# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_cmhv7f3b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2374941'
loop_
_audit_author_name
_audit_author_address
'Estibaliz Merino'
;University of Alcala
Spain
;
_audit_update_record             
;
2024-07-31 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2022-03-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 F3 N2'
_chemical_formula_sum            'C19 H17 F3 N2'
_chemical_formula_weight         330.34
_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'
F F 0.0727 0.0534 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.541(10)
_cell_length_b                   10.615(6)
_cell_length_c                   10.654(8)
_cell_angle_alpha                119.18(5)
_cell_angle_beta                 95.86(5)
_cell_angle_gamma                104.41(7)
_cell_volume                     787.8(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      72.08
_cell_measurement_theta_min      4.84
_shelx_estimated_absorpt_T_max   0.915
_shelx_estimated_absorpt_T_min   0.840
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1044 before and 0.0664 after correction. The Ratio of minimum to maximum transmission is 0.8648. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20367
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.316
_diffrn_reflns_theta_min         4.842
_diffrn_ambient_temperature      220.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2791
_reflns_number_total             2954
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.063(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0613P)²+0.2911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C10(H10), C3(H3), C12(H12), C13(H13), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.28193(14) 0.42720(13) 0.70777(13) 0.0587(3) Uani 1 1 d . . . . .
F3 F 0.10245(14) 0.40947(14) 0.54102(13) 0.0650(4) Uani 1 1 d . . . . .
F1 F 0.16357(17) 0.59445(13) 0.76714(15) 0.0728(4) Uani 1 1 d . . . . .
N2 N 0.63682(14) 0.87355(13) 0.45693(12) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.73013(15) 0.89847(14) 0.58174(13) 0.0339(3) Uani 1 1 d . . . . .
C6 C 0.46120(16) 0.72332(15) 0.50262(14) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.47871(16) 0.77279(15) 0.40302(14) 0.0276(3) Uani 1 1 d . . . . .
C5 C 0.33178(17) 0.62361(15) 0.51776(15) 0.0296(3) Uani 1 1 d . . . . .
H5 H 0.225710 0.570634 0.448898 0.035 Uiso 1 1 calc R . . . .
C8 C 0.39415(17) 0.75849(15) 0.26328(14) 0.0292(3) Uani 1 1 d . . . . .
H8 H 0.296675 0.793510 0.278239 0.035 Uiso 1 1 calc R . . . .
C14 C 0.67631(18) 0.93679(15) 0.36907(15) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.62133(17) 0.80525(15) 0.61034(15) 0.0307(3) Uani 1 1 d . . . . .
C4 C 0.36522(18) 0.60630(15) 0.63564(15) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.65129(19) 0.78441(17) 0.73087(16) 0.0367(4) Uani 1 1 d . . . . .
H2 H 0.756070 0.836914 0.801574 0.044 Uiso 1 1 calc R . . . .
C9 C 0.53322(18) 0.87291(15) 0.25396(15) 0.0311(3) Uani 1 1 d . . . . .
C10 C 0.5378(2) 0.91492(17) 0.14994(17) 0.0374(4) Uani 1 1 d . . . . .
H10 H 0.443036 0.873998 0.070803 0.045 Uiso 1 1 calc R . . . .
C3 C 0.52424(19) 0.68621(17) 0.74185(16) 0.0359(4) Uani 1 1 d . . . . .
H3 H 0.542176 0.671033 0.821242 0.043 Uiso 1 1 calc R . . . .
C16 C 0.34019(18) 0.59671(16) 0.12126(15) 0.0330(3) Uani 1 1 d . . . . .
H16A H 0.310544 0.604349 0.034514 0.040 Uiso 1 1 calc R . . . .
H16B H 0.436327 0.561217 0.113062 0.040 Uiso 1 1 calc R . . . .
C12 C 0.8263(2) 1.08026(18) 0.28042(19) 0.0416(4) Uani 1 1 d . . . . .
H12 H 0.924537 1.150274 0.287508 0.050 Uiso 1 1 calc R . . . .
C17 C 0.19351(18) 0.47675(16) 0.11519(15) 0.0334(3) Uani 1 1 d . . . . .
H17A H 0.099408 0.514805 0.130943 0.040 Uiso 1 1 calc R . . . .
H17B H 0.225857 0.461372 0.196263 0.040 Uiso 1 1 calc R . . . .
C13 C 0.82480(19) 1.03978(16) 0.38671(17) 0.0374(4) Uani 1 1 d . . . . .
H13 H 0.919503 1.080347 0.465820 0.045 Uiso 1 1 calc R . . . .
C15 C 0.2294(2) 0.50969(17) 0.66111(17) 0.0373(4) Uani 1 1 d . . . . .
C18 C 0.1367(2) 0.32309(17) -0.03277(17) 0.0394(4) Uani 1 1 d . . . . .
H18A H 0.105998 0.339176 -0.113665 0.047 Uiso 1 1 calc R . . . .
H18B H 0.230874 0.285075 -0.047811 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6859(2) 1.01917(18) 0.16482(18) 0.0419(4) Uani 1 1 d . . . . .
H11 H 0.690393 1.048561 0.094728 0.050 Uiso 1 1 calc R . . . .
C19 C -0.0108(2) 0.20185(19) -0.0422(2) 0.0483(4) Uani 1 1 d . . . . .
H19A H -0.043985 0.108946 -0.140338 0.072 Uiso 1 1 calc GR . . . .
H19B H -0.103903 0.239382 -0.025149 0.072 Uiso 1 1 calc GR . . . .
H19C H 0.021084 0.179588 0.032833 0.072 Uiso 1 1 calc GR . . . .


_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
F2 C15 1.3377(19) . ?
F3 C15 1.327(3) . ?
F1 C15 1.339(2) . ?
N2 N1 1.345(2) . ?
N2 C7 1.349(3) . ?
N2 C14 1.4161(19) . ?
N1 C1 1.353(2) . ?
C6 C7 1.400(2) . ?
C6 C5 1.410(2) . ?
C6 C1 1.435(3) . ?
C7 C8 1.506(2) . ?
C5 H5 0.9400 . ?
C5 C4 1.368(2) . ?
C8 H8 0.9900 . ?
C8 C9 1.523(2) . ?
C8 C16 1.543(2) . ?
C14 C9 1.388(3) . ?
C14 C13 1.378(3) . ?
C1 C2 1.415(2) . ?
C4 C3 1.422(3) . ?
C4 C15 1.488(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.364(3) . ?
C9 C10 1.382(2) . ?
C10 H10 0.9400 . ?
C10 C11 1.393(3) . ?
C3 H3 0.9400 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 C17 1.518(3) . ?
C12 H12 0.9400 . ?
C12 C13 1.393(2) . ?
C12 C11 1.381(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 C18 1.524(3) . ?
C13 H13 0.9400 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 C19 1.515(3) . ?
C11 H11 0.9400 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C7 117.00(13) . . ?
N1 N2 C14 130.54(13) . . ?
C7 N2 C14 112.45(13) . . ?
N2 N1 C1 101.54(14) . . ?
C7 C6 C5 135.96(13) . . ?
C7 C6 C1 103.85(13) . . ?
C5 C6 C1 120.17(14) . . ?
N2 C7 C6 104.77(13) . . ?
N2 C7 C8 109.64(13) . . ?
C6 C7 C8 145.59(13) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 118.01(14) . . ?
C4 C5 H5 121.0 . . ?
C7 C8 H8 110.0 . . ?
C7 C8 C9 100.46(13) . . ?
C7 C8 C16 114.95(13) . . ?
C9 C8 H8 110.0 . . ?
C9 C8 C16 111.06(13) . . ?
C16 C8 H8 110.0 . . ?
C9 C14 N2 106.52(14) . . ?
C13 C14 N2 129.23(14) . . ?
C13 C14 C9 124.25(15) . . ?
N1 C1 C6 112.84(14) . . ?
N1 C1 C2 126.96(14) . . ?
C2 C1 C6 120.20(14) . . ?
C5 C4 C3 121.98(14) . . ?
C5 C4 C15 119.79(15) . . ?
C3 C4 C15 118.11(15) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.29(15) . . ?
C3 C2 H2 120.9 . . ?
C14 C9 C8 110.88(14) . . ?
C10 C9 C8 130.51(14) . . ?
C10 C9 C14 118.56(15) . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.62(15) . . ?
C11 C10 H10 120.7 . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.34(15) . . ?
C2 C3 H3 119.3 . . ?
C8 C16 H16A 108.5 . . ?
C8 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C8 115.02(14) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.08(16) . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C16 C17 C18 112.61(14) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C14 C13 C12 116.10(15) . . ?
C14 C13 H13 121.9 . . ?
C12 C13 H13 121.9 . . ?
F2 C15 F1 104.91(14) . . ?
F2 C15 C4 113.23(15) . . ?
F3 C15 F2 105.80(15) . . ?
F3 C15 F1 106.35(17) . . ?
F3 C15 C4 113.82(15) . . ?
F1 C15 C4 112.03(14) . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 C17 113.63(15) . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.38(16) . . ?
C12 C11 H11 119.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 C6 -0.02(15) . . . . ?
N2 N1 C1 C2 -179.71(14) . . . . ?
N2 C7 C8 C9 -1.53(13) . . . . ?
N2 C7 C8 C16 117.74(15) . . . . ?
N2 C14 C9 C8 -1.76(15) . . . . ?
N2 C14 C9 C10 -179.62(12) . . . . ?
N2 C14 C13 C12 179.40(13) . . . . ?
N1 N2 C7 C6 0.27(16) . . . . ?
N1 N2 C7 C8 -179.54(11) . . . . ?
N1 N2 C14 C9 -179.10(13) . . . . ?
N1 N2 C14 C13 1.7(2) . . . . ?
N1 C1 C2 C3 179.13(13) . . . . ?
C6 C7 C8 C9 178.80(18) . . . . ?
C6 C7 C8 C16 -61.9(2) . . . . ?
C6 C5 C4 C3 0.5(2) . . . . ?
C6 C5 C4 C15 176.31(12) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C7 N2 N1 C1 -0.16(15) . . . . ?
C7 N2 C14 C9 0.73(15) . . . . ?
C7 N2 C14 C13 -178.45(14) . . . . ?
C7 C6 C5 C4 -179.36(14) . . . . ?
C7 C6 C1 N1 0.17(15) . . . . ?
C7 C6 C1 C2 179.88(12) . . . . ?
C7 C8 C9 C14 2.01(14) . . . . ?
C7 C8 C9 C10 179.53(14) . . . . ?
C7 C8 C16 C17 70.92(17) . . . . ?
C5 C6 C7 N2 178.20(14) . . . . ?
C5 C6 C7 C8 -2.1(3) . . . . ?
C5 C6 C1 N1 -178.58(12) . . . . ?
C5 C6 C1 C2 1.1(2) . . . . ?
C5 C4 C3 C2 0.1(2) . . . . ?
C5 C4 C15 F2 141.77(14) . . . . ?
C5 C4 C15 F3 20.88(19) . . . . ?
C5 C4 C15 F1 -99.82(18) . . . . ?
C8 C9 C10 C11 -177.19(13) . . . . ?
C8 C16 C17 C18 175.24(12) . . . . ?
C14 N2 N1 C1 179.67(13) . . . . ?
C14 N2 C7 C6 -179.59(10) . . . . ?
C14 N2 C7 C8 0.61(15) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C1 C6 C7 N2 -0.24(14) . . . . ?
C1 C6 C7 C8 179.43(18) . . . . ?
C1 C6 C5 C4 -1.11(19) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C9 C8 C16 C17 -175.89(11) . . . . ?
C9 C14 C13 C12 0.3(2) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C3 C4 C15 F2 -42.28(18) . . . . ?
C3 C4 C15 F3 -163.17(14) . . . . ?
C3 C4 C15 F1 76.13(19) . . . . ?
C16 C8 C9 C14 -120.04(14) . . . . ?
C16 C8 C9 C10 57.5(2) . . . . ?
C16 C17 C18 C19 -179.41(13) . . . . ?
C13 C14 C9 C8 177.47(12) . . . . ?
C13 C14 C9 C10 -0.4(2) . . . . ?
C13 C12 C11 C10 -0.1(2) . . . . ?
C15 C4 C3 C2 -175.79(13) . . . . ?
C11 C12 C13 C14 -0.1(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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2374943'
loop_
_audit_author_name
_audit_author_address
'Estibaliz Merino'
;University of Alcala
Spain
;
_audit_update_record             
;
2024-07-31 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2022-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Br N2'
_chemical_formula_sum            'C18 H15 Br N2'
_chemical_formula_weight         339.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6346(5)
_cell_length_b                   9.5012(7)
_cell_length_c                   10.3414(7)
_cell_angle_alpha                87.704(2)
_cell_angle_beta                 75.290(2)
_cell_angle_gamma                89.836(3)
_cell_volume                     724.95(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9307
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      72.60
_cell_measurement_theta_min      4.42
_shelx_estimated_absorpt_T_max   0.395
_shelx_estimated_absorpt_T_min   0.252
_exptl_absorpt_coefficient_mu    3.800
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1460 before and 0.0931 after correction. The Ratio of minimum to maximum transmission is 0.4634. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9760
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.756
_diffrn_reflns_theta_min         4.424
_diffrn_ambient_temperature      240.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2569
_reflns_number_total             2778
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.449
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0683
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0995P)²+1.8623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1774
_refine_ls_wR_factor_ref         0.1819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C8(H8), C13(H13), C5(H5), C4(H4), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.72367(7) 0.69767(5) 0.03976(4) 0.0473(3) Uani 1 1 d . . . . .
N2 N 0.8274(5) 0.3602(3) 0.5208(4) 0.0301(7) Uani 1 1 d . . . . .
N1 N 0.9023(5) 0.2292(4) 0.5135(4) 0.0354(8) Uani 1 1 d . . . . .
C1 C 0.8880(6) 0.1914(4) 0.6437(4) 0.0320(8) Uani 1 1 d . . . . .
C10 C 0.7314(5) 0.5742(4) 0.4291(4) 0.0282(8) Uani 1 1 d . . . . .
C6 C 0.8057(5) 0.2971(4) 0.7320(4) 0.0311(8) Uani 1 1 d . . . . .
C7 C 0.7684(5) 0.4067(4) 0.6481(4) 0.0292(8) Uani 1 1 d . . . . .
C14 C 0.8669(6) 0.3856(4) 0.2817(4) 0.0345(9) Uani 1 1 d . . . . .
H14 H 0.921453 0.296597 0.270793 0.041 Uiso 1 1 calc R . . . .
C15 C 0.8097(5) 0.4393(4) 0.4088(4) 0.0293(8) Uani 1 1 d . . . . .
C11 C 0.7097(5) 0.6513(4) 0.3151(4) 0.0299(8) Uani 1 1 d . . . . .
H11 H 0.658420 0.741628 0.323782 0.036 Uiso 1 1 calc R . . . .
C12 C 0.7633(5) 0.5947(4) 0.1914(4) 0.0313(8) Uani 1 1 d . . . . .
C8 C 0.6916(6) 0.5427(4) 0.6683(4) 0.0311(8) Uani 1 1 d . . . . .
H8 H 0.651651 0.574590 0.755679 0.037 Uiso 1 1 calc R . . . .
C16 C 0.5980(6) 0.7738(4) 0.5799(4) 0.0323(8) Uani 1 1 d . . . . .
H16A H 0.487896 0.776476 0.547648 0.039 Uiso 1 1 calc R . . . .
H16B H 0.685506 0.839484 0.522393 0.039 Uiso 1 1 calc R . . . .
C9 C 0.6750(5) 0.6276(4) 0.5632(4) 0.0311(8) Uani 1 1 d . . . . .
C13 C 0.8436(6) 0.4625(5) 0.1727(4) 0.0360(9) Uani 1 1 d . . . . .
H13 H 0.881228 0.426905 0.086612 0.043 Uiso 1 1 calc R . . . .
C5 C 0.7763(6) 0.2754(5) 0.8712(5) 0.0396(10) Uani 1 1 d . . . . .
H5 H 0.718698 0.344128 0.930074 0.047 Uiso 1 1 calc R . . . .
C4 C 0.8332(7) 0.1524(6) 0.9187(5) 0.0456(11) Uani 1 1 d . . . . .
H4 H 0.816176 0.136458 1.011431 0.055 Uiso 1 1 calc R . . . .
C2 C 0.9473(7) 0.0637(5) 0.6941(5) 0.0411(10) Uani 1 1 d . . . . .
H2 H 1.003959 -0.006663 0.636975 0.049 Uiso 1 1 calc R . . . .
C17 C 0.5519(7) 0.8262(4) 0.7211(5) 0.0382(10) Uani 1 1 d . . . . .
H17A H 0.661739 0.827513 0.753704 0.046 Uiso 1 1 calc R . . . .
H17B H 0.464780 0.761361 0.780106 0.046 Uiso 1 1 calc R . . . .
C3 C 0.9178(7) 0.0482(5) 0.8302(5) 0.0465(11) Uani 1 1 d . . . . .
H3 H 0.955429 -0.035437 0.866397 0.056 Uiso 1 1 calc R . . . .
C18 C 0.4721(8) 0.9731(5) 0.7265(6) 0.0515(12) Uani 1 1 d . . . . .
H18A H 0.557579 1.037235 0.667357 0.077 Uiso 1 1 calc GR . . . .
H18B H 0.447330 1.004781 0.817328 0.077 Uiso 1 1 calc GR . . . .
H18C H 0.360342 0.971138 0.698204 0.077 Uiso 1 1 calc GR . . . .


_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
Br1 C12 1.904(4) . ?
N2 N1 1.365(4) . ?
N2 C7 1.370(5) . ?
N2 C15 1.391(5) . ?
N1 C1 1.357(6) . ?
C1 C6 1.420(6) . ?
C1 C2 1.419(6) . ?
C10 C15 1.413(5) . ?
C10 C11 1.409(6) . ?
C10 C9 1.455(6) . ?
C6 C7 1.403(5) . ?
C6 C5 1.407(6) . ?
C7 C8 1.419(5) . ?
C14 H14 0.9400 . ?
C14 C15 1.393(6) . ?
C14 C13 1.367(6) . ?
C11 H11 0.9400 . ?
C11 C12 1.372(6) . ?
C12 C13 1.394(6) . ?
C8 H8 0.9400 . ?
C8 C9 1.359(6) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 C9 1.506(5) . ?
C16 C17 1.517(6) . ?
C13 H13 0.9400 . ?
C5 H5 0.9400 . ?
C5 C4 1.363(7) . ?
C4 H4 0.9400 . ?
C4 C3 1.416(8) . ?
C2 H2 0.9400 . ?
C2 C3 1.369(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 C18 1.519(6) . ?
C3 H3 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 C7 114.4(3) . . ?
N1 N2 C15 123.0(3) . . ?
C7 N2 C15 122.6(3) . . ?
C1 N1 N2 103.0(3) . . ?
N1 C1 C6 112.5(3) . . ?
N1 C1 C2 126.9(4) . . ?
C2 C1 C6 120.6(4) . . ?
C15 C10 C9 120.3(3) . . ?
C11 C10 C15 117.0(4) . . ?
C11 C10 C9 122.6(3) . . ?
C7 C6 C1 104.7(4) . . ?
C7 C6 C5 134.7(4) . . ?
C5 C6 C1 120.6(4) . . ?
N2 C7 C6 105.5(3) . . ?
N2 C7 C8 119.6(3) . . ?
C6 C7 C8 135.0(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
N2 C15 C10 117.7(4) . . ?
N2 C15 C14 120.5(3) . . ?
C14 C15 C10 121.8(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 Br1 119.2(3) . . ?
C11 C12 C13 122.2(4) . . ?
C13 C12 Br1 118.5(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
H16A C16 H16B 107.4 . . ?
C9 C16 H16A 108.3 . . ?
C9 C16 H16B 108.3 . . ?
C9 C16 C17 116.0(3) . . ?
C17 C16 H16A 108.3 . . ?
C17 C16 H16B 108.3 . . ?
C10 C9 C16 118.6(3) . . ?
C8 C9 C10 118.6(4) . . ?
C8 C9 C16 122.8(4) . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.8 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.8(5) . . ?
C3 C4 H4 119.6 . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 116.7(5) . . ?
C3 C2 H2 121.7 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C16 C17 C18 111.4(4) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C4 C3 H3 118.5 . . ?
C2 C3 C4 123.0(4) . . ?
C2 C3 H3 118.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C12 C13 C14 -177.7(3) . . . . ?
N2 N1 C1 C6 -0.2(4) . . . . ?
N2 N1 C1 C2 -179.3(4) . . . . ?
N2 C7 C8 C9 0.3(6) . . . . ?
N1 N2 C7 C6 -0.6(5) . . . . ?
N1 N2 C7 C8 178.6(4) . . . . ?
N1 N2 C15 C10 -179.4(4) . . . . ?
N1 N2 C15 C14 0.9(6) . . . . ?
N1 C1 C6 C7 -0.2(5) . . . . ?
N1 C1 C6 C5 178.7(4) . . . . ?
N1 C1 C2 C3 -179.7(4) . . . . ?
C1 C6 C7 N2 0.4(4) . . . . ?
C1 C6 C7 C8 -178.6(4) . . . . ?
C1 C6 C5 C4 1.8(6) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C10 C11 C12 Br1 177.5(3) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C6 C1 C2 C3 1.1(7) . . . . ?
C6 C7 C8 C9 179.2(4) . . . . ?
C6 C5 C4 C3 -0.8(7) . . . . ?
C7 N2 N1 C1 0.5(5) . . . . ?
C7 N2 C15 C10 1.6(6) . . . . ?
C7 N2 C15 C14 -178.0(4) . . . . ?
C7 C6 C5 C4 -179.6(5) . . . . ?
C7 C8 C9 C10 2.3(6) . . . . ?
C7 C8 C9 C16 -178.6(4) . . . . ?
C15 N2 N1 C1 -178.6(4) . . . . ?
C15 N2 C7 C6 178.5(3) . . . . ?
C15 N2 C7 C8 -2.3(6) . . . . ?
C15 C10 C11 C12 0.1(6) . . . . ?
C15 C10 C9 C8 -2.9(6) . . . . ?
C15 C10 C9 C16 177.9(4) . . . . ?
C15 C14 C13 C12 0.4(6) . . . . ?
C11 C10 C15 N2 -178.2(3) . . . . ?
C11 C10 C15 C14 1.4(6) . . . . ?
C11 C10 C9 C8 176.3(4) . . . . ?
C11 C10 C9 C16 -2.9(6) . . . . ?
C11 C12 C13 C14 1.2(7) . . . . ?
C9 C10 C15 N2 1.0(6) . . . . ?
C9 C10 C15 C14 -179.3(4) . . . . ?
C9 C10 C11 C12 -179.1(4) . . . . ?
C9 C16 C17 C18 -178.8(4) . . . . ?
C13 C14 C15 N2 178.0(4) . . . . ?
C13 C14 C15 C10 -1.7(6) . . . . ?
C5 C6 C7 N2 -178.3(5) . . . . ?
C5 C6 C7 C8 2.7(8) . . . . ?
C5 C4 C3 C2 0.0(8) . . . . ?
C2 C1 C6 C7 179.1(4) . . . . ?
C2 C1 C6 C5 -2.0(6) . . . . ?
C17 C16 C9 C10 -176.6(4) . . . . ?
C17 C16 C9 C8 4.3(6) . . . . ?

_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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2374942'
loop_
_audit_author_name
_audit_author_address
'Estibaliz Merino'
;University of Alcala
Spain
;
_audit_update_record             
;
2024-07-31 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_audit_creation_date             2023-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 N2 O4'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_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'

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

_cell_length_a                   10.3106(4)
_cell_length_b                   27.0052(10)
_cell_length_c                   7.1569(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.419(3)
_cell_angle_gamma                90
_cell_volume                     1929.99(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4199
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      71.70
_cell_measurement_theta_min      5.51
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0892 before and 0.0609 after correction. The Ratio of minimum to maximum transmission is 0.8633. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.272
_diffrn_reflns_theta_min         5.510
_diffrn_ambient_temperature      299.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2272
_reflns_number_total             3793
_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    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0943P)²+0.5236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1999
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C8(H8A,H8B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C2(H2), C5(H5), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.08804(19) 0.36393(7) 0.2855(3) 0.0566(5) Uani 1 1 d . . . . .
O4 O -0.03605(17) 0.18537(6) 0.2684(3) 0.0725(5) Uani 1 1 d . . . . .
O3 O 0.15432(19) 0.14278(6) 0.3095(3) 0.0791(6) Uani 1 1 d . . . . .
N2 N -0.0422(2) 0.36409(7) 0.2964(3) 0.0641(6) Uani 1 1 d . . . . .
O2 O 0.5656(2) 0.22920(8) 0.4496(4) 0.1121(9) Uani 1 1 d . . . . .
C15 C 0.1610(2) 0.31908(7) 0.3041(3) 0.0514(5) Uani 1 1 d . . . . .
C14 C 0.0925(2) 0.27483(8) 0.2889(3) 0.0527(6) Uani 1 1 d . . . . .
H14 H -0.000462 0.274608 0.263892 0.063 Uiso 1 1 calc R . . . .
C13 C 0.1630(2) 0.23082(8) 0.3110(3) 0.0530(6) Uani 1 1 d . . . . .
C10 C 0.3010(2) 0.32190(8) 0.3414(3) 0.0551(6) Uani 1 1 d . . . . .
C12 C 0.3013(2) 0.23195(8) 0.3511(4) 0.0571(6) Uani 1 1 d . . . . .
H12 H 0.348797 0.202321 0.366976 0.069 Uiso 1 1 calc R . . . .
C11 C 0.3711(2) 0.27670(8) 0.3680(4) 0.0586(6) Uani 1 1 d . . . . .
C9 C 0.3679(2) 0.37253(9) 0.3629(4) 0.0628(6) Uani 1 1 d . . . . .
H9 H 0.449733 0.369800 0.317354 0.075 Uiso 1 1 calc R . . . .
C18 C 0.0960(2) 0.18181(8) 0.2958(3) 0.0575(6) Uani 1 1 d . . . . .
O1 O 0.5950(2) 0.30821(10) 0.4430(6) 0.1453(13) Uani 1 1 d . . . . .
C20 C 0.4090(3) 0.38671(10) 0.5767(4) 0.0696(7) Uani 1 1 d . . . . .
H20A H 0.329144 0.395617 0.617630 0.084 Uiso 1 1 calc R . . . .
H20B H 0.448080 0.357941 0.650783 0.084 Uiso 1 1 calc R . . . .
C7 C 0.1390(3) 0.40894(8) 0.2623(4) 0.0619(6) Uani 1 1 d . . . . .
C8 C 0.2780(3) 0.41151(9) 0.2387(4) 0.0723(7) Uani 1 1 d . . . . .
H8A H 0.314408 0.444230 0.275140 0.087 Uiso 1 1 calc R . . . .
H8B H 0.276789 0.406253 0.104164 0.087 Uiso 1 1 calc R . . . .
C16 C 0.5201(3) 0.27433(10) 0.4201(5) 0.0749(8) Uani 1 1 d . . . . .
C1 C -0.0734(3) 0.41266(9) 0.2803(4) 0.0650(7) Uani 1 1 d . . . . .
C6 C 0.0359(3) 0.44233(9) 0.2586(3) 0.0666(7) Uani 1 1 d . . . . .
C19 C -0.1086(3) 0.13906(10) 0.2512(5) 0.0802(8) Uani 1 1 d . . . . .
H19A H -0.077012 0.117300 0.166033 0.120 Uiso 1 1 calc GR . . . .
H19B H -0.202446 0.145218 0.200105 0.120 Uiso 1 1 calc GR . . . .
H19C H -0.094451 0.123923 0.376025 0.120 Uiso 1 1 calc GR . . . .
C2 C -0.1963(3) 0.43475(11) 0.2877(4) 0.0812(9) Uani 1 1 d . . . . .
H2 H -0.268079 0.415873 0.304043 0.097 Uiso 1 1 calc R . . . .
C5 C 0.0207(3) 0.49442(10) 0.2408(4) 0.0818(9) Uani 1 1 d . . . . .
H5 H 0.090836 0.514332 0.225196 0.098 Uiso 1 1 calc R . . . .
C4 C -0.0979(4) 0.51435(12) 0.2471(4) 0.0937(11) Uani 1 1 d . . . . .
H4 H -0.109156 0.548484 0.235956 0.112 Uiso 1 1 calc R . . . .
C21 C 0.5073(3) 0.42895(12) 0.6235(5) 0.0947(10) Uani 1 1 d . . . . .
H21A H 0.464691 0.458784 0.561660 0.114 Uiso 1 1 calc R . . . .
H21B H 0.583042 0.421758 0.570251 0.114 Uiso 1 1 calc R . . . .
C3 C -0.2048(4) 0.48490(12) 0.2699(5) 0.0941(11) Uani 1 1 d . . . . .
H3 H -0.284926 0.500269 0.272953 0.113 Uiso 1 1 calc R . . . .
C17 C 0.7080(3) 0.22128(14) 0.5107(7) 0.1228(15) Uani 1 1 d . . . . .
H17A H 0.743267 0.217058 0.399586 0.184 Uiso 1 1 calc GR . . . .
H17B H 0.726007 0.192132 0.589746 0.184 Uiso 1 1 calc GR . . . .
H17C H 0.749813 0.249380 0.583655 0.184 Uiso 1 1 calc GR . . . .
C22 C 0.5576(4) 0.43838(15) 0.8371(6) 0.1296(15) Uani 1 1 d . . . . .
H22A H 0.609331 0.468342 0.857407 0.194 Uiso 1 1 calc GR . . . .
H22B H 0.612685 0.411165 0.896175 0.194 Uiso 1 1 calc GR . . . .
H22C H 0.482845 0.441628 0.893721 0.194 Uiso 1 1 calc GR . . . .


_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
N1 N2 1.364(3) . ?
N1 C15 1.415(3) . ?
N1 C7 1.351(3) . ?
O4 C18 1.330(3) . ?
O4 C19 1.447(3) . ?
O3 C18 1.205(3) . ?
N2 C1 1.349(3) . ?
O2 C16 1.304(3) . ?
O2 C17 1.440(4) . ?
C15 C14 1.379(3) . ?
C15 C10 1.402(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C13 C12 1.383(3) . ?
C13 C18 1.484(3) . ?
C10 C11 1.407(3) . ?
C10 C9 1.522(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.396(3) . ?
C11 C16 1.490(4) . ?
C9 H9 0.9800 . ?
C9 C20 1.531(4) . ?
C9 C8 1.533(3) . ?
O1 C16 1.182(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.507(4) . ?
C7 C8 1.486(4) . ?
C7 C6 1.389(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 C6 1.422(4) . ?
C1 C2 1.413(4) . ?
C6 C5 1.418(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C3 1.361(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.347(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.401(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(5) . ?
C3 H3 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N2 N1 C15 120.35(18) . . ?
C7 N1 N2 115.02(19) . . ?
C7 N1 C15 124.6(2) . . ?
C18 O4 C19 116.02(19) . . ?
C1 N2 N1 102.4(2) . . ?
C16 O2 C17 119.1(3) . . ?
C14 C15 N1 119.0(2) . . ?
C14 C15 C10 123.0(2) . . ?
C10 C15 N1 117.99(19) . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C14 C13 C12 119.4(2) . . ?
C14 C13 C18 122.5(2) . . ?
C12 C13 C18 118.1(2) . . ?
C15 C10 C11 116.6(2) . . ?
C15 C10 C9 119.2(2) . . ?
C11 C10 C9 124.1(2) . . ?
C13 C12 H12 119.4 . . ?
C13 C12 C11 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C10 C11 C16 122.3(2) . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 C16 117.5(2) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C20 109.3(2) . . ?
C10 C9 C8 111.4(2) . . ?
C20 C9 H9 107.8 . . ?
C20 C9 C8 112.6(2) . . ?
C8 C9 H9 107.8 . . ?
O4 C18 C13 112.76(19) . . ?
O3 C18 O4 123.1(2) . . ?
O3 C18 C13 124.1(2) . . ?
C9 C20 H20A 108.6 . . ?
C9 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 C9 114.5(2) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
N1 C7 C8 118.2(2) . . ?
N1 C7 C6 105.5(2) . . ?
C6 C7 C8 136.3(2) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C7 C8 C9 111.3(2) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O2 C16 C11 112.8(2) . . ?
O1 C16 O2 120.3(3) . . ?
O1 C16 C11 126.8(3) . . ?
N2 C1 C6 112.2(2) . . ?
N2 C1 C2 127.2(3) . . ?
C2 C1 C6 120.6(2) . . ?
C7 C6 C1 104.8(2) . . ?
C7 C6 C5 135.5(3) . . ?
C5 C6 C1 119.7(3) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 H2 121.5 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.3(3) . . ?
C4 C5 H5 120.8 . . ?
C5 C4 H4 119.2 . . ?
C5 C4 C3 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C20 C21 C22 113.3(3) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C2 C3 C4 122.8(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C1 C6 0.3(3) . . . . ?
N1 N2 C1 C2 -178.1(2) . . . . ?
N1 C15 C14 C13 -178.6(2) . . . . ?
N1 C15 C10 C11 177.2(2) . . . . ?
N1 C15 C10 C9 0.9(3) . . . . ?
N1 C7 C8 C9 -36.2(3) . . . . ?
N1 C7 C6 C1 -0.2(3) . . . . ?
N1 C7 C6 C5 179.3(3) . . . . ?
N2 N1 C15 C14 14.8(3) . . . . ?
N2 N1 C15 C10 -163.9(2) . . . . ?
N2 N1 C7 C8 -176.8(2) . . . . ?
N2 N1 C7 C6 0.5(3) . . . . ?
N2 C1 C6 C7 -0.1(3) . . . . ?
N2 C1 C6 C5 -179.7(2) . . . . ?
N2 C1 C2 C3 179.4(3) . . . . ?
C15 N1 N2 C1 177.6(2) . . . . ?
C15 N1 C7 C8 5.2(3) . . . . ?
C15 N1 C7 C6 -177.5(2) . . . . ?
C15 C14 C13 C12 1.0(4) . . . . ?
C15 C14 C13 C18 -179.8(2) . . . . ?
C15 C10 C11 C12 1.9(4) . . . . ?
C15 C10 C11 C16 -176.3(2) . . . . ?
C15 C10 C9 C20 94.0(3) . . . . ?
C15 C10 C9 C8 -31.1(3) . . . . ?
C14 C15 C10 C11 -1.5(3) . . . . ?
C14 C15 C10 C9 -177.8(2) . . . . ?
C14 C13 C12 C11 -0.5(4) . . . . ?
C14 C13 C18 O4 -3.0(3) . . . . ?
C14 C13 C18 O3 178.0(2) . . . . ?
C13 C12 C11 C10 -1.0(4) . . . . ?
C13 C12 C11 C16 177.3(2) . . . . ?
C10 C15 C14 C13 0.0(4) . . . . ?
C10 C11 C16 O2 176.1(3) . . . . ?
C10 C11 C16 O1 -0.6(5) . . . . ?
C10 C9 C20 C21 164.6(2) . . . . ?
C10 C9 C8 C7 47.2(3) . . . . ?
C12 C13 C18 O4 176.3(2) . . . . ?
C12 C13 C18 O3 -2.7(4) . . . . ?
C12 C11 C16 O2 -2.2(4) . . . . ?
C12 C11 C16 O1 -178.9(3) . . . . ?
C11 C10 C9 C20 -82.0(3) . . . . ?
C11 C10 C9 C8 152.9(2) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C11 C16 -0.2(4) . . . . ?
C9 C20 C21 C22 -173.6(3) . . . . ?
C18 C13 C12 C11 -179.8(2) . . . . ?
C20 C9 C8 C7 -76.0(3) . . . . ?
C7 N1 N2 C1 -0.5(3) . . . . ?
C7 N1 C15 C14 -167.3(2) . . . . ?
C7 N1 C15 C10 14.0(3) . . . . ?
C7 C6 C5 C4 -178.8(3) . . . . ?
C8 C9 C20 C21 -71.0(3) . . . . ?
C8 C7 C6 C1 176.3(3) . . . . ?
C8 C7 C6 C5 -4.2(5) . . . . ?
C1 C6 C5 C4 0.7(4) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C6 C7 C8 C9 147.6(3) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C5 C4 C3 -0.2(4) . . . . ?
C19 O4 C18 O3 -1.3(4) . . . . ?
C19 O4 C18 C13 179.7(2) . . . . ?
C2 C1 C6 C7 178.5(2) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C17 O2 C16 C11 -176.9(3) . . . . ?
C17 O2 C16 O1 0.1(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
