# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_azoch3x2-027_sq
_database_code_depnum_ccdc_archive 'CCDC 2124206'
loop_
_audit_author_name
_audit_author_address
'Marcos Flores-Alamo'
;Facultad de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2021-11-25 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_date             2021-11-25T01:07:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H19 N3 O2'
_chemical_formula_weight         285.34
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_Int_Tables_number      5
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   16.8439(12)
_cell_length_b                   8.1225(6)
_cell_length_c                   29.795(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.644(7)
_cell_angle_gamma                90
_cell_volume                     4040.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3700
_cell_measurement_theta_min      3.649
_cell_measurement_theta_max      27.428

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    0.938
_exptl_crystal_F_000             1216
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-24 -1 11 0.1294
24 1 -11 0.1294
-1 -11 -5 0.1822
1 11 5 0.1822
4 0 40 0.0727
-4 0 -40 0.0727


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
        Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.991
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.991

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      0.001974
_diffrn_orient_matrix_ub_12      0.026279
_diffrn_orient_matrix_ub_13      -0.0225387
_diffrn_orient_matrix_ub_21      0.0372857
_diffrn_orient_matrix_ub_22      0.0385452
_diffrn_orient_matrix_ub_23      0.0072098
_diffrn_orient_matrix_ub_31      0.0202695
_diffrn_orient_matrix_ub_32      -0.0737292
_diffrn_orient_matrix_ub_33      -0.0042821
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.057
_diffrn_reflns_number            15432
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.432
_diffrn_reflns_theta_max         29.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.876
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.74
_reflns_Friedel_fraction_full    0.771
_reflns_Friedel_fraction_max     0.585
_reflns_Friedel_coverage         0.584
_reflns_number_total             8297
_reflns_number_gt                6461
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_computing_structure_refinement  
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_molecular_graphics    
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  
;	
        'WinGX publication routines (Farrugia, 1999)'				 
	L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0722P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8297
_refine_ls_number_parameters     399
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(6)
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.38458(15) 0.7586(3) 0.23767(9) 0.0275(5) Uani 1 1 d . . . . .
C2 C 0.31342(14) 0.6633(3) 0.23065(8) 0.0275(6) Uani 1 1 d . . . . .
C3 C 0.28783(15) 0.5747(4) 0.26644(9) 0.0315(6) Uani 1 1 d . . . . .
H3 H 0.240982 0.508473 0.261551 0.038 Uiso 1 1 calc R U . . .
C4 C 0.33229(15) 0.5851(4) 0.30947(9) 0.0307(6) Uani 1 1 d . . . . .
C5 C 0.40155(16) 0.6797(4) 0.31686(9) 0.0296(6) Uani 1 1 d . . . . .
H5 H 0.430387 0.687745 0.346432 0.035 Uiso 1 1 calc R U . . .
C6 C 0.42845(15) 0.7620(3) 0.28130(9) 0.0282(6) Uani 1 1 d . . . . .
C7 C 0.20731(18) 0.5491(4) 0.17913(10) 0.0438(7) Uani 1 1 d . . . . .
H7A H 0.185042 0.556474 0.147089 0.066 Uiso 1 1 calc R U . . .
H7B H 0.166469 0.581902 0.197929 0.066 Uiso 1 1 calc R U . . .
H7C H 0.224061 0.435583 0.186367 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5469(2) 0.8517(5) 0.32783(10) 0.0447(8) Uani 1 1 d . . . . .
H8A H 0.592379 0.925861 0.326449 0.067 Uiso 1 1 calc R U . . .
H8B H 0.56656 0.739533 0.334278 0.067 Uiso 1 1 calc R U . . .
H8C H 0.516438 0.888105 0.351858 0.067 Uiso 1 1 calc R U . . .
C9 C 0.41476(16) 0.9734(4) 0.13743(8) 0.0307(6) Uani 1 1 d . . . . .
C10 C 0.41804(17) 1.1454(4) 0.13591(9) 0.0358(6) Uani 1 1 d . . . . .
C11 C 0.4497(2) 1.2156(4) 0.09957(11) 0.0481(8) Uani 1 1 d . . . . .
H11 H 0.452343 1.332133 0.097444 0.058 Uiso 1 1 calc R U . . .
C12 C 0.4770(2) 1.1218(4) 0.06700(10) 0.0516(9) Uani 1 1 d . . . . .
H12 H 0.497858 1.173349 0.042431 0.062 Uiso 1 1 calc R U . . .
C13 C 0.47456(19) 0.9538(4) 0.06946(10) 0.0446(8) Uani 1 1 d . . . . .
H13 H 0.494471 0.889697 0.046732 0.054 Uiso 1 1 calc R U . . .
C14 C 0.44300(17) 0.8745(4) 0.10513(9) 0.0345(6) Uani 1 1 d . . . . .
C15 C 0.3894(2) 1.2494(4) 0.17219(13) 0.0560(9) Uani 1 1 d . . . . .
H15A H 0.33692 1.209778 0.178302 0.084 Uiso 1 1 calc R U . . .
H15B H 0.384811 1.364162 0.162065 0.084 Uiso 1 1 calc R U . . .
H15C H 0.427742 1.242023 0.1999 0.084 Uiso 1 1 calc R U . . .
C16 C 0.4404(2) 0.6887(4) 0.10760(10) 0.0451(8) Uani 1 1 d . . . . .
H16A H 0.47689 0.650738 0.133927 0.068 Uiso 1 1 calc R U . . .
H16B H 0.456776 0.641818 0.079955 0.068 Uiso 1 1 calc R U . . .
H16C H 0.385698 0.653016 0.110521 0.068 Uiso 1 1 calc R U . . .
N1 N 0.42020(13) 0.8398(3) 0.20376(7) 0.0301(5) Uani 1 1 d . . . . .
N2 N 0.37332(13) 0.9021(3) 0.17205(8) 0.0344(5) Uani 1 1 d . . . . .
N3 N 0.30572(16) 0.4999(4) 0.34459(8) 0.0435(7) Uani 1 1 d D . . . .
H3A H 0.3343(18) 0.514(5) 0.3727(8) 0.052 Uiso 1 1 d D U . . .
H3B H 0.2556(15) 0.454(4) 0.3382(11) 0.052 Uiso 1 1 d D U . . .
O1 O 0.27514(11) 0.6565(3) 0.18792(6) 0.0360(5) Uani 1 1 d . . . . .
O2 O 0.49575(11) 0.8542(3) 0.28504(6) 0.0378(5) Uani 1 1 d . . . . .
C1B C 0.80352(16) 0.8665(3) 0.18111(9) 0.0293(6) Uani 1 1 d . . . . .
C2B C 0.75834(15) 0.9630(3) 0.20804(9) 0.0292(6) Uani 1 1 d . . . . .
C3B C 0.79447(15) 1.0542(4) 0.24400(8) 0.0287(5) Uani 1 1 d . . . . .
H3BA H 0.76268 1.116964 0.261785 0.034 Uiso 1 1 calc R U . . .
C4B C 0.87819(15) 1.0547(3) 0.25444(8) 0.0286(6) Uani 1 1 d . . . . .
C5B C 0.92501(15) 0.9614(4) 0.22839(9) 0.0301(6) Uani 1 1 d . . . . .
H5B H 0.98169 0.960495 0.235472 0.036 Uiso 1 1 calc R U . . .
C6B C 0.88815(16) 0.8710(3) 0.19240(9) 0.0289(6) Uani 1 1 d . . . . .
C7B C 0.62909(16) 1.0641(4) 0.22035(11) 0.0435(7) Uani 1 1 d . . . . .
H7BA H 0.637939 1.031724 0.252316 0.065 Uiso 1 1 calc R U . . .
H7BB H 0.57239 1.049847 0.208507 0.065 Uiso 1 1 calc R U . . .
H7BC H 0.644181 1.17974 0.217508 0.065 Uiso 1 1 calc R U . . .
C8B C 1.01344(17) 0.7638(4) 0.17669(12) 0.0451(8) Uani 1 1 d . . . . .
H8BA H 1.027382 0.72225 0.207612 0.068 Uiso 1 1 calc R U . . .
H8BB H 1.036511 0.873712 0.174331 0.068 Uiso 1 1 calc R U . . .
H8BC H 1.034824 0.689209 0.155386 0.068 Uiso 1 1 calc R U . . .
C9B C 0.68475(18) 0.6364(4) 0.09618(9) 0.0374(7) Uani 1 1 d . . . . .
C10B C 0.6674(2) 0.7313(4) 0.05721(10) 0.0444(8) Uani 1 1 d . . . . .
C11B C 0.6394(2) 0.6509(5) 0.01710(11) 0.0601(10) Uani 1 1 d . . . . .
H11B H 0.627612 0.712297 -0.010104 0.072 Uiso 1 1 calc R U . . .
C12B C 0.6285(3) 0.4835(5) 0.01642(12) 0.0680(12) Uani 1 1 d . . . . .
H12B H 0.607143 0.430426 -0.010965 0.082 Uiso 1 1 calc R U . . .
C13B C 0.6482(2) 0.3921(4) 0.05517(11) 0.0537(9) Uani 1 1 d . . . . .
H13B H 0.643919 0.275579 0.053632 0.064 Uiso 1 1 calc R U . . .
C14B C 0.6739(2) 0.4652(4) 0.09585(11) 0.0469(8) Uani 1 1 d . . . . .
C15B C 0.6770(3) 0.9143(4) 0.05867(13) 0.0623(10) Uani 1 1 d . . . . .
H15D H 0.733185 0.942636 0.057363 0.093 Uiso 1 1 calc R U . . .
H15E H 0.660704 0.956718 0.086854 0.093 Uiso 1 1 calc R U . . .
H15F H 0.64334 0.963438 0.032757 0.093 Uiso 1 1 calc R U . . .
C16B C 0.6909(3) 0.3663(5) 0.13853(13) 0.0707(12) Uani 1 1 d . . . . .
H16D H 0.664177 0.417205 0.162323 0.106 Uiso 1 1 calc R U . . .
H16E H 0.748774 0.363056 0.148185 0.106 Uiso 1 1 calc R U . . .
H16F H 0.670719 0.253928 0.132978 0.106 Uiso 1 1 calc R U . . .
N1B N 0.77567(14) 0.7760(3) 0.14209(8) 0.0370(6) Uani 1 1 d . . . . .
N2B N 0.70773(15) 0.7154(3) 0.13974(8) 0.0398(6) Uani 1 1 d . . . . .
N3B N 0.91372(14) 1.1425(3) 0.29135(8) 0.0379(6) Uani 1 1 d D . . . .
H3BB H 0.9649(14) 1.184(4) 0.2894(10) 0.045 Uiso 1 1 d D U . . .
H3BC H 0.8796(17) 1.202(4) 0.3071(10) 0.045 Uiso 1 1 d D U . . .
O1B O 0.67731(10) 0.9623(3) 0.19493(6) 0.0371(5) Uani 1 1 d . . . . .
O2B O 0.92825(11) 0.7728(3) 0.16609(7) 0.0416(5) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.406(3) . ?
C1 C6 1.407(4) . ?
C1 C2 1.419(4) . ?
C2 O1 1.350(3) . ?
C2 C3 1.401(4) . ?
C3 C4 1.399(4) . ?
C3 H3 0.95 . ?
C4 N3 1.378(3) . ?
C4 C5 1.390(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.95 . ?
C6 O2 1.351(3) . ?
C7 O1 1.433(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O2 1.440(3) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C14 1.385(4) . ?
C9 C10 1.399(4) . ?
C9 N2 1.442(3) . ?
C10 C11 1.391(4) . ?
C10 C15 1.501(4) . ?
C11 C12 1.361(5) . ?
C11 H11 0.95 . ?
C12 C13 1.368(5) . ?
C12 H12 0.95 . ?
C13 C14 1.406(4) . ?
C13 H13 0.95 . ?
C14 C16 1.513(4) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
N1 N2 1.255(3) . ?
N3 H3A 0.92(2) . ?
N3 H3B 0.92(2) . ?
C1B N1B 1.403(4) . ?
C1B C2B 1.414(4) . ?
C1B C6B 1.421(4) . ?
C2B O1B 1.369(3) . ?
C2B C3B 1.376(4) . ?
C3B C4B 1.403(4) . ?
C3B H3BA 0.95 . ?
C4B N3B 1.379(3) . ?
C4B C5B 1.400(4) . ?
C5B C6B 1.378(4) . ?
C5B H5B 0.95 . ?
C6B O2B 1.359(3) . ?
C7B O1B 1.442(3) . ?
C7B H7BA 0.98 . ?
C7B H7BB 0.98 . ?
C7B H7BC 0.98 . ?
C8B O2B 1.430(3) . ?
C8B H8BA 0.98 . ?
C8B H8BB 0.98 . ?
C8B H8BC 0.98 . ?
C9B C10B 1.392(4) . ?
C9B C14B 1.402(4) . ?
C9B N2B 1.454(4) . ?
C10B C11B 1.388(5) . ?
C10B C15B 1.495(5) . ?
C11B C12B 1.371(5) . ?
C11B H11B 0.95 . ?
C12B C13B 1.376(5) . ?
C12B H12B 0.95 . ?
C13B C14B 1.367(4) . ?
C13B H13B 0.95 . ?
C14B C16B 1.499(5) . ?
C15B H15D 0.98 . ?
C15B H15E 0.98 . ?
C15B H15F 0.98 . ?
C16B H16D 0.98 . ?
C16B H16E 0.98 . ?
C16B H16F 0.98 . ?
N1B N2B 1.239(3) . ?
N3B H3BB 0.93(2) . ?
N3B H3BC 0.93(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
N1 C1 C6 115.6(2) . . ?
N1 C1 C2 125.6(2) . . ?
C6 C1 C2 118.4(2) . . ?
O1 C2 C3 122.7(2) . . ?
O1 C2 C1 116.7(2) . . ?
C3 C2 C1 120.5(2) . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N3 C4 C5 120.5(2) . . ?
N3 C4 C3 118.5(3) . . ?
C5 C4 C3 121.0(2) . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
O2 C6 C5 124.3(2) . . ?
O2 C6 C1 114.8(2) . . ?
C5 C6 C1 121.0(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 122.5(2) . . ?
C14 C9 N2 120.5(2) . . ?
C10 C9 N2 116.7(2) . . ?
C11 C10 C9 117.1(3) . . ?
C11 C10 C15 121.5(3) . . ?
C9 C10 C15 121.4(3) . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C9 C14 C13 117.3(3) . . ?
C9 C14 C16 122.0(2) . . ?
C13 C14 C16 120.7(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 N1 C1 116.4(2) . . ?
N1 N2 C9 112.6(2) . . ?
C4 N3 H3A 117(2) . . ?
C4 N3 H3B 115(2) . . ?
H3A N3 H3B 127(3) . . ?
C2 O1 C7 117.8(2) . . ?
C6 O2 C8 117.5(2) . . ?
N1B C1B C2B 127.9(2) . . ?
N1B C1B C6B 115.1(2) . . ?
C2B C1B C6B 116.7(2) . . ?
O1B C2B C3B 123.0(2) . . ?
O1B C2B C1B 115.3(2) . . ?
C3B C2B C1B 121.6(2) . . ?
C2B C3B C4B 120.1(2) . . ?
C2B C3B H3BA 120 . . ?
C4B C3B H3BA 120 . . ?
N3B C4B C5B 120.4(2) . . ?
N3B C4B C3B 119.7(2) . . ?
C5B C4B C3B 119.9(2) . . ?
C6B C5B C4B 119.4(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
O2B C6B C5B 123.7(2) . . ?
O2B C6B C1B 114.1(2) . . ?
C5B C6B C1B 122.1(2) . . ?
O1B C7B H7BA 109.5 . . ?
O1B C7B H7BB 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
O1B C7B H7BC 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
O2B C8B H8BA 109.5 . . ?
O2B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
O2B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C10B C9B C14B 122.0(3) . . ?
C10B C9B N2B 120.1(3) . . ?
C14B C9B N2B 117.6(3) . . ?
C11B C10B C9B 117.9(3) . . ?
C11B C10B C15B 121.0(3) . . ?
C9B C10B C15B 121.1(3) . . ?
C12B C11B C10B 120.6(3) . . ?
C12B C11B H11B 119.7 . . ?
C10B C11B H11B 119.7 . . ?
C11B C12B C13B 120.4(3) . . ?
C11B C12B H12B 119.8 . . ?
C13B C12B H12B 119.8 . . ?
C14B C13B C12B 121.5(3) . . ?
C14B C13B H13B 119.3 . . ?
C12B C13B H13B 119.3 . . ?
C13B C14B C9B 117.5(3) . . ?
C13B C14B C16B 121.4(3) . . ?
C9B C14B C16B 121.0(3) . . ?
C10B C15B H15D 109.5 . . ?
C10B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C10B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C14B C16B H16D 109.5 . . ?
C14B C16B H16E 109.5 . . ?
H16D C16B H16E 109.5 . . ?
C14B C16B H16F 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
N2B N1B C1B 117.4(2) . . ?
N1B N2B C9B 111.1(2) . . ?
C4B N3B H3BB 116.2(19) . . ?
C4B N3B H3BC 116(2) . . ?
H3BB N3B H3BC 119(3) . . ?
C2B O1B C7B 117.2(2) . . ?
C6B O2B C8B 117.6(2) . . ?

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
N1 C1 C2 O1 -3.1(4) . . . . ?
C6 C1 C2 O1 -176.8(2) . . . . ?
N1 C1 C2 C3 173.7(3) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
O1 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C3 C4 1.7(4) . . . . ?
C2 C3 C4 N3 178.8(3) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
N3 C4 C5 C6 178.8(3) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 O2 -178.7(2) . . . . ?
C4 C5 C6 C1 3.2(4) . . . . ?
N1 C1 C6 O2 5.0(3) . . . . ?
C2 C1 C6 O2 179.4(2) . . . . ?
N1 C1 C6 C5 -176.8(2) . . . . ?
C2 C1 C6 C5 -2.4(4) . . . . ?
C14 C9 C10 C11 1.4(4) . . . . ?
N2 C9 C10 C11 -172.8(3) . . . . ?
C14 C9 C10 C15 -178.0(3) . . . . ?
N2 C9 C10 C15 7.8(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C15 C10 C11 C12 178.9(3) . . . . ?
C10 C11 C12 C13 -0.6(6) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C10 C9 C14 C13 -1.1(4) . . . . ?
N2 C9 C14 C13 172.9(2) . . . . ?
C10 C9 C14 C16 179.0(3) . . . . ?
N2 C9 C14 C16 -7.0(4) . . . . ?
C12 C13 C14 C9 0.0(5) . . . . ?
C12 C13 C14 C16 179.9(3) . . . . ?
C6 C1 N1 N2 -149.5(2) . . . . ?
C2 C1 N1 N2 36.6(4) . . . . ?
C1 N1 N2 C9 -176.3(2) . . . . ?
C14 C9 N2 N1 79.4(3) . . . . ?
C10 C9 N2 N1 -106.2(3) . . . . ?
C3 C2 O1 C7 -2.3(4) . . . . ?
C1 C2 O1 C7 174.4(3) . . . . ?
C5 C6 O2 C8 6.9(4) . . . . ?
C1 C6 O2 C8 -174.9(3) . . . . ?
N1B C1B C2B O1B 2.5(4) . . . . ?
C6B C1B C2B O1B 176.9(2) . . . . ?
N1B C1B C2B C3B -175.8(3) . . . . ?
C6B C1B C2B C3B -1.3(4) . . . . ?
O1B C2B C3B C4B -177.3(2) . . . . ?
C1B C2B C3B C4B 0.8(4) . . . . ?
C2B C3B C4B N3B -178.1(3) . . . . ?
C2B C3B C4B C5B -0.4(4) . . . . ?
N3B C4B C5B C6B 178.2(3) . . . . ?
C3B C4B C5B C6B 0.6(4) . . . . ?
C4B C5B C6B O2B -177.9(2) . . . . ?
C4B C5B C6B C1B -1.2(4) . . . . ?
N1B C1B C6B O2B -6.3(3) . . . . ?
C2B C1B C6B O2B 178.5(2) . . . . ?
N1B C1B C6B C5B 176.7(3) . . . . ?
C2B C1B C6B C5B 1.5(4) . . . . ?
C14B C9B C10B C11B -0.7(5) . . . . ?
N2B C9B C10B C11B -174.7(3) . . . . ?
C14B C9B C10B C15B 178.0(4) . . . . ?
N2B C9B C10B C15B 3.9(5) . . . . ?
C9B C10B C11B C12B 0.7(6) . . . . ?
C15B C10B C11B C12B -178.0(4) . . . . ?
C10B C11B C12B C13B -2.6(7) . . . . ?
C11B C12B C13B C14B 4.5(7) . . . . ?
C12B C13B C14B C9B -4.3(6) . . . . ?
C12B C13B C14B C16B 176.4(4) . . . . ?
C10B C9B C14B C13B 2.4(5) . . . . ?
N2B C9B C14B C13B 176.7(3) . . . . ?
C10B C9B C14B C16B -178.3(3) . . . . ?
N2B C9B C14B C16B -4.1(5) . . . . ?
C2B C1B N1B N2B -32.2(4) . . . . ?
C6B C1B N1B N2B 153.3(3) . . . . ?
C1B N1B N2B C9B 175.6(2) . . . . ?
C10B C9B N2B N1B -70.9(4) . . . . ?
C14B C9B N2B N1B 114.7(3) . . . . ?
C3B C2B O1B C7B 0.5(4) . . . . ?
C1B C2B O1B C7B -177.7(2) . . . . ?
C5B C6B O2B C8B 0.0(4) . . . . ?
C1B C6B O2B C8B -176.9(3) . . . . ?

####################################################################### 
# 
# 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_azo4cl-114_sq-REV2
_database_code_depnum_ccdc_archive 'CCDC 2124207'
loop_
_audit_author_name
_audit_author_address
'Marcos Flores-Alamo'
;Facultad de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2022-01-14 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;

_audit_creation_date             2022-01-14T11:12:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H28 Cl4 N6 O5'
_chemical_formula_moiety         '2(C14 H13 Cl2 N3 O2), H2 O'
_chemical_formula_weight         670.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   17.9651(13)
_cell_length_b                   7.7876(4)
_cell_length_c                   23.1518(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.810(6)
_cell_angle_gamma                90
_cell_volume                     3238.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4144
_cell_measurement_theta_min      3.3423
_cell_measurement_theta_max      29.4521

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             1384
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 32 0.0492
-2 -1 -32 0.0492
0 11 -1 0.2909
0 -11 1 0.2909
-25 0 4 0.0462
25 0 -4 0.0462


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
        Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.964
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.964

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      0.0371417
_diffrn_orient_matrix_ub_12      -0.0003073
_diffrn_orient_matrix_ub_13      -0.0100044
_diffrn_orient_matrix_ub_21      -0.0133942
_diffrn_orient_matrix_ub_22      -0.004463
_diffrn_orient_matrix_ub_23      -0.0289195
_diffrn_orient_matrix_ub_31      -0.0005359
_diffrn_orient_matrix_ub_32      0.0909842
_diffrn_orient_matrix_ub_33      -0.0014359
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_number            22474
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         29.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_reflns_Friedel_coverage         0
_reflns_number_total             7803
_reflns_number_gt                5271
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_computing_structure_refinement  
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_molecular_graphics    
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  
;	
        'WinGX publication routines (Farrugia, 1999)'				 
	L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#


_refine_special_details          
;
 O1W and O2W are disordered over two sites with occupancies 0.50:0.50
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0851P)²+5.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7803
_refine_ls_number_parameters     408
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1931
_refine_ls_wR_factor_gt          0.1682
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.094

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.31739(19) 0.5691(4) 0.33889(14) 0.0231(7) Uani 1 1 d . . . . .
C2 C 0.26787(18) 0.6611(4) 0.30101(14) 0.0237(7) Uani 1 1 d . . . . .
C3 C 0.29422(19) 0.7487(4) 0.25420(14) 0.0239(7) Uani 1 1 d . . . . .
H3 H 0.260543 0.808544 0.22942 0.029 Uiso 1 1 calc R U . . .
C4 C 0.37080(19) 0.7505(4) 0.24267(14) 0.0242(7) Uani 1 1 d . . . . .
C5 C 0.42115(19) 0.6622(4) 0.27920(14) 0.0232(7) Uani 1 1 d . . . . .
H5 H 0.472809 0.660683 0.270984 0.028 Uiso 1 1 calc R U . . .
C6 C 0.39470(19) 0.5786(4) 0.32661(15) 0.0256(7) Uani 1 1 d . . . . .
C7 C 0.1446(2) 0.7595(5) 0.2811(2) 0.0426(10) Uani 1 1 d . . . . .
H7A H 0.146456 0.723153 0.240636 0.064 Uiso 1 1 calc R U . . .
H7B H 0.158882 0.880608 0.284131 0.064 Uiso 1 1 calc R U . . .
H7C H 0.093903 0.744615 0.295407 0.064 Uiso 1 1 calc R U . . .
C8 C 0.5194(2) 0.5206(5) 0.35844(18) 0.0391(9) Uani 1 1 d . . . . .
H8A H 0.534552 0.471106 0.32151 0.059 Uiso 1 1 calc R U . . .
H8B H 0.546322 0.463292 0.390107 0.059 Uiso 1 1 calc R U . . .
H8C H 0.531052 0.643579 0.358955 0.059 Uiso 1 1 calc R U . . .
C9 C 0.22422(18) 0.3462(4) 0.44912(14) 0.0250(7) Uani 1 1 d . . . . .
C10 C 0.2396(2) 0.1709(5) 0.45303(17) 0.0329(8) Uani 1 1 d . . . . .
C11 C 0.2287(2) 0.0808(5) 0.50389(18) 0.0385(9) Uani 1 1 d . . . . .
H11 H 0.24034 -0.038083 0.505931 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2010(2) 0.1645(6) 0.55151(17) 0.0397(10) Uani 1 1 d . . . . .
H12 H 0.193808 0.102827 0.586393 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1836(2) 0.3367(5) 0.54894(16) 0.0348(9) Uani 1 1 d . . . . .
H13 H 0.16429 0.394411 0.58161 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1950(2) 0.4236(4) 0.49764(15) 0.0273(7) Uani 1 1 d . . . . .
Cl1 Cl 0.27120(7) 0.06136(14) 0.39299(5) 0.0547(3) Uani 1 1 d . . . . .
Cl2 Cl 0.17255(6) 0.64049(11) 0.49431(4) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.30008(16) 0.4778(3) 0.38814(12) 0.0252(6) Uani 1 1 d . . . . .
N2 N 0.23224(17) 0.4394(4) 0.39631(12) 0.0288(6) Uani 1 1 d . . . . .
N3 N 0.39688(18) 0.8361(4) 0.19637(13) 0.0312(7) Uani 1 1 d D . . . .
H3G H 0.3645(19) 0.898(5) 0.1737(15) 0.037 Uiso 1 1 d D U . . .
H3F H 0.4471(11) 0.849(5) 0.1924(18) 0.037 Uiso 1 1 d D U . . .
O1 O 0.19510(13) 0.6570(3) 0.31504(10) 0.0295(5) Uani 1 1 d . . . . .
O2 O 0.44056(14) 0.4970(3) 0.36543(11) 0.0316(6) Uani 1 1 d . . . . .
C1B C 0.61483(18) 1.0065(4) 0.24284(14) 0.0215(7) Uani 1 1 d . . . . .
C2B C 0.68681(18) 1.0808(4) 0.23579(13) 0.0202(6) Uani 1 1 d . . . . .
C3B C 0.72124(18) 1.1679(4) 0.28036(14) 0.0219(6) Uani 1 1 d . . . . .
H3BA H 0.768237 1.220405 0.27443 0.026 Uiso 1 1 calc R U . . .
C4B C 0.68770(19) 1.1798(4) 0.33439(14) 0.0242(7) Uani 1 1 d . . . . .
C5B C 0.6154(2) 1.1188(4) 0.34206(15) 0.0272(7) Uani 1 1 d . . . . .
H5B H 0.591476 1.13225 0.378119 0.033 Uiso 1 1 calc R U . . .
C6B C 0.57898(19) 1.0384(4) 0.29632(15) 0.0247(7) Uani 1 1 d . . . . .
C7B C 0.78682(19) 1.1483(5) 0.17338(15) 0.0291(8) Uani 1 1 d . . . . .
H7BA H 0.803237 1.125334 0.133941 0.044 Uiso 1 1 calc R U . . .
H7BB H 0.824018 1.104454 0.201018 0.044 Uiso 1 1 calc R U . . .
H7BC H 0.78098 1.272362 0.178796 0.044 Uiso 1 1 calc R U . . .
C8B C 0.4670(2) 1.0207(5) 0.35038(18) 0.0415(10) Uani 1 1 d . . . . .
H8BA H 0.417094 0.970793 0.347021 0.062 Uiso 1 1 calc R U . . .
H8BB H 0.463031 1.145548 0.354757 0.062 Uiso 1 1 calc R U . . .
H8BC H 0.492857 0.972354 0.384215 0.062 Uiso 1 1 calc R U . . .
C9B C 0.55641(18) 0.7252(4) 0.13119(14) 0.0216(7) Uani 1 1 d . . . . .
C10B C 0.50837(19) 0.7862(4) 0.08796(14) 0.0242(7) Uani 1 1 d . . . . .
C11B C 0.4619(2) 0.6788(5) 0.05652(15) 0.0299(8) Uani 1 1 d . . . . .
H11B H 0.430507 0.723853 0.026826 0.036 Uiso 1 1 calc R U . . .
C12B C 0.4616(2) 0.5054(5) 0.06876(17) 0.0351(9) Uani 1 1 d . . . . .
H12B H 0.429865 0.430501 0.047368 0.042 Uiso 1 1 calc R U . . .
C13B C 0.5071(2) 0.4406(4) 0.11191(17) 0.0324(8) Uani 1 1 d . . . . .
H13B H 0.506307 0.321567 0.120826 0.039 Uiso 1 1 calc R U . . .
C14B C 0.55404(19) 0.5504(4) 0.14213(15) 0.0248(7) Uani 1 1 d . . . . .
Cl1B Cl 0.50287(6) 1.00531(11) 0.07600(4) 0.0344(2) Uani 1 1 d . . . . .
Cl2B Cl 0.61035(5) 0.46356(11) 0.19642(4) 0.0357(2) Uani 1 1 d . . . . .
N1B N 0.57537(15) 0.9004(3) 0.20541(12) 0.0212(6) Uani 1 1 d . . . . .
N2B N 0.60717(15) 0.8377(3) 0.16147(11) 0.0217(6) Uani 1 1 d . . . . .
N3B N 0.72628(18) 1.2500(4) 0.37938(13) 0.0309(7) Uani 1 1 d D . . . .
H3J H 0.701(2) 1.267(5) 0.4120(12) 0.037 Uiso 1 1 d D U . . .
H3H H 0.7705(14) 1.299(5) 0.3711(17) 0.037 Uiso 1 1 d D U . . .
O1B O 0.71728(12) 1.0650(3) 0.18269(9) 0.0224(5) Uani 1 1 d . . . . .
O2B O 0.50811(14) 0.9821(3) 0.29950(11) 0.0354(6) Uani 1 1 d . . . . .
O1W O 0.4276(3) 0.4272(7) 0.4867(2) 0.0458(11) Uani 0.497(5) 1 d G . P A 1
H1WA H 0.382784 0.450132 0.498145 0.069 Uiso 0.497(5) 1 d G U P A 1
H1WB H 0.429147 0.322925 0.473324 0.069 Uiso 0.497(5) 1 d G U P A 1
O2W O 0.3540(3) 0.7333(7) 0.5060(2) 0.0458(11) Uani 0.503(5) 1 d G . P A 2
H2WA H 0.378987 0.638508 0.510672 0.069 Uiso 0.503(5) 1 d G U P A 2
H2WB H 0.33384 0.751689 0.539417 0.069 Uiso 0.503(5) 1 d G U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.383(4) . ?
C1 C6 1.423(5) . ?
C1 C2 1.433(5) . ?
C2 O1 1.352(4) . ?
C2 C3 1.371(5) . ?
C3 C4 1.405(5) . ?
C3 H3 0.95 . ?
C4 N3 1.352(4) . ?
C4 C5 1.409(5) . ?
C5 C6 1.367(5) . ?
C5 H5 0.95 . ?
C6 O2 1.367(4) . ?
C7 O1 1.434(4) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O2 1.440(4) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C14 1.384(5) . ?
C9 C10 1.396(5) . ?
C9 N2 1.431(4) . ?
C10 C11 1.387(5) . ?
C10 Cl1 1.733(4) . ?
C11 C12 1.380(6) . ?
C11 H11 0.95 . ?
C12 C13 1.378(6) . ?
C12 H12 0.95 . ?
C13 C14 1.385(5) . ?
C13 H13 0.95 . ?
C14 Cl2 1.738(4) . ?
N1 N2 1.272(4) . ?
N3 H3G 0.915(19) . ?
N3 H3F 0.914(19) . ?
C1B N1B 1.385(4) . ?
C1B C6B 1.425(5) . ?
C1B C2B 1.428(5) . ?
C2B O1B 1.358(4) . ?
C2B C3B 1.374(4) . ?
C3B C4B 1.399(5) . ?
C3B H3BA 0.95 . ?
C4B N3B 1.358(4) . ?
C4B C5B 1.397(5) . ?
C5B C6B 1.386(5) . ?
C5B H5B 0.95 . ?
C6B O2B 1.349(4) . ?
C7B O1B 1.427(4) . ?
C7B H7BA 0.98 . ?
C7B H7BB 0.98 . ?
C7B H7BC 0.98 . ?
C8B O2B 1.431(4) . ?
C8B H8BA 0.98 . ?
C8B H8BB 0.98 . ?
C8B H8BC 0.98 . ?
C9B C14B 1.385(4) . ?
C9B C10B 1.396(4) . ?
C9B N2B 1.439(4) . ?
C10B C11B 1.382(5) . ?
C10B Cl1B 1.731(3) . ?
C11B C12B 1.380(5) . ?
C11B H11B 0.95 . ?
C12B C13B 1.378(5) . ?
C12B H12B 0.95 . ?
C13B C14B 1.384(5) . ?
C13B H13B 0.95 . ?
C14B Cl2B 1.739(3) . ?
N1B N2B 1.271(4) . ?
N3B H3J 0.893(19) . ?
N3B H3H 0.905(19) . ?
O1W H1WA 0.87 . ?
O1W H1WB 0.8702 . ?
O2W H2WA 0.87 . ?
O2W H2WB 0.87 . ?

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 C1 C6 115.0(3) . . ?
N1 C1 C2 128.1(3) . . ?
C6 C1 C2 116.8(3) . . ?
O1 C2 C3 123.2(3) . . ?
O1 C2 C1 115.8(3) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
N3 C4 C3 120.4(3) . . ?
N3 C4 C5 119.3(3) . . ?
C3 C4 C5 120.2(3) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 O2 122.4(3) . . ?
C5 C6 C1 122.4(3) . . ?
O2 C6 C1 115.2(3) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 116.7(3) . . ?
C14 C9 N2 121.1(3) . . ?
C10 C9 N2 121.9(3) . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 Cl1 118.9(3) . . ?
C9 C10 Cl1 119.8(3) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 123.1(3) . . ?
C9 C14 Cl2 118.5(3) . . ?
C13 C14 Cl2 118.4(3) . . ?
N2 N1 C1 118.1(3) . . ?
N1 N2 C9 110.8(3) . . ?
C4 N3 H3G 119(3) . . ?
C4 N3 H3F 119(3) . . ?
H3G N3 H3F 121(4) . . ?
C2 O1 C7 117.5(3) . . ?
C6 O2 C8 116.8(3) . . ?
N1B C1B C6B 114.4(3) . . ?
N1B C1B C2B 128.8(3) . . ?
C6B C1B C2B 116.7(3) . . ?
O1B C2B C3B 122.8(3) . . ?
O1B C2B C1B 116.3(3) . . ?
C3B C2B C1B 120.8(3) . . ?
C2B C3B C4B 120.6(3) . . ?
C2B C3B H3BA 119.7 . . ?
C4B C3B H3BA 119.7 . . ?
N3B C4B C5B 120.3(3) . . ?
N3B C4B C3B 119.4(3) . . ?
C5B C4B C3B 120.3(3) . . ?
C6B C5B C4B 119.1(3) . . ?
C6B C5B H5B 120.5 . . ?
C4B C5B H5B 120.5 . . ?
O2B C6B C5B 122.7(3) . . ?
O2B C6B C1B 115.4(3) . . ?
C5B C6B C1B 121.9(3) . . ?
O1B C7B H7BA 109.5 . . ?
O1B C7B H7BB 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
O1B C7B H7BC 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
O2B C8B H8BA 109.5 . . ?
O2B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
O2B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C14B C9B C10B 116.4(3) . . ?
C14B C9B N2B 122.0(3) . . ?
C10B C9B N2B 121.6(3) . . ?
C11B C10B C9B 122.3(3) . . ?
C11B C10B Cl1B 118.7(3) . . ?
C9B C10B Cl1B 118.9(2) . . ?
C12B C11B C10B 119.2(3) . . ?
C12B C11B H11B 120.4 . . ?
C10B C11B H11B 120.4 . . ?
C13B C12B C11B 120.2(3) . . ?
C13B C12B H12B 119.9 . . ?
C11B C12B H12B 119.9 . . ?
C12B C13B C14B 119.4(3) . . ?
C12B C13B H13B 120.3 . . ?
C14B C13B H13B 120.3 . . ?
C13B C14B C9B 122.3(3) . . ?
C13B C14B Cl2B 118.0(3) . . ?
C9B C14B Cl2B 119.7(3) . . ?
N2B N1B C1B 119.9(3) . . ?
N1B N2B C9B 109.5(3) . . ?
C4B N3B H3J 117(3) . . ?
C4B N3B H3H 117(3) . . ?
H3J N3B H3H 125(4) . . ?
C2B O1B C7B 117.4(2) . . ?
C6B O2B C8B 118.3(3) . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 104.5 . . ?

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
N1 C1 C2 O1 -0.5(5) . . . . ?
C6 C1 C2 O1 -177.0(3) . . . . ?
N1 C1 C2 C3 178.7(3) . . . . ?
C6 C1 C2 C3 2.2(5) . . . . ?
O1 C2 C3 C4 178.7(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 N3 179.7(3) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
N3 C4 C5 C6 178.7(3) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C4 C5 C6 O2 -176.9(3) . . . . ?
C4 C5 C6 C1 3.6(5) . . . . ?
N1 C1 C6 C5 179.2(3) . . . . ?
C2 C1 C6 C5 -3.9(5) . . . . ?
N1 C1 C6 O2 -0.3(4) . . . . ?
C2 C1 C6 O2 176.6(3) . . . . ?
C14 C9 C10 C11 -2.4(5) . . . . ?
N2 C9 C10 C11 -177.4(3) . . . . ?
C14 C9 C10 Cl1 176.3(3) . . . . ?
N2 C9 C10 Cl1 1.3(5) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
Cl1 C10 C11 C12 -177.6(3) . . . . ?
C10 C11 C12 C13 0.3(6) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C10 C9 C14 C13 2.5(5) . . . . ?
N2 C9 C14 C13 177.5(3) . . . . ?
C10 C9 C14 Cl2 -178.3(3) . . . . ?
N2 C9 C14 Cl2 -3.3(4) . . . . ?
C12 C13 C14 C9 -1.2(5) . . . . ?
C12 C13 C14 Cl2 179.6(3) . . . . ?
C6 C1 N1 N2 -168.3(3) . . . . ?
C2 C1 N1 N2 15.2(5) . . . . ?
C1 N1 N2 C9 -179.7(3) . . . . ?
C14 C9 N2 N1 105.2(4) . . . . ?
C10 C9 N2 N1 -80.0(4) . . . . ?
C3 C2 O1 C7 -4.3(5) . . . . ?
C1 C2 O1 C7 174.8(3) . . . . ?
C5 C6 O2 C8 7.6(5) . . . . ?
C1 C6 O2 C8 -172.9(3) . . . . ?
N1B C1B C2B O1B 9.5(5) . . . . ?
C6B C1B C2B O1B -173.4(3) . . . . ?
N1B C1B C2B C3B -172.6(3) . . . . ?
C6B C1B C2B C3B 4.5(4) . . . . ?
O1B C2B C3B C4B -179.7(3) . . . . ?
C1B C2B C3B C4B 2.5(5) . . . . ?
C2B C3B C4B N3B 172.8(3) . . . . ?
C2B C3B C4B C5B -6.6(5) . . . . ?
N3B C4B C5B C6B -176.1(3) . . . . ?
C3B C4B C5B C6B 3.4(5) . . . . ?
C4B C5B C6B O2B -177.3(3) . . . . ?
C4B C5B C6B C1B 4.0(5) . . . . ?
N1B C1B C6B O2B -9.1(4) . . . . ?
C2B C1B C6B O2B 173.4(3) . . . . ?
N1B C1B C6B C5B 169.7(3) . . . . ?
C2B C1B C6B C5B -7.8(5) . . . . ?
C14B C9B C10B C11B -1.4(5) . . . . ?
N2B C9B C10B C11B 176.8(3) . . . . ?
C14B C9B C10B Cl1B 174.8(3) . . . . ?
N2B C9B C10B Cl1B -7.0(4) . . . . ?
C9B C10B C11B C12B 1.3(5) . . . . ?
Cl1B C10B C11B C12B -175.0(3) . . . . ?
C10B C11B C12B C13B 0.1(6) . . . . ?
C11B C12B C13B C14B -1.1(6) . . . . ?
C12B C13B C14B C9B 0.9(6) . . . . ?
C12B C13B C14B Cl2B 179.8(3) . . . . ?
C10B C9B C14B C13B 0.4(5) . . . . ?
N2B C9B C14B C13B -177.8(3) . . . . ?
C10B C9B C14B Cl2B -178.5(3) . . . . ?
N2B C9B C14B Cl2B 3.3(5) . . . . ?
C6B C1B N1B N2B -167.1(3) . . . . ?
C2B C1B N1B N2B 10.0(5) . . . . ?
C1B N1B N2B C9B 177.0(3) . . . . ?
C14B C9B N2B N1B -92.7(4) . . . . ?
C10B C9B N2B N1B 89.1(4) . . . . ?
C3B C2B O1B C7B -2.1(4) . . . . ?
C1B C2B O1B C7B 175.8(3) . . . . ?
C5B C6B O2B C8B 5.7(5) . . . . ?
C1B C6B O2B C8B -175.5(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
C11 H11 Cl2 0.95 2.79 3.580(4) 140.6 1_545 yes
C13 H13 O1B 0.95 2.53 3.239(4) 131.1 4_576 yes
N3 H3G N2 0.915(19) 2.38(2) 3.239(4) 156(4) 2 yes
N3 H3G O1 0.915(19) 2.30(3) 3.006(4) 134(3) 2 yes
C7B H7BB Cl2B 0.98 2.86 3.796(4) 161.2 2_655 yes
C8B H8BA Cl1 0.98 2.93 3.681(4) 134.3 1_565 yes
C13B H13B Cl1B 0.95 2.67 3.491(3) 144.6 1_545 yes
N3B H3H N2B 0.905(19) 2.35(2) 3.224(4) 161(4) 2_655 yes
N3B H3H O1B 0.905(19) 2.43(4) 3.025(4) 124(3) 2_655 yes





# END of CIF
