (BRUKER, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'Photon II CPAD Area Detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            40768
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6829
_reflns_number_gt                4764
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0597P)²+13.2995P] 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_number_reflns         6829
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.2177
_refine_ls_wR_factor_gt          0.1998
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.11466(13) 1.1043(2) 0.62819(3) 0.0531(4) Uani 1 1 d . . . . .
F1 F -0.1003(3) 1.0024(4) 0.58429(7) 0.0436(8) Uani 1 1 d . . . . .
N1 N 0.4575(3) 0.8190(5) 0.45141(9) 0.0262(9) Uani 1 1 d . . . . .
C2 C 0.3480(4) 0.8745(6) 0.45869(11) 0.0303(11) Uani 1 1 d . . . . .
H2 H 0.2932 0.9189 0.4413 0.036 Uiso 1 1 calc R U . . .
N3 N 0.3079(4) 0.8741(5) 0.48766(9) 0.0315(9) Uani 1 1 d . . . . .
C4 C 0.3849(4) 0.8131(6) 0.51244(11) 0.0270(10) Uani 1 1 d . . . . .
N4 N 0.3466(4) 0.8153(5) 0.54232(10) 0.0295(9) Uani 1 1 d . . . . .
H4N H 0.400(4) 0.795(6) 0.5580(11) 0.018(12) Uiso 1 1 d . . . . .
C5 C 0.5887(4) 0.6745(6) 0.53245(10) 0.0244(10) Uani 1 1 d . . . . .
H5 H 0.5664 0.6661 0.5539 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7026(4) 0.6168(6) 0.52559(10) 0.0241(10) Uani 1 1 d . . . . .
O6 O 0.7891(3) 0.5448(4) 0.54747(7) 0.0281(7) Uani 1 1 d . . . . .
C7 C 0.7364(4) 0.6294(6) 0.49347(10) 0.0222(9) Uani 1 1 d . . . . .
O7 O 0.8514(3) 0.5714(4) 0.49012(7) 0.0265(7) Uani 1 1 d . . . . .
C8 C 0.6548(4) 0.6947(6) 0.46910(11) 0.0240(10) Uani 1 1 d . . . . .
H8 H 0.6765 0.7001 0.4476 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5381(4) 0.7537(5) 0.47620(10) 0.0220(9) Uani 1 1 d . . . . .
C10 C 0.5048(4) 0.7463(6) 0.50769(10) 0.0235(10) Uani 1 1 d . . . . .
C11 C 0.2291(4) 0.8695(6) 0.55102(11) 0.0285(10) Uani 1 1 d . . . . .
C12 C 0.2294(4) 0.9500(6) 0.58096(11) 0.0299(11) Uani 1 1 d . . . . .
H12 H 0.3048 0.9736 0.5939 0.036 Uiso 1 1 calc R U . . .
C13 C 0.1164(5) 0.9956(6) 0.59173(11) 0.0307(11) Uani 1 1 d . . . . .
C14 C 0.0096(4) 0.9609(6) 0.57301(12) 0.0309(11) Uani 1 1 d . . . . .
C15 C 0.0079(5) 0.8861(7) 0.54327(13) 0.0371(12) Uani 1 1 d . . . . .
H15 H -0.0682 0.8652 0.5305 0.044 Uiso 1 1 calc R U . . .
C16 C 0.1191(5) 0.8408(6) 0.53186(13) 0.0356(12) Uani 1 1 d . . . . .
H16 H 0.1195 0.7903 0.5110 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7630(4) 0.5406(6) 0.58048(10) 0.0278(10) Uani 1 1 d . . . . .
H17A H 0.6874 0.4718 0.5824 0.033 Uiso 1 1 calc R U . . .
H17B H 0.7495 0.6602 0.5882 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8701(5) 0.4594(6) 0.60035(10) 0.0295(11) Uani 1 1 d . . . . .
H18A H 0.9432 0.5355 0.6000 0.035 Uiso 1 1 calc R U . . .
H18B H 0.8893 0.3461 0.5907 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8443(5) 0.4314(6) 0.63498(11) 0.0299(11) Uani 1 1 d . . . . .
H19A H 0.7805 0.3402 0.6355 0.036 Uiso 1 1 calc R U . . .
H19B H 0.9204 0.3887 0.6477 0.036 Uiso 1 1 calc R U . . .
N20 N 0.8023(3) 0.5905(5) 0.65037(8) 0.0222(8) Uani 1 1 d . . . . .
C21 C 0.7622(5) 0.5487(6) 0.68162(10) 0.0290(11) Uani 1 1 d . . . . .
H21A H 0.8319 0.4992 0.6959 0.035 Uiso 1 1 calc R U . . .
H21B H 0.6957 0.4605 0.6789 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7150(5) 0.7124(6) 0.69703(12) 0.0326(11) Uani 1 1 d . . . . .
H22A H 0.6439 0.7601 0.6830 0.039 Uiso 1 1 calc R U . . .
H22B H 0.6869 0.6829 0.7182 0.039 Uiso 1 1 calc R U . . .
O23 O 0.8104(3) 0.8404(5) 0.70140(8) 0.0401(9) Uani 1 1 d . . . . .
C24 C 0.8561(5) 0.8796(7) 0.67129(13) 0.0369(12) Uani 1 1 d . . . . .
H24A H 0.9240 0.9651 0.6750 0.044 Uiso 1 1 calc R U . . .
H24B H 0.7894 0.9338 0.6566 0.044 Uiso 1 1 calc R U . . .
C25 C 0.9024(5) 0.7209(6) 0.65524(11) 0.0307(11) Uani 1 1 d . . . . .
H25A H 0.9300 0.7533 0.6341 0.037 Uiso 1 1 calc R U . . .
H25B H 0.9736 0.6710 0.6689 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8957(5) 0.5951(7) 0.45907(11) 0.0324(11) Uani 1 1 d . . . . .
H26A H 0.8415 0.5332 0.4425 0.049 Uiso 1 1 calc R U . . .
H26B H 0.9796 0.5487 0.4597 0.049 Uiso 1 1 calc R U . . .
H26C H 0.8961 0.7194 0.4538 0.049 Uiso 1 1 calc R U . . .
C27 C 0.5276(4) 0.7228(6) 0.37596(10) 0.0241(10) Uani 1 1 d . . . . .
C28 C 0.5120(4) 0.7272(5) 0.34038(10) 0.0183(9) Uani 1 1 d . . . . .
C29 C 0.4311(4) 0.8494(5) 0.32465(10) 0.0223(9) Uani 1 1 d . . . . .
H29 H 0.3937 0.9331 0.3373 0.027 Uiso 1 1 calc R U . . .
C30 C 0.4035(4) 0.8528(6) 0.29139(10) 0.0254(10) Uani 1 1 d . . . . .
H30 H 0.3492 0.9381 0.2813 0.030 Uiso 1 1 calc R U . . .
C31 C 0.4573(4) 0.7284(6) 0.27299(10) 0.0240(10) Uani 1 1 d . . . . .
H31 H 0.4381 0.7274 0.2502 0.029 Uiso 1 1 calc R U . . .
C32 C 0.5379(4) 0.6068(6) 0.28750(9) 0.0212(9) Uani 1 1 d . . . . .
H32 H 0.5737 0.5236 0.2744 0.025 Uiso 1 1 calc R U . . .
C33 C 0.5684(4) 0.6029(5) 0.32119(10) 0.0187(9) Uani 1 1 d . . . . .
N33 N 0.6510(4) 0.4822(5) 0.33513(9) 0.0238(8) Uani 1 1 d . . . . .
H33N H 0.652(4) 0.465(6) 0.3563(12) 0.028(13) Uiso 1 1 d . . . . .
C34 C 0.7042(4) 0.3503(5) 0.31691(9) 0.0192(9) Uani 1 1 d . . . . .
C35 C 0.6679(4) 0.1777(6) 0.32082(10) 0.0244(10) Uani 1 1 d . . . . .
H35 H 0.6101 0.1502 0.3356 0.029 Uiso 1 1 calc R U . . .
C36 C 0.7166(4) 0.0468(6) 0.30304(11) 0.0273(10) Uani 1 1 d . . . . .
H36 H 0.6936 -0.0709 0.3060 0.033 Uiso 1 1 calc R U . . .
C37 C 0.7984(4) 0.0873(6) 0.28107(11) 0.0268(10) Uani 1 1 d . . . . .
H37 H 0.8297 -0.0028 0.2686 0.032 Uiso 1 1 calc R U . . .
C38 C 0.8362(4) 0.2605(6) 0.27686(10) 0.0224(9) Uani 1 1 d . . . . .
C39 C 0.7904(4) 0.3924(5) 0.29545(10) 0.0194(9) Uani 1 1 d . . . . .
C40 C 0.9245(4) 0.3010(6) 0.25251(11) 0.0308(11) Uani 1 1 d . . . . .
H40A H 0.8946 0.4020 0.2396 0.046 Uiso 1 1 calc R U . . .
H40B H 0.9307 0.2004 0.2383 0.046 Uiso 1 1 calc R U . . .
H40C H 1.0060 0.3271 0.2638 0.046 Uiso 1 1 calc R U . . .
C41 C 0.8349(4) 0.5780(6) 0.29238(11) 0.0275(10) Uani 1 1 d . . . . .
H41A H 0.7997 0.6267 0.2716 0.041 Uiso 1 1 calc R U . . .
H41B H 0.9251 0.5791 0.2934 0.041 Uiso 1 1 calc R U . . .
H41C H 0.8089 0.6484 0.3101 0.041 Uiso 1 1 calc R U . . .
O42 O 0.4801(3) 0.8537(4) 0.39058(7) 0.0334(8) Uani 1 1 d . . . . .
O43 O 0.5808(4) 0.6013(5) 0.39148(8) 0.0437(10) Uani 1 1 d . . . . .
H42O H 0.473(5) 0.831(8) 0.4210(13) 0.053(16) Uiso 1 1 d . . . . .
O44 O 0.4990(5) 0.2326(8) 0.39608(13) 0.0775(16) Uani 1 1 d G . . . .
H6A H 0.4271 0.2147 0.3866 0.116 Uiso 1 1 d G U . . .
H6B H 0.5200 0.3374 0.3930 0.116 Uiso 1 1 d G 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
Cl1 C13 1.733(5) . ?
F1 C14 1.371(5) . ?
N1 C2 1.333(6) . ?
N1 C9 1.376(5) . ?
N1 H42O 1.30(5) . ?
C2 N3 1.325(6) . ?
C2 H2 0.9500 . ?
N3 C4 1.342(6) . ?
C4 N4 1.353(6) . ?
C4 C10 1.438(6) . ?
N4 C11 1.431(6) . ?
N4 H4N 0.84(5) . ?
C5 C6 1.378(6) . ?
C5 C10 1.415(6) . ?
C5 H5 0.9500 . ?
C6 O6 1.357(5) . ?
C6 C7 1.426(6) . ?
O6 C17 1.432(5) . ?
C7 O7 1.353(5) . ?
C7 C8 1.370(6) . ?
O7 C26 1.438(5) . ?
C8 C9 1.412(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(6) . ?
C11 C16 1.385(7) . ?
C11 C12 1.390(6) . ?
C12 C13 1.400(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.357(7) . ?
C14 C15 1.362(7) . ?
C15 C16 1.393(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.493(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.512(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N20 1.475(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C21 1.451(5) . ?
N20 C25 1.479(6) . ?
C21 C22 1.525(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O23 1.429(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O23 C24 1.429(6) . ?
C24 C25 1.503(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 O43 1.242(5) . ?
C27 O42 1.310(5) . ?
C27 C28 1.472(6) . ?
C28 C29 1.402(6) . ?
C28 C33 1.425(5) . ?
C29 C30 1.384(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.377(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.405(6) . ?
C32 H32 0.9500 . ?
C33 N33 1.377(5) . ?
N33 C34 1.425(5) . ?
N33 H33N 0.89(5) . ?
C34 C35 1.399(6) . ?
C34 C39 1.402(6) . ?
C35 C36 1.387(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.379(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.409(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.399(6) . ?
C38 C40 1.503(6) . ?
C39 C41 1.516(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
O42 H42O 1.29(5) . ?
O44 H6A 0.8500 . ?
O44 H6B 0.8502 . ?

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 N1 C9 117.6(4) . . ?
C2 N1 H42O 115(2) . . ?
C9 N1 H42O 128(2) . . ?
N3 C2 N1 126.6(4) . . ?
N3 C2 H2 116.7 . . ?
N1 C2 H2 116.7 . . ?
C2 N3 C4 117.3(4) . . ?
N3 C4 N4 118.2(4) . . ?
N3 C4 C10 121.5(4) . . ?
N4 C4 C10 120.3(4) . . ?
C4 N4 C11 127.5(4) . . ?
C4 N4 H4N 117(3) . . ?
C11 N4 H4N 115(3) . . ?
C6 C5 C10 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C10 C5 H5 119.9 . . ?
O6 C6 C5 124.8(4) . . ?
O6 C6 C7 115.1(4) . . ?
C5 C6 C7 120.1(4) . . ?
C6 O6 C17 117.2(3) . . ?
O7 C7 C8 125.5(4) . . ?
O7 C7 C6 114.2(4) . . ?
C8 C7 C6 120.3(4) . . ?
C7 O7 C26 117.1(3) . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
N1 C9 C10 120.5(4) . . ?
N1 C9 C8 118.6(4) . . ?
C10 C9 C8 120.9(4) . . ?
C9 C10 C5 119.1(4) . . ?
C9 C10 C4 116.5(4) . . ?
C5 C10 C4 124.5(4) . . ?
C16 C11 C12 120.4(4) . . ?
C16 C11 N4 123.5(4) . . ?
C12 C11 N4 116.1(4) . . ?
C11 C12 C13 118.7(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 Cl1 120.5(4) . . ?
C12 C13 Cl1 119.5(4) . . ?
C13 C14 C15 122.1(4) . . ?
C13 C14 F1 119.1(4) . . ?
C15 C14 F1 118.8(4) . . ?
C14 C15 C16 119.1(5) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 119.8(5) . . ?
C11 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
O6 C17 C18 108.4(4) . . ?
O6 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O6 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 C19 111.9(4) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
N20 C19 C18 113.2(4) . . ?
N20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.8 . . ?
C21 N20 C19 110.1(3) . . ?
C21 N20 C25 108.4(3) . . ?
C19 N20 C25 111.2(4) . . ?
N20 C21 C22 110.0(4) . . ?
N20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O23 C22 C21 110.3(4) . . ?
O23 C22 H22A 109.6 . . ?
C21 C22 H22A 109.6 . . ?
O23 C22 H22B 109.6 . . ?
C21 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?
C24 O23 C22 110.5(4) . . ?
O23 C24 C25 112.5(4) . . ?
O23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
O23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
N20 C25 C24 109.4(4) . . ?
N20 C25 H25A 109.8 . . ?
C24 C25 H25A 109.8 . . ?
N20 C25 H25B 109.8 . . ?
C24 C25 H25B 109.8 . . ?
H25A C25 H25B 108.2 . . ?
O7 C26 H26A 109.5 . . ?
O7 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O7 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O43 C27 O42 121.4(4) . . ?
O43 C27 C28 122.5(4) . . ?
O42 C27 C28 116.1(4) . . ?
C29 C28 C33 118.4(4) . . ?
C29 C28 C27 119.0(4) . . ?
C33 C28 C27 122.5(4) . . ?
C30 C29 C28 122.5(4) . . ?
C30 C29 H29 118.7 . . ?
C28 C29 H29 118.7 . . ?
C29 C30 C31 118.5(4) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C32 C31 C30 120.7(4) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C33 121.6(4) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
N33 C33 C32 120.6(4) . . ?
N33 C33 C28 121.2(4) . . ?
C32 C33 C28 118.3(4) . . ?
C33 N33 C34 122.7(3) . . ?
C33 N33 H33N 117(3) . . ?
C34 N33 H33N 117(3) . . ?
C35 C34 C39 120.7(4) . . ?
C35 C34 N33 118.4(4) . . ?
C39 C34 N33 120.9(4) . . ?
C36 C35 C34 119.8(4) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 120.1(4) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C37 C38 120.9(4) . . ?
C36 C37 H37 119.5 . . ?
C38 C37 H37 119.5 . . ?
C39 C38 C37 119.3(4) . . ?
C39 C38 C40 121.0(4) . . ?
C37 C38 C40 119.8(4) . . ?
C38 C39 C34 119.2(4) . . ?
C38 C39 C41 119.9(4) . . ?
C34 C39 C41 120.9(4) . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C27 O42 H42O 115(3) . . ?
H6A O44 H6B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C2 N3 0.2(7) . . . . ?
N1 C2 N3 C4 0.5(7) . . . . ?
C2 N3 C4 N4 178.5(4) . . . . ?
C2 N3 C4 C10 -1.6(7) . . . . ?
N3 C4 N4 C11 2.8(7) . . . . ?
C10 C4 N4 C11 -177.0(4) . . . . ?
C10 C5 C6 O6 -179.5(4) . . . . ?
C10 C5 C6 C7 0.1(7) . . . . ?
C5 C6 O6 C17 -4.7(6) . . . . ?
C7 C6 O6 C17 175.7(4) . . . . ?
O6 C6 C7 O7 -1.6(6) . . . . ?
C5 C6 C7 O7 178.8(4) . . . . ?
O6 C6 C7 C8 177.9(4) . . . . ?
C5 C6 C7 C8 -1.7(7) . . . . ?
C8 C7 O7 C26 6.1(6) . . . . ?
C6 C7 O7 C26 -174.4(4) . . . . ?
O7 C7 C8 C9 -178.9(4) . . . . ?
C6 C7 C8 C9 1.7(7) . . . . ?
C2 N1 C9 C10 0.2(6) . . . . ?
C2 N1 C9 C8 -179.8(4) . . . . ?
C7 C8 C9 N1 179.9(4) . . . . ?
C7 C8 C9 C10 -0.1(7) . . . . ?
N1 C9 C10 C5 178.5(4) . . . . ?
C8 C9 C10 C5 -1.6(6) . . . . ?
N1 C9 C10 C4 -1.2(6) . . . . ?
C8 C9 C10 C4 178.7(4) . . . . ?
C6 C5 C10 C9 1.5(6) . . . . ?
C6 C5 C10 C4 -178.8(4) . . . . ?
N3 C4 C10 C9 2.0(6) . . . . ?
N4 C4 C10 C9 -178.2(4) . . . . ?
N3 C4 C10 C5 -177.7(4) . . . . ?
N4 C4 C10 C5 2.1(7) . . . . ?
C4 N4 C11 C16 36.2(7) . . . . ?
C4 N4 C11 C12 -145.8(5) . . . . ?
C16 C11 C12 C13 2.2(7) . . . . ?
N4 C11 C12 C13 -175.8(4) . . . . ?
C11 C12 C13 C14 0.0(7) . . . . ?
C11 C12 C13 Cl1 -177.3(4) . . . . ?
C12 C13 C14 C15 -1.7(8) . . . . ?
Cl1 C13 C14 C15 175.5(4) . . . . ?
C12 C13 C14 F1 178.4(4) . . . . ?
Cl1 C13 C14 F1 -4.4(6) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
F1 C14 C15 C16 -178.9(4) . . . . ?
C12 C11 C16 C15 -2.7(7) . . . . ?
N4 C11 C16 C15 175.1(5) . . . . ?
C14 C15 C16 C11 1.0(8) . . . . ?
C6 O6 C17 C18 -179.1(4) . . . . ?
O6 C17 C18 C19 -173.7(4) . . . . ?
C17 C18 C19 N20 -53.0(6) . . . . ?
C18 C19 N20 C21 171.6(4) . . . . ?
C18 C19 N20 C25 -68.3(5) . . . . ?
C19 N20 C21 C22 -178.2(4) . . . . ?
C25 N20 C21 C22 59.9(5) . . . . ?
N20 C21 C22 O23 -59.9(5) . . . . ?
C21 C22 O23 C24 56.8(5) . . . . ?
C22 O23 C24 C25 -56.7(5) . . . . ?
C21 N20 C25 C24 -58.2(5) . . . . ?
C19 N20 C25 C24 -179.4(4) . . . . ?
O23 C24 C25 N20 57.2(5) . . . . ?
O43 C27 C28 C29 167.7(4) . . . . ?
O42 C27 C28 C29 -11.1(6) . . . . ?
O43 C27 C28 C33 -7.2(7) . . . . ?
O42 C27 C28 C33 174.0(4) . . . . ?
C33 C28 C29 C30 0.5(6) . . . . ?
C27 C28 C29 C30 -174.6(4) . . . . ?
C28 C29 C30 C31 0.8(7) . . . . ?
C29 C30 C31 C32 -1.2(7) . . . . ?
C30 C31 C32 C33 0.3(7) . . . . ?
C31 C32 C33 N33 -178.8(4) . . . . ?
C31 C32 C33 C28 1.0(6) . . . . ?
C29 C28 C33 N33 178.4(4) . . . . ?
C27 C28 C33 N33 -6.7(6) . . . . ?
C29 C28 C33 C32 -1.4(6) . . . . ?
C27 C28 C33 C32 173.5(4) . . . . ?
C32 C33 N33 C34 -3.6(6) . . . . ?
C28 C33 N33 C34 176.6(4) . . . . ?
C33 N33 C34 C35 -109.7(5) . . . . ?
C33 N33 C34 C39 70.0(6) . . . . ?
C39 C34 C35 C36 -0.7(7) . . . . ?
N33 C34 C35 C36 179.0(4) . . . . ?
C34 C35 C36 C37 -1.5(7) . . . . ?
C35 C36 C37 C38 1.6(7) . . . . ?
C36 C37 C38 C39 0.5(7) . . . . ?
C36 C37 C38 C40 -179.4(4) . . . . ?
C37 C38 C39 C34 -2.5(6) . . . . ?
C40 C38 C39 C34 177.3(4) . . . . ?
C37 C38 C39 C41 177.0(4) . . . . ?
C40 C38 C39 C41 -3.1(6) . . . . ?
C35 C34 C39 C38 2.7(6) . . . . ?
N33 C34 C39 C38 -177.0(4) . . . . ?
C35 C34 C39 C41 -176.9(4) . . . . ?
N33 C34 C39 C41 3.5(6) . . . . ?

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol-acetonitrile mixture'
