# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_03341
_database_code_depnum_ccdc_archive 'CCDC 2095914'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            LM_Chlorine_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Cl N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         317.81
_chemical_absolute_configuration ad

_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                   7.262(6)
_cell_length_b                   10.514(6)
_cell_length_c                   11.343(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.63(3)
_cell_angle_gamma                90
_cell_volume                     858.4(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1035
_cell_measurement_theta_min      2.8539
_cell_measurement_theta_max      18.2618
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.093
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336

_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   'sealed tube'
_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       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7195
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_theta_full        25.31
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2999
_reflns_number_gt                1433
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1939
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.011
_refine_ls_number_reflns         2999
_refine_ls_number_parameters     199
_refine_ls_number_restraints     24
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0902P)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         0.362
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 465 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 0.8451(13) 0.3905(7) 0.7898(8) 0.061(2) Uani d . . . 1.0 . .
H H1 0.82274 0.305226 0.767375 0.073 Uiso calc U . R 1.0 . .
C C2 0.9802(12) 0.4159(9) 0.8791(8) 0.065(2) Uani d . . . 1.0 . .
H H2 1.052723 0.349865 0.916877 0.078 Uiso calc U . R 1.0 . .
C C3 1.0117(10) 0.5416(9) 0.9154(7) 0.059(2) Uani d . . . 1.0 . .
C C4 0.9079(12) 0.6358(7) 0.8580(8) 0.058(2) Uani d . . . 1.0 . .
H H4 0.930527 0.720909 0.880709 0.069 Uiso calc U . R 1.0 . .
C C5 0.7695(12) 0.6070(8) 0.7668(8) 0.059(2) Uani d . . . 1.0 . .
H H5 0.695341 0.672357 0.729132 0.071 Uiso calc U . R 1.0 . .
C C6 0.7394(12) 0.4821(8) 0.7304(8) 0.055(2) Uani d . . . 1.0 . .
C C7 0.4587(12) 0.5328(10) 0.5806(9) 0.0730(19) Uani d U . D 1.0 . .
H H7A 0.494022 0.623785 0.585435 0.088 Uiso calc U P R 0.443(13) A 1
H H7B 0.53(2) 0.582(16) 0.593(15) 0.088 Uiso d U P . 0.557(13) A 2
C C8A 0.287(3) 0.506(2) 0.649(2) 0.0730(19) Uani d . P D 0.443(13) A 1
H H8A1 0.297854 0.547315 0.727068 0.088 Uiso calc U P R 0.443(13) A 1
H H8A2 0.262622 0.414549 0.657461 0.088 Uiso calc U P R 0.443(13) A 1
C C9A 0.139(2) 0.573(2) 0.5530(15) 0.0730(19) Uani d . P D 0.443(13) A 1
H H9A1 0.012139 0.550189 0.566562 0.088 Uiso calc U P R 0.443(13) A 1
H H9A2 0.151769 0.665492 0.55847 0.088 Uiso calc U P R 0.443(13) A 1
C C10A 0.176(3) 0.526(3) 0.429(2) 0.0730(19) Uani d . P D 0.443(13) A 1
H H10A 0.147121 0.591179 0.366376 0.088 Uiso calc U P R 0.443(13) A 1
C C8B 0.289(2) 0.5586(17) 0.6459(16) 0.0730(19) Uani d . P D 0.557(13) A 2
H H8B1 0.31162 0.530042 0.728819 0.088 Uiso calc U P R 0.557(13) A 2
H H8B2 0.256793 0.649183 0.644078 0.088 Uiso calc U P R 0.557(13) A 2
C C9B 0.138(2) 0.4811(19) 0.5756(13) 0.0730(19) Uani d . P D 0.557(13) A 2
H H9B1 0.013807 0.506633 0.59157 0.088 Uiso calc U P R 0.557(13) A 2
H H9B2 0.155056 0.389682 0.589846 0.088 Uiso calc U P R 0.557(13) A 2
C C10B 0.175(2) 0.520(3) 0.4501(15) 0.0730(19) Uani d . P D 0.557(13) A 2
H H10B 0.156222 0.612717 0.443436 0.088 Uiso calc U P R 0.557(13) A 2
C C11 0.3837(9) 0.4953(8) 0.4548(6) 0.0491(19) Uani d U . D 1.0 . .
H H11A 0.398794 0.402192 0.447262 0.059 Uiso calc U P R 0.443(13) A 1
H H11B 0.439(15) 0.361(11) 0.374(11) 0.059 Uiso d U P . 0.557(13) A 2
C C12 0.4804(10) 0.5585(8) 0.3616(8) 0.061(2) Uani d . . . 1.0 . .
C C13 0.5388(10) 0.4860(8) 0.2647(7) 0.052(2) Uani d . . . 1.0 . .
C C14 0.5865(14) 0.3317(11) 0.1514(10) 0.083(3) Uani d . . . 1.0 . .
H H14 0.586825 0.249839 0.118247 0.1 Uiso calc U . R 1.0 . .
C C15 0.6510(12) 0.4333(11) 0.1031(9) 0.081(3) Uani d . . . 1.0 . .
H H15 0.707607 0.436027 0.033277 0.097 Uiso calc U . R 1.0 . .
C C16A 0.061(4) 0.404(3) 0.405(3) 0.112(10) Uiso d . P D 0.443(13) A 1
H H16A 0.050602 0.360718 0.479188 0.168 Uiso calc U P R 0.443(13) A 1
H H16B 0.121394 0.348086 0.353501 0.168 Uiso calc U P R 0.443(13) A 1
H H16C -0.062516 0.425175 0.365751 0.168 Uiso calc U P R 0.443(13) A 1
C C16B 0.057(3) 0.459(2) 0.3428(18) 0.096(7) Uiso d . P D 0.557(13) A 2
H H16D 0.09732 0.372377 0.333563 0.144 Uiso calc U P R 0.557(13) A 2
H H16E 0.072744 0.507488 0.271705 0.144 Uiso calc U P R 0.557(13) A 2
H H16F -0.072315 0.460289 0.354848 0.144 Uiso calc U P R 0.557(13) A 2
C C17 0.6684(16) 0.6659(10) 0.1491(9) 0.101(4) Uani d U . . 1.0 . .
H H17A 0.564146 0.720473 0.159682 0.152 Uiso calc U . R 1.0 . .
H H17B 0.696218 0.67348 0.068044 0.152 Uiso calc U . R 1.0 . .
H H17C 0.776071 0.691291 0.203908 0.152 Uiso calc U . R 1.0 . .
Cl Cl1 1.1850(3) 0.5757(3) 1.0325(3) 0.1041(11) Uani d . . . 1.0 . .
N N1 0.6103(11) 0.4524(6) 0.6330(7) 0.078(2) Uani d . . . 1.0 . .
H H1N 0.621187 0.378491 0.600095 0.094 Uiso calc U . R 1.0 . .
N N2 0.5180(10) 0.3593(6) 0.2569(7) 0.069(2) Uani d . . . 1.0 . .
N N3 0.6206(8) 0.5324(6) 0.1727(6) 0.0593(19) Uani d . . . 1.0 . .
O O1 0.5106(10) 0.6768(5) 0.3662(6) 0.089(2) Uani d . . . 1.0 . .


_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 C2 . 1.341(11) ?
C1 C6 . 1.354(11) ?
C2 C3 . 1.393(12) ?
C3 C4 . 1.357(11) ?
C3 Cl1 . 1.742(9) ?
C4 C5 . 1.377(11) ?
C5 C6 . 1.386(11) ?
C6 N1 . 1.387(11) ?
C7 N1 . 1.451(12) ?
C7 C11 . 1.510(12) ?
C7 C8B . 1.546(16) ?
C7 C8A . 1.582(19) ?
C8A C9A . 1.59(2) ?
C9A C10A . 1.54(2) ?
C10A C11 . 1.53(2) ?
C10A C16A . 1.54(2) ?
C8B C9B . 1.505(19) ?
C9B C10B . 1.538(19) ?
C10B C16B . 1.53(2) ?
C10B C11 . 1.532(19) ?
C11 C12 . 1.500(11) ?
C12 O1 . 1.263(9) ?
C12 C13 . 1.447(11) ?
C13 N2 . 1.342(10) ?
C13 N3 . 1.358(9) ?
C14 C15 . 1.314(12) ?
C14 N2 . 1.386(11) ?
C15 N3 . 1.343(11) ?
C17 N3 . 1.479(11) ?

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
C2 C1 C6 . . 122.9(8) ?
C1 C2 C3 . . 119.2(8) ?
C4 C3 C2 . . 119.4(8) ?
C4 C3 Cl1 . . 120.9(7) ?
C2 C3 Cl1 . . 119.6(7) ?
C3 C4 C5 . . 120.2(8) ?
C4 C5 C6 . . 120.2(8) ?
C1 C6 C5 . . 118.0(8) ?
C1 C6 N1 . . 121.0(8) ?
C5 C6 N1 . . 121.0(8) ?
N1 C7 C11 . . 113.1(8) ?
N1 C7 C8B . . 121.1(11) ?
C11 C7 C8B . . 106.8(9) ?
N1 C7 C8A . . 107.4(10) ?
C11 C7 C8A . . 102.0(11) ?
C7 C8A C9A . . 95.1(13) ?
C10A C9A C8A . . 107.3(18) ?
C11 C10A C16A . . 111.(2) ?
C11 C10A C9A . . 100.5(15) ?
C16A C10A C9A . . 106.(2) ?
C9B C8B C7 . . 102.8(11) ?
C8B C9B C10B . . 98.3(13) ?
C16B C10B C11 . . 113.8(15) ?
C16B C10B C9B . . 118.8(18) ?
C11 C10B C9B . . 102.6(13) ?
C12 C11 C7 . . 114.0(7) ?
C12 C11 C10B . . 117.1(10) ?
C7 C11 C10B . . 102.7(8) ?
C12 C11 C10A . . 108.3(12) ?
C7 C11 C10A . . 110.2(10) ?
O1 C12 C13 . . 119.0(8) ?
O1 C12 C11 . . 120.1(8) ?
C13 C12 C11 . . 120.9(7) ?
N2 C13 N3 . . 111.3(7) ?
N2 C13 C12 . . 122.1(7) ?
N3 C13 C12 . . 126.6(7) ?
C15 C14 N2 . . 112.3(9) ?
C14 C15 N3 . . 106.8(8) ?
C6 N1 C7 . . 126.2(7) ?
C13 N2 C14 . . 102.4(7) ?
C15 N3 C13 . . 107.2(7) ?
C15 N3 C17 . . 124.7(8) ?
C13 N3 C17 . . 128.1(7) ?

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
C6 C1 C2 C3 . . . . 1.6(12) ?
C1 C2 C3 C4 . . . . -1.4(11) ?
C1 C2 C3 Cl1 . . . . 179.3(6) ?
C2 C3 C4 C5 . . . . 1.6(11) ?
Cl1 C3 C4 C5 . . . . -179.0(6) ?
C3 C4 C5 C6 . . . . -2.1(11) ?
C2 C1 C6 C5 . . . . -2.1(12) ?
C2 C1 C6 N1 . . . . 175.3(7) ?
C4 C5 C6 C1 . . . . 2.3(11) ?
C4 C5 C6 N1 . . . . -175.1(7) ?
N1 C7 C8A C9A . . . . -165.3(13) ?
C11 C7 C8A C9A . . . . -46.1(16) ?
C7 C8A C9A C10A . . . . 46.(2) ?
C8A C9A C10A C11 . . . . -27.(3) ?
C8A C9A C10A C16A . . . . 88.(2) ?
N1 C7 C8B C9B . . . . -107.1(15) ?
C11 C7 C8B C9B . . . . 24.3(17) ?
C7 C8B C9B C10B . . . . -45.3(18) ?
C8B C9B C10B C16B . . . . 178.(2) ?
C8B C9B C10B C11 . . . . 51.1(19) ?
N1 C7 C11 C12 . . . . -89.1(9) ?
C8B C7 C11 C12 . . . . 135.3(10) ?
C8A C7 C11 C12 . . . . 155.9(10) ?
N1 C7 C11 C10B . . . . 143.2(13) ?
C8B C7 C11 C10B . . . . 7.6(16) ?
N1 C7 C11 C10A . . . . 148.9(15) ?
C8A C7 C11 C10A . . . . 33.9(18) ?
C16B C10B C11 C12 . . . . 68.(2) ?
C9B C10B C11 C12 . . . . -161.9(12) ?
C16B C10B C11 C7 . . . . -165.8(18) ?
C9B C10B C11 C7 . . . . -36.2(16) ?
C16A C10A C11 C12 . . . . 118.6(19) ?
C9A C10A C11 C12 . . . . -129.8(18) ?
C16A C10A C11 C7 . . . . -116.1(19) ?
C9A C10A C11 C7 . . . . -4.(2) ?
C7 C11 C12 O1 . . . . -46.9(11) ?
C10B C11 C12 O1 . . . . 73.0(14) ?
C10A C11 C12 O1 . . . . 76.1(14) ?
C7 C11 C12 C13 . . . . 133.7(8) ?
C10B C11 C12 C13 . . . . -106.4(13) ?
C10A C11 C12 C13 . . . . -103.3(13) ?
O1 C12 C13 N2 . . . . 177.2(8) ?
C11 C12 C13 N2 . . . . -3.4(11) ?
O1 C12 C13 N3 . . . . -2.1(13) ?
C11 C12 C13 N3 . . . . 177.3(7) ?
N2 C14 C15 N3 . . . . -2.4(11) ?
C1 C6 N1 C7 . . . . 163.5(8) ?
C5 C6 N1 C7 . . . . -19.3(12) ?
C11 C7 N1 C6 . . . . 160.7(7) ?
C8B C7 N1 C6 . . . . -70.7(13) ?
C8A C7 N1 C6 . . . . -87.5(13) ?
N3 C13 N2 C14 . . . . -2.1(10) ?
C12 C13 N2 C14 . . . . 178.5(8) ?
C15 C14 N2 C13 . . . . 2.8(11) ?
C14 C15 N3 C13 . . . . 0.9(10) ?
C14 C15 N3 C17 . . . . -178.5(10) ?
N2 C13 N3 C15 . . . . 0.8(10) ?
C12 C13 N3 C15 . . . . -179.8(8) ?
N2 C13 N3 C17 . . . . -179.7(9) ?
C12 C13 N3 C17 . . . . -0.4(14) ?

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
C5 H5 N2 2_656 0.94 2.52 3.364(10) 149.4 ?
C7 H7A^a O1 . 0.99 2.57 2.931(12) 101.6 ?
C11 H11A^a N2 . 0.99 2.47 2.935(10) 108.1 ?
N1 H1N O1 2_646 0.87 2.38 3.028(9) 131.8 ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Cyclohexane/chloroform'
####################################################################### 
# 
# 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_03327_1
_database_code_depnum_ccdc_archive 'CCDC 2111056'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles Hernaez'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2021-09-21 deposited with the CCDC.	2021-12-13 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            'LM-no lo se_150K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H21 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         283.37
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.0084(5)
_cell_length_b                   11.0369(6)
_cell_length_c                   13.3690(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1476.76(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7322
_cell_measurement_theta_min      2.3928
_cell_measurement_theta_max      23.9497
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.062
_exptl_crystal_size_min          0.045
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'sealed tube'
_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       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            30419
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         26.51
_diffrn_reflns_theta_full        26.51
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             3055
_reflns_number_gt                2691
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0902
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.2699P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_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         0.356
_refine_diff_density_min         -0.340
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)

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       ?
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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 0.4840(2) 0.5450(2) 0.44551(17) 0.0303(5) Uani d . . . 1 . .
H H1A 0.534202 0.474988 0.428199 0.036 Uiso calc U . R 1 . .
C C2 0.3869(3) 0.5371(2) 0.51856(18) 0.0351(6) Uani d . . . 1 . .
H H2 0.370125 0.461519 0.550143 0.042 Uiso calc U . R 1 . .
C C3 0.3137(2) 0.6379(2) 0.54635(17) 0.0326(6) Uani d . . . 1 . .
H H3 0.245497 0.63186 0.595543 0.039 Uiso calc U . R 1 . .
C C4 0.3416(2) 0.7469(2) 0.50127(18) 0.0300(5) Uani d . . . 1 . .
H H4 0.293688 0.817165 0.521212 0.036 Uiso calc U . R 1 . .
C C5 0.4383(2) 0.7568(2) 0.42729(16) 0.0272(5) Uani d . . . 1 . .
H H5 0.456225 0.833164 0.39743 0.033 Uiso calc U . R 1 . .
C C6 0.5093(2) 0.6544(2) 0.39678(16) 0.0237(5) Uani d . . . 1 . .
C C7 0.6061(2) 0.7456(2) 0.24198(16) 0.0249(5) Uani d . . . 1 . .
H H7 0.581524 0.82709 0.269047 0.03 Uiso calc U . R 1 . .
C C8 0.7444(2) 0.7519(2) 0.19067(19) 0.0312(5) Uani d . . . 1 . .
H H8A 0.772673 0.837314 0.182754 0.037 Uiso calc U . R 1 . .
H H8B 0.812061 0.709149 0.231579 0.037 Uiso calc U . R 1 . .
C C9 0.7311(2) 0.6912(2) 0.08811(17) 0.0312(5) Uani d . . . 1 . .
H H9A 0.734602 0.752469 0.034098 0.037 Uiso calc U . R 1 . .
H H9B 0.804075 0.632032 0.07761 0.037 Uiso calc U . R 1 . .
C C10 0.5963(2) 0.6276(2) 0.08868(17) 0.0277(5) Uani d . . . 1 . .
H H10 0.606361 0.548599 0.12455 0.033 Uiso calc U . R 1 . .
C C11 0.5118(2) 0.71187(19) 0.15329(16) 0.0234(5) Uani d . . . 1 . .
H H11 0.493431 0.787172 0.114029 0.028 Uiso calc U . R 1 . .
C C12 0.3810(2) 0.66067(18) 0.18718(16) 0.0230(5) Uani d . . . 1 . .
C C13 0.2805(2) 0.7478(2) 0.22286(15) 0.0221(5) Uani d . . . 1 . .
C C14 0.1823(2) 0.9118(2) 0.26355(18) 0.0307(5) Uani d . . . 1 . .
H H14 0.161414 0.995449 0.269991 0.037 Uiso calc U . R 1 . .
C C15 0.1085(2) 0.8204(2) 0.30234(17) 0.0300(5) Uani d . . . 1 . .
H H15 0.029171 0.828014 0.340893 0.036 Uiso calc U . R 1 . .
C C16 0.5390(3) 0.6028(3) -0.01422(18) 0.0422(6) Uani d . . . 1 . .
H H16A 0.452241 0.562375 -0.007407 0.063 Uiso calc U . R 1 . .
H H16B 0.600217 0.550447 -0.051682 0.063 Uiso calc U . R 1 . .
H H16C 0.527318 0.679486 -0.050103 0.063 Uiso calc U . R 1 . .
C C17 0.1281(3) 0.5953(2) 0.3081(2) 0.0362(6) Uani d . . . 1 . .
H H17A 0.046825 0.601776 0.348588 0.054 Uiso calc U . R 1 . .
H H17B 0.19945 0.558546 0.348049 0.054 Uiso calc U . R 1 . .
H H17C 0.110293 0.544682 0.249341 0.054 Uiso calc U . R 1 . .
N N1 0.60593(19) 0.65666(16) 0.32207(13) 0.0245(4) Uani d . . . 1 . .
H H1 0.669747 0.601833 0.323362 0.029 Uiso calc U . R 1 . .
N N2 0.29045(18) 0.86743(17) 0.21410(14) 0.0264(4) Uani d . . . 1 . .
N N3 0.16956(17) 0.71627(17) 0.27550(13) 0.0248(4) Uani d . . . 1 . .
O O1 0.35970(15) 0.55199(13) 0.18915(13) 0.0312(4) 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 C2 . 1.381(3) ?
C1 C6 . 1.395(3) ?
C2 C3 . 1.382(3) ?
C3 C4 . 1.375(4) ?
C4 C5 . 1.388(3) ?
C5 C6 . 1.395(3) ?
C6 N1 . 1.391(3) ?
C7 N1 . 1.453(3) ?
C7 C8 . 1.546(3) ?
C7 C11 . 1.561(3) ?
C8 C9 . 1.532(3) ?
C9 C10 . 1.520(3) ?
C10 C16 . 1.516(3) ?
C10 C11 . 1.525(3) ?
C11 C12 . 1.496(3) ?
C12 O1 . 1.219(2) ?
C12 C13 . 1.472(3) ?
C13 N2 . 1.329(3) ?
C13 N3 . 1.360(3) ?
C14 C15 . 1.354(3) ?
C14 N2 . 1.360(3) ?
C15 N3 . 1.350(3) ?
C17 N3 . 1.464(3) ?

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
C2 C1 C6 . . 120.8(2) ?
C1 C2 C3 . . 120.8(2) ?
C4 C3 C2 . . 118.6(2) ?
C3 C4 C5 . . 121.5(2) ?
C4 C5 C6 . . 120.0(2) ?
N1 C6 C1 . . 118.50(19) ?
N1 C6 C5 . . 123.3(2) ?
C1 C6 C5 . . 118.2(2) ?
N1 C7 C8 . . 111.00(18) ?
N1 C7 C11 . . 113.44(17) ?
C8 C7 C11 . . 102.41(17) ?
C9 C8 C7 . . 107.42(18) ?
C10 C9 C8 . . 105.95(18) ?
C16 C10 C9 . . 114.5(2) ?
C16 C10 C11 . . 114.5(2) ?
C9 C10 C11 . . 102.30(18) ?
C12 C11 C10 . . 115.23(18) ?
C12 C11 C7 . . 112.90(17) ?
C10 C11 C7 . . 103.92(17) ?
O1 C12 C13 . . 121.1(2) ?
O1 C12 C11 . . 122.1(2) ?
C13 C12 C11 . . 116.72(18) ?
N2 C13 N3 . . 111.20(19) ?
N2 C13 C12 . . 124.70(19) ?
N3 C13 C12 . . 123.95(19) ?
C15 C14 N2 . . 110.6(2) ?
N3 C15 C14 . . 106.6(2) ?
C6 N1 C7 . . 122.85(18) ?
C13 N2 C14 . . 104.79(19) ?
C15 N3 C13 . . 106.80(18) ?
C15 N3 C17 . . 124.66(18) ?
C13 N3 C17 . . 128.24(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.0(4) ?
C1 C2 C3 C4 . . . . -1.5(4) ?
C2 C3 C4 C5 . . . . 1.8(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C2 C1 C6 N1 . . . . -178.5(2) ?
C2 C1 C6 C5 . . . . 3.1(3) ?
C4 C5 C6 N1 . . . . 178.9(2) ?
C4 C5 C6 C1 . . . . -2.7(3) ?
N1 C7 C8 C9 . . . . 106.7(2) ?
C11 C7 C8 C9 . . . . -14.6(2) ?
C7 C8 C9 C10 . . . . -11.5(3) ?
C8 C9 C10 C16 . . . . 157.9(2) ?
C8 C9 C10 C11 . . . . 33.5(2) ?
C16 C10 C11 C12 . . . . 68.5(3) ?
C9 C10 C11 C12 . . . . -167.02(18) ?
C16 C10 C11 C7 . . . . -167.4(2) ?
C9 C10 C11 C7 . . . . -43.0(2) ?
N1 C7 C11 C12 . . . . 41.3(2) ?
C8 C7 C11 C12 . . . . 161.04(18) ?
N1 C7 C11 C10 . . . . -84.2(2) ?
C8 C7 C11 C10 . . . . 35.5(2) ?
C10 C11 C12 O1 . . . . 20.5(3) ?
C7 C11 C12 O1 . . . . -98.7(2) ?
C10 C11 C12 C13 . . . . -162.29(19) ?
C7 C11 C12 C13 . . . . 78.5(2) ?
O1 C12 C13 N2 . . . . -173.0(2) ?
C11 C12 C13 N2 . . . . 9.8(3) ?
O1 C12 C13 N3 . . . . 11.9(3) ?
C11 C12 C13 N3 . . . . -165.32(19) ?
N2 C14 C15 N3 . . . . -1.1(3) ?
C1 C6 N1 C7 . . . . 155.3(2) ?
C5 C6 N1 C7 . . . . -26.3(3) ?
C8 C7 N1 C6 . . . . 162.42(18) ?
C11 C7 N1 C6 . . . . -82.9(2) ?
N3 C13 N2 C14 . . . . 0.3(2) ?
C12 C13 N2 C14 . . . . -175.3(2) ?
C15 C14 N2 C13 . . . . 0.5(3) ?
C14 C15 N3 C13 . . . . 1.2(2) ?
C14 C15 N3 C17 . . . . 175.3(2) ?
N2 C13 N3 C15 . . . . -1.0(2) ?
C12 C13 N3 C15 . . . . 174.7(2) ?
N2 C13 N3 C17 . . . . -174.8(2) ?
C12 C13 N3 C17 . . . . 0.9(3) ?

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
N1 H1 N2 3_645 0.88 2.67 3.391(3) 140.6 ?
C7 H7 O1 3_655 1.00 2.61 3.521(3) 151.2 ?

