# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02199CristobaldelosRios
_database_code_depnum_ccdc_archive 'CCDC 2013556'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            EG607_200K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 N4 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         376.45
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.5359(14)
_cell_length_b                   5.1353(6)
_cell_length_c                   13.931(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.691(5)
_cell_angle_gamma                90
_cell_volume                     940.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    885
_cell_measurement_theta_min      3.0425
_cell_measurement_theta_max      19.0917
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'dark blue brown'
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400

_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11012
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.1371
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3428
_reflns_number_gt                2026
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1640
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         3428
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 583 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9043(4) 0.8971(13) 0.7445(5) 0.0231(16) Uani d . . . 1 . .
C C2 0.8477(4) 0.5761(14) 0.6328(5) 0.0207(15) Uani d . . . 1 . .
C C3 0.9396(4) 0.6980(12) 0.6086(5) 0.0202(16) Uani d . . . 1 . .
C C4 0.9694(4) 0.9089(13) 0.6805(5) 0.0213(16) Uani d . . . 1 . .
C C5 1.0457(4) 1.0945(15) 0.6963(5) 0.0274(16) Uani d . . . 1 . .
H H5 1.0913 1.1085 0.6542 0.033 Uiso calc U . R 1 . .
C C6 1.0525(5) 1.2569(15) 0.7756(5) 0.0292(17) Uani d . . . 1 . .
H H6 1.1029 1.3894 0.7889 0.035 Uiso calc U . R 1 . .
C C7 0.9857(5) 1.2274(14) 0.8362(5) 0.0327(19) Uani d . . . 1 . .
H H7 0.9937 1.3405 0.8914 0.039 Uiso calc U . R 1 . .
C C8 0.7599(4) 0.0817(15) 0.4543(5) 0.0242(16) Uani d . . . 1 . .
C C9 0.7945(4) 0.3825(13) 0.5773(5) 0.0235(16) Uani d . . . 1 . .
C C10 0.6927(4) 0.2613(14) 0.5762(5) 0.0246(16) Uani d . . . 1 . .
C C11 0.6757(4) 0.0736(14) 0.4966(5) 0.0221(15) Uani d . . . 1 . .
C C12 0.5986(5) -0.0991(14) 0.4600(5) 0.0319(18) Uani d . . . 1 . .
H H12 0.5409 -0.1114 0.4874 0.038 Uiso calc U . R 1 . .
C C13 0.6083(5) -0.2553(16) 0.3813(5) 0.0375(19) Uani d . . . 1 . .
H H13 0.5565 -0.3763 0.3529 0.045 Uiso calc U . R 1 . .
C C14 0.6940(5) -0.2319(17) 0.3451(5) 0.0371(19) Uani d . . . 1 . .
H H14 0.6989 -0.3426 0.2917 0.045 Uiso calc U . R 1 . .
C C15 0.7676(4) 0.6191(15) 0.7844(5) 0.0264(17) Uani d . . . 1 . .
H H15A 0.8074 0.6444 0.8532 0.032 Uiso calc U . R 1 . .
H H15B 0.7541 0.4303 0.7746 0.032 Uiso calc U . R 1 . .
C C16 0.6664(4) 0.7608(15) 0.7714(5) 0.0300(17) Uani d . . . 1 . .
H H16A 0.6787 0.9447 0.792 0.036 Uiso calc U . R 1 . .
H H16B 0.6298 0.7583 0.7009 0.036 Uiso calc U . R 1 . .
C C17 0.6015(4) 0.6304(15) 0.8332(5) 0.0272(17) Uani d . . . 1 . .
H H17A 0.5912 0.4458 0.8127 0.033 Uiso calc U . R 1 . .
H H17B 0.6393 0.6332 0.9033 0.033 Uiso calc U . R 1 . .
C C18 0.4984(4) 0.7552(15) 0.8250(5) 0.0295(17) Uani d . . . 1 . .
H H18A 0.459 0.7453 0.7555 0.035 Uiso calc U . R 1 . .
H H18B 0.5081 0.9415 0.843 0.035 Uiso calc U . R 1 . .
C C19 0.4377(4) 0.6257(16) 0.8911(5) 0.0318(18) Uani d . . . 1 . .
H H19A 0.427 0.4404 0.8718 0.038 Uiso calc U . R 1 . .
H H19B 0.4784 0.631 0.9602 0.038 Uiso calc U . R 1 . .
C C20 0.3352(4) 0.7498(15) 0.8869(5) 0.0308(17) Uani d . . . 1 . .
H H20A 0.3453 0.9369 0.9036 0.037 Uiso calc U . R 1 . .
H H20B 0.2929 0.7372 0.8186 0.037 Uiso calc U . R 1 . .
C C21 0.2793(4) 0.6234(16) 0.9569(5) 0.0334(19) Uani d . . . 1 . .
H H21A 0.3238 0.6242 1.0244 0.04 Uiso calc U . R 1 . .
H H21B 0.2648 0.4396 0.937 0.04 Uiso calc U . R 1 . .
C C22 0.1791(5) 0.7605(16) 0.9586(5) 0.0375(19) Uani d . . . 1 . .
H H22A 0.1926 0.9436 0.9769 0.056 Uiso calc U . R 1 . .
H H22B 0.1478 0.6753 1.0071 0.056 Uiso calc U . R 1 . .
H H22C 0.1327 0.7502 0.893 0.056 Uiso calc U . R 1 . .
H H3N 0.890(5) 0.279(15) 0.490(5) 0.04(2) Uiso d . . . 1 . .
N N1 0.8302(3) 0.7056(10) 0.7162(4) 0.0240(15) Uani d . . . 1 . .
N N2 0.9093(4) 1.0491(11) 0.8228(4) 0.0284(15) Uani d . . . 1 . .
N N3 0.8276(4) 0.2673(12) 0.5000(4) 0.0243(14) Uani d . . . 1 . .
N N4 0.7721(4) -0.0651(12) 0.3787(4) 0.0317(15) Uani d . . . 1 . .
O O1 0.9779(3) 0.6304(9) 0.5419(3) 0.0266(12) Uani d . . . 1 . .
O O2 0.6343(3) 0.3218(10) 0.6280(4) 0.0358(14) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.330(8) ?
C1 N1 . 1.394(8) ?
C1 C4 . 1.394(9) ?
C2 C9 . 1.358(9) ?
C2 N1 . 1.406(8) ?
C2 C3 . 1.499(8) ?
C3 O1 . 1.217(7) ?
C3 C4 . 1.465(9) ?
C4 C5 . 1.385(9) ?
C5 C6 . 1.369(9) ?
C6 C7 . 1.385(9) ?
C7 N2 . 1.360(8) ?
C8 N4 . 1.337(8) ?
C8 N3 . 1.371(9) ?
C8 C11 . 1.402(8) ?
C9 N3 . 1.393(8) ?
C9 C10 . 1.508(8) ?
C10 O2 . 1.230(7) ?
C10 C11 . 1.446(9) ?
C11 C12 . 1.372(9) ?
C12 C13 . 1.389(9) ?
C13 C14 . 1.375(9) ?
C14 N4 . 1.355(9) ?
C15 N1 . 1.482(7) ?
C15 C16 . 1.524(9) ?
C16 C17 . 1.522(8) ?
C17 C18 . 1.515(8) ?
C18 C19 . 1.525(8) ?
C19 C20 . 1.515(8) ?
C20 C21 . 1.515(8) ?
C21 C22 . 1.533(9) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 N1 . . 122.7(6) ?
N2 C1 C4 . . 125.5(6) ?
N1 C1 C4 . . 111.8(6) ?
C9 C2 N1 . . 130.2(5) ?
C9 C2 C3 . . 122.3(6) ?
N1 C2 C3 . . 107.4(6) ?
O1 C3 C4 . . 129.4(6) ?
O1 C3 C2 . . 125.3(6) ?
C4 C3 C2 . . 105.3(5) ?
C5 C4 C1 . . 119.3(6) ?
C5 C4 C3 . . 133.8(6) ?
C1 C4 C3 . . 106.9(5) ?
C6 C5 C4 . . 116.9(6) ?
C5 C6 C7 . . 119.7(7) ?
N2 C7 C6 . . 125.1(7) ?
N4 C8 N3 . . 124.4(5) ?
N4 C8 C11 . . 125.4(6) ?
N3 C8 C11 . . 110.3(6) ?
C2 C9 N3 . . 121.8(5) ?
C2 C9 C10 . . 132.0(6) ?
N3 C9 C10 . . 106.1(6) ?
O2 C10 C11 . . 127.6(6) ?
O2 C10 C9 . . 127.0(7) ?
C11 C10 C9 . . 105.2(5) ?
C12 C11 C8 . . 119.0(6) ?
C12 C11 C10 . . 133.3(6) ?
C8 C11 C10 . . 107.7(5) ?
C11 C12 C13 . . 117.5(6) ?
C14 C13 C12 . . 119.0(7) ?
N4 C14 C13 . . 125.8(7) ?
N1 C15 C16 . . 114.5(5) ?
C17 C16 C15 . . 110.2(6) ?
C18 C17 C16 . . 114.6(6) ?
C17 C18 C19 . . 112.9(6) ?
C20 C19 C18 . . 114.3(6) ?
C21 C20 C19 . . 112.8(6) ?
C20 C21 C22 . . 113.1(6) ?
C1 N1 C2 . . 108.4(5) ?
C1 N1 C15 . . 120.8(5) ?
C2 N1 C15 . . 128.4(5) ?
C1 N2 C7 . . 113.4(5) ?
C8 N3 C9 . . 110.6(5) ?
C8 N4 C14 . . 113.4(6) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 C2 C3 O1 . . . . -3.7(10) ?
N1 C2 C3 O1 . . . . 178.3(6) ?
C9 C2 C3 C4 . . . . 175.7(6) ?
N1 C2 C3 C4 . . . . -2.3(6) ?
N2 C1 C4 C5 . . . . -1.1(10) ?
N1 C1 C4 C5 . . . . 178.1(6) ?
N2 C1 C4 C3 . . . . 177.0(6) ?
N1 C1 C4 C3 . . . . -3.8(7) ?
O1 C3 C4 C5 . . . . 0.7(12) ?
C2 C3 C4 C5 . . . . -178.7(7) ?
O1 C3 C4 C1 . . . . -177.0(6) ?
C2 C3 C4 C1 . . . . 3.6(7) ?
C1 C4 C5 C6 . . . . 0.2(10) ?
C3 C4 C5 C6 . . . . -177.3(7) ?
C4 C5 C6 C7 . . . . 1.0(10) ?
C5 C6 C7 N2 . . . . -1.6(11) ?
N1 C2 C9 N3 . . . . -176.1(7) ?
C3 C2 C9 N3 . . . . 6.4(9) ?
N1 C2 C9 C10 . . . . 8.8(12) ?
C3 C2 C9 C10 . . . . -168.6(7) ?
C2 C9 C10 O2 . . . . 1.2(12) ?
N3 C9 C10 O2 . . . . -174.5(6) ?
C2 C9 C10 C11 . . . . 177.1(7) ?
N3 C9 C10 C11 . . . . 1.4(7) ?
N4 C8 C11 C12 . . . . 0.8(10) ?
N3 C8 C11 C12 . . . . 179.3(6) ?
N4 C8 C11 C10 . . . . 179.8(6) ?
N3 C8 C11 C10 . . . . -1.7(8) ?
O2 C10 C11 C12 . . . . -5.2(13) ?
C9 C10 C11 C12 . . . . 178.9(7) ?
O2 C10 C11 C8 . . . . 176.0(6) ?
C9 C10 C11 C8 . . . . 0.1(7) ?
C8 C11 C12 C13 . . . . -0.8(10) ?
C10 C11 C12 C13 . . . . -179.4(7) ?
C11 C12 C13 C14 . . . . 0.7(11) ?
C12 C13 C14 N4 . . . . -0.7(12) ?
N1 C15 C16 C17 . . . . 171.3(5) ?
C15 C16 C17 C18 . . . . -179.5(6) ?
C16 C17 C18 C19 . . . . -177.6(6) ?
C17 C18 C19 C20 . . . . 178.5(6) ?
C18 C19 C20 C21 . . . . -177.5(6) ?
C19 C20 C21 C22 . . . . 175.8(6) ?
N2 C1 N1 C2 . . . . -178.4(6) ?
C4 C1 N1 C2 . . . . 2.4(7) ?
N2 C1 N1 C15 . . . . -14.4(9) ?
C4 C1 N1 C15 . . . . 166.4(5) ?
C9 C2 N1 C1 . . . . -177.7(6) ?
C3 C2 N1 C1 . . . . 0.0(7) ?
C9 C2 N1 C15 . . . . 19.9(10) ?
C3 C2 N1 C15 . . . . -162.4(5) ?
C16 C15 N1 C1 . . . . 93.8(7) ?
C16 C15 N1 C2 . . . . -105.7(7) ?
N1 C1 N2 C7 . . . . -178.5(6) ?
C4 C1 N2 C7 . . . . 0.6(9) ?
C6 C7 N2 C1 . . . . 0.7(10) ?
N4 C8 N3 C9 . . . . -178.7(6) ?
C11 C8 N3 C9 . . . . 2.7(8) ?
C2 C9 N3 C8 . . . . -178.7(6) ?
C10 C9 N3 C8 . . . . -2.5(7) ?
N3 C8 N4 C14 . . . . -179.0(7) ?
C11 C8 N4 C14 . . . . -0.7(10) ?
C13 C14 N4 C8 . . . . 0.6(11) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15B O2 . 0.99 2.35 2.911(8) 114.7 ?
C16 H16B O2 . 0.99 2.47 2.975(9) 111.4 ?
N3 H3N O1 . 0.89(6) 2.19(7) 2.719(7) 118.(6) ?
N3 H3N O1 2_746 0.89(6) 2.09(6) 2.915(6) 154.(7) ?

