# 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. 
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#######################################################################

data_dcf_imi_12
_database_code_depnum_ccdc_archive 'CCDC 1864780'
loop_
_audit_author_name
_audit_author_address
'Cecilia Silva'
;UFSCar
Brazil
;
_audit_update_record             
;
2019-05-23 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 Cl2 N O2, C3 H5 N2, H2 O'
_chemical_formula_sum            'C17 H17 Cl2 N3 O3'
_chemical_formula_weight         382.23
_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'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   18.9975(9)
_cell_length_b                   9.0067(4)
_cell_length_c                   10.9126(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.275(2)
_cell_angle_gamma                90
_cell_volume                     1792.37(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19634
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.393
_cell_measurement_theta_min      2.983
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.473
_exptl_crystal_size_mid          0.384
_exptl_crystal_size_min          0.114
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19634
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.393
_diffrn_reflns_theta_min         2.983
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2613
_reflns_number_total             3656
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.414
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.9198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1351
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1WA) = Uanis(O1W)
3. Rigid body (RIGU) restrains
 C15, C16, N3, C17, N2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N2, C17, N3, C16, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O1W(0.85) H1WA(0.85) H1WB(0.85) O1WA(0.15) H1WC(0.15) H1WD(0.15)
5.a Riding coordinates:
 O1WA(H1WC,H1WD)
5.b Free rotating group:
 O1W(H1WA,H1WB)
5.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
5.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C4(H4), N1(H1), C11(H11), C7(H7), C5(H5), N2(H2), C6(H6), C12(H12),
 N3(H3), C17(H17), C15(H15), C16(H16)
;
_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
Cl2 Cl 0.46503(4) 0.54250(7) 0.20718(7) 0.0532(2) Uani 1 1 d . . . . .
Cl1 Cl 0.24401(4) 0.29156(8) 0.35915(7) 0.0611(2) Uani 1 1 d . . . . .
C9 C 0.35709(12) 0.4189(2) 0.2930(2) 0.0387(5) Uani 1 1 d . . . . .
C3 C 0.26582(12) 0.7102(3) 0.0651(2) 0.0413(5) Uani 1 1 d . . . . .
C13 C 0.48371(13) 0.3542(3) 0.4030(2) 0.0474(6) Uani 1 1 d . . . . .
H13 H 0.533504 0.366938 0.412291 0.057 Uiso 1 1 calc R . . . .
C4 C 0.26797(14) 0.8639(3) 0.0501(3) 0.0533(7) Uani 1 1 d . . . . .
H4 H 0.242307 0.906053 -0.027367 0.064 Uiso 1 1 calc R . . . .
N1 N 0.30479(11) 0.4942(2) 0.1982(2) 0.0447(5) Uani 1 1 d . . . . .
H1 H 0.270561 0.443756 0.146812 0.067 Uiso 1 1 calc R . . . .
C10 C 0.33697(13) 0.3180(2) 0.3751(2) 0.0424(5) Uani 1 1 d . . . . .
C11 C 0.38693(14) 0.2398(3) 0.4675(2) 0.0493(6) Uani 1 1 d . . . . .
H11 H 0.370962 0.174028 0.519718 0.059 Uiso 1 1 calc R . . . .
C8 C 0.30557(12) 0.6506(3) 0.1829(2) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.14775(11) 0.5200(3) 0.0807(2) 0.0783(7) Uani 1 1 d . . . . .
C7 C 0.34401(13) 0.7429(3) 0.2802(3) 0.0465(6) Uani 1 1 d . . . . .
H7 H 0.369389 0.702394 0.358557 0.056 Uiso 1 1 calc R . . . .
C14 C 0.43255(13) 0.4310(2) 0.3090(2) 0.0411(5) Uani 1 1 d . . . . .
O1 O 0.10200(12) 0.5274(4) -0.1237(2) 0.1182(12) Uani 1 1 d . . . . .
C1 C 0.15229(14) 0.5516(3) -0.0260(3) 0.0512(6) Uani 1 1 d . . . . .
C5 C 0.30725(16) 0.9554(3) 0.1473(3) 0.0605(8) Uani 1 1 d . . . . .
H5 H 0.308006 1.057486 0.134717 0.073 Uiso 1 1 calc R . . . .
N2 N 0.08052(13) 0.9890(4) -0.0647(3) 0.0759(8) Uani 1 1 d . U . . .
H2 H 0.070450 0.953640 -0.140812 0.114 Uiso 1 1 calc R . . . .
C2 C 0.22332(13) 0.6140(3) -0.0426(2) 0.0474(6) Uani 1 1 d . . . . .
H2A H 0.254291 0.531864 -0.052499 0.057 Uiso 1 1 calc R . . . .
H2B H 0.212027 0.671602 -0.120779 0.057 Uiso 1 1 calc R . . . .
C6 C 0.34502(14) 0.8948(3) 0.2621(3) 0.0550(7) Uani 1 1 d . . . . .
H6 H 0.371336 0.955785 0.327752 0.066 Uiso 1 1 calc R . . . .
C12 C 0.46085(15) 0.2589(3) 0.4829(3) 0.0525(6) Uani 1 1 d . . . . .
H12 H 0.495045 0.207759 0.546655 0.063 Uiso 1 1 calc R . . . .
N3 N 0.10458(14) 1.0098(5) 0.1373(2) 0.0835(9) Uani 1 1 d . U . . .
H3 H 0.113085 0.991743 0.217486 0.125 Uiso 1 1 calc R . . . .
C17 C 0.08751(17) 0.9091(5) 0.0425(4) 0.0800(10) Uani 1 1 d . U . . .
H17 H 0.081814 0.807164 0.049327 0.096 Uiso 1 1 calc R . . . .
C15 C 0.0916(2) 1.1305(6) -0.0336(6) 0.1084(14) Uani 1 1 d . U . . .
H15 H 0.089146 1.207999 -0.090921 0.130 Uiso 1 1 calc R . . . .
C16 C 0.1059(2) 1.1440(6) 0.0835(6) 0.1119(15) Uani 1 1 d . U . . .
H16 H 0.116011 1.233222 0.127828 0.134 Uiso 1 1 calc R . . . .
O1W O 0.03825(15) 0.5765(5) 0.1834(2) 0.0876(9) Uani 0.85 1 d . . P A 1
H1WA H -0.004770 0.545512 0.146734 0.131 Uiso 0.85 1 d G . P A 1
H1WB H 0.062890 0.555607 0.131542 0.131 Uiso 0.85 1 d G . P A 1
O1WA O 0.0432(9) 0.440(2) 0.1846(15) 0.0876(9) Uani 0.15 1 d . . P B 2
H1WC H 0.067042 0.482184 0.139055 0.131 Uiso 0.15 1 d R . P B 2
H1WD H -0.001568 0.453064 0.143685 0.131 Uiso 0.15 1 d R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C14 1.734(2) . ?
Cl1 C10 1.742(2) . ?
C9 N1 1.393(3) . ?
C9 C10 1.402(3) . ?
C9 C14 1.399(3) . ?
C3 C4 1.396(3) . ?
C3 C8 1.403(3) . ?
C3 C2 1.501(3) . ?
C13 C14 1.385(3) . ?
C13 C12 1.377(4) . ?
C4 C5 1.385(4) . ?
N1 C8 1.419(3) . ?
C10 C11 1.370(4) . ?
C11 C12 1.378(4) . ?
C8 C7 1.385(3) . ?
O2 C1 1.225(3) . ?
C7 C6 1.383(4) . ?
O1 C1 1.235(3) . ?
C1 C2 1.519(3) . ?
C5 C6 1.371(4) . ?
N2 C17 1.347(5) . ?
N2 C15 1.320(6) . ?
N3 C17 1.345(5) . ?
N3 C16 1.347(6) . ?
C15 C16 1.236(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
N1 C9 C10 121.6(2) . . ?
N1 C9 C14 123.2(2) . . ?
C14 C9 C10 115.1(2) . . ?
C4 C3 C8 117.5(2) . . ?
C4 C3 C2 120.5(2) . . ?
C8 C3 C2 122.0(2) . . ?
C12 C13 C14 120.0(2) . . ?
C5 C4 C3 121.8(3) . . ?
C9 N1 C8 122.81(19) . . ?
C9 C10 Cl1 118.38(18) . . ?
C11 C10 Cl1 118.48(18) . . ?
C11 C10 C9 123.1(2) . . ?
C10 C11 C12 119.9(2) . . ?
C3 C8 N1 117.8(2) . . ?
C7 C8 C3 120.4(2) . . ?
C7 C8 N1 121.7(2) . . ?
C6 C7 C8 120.6(3) . . ?
C9 C14 Cl2 120.09(19) . . ?
C13 C14 Cl2 117.54(18) . . ?
C13 C14 C9 122.4(2) . . ?
O2 C1 O1 122.4(2) . . ?
O2 C1 C2 120.0(2) . . ?
O1 C1 C2 117.4(2) . . ?
C6 C5 C4 119.6(2) . . ?
C15 N2 C17 108.8(4) . . ?
C3 C2 C1 114.9(2) . . ?
C5 C6 C7 120.0(3) . . ?
C13 C12 C11 119.5(2) . . ?
C17 N3 C16 107.5(4) . . ?
N3 C17 N2 104.5(3) . . ?
C16 C15 N2 109.5(5) . . ?
C15 C16 N3 109.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
