# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
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data_ICB68
_database_code_depnum_ccdc_archive 'CCDC 1979548'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2018-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        ICB68
_chemical_formula_moiety         'Cl, C21 H23 F3 N5 O'
_chemical_formula_sum            'C21 H23 Cl F3 N5 O'
_chemical_formula_weight         453.89
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.0699(4)
_cell_length_b                   23.3590(9)
_cell_length_c                   16.6594(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.992(2)
_cell_angle_gamma                90
_cell_volume                     4275.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7537
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      3.27
_cell_measurement_theta_min      66.59
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.022
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.051
_exptl_crystal_size_min          0.025
_exptl_special_details           ?
_exptl_transmission_factor_max   1
_exptl_transmission_factor_min   0.823
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34141
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         3.274
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5627
_reflns_number_total             7537
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2017)'
_computing_structure_solution    'ShelXT (Sheldrick, 2014)'
_refine_diff_density_max         0.832
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         7537
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0532
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0831P)²+2.9657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1593
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C28(H28A,H28B), C32(H32A,H32B), C36(H36A,H36B), C39(H39A,
 H39B), C40(H40A,H40B), C42(H42A,H42B), C46(H46A,H46B), C50(H50A,H50B),
 C53(H53A,H53B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N9(H9), C10(H10), N10(H10A), C17(H17), C19(H19), N2(H2), C22(H22),
 C24(H24), C30(H30), C37(H37), C44(H44), C45(H45), C49(H49), C52(H52), C55(H55),
  C56(H56), C59(H59)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30360(5) 0.18884(3) 0.94063(4) 0.02598(17) Uani 1 1 d . . . . .
Cl2 Cl 0.80605(5) 0.18334(3) 0.93032(4) 0.02564(17) Uani 1 1 d . . . . .
O1 O 0.56555(16) 0.26682(8) 0.64365(11) 0.0262(4) Uani 1 1 d . . . . .
O2 O 1.08126(16) 0.26547(8) 0.64014(11) 0.0260(4) Uani 1 1 d . . . . .
N1 N 0.87900(18) 0.25037(9) 0.78655(13) 0.0220(4) Uani 1 1 d . . . . .
H1 H 0.8479 0.2326 0.8259 0.026 Uiso 1 1 calc R . . . .
N9 N 0.36616(18) 0.25387(9) 0.79177(13) 0.0222(4) Uani 1 1 d . . . . .
H9 H 0.3355 0.2364 0.8315 0.027 Uiso 1 1 calc R . . . .
N5 N 0.60789(18) 0.36196(9) 0.85932(13) 0.0207(4) Uani 1 1 d . . . . .
F8 F -0.31926(17) 0.43224(9) 1.07966(12) 0.0532(5) Uani 1 1 d . . . . .
F10 F 0.18621(17) 0.42810(9) 1.06901(12) 0.0509(5) Uani 1 1 d . . . . .
C8 C 0.5787(3) 0.31292(11) 0.58771(17) 0.0279(6) Uani 1 1 d . . . . .
H8A H 0.5032 0.3170 0.5507 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.6462 0.3044 0.5566 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.5955 0.3487 0.6178 0.042 Uiso 1 1 calc GR . . . .
N8 N 0.09388(19) 0.36479(9) 0.86369(14) 0.0232(5) Uani 1 1 d . . . . .
C10 C 0.3974(2) 0.31924(11) 0.69787(16) 0.0229(5) Uani 1 1 d . . . . .
H10 H 0.3897 0.3528 0.6655 0.027 Uiso 1 1 calc R . . . .
N7 N 0.1071(2) 0.40577(9) 0.80680(14) 0.0264(5) Uani 1 1 d . . . . .
N10 N 0.50071(19) 0.14692(9) 0.82755(14) 0.0259(5) Uani 1 1 d . . . . .
H10A H 0.4402 0.1560 0.8549 0.031 Uiso 1 1 calc R . . . .
N6 N 0.1912(2) 0.38814(9) 0.76441(14) 0.0269(5) Uani 1 1 d . . . . .
N3 N 0.70504(19) 0.38473(9) 0.75977(14) 0.0259(5) Uani 1 1 d . . . . .
N4 N 0.6219(2) 0.40294(9) 0.80251(14) 0.0262(5) Uani 1 1 d . . . . .
C16 C 0.9936(2) 0.27166(11) 0.68839(16) 0.0229(5) Uani 1 1 d . . . . .
C17 C 0.5222(2) 0.18196(11) 0.77012(16) 0.0245(5) Uani 1 1 d . . . . .
H17 H 0.5848 0.1719 0.7384 0.029 Uiso 1 1 calc R . . . .
C18 C 0.5407(3) -0.00651(12) 0.89975(19) 0.0334(6) Uani 1 1 d . . . . .
H18A H 0.5879 0.0013 0.9530 0.040 Uiso 1 1 calc R . . . .
H18B H 0.4801 -0.0366 0.9073 0.040 Uiso 1 1 calc R . . . .
C19 C 0.9097(2) 0.31576(10) 0.69258(16) 0.0227(5) Uani 1 1 d . . . . .
H19 H 0.9007 0.3491 0.6597 0.027 Uiso 1 1 calc R . . . .
C20 C 1.0937(2) 0.31223(12) 0.58505(17) 0.0277(6) Uani 1 1 d . . . . .
H20A H 1.0179 0.3166 0.5485 0.041 Uiso 1 1 calc GR . . . .
H20B H 1.1608 0.3042 0.5534 0.041 Uiso 1 1 calc GR . . . .
H20C H 1.1107 0.3477 0.6158 0.041 Uiso 1 1 calc GR . . . .
N2 N 1.01767(19) 0.14335(9) 0.82304(14) 0.0252(5) Uani 1 1 d . . . . .
H2 H 0.9561 0.1501 0.8505 0.030 Uiso 1 1 calc R . . . .
C22 C 0.6841(2) 0.31745(10) 0.85196(15) 0.0212(5) Uani 1 1 d . . . . .
H22 H 0.6929 0.2836 0.8837 0.025 Uiso 1 1 calc R . . . .
C23 C 0.9749(2) 0.23023(11) 0.74742(16) 0.0227(5) Uani 1 1 d . . . . .
C24 C 1.0391(2) 0.18001(11) 0.76682(16) 0.0238(5) Uani 1 1 d . . . . .
H24 H 1.1043 0.1714 0.7367 0.029 Uiso 1 1 calc R . . . .
C25 C 0.0089(2) 0.37208(11) 0.92072(16) 0.0227(5) Uani 1 1 d . . . . .
C26 C 0.4794(2) 0.27421(11) 0.69274(16) 0.0227(5) Uani 1 1 d . . . . .
C27 C 0.4601(2) 0.23310(11) 0.75184(16) 0.0236(5) Uani 1 1 d . . . . .
C28 C 1.0772(3) 0.07403(12) 0.92898(17) 0.0291(6) Uani 1 1 d . . . . .
H28A H 0.9899 0.0680 0.9340 0.035 Uiso 1 1 calc R . . . .
H28B H 1.1074 0.1053 0.9663 0.035 Uiso 1 1 calc R . . . .
C29 C 1.0915(2) 0.09133(11) 0.84280(17) 0.0264(6) Uani 1 1 d . . . . .
H29 H 1.1789 0.1009 0.8399 0.032 Uiso 1 1 calc R . . . .
C30 C 0.1721(2) 0.32114(11) 0.85700(16) 0.0237(5) Uani 1 1 d . . . . .
H30 H 0.1824 0.2875 0.8892 0.028 Uiso 1 1 calc R . . . .
C31 C 0.5673(2) 0.09347(11) 0.85174(17) 0.0250(5) Uani 1 1 d . . . . .
H31 H 0.6209 0.1010 0.9034 0.030 Uiso 1 1 calc R . . . .
C32 C 1.0550(2) 0.04325(12) 0.78357(18) 0.0295(6) Uani 1 1 d . . . . .
H32A H 1.0696 0.0552 0.7286 0.035 Uiso 1 1 calc R . . . .
H32B H 0.9670 0.0353 0.7826 0.035 Uiso 1 1 calc R . . . .
F2 F 0.2266(2) 0.34521(9) 1.11400(15) 0.0643(7) Uani 1 1 d . . . . .
F1 F 0.33827(18) 0.41449(15) 1.15811(14) 0.0901(10) Uani 1 1 d . . . . .
F5 F -0.2752(3) 0.35003(10) 1.12520(18) 0.0870(10) Uani 1 1 d . . . . .
C36 C 0.6469(2) 0.07323(11) 0.78955(17) 0.0279(6) Uani 1 1 d . . . . .
H36A H 0.7068 0.1033 0.7804 0.033 Uiso 1 1 calc R . . . .
H36B H 0.5962 0.0655 0.7376 0.033 Uiso 1 1 calc R . . . .
C37 C -0.0173(2) 0.32672(11) 0.96888(17) 0.0275(6) Uani 1 1 d . . . . .
H37 H 0.0182 0.2902 0.9625 0.033 Uiso 1 1 calc R . . . .
C38 C 0.3294(2) 0.30495(11) 0.76010(16) 0.0229(5) Uani 1 1 d . . . . .
C39 C 1.1476(3) 0.01917(12) 0.95278(18) 0.0339(6) Uani 1 1 d . . . . .
H39A H 1.2359 0.0268 0.9552 0.041 Uiso 1 1 calc R . . . .
H39B H 1.1309 0.0072 1.0073 0.041 Uiso 1 1 calc R . . . .
C40 C 0.6256(3) -0.02781(12) 0.84170(19) 0.0340(6) Uani 1 1 d . . . . .
H40A H 0.5770 -0.0414 0.7915 0.041 Uiso 1 1 calc R . . . .
H40B H 0.6729 -0.0607 0.8663 0.041 Uiso 1 1 calc R . . . .
C41 C -0.1479(2) 0.38821(12) 1.03555(17) 0.0281(6) Uani 1 1 d . . . . .
C42 C 0.4744(2) 0.04823(12) 0.86805(18) 0.0308(6) Uani 1 1 d . . . . .
H42A H 0.4205 0.0397 0.8176 0.037 Uiso 1 1 calc R . . . .
H42B H 0.4234 0.0627 0.9085 0.037 Uiso 1 1 calc R . . . .
C43 C 0.2332(2) 0.33609(11) 0.79351(16) 0.0231(5) Uani 1 1 d . . . . .
C44 C 0.4121(2) 0.33087(12) 1.01870(17) 0.0282(6) Uani 1 1 d . . . . .
H44 H 0.3915 0.2995 1.0507 0.034 Uiso 1 1 calc R . . . .
C45 C -0.0458(3) 0.42522(12) 0.92704(18) 0.0309(6) Uani 1 1 d . . . . .
H45 H -0.0299 0.4557 0.8921 0.037 Uiso 1 1 calc R . . . .
C46 C 0.7131(2) 0.01860(12) 0.82067(19) 0.0314(6) Uani 1 1 d . . . . .
H46A H 0.7613 0.0039 0.7788 0.038 Uiso 1 1 calc R . . . .
H46B H 0.7702 0.0278 0.8694 0.038 Uiso 1 1 calc R . . . .
C47 C 0.5222(2) 0.36938(11) 0.91572(16) 0.0221(5) Uani 1 1 d . . . . .
C48 C 0.3608(2) 0.38436(12) 1.02783(16) 0.0268(6) Uani 1 1 d . . . . .
C49 C 0.4934(2) 0.32349(11) 0.96254(17) 0.0258(6) Uani 1 1 d . . . . .
H49 H 0.5293 0.2871 0.9562 0.031 Uiso 1 1 calc R . . . .
C50 C 1.1276(3) -0.01124(12) 0.8072(2) 0.0343(7) Uani 1 1 d . . . . .
H50A H 1.0990 -0.0425 0.7695 0.041 Uiso 1 1 calc R . . . .
H50B H 1.2148 -0.0044 0.8027 0.041 Uiso 1 1 calc R . . . .
F4 F -0.1647(2) 0.42003(16) 1.16609(14) 0.0913(10) Uani 1 1 d . . . . .
C52 C 0.3881(3) 0.43005(12) 0.97919(18) 0.0310(6) Uani 1 1 d . . . . .
H52 H 0.3511 0.4663 0.9848 0.037 Uiso 1 1 calc R . . . .
C53 C 1.1131(3) -0.02911(12) 0.8931(2) 0.0376(7) Uani 1 1 d . . . . .
H53A H 1.1653 -0.0628 0.9082 0.045 Uiso 1 1 calc R . . . .
H53B H 1.0275 -0.0404 0.8961 0.045 Uiso 1 1 calc R . . . .
C54 C 0.8415(2) 0.30102(11) 0.75490(16) 0.0224(5) Uani 1 1 d . . . . .
C55 C -0.1238(3) 0.43301(12) 0.98488(19) 0.0349(7) Uani 1 1 d . . . . .
H55 H -0.1612 0.4692 0.9901 0.042 Uiso 1 1 calc R . . . .
C56 C 0.4686(2) 0.42273(12) 0.92278(17) 0.0286(6) Uani 1 1 d . . . . .
H56 H 0.4871 0.4537 0.8893 0.034 Uiso 1 1 calc R . . . .
C57 C -0.2251(2) 0.39828(13) 1.10167(18) 0.0332(6) Uani 1 1 d . . . . .
C58 C 0.7458(2) 0.33225(11) 0.78851(16) 0.0227(5) Uani 1 1 d . . . . .
C59 C -0.0959(2) 0.33494(12) 1.02649(18) 0.0302(6) Uani 1 1 d . . . . .
H59 H -0.1142 0.3040 1.0599 0.036 Uiso 1 1 calc R . . . .
C60 C 0.2795(2) 0.39382(13) 1.09224(18) 0.0316(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.443(3) . ?
O1 C26 1.341(3) . ?
O2 C16 1.341(3) . ?
O2 C20 1.444(3) . ?
N1 C23 1.393(3) . ?
N1 C54 1.341(3) . ?
N9 C27 1.388(3) . ?
N9 C38 1.348(3) . ?
N5 N4 1.368(3) . ?
N5 C22 1.354(3) . ?
N5 C47 1.425(3) . ?
F8 C57 1.325(3) . ?
F10 C60 1.327(3) . ?
N8 N7 1.367(3) . ?
N8 C25 1.426(3) . ?
N8 C30 1.351(3) . ?
C10 C26 1.399(4) . ?
C10 C38 1.394(3) . ?
N7 N6 1.302(3) . ?
N10 C17 1.303(3) . ?
N10 C31 1.481(3) . ?
N6 C43 1.369(3) . ?
N3 N4 1.302(3) . ?
N3 C58 1.372(3) . ?
C16 C19 1.394(4) . ?
C16 C23 1.413(4) . ?
C17 C27 1.393(4) . ?
C18 C40 1.513(4) . ?
C18 C42 1.536(4) . ?
C19 C54 1.399(3) . ?
N2 C24 1.312(3) . ?
N2 C29 1.479(3) . ?
C22 C58 1.370(3) . ?
C23 C24 1.389(4) . ?
C25 C37 1.381(4) . ?
C25 C45 1.391(4) . ?
C26 C27 1.410(4) . ?
C28 C29 1.518(4) . ?
C28 C39 1.527(4) . ?
C29 C32 1.517(4) . ?
C30 C43 1.368(4) . ?
C31 C36 1.515(3) . ?
C31 C42 1.522(4) . ?
C32 C50 1.531(4) . ?
F2 C60 1.347(4) . ?
F1 C60 1.299(4) . ?
F5 C57 1.335(4) . ?
C36 C46 1.530(4) . ?
C37 C59 1.385(4) . ?
C38 C43 1.455(3) . ?
C39 C53 1.521(4) . ?
C40 C46 1.522(4) . ?
C41 C55 1.391(4) . ?
C41 C57 1.493(4) . ?
C41 C59 1.387(4) . ?
C44 C48 1.388(4) . ?
C44 C49 1.386(4) . ?
C45 C55 1.381(4) . ?
C47 C49 1.385(4) . ?
C47 C56 1.391(4) . ?
C48 C52 1.395(4) . ?
C48 C60 1.499(4) . ?
C50 C53 1.518(5) . ?
F4 C57 1.297(4) . ?
C52 C56 1.383(4) . ?
C54 C58 1.454(3) . ?

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
C26 O1 C8 115.64(19) . . ?
C16 O2 C20 115.54(19) . . ?
C54 N1 C23 109.3(2) . . ?
C38 N9 C27 109.3(2) . . ?
N4 N5 C47 120.8(2) . . ?
C22 N5 N4 110.51(19) . . ?
C22 N5 C47 128.7(2) . . ?
N7 N8 C25 120.9(2) . . ?
C30 N8 N7 110.3(2) . . ?
C30 N8 C25 128.8(2) . . ?
C38 C10 C26 106.2(2) . . ?
N6 N7 N8 107.3(2) . . ?
C17 N10 C31 126.9(2) . . ?
N7 N6 C43 108.9(2) . . ?
N4 N3 C58 109.0(2) . . ?
N3 N4 N5 107.3(2) . . ?
O2 C16 C19 130.1(2) . . ?
O2 C16 C23 121.4(2) . . ?
C19 C16 C23 108.4(2) . . ?
N10 C17 C27 124.7(2) . . ?
C40 C18 C42 111.2(2) . . ?
C16 C19 C54 106.2(2) . . ?
C24 N2 C29 123.5(2) . . ?
N5 C22 C58 104.5(2) . . ?
N1 C23 C16 106.2(2) . . ?
C24 C23 N1 125.0(2) . . ?
C24 C23 C16 128.8(2) . . ?
N2 C24 C23 125.9(2) . . ?
C37 C25 N8 119.9(2) . . ?
C37 C25 C45 121.1(2) . . ?
C45 C25 N8 119.1(2) . . ?
O1 C26 C10 130.5(2) . . ?
O1 C26 C27 121.2(2) . . ?
C10 C26 C27 108.4(2) . . ?
N9 C27 C17 125.0(2) . . ?
N9 C27 C26 106.4(2) . . ?
C17 C27 C26 128.6(2) . . ?
C29 C28 C39 111.1(2) . . ?
N2 C29 C28 108.1(2) . . ?
N2 C29 C32 111.6(2) . . ?
C32 C29 C28 111.6(2) . . ?
N8 C30 C43 104.7(2) . . ?
N10 C31 C36 112.9(2) . . ?
N10 C31 C42 108.0(2) . . ?
C36 C31 C42 111.5(2) . . ?
C29 C32 C50 111.0(2) . . ?
C31 C36 C46 108.8(2) . . ?
C25 C37 C59 119.4(2) . . ?
N9 C38 C10 109.8(2) . . ?
N9 C38 C43 119.6(2) . . ?
C10 C38 C43 130.7(2) . . ?
C53 C39 C28 111.9(3) . . ?
C18 C40 C46 112.0(2) . . ?
C55 C41 C57 119.9(2) . . ?
C59 C41 C55 119.8(2) . . ?
C59 C41 C57 120.3(2) . . ?
C31 C42 C18 109.5(2) . . ?
N6 C43 C38 122.8(2) . . ?
C30 C43 N6 108.8(2) . . ?
C30 C43 C38 128.5(2) . . ?
C49 C44 C48 119.6(2) . . ?
C55 C45 C25 119.0(3) . . ?
C40 C46 C36 112.4(2) . . ?
C49 C47 N5 119.6(2) . . ?
C49 C47 C56 121.1(2) . . ?
C56 C47 N5 119.3(2) . . ?
C44 C48 C52 120.3(2) . . ?
C44 C48 C60 120.0(2) . . ?
C52 C48 C60 119.6(2) . . ?
C47 C49 C44 119.8(2) . . ?
C53 C50 C32 111.0(2) . . ?
C56 C52 C48 120.2(2) . . ?
C50 C53 C39 111.4(2) . . ?
N1 C54 C19 109.9(2) . . ?
N1 C54 C58 119.8(2) . . ?
C19 C54 C58 130.3(2) . . ?
C45 C55 C41 120.4(3) . . ?
C52 C56 C47 119.0(2) . . ?
F8 C57 F5 104.2(2) . . ?
F8 C57 C41 113.1(2) . . ?
F5 C57 C41 112.3(3) . . ?
F4 C57 F8 107.7(3) . . ?
F4 C57 F5 106.1(3) . . ?
F4 C57 C41 112.8(2) . . ?
N3 C58 C54 122.5(2) . . ?
C22 C58 N3 108.7(2) . . ?
C22 C58 C54 128.7(2) . . ?
C37 C59 C41 120.2(3) . . ?
F10 C60 F2 103.8(2) . . ?
F10 C60 C48 113.2(2) . . ?
F2 C60 C48 112.8(2) . . ?
F1 C60 F10 108.3(3) . . ?
F1 C60 F2 106.0(3) . . ?
F1 C60 C48 112.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MM34
_database_code_depnum_ccdc_archive 'CCDC 1979549'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        MM34
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 Cl N5 O, C4 H10 O, Cl, H2 O'
_chemical_formula_sum            'C24 H35 Cl2 N5 O3'
_chemical_formula_weight         512.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9219(2)
_cell_length_b                   9.5881(2)
_cell_length_c                   19.0533(5)
_cell_angle_alpha                99.4900(12)
_cell_angle_beta                 91.0584(12)
_cell_angle_gamma                110.6256(11)
_cell_volume                     1331.31(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4815
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      67.72

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   0.822
_exptl_transmission_factor_max   1
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.469
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS-2016
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17573
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         67.723
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4815
_reflns_number_gt                4232
_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       ?
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0344P)²+0.5458P] 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         4815
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
C1 C -0.5384(2) 0.10295(19) 0.21157(9) 0.0186(3) Uani 1 1 d . . . . .
C2 C -0.4212(2) 0.23653(19) 0.25306(9) 0.0200(3) Uani 1 1 d . . . . .
H2 H -0.381349 0.327843 0.234504 0.024 Uiso 1 1 calc R U . . .
C3 C -0.3631(2) 0.23491(19) 0.32186(9) 0.0192(3) Uani 1 1 d . . . . .
H3 H -0.282772 0.325043 0.351084 0.023 Uiso 1 1 calc R U . . .
C4 C -0.4238(2) 0.09953(18) 0.34753(8) 0.0168(3) Uani 1 1 d . . . . .
C5 C -0.5443(2) -0.03320(18) 0.30650(9) 0.0185(3) Uani 1 1 d . . . . .
H5 H -0.586367 -0.123997 0.325423 0.022 Uiso 1 1 calc R U . . .
C6 C -0.6027(2) -0.03178(19) 0.23747(9) 0.0195(3) Uani 1 1 d . . . . .
H6 H -0.685120 -0.121314 0.208553 0.023 Uiso 1 1 calc R U . . .
C7 C -0.3293(2) -0.02354(18) 0.43902(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C -0.2473(2) 0.03517(18) 0.50646(9) 0.0165(3) Uani 1 1 d . . . . .
C9 C -0.1822(2) -0.03799(18) 0.55571(8) 0.0161(3) Uani 1 1 d . . . . .
C10 C -0.2024(2) -0.19103(18) 0.54742(8) 0.0172(3) Uani 1 1 d . . . . .
H10 H -0.263624 -0.269577 0.508295 0.021 Uiso 1 1 calc R U . . .
C11 C -0.1139(2) -0.20411(18) 0.60852(9) 0.0171(3) Uani 1 1 d . . . . .
C12 C -0.1619(3) -0.46387(18) 0.57539(9) 0.0236(4) Uani 1 1 d . . . . .
H12A H -0.293962 -0.495311 0.569194 0.035 Uiso 1 1 calc R U . . .
H12B H -0.129810 -0.543261 0.592194 0.035 Uiso 1 1 calc R U . . .
H12C H -0.111212 -0.447329 0.529635 0.035 Uiso 1 1 calc R U . . .
C13 C -0.0429(2) -0.05983(18) 0.65364(8) 0.0162(3) Uani 1 1 d . . . . .
C14 C 0.0502(2) -0.02767(18) 0.71997(8) 0.0166(3) Uani 1 1 d . . . . .
H14 H 0.070027 -0.110158 0.735603 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2121(2) 0.12577(18) 0.83336(8) 0.0172(3) Uani 1 1 d . . . . .
H15 H 0.254002 0.038923 0.833740 0.021 Uiso 1 1 calc R U . . .
C16 C 0.0900(2) 0.12951(19) 0.89403(9) 0.0205(3) Uani 1 1 d . . . . .
H16A H -0.014672 0.032666 0.887147 0.025 Uiso 1 1 calc R U . . .
H16B H 0.043183 0.212415 0.893361 0.025 Uiso 1 1 calc R U . . .
C17 C 0.1942(2) 0.1541(2) 0.96620(9) 0.0237(4) Uani 1 1 d . . . . .
H17A H 0.114752 0.161882 1.005016 0.028 Uiso 1 1 calc R U . . .
H17B H 0.230331 0.066084 0.968671 0.028 Uiso 1 1 calc R U . . .
C18 C 0.3628(2) 0.2986(2) 0.97672(9) 0.0234(4) Uani 1 1 d . . . . .
H18A H 0.326026 0.387799 0.979520 0.028 Uiso 1 1 calc R U . . .
H18B H 0.432129 0.308907 1.022261 0.028 Uiso 1 1 calc R U . . .
C19 C 0.4829(2) 0.2947(2) 0.91515(9) 0.0237(4) Uani 1 1 d . . . . .
H19A H 0.588160 0.391162 0.921949 0.028 Uiso 1 1 calc R U . . .
H19B H 0.529080 0.211263 0.915194 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3783(2) 0.27154(19) 0.84351(9) 0.0204(3) Uani 1 1 d . . . . .
H20A H 0.457396 0.265589 0.804371 0.024 Uiso 1 1 calc R U . . .
H20B H 0.340117 0.358830 0.841840 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1531(3) 0.6402(3) 0.93153(12) 0.0392(5) Uani 1 1 d . . . . .
H21A H 0.244640 0.634990 0.898344 0.059 Uiso 1 1 calc R U . . .
H21B H 0.157060 0.582383 0.969020 0.059 Uiso 1 1 calc R U . . .
H21C H 0.177722 0.746181 0.953195 0.059 Uiso 1 1 calc R U . . .
C22 C -0.0333(2) 0.5735(2) 0.89125(10) 0.0252(4) Uani 1 1 d . . . . .
H22A H -0.125683 0.573869 0.925497 0.030 Uiso 1 1 calc R U . . .
H22B H -0.056799 0.466783 0.869076 0.030 Uiso 1 1 calc R U . . .
C23 C -0.0524(2) 0.6607(2) 0.83329(10) 0.0233(4) Uani 1 1 d . . . . .
H23A H -0.030975 0.766806 0.855870 0.028 Uiso 1 1 calc R U . . .
H23B H 0.042599 0.662560 0.800016 0.028 Uiso 1 1 calc R U . . .
C24 C -0.2356(3) 0.5951(2) 0.79074(10) 0.0264(4) Uani 1 1 d . . . . .
H24A H -0.330509 0.595809 0.823719 0.032 Uiso 1 1 calc R U . . .
H24B H -0.238513 0.660937 0.756165 0.032 Uiso 1 1 calc R U . . .
N1 N -0.35435(18) 0.09492(15) 0.41648(7) 0.0169(3) Uani 1 1 d . . . . .
N2 N -0.2917(2) 0.22218(16) 0.46801(8) 0.0213(3) Uani 1 1 d . . . . .
N3 N -0.2271(2) 0.18530(16) 0.52280(8) 0.0209(3) Uani 1 1 d . . . . .
N4 N -0.08821(18) 0.03946(16) 0.61818(7) 0.0157(3) Uani 1 1 d . . . . .
N5 N 0.11432(19) 0.10308(16) 0.76382(7) 0.0181(3) Uani 1 1 d . . . . .
O1 O -0.08915(17) -0.32438(12) 0.62742(6) 0.0212(3) Uani 1 1 d . . . . .
O2 O -0.27654(18) 0.44399(15) 0.75286(7) 0.0281(3) Uani 1 1 d . . . . .
O1W O 0.4342(2) 0.35515(16) 0.64384(8) 0.0322(3) Uani 1 1 d . . . . .
Cl1 Cl -0.60222(6) 0.10344(5) 0.12348(2) 0.02535(11) Uani 1 1 d . . . . .
Cl2 Cl 0.07036(5) 0.37947(4) 0.70754(2) 0.02138(11) Uani 1 1 d . . . . .
H4N H -0.056(3) 0.130(3) 0.6331(11) 0.026 Uiso 1 1 d . U . . .
H5N H 0.099(3) 0.177(3) 0.7525(11) 0.026 Uiso 1 1 d . U . . .
H7 H -0.365(3) -0.119(3) 0.4110(11) 0.026 Uiso 1 1 d . U . . .
H1W H 0.340(3) 0.380(2) 0.6625(11) 0.026 Uiso 1 1 d . U . . .
H2W H 0.519(3) 0.385(2) 0.6785(12) 0.026 Uiso 1 1 d . U . . .
H1S H -0.185(3) 0.430(2) 0.7376(11) 0.026 Uiso 1 1 d . 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
C1 C6 1.388(2) . ?
C1 C2 1.389(2) . ?
C1 Cl1 1.7451(16) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 N1 1.428(2) . ?
C5 C6 1.390(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.353(2) . ?
C7 C8 1.365(2) . ?
C7 H7 0.92(2) . ?
C8 N3 1.372(2) . ?
C8 C9 1.447(2) . ?
C9 N4 1.345(2) . ?
C9 C10 1.400(2) . ?
C10 C11 1.394(2) . ?
C10 H10 0.9500 . ?
C11 O1 1.3385(19) . ?
C11 C13 1.418(2) . ?
C12 O1 1.450(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.383(2) . ?
C13 N4 1.391(2) . ?
C14 N5 1.311(2) . ?
C14 H14 0.9500 . ?
C15 N5 1.467(2) . ?
C15 C16 1.525(2) . ?
C15 C20 1.526(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.530(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.530(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.528(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.526(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.519(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.526(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.518(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O2 1.429(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N1 N2 1.364(2) . ?
N2 N3 1.306(2) . ?
N4 H4N 0.82(2) . ?
N5 H5N 0.82(2) . ?
O2 H1S 0.83(2) . ?
O1W H1W 0.92(2) . ?
O1W H2W 0.87(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
C6 C1 C2 122.02(15) . . ?
C6 C1 Cl1 119.01(13) . . ?
C2 C1 Cl1 118.96(13) . . ?
C3 C2 C1 119.14(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.10(16) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.65(15) . . ?
C5 C4 N1 119.04(14) . . ?
C3 C4 N1 119.25(15) . . ?
C4 C5 C6 119.32(15) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 118.75(16) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C7 C8 104.19(14) . . ?
N1 C7 H7 122.5(13) . . ?
C8 C7 H7 133.3(13) . . ?
C7 C8 N3 109.08(14) . . ?
C7 C8 C9 128.98(15) . . ?
N3 C8 C9 121.91(15) . . ?
N4 C9 C10 110.43(14) . . ?
N4 C9 C8 121.88(14) . . ?
C10 C9 C8 127.69(15) . . ?
C11 C10 C9 105.67(14) . . ?
C11 C10 H10 127.2 . . ?
C9 C10 H10 127.2 . . ?
O1 C11 C10 130.62(15) . . ?
O1 C11 C13 120.66(14) . . ?
C10 C11 C13 108.71(14) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N4 127.82(15) . . ?
C14 C13 C11 125.93(14) . . ?
N4 C13 C11 106.25(14) . . ?
N5 C14 C13 127.73(15) . . ?
N5 C14 H14 116.1 . . ?
C13 C14 H14 116.1 . . ?
N5 C15 C16 111.27(13) . . ?
N5 C15 C20 109.60(13) . . ?
C16 C15 C20 110.97(13) . . ?
N5 C15 H15 108.3 . . ?
C16 C15 H15 108.3 . . ?
C20 C15 H15 108.3 . . ?
C15 C16 C17 110.65(14) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 110.84(14) . . ?
C18 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 110.86(14) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C20 C19 C18 111.10(14) . . ?
C20 C19 H19A 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C19 C20 C15 110.01(13) . . ?
C19 C20 H20A 109.7 . . ?
C15 C20 H20A 109.7 . . ?
C19 C20 H20B 109.7 . . ?
C15 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C21 C22 C23 112.66(15) . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 114.15(15) . . ?
C24 C23 H23A 108.7 . . ?
C22 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
O2 C24 C23 113.43(15) . . ?
O2 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
O2 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C7 N1 N2 111.05(13) . . ?
C7 N1 C4 127.90(14) . . ?
N2 N1 C4 120.92(13) . . ?
N3 N2 N1 106.90(13) . . ?
N2 N3 C8 108.78(14) . . ?
C9 N4 C13 108.93(14) . . ?
C9 N4 H4N 127.4(15) . . ?
C13 N4 H4N 123.6(15) . . ?
C14 N5 C15 123.61(14) . . ?
C14 N5 H5N 119.2(15) . . ?
C15 N5 H5N 117.2(16) . . ?
C11 O1 C12 115.29(13) . . ?
C24 O2 H1S 112.1(16) . . ?
H1W O1W H2W 106.0(19) . . ?

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
C6 C1 C2 C3 1.5(3) . . . . ?
Cl1 C1 C2 C3 -176.81(13) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 N1 175.59(15) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
N1 C4 C5 C6 -175.58(14) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
Cl1 C1 C6 C5 176.83(12) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
N1 C7 C8 N3 0.60(18) . . . . ?
N1 C7 C8 C9 -177.44(16) . . . . ?
C7 C8 C9 N4 173.49(16) . . . . ?
N3 C8 C9 N4 -4.3(2) . . . . ?
C7 C8 C9 C10 -5.9(3) . . . . ?
N3 C8 C9 C10 176.29(16) . . . . ?
N4 C9 C10 C11 -0.40(18) . . . . ?
C8 C9 C10 C11 179.05(15) . . . . ?
C9 C10 C11 O1 -178.66(16) . . . . ?
C9 C10 C11 C13 0.70(18) . . . . ?
O1 C11 C13 C14 -2.2(3) . . . . ?
C10 C11 C13 C14 178.39(15) . . . . ?
O1 C11 C13 N4 178.69(14) . . . . ?
C10 C11 C13 N4 -0.74(18) . . . . ?
N4 C13 C14 N5 0.6(3) . . . . ?
C11 C13 C14 N5 -178.37(17) . . . . ?
N5 C15 C16 C17 -179.68(13) . . . . ?
C20 C15 C16 C17 -57.36(18) . . . . ?
C15 C16 C17 C18 56.05(19) . . . . ?
C16 C17 C18 C19 -55.6(2) . . . . ?
C17 C18 C19 C20 56.49(19) . . . . ?
C18 C19 C20 C15 -57.24(19) . . . . ?
N5 C15 C20 C19 -178.98(13) . . . . ?
C16 C15 C20 C19 57.73(18) . . . . ?
C21 C22 C23 C24 178.65(17) . . . . ?
C22 C23 C24 O2 -61.4(2) . . . . ?
C8 C7 N1 N2 -0.42(18) . . . . ?
C8 C7 N1 C4 175.34(15) . . . . ?
C5 C4 N1 C7 28.3(2) . . . . ?
C3 C4 N1 C7 -148.78(16) . . . . ?
C5 C4 N1 N2 -156.30(15) . . . . ?
C3 C4 N1 N2 26.6(2) . . . . ?
C7 N1 N2 N3 0.08(18) . . . . ?
C4 N1 N2 N3 -176.02(14) . . . . ?
N1 N2 N3 C8 0.30(18) . . . . ?
C7 C8 N3 N2 -0.58(19) . . . . ?
C9 C8 N3 N2 177.62(15) . . . . ?
C10 C9 N4 C13 -0.06(18) . . . . ?
C8 C9 N4 C13 -179.55(14) . . . . ?
C14 C13 N4 C9 -178.62(16) . . . . ?
C11 C13 N4 C9 0.49(17) . . . . ?
C13 C14 N5 C15 -179.84(15) . . . . ?
C16 C15 N5 C14 -101.11(18) . . . . ?
C20 C15 N5 C14 135.78(16) . . . . ?
C10 C11 O1 C12 1.7(2) . . . . ?
C13 C11 O1 C12 -177.56(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B N3 0.98 2.56 3.199(2) 123.2 1_545
C16 H16A Cl1 0.99 2.84 3.6954(17) 145.3 2_456
C20 H20A O2 0.99 2.53 3.335(2) 137.9 1_655
N4 H4N Cl2 0.82(2) 2.42(2) 3.2109(14) 163.3(19) .
N5 H5N Cl2 0.82(2) 2.33(2) 3.1413(14) 173(2) .
C7 H7 O1W 0.92(2) 2.20(2) 3.119(2) 172.1(18) 2_556
O1W H1W Cl2 0.92(2) 2.31(2) 3.2158(15) 165.9(18) .
O1W H2W O2 0.87(2) 1.99(2) 2.856(2) 176(2) 1_655
O2 H1S Cl2 0.83(2) 2.30(2) 3.1289(14) 173(2) .

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_MM75
_database_code_depnum_ccdc_archive 'CCDC 1979550'
loop_
_audit_author_name
_audit_author_address
'Israel Carreira-Barral'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        MM75
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl N5 O, Cl'
_chemical_formula_sum            'C17 H17 Cl2 N5 O'
_chemical_formula_weight         378.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   5.7035(14)
_cell_length_b                   20.182(5)
_cell_length_c                   15.891(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.478(4)
_cell_angle_gamma                90
_cell_volume                     1817.5(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5853
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.61

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.373
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20460
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         28.291
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4221
_reflns_number_gt                2758
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0855P)²] 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         4221
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5986(4) 0.11714(12) 0.36379(13) 0.0620(6) Uani 1 1 d . . . . .
C2 C 0.5272(4) 0.17774(11) 0.38997(14) 0.0612(5) Uani 1 1 d . . . . .
H2 H 0.591754 0.217180 0.369456 0.073 Uiso 1 1 calc R U . . .
C3 C 0.3611(4) 0.18102(10) 0.44632(13) 0.0550(5) Uani 1 1 d . . . . .
H3 H 0.310788 0.222789 0.465218 0.066 Uiso 1 1 calc R U . . .
C4 C 0.2683(3) 0.12352(9) 0.47507(12) 0.0469(4) Uani 1 1 d . . . . .
C5 C 0.3377(4) 0.06266(10) 0.44684(13) 0.0596(5) Uani 1 1 d . . . . .
H5 H 0.269642 0.023131 0.465608 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5063(4) 0.05957(12) 0.39129(14) 0.0675(6) Uani 1 1 d . . . . .
H6 H 0.557856 0.017952 0.372347 0.081 Uiso 1 1 calc R U . . .
C7 C -0.0440(3) 0.17602(9) 0.55147(12) 0.0481(4) Uani 1 1 d . . . . .
C8 C -0.1687(3) 0.15235(9) 0.61317(12) 0.0477(4) Uani 1 1 d . . . . .
C9 C -0.3528(3) 0.18450(9) 0.65357(11) 0.0477(4) Uani 1 1 d . . . . .
C10 C -0.4914(3) 0.16119(9) 0.71361(12) 0.0534(5) Uani 1 1 d . . . . .
H10 H -0.480279 0.119061 0.740415 0.064 Uiso 1 1 calc R U . . .
C11 C -0.6492(3) 0.21126(10) 0.72685(13) 0.0533(5) Uani 1 1 d . . . . .
C12 C -0.8434(5) 0.15720(13) 0.82979(16) 0.0802(7) Uani 1 1 d . . . . .
H12A H -0.874370 0.117936 0.793963 0.120 Uiso 1 1 calc R U . . .
H12B H -0.974735 0.164013 0.863632 0.120 Uiso 1 1 calc R U . . .
H12C H -0.697094 0.150726 0.867558 0.120 Uiso 1 1 calc R U . . .
C13 C -0.6038(3) 0.26538(9) 0.67467(12) 0.0498(5) Uani 1 1 d . . . . .
C14 C -0.7135(4) 0.32648(10) 0.66664(14) 0.0576(5) Uani 1 1 d . . . . .
H14 H -0.840100 0.334321 0.699429 0.069 Uiso 1 1 calc R U . . .
C15 C -0.7772(5) 0.43755(12) 0.60654(19) 0.0893(8) Uani 1 1 d . . . . .
H15 H -0.916791 0.437610 0.562411 0.107 Uiso 1 1 calc R U . . .
C16 C -0.6491(6) 0.49579(15) 0.6116(3) 0.1354(15) Uani 1 1 d . . . . .
H16A H -0.701447 0.531728 0.571382 0.162 Uiso 1 1 calc R U . . .
H16B H -0.476283 0.492766 0.626816 0.162 Uiso 1 1 calc R U . . .
C17 C -0.8001(8) 0.47895(16) 0.6760(3) 0.1374(15) Uani 1 1 d . . . . .
H17A H -0.723954 0.464883 0.732194 0.165 Uiso 1 1 calc R U . . .
H17B H -0.949320 0.503880 0.676709 0.165 Uiso 1 1 calc R U . . .
N1 N 0.0988(3) 0.12606(7) 0.53445(10) 0.0472(4) Uani 1 1 d . . . . .
N2 N 0.0655(3) 0.07312(8) 0.58432(11) 0.0601(5) Uani 1 1 d . . . . .
N3 N -0.0978(3) 0.08908(8) 0.63196(11) 0.0593(5) Uani 1 1 d . . . . .
N4 N -0.4187(3) 0.24639(7) 0.63144(10) 0.0487(4) Uani 1 1 d . . . . .
N5 N -0.6563(3) 0.37429(8) 0.61733(13) 0.0640(5) Uani 1 1 d . . . . .
O1 O -0.8200(3) 0.21393(8) 0.77760(10) 0.0678(4) Uani 1 1 d . . . . .
Cl1 Cl 0.81069(11) 0.11232(4) 0.29371(5) 0.0971(3) Uani 1 1 d . . . . .
Cl2 Cl 0.74044(10) 0.33953(3) 0.49728(4) 0.0709(2) Uani 1 1 d . . . . .
H7 H -0.045(3) 0.2146(10) 0.5216(13) 0.056(6) Uiso 1 1 d . . . . .
H4N H -0.358(3) 0.2688(10) 0.5944(13) 0.058(6) Uiso 1 1 d . . . . .
H5N H -0.536(5) 0.3676(13) 0.5750(17) 0.094(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.367(3) . ?
C1 C2 1.368(3) . ?
C1 Cl1 1.737(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 N1 1.426(2) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.343(2) . ?
C7 C8 1.361(3) . ?
C7 H7 0.91(2) . ?
C8 N3 1.362(2) . ?
C8 C9 1.445(3) . ?
C9 N4 1.340(2) . ?
C9 C10 1.388(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 O1 1.334(2) . ?
C11 C13 1.413(3) . ?
C12 O1 1.429(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N4 1.377(2) . ?
C13 C14 1.382(3) . ?
C14 N5 1.307(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 C17 1.401(4) . ?
C15 N5 1.452(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.450(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N1 N2 1.356(2) . ?
N2 N3 1.305(2) . ?
N4 H4N 0.85(2) . ?
N5 H5N 1.02(3) . ?

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
C6 C1 C2 121.6(2) . . ?
C6 C1 Cl1 118.57(18) . . ?
C2 C1 Cl1 119.84(18) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.63(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.51(19) . . ?
C3 C4 N1 120.30(16) . . ?
C5 C4 N1 119.19(16) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 C8 105.05(17) . . ?
N1 C7 H7 120.3(12) . . ?
C8 C7 H7 134.5(12) . . ?
C7 C8 N3 108.68(16) . . ?
C7 C8 C9 128.86(17) . . ?
N3 C8 C9 122.44(17) . . ?
N4 C9 C10 109.35(17) . . ?
N4 C9 C8 119.91(17) . . ?
C10 C9 C8 130.70(18) . . ?
C11 C10 C9 106.71(17) . . ?
C11 C10 H10 126.6 . . ?
C9 C10 H10 126.6 . . ?
O1 C11 C10 130.73(19) . . ?
O1 C11 C13 121.22(18) . . ?
C10 C11 C13 108.05(17) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 124.53(18) . . ?
N4 C13 C11 106.20(16) . . ?
C14 C13 C11 129.26(19) . . ?
N5 C14 C13 124.94(19) . . ?
N5 C14 H14 117.5 . . ?
C13 C14 H14 117.5 . . ?
C16 C15 C17 62.8(2) . . ?
C16 C15 N5 120.0(3) . . ?
C17 C15 N5 121.1(3) . . ?
C16 C15 H15 114.4 . . ?
C17 C15 H15 114.4 . . ?
N5 C15 H15 114.4 . . ?
C15 C16 C17 59.3(2) . . ?
C15 C16 H16A 117.8 . . ?
C17 C16 H16A 117.8 . . ?
C15 C16 H16B 117.8 . . ?
C17 C16 H16B 117.8 . . ?
H16A C16 H16B 115.0 . . ?
C15 C17 C16 57.9(2) . . ?
C15 C17 H17A 118.0 . . ?
C16 C17 H17A 118.0 . . ?
C15 C17 H17B 118.0 . . ?
C16 C17 H17B 118.0 . . ?
H17A C17 H17B 115.1 . . ?
C7 N1 N2 110.22(16) . . ?
C7 N1 C4 129.21(15) . . ?
N2 N1 C4 120.56(14) . . ?
N3 N2 N1 107.50(15) . . ?
N2 N3 C8 108.54(16) . . ?
C9 N4 C13 109.69(16) . . ?
C9 N4 H4N 123.7(14) . . ?
C13 N4 H4N 126.5(14) . . ?
C14 N5 C15 124.9(2) . . ?
C14 N5 H5N 121.9(15) . . ?
C15 N5 H5N 112.5(15) . . ?
C11 O1 C12 116.17(17) . . ?

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
C6 C1 C2 C3 1.0(3) . . . . ?
Cl1 C1 C2 C3 -179.23(15) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 N1 179.02(17) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
N1 C4 C5 C6 -178.17(18) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
Cl1 C1 C6 C5 -179.93(16) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
N1 C7 C8 N3 0.2(2) . . . . ?
N1 C7 C8 C9 -178.00(17) . . . . ?
C7 C8 C9 N4 -0.7(3) . . . . ?
N3 C8 C9 N4 -178.71(17) . . . . ?
C7 C8 C9 C10 176.6(2) . . . . ?
N3 C8 C9 C10 -1.4(3) . . . . ?
N4 C9 C10 C11 0.9(2) . . . . ?
C8 C9 C10 C11 -176.67(18) . . . . ?
C9 C10 C11 O1 179.62(18) . . . . ?
C9 C10 C11 C13 -0.4(2) . . . . ?
O1 C11 C13 N4 179.80(16) . . . . ?
C10 C11 C13 N4 -0.2(2) . . . . ?
O1 C11 C13 C14 0.7(3) . . . . ?
C10 C11 C13 C14 -179.26(19) . . . . ?
N4 C13 C14 N5 -0.2(3) . . . . ?
C11 C13 C14 N5 178.8(2) . . . . ?
N5 C15 C16 C17 -111.9(3) . . . . ?
N5 C15 C17 C16 110.3(3) . . . . ?
C8 C7 N1 N2 -0.4(2) . . . . ?
C8 C7 N1 C4 -179.84(17) . . . . ?
C3 C4 N1 C7 21.8(3) . . . . ?
C5 C4 N1 C7 -158.14(19) . . . . ?
C3 C4 N1 N2 -157.56(17) . . . . ?
C5 C4 N1 N2 22.5(3) . . . . ?
C7 N1 N2 N3 0.5(2) . . . . ?
C4 N1 N2 N3 179.95(16) . . . . ?
N1 N2 N3 C8 -0.3(2) . . . . ?
C7 C8 N3 N2 0.1(2) . . . . ?
C9 C8 N3 N2 178.42(17) . . . . ?
C10 C9 N4 C13 -1.0(2) . . . . ?
C8 C9 N4 C13 176.85(16) . . . . ?
C14 C13 N4 C9 179.85(17) . . . . ?
C11 C13 N4 C9 0.7(2) . . . . ?
C13 C14 N5 C15 177.6(2) . . . . ?
C16 C15 N5 C14 131.8(3) . . . . ?
C17 C15 N5 C14 57.3(4) . . . . ?
C10 C11 O1 C12 2.3(3) . . . . ?
C13 C11 O1 C12 -177.68(19) . . . . ?

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
C12 H12B Cl2 0.98 2.82 3.761(3) 162.2 4_366
C14 H14 Cl1 0.95 2.84 3.769(2) 167.2 4_366
C15 H15 Cl2 1.00 2.89 3.663(3) 134.7 1_355
C16 H16A Cl2 0.99 2.82 3.756(3) 158.5 3_566
C7 H7 Cl2 0.91(2) 2.81(2) 3.592(2) 144.6(15) 1_455
N4 H4N Cl2 0.85(2) 2.22(2) 3.0561(18) 169.0(18) 1_455
N5 H5N Cl2 1.02(3) 2.19(3) 3.198(2) 171(2) 1_455

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069

